WO1999059978A1 - Substituted nitrogen heterocycles and their use as pesticides - Google Patents
Substituted nitrogen heterocycles and their use as pesticides Download PDFInfo
- Publication number
- WO1999059978A1 WO1999059978A1 PCT/EP1999/003092 EP9903092W WO9959978A1 WO 1999059978 A1 WO1999059978 A1 WO 1999059978A1 EP 9903092 W EP9903092 W EP 9903092W WO 9959978 A1 WO9959978 A1 WO 9959978A1
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- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- substituted
- radicals
- hydrogen
- cycloalkyl
- Prior art date
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 229910052757 nitrogen Inorganic materials 0.000 title claims abstract description 20
- 239000000575 pesticide Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 150000001449 anionic compounds Chemical class 0.000 claims abstract description 5
- 150000002891 organic anions Chemical class 0.000 claims abstract description 5
- 230000000749 insecticidal effect Effects 0.000 claims abstract description 4
- -1 hydroxy, cyano, nitro, thiocyanato Chemical group 0.000 claims description 320
- 229910052760 oxygen Inorganic materials 0.000 claims description 164
- 150000003254 radicals Chemical class 0.000 claims description 162
- 229910052736 halogen Inorganic materials 0.000 claims description 153
- 150000002367 halogens Chemical group 0.000 claims description 152
- 239000001257 hydrogen Substances 0.000 claims description 146
- 229910052739 hydrogen Inorganic materials 0.000 claims description 146
- 125000003118 aryl group Chemical group 0.000 claims description 132
- 125000001424 substituent group Chemical group 0.000 claims description 119
- 229910052731 fluorine Inorganic materials 0.000 claims description 116
- 239000011737 fluorine Substances 0.000 claims description 115
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 107
- 229910052717 sulfur Inorganic materials 0.000 claims description 88
- 239000001301 oxygen Substances 0.000 claims description 81
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 78
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 76
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 74
- 125000000623 heterocyclic group Chemical group 0.000 claims description 74
- 125000004122 cyclic group Chemical group 0.000 claims description 57
- 150000002431 hydrogen Chemical group 0.000 claims description 54
- 239000004215 Carbon black (E152) Substances 0.000 claims description 52
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 47
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 47
- 125000005842 heteroatom Chemical group 0.000 claims description 46
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 125000001072 heteroaryl group Chemical group 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 229930195733 hydrocarbon Natural products 0.000 claims description 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 22
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 20
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 20
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 20
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 20
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 19
- 125000002252 acyl group Chemical group 0.000 claims description 19
- 239000000460 chlorine Chemical group 0.000 claims description 19
- 229910052801 chlorine Chemical group 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 18
- 125000004104 aryloxy group Chemical group 0.000 claims description 18
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 18
- 125000001188 haloalkyl group Chemical group 0.000 claims description 18
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 18
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 13
- 239000011593 sulfur Substances 0.000 claims description 13
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 12
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 12
- 125000005110 aryl thio group Chemical group 0.000 claims description 12
- 150000001721 carbon Chemical group 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
- 125000004468 heterocyclylthio group Chemical group 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000003107 substituted aryl group Chemical group 0.000 claims description 11
- HEOQXHNKRXRCTO-UHFFFAOYSA-N 6,7,8,9-tetrahydro-5h-benzo[7]annulene Chemical compound C1CCCCC2=CC=CC=C21 HEOQXHNKRXRCTO-UHFFFAOYSA-N 0.000 claims description 10
- 150000002430 hydrocarbons Chemical group 0.000 claims description 10
- XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- 125000006413 ring segment Chemical group 0.000 claims description 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical group C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 claims description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 9
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- 238000006467 substitution reaction Methods 0.000 claims description 8
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- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 7
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 241000238631 Hexapoda Species 0.000 claims description 6
- 230000000895 acaricidal effect Effects 0.000 claims description 6
- 125000003435 aroyl group Chemical group 0.000 claims description 6
- 125000005333 aroyloxy group Chemical group 0.000 claims description 6
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
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- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 6
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 5
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 5
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- 238000000034 method Methods 0.000 claims description 5
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
- A01N57/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34 containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
Definitions
- the invention relates to novel substituted pyridines and pyrimidines and condensed systems derived therefrom, processes for their preparation and their use as pesticides, especially insecticides and acaricides.
- radicals and groups are as defined below, which, while showing good tolerance by plants and favourable toxicity in respect of warm-blooded animals, are highly suitable for controlling insects and acarids.
- the invention therefore relates to compounds of the formula I in which
- A is CH and D is N + R or
- A is nitrogen and D is N + R or
- A is N + R and D is nitrogen, where
- R is CR R 5 D a R 6 , (2) Q n " is an inorganic or organic anion, n being 1 , 2, 3 or 4;
- R 1 is hydrogen, halogen, (C-i-Csr-alkyl, (C ⁇ -C8)-haloalkyl, (C ⁇ -C8)-alkoxy or
- R 2 and R 3 are identical or different and are each hydrogen, (Ci-Csr-alkyl,
- R2 and R 3 together with the carbon atoms to which they are attached form an unsaturated 5- or 6-membered carbocyclic ring which may, if it is a 5-membered ring, contain an oxygen or sulfur atom instead of CH2, or which may, if it is a 6-membered ring, contain one or two nitrogen atoms instead of one or two CH units, and which may be substituted by 1, 2 or 3 identical or different radicals, these radicals being (C-J-C4)- alkyl, (C ⁇ -C4)-haloalkyl, preferably trifluoromethyl, halogen, (C1-C4)- alkoxy or (C ⁇ -C4)-haloalkoxy; or
- R 2 and R 3 together with the carbon atoms to which they are attached form a saturated 5-, 6- or 7-membered carbocyclic ring which may contain oxygen and/or sulfur instead of one or two CH2 groups and which may be substituted by 1, 2 or 3 (C-
- Y - Z together are a (C 1 -C2 ⁇ )-hy drocarD ⁇ n radical which is straight-chain or branched and in which one or more, preferably up to three, CH2 may be replaced by hetero atom radicals such as O, NR 10 , S, SO, SO2 or
- SiR 1 1 R 12 where R 10 is hydrogen, (C ⁇ -C4)-alkyl or (C-
- R 11 and R 12 are identical or different and are each independently of the other (C-
- Y is a bond or a bivalent hydrocarbon chain having 1 to 6 carbon atoms which may be substituted by one or more, preferably up to three, identical or different radicals selected from the group consisting of
- Z is aryl or O-aryl, where aryl is preferably a naphthyl or phenyl group, heterocycyl or heterocyclyloxy, each of which may be substituted by one or more, preferably up to five, in particular up to three, identical or different radicals selected from the group consisting of halogen, (C3-C8)-cycloalkyl,
- R 13 is (C-
- R 14 , R ⁇ 5 and R ⁇ 6 are identical or different and are each independently of one another (C-
- R 17 and R 18 are identical or different and are each independently of the other hydrogen, (C ⁇ -C4)-alkyl and/or (C ⁇
- R 19 is (C ⁇ -C ⁇ o)- a 'kyl, phenyl or substituted phenyl; wherein (C-
- Y is a bond or a bivalent hydrocarbon chain having 1 to 6 carbon atoms, preferably methylene, which is substituted by one or more, preferably up to three, identical or different radicals selected from the group consisting of
- (10) Z is (C3-C8)-cycloalkyl or (C5-C8)-cycloalkenyl, where a CH2 group of the carbocycle may be replaced by NR 2 ⁇ ;
- R20 j s phenyl or substituted phenyl and the (C3-C8)-cycloalkyl or (C5- C ⁇ J-cycloalkenyl radical may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of (C ⁇ -C 8 )-alkyl,
- R 1 1, R 12 and where additionally 3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle and where these hydrocarbon radicals with or without these variations may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of hydroxyl, halogen, alkyl, haloalkyl, cycloalkyl, acyl, phenyl, substituted phenyl, optionally substituted heterocyclyl, phenylthio and substituted phenylthio; where heteroaryl may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents; where aryl is as defined under (8); where R 24 and R ⁇ are identical or different and are each independently of the other hydrogen, (C-
- R 23 are identical or different and are each independently of the others (C ⁇ -Ci8)-alkyl, (C-
- R 22 attached to silicon together to form a cycle, the silicon atom in this case being a ring atom of this cycle, and where additionally these (C ⁇ -C-
- each X "1 independently of the other is sulfur or oxygen;
- R z is hydrogen, (C ⁇ -C4)-alkyl, trifluoromethyl or (C-
- Ry is (C-
- -C2 ⁇ )- a lkyl, (C2-C2 ⁇ )- a 'kenyl, (C2-C2o)" a lkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals and where in the alkyl, alkenyl or alkynyl radicals mentioned one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O) x , where x 0, 1 or
- (C ⁇ -C4)-alkyl preferably methyl, and where additionally 3 to 12 atoms of these hydrocarbon radicals, which may be modified as above, may form a cycle and where these hydrocarbon radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of halogen, aryl, aryloxy, arylthio, (C3-C8)- cycloalkoxy, (C3-C8)-cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, (C3-C8)- cycloalkanoyl, (C2-C ⁇ 2)-haloalkanoyl, aroyl, aryl-(C ⁇ -C4)- alkanoyl, (C3-C8r-cycloalkyl-(C-
- (C-)-C8)-trialkylsilyl preferably (C-
- (C ⁇ -C8)-alkoxycarbonyl where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or where the ring system formed by Ry and R z , together with a further benzene ring or cyclohexane ring, forms a condensed ring system, preferably the indane, 1,2,3,4-tetrahydro- naphthalene, decahydronaphthalene or benzocycloheptane system and where the benzene ring in these condensed systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, where among the compounds where the carbon atom between the hetero atoms X ⁇ carries only the substituent Ry, the substituents X and Ry are preferably
- R z is hydrogen, (C-
- R31 and R 32 independently of the other are each hydrogen, hydroxyl, halogen, cyano, (C-
- -C4)-alkanoyl, (C-1-C4)- haloalkanoyl, (C ⁇ -C4)-haloalkoxy, (C1-C4)- alkylthio or (C ⁇ -C4)-haloalkylthio; m 1 is 0, 1, 2, 3 or 4, preferably 1 or 2; n 1 is 0, 1 , 2, 3 or 4, preferably 1 or 2; Z 1 is a direct bond, NR 33 , O, S(O) s where s 0, 1 or 2, OSO2,
- R36 a nd R37 are eaC (C ⁇ -C4)-alkyl or phenyl, preferably methyl;
- U is a direct bond, NR 38 or O;
- W is oxygen or sulfur, preferably oxygen
- V is a direct bond, NR 39 or oxygen, where R33 R34 R35 R38 a nd R 39 are identical or different and are each hydrogen, alkyl, alkoxy, alkanoyl or cycloalkyl;
- R°. are substituents which are independent of one another and each is halogen, cyano, nitro, (C ⁇ -C2 ⁇ )-alkyl, (C2-C2o)-alkenyl,
- R°. is aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D 2 R 44 , or two adjacent radicals zl-R 0 - may combine with the carbon atoms to which they are attached to form a fused cycle having 4 to 6 ring atoms which is carbocyclic or contains hetero ring atoms selected from the group consisting of O, S and N and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C-
- R 33 , R 3 ⁇ or R 39 independently of one another may combine with the
- R°. located at Z to form a 4- to 8-membered ring system in which one or two CH2 groups, preferably one CH2 group, may be replaced by hetero atom units such as oxygen, S(O)t ⁇ where t
- R 40 is hydrogen, (C ⁇ -C4)-alkyl, (C-
- R 4 1 and R 42 independently of the other are each (C ⁇
- SiR 47 R 48 , and k 0, 1 or 2, where R46 independently of the others is hydrogen, (C ⁇ -C4)-alkyl, (C1-C4)- alkanoyl or (C3-C5)-cycloalkyl;
- R 47 and R 48 independently of the other are each (C-
- R 49 is (C ⁇ -C )-alkyl, (C 1 -C 4 )-haloalkyl, (C-
- R 45 is hydrogen, (C- j -CsJ-alkyl, (C ⁇ -C4)-haloalkyl, (C-
- R 50 is (C ⁇ -C 4 )-alkyl, (C ⁇ -C4)-haloalkyl, (C-i ⁇ -alkoxy, (C-j ⁇ )- alkylthio, halogen or cyano; or, if not included in the above definitions,
- Y 4 is a direct bond or CH2
- R U and wl-Rt are substituents of the heteroaliphatic ring system, where
- R u is hydrogen, halogen, cyano, (C ⁇
- R* may be aryl or heterocyclyl, where both of these radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D 4 R 57 or
- R51 j s hydrogen, (Cf-C ⁇ alkyl, (C-
- R 51 is CONR 60 R 61 where
- R6° and R 6 ⁇ l independently of the other are each hydrogen, (C-1-C4)- alkyl or phenyl, where the phenyl group may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R ⁇ 2 , and R 62 and R 59 independently of the other are each (C 1 -C4)-alkyl, (C-
- C4)-haloalkyl (C-
- R52 J S hydrogen, (C ⁇ -C4)-alkyl, (C-j-O ⁇ -alkanoyl or (C3-C5)-cycloalkyl;
- R53 J S hydrogen, (C «
- R 54 and R 55 independently of the other are (C-
- R58 j S hydrogen, alkyl, alkanoyl, alkoxy, benzoyl, aryl or heteroaryl, where the last 3 radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R ⁇ 3 ;
- R 63 may be (C-
- D 3 , D 4 , D 5 and D 6 are independent of one another and are each a direct bond, oxygen, S(O)
- R56 R57 J R64 a nd R 65 independently of one another are each hydrogen, cyano, nitro, halogen, (Ci-CsJ-alkyl, (C ⁇ -Cs)- haloalkyl, (C2-C8)-alkenyl, (C2-C8)-haloalkenyl, (C2-C8)-alkynyl, (C2-C8)-haloalkynyl, (C-j-C8)-alkoxy-(C 1 -C4)-alkyl, (C-i-C ⁇ )- haloalkoxy-(C-
- R 66 independently of the others is hydrogen, (C ⁇ -C4)-alkyl, (C1-C4)- alkanoyl or (C3-C5)-cycloalkyl and
- R ⁇ 7 and R 68 independently of the other are each (C ⁇ -C4)-alkyl
- R6 9 independently of the others may be (C- ⁇ -C4)-alkyl, (C1-C4)- haloalkyl, (C-
- R l is hydrogen, (C ⁇ -C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C3-
- C8)-cycloalkyl or (C4-C8)-cycloalkenyl and where in the last 5 radicals one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O) x where x 0, 1 or 2,
- R may be aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D 4 R 57 or
- R 63 may be (C-
- ⁇ J5R64 I or the ring system formed by R u and R*, together with a further benzene ring or cyclohexane ring, forms a condensed ring system, preferably the indane, 1,2,3,4-tetrahydro- naphthalene, decalin or benzocycloheptane system, and the benzene ring in these condensed systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents D 6 R 65 , where in the compounds where the carbon atom between Y 4 and Z 2 where Y CH2 only carries the substituent W ⁇ R*, the substituents X and W ⁇ R* are cis to each other;
- D 3 , D 4 , D 5 and D 6 are independent of one another and are each a direct bond, oxygen, S(O)
- R66 independently of the others is hydrogen, (C-
- R56_ R57 R64 a nd R ⁇ 5 independently of one another are each hydrogen, cyano, nitro, halogen, preferably fluorine, (C-i-Cs)- alkyl, (C3-C8)-cycloalkyl, aryl, heterocyclyl, where in the last 3 radicals the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R 69 , where R 69 independently of the others may be (C-
- R 5 is hydrogen, halogen, CN, nitro, (C ⁇ -C4)-alkoxycarbonyl, (C1-C4)- alkylcarbamoyl, di-(C ⁇ -C4)-alkylcarbamoyl, (C-j-CsJ-alkoxy, (C-j-C ⁇ )- alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, aryl or (C3-C 8 )-cycloalkyl;
- W a is O, S or NR 71 ;
- W b is O or S
- each R 70 which may be the same or different from any other R 70 , is hydrogen, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted a ino, optionally substituted acyloxy, and may also form a 4 to 8 membered with R 6 , Rl I 2 or R1 I 3 , respectively with the Da, D " ! 2 or.
- each R 71 which may be the same or different from any other R 71 , is hydrogen, nitro, cyano, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted amino or optionally substituted acyloxy;
- R 72 and R 73 are alkyl or optionally substituted aryl;
- D 2 is e) a direct bond, NR 70 , N(O)R 70 , O, S, SO, SiR 2 R 73 , U'(CW)V, or f) U 1 '(PW , )V 1 , V 2, I U 2 '(SO 2 )U 3 ', Si(OR 72 )R 73 , Si(OR 72 )(OR 73 ),NR 70 O,
- W' is O, S or NR 7 ;
- W ' is O or S
- U 2 ' and U 3 ' independently of each other are a direct bond, NR 70 or O;
- R 1 ⁇ 2 is hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, in which up to CH2 units in a carbon containing group can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO2,
- NR 70 or SiR 72 R 73 can also be substituted by nitro, halogen, SF5 or D l 3 R ⁇ 13 and in which two adjacent D 12 Rl1 2 together with the carbons to which they are attached can form a condensed ring comprising 4 to 6 ring atoms which can be substituted one or more halogen or C-
- D l 3 has the same meaning as D l2 and R ⁇ ⁇ 3 has the same meaning as Rl 1 ; and in paragaraphs (13) - (16), aryl is as defined under (8) and, if it is not encompassed by the definition the carbon containing groups named under (13) to (16) can be substituted by one or more, preferably up to three (in the case of halogen up to the maximim number) of the same or different groups selected from halogen, cycloalkyl, phenoxy, substituted phenoxy, phenyl or substituted phenyl, with the proviso that at least one of the parameters defined in 13b, 15d or 16f or 16h applies.
- An inorganic anion is an anion of an inorganic acid, for example F-, CI-, Br-, I-, NO3-,
- An organic anion is an anion of an organic acid (carboxylic acid, sulfonic acid, phosphonic acid and the like) or an aromatic or heteroaromatic phenol-like compound.
- organic acid carboxylic acid, sulfonic acid, phosphonic acid and the like
- aromatic or heteroaromatic phenol-like compound include anions of mono- or bifunctional carboxylic acids and carboxylic acids such as acetic acid, propionic acid, maleic acid, succinic acid, glycolic acid, oxalic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid or lactic acid, and sulfonic acids such as p-toluenesulfonic acid, dodecylsulfonic acid or 1 ,5-naphthalenedisulfonic acid, or saccharin.
- a and D are part of a pyrimidine system, it is assumed that A is nitrogen and D is N + R. However, it cannot be excluded with absolute certainty that the radical R is in position 3 (i.e. that A is N + R and D is nitrogen).
- Z is (C3-C8)-cycloalkyl or (Cs-C ⁇ J-cycloalkenyl, it is preferably substituted by one or more, preferably up to 3, identical or different substituents selected from the group consisting of (C ⁇
- C ⁇ J-cycloalkyl C ⁇ -C4)-haloalkyl, preferably trifluoromethyl, halogen, (C1-C4)- dialkylamino, (C-
- (C ⁇ -C4)-alkylsilylmethoxy preferably dimethyl-(C ⁇ -C4)-alkylsilylmethoxy, (C3-C8)- cycloalkyl-(C-
- Preferred compounds of formula I are those in which
- R1 is hydrogen, halogen, (C-
- R 2 and R 3 are identical or different and are each hydrogen, (C-
- R 2 and R 3 together with the linking carbon atoms form an unsaturated 5- or 6- membered carbocyclic ring which, if it is a 5-membered ring, may contain an oxygen or sulfur atom in the place of a CH2 or which, or which may, if it is a
- 6-membered ring contain one or two nitrogen atoms instead of one or two CH units, and which may be substituted by 1, 2 or 3 identical or different radicals, these radicals being (C ⁇ -C4)-alkyl, preferably trifluoromethyl, halogen, (C-
- R 2 and R 3 together with the linking carbon atoms form a 5-, 6- or 7-membered alicyclic ring which may contain oxygen and/or sulfur in the place of one or two carbon ring members and which is, if desired, substituted by 1 , 2 or 3 (C-j-C4)-alkyl groups;
- A is CH and D is N + R or
- A is nitrogen and D is N + R;
- Q n_ is an anion such as Hal", NO3", BF4", BPh4" or PFQ ⁇ ;
- Rl is hydrogen, methyl, fluorine or chlorine
- R 2 and R 3 are each hydrogen, (C-
- R 2 and R 3 join with the linking carbon atoms to form an unsaturated 5- or 6- membered ring with or without substitution which may, in the case of the 5- membered ring, contain a sulfur atom instead of a CH2 unit; or
- R 2 and R 3 join with the linking carbon atoms to form a saturated 5- or 6-membered ring, which may contain a sulfur or oxygen atom instead of a CH2 unit;
- X is NH or oxygen.
- Y is a bond or a methylene group which is substituted by one or two, preferably by one, (C-
- R20 J S phenyl or substituted phenyl and the (C3-Cs)-cycloalkyl or (C5-C8)- cycloalkenyl radical may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of (C «
- 3)-hydrocarbon radicals mentioned may be replaced by hetero atom radicals such as O, NR ⁇ 0 " or
- Z (a) is a group of the formula II where X 1 is oxygen;
- Ry is (C 1 -C2 ⁇ )-alkyl, (C2-C2 ⁇ )-alkenyl, (C2-C2 ⁇ )-alkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals and where in the alkyl, alkenyl or alkynyl radicals mentioned one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by hetero atom units such as oxygen or SiR 27 R 28 , where R 27 and R 28 are each (C 1 -C4)-alkyl, preferably methyl, and where additionally 3 to 6 atoms of these hydrocarbon radicals, which may be modified as above, may form a cycle, and where these hydrocarbon radicals with or without the variations mentioned may be substituted by one or more, preferably by up to three (in the case of halogen up to the maximum number), identical
- R31 and R 32 independently of the other are each hydrogen or methyl; m 1 is 1 or 2; n 1 is 1 or 2;
- U is a direct bond, NR 38 or O; W is oxygen;
- V is a direct bond, NR 39 or oxygen; and R36 and R 37 are each (C ⁇ -C4)-alkyl or phenyl, preferably methyl;
- R 33 , R34_ R35 R38 a nd R 39 are identical or different and are each hydrogen, (C-
- R°. independently of the others is (C ⁇ -Cs)-alkyl where one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by oxygen and which, with or without the variations mentioned, may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D R 43 , or
- R 0 may be aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D 2 R 44 ;
- D " ! and D 2 are independent of one another and are each a direct bond, -O-,
- R46 independently of the others is hydrogen, (C-
- R43 and R44 independently of the other are each hydrogen, halogen, preferably fluorine, (C-
- Y 4 is a direct bond or CH2
- Z 2 is oxygen
- R u is hydrogen, (C ⁇ -C4)-alkyl, trifluoromethyl or (C ⁇ -C4)-alkoxy;
- R 52 is hydrogen, (C-
- R* is as defined above under (12 c).
- Rl is hydrogen
- R 2 and R 3 are each hydrogen, methyl, ethyl, propyl, methoxy, (C2-C3)-alkenyl, amino, (C ⁇ -C4)-alkylamino, (C-
- R 2 and R 3 together with the ring system to which they are attached form the quinazoline or quinoline system, which may be fluorine-substituted in the carbocyclic moiety;
- R 2 and R 3 together with the carbon atoms to which they are attached form a saturated 6-membered ring, which may contain an oxygen or sulfur atom instead of a CH2 group;
- Especially preferred compounds are those compounds where R1 is hydrogen;
- R 2 is methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, (C-
- R 3 is fluorine, chlorine, bromine, cyano, vinyl, ethynyl, (C-
- R 2 and R 3 form, together with the ring system to which they are attached, the quinazoline system, which may be substituted by one fluorine atom.
- X is NH
- Z is (a) cyclopentyl or cyclohexyl, where both radicals may be substituted as above under (10) and where, in the case of cyclohexyl, 1 ,4-substitution is preferred, the substituents being cis to one another; or
- R z is hydrogen
- Y 1 is CH 2 ;
- Y 2 is CH 2 ;
- Y 4 is a direct bond or CH2
- Z 2 is oxygen
- R u is hydrogen or methyl
- Z (a) is cyclohexyl which is preferably substituted by a radical selected from the group consisting of
- 3)-alkyloximino where this substituent is in position 4 of the cyclohexyl ring and cis with respect to the -(X-Y)- unit and where, if not included in the definitions above, one or more, preferably up to three, CH2 groups in the (C-i-C ⁇ )-, (C2-C8)-hydrocarbon radicals mentioned may be replaced by hetero atom radicals, such as O, or SiR " !
- R ⁇ ⁇ " and R ⁇ 2 " have the meanings of R 1 1 , R l 2 , and where additionally 3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle, and where these hydrocarbon radicals with or without the variations may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of hydroxyl, halogen, alkyl, haloalkyl, cycloalkyl, acyl, phenyl, substituted phenyl; heteroaryl may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents; aryl is as defined under (8);
- R 24 and R 25 are identical or different and independently of one another are each hydrogen, (C-
- X 1 is oxygen; R z is hydrogen;
- Ry is (C- -Ci5)-alkyl, aryl or heterocyclyl meaning a heteroaromatic ring system, where the aryl or heterocyclyl radical may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals and where in the alkyl radical mentioned one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by oxygen, and where additionally 3 to 8 atoms of this alkyl radical, which may be modified as above, may form a cycle, and where this alkyl radical with or without the variations mentioned may be substituted by one or more halogen atoms (in the case of fluorine up to the maximum number of identical or different substituents), and where the substituents X and Ry on the heteroaliphatic six-membered ring are preferably cis to one another; or (c) is a group of the formula (III)
- nl 1 or 2
- R°. independently of the others is (C ⁇ -Cs)-alkyl where one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by oxygen, and which with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D 1 R 43 , or
- R°. may be aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number), identical or different radicals D 2 R 44 ; or (d) is a group of the formula IV where
- R u is hydrogen
- R* is (C ⁇ -C8)-alkyl in which one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by oxygen, and which with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D 3 R 5 6 or
- R* may be aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D R 57 .
- R 1 is hydrogen
- R 2 is ethyl or methoxymethyl
- R 3 is chlorine, bromine or methoxy, preferably those for which R 2 is ethyl and R 3 is chlorine; Other preferred compounds are those where
- R4 and R 5 which may be the same or different, are hydrogen, halogen, nitro, cyano, a negative charge, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heterocyclyl or optionally substituted cycloalkyl.
- R is hydrogen, halogen, nitro, cyano, a negative charge, optionally substituted C-
- C2 _ C20" a, kynyl, and R 5 is hydrogen, halogen, nitro, cyano, optionally substituted C-
- R 4 is hydrogen, halogen, C-
- -C4-alkyl or a negative charge if R 5 COR 5 ', and
- R 4 is hydrogen
- R 5 is hydrogen or methyl
- D a is a direct bond, NR 70 , O, S, SO, SO2 or U a (CW a )V a , and especially a direct bond, NR 70 , O, S, O(CO), NR 70 (CO), (CO) or (CNR 7 ""), preferably a direct bond, S, NR 70 (CO),O(CO) or (CO).
- R 3 is hydrogen, cyano, C-
- R 1 4 is C-j-C4-alkyl, C ⁇ -C4-haloalkyl, C-
- -C4-haloalkoxy; or R 113 is a negative charge when D 13 (CO)O, (SO2)O, U1"(PW1")V1"O, which replaces Q n ";
- each R 70 which may be the same or different from any other R 70 , is hydrogen, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted amino, optionally substituted acyloxy, and optionally and may also form a 4 to 8 membered with R 6 , R 1 12 or R l 13 , respectively with the Da, D 12 or.
- each R 71 which may be the same or different from any other R 7 ⁇ , is hydrogen, nitro, cyano, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted amino or optionally substituted acyloxy;
- R 72 and R 73 are alkyl or optionally substituted aryl; and especially
- R 6 is cyano, C-
- D 12 is a direct bond, NR 70 , N(O)R 70 , O, S, SO, SiR 72 R 73 , U'fCWJV, U 1 '(PWT)V V 2 ', U 2 '(SO 2 )U 3 ', Si(OR 72 )R 73 , Si(OR 72 )(OR 73 ),NR 0 O,
- U',U 1 ' V, V 1 ' and V 2 ' independently of each other are a direct bond, NR 70 , S or O,
- W is O, S or NR 71 ;
- W 1 ' is O or S; U 2 ' and U 3 ', independently of each other are a direct bond, NR 70 or O; and D 12 ' is N(O)R 70 , SiOR 72 R 73 , SiOR 72 OR 73 , U'(CNR 7 )V', S(CW')V, U'(CW')S,
- D 12 ' is O(CO)NH, NR 70 (CO)NH, O(CS)NH, NR 0 (CS)NH, (CO)NH, (CS)NH, O(CO), NR 70 (CO), SO 2 NH in which R 1 12 is hydrogen;
- U' and U 1 ' independently of each other, are a direct bond, NR 70 , S or O
- W is O, S or NR 71
- W 1 ' is O or S
- V, V 1 ' and V 2 ' independently of each other, are a direct bond, NR 70 , S or O'
- U 2 ' and U 3 ' independently of each other, are NR 70 or O
- R 12 j s hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, in which up to CH2 units in a carbon containing group can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO2, NR 70 or
- SiR 72 R 73 can also be substituted by nitro, halogen, SF5 or
- D13R113 and in which two adjacent D1 2 /D 12 'R 1 12 together with the carbons to which they are attached can form a condensed ring comprising 4 to 6 ring atoms which can be substituted one or more halogen or C «
- D l 3 has the same meaning as D 12 and R 1 13 has the same meaning as Rl 2 ;
- R112 j s hydrogen, cyano, C-
- U and U 1 " independently of each other, are a direct bond, NR 70 , S or O, W" is O, S or NR'
- V V 1 " and V 2 ", independently of each other, are a direct bond, NR 70 , S or O,
- U 2 " and U 3 " independently of each other, are a direct bond, NR 70 or O;
- R l 13 is hydrogen, cyano, C-
- R® is C-
- D 2 ' is O(CO)NH, NR 70 ,(CO)NH, O(CS)NH, NR 0 (CS)NH, (CO)NH, (CS)NH, O(CO), NR 70 (CO) or SO2NH, in which case R 2 is hydrogen,
- U' and U1' independently of each other, are a direct bond, NR 70 , S or O,
- W is O, S or NR 70 ,
- V, V 1 ' and V 2 ' independently of each other, are a direct bond, NR 70 , S or O,
- R6 is aryl or heteroaryl, in which these groups and their named variations can also be substituted by up to three and, in the case of halogen up the maximum number, of the same or different nitro, halogen, SF5 or D l 2 R " ! l 2 > and these groups and their named variations should also be substituted by one or more of the same or different D ⁇ 2 R 1 1 2 , in which
- D 12 is a direct bond, O, U'(CW')V, U (PW 1 , )V V 2 ', U 2 '(SO 2 )U 3 ', in which
- U' and U1' independently of each other, are a direct bond or O, W is O or S ,
- V, V " 1' and V 2 ' independently of each other, are a direct bond, NR 70 , S or O,
- U 2 ' and U 3 ' independently of each other are a direct bond or O, or
- D 12 ' is U'(CW')S, U (PW 1 ')Vl'v 2 ', U 2 '(SO 2 )U 3 ', or
- D l2 ' is COO or SO2O, in which R ⁇ ⁇ 2 is a negative charged or hydrogen, or
- D 12 ' is O(CO)NH, NR 70 (CO)NH, O(CS)NH, NR 0 (CS)NH, (CO)NH, (CS)NH, O(CO), NR 0 (CO) or SO2NH in which case R 1 2 is hydrogen,;
- W 1 ' is O or S
- V 1 ' or V 2 ' independently of each other, are a direct bond, NR 70 , S or O,
- U 3 ' is R 70 or O.
- radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and the corresponding unsaturated and/or substituted radicals can in each case be straight-chain or branched in the carbon skeleton.
- alkyl radicals are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyl radicals, hexyl radicals, such as n-hexyl, i-hexyl and 1 ,3-dimethylbutyl, heptyl radicals, such as n-heptyl, 1-methylhexyl and 1 ,4-dimethylpentyl; alkenyl and alkynyl radicals have the meanings of the unsaturated radicals which are possible and which correspond to the alkyl radicals; alkenyl is, for example, allyl, 1-methyl
- Cycloalkyl is a carbocyclic saturated ring system preferably having 3 - 8 carbon atoms, for example cyclopropyl, cyclopentyl or cyclohexyl, but also bicyclic systems, for example the norbornyl group, the bicyclo[2.2.2]octane radical and tricyclic systems, for example adamantyl.
- Halogen is, for example, fluorine, chlorine, bromine or iodine.
- Haloalkyl, haloalkenyl and haloalkynyl are alkyl, alkenyl and alkynyl, respectively, which are partially or fully substituted by halogen, preferably by fluorine, chlorine and/or bromine, in particular by fluorine or chlorine, for example monohaloalkyl, perhaloalkyl, CF3, CHF2, CH2F,
- haloalkoxy is, for example, OCF3,
- a hydrocarbon radical is a straight-chain, branched or cyclic and saturated or unsaturated aliphatic or aromatic hydrocarbon radical, for example alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or aryl; preferably, a hydrocarbon radical is alkyl, alkenyl or alkynyl having up to 12 carbon atoms or cycloalkyl having 3, 4, 5, 6 or 7 ring atoms or phenyl; the same applies analogously to a hydrocarbon radical in a hydro- carbonoxy radical.
- aryl is a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl.
- a heterocyclic radical or ring can be saturated, unsaturated or heteroaromatic; it preferably contains one or more hetero units in the ring, i.e. hetero atoms or ring members, including substituted hetero atoms, preferably selected from the group consisting of N, O, S, SO, SO2; it is preferably an aliphatic heterocyclyl radical having 3 to 7 ring atoms or a heteroaromatic radical having 5 or 6 ring atoms and it contains 1 , 2 or 3 hetero units.
- Substituents which are suitable for a substituted heterocyclic radical are the substituents mentioned further below, and additionally oxo.
- the oxo group can also be present on the hetero ring atoms, which can exist at various oxidation levels, for example in the case of N and S.
- Substituted radicals such as substituted hydrocarbon radicals, for example substituted alkyl, alkenyl, alkynyl, aryl, phenyl and benzyl, or substituted heterocyclyl or heteroaryl, are, for example, a substituted radical derived from the unsubstituted skeleton, the substituents being, for example, one or more, preferably 1, 2 or 3, radicals selected from the group consisting of halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxy, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino, such as acylamino, mono- and dialkylamino, and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkyl- s
- radicals having carbon atoms include as substituents, in addition to the saturated hydrocarbon-containing radicals mentioned, corresponding unsaturated aliphatic and aromatic radicals, such as alkenyl, alkynyl, alkenyloxy, alkynyloxy, phenyl, phenoxy, etc., with or without substitution.
- Preferred among the radicals having carbon atoms are those having 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms.
- Preferred substituents are generally selected from the group consisting of halogen, for example fluorine and chlorine, (C ⁇ -C4)-alkyl, preferably methyl or ethyl, (C ⁇ j -C4)-haloalkyl, preferably trifluoromethyl, (C-
- halogen for example fluorine and chlorine
- C ⁇ j -C4)-haloalkyl preferably trifluoromethyl
- substituents methyl, methoxy and chlorine.
- Mono- or disubstituted amino is a chemically stable radical selected from the group consisting of the substituted amino radicals which are N-substituted, for example by one or two identical or different radicals selected from the group consisting of alkyl, alkoxy, acyl and aryl; preferably monoalkylamino, dialkylamino, acylamino, arylamino, N-alkyl-N-arylamino and N-heterocycles; preference is given to alkyl radicals having 1 to 4 carbon atoms; aryl is preferably phenyl or substituted phenyl; acyl is defined as indicated further below and is preferably (C ⁇ -C4)-alkanoyl. The same applies analogously to substituted hydroxylamino or hydrazino.
- Unsubstituted or substituted phenyl is preferably phenyl which is unsubstituted or mono- or polysubstituted, preferably up to trisubstituted, by identical or different radicals selected from the group consisting of halogen, (C-
- (C ⁇ -C4)-haloalkyl, (C ⁇ -C4)-haloalkoxy and nitro for example o-, m- and p-tolyl, dimethylphenyl radicals, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluoro- and -trichlorophenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.
- An acyl radical is the radical of an organic acid, for example the radical of a carboxylic acid and radicals of acids derived therefrom, such as thiocarboxylic acid, iminocarboxylic acids with or without N-substitution, or the radical of carbonic monoesters, carbamic acid with or without N-substitution, sulfonic acids, sulfinic acids, phosphonic acids, phosphinic acids.
- Acyl is, for example, formyl, alkylcarbonyl such as [(C-j-C4)alkyl]carbonyl, phenylcarbonyl, alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl and other radicals of organic acids.
- alkylcarbonyl such as [(C-j-C4)alkyl]carbonyl
- phenylcarbonyl alkyloxycarbonyl
- phenyloxycarbonyl benzyloxycarbonyl
- alkylsulfonyl alkylsulfinyl
- N-alkyl-1-iminoalkyl N-alkyl-1-iminoalkyl and other radicals of organic acids.
- radicals may be substituted even further in the alkyl or phenyl moiety, for example in the alkyl moiety by one or more radicals selected from the group consisting of halogen, alkoxy, phenyl and phenoxy; examples of substituents in the phenyl moiety are the substituents already mentioned further above in general for substituted phenyl.
- -C8)-alkylsilylethynyr denotes, for example, the trimethylsilylethynyl or the tert-butyldimethylsilylethynyl group
- (C ⁇ -C4)-hydroxyalkyl denotes, for example, the hydroxymethyl
- -C4)-haloalkyl denote (C«
- -C4)-alkyr denotes, for example, methylthiomethyl, ethylthiomethyl, propylthiomethyl, 2-methylthioethyl, 2-ethylthioethyl or
- arylthio denotes, for example, the phenylthio or the 1- or 2-naphthylthio group
- aryloxy denotes, for example, the phenoxy- or 1- or 2-naphthyloxy group
- heterocyclyloxy or “heterocyclylthio” denotes one of the abovementioned heterocyclic radicals which are linked via an oxygen or sulfur atom
- cycloalkoxy or "cycloalkylthio” denotes one of the abovementioned cycloalkyl radicals which are linked via an oxygen or sulfur atom
- aroyl denotes, for example, the benzoyl, naphthoyl or the biphenylcarbonyl group
- aryl-(C ⁇ -C4)-alkanoyl denotes, for example, the phenylacetyl
- -C4)-alkoxycarbonyl denotes, for example, the thienylmethoxycarbonyl, furylmethoxycarbonyl, tetrahydrofurylmethoxycarbonyl or the pyridylethoxycarbonyl group
- aryloxycarbonyl denotes, for example, the phenoxycarbonyl, naphthoxycarbonyl or the biphenyloxycarbonyl group
- heterocyclyloxycarbonyl denotes, for example, the tetrahydropyran-4- oxycarbonyl group
- -C2o)-alkanoyloxy denotes, for example, the formyloxy, acetoxy
- R 26 is hydrogen, (C-
- the compounds of the formula I have one or more asymmetric carbon atoms or stereoisomers at double bonds. Enantiomers or diastereomers may therefore be present.
- the invention embraces both the pure isomers and mixtures thereof. Mixtures of diastereomers can be separated into the components by conventional methods, for example by selective crystallization from suitable solvents or by chromatography. Racemates can be separated into the enantiomers by conventional methods, for example by salt formation with an optically active acid, separation of the diastereomeric salts and liberation of the pure enantiomers using a base.
- the invention furthermore relates to a process for preparing compounds of the formula I which comprises reacting a compound of the formula (V)
- R is as defined under formula I and L is a leaving group, for example halogen, alkylthio, alkanesulfonyloxy or arylsulfonyloxy, alkylsulfonyl or arylsulfonyl, preferably halogen, if appropriate with the addition of salts such as, for example, AgBF4, AgNO3 or Nal, replacing, if appropriate, the anion of the compounds obtained in this manner by other anions, similarly to known methods [for example Liebigs Ann. Chem. 1978, 1937; Methoden der Org. Chemie/Houben-Weyl (D. Klamann, Ed.), 4th Edition, Vol. E16a, Part 2, p. 1008 ff., Thieme, Stuttgart 1990].
- salts such as, for example, AgBF4, AgNO3 or Nal
- the abovementioned reaction is carried out in a temperature range from 20 to 150"C, if appropriate in an inert organic solvent such as acetonitrile, acetone, 2-butanone, N.N-dimethylforrnamide, N.N-dimethylacetamide, dimethyl sulfoxide, N- methylpyrrolidin-2-one, dioxane, tetrahydrofuran, 4-methyl-2-pentanone, methanol, ethanol, butanol, ethylene glycol, ethylene glycol dimethyl ether, toluene, chlorobenzene or xylene. It is also possible to use mixtures of the solvents mentioned.
- an inert organic solvent such as acetonitrile, acetone, 2-butanone, N.N-dimethylforrnamide, N.N-dimethylacetamide, dimethyl sulfoxide, N- methylpyrrolidin-2-one, dioxane, tetrahydr
- the active substances are suitable for controlling animal pests, especially insects, arachnids, helminths and molluscs, and very particularly preferably for controlling insects and arachnids, which are encountered in agriculture, in animal breeding, in forestry, in the protection of stored products and materials, and in the hygiene sector. They are active against normally sensitive and resistant species and against all or certain stages of development.
- the abovementioned pests include:
- Acarina for example, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp.,
- Rhipicephalus spp. Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,
- Chorioptes spp. Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp. and Eutetranychus spp..
- Symphyla for example, Scutigerella immaculata.
- Thysanura for example, Lepisma saccharina.
- Orthoptera for example, Blatta orientalis, Periplaneta americana, Leucophaea madeirae, Blatella germanica, Acheta domesticus,
- Gryllotalpa spp. Locusta migratoria migratorioides, Melanoplus differentialis and
- heteroptera From the order of the heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.
- From the order of the Homoptera for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis spp., Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arandinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelus bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.
- Drosophila melanogaster Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hypobosca spp., Stomoxys spp., Oestrus spp., Hyporma spp., Tabanus spp., Tannia spp., Bibio hortulanus,
- Oscinella frit Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and
- helminths for example, Haemonchus, Trichostrongulus
- the plant-parasitic nematodes which can be controlled in accordance with the invention include, for example, the root-parasitic soil nematodes such as, for example, those of the genera Meloidogyne (root-knot nematodes, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica), heterodera and Globodera (cyst-forming nematodes, such as Globodera rostochiensis, Globodera pallida, heterodera trifolii) and of the genera Radopholus (such as Radopholus similis), Pratylenchus (such as Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus),
- the root-parasitic soil nematodes such as, for example, those of the genera Meloidogyne (root-knot nematodes, such as
- Tylenchulus such as Tylenchulus semipenetrans
- Tylenchorhynchus such as Tylenchorhynchus dubius and Tylenchorhynchus claytoni
- Rotylenchus such as Rotylenchus robustus
- Helicotylenchus such as Helicotylenchus multicinctus
- Belonoaimus such as Belonoaimus longicaudatus
- Longidorus such as Longidorus elongatus
- Trichodorus such as Trichodorus primitivus
- Xiphinema such as Xiphinema index
- the compounds according to the invention can also be used to control the nematode genera Ditylenchus (stem parasites, such as Ditylenchus dipsaci and Ditylenchus destructor), Aphelenchoides (leaf nematodes, such as Aphelenchoides ritzemabosi) and Anguina (leaf-gall nematodes, such as Anguina tritici).
- Ditylenchus stem parasites, such as Ditylenchus dipsaci and Ditylenchus destructor
- Aphelenchoides leaf nematodes, such as Aphelenchoides ritzemabosi
- Anguina leaf-gall nematodes, such as Anguina tritici
- the invention also relates to compositions, especially insecticidal and acaricidal compositions, which comprise the compounds of the formula I in addition to suitable formulation auxiliaries.
- compositions according to the invention comprise the active substances of the formulae I in general in a proportion of from 1 to 95% by weight. They can be formulated in various ways depending on the biological and/or chemicophysical parameters which prevail. Possible formulations which are suitable are therefore:
- WP wettable powders
- EC emulsifiable concentrates
- SL aqueous solutions
- SC oil- or water-based dispersions
- SE suspoemulsions
- SE dusts
- WG water-dispersible granules
- ULV formulations, microcapsules, waxes or baits.
- the formulation auxiliaries required are likewise known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell N.J.; H.v. Olphen, "Introduction to Clay Colloid Chemistry", 2nd ed., J. Wiley & Sons, N.Y.; Marsden, “Solvents Guide”, 2nd ed., Interscience, N.Y. 1950; McCutcheon's, "Detergents and Emulsifiers Annual", MC Publ.
- Wettable powders are preparations, uniformly dispersible in water, which contain, beside the active substance and in addition to a diluent or inert material, wetting agents, for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, alkyl- or alkylphenolsulfonates, and dispersing agents, for example sodium ligninsulfonate or sodium 2,2'-dinaphthylmethane-6,6 , -disulfonate.
- wetting agents for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, alkyl- or alkylphenolsulfonates
- dispersing agents for example sodium ligninsulfonate or sodium 2,2'-dinaphthylmethane-6,6 , -disulfonate.
- Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons, with addition of one or more emulsifiers.
- organic solvent for example butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons.
- emulsifiers the following can be used, for example: calcium salts of alkylaryl- sulfonates, such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.
- alkylaryl- sulfonates such as Ca dodecylbenzenesulfonate
- nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan
- Dusts are obtained by grinding the active substance with finely divided solid substances, for example talc, natural clays such as kaolin, bentonite, pyrophillite or diatomaceous earth.
- Granules can be prepared either by atomizing the active substance onto adso ⁇ tive, granulated inert material or by applying active substance concentrates onto the surface of carrier materials such as sand or kaolinites, or of granulated inert material, by means of adhesives, for example polyvinyl alcohol or sodium polyacrylate, or alternatively mineral oils.
- Suitable active substances can also be granulated in the fashion conventional for the preparation of fertiliser granules, if desired as a mixture with fertilisers.
- the concentration of active substance is, for example, from approximately 10 to 90% by weight, the remainder to 100% by weight being composed of customary formulation components. In the case of emulsifiable concentrates, the concentration of active substance may be from approximately 5 to 80% by weight. Dust formulations comprise in most cases from 5 to 20% by weight of active substance, sprayable solutions from about 2 to 20% by weight. In the case of granules, the content of active substance depends partly on whether the active compound is in liquid or solid form and on which granulation auxiliaries, fillers, etc. are being used.
- the abovementioned formulations of active substance comprise, if appropriate, the adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers which are customary in each case.
- the concentrates which are in the commercially customary form, are if appropriate diluted in the customary manner for their use, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and some microgranules. Dust and granule preparations, and also sprayable solutions, are normally not diluted any further with other inert substances before being used.
- the application rate required varies with the external conditions, such as temperature and humidity among others. It can fluctuate within wide limits, for example between 0.0005 and 10.0 kg/ha or more of active substance, but is preferably between 0.001 and 5 kg/ha.
- the active substances according to the invention may be present in their commercially customary formulations, and in the application forms prepared from these formulations, as mixtures with other active substances, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth regulators or herbicides.
- the active substance content of the use forms prepared from the commercially customary formulations can be from 0.00000001 to 95% by weight of active substance, preferably between 0.00001 and 1% by weight.
- the active substances according to the invention are also suitable for controlling ecto- and endoparasites in the veterinary medicine sector or in the sector of animal husbandry.
- the active substances according to the invention are in this case applied in a known fashion, such as by oral application in the form of, for example, tablets, capsules, potions or granules, by dermal application in the form of, for example, dipping, spraying, pouring-on and spotting-on and powdering, and also by parenteral application in the form of, for example, injection.
- novel compounds, according to the invention, of the formula I can accordingly also be employed particularly advantageously in livestock husbandry (for example cattle, sheep, pigs and poultry such as chickens, geese etc.).
- livestock husbandry for example cattle, sheep, pigs and poultry such as chickens, geese etc.
- the novel compounds if appropriate in suitable formulations (cf. above) and if appropriate with the drinking water or feed, are administered orally to the animals. Since they are excreted in active form in the droppings, the development of insects in the animal droppings can be prevented very simply in this fashion.
- the dosages and formulations suitable in each case are particularly dependent on the type and stage of development of the productive animals and also on the degree of infestation, and can easily be determined and fixed by conventional methods.
- the novel compounds can be employed, for example, in dosages of 0.01 to 1 mg/kg of body weight.
- Some compounds of the formula I according to the invention are also distinguished by an fungicidal action.
- Fungal pathogens which have already penetrated the plant tissue can be successfully subjected to curative control. This is particularly important and advantageous in the case of those fungal diseases which can no longer be controlled effectively with the otherwise customary fungicides when infection has taken place already.
- the spectrum of action of the claimed compounds embraces various economically important phytopathogenic fungi, for example Plasmopara viticola, Phytophthora infestans, Erysiphe graminis, Piricularia oryzae, Pyrenophora teres, Leptosphaeria nodorum, Pellicularia sasakii and Puccinia recondita.
- the compounds according to the invention are also suitable for use in technical fields, for example as wood preservatives, as preservatives in paints, in cooling lubricants for metalworking, or as preservatives in drilling and cutting oils.
- the active substances according to the invention in their commercially customary formulations can be employed either alone or in combination with other fungicides known from the literature.
- the abovementioned components for combinations are known active substances of which many are described in The Pesticide Manual, edited by C D S Tomlin, 11th edition (1997), bublished by the British Crop Protection Council.
- the active substance content of the use forms prepared from commercially customary formulations can vary within wide limits, and the concentration of active substance in the use forms can be from 0.0001 up to 95% by weight of active substance, preferably between 0.0001 and 1 % by weight.
- the formulations are applied in a customary manner adapted to suit the use forms.
- a dust is obtained by mixing 10 parts by weight of active substance and 90 parts by weight of talc as inert material and comminuting in a hammer mill.
- a wettable powder which is easily dispersible in water is obtained by mixing 25 parts by weight of active substance, 65 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurinate as wetting and dispersing agent, and grinding in a pinned disk mill.
- a dispersion concentrate which is easily dispersible in water is prepared by mixing 40 parts by weight of active substance with 7 parts by weight of a sulfosuccinic monoester, 2 parts by weight of a sodium ligninsulfonate and 51 parts by weight of water and grinding in a ball mill to a fineness of below 5 microns.
- An emulsifiable concentrate can be prepared from 15 parts by weight of active substance, 75 parts by weight of cyclohexane as solvent and 10 parts by weight of ethoxylated nonylphenol (10 EO) as emulsifier.
- Granules can be prepared from 2 to 15 parts by weight of active substance and an inert granule carrier material such as attapulgite, granulated pumice and/or quartz sand. It is advantageous to use a suspension of the wettable powder of Example b) with a solids content of 30% which is sprayed onto the surface of attapulgite granules which are then dried and intimately mixed.
- the proportion by weight of the wettable powder in this case is about 5% and that of the inert carrier material is about 95% of the finished granules.
- a Petri dish whose bottom is covered with filter paper and which contains about 5 ml of culture medium is prepared.
- Pieces of filter paper with about 30, 24-hour-old eggs of the tobacco budworm (Heliothis virescens) are dipped into an aqueous solution of the formulated preparation to be examined for about 5 seconds and subsequently placed into the Petri dish.
- a further 200 ⁇ l of the aqueous solution are spread over the culture medium.
- the Petri dish is sealed and then kept at about 25°C in a controlled climate chamber. After 6 days storage, the effect of the preparation on the eggs and the larvae which may have hatched from these is determined.
- At a concentration of 300 ppm (based on the content of active compound), compounds 132,191,199 and 439 caused a mortality of 90-100%.
- Germinated field bean seeds (Vicia fabae) with radicles are transferred into brown bottles filled with tap water and subsequently populated with approximately 100 black bean aphids (Aphis fabae). Plants and aphids are then dipped for 5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution has run off, plants and animals are stored in a controlled climate chamber (16 hours of light/day, 25"C, 40 - 60% relative atmospheric humidity). After 3 and 6 days storage, the effect of the preparation on the aphids is determined. At a concentration of 300 ppm (based on the content of active compound), compounds 132,191 and199 caused an aphid mortality of 90-100%.
- the leaves of 12 rice plants having a stem length of 8 cm are dipped for 5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution has run off, the rice plants treated in this manner are placed in a Petri dish and populated with about 20 larvae (L3 stage) of the rice leafhopper species Nilaparvata lugens. The Petri dish is sealed and then stored in a controlled climate chamber (16 hours of light/day, 25"C, 40 - 60% relative atmospheric humidity). After 6 days storage, the mortality among the leafhopper larvae is determined. At a concentration of 300 ppm (based on the content of active compound), compounds 132,191,199 and 439 caused a mortality of 90-100%.
- Cut stems of bean plants (Phaseolus vulga ⁇ s) carrying one leaf are transferred into brown bottles filled with tap water and subsequently populated with approximately 100 spider mites (Tetranychus urticae). Plant leaf and spider mites are then dipped for
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Abstract
Compounds of formula (I), in which A is CH and D is N+R; or A is nitrogen and D is N+R; or A is N+R and D is nitrogen, where R is CR?4R5DaR6, Qn-¿ is an inorganic or organic anion, n being 1, 2, 3 or 4; X, Y, Z, and R?1, R2 and R3¿ have various meanings as defined in the claims, are useful pesticidal, especially insecticidal activity.
Description
SUBSTITUTED NITROGEN HETEROCYCLES AND THEIR USE AS
PESTICIDES
The invention relates to novel substituted pyridines and pyrimidines and condensed systems derived therefrom, processes for their preparation and their use as pesticides, especially insecticides and acaricides.
It is already known that certain 4-amino- and 4-alkoxy-heterocycles have fungicidal, acaricidal and insecticidal activity (for example WO-A-93/19 050, DE-A-43 43 250, WO-A-95/07 890, WO-A-94/21 613). However, the biological activity of these compounds, in particular at low application rates and concentrations, is not satisfactory in all use examples.
Novel, positively charged heterocycles of the formula I have been found
/γ-z
X
in which the radicals and groups are as defined below, which, while showing good tolerance by plants and favourable toxicity in respect of warm-blooded animals, are highly suitable for controlling insects and acarids.
The invention therefore relates to compounds of the formula I in which
(1) A is CH and D is N+R or
A is nitrogen and D is N+R or
A is N+R and D is nitrogen, where
R is CR R5DaR6,
(2) Qn" is an inorganic or organic anion, n being 1 , 2, 3 or 4;
(3) R1 is hydrogen, halogen, (C-i-Csr-alkyl, (Cπ-C8)-haloalkyl, (Cπ-C8)-alkoxy or
(C3-C6)-cycloalkyl;
(4) R2 and R3 are identical or different and are each hydrogen, (Ci-Csr-alkyl,
(C2-C8)-alkenyl, (C2-C8)-alkynyl, (C-j-CβJ-alkoxy, halogen, hydroxy, cyano, nitro, thiocyanato, (C-i-Cβr-alkoxycarbonyl, (Cπ-C8)-alkylthio,
(C-|-C8)-alkylsulfinyl, (C-j-CsJ-alkylsulfonyl, amino; (C-i-Cβr-alkylamino,
(C-j-CβJ-dialkylamino or (C3-C6)-cycloalkyl, and in which in the alkyl, cycloalkyl, alkenyl, alkynyl groups or the groups derived from them, such as alkoxy, alkylfyl, alkanoyl, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino, a saturated carbon unit can be replaced by a hetero atom unit such as oxygen, S(O)x, where x = 0, 1 or 2 or by dimethylsilyl and further in these groups or derived groups up to 3 hydrogen atoms can be replaced by halogen and in the case of fluorine also all hydrogen atoms can be replaced by fluorine; or
R2 and R3 together with the carbon atoms to which they are attached form an unsaturated 5- or 6-membered carbocyclic ring which may, if it is a 5-membered ring, contain an oxygen or sulfur atom instead of CH2, or which may, if it is a 6-membered ring, contain one or two nitrogen atoms instead of one or two CH units, and which may be substituted by 1, 2 or 3 identical or different radicals, these radicals being (C-J-C4)- alkyl, (Cη-C4)-haloalkyl, preferably trifluoromethyl, halogen, (C1-C4)- alkoxy or (Cι-C4)-haloalkoxy; or
R2 and R3 together with the carbon atoms to which they are attached form a saturated 5-, 6- or 7-membered carbocyclic ring which may contain oxygen and/or sulfur instead of one or two CH2 groups and which may be substituted by 1, 2 or 3 (C-|-C4)-alkyl groups;
(5) X is O, S(O)q where q = 0, 1 or 2, NR7, NR CO, NR7CS or CR8R9, where R7 is hydrogen and R8 and R9 independently of one another are each hydrogen or (Cπ_C4)-alkyl,
(6) Y - Z together are a (C1-C2θ)-hydrocarDθn radical which is straight-chain or branched and in which one or more, preferably up to three, CH2 may be replaced by hetero atom radicals such as O, NR10, S, SO, SO2 or
SiR1 1R12, where R10 is hydrogen, (Cπ-C4)-alkyl or (C-|-C4)-acyl, and
R11 and R12 are identical or different and are each independently of the other (C-|-C4)-alkyl, phenyl or substituted phenyl, and where this (Cπ-C2θ)-hydrocarbon radical with the possible abovementioned variations may be substituted by one or more, preferably up to three, identical or different radicals selected from the group consisting of (C-i-CyJ-alkyl,
(C2-C4)-alkenyl,
(C2-C4)-alkynyl,
(C3-C7)-cycloalkyl,
(C3-C7)-cycloalkenyl, halogen, halo-(Cπ-C4)-alkyl, halo-(C-|-C4)-alkoxy, hydroxy and
(Cπ-C4)-acyl; or, if not included in the above definitions,
(7) Y is a bond or a bivalent hydrocarbon chain having 1 to 6 carbon atoms which may be substituted by one or more, preferably up to three, identical or different radicals selected from the group consisting of
(C^CyJ-alkyl,
(C2-C4)-alkenyl,
(C3-C7)-alkynyl,
(C3-C7)-cycloalkyl,
(8) Z is aryl or O-aryl, where aryl is preferably a naphthyl or phenyl group, heterocycyl or heterocyclyloxy, each of which may be substituted by one or more, preferably up to five, in particular up to three, identical or different radicals selected from the group consisting of halogen, (C3-C8)-cycloalkyl,
(C3-C8)-cycloalkenyl , phenoxy, substituted phenoxy, phenylthio, substituted phenylthio, phenyl, substituted phenyl, optionally substituted heterocyclyl, optionally substituted heterocyclylthio
NO2,
-C(O)-R13, acetoxy, hydroxyl, cyano,
SiRl R15R16,
O-SiR14R15R16,
NR17R18
S(O)R19, SO2R19,
(C2-Ci2)-alkenyl, (Cι-Ci2)-a'koxy and (Ci-C-^r-alkyltt-i0; and
R13 is (C-|-C7)-alkyl, halo-(C-|-C7)-alkyl, (C3-C7)-cycloalkyl, halo-
(C-C7)-cycloalkyl, (Cι-C7)-alkoxy, phenyl or substituted phenyl;
R14, Rη5 and Rη6 are identical or different and are each independently of one another (C-|-C4)-alkyl, phenyl and/or substituted phenyl;
R17 and R18 are identical or different and are each independently of the other hydrogen, (Cπ-C4)-alkyl and/or (C<|-C4)-acyl;
R19 is (Cπ-Cιo)-a'kyl, phenyl or substituted phenyl; wherein (C-|-C-|2)-alkyl, (Ci-C^J-alkoxy, (Cη-C-^r-alkylthio and (C2-Cπ2)-alkenyl one or more, preferably up to 3, CH2 groups may be replaced by hetero atom radicals such as O, S, SO, SO2, R10' or SiRU'Rl2'; R10'_ R11" and R12' have the meanings of R10, R1 1 , R12; the (Ci-C^J-alkyl radical with or without the abovementioned variations may also be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group below consisting of halogen, halo-(Cι-C4)-alkoxy, hydroxyl, (C3-C8)- cycloalkyl, (C3-C8)-cycloalkenyl, (Cι-C4)-acyl, phenoxy, substituted phenoxy, phenyl, substituted phenyl, phenylthio and substituted phenylthio; in the (C-|-C7)-alkoxy and (C1-C7)- alkylthio radicals, one or more, preferably up to three, CH2 groups may be replaced by O, and these radicals may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of halogen, phenyl, substituted phenyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkenyl, phenoxy and substituted phenoxy; or, if not included in the above definitions,
(9) Y is a bond or a bivalent hydrocarbon chain having 1 to 6 carbon atoms, preferably methylene, which is substituted by one or more, preferably
up to three, identical or different radicals selected from the group consisting of
(C-i-CyJ-alkyl.
(C2-C4)-alkenyl,
(C3-C7)-alkynyl,
(C3-C7)-cycloalkyl,
(C3-C7)-cycloalkenyl, halogen, halo-(C-j-C4)-alkyl, halo-(Cι-C4)-alkoxy, hydroxyl and (Cπ-C4)-acyl; and
(10) Z is (C3-C8)-cycloalkyl or (C5-C8)-cycloalkenyl, where a CH2 group of the carbocycle may be replaced by NR2^;
R20 js phenyl or substituted phenyl and the (C3-C8)-cycloalkyl or (C5- CβJ-cycloalkenyl radical may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of (Cι-C 8)-alkyl,
(C3-C8)-cycloalkyl,
(C3-C8)-cycloalkoxy,
(C2-C18)-alkenyl,
(C2-C18)-alkynyl,
(C-|-C-|2)-alkoxy,
(Cι-C-|2)-alkanoyloxy, formyl, (C2-C12)-acyl,
(C-|-C-|2)-alkoxycarbonyl,
SiR2l R22R23,
NR24R 5,
C(O)NR24R25,
hydroxyl, halogen, aryl, heteroaryl,
O aryl,
O heteroaryl,
CH2θaryl,
CH2θheteroaryl,
(Cπ-Ci8)-alkanediyldioxy,
(Cη-C 3)-alkoximino and
(C2-C-|8.-alkylidene and where, if not included in the above definitions, one or more, preferably up to three, CH2 groups in the (Cι_C-|8h (C2-C-18)-. (C-|.C-|2)"> (C2-C-|2r- and (C-|-C-|3)-hydrocarbon radicals mentioned may be replaced by hetero atom radicals such as O, NRπ0" or SiRη ι"Rl 2", these hetero atom radicals preferably not being adjacent to one another, where R10", R1 1" and R12" have the meanings of R10,
R11, R12 and where additionally 3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle and where these hydrocarbon radicals with or without these variations may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of hydroxyl, halogen, alkyl, haloalkyl, cycloalkyl, acyl, phenyl, substituted phenyl, optionally substituted heterocyclyl, phenylthio and substituted phenylthio; where heteroaryl may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents; where aryl is as defined under (8); where R24 and R ^ are identical or different and are each independently of the other hydrogen, (C-|-C4)-alkyl, (Cπ-C4)-acyl, (C3-
Ce)-cycloalkyl, phenyl and substituted phenyl and where R21, R22,
R23 are identical or different and are each independently of the others
(Cι-Ci8)-alkyl, (C-|-C-|8)-alkoxy, (C3-C8)-cycloalkyl and aryl, where in the (Cι-Ci8)-hydrocarbon radicals more than one, preferably up to three, non-adjacent CH2 groups may be replaced by oxygen and where
3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle, it also being possible for two of the carbon radicals (for example R21 and
R22) attached to silicon together to form a cycle, the silicon atom in this case being a ring atom of this cycle, and where additionally these (Cι-C-|8)-hydrocarbon radicals with or without the variations may be substituted by one or more (in the case of halogen up to the maximum number) identical or different radicals selected from the group consisting of halogen, haloalkyl, cycloalkyl, where the substituents on the cycloalkyl or cycloalkenyl radicals defined under (10) may be cis or trans with respect to the unit (X-Y) and where, in the case that the cycloalkyl group is the cyclohexyl radical and the abovementioned units are in the 1 ,4 position, preference is given to the cis configuration; or
(11) Y is a bond; and
(12) Z is (a) a group of the formula II
where each X"1 independently of the other is sulfur or oxygen; Rz is hydrogen, (Cπ-C4)-alkyl, trifluoromethyl or (C-|-C4)-alkoxy; or
Ry is alkyl, alkenyl, alkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals and where in the alkyl, alkenyl or alkynyl radicals mentioned one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O)x, where x = 0, 1 or 2, NR26 or SiR27R28, where R26 is hydrogen, (Cη-C4)-alkyl, (Cπ-C4)-alkoxy or
(Cπ-C4)-alkanoyl and R27 and R28 are each (C-|-C4)-alkyl, preferably methyl; and where additionally 3 to 12 atoms of these hydrocarbon radicals, which may be modified as mentioned above, may form a cycle and where these hydrocarbon radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals selected from the group consisting of halogen, aryl, aryloxy, arylthio, cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, alkanoyl, cycloalkanoyl, haloalkanoyl, aroyl, arylalkanoyl, cycloalkylalkanoyl, heterocyclylalkanoyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, cycloalkyl- alkoxycarbonyl, arylalkoxycarbonyl, heterocyclylalkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, alkanoyloxy, haloalkanoyloxy, cycloalkanoyloxy, cycloalkylalkanoyloxy, aroyloxy, arylalkanoyloxy, heterocycloylalkanoyloxy, alkylsulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyanato or nitro, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or where R and Rz together form a three- to eight-membered ring system which is spirocyclically linked to the ring system containing the hetero atoms χ1 and where one or two CH2 groups, preferably one CH2 group, may be replaced by hetero atom units such as oxygen, S(O)n where n = 0, 1 or 2 or NR29, where R29 is hydrogen, alkyl, alkoxy, alkanoyl, benzoyl, aryl or heteroaryl, where the benzoyl, aryl or heteroaryl radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, and where the ring system formed by Ry and Rz may be unsubstituted or substituted by up to three, but preferably one, substituents and where these substituents are identical or different and are each alkyl, haloalkyl, alkoxy,
alkylthio, aryl, aryloxy, arylthio, aralkyl, arylalkoxy, arylalkylthio, cycloalkyl, cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, trialkylsilyl or alkoxycarbonyl, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or where the ring system formed by Ry and Rz, together with a further benzene ring or cyclohexane ring, forms a condensed ring system, preferably the indane, 1,2,3,4-tetrahydronaphthalene, decalin or benzocycloheptane system, and where the benzene ring in these condensed systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents; in particular those groups of the formula II where
Ry is (C-|-C2θ)-alkyl, (C2-C2θ)-a'kenyl, (C2-C2o)"alkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals and where in the alkyl, alkenyl or alkynyl radicals mentioned one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O)x, where x = 0, 1 or
2, NR26 or SiR27R28 where R26 is hydrogen, (Cπ-C4)-alkyl,
(C-j-C4)-alkoxy or (C<|-C4)-alkanoyl and R27 and R28 are each
(Cη-C4)-alkyl, preferably methyl, and where additionally 3 to 12 atoms of these hydrocarbon radicals, which may be modified as above, may form a cycle and where these hydrocarbon radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of halogen, aryl, aryloxy, arylthio, (C3-C8)- cycloalkoxy, (C3-C8)-cycloalkylthio, heterocyclyl,
heterocyclyloxy, heterocyclylthio,
(C3-C8)- cycloalkanoyl, (C2-Cπ2)-haloalkanoyl, aroyl, aryl-(Cπ-C4)- alkanoyl, (C3-C8r-cycloalkyl-(C-|-C4)-alkanoyl, heterocyclyl-(Cη-
C4)-alkanoyl, (C-|-C-j2)-alkoxycarbonyl, (C-1-C12)- haloalkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C3-C8)- cycloalkyl-(Cπ-C4)-alkoxycarbonyl, aryl-(C-j-C4)-alkoxycarbonyl, heterocyclyl-(C-|-C4)-alkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, (Cπ-C<i2r-alkanoyloxy, (C2-C12)- haloalkanoylalkoxy, (C3-C8)-cycloalkanoyloxy, (C3-C8)- cycloalkyl-(Cι-C4)-alkanoyloxy, aroyloxy, aryl-(C-|-C4)-alkanoyl- oxy, heterocyclyl-(C-|-C4)-alkanoyloxy, (Cι-Ci2.-alkyl- sulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyanato or nitro, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or where Ry and Rz together form a three- to eight-membered ring system, which is spirocyclically linked to the ring system containing the hetero atoms χ1 and where one or two CH2 groups, preferably one CH2 group, may be replaced by hetero atom units such as oxygen, S(O)n where n = 0, 1 or 2 or NR29, where R29 is hydrogen, (C-|-C8)-alkyl, (C-|-C8)-alkoxy, (C-i-Cβ)- alkanoyl, benzoyl, aryl or heteroaryl, where the benzoyl, aryl or heteroaryl radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents and where the ring system formed by Ry and Rz may be unsubstituted or substituted by up to three, but preferably one, substituents and where these substituents are identical or different and are each (C-i-Cs)- alkyl, (C-j-CβJ- aloalkyl, (Cη-CβJ-alkoxy, (C-j-CsJ-alkylthio, (C3-
C8)-cycloalkyl, (C3-C8)-cycloalkoxy, (C3-C8)-cycloalkylthio, aryl,
aryloxy, arylthio, aryl-(Cπ-C4)-alkyl, aryl-(C-|-C4)-alkoxy, aryl-
(C-j-C4)-alkylthio, heterocycyl, heterocyclyloxy, heterocyclylthio,
(C-)-C8)-trialkylsilyl, preferably (C-|-C8)-alkyldimethylsilyl, or
(Cπ-C8)-alkoxycarbonyl, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or where the ring system formed by Ry and Rz, together with a further benzene ring or cyclohexane ring, forms a condensed ring system, preferably the indane, 1,2,3,4-tetrahydro- naphthalene, decahydronaphthalene or benzocycloheptane system and where the benzene ring in these condensed systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, where among the compounds where the carbon atom between the hetero atoms X^ carries only the substituent Ry, the substituents X and Ry are preferably cis to each other;
Rz is hydrogen, (C-|-C4)-alkyl, trifluoromethyl or (C-|-C4)-alkoxy; or
(b) a group of formula
Yπ, Y2 and Y3 independently of one another are each a group of the formula -O-, -CO-, -CNR30-, -S(O)r where r = 0, 1 or 2,
-N(O)|R30- where I = 0 or 1 or a group of the formula CR31R32; or
γ1 or Y3 stands in place of a direct bond, where
R30 JS hydrogen, (C-|-C4)-alkyl, (C-|-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkynyl, (Cπ- C4)-alkoxy, (Cπ-C4)-haloalkoxy,
(Cπ-C4)-halo- alkylthio, (Cη-C^-alkanoyl, (C2-C4)-haloalkanoyl, (C3-C5)- cycloalkyl, (Cπ-C4)-alkylsulfonyl, (C<|-C4)-haloalkylsulfonyl, (Cπ -C4)-alkoxy-(C-| -C4)-alkyl, (C-| -C4)-alkoxycarbonyl;
R31 and R32 independently of the other are each hydrogen, hydroxyl, halogen, cyano, (C-|-C4)-alkyl, (Cι-C4)-haloalkyl, (C2-C4)- alkenyl, (C2-C4)-haloalkenyl, (C2-C4)-alkynyl, (C2-C4)- haloalkenyl, (C3-C5)-cycloalkyl, (C-|-C4)-alkanoyl, (C-1-C4)- haloalkanoyl,
(Cπ-C4)-haloalkoxy, (C1-C4)- alkylthio or (Cπ-C4)-haloalkylthio; m1 is 0, 1, 2, 3 or 4, preferably 1 or 2; n1 is 0, 1 , 2, 3 or 4, preferably 1 or 2; Z1 is a direct bond, NR33, O, S(O)s where s = 0, 1 or 2, OSO2,
SO2O, NR3 SO2, SO2NR35, SiR36R37 or
U-C(W)-V, where R36 and R37 are eaC (Cη-C4)-alkyl or phenyl, preferably methyl;
U is a direct bond, NR38 or O;
W is oxygen or sulfur, preferably oxygen;
V is a direct bond, NR39 or oxygen, where R33 R34 R35 R38 and R39 are identical or different and are each hydrogen, alkyl, alkoxy, alkanoyl or cycloalkyl;
R°. are substituents which are independent of one another and each is halogen, cyano, nitro, (Cι-C2θ)-alkyl, (C2-C2o)-alkenyl,
(C2-C2o)-3lkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, where in the last 5 radicals one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by a
carbonyl group or by hetero atom units such as oxygen, S(O)x where x = 0, 1 or 2, NR40 or SiR41R42 and where these last 5 radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D1R43, or
R°. is aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D2R44, or two adjacent radicals zl-R0- may combine with the carbon atoms to which they are attached to form a fused cycle having 4 to 6 ring atoms which is carbocyclic or contains hetero ring atoms selected from the group consisting of O, S and N and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C-|-C4)-alkyl and oxo, or
R33, R3^ or R39 independently of one another may combine with the
R°. located at Z to form a 4- to 8-membered ring system in which one or two CH2 groups, preferably one CH2 group, may be replaced by hetero atom units such as oxygen, S(O)tι where t =
0, 1 or 2 or NR45, where
R40 is hydrogen, (Cπ-C4)-alkyl, (C-|-C4)-alkoxy or (C-|-C4)-alkanoyl;
R41 and R42 independently of the other are each (C<|-C4)-alkyl, preferably methyl; D1 and D2 are independent of each other and each is a direct bond, oxygen, S(O)k, SO2O, OSO2, CO, OCO, COO, NR46,
SO2NR46, NR46SO2, ONR46, NR 6O, NR 6CO, CONR46 or
SiR47R48, and k = 0, 1 or 2, where R46 independently of the others is hydrogen, (Cπ-C4)-alkyl, (C1-C4)- alkanoyl or (C3-C5)-cycloalkyl;
R47 and R48 independently of the other are each (C-|-C4)-alkyl;
R43 and R44 independently of the other are each hydrogen, cyano, nitro, halogen, (C<|-C8)-alkyl, (Cπ-C8)-haloalkyl, (C2-C8)- alkenyl, (C2-C8)-haloalkenyl, (C2-C8)-alkynyl, (C2-C8)- haloalkynyl, (C1-C8)-alkoxy-(C-|-C4)-alkyl, (C-|-C8)-haloalkoxy- (Cι-C4)-alkyl. (C<\-Cs)-a\ky o-(C C4)-a\\<s/\, (Cη-Cβ)- haloalkylthio-(C-|-C4)-alkyl, (C3-C8)-cycloalkyl, (C4-C8)- cycloalkenyl, (C3-C8)-cycloalkyl-(Cπ-C4)-alkyl, (C4-C8)- cycloalkenyl-(C-|-C4)-alkyl, aryl, heterocyclyl, aryl-(C-|-C4)-alkyl or heterocyclyl-(C-|-C4)-alkyl, where in the last 8 radicals the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R49, or R43 and R44 located at the same carbon atom together are an oxo group, where
R49 is (Cι-C )-alkyl, (C1-C4)-haloalkyl, (C-|-C4)-alkoxy, (C-|-C )- haloalkoxy, cyano, nitro or halogen;
R45 is hydrogen, (C-j-CsJ-alkyl, (Cπ-C4)-haloalkyl, (C-|-C4)-alkoxy,
(Cπ-C4)-alkylthio, (C3-C5)-cycloalkyl, (C2-C4)-alkenyl, (C2-C4)- alkynyl, (Cπ-C4)-alkanoyl, (C2-C4)-haloalkanoyl, (C2-C4)- alkoxyalkyl, phenyl-(C-|-C4)-alkyl or phenyl where the phenyl groups may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R^O, where
R50 is (Cι-C4)-alkyl, (Cπ-C4)-haloalkyl, (C-i^-alkoxy, (C-j^)- alkylthio, halogen or cyano; or, if not included in the above definitions,
Y4 is a direct bond or CH2;
Z2 is oxygen, NR51 , S(O)m where m = 0, 1 or 2;
RU and wl-Rt are substituents of the heteroaliphatic ring system, where
Ru is hydrogen, halogen, cyano, (C<|-C4)-aIkyl, (C-|-C4)-haloalkyl,
(C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C2-C4)-alkynyl, (C2-C4)- haloalkynyl, (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C-1-C4)- alkoxy, (C-|-C4)-haloalkoxy, (C-i^J-alkanoyloxy, (C-1-C4)- haloalkanoyloxy, (C-|-C4)-alkylthio or (C-|-C4)-haloalkylthio;
W is a direct bond, oxygen, -NR52-, -CO-, -COO-, CONR52-, sulfur, -C=N-, -C=N-O- or -NR52O-;
R* is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, where in the last 5 radicals one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O)x where x = 0, 1 or 2, NR53 or SiR5 R55, and where these last 5 radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D3R56, or
R* may be aryl or heterocyclyl, where both of these radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D4R57 or
Ru and R* together form a three- to eight-membered ring system which is spirocyclically linked to the ring system containing the hetero atoms Y4 and Z2 and in which one or two CH2 groups,
preferably one CH2 group, may be replaced by hetero atom units such as oxygen, S(O)n where n = 0, 1 or 2, or NR58, where
R51 js hydrogen, (Cf-C^alkyl, (C-|-C4)-haloalkyl, (C2-C4)-alkenyl,
(C2-C4)-haloalkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkynyl, (Cπ-
C4)-alkoxy, (Cπ-C4)-alkanoyl, (C2-C4)-haloalkanoyl, (C1-C4)- alkoxy- (Cπ-C4)-alkyl, (Cπ-C4)-alkylthio-(C-|-C4)-alkyl, (C1-C4)- alkoxycarbonyl, (C-|-C4)-alkylsulfonyl,
phenylcarbonyl, phenyl-(Cπ-C4)-alkyl or phenyl, where the last 3 radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R59, or
R51 is CONR60R61 where
R6° and R6<l independently of the other are each hydrogen, (C-1-C4)- alkyl or phenyl, where the phenyl group may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R^2, and R62 and R59 independently of the other are each (C1-C4)-alkyl, (C-|-
C4)-haloalkyl, (C-|-C4)-alkoxy, (Cι-C4)-haloalkoxy, (C-1-C4)- alkylthio or halogen; R52 JS hydrogen, (Cη-C4)-alkyl, (C-j-O^-alkanoyl or (C3-C5)-cycloalkyl; R53 JS hydrogen, (C«|-C4)-alkyl, (C-|-C4)-alkoxy or (Cπ-C4)-alkanoyl;
R54 and R55 independently of the other are (C-|-C4)-alkyl, preferably methyl;
R58 jS hydrogen, alkyl, alkanoyl, alkoxy, benzoyl, aryl or heteroaryl, where the last 3 radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R^3;
R63 may be (C-|-C4)-alkyl, (Cπ-C4.-haloalkyl, (Cπ-C4)-alkoxy, (C-1-C4)- haloalkoxy, cyano, nitro or halogen, and the ring system formed by Ru and R* may be unsubstituted or substituted by up to
three, but preferably one, substituents D5R64, or the ring system formed by Ru and R , together with a further benzene ring or cyclohexane ring, forms a condensed ring system, preferably the indane, 1,2,3,4-tetrahydronaphthalene, decalin or benzocycloheptane system, and the benzene ring in these condensed systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents D6R65, where
D3, D4, D5 and D6 are independent of one another and are each a direct bond, oxygen, S(O)|<, SO2O, OSO2, CO, OCO, COO,
SO2NR66, NR66SO2, NR66O, ONR66, NR66, NR66CO, CONR66 or SiR67R68, where k = 0, 1 or 2; and R56( R57J R64 and R65 independently of one another are each hydrogen, cyano, nitro, halogen, (Ci-CsJ-alkyl, (Cη-Cs)- haloalkyl, (C2-C8)-alkenyl, (C2-C8)-haloalkenyl, (C2-C8)-alkynyl, (C2-C8)-haloalkynyl, (C-j-C8)-alkoxy-(C1-C4)-alkyl, (C-i-Cβ)- haloalkoxy-(C-|-C4)-alkyl, (C1-C8)-alkylthio-(C1-C4)-alkyl, (C<|-C8)-haloalkylthio-(C-|-C4)-alkyl, (C3-C8)-cycloalkyl, (C4- C8)-cycloalkenyl, (C3-C8)-cycloalkyl-(C-|-C4)-alkyl, (C4-C8)- cycloalkenyl-(C-|-C4)-alkyl, aryl, heterocyclyl, aryl-(C1-C4)-alkyl or heterocyclyl-(Cι-C4)-alkyl, where in the last 8 radicals the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R69, where
R66 independently of the others is hydrogen, (Cπ-C4)-alkyl, (C1-C4)- alkanoyl or (C3-C5)-cycloalkyl and
R^7 and R68 independently of the other are each (Cπ-C4)-alkyl, and
R69 independently of the others may be (C-ι-C4)-alkyl, (C1-C4)- haloalkyl, (C-|-C4)-alkoxy, (C-|-C4)-haloalkoxy, cyano, nitro, halogen, (C-|-C4)-alkanoyl or (C2-C4)-haloalkanoyl, or two of the radicals
R56, R57, R64, R65, R69 which are located at the same carbon atom together, and in each case independently of the others, are an oxo group; in particular those groups of the formula IV where
Rl is hydrogen, (Cι-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C3-
C8)-cycloalkyl or (C4-C8)-cycloalkenyl and where in the last 5 radicals one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O)x where x = 0, 1 or 2,
NR53 or SiR54R55, and where these last 5 radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D3R56 0r
R may be aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D4R57 or
Ru and R* together form a five- or six-membered ring system which is linked, preferably spirocyclically, to the ring system containing the hetero atoms Y4 and Z2, and in which one CH2 group may be replaced by hetero atom units such as oxygen, S(O)n where n = 0, 1 or 2 or NR58, where R53 JS hydrogen, (Cι-C4)-alkyl, (Cπ-C4)-alkoxy or (Cπ-C4)-alkanoyl and R54 and R55 independently of the other are (Cι-C4)-alkyl, preferably methyl;
R58 JS hydrogen, (C-|-C8)-alkyl, (C-|-C8)-alkanoyl, benzoyl, aryl or heteroaryl, where the last 3 radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R^3, and
R63 may be (C-|-C4)-alkyl, (Cπ-C4)-haloalkyl, (Cπ-C4)-alkoxy,
(C-|-C4)-haloalkoxy, cyano, nitro or halogen, and the ring
system formed by Ru and R* may be unsubstituted or substituted by up to three, but preferably one, substituents
ΓJ5R64I or the ring system formed by Ru and R*, together with a further benzene ring or cyclohexane ring, forms a condensed ring system, preferably the indane, 1,2,3,4-tetrahydro- naphthalene, decalin or benzocycloheptane system, and the benzene ring in these condensed systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents D6R65, where in the compounds where the carbon atom between Y4 and Z2 where Y = CH2 only carries the substituent W^R*, the substituents X and W^R* are cis to each other;
D3, D4, D5 and D6 are independent of one another and are each a direct bond, oxygen, S(O)|<, SO2O, OSO2, CO, OCO, COO,
SO2NR66, NR66SO2, NR66O, ONR66, NR66, NR66CO or
CONR66, and k = 0, 1 or 2, R66 independently of the others is hydrogen, (C-|-C4)-alkyl, (C1-C4)- alkanoyl or (C3-C5)-cycloalkyl and
R56_ R57 R64 and R^5 independently of one another are each hydrogen, cyano, nitro, halogen, preferably fluorine, (C-i-Cs)- alkyl, (C3-C8)-cycloalkyl, aryl, heterocyclyl, where in the last 3 radicals the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R69, where R69 independently of the others may be (C-|-C4)-alkyl, (C1-C4)- haloalkyl, (Cπ-C4)-alkoxy, (C-j-C4)-haloalkoxy, cyano, nitro, halogen, or two of the radicals R56_ R57 R64 R65 R69 which are located at the same carbon atom, together and in each case independently of the others, are an oxo group;
(13) R4 is a) hydrogen, halogen or optionally substituted alkyl or
(b) a negative charge, which can represent Qn"
(14) R5 is hydrogen, halogen, CN, nitro, (Cπ-C4)-alkoxycarbonyl, (C1-C4)- alkylcarbamoyl, di-(Cη-C4)-alkylcarbamoyl, (C-j-CsJ-alkoxy, (C-j-Cβ)- alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, aryl or (C3-C8)-cycloalkyl;
(15) Da is c) a direct bond, NR70, N(O)R70, O, S, SO, SO2, C(=Wa), OC(=Wa) or d) Ua(C=Wa)Va (Ua and Va are a direct bond, NR70, S or O, except Va is not a bond when Ua is bond or O), SiR72R73, Ub(P=Wb)V Vc, Ub(SO2)Uc (one of Ub and Uc is a direct bond, NR70, S or O and the other is NR70), Ua(CWa)(CWa)Vb, NR70O, O NR70, NR70 NR70,
N=N, -N=, - NR70-N= or -O-N= , and
Wa is O, S or NR71;
Wb is O or S;
Ua, Vb and Vc, independently of each other are a direct bond, NR70, S or O each R70, which may be the same or different from any other R70, is hydrogen, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted a ino, optionally substituted acyloxy, and may also form a 4 to 8 membered with R6, Rl I 2 or R1 I 3, respectively with the Da, D"!2 or. Dπ 3 to which they are attached, and in the case Da is UbP(=Wb)VbVc, the two R6 groups together with the VbPVc, to which they are attached can form a 4 to 8 membered ring
each R71 , which may be the same or different from any other R71 , is hydrogen, nitro, cyano, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted amino or optionally substituted acyloxy;
R72 and R73 are alkyl or optionally substituted aryl;
(16) R6 is hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, in which up to three CH2 units in a carbon containing group can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO2, NR70 or Si R72R73 and can also be substituted by nitro, halogen, SF5 or D12R1 12 and in the case Da is UbP(=Wb)V Vc, the two R6 groups together with the V PVc, to which they are attached can form a 4 to 8 membered ring
D 2 is e) a direct bond, NR70, N(O)R70, O, S, SO, SiR 2R73, U'(CW)V, or f) U1'(PW ,)V1 ,V2, I U2'(SO2)U3', Si(OR72)R73, Si(OR72)(OR73),NR70O,
ONR70, NR70NR70, N=N, =N-, =N-NR70- =N-O-, -N=, -NR70-N= or - O-N= and
U',1)1' V, V1' and V2', independently of each other are a direct bond,
NR70, S or O
W' is O, S or NR7 ;
W ' is O or S;
U2' and U3', independently of each other are a direct bond, NR70 or O;
(g) R1 π2 is hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, in which up to CH2 units in a carbon containing group can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO2,
NR70 or SiR72R73 and can also be substituted by nitro, halogen, SF5 or Dl 3Rπ 13 and in which two adjacent D12Rl12 together with the carbons to which they are attached can form a condensed ring comprising 4 to 6 ring atoms which can be substituted one or more halogen or C-|-C4-alkyl; or
(h) R112 is a negative charge for D12 = (CO)O, (SO2)O, U1'(PW')V1'θ which replaces the ion Qn-; or R 12 is hydrogen for D12 = O(CO)NH, NR 0(CO)NH, O(CS)NH, NR70(CS)NH, (CO)NH, (CS)NH, O(CO), NR70(CO), SO2NH;
Dl 3 has the same meaning as Dl2 and Rπ π 3 has the same meaning as Rl 1 ;
and in paragaraphs (13) - (16), aryl is as defined under (8) and, if it is not encompassed by the definition the carbon containing groups named under (13) to (16) can be substituted by one or more, preferably up to three (in the case of halogen up to the maximim number) of the same or different groups selected from halogen, cycloalkyl, phenoxy, substituted phenoxy, phenyl or substituted phenyl, with the proviso that at least one of the parameters defined in 13b, 15d or 16f or 16h applies.
An inorganic anion is an anion of an inorganic acid, for example F-, CI-, Br-, I-, NO3-,
SO42-, HSO4-, PO43-, HPO42-, H2PO4-, PO33- or N3-, or a complex anion, for example BF4-, PFβ- or tetraphenylborate.
An organic anion is an anion of an organic acid (carboxylic acid, sulfonic acid, phosphonic acid and the like) or an aromatic or heteroaromatic phenol-like compound. These are, for example, anions of mono- or bifunctional carboxylic acids and carboxylic acids such as acetic acid, propionic acid, maleic acid, succinic acid, glycolic acid, oxalic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid or lactic acid, and sulfonic acids such as p-toluenesulfonic acid, dodecylsulfonic acid or 1 ,5-naphthalenedisulfonic acid, or saccharin.
If A and D are part of a pyrimidine system, it is assumed that A is nitrogen and D is N+R. However, it cannot be excluded with absolute certainty that the radical R is in position 3 (i.e. that A is N+R and D is nitrogen).
If Z is (C3-C8)-cycloalkyl or (Cs-CβJ-cycloalkenyl, it is preferably substituted by one or more, preferably up to 3, identical or different substituents selected from the group consisting of (C<|-Ci2)-alkyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkyl-(C-|-C4)-alkyl, (C-|-
C8)-alkoxy, (C3-C8)-cycloalkoxy, (C-|-C4)-alkoxy-(C1-C4)-alkyl, (C3-C8.-cycloalkyl-
(C1-C4)-alkoxy, tri-(C-|-C8)-alkylsilyl, preferably dimethyl-(Cπ-C8)-alkylsilyl or triethylsilyl, di-(C-|-C8)-alkyl-(C3-C8)-cycloalkylsilyl, preferably dimethylcyclohexylsilyl, di-(C-|-C8)-alkyl-(phenyl-(Cπ-C4)-alkyl)-silyl, preferably dimethyl(phenyl-(C-|-C4)- alkyl)silyl, di-(Cπ-C8)-alkyl-(Cι-C4)-haloalkylsilyl, preferably dimethyl-(C-|-C4)- haloalkylsilyl, dimethylphenylsilyl), (C-j-Cs. -haloalkyl, halogen, (C-j-C4)-haloalkoxy,
heteroaryl, phenyl, phenyl-(Cι-C4)-alkyl, benzyloxy, benzyloxy-(C-|-C4)-alkyl, benzylthio, phenylthio and phenoxy, where heteroaryl or phenyl in the last eight radicals may be unsubstituted or substituted by one or two substituents, these substituents being identical or different and being in each case (C<|-C8)-alkyl, (C3-
CβJ-cycloalkyl (Cι-C4)-haloalkyl, preferably trifluoromethyl, halogen, (C1-C4)- dialkylamino, (C-|-C4)-alkylthio, (C-j-Csr-alkoxy, (Cπ-C4)-haloalkoxy, (Cη-C4)-alkoxy-
(C1-C4)-alkoxy, H5C2-O-[CH2-CH2-O-]x, 2-(tetrahydro-2H-pyran-2-yloxy)ethoxy,
(C2-C8)-alkenyl, (C2-C8)-alkynyl, benzyloxy, which may carry one or two identical or different substituents selected from the group consisting of (C«|-C4)-alkyl, (C-1-C4)- haloalkyl, (Cπ-C4)-alkoxy, (Cπ-C4)-haloalkoxy and halogen in the phenyl moiety, tri-
(Cι-C4)-alkylsilylmethoxy, preferably dimethyl-(Cι-C4)-alkylsilylmethoxy, (C3-C8)- cycloalkyl-(C-|-C4)-alkoxy, 1,3-dioxolan-2-ylmethoxy, tetrahydrofuran-2-ylmethoxy and tetrahydro-2H-pyran-2-ylmethoxy.
Preferred compounds of formula I are those in which
R1 is hydrogen, halogen, (C-|-C4)-alkyl, (Cπ-C4)-haloalkyl or (C3-C5)-cycloalkyl;
R2 and R3 are identical or different and are each hydrogen, (C-|-C4)-alkyl, (C1-C4)- haloalkyl, (C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C2-C4)-alkynyl, (C2-C4)- haloalkynyl, trimethylsilylalkynyl, (Cη-C4)-alkoxy, (C<|-C4)-haloalkoxy, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C-|-C4)-haloalkoxy-(C-|-C4)-alkyl, (C1-C4)- alkoxy-(C-|-C4)-haloalkyl, (C-|-C4)-haloalkoxy-(Cπ-C4)-haloalkyl, halogen, hydroxy, (C-|-C4)-hydroxyalkyl, (Cπ-C4)-alkanoyl, (C<|-C4)-haloalkanoyl, (C3-C5)-cycloalkyl, (C3-C5)-halocycloalkyl, cyano, (C-|-C4)-cyanoalkyl, nitro, (C-|-C4)-nitroalkyl, thiocyanato, (C-|-C4)-thiocyanatoalkyl, (C1-C4)- alkoxycarbonyl, (C-|-C4)-alkoxycarbonyl-(C-|-C4)-alkyl, (C1-C4)- haloalkoxycarbonyl, (Cπ-C4)-alkylthio, (C-|-C4)-alkylthio-(C-|-C4)-alkyl, (Cπ- C4)-haloalkylthio, (Cπ-C4)-alkylsulfinyl, (Cι-C4)-haloalkylsulfinyl, (C1-C4)- alkylsulfonyl (Cι-C4)-haloalkylsulfonyl; amino, (C-ι-C4)-alkylamino or C-j- C4)-dialkylamino
R2 and R3 together with the linking carbon atoms form an unsaturated 5- or 6- membered carbocyclic ring which, if it is a 5-membered ring, may contain an
oxygen or sulfur atom in the place of a CH2 or which, or which may, if it is a
6-membered ring, contain one or two nitrogen atoms instead of one or two CH units, and which may be substituted by 1, 2 or 3 identical or different radicals, these radicals being (Cπ-C4)-alkyl,
preferably trifluoromethyl, halogen, (C-|-C4)-alkoxy or (Cπ-C4)-haloalkoxy; or
R2 and R3 together with the linking carbon atoms form a 5-, 6- or 7-membered alicyclic ring which may contain oxygen and/or sulfur in the place of one or two carbon ring members and which is, if desired, substituted by 1 , 2 or 3 (C-j-C4)-alkyl groups;
Preferred compounds of formula I also are those in which
A is CH and D is N+R or
A is nitrogen and D is N+R;
Qn_ is an anion such as Hal", NO3", BF4", BPh4" or PFQ~;
It is also preferred that
Rl is hydrogen, methyl, fluorine or chlorine;
R2 and R3 are each hydrogen, (C-|-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, amino, (Cι-C4)-alkylamino, (C-ι-C4)-dialkylamino, trimethylilylethynyl, methoxycarbonyl, (C-|-C4)-haloalkyl, (C2-C4)-haloalkenyl, methoxy, ethoxy, halogen, methoxymethyl or cyano; or
R2 and R3 join with the linking carbon atoms to form an unsaturated 5- or 6- membered ring with or without substitution which may, in the case of the 5- membered ring, contain a sulfur atom instead of a CH2 unit; or
R2 and R3 join with the linking carbon atoms to form a saturated 5- or 6-membered ring, which may contain a sulfur or oxygen atom instead of a CH2 unit;
X is NH or oxygen.
Other preferred compounds are those I in which
Y is a bond or a methylene group which is substituted by one or two, preferably by one, (C-|-C4)-alkyl radical; and
Z is (C3-C8)-cycloalkyl or (Cs-CsJ-cycloalkenyl, where a CH2 group of the carbocycle may be replaced by NR20;
R20 JS phenyl or substituted phenyl and the (C3-Cs)-cycloalkyl or (C5-C8)- cycloalkenyl radical may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of (C«|-C18)-alkyl,
(C3-C8)-cycloalkyl,
(C3-C8)-cycloalkoxy,
(C2-C18)-alkenyl,
(C2-C18)-alkynyl,
(Cπ-Ci2)-alkoxy,
SiR21R22R23, NR24R25,
CONR2 R25, hydroxy, halogen, aryl, heteroaryl,
O aryl,
O heteroaryl,
CH2θaryl,
CH2θheteroaryl,
(C-|-C-|8)-alkanediyldioxy,
(C-|-C-|3)-alkyloximino and
(C2-C-|8)-alkylidene and where, if not included in the above definitions, one or more, preferably up to three, CH2 groups in the (C«|-Cπ8)-. (C2-C18)-, (C1-C12)-. (C2-C12)- and (Cι-C-|3)-hydrocarbon radicals
mentioned may be replaced by hetero atom radicals such as O, NRπ 0" or
SiR1 '' "RI 2 ", these hetero atom radicals preferably not being adjacent to one another, where R10", R1 1" and R12" have the meanings of R10, R1 1, R12 and where additionally 3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle and where these hydrocarbon radicals with or without these variations may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of hydroxyl, halogen, alkyl, haloalkyl, cycloalkyl, acyl, phenyl, substituted phenyl, phenylthio and substituted phenylthio; where heteroaryl is unsubstituted or may be substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents; where aryl is as defined under (8); where R24 and R25 are identical or different and are each independently of the other hydrogen, (C<|-C4)-alkyl, (C-|-C4)-acyl, (C3-C6)-cycloalkyl, phenyl and substituted phenyl and where R21, R22, R23 are identical or different and are each independently of the others (C-|-C<|8)-alkyl, (C-|-C-|8)-alkoxy, (C3_C8)-cycloalkyl and aryl, where in the (C-|-C-|8)-nydrocarbon radicals more than one, preferably up to three, CH2 groups may be replaced by oxygen and where 3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle, it also being possible for two of the carbon radicals (for example R2^ and R22) attached to silicon together to form a cycle, the silicon atom possibly being part of this cycle, and where additionally these (C-|-Cn8)-hydrocarbon radicals with or without the variations may be substituted by one or more (in the case of halogen up to the maximum number) identical or different radicals selected from the group consisting of halogen, haloalkyl, cycloalkyl, where the substituents on the (C3-C8)-cycloalkyl or (Cs-CsJ-cycloalkenyl radicals defined above may be cis or trans with respect to the unit (X-Y) and where, in the case that the cycloalkyl group is the cyclohexyl radical and the abovementioned units are in the 1 ,4 position, preference is given to the cis configuration; or
Y is a bond; and
Ry is (C1-C2θ)-alkyl, (C2-C2θ)-alkenyl, (C2-C2θ)-alkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals and where in the alkyl, alkenyl or alkynyl radicals mentioned one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by hetero atom units such as oxygen or SiR27R28, where R27 and R28 are each (C1-C4)-alkyl, preferably methyl, and where additionally 3 to 6 atoms of these hydrocarbon radicals, which may be modified as above, may form a cycle, and where these hydrocarbon radicals with or without the variations mentioned may be substituted by one or more, preferably by up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of halogen, preferably fluorine, aryl, aryloxy, arylthio, (C3-C8)-cycloalkoxy, (C3-
CsJ-cycloalkylthio, heterocyclyl, heterocyclyloxy or (C-|-C2)-alkoxycarbonyl, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or Ry and Rz together form a five- or six-membered ring system which is linked, preferably spirocyclically, to the ring system containing the hetero atoms χ1 , and where one CH2 group may be replaced by hetero atom units such as oxygen, S(O)n where n = 0, 1 or 2 or NR29, where R29 is hydrogen, (Cη-C8)-alkyl, (C-|-C8)-alkanoyl, benzoyl, aryl or heteroaryl, where the benzoyl, aryl or heteroaryl radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, and where the ring system formed by Ry and Rz may be unsubstituted or substituted by up to three, but preferably one, substituents and where these substituents are identical or different and are each (C-|-C8)-alkyl, (C3-C8)-cycloalkyl, aryl or aryl-(Cπ-C4)-
alkyl, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or where the ring system formed by Ry and Rz together with a further benzene ring or cyclohexane ring, forms a condensed ring system, preferably the indane, 1,2,3,4-tetrahydronaphthalene, decalin or benzocycloheptane system, and where the benzene ring in these condensed systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, where in the compounds where the carbon atom between the hetero atoms X"l only carries the substituent Ry, the substituents X and Ry on the heteroaliphatic six-membered ring are preferably cis to each other; and is hydrogen or (b) is a group of the formula (III)
Y1 , Y2 and Y3 are each a group of the formula -O-, -S(O)r, where r = 0, 1 or 2 or is a group of the formula CR3lR32 , or Y1 or Y3 stands in place of a direct bond, where
R31 and R32 independently of the other are each hydrogen or methyl; m1 is 1 or 2; n1 is 1 or 2;
Z1 is a direct bond, NR33, O, S(O)s where s = 0, 1 or 2, OSO2, SO2O,
NR34SO2, SO2NR35, SiR36R37 or U-C(W)-V, where
U is a direct bond, NR38 or O; W is oxygen;
V is a direct bond, NR39 or oxygen; and
R36 and R37 are each (Cπ-C4)-alkyl or phenyl, preferably methyl;
R33, R34_ R35 R38 and R39 are identical or different and are each hydrogen, (C-|-C4)-alkyl, (C-|-C4)-alkoxy, (C-|-C4)-alkanoyl or (C3-C5)-cycloalkyl;
R°. independently of the others is (Cι-Cs)-alkyl where one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by oxygen and which, with or without the variations mentioned, may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D R43, or
R0. may be aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D2R44;
D"! and D2 are independent of one another and are each a direct bond, -O-,
-S(O)k-, -SO2O-, -OSO2-, -CO-, -OCO-, -COO-, -NR46-, -SO2NR46-,
-NR 6SO2-, -ONR46-, -NR46O-, -NR46CO-, -CONR46-, and k = 0, 1 or 2, and where R46 independently of the others is hydrogen, (C-|-C4)-alkyl, (C1-C4)- alkanoyl or (C3-C5)-cycloalkyl;
R43 and R44 independently of the other are each hydrogen, halogen, preferably fluorine, (C-|-C8. -alkyl, (C3-C8)-cycloalkyl, aryl or heterocyclyl, where in the last 3 radicals the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R49, where R49 independently of the others may be (C1-C4)-alkyl, (Cπ-C4)-haloalkyl,
(C-|-C4)-alkoxy, (Ci-C4)-haloalkoxy, cyano, nitro, halogen; or,
Y4 is a direct bond or CH2;
Z2 is oxygen;
Ru is hydrogen, (Cπ-C4)-alkyl, trifluoromethyl or (Cη-C4)-alkoxy;
W1 is a direct bond, oxygen, -CO-, -COO-, CONR52, sulfur, -C=N-,
-C=N-O- where R52 is hydrogen, (C-|-C4)-alkyl, (C-|-C4)-alkanoyl and (C3-C5)-cycloalkyl, and
R* is as defined above under (12 c).
Particularly preferred are those compounds of formula I in which
Rl is hydrogen;
R2 and R3 are each hydrogen, methyl, ethyl, propyl, methoxy, (C2-C3)-alkenyl, amino, (Cπ-C4)-alkylamino, (C-|-C4)-dialkylamino, (C2-C3)-chloro- or - fluoroalkenyl, (C2-C3)-alkynyl, trimethylsilylethynyl, (C-|-C3)-chloro- or - fluoroalkyl, methoxymethyl, halogen or cyano; or
R2 and R3 together with the ring system to which they are attached form the quinazoline or quinoline system, which may be fluorine-substituted in the carbocyclic moiety; or
R2 and R3 together with the carbon atoms to which they are attached form a saturated 6-membered ring, which may contain an oxygen or sulfur atom instead of a CH2 group;
Especially preferred compounds are those compounds where R1 is hydrogen;
R2 is methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, (C-|-C2)-fluoroalkyl or methoxymethyl;
R3 is fluorine, chlorine, bromine, cyano, vinyl, ethynyl, (C-|-C2)-fluoroalkyl, amino,
(C-|-C2)-alkylamino, (Cπ-C2)-dialkylamino or methoxy; or, in the case that A is nitrogen,
R2 and R3 form, together with the ring system to which they are attached, the quinazoline system, which may be substituted by one fluorine atom.
Other preferred compounds are those in which
X is NH;
Y is a bond; and
Z is (a) cyclopentyl or cyclohexyl, where both radicals may be substituted as above under (10) and where, in the case of cyclohexyl, 1 ,4-substitution is preferred, the substituents being cis to one another; or
(b) is a group of the formula II
Rz is hydrogen; or
(c) is a group of the formula
Y1 is CH2;
Y2 is CH2;
Y3 is CH2, O or a direct bond; m1 is 1 or
Y4 is a direct bond or CH2;
Z2 is oxygen;
Ru is hydrogen or methyl;
in particular those compounds where
Z (a) is cyclohexyl which is preferably substituted by a radical selected from the group consisting of
(C-i-C-βJ-alkyl,
(C3-C8)-cycloalkyl,
(C3-C8)-cycloalkoxy,
(C2-C8)-alkenyl,
(C2-C8)-alkynyl,
(C-i-Csr-alkoxy,
(C-|-C8)-alkoxycarbonyl,
SiR2lR22R23,
-CO-NR2 R25, aryl, heteroaryl,
O aryl,
O heteroaryl,
CH2θaryl,
CH2θheteroaryl,
(Cη-C8)-alkanediyldioxy and
(C-|-C-|3)-alkyloximino, where this substituent is in position 4 of the cyclohexyl ring and cis with respect to the -(X-Y)- unit and where, if not included in the definitions above, one or more, preferably up to three, CH2 groups in the (C-i-Cβ)-, (C2-C8)-hydrocarbon radicals mentioned may be replaced by hetero atom radicals, such as O, or SiR"! 1"Rl2",
where Rι π" and Rπ2" have the meanings of R1 1, Rl 2, and where additionally 3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle, and where these hydrocarbon radicals with or without the variations may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of hydroxyl, halogen, alkyl, haloalkyl, cycloalkyl, acyl, phenyl, substituted phenyl; heteroaryl may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents; aryl is as defined under (8);
R24 and R25 are identical or different and independently of one another are each hydrogen, (C-|-C4)-alkyl, phenyl and substituted phenyl, and R ^ , R22, R23 are identical or different and independently of one another are each (C-|-Cg)-alkyl, (C-|-C8)-alkoxy, (C3-C8)- cycloalkyl and aryl, where in the (C<|-C8)-hydrocarbon radicals more than one, preferably up to three, CH2 groups may be replaced by oxygen and 3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle, it being possible for the silicon atom to be part of this cycle, and where additionally these (C-|-C8)-hydrocarbon radicals with or without the variations may be substituted by one or more (in the case of halogen up to the maximum number) identical or different radicals selected from the group consisting of halogen, haloalkyl, cycloalkyl; or (b) is a group of the formula (II)
X1 is oxygen; Rz is hydrogen;
Ry is (C- -Ci5)-alkyl, aryl or heterocyclyl meaning a heteroaromatic ring system, where the aryl or heterocyclyl radical may be
unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals and where in the alkyl radical mentioned one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by oxygen, and where additionally 3 to 8 atoms of this alkyl radical, which may be modified as above, may form a cycle, and where this alkyl radical with or without the variations mentioned may be substituted by one or more halogen atoms (in the case of fluorine up to the maximum number of identical or different substituents), and where the substituents X and Ry on the heteroaliphatic six-membered ring are preferably cis to one another; or (c) is a group of the formula (III)
R°. independently of the others is (Cι-Cs)-alkyl where one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by oxygen, and which with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D1 R43, or
R°. may be aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number), identical or different radicals D2R44; or (d) is a group of the formula IV
where
Ru is hydrogen;
R* is (Cπ-C8)-alkyl in which one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by oxygen, and which with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D3R56 or
R* may be aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D R57.
Most particularly preferred are those compounds of the formula I in which
R1 is hydrogen;
R2 is ethyl or methoxymethyl; and
R3 is chlorine, bromine or methoxy, preferably those for which R2 is ethyl and R3 is chlorine; Other preferred compounds are those where
R4 and R5, which may be the same or different, are hydrogen, halogen, nitro, cyano, a negative charge, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heterocyclyl or optionally substituted cycloalkyl.
Particularly preferred are those compounds where
R is hydrogen, halogen, nitro, cyano, a negative charge, optionally substituted C-|-C20-alkyl, optionally substituted C2-C20-alkenyl, optionally substituted
C2_C20"a,kynyl, and
R5 is hydrogen, halogen, nitro, cyano, optionally substituted C-|.C20"a'kyl. optionally substituted C2-C20-a'kenyl, optionally substituted C2-C20"a'kynyl. optionally substituted aryl, and optionally substituted Cs-Cg-cycloalkyl.
Especially preferred are compounds where
R4 is hydrogen, halogen, C-|-C4-alkyl or a negative charge if R5 = COR5', and
R5 is hydrogen, halogen, C-j-Cβ-alkyl, Ci-Cβ-haloalkyI, C2-C8-alkenyl, C2-C8-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-Cπ-C4-alkyl, aryl, C-j-Cβ-alkoxy, (CO)R5' where R5' is Cη-Cβ-alkoxy or NR5"R5'", in which R5" and R5'", which may be the same or different, are hydrogen or Cπ-C8 alkyl or the two groups can form a ring in which optionally a CH2 is replaced by O, S or NR5"" with R5"" = C-|- C4-alkyl, hydrogen or phenyl.
Generally
R4 is hydrogen and
R5 is hydrogen or methyl
It is also preferred that
Da is a direct bond, NR70, O, S, SO, SO2 or Ua(CWa)Va, and especially a direct bond, NR70, O, S, O(CO), NR70(CO), (CO) or (CNR7""), preferably a direct bond, S, NR70(CO),O(CO) or (CO).
Preferred compounds also are those where
R 3 is hydrogen, cyano, C-|-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, Cη-Cβ-alkoxy-
Cι-C4-alkyl, C-|-C8-alkylthio-C«|-C4-alkyl, C3-C8-cycloalkyl, C4-C8- cycloalkenyl, C3-C8-cycloalkyl-C-|-C-alkyl, C4-C8-cycloalkenyl-Cπ-C4-alkyl, aryl, aryl-Cπ-C4-alkyl, heterocyclyl, heterocyclyl-Cι-C4-alkyl, in which the carbon containing can be substituted by one or more, preferably up to three, and in the case of halogen up to the maximum number of the same different groups selected from nitro, halogen cyano, hydroxy or Rη14, in which
R1 4is C-j-C4-alkyl, Cι-C4-haloalkyl, C-|-C4-alkoxy, C<|-C4-haloalkoxy; or
R113 is a negative charge when D13 = (CO)O, (SO2)O, U1"(PW1")V1"O, which replaces Qn"; each R70, which may be the same or different from any other R70, is hydrogen, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted amino, optionally substituted acyloxy, and optionally and may also form a 4 to 8 membered with R6, R1 12 or Rl 13, respectively with the Da, D12 or. D13 to which they are attached, and each R71, which may be the same or different from any other R7π, is hydrogen, nitro, cyano, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted amino or optionally substituted acyloxy;
R72 and R73 are alkyl or optionally substituted aryl; and especially
R6 is cyano, C-|-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C8-cycloalkyl, C4-C8- cycloalkenyl, aryl or heterocyclyl, in which up to three CH2 units in a carbon containing group can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO2, NR70 or Si R72R73 and these groups or their variations can also be substituted by up to three and in the case of halogen up the maximum number, of the same or different groups selected from nitro, halogen, SF5 or D^2R1 12 and these groups and their named variations should also be substituted by one or more of the same or different D12'R112 jn whjCh
D12 is a direct bond, NR70, N(O)R70, O, S, SO, SiR72R73, U'fCWJV, U1'(PWT)V V2', U2'(SO2)U3', Si(OR72)R73, Si(OR72)(OR73),NR 0O,
ONR70, NR70NR70, N=N, =N-, =N-NR70-, =N-O-, -N=, -NR 0-N= or -O-N= and
U',U1' V, V1' and V2', independently of each other are a direct bond, NR70, S or O,
W is O, S or NR71;
W1' is O or S;
U2' and U3', independently of each other are a direct bond, NR70 or O; and D12' is N(O)R70, SiOR72R73, SiOR72OR73, U'(CNR7 )V', S(CW')V, U'(CW')S,
U1'(PW1')V1'V2', U2'(SO2)U3', NR70O, ONR70, NR70NR70, N=N, =N-, =N-
NR70-, =N-O-, -N=, -NR70-N=, -O-N=, or D12' is COO or SO2O on which R1 12 is a negative charge or hydrogen, or
D12' is O(CO)NH, NR70(CO)NH, O(CS)NH, NR 0(CS)NH, (CO)NH, (CS)NH, O(CO), NR70(CO), SO2NH in which R1 12 is hydrogen;
U' and U1', independently of each other, are a direct bond, NR70, S or O
W is O, S or NR71
W1' is O or S
V, V1' and V2', independently of each other, are a direct bond, NR70, S or O'
U2' and U3', independently of each other, are NR70 or O
R 12 js hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, in which up to CH2 units in a carbon containing group can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO2, NR70 or
SiR72R73 and can also be substituted by nitro, halogen, SF5 or
D13R113 and in which two adjacent D12/D12'R1 12 together with the carbons to which they are attached can form a condensed ring comprising 4 to 6 ring atoms which can be substituted one or more halogen or C«|-C4-alkyl; or
(h) R1 12 is a negative charge for D 2' = (CO)O, (SO2)O, U1'(PW1')V1O which replaces the ion Qn_; or R112 is hydrogen for D12' = O(CO)NH, NR 0(CO)NH, O(CS)NH, NR70(CS)NH, (CO)NH, (CS)NH, O(CO), NR70(CO), SO2NH;
Dl 3 has the same meaning as D12 and R1 13 has the same meaning as Rl 2; R112 js hydrogen, cyano, C-|-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C3-C8- cycloalkyl, C4-C8-cycloalkenyl, aryl or heterocyclyl, in which up to CH2 units in a carbon containing group can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO2, NR70 or SiR72R73 and can also be substituted by up to three, in
the case of halogen up to the maximum number, of the same or different nitro, halogen, SF5 or D13R1 13 and in which two adjacent groups D12/D12'R1 12 with or without the named variations together with the carbons to which they are attached can form a condensed 4 bis 6 membered ring which can optionally be substituted with halogen or C-|-C4-alkyl; or
R 12 is a negative charge when D12' = (CO)O, (SO2)O, U1'(PWr)V1O which replaces Qn"; D^3 is a direct bond, NR70, O, S, (SO), SiR72R73, U"(CW")V", U1"(PW1")V1"V2",
U2"(SO2)U3", NR70O, ONR70, NR 0NR70, N=N, =N-, =N-NR70-, =N-O-, -
N=, -NR 0-N= or -O-N=,
U" and U1", independently of each other, are a direct bond, NR70, S or O, W" is O, S or NR'
W1" is S,
V", V1" and V2", independently of each other, are a direct bond, NR70, S or O,
U2" and U3 ", independently of each other, are a direct bond, NR70 or O;
Rl 13 is hydrogen, cyano, C-|-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C-|-C8-alkoxy- C«|-C4-alkyl, C-|-C8-alkylthio-C«|-C4-alkyl, C3-C8-cycloalkyl, C4-C8- cycloalkenyl, C3-C8-cycloalkyl-C-|-C4-alkyl, C4-C8-cycloalkenyl-Cι-C4-alkyl, aryl, aryl-C-|-C4-alkyl, heterocyclyl, heterocyclyl-Cη-C4-alkyl, and the carbon containing groups can also be substituted by up to three and, in the case of halogen up the maximum number, of the same or different nitro, halogen, cyano, hydroxy or R1 14, in which R1 14 is Cπ-C4-alkyl, Cη-C4-haloalkyl, Cπ-C4-alkoxy, C-|-C4-haloalkoxy; or
R1 13 is a negative charge when D13 = (CO)O, (SO2)O, U1(PW1)VlO, which replaces Qn";
Particularly preferred are compounds where
R® is C-|-C20-alkyl, aryl or heterocyclyl, in which these groups and their named variations can also be substituted by up to three and, in the case of halogen up the maximum number, of the same or different nitro, halogen, SF5 or
rj12R112 ano; these groups and their named variations should also be substituted by one or more of the same or different DI 2'R112_ jn which D12' JS R70ι SiOR72R73, SiOR72OR73,U'(CNR)V', S(CW')V, U'(CW)S,
U (PW1 ,)V V2, l U2,(SO2)U3', NR70O, ONR70, NR70 NR70, N=N, =N-, =N-
NR70-, =N-O-, -N=, -NR70-N= or -O-N=, or D12'is COO or SO2O, in which R112 is a negative charge or hydrogen, or
D 2' is O(CO)NH, NR70,(CO)NH, O(CS)NH, NR 0(CS)NH, (CO)NH, (CS)NH, O(CO), NR70(CO) or SO2NH, in which case R 2 is hydrogen,
U' and U1', independently of each other, are a direct bond, NR70, S or O,
W is O, S or NR70,
W1'is O or S,
V, V1' and V2', independently of each other, are a direct bond, NR70, S or O,
U2' and U3', independently of each other a direct bond, NR70 or O,
Even more preferred are compounds where
R6 is aryl or heteroaryl, in which these groups and their named variations can also be substituted by up to three and, in the case of halogen up the maximum number, of the same or different nitro, halogen, SF5 or Dl 2R"! l 2> and these groups and their named variations should also be substituted by one or more of the same or different Dπ2 R112, in which
D12 is a direct bond, O, U'(CW')V, U (PW1 ,)V V2', U2'(SO2)U3', in which
U' and U1', independently of each other, are a direct bond or O, W is O or S ,
W'is O or S,
V, V"1' and V2', independently of each other, are a direct bond, NR70, S or O,
U2' and U3', independently of each other are a direct bond or O, or
D12' is U'(CW')S, U (PW1')Vl'v2', U2'(SO2)U3', or
Dl2' is COO or SO2O, in which Rπ π2 is a negative charged or hydrogen, or
D12' is O(CO)NH, NR70(CO)NH, O(CS)NH, NR 0(CS)NH, (CO)NH, (CS)NH, O(CO), NR 0(CO) or SO2NH in which case R1 2 is hydrogen,;
U' and U1', independently of each other.are direct bond or O,
W is O or S
W1' is O or S
V1' or V2', independently of each other, are a direct bond, NR70, S or O,
U2' is O, and
U3' is R70 or O.
In the above formulae (I) to (IV), the radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and the corresponding unsaturated and/or substituted radicals can in each case be straight-chain or branched in the carbon skeleton. Unless specifically mentioned, the lower carbon skeletons, for example those having 1 to 6 carbon atoms or, in the case of unsaturated groups, 2 to 6 carbon atoms, are preferred for these radicals, alkyl radicals, also in the composite meanings such as alkoxy, haloalkyl and the like, are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyl radicals, hexyl radicals, such as n-hexyl, i-hexyl and 1 ,3-dimethylbutyl, heptyl radicals, such as n-heptyl, 1-methylhexyl and 1 ,4-dimethylpentyl; alkenyl and alkynyl radicals have the meanings of the unsaturated radicals which are possible and which correspond to the alkyl radicals; alkenyl is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl; alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl.
Cycloalkyl is a carbocyclic saturated ring system preferably having 3 - 8 carbon atoms, for example cyclopropyl, cyclopentyl or cyclohexyl, but also bicyclic systems, for example the norbornyl group, the bicyclo[2.2.2]octane radical and tricyclic systems, for example adamantyl.
Halogen is, for example, fluorine, chlorine, bromine or iodine. Haloalkyl, haloalkenyl and haloalkynyl are alkyl, alkenyl and alkynyl, respectively, which are partially or fully substituted by halogen, preferably by fluorine, chlorine and/or bromine, in particular by fluorine or chlorine, for example monohaloalkyl, perhaloalkyl, CF3, CHF2, CH2F,
CF3CF2, CH2FCHCI, CCI3, CHCI2, CH2CH2CI; haloalkoxy is, for example, OCF3,
OCHF2, OCH2F, CF3CF2O, OCH2CF3 and OCH2CH2CI; the same applies analogously to haloalkenyl and other halogen-substituted radicals.
A hydrocarbon radical is a straight-chain, branched or cyclic and saturated or unsaturated aliphatic or aromatic hydrocarbon radical, for example alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or aryl; preferably, a hydrocarbon radical is alkyl, alkenyl or alkynyl having up to 12 carbon atoms or cycloalkyl having 3, 4, 5, 6 or 7 ring atoms or phenyl; the same applies analogously to a hydrocarbon radical in a hydro- carbonoxy radical.
aryl is a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl.
A heterocyclic radical or ring (heterocycle) can be saturated, unsaturated or heteroaromatic; it preferably contains one or more hetero units in the ring, i.e. hetero atoms or ring members, including substituted hetero atoms, preferably selected from the group consisting of N, O, S, SO, SO2; it is preferably an aliphatic heterocyclyl radical having 3 to 7 ring atoms or a heteroaromatic radical having 5 or 6 ring atoms and it contains 1 , 2 or 3 hetero units. The heterocyclic radical can be, for example, a heteroaromatic radical or ring (heteroaryl), for example a mono-, bi- or polycyclic aromatic system in which at least 1 ring contains one or more hetero atoms, in particular an aromatic system in which at least 1 , preferably up to 4, in particular up to 2 CH are replaced by N and/or at least 1 , preferably up to 3, -CH=CH-units is replaced by NH, S or O, adjacent oxygen atoms being excluded, for example pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, thienyl, thiazolyl, oxazolyl, furyl, pyrrolyl, pyrazolyl and imidazolyl, or it is a partially or fully hydrogenated radical such as oxiranyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, morpholinyl, tetrahydrofuryl. Substituents which are suitable for a substituted heterocyclic radical are the substituents mentioned further below, and additionally oxo. The oxo group can also be present on the hetero ring atoms, which can exist at various oxidation levels, for example in the case of N and S.
Substituted radicals, such as substituted hydrocarbon radicals, for example substituted alkyl, alkenyl, alkynyl, aryl, phenyl and benzyl, or substituted heterocyclyl or heteroaryl, are, for example, a substituted radical derived from the unsubstituted skeleton, the substituents being, for example, one or more, preferably 1, 2 or 3, radicals selected from the group consisting of halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxy, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino, such as acylamino, mono- and dialkylamino, and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkyl- sulfonyl and, in the case of cyclic radicals, also alkyl, cycloalkyl and haloalkyl; the term "substituted radicals" such as substituted alkyl etc. includes as substituents, in addition to the saturated hydrocarbon-containing radicals mentioned, corresponding unsaturated aliphatic and aromatic radicals, such as alkenyl, alkynyl, alkenyloxy, alkynyloxy, phenyl, phenoxy, etc., with or without substitution. Preferred among the radicals having carbon atoms are those having 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms. Preferred substituents are generally selected from the group consisting of halogen, for example fluorine and chlorine, (Cι-C4)-alkyl, preferably methyl or ethyl, (C<j-C4)-haloalkyl, preferably trifluoromethyl, (C-|-C4)-alkoxy, preferably methoxy or ethoxy, (C-|-C4)-haloalkoxy, nitro and cyano. Especially preferred are the substituents methyl, methoxy and chlorine.
Mono- or disubstituted amino is a chemically stable radical selected from the group consisting of the substituted amino radicals which are N-substituted, for example by one or two identical or different radicals selected from the group consisting of alkyl, alkoxy, acyl and aryl; preferably monoalkylamino, dialkylamino, acylamino, arylamino, N-alkyl-N-arylamino and N-heterocycles; preference is given to alkyl radicals having 1 to 4 carbon atoms; aryl is preferably phenyl or substituted phenyl; acyl is defined as indicated further below and is preferably (Cπ-C4)-alkanoyl. The same applies analogously to substituted hydroxylamino or hydrazino.
Unsubstituted or substituted phenyl is preferably phenyl which is unsubstituted or mono- or polysubstituted, preferably up to trisubstituted, by identical or different radicals selected from the group consisting of halogen, (C-|-C4)-alkyl, (C-|-C4)-alkoxy,
(Cι-C4)-haloalkyl, (Cπ-C4)-haloalkoxy and nitro, for example o-, m- and p-tolyl, dimethylphenyl radicals, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluoro- and -trichlorophenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.
An acyl radical is the radical of an organic acid, for example the radical of a carboxylic acid and radicals of acids derived therefrom, such as thiocarboxylic acid, iminocarboxylic acids with or without N-substitution, or the radical of carbonic monoesters, carbamic acid with or without N-substitution, sulfonic acids, sulfinic acids, phosphonic acids, phosphinic acids. Acyl is, for example, formyl, alkylcarbonyl such as [(C-j-C4)alkyl]carbonyl, phenylcarbonyl, alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl and other radicals of organic acids. In each case, the radicals may be substituted even further in the alkyl or phenyl moiety, for example in the alkyl moiety by one or more radicals selected from the group consisting of halogen, alkoxy, phenyl and phenoxy; examples of substituents in the phenyl moiety are the substituents already mentioned further above in general for substituted phenyl.
Furthermore, in the above formulae the term "dimethyl-(C-|-C8)-alkylsilylethynyr denotes, for example, the trimethylsilylethynyl or the tert-butyldimethylsilylethynyl group; the term "(Cη-C4)-hydroxyalkyl" denotes, for example, the hydroxymethyl,
1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxy-1-methylethyl or the 1-hydroxypropyl group; the term "(C-|-C4)-alkanoyl" denotes, for example, the formyl, acetyl, propionyl,
2-methylpropionyl or butyryl group; the term "(C«|-C<|2)-alkanoyl" denotes, for example, the abovementioned radicals and, for example, the valeroyl, pivaloyl, hexanoyl, decanoyl or the dodecanoyl group; the term "(C2-C4)-haloalkanoyl" denotes a (C-|-C4)-alkanoyl group in which the hydrogen atoms are partly, in the case of fluorine partly or wholly, replaced by halogen atoms, preferably fluorine or chlorine; the term "(C2-Cπ2)-haloalkanoyl" denotes a (C-|-C2o)-alkanoyl group in which the hydrogen atoms are partly, in the case of fluorine partly or wholly, replaced by halogen atoms, preferably fluorine or chlorine; the term "cyano-(C-|-C4)-alkyl" denotes a cyanoalkyl group whose hydrocarbon radical has the meanings given for the term "(C-|-C4)-alkyl"; the term "(C-|-C4)-alkylamino" denotes, for example, methylamino, ethylamino, isopropylamino;
the term "(Cπ-C4)-dialkylamino" denotes, for example, dimethylamino, N-ethyl-N- methylamino, diethylamino, the term "(C1-C4)-alkoxycarbonyl" denotes, for example, the methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl or tert-butoxycarbonyl group; the term "(Cπ-Ci2)-alkoxycarbonyl" denotes the abovementioned radicals and, for example, the hexyloxycarbonyl, 2-methylhexyloxycarbonyl, decyloxycarbonyl or dodecyloxycarbonyl group; the term "(C-|-C4)-haloalkoxycarbonyl" denotes a (C-|-C4)-alkoxycarbonyl group in which one or more, in the case of fluorine possibly all, hydrogen atoms are replaced by halogen, preferably fluorine or chlorine; the term "(C<|-C4)-haloalkylthio" denotes a (C-|-C4)-alkylthio group in which one or more, in the case of fluorine possibly all, hydrogen atoms of the hydrocarbon moiety are replaced by halogen, in particular chlorine or fluorine; the term "(Cι-C4)-alkylsulfinyl" denotes, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfinyl group; the term "(Cι-C4)-alkylsulfonyl" denotes, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfonyl group; the terms "(C1-C4)-haloalkylsulfinyl" and "(C-|-C4)-haloalkylsulfonyl" denote (C-J-C4)- alkylsuifinyl and -sulfonyl radicals having the abovementioned meanings in which one or more, in the case of fluorine possibly all, hydrogen atoms of the hydrocarbon moiety are replaced by halogen, in particular chlorine or fluorine; the term "(Cπ-C4)-alkoxy-(C1-C4)-alkyl" denotes, for example, a 1-methoxyethylene group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a methoxymethyl or ethoxymethyl group, a 3-methoxypropyl group or a 4-butoxybutyl group; the terms "(Cι-C4)-haloalkoxy-(C1-C4)-alkyl", "(C1-C4)-alkoxy-(Cι-C )-haloalkyr and
"(Cι-C4)-haloalkoxy-(C-|-C4)-haloalkyl" denote (C«|-C4)-alkoxy-(Cι-C4)-alkyl radicals having the abovementioned meanings where one or more, in the case of fluorine possibly all, hydrogen atoms of the appropriate hydrocarbon moieties are replaced by halogen, preferably chlorine or fluorine; the term "(C-|-C4)-alkylthio-(C-|-C4)-alkyr denotes, for example, methylthiomethyl, ethylthiomethyl, propylthiomethyl, 2-methylthioethyl, 2-ethylthioethyl or
3-methylthiopropyl; the term "arylthio" denotes, for example, the phenylthio or the 1- or 2-naphthylthio group;
the term "aryloxy" denotes, for example, the phenoxy- or 1- or 2-naphthyloxy group; the term "heterocyclyloxy" or "heterocyclylthio" denotes one of the abovementioned heterocyclic radicals which are linked via an oxygen or sulfur atom; the term "cycloalkoxy" or "cycloalkylthio" denotes one of the abovementioned cycloalkyl radicals which are linked via an oxygen or sulfur atom; the term "aroyl" denotes, for example, the benzoyl, naphthoyl or the biphenylcarbonyl group; the term "aryl-(Cι-C4)-alkanoyl" denotes, for example, the phenylacetyl,
3-phenylpropionyl, 2-phenylpropionyl, 2-methyI-2-phenylpropionyl, 4-phenylbutyryl or the naphthylacetyl group; the term "(C3-C8)-cycloalkyl-(Cπ-C4)-alkanoyl" denotes, for example, the cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cyclohexylacetyl or the cyclohexylbutyryl group; the term "heterocyclyl-(C-|-C4)-alkanoyl" denotes, for example, the thenoyl, furoyl, nicotinoyl, thienylacetyl or the pyridinepropionyl group; the term "(C3-C8)-cycloalkoxycarbonyl" denotes, for example, the cyclobutyl- oxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl or the cycloheptyloxycarbonyl group; the term "(C3-C8)-cycloalkyl-(Cι-C4)-alkoxycarbonyl" denotes, for example, the cyclopropylmethoxycarbonyl, cyclobutylmethoxycarbonyl, cyclopentyloxy- methoxycarbonyl, cyclohexyloxymethoxycarbonyl, 1-(cyclohexyl)-ethoxycarbonyl or the 2-(cyclohexyl)ethoxycarbonyl group; the term "aryl-(Cπ-C4)-alkoxycarbonyl" denotes, for example, the benzyloxycarbonyl,
1-naphthylmethoxycarbonyl, 2-naphthylmethoxycarbonyl, 1-phenylethoxycarbonyl or the 2-phenylethoxycarbonyl group; the term "heterocyclyl-(C-|-C4)-alkoxycarbonyl" denotes, for example, the thienylmethoxycarbonyl, furylmethoxycarbonyl, tetrahydrofurylmethoxycarbonyl or the pyridylethoxycarbonyl group; the term "aryloxycarbonyl" denotes, for example, the phenoxycarbonyl, naphthoxycarbonyl or the biphenyloxycarbonyl group; the term "heterocyclyloxycarbonyl" denotes, for example, the tetrahydropyran-4- oxycarbonyl group; the term "(C<|-C2o)-alkanoyloxy" denotes, for example, the formyloxy, acetoxy, propionyloxy, butyryloxy, pivaloyloxy, valeroyloxy or the hexanoyloxy group;
the term "(C2-C2θ)-haloalkanoyloxy" denotes a (C2-C2o)-alkanoyloxy group in which one or more, in the case of fluorine possibly all, hydrogen atoms of the hydrocarbon moiety are replaced by halogen, in particular fluorine or chlorine; the term "(C3-C8)-cycloalkanoyloxy" denotes, for example, the cyclopropanoyloxy, cyclobutenoyloxy, cyclopentanoyloxy, cyclohexanoyloxy or the cycloheptanoyloxy group; the term "(C3-C8)-cycloalkyl-(C-|-C4)-alkanoyloxy" denotes, for example, the cyclopropylcarbonyloxy, cyclopropylacetoxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, cyclohexylacetoxy or the 4-cyclohexylbutyryloxy group; the term "aroyloxy" denotes, for example, the benzoyloxy or the naphthoyloxy group; the term "aryl-(C-|-C4)-alkanoyioxy" denotes, for example, the benzoyloxy, naphthoyloxy, biphenylcarbonyloxy, phenylacetoxy or the phenylbutyryloxy group; the term "heterocyclyl-(Cι-C4)-alkanoyloxy" denotes, for example, the thienylcarbonyloxy, thienylacetoxy, pyridylcarbonyloxy or the pyrimidinylcarbonyloxy group; the term "(C-|-C2θ)-alkylsulfonyloxy" denotes, for example, the methane-, ethane-, butane- or hexanesulfonyloxy group; the term "arylsulfonyloxy" denotes, for example, the phenylsulfonyloxy or the toluenesulfonyloxy group; a "bivalent hydrocarbon chain" denotes a radical which is derived from n-alkanes or n- alkenes by removal of in each case one hydrogen atom from each of the two terminal carbon atoms of the chain, such as methylene, ethanediyl, trimethylene, tetramethylene; the term "(Cπ-Ci8)-alkanediyldioxy" denotes a bivalent radical derived from (C-|-Cπ8)- alkanes by replacement of two hydrogen atoms by two -O- radicals.
Furthermore, the definition that "in the alkyl, alkenyl or alkynyl radicals mentioned one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O)x where x = 0, 1 or
2, NR26 or SiR27R28, where R26 is hydrogen, (C-|-C4)-alkyl, (Cπ-C4)-alkoxy or
(C-j-C4)-alkanoyl and where R27 and R28 are each (C1-C4)-alkyl, preferably methyl, and where additionally 3 to 12 atoms of these hydrocarbon radicals, which may be modified as above, may form a cycle and where these hydrocarbon radicals with or
without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals selected from the group consisting of halogen, aryl, aryloxy, arylthio, cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, alkanoyl, cycloalkanoyl, haloalkanoyl, aroyl, arylalkanoyl, cycloalkylalkanoyl, heterocyclylalkanoyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, arylalkoxycarbonyl, heterocyclylalkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, alkanoyloxy, haloalkanoyloxy, cycloalkanoyloxy, cycloalkylalkanoyloxy, aroyloxy, arylalkanoyloxy, heterocycloylalkanoyloxy, alkylsulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyano or nitro, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents" denotes, for example: alkoxyalkyl radicals, for example the methoxymethyl, methoxyethyl or ethoxyethyl group; or alkoxyalkoxyalkyl radicals, for example the methoxy- or the ethoxyethoxyethyl group; or alkylthioalkyl radicals, for example the methyl- or the ethylthioethyl group; or alkylsulfinylalkyl radicals, for example the methyl- or ethylsulfinylethyl group; or alkylsulfonylalkyl radicals, for example the methyl- or ethylsulfonylethyl group; or alkyldialkylsilylalkyl radicals, preferably alkyldimethylsilylalkyl radicals, for example the trimethylsilylmethyl or the trimethylsilylethyl group; or trialkylsilyl radicals, preferably alkyldimethylsilyl radicals, for example the trimethylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl or the octyldimethylsilyl group; or cycloalkyldialkylsilyl radicals, preferably cycloalkyldimethylsilyl radicals, for example the cyclohexyldimethylsilyl group; or aryldialkylsilyl radicals, preferably aryldimethylsilyl radicals, for example the phenyldimethylsilyl group; or arylalkyldialkylsilyl radicals, preferably aryldimethylsilyl radicals, for example the benzyldimethylsilyl or the phenylethyldimethylsilyl group; or alkanoylalkyl radicals, for example the acetylmethyl or the pivaloylmethyl group; or cycloalkanoylalkyl radicals, for example the cyclopropylcarbonylmethyl or the cyclohexylcarbonylmethyl group; or
haloalkanoylalkyl radicals, for example the trifluoro- or trichloroacetylmethyl group; or aroylalkyl radicals, for example the benzoyl- or naphthoylalkyl radicals, for example the phenylacetylmethyl group; or heterocyclylcarbonylalkyl radicals, for example the thienyl- or pyridylacetylmethyl group; or arylalkyl radicals, for example the benzyl, the 2-phenylethyl, the 1-phenylethyl, the 1-methyl-1-phenylethyl group, the 3-phenylpropyl, the 4-phenylbutyl group, the 2-methyl-2-phenylethyl group or the 1 -methyl- or 2-methylnaphthyl group; or heterocyclylalkyl radicals, for example the thienylmethyl, pyridylmethyl, furfuryl-, tetrahydrofurfuryl-, tetrahydropyranylmethyl- or the 1 ,3-dioxalane-2-methyl group; or aryloxyalkyl radicals, for example the phenoxymethyl or naphthoxymethyl group; or cycloalkyl radicals, monocyclic such as, for example, the cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl radical, bicyclic such as, for example, the norbornyl radical or the bicyclo[2.2.2]octane radical or condensed such as the decahydronaphthyl radical; alkylcycloalkyl radicals, for example the 4-methyl- or the 4-tert-butylcyclohexyl group or the 1-methylcyclopropyl, -cyclobutyl, -cyclopentyl- or -cyclohexyl group; cycloalkylalkyl radicals, for example the cyclohexylmethyl or -ethyl group; or else haloalkyl derivatives of the appropriate groups, for example haloalkyl, haloalkoxyalkyl, alkoxyhaloalkyl, haloalkylcycloalkyl or halocycloalkyl radicals. This applies correspondingly to similar definitions.
The illustration given above applies correspondingly to homologs or to radicals derived therefrom.
In addition to the cis/trans isomerism mentioned, some of the compounds of the formula I have one or more asymmetric carbon atoms or stereoisomers at double bonds. Enantiomers or diastereomers may therefore be present. The invention embraces both the pure isomers and mixtures thereof. Mixtures of diastereomers can be separated into the components by conventional methods, for example by selective crystallization from suitable solvents or by chromatography. Racemates can be separated into the enantiomers by conventional methods, for example by salt formation with an optically active acid, separation of the diastereomeric salts and liberation of the pure enantiomers using a base.
The invention furthermore relates to a process for preparing compounds of the formula I which comprises reacting a compound of the formula (V)
where G is CH or N and R1 , R2, R3 X, Y and Z are each as defined under formula I, with an electrophile of the formula (VI)
L-R (VI) where R is as defined under formula I and L is a leaving group, for example halogen, alkylthio, alkanesulfonyloxy or arylsulfonyloxy, alkylsulfonyl or arylsulfonyl, preferably halogen, if appropriate with the addition of salts such as, for example, AgBF4, AgNO3 or Nal, replacing, if appropriate, the anion of the compounds obtained in this manner by other anions, similarly to known methods [for example Liebigs Ann. Chem. 1978, 1937; Methoden der Org. Chemie/Houben-Weyl (D. Klamann, Ed.), 4th Edition, Vol. E16a, Part 2, p. 1008 ff., Thieme, Stuttgart 1990].
The substitution reaction described above is known in principle [for example Methoden der Org. Chemie/Houben-Weyl (D. Klamann, Ed.), 4th Edition, Vol. E16a, Part 2, p. 997 ff., Thieme, Stuttgart 1990, Liebigs Ann. Chem. 621 (1959) 106; Arch. Pharm. (Weinheim) 328 (1995) 531].
The structures (V) and (VI) can be varied within wide limits.
The abovementioned reaction is carried out in a temperature range from 20 to 150"C, if appropriate in an inert organic solvent such as acetonitrile, acetone, 2-butanone, N.N-dimethylforrnamide, N.N-dimethylacetamide, dimethyl sulfoxide, N- methylpyrrolidin-2-one, dioxane, tetrahydrofuran, 4-methyl-2-pentanone, methanol, ethanol, butanol, ethylene glycol, ethylene glycol dimethyl ether, toluene, chlorobenzene or xylene. It is also possible to use mixtures of the solvents mentioned.
Most of the compounds of the formula (V) required as starting materials are known from the literature [for example DE-A-4 438 807, WO-A-96 11 913, WO-A-96 11 924,
DE-4 343 250, WO-A-95 07 890, WO-A-94 21 613, DE-A-4 208 254], or they can be prepared similarly to known methods.
Compounds of the formula (VI) are commercially available, or they can be obtained by processes known in principle [for example: Verhe, De Kimpe, in "The Chemistry of Functional Groups, Supplement D" (Patai, Rappoport, Eds.), Part 1, p. 813 ff., Wiley, New York, 1983].
While being tolerated well by plants and having favorable toxicity toward warmblooded animals, the active substances are suitable for controlling animal pests, especially insects, arachnids, helminths and molluscs, and very particularly preferably for controlling insects and arachnids, which are encountered in agriculture, in animal breeding, in forestry, in the protection of stored products and materials, and in the hygiene sector. They are active against normally sensitive and resistant species and against all or certain stages of development. The abovementioned pests include:
From the order of the Acarina, for example, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp.,
Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,
Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp. and Eutetranychus spp..
From the order of the Isopoda, for example, Oniscus asselus, Armadium vulgar and
Porcellio scaber.
From the order of the Diplopoda, for example, Blaniulus guttulatus.
From the order of the Chilopoda, for example, Geophilus caφophagus and Scutigera spp.
From the order of the Symphyla, for example, Scutigerella immaculata.
From the order of the Thysanura, for example, Lepisma saccharina.
From the order of the Collembola, for example, Onychiurus armatus.
From the order of the Orthoptera, for example, Blatta orientalis, Periplaneta americana, Leucophaea madeirae, Blatella germanica, Acheta domesticus,
Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and
Schistocerca gregaria.
From the order of the Isoptera, for example, Reticulitermes spp.
From the order of the Anoplura, for example, Phylloera vastatrix, Pemphigus spp., Pediculus humanus coφoris, Haematopinus spp. and Linognathus spp. From the order of the Mallophaga, for example, Trichodecte spp. and Damalinea spp. From the order of the Thysanoptera, for example, Hercinothrips femoralis, Thrips tabaci and Frankliniella spp.
From the order of the heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.
From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis spp., Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arandinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelus bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.
From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Caφocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cuaphalocrocis spp. and Manduca spp.
From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylloides chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonumus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrynchus assimilis, Hypera postica, Dermestes spp., Trogorma, Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conorus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica and Lissorhoptus spp.
From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp.,
Lasius spp., Monomorium pharaonis and Vespa spp.
From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp.,
Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hypobosca spp., Stomoxys spp., Oestrus spp., Hyporma spp., Tabanus spp., Tannia spp., Bibio hortulanus,
Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and
Tipula paludosa.
From the order of the Siphonaptera, for example, Xenopsylla cheopsis and
Ceratophyllus spp.
From the order of the Arachnida, for example, Scorpio maurus and Latrodectus mactans.
From the class of the helminths, for example, Haemonchus, Trichostrongulus,
Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostrongulus,
Ancylostoma, Ascaris and heterakis and also Fasciola.
From the class of the Gastropoda, for example, Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp. and Oncomeiania spp.
From the class of the Bivalva, for example, Dreissena spp.
The plant-parasitic nematodes which can be controlled in accordance with the invention include, for example, the root-parasitic soil nematodes such as, for example, those of the genera Meloidogyne (root-knot nematodes, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica), heterodera and Globodera (cyst-forming nematodes, such as Globodera rostochiensis, Globodera pallida, heterodera trifolii) and of the genera Radopholus (such as Radopholus similis), Pratylenchus (such as Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus),
Tylenchulus (such as Tylenchulus semipenetrans), Tylenchorhynchus (such as Tylenchorhynchus dubius and Tylenchorhynchus claytoni), Rotylenchus (such as Rotylenchus robustus), Helicotylenchus (such as Helicotylenchus multicinctus), Belonoaimus (such as Belonoaimus longicaudatus), Longidorus (such as Longidorus elongatus), Trichodorus (such as Trichodorus primitivus) and Xiphinema (such as Xiphinema index).
The compounds according to the invention can also be used to control the nematode genera Ditylenchus (stem parasites, such as Ditylenchus dipsaci and Ditylenchus destructor), Aphelenchoides (leaf nematodes, such as Aphelenchoides ritzemabosi) and Anguina (leaf-gall nematodes, such as Anguina tritici).
The invention also relates to compositions, especially insecticidal and acaricidal compositions, which comprise the compounds of the formula I in addition to suitable formulation auxiliaries.
The compositions according to the invention comprise the active substances of the formulae I in general in a proportion of from 1 to 95% by weight. They can be formulated in various ways depending on the biological and/or chemicophysical parameters which prevail. Possible formulations which are suitable are therefore:
wettable powders (WP), emulsifiable concentrates (EC), aqueous solutions (SL), emulsions, sprayable solutions, oil- or water-based dispersions (SC), suspoemulsions (SE), dusts (DP), seed-dressing products, granules in the form of microgranules, spray granules, coated granules and adsorption granules, water-dispersible granules (WG), ULV formulations, microcapsules, waxes or baits.
These individual types of formulation are known in principle and are described, for example, in:
Winnacker-Kϋchler, "Chemische Technologie" [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th ed. 1986; van Falkenberg, "Pesticides Formulations", Marcel Dekker N.Y., 2nd ed. 1972-73; K. Martens, "Spray Drying Handbook", 3rd ed. 1979, G. Goodwin Ltd. London.
The formulation auxiliaries required, such as inert materials, surfactants, solvents and other additives, are likewise known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell N.J.; H.v. Olphen, "Introduction to Clay Colloid Chemistry", 2nd ed., J. Wiley & Sons, N.Y.; Marsden, "Solvents Guide", 2nd ed., Interscience, N.Y. 1950; McCutcheon's, "Detergents and Emulsifiers Annual", MC Publ. Coφ., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schόnfeldt, "Grenzflachenaktive Athylenoxidaddukte" [Surface-active
ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1967; Winnacker-Kϋchler, "Chemische Technologie", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986.
Based on these formulations, it is also possible to produce combinations with other pesticidally active substances, fertilizers and/or growth regulators, for example in the form of a readymix or a tank mix. Wettable powders are preparations, uniformly dispersible in water, which contain, beside the active substance and in addition to a diluent or inert material, wetting agents, for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, alkyl- or alkylphenolsulfonates, and dispersing agents, for example sodium ligninsulfonate or sodium 2,2'-dinaphthylmethane-6,6,-disulfonate. Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons, with addition of one or more emulsifiers. As emulsifiers, the following can be used, for example: calcium salts of alkylaryl- sulfonates, such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.
Dusts are obtained by grinding the active substance with finely divided solid substances, for example talc, natural clays such as kaolin, bentonite, pyrophillite or diatomaceous earth. Granules can be prepared either by atomizing the active substance onto adsoφtive, granulated inert material or by applying active substance concentrates onto the surface of carrier materials such as sand or kaolinites, or of granulated inert material, by means of adhesives, for example polyvinyl alcohol or sodium polyacrylate, or alternatively mineral oils. Suitable active substances can also be granulated in the fashion conventional for the preparation of fertiliser granules, if desired as a mixture with fertilisers.
In wettable powders, the concentration of active substance is, for example, from approximately 10 to 90% by weight, the remainder to 100% by weight being composed of customary formulation components. In the case of emulsifiable concentrates, the concentration of active substance may be from approximately 5 to 80% by weight. Dust formulations comprise in most cases from 5 to 20% by weight of active substance, sprayable solutions from about 2 to 20% by weight. In the case of
granules, the content of active substance depends partly on whether the active compound is in liquid or solid form and on which granulation auxiliaries, fillers, etc. are being used.
In addition, the abovementioned formulations of active substance comprise, if appropriate, the adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers which are customary in each case.
The concentrates, which are in the commercially customary form, are if appropriate diluted in the customary manner for their use, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and some microgranules. Dust and granule preparations, and also sprayable solutions, are normally not diluted any further with other inert substances before being used.
The application rate required varies with the external conditions, such as temperature and humidity among others. It can fluctuate within wide limits, for example between 0.0005 and 10.0 kg/ha or more of active substance, but is preferably between 0.001 and 5 kg/ha.
The active substances according to the invention may be present in their commercially customary formulations, and in the application forms prepared from these formulations, as mixtures with other active substances, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth regulators or herbicides.
The active substance content of the use forms prepared from the commercially customary formulations can be from 0.00000001 to 95% by weight of active substance, preferably between 0.00001 and 1% by weight.
Application is effected in a conventional fashion, matched to the use forms.
The active substances according to the invention are also suitable for controlling ecto- and endoparasites in the veterinary medicine sector or in the sector of animal husbandry.
The active substances according to the invention are in this case applied in a known fashion, such as by oral application in the form of, for example, tablets, capsules, potions or granules, by dermal application in the form of, for example, dipping, spraying, pouring-on and spotting-on and powdering, and also by parenteral application in the form of, for example, injection.
The novel compounds, according to the invention, of the formula I can accordingly also be employed particularly advantageously in livestock husbandry (for example cattle, sheep, pigs and poultry such as chickens, geese etc.). In a preferred embodiment of the invention, the novel compounds, if appropriate in suitable formulations (cf. above) and if appropriate with the drinking water or feed, are administered orally to the animals. Since they are excreted in active form in the droppings, the development of insects in the animal droppings can be prevented very simply in this fashion. The dosages and formulations suitable in each case are particularly dependent on the type and stage of development of the productive animals and also on the degree of infestation, and can easily be determined and fixed by conventional methods. In the case of cattle, the novel compounds can be employed, for example, in dosages of 0.01 to 1 mg/kg of body weight.
Some compounds of the formula I according to the invention are also distinguished by an fungicidal action. Fungal pathogens which have already penetrated the plant tissue can be successfully subjected to curative control. This is particularly important and advantageous in the case of those fungal diseases which can no longer be controlled effectively with the otherwise customary fungicides when infection has taken place already. The spectrum of action of the claimed compounds embraces various economically important phytopathogenic fungi, for example Plasmopara viticola, Phytophthora infestans, Erysiphe graminis, Piricularia oryzae, Pyrenophora teres, Leptosphaeria nodorum, Pellicularia sasakii and Puccinia recondita.
In addition, the compounds according to the invention are also suitable for use in technical fields, for example as wood preservatives, as preservatives in paints, in cooling lubricants for metalworking, or as preservatives in drilling and cutting oils.
The active substances according to the invention in their commercially customary formulations can be employed either alone or in combination with other fungicides known from the literature.
The abovementioned components for combinations are known active substances of which many are described in The Pesticide Manual, edited by C D S Tomlin, 11th edition (1997), bublished by the British Crop Protection Council. The active substance content of the use forms prepared from commercially customary formulations can vary within wide limits, and the concentration of active substance in the use forms can be from 0.0001 up to 95% by weight of active substance, preferably between 0.0001 and 1 % by weight. The formulations are applied in a customary manner adapted to suit the use forms.
The examples which follow illustrate the invention without limiting it thereto.
A. Formulation Examples
a) A dust is obtained by mixing 10 parts by weight of active substance and 90 parts by weight of talc as inert material and comminuting in a hammer mill.
b) A wettable powder which is easily dispersible in water is obtained by mixing 25 parts by weight of active substance, 65 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurinate as wetting and dispersing agent, and grinding in a pinned disk mill.
c) A dispersion concentrate which is easily dispersible in water is prepared by mixing 40 parts by weight of active substance with 7 parts by weight of a sulfosuccinic monoester, 2 parts by weight of a sodium ligninsulfonate and 51 parts by weight of water and grinding in a ball mill to a fineness of below 5 microns.
d) An emulsifiable concentrate can be prepared from 15 parts by weight of active substance, 75 parts by weight of cyclohexane as solvent and 10 parts by weight of ethoxylated nonylphenol (10 EO) as emulsifier.
e) Granules can be prepared from 2 to 15 parts by weight of active substance and an inert granule carrier material such as attapulgite, granulated pumice and/or quartz sand. It is advantageous to use a suspension of the wettable
powder of Example b) with a solids content of 30% which is sprayed onto the surface of attapulgite granules which are then dried and intimately mixed. The proportion by weight of the wettable powder in this case is about 5% and that of the inert carrier material is about 95% of the finished granules.
B. Preparation examples
Example 1
5-chloro-1-{4-[(diphenoxyphosphoryl)oxy]phenacyl)-6-ethyl- 4-(cis-phenylcyclohexylamino)pyrimidinium bromide
2.00 g of 5-chloro-6-ethyl-4-(cis-4-phenylcyclohexylamino)pyrimidine and 1.94 g of 4-(2-bromoacetyl)phenyl diphenyl phosphate were stirred in boiling acetone for 10 h. The solvent was removed under reduced pressure. Recrystallisation from methylene chloride/ethyl acetate gave the title product, m.p. 179-182°C.
Preparation of the starting material
4-(2-bromoacetyl)phenyl diphenyl phosphate
To 5.00 g of 4-acetylphenyl diphenyl phosphate dissolved in chloroform was added 0.69 ml of bromine, slowly, with stirring. The mixture was stirred at room temperature for 30 minutes and then quenched with water. The organic layer was washed twice with water and dried with sodium sulfate. Evaporation of the solvent gave the crude title product as a yellow oil, which was pure enough for further reactions.
4-acetylphenyl diphenyl phosphate
To 20 g of 4-hydroxyacetophenone dissolved in dimethylformamide were added 16.33 g of triethylamine followed by 39.46 g of O,O-diphenyl chlorophosphate. The reaction mixture was stirred at room temperature for 3J hours and then poured into water. The mixture was extracted repeatedly with dichloromethane and the combined organic layers were washed with water and dried with sodium sulfate. The solvent was removed and the residue purified by chromatography (silica gel: dichloromethane/methanol = 95:5), to give the title product as a yellow oil.
The compounds of the tables below were obtained similarly to [Examples 1 to 3.
In a similar manner the following compounds are obtained:
The formula implies that although the substituted methyl radical is shown attached to the 1 -position, it cannot be excluded that the attachment is to the nitrogen in position 3
There was also obtained:
5-chloro1-(cyanomethyl)-6-ethyl-4-(cis-4-phenylcyclohexylamino)pyrimidinium bromide, m.p. 180°C (compound 481) and
4-(cis-4-tert.-butylcyclohexylamino)-5-chloro-1-(cyanomethyl)-6- ethylpyrimidinium bromide, m.p. 207°C (compound 482)
C. Biological examples
Use as insecticide/acaricide
Example 1
A Petri dish whose bottom is covered with filter paper and which contains about 5 ml of culture medium is prepared. Pieces of filter paper with about 30, 24-hour-old eggs of the tobacco budworm (Heliothis virescens) are dipped into an aqueous solution of the formulated preparation to be examined for about 5 seconds and subsequently placed into the Petri dish. A further 200 μl of the aqueous solution are spread over the culture medium. The Petri dish is sealed and then kept at about 25°C in a controlled climate chamber. After 6 days storage, the effect of the preparation on the eggs and the larvae which may have hatched from these is determined. At a concentration of 300 ppm (based on the content of active compound), compounds 132,191,199 and 439 caused a mortality of 90-100%.
Example 2
Germinated field bean seeds (Vicia fabae) with radicles are transferred into brown bottles filled with tap water and subsequently populated with approximately 100 black bean aphids (Aphis fabae). Plants and aphids are then dipped for 5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution has run off, plants and animals are stored in a controlled climate chamber (16 hours of light/day, 25"C, 40 - 60% relative atmospheric humidity). After 3 and 6 days storage, the effect of the preparation on the aphids is determined. At a concentration of 300 ppm (based on the content of active compound), compounds 132,191 and199 caused an aphid mortality of 90-100%.
Example 3
The leaves of 12 rice plants having a stem length of 8 cm are dipped for 5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution has run off, the rice plants treated in this manner are placed in a Petri dish and populated with about 20 larvae (L3 stage) of the rice leafhopper species Nilaparvata lugens. The Petri dish is sealed and then stored in a controlled climate
chamber (16 hours of light/day, 25"C, 40 - 60% relative atmospheric humidity). After 6 days storage, the mortality among the leafhopper larvae is determined. At a concentration of 300 ppm (based on the content of active compound), compounds 132,191,199 and 439 caused a mortality of 90-100%.
Example 4
A Petri dish, half of whose bottom is covered with filter paper and contains a germinated maize corn on a moist cotton pad, is prepared. About 50, 4 - 5-day-old eggs of the southern corn rootworm (Diabrotica undecimpunctata) are transferred onto the filter paper. Three drops of 200 μl of an aqueous solution of the formulated preparation to be examined are pipetted onto the eggs, and the rest is pipetted onto the maize corn. The Petri dish is sealed and then stored at about 25"C in a controlled climate chamber. After 6 days storage, the effect of the preparation on the eggs and the larvae which may have hatched from these is determined. At a concentration of 300 ppm (based on the content of active compound), compounds 132 and 199 caused a mortality of 90-100%.
Example 5
Cut stems of bean plants (Phaseolus vulgaήs) carrying one leaf are transferred into brown bottles filled with tap water and subsequently populated with approximately 100 spider mites (Tetranychus urticae). Plant leaf and spider mites are then dipped for
5 seconds into an aqueous solution of the formulated preparation to be examined. After the solution has run off, plants and animals are stored in a controlled climate chamber (16 hours of light/day, 25°C, 40 - 60% relative atmospheric humidity). After
6 days storage, the effect of the preparation on all stages of the spider mites is determined. At a concentration of 300 ppm (based on the content of active compound), compounds 132,191,199 and 439 caused a mortality of 90-100%.
Claims
1. A compound of formula
(1) A is CH and D is N+R or
A is nitrogen and D is N+R or
A is N+R and D is nitrogen, where
R is CR4R5DaR6,
(2) Qn" is an inorganic or organic anion, n being 1 , 2, 3 or 4;
(3) R1 is hydrogen, halogen, (C-|-C8)-alkyl, (C-|-C8)-haloalkyl, (C╬╖-CsJ-alkoxy or
(C3-C6)-cycloalkyl;
(4) R2 and R3 are identical or different and are each hydrogen, (C-|-C8)-alkyl,
(C2-C8)-alkenyl, (Ci-Cβr-alkoxy, halogen, hydroxy, cyano, nitro, thiocyanato, (Cπ-C8)-alkoxycarbonyl, (C-|-C8)-alkylthio,
(C╬╖-C8)-alkylsulfinyl, (C╬╖-CsJ-alkylsulfonyl, amino; (C-|-C8)-alkylamino,
(C-ι-C8)-dialkylamino or (C3-C6)-cycloalkyl, and in which in the alkyl, cycloalkyl, alkenyl, alkynyl groups or the groups derived from them, such as alkoxy, alkylfyl, alkanoyl, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino, a saturated carbon unit can be replaced by a hetero atom unit such as oxygen, S(O)x, where x = 0, 1 or 2 or by dimethylsilyl and further in these groups or derived groups up to 3 hydrogen atoms can be replaced by halogen and in the case of fluorine also all hydrogen atoms can be replaced by fluorine; or R2 and R3 together with the carbon atoms to which they are attached form an unsaturated 5- or 6-membered carbocyclic ring which may, if it is a 5-membered ring, contain an oxygen or sulfur atom instead of CH2, or which may, if it is a 6-membered ring, contain one or two nitrogen atoms instead of one or two CH units, and which may be substituted by 1, 2 or 3 identical or different radicals, these radicals being (C-1-C4)- alkyl, (C-|-C4)-haloalkyl, preferably trifluoromethyl, halogen, (C1-C4)- alkoxy or (Cπ-C4)-haloalkoxy; or
R2 and R3 together with the carbon atoms to which they are attached form a saturated 5-, 6- or 7-membered carbocyclic ring which may contain oxygen and/or sulfur instead of one or two CH2 groups and which may be substituted by 1, 2 or 3 (C-|-C4)-alkyl groups;
(5) X is O, S(O)q where q = 0, 1 or 2, NR7, NR7CO, NR7CS or CR8R9, where R7 is hydrogen and R8 and R9 independently of one another are each hydrogen or (Cπ_C4)-alkyl,
(6) Y - Z together are a (C1-C2╬╕)-hydrocarbon radical which is straight-chain or branched and in which one or more, preferably up to three, CH2 may be replaced by hetero atom radicals such as O, NRl 0, S, SO, SO2 or
SiR 1R12, where R 0 is hydrogen, (C-|-C4)-alkyl or (C«|-C4)-acyl, and
Rη 1 and R12 are identical or different and are each independently of the other (Cπ-C4)-alkyl, phenyl or substituted phenyl, and where this
(Cn-C2o)-hydrocarbon radical with the possible abovementioned variations may be substituted by one or more, preferably up to three, identical or different radicals selected from the group consisting of
(C-i-CyJ-alkyl,
(C2-C4)-alkenyl,
(C2-C4)-alkynyl,
(C3-C7)-cycloalkyl,
(C3-C7)-cycloalkenyl, halogen, halo-(C╬╣-C4)-alkyl, halo-(C-j-C4)-alkoxy, hydroxy and
(Cπ-C4)-acyl; or, if not included in the above definitions,
(7) Y is a bond or a bivalent hydrocarbon chain having 1 to 6 carbon atoms which may be substituted by one or more, preferably up to three, identical or different radicals selected from the group consisting of (Ci-C ϊ-alkyl,
(C2-C4)-alkenyl,
(C3-C7)-alkynyl,
(C3-C7)-cycloalkyl,
(C3-C7)-cycloalkenyl, halogen, halo-(C-|-C4)-alkyl, halo-(Cπ-C4)-alkoxy, hydroxyl and (C-|-C4)-acyl; and
(8) Z is aryl or O-aryl, where aryl is preferably a naphthyl or phenyl group, heterocycyl or heterocyclyloxy, each of which may be substituted by one or more, preferably up to five, in particular up to three, identical or different radicals selected from the group consisting of halogen,
(C3-C8)-cycloalkyl,
(C3-C8)-cycloalkenyl, phenoxy, substituted phenoxy, phenylthio, substituted phenylthio, phenyl, substituted phenyl, optionally substituted heterocyclyl, optionally substituted heterocyclylthio
NO2,
-C(O)-R13, acetoxy, hydroxyl, cyano,
SiRl4Rl5Rl6,
O-SiR1 R15R16, NRl7Rlδ S(O)R19, SO2R19, (Cπ-Ci2)-alkyl, (C2-C-|2)-alkenyl, (C-|-C-|2)-alkoxy and (C-|-C-|2)-alkylthio; and
R13 is (C╬╣-C7)-alkyl, halo-(C -C )-alkyl, (C3-C7)-cycloalkyl, halo-
(C-C7)-cycloalkyl, (C<|-C7)-alkoxy, phenyl or substituted phenyl;
Rl4, R15 and R16 are identical or different and are each independently of one another (C-|-C4)-alkyl, phenyl and/or substituted phenyl;
Rπ 7 and R^8 are identical or different and are each independently of the other hydrogen, (C-|-C4)-alkyl and/or (C-|-C4)-acyl;
R19 is (Cπ-C-|o)-alkyl, phenyl or substituted phenyl; wherein (C-|-C<|2r-alkyl, (Cη-C-|2)-alkoxy, and (C2-Cη2)-alkenyl one or more, preferably up to 3, CH2 groups may be replaced by hetero atom radicals such as O, S, SO, SO2, NR1°' or SiRll'Rl2'; R1°', RH' and R12' have the meanings of R10, R , R12; the (Cπ-C-|2)-alkyl radical with or without the abovementioned variations may also be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group below consisting of halogen, halo-(C-|-C4)-alkoxy, hydroxyl, (C3-C8)- cycloalkyl, (C3-C8)-cycloalkenyl, (C-|-C4)-acyl, phenoxy, substituted phenoxy, phenyl, substituted phenyl, phenylthio and substituted phenylthio; in the (Cπ-C7)-alkoxy and (C-1-C7)- alkylthio radicals, one or more, preferably up to three, CH2 groups may be replaced by O, and these radicals may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of halogen, phenyl, substituted phenyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkenyl, phenoxy and substituted phenoxy; or, if not included in the above definitions,
(9) Y is a bond or a bivalent hydrocarbon chain having 1 to 6 carbon atoms, preferably methylene, which is substituted by one or more, preferably up to three, identical or different radicals selected from the group consisting of
(C-i-C^-alkyl,
(C2-C4)-alkenyl,
(C3-C7)-alkynyl,
(C3-C7)-cycloalkyl,
(10) Z is (C3-C8)-cycloalkyl or (C5-C8)-cycloalkenyl, where a CH2 group of the carbocycle may be replaced by NR20;
R20 is phenyl or substituted phenyl and the (C3~C8)-cycloalkyl or (C5-
C╬▓J-cycloalkenyl radical may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of (C-i-C-is.-alkyl,
(C3-C8)-cycloalkyl, (C3-C8)-cycloalkoxy,
(C2-C18)-alkenyl,
(C2-C18)-alkynyl,
(Cl-Cπ2)-alkoxy,
(C-| -C 12)-alkanoyloxy, formyl, (C2-C12)-acyl,
( -C -j 2)-alkoxycarbonyl,
SiR2 R22R23, NR24R25
C(O)NR2 R25, hydroxyl, halogen, aryl, heteroaryl,
O aryl,
O heteroaryl,
CH2╬╕aryl,
CH2╬╕heteroaryl,
(C-╬╣-Ci8)-alkanediyldioxy,
(C-|-C-|3)-alkoximino and
(C2-C-|8)-alkylidene and where, if not included in the above definitions, one or more, preferably up to three, CH2 groups in the (C-j.Cis)"- (C2-C18)-. (C1.C12)-, (C2-C12)- and (C-|-Ci3)-hydrocarbon radicals mentioned may be replaced by hetero atom radicals such as O, NR10" or SiRl 1"R12 ", these hetero atom radicals preferably not being adjacent to one another, where R10", R11" and R12" have the meanings of R10,
R11 , R12 and where additionally 3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle and where these hydrocarbon radicals with or without these variations may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of hydroxyl, halogen, alkyl, haloalkyl, cycloalkyl, acyl, phenyl, substituted phenyl, optionally substituted heterocyclyl, phenylthio and substituted phenylthio; where heteroaryl may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents; where aryl is as defined under (8); where R24 and R25 are identical or different and are each independently of the other hydrogen, (Cπ-C4)-alkyl, (C-|-C4)-acyl, (C3-
C6)-cycloalkyl, phenyl and substituted phenyl and where R21, R22,
R23 are identical or different and are each independently of the others (C-|-C-|8)-alkyl, (C<|-C"|8)-alkoxy, (C3-C8)-cycloalkyl and aryl, where in the (C-|-C-|8r-hydrocarbon radicals more than one, preferably up to three, non-adjacent CH2 groups may be replaced by oxygen and where
3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle, it also being possible for two of the carbon radicals (for example R21 and
R22) attached to silicon together to form a cycle, the silicon atom in this case being a ring atom of this cycle, and where additionally these (C-|-C-|8)-hydrocarbon radicals with or without the variations may be substituted by one or more (in the case of halogen up to the maximum number) identical or different radicals selected from the group consisting of halogen, haloalkyl, cycloalkyl, where the substituents on the cycloalkyl or cycloalkenyl radicals defined under (10) may be cis or trans with respect to the unit (X-Y) and where, in the case that the cycloalkyl group is the cyclohexyl radical and the abovementioned units are in the 1 ,4 position, preference is given to the cis configuration; or
(11) Y is a bond; and
(12) Z is (a) a group of the formula II
where each X1 independently of the other is sulfur or oxygen; Rz is hydrogen, (C-|-C4)-alkyl, trifluoromethyl or (C-|-C4)-alkoxy; or
Ry is alkyl, alkenyl, alkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals and where in the alkyl, alkenyl or alkynyl radicals mentioned one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O)x, where x = 0, 1 or 2, NR26 or SiR27R28, where R26 is hydrogen, (C-|-C4)-alkyl, (Cπ-C4)-alkoxy or
(C-|-C4)-alkanoyl and R27 and R28 are each (Cπ-C4)-alkyl, preferably methyl; and where additionally 3 to 12 atoms of these hydrocarbon radicals, which may be modified as mentioned above, may form a cycle and where these hydrocarbon radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals selected from the group consisting of halogen, aryl, aryloxy, arylthio, cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, alkanoyl, cycloalkanoyl, haloalkanoyi, aroyl, arylalkanoyl, cycloalkylalkanoyl, heterocyclylalkanoyl, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, cycloalkyl- alkoxycarbonyl, arylalkoxycarbonyl, heterocyclylalkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, alkanoyloxy, haloalkanoyloxy, cycloalkanoyloxy, cycloalkylalkanoyloxy, aroyloxy, arylalkanoyloxy, heterocycloylalkanoyloxy, alkylsulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyanato or nitro, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or where Ry and Rz together form a three- to eight-membered ring system which is spirocyclically linked to the ring system containing the hetero atoms X1 and where one or two CH2 groups, preferably one CH2 group, may be replaced by hetero atom units such as oxygen, S(O)n where n = 0, 1 or 2 or NR29, where R29 is hydrogen, alkyl, alkoxy, alkanoyl, benzoyl, aryl or heteroaryl, where the benzoyl, aryl or heteroaryl radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, and where the ring system formed by Ry and Rz may be unsubstituted or substituted by up to three, but preferably one, substituents and where these substituents are identical or different and are each alkyl, haloalkyl, alkoxy, alkylthio, aryl, aryloxy, arylthio, aralkyl, arylalkoxy, arylalkylthio, cycloalkyl, cycloalkoxy, cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, trialkylsilyl or alkoxycarbonyl, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or where the ring system formed by Ry and Rz, together with a further benzene ring or cyclohexane ring, forms a condensed ring system, preferably the indane, 1,2,3,4-tetrahydronaphthaiene, decalin or benzocycloheptane system, and where the benzene ring in these condensed systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents; in particular those groups of the formula II where
Ry is (C1-C20. -alkyl, (C2-C2o)-alkenyl, (C2-C2o)-alkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals and where in the alkyl, alkenyl or alkynyl radicals mentioned one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O)x, where x = 0, 1 or
2, NR26 or SiR27R28, where R26 is hydrogen, (C╬╣-C4)-alkyl,
(Cπ-C4)-alkoxy or (C-|-C4)-alkanoyl and R27 and R28 are each
(C-|-C4)-alkyl, preferably methyl, and where additionally 3 to 12 atoms of these hydrocarbon radicals, which may be modified as above, may form a cycle and where these hydrocarbon radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of halogen, aryl, aryloxy, arylthio, (C3-C8)- cycloalkoxy, (C3-C8)-cycloalkylthio, heterocyclyl, heterocyclyloxy, heterocyclylthio, (Cι-C-|2)-alkanoyl, (C3-C8)- cycloalkanoyl, (C2-Cπ2)-naloalkanoyl, aroyl, aryl-(C-|-C4)- alkanoyl, (C3-C8)-cycloalkyl-(C-|-C4)-alkanoyl, heterocyclyl-(C«|-
C4)-alkanoyl, (Cι-C«|2)-alkoxycarbonyl, (C<|-Cπ2r- haloalkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C3-C8)- cycloalkyl-(C-|-C4)-alkoxycarbonyl, aryl-(C-|-C4)-alkoxycarbonyl, heterocyclyl-(C-|-C4)-alkoxycarbonyl, aryloxycarbonyl, heterocyclyloxycarbonyl, (C-|-Cπ2)-a'kanoyloxy, (C2-C12)- haloalkanoylalkoxy, (C3-C8)-cycloalkanoyloxy, (C3-C8)- cycloalkyl-(Cι-C4)-alkanoyloxy, aroyloxy, aryl-(C-|-C4)-alkanoyl- oxy, heterocyclyl-(C-|-C4)-alkanoyloxy, (Cπ-Cπ2)-alkyl- sulfonyloxy, arylsulfonyloxy, hydroxyl, cyano, thiocyanato or nitro, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or where Ry and Rz together form a three- to eight-membered ring system, which is spirocyclically linked to the ring system containing the hetero atoms χ1 and where one or two CH2 groups, preferably one CH2 group, may be replaced by hetero atom units such as oxygen, S(O)n where n = 0, 1 or 2 or NR29, where R29 is hydrogen, (Cπ-C8)-alkyl, (Cπ-C8.-alkoxy, (C-i-Cβ)- alkanoyl, benzoyl, aryl or heteroaryl, where the benzoyl, aryl or heteroaryl radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents and where the ring system formed by Ry and Rz may be unsubstituted or substituted by up to three, but preferably one, substituents and where these substituents are identical or different and are each (Cη-Cβ)- alkyl, (C-|-C8)-haloalkyl, (Cπ-C8)-alkoxy, (C-|-C8)-alkylthio, (C3- Cβr-cycloaikyl, (C3-C8)-cycloalkoxy, (C3-C8)-cycloalkylthio, aryl, aryloxy, arylthio, aryl-(Cπ-C4)-alkyl, aryl-(C1-C4)-alkoxy, aryl- (C-|-C4)-alkylthio, heterocycyl, heterocyclyloxy, heterocyclylthio, (C-|-C8)-trialkylsilyl, preferably (Cη-Cβr-alkyldimethylsilyl, or (C-|-C8)-alkoxycarbonyl, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or where the ring system formed by Ry and Rz, together with a further benzene ring or cyclohexane ring, forms a condensed ring system, preferably the indane, 1 ,2,3,4-tetrahydro- naphthalene, decahydronaphthalene or benzocycloheptane system and where the benzene ring in these condensed systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, where among the compounds where the carbon atom between the hetero atoms X1 carries only the substituent Ry, the substituents X and Ry are preferably cis to each other; Rz is hydrogen, (C-|-C4)-alkyl, trifluoromethyl or (C-|-C4)-alkoxy; or (b) a group of formula
where ╬│1, Y2 and Y3 independently of one another are each a group of the formula -O-, -CO-, -CNR30-, -S(O)r where r = 0, 1 or 2,
-N(O)|R30- where I = 0 or 1 or a group of the formula CR31R32; or ╬│1 or Y3 stands in place of a direct bond, where
R30 JS hydrogen, (Cπ-C4)-alkyl, (Cη-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkynyl, (Cπ- C4)-alkoxy, (C1-C4)-haloalkoxy, (C-|-C4)-alkylthio, (Cπ-C4)-halo- alkylthio, (Cπ-C4)-alkanoyl, (C2-C4)-haloalkanoyl, (C3-C5)- cycloalkyl, (C-|-C4)-alkylsulfonyl, (C-|-C4)-haloalkylsulfonyl, (C-|-C4)-alkoxy-(C-|-C4)-alkyl, (C-|-C4)-alkoxycarbonyl;
R 1 and R32 independently of the other are each hydrogen, hydroxyl, halogen, cyano, (C-|-C4)-alkyl, (C-j-C^-haloalkyl, (C2-C4)- alkenyl, (C2-C4)-haloalkenyl, (C2-C4)-alkynyl, (C2-C4)- haloalkenyl, (C3-C5)-cycloalkyl, (C-(-C4)-alkanoyl, (C1-C4)- haloalkanoyl, (C-|-C4)-alkoxy, (C-|-C4)-haloalkoxy, (C-1-C4)- alkylthio or (Cπ-C4)-haloalkylthio; m is 0, 1, 2, 3 or 4, preferably 1 or 2; n is 0, 1, 2, 3 or 4, preferably 1 or 2; Z1 is a direct bond, NR33, O, S(O)s where s = 0, 1 or 2, OSO2,
SO2O, NR34SO2, SO2NR35, SiR36R37 or U-C(W)-V, where R36 ancj R37 are each (C-|-C4)-alkyl or phenyl, preferably methyl;
U is a direct bond, NR38 or O;
W is oxygen or sulfur, preferably oxygen;
V is a direct bond, NR39 or oxygen, where R33 R34 R35t R38 and R39 are identical or different and are each hydrogen, alkyl, alkoxy, alkanoyl or cycloalkyl;
R┬░. are substituents which are independent of one another and each is halogen, cyano, nitro, (C<|-C2o)-alkyl, (C2-C2o)-alkenyl,
(C2-C2o)-alkynyl, (C3-C8)-cycloalkyl, (C4-C8)-cycloalkenyl, where in the last 5 radicals one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O)x where x = 0, 1 or 2, NR40 or SiR 1R42 and where these last 5 radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D1R43, or
R┬░. is aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D2R44, or two adjacent radicals zl-R0. may combine with the carbon atoms to which they are attached to form a fused cycle having 4 to 6 ring atoms which is carbocyclic or contains hetero ring atoms selected from the group consisting of O, S and N and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C-|-C4)-alkyl and oxo, or
R33 R35 or R39 independently of one another may combine with the
R┬░. located at Z to form a 4- to 8-membered ring system in which one or two CH2 groups, preferably one CH2 group, may be replaced by hetero atom units such as oxygen, S(O)t where t =
0, 1 or 2 or NR45, where
R40 is hydrogen, (C-|-C4)-alkyl, (Cπ-C4)-alkoxy or (C-|-C4.-alkanoyl;
R41 and R42 independently of the other are each (Cπ-C4)-alkyl, preferably methyl; D1 and D2 are independent of each other and each is a direct bond, oxygen, S(O)k, SO2O, OSO2, CO, OCO, COO, NR46,
SO2NR46, NR 6SO2, ONR46, NR46O, NR 6CO, CONR46 or
SJR47R48I and k = 0, 1 or 2, where R46 independently of the others is hydrogen, (C-|-C4)-alkyl, (C1-C4)- alkanoyl or (C3-C5)-cycloalkyl;
R47 and R48 independently of the other are each (C-|-C4)-alkyl;
R43 and R44 independently of the other are each hydrogen, cyano, nitro, halogen, (Cπ-C8)-alkyl, (C-j-CsJ-haloalkyl, (C2-C8)- alkenyl, (C2-C8)-haloalkenyl, (C^-CsJ-alkynyl, (C2-C8)- haloalkynyl, (C-|-C8)-alkoxy-(C-|-C4)-alkyl, (Ci-CsJ-haloalkoxy- (C1-C4)-alkyl, (C-|-C8)- haloalkylthio-(C-|-C4)-alkyl, (C3-C8)-cycloalkyl, (C4-C8)- cycloalkenyl, (C3-C8)-cycloalkyl-(C-|-C4)-alkyl, (C4-C8)- cycloalkenyl-(C-|-C4)-alkyl, aryl, heterocyclyl, aryl-(C-|-C4)-alkyl or heterocyclyl-(C-|-C4)-alkyl, where in the last 8 radicals the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R49, or
R43 and R44 located at the same carbon atom together are an oxo group, where
R49 is (C1-C4)-alkyl, (Cη^.-haloalkyl, (C1-C )-alkoxy, (C-1-C4)- haloalkoxy, cyano, nitro or halogen; R45 js hydrogen, (Cπ-C8)-alkyl, (C-|-C4)-haloalkyl, (Cπ-C4)-alkoxy,
(Cπ-C4)-alkylthio, (C3-C5)-cycloalkyl, (C2-C4)-alkenyl, (C2-C4)- alkynyl, (C<|-C4)-alkanoyl, (C2-C4)-haloalkanoyl, (C2-C4)- alkoxyalkyl, phenyl-(C-j-C4)-alkyl or phenyl where the phenyl groups may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R50, where
R50 is (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C-|-C4)-alkoxy, (C-j-C4)- alkylthio, halogen or cyano; or, if not included in the above definitions,
(c) is a group of the formula IV
Y4 is a direct bond or CH2;
Z2 is oxygen, NR51, S(O)m where m = 0, 1 or 2;
RU and wl-R* are substituents of the heteroaliphatic ring system, where
Ru is hydrogen, halogen, cyano, (C«|-C4)-alkyl, (Cη-C4)-haloalkyl,
(C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C2-C4)-alkynyl, (C2-C4)- haloalkynyl, (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C1-C4)- alkoxy, (C«|-C4)-haloalkoxy, (Cπ-C4)-alkanoyloxy, (C1-C4)- haloalkanoyloxy, (Cπ-C4)-alkylthio or (C-|-C4)-haloalkylthio;
W is a direct bond, oxygen, -NR52-, -CO-, -COO-, CONR52-, sulfur, -C=N-, -C=N-O- or -NR52O-;
R* is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, where in the last 5 radicals one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O)x where x = 0, 1 or 2, NR53 or SiR54R55, and where these last 5 radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D3R56, or
R* may be aryl or heterocyclyl, where both of these radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D R57 or
Ru and R* together form a three- to eight-membered ring system which is spirocyclically linked to the ring system containing the hetero atoms Y4 and Z2 and in which one or two CH2 groups, preferably one CH2 group, may be replaced by hetero atom units such as oxygen, S(O)n where n = 0, 1 or 2, or NR58, where
R51 is hydrogen, (Cπ-C4)-alkyl, (C-|-C4)-haloalkyl, (C2-C4)-alkenyl,
(C2-C4)-haloalkenyl, (C2-C4)-alkynyl, (C2-C4)-haloalkynyI, (C-j-
C4)-alkoxy, (C-|-C4)-alkanoyl, (C2-C4)-haloalkanoyl, (C1-C4)- alkoxy- (C1-C4)-alkyl, (C1-C4)-alkylthio-(C1-C4)-alkyl, (C-1-C4)- alkoxycarbonyl, (C╬╖-C4)-alkylsulfonyl, (C<|-C4)-haloalkylsulfonyl, phenylcarbonyl, phenyl-(C-|-C4)-alkyl or phenyl, where the last 3 radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R59, or
R5 is CONR60R61 where
R6┬░ and R61 independently of the other are each hydrogen, (C1-C4)- alkyl or phenyl, where the phenyl group may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R62, and R62 and R59 independently of the other are each (C<|-
C4)-haloalkyl, (C-|-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)- alkylthio or halogen; R52 is hydrogen, (Cπ-C4)-alkyl, (C<|-C4.-alkanoyl or (C3-C5)-cycloalkyl; Rδ3 is hydrogen, (C-|-C4)-alkyl, (C-|-C4)-alkoxy or (C-|-C4)-alkanoyl;
R54 and R55 independently of the other are (Cπ-C4)-alkyl, preferably methyl;
R58 is hydrogen, alkyl, alkanoyl, alkoxy, benzoyl, aryl or heteroaryl, where the last 3 radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R63;
R63 may be (C-|-C4)-alkyl, (C╬╖-C4)-haloalkyl, (C╬╖-C4)-alkoxy, (C1-C4)- haloalkoxy, cyano, nitro or halogen, and the ring system formed by Ru and R* may be unsubstituted or substituted by up to three, but preferably one, substituents D5R64, or the ring system formed by Ru and R*, together with a further benzene ring or cyclohexane ring, forms a condensed ring system, preferably the indane, 1 ,2,3,4-tetrahydronaphthalene, decalin or benzocycloheptane system, and the benzene ring in these condensed systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents D^R^5, where
D3, D4, D5 and D^ are independent of one another and are each a direct bond, oxygen, S(O)k, SO2O, OSO2, CO, OCO, COO,
SO2NR66, NR66SO2, NR66O, ONR66, NR66, NR66CO,
CONR66 or SiR67R68, where k = 0, 1 or 2; and R56 R57 R64 ancj R65 independently of one another are each hydrogen, cyano, nitro, halogen, (Cπ-C8)-alkyl, (C-i-Cβ)- haloalkyl, (C2-C8)-alkenyl, (C2-C8)-haloalkenyl, (C2-C8)-alkynyl, (C2-C8)-haloalkynyl, (Cπ-C8)-alkoxy-(Cπ-C4)-alkyl, (C-|-Cs)- haloalkoxy-(C-|-C4)-alkyl, (C-|-C8)-alkylthio-(C-|-C4)-alkyl, (Cι-C8)-haloalkylthio-(C-|-C4)-alkyl, (C3-C8)-cycloalkyl, (C4- C8)-cycloalkenyl, (C3-C8)-cycloalkyl-(Cπ-C4)-alkyl, (C4-C8)- cycloalkenyl-(C-|-C4)-alkyl, aryl, heterocyclyl, aryl-(C-|-C4)-alkyl or heterocyclyl-(C1-C4)-alkyl, where in the last 8 radicals the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R69, where R66 independently of the others is hydrogen, (C-j-C4)-alkyl, (C1-C4)- alkanoyl or (C3-C5)-cycloalkyl and R67 and R68 independently of the other are each (Cπ-C4)-alkyl, and
R69 independently of the others may be (Cπ-C4)-alkyl, (C1-C4)- haloalkyl, (C-|-C4)-haloalkoxy, cyano, nitro, halogen, (Cπ-C4)-alkanoyl or (C2-C4)-haloalkanoyl, or two of the radicals
R56 R57 R64 R65_ R69 w ich are located at the same carbon atom together, and in each case independently of the others, are an oxo group; in particular those groups of the formula IV where
R* is hydrogen, (C-j-Cer-alkyl, (C2-C8)-alkenyl, (Oj-CsJ-alkynyl, (C3-
C8)-cycloalkyl or (C4-C8)-cycloalkenyl and where in the last 5 radicals one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by a carbonyl group or by hetero atom units such as oxygen, S(O)x where x = 0, 1 or 2,
NR53 or SiR54R55, and where these last 5 radicals with or without the variations mentioned may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D3R5^, or
R* may be aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D4R57, or
Ru and R* together form a five- or six-membered ring system which is linked, preferably spirocyclically, to the ring system containing the hetero atoms Y4 and Z2, and in which one CH2 group may be replaced by hetero atom units such as oxygen, S(O)n where n = 0, 1 or 2 or NR58, where R53 is hydrogen, (Cπ-C4)-alkyl, (Cπ-C4)-alkoxy or (C-|-C4)-alkanoyl and R54 and R55 independently of the other are (Cπ-C4)-alkyl, preferably methyl;
R58 is hydrogen, (C╬╣-Cg)-alkyl, (C╬╖-C╬▓J-alkanoyl, benzoyl, aryl or heteroaryl, where the last 3 radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R^3╬╣ and
R63 may be (C-|-C4)-alkyl, (C-|-C4)-haloalkyl, (C<|-C4)-alkoxy,
(Cπ-C4)-haloalkoxy, cyano, nitro or halogen, and the ring system formed by Ru and R* may be unsubstituted or substituted by up to three, but preferably one, substituents Q5R64 or tne πng system formed by Ru and R*, together with a further benzene ring or cyclohexane ring, forms a condensed ring system, preferably the indane, 1,2,3,4-tetrahydro- naphthalene, decalin or benzocycloheptane system, and the benzene ring in these condensed systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents D^R^ , where in the compounds where the carbon atom between Y4 and Z2 where Y = CH2 only carries the substituent W^R*, the substituents X and W1-R* are cis to each other;
D3, D4, D5 and D^ are independent of one another and are each a direct bond, oxygen, S(O)|<, SO2O, OSO2, CO, OCO, COO,
SO2NR66, NR66SO2, NR66O, ONR66, NR66, NR66CO or CONR66, and k = 0, 1 or 2, R66 independently of the others is hydrogen, (C╬╣-C4)-alkyl, (C1-C4)- alkanoyl or (C3-C5)-cycloalkyl and
R56 R57 R64 and R65 independently of one another are each hydrogen, cyano, nitro, halogen, preferably fluorine, (C-j-Ce)- alkyl, (C3-C8)-cycloalkyl, aryl, heterocyclyl, where in the last 3 radicals the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R69, where R69 independently of the others may be (C-j-C4)-alkyl, (C1-C4)- haloalkyl, (C-|-C4)-haloalkoxy, cyano, nitro, halogen, or two of the radicals R56 R57f R64 R65 R69 w jch are located at the same carbon atom, together and in each case independently of the others, are an oxo group;
(14) R4 is a) hydrogen, halogen or C<|_4-alkyl or
(b) a negative charge, which can represent Qn_
(15) R5 is hydrogen, halogen, CN, nitro, (C<|-C4)-alkoxycarbonyl, (C-1-C4)- alkylcarbamoyl, di-(C<|-C4)-alkylcarbamoyl, (C-|-C8)-alkoxy, (C╬╖-C╬▓)- alkyl, (C2-C8)-alkenyl, aryl or (C3-C8)-cycloalkyl;
(15) Da is c) a direct bond, NR70, N(O)R70, O, S, SO, SO2, C(=Wa), OC(=Wa) or d) Ua(C=Wa)Va (Ua and Va are a direct bond, NR70, S or O, except Va is not a bond when Ua is bond or O), SiR72R73, Ub(P=Wb)V Vc, Ub(SO2)Uc (one of Ub and Uc is a direct bond, NR70, S or O and the other is NR70), Ua(CWa)(CWa)Vb, NR70O, O NR70, NR70 NR70,
N=N, -N=, - NR70-N= or-O-N= , and
Wa is O, S or NR71;
Wb is O or S;
Ua, Vb and Vc, independently of each other are a direct bond, NR70, S or O each R70, which may be the same or different from any other R70, is hydrogen, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted amino, optionally substituted acyloxy, and may also form a 4 to 8 membered with R6,
R112 or R113, respectively with the Da, D12 or. D13 to which they are attached, and in the case Da is UbP(=Wb)VbVc, the two R6 groups together with the VbPVc, to which they are attached can form a 4 to 8 membered ring
each R71 , which may be the same or different from any other R71 , is hydrogen, nitro, cyano, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted amino or optionally substituted acyloxy;
R72 and R73 are alkyl or optionally substituted aryl;
(16) R6 is hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, in which up to three CH2 units in a carbon containing group can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO2, NR70 or Si R72R73 and can also be substituted by nitro, halogen, SF5 or D12R1 12, and in the case Da is UbP(=W )VbVc, the two R6 groups together with the VbPVc, to which they are attached can form a 4 to 8 membered ring
D12 is e) a direct bond, NR70, N(O)R70, O, S, SO, SiR72R73, U'(CW)V, or f) U '(PW1')V1'V2', U2'(SO2)U3'I Si(OR72)R73, Si(OR72)(OR73),NR70O,
ONR70, NR 0NR70, N=N, =N-, =N-NR70- =N-O-, -N=, -NR70-N= or - O-N= and
U'.U1' V, V1' and V2', independently of each other are a direct bond,
NR70 S or O
W' is O, S or NR71;
W' is O or S;
U2' and U3', independently of each other are a direct bond, NR70 or O;
(g) R1 12 is hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, in which up to CH2 units in a carbon containing group can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO2, NR70 or SiR72R73 and can also be substituted by nitro, halogen, SF5 or Dl 3Rπ π 3 and in which two adjacent Dη2Rπ l 2 together with the carbons to which they are attached can form a condensed ring comprising 4 to 6 ring atoms which can be substituted one or more halogen or C-|-C4-alkyl; or
(h) R 12 is a negative charge for D 2 = (CO)O, (SO2)O, U1'(PW )V1O which replaces the ion Qn_; or R1 12 is hydrogen for D12 = O(CO)NH,
NR 0(CO)NH, O(CS)NH, NR70(CS)NH, (CO)NH, (CS)NH, O(CO),
NR 0(CO), SO2NH;
D13 has the same meaning as D12 and R1 13 has the same meaning as Rl12; and in paragaraphs (13) - (16), aryl is as defined under (8) and, if it is not encompassed by the definition the carbon containing groups named under (13) to (16) can be substituted by one or more, preferably up to three (in the case of halogen up to the maximim number) of the same or different groups selected from halogen, cycloalkyl, phenoxy, substituted phenoxy, phenyl or substituted phenyl, with the proviso that at least one of the parameters defined in 13b, 15d or 16f or 16h applies.
2. A compound of the formula I as claimed in claim 1 , in which
A is CH and D is N+R or
A is nitrogen and D is N+R;
Qn_ is an anion such as Hal-, NO3", BF4', BPh4" or PFρ";
R1 is hydrogen, methyl, fluorine or chlorine;
R2 and R3 are each hydrogen, (C«|-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, amino, (Cη-C4)-alkylamino, (C-|-C4)-dialkylamino, trimethylsilylethynyl, methoxycarbonyl, (C<|-C4)-haloalkyl, (C2-C4)-haloalkenyl, methoxy, ethoxy, halogen, methoxymethyl or cyano; or
R2 and R3 join with the linking carbon atoms to form an unsaturated 5- or 6- membered ring with or without substitution which may, in the case of the 5- membered ring, contain a sulfur atom instead of a CH2 unit; or R2 and R3 join with the linking carbon atoms to form a saturated 5- or 6-membered ring which may contain a sulfur or oxygen atom instead of a CH2 unit;
X is NH or oxygen.
3. A compound as claimed in claim 1 or 2, in which
Y is a bond or a methylene group which is substituted by one or two, preferably by one, (C1-C4)-alkyl radical; and
Z is (C3-C8)-cycloalkyl or (C5-C8)-cycloalkenyl, where a CH2 group of the carbocycle may be replaced by NR20;
R20 is phenyl or substituted phenyl and the (C3-C8)-cycloalkyl or (C5-C8)- cycloalkenyl radical may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of (C-i-C-i╬▓J-alkyl,
(C3-C8)-cycloalkyl,
(C3-C8)-cycloalkoxy,
(C2-C18)-alkenyl,
(C2-C18)-alkynyl,
(Cπ-Cπ2)-alkoxy,
(Cl-C<i2)-alkanoyloxy, formyl, (C2-C12)-acyl,
(Cπ-C-|2)-alkoxycarbonyl,
SiR2lR22R23 NR24R25I
CO-NR2 R25, hydroxyl, halogen, aryl, heteroaryl,
O aryl,
O heteroaryl,
CH2╬╕aryl, C^Oheteroaryl,
(C╬╣-Ci8)-alkanediyldioxy,
(C╬╣-Ci3)-alkyl-oximino and
(C2-Cπ8)-alkylidene and where, if not included in the above definitions, one or more, preferably up to three, CH2 groups in the (C-j-C-iβ)-.
(C2-C-18)-. (C1-C-12)-. (C2-C-12)- and (Ci-C^-hydrocarbon radicals mentioned may be replaced by hetero atom radicals such as O, NRπ " or
SiR11 "R12", these hetero atom radicals preferably not being adjacent to one another, where R 0", R1 " and R12" have the meanings of R10, R11, R 2 and where additionally 3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle and where these hydrocarbon radicals with or without these variations may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of hydroxyl, halogen, alkyl, haloalkyl, cycloalkyl, acyl, phenyl, substituted phenyl, phenylthio and substituted phenylthio;
where heteroaryl is unsubstituted or may be substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents; where aryl is as defined under (8); where R24 and R25 are identical or different and are each independently of the other hydrogen, (C-|-C4)-alkyl, (C-|-C4)-acyl, (C3-Cg)-cycloalkyl, phenyl and substituted phenyl and where R2π, R22, R23 are identical or different and are each independently of the others (C-j-C-iβ.-alkyl, (C<|-Ci8)-alkoxy, (C3-
CβJ-cycloalkyl and aryl, where in the (Cη-C-isJ-hydrocarbon radicals more than one, preferably up to three, CH2 groups may be replaced by oxygen and where 3 to 6 carbon atoms of these hydrocarbon radicals may form a cycle, it also being possible for two of the carbon radicals (for example R2"1 and R22) attached to silicon together to form a cycle, the silicon atom possibly being part of this cycle, and where additionally these (Ci-C«|8)-hydrocarbon radicals with or without the variations may be substituted by one or more (in the case of halogen up to the maximum number) identical or different radicals selected from the group consisting of halogen, haloalkyl, cycloalkyl, where the substituents on the (C3-C8)-cycloalkyl or (Cs-CβJ-cycloalkenyl radicals defined above may be cis or trans with respect to the unit (X-Y) and where, in the case that the cycloalkyl group is the cyclohexyl radical and the abovementioned units are in the 1 ,4 position, preference is given to the cis configuration; or
is a bond; and
(a) is a group of the formula II
where χ1 is oxygen;
Ry is (C1-C2o)-alkyl, (C2-C2θ)-alkenyl, (C2-C2θ)-alkynyl, aryl or heterocyclyl, where the aryl or heterocyclyl radicals mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals and where in the alkyl, alkenyl or alkynyl radicals mentioned one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by hetero atom units such as oxygen or SiR27R28, where R27 and R28 are each (C-|-C4)-alkyl, preferably methyl, and where additionally 3 to 6 atoms of these hydrocarbon radicals, which may be modified as above, may form a cycle, and where these hydrocarbon radicals with or without the variations mentioned may be substituted by one or more, preferably by up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of halogen, preferably fluorine, aryl, aryloxy, arylthio, (C3-C8)-cycloalkoxy, (C3-C8)-cycloalkylthio, heterocyclyl, heterocyclyloxy or (Cπ-C2)-alkoxycarbonyl, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or Ry and Rz together form a five- or six-membered ring system which is linked, preferably spirocyclically, to the ring system containing the hetero atoms X1, and where one CH2 group may be replaced by hetero atom units such as oxygen, S(O)n where n = 0, 1 or 2 or NR29, where R29 is hydrogen, (C-|-C8)-alkyl, (Cπ-C8)-alkanoyl, benzoyl, aryl or heteroaryl, where the benzoyl, aryl or heteroaryl radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, and where the ring system formed by Ry and Rz may be unsubstituted or substituted by up to three, but preferably one, substituents and where these substituents are identical or different and are each (C-j-CsJ-alkyl, (C3- C8)-cycloalkyl, aryl or aryl-(C-|-C4)-alkyl, where the cycloaliphatic, aromatic or heterocyclic ring systems among the substituents just mentioned may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, or where the ring system formed by Ry and Rz, together with a further benzene ring or cyclohexane ring, forms a condensed ring system, preferably the indane, 1,2,3,4-tetrahydronaphthalene, decalin or benzocycloheptane system, and where the benzene ring in these condensed systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents, where in the compounds where the carbon atom between the hetero atoms X1 only carries the substituent Ry, the substituents X and Ry on the heteroaliphatic six-membered ring are preferably cis to each other; and
Rz is hydrogen or (b) is a group of the formula (III)
where Y1 , Y2 and Y3 are each a group of the formula -O-, -S(O)r, where r = 0, 1 or 2 or is a group of the formula CR31 R32 , or Y1 or Y3 stand in place of a direct bond, where
R3*! and R32 independently of the other are each hydrogen or methyl; m1 is 1 or 2; n1 is 1 or 2;
Z is a direct bond, NR33, O, S(O)s where s = 0, 1 or 2, OSO2, SO2O,
NR34SO2, SO2NR35, SiR36R37 or U-C(W)-V, where
U is a direct bond, NR38 or O;
W is oxygen;
V is a direct bond, NR39 or oxygen; and
R36 and R37 are each (C-|-C4)-alkyl or phenyl, preferably methyl;
R33 R34 R35 R38 and R39 are identical or different and are each hydrogen, (C-|-C4)-alkyl, (C-|-C4)-alkoxy, (Cπ-C4)-alkanoyl or (C3-C5)-cycloalkyl;
R┬░. independently of the others is (C -CsJ-alkyl where one or more, preferably up to three, nonadjacent saturated carbon units may be replaced by oxygen and which, with or without the variations mentioned, may be substituted by one or more, preferably up to three (in the case of fluorine up to the maximum number), identical or different radicals D^ R43, or
R┬░. may be aryl or heterocyclyl, where these two radicals may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different radicals D2R44;
D1 and D2 are independent of one another and are each a direct bond, -O-,
-S(O)k-, -SO2O-, -OSO2-, -CO-, -OCO-, -COO-, -NR46-, -SO2NR46-,
-NR 6SO2-, -ONR46-, -NR 6O-, -NR46CO-, -CONR46-, and k = 0, 1 or 2, and where R46 independently of the others is hydrogen, (Cπ-C4)-alkyl, (C1-C4)- alkanoyl or (C3-C5)-cycloalkyl; R43 and R44 independently of the other are each hydrogen, halogen, preferably fluorine, (Cπ-C8)-alkyl, (C3-C8)-cycloaIkyl, aryl or heterocyclyl, where in the last 3 radicals the cycloaliphatic, aromatic or heterocyclic ring systems may be unsubstituted or substituted by up to three (in the case of fluorine up to the maximum number) identical or different substituents R49, where R49 independently of the others may be (Cπ-C4)-alkyl, (C-|-C4)-haloalkyl,
(C-|-C4)-alkoxy, (C-|-C4)-haloalkoxy, cyano, nitro, halogen; or,
(c) is a group of the formula IV
Y4 is a direct bond or CH2;
Z2 is oxygen;
Ru is hydrogen, (Cπ-C4)-alkyl, trifluoromethyl or (C-|-C4)-alkoxy;
W1 is a direct bond, oxygen, -CO-, -COO-, CONR52, sulfur, -C=N-,
-C=N-O- where R52 is hydrogen, (Cπ-C4)-alkyl, (Cπ-C4)-alkanoyl and (C3-C5)-cycloalkyl, and
Rl is as defined above under (12 c).
4. A compound as claimed in any of the preceding claims, in which
R^ is hydrogen;
R2 and R3 are each hydrogen, methyl, ethyl, propyl, methoxy, (C2-C3)-alkenyl, amino, (C<|-C4)-alkylamino, (Cπ-C4)-dialkylamino, (C2-C3)-chloro- or - fluoroalkenyl, (C2-C3)-alkynyl, trimethylsilylethynyl, (Cπ-C3)-chloro- or - fluoroalkyl, methoxymethyl, halogen or cyano; or R2 and R3 together with the ring system to which they are attached form the quinazoline or quinoline system, which may be fluorine-substituted in the carbocyclic moiety; or
R2 and R3 together with the carbon atoms to which they are attached form a saturated 6-membered ring, which may contain an oxygen or sulfur atom instead of a CH2 group.
5. A compound as claimed in any of the preceding claims, in which
X is NH;
Y is a bond; and
Z (a) is cyclopentyl or cyclohexyl, where both radicals may be substituted as above under (10) and where, in the case of cyclohexyl, 1 ,4-substitution is preferred, the substituents being cis to one another; or
( ) is a group of the formula
where
Y1 is CH2;
Y2 is CH2;
Y3 is CH2, O or a direct bond; 1 1 C
ml is 1 or
(d) is a group of the formula IV
where
Y4 is a direct bond or CH2;
Z2 is oxygen;
Ru is hydrogen or methyl.
6. A compound as claimed in any of the preceding claims, in which
A is CH and D is N+R or
A is nitrogen and D is N+R;
Q" is an inorganic or organic anion, such as Hal", NO3", BF4", BPr.4-, PF╬▓";
R5 is hydrogen;
R6 is hydrogen, halogen, (C-|-Cs)-alkyl, (C-j-CsJ-haloalkyl, (C2-C8)-alkenyl, (C2- C8)-alkynyl;
7. A compound as claimed in any of the preceding claims, in which R1 is hydrogen;
R2 is ethyl or methoxymethyl;
R3 is chlorine, bromine or methoxy, preferably those for which R2 is ethyl and R3 is chlorine;
R5 is hydrogen;
R6 is hydrogen or methyl.
8. An insecticidal or acaricidal composition comprising an effective amount of at least one compound as claimed in any one of the preceding claims together with the additives or auxiliaries which are customary for these applications.
9. A method of controlling insects or acarids, which comprises applying an effective amount of a compound as claimed in any in any one of the preceding claims to insects acarids or their loci.
10. Seed, treated or coated with an effective amount of a compound as claimed in in claim 1.
11. Seed, treated or coated with in effective amount of a composition as claimed in claim 8.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU40375/99A AU4037599A (en) | 1998-05-20 | 1999-05-06 | Substituted nitrogen heterocycles and their use as pesticides |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9810860.8 | 1998-05-20 | ||
GBGB9810860.8A GB9810860D0 (en) | 1998-05-20 | 1998-05-20 | Substituted pyridine and pyrimidines, processes for their preparation and their use as pesticides |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1999059978A1 true WO1999059978A1 (en) | 1999-11-25 |
Family
ID=10832407
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1999/003092 WO1999059978A1 (en) | 1998-05-20 | 1999-05-06 | Substituted nitrogen heterocycles and their use as pesticides |
Country Status (3)
Country | Link |
---|---|
AU (1) | AU4037599A (en) |
GB (1) | GB9810860D0 (en) |
WO (1) | WO1999059978A1 (en) |
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Also Published As
Publication number | Publication date |
---|---|
GB9810860D0 (en) | 1998-07-22 |
AU4037599A (en) | 1999-12-06 |
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