MXPA00011410A - Sulfonyl amino (thio)carbonyl triazoline (thi)ons having alkenyl substituents - Google Patents
Sulfonyl amino (thio)carbonyl triazoline (thi)ons having alkenyl substituentsInfo
- Publication number
- MXPA00011410A MXPA00011410A MXPA/A/2000/011410A MXPA00011410A MXPA00011410A MX PA00011410 A MXPA00011410 A MX PA00011410A MX PA00011410 A MXPA00011410 A MX PA00011410A MX PA00011410 A MXPA00011410 A MX PA00011410A
- Authority
- MX
- Mexico
- Prior art keywords
- carbon atoms
- fluorine
- alkyl
- chlorine
- optionally substituted
- Prior art date
Links
- BOXGRONENWXPJP-UHFFFAOYSA-N S(=O)(=O)=C1N(N=NC1)C(=O)SN Chemical compound S(=O)(=O)=C1N(N=NC1)C(=O)SN BOXGRONENWXPJP-UHFFFAOYSA-N 0.000 title abstract 2
- 125000000217 alkyl group Chemical class 0.000 claims abstract description 76
- 150000001875 compounds Chemical class 0.000 claims abstract description 74
- 125000003545 alkoxy group Chemical class 0.000 claims abstract description 60
- 239000001257 hydrogen Substances 0.000 claims abstract description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 44
- 125000003342 alkenyl group Chemical class 0.000 claims abstract description 19
- 125000000753 cycloalkyl group Chemical class 0.000 claims abstract description 18
- 125000000304 alkynyl group Chemical class 0.000 claims abstract description 15
- 125000003282 alkyl amino group Chemical class 0.000 claims abstract description 13
- 125000003302 alkenyloxy group Chemical class 0.000 claims abstract description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052717 sulfur Chemical group 0.000 claims abstract description 12
- 239000011593 sulfur Chemical group 0.000 claims abstract description 12
- 239000011780 sodium chloride Substances 0.000 claims abstract description 11
- 230000002363 herbicidal Effects 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 239000001301 oxygen Substances 0.000 claims abstract description 10
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 125000003710 aryl alkyl group Chemical class 0.000 claims abstract description 8
- 230000000855 fungicidal Effects 0.000 claims abstract description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 8
- 239000004009 herbicide Substances 0.000 claims abstract description 7
- 125000001316 cycloalkyl alkyl group Chemical class 0.000 claims abstract description 6
- 239000000417 fungicide Substances 0.000 claims abstract description 6
- 125000005418 aryl aryl group Chemical class 0.000 claims abstract description 4
- 125000006310 cycloalkyl amino group Chemical class 0.000 claims abstract description 4
- 125000001072 heteroaryl group Chemical class 0.000 claims abstract description 4
- 125000005236 alkanoylamino group Chemical class 0.000 claims abstract description 3
- 125000004663 dialkyl amino group Chemical class 0.000 claims abstract description 3
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims abstract description 3
- 125000005017 substituted alkenyl group Chemical group 0.000 claims abstract 2
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 317
- 239000000460 chlorine Chemical group 0.000 claims description 117
- 229910052801 chlorine Inorganic materials 0.000 claims description 117
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 117
- 239000011737 fluorine Substances 0.000 claims description 116
- 229910052731 fluorine Inorganic materials 0.000 claims description 116
- -1 cyano, carboxy, carbamoyl Chemical group 0.000 claims description 93
- 125000001153 fluoro group Chemical group F* 0.000 claims description 78
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 69
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 69
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 41
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 38
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 38
- 241000196324 Embryophyta Species 0.000 claims description 35
- 150000002431 hydrogen Chemical group 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 32
- 238000002360 preparation method Methods 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 31
- 125000004414 alkyl thio group Chemical group 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical group 0.000 claims description 19
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 18
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000003085 diluting agent Substances 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000004429 atoms Chemical group 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- XLIUPWCZVUDHFH-UHFFFAOYSA-N S(=O)(=O)=NSC(=O)N1N=NCC1 Chemical compound S(=O)(=O)=NSC(=O)N1N=NCC1 XLIUPWCZVUDHFH-UHFFFAOYSA-N 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- ZOAMZFNAPHWBEN-UHFFFAOYSA-N 2-$l^{1}-oxidanylpropane Chemical group CC(C)[O] ZOAMZFNAPHWBEN-UHFFFAOYSA-N 0.000 claims description 6
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 239000000543 intermediate Substances 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
- 125000005336 allyloxy group Chemical group 0.000 claims description 4
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 4
- WQJONRMBVKFKOB-UHFFFAOYSA-N cyanatosulfanyl cyanate Chemical class N#COSOC#N WQJONRMBVKFKOB-UHFFFAOYSA-N 0.000 claims description 4
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 230000001717 pathogenic Effects 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
- 150000003456 sulfonamides Chemical class 0.000 claims description 3
- 150000003461 sulfonyl halides Chemical class 0.000 claims description 3
- CPPKAGUPTKIMNP-UHFFFAOYSA-N Cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000004606 Fillers/Extenders Substances 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000005108 alkenylthio group Chemical group 0.000 claims description 2
- 125000000033 alkoxyamino group Chemical group 0.000 claims description 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 2
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 2
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000005109 alkynylthio group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 230000001276 controlling effect Effects 0.000 claims description 2
- 150000001913 cyanates Chemical class 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 2
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 2
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- MERLDXJKKQQWLA-UHFFFAOYSA-N prop-1-en-2-yloxymethylidyneoxidanium Chemical group [CH2-]C(=C)OC#[O+] MERLDXJKKQQWLA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 241000233866 Fungi Species 0.000 claims 3
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 2
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims 1
- 229940093912 Gynecological Sulfonamides Drugs 0.000 claims 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 1
- 125000005131 dialkylammonium group Chemical group 0.000 claims 1
- 229940079867 intestinal antiinfectives Sulfonamides Drugs 0.000 claims 1
- 229940005938 ophthalmologic antiinfectives Sulfonamides Drugs 0.000 claims 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 229940026752 topical Sulfonamides Drugs 0.000 claims 1
- 125000004367 cycloalkylaryl group Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 description 58
- 150000003254 radicals Chemical group 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 241000209094 Oryza Species 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 235000007164 Oryza sativa Nutrition 0.000 description 17
- 235000009566 rice Nutrition 0.000 description 17
- 239000007858 starting material Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 241000219146 Gossypium Species 0.000 description 15
- 241000209140 Triticum Species 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 235000021307 wheat Nutrition 0.000 description 15
- 229920000742 Cotton Polymers 0.000 description 14
- 241000231139 Pyricularia Species 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 239000003995 emulsifying agent Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- 241001049165 Caria Species 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000001939 inductive effect Effects 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 241000209048 Poa Species 0.000 description 7
- 241000896242 Podosphaera Species 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 241001310793 Podium Species 0.000 description 6
- 239000000370 acceptor Substances 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 125000002877 alkyl aryl group Chemical group 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 229920000151 polyglycol Polymers 0.000 description 6
- 239000010695 polyglycol Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 235000002639 sodium chloride Nutrition 0.000 description 6
- 235000011430 Malus pumila Nutrition 0.000 description 5
- 235000015103 Malus silvestris Nutrition 0.000 description 5
- 241000207763 Solanum Species 0.000 description 5
- 235000002634 Solanum Nutrition 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 230000001012 protector Effects 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 241000209136 Agropyron Species 0.000 description 4
- 241001330975 Magnaporthe oryzae Species 0.000 description 4
- 240000001047 Malus domestica Species 0.000 description 4
- 241000209149 Zea Species 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N benzohydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000003389 potentiating Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 241000219144 Abutilon Species 0.000 description 3
- 244000075850 Avena orientalis Species 0.000 description 3
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- 241000208296 Datura Species 0.000 description 3
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- 241001303487 Digitaria <clam> Species 0.000 description 3
- YQVMVCCFZCMYQB-UHFFFAOYSA-N Flamprop Chemical compound C=1C=C(F)C(Cl)=CC=1N(C(C)C(O)=O)C(=O)C1=CC=CC=C1 YQVMVCCFZCMYQB-UHFFFAOYSA-N 0.000 description 3
- 240000006669 Helianthus annuus Species 0.000 description 3
- 235000003222 Helianthus annuus Nutrition 0.000 description 3
- 235000017945 Matricaria Nutrition 0.000 description 3
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 3
- 101700003439 SOGA1 Proteins 0.000 description 3
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- 235000011684 Sorghum saccharatum Nutrition 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N Sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- 241000405217 Viola <butterfly> Species 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- 238000011081 inoculation Methods 0.000 description 3
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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- 238000005507 spraying Methods 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- GOCUAJYOYBLQRH-UHFFFAOYSA-N 2-[4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxyphenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl GOCUAJYOYBLQRH-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- 241000219318 Amaranthus Species 0.000 description 2
- 235000005781 Avena Nutrition 0.000 description 2
- 235000016068 Berberis vulgaris Nutrition 0.000 description 2
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- 240000002791 Brassica napus Species 0.000 description 2
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- 241000209200 Bromus Species 0.000 description 2
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 241001535157 Cynodon <characin> Species 0.000 description 2
- 241000234653 Cyperus Species 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N DABCO Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 241001465183 Drechslera Species 0.000 description 2
- RXCPQSJAVKGONC-UHFFFAOYSA-N Flumetsulam Chemical compound N1=C2N=C(C)C=CN2N=C1S(=O)(=O)NC1=C(F)C=CC=C1F RXCPQSJAVKGONC-UHFFFAOYSA-N 0.000 description 2
- 241001101998 Galium Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 240000007842 Glycine max Species 0.000 description 2
- 239000005562 Glyphosate Substances 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 241000207783 Ipomoea Species 0.000 description 2
- 241000209082 Lolium Species 0.000 description 2
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- IOXAXYHXMLCCJJ-UHFFFAOYSA-N oxetan-3-yl 2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC2COC2)=N1 IOXAXYHXMLCCJJ-UHFFFAOYSA-N 0.000 description 1
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- OYJMHAFVOZPIOY-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1 OYJMHAFVOZPIOY-UHFFFAOYSA-N 0.000 description 1
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- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention relates to novel sulfonyl amino (thio)carbonyl triazoline (thi)ons having alkenyl substituents of formula (I) in which Q1 represents oxygen or sulfur;Q2 represents oxygen or sulfur;R1 represents hydrogen, amino, alkylidene amino or a respective optionally substituted radical from the series of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkyl amino, dialkyl amino, alkanoyl amino, cycloalkyl, cycloalkyl alkyl, cycloalkyl amino, aryl and aryl alkyl;R2 optionally represents substituted alkenyl;R3 represents a respective optionally substituted radical from the series of alkyl, aryl alkyl, aryl and heteroaryl. The invention also relates to salts of the compounds of formula (I), to methods, to novel intermediate products for producing compounds of formula (I), and to the use thereof as herbicides and/or fungicides.
Description
SUFONILAMINO (IO) CARBORBONILTRIAZOLI (UNCLE) ONAS WHO HAVE ALQUENILOS SUBSTIENTS.
Field of the invention.
The invention relates to novel sulfonylamino (thio) carbonyltriazolin (thi) -ones' with alkenyl substituents, to various processes and to new intermediates for their preparation as well as to their use as agents for the treatment of plants, especially as herbicides and as fungicides.
Description of the prior art,
It is already known that certain sulfonylamino (thio) carbonyltriazolin (ti) onas exhibit herbicidal properties (cf. EP 341 489, EP 422469, EP 425948, EP 431291, EP 507171, WO 96/22982). However, the effect of these previously known compounds is not always satisfactory from all points of view.
REF. : 125156 Detailed description of the invention.
New sulfonylamino (thio) carbonyltriazoli (ti) onas with alkenyl substituents of the general formula (I) have now been found,
wherein Q1 represents oxygen or sulfur, represents oxygen or sulfur, R1 represents hydrogen, amino, alkylidenamino or represents a radical, optionally substituted respectively, of the series consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylamino, dialkylamino , alkanoylamino, cycloalkyl, cycloalkylalkyl, cycloalkylamino, aryl and arylalkyl, R 'represents alkenyl substituted if appropriate- and
R- represents a radical, respectively substituted, if appropriate, of the series consisting of alkyl, aralkyl, aryl and heteroaryl, as well as salts of the compounds of the formula (I). The novel sulfonylamino (thio) carbonyltriazolin (ti) onas are obtained with alkenyl substituents of the general formula (I), if (a) triazolin (ti) onas of the general formula (II) are reacted
wherein Q1, R1 and R2 have the meaning indicated above, with sulfonyliso (thio) cyanates of the general formula (III)
R3-S02-N = C = Q¿ (III)
wherein Q2 and R3 have the meaning indicated above, optionally in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent, or SI b) triazole (ti) ona derivatives are reacted of the general formula (IV)
wherein Q1 Q2, R1 and R2 have the meaning indicated above and Z represents halogen, alkoxy, aralkoxy or aryloxy, with sulfonic acid amides of the general formula
(V)
R -SO2-NH2 (V)
wherein R "has the meaning indicated above, if appropriate in the presence of an acid acceptor and, if appropriate, in the presence of a diluent, or if (c) triazolin (ti) ones of the formula are reacted general (II)
wherein Q1, R1 and R2 have the meaning indicated above, with sulfonamide derivatives of the general formula (VI)
RJ-S02-NH-CQ -Z (VI)
wherein Q2 and R3 have the meaning indicated above and Z represents halogen, alkoxy, aralkoxy or aryloxy, if appropriate in the presence of an acid acceptor and, if appropriate, in the presence of a diluent, or if (d) is they react triazolin (ti) onas of the general formula (II)
wherein Q1, R1 and R2 have the meaning indicated above, with sulfonyl halides of the general formula (VII)
R -S02-X (VII)
wherein R3 has the meaning indicated above, and
X represents halogen, and (thio) metal cyanates of the general formula
(VIII)
MQ -CN (VIII)
wherein Q2 has the above-mentioned meaning and M represents an alkali metal or alkaline earth metal equivalent, in the case in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent, and, if appropriate , the compounds obtained according to processes (a), (b), (c) or (d) of the formula (1), are converted into salts according to customary methods. The novel sulfonylamino (thio) carbonyl-triazolin (ti) onas with alkenyl substituents of the general formula (I) have interesting biological effects; they are characterized especially by a potent herbicidal and / or fungicidal activity. For the definitions in formula (I), it is fulfilled that: Preferably, R1 represents hydrogen, amino, alkylidenami, not with
1 to 6 carbon atoms, represents alkyl having 1 to 6 carbon atoms, optionally substituted by fluorine, chlorine, bromine, cyano, alkoxy with 1 to 4 carbon atoms, alkyl-carbonyl with 1 to 4 carbon atoms carbon atoms or by alkoxycarbonyl having 1 to 4 carbon atoms, represents alkenyl having 2 to 6 carbon atoms or alkynyl with 2 to 6 carbon atoms substituted, where appropriate, by fluorine, chlorine and / or bromine, represents alkyloxy with 1 to 6 carbon atoms or alkenyloxy with 2 to 6 carbon atoms, represents alkylamino with 1 a. 6 carbon atoms, di- (C 1 -C 4 -alkyl) -amino or alkyl-carbonylamino with 1- to 4-carbon atoms, optionally substituted respectively by fluorine and / or by chlorine, represents cycloalkyl with 3 to 6 carbon atoms carbon atoms or cycloalkylalkyl with 3 to 6 carbon atoms-alkyl having 1 to 4 carbon atoms substituted, where appropriate, by fluorine, chlorine, bromine and / or alkyl with 1 to 4 carbon atoms, or represents phenyl or phenyl-C 1 -C 4 -alkyl optionally substituted by fluorine, by chlorine, by bromine, by cyano, by nitro, by alkyl with 1 to 4 carbon atoms, by trifluoromethyl, by alkoxy with 1 to 4 carbon atoms and / or by alkoxycarbonyl having 1 to 4 carbon atoms. Preferably, it represents alkenyl having 2 to 6 carbon atoms, optionally substituted by cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, alkoxy with 1 to 4 carbon atoms or by alkoxycarbonyl with 1 to 4 carbon atoms. carbon. Preferably, R "represents the grouping
where R 4 and R 5 are the same or different and represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, alkyl having 1 to 6 carbon atoms, which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxy, by alkoxycarbonyl with 1 to 4 carbon atoms, by alkylaminocarbonyl with 1 to 4 carbon atoms, by di- (alkyl with 1 to 4 carbon atoms>) -aminocarbonyl, by alkoxy with 1 to 4 carbon atoms, by alkylcarbonyloxy with 1 to 4 carbon atoms, by alkoxycarbonyloxy with 1 to 4 carbon atoms, by alkylaminocarbonyloxy with 1 to 4 carbon atoms, by alkylthio with 1 to 4 carbon atoms, by alkylsulfinyl having 1 to 4 carbon atoms, by alkylsulfonyl with 1 to 4 carbon atoms, by di- (C1-C4alkyl> -aminosulfonyl, by cycloalkyl with 3 to 6 carbon atoms or by phenyl) , represents alkenyl with 2 to 6 carbon atoms (which is optionally substituted by fluorine, by chlorine, p or bromine, by cyano, by alkoxy-carbonyl with 1 to 4 carbon atoms or by phenyl), represents alkynyl with 2 to 6 carbon atoms (which is optionally substituted by fluorine, by chlorine, by bromine, by cyano, by alkoxycarbonyl having 1 to 4 carbon atoms or by phenyl), represents alkoxy with 1 to 4 carbon atoms (which is optionally substituted by fluorine, by chlorine, by bromine, by cyano, by alkoxycarbonyl with 1 to 4 carbon atoms; at 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by alkylthio with 1 to 4 carbon atoms, by alkylsulfinyl with 1 to 4 carbon atoms, by alkylsulfonyl with 1 to 4 carbon atoms or by cycloalkyl with 3 carbon atoms; at 6 carbon atoms), represents alkylthio having 1 to 4 carbon atoms (which is optionally substituted by fluorine, chlorine, bromine, cyano, carbon-carbon alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, for alkylsulfinyl with 1 to 4 carbon atoms or for alkylsulfonyl with 1 to 4 carbon atoms), represents alkenyloxy having 2 to 6 carbon atoms (which is optionally substituted by fluorine, chlorine, bromine, cyano or alkoxycarbonyl having 1 to 4 carbon atoms), represents alkenylthio with 2 to 6 carbon atoms (which is optionally substituted by fluorine, by chlorine, by bromine, by cyano, by nitro, by alkylthio with 1 to 3 carbon atoms
0 for alkoxy-carbonyl with 1 to 4 carbon atoms), represents alkynyloxy with 3 to 6 carbon atoms, alkynylthio with 3 to 6 carbon atoms or represents the radical -S (0) p-R6, where represents the numbers 1 or 2, and represents alkyl with 1 to 4 carbon atoms (which is optionally substituted by fluorine, chlorine, bromine, cyano or alkoxycarbonyl having 1 to 4 carbon atoms), represents alkenyl with 3 to 6 atoms of carbon, alkynyl with 3 to 6 carbon atoms, alkoxy with
1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkylamino with 1 to 4 carbon atoms, alkylamino with 1 to 4 carbon atoms, di- (alkyl with 1 to 4 carbon atoms) -amino, phenyl or represents the radical -NHOR7, where represents alkyl with 1 to 12 carbon atoms
(Which is optionally substituted by fluorine, by chlorine by cyano, by alkoxy with 1 to 4 carbon atoms, by alkylthio with 1 to 4 carbon atoms, by alkylsulfinyl with 1 to 4 carbon atoms, by alkylsulfonyl with 1 to 4 carbon atoms, by alkylcarbonyl with 1 to 4 carbon atoms, by alkoxycarbonyl with 1 to 4 carbon atoms, by alkylaminocarbonyl with 1 to 4 carbon atoms or by di- (alkyl with 1 to 4 carbon atoms) carbon atoms) -aminocarbonyl represents alkenyl with 3 to 6 carbon atoms (which is optionally substituted by fluorine, chlorine or bromine), represents alkynyl with 3 to 6 carbon atoms, cycloalkyl with 3 to 6 atoms of carbon, cycloalkyl with 3 to 6 carbon atoms-alkyl having 1 to 2 carbon atoms, phenylalkyl with 1 to 2 carbon atoms (which is optionally substituted by fluorine, chlorine, nitro, cyano, alkyl) with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms or by alkoxy-carbonyl or with 1 to 4 carbon atoms), represents diphenylmethyl or represents phenyl (which is optionally substituted by fluorine, by chlorine, by nitro, by cyano, by alkyl with 1 to 4 carbon atoms, by trifluoromethyl, by alkoxy with 1 to 4 carbon atoms, for fluoroalkoxy with 1 to 2 carbon atoms, for alkylthio with 1 to 4 carbon atoms, for trifluoromethyl or for alkoxycarbonyl with 1 to 4 carbon atoms), in addition R4 and / or R5 represent phenyl or phenoxy, represent alkyl-carbonylamino with 1 to 4 carbon atoms, alkoxy-carbonylamino with 1 to 4 carbon atoms, alkylaminocarbonyl-amino with 1 to 4 carbon atoms, di- (alkyl with 1 to 4 carbon atoms) -amino -carbonylamino, or represent the radical -CO-R8, where R8 represents hydrogen, alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, cycloalkoxy with 3 to 6 atoms of carbon, alkenyloxy with 3 to 6 carbon atoms, alkylthio with 1 to 4 carbon atoms, alkylamino with 1 to 4 carbon atoms, alkoxyamino with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkylamino with 1 to 4 carbon atoms or di- (alkyl with 1 to 4 carbon atoms) -amino (which are optionally substituted by fluorine and / or by chlorine), furthermore R 4 and / or R 5 represent trimethylsilyl, diazolinyl, 1,2-oxadiazol-5-yl, 3-methyl-1, 2,4-oxadiazol-5-yl, 1,3-dioxolan-2-yl, alkylsulfonyloxy with 1 to 4 carbon atoms, di- (alkyl with 1 to 4 carbon atoms) - aminosulfonylamino or represent the radical
-CH = N-R9, where R9 represents alkyl with 1 to 6 carbon atoms optionally substituted by fluorine, by chlorine, by cyano, by carboxy, by alkoxy with 1 to 4 carbon atoms, by alkylthio with 1 to 4 carbon atoms, by alkylsulfinyl with 1 to 4 carbon atoms or by alkylsulfonyl with 1 to 4 carbon atoms, represents benzyl optionally substituted by fluorine or by chlorine, represents alkenyl with 3 to 6 carbon atoms or alkynyl with 3 a 6 carbon atoms optionally substituted by fluorine or chlorine, represents phenyl optionally substituted by fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, trifluoromethyl, trifluoromethoxy or trifluoromethylthio, represents alkoxy with 1 to 6 carbon atoms, alkenyloxy with 3 to 6 carbon atoms, alkynyloxy with 3 to 6 carbon atoms or benzyloxy, optionally substituted by fluorine and / or chlorine, represents amino, alkylamino with 1 to 4 carbon atoms, di- (C 1 -C 4 -alkyl) -amino, phenylamino, alkyl-carbonylamino with 4 carbon atoms, alkoxycarbonylamino with 1 to 4 carbon atoms, alkyl-sulfonitamino with 1 to 4 carbon atoms or represents phenylsulfonylamino, optionally substituted by fluorine, chlorine, bromine or methyl. Preferably, in addition R3 represents the radical
where R 10 represents hydrogen or alkyl having 1 to 4 carbon atoms, R 11 and R 12 are the same or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, alkyl having 1 to 4 carbon atoms (which is optionally substituted by fluorine and / or by chlorine), alkoxy with 1 to 4 carbon atoms (which is optionally substituted by fluorine and / or by chlorine), carboxy, alkoxy-carbonyl with 1 to 4 carbon atoms, dimethylaminocarbonyl, alkylsulfonyl with 1 to 4 carbon atoms or di- (C 1 -C 4) alkyl - aminosulfonyl. Preferably, Rz also represents the radical
where R 13 and R, 1X 4 H are the same or different and denote hydrogen, fluorine, chlorine, bromine, nitro, cyano, alkyl having 1 to 4 carbon atoms (which is optionally substituted by fluorine and / or chlorine) or alkoxy with 1 to 4 carbon atoms (which is optionally substituted by fluorine and / or by chlorine). Preferably, R3 also represents the radical
where R 15 and R 16 are the same or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, alkyl having 1 to 4 carbon atoms, (which is optionally substituted by fluorine and / or chlorine), alkoxy with 1 at 4 carbon atoms (which is optionally substituted by fluorine and / or by chlorine), represents alkylthio having 1 to 4 carbon atoms, alkylsulfinyl having 1 to 4 carbon atoms or alkylsulfonyl having 1 to 4 carbon atoms (which are optionally substituted by fluorine and / or chlorine), represents aminosulfonyl, mono- (C 1 -C 4 -alkyl) -aminosulfonyl, represents di- (C 1 -C 4 -alkyl) - aminosulfonyl or alkoxy- carbonyl with 1 to 4 carbon atoms or dimethylaminocarbonyl). Preferably, R3 also represents the radical
where R 17 R 18 are the same or different and represent hydrogen, fluorine, chlorine, bromine, alkyl having 1 to 4 carbon atoms (which is optionally substituted by fluorine and / or bromine), alkoxy with 1 to 4 carbon atoms, carbon (which is optionally substituted by fluorine and / or by chlorine), represents alkylthio having 1 to 4 carbon atoms, alkylsulfinyl having 1 to 4 carbon atoms or alkylsulfonyl having 1 to 4 carbon atoms (which are substituted if necessary) given by fluorine and / or by chlorine), or represents di- (alkyl with 1 to 4, carbon atoms) -aminosulfonyl. Preferably, R3 also represents the radical
R 20 where R 19 and R, 20 are the same or different and represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, alkyl having 1 to 4 carbon atoms (which is optionally substituted by fluorine and / or chlorine) alkoxy with 1 to 4 carbon atoms (which is optionally substituted by fluorine and / or chlorine), alkylthio having 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms or alkylsulfonyl with 1 to 4 carbon atoms carbon (which are optionally substituted by fluorine and / or by chlorine), di- (C 1 -C 4 -alkyl) - aminosulfonyl, alkoxycarbonyl with 1 to 4 carbon atoms or dimethylaminocarbonyl, and A represents oxygen, sulfur or the group NT, where T represents hydrogen, alkyl having 1 to 4 carbon atoms (which is optionally substituted by fluorine, chlorine, bromine or cyano), cycloalkyl with 3 to 6 carbon atoms, benzyl, phenyl (which is optionally substituted by fluorine, chlorine, bromine or nitro), alkyl carbonyl with 1 to 4 carbon atoms, alkoxycarbonyl with 1 to 4 carbon atoms or di- (alkyl with 1 to 4 carbon atoms) -aminocarbonyl. Preferably, RJ also represents the radical
where R21 and R22 are the same or different and represent hydrogen, alkyl having 1 to 4 carbon atoms, halogen, alkoxy-carbonyl with 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms . Y1 represents sulfur or the grouping N-R23, where
R23 represents hydrogen or alkyl having 1 to 4 carbon atoms. Preferably, R3 also represents the radical
where R 24 represents hydrogen, alkyl having 1 to 4 carbon atoms, benzyl, pyridyl, quinolinyl or phenyl, R 25 represents hydrogen, halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms (which is optionally substituted by fluorine and / or - by chlorine), alkoxy with 1 to 4 carbon atoms - (which is optionally substituted by fluorine and / or by chlorine), dioxolanyl or alkoxycarbonyl with 1 to 4 carbon atoms and R represents hydrogen, halogen or alkyl with 1 to 4 carbon atoms.
The objects of the invention are preferably also the sodium, potassium, magnesium, calcium, ammonium, alkyl ammonium salts with
1 to 4 carbon atoms, di- (C 1 -C 4) alkyl-ammonium, tri- (C 1 -C 4) alkyl- ammonium, tetra- (C 1 -C 4) alkyl carbon) -ammonium, tri- (C 1 -C 4 -alkyl) -sulfonium, cycloalkylammonium with 5 or 6 carbon atoms and di- (alkyl with 1 a)
2 carbon atoms) -benzyl ammonium of the compounds of the formula (I), in which Q1, Q2, R1, R2 and R3 have the meanings indicated above in a preferred manner. In particular, R 1 represents methyl, ethyl, n- or i-propyl, which may be substituted, if appropriate, by fluorine, chlorine, cyano, methoxy or ethoxy, represents propenyl, butenyl, propinyl or butynyl, respectively substituted by fluorine. , by chlorine or by bromine, represents methoxy, ethoxy, n- or i-propoxy or represents allyloxy, represents methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino, or represents cyclopropyl optionally substituted by fluorine, by chlorine , by bromine, by methyl or by ethyl. In particular, R 2 represents ethenyl, propenyl or butenyl substituted, where appropriate, by cyano, fluorine, chlorine and / or bromine. Especially, R3 represents the radical
where R 4 represents fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, 2-chloro-ethoxy, 2-fluoro-ethoxy, , 2-di-fluoro-ethoxy, 2,2,2-trifluoro-ethoxy, 1,1,2,2-tetrafluoro-ethoxy, 1, 1, 2, 2, 2-pentafluoroethoxy, '2-methoxy-ethoxy, cyclopropylmethoxy , methylthio, ethylthio, n- or i- propylthio, 2-fluoro-ethylthio, allyloxy, propargyloxy, methylsulfinyl, ethylsulfoyl, methylsulfonyl, ethylsulphonyl, dimethylaminosulfonyl, diethylaminosulfonyl, N-methoxy-N-methylaminosulfonyl, phenyl, phenoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl and R5 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-o-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio or ethylthio . Especially, R3 also represents the radical
where R 10 represents hydrogen, R represents fluorine, chlorine, bromine, methyl, methoxy,
? difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyl or dimethylaminosulfonyl, R 12 represents hydrogen. Especially, R3 also represents the radical
where R represents methyl, ethyl, n- or i-propyl Especially, R3 further represents the radical
where R < represents methyl, ethyl, n-i-propyl, phenyl or pyridyl, R represents hydrogen, fluorine, chlorine or bromine and R26 represents fluorine, chlorine, bromine, methoxycarbonyl or ethoxycarbonyl.
The definitions of the radicals - previously given in a general manner or indicated in the preferred ranges - are valid both for the final products of the formula (I) as well as, correspondingly, for the starting materials or the intermediate products required respectively for obtaining. These definitions of the radicals can be combined arbitrarily with each other, that is to say even between the indicated ranges of the preferred compounds. According to the invention, those compounds of the formula (I) are preferred, in which a combination of the meanings indicated above is preferably present. According to the invention, those compounds of the formula (I) are particularly preferred, in which a combination of the meanings given above is particularly preferred.
The hydrocarbon radicals, cited in the definitions of the radicals, such as alkyl, alkenyl or alkynyl, even in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino, can be straight chain or branched chain, even when this is not Indicate expressly. In general halogen represents fluorine, chlorine, bromine or iodine, preferably represents fluorine, chlorine or bromine, especially represents fluorine or chlorine. In certain compounds according to the invention of the formula (I), cis / trans isomers may be present. The invention covers in these cases respectively both geometric isomers as well as their mixtures (in any quantitative proportion). If they are used, for example 2-trifluoromethoxy-phenylsulfonyl-isocyanate and 4-ethyl-5- (2-fluoro-propen-1-yl) -2,4-dihydro-3H-1,2,4-triazole- 3-one (trans isomers) as starting materials, the development of the reaction in the case of process (a) according to the invention can be schematized by means of the following formula scheme:
If, for example, 2-ethylthio-benzenesulfonamide and 2-chlorocarbonyl-4-cyclopropyl-5- (1,2-dichloro-propen-1-yl) -2,4-dihydro-3H-1, 2 are used , 4-triazol-3-one (trans isomer) as starting materials, the development of the reaction in the case of process (b) according to the invention can be schematized by means of the following formula scheme:
If, for example, N-methoxycarbonyl-2-methoxy-benzenesulfonamide and the 5- (1-brorno-propen-2-yl) - methy1-2, 4-dihydro-3H-1, 2, 4 are used triazol-3-one (trans isomer) as starting materials, the development of the reaction in the case of process (c) according to the invention can be schematized by means of the following formula scheme:
If, for example, 2-chloro-6-methyl-benzenesulfonyl chloride, 4-allyl-5- (propen-1-yl) -2,4-dihydro-3H-1,2,4-triazole are used -3-one (trans isomer) and potassium cyanide as starting materials, the development of the reaction in the case of process (d) according to the invention can be schematized by means of the following formula scheme:
The triazolin (ti) onas to be used as starting materials in the processes according to the invention (a) (C) and (d) for the preparation of the compounds of the formula (I), are generally defined by means of the formula (II). In the formula (II), Q1, R1 and R2 preferably have or especially those meanings which have already been mentioned above, preferably or very particularly preferably for Q1, R1 and R2 in connection with the description of the compounds of the invention. Formula (I) according to the invention.
The triazoles (ti) onas of the general formula (II) are not yet known from the literature: they constitute, as new products, also an object of the present application. The new triazolin (ti) onas of the general formula (II) are obtained, if (a) iso (thio) cyanates of the general formula (IX) are reacted
Q1 = C = N-R1 (IX)
wherein Q1 and R1 have the meaning indicated above, with hydrazides of the general formula (X)
H? N-NH-CO-R "(X)
wherein R2 has the meaning indicated above, if appropriate in the presence of diluents, such as, for example, isopropanol or water, if appropriate in the presence of a reaction auxiliary agent / such as, for example, sodium hydroxide, at temperatures comprised between 0 ° C and 100 ° C [it is possible to present an isomerized as a consequence of the displacement of the double bond] and it is elaborated in the usual way (see the preparation examples), or if (ß) are reacted (thio) semicarbazides of the formula general (XI)
wherein R1 and Q1 have the meaning indicated above, with carboxylic acids or with their derivatives of the general formula (XII)
R -CO-Y (XII)
wherein R 'has the meaning indicated above, and
Y represents hydroxy, halogen or the grouping -O-CO-R2, optionally in the presence of a diluent, such as for example sulfolane, optionally in the presence of a reaction auxiliary agent such as, for example, sodium hydroxide. and, if appropriate, in the presence of a stabilizer, such as, for example, hydroquinone, at temperatures between 0 ° C and 100 ° C and processed in the usual manner (see the preparation examples). The sulfonyliso (thio) cyanates to be further used as starting materials in the case of the process (a) according to the invention for the preparation of the compounds of the formula (I), are generally defined by means of the formula (III) . In the formula (III), Q2 and R3 preferably have or especially those meanings which have already been mentioned above in a preferred manner or, more preferably, for Q2 and R3 in relation to the description of the compounds of the formula (I) . The starting materials of the formula (III) are known and / or can be prepared according to processes known per se (see US Pat. No. 4,127,405, US Pat. No. 4,197,919, US Pat. No. 43,713,991, EP-A 7,687. EP-A 13480, EP-A 21641, EP-A 23141, EP-A 23422, EP-A 30139, EP-A 35893, EP-A-44808, EP-A 44809, EP-A 48143, EP-A 51466, EP-A 64322, EP-A 70041, EP-A 173312). The triazolin (ti) -one derivatives, to be used as starting materials in the process (b) according to the invention for the preparation of the compounds of the general formula (I), are generally defined by the formula ( IV). In the formula (IV) Q1, Q2, R1 and R2 preferably have or especially those meanings which have already been mentioned above, preferably or particularly preferably for Q1, Q2, R1 and R2 in relation to the description of the compounds of the formula- (I); preferably Z represents fluorine, chlorine, bromine, methoxy, ethoxy, benzyloxy or phenoxy, especially represents methoxy or phenoxy. The starting materials of the formula (IV) are not yet known from the literature, - they constitute, as new products, also an object of the present application. The new compounds of the formula (IV) are obtained, if triazolin (ti) onas of the general formulas (II) are reacted
wherein Q1, R1 and R2 have the meaning indicated above, with carbonic acid derivatives of the general formula (XIII)
Z-CQ2-ZX (XIII)
wherein Q2 and Z have the meaning indicated above, and Z1 represents halogen (especially chloro), alkoxy
(especially methoxy), aralkoxy (especially benzyloxy) or aryloxy (especially phenoxy), if appropriate in the presence of an acid acceptor, such as, for example, sodium or potassium hydride, sodium or potassium hydroxide, t-butanolate sodium or potassium and, if appropriate, in the presence of a diluent, such as for example tetrahydrofuran or dimethoxyethane, or in a two-phase system consisting of water and an organic solvent, such as, for example, methylene chloride or chloroform, at temperatures between 0 ° C and 100 ° C. The sulphonic acid amides to be used further as starting materials in the process (b) according to the invention, for the preparation of the compounds of the general formula (I), are generally defined by the formula (V) . In the formula (V), R 3 preferably has or especially that meaning which has been previously indicated in a preferential manner or, more preferably, for R 3 in relation to the description of the compounds of the formula (I). The starting materials of the formula (V) are known and / or can be prepared according to processes known per se (see US-P 4127405, US-P 4169719, US-P 4371391, EP-A 7687, EP-A 13480, EP-A 21641, EP-A 23141, EPA 23422, EP-A-30139, EP-A 35893, EP-A 44808, EP-A 44809, EP-A 48143, EP-A 51466, EP-A 64322 , EP-A 70041, EP-A 173312). The sulphonic acid amide derivatives to be used as starting materials in the process according to the invention for the preparation of the compounds of the formula (I) are generally defined by the formula ( VI) In the formula (VI), Q2 and R3 preferably have or especially those meanings that have already been mentioned above, preferably or even more preferably for Q2 and R3 in relation to the description of the compounds of the formula (I), preferably Z represents fluorine, chlorine, bromine, methoxy, ethoxy, benzyloxy or phenoxy, especially represents methoxy or phenoxy The starting materials of the formula (VI) are known and / or can be prepared according to processes per se The sulfonyl halides, to be used as starting materials in the case of the process (d) according to the invention, for the preparation of the compounds of the formula "(I), are defined in g eneral by means of formula (VII). In the formula (VII), R 3 preferably has or especially that meaning which has already been mentioned above, preferably or even more preferably for R 3 in relation to the description of the compounds of the formula (I); Preferably, X represents fluorine, chlorine or bromine, especially chlorine. The starting materials of the formula (VII) are known and / or can be prepared according to methods known per se. The new intermediates of the above formulas (II) and (IV) differing only because the 2-position is unsubstituted or substituted by an acyl radical -CQ2-Z, can be described together by means of the formula (XIV) :
wherein R3, R2 and Q1 have the meanings previously in the formula (I), and A represents hydrogen or the group -CQ2-Z, where Q2 has the meaning previously indicated in the formula (I) and Z represents halogen, alkoxy , aralkoxy or aryloxy. With regard to the preferred and especially preferred meanings of all the variable radicals of the formula (XIV), the indications given above for the compounds of the formulas (II) or (IV) are valid. The processes (a), (b), (c) and (d) according to the invention, for obtaining the new compounds of the formula (I), they are preferably carried out using diluents. Suitable diluents in this case are practically all inert organic solvents. These preferably include aliphatic and aromatic hydrocarbons, if appropriate halogenated, such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, tetrachloromethane, chlorobenzene and o-dichlorobenzene; ethers such as diethyl and dibutyl ether, glycol dimethyl ether, and diglycoldimethyl ether, tetrahydrofuran and dioxane; ketones, such as acetone, methyl-ethyl-, methyl-isopropyl- and met-il-isobutyl-ketone; esters such as methyl acetate and ethyl acetate; nitriles such as, for example, acetonitrile and propionitrile; amides, such as for example dimethylformamide, dimethylacetamide and N-methylpyrrolidone, as well as dimethyl sulfoxide, tetramethylene sulfone and hexamethylphosphorotriamide. As reaction aids or as acid acceptors, they can be used. in the processes (a), (b), (c) and (d) according to the invention, all the acid acceptors usually usable for this type of reactions. Preference is given to alkali metal hydroxides, such as, for example, sodium and potassium hydroxide, alkaline earth metal hydroxides, such as, for example, calcium hydroxide, carbonates and alkali metal alcoholates, such as sodium and potassium carbonate, tere. sodium and potassium butylate, in addition basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, ethyldiisopropylamine, ethyldicylohexylamine, N, N-dimethylbenzylamine, N, N-dimethylaniline, pyridine, 2-methyl- , 3-methyl-, 4-methyl-, 2, -dimethyl-, 2,6-dimethyl-, 2-ethyl-, 4-ethyl- and 5-ethyl-2-methyl-pyridine, 1,5-diazabicic it [4, 3, 0] -non-5-ene (DBN), 1, 8-diazabicyclo [5, 4, 0] -undec-7-ene (DBU) and 1, -diazabicyclo [2.2, 2 ] -octane (DABCO). The reaction temperatures in processes (a), (b), (c) and (d) according to the invention can vary within wide limits. In general, work is carried out at temperatures between -20 ° C and + 100 ° C, preferably at temperatures between 0 ° C and + 80 ° C. The processes (a), (b), (c) and (d) according to the invention are generally carried out under normal pressure. However, it is also possible to work under higher pressure or at a lower pressure. To carry out the procedures
(a), (b), (c) and (d) according to the invention, the starting materials required in each case are used, in general, in approximately equimolar quantities.
However, it is also possible to use one of the components, used in each case, in a larger excess. The reactions are carried out, in general, in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the necessary temperature in each case. The processing is carried out in the case of processes (a), (b), (c) and (d) according to the invention respectively according to usual methods (see the preparation examples). Compounds can be prepared, if appropriate, from the compounds according to the invention of the general formula (I). Such salts are obtained in a simple manner according to usual methods of salt formation, for example by dissolving or dispersing a compound of the formula (I) in a suitable solvent, such as, for example, methylene, acetone, tere. -butylmethylether or toluene, and addition of a suitable base. The salts can then be isolated, if appropriate after prolonged stirring, by evaporation or by suction filtration. The active compounds according to the invention can be used as defoliants, desiccants, herbicidal agents and especially as weed killers. By weeds, in the broadest sense, we must understand the plants that grow in places where they are unwanted. The fact that the substances according to the invention act as total or selective herbicides depends essentially on the amount used. The active compounds according to the invention can be used, for example, in the following plants:
Bad dicotyledonous herbs of the following classes: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum , Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
Dicotyledonous crops of the classes: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopers-icon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.
Bad monocotyledonous herbs of the following kinds: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Oats, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Saginaria, Eleocharis, Scirpus, Paspalum , Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
Cultures of monocotyledonous classes: Oryza, Zea, Triticum, Hordeum, Avena, Sécale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.
The use of the active compounds according to the invention, however, is not limited in any way to these classes, but they also extend equally over other plants. The active compounds according to the invention are suitable, depending on the concentration, for totally combating weeds, for example, in industrial and road installations and on roads and squares, with and without tree growth. In the same way, the compounds can be used to control weeds in permanent crops, for example, in forest facilities, ornamental trees, fruit trees, vineyards, citrus trees, walnut trees, bananas, coffee, tea, rubber oil palms, cocoa, berries and hops, on ornamental and sports paths and on meadows and to selectively control weeds in mono-annual crops. The compounds according to the invention of the formula (I) are especially suitable for selectively controlling the bad "monocotyledonous and dicotyledonous herbs in monocotyledonous and dicotyledonous cultures, both in the pre-emergence procedure and in the post-emergence procedure. The products according to the invention have a potent microbicidal effect and can be used in practice to combat unwanted microorganisms, thus the active ingredients are suitable, in suitable concentrations, for use as fungicides and / or bactericides. Fungicidal agents are used in the protection of plants for the fight against plasmodioforomycetes, oomycetes, chytridiomycetes, zygomycetes, ascomycetes, basidiomycetes, deuteromycetes. Bactericidal agents are used in the protection of plants to combat pseudomanacea, rhizobiaceous, enterobacteriaceous, corynebacteriaceous and streptomycete. Some pathogens of fungal and bacterial diseases, which fall within the general definitions listed above, may be cited by way of example, but without any limiting character: type of Xanthomonas, such as, for example, Xanthomonas campestris pv. Oryzae; Pseudomonas types, such as, for example, Psendomonas syringae pv. lachrymans; Erwinia types, such as, for example, Erwinia amylovora; Pythium types, such as for example Pythium ultimun; Phytophthora types, such. such as Phytaphthora infestans; Pseudoperonospora types, such as, for example, Pseudoperonospora hu uli or Pseudoperonospora cubensis; types of Plasmapara, such as for example Plasmopara viticola; Bremia types, such as, for example, Bremia lactucae;
Peronospora types, such as, for example, Peronospora pisi or P. brassicae; Erysiphe types, such as for example Erysiphe graminis; Sphaerotheca types, such as for example Sphaerotheca fuliginea; Podosphaera types, such as, for example, Podosphaera leucotricha; Venturia types, such as, for example, Venturia inaequalis; types of Pyrenophora, such as, for example, Pyrenophora teres or P. gramínea; (form of conidia, Drechslera, synonym: Helminthosporium); Cochliobolus types, such as, for example, Cochliobolus sativus (forms of conidia, Drechslera, synonym: Henminthosporium); Uromyces types, such as, for example, Uromyces appendiculatus; Puccinia types, such as Puccinia recondita; Sclerotinia types, such as, for example, Sclerotinia sclerotiorum; types of Tilletia, such as for example Tilletia caries; types of Ustilago, such as, for example, Ustilago nuda or Ustilago avenae; Pellicularia types, such as, for example, Pellicularia sasakii; types . of Pyricularia, such as for example Pyricularia oryzae; Fusarium types, such as for example Fusarium culmorum; Botrytis types, such as for example Botrytis cinerea; Septoria types, such as, for example, Septoria nodorum; types of Leptosphaeria, such as for example Leptosphaeria nodorum; Cercospora types, such as, for example, Cercospora canescens; Alternaria types, such as for example Alternaria brassicae; types of Pseudocercosporella, such as for example Pseudocercosporella herpotrichoides
The good compatibility with the plants and the active products at the concentrations necessary for the fight against plant diseases allows a treatment of the aerial parts of the plants, of seedlings and seeds and of the soil. In this case, the active compounds according to the invention can be used, with particularly good success, for the control of diseases in fruit and vegetable plantations, such as, for example, against Podosphaera types, as well as for combating rice diseases, such as, for example, Pyricularia oryzae (protector and systemic). The active ingredients can be converted into customary formulations, such as solutions, emulsions, sprayable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with the active compound , as well as micro-encapsulations in polymer materials. These formulations are prepared in known manner, for example, by mixing the active ingredients with extender materials, that is, with liquid solvents and / or solid excipients, if appropriate, using surfactants, - that is, emulsifiers and / or dispersants and / or foam generating means. When using water as a filler, it is also possible, for example, to use organic solvents as auxiliary solvents. Suitable liquid solvents are, in particular, aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane, or paraffins, for example, fractions of crude oil, mineral and vegetable oils, alcohols such as butanol, or glycol, as well as their esters and ethers, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone, solvents strongly polar such as dimethylformamide and dimethyl sulfoxide, as well as water. Suitable solid excipients are, for example, ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earths and molten synthetic minerals, such as silicic acid, highly dispersed , aluminum oxide and silicates, as solid excipients for granulates come into consideration: for example, broken and fractionated natural minerals such as calcite, marble, pumice, sepiolite, dolomite, as well as synthetic granules of inorganic and organic flours, as well as granulates of organic materials, such as sawdust, coconut husks, corn ears and tobacco stems; - as emulsifiers and / or foam generators are suitable, for example, nonionic and anionic emulsifiers, such as polyoxyethylenated esters of fatty acids, polyoxyethylenated ethers of fatty alcohols, such as, for example, alkylaryl polyglycol ether, alkylsulfonates, alkyl sulfates, arylsulfonates, such as albumin hydrolysates; Dispersants are suitable as dispersants: for example, sulfitic leaching of lignin and methylcellulose. Adhesives such as carboxymethylcellulose, natural and synthetic polymers powdery, granulated or in the form of latex, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids, such as cephalin and lecithin, and phospholipids can be used in the formulations. synthetic Other additives can be mineral and vegetable oils.
Dyes, such as inorganic pigments, for example, iron oxide, titanium oxide, ferrocyanic blue and organic dyes, such as alizarin dyes, metallic azo and phthalocyanine dyes and trace nutrients, such as iron salts, can be employed. manganese, boron, copper, cobalt, molybdenum and zinc. The formulations generally contain between 0.1 to 95% by weight of active compound, preferably between 0.5 and 90%. The active compounds according to the invention can be used as such or in their formulations, even in admixture with known herbicides for the control of weeds, with possible finished formulations or tank mixtures. Suitable mixtures are known herbicides, for example:
Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amidochlor, aAraidosulfuron, Anilofos, Asulam, Atre, Azafenidin, sulfuron, Benazolin (-ethyl), Benfuresate, Bensulfuron (-methyl), Bentazon, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromophenoxy, Bromoxynil, Butachlor, Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyfen, Chloramben, Chloridazon, Chlorimuron ( -ethyl), Chlornitrofen, Chlorsulfuon, Chlortoluron, Cinmethylin, Cinosul furon, Clethodim, Clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Cloransulam (-methyl), Cumyluron, Cyane, Cycloate, Cyclosulfamuron, Cycloxydim , Cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Diclosulam, Diethatyl (-ethyl), Difenzoquat, Diflufenican, Diflufenzopyr , Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Di Methenamid, Dimexyflam, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epoprodan,
EPTC, Esprocarb, Ethalfluralin, Ethametsulfúron
(-methyl), Ethofumesate, Ehoxyfen, Ethoxysulfuron,
Etobenzanid, Fenoxaprop (-P-ethyl), Flamprop
(-isopropyl), Flamprop (-isopropyl-L), Flamprop (-methyl), Flazasulfuron, Fluop (-P-butyl), Flumetsulam, Flumiclorac (-pentyl), Flumiox, Flumipropyn, Flumetsulam, Fluometuron,
Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Flupropacil, Flupyrsul furon (-methyl, -sodium), Flurenol (-butyl), Fluridone, Fluroxypyr (-meptyl), Flurpri idol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen , Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl), Haloxyfop (-P-metito), Hexone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Iodosulfuron , Ioxynil, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Meta itron, Metazachlor, Methabenzthiazuron,
Metobenzuron, Metobromuron, (alpha-) Metolachlor,
Metosulam, Metoxuron, Metribuzin, Metsulfuron
(-methyl), Molinate, Monolinuron, Naproanilide,
Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxlomefone, Oxyfluorfen, Paraquat, Pelargonic acid, Pendimethalin, Pentoxazone, Phenmedipham, Piperophos, Pretilachior, Primisulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaqui zafop, Propisochlor, Propyzamide, Prosulfocarb, Prosulfuron, Pyraflufen (-ethyl), Pyrazolate, Pyrazosulfuron (-ethyl), Pyrazoxyfen, Pyribenzoxim, Pyributicarb, Pyridate, Pyriminobac (-methyl), Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quinoclamine, Quizalofop (-P-ethyl), Quizalofop (-P-tefuril), Rimsulfuron, Sethoxydim, Sime, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebuthiuron, Terbuthyle, Terbutryn, Thenylchlor, Thiafluamide, Thiazopyr, Thidiin, Thifensulfuron (-methyl), Thiobencarb, Thiocarb, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-methyl), Triclopyr, Tridiphane, Trifluralin and Triflusulfuron. A mixture with other known active substances is also possible, such as fungicides, insecticides, acaricides, nematicides, protective substances against ingestion by birds, nutrient substances of the plants and means for improving the structure of the ground. The active compounds can be used as such, in the form of formulations or of the forms of application prepared therefrom by further dilutions, such as ready-to-use solutions. Suspensions, emulsions, powders, pastes and granules. The use is carried out in the usual way, for example, by watering, spraying, spraying, spreading. The active products according to the invention can be applied both before and after the outbreak of the plants. They can also be incorporated into the soil before sowing. The amount of active product used can vary within a wide range. This depends fundamentally on the type of the desired effect. In general, the amounts used are between 1 g and 10 kg of active product per hectare of land surface, preferably between 5 g and 5 kg per hectare. The preparation and use of the active substances according to the invention are deduced from the following examples:
Examples of obtaining
Example 1
Procedure (a))
A mixture consisting of 1.4 g (10 mmol) of 4-methyl-5- (propen-1-yl) -2, -dihydro-3H-1,2,4-triazol-3-one [trans isomer (11)) is stirred. -1)], 3.0 g (12 mmol) of 2-difluoromethoxy-phenylsulfonyl isocyanate and 40 ml of acetonitrile for 15 hours at room temperature (approximately 20 ° C) and then concentrated by vacuum evaporation of the pump. Water. The residue is stirred with isopropanol / petroleum ether and the crystalline product is isolated by suction filtration. 3.7 g (95% of theory) of 2- (2-difluoromethoxy-phenylsulfonylamino-carbonyl) 4-methyl-5- (propen-1-yl) -2,4-dihydro-3H-1, 2 are obtained, 4-triazol-3-one [trans form] with a melting point of 173 ° C.
Example 2
. { Procedure (b)). 2.64 g (10 mmol) of N, N-dimethyl-benzene-1, 2-4-disulfonamide in 30 ml of toluene are collected and combined at room temperature (about 20 ° C) with 1.52 g (10 g). mmoles) of 1,8-diazabicyclo- [5, 4, 0] -undec-7-ene (DBU). The mixture is stirred for 30 minutes at room temperature and then combined, dropwise, with a solution of 2.6 g (10 mmol) of 4-methyl-2-phenoxycarbonyl-5- (propen-1-yl) -2, 4-dihydro-3H-1,2,4-triazol-3-one [mixture of isomers: 70% trans / 30% cis) in 25 ml of acetonitrile. The reaction mixture is stirred for 4 hours at room temperature and then concentrated by evaporation under vacuum of the water pump. The residue is shaken with methylene chloride and with 2N hydrochloric acid, the organic phase is separated, dried with sodium sulfate and filtered. The filtrate is concentrated by evaporation under vacuum of the water pump, the residue is stirred with ethyl acetate / petroleum ether and the crystalline product is isolated by suction filtration. 2.5 g (58% of theory) of 2- (2-dimethylaminosulfonyl-phenylsulfonylamino-carbonyl) 4-methyl-5- (propen-1-yl) -2,4-dihydro-3H-1, 2 are obtained. 4-triazol-3-one with a melting point of 163 ° C [as a mixture of isomers: 72% trans / 28% cis]. In a manner analogous to that of the preparation examples 1 and 2, and also according to the general description of the preparation processes according to the invention, for example, the compounds of the formula (I) indicated in the following table 1 can also be prepared.
Table 1: Examples of compounds of the formula (I)
Table 1: (Continued)
Table 1: (Continued)
Table 1: (Continued)
Table 1: (Continued)
Table 1: (Continued)
Table 1: (Continued)
Observations concerning the stereochemical indications of R2.
1) The products of the formula (I) prepared from the trans isomer (II-l) described below, all have also - the trans configuration (designated "trans"). 2) The same is valid for all active products (I) prepared from the trans (II-4) isomer. The trans (II-4) isomer is formed by its synthesis already with a purity of > 95%; the cis isomer has not been isolated yet. 3) In some cases they were transformed, however, from the cis / trans (II) mixtures obtained from the mother liquors of the triazolinone (II), in the corresponding phenylurethanes (IV) (also a mixture of cis isomers) / trans) and then reacted (V) according to the obtaining process (b) to give the active products (I), which were then also mixtures of cis / trans isomers of variable composition, according to the solubility of the isomers. In these cases the composition of the isomers of the final product obtained (I) has been given as a percentage (%) (determined from the corresponding 1H-NMR spectrum). In this way, for example, the indication
Trans / cis 72:28 represents for the corresponding active product a composition of the isomers of 72% trans isomer and 28% cis isomer.
4) The two CH groups: - in the intermediate product (II-6) and also in the active products (I), prepared from them, according to examples 49-53 are found as indicated in the cis position of according to the 2D-NMR measurement.
Starting products of the formula (II):
Example (II-l)
283 g (4.97 moles) of methyl isocyanate are added over the course of 1 hour, dropwise, under stirring, to an ice-cooled solution of 526 g (4.97 moles) of vinylacetic acid hydrazide in 1 liter. of isopropanol. The reaction mixture is stirred for another 30 minutes at room temperature (about 20 ° C) and then combined, under ice-cooling, with 800 ml of water and 800 g of 50% sodium hydroxide solution. The mixture is then heated, in the course of about 30 minutes, to 80 ° C and heated to reflux for 2 hours. The mixture is then concentrated by evaporation under vacuum of the water pump, approximately up to half its volume and neutralized with 1 kg of concentrated hydrochloric acid. It is then concentrated by evaporation under reduced pressure, the residue is taken up in 1,500 ml of N, N-dimethylformamide, the undissolved common salt is separated by filtration and the filtrate is concentrated again by evaporation under reduced pressure. The residue is distilled at approximately 1 mbar. 422 g (55% of the theory) are obtained from 4-methy1-5- (propen-1-yl) -2,4-dihydro-3H-1, 2,4-triazol-3-one with a fusion of 140 ° C (at 1 mbar) as a mixture of cis / trans isomers [evidently formed as a consequence of isomerization of the double bond in the course of the reaction, the radical (propen-3-yl) isomerized of the hydrazide of vinylacetic acid, with the double bond isolated, located at the end of the chain, to give the radical (propene-1-yl) with the double bond conjugated (cis / trans)]. The product solidifies (melting point: 94 ° C); it is constituted by 81.5% by the trans isomer and by 18.5% by the cis isomer. The mixture of the isomers can be recrystallized from a two times greater amount of ethyl acetate and then provides about 130 g of the pure trans (II-1) isomer with a melting point of 112 ° C.
Example (II-2)
A mixture consisting of 178 g (2.0 mol) of 4-methyl-semicarbazide, 10 g of hydroquinone and 250 ml of sulfolane is combined, under ice-cooling, with 339 g (2.0 mol) of methacrylic anhydride; the reaction mixture is stirred for another 15 minutes at room temperature (about 20 ° C), then combined with 640 g of 25% sodium hydroxide solution and stirred for 2 hours at 80 ° C. After cooling to room temperature, it is neutralized with concentrated hydrochloric acid and concentrated by evaporation under reduced pressure. The residue is extracted hot with toluene. The product crystallizes by cooling the extraction solution; it is isolated by filtration by suction. 70 g (25% of theory) of 4-methyl-5- (propen-2-yl) -2,4-dihydro-3H-1, 2,4-triazol-3-one are obtained with a point of fusion of 85 ° C. Analogously to the preparation examples (II-1) and (II-2), it is also possible, for example, to prepare the compounds of the formula (II) indicated in Table 2 below (in relation to the stereochemical data relating to R 2). see the observations given above in Table 1).
(II) Table 2: Examples of compounds of the formula (II)
Table 2: (Continued)
Application examples: With regard to the stereochemistry of the test compounds, the indications belonging to Table 1 above are valid.
Example A.
Pre-emergence trial
Solvent: 5 parts by weight of acetone. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether.
To obtain a convenient preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent, the amount is added. of indicated emulsifier and the concentrate is diluted with water to the desired concentration. Seeds are sown from the test plants in normal soil. After about 24 hours, the soil is sprayed with the preparation of the active product in such a way that the desired amount of active compound per unit area is applied respectively. The concentration of the spray mixture will be chosen in such a way that the quantity of active product desired is applied in 1,000 liters of water / hectare, respectively. After three weeks, the degree of damage of the plants is evaluated in% of damages compared to the development of the untreated control.
Represent: 0% = no effect (same as untreated controls). 100% = total destruction. In this test they show, for example, the compounds according to the preparation examples 3, 4, 6, 9, 10, 12, 13, 17, 19, 20, 22, 24, 25, 26, 27, 28, 29, 30 , 31, 32, 33, 34, 35, 38, 40, 43, 57 and 59 with a partially good compatibility with crop plants, such as, for example, cotton, barley, corn, rapeseed, sunflower, soybeans, wheat and sugar beet, a potent effect against weeds.
I heard or cp O (l
TABLE A: PrelpOte / in erpartero test Table A-l: Active product as exemplified by Amount applied Sunflower Cotton Bro- Echino- Lo- Matrí- Xan-obtain n * (gaL ha) mus peras chloa lium caria tMum
60 20 95 95 90 90 90 90
(3)
ro h-1 cp or Cp n
Table A-2. Active product -egt d mplo Cjtitkted applied Cotton Bromus Cype- Lo- Poa Cheno- GaHn- Mabri- Sina- obtaining nß (g aLta) ras lium podium soga caria pfe
250 95 100 95 95 95 95 95 100
(4)
t cp or p o p
Table A-3. Active product according to example Quantity applied Cotton Bromua Poa Ambrosia Datura Gallium- S-teüaria of n * (g ai./ha) 125 0 95 95 90 90 90 95
(6)
to t cp or cp O cp
Table A-4. Active product for example Amount apportioned Bromos Poa GaKnsoga Matr aria Sinapis Xanthim de obtenón p ° (ai ha) 125 95 95 95 95 90 95
(9)
to cp or cp or p
Table A-5. Active product according to example Amount of consumption Beet Bromos Cyperus PE »Preparation synapse n * (g aL / ba) sugar 125 90 90 90 90
(10)
to t Cn O Cp O Cp
Table A- ^. Active product according to example Applied quantity Alope- Bro- Pañi- Foa Anrapmthps Am- Gaita- Sola- de obtenón n ° (ai ha) faces mus cum brosia soga mun
125 95 95 95 95 95 95 95 95
(12)
to to cp or Cp or Cp
Table A-7. Active product according to example applied quantity Ceba- Trigo Sunflower Alope- Cype- Ama- Porto- Sobuium of obtain n ° (ai, / ha) gives cures rus ranthus laca
125 95 95 95 95 95
(13)
t to Cp or p or Cn
Table A-8 Active product according to example Amount ap-fcada Cotton ALopc-Bro- Poa Amaran- Ga- Matri- Sola- of obtaining n ° (g aL / Jia) cures mus thus lium caria man 250 95 95 95 95 95 95 95
(17) 250 95 95 95 95 95 95
(twenty)
to t in or Cp in
Table A-9 Active product according to example Amount applied Cotton Atope- Bro- Poa Amarantbus Gamim Matri- Sobnam obtaining nß (ai. Ha) euros mus caria
125 95 95 95 95 95 95 95
125 0 95 90 95 90 90 90
to to cp or cp or to
Table A-10 Active product according to example Amount applied Wheat Beet Alope- Sorghum Galiupt Gafln- Matri- Portu- of obtaining n ° (ai./ha) sugar bowl cures rope caria laca
125 95 90 95 95 95 95
(19)
to t in or Cp O Cp
Tama A-ll Active product according to example Quantity applied Wheat Rape Cotton Agropyron Cyno-Ama- Gafin- Matri-obtaining n ° (g ai ha) don ranthus soga caria
10 0 90 95 90 95 95
(24)
t to en or Cp Cn
Table A-13 Active product according to example Amount applied Coba Agropyron Poa Giatium GaUmoga Matricaria of obtained n ° ig ai. ha) 30 90 95 95 95 95
(26)
to to Cp or en in
Table A-14. Active product (example) Fungicity, corn, Rapeseed, Soya, Cotton, Ainbrosia, Gaffiom GaJnsoga Matrix of obtaining n ° (gai.ha) 125 0 90 90 95 95
(27)
t t i- »cp or cp o in
Table A- 16. Active product according to example Quantity applied Cotton Cynodon Poa Amaraatiias GaHnsoga Sob-tram obtaining n ° (g ai./ha) 125 95 90 90 90 90 (31)
to t in en or cp
Table A-17. Active product according to example Applied cit. Trigo Cotton Gaünßoga Portulaca SteBaria of obtaining n ° (g ai./ha) 125 10 95 90 90
(32)
NJ ro in or cp or in
Table A-18. Active product according to the example applied to it Cotton Agro-Avena Bro- Lo- Ama- Ga- Sola- from g. N (g aL / ha) pyron fatua mus lium ranthus Bmn num 125 95 95 95 95 95 95 95
(3.1) 60 95 95 95 95 95 95 90
04)
t to t-1 cp or Cp or in
Table A-19. Active product according to example Quantity applied Cotton Agropyron Avena Lolium Setaria Amaraathos Ma rkaria of obtaining n ° (g ai./ha) f tua
125 95 95 95 95 95 95
(35)
t in or in or in
Table A-20. Active product according to example Quantity applied Wheat Something- Alope- Bro- Lo- Se- Ama- Cas- Sola- Vero- of gain n "(g aL / ha) don euros mus litan taria rapthus sia manna 30 100 100 100 100 100 100 95
(3 «) 125 100 100 100100 100 100 100 100
-CP. ° w? JvNv. < or o 0 OR CH. (40)
to t cp or Cp O Cp
Table A-21. Active product according to example Amount api-each Wheat barley Cotton Alope- Digi- Anta- Matri- Sola- Vero- of obtaining nß (g ai / ha) curus taria ranthus caria num nica
10 95 95 100 100 100 100
(43)
t t \ > in or in or in
Table A-22, Active product according to example Quantity Applied Wheat EcMno-Sor-Ama-Cheno- Matri- Sola- Vero- Viola de obtenón n ° (g aiJha) chloa ghum rantbus podium caria num nka
60 95 95 100 95 95 90 100
(57)
to to cp or en in
Table A-23. Active product according to example Applied Quantity Wheat Echino-Sor-Ama-Cheno- Matri- Sola- Vero- Viola de obtenón n ° (g aL ha) chloa ghum ranthus podium caria num nfca
125 95 80 100 100 100 100
(59)
Example B
Post-emergence trial
Solvent: 5 parts by weight of acetone.
Emulsifier: 1 Part by weight of alkylaryl polyglycol ether.
To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent, the amount of emulsifier indicated is added and the concentrate is diluted with water to the desired concentration. Test plants, having a height of 5 to 15 cm, are sprayed with the preparation of the active product in such a way that the desired quantities of active compound per unit area are respectively applied. The concentration of the sprayable broths is chosen in such a way that it is applied in 1,000 liters of water / ha to the desired amount in each case of active product. After three weeks, the degree of damage of the plants is evaluated in% of damages compared to the development of the untreated controls.
They mean:
0% = no effect (same as untreated controls).
100% = total destruction.
In this test, for example, the compounds according to Preparation Examples 1, 3, 6, 9, 10, 11, 17, 19, 20, 22, 34, 43, 53, 54, 55 and 59 show a compatibility broadly good against crop plants, such as, for example, cotton, wheat and sugar beet, a potent effect against weeds.
t I-1 to in cp or cp
TABLE B: Test Table B-1: Produced active according to example Quantity applied Eccino-Pañi-Ama-Cheno-Sola-Viola obtaining n * (al.ha) girl cum ranthin podium nam
60 90 90 100 100 90 95 90
(3)
to t i- * in or Cp in
Table B2. Active product according to example Amount of quantity Ed to eddoa Pan um Cassia Galium Solanum of obtendsn a * (g ai ha)
60 95 100 95 95 95
(6)
t t in or cp or in
Table B-3. Active product according to the example Quantity applied Wheat Amaranthus Cassia Sobtaum de obtenón n ° (g aUha)
60 95 100 80
(I)
to t I-1 n o n o n o n
Table B-4. Active product according to example Quantity applied Digitaria P-uticum Amarantbus Cassb Matricaria Solanum of obtaining n ° (g aiJha)
60 90 100 95 100 95 95
(9)
ro ro in or in or in
Table B-S. Produced active according to the quantity Quantity applied Wheat Digitarb E? Inc ^ of gain n ° (ga / ha)
60 80 95 90 95 80
(10)
to ro in or Cp or cp
Table B-o. Produced active according to example Quantity applied Wheat Digitaria Echüjaochloa Setaria Amaraníhus Solamun Stellaiia de obtenón n ° (g aiJha)
10 80 90 95 95 90
(M)
t ro cp or Cp or Cn
Table B-7. Active product according to example Quantity applied Wheat Removal Alo-Seta-Ama-Cheno- Do- Gßfiura of obtaining n ° (aL / ha) sugar-cane pecurus taria ranthus podium tura
125 20 80 95 90 90 95 or
(17)
to to in or in or in
Table B-8. Active product according to example Quantity applied Wheat Soak Ato- Seta- Amo- Cheno- Da- GaJ one of obtaining n ° (g aL ba) sugar bowl pecurus taña ranthus podium tura
125 10 90 90 95 95 95
(19)
t [NJ on or in or on
Table B-9. Active product according to example Applied quantity Avena fatua Ainaranütus Cassia Solanum Steuaria de obtenón n ° (g ai./ha)
125 80 1200 100 100 100
(twenty)
t ro H1 cp or cp O in
Tama B-10. Produced active according to example Amount applied AJopecunts Cypans Echlnochloa Abutilon Amaranüiuj Datura de obtenón n ° (g ai-Tha)
60 90 90 90 90 95 90
(22)
ro to H cp or in O in
Table B-ll. Active product according to example Amount applied Cotton Amaran bus Galinm SteQatia de obtenón n * (g aL ba)
60 20 95 90 90
(3. 4)
ro t t- > cp or Cp or Cn
Table B-12. Active product according to example Amount apikada Trigo Amarantiius Matrkaria Stdtaxia V of obtaining n ° (g ai./ha)
70 10 100 100 100 95
(43)
t to en or en or cp
Table B-15. Active product according to example Amount apikada Wheat Abutilon An? Rantiius Mati & aria Veranea Xanthium de obtenón n ° (g ai./ba)
60 15 95 100 95 95 95
(59)
Example C
Test with Podosphaera (apple tree) / protector
Solvent: 47 parts by weight of acetone
Emulsifier: 3 parts by weight of alkylaryl polyglycol ether. To obtain a suitable active product preparation, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test the protective activity, young plants are sprayed with the preparation of active compound in the indicated application amount. After the spray coating has dried, the plants are inoculated with an aqueous suspension of the apple fungi pathogen Podosphaera leucotr ± cha. The plants are then placed in the greenhouse at about 23 ° C and at a relative humidity of about 70%. The evaluation is carried out 10 days after the inoculation. In this case O 15% means a degree of activity that corresponds to that of untreated controls, while a degree of activity of 100% means that no attack is observed. In this test, for example, the compounds according to Preparation Examples 3, 24, 26, 29 and 30 show, with an application amount of, respectively, 100 g / hr, and an activity level of 85% up to 100%.
TABLE C Test with Podosphaera (apple tree) / protector TABLE C (Continued) Test with Podosphaera (apple tree) / protector
Table C Test with Podosphaera (apple tree) / protector
Emplo D
Test with Pyricularia (rice) / systemic
Solvent: 2.5 parts by weight of acetone
Emulsifier: 0.06 parts by weight of alkylaryl polyglycol ether. To obtain a suitable active product preparation, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
To test the systemic properties, 40 ml of the preparation of active product is produced on unitary soil, in which young rice plants have been grown. After 7 days from the treatment, the plants are inoculated with an aqueous suspension of Pyricularia oryzae. Then the plants remain in a greenhouse at a temperature of 25 ° C and with a relative humidity - of 100% air until the evaluation.
The evaluation of the attack for the disease is carried out 4 days after the inoculation. In this case 0% means a degree of activity that corresponds to that of the controls, while a degree of activity of 100% means that no attack is observed. '
In this test they show, for example, the compounds according to the preparation examples 1, 2, 3, 4, 9, 10, 11, 13, 14, 18, 21, 22, 26 and 34 with an application amount of respectively, 2 mg / 100 cm2, a degree of activity between 70% and 100%.
TABLE D Assay with Pyricularia (rice) / systemic TABLE D (Continued) Assay with Pyricularia (rice) / systemic
TABLE D (Continued) Test with Pyricularia (rice) / systemic
TABLE D (Continued) Test with Pyricularia (rice) / systemic
TABLE D (Continued) Test with Pyriculinaria (rice) / systemic
TABLE D (Continued) Test with Pyriculinaria (rice) / systemic
TABLE D (Continued) Test with Pyriculinaria (rice) / systemic
Example E.
Test with Pyricularia (rice) / resistance induction
Solvent: 2.5 parts by weight of acetone
Emulsifier: 0.06 parts by weight of alkylaryl polyglycol ether.
To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent and the concentrate is diluted with water and with the indicated amount of emulsifier to the desired concentration.
To test the resistance-inducing activity 10 young rice plants are sprayed with the preparation of the active product with the indicated application amount. After 5 days, from the treatment, the plants are inoculated with an aqueous spore suspension of Pyricularia oryzae. The plants are then placed in a greenhouse with a relative humidity of 100% and at a temperature of 25 ° C. After 4 days from the inoculation the evaluation is carried out. In this case O% means a degree of activity, which corresponds to that of the controls, while a degree of activity of 100% means that no attack is observed. In this test, for example, the compounds according to Preparation Examples 1, 2, 3, 4, 9, 10, 11, 13, 14, 18, 21, 22, 26 and 34 show, with an application amount of , respectively, 375 g / ha, a degree of activity between 80% and 100%.
Table E Test with Pyricularia (rice) / induction of resistance
Table E Test with Pyricularia (rice) / resistance induction
Table E Test with Pyricularia (rice) / resistance induction
Table E (Continued) Test with Pyricularia (rice) / resistance induction
Table E (Continued) Test with Pyricularia (rice) / resistance induction
Table E (Continued) Test with Pyricularia (rice) / resistance induction
Table E (Continued) Test with Pyricularia (rice) / resistance induction
It is noted that in relation to this date, the best method known by the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention. Having described the invention as above, the content of the following is claimed as property.
Claims (9)
1. Compound of the general formula (I) Q1 R = ((i) R " characterized in that Q1 represents oxygen or sulfur, Q2 represents oxygen or sulfur, R represents hydrogen, amino, alkylidenamino or represents a radical, optionally substituted respectively, of the series consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylamino, dialkylamino , alkanoylamino, cycloalkyl, cycloalkylalkyl, cycloalkylamino, aryl and arylalkyl, R represents alkenyl substituted if appropriate and R represents a radical, respectively substituted, if appropriate, of the series consisting of alkyl, aralkyl, aryl and heteroaryl, as well as salts of the compounds of the formula (I).
2. Compound of the general formula (I) according to claim 1, characterized in that, it represents hydrogen, amino, alkylidenamino with 1 to 6 carbon atoms, represents alkyl with 1 to 6 carbon atoms, optionally substituted by fluorine, chlorine, by bromine, by cyano, by alkoxy with 1 to 4 carbon atoms, by alkylcarbonyl with 1 to 4 carbon atoms or by alkoxycarbonyl with 1 to 4 carbon atoms, represents alkenyl with 2 to 6 carbon atoms or alkynyl with 2 to 6 carbon atoms, respectively substituted, if appropriate, by fluorine, chlorine and / or bromine, represents alkyloxy with 1 to 6 carbon atoms or alkenyloxy with 2 to 6 carbon atoms, represents alkylamino with 1 to 6 atoms of carbon, di- (C 1 -C 4 -alkyl) -amino or alkyl-carbonylamino with 1 to 4 carbon atoms, optionally substituted respectively by fluorine and / or by chlorine, represents cycloalkyl with 3 to 6 carbon atoms or cycloalkylalkyl c on 3 to 6 carbon atoms-alkyl having 1 to 4 carbon atoms substituted, where appropriate, by fluorine, chlorine, bromine and / or alkyl having 1 to 4 carbon atoms, or represents phenyl or phenyl-alkyl having 1 to 4 carbon atoms, respectively substituted, if appropriate, by fluorine, chlorine, bromine, cyano, nitro, alkyl with 1 to 4 carbon atoms, trifluoromethyl, alkoxy with 1 to 4 carbon atoms and / or by alkoxycarbonyl having 1 to 4 carbon atoms. Rz represents alkenyl having 2 to 6 carbon atoms, optionally substituted by cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, alkoxy with 1 to 4 carbon atoms or by alkoxy-carbonyl with 1 to 4 carbon atoms , R- represents the grouping where R4 and R5 are the same or different and represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, alkyl having 1 to 6 carbon atoms, which is optionally substituted by fluorine, chlorine, bromine, cyano, by carboxy, by alkoxycarbonyl with 1 to 4 carbon atoms, by alkylaminocarbonyl with 1 to 4 carbon atoms, by di- (alkyl with 1 to 4 carbon atoms) -aminocarbonyl, by alkoxy with 1 to 4 atoms of carbon, by alkyl-carbonyloxy with 1 to 4 carbon atoms, by alkoxy-carbonyloxy with 1 to 4 carbon atoms, by alkylamino-carbonyloxy with 1 to 4 carbon atoms, by alkylthio with 1 to 4 carbon atoms, alkylsulfinyl having 1 to 4 carbon atoms, alkylsulfonyl having 1 to 4 carbon atoms, di- (C1-C4 alkyl) -aminosulfonyl, cycloalkyl having 3 to 6 carbon atoms or phenyl) represents alkenyl with 2 to 6 carbon atoms (which is optionally substituted by fluorine, by chlorine, by bromine, p or cyano, by alkoxycarbonyl having 1 to 4 carbon atoms or by phenyl), represents alkynyl with 2 to 6 carbon atoms (which is optionally substituted by fluorine, chlorine, bromine, cyano, alkoxycarbonyl having 1 to 4 carbon atoms or by phenyl), represents alkoxy with 1 to 4 carbon atoms (which is optionally substituted by fluorine, chlorine, bromine, cyano, alkoxycarbonyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by alkylthio with 1 to 4 carbon atoms, by alkylsulfinyl with 1 to 4 carbon atoms, by alkylsulfonyl with 1 to 4 carbon atoms or by cycloalkyl with 3 to 6 carbon atoms), represents alkylthio with 1 to 4 carbon atoms (which is optionally substituted by fluorine / chlorine, bromine, cyano, by alkoxycarbonyl with 1 to 4 carbon atoms, by alkylthio with 1 to 4 carbon atoms, by alkylsulfinyl with 1 to 4 carbon atoms or by alkylsulfonyl with 1 to 4 carbon atoms), represents alkenyloxy with 2 to 6 atoms of carbon (which is optionally substituted by fluorine, chlorine, bromine, cyano or alkoxycarbonyl having 1 to 4 carbon atoms), represents alkenylthio having 2 to 6 carbon atoms (which is optionally substituted by fluorine, by chlorine, by bromine, by cyano, by nitro, by alkylthio with 1 to 3 carbon atoms or by alkoxy-carbonyl with 1 to 4 carbon atoms), represents alkynyloxy with 3 to 6 carbon atoms, alkynylthio with 3 to 6 carbon atoms or represents the radical -S (0) p-R6, where the numbers 1 or 2, and R represents alkyl with 1 to 4 carbon atoms (which is optionally substituted by fluorine, chlorine, bromine, cyano or alkoxycarbonyl having 1 to 4 carbon atoms), represents alkenyl with 3 to 6 carbon atoms, alkynyl with 3 to 6 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkylamino with 1 to 4 carbon atoms, alkylamino with 1 to 4 atoms carbon, di- (C1-C4 alkyl) -amino, phenyl or represents the radical -NH0R7, where R7 represents alkyl with 1 to 12 carbon atoms (Which is optionally substituted by fluorine, by chlorine by cyano, by alkoxy with 1 to 4 carbon atoms, by alkylthio with 1 to 4 carbon atoms, by alkylsulfinyl with 1 to 4 carbon atoms, by alkylsulfonyl with 1 to 4 carbon atoms, by alkylcarbonyl with 1 to 4 carbon atoms, by alkoxycarbonyl with 1 to 4 carbon atoms, by alkylaminocarbonyl with 1 to 4 carbon atoms or by di- (alkyl with 1 to 4 carbon atoms) carbon atoms) -aminocarbonyl represents alkenyl with 3 to 6 carbon atoms (which is optionally substituted by fluorine, chlorine or bromine), represents alkynyl with 3 to 6 carbon atoms, cycloalkyl with 3 to 6 atoms of carbon, cycloalkyl with 3 to 6 carbon atoms-alkyl having 1 to 2 carbon atoms, phenylalkyl with 1 to 2 carbon atoms (which is optionally substituted by fluorine, chlorine, nitro, cyano, alkyl) with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms or by alkoxycarbon with 4 carbon atoms), represents diphenylmethyl or represents phenyl (which is optionally substituted by fluorine, by chlorine, by nitro, by cyano, by alkyl with 1 to 4 carbon atoms, by trifluoromethyl, by alkoxy with 1 at 4 carbon atoms, by fluoroalkoxy with 1 to 2 carbon atoms, by alkylthio with 1 to 4 carbon atoms, by trifluoromethyl or by alkoxycarbonyl with 1 to 4 carbon atoms), in addition R4 and / or R5 represent phenyl or phenoxy , represent alkyl-carbonylamino with 1 to 4 carbon atoms, alkoxy-carbonylamino with 1 to 4 carbon atoms, alkylaminocarbonyl-amino with 1 to 4 carbon atoms, di- (alkyl with 1 to 4 carbon atoms) -amino- carbonylamino, or represent the radical -CO-R8, where R8 represents hydrogen, alkyl with 1 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, alkoxy with 1 to 6 carbon atoms, cycloalkoxy with 3 to 6 carbon atoms, carbon, alkenyloxy with 3 to 6 carbon atoms, alkylthio with 1 to 4 carbon atoms, alkylamino with 1 to 4 carbon atoms, alkoxyamino with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms-alkylamino with 1 to 4 carbon atoms or di- (alkyl with 1 to 4 carbon atoms) -amino (which are optionally substituted by fluorine and / or by chlorine), in addition R4 and / or R5 represent trimethylsilyl, diazolinyl, 1, 2, 4-oxadiazol-5-yl, 3-methyl-1 , 2,4-oxadiazol-5-yl, 1, 3-dioxolan-2-yl, alkylsulfonyloxy with 1 to 4 carbon atoms, di- (alkyl with 1 to 4 carbon atoms) - to inosulfonylamino or represent the radical -CH = N-R9, where R9 represents alkyl having from 1 to 6 carbon atoms optionally substituted by fluorine, by chlorine, by cyano, by carboxy, by alkoxy with 1 to 4 carbon atoms, by alkylthio with 1 to 4 carbon atoms, by alkylsulfinyl with 1 to 4 carbon atoms or by alkylsulfonyl with 1 to 4 carbon atoms, represents benzyl optionally substituted by fluorine or by chlorine, represents alkenyl with 3 to 6 carbon atoms or alkynyl with 3 a 6 carbon atoms optionally substituted by fluorine or chlorine, represents phenyl optionally substituted by fluorine, by chlorine; by bromine, by alkyl with 1 to 4 carbon atoms, by alkoxy with 1 to 4 carbon atoms, by trifluoromethyl, by trifluoromethoxy or by trifluoromethylthio, represents alkoxy with 1 to 6 carbon atoms, alkenyloxy with 3 to 6 carbon atoms, carbon, alkynyloxy with 3 to 6 carbon atoms or benzyloxy, optionally substituted by fluorine and / or by chlorine, represents amino, alkylamino with 1 to 4 carbon atoms, di- (alkyl with 1 to 4 carbon atoms) - amino, phenylamino, alkylcarbonylamino with 1 to 4 carbon atoms, alkoxycarbonylamino with 1 to 4 carbon atoms, alkyl-sulfonylamino with 1 to 4 carbon atoms or represents phenylsulfonylamino, optionally substituted by fluorine, chlorine, bromine or for methyl. also R represents the radical where R 10 represents hydrogen or alkyl having 1 to 4 carbon atoms, R 11 and R 12 are the same or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, alkyl having 1 to 4 carbon atoms (which is substituted in fluorine and / or chlorine), alkoxy having 1 to 4 carbon atoms (which is optionally substituted by fluorine and / or chlorine), carboxy, alkoxycarbonyl having 1 to 4 carbon atoms, dimethylaminocarbonyl, alkylsulfonyl with 1 to 4 carbon atoms or di- (alkyl with 1 to 4 carbon atoms) - aminosulfonyl. R- represents also the radical where R 13 R 14 are the same or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, alkyl having 1 to 4 carbon atoms (which is optionally substituted by fluorine and / or chlorine) or alkoxy with 1 to 4 carbon atoms (which is optionally substituted by fluorine and / or by chlorine). R ^ represents also the radical where R 15 and R 16 are the same or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, alkyl having 1 to 4 carbon atoms, (which is optionally substituted by fluorine and / or chlorine), alkoxy with 1 to 4 carbon atoms (which is optionally substituted by fluorine and / or by chlorine), represents alkylthio having 1 to 4 carbon atoms, alkylsulfinyl having 1 to 4 carbon atoms or alkylsulfonyl having 1 to 4 carbon atoms ( which are optionally substituted by fluorine and / or by chlorine), represents aminosulfonyl, mono- (alkyl having 1 to 4 carbon atoms) -aminosulfonyl, represents di- (alkyl having 1 to 4 carbon atoms) -aminosulfonyl or alkoxycarbonyl with 1 to 4 carbon atoms or dimethylaminocarbonyl). R; also represents the radical where R, 1x7 'and R 18 are the same different and represent hydrogen, fluorine, chlorine, bromine, alkyl having 1 to 4 carbon atoms (which is optionally substituted by fluorine and / or bromine), alkoxy with 1 to 4 carbon atoms (which is optionally substituted by fluorine and / or by chlorine), represents alkylthio having 1 to 4 carbon atoms, alkylsulfinyl having 1 to 4 carbon atoms or alkylsulfonyl having 1 to 4 carbon atoms (which are substituted) optionally fluorine and / or chlorine), or represents di- (alkyl having 1 to 4 carbon atoms) -aminosulfonyl; R represents also the radical where R 19 and R, 2¿0? they are the same or different and represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, alkyl having 1 to 4 carbon atoms (which is optionally substituted by fluorine and / or chlorine), alkoxy with 1 to 4 carbon atoms (which is optionally substituted by fluorine and / or by chlorine), alkylthio having 1 to 4 carbon atoms, alkylsulfinyl having 1 to 4 carbon atoms or alkylsulfonyl having 1 to 4 carbon atoms (which are optionally substituted by fluorine and / or chlorine), di- (C 1 -C 4 -alkyl) - aminosulfonyl, alkoxycarbonyl with 1 to 4 carbon atoms or dimethylaminocarbonyl, and represents oxygen, sulfur or the NT group, where it represents hydrogen, alkyl having 1 to 4 carbon atoms (which is optionally substituted by fluorine, chlorine, bromine or cyan), cycloalkyl having 3 to 6 carbon atoms, benzyl, phenyl (which is optionally substituted by fluorine, chlorine, bromine or nitro), alkylcarbonyl with 1 to 4 atoms carbon, alkoxycarbonyl with 1 to 4 carbon atoms or di- (alkyl with 1 to 4 carbon atoms) -aminocarbonyl; R- represents also the radical where R21 and R22 are the same or different and represent hydrogen, alkyl having 1 to 4 carbon atoms, halogen, alkoxy-carbonyl with 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms . Y1 represents sulfur or the grouping N-R23, where R 23 represents hydrogen or alkyl with 1 to 4 carbon atoms; R3 also represents the radical where R 24 represents hydrogen, alkyl having 1 to 4 carbon atoms, benzyl, pyridyl, quinolinyl or phenyl, R 25 represents hydrogen, halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms (which is optionally substituted by fluorine and or chlorine), alkoxy with 1 to 4 carbon atoms (which is optionally substituted by fluorine and / or chlorine), dioxolanyl or alkoxycarbonyl with 1 to 4 carbon atoms and R 26 represents hydrogen, halogen or I rent with 1 to 4 carbon atoms; as well as its salts are sodium, potassium, magnesium, calcium, ammonium, dialkylammonium with 1 to 4 carbon atoms, di- (alkyl with 1 to 4 carbon atoms) -ammonium, tri- ( alkyl with 1 to 4 carbon atoms) -ammonium, tetra- (C 1 -C 4) alkyl-ammonium, tri- (C 1 -C 4) alkyl- sulfonyl, cycloalkyl-ammonium with 5 to 4 carbon atoms) or 6 carbon and di- (C 1 -C 2 -alkyl) -benzyl-ammonium atoms of the compounds of the formula (I).
3. Compounds of the formula (I) according to claims 1 or 2, characterized in that, in the same R1 represents methyl, ethyl, n- or i-propyl respectively substituted, respectively, by fluorine, by chlorine, by cyano, by methoxy or by ethoxy, represents propenyl, butenyl, propynyl or butynyl substituted, where appropriate, by fluorine, chlorine or bromine, represents methoxy, ethoxy, n- or i-propoxy or represents allyloxy, represents methylamino, ethylamino, n- or i-propylamino , dimethylamino or diethylamino, or represents cyclopropyl optionally substituted by fluorine, chlorine, bromine, methyl or ethyl. R 2 represents ethenyl, propenyl or butenyl substituted respectively by cyano, fluorine, chlorine and / or bromine and R 3 represents the radical where R 4 represents fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, • n- or i-propoxy, difluoromethoxy, trifluoromethoxy, 2-chloro-ethoxy, 2-fluoro-ethoxy, 2, 2-di-fluoro-ethoxy, 2,2,2-trifluoro-ethoxy, 1,1,2,2-tetrafluoro-ethoxy, 1, 1, 2,2,2-pentafluoroethoxy, 2-methoxy-ethoxy, cyclopropylmethoxy , methylthio, ethylthio, n- or i- propylthio, 2-fluoro-ethylthio, allyloxy, propargyloxy, methylsulphinyl, ethylsulfonyl, methylsulfonyl, ethylsulfonyl, dimethylaminosulfonyl, diethylaminosul fonyl, N-methoxy-N-methylaminosulfonyl, phenyl, phenoxy, methoxycarbonyl, ethoxycarbonyl , n- or i- propoxycarbonyl and R5 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio or ethylthio; R3 also represents the radical where R 10 represents hydrogen, R 11 represents fluorine, chlorine, bromine, methyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyl or dimethylaminosulfonyl, R 12 represents hydrogen; R3 also represents the radical where R represents methyl, ethyl, n- or i-propyl or R3 further represents the radical where R24 represents methyl, ethyl, n- or i-propyl, phenyl or pyridyl, R25 represents hydrogen, fluorine, chlorine or bromine and R26 represents fluorine, chlorine, bromine, methoxycarbonyl or ethoxycarbonyl.
4. Process for obtaining compounds of the formula (I) according to one of claims 1 to 3, characterized in that (a) triazolin (ti) onas of the general formula (II) are reacted ai) in which Q1, R1 and R2 have the meaning indicated above in one of claims 1 to 3, with sulfonyl iso (thio) cyanates of the. General Formula (III) R -S02-N = C (III) wherein Q2 and R3 have the meaning indicated above in claims 1 to 3, if appropriate in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent, or because b) derivatives are reacted of triazolin (ti) ona of the general formula (IV) wherein Q1 QZ r R1 and R2 have the meaning indicated above and Z represents halogen, alkoxy, aralkoxy or aryloxy, with sulfonamides of the general formula (V) R-S02-NH2 (V) wherein R3 has the meaning indicated above, optionally in the presence of an acid acceptor and, if appropriate, in the presence of a diluent, or in that (c) triazolin (ti) -ones of the general formula are reacted ( II) wherein Q1, R1 and R2 have the meaning indicated above, with sulfonamide derivatives of the general formula (VI) R3-S02-NH-CQ2-Z (VI) wherein Q2 and R3 have the meaning indicated above and Z represents halogen, alkoxy, aralkoxy or aryloxy, if appropriate in the presence of an acid acceptor and, if appropriate, in the presence of a diluent, or because (d) they react triazolin (ti) onas of the general formula (II) wherein Q1, R1 and R2 have the meaning indicated above, with sulfonyl halides of the general formula (VII) R3-S02-X (VII) in which R3 has the meaning indicated above and X represents halogen, and (thio) metal cyanates of the general formula (VIII) MQ -CN (VIII) where Q2 has the meaning indicated above and M represents an alkali metal or equivalent of alkaline earth metal, in the given case in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent, and, if appropriate, the compounds obtained according to the procedures (a) , (b), (c) or (d) of the formula (I), are transformed into salts according to usual methods.
5. Herbicidal and fungicidal compositions, characterized in that it has a content in at least one compound of the formula (I) according to one of the claims 1 to 3.
6. Use of the compounds of the general formula (I) according to one of claims 1 to 3, for the control of the undesirable growth of plants and / or pathogenic fungi for plants.
7. Method for controlling weeds and / or pathogenic fungi for plants, characterized in that the compounds of the general formula (I) according to one of claims 1 to 3 are allowed to act on the weeds or on the fungi or about its environment.
8. Process for the preparation of herbicidal and fungicidal compositions, characterized in that compounds of the general formula are mixed (I) according to one of claims 1 to 3, with extenders and / or surfactants.
9. Compounds of the general formula (XIV) wherein R1 R2 and Q1 have the meanings indicated in claims 1 to 3 and A represents hydrogen or the group -CQ2-Z, where Q2 has the meaning indicated in claim 1 and Z represents halogen, alkoxy, aralkoxy or aryloxy. SUMMARY OF THE INVENTION The invention relates to novel sulfonylamino (thio) carbonyltriazolin (ti) onas with alkenyl substituents of the general formula (I) characterized in that Q1 represents oxygen or sulfur, Q2 represents oxygen or sulfur, R1 represents hydrogen, amino, alkylidenamino or represents a radical, optionally substituted respectively, of the series consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylamino, dialkylamino allylamino, cycloalkyl, cycloalkylalkyl, cycloalkylamino, aryl and arylalkyl, R2 represents substituted alkenyl and R3 represents a radical, respectively substituted, if appropriate, of the series consisting of alkyl, aralkyl, aryl and heteroaryl, and salts of the compounds of the formula (I), and processes and new intermediates for the preparation of the compound (I) and their uses as herbicides and / or fungicides.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19823131.8 | 1998-05-23 |
Publications (1)
Publication Number | Publication Date |
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MXPA00011410A true MXPA00011410A (en) | 2001-09-07 |
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