JP3330155B2 - Hydrazone-based compounds, methods for their production, intermediates for their production, and pesticides containing them - Google Patents
Hydrazone-based compounds, methods for their production, intermediates for their production, and pesticides containing themInfo
- Publication number
- JP3330155B2 JP3330155B2 JP07940292A JP7940292A JP3330155B2 JP 3330155 B2 JP3330155 B2 JP 3330155B2 JP 07940292 A JP07940292 A JP 07940292A JP 7940292 A JP7940292 A JP 7940292A JP 3330155 B2 JP3330155 B2 JP 3330155B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- halogen atom
- alkyl group
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims description 124
- 150000007857 hydrazones Chemical class 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 9
- 239000000575 pesticide Substances 0.000 title description 10
- 239000000543 intermediate Substances 0.000 title 1
- 125000005843 halogen group Chemical group 0.000 claims description 73
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 54
- -1 4-tert-butylphenyl Chemical group 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 35
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 15
- 241000607479 Yersinia pestis Species 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 12
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 12
- 230000000361 pesticidal effect Effects 0.000 claims description 11
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
- DFZSWUNQVNVQFT-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-[4-(trifluoromethyl)phenyl]ethanone Chemical compound C1=CC(F)=CC=C1C(=O)CC1=CC=C(C(F)(F)F)C=C1 DFZSWUNQVNVQFT-UHFFFAOYSA-N 0.000 claims description 5
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims 4
- 241001024304 Mino Species 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 description 94
- 239000002904 solvent Substances 0.000 description 54
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 238000012360 testing method Methods 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- 230000035484 reaction time Effects 0.000 description 12
- 125000000547 substituted alkyl group Chemical group 0.000 description 11
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 238000010898 silica gel chromatography Methods 0.000 description 10
- 125000005017 substituted alkenyl group Chemical group 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 241000238631 Hexapoda Species 0.000 description 9
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 9
- 150000008282 halocarbons Chemical class 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 7
- 125000004093 cyano group Chemical group *C#N 0.000 description 7
- 125000003107 substituted aryl group Chemical group 0.000 description 7
- 241000254173 Coleoptera Species 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000003377 acid catalyst Substances 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 230000000749 insecticidal effect Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000002798 polar solvent Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 125000005415 substituted alkoxy group Chemical group 0.000 description 5
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 5
- NSGPGRDZOPPVMQ-UHFFFAOYSA-N 1-fluoro-4-[2-[4-(trifluoromethyl)phenyl]ethenyl]benzene Chemical compound C1=CC(F)=CC=C1C=CC1=CC=C(C(F)(F)F)C=C1 NSGPGRDZOPPVMQ-UHFFFAOYSA-N 0.000 description 4
- XWHIYFBWVUQTHQ-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-1-(4-fluorophenyl)ethanone Chemical compound C1=CC(C(C)(C)C)=CC=C1CC(=O)C1=CC=C(F)C=C1 XWHIYFBWVUQTHQ-UHFFFAOYSA-N 0.000 description 4
- 239000005995 Aluminium silicate Substances 0.000 description 4
- 241000237858 Gastropoda Species 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 241001454295 Tetranychidae Species 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 235000012211 aluminium silicate Nutrition 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 125000004426 substituted alkynyl group Chemical group 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- MEQWGTBCTHCERR-UHFFFAOYSA-N 1,2-bis(4-chlorophenyl)ethanone Chemical compound C1=CC(Cl)=CC=C1CC(=O)C1=CC=C(Cl)C=C1 MEQWGTBCTHCERR-UHFFFAOYSA-N 0.000 description 3
- NGIMSHKDYBQSLC-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-1-(4-chlorophenyl)ethanone Chemical compound C1=CC(C(C)(C)C)=CC=C1CC(=O)C1=CC=C(Cl)C=C1 NGIMSHKDYBQSLC-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000238876 Acari Species 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241001414720 Cicadellidae Species 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000895 acaricidal effect Effects 0.000 description 3
- 239000000642 acaricide Substances 0.000 description 3
- 239000000440 bentonite Substances 0.000 description 3
- 229910000278 bentonite Inorganic materials 0.000 description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 235000013312 flour Nutrition 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 235000015243 ice cream Nutrition 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000005645 nematicide Substances 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 230000003071 parasitic effect Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- FBZVZUSVGKOWHG-UHFFFAOYSA-N 1,1-dimethoxy-n,n-dimethylethanamine Chemical compound COC(C)(OC)N(C)C FBZVZUSVGKOWHG-UHFFFAOYSA-N 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- XTUUQKUKKDAQMT-UHFFFAOYSA-N 1,2-bis(4-chlorophenyl)ethylidenehydrazine Chemical compound C=1C=C(Cl)C=CC=1C(=NN)CC1=CC=C(Cl)C=C1 XTUUQKUKKDAQMT-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
- DIPLXSBTYRDLGV-UHFFFAOYSA-N 2-methyl-2-methylsulfanylpropanal Chemical compound CSC(C)(C)C=O DIPLXSBTYRDLGV-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 241000289763 Dasygaster padockina Species 0.000 description 2
- 241000258937 Hemiptera Species 0.000 description 2
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 241001149911 Isopoda Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 241000244206 Nematoda Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 241000985245 Spodoptera litura Species 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 2
- AWYFNIZYMPNGAI-UHFFFAOYSA-L ethylenebis(dithiocarbamate) Chemical compound [S-]C(=S)NCCNC([S-])=S AWYFNIZYMPNGAI-UHFFFAOYSA-L 0.000 description 2
- YREQHYQNNWYQCJ-UHFFFAOYSA-N etofenprox Chemical compound C1=CC(OCC)=CC=C1C(C)(C)COCC1=CC=CC(OC=2C=CC=CC=2)=C1 YREQHYQNNWYQCJ-UHFFFAOYSA-N 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 150000004045 organic chlorine compounds Chemical class 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- LLMLSUSAKZVFOA-UJURSFKZSA-N (1S,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@@H]1C(O)=O LLMLSUSAKZVFOA-UJURSFKZSA-N 0.000 description 1
- SPVZAYWHHVLPBN-UJURSFKZSA-N (1s,3r)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@@H](C=C(Cl)C(F)(F)F)[C@@H]1C(O)=O SPVZAYWHHVLPBN-UJURSFKZSA-N 0.000 description 1
- YOSCIBHNIINXGQ-UHFFFAOYSA-N (2,2-dimethyl-3H-1-benzofuran-7-yl) N-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2.CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 YOSCIBHNIINXGQ-UHFFFAOYSA-N 0.000 description 1
- DOBUSJIVSSJEDA-UHFFFAOYSA-L 1,3-dioxa-2$l^{6}-thia-4-mercuracyclobutane 2,2-dioxide Chemical compound [Hg+2].[O-]S([O-])(=O)=O DOBUSJIVSSJEDA-UHFFFAOYSA-L 0.000 description 1
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
- VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 description 1
- SWHRDLPFZQFSLS-UHFFFAOYSA-N 1-[(6-chloropyridin-3-yl)methyl]-2-methyl-3-nitroguanidine Chemical compound [O-][N+](=O)N=C(NC)NCC1=CC=C(Cl)N=C1 SWHRDLPFZQFSLS-UHFFFAOYSA-N 0.000 description 1
- PZKQVCIFNVONNY-UHFFFAOYSA-N 1-[1,2-bis(4-chlorophenyl)ethylideneamino]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)NN=C(C=1C=CC(Cl)=CC=1)CC1=CC=C(Cl)C=C1 PZKQVCIFNVONNY-UHFFFAOYSA-N 0.000 description 1
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 1
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
- NXFSILLOHOWXSD-UHFFFAOYSA-N 1-n'-[(6-chloropyridin-3-yl)methyl]-1-n,1-n'-dimethyl-2-nitroethene-1,1-diamine Chemical group [O-][N+](=O)C=C(NC)N(C)CC1=CC=C(Cl)N=C1 NXFSILLOHOWXSD-UHFFFAOYSA-N 0.000 description 1
- UCYJAEIKGXUDAM-UHFFFAOYSA-N 1-n-[(6-chloropyridin-3-yl)methyl]-1-n',1-n'-dimethyl-2-nitroethene-1,1-diamine Chemical group [O-][N+](=O)C=C(N(C)C)NCC1=CC=C(Cl)N=C1 UCYJAEIKGXUDAM-UHFFFAOYSA-N 0.000 description 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- OJDLYYQCXMCLPJ-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-1-phenylethanone Chemical compound C1=CC(C(C)(C)C)=CC=C1CC(=O)C1=CC=CC=C1 OJDLYYQCXMCLPJ-UHFFFAOYSA-N 0.000 description 1
- QKJPXROEIJPNHG-UHFFFAOYSA-N 2-(4-tert-butylphenyl)acetonitrile Chemical compound CC(C)(C)C1=CC=C(CC#N)C=C1 QKJPXROEIJPNHG-UHFFFAOYSA-N 0.000 description 1
- NRKRPOHWHYCORO-UHFFFAOYSA-N 2-[(6-chloropyridin-3-yl)methyl]-1,1-dimethyl-3-nitroguanidine Chemical compound [O-][N+](=O)N=C(N(C)C)NCC1=CC=C(Cl)N=C1 NRKRPOHWHYCORO-UHFFFAOYSA-N 0.000 description 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical class NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- DSHWWPMOLSFNCS-UHFFFAOYSA-N 2-chloro-5-[[2-(2-ethylsulfanyl-1-nitroethylidene)imidazolidin-1-yl]methyl]pyridine Chemical compound CCSCC([N+]([O-])=O)=C1NCCN1CC1=CC=C(Cl)N=C1 DSHWWPMOLSFNCS-UHFFFAOYSA-N 0.000 description 1
- ALNDHUQPXHHNON-UHFFFAOYSA-N 2-chloro-5-[[2-(nitromethylidene)imidazolidin-1-yl]methyl]pyridine Chemical compound [O-][N+](=O)C=C1NCCN1CC1=CC=C(Cl)N=C1 ALNDHUQPXHHNON-UHFFFAOYSA-N 0.000 description 1
- ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- QMVSVDPAWIVPNR-UHFFFAOYSA-N 3,7,11-trimethyldodeca-2,4-dienoic acid Chemical compound CC(C)CCCC(C)CC=CC(C)=CC(O)=O QMVSVDPAWIVPNR-UHFFFAOYSA-N 0.000 description 1
- MQBGNZBSQKLFQG-UHFFFAOYSA-N 3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl-1-[(2,3,5,6-tetrafluoro-4-methylphenyl)methyl]cyclopropane-1-carboxylic acid Chemical compound FC1=C(F)C(C)=C(F)C(F)=C1CC1(C(O)=O)C(C)(C)C1C=C(Cl)C(F)(F)F MQBGNZBSQKLFQG-UHFFFAOYSA-N 0.000 description 1
- FSCWZHGZWWDELK-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione Chemical compound O=C1C(C)(C=C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 FSCWZHGZWWDELK-UHFFFAOYSA-N 0.000 description 1
- YWOWJQMFMXHLQD-UHFFFAOYSA-N 3-(trifluoromethyl)pyridin-2-amine Chemical compound NC1=NC=CC=C1C(F)(F)F YWOWJQMFMXHLQD-UHFFFAOYSA-N 0.000 description 1
- ZTLMFNYACJYRIS-UHFFFAOYSA-N 3-[(6-chloropyridin-3-yl)methyl]-2-(nitromethylidene)-1,3-thiazolidine Chemical compound [O-][N+](=O)C=C1SCCN1CC1=CC=C(Cl)N=C1 ZTLMFNYACJYRIS-UHFFFAOYSA-N 0.000 description 1
- VBIUHODDMHFHOV-UHFFFAOYSA-N 3-dihydroxyphosphinothioyl-1,3-thiazolidin-2-one Chemical compound OP(O)(=S)N1CCSC1=O VBIUHODDMHFHOV-UHFFFAOYSA-N 0.000 description 1
- NMWKWBPNKPGATC-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2-benzofuran-1(3H)-one Chemical compound ClC1=C(Cl)C(Cl)=C2COC(=O)C2=C1Cl NMWKWBPNKPGATC-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-HOSYLAQJSA-N 4-chlorobenzaldehyde Chemical group ClC1=CC=C([13CH]=O)C=C1 AVPYQKSLYISFPO-HOSYLAQJSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- WQKHERPPDYPMNX-UHFFFAOYSA-N 6-chloro-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(Cl)=CC=C21 WQKHERPPDYPMNX-UHFFFAOYSA-N 0.000 description 1
- 239000005660 Abamectin Substances 0.000 description 1
- 206010063409 Acarodermatitis Diseases 0.000 description 1
- 241000254032 Acrididae Species 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000272525 Anas platyrhynchos Species 0.000 description 1
- 241000256186 Anopheles <genus> Species 0.000 description 1
- 241000142094 Anopheles lindesayi japonicus Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- KPBRVLOUGYZBJC-UHFFFAOYSA-N CCCC1OC(CN2C=CC=C2)(C(C=CC(Cl)=C2)=C2Cl)OC1 Chemical class CCCC1OC(CN2C=CC=C2)(C(C=CC(Cl)=C2)=C2Cl)OC1 KPBRVLOUGYZBJC-UHFFFAOYSA-N 0.000 description 1
- 241001672694 Citrus reticulata Species 0.000 description 1
- KFOBXDFJLPCKDZ-UHFFFAOYSA-N ClC1=C(C(=C(C=C1)S(=O)(=O)C1=C(C(=C(C=C1)Cl)Cl)Cl)Cl)Cl Chemical compound ClC1=C(C(=C(C=C1)S(=O)(=O)C1=C(C(=C(C=C1)Cl)Cl)Cl)Cl)Cl KFOBXDFJLPCKDZ-UHFFFAOYSA-N 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 241000256059 Culex pipiens Species 0.000 description 1
- 241001635274 Cydia pomonella Species 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- AIGRXSNSLVJMEA-UHFFFAOYSA-N EPN Chemical compound C=1C=CC=CC=1P(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 AIGRXSNSLVJMEA-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 241001466042 Fulgoromorpha Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 239000005906 Imidacloprid Substances 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 241000256602 Isoptera Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 241000131077 Lucanidae Species 0.000 description 1
- 241000721696 Lymantria Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 241001477931 Mythimna unipuncta Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 241000320508 Pentatomidae Species 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- 229910052777 Praseodymium Inorganic materials 0.000 description 1
- 241000238711 Pyroglyphidae Species 0.000 description 1
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 1
- 241000700141 Rotifera Species 0.000 description 1
- 241000447727 Scabies Species 0.000 description 1
- 241000254062 Scarabaeidae Species 0.000 description 1
- 241000545593 Scolytinae Species 0.000 description 1
- 241000258242 Siphonaptera Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920000142 Sodium polycarboxylate Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241001481659 Syrphidae Species 0.000 description 1
- 241000270666 Testudines Species 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 1
- 241001414989 Thysanoptera Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- JARYYMUOCXVXNK-UHFFFAOYSA-N Validamycin A Natural products OC1C(O)C(OC2C(C(O)C(O)C(CO)O2)O)C(CO)CC1NC1C=C(CO)C(O)C(O)C1O JARYYMUOCXVXNK-UHFFFAOYSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- MPPVRGVVCRVJEE-UHFFFAOYSA-N [1-(4-fluorophenyl)-2-[4-(trifluoromethyl)phenyl]ethylidene]hydrazine Chemical compound C=1C=C(F)C=CC=1C(=NN)CC1=CC=C(C(F)(F)F)C=C1 MPPVRGVVCRVJEE-UHFFFAOYSA-N 0.000 description 1
- ULVYOEDMMZYWKK-UHFFFAOYSA-N [2-(4-tert-butylphenyl)-1-(4-chlorophenyl)ethylidene]hydrazine Chemical compound C1=CC(C(C)(C)C)=CC=C1CC(=NN)C1=CC=C(Cl)C=C1 ULVYOEDMMZYWKK-UHFFFAOYSA-N 0.000 description 1
- YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QXAITBQSYVNQDR-UHFFFAOYSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1N=CN(C)C=NC1=CC=C(C)C=C1C QXAITBQSYVNQDR-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical class C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 235000020289 caffè mocha Nutrition 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- STUSTWKEFDQFFZ-KPKJPENVSA-N chlordimeform Chemical compound CN(C)\C=N\C1=CC=C(Cl)C=C1C STUSTWKEFDQFFZ-KPKJPENVSA-N 0.000 description 1
- UISUNVFOGSJSKD-UHFFFAOYSA-N chlorfluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=NC=C(C(F)(F)F)C=C1Cl UISUNVFOGSJSKD-UHFFFAOYSA-N 0.000 description 1
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
- HRBKVYFZANMGRE-UHFFFAOYSA-N chlorpyrifos-methyl Chemical compound COP(=S)(OC)OC1=NC(Cl)=C(Cl)C=C1Cl HRBKVYFZANMGRE-UHFFFAOYSA-N 0.000 description 1
- JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical class [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical class C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 150000008056 dicarboxyimides Chemical class 0.000 description 1
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
- UWQMKVBQKFHLCE-UHFFFAOYSA-N diclomezine Chemical compound C1=C(Cl)C(C)=C(Cl)C=C1C1=NNC(=O)C=C1 UWQMKVBQKFHLCE-UHFFFAOYSA-N 0.000 description 1
- UOAMTSKGCBMZTC-UHFFFAOYSA-N dicofol Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 UOAMTSKGCBMZTC-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 description 1
- NHFDKKSSQWCEES-UHFFFAOYSA-N dihydrogen phosphate;tris(2-hydroxyethyl)azanium Chemical compound OP(O)(O)=O.OCCN(CCO)CCO NHFDKKSSQWCEES-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000004656 dimethylamines Chemical class 0.000 description 1
- DWLVWMUCHSLGSU-UHFFFAOYSA-N dimethylcarbamic acid Chemical compound CN(C)C(O)=O DWLVWMUCHSLGSU-UHFFFAOYSA-N 0.000 description 1
- MZGNSEAPZQGJRB-UHFFFAOYSA-N dimethyldithiocarbamic acid Chemical compound CN(C)C(S)=S MZGNSEAPZQGJRB-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- AWZOLILCOUMRDG-UHFFFAOYSA-N edifenphos Chemical compound C=1C=CC=CC=1SP(=O)(OCC)SC1=CC=CC=C1 AWZOLILCOUMRDG-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- DWRKFAJEBUWTQM-UHFFFAOYSA-N etaconazole Chemical compound O1C(CC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 DWRKFAJEBUWTQM-UHFFFAOYSA-N 0.000 description 1
- JHUCCRNKXWBDTO-UHFFFAOYSA-N ethoxy(propylsulfanyl)phosphinic acid Chemical compound CCCSP(O)(=O)OCC JHUCCRNKXWBDTO-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- HOXINJBQVZWYGZ-UHFFFAOYSA-N fenbutatin oxide Chemical compound C=1C=CC=CC=1C(C)(C)C[Sn](O[Sn](CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C1=CC=CC=C1 HOXINJBQVZWYGZ-UHFFFAOYSA-N 0.000 description 1
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 1
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 1
- 229960002089 ferrous chloride Drugs 0.000 description 1
- 235000013360 fish flour Nutrition 0.000 description 1
- PTCGDEVVHUXTMP-UHFFFAOYSA-N flutolanil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 PTCGDEVVHUXTMP-UHFFFAOYSA-N 0.000 description 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 229940046533 house dust mites Drugs 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 229940056881 imidacloprid Drugs 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 description 1
- 230000000366 juvenile effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
- HWSZZLVAJGOAAY-UHFFFAOYSA-L lead(II) chloride Chemical compound Cl[Pb]Cl HWSZZLVAJGOAAY-UHFFFAOYSA-L 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 229940074994 mercuric sulfate Drugs 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical class [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 1
- 229910000372 mercury(II) sulfate Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- FXWHFKOXMBTCMP-WMEDONTMSA-N milbemycin Natural products COC1C2OCC3=C/C=C/C(C)CC(=CCC4CC(CC5(O4)OC(C)C(C)C(OC(=O)C(C)CC(C)C)C5O)OC(=O)C(C=C1C)C23O)C FXWHFKOXMBTCMP-WMEDONTMSA-N 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- VXWICDYXLQABPY-UHFFFAOYSA-N n-[(6-chloropyridin-3-yl)methyl]-1,3-dimethyl-5-nitro-2,4-dihydropyrimidin-6-amine Chemical compound C1N(C)CN(C)C(NCC=2C=NC(Cl)=CC=2)=C1[N+]([O-])=O VXWICDYXLQABPY-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-UHFFFAOYSA-N n-[4-chloro-2-(trifluoromethyl)phenyl]-1-imidazol-1-yl-2-propoxyethanimine Chemical compound C1=CN=CN1C(COCCC)=NC1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UGLPZZZYSRHEJD-UHFFFAOYSA-N n-carbamoyl-3,5-dichlorobenzamide Chemical compound NC(=O)NC(=O)C1=CC(Cl)=CC(Cl)=C1 UGLPZZZYSRHEJD-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- DSOOGBGKEWZRIH-UHFFFAOYSA-N nereistoxin Chemical class CN(C)C1CSSC1 DSOOGBGKEWZRIH-UHFFFAOYSA-N 0.000 description 1
- CFRPSFYHXJZSBI-UHFFFAOYSA-N nitenpyram Chemical group [O-][N+](=O)C=C(NC)N(CC)CC1=CC=C(Cl)N=C1 CFRPSFYHXJZSBI-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- FITIWKDOCAUBQD-UHFFFAOYSA-N prothiofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(Cl)C=C1Cl FITIWKDOCAUBQD-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical class C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 208000005687 scabies Diseases 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003450 sulfenic acids Chemical class 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- QLEGUFMFYFDAJZ-UHFFFAOYSA-M triphenyl-[[4-(trifluoromethyl)phenyl]methyl]phosphanium;chloride Chemical compound [Cl-].C1=CC(C(F)(F)F)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 QLEGUFMFYFDAJZ-UHFFFAOYSA-M 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
【0001】[0001]
【産業上の利用分野】本発明は、後記一般式(I)で表
わされるヒドラゾン系化合物、それらの製造方法及びそ
れらの製造用中間体並びに後記一般式(IX)で表わさ
れるヒドラゾン系化合物を含有する有害生物防除剤及び
それらの有効量を施用する有害生物防除方法に関する。The present invention relates to a hydrazone compound represented by the following general formula (I), a method for producing them, an intermediate for producing them, and a hydrazone compound represented by the following general formula (IX). The present invention relates to a pesticidal agent and a pesticidal method for applying an effective amount thereof.
【0002】[0002]
【従来の技術】ヒドラゾン系化合物は例えば、特公昭5
0−16410号、特開昭54−122261、同56
−45452、同63−93761、特開平2−138
246各公報などに記載されている。しかしながらそこ
には後記一般式(I)で表わされる本発明化合物は開示
されていない。2. Description of the Related Art Hydrazone compounds are disclosed in, for example,
No. 0-16410, JP-A-5-122261, JP-A-56
-45452, 63-93761, JP-A-2-138
246 publications. However, there is no disclosure of the compound of the present invention represented by the following general formula (I).
【0003】[0003]
【発明の開示】本発明は、一般式(I):DISCLOSURE OF THE INVENTION The present invention provides a compound of the general formula (I):
【0004】[0004]
【化18】 (式中、R1、R2及びR4は各々独立して、水素原
子、ハロゲン原子、ニトロ基、シアノ基、水酸基、トリ
アルキルシリル基、置換されてもよいアルキル基、置換
されてもよいシクロアルキル基、置換されてもよいアル
コキシ基、置換されてもよいアルキルチオ基、置換され
てもよいカルボキシル基、置換されてもよいアリール基
又は置換されてもよいアリールオキシ基であり、R3は
水素原子、ハロゲン原子、ニトロ基、シアノ基、水酸
基、置換されてもよいアルキル基、置換されてもよいシ
クロアルキル基、置換されてもよいアルコキシ基、置換
されてもよいアルキルチオ基、置換されてもよいカルボ
キシル基、X1SO2NH−基、X2CO2−基、X3
SO−基、X4SO2−基、X5SO3−基、又は(X
6Y1)2P(=Y2)Y3−基であり、R5及びR6
は各々独立して水素原子、置換されてもよいアルキル
基、X7CO−基、X8OCO−基、X9SO2−基、
置換されてもよいカルバモイル基、置換されてもよいア
ルケニル基、置換されてもよいアルキニル基、或は置換
されてもよいヘテロアリール基であるか又はR5とR6
が一緒になって、=CR7R8基を形成してもよく、X
1、X2、X3、X4、X5、X8及びX9は各々独立
して、置換されてもよいアルキル基、置換されてもよい
アルコキシ基、置換されてもよいアルケニル基又は置換
されてもよいアリール基であり、X6は置換されてもよ
いアルキル基、置換されてもよいアルケニル基又は置換
されてもよいアリール基であり、X7は水素原子、置換
されてもよいアルキル基、置換されてもよいアルケニル
基又は置換されてもよいアリール基であり、Y1、Y2
及びY3は各々独立して酸素原子又は硫黄原子であり、
R7及びR8は各々独立して水素原子、置換されてもよ
いアルキル基、置換されてもよいシクロアルキル基、置
換されてもよいアルコキシ基、置換されてもよいアルケ
ニル基、置換されてもよいアリール基、置換されてもよ
いアミノ基又は置換されてもよい環状アミノ基である。
但し、各置換基が以下の(1)〜(10)である場合を
除く。(1)R3及びR4が同時に水素原子である場
合、(2)R5及びR6の少くとも1つが無置換のカル
バモイル基である場合、(3)R1、R2、R3及びR
4の少くとも1つがニトロ基である場合、(4)R2、
R4及びR5が水素原子であり、R6がエトキシカルボ
ニル基であり、かつR1及びR3の少くとも1つがp−
メトキシ基である場合、(5)R1、R2、R4及びR
5が水素原子であり、R3がp−ターシャリーブチル基
であり、かつR6がエトキシカルボニル基である場合、
(6)R1、R2及びR4が水素原子であり、R3がp
−弗素原子であり、R5がイソプロピル基であり、かつ
R6が水素原子又はアセチル基である場合、(7)
R1、R2、R4、R5及びR6が水素原子であり、か
つR3がp−塩素原子である場合、(8)R7が無置換
フェニル基であり、かつR8が置換されてもよいベンジ
ル基である場合、(9)R1、R2及びR3がメトキシ
基であり、R4が水素原子であり、かつR5及びR6が
メチル基である場合、(10)R5が水素原子で、かつ
R6が置換されてもよいフェニルスルホニル基である場
合。)で表わされるヒドラゾン系化合物又はそれらの
塩、それらの製造方法及び一般式(II−5):Embedded image (Wherein R 1 , R 2 and R 4 are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a trialkylsilyl group, an optionally substituted alkyl group, or an optionally substituted R 3 is a cycloalkyl group, an optionally substituted alkoxy group, an optionally substituted alkylthio group, an optionally substituted carboxyl group, an optionally substituted aryl group or an optionally substituted aryloxy group; Hydrogen atom, halogen atom, nitro group, cyano group, hydroxyl group, optionally substituted alkyl group, optionally substituted cycloalkyl group, optionally substituted alkoxy group, optionally substituted alkylthio group, substituted Carboxyl group, X 1 SO 2 NH— group, X 2 CO 2 — group, X 3
An SO— group, an X 4 SO 2 — group, an X 5 SO 3 — group, or (X
6 Y 1 ) 2 P (= Y 2 ) Y 3 —, and R 5 and R 6
Are each independently a hydrogen atom, an alkyl group which may be substituted, an X 7 CO- group, an X 8 OCO- group, an X 9 SO 2 -group,
An optionally substituted carbamoyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, or an optionally substituted heteroaryl group, or R 5 and R 6
May together form a = CR 7 R 8 group,
1 , X 2 , X 3 , X 4 , X 5 , X 8 and X 9 are each independently an alkyl group which may be substituted, an alkoxy group which may be substituted, an alkenyl group which may be substituted or substituted. X 6 is an optionally substituted alkyl group, an optionally substituted alkenyl group or an optionally substituted aryl group, and X 7 is a hydrogen atom, an optionally substituted alkyl group. Group, an optionally substituted alkenyl group or an optionally substituted aryl group, Y 1 , Y 2
And Y 3 are each independently an oxygen atom or a sulfur atom;
R 7 and R 8 are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkoxy group, an optionally substituted alkenyl group, an optionally substituted A good aryl group, an optionally substituted amino group or an optionally substituted cyclic amino group.
However, the case where each substituent is the following (1) to (10) is excluded. (1) when R 3 and R 4 are simultaneously hydrogen atoms, (2) when at least one of R 5 and R 6 is an unsubstituted carbamoyl group, (3) R 1 , R 2 , R 3 and R
When at least one of 4 is a nitro group, (4) R 2 ,
R 4 and R 5 are hydrogen atoms, R 6 is an ethoxycarbonyl group, and at least one of R 1 and R 3 is p-
When it is a methoxy group, (5) R 1 , R 2 , R 4 and R
5 is a hydrogen atom, R 3 is a p-tert-butyl group, and R 6 is an ethoxycarbonyl group;
(6) R 1 , R 2 and R 4 are hydrogen atoms, and R 3 is p
(7) when R 5 is an isopropyl group and R 6 is a hydrogen atom or an acetyl group,
When R 1 , R 2 , R 4 , R 5 and R 6 are a hydrogen atom and R 3 is a p-chlorine atom, (8) R 7 is an unsubstituted phenyl group and R 8 is substituted (9) When R 1 , R 2 and R 3 are methoxy groups, R 4 is a hydrogen atom, and R 5 and R 6 are methyl groups, (10) A) when R 5 is a hydrogen atom and R 6 is a phenylsulfonyl group which may be substituted; A) a hydrazone-based compound or a salt thereof, a production method thereof, and a general formula (II-5):
【0005】[0005]
【化19】 (式中、R12、R13、R14及びR15は各々独立
して水素原子、ハロゲン原子又はハロゲン原子で置換さ
れてもよいアルキル基である。但し、各置換基が以下の
(1)〜(4)である場合を除く。(1)R12、R
13、R14及びR15が各々独立して水素原子又はハ
ロゲン原子である場合、(2)R12又はR13がp−
CF3基で、かつR14又はR15がp−CF3基であ
る場合、(3)R12又はR13がハロゲン原子で、か
つR14又はR15がメチル基、エチル基又はプロピル
基である場合、(4)R12又はR13がメチル基、エ
チル基又はプロピル基であり、かつR14又はR15が
ハロゲン原子である場合。)で表わされる中間体に関す
る。また本発明は、一般式(IX):Embedded image (Wherein, R 12 , R 13 , R 14 and R 15 are each independently a hydrogen atom, a halogen atom or an alkyl group optionally substituted with a halogen atom. However, each substituent is represented by the following (1) (1) R 12 , R
When R 13 and R 14 and R 15 are each independently a hydrogen atom or a halogen atom, (2) R 12 or R 13 is p-
When the group is CF 3 and R 14 or R 15 is a p-CF 3 group, (3) R 12 or R 13 is a halogen atom, and R 14 or R 15 is a methyl group, an ethyl group or a propyl group. In some cases, (4) when R 12 or R 13 is a methyl group, an ethyl group or a propyl group, and R 14 or R 15 is a halogen atom. )). The present invention also provides a compound of the general formula (IX):
【0006】[0006]
【化20】 (式中、R1、R2、R3、R4、R5及びR6は前述
の通りである。但し、R3及びR4が同時に水素原子で
ある場合を除く。)で表わされるヒドラゾン系化合物又
はそれらの塩を含有することを特徴とする有害生物防除
剤及びそれらの有効量を施用することを特徴とする有害
生物防除方法に関する。前記一般式(I)及び(IX)
に含まれる置換されてもよいアルキル基、置換されても
よいアルコキシ基、置換されてもよいアルキルチオ基、
置換されてもよいアルケニル基及び置換されてもよいア
ルキニル基の置換基としては、ハロゲン原子;ハロゲン
原子で置換されてもよいアルコキシ基;ハロゲン原子で
置換されてもよいアルキル基或はハロゲン原子で置換さ
れてもよいフェニル基;ハロゲン原子で置換されてもよ
いアルキル基或はハロゲン原子で置換されてもよいフェ
ノキシ基;シアノ基;アルキルアミノ基;又はアルコキ
シカルボニル基などが挙げられ、置換されてもよいカル
ボキシル基とはカルボキシル基中の水素原子が他の置換
基で置換されたものであって、その置換基としては、ハ
ロゲン原子で置換されてもよいアルキル基;又はハロゲ
ン原子で置換されてもよいアルキル基或はハロゲン原子
で置換されてもよいアリール基などが挙げられる。ま
た、置換されてもよいヘテロアリール基、置換されても
よいアリール基、置換されてもよいアリールオキシ基及
び置換されてもよいシクロアルキル基の置換基として
は、ハロゲン原子;ハロゲン原子で置換されてもよいア
ルコキシ基;ハロゲン原子で置換されてもよいアルキル
基;ハロゲン原子で置換されてもよいアルキル基或はハ
ロゲン原子で置換されてもよいフェニル基;ハロゲン原
子で置換されてもよいアルキル基或はハロゲン原子で置
換されてもよいフェノキシ基;シアノ基;アルキルアミ
ノ基;又はアルコキシカルボニル基などが挙げられ、置
換されてもよいカルバモイル基、置換されてもよいアミ
ノ基及び置換されてもよい環状アミノ基の置換基として
は、ハロゲン原子で置換されてもよいアルコキシ基;ハ
ロゲン原子で置換されてもよいアルキル基;ハロゲン原
子で置換されてもよいアルキル基或はハロゲン原子で置
換されてもよいフェニル基;ハロゲン原子で置換されて
もよいアルキル基或はハロゲン原子で置換されてもよい
フェノキシ基;シアノ基;アルキルアミノ基;又はアル
コキシカルボニル基などが挙げられる。これら置換基の
数は1又は2以上であり、またこれら置換基におけるハ
ロゲン原子、アルキル基、ハロゲン置換アルキル基及び
ハロゲン置換アルキルのハロゲン原子の数も1又は2以
上であり、それらの数が2以上の場合はそれらは同一で
あっても異なってもよい。Embedded image (Wherein, R 1 , R 2 , R 3 , R 4 , R 5, and R 6 are as described above, except that R 3 and R 4 are simultaneously hydrogen atoms.) The present invention relates to a pesticidal agent characterized by containing a system compound or a salt thereof and a pesticidal method characterized by applying an effective amount thereof. The general formulas (I) and (IX)
An optionally substituted alkyl group, an optionally substituted alkoxy group, an optionally substituted alkylthio group,
Examples of the substituent of the optionally substituted alkenyl group and the optionally substituted alkynyl group include a halogen atom; an alkoxy group optionally substituted with a halogen atom; an alkyl group optionally substituted with a halogen atom or a halogen atom. A phenyl group which may be substituted; an alkyl group which may be substituted with a halogen atom or a phenoxy group which may be substituted with a halogen atom; a cyano group; an alkylamino group; or an alkoxycarbonyl group. The carboxyl group may be a group in which a hydrogen atom in the carboxyl group is substituted with another substituent, and the substituent may be an alkyl group which may be substituted with a halogen atom; And an aryl group which may be substituted with a halogen atom. Examples of the substituent of the optionally substituted heteroaryl group, the optionally substituted aryl group, the optionally substituted aryloxy group and the optionally substituted cycloalkyl group include a halogen atom; An alkoxy group which may be substituted with a halogen atom; an alkyl group which may be substituted with a halogen atom or a phenyl group which may be substituted with a halogen atom; an alkyl group which may be substituted with a halogen atom Or a phenoxy group which may be substituted with a halogen atom; a cyano group; an alkylamino group; or an alkoxycarbonyl group, and the like, and which may be a carbamoyl group, an amino group which may be substituted, and As the substituent for the cyclic amino group, an alkoxy group which may be substituted with a halogen atom; An alkyl group which may be substituted; an alkyl group which may be substituted with a halogen atom or a phenyl group which may be substituted with a halogen atom; an alkyl group which may be substituted with a halogen atom or may be substituted with a halogen atom A phenoxy group; a cyano group; an alkylamino group; or an alkoxycarbonyl group. The number of these substituents is 1 or 2 or more, and the number of halogen atoms, alkyl group, halogen-substituted alkyl group and halogen atom of halogen-substituted alkyl in these substituents is 1 or 2 or more. In the above case, they may be the same or different.
【0007】一般式(I)、(II−5)及び(IX)
に含まれるアルキル基又はアルキル部分としては炭素数
1〜6のもの、例えばメチル基、エチル基、プロピル
基、ブチル基、ペンチル基、ヘキシル基などが挙げら
れ、アルケニル基又はアルケニル部分としては炭素数2
〜6のもの、例えばビニル基、プロペニル基、ブテニル
基、ペンテニル基、ヘキセニル基などが挙げられ、アル
キニル基又はアルキニル部分としては炭素数2〜6のも
の、例えばエチニル基、プロピニル基、ブチニル基、ペ
ンチニル基、ヘキシニル基などが挙げられ、上記各基又
は各部分は直鎖又は枝分れ脂肪鎖の構造異性のものも含
む。また一般式(I)及び(IX)に含まれるシクロア
ルキル基又はシクロアルキル部分としては炭素数3〜6
のもの、例えばシクロプロピル基、シクロブチル基、シ
クロペンチル基、シクロヘキシル基が挙げられる。一般
式(I)及び(IX)に含まれるアリール基としては例
えばフェニル基、ナフチル基などが挙げられ、ヘテロア
リール基としては例えばフリル基、チエニル基、ピリジ
ル基などが挙げられる。一般式(I)及び(IX)に含
まれる環状アミノ基としては−N=(CH2)n(式
中、nは2〜7の整数である)が挙げられる。一般式
(I)及び(IX)に含まれるハロゲン原子としては、
例えば弗素原子、塩素原子、臭素原子、沃素原子が挙げ
られる。Formulas (I), (II-5) and (IX)
Examples of the alkyl group or alkyl moiety contained therein include those having 1 to 6 carbon atoms, such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group. 2
To 6, such as a vinyl group, a propenyl group, a butenyl group, a pentenyl group, a hexenyl group, and the like. Examples thereof include a pentynyl group and a hexynyl group, and the above-mentioned groups or parts also include those having a linear or branched aliphatic chain with structural isomerism. The cycloalkyl group or cycloalkyl moiety contained in the general formulas (I) and (IX) has 3 to 6 carbon atoms.
For example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. Examples of the aryl group included in formulas (I) and (IX) include a phenyl group and a naphthyl group, and examples of the heteroaryl group include a furyl group, a thienyl group, and a pyridyl group. Examples of the cyclic amino group contained in the general formulas (I) and (IX) include -N = (CH 2 ) n (where n is an integer of 2 to 7). As the halogen atom contained in the general formulas (I) and (IX),
Examples include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
【0008】一般式(I)及び(IX)で表わされる化
合物の中で望ましい態様について下記する。 (1)R1、R2及びR4が各々独立して、水素原子、
ハロゲン原子、置換されてもよいアルキル基、置換され
てもよいアルコキシ基、置換されてもよいアルキルチオ
基又は置換されてもよいカルボキシル基である場合が望
ましく、水素原子、ハロゲン原子、置換されてもよいア
ルキル基又は置換されてもよいアルコキシ基である場合
がさらに望ましく、水素原子、ハロゲン原子、ハロゲン
原子で置換されてもよいアルキル基又はハロゲン原子で
置換されてもよいアルコキシ基である場合が最も望まし
い。 (2)R3がハロゲン原子、置換されてもよいアルキル
基、置換されてもよいアルコキシ基、置換されてもよい
アルキルチオ基、置換されてもよいカルボキシル基又は
X5SO3−基(X5が置換されてもよいアルキル基で
ある)である場合が望ましく、ハロゲン原子、置換され
てもよいアルキル基又は置換されてもよいアルコキシ基
である場合がさらに望ましく、ハロゲン原子、ハロゲン
原子で置換されてもよいアルキル基又はハロゲン原子で
置換されてもよいアルコキシ基である場合が最も望まし
い。 (3)R5及びR6が各々独立して、水素原子、置換さ
れてもよいアルキル基、X7CO−基(X7は前述の通
りである)、X8OCO−基(X8が置換されてもよい
アルキル基、置換されてもよいアルケニル基又は置換さ
れてもよいアリール基である)、置換されたカルバモイ
ル基、置換されてもよいアルケニル基、置換されてもよ
いアルキニル基、置換されてもよいヘテロアリール基又
はR5とR6が一緒になって形成される=CR7R8基
(R7及びR8が各々独立して、水素原子、置換されて
もよいアルキル基、置換されてもよいシクロアルキル
基、置換されてもよいアルコキシ基、置換されてもよい
アルケニル基又は置換されてもよいアミノ基である)で
ある場合が望ましく、水素原子、置換されてもよいアル
キル基、X7CO−基(X7が水素原子又は置換されて
もよいアルキル基である)、X8OCO−基(X8が置
換されてもよいアルキル基である)、置換されたカルバ
モイル基又はR5とR6が一緒になって形成される=C
R7R8基(R7及びR8が各々独立して、水素原子、
置換されてもよいアルキル基、置換されてもよいシクロ
アルキル基、置換されてもよいアルコキシ基又は置換さ
れてもよいアミノ基である)である場合がさらに望まし
く、R5が水素原子又はアルキル基であり、R6がX7
CO−基(X7が水素原子又はアルキル基である)又は
X8OCO−基(X8がアルキル基である)であり、R
5及びR6が一緒になって形成する=CR7R8基(R
7が水素原子又はアルキル基であり、R8がアルキル基
で置換されてもよいアミノ基又はアルコキシ基である)
である場合が最も望ましい。 (4)一般式(I)及び(IX)で表わされる化合物中
で以下の化合物が最も望ましい。〔4’−クロロ−2−
(4−トリフルオロメチルフェニル)アセトフェノン〕
N’−〔1−(ジメチルアミノ)エチリデン〕ヒドラゾ
ン、〔4’−フルオロ−2−(4−トリフルオロメチル
フェニル)アセトフェノン〕N’−〔1−(ジメチルア
ミノ)エチリデン〕ヒドラゾン、エチル3−〔1−(4
−クロロフェニル)−2−(4−トリフルオロメチルフ
ェニル)エチリデン〕カーバゼート、〔4’−クロロ−
2−(4−ターシャリーブチルフェニル)アセトフェノ
ン〕N’−〔1−(ジメチルアミノ)エチリデン〕ヒド
ラゾン又は〔4’−フルオロ−2−(4−ターシャリー
ブチルフェニル)アセトフェノン〕N’−〔1−(ジメ
チルアミノ)エチリデン〕ヒドラゾンPreferred embodiments of the compounds represented by formulas (I) and (IX) are described below. (1) R 1 , R 2 and R 4 are each independently a hydrogen atom,
It is preferably a halogen atom, an alkyl group which may be substituted, an alkoxy group which may be substituted, an alkylthio group which may be substituted or a carboxyl group which may be substituted, and a hydrogen atom, a halogen atom or a substituted More preferably, it is a good alkyl group or an optionally substituted alkoxy group, most preferably a hydrogen atom, a halogen atom, an alkyl group which may be substituted with a halogen atom or an alkoxy group which may be substituted with a halogen atom. desirable. (2) R 3 is a halogen atom, an alkyl group which may be substituted, an alkoxy group which may be substituted, an alkylthio group which may be substituted, a carboxyl group which may be substituted or an X 5 SO 3 — group (X 5 Is an alkyl group which may be substituted), more preferably a halogen atom, an alkyl group which may be substituted or an alkoxy group which may be substituted, and more preferably a halogen atom, which is substituted with a halogen atom. Most preferred is an alkyl group which may be substituted or an alkoxy group which may be substituted with a halogen atom. (3) R 5 and R 6 are each independently a hydrogen atom, an optionally substituted alkyl group, X 7 CO- group (X 7 are as defined above), X 8 OCO- group (X 8 is An optionally substituted alkyl group, an optionally substituted alkenyl group or an optionally substituted aryl group), a substituted carbamoyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, A heteroaryl group or an = CR 7 R 8 group formed by combining R 5 and R 6 (where R 7 and R 8 are each independently a hydrogen atom, an alkyl group which may be substituted, A cycloalkyl group which may be substituted, an alkoxy group which may be substituted, an alkenyl group which may be substituted or an amino group which may be substituted), and a hydrogen atom or an alkyl group which may be substituted. Group, 7 CO- group (X 7 is a hydrogen atom or an optionally substituted alkyl group), X 8 OCO- group (X 8 is an alkyl group which may be substituted), a carbamoyl group, or R 5 is substituted And R 6 are formed together = C
R 7 R 8 groups (R 7 and R 8 are each independently a hydrogen atom,
An alkyl group which may be substituted, a cycloalkyl group which may be substituted, an alkoxy group which may be substituted or an amino group which may be substituted), and R 5 is a hydrogen atom or an alkyl group. And R 6 is X 7
A CO— group (X 7 is a hydrogen atom or an alkyl group) or an X 8 OCO— group (X 8 is an alkyl group);
5 and R 6 together form a = CR 7 R 8 group (R
7 is a hydrogen atom or an alkyl group, and R 8 is an amino group or an alkoxy group which may be substituted with an alkyl group)
Is most desirable. (4) Among the compounds represented by formulas (I) and (IX), the following compounds are most desirable. [4'-chloro-2-
(4-trifluoromethylphenyl) acetophenone]
N '-[1- (dimethylamino) ethylidene] hydrazone, [4'-fluoro-2- (4-trifluoromethylphenyl) acetophenone] N'-[1- (dimethylamino) ethylidene] hydrazone, ethyl 3- [ 1- (4
-Chlorophenyl) -2- (4-trifluoromethylphenyl) ethylidene] carbazate, [4'-chloro-
2- (4-tert-butylphenyl) acetophenone] N '-[1- (dimethylamino) ethylidene] hydrazone or [4'-fluoro-2- (4-tert-butylphenylphenyl) acetophenone] N'-[1- (Dimethylamino) ethylidene] hydrazone
【0009】一般式(I)及び(IX)で表わされる化
合物は、酸性物質或は塩基性物質との塩をとりうる。そ
の酸性物質との塩としては、例えば塩酸塩、硫酸塩のよ
うな無機酸塩などが挙げられ、また塩基性物質との塩と
してはナトリウム塩、カリウム塩、カルシウム塩、アン
モニウム塩、ジメチルアミン塩などの無機塩基或は有機
塩基との塩が挙げられる。また、前記一般式(I)及び
(IX)で表わされる化合物には、ヒドラゾンの二重結
合のためE体及びZ体の幾何異性体が存在し、それらの
各異性体及び各異性体の混合物が本発明に包含される。The compounds represented by the general formulas (I) and (IX) can take a salt with an acidic substance or a basic substance. Examples of the salt with the acidic substance include inorganic salts such as hydrochloride and sulfate, and examples of the salt with the basic substance include sodium salt, potassium salt, calcium salt, ammonium salt, and dimethylamine salt. And a salt with an inorganic base or an organic base. The compounds represented by the general formulas (I) and (IX) include E-form and Z-form geometric isomers due to a hydrazone double bond, and each of these isomers and a mixture of each isomer are present. Are included in the present invention.
【0010】前記一般式(I)で表わされる化合物は例
えば次記反応工程1〜7によって製造することができ
る。The compound represented by the general formula (I) can be produced, for example, by the following reaction steps 1 to 7.
【0011】<反応工程1><Reaction step 1>
【0012】[0012]
【化21】 (式中、R1、R2、R3、R4、R5及びR6は前述
の通りである) R5及びR6が一緒になって=CR7R8基を形成する
場合Embedded image (Wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as described above) When R 5 and R 6 together form a = CR 7 R 8 group
【0013】<反応工程2><Reaction step 2>
【0014】[0014]
【化22】 (式中、R1、R2、R3、R4、R7及びR8は前述
の通りであり、J1はアルキル基である。) R5及びR6が一緒になって=CR7R8基を形成し、
かつR7及びR8が水素原子、置換されてもよいアルキ
ル基、置換されてもよいシクロアルキル基、置換されて
もよいアルケニル基又は置換されてもよいアリール基の
場合Embedded image (Wherein R 1 , R 2 , R 3 , R 4 , R 7 and R 8 are as described above, and J 1 is an alkyl group.) R 5 and R 6 are taken together to form CRCR 7 R 8 groups are formed,
And when R 7 and R 8 are a hydrogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group or an optionally substituted aryl group
【0015】<反応工程3><Reaction step 3>
【0016】[0016]
【化23】 (式中、R1、R2、R3及びR4は前述の通りであ
り、R9及びR10は各々独立して水素原子、置換され
てもよいアルキル基、置換されてもよいシクロアルキル
基、置換されてもよいアルケニル基又は置換されてもよ
いアリール基である) R5及びR6が一緒になって=CR7R8基を形成し、
かつR8が置換されてもよいアミノ基又は置換されても
よい環状アミノ基の場合Embedded image (Wherein R 1 , R 2 , R 3 and R 4 are as described above, and R 9 and R 10 are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl A group, an optionally substituted alkenyl group or an optionally substituted aryl group) R 5 and R 6 together form a = CR 7 R 8 group,
And when R 8 is an optionally substituted amino group or an optionally substituted cyclic amino group
【0017】<反応工程4><Reaction step 4>
【0018】[0018]
【化24】 (式中、R1、R2、R3、R4及びR7は前述の通り
であり、J2及びJ3は各々独立して、水素原子;ハロ
ゲン原子で置換されてもよいアルキル基;ハロゲン原子
で置換されてもよいアルコキシ基;ハロゲン原子で置換
されてもよいアルキル基或はハロゲン原子で置換されて
もよいフェニル基;ハロゲン原子で置換されてもよいア
ルキル基或はハロゲン原子で置換されてもよいフェノキ
シ基;シアノ基;アルキルアミノ基;アルコキシカルボ
ニル基又はJ2とJ3が隣接する窒素原子と一緒になっ
て置換されてもよい環状アミノ基を形成してもよい)Embedded image (Wherein R 1 , R 2 , R 3 , R 4 and R 7 are as described above, and J 2 and J 3 are each independently a hydrogen atom; an alkyl group optionally substituted by a halogen atom; An alkoxy group optionally substituted with a halogen atom; an alkyl group optionally substituted with a halogen atom or a phenyl group optionally substituted with a halogen atom; an alkyl group optionally substituted with a halogen atom or substituted with a halogen atom A phenoxy group; a cyano group; an alkylamino group; an alkoxycarbonyl group or a cyclic amino group in which J 2 and J 3 may be substituted together with an adjacent nitrogen atom.
【0019】<反応工程5><Reaction step 5>
【0020】[0020]
【化25】 (式中、R1、R2、R3、R4、R7、J2及びJ3
は前述の通りである) R6がX7CO−基、X8OCO−基又はX9SO2−
基の場合Embedded image (Wherein, R 1 , R 2 , R 3 , R 4 , R 7 , J 2 and J 3
Is the same as described above.) R 6 is an X 7 CO— group, an X 8 OCO— group or an X 9 SO 2 —.
Group
【0021】<反応工程6><Reaction step 6>
【0022】[0022]
【化26】 (式中、R1、R2、R3及びR4は前述の通りであ
り、R11は水素原子、置換されてもよいアルキル基、
X7CO−基、X8OCO−基、X9SO2−基
(X7、X8及びX9は前述の通りである)、置換され
てもよいカルバモイル基、置換されてもよいアルケニル
基、置換されてもよいアルキニル基又は置換されてもよ
いヘテロアリール基であり、J4はR11とは独立して
X7CO−基、X8OCO−基、X9SO2−基
(X7、X8及びX9は前述の通りである)である〕 R6がJ5NHCO−基(置換されてもよいカルバモイ
ル基の一部)の場合Embedded image (Wherein R 1 , R 2 , R 3 and R 4 are as described above, R 11 is a hydrogen atom, an alkyl group which may be substituted,
X 7 CO— group, X 8 OCO— group, X 9 SO 2 — group (X 7 , X 8 and X 9 are as described above), an optionally substituted carbamoyl group, an optionally substituted alkenyl group , An optionally substituted alkynyl group or an optionally substituted heteroaryl group, and J 4 is independently of R 11 , an X 7 CO— group, an X 8 OCO— group, an X 9 SO 2 — group (X 7, X 8 and X 9 are the a) defined above] when R 6 J 5 NHCO- group (part of a carbamoyl group which may be substituted)
【0023】<反応工程7><Reaction step 7>
【0024】[0024]
【化27】 (式中、R1、R2、R3、R4及びR11は前述の通
りであり、J5はハロゲン原子で置換されてもよいアル
キル基;ハロゲン原子で置換されてもよいアルキル基或
はハロゲン原子で置換されてもよいフェニル基;アルキ
ルアミノ基又はアルコキシカルボニル基である) 前記反応工程7中、一般式(I−7)で表わされる化合
物のJ5NHCO−基の水素原子は、通常のアルキル化
反応によってアルキル化することができる。また、前記
一般式(II)で表わされる化合物は例えば次記反応工
程8〜16によって製造することができる。Embedded image (Wherein R 1 , R 2 , R 3 , R 4 and R 11 are as described above, and J 5 is an alkyl group optionally substituted with a halogen atom; an alkyl group optionally substituted with a halogen atom or hydrogen atom of J 5 NHCO- group in an alkylamino group or an alkoxycarbonyl group) said reaction step 7, the compound represented by the general formula (I-7) is a halogen atom phenyl group which may be substituted by the It can be alkylated by a usual alkylation reaction. The compound represented by the general formula (II) can be produced, for example, by the following reaction steps 8 to 16.
【0025】<反応工程8><Reaction step 8>
【0026】[0026]
【化28】 (式中、R1、R2、R3及びR4は前述の通りであ
る)Embedded image (Wherein R 1 , R 2 , R 3 and R 4 are as described above)
【0027】<反応工程9><Reaction step 9>
【0028】[0028]
【化29】 (式中、R1、R2、R3及びR4は前述の通りであ
り、Halはハロゲン原子である)Embedded image (Wherein R 1 , R 2 , R 3 and R 4 are as described above, and Hal is a halogen atom)
【0029】<反応工程10><Reaction step 10>
【0030】[0030]
【化30】 (式中、R1、R2、R3、R4及びHalは前述の通
りである)Embedded image (Wherein R 1 , R 2 , R 3 , R 4 and Hal are as described above)
【0031】<反応工程11><Reaction step 11>
【0032】[0032]
【化31】 (式中、R1、R2、R3、R4及びHalは前述の通
りであり、Phはフェニル基である)Embedded image (Wherein R 1 , R 2 , R 3 , R 4 and Hal are as described above, and Ph is a phenyl group)
【0033】<反応工程12><Reaction step 12>
【0034】[0034]
【化32】 (式中、R1、R2、R3、R4、Hal及びPhは前
述の通りである)Embedded image (Wherein R 1 , R 2 , R 3 , R 4 , Hal and Ph are as described above)
【0035】<反応工程13><Reaction step 13>
【0036】[0036]
【化33】 (式中、R1、R2、R3及びR4は前述の通りであ
る) R3がX2CO2−基又はX5SO3−基の場合Embedded image (In the formula, R 1 , R 2 , R 3 and R 4 are as described above.) When R 3 is an X 2 CO 2 — group or an X 5 SO 3 — group.
【0037】<反応工程14><Reaction step 14>
【0038】[0038]
【化34】 (式中、R1、R2、R3、R4及びHalは前述の通
りであり、J6はX2CO−基又はX5SO2−基であ
る(X2及びX5は前述の通りである)〕 R3がX1SO2NH−基の場合Embedded image (Wherein, R 1 , R 2 , R 3 , R 4 and Hal are as described above, and J 6 is an X 2 CO— group or an X 5 SO 2 — group (X 2 and X 5 are as described above. When R 3 is X 1 SO 2 NH— group
【0039】<反応工程15><Reaction step 15>
【0040】[0040]
【化35】 (式中、R1、R2、R4及びX1は前述の通りであ
る) R3がX3SO−基又はX4SO2−基の場合Embedded image (In the formula, R 1 , R 2 , R 4 and X 1 are as described above.) When R 3 is an X 3 SO— group or an X 4 SO 2 — group
【0041】<反応工程16><Reaction step 16>
【0042】[0042]
【化36】 (式中、R1、R2及びR4は前述の通りであり、X
10はX3又はX4と同じであり、nは1又は2であ
る) 前記一般式(I−2)で表わされる化合物は、例えば次
記反応工程17によって製造することができる。Embedded image (Wherein R 1 , R 2 and R 4 are as described above, and X
10 is the same as X 3 or X 4 and n is 1 or 2.) The compound represented by the general formula (I-2) can be produced, for example, by the following reaction step 17.
【0043】<反応工程17> 前記一般式(VI)で表わされる化合物は、例えば次記
反応工程18によって製造することができる。<Reaction step 17> The compound represented by the general formula (VI) can be produced, for example, by the following reaction step 18.
【0044】<反応工程18><Reaction step 18>
【0045】[0045]
【化37】 (式中、R1、R2、R3、R4及びX7は前述の通り
である) 前記一般式(VIII)で表わされる化合物は、例えば
次記反応工程19によって製造することができる。Embedded image (Wherein R 1 , R 2 , R 3 , R 4 and X 7 are as described above) The compound represented by the general formula (VIII) can be produced, for example, by the following reaction step 19.
【0046】<反応工程19> (式中、R1、R2、R3、R4、R7及びX7は前述
の通りである) 前記一般式(VI)で表わされる化合物は、前記一般式
(I)で表わされる化合物又は一般式(I−2)で表わ
される化合物の製造方法によって製造することができ、
一般式(XII)で表わされる化合物及び一般式(XI
II)で表わされる化合物は前記一般式(II)で表わ
される化合物の製造方法と同様にして製造することがで
きる。また、前記一般式(IX)で表わされる化合物で
あって、前記一般式(I)で表わされる化合物の範囲外
のものについても前記方法に準じて製造することができ
る。<Reaction step 19> (Wherein R 1 , R 2 , R 3 , R 4 , R 7 and X 7 are as described above) The compound represented by the general formula (VI) is a compound represented by the general formula (I) Or can be produced by a method for producing a compound represented by the general formula (I-2),
The compound represented by the general formula (XII) and the compound represented by the general formula (XI
The compound represented by II) can be produced in the same manner as in the method for producing the compound represented by the general formula (II). Further, the compound represented by the general formula (IX), which is out of the range of the compound represented by the general formula (I), can also be produced according to the above method.
【0047】前記反応工程1,3及び17の反応は通
常、溶媒の存在下、必要により、酸触媒の存在下で行な
われ、反応温度は通常−20〜+200℃、望ましくは
−10〜+150℃であり、反応時間は通常0.1〜1
50時間である。溶媒としては、例えば、ジエチルエー
テル、テトラヒドロフラン、ジオキサンのようなエーテ
ル類;エチレングリコール、グリセリン、メタノール、
エタノールのようなアルコール類;N,N−ジメチルホ
ルムアミド、N’N−ジメチルアセトアミド、N−メチ
ル−2−ピロリドン、ジメチルスルホキシド、スルホラ
ンのような非プロトン性極性溶媒;ベンゼン、トルエ
ン、クロロベンゼンのような芳香族炭化水素類;塩化メ
チレン、クロロホルムのようなハロゲン化炭化水素類;
ペンタン、ヘキサン、ヘプタンのような脂肪族炭化水素
類;シクロヘキサンのような脂環式炭化水素類;ピリジ
ン、ピコリンのようなピリジン類;酢酸;水などが挙げ
られ、これら溶媒を混合して使用してもよい。酸触媒と
しては例えば、塩酸、硫酸、硝酸のような鉱酸;ギ酸、
酢酸、プロピオン酸、メタンスルホン酸、ベンゼンスル
ホン酸、p−トルエンスルホン酸のような有機酸;ピリ
ジン塩酸塩、トリエチルアミン塩酸塩のようなアミン類
の酸付加塩などが挙げられる。The reactions in the above reaction steps 1, 3 and 17 are usually carried out in the presence of a solvent, if necessary, in the presence of an acid catalyst. The reaction temperature is usually -20 to + 200 ° C, preferably -10 to + 150 ° C. The reaction time is usually 0.1 to 1
50 hours. Examples of the solvent include ethers such as diethyl ether, tetrahydrofuran, and dioxane; ethylene glycol, glycerin, methanol,
Alcohols such as ethanol; aprotic polar solvents such as N, N-dimethylformamide, N'N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide and sulfolane; benzene, toluene and chlorobenzene Aromatic hydrocarbons; halogenated hydrocarbons such as methylene chloride and chloroform;
Aliphatic hydrocarbons such as pentane, hexane and heptane; alicyclic hydrocarbons such as cyclohexane; pyridines such as pyridine and picoline; acetic acid; water; You may. Examples of the acid catalyst include mineral acids such as hydrochloric acid, sulfuric acid, and nitric acid; formic acid,
Organic acids such as acetic acid, propionic acid, methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid; and acid addition salts of amines such as pyridine hydrochloride and triethylamine hydrochloride.
【0048】前記反応工程2の反応は、必要により溶媒
及び/又は酸触媒の存在下で行なわれ、反応温度は通常
0〜200℃、望ましくは50〜150℃であり、反応
時間は通常0.1〜100時間である。溶媒としては例
えば、前記反応工程1、3及び17で使用されるような
エーテル類、アルコール類、非プロトン性極性溶媒、芳
香族炭化水素類、ハロゲン化炭化水素類及び水の他、ア
セトニトリルのようなニトリル類などが挙げられ、これ
ら溶媒を混合して使用してもよい。酸触媒としては例え
ば前記反応工程1、3及び17で使用されるものと同様
のものが挙げられる。The reaction in the reaction step 2 is carried out in the presence of a solvent and / or an acid catalyst, if necessary. 1 to 100 hours. Examples of the solvent include ethers, alcohols, aprotic polar solvents, aromatic hydrocarbons, halogenated hydrocarbons and water as used in the reaction steps 1, 3 and 17, and acetonitrile. Nitriles and the like, and these solvents may be mixed and used. As the acid catalyst, for example, those similar to those used in the above reaction steps 1, 3 and 17 can be mentioned.
【0049】前記反応工程4及び5の反応は必要により
溶媒の存在下で行なわれ、反応温度は通常−20〜+2
00℃、望ましくは0〜100℃であり、反応時間は通
常0.1〜100時間である。溶媒としては例えば前記
反応工程1、3及び17で使用されるような芳香族炭化
水素類、ピリジン類、ハロゲン化炭化水素類、脂肪族炭
化水素類、水などが挙げられ、これら溶媒を混合して使
用してもよい。前記反応工程6、7、14及び15の反
応は通常、溶媒の存在下、必要により、酸結合剤の存在
下で行なわれ、反応温度は通常−20〜+200℃、望
ましくは0〜150℃であり、反応時間は通常0.1〜
100時間である。溶媒としては例えば前記反応工程
1、3及び17で使用されるようなエーテル類、非プロ
トン性極性溶媒、芳香族炭化水素類、ハロゲン化炭化水
素類、脂肪族炭化水素類、脂環式炭化水素類、ピリジン
類、水、アセトニトリルのようなニトリル類などの不活
性有機溶媒が挙げられ、これら溶媒を混合して使用して
もよい。酸結合剤としては例えばトリエチルアミンのよ
うな三級アルキルアミン、炭酸ナトリウムのようなアル
カリ金属炭酸塩、ピリジンなどが挙げられる。The reactions in the above reaction steps 4 and 5 are carried out in the presence of a solvent if necessary, and the reaction temperature is usually -20 to +2.
The reaction temperature is usually 00 ° C, preferably 0 ° C to 100 ° C, and the reaction time is usually 0.1 to 100 hours. Examples of the solvent include aromatic hydrocarbons, pyridines, halogenated hydrocarbons, aliphatic hydrocarbons, water and the like as used in the above reaction steps 1, 3 and 17, and these solvents are mixed. May be used. The reactions of the reaction steps 6, 7, 14 and 15 are usually carried out in the presence of a solvent, if necessary, in the presence of an acid binder, and the reaction temperature is usually −20 to + 200 ° C., preferably 0 to 150 ° C. Yes, the reaction time is usually 0.1 to
100 hours. Examples of the solvent include ethers, aprotic polar solvents, aromatic hydrocarbons, halogenated hydrocarbons, aliphatic hydrocarbons, and alicyclic hydrocarbons as used in the above reaction steps 1, 3 and 17. , Pyridines, water, and inert organic solvents such as nitriles such as acetonitrile, and these solvents may be used as a mixture. Examples of the acid binder include tertiary alkylamines such as triethylamine, alkali metal carbonates such as sodium carbonate, and pyridine.
【0050】前記反応工程8の反応は、通常のフリーデ
ルクラフツ反応であり、溶媒及び触媒の存在下で行なわ
れ、反応温度は−20〜+200℃、望ましくは−10
〜+100℃であり、反応時間は0.1〜100時間で
ある。溶媒としては、例えば二硫化炭素、前記反応工程
1、3及び17で使用されるようなハロゲン化炭化水素
類、ニトロベンゼンなどが挙げられる。触媒としては、
例えば塩化アルミニウム、塩化鉛、塩化第1鉄、塩化第
2鉄、四塩化チタン、塩化スズ、塩化亜鉛、ポリリン酸
などのルイス酸が挙げられる。The reaction in the reaction step 8 is a usual Friedel-Crafts reaction, which is carried out in the presence of a solvent and a catalyst.
To + 100 ° C., and the reaction time is 0.1 to 100 hours. Examples of the solvent include carbon disulfide, halogenated hydrocarbons used in the above reaction steps 1, 3, and 17, and nitrobenzene. As a catalyst,
For example, Lewis acids such as aluminum chloride, lead chloride, ferrous chloride, ferric chloride, titanium tetrachloride, tin chloride, zinc chloride, polyphosphoric acid and the like can be mentioned.
【0051】前記反応工程9及び10の反応は、通常の
グリニャール反応であり、溶媒の存在下で行なわれ、反
応温度は−20〜+200℃、望ましくは−10〜+1
00℃であり、反応時間は0.1〜100時間である。
溶媒としては、前記反応工程1、3及び17で使用され
るようなエーテル類が挙げられる。The reaction in the above reaction steps 9 and 10 is a usual Grignard reaction, which is carried out in the presence of a solvent at a reaction temperature of -20 to + 200 ° C., preferably -10 to +1.
The reaction time is 0.1 to 100 hours.
Examples of the solvent include ethers used in the above-mentioned reaction steps 1, 3, and 17.
【0052】前記反応工程11及び12の第1段目の反
応は、通常のウイッティヒ反応であり、塩基、溶媒の存
在下で行われ、反応温度は−20〜+200℃、望まし
くは−10〜+150℃であり、反応時間は0.1〜1
00時間である。塩基としては、アルカリ(土類)金属
の水酸化物、炭酸塩、酢酸塩又はブチルリチウムのよう
な有機金属化合物などが挙げられる。溶媒としては、炭
化水素類、前記反応工程1、3及び17で使用されるよ
うなエーテル類、アルコール類、非プロトン性極性溶
媒、芳香族炭化水素類、ハロゲン化芳香族炭化水素類、
ハロゲン化炭化水素類及び水などが挙げられ、これら溶
媒を混合して使用してもよい。The first-stage reaction of the reaction steps 11 and 12 is a usual Wittig reaction, which is carried out in the presence of a base and a solvent, at a reaction temperature of -20 to + 200 ° C., preferably -10 to + 150 ° ° C and the reaction time is 0.1 to 1
00 hours. Examples of the base include hydroxides, carbonates, acetates, and organometallic compounds such as butyllithium of alkali (earth) metals. Examples of the solvent include hydrocarbons, ethers, alcohols, aprotic polar solvents, aromatic hydrocarbons, halogenated aromatic hydrocarbons, and the like, as used in Reaction Steps 1, 3, and 17.
Examples thereof include halogenated hydrocarbons and water, and these solvents may be used as a mixture.
【0053】前記反応工程11及び12の第2段目の反
応は、通常のハロゲン化反応であり、過酸化物の存在下
または光照射下でハロゲン(ここでのハロゲンは望まし
くは臭素または塩素である)を付加させる。反応温度は
−20〜+200℃、望ましくは−10〜+100℃で
あり、反応時間は0.1〜100時間である。溶媒は望
ましくは炭化水素類、ハロゲン化炭化水素類を用いる
が、前記反応工程1、3及び17の溶媒も使用できるThe second-stage reaction of the above reaction steps 11 and 12 is a usual halogenation reaction, which is carried out in the presence of a peroxide or under irradiation with light. Is added). The reaction temperature is -20 to + 200 ° C, preferably -10 to + 100 ° C, and the reaction time is 0.1 to 100 hours. As the solvent, preferably used are hydrocarbons and halogenated hydrocarbons, but the solvents in the above reaction steps 1, 3 and 17 can also be used.
【0054】前記反応工程11及び12の第3段目の反
応は、通常の脱ハロゲン化反応であり、溶媒の存在下に
脱ハロゲン化剤により行なう脱ハロゲン化剤としてはア
ルカリ金属及びそのアルコラート、水酸化物などが挙げ
られる。反応温度は−20〜+200℃、望ましくは−
10〜+150℃であり、反応時間は0.1〜100時
間である。溶媒は前記第1段目の反応で使用できるもの
と同様のものが使用できる。The third-stage reaction of the above reaction steps 11 and 12 is a usual dehalogenation reaction. As the dehalogenating agent carried out by a dehalogenating agent in the presence of a solvent, alkali metal and its alcoholate, Hydroxide and the like. The reaction temperature is -20 to + 200 ° C, preferably-
The reaction time is from 0.1 to 100 hours. The same solvent as that used in the first-stage reaction can be used as the solvent.
【0055】前記反応工程11及び12の第4段目の反
応は、通常の酸化反応であり、酸触媒の存在下、水銀
(II)塩等を用いて酸化する。反応温度は−20〜+
200℃、望ましくは−10〜+150℃であり、反応
時間は0.1〜100時間である。溶媒は酢酸、前記第
1段目の反応で使用できるものと同様のものが使用で
き、これら溶媒を混合して使用してもよい。酸触媒とし
ては硫酸、硝酸などの無機酸、酢酸、トリフルオロ酢酸
などの有機酸などが用いられる。前記反応工程13の反
応は、通常の酸化反応であり、溶媒及び酸化剤の存在下
に行なわれる。反応温度は−20〜+200℃、望まし
くは−10〜+150℃であり、反応時間は0.1〜1
00時間である。酸化剤としてはクロム(VI)塩、四
酢酸鉛、硝酸、ジメチルスルホキシドなどが挙げられ
る。溶媒としては、水、酢酸が主に使用され、炭化水素
類、ハロゲン化芳香族炭化水素類、前記反応工程1、3
及び17で使用されるような非プロトン性極性溶媒、芳
香族炭化水素類、ハロゲン化炭化水素類が挙げられ、こ
れら溶媒を混合して使用してもよい。The fourth stage reaction in the above reaction steps 11 and 12 is a normal oxidation reaction, which is oxidized using a mercury (II) salt or the like in the presence of an acid catalyst. Reaction temperature is -20 to +
The temperature is 200C, preferably -10 to + 150C, and the reaction time is 0.1 to 100 hours. As the solvent, acetic acid and the same solvents as those used in the first-stage reaction can be used, and these solvents may be mixed and used. Examples of the acid catalyst include inorganic acids such as sulfuric acid and nitric acid, and organic acids such as acetic acid and trifluoroacetic acid. The reaction in the reaction step 13 is a normal oxidation reaction, and is performed in the presence of a solvent and an oxidizing agent. The reaction temperature is -20 to + 200 ° C, preferably -10 to + 150 ° C, and the reaction time is 0.1 to 1
00 hours. Examples of the oxidizing agent include chromium (VI) salt, lead tetraacetate, nitric acid, dimethyl sulfoxide and the like. As the solvent, water and acetic acid are mainly used, and hydrocarbons, halogenated aromatic hydrocarbons, and the above reaction steps 1, 3
And aprotic polar solvents, aromatic hydrocarbons, and halogenated hydrocarbons such as those used in (1) and (2), and these solvents may be used as a mixture.
【0056】前記反応工程16の反応は、H2O2など
による通常の酸化反応であり、通常、溶媒の存在下で行
われ、反応温度は−20〜+200℃、望ましくは−1
0〜+100℃であり、反応時間は0.1〜100時間
である。溶媒としては、前記反応工程13の反応で使用
できるものと同様のものが使用でき、これらの溶媒を混
合して使用してもよい。The reaction in the reaction step 16 is a usual oxidation reaction using H 2 O 2 or the like, and is usually carried out in the presence of a solvent.
0 to + 100 ° C, and the reaction time is 0.1 to 100 hours. As the solvent, those similar to the ones which can be used in the reaction in the reaction step 13 can be used, and these solvents may be mixed and used.
【0057】前記反応工程18及び19の反応は必要に
より溶媒の存在下で行なわれ、反応温度は、通常0〜2
50℃、望ましくは10〜180℃であり、反応時間は
0.1〜100時間である。溶媒としては例えば前記反
応工程1、3及び17で使用されるような芳香族炭化水
素類、ハロゲン化炭化水素類、脂肪族炭化水素類、脂環
式炭化水素類などが挙げられ、これらの溶媒を混合して
使用してもよい。前記一般式(I)で表わされる化合物
の具体的合成例を記載する。The reactions in the above reaction steps 18 and 19 are carried out in the presence of a solvent if necessary.
The temperature is 50 ° C, preferably 10 to 180 ° C, and the reaction time is 0.1 to 100 hours. Examples of the solvent include aromatic hydrocarbons, halogenated hydrocarbons, aliphatic hydrocarbons, alicyclic hydrocarbons and the like as used in the above reaction steps 1, 3 and 17. May be used in combination. Specific synthesis examples of the compound represented by the general formula (I) will be described.
【0058】合成例1 〔4’−クロロ−2−(4−クロロフェニル)アセトフ
ェノン〕N’−〔1−(ジメチルアミノ)エチリデン〕
ヒドラゾン(化合物No.1)の合成 (1)4’−クロロ−2−(4−クロロフェニル)アセ
トフェノン1.33g(5mmol)をエタノール25
mlに溶解し、そこにヒドラジン1水和物1.25g
(25mmol)を加え、これらを2時間加熱還流し
た。反応終了後、エタノールを減圧で留去し、残渣に水
を加え、ジクロロメタンで抽出した。無水硫酸ナトリウ
ムで乾燥し、溶媒を留去すると、1.44gの〔4’−
クロロ−2−(4−クロロフェニル)アセトフェノン〕
ヒドラゾンが黄色油状物として得られた。 (2)前記工程(1)で得られた〔4’−クロロ−2−
(4−クロロフェニル)アセトフェノン〕ヒドラゾン
1.0g(3.6mmol)にN,N−ジメチルアセト
アミドジメチルアセタール0.51g(4.2mmo
l)を加え、120℃で2時間加熱した。反応終了後、
反応液をシリカゲルカラムクロマトグラフィー(展開溶
媒=酢酸エチル:n−ヘキサン=1:4)で精製して、
融点125〜127℃の目的物(化合物No.1)0.
56gを得た。Synthesis Example 1 [4'-chloro-2- (4-chlorophenyl) acetophenone] N '-[1- (dimethylamino) ethylidene]
Synthesis of Hydrazone (Compound No. 1) (1) 1.33 g (5 mmol) of 4′-chloro-2- (4-chlorophenyl) acetophenone was added to ethanol 25
hydrazine monohydrate (1.25 g)
(25 mmol) were added and these were heated to reflux for 2 hours. After completion of the reaction, ethanol was distilled off under reduced pressure, water was added to the residue, and the mixture was extracted with dichloromethane. After drying over anhydrous sodium sulfate and evaporating the solvent, 1.44 g of [4′-
Chloro-2- (4-chlorophenyl) acetophenone]
The hydrazone was obtained as a yellow oil. (2) [4′-chloro-2- obtained in the above step (1)
(4-Chlorophenyl) acetophenone] hydrazone (1.0 g, 3.6 mmol) and N, N-dimethylacetamide dimethyl acetal (0.51 g, 4.2 mmol)
1) and heated at 120 ° C. for 2 hours. After the reaction,
The reaction solution was purified by silica gel column chromatography (developing solvent = ethyl acetate: n-hexane = 1: 4).
The target compound having a melting point of 125 to 127 ° C (Compound No. 1)
56 g were obtained.
【0059】合成例2 メチル3−〔1,2−ビス(4−クロロフェニル)エチ
リデン〕カーバゼート(化合物No.201)の合成 前記合成例1(1)で得られた〔4’−クロロ−2−
(4−クロロフェニル)アセトフェノン〕ヒドラゾン
0.43g(1.5mmol)を5mlのピリジンに溶
解し、そこへ氷冷しながら0.2ml(2.5mmo
l)のクロロ炭酸メチルを滴下し、滴下終了後、室温で
3時間攪拌した。反応終了後、混合物を水中に投入しジ
クロロメタンで抽出し、無水硫酸ナトリウムで乾燥した
後減圧濃縮した。残渣をシリカゲルカラムクロマトグラ
フィー(展開溶媒=酢酸エチル:n−ヘキサン=3:
7)で精製して、融点156〜159℃の目的物(化合
物No.201)0.37gを得た。Synthesis Example 2 Synthesis of Methyl 3- [1,2-bis (4-chlorophenyl) ethylidene] carbazate (Compound No. 201) [4′-chloro-2-
(4-Chlorophenyl) acetophenone] hydrazone (0.43 g, 1.5 mmol) was dissolved in 5 ml of pyridine, and 0.2 ml (2.5 mmol) was added thereto while cooling with ice.
1) Methyl chlorocarbonate was added dropwise, and after completion of the addition, the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the mixture was poured into water, extracted with dichloromethane, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (developing solvent = ethyl acetate: n-hexane = 3:
7) to obtain 0.37 g of the target compound (compound No. 201) having a melting point of 156 to 159 ° C.
【0060】合成例3 〔4’−クロロ−2−(4−クロロフェニル)アセトフ
ェノン〕−4−(4−トリフルオロメチルフェニル)セ
ミカルバゾン(化合物No.200)の合成 p−アミノベンゾトリフルオリド0.97g(6mmo
l)を10mlの酢酸エチルに溶解し、そこへ1.1m
l(9mmol)のトリクロロメチルクロロフォルメー
トを加えて、2時間加熱還流した後、過剰のトリクロロ
メチルクロロフォルメート及び酢酸エチルを減圧で留去
した。残渣を5mlのエーテルに溶解し、前記合成例1
(1)と同様にして得られた〔4’−クロロ−2−(4
−クロロフェニル)アセトフェノン〕ヒドラゾン1.4
g(5mmol)のジエチルエーテル20ml溶液中に
氷冷下で滴下した。滴下終了後室温で1.5時間攪拌し
た。反応終了後、溶媒を留去し、少量の水を加えてジク
ロロメタンで抽出し、無水硫酸ナトリウムで乾燥後減圧
濃縮した。残渣をシリカゲルカラムクロマトグラフィー
(展開溶媒=酢酸エチル:n−ヘキサン=1:4)で精
製して、融点194〜198℃の目的物(化合物No.
200)1.53gを得た。Synthesis Example 3 Synthesis of [4'-chloro-2- (4-chlorophenyl) acetophenone] -4- (4-trifluoromethylphenyl) semicarbazone (Compound No. 200) 0.97 g of p-aminobenzotrifluoride (6mmo
l) was dissolved in 10 ml of ethyl acetate, and 1.1 m
After adding 1 (9 mmol) of trichloromethyl chloroformate and heating under reflux for 2 hours, excess trichloromethyl chloroformate and ethyl acetate were distilled off under reduced pressure. The residue was dissolved in 5 ml of ether.
[4′-chloro-2- (4
-Chlorophenyl) acetophenone] hydrazone 1.4
g (5 mmol) in 20 ml of diethyl ether was added dropwise under ice-cooling. After completion of the dropwise addition, the mixture was stirred at room temperature for 1.5 hours. After completion of the reaction, the solvent was distilled off, a small amount of water was added, the mixture was extracted with dichloromethane, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent = ethyl acetate: n-hexane = 1: 4) to give the desired product having a melting point of 194 to 198 ° C. (Compound No.
200) 1.53 g were obtained.
【0061】合成例4 〔4’−クロロ−2−(4−ターシャリーブチルフェニ
ル)アセトフェノン〕N’−〔1−(ジメチルアミノ)
エチリデン〕ヒドラゾン(化合物No.32)の合成 (1)マグネシウム(削状)0.7g及びヨウ素の小片
100mgを無水ジエチルエーテル5mlに加えた後、
窒素気流下にp−ブロモクロロベンゼン5.6gの無水
ジエチルエーテル10ml溶液をゆるやかに還流するの
に十分な速度で滴下した。この溶液を室温で20分間攪
拌して反応させた後、無水ジエチルエーテル5ml溶液
にp−ターシャリーブチルフェニルアセトニトリル4.
8gを溶解した溶液を、ゆるやかに還流するのに十分な
速度で滴下した。この溶液をさらに30分間攪拌して反
応させた。反応終了後、氷10gと6N−塩酸130m
lとの混合液を加え、酢酸エチルで抽出した。この抽出
層を水及び飽和食塩水で洗浄後、無水硫酸ナトリウムで
乾燥し、次いで減圧下で濃縮した。残渣をシリカゲルカ
ラムクロマトグラフィー(展開溶媒=酢酸エチル:n−
ヘキサン=1:9)で精製して、4’−クロロ−2−
(4−ターシャリーブチルフェニル)アセトフェノン
1.3gを得た。 (2)4’−クロロ−2−(4−ターシャリーブチルフ
ェニル)アセトフェノン1.3g(4.5mmol)を
エタノール15mlに溶解し、そこにヒドラジン1水和
物0.2g(4.5mmol)を加えこれらを3時間加
熱還流した。反応終了後、エタノールを減圧下で留去
し、残渣に水を加え、ジクロロメタンで抽出した。無水
硫酸ナトリウムで乾燥し、溶媒を留去すると1.3gの
〔4’−クロロ−2−(4−ターシャリーブチルフェニ
ル)アセトフェノン〕ヒドラゾンを黄色油状物として得
た。 (3)前記工程(2)で得られた〔4’−クロロ−2−
(4−ターシャリーブチルフェニル)アセトフェノン〕
ヒドラゾン1.3g(4.3mmol)をアセトニトリ
ル15mlに溶解し、そこにN,N−ジメチルアセトア
ミドジメチルアセタール0.6g(4.7mmol)を
加え24時間加熱還流した。反応終了後、アセトニトリ
ルを減圧下で留去し残渣をシリカゲルカラムクロマトグ
ラフィー(展開溶媒=酢酸エチル:n−ヘキサン=1:
8)で精製して、融点100〜101℃の目的物(化合
物No.32)0.4gを得た。Synthesis Example 4 [4'-chloro-2- (4-tert-butylphenyl) acetophenone] N '-[1- (dimethylamino)
Synthesis of [ethylidene] hydrazone (compound No. 32) (1) After adding 0.7 g of magnesium (milled) and 100 mg of small pieces of iodine to 5 ml of anhydrous diethyl ether,
Under a nitrogen stream, a solution of 5.6 g of p-bromochlorobenzene in 10 ml of anhydrous diethyl ether was added dropwise at a rate sufficient to cause gentle reflux. This solution was stirred at room temperature for 20 minutes to react, and then p-tert-butylphenylacetonitrile was added to a solution of 5 ml of anhydrous diethyl ether.
The solution in which 8 g was dissolved was added dropwise at a rate sufficient to slowly reflux. The solution was stirred for an additional 30 minutes to react. After completion of the reaction, 10 g of ice and 130 m of 6N hydrochloric acid were used.
The mixture was added with l and extracted with ethyl acetate. The extract was washed with water and saturated saline, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (developing solvent = ethyl acetate: n-
Hexane = 1: 9) to give 4'-chloro-2-
1.3 g of (4-tert-butylphenyl) acetophenone was obtained. (2) 1.3 g (4.5 mmol) of 4'-chloro-2- (4-tert-butylphenyl) acetophenone was dissolved in 15 ml of ethanol, and 0.2 g (4.5 mmol) of hydrazine monohydrate was added thereto. In addition, these were heated under reflux for 3 hours. After completion of the reaction, ethanol was distilled off under reduced pressure, water was added to the residue, and the mixture was extracted with dichloromethane. After drying over anhydrous sodium sulfate and evaporating the solvent, 1.3 g of [4'-chloro-2- (4-tert-butylphenyl) acetophenone] hydrazone was obtained as a yellow oil. (3) [4′-chloro-2- obtained in the above step (2)
(4-tert-butylphenyl) acetophenone]
1.3 g (4.3 mmol) of hydrazone was dissolved in 15 ml of acetonitrile, and 0.6 g (4.7 mmol) of N, N-dimethylacetamide dimethyl acetal was added thereto, followed by heating under reflux for 24 hours. After completion of the reaction, acetonitrile was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (developing solvent = ethyl acetate: n-hexane = 1: 1).
Purification by 8) gave 0.4 g of the desired product (compound No. 32) having a melting point of 100 to 101 ° C.
【0062】合成例5 〔4’−フルオロ−2−(4−トリフルオロメチルフェ
ニル)アセトフェノン〕N’−〔1−(ジメチルアミ
ノ)エチリデン〕ヒドラゾン(化合物No.38)の合
成 (1)4−フルオロベンズアルデヒド8.9g(72m
mol)、(4−トリフルオロメチルベンジル)トリフ
ェニルホスホニウムクロライド32g(72mmol)
を塩化メチレン300mlに溶解し激しく攪拌しなが
ら、室温で3N水酸化ナトリウム280ml(0.84
mol)を滴下した。滴下終了後室温で2時間攪拌し
た。反応終了後、分液し、有機層を2回水洗した。無水
硫酸ナトリウムで乾燥し、溶媒を留去した。残渣をシリ
カゲルカラムクロマトグラフィー(展開溶媒:n−ヘキ
サン)で精製して、4−フルオロ−4’−トリフルオロ
メチルスチルベン12.4gを得た。 (2)クロロホルム80mlに4−フルオロ−4’−ト
リフルオロメチルスチルベン12.4g(47mmo
l)を溶解した溶液を、160wの水銀灯光を照射しな
がら40℃で臭素2.4ml(47mmol)の20m
lのクロロホルム溶液を滴下し、30分間攪拌を続け
た。反応終了後、溶媒を留去し黄色の油状物を得た。精
製せずにこのものをエタノール100mlに溶解し、加
熱還流しながら水45mlに水酸化カリウム12.3g
を溶解した水溶液を滴下した。滴下終了後、3時間加熱
還流を続けた。反応終了後エタノールを留去し、残渣に
水を加えてエーテルで抽出した。無水硫酸ナトリウムで
乾燥し、溶媒を留去し4−フルオロ−4’−トリフルオ
ロメチルトラン12.2gを黄色固体として得た。この
ものは精製せずに次の反応に用いた。 (3)4−フルオロ−4’−トリフルオロメチルトラン
12.2g(46mmol)に水60ml、酢酸60m
l、硫酸40ml、硫酸第2水銀13.6g(46mm
ol)を加えて90℃で3.5時間加熱攪拌した。反応
終了後水を加えてエーテルで抽出し、無水硫酸ナトリウ
ムで乾燥し、溶媒を留去し残渣をシリカゲルカラムクロ
マトグラフィー(展開溶媒=酢酸エチル:n−ヘキサン
=1:10)で精製して、融点87〜89℃の4’−フ
ルオロ−2−(4−トリフルオロメチルフェニル)アセ
トフェノン5.1gを得た。 (4)4’−フルオロ−2−(4−トリフルオロメチル
フェニル)アセトフェノン5.1g(18.1mmo
l)をエタノール100mlに溶解し、そこにヒドラジ
ン1水和物8.8ml(181mmol)を加えこれら
を2時間加熱還流した。反応終了後エタノールを減圧下
で留去し、残渣に水を加え、ジクロロメタンで抽出し
た。無水硫酸ナトリウムで乾燥し、溶媒を留去すると
〔4’−フルオロ−2−(4−トリフルオロメチルフェ
ニル)アセトフェノン〕ヒドラゾンが黄色油状物として
得られた。 (5)前記工程(4)で得られた〔4’−フルオロ−2
−(4−トリフルオロメチルフェニル)アセトフェノ
ン〕ヒドラゾンにN,N−ジメチルアセトアミドジメチ
ルアセタール3.13g(23.5mmol)を加え1
20℃で2時間加熱した。反応終了後、残渣をシリカゲ
ルカラムクロマトグラフィー(展開溶媒=酢酸エチル:
n−ヘキサン=1:19)で精製して、融点86〜88
℃の目的物(化合物No.38)3.10gを得た。Synthesis Example 5 Synthesis of [4′-fluoro-2- (4-trifluoromethylphenyl) acetophenone] N ′-[1- (dimethylamino) ethylidene] hydrazone (Compound No. 38) (1) 4- 8.9 g of fluorobenzaldehyde (72 m
mol), (4-trifluoromethylbenzyl) triphenylphosphonium chloride 32 g (72 mmol)
Is dissolved in 300 ml of methylene chloride, and while stirring vigorously, 280 ml of 3N sodium hydroxide (0.84
mol) was added dropwise. After completion of the dropwise addition, the mixture was stirred at room temperature for 2 hours. After the completion of the reaction, liquid separation was performed, and the organic layer was washed twice with water. After drying over anhydrous sodium sulfate, the solvent was distilled off. The residue was purified by silica gel column chromatography (developing solvent: n-hexane) to obtain 12.4 g of 4-fluoro-4′-trifluoromethylstilbene. (2) 12.4 g (47 mmol) of 4-fluoro-4'-trifluoromethylstilbene was added to 80 ml of chloroform.
l) was dissolved in a solution of 2.4 ml (47 mmol) of bromine in 20 m at 40 ° C while irradiating with a 160 w mercury lamp.
of chloroform solution was added dropwise, and stirring was continued for 30 minutes. After completion of the reaction, the solvent was distilled off to obtain a yellow oily substance. This was dissolved in 100 ml of ethanol without purification, and 12.3 g of potassium hydroxide was added to 45 ml of water while heating under reflux.
An aqueous solution in which was dissolved was added dropwise. After the completion of the dropwise addition, heating and reflux were continued for 3 hours. After completion of the reaction, ethanol was distilled off, water was added to the residue, and the mixture was extracted with ether. After drying over anhydrous sodium sulfate, the solvent was distilled off to obtain 12.2 g of 4-fluoro-4'-trifluoromethyltran as a yellow solid. This was used for the next reaction without purification. (3) Water (60 ml) and acetic acid (60 m) were added to 12.2 g (46 mmol) of 4-fluoro-4′-trifluoromethyltran.
1, 40 ml of sulfuric acid, 13.6 g of mercuric sulfate (46 mm
ol) and heated and stirred at 90 ° C. for 3.5 hours. After completion of the reaction, water was added, the mixture was extracted with ether, dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was purified by silica gel column chromatography (developing solvent = ethyl acetate: n-hexane = 1: 10). 5.1 g of 4′-fluoro-2- (4-trifluoromethylphenyl) acetophenone having a melting point of 87 to 89 ° C. was obtained. (4) 5.1 g of 4'-fluoro-2- (4-trifluoromethylphenyl) acetophenone (18.1 mmol)
l) was dissolved in 100 ml of ethanol, 8.8 ml (181 mmol) of hydrazine monohydrate was added thereto, and these were heated under reflux for 2 hours. After completion of the reaction, ethanol was distilled off under reduced pressure, water was added to the residue, and the mixture was extracted with dichloromethane. After drying over anhydrous sodium sulfate and evaporating the solvent, [4'-fluoro-2- (4-trifluoromethylphenyl) acetophenone] hydrazone was obtained as a yellow oil. (5) [4′-fluoro-2 obtained in the above step (4)
-(4-Trifluoromethylphenyl) acetophenone] hydrazone, and 3.13 g (23.5 mmol) of N, N-dimethylacetamidodimethylacetal were added.
Heated at 20 ° C. for 2 hours. After completion of the reaction, the residue was subjected to silica gel column chromatography (developing solvent = ethyl acetate:
n-hexane = 1: 19) to give a melting point of 86-88.
3.10 g of the target product (compound No. 38) at ℃ was obtained.
【0063】合成例6 〔4’−クロロ−2−(4−トリフルオロメチルフェニ
ル)アセトフエノン〕N’−〔1−(ジメチルアミノ)
エチリデン〕ヒドラゾン(化合物No.9)合成 前記合成例5(1)の4−フルオロベンズアルデヒドを
4−クロロベンズアルデヒドに代える以外は前記合成例
5の場合とほぼ同様にして行い、融点94〜97℃の目
的物(化合物No.9)を得た。Synthesis Example 6 [4'-chloro-2- (4-trifluoromethylphenyl) acetophenone] N '-[1- (dimethylamino)
[Ethylidene] hydrazone (Compound No. 9) Synthesis The synthesis was conducted in substantially the same manner as in Synthesis Example 5 except that 4-fluorobenzaldehyde in Synthesis Example 5 (1) was replaced with 4-chlorobenzaldehyde. The desired product (Compound No. 9) was obtained.
【0064】合成例7 4’−フルオロ−2−(4−ターシャリーブチルフェニ
ル)アセトフェノンN’−〔1−(ジメチルアミノ)エ
チリデン〕ヒドラゾンの合成(化合物No.60) (1)4’−フルオロ−2−(4−ターシャリーブチル
フェニル)アセトフェノン3g(11mmol)、アセ
チルヒドラジド0.8g(11mmol)、酢酸60m
g(1mmol)及びエタノール20mlの混合物を2
0時間加熱還流した。反応終了後エタノールを減圧下に
留去して反応物を濃縮した後、シリカゲルカラムクロマ
トグラフィー(展開溶媒=n−ヘキサン:酢酸エチル=
4:1)で精製して、融点132〜134℃の4’−フ
ルオロ−2−(4−ターシャリーブチルフェニル)アセ
トフェノンN’−アセチルヒドラゾン1.09gを得
た。 (2)4’−フルオロ−2−(4−ターシャリーブチル
フェニル)アセトフェノンN’−アセチルヒドラゾン1
g(3.1mmol)、五塩化リン0.64g(3.1
mmol)及びジクロロメタン15mlの混合溶液を室
温下で1時間攪拌した後加熱還流下で2時間反応した。
反応終了後、反応溶液を減圧下に濃縮した後、新たにジ
クロロメタン10mlを加え、更にジメチルアミン1.
38g(15mmol)を室温下で1度に加え、同温度
で2時間攪拌して反応させた。反応終了後、ジクロロメ
タン30mlで希釈し、水で洗浄後無水硫酸ナトリウム
で乾燥した。溶媒を減圧下で濃縮した後シリカゲルカラ
ムクロマトグラフィー(展開溶媒=n−ヘキサン:酢酸
エチル=9:1)で精製して、融点65〜67℃の目的
物(化合物No.60)0.33gを得た。 次に前記一般式(I)で表わされる化合物の代表例を表
1〜表23に記載する。Synthesis Example 7 Synthesis of 4'-fluoro-2- (4-tert-butylphenyl) acetophenone N '-[1- (dimethylamino) ethylidene] hydrazone (Compound No. 60) (1) 4'-Fluoro -2- (4-tert-butylphenyl) acetophenone 3 g (11 mmol), acetylhydrazide 0.8 g (11 mmol), acetic acid 60 m
g (1 mmol) and ethanol 20 ml
The mixture was refluxed for 0 hours. After completion of the reaction, ethanol was distilled off under reduced pressure to concentrate the reaction product, and then silica gel column chromatography (developing solvent = n-hexane: ethyl acetate =
Purification by 4: 1) gave 1.09 g of 4'-fluoro-2- (4-tert-butylphenyl) acetophenone N'-acetylhydrazone having a melting point of 132 to 134 ° C. (2) 4'-fluoro-2- (4-tert-butylphenyl) acetophenone N'-acetylhydrazone 1
g (3.1 mmol), phosphorus pentachloride 0.64 g (3.1
(mmol) and 15 ml of dichloromethane were stirred at room temperature for 1 hour and then reacted under heating and reflux for 2 hours.
After completion of the reaction, the reaction solution was concentrated under reduced pressure, and 10 ml of dichloromethane was newly added.
38 g (15 mmol) was added at once at room temperature, and the mixture was stirred and reacted at the same temperature for 2 hours. After the completion of the reaction, the reaction mixture was diluted with 30 ml of dichloromethane, washed with water and dried over anhydrous sodium sulfate. After concentrating the solvent under reduced pressure, the residue was purified by silica gel column chromatography (developing solvent = n-hexane: ethyl acetate = 9: 1) to obtain 0.33 g of the desired product (compound No. 60) having a melting point of 65 to 67 ° C. Obtained. Next, typical examples of the compound represented by the general formula (I) are described in Tables 1 to 23.
【0065】[0065]
【表1】 [Table 1]
【0066】[0066]
【表2】 [Table 2]
【0067】[0067]
【表3】 [Table 3]
【0068】[0068]
【表4】 [Table 4]
【0069】[0069]
【表5】 [Table 5]
【0070】[0070]
【表6】 [Table 6]
【0071】[0071]
【表7】 [Table 7]
【0072】[0072]
【表8】 [Table 8]
【0073】[0073]
【表9】 [Table 9]
【0074】[0074]
【表10】 [Table 10]
【0075】[0075]
【表11】 [Table 11]
【0076】[0076]
【表12】 [Table 12]
【0077】[0077]
【表13】 [Table 13]
【0078】[0078]
【表14】 [Table 14]
【0079】[0079]
【表15】 [Table 15]
【0080】[0080]
【表16】 [Table 16]
【0081】[0081]
【表17】 [Table 17]
【0082】[0082]
【表18】 [Table 18]
【0083】[0083]
【表19】 [Table 19]
【0084】[0084]
【表20】 [Table 20]
【0085】[0085]
【表21】 [Table 21]
【0086】[0086]
【表22】 [Table 22]
【0087】[0087]
【表23】 [Table 23]
【0088】更に前記一般式(IX)で表わされる化合
物であって、前記一般式(I)で表わされる化合物の範
囲外のものの代表例を表24〜表26に記載する。Further, Tables 24 to 26 show typical examples of the compounds represented by the general formula (IX), which are outside the range of the compounds represented by the general formula (I).
【0089】[0089]
【表24】 [Table 24]
【0090】[0090]
【表25】 [Table 25]
【0091】[0091]
【表26】 [Table 26]
【0092】前記一般式(II−5)で表わされる化合
物は、前記一般式(I)及び(IX)で表わされる化合
物の中間体であって、新規化合物であると思われる。こ
れらの化合物の代表例を表27〜表31に記載する。The compound represented by formula (II-5) is an intermediate of the compounds represented by formulas (I) and (IX), and is considered to be a novel compound. Representative examples of these compounds are shown in Tables 27 to 31.
【0093】[0093]
【表27】 [Table 27]
【0094】[0094]
【表28】 [Table 28]
【0095】[0095]
【表29】 [Table 29]
【0096】[0096]
【表30】 [Table 30]
【0097】[0097]
【表31】 [Table 31]
【0098】表1〜表31中、Phはフェニル基を、t
−Bu、n−Bu又はs−Buはターシャリー、ノルマ
ル又はセカンダリーの各ブチル基を、iso−Pr又は
n−Prはイソ又はノルマルの各プロピル基を、cyc
lo−Pr又はcyclo−Hexはシクロプロピル基
又はシクロヘキシル基をそれぞれ表わす。また各置換基
の数字は置換基の位置を示し例えば化合物No.1にお
けるR1の4−Clはベンゼン環の4位にClが位置す
ることを表わす。化合物No.221は化合物No.2
15の異性体である。In Tables 1 to 31, Ph represents a phenyl group and t represents
-Bu, n-Bu or s-Bu is a tertiary, normal or secondary butyl group, iso-Pr or n-Pr is an iso or normal propyl group, cyc
lo-Pr or cyclo-Hex represents a cyclopropyl group or a cyclohexyl group, respectively. The number of each substituent indicates the position of the substituent, for example, Compound No. 4-Cl of R 1 in 1 represents that Cl is located at the 4-position of the benzene ring. Compound No. 221 is Compound No. 2
15 isomers.
【0099】前記一般式(I)及び(IX)で表わされ
る化合物は有害生物防除剤の有効成分として優れた活性
を示す。例えば、ナミハダニ、ニセナミハダニ、ミカン
ハダニ、ネダニなどのような植物寄生性ダニ類、コナ
ガ、ヨトウムシ、ハスモンヨトウ、コドリンガ、ボール
ワーム、タバコバットワーム、マイマイガ、コラノメイ
ガ、チヤノコカクモンハマキ、コロラドハムシ、ウリハ
ムシ、ボールウィービル、アブラムシ類、ウンカ類、ヨ
コバイ類、カイガラムシ類、カメムシ類、コナジラミ
類、アザミウマ類、バッタ類、ハナバエ類、コガネムシ
類、タマナヤガ、カプラヤガ、アリ類などのような農業
害虫類、イエダニ、ゴキブリ類、イエバエ、アカイエカ
のような衛生害虫類、バクガ、アズキゾウムシ、コクヌ
ストモドキ、ゴミムシダマシ類などのような貯殻害虫
類、イガ、ヒメカツオブシムシ、シロアリ類などのよう
な衣類、家屋害虫類、その他家畜などに寄生するノミ
類、シラミ類、ハエ類などに対しても有効であり、更に
はネコブセンチュウ類、シストセンチュウ類、ネグサレ
センチュウ類、イネシンガレセンチュウ、イチゴメセン
チュウ、マツノザイセンチュウなどのような植物寄生性
線虫類に対しても有効である。また、土壌害虫類に対し
ても有効である。ここに言う土壌害虫としては、ナメク
ジ、マイマイのような腹足類、ダンゴムシ、ワラジムシ
などのような等脚類などがあげられる。The compounds represented by the general formulas (I) and (IX) exhibit excellent activity as an active ingredient of a pesticide. For example, plant parasitic mites such as spider mites, spider mites, mandarin spider mites, spider mites, mites, mothweeds, armyworms, tossinnia, codling moths, ball worms, tobacco bat worms, gypsy moths, kora nomeiga, cyano sylvestris, colorado beetles, turtle beetles, Agricultural pests such as ball-weevil, aphids, planthoppers, leafhoppers, scale insects, stink bugs, whiteflies, thrips, grasshoppers, flower flies, scarab beetles, tamanayaga, caprayaga, ants, etc., house dust mites, Sanitary pests such as cockroaches, house flies, and house mosquitoes, storage pests such as stag beetles, azuki beetles, kokusutomodoki, and beetles, clothing and house pests such as moths, bark beetles, termites, and others. livestock It is also effective against fleas, lice, flies, etc., which are parasitic on throats. It is also effective against various plant parasitic nematodes. It is also effective against soil pests. Examples of the soil pests mentioned here include gastropods such as slugs and snails, and isopods such as duck beetles and scabies.
【0100】上記のような各種有害生物のなかでも、特
に鱗翅目害虫及び鞘翅目害虫に対してすぐれた活性を示
す。また有機リン剤抵抗性やピレスロイド剤抵抗性のコ
ナガ、イエバエなどの害虫に対しても有効である。さら
に浸透移行性を有していることから、本発明でいう化合
物を土壌に処理などをすることによって土壌有害昆虫
類、ダニ類、線虫類、腹足類、等脚類の防除と同時に茎
葉部の害虫類をも防除することができる。また、哺乳動
物、魚類さらに益虫などに対して高い安全性を有し、有
害生物防除剤として良好な性質を有する。Among the various pests described above, they exhibit excellent activity against lepidopteran and coleopteran pests. It is also effective against pests such as oak and housefly which are resistant to organophosphates and pyrethroids. In addition, because it has osmotic transfer, by treating the soil with the compound of the present invention, soil harmful insects, mites, nematodes, gastropods, and at the same time as controlling the foliage of the isopoda. Pests can also be controlled. In addition, it has high safety against mammals, fish and beneficial insects, and has good properties as a pesticide.
【0101】本発明でいう化合物を有害生物防除剤の有
効成分として使用するに際しては、従来の農薬の製剤の
場合と同様に農薬補助剤と共に乳剤、粉剤、粒剤、水和
剤、顆粒水和剤、懸濁剤、液剤、エアゾール剤、ペース
ト剤などの種々の形態に製剤することができる。これら
の配合割合は通常有効成分0.1〜90重量部望ましく
は0.5〜90重量部、さらに望ましくは0.5〜80
重量部に対し、農薬補助剤10〜99.9重量部、望ま
しくは10〜99.5重量部、さらに望ましくは20〜
99.5重量部である。これらの製剤の実際の使用に際
しては、そのまま使用するか、または水等の希釈剤で所
定濃度に希釈して使用することができる。When the compound of the present invention is used as an active ingredient of a pesticidal agent, emulsions, powders, granules, wettable powders, granule hydration agents are used together with pesticidal auxiliaries as in the case of conventional pesticide preparations. It can be formulated in various forms such as agents, suspensions, solutions, aerosols, pastes and the like. The mixing ratio of these components is usually 0.1 to 90 parts by weight, preferably 0.5 to 90 parts by weight, more preferably 0.5 to 80 parts by weight.
10 to 99.9 parts by weight, preferably 10 to 99.5 parts by weight, more preferably 20 to 9 parts by weight of the pesticide adjuvant with respect to parts by weight.
99.5 parts by weight. In the actual use of these preparations, they can be used as they are or diluted to a predetermined concentration with a diluent such as water.
【0102】ここにいう農薬補助剤としては、担体、乳
化剤、懸濁剤、分散剤、展着剤、浸透剤、湿潤剤、増粘
剤、消泡剤、安定剤、凍結防止剤などが挙げられ、必要
により適宜添加すればよい。担体としては、固体担体と
液体担体に分けられ、固体担体としては、澱粉、活性
炭、大豆粉、小麦粉、木粉、魚粉、粉乳などの動植物性
粉末、タルク、カオリン、ベントナイト、炭酸カルシウ
ム、ゼオライト、珪藻土、ホワイトカーボン、クレー、
アルミナなどの鉱物性粉末、硫黄粉末、無水硫酸ナトリ
ウムなどが挙げられ、液体担体としては、水、メチルア
ルコール、エチレングリコールなどのアルコール類、ア
セトン、メチルエチルケトン、N−メチル−2−ピロリ
ドンなどのケトン類、ジオキサン、テトラヒドロフラン
などのエーテル類、ケロシン、灯油などの脂肪族炭化水
素類、キシレン、トリメチルベンゼン、テトラメチルベ
ンゼン、シクロヘキサン、ソルベントナフサなどの芳香
族炭化水素類、クロロホルム、クロロベンゼンなどのハ
ロゲン化炭化水素類、ジメチルホルムアミドなどの酸ア
ミド類、酢酸エチルエステル、脂肪酸のグリセリンエス
テルなどのエステル類、アセトニトリルなどのニトリル
類、ジメチルスルホキシドなどの含硫化合物類、大豆
油、トウモロコシ油などの植物油などが挙げられる。[0102] Examples of the pesticidal auxiliary herein include a carrier, an emulsifier, a suspending agent, a dispersing agent, a spreading agent, a penetrating agent, a wetting agent, a thickening agent, an antifoaming agent, a stabilizer, and an antifreezing agent. It may be added as needed. The carrier is divided into a solid carrier and a liquid carrier, and as the solid carrier, starch, activated carbon, soybean flour, wheat flour, wood flour, fish flour, animal and plant powders such as milk powder, talc, kaolin, bentonite, calcium carbonate, zeolite, Diatomaceous earth, white carbon, clay,
Mineral powders such as alumina, sulfur powder, anhydrous sodium sulfate, etc., and liquid carriers include water, alcohols such as methyl alcohol and ethylene glycol, ketones such as acetone, methyl ethyl ketone and N-methyl-2-pyrrolidone. , Dioxane, ethers such as tetrahydrofuran, kerosene, aliphatic hydrocarbons such as kerosene, xylene, trimethylbenzene, aromatic hydrocarbons such as tetramethylbenzene, cyclohexane, solvent naphtha, halogenated hydrocarbons such as chloroform and chlorobenzene , Acid amides such as dimethylformamide, esters such as ethyl acetate and glycerin ester of fatty acid, nitriles such as acetonitrile, sulfur-containing compounds such as dimethyl sulfoxide, soybean oil, corn oil What vegetable oils and the like.
【0103】次に、本発明でいう化合物を有効成分とし
て含有する有害生物防除剤の製剤例を記載するが、有効
成分化合物及び農薬補助剤の種類、配合割合、剤型など
は記載例のみに限定されるものではない。Next, formulation examples of the pesticidal composition containing the compound of the present invention as an active ingredient will be described. The types, blending ratios, dosage forms, and the like of the active ingredient compound and the pesticide auxiliary are only described in the description examples. It is not limited.
【0104】製剤例1 (イ)化合物No.9 20重量部 (ロ)カオリン 52重量部 (ハ)リグニンスルホン酸ソーダ 8重量部 (ニ)ホワイトカーボン 20重量部 以上のものを均一に混合して水和剤とする。Formulation Example 1 (A) Compound No. 9 20 parts by weight (b) Kaolin 52 parts by weight (c) Sodium ligninsulfonate 8 parts by weight (d) White carbon 20 parts by weight The above components are uniformly mixed to obtain a wettable powder.
【0105】製剤例2 (イ)化合物No.32 5重量部 (ロ)タルク 95重量部 以上のものを均一に混合して粉剤とする。Formulation Example 2 (a) Compound No. 325 parts by weight (b) 95 parts by weight of talc The above components are uniformly mixed to form a powder.
【0106】製剤例3 (イ)化合物No.210 20重量部 (ロ)N−メチル−2−ピロリドン 10重量部 (ハ)ポリオキシエチレンアルキルフェニルエーテル 10重量部 (ニ)キシレン 60重量部 以上のものを均一に混合、溶解して乳剤とする。Formulation Example 3 (A) Compound No. 210 20 parts by weight (b) N-methyl-2-pyrrolidone 10 parts by weight (c) Polyoxyethylene alkylphenyl ether 10 parts by weight (d) xylene 60 parts by weight The above components are uniformly mixed and dissolved to form an emulsion. .
【0107】製剤例4 (イ)カオリン 83重量部 (ロ)リグニンスルホン酸ソーダ 2重量部 (ハ)ポリオキシエチレンアルキルアリールサルフェート 5重量部 (ニ)微粉シリカ 10重量部 以上の各成分の混合物と、化合物No.38とを4:1
の重量割合で混和し、水和剤とする。Formulation Example 4 (a) 83 parts by weight of kaolin (b) 2 parts by weight of sodium ligninsulfonate (c) 5 parts by weight of polyoxyethylene alkylaryl sulphate (d) 10 parts by weight of finely divided silica A mixture of the above components , Compound No. 38 and 4: 1
To obtain a wettable powder.
【0108】製剤例5 (イ)化合物No.42 40重量部 (ロ)オキシレーテッドポリアルキルフェノール フォスフェート−トリエタノールアミン 2重量部 (ハ)シリコーン 0.2重量部 (ニ)ザンサンガム 0.1重量部 (ホ)エチレングリコール 5重量部 (ヘ)水 52.7重量部 以上のものを均一に混合、粉砕して水性懸濁剤とする。Formulation Example 5 (a) Compound No. 42 40 parts by weight (b) Oxylated polyalkylphenol phosphate-triethanolamine 2 parts by weight (c) Silicone 0.2 parts by weight (d) Xanthan gum 0.1 parts by weight (e) Ethylene glycol 5 parts by weight (f) 52.7 parts by weight of water The above components are uniformly mixed and pulverized to obtain an aqueous suspension.
【0109】製剤例6 (イ)化合物No.60 75重量部 (ロ)ポリカルボン酸ナトリウム 13.5重量部 (ハ)無水硫酸ナトリウム 10重量部 (ニ)デキストリン 0.5重量部 (ホ)アルキルスルホン酸ナトリウム 1重量部 以上の各成分を高速混合細粒機に入れ、更にそこへ20
%の水を加え造粒、乾燥して顆粒水和剤が得られる。Formulation Example 6 (a) Compound No. 60 75 parts by weight (b) Sodium polycarboxylate 13.5 parts by weight (c) Anhydrous sodium sulfate 10 parts by weight (d) Dextrin 0.5 parts by weight (e) Sodium alkyl sulfonate 1 part by weight Put in the mixing granulator, and then add 20
% Water is added and granulated and dried to obtain a wettable powder.
【0110】製剤例7 (イ)化合物No.32 5重量部 (ロ)ベントナイト 33重量部 (ハ)カオリン 57重量部 (ニ)リグニンスルホン酸ソーダ 5重量部 以上の各成分に適量の造粒所要水を加え混合、造粒して
粒剤が得られる。Formulation Example 7 (a) Compound No. 325 5 parts by weight (b) Bentonite 33 parts by weight (c) Kaolin 57 parts by weight (d) Sodium ligninsulfonate 5 parts by weight Add an appropriate amount of required granulating water to each of the above components, mix and granulate to obtain granules. can get.
【0111】製剤例8 (イ)化合物No.9 2.5重量部 (ロ)N−メチル−2−ピロリドン 2.5重量部 (ハ)大豆油 95.0重量部 以上のものを均一に混合、溶解して微量散布剤(ult
ra low volume formulatio
n)とする。Formulation Example 8 (a) Compound No. 9 2.5 parts by weight (b) N-methyl-2-pyrrolidone 2.5 parts by weight (c) Soybean oil 95.0 parts by weight
ra low volume formula
n).
【0112】製剤例9 (イ)化合物No.60 5重量部 (ロ)N−メチル−2−ピロリドン 5重量部 (ハ)ポリオキシエチレンアルキルアリール(aryl) エーテル 10重量部 (ニ)キシレン 80重量部 以上のものを均一に混合し乳剤とする。Formulation Example 9 (A) Compound No. 605 5 parts by weight (b) N-methyl-2-pyrrolidone 5 parts by weight (c) polyoxyethylene alkylaryl (aryl) ether 10 parts by weight (d) xylene 80 parts by weight The above components are uniformly mixed to form an emulsion. .
【0113】製剤例10 (イ)化合物No.38 10重量部 (ロ)トウモロコシ油 77重量部 (ハ)ポリオキシエチレン硬化ヒマシ油 12重量部 (ニ)有機ベントナイト 1重量部 以上のものを均一に混合、粉砕して懸濁剤が得られる。Formulation Example 10 (a) Compound No. 38 10 parts by weight (b) Corn oil 77 parts by weight (c) Polyoxyethylene hydrogenated castor oil 12 parts by weight (d) Organic bentonite 1 part by weight The above components are uniformly mixed and pulverized to obtain a suspending agent.
【0114】また、本発明でいう化合物を有効成分とし
て含有する有害生物防除剤は、必要に応じて他の農薬、
例えば殺虫剤、殺ダニ剤、殺線虫剤、殺菌剤、抗ウイル
ス剤、誘引剤、除草剤、植物成長調整剤などと混用、併
用することができ、この場合に一層優れた効果を示すこ
ともある。例えば、殺虫剤、殺ダニ剤、或いは殺線虫剤
としては、O−(4−ブロモ−2−クロロフェニル)
O−エチル S−プロピルホスホロチオエート、O−
(2,2−ジクロロビニル) O,O−ジメチルホスフ
ェート、O−エチル O−〔3−メチル−4−(メチル
チオ)フェニル〕 N−イソプロピルホスホロアミデー
ト、O,O−ジメチル O−(4−ニトロ−m−トリ
ル)ホスホロチオエート、O−エチル O−(4−ニト
ロフェニル)フェニルホスホノチオエート、O,O−ジ
エチル O−(2−イソプロピル−6−メチルピリミジ
ン−4−イル)ホスホロチオエート、O,O−ジメチル
O−(3,5,6−トリクロロ−2−ピリジル)ホス
ホロチオエート、O,S−ジメチル N−アセチルホス
ホロアミドチオエート、O−(2,4−ジクロロフェニ
ル) O−エチル S−プロピルホスホロジチオエー
ト、(RS)−S−sec−ブチル O−エチル 2−
オキソ−1,3−チアゾリジン−3−イルホスホノチオ
エートのような有機リン酸エステル系化合物;The pesticidal composition containing the compound of the present invention as an active ingredient may contain other pesticides, if necessary.
For example, it can be mixed and used together with insecticides, acaricides, nematicides, fungicides, antiviral agents, attractants, herbicides, plant growth regulators, etc., and in this case, exhibiting even better effects There is also. For example, O- (4-bromo-2-chlorophenyl) is used as an insecticide, acaricide, or nematicide.
O-ethyl S-propyl phosphorothioate, O-
(2,2-dichlorovinyl) O, O-dimethyl phosphate, O-ethyl O- [3-methyl-4- (methylthio) phenyl] N-isopropyl phosphoramidate, O, O-dimethyl O- (4- Nitro-m-tolyl) phosphorothioate, O-ethyl O- (4-nitrophenyl) phenylphosphonothioate, O, O-diethyl O- (2-isopropyl-6-methylpyrimidin-4-yl) phosphorothioate, O, O -Dimethyl O- (3,5,6-trichloro-2-pyridyl) phosphorothioate, O, S-dimethyl N-acetyl phosphoramidothioate, O- (2,4-dichlorophenyl) O-ethyl S-propyl phosphoro Dithioate, (RS) -S-sec-butyl O-ethyl 2-
Organophosphate compounds such as oxo-1,3-thiazolidin-3-ylphosphonothioate;
【0115】1−ナフチル N−メチルカーバメート、
2−イソプロポキシフェニル N−メチルカーバメー
ト、2−メチル−2−(メチルチオ)プロピオンアルデ
ヒドO−メチルカルバモイルオキシム、2,3−ジヒド
ロ−2,2−ジメチルベンゾフラン−7−イル N−メ
チルカーバメート、ジメチル N,N’−〔チオビス
(メチルイミノ)カルボニルオキシ}〕ビスエタンイミ
ドチオエート、S−メチル N−(メチルカルバモイル
オキシ)チオアセトイミデート、N,N−ジメチル−2
−メチルカルバモイルオキシイミノ−2−(メチルチ
オ)アセトアミド、2−(エチルチオメチル)フェニル
N−メチルカーバメート、2−ジメチルアミノ−5,
6−ジメチルピリミジン−4−イル N,N−ジメチル
カーバメート、2−sec−ブチルフェニル N−メチ
ルカーバメートのようなカーバメート系化合物;S,
S’−2−ジメチルアミノトリメチレンビス(チオカー
バメート)、N,N−ジメチル−1,2,3−トリチア
ン−5−イルアミンのようなネライストキシン誘導体;
2,2,2−トリクロロ−1,1−ビス(4−クロロフ
ェニル)エタノール、4−クロロフェニル−2,4,5
−トリクロロフェニルスルホンのような有機塩素系化合
物;ビス〔トリス(2−メチル−2−フェニル−プロピ
ル)チン〕オキシドのような有機金属系化合物;1-naphthyl N-methyl carbamate,
2-isopropoxyphenyl N-methylcarbamate, 2-methyl-2- (methylthio) propionaldehyde O-methylcarbamoyloxime, 2,3-dihydro-2,2-dimethylbenzofuran-7-yl N-methylcarbamate, dimethyl N , N '-[thiobis (methylimino) carbonyloxy}] bisethanimidothioate, S-methyl N- (methylcarbamoyloxy) thioacetimidate, N, N-dimethyl-2
-Methylcarbamoyloxyimino-2- (methylthio) acetamide, 2- (ethylthiomethyl) phenyl N-methylcarbamate, 2-dimethylamino-5,
Carbamate compounds such as 6-dimethylpyrimidin-4-yl N, N-dimethylcarbamate, 2-sec-butylphenyl N-methylcarbamate;
Nereistoxin derivatives such as S'-2-dimethylaminotrimethylenebis (thiocarbamate), N, N-dimethyl-1,2,3-trithian-5-ylamine;
2,2,2-trichloro-1,1-bis (4-chlorophenyl) ethanol, 4-chlorophenyl-2,4,5
Organic chlorine compounds such as trichlorophenylsulfone; organometallic compounds such as bis [tris (2-methyl-2-phenyl-propyl) tin] oxide;
【0116】(RS)−α−シアノ−3−フェノキシベ
ンジル(RS)−2−(4−クロロフェニル)−3−メ
チルブチレート、3−フェノキシベンジル(1RS)−
シス,トランス−3−(2,2−ジクロロビニル)−
2,2−ジメチルシクロプロパンカルボキシレート、
(RS)−α−シアノ−3−フェノキシベンジル(1R
S)−シス,トランス−3−(2,2−ジクロロビニ
ル)−2,2−ジメチルシクロプロパンカルボキシレー
ト、(S)−α−シアノ−3−フェノキシベンジル(1
R)−シス−3−(2,2−ジブロモビニル)−2,2
−ジメチルシクロプロパンカルボキシレート、(RS)
−α−シアノ−3−フェノキシベンジル(1RS)−シ
ス,トランス−3−(2−クロロ−3,3,3−トリフ
ルオロプロペニル)−2,2−ジメチルシクロプロパン
カルボキシレート、4−メチル−2,3,5,6−テト
ラフルオロベンジル−3−(2−クロロ−3,3,3−
トリフルオロ−1−プロペニル)−2,2−ジメチルシ
クロプロパンカルボキシレート、2−(4−エトキシフ
ェニル)−2−メチルプロピル 3−フェノキシベンジ
ルエーテル(一般名・エトフェンプロックス。以下化合
物No.A−1と略す)のようなピレスロイド系化合
物;(RS) -α-cyano-3-phenoxybenzyl (RS) -2- (4-chlorophenyl) -3-methylbutyrate, 3-phenoxybenzyl (1RS)-
Cis, trans-3- (2,2-dichlorovinyl)-
2,2-dimethylcyclopropane carboxylate,
(RS) -α-cyano-3-phenoxybenzyl (1R
S) -cis, trans-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate, (S) -α-cyano-3-phenoxybenzyl (1
R) -cis-3- (2,2-dibromovinyl) -2,2
-Dimethylcyclopropanecarboxylate, (RS)
-Α-cyano-3-phenoxybenzyl (1RS) -cis, trans-3- (2-chloro-3,3,3-trifluoropropenyl) -2,2-dimethylcyclopropanecarboxylate, 4-methyl-2 , 3,5,6-tetrafluorobenzyl-3- (2-chloro-3,3,3-
Trifluoro-1-propenyl) -2,2-dimethylcyclopropanecarboxylate, 2- (4-ethoxyphenyl) -2-methylpropyl 3-phenoxybenzyl ether (generic name: ethofenprox. Compound No. A- Pyrethroid compounds such as 1);
【0117】1−(4−クロロフェニル)−3−(2,
6−ジフルオロベンゾイル)ウレア、1−〔3,5−ジ
クロロ−4−(3−クロロ−5−トリフルオロメチル−
2−ピリジルオキシ)フェニル〕−3−(2,6−ジフ
ルオロベンゾイル)ウレア、1−(3,5−ジクロロ−
2,4−ジフルオロフェニル)−3−(2,6−ジフル
オロベンゾイル)ウレアのようなベンゾイルウレア系化
合物;イソプロピル(2E,4E)−11−メトキシ−
3,7,11−トリメチル−2,4−ドデカジエノエー
トのような幼若ホルモン様化合物;2−t−ブチル−5
−(4−t−ブチルベンジルチオ)−4−クロロ−3
(2II)−ピリダジノンのようなピリダジノン系化合
物;t−ブチル 4−〔(1,3−ジメチル−5−フェ
ノキシピラゾール−4−イル)メチレンアミノオキシメ
チル〕ベンゾエートのようなピラゾール系化合物;1- (4-chlorophenyl) -3- (2,
6-difluorobenzoyl) urea, 1- [3,5-dichloro-4- (3-chloro-5-trifluoromethyl-
2-pyridyloxy) phenyl] -3- (2,6-difluorobenzoyl) urea, 1- (3,5-dichloro-
Benzoylurea-based compounds such as 2,4-difluorophenyl) -3- (2,6-difluorobenzoyl) urea; isopropyl (2E, 4E) -11-methoxy-
Juvenile hormone-like compounds such as 3,7,11-trimethyl-2,4-dodecadienoate; 2-t-butyl-5
-(4-t-butylbenzylthio) -4-chloro-3
Pyridazinone compounds such as (2II) -pyridazinone; pyrazole compounds such as t-butyl 4-[(1,3-dimethyl-5-phenoxypyrazol-4-yl) methyleneaminooxymethyl] benzoate;
【0118】1−(6−クロロ−3−ピリジルメチル)
−N−ニトロ−イミダゾリジン−2−イリデンアミン
(一般名:イミダクロプリド、以下化合物No.A−2
と略す)、1−〔N−(6−クロロ−3−ピリジルメチ
ル)−N−エチルアミノ〕−1−メチルアミノ−2−ニ
トロエチレン(ヨーロッパ公開No.302389,以
下化合物No.A−3と略す)、2−メチルアミノ−2
−〔N−メチル−N−(6−クロロ−3−ピリジルメチ
ル)アミノ〕−1−ニトロエチレン(ヨーロッパ公開N
o.302389,以下化合物No.A−4と略す)、
1−(6−クロロ−3−ピリジルメチル)アミノ−1−
ジメチルアミノ−2−ニトロエチレン(ヨーロッパ公開
No.302389,以下化合物No.A−5と略
す)、1−(6−クロロ−3−ピリジルメチル)−2−
(1−ニトロ−2−アリルチオエチリデン)イミダゾリ
ジン(ヨーロッパ公開No.437784,以下化合物
No.A−6と略す)、1−(6−クロロ−3−ピリジ
ルメチル)−2−(1−ニトロ−2−エチルチオエチリ
デン)イミダゾリジン(ヨーロッパ公開No.4377
84,以下化合物No.A−7と略す)、1−(6−ク
ロロ−3−ピリジルメチル)−2−(1−ニトロ−2−
β−メチルアリルチオエチリデン)イミダゾリジン(ヨ
ーロッパ公開No.437784,以下化合物No.A
−8と略す)、1−(6−クロロ−3−ピリジルメチ
ル)−3−メチル−2−ニトログアニジン(ヨーロッパ
公開No.383091,以下化合物No.A−9と略
す)、1−(6−クロロ−3−ピリジルメチル)−3,
3−ジメチル−2−ニトログアニジン(ヨーロッパ公開
No.383091,以下化合物No.A−10と略
す)、3−(6−クロロ−3−ピリジルメチル)−2−
ニトロメチレン−チアゾリジン(ヨーロッパ公開No.
192060,以下化合物No.A−11と略す)、1
−(6−クロロ−3−ピリジルメチル)−2−(ニトロ
メチレン)−イミダゾリジン(ヨーロッパ公開No.1
63855,以下化合物No.A−12と略す)、6−
(6−クロロ−3−ピリジルメチルアミノ)−1,3−
ジメチル−5−ニトロ−1,2,3,4−テトラヒドロ
ピリミジン(ヨーロッパ公開No.366085,以下
化合物No.A−13と略す)、1−(6−クロロ−3
−ピリジルメチル)−5−ニトロ−3−メチル−6−メ
チルアミノ−1,2,3,4−テトラヒドロピリミジン
(ヨーロッパ公開No.366085,以下化合物N
o.A−14と略す)などのニトロ系化合物;1- (6-chloro-3-pyridylmethyl)
-N-nitro-imidazolidine-2-ylideneamine (generic name: imidacloprid, hereinafter compound No. A-2)
1- [N- (6-chloro-3-pyridylmethyl) -N-ethylamino] -1-methylamino-2-nitroethylene (European publication No. 302389, hereinafter referred to as compound No. A-3) Abbreviated), 2-methylamino-2
-[N-methyl-N- (6-chloro-3-pyridylmethyl) amino] -1-nitroethylene (Europe published N
o. 302389, hereinafter referred to as Compound No. A-4),
1- (6-chloro-3-pyridylmethyl) amino-1-
Dimethylamino-2-nitroethylene (European publication No. 302389, hereinafter abbreviated as compound No. A-5), 1- (6-chloro-3-pyridylmethyl) -2-
(1-nitro-2-allylthioethylidene) imidazolidine (European publication No. 437784, hereinafter abbreviated as compound No. A-6), 1- (6-chloro-3-pyridylmethyl) -2- (1-nitro -2-ethylthioethylidene) imidazolidine (Europe Publication No. 4377)
84, hereinafter Compound No. A-7), 1- (6-chloro-3-pyridylmethyl) -2- (1-nitro-2-
β-methylallylthioethylidene) imidazolidine (European publication No. 4377784, hereinafter referred to as compound No. A)
-8), 1- (6-chloro-3-pyridylmethyl) -3-methyl-2-nitroguanidine (European publication No. 383091, hereinafter abbreviated as compound No. A-9), 1- (6- Chloro-3-pyridylmethyl) -3,
3-dimethyl-2-nitroguanidine (European publication No. 383091, hereinafter abbreviated as compound No. A-10), 3- (6-chloro-3-pyridylmethyl) -2-
Nitromethylene-thiazolidine (Europe Publication No.
192060, hereinafter referred to as Compound No. A-11), 1
-(6-chloro-3-pyridylmethyl) -2- (nitromethylene) -imidazolidine (European publication No. 1)
No. 63855, Compound No. A-12), 6-
(6-chloro-3-pyridylmethylamino) -1,3-
Dimethyl-5-nitro-1,2,3,4-tetrahydropyrimidine (European publication No. 366085, hereinafter abbreviated as compound No. A-13), 1- (6-chloro-3)
-Pyridylmethyl) -5-nitro-3-methyl-6-methylamino-1,2,3,4-tetrahydropyrimidine (European publication No. 366085, hereinafter referred to as Compound N)
o. Nitro compounds such as A-14);
【0119】ジニトロ系化合物、有機硫黄化合物、尿素
系化合物、トリアジン系化合物、ヒドラジン系化合物、
また、その他の化合物として、2−tert−ブチルイ
ミノ−3−イソプロピル−5−フェニル−3,4,5,
6−テトラヒドロ−2II−1,3,5−チアジアジン
−4−オン(一般名:ププロフェジン、以下化合物N
o.A−15と略す)、トランス−(4−クロロフェニ
ル)−N−シクロヘキシル−4−メチル−2−オキソチ
アゾリジノン−3−カルボキサミド、N−メチルビス
(2,4−キシリルイミノメチル)アミン、N’−(4
−クロロ−o−トリル)−N,N−ジメチルホルムアミ
ジン、(4−エトキシフェニル)−〔3−(4−フルオ
ロ−3−フェノキシフェニル)プロピル〕(ジメチル)
シラン(一般名:シラフルオフェン、以下化合物No.
A−16と略す)のような化合物などが挙げられる。更
に、BT剤、昆虫病原ウイルス剤などのような微生物農
薬、アベルメクチン、ミルベマイシンのような抗生物質
などと、混用、併用することもできる。これらの殺虫
剤、殺ダニ剤及び殺線虫剤のうち、化合物No.A−
1、A−2、A−3、A−4、A−5、A−6、A−
7、A−8、A−9、A−10、A−11、A−12、
A−13、A−14、A−15及びA−16が望まし
く、化合物No.A−1、A−2、A−3、A−6、A
−15及びA−16が更に望ましい。Dinitro compounds, organic sulfur compounds, urea compounds, triazine compounds, hydrazine compounds,
In addition, as other compounds, 2-tert-butylimino-3-isopropyl-5-phenyl-3,4,5,
6-tetrahydro-2II-1,3,5-thiadiazin-4-one (generic name: profofezin, hereinafter compound N)
o. A-15), trans- (4-chlorophenyl) -N-cyclohexyl-4-methyl-2-oxothiazolidinone-3-carboxamide, N-methylbis (2,4-xylyliminomethyl) amine, N '-(4
-Chloro-o-tolyl) -N, N-dimethylformamidine, (4-ethoxyphenyl)-[3- (4-fluoro-3-phenoxyphenyl) propyl] (dimethyl)
Silane (general name: silafluofen, hereinafter referred to as Compound No.
A-16). Further, it can be mixed with or used in combination with a microbial pesticide such as a BT agent or an insect pathogenic virus agent, or an antibiotic such as avermectin or milbemycin. Among these insecticides, acaricides and nematicides, Compound No. A-
1, A-2, A-3, A-4, A-5, A-6, A-
7, A-8, A-9, A-10, A-11, A-12,
A-13, A-14, A-15 and A-16 are desirable, and Compound No. A-1, A-2, A-3, A-6, A
-15 and A-16 are more desirable.
【0120】特に本発明でいう化合物No.9、32、
38、42、60及び210の少なくとも1つと化合物
No.A−1、A−2、A−3、A−6、A−15及び
A−16の少なくとも1つとを混合し、前者が50〜5
000g/ha、後者が10〜5000g/haとなる
よう施用すると、コナガ、コプノメイガ、チャノコカク
モンハマキ、ウンカ類、ヨコバイ類、アブラムシ類など
の有害虫に対し優れた効果を示す。In particular, the compound No. 9, 32,
38, 42, 60 and 210 and Compound No. A-1, A-2, A-3, A-6, A-15, and at least one of A-16 are mixed, and the former is 50 to 5
When the application is performed so as to be 000 g / ha and the latter at 10 to 5000 g / ha, an excellent effect is exhibited against harmful insects such as Japanese moth, Konomeiga mocha, Anopheles rotifer, leafhoppers, leafhoppers and aphids.
【0121】例えば、殺菌剤としては、S−ベンジル
O,O−ジイソプロピルホスホロチオエート、O−エチ
ル S,S−ジフェニルホスホロジチオエート、アルミ
ニウムエチルハイドロゲンホスホネートのような有機リ
ン系化合物;4,5,6,7−テトラクロロフタリド、
テトラクロロイソフタロニトリルのような有機塩素系化
合物;マンガニーズエチレンビス(ジチオカーバメー
ト)の重合物、ジンクエチレンビス(ジチオカーバメー
ト)の重合物、ジンクとマンガニーズエチレンビス(ジ
チオカーバメート)との錯化合物、ジジンクビス(ジメ
チルジチオカーバメート)エチレンビス(ジチオカーバ
メート)、ジンクプロピレンビス(ジチオカーバメー
ト)の重合物のようなジチオカーバメート系化合物;For example, as a bactericide, S-benzyl
Organic phosphorus compounds such as O, O-diisopropyl phosphorothioate, O-ethyl S, S-diphenyl phosphorodithioate, aluminum ethyl hydrogen phosphonate; 4,5,6,7-tetrachlorophthalide;
Organochlorine compounds such as tetrachloroisophthalonitrile; polymers of manganese ethylenebis (dithiocarbamate), polymers of zinc ethylenebis (dithiocarbamate), complex compounds of zinc and manganese ethylenebis (dithiocarbamate) A dithiocarbamate compound such as a polymer of dizincbis (dimethyldithiocarbamate), ethylenebis (dithiocarbamate), and zinc propylenebis (dithiocarbamate);
【0122】3a,4,7,7a−テトラヒドロ−N−
(トリクロロメチルスルフェニル)フタルイミド、3
a,4,7,7a−テトラヒドロ−N−(1,1,2,
2,−テトラクロロエチルスルフェニル)フタルイミ
ド、N−(トリクロロメチルスルフェニル)フタルイミ
ドのようなN−ハロゲノチオアルキル系化合物;3−
(3,5−ジクロロフェニル)−N−イソプロピル−
2,4−ジオキソイミダゾリジン−1−カルボキサミ
ド、(RS)−3−(3,5−ジクロロフェニル)−5
−メチル−5−ビニル−1,3−オキサゾリジン−2,
4−ジオン、N−(3,5−ジクロロフェニル)−1,
2−ジメチルシクロプロパン−1,2−ジカルボキシミ
ドのようなジカルボキシミド系化合物;3a, 4,7,7a-Tetrahydro-N-
(Trichloromethylsulfenyl) phthalimide, 3
a, 4,7,7a-tetrahydro-N- (1,1,2,2
N-halogenothioalkyl compounds such as 2, -tetrachloroethylsulfenyl) phthalimide and N- (trichloromethylsulfenyl) phthalimide;
(3,5-dichlorophenyl) -N-isopropyl-
2,4-dioxoimidazolidin-1-carboxamide, (RS) -3- (3,5-dichlorophenyl) -5
-Methyl-5-vinyl-1,3-oxazolidine-2,
4-dione, N- (3,5-dichlorophenyl) -1,
Dicarboximide compounds such as 2-dimethylcyclopropane-1,2-dicarboximide;
【0123】メチル 1−(ブチルカルバモイル)ベン
ズイミダゾール−2−イルカーバメート、ジメチル4,
4’−(o−フェニレン)ビス(3−チオアロファネー
トのようなベンズイミダゾール系化合物;1−(4−ク
ロロフェノキシ)−3,3−ジメチル−1−(1H−
1,2,4−トリアゾール−1−イル)ブタノン、1−
(ビフェニイル−4−イルオキシ)−3,3−ジメチル
−1−(1H−1,2,4−トリアゾール−1−イル)
ブタン−2−オール、1−〔N−(4−クロロ−2−ト
リフルオロメチルフェニル)−2−プロポキシアセトイ
ミドイル〕イミダゾール、1−〔2−(2,4−ジクロ
ロフェニル)−4−エチル−1,3−ジオキソラン−2
−イルメチル〕−1H−1,2,4−トリアゾール、1
−〔2−(2,4−ジクロロフェニル)−4−プロピル
−1,3−ジオキソラン−2−イルメチル〕−1H−
1,2,4−トリアゾール、1−〔2−(2,4−ジク
ロロフェニル)ペンチル〕−1H−1,2,4−トリア
ゾールのようなアゾール系化合物;2,4’−ジクロロ
−α−(ピリミジン−5−イル)ベンズヒドリルアルコ
ール、(±)−2,4’−ジフルオロ−α−(1H−
1,2,4−トリアゾール−1−イルメチル)ベンズヒ
ドリルアルコールのようなカルビノール系化合物;Methyl 1- (butylcarbamoyl) benzimidazol-2-ylcarbamate, dimethyl 4,
Benzimidazole compounds such as 4 '-(o-phenylene) bis (3-thioallophanate; 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-
1,2,4-triazol-1-yl) butanone, 1-
(Biphenyl-4-yloxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl)
Butan-2-ol, 1- [N- (4-chloro-2-trifluoromethylphenyl) -2-propoxyacetimidoyl] imidazole, 1- [2- (2,4-dichlorophenyl) -4-ethyl- 1,3-dioxolan-2
-Ylmethyl] -1H-1,2,4-triazole, 1
-[2- (2,4-dichlorophenyl) -4-propyl-1,3-dioxolan-2-ylmethyl] -1H-
Azole compounds such as 1,2,4-triazole, 1- [2- (2,4-dichlorophenyl) pentyl] -1H-1,2,4-triazole; 2,4′-dichloro-α- (pyrimidine -5-yl) benzhydryl alcohol, (±) -2,4′-difluoro-α- (1H-
Carbinol compounds such as (1,2,4-triazol-1-ylmethyl) benzhydryl alcohol;
【0124】3’−イソプロポキシ−o−トリアニリ
ド、α,α,α−トリフルオロ−3’−イソプロポキシ
−o−トルアニリドのようなベンズアニリド系化合物;
メチルN−(2−メトキシアセチル)−N−(2,6−
キシリル)−DL−アラニネートのようなフェニルアミ
ド系化合物;3−クロロ−N−(3−クロロ−2,6−
ジニトロ−4−α,α,α−トリフルオロトリル)−5
−トリフルオロメチル−2−ピリジナミンのようなピリ
ジナミン系化合物;ピペラジン系化合物、モルフォリン
系化合物、アントラキノン系化合物、キノキサリン系化
合物、クロトン酸系化合物、スルフェン酸系化合物、尿
素系化合物、またその他の化合物として、ジイソプロピ
ル−1,3−ジチオラン−2−イリデン−マロネート、
5−メチル−1,2,4−トリアゾロ〔3,4−b〕ベ
ンチアゾール、1,2,5,6−テトラヒドロピロロ
〔3,2,1−ij〕キノリン−4−オン、6−(3,
5−ジクロロ−4−メチルフェニル)−3(2H)−ピ
リダジノン、3−アリルオキシ−1,2−ベンゾイソチ
アゾール−1,1−ジオキシド、1−(4−クロロベン
ジル)−1−シクロペンチル−3−フェニル尿素のよう
な化合物;などが挙げられる。さらにバリダマイシンA
のような抗生物物などと混用、併用することもできる。Benzanilide compounds such as 3'-isopropoxy-o-trianilide and α, α, α-trifluoro-3'-isopropoxy-o-toluanilide;
Methyl N- (2-methoxyacetyl) -N- (2,6-
Phenylamide compounds such as xylyl) -DL-alaninate; 3-chloro-N- (3-chloro-2,6-
Dinitro-4-α, α, α-trifluorotolyl) -5
Pyridinamine compounds such as trifluoromethyl-2-pyridinamine; piperazine compounds, morpholine compounds, anthraquinone compounds, quinoxaline compounds, crotonic acid compounds, sulfenic acid compounds, urea compounds, and other compounds As diisopropyl-1,3-dithiolan-2-ylidene-malonate;
5-methyl-1,2,4-triazolo [3,4-b] benzazole, 1,2,5,6-tetrahydropyrrolo [3,2,1-ij] quinolin-4-one, 6- (3 ,
5-dichloro-4-methylphenyl) -3 (2H) -pyridazinone, 3-allyloxy-1,2-benzisothiazole-1,1-dioxide, 1- (4-chlorobenzyl) -1-cyclopentyl-3- Compounds such as phenylurea; and the like. Further validamycin A
Can be mixed and used in combination with antibiotics such as.
【0125】本発明化合物と他の農薬との混合割合は、
1:100〜100:1、望ましくは1:50〜50:
1である。本発明でいう化合物を有効成分として含有す
る有害生物防除剤の施用は、一般に1〜100,000
ppm、望ましくは1〜50,000ppmさらに望ま
しくは10〜20,000ppmの有効成分濃度で行な
う。これらの有効成分濃度は、製剤の形態及び施用する
方法、目的、時間、場所及び害虫の発生状況等によって
これらの範囲を逸脱してもよい。例えば、水生有害虫の
場合、上記濃度範囲の薬液を発生場所に散布しても防除
できることから、水中での有効成分濃度範囲は上記以下
である。単位面積あたりの施用量は1ha当り、有効成
分化合物として約1〜50000g、望ましくは10〜
10000gさらに望ましくは、50〜5000gが使
用される。しかし、特別の場合には、これらの範囲を逸
脱することも可能である。また、その施用は、通常一般
に行なわれている方法、即ち、散布(例えば散布、噴
霧、ミスティング、アトマイジング、散粒、水面施用
等)、土壌施用(混入、灌注等)、表面施用(塗布、粉
衣、被覆等)、浸漬毒餌等により行うことができる。ま
た、家畜に対して前記有効成分を飼料に混合して与え、
その排泄物での有害虫、特に有害昆虫の発生成育を防除
することも可能である。またいわゆる微量散布法(ul
tra low Volume)により施用することも
できる。この方法においては、活性成分を100%含有
することが可能である。The mixing ratio of the compound of the present invention to other pesticides is as follows:
1: 100 to 100: 1, desirably 1:50 to 50:
It is one. The application of the pesticidal composition containing the compound of the present invention as an active ingredient is generally from 1 to 100,000.
ppm, preferably 1 to 50,000 ppm, more preferably 10 to 20,000 ppm. The concentration of these active ingredients may deviate from these ranges depending on the form of the preparation, the method of application, the purpose, the time, the place and the occurrence of pests. For example, in the case of aquatic pests, even if a chemical solution having the above-mentioned concentration range is sprayed at the place of occurrence, control can be carried out. The application rate per unit area is about 1 to 50000 g, preferably 10 to 10 g, as an active ingredient compound per ha.
10,000 g and more preferably 50 to 5000 g are used. However, in special cases, it is possible to deviate from these ranges. In addition, the application is usually carried out in a generally practiced manner, that is, spraying (eg, spraying, spraying, misting, atomizing, granulation, water surface application, etc.), soil application (mixing, irrigation, etc.), surface application (application) , Dressing, coating, etc.), dipping poison bait and the like. Further, the livestock is fed with the active ingredient mixed with feed,
It is also possible to control the development and growth of harmful insects, especially harmful insects, in the excrement. The so-called micro-spraying method (ul
(tra low Volume). In this method, it is possible to contain 100% of the active ingredient.
【0126】試験例1 ハスモンヨトウ殺虫試験 有効成分化合物のそれぞれの製剤品を水に分散させて8
00ppmの濃度に調整した薬液にキャベツの葉片を約
10秒間浸漬し、風乾した。直径9cmのペトリ皿に湿
った濾紙を敷き、その上に風乾した葉片を置いた。そこ
へ2〜3令のハスモンヨトウ幼虫10頭を放ち、ふたを
して26℃の照明付恒温器内に放置した。放虫後5日目
に生死を判定し、下記計算式により死虫率を求めた。 死虫率(%)=(死虫数÷放虫数)×100 前記化合物No.1、2、4〜12、15、17、30
〜34、36〜39、42、43、45、47〜49、
51、53、55〜62、74、201、202、21
0〜215、221、224、225及び303は死虫
率100%を示し、化合物No.20、65、200及
び304は死虫率90%を示した。 Test Example 1 Spodoptera litura Insecticidal Test Each preparation of the active ingredient compound was dispersed in water to give 8
Cabbage leaf pieces were immersed in a chemical solution adjusted to a concentration of 00 ppm for about 10 seconds, and air-dried. A wet filter paper was spread on a petri dish having a diameter of 9 cm, and air-dried leaf pieces were placed thereon. Thereto were released 10 to 3 larvae of the cutworm cutworm, which were capped and left in a 26 ° C. illuminated incubator. On the 5th day after the release, the survival was determined, and the mortality was determined by the following formula. Mortality (%) = (number of dead insects / number of released insects) × 100 1, 2, 4 to 12, 15, 17, 30
~ 34, 36-39, 42, 43, 45, 47-49,
51, 53, 55-62, 74, 201, 202, 21
Nos. 0 to 215, 221, 224, 225 and 303 show a mortality of 100%. 20, 65, 200 and 304 showed a mortality of 90%.
【0127】試験例2 コナガ殺虫試験 2〜3令のハスモンヨトウを2〜3令のコナガに代える
こと以外は前記試験例1の場合と同様にして試験を行な
い、死虫率を求めた。前記化合物No.1、2、4、
5、7〜12、30、32、34、38、39、41〜
45、49、60、61、201、202、210、2
13及び301は死虫率100%を示した。 Test Example 2 Insect Insecticidal Test A test was conducted in the same manner as in Test Example 1 except that the cutworm, Spodoptera litura, 2-3 years old was replaced with a 2-3 year old moth, and the mortality was determined. The compound No. 1, 2, 4,
5, 7-12, 30, 32, 34, 38, 39, 41-
45, 49, 60, 61, 201, 202, 210, 2
13 and 301 showed a mortality of 100%.
【0128】試験例3 コブノメイガ殺虫試験 有効成分化合物のそれぞれの製剤品を水に分散させて8
00ppmの濃度に調整した薬液にトウモロコシの葉片
を約10秒間浸漬し、風乾した。直径8cmのアイスク
リームカップに湿った濾紙を敷き、その上に風乾した葉
片を置いた。そこへ2〜3令のコブノメイガ幼虫5頭を
放ち、ふたをして26℃の照明付恒温器内に放置した。
放虫後5日目に生死を判定し前記試験例1の場合と同様
にして死虫率を求めた。化合物No.9、32〜34、
38、210及び211は死虫率100%を示した。 Test Example 3 Test for Insecticidal Test of Kobumemeiga Each of the active ingredient compounds was dispersed in water to give 8
Corn leaf pieces were immersed in a chemical solution adjusted to a concentration of 00 ppm for about 10 seconds and air-dried. A wet filter paper was spread over an ice cream cup having a diameter of 8 cm, and air-dried leaf pieces were placed thereon. There were released five 2-3-year-old larvae of the larvae of Kobumemeiga, which were capped and left in a 26 ° C. illuminated incubator.
On the 5th day after the release, the survival was determined, and the mortality was determined in the same manner as in Test Example 1. Compound No. 9, 32-34,
38, 210 and 211 showed a mortality of 100%.
【0129】試験例4 チャノコカクモンハマキ殺虫試
験 有効成分化合物のそれぞれの製剤品を水に分散させて8
00ppmの濃度に調整した薬液に人工飼料〔商品名:
インセクタ.LFR(日本農産工業(株))〕の小片を
60秒間浸漬した後、約1時間、室内に放置した。直径
8cmのアイスクリームカップに濾紙を敷き、その上に
処理した前記人工飼料を置いた。そこへ2〜3令のチャ
ノコカクモンハマキ幼虫10頭を放ち、ふたをして26
℃の照明付恒温器内に放置した。放虫後8〜9日目に生
死を判定し、前記試験例1の場合と同様にして死虫率を
求めた。化合物No.9、32、38、42、60及び
210は死虫率100%を示した。 Test Example 4 Insecticidal test of Anopheles japonicus
Each formulation of the test active ingredient compound was dispersed in water to give 8
An artificial feed [trade name:
In sector. A small piece of LFR (Nihon Nosan Kogyo Co., Ltd.) was immersed for 60 seconds, and then left indoor for about 1 hour. Filter paper was spread over an ice cream cup having a diameter of 8 cm, and the treated artificial feed was placed thereon. There, 10 larvae of the 2-3 year old larvae were released, covered, and 26
It was left in a thermostat with illumination at ℃. On the 8th to 9th days after the release, survival was determined, and the mortality was determined in the same manner as in Test Example 1. Compound No. 9, 32, 38, 42, 60 and 210 showed a mortality of 100%.
【0130】試験例5 ウリハムシ殺虫試験 有効成分化合物のそれぞれの製剤品を水に分散させて8
00ppmの濃度に調整した薬液にキュウリの葉片を約
10秒間浸漬し、風乾した。直径8cmのアイスクリー
ムカップに湿った濾紙を敷き、その上に風乾した葉片を
置いた。そこへウリハムシ成虫5頭を放ち、ふたをして
26℃の照明付恒温器内に放置した。放虫後5日目に生
死を判定し、前記試験例1の場合と同様にして死虫率を
求めた。化合物No.9は死虫率100%を示した。 Test Example 5 Insecticidal test of beetle beetle Each preparation of the active ingredient compound was dispersed in water to give 8
Cucumber leaf pieces were immersed in a chemical solution adjusted to a concentration of 00 ppm for about 10 seconds and air-dried. A wet filter paper was spread over an ice cream cup having a diameter of 8 cm, and air-dried leaf pieces were placed thereon. Five adult beetles were released there, covered, and left in a 26 ° C. illuminated thermostat. On the 5th day after the release, survival was determined, and the mortality was determined in the same manner as in Test Example 1. Compound No. 9 showed a mortality of 100%.
【0131】[0131]
【発明の効果】本発明によれば優れた有害生物防除活性
を示す新規ヒドラゾン系化合物並びにヒドラゾン系化合
物を含有する有害生物防除剤が提供される。According to the present invention, there is provided a novel hydrazone compound having excellent pest control activity and a pesticide containing the hydrazone compound.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 FI C07C 257/22 C07C 257/22 281/04 281/04 (72)発明者 佐々木 広志 滋賀県草津市西渋川二丁目3番1号 石 原産業株式会社 中央研究所内 (72)発明者 森田 雅之 滋賀県草津市西渋川二丁目3番1号 石 原産業株式会社 中央研究所内 (72)発明者 米田 哲夫 滋賀県草津市西渋川二丁目3番1号 石 原産業株式会社 中央研究所内 審査官 爾見 武志 (56)参考文献 特開 平2−142777(JP,A) 特開 平5−4958(JP,A) 特表 平6−502414(JP,A) 欧州特許出願公開462456(EP,A 1) (58)調査した分野(Int.Cl.7,DB名) C07C 251/86 C07C 251/88 C07C 257/22 C07C 281/04 A01N 35/10 A01N 37/52 A01N 47/12 CA(STN) REGISTRY(STN)────────────────────────────────────────────────── ─── Continued on the front page (51) Int.Cl. 7 Identification code FI C07C 257/22 C07C 257/22 281/04 281/04 (72) Inventor Hiroshi Sasaki 2-3-1 Nishi-Shibukawa, Kusatsu City, Shiga Prefecture No.Ishihara Sangyo Co., Ltd., Central Research Laboratory (72) Inventor Masayuki Morita 2-3-1 Nishi-Shibukawa, Kusatsu-shi, Shiga Prefecture In-Central Research Laboratory (72) Inventor Tetsuo Yoneda Nishi-Shibukawa, Kusatsu-shi, Shiga No.3-1, Ishihara Sangyo Co., Ltd. Examiner in Central Research Laboratory Takeshi Nimi (56) References JP-A-2-142777 (JP, A) JP-A-5-4958 (JP, A) 502414 (JP, A) European Patent Application Publication 462456 (EP, A1) (58) Fields investigated (Int. Cl. 7 , DB name) C07C 251/86 C07C 251/88 C07C 257/22 C07C 281/04 A01N 35/10 A01N 37/52 A01N 47/12 CA (STN ) REGISTRY (STN)
Claims (7)
子、ハロゲン原子、ハロゲン原子で置換されてもよいア
ルキル基又はハロゲン原子で置換されてもよいアルコキ
シ基であり、R 3 はハロゲン原子、ハロゲン原子で置換
されてもよいアルキル基又はハロゲン原子で置換されて
もよいアルコキシ基であり、R 5 は水素原子又はアルキ
ル基であり、R 6 はX 7 CO−基又はX 8 OCO−基で
あるか又はR 5 とR 6 が一緒になって、=CR 7 R 8 基
を形成してもよく、X 7 は水素原子又はアルキル基であ
り、X 8 はアルキル基であり、R 7 は水素原子又はアル
キル基であり、R 8 はアルキル基で置換されてもよいア
ミノ基又はアルコキシ基である。但し、各置換基が以下
の(1)〜(3)である場合を除く。(1)R2、R4
及びR5が水素原子であり、R6がエトキシカルボニル
基であり、かつR1及びR3の少くとも1つがp−メト
キシ基である場合、(2)R1、R2、R4及びR5が
水素原子であり、R3がp−ターシャリーブチル基であ
り、かつR6がエトキシカルボニル基である場合、
(3)R1、R2及びR4が水素原子であり、R3がp
−弗素原子であり、R5がイソプロピル基であり、かつ
R6が水素原子又はアセチル基である場合。)で表わさ
れるヒドラゾン系化合物又はそれらの塩。1. A compound of the general formula (I): ( Wherein R 1 , R 2 and R 4 are each independently a hydrogen atom
, A halogen atom, an atom which may be substituted with a halogen atom.
Alkoxy which may be substituted by alkyl group or halogen atom
R 3 is a halogen atom, substituted with a halogen atom
Substituted with an alkyl group or a halogen atom which may be
And R 5 is a hydrogen atom or an alkyl group.
And R 6 is an X 7 CO— group or an X 8 OCO— group.
Or R 5 and R 6 together form a = CR 7 R 8 group
And X 7 is a hydrogen atom or an alkyl group.
X 8 is an alkyl group; R 7 is a hydrogen atom or
R 8 is an alkyl group which may be substituted with an alkyl group.
It is a mino group or an alkoxy group. However, the case where each substituent is the following (1) to (3) is excluded. (1) R 2 , R 4
And R 5 is a hydrogen atom, R 6 is an ethoxycarbonyl group, and at least one of R 1 and R 3 is a p-methoxy group; (2) R 1 , R 2 , R 4 and R When 5 is a hydrogen atom, R 3 is a p-tert-butyl group, and R 6 is an ethoxycarbonyl group,
(3) R 1 , R 2 and R 4 are hydrogen atoms, and R 3 is p
-A fluorine atom, R 5 is an isopropyl group and R 6 is a hydrogen atom or an acetyl group. Or a salt thereof.
(I)で表わされる化合物が〔4’−クロロ−2−(4
−トリフルオロメチルフェニル)アセトフェノン〕N’
−〔1−(ジメチルアミノ)エチリデン〕ヒドラゾン、
〔4’−フルオロ−2−(4−トリフルオロメチルフェ
ニル)アセトフェノン〕N’−〔1−(ジメチルアミ
ノ)エチリデン〕ヒドラゾン、エチル3−〔1−(4−
クロロフェニル)−2−(4−トリフルオロメチルフェ
ニル)エチリデン〕カーバゼート、〔4’−クロロ−2
−(4−ターシャリーブチルフェニル)アセトフェノ
ン〕N’−〔1−(ジメチルアミノ)エチリデン〕ヒド
ラゾン及び〔4’−フルオロ−2−(4−ターシャリー
ブチルフェニル)アセトフェノン〕N’−〔1−(ジメ
チルアミノ)エチリデン〕ヒドラゾンからなる群から選
ばれた少なくとも1つの化合物であるヒドラゾン系化合
物。2. The compound according to claim 1, wherein the compound represented by the general formula (I) is [4′-chloro-2- (4
-Trifluoromethylphenyl) acetophenone] N '
-[1- (dimethylamino) ethylidene] hydrazone,
[4'-Fluoro-2- (4-trifluoromethylphenyl) acetophenone] N '-[1- (dimethylamino) ethylidene] hydrazone, ethyl 3- [1- (4-
Chlorophenyl) -2- (4-trifluoromethylphenyl) ethylidene] carbazate, [4′-chloro-2]
-(4-tert-butylphenyl) acetophenone] N '-[1- (dimethylamino) ethylidene] hydrazone and [4'-fluoro-2- (4-tert-butylphenyl) acetophenone] N'-[1- ( A hydrazone compound which is at least one compound selected from the group consisting of [dimethylamino) ethylidene] hydrazone.
子、ハロゲン原子、ハロゲン原子で置換されてもよいア
ルキル基又はハロゲン原子で置換されてもよいアルコキ
シ基であり、R 3 はハロゲン原子、ハロゲン原子で置換
されてもよいアルキル基又はハロゲン原子で置換されて
もよいアルコキシ基であり、R 5 は水素原子又はアルキ
ル基であり、R 6 はX 7 CO−基又はX 8 OCO−基で
あるか又はR 5 とR 6 が一緒になって、=CR 7 R 8 基
を形成してもよく、X 7 は水素原子又はアルキル基であ
り、X 8 はアルキル基であり、R 7 は水素原子又はアル
キル基であり、R 8 はアルキル基で置換されてもよいア
ミノ基又はアルコキシ基である。但し、各置換基が以下
の(1)〜(3)である場合を除く。(1)R2、R4
及びR5が水素原子であり、R6がエトキシカルボニル
基であり、かつR1及びR3の少くとも1つがp−メト
キシ基である場合、(2)R1、R2、R4及びR5が
水素原子であり、R3がp−ターシャリーブチル基であ
り、かつR6がエトキシカルボニル基である場合、
(3)R1、R2及びR4が水素原子であり、R3がp
−弗素原子であり、R5がイソプロピル基であり、かつ
R6が水素原子又はアセチル基である場合。)で表わさ
れるヒドラゾン系化合物又はそれらの塩の製造方法であ
って、一般式(II): 【化3】 (式中、R1、R2、R3及びR4は前述の通りであ
る)で表わされる化合物と一般式(III): 【化4】 (式中、R5及びR6は前述の通りである)で表わされ
る化合物とを反応させることを特徴とするヒドラゾン系
化合物又はそれらの塩の製造方法。3. A compound of the general formula (I): ( Wherein R 1 , R 2 and R 4 are each independently a hydrogen atom
, A halogen atom, an atom which may be substituted with a halogen atom.
Alkoxy which may be substituted by alkyl group or halogen atom
R 3 is a halogen atom, substituted with a halogen atom
Substituted with an alkyl group or a halogen atom which may be
And R 5 is a hydrogen atom or an alkyl group.
And R 6 is an X 7 CO— group or an X 8 OCO— group.
Or R 5 and R 6 together form a = CR 7 R 8 group
And X 7 is a hydrogen atom or an alkyl group.
X 8 is an alkyl group; R 7 is a hydrogen atom or
R 8 is an alkyl group which may be substituted with an alkyl group.
It is a mino group or an alkoxy group. However, the case where each substituent is the following (1) to (3) is excluded. (1) R 2 , R 4
And R 5 is a hydrogen atom, R 6 is an ethoxycarbonyl group, and at least one of R 1 and R 3 is a p-methoxy group; (2) R 1 , R 2 , R 4 and R When 5 is a hydrogen atom, R 3 is a p-tert-butyl group, and R 6 is an ethoxycarbonyl group,
(3) R 1 , R 2 and R 4 are hydrogen atoms, and R 3 is p
-A fluorine atom, R 5 is an isopropyl group and R 6 is a hydrogen atom or an acetyl group. A method for producing a hydrazone compound represented by the formula (I) or a salt thereof, which comprises the general formula (II): Wherein R 1 , R 2 , R 3 and R 4 are as described above, and a compound represented by the general formula (III): (Wherein R 5 and R 6 are as defined above). A process for producing a hydrazone-based compound or a salt thereof.
子、ハロゲン原子、ハロゲン原子で置換されてもよいア
ルキル基又はハロゲン原子で置換されてもよいアルコキ
シ基であり、R 3 はハロゲン原子、ハロゲン原子で置換
されてもよいアルキル基又はハロゲン原子で置換されて
もよいアルコキシ基であり、R 7 は水素原子又はアルキ
ル基であり、R 8 はアルキル基で置換されてもよいアミ
ノ基又はアルコキシ基である)で表わされるヒドラゾン
系化合物又はそれらの塩の製造方法であって、一般式
(I−2): 【化6】 (式中、R1、R2、R3及びR4は前述の通りであ
る)で表わされる化合物と一般式(IV): 【化7】 (式中、R7及びR8は前述の通りであり、J1はアル
キル基である)で表わされる化合物とを反応させること
を特徴とするヒドラゾン系化合物又はそれらの塩の製造
方法。4. A compound of the general formula (I-1): ( Wherein R 1 , R 2 and R 4 are each independently a hydrogen atom
, A halogen atom, an atom which may be substituted with a halogen atom.
Alkoxy which may be substituted by alkyl group or halogen atom
R 3 is a halogen atom, substituted with a halogen atom
Substituted with an alkyl group or a halogen atom which may be
And R 7 is a hydrogen atom or an alkyl group.
R 8 is an amino group which may be substituted with an alkyl group.
Hydrazone compound represented by Bruno is a group or an alkoxy group), or a method for producing a salt thereof, the general formula (I-2): embedded image Wherein R 1 , R 2 , R 3 and R 4 are as described above, and a compound represented by the general formula (IV): (Wherein R 7 and R 8 are as described above, and J 1 is an alkyl group). A process for producing a hydrazone compound or a salt thereof, which comprises reacting the compound with the compound represented by the formula:
子、ハロゲン原子、ハロゲン原子で置換されてもよいア
ルキル基又はハロゲン原子で置換されてもよいアルコキ
シ基であり、R 3 はハロゲン原子、ハロゲン原子で置換
されてもよいアルキル基又はハロゲン原子で置換されて
もよいアルコキシ基であり、R 7 は水素原子又はアルキ
ル基であり、J 2 及びJ 3 は各々独立して、水素原子又
はアルキル基である)で表わされるヒドラゾン系化合物
又はそれらの塩の製造方法であって、一般式(VI): 【化9】 (式中、R1、R2、R3、R4及びR7は前述の通り
である)で表わされる化合物又は一般式(VIII): 【化10】 (式中、R1、R2、R3、R4及びR7は前述の通り
である)で表わされる化合物と、一般式(VII): 【化11】 (式中、J2及びJ3は前述の通りである)で表わされ
る化合物とを反応させることを特徴とするヒドラゾン系
化合物又はそれらの塩の製造方法。5. A compound of the general formula (I-4): ( Wherein R 1 , R 2 and R 4 are each independently a hydrogen atom
, A halogen atom, an atom which may be substituted with a halogen atom.
Alkoxy which may be substituted by alkyl group or halogen atom
R 3 is a halogen atom, substituted with a halogen atom
Substituted with an alkyl group or a halogen atom which may be
And R 7 is a hydrogen atom or an alkyl group.
And J 2 and J 3 are each independently a hydrogen atom or
Is an alkyl group ), or a hydrazone compound represented by the general formula (VI): Wherein R 1 , R 2 , R 3 , R 4 and R 7 are as defined above, or a compound of the general formula (VIII): Wherein R 1 , R 2 , R 3 , R 4 and R 7 are as described above, and a compound represented by the general formula (VII): (Wherein J 2 and J 3 are as described above), and a method for producing a hydrazone-based compound or a salt thereof.
らの塩を含有することを特徴とする有害生物防除剤。6. A pesticidal composition comprising the hydrazone compound according to claim 1 or a salt thereof.
らの塩の有効量を施用することを特徴とする有害生物防
除方法。7. A method for controlling pests, which comprises applying an effective amount of the hydrazone compound of claim 1 or a salt thereof.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP07940292A JP3330155B2 (en) | 1991-02-22 | 1992-02-15 | Hydrazone-based compounds, methods for their production, intermediates for their production, and pesticides containing them |
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11419191 | 1991-02-22 | ||
JP6438892 | 1992-02-04 | ||
JP4-64388 | 1992-02-04 | ||
JP3-114191 | 1992-02-04 | ||
JP07940292A JP3330155B2 (en) | 1991-02-22 | 1992-02-15 | Hydrazone-based compounds, methods for their production, intermediates for their production, and pesticides containing them |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH05279312A JPH05279312A (en) | 1993-10-26 |
JP3330155B2 true JP3330155B2 (en) | 2002-09-30 |
Family
ID=27298470
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP07940292A Expired - Lifetime JP3330155B2 (en) | 1991-02-22 | 1992-02-15 | Hydrazone-based compounds, methods for their production, intermediates for their production, and pesticides containing them |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP3330155B2 (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4626731B2 (en) * | 1999-07-05 | 2011-02-09 | 日本農薬株式会社 | Anticide and method of use |
CN1537091A (en) | 2001-08-03 | 2004-10-13 | 石原产业株式会社 | Method for producing 2-phenylacetophenone derivative, and precursor for producng the same |
JP4792199B2 (en) * | 2002-10-07 | 2011-10-12 | 石原産業株式会社 | House pest control composition and control method |
WO2005053408A1 (en) * | 2003-12-03 | 2005-06-16 | Ishihara Sangyo Kaisha, Ltd. | Composition for controlling pests and metmhod of controlling pests |
JP4745651B2 (en) * | 2003-12-03 | 2011-08-10 | 石原産業株式会社 | Pest control composition and pest control method |
FR2904311B1 (en) * | 2006-07-28 | 2013-01-11 | Clariant Specialty Fine Chem F | NEW PROCESS FOR THE SYNTHESIS OF (E) STILBENIC DERIVATIVES PERM TO OBTAIN RESVERATROL AND PICEATANNOL |
-
1992
- 1992-02-15 JP JP07940292A patent/JP3330155B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
JPH05279312A (en) | 1993-10-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2994182B2 (en) | Amide compounds or salts thereof, methods for producing them and pest control agents containing them | |
RU2051902C1 (en) | Hydrazine derivatives or salts thereof | |
US5288727A (en) | Hydrazone compounds, processes for their production, intermediates useful for their production and pesticidal compositions containing them | |
JP2606720B2 (en) | Imidazole compounds and pesticides containing them | |
JPH0710841A (en) | 4-trifluoromethylpyridine-3-carboxamide compound or salt thereof, their production and pest-controlling agent containing the same | |
WO2000023422A1 (en) | Hydrazinooxoacetamide derivatives and insecticide | |
JP3330155B2 (en) | Hydrazone-based compounds, methods for their production, intermediates for their production, and pesticides containing them | |
JPH066597B2 (en) | Organophosphorus compounds, methods for producing them, and insecticidal, acaricidal, nematicidal, and soil-pesticidal composition containing them | |
JP4121158B2 (en) | Disease or pest control agent comprising an alkoxyimino-substituted bicyclic derivative as an active ingredient | |
JPH03141245A (en) | Hydrazine-based compound, production thereof and controlling agent against noxious animal containing the same | |
JPH10101648A (en) | Amide based compound or it salt, their production and noxious insetct controller containing the same | |
JPH023659A (en) | Benzoylurea based compound, production thereof and noxious animal controlling agent containing the same compound | |
JPH07138233A (en) | Hydrazone-based compound or its salt, production therefor and pest control agent containing the same as the active component | |
JPH02207066A (en) | Hydrazine-based compound, production thereof and controller against harmful animal containing same | |
JPH026496A (en) | Organic phosphoric acid amide compound, its production and harmful animal-controlling agent containing the same compound | |
JPH02129173A (en) | Triazole compound, its production and harmful life controlling agent containing the same | |
JP3330152B2 (en) | Hydrazine compounds, their production method and pest control agents containing them | |
JPS6348268A (en) | N-pyridyl-n'-benzoylurea compound and insecticide containing said compound | |
JPH0296568A (en) | Pyrazole compound, preparation thereof and pest control agent containing the same compound | |
JP3005300B2 (en) | Imidazolidine derivatives, their production methods and pesticidal agents containing them | |
JP2577712B2 (en) | Imidazo [4,5-b] pyridine compounds and pesticides containing them | |
JPS62155248A (en) | N-benzoyl-n'-phenylurea compound and insecticide containing same | |
JPS62155260A (en) | N-benzoyl-n'-pyridylurea and insecticide containing same | |
JPH066598B2 (en) | Organophosphorus compounds and insecticides, acaricides, nematicides, and soil insecticides containing them | |
JP2526037B2 (en) | Intermediate of imidazo [4,5-b] pyridine compound |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20080719 Year of fee payment: 6 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090719 Year of fee payment: 7 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20100719 Year of fee payment: 8 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20100719 Year of fee payment: 8 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110719 Year of fee payment: 9 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120719 Year of fee payment: 10 |
|
EXPY | Cancellation because of completion of term | ||
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120719 Year of fee payment: 10 |