JP2879174B2 - Hydrazone derivatives, their production, their uses and their use - Google Patents
Hydrazone derivatives, their production, their uses and their useInfo
- Publication number
- JP2879174B2 JP2879174B2 JP32951891A JP32951891A JP2879174B2 JP 2879174 B2 JP2879174 B2 JP 2879174B2 JP 32951891 A JP32951891 A JP 32951891A JP 32951891 A JP32951891 A JP 32951891A JP 2879174 B2 JP2879174 B2 JP 2879174B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- same
- different
- haloalkyl
- halogen atom
- 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 - Fee Related
Links
- 150000007857 hydrazones Chemical class 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 125000001188 haloalkyl group Chemical group 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000005843 halogen group Chemical group 0.000 claims description 27
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
- 241000607479 Yersinia pestis Species 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 18
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 18
- 125000004414 alkyl thio group Chemical group 0.000 claims description 18
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 18
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 18
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 239000002917 insecticide Substances 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 12
- 241000254173 Coleoptera Species 0.000 claims description 8
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 239000000575 pesticide Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- -1 ters Chemical class 0.000 description 19
- 239000000203 mixture Substances 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000012442 inert solvent Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001340 alkali metals Chemical group 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 235000013312 flour Nutrition 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 241000244206 Nematoda Species 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 5
- 230000000749 insecticidal effect Effects 0.000 description 5
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
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- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
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- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 4
- 150000007529 inorganic bases Chemical class 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- VSZYPVDJXWAGLA-DAFODLJHSA-N (2E)-2-hydrazinylideneacetic acid Chemical compound N\N=C\C(O)=O VSZYPVDJXWAGLA-DAFODLJHSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- XUJFOSLZQITUOI-UHFFFAOYSA-N 4-(trifluoromethoxy)aniline Chemical compound NC1=CC=C(OC(F)(F)F)C=C1 XUJFOSLZQITUOI-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 241000254171 Curculionidae Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241000257159 Musca domestica Species 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 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
- 239000004927 clay Substances 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- YCHFCKWRGIPCMO-UHFFFAOYSA-N 2-(phenylhydrazinylidene)acetic acid Chemical compound OC(=O)C=NNC1=CC=CC=C1 YCHFCKWRGIPCMO-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 241001177117 Lasioderma serricorne Species 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- 241000012186 Litura Species 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241000409991 Mythimna separata Species 0.000 description 2
- 241001477931 Mythimna unipuncta Species 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
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- 238000009835 boiling Methods 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
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- 150000004678 hydrides Chemical class 0.000 description 2
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- OKIUYHDAGXRDCH-UHFFFAOYSA-N n-phenyl-2-(trifluoromethoxy)acetamide Chemical compound FC(F)(F)OCC(=O)NC1=CC=CC=C1 OKIUYHDAGXRDCH-UHFFFAOYSA-N 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
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- 239000011591 potassium Substances 0.000 description 2
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- QWDBCIAVABMJPP-UHFFFAOYSA-N Diisopropyl phthalate Chemical compound CC(C)OC(=O)C1=CC=CC=C1C(=O)OC(C)C QWDBCIAVABMJPP-UHFFFAOYSA-N 0.000 description 1
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- 241000462639 Epilachna varivestis Species 0.000 description 1
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- 239000005977 Ethylene Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 241000721621 Myzus persicae Species 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- PQBAWAQIRZIWIV-UHFFFAOYSA-N N-methylpyridinium Chemical compound C[N+]1=CC=CC=C1 PQBAWAQIRZIWIV-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 240000002853 Nelumbo nucifera Species 0.000 description 1
- 235000006508 Nelumbo nucifera Nutrition 0.000 description 1
- 235000006510 Nelumbo pentapetala Nutrition 0.000 description 1
- 241001556089 Nilaparvata lugens Species 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 241001203898 Olethreutes Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
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- 241000255969 Pieris brassicae Species 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241000193943 Pratylenchus Species 0.000 description 1
- 241000283080 Proboscidea <mammal> Species 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 241001630079 Pseudaonidia duplex Species 0.000 description 1
- 241001446203 Pulvinaria aurantii Species 0.000 description 1
- 244000088415 Raphanus sativus Species 0.000 description 1
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
- 241000931987 Sesamia Species 0.000 description 1
- 241000009334 Singa Species 0.000 description 1
- 241000254152 Sitophilus oryzae Species 0.000 description 1
- 241000254154 Sitophilus zeamais Species 0.000 description 1
- 241000176086 Sogatella furcifera Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241000256248 Spodoptera Species 0.000 description 1
- 241001417773 Spulerina Species 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000255588 Tephritidae Species 0.000 description 1
- 241000546225 Tomicus Species 0.000 description 1
- 241000018135 Trialeurodes Species 0.000 description 1
- 241001267618 Tylenchulus Species 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 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
- RSESUCWJKLHXEZ-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=CC=CC(C(F)(F)F)=C1 RSESUCWJKLHXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000003973 alkyl amines Chemical group 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 235000021329 brown rice Nutrition 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000001999 effect on insects Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940096118 ella Drugs 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
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- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000010881 fly ash Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000011812 mixed powder Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003090 pesticide formulation Substances 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- MQHNKCZKNAJROC-UHFFFAOYSA-N phthalic acid dipropyl ester Natural products CCCOC(=O)C1=CC=CC=C1C(=O)OCCC MQHNKCZKNAJROC-UHFFFAOYSA-N 0.000 description 1
- 235000010204 pine bark Nutrition 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 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
- 239000000126 substance Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- OOLLAFOLCSJHRE-ZHAKMVSLSA-N ulipristal acetate Chemical compound C1=CC(N(C)C)=CC=C1[C@@H]1C2=C3CCC(=O)C=C3CC[C@H]2[C@H](CC[C@]2(OC(C)=O)C(C)=O)[C@]2(C)C1 OOLLAFOLCSJHRE-ZHAKMVSLSA-N 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- 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】本発明は一般式(I) (式中、R1、R2、R3及びR4はは同一又は異なっても良
く、水素原子又は低級アルキル基を示し、Xは同一又は
異なっても良く、ハロゲン原子、ニトロ基、低級アルキ
ル基、低級ハロアルキル基、低級アルコキシ基、低級ア
ルキルチオ基、低級アルキルスルフィニル基又は低級ア
ルキルスルホニル基を示し、Yは同一又は異なっても良
く、ハロゲン原子、シアノ基、ニトロ基、低級アルキル
基、低級ハロアルキル基、低級アルコキシ基、低級ハロ
アルコキシ基、低級アルキルチオ基、低級アルキルスル
フィニル基、低級アルキルスルホニル基、低級ハロアル
キルチオ基、低級ハロアルキルスルフィニル基、低級ハ
ロアルキルスルホニル基、低級アルキニル基又は低級ア
ルコキシカルボニル基を示し、Zは同一又は異なっても
良く、ハロゲン原子、ニトロ基、シアノ基、低級アルキ
ル基、低級ハロアルキル基、低級アルコキシ基、低級ハ
ロアルコキシ基、低級アルキルチオ基、低級ハロアルキ
ルチオ基、低級アルキルスルフィニル基、低級ハロアル
キルスルフィニル基、低級アルキルスルホニル基、低級
ハロアルキルスルホニル基、低級ハロアルキルスルホニ
ルオキシ基、低級アルキルカルボニル基又はフェノキシ
基を示し、l、m及びnは各々0〜5の整数を示す。)
で表されるヒドラゾン誘導体、その製造方法及び農園芸
用殺虫剤並びにその使用方法に関するものである。The present invention relates to a compound of the formula (I) (Wherein, R 1 , R 2 , R 3 and R 4 may be the same or different and each represents a hydrogen atom or a lower alkyl group; X may be the same or different; a halogen atom, a nitro group, a lower alkyl A lower haloalkyl group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfinyl group or a lower alkylsulfonyl group, Y may be the same or different, and a halogen atom, a cyano group, a nitro group, a lower alkyl group, a lower haloalkyl Group, lower alkoxy group, lower haloalkoxy group, lower alkylthio group, lower alkylsulfinyl group, lower alkylsulfonyl group, lower haloalkylthio group, lower haloalkylsulfinyl group, lower haloalkylsulfonyl group, lower alkynyl group or lower alkoxycarbonyl group , Z may be the same or different, and , Nitro group, cyano group, lower alkyl group, lower haloalkyl group, lower alkoxy group, lower haloalkoxy group, lower alkylthio group, lower haloalkylthio group, lower alkylsulfinyl group, lower haloalkylsulfinyl group, lower alkylsulfonyl group, lower haloalkyl It represents a sulfonyl group, a lower haloalkylsulfonyloxy group, a lower alkylcarbonyl group or a phenoxy group, and l, m and n each represent an integer of 0 to 5.)
The present invention relates to a hydrazone derivative represented by the formula:
【0002】[0002]
【従来の技術】特開昭48−91223号、特開昭54
−122261号、特開昭56−45452号、特開昭
63−93761号公報等にヒドラゾン類が殺虫剤、有
害生物防除剤として開示されている。2. Description of the Related Art JP-A-48-91223 and JP-A-54
Hydrazones are disclosed as insecticides and pesticides in JP-A-122261, JP-A-56-45452, JP-A-63-93761, and the like.
【発明が解決しようとする課題】本発明者等は新規な殺
虫剤を創出すべく鋭意研究を重ねた結果,一般式(I) で
表されるヒドラゾン誘導体が先行技術文献等に記載も示
唆もされておらず、文献未記載の新規化合物であり、且
つ低薬量で優れた殺虫効果を有することを見出し本発明
を完成させたものである.The inventors of the present invention have conducted intensive studies to create a novel insecticide. As a result, the hydrazone derivative represented by the general formula (I) has been described or suggested in the prior art literature or the like. The present invention has been found to be a novel compound which has not been described, and which has not been described in the literature, and has an excellent insecticidal effect at a low dose, and has completed the present invention.
【0003】[0003]
【課題を解決するための手段】本発明の一般式(I) で表
されるヒドラゾン誘導体の代表的な製造方法としては、
例えば下記に図示する製造方法により製造することがで
きる。 (式中、R1、R2、R3、R4、R5、X、Y、Z、l、m及び
nは前記に同じ。) 一般式(III) で表される化合物と一般式(II)で表される
アニリン類とを不活性溶媒の存在下、塩基及び又は縮合
剤の存在下又は不存在下に反応させるか、又は一般式(I
V)で表される化合物と一般式(V) で表されるハライド類
とを不活性溶媒及び塩基の存在下に反応させることによ
り一般式(I) で表されるヒドラゾン誘導体を製造するこ
とができる。Means for Solving the Problems A typical method for producing the hydrazone derivative represented by the general formula (I) of the present invention includes:
For example, it can be manufactured by the manufacturing method shown below. (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , X, Y, Z, 1, m and n are the same as described above.) The compound represented by the general formula (III) and the general formula (III) The aniline represented by the formula (II) is reacted in the presence of an inert solvent, in the presence or absence of a base and / or a condensing agent, or is reacted with the general formula (I
A hydrazone derivative represented by the general formula (I) can be produced by reacting a compound represented by the formula (V) with a halide represented by the general formula (V) in the presence of an inert solvent and a base. it can.
【0004】1.一般式(III) → 一般式(I) 本反応で使用できる不活性溶媒としては、本反応の進行
を著しく阻害しないものであれば良く、例えばジクロロ
メタン、クロロホルム、四塩化炭素等のハロゲン化炭化
水素類、ベンゼン、トルエン、キシレン等の芳香族炭化
水素類、アセトニトリル、ベンゾニトリル等のニトリル
類、メチルセロソルブ、ジエチルエ−テル等の鎖状エ−
テル類、ジオキサン、テトラヒドロフラン等の環状エ−
テル類、アセトン、メチルエチルケトン等のケトン類、
酢酸エチル等のエステル類、N,N−ジメチルホルムア
ミド(DMF)、ジメチルスルホキシド(DMSO)、
ピリジン等を例示することができ、これらの不活性溶媒
は単独で使用しても良く、混合して使用することもでき
る。本反応で使用する塩基としては有機塩基又は無機塩
基を使用することができ、無機塩基としては、例えばナ
トリウム、カリウム等のアルカリ金属原子、カルシウ
ム、マグネシウム等アルカリ土類金属原子の水酸化物又
は炭酸塩等、水素化ナトリウム等のアルカリ金属原子の
水素化物、有機塩基としてはトリエチルアミン、ピリジ
ン、N,N−ジメチルアニリン、2,6−ジメチルピリ
ジン、4−N,N−ジメチルアミノピリジン等を使用す
ることができ,その使用量は触媒量乃至一般式(III) で
表される化合物に対して等モル乃至過剰モルの範囲から
選択して使用することができる。[0004] 1. General formula (III) → General formula (I) As the inert solvent that can be used in this reaction, any solvent that does not significantly inhibit the progress of this reaction may be used.Examples include halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride. , Aromatic hydrocarbons such as benzene, toluene and xylene; nitriles such as acetonitrile and benzonitrile; and chain ethers such as methylcellosolve and diethyl ether.
Cyclic ethers such as ters, dioxane, tetrahydrofuran, etc.
Ketones such as ters, acetone, methyl ethyl ketone,
Esters such as ethyl acetate, N, N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO),
Pyridine and the like can be exemplified, and these inert solvents may be used alone or in combination. As the base used in this reaction, an organic base or an inorganic base can be used.Examples of the inorganic base include hydroxides or carbonates of alkali metal atoms such as sodium and potassium, and alkaline earth metal atoms such as calcium and magnesium. Salts, hydrides of alkali metal atoms such as sodium hydride, and organic bases such as triethylamine, pyridine, N, N-dimethylaniline, 2,6-dimethylpyridine, 4-N, N-dimethylaminopyridine and the like are used. The amount thereof can be selected from the range of the amount of the catalyst or from the equimolar amount to the excess molar amount with respect to the compound represented by the general formula (III).
【0005】縮合剤としては、例えばカルボジイミダゾ
−ル、ジシクロヘキシルカルボジイミド、ヨウ化2−ク
ロロ−1−メチルピリジニウム等を使用することがで
き、その使用量は一般式(III) で表される化合物に対し
て等モル乃至過剰モルの範囲から選択して使用すれば良
い。本反応は等モル反応であるので、各反応剤を等モル
使用すれば良いが、アニリン類を過剰に使用することも
できる。反応温度は室温乃至使用する不活性溶媒の沸点
域の範囲から適宜選択すれば良く、好ましくは加熱下に
行うのが良い。反応時間は反応量、反応温度等により一
定しないが、数分乃至48時間の範囲から選択すれば良
い。反応終了後、目的物を含む反応液から常法、例えば
溶媒留去、溶媒抽出等を行い、必要に応じて再結晶法、
カラムクロマトグラフィ−法等により精製することによ
り目的物を製造することができる。As the condensing agent, for example, carbodiimidazole, dicyclohexylcarbodiimide, 2-chloro-1-methylpyridinium iodide and the like can be used, the amount of which is represented by the general formula (III) May be used by selecting from a range of equimolar to excess molar. Since this reaction is an equimolar reaction, each reactant may be used in an equimolar amount, but an aniline may be used in excess. The reaction temperature may be appropriately selected from the range of room temperature to the boiling point range of the inert solvent to be used, and the reaction is preferably carried out under heating. The reaction time is not fixed depending on the reaction amount, the reaction temperature and the like, but may be selected from a range of several minutes to 48 hours. After completion of the reaction, the reaction solution containing the target substance is subjected to a conventional method, for example, solvent distillation, solvent extraction, and the like, and if necessary, a recrystallization method,
The target product can be produced by purification by column chromatography or the like.
【0006】2.一般式(IV) → 一般式(I) 一般式(IV)で表される化合物と一般式(V) で表されるハ
ライド類とを不活性溶媒及び塩基の存在下に反応させる
ことにより一般式(I) で表されるヒドラゾン誘導体を製
造することができる。本反応で使用できる不活性溶媒と
しては、本反応の進行を著しく阻害しないものであれば
良く、例えばメタノ−ル、エタノ−ル、プロパノ−ル等
のアルコ−ル類、ジクロロメタン、クロロホルム、四塩
化炭素等のハロゲン化炭化水素類、ベンゼン、トルエ
ン、キシレン等の芳香族炭化水素類、アセトニトリル、
ベンゾニトリル等のニトリル類、メチルセロソルブ、ジ
エチルエ−テル等の鎖状エ−テル類、ジオキサン、テト
ラヒドロフラン等の環状エ−テル類、アセトン等のケト
ン類、酢酸エチル等のエステル類、ジメチルホルムアミ
ド、ジメチルアセトアミド、ジメチルスルホキシド、水
等を例示することができ、これらの不活性溶媒は単独で
使用しても良く、混合して使用することもできる。本反
応で使用する塩基としては有機塩基又は無機塩基を使用
することができ、無機塩基としては、例えばナトリウ
ム、カリウム等のアルカリ金属原子、カルシウム、マグ
ネシウム等アルカリ土類金属原子の水酸化物又は炭酸塩
等、水素化ナトリウム等のアルカリ金属原子の水素化
物、有機塩基としてはナトリウムメトキサイド、カリウ
ムt-ブトキサイド等のアルカリ金属原子のアルコラ−ト
類、ナトリウムアミン等のアルカリ金属原子のアミノ化
物、トリエチルアミン等の三級アルキルアミン類、ピリ
ジン、4−N,N−ジメチルアミノピリジン等を使用す
ることができる。[0006] 2. General formula (IV) → General formula (I) The compound represented by general formula (IV) is reacted with a halide represented by general formula (V) in the presence of an inert solvent and a base to form a compound represented by general formula (IV). The hydrazone derivative represented by (I) can be produced. The inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit the progress of this reaction, and examples thereof include alcohols such as methanol, ethanol, and propanol, dichloromethane, chloroform, and tetrachloride. Halogenated hydrocarbons such as carbon, benzene, toluene, aromatic hydrocarbons such as xylene, acetonitrile,
Nitriles such as benzonitrile, chain ethers such as methyl cellosolve and diethyl ether, cyclic ethers such as dioxane and tetrahydrofuran, ketones such as acetone, esters such as ethyl acetate, dimethylformamide, dimethyl Acetamide, dimethyl sulfoxide, water and the like can be exemplified. These inert solvents may be used alone or in combination. As the base used in this reaction, an organic base or an inorganic base can be used.Examples of the inorganic base include hydroxides or carbonates of alkali metal atoms such as sodium and potassium, and alkaline earth metal atoms such as calcium and magnesium. Salts, hydrides of alkali metal atoms such as sodium hydride, organic bases include sodium methoxide, alkali metal alcoholates such as potassium t-butoxide, aluminides of alkali metal atoms such as sodium amine, triethylamine And the like. Tertiary alkylamines such as pyridine, 4-N, N-dimethylaminopyridine and the like can be used.
【0007】塩基の使用量は一般式(IV)で表される化合
物に対して等モル乃至過剰モルの範囲から選択して使用
すれば良い。本反応は等モル反応であるので各反応剤を
等モル使用すれば良いが、一般式(V) で表されるハライ
ド類を過剰に使用することもできる。反応温度は室温乃
至使用する不活性溶媒の沸点域の範囲から適宜選択すれ
ば良い。反応時間は反応量、反応温度等により一定しな
いが、数分乃至48時間の範囲から選択すれば良い。反
応終了後、前記の反応と同様にすることにより目的物を
製造することができる。本発明の一般式(I) で表される
ヒドラゾン誘導体を製造する際の原料化合物である一般
式(III) で表される化合物は特開昭62- 223169号、同64
-70462号公報、J.Org.Chem.,417(1941) 、Ber. 56B, 10
60-1065(1923) 等に記載の方法により製造することがで
きる。又一般式(IV)で表される化合物は Collection Cz
ech. Chem. Communs.,25,2651-2667(1960)に記載の方法
により製造することができる。以下に本発明の一般式
(I) を第1表に例示するが、本発明はこれらの化合物に
限定されるものではない。The amount of the base used may be selected from the range of equimolar to excess molar with respect to the compound represented by the general formula (IV). Since this reaction is an equimolar reaction, each reactant may be used in an equimolar amount, but the halides represented by the general formula (V) may be used in excess. The reaction temperature may be appropriately selected from the range from room temperature to the boiling point range of the inert solvent used. The reaction time is not fixed depending on the reaction amount, the reaction temperature and the like, but may be selected from a range of several minutes to 48 hours. After completion of the reaction, the target product can be produced in the same manner as in the above reaction. The compound represented by the general formula (III), which is a raw material compound for producing the hydrazone derivative represented by the general formula (I) of the present invention, is disclosed in JP-A-62-2223169 and JP-A-64-223169.
-70462, J. Org. Chem., 417 (1941), Ber. 56B, 10
60-1065 (1923). The compound represented by the general formula (IV) is Collection Cz
ech. Chem. Communs., 25, 261-2667 (1960). The general formula of the present invention is shown below.
(I) is exemplified in Table 1, but the present invention is not limited to these compounds.
【0008】一般式(I) (以下余白)General formula (I) (Below)
【表1】 [Table 1]
【表2】 [Table 2]
【表3】 [Table 3]
【表4】 [Table 4]
【表5】 [Table 5]
【表6】 [Table 6]
【0009】第1表中、物性がペースト状物のNMRデ
−タを第2表に示す。 以下に本発明の代表的な実施例を示すが本発明はこれら
に限定されるものではない。In Table 1, NMR data of the paste-like material are shown in Table 2. Hereinafter, typical examples of the present invention will be described, but the present invention is not limited thereto.
【0010】実施例11−1 . 2−〔N−(4−シアノベンジル)−N−
(3−トリフルオロメチルフェニル)〕ヒドラゾノ酢酸
の製造 3−トリフルオロメチルフェニルヒドラジン13.46
g(76.5ミリモル)をトルエン100mlに溶解し、
トリエチルアミン8.12g(80.4ミリモル)及び
4−シアノベンジルブロミド14.99g(76.5ミ
リモル)を加え、3時間加熱下に反応を行った。反応終
了後、反応液を水洗(50ml×2)し有機層を濃縮し、
次いで濃縮物をエタノ−ル80mlに溶解し、氷冷下に4
0%グリオキシル酸水溶液11.51g(62.2ミリ
モル)を滴下し、室温下に2時間攪拌を行った。反応終
了後、目的物を含む反応溶液から溶媒を留去し、水50
mlを加え、酢酸エチル(100ml×2)で抽出し、抽出
液を無水硫酸ナトリウムで乾燥し、減圧下に濃縮して析
出した結晶をヘキサン−エ−テル混合液で洗浄し、1
3.02gの目的物を得た。 物性: m.p.220℃ 収率 60.2%Embodiment 1 1-1 . 2- [N- (4-cyanobenzyl) -N-
Production of (3-trifluoromethylphenyl)] hydrazonoacetic acid 13.46 3-trifluoromethylphenylhydrazine
g (76.5 mmol) in 100 ml of toluene,
8.12 g (80.4 mmol) of triethylamine and 14.99 g (76.5 mmol) of 4-cyanobenzyl bromide were added, and the reaction was carried out under heating for 3 hours. After completion of the reaction, the reaction solution was washed with water (50 ml × 2), and the organic layer was concentrated.
Then, the concentrate was dissolved in 80 ml of ethanol, and
11.51 g (62.2 mmol) of a 0% glyoxylic acid aqueous solution was added dropwise, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was distilled off from the reaction solution containing the target substance, and water 50
The mixture was extracted with ethyl acetate (100 ml × 2), the extract was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the precipitated crystals were washed with a hexane-ether mixed solution.
3.02 g of the desired product was obtained. Physical properties: mp 220 ° C Yield 60.2%
【0011】1−2. 2−〔N−(4−シアノベンジ
ル)−N−(3−トリフルオロメチルフェニル)〕ヒド
ラゾノ 4−クロロアセトアニリドの製造(化合物No.
39) 1−1で得られた2−〔N−(4−シアノベンジル)−
N−(3−トリフルオロメチルフェニル)〕ヒドラゾノ
酢酸0.59g(1.7ミリモル)を四塩化炭素7mlに
懸濁し、塩化チオニル0.40g(3.4ミリモル)を
加え、1.5時間加熱還流した。反応終了後、反応溶媒
を減圧下に留去して得られた酸クロリドを、4−クロロ
アニリン0.62g(1.7ミリモル)及びトリエチル
アミン0.37g(3.7ミリモル)をテトラヒドロフ
ラン10mlに溶解した溶液に加え、室温下で1時間攪拌
を行った。反応終了後、反応液に水10mlを加えて目的
物を酢酸エチル(100ml×2)で抽出し、抽出液を無
水硫酸ナトリウムで乾燥し、減圧下に濃縮した。得られ
た残渣をシリカゲルカラムクロマトグラフィ−(ヘキサ
ン−酢酸エチル)で精製し、0.51gの目的物を得
た。 物性 m.p.164−165℃ 収率 65.0%. 1-2 . Production of 2- [N- (4-cyanobenzyl) -N- (3-trifluoromethylphenyl)] hydrazono 4-chloroacetanilide (Compound No.
39) 2- [N- (4-cyanobenzyl)-obtained in 1-1.
[N- (3-trifluoromethylphenyl)] hydrazonoacetic acid (0.59 g, 1.7 mmol) was suspended in 7 ml of carbon tetrachloride, 0.40 g (3.4 mmol) of thionyl chloride was added, and the mixture was heated for 1.5 hours. Refluxed. After completion of the reaction, the reaction solvent was distilled off under reduced pressure, and the acid chloride obtained was dissolved in 10 ml of tetrahydrofuran with 0.62 g (1.7 mmol) of 4-chloroaniline and 0.37 g (3.7 mmol) of triethylamine. The mixture was stirred at room temperature for 1 hour. After completion of the reaction, 10 ml of water was added to the reaction solution, and the desired product was extracted with ethyl acetate (100 ml × 2). The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 0.51 g of the desired product. Physical properties mp 164-165 ° C Yield 65.0%.
【0012】実施例2 2−〔N−(3−クロロフェニ
ル)−N−(4−シアノベンジル)〕ヒドラゾノ 4−
トリフルオロメトキシアセトアニリドの製造(化合物N
o. 22) 1−1と同様にして製造した2−〔N−(3−クロロフ
ェニル)−N−(4−シアノベンジル)〕ヒドラゾノ酢
酸1.50g(4.8ミリモル)、ヨウ化2−クロロ−
1−メチルピリジニウム1.34g(5.3ミリモ
ル)、4−トリフルオロメトキシアニリン0.85g
(4.8ミリモル)をピリジン20mlに溶解し3時間加
熱還流した。反応終了後、溶媒を留去し、水30mlを加
えて目的物を酢酸エチル(50ml×2)で抽出し、抽出
液を無水硫酸ナトリウムで乾燥し、減圧下に濃縮した。
得られた残渣をシリカゲルカラムクロマトグラフィ−
(ヘキサン−酢酸エチル)で精製して1.64gの目的
物を得た。 物性 m.p.160.5−162.0℃ 収率 72.
3%.Example 2 2- [N- (3-chlorophenyl) -N- (4-cyanobenzyl)] hydrazono 4-
Production of trifluoromethoxyacetanilide (Compound N
o. 22) 1.50 g (4.8 mmol) of 2- [N- (3-chlorophenyl) -N- (4-cyanobenzyl)] hydrazonoacetic acid prepared in the same manner as in 1-1, 2-chloro-iodide
1.34 g (5.3 mmol) of 1-methylpyridinium, 0.85 g of 4-trifluoromethoxyaniline
(4.8 mmol) was dissolved in 20 ml of pyridine and heated under reflux for 3 hours. After completion of the reaction, the solvent was distilled off, 30 ml of water was added, and the desired product was extracted with ethyl acetate (50 ml × 2). The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure.
The obtained residue is subjected to silica gel column chromatography.
(Hexane-ethyl acetate) to give 1.64 g of the desired product. Physical properties mp 160.5-162.0 ° C Yield 72.
3%.
【0013】実施例3 2−〔N−(4−クロロフェニ
ル)−N−(4−ニトロベンジル)〕ヒドラゾノ 4−
トリフルオロメトキシアセトアニリドの製造(化合物N
o. 28) 1−1と同様にして製造した2−〔N−(4−クロロフ
ェニル)−N−(4−ニトロベンジル)〕ヒドラゾノ酢
酸1.30g(3.9ミリモル)及びカルボニルジイミ
ダゾ−ル0.63g(3.9ミリモル)をテトラヒドロ
フラン10mlに溶解し、室温下に5時間攪拌を行った。
反応終了後、水30mlを加えて酢酸エチル(50ml×
2)で抽出し、抽出液を無水硫酸ナトリウムで乾燥し、
減圧下に濃縮して得られた残渣をピリジン20mlに溶解
し、4−トリフルオロメトキシアニリン0.69g
(3.9ミリモル)及び4−ジメチルアミノピリジン
0.10g(0.8ミリモル)を加えて12時間加熱還
流下に攪拌を行った。反応終了後,溶媒を留去して水3
0mlを加え,目的物を酢酸エチル(50ml×2)で抽出
し、抽出液を無水硫酸ナトリウムで乾燥し、減圧下に濃
縮して得られた残渣をシリカゲルカラムクロマトグラフ
ィ−(ヘキサン−酢酸エチル)で精製し0.95gの目
的物を得た。 物性 m.p.111.0−115.1℃ 収率 49.
5%.Example 3 2- [N- (4-chlorophenyl) -N- (4-nitrobenzyl)] hydrazono 4-
Production of trifluoromethoxyacetanilide (Compound N
o. 28) 1.30 g (3.9 mmol) of 2- [N- (4-chlorophenyl) -N- (4-nitrobenzyl)] hydrazonoacetic acid and 0.63 g of carbonyldiimidazole prepared in the same manner as in 1-1. (3.9 mmol) was dissolved in 10 ml of tetrahydrofuran and stirred at room temperature for 5 hours.
After completion of the reaction, 30 ml of water was added and ethyl acetate (50 ml ×
Extract in 2), dry the extract with anhydrous sodium sulfate,
The residue obtained by concentration under reduced pressure was dissolved in 20 ml of pyridine, and 0.69 g of 4-trifluoromethoxyaniline was dissolved.
(3.9 mmol) and 0.10 g (0.8 mmol) of 4-dimethylaminopyridine were added, and the mixture was stirred under heating and reflux for 12 hours. After completion of the reaction, the solvent is distilled off and water 3
0 ml was added, the desired product was extracted with ethyl acetate (50 ml × 2), the extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue obtained was subjected to silica gel column chromatography (hexane-ethyl acetate). Purification yielded 0.95 g of the desired product. Physical properties mp 111.0-115.1 ° C. Yield 49.
5%.
【0014】実施例44−1 . 2−フェニルヒドラゾノ 4−トリフルオロ
メトキシアセトアニリドの製造 フェニルヒドラジン30.24g(0.28モル)をエ
タノ−ル200mlに溶解し、氷冷下に40%グリオキシ
ル酸水溶液51.80g(0.28モル)を滴下し、室
温下に2時間攪拌した。反応終了後、溶媒を減圧下に留
去して析出した結晶をヘキサン−エ−テル混合液で洗浄
することにより、フェニルヒドラゾノ酢酸20.2gを
得た(収率 43.9%)。得られたフェニルヒドラゾ
ノ酢酸7.81g(47.6ミリモル)及びトリエチル
アミン10.58g(104.7ミリモル)をジクロロ
メタン30mlに溶解した溶液を、ヨウ化2−クロロ−1
−メチルピリジニウム12.17g(47.6ミリモ
ル)及び4−トリフルオロメトキシアニリン8.43g
(47.6ミリモル)をジクロロメタン100mlに溶解
した溶液に滴下し、室温下に5時間攪拌を行った。反応
終了後、溶媒を留去して水50mlを加え、目的物を酢酸
エチル(100ml×2)で抽出し、抽出液を無水硫酸ナ
トリウムで乾燥し、減圧下に濃縮し、得られた残渣をシ
リカゲルカラムクロマトグラフィ−(ヘキサン−酢酸エ
チル)で精製して7.62gの目的物を得た。 物性 m.p.151.2−154.3℃ 収率 49.
6%.Embodiment 4 4-1 . Production of 2-phenylhydrazono 4-trifluoromethoxyacetanilide 30.24 g (0.28 mol) of phenylhydrazine was dissolved in 200 ml of ethanol, 51.80 g (0.28 mol) of a 40% aqueous glyoxylic acid solution was added dropwise under ice cooling, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the precipitated crystals were washed with a hexane-ether mixed solution to obtain 20.2 g of phenylhydrazonoacetic acid (43.9% yield). A solution of 7.81 g (47.6 mmol) of the obtained phenylhydrazonoacetic acid and 10.58 g (104.7 mmol) of triethylamine in 30 ml of dichloromethane was added to 2-chloro-1 iodide.
12.17 g (47.6 mmol) of -methylpyridinium and 8.43 g of 4-trifluoromethoxyaniline
(47.6 mmol) was added dropwise to a solution of 100 ml of dichloromethane and stirred at room temperature for 5 hours. After completion of the reaction, the solvent was distilled off, 50 ml of water was added, the desired product was extracted with ethyl acetate (100 ml × 2), the extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Purification by silica gel column chromatography (hexane-ethyl acetate) gave 7.62 g of the desired product. Physical properties mp 151.2-154.3 ° C Yield 49.
6%.
【0015】4−2. tert−ブチル 4−〔2−
(4−トリフルオロメトキシフェニルカルバモイルメチ
ル−N−フェニルヒドラゾノ−N−メチル)安息香酸の
製造(化合物No. 11) 4−1で得られたフェニルヒドラゾノ 4−トリフルオ
ロメトキシアセトアニリド0.71g(2.2ミリモ
ル)をジメチルホルムアミド20mlに溶解し、氷冷下に
カリウムtert- ブトキシド0.27g(2.4ミリモ
ル)及びtert- ブチル 4−クロロメチル安息香酸0.
54gを加え、室温下に3時間反応を行った。反応終了
後、氷水50mlを加えて目的物を酢酸エチル(100ml
×2)で抽出し、抽出液を無水硫酸ナトリウムで乾燥
し、減圧下に濃縮して得られた残渣をシリカゲルカラム
クロマトグラフィ−(ヘキサン−酢酸エチル)で精製
し、0.70gの目的物を得た。 物性 m.p.142.2−143.7℃ 収率 70.
0%. 4-2 . tert-butyl 4- [2-
Production of (4-trifluoromethoxyphenylcarbamoylmethyl-N-phenylhydrazono-N-methyl) benzoic acid (Compound No. 11) 0.71 g (2.2 mmol) of phenylhydrazono 4-trifluoromethoxyacetanilide obtained in 4-1 was dissolved in 20 ml of dimethylformamide, and 0.27 g (2.4 mmol) of potassium tert-butoxide was cooled with ice. And tert-butyl 4-chloromethylbenzoic acid.
54 g was added, and the reaction was carried out at room temperature for 3 hours. After the completion of the reaction, 50 ml of ice water was added, and the desired product was treated with ethyl acetate (100 ml).
× 2), the extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 0.70 g of the desired product. Was. Physical properties mp 142.2-143.7 ° C Yield 70.
0%.
【0016】本発明の一般式(I) で表されるヒドラゾン
誘導体を有効成分とする農園芸用殺虫剤は水稲、野菜、
果樹、その他の作物及び花卉等を加害する各種農林、園
芸、貯穀害虫や衛生害虫或いは線虫等の害虫防除にに適
しており、例えばリンゴコカクモンハマキ(adoxophyes
orana fasciata )、チャノコカクモンハマキ(Ado-xo
phyes sp. )、リンゴコシンクイ(Grapholita inopina
ta)、ナシヒメシンクイガ(Grapholita mlesta )、マ
メシンクイガ(Leguminivora glycinivorella)、クワ
ハマキ(Olethreutes mori)、チャノホソガ(Caloptil
ia thevivora)、リンゴホソガ(Caloptilia zachrysa
)、キンモンホソガ(Phyllonorycterringoniella
)、ナシホソガ(Spulerina astaurota )、モンシロ
チョウ(Pie-rs rapae crucivora )、オオタバコガ類
(Heliothis sp. )、コドリンガ(L-aspeyresia pomon
ella)、コナガ(Plutella xylostella )、リンゴヒメ
シンクイ(Argyresthia conjugella)、モモシンクイガ
(Carposina niponensis)、ニカメイガ(Chilo suppre
ssalis)、コブノメイガ(Cnaphalocrocis medinali
s)、チャマダラメイガ(Ephestia elutella )、クワ
ノメイガ(Glyphodes pyloa-lis )、サンカメイガ(Sc
irpophaga incertulas)、イチモンジセセリ(Parna-ra
guttata)、アワヨトウ(Pseudaletia separata)、イ
ネヨトウ(Sesamia i-nferens )、ハスモンヨトウ(Sp
odoptera litura )、シロイチモンジヨトウ(Spodopte
ra exigua )等の鱗翅目害虫、フタテンヨコバイ(Macr
osteles fasci-frons )、ツマグロヨコバイ(Nephotet
tix cincticeps)、トビイロウンカ(N-ilaparvata lug
ens )、セジロウンカ(Sogatella furcifera )、ミカ
ンキジラミ(Diaphorina citri)、ブドウコナジラミ
(Aleurolobus taonabae)、タバココナジラミ(Bemisi
a tabaci)、オンシツコナジラミ(Trialeurodes vapor
ari-orum)、ニセダイコンアブラムシ(Lipaphis erysi
mi)、モモアカアブラムシ(Myzus persicae)、ツノロ
ウムシ(Ceroplastes ceriferus )、ミカンワタカイガ
ラムシ(Pulvinaria aurantii )、ミカンマルカイガラ
ムシ(Pseudaonidiaduplex)、ナシマルカイガラムシ
(Comstockaspis perniciosa)、ヤノネカイガラムシ
(Unaspis yanonensis )等の半翅目害虫、ネグサレセ
ンチュウ(Praty-lenchus sp. )、ヒメコガネ(Anomal
a rufocuprea )、マメコガネ(Popilliajaponica
)、タバコシバンムシ(Lasioderma serricorne )、
ヒラタキクイムシ(Lyctus brunneus )、ニジュウヤホ
シテントウ(Epilachna vigintioctopu-nctata)、アズ
キゾウムシ(Callosobruchus chinensis)、ヤサイゾウ
ムシ(L-istroderes costirostris )、コクゾウムシ
(Sitophilus zeamais)、ワタミゾウムシ(Anthonomus
grandis grandis)、イネミズゾウムシ(Lissorhoptru
s o-ryzophilus)、ウリハムシ(Aulacophora femorali
s )、イネドロオイムシ(O-ulema oryzae)、キスジノ
ミハムシ(Phyllotreta striolata )、コクゾウムシ
(Sitophilus zeamais)、マツノキクイムシ(Tomicus
piniperda)、コロラドポテトビ−トル(Leptinotarsa
decemlineata )、メキシカンビ−ンビ−トル(Epilac
hna varivestis)、コ−ンル−トワ−ム類(Diabrotica
sp.)、等の甲虫目害虫、ウリミバエ(Dacus(Zeugodac
us) cucurbitae)、ミカンコミバエ(Dac-us(Bactrocer
a) dorsalis )、イネハモグリバエ(Agromyza oryzae
)、タマネギバエ(Delia antiqua )、タネバエ(Del
ia platura )、ダイズサヤタマバエ(Asphondylia sp.
)、イエバエ(Musca domestica )、アカイエカ(Cul
ex p-ipiens pipiens )等の双翅目害虫、ミナミネグ
サレセンチュウ(Pratylenchu-s coffeae )、ジャガイ
モシストセンチュウ(Globodera rostochiensis )、ネ
コブセンチュウ(Meloidogyne sp. )、ミカンネセンチ
ュウ(Tylenchulus sem-ipenetrans)、ニセネグサレセ
ンチュウ(Aphelenchus avenae)、ハガレセンチュウ
(Aphelenchoides ritzemabosi)等のハリセンチュウ目
害虫等に対しても殺虫効果を有し、特に鱗翅目、甲虫目
等の害虫に対しては顕著な効果を有するものである。
尚、学名等は農林有害動物・昆虫名鑑1987年版(日本応
用動物昆虫学会編)による。The agricultural and horticultural insecticides containing the hydrazone derivative represented by the general formula (I) of the present invention as an active ingredient include rice, vegetables,
It is suitable for pest control such as various agriculture and forestry, horticulture, storage pests, sanitary pests, nematodes and the like which inflict fruit trees, other crops and flowers. For example, adoxophyes
orana fasciata)
phyes sp.), apple squirrel (Grapholita inopina)
ta), Nashihime Singa (Grapholita mlesta), Mameshin Singing (Leguminivora glycinivorella), Kuwamaki (Olethreutes mori), Canohosoga (Caloptil)
ia thevivora), apple hosoga (Caloptilia zachrysa)
), Kinmonhosoga (Phyllonorycterringoniella)
), Pear squirrel (Spulerina astaurota), white butterfly (Pie-rs rapae crucivora), giant tobacco (Heliothis sp.), Codling moth (L-aspeyresia pomon)
ella), diamondback moth (Plutella xylostella), apple squirrel (Argyresthia conjugella), peach squirrel (Carposina niponensis), squid (Chilo suppre)
ssalis, Coleoptera (Cnaphalocrocis medinali)
s), Chamodara moth (Ephestia elutella), Kuwanomeiga (Glyphodes pyloa-lis), Sankameiga (Sc)
irpophaga incertulas)
guttata), armyworm (Pseudaletia separata), rice armyworm (Sesamia i-nferens), lotus armyworm (Sp
Odoptera litura, Spodoptera litura (Spodopte)
ra exigua) and other lepidopteran pests, leafhopper leafhopper (Macr
osteles fasci-frons), leafhopper (Nephotet)
tix cincticeps), brown planthopper (N-ilaparvata lug)
ens), white-fed groundhopper (Sogatella furcifera), citrus whitefly (Diaphorina citri), grape whitefly (Aleurolobus taonabae), and tobacco whitefly (Bemisi)
a tabaci), Whiteflies (Trialeurodes vapor)
ari-orum), radish aphid (Lipaphis erysi)
mi), peach aphid (Myzus persicae), horned beetle (Ceroplastes ceriferus), citrus stag beetle (Pulvinaria aurantii), citrus red stalk (Pseudaonidiaduplex), pear stalk (Comstockaspis perniciosa), etc. Pterodactyl pests, Praty-lenchus sp.
a rufocuprea), Bean beetle (Popilliajaponica)
), Tobacco beetle (Lasioderma serricorne),
Flying bark beetle (Lyctus brunneus), Japanese beetle beetle (Epilachna vigintioctopu-nctata), adzuki beetle (Callosobruchus chinensis), beetle weevil (L-istroderes costirostris), weevil (Sitophilus zeomais)
grandis grandis), rice weevil (Lissorhoptru)
s o-ryzophilus, cricket beetle (Aulacophora femorali)
s), rice beetle (O-ulema oryzae), flea beetle (Phyllotreta striolata), weevil (Sitophilus zeamais), pine bark beetle (Tomicus)
piniperda, Colorado potatoes (Leptinotarsa)
decemlineata), Mexican beans (Epilac
hna varivestis), corn worms (Diabrotica)
sp.), beetles such as Coleoptera, sea flies (Dacus (Zeugodac
us) cucurbitae), Citrus fruit fly (Dac-us (Bactrocer)
a) dorsalis), rice leafhopper (Agromyza oryzae)
), Onion flies (Delia antiqua), flies (Del)
ia platura), soybean flies (Asphondylia sp.)
), Housefly (Musca domestica), Musca domestica (Cul)
ex p-ipiens pipiens), dipteran pests, Pratylenchu-s coffeae, potato cyst nematodes (Globodera rostochiensis), root-knot nematodes (Meloidogyne sp.), tangerine nematodes (Tylenchulus sem-ene) It also has an insecticidal effect against the nematodes of the order Nematodes (Aphelenchus avenae) and the nematodes (Aphelenchoides ritzemabosi), and particularly has a remarkable effect on insects such as Lepidoptera and Coleoptera. It is.
The scientific names are based on the 1987 Agricultural and Forestry Pests and Insects Directory (edited by the Japan Society of Applied Animal Entomology).
【0017】本発明の農園芸用殺虫剤は水田、果樹、野
菜、その他の作物及び花卉等を加害する前記害虫あるい
は衛生害虫に対して顕著な殺虫効果を有するものである
ので、害虫類の発生が予測される時期に合わせて、害虫
類の発生前又は発生が確認された時点で水田、果樹、野
菜、その他の作物、花卉等の水田水、茎葉又は土壌等及
び衛生害虫にあっては人畜に加害する上記害虫の発生若
しくは発生が予測される家屋内、家屋周辺の溝等に処理
することにより本発明の殺虫剤の所期の効果が奏せられ
るものである。しかし、本発明はこれらの態様のみに限
定されるものではない。本発明の一般式(I) で表される
ヒドラゾン誘導体を農園芸用殺虫剤として使用する場
合、農薬製剤上の常法に従い、使用上都合の良い形状に
製剤して使用するのが一般的である。即ち、本発明の一
般式(I) で表されるヒドラゾン誘導体は、これらを適当
な不活性担体に、又は必要に応じて補助剤と一緒に、適
当な割合に配合して溶解、分離、懸濁、混合、含浸、吸
着若しくは付着させ、適宜の剤形、例えば懸濁剤、乳
剤、液剤、水和剤、粒剤、粉剤、錠剤等に製剤して使用
すれば良い。本発明で使用できる不活性担体としては固
体又は液体の何れであっても良く、固体の担体になりう
る材料としては、例えばダイズ粉、穀物粉、木粉、樹皮
粉、鋸粉、タバコ茎粉、クルミ殻粉、ふすま、繊維素粉
末、植物エキス抽出後の残渣、粉砕合成樹脂等の合成重
合体、粘土類(例えばカオリン、ベントナイト、酸性白
土等)、タルク類(例えばタルク、ピロフィライド
等)、シリカ類(例えば珪藻土、珪砂、雲母、ホワイト
カ−ボン〔含水微粉珪素、含水珪酸ともいわれる合成高
分散珪酸で、製品により珪酸カルシウムを主成分として
含むものもある。〕)、活性炭、イオウ粉末、軽石、焼
成珪藻土、レンガ粉砕物、フライアッシュ、砂、炭酸カ
ルシウム、燐酸カルシウム等の無機鉱物性粉末、硫安、
燐安、硝安、尿素、塩安等の化学肥料、堆肥等を挙げる
ことができ、これらは単独で若しくは二種以上の混合物
の形で使用される。The agricultural and horticultural insecticide of the present invention has a remarkable insecticidal effect on the above-mentioned pests or sanitary pests that infect paddy fields, fruit trees, vegetables, other crops, flowers and the like. Before and after the occurrence of the pests is confirmed, the paddy fields, fruit trees, vegetables, other crops, paddy water such as flowers, foliage or soil, etc. The intended effect of the insecticide of the present invention can be obtained by treating the inside of a house or a ditch around a house where the occurrence of the above-mentioned pests or the occurrence of the above-mentioned pests is predicted. However, the present invention is not limited to only these embodiments. When the hydrazone derivative represented by the general formula (I) of the present invention is used as an agricultural and horticultural insecticide, it is generally used by formulating it into a convenient form according to a conventional method for pesticide formulation. is there. That is, the hydrazone derivatives of the present invention represented by the general formula (I) are dissolved, separated, suspended in a suitable inert carrier or, if necessary, together with an auxiliary in an appropriate ratio. It may be turbid, mixed, impregnated, adsorbed or adhered and formulated into an appropriate dosage form, for example, a suspension, emulsion, liquid, wettable powder, granule, powder, tablet or the like. The inert carrier that can be used in the present invention may be either solid or liquid. Examples of the material that can be a solid carrier include soybean flour, cereal flour, wood flour, bark flour, saw flour, and tobacco stem flour. , Walnut shell powder, bran, cellulose powder, residue after extraction of plant extract, synthetic polymers such as pulverized synthetic resins, clays (eg, kaolin, bentonite, acid clay), talcs (eg, talc, pyrophyllide, etc.), Silica (for example, diatomaceous earth, silica sand, mica, white carbon [a synthetic high-dispersion silicic acid which is also called hydrous finely divided silicon or hydrous silicic acid, and which contains calcium silicate as a main component depending on the product]), activated carbon, sulfur powder, Inorganic mineral powders such as pumice, calcined diatomaceous earth, crushed brick, fly ash, sand, calcium carbonate, calcium phosphate, ammonium sulfate,
Examples include chemical fertilizers such as phosphorous, nitrate, urea, and salt, and composts, and these are used alone or in the form of a mixture of two or more.
【0018】液体の担体になりうる材料としては、それ
自体溶媒能を有するものの他、溶媒能を有さずとも補助
剤の助けにより有効成分化合物を分散させうることとな
るものから選択され、例えば代表例として次に挙げる担
体を例示できるが、これらは単独で若しくは2種以上の
混合物の形で使用され、例えば水、アルコ−ル類(例え
ばメタノ−ル、エタノ−ル、イソプロパノ−ル、ブタノ
−ル、エチレングリコ−ル等)、ケトン類(例えばアセ
トン、メチルエチルケトン、メチルイソブチルケトン、
ジイソブチルケトン、シクロヘキサノン等)、エ−テル
類(例えばエチルエ−テル、ジオキサン、セロソルブ、
ジプロピルエ−テル、テトラヒドロフラン等)、脂肪族
炭化水素類(例えばケロシン、鉱油等)、芳香族炭化水
素類(例えばベンゼン、トルエン、キシレン、ソルベン
トナフサ、アルキルナフタレン等)、ハロゲン化炭化水
素類(例えばジクロロエタン、クロロホルム、四塩化炭
素、塩素化ベンゼン等)、エステル類(例えば酢酸エチ
ル、ジイソプピルフタレ−ト、ジブチルフタレ−ト、ジ
オクルフタレ−ト等)、アミド類(例えばジメチルホル
ムアミド、ジエチルホルムアミド、ジメチルアセトアミ
ド等)、ニトリル類(例えばアセトニトリル等)、ジメ
チルスルホキシド類等を挙げることができる。他の補助
剤としては次に例示する代表的な補助剤をあげることが
でき、これらの補助剤は目的に応じて使用され、単独
で、ある場合は二種以上の補助剤を併用し、又ある場合
には全く補助剤を使用しないことも可能である。The material which can be a liquid carrier is selected from those having a solvent function per se, and those capable of dispersing the active ingredient compound with the aid of an auxiliary even without the solvent function. The following carriers can be exemplified as typical examples. These can be used alone or in the form of a mixture of two or more. Examples thereof include water, alcohols (eg, methanol, ethanol, isopropanol, butanol). , Ethylene glycol and the like), ketones (for example, acetone, methyl ethyl ketone, methyl isobutyl ketone,
Diisobutyl ketone, cyclohexanone, etc.), ethers (eg, ethyl ether, dioxane, cellosolve,
Dipropyl ether, tetrahydrofuran, etc.), aliphatic hydrocarbons (eg, kerosene, mineral oil, etc.), aromatic hydrocarbons (eg, benzene, toluene, xylene, solvent naphtha, alkylnaphthalene, etc.), halogenated hydrocarbons (eg, dichloroethane) , Chloroform, carbon tetrachloride, chlorinated benzene, etc.), esters (eg, ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctophthalate), amides (eg, dimethylformamide, diethylformamide, dimethylacetamide) Etc.), nitriles (eg, acetonitrile, etc.), dimethyl sulfoxides and the like. Examples of the other adjuvants include the following representative adjuvants. These adjuvants are used according to the purpose, and may be used alone or in combination of two or more kinds. In some cases, it is possible to use no auxiliaries at all.
【0019】有効成分化合物の乳化、分散、可溶化及び
/又は湿潤の目的のために界面活性剤が使用され、例え
ばポリオキシエチレンアルキルエ−テル、ポリオキシエ
チレンアルキルアリ−ルエ−テル、ポリオキシエチレン
高級脂肪酸エステル、ポリオキシエチレン樹脂酸エステ
ル、ポリオキシエチレンソルビタンモノラウレ−ト、ポ
リオキシエチレンソルビタンモノオレエ−ト、アルキル
アリ−ルスルホン酸塩、ナフタレンスルホン酸縮合物、
リグニンスルホン酸塩、高級アルコ−ル硫酸エステル等
の界面活性剤を例示することができる。又、有効成分化
合物の分散安定化、粘着及び/又は結合の目的のため
に、次に例示する補助剤を使用することもでき、例えば
カゼイン、ゼラチン、澱粉、メチルセルロ−ス、カルボ
キシメチルセルロ−ス、アラビアゴム、ポリビニルアル
コ−ル、松根油、糠油、ベントナイト、リグニンスルホ
ン酸塩等の補助剤を使用することもできる。固体製品の
流動性改良のために次に挙げる補助剤を使用することも
でき、例えばワックス、ステアリン酸塩、燐酸アルキル
エステル等の補助剤を使用できる。懸濁性製品の解こう
剤として、例えばナフタレンスルホン酸縮合物、縮合燐
酸塩等の補助剤を使用することもできる。消泡剤として
は、例えばシリコ−ン油等の補助剤を使用することもで
きる。Surfactants are used for the purpose of emulsifying, dispersing, solubilizing and / or wetting the active ingredient compounds, such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene, and the like. Ethylene higher fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkyl aryl sulfonate, naphthalene sulfonic acid condensate,
Surfactants such as lignin sulfonate and higher alcohol sulfate can be exemplified. For the purpose of stabilizing the dispersion of the active ingredient compound, adhering and / or binding, the following auxiliaries can be used. For example, casein, gelatin, starch, methylcellulose, carboxymethylcellulose can be used. Auxiliaries such as gum arabic, polyvinyl alcohol, pine oil, bran oil, bentonite, and lignin sulfonate can also be used. The following auxiliaries can be used to improve the flowability of the solid product. For example, auxiliaries such as wax, stearate, alkyl phosphate and the like can be used. As peptizers for suspension products, auxiliary agents such as, for example, naphthalenesulfonic acid condensates, condensed phosphates and the like can also be used. As an antifoaming agent, for example, an auxiliary agent such as silicone oil can be used.
【0020】有効成分化合物の配合割合は必要に応じて
加減することができ、例えば粉剤或いは粒剤とする場合
は0.01〜50重量%、又乳剤或いは水和剤とする場
合も同様0.01〜50重量%が適当である。本発明の
一般式(I) で表されるヒドラゾン誘導体を有効成分とす
る農園芸用殺虫剤は、各種害虫を防除するために、その
まま、又は水等で適宜希釈し、若しくは懸濁させた形で
害虫防除に有効な量を当該害虫に、又は当該害虫の発生
若しくは成育が好ましくない場所に適用して使用すれば
よい。本発明の一般式(I) で表されるヒドラゾン誘導体
を有効成分とする農園芸用殺虫剤の使用量は種々の因
子、例えば目的、対象害虫、作物の生育状況、害虫の発
生傾向、天候、環境条件、剤型、施用方法、施用場所、
施用時期等により変動するが、有効成分化合物として1
0ア−ル当たり0.1g〜5Kgの範囲から目的に応じて
適宜選択すれば良い。本発明の一般式(I) で表されるヒ
ドラゾン誘導体を有効成分とする農園芸用殺虫剤を更に
防除対象害虫、防除適期の拡大のため、或いは薬量の低
減をはかる目的で他の殺虫剤又は殺菌剤と混合して使用
することも可能である。以下に本発明の代表的な処方例
及び試験例を示すが、本発明はこれらに限定されるもの
ではない。尚、処方例中、部とあるのは重量部を示す。The compounding ratio of the active ingredient compound can be adjusted according to need. For example, 0.01 to 50% by weight in the case of powder or granules, and 0.1% in the case of emulsion or wettable powder. A suitable amount is from 01 to 50% by weight. The agricultural and horticultural insecticide containing the hydrazone derivative represented by the general formula (I) of the present invention as an active ingredient is used as it is, or is appropriately diluted or suspended with water or the like in order to control various pests. An effective amount for controlling the pest may be applied to the pest or a place where the generation or growth of the pest is not preferable. The amount of the agricultural and horticultural insecticide containing the hydrazone derivative represented by the general formula (I) of the present invention as an active ingredient depends on various factors, for example, the purpose, the target pest, the growth status of the crop, the pest occurrence tendency, the weather, Environmental conditions, dosage forms, application methods, application locations,
Although it varies depending on the application time, etc., 1
It may be appropriately selected from the range of 0.1 g to 5 kg per 0 arc depending on the purpose. Agricultural and horticultural insecticides containing the hydrazone derivative represented by the general formula (I) of the present invention as an active ingredient are further used as pests to be controlled, other insecticides for the purpose of extending the suitable period of control, or for reducing the amount of drugs. Alternatively, it can be used in combination with a bactericide. Hereinafter, typical formulation examples and test examples of the present invention are shown, but the present invention is not limited thereto. In addition, in the formulation examples, "parts" indicates parts by weight.
【0021】処方例1 本発明化合物 50部 キシレン 40部 ポリオキシエチレンノニルフェニルエ−テルと アルキルベンゼンスルホン酸カルシウムとの混合物 10部 以上を均一に混合溶解して乳剤とする。 処方例2 本発明化合物 3部 クレ−粉末 82部 珪藻土粉末 15部 以上を均一に混合粉砕して粉剤とする。 処方例3 本発明化合物 5部 ベントナイトとクレ−の混合粉末 90部 リグニンスルホン酸カルシウム 5部 以上を均一に混合し、適量の水を加えて混練し、造粒、
乾燥して粒剤とする。 処方例4 本発明化合物 20部 カオリンと合成高分散珪酸 75部 ポリオキシエチレンノニルフェニルエ−テルとアル キルベンゼンスルホン酸カルシウムとの混合物 5部 以上を均一に混合粉砕して水和剤とする。Formulation Example 1 Compound of the present invention 50 parts Xylene 40 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts The above are uniformly mixed and dissolved to form an emulsion. Formulation Example 2 Compound of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above are uniformly mixed and pulverized to give a powder. Formulation Example 3 Compound of the present invention 5 parts Mixed powder of bentonite and clay 90 parts Calcium ligninsulfonate 5 parts The above components were uniformly mixed, kneaded by adding an appropriate amount of water, and granulated.
Dry to granules. Formulation Example 4 Compound of the present invention 20 parts Kaolin and synthetic highly dispersed silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts The above are uniformly mixed and pulverized to obtain a wettable powder.
【0022】試験例1 ハスモンヨトウ(Spodoptera
litura) に対する殺虫試験 本発明化合物を有効成分とする薬剤を500ppm に希釈
した薬液にキャベツ葉片(品種:四季穫)を約30秒間
浸漬した。風乾後に直径9cmのプラスチックシャ−レに
入れ、ハスモンヨトウ2令幼虫を接種した後、蓋をして
25℃恒温室に静置した。接種8日後に生死虫数を調査
し、下記の式により死虫率を算出し、下記の基準に従っ
て判定を行った。 1区10頭3連制Test Example 1 Spodoptera
Insecticidal test on litura ) Cabbage leaf pieces (variety: four seasons harvest) were immersed for about 30 seconds in a drug solution prepared by diluting a drug containing the compound of the present invention as an active ingredient to 500 ppm. After air-drying, it was placed in a plastic dish having a diameter of 9 cm, inoculated with the second instar larvae of Spodoptera litura, covered, and allowed to stand in a constant temperature room at 25 ° C. Eight days after the inoculation, the number of live and dead insects was investigated, the mortality was calculated by the following formula, and judgment was made according to the following criteria. 10 units in 1 ward, 3 consecutive
【式1】 判定基準. A・・・死虫率100% B・・・死虫率99%〜90% C・・・死虫率89%〜80% D・・・死虫率79%〜50% 結果を第3表に示す。(Equation 1) Judgment criteria. A: 100% mortality B: 99% to 90% mortality C: 89% to 80% mortality D: 79% to 50% mortality Table 3 Shown in
【0023】 [0023]
【0024】試験例2 コクゾウ(Sitophilus zeam
ais)成虫に対する殺虫試験 本発明化合物を有効成分とする薬剤を200ppm に希釈
した薬液に玄米を約30秒間浸漬した。風乾後に直径4
cmのガラスシャ−レに入れ、コクゾウ成虫を接種した
後、蓋をして25℃恒温室に静置した。接種8日後に生
死虫数を調査し、試験例1に従って死虫率を算出し、試
験例1の基準に従って判定を行った。1区10頭3連
制。結果を第4表に示す。Test Example 2 Sitophilus zeam
a ) Insecticidal test against adult insects Brown rice was immersed for about 30 seconds in a drug solution obtained by diluting a drug containing the compound of the present invention as an active ingredient to 200 ppm. Diameter 4 after air drying
After placing in a glass dish of cm and inoculating adult black elephants, it was covered and left to stand in a constant temperature room at 25 ° C. Eight days after the inoculation, the number of live and dead insects was examined, and the mortality was calculated according to Test Example 1. 10 units per ward in three wards. The results are shown in Table 4.
【0024】 [0024]
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 FI C07C 249/16 C07C 249/16 255/60 255/60 255/66 255/66 317/32 317/32 317/34 317/34 323/41 323/41 323/48 323/48 // A01N 25/04 101 A01N 25/04 101 (56)参考文献 特公 昭45−10519(JP,B1) (58)調査した分野(Int.Cl.6,DB名) C07C 251/74 A01N 37/18 A01N 37/34 A01N 41/04 A01N 41/10 C07C 249/16 C07C 255/60 C07C 255/66 C07C 317/32 C07C 317/34 C07C 323/41 C07C 323/48 CA(STN) REGISTRY(STN)──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. 6 Identification code FI C07C 249/16 C07C 249/16 255/60 255/60 255/66 255/66 317/32 317/32 317/34 317/34 323/41 323/41 323/48 323/48 // A01N 25/04 101 A01N 25/04 101 (56) References JP-B-45-10519 (JP, B1) (58) Fields surveyed (Int.Cl . 6, DB name) C07C 251/74 A01N 37/18 A01N 37/34 A01N 41/04 A01N 41/10 C07C 249/16 C07C 255/60 C07C 255/66 C07C 317/32 C07C 317/34 C07C 323/41 C07C 323/48 CA (STN) REGISTRY (STN)
Claims (15)
く、水素原子又は低級アルキル基を示し、Xは同一又は
異なっても良く、ハロゲン原子、ニトロ基、低級アルキ
ル基、低級ハロアルキル基、低級アルコキシ基、低級ア
ルキルチオ基、低級アルキルスルフィニル基又は低級ア
ルキルスルホニル基を示し、Yは同一又は異なっても良
く、ハロゲン原子、シアノ基、ニトロ基、低級アルキル
基、低級ハロアルキル基、低級アルコキシ基、低級ハロ
アルコキシ基、低級アルキルチオ基、低級アルキルスル
フィニル基、低級アルキルスルホニル基、低級ハロアル
キルチオ基、低級ハロアルキルスルフィニル基、低級ハ
ロアルキルスルホニル基、低級アルキニル基又は低級ア
ルコキシカルボニル基を示し、Zは同一又は異なっても
良く、ハロゲン原子、ニトロ基、シアノ基、低級アルキ
ル基、低級ハロアルキル基、低級アルコキシ基、低級ハ
ロアルコキシ基、低級アルキルチオ基、低級ハロアルキ
ルチオ基、低級アルキルスルフィニル基、低級ハロアル
キルスルフィニル基、低級アルキルスルホニル基、低級
ハロアルキルスルホニル基、低級ハロアルキルスルホニ
ルオキシ基、低級アルキルカルボニル基又はフェノキシ
基を示し、l、m及びnは各々0〜5の整数を示す。)
で表されるヒドラゾン誘導体。(1) General formula (I) (Wherein, R 1 , R 2 , R 3 and R 4 may be the same or different and each represents a hydrogen atom or a lower alkyl group; X may be the same or different; a halogen atom, a nitro group, a lower alkyl A lower haloalkyl group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfinyl group or a lower alkylsulfonyl group, Y may be the same or different, and a halogen atom, a cyano group, a nitro group, a lower alkyl group, a lower haloalkyl Group, lower alkoxy group, lower haloalkoxy group, lower alkylthio group, lower alkylsulfinyl group, lower alkylsulfonyl group, lower haloalkylthio group, lower haloalkylsulfinyl group, lower haloalkylsulfonyl group, lower alkynyl group or lower alkoxycarbonyl group , Z may be the same or different, and , Nitro group, cyano group, lower alkyl group, lower haloalkyl group, lower alkoxy group, lower haloalkoxy group, lower alkylthio group, lower haloalkylthio group, lower alkylsulfinyl group, lower haloalkylsulfinyl group, lower alkylsulfonyl group, lower haloalkyl It represents a sulfonyl group, a lower haloalkylsulfonyloxy group, a lower alkylcarbonyl group or a phenoxy group, and l, m and n each represent an integer of 0 to 5.)
A hydrazone derivative represented by
が同一又は異なっても良く、水素原子又は低級アルキル
基を示し、Xが同一又は異なっても良く、ハロゲン原
子、低級アルキル基、又は低級ハロアルキル基を示し、
Yが同一又は異なっても良く、シアノ基、ニトロ基、低
級アルキル基、低級ハロアルキル基、低級ハロアルキル
チオ基又は低級ハロアルキルスルフィニル基を示し、Z
が同一又は異なっても良く、ハロゲン原子、ニトロ基、
シアノ基、低級アルキル基、低級ハロアルキル基、低級
アルコキシ基又は低級ハロアルコキシ基を示し、l、m
及びnが各々0〜3の整数を示す請求項第1項記載のヒ
ドラゾン誘導体。2. In the general formula (I), R 1 , R 2 , R 3 and R 4
May be the same or different, represents a hydrogen atom or a lower alkyl group, X may be the same or different, represents a halogen atom, a lower alkyl group, or a lower haloalkyl group;
Y may be the same or different and represents a cyano group, a nitro group, a lower alkyl group, a lower haloalkyl group, a lower haloalkylthio group or a lower haloalkylsulfinyl group;
May be the same or different, a halogen atom, a nitro group,
A cyano group, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group or a lower haloalkoxy group;
The hydrazone derivative according to claim 1, wherein each of n and n represents an integer of 0 to 3.
が同一又は異なっても良く、水素原子又は低級アルキル
基を示し、Xが同一又は異なっても良く、ハロゲン原
子、低級アルキル基又は低級ハロアルキル基を示し、Y
が同一又は異なっても良く、シアノ基、ニトロ基又は低
級ハロアルキルスルフィニル基を示し、Zが同一又は異
なっても良く、ハロゲン原子、低級ハロアルキル基又は
低級ハロアルコキシ基を示し、l、m及びnが各々1〜
3の整数を示す請求項第2項記載のヒドラゾン誘導体。3. In the general formula (I), R 1 , R 2 , R 3 and R 4
May be the same or different and represents a hydrogen atom or a lower alkyl group; X may be the same or different and represents a halogen atom, a lower alkyl group or a lower haloalkyl group;
May be the same or different, represents a cyano group, a nitro group or a lower haloalkylsulfinyl group, Z may be the same or different, represents a halogen atom, a lower haloalkyl group or a lower haloalkoxy group, and l, m and n represent Each one
The hydrazone derivative according to claim 2, which represents an integer of 3.
Xが3位に置換し、少なくとも一個のYが4位に置換
し、少なくとも一個のZが4位に置換した請求項第3項
記載のヒドラゾン誘導体。4. The compound according to claim 3, wherein in formula (I), at least one X is substituted at the 3-position, at least one Y is substituted at the 4-position, and at least one Z is substituted at the 4-position. Hydrazone derivatives.
原子又は低級アルキル基を示し、R5はハロゲン原子又は
水酸基を示し, Xは同一又は異なっても良く、ハロゲン
原子、ニトロ基、低級アルキル基、低級ハロアルキル
基、低級アルコキシ基、低級アルキルチオ基、低級アル
キルスルフィニル基又は低級アルキルスルホニル基を示
し、Yは同一又は異なっても良く、ハロゲン原子、シア
ノ基、ニトロ基、低級アルキル基、低級ハロアルキル
基、低級アルコキシ基、低級ハロアルコキシ基、低級ア
ルキルチオ基、低級アルキルスルフィニル基、低級アル
キルスルホニル基、低級ハロアルキルチオ基、低級ハロ
アルキルスルフィニル基、低級ハロアルキルスルホニル
基、低級アルキニル基又は低級アルコキシカルボニル基
を示し、l及びmは各々0〜5の整数を示す。)で表さ
れる化合物と一般式(II) (式中、R4は水素原子又は低級アルキル基を示し、Zは
同一又は異なっても良く、ハロゲン原子、ニトロ基、シ
アノ基、低級アルキル基、低級ハロアルキル基、低級ア
ルコキシ基、低級ハロアルコキシ基、低級アルキルチオ
基、低級ハロアルキルチオ基、低級アルキルスルフィニ
ル基、低級ハロアルキルスルフィニル基、低級アルキル
スルホニル基、低級ハロアルキルスルホニル基、低級ハ
ロアルキルスルホニルオキシ基、低級アルキルカルボニ
ル基又はフェノキシ基を示し、nは0〜5の整数を示
す。)で表されるアニリン類と反応させることを特徴と
する一般式(I) (式中、R1、R2、R3、R4、X、Y、Z、l、m及びnは
前記に同じ。)で表されるヒドラゾン誘導体の製造方
法。5. A compound of the general formula (III) (Wherein, R 1 , R 2 and R 3 may be the same or different and each represent a hydrogen atom or a lower alkyl group; R 5 represents a halogen atom or a hydroxyl group; X may be the same or different; A nitro group, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfinyl group or a lower alkylsulfonyl group, Y may be the same or different, a halogen atom, a cyano group, a nitro group, Lower alkyl group, lower haloalkyl group, lower alkoxy group, lower haloalkoxy group, lower alkylthio group, lower alkylsulfinyl group, lower alkylsulfonyl group, lower haloalkylthio group, lower haloalkylsulfinyl group, lower haloalkylsulfonyl group, lower alkynyl group or Represents a lower alkoxycarbonyl group, and l and m are each Represents an integer of 0 to 5. The compound represented by) the formula (II) (Wherein, R 4 represents a hydrogen atom or a lower alkyl group; Z may be the same or different; a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group) A lower alkylthio group, a lower haloalkylthio group, a lower alkylsulfinyl group, a lower haloalkylsulfinyl group, a lower alkylsulfonyl group, a lower haloalkylsulfonyl group, a lower haloalkylsulfonyloxy group, a lower alkylcarbonyl group or a phenoxy group; A general formula (I) characterized by reacting with an aniline represented by the formula: (Wherein, R 1 , R 2 , R 3 , R 4 , X, Y, Z, 1, m, and n are the same as described above).
又は低級アルキル基を示し, Xは同一又は異なっても良
く、ハロゲン原子、ニトロ基、低級アルキル基、低級ハ
ロアルキル基、低級アルコキシ基、低級アルキルチオ
基、低級アルキルスルフィニル基又は低級アルキルスル
ホニル基を示し、Zは同一又は異なっても良く、ハロゲ
ン原子、ニトロ基、シアノ基、低級アルキル基、低級ハ
ロアルキル基、低級アルコキシ基、低級ハロアルコキシ
基、低級アルキルチオ基、低級ハロアルキルチオ基、低
級アルキルスルフィニル基、低級ハロアルキルスルフィ
ニル基、低級アルキルスルホニル基、低級ハロアルキル
スルホニル基、低級ハロアルキルスルホニルオキシ基、
低級アルキルカルボニル基又はフェノキシ基を示し、l
及びnはそれぞれ0〜5の整数を示す。)で表される化
合物と一般式(V) (式中、R1及びR2は同一又は異なっても良く、水素原子
又は低級アルキル基を示し, Yは同一又は異なっても良
く、ハロゲン原子、シアノ基、ニトロ基、低級アルキル
基、低級ハロアルキル基、低級アルコキシ基、低級ハロ
アルコキシ基、低級アルキルチオ基、低級アルキルスル
フィニル基、低級アルキルスルホニル基、低級ハロアル
キルチオ基、低級ハロアルキルスルフィニル基、低級ハ
ロアルキルスルホニル基、低級アルキニル基又は低級ア
ルコキシカルボニル基を示し、mは0〜5の整数を示
し、Hal はハロゲン原子を示す。)で表される化合物を
反応させることを特徴とする一般式(I) (式中 、R1、R2、R3、R4、X、Y、Z、l、m及びn
は前記に同じ。)で表されるヒドラゾン誘導体の製造方
法。6. Formula (IV) (Wherein, R 3 and R 4 may be the same or different and each represent a hydrogen atom or a lower alkyl group; X may be the same or different; and a halogen atom, a nitro group, a lower alkyl group, a lower haloalkyl group, a lower Represents an alkoxy group, a lower alkylthio group, a lower alkylsulfinyl group or a lower alkylsulfonyl group, Z may be the same or different, and a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower Haloalkoxy group, lower alkylthio group, lower haloalkylthio group, lower alkylsulfinyl group, lower haloalkylsulfinyl group, lower alkylsulfonyl group, lower haloalkylsulfonyl group, lower haloalkylsulfonyloxy group,
A lower alkylcarbonyl group or a phenoxy group,
And n each represent an integer of 0 to 5. ) And the general formula (V) (Wherein, R 1 and R 2 may be the same or different and each represent a hydrogen atom or a lower alkyl group; Y may be the same or different; a halogen atom, a cyano group, a nitro group, a lower alkyl group, a lower haloalkyl Group, lower alkoxy group, lower haloalkoxy group, lower alkylthio group, lower alkylsulfinyl group, lower alkylsulfonyl group, lower haloalkylthio group, lower haloalkylsulfinyl group, lower haloalkylsulfonyl group, lower alkynyl group or lower alkoxycarbonyl group , M represents an integer of 0 to 5, and Hal represents a halogen atom.) (Wherein, R 1 , R 2 , R 3 , R 4 , X, Y, Z, 1, m, and n
Is the same as above. )).
く、水素原子又は低級アルキル基を示し、Xは同一又は
異なっても良く、ハロゲン原子、ニトロ基、低級アルキ
ル基、低級ハロアルキル基、低級アルコキシ基、低級ア
ルキルチオ基、低級アルキルスルフィニル基又は低級ア
ルキルスルホニル基を示し、Yは同一又は異なっても良
く、ハロゲン原子、シアノ基、ニトロ基、低級アルキル
基、低級ハロアルキル基、低級アルコキシ基、低級ハロ
アルコキシ基、低級アルキルチオ基、低級アルキルスル
フィニル基、低級アルキルスルホニル基、低級ハロアル
キルチオ基、低級ハロアルキルスルフィニル基、低級ハ
ロアルキルスルホニル基、低級アルキニル基又は低級ア
ルコキシカルボニル基を示し、Zは同一又は異なっても
良く、ハロゲン原子、ニトロ基、シアノ基、低級アルキ
ル基、低級ハロアルキル基、低級アルコキシ基、低級ハ
ロアルコキシ基、低級アルキルチオ基、低級ハロアルキ
ルチオ基、低級アルキルスルフィニル基、低級ハロアル
キルスルフィニル基、低級アルキルスルホニル基、低級
ハロアルキルスルホニル基、低級ハロアルキルスルホニ
ルオキシ基、低級アルキルカルボニル基又はフェノキシ
基を示し、l、m及びnは各々0〜5の整数を示す。)
で表されるヒドラゾン誘導体を有効成分として含有する
ことを特徴とする農園芸用殺虫剤。7. The formula (I) (Wherein, R 1 , R 2 , R 3 and R 4 may be the same or different and each represents a hydrogen atom or a lower alkyl group; X may be the same or different; a halogen atom, a nitro group, a lower alkyl A lower haloalkyl group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfinyl group or a lower alkylsulfonyl group, Y may be the same or different, and a halogen atom, a cyano group, a nitro group, a lower alkyl group, a lower haloalkyl Group, lower alkoxy group, lower haloalkoxy group, lower alkylthio group, lower alkylsulfinyl group, lower alkylsulfonyl group, lower haloalkylthio group, lower haloalkylsulfinyl group, lower haloalkylsulfonyl group, lower alkynyl group or lower alkoxycarbonyl group , Z may be the same or different, and , Nitro group, cyano group, lower alkyl group, lower haloalkyl group, lower alkoxy group, lower haloalkoxy group, lower alkylthio group, lower haloalkylthio group, lower alkylsulfinyl group, lower haloalkylsulfinyl group, lower alkylsulfonyl group, lower haloalkyl It represents a sulfonyl group, a lower haloalkylsulfonyloxy group, a lower alkylcarbonyl group or a phenoxy group, and l, m and n each represent an integer of 0 to 5.)
A pesticide for agricultural and horticultural use, characterized by containing a hydrazone derivative represented by the following as an active ingredient.
が同一又は異なっても良く、水素原子又は低級アルキル
基を示し、Xが同一又は異なっても良く、ハロゲン原
子、低級アルキル基、又は低級ハロアルキル基を示し、
Yが同一又は異なっても良く、シアノ基、ニトロ基、低
級アルキル基、低級ハロアルキル基、低級ハロアルキル
チオ基又は低級ハロアルキルスルフィニル基を示し、Z
が同一又は異なっても良く、ハロゲン原子、ニトロ基、
シアノ基、低級アルキル基、低級ハロアルキル基、低級
アルコキシ基又は低級ハロアルコキシ基を示し、l、m
及びnが各々0〜3の整数を示す請求項第7項記載の農
園芸用殺虫剤。8. In the general formula (I), R 1 , R 2 , R 3 and R 4
May be the same or different, represents a hydrogen atom or a lower alkyl group, X may be the same or different, represents a halogen atom, a lower alkyl group, or a lower haloalkyl group;
Y may be the same or different and represents a cyano group, a nitro group, a lower alkyl group, a lower haloalkyl group, a lower haloalkylthio group or a lower haloalkylsulfinyl group;
May be the same or different, a halogen atom, a nitro group,
A cyano group, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group or a lower haloalkoxy group;
The agricultural and horticultural insecticide according to claim 7, wherein each of n and n represents an integer of 0 to 3.
が同一又は異なっても良く、水素原子又は低級アルキル
基を示し、Xが同一又は異なっても良く、ハロゲン原
子、低級アルキル基又は低級ハロアルキル基を示し、Y
が同一又は異なっても良く、シアノ基、ニトロ基又は低
級ハロアルキルスルフィニル基を示し、Zが同一又は異
なっても良く、ハロゲン原子、低級ハロアルキル基又は
低級ハロアルコキシ基を示し、l、m及びnが各々1〜
3の整数を示す請求項第8項記載の農園芸用殺虫剤。9. In the general formula (I), R 1 , R 2 , R 3 and R 4
May be the same or different and represents a hydrogen atom or a lower alkyl group; X may be the same or different and represents a halogen atom, a lower alkyl group or a lower haloalkyl group;
May be the same or different, represents a cyano group, a nitro group or a lower haloalkylsulfinyl group, Z may be the same or different, represents a halogen atom, a lower haloalkyl group or a lower haloalkoxy group, and l, m and n represent Each one
9. The insecticide for agricultural and horticultural use according to claim 8, which represents an integer of 3.
のXが3位に置換し、少なくとも一個のYが4位に置換
し、少なくとも一個のZが4位に置換している請求項第
9項記載の農園芸用殺虫剤。10. In the general formula (I), at least one X is substituted at the 3-position, at least one Y is substituted at the 4-position, and at least one Z is substituted at the 4-position. Agricultural and horticultural insecticides according to Item.
するために一般式(I) (式中、R1、R2、R3及びR4はは同一又は異なっても良
く、水素原子又は低級アルキル基を示し、Xは同一又は
異なっても良く、ハロゲン原子、ニトロ基、低級アルキ
ル基、低級ハロアルキル基、低級アルコキシ基、低級ア
ルキルチオ基、低級アルキルスルフィニル基又は低級ア
ルキルスルホニル基を示し、Yは同一又は異なっても良
く、ハロゲン原子、シアノ基、ニトロ基、低級アルキル
基、低級ハロアルキル基、低級アルコキシ基、低級ハロ
アルコキシ基、低級アルキルチオ基、低級アルキルスル
フィニル基、低級アルキルスルホニル基、低級ハロアル
キルチオ基、低級ハロアルキルスルフィニル基、低級ハ
ロアルキルスルホニル基、低級アルキニル基又は低級ア
ルコキシカルボニル基を示し、Zは同一又は異なっても
良く、ハロゲン原子、ニトロ基、シアノ基、低級アルキ
ル基、低級ハロアルキル基、低級アルコキシ基、低級ハ
ロアルコキシ基、低級アルキルチオ基、低級ハロアルキ
ルチオ基、低級アルキルスルフィニル基、低級ハロアル
キルスルフィニル基、低級アルキルスルホニル基、低級
ハロアルキルスルホニル基、低級ハロアルキルスルホニ
ルオキシ基、低級アルキルカルボニル基又はフェノキシ
基を示し、l、m及びnは各々0〜5の整数を示す。)
で表されるヒドラゾン誘導体を有効成分として含有する
農園芸用殺虫剤を、有効成分として10ア−ル当たり1
g 〜5kgの薬量で処理することを特徴とする望ましから
ぬ害虫の防除方法。11. Formula (I) for controlling useful crops from unwanted pests (Wherein, R 1 , R 2 , R 3 and R 4 may be the same or different and each represents a hydrogen atom or a lower alkyl group; X may be the same or different; a halogen atom, a nitro group, a lower alkyl A lower haloalkyl group, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfinyl group or a lower alkylsulfonyl group, Y may be the same or different, and a halogen atom, a cyano group, a nitro group, a lower alkyl group, a lower haloalkyl Group, lower alkoxy group, lower haloalkoxy group, lower alkylthio group, lower alkylsulfinyl group, lower alkylsulfonyl group, lower haloalkylthio group, lower haloalkylsulfinyl group, lower haloalkylsulfonyl group, lower alkynyl group or lower alkoxycarbonyl group , Z may be the same or different, and , Nitro group, cyano group, lower alkyl group, lower haloalkyl group, lower alkoxy group, lower haloalkoxy group, lower alkylthio group, lower haloalkylthio group, lower alkylsulfinyl group, lower haloalkylsulfinyl group, lower alkylsulfonyl group, lower haloalkyl It represents a sulfonyl group, a lower haloalkylsulfonyloxy group, a lower alkylcarbonyl group or a phenoxy group, and l, m and n each represent an integer of 0 to 5.)
An agricultural and horticultural insecticide containing as an active ingredient a hydrazone derivative represented by
A method for controlling unwanted pests, characterized in that the treatment is carried out at a dose of g to 5 kg.
R4が同一又は異なっても良く、水素原子又は低級アルキ
ル基を示し、Xが同一又は異なっても良く、ハロゲン原
子、低級アルキル基、又は低級ハロアルキル基を示し、
Yが同一又は異なっても良く、シアノ基、ニトロ基、低
級アルキル基、低級ハロアルキル基、低級ハロアルキル
チオ基又は低級ハロアルキルスルフィニル基を示し、Z
が同一又は異なっても良く、ハロゲン原子、ニトロ基、
シアノ基、低級アルキル基、低級ハロアルキル基、低級
アルコキシ基又は低級ハロアルコキシ基を示し、l、m
及びnが各々0〜3の整数を示す請求項第11項記載の
防除方法。12. In the general formula (I), R 1 , R 2 , R 3 and
R 4 may be the same or different, represents a hydrogen atom or a lower alkyl group, X may be the same or different, represents a halogen atom, a lower alkyl group, or a lower haloalkyl group;
Y may be the same or different and represents a cyano group, a nitro group, a lower alkyl group, a lower haloalkyl group, a lower haloalkylthio group or a lower haloalkylsulfinyl group;
May be the same or different, a halogen atom, a nitro group,
A cyano group, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group or a lower haloalkoxy group;
The control method according to claim 11, wherein each of n and n represents an integer of 0 to 3.
R4が同一又は異なっても良く、水素原子又は低級アルキ
ル基を示し、Xが同一又は異なっても良く、ハロゲン原
子、低級アルキル基又は低級ハロアルキル基を示し、Y
が同一又は異なっても良く、シアノ基、ニトロ基又は低
級ハロアルキルスルフィニル基を示し、Zが同一又は異
なっても良く、ハロゲン原子、低級ハロアルキル基又は
低級ハロアルコキシ基を示し、l、m及びnが各々1〜
3の整数を示す請求項第12項記載の防除方法。13. In the general formula (I), R 1 , R 2 , R 3 and
R 4 may be the same or different, represents a hydrogen atom or a lower alkyl group, X may be the same or different, represents a halogen atom, a lower alkyl group or a lower haloalkyl group, Y
May be the same or different, represents a cyano group, a nitro group or a lower haloalkylsulfinyl group, Z may be the same or different, represents a halogen atom, a lower haloalkyl group or a lower haloalkoxy group, and l, m and n represent Each one
13. The control method according to claim 12, wherein the control method represents an integer of 3.
のXが3位に置換し、少なくとも一個のYが4位に置換
し、少なくとも一個のZが4位に置換した請求項第13
項記載の防除方法。14. In the general formula (I), at least one X is substituted at the 3-position, at least one Y is substituted at the 4-position, and at least one Z is substituted at the 4-position.
The control method described in the section.
る請求項第14項記載の防除方法。15. The control method according to claim 14, wherein the pest is a lepidopteran pest or a Coleoptera pest.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP32951891A JP2879174B2 (en) | 1990-11-17 | 1991-11-18 | Hydrazone derivatives, their production, their uses and their use |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2-312414 | 1990-11-17 | ||
JP31241490 | 1990-11-17 | ||
JP32951891A JP2879174B2 (en) | 1990-11-17 | 1991-11-18 | Hydrazone derivatives, their production, their uses and their use |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH05262712A JPH05262712A (en) | 1993-10-12 |
JP2879174B2 true JP2879174B2 (en) | 1999-04-05 |
Family
ID=26567164
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP32951891A Expired - Fee Related JP2879174B2 (en) | 1990-11-17 | 1991-11-18 | Hydrazone derivatives, their production, their uses and their use |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP2879174B2 (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ZA949293B (en) * | 1993-12-08 | 1995-08-17 | Nihon Nohyaku Co Ltd | Hydrazine derivatives and uses thereof |
JP5093429B2 (en) * | 2000-10-18 | 2012-12-12 | 日本農薬株式会社 | Animal ectoparasite pest control agent and method of use |
JP4186182B2 (en) | 2002-01-10 | 2008-11-26 | 日本農薬株式会社 | Insecticides containing hydrazone derivatives as active ingredients and novel hydrazone derivatives |
-
1991
- 1991-11-18 JP JP32951891A patent/JP2879174B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JPH05262712A (en) | 1993-10-12 |
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