JPS6330472A - Imidazole based compound and pest controlling agent containing said compound - Google Patents
Imidazole based compound and pest controlling agent containing said compoundInfo
- Publication number
- JPS6330472A JPS6330472A JP61175274A JP17527486A JPS6330472A JP S6330472 A JPS6330472 A JP S6330472A JP 61175274 A JP61175274 A JP 61175274A JP 17527486 A JP17527486 A JP 17527486A JP S6330472 A JPS6330472 A JP S6330472A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compounds
- compound
- group
- blight
- 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.)
- Pending
Links
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 12
- 241000607479 Yersinia pestis Species 0.000 title claims abstract description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 title abstract description 58
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 3
- -1 imidazole compound Chemical class 0.000 claims description 26
- 239000000126 substance Substances 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 240000008067 Cucumis sativus Species 0.000 abstract description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 12
- 239000002904 solvent Substances 0.000 abstract description 9
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 abstract description 7
- 235000007688 Lycopersicon esculentum Nutrition 0.000 abstract description 7
- 239000002689 soil Substances 0.000 abstract description 7
- 240000003768 Solanum lycopersicum Species 0.000 abstract description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract description 5
- 241000233679 Peronosporaceae Species 0.000 abstract description 5
- 240000007594 Oryza sativa Species 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 4
- 235000020971 citrus fruits Nutrition 0.000 abstract description 3
- 235000009754 Vitis X bourquina Nutrition 0.000 abstract description 2
- 235000012333 Vitis X labruscana Nutrition 0.000 abstract description 2
- 240000006365 Vitis vinifera Species 0.000 abstract description 2
- 235000014787 Vitis vinifera Nutrition 0.000 abstract description 2
- 230000001717 pathogenic effect Effects 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 241000233622 Phytophthora infestans Species 0.000 abstract 3
- 230000001276 controlling effect Effects 0.000 abstract 2
- 230000001976 improved effect Effects 0.000 abstract 2
- 241000222235 Colletotrichum orbiculare Species 0.000 abstract 1
- 241001645342 Diaporthe citri Species 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 abstract 1
- 208000003351 Melanosis Diseases 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 244000052616 bacterial pathogen Species 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 230000002070 germicidal effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 24
- 238000009472 formulation Methods 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- 239000004563 wettable powder Substances 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 7
- 239000000969 carrier Substances 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
- 235000009849 Cucumis sativus Nutrition 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
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- 230000009036 growth inhibition Effects 0.000 description 5
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- 238000011081 inoculation Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- 244000068988 Glycine max Species 0.000 description 3
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- 229920001732 Lignosulfonate Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 235000013312 flour Nutrition 0.000 description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
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- 238000005507 spraying Methods 0.000 description 3
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- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 3
- 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 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-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
- 229920001817 Agar Polymers 0.000 description 2
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- 229920000742 Cotton Polymers 0.000 description 2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- 241000233866 Fungi Species 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- QQCGKIZHTJLRNN-NBRVCOCJSA-N Pipericine Chemical group CCCCCCCCCCCCC\C=C\C=C\C(=O)NCC(C)C QQCGKIZHTJLRNN-NBRVCOCJSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 244000088415 Raphanus sativus Species 0.000 description 2
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- 241001454293 Tetranychus urticae Species 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
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- 150000002576 ketones Chemical class 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical group O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
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- 241000219094 Vitaceae Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides 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
- 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
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 229940065181 bacillus anthracis Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical group CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 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
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 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
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical class C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 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
- 239000003085 diluting agent Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 description 1
- CKSHRDPCFLDKPV-UHFFFAOYSA-N diphenoxy-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1OP(=S)(S)OC1=CC=CC=C1 CKSHRDPCFLDKPV-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- JXIDLJPWUUDZFH-UHFFFAOYSA-J dizinc;n,n-dimethylcarbamodithioate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Zn+2].[Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S.[S-]C(=S)NCCNC([S-])=S JXIDLJPWUUDZFH-UHFFFAOYSA-J 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 244000013123 dwarf bean Species 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
- HEZNVIYQEUHLNI-UHFFFAOYSA-N ethiofencarb Chemical compound CCSCC1=CC=CC=C1OC(=O)NC HEZNVIYQEUHLNI-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 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
- 238000001914 filtration Methods 0.000 description 1
- 239000004467 fishmeal Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 235000021331 green beans Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000000366 juvenile effect Effects 0.000 description 1
- 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 1
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
- 229920000940 maneb Polymers 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 1
- 230000000813 microbial effect Effects 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
- 239000012046 mixed solvent Substances 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 244000000003 plant pathogen Species 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- QXJKBPAVAHBARF-UHFFFAOYSA-N procymidone Chemical class O=C1C2(C)CC2(C)C(=O)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 241000894007 species Species 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
- 239000007858 starting material Substances 0.000 description 1
- 229960005322 streptomycin Drugs 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
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明ｉ±新規なイミダゾール系化合物、それらを有効
成分として含有する有害生物防除剤に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to novel imidazole compounds and pest control agents containing them as active ingredients.
（発明の開示）
本発明の化合物は、下記一般式（１）で表わされる新規
なイミダゾール系化合物である。(Disclosure of the Invention) The compound of the present invention is a novel imidazole compound represented by the following general formula (1).
一般式：
（式中、Ｒ５及（／Ｒ，は水素原子、ハロゲン原子で置
換さにてもよいフルキル基、ハロゲン原子で置換されて
もよいフルケ二ル基又はハロゲン原子で置換されてもよ
いアルキニル基であり、Ｒ１とＲ１は窒素原子と共に複
数環を形成前記一般式（１，）中、Ｒ３及びＲ７で表わ
されるフルキル基、フルケニル基及びアルキニル基はハ
ロゲン原子で置換されていてもよく、そのハロゲン原子
としては塩素原子、弗素原子、臭素原子、沃素原子が挙
げられ、置換されるノ）ロデン原子の個数は１以上であ
って、特に１から５までが望ましい、またＲ１．Ｒ２及
びＲ３で表わされるアルキル基としては、メチル基、エ
チル基、プロピル基、ブチル基などが挙げられ。General formula: (wherein R5 and (/R, are hydrogen atoms, optionally substituted with a halogen atom, a furkyl group optionally substituted with a halogen atom, a fulkenyl group optionally substituted with a halogen atom, or a halogen atom optionally substituted with is an alkynyl group, and R1 and R1 form a plurality of rings together with a nitrogen atom In the general formula (1,), the furkyl group, fulkenyl group, and alkynyl group represented by R3 and R7 may be substituted with a halogen atom, Examples of the halogen atom include a chlorine atom, a fluorine atom, a bromine atom, and an iodine atom, and the number of substituted rhodene atoms is 1 or more, preferably 1 to 5. Examples of the alkyl group represented by include methyl group, ethyl group, propyl group, and butyl group.
Ｒ，及びＲ雪で表わされるフルケニル基としては、エチ
ニル基、プロペニル基、ブテニル基などが挙げら八、ア
ルキニル基としでは、エチン基、プロピン基、ブチン基
などが挙げら八る。Examples of the fulkenyl group represented by R and R include ethynyl group, propenyl group, butenyl group, etc., and examples of the alkynyl group include ethyne group, propyne group, butyne group, etc.
＊たＲ、 とＲ１は窒素原子と共にピペリシン環。*R, and R1 together with the nitrogen atom are pipericine rings.
ピペリシン環、モルフ中り′ン環、ピロリノン環などの
ような複−環を形成していてもよい。It may form a multiple ring such as a pipericine ring, a morphine ring, or a pyrrolinone ring.
本発明化合物は例えば次の方法によって製造することが
出来る。The compound of the present invention can be produced, for example, by the following method.
（Ａ）
（ｎ）
（ＩＩＩ）
（式中、Ｒ，、Ｒ，、Ｒ，及びＲ４は前述の通りであり
、Ｙはハロゲン原子である）前記反応（Ａ）及びＣＢ）
は必要に応じて溶媒及び酸受容体の存在下で行なわれる
。(A) (n) (III) (wherein R, , R, , R, and R4 are as described above, and Y is a halogen atom) the above reactions (A) and CB)
This is carried out in the presence of a solvent and an acid acceptor, if necessary.
前記反応（Ａ）に用いる溶媒としては例えばジオキサン
のようなエーテル類が挙げられ、酸受容体としては例え
ばトリエチルアミンのような有機塩基が挙げられる。Examples of the solvent used in the reaction (A) include ethers such as dioxane, and examples of the acid acceptor include organic bases such as triethylamine.
また、前記反応（Ｂ）に用いる溶媒としては。Moreover, as a solvent used in the reaction (B).
ベンゼン、トルエン、キシレン、クロロベンゼンなどの
芳香族炭化水素類：クロロホルム、四塩化炭素、塩化ノ
チレン、ジクロミニタン、トリクロロエタン、ｎ−ヘキ
サン、シクロヘキサンなどの環状又は非環状脂肪族炭化
水素ｍニジエチルエーテル、ジオキサン、テトラヒドロ
７ランなどのエーテルＭニア七トン、メチルエチルケト
ン、メチルイソブチルケトンなどのケトンＭニアセトニ
トリル、プロピオニドリル、７クリロニトリルなどのニ
トリルｍ： ジメチルホルム７ミド、Ｎ−メチルピロリ
ドン、ツメチルスルホキシド、スルホランなどの非プロ
トン性極性溶媒などが挙げられ、酸受容体としては例え
ば水酸化ナトリウム、水酸化カリウム、アルカリ金属も
しくはアルカリ土類金属の炭酸塩のような無機塩基、ト
リエチルアミンのような有機塩基が挙げられる。前記反
応ＣＢ）は適当な触媒の存在下でも行うことが出来る。Aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; cyclic or acyclic aliphatic hydrocarbons such as chloroform, carbon tetrachloride, notylene chloride, dichromitane, trichloroethane, n-hexane, and cyclohexane; mnidiethyl ether, dioxane, Ethers such as tetrahydro-7rane M Ketones such as methyl ethyl ketone, methyl isobutyl ketone M Nitriles such as niacetonitrile, propionidryl, 7-crylonitrile M: Dimethylform 7mide, N-methylpyrrolidone, trimethyl sulfoxide, sulfolane, etc. Examples of acid acceptors include inorganic bases such as sodium hydroxide, potassium hydroxide, alkali metal or alkaline earth metal carbonates, and organic bases such as triethylamine. . The reaction CB) can also be carried out in the presence of a suitable catalyst.
この触媒として、例えば４級アンモニウム塩誘導体のよ
うな相間移動触媒が挙げられる。Examples of this catalyst include phase transfer catalysts such as quaternary ammonium salt derivatives.
前記一般式（１）で表わされる化合物は、（１−ａ）（
Ｉｂ）
（式中、Ｒ１、Ｒｚ 、Ｒ３及びＲ１は前述の通りであ
る）を意味する。The compound represented by the general formula (1) is (1-a) (
Ib) (wherein R1, Rz, R3 and R1 are as defined above).
前記（Ａ）の反応において一般式（ＩＩ）で表わされる
化合物の２個のシアノ基のともらに硫化水素が反応する
かによって上記（Ｉ−ａ）及び／又は（１−ｂ）の生成
物を生じろ。Depending on whether hydrogen sulfide reacts with both of the two cyano groups of the compound represented by general formula (II) in the reaction of (A), the products of (I-a) and/or (1-b) may be produced. Arise.
前記（Ｂ）の反応において一般式（Ｉ［［）で表わされ
る化合物は、下記一般式（Ｉ［［−ａ）及び（ＩＩ−ｂ
）で表わされる互変異性体が存在するため、このもの
を原料物質として用いて本発明化合物を製造した場合、
（１−ａ）或いは（１−ｂ）、又はそれらの混合物を得
ることが出来る。In the reaction (B) above, the compound represented by the general formula (I[[) is a compound represented by the following general formula (I[[-a) and (II-b
) exists, so when the compound of the present invention is produced using this tautomer as a starting material,
(1-a) or (1-b) or a mixture thereof can be obtained.
（Ｉ［［−ａ） （Ｉ
−ｂ）前記一般式（１−ａ）で表わされる化合物と、（
１−ｂ）で表わされる化合物は、互いに異性体の関係に
あるが、両者を同時に表わすために本発明化合物は前記
一般式ＣＩ）で表示している。(I[[-a) (I
-b) a compound represented by the general formula (1-a), and (
The compounds represented by 1-b) are isomers of each other, but in order to represent both at the same time, the compound of the present invention is represented by the general formula CI).
前記一般式（１）の原料物質である前記 （ＩＩ）及び
ＣＩ［［）で表わされる化合物は、例えば次のようにし
て合成することが出来る。なお一般式（ＩＶ）の化合物
も互変異性体を有するが便宜上以下の通り表示する。The compounds represented by (II) and CI[[), which are the raw materials of the general formula (1), can be synthesized, for example, as follows. Although the compound of general formula (IV) also has tautomers, they are expressed as follows for convenience.
ＣＤ）
■
（１’／）
（式中、Ｒ，、Ｒ２、Ｒ，及びＹは前述の通りである）
上記一般式（ＩＶ）で表わされる化合物は例えば特開昭
５０−１２５０３１号公報に記載されて、公知のもので
ある。CD) ■ (1'/) (In the formula, R,, R2, R, and Y are as described above) The compound represented by the above general formula (IV) is described, for example, in JP-A-50-125031. This is a well-known method.
曲記一般式（Ｉ［）及び（Ｉ［［）で表わされる化合物
はほとんど新規化合物であり、その代表的化合物の化学
構造式を第１表及び第２表に挙げる。Most of the compounds represented by the general formulas (I[) and (I[[)] are new compounds, and the chemical structural formulas of representative compounds are listed in Tables 1 and 2.
次に本発明化合物の具体的合成例を記載する。Next, specific synthesis examples of the compounds of the present invention will be described.
合成例１． ４（５）−シアノ弓−ジメチルスル７７
モイル・２−メチル−５（４）・チオカルバモイルイミ
ダゾール（化合物ＮＯ。Synthesis example 1. 4(5)-cyanobow-dimethylsul77
Moyl 2-methyl-5(4) thiocarbamoylimidazole (compound NO.
２）の合成。2) Synthesis.
（１３４，５−ジシ７）・２・メチルイミグゾール１．
２ｇ及び１．３Ｂ、の無水炭酸カリウムを３０輸ａのア
セトニトリル中に加え、還流下に１時間攪拌した０次い
で室温まで冷却し、１．４４ｇのツメチルスル７アモイ
ルクａライドを加え再び加温し、還流下に２時間反応さ
せた。(134,5-disi7)-2-methyl imiguzole 1.
2g and 1.3B of anhydrous potassium carbonate were added to 30a of acetonitrile, stirred under reflux for 1 hour, then cooled to room temperature, added with 1.44g of trimethylsul7-ammoylchloride and warmed again. The reaction was carried out under reflux for 2 hours.
反応終了後、反応混合物を水中に投入し、酢酸エチルで
抽出し、水洗後無水硫酸ナトリウムで乾燥した。乾燥後
溶媒を減圧下に留去し、塩化メチレンをａＶＳ溶媒とし
てシリカゲルカラムクロマトグラフィーで精製し、融点
９２〜９５℃の４，５−ジシアノ−１−ツノチルスル７
アモイルー２−メチルイミグゾール１，２゜を得た。After the reaction was completed, the reaction mixture was poured into water, extracted with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. After drying, the solvent was distilled off under reduced pressure, and purified by silica gel column chromatography using methylene chloride as an aVS solvent.
Amoy-2-methylimigusol 1.2° was obtained.
（Ｉｆ） 前記工程（１）で得られた４、５−ジシア
ノ−１−ツメチルスル７７モイルー２・ノチルーイミダ
ゾール０．７７ｇ及びトリエチルアミン０．３３ｇを５
０ａｆｆのジオキサンに溶解し、攪拌しながら２０〜２
５℃で硫化水素ガスを導入し、室温で１時間反応させた
。(If) 0.77 g of 4,5-dicyano-1-tmethylsulfur 77 moy-2-notylimidazole obtained in the step (1) and 0.33 g of triethylamine were added to 5
Dissolve in dioxane of 0 aff and add 20 to 2 with stirring.
Hydrogen sulfide gas was introduced at 5°C, and the mixture was reacted at room temperature for 1 hour.
反応終了後、反応混合物を水中投入し、酢酸エチルで抽
出、水洗し、無水硫酸ナトリウムで乾燥した。乾燥後、
溶媒を減圧下に留去し、融点１６２〜１６５℃の目的物
０．７０．を得た７合成例２． ４．５・ノチオカル
パモイル・１−ジメチルスル７７モイルイミダゾール（
化合物Ｎｏ、６）の合成。After the reaction was completed, the reaction mixture was poured into water, extracted with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. After drying,
The solvent was distilled off under reduced pressure to obtain the desired product with a melting point of 162-165°C. 7 Synthesis Examples 2. 4.5-notiocarpamoyl-1-dimethylsul77moylimidazole (
Synthesis of compound No. 6).
（１３４，５−ジシアノイミダゾール
３．５４ｇ、ジエチルアミン０．２．及び乾燥ピリジン
５０輪ρを混合し攪拌しながら室温より硫化水素ガスを
導入し、徐々に温度を上げ４０−５０℃で１時間夏応さ
せた後そのまま２時間攪拌を続けた。(3.54g of 134,5-dicyanoimidazole, 0.2g of diethylamine, and 50 rings of dry pyridine were mixed, hydrogen sulfide gas was introduced from room temperature while stirring, and the temperature was gradually raised to 40-50℃ for 1 hour. After the mixture was allowed to react, stirring was continued for 2 hours.
反応終了後、反応混合物を水中投入し、次いで結晶を濾
取し、シリカゲルカラムクロマトグラフィーで精製し、
融点２２８〜２３２℃の４、Ｓ−５１チオカルパモイル
イミグゾール２．８４．を得た。After the reaction was completed, the reaction mixture was poured into water, and then the crystals were collected by filtration and purified by silica gel column chromatography.
4, S-51 thiocarpamoylimiguzole with melting point 228-232°C 2.84. I got it.
（ＩＩ） 前記工程ＣＩ）で得られた４、５−ジチオ
カルバモイルイミダゾール１．４ｇ及び無水炭酸カリウ
ム１．２ｇを３０ｍＮのアセトニトリル中に加え還流下
２時間攪拌した１次いで室温まで放冷し、１．２．のジ
メチルスル７７モイルクロリドを加えた後、再び還流下
で１時間攪拌した１反応終了後反応混合物を水中へ投入
し、酢酸エチルで抽出、次いで水洗し、無水゛硫酸ナト
リウムで乾燥した。乾燥後、減圧下に溶媒を留去し、得
られた残渣を１−ヘキサン／塩化ノチレンの混合溶媒で
洗浄後乾燥し、融点１７５〜１７８°℃の目的物１．２
２．を得た。(II) 1.4 g of 4,5-dithiocarbamoylimidazole obtained in step CI) and 1.2 g of anhydrous potassium carbonate were added to 30 mN acetonitrile and stirred under reflux for 2 hours. .2. After adding 77 moyl chloride of dimethylsulfate, the mixture was again stirred for 1 hour under reflux. After one reaction, the reaction mixture was poured into water, extracted with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. After drying, the solvent was distilled off under reduced pressure, and the resulting residue was washed with a mixed solvent of 1-hexane/notylene chloride and dried to obtain the desired product 1.2 with a melting point of 175-178°C.
2. I got it.
本発明化合物の代表例を第３表に挙げる。Representative examples of the compounds of the present invention are listed in Table 3.
上記第３表に記載されている代表化合物のうＳ
へＮｏ、６〜９は単一化合物（Ｒ，が−ｔ！Ｎｏ、基で
あるため、（Ｉ）の構造が面対称形となり、異性体が生
じない）であり、Ｎｏ、１〜５は、構造異性体の混合物
である。The representative compounds listed in Table 3 above, No. 6 to 9, are single compounds (R, is a -t! No. group, so the structure of (I) is plane symmetric, and isomerism No. 1 to 5 are mixtures of structural isomers.
本発明化合物は、有害生物防除剤として有用である。農
園芸用膜ｚ剤としては、稲いもち病、稲紋枯病、キュウ
リ炭そ病、キュウリうどんこ病、トマト疫病、トマト輪
紋病、柑橘類の黒点病、柑橘類のみどりかび病、ナシ黒
星病、リンゴ斑点落葉病、ブドウベと病、各種の灰色か
び病、菌核病。The compounds of the present invention are useful as pest control agents. Film Z agents for agriculture and horticulture include rice blast, rice sheath blight, cucumber anthracnose, cucumber powdery mildew, tomato late blight, tomato ring spot, citrus black spot, citrus green mold, and pear scab. , apple spot leaf blight, grape downy mildew, various botrytis diseases, and sclerotia.
さび病などの病害及びフザリウム国、ビシラム面。Diseases such as rust and Fusarium country, Bicilium surface.
リゾクトニア国、パーティシリウム国、プラズモディオ
ホーラ菌などの植物病原面によって引き起こされる土壌
病害に対し優れた防除効果を示し、特にジャガイモやト
マトの疫病、キュウリやブドウのぺと病、タバコの青か
び病、ビシラム菌による各種の土壌病害など藻菌類によ
る病害に対する防除効果が優れている９本発明化合物は
、予防効果のみならず治療効果も存しており、さらに優
れた浸透移行性を有していることから、土壌に処理する
ことによって、茎葉部の病害を防除する事が出来る。ま
た本発明化合物は除草活性も有しており、水田、畑地、
果ｍ面及び非農耕地用除草剤としても有用である。It shows excellent control effects against soil diseases caused by plant pathogens such as Rhizoctonia, Particillium, and Plasmodiophora, especially late blight on potatoes and tomatoes, downy mildew on cucumbers and grapes, and blue mold on tobacco. The 9 compounds of the present invention have excellent control effects against diseases caused by algae and fungi, including various soil diseases caused by Bicillum fungi. Therefore, by treating the soil, diseases on the stems and leaves can be controlled. The compound of the present invention also has herbicidal activity, and can be used in paddy fields, fields,
It is also useful as a herbicide for fruit crops and non-agricultural areas.
更に、前記一般式（■）及び（Ｉｌｌ）で表される中間
体も後期試験例に見る通り、有害生物防除剤として有用
なものである。Furthermore, the intermediates represented by the general formulas (■) and (Ill) are also useful as pest control agents, as shown in the late-stage test examples.
使用に際しては、従来の農薬製剤の場合と同様に、補助
剤と共に、乳剤、粉剤、水和剤、液剤などの種々の形態
に製剤することができる。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。ここに言う
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、安定剤などが挙げられ、
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、′ｆｌｉ黄粉末などの鉱物性粉末などが挙
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
等の酸アミド類、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金物類
などが挙げられる。When used, it can be formulated into various forms such as emulsions, powders, wettable powders, liquids, etc. together with adjuvants, as in the case of conventional agrochemical formulations. When these preparations are actually used, they can be used as they are, or they can be diluted to a predetermined concentration with a diluent such as water. The auxiliary agents mentioned here include carriers, emulsifiers, suspending agents, dispersants, spreading agents, penetrants, wetting agents, thickeners, stabilizers, etc.
Carriers that can be added as appropriate are divided into solid carriers and liquid carriers. Solid carriers include starch, activated carbon, soybean flour, wheat flour, wood flour, fish meal, animal and vegetable powders such as milk powder, talc, and kaolin. Examples of liquid carriers include water, alcohols such as methyl alcohol and ethylene glycol, acetone, Ketones such as methyl ethyl ketone, ethers such as dioxane and tetrahydrofuran, aliphatic hydrocarbons such as kerosene and kerosene, aromatic hydrocarbons such as xylene, trimethylbenzene, tetramethylbenzene, cyclohexane, and solvent naphtha, chloroform, chlorobenzene, etc. Examples include halogenated hydrocarbons, acid amides such as dimethylformamide, esters such as ethyl acetate and glycerin ester of fatty acids, nitrites such as acetonitrile, and sulfide-containing metals such as dimethyl sulfoxide.
本発明化合物の施用濃度は、対象作物、施用方法、製剤
形態、施用量などの違いによって異なり、−概に規定で
きないが、有効成分当たり、普通１〜１０．０００ ｐ
ｐｍ 、望ましくは、２０〜２，０００ ｐｐｍである
。The application concentration of the compound of the present invention varies depending on the target crop, application method, formulation form, application amount, etc. - Although it cannot be generally specified, it is usually 1 to 10,000 p per active ingredient.
pm, preferably 20 to 2,000 ppm.
また、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、抗ウィルス剤、誘引側、除草剤
、植物生長調整側などと、混用、併用することができ、
この場合には一層優れた効果を示すこともある。In addition, if necessary, it can be mixed or used in combination with other agricultural chemicals, such as insecticides, acaricides, nematicides, fungicides, antiviral agents, attractants, herbicides, plant growth regulators, etc. I can,
In this case, even better effects may be obtained.
例えば、殺虫剤、殺ダニ剤、或いは殺線虫剤としては、
０−（４−プロモー２−クロロフェニル） ０−エチル
Ｓ−プロピル ホスホロチオニー）、２．２−ジクロ
ロビニル ジメチル ホスフェート、エチル ３−メチ
ル−４−（メチルチオ）フェニル イソプロピルホスホ
ロアミデート、０．０−ジメチル ０−４−二トローｍ
−）リルホスホロチオエート、０−エチル ０−４−ニ
トロフェニル フェニルホスホノチオエート、０゜０−
ジエチル ０−２−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、０．０−ジメチル
Ｏ−（３，５，６−）リクロロー２−ピリジル） ホ
スホロチオエート、ｏ。For example, as an insecticide, acaricide, or nematicide,
0-(4-promo2-chlorophenyl) 0-ethyl S-propyl phosphorothiony), 2,2-dichlorovinyl dimethyl phosphate, ethyl 3-methyl-4-(methylthio)phenyl isopropyl phosphoroamidate, 0.0-dimethyl 0-4-nitro m
-) Lyl phosphorothioate, 0-ethyl 0-4-nitrophenyl phenylphosphonothioate, 0゜0-
Diethyl 0-2-isopropyl-6-methylpyrimidin-4-yl phosphorothioate, 0.0-dimethyl O-(3,5,6-)lichloro-2-pyridyl) phosphorothioate, o.
Ｓ−ジメチル 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） ０−エチル Ｓ−プ
ロピル ホスホロジチオエートのような有機リン酸エス
テル系化合物；１−ナフチルメチルカーパーメート、２
−イソプロポキシフェニルメチルカーバーメート、２−
メチル−２−（メチルチオ）プロピオンアルデヒド ０
−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 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〕〕と、スエクンイミド
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。S-Dimethyl acetyl phosphoramidothioate, O
-(2,4-dichlorophenyl) 0-ethyl S-propyl Organic phosphate ester compounds such as phosphorodithioate; 1-naphthylmethyl carpermate, 2
-isopropoxyphenylmethyl carbamate, 2-
Methyl-2-(methylthio)propionaldehyde 0
-Methylcarbamoyloxime, 2,3-dihydro-2
゜2-Dimethylbenzofuran-7-yl methyl carbamate, dimethyl N, N'-(thiobis[(methylimino)carbonyloxy]] and secunimidothioate, S-methyl N-(methylcarbamoyloxy)thioacetimidate ,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 メチルカーバメート、２−ジメチル
アミノ−５，６−シメチルピリミジンー４−イル ジメ
チルカーバメート、Ｓ。N'-dimethyl-2-methylcarbamoyloxyimino-2-(methylthio)acetamide, 2-(ethylthiomethyl)phenyl methylcarbamate, 2-dimethylamino-5,6-dimethylpyrimidin-4-yl dimethylcarbamate, S .
Ｓ’−２−ジメチルアミノトリメチレンビス（チオカー
バメ・−ト）のようなカーバメート系化合物；、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−クロロホルム７Ｌｚ２．４．５−
）ジクロロフェニル スルホンのような有機塩素系化合
物；トリシクロヘキシルチン ヒドロキシドのような冑
機金属系化合物；（ＲＳ）−α−シアノ−３−フェノキ
シベンジル（Ｒ３）−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 （ＩＨ
３）−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
、（Ｒ３）−α−シアノ−３−フェノキシベンジル （
ＩＨ３）−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、（Ｒ３）−α−シアノ−３−フェノキシベンジル
（ＩＨ３）−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、
（Ｒ３）−α−シアノ−３−フェノキシベンジル（ＩＲ
Ｓ）−シス、トランス−３−（２−クロロ−３，３，３
−）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のようなピレスロイド系化合
物；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Ｊレー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； ２ ｔａｒｔ−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−２
８−１，３，５−チアジアジン−４−オン、トランス−
５−（４−クロロフェニル）−Ｎ−シクロへキシル−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
）アミンのような化合物；イソプロピル（２Ｅ、４Ｅ）
−１１−メトキシ−３，７，１１−）ツメチル−２，４
−ドデカジノエートのような幼若ホルモン様化合物；ま
た、その他の化合物として、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などが挙
げられる。更に、ＢＴ剤、昆虫病原ウィルス剤などのよ
うな微生物農薬などと、混用、併用することもできる。Carbamate compounds such as S'-2-dimethylaminotrimethylenebis(thiocarbamate); 2.2
．． 2-Trichloro-1,1-bis(4-chloro,lophenyl)ethanol, 4-chloroform 7Lz2.4.5-
) Organochlorine compounds such as dichlorophenyl sulfone; metal compounds such as tricyclohexyltine hydroxide; (RS)-α-cyano-3-phenoxybenzyl (R3)-2-(4-chlorophenyl)-3
-Methylbutyrate, 3-phenoxybenzyl (IH
3)-cis, trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate, (R3)-α-cyano-3-phenoxybenzyl (
IH3)-cis, trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate, (R3)-α-cyano-3-phenoxybenzyl (IH3)-cis-3-(2 ,2-dibromovinyl)
-2,2-dimethylcyclopropane carboxylate,
(R3)-α-cyano-3-phenoxybenzyl (IR
S)-cis, trans-3-(2-chloro-3,3,3
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-2
, 4-difluorophenyl)-3-(2,6-difluorobenzoyl)urea; 2 tart-butylimino-3-isopropyl-5-phenyl-3,4°5.6-tetrahydro-2
8-1,3,5-thiadiazin-4-one, trans-
5-(4-chlorophenyl)-N-cyclohexyl-4
- Compounds such as methyl-2-oxothiazolidinone-3-carboxamide, N-methylbis(2,4-xylyliminomethyl)amine; isopropyl (2E, 4E)
-11-methoxy-3,7,11-)trimethyl-2,4
- Juvenile hormone-like compounds such as dodeccasinoate; Other compounds include dinitro compounds, organic sulfur compounds, urea compounds, triazine compounds, and the like. Furthermore, it can be mixed or used in combination with microbial pesticides such as BT agents and insect pathogenic virus agents.
例えば、殺国剤としては、Ｓ−ベンジル ０゜０−ジイ
ソプロピルホスホロチオエート、０−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を機リン系化
合物；４．ｓ、ｅ。For example, the nationalicides include S-benzyl 0゜0-diisopropyl phosphorothioate, 0-ethyl S, S-
3. Compounds such as diphenyl phosphorodithioate, aluminum ethyl hydrogen phosphonate; 4. s, e.
７−チ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
マンネブの錯化合物、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；３ａ、４゜７．
７ａ−テトラヒドロ−Ｎ−（）ジクロロメタンスルフェ
ニル）フタルイミド、３ａ、４，７゜７ａ−テトラヒド
ロ−Ｎ−（１，１，２，２−テトラクロロエタンスルフ
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、（Ｒ３） −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
；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−、（１）
１−１．２．４−）リアゾール−１−イル）ブタノン、
１− （ビフェニル−４−イルオキシ）−３，３−ジメ
チル−１−（ＩＨ−１，２，４−トリアゾール−１−イ
ル）ブタン−２−オール、１−ＣＮ−（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
トイミドイルコイミダゾール、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−ジクロ口フェニル）−４−
プロピル−°１．３−ジオキソランー２−イルメチル）
−１Ｈ−１，２，４−）リアゾール、１− （２−（２
，４−ジクロロフェニル）ペンチル）−１８−１，２，
４−）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
−（ＩＨ−１，２，４−）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；３゛−イソプロポキシ−〇−トルアニリド、α、
α、α−トリフルオロー３゛ −イソプロポキシ−０−
）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アシルアラニン
系化合物；３−クロロ−Ｎ−（３−クロロ−２，６−シ
ニトロー４−α、α、α−トリフルオロトリル）−５−
”−）リフルオロメチル−２−ビリジナミンのようなピ
リジナミン系化合物；またその他の化合物として、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、抗生物質な
どが挙げられる。Organochlorine compounds such as 7-titrachlorophthalide and tetrachloroisophthalonitrile; Manganese ethylene bis(dithiocarbamate) polymer, zinc ethylene bis(dithiocarbamate) polymer, complex compound of zinc and maneb, Dizinc bis(dimethyldithiocarbamate) ethylene bis(dithiocarbamate),
Dithiocarbamate compounds such as polymers of zinc propylene bis(dithiocarbamate); 3a, 4°7.
7a-tetrahydro-N-()dichloromethanesulfenyl)phthalimide, 3a,4,7゜7a-tetrahydro-N-(1,1,2,2-tetrachloroethanesulfenyl)phthalimide, N-(trichloromethylsulfenyl) N-halogenothioalkyl compounds such as phthalimide; 3-(3,5-dichlorophenyl)-N-
Isopropyl-2,4-dioxoimidazolidine-1-
Carboxamide, (R3) -3-(3,5-dichlorophenyl)-5-methyl-5-vinyl-1,3-oxazolidine-2,4-dione, N-(3,5-dichlorophenyl)-1,2 -dimethylcyclopropane-1,2
-Dicarboximide compounds such as dicarboximide; methyl 1-(butylcarbamoyl)benzimidazol-2-yl carbamate, dimethyl 4.4'
benzimidazole compounds such as -<O-phenylene)bis(3-thioallophanate); 1-(4-
chlorophenoxy)-3,3-dimethyl-1-, (1)
1-1.2.4-)riazol-1-yl)butanone,
1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(IH-1,2,4-triazol-1-yl)butan-2-ol, 1-CN-(4-chloro-2
-trifluoromethylphenyl)-2-propoxyacetimidoylcoimidazole, 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-1,2,4-) riazole, 1- (2-(2
,4-dichlorophenyl)pentyl)-18-1,2,
4-) Azole compounds such as lyazole; 2.4°
-dichloro-α-(pyrimidin-5-yl)benzhydryl alcohol, (±)-2,4° -difluoro-α
- Carbinol compounds such as (IH-1,2,4-)lyazol-1-ylmethyl)benzhydryl alcohol; 3'-isopropoxy-〇-toluanilide, α,
α,α-trifluoro3゛-isopropoxy-0-
) benzanilide-based compounds such as luanilide; acylalanine-based compounds such as methyl N-(2-methoxyacetyl)-N-(,2,6-xylyl)-DL-alaninate; 3-chloro-N-(3- Chloro-2,6-sinitro-4-α,α,α-trifluorotolyl)-5-
``-) Pyridinamine compounds such as lifluoromethyl-2-viridinamine; Other compounds include piperazine compounds, morpholine compounds, anthraquinone compounds, quinoxaline compounds, crotonic acid compounds, sulfenic acid compounds, Examples include urea compounds and antibiotics.
以下に、本発明に係わる試験例及び製剤例を記載する。Test examples and formulation examples related to the present invention are described below.
晋式 １ キュウリにと 防を
直径７．５ｃ■のポリ鉢でキュウリ （品種：四葉）を
栽培し、゛２葉期に達した時に、各供試化合物を所定濃
度に調整した薬液１０ｍｊをスプレーガンを用いて散布
した。２４〜２５℃の温室内に１昼夜保った後、ぺと病
菌の胞子懸濁液を噴霧接種した。接Ｊ１６日後に第１葉
の病斑面積率（Ｘ）を調査し、下記式により防除価を求
め、第４表の結果を得た。Shin method 1 Cultivate cucumbers (variety: four-leaf) in a plastic pot with a diameter of 7.5 cm, and when they reach the two-leaf stage, spray 10 mj of a chemical solution containing each test compound at a specified concentration. It was sprayed using a gun. After being kept in a greenhouse at 24-25° C. for one day and night, a spore suspension of P. mildew was inoculated by spraying. 16 days after inoculation, the lesion area ratio (X) on the first leaf was investigated, and the control value was calculated using the following formula, and the results shown in Table 4 were obtained.
２ キエ卸べと ｔｆｆＩＩ
直径７．５ｃ■のポリ鉢でキュウリ （品種；四葉）を
栽培し、２葉期に達した時に、べと病菌の胞子懸濁液を
噴霧接種した。６時間後に各供試化合物を所定濃度に調
整した薬液１０ｍｊをスプレーガンを用いて散布した。2. Kie Osorabeto tffII Cucumbers (variety: four-leaf) were grown in polyethylene pots with a diameter of 7.5 cm, and when they reached the two-leaf stage, they were spray inoculated with a spore suspension of downy mildew. After 6 hours, 10 mj of a chemical solution containing each test compound adjusted to a predetermined concentration was sprayed using a spray gun.
２４〜２５℃の温室内に６日間保つた後、第１葉の病斑
面積率（χ）を調査し、前記試験例１の場合と同様にし
、て防除価を求め、第５表の結果を得た。After being kept in a greenhouse at 24 to 25°C for 6 days, the lesion area ratio (χ) on the first leaf was investigated, and the control value was determined in the same manner as in Test Example 1, and the results are shown in Table 5. I got it.
第５表
１、例３ キュウリ段と ？ス゛■−１式直径７．５ｃ
ｍのポリ林でキュウリ （品種：四葉）を栽培し、２葉
期に達した時に、各供試化合物を所定濃度に調整した薬
液１０ｍＪをピペットを用いて土壌表面に潅注した。２
４〜２５℃の温室内に２日間保った後、べと病菌の胞子
懸濁液を噴霧接種した。接種６日後に第１葉の病斑面積
率（χ）を調査し、前記試験例１の場合と同様にして防
除価を求め、第６表の結果を得た。Table 5 1, Example 3 Cucumber tier? SW゛■-1 type diameter 7.5c
Cucumbers (variety: Yotsuba) were cultivated in a polygon forest of 1.5 m, and when they reached the 2-leaf stage, 10 mJ of a chemical solution containing each test compound adjusted to a predetermined concentration was applied to the soil surface using a pipette. 2
After being kept in a greenhouse at 4-25°C for 2 days, a spore suspension of downy mildew was inoculated by spraying. Six days after inoculation, the lesion area ratio (χ) on the first leaf was investigated, and the control value was determined in the same manner as in Test Example 1, and the results shown in Table 6 were obtained.
第６表
試 ４ トマト を果状
直径７．５ｃｍのポリ林でトマト （品種：ボンテロー
ザ）を栽培し、４葉期に達した時に、各供試化合物を所
定濃度に調整した薬液１０ｍｊをスプレーガンを用いて
散布した。２４〜２５℃の温室内に１昼夜保った後、疫
病菌の遊走子嚢懸濁液を噴霧接種した。接種５日後に病
斑数を調査し、下記式により防除価を求め、第７表の結
果を得た。Table 6 Test 4 Tomatoes (variety: Bonterosa) were cultivated in a poly forest with a fruit diameter of 7.5 cm, and when they reached the four-leaf stage, 10 mj of a chemical solution containing each test compound adjusted to a specified concentration was applied with a spray gun. It was sprayed using. After being kept in a greenhouse at 24 to 25°C for one day and night, a zoosporangium suspension of Phytophthora blight was spray inoculated. Five days after inoculation, the number of lesions was investigated, and the control value was calculated using the following formula, and the results shown in Table 7 were obtained.
第７表
試 ５ キュウ リ そ 防 果直
径７．５ｃｍ＋のポリ鉢でキュウリ （品種：四葉）を
栽培し、２葉期に達した時に、各供試化合物を所定濃度
に調整した薬ｆｉＬＯ＋ｍｆｆ１をスプレーガンを用い
て散布した。２４〜２５℃の温室内に１昼夜保った後、
炭そ病菌の胞子懸濁液を噴霧接種した。接種７日後に第
１葉の病斑数を調査し、前記試験例４の場合と同様にし
て防除価を求め、第８表の結果を得た。Table 7 Test 5 Cucumber Fruit Prevention Cultivate cucumbers (variety: four-leaf) in plastic pots with a diameter of 7.5 cm+, and when they reach the two-leaf stage, spray the drug fiLO+mff1 with each test compound adjusted to the specified concentration. It was sprayed using a gun. After keeping it in a greenhouse at 24-25℃ for one day and night,
A spore suspension of Bacillus anthracis was inoculated by spraying. Seven days after inoculation, the number of lesions on the first leaf was investigated, and the control value was determined in the same manner as in Test Example 4, and the results shown in Table 8 were obtained.
第８表
、 ６ ’ （＋
）１００ｐｐ−のストレプトマイシン及びｔｏｏｐｐ＊
の各有効成分化合物を含むバレイシラ・ブドウ糖寒天培
地（ＰＤＡ壇地）上に、前培養したキエウリ綿腐病Ｉｌ
ｌ （７ａ ｈａｎｉｄｅｒｍａｔｕｍ）のディスク（
寒天打抜）を移植した。２２℃で４８時間培養した後菌
叢直径を調査し、下記式によって菌糸生育阻害率（χ）
を求め、第９表の結果を得た。Table 8, 6' (+
) 100 pp- of streptomycin and toopp*
Chieuri cotton rot Il precultured on a Barley silla glucose agar medium (PDA platform) containing each of the active ingredient compounds.
l (7a hanidermatum) disc (
Agar punching) was transplanted. After culturing at 22°C for 48 hours, the bacterial flora diameter was investigated and the mycelial growth inhibition rate (χ) was calculated using the following formula.
The results shown in Table 9 were obtained.
第９表
７ ホ ルイ びウリカワｊ 試
１／１０．０ＯＯａボンドに水田土壌を詰め、ウリ゛カ
ワの塊茎を播種し、浅水状態に保った。その後３国に湛
水し、各供試化合物を有効成分で５０ｇ’／ａとなるよ
うに調整した薬液の所定量をピペットで滴下処理した。Table 9 7 Horui Bi Urikawaj Trial 1/10.0 OOa bond was filled with paddy soil, sown with Urikawa tubers, and maintained in shallow water conditions. Thereafter, the three countries were flooded with water, and a predetermined amount of a chemical solution containing each test compound adjusted to have an active ingredient of 50 g'/a was dropped using a pipette.
処理２０日後に生育状態を肉眼観察し、下記基準に従う
て生育抑制程度を求め、第１θ表の結果を得た。After 20 days of treatment, the growth state was observed with the naked eye, and the degree of growth inhibition was determined according to the following criteria, and the results shown in Table 1θ were obtained.
生育抑制程度の評価基準
第１０表
本発明化合物と同様に、前記一般式（■）及び（ＩＩＩ
）で表される中間体（第１表及び第２表）も有害生物防
除剤として有用である。以下にその試験例及び製剤例社
ついて記載する。Table 10 Evaluation Criteria for Degree of Growth Inhibition Similar to the compounds of the present invention, compounds of the general formula (■) and (III)
) (Tables 1 and 2) are also useful as pest control agents. The test examples and formulation companies are described below.
式 ８ キュウリベと −・防勿果状。Formula 8: Cucumber and - - Anti-fruitful state.
前記試験例１と同様にして、第１１表の結果を得た。The results shown in Table 11 were obtained in the same manner as in Test Example 1 above.
第１１表
量 、 ９ ト マ ト
° ｔ Ｊ
′前記試験例４と同様にして、第
１２表の結果を得た。Table 11: 9 tomatoes
° t J
'The results shown in Table 12 were obtained in the same manner as in Test Example 4 above.
前記試験例５と同様にして、第１３表の結果を得た。The results shown in Table 13 were obtained in the same manner as in Test Example 5 above.
第１３表 １１ 拭 （） 前記試験例６と同様にして、第１４表の結果を得た。Table 13 11 Wipe () The results shown in Table 14 were obtained in the same manner as in Test Example 6 above.
試 １２ ナミハダニ厚ダニム。Trial 12 Thick red spider mite.
直径７，５ｃｍのポリ林でインゲンマメ （品１１１：
江戸川菜豆）を栽培し、初生葉期に達した時に初生葉１
枚残して他の葉を切取った。ナミハダニの幼成虫（Ｄｉ
ｃｏｆｏｌ及び有機リン剤抵抗性）約３０頭を接種した
後、この苗を各供試化合物の所定６１度に調整した薬液
２０ｓ＋ｊに約１０秒間浸漬した。風乾後、２６℃の照
明付恒温器内に放置し、成虫２日後に生死を判定し下記
式により死出率（χ）を求め、第１５表の結果を得た。Green beans in a 7.5cm diameter pine forest (item 111:
Edogawa Namame) is cultivated, and when the first leaf stage is reached, the first leaf is 1.
I left one leaf and cut out the other leaves. Young adult two-spotted spider mite (Di
After inoculating about 30 seedlings (cofol and organic phosphorus agent resistance), the seedlings were immersed in a chemical solution 20s+j of each test compound adjusted to a predetermined temperature of 61 degrees for about 10 seconds. After air-drying, the insects were left in a constant temperature chamber with lighting at 26° C., and two days later, the survival rate (χ) was determined using the following formula, and the results shown in Table 15 were obtained.
第１５表 ４ １３ ヒメトビウンカ！ 試。Table 15 ４ 13 Red-bottomed planthopper! Trial.
各供試化合物の所定濃度の薬液２０ｍｊ！にイネ幼苗を
約１０秒間浸漬し、風乾した後湿った脱脂綿で根部を包
んで試験管に入れた０次いでこの中へヒメトビウンカの
成虫１０頭を放ち、管口をガーゼでふたをして、２６℃
の証明付恒温器内に放置した。成虫２日後に生死を判定
し、試験例１２の場合と同様にして死出率（χ）を求め
、第１６表の結果を得た。20 mj of chemical solution of each test compound at a specified concentration! After soaking rice seedlings in the water for about 10 seconds, air-drying them, wrapping the roots with moist absorbent cotton and placing them in a test tube.Next, 10 adult brown planthoppers were released into the test tube, and the opening of the tube was covered with gauze. ℃
It was left in a certified thermostat. Two days after the imagoes became adults, they were determined to be alive or dead, and the mortality rate (χ) was determined in the same manner as in Test Example 12, and the results shown in Table 16 were obtained.
試ＩＬＬ４ モモアカアブラムシ１ 。Trial ILL 4 Peach aphid 1.
各供試化合物の所定濃度に調整した薬液２０’ａＪに、
キャベツの葉片を約１０秒間浸漬し、風乾した直径９悄
のペトリ皿に湿った濾紙を置き、その上に風乾した葉片
を置いた。そこへモモアカアブラムシ無翅胎生雌虫を放
ち、ふたをして２６℃の照明付恒温器内に保った。成虫
２日後に生死を判定し、前記試験例１３の場合と同様に
して死出率（χ）を求め、第１７表の結果を得た。To 20'aJ of chemical solution adjusted to a predetermined concentration of each test compound,
Cabbage leaf pieces were immersed for about 10 seconds and air-dried. A wet filter paper was placed on a Petri dish with a diameter of 9 cm, and the air-dried leaf pieces were placed on top of the wet filter paper. Wingless viviparous female green peach aphids were released into the flask, which was then covered and kept in a lighted incubator at 26°C. Two days after the adult insects were grown, whether they were alive or dead was determined, and the mortality rate (χ) was determined in the same manner as in Test Example 13, and the results shown in Table 17 were obtained.
第１７表
、１５”１１ 草 八 式１／３，
０ＯＯａポットに畑地土壌を詰め、ヒエ、ダイコン及び
ダイズを１種した。その後、ヒエ、ダイコン、ダイズが
各々３葉期、２葉期、第１本葉期に達した時、各供試化
合物を２． ＯＯＯρｐａに”Ｊａｎシタ′ｒＡＷＬ＋
１０ ｓ＋ｊ ／ ；Ｎ ｙ トｇ葉処Ｎシタ。Table 17, 15”11 grass 8 formula 1/3,
A 0OOa pot was filled with field soil, and one species of barnyard grass, radish, and soybean was planted. Thereafter, when barnyard grass, radish, and soybean reached the three-leaf stage, two-leaf stage, and the first true leaf stage, respectively, each test compound was administered at 2. OOOρpa ni “Janshita’rAWL+
10 s + j / ; N y tog leaf treatment N site.
処理２０日後に生育状態を肉眼観察し、下記基準に基づ
いて生育抑制程度を調査し、第１８表の結果を得た。After 20 days of treatment, the growth state was observed with the naked eye, and the degree of growth inhibition was investigated based on the following criteria, and the results shown in Table 18 were obtained.
生育抑制程度の評価基準
第１８表
製剤例１
（イ）化合物Ｎｏ、 １ ５０重量部（ロ
）ジ−クライト ４Ｇ’−（ハ）リグ
ニンスルホン酸ソーダ ７ ＃（ニ）ジアルキルス
ルホサクシネート ３ ＃以上のものを均一に混合して
水和剤とした。Criteria for evaluating the degree of growth inhibition Table 18 Formulation example 1 (a) Compound No. 1 50 parts by weight (b) Di-cryte 4G'-(c) Sodium ligninsulfonate 7 #(d) Dialkyl sulfosuccinate 3 # or more The ingredients were mixed uniformly to make a wettable powder.
製剤例２
（イ）化合物Ｎｏ、２ ２０重量部（ロ）
ジ−クライト ７２ ＃（ハ）リグニ
ンスルホン酸ソーダ ８ ＃以上のものを均一に混
合して水和剤とした。Formulation Example 2 (a) Compound No. 2 20 parts by weight (b)
A wettable powder was prepared by homogeneously mixing 72 # (c) Sodium lignin sulfonate with 8 # or more of lignin sulfonate.
製剤例３
（イ）化合物Ｎｏ、 ３ ５重量部（
ロ）タルク ９５ ＃以上のも
のを均一に混合して水和剤とした。Formulation Example 3 (a) Compound No. 3 5 parts by weight (
b) Talc 95# or more was mixed uniformly to prepare a wettable powder.
製剤例４
（イ）化合物Ｎｏ、４ ２０重量部（ロ）
キシレン ６０ ＃（ハ）ポリオキ
シエチレンアルキル
アリルエーテル ２０ ＃以上の各成分
を混合、溶解して乳剤とした。Formulation Example 4 (a) Compound No. 4 20 parts by weight (b)
Xylene 60# (c) Polyoxyethylene alkyl allyl ether 20# The above components were mixed and dissolved to form an emulsion.
製剤例５
（イ） ジ−クライト ７８重量部（ロ）
β−ナフタレンスルホン酸ソーダホルマリン縮合物
２ 〃
（ハ） ポリオキシエチレンアルキル了りルサルフェー
ト ５ ＃（ニ） ホワイトカーボン
１５ ＃以上の各成分の混合物と、化合物Ｎ
ｏ、５ とを４８１の重量割合で混合し、水和剤とし
た。Formulation example 5 (a) 78 parts by weight of Sikurite (b)
β-Naphthalenesulfonic acid soda formalin condensate
2 (c) Polyoxyethylene alkyl sulfate 5 # (d) White carbon 15 # A mixture of each of the above components and compound N
o, 5 were mixed at a weight ratio of 481 to form a wettable powder.
製剤例６
（イ）化合物Ｎｏ、 ６ １重量部（
ロ）ベントナイト ６１ ＃（ハ）ジ
−クライト ３３ −（ニ）リグニンス
ルホン酸ソーダ ５１以上の各成分に適量の造粒所
要水を加え、混合、造粒して粒剤を得た。Formulation Example 6 (a) Compound No. 6 1 part by weight (
B) Bentonite 61 #(C) Di-Crite 33 -(D) Sodium ligninsulfonate 51 An appropriate amount of water required for granulation was added to each of the above components, and the mixture was mixed and granulated to obtain a granule.
製剤例７
（イ）中間体Ｎｏ、１ ５０重量部（ロ）
ジ−クライト ４０ ＃（ハ）リグ
ニンスルホン酸ソーダ ７ ＃（ニ）ジアルキルス
ルホサクシネート ３ ＃以上のものを均一に混合して
水和剤とした。Formulation Example 7 (a) Intermediate No. 1 50 parts by weight (b)
A wettable powder was prepared by uniformly mixing 40 #(c) of lignin sulfonate, 7 #(d) dialkyl sulfosuccinate, and 3 #(d) of dialkyl sulfosuccinate.
製剤例８
（イ）中間体Ｎｏ、２ ２０重量部（ロ）
ジ−クライト ７２ ＃（ハ）リグニ
ンスルホン酸ソーダ ８ ＃以上のものを均一に混
合して水和剤とした。Formulation Example 8 (a) Intermediate No. 2 20 parts by weight (b)
A wettable powder was prepared by homogeneously mixing 72 # (c) Sodium lignin sulfonate with 8 # or more of lignin sulfonate.
製剤例９
（イ）中間体Ｎｏ、 ３ ５重量部（
ロ）タルク ９５ ＃以上のも
のを均一に混合して水和剤とした。Formulation Example 9 (a) Intermediate No. 3 5 parts by weight (
b) Talc 95# or more was mixed uniformly to prepare a wettable powder.
製剤例１０
（イ）中間体Ｎｏ、４ ２０重量部（ロ）
キシレン ６０ ＃（ハ）ポリオ
キシエチレンアルキル
アリルエーテル ２ｏ ＃以上の各成分を
混合、溶解して乳剤とした。Formulation Example 10 (a) Intermediate No. 4 20 parts by weight (b)
Xylene 60 # (iii) Polyoxyethylene alkyl allyl ether 2 O # The above components were mixed and dissolved to form an emulsion.
製剤例１１
（イ） ジ−クライト ７８重量部（ロ
） β１ナフタレンスｌレホン酸ソーダホルマリン縮金
物 ２ ＃
（ハ） ポリオキシエチレンアルキルアリルサルフェー
ト ５ ＃（ニ） ホワイトカーボン
１５ ＃以上の各成分の混合物と、中間体
Ｎｏ、５ とを４：ｌの重量割合で混合し、水和剤と
した。Formulation Example 11 (a) Di-cryte 78 parts by weight (b) β1 naphthalene l sodium lephonate formalin condensate 2 # (c) Polyoxyethylene alkylallyl sulfate 5 # (d) White carbon 15 # of each of the above components The mixture and Intermediate No. 5 were mixed at a weight ratio of 4:1 to form a wettable powder.
製剤例１２
（イ）中間体Ｎｏ、 １０ １１１量部
（ロ）ベントナイト ６１ 〃（ハ
）ジ−クライト ３３ ＃（ニ）リグ
ニンスルホン酸ソーダ ５ ＃以上の各成分に適量
の造粒所要水を加え、混合、造粒して粒剤を得た。Formulation Example 12 (a) Intermediate No. 10 111 parts by weight (b) Bentonite 61 #(c) Zikrite 33 #(d) Sodium lignin sulfonate 5 # Add an appropriate amount of water required for granulation to each of the above components , mixed and granulated to obtain granules.
Claims (1)
置換されてもよいアルキル基、ハロゲン原子で置換され
てもよいアルケニル基又はハロゲン原子で置換されても
よいアルキニル基であり、Ｒ＿１とＲ＿２は窒素原子と
共に複素環を形成していてもよく、Ｒ＿３は水素原子又
はアルキル基であり、Ｒ＿４はシアノ基又は▲数式、化
学式、表等があります▼基である）で表わされるイミダ
ゾール系化合物。 ２、一般式： ▲数式、化学式、表等があります▼ （式中、Ｒ＿１及びＲ＿２は水素原子、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
てもよいアルケニル基又はハロゲン原子で置換されても
よいアルキニル基であり、Ｒ＿１とＲ＿２は窒素原子と
共に複素環を形成していてもよく、Ｒ＿３は水素原子又
はアルキル基であり、Ｒ＿４はシアノ基又は▲数式、化
学式、表等があります▼基である）で表わされるイミダ
ゾール系化合物を有効成分として含有することを特徴と
する有害生物防除剤。[Claims] 1. General formula: ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R_1 and R_2 are hydrogen atoms, alkyl groups that may be substituted with halogen atoms, or R_1 and R_2 may form a heterocycle together with a nitrogen atom, R_3 is a hydrogen atom or an alkyl group, and R_4 is a cyano group or an alkynyl group that may be substituted with a halogen atom. There are mathematical formulas, chemical formulas, tables, etc. An imidazole compound represented by the ▼ group. 2. General formulas: ▲ Numerical formulas, chemical formulas, tables, etc. R_1 and R_2 may form a heterocycle together with a nitrogen atom, R_3 is a hydrogen atom or an alkyl group, and R_4 is a cyano group or a ▲mathematical formula, chemical formula, table, etc. A pest control agent characterized by containing an imidazole compound represented by ▼ group) as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61175274A JPS6330472A (en) | 1986-07-25 | 1986-07-25 | Imidazole based compound and pest controlling agent containing said compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61175274A JPS6330472A (en) | 1986-07-25 | 1986-07-25 | Imidazole based compound and pest controlling agent containing said compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6330472A true JPS6330472A (en) | 1988-02-09 |
Family
ID=15993274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61175274A Pending JPS6330472A (en) | 1986-07-25 | 1986-07-25 | Imidazole based compound and pest controlling agent containing said compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6330472A (en) |
-
1986
- 1986-07-25 JP JP61175274A patent/JPS6330472A/en active Pending
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