JP2729810B2 - Phenyltriazole derivatives and insecticides - Google Patents
Phenyltriazole derivatives and insecticidesInfo
- Publication number
- JP2729810B2 JP2729810B2 JP63242881A JP24288188A JP2729810B2 JP 2729810 B2 JP2729810 B2 JP 2729810B2 JP 63242881 A JP63242881 A JP 63242881A JP 24288188 A JP24288188 A JP 24288188A JP 2729810 B2 JP2729810 B2 JP 2729810B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- atom
- alkyl
- formula
- trifluoromethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000002917 insecticide Substances 0.000 title claims description 12
- LUEYUHCBBXWTQT-UHFFFAOYSA-N 4-phenyl-2h-triazole Chemical class C1=NNN=C1C1=CC=CC=C1 LUEYUHCBBXWTQT-UHFFFAOYSA-N 0.000 title claims 3
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- -1 dimethylcarbamoyl group Chemical group 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000005079 alkoxycarbonylmethyl group Chemical group 0.000 claims description 3
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000004563 wettable powder Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 241000238631 Hexapoda Species 0.000 description 7
- 241001556089 Nilaparvata lugens Species 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 230000000749 insecticidal effect Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KINVSCCCUSCXTA-UHFFFAOYSA-N 1-phenyltriazole Chemical class N1=NC=CN1C1=CC=CC=C1 KINVSCCCUSCXTA-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 150000003852 triazoles Chemical group 0.000 description 5
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000254173 Coleoptera Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000254152 Sitophilus oryzae Species 0.000 description 2
- 241001454295 Tetranychidae Species 0.000 description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000007596 consolidation process Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000007855 nitrilimines Chemical class 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000005270 trialkylamine group Chemical group 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- ZMESHQOXZMOOQQ-UHFFFAOYSA-N 1-(naphthalen-1-ylmethyl)naphthalene Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZMESHQOXZMOOQQ-UHFFFAOYSA-N 0.000 description 1
- JATIYFMYXYMDTQ-UHFFFAOYSA-N 1-phenyl-3-(trifluoromethyl)-1,2,4-triazole Chemical compound N1=C(C(F)(F)F)N=CN1C1=CC=CC=C1 JATIYFMYXYMDTQ-UHFFFAOYSA-N 0.000 description 1
- OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- WOEYREDULCRSGY-UHFFFAOYSA-N 5-chloro-1,3-bis(2-chlorophenyl)-1,2,4-triazole Chemical compound ClC1=NC(C=2C(=CC=CC=2)Cl)=NN1C1=CC=CC=C1Cl WOEYREDULCRSGY-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241001414720 Cicadellidae Species 0.000 description 1
- 241001672694 Citrus reticulata Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000254171 Curculionidae Species 0.000 description 1
- 241001060517 Dicranolaius bellulus Species 0.000 description 1
- 241001466042 Fulgoromorpha Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 238000006736 Huisgen cycloaddition reaction Methods 0.000 description 1
- 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 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000256259 Noctuidae Species 0.000 description 1
- 241000320508 Pentatomidae Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000254062 Scarabaeidae Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- DBNLGTYGKCMLLR-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=CC=C(C(F)(F)F)C=C1 DBNLGTYGKCMLLR-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 150000001912 cyanamides Chemical class 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- PHHWLDOIMGFHOZ-UHFFFAOYSA-L disodium;dinaphthalen-1-ylmethanedisulfonate Chemical compound [Na+].[Na+].C1=CC=C2C(C(C=3C4=CC=CC=C4C=CC=3)(S(=O)(=O)[O-])S([O-])(=O)=O)=CC=CC2=C1 PHHWLDOIMGFHOZ-UHFFFAOYSA-L 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 150000004031 phenylhydrazines Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- XIPFMBOWZXULIA-UHFFFAOYSA-N pivalamide Chemical compound CC(C)(C)C(N)=O XIPFMBOWZXULIA-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000009885 systemic effect Effects 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
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
（産業上の利用分野） 本発明は１−フェニルトリアゾール誘導体及びこれを
有効成分として含有する殺虫剤に関するものである。 （従来の技術） これまで１−フェニル−３−トリフルオロメチル−1H
−1,2,4−トリアゾール（米国特許第4038405号公報明細
書）及び５−クロロ−1,3−ビス（２−クロロフェニ
ル）−1H−1,2,4−トリアゾール（特開昭62−19574号公
報明細書）が殺虫、殺ダニ剤として有効であることが知
られている。 （発明が解決しようとする課題） しかしながら、これらの化合物の殺虫効果は必ずしも
充分なものであるとはいえない。 本発明者らは更に有用な殺虫剤を開発すべく、種々の
１−フェニルトリアゾール誘導体を合成し、その生理活
性について検討を重ねた結果、本発明化合物が広範囲の
有害昆虫類に対し極めて優れた殺虫活性を有することを
見出し本発明を完成した。 （課題を解決するための手段） 本発明の１−フェニルトリアゾール誘導体は一般式
〔１〕 ｛式中、Ｘは塩素原子又はトリフルオロメチル基を示
し、Ｙはアルコキシ基、アルキルチオ基、アルキルスル
ホニル基、アリルチオ基、ジエチルアミノ基又はアルキ
ル基（該基はハロゲン原子、ジメチルカルバモイル基又
はアルコキシ基で置換されてもよい。）を示し、Ｚはア
ルケニル基、フェニル基（該基はフッ素原子、水酸基又
はメチル基で置換されてもよい。）、 式 （式中、R1とR2は、同一又は相異なり、水素原子、アル
キル基、アルコキシカルボニルメチル基を示す。）で表
される基、 式 ［式中、R3はアルキル基、フリル基、チエニル基又はフ
ェニル基（該基はハロゲン原子又はトリフルオロメチル
基で置換されてもよい。）を示す。］で表される基、１
−ピロリル基、アルケニルオキシ基、ピリジン−２−イ
ル基、エトキシメチリデンアミノ基、チエニルメチル
基、 式 （式中、Ａは酸素原子、硫黄原子又は窒素原子を示し、
R4は水素原子、ハロゲン原子、アルキル基又はニトロを
示す。）で表される基、グアニジル基、トリフルオロメ
チル基又はアルキル基を示す。 但し、 （ａ）Ｙが炭素数２〜６のアルキル基を示す場合には、
Ｚはアルケニル基、フェニル基（該基はフッ素原子、水
酸基又はメチル基で置換されている。）、アルコキシカ
ルボニルメチルアミノ基、 式 ［式中、R3はフリル基、チエニル基又はフェニル基（該
基はハロゲン原子又はトリフルオロメチル基で置換され
てもよい。）を示す。］で表される基、アルケニルオキ
シ基、ピリジン−２−イル基、チエニルメチル基、 式 （式中、Ａは酸素原子、硫黄原子又は窒素原子を示し、
R4は水素原子、ハロゲン原子、アルキル基又はニトロ基
を示す。）で表される基、グアニジル基又はアルキル基
を示し、 （ｂ）Ｙがアルコキシ基、アルキルチオ基、アルキルス
ルホニル基、アリルチオ基、ジエチルアミノ基、トリフ
ルオロメチル基、ジメチルカルバモイルアルキル基又は
アルコキシメチル基を示す場合に、Ｚはフェニル基、 式 （式中、R1とR2は、同一又は相異なり、水素原子、アル
キル基を示す。）で表される基、アルキルカルボニルア
ミノ基、１−ピロリル基、エトキシメチリデンアミノ基
又はトリフルオロメチル基を示す。｝で表される。 前記一般式〔１〕で表される本発明化合物を第１表に
例示する。尚、化合物番号は以後の記載において参照さ
れる。 本発明化合物は次の方法によって製造することができ
る。 ［式中、A1はハロゲン原子を示し、Y1はアルキル基（該
基はハロゲン原子、ジメチルカルバモイル基又はアルコ
キシ基で置換されてもよい。）を示し、Z1はアルキル
基、ハロゲン置換アルキル基、グアニジル基、フェニル
基（該基はフッ素原子、水酸基又はメチル基で置換され
てもよい。）、 式 （式中、R1及びR2は前記と同じ意味を示す。）で表され
る基を示し、Ｘは前記と同じ意味を示す。］ この方法では一般式〔２〕で示されるヒドラジドイル
ハライドと塩基とを反応させ、一般式〔３〕で示される
ニトリルイミン中間体を生成させる。生成したニトリル
イミン中間体を単離することなく、一般式〔４〕で示さ
れるニトリル類と1,3−シクロ付加反応させることによ
り目的とする一般式〔５〕で示される化合物を製造する
ことができる。 ここで使用できる塩基としては第三級アミン類、例え
ばトリアルキルアミン類、N,N−ジアルキルアニリン類
又はその他の芳香族アミン類等が挙げられ、１〜３倍モ
ル使用する。 この反応は無溶媒で又は不活性溶媒中で行うことがで
きる。溶媒としてはベンゼン、トルエン、キシレン等の
芳香族炭化水素類、クロロベンゼン、ジクロロベンゼン
等のハロゲン化芳香族炭化水素類、四塩化炭素、クロロ
ホルム、ジクロロメタン等のハロゲン化脂肪族炭化水素
類、ジエチルエーテル、テトラヒドロフラン等のエーテ
ル類が挙げられる。前記一般式〔４〕で示されるニトリ
ル類が液体の場合には、過剰のニトリル類を溶媒として
使用することもできる。 反応温度及び反応時間は、前記一般式〔２〕で示され
るヒドラジドイルハライドがヒドラジドイルブロミドの
場合は10〜80℃で0.5〜１時間反応させれば十分であ
り、ヒドラジドイルクロリドの場合は10℃から使用する
溶媒の沸点の温度範囲で、好ましくは室温から100℃で
１〜10時間反応させれば高収率で目的の化合物を製造す
ることができる。 ［式中、Y2はジエチルアミノ基又はアルキル基（該基は
ハロゲン原子、ジメチルカルバモイル基又はアルコキシ
基で置換されてもよい。）を示し、Z2はアルケニル基、
フェニル基（該基はフッ素原子、水酸基又はメチル基で
置換されてもよい。）、ピリジン−２−イル基、チエニ
ルメチル基、 式 （式中、Ａ及びR4は前記と同じ意味を示す。）で表され
る基又はアルキル基（該基はハロゲン原子又はアルコキ
シ基で置換されてもよい。）を示し、Ｘ及びA1は前記と
同じ意味を示す。］ この方法では、まず、一般式〔６〕で示されるヒドラ
ジドイルハライドとアンモニアとを水中又は不活性な溶
媒中で反応させ、一般式〔７〕で示される化合物を得
る。次にこれを一般式〔８〕で示されるカルボン酸ハラ
イドとを適当な塩基の存在下に反応させることにより、
一般式(Industrial application field) The present invention relates to a 1-phenyltriazole derivative and an insecticide containing the same as an active ingredient. (Prior art) 1-phenyl-3-trifluoromethyl-1H
1,2,4-triazole (U.S. Pat. No. 4,038,405) and 5-chloro-1,3-bis (2-chlorophenyl) -1H-1,2,4-triazole (Japanese Patent Application Laid-Open No. 62-19574) Is known to be effective as an insecticide and acaricide. (Problems to be solved by the invention) However, the insecticidal effect of these compounds is not always sufficient. The present inventors have synthesized various 1-phenyltriazole derivatives in order to develop more useful insecticides, and as a result of studying their physiological activities, the compounds of the present invention have been found to be extremely excellent against a wide range of harmful insects. The present inventors have found that they have insecticidal activity and completed the present invention. (Means for Solving the Problems) The 1-phenyltriazole derivative of the present invention has the general formula [1] In the formula, X represents a chlorine atom or a trifluoromethyl group, Y represents an alkoxy group, an alkylthio group, an alkylsulfonyl group, an allylthio group, a diethylamino group or an alkyl group (the group is a halogen atom, a dimethylcarbamoyl group or an alkoxy group). Z may be substituted with an alkenyl group, a phenyl group (the group may be substituted with a fluorine atom, a hydroxyl group or a methyl group); (Wherein, R 1 and R 2 are the same or different and each represent a hydrogen atom, an alkyl group, or an alkoxycarbonylmethyl group). [Wherein, R 3 represents an alkyl group, a furyl group, a thienyl group, or a phenyl group (the group may be substituted with a halogen atom or a trifluoromethyl group). A group represented by 1
-A pyrrolyl group, an alkenyloxy group, a pyridin-2-yl group, an ethoxymethylideneamino group, a thienylmethyl group, a formula (Where A represents an oxygen atom, a sulfur atom or a nitrogen atom,
R 4 represents a hydrogen atom, a halogen atom, an alkyl group or nitro. ), A guanidyl group, a trifluoromethyl group or an alkyl group. However, when (a) Y represents an alkyl group having 2 to 6 carbon atoms,
Z is an alkenyl group, a phenyl group (the group is substituted with a fluorine atom, a hydroxyl group or a methyl group), an alkoxycarbonylmethylamino group, a formula [In the formula, R 3 represents a furyl group, a thienyl group or a phenyl group (the group may be substituted with a halogen atom or a trifluoromethyl group). A alkenyloxy group, a pyridin-2-yl group, a thienylmethyl group, a group represented by the formula: (Where A represents an oxygen atom, a sulfur atom or a nitrogen atom,
R 4 represents a hydrogen atom, a halogen atom, an alkyl group or a nitro group. ), A guanidyl group or an alkyl group, and (b) Y represents an alkoxy group, an alkylthio group, an alkylsulfonyl group, an allylthio group, a diethylamino group, a trifluoromethyl group, a dimethylcarbamoylalkyl group or an alkoxymethyl group. Where Z is a phenyl group; (Wherein R 1 and R 2 are the same or different and each represent a hydrogen atom or an alkyl group), an alkylcarbonylamino group, a 1-pyrrolyl group, an ethoxymethylideneamino group or a trifluoromethyl Represents a group. It is represented by｝. The compounds of the present invention represented by the general formula [1] are exemplified in Table 1. The compound numbers will be referred to in the following description. The compound of the present invention can be produced by the following method. [In the formula, A 1 represents a halogen atom, Y 1 represents an alkyl group (the group may be substituted with a halogen atom, a dimethylcarbamoyl group or an alkoxy group.), And Z 1 represents an alkyl group or a halogen-substituted alkyl. Group, guanidyl group, phenyl group (the group may be substituted with a fluorine atom, a hydroxyl group or a methyl group), a formula (Wherein, R 1 and R 2 have the same meanings as described above), and X has the same meaning as described above. In this method, a hydrazideyl halide represented by the general formula [2] is reacted with a base to produce a nitrilimine intermediate represented by the general formula [3]. To produce a desired compound represented by the general formula [5] by subjecting a nitrile represented by the general formula [4] to 1,3-cycloaddition reaction without isolating the formed nitrileimine intermediate. Can be. Examples of the base that can be used here include tertiary amines, for example, trialkylamines, N, N-dialkylanilines, and other aromatic amines. This reaction can be carried out without solvent or in an inert solvent. As the solvent, benzene, toluene, aromatic hydrocarbons such as xylene, chlorobenzene, halogenated aromatic hydrocarbons such as dichlorobenzene, carbon tetrachloride, chloroform, halogenated aliphatic hydrocarbons such as dichloromethane, diethyl ether, Ethers such as tetrahydrofuran; When the nitrile represented by the general formula [4] is a liquid, an excess of the nitrile can be used as a solvent. The reaction temperature and the reaction time are sufficient if the hydrazideyl halide represented by the general formula [2] is hydrazidoyl bromide and the reaction is performed at 10 to 80 ° C for 0.5 to 1 hour. If the reaction is carried out at a temperature in the range of from 0 ° C. to the boiling point of the solvent used, preferably from room temperature to 100 ° C. for 1 to 10 hours, the desired compound can be produced in high yield. [In the formula, Y 2 represents a diethylamino group or an alkyl group (the group may be substituted with a halogen atom, a dimethylcarbamoyl group or an alkoxy group.), Z 2 represents an alkenyl group,
A phenyl group (the group may be substituted with a fluorine atom, a hydroxyl group or a methyl group), a pyridin-2-yl group, a thienylmethyl group, (Wherein, A and R 4 have the same meanings as described above) or an alkyl group (the group may be substituted with a halogen atom or an alkoxy group), and X and A 1 represent It has the same meaning as above. In this method, first, a hydrazideyl halide represented by the general formula [6] is reacted with ammonia in water or an inert solvent to obtain a compound represented by the general formula [7]. Next, this is reacted with a carboxylic acid halide represented by the general formula [8] in the presence of a suitable base, whereby
General formula
〔９〕で表される化合物を製造することができ
る。 本発明化合物のトリアゾール環の５位がエトキシメチ
リデンアミノ基の場合には、反応式−３に示す方法によ
り製造することができる。 （式中、R5はアルキル基を示し、Ｘ及びＹは前記と同じ
意味を示す。） 反応式−１にて製造した一般式〔10〕で示される５−
アミノ誘導体と一般式〔11〕で示されるオルトギ酸エス
テル類とを反応させることにより製造することができ
る。 本発明化合物のトリアゾール環の３位の置換基がアル
コキシ基、アルキルチオ基又はアリルチオ基の場合に
は、反応式−４に示す方法により製造することができ
る。 （式中、X1は酸素原子又は硫黄原子を示し、R6はアルキ
ル基又はアリル基を示し、Ｘ及びR5は前記と同じ意味を
示す。） 一般式〔13〕で示されるフェニルヒドラジン類と一般式
〔14〕で示されるシアナミド誘導体とを反応させること
により製造することができる。 本発明化合物のトリアゾール環の５位が 式 （式中、R3は前記と同じ意味を示す。）の場合には反応
式−５に示す方法により製造することができる。 （式中、Ｘ、Ｙ、A1及びR3は前記と同じ意味を示す。） 反応式−１又は反応式−４にて製造した一般式〔10〕
で示される５−アミノ誘導体と一般式〔16〕で示される
ハロゲン化合物とを塩基の存在下に反応させ一般式〔1
7〕で示される目的の化合物を製造することができる。 ここで使用できる塩基としては無機塩基又は第３級ア
ミン類、例えばトリアルキルアミン類、N,N−ジアルキ
ルアニリン類、芳香族アミン類又はアルコラート類等が
挙げられ、当モル以上使用することができる。液体の塩
基の場合は溶媒をかねて過剰に使用することもできる。
反応は適当な不活性溶媒中で行うこともできる。不活性
溶媒としては、例えばベンゼン、トルエン、キシレン等
の芳香族炭化水素類、四塩化炭素、クロロホルム、ジク
ロロメタン等の脂肪族ハロゲン化合物、ジエチルエーテ
ル、テトラヒドロフラン、ジオキサン等のエーテル類が
挙げられる。 本発明化合物のトリアゾール環の５位が１−ピロリル
基の場合には反応式−６に示す方法により製造すること
ができる。 （式中、Ｘ、Ｙ及びR5は前記と同じ意味を示す。） 反応式−１又は反応式−４にて製造した一般式〔10〕
で示される５−アミノ誘導体と一般式〔18〕で示される
テトラヒドロフラン誘導体とを反応させ一般式〔19〕で
示される５−ピロリル体を製造することができる。この
反応は不活性溶媒中で、室温から120℃の温度で0.5〜１
時間反応させれば収率良く目的物を製造することができ
る。 本発明化合物のトリアゾール環の３位がジメチルカル
バモイルアルキル基の場合には反応式−７に示す方法に
より製造することができる。 （式中、Ｘ、Ｚ及びR5は前記と同じ意味を示す。） 一般式〔20〕で示されるエステル体を、塩基等による
公知の方法で加水分解し、更にN,N′−カルボニルジイ
ミダゾール等と反応させた後、ジメチルアミンと反応さ
せ目的とする一般式〔22〕で示されるアミド化合物を製
造することができる。 次に、参考例及び実施例を挙げて具体的に本発明化合
物の製造法を説明する。 実施例 １ ５−アミノ−３−エチルチオ−１−（2,6−ジクロロ
−４−トリフルオロメチルフェニル）−1H−1,2,4−ト
リアゾールの製造（化合物番号29） 2,6−ジクロロ−４−トリフルオロメチルフェニルヒ
ドラジン4.9g（0.02モル）及びエチルチオメチリデンシ
アナミド3.8g（0.022モル）をエタノール50mlに溶か
し、８時間還流撹拌した。冷却した後、溶媒を留去し、
残渣をヘキサンで処理し、目的物を融点177〜179℃の白
色粉末として6.2g（収率87.3％）得た。 実施例 ２ ３−（1,1−ジメチルエチル）−５−（２−フリル）
−１−（2,6−ジクロロ−４−トリフルオロメチルフェ
ニル）−1H−1,2,4−トリアゾール（化合物番号15）の
製造 2,2−ジメチルプロピオンアミド 2,6−ジクロロ−４
−トリフルオロメチルフェニルヒドラゾン9.8g（0.03モ
ル）をピリジン50mlに溶かし、室温にて撹拌下２−フロ
イルクロリド4.3g（0.033モル）を滴下した。滴下終了
後、更に２時間還流下撹拌した。冷却させた後、反応液
を水中に注ぎ析出物を酢酸エチルにて抽出した。有機層
を５％塩酸、水の順で洗浄後、溶媒を留去した。残渣を
カラムクロマトグラフィーにて精製し、目的物を融点42
〜45℃の白色プリズム結晶として10.5g（収率86.8％）
得た。 実施例 ３ ３−エチルチオ−５−エトキシメチリデンアミノ−１
−（2,6−ジクロロ−４−トリフルオロメチルフェニ
ル）−1H−1,2,4−トリアゾール（化合物番号30）の製
造 ５−アミノ−３−エチルチオ−１−（2,6−ジクロロ
−４−トリフルオロメチルフェニル）−1H−1,2,4−ト
リアゾール3.6g（0.01モル）をオルトギ酸エチル10mlに
溶かし、１時間還流下撹拌した。冷却させた後、過剰の
オルトギ酸エチルを留去し、残渣をカラムクロマトグラ
フィーにて精製し、目的物を融点38〜39℃の白色プリズ
ム結晶として3.8g（収率92.0％）得た。 本発明の殺虫剤は前記１−フェニルトリアゾール誘導
体を有効成分として含有し、本誘導体のみ又はこれに各
種補助剤、例えば希釈剤、溶剤、界面活性剤等を配合し
て、乳剤、水和剤、粉剤、微粒剤又は粒剤等に製剤化し
てなる。希釈剤の例としてはクレー、タルク、ベントナ
イト、珪藻土、ホワイトカーボン等が挙げられる。溶剤
の例としてはシクロヘキサノン、キシレン、トルエン、
メチルエチルケトン、２−プロパノール、メチルナフタ
レン、ジメチルナフタレン等が挙げられる。界面活性剤
の例としてはアルキルベンゼンスルホン酸金属塩、ポリ
オキシエチレンアルキルアリールエーテル、アルキル硫
酸ナトリウム、ジナフチルメタンジスルホン酸金属塩、
アルキルナフタレンスルホン酸金属塩、リグニンスルホ
ン酸金属塩等が挙げられる。その他の補助剤としてはカ
ルボキシメチルセルロース、ポリエチレングリコール、
アラビアゴム等が挙げられる。 有効成分の配合割合については必要に応じ適宜選ばれ
るが、粉剤又は粒剤とする場合は0.1〜20％（重量）、
乳剤又は水和剤とする場合は５〜80％（重量）が適当で
ある。 使用に際しては適当な濃度に希釈して散布するか又は
直接施用する。 本発明の殺虫剤は茎葉散布、土壌施用、育苗箱施用又
は水面施用等により使用することができる。その施用量
は使用される化合物の種類、対象害虫、発生傾向、被害
の程度、環境条件、使用する剤型等によってかわるが、
粉剤及び粒剤のようにそのまま使用する場合は有効成分
で10アール当り0.1g〜5Kg、好ましくは1g〜1Kgの範囲か
ら適宜選ぶのがよい。また乳剤及び水和剤とする場合の
ように液状で使用する場合は0.1〜10,000ppm、好ましく
は10〜3,000ppmの範囲から適宜選ぶのがよい。 本発明の殺虫剤は他の殺虫剤、殺菌剤を混合して使用
することもできる。 次に本発明の殺虫剤の実施例を挙げて具体的に説明す
る。下記実施例中の％は重量百分率を示す。 実施例 ４ 乳剤 化合物番号（11）30％、シクロヘキサノン20％、ポリ
オキシエチレンアルキルアリールエーテル11％、アルキ
ルベンゼンスルホン酸カルシウム４％及びメチルナフタ
リン35％を均一に溶解して乳剤とした。 実施例 ５ 水和剤 化合物番号（15）40％、珪藻土15％、クレー15％、ホ
ワイトカーボン25％、ジナフチルメタンジスルホン酸ナ
トリウム２％及びリグニンスルホン酸ナトリウム３％を
均一に混合し粉砕して水和剤とした。 実施例 ６ 粉剤 化合物番号（20）２％、珪藻土５％及びクレー93％を
均一に混合し粉砕して粉剤とした。 実施例 ７ 粒剤 化合物番号（29）５％、ラウリルアルコール硫酸エス
テルのナトリウム塩２％、リグニンスルホン酸ナトリウ
ム５％、カルボキシメチルセルロース２％及びクレー86
％を均一に混合粉砕する。この混合物100重量部に水20
重量部を加えて練合し、押出式造粒機を用いて14〜32メ
ッシュの粒状に加工した後、乾燥して粒剤とした。 （発明の効果） 本発明の１−フェニルトリアゾール誘導体はトビイロ
ウンカ、セジロウンカ及びヒメトビウンカ等のウンカ類
及びイネミズゾウムシ、イネドロオイムシ等の甲虫類に
対して極めて優れた殺虫活性を有するとともに極めて優
れた浸透性殺虫活性を有する。更にヨコバイ類、アブラ
ムシ類、カメムシ類等の半翅目、コナガ、ハスモンヨト
ウ類の鱗翅目、イエバイ、アカイエカ等の双翅目、アズ
キゾウムシ、コガネムシ類等の鞘翅目、チャバネゴキブ
リ等の直翅目害虫及びナミハダニ、ミカンハダニ等のハ
ダニ類の防除にも有効である。 次に本発明の殺虫剤の奏する効果を試験例をもって説
明する。 試験例 １ トビイロウンカ殺虫試験 実施例５に準じて調製した水和剤を水で希釈した。こ
の薬液に稲茎葉を浸漬し、風乾後、試験管に静置した。
その中にトビイロウンカ幼虫10頭を放ち、脱脂綿で栓を
した。その後、25℃の恒温室に置き、６日後に死虫数を
調査し、死虫率を算出した。試験は２連制で行った。結
果を第２表及び第３表に示す。 以後の試験においても同様である。 試験例２ イネミズゾウムシ殺虫試験 実施例５に準じて調製した水和剤を有効成分で10ppm
の濃度に水で希釈した。この薬液を直径90mmのポリエチ
レン製カップに入れた。その中にイネミズゾウムシ成虫
10頭を放ち、蓋をした。その後、25℃の恒温室に置き、
２日後に死虫数を調査し、死虫率を算出した。試験は２
連制で行った。結果を第４表に示す。 試験例３ コナガ殺虫試験 実施例５に準じて調製した水和剤を有効成分で500ppm
の濃度に水で希釈した。この薬液にキャベツ葉を浸漬
し、風乾した後、径55mmのポリエチレン製カップに入れ
た。その中にコナガ３齢幼虫10頭を放ち、蓋をした。そ
の後、25℃の恒温室に置き、３日後に死虫数を調査し、
死虫率を算出した。試験は２連制で行った。結果を第５
表に示す。 試験例 ４ ヒメトビウンカ浸透性殺虫試験 実施例５に準じて調製した水和剤を有効成分濃度が10
ppmになるように水で希釈した。この薬液を瓶の中に入
れ、その中に稲苗の根部を浸漬し、苗をゴム栓で固定し
た後、金網円筒をかけた。その中にヒメトビウンカ雌幼
虫10頭を入れ蓋をした。その後、25℃の恒温室に置き、
２日後に死虫数を調査し、死虫率を算出した。試験は２
連制で行った。結果を第６表に示す。 The compound represented by [9] can be produced. When the 5-position of the triazole ring of the compound of the present invention is an ethoxymethylideneamino group, it can be produced by the method shown in Reaction Scheme-3. (In the formula, R 5 represents an alkyl group, and X and Y have the same meanings as described above.) 5- represented by the general formula [10] produced by the reaction formula-1
It can be produced by reacting an amino derivative with an orthoformate represented by the general formula [11]. When the 3-position substituent on the triazole ring of the compound of the present invention is an alkoxy group, an alkylthio group or an allylthio group, it can be produced by the method shown in Reaction Scheme-4. (In the formula, X 1 represents an oxygen atom or a sulfur atom, R 6 represents an alkyl group or an allyl group, and X and R 5 have the same meanings as described above.) Phenylhydrazines represented by the general formula [13] And a cyanamide derivative represented by the general formula [14]. The 5-position of the triazole ring of the compound of the present invention has the formula (Wherein R 3 has the same meaning as described above), and can be produced by the method shown in Reaction Scheme-5. (In the formula, X, Y, A 1 and R 3 have the same meanings as described above.) The general formula [10] produced by Reaction Formula-1 or Reaction Formula-4
Is reacted with a halogen compound represented by the general formula [16] in the presence of a base to form a compound represented by the general formula [1
7] can be produced. Examples of the base that can be used here include inorganic bases or tertiary amines, such as trialkylamines, N, N-dialkylanilines, aromatic amines or alcoholates, and can be used in equimolar or more. . In the case of a liquid base, the solvent can also be used in excess.
The reaction can also be performed in a suitable inert solvent. Examples of the inert solvent include aromatic hydrocarbons such as benzene, toluene, and xylene; aliphatic halogen compounds such as carbon tetrachloride, chloroform, and dichloromethane; and ethers such as diethyl ether, tetrahydrofuran, and dioxane. When the 5-position of the triazole ring of the compound of the present invention is a 1-pyrrolyl group, it can be produced by the method shown in Reaction Scheme-6. (In the formula, X, Y and R 5 have the same meanings as described above.) The general formula [10] produced by Reaction Formula-1 or Reaction Formula-4
Is reacted with a tetrahydrofuran derivative represented by the general formula [18] to produce a 5-pyrrolyl compound represented by the general formula [19]. The reaction is carried out in an inert solvent at a temperature between room temperature and 120.degree.
If the reaction is carried out for a long time, the desired product can be produced in good yield. When the 3-position of the triazole ring of the compound of the present invention is a dimethylcarbamoylalkyl group, it can be produced by the method shown in Reaction Scheme-7. (Wherein, X, Z and R 5 are as defined above.) General formula ester represented by [20] was hydrolyzed in a known manner with a base or the like, N, N'-carbonyldiimidazole After reacting with imidazole or the like, the desired amide compound represented by the general formula [22] can be produced by reacting with dimethylamine. Next, the production method of the compound of the present invention will be specifically described with reference to Reference Examples and Examples. Example 1 Production of 5-amino-3-ethylthio-1- (2,6-dichloro-4-trifluoromethylphenyl) -1H-1,2,4-triazole (Compound No. 29) 2,6-dichloro- 4.9 g (0.02 mol) of 4-trifluoromethylphenylhydrazine and 3.8 g (0.022 mol) of ethylthiomethylidene cyanamide were dissolved in 50 ml of ethanol, and the mixture was stirred under reflux for 8 hours. After cooling, the solvent is distilled off,
The residue was treated with hexane to obtain 6.2 g (yield: 87.3%) of the desired product as a white powder having a melting point of 177 to 179 ° C. Example 2 3- (1,1-dimethylethyl) -5- (2-furyl)
Preparation of -1- (2,6-dichloro-4-trifluoromethylphenyl) -1H-1,2,4-triazole (Compound No. 15) 2,2-dimethylpropionamide 2,6-dichloro-4
-9.8 g (0.03 mol) of trifluoromethylphenylhydrazone was dissolved in 50 ml of pyridine, and 4.3 g (0.033 mol) of 2-furoyl chloride was added dropwise with stirring at room temperature. After completion of the dropwise addition, the mixture was further stirred under reflux for 2 hours. After cooling, the reaction solution was poured into water, and the precipitate was extracted with ethyl acetate. After the organic layer was washed with 5% hydrochloric acid and water in that order, the solvent was distilled off. The residue was purified by column chromatography.
10.5 g (yield 86.8%) as white prism crystals at ~ 45 ° C
Obtained. Example 3 3-Ethylthio-5-ethoxymethylideneamino-1
Preparation of-(2,6-dichloro-4-trifluoromethylphenyl) -1H-1,2,4-triazole (Compound No. 30) 5-amino-3-ethylthio-1- (2,6-dichloro-4 -Trifluoromethylphenyl) -1H-1,2,4-triazole (3.6 g, 0.01 mol) was dissolved in ethyl orthoformate (10 ml) and stirred under reflux for 1 hour. After cooling, excess ethyl orthoformate was distilled off, and the residue was purified by column chromatography to obtain 3.8 g (yield: 92.0%) of the target product as white prism crystals having a melting point of 38 to 39 ° C. The insecticide of the present invention contains the 1-phenyltriazole derivative as an active ingredient, and blends the derivative alone or various auxiliary agents, such as a diluent, a solvent, a surfactant, etc., with an emulsion, a wettable powder, It is formulated into powders, fine granules or granules. Examples of diluents include clay, talc, bentonite, diatomaceous earth, white carbon, and the like. Examples of solvents include cyclohexanone, xylene, toluene,
Methyl ethyl ketone, 2-propanol, methyl naphthalene, dimethyl naphthalene and the like can be mentioned. Examples of the surfactant include alkyl benzene sulfonic acid metal salt, polyoxyethylene alkyl aryl ether, sodium alkyl sulfate, and dinaphthyl methane disulfonic acid metal salt.
Alkyl naphthalene sulfonic acid metal salts, lignin sulfonic acid metal salts and the like can be mentioned. Other auxiliaries include carboxymethylcellulose, polyethylene glycol,
Gum arabic and the like. The mixing ratio of the active ingredient is appropriately selected as necessary, but when the powder or granule is used, 0.1 to 20% (weight)
When it is used as an emulsion or a wettable powder, it is suitably from 5 to 80% (by weight). When used, they are diluted to an appropriate concentration and sprayed or applied directly. The insecticide of the present invention can be used by foliage application, soil application, nursery box application or water surface application. The application rate varies depending on the type of the compound used, the target pest, the occurrence tendency, the degree of damage, the environmental conditions, the dosage form used, etc.
When used as such as powders and granules, the active ingredient is appropriately selected from the range of 0.1 g to 5 kg, preferably 1 g to 1 kg per 10 ares. When used in the form of a liquid such as an emulsion and a wettable powder, it may be appropriately selected from the range of 0.1 to 10,000 ppm, preferably 10 to 3,000 ppm. The insecticide of the present invention can be used by mixing other insecticides and fungicides. Next, examples of the insecticide of the present invention will be specifically described. % In the following Examples shows a weight percentage. Example 4 Emulsion An emulsion was prepared by uniformly dissolving 30% of compound number (11), 20% of cyclohexanone, 11% of polyoxyethylene alkylaryl ether, 4% of calcium alkylbenzenesulfonate and 35% of methylnaphthalene. Example 5 Wettable powder 40% of compound number (15), 15% of diatomaceous earth, 15% of clay, 25% of white carbon, 2% of sodium dinaphthylmethanedisulfonate and 3% of sodium ligninsulfonate are uniformly mixed and pulverized. Wettable powder. Example 6 Dust A 2% compound number (20), 5% diatomaceous earth and 93% clay were uniformly mixed and pulverized to give a dust. Example 7 Granules Compound No. (29) 5%, lauryl alcohol sulfate sodium salt 2%, lignin sulfonate sodium 5%, carboxymethyl cellulose 2% and clay 86
% Is uniformly mixed and pulverized. 100 parts by weight of this mixture is
The mixture was kneaded by adding parts by weight, processed into granules of 14 to 32 mesh using an extrusion granulator, and then dried to obtain granules. (Effects of the Invention) The 1-phenyltriazole derivative of the present invention has extremely excellent insecticidal activity against planthoppers such as brown planthopper, brown planthopper and brown planthopper, and beetles such as rice weevil and rice beetle, and has extremely excellent systemic insecticidal activity. Have. Hemiptera, such as leafhoppers, aphids, and stink bugs, lepidoptera, such as moths and cutworms, diptera, such as housefly and mosquitoes, Coleoptera, such as azuki beetles and scarab beetles, and straight-winged insects, such as German cockroaches. It is also effective in controlling spider mites such as spider mites and mandarin mites. Next, the effects of the insecticide of the present invention will be described with reference to test examples. Test Example 1 Insecticidal test of brown planthoppers The wettable powder prepared according to Example 5 was diluted with water. Rice stems and leaves were immersed in this solution, air-dried, and allowed to stand in a test tube.
Ten brown planthopper larvae were released into the larvae, and plugged with absorbent cotton. Then, it was placed in a constant temperature room at 25 ° C., and after 6 days, the number of dead insects was examined, and the mortality was calculated. The test was performed in a two-part system. The results are shown in Tables 2 and 3. The same applies to the subsequent tests. Test Example 2 Rice Weevil Insecticidal Test A wettable powder prepared according to Example 5 was used as an active ingredient at 10 ppm.
Diluted with water to a concentration of This solution was placed in a polyethylene cup having a diameter of 90 mm. The adult water weevil in it
We released 10 heads and covered them. After that, put it in a 25 ° C constant temperature room,
Two days later, the number of dead insects was examined, and the mortality was calculated. Test 2
I went in a consolidation. The results are shown in Table 4. Test Example 3 Insect Insecticidal Test A wettable powder prepared according to Example 5 was 500 ppm as an active ingredient.
Diluted with water to a concentration of Cabbage leaves were immersed in this chemical solution, air-dried, and then placed in a 55 mm diameter polyethylene cup. Ten of the third instar larvae of the Japanese moth were released into it and covered. Then, put in a constant temperature room of 25 ℃, three days later to investigate the number of dead insects,
The mortality was calculated. The test was performed in a two-part system. Result 5
It is shown in the table. Test Example 4 Penetrating insecticide of the brown planthopper, a wettable powder prepared according to Example 5 having an active ingredient concentration of 10
Diluted with water to give ppm. This chemical solution was put in a bottle, the root of the rice seedling was immersed in the bottle, the seedling was fixed with a rubber stopper, and a wire mesh cylinder was put thereon. Ten female female larvae of the brown planthopper were placed in it and capped. After that, put it in a 25 ° C constant temperature room,
Two days later, the number of dead insects was examined, and the mortality was calculated. Test 2
I went in a consolidation. The results are shown in Table 6.
フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ０７Ｄ 249/12 ５１１ Ｃ０７Ｄ 249/12 ５１１ 249/14 ５０３ 249/14 ５０３ ５０４ ５０４ ５０５ ５０５ 401/04 ２４９ 401/04 ２４９ 403/04 ２０７ 403/04 ２０７ 405/04 ２４９ 405/04 ２４９ 405/12 ２４９ 405/12 ２４９ 409/04 ２４９ 409/04 ２４９ 409/06 ２４９ 409/06 ２４９ 409/12 ２４９ 409/12 ２４９ (56)参考文献 特開 平１−230562（ＪＰ，Ａ) 特開 平２−91062（ＪＰ，Ａ)Continuation of the front page (51) Int.Cl. 6 Identification code Agency reference number FI Technical display location C07D 249/12 511 C07D 249/12 511 249/14 503 249/14 503 504 504 505 505 505 401/04 249 401 / 04 249 403/04 207 403/04 207 405/04 249 405/04 249 405/12 249 405/12 249 409/04 249 409/04 249 409/06 249 409/06 249 409/12 249 409/12 249 (56) References JP-A-1-230562 (JP, A) JP-A-2-91062 (JP, A)
Claims (2)
し、Ｙはアルコキシ基、アルキルチオ基、アルキルスル
ホニル基、アリルチオ基、ジエチルアミノ基又はアルキ
ル基（該基はハロゲン原子、ジメチルカルバモイル基又
はアルコキシ基で置換されてもよい。）を示し、Ｚはア
ルケニル基、フェニル基（該基はフッ素原子、水酸基又
はメチル基で置換されてもよい。）、 式 （式中、R1とR2は、同一又は相異なり、水素原子、アル
キル基、アルコキシカルボニルメチル基を示す。）で表
される基、 式 ［式中、R3はアルキル基、フリル基、チエニル基又はフ
ェニル基（該基はハロゲン原子又はトリフルオロメチル
基で置換されてもよい。）を示す。］で表される基、１
−ピロリル基、アルケニルオキシ基、ピリジン−２−イ
ル基、エトキシメチリデンアミノ基、チエニルメチル
基、 式 （式中、Ａは酸素原子、硫黄原子又は窒素原子を示し、
R4は水素原子、ハロゲン原子、アルキル基又はニトロ基
を示す。）で表される基、グアニジル基、トリフルオロ
メチル基又はアルキル基を示す。 但し、 （ａ）Ｙが炭素数２〜６のアルキル基を示す場合には、
Ｚはアルケニル基、フェニル基（該基はフッ素原子、水
酸基又はメチル基で置換されている。）、アルコキシカ
ルボニルメチルアミノ基、 式 ［式中、R3はフリル基、チエニル基又はフェニル基（該
基はハロゲン原子又はトリフルオロメチル基で置換され
てもよい。）を示す。］で表される基、アルケニルオキ
シ基、ピリジン−２−イル基、チエニルメチル基、 式 （式中、Ａは酸素原子、硫黄原子又は窒素原子を示し、
R4は水素原子、ハロゲン原子、アルキル基又はニトロ基
を示す。）で表される基、グアニジル基又はアルキル基
を示し、 （ｂ）Ｙがアルコキシ基、アルキルチオ基、アルキルス
ルホニル基、アリルチオ基、ジエチルアミノ基、トリフ
ルオロメチル基、ジメチルカルバモイルアルキル基又は
アルコキシメチル基を示す場合には、Ｚはフェニル基、 式 （式中、R1とR2は、同一又は相異なり、水素原子、アル
キル基を示す。）で表される基、アルキルカルボニルア
ミノ基、１−ピロリル基、エトキシメチリデンアミノ基
又はトリフルオロメチル基を示す。｝で表されるフェニ
ルトリアゾール誘導体。(1) General formula In the formula, X represents a chlorine atom or a trifluoromethyl group, Y represents an alkoxy group, an alkylthio group, an alkylsulfonyl group, an allylthio group, a diethylamino group or an alkyl group (the group is a halogen atom, a dimethylcarbamoyl group or an alkoxy group). Z may be substituted with an alkenyl group, a phenyl group (the group may be substituted with a fluorine atom, a hydroxyl group or a methyl group); (Wherein, R 1 and R 2 are the same or different and each represent a hydrogen atom, an alkyl group, or an alkoxycarbonylmethyl group). [Wherein, R 3 represents an alkyl group, a furyl group, a thienyl group, or a phenyl group (the group may be substituted with a halogen atom or a trifluoromethyl group). A group represented by 1
-A pyrrolyl group, an alkenyloxy group, a pyridin-2-yl group, an ethoxymethylideneamino group, a thienylmethyl group, a formula (Where A represents an oxygen atom, a sulfur atom or a nitrogen atom,
R 4 represents a hydrogen atom, a halogen atom, an alkyl group or a nitro group. ), A guanidyl group, a trifluoromethyl group or an alkyl group. However, when (a) Y represents an alkyl group having 2 to 6 carbon atoms,
Z is an alkenyl group, a phenyl group (the group is substituted with a fluorine atom, a hydroxyl group or a methyl group), an alkoxycarbonylmethylamino group, a formula [In the formula, R 3 represents a furyl group, a thienyl group or a phenyl group (the group may be substituted with a halogen atom or a trifluoromethyl group). A alkenyloxy group, a pyridin-2-yl group, a thienylmethyl group, a group represented by the formula: (Where A represents an oxygen atom, a sulfur atom or a nitrogen atom,
R 4 represents a hydrogen atom, a halogen atom, an alkyl group or a nitro group. ), A guanidyl group or an alkyl group, and (b) Y represents an alkoxy group, an alkylthio group, an alkylsulfonyl group, an allylthio group, a diethylamino group, a trifluoromethyl group, a dimethylcarbamoylalkyl group or an alkoxymethyl group. Where Z is a phenyl group; (Wherein R 1 and R 2 are the same or different and each represent a hydrogen atom or an alkyl group), an alkylcarbonylamino group, a 1-pyrrolyl group, an ethoxymethylideneamino group or a trifluoromethyl Represents a group. A phenyltriazole derivative represented by｝.
し、Ｙはアルコキシ基、アルキルチオ基、アルキルスル
ホニル基、アリルチオ基、ジエチルアミノ基又はアルキ
ル基（該基はハロゲン原子、ジメチルカルバモイル基又
はアルコキシ基で置換されてもよい。）を示し、Ｚはア
ルケニル基、フェニル基（該基はフッ素原子、水酸基又
はメチル基で置換されてもよい。）、 式 （式中、R1とR2は、同一又は相異なり、水素原子、アル
キル基、アルコキシカルボニルメチル基を示す。）で表
される基、 式 ［式中、R3はアルキル基、フリル基、チエニル基又はフ
ェニル基（該基はハロゲン原子又はトリフルオロメチル
基で置換されてもよい。）を示す。］で表される基、１
−ピロリル基、アルケニルオキシ基、ピリジン−２−イ
ル基、エトキシメチリデンアミノ基、チエニルメチル
基、 式 （式中、Ａは酸素原子、硫黄原子又は窒素原子を示し、
R4は水素原子、ハロゲン原子、アルキル基又はニトロ基
を示す。）で表される基、グアニジル基、トリフルオロ
メチル基又はアルキル基を示す。 但し、 （ａ）Ｙが炭素数２〜６のアルキル基を示す場合には、
Ｚはアルケニル基、フェニル基（該基はフッ素原子、水
酸基又はメチル基で置換されている。）、アルコキシカ
ルボニルメチルアミノ基、 式 ［式中、R3はフリル基、チエニル基又はフェニル基（該
基はハロゲン原子又はトリフルオロメチル基で置換され
てもよい。）を示す。］で表される基、アルケニルオキ
シ基、ピリジン−２−イル基、チエニルメチル基、 式 （式中、Ａは酸素原子、硫黄原子又は窒素原子を示し、
R4は水素原子、ハロゲン原子、アルキル基又はニトロ基
を示す。）で表される基、グアニジル基又はアルキル基
を示し、 （ｂ）Ｙがアルコキシ基、アルキルチオ基、アルキルス
ルホニル基、アリルチオ基、ジエチルアミノ基、トリフ
ルオロメチル基、ジメチルカルバモイルアルキル基又は
アルコキシメチル基を示す場合には、Ｚはフェニル基、 式 （式中、R1とR2は、同一又は相異なり、水素原子、アル
キル基を示す。）で表される基、アルキルカルボニルア
ミノ基、１−ピロリル基、エトキシメチリデンアミノ基
又はトリフルオロメチル基を示す。｝で表されるフェニ
ルトリアゾール誘導体を有効成分として含有する殺虫
剤。2. The general formula In the formula, X represents a chlorine atom or a trifluoromethyl group, Y represents an alkoxy group, an alkylthio group, an alkylsulfonyl group, an allylthio group, a diethylamino group or an alkyl group (the group is a halogen atom, a dimethylcarbamoyl group or an alkoxy group). Z may be substituted with an alkenyl group, a phenyl group (the group may be substituted with a fluorine atom, a hydroxyl group or a methyl group); (Wherein, R 1 and R 2 are the same or different and each represent a hydrogen atom, an alkyl group, or an alkoxycarbonylmethyl group). [Wherein, R 3 represents an alkyl group, a furyl group, a thienyl group, or a phenyl group (the group may be substituted with a halogen atom or a trifluoromethyl group). A group represented by 1
-A pyrrolyl group, an alkenyloxy group, a pyridin-2-yl group, an ethoxymethylideneamino group, a thienylmethyl group, a formula (Where A represents an oxygen atom, a sulfur atom or a nitrogen atom,
R 4 represents a hydrogen atom, a halogen atom, an alkyl group or a nitro group. ), A guanidyl group, a trifluoromethyl group or an alkyl group. However, when (a) Y represents an alkyl group having 2 to 6 carbon atoms,
Z is an alkenyl group, a phenyl group (the group is substituted with a fluorine atom, a hydroxyl group or a methyl group), an alkoxycarbonylmethylamino group, a formula [In the formula, R 3 represents a furyl group, a thienyl group or a phenyl group (the group may be substituted with a halogen atom or a trifluoromethyl group). A alkenyloxy group, a pyridin-2-yl group, a thienylmethyl group, a group represented by the formula: (Where A represents an oxygen atom, a sulfur atom or a nitrogen atom,
R 4 represents a hydrogen atom, a halogen atom, an alkyl group or a nitro group. ), A guanidyl group or an alkyl group, and (b) Y represents an alkoxy group, an alkylthio group, an alkylsulfonyl group, an allylthio group, a diethylamino group, a trifluoromethyl group, a dimethylcarbamoylalkyl group or an alkoxymethyl group. Where Z is a phenyl group; (Wherein, R 1 and R 2 are the same or different and each represent a hydrogen atom or an alkyl group), an alkylcarbonylamino group, a 1-pyrrolyl group, an ethoxymethylideneamino group or a trifluoromethyl Represents a group. An insecticide containing a phenyltriazole derivative represented by｝ as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63242881A JP2729810B2 (en) | 1988-09-27 | 1988-09-27 | Phenyltriazole derivatives and insecticides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63242881A JP2729810B2 (en) | 1988-09-27 | 1988-09-27 | Phenyltriazole derivatives and insecticides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0291061A JPH0291061A (en) | 1990-03-30 |
| JP2729810B2 true JP2729810B2 (en) | 1998-03-18 |
Family
ID=17095619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63242881A Expired - Lifetime JP2729810B2 (en) | 1988-09-27 | 1988-09-27 | Phenyltriazole derivatives and insecticides |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2729810B2 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU701981B2 (en) * | 1995-12-21 | 1999-02-11 | Sumitomo Chemical Company, Limited | Triazole derivatives and uses thereof |
| AU8127898A (en) * | 1997-07-11 | 1999-02-08 | Nippon Soda Co., Ltd. | Pyridyltriazole compounds, processes for producing the same and agricultural andhorticultural germicides |
| CO5221041A1 (en) * | 1998-10-23 | 2002-11-28 | Dow Agrosciences Llc | COMPOUNDS OF 3- (REPLACED PHENYL) -5-TIENIL-1.2.4- TRIAZOL WITH ACTIVITY AGAINST WHITE FLY AND INSECTICIATED COMPOSITIONS CONTAINING IT |
| DE69936592T2 (en) * | 1998-10-23 | 2008-04-30 | Dow Agrosciences Llc, Indianapolis | PROCESS FOR PREPARING 3- (SUBSTITUTED PHENYL) -5-THIENYL (OR FURYL) - 1,2,4-TRIAZOLENE AND THE INTERMEDIATES USED IN THE PROCESS |
| KR101310073B1 (en) | 2004-10-20 | 2013-09-24 | 이하라케미칼 고교가부시키가이샤 | 3-triazolylphenyl sulfide derivative and insecticide/acaricide/nematicide containing the same as active ingredient |
| JP5507257B2 (en) * | 2007-11-30 | 2014-05-28 | イハラケミカル工業株式会社 | (1H-1,2,4-triazol-1-yl) aryl compound and method for producing the same |
-
1988
- 1988-09-27 JP JP63242881A patent/JP2729810B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0291061A (en) | 1990-03-30 |
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