JPS63159373A - Pyridazinones and insecticide, acaricide and nematocide - Google Patents
Pyridazinones and insecticide, acaricide and nematocideInfo
- Publication number
- JPS63159373A JPS63159373A JP30639586A JP30639586A JPS63159373A JP S63159373 A JPS63159373 A JP S63159373A JP 30639586 A JP30639586 A JP 30639586A JP 30639586 A JP30639586 A JP 30639586A JP S63159373 A JPS63159373 A JP S63159373A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- formulas
- tables
- formula
- 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
- 239000002917 insecticide Substances 0.000 title claims abstract description 12
- 230000000895 acaricidal effect Effects 0.000 title claims abstract description 10
- 230000001069 nematicidal effect Effects 0.000 title claims abstract description 9
- 239000000642 acaricide Substances 0.000 title claims abstract description 7
- 239000005645 nematicide Substances 0.000 title claims abstract description 7
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 33
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 241001465754 Metazoa Species 0.000 claims abstract description 9
- 241000238876 Acari Species 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 230000003071 parasitic effect Effects 0.000 claims abstract description 7
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
- 125000005495 pyridazyl group Chemical group 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 239000000126 substance Substances 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 11
- -1 pyrazoyl group Chemical group 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 125000005412 pyrazyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 46
- 239000012433 hydrogen halide Substances 0.000 abstract description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract 5
- 150000002367 halogens Chemical class 0.000 abstract 5
- 239000003463 adsorbent Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 241000244206 Nematoda Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 241000607479 Yersinia pestis Species 0.000 description 5
- 230000000749 insecticidal effect Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 230000009969 flowable effect Effects 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000239290 Araneae Species 0.000 description 3
- 241001414720 Cicadellidae Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 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
- 241000488589 Tetranychus kanzawai Species 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- UWMPWJXKRMTVIN-UHFFFAOYSA-N 1-benzylsulfanyl-2-(chloromethyl)benzene Chemical compound ClCC1=CC=CC=C1SCC1=CC=CC=C1 UWMPWJXKRMTVIN-UHFFFAOYSA-N 0.000 description 2
- GLGQMFICPMIOHO-UHFFFAOYSA-N 2-tert-butyl-4-chloro-5-sulfanylpyridazin-3-one Chemical compound CC(C)(C)N1N=CC(S)=C(Cl)C1=O GLGQMFICPMIOHO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 2
- 235000006008 Brassica napus var napus Nutrition 0.000 description 2
- 240000000385 Brassica napus var. napus Species 0.000 description 2
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- 241000255749 Coccinellidae Species 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 241000227653 Lycopersicon Species 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229920006328 Styrofoam Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001408 amides 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
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 238000012746 preparative thin layer chromatography Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000008261 styrofoam Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 241000206761 Bacillariophyta Species 0.000 description 1
- 241000238678 Boophilus Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000482313 Globodera ellingtonae Species 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 210000000436 anus Anatomy 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- 238000009835 boiling Methods 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
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000007689 inspection Methods 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
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- UGJCNRLBGKEGEH-UHFFFAOYSA-N sodium-binding benzofuran isophthalate Chemical compound COC1=CC=2C=C(C=3C(=CC(=CC=3)C(O)=O)C(O)=O)OC=2C=C1N(CCOCC1)CCOCCOCCN1C(C(=CC=1C=2)OC)=CC=1OC=2C1=CC=C(C(O)=O)C=C1C(O)=O UGJCNRLBGKEGEH-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は新規な３（２Ｈ）−ビリダジノンＫＭ ”Ｊ体
および該誘導体を有効成分として含有する農園芸用殺虫
、殺ダニ、殺線虫および動物に寄生するダニの駆除剤に
関するものである。Detailed Description of the Invention [Field of Industrial Application] The present invention provides novel 3(2H)-pyridazinone KM "J form and its derivatives for agricultural and horticultural insecticides, acaricides, nematicides and This relates to an exterminator for mites parasitic on animals.
本発明者らは、先に下記の一般式（Ｉｆ）で表される一
部の３（２Ｈ）−ピリダジノン誘導体が農園芸用殺虫、
殺ダニ、殺線虫、殺菌作用を有することを見出した。（
ヨーロッパ公開特許第００８８３８４号公報、ヨーロッ
パ公開特許第０１３４４３９号公報およびヨーロッパ公
開特許第０１８３２１２号公報参照）〔式中、例えばＲ
′はアルキル基、Ａ′はハロゲン原子１．Ｒ■０および
Ｒ１は水素原子または低級アルキル基、Ｘ′は酸素原子
もしくは硫黄原子、Ｙ′は低級アルキル基、シクロアル
キル基、低級アルコキシ基、低級ハロアルキル基、低級
ハロアルコキシ基、置換フェニル基などを示すゆ〕後記
一般式（１）で表される本発明化合物は、一般式（ＩＩ
）で表される従来技術に包含されない新規化合物であり
、優れた殺虫、殺ダニ、殺線虫作用を有し、農園芸上有
害な生物を有効に防除できることを見出し、本発明を完
成した。この効果については後述する試験例に明示しで
ある。The present inventors previously discovered that some 3(2H)-pyridazinone derivatives represented by the following general formula (If) can be used as agricultural and horticultural insecticides.
It was discovered that it has acaricidal, nematicidal, and bactericidal effects. (
(See European Patent Application No. 0088384, European Publication No. 0134439 and European Publication No. 0183212) [wherein, for example, R
' is an alkyl group, A' is a halogen atom 1. R■0 and R1 are a hydrogen atom or a lower alkyl group, X' is an oxygen atom or a sulfur atom, Y' is a lower alkyl group, a cycloalkyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group, a substituted phenyl group, etc. The compound of the present invention represented by the general formula (1) shown below has the general formula (II
), which is not included in the prior art, has excellent insecticidal, acaricidal, and nematocidal effects, and has been found to be able to effectively control organisms harmful to agriculture and horticulture, and has completed the present invention. This effect will be clearly demonstrated in the test examples described later.
本発明は、一般式〔Ｉ〕 ：
〔式中、Ｒは炭素数１〜６のアルキル基を表し、Ａはハ
ロゲン原子、炭素数１〜４のアルキル基、炭素数１〜４
のアルコキシ基、炭素数１〜４のアルキルチオ基または
水素原子を表し、Ｘは酸素原子または硫黄原子を表し、
Ｒ１およびＲ２は、それぞれ独立に水素原子または炭素
数１〜４のアル３ Ｒ４
キル基を表し、Ｂは、 −Ｃ＝Ｃ−を表し、Ｒ３および
Ｒ４は、それぞれ独立に水素原子または炭素数１〜４の
アルキル基を表し、ｍは０または１を表し、Ｒ６はハロ
ゲン原子、炭素数１〜４のアルキル基、炭素数１〜４の
アルコキシ基、炭素数１〜４のハロアルキル基またはニ
トロ基を表し、Ｒ７・
ｎは０．１〜４の整数を表し、Ｙは一〇Ｃ１１−。The present invention is based on the general formula [I]: [wherein, R represents an alkyl group having 1 to 6 carbon atoms, and A represents a halogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms]
represents an alkoxy group, an alkylthio group having 1 to 4 carbon atoms, or a hydrogen atom, and X represents an oxygen atom or a sulfur atom,
R1 and R2 each independently represent a hydrogen atom or an Al3R4 group having 1 to 4 carbon atoms, B represents -C=C-, and R3 and R4 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ~4 alkyl group, m represents 0 or 1, and R6 is a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or a nitro group. , R7.n represents an integer from 0.1 to 4, and Y is 10C11-.
Ｒ１１ＲａＲａ Ｒ１１Ｒ９−Ｎ−、−５−
ＣＨ−、−ＳＯ２−ＣＩ＋−、−０ＣＲ−Ｃ１１−。R11RaRa R11R9-N-, -5-
CH-, -SO2-CI+-, -0CR-C11-.
Ｒａ Ｒ９
−ＣＬＣＩＩ−、−ＣＨ＝Ｃｌｌ−、−ＣＨＢｒＣＨＢ
ｒ−、−５Ｏｚ−、−０３Ｏｚ−Ｒ１１Ｒ９
または−〇ｃｕ−ｃ−Ｎ−を表し、Ｒ７は水素原子また
は炭素数１〜４のアルキル基を表し、（但し、Ｑがフェ
ニル基のとき水素原子は含まない）ＲａおよびＲ９は水
素原子または炭素数１〜４のアルキル基を表し、Ｑは無
置換もしくは置ｔｌを有するフェニル基、ピリジル基、
ピリダジノン、ピリミジル基、ピラジル基、チェニル基
、フリル基、ピロリル基、ピラゾリル基、イミダゾリル
基、チアゾリル基、オキサシリル基、イソチアゾリル基
、イソオキサシリル基、トリアゾリル基、チアジアゾリ
ル基、オキサジアゾリル基、トリアジル基、ナフチル基
、キノリル基、イソキノリル基、キノキザリル基、イン
ドリル基、ベンズイミダゾリル基、ヘンゾチェニル基、
ベンズオキサシリル基またはベンズデアゾリル基を表し
、置換基としては、ハロゲン原子、炭素数１〜４のアル
キル基、炭素数１〜４のアルコキシ基、炭素数１〜４の
ハロアルキル基、炭素数１〜４のアルキルチオ基、アル
キルスルホニル基またはニトロ基より選ばれる。〕で表
される３（２Ｈ）−ピリダジノン３ｉ Ａ５体ならびに
該誘導体を有効成分として含有する農園芸用殺虫、殺ダ
ニ、殺線虫および動物に寄生するダニの駆除剤に関する
ものである。Ra R9 -CLCII-, -CH=Cll-, -CHBrCHB
r-, -5Oz-, -03Oz-R11R9 or -〇cu-c-N-, R7 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms (however, when Q is a phenyl group, a hydrogen atom ) Ra and R9 represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, Q is an unsubstituted or substituted phenyl group, a pyridyl group,
Pyridazinone, pyrimidyl group, pyrazyl group, chenyl group, furyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, oxacylyl group, isothiazolyl group, isoxasilyl group, triazolyl group, thiadiazolyl group, oxadiazolyl group, triazyl group, naphthyl group group, quinolyl group, isoquinolyl group, quinoxalyl group, indolyl group, benzimidazolyl group, henzochenyl group,
Represents a benzoxasilyl group or a benzdeazolyl group, and substituents include a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, and a haloalkyl group having 1 to 4 carbon atoms. selected from an alkylthio group, an alkylsulfonyl group or a nitro group. The present invention relates to agricultural and horticultural insecticides, acaricides, nematicides, and insecticides for killing mites parasitic on animals, which contain 3(2H)-pyridazinone 3i A5 represented by the following formula and the derivatives thereof as active ingredients.
本発明に包含される化合物としては、具体的には例えば
第１表に示す化合物が挙げられる。但し、第１表に示す
化合物は例示のためのものであって、本発明は、これら
のみに限定されるものではない。〔但し、第１表中、Ｍ
ｅはメチル基を、Ｅｔはエチル基を、Ｐｒはプロピル基
を、Ｂｕはブチル基を、ｔはターシャリ−を、Ｓはセカ
ンダリ−を、ｉはイソを示す。〕
なお、本発明に包含される化合物の中で不斉炭素原子を
有する化合物の場合には、光学活性な化合物の（＋）体
および（−）体も含むものである。Specific examples of the compounds included in the present invention include the compounds shown in Table 1. However, the compounds shown in Table 1 are for illustrative purposes only, and the present invention is not limited thereto. [However, in Table 1, M
e represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, Bu represents a butyl group, t represents a tertiary group, S represents a secondary group, and i represents an iso group. ] Among the compounds included in the present invention, in the case of a compound having an asymmetric carbon atom, the (+) and (-) forms of optically active compounds are also included.
第１表に示す化合物の番号は、後に記載する製造例、製
剤例および試験例において参照される。The compound numbers shown in Table 1 are referred to in the production examples, formulation examples, and test examples described later.
第１表
Ｒ′
Ｎｏ、 ＲＸ Ａ −Ｃ−（Ｂ
）＋＋ （Ｒ”） ｌｌ
Ｙ−Ｑ〔以下、余白〕
第１表中の０１〜Ｑ４Ｂは、次の構造式で表される基で
ある。Table 1 R' No, RX A -C-(B
)++ (R”) ll
Y-Q [Hereinafter, blank space] 01 to Q4B in Table 1 are groups represented by the following structural formula.
Ｍｅ Ｍｅ本発明化合物
は、次の反応式に従って製造できる。MeMeThe compound of the present invention can be produced according to the following reaction formula.
（ＩＩＩ） （１’？）本発明化合物Ｃ
Ｉ）
〔式中、Ｒ，Ｒ’、Ｒ”、Ｒ６，Ａ、Ｂ、Ｙ、Ｑ。(III) (1'?) Compound C of the present invention
I) [wherein R, R', R", R6, A, B, Y, Q.
ｍおよびｎは前記と同じ意味を表し、Ｘｌはハロゲン原
子、−ＯＨまたは一５Ｈを表し、×２はハロゲン原子、
−〇１１または一３Ｒを表す。但し、Ｘｌがハロゲン原
子の場合はＸｌは−０１１または一５ｌ＋を表し、Ｘｌ
が−０１１または−３１１の場合はＸＺはハロゲン原子
を表す。〕
すなわち本発明化合物（１）は、原料のひとつである前
記式〔■〕・で表される３（２Ｈ）−ピリダジノン誘導
体と、もう一方の原料である前記式（ＩＶ）で表される
化合物とをハロゲン化水素吸収剤の存在下で反応に影響
しない溶媒中で反応させることによって製造できる。本
発明において溶媒としては低級アルコール類（例えばメ
タノール、エタノール等）、ケトン類（例えば、アセト
ン、メチルエチルケトン等）、炭化水素類（例えば、ベ
ンゼン、トルエン等）、エーテル類（例えば、イソプロ
ピルエーテル、テトラヒドロフラン、１１４−ジオキサ
ン等）、アミド類 （例えば、Ｎ、Ｎ−ジメチルホルム
アミド、ヘキサメチルホスホリックトリアミド等）、ハ
ロゲン化炭化水素類（例えばジクロロメタン、ジクロロ
エタン等）が使用することができる。また必要に応じて
、これらの溶媒と水との混合溶媒も使用することができ
る。m and n represent the same meanings as above, Xl represents a halogen atom, -OH or -5H, x2 represents a halogen atom,
- Represents 〇11 or -3R. However, when Xl is a halogen atom, Xl represents -011 or -5l+, and Xl
When is -011 or -311, XZ represents a halogen atom. ] That is, the compound (1) of the present invention consists of a 3(2H)-pyridazinone derivative represented by the formula [■], which is one of the raw materials, and a compound represented by the formula (IV), which is the other raw material. can be produced by reacting them in the presence of a hydrogen halide absorbent in a solvent that does not affect the reaction. In the present invention, solvents include lower alcohols (e.g., methanol, ethanol, etc.), ketones (e.g., acetone, methyl ethyl ketone, etc.), hydrocarbons (e.g., benzene, toluene, etc.), ethers (e.g., isopropyl ether, tetrahydrofuran, etc.). 114-dioxane, etc.), amides (for example, N,N-dimethylformamide, hexamethylphosphoric triamide, etc.), and halogenated hydrocarbons (for example, dichloromethane, dichloroethane, etc.) can be used. A mixed solvent of these solvents and water can also be used if necessary.
ハロゲン化水素吸収剤としては、無機塩基（例えば、水
素化ナトリウム、水酸化ナトリウム、水酸化カリウム、
炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム等
）および有機塩基（例えば、ナトリウムメトキサイド、
ナトリウムエトキサイド、Ｆ・リエチルアミン、ピリジ
ン等）を用いることができる。また、必要に応じて、反
応系にテトラアンモニウム塩（例えば、テトラ−ｎ−ブ
チルアンモニウムブロマイド、トリエチルベンジルアン
モニウムクロライド等）を触媒として添加してもよい。Hydrogen halide absorbers include inorganic bases (e.g., sodium hydride, sodium hydroxide, potassium hydroxide,
sodium carbonate, potassium carbonate, sodium bicarbonate, etc.) and organic bases (e.g., sodium methoxide,
sodium ethoxide, F. ethylamine, pyridine, etc.) can be used. Furthermore, if necessary, a tetraammonium salt (eg, tetra-n-butylammonium bromide, triethylbenzylammonium chloride, etc.) may be added to the reaction system as a catalyst.
反応温度としては、室温から、反応に使用する溶媒の沸
点までの範囲をとることができる。The reaction temperature can range from room temperature to the boiling point of the solvent used in the reaction.
原料のモル比は任意に設定できるが、等モルまたは、そ
れに近い比率で反応を行うのが有利である。Although the molar ratio of the raw materials can be set arbitrarily, it is advantageous to carry out the reaction at an equimolar ratio or a ratio close to it.
次に本発明化合物の製造方法について製造例を具体的に
挙げて説明するが、本発明はこれらのみに限定されるも
のではない。Next, the method for producing the compound of the present invention will be explained with specific production examples, but the present invention is not limited to these.
製造Ｍ１
２−ｔ−ブチル−４−クロロ−５−（４−（１−（４−
クロロフェニル）エチルオキシ）ベンジルチオ）−３（
２Ｈ）−ピリダジノンの合成（化合物阻３４）
２−ｔ−ブチル−４−クロロ−５−メルカプト−３（２
Ｈ）−ピリダジノン（２，２ｇ）および４−（１−（４
−クロロフェニル）エチルオキシ〕ベンジルクロライド
（２，８ｇ）をＮ、Ｎ −ジメチルホルムアミド（３０
ｍｘ）に溶解し、無水炭酸カリウム（２，８ｇ）を加え
室温にて１０時間攪拌した。この溶液を水に注ぎベンゼ
ンで抽出し、水洗、無水硫酸ナトリウムで乾燥後、減圧
下で溶媒を留去し、得られた結晶をヘキサンにて再結晶
し、標記目的物（３、Ｏｇ）を得た。融点１４８．８−
１５１．３℃製造炭叢
−２−ｔ−ブチル−４−クロロ−５−（４−（２−フェ
ニルエチルオキシ）ベンジルオキシ〕−３（２Ｈ）−ピ
リダジノンの合成（化合物隘７７）４−（２−フェニル
エチルオキシ）ベンジルアルコール（１，３ｇ）をＮ、
Ｎ−ジメチルホルムアミド（１０ｍｊりに溶解し、５５
％水素化ナトリウム（０，４ｇ）を加えた。１０分後に
２−ｔ−ブチル−４，５−ジクロロ−３（２Ｈ）〜ピリ
ダジノン（１，３ｇ）を加え室温にて一昼夜撹拌した。Production M1 2-t-butyl-4-chloro-5-(4-(1-(4-
Chlorophenyl)ethyloxy)benzylthio)-3(
Synthesis of 2H)-pyridazinone (Compound 34) 2-t-Butyl-4-chloro-5-mercapto-3(2
H)-pyridazinone (2,2 g) and 4-(1-(4
-chlorophenyl)ethyloxy]benzyl chloride (2.8 g) was dissolved in N,N-dimethylformamide (30 g).
mx), anhydrous potassium carbonate (2.8 g) was added, and the mixture was stirred at room temperature for 10 hours. This solution was poured into water, extracted with benzene, washed with water, dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the obtained crystals were recrystallized from hexane to obtain the title object (3, Og). Obtained. Melting point 148.8-
151.3°C Production Coal Bed - Synthesis of 2-t-butyl-4-chloro-5-(4-(2-phenylethyloxy)benzyloxy)-3(2H)-pyridazinone (Compound No. 77) 4-( 2-phenylethyloxy)benzyl alcohol (1.3 g) with N,
N-dimethylformamide (dissolved in 10 mj, 55
% sodium hydride (0.4 g) was added. After 10 minutes, 2-t-butyl-4,5-dichloro-3(2H) to pyridazinone (1.3 g) was added, and the mixture was stirred at room temperature all day and night.
この溶液を水に注ぎベンゼンで抽出し、水洗、無水硫酸
ナトリウムで乾燥後、減圧下で溶媒を留去し、得られた
油状物を分取用薄層クロマトグラフィーで分離、精製し
、標記目的物（０，９ｇ）を得た。This solution was poured into water and extracted with benzene. After washing with water and drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The obtained oil was separated and purified by preparative thin layer chromatography. (0.9 g) was obtained.
油状物
ＮＭＲ（δ値） ： １．５８ （ｓ、９Ｈ） 、２
．８−３．１ （ｍ。Oil NMR (δ value): 1.58 (s, 9H), 2
．． 8-3.1 (m.
２８） 、３．９ −４．２ （ｍ、２Ｈ）、５．
０５ （ｓ、２ｔｌ） 、６．７ −７．３ （
ｍ、９）１）、７．６３ （ｓ、１ｌｌ）壓１目生１
２−ｔ−ブチル−４−クロロ−５−Ｃ２−（ベンジルチ
オ）ベンジルチオ）−３（２Ｈ）−ピリダジノンの合成
（化合物ｍ１８０）
２−ｔ−ブチル−４−クロロ−５−メルカプト−３（２
Ｈ）−ピリダジノン（１，２ｇ）および２−（ベンジル
チオ）ベンジルクロライド（１，３ｇ）をＮ、Ｎ−ジメ
チルホルムアミド（３０ｍ７りに溶解し、無水炭酸カリ
ウム（１，０ｇ）を加え、室温から４０℃の温度で４時
間攪拌した。この溶液を水に注ぎベンゼンで抽出し、水
洗、無水硫酸ナトリウムで乾燥後、減圧下で溶媒を留去
し、得られた油状物（２，５４ｇ）を分取用薄層クロマ
トグラフィー（展開液：ベンゼン／酢酸エチル＝２０／
１ ｖ／ｖ）で分離、精製した。油状の標記目的物（２
，２２ｇ）を得た。28), 3.9 -4.2 (m, 2H), 5.
05 (s, 2tl), 6.7 -7.3 (
m, 9) 1), 7.63 (s, 1ll) 1st grade 1 Synthesis of 2-t-butyl-4-chloro-5-C2-(benzylthio)benzylthio)-3(2H)-pyridazinone (compound m180) 2-t-butyl-4-chloro-5-mercapto-3 (2
H)-Pyridazinone (1,2 g) and 2-(benzylthio)benzyl chloride (1,3 g) were dissolved in N,N-dimethylformamide (30 mL), anhydrous potassium carbonate (1,0 g) was added, and the solution was heated to 40 g from room temperature. The solution was stirred for 4 hours at a temperature of Preparative thin layer chromatography (developing solution: benzene/ethyl acetate = 20/
1 v/v) and purified. Oily title object (2
, 22g) was obtained.
ｎｏ ＝１．６１８２ 、ＮＭＲ（δ値） ： １
．５９ （ｓ、９１１）、４．０２ （ｓ、 ２＋
１）、４．１８ （ｓ、２１１） 、７．１ −７
．３ （ｍ、９ｔｉ）、７．５０ （ｓ、ＬＨ）
ｍ吐土
２−ｔ−ブチル−４−クロロ−５−（２−（ベンジルチ
オ）ヘンシルオキシ）−３（２Ｈ）−ピリダジノンの合
成（化合物Ｎｃｉｌ ７９）２−ｔ−７’チル−４−ク
ロロ−５−ヒドロキシ−３（２Ｈ）−ピリダジノン（１
，１ｇ）および２−（ベンジルチオ）ベンジルクロライ
ド（１，３ｇ）をＮ、Ｎ−ジメチルホルムアミド（３０
ｍｆｆ）に熔解し、無水炭酸カリウム（１，０ｇ）を加
え、１１０−１１５℃に加熱し４時間攪拌した。この溶
液を水に注ぎベンゼンで抽出し、水洗、無水硫酸ナトリ
ウムで乾燥後、減圧下で溶媒を留去し、得られた結晶（
２，１３ｇ）をヘキサンにて再結晶し、標記目的物（１
，７７ｇ）を得た。no = 1.6182, NMR (δ value): 1
．． 59 (s, 911), 4.02 (s, 2+
1), 4.18 (s, 211), 7.1 -7
．． 3 (m, 9ti), 7.50 (s, LH) 79) 2-t-7'thyl-4-chloro-5-hydroxy-3(2H)-pyridazinone (1
, 1 g) and 2-(benzylthio)benzyl chloride (1,3 g) in N,N-dimethylformamide (30
mff), anhydrous potassium carbonate (1.0 g) was added, and the mixture was heated to 110-115°C and stirred for 4 hours. This solution was poured into water, extracted with benzene, washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain crystals (
2.13g) was recrystallized from hexane to obtain the title object (1
, 77g) was obtained.
融点９４．６−９７．１°Ｃ
次に製造例１〜４の方法に準じて製造した化合物の製造
例を第２表に記載した。化合物の番号は第１表に対応す
る。Melting point: 94.6-97.1°C Next, production examples of compounds produced according to the methods of Production Examples 1 to 4 are listed in Table 2. Compound numbers correspond to Table 1.
第 ２ 表
化合物階 融点（’ｃ） 化合物嵐 融点（’Ｃ
）１４ ９４．８−９８．７ １２０ １８１
．１−１８４．４１５ ８８．８−９７．８
１２２ （油状物）１８ （油状物）１２５
１８９ −１９９３３ １４３．４−１４６．７
１５７ １１８．８−１２１．１３４ １４８．
８−１５１．３ １７９ ９４．６−９’７．
１７７（油状物） １８０ （油状物）
７８ １０９．４−１１１．１ １９６ １
６８−１７０９５（油状物） ４００ １
２０−１２４〔以下、余白〕
本発明化合物を農園芸用殺虫、殺ダニ、殺線虫、および
動物に寄生するダニの駆除剤として使用するにあたって
は、一般には適当な担体、例えばクレー、タルク、ベン
トナイト、珪藻上等の固体担体あるいは水、アルコール
類（メタノール、エタノール等）、芳香族炭化水素類（
ベンゼン、トルエン、キシレン等）、塩素化炭化水素類
、エーテル類、ケトン類、エステル類（酢酸エチル等）
、酸アミド類（ジメチルホルムアミド等）などの液体担
体と混用して適用することができ、所望により乳化剤、
分散剤、懸濁剤、浸透剤、展着剤、安定剤などを添加し
、液剤、乳剤、水和剤、粉剤、粒剤、フロワブル割等任
意の剤型にて実用に供することができる。また、必要に
応じて製剤または散布時に他種の除草剤、各種殺虫剤、
殺菌剤、植物生長調節剤、共力剤などと混合施用しても
よい。Table 2 Compound floor Melting point ('c) Compound storm Melting point ('C
)14 94.8-98.7 120 181
．． 1-184.415 88.8-97.8
122 (Oil) 18 (Oil) 125
189 -19933 143.4-146.7
157 118.8-121.134 148.
8-151.3 179 94.6-9'7.
177 (Oil) 180 (Oil)
78 109.4-111.1 196 1
68-17095 (oil) 400 1
20-124 [Hereinafter, margins] When using the compound of the present invention as an agricultural and horticultural insecticide, acaricide, nematocide, and a mite exterminator that parasitizes animals, it is generally carried out using a suitable carrier such as clay, talc, Solid carriers such as bentonite and diatoms, or water, alcohols (methanol, ethanol, etc.), aromatic hydrocarbons (
benzene, toluene, xylene, etc.), chlorinated hydrocarbons, ethers, ketones, esters (ethyl acetate, etc.)
It can be applied by mixing with a liquid carrier such as acid amide (dimethylformamide, etc.), and if desired, an emulsifier,
By adding a dispersing agent, suspending agent, penetrating agent, spreading agent, stabilizer, etc., it can be put to practical use in any desired dosage form such as a liquid, emulsion, wettable powder, powder, granule, or flowable solution. In addition, other herbicides, various insecticides,
It may be applied in combination with fungicides, plant growth regulators, synergists, etc.
本発明化合物の施用薬量は適用場面、施用時期、施用方
法、対象病害虫、栽培作物等により差異はあるが一般に
は有効成分量としてヘクタール当たり０．００５〜５０
ｋｇ程度が適当である。The amount of the compound of the present invention to be applied varies depending on the application situation, application time, application method, target pests, cultivated crops, etc., but in general, the amount of active ingredient is 0.005 to 50 per hectare.
Approximately 1 kg is appropriate.
次に本発明化合物を有効成分とする殺虫、殺ダニ、殺線
虫剤および動物に寄生するダニの駆除剤の製剤例を示す
がこれらのみに鬼定されるものではない。なお、以下の
製剤例において「部」は重量部を意味する。Next, examples of formulations of insecticides, acaricides, nematocides, and agents for killing mites parasitic on animals containing the compound of the present invention as an active ingredient will be shown, but the present invention is not limited to these. In addition, in the following formulation examples, "parts" mean parts by weight.
■肛 乳剤
本発明化合物 −−−−−−−−２０部
キシレン −−−−−−−−５５部Ｎ
、Ｎ−ジメチルホルムアミドー−−−−−−２０部ツル
ポール２６８０ −−−−−−−−− ５部（非
イオン性界面活性剤とアニオン性界面活性剤との混合物
：東邦化学工業Ｇ１商品名）以上を均一に混合して乳剤
とする。使用に際しては上記乳剤を５０〜２００００倍
に希釈して有効成分量かへクタール当たり０．００５〜
５０ｋｇになるように散布する。■Anus Emulsion Compound of the present invention -------20 parts Xylene ---55 parts N
, N-dimethylformamide --- 20 parts Tsurpol 2680 --- 5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industry G1 trade name ) The above are mixed uniformly to form an emulsion. When using, the above emulsion is diluted 50 to 20,000 times and the amount of active ingredient is 0.005 to 0.005 per hectare.
Spread it to a total weight of 50 kg.
１Ｍ桝１ 水和剤
本発明化合物 −−−−−−−−２５部
ジークライトＰＦＰ −〜−−−−−−６６
部（カオリナイトとセリサイトの混合物
；ジークライト工業件荀商品名）
ツルポール５０３９ −−−−−−− ４部（
アニオン性界面゛活性剤
：東邦化学工業０１商品名）
カープレックス＃８０ −−−−−−− ３部（
ホワイトカーボン：塩野義製薬（）局部品名）リグニン
スルホン酸カルシウムー−−−−−−２部以上を均一に
混合粉砕して水和剤とする。1M box 1 Wettable powder Compound of the present invention ------25 parts Sieglite PFP ---66
part (mixture of kaolinite and sericite; Zeeklite Industrial Co., Ltd. trade name) Tsurupol 5039 ------- 4 parts (
Anionic surfactant: Toho Chemical Industry 01 trade name) Carplex #80 ------- 3 parts (
White carbon: Shionogi & Co., Ltd. (part name) Calcium lignin sulfonate --- Two or more parts are uniformly mixed and pulverized to make a wettable powder.
使用に際しては上記水和剤を５０〜２００００倍に希釈
して有効成分量かヘクタール当たり０．００５〜５０ｋ
ｇになるように散布する。When using, dilute the above hydrating agent 50 to 20,000 times to obtain an active ingredient amount of 0.005 to 50 kg per hectare.
Spread it so that it becomes g.
製剤例３ 油 剤
本発明化合物 −−−−−−−−１０部
メチルセルソルブ −−−−−−−−９０部
以上を均一に混合して油剤とする。使用に際して上記油
剤を有効成分量かへクタール当たり０．００５〜５０ｋ
ｇになるように散布する。Formulation Example 3 Oil Agent - 10 parts of the compound of the present invention ------- 90 parts or more of methyl cellosolve -------- 90 parts or more are mixed uniformly to prepare an oil agent. When using the above oil agent, the amount of active ingredient is 0.005-50k per hectare.
Spread it so that it becomes g.
Ｕ訂 粉剤
本発明化合物 −−−−−−−３，０部
カープレックス＃８０ −−−−−−− ０．５
部（ホワイトカーボン：塩野義製薬住荀商品名）クレー
−−−−−−−９５部リン酸ジイ
ソプロピル −−−−−−−１，５部以上を均一
に混合粉砕して粉剤とする。使用に際して上記粉剤を有
効成分量かへクタール当たり０．００５〜５０ｋｇにな
るように散布する。U version Powder Compound of the present invention ------3.0 parts Carplex #80 --------- 0.5
Part (white carbon: Shionogi & Co., Ltd. product name) Clay ----------95 parts Diisopropyl phosphate---1.5 parts or more are uniformly mixed and pulverized to form a powder. When used, the above-mentioned powder is spread at an amount of active ingredient of 0.005 to 50 kg per hectare.
計ｙ 粒剤
本発明化合物 −−−−−−−５部ベン
トナイト −−−−−−−５４部タルク
−−−−−−−４０部リグニ
ンスルホン酸カルシウム−−一−−−−１部以上を均一
に混合粉砕して少量の水を加えて撹拌混合し、押出式造
粒機で造粒し、乾燥して粒剤とする。使用に際して上記
粒剤を有効成分量がへクタール当たり０．００５〜５０
ｋｇになるように散布する。Total y Granules Compound of the present invention ------- 5 parts Bentonite - 54 parts Talc - 40 parts Calcium ligninsulfonate - 1 part or more The mixture is mixed and pulverized uniformly, mixed with a small amount of water, and then granulated using an extrusion granulator and dried to form granules. When using the above granules, the amount of active ingredient is 0.005 to 50 per hectare.
Spread it to make a total of kg.
製泪■鉦 フロアブル剤
本発明化合物 −−−−−−−２５部ツ
ルポール３３５３ −−−−−−− １０部（
非イオン性界面活性剤：東邦化学工業（＋１商品名）ル
ノックス１００ＯＣ−−−−−−−０，５部（陰イオン
界面活性剤：東邦化学工業■商品名）１％ザンサンガム
水溶液 −−−−−−−２０部（天然高分子）
水 −−−−−−−
４４，５部有効成分（本発明化合物）を除く上記の成分
を均一に溶解し、ついで本発明化合物を加えよく攪拌し
た後、サンドミルにて湿式粉砕してフロアブル剤を得る
。使用に際しては、上記フロアブル剤を５０〜２０００
０倍に希釈して有効成分量かヘクタール当たり０．００
５〜５０ｋｇになるように散布する。Flowable agent Compound of the present invention - 25 parts Tsurupol 3353 - 10 parts (
Nonionic surfactant: Toho Chemical Industry (+1 trade name) Lunox 100OC---0.5 parts (anionic surfactant: Toho Chemical Industry ■trade name) 1% xanthan gum aqueous solution ----- ---20 parts (natural polymer) Water ------
44.5 parts The above components except for the active ingredient (the compound of the present invention) are uniformly dissolved, and then the compound of the present invention is added thereto, thoroughly stirred, and then wet-pulverized in a sand mill to obtain a flowable agent. When using, add the above flowable agent to 50 to 2000
The amount of active ingredient when diluted 0 times is 0.00 per hectare.
Spread it to a weight of 5 to 50 kg.
本発明化合物は、ツマグロヨコバイ等の半翅目害虫、コ
ナガ等の鱗翅目害虫、鞘翅目害虫、アカイエカ等の衛生
害虫に卓越した殺虫力を有するとともに、果樹および疏
菜に寄生する種々のダニ、例えば、ナミハダニ、カンザ
ワハダニ、ニセナミハダニ、ミカンハダニ、リンゴハダ
ニ等および動物に寄生するダニ例えば、オウシマダニ、
ブーフィラス・アユュレイタス、アンプリオンマ・マク
レイタム、リビセファラス・アペンディクラークス、フ
タトゲチマダニ等の防除にも有効である。The compounds of the present invention have excellent insecticidal power against Hemiptera pests such as leafhoppers, Lepidoptera pests such as the diamondback moth, Coleoptera pests, and sanitary pests such as Culex mosquito, and also have excellent insecticidal power against various mites that parasitize fruit trees and canola, such as , two-spotted spider mite, Kanzawa spider mite, false two-spotted spider mite, citrus spider mite, apple spider mite, etc., and mites parasitic on animals such as the American spider mite,
It is also effective in controlling Boophilus ayuletus, Amplionma maculatum, Ribicephalus appendiclarcus, and the two-legged tick.
また、果樹および疏菜に寄生する種々のセンチュウ例え
ば、ネコブセンチュウ、ネグサレセンチュウ、シストセ
ンチュウなどの防除にも有効である。It is also effective in controlling various nematodes that parasitize fruit trees and canola, such as the nematode nematode, the nematode nematode, and the cyst nematode.
また、牛、馬、羊、豚などの家畜類、家禽類、および犬
、猫、うさぎなどの動物に寄生するダニの駆除剤として
も優れている。It is also excellent as an exterminator for mites parasitic on livestock such as cows, horses, sheep, and pigs, poultry, and animals such as dogs, cats, and rabbits.
以下の試験例において具体的に説明する。This will be specifically explained in the following test examples.
ｇ± ツマグロヨコバイに対する殺虫試験本発明化合物
を含有する乳剤を水で希釈し、１１０００ｐｐ濃度の薬
液を調整した。この薬液中にイネの茎葉を約１０秒間浸
漬し、この茎葉をガラス円筒に入れ、有機リン系殺虫剤
に抵抗性を有するツマグロヨコバイ成虫１０頭を放ち、
孔のあいたプラスチック製蓋をかぶせた。この円筒を２
５℃の恒温室に収容し、９６時間経過後の死出率を下記
の計算式から求めた。g± Insecticidal test against leafhopper The emulsion containing the compound of the present invention was diluted with water to prepare a chemical solution with a concentration of 11,000 pp. Rice stems and leaves were immersed in this chemical solution for about 10 seconds, placed in a glass cylinder, and 10 adult leafhoppers, which are resistant to organophosphorus insecticides, were released.
A perforated plastic lid was placed on top. This cylinder is 2
The animals were housed in a constant temperature room at 5° C., and the mortality rate after 96 hours was calculated using the following formula.
なお、試験は２区制で行なった。The test was conducted in two sections.
その結果、以下の化合物が１００％の死出率を示した。As a result, the following compounds showed a mortality rate of 100%.
本発明化合物 Ｎｏ、１８ 、Ｎｏ、７７ 、Ｎｏ、７
８、Ｎｏ、１５７
拭襞拠１ ニジュウヤホシテントウに対する接触性殺
虫試験
本発明化合物を含有する乳剤を水で希釈し、１１０００
ｐｐ濃度の薬液を調整した。この薬液中にトマトの葉を
約１０秒間浸漬し、風乾後シャーレに入れ、この中にニ
ジュウヤホシテントウ２令幼虫をシャーレ当たり１０頭
を成虫し、孔のあいた蓋をして２５℃恒温室に収容し、
９６時間経過後の死出率を下記の計算式から求めた。な
お、試験は２区制で行なった。Compounds of the present invention No. 18, No. 77, No. 7
8, No, 157 Wiping base 1 Contact insecticidal test against Japanese lady beetle The emulsion containing the compound of the present invention was diluted with water and 11000
A chemical solution with a pp concentration was adjusted. Tomato leaves were dipped in this chemical solution for about 10 seconds, air-dried, and then placed in a petri dish, in which 10 adult 2nd instar larvae of the Japanese ladybug were placed per petri dish. accommodated in
The mortality rate after 96 hours was calculated from the following formula. The test was conducted in two sections.
その結果、以下の化合物が１００％の死出率を示した。As a result, the following compounds showed a mortality rate of 100%.
本発明化合物 Ｎｏ、１５ 、Ｎｏ、３３ 、Ｎｏ、３
４ 、Ｎｏ、７７Ｎｏ、７８ 、Ｎｏ、１２２、Ｎｏ、
１５７、Ｎｏ、３３２抜駿拠主 カンザワハダニに
対する殺ダニ効力試験
インゲンの葉をリーフパンチを用いて径１．５ｃｍの円
形に切り取り、径７ ｃｔｎのスチロールカップ上ｆ７
） ’１２った濾紙上に置いた。これにカンザワハダニ
幼虫を１集光たり１０頭接種した。接種半日後に本発明
化合物を含有する乳剤を、展着剤を加えた水で希釈して
１１０００ｐｐ？ａ度の薬液を調整した。この薬液をス
チロールカップ当たり２ｍｆｆずつ回転式散布塔を用い
て散布し、９６時間経過後の死出率を下記の計算式から
求めた。なお、試験は２区制で行なった。Compounds of the present invention No. 15, No. 33, No. 3
4, No, 77 No, 78, No, 122, No,
157, No. 332 Extraction base Acaricidal efficacy test against Kanzawa spider mites Cut green bean leaves into circles with a diameter of 1.5 cm using a leaf punch, and place them on a styrofoam cup with a diameter of 7 ctn f7.
) was placed on a 12-year old filter paper. This was inoculated with 10 Kanzawa spider mite larvae per light. Half a day after inoculation, the emulsion containing the compound of the present invention was diluted with water to which a spreading agent was added to give a concentration of 11,000 pp? A drug solution was prepared. This chemical solution was sprayed at a rate of 2 mff per styrene cup using a rotary scattering tower, and the mortality rate after 96 hours was determined from the following formula. The test was conducted in two sections.
その結果、以下の化合物が１００％の死出率を示した。As a result, the following compounds showed a mortality rate of 100%.
本発明化合物 Ｎｏ、１８ 、Ｎｏ、７７ 、Ｎｏ、７
８ 、 Ｎｏ、８７μ３先例〕ユ ネコプセンチュウ
に対する殺線虫効力試験
ネコブセンチュウの汚染土壌を径８ｃｍのスチロールカ
ップ上に入れた。本発明化合物を含有する乳剤を、展着
剤を加えた水で希釈して１１０００ｐｐ Ｑ９度の薬液
を調整した。この薬液をスチロールカップ当たり５０ｍ
ｊ２ずつ土壌に潅注した。４８時間経過後に指標作物の
トマト苗を移植した。移植３０日経過後トマトの根を水
洗して、ネコブの寄生の見取り調査を行った。Compounds of the present invention No. 18, No. 77, No. 7
8, No, 87μ3 Precedent] Nematicidal efficacy test against Nekolobacter nematode Contaminated soil from Nekorokki nematode was placed on a styrene cup with a diameter of 8 cm. An emulsion containing the compound of the present invention was diluted with water to which a spreading agent was added to prepare a 11000 pp Q9 chemical solution. 50m of this chemical solution per styrofoam cup.
The soil was irrigated with 2 ml of water. After 48 hours, tomato seedlings of the indicator crop were transplanted. After 30 days of transplantation, the roots of the tomato plants were washed with water, and an inspection was conducted to determine if they were infested with cathoppers.
なお、試験は２区制で行なった。The test was conducted in two sections.
その結果、以下の化合物は、ネコブがほとんど認められ
ず、強い殺線虫活性を呈することがわかった。As a result, it was found that the following compounds exhibit strong nematicidal activity with almost no cat-eyes observed.
本発明化合物 Ｎｏ、９５Compound of the present invention No. 95
Claims (1)
ロゲン原子、炭素数１〜４のアルキル基、炭素数１〜４
のアルコキシ基、炭素数１〜４のアルキルチオ基または
水素原子を表し、Ｘは酸素原子または硫黄原子を表し、
Ｒ＾１およびＲ＾２は、それぞれ独立に水素原子または
炭素数１〜４のアルキル基を表し、Ｂは、▲数式、化学
式、表等があります▼を表し、Ｒ＾３およびＲ＾４は、
それぞれ独立に水素原子または炭素数１〜４のアルキル
基を表し、ｍは０または１を表し、Ｒ＾６はハロゲン原
子、炭素数１〜４のアルキル基、炭素数１〜４のアルコ
キシ基、炭素数１〜４のハロアルキル基またはニトロ基
を表し、ｎは０，１〜４の整数を表し、Ｙは▲数式、化
学式、表等があります▼、▲数式、化学式、表等があり
ます▼、▲数式、化学式、表等があります▼、▲数式、
化学式、表等があります▼、▲数式、化学式、表等があ
ります▼、 ▲数式、化学式、表等があります▼、−ＣＨ＝ＣＨ−、
−ＣＨＢｒＣＨＢｒ−、−ＳＯ＿２−、−ＯＳＯ＿２−
または▲数式、化学式、表等があります▼を表し、Ｒ＾
７は水素原子または炭素数１〜４のアルキル基を表し、
（但し、Ｑがフェニル基のとき水素原子は含まない）Ｒ
＾８およびＲ＾９は水素原子または炭素数１〜４のアル
キル基を表し、Ｑは無置換もしくは置換基を有するフェ
ニル基、ピリジル基、ピリダジル基、ピリミジル基、ピ
ラジル基、チエニル基、フリル基、ピロリル基、ピラゾ
イル基、イミダゾリル基、チアゾリル基、オキサゾリル
基、イソチアゾリル基、イソオキサゾリル基、トリアゾ
リル基、チアジアゾリル基、オキサジアゾリル基、トリ
アシル基、ナフチル基、キノリル基、イソキノリル基、
キノキザリル基、インドリル基、ベンズイミダゾリル基
、ベンゾチエニル基、ベンズオキサゾリル基またはベン
ズチアゾリル基を表し、置換基としては、ハロゲン原子
、炭素数１〜４のアルキル基、炭素数１〜４のアルコキ
シ基、炭素数１〜４のハロアルキル基、炭素数１〜４の
アルキルチオ基、アルキルスルホニル基またはニトロ基
より選ばれる。〕（２）一般式〔 I 〕： ▲数式、化学式、表等があります▼〔 I 〕 で表される３（２Ｈ）−ピリダジノン誘導体の１種また
は２種以上を有効成分として含有することを特徴とする
農園芸用殺虫、殺ダニ、殺線虫および動物に寄生するダ
ニの駆除剤。 〔式中、Ｒは炭素数１〜６のアルキル基を表し、Ａはハ
ロゲン原子、炭素数１〜４のアルキル基、炭素数１〜４
のアルコキシ基、炭素数１〜４のアルキルチオ基または
水素原子を表し、Ｘは酸素原子または硫黄原子を表し、
Ｒ＾１およびＲ＾２は、それぞれ独立に水素原子または
炭素数１〜４のアルキル基を表し、Ｂは、▲数式、化学
式、表等があります▼を表し、Ｒ＾３およびＲ＾４は、
それぞれ独立に水素原子または炭素数１〜４のアルキル
基を表し、ｍは０または１を表し、Ｒ＾６はハロゲン原
子、炭素数１〜４のアルキル基、炭素数１〜４のアルコ
キシ基、炭素数１〜４のハロアルキル基またはニトロ基
を表し、ｎは０，１〜４の整数を表し、Ｙは▲数式、化
学式、表等があります▼、▲数式、化学式、表等があり
ます▼、▲数式、化学式、表等があります▼、▲数式、
化学式、表等があります▼、▲数式、化学式、表等があ
ります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、▲数式、化学式、表等があります▼
、▲数式、化学式、表等があります▼、▲数式、化学式
、表等があります▼、または▲数式、化学式、表等があ
ります▼を表し、Ｒ＾７は水素原子または炭素数１〜４
のアルキル基を表し、（但し、Ｑがフェニル基のとき水
素原子は含まない）Ｒ＾８およびＲ＾９は水素原子また
は炭素数１〜４のアルキル基を表し、Ｑは無置換もしく
は置換基を有するフェニル基、ピリジル基、ピリダジル
基、ピリミジル基、ピラジル基、チエニル基、フリル基
、ピロリル基、ピラゾリル基、イミダゾリル基、チアゾ
リル基、オキサゾリル基、イソチアゾリル基、イソオキ
サゾリル基、トリアゾリル基、チアジアゾリル基、オキ
サジアゾリル基、トリアシル基、ナフチル基、キノリル
基、イソキノリル基、キノキザリル基、インドリル基、
ベンズイミダゾリル基、ベンゾチエニル基、ベンズオキ
サゾリル基またはベンズチアゾリル基を表し、置換基と
しては、ハロゲン原子、炭素数１〜４のアルキル基、炭
素数１〜４のアルコキシ基、炭素数１〜４のハロアルキ
ル基、炭素数１〜４のアルキルチオ基、アルキルスルホ
ニル基またはニトロ基より選ばれる。〕(1) General formula [I]: ▲There are mathematical formulas, chemical formulas, tables, etc.▼3(2H)-pyridazinone derivatives represented by [I]. [In the formula, R represents an alkyl group having 1 to 6 carbon atoms, and A is a halogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms.
represents an alkoxy group, an alkylthio group having 1 to 4 carbon atoms, or a hydrogen atom, and X represents an oxygen atom or a sulfur atom,
R^1 and R^2 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, B represents ▲There are numerical formulas, chemical formulas, tables, etc.▼, and R^3 and R^4 are ,
Each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, m represents 0 or 1, R^6 is a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, Represents a haloalkyl group or nitro group with 1 to 4 carbon atoms, n represents an integer of 0, 1 to 4, and Y represents ▲a mathematical formula, a chemical formula, a table, etc.▼, ▲a mathematical formula, a chemical formula, a table, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas,
There are chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, -CH=CH-,
-CHBrCHBr-, -SO_2-, -OSO_2-
Or ▲ represents a mathematical formula, chemical formula, table, etc. ▼, R^
7 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,
(However, when Q is a phenyl group, it does not contain a hydrogen atom)R
^8 and R^9 represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and Q is an unsubstituted or substituted phenyl group, pyridyl group, pyridazyl group, pyrimidyl group, pyrazyl group, thienyl group, furyl group , pyrrolyl group, pyrazoyl group, imidazolyl group, thiazolyl group, oxazolyl group, isothiazolyl group, isoxazolyl group, triazolyl group, thiadiazolyl group, oxadiazolyl group, triacyl group, naphthyl group, quinolyl group, isoquinolyl group,
It represents a quinoxalyl group, an indolyl group, a benzimidazolyl group, a benzothienyl group, a benzoxazolyl group, or a benzthiazolyl group, and the substituents include a halogen atom, an alkyl group having 1 to 4 carbon atoms, and an alkoxy group having 1 to 4 carbon atoms. , a haloalkyl group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, an alkylsulfonyl group, or a nitro group. ] (2) General formula [I]: ▲There are mathematical formulas, chemical formulas, tables, etc.▼It is characterized by containing one or more types of 3(2H)-pyridazinone derivatives represented by [I] as an active ingredient. Agricultural and horticultural insecticides, acaricides, nematocides, and insecticides for mites parasitic on animals. [In the formula, R represents an alkyl group having 1 to 6 carbon atoms, and A is a halogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms.
represents an alkoxy group, an alkylthio group having 1 to 4 carbon atoms, or a hydrogen atom, and X represents an oxygen atom or a sulfur atom,
R^1 and R^2 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, B represents ▲There are numerical formulas, chemical formulas, tables, etc.▼, and R^3 and R^4 are ,
Each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, m represents 0 or 1, R^6 is a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, Represents a haloalkyl group or nitro group with 1 to 4 carbon atoms, n represents an integer of 0, 1 to 4, and Y represents ▲a mathematical formula, a chemical formula, a table, etc.▼, ▲a mathematical formula, a chemical formula, a table, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas,
There are chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, where R^7 is a hydrogen atom or a carbon number of 1 to 4
represents an alkyl group (however, when Q is a phenyl group, it does not contain a hydrogen atom), R^8 and R^9 represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and Q is an unsubstituted or substituted group. phenyl group, pyridyl group, pyridazyl group, pyrimidyl group, pyrazyl group, thienyl group, furyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, oxazolyl group, isothiazolyl group, isoxazolyl group, triazolyl group, thiadiazolyl group, Oxadiazolyl group, triacyl group, naphthyl group, quinolyl group, isoquinolyl group, quinoxalyl group, indolyl group,
Represents a benzimidazolyl group, benzothienyl group, benzoxazolyl group, or benzthiazolyl group, and substituents include a halogen atom, a C1-4 alkyl group, a C1-4 alkoxy group, and a C1-4 alkoxy group. is selected from a haloalkyl group, an alkylthio group having 1 to 4 carbon atoms, an alkylsulfonyl group, or a nitro group. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30639586A JPS63159373A (en) | 1986-12-24 | 1986-12-24 | Pyridazinones and insecticide, acaricide and nematocide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30639586A JPS63159373A (en) | 1986-12-24 | 1986-12-24 | Pyridazinones and insecticide, acaricide and nematocide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63159373A true JPS63159373A (en) | 1988-07-02 |
Family
ID=17956499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP30639586A Pending JPS63159373A (en) | 1986-12-24 | 1986-12-24 | Pyridazinones and insecticide, acaricide and nematocide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63159373A (en) |
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| WO2018072736A1 (en) * | 2016-10-20 | 2018-04-26 | 沈阳中化农药化工研发有限公司 | Pyridazinone compound and application thereof |
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-
1986
- 1986-12-24 JP JP30639586A patent/JPS63159373A/en active Pending
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|---|---|---|---|---|
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| JP2004123732A (en) * | 2002-09-10 | 2004-04-22 | Takeda Chem Ind Ltd | Five-membered heterocyclic compound |
| US7368578B2 (en) | 2002-09-10 | 2008-05-06 | Takeda Pharmaceutical Company Limited | Five-membered heterocyclic compounds |
| WO2004024705A1 (en) * | 2002-09-10 | 2004-03-25 | Takeda Pharmaceutical Company Limited | Five-membered heterocyclic compounds |
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| US9408927B2 (en) | 2008-02-29 | 2016-08-09 | Lantheus Medical Imaging, Inc. | Contrast agents for applications including perfusion imaging |
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| US9598399B2 (en) | 2012-08-24 | 2017-03-21 | Hamamatsu Photonics K.K. | Compound suitable for detection of mitochondrial complex-1 |
| JPWO2014030709A1 (en) * | 2012-08-24 | 2016-07-28 | 浜松ホトニクス株式会社 | Compounds suitable for detection of mitochondrial Complex-1 |
| WO2014030709A1 (en) * | 2012-08-24 | 2014-02-27 | 浜松ホトニクス株式会社 | Compound suitable for detection of mitochondrial complex-1 |
| WO2018072736A1 (en) * | 2016-10-20 | 2018-04-26 | 沈阳中化农药化工研发有限公司 | Pyridazinone compound and application thereof |
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