JPS63159372A - Pyridazinone compound and insecticide, acaricide and nematocide - Google Patents
Pyridazinone compound and insecticide, acaricide and nematocideInfo
- Publication number
- JPS63159372A JPS63159372A JP30639486A JP30639486A JPS63159372A JP S63159372 A JPS63159372 A JP S63159372A JP 30639486 A JP30639486 A JP 30639486A JP 30639486 A JP30639486 A JP 30639486A JP S63159372 A JPS63159372 A JP S63159372A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- tables
- formulas
- chemical formulas
- 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
- 230000000895 acaricidal effect Effects 0.000 title claims abstract description 10
- 239000002917 insecticide Substances 0.000 title claims abstract description 9
- 239000000642 acaricide Substances 0.000 title claims abstract description 7
- 230000001069 nematicidal effect Effects 0.000 title claims abstract description 7
- 239000005645 nematicide Substances 0.000 title claims abstract description 7
- -1 Pyridazinone compound Chemical class 0.000 title description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 28
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 241001465754 Metazoa Species 0.000 claims abstract description 9
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 8
- 241000238876 Acari Species 0.000 claims abstract description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
- 230000003071 parasitic effect Effects 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 59
- 239000000126 substance Substances 0.000 claims description 49
- 239000004480 active ingredient Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 51
- 239000012433 hydrogen halide Substances 0.000 abstract description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 239000002250 absorbent Substances 0.000 abstract description 2
- 230000002745 absorbent Effects 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 3
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 230000000749 insecticidal effect Effects 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 241000244206 Nematoda Species 0.000 description 5
- 241000607479 Yersinia pestis Species 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 230000009969 flowable effect Effects 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000488589 Tetranychus kanzawai Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000005871 repellent Substances 0.000 description 3
- 230000002940 repellent Effects 0.000 description 3
- 238000003892 spreading Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241001414720 Cicadellidae Species 0.000 description 2
- 241000255749 Coccinellidae Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 240000003768 Solanum lycopersicum Species 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
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals 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
- 239000004927 clay Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000012746 preparative thin layer chromatography Methods 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000004563 wettable powder Substances 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- QMRGPNHBBFGADA-UHFFFAOYSA-N 2-tert-butyl-4-chloro-5-ethoxypyridazin-3-one Chemical compound CCOC=1C=NN(C(C)(C)C)C(=O)C=1Cl QMRGPNHBBFGADA-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000238678 Boophilus Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 240000000385 Brassica napus var. napus Species 0.000 description 1
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 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
- 241000336797 Eoeurysa flavocapitata Species 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
- 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010041235 Snoring Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920006328 Styrofoam Polymers 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 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
- 230000015572 biosynthetic process Effects 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
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002552 dosage form Substances 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
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 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
- 238000001914 filtration Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000011521 glass Substances 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
- 239000004615 ingredient Substances 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
- CYPPCCJJKNISFK-UHFFFAOYSA-J kaolinite Chemical compound [OH-].[OH-].[OH-].[OH-].[Al+3].[Al+3].[O-][Si](=O)O[Si]([O-])=O CYPPCCJJKNISFK-UHFFFAOYSA-J 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium 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
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 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
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008261 styrofoam Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 235000013311 vegetables Nutrition 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）−ピリダジノン誘導体および
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 derivatives and insecticides for agricultural and horticultural use, acaricides, nematicides and parasitic animals containing the derivatives as active ingredients. This relates to a tick repellent.
本発明者らは、先に下記の一般式〔■〕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、Ｒ９およびＲ１０
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。〕後記一般
式（１）で表される本発明化合物は、一般式（Ｉｔ）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 [■] have insecticidal, acaricidal, nematicidal, and bactericidal effects for agricultural and horticultural purposes. . (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, R9 and R10
represents a hydrogen atom or a lower alkyl group, X' represents an oxygen atom or a sulfur atom, Y' represents 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) described below is a novel compound not included in the prior art represented by the general formula (It), and has excellent insecticidal, acaricidal, and nematocidal effects, The present invention was completed based on the discovery that organisms harmful to agriculture and horticulture can be effectively controlled. 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、Ｘおよ
びＤは、それぞれ独立に酸素原子または硫黄原子を表し
、Ａは炭素数１〜４のアルコキシ基、炭素数１〜４のハ
ロアルコキシ基、炭素数１〜４のアルキルチオ基、炭素
数１〜４のハロアルキルチオ基、アルコキシメチルチオ
基、Ｓ１１基またはそれぞれ独立に水素原子または炭素
数１〜４のＲ：ｌ Ｒ４
アルキル基を表し、Ｂは −〇−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、ン原子、炭素数１〜６のアルキル
基、炭素数３〜６のシクロアルキル基、炭素数２〜６の
アルケニル基、炭素数３〜６のシクロアルコキシ基、炭
素数１〜６のアルコキシ基、炭素数１〜６のアルキルチ
オ基、アルキルスルホニル基、炭素数１〜４のハロアル
キル基、ハロアルコキシ基、ハロアルキルチオ基、炭素
数２〜４のアルケニルオキシ基、炭素数１〜４のアルコ
キシカルボニル基、トリメチルシリル基、ジメチルアミ
ノ基、ニトロ基、シ子、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、Ｒ６およびＲ７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、Ｒ８は炭素数１〜４のアルキル基を表し、ｎは０，
１〜３の整数を表し、ｌは０．１〜４の整数を表す。〕
で表される３（２Ｈ）−ピリダジノン誘導体ならびに該
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。The present invention is based on the general formula [I]: (1) [wherein R represents an alkyl group having 1 to 6 carbon atoms, X and D each independently represent an oxygen atom or a sulfur atom, and A represents an alkyl group having 1 to 6 carbon atoms; 4 alkoxy group, a haloalkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, a haloalkylthio group having 1 to 4 carbon atoms, an alkoxymethylthio group, an S11 group, or each independently a hydrogen atom or a carbon number 1 -4 R: l R4 represents an alkyl group, B represents -〇-C-, R3 and R4 are each independently a hydrogen atom or a carbon number of 1 to 4
represents an alkyl group having an atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a cycloalkoxy group having 3 to 6 carbon atoms, and a cycloalkyl group having 1 to 6 carbon atoms. -6 alkoxy group, alkylthio group having 1 to 6 carbon atoms, alkylsulfonyl group, haloalkyl group having 1 to 4 carbon atoms, haloalkoxy group, haloalkylthio group, alkenyloxy group having 2 to 4 carbon atoms, alkenyloxy group having 1 to 4 carbon atoms 4 represents an alkoxycarbonyl group, a trimethylsilyl group, a dimethylamino group, a nitro group, a cylindrical group, 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. , R6 and R7 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R8 represents an alkyl group having 1 to 4 carbon atoms, and n is 0,
It represents an integer of 1 to 3, and l represents an integer of 0.1 to 4. ] The present invention relates to a 3(2H)-pyridazinone derivative represented by the following and an insecticide for agricultural and horticultural use, acaricide, nematicide, and a repellent for mites parasitic on animals, which contain the derivative as an active ingredient.
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表および第２表に示す化合物が挙げられる。但し、
第１表および第２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表および第２表中、Ｍｅはメチル基を
、εｔ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、Ｃはシクロを示す。〕
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 Tables 1 and 2. however,
The compounds shown in Tables 1 and 2 are for illustrative purposes only, and the present invention is not limited thereto. [However, in Tables 1 and 2, Me represents a methyl group, εt represents an ethyl group, Pr represents a propyl group, Bu represents a butyl group, t represents a tertiary group, S represents a secondary, i
represents iso and C represents cyclo. ] 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表および第２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 Tables 1 and 2 are referred to in the production examples, formulation examples, and test examples described later.
第１表
Ｎｏ、ＲＤＡＸ−Ｃ−（Ｂ）！ＩＩ−Ｙｎ「
第２表
ｎ
Ｎｏ、ＲＤ ＾ Ｘ−Ｃ−（Ｉｔ）ｍ−ロに２
第１表および第２表中のＱｌ〜０４６は、次の構造式で
表される基である。Table 1 No. RDAX-C-(B)! II-Yn "Table 2 n No, RD ^
Ｉ
〔以下、余白〕
本発明化合物は、次の（反応式Ａ）または（反応式Ｂ）
に従って製造できる。I [Hereinafter, blank space] The compound of the present invention has the following (reaction formula A) or (reaction formula B)
can be manufactured according to
（反応式Ａ）
（ＩＩＩ） （■）
（反応式Ｂ）
〔式中、Ｒ，Ｒ’ 、 Ｒ２，Ａ、 Ｂ、 Ｄ、 Ｑお
よびｍは前記と同じ意味を表し、×１はハロゲン原子、
−０１１または一５Ｈを表し、Ｘ２はハロゲン原子、−
ＯＨまたは−５１１を表し、Ｘ３はハロゲン原子を表し
、Ｍはアルカリ金属またはアルカリ土類金属を表す。但
し、×１がハロゲン原子の場合はＸ２は−ＯＨまたバー
Ｓｌ＋を表し、Ｘ ” カーＯＨマｋ バー５Ｈ（７）
場合はＸ２はハロゲン原子を表す。〕
（反応式Ａ）に従って、本発明化合物（１）は、原料の
ひとつである前記式（Ｉ［ｌ）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、
１．４−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。(Reaction formula A) (III) (■) (Reaction formula B) [In the formula, R, R', R2, A, B, D, Q and m represent the same meanings as above, ×1 is a halogen atom,
-011 or -5H, X2 is a halogen atom, -
It represents OH or -511, X3 represents a halogen atom, and M represents an alkali metal or an alkaline earth metal. However, if ×1 is a halogen atom, X2 represents -OH or Sl+, and
In this case, X2 represents a halogen atom. ] According to (reaction formula A), the compound (1) of the present invention can be obtained from 3(2H)- represented by the above formula (I[l), which is one of the raw materials.
A pyridazinone derivative and the other raw material, the formula (
It can be produced by reacting the compound represented by IV) 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 (for example, methanol, ethanol, etc.), ketones (for example, acetone, methyl ethyl ketone, etc.), hydrocarbons (for example, benzene, toluene, etc.), ethers (for example,
For example, isopropyl ether, tetrahydrofuran,
1,4-dioxane, etc.), amides (e.g., N, N-
Dimethylformamide, hexamethylphosphoric triamide, etc.), halogenated hydrocarbons (eg, 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、炭酸水素すＩ−ＩＪ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、トリエチルアミン、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
。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。Hydrogen halide absorbers include inorganic bases (e.g., sodium hydride, sodium hydroxide, potassium hydroxide,
sodium carbonate, potassium carbonate, hydrogen carbonate, etc.) and organic bases (eg, sodium methoxide, sodium ethoxide, triethylamine, pyridine, etc.) can be used. Also, if necessary,
A tetraammonium salt (e.g., tetra-n-
butylammonium bromide, triethylbenzylammonium chloride, etc.) may be added as a catalyst. 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.
また（反応式Ｂ）に従って、本発明化合物（１）は、原
料のひとつである前記式（Ｖ）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（
Ｖｌ）で表される金属塩、金属化合物とを反応に影響し
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前記炭化水素類、エーテル類、
ハロゲン化炭化水素類が使用することができる。アルカ
リ金属またはアルカリ土類金属として、リチウム、ナト
リウム、カリウム、マグネシウムなどが使用することが
できる。Further, according to (reaction formula B), the compound (1) of the present invention is one of the raw materials, 3(2H)-
A pyridazinone derivative and the other raw material, the formula (
It can be produced by reacting a metal salt or metal compound represented by Vl) in a solvent that does not affect the reaction. In the present invention, the solvents include the above-mentioned hydrocarbons, ethers,
Halogenated hydrocarbons can be used. Lithium, sodium, potassium, magnesium, etc. can be used as alkali metals or alkaline earth metals.
次に本発明化合物の製造方法について製造例および参考
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 and reference examples, but the present invention is not limited to these.
蒼λ炭上
２−ｔ−ブチル−４−メトキシ−５−ヒドロキシ−３（
２Ｈ）−ピリダジノンの合成
２−ｔ−ブチル−４−クロロ−５−エトキシ−３（２Ｈ
）−ピリダジノンとナトリウムメトキシドをトルエン溶
媒で加熱還流して合成した２−を−ブチル−４−メトキ
シ−５−エトキシ−３（２Ｈ）−ピリダジノン（ｂｐ１
０７−１０９℃１０．５ｍｍｌ１ｇ）（１０ｇ） 、Ｋ
ＯＩＩ （６，２ｇ） 、Ｅｔｏｌｌ （２２ｍｆｆ
１）と水（２２ｍ／）を混合し１８時間還流した。加熱
終了後、ＥｔＯＨを留去し、残渣をベンゼンで抽出し、
水層と分離した。ヘンゼン層からは原料ピリダシノン（
６，８ｇ）が回収された。水層を塩酸で酸性化すると白
色沈澱が生成し、濾取後Ｅ ｔＯＨ−水より再結晶する
と標記目的物の白色結晶（５００ｍｇ）を得た。融点：
１９２．９−１９７．２℃製遺±１
２−ｔ−ブチル−４−メトキシ−５−（４−を−ブチル
ベンジルオキシ）−３（２Ｈ）−ピリダジノンの製造（
化合物１１ｈ９３）
参考例１で合成した２−ｔ−ブチル−４−メトキシ−５
−ヒドロキシ−３（２Ｈ）−ピリダジノ：／ （０，６
ｇ） 、４− ｔ−７’チルベンジルクロライド（０，
７８ｇ）、無水炭酸カリウム（０，６ｇ）およびＮ、Ｎ
−ジメチルホルムアミド（７ｍＡ’）の混合物を攪拌し
ながら加熱した＜１００−１１５℃）。2-t-butyl-4-methoxy-5-hydroxy-3(
Synthesis of 2H)-pyridazinone 2-t-butyl-4-chloro-5-ethoxy-3(2H)-pyridazinone
)-pyridazinone and sodium methoxide were heated under reflux in a toluene solvent to synthesize 2--butyl-4-methoxy-5-ethoxy-3(2H)-pyridazinone (bp1
07-109℃10.5mmml1g) (10g), K
OII (6.2g), Etoll (22mff
1) and water (22 m/) were mixed and refluxed for 18 hours. After heating, EtOH was distilled off and the residue was extracted with benzene.
The aqueous layer was separated. The raw material pyridacinone (
6.8 g) was recovered. When the aqueous layer was acidified with hydrochloric acid, a white precipitate was formed, which was collected by filtration and recrystallized from EtOH-water to obtain white crystals (500 mg) of the title target compound. Melting point:
Preparation of 2-t-butyl-4-methoxy-5-(4-butylbenzyloxy)-3(2H)-pyridazinone (192.9-197.2°C)
Compound 11h93) 2-t-butyl-4-methoxy-5 synthesized in Reference Example 1
-Hydroxy-3(2H)-pyridazino: / (0,6
g), 4-t-7' thylbenzyl chloride (0,
78g), anhydrous potassium carbonate (0,6g) and N,N
-dimethylformamide (7 mA') was heated with stirring (<100-115°C).
４時間加熱した後、水を加えベンゼンで抽出し、水洗、
乾燥後ベンゼンを留去した。得られた油状物をカラムク
ロマトグラフィー（留出液：ベンゼン／酢酸エチル＝
２０／ １ ｖ／ｖ）にて精製し、標記目的物の油状
物（７５０■）を得た。After heating for 4 hours, add water, extract with benzene, wash with water,
After drying, benzene was distilled off. The obtained oil was subjected to column chromatography (distillate: benzene/ethyl acetate =
20/1 v/v) to obtain an oily substance (750 ml) of the title target product.
ＮＭＲ（ＣＤ １３）δ値： １．３２ （ｓ、９１１
） 、１．６１ （ｓ、９１１）、３．９９ （ｓ、
３！Ｉ） 、５．３０ （ｓ、２Ｈ） 、７．４
４ （ｓ、４Ｈ） 、７．６８（ｓ、 ＩＨ）
裂１１１１
２−ｔ−ブチル−４−メトキシ−５−（４−ｎ−ブチル
ベンジルチオ）−３（２Ｈ）−ピリダジノンの製造（化
合物患９２）
２−ｔ−ブチル−４−クロロ−５−（４−ｎ−ブチルベ
ンジルチオ）−３（２Ｈ）−ピリダジノン（１，７２ｇ
）、ナトリウムメトキシド （０，３３ｇ） −トルエ
ン（１０ｍＪ）の混合物を還流温度で１．５時間加熱し
た。放冷後ベンゼンを加え、水洗、乾燥後、有機抽出溶
媒を留去した。油状粗生成物を分取用薄層クロマトグラ
フィーで精製し、標記目的物の赤褐色油状物（１，２２
ｇ）を得た。NMR (CD 13) δ value: 1.32 (s, 911
), 1.61 (s, 911), 3.99 (s,
3! I), 5.30 (s, 2H), 7.4
4 (s, 4H), 7.68 (s, IH) 1111 Production of 2-t-butyl-4-methoxy-5-(4-n-butylbenzylthio)-3(2H)-pyridazinone (compound patient 92) 2-t-Butyl-4-chloro-5-(4-n-butylbenzylthio)-3(2H)-pyridazinone (1,72g
), sodium methoxide (0.33 g) - toluene (10 mJ) was heated at reflux temperature for 1.5 hours. After cooling, benzene was added, and after washing with water and drying, the organic extraction solvent was distilled off. The oily crude product was purified by preparative thin layer chromatography to obtain the title object as a reddish brown oil (1,22
g) was obtained.
ＮＭＲ（ＣＤ Ｉ 、）δ値：ｏ、ａ−１．７軸、７Ｈ
）、１．６０（ｓ、 ９Ｈ） 、２．４ ２．７ （ｍ
、２１１Ｌ ４．０５ （ｓ、５１１）、７．１５ （
ｂｓ、４）１）、７．５５ （ｓ、１）１）袈遺桝ユ
２−ｔ−ブチル−４−ｉ−プロポキシ−５−（４−ｔ−
ブチルベンジルチオ”）−３（２Ｈ）−ピリダジノンの
製造（化合物Ｎｎ２３２）イソプロパツール（１０ｍｊ
りと金属ナトリウム（０，２８ｇ）より８周整したナト
リウムイソプロポキシド、２−ｔ−ブチル−４−クロロ
−５−（４−１−ブチルベンジルチオ）−３（２Ｈ）−
ピリダジノン（３，６５ｇ）およびトルエン（２０ｍｆ
ｆｉ）の混合物を１時間加熱還流した。製造例２と同様
の後処理方法によって標記目的物の白色結晶（３、Ｏｇ
）を得た。NMR (CD I,) δ value: o, a-1.7 axis, 7H
), 1.60 (s, 9H), 2.4 2.7 (m
, 211L 4.05 (s, 511), 7.15 (
bs, 4) 1), 7.55 (s, 1) 1) Keiyu 2-t-butyl-4-i-propoxy-5-(4-t-
Production of butylbenzylthio”)-3(2H)-pyridazinone (compound Nn232) Isopropanol (10mj
Sodium isopropoxide, 2-t-butyl-4-chloro-5-(4-1-butylbenzylthio)-3(2H)-
Pyridazinone (3,65g) and toluene (20mf
The mixture of fi) was heated under reflux for 1 hour. By the same post-treatment method as in Production Example 2, white crystals (3, Og
) was obtained.
融点：８３．５−８６．０℃
製造例４
２−エチル−４−メルカプト−５−（４−ｔ−ブチルベ
ンジルチオ）−３（２Ｈ）−ピリダジノンチオンの製造
（化合物！ＩｋＬ２５２）２−エチル−４−クロロ−５
−（４−ｔ−ブチルベンジルチオ）−３（２Ｈ）−ピリ
ダジノン（１，６８ｇ）、ローソン試薬〔２，４−ビス
（４−メトキシフェニル）−１３−ジチア−２，４−ジ
フォスフエタンー２，４−ジスルフィド］ （１，１
１ｇ）、トルエン（１０ｍ７りの混合物を加熱還流下８
時間撹拌した。減圧上溶媒を留去し、カラムクロマトグ
ラフィー（シリカゲル；留出液：ベンゼン／ヘキサン−
４／ｌｖ／ν）にて分離、精製し、ベンゼン−ヘキサン
混合溶媒にて再結晶しさらに純化した。標記目的物の淡
黄色結晶（０，３ｇ）を得た。Melting point: 83.5-86.0°C Production Example 4 Production of 2-ethyl-4-mercapto-5-(4-t-butylbenzylthio)-3(2H)-pyridazinonethione (compound! IkL252) 2 -ethyl-4-chloro-5
-(4-t-butylbenzylthio)-3(2H)-pyridazinone (1,68 g), Lawson's reagent [2,4-bis(4-methoxyphenyl)-13-dithia-2,4-diphosphethane] 2,4-disulfide] (1,1
1g), toluene (10ml) under reflux.
Stir for hours. The solvent was distilled off under reduced pressure, and column chromatography (silica gel; distillate: benzene/hexane)
4/lv/v) and was further purified by recrystallization from a benzene-hexane mixed solvent. Pale yellow crystals (0.3 g) of the title target product were obtained.
融点：１４２．０−１４４．０℃
製造桝立
２−ｔ−ブチル−４−メルカプト−５−（４＝ｔ−ブチ
ルベンジルチオ）−３（２！Ｉ）−ピリダジノンの製造
（化合物隘２５１）
２−ｔ−ブチル−４−クロロ−５−（４−ｔ−ブチルベ
ンジルチオ）−３（２Ｈ）−ピリダジノン（７，６ｇ）
、７０％Ｎａ５Ｈ（５，６ｇ） 、エタノール（１４０
…１）および水（４ｍｌ）の混合物を６時間加熱還流し
た。エタノール留去後、酢酸エチル、希塩酸水を加え分
液し、酢酸エチル層を分離し、水洗、乾燥後、留去した
。得られた粗結晶物をエタノールから再結晶し標記目的
物の結晶（４，４ｇ）を得た。Melting point: 142.0-144.0°C Production box Production of 2-t-butyl-4-mercapto-5-(4=t-butylbenzylthio)-3(2!I)-pyridazinone (compound 251) 2-t-butyl-4-chloro-5-(4-t-butylbenzylthio)-3(2H)-pyridazinone (7.6 g)
, 70% Na5H (5.6 g), ethanol (140
...1) and water (4 ml) was heated under reflux for 6 hours. After ethanol was distilled off, ethyl acetate and diluted hydrochloric acid were added to separate the layers, and the ethyl acetate layer was separated, washed with water, dried, and then distilled off. The obtained crude crystals were recrystallized from ethanol to obtain crystals (4.4 g) of the title object.
融点：８９−９１’Ｃ
濯ｎ壓ｊ
２−ｔ−ブチル−４−（メトキシメチルチオ）−５−（
４−ｔ−ブチルベンジルチオ）−３（２Ｈ）−ピリダジ
ノンの製造（化合物１ｔ２６１）製造例５で合成した４
−メルカプト体（１，５ｇ ）、クロロメチルメチルエ
ーテル（０，３７ｇ）をＮ、Ｎ−ジメチルホルムアミド
（２０ｍＡ’）に）８解した後、水酸化ナトリウム（０
，１８ｇ）を加え、４〇−５０℃で３時間加熱した。反
応液に水を加えベンゼンで抽出した。分離したベンゼン
層を水洗、乾燥後、留去して得られた粗生成物を分取用
薄層クロマトグラフィー（展開液：ベンゼン／酢酸エチ
ル＝ ４ ／ １ ｖ／ｖ）で分離、精製し、標記目的
物の結晶（０，７７ｇ）を得た。Melting point: 89-91'C 2-tert-butyl-4-(methoxymethylthio)-5-(
Production of 4-t-butylbenzylthio)-3(2H)-pyridazinone (compound 1t261) 4 synthesized in Production Example 5
-Mercapto compound (1.5 g) and chloromethyl methyl ether (0.37 g) were dissolved in N,N-dimethylformamide (20 mA'), and then sodium hydroxide (0.8 mA') was dissolved.
, 18g) and heated at 40-50°C for 3 hours. Water was added to the reaction solution and extracted with benzene. The separated benzene layer was washed with water, dried, and distilled off, and the resulting crude product was separated and purified by preparative thin layer chromatography (developing solution: benzene/ethyl acetate = 4/1 v/v), Crystals (0.77 g) of the title target product were obtained.
融点：９４−９７℃
次に製造例１〜６の方法に準じて製造した化合物の製造
例を第３表に記載した。化合物の番号は第１表および第
２表に対応する。Melting point: 94-97°C Next, production examples of compounds produced according to the methods of Production Examples 1 to 6 are listed in Table 3. Compound numbers correspond to Tables 1 and 2.
第 ３ 表
２６１００−１０３ １８０５５．０−５６．５８３９
１−９４ ２３２８３．５−８６．０９１（油状物）”
２５１ ８９−９１９２（油状物）
２５２ １４２−１４４９３（油状物）
２６１ ９４’−９７９４６０−６２２６５（
油状物）Ｏ
１２６５９，０−６１，０３４４１２９−１３０＊ Ｎ
ＭＲ（δ値） ： ０．９−１．８ （ｍ、７１１）
、１．６０ （ｓ、９１１）、２．５−２．８ （ｍ、
２８）、３．９７ （Ｓ、３Ｈ）、５．１９ （ｓ、２
１１）、７．２ （ｂｓ、４Ｈ）、７．５９ （ｓ、１
１１）。Table 3 26100-103 18055.0-56.5839
1-94 23283.5-86.091 (oil)”
251 89-9192 (oil)
252 142-14493 (oil)
261 94'-979460-62265(
Oily substance) O 12659,0-61,0344129-130*N
MR (δ value): 0.9-1.8 (m, 711)
, 1.60 (s, 911), 2.5-2.8 (m,
28), 3.97 (S, 3H), 5.19 (s, 2
11), 7.2 (bs, 4H), 7.59 (s, 1
11).
＊ ＊ ＮＭＲ（δ値） ： １．２５ （ｓ、９ｆ
ｌ） 、１．６０ （ｓ、９１１）、１．８５ （ｂｓ
、４Ｈ）、４．０２ （ｓ、２Ｈ） 、７．１−７．３
（ｍ、９１１）、７．５７ （ｓ、ＩＨ）。* * NMR (δ value): 1.25 (s, 9f
l), 1.60 (s, 911), 1.85 (bs
, 4H), 4.02 (s, 2H), 7.1-7.3
(m, 911), 7.57 (s, IH).
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）
、酸アミド頻（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、：Ｕ層剤、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、フロワブル剤等
任意の剤型にて実用に供することができる。また、必要
に応じて調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。When the compound of the present invention is used as an agricultural and horticultural insecticide, acaricide, nematicide, and a mite repellent for animals, it is generally carried out using a suitable carrier, such as a solid carrier such as clay, talc, bentonite, or diatom. Or water, alcohols (methanol, ethanol, etc.), aromatic hydrocarbons (
benzene, toluene, xylene, etc.), chlorinated hydrocarbons, ethers, ketones, esters (ethyl acetate, etc.)
It can be applied in combination with a liquid carrier such as an acid amide (such as dimethylformamide), and if desired, an emulsifier,
By adding dispersants, U-layer agents, penetrating agents, spreading agents, stabilizers, etc., it can be put to practical use in any dosage form such as liquids, emulsions, wettable powders, powders, granules, and flowables. . Further, if necessary, it may be applied in combination with other herbicides, various insecticides, fungicides, plant growth regulators, synergists, etc. at the time of preparation or spraying.
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最に
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 the maximum 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
がこれらのみに限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, nematicides, 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.
■鼾 乳剤
本発明化合物 −−−−−−−−２０部
キシレン −−−−−−−−５５部
Ｎ、Ｎ−ジメチルボルムアミドー−−−−−−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（掬商品名）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ｏ、ｏｏｓ
〜５０ｋｇになるように散布する。■Snoring Emulsion Compound of the present invention ---20 parts Xylene ---55 parts N,N-dimethylborumamide ---20 parts Trupol 2680 --- ----- 5 copies (
Mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industries (Kiku brand name) and above are mixed uniformly to form an emulsion. When using the above emulsion, 50 to 20,000
Dilute to 2 times the amount of active ingredient per hectare, o, oos
Spread to make it weigh up to 50 kg.
繋剋適叢 水和剤
本発明化合物 −−−−−−−−２５部
ジークライトＰ Ｆ Ｐ −−−−−−−−
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■商品名）
ツルポール５０３９ −−−−−−− ４部（
アニオン性界面活性剤
：東邦化学工業側商品名）
カープレックス＃８０ −−−−−−−３部（ホ
ワイトカーボン：塩野義製薬■商品名）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。Wettable powder Compound of the present invention ------- 25 parts Sieglite P F P ----------
66 parts (mixture of kaolinite and sericite; Zeeklite Industries ■trade name) Tsurupol 5039 ------- 4 parts (
Anionic surfactant: Toho Chemical Co., Ltd. brand name) Carplex #80 -------3 parts (white carbon: Shionogi & Co., Ltd. brand name) Calcium lignin sulfonate---2 parts or more Mix and grind them uniformly to make a wettable powder.
使用に際しては上記水和剤を５０〜２００００倍に希釈
して有効成分量かへクタール当たり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 k per hectare.
Spread it so that it becomes
１ｍ例」−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。1m Example" - Oil agent Compound of the present invention -------- 10 parts 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.
事■士倒〕ユ 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０１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
有効成分量がへクタール当たり０．００５〜５０ｋｇに
なるように散布する。Compound of the present invention ------- 3.0 parts Carplex #80 ---------- 0.
5 parts (white carbon: Shionogi & Co., Ltd. 01 trade name) Clay -------95 parts Diisopropyl phosphate---1.5 parts or more are uniformly mixed and pulverized to form a powder. In use, the above-mentioned powder is spread so that the amount of active ingredient is 0.005 to 50 kg per hectare.
Ｕ駐 粒剤
本発明化合物 −一−−−−−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ー−−−−−−１部以上を均一
に混合粉砕して少量の水を加えて攪拌混合し、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。U Granule agent 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■貫Ｌ 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（掬商品名）ルノ
ソクス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（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５０〜２００
００倍に希釈して有効成分量かへクタール当たりｏ、ｏ
ｏｓ〜５０ｋｇになるように散布する。Seikan L Flowable agent Compound of the present invention ------- 25 parts Tsurupol 3353 ------- 10 parts (
Nonionic surfactant: Toho Chemical Co., Ltd. (trade name) Lunosox 100OC---0.5 parts (anionic surfactant: Toho Chemical Co., Ltd. trade name) 1% xanthan gum aqueous solution ----- ---20 parts (natural polymer) Water ------
-44.5 parts Remove the active ingredient (the compound of the present invention) (dissolve the above ingredients uniformly, then add the compound of the present invention, stir well, and wet-mill in a sand mill to obtain a flowable agent. , 50 to 200 of the above flowable agent
00 times diluted and the amount of active ingredient is o, o per hectare.
Spray to os~50kg.
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、果樹および硫
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 compound of the present invention has excellent insecticidal power against Hemiptera pests such as leafhopper, Lepidoptera pests such as diamondback moth, Coleoptera pests, and sanitary pests such as Culex mosquito, and also has excellent insecticidal power against various mites that parasitize fruit trees and sulfur vegetables, 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.
ｍ 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。m Insecticidal test against black leafhopper An 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、９２ 、Ｎｏ、９３ 、Ｎｏ、９
４、Ｎｏ、 １２６
跋緩開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. 92, No. 93, No. 9
4, No, 126 Slow release 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、９２ 、Ｎｏ、１２６拭鋏±１
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 ａｍのスチロールカップ上の湿っ
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ｌＯ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１１０００ｐ
ｐ Ｑ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２ｍｌ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。Compound of the present invention No. 92, No. 126 Wiping scissors ±1
Acaricidal efficacy test against Kanzawa spider mites Green bean leaves were cut into circles with a diameter of 1.5 cm using a leaf punch and placed on moist filter paper on a styrene cup with a diameter of 7 am. This was inoculated with one light or 10 Kanzawa spider mite larvae. 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 11,000p.
A chemical solution of p Q degree was prepared. This chemical solution was sprayed at a rate of 2 ml per styrene cup using a rotary scattering tower, and
The mortality rate after the passage of time was calculated using the following formula. In addition,
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、２６ 、Ｎｏ、８３ 、Ｎｏ、９
１ 、Ｎｏ、９２Ｎｏ、９３ 、Ｎｏ、９４ 、Ｎｏ、
１２６跋駿炭エ ネコブ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 ？ｍ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
１ずつ土壌に潅注した。４８時間経過後に指標作物のト
マＩ・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. 26, No. 83, No. 9
1, No, 92No, 93, No, 94, No,
Nematicidal efficacy test against Nematode nematode Contaminated soil of Nematode 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 give a concentration of 11,000 pp? A chemical solution of m degree was prepared. 50m of this chemical solution per styrofoam cup.
1 was irrigated into the soil. After 48 hours, seedlings of Toma I, an 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、９２Compound of the present invention No. 92
Claims (2)
びＤは、それぞれ独立に酸素原子または硫黄原子を表し
、Ａは炭素数１〜４のアルコキシ基、炭素数１〜４のハ
ロアルコキシ基、炭素数１〜４のアルキルチオ基、炭素
数１〜４のハロアルキルチオ基、アルコキシメチルチオ
基、ＳＨ基または▲数式、化学式、表等があります▼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、Ｑ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▼または▲数式、化学
式、表等があります▼を表し、Ｙはハロゲ ン原子、炭素数１〜６のアルキル基、炭素数３〜６のシ
クロアルキル基、炭素数２〜６のアルケニル基、炭素数
３〜６のシクロアルコキシ基、炭素数１〜６のアルコキ
シ基、炭素数１〜６のアルキルチオ基、アルキルスルホ
ニル基、炭素数１〜４のハロアルキル基、ハロアルコキ
シ基、ハロアルキルチオ基、炭素数２〜４のアルケニル
オキシ基、炭素数１〜４のアルコキシカルボニル基、ト
リメチルシリル基、ジメチルアミノ基、ニトロ基、シア
ノ基、▲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、Ｚ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、Ｒ＾６およびＲ＾７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、Ｒ＾８は炭
素数１〜４のアルキル基を表し、ｎは０、１〜３の整数
を表し、ｌは０、１〜４の整数を表す。〕(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, X and D each independently represent an oxygen atom or a sulfur atom, and A is an alkoxy group having 1 to 4 carbon atoms; Represents a haloalkoxy group, an alkylthio group having 1 to 4 carbon atoms, a haloalkylthio group having 1 to 4 carbon atoms, an alkoxymethylthio group, an SH group, or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, R^1 and R^2 Each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, B represents ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and R^3 and R^4 each independently represent a hydrogen atom or a carbon atom. Represents an alkyl group of numbers 1 to 4, m represents 0 or 1, and Q represents ▲Mathematical formulas, chemical formulas, tables, etc.▼, ▲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 Y is a halogen atom, an alkyl group with 1 to 6 carbon atoms, Cycloalkyl group having 3 to 6 carbon atoms, alkenyl group having 2 to 6 carbon atoms, cycloalkoxy group having 3 to 6 carbon atoms, alkoxy group having 1 to 6 carbon atoms, alkylthio group having 1 to 6 carbon atoms, alkylsulfonyl group , a haloalkyl group having 1 to 4 carbon atoms, a haloalkoxy group, a haloalkylthio group, an alkenyloxy group having 2 to 4 carbon atoms, an alkoxycarbonyl group having 1 to 4 carbon atoms, a trimethylsilyl group, a dimethylamino group, a nitro group, a cyano group , ▲ There are mathematical formulas, 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.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and Z represents 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. R^6 and R^7 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R^8 represents an alkyl group having 1 to 4 carbon atoms, and n is 0, 1 to 3 represents an integer of 0, l represents an integer of 1 to 4. ]
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、Ｘおよ
びＤは、それぞれ独立に酸素原子または硫黄原子を表し
、Ａは炭素数１〜４のアルコキシ基、炭素数１〜４のハ
ロアルコキシ基、炭素数１〜４のアルキルチオ基、炭素
数１〜４のハロアルキルチオ基、アルコキシメチルチオ
基、ＳＨ基または▲数式、化学式、表等があります▼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、Ｑ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▼または▲数式、化学
式、表等があります▼を表し、Ｙはハロゲ ン原子、炭素数１〜６のアルキル基、炭素数３〜６のシ
クロアルキル基、炭素数２〜６のアルケニル基、炭素数
３〜６のシクロアルコキシ基、炭素数１〜６のアルコキ
シ基、炭素数１〜６のアルキルチオ基、アルキルスルホ
ニル基、炭素数１〜４のハロアルキル基、ハロアルコキ
シ基、ハロアルキルチオ基、炭素数２〜４のアルケニル
オキシ基、炭素数１〜４のアルコキシカルボニル基、ト
リメチルシリル基、ジメチルアミノ基、ニトロ基、シア
ノ基、▲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、Ｚ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、Ｒ＾６およびＲ＾７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、Ｒ＾８は炭
素数１〜４のアルキル基を表し、ｎは０、１〜３の整数
を表し、ｌは０、１〜４の整数を表す。〕(2) General formula [I]: ▲There are mathematical formulas, chemical formulas, tables, etc.▼It is characterized by containing one or more 3(2H)-pyridazinone derivatives represented by [I] as an active ingredient. Agricultural and horticultural insecticides, acaricides, nematocides, and mites that are parasitic on animals. [In the formula, R represents an alkyl group having 1 to 6 carbon atoms, X and D each independently represent an oxygen atom or a sulfur atom, and A is an alkoxy group having 1 to 4 carbon atoms; Represents a haloalkoxy group, an alkylthio group having 1 to 4 carbon atoms, a haloalkylthio group having 1 to 4 carbon atoms, an alkoxymethylthio group, an SH group, or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, R^1 and R^2 Each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, B represents ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and R^3 and R^4 each independently represent a hydrogen atom or a carbon atom. Represents an alkyl group of numbers 1 to 4, m represents 0 or 1, and Q represents ▲Mathematical formulas, chemical formulas, tables, etc.▼, ▲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 Y is a halogen atom, an alkyl group with 1 to 6 carbon atoms, Cycloalkyl group having 3 to 6 carbon atoms, alkenyl group having 2 to 6 carbon atoms, cycloalkoxy group having 3 to 6 carbon atoms, alkoxy group having 1 to 6 carbon atoms, alkylthio group having 1 to 6 carbon atoms, alkylsulfonyl group , a haloalkyl group having 1 to 4 carbon atoms, a haloalkoxy group, a haloalkylthio group, an alkenyloxy group having 2 to 4 carbon atoms, an alkoxycarbonyl group having 1 to 4 carbon atoms, a trimethylsilyl group, a dimethylamino group, a nitro group, a cyano group , ▲ There are mathematical formulas, 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.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, where Z is a halogen atom, an alkyl group with 1 to 4 carbon atoms, or a 1 to 4 carbon atom. It represents an alkoxy group, a haloalkyl group having 1 to 4 carbon atoms, or a nitro group, R^6 and R^7 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and R^8 represents an alkyl group having 1 to 4 carbon atoms. ~4 alkyl group, n represents 0, an integer of 1-3, l represents 0, an integer of 1-4. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30639486A JPS63159372A (en) | 1986-12-24 | 1986-12-24 | Pyridazinone compound and insecticide, acaricide and nematocide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30639486A JPS63159372A (en) | 1986-12-24 | 1986-12-24 | Pyridazinone compound and insecticide, acaricide and nematocide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63159372A true JPS63159372A (en) | 1988-07-02 |
Family
ID=17956486
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP30639486A Pending JPS63159372A (en) | 1986-12-24 | 1986-12-24 | Pyridazinone compound and insecticide, acaricide and nematocide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63159372A (en) |
Cited By (7)
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|---|---|---|---|---|
| CN1038025C (en) * | 1994-01-22 | 1998-04-15 | 李士才 | Non-environmental-pollution food package and manufacturing method thereof |
| WO2010113986A1 (en) * | 2009-03-30 | 2010-10-07 | 住友化学株式会社 | Use of pyridazinone compound for control of harmful arthropod pests |
| JP2013047277A (en) * | 2004-02-13 | 2013-03-07 | Bristol-Myers Squibb Pharma Co | Contrast agent for myocardial perfusion imaging |
| US8936777B2 (en) | 2010-02-08 | 2015-01-20 | Lantheus Medical Imaging, Inc. | Methods and apparatus for synthesizing imaging agents, and intermediates thereof |
| US9408927B2 (en) | 2008-02-29 | 2016-08-09 | Lantheus Medical Imaging, Inc. | Contrast agents for applications including perfusion imaging |
| US9713651B2 (en) | 2012-08-10 | 2017-07-25 | Lantheus Medical Imaging, Inc. | Compositions, methods, and systems for the synthesis and use of imaging agents |
| WO2023204124A1 (en) * | 2022-04-20 | 2023-10-26 | 日本曹達株式会社 | Pyridazinone compound, agricultural and horticultural germicide, nematicide, and medical and veterinary antifungal agent |
-
1986
- 1986-12-24 JP JP30639486A patent/JPS63159372A/en active Pending
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1038025C (en) * | 1994-01-22 | 1998-04-15 | 李士才 | Non-environmental-pollution food package and manufacturing method thereof |
| US9161997B2 (en) | 2001-08-16 | 2015-10-20 | David S. Casebier | Contrast agents for myocardial perfusion imaging |
| US9718786B2 (en) | 2004-02-13 | 2017-08-01 | Lantheus Medical Imaging, Inc. | Contrast agents for myocardial perfusion imaging |
| US10125106B2 (en) | 2004-02-13 | 2018-11-13 | Lantheus Medical Imaging, Inc. | Contrast agents for myocardial perfusion imaging |
| JP2013047277A (en) * | 2004-02-13 | 2013-03-07 | Bristol-Myers Squibb Pharma Co | Contrast agent for myocardial perfusion imaging |
| US10889550B2 (en) | 2004-02-13 | 2021-01-12 | Lantheus Medical Imaging, Inc. | Contrast agents for myocardial perfusion imaging |
| US9408927B2 (en) | 2008-02-29 | 2016-08-09 | Lantheus Medical Imaging, Inc. | Contrast agents for applications including perfusion imaging |
| US10245332B2 (en) | 2008-02-29 | 2019-04-02 | Lantheus Medical Imaging, Inc. | Contrast agents for applications including perfusion imaging |
| WO2010113986A1 (en) * | 2009-03-30 | 2010-10-07 | 住友化学株式会社 | Use of pyridazinone compound for control of harmful arthropod pests |
| US9603951B2 (en) | 2010-02-08 | 2017-03-28 | Lantheus Medical Imaging, Inc. | Methods and apparatus for synthesizing imaging agents, and intermediates thereof |
| US10022462B2 (en) | 2010-02-08 | 2018-07-17 | Lantheus Medical Imaging, Inc. | Methods and apparatus for synthesizing imaging agents, and intermediates thereof |
| US10842892B2 (en) | 2010-02-08 | 2020-11-24 | Lantheus Medical Imaging, Inc. | Methods and apparatus for synthesizing imaging agents, and intermediates thereof |
| US8936777B2 (en) | 2010-02-08 | 2015-01-20 | Lantheus Medical Imaging, Inc. | Methods and apparatus for synthesizing imaging agents, and intermediates thereof |
| US9919064B2 (en) | 2012-08-10 | 2018-03-20 | Lantheus Medical Imaging, Inc. | Compositions, methods, and systems for the synthesis and use of imaging agents |
| US9713651B2 (en) | 2012-08-10 | 2017-07-25 | Lantheus Medical Imaging, Inc. | Compositions, methods, and systems for the synthesis and use of imaging agents |
| US10500293B2 (en) | 2012-08-10 | 2019-12-10 | Lantheus Medical Imaging, Inc. | Compositions, methods, and systems for the synthesis and use of imaging agents |
| US11744906B2 (en) | 2012-08-10 | 2023-09-05 | Lantheus Medical Imaging, Inc. | Compositions, methods, and systems for the synthesis and use of imaging agents |
| WO2023204124A1 (en) * | 2022-04-20 | 2023-10-26 | 日本曹達株式会社 | Pyridazinone compound, agricultural and horticultural germicide, nematicide, and medical and veterinary antifungal agent |
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