JPS63159374A - Pyridazinone derivative and insecticide, acaricide and nematocide - Google Patents
Pyridazinone derivative and insecticide, acaricide and nematocideInfo
- Publication number
- JPS63159374A JPS63159374A JP30639386A JP30639386A JPS63159374A JP S63159374 A JPS63159374 A JP S63159374A JP 30639386 A JP30639386 A JP 30639386A JP 30639386 A JP30639386 A JP 30639386A JP S63159374 A JPS63159374 A JP S63159374A
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- JP
- Japan
- Prior art keywords
- carbon atoms
- tables
- formulas
- group
- 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
- 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 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 34
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 13
- 241001465754 Metazoa Species 0.000 claims abstract description 9
- 241000238876 Acari Species 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 230000003071 parasitic effect Effects 0.000 claims abstract description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 56
- 239000000126 substance Substances 0.000 claims description 36
- 239000004480 active ingredient Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 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
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 47
- 239000002904 solvent Substances 0.000 abstract description 10
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 239000012433 hydrogen halide Substances 0.000 abstract description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract description 3
- 239000002250 absorbent Substances 0.000 abstract description 2
- 230000002745 absorbent Effects 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- 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 17
- 239000003795 chemical substances by application Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 239000000839 emulsion 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000749 insecticidal effect Effects 0.000 description 6
- 241000244206 Nematoda Species 0.000 description 5
- 241000607479 Yersinia pestis Species 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 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
- 239000000843 powder Substances 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material 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
- 238000005406 washing Methods 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 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
- 241001414720 Cicadellidae Species 0.000 description 2
- 241000255749 Coccinellidae Species 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
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 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
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-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
- 235000013399 edible fruits Nutrition 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- NPGJBWRAAZWXQD-UHFFFAOYSA-N 1-[4-(bromomethyl)phenyl]-2,2,2-trifluoroethanone Chemical compound FC(F)(F)C(=O)C1=CC=C(CBr)C=C1 NPGJBWRAAZWXQD-UHFFFAOYSA-N 0.000 description 1
- SNLNKUQSMCQSJL-UHFFFAOYSA-N 1-[4-(bromomethyl)phenyl]-2,2-dimethylpropan-1-one Chemical compound CC(C)(C)C(=O)C1=CC=C(CBr)C=C1 SNLNKUQSMCQSJL-UHFFFAOYSA-N 0.000 description 1
- DGHDHWFHJPGAGC-UHFFFAOYSA-N 1-[4-(bromomethyl)phenyl]-2-methylpropan-1-one Chemical compound CC(C)C(=O)C1=CC=C(CBr)C=C1 DGHDHWFHJPGAGC-UHFFFAOYSA-N 0.000 description 1
- -1 2,2,2-trifluoroethoxycarbonyl Chemical group 0.000 description 1
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
- QSMJDUYHPSVTBH-UHFFFAOYSA-N 4-chloro-2-ethyl-5-hydroxypyridazin-3-one Chemical compound CCN1N=CC(O)=C(Cl)C1=O QSMJDUYHPSVTBH-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 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
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- 206010011732 Cyst Diseases 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
- 241000258937 Hemiptera Species 0.000 description 1
- 239000005909 Kieselgur Substances 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
- 241001480837 Rhipicephalus annulatus Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 240000003768 Solanum lycopersicum Species 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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-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
- 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
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- WZPMZMCZAGFKOC-UHFFFAOYSA-N diisopropyl hydrogen phosphate Chemical compound CC(C)OP(O)(=O)OC(C)C WZPMZMCZAGFKOC-UHFFFAOYSA-N 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
- 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
- GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 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
- 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
- 230000014759 maintenance of location Effects 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
- 230000024241 parasitism Effects 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
- 229910000027 potassium carbonate Inorganic materials 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000004576 sand Substances 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
- 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
- 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
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000001238 wet grinding 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
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
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（ｎ）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）１ぜ０
〔式中、例えばＲ′はアルキル基、Ａ′はハロゲン原子
、Ｒ’ｌおよびＲ８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（ｎ）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 (n) have insecticidal, acaricidal, nematicidal, and bactericidal effects for agricultural and horticultural purposes. . (Refer to European Published Patent No. 0088384, European Published Patent No. 0134439, and European Published Patent No. 0183212) 1ze0 [In the formula, for example, R' is an alkyl group, A' is a halogen atom, R'l and R8 is a hydrogen atom or a lower alkyl group,
X' represents an oxygen atom or a sulfur atom, and 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, or the like. ] 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 (n), 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、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
、Ｒｌ、 ＲＺ、 Ｒ３およびＲ′は、それぞれ独立に
水素原子または炭素数１〜４の低級アルキル基を表し、
ｍは０または１を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、ニトロ基、
炭素数１〜４のアルキルチオ基、または炭素数１〜４の
アルキルスルホニル基を表し、ｎは０．１または２を表
し、Ｚは炭素数１〜９のアルキル基、炭素数２〜８のア
ルケニル基、炭素数１〜９のハロアルキル基、炭素数１
〜６のハロアルコキシ基、炭素数２〜４のアルケニルオ
キシ基、炭素数２〜４のアルキニルオキシ基、炭素数１
〜４のアルキの整数を表し、Ｒ５は水素原子または炭素
数１〜４のアルキル基を表し、Ｒ６は水素原子、炭素数
１〜４のアルキル基、炭素数１〜４のハロアルキル基、
炭素数１〜４のアルキルカルボニル基、で表される３（
２Ｈ）−ビ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]: [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, X represents an oxygen atom or a sulfur atom, and Rl, RZ, R3, and R' each independently represent a hydrogen atom or a represents a lower alkyl group of
m is 0 or 1 to 4 alkyl group, alkoxy group having 1 to 4 carbon atoms, haloalkyl group having 1 to 4 carbon atoms, nitro group,
represents an alkylthio group having 1 to 4 carbon atoms or an alkylsulfonyl group having 1 to 4 carbon atoms, n represents 0.1 or 2, and Z is an alkyl group having 1 to 9 carbon atoms, an alkenyl group having 2 to 8 carbon atoms; group, haloalkyl group having 1 to 9 carbon atoms, 1 carbon number
-6 haloalkoxy group, C2-4 alkenyloxy group, C2-4 alkynyloxy group, C1
represents an integer of alkyl of ~4, R5 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R6 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms,
3(
The present invention relates to a 2H)-pyridazinone derivative and an insecticide for agricultural and horticultural use, an acaricide, a 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
、Ｅｔはエチル基を、Ｐｒはプロピル基を、Ｂｕはブチ
ル基を、【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 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 is a methyl group, Et is an ethyl group, Pr is a propyl group, Bu is a butyl group, [ is tertiary, S is secondary, i
indicates iso. ] 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
〔以下、余白〕
第２表
〔以下、余白〕
第２表中の０１〜Ｇ２３は、次の構造式で表される基で
ある。Table 1 (hereinafter referred to as margins) Table 2 (hereinafter referred to as margins) 01 to G23 in Table 2 are groups represented by the following structural formulas.
本発明化合物は、次の反応式に従って製造できる。The compound of the present invention can be produced according to the following reaction formula.
（１） （ＩＶ）本発明化合
物（１）
〔式中、Ｒ，Ｒ’ 、Ｒ”、Ｒ３，Ｒ’、Ａ、Ｑ。(1) (IV) Compound (1) of the present invention [wherein R, R', R'', R3, R', A, Q.
Ｚおよびｍは前記と同じ意味を表し、Ｘｌはハロゲン原
子、−０１１または一５ｉを表し、Ｘ２はハロゲン原子
、−０１１または−５１１を表す。但し、ＸＩがハロゲ
ン原子の場合はＸ２は−ＯＨまたは−ＳＨを表し、Ｘ２
が−０１１または−ＳＨの場合はＸ２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（ＩＩＩ）で表される３（２）１）−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。Z and m represent the same meanings as above, Xl represents a halogen atom, -011 or -5i, and X2 represents a halogen atom, -011 or -511. However, when XI is a halogen atom, X2 represents -OH or -SH, and X2
When is -011 or -SH, X2 represents a halogen atom. ] That is, the compound (1) of the present invention consists of a 3(2)1)-pyridazinone derivative represented by the above formula (III), which is one of the raw materials, and a 3(2)1)-pyridazinone derivative represented by the above formula (IV), which is the other raw material. It can be produced by reacting a compound with a hydrogen halide absorbent in a solvent that does not affect the reaction.
Ru. 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, 1°4-dioxane, etc.), amides (e.g., N,N-dimethylformamide, hexamethyl Phosphoric 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） 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.
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.
！！ｌＬＬ ２− ｔ−ブチル−４−クロロ−５−（４
−ピバロイルベンジルチオ）−３
（２Ｈ）−ピリダジノンの合成
（化合物階４０）
２−ｔ−ブチル−４−クロロ−５−メルカプト−３（２
Ｈ）−ピリダジノン（１，０９ｇ）および４−ピバロイ
ルベンジルブロマイド（１，２８ｇ）をＮ、Ｎ−ジメチ
ルホルムアミド（１０ｍｌりに熔解し、炭酸ナトリウム
（０，５３ｇ）を加え室温にて１８時間撹拌した。この
？８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−エタノールにて再結晶し、標記目的物（
１，８３ｇ）を得た。! ! lLL 2-t-butyl-4-chloro-5-(4
-pivaloylbenzylthio)-3 (2H)-Synthesis of pyridazinone (compound level 40) 2-t-butyl-4-chloro-5-mercapto-3(2
H)-pyridazinone (1,09 g) and 4-pivaloylbenzyl bromide (1,28 g) were dissolved in N,N-dimethylformamide (10 ml), and sodium carbonate (0,53 g) was added thereto at room temperature for 18 hours. This ?8 liquid was poured into water and 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-ethanol. thing(
1.83 g) was obtained.
融点１３９．８〜１４３．１℃
製遺拠１４−クロロ−２−エチル−５−（４−イソブチ
リルベンジルオキシ）−３
（２Ｈ）−ピリダジノンの合成
（化合物ｔ’ｈ３３）
４−クロロ−２−エチル−５−ヒドロキシ−３（２Ｈ）
−ピリダジノン（０，８７ｇ）および４−イソプチリル
ベンジルブロマイド（１，２１ｇ）をＮ、Ｎ−ジメチル
ホルムアミド（１０ｎｌ）に熔解し、炭酸ナトリウム（
０，５３ｇ）を加え室温にて１８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−ベンゼンにて再結晶し、標記目的物（１，２
６ｇ）を得た。Melting point: 139.8-143.1°C Synthesis of 14-chloro-2-ethyl-5-(4-isobutyrylbenzyloxy)-3 (2H)-pyridazinone (compound t'h33) 4-chloro- 2-ethyl-5-hydroxy-3(2H)
-Pyridazinone (0,87 g) and 4-isobutyrylbenzyl bromide (1,21 g) were dissolved in N,N-dimethylformamide (10 nl), and sodium carbonate (
0.53 g) was added thereto, and the mixture was stirred at room temperature for 18 hours. 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 crystals were recrystallized from hexane-benzene to obtain the title target (1,2
6g) was obtained.
融点８２．０〜８５．６℃
１遣１２−ｔ−ブチルー４−クロロ−５−（４−トリフ
ルオロアセチルベンジル
チオ）−３（２Ｈ）−ピリダジノンの
合成
（化合物隘７０）
４′−メチル−２，２，２−トリフルオローアセトフェ
）ン（２，７９ｇ） 、Ｎ−プロモーコハク酸イミド（
２，６４ｇ）および過酸化ベンゾイル（０，１ｇ）を四
塩化炭素（２０ｎ７りに溶解し還流下１時間撹拌した。Melting point: 82.0-85.6°C Synthesis of 1-12-t-butyl-4-chloro-5-(4-trifluoroacetylbenzylthio)-3(2H)-pyridazinone (compound 70) 4'-Methyl- 2,2,2-trifluoroacetophene (2,79 g), N-promo succinimide (
2.64g) and benzoyl peroxide (0.1g) were dissolved in carbon tetrachloride (20ml) and stirred under reflux for 1 hour.
室温まで冷却後、コハク酸イミド −をろ別し、
減圧下で溶媒を留去し、４−トリフルオロアセチルベン
ジルブロマイド（５，０９ｇ）を得た。After cooling to room temperature, succinimide was filtered off.
The solvent was distilled off under reduced pressure to obtain 4-trifluoroacetylbenzyl bromide (5.09 g).
２−ｔ−ブチル−４−クロロ−５−メルカプト−３（２
Ｈ）−ピリダシ／７（１，０９ｇ）および４−トリフル
オロアセチルヘンシルブロマイド（１，３３ｇ）をＮ、
Ｎ−ジメチルホルムアミド（１０ｍｌ）に溶解し、炭酸
ナトリウム（０，５３ｇ）を加え室温にて１８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−ベンゼンにて再結晶し、標記目
的物（１，６３ｇ）を得た。2-t-butyl-4-chloro-5-mercapto-3 (2
H)-pyridacy/7 (1,09 g) and 4-trifluoroacetylhensyl bromide (1,33 g) with N
The mixture was dissolved in N-dimethylformamide (10 ml), added with sodium carbonate (0.53 g), and stirred at room temperature for 18 hours. 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 crystals were recrystallized from hexane-benzene to obtain the title target (1.63 g ) was obtained.
融点１５８．０〜１６１．０℃
盟遣聞↓ ２−ｔ−ブチル−４−クロロ−５−〔４−（
２，２，２−トリフルオロエトキシカルボニル）ベンジ
ルチオ） −３（２）１） −ピリダジノンの合成 （
化合物隘１４４）
２−ｔ−ブチル−４−クロロ−５−メルカプト−３（２
Ｈ）−ピリダジノン（２，１ｇ）および４− （２，２
，２−）リフルオロエトキシカルボニル）ベンジルブロ
マイド（３，０ｇ）をＮ、Ｎ−ジメチルホルムアミド（
５０ｎｌ）に溶解し、炭酸ナトリウム（１，５ｇ）を加
え室温にて１０時間攪拌した。Melting point: 158.0-161.0℃ 2-t-butyl-4-chloro-5-[4-(
Synthesis of 2,2,2-trifluoroethoxycarbonyl)benzylthio)-3(2)1)-pyridazinone (
Compound 144) 2-t-butyl-4-chloro-5-mercapto-3 (2
H)-pyridazinone (2,1 g) and 4-(2,2
,2-)lifluoroethoxycarbonyl)benzyl bromide (3.0 g) was dissolved in N,N-dimethylformamide (
50 nl), added sodium carbonate (1.5 g), and stirred at room temperature for 10 hours.
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（３，６ｇ）
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 crystals were recrystallized from hexane to obtain the title object (3.6 g).
I got it.
融点１１８〜１２１”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: 118-121''C Next, Table 3 shows production examples of compounds produced according to the methods of Production Examples 1 to 4. The compound numbers correspond to Tables 1 and 2.
第 ３ 表
２７１４７．１−１５１．０ ７０１５８−１６１２８
１５９．８−１６７．９ １４３１１６−１１７３３８
２．０−８５．６ １４４１１８−１２１３９１２３．
０−１２４．１ ２１７１４９．５−１５０．５４０１
３９．８−１４３．１ ２１８１９３−１９５４５１２
０．３−１２２．３ ２７０１６２−１６３〔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、珪藻土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Ｒ（
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 3 27147.1-151.0 70158-16128
159.8-167.9 143116-117338
2.0-85.6 144118-12139123.
0-124.1 217149.5-150.5401
39.8-143.1 218193-1954512
0.3-122.3 270162-163 [Hereinafter, blank space] When using the compound of the present invention as an insecticide, acaricide, nematocide for agricultural and horticultural purposes, and as a repellent for mites parasitic on animals, an appropriate compound is generally used. A carrier, such as a solid carrier such as clay, talc, bentonite, diatomaceous earth, or water, alcohols (methanol, ethanol, etc.), aromatic hydrocarbons R (
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.
■Ｌ 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（牟菊商品名）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５０〜２０００
０倍に希釈して有効成分量がへクタール当たりｏ、、ｏ
ｏｓ〜５０ｋｇになるように散布する。■L Emulsion Compound of the present invention -------20 parts Xylene ---55 parts N,N-dimethylformamide ---20 parts Trupol 2680 --- --- 5 copies (
Mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industries (trade name: Mugiku) and above are mixed uniformly to form an emulsion. When using the above emulsion,
When diluted 0 times, the amount of active ingredient per hectare is o,,o
Spray to os~50kg.
製剤例２ 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■商品名）
カープレックス＃８０ −−−−−−− ３部（
ホワイトカーボン：塩野義製薬側商品名）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。Formulation Example 2 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 Industry ■Product name) Carplex #80 -------- 3 parts (
White carbon: Shionogi &Co.'s trade name) Calcium lignin sulfonate ------- 2 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
して有効成分量かへククール当たり０．００５〜５０ｋ
ｇになるように散布する。゛
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
剤を有効成分量がへクタール当たり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 50k per cup.
Spread it so that it becomes g.゛Formulation Example 3 Oil Agent - 10 parts of the compound of the present invention ------- 90 parts or more of Methyl Celsolve ------- 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 to 50k per hectare.
Spread it so that it becomes g.
■駐 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■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ｏ、ｏｏｓ〜５０ｋｇになるよ
うに散布する。■ Powder retention agent Compound of the present invention ---3.0 parts Carplex #80 ---0.5 parts (White Carbon: Shionogi & Co. ■Product 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 0,000 to 50 kg per hectare.
製１例」−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−−−−−−−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
粒剤を有効成分量かへクタール当たり０．００５〜５０
ｋｇになるように散布する。Preparation Example 1 - Granules Compound of the Invention --- 5 parts Bentonite --- 54 parts Talc --- 40 parts Calcium ligninsulfonate --- One or more parts are uniformly mixed and pulverized, a small amount of water is added, the mixture is stirred, the mixture is granulated using an extrusion type granulator, and the mixture is 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.
製剋炭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■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５０〜２０
０００倍に希釈して有効成分量がへクタール当たす０．
００５〜５０ｋｇになるように散布する。Planked coal L Flowable agent Compound of the present invention ------- 25 parts Tsurupol 3353 ------- 10 parts (
Nonionic surfactant: Toho Chemical Co., Ltd. (■Product name) Lunox 100OC---0.5 parts (Anionic surfactant: Toho Chemical Co., Ltd. (■Product 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 and stirred thoroughly, followed by wet grinding in a sand mill to obtain a flowable agent. When using, the above flowable agent should be added at a rate of 50 to 20
When diluted 1,000 times, the amount of active ingredient per hectare is 0.
0.005 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・アニュレイタス、アンプリオンマ・マク
レイタム、リビセファラス・アペンデイクラークス、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 annulatus, Amplionma maculatum, Libicephalus appendeiclarcus, and the staghorn 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
ンチエラ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 Nematode nematode, Negusare nematode, Cyst centiellae, etc.
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、２８ 、Ｎｏ、３９ 、Ｎｏ、４
０、Ｎｏ、４５
拭腋炭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、孔のあいた苦をして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. 28, No. 39, No. 4
0, No, 45 Wipe axillary charcoal 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 immersed in this chemical solution for about 10 seconds, air-dried, and then placed in a petri dish.Into this, 10 adult 2nd instar larvae of the Japanese ladybug per petri dish were placed. 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、２８ 、Ｎｏ、３９ 、Ｎｏ、２
１８Ｍ 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 ｃｍ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１１０００ｐ
ｐ 濃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２ｍβずつ回転弐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. 28, No. 39, No. 2
18M 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 styrofoam cup with a diameter of 7 cm. 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 11,000p.
A drug solution with a concentration of p was adjusted. This chemical solution was sprayed at a rate of 2 mβ per styrene cup using a rotating two-spraying tower.
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、２７ 、Ｎｏ、３９成醜拠土
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 ’（９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５０
ｍ１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、ネコプの寄生の見取り調査を行った。Compounds of the present invention No. 27, No. 39
Nematicidal efficacy test against Nematode nematode Contaminated soil with 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 prepare a 11,000 pp' (9%) chemical solution.
The soil was irrigated in an amount of 1 ml. 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 inspected for Nekopu parasitism.
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ゎがった。As a result, it was found that the following compounds exhibited strong nematicidal activity with almost no nematicidal activity observed.
Claims (2)
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、Ｒ＾２、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の低級アルキル基を表
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１〜４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、ニトロ基
、炭素数１〜４のアルキルチオ基、または炭素数１〜４
のアルキルスルホニル基を表し、ｎは０、１または２を
表し、Ｚは炭素数１〜９のアルキル基、炭素数２〜８の
アルケニル基、炭素数１〜９のハロアルキル基、炭素数
１〜６のハロアルコキシ基、炭素数２〜４のアルケニル
オキシ基、炭素数２〜４のアルキニルオキシ基、炭素数
１〜４のアルキルチオ基、ＯＨ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▼を表し、ｌは０、１〜５ の整数を表し、Ｒ＾５は水素原子または炭素数１〜４の
アルキル基を表し、Ｒ＾６は水素原子、炭素数１〜４の
アルキル基、炭素数１〜４のハロアルキル基、炭素数１
〜４のアルキルカルボニル基、▲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, 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, X represents an oxygen atom or a sulfur atom, and R^1, R^2, R^3 and R^4 each independently represent hydrogen. Represents an atom or a lower alkyl group having 1 to 4 carbon atoms, m represents 0 or 1, and Q represents ▲Mathematical formulas, chemical formulas, tables, etc.▼, ▲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. ▼
or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, where Y 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, a nitro group, a carbon Alkylthio group having 1 to 4 carbon atoms or 1 to 4 carbon atoms
represents an alkylsulfonyl group, n represents 0, 1 or 2, and Z represents an alkyl group having 1 to 9 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, a haloalkyl group having 1 to 9 carbon atoms, or a haloalkyl group having 1 to 9 carbon atoms. There are 6 haloalkoxy groups, alkenyloxy groups with 2 to 4 carbon atoms, alkynyloxy groups with 2 to 4 carbon atoms, alkylthio groups with 1 to 4 carbon atoms, OH groups, ▲ 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. ▼ represents 0, l represents an integer from 1 to 5, R^5 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R^6 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. alkyl group having 1 to 4 carbon atoms, haloalkyl group having 1 to 4 carbon atoms,
Represents ~4 alkylcarbonyl group, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼. ]
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、Ｒ＾２、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の低級アルキル基を表
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１〜４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、ニトロ基
、炭素数１〜４のアルキルチオ基、または炭素数１〜４
のアルキルスルホニル基を表し、ｎは０，１または２を
表し、Ｚは炭素数１〜９のアルキル基、炭素数２〜８の
アルケニル基、炭素数１〜９のハロアルキル基、炭素数
１〜６のハロアルコキシ基、炭素数２〜４のアルケニル
オキシ基、炭素数２〜４のアルキニルオキシ基、炭素数
１〜４のアルキルチオ基、ＯＨ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▼を表し、ｌは０，１〜５ の整数を表し、Ｒ＾５は水素原子または炭素数１〜４の
アルキル基を表し、Ｒ＾６は水素原子、炭素数１〜４の
アルキル基、炭素数１〜４のハロアルキル基、炭素数１
〜４のアルキルカルボニル基、▲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, 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, X represents an oxygen atom or a sulfur atom, and R^1, R^2, R^3 and R^4 each independently represent hydrogen. Represents an atom or a lower alkyl group having 1 to 4 carbon atoms, m represents 0 or 1, and Q represents ▲Mathematical formulas, chemical formulas, tables, etc.▼, ▲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. ▼
or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, where Y 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, a nitro group, a carbon Alkylthio group having 1 to 4 carbon atoms or 1 to 4 carbon atoms
represents an alkylsulfonyl group, n represents 0, 1 or 2, and Z represents an alkyl group having 1 to 9 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, a haloalkyl group having 1 to 9 carbon atoms, or a haloalkyl group having 1 to 9 carbon atoms. There are 6 haloalkoxy groups, alkenyloxy groups with 2 to 4 carbon atoms, alkynyloxy groups with 2 to 4 carbon atoms, alkylthio groups with 1 to 4 carbon atoms, OH groups, ▲ 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. ▼, l represents an integer from 0, 1 to 5, R^5 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and R^6 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. alkyl group having 1 to 4 carbon atoms, haloalkyl group having 1 to 4 carbon atoms,
Represents ~4 alkylcarbonyl group, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30639386A JPS63159374A (en) | 1986-12-24 | 1986-12-24 | Pyridazinone derivative and insecticide, acaricide and nematocide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30639386A JPS63159374A (en) | 1986-12-24 | 1986-12-24 | Pyridazinone derivative and insecticide, acaricide and nematocide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63159374A true JPS63159374A (en) | 1988-07-02 |
Family
ID=17956474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP30639386A Pending JPS63159374A (en) | 1986-12-24 | 1986-12-24 | Pyridazinone derivative and insecticide, acaricide and nematocide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63159374A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999001420A1 (en) * | 1997-07-03 | 1999-01-14 | Taito Co., Ltd. | Process for the preparation of 2-aminomalonic acid derivatives and intermediates used in the process |
| US9161997B2 (en) | 2001-08-16 | 2015-10-20 | David S. Casebier | 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 |
| US9713651B2 (en) | 2012-08-10 | 2017-07-25 | Lantheus Medical Imaging, Inc. | Compositions, methods, and systems for the synthesis and use of imaging agents |
| JPWO2016175017A1 (en) * | 2015-04-28 | 2018-02-22 | アグロカネショウ株式会社 | Novel 4-pyridinecarboxamide derivative and agricultural and horticultural agent containing this as an active ingredient |
| US10022462B2 (en) | 2010-02-08 | 2018-07-17 | Lantheus Medical Imaging, Inc. | Methods and apparatus for synthesizing imaging agents, and intermediates thereof |
-
1986
- 1986-12-24 JP JP30639386A patent/JPS63159374A/en active Pending
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999001420A1 (en) * | 1997-07-03 | 1999-01-14 | Taito Co., Ltd. | Process for the preparation of 2-aminomalonic acid derivatives and intermediates used in the process |
| 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 |
| US10889550B2 (en) | 2004-02-13 | 2021-01-12 | 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 |
| US10245332B2 (en) | 2008-02-29 | 2019-04-02 | Lantheus Medical Imaging, Inc. | Contrast agents for applications including perfusion imaging |
| US9408927B2 (en) | 2008-02-29 | 2016-08-09 | Lantheus Medical Imaging, Inc. | Contrast agents for applications including perfusion imaging |
| US10842892B2 (en) | 2010-02-08 | 2020-11-24 | 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 |
| 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 |
| US9919064B2 (en) | 2012-08-10 | 2018-03-20 | 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 |
| JPWO2016175017A1 (en) * | 2015-04-28 | 2018-02-22 | アグロカネショウ株式会社 | Novel 4-pyridinecarboxamide derivative and agricultural and horticultural agent containing this as an active ingredient |
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