JP7381913B2 - 有害生物防除組成物 - Google Patents
有害生物防除組成物 Download PDFInfo
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- JP7381913B2 JP7381913B2 JP2021168262A JP2021168262A JP7381913B2 JP 7381913 B2 JP7381913 B2 JP 7381913B2 JP 2021168262 A JP2021168262 A JP 2021168262A JP 2021168262 A JP2021168262 A JP 2021168262A JP 7381913 B2 JP7381913 B2 JP 7381913B2
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- WLCFKPHMRNPAFZ-UHFFFAOYSA-M didodecyl(dimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCC WLCFKPHMRNPAFZ-UHFFFAOYSA-M 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-N disulfuric acid Chemical compound OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 description 1
- TVACALAUIQMRDF-UHFFFAOYSA-N dodecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCOP(O)(O)=O TVACALAUIQMRDF-UHFFFAOYSA-N 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 125000005946 imidazo[1,2-a]pyridyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000010954 inorganic particle Substances 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 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
- 239000003350 kerosene Substances 0.000 description 1
- 235000021332 kidney beans Nutrition 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 229940031957 lauric acid diethanolamide Drugs 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- ZHALDANPYXAMJF-UHFFFAOYSA-N octadecanoate;tris(2-hydroxyethyl)azanium Chemical compound OCC[NH+](CCO)CCO.CCCCCCCCCCCCCCCCCC([O-])=O ZHALDANPYXAMJF-UHFFFAOYSA-N 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 235000011197 perejil Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000008103 phosphatidic acids Chemical class 0.000 description 1
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 235000021018 plums Nutrition 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000649 purine antagonist Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940117013 triethanolamine oleate Drugs 0.000 description 1
- 229940029614 triethanolamine stearate Drugs 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P3/00—Fungicides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P7/00—Arthropodicides
- A01P7/04—Insecticides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Mycology (AREA)
- Insects & Arthropods (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Saccharide Compounds (AREA)
Description
項1.
下記式(1):
R1及びR2は、それぞれ独立して、水素、1個以上の置換基を有していてもよい炭化水素基、R3CO-、又はスルファモイル基であり、
R3は、1個以上の置換基を有していてもよい炭化水素基であり、
Xは、水素、ハロゲン、ニトロ基、シアノ基、1個以上の置換基を有していてもよい炭化水素基、ヘテロアリール基、R4O-、R5S-、又はR6R7N-であり、
R4、R5、R6、及びR7は、それぞれ独立して、水素、又は1個以上の置換基を有していてもよい炭化水素基であり、
Zは、水素、ハロゲン、アジド基、シアノ基、又はR8O-であり、
R8は、1個以上の置換基を有していてもよい炭化水素基である。)
で表される化合物又はその塩を含有する有害生物防除組成物。
項2.
R1及びR2が、それぞれ独立して、水素、又はR3CO-である、項1に記載の有害生物防除組成物。
項3.
R3が、1個以上の置換基を有していてもよいアルキル基である、項1又は2に記載の有害生物防除組成物。
項4.
Xが、水素、ハロゲン、ニトロ基、シアノ基、アルキル基、アルケニル基、アルキニル基、シクロアルキル基、アリール基、ヘテロアリール基、R4O-、R5S-、又はR6R7N-であり、
R4、R5、R6、及びR7が、それぞれ独立して、水素、又は1個以上の置換基を有していてもよいアルキル基である、
項1~3のいずれか一項に記載の有害生物防除組成物。
項5.
Xが、ハロゲン、シアノ基、又はR4O-である、項1~4のいずれか一項に記載の有害生物防除組成物。
項6.
Xが、フッ素、塩素、又は臭素である、項1~5のいずれか一項に記載の有害生物防除組成物。
項7.
Zが、ハロゲンである、項1~6のいずれか一項に記載の有害生物防除組成物。
項8.
Zが、フッ素である、項1~7のいずれか一項に記載の有害生物防除組成物。
項9.
前記有害生物が、植物に対する病害虫又は病原菌である、項1~8のいずれか一項に記載の有害生物防除組成物。
項10.
前記植物が、イネ科植物、アブラナ科植物、ウリ科植物、マメ科植物、バラ科植物、及びブドウ科植物からなる群より選択される少なくとも一種である、項9に記載の有害生物防除組成物。
項11.
前記有害生物が、鱗翅目害虫、半翅目害虫、いもち病原菌、紋枯病原菌、炭疽病原菌、及び褐斑病原菌からなる群より選択される少なくとも一種である、項1~10のいずれか一項に記載の有害生物防除組成物。
項12.
植物に直接施用する、又は植物を栽培する土壌に施用するための、項1~11のいずれか一項に記載の有害生物防除組成物。
項13.
下記式(1a):
R1a及びR2aは、それぞれ独立して、1個以上の置換基を有していてもよい炭化水素基、R3aCO-、又はスルファモイル基であり、
R3aは、1個以上の置換基を有していてもよい炭化水素基であり、
Xaは、ハロゲン、ニトロ基、シアノ基、1個以上の置換基を有していてもよい炭化水素基、ヘテロアリール基、R4aO-、又はR5aS-であり、
R4a及びR5aは、それぞれ、水素、又は1個以上の置換基を有していてもよい炭化水素基であり、
Zaは、ハロゲン、アジド基、シアノ基、又はR8aO-であり、
R8aは、1個以上の置換基を有していてもよい炭化水素基である。)
で表される化合物又はその塩。
本明細書中の記号及び略号は、特に限定のない限り、本明細書の文脈に沿い、本開示が属する技術分野において通常用いられる意味に理解できる。
本開示の有害生物防除組成物は、下記式(1):
R1及びR2は、それぞれ独立して、水素、1個以上の置換基を有していてもよい炭化水素基、R3CO-、又はスルファモイル基(H2N-SO2-)であり、
R3は、1個以上の置換基を有していてもよい炭化水素基であり、
Xは、水素、ハロゲン、ニトロ基、シアノ基、1個以上の置換基を有していてもよい炭化水素基、ヘテロアリール基、R4O-、R5S-、又はR6R7N-であり、
R4、R5、R6、及びR7は、それぞれ独立して、水素、又は1個以上の置換基を有していてもよい炭化水素基であり、
Zは、水素、ハロゲン、アジド基(-N=N+=N-)、シアノ基、又はR8O-であり、
R8は、1個以上の置換基を有していてもよい炭化水素基である。)
で表される化合物又はその塩を含有する。
式(3)で表される化合物の代わりに2-アミノ-6-クロロ-9H-プロリンを用いる以外は工程Aと同様に実施する工程D、
工程Dにより得られた生成物を、亜硝酸又は亜硝酸エステル及び臭素源(例:CuBr、CH2Br2)又はヨウ素源(例:CuI、CH2I2)と反応(ザンドマイヤー反応)させる工程E、並びに
工程Eにより得られた生成物のプリン環の6位をアミノ化し、及びフラン環骨格の3’及び5’位のヒドロキシル基の保護基を脱保護する工程F
を含むことが好ましい。当該方法は、例えば国際公開第2020/213501号を参照することができる。
粉剤[例:式(1)で表される化合物又はその塩0.1~10質量%及び固体担体90~99.9質量%を含有する粉剤]、
顆粒剤[例:式(1)で表される化合物又はその塩0.1~30質量%及び固体担体70~99.5質量%を含有する顆粒剤]、
水和剤[例:式(1)で表される化合物又はその塩0.5~90質量%、固体担体5~95質量%、及び界面活性剤0.5~20質量%を含有する水和剤]、
懸濁液濃縮物[例:式(1)で表される化合物又はその塩5~75質量%、液体担体24~94質量%、及び界面活性剤1~40質量%を含有する懸濁液濃縮物]、又は
乳化性濃縮物[例:式(1)で表される化合物又はその塩1~95質量%、液体担体1~80質量%、及び界面活性剤1~30質量%を含有する懸濁液濃縮物]
であることができる。
本開示は、下記式(1a):
R1a及びR2aは、それぞれ独立して、1個以上の置換基を有していてもよい炭化水素基、R3aCO-、又はスルファモイル基であり、
R3aは、1個以上の置換基を有していてもよい炭化水素基であり、
Xaは、ハロゲン、ニトロ基、シアノ基、1個以上の置換基を有していてもよい炭化水素基、ヘテロアリール基、R4aO-、又はR5aS-であり、
R4a及びR5aは、それぞれ、水素、又は1個以上の置換基を有していてもよい炭化水素基であり、
Zaは、ハロゲン、アジド基、シアノ基、又はR8aO-であり、
R8aは、1個以上の置換基を有していてもよい炭化水素基である。)
で表される化合物又はその塩を包含する。
2-デオキシ-2-フルオロ-1,3,5-トリ-O-ベンゾイル-α-D-アラビノフラノース 5g(10.8mmol)を脱水ジクロロメタン 20 mLに溶解後、臭化水素-酢酸溶液(5.1 mol/L) 4.8 mL(24.5 mmol)を滴下し、16時間攪拌した。反応溶液にクロロホルムを加えた後、水、飽和炭酸水素ナトリウム水溶液、飽和食塩水の順に洗浄後、硫酸ナトリウムを加えて乾燥させた。この溶液をろ過した後、濃縮乾固することで化合物1を4.56g得た。
19F NMR (CDCl3, 400 MHz) δ: -165.73-165.95.
19F NMR (CDCl3, 400 MHz) δ: -198.35-198.59.
19F NMR (CD3CN, 400 MHz) δ: -198.12-198.88
化合物3 0.122g(0.4 mmol)を脱水ピリジン 3.0 mLに溶解後、4-メチルペンタノイルクロリド 0.127 mL(0.922 mmol)を添加し、16時間攪拌した。反応溶液にクロロホルムと3N HClを加えて分液した後、水洗した。このクロロホルム層を濃縮乾固した後、カラム精製を行うことで化合物4を0.145g得た。
19F NMR (CDCl3, 400 MHz) δ: -198.35-198.59
化合物3 0.122g(0.4 mmol)を脱水ピリジン 3.0 mLに溶解後、メトキシアセチルクロリド 0.084 mL(0.92 mmol)を添加し、16時間攪拌した。反応溶液にクロロホルムと3N HClを加えて分液した後、水洗した。このクロロホルム層を濃縮乾固した後、カラム精製を行うことで化合物5を0.123g得た。
19F NMR (CDCl3, 400 MHz) δ: -198.70-198.93.
化合物3 0.139g(0.46 mmol)を脱水ピリジン 5.0 mLに溶解後、ヘキサノイルクロリド 0.146 mL(1.05 mmol)を添加し、16時間攪拌した。反応溶液にクロロホルムと3N HClを加えて分液した後、水洗した。このクロロホルム層を濃縮乾固した後、カラム精製を行うことで化合物6を0.12g得た。
19F NMR (CDCl3, 400 MHz) δ: -198.35-198.60.
2-ブロモ-6-クロロプリン 9-β-D-(2'-デオキシ-3',5'-ジ-O-ベンゾイル-2'-フルオロ)アラビノリボサイド 1.05g(1.82 mmol)をテトラヒドロフラン 1.0 mL、アンモニウム/メタノール(2 M) 6 mLに溶解後、100℃で一晩攪拌した。反応溶液を濃縮乾固後、カラム精製を行うことで化合物7を0.38g得た。
19F NMR (DMSO-d6, 400 MHz) δ: -197.87-198.10.
化合物7 0.121g(0.348 mmol)を脱水ピリジン 5.0 mLに溶解後、4-メチルペンタノイルクロリド 0.105mL(0.767 mmol)を添加し、16時間攪拌した。反応溶液に酢酸エチルと3N HClを加えて分液した後、水洗した。この酢酸エチル層を濃縮乾固した後、カラム精製を行うことで化合物8を0.195g得た。
19F NMR (CDCl3, 400 MHz) δ: -198.27-198.51.
化合物7 0.08g(0.23 mmol)を脱水ピリジン 8.0 mLに溶解後、ヘキサノイルクロリド 0.0694 mL(0.506 mmol)を添加し、16時間攪拌した。反応溶液を濃縮乾固後、カラム精製を行うことで化合物9を0.061g得た。
19F NMR (CDCl3, 400 MHz) δ: -198.26-198.50.
化合物7 0.16g(0.46 mmol)を脱水ピリジン 4.0 mLに溶解後、メトキシアセチルクロリド 0.092 mL(1.01 mmol)を添加し、16時間攪拌した。反応溶液にクロロホルムと3NHClを加えて分液した後、水洗した。このクロロホルム層を濃縮乾固した後、カラム精製を行うことで化合物10を0.11g得た。
19F NMR (CDCl3, 400 MHz) δ: -198.60-198.85.
化合物1 1.26g(2.98 mmol)、2-フルオロアデニン 1.10g(7.18 mmol)を脱水アセトニトリル 10 mLに溶解後、BSA 2.76 mL(8.96 mmol)を添加し、80℃で1時間攪拌した。0℃まで冷却後、トリフルオロメタンスルホン酸トリメチルシリル 1.3 mL(7.18 mmol)を添加して15分攪拌した後、再び80℃まで昇温した後、一晩攪拌した。反応溶液に飽和炭酸水素ナトリウム水溶液とクロロホルムを加えてセライトろ過後分液した。このクロロホルム層を水洗後、濃縮乾固し、カラム精製を行うことで化合物11を0.254g得た。
19F NMR (CDCl3, 400 MHz) δ: -50.46, -197.87-198.13.
19F NMR (DMSO-d6, 400 MHz) δ: -50.40, -199.05-199.22.
化合物12 0.137g(0.477 mmol)を脱水ピリジン 4.0 mLに溶解後、メトキシアセチルクロリド 0.096 mL(1.05 mmol)を添加し、16時間攪拌した。反応溶液に酢酸エチルと3N HClを加えて分液した後、水洗した。この酢酸エチル層を濃縮乾固した後、カラム精製を行うことで化合物13を0.093g得た。
19F NMR (CDCl3, 400 MHz) δ: -50.40, -199.05-199.22.
化合物12 0.102g(0.355 mmol)を脱水ピリジン 3.0 mLに溶解後、4-メチルペンタノイルクロリド 0.112 mL(0.817 mmol)を添加し、16時間攪拌した。反応溶液にクロロホルムと3N HClを加えて分液した後、水洗した。このクロロホルム層を濃縮乾固した後、カラム精製を行うことで化合物14を0.129g得た。
19F NMR (CDCl3, 400 MHz) δ: -50.40, -198.64-198.90.
実施例1の化合物3(1質量部)に対し製剤の副資剤(キシレン:DMF:ソルポール3005X(東邦化学工業株式会社)=4:4:1)(9質量部)を混合し、10%乳剤を作製した。展着剤グラミンS(東洋グリーン株式会社)を10000倍加用した水で所定濃度の希釈液を調製した。薬剤希釈液を各供試作物にスプレーガンにて十分量散布した。
実施例10の化合物13(1質量部)に対し製剤の副資剤(キシレン:DMF:ソルポール3005X(東邦化学工業株式会社)=4:4:1)(9質量部)を混合し、10%乳剤を作製した。展着剤グラミンS(東洋グリーン株式会社)を10000倍加用した水で所定濃度の希釈液を調製した。薬剤希釈液を供試作物にスプレーガンにて十分量散布した。
供試作物への薬剤の散布後、風乾し、供試虫10頭を放虫した。供試虫逃亡を防ぐため植物をカップとナイロンゴースで覆った。6日後の生存虫の数から死亡率を算出し、補正死亡率を、下記式:
補正死亡率(%)=[(無処理区の生存率-処理区の生存率)/無処理区の生存率]×100
に基づいて算出した。
2.5葉期の幼苗に薬剤を散布処理し、いもち病罹病株と一緒に湿室にて8日間置き、病斑の形成面積を計測し、対無処理区比から防除価を、下記式(N):
防除価=100-(処理区の被害/無処理区の被害)×100 (N)
5葉期のイネに薬剤を散布処理し、地際に紋枯病菌(フスマ)をばらまいて湿室にて6日間置いた後、病斑の上昇を計測し、防除価を前記式(N)に基づいて算出した。
第一本葉完全展開期のダイズの初生葉に薬剤を散布処理し、炭疽病菌の胞子懸濁液を噴霧接種して湿室にて7日間置いた。葉上の病斑面積を計測し、防除価を前記式(N)に基づいて算出した。
2葉期のキュウリに薬剤を散布処理し、褐斑病菌の胞子懸濁液を噴霧接種して湿室にて8日間置いた。葉上の病斑面積を計測し、防除価を前記式(N)に基づいて算出した。
Claims (8)
- R1及びR2が、それぞれ独立して、水素、又はR3CO-である、請求項1に記載の有害生物防除組成物。
- R3が、1個以上の置換基を有していてもよいアルキル基である、請求項1又は2に記載の有害生物防除組成物。
- Xが、フッ素、塩素、又は臭素である、請求項1~3のいずれか一項に記載の有害生物防除組成物。
- Zが、フッ素である、請求項1~4のいずれか一項に記載の有害生物防除組成物。
- 前記有害生物が、植物に対する病害虫又は病原菌である、請求項1~5のいずれか一項に記載の有害生物防除組成物。
- 前記植物が、イネ科植物、アブラナ科植物、ウリ科植物、及びマメ科植物からなる群より選択される少なくとも一種である、請求項6に記載の有害生物防除組成物。
- 植物に直接施用する、又は植物を栽培する土壌に施用するための、請求項1~7のいずれか一項に記載の有害生物防除組成物。
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