JP4875608B2 - 殺虫性n−置換スルホキシイミン類 - Google Patents
殺虫性n−置換スルホキシイミン類 Download PDFInfo
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- JP4875608B2 JP4875608B2 JP2007507515A JP2007507515A JP4875608B2 JP 4875608 B2 JP4875608 B2 JP 4875608B2 JP 2007507515 A JP2007507515 A JP 2007507515A JP 2007507515 A JP2007507515 A JP 2007507515A JP 4875608 B2 JP4875608 B2 JP 4875608B2
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- Prior art keywords
- methyl
- compound
- insecticides
- solution
- chloro
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- -1 N-substituted sulfoximines Chemical class 0.000 title claims description 107
- 230000000749 insecticidal effect Effects 0.000 title description 15
- 150000001875 compounds Chemical class 0.000 claims description 102
- 239000000203 mixture Substances 0.000 claims description 67
- 241000238631 Hexapoda Species 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 230000002779 inactivation Effects 0.000 claims 1
- 239000002917 insecticide Substances 0.000 description 61
- 239000000243 solution Substances 0.000 description 57
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 56
- 239000002904 solvent Substances 0.000 description 42
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- 241000196324 Embryophyta Species 0.000 description 35
- 239000000460 chlorine Substances 0.000 description 33
- 238000012360 testing method Methods 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 241000894007 species Species 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000003921 oil Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- XQOSHWPKADMSKX-UHFFFAOYSA-N C(#N)N=[SH2]=O Chemical class C(#N)N=[SH2]=O XQOSHWPKADMSKX-UHFFFAOYSA-N 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 17
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 17
- 239000002585 base Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000003556 assay Methods 0.000 description 15
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 125000005555 sulfoximide group Chemical group 0.000 description 14
- 241001124076 Aphididae Species 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 11
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 208000024891 symptom Diseases 0.000 description 11
- 241000254127 Bemisia tabaci Species 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 235000005911 diet Nutrition 0.000 description 10
- 230000037213 diet Effects 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 239000007921 spray Substances 0.000 description 10
- 150000003462 sulfoxides Chemical class 0.000 description 10
- 241001600408 Aphis gossypii Species 0.000 description 9
- 241000255925 Diptera Species 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 8
- 229920001213 Polysorbate 20 Polymers 0.000 description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 8
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 8
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 239000012085 test solution Substances 0.000 description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 7
- 241000238876 Acari Species 0.000 description 6
- 235000013601 eggs Nutrition 0.000 description 6
- 239000000417 fungicide Substances 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 239000011550 stock solution Substances 0.000 description 6
- CLNKMAVOYIQLGX-UHFFFAOYSA-N (6-ethoxypyridin-3-yl)-imino-methyl-oxo-$l^{6}-sulfane Chemical compound CCOC1=CC=C(S(C)(=N)=O)C=N1 CLNKMAVOYIQLGX-UHFFFAOYSA-N 0.000 description 5
- 229920001817 Agar Polymers 0.000 description 5
- 239000008272 agar Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000007866 imination reaction Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000003986 organophosphate insecticide Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000256593 Brachycaudus schwartzi Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241001555556 Ephestia elutella Species 0.000 description 4
- 241000258937 Hemiptera Species 0.000 description 4
- 241000721621 Myzus persicae Species 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000000073 carbamate insecticide Substances 0.000 description 4
- 238000012937 correction Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 4
- 238000003359 percent control normalization Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002728 pyrethroid Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- WSGDTZHZIRYZKQ-UHFFFAOYSA-N (6-chloropyridin-3-yl)-imino-methyl-oxo-$l^{6}-sulfane Chemical compound CS(=N)(=O)C1=CC=C(Cl)N=C1 WSGDTZHZIRYZKQ-UHFFFAOYSA-N 0.000 description 3
- INULTQZNLGLSPB-UHFFFAOYSA-N 2-chloro-4-(methoxymethyl)-1,3-thiazole Chemical compound COCc1csc(Cl)n1 INULTQZNLGLSPB-UHFFFAOYSA-N 0.000 description 3
- SKCNYHLTRZIINA-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)pyridine Chemical compound ClCC1=CC=C(Cl)N=C1 SKCNYHLTRZIINA-UHFFFAOYSA-N 0.000 description 3
- SFHWEYFDHRIONH-UHFFFAOYSA-N 2-chloro-5-(iodomethyl)pyridine Chemical compound ClC1=CC=C(CI)C=N1 SFHWEYFDHRIONH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 206010061217 Infestation Diseases 0.000 description 3
- 239000002169 Metam Substances 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
- 208000005374 Poisoning Diseases 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000021523 carboxylation Effects 0.000 description 3
- 238000006473 carboxylation reaction Methods 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000007333 cyanation reaction Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 125000005638 hydrazono group Chemical group 0.000 description 3
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 3
- 239000002949 juvenile hormone Chemical class 0.000 description 3
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229960002523 mercuric chloride Drugs 0.000 description 3
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 3
- 238000006396 nitration reaction Methods 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
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- 231100000572 poisoning Toxicity 0.000 description 3
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- 239000005077 polysulfide Substances 0.000 description 3
- 229920001021 polysulfide Polymers 0.000 description 3
- 150000008117 polysulfides Polymers 0.000 description 3
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- GLBQVJGBPFPMMV-UHFFFAOYSA-N sulfilimine Chemical compound S=N GLBQVJGBPFPMMV-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- CXBMCYHAMVGWJQ-CABCVRRESA-N (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-CABCVRRESA-N 0.000 description 2
- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 2
- RLLPVAHGXHCWKJ-MJGOQNOKSA-N (3-phenoxyphenyl)methyl (1r,3s)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-MJGOQNOKSA-N 0.000 description 2
- VBFHDCVPFKGJBG-UHFFFAOYSA-N (6-chloropyridin-3-yl)methyl-imino-methyl-oxo-$l^{6}-sulfane Chemical compound CS(=N)(=O)CC1=CC=C(Cl)N=C1 VBFHDCVPFKGJBG-UHFFFAOYSA-N 0.000 description 2
- CFRPSFYHXJZSBI-DHZHZOJOSA-N (E)-nitenpyram Chemical compound [O-][N+](=O)/C=C(\NC)N(CC)CC1=CC=C(Cl)N=C1 CFRPSFYHXJZSBI-DHZHZOJOSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 2
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- HQRZFRSRCUTJSZ-UHFFFAOYSA-N 2-(6-chloropyridin-3-yl)propanenitrile Chemical compound N#CC(C)C1=CC=C(Cl)N=C1 HQRZFRSRCUTJSZ-UHFFFAOYSA-N 0.000 description 2
- DRPAFECWIBKIAL-UHFFFAOYSA-N 2-(6-chloropyridin-3-yl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=C(Cl)N=C1 DRPAFECWIBKIAL-UHFFFAOYSA-N 0.000 description 2
- MPUUPHNZUMFOSI-UHFFFAOYSA-N 2-(benzylamino)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1NCC1=CC=CC=C1 MPUUPHNZUMFOSI-UHFFFAOYSA-N 0.000 description 2
- RSRKMTOWZOZSBF-UHFFFAOYSA-N 2-[(6-chloropyridin-3-yl)methyl]-2-methylpropanedioic acid Chemical compound OC(=O)C(C(O)=O)(C)CC1=CC=C(Cl)N=C1 RSRKMTOWZOZSBF-UHFFFAOYSA-N 0.000 description 2
- RHWVXAOTBJLWPC-UHFFFAOYSA-N 2-chloro-5-(iodomethyl)-1,3-thiazole Chemical compound ClC1=NC=C(CI)S1 RHWVXAOTBJLWPC-UHFFFAOYSA-N 0.000 description 2
- GKQDGTBDVTVIDS-UHFFFAOYSA-N 2-chloro-5-methylsulfanylpyridine Chemical compound CSC1=CC=C(Cl)N=C1 GKQDGTBDVTVIDS-UHFFFAOYSA-N 0.000 description 2
- SQABZLUHKYJGNF-UHFFFAOYSA-N 2-ethoxy-5-methoxypyridine Chemical compound COC=1C=NC(=CC1)OCC SQABZLUHKYJGNF-UHFFFAOYSA-N 0.000 description 2
- UXXLFUVYILHKLO-UHFFFAOYSA-N 2-methoxyethylmercury Chemical compound COCC[Hg] UXXLFUVYILHKLO-UHFFFAOYSA-N 0.000 description 2
- MSURRVLVTLHSGH-UHFFFAOYSA-N 3-(6-chloropyridin-3-yl)-2-methylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=C(Cl)N=C1 MSURRVLVTLHSGH-UHFFFAOYSA-N 0.000 description 2
- PEAOEIWYQVXZMB-UHFFFAOYSA-N 5-bromo-2-chloropyridine Chemical compound ClC1=CC=C(Br)C=N1 PEAOEIWYQVXZMB-UHFFFAOYSA-N 0.000 description 2
- 239000005660 Abamectin Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 241000256118 Aedes aegypti Species 0.000 description 2
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- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
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- WRPIRSINYZBGPK-UHFFFAOYSA-N quinoxyfen Chemical compound C1=CC(F)=CC=C1OC1=CC=NC2=CC(Cl)=CC(Cl)=C12 WRPIRSINYZBGPK-UHFFFAOYSA-N 0.000 description 1
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- YGBMMMOLNODPBP-GWGZPXPZSA-N s-ethyl (2e,4e)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienethioate Chemical compound CCSC(=O)\C=C(/C)\C=C\CC(C)CCCC(C)(C)OC YGBMMMOLNODPBP-GWGZPXPZSA-N 0.000 description 1
- NMFAMPYSJHIYMR-UHFFFAOYSA-N s-ethyl n-[3-(dimethylamino)propyl]carbamothioate;hydrochloride Chemical compound [Cl-].CCSC(=O)NCCC[NH+](C)C NMFAMPYSJHIYMR-UHFFFAOYSA-N 0.000 description 1
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 description 1
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- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
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- 230000002588 toxic effect Effects 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
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- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
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- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical class C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
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- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
-
- 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
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Description
XはNO2、CN又はCOOR4を表し;
Lは単結合を表すか又はR1、S及びLは一緒になって5員又は6員環を表し;
R1はメチル又はエチルを表し;
R2及びR3は独立して水素、メチル、エチル、フルオロ、クロロ又はブロモを表し;
nは0〜3の整数であり;
Yは、n=0〜3であり且つLが単結合を表す場合には6−ハロピリジン−3−イル、6−(C1−C4)アルキルピリジン−3−イル、6−(C1−C4)アルコキシピリジン−3−イル、2−クロロチアゾール−4−イル、又は3−クロロイソオキサゾール−5−イルを表し、あるいはYは、n=0〜1であり且つR1、S及びLが一緒になって5員又は6員環を表す場合には水素、C1−C4アルキル、フェニル、6−ハロピリジン−3−イル、6−(C1−C4)アルキルピリジン−3−イル、6−(C1−C4)アルコキシピリジン−3−イル、2−クロロチアゾール−4−イル、又は3−クロロイソオキサゾール−5−イルを表し;且つ
R4はC1−C3アルキルを表す〕
で示される化合物に関する。
(1)XがNO2又はCN、最も好ましくはCNである式(I)の化合物。
(2)R1、S及びLが一緒になって標準的な5員環を表し、n=1であり且つYが6−クロロピリジン−3−イルを表す、すなわち構造
(3)R1、S及びLが一緒になって標準的な5員環を表し且つn=0である、すなわち構造
(4)R1がCH3を表し、Lが単結合を表し且つYが6−クロロピリジン−3−イルを表す、すなわち構造
を有する式(I)の化合物。
スキームA
スキームB
スキームC
スキームD
スキームE
スキームF
スキームG
スキームH
スキームI
実施例I. [3−(6−クロロピリジン−3−イル)−2−メチルプロピル](メチル)オキシド−λ 4 −スルファニリデンシアナミド(2)
B)2−エトキシ−5−(メチルスルホンイミドイル)ピリジン
表2の同定された化合物は、上記の実施例で例証した方法を使用して製造し、また該化合物はワタアブラムシ、モモアカアブラムシ、タバコガ、シロイチモジヨトウ、ショウジョウバエ、蚊、タバココナジラミ及びコロラドハムシに対して以下に記載の方法を使用して試験した。
CA50は、茎葉散布試験でのワタアブラムシに対する50ppmでの防除率%を示す。
CEW50は、食餌試験でのタバコガに対する50μg/cm2での死虫率%を示す。
BAW50は、食餌試験でのシロイチモジヨトウに対する50μ/cm2での死虫率%を示す。
BAW SYMは、注入試験でのシロイチモジヨトウに対する10μg/幼虫での中毒症状を示す%を示す。
FF SYMは、食餌試験でのショウジョウバエに対する25μg/cm2での中毒症状を示す%を示す。
FF25は、食餌試験でのショウジョウバエに対する25μg/cm2での死虫率%を示す。
YFM26は、浸漬試験でのワネッタイシマカに対する26ppmでの防除率%を示す。
SPW200は、茎葉散布試験でのタバココナジラミに対する200ppmでの防除率%を示す。
CPB50は、茎葉散布試験でのコロラドハムシ対する50ppmでの防除率%を示す。
十分に大きくなった子葉を有するカボチャを、植物当たり1枚の子葉に刈り込み、化学物質の施用の1日前にワタアブラムシ(無翅成虫及び幼虫)を寄生させた。適切な寄生(植物当たりアブラムシ約30〜70匹)を確保するために、化学物質の施用の前に各植物を調べた。化合物(3mg)を3mLのアセトン:メタノール(50:50)溶媒に溶解し、1000ppmの原液を調製した。次いで、原液を0.025%のTween 20(H2O溶液)で希釈して、200ppm及び50ppmの噴霧溶液を調製した。携帯用のDevilbiss噴霧器を使用して、噴霧溶液をカボチャの子葉の両側に流出するまで施用した。各化合物のそれぞれの濃度について4個の植物(4反復)を使用した。対照植物(溶媒対照標準)には0.025%のTween20だけを噴霧した。処理植物は、各植物について生存アブラムシの数を記録する前に、保持室で約23℃及び40%RHで3日間保持した。殺虫活性は、アボット(Abbott)の補正式を使用して補正防除率%で測定し、表2に示した:
補正防除率%=100*(X−Y)/X
(式中、X=溶媒対照標準植物の生存アブラムシの数であり、
Y=処理植物の生存アブラムシの数である)
3インチポットで育てた2〜3枚の小さな(3〜5cm)の本葉を有するキャベツの苗を、試験基材として使用した。この苗に、化学物質の施用の2〜3日前に、20〜50匹のモモアカアブラムシ(無翅成虫及び幼虫)を寄生させた。それぞれの試験に4本の苗を使用した。5mgの試験化合物を5mLのアセトン:メタノール(50:50)溶媒に溶解した。次いで、得られた溶液を0.025%のTween20(H2O溶液)で希釈して、0.012ppm、0.049ppm、0.195ppm、0.78ppm、3.13ppm、12.5ppm及び/又は50ppmの噴霧溶液を調製した。携帯用Devilbiss噴霧器を、溶液をキャベツの葉の両側に流出するまで噴霧するのに使用した。対照植物(溶媒対照標準)には0.025%のTween20だけを噴霧した。処理植物は、評価の前に保持室で約23℃及び40%RHで3日間保持した。評価は、顕微鏡の下で植物当たりの生存アブラムシの数を数えることによって行った。殺虫活性は、アボット(Abbott)の補正式を使用することによって測定した:
補正防除率%=100*(X−Y)/X
(式中、X=溶媒対照標準植物の生存アブラムシの数であり、
Y=処理植物の生存アブラムシの数である)
これらのランダウンアッセイから得られた補正防除値%を表4に示す。
食餌アッセイは、128ウエルプラスチックトレイで行った。試験溶液を調製するために、試験化合物を2mLのアセトン:水(9:1)に2000ppmで配合した。得られた試験溶液の50μlの容量を、128ウエルプラスチックトレイの各ウエルの1mLの鱗翅目食餌(Southland Multi-Species Lepidopteran Diet)の表面にピペットで移した。それぞれの昆虫種に対するそれぞれの処理に8個のウエル(8反復)を使用した。この施用量は、50μg/cm2に相当した。溶媒を風乾したら直ちに各ウエルの処理食餌の上に、2齢タバコガ又はシロイチモジヨトウ幼虫を置いた。処理食餌及び幼虫をいれたトレイに、粘着透明シートで覆いをし、成育室に25℃、50〜55%RH、及び16時間照明:8時間暗黒で保持した。観察は、処理及び寄生後5日目に行った。死んだ昆虫の数を、表2に示す死虫率に換算した。
%死虫率=100*X/Y
〔式中、X=死んだ昆虫の数であり、
Y=試験した昆虫の総数(=8)である〕
2mgの工業グレードの化合物を100μlのジメチルスルホキシド又はアセトンに溶解することによって、試験溶液を調製した。各4齢シロイチモジヨトウ幼虫に、ハミルトン(Hamilton)10μl 331/2ゲージ注射器を使用して0.5μl(幼虫当たり試験化合物10μg)の溶液を注射した。試験溶液を、幼虫の外皮の真下の腹部に、昆虫の体の長軸に平行に注射針の長軸で注射した。有効性を確実にするために、溶媒ブランク及び未処理プレートを各試験に含めた。それぞれの処理に6匹の幼虫を使用した。注射した幼虫をそれぞれ、少量の鱗翅目食餌(Southland Multi-Species Lepidopteran Diet製)を有する6ウエルポリスチレンプレートのウエルに置いた。プレートを実験室内で室温で保ち、1時間、24時間及び48時間で評価した。中毒症状をそれぞれの時点で観察した。症状を示す幼虫の数を、症状提示(Show Symtoms)%に換算した。
症状提示%=100*X/Y
〔式中、X=症状を示す幼虫の数であり、
Y=試験した幼虫の総数(=6)である〕
1時間の観察から得られた結果(症状提示%)を表2に示す。
24ウエルを有するポリスチレンプレートを、1000mLの10%ショ糖溶液中に20gの寒天を含有する寒天溶液約300μlで満たした。緑色又は黄色の食品着色料を、消化された際にその色がハエの腹部で目に見える(消化の観察の指標を与える)ように、寒天溶液に加えた。処理の前に、1.5cm濾紙ディスクをそれぞれ、ウエルの固化した寒天層の上に置いた。試験溶液は、500μlのアセトン:水(2:1)溶媒を2mgの工業グレードの化合物に加え、次いで追加の500μlの10%ショ糖溶液を加えて最終濃度2000ppmを得ることによって調製した。溶媒ブランクについては、500μlのアセトン:水(2:1)溶媒を500μlの10%ショ糖溶液に加えた。配合した2000ppm溶液の25μlの容量を、各ウエルの濾紙の上にピペットで移した(25μg/cm2に相当した)。各化合物について4ウエル(4反復)を使用した。次いで、プレートをドラフトの中に30〜45分間置いて溶媒を蒸発させた。供試ハエを冷蔵庫に10〜15分間置き、氷の上に保持したガラス皿の上に移した。冷却されたハエを、ラクダの毛のブラシを有する処理プレートに移した。平均して5〜8匹のハエを各ウエルに使用した。プレートを、ハエを寄生させた直後に蓋をし、実験室で室温で保った。4時間目に中毒症状について観察を行い、48時間目に死虫率%を記録した。症状を示す幼虫の数を、症状提示(Show Symtoms)%に換算し、死んだハエの数を%死虫率に換算した。
症状提示%=100*X/Y
〔式中、X=症状を示すハエの数であり、
Y=試験したハエの総数である〕
%死虫率=100*X/Y
〔式中、X=死んだハエの数であり、
Y=試験したハエの総数である〕
結果を表2に示す。
この試験は、ネッタイシマカの幼虫に対して接触及び消化による化合物の殺虫活性を評価するために計画した。96ウエルを有するマイクロタイタープレートを、ジメチルスルホキシド中の配合化合物を4000ppm濃度で用いて処理した。Tomtecロボット装置を使用して、各配合実験溶液1.5μlをプレートの各ウエルに分注した。各化合物を6個のウエルに施用した(6反復)。施用後に、蚊の幼虫(孵化後3時間齢)を0.4%の蚊の餌(醸造酵母:肝臓粉末=1:3)を含有する水に懸濁し、ウエルに移した。Labsystems製のマルチドロップロボット装置を使用して、5〜8匹の幼虫を有する前記水溶液230μlを処理プレートの各ウエルに分注した。最終試験濃度は約26ppmであった。寄生させた後に、プレートを、蚊が逃げることを可能にする適合透明プラスチック製の蓋でを覆った。寄生させたプレートを、顕微鏡下で調べる前に、インキュベーターに22℃で72時間保持した。殺虫活性は、各複製について防除100%(全て死んだ)又は防除0%(効果がない)として記録した。結果を表2に示す。
この試験は、タバココナジラミの卵及び/又は幼体幼虫が大きな幼虫に成長することができる能力を測定するために計画した。1枚又は2枚の大きくなりつつある本葉の成長期のワタの苗を、最初の本葉だけが残るように刈り込んだ(子葉もまた取り除いた)。この植物に、植物をコロニー保全植物の隣に2日又は3日間保持することによって、タバココナジラミ卵を予め寄生させた。寄生させた植物を、殺虫剤試験で使用する前に、同様の卵の密集状態の存在について注意深く調べた。2000ppmの試験化合物の原液をアセトン:水(9:1)中で調製した。次いで、1mLの原液を9mLの0.025%Tween 20(水溶液)で希釈することによって200ppm噴霧溶液を調製した。試験溶液を、携帯型Devilbiss噴霧器を用いて、ワタの葉の両側に流出するまで噴霧した。各化合物について4本の植物(4反復)を使用した。対照植物(溶媒対照標準)は、9%アセトンを含有する0.025%Tween20を噴霧した。処理植物を、評価する前に保全室に約23℃及び40%RHで13日又は14日間保持した。化合物の効果を評価するために、処理したワタの葉の下面の1平方インチの面積に生存する大きな幼虫の数を、顕微鏡で数えた。殺虫活性は、アボット(Abbott)の補正式を使用して補正防除率%で測定し、表2に示した:
補正防除率%=100*(X−Y)/X
(式中、X=溶媒対照標準植物の生存する大きな幼虫の数であり、
Y=処理植物の生存する大きな幼虫の数である)
3枚又は4枚の大きくなりつつある葉の成長期のトマトの苗を使用した。2000ppmの試験化合物の原液をアセトン:水(9:1)中で調製した。次いで、0.5mLの原液を18.5mLの0.025%Tween20(水溶液)で希釈することによって50ppm噴霧溶液を調製した。試験溶液を、携帯型Devilbiss噴霧器を用いて、植物の表面全体に流出するまで噴霧した。各化合物について、4本の植物(4反復)を使用した。対照植物(溶媒対照標準)は、2.25%アセトンを含有する0.025%Tween20を噴霧した。処理植物を、植物の上部(2又は3枚の葉を有する)を切り取る前に実験室内で約3時間保持して乾燥させ、底に約10mLの固化した1%寒天を入れた10×2.5cmのペトリ皿の中に置いた。2齢又は3齢の幼虫5匹を、処理した植物組織上に置き、ペトリ皿を覆い、インキュベーター中に25℃で保持した。処理後5日目に、各皿の生存幼虫の数を数えることによって、殺虫活性を評価した。補正防除率%をアボット(Abbott)の補正式を使用して算出し、表2に示した:
補正防除率%=100*(X−Y)/X
(式中、X=溶媒対照標準植物の生存幼虫の数であり、
Y=処理植物の生存幼虫の数である)
本発明の化合物は昆虫の防除に有用である。従って、本発明はまた、昆虫阻害量の式(I)の化合物を昆虫の生息場所に施用することからなる昆虫の阻害方法に関する。
鱗翅目 − ヒリオチス(Heliothis)種、ヘリコヴェルパ(Helicoverpa)種、スポドプテラ(Spodoptera)種、アメリカキヨトウ(Mythimna unipuncta)、タマナヤガ(Agrotis ipsilon)、エアリアス種(Earias)種、ユーキソア・アウキシリアリス(Euxoa auxiliaris)、イラクサギンウワバ(Trichoplusia ni)、アンチカルシア・ゲムマタリス(Anticarsia gemmatalis)、ラキプルシア・ヌ(Rachiplusia nu)、コナガ(Plutella xylostella)、チロ(Chilo)種、サンカメイガ(Scirpophaga incertulas)、イネヨトウ(Sesamia inferens)、コブノメイガ(Cnaphalocrocis medinalis)、ヨーロッパアワノメイガ(Ostrinia nubilalis)、コドリンガ(Cydia pomonella)、モモシンクイガ(Carposina niponensis)、リンゴコカクモンハマキ(Adoxophyes orana)、リンゴシロモンハマキ(Archips argyrospilus)、トビハマキ(Pandemis heparana)、エピノチア・アポレマ(Epinotia aporema)、ブドウホソマキ(Eupoecilia ambiguella)、ホソバヒメハマキ(Lobesia botrana)、ブドウヒメハマキ(Polychrosis viteana)、ワタアカミムシ(Pectinophora gossypiella)、モンシロチョウ(Pieris rapae)、フィロノリクテル(Phyllonorycter)種、ロイコプテラ・マリフォリエラ(Leucoptera malifoliella)、ミカンハモグリガ(Phyllocnisitis citrella);
甲虫目 − ディアブロチカ(Diabrotica)種、コロラドハムシ(Leptinotarsa decemlineata)、イネクビボソハムシ(Oulema oryzae)、ワタミハナゾウムシ(Anthonomus grandis)、イネミズゾウムシ(Lissorhoptrus oryzophilus)、アグリオテス(Agriotes)種、メラノツス・コムニス(Melanotus communis)、マメコガネ(Popillia japonica)、シクロセファラ(Cyclocephala)種、トゥボリウム(Tribolium)種。
同翅目 − アブラムシ(Aphis)種、モモアカアブラムシ(Myzus persicae)、ロパロシウム(Rhopalosiphum)種、オオバコアブラムシ(Dysaphis plantaginea)、トキソプテラ(Toxoptera)種、チューリップヒゲナガアブラムシ(Macrosiphum euphorbiae)、ジャガイモヒゲナガアブラムシ(Aulacorthum solani)、シトビオン・アヴェナエ(Sitobion avenae)、ムギウスイロアブラムシ(Metopolophium dirhodum)、ムギミドリアブラムシ(Schizaphis graminum)、ブラキコルス・ノキウス(Brachycolus noxius)、ネホレティックス(Nepholettix)種、トビイロウンカ(Nilaparvata lugens)、セジロウンカ(Sogatella furcifera)、ヒメトビウンカ(Laodelphax striatellus)、タバココナジラミ(Bemisia tabaci)、オンシツコナジラミ(Trialeurodes vaporariorum)、アレウロデス・プロレテラ(Aleurodes proletella)、ウーリーコナジラミ(Aleurothrixus floccosus)、ナシマルカイガラムシ(Quadraspidiotus perniciosus)、ヤノネカイガラムシ(Unaspis yanonensis)、ルビーロウカイガラムシ(Ceroplastes rubens)、アカマルカイガラムシ(Aonidiella aurantii)
半翅目 − リグス(Lygus)種、チャイロカメムシ(Eurygaster maura)、ミナミアオカメムシ(Nezara viridula)、ピエゾドルス・グイルディング(Piezodorus guildingi)、ヘリカメムシ(Leptocorisa varicomis)
総翅目 − ミカンキイロアザミウマ(Frankliniella occidentalis)、アザミウマ(Thrips)種、チャノキイロアザミウマ(Scirtothrips dorsalis)
シロアリ目 − ミゾガシラシロアリ(Reticulitermes flavipes)、イエシロアリ(Coptotermes formosanus)
直翅目 − チャバネゴキブリ(Blattella germanica)、トウヨウゴキブリ(Blatta orientalis)、ケラ(Gryllotalpa)種。
双翅目 − ハモグリバエ(Liriomyza)種、イエバエ(Musca domestica)、ヤブカ(Aedes)種、イエカ(Culex)種、ハマダラカ(Anopheles)種。
膜翅目 − アルゼンチンアリ(Iridomyrmex humilis)、ソレノプシス(Solenopsis)種、イエヒメアリ(Monomorium pharaonis)、アッタ(Atta)種、ポゴノミルメクス(Pogonomyrmex)種、カンポノツス(Camponotus)種。
ノミ目 − クテノファリセス(Ctenophalides)種、ヒトノミ(Pulex irritans)
ダニ目 − ハダニ(Tetranychus)種、パノニクス(Panonychus)種、Eotetranychus carpini、ミカンサビダニ(Phyllocoptfuta oleivora)、アクルス・ペレカッシイ(Aculus pelekassi)、ヒメハダニ(Brevipalpus phoenicis)、ウシダニ(Boophilus)種、アメリカイヌカクマダニ(Dermacentor variabilis)、クリイロコイタマダニ(Rhipicephalus sanguineus)、アメリカキララマダニ(Amblyomma americanum)、マダニ(Ixodes)種、ヒゼンダニ(Notoedres cati)、サピコプテス・スカビエイ(Sarcoptes scabiei)、デルマトファゴイデス(Dermatophagoides)種
が挙げられるが、これらに限定されない。
本発明の化合物は、本発明の重要な実施形態であり且つ本発明の化合物と植物学的に許容し得る不活性担体を含む組成物の形態で施用される。本組成物は、施用のために水に分散される濃厚製剤であるか、又はさらに処理することなく施用される粉剤又は粒剤である。本組成物は、農芸化学技術において慣用される方法及び処方に従って製造されるが、本発明の化合物が該組成物中に存在するために新規であり且つ重要である。しかし、本組成物の処方の幾つかの説明が、農業化学者が所望の組成物を容易に製造することができることを確実にするために示されるであろう。
Claims (8)
- 式(I)
XはNO2、CN又はCOOR4を表し;
Lは単結合を表すか又はR1、S及びLは一緒になって5員又は6員環を表し;
R1はメチル又はエチルを表し;
R2及びR3は独立して水素、メチル、エチル、フルオロ、クロロ又はブロモを表し;
nは0〜3の整数であり;
Yは、n=0〜3であり且つLが単結合を表す場合には6−ハロピリジン−3−イル、6−(C1−C4)アルキルピリジン−3−イル、6−(C1−C4)アルコキシピリジン−3−イル、2−クロロチアゾール−4−イル、又は3−クロロイソオキサゾール−5−イルを表し、あるいはYは、n=0〜1であり且つR1、S及びLが一緒になって5員又は6員環を表す場合にはC 1−C4アルキル、フェニル、6−ハロピリジン−3−イル、6−(C1−C4)アルキルピリジン−3−イル、6−(C1−C4)アルコキシピリジン−3−イル、2−クロロチアゾール−4−イル、又は3−クロロイソオキサゾール−5−イルを表し;且つ
R4はC1−C3アルキルを表す〕
で示される化合物。 - XがNO2又はCNを表す、請求項1に記載の化合物。
- 式
XはNO2、CN又はCOOR4を表し;
Yは6−ハロピリジン−3−イル、6−(C1−C4)アルキルピリジン−3−イル、6−(C1−C4)アルコキシピリジン−3−イル、2−クロロチアゾール−4−イル、又は3−クロロイソオキサゾール−5−イルを表し;
R2及びR3は独立して水素、メチル、エチル、フルオロ、クロロ又はブロモを表し;且つ
R4はC1−C3アルキルを表す〕
を有する、請求項1に記載の化合物。 - 式
XはNO2、CN又はCOOR4を表し;
R2及びR3は独立して水素、メチル、エチル、フルオロ、クロロ又はブロモを表し;且つ
R4はC1−C3アルキルを表す)
を有する、請求項3に記載の化合物。 - 式
XはNO2、CN又はCOOR4を表し;
YはC 1−C4アルキル又はフェニルを表し;且つ
R4はC1−C3アルキルを表す)
を有する、請求項1に記載の化合物。 - 式
XはNO2、CN又はCOOR4を表し;
R2及びR3は独立して水素、メチル、エチル、フルオロ、クロロ又はブロモを表し;
R4はC1−C3アルキルを表し;且つ
nは1〜3の整数を表す)
を有する、請求項1に記載の化合物。 - 請求項1から6のいずれか1項に記載の化合物を、植物学的に許容し得る担体と組み合わせて含有する昆虫防除用組成物。
- 防除が望まれる場所に昆虫不活性化量の請求項1から6のいずれか1項に記載の化合物を施用することからなる昆虫の防除方法。
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US56062804P | 2004-04-08 | 2004-04-08 | |
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PCT/US2005/011852 WO2006060029A2 (en) | 2004-04-08 | 2005-04-08 | Insecticidal n-substituted sulfoximines |
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US20100076032A1 (en) | 2010-03-25 |
WO2006060029A3 (en) | 2006-08-31 |
WO2006060029A2 (en) | 2006-06-08 |
CN101648906A (zh) | 2010-02-17 |
KR101151932B1 (ko) | 2012-06-01 |
US7897782B2 (en) | 2011-03-01 |
BRPI0509695A (pt) | 2007-10-09 |
MXPA06011589A (es) | 2006-12-20 |
BRPI0509695B1 (pt) | 2014-12-02 |
US20100063136A1 (en) | 2010-03-11 |
US20100056578A1 (en) | 2010-03-04 |
US7795456B2 (en) | 2010-09-14 |
ES2611018T3 (es) | 2017-05-04 |
KR20070022674A (ko) | 2007-02-27 |
BRPI0509695B8 (pt) | 2022-06-28 |
CA2558647A1 (en) | 2006-06-08 |
JP2007532568A (ja) | 2007-11-15 |
CA2558647C (en) | 2013-05-28 |
EP1732895A2 (en) | 2006-12-20 |
CN1942442B (zh) | 2012-10-31 |
US7829719B2 (en) | 2010-11-09 |
US20050228027A1 (en) | 2005-10-13 |
AU2005310314B2 (en) | 2011-07-21 |
ZA200607292B (en) | 2008-05-28 |
EP1732895B1 (en) | 2016-11-16 |
US20100056579A1 (en) | 2010-03-04 |
US7834188B2 (en) | 2010-11-16 |
CN101648906B (zh) | 2012-07-11 |
CN1942442A (zh) | 2007-04-04 |
US7678920B2 (en) | 2010-03-16 |
HK1104285A1 (en) | 2008-01-11 |
AU2005310314A1 (en) | 2006-06-08 |
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