JP5587787B2 - 殺虫化合物 - Google Patents
殺虫化合物 Download PDFInfo
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- JP5587787B2 JP5587787B2 JP2010538439A JP2010538439A JP5587787B2 JP 5587787 B2 JP5587787 B2 JP 5587787B2 JP 2010538439 A JP2010538439 A JP 2010538439A JP 2010538439 A JP2010538439 A JP 2010538439A JP 5587787 B2 JP5587787 B2 JP 5587787B2
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- Prior art keywords
- formula
- methyl
- compound
- trifluoromethyl
- independently
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 254
- 230000000749 insecticidal effect Effects 0.000 title claims description 16
- -1 pyrazoyl Chemical group 0.000 claims description 130
- 229910052760 oxygen Inorganic materials 0.000 claims description 116
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 109
- 239000001301 oxygen Substances 0.000 claims description 109
- 239000000203 mixture Substances 0.000 claims description 85
- 239000001257 hydrogen Substances 0.000 claims description 68
- 229910052739 hydrogen Inorganic materials 0.000 claims description 68
- 150000002431 hydrogen Chemical class 0.000 claims description 50
- 229910052736 halogen Inorganic materials 0.000 claims description 43
- 150000002367 halogens Chemical class 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 150000001204 N-oxides Chemical class 0.000 claims description 38
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
- 125000001246 bromo group Chemical group Br* 0.000 claims description 29
- 125000001188 haloalkyl group Chemical group 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
- 241000607479 Yersinia pestis Species 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000001153 fluoro group Chemical group F* 0.000 claims description 18
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 241000244206 Nematoda Species 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
- 230000000895 acaricidal effect Effects 0.000 claims description 9
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 9
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 9
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 8
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 241000237852 Mollusca Species 0.000 claims description 7
- 241000238876 Acari Species 0.000 claims description 6
- 241000238631 Hexapoda Species 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 230000002013 molluscicidal effect Effects 0.000 claims description 5
- 230000004071 biological effect Effects 0.000 claims description 4
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 230000001069 nematicidal effect Effects 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims 1
- 239000005645 nematicide Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 62
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 54
- 238000006243 chemical reaction Methods 0.000 description 54
- 239000011541 reaction mixture Substances 0.000 description 54
- 238000002360 preparation method Methods 0.000 description 46
- 238000005160 1H NMR spectroscopy Methods 0.000 description 44
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 39
- 239000002904 solvent Substances 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 31
- 239000000543 intermediate Substances 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000002585 base Substances 0.000 description 24
- 229910052938 sodium sulfate Inorganic materials 0.000 description 22
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 21
- 235000011152 sodium sulphate Nutrition 0.000 description 21
- 125000001424 substituent group Chemical group 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 20
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 20
- 239000007787 solid Substances 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- 150000001412 amines Chemical class 0.000 description 18
- DCNCUISGPGXEPO-UHFFFAOYSA-N methyl 5-bromo-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC(Br)=C1C1=NOC(C(F)(F)F)(C=2C=C(Cl)C=C(Cl)C=2)C1 DCNCUISGPGXEPO-UHFFFAOYSA-N 0.000 description 18
- 239000000843 powder Substances 0.000 description 17
- KBWVSPGZOPXKRR-UHFFFAOYSA-N 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-2-methylbenzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC(C=2CC(ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)=C1 KBWVSPGZOPXKRR-UHFFFAOYSA-N 0.000 description 16
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
- 229910052794 bromium Inorganic materials 0.000 description 16
- 239000007788 liquid Substances 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 14
- 241000196324 Embryophyta Species 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
- 241000256602 Isoptera Species 0.000 description 10
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
- 239000002917 insecticide Substances 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 239000008187 granular material Substances 0.000 description 9
- 150000002576 ketones Chemical class 0.000 description 9
- 239000004530 micro-emulsion Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000004546 suspension concentrate Substances 0.000 description 9
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- HSVBBRKMHLTVSN-UHFFFAOYSA-N tert-butyl 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-2-methylbenzoate Chemical compound C1=C(C(=O)OC(C)(C)C)C(C)=CC(C=2CC(ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)=C1 HSVBBRKMHLTVSN-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 241000209149 Zea Species 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 235000005822 corn Nutrition 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- BYZLEUFNXHHCPD-UHFFFAOYSA-N methyl 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-2-(trifluoromethyl)benzoate Chemical compound C1=C(C(F)(F)F)C(C(=O)OC)=CC=C1C1=NOC(C(F)(F)F)(C=2C=C(Cl)C=C(Cl)C=2)C1 BYZLEUFNXHHCPD-UHFFFAOYSA-N 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
- HVRPRWJXVGBWAK-UHFFFAOYSA-N 4-(bromomethyl)-2-(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC=C(CBr)C=C1C(F)(F)F HVRPRWJXVGBWAK-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- 241000255925 Diptera Species 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- KZZOEWALRAUCBM-UHFFFAOYSA-N methyl 4-(c-chloro-n-hydroxycarbonimidoyl)-2-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(C(Cl)=NO)C=C1C(F)(F)F KZZOEWALRAUCBM-UHFFFAOYSA-N 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- 239000007800 oxidant agent Substances 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 239000012085 test solution Substances 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- 239000000080 wetting agent Substances 0.000 description 6
- XHVYAPWEVAZVJF-UHFFFAOYSA-N 4-(hydroxymethyl)-2-(trifluoromethyl)benzoic acid Chemical compound OCC1=CC=C(C(O)=O)C(C(F)(F)F)=C1 XHVYAPWEVAZVJF-UHFFFAOYSA-N 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000003337 fertilizer Substances 0.000 description 5
- 239000004009 herbicide Substances 0.000 description 5
- FRLOQUPGGHVRSC-UHFFFAOYSA-N methyl 4-(hydroxyiminomethyl)-2-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(C=NO)C=C1C(F)(F)F FRLOQUPGGHVRSC-UHFFFAOYSA-N 0.000 description 5
- RUDDPYMBSUULPV-UHFFFAOYSA-N methyl 4-(hydroxymethyl)-2-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(CO)C=C1C(F)(F)F RUDDPYMBSUULPV-UHFFFAOYSA-N 0.000 description 5
- CGGGWRDRBMSXOL-UHFFFAOYSA-N methyl 4-formyl-2-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1C(F)(F)F CGGGWRDRBMSXOL-UHFFFAOYSA-N 0.000 description 5
- PGMVAJKHWYOZIA-UHFFFAOYSA-N methyl 5-chloro-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC(Cl)=C1C1=NOC(C(F)(F)F)(C=2C=C(Cl)C=C(Cl)C=2)C1 PGMVAJKHWYOZIA-UHFFFAOYSA-N 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 235000021391 short chain fatty acids Nutrition 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- VMBLIXPKLRBDTA-UHFFFAOYSA-N tert-butyl 4-(hydroxyiminomethyl)-2-methylbenzoate Chemical compound CC1=CC(C=NO)=CC=C1C(=O)OC(C)(C)C VMBLIXPKLRBDTA-UHFFFAOYSA-N 0.000 description 5
- KKSOKTQAWHCIMG-UHFFFAOYSA-N tert-butyl 4-bromo-2-methylbenzoate Chemical compound CC1=CC(Br)=CC=C1C(=O)OC(C)(C)C KKSOKTQAWHCIMG-UHFFFAOYSA-N 0.000 description 5
- AUBIZGDRTQAOGD-UHFFFAOYSA-N tert-butyl 4-formyl-2-methylbenzoate Chemical compound CC1=CC(C=O)=CC=C1C(=O)OC(C)(C)C AUBIZGDRTQAOGD-UHFFFAOYSA-N 0.000 description 5
- 239000004562 water dispersible granule Substances 0.000 description 5
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 4
- IEMWQUAHEWCUGX-UHFFFAOYSA-N 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-2-methyl-n-(3-methylthietan-3-yl)benzamide Chemical compound CC1=CC(C=2CC(ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)=CC=C1C(=O)NC1(C)CSC1 IEMWQUAHEWCUGX-UHFFFAOYSA-N 0.000 description 4
- DTITWJLFGHVOLI-UHFFFAOYSA-N 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-2-methyl-n-[1-oxo-1-(2,2,2-trifluoroacetyl)iminothietan-3-yl]benzamide Chemical compound CC1=CC(C=2CC(ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)=CC=C1C(=O)NC1CS(=O)(=NC(=O)C(F)(F)F)C1 DTITWJLFGHVOLI-UHFFFAOYSA-N 0.000 description 4
- 241000239290 Araneae Species 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 0 CI*C(*)(*C=C)IN(*)C(C(*=*)=**=C(C(C=C(*)*)=O)I)=* Chemical compound CI*C(*)(*C=C)IN(*)C(C(*=*)=**=C(C(C=C(*)*)=O)I)=* 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- 241000258937 Hemiptera Species 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 239000005909 Kieselgur Substances 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
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- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 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
- A01N43/72—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
- A01N43/80—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 1,2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0725219A GB0725219D0 (en) | 2007-12-24 | 2007-12-24 | Insecticidal compounds |
| GB0725219.0 | 2007-12-24 | ||
| GB0813849.7 | 2008-07-29 | ||
| GB0813849A GB0813849D0 (en) | 2008-07-29 | 2008-07-29 | Insecticidal compounds |
| PCT/EP2008/010701 WO2009080250A2 (en) | 2007-12-24 | 2008-12-16 | Insecticidal compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011507813A JP2011507813A (ja) | 2011-03-10 |
| JP2011507813A5 JP2011507813A5 (enExample) | 2014-02-13 |
| JP5587787B2 true JP5587787B2 (ja) | 2014-09-10 |
Family
ID=40404285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010538439A Expired - Fee Related JP5587787B2 (ja) | 2007-12-24 | 2008-12-16 | 殺虫化合物 |
Country Status (38)
Families Citing this family (162)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7449486B2 (en) | 2004-10-19 | 2008-11-11 | Array Biopharma Inc. | Mitotic kinesin inhibitors and methods of use thereof |
| WO2008108448A1 (ja) | 2007-03-07 | 2008-09-12 | Nissan Chemical Industries, Ltd. | イソキサゾリン置換ベンズアミド化合物及び有害生物防除剤 |
| TWI411395B (zh) * | 2007-12-24 | 2013-10-11 | Syngenta Participations Ag | 殺蟲化合物 |
| ES2434734T3 (es) | 2008-08-22 | 2013-12-17 | Syngenta Participations Ag | Compuestos insecticidas |
| KR20110044873A (ko) * | 2008-08-22 | 2011-05-02 | 신젠타 파티서페이션즈 아게 | 살충성 화합물 |
| CA2732217A1 (en) * | 2008-09-04 | 2010-03-11 | Peter Renold | Insecticidal compounds |
| EP2413701A4 (en) | 2009-03-31 | 2012-10-03 | Univ Vanderbilt | SULFONYL-AZETIDIN-3-YL-METHYLAMINE AMIDE ANALOGUES AS GLYT1 INHIBITORS, METHODS OF MAKING THEM AND USE THEREOF IN THE TREATMENT OF PSYCHIATRIC DISORDERS |
| WO2010149506A1 (en) * | 2009-06-22 | 2010-12-29 | Syngenta Participations Ag | Insecticidal compounds |
| JP2013510080A (ja) | 2009-11-06 | 2013-03-21 | バイエル・クロップサイエンス・アーゲー | 殺虫性アリールピロリン化合物 |
| TWI487486B (zh) | 2009-12-01 | 2015-06-11 | Syngenta Participations Ag | 以異唑啉衍生物為主之殺蟲化合物 |
| CN102762543B (zh) | 2010-02-01 | 2016-03-09 | 巴斯夫欧洲公司 | 用于防除动物害虫的取代的酮型异*唑啉化合物和衍生物 |
| EP2536698B1 (en) | 2010-02-17 | 2015-06-10 | Syngenta Participations AG | Isoxazoline derivatives as insecticides |
| JP2013520403A (ja) * | 2010-02-22 | 2013-06-06 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | 殺虫化合物としてのジヒドロフラン誘導体 |
| WO2011104088A1 (en) | 2010-02-25 | 2011-09-01 | Syngenta Participations Ag | Pesticidal mixtures containing isoxazoline derivatives and a fungicide |
| CN102822168B (zh) | 2010-02-25 | 2016-10-26 | 先正达参股股份有限公司 | 制备异恶唑啉衍生物的方法 |
| NZ601446A (en) | 2010-02-25 | 2014-03-28 | Syngenta Participations Ag | Pesticidal mixtures containing isoxazoline derivatives and insecticide or nematoicidal biological agent |
| EP2579723A2 (en) | 2010-06-09 | 2013-04-17 | Syngenta Participations AG | Pesticidal mixtures comprising isoxazoline derivatives |
| TW201211057A (en) | 2010-06-11 | 2012-03-16 | Syngenta Participations Ag | Process for the preparation of dihydropyrrole derivatives |
| DK178277B1 (da) | 2010-06-18 | 2015-10-26 | Novartis Tiergesundheit Ag | Diaryloxazolinforbindelser til bekæmpelse af fiskelus |
| JP2012017289A (ja) | 2010-07-08 | 2012-01-26 | Bayer Cropscience Ag | 殺虫性ピロリン誘導体 |
| WO2012007426A1 (en) | 2010-07-13 | 2012-01-19 | Basf Se | Azoline substituted isoxazoline benzamide compounds for combating animal pests |
| PH12013500164A1 (en) * | 2010-08-05 | 2015-07-08 | Zoetis Services Llc | Isoxazoline derivatives as antiparasitic agents |
| BR112013008063A2 (pt) * | 2010-10-05 | 2016-06-14 | Syngenta Participations Ag | pirrolidin-il-aril-carboxamidas inseticidas |
| CN103282345A (zh) * | 2010-11-03 | 2013-09-04 | 巴斯夫欧洲公司 | 制备取代的异噁唑啉化合物及其前体4-氯-、4-溴-或4-碘苯甲醛肟的方法 |
| JP2014028758A (ja) * | 2010-11-19 | 2014-02-13 | Nissan Chem Ind Ltd | 寄生虫及び衛生害虫防除剤 |
| WO2012080419A1 (en) | 2010-12-15 | 2012-06-21 | Syngenta Participations Ag | Pesticidal mixtures |
| UY33887A (es) * | 2011-02-03 | 2012-09-28 | Syngenta Ltd | Métodos de control de plagas en la soja |
| AR086113A1 (es) * | 2011-04-30 | 2013-11-20 | Abbott Lab | Isoxazolinas como agentes terapeuticos |
| JP6030640B2 (ja) | 2011-05-18 | 2016-11-24 | シンジェンタ パーティシペーションズ アーゲー | アリールチオアセトアミド誘導体をベースとする殺虫化合物 |
| TWI555471B (zh) | 2011-05-31 | 2016-11-01 | 先正達合夥公司 | 包含異唑啉衍生物之殺有害生物混合物 |
| TW201311677A (zh) | 2011-05-31 | 2013-03-16 | Syngenta Participations Ag | 殺蟲化合物 |
| WO2012163948A1 (en) | 2011-05-31 | 2012-12-06 | Syngenta Participations Ag | Pesticidal mixtures including isoxazoline derivatives |
| CN103649070B (zh) * | 2011-07-08 | 2016-05-18 | 先正达参股股份有限公司 | 用于制备硫杂环丁胺的方法 |
| WO2013026929A1 (en) | 2011-08-25 | 2013-02-28 | Syngenta Participations Ag | Dihydropyrrole derivatives as insecticidal compounds |
| WO2013026695A1 (en) | 2011-08-25 | 2013-02-28 | Syngenta Participations Ag | Isoxazoline derivatives as insecticidal compounds |
| WO2013026939A1 (en) | 2011-08-25 | 2013-02-28 | Syngenta Participations Ag | Methods for the control of termites and ants |
| CN103764644A (zh) * | 2011-08-25 | 2014-04-30 | 先正达参股股份有限公司 | 作为杀虫化合物的异噁唑啉衍生物 |
| WO2013026933A1 (en) | 2011-08-25 | 2013-02-28 | Syngenta Participations Ag | Isoxazoline derivatives as insecticidal compounds |
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| BR122018069466B1 (pt) * | 2011-09-13 | 2019-04-02 | Syngenta Participations Ag | Derivados isotiazolina como compostos inseticidas |
| WO2013050301A1 (en) | 2011-10-03 | 2013-04-11 | Syngenta Participations Ag | Enantionselective processes to insecticidal 3-aryl-3-trifluoromethyl-substituted pyrrolidines |
| WO2013050317A1 (en) | 2011-10-03 | 2013-04-11 | Syngenta Limited | Polymorphs of an isoxazoline derivative |
| EP3896058A3 (en) | 2011-10-03 | 2022-01-12 | Syngenta Participations Ag | Enantionselective processes to insecticidal 3-aryl-3-trifluoromethyl-substituted pyrrolidines |
| BR112014007847A2 (pt) | 2011-10-03 | 2017-04-18 | Syngenta Participations Ag | derivados de isoxazolina como compostos inseticidas |
| US9126995B2 (en) | 2011-11-08 | 2015-09-08 | Nissan Chemical Industries, Ltd. | Method for catalytic asymmetric synthesis of optically active isoxazoline compound and optically active isoxazoline compound |
| US20140343085A1 (en) | 2011-11-29 | 2014-11-20 | Novartis Ag | Use of aryl derivatives for controlling ectoparasites |
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| WO2013135674A1 (en) | 2012-03-12 | 2013-09-19 | Syngenta Participations Ag | Insecticidal 2-aryl-acetamide compounds |
| WO2013150052A1 (en) | 2012-04-04 | 2013-10-10 | Intervet International B.V. | Soft chewable pharmaceutical products |
| WO2013190050A1 (en) * | 2012-06-21 | 2013-12-27 | Syngenta Participations Ag | Methods of controlling insects |
| AR091513A1 (es) * | 2012-06-21 | 2015-02-11 | Syngenta Participations Ag | Metodos de control de plagas del suelo |
| WO2014005982A1 (de) | 2012-07-05 | 2014-01-09 | Bayer Cropscience Ag | Insektizide und fungizide wirkstoffkombinationen |
| US9867375B2 (en) | 2012-07-31 | 2018-01-16 | Syngenta Participations Ag | Methods of pest control in soybean |
| US11930816B2 (en) | 2012-08-03 | 2024-03-19 | Syngenta Participations Ag | Methods of pest control in soybean |
| US20150189883A1 (en) | 2012-08-03 | 2015-07-09 | Syngenta Participations Ag | Methods of controlling insects |
| BR112015001979A2 (pt) | 2012-08-03 | 2017-07-04 | Syngenta Participations Ag | métodos de controle de pragas em soja |
| US9320278B2 (en) * | 2012-08-24 | 2016-04-26 | Syngenta Participations Ag | Methods of controlling insects |
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