WO2021082901A1 - Phenylisoxazoline compound and use thereof - Google Patents
Phenylisoxazoline compound and use thereof Download PDFInfo
- Publication number
- WO2021082901A1 WO2021082901A1 PCT/CN2020/120564 CN2020120564W WO2021082901A1 WO 2021082901 A1 WO2021082901 A1 WO 2021082901A1 CN 2020120564 W CN2020120564 W CN 2020120564W WO 2021082901 A1 WO2021082901 A1 WO 2021082901A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- hydrogen
- methyl
- butyl
- haloalkyl
- Prior art date
Links
- -1 Phenylisoxazoline compound Chemical class 0.000 title claims abstract description 162
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 241000196324 Embryophyta Species 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 124
- 239000001257 hydrogen Substances 0.000 claims description 124
- 150000002431 hydrogen Chemical class 0.000 claims description 118
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 84
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 69
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 67
- 239000000460 chlorine Substances 0.000 claims description 62
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 61
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 51
- 229910052801 chlorine Inorganic materials 0.000 claims description 51
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 50
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 47
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 47
- 229910052794 bromium Inorganic materials 0.000 claims description 47
- 239000011737 fluorine Substances 0.000 claims description 47
- 229910052731 fluorine Inorganic materials 0.000 claims description 47
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 45
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 44
- 229910052736 halogen Inorganic materials 0.000 claims description 42
- 150000002367 halogens Chemical class 0.000 claims description 42
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 36
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 32
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 30
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 25
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 22
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 18
- 125000006001 difluoroethyl group Chemical group 0.000 claims description 18
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 17
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 16
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 16
- 125000006006 difluoroethoxy group Chemical group 0.000 claims description 16
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 15
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 15
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 14
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 12
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 claims description 8
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 8
- 125000002873 tetrahydrofuranonyl group Chemical group 0.000 claims description 8
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000006202 diisopropylaminoethyl group Chemical group [H]C([H])([H])C([H])(N(C([H])([H])C([H])([H])*)C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 6
- 125000006603 (C1-C3) alkylaminosulfonyl group Chemical group 0.000 claims description 4
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 4
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 claims description 2
- GCQZRSVHYPEACN-UHFFFAOYSA-N 2-methylideneoxolane Chemical group C=C1CCCO1 GCQZRSVHYPEACN-UHFFFAOYSA-N 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims description 2
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 2
- VQKFNUFAXTZWDK-UHFFFAOYSA-N alpha-methylfuran Natural products CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 abstract description 13
- 239000004009 herbicide Substances 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 5
- 244000058871 Echinochloa crus-galli Species 0.000 abstract description 4
- 240000003307 Zinnia violacea Species 0.000 abstract description 4
- 235000010823 Digitaria sanguinalis Nutrition 0.000 abstract description 2
- 235000010469 Glycine max Nutrition 0.000 abstract description 2
- 240000007594 Oryza sativa Species 0.000 abstract description 2
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 2
- 244000234609 Portulaca oleracea Species 0.000 abstract description 2
- 235000001855 Portulaca oleracea Nutrition 0.000 abstract description 2
- 235000021307 Triticum Nutrition 0.000 abstract description 2
- 244000098338 Triticum aestivum Species 0.000 abstract description 2
- 244000067505 Xanthium strumarium Species 0.000 abstract description 2
- 240000008042 Zea mays Species 0.000 abstract description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 abstract description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 abstract description 2
- 235000005822 corn Nutrition 0.000 abstract description 2
- 235000009566 rice Nutrition 0.000 abstract description 2
- 238000009333 weeding Methods 0.000 abstract description 2
- 240000006995 Abutilon theophrasti Species 0.000 abstract 1
- 244000237956 Amaranthus retroflexus Species 0.000 abstract 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 abstract 1
- 241000309551 Arthraxon hispidus Species 0.000 abstract 1
- 244000201986 Cassia tora Species 0.000 abstract 1
- 235000014552 Cassia tora Nutrition 0.000 abstract 1
- 244000108484 Cyperus difformis Species 0.000 abstract 1
- 244000152970 Digitaria sanguinalis Species 0.000 abstract 1
- 244000062387 Glycine soja Species 0.000 abstract 1
- 241001075721 Hibiscus trionum Species 0.000 abstract 1
- 235000001047 Hibiscus trionum Nutrition 0.000 abstract 1
- 240000003461 Setaria viridis Species 0.000 abstract 1
- 235000002248 Setaria viridis Nutrition 0.000 abstract 1
- 244000061457 Solanum nigrum Species 0.000 abstract 1
- 235000002594 Solanum nigrum Nutrition 0.000 abstract 1
- 244000082735 tidal marsh flat sedge Species 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 0 C*c1c(*)[n](*)nc1-c1c(*)cc(*(C)=C)c(C)c1 Chemical compound C*c1c(*)[n](*)nc1-c1c(*)cc(*(C)=C)c(C)c1 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- ZSSRSUBTIJYIOJ-UHFFFAOYSA-N 2-chloro-5-[4-chloro-1-methyl-5-(trifluoromethyl)pyrazol-3-yl]-4-fluorobenzaldehyde Chemical compound ClC1=C(C(F)(F)F)N(C)N=C1C1=CC(C=O)=C(Cl)C=C1F ZSSRSUBTIJYIOJ-UHFFFAOYSA-N 0.000 description 3
- YOWQWFMSQCOSBA-UHFFFAOYSA-N 2-methoxypropene Chemical compound COC(C)=C YOWQWFMSQCOSBA-UHFFFAOYSA-N 0.000 description 3
- YNQXHQDFBVIEDP-UHFFFAOYSA-N 3-(4-chloro-2-fluoro-5-methylphenyl)-1-methyl-5-(trifluoromethyl)pyrazole Chemical compound C1=C(Cl)C(C)=CC(C2=NN(C)C(=C2)C(F)(F)F)=C1F YNQXHQDFBVIEDP-UHFFFAOYSA-N 0.000 description 3
- WRKFXAOCCNHKDE-UHFFFAOYSA-N 3-(4-chloro-2-fluoro-5-methylphenyl)-5-(trifluoromethyl)-1h-pyrazole Chemical compound C1=C(Cl)C(C)=CC(C2=NNC(=C2)C(F)(F)F)=C1F WRKFXAOCCNHKDE-UHFFFAOYSA-N 0.000 description 3
- UXHCAAKUKLASHB-UHFFFAOYSA-N 4-chloro-3-(4-chloro-2-fluoro-5-methylphenyl)-1-methyl-5-(trifluoromethyl)pyrazole Chemical compound C1=C(Cl)C(C)=CC(C=2C(=C(N(C)N=2)C(F)(F)F)Cl)=C1F UXHCAAKUKLASHB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- CSARJIQZOSVYHA-UHFFFAOYSA-N 2-chloro-4-fluoro-1-methylbenzene Chemical compound CC1=CC=C(F)C=C1Cl CSARJIQZOSVYHA-UHFFFAOYSA-N 0.000 description 2
- 241000219144 Abutilon Species 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- NDPDFKFHZWBICC-UHFFFAOYSA-N CN1C(=C(C(=N1)C2=C(C=C(C(=C2)C=NOCl)Cl)F)Cl)C(F)(F)F Chemical compound CN1C(=C(C(=N1)C2=C(C=C(C(=C2)C=NOCl)Cl)F)Cl)C(F)(F)F NDPDFKFHZWBICC-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- JGWYSVOCJHJVAG-UHFFFAOYSA-N N-[[2-chloro-5-[4-chloro-1-methyl-5-(trifluoromethyl)pyrazol-3-yl]-4-fluorophenyl]methylidene]hydroxylamine Chemical compound CN1C(=C(C(=N1)C2=C(C=C(C(=C2)C=NO)Cl)F)Cl)C(F)(F)F JGWYSVOCJHJVAG-UHFFFAOYSA-N 0.000 description 2
- 235000005775 Setaria Nutrition 0.000 description 2
- 241000232088 Setaria <nematode> Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 2
- YKKPYMXANSSQCA-UHFFFAOYSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-(3-pyrazol-1-ylazetidin-1-yl)methanone Chemical compound N1(N=CC=C1)C1CN(C1)C(=O)C1=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F YKKPYMXANSSQCA-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 229940117975 chromium trioxide Drugs 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- BEWCNXNIQCLWHP-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(C)(C)C BEWCNXNIQCLWHP-UHFFFAOYSA-N 0.000 description 1
- YXYJVFYWCLAXHO-UHFFFAOYSA-N 2-methoxyethyl 2-methylprop-2-enoate Chemical compound COCCOC(=O)C(C)=C YXYJVFYWCLAXHO-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- UKFPAGCSDWQXFT-UHFFFAOYSA-N 3-phenyl-4,5-dihydro-1,2-oxazole Chemical class O1CCC(C=2C=CC=CC=2)=N1 UKFPAGCSDWQXFT-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241001290610 Abildgaardia Species 0.000 description 1
- 240000000321 Abutilon grandifolium Species 0.000 description 1
- XURLYGPRHXPGBN-UHFFFAOYSA-N C1CCC=CC1.COC(=O)C(C)=C Chemical compound C1CCC=CC1.COC(=O)C(C)=C XURLYGPRHXPGBN-UHFFFAOYSA-N 0.000 description 1
- WRZDULJNVLZLHC-UHFFFAOYSA-N CC(C1)(OC)ON=C1c(c(Cl)c1)cc(-c2n[n](C)c(C(F)(F)F)c2Cl)c1F Chemical compound CC(C1)(OC)ON=C1c(c(Cl)c1)cc(-c2n[n](C)c(C(F)(F)F)c2Cl)c1F WRZDULJNVLZLHC-UHFFFAOYSA-N 0.000 description 1
- OAWCXSMQEWZCGJ-UHFFFAOYSA-N CC(OC(c(c(Cl)c1)cc(-c2n[n](C)c(C(F)(F)F)c2Cl)c1F)OC(C)=O)=O Chemical compound CC(OC(c(c(Cl)c1)cc(-c2n[n](C)c(C(F)(F)F)c2Cl)c1F)OC(C)=O)=O OAWCXSMQEWZCGJ-UHFFFAOYSA-N 0.000 description 1
- NOYPJFRXHUSDQL-UHFFFAOYSA-N CC(c(cc(C)c(Cl)c1)c1F)=O Chemical compound CC(c(cc(C)c(Cl)c1)c1F)=O NOYPJFRXHUSDQL-UHFFFAOYSA-N 0.000 description 1
- CAWFUWOEHHKPDC-SRZZPIQSSA-N C[n](c(C(F)(F)F)c1Cl)nc1-c(cc(/C(/Cl)=N\O)c(Cl)c1)c1F Chemical compound C[n](c(C(F)(F)F)c1Cl)nc1-c(cc(/C(/Cl)=N\O)c(Cl)c1)c1F CAWFUWOEHHKPDC-SRZZPIQSSA-N 0.000 description 1
- 235000011305 Capsella bursa pastoris Nutrition 0.000 description 1
- 240000008867 Capsella bursa-pastoris Species 0.000 description 1
- MKHDLSGGKWVJRI-UHFFFAOYSA-N Cc(c(Cl)c1)cc(C(CC(C(F)(F)F)=O)=O)c1F Chemical compound Cc(c(Cl)c1)cc(C(CC(C(F)(F)F)=O)=O)c1F MKHDLSGGKWVJRI-UHFFFAOYSA-N 0.000 description 1
- 244000037364 Cinnamomum aromaticum Species 0.000 description 1
- 235000014489 Cinnamomum aromaticum Nutrition 0.000 description 1
- 244000270200 Citrullus vulgaris Species 0.000 description 1
- 235000012840 Citrullus vulgaris Nutrition 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 241000234653 Cyperus Species 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 1
- 240000003176 Digitaria ciliaris Species 0.000 description 1
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 1
- 235000005476 Digitaria cruciata Nutrition 0.000 description 1
- 235000006830 Digitaria didactyla Nutrition 0.000 description 1
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 1
- QGLBZNZGBLRJGS-UHFFFAOYSA-N Dihydro-3-methyl-2(3H)-furanone Chemical compound CC1CCOC1=O QGLBZNZGBLRJGS-UHFFFAOYSA-N 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 235000003403 Limnocharis flava Nutrition 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 235000008406 SarachaNachtschatten Nutrition 0.000 description 1
- 235000004790 Solanum aculeatissimum Nutrition 0.000 description 1
- 235000008424 Solanum demissum Nutrition 0.000 description 1
- 235000018253 Solanum ferox Nutrition 0.000 description 1
- 235000000208 Solanum incanum Nutrition 0.000 description 1
- 235000013131 Solanum macrocarpon Nutrition 0.000 description 1
- 235000009869 Solanum phureja Nutrition 0.000 description 1
- 240000002307 Solanum ptychanthum Species 0.000 description 1
- 235000000341 Solanum ptychanthum Nutrition 0.000 description 1
- 235000017622 Solanum xanthocarpum Nutrition 0.000 description 1
- STSCVKRWJPWALQ-UHFFFAOYSA-N TRIFLUOROACETIC ACID ETHYL ESTER Chemical compound CCOC(=O)C(F)(F)F STSCVKRWJPWALQ-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 235000012735 amaranth Nutrition 0.000 description 1
- 239000004178 amaranth Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- PMMYEEVYMWASQN-QWWZWVQMSA-N cis-4-hydroxy-D-proline Chemical compound O[C@H]1C[NH2+][C@@H](C([O-])=O)C1 PMMYEEVYMWASQN-QWWZWVQMSA-N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 1
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 description 1
- 125000004671 dialkylaminothiocarbonyl group Chemical group 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- ZEFVHSWKYCYFFL-UHFFFAOYSA-N diethyl 2-methylidenebutanedioate Chemical compound CCOC(=O)CC(=C)C(=O)OCC ZEFVHSWKYCYFFL-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- ACQFOMVLRAEQCK-UHFFFAOYSA-N ethyl 2-hydroxy-3-methylbut-3-enoate Chemical compound CCOC(=O)C(O)C(C)=C ACQFOMVLRAEQCK-UHFFFAOYSA-N 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- NONOKGVFTBWRLD-UHFFFAOYSA-N isocyanatosulfanylimino(oxo)methane Chemical compound O=C=NSN=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 description 1
- 150000002547 isoxazolines Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GTRBXMICTQNNIN-UHFFFAOYSA-N methyl 2-(trifluoromethyl)prop-2-enoate Chemical compound COC(=O)C(=C)C(F)(F)F GTRBXMICTQNNIN-UHFFFAOYSA-N 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- QQZXAODFGRZKJT-UHFFFAOYSA-N n-tert-butyl-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NC(C)(C)C QQZXAODFGRZKJT-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 238000011176 pooling Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- 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
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- 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
-
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- 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
- C07D413/10—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 carbon chain containing aromatic rings
-
- 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
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
Definitions
- the invention belongs to the field of agricultural herbicides, and specifically relates to a phenylisoxazoline compound and its use.
- CN1939127 discloses CK-1 (Compound No. 9) and CK-2 (Compound No. 12) and has certain herbicidal activity.
- CN105753853 discloses isoxazoline compounds CK-3 (Compound No. 5) and CK-4 (Compound No. 7) with herbicidal activity.
- the present invention provides a phenylisoxazoline compound and its use.
- the present invention provides a phenylisoxazoline compound, as shown in the general formula (I):
- R 1 and R 2 are each selected from hydrogen, halogen or C 1 -C 6 alkyl
- R 3 is selected from hydrogen, cyano, C 1 -C 6 alkyl, phenyl, or phenyl substituted with 1-4 independently selected from the group consisting of halogen, CN, NO 2 , C 1 -C 6 alkyl , C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio or C 1 -C 6 alkylsulfonyl;
- R 4 is selected from hydrogen, cyano, C 1 -C 6 alkyl, CO 2 R 7 or CH 2 OR 8 ;
- R 5 is selected from hydrogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 alkyl CO 2 R 7 , CO 2 R 8 , CH 2 SiC [three (C 1 -C 6 alkyl)], unsubstituted or phenyl substituted with 1-4 independently selected from the following groups, the following groups are: halogen, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio Or C 1 -C 6 alkylsulfonyl;
- R 6 is selected from hydrogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkyl CO 2 R 7 , CO 2 R 7 , CH 2 OR 8 , CH 2 NR 9 R 10 , CONR 9 R 10 , unsubstituted or phenyl substituted with 1-4 independently selected from the following groups, the following groups are : Halogen, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxy Carbonyl, C 1 -C 6 alkylthio or C 1 -C 6 alkylsulfonyl;
- R 5 and R 6 may be connected with adjacent C to form a three-membered ring, a four-membered ring, a five-membered ring or a six-membered ring;
- R 3 and R 5 may be connected with adjacent C to form a five-membered ring or a six-membered ring;
- R 7 is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1- C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy C 2 -C 4 alkyl, C 2 -C 6 alkenyl carbonyloxy C 2 -C 4 alkyl, two (C 1- C 6 alkyl) amino C 2 -C 4 alkyl, (C 1 -C 6 alkyl) amino C 2 -C 4 alkyl, unsubstituted or substituted with 1-4 independently selected from the following groups Phenyl, benzyl, furimethylene, thiazolymethylene, tetrahydrofurimethylene or pyridine methylene, the following groups are: halogen, CN, NO 2 , C 1 -C 6 alkyl
- R 8 is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 3 -C 6 halocycloalkylcarbonyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 alkylamino Sulfonyl, di(C 1 -C 6 )alkylaminosulfonyl, C 1 -C 6 alkylaminocarbonyl, di(C 1 -C 6 )alkylaminocarbonyl, di(C 1 -C 6 )alkylaminocarbonyl, di(C 1 -C 6 )alkyl Aminothiocarbonyl
- R 9 and R 10 are respectively selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, SO 2 NH (C 1- C 6 alkyl) or SO 2 N (C 1 -C 6 alkyl) (C 1 -C 6 alkyl);
- Q is selected from any of the following Q1-Q13;
- R 11 is selected from C 1 -C 6 alkyl or C 1 -C 6 haloalkyl
- R 12 is selected from C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy;
- R 13 is selected from hydrogen, halogen, CN, NO 2 or C 1 -C 6 alkyl;
- R 14 is selected from C 1 -C 6 alkyl or C 1 -C 6 haloalkyl
- R 15 is selected from C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl or C 1 -C 6 haloalkyl;
- the preferred compound of the present invention is: in the general formula (I)
- R 1 and R 2 are each selected from hydrogen, halogen or C 1 -C 4 alkyl
- R 3 is selected from hydrogen, cyano, C 1 -C 4 alkyl, phenyl, or phenyl substituted with 1-4 independently selected from the following groups: halogen, CN, NO 2 , C 1 -C 4 alkyl , C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkoxycarbonyl;
- R 4 is selected from hydrogen, cyano, C 1 -C 4 alkyl, CO 2 R 7 or CH 2 OR 8 ;
- R 5 is selected from hydrogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 alkyl CO 2 R 7 , CO 2 R 7 , CH 2 Si [tris (C 1 -C 6 alkyl)], unsubstituted or phenyl substituted with 1-4 independently selected from the following groups: halogen, CN, NO 2 , C 1 -C 4 alkyl , C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
- R 6 is selected from hydrogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkyl CO 2 R 7 , CO 2 R 7 , CH 2 OR 8 , CH 2 NR 9 R 10 , CONR 9 R 10 , unsubstituted or phenyl substituted with 1-4 independently selected from the following groups: halogen, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
- R 5 and R 6 may be connected with adjacent C to form a four-membered ring or a five-membered ring;
- R 3 and R 5 may be connected with adjacent C to form a five-membered ring or a six-membered ring;
- R 7 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1- C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy C 2 -C 4 alkyl, C 2 -C 6 alkenyl carbonyloxy C 2 -C 4 alkyl, two (C 1- C 6 alkyl) amino C 2 -C 4 alkyl, (C 1 -C 6 alkyl) amino C 2 -C 4 alkyl, unsubstituted or substituted with 1-4 independently selected from the following groups Phenyl, benzyl, furylidene, thiazolyl, tetrahydrofurylidene or pyridinemethylene, the following groups are: halogen, CN, NO 2 , C 1 -C 4 al
- R 8 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 3 -C 6 halocycloalkylcarbonyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylamino Sulfonyl, di(C 1 -C 4 )alkylaminosulfonyl, C 1 -C 4 alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkyl Aminothiocarbonyl
- R 9 and R 10 are respectively selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxycarbonyl C 1 -C 4 alkyl, SO 2 NH (C 1- C 4 alkyl) or SO 2 N (C 1 -C 4 alkyl) (C 1 -C 4 alkyl);
- Q is selected from any of the following Q1-Q13;
- R 11 is selected from C 1 -C 4 alkyl or C 1 -C 4 haloalkyl
- R 12 is selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
- R 13 is selected from hydrogen, halogen, CN, NO 2 or C 1 -C 4 alkyl;
- R 14 is selected from C 1 -C 4 alkyl or C 1 -C 4 haloalkyl
- R 15 is selected from C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl or C 1 -C 4 haloalkyl;
- a further preferred compound of the present invention is: in the general formula (I)
- R 1 and R 2 are respectively selected from hydrogen, halogen, methyl, ethyl, propyl or isopropyl;
- R 3 is selected from hydrogen, cyano, C 1 -C 4 alkyl, phenyl or phenyl substituted with 1-2 independently selected from the following groups: fluorine, chlorine, bromine, CN, NO 2 , methyl, Ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, tert-butoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy Radical or difluoroethoxy;
- R 4 is selected from hydrogen, cyano or C 1 -C 4 alkyl
- R 5 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, trifluoroethyl, CH 2 CO 2 R 7 , CO 2 R 7 , CH 2 SiC(CH 3 ) 3 , unsubstituted or phenyl substituted with 1-2 independently selected from the following groups, the following groups are: fluorine, chlorine, bromine , CN, NO 2 , methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, tert-butoxy, difluoromethoxy, three Fluoromethoxy, trifluoroethoxy or difluoroethoxy;
- R 6 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butyl Oxy, cyclopropyl, cyclopentyl, cyclohexyl, CH 2 CO 2 R 7 , CH 2 CH 2 CO 2 R 7 , CO 2 R 7 , CH 2 OR 8 , CH 2 NR 9 R 10 , CONR 9 R 10.
- Unsubstituted or substituted by 1-2 groups independently selected from the following groups, the following groups are: fluorine, chlorine, bromine, CN, NO 2 , methyl, ethyl, isopropyl, tert-butyl , Trifluoromethyl, difluoromethyl, methoxy, ethoxy, tert-butoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy or difluoroethoxy;
- R 5 and R 6 may be connected with adjacent C to form a four-membered ring or a five-membered ring;
- R 3 and R 5 may be connected with adjacent C to form a five-membered ring or a six-membered ring;
- R 7 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1- C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy C 2 -C 4 alkyl, C 2 -C 6 alkenyl carbonyloxy C 2 -C 4 alkyl, two (C 1- C 6 alkyl) amino C 2 -C 4 alkyl, (C 1 -C 6 alkyl) amino C 2 -C 4 alkyl, unsubstituted or substituted with 1-4 independently selected from the following groups Phenyl, benzyl, furanmethylene or tetrahydrofuranmethylene: fluorine, chlorine, bromine, CN, NO 2 , methyl, ethyl, isopropyl, tert-buty
- R 8 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 3 -C 6 halocycloalkylcarbonyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 3 alkylamino Sulfonyl, di(C 1 -C 3 )alkylaminosulfonyl, C 1 -C 3 alkylaminocarbonyl, di(C 1 -C 3 )alkylaminocarbonyl, di(C 1 -C 3 )alkylaminocarbonyl, di(C 1 -C 3 )alkyl Aminothiocarbonyl
- R 9 and R 10 are respectively selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxycarbonyl C 1 -C 4 alkyl, SO 2 NH (C 1- C 4 alkyl) or SO 2 N (C 1 -C 4 alkyl) (C 1 -C 4 alkyl);
- Q is selected from any of the following Q1-Q13;
- R 11 is selected from C 1 -C 4 alkyl or C 1 -C 2 haloalkyl
- R 12 is selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
- R 13 is selected from hydrogen, halogen or C 1 -C 4 alkyl
- R 14 is selected from C 1 -C 4 alkyl or C 1 -C 2 haloalkyl
- R 15 is selected from C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl or C 1 -C 2 haloalkyl;
- the more preferred compound of the present invention is: in general formula (I)
- R 1 and R 2 are respectively selected from hydrogen, fluorine, chlorine, bromine or methyl;
- R 3 is selected from hydrogen, cyano, C 1 -C 4 alkyl, phenyl or phenyl substituted with 1-2 groups independently selected from the following: fluorine, chlorine, bromine or methyl;
- R 4 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl or tert-butyl;
- R 5 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, trifluoroethyl, CH 2 CO 2 R 7 , CO 2 R 7 , CH 2 SiC(CH 3 ) 3 , unsubstituted or phenyl substituted with 1-2 independently selected from the following groups: fluorine, chlorine, bromine, CN, NO 2 , Methyl, isopropyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy;
- R 6 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butyl Oxy, cyclopropyl, cyclopentyl, cyclohexyl, CH 2 CO 2 R 7 , CH 2 CH 2 CO 2 R 7 , CO 2 R 7 , CH 2 OR 8 , CONR 9 R 10 , unsubstituted or 1 -2 independently substituted phenyl groups selected from the following groups: fluorine, chlorine, bromine, CN, NO 2 , methyl, isopropyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethyl Oxy;
- R 5 and R 6 can be connected with adjacent C to form a tetrahydrofuranone ring
- R 3 and R 5 can be connected with adjacent C to form cyclopentane or cyclohexane
- R 7 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, allyl, propargyl, C 1 -C 3 alkoxy C 1- C 3 alkyl, C 1 -C 4 alkylcarbonyloxy C 2 -C 3 alkyl, C 2 -C 4 alkenyl carbonyloxy C 2 -C 3 alkyl, di(C 1 -C 3 alkyl)amino C 2 -C 3 alkyl, (C 1 -C 3 alkyl) amino C 2 -C 3 alkyl, unsubstituted or substituted by 1-4 independently selected from the following groups of phenyl, benzyl, furanolide Methyl or tetrahydrofuran methylene: fluorine, chlorine, bromine, CN, NO 2 , methyl, ethyl, isopropyl or tert-butyl;
- R 8 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, di(C 1 -C 3 )alkylaminosulfonyl, C 1 -C 3 alkane Alkylaminocarbonyl, di(C 1 -C 3 )alkylaminocarbonyl, C 1 -C 2 alkylthio C 2 -C 4 alkylcarbonyl, unsubstituted or benzene with 1-3 independently selected from the following groups Carbonyl, phenylacetyl, phenylpropionyl, phenoxy C 1 -C
- R 9 and R 10 are respectively selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 3 alkoxycarbonyl C 1 -C 2 alkyl, SO 2 NH (C 1- C 4 alkyl) or SO 2 N (C 1 -C 2 alkyl) (C 1 -C 4 alkyl);
- Q is selected from any of the following Q1-Q13;
- R 11 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, difluoromethyl, trifluoroethyl or difluoroethyl;
- R 12 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, isopropoxy, tert Butoxy, trifluoromethoxy, difluoromethoxy, trifluoroethoxy or difluoroethoxy;
- R 13 is selected from hydrogen, fluorine, chlorine, bromine, methyl or ethyl
- R 14 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, difluoromethyl, trifluoroethyl or difluoroethyl;
- R 15 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, cyclopropyl, difluoromethyl, trifluoromethyl, trifluoroethyl or difluoroethyl;
- a further preferred compound of the present invention is: in the general formula (I)
- R 1 and R 2 are respectively selected from hydrogen, fluorine, chlorine or bromine;
- R 3 is selected from hydrogen or C 1 -C 4 alkyl
- R 4 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl or tert-butyl;
- R 5 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, trifluoromethyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5.
- R 6 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butyl Oxy, cyclopropyl, cyclopentyl, cyclohexyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5 , CH 2 CH 2 CO 2 CH 3 , CH 2 CH 2 CO 2 C 2 H 5 , CO 2 R 7 , CH 2 OR 8 , CONR 9 R 10 , unsubstituted or phenyl substituted with 1-2 independently selected from the following groups: fluorine, chlorine or bromine;
- R 5 and R 6 can be connected with adjacent C to form a tetrahydrofuranone ring
- R 3 and R 5 can be connected with adjacent C to form cyclopentane or cyclohexane
- R 7 is selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, trifluoroethyl, difluoroethyl, 1-chloroethyl, 1- Fluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl, allyl, propargyl, methoxyethyl, ethoxyethyl, acetoxyethyl, acryloxyethyl, methyl Acryloyloxy, dimethylaminoethyl, diethylaminoethyl, diisopropylaminoethyl, methylaminoethyl, ethylaminoethyl, isopropylaminoethyl, tert-butylaminoethyl, methylene tetrahydrofuran Group
- R 8 is selected from hydrogen, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 1 -C 4 alkane Alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, di(C 1 -C 2 )alkylaminosulfonyl, C 1 -C 2 alkylaminocarbonyl, di(C 1 -C 3 )alkylaminocarbonyl , C 1 -C 2 alkylthio C 2 -C 4 alkylcarbonyl, unsubstituted or by 1-3 independently selected from the following groups phenylcarbonyl, phenylacetyl, phenylpropionyl, phenoxy C 1 -C 2 alkyl carbonyl or quinoline carbonyl: fluorine, chlorine, bro
- R 9 is selected from hydrogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl
- R 10 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 3 alkoxycarbonyl C 1 -C 2 alkyl, SO 2 NH (C 1 -C 4 alkyl) or SO 2 N (C 1 -C 2 alkyl) (C 1 -C 4 alkyl);
- Q is selected from the following Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8 or Q13;
- R 11 is selected from methyl, ethyl, isopropyl, tert-butyl, difluoromethyl, trifluoroethyl or difluoroethyl;
- R 12 is selected from methyl, trifluoromethyl, difluoromethyl, methoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, trifluoroethoxy or difluoroethoxy;
- R 13 is selected from hydrogen, fluorine, chlorine, bromine or methyl
- R 14 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl or tert-butyl;
- R 15 is selected from methyl, cyclopropyl or trifluoromethyl
- the further preferred compound of the present invention is: in the general formula (I)
- R 1 and R 2 are each selected from hydrogen, fluorine or chlorine
- R 3 is selected from hydrogen or C 1 -C 4 alkyl
- R 4 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl or tert-butyl;
- R 5 is selected from hydrogen, methyl, ethyl, trifluoromethyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5 , CO 2 CH 3 , CO 2 C 2 H 5 , CH 2 SiC (CH 3 ) 3.
- Unsubstituted or substituted phenyl groups independently selected from the following groups: fluorine, chlorine or bromine;
- R 6 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butyl Oxy, cyclopropyl, cyclopentyl, cyclohexyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5 , CH 2 CH 2 CO 2 CH 3 , CH 2 CH 2 CO 2 C 2 H 5 , CO 2 R 7 , CH 2 OR 8 , CONR 9 R 10 , unsubstituted or phenyl substituted with 1-2 independently selected from the following groups: fluorine, chlorine or bromine;
- R 5 and R 6 can be connected with adjacent C to form a tetrahydrofuranone ring
- R 3 and R 5 can be connected with adjacent C to form cyclopentane or cyclohexane
- R 7 is selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, trifluoroethyl, difluoroethyl, 1-chloroethyl, 1- Fluoroethyl, cyclopropyl, cyclohexyl, allyl, propargyl, methoxyethyl, ethoxyethyl, acetoxyethyl, acryloxyethyl, methacryloxy , Dimethylaminoethyl, diisopropylaminoethyl, methylaminoethyl, ethylaminoethyl, isopropylaminoethyl, tert-butylaminoethyl, tetrahydrofuranmethylene, unsubstituted or 1-2 Independently selected from the phenyl substituted by the
- R 8 is selected from hydrogen, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, cyclopropanoyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, two (C 1 -C 2 )alkylaminosulfonyl, di(C 1 -C 3 )alkylaminocarbonyl, C 1 -C 2 alkylthio, C 2 -C 4 alkylcarbonyl, phenylacetyl, phenylpropionyl , 2-Methyl-4-chlorophenoxyacetyl, 2,4-dichlorophenoxyacetyl,
- R 9 is selected from hydrogen, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, trifluoroethyl, difluoroethyl, 1-chloroethyl, 1-chloropropyl or 2-chloropropyl;
- R 10 is selected from hydrogen, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, methoxycarbonylmethylene, ethoxycarbonylmethylene, SO 2 NHCH 3 , SO 2 NHC 2 H 5 , SO 2 N(CH 3 ) 2 or SO 2 N(CH 3 )[CH(CH 3 ) 2 ];
- Q is selected from the following Q1, Q2, Q3, Q4, Q5, Q6, Q7 or Q8;
- R 11 is selected from methyl, ethyl, isopropyl, tert-butyl, difluoromethyl, trifluoroethyl or difluoroethyl;
- R 12 is selected from methyl, trifluoromethyl, difluoromethyl, methoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, trifluoroethoxy or difluoroethoxy;
- R 13 is selected from hydrogen, chlorine, bromine or methyl
- R 14 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl or tert-butyl;
- R 1 and R 2 are each selected from hydrogen, fluorine or chlorine
- R 3 is selected from hydrogen, methyl or ethyl
- R 4 is selected from hydrogen or methyl
- R 5 is selected from hydrogen, methyl, ethyl, trifluoromethyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5 , CO 2 CH 3 , CO 2 C 2 H 5 or CH 2 SiC (CH 3 ) 3 ;
- R 6 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, cyclopropyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5 , CH 2 CH 2 CO 2 CH 3 , CH 2 CH 2 CO 2 C 2 H 5 or CO 2 R 7 ;
- R 5 and R 6 can be connected with adjacent C to form a tetrahydrofuranone ring
- R 3 and R 5 can be connected with adjacent C to form cyclopentane or cyclohexane
- R 7 is selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, trifluoroethyl, difluoroethyl, 1-chloroethyl, 1- Fluoroethyl, cyclopropyl, cyclohexyl, allyl, propargyl, methoxyethyl, ethoxyethyl, acetoxyethyl, acryloxyethyl, methacryloxy , Dimethylaminoethyl, diisopropylaminoethyl, methylaminoethyl, ethylaminoethyl, isopropylaminoethyl, tert-butylaminoethyl, tetrahydrofuranmethylene, unsubstituted or 1-2 Independently selected from phenyl substituted by the following
- Q is selected from the following Q1, Q2, Q3, Q4, Q5, Q6, Q7 or Q8;
- R 11 is selected from methyl or difluoromethyl
- R 12 is selected from methyl, trifluoromethyl, difluoromethyl, isopropoxy, difluoromethoxy, trifluoroethoxy or difluoroethoxy;
- R 13 is selected from chlorine, bromine or methyl
- R 14 is selected from methyl, isopropyl, isobutyl or tert-butyl;
- Halogen refers to fluorine, chlorine, bromine or iodine.
- Alkyl straight or branched chain alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl or tert-butyl.
- Cycloalkyl A substituted or unsubstituted cyclic alkyl group, such as cyclopropyl, cyclopentyl or cyclohexyl. Substituents such as methyl, halogen and the like.
- Halogenated alkyl groups straight or branched chain alkyl groups.
- the hydrogen atoms on these alkyl groups can be partially or completely replaced by halogen atoms, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, dichloromethane Fluoromethyl, trifluoromethyl, etc.
- Alkoxy straight or branched chain alkyl, connected to the structure via an oxygen atom bond.
- Halogenated alkoxy groups straight-chain or branched-chain alkoxy groups. The hydrogen atoms on these alkoxy groups may be partially or completely replaced by halogen atoms.
- alkylthio straight or branched chain alkyl group, connected to the structure via a sulfur atom bond.
- Halogenated alkylthio linear or branched alkylthio. The hydrogen atoms on these alkyl groups can be partially or completely replaced by halogen atoms.
- Alkenyl straight or branched chain alkenes, such as vinyl, 1-propenyl, 2-propenyl and the different butenyl, pentenyl and hexenyl isomers. Alkenyl also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl.
- Alkylsulfonyl A straight or branched chain alkyl group is connected to the structure via a sulfonyl group (-SO 2 -), such as a methylsulfonyl group.
- Halogenated alkylsulfonyl linear or branched alkylsulfonyl, the hydrogen atoms on the alkyl group can be partially or completely replaced by halogen atoms.
- Alkylsulfinyl A straight or branched chain alkyl group is connected to the structure via a sulfonyl group (-SO-), such as a methylsulfinyl group.
- Halogenated alkylsulfonyl linear or branched alkylsulfinyl, the hydrogen atoms on the alkyl group can be partially or completely replaced by halogen atoms.
- Alkoxycarbonyl The alkoxy is connected to the structure via a carbonyl group, such as CH 3 OCO- or CH 3 CH 2 OCO-.
- Alkoxyalkyl alkyl-O-alkyl-, such as CH 3 OCH 2 -.
- Alkylcarbonyloxyalkoxycarbonyl alkyl-CO-O-alkyl- OCO-, such as CH 3 COOCH 2 OCO-, CH 3 COOCH 2 CH 2 OCO- or C 2 H 5 COOCH 2 CH 2 OCO-, etc.
- Alkylcarbonyl The alkyl group is connected to the structure via the carbonyl group, such as CH 3 CO- or CH 3 CH 2 CO-.
- Haloalkylcarbonyl The haloalkyl is connected to the structure via a carbonyl group, such as CF 3 CO- or CF 2 HCO-.
- Cycloalkylcarbonyl Cycloalkyl is connected to the structure via carbonyl, such as cyclopropanoyl or cyclohexylformyl.
- Halogenated cycloalkylcarbonyl group The halogenated cycloalkyl group is connected to the structure via a carbonyl group, such as 1-chlorocyclopropanoyl and the like.
- Alkylaminosulfonyl alkyl -NH-SO 2 -, such as CH 3 NHSO 2 -or C 2 H 5 NHSO 2 -and so on.
- Dialkylaminosulfonyl dialkyl-N-SO 2 -, such as (CH 3 ) 2 NSO 2 -or (C 2 H 5 ) 2 NSO 2 -, etc.
- Alkylaminocarbonyl alkyl-NH-CO-, such as CH 3 NHCO- or C 2 H 5 NHCO- etc.
- Dialkylaminocarbonyl dialkyl-N-CO-, such as (CH 3 ) 2 NCO- or (C 2 H 5 ) 2 NCO-, etc.
- Dialkylaminothiocarbonyl dialkyl-N-CS-, such as (CH 3 ) 2 NCS- or (C 2 H 5 ) 2 NCS-, etc.
- Alkylthioalkylcarbonyl alkyl-S-alkyl-CO, such as CH 3 SCH 2 CO or CH 3 SCH 2 CH 2 CO.
- Aryl polyvalent aromatic groups, such as phenyl and naphthyl. Heteroaryl is a five-membered ring or six-membered ring containing one or more N, O, S heteroatoms.
- SO 2 NH C 1 -C 4 alkyl: -SO 2 NHCH 3 or -SO 2 NHC 2 H 5 and the like.
- SO 2 N(C 1 -C 2 alkyl) C 1 -C 4 alkyl: -SO 2 N(CH 3 ) 2 or -SO 2 N(CH 3 )[CH(CH 3 ) 2 ], etc.
- Part of the compounds of the present invention can be illustrated by specific compounds listed in Table 1 to Table 35, but the present invention is not limited to these compounds.
- the compound of the present invention can be a compound represented by the general formula I-1, which can be obtained from the oxime-based compound III through chlorination ring closure by the method described in the literature, such as J.Agric.FoodChem. 2005,53,8639-8643, CN105753853, WO2006090234, etc.
- the oxime compound III can be obtained from the methyl intermediate VI through the oxidation of chromium trioxide by the method described in the literature, and the intermediate V is obtained by decarboxylation to obtain the aldehyde compound IV, which is then obtained through hydroxamidoximation, such as CN1402979, Chemical Reaction Engineering and Technology, 2002, 18(4), 373-376, Journal of Advanced Chemistry, 2003, 24(7), 1225-1230, etc.
- Methyl intermediate VI can be obtained from intermediate VII through bromination or chlorination of NBS, Br 2 , NCS or Cl 2 , or from intermediate XIV and hydrazine ring.
- Intermediate VII can be obtained by VIII and hydrazine ring or by re-etherification of X and hydrazine ring.
- Intermediate VIII can be obtained by reacting XI with R 2 CO 2 CH 3 , R 2 CO 2 C 2 H 5 , (R 2 CO) 2 O or R 2 COCl
- intermediate XIV can be obtained from XIII and R 2 CO 2 CH 3 , R 2 CO 2 C 2 H 5 , (R 2 CO) 2 O or R 2 COCl reaction, please refer to Bioorganic & Medicinal Chemistry, 2018, 26(12), 3406-3413, Tetrahedron Letters, 2016, 57(14) , 1555-1559, Handbook on Herbicides, 2014, 263-276, etc.
- X can be obtained by reacting XI with dimethyl carbonate or diethyl carbonate.
- the compound of the present invention can be a compound represented by the general formula I-2, which can be obtained by reacting intermediate XVI with acetic anhydride or acetyl chloride with the aid of the method described in the literature, and specifically Refer to the Journal of Heterocyclic Chemistry, 1987, 24(5), 1391-6, WO8501637 and WO2000034249; when Q is selected from Q6, the compound of the present invention may be a compound of general formula I-3, which can be obtained from intermediates by the method described in the literature XVI is obtained in two steps.
- the compound of the present invention can be a compound represented by the general formula I-4, which can be obtained from intermediate XVI in two steps by means of the method described in the literature.
- Literature can refer to EP860435, WO9817632, Organic Process Research & Development (2001), 5(6), 593-598 or EP448188.
- the compound of the present invention can effectively control barnyardgrass, setaria, alien sedge, cyperus, crabgrass, shepherd's purse, velvetleaf, zinnia, amaranth, purslane, cocklebur, nightshade, cassia , Wild watermelon seedlings, wild soybeans and other weeds, good results can be obtained at low doses. It has certain safety to wheat, corn and rice, and can be used as a herbicide in agriculture. Therefore, the present invention also includes the use of compounds of general formula (I) for controlling weeds.
- the compounds of the general formula (I) of the present invention are also suitable for drying and/or defoliating plants.
- 2-methoxypropene was replaced with 4-methyl-4-ethyl pentenoate, methyl methacrylate, and ethyl methacrylate.
- step 10 2-methoxypropene was replaced with isobutylene and 4- Ethyl methyl-4-pentenoate, methyl methacrylate, ethyl methacrylate, isopropyl methacrylate, ethylene glycol dimethacrylate, phenyl methacrylate, isobutyl methacrylate Ester, 2-(tert-butylamino) ethyl methacrylate, tetrahydrofurfuryl methacrylate, N-tert-butylmethacrylamide, 2-methylenylbutyrolactone, 2-(trimethylsilylmethyl) ) Ethyl acrylate, methyl trifluoromethacrylate, 1-cyclohexene-1-methyl methacrylate, methyl acrylate, ethyl acrylate, isobutyl acrylate
- the herbicidal activity test method of the compound of the invention is as follows:
- test design dose spray treatment (spray pressure 1.95kg/cm 2 , spray volume 500L/hm 2 , crawler speed 1.48km/h) on a crawler crop sprayer (designed and produced by British Engineer Research Ltd.).
- the test is set to be repeated 3 times. After the test materials are processed, they are placed in the operation hall. After the liquid is naturally dried in the shade, it is placed in the greenhouse for management according to conventional methods. Observation and recording of the weeds' response to the medicament is carried out. After treatment, the test medicament's control effect on weeds is regularly visually inspected.
- control effect classification standard 0 means invalid, 100% means complete kill or severe suppression of weeds.
- Tested for herbicidal activity Compounds 1-12, 1-16, 1-18, 1-19, 1-21, 1-23, 1-24, 1-29, 1-40, 1-42, 1-124, 1 -126, 1-194, 1-195, 1-301, 2-1, 2-12, 2-16, 2-18, 2-19, 2-23, 2-27, 2-32, 2-39 , 2-41, 2-42, 2-52, 2-124, 2-126, 2-160, 2-173, 2-194, 2-195, 2-214, 2-215, etc. at 600g ai/hm
- the herbicidal activity of pre-emergence and post-emergence treatments on Zinnia, Abutilon, Setaria and Barnyardgrass were all over 85%, showing higher activity.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Provided are a phenylisoxazoline compound and use thereof. The phenylisoxazoline compound is represented by general formula (I). The compound of general formula (I) has good herbicidal activity, and can effectively control barnyard grass, Setaria viridis, Cyperus difformis, Juncellus serotinus, Digitaria sanguinalis, Arthraxon hispidus, Abutilon theophrasti, Zinnia elegans, Amaranthus retroflexus, Portulaca oleracea, Xanthium strumarium, Solanum nigrum, Cassia tora, Hibiscus trionum, Glycine soja and other weeds; furthermore, the compound can obtain good weeding effect at low dosage, has certain safety to crops such as corn, wheat and rice, and can be used as a herbicide in agriculture.
Description
本发明属于农用除草剂领域，具体涉及一种苯基异恶唑啉类化合物及其用途。The invention belongs to the field of agricultural herbicides, and specifically relates to a phenylisoxazoline compound and its use.
苯基异恶唑啉类化合物作为除草剂研究有不少专利报道，如CN1939127中公开了CK-1(化合物编号9)和CK-2(化合物编号12)且具有一定的除草活性。There are many patent reports about phenylisoxazoline compounds as herbicides. For example, CN1939127 discloses CK-1 (Compound No. 9) and CK-2 (Compound No. 12) and has certain herbicidal activity.
CN105753853公开了具有除草活性的异噁唑啉类化合物CK-3(化合物编号5)和CK-4(化合物编号7)。CN105753853 discloses isoxazoline compounds CK-3 (Compound No. 5) and CK-4 (Compound No. 7) with herbicidal activity.
现有技术中，公开的化合物虽与本发明化合物有一定的相似之处，但本发明通式所示的化合物与现有技术是有显著区别的，且均具有更好的除草活性。In the prior art, although the disclosed compounds have certain similarities with the compounds of the present invention, the compounds represented by the general formula of the present invention are significantly different from the prior art, and both have better herbicidal activity.
发明内容Summary of the invention
为了研制新型除草剂以解决日益严重的除草剂抗性问题，本发明提供一种苯基异恶唑啉类化合物及其用途。In order to develop new herbicides to solve the increasingly serious problem of herbicide resistance, the present invention provides a phenylisoxazoline compound and its use.
为实现上述目的，本发明采用的技术方案如下：In order to achieve the above objectives, the technical solutions adopted by the present invention are as follows:
本发明提供一种苯基异恶唑啉类化合物，如通式(I)所示：The present invention provides a phenylisoxazoline compound, as shown in the general formula (I):
式中：Where:
R
1、R
2分别选自氢、卤素或C
1-C
6烷基；
R 1 and R 2 are each selected from hydrogen, halogen or C 1 -C 6 alkyl;
R
3选自氢、氰基、C
1-C
6烷基、苯基或被1-4个独立选自以下基团取代的苯基：卤素、CN、NO
2、C
1-C
6烷基、C
1-C
6卤代烷基、C
1-C
6烷氧基、C
1-C
6卤代烷氧基、C
1-C
6烷氧基羰基、C
1-C
6烷硫基或C
1-C
6烷基磺酰基；
R 3 is selected from hydrogen, cyano, C 1 -C 6 alkyl, phenyl, or phenyl substituted with 1-4 independently selected from the group consisting of halogen, CN, NO 2 , C 1 -C 6 alkyl , C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio or C 1 -C 6 alkylsulfonyl;
R
4选自氢、氰基、C
1-C
6烷基、CO
2R
7或CH
2OR
8；
R 4 is selected from hydrogen, cyano, C 1 -C 6 alkyl, CO 2 R 7 or CH 2 OR 8 ;
R
5选自氢、氰基、C
1-C
6烷基、C
1-C
6烷氧基、C
1-C
6卤代烷基、C
1-C
6烷基CO
2R
7、CO
2R
8、CH
2SiC[三(C
1-C
6烷基)]、未取代或被1-4个独立选自以下基团取代的苯基，以下基团为：卤素、CN、NO
2、C
1-C
6烷基、C
1-C
6卤代烷基、C
1-C
6烷氧基、C
1-C
6卤代烷氧基、C
1-C
6烷氧基羰基、C
1-C
6烷硫基或C
1-C
6烷基磺酰基；
R 5 is selected from hydrogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 alkyl CO 2 R 7 , CO 2 R 8 , CH 2 SiC [three (C 1 -C 6 alkyl)], unsubstituted or phenyl substituted with 1-4 independently selected from the following groups, the following groups are: halogen, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio Or C 1 -C 6 alkylsulfonyl;
R
6选自氢、氰基、C
1-C
6烷基、C
1-C
6烷氧基、C
1-C
6卤代烷基、C
3-C
6环烷基、C
1-C
6烷基CO
2R
7、CO
2R
7、CH
2OR
8、CH
2NR
9R
10、CONR
9R
10、未取代或被1-4个独立选自以下基团 取代的苯基,以下基团为：卤素、CN、NO
2、C
1-C
6烷基、C
1-C
6卤代烷基、C
1-C
6烷氧基、C
1-C
6卤代烷氧基、C
1-C
6烷氧基羰基、C
1-C
6烷硫基或C
1-C
6烷基磺酰基；
R 6 is selected from hydrogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkyl CO 2 R 7 , CO 2 R 7 , CH 2 OR 8 , CH 2 NR 9 R 10 , CONR 9 R 10 , unsubstituted or phenyl substituted with 1-4 independently selected from the following groups, the following groups are : Halogen, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxy Carbonyl, C 1 -C 6 alkylthio or C 1 -C 6 alkylsulfonyl;
R
5、R
6可与相邻的C连接形成三元环、四元环、五元环或者六元环；
R 5 and R 6 may be connected with adjacent C to form a three-membered ring, a four-membered ring, a five-membered ring or a six-membered ring;
R
3、R
5可与相邻的C连接形成五元环或者六元环；
R 3 and R 5 may be connected with adjacent C to form a five-membered ring or a six-membered ring;
R
7选自氢、C
1-C
6烷基、C
1-C
6卤代烷基、C
3-C
6环烷基、C
3-C
6烯基、C
3-C
6炔基、C
1-C
6烷氧基C
1-C
6烷基、C
1-C
6烷羰基氧基C
2-C
4烷基、C
2-C
6烯羰基氧基C
2-C
4烷基、二(C
1-C
6烷基)氨基C
2-C
4烷基、(C
1-C
6烷基)氨基C
2-C
4烷基，未取代或者被1-4个独立选自以下基团取代的苯基、苄基、呋喃亚甲基、噻唑亚甲基、四氢呋喃亚甲基或吡啶亚甲基，以下基团为：卤素、CN、NO
2、C
1-C
6烷基、C
1-C
6卤代烷基、C
1-C
6烷氧基、C
1-C
6卤代烷氧基、C
1-C
6烷氧基羰基、C
1-C
6烷硫基或C
1-C
6烷基磺酰基；
R 7 is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1- C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy C 2 -C 4 alkyl, C 2 -C 6 alkenyl carbonyloxy C 2 -C 4 alkyl, two (C 1- C 6 alkyl) amino C 2 -C 4 alkyl, (C 1 -C 6 alkyl) amino C 2 -C 4 alkyl, unsubstituted or substituted with 1-4 independently selected from the following groups Phenyl, benzyl, furimethylene, thiazolymethylene, tetrahydrofurimethylene or pyridine methylene, the following groups are: halogen, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio or C 1 -C 6 alkylsulfonyl ；
R
8选自氢、C
1-C
6烷基、C
1-C
6卤代烷基、C
1-C
6烷氧基羰基、C
1-C
6烷基羰基、C
1-C
6卤代烷基羰基、C
3-C
6环烷基羰基、C
3-C
6卤代环烷基羰基、C
1-C
6烷基磺酰基、C
1-C
6卤代烷基磺酰基、C
1-C
6烷基氨基磺酰基、二(C
1-C
6)烷基氨基磺酰基、C
1-C
6烷基氨基羰基、二(C
1-C
6)烷基氨基羰基、二(C
1-C
6)烷基氨基硫代羰基、C
1-C
6烷硫基C
2-C
6烷基羰基，未取代或者被1-4个独立选自以下基团取代的苯基、苯基C
1-C
2烷基、苯基C
2-C
4烯基、苯基羰基、苯基C
1-C
2烷基羰基、苯氧基C
1-C
2烷基羰基、苯基C
2-C
4烯基羰基、杂芳基、杂芳基C
1-C
2烷基、杂芳基羰基，以下基团为：卤素、CN、NO
2、C
1-C
6烷基、C
1-C
6卤代烷基、C
1-C
6烷氧基、C
1-C
6卤代烷氧基、C
1-C
6烷氧基羰基、C
1-C
6烷硫基、C
1-C
6烷基磺酰基或被1-4个独立所述基团取代的苯氧基：所述基团为卤素、CN、NO
2、C
1-C
6烷基、C
1-C
6卤代烷基、C
1-C
6烷氧基或C
1-C
6卤代烷氧基；
R 8 is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 3 -C 6 halocycloalkylcarbonyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 alkylamino Sulfonyl, di(C 1 -C 6 )alkylaminosulfonyl, C 1 -C 6 alkylaminocarbonyl, di(C 1 -C 6 )alkylaminocarbonyl, di(C 1 -C 6 )alkyl Aminothiocarbonyl, C 1 -C 6 alkylthio, C 2 -C 6 alkylcarbonyl, unsubstituted or substituted by 1-4 independently selected from the following phenyl groups, phenyl C 1 -C 2 alkyl groups , Phenyl C 2 -C 4 alkenyl, phenyl carbonyl, phenyl C 1 -C 2 alkylcarbonyl, phenoxy C 1 -C 2 alkylcarbonyl, phenyl C 2 -C 4 alkenyl carbonyl, hetero Aryl, heteroaryl C 1 -C 2 alkyl, heteroaryl carbonyl, the following groups are: halogen, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1- C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl or independently by 1-4 Phenoxy substituted by the group: the group is halogen, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1- C 6 haloalkoxy;
R
9、R
10分别选自氢、C
1-C
6烷基、C
1-C
6卤代烷基、C
1-C
6烷氧基羰基C
1-C
6烷基、SO
2NH(C
1-C
6烷基)或SO
2N(C
1-C
6烷基)(C
1-C
6烷基)；
R 9 and R 10 are respectively selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, SO 2 NH (C 1- C 6 alkyl) or SO 2 N (C 1 -C 6 alkyl) (C 1 -C 6 alkyl);
Q选自如下Q1-Q13中任意一个；Q is selected from any of the following Q1-Q13;
R
11选自C
1-C
6烷基或C
1-C
6卤代烷基；
R 11 is selected from C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;
R
12选自C
1-C
6烷基、C
1-C
6卤代烷基、C
1-C
6烷氧基或C
1-C
6卤代烷氧基；
R 12 is selected from C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy;
R
13选自氢、卤素、CN、NO
2或C
1-C
6烷基；
R 13 is selected from hydrogen, halogen, CN, NO 2 or C 1 -C 6 alkyl;
R
14选自C
1-C
6烷基或C
1-C
6卤代烷基；
R 14 is selected from C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;
R
15选自C
1-C
6烷基、C
3-C
6环烷基或C
1-C
6卤代烷基；
R 15 is selected from C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl or C 1 -C 6 haloalkyl;
或，式(I)化合物的可农用盐或衍生物。Or, an agriculturally acceptable salt or derivative of the compound of formula (I).
本发明较为优选的化合物为：通式(I)中The preferred compound of the present invention is: in the general formula (I)
R
1、R
2分别选自氢、卤素或C
1-C
4烷基；
R 1 and R 2 are each selected from hydrogen, halogen or C 1 -C 4 alkyl;
R
3选自氢、氰基、C
1-C
4烷基、苯基或被1-4个独立选自以下基团取代的苯基：卤素、CN、NO
2、C
1-C
4烷基、C
1-C
4卤代烷基、C
1-C
4烷氧基、C
1-C
4卤代烷氧基或C
1-C
4烷氧基羰基；
R 3 is selected from hydrogen, cyano, C 1 -C 4 alkyl, phenyl, or phenyl substituted with 1-4 independently selected from the following groups: halogen, CN, NO 2 , C 1 -C 4 alkyl , C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkoxycarbonyl;
R
4选自氢、氰基、C
1-C
4烷基、CO
2R
7或CH
2OR
8；
R 4 is selected from hydrogen, cyano, C 1 -C 4 alkyl, CO 2 R 7 or CH 2 OR 8 ;
R
5选自氢、氰基、C
1-C
4烷基、C
1-C
4烷氧基、C
1-C
4卤代烷基、C
1-C
4烷基CO
2R
7、CO
2R
7、CH
2Si[三(C
1-C
6烷基)]、未取代或被1-4个独立选自以下基团取代的苯基：卤素、CN、NO
2、C
1-C
4烷基、C
1-C
4卤代烷基、C
1-C
4烷氧基或C
1-C
4卤代烷氧基；
R 5 is selected from hydrogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 alkyl CO 2 R 7 , CO 2 R 7 , CH 2 Si [tris (C 1 -C 6 alkyl)], unsubstituted or phenyl substituted with 1-4 independently selected from the following groups: halogen, CN, NO 2 , C 1 -C 4 alkyl , C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
R
6选自氢、氰基、C
1-C
6烷基、C
1-C
6烷氧基、C
1-C
6卤代烷基、C
3-C
6环烷基、C
1-C
6烷基CO
2R
7、CO
2R
7、CH
2OR
8、CH
2NR
9R
10、CONR
9R
10、未取代或被1-4个独立选自以下基团取代的苯基：卤素、CN、NO
2、C
1-C
4烷基、C
1-C
4卤代烷基、C
1-C
4烷氧基或C
1-C
4卤代烷氧基；
R 6 is selected from hydrogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkyl CO 2 R 7 , CO 2 R 7 , CH 2 OR 8 , CH 2 NR 9 R 10 , CONR 9 R 10 , unsubstituted or phenyl substituted with 1-4 independently selected from the following groups: halogen, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
R
5、R
6可与相邻的C连接形成四元环或五元环；
R 5 and R 6 may be connected with adjacent C to form a four-membered ring or a five-membered ring;
R
3、R
5可与相邻的C连接形成五元环或六元环；
R 3 and R 5 may be connected with adjacent C to form a five-membered ring or a six-membered ring;
R
7选自氢、C
1-C
4烷基、C
1-C
4卤代烷基、C
3-C
6环烷基、C
3-C
6烯基、C
3-C
6炔基、C
1-C
6烷氧基C
1-C
6烷基、C
1-C
6烷羰基氧基C
2-C
4烷基、C
2-C
6烯羰基氧基C
2-C
4烷基、二(C
1-C
6烷基)氨基C
2-C
4烷基、(C
1-C
6烷基)氨基C
2-C
4烷基，未取代或者被1-4个独立选自以下基团取代的苯基、苄基、呋喃亚甲基、噻唑亚甲基、四氢呋喃亚甲基或吡啶亚甲基，以下基团为：卤素、CN、NO
2、C
1-C
4烷基、C
1-C
8卤代烷基、C
1-C
4烷氧基、C
1-C
4卤代烷氧基或C
1-C
4烷氧基羰基；
R 7 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1- C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy C 2 -C 4 alkyl, C 2 -C 6 alkenyl carbonyloxy C 2 -C 4 alkyl, two (C 1- C 6 alkyl) amino C 2 -C 4 alkyl, (C 1 -C 6 alkyl) amino C 2 -C 4 alkyl, unsubstituted or substituted with 1-4 independently selected from the following groups Phenyl, benzyl, furylidene, thiazolyl, tetrahydrofurylidene or pyridinemethylene, the following groups are: halogen, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 8 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkoxycarbonyl group;
R
8选自氢、C
1-C
4烷基、C
1-C
4卤代烷基、C
1-C
4烷氧基羰基、C
1-C
4烷基羰基、C
1-C
6卤代烷基羰基、C
3-C
6环烷基羰基、C
3-C
6卤代环烷基羰基、C
1-C
4烷基磺酰基、C
1-C
4卤代烷基磺酰基、C
1-C
4烷基氨基磺酰基、二(C
1-C
4)烷基氨基磺酰基、C
1-C
4烷基氨基羰基、二(C
1-C
4)烷基氨基羰基、二(C
1-C
4)烷基氨基硫代羰基、C
1-C
4烷硫基C
2-C
4烷基羰基，未取代或者被1-4个独立选自以下基团取代的苯基、苯基C
1-C
2烷基、苯基C
2-C
4烯基、苯基羰基、苯基C
1-C
2烷基羰基、苯氧基C
1-C
2烷基羰基、苯基C
2-C
4烯基羰基、杂芳基、杂芳基C
1-C
2烷基、杂芳基羰基，以下基团为：卤素、CN、NO
2、C
1-C
4烷基、C
1-C
4卤代烷基、C
1-C
4烷氧基、C
1-C
4卤代烷氧基、C
1-C
4烷氧基羰基、C
1-C
4烷硫基、C
1-C
4烷基磺酰基或被1-4个独立的所述基团取代的苯氧基：所述基团为卤素、CN、NO
2、C
1-C
4烷基、C
1-C
4卤代烷基、C
1-C
4烷氧基或C
1-C
4卤代烷氧基；
R 8 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 3 -C 6 halocycloalkylcarbonyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylamino Sulfonyl, di(C 1 -C 4 )alkylaminosulfonyl, C 1 -C 4 alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkyl Aminothiocarbonyl, C 1 -C 4 alkylthio, C 2 -C 4 alkylcarbonyl, unsubstituted or substituted by 1-4 independently selected from the following phenyl groups, phenyl C 1 -C 2 alkyl groups , Phenyl C 2 -C 4 alkenyl, phenyl carbonyl, phenyl C 1 -C 2 alkylcarbonyl, phenoxy C 1 -C 2 alkylcarbonyl, phenyl C 2 -C 4 alkenyl carbonyl, hetero Aryl, heteroaryl C 1 -C 2 alkyl, heteroaryl carbonyl, the following groups are: halogen, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1- C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfonyl or independently by 1-4 The group substituted phenoxy group: the group is halogen, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
R
9、R
10分别选自氢、C
1-C
4烷基、C
1-C
4卤代烷基、C
1-C
4烷氧基羰基C
1-C
4烷基、SO
2NH(C
1-C
4烷基)或SO
2N(C
1-C
4烷基)(C
1-C
4烷基)；
R 9 and R 10 are respectively selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxycarbonyl C 1 -C 4 alkyl, SO 2 NH (C 1- C 4 alkyl) or SO 2 N (C 1 -C 4 alkyl) (C 1 -C 4 alkyl);
Q选自如下Q1-Q13中任意一个；Q is selected from any of the following Q1-Q13;
R
11选自C
1-C
4烷基或C
1-C
4卤代烷基；
R 11 is selected from C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
R
12选自C
1-C
4烷基、C
1-C
4卤代烷基、C
1-C
4烷氧基或C
1-C
4卤代烷氧基；
R 12 is selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
R
13选自氢、卤素、CN、NO
2或C
1-C
4烷基；
R 13 is selected from hydrogen, halogen, CN, NO 2 or C 1 -C 4 alkyl;
R
14选自C
1-C
4烷基或C
1-C
4卤代烷基；
R 14 is selected from C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
R
15选自C
1-C
4烷基、C
3-C
6环烷基或C
1-C
4卤代烷基；
R 15 is selected from C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl or C 1 -C 4 haloalkyl;
或，式(I)化合物的可农用盐或衍生物。Or, an agriculturally acceptable salt or derivative of the compound of formula (I).
本发明进一步优选的化合物为：通式(I)中A further preferred compound of the present invention is: in the general formula (I)
R
1、R
2分别选自氢、卤素、甲基、乙基、丙基或异丙基；
R 1 and R 2 are respectively selected from hydrogen, halogen, methyl, ethyl, propyl or isopropyl;
R
3选自氢、氰基、C
1-C
4烷基、苯基或被1-2个独立选自以下基团取代的苯基：氟、氯、溴、CN、NO
2、甲基、乙基、异丙基、叔丁基、三氟甲基、二氟甲基、甲氧基、乙氧基、叔丁氧基、二氟甲氧基、三氟甲氧基、三氟乙氧基或二氟乙氧基；
R 3 is selected from hydrogen, cyano, C 1 -C 4 alkyl, phenyl or phenyl substituted with 1-2 independently selected from the following groups: fluorine, chlorine, bromine, CN, NO 2 , methyl, Ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, tert-butoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy Radical or difluoroethoxy;
R
4选自氢、氰基或C
1-C
4烷基；
R 4 is selected from hydrogen, cyano or C 1 -C 4 alkyl;
R
5选自氢、氰基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、三氟甲基、 二氟甲基、三氟乙基、CH
2CO
2R
7、CO
2R
7、CH
2SiC(CH
3)
3、未取代或被1-2个独立选自以下基团取代的苯基，以下基团为：氟、氯、溴、CN、NO
2、甲基、乙基、异丙基、叔丁基、三氟甲基、二氟甲基、甲氧基、乙氧基、叔丁氧基、二氟甲氧基、三氟甲氧基、三氟乙氧基或二氟乙氧基；
R 5 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, trifluoroethyl, CH 2 CO 2 R 7 , CO 2 R 7 , CH 2 SiC(CH 3 ) 3 , unsubstituted or phenyl substituted with 1-2 independently selected from the following groups, the following groups are: fluorine, chlorine, bromine , CN, NO 2 , methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, tert-butoxy, difluoromethoxy, three Fluoromethoxy, trifluoroethoxy or difluoroethoxy;
R
6选自氢、氰基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、甲氧基、乙氧基、异丙氧基、叔丁氧基、环丙基、环戊基、环己基、CH
2CO
2R
7、CH
2CH
2CO
2R
7、CO
2R
7、CH
2OR
8、CH
2NR
9R
10、CONR
9R
10、未取代或被1-2个独立选自以下基团取代的苯基，以下基团为：氟、氯、溴、CN、NO
2、甲基、乙基、异丙基、叔丁基、三氟甲基、二氟甲基、甲氧基、乙氧基、叔丁氧基、二氟甲氧基、三氟甲氧基、三氟乙氧基或二氟乙氧基；
R 6 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butyl Oxy, cyclopropyl, cyclopentyl, cyclohexyl, CH 2 CO 2 R 7 , CH 2 CH 2 CO 2 R 7 , CO 2 R 7 , CH 2 OR 8 , CH 2 NR 9 R 10 , CONR 9 R 10. Unsubstituted or substituted by 1-2 groups independently selected from the following groups, the following groups are: fluorine, chlorine, bromine, CN, NO 2 , methyl, ethyl, isopropyl, tert-butyl , Trifluoromethyl, difluoromethyl, methoxy, ethoxy, tert-butoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy or difluoroethoxy;
R
5、R
6可与相邻的C连接形成四元环或五元环；
R 5 and R 6 may be connected with adjacent C to form a four-membered ring or a five-membered ring;
R
3、R
5可与相邻的C连接形成五元环或六元环；
R 3 and R 5 may be connected with adjacent C to form a five-membered ring or a six-membered ring;
R
7选自氢、C
1-C
4烷基、C
1-C
4卤代烷基、C
3-C
6环烷基、C
3-C
6烯基、C
3-C
6炔基、C
1-C
6烷氧基C
1-C
6烷基、C
1-C
6烷羰基氧基C
2-C
4烷基、C
2-C
6烯羰基氧基C
2-C
4烷基、二(C
1-C
6烷基)氨基C
2-C
4烷基、(C
1-C
6烷基)氨基C
2-C
4烷基，未取代或者被1-4个独立选自以下基团取代的苯基、苄基、呋喃亚甲基或四氢呋喃亚甲基：氟、氯、溴、CN、NO
2、甲基、乙基、异丙基、叔丁基、三氟甲基、甲氧基、乙氧基、叔丁氧基、二氟甲氧基、三氟甲氧基、三氟乙氧基或二氟乙氧基；
R 7 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1- C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy C 2 -C 4 alkyl, C 2 -C 6 alkenyl carbonyloxy C 2 -C 4 alkyl, two (C 1- C 6 alkyl) amino C 2 -C 4 alkyl, (C 1 -C 6 alkyl) amino C 2 -C 4 alkyl, unsubstituted or substituted with 1-4 independently selected from the following groups Phenyl, benzyl, furanmethylene or tetrahydrofuranmethylene: fluorine, chlorine, bromine, CN, NO 2 , methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, methoxy, Ethoxy, tert-butoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy or difluoroethoxy;
R
8选自氢、C
1-C
4烷基、C
1-C
4卤代烷基、C
1-C
4烷氧基羰基、C
1-C
4烷基羰基、C
1-C
4卤代烷基羰基、C
3-C
6环烷基羰基、C
3-C
6卤代环烷基羰基、C
1-C
4烷基磺酰基、C
1-C
4卤代烷基磺酰基、C
1-C
3烷基氨基磺酰基、二(C
1-C
3)烷基氨基磺酰基、C
1-C
3烷基氨基羰基、二(C
1-C
3)烷基氨基羰基、二(C
1-C
3)烷基氨基硫代羰基、C
1-C
2烷硫基C
2-C
4烷基羰基，未取代或者被1-4个独立选自以下基团取代的苯基C
1-C
2烷基、苯基羰基、苯基C
1-C
2烷基羰基、苯基C
2-C
4烯基羰基、苯氧基C
1-C
2烷基羰基、噻吩羰基、吡唑羰基、喹啉羰基，以下基团为：卤素、CN、NO
2、C
1-C
4烷基、C
1-C
4卤代烷基、C
1-C
4烷氧基、C
1-C
4卤代烷氧基、C
1-C
4烷氧基羰基、C
1-C
4烷硫基、C
1-C
4烷基磺酰基或被1-4个独立所述基团取代的苯氧基：所述基团为卤素、CN、NO
2、C
1-C
4烷基、C
1-C
4卤代烷基、C
1-C
4烷氧基或C
1-C
4卤代烷氧基；
R 8 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 3 -C 6 halocycloalkylcarbonyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 3 alkylamino Sulfonyl, di(C 1 -C 3 )alkylaminosulfonyl, C 1 -C 3 alkylaminocarbonyl, di(C 1 -C 3 )alkylaminocarbonyl, di(C 1 -C 3 )alkyl Aminothiocarbonyl, C 1 -C 2 alkylthio C 2 -C 4 alkylcarbonyl, unsubstituted or phenyl substituted with 1-4 independently selected from the following groups: C 1 -C 2 alkyl, phenyl Carbonyl, phenyl C 1 -C 2 alkylcarbonyl, phenyl C 2 -C 4 alkenyl carbonyl, phenoxy C 1 -C 2 alkylcarbonyl, thiophene carbonyl, pyrazole carbonyl, quinoline carbonyl, the following groups It is: halogen, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy Carbonyl group, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfonyl or phenoxy substituted by 1-4 independent groups: the groups are halogen, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
R
9、R
10分别选自氢、C
1-C
4烷基、C
1-C
4卤代烷基、C
1-C
4烷氧基羰基C
1-C
4烷基、SO
2NH(C
1-C
4烷基)或SO
2N(C
1-C
4烷基)(C
1-C
4烷基)；
R 9 and R 10 are respectively selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxycarbonyl C 1 -C 4 alkyl, SO 2 NH (C 1- C 4 alkyl) or SO 2 N (C 1 -C 4 alkyl) (C 1 -C 4 alkyl);
Q选自如下Q1-Q13中任意一个；Q is selected from any of the following Q1-Q13;
R
11选自C
1-C
4烷基或C
1-C
2卤代烷基；
R 11 is selected from C 1 -C 4 alkyl or C 1 -C 2 haloalkyl;
R
12选自C
1-C
4烷基、C
1-C
4卤代烷基、C
1-C
4烷氧基或C
1-C
4卤代烷氧基；
R 12 is selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
R
13选自氢、卤素或C
1-C
4烷基；
R 13 is selected from hydrogen, halogen or C 1 -C 4 alkyl;
R
14选自C
1-C
4烷基或C
1-C
2卤代烷基；
R 14 is selected from C 1 -C 4 alkyl or C 1 -C 2 haloalkyl;
R
15选自C
1-C
4烷基、C
3-C
6环烷基或C
1-C
2卤代烷基；
R 15 is selected from C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl or C 1 -C 2 haloalkyl;
或，式(I)化合物的可农用盐或衍生物。Or, an agriculturally acceptable salt or derivative of the compound of formula (I).
本发明更为优选的化合物为：通式(I)中The more preferred compound of the present invention is: in general formula (I)
R
1、R
2分别选自氢、氟、氯、溴或甲基；
R 1 and R 2 are respectively selected from hydrogen, fluorine, chlorine, bromine or methyl;
R
3选自氢、氰基、C
1-C
4烷基、苯基或被1-2个独立选自以下基团取代的苯基：氟、氯、溴或甲基；
R 3 is selected from hydrogen, cyano, C 1 -C 4 alkyl, phenyl or phenyl substituted with 1-2 groups independently selected from the following: fluorine, chlorine, bromine or methyl;
R
4选自氢、氰基、甲基、乙基、正丙基、异丙基或叔丁基；
R 4 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl or tert-butyl;
R
5选自氢、氰基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、三氟甲基、二氟甲基、三氟乙基、CH
2CO
2R
7、CO
2R
7、CH
2SiC(CH
3)
3、未取代或被1-2个独立选自以下基团取代的苯基：氟、氯、溴、CN、NO
2、甲基、异丙基、三氟甲基、甲氧基、二氟甲氧基或三氟甲氧基；
R 5 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, trifluoroethyl, CH 2 CO 2 R 7 , CO 2 R 7 , CH 2 SiC(CH 3 ) 3 , unsubstituted or phenyl substituted with 1-2 independently selected from the following groups: fluorine, chlorine, bromine, CN, NO 2 , Methyl, isopropyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy;
R
6选自氢、氰基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、甲氧基、 乙氧基、异丙氧基、叔丁氧基、环丙基、环戊基、环己基、CH
2CO
2R
7、CH
2CH
2CO
2R
7、CO
2R
7、CH
2OR
8、CONR
9R
10、未取代或被1-2个独立选自以下基团取代的苯基：氟、氯、溴、CN、NO
2、甲基、异丙基、三氟甲基、甲氧基、二氟甲氧基或三氟甲氧基；
R 6 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butyl Oxy, cyclopropyl, cyclopentyl, cyclohexyl, CH 2 CO 2 R 7 , CH 2 CH 2 CO 2 R 7 , CO 2 R 7 , CH 2 OR 8 , CONR 9 R 10 , unsubstituted or 1 -2 independently substituted phenyl groups selected from the following groups: fluorine, chlorine, bromine, CN, NO 2 , methyl, isopropyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethyl Oxy;
R
5、R
6可与相邻的C连接形成四氢呋喃酮环；
R 5 and R 6 can be connected with adjacent C to form a tetrahydrofuranone ring;
R
3、R
5可与相邻的C连接形成环戊烷或环己烷；
R 3 and R 5 can be connected with adjacent C to form cyclopentane or cyclohexane;
R
7选自氢、C
1-C
4烷基、C
1-C
4卤代烷基、C
3-C
6环烷基、烯丙基、炔丙基、C
1-C
3烷氧基C
1-C
3烷基、C
1-C
4烷羰基氧基C
2-C
3烷基，C
2-C
4烯羰基氧基C
2-C
3烷基、二(C
1-C
3烷基)氨基C
2-C
3烷基、(C
1-C
3烷基)氨基C
2-C
3烷基、未取代或者被1-4个独立选自以下基团取代的苯基、苄基、呋喃亚甲基或四氢呋喃亚甲基：氟、氯、溴、CN、NO
2、甲基、乙基、异丙基或叔丁基；
R 7 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, allyl, propargyl, C 1 -C 3 alkoxy C 1- C 3 alkyl, C 1 -C 4 alkylcarbonyloxy C 2 -C 3 alkyl, C 2 -C 4 alkenyl carbonyloxy C 2 -C 3 alkyl, di(C 1 -C 3 alkyl)amino C 2 -C 3 alkyl, (C 1 -C 3 alkyl) amino C 2 -C 3 alkyl, unsubstituted or substituted by 1-4 independently selected from the following groups of phenyl, benzyl, furanolide Methyl or tetrahydrofuran methylene: fluorine, chlorine, bromine, CN, NO 2 , methyl, ethyl, isopropyl or tert-butyl;
R
8选自氢、C
1-C
4烷基、C
1-C
4卤代烷基、C
1-C
4烷氧基羰基、C
1-C
4烷基羰基、C
1-C
4卤代烷基羰基、C
3-C
6环烷基羰基、C
1-C
4烷基磺酰基、C
1-C
4卤代烷基磺酰基、二(C
1-C
3)烷基氨基磺酰基、C
1-C
3烷基氨基羰基、二(C
1-C
3)烷基氨基羰基、C
1-C
2烷硫基C
2-C
4烷基羰基，未取代或者被1-3个独立选自以下基团的苯基羰基、苯乙酰基、苯丙酰基、苯氧基C
1-C
2烷基羰基或喹啉羰基：氟、氯、溴、CN、NO
2、C
1-C
4烷基、C
1-C
4卤代烷基、C
1-C
4烷氧基、C
1-C
4卤代烷氧基、C
1-C
4烷硫基或C
1-C
4烷基磺酰基；
R 8 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, di(C 1 -C 3 )alkylaminosulfonyl, C 1 -C 3 alkane Alkylaminocarbonyl, di(C 1 -C 3 )alkylaminocarbonyl, C 1 -C 2 alkylthio C 2 -C 4 alkylcarbonyl, unsubstituted or benzene with 1-3 independently selected from the following groups Carbonyl, phenylacetyl, phenylpropionyl, phenoxy C 1 -C 2 alkyl carbonyl or quinoline carbonyl: fluorine, chlorine, bromine, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio or C 1 -C 4 alkylsulfonyl;
R
9、R
10分别选自氢、C
1-C
4烷基、C
1-C
4卤代烷基、C
1-C
3烷氧基羰基C
1-C
2烷基、SO
2NH(C
1-C
4烷基)或SO
2N(C
1-C
2烷基)(C
1-C
4烷基)；
R 9 and R 10 are respectively selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 3 alkoxycarbonyl C 1 -C 2 alkyl, SO 2 NH (C 1- C 4 alkyl) or SO 2 N (C 1 -C 2 alkyl) (C 1 -C 4 alkyl);
Q选自如下Q1-Q13中任意一个；Q is selected from any of the following Q1-Q13;
R
11选自甲基、乙基、正丙基、异丙基、异丁基、叔丁基、二氟甲基、三氟乙基或二氟乙基；
R 11 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, difluoromethyl, trifluoroethyl or difluoroethyl;
R
12选自甲基、乙基、正丙基、异丙基、异丁基、叔丁基、三氟甲基、二氟甲基、甲氧基、乙氧基、异丙氧基、叔丁氧基、三氟甲氧基、二氟甲氧基、三氟乙氧基或者二氟乙氧基；
R 12 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, isopropoxy, tert Butoxy, trifluoromethoxy, difluoromethoxy, trifluoroethoxy or difluoroethoxy;
R
13选自氢、氟、氯、溴、甲基或乙基；
R 13 is selected from hydrogen, fluorine, chlorine, bromine, methyl or ethyl;
R
14选自甲基、乙基、正丙基、异丙基、异丁基、叔丁基、二氟甲基、三氟乙基或二氟乙基；
R 14 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, difluoromethyl, trifluoroethyl or difluoroethyl;
R
15选自甲基、乙基、正丙基、异丙基、异丁基、叔丁基、环丙基、二氟甲基、三氟甲基、三氟乙基或二氟乙基；
R 15 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, cyclopropyl, difluoromethyl, trifluoromethyl, trifluoroethyl or difluoroethyl;
或，式(I)化合物的可农用盐或衍生物。Or, an agriculturally acceptable salt or derivative of the compound of formula (I).
本发明再进一步较为优选的化合物为：通式(I)中A further preferred compound of the present invention is: in the general formula (I)
R
1、R
2分别选自氢、氟、氯或溴；
R 1 and R 2 are respectively selected from hydrogen, fluorine, chlorine or bromine;
R
3选自氢或C
1-C
4烷基；
R 3 is selected from hydrogen or C 1 -C 4 alkyl;
R
4选自氢、甲基、乙基、正丙基、异丙基或叔丁基；
R 4 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl or tert-butyl;
R
5选自氢、氰基、甲基、乙基、正丙基、异丙基、异丁基、叔丁基、三氟甲基、CH
2CO
2CH
3、CH
2CO
2C
2H
5、CO
2CH
3、CO
2C
2H
5、CH
2SiC(CH
3)
3、未取代或被1-2个独立选自以下基团取代的苯基：氟、氯或溴；
R 5 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, trifluoromethyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5. CO 2 CH 3 , CO 2 C 2 H 5 , CH 2 SiC(CH 3 ) 3 , unsubstituted or phenyl substituted with 1-2 independently selected from the following groups: fluorine, chlorine or bromine;
R
6选自氢、氰基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、甲氧基、乙氧基、异丙氧基、叔丁氧基、环丙基、环戊基、环己基、CH
2CO
2CH
3、CH
2CO
2C
2H
5、CH
2CH
2CO
2CH
3、CH
2CH
2CO
2C
2H
5、CO
2R
7、CH
2OR
8、CONR
9R
10、未取代或被1-2个独立选自以下基团取代的苯基：氟、氯或溴；
R 6 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butyl Oxy, cyclopropyl, cyclopentyl, cyclohexyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5 , CH 2 CH 2 CO 2 CH 3 , CH 2 CH 2 CO 2 C 2 H 5 , CO 2 R 7 , CH 2 OR 8 , CONR 9 R 10 , unsubstituted or phenyl substituted with 1-2 independently selected from the following groups: fluorine, chlorine or bromine;
R
5、R
6可与相邻的C连接形成四氢呋喃酮环；
R 5 and R 6 can be connected with adjacent C to form a tetrahydrofuranone ring;
R
3、R
5可与相邻的C连接形成环戊烷或环己烷；
R 3 and R 5 can be connected with adjacent C to form cyclopentane or cyclohexane;
R
7选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、三氟乙基、二氟乙基、1-氯乙基、1-氟乙基、环丙基、环戊基、环己基、烯丙基、炔丙基、甲氧基乙基、乙氧基乙基、乙酰氧基乙基、丙烯酰氧基乙基、甲基丙烯酰氧基、二甲氨基乙基、二乙氨基乙 基、二异丙基氨基乙基、甲氨基乙基、乙氨基乙基、异丙氨基乙基、叔丁氨基乙基、四氢呋喃亚甲基、未取代或被1-2个独立选自以下基团取代的苯基：氟、氯或溴；
R 7 is selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, trifluoroethyl, difluoroethyl, 1-chloroethyl, 1- Fluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl, allyl, propargyl, methoxyethyl, ethoxyethyl, acetoxyethyl, acryloxyethyl, methyl Acryloyloxy, dimethylaminoethyl, diethylaminoethyl, diisopropylaminoethyl, methylaminoethyl, ethylaminoethyl, isopropylaminoethyl, tert-butylaminoethyl, methylene tetrahydrofuran Group, unsubstituted or phenyl substituted with 1-2 groups independently selected from the group consisting of fluorine, chlorine or bromine;
R
8选自氢、C
1-C
4烷氧基羰基、C
1-C
4烷基羰基、C
1-C
4卤代烷基羰基、C
3-C
6环烷基羰基、C
1-C
4烷基磺酰基、C
1-C
4卤代烷基磺酰基、二(C
1-C
2)烷基氨基磺酰基、C
1-C
2烷基氨基羰基、二(C
1-C
3)烷基氨基羰基、C
1-C
2烷硫基C
2-C
4烷基羰基，未取代或者被1-3个独立选自以下基团的苯基羰基、苯乙酰基、苯丙酰基、苯氧基C
1-C
2烷基羰基或喹啉羰基：氟、氯、溴、CN、NO
2、C
1-C
4烷基、C
1-C
4卤代烷基、C
1-C
4烷氧基、C
1-C
4卤代烷氧基、或C
1-C
4烷基磺酰基；
R 8 is selected from hydrogen, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 1 -C 4 alkane Alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, di(C 1 -C 2 )alkylaminosulfonyl, C 1 -C 2 alkylaminocarbonyl, di(C 1 -C 3 )alkylaminocarbonyl , C 1 -C 2 alkylthio C 2 -C 4 alkylcarbonyl, unsubstituted or by 1-3 independently selected from the following groups phenylcarbonyl, phenylacetyl, phenylpropionyl, phenoxy C 1 -C 2 alkyl carbonyl or quinoline carbonyl: fluorine, chlorine, bromine, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1- C 4 haloalkoxy, or C 1 -C 4 alkylsulfonyl;
R
9选自氢、C
1-C
4烷基或C
1-C
4卤代烷基；
R 9 is selected from hydrogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
R
10选自氢、C
1-C
4烷基、C
1-C
3烷氧基羰基C
1-C
2烷基、SO
2NH(C
1-C
4烷基)或SO
2N(C
1-C
2烷基)(C
1-C
4烷基)；
R 10 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 3 alkoxycarbonyl C 1 -C 2 alkyl, SO 2 NH (C 1 -C 4 alkyl) or SO 2 N (C 1 -C 2 alkyl) (C 1 -C 4 alkyl);
Q选自如下Q1、Q2、Q3、Q4、Q5、Q6、Q7、Q8或Q13；Q is selected from the following Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8 or Q13;
R
11选自甲基、乙基、异丙基、叔丁基、二氟甲基、三氟乙基或二氟乙基；
R 11 is selected from methyl, ethyl, isopropyl, tert-butyl, difluoromethyl, trifluoroethyl or difluoroethyl;
R
12选自甲基、三氟甲基、二氟甲基、甲氧基、异丙氧基、三氟甲氧基、二氟甲氧基、三氟乙氧基或者二氟乙氧基；
R 12 is selected from methyl, trifluoromethyl, difluoromethyl, methoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, trifluoroethoxy or difluoroethoxy;
R
13选自氢、氟、氯、溴或甲基；
R 13 is selected from hydrogen, fluorine, chlorine, bromine or methyl;
R
14选自甲基、乙基、正丙基、异丙基、异丁基或叔丁基；
R 14 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl or tert-butyl;
R
15选自甲基、环丙基或三氟甲基；
R 15 is selected from methyl, cyclopropyl or trifluoromethyl;
或，具有羧基的式(I)化合物的可农用盐或衍生物。Or, an agriculturally acceptable salt or derivative of a compound of formula (I) having a carboxyl group.
本发明更进一步再优选的化合物为：通式(I)中The further preferred compound of the present invention is: in the general formula (I)
R
1、R
2分别选自氢、氟或氯；
R 1 and R 2 are each selected from hydrogen, fluorine or chlorine;
R
3选自氢或C
1-C
4烷基；
R 3 is selected from hydrogen or C 1 -C 4 alkyl;
R
4选自氢、甲基、乙基、正丙基、异丙基或叔丁基；
R 4 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl or tert-butyl;
R
5选自氢、甲基、乙基、三氟甲基、CH
2CO
2CH
3、CH
2CO
2C
2H
5、CO
2CH
3、CO
2C
2H
5、CH
2SiC(CH
3)
3、未取代或被1-2个独立选自以下基团取代的苯基：氟、氯或溴；
R 5 is selected from hydrogen, methyl, ethyl, trifluoromethyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5 , CO 2 CH 3 , CO 2 C 2 H 5 , CH 2 SiC (CH 3 ) 3. Unsubstituted or substituted phenyl groups independently selected from the following groups: fluorine, chlorine or bromine;
R
6选自氢、氰基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、甲氧基、乙氧基、异丙氧基、叔丁氧基、环丙基、环戊基、环己基、CH
2CO
2CH
3、CH
2CO
2C
2H
5、CH
2CH
2CO
2CH
3、CH
2CH
2CO
2C
2H
5、CO
2R
7、CH
2OR
8、CONR
9R
10、未取代或被1-2个独立选自以下基团取代的苯基：氟、氯或溴；
R 6 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butyl Oxy, cyclopropyl, cyclopentyl, cyclohexyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5 , CH 2 CH 2 CO 2 CH 3 , CH 2 CH 2 CO 2 C 2 H 5 , CO 2 R 7 , CH 2 OR 8 , CONR 9 R 10 , unsubstituted or phenyl substituted with 1-2 independently selected from the following groups: fluorine, chlorine or bromine;
R
5、R
6可与相邻的C连接形成四氢呋喃酮环；
R 5 and R 6 can be connected with adjacent C to form a tetrahydrofuranone ring;
R
3、R
5可与相邻的C连接形成环戊烷或环己烷；
R 3 and R 5 can be connected with adjacent C to form cyclopentane or cyclohexane;
R
7选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、三氟乙基、二氟乙基、1-氯乙基、1-氟乙基、环丙基、环己基、烯丙基、炔丙基、甲氧基乙基、乙氧基乙基、乙酰氧基乙基、丙烯酰氧基乙基、甲基丙烯酰氧基、二甲氨基乙基、二异丙基氨基乙基、甲氨基乙基、乙氨基乙基、异丙氨基乙基、叔丁氨基乙基、四氢呋喃亚甲基、未取代或被1-2个独立选自以下基团取代的苯基：氟、氯或溴；
R 7 is selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, trifluoroethyl, difluoroethyl, 1-chloroethyl, 1- Fluoroethyl, cyclopropyl, cyclohexyl, allyl, propargyl, methoxyethyl, ethoxyethyl, acetoxyethyl, acryloxyethyl, methacryloxy , Dimethylaminoethyl, diisopropylaminoethyl, methylaminoethyl, ethylaminoethyl, isopropylaminoethyl, tert-butylaminoethyl, tetrahydrofuranmethylene, unsubstituted or 1-2 Independently selected from the phenyl substituted by the following groups: fluorine, chlorine or bromine;
R
8选自氢、C
1-C
4烷基羰基、C
1-C
4卤代烷基羰基、环丙甲酰基、C
1-C
4烷基磺酰基、C
1-C
4卤代烷基磺酰基、二(C
1-C
2)烷基氨基磺酰基、二(C
1-C
3)烷基氨基羰基、C
1-C
2烷硫基C
2-C
4烷基羰基、苯乙酰基、苯丙酰基、2-甲基-4-氯苯氧乙酰基、2,4-二氯苯氧乙酰基、
R 8 is selected from hydrogen, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, cyclopropanoyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, two (C 1 -C 2 )alkylaminosulfonyl, di(C 1 -C 3 )alkylaminocarbonyl, C 1 -C 2 alkylthio, C 2 -C 4 alkylcarbonyl, phenylacetyl, phenylpropionyl , 2-Methyl-4-chlorophenoxyacetyl, 2,4-dichlorophenoxyacetyl,
R
9选自氢、甲基、乙基、异丙基、正丙基、正丁基、叔丁基、三氟乙基、二氟乙基、1-氯乙基、1-氯丙基或2-氯丙基；
R 9 is selected from hydrogen, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, trifluoroethyl, difluoroethyl, 1-chloroethyl, 1-chloropropyl or 2-chloropropyl;
R
10选自氢、甲基、乙基、异丙基、正丙基、正丁基、叔丁基、甲氧基羰基亚甲基、乙氧基羰基亚甲基、SO
2NHCH
3、SO
2NHC
2H
5、SO
2N(CH
3)
2或SO
2N(CH
3)[CH(CH
3)
2]；
R 10 is selected from hydrogen, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, methoxycarbonylmethylene, ethoxycarbonylmethylene, SO 2 NHCH 3 , SO 2 NHC 2 H 5 , SO 2 N(CH 3 ) 2 or SO 2 N(CH 3 )[CH(CH 3 ) 2 ];
Q选自如下Q1、Q2、Q3、Q4、Q5、Q6、Q7或Q8；Q is selected from the following Q1, Q2, Q3, Q4, Q5, Q6, Q7 or Q8;
R
11选自甲基、乙基、异丙基、叔丁基、二氟甲基、三氟乙基或二氟乙基；
R 11 is selected from methyl, ethyl, isopropyl, tert-butyl, difluoromethyl, trifluoroethyl or difluoroethyl;
R
12选自甲基、三氟甲基、二氟甲基、甲氧基、异丙氧基、三氟甲氧基、二氟甲氧基、三氟乙氧基或者二氟乙氧基；
R 12 is selected from methyl, trifluoromethyl, difluoromethyl, methoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, trifluoroethoxy or difluoroethoxy;
R
13选自氢、氯、溴或甲基；
R 13 is selected from hydrogen, chlorine, bromine or methyl;
R
14选自甲基、乙基、正丙基、异丙基、异丁基或叔丁基；
R 14 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl or tert-butyl;
或，具有羧基的式(I)化合物的可农用盐或衍生物。Or, an agriculturally acceptable salt or derivative of a compound of formula (I) having a carboxyl group.
本发明最优选的化合物为：通式(I)中The most preferred compound of the present invention is: in the general formula (I)
R
1、R
2分别选自氢、氟或氯；
R 1 and R 2 are each selected from hydrogen, fluorine or chlorine;
R
3选自氢、甲基或乙基；
R 3 is selected from hydrogen, methyl or ethyl;
R
4选自氢或甲基；
R 4 is selected from hydrogen or methyl;
R
5选自氢、甲基、乙基、三氟甲基、CH
2CO
2CH
3、CH
2CO
2C
2H
5、CO
2CH
3、CO
2C
2H
5或CH
2SiC(CH
3)
3；
R 5 is selected from hydrogen, methyl, ethyl, trifluoromethyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5 , CO 2 CH 3 , CO 2 C 2 H 5 or CH 2 SiC (CH 3 ) 3 ;
R
6选自氢、氰基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、甲氧基、环丙基、CH
2CO
2CH
3、CH
2CO
2C
2H
5、CH
2CH
2CO
2CH
3、CH
2CH
2CO
2C
2H
5或CO
2R
7；
R 6 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, cyclopropyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5 , CH 2 CH 2 CO 2 CH 3 , CH 2 CH 2 CO 2 C 2 H 5 or CO 2 R 7 ;
R
5、R
6可与相邻的C连接形成四氢呋喃酮环；
R 5 and R 6 can be connected with adjacent C to form a tetrahydrofuranone ring;
R
3、R
5可与相邻的C连接形成环戊烷或环己烷；
R 3 and R 5 can be connected with adjacent C to form cyclopentane or cyclohexane;
R
7选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、三氟乙基、二氟乙基、1-氯乙基、1-氟乙基、环丙基、环己基、烯丙基、炔丙基、甲氧基乙基、乙氧基乙基、乙酰氧基乙基、丙烯酰氧基乙基、甲基丙烯酰氧基、二甲氨基乙基、二异丙基氨基乙基、甲氨基乙基、乙氨基乙基、异丙氨基乙基、叔丁氨基乙基、四氢呋喃亚甲基、未取代或被1-2个独立选自以下基团取代的苯基：氟、氯或溴。
R 7 is selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, trifluoroethyl, difluoroethyl, 1-chloroethyl, 1- Fluoroethyl, cyclopropyl, cyclohexyl, allyl, propargyl, methoxyethyl, ethoxyethyl, acetoxyethyl, acryloxyethyl, methacryloxy , Dimethylaminoethyl, diisopropylaminoethyl, methylaminoethyl, ethylaminoethyl, isopropylaminoethyl, tert-butylaminoethyl, tetrahydrofuranmethylene, unsubstituted or 1-2 Independently selected from phenyl substituted by the following groups: fluorine, chlorine or bromine.
Q选自如下Q1、Q2、Q3、Q4、Q5、Q6、Q7或Q8；Q is selected from the following Q1, Q2, Q3, Q4, Q5, Q6, Q7 or Q8;
R
11选自甲基或二氟甲基；
R 11 is selected from methyl or difluoromethyl;
R
12选自甲基、三氟甲基、二氟甲基、异丙氧基、二氟甲氧基、三氟乙氧基或者二氟乙氧基；
R 12 is selected from methyl, trifluoromethyl, difluoromethyl, isopropoxy, difluoromethoxy, trifluoroethoxy or difluoroethoxy;
R
13选自氯、溴或甲基；
R 13 is selected from chlorine, bromine or methyl;
R
14选自甲基、异丙基、异丁基或叔丁基；
R 14 is selected from methyl, isopropyl, isobutyl or tert-butyl;
或，具有羧基的式(I)化合物的可农用盐或衍生物。Or, an agriculturally acceptable salt or derivative of a compound of formula (I) having a carboxyl group.
上面给出的通式(I)化合物的定义中，汇集所用术语一般定义如下：In the definition of the compound of general formula (I) given above, the terms used in pooling are generally defined as follows:
卤素：指氟、氯、溴或碘。烷基：直链或支链烷基，例如甲基、乙基、丙基、异丙基、正丁基或叔丁基。环烷基：取代或未取代的环状烷基，例如环丙基、环戊基或环己基。取代基如甲基、卤素等。卤代烷基：直链或支链烷基，在这些烷基上的氢原子可部分或全部被卤原子所取代，例如，氯甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基等。烷氧基：直链或支链烷基，经氧原子键连接到结构上。卤代烷氧基：直链或支链烷氧基，在这些烷氧基上的氢原子可部分或全部被卤原子所取代。例如，氯甲氧基、二氯甲氧基、三氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氯氟甲氧基、三氟乙氧基等。烷硫基：直链或支链烷基，经硫原子键连接到结构上。卤代烷硫基：直链或支链烷硫基，在这些烷基上的氢原子可部分或全部被卤原子所取代。例如，氯甲硫基、二氯甲硫基、三氯甲硫基、氟甲硫基、二氟甲硫基、三氟甲硫基、氯氟甲硫基等。烯基：直链或支链烯类，例如乙烯基、1-丙烯基、2-丙烯基和不同的丁烯基、戊烯基和己烯基异构体。烯基还包括多烯类，如1,2-丙二烯基和2,4-己二烯基。烷基磺酰基：直链或支链烷基经磺酰基(-SO
2-)连接到结构上，如甲基磺酰基。卤代烷基磺酰基：直链或支链烷基磺酰基，其烷基上的氢原子可部分或全部被卤原子所取代。烷基亚磺酰基：直链或支链烷基经磺酰基(-SO-)连接到结构上，如甲基亚磺酰基。卤代烷基磺酰基：直链或支链烷基亚磺酰基，其烷基上的氢原子可部分或全部被卤原子所取代。烷氧基羰基：烷氧基经羰基连接到结构上，如CH
3OCO-或CH
3CH
2OCO-。烷氧基烷基：烷基-O-烷基-，如CH
3OCH
2-。烷羰基氧基烷氧基羰基：烷基-CO-O-烷基-OCO-，如CH
3COOCH
2OCO-、 CH
3COOCH
2CH
2OCO-或C
2H
5COOCH
2CH
2OCO-等。烷基羰基：烷基经羰基连接到结构上，如CH
3CO-或CH
3CH
2CO-等。卤代烷基羰基：卤代烷基经羰基连接到结构上，如CF
3CO-或CF
2HCO-等。环烷基羰基：环烷基经羰基连接到结构上，如环丙甲酰基或环己基甲酰基等。卤代环烷基羰基：卤代环烷基经羰基连接到结构上，如1-氯环丙甲酰基等。烷基氨基磺酰基：烷基-NH-SO
2-，如CH
3NHSO
2-或C
2H
5NHSO
2-等。二烷基氨基磺酰基：二烷基-N-SO
2-，如(CH
3)
2NSO
2-或(C
2H
5)
2NSO
2-等。烷基氨基羰基：烷基-NH-CO-，如CH
3NHCO-或C
2H
5NHCO-等。二烷基氨基羰基：二烷基-N-CO-，如(CH
3)
2NCO-或(C
2H
5)
2NCO-等。二烷基氨基硫代羰基：二烷基-N-CS-，如(CH
3)
2NCS-或(C
2H
5)
2NCS-等。烷硫基烷基羰基：烷基-S-烷基-CO，如CH
3SCH
2CO或CH
3SCH
2CH
2CO等。芳基：多元芳香基团，如苯基、萘基。杂芳基是含1个或多个N、O、S杂原子的五元环或六元环。例如呋喃基、吡唑基、噻唑基、吡啶基、嘧啶基、吡嗪基、哒嗪基、三嗪基、喹啉基等。SO
2NH(C
1-C
4烷基)：-SO
2NHCH
3或-SO
2NHC
2H
5等。SO
2N(C
1-C
2烷基)(C
1-C
4烷基)：-SO
2N(CH
3)
2或-SO
2N(CH
3)[CH(CH
3)
2]等。
Halogen: refers to fluorine, chlorine, bromine or iodine. Alkyl: straight or branched chain alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl or tert-butyl. Cycloalkyl: A substituted or unsubstituted cyclic alkyl group, such as cyclopropyl, cyclopentyl or cyclohexyl. Substituents such as methyl, halogen and the like. Halogenated alkyl groups: straight or branched chain alkyl groups. The hydrogen atoms on these alkyl groups can be partially or completely replaced by halogen atoms, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, dichloromethane Fluoromethyl, trifluoromethyl, etc. Alkoxy: straight or branched chain alkyl, connected to the structure via an oxygen atom bond. Halogenated alkoxy groups: straight-chain or branched-chain alkoxy groups. The hydrogen atoms on these alkoxy groups may be partially or completely replaced by halogen atoms. For example, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy and the like. Alkylthio: straight or branched chain alkyl group, connected to the structure via a sulfur atom bond. Halogenated alkylthio: linear or branched alkylthio. The hydrogen atoms on these alkyl groups can be partially or completely replaced by halogen atoms. For example, chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio and the like. Alkenyl: straight or branched chain alkenes, such as vinyl, 1-propenyl, 2-propenyl and the different butenyl, pentenyl and hexenyl isomers. Alkenyl also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. Alkylsulfonyl: A straight or branched chain alkyl group is connected to the structure via a sulfonyl group (-SO 2 -), such as a methylsulfonyl group. Halogenated alkylsulfonyl: linear or branched alkylsulfonyl, the hydrogen atoms on the alkyl group can be partially or completely replaced by halogen atoms. Alkylsulfinyl: A straight or branched chain alkyl group is connected to the structure via a sulfonyl group (-SO-), such as a methylsulfinyl group. Halogenated alkylsulfonyl: linear or branched alkylsulfinyl, the hydrogen atoms on the alkyl group can be partially or completely replaced by halogen atoms. Alkoxycarbonyl: The alkoxy is connected to the structure via a carbonyl group, such as CH 3 OCO- or CH 3 CH 2 OCO-. Alkoxyalkyl: alkyl-O-alkyl-, such as CH 3 OCH 2 -. Alkylcarbonyloxyalkoxycarbonyl: alkyl-CO-O-alkyl- OCO-, such as CH 3 COOCH 2 OCO-, CH 3 COOCH 2 CH 2 OCO- or C 2 H 5 COOCH 2 CH 2 OCO-, etc. . Alkylcarbonyl: The alkyl group is connected to the structure via the carbonyl group, such as CH 3 CO- or CH 3 CH 2 CO-. Haloalkylcarbonyl: The haloalkyl is connected to the structure via a carbonyl group, such as CF 3 CO- or CF 2 HCO-. Cycloalkylcarbonyl: Cycloalkyl is connected to the structure via carbonyl, such as cyclopropanoyl or cyclohexylformyl. Halogenated cycloalkylcarbonyl group: The halogenated cycloalkyl group is connected to the structure via a carbonyl group, such as 1-chlorocyclopropanoyl and the like. Alkylaminosulfonyl: alkyl -NH-SO 2 -, such as CH 3 NHSO 2 -or C 2 H 5 NHSO 2 -and so on. Dialkylaminosulfonyl: dialkyl-N-SO 2 -, such as (CH 3 ) 2 NSO 2 -or (C 2 H 5 ) 2 NSO 2 -, etc. Alkylaminocarbonyl: alkyl-NH-CO-, such as CH 3 NHCO- or C 2 H 5 NHCO- etc. Dialkylaminocarbonyl: dialkyl-N-CO-, such as (CH 3 ) 2 NCO- or (C 2 H 5 ) 2 NCO-, etc. Dialkylaminothiocarbonyl: dialkyl-N-CS-, such as (CH 3 ) 2 NCS- or (C 2 H 5 ) 2 NCS-, etc. Alkylthioalkylcarbonyl: alkyl-S-alkyl-CO, such as CH 3 SCH 2 CO or CH 3 SCH 2 CH 2 CO. Aryl: polyvalent aromatic groups, such as phenyl and naphthyl. Heteroaryl is a five-membered ring or six-membered ring containing one or more N, O, S heteroatoms. For example, furyl, pyrazolyl, thiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl and the like. SO 2 NH (C 1 -C 4 alkyl): -SO 2 NHCH 3 or -SO 2 NHC 2 H 5 and the like. SO 2 N(C 1 -C 2 alkyl) (C 1 -C 4 alkyl): -SO 2 N(CH 3 ) 2 or -SO 2 N(CH 3 )[CH(CH 3 ) 2 ], etc.
本发明的部分化合物可以用表1-表35中列出的具体化合物来说明，但本发明并不仅限于这些化合物。Part of the compounds of the present invention can be illustrated by specific compounds listed in Table 1 to Table 35, but the present invention is not limited to these compounds.
表1：通式I中，Q＝Q1，R
4＝H，R
11＝CH
3，R
12＝CF
3，R
13＝Cl，R
1、R
2、R
3、R
5、R
6具体见下表。
Table 1: Formula I, Q = Q1, R 4 = H, R 11 = CH 3, R 12 = CF 3, R 13 = Cl, R 1, R 2, R 3, R 5, R 6 , see particularly The following table.
表1Table 1
表2：通式I中，Q＝Q1，R
4＝H，R
11＝CH
3，R
12＝CF
3，R
13＝Br，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 2: Formula I, Q = Q1, R 4 = H, R 11 = CH 3, R 12 = CF 3, R 13 = Br, R 1, R 2, R 3, R 5, R 6 , see particularly Table 1.
表3：通式I中，Q＝Q1，R
4＝H，R
11＝CH
3，R
12＝OCH
3，R
13＝Cl，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 3: Formula I, Q = Q1, R 4 = H, R 11 = CH 3, R 12 = OCH 3, R 13 = Cl, R 1, R 2, R 3, R 5, R 6 , see particularly Table 1.
表4：通式I中，Q＝Q1，R
4＝H，R
11＝CH
3，R
12＝OCH
3，R
13＝Br，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 4: Formula I, Q = Q1, R 4 = H, R 11 = CH 3, R 12 = OCH 3, R 13 = Br, R 1, R 2, R 3, R 5, R 6 , see particularly Table 1.
表5：通式I中，Q＝Q1，R
4＝H，R
11＝CH
3，R
12＝OCHF
2，R
13＝Cl，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 5: Formula I, Q = Q1, R 4 = H, R 11 = CH 3, R 12 = OCHF 2, R 13 = Cl, R 1, R 2, R 3, R 5, R 6 , see particularly Table 1.
表6：通式I中，Q＝Q1，R
4＝H，R
11＝CH
3，R
12＝OCHF
2，R
13＝Br，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 6: Formula I, Q = Q1, R 4 = H, R 11 = CH 3, R 12 = OCHF 2, R 13 = Br, R 1, R 2, R 3, R 5, R 6 , see particularly Table 1.
表7：通式I中，Q＝Q1，R
4＝H，R
11＝CH
3，R
12＝OCH(CH
3)
2，R
13＝Cl，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 7: Formula I, Q = Q1, R 4 = H, R 11 = CH 3, R 12 = OCH (CH 3) 2, R 13 = Cl, R 1, R 2, R 3, R 5, R 6 is shown in Table 1 for details.
表8：通式I中，Q＝Q1，R
4＝H，R
11＝CH
3，R
12＝OCH(CH
3)
2，R
13＝Br，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 8: Formula I, Q = Q1, R 4 = H, R 11 = CH 3, R 12 = OCH (CH 3) 2, R 13 = Br, R 1, R 2, R 3, R 5, R 6 is shown in Table 1 for details.
表9：通式I中，Q＝Q1，R
4＝H，R
11＝CH
3，R
12＝OCF
3，R
13＝Cl，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 9: Formula I, Q = Q1, R 4 = H, R 11 = CH 3, R 12 = OCF 3, R 13 = Cl, R 1, R 2, R 3, R 5, R 6 , see particularly Table 1.
表10：通式I中，Q＝Q1，R
4＝H，R
11＝CH
3，R
12＝OCF
3，R
13＝Br，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 10: Formula I, Q = Q1, R 4 = H, R 11 = CH 3, R 12 = OCF 3, R 13 = Br, R 1, R 2, R 3, R 5, R 6 , see particularly Table 1.
表11：通式I中，Q＝Q1，R
4＝H，R
11＝CH
3，R
12＝OCH
2CF
3，R
13＝Cl，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 11: Formula I, Q = Q1, R 4 = H, R 11 = CH 3, R 12 = OCH 2 CF 3, R 13 = Cl, R 1, R 2, R 3, R 5, R 6 See Table 1 for details.
表12：通式I中，Q＝Q1，R
4＝H，R
11＝CH
3，R
12＝OCH
2CF
3，R
13＝Br，R
1、R
2、R
3、R
5、 R
6具体见表1。
Table 12: Formula I, Q = Q1, R 4 = H, R 11 = CH 3, R 12 = OCH 2 CF 3, R 13 = Br, R 1, R 2, R 3, R 5, R 6 See Table 1 for details.
表13：通式I中，Q＝Q1，R
4＝H，R
11＝CH
3，R
12＝CHF
2，R
13＝Cl，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 13: Formula I, Q = Q1, R 4 = H, R 11 = CH 3, R 12 = CHF 2, R 13 = Cl, R 1, R 2, R 3, R 5, R 6 , see particularly Table 1.
表14：通式I中，Q＝Q1，R
4＝H，R
11＝CH
3，R
12＝CHF
2，R
13＝Br，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 14: Formula I, Q = Q1, R 4 = H, R 11 = CH 3, R 12 = CHF 2, R 13 = Br, R 1, R 2, R 3, R 5, R 6 , see particularly Table 1.
表15：通式I中，Q＝Q2，R
4＝H，R
11＝CHF
2，R
12＝CH
3，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 15: Formula I, Q = Q2, R 4 = H, R 11 = CHF 2, R 12 = CH 3, R 1, R 2, R 3, R 5, R 6 See Table 1.
表16：通式I中，Q＝Q2，R
4＝H，R
11＝CH
3，R
12＝CF
3，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 16: Formula I, Q = Q2, R 4 = H, R 11 = CH 3, R 12 = CF 3, R 1, R 2, R 3, R 5, R 6 See Table 1.
表17：通式I中，Q＝Q3，R
4＝H，R
13＝Cl，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 17: Formula I, Q = Q3, R 4 = H, R 13 = Cl, R 1, R 2, R 3, R 5, R 6 See Table 1.
表18：通式I中，Q＝Q3，R
4＝H，R
13＝Br，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 18: Formula I, Q = Q3, R 4 = H, R 13 = Br, R 1, R 2, R 3, R 5, R 6 See Table 1.
表19：通式I中，Q＝Q4，R
4＝H，R
13＝Cl，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 19: Formula I, Q = Q4, R 4 = H, R 13 = Cl, R 1, R 2, R 3, R 5, R 6 See Table 1.
表20：通式I中，Q＝Q4，R
4＝H，R
13＝Br，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 20: Formula I, Q = Q4, R 4 = H, R 13 = Br, R 1, R 2, R 3, R 5, R 6 See Table 1.
表21：通式I中，Q＝Q5，R
4＝H，R
12＝CHF
2，R
13＝CH
3，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 21: Formula I, Q = Q5, R 4 = H, R 12 = CHF 2, R 13 = CH 3, R 1, R 2, R 3, R 5, R 6 See Table 1.
表22：通式I中，Q＝Q5，R
4＝H，R
12＝CF
3，R
13＝CH
3，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 22: Formula I, Q = Q5, R 4 = H, R 12 = CF 3, R 13 = CH 3, R 1, R 2, R 3, R 5, R 6 See Table 1.
表23：通式I中，Q＝Q5，R
4＝H，R
12＝CHF
2，R
13＝Cl，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 23: Formula I, Q = Q5, R 4 = H, R 12 = CHF 2, R 13 = Cl, R 1, R 2, R 3, R 5, R 6 See Table 1.
表24：通式I中，Q＝Q5，R
4＝H，R
12＝CF
3，R
13＝Br，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 24: Formula I, Q = Q5, R 4 = H, R 12 = CF 3, R 13 = Br, R 1, R 2, R 3, R 5, R 6 See Table 1.
表25：通式I中，Q＝Q6，R
4＝H，R
14＝C(CH
3)
3，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 25: Formula I, Q = Q6, R 4 = H, R 14 = C (CH 3) 3, R 1, R 2, R 3, R 5, R 6 See Table 1.
表26：通式I中，Q＝Q7，R
4＝H，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 26: In the general formula I, Q=Q7, R 4 =H, and R 1 , R 2 , R 3 , R 5 , and R 6 are detailed in Table 1.
表27：通式I中，Q＝Q8，R
4＝H，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 27: In the general formula I, Q=Q8, R 4 =H, and R 1 , R 2 , R 3 , R 5 , and R 6 are detailed in Table 1.
表28：通式I中，Q＝Q9，R
4＝H，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 28: In the general formula I, Q=Q9, R 4 =H, and R 1 , R 2 , R 3 , R 5 , and R 6 are detailed in Table 1.
表29：通式I中，Q＝Q10，R
4＝H，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 29: Formula I, Q = Q10, R 4 = H, R 1, R 2, R 3, R 5, R 6 See Table 1.
表30：通式I中，Q＝Q11，R
4＝H，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 30: Formula I, Q = Q11, R 4 = H, R 1, R 2, R 3, R 5, R 6 See Table 1.
表31：通式I中，Q＝Q12，R
4＝H，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 31: Formula I, Q = Q12, R 4 = H, R 1, R 2, R 3, R 5, R 6 See Table 1.
表32：通式I中，Q＝Q2，R
4＝H，R
11＝CH
3，R
12＝CH
3，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 32: Formula I, Q = Q2, R 4 = H, R 11 = CH 3, R 12 = CH 3, R 1, R 2, R 3, R 5, R 6 See Table 1.
表33：通式I中，Q＝Q13，R
4＝H，R
15＝CH
3，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 33: In the general formula I, Q=Q13, R 4 =H, R 15 =CH 3 , R 1 , R 2 , R 3 , R 5 , and R 6 are shown in Table 1.
表34：通式I中，Q＝Q13，R
4＝H，R
15＝CF
3，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 34: In the general formula I, Q=Q13, R 4 =H, R 15 =CF 3 , R 1 , R 2 , R 3 , R 5 , and R 6 are shown in Table 1.
表35：通式I中，Q＝Q13，R
4＝H，R
15＝环丙基，R
1、R
2、R
3、R
5、R
6具体见表1。
Table 35: In the general formula I, Q=Q13, R 4 =H, R 15 =cyclopropyl, R 1 , R 2 , R 3 , R 5 , and R 6 are shown in Table 1.
本发明通式I所示化合物的制备：Preparation of the compound represented by general formula I of the present invention:
当Q选自Q1、Q3和Q4时本发明化合物可为通式I-1所示化合物，其可借助文献描述的方法由肟基化合物III经过氯化合环得到，如J.Agric.Food Chem.2005,53,8639-8643、CN105753853、WO2006090234等。When Q is selected from Q1, Q3 and Q4, the compound of the present invention can be a compound represented by the general formula I-1, which can be obtained from the oxime-based compound III through chlorination ring closure by the method described in the literature, such as J.Agric.FoodChem. 2005,53,8639-8643, CN105753853, WO2006090234, etc.
肟基化合物III可借助文献描述方法由甲基中间体VI经过三氧化铬氧化得到中间体V经过脱羧得到醛基化合物IV，再经过羟胺肟化得到，如CN1402979、化学反应工程与工艺,2002,18(4),373-376、高等化学学报,2003,24(7),1225-1230等。The oxime compound III can be obtained from the methyl intermediate VI through the oxidation of chromium trioxide by the method described in the literature, and the intermediate V is obtained by decarboxylation to obtain the aldehyde compound IV, which is then obtained through hydroxamidoximation, such as CN1402979, Chemical Reaction Engineering and Technology, 2002, 18(4), 373-376, Journal of Advanced Chemistry, 2003, 24(7), 1225-1230, etc.
甲基中间体VI可由中间体VII经过NBS、Br
2、NCS或者Cl
2经过溴化或者氯化得到，亦可由中间体XIV与肼合环得到，具体可参照WO2015050040、WO9712884、WO9519967、US5861359、EP361114、Canadian Journal of Chemistry,1986,64(11),2211-19、高等化学学报,2003,24(7),1225-1230等。中间体VII可由VIII与肼合环得到或者通过X与肼合环再醚化得到，具体可参照Synthesis,(5),1986,409-11、Journal of Organic Chemistry,2008,73(9), 3523-3529、WO2015183839、CN101870677、CN1402979、高等化学学报,2003,24(7),1225-1230等。中间体VIII可由XI与R
2CO
2CH
3、R
2CO
2C
2H
5、(R
2CO)
2O或R
2COCl反应得到，中间体XIV可由XIII与R
2CO
2CH
3、R
2CO
2C
2H
5、(R
2CO)
2O或R
2COCl反应得到，具体可参照Bioorganic & Medicinal Chemistry,2018,26(12),3406-3413、Tetrahedron Letters,2016,57(14),1555-1559、Handbook on Herbicides,2014,263-276等。X可由XI与碳酸二甲酯或者碳酸二乙酯反应得到，具体可参照CN109422726、Research on Chemical Intermediates,2012,38(9),2355-2363等。中间体XI、XIII可由XII由傅克反应得到，具体可参照US20140073631等。
Methyl intermediate VI can be obtained from intermediate VII through bromination or chlorination of NBS, Br 2 , NCS or Cl 2 , or from intermediate XIV and hydrazine ring. For details, refer to WO2015050040, WO9712884, WO9519967, US5861359, EP361114 , Canadian Journal of Chemistry, 1986, 64(11), 2211-19, Journal of Advanced Chemistry, 2003, 24(7), 1225-1230, etc. Intermediate VII can be obtained by VIII and hydrazine ring or by re-etherification of X and hydrazine ring. For details, please refer to Synthesis, (5), 1986, 409-11, Journal of Organic Chemistry, 2008, 73(9), 3523 -3529, WO2015183839, CN101870677, CN1402979, Journal of Advanced Chemistry, 2003, 24(7), 1225-1230, etc. Intermediate VIII can be obtained by reacting XI with R 2 CO 2 CH 3 , R 2 CO 2 C 2 H 5 , (R 2 CO) 2 O or R 2 COCl, and intermediate XIV can be obtained from XIII and R 2 CO 2 CH 3 , R 2 CO 2 C 2 H 5 , (R 2 CO) 2 O or R 2 COCl reaction, please refer to Bioorganic & Medicinal Chemistry, 2018, 26(12), 3406-3413, Tetrahedron Letters, 2016, 57(14) , 1555-1559, Handbook on Herbicides, 2014, 263-276, etc. X can be obtained by reacting XI with dimethyl carbonate or diethyl carbonate. For details, refer to CN109422726, Research on Chemical Intermediates, 2012, 38(9), 2355-2363, etc. Intermediates XI and XIII can be obtained from XII by Friedel-Crafts reaction. For details, please refer to US20140073631 and the like.
当Q选自Q2、Q7和Q8时，本发明化合物可为通式I-2所示化合物，其可借助文献描述的方法，经过中间体XVI与乙酸酐或乙酰氯反应再合环得到，具体可参考Journal of Heterocyclic Chemistry,1987,24(5),1391-6、WO8501637和WO2000034249；当Q选自Q6时，本发明化合物可为通式I-3化合物，其可借助文献描述方法由中间体XVI经过两步得到，具体文献可参考US5728651或DE19601189；当Q选自Q5时本发明化合物可为通式I-4所示化合物，其可借助文献描述方法由中间体XVI经过两步得到，具体文献可参考EP860435、WO9817632、Organic Process Research & Development(2001),5(6),593-598或EP448188。When Q is selected from Q2, Q7, and Q8, the compound of the present invention can be a compound represented by the general formula I-2, which can be obtained by reacting intermediate XVI with acetic anhydride or acetyl chloride with the aid of the method described in the literature, and specifically Refer to the Journal of Heterocyclic Chemistry, 1987, 24(5), 1391-6, WO8501637 and WO2000034249; when Q is selected from Q6, the compound of the present invention may be a compound of general formula I-3, which can be obtained from intermediates by the method described in the literature XVI is obtained in two steps. For specific documents, please refer to US5728651 or DE19601189; when Q is selected from Q5, the compound of the present invention can be a compound represented by the general formula I-4, which can be obtained from intermediate XVI in two steps by means of the method described in the literature. Literature can refer to EP860435, WO9817632, Organic Process Research & Development (2001), 5(6), 593-598 or EP448188.
当Q选自Q9、Q10、Q11、Q12和Q13时，本发明通式I化合物可借助参考文献描述方法，先通过中间体XV与光气或者硫代光气形成异氰酸酯或者硫代异氰酸酯再与六氢哒嗪、2-羟基-3-甲基-3-丁烯酸乙酯、顺式-4-羟基-D-脯氨酸等合环得到，具体可参考当代化工,2003,32(1),18-19、WO8702357、WO2012041789、WO9837065、CN102286005、CN1401648、EP273417和US5223018。When Q is selected from Q9, Q10, Q11, Q12 and Q13, the compound of general formula I of the present invention can be described by reference to the method, first through intermediate XV and phosgene or thiophosgene to form isocyanate or thioisocyanate and then with six Hydropyridazine, 2-hydroxy-3-methyl-3-butenoic acid ethyl ester, cis-4-hydroxy-D-proline, etc. can be obtained by ring closure. For details, please refer to Contemporary Chemical Industry, 2003, 32(1) , 18-19, WO8702357, WO2012041789, WO9837065, CN102286005, CN1401648, EP273417 and US5223018.
中间体XV的制备可参照CN105753853得到。The preparation of intermediate XV can be obtained with reference to CN105753853.
除另有注明外，反应式中各基团定义同前。Unless otherwise noted, the definitions of the groups in the reaction formula are the same as before.
本发明的化合物可以有效地控制稗草、狗尾草、异型莎草、水莎草、马唐、荩草、苘麻、百日草、反枝苋、马齿苋、苍耳、龙葵、决明、野西瓜苗、野大豆等杂草，在低剂量下就可以获得很好的效果。对小麦、玉米、水稻具有一定的安全性，在农业上可用作除草剂。因此本发明还包括通式(I)化合物用于控制杂草的用途。The compound of the present invention can effectively control barnyardgrass, setaria, alien sedge, cyperus, crabgrass, shepherd's purse, velvetleaf, zinnia, amaranth, purslane, cocklebur, nightshade, cassia , Wild watermelon seedlings, wild soybeans and other weeds, good results can be obtained at low doses. It has certain safety to wheat, corn and rice, and can be used as a herbicide in agriculture. Therefore, the present invention also includes the use of compounds of general formula (I) for controlling weeds.
此外，本发明通式(I)化合物也适用于植物的干燥和/或脱叶。In addition, the compounds of the general formula (I) of the present invention are also suitable for drying and/or defoliating plants.
以下具体实施例用来进一步说明本发明，但本发明绝非限于这些例子。(除另有注明外，所用原料均有市售)The following specific examples are used to further illustrate the present invention, but the present invention is by no means limited to these examples. (Unless otherwise specified, all raw materials used are commercially available)
合成实施例Synthesis Example
实施例1 化合物1-12的制备Example 1 Preparation of Compound 1-12
1)2-氟-4-氯-5-甲基苯乙酮的制备1) Preparation of 2-fluoro-4-chloro-5-methylacetophenone
将22.9g(0.1585mol)2-氯-4-氟-甲苯、45.8g(0.344mol)无水三氯化铝依次加入到反应瓶中，室温搅拌下滴加18.7g(0.2382mol)乙酰氯，经半个小时滴加完毕，升温至50℃反应，形成褐色粘稠物，保持15小时后，冷至室温，倒入冰水中，二氯甲烷萃取，合并有机相，饱和食盐水洗涤两次，无水硫酸镁干燥有机相，过滤减压脱溶，柱层析(乙酸乙酯：石油醚＝1：10)得到27.4g油状物。22.9g (0.1585mol) 2-chloro-4-fluoro-toluene and 45.8g (0.344mol) anhydrous aluminum trichloride were sequentially added to the reaction flask, and 18.7g (0.2382mol) acetyl chloride was added dropwise with stirring at room temperature, After half an hour, the dripping was completed, the temperature was raised to 50°C to react, and a brown viscous substance was formed. After 15 hours, it was cooled to room temperature, poured into ice water, extracted with dichloromethane, combined the organic phases, and washed twice with saturated brine. The organic phase was dried with anhydrous magnesium sulfate, filtered and decompressed to remove the solvent, and column chromatography (ethyl acetate: petroleum ether = 1:10) to obtain 27.4 g of oil.
2)1-(4-氯-2-氟-5-甲基苯基)-4,4,4-三氟乙酰-1,3-丁二酮的制备2) Preparation of 1-(4-chloro-2-fluoro-5-methylphenyl)-4,4,4-trifluoroacetyl-1,3-butanedione
将27.4g(0.147mol)2-氟-4-氯-5-甲基苯乙酮、33.4g(0.22mol)三氟乙酸乙酯依次加入到装有150ml甲醇的反应瓶中室温搅拌，滴加88.2g(0.45mol)27％的甲醇钠溶液，升至回流反应1小时，冷至室温，将反应物倒入装有盐酸的冰水中，抽滤，水洗、干燥得浅黄色固体38.5g。熔点62-63℃。Add 27.4g (0.147mol) 2-fluoro-4-chloro-5-methylacetophenone and 33.4g (0.22mol) ethyl trifluoroacetate into a reaction flask containing 150ml methanol, stirring at room temperature, and adding dropwise 88.2g (0.45mol) of 27% sodium methoxide solution was heated to reflux for 1 hour, cooled to room temperature, the reactant was poured into ice water containing hydrochloric acid, filtered with suction, washed with water, and dried to obtain 38.5g of light yellow solid. Melting point 62-63°C.
3)3-(4-氯-2-氟-5-甲基苯基)-5-三氟甲基-1H-吡唑的制备3) Preparation of 3-(4-chloro-2-fluoro-5-methylphenyl)-5-trifluoromethyl-1H-pyrazole
将37g(0.131mol)1-(4-氯-2-氟-5-甲基苯基)-4,4,4-三氟乙酰-1,3-丁二酮溶于150ml乙酸中，一次性加入18.3g(0.293mol)85％水合肼，升至回流，反应20分钟，冷却至室温，倒入冰水中，过滤得白色固体33g。Dissolve 37g (0.131mol) 1-(4-chloro-2-fluoro-5-methylphenyl)-4,4,4-trifluoroacetyl-1,3-butanedione in 150ml acetic acid, one time Add 18.3g (0.293mol) of 85% hydrazine hydrate, raise to reflux, react for 20 minutes, cool to room temperature, pour into ice water, and filter to obtain 33g of white solid.
4)3-(4-氯-2-氟-5-甲基苯基)-1-甲基-5-三氟甲基-1H-吡唑的制备4) Preparation of 3-(4-chloro-2-fluoro-5-methylphenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole
将6g(0.02154mol)3-(4-氯-2-氟-5-甲基苯基)-5-三氟甲基-1H-吡唑、4.1g(0.03231mol)硫酸二甲酯加入到100毫升甲苯中，升温回流分出低沸点馏分，回流4小时，冷至室温，加入100毫升2.5N氢氧化钠溶液，分出有机相，饱和食盐水洗，经无水硫酸镁干燥，蒸除甲苯，加入80％乙醇重结晶，得浅黄色固体6.5g，熔点51-52℃。Add 6g (0.02154mol) 3-(4-chloro-2-fluoro-5-methylphenyl)-5-trifluoromethyl-1H-pyrazole, 4.1g (0.03231mol) dimethyl sulfate to 100 In ml of toluene, heat and reflux to separate the low-boiling fractions, reflux for 4 hours, cool to room temperature, add 100 ml of 2.5N sodium hydroxide solution, separate the organic phase, wash with saturated brine, dry over anhydrous magnesium sulfate, evaporate toluene, It was recrystallized by adding 80% ethanol to obtain 6.5 g of light yellow solid with a melting point of 51-52°C.
5)4-氯-3-(4-氯-2-氟-5-甲基苯基)-1-甲基-5-三氟甲基-1H-吡唑的制备5) Preparation of 4-chloro-3-(4-chloro-2-fluoro-5-methylphenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole
将3.58g(0.0122mol)3-(4-氯-2-氟-5-甲基苯基)-1-甲基-5-三氟甲基-1H-吡唑加入到装有50毫升DMF的反应瓶中，升温至60℃，分批加入3.34g(0.025mol)NCS，随后升温至80℃，在该温度下保持4小时，降至室温，倒入水，50ml乙酸乙酯萃取两次，合并有机相，饱和食盐水洗2次，无水硫酸镁干燥，脱溶，80％乙醇重结晶得浅黄色固体3.8g。熔点72-74℃。Add 3.58g (0.0122mol) 3-(4-chloro-2-fluoro-5-methylphenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole to 50 ml DMF In the reaction flask, the temperature was raised to 60°C, 3.34g (0.025mol) of NCS was added in batches, and then the temperature was raised to 80°C, kept at this temperature for 4 hours, and dropped to room temperature, poured into water, and extracted twice with 50ml ethyl acetate. The organic phases were combined, washed twice with saturated brine, dried with anhydrous magnesium sulfate, desolvated, and recrystallized with 80% ethanol to obtain 3.8 g of light yellow solid. Melting point 72-74°C.
6)2-氯-5-(4-氯-1-甲基-5-三氟甲基-1H-3-吡唑基)-4-氟苯甲缩醛二乙酸酯的制备6) Preparation of 2-chloro-5-(4-chloro-1-methyl-5-trifluoromethyl-1H-3-pyrazolyl)-4-fluorobenzaldehyde diacetate
将3.8g(0.0116mol)4-氯-3-(4-氯-2-氟-5-甲基苯基)-1-甲基-5-三氟甲基-1H-吡唑加入到10毫升乙酸和28毫升乙酸酐的混合液中，冰浴下滴加3.5毫升浓硫酸，分批加入2g(0.0201mol)三氧化铬，保持温度在10-15℃10小时，倒入冰水中，过滤得浅黄色固体3.7g。熔点135-136℃。Add 3.8g (0.0116mol) 4-chloro-3-(4-chloro-2-fluoro-5-methylphenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole to 10ml To the mixture of acetic acid and 28 ml of acetic anhydride, add 3.5 ml of concentrated sulfuric acid dropwise under an ice bath, add 2g (0.0201mol) of chromium trioxide in batches, keep the temperature at 10-15℃ for 10 hours, pour into ice water, and filter to obtain Light yellow solid 3.7g. Melting point 135-136°C.
7)2-氯-5-(4-氯-1-甲基-5-三氟甲基-1H-3-吡唑基)-4-氟苯甲醛的制备7) Preparation of 2-chloro-5-(4-chloro-1-methyl-5-trifluoromethyl-1H-3-pyrazolyl)-4-fluorobenzaldehyde
[根据细则91更正 26.10.2020]
将3.7g(0.0083mol)2-氯-5-(4-氯-1-甲基-5-三氟甲基-1H-3-吡唑基)-4-氟苯甲缩醛二乙酸酯和3.85g(0.046mol)碳酸氢钠依次加入到装有25ml乙醇和5毫升水的混合液中，升至回流反应2小时，倒入水中，过滤、干燥得浅黄色固体2.63g。熔点70-72℃。[Corrected according to Rule 91 26.10.2020]
3.7g (0.0083mol) 2-chloro-5-(4-chloro-1-methyl-5-trifluoromethyl-1H-3-pyrazolyl)-4-fluorobenzaldehyde diacetate And 3.85g (0.046mol) sodium bicarbonate were sequentially added to the mixed solution containing 25ml ethanol and 5ml water, raised to reflux and reacted for 2 hours, poured into water, filtered and dried to obtain 2.63g light yellow solid. The melting point is 70-72°C.
将3.7g(0.0083mol)2-氯-5-(4-氯-1-甲基-5-三氟甲基-1H-3-吡唑基)-4-氟苯甲缩醛二乙酸酯和3.85g(0.046mol)碳酸氢钠依次加入到装有25ml乙醇和5毫升水的混合液中，升至回流反应2小时，倒入水中，过滤、干燥得浅黄色固体2.63g。熔点70-72℃。[Corrected according to Rule 91 26.10.2020]
3.7g (0.0083mol) 2-chloro-5-(4-chloro-1-methyl-5-trifluoromethyl-1H-3-pyrazolyl)-4-fluorobenzaldehyde diacetate And 3.85g (0.046mol) sodium bicarbonate were sequentially added to the mixed solution containing 25ml ethanol and 5ml water, raised to reflux and reacted for 2 hours, poured into water, filtered and dried to obtain 2.63g light yellow solid. The melting point is 70-72°C.
8)2-氯-5-(4-氯-1-甲基-5-三氟甲基-1H-3-吡唑基)-4-氟苯甲醛肟的制备8) Preparation of 2-chloro-5-(4-chloro-1-methyl-5-trifluoromethyl-1H-3-pyrazolyl)-4-fluorobenzaldehyde oxime
将2.63g(0.0077mol)2-氯-5-(4-氯-1-甲基-5-三氟甲基-1H-3-吡唑基)-4-氟苯甲醛加入到25毫升乙醇中，滴加0.8g(0.011mol)盐酸羟胺和5毫升水的混合液，室温搅拌3小时，过滤得白色固体2.65g。熔点163-165℃。Add 2.63g (0.0077mol) 2-chloro-5-(4-chloro-1-methyl-5-trifluoromethyl-1H-3-pyrazolyl)-4-fluorobenzaldehyde to 25ml ethanol , The mixture of 0.8g (0.011mol) hydroxylamine hydrochloride and 5ml water was added dropwise, stirred at room temperature for 3 hours, and filtered to obtain 2.65g of white solid. Melting point 163-165°C.
9)2-氯-5-(4-氯-1-甲基-5-三氟甲基-1H-3-吡唑基)-4-氟苯甲醛氯肟的制备9) Preparation of 2-chloro-5-(4-chloro-1-methyl-5-trifluoromethyl-1H-3-pyrazolyl)-4-fluorobenzaldehyde chlorooxime
[根据细则91更正 26.10.2020]
将2.6g(0.0073mol)2-氯-5-(4-氯-1-甲基-5-三氟甲基-IH-3-吡唑基)-4-氟苯甲醛肟加入到50ml DMF中，升至60℃，分批加入1.1g(0.0077mol)NCS，保持1小时，冷至室温，加入100ml二氯甲烷，随后加入1N盐酸100ml，有机相随后用100ml饱和食盐水、100ml水洗，无水硫酸镁干燥，二氯甲烷溶液直接用于下一步。[Corrected according to Rule 91 26.10.2020]
2.6g (0.0073mol) 2-chloro-5-(4-chloro-1-methyl-5-trifluoromethyl-IH-3-pyrazolyl)-4-fluorobenzaldehyde oxime was added to 50ml DMF , Increase to 60℃, add 1.1g (0.0077mol) NCS in batches, keep it for 1 hour, cool to room temperature, add 100ml dichloromethane, then add 100ml 1N hydrochloric acid, and then wash the organic phase with 100ml saturated brine and 100ml water. The water was dried over magnesium sulfate, and the dichloromethane solution was used directly in the next step.
将2.6g(0.0073mol)2-氯-5-(4-氯-1-甲基-5-三氟甲基-IH-3-吡唑基)-4-氟苯甲醛肟加入到50ml DMF中，升至60℃，分批加入1.1g(0.0077mol)NCS，保持1小时，冷至室温，加入100ml二氯甲烷，随后加入1N盐酸100ml，有机相随后用100ml饱和食盐水、100ml水洗，无水硫酸镁干燥，二氯甲烷溶液直接用于下一步。[Corrected according to Rule 91 26.10.2020]
2.6g (0.0073mol) 2-chloro-5-(4-chloro-1-methyl-5-trifluoromethyl-IH-3-pyrazolyl)-4-fluorobenzaldehyde oxime was added to 50ml DMF , Increase to 60℃, add 1.1g (0.0077mol) NCS in batches, keep it for 1 hour, cool to room temperature, add 100ml dichloromethane, then add 100ml 1N hydrochloric acid, and then wash the organic phase with 100ml saturated brine and 100ml water. The water was dried over magnesium sulfate, and the dichloromethane solution was used directly in the next step.
10)化合物1-12的制备10) Preparation of compounds 1-12
将含有1g(0.00257mol)2-氯-5-(4-氯-1-甲基-5-三氟甲基-1H-3-吡唑基)-4-氟苯甲醛氯肟的二氯甲烷溶液置于冰浴中，滴加0.22g(0.003mol)2-甲氧基丙烯和0.76g(0.0075mol)的混合液，RT搅拌2小时。TLC监测反应完全，倒入水中，乙酸乙酯萃取，饱和食盐水洗，有机相无水硫酸镁干燥，减压脱溶，柱层析(乙酸乙酯：石油醚＝1:10)得0.81g油状物。Dichloromethane containing 1g (0.00257mol) 2-chloro-5-(4-chloro-1-methyl-5-trifluoromethyl-1H-3-pyrazolyl)-4-fluorobenzaldehyde chlorooxime The solution was placed in an ice bath, and a mixture of 0.22g (0.003mol) 2-methoxypropene and 0.76g (0.0075mol) was added dropwise, and stirred at RT for 2 hours. TLC monitors that the reaction is complete, pour into water, extract with ethyl acetate, wash with saturated brine, dry the organic phase with anhydrous magnesium sulfate, desolvate under reduced pressure, and column chromatography (ethyl acetate: petroleum ether = 1:10) to obtain 0.81 g of oil Things.
1H-NMR(300MHz，内标TMS，溶剂CDCl
3)δ(ppm):7.86(d,J＝7.5Hz,1H),7.31(d,J＝9.2Hz,1H),4.27(q,J＝7.1,2H),4.06(s,3H),3.99(d,J＝17.3Hz,1H),3.39(d,J＝17.3Hz,1H),1.72(s,3H),1.33(t,J＝7.1Hz,3H)。
1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 ) δ (ppm): 7.86 (d, J = 7.5 Hz, 1H), 7.31 (d, J = 9.2 Hz, 1H), 4.27 (q, J = 7.1,2H),4.06(s,3H),3.99(d,J=17.3Hz,1H), 3.39(d,J=17.3Hz,1H),1.72(s,3H),1.33(t,J=7.1 Hz, 3H).
参照实施例1中化合物1-12的合成，在第10)步将2-甲氧基丙烯分别替换为4-甲基-4-戊烯酸乙酯、甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸正丁酯、甲基丙烯酸异丙酯、甲基丙烯酸叔丁酯、甲基丙烯酸甲氧基乙酯、甲基丙烯酸二甲氨乙酯、甲基丙烯酸四氢糠基酯、2-甲烯基丁内酯、2-(三甲硅烷基甲基)丙烯酸乙酯、丙烯酸甲酯、丙烯酸乙酯、衣康酸二乙酯可分别得到化合物1-16、1-18、1-19、1-21、1-23、1-24、1-29、1-40、1-42、1-124、1-126、1-194、1-195、1-301。With reference to the synthesis of compounds 1-12 in Example 1, in step 10), 2-methoxypropene was replaced with 4-methyl-4-ethyl pentenoate, methyl methacrylate, and ethyl methacrylate. Ester, n-butyl methacrylate, isopropyl methacrylate, tert-butyl methacrylate, methoxyethyl methacrylate, dimethylaminoethyl methacrylate, tetrahydrofurfuryl methacrylate, 2-Methylbutyrolactone, 2-(trimethylsilylmeth)ethyl acrylate, methyl acrylate, ethyl acrylate, and diethyl itaconate can be used to obtain compounds 1-16, 1-18, 1- 19, 1-21, 1-23, 1-24, 1-29, 1-40, 1-42, 1-124, 1-126, 1-194, 1-195, 1-301.
参照实施例1中化合物1-12的合成，在第5)步将NCS替换成NBS，则得到化合物2-12，同时在第10)步将2-甲氧基丙烯分别替换为异丁烯、4-甲基-4-戊烯酸乙酯、甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸异丙酯、乙二醇二甲基丙烯酸酯、甲基丙烯酸苯酯、甲基丙烯酸异丁酯、2-(叔丁基氨基)甲基丙烯酸乙酯、甲基丙烯酸四氢糠基酯、N-叔丁基甲基丙烯酰胺、2-甲烯基丁内酯、2-(三甲硅烷基甲基)丙烯酸乙酯、三氟甲基丙烯酸甲酯、1-环己烯-1-甲酸甲酯、丙烯酸甲酯、丙烯酸乙酯、丙烯酸异丁酯、丙烯酸二甲氨乙酯可分别得到化合物2-1、2-16、2-18、2-19、2-23、2-27、2-32、2-39、2-41、2-42、2-52、2-124、2-126、2-160、2-173、2-194、2-195、2-214、2-215。Referring to the synthesis of compound 1-12 in Example 1, NCS was replaced with NBS in step 5), and compound 2-12 was obtained. At the same time, in step 10), 2-methoxypropene was replaced with isobutylene and 4- Ethyl methyl-4-pentenoate, methyl methacrylate, ethyl methacrylate, isopropyl methacrylate, ethylene glycol dimethacrylate, phenyl methacrylate, isobutyl methacrylate Ester, 2-(tert-butylamino) ethyl methacrylate, tetrahydrofurfuryl methacrylate, N-tert-butylmethacrylamide, 2-methylenylbutyrolactone, 2-(trimethylsilylmethyl) ) Ethyl acrylate, methyl trifluoromethacrylate, 1-cyclohexene-1-methyl methacrylate, methyl acrylate, ethyl acrylate, isobutyl acrylate, and dimethylaminoethyl acrylate can respectively give compound 2- 1, 2-16, 2-18, 2-19, 2-23, 2-27, 2-32, 2-39, 2-41, 2-42, 2-52, 2-124, 2-126, 2-160, 2-173, 2-194, 2-195, 2-214, 2-215.
部分化合物的物性和核磁数据见表36。The physical properties and nuclear magnetic data of some compounds are shown in Table 36.
表36Table 36
生物活性测定Biological activity determination
实施例2 室内除草活性测定Example 2 Indoor herbicidal activity determination
本发明化合物的除草活性测试方法如下：The herbicidal activity test method of the compound of the invention is as follows:
将定量的禾本科杂草(稗草、金色狗尾草)和阔叶杂草(百日草、苘麻)种子分别播于直径为7cm的装有营养土的纸杯中，播后覆土1cm，镇压、淋水后在温室按常规方法培养。禾本科杂草长至2～3叶期、阔叶杂草2～4叶期茎叶喷雾处理；苗前土壤喷雾处理于播种后24小时进行。按试验设计剂量，在履带式作物喷雾机(英国Engineer Research Ltd.设计生产)上进行喷雾处理(喷雾压力1.95kg/cm
2，喷液量500L/hm
2，履带速度1.48km/h)。试验设3次重复。试材处理后置于操作大厅，待药液自然阴干后，放于温室内按常规方法管理，观察并记录杂草对药剂的反应情况，处理后定期目测供试药剂对杂草的防除效果。
Sown quantitative gramineous weeds (barnyard grass, golden foxtail) and broadleaf weeds (zinnia, abutilon) seeds in a 7cm diameter paper cup filled with nutrient soil, and cover with 1cm soil after sowing to suppress, After being sprayed with water, it is cultivated in the greenhouse according to the conventional method. The gramineous weeds grow to the 2 to 3 leaf stage, and the broad-leaved weeds grow to the 2 to 4 leaf stage stem and leaf spray treatment; the pre-emergence soil spray treatment is carried out 24 hours after sowing. According to the test design dose, spray treatment (spray pressure 1.95kg/cm 2 , spray volume 500L/hm 2 , crawler speed 1.48km/h) on a crawler crop sprayer (designed and produced by British Engineer Research Ltd.). The test is set to be repeated 3 times. After the test materials are processed, they are placed in the operation hall. After the liquid is naturally dried in the shade, it is placed in the greenhouse for management according to conventional methods. Observation and recording of the weeds' response to the medicament is carried out. After treatment, the test medicament's control effect on weeds is regularly visually inspected.
防除效果分级标准：0为无效，100％为将杂草完全杀死或严重抑制。The control effect classification standard: 0 means invalid, 100% means complete kill or severe suppression of weeds.
经除草活性测试化合物1-12、1-16、1-18、1-19、1-21、1-23、1-24、1-29、1-40、1-42、1-124、1-126、1-194、1-195、1-301、2-1、2-12、2-16、2-18、2-19、2-23、2-27、2-32、2-39、2-41、2-42、2-52、2-124、2-126、2-160、2-173、2-194、2-195、2-214、2-215等在600g a.i./hm
2剂量下，苗前、苗后处理对百日草、苘麻、狗尾草及稗草除草活性均在85％以上，表现出较高活性。
Tested for herbicidal activity Compounds 1-12, 1-16, 1-18, 1-19, 1-21, 1-23, 1-24, 1-29, 1-40, 1-42, 1-124, 1 -126, 1-194, 1-195, 1-301, 2-1, 2-12, 2-16, 2-18, 2-19, 2-23, 2-27, 2-32, 2-39 , 2-41, 2-42, 2-52, 2-124, 2-126, 2-160, 2-173, 2-194, 2-195, 2-214, 2-215, etc. at 600g ai/hm At 2 doses, the herbicidal activity of pre-emergence and post-emergence treatments on Zinnia, Abutilon, Setaria and Barnyardgrass were all over 85%, showing higher activity.
进一步的活性测试结果见表37(所有质量浓度均以有效成分计)。Further activity test results are shown in Table 37 (all mass concentrations are based on active ingredients).
表37 部分化合物除草活性结果Table 37 Herbicidal activity results of some compounds
本发明化合物与CK-3、CK-4的苗后除草对比试验结果见表38(所有质量浓度均以有效成分计)。The post-emergence weeding comparison test results of the compound of the present invention and CK-3 and CK-4 are shown in Table 38 (all mass concentrations are calculated as effective ingredients).
表38 部分化合物除草活性结果Table 38 Herbicidal activity results of some compounds
Claims (8)
- 一种苯基异恶唑啉类化合物，如通式(I)所示：A kind of phenylisoxazoline compound, as shown in general formula (I):
式中：Where:R 1、R 2分别选自氢、卤素或C 1-C 6烷基； R 1 and R 2 are each selected from hydrogen, halogen or C 1 -C 6 alkyl;R 3选自氢、氰基、C 1-C 6烷基、苯基或被1-4个独立选自以下基团取代的苯基：卤素、CN、NO 2、C 1-C 6烷基、C 1-C 6卤代烷基、C 1-C 6烷氧基、C 1-C 6卤代烷氧基、C 1-C 6烷氧基羰基、C 1-C 6烷硫基或C 1-C 6烷基磺酰基； R 3 is selected from hydrogen, cyano, C 1 -C 6 alkyl, phenyl, or phenyl substituted with 1-4 independently selected from the group consisting of halogen, CN, NO 2 , C 1 -C 6 alkyl , C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio or C 1 -C 6 alkylsulfonyl;R 4选自氢、氰基、C 1-C 6烷基、CO 2R 7或CH 2OR 8； R 4 is selected from hydrogen, cyano, C 1 -C 6 alkyl, CO 2 R 7 or CH 2 OR 8 ;R 5选自氢、氰基、C 1-C 6烷基、C 1-C 6烷氧基、C 1-C 6卤代烷基、C 1-C 6烷基CO 2R 7、CO 2R 8、CH 2SiC[三(C 1-C 6烷基)]、未取代或被1-4个独立选自以下基团取代的苯基，以下基团为：卤素、CN、NO 2、C 1-C 6烷基、C 1-C 6卤代烷基、C 1-C 6烷氧基、C 1-C 6卤代烷氧基、C 1-C 6烷氧基羰基、C 1-C 6烷硫基或C 1-C 6烷基磺酰基； R 5 is selected from hydrogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 alkyl CO 2 R 7 , CO 2 R 8 , CH 2 SiC [three (C 1 -C 6 alkyl)], unsubstituted or phenyl substituted with 1-4 independently selected from the following groups, the following groups are: halogen, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio Or C 1 -C 6 alkylsulfonyl;R 6选自氢、氰基、C 1-C 6烷基、C 1-C 6烷氧基、C 1-C 6卤代烷基、C 3-C 6环烷基、C 1-C 6烷基CO 2R 7、CO 2R 7、CH 2OR 8、CH 2NR 9R 10、CONR 9R 10、未取代或被1-4个独立选自以下基团取代的苯基,以下基团为：卤素、CN、NO 2、C 1-C 6烷基、C 1-C 6卤代烷基、C 1-C 6烷氧基、C 1-C 6卤代烷氧基、C 1-C 6烷氧基羰基、C 1-C 6烷硫基或C 1-C 6烷基磺酰基； R 6 is selected from hydrogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkyl CO 2 R 7 , CO 2 R 7 , CH 2 OR 8 , CH 2 NR 9 R 10 , CONR 9 R 10 , unsubstituted or phenyl substituted with 1-4 independently selected from the following groups, the following groups are : Halogen, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxy Carbonyl, C 1 -C 6 alkylthio or C 1 -C 6 alkylsulfonyl;R 5、R 6可与相邻的C连接形成三元环、四元环、五元环或者六元环； R 5 and R 6 may be connected with adjacent C to form a three-membered ring, a four-membered ring, a five-membered ring or a six-membered ring;R 3、R 5可与相邻的C连接形成五元环或者六元环； R 3 and R 5 may be connected with adjacent C to form a five-membered ring or a six-membered ring;R 7选自氢、C 1-C 6烷基、C 1-C 6卤代烷基、C 3-C 6环烷基、C 3-C 6烯基、C 3-C 6炔基、C 1-C 6烷氧基C 1-C 6烷基、C 1-C 6烷羰基氧基C 2-C 4烷基、C 2-C 6烯羰基氧基C 2-C 4烷基、二(C 1-C 6烷基)氨基C 2-C 4烷基、(C 1-C 6烷基)氨基C 2-C 4烷基，未取代或者被1-4个独立选自以下基团取代的苯基、苄基、呋喃亚甲基、噻唑亚甲基、四氢呋喃亚甲基或吡啶亚甲基，以下基团为：卤素、CN、NO 2、C 1-C 6烷基、C 1-C 6卤代烷基、C 1-C 6烷氧基、C 1-C 6卤代烷氧基、C 1-C 6烷氧基羰基、C 1-C 6烷硫基或C 1-C 6烷基磺酰基； R 7 is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1- C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy C 2 -C 4 alkyl, C 2 -C 6 alkenyl carbonyloxy C 2 -C 4 alkyl, two (C 1- C 6 alkyl) amino C 2 -C 4 alkyl, (C 1 -C 6 alkyl) amino C 2 -C 4 alkyl, unsubstituted or substituted with 1-4 independently selected from the following groups Phenyl, benzyl, furimethylene, thiazolymethylene, tetrahydrofurimethylene or pyridine methylene, the following groups are: halogen, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio or C 1 -C 6 alkylsulfonyl ；R 8选自氢、C 1-C 6烷基、C 1-C 6卤代烷基、C 1-C 6烷氧基羰基、C 1-C 6烷基羰基、C 1-C 6卤代烷基羰基、C 3-C 6环烷基羰基、C 3-C 6卤代环烷基羰基、C 1-C 6烷基磺酰基、C 1-C 6卤代烷基磺酰基、C 1-C 6烷基氨基磺酰基、二(C 1-C 6)烷基氨基磺酰基、C 1-C 6烷基氨基羰基、二(C 1-C 6)烷基氨基羰基、二(C 1-C 6)烷基氨基硫代羰基、C 1-C 6烷硫基C 2-C 6烷基羰基，未取代或者被1-4个独立选自以下基团取代的苯基、苯基C 1-C 2烷基、苯基C 2-C 4烯基、苯基羰基、苯基C 1-C 2烷基羰基、苯氧基C 1-C 2烷基羰基、苯基C 2-C 4烯基羰基、杂芳基、杂芳基C 1-C 2烷基、杂芳基羰基，以下基团为：卤素、CN、NO 2、C 1-C 6烷基、C 1-C 6卤代烷基、C 1-C 6烷氧基、C 1-C 6卤代烷氧基、C 1-C 6烷氧基羰基、C 1-C 6烷硫基、C 1-C 6烷基磺酰基或被1-4个独立所述基团取代的苯氧基：所述基团为卤素、CN、NO 2、C 1-C 6烷基、C 1-C 6卤代烷基、C 1-C 6烷氧基或C 1-C 6卤代烷氧基； R 8 is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 3 -C 6 halocycloalkylcarbonyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 alkylamino Sulfonyl, di(C 1 -C 6 )alkylaminosulfonyl, C 1 -C 6 alkylaminocarbonyl, di(C 1 -C 6 )alkylaminocarbonyl, di(C 1 -C 6 )alkyl Aminothiocarbonyl, C 1 -C 6 alkylthio, C 2 -C 6 alkylcarbonyl, unsubstituted or substituted by 1-4 independently selected from the following phenyl groups, phenyl C 1 -C 2 alkyl groups , Phenyl C 2 -C 4 alkenyl, phenyl carbonyl, phenyl C 1 -C 2 alkylcarbonyl, phenoxy C 1 -C 2 alkylcarbonyl, phenyl C 2 -C 4 alkenyl carbonyl, hetero Aryl, heteroaryl C 1 -C 2 alkyl, heteroaryl carbonyl, the following groups are: halogen, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1- C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl or independently by 1-4 Phenoxy substituted by the group: the group is halogen, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1- C 6 haloalkoxy;R 9、R 10分别选自氢、C 1-C 6烷基、C 1-C 6卤代烷基、C 1-C 6烷氧基羰基C 1-C 6烷基、SO 2NH(C 1-C 6烷基)或SO 2N(C 1-C 6烷基)(C 1-C 6烷基)； R 9 and R 10 are respectively selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, SO 2 NH (C 1- C 6 alkyl) or SO 2 N (C 1 -C 6 alkyl) (C 1 -C 6 alkyl);Q选自如下Q1-Q13中任意一个；Q is selected from any of the following Q1-Q13;
R 11选自C 1-C 6烷基或C 1-C 6卤代烷基； R 11 is selected from C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;R 12选自C 1-C 6烷基、C 1-C 6卤代烷基、C 1-C 6烷氧基或C 1-C 6卤代烷氧基； R 12 is selected from C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy;R 13选自氢、卤素、CN、NO 2或C 1-C 6烷基； R 13 is selected from hydrogen, halogen, CN, NO 2 or C 1 -C 6 alkyl;R 14选自C 1-C 6烷基或C 1-C 6卤代烷基； R 14 is selected from C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;R 15选自C 1-C 6烷基、C 3-C 6环烷基或C 1-C 6卤代烷基； R 15 is selected from C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl or C 1 -C 6 haloalkyl;或，式(I)化合物的可农用盐或衍生物。Or, an agriculturally acceptable salt or derivative of the compound of formula (I). - 按照权利要求1所述的化合物，其特征在于：通式(I)中The compound according to claim 1, wherein: in the general formula (I)R 1、R 2分别选自氢、卤素或C 1-C 4烷基； R 1 and R 2 are each selected from hydrogen, halogen or C 1 -C 4 alkyl;R 3选自氢、氰基、C 1-C 4烷基、苯基或被1-4个独立选自以下基团取代的苯基：卤素、CN、NO 2、C 1-C 4烷基、C 1-C 4卤代烷基、C 1-C 4烷氧基、C 1-C 4卤代烷氧基或C 1-C 4烷氧基羰基； R 3 is selected from hydrogen, cyano, C 1 -C 4 alkyl, phenyl, or phenyl substituted with 1-4 independently selected from the following groups: halogen, CN, NO 2 , C 1 -C 4 alkyl , C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkoxycarbonyl;R 4选自氢、氰基、C 1-C 4烷基、CO 2R 7或CH 2OR 8； R 4 is selected from hydrogen, cyano, C 1 -C 4 alkyl, CO 2 R 7 or CH 2 OR 8 ;R 5选自氢、氰基、C 1-C 4烷基、C 1-C 4烷氧基、C 1-C 4卤代烷基、C 1-C 4烷基CO 2R 7、CO 2R 7、CH 2Si[三(C 1-C 6烷基)]、未取代或被1-4个独立选自以下基团取代的苯基：卤素、CN、NO 2、C 1-C 4烷基、C 1-C 4卤代烷基、C 1-C 4烷氧基或C 1-C 4卤代烷氧基； R 5 is selected from hydrogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 alkyl CO 2 R 7 , CO 2 R 7 , CH 2 Si [tris (C 1 -C 6 alkyl)], unsubstituted or phenyl substituted with 1-4 independently selected from the following groups: halogen, CN, NO 2 , C 1 -C 4 alkyl , C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;R 6选自氢、氰基、C 1-C 6烷基、C 1-C 6烷氧基、C 1-C 6卤代烷基、C 3-C 6环烷基、C 1-C 6烷基CO 2R 7、CO 2R 7、CH 2OR 8、CH 2NR 9R 10、CONR 9R 10、未取代或被1-4个独立选自以下基团取代的苯基：卤素、CN、NO 2、C 1-C 4烷基、C 1-C 4卤代烷基、C 1-C 4烷氧基或C 1-C 4卤代烷氧基； R 6 is selected from hydrogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkyl CO 2 R 7 , CO 2 R 7 , CH 2 OR 8 , CH 2 NR 9 R 10 , CONR 9 R 10 , unsubstituted or phenyl substituted with 1-4 independently selected from the following groups: halogen, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;R 5、R 6可与相邻的C连接形成四元环或五元环； R 5 and R 6 may be connected with adjacent C to form a four-membered ring or a five-membered ring;R 3、R 5可与相邻的C连接形成五元环或六元环； R 3 and R 5 may be connected with adjacent C to form a five-membered ring or a six-membered ring;R 7选自氢、C 1-C 4烷基、C 1-C 4卤代烷基、C 3-C 6环烷基、C 3-C 6烯基、C 3-C 6炔基、C 1-C 6烷氧基C 1-C 6烷基、C 1-C 6烷羰基氧基C 2-C 4烷基、C 2-C 6烯羰基氧基C 2-C 4烷基、二(C 1-C 6烷基)氨基C 2-C 4烷基、(C 1-C 6烷基)氨基C 2-C 4烷基，未取代或者被1-4个独立选自以下基团取代的苯基、苄基、呋喃亚甲基、噻唑亚甲基、四氢呋喃亚甲基或吡啶亚甲基，以下基团为：卤素、CN、NO 2、C 1-C 4烷基、C 1-C 8卤代烷基、C 1-C 4烷氧基、C 1-C 4卤代烷氧基或C 1-C 4烷氧基羰基； R 7 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1- C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy C 2 -C 4 alkyl, C 2 -C 6 alkenyl carbonyloxy C 2 -C 4 alkyl, two (C 1- C 6 alkyl) amino C 2 -C 4 alkyl, (C 1 -C 6 alkyl) amino C 2 -C 4 alkyl, unsubstituted or substituted with 1-4 independently selected from the following groups Phenyl, benzyl, furylidene, thiazolyl, tetrahydrofurylidene or pyridinemethylene, the following groups are: halogen, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 8 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkoxycarbonyl group;R 8选自氢、C 1-C 4烷基、C 1-C 4卤代烷基、C 1-C 4烷氧基羰基、C 1-C 4烷基羰基、C 1-C 6卤代烷基羰基、C 3-C 6环烷基羰基、C 3-C 6卤代环烷基羰基、C 1-C 4烷基磺酰基、C 1-C 4卤代烷基磺酰基、C 1-C 4烷基氨基磺酰基、二(C 1-C 4)烷基氨基磺酰基、C 1-C 4烷基氨基羰基、二(C 1-C 4)烷基氨基羰基、二(C 1-C 4)烷基氨基硫代羰基、C 1-C 4烷硫基C 2-C 4烷基羰基，未取代或者被1-4个独立选自以下基团取代的苯基、苯基C 1-C 2烷基、苯基C 2-C 4烯基、苯基羰基、苯基C 1-C 2烷基羰基、苯氧基C 1-C 2烷基羰基、苯基C 2-C 4烯基羰基、杂芳基、杂芳基C 1-C 2烷基、杂芳 基羰基，以下基团为：卤素、CN、NO 2、C 1-C 4烷基、C 1-C 4卤代烷基、C 1-C 4烷氧基、C 1-C 4卤代烷氧基、C 1-C 4烷氧基羰基、C 1-C 4烷硫基、C 1-C 4烷基磺酰基或被1-4个独立的所述基团取代的苯氧基：所述基团为卤素、CN、NO 2、C 1-C 4烷基、C 1-C 4卤代烷基、C 1-C 4烷氧基或C 1-C 4卤代烷氧基； R 8 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 3 -C 6 halocycloalkylcarbonyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkylamino Sulfonyl, di(C 1 -C 4 )alkylaminosulfonyl, C 1 -C 4 alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkyl Aminothiocarbonyl, C 1 -C 4 alkylthio, C 2 -C 4 alkylcarbonyl, unsubstituted or substituted by 1-4 independently selected from the following phenyl groups, phenyl C 1 -C 2 alkyl groups , Phenyl C 2 -C 4 alkenyl, phenyl carbonyl, phenyl C 1 -C 2 alkylcarbonyl, phenoxy C 1 -C 2 alkylcarbonyl, phenyl C 2 -C 4 alkenyl carbonyl, hetero Aryl, heteroaryl C 1 -C 2 alkyl, heteroaryl carbonyl, the following groups are: halogen, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1- C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfonyl or independently by 1-4 The group substituted phenoxy group: the group is halogen, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;R 9、R 10分别选自氢、C 1-C 4烷基、C 1-C 4卤代烷基、C 1-C 4烷氧基羰基C 1-C 4烷基、SO 2NH(C 1-C 4烷基)或SO 2N(C 1-C 4烷基)(C 1-C 4烷基)； R 9 and R 10 are respectively selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxycarbonyl C 1 -C 4 alkyl, SO 2 NH (C 1- C 4 alkyl) or SO 2 N (C 1 -C 4 alkyl) (C 1 -C 4 alkyl);Q选自如下Q1-Q13中任意一个；Q is selected from any of the following Q1-Q13;R 11选自C 1-C 4烷基或C 1-C 4卤代烷基； R 11 is selected from C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;R 12选自C 1-C 4烷基、C 1-C 4卤代烷基、C 1-C 4烷氧基或C 1-C 4卤代烷氧基； R 12 is selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;R 13选自氢、卤素、CN、NO 2或C 1-C 4烷基； R 13 is selected from hydrogen, halogen, CN, NO 2 or C 1 -C 4 alkyl;R 14选自C 1-C 4烷基或C 1-C 4卤代烷基； R 14 is selected from C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;R 15选自C 1-C 4烷基、C 3-C 6环烷基或C 1-C 4卤代烷基； R 15 is selected from C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl or C 1 -C 4 haloalkyl;或，式(I)化合物的可农用盐或衍生物。Or, an agriculturally acceptable salt or derivative of the compound of formula (I).
- 按照权利要求2所述的化合物，其特征在于：通式(I)中The compound according to claim 2, characterized in that: in the general formula (I)R 1、R 2分别选自氢、卤素、甲基、乙基、丙基或异丙基； R 1 and R 2 are respectively selected from hydrogen, halogen, methyl, ethyl, propyl or isopropyl;R 3选自氢、氰基、C 1-C 4烷基、苯基或被1-2个独立选自以下基团取代的苯基：氟、氯、溴、CN、NO 2、甲基、乙基、异丙基、叔丁基、三氟甲基、二氟甲基、甲氧基、乙氧基、叔丁氧基、二氟甲氧基、三氟甲氧基、三氟乙氧基或二氟乙氧基； R 3 is selected from hydrogen, cyano, C 1 -C 4 alkyl, phenyl or phenyl substituted with 1-2 independently selected from the following groups: fluorine, chlorine, bromine, CN, NO 2 , methyl, Ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, tert-butoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy Radical or difluoroethoxy;R 4选自氢、氰基或C 1-C 4烷基； R 4 is selected from hydrogen, cyano or C 1 -C 4 alkyl;R 5选自氢、氰基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、三氟甲基、二氟甲基、三氟乙基、CH 2CO 2R 7、CO 2R 7、CH 2SiC(CH 3) 3、未取代或被1-2个独立选自以下基团取代的苯基，以下基团为：氟、氯、溴、CN、NO 2、甲基、乙基、异丙基、叔丁基、三氟甲基、二氟甲基、甲氧基、乙氧基、叔丁氧基、二氟甲氧基、三氟甲氧基、三氟乙氧基或二氟乙氧基； R 5 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, trifluoroethyl, CH 2 CO 2 R 7 , CO 2 R 7 , CH 2 SiC(CH 3 ) 3 , unsubstituted or phenyl substituted with 1-2 independently selected from the following groups, the following groups are: fluorine, chlorine, bromine , CN, NO 2 , methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, tert-butoxy, difluoromethoxy, three Fluoromethoxy, trifluoroethoxy or difluoroethoxy;R 6选自氢、氰基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、甲氧基、乙氧基、异丙氧基、叔丁氧基、环丙基、环戊基、环己基、CH 2CO 2R 7、CH 2CH 2CO 2R 7、CO 2R 7、CH 2OR 8、CH 2NR 9R 10、CONR 9R 10、未取代或被1-2个独立选自以下基团取代的苯基，以下基团为：氟、氯、溴、CN、NO 2、甲基、乙基、异丙基、叔丁基、三氟甲基、二氟甲基、甲氧基、乙氧基、叔丁氧基、二氟甲氧基、三氟甲氧基、三氟乙氧基或二氟乙氧基； R 6 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butyl Oxy, cyclopropyl, cyclopentyl, cyclohexyl, CH 2 CO 2 R 7 , CH 2 CH 2 CO 2 R 7 , CO 2 R 7 , CH 2 OR 8 , CH 2 NR 9 R 10 , CONR 9 R 10. Unsubstituted or substituted by 1-2 groups independently selected from the following groups, the following groups are: fluorine, chlorine, bromine, CN, NO 2 , methyl, ethyl, isopropyl, tert-butyl , Trifluoromethyl, difluoromethyl, methoxy, ethoxy, tert-butoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy or difluoroethoxy;R 5、R 6可与相邻的C连接形成四元环或五元环； R 5 and R 6 may be connected with adjacent C to form a four-membered ring or a five-membered ring;R 3、R 5可与相邻的C连接形成五元环或六元环； R 3 and R 5 may be connected with adjacent C to form a five-membered ring or a six-membered ring;R 7选自氢、C 1-C 4烷基、C 1-C 4卤代烷基、C 3-C 6环烷基、C 3-C 6烯基、C 3-C 6炔基、C 1-C 6烷氧基C 1-C 6烷基、C 1-C 6烷羰基氧基C 2-C 4烷基、C 2-C 6烯羰基氧基C 2-C 4烷基、二(C 1-C 6烷基)氨基C 2-C 4烷基、(C 1-C 6烷基)氨基C 2-C 4烷基，未取代或者被1-4个独立选自以下基团取代的苯基、苄基、呋喃亚甲基或四氢呋喃亚甲基：氟、氯、溴、CN、NO 2、甲基、乙基、异丙基、叔丁基、三氟甲基、甲氧基、乙氧基、叔丁氧基、二氟甲氧基、三氟甲氧基、三氟乙氧基或二氟乙氧基； R 7 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1- C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy C 2 -C 4 alkyl, C 2 -C 6 alkenyl carbonyloxy C 2 -C 4 alkyl, two (C 1- C 6 alkyl) amino C 2 -C 4 alkyl, (C 1 -C 6 alkyl) amino C 2 -C 4 alkyl, unsubstituted or substituted with 1-4 independently selected from the following groups Phenyl, benzyl, furanmethylene or tetrahydrofuranmethylene: fluorine, chlorine, bromine, CN, NO 2 , methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, methoxy, Ethoxy, tert-butoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy or difluoroethoxy;R 8选自氢、C 1-C 4烷基、C 1-C 4卤代烷基、C 1-C 4烷氧基羰基、C 1-C 4烷基羰基、C 1-C 4卤代烷基羰基、C 3-C 6环烷基羰基、C 3-C 6卤代环烷基羰基、C 1-C 4烷基磺酰基、C 1-C 4卤代烷基磺酰基、C 1-C 3烷基氨基磺酰基、二(C 1-C 3)烷基氨基磺酰基、C 1-C 3烷基氨基羰基、二(C 1-C 3)烷基氨基羰基、二(C 1-C 3)烷基氨基硫代羰基、C 1-C 2烷硫基C 2-C 4烷基羰基，未取代或者被1-4个独立选自以下基团取代的苯基C 1-C 2烷基、苯基羰基、苯基C 1-C 2烷基羰基、苯基C 2-C 4烯基羰基、苯氧基C 1-C 2烷基羰基、噻吩羰基、吡唑羰基、喹啉羰基，以下基团为：卤素、CN、NO 2、C 1-C 4烷基、C 1-C 4卤代烷基、C 1-C 4烷氧基、C 1-C 4卤代烷氧基、C 1-C 4烷氧基羰基、C 1-C 4烷硫基、C 1-C 4烷基磺酰基或被1-4个独立所述基团取代的苯氧基：所述基团为卤素、CN、 NO 2、C 1-C 4烷基、C 1-C 4卤代烷基、C 1-C 4烷氧基或C 1-C 4卤代烷氧基； R 8 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 3 -C 6 halocycloalkylcarbonyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 3 alkylamino Sulfonyl, di(C 1 -C 3 )alkylaminosulfonyl, C 1 -C 3 alkylaminocarbonyl, di(C 1 -C 3 )alkylaminocarbonyl, di(C 1 -C 3 )alkyl Aminothiocarbonyl, C 1 -C 2 alkylthio C 2 -C 4 alkylcarbonyl, unsubstituted or phenyl substituted with 1-4 independently selected from the following groups: C 1 -C 2 alkyl, phenyl Carbonyl, phenyl C 1 -C 2 alkylcarbonyl, phenyl C 2 -C 4 alkenyl carbonyl, phenoxy C 1 -C 2 alkylcarbonyl, thiophene carbonyl, pyrazole carbonyl, quinoline carbonyl, the following groups It is: halogen, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy Carbonyl group, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfonyl or phenoxy substituted by 1-4 independent groups: the groups are halogen, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;R 9、R 10分别选自氢、C 1-C 4烷基、C 1-C 4卤代烷基、C 1-C 4烷氧基羰基C 1-C 4烷基、SO 2NH(C 1-C 4烷基)或SO 2N(C 1-C 4烷基)(C 1-C 4烷基)； R 9 and R 10 are respectively selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxycarbonyl C 1 -C 4 alkyl, SO 2 NH (C 1- C 4 alkyl) or SO 2 N (C 1 -C 4 alkyl) (C 1 -C 4 alkyl);Q选自如下Q1-Q13中任意一个；Q is selected from any of the following Q1-Q13;R 11选自C 1-C 4烷基或C 1-C 2卤代烷基； R 11 is selected from C 1 -C 4 alkyl or C 1 -C 2 haloalkyl;R 12选自C 1-C 4烷基、C 1-C 4卤代烷基、C 1-C 4烷氧基或C 1-C 4卤代烷氧基； R 12 is selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;R 13选自氢、卤素或C 1-C 4烷基； R 13 is selected from hydrogen, halogen or C 1 -C 4 alkyl;R 14选自C 1-C 4烷基或C 1-C 2卤代烷基； R 14 is selected from C 1 -C 4 alkyl or C 1 -C 2 haloalkyl;R 15选自C 1-C 4烷基、C 3-C 6环烷基或C 1-C 2卤代烷基； R 15 is selected from C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl or C 1 -C 2 haloalkyl;或，式(I)化合物的可农用盐或衍生物。Or, an agriculturally acceptable salt or derivative of the compound of formula (I).
- 按照权利要求3所述的化合物，其特征在于：通式(I)中The compound according to claim 3, characterized in that: in the general formula (I)R 1、R 2分别选自氢、氟、氯、溴或甲基； R 1 and R 2 are respectively selected from hydrogen, fluorine, chlorine, bromine or methyl;R 3选自氢、氰基、C 1-C 4烷基、苯基或被1-2个独立选自以下基团取代的苯基：氟、氯、溴或甲基； R 3 is selected from hydrogen, cyano, C 1 -C 4 alkyl, phenyl or phenyl substituted with 1-2 groups independently selected from the following: fluorine, chlorine, bromine or methyl;R 4选自氢、氰基、甲基、乙基、正丙基、异丙基或叔丁基； R 4 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl or tert-butyl;R 5选自氢、氰基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、三氟甲基、二氟甲基、三氟乙基、CH 2CO 2R 7、CO 2R 7、CH 2SiC(CH 3) 3、未取代或被1-2个独立选自以下基团取代的苯基：氟、氯、溴、CN、NO 2、甲基、异丙基、三氟甲基、甲氧基、二氟甲氧基或三氟甲氧基； R 5 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, trifluoroethyl, CH 2 CO 2 R 7 , CO 2 R 7 , CH 2 SiC(CH 3 ) 3 , unsubstituted or phenyl substituted with 1-2 independently selected from the following groups: fluorine, chlorine, bromine, CN, NO 2 , Methyl, isopropyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy;R 6选自氢、氰基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、甲氧基、乙氧基、异丙氧基、叔丁氧基、环丙基、环戊基、环己基、CH 2CO 2R 7、CH 2CH 2CO 2R 7、CO 2R 7、CH 2OR 8、CONR 9R 10、未取代或被1-2个独立选自以下基团取代的苯基：氟、氯、溴、CN、NO 2、甲基、异丙基、三氟甲基、甲氧基、二氟甲氧基或三氟甲氧基； R 6 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butyl Oxy, cyclopropyl, cyclopentyl, cyclohexyl, CH 2 CO 2 R 7 , CH 2 CH 2 CO 2 R 7 , CO 2 R 7 , CH 2 OR 8 , CONR 9 R 10 , unsubstituted or 1 -2 phenyl substituted independently selected from the following groups: fluorine, chlorine, bromine, CN, NO 2 , methyl, isopropyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethyl Oxy;R 5、R 6可与相邻的C连接形成四氢呋喃酮环； R 5 and R 6 can be connected with adjacent C to form a tetrahydrofuranone ring;R 3、R 5可与相邻的C连接形成环戊烷或环己烷； R 3 and R 5 can be connected with adjacent C to form cyclopentane or cyclohexane;R 7选自氢、C 1-C 4烷基、C 1-C 4卤代烷基、C 3-C 6环烷基、烯丙基、炔丙基、C 1-C 3烷氧基C 1-C 3烷基、C 1-C 4烷羰基氧基C 2-C 3烷基，C 2-C 4烯羰基氧基C 2-C 3烷基、二(C 1-C 3烷基)氨基C 2-C 3烷基、(C 1-C 3烷基)氨基C 2-C 3烷基、未取代或者被1-4个独立选自以下基团取代的苯基、苄基、呋喃亚甲基或四氢呋喃亚甲基：氟、氯、溴、CN、NO 2、甲基、乙基、异丙基或叔丁基； R 7 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, allyl, propargyl, C 1 -C 3 alkoxy C 1- C 3 alkyl, C 1 -C 4 alkylcarbonyloxy C 2 -C 3 alkyl, C 2 -C 4 alkenyl carbonyloxy C 2 -C 3 alkyl, di(C 1 -C 3 alkyl)amino C 2 -C 3 alkyl, (C 1 -C 3 alkyl) amino C 2 -C 3 alkyl, unsubstituted or substituted by 1-4 independently selected from the following groups of phenyl, benzyl, furanolide Methyl or tetrahydrofuran methylene: fluorine, chlorine, bromine, CN, NO 2 , methyl, ethyl, isopropyl or tert-butyl;R 8选自氢、C 1-C 4烷基、C 1-C 4卤代烷基、C 1-C 4烷氧基羰基、C 1-C 4烷基羰基、C 1-C 4卤代烷基羰基、C 3-C 6环烷基羰基、C 1-C 4烷基磺酰基、C 1-C 4卤代烷基磺酰基、二(C 1-C 3)烷基氨基磺酰基、C 1-C 3烷基氨基羰基、二(C 1-C 3)烷基氨基羰基、C 1-C 2烷硫基C 2-C 4烷基羰基，未取代或者被1-3个独立选自以下基团的苯基羰基、苯乙酰基、苯丙酰基、苯氧基C 1-C 2烷基羰基或喹啉羰基：氟、氯、溴、CN、NO 2、C 1-C 4烷基、C 1-C 4卤代烷基、C 1-C 4烷氧基、C 1-C 4卤代烷氧基、C 1-C 4烷硫基或C 1-C 4烷基磺酰基； R 8 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, di(C 1 -C 3 )alkylaminosulfonyl, C 1 -C 3 alkane Alkylaminocarbonyl, di(C 1 -C 3 )alkylaminocarbonyl, C 1 -C 2 alkylthio C 2 -C 4 alkylcarbonyl, unsubstituted or benzene with 1-3 independently selected from the following groups Carbonyl, phenylacetyl, phenylpropionyl, phenoxy C 1 -C 2 alkyl carbonyl or quinoline carbonyl: fluorine, chlorine, bromine, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio or C 1 -C 4 alkylsulfonyl;R 9、R 10分别选自氢、C 1-C 4烷基、C 1-C 4卤代烷基、C 1-C 3烷氧基羰基C 1-C 2烷基、SO 2NH(C 1-C 4烷基)或SO 2N(C 1-C 2烷基)(C 1-C 4烷基)； R 9 and R 10 are respectively selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 3 alkoxycarbonyl C 1 -C 2 alkyl, SO 2 NH (C 1- C 4 alkyl) or SO 2 N (C 1 -C 2 alkyl) (C 1 -C 4 alkyl);Q选自如下Q1-Q13中任意一个；Q is selected from any of the following Q1-Q13;R 11选自甲基、乙基、正丙基、异丙基、异丁基、叔丁基、二氟甲基、三氟乙基或二氟乙基； R 11 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, difluoromethyl, trifluoroethyl or difluoroethyl;R 12选自甲基、乙基、正丙基、异丙基、异丁基、叔丁基、三氟甲基、二氟甲基、甲氧基、乙氧基、异丙氧基、叔丁氧基、三氟甲氧基、二氟甲氧基、三氟乙氧基或者二氟乙氧基； R 12 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, isopropoxy, tert Butoxy, trifluoromethoxy, difluoromethoxy, trifluoroethoxy or difluoroethoxy;R 13选自氢、氟、氯、溴、甲基或乙基； R 13 is selected from hydrogen, fluorine, chlorine, bromine, methyl or ethyl;R 14选自甲基、乙基、正丙基、异丙基、异丁基、叔丁基、二氟甲基、三氟乙基或二氟乙 基； R 14 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, difluoromethyl, trifluoroethyl or difluoroethyl;R 15选自甲基、乙基、正丙基、异丙基、异丁基、叔丁基、环丙基、二氟甲基、三氟甲基、三氟乙基或二氟乙基； R 15 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, cyclopropyl, difluoromethyl, trifluoromethyl, trifluoroethyl or difluoroethyl;或，式(I)化合物的可农用盐或衍生物。Or, an agriculturally acceptable salt or derivative of the compound of formula (I).
- 按照权利要求4所述的化合物，其特征在于：通式(I)中The compound according to claim 4, wherein: in the general formula (I)R 1、R 2分别选自氢、氟、氯或溴； R 1 and R 2 are respectively selected from hydrogen, fluorine, chlorine or bromine;R 3选自氢或C 1-C 4烷基； R 3 is selected from hydrogen or C 1 -C 4 alkyl;R 4选自氢、甲基、乙基、正丙基、异丙基或叔丁基； R 4 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl or tert-butyl;R 5选自氢、氰基、甲基、乙基、正丙基、异丙基、异丁基、叔丁基、三氟甲基、CH 2CO 2CH 3、CH 2CO 2C 2H 5、CO 2CH 3、CO 2C 2H 5、CH 2SiC(CH 3) 3、未取代或被1-2个独立选自以下基团取代的苯基：氟、氯或溴； R 5 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, trifluoromethyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5. CO 2 CH 3 , CO 2 C 2 H 5 , CH 2 SiC(CH 3 ) 3 , unsubstituted or phenyl substituted with 1-2 independently selected from the following groups: fluorine, chlorine or bromine;R 6选自氢、氰基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、甲氧基、乙氧基、异丙氧基、叔丁氧基、环丙基、环戊基、环己基、CH 2CO 2CH 3、CH 2CO 2C 2H 5、CH 2CH 2CO 2CH 3、CH 2CH 2CO 2C 2H 5、CO 2R 7、CH 2OR 8、CONR 9R 10、未取代或被1-2个独立选自以下基团取代的苯基：氟、氯或溴； R 6 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butyl Oxy, cyclopropyl, cyclopentyl, cyclohexyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5 , CH 2 CH 2 CO 2 CH 3 , CH 2 CH 2 CO 2 C 2 H 5 , CO 2 R 7 , CH 2 OR 8 , CONR 9 R 10 , unsubstituted or phenyl substituted with 1-2 independently selected from the following groups: fluorine, chlorine or bromine;R 5、R 6可与相邻的C连接形成四氢呋喃酮环； R 5 and R 6 can be connected with adjacent C to form a tetrahydrofuranone ring;R 3、R 5可与相邻的C连接形成环戊烷或环己烷； R 3 and R 5 can be connected with adjacent C to form cyclopentane or cyclohexane;R 7选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、三氟乙基、二氟乙基、1-氯乙基、1-氟乙基、环丙基、环戊基、环己基、烯丙基、炔丙基、甲氧基乙基、乙氧基乙基、乙酰氧基乙基、丙烯酰氧基乙基、甲基丙烯酰氧基、二甲氨基乙基、二乙氨基乙基、二异丙基氨基乙基、甲氨基乙基、乙氨基乙基、异丙氨基乙基、叔丁氨基乙基、四氢呋喃亚甲基、未取代或被1-2个独立选自以下基团取代的苯基：氟、氯或溴； R 7 is selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, trifluoroethyl, difluoroethyl, 1-chloroethyl, 1- Fluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl, allyl, propargyl, methoxyethyl, ethoxyethyl, acetoxyethyl, acryloxyethyl, methyl Acryloyloxy, dimethylaminoethyl, diethylaminoethyl, diisopropylaminoethyl, methylaminoethyl, ethylaminoethyl, isopropylaminoethyl, tert-butylaminoethyl, methylene tetrahydrofuran Group, unsubstituted or phenyl substituted with 1-2 groups independently selected from the group consisting of fluorine, chlorine or bromine;R 8选自氢、C 1-C 4烷氧基羰基、C 1-C 4烷基羰基、C 1-C 4卤代烷基羰基、C 3-C 6环烷基羰基、C 1-C 4烷基磺酰基、C 1-C 4卤代烷基磺酰基、二(C 1-C 2)烷基氨基磺酰基、C 1-C 2烷基氨基羰基、二(C 1-C 3)烷基氨基羰基、C 1-C 2烷硫基C 2-C 4烷基羰基，未取代或者被1-3个独立选自以下基团的苯基羰基、苯乙酰基、苯丙酰基、苯氧基C 1-C 2烷基羰基或喹啉羰基：氟、氯、溴、CN、NO 2、C 1-C 4烷基、C 1-C 4卤代烷基、C 1-C 4烷氧基、C 1-C 4卤代烷氧基、或C 1-C 4烷基磺酰基； R 8 is selected from hydrogen, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 1 -C 4 alkane Alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, di(C 1 -C 2 )alkylaminosulfonyl, C 1 -C 2 alkylaminocarbonyl, di(C 1 -C 3 )alkylaminocarbonyl , C 1 -C 2 alkylthio C 2 -C 4 alkylcarbonyl, unsubstituted or by 1-3 independently selected from the following groups phenylcarbonyl, phenylacetyl, phenylpropionyl, phenoxy C 1 -C 2 alkyl carbonyl or quinoline carbonyl: fluorine, chlorine, bromine, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1- C 4 haloalkoxy, or C 1 -C 4 alkylsulfonyl;R 9选自氢、C 1-C 4烷基或C 1-C 4卤代烷基； R 9 is selected from hydrogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;R 10选自氢、C 1-C 4烷基、C 1-C 3烷氧基羰基C 1-C 2烷基、SO 2NH(C 1-C 4烷基)或SO 2N(C 1-C 2烷基)(C 1-C 4烷基)； R 10 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 3 alkoxycarbonyl C 1 -C 2 alkyl, SO 2 NH (C 1 -C 4 alkyl) or SO 2 N (C 1 -C 2 alkyl) (C 1 -C 4 alkyl);Q选自如下Q1、Q2、Q3、Q4、Q5、Q6、Q7、Q8或Q13；Q is selected from the following Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8 or Q13;R 11选自甲基、乙基、异丙基、叔丁基、二氟甲基、三氟乙基或二氟乙基； R 11 is selected from methyl, ethyl, isopropyl, tert-butyl, difluoromethyl, trifluoroethyl or difluoroethyl;R 12选自甲基、三氟甲基、二氟甲基、甲氧基、异丙氧基、三氟甲氧基、二氟甲氧基、三氟乙氧基或者二氟乙氧基； R 12 is selected from methyl, trifluoromethyl, difluoromethyl, methoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, trifluoroethoxy or difluoroethoxy;R 13选自氢、氟、氯、溴或甲基； R 13 is selected from hydrogen, fluorine, chlorine, bromine or methyl;R 14选自甲基、乙基、正丙基、异丙基、异丁基或叔丁基； R 14 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl or tert-butyl;R 15选自甲基、环丙基或三氟甲基； R 15 is selected from methyl, cyclopropyl or trifluoromethyl;或，具有羧基的式(I)化合物的可农用盐或衍生物。Or, an agriculturally acceptable salt or derivative of a compound of formula (I) having a carboxyl group.
- 按照权利要求5所述的化合物，其特征在于：通式(I)中The compound according to claim 5, wherein: in the general formula (I)R 1、R 2分别选自氢、氟或氯； R 1 and R 2 are each selected from hydrogen, fluorine or chlorine;R 3选自氢或C 1-C 4烷基； R 3 is selected from hydrogen or C 1 -C 4 alkyl;R 4选自氢、甲基、乙基、正丙基、异丙基或叔丁基； R 4 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl or tert-butyl;R 5选自氢、甲基、乙基、三氟甲基、CH 2CO 2CH 3、CH 2CO 2C 2H 5、CO 2CH 3、CO 2C 2H 5、CH 2SiC(CH 3) 3、未取代或被1-2个独立选自以下基团取代的苯基：氟、氯或溴； R 5 is selected from hydrogen, methyl, ethyl, trifluoromethyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5 , CO 2 CH 3 , CO 2 C 2 H 5 , CH 2 SiC (CH 3 ) 3. Unsubstituted or substituted phenyl groups independently selected from the following groups: fluorine, chlorine or bromine;R 6选自氢、氰基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、甲氧基、 乙氧基、异丙氧基、叔丁氧基、环丙基、环戊基、环己基、CH 2CO 2CH 3、CH 2CO 2C 2H 5、CH 2CH 2CO 2CH 3、CH 2CH 2CO 2C 2H 5、CO 2R 7、CH 2OR 8、CONR 9R 10、未取代或被1-2个独立选自以下基团取代的苯基：氟、氯或溴； R 6 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, isopropoxy, tert-butyl Oxy, cyclopropyl, cyclopentyl, cyclohexyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5 , CH 2 CH 2 CO 2 CH 3 , CH 2 CH 2 CO 2 C 2 H 5 , CO 2 R 7 , CH 2 OR 8 , CONR 9 R 10 , unsubstituted or phenyl substituted with 1-2 independently selected from the following groups: fluorine, chlorine or bromine;R 5、R 6可与相邻的C连接形成四氢呋喃酮环； R 5 and R 6 can be connected with adjacent C to form a tetrahydrofuranone ring;R 3、R 5可与相邻的C连接形成环戊烷或环己烷； R 3 and R 5 can be connected with adjacent C to form cyclopentane or cyclohexane;R 7选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、三氟乙基、二氟乙基、1-氯乙基、1-氟乙基、环丙基、环己基、烯丙基、炔丙基、甲氧基乙基、乙氧基乙基、乙酰氧基乙基、丙烯酰氧基乙基、甲基丙烯酰氧基、二甲氨基乙基、二异丙基氨基乙基、甲氨基乙基、乙氨基乙基、异丙氨基乙基、叔丁氨基乙基、四氢呋喃亚甲基、未取代或被1-2个独立选自以下基团取代的苯基：氟、氯或溴； R 7 is selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, trifluoroethyl, difluoroethyl, 1-chloroethyl, 1- Fluoroethyl, cyclopropyl, cyclohexyl, allyl, propargyl, methoxyethyl, ethoxyethyl, acetoxyethyl, acryloxyethyl, methacryloxy , Dimethylaminoethyl, diisopropylaminoethyl, methylaminoethyl, ethylaminoethyl, isopropylaminoethyl, tert-butylaminoethyl, tetrahydrofuranmethylene, unsubstituted or 1-2 Independently selected from the phenyl substituted by the following groups: fluorine, chlorine or bromine;R 8选自氢、C 1-C 4烷基羰基、C 1-C 4卤代烷基羰基、环丙甲酰基、C 1-C 4烷基磺酰基、C 1-C 4卤代烷基磺酰基、二(C 1-C 2)烷基氨基磺酰基、二(C 1-C 3)烷基氨基羰基、C 1-C 2烷硫基C 2-C 4烷基羰基、苯乙酰基、苯丙酰基、2-甲基-4-氯苯氧乙酰基、2,4-二氯苯氧乙酰基、
R 8 is selected from hydrogen, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, cyclopropanoyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, two (C 1 -C 2 )alkylaminosulfonyl, di(C 1 -C 3 )alkylaminocarbonyl, C 1 -C 2 alkylthio, C 2 -C 4 alkylcarbonyl, phenylacetyl, phenylpropionyl , 2-Methyl-4-chlorophenoxyacetyl, 2,4-dichlorophenoxyacetyl,
R 9选自氢、甲基、乙基、异丙基、正丙基、正丁基、叔丁基、三氟乙基、二氟乙基、1-氯乙基、1-氯丙基或2-氯丙基； R 9 is selected from hydrogen, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, trifluoroethyl, difluoroethyl, 1-chloroethyl, 1-chloropropyl or 2-chloropropyl;R 10选自氢、甲基、乙基、异丙基、正丙基、正丁基、叔丁基、甲氧基羰基亚甲基、乙氧基羰基亚甲基、SO 2NHCH 3、SO 2NHC 2H 5、SO 2N(CH 3) 2或SO 2N(CH 3)[CH(CH 3) 2]； R 10 is selected from hydrogen, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, methoxycarbonylmethylene, ethoxycarbonylmethylene, SO 2 NHCH 3 , SO 2 NHC 2 H 5 , SO 2 N(CH 3 ) 2 or SO 2 N(CH 3 )[CH(CH 3 ) 2 ];Q选自如下Q1、Q2、Q3、Q4、Q5、Q6、Q7或Q8；Q is selected from the following Q1, Q2, Q3, Q4, Q5, Q6, Q7 or Q8;R 11选自甲基、乙基、异丙基、叔丁基、二氟甲基、三氟乙基或二氟乙基； R 11 is selected from methyl, ethyl, isopropyl, tert-butyl, difluoromethyl, trifluoroethyl or difluoroethyl;R 12选自甲基、三氟甲基、二氟甲基、甲氧基、异丙氧基、三氟甲氧基、二氟甲氧基、三氟乙氧基或者二氟乙氧基； R 12 is selected from methyl, trifluoromethyl, difluoromethyl, methoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, trifluoroethoxy or difluoroethoxy;R 13选自氢、氯、溴或甲基； R 13 is selected from hydrogen, chlorine, bromine or methyl;R 14选自甲基、乙基、正丙基、异丙基、异丁基或叔丁基； R 14 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl or tert-butyl;或，具有羧基的式(I)化合物的可农用盐或衍生物。Or, an agriculturally acceptable salt or derivative of the compound of formula (I) having a carboxyl group. - 按照权利要求6所述的化合物，其特征在于：通式(I)中The compound according to claim 6, characterized in that: in the general formula (I)R 1、R 2分别选自氢、氟或氯； R 1 and R 2 are each selected from hydrogen, fluorine or chlorine;R 3选自氢、甲基或乙基； R 3 is selected from hydrogen, methyl or ethyl;R 4选自氢或甲基； R 4 is selected from hydrogen or methyl;R 5选自氢、甲基、乙基、三氟甲基、CH 2CO 2CH 3、CH 2CO 2C 2H 5、CO 2CH 3、CO 2C 2H 5或CH 2SiC(CH 3) 3； R 5 is selected from hydrogen, methyl, ethyl, trifluoromethyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5 , CO 2 CH 3 , CO 2 C 2 H 5 or CH 2 SiC (CH 3 ) 3 ;R 6选自氢、氰基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、甲氧基、环丙基、CH 2CO 2CH 3、CH 2CO 2C 2H 5、CH 2CH 2CO 2CH 3、CH 2CH 2CO 2C 2H 5或CO 2R 7； R 6 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, cyclopropyl, CH 2 CO 2 CH 3 , CH 2 CO 2 C 2 H 5 , CH 2 CH 2 CO 2 CH 3 , CH 2 CH 2 CO 2 C 2 H 5 or CO 2 R 7 ;R 5、R 6可与相邻的C连接形成四氢呋喃酮环； R 5 and R 6 can be connected with adjacent C to form a tetrahydrofuranone ring;R 3、R 5可与相邻的C连接形成环戊烷或环己烷； R 3 and R 5 can be connected with adjacent C to form cyclopentane or cyclohexane;R 7选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、三氟乙基、二氟乙基、1-氯乙基、1-氟乙基、环丙基、环己基、烯丙基、炔丙基、甲氧基乙基、乙氧基乙基、乙酰氧基乙基、丙烯酰氧基乙基、甲基丙烯酰氧基、二甲氨基乙基、二异丙基氨基乙基、甲氨基乙基、乙氨基乙基、异丙氨基乙基、叔丁氨基乙基、四氢呋喃亚甲基、未取代或被1-2个独立选自以下基团取代的苯基：氟、氯或溴。 R 7 is selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, trifluoroethyl, difluoroethyl, 1-chloroethyl, 1- Fluoroethyl, cyclopropyl, cyclohexyl, allyl, propargyl, methoxyethyl, ethoxyethyl, acetoxyethyl, acryloxyethyl, methacryloxy , Dimethylaminoethyl, diisopropylaminoethyl, methylaminoethyl, ethylaminoethyl, isopropylaminoethyl, tert-butylaminoethyl, tetrahydrofuranmethylene, unsubstituted or 1-2 Independently selected from phenyl substituted by the following groups: fluorine, chlorine or bromine.Q选自如下Q1、Q2、Q3、Q4、Q5、Q6、Q7或Q8；Q is selected from the following Q1, Q2, Q3, Q4, Q5, Q6, Q7 or Q8;R 11选自甲基或二氟甲基； R 11 is selected from methyl or difluoromethyl;R 12选自甲基、三氟甲基、二氟甲基、异丙氧基、二氟甲氧基、三氟乙氧基或者二氟乙氧基； R 12 is selected from methyl, trifluoromethyl, difluoromethyl, isopropoxy, difluoromethoxy, trifluoroethoxy or difluoroethoxy;R 13选自氯、溴或甲基； R 13 is selected from chlorine, bromine or methyl;R 14选自甲基、异丙基、异丁基或叔丁基； R 14 is selected from methyl, isopropyl, isobutyl or tert-butyl;或，具有羧基的式(I)化合物的可农用盐或衍生物。Or, an agriculturally acceptable salt or derivative of the compound of formula (I) having a carboxyl group.
- 一种根据权利要求1所述的通式(I)化合物用于防治杂草的应用。An application of the compound of general formula (I) according to claim 1 for controlling weeds.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911039269.X | 2019-10-29 | ||
| CN201911039269 | 2019-10-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2021082901A1 true WO2021082901A1 (en) | 2021-05-06 |
Family
ID=75645458
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/CN2020/120564 WO2021082901A1 (en) | 2019-10-29 | 2020-10-13 | Phenylisoxazoline compound and use thereof |
Country Status (3)
| Country | Link |
|---|---|
| CN (1) | CN112745269B (en) |
| AR (1) | AR120325A1 (en) |
| WO (1) | WO2021082901A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112021023672A2 (en) * | 2020-01-16 | 2022-08-02 | Qingdao Kingagroot Chemical Compound Co Ltd | AN AROMATIC COMPOUND SUBSTITUTED BY FUSED RING, PREPARATION METHOD, HERBICIDAL COMPOSITION AND USE THEREOF |
| CN115433177A (en) * | 2021-06-03 | 2022-12-06 | 沈阳中化农药化工研发有限公司 | Aryl isoxazoline compound and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1413209A (en) * | 1999-12-22 | 2003-04-23 | 巴斯福股份公司 | 3-(4.5-dihydroisoxazole-5-yl)-benzoylpyrazole |
| WO2016095768A1 (en) * | 2014-12-16 | 2016-06-23 | 沈阳中化农药化工研发有限公司 | Pyrimidine urea compound containing isoxazolines and use thereof |
| CN105777733A (en) * | 2014-12-16 | 2016-07-20 | 沈阳中化农药化工研发有限公司 | Isoxazoline-containing tetrahydrophthalimide compound and use thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2704662B2 (en) * | 1989-11-07 | 1998-01-26 | 日本農薬株式会社 | 3-Substituted phenylpyrazole derivatives or salts thereof and uses thereof |
| DE4417837A1 (en) * | 1994-05-20 | 1995-11-23 | Basf Ag | Substituted 3-phenylpyrazoles |
| MX2015003538A (en) * | 2012-09-25 | 2015-10-12 | Bayer Cropscience Ag | 3-phenylisoxazolin derivatives with herbicidal action. |
-
2020
- 2020-10-13 WO PCT/CN2020/120564 patent/WO2021082901A1/en active Application Filing
- 2020-10-13 CN CN202011088748.3A patent/CN112745269B/en active Active
- 2020-10-28 AR ARP200102981A patent/AR120325A1/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1413209A (en) * | 1999-12-22 | 2003-04-23 | 巴斯福股份公司 | 3-(4.5-dihydroisoxazole-5-yl)-benzoylpyrazole |
| WO2016095768A1 (en) * | 2014-12-16 | 2016-06-23 | 沈阳中化农药化工研发有限公司 | Pyrimidine urea compound containing isoxazolines and use thereof |
| CN105777733A (en) * | 2014-12-16 | 2016-07-20 | 沈阳中化农药化工研发有限公司 | Isoxazoline-containing tetrahydrophthalimide compound and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN112745269A (en) | 2021-05-04 |
| CN112745269B (en) | 2023-01-24 |
| AR120325A1 (en) | 2022-02-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105753853B (en) | Isoxazoline-containing uracil compound and application thereof | |
| TWI598344B (en) | Herbicidally active 3-phenylisoxazoline derivatives | |
| CZ282051B6 (en) | 4-bonzoylisoxazole derivative, process of its preparation, herbicidal agent contained therein and method of controlling weed | |
| TW200804291A (en) | Novel microbiocides | |
| JP2011510928A (en) | Bactericidal heterocyclic compounds | |
| TWI647216B (en) | Substituted pyrazolylpyrazole derivative and use of same as herbicide | |
| DK3160945T3 (en) | HERBICID-EFFECTIVE ARYLCARBOXYLIC ACIDAMIDS | |
| JPH08208620A (en) | Aminopyrazole derivative, its production and use | |
| WO2021082901A1 (en) | Phenylisoxazoline compound and use thereof | |
| TW201638076A (en) | Novel isothiazolamides, processes for their preparation and their use as herbicides and/or plant growth regulators | |
| ES2691948T3 (en) | Amides of n- (1-methyltetrazol-5-yl) benzoic acid with herbicidal action | |
| JPH06271553A (en) | New herbicide | |
| JPH06192015A (en) | New herbicide | |
| WO2021073487A1 (en) | Isoxazoline compound having optical activity and use thereof | |
| TW200301078A (en) | N-heteroaryl nicotinamid derivatives | |
| US7273878B2 (en) | Difluoroalkene derivative, pest control agent containing the same, and intermediate therefor | |
| JPH05255284A (en) | New herbicide | |
| KR940011137B1 (en) | Cyclohexane herbicides | |
| JP6934817B2 (en) | Herbicidal compound | |
| CN109553615B (en) | Pyrimidine salt compound and application thereof | |
| US10743540B2 (en) | 3-amino-1,2,4-triazine derivatives and their use for controlling undesired plant growth | |
| WO2022253362A1 (en) | Aryl isoxazoline compound and use thereof | |
| JP2017523236A (en) | Benzoamides with herbicidal activity | |
| JP2002515895A (en) | Phenoxyacetic acid derivatives and their use as herbicides | |
| JP6763877B2 (en) | Herbicidal compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 20882007 Country of ref document: EP Kind code of ref document: A1 |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 20882007 Country of ref document: EP Kind code of ref document: A1 |