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CN-122004216-A - Herbicide composition containing cyclohexene diketone lactic acid oxime ether derivative and application thereof

CN122004216ACN 122004216 ACN122004216 ACN 122004216ACN-122004216-A

Abstract

The invention discloses a pesticide composition, which contains cyclohexene diketone lactic acid oxime ether compound shown in formula I, stereoisomer, tautomer, solvate or acceptable salt thereof in pesticide, And herbicide B, wherein R 1 -R 4 and herbicide B are as defined in the specification. The composition disclosed by the invention has a good weeding effect and a good application prospect.

Inventors

  • DENG ZHAOXI
  • LI ZHIHAO
  • Yao Shengtang
  • HE YUNMENG
  • Hu Hewei
  • CEN JIN
  • YANG LINA
  • LI JUNPEI
  • WANG JUNKE
  • LI ZHIJUN
  • Tian Chaoge
  • Allen mak

Assignees

  • 郑州手性药物研究院有限公司

Dates

Publication Date
20260512
Application Date
20241112

Claims (11)

  1. 1. A pesticide composition is characterized in that, Comprising a compound of formula I, a stereoisomer, tautomer or salt thereof, Wherein R 1 is H, optionally substituted C 1 -C 6 alkyl, optionally substituted C 1 -C 6 alkoxy, optionally substituted C 1 -C 6 thio, optionally substituted C 1 -C 6 alkoxy-C 1 -C 6 alkyl, optionally substituted C 1 -C 6 alkylthio-C 1 -C 6 alkyl, optionally substituted C 3 -C 6 cycloalkyloxy-C 1 -C 6 alkyl, optionally substituted C 3 -C 6 cycloalkylthio-C 1 -C 6 alkyl, optionally substituted C 3 -C 6 cycloalkyl, optionally substituted heterocyclyl; R 2 is optionally substituted C 1 -C 6 alkyl, optionally substituted C 3 -C 6 cycloalkyl; r 3 is optionally substituted C 1 -C 6 alkyl, optionally substituted C 2 -C 6 alkenyl, optionally substituted C 3 -C 6 cycloalkyl; R 4 is H, optionally substituted C 1 -C 6 alkyl, optionally substituted C 2 -C 6 alkenyl, optionally substituted phenyl, optionally substituted heterocyclyl; And the herbicide B, The herbicide B is one or more selected from the following herbicides: The sulfonylurea herbicide is preferably nicosulfuron, carbosulfuron, epoxy-azosulfuron, thifensulfuron methyl, metsulfuron methyl, ether sulfuron methyl, chlorsulfuron, ethametsulfuron methyl, tetrazole sulfuron methyl, trifloxysulfuron, propylsulfuron, chlorimuron, ethoxysulfuron, fluazuron, cyclosulfamuron, pyrazosulfuron, bensulfuron methyl, halosulfuron methyl, sulfosulfuron methyl, methyl-disulfuron, acyl-sulfuron methyl, or flazasulfuron methyl; Amide herbicides; the amide herbicide is preferably alachlor, acetochlor, metolachlor, pretilachlor, butachlor acetochlor, diflufenican, barnyard grass, isoxaflutole, flupyraclostrobin ethaboxam, diflufenican, barnyard grass amine clomazone, flupyraclonil; The aryloxy-phenoxy-propionic acid herbicide is cyhalofop-butyl, quizalofop-p-ethyl, metamifop-ethyl, oxadiazon-ethyl or clodinafop-propargyl; The cyclohexenone/trione herbicide is preferably selected from the group consisting of triclosan, sethoxydim, pyrone, thioxanthone, phenone, cyclobenone, clethodim, fenpropione, gramoxydim, sulcotrione, mesotrione, cyclosulcotrione and bicyclosultone; Triazolopyrimidine herbicides; the triazolopyrimidine herbicide is preferably florasulam sulfenamide, mefenacet methoxysulfonic acid oxadiazon (L); Carboxylic acid herbicides; such as 2.4-D, 2-methyl-4-chloro, 2,4,5-T, dicamba, dichlorvos, picloram, clopyralid, aminopyralid, triclopyr and salts thereof, butoxyethyl triclopyr, fluroxypyr, isooctyl fluroxypyr, or quinclorac; Diphenyl ether herbicides; the diphenyl ether herbicide is preferably fomesafen, fluoroglycofen-ethyl, oxyfluorfen, lactofen, fluoroxyfen-ethyl or fluoroxyfen; A triazine herbicide; the triazobenzene herbicide is preferably terbutryn, isoprotujing, fluben, glycyrrhizin, ametryn, simazine, prometryn, atrazine, simetryn or triazophos; Other types of herbicides; the other herbicide is preferably isoxaflutole, clomazone, oxadiazon fludioxonil, oxazin, oxadiargyl, cyclopentaoxadiazon, bentazone, fludioxonil, oxazin, oxadiargyl oxadiazon, bentazone, and process for preparing.
  2. 2. The composition of claim 1 wherein R 1 is -H、-CH 3 、-C 2 H 5 、-C 3 H 7 、-C 4 H 9 、-C 5 H 11 、-C 6 H 13 、-Q-CH 3 、-Q-C 2 H 5 、-CH 2 -Q-CH 3 、-Q-C 3 H 7 、-C 2 H 4 -Q-CH 3 、-CH 2 -Q-C 2 H 5 、-Q-C 4 H 9 、-CH 2 -Q-C 3 H 7 、-C 2 H 4 -Q-C 2 H 5 、-C 3 H 6 -Q-CH 3 、-Q-C 5 H 11 、-CH 2 -Q-C 4 H 9 、-CH 2 -Q-C 4 H 9 、-C 2 H 4 -Q-C 3 H 7 、-C 3 H 6 -Q-C 2 H 5 、-C 4 H 8 -Q-CH 3 、-Q-C 6 H 13 、-CH 2 -Q-C 5 H 11 、-C 2 H 4 -Q-C 4 H 9 、-C 3 H 6 -Q-C 3 H 7 、-C 4 H 8 -Q-C 2 H 5 、-C 5 H 10 -Q-CH 3 、 Wherein Q is O or S, X is C, O or S, Y is C 1 -C 3 alkyl, n is selected from integers from 0 to 3, preferably -CH 3 、-CH 2 CH 2 CH 3 、-CH 2 CH 2 CH 2 CH 3 、-CH 2 -O-CH 3 、-CH 2 -O-CH 2 CH 3 、-CH 2 -S-CH 3 、-CH 2 CH 2 -S-CH 3 、-CH 2 CH(CH 3 )SCH 2 CH 3 、
  3. 3. The composition according to claim 1 or 2, wherein R 2 is -CH 3 、-C 2 H 5 、-C 3 H 7 、-C 4 H 9 、-C 5 H 11 、-C 6 H 13 、 Wherein n is selected from integers from 0 to 3 and Y is C 1 -C 3 alkyl, preferably -CH 3 、-CH 2 CH 3 、-CH 2 CH 2 CH 3 、-CH(CH 3 )CH 2 CH 3 、 -CH(CH 3 ) 2 、-CH(CH 3 )CH(CH 3 )CH 3 、-CH 2 CH 2 CH(CH 3 ) 2 .
  4. 4. A composition according to any one of claims 1 to 3, wherein R 3 is -CH 3 、-C 2 H 5 、-C 3 H 7 、-C 4 H 9 、-C 5 H 11 、-C 6 H 13 、-CH＝CHCH 3 、-CH 2 CH＝CH 2 、-CH 2 CH＝CHZ、-CH＝CHCH 2 Z、 Wherein Z is F, cl, br, I, n is an integer from 0 to 3, Y is C 1 -C 3 alkyl, preferably -CH 3 、-CH 2 CH 3 、-CH 2 CH 2 CH 3 、-CH(CH 3 ) 2 、-CH 2 CH 2 CH 2 CH 3 、-CH(CH 3 )CH 2 CH 3 、-CH 2 CH(CH 3 ) 2 、-C(CH 3 ) 3 、-CH 2 CH 2 CH 2 CH 2 CH 3 、-CH(CH 3 )CH 2 CH 2 CH 3 、-CH 2 CH(CH 3 )CH 2 CH 3 、-CH 2 CH 2 CH(CH 3 ) 2 、-C(CH 3 ) 2 CH 2 CH 3 、-CH 2 C(CH 3 ) 3 、-CH(CH 2 CH 3 )CH 2 CH 3 、-CH 2 CH(CH 2 CH 3 )CH 3 .
  5. 5. The composition of any one of claims 1-4, wherein R 4 is -H、-CH 3 、-C 2 H 5 、-C 3 H 7 、-C 4 H 9 、-C 5 H 11 、-C 6 H 13 、-CH 2 CH＝CH 2 、-CH 2 CH＝CHZ、 Wherein P is selected from H, -CH 3 、-C 2 H 5 、-C 3 H 7 、-Cl、-F、-Br、-I、-CN、-NO 2 or-CF 3 , n is selected from integers from 0 to 3, Z is selected from F, cl, br, I, R 4 is preferably -H、-CH 3 、-CH 2 CH 3 、-CH 2 CH 2 CH 3 、-CH(CH 3 ) 2 、-CH 2 CH 2 CH 2 CH 3 、-CH(CH 3 )CH 2 CH 3 、-CH 2 CH(CH 3 ) 2 、-C(CH 3 ) 3 、-CH 2 CH 2 CH 2 CH 2 CH 3 、-CH(CH 3 )CH 2 CH 2 CH 3 、-CH 2 CH(CH 3 )CH 2 CH 3 、-CH 2 CH 2 CH 2 (CH 3 ) 2 、-C(CH 3 ) 2 CH 2 CH3、-CH 2 C(CH 3 ) 3 、-CH(CH 2 CH 3 )CH 2 CH 3 、-CH 2 CH(CH 2 CH 3 )CH 3 、
  6. 6. The composition according to any one of claims 1 to 5, wherein formula I is selected from the following compounds:
  7. 7. The composition according to any one of claims 1 to 6, wherein the weight ratio of the compound of formula I, its stereoisomers, tautomers or salts thereof to herbicide B is from 1:100 to 50:1.
  8. 8. The composition of claim 7, wherein the herbicide B is selected from one or more of rimsulfuron, cyhalofop-butyl, fomesafen, flurbiproflumilast, florasulam, clethodim, atrazine, and benazolin.
  9. 9. The composition according to any one of claim 1 to 8, Preferably, the pesticide composition contains a compound 1 and rimsulfuron, wherein the weight ratio of the compound 1 to rimsulfuron is 1:10 to 10:1, preferably 1:10 to 1:2, particularly preferably 1:10, 1:5, 1:4, 1:2, wherein the compound 1 has the following structure: Preferably, the pesticide composition contains compound 2 and cyhalofop-butyl, wherein the weight ratio of compound 2 to cyhalofop-butyl is 1:100 to 10:1, preferably 1:50 to 1:1, particularly preferably 1:50, 1:25, 1:10, 1:5, 1:2 and 1:1, wherein the compound 2 has the following structure Preferably, the pesticide composition contains compound 3 and fomesafen, wherein the weight ratio of compound 3 to fomesafen is 1:50 to 5:1, preferably 1:37.5 to 1:2.5, particularly preferably 1:37.5, 1:10, 1:5 and 1:2.5, wherein the structure of compound 3 is as follows Preferably, the pesticide composition contains compound 4 and a chlorofluoropyridine ester, wherein the weight ratio of compound 4 to chlorofluoropyridine ester is 1:100-1:1, preferably 1:50-1:5, particularly preferably 1:50, 1:15, 1:10 and 1:5, wherein compound 4 has the structure Preferably, the pesticide composition contains compound 5 and florasulam, wherein the weight ratio of compound 5 to florasulam is 1:10-10:1, preferably 1:1.5-2.5:1, particularly preferably 1:1.5, 1:1, 2:1 and 2.5:1, wherein the structure of compound 5 is as follows Preferably, the pesticide composition contains compound 6 and flufenacet, wherein the weight ratio of compound 6 to flufenacet is 1:100-10:1, preferably 1:50-1:7.5, particularly preferably 1:50, 1:30, 1:15 and 1:7.5, wherein the structure of compound 6 is as follows Preferably, the pesticide composition contains compound 7 and clethodim, wherein the weight ratio of compound 7 to clethodim is 1:100-10:1, preferably 1:60-1:5, particularly preferably 1:60, 1:30, 1:10 and 1:5, wherein the compound 7 has the following structure Preferably, the pesticide composition contains compound 8 and atrazine, wherein the weight ratio of compound 8 to atrazine is 1:100 to 10:1, preferably 1:60 to 1:20, particularly preferably 1:60, 1:30 and 1:20, wherein the structure of compound 8 is as follows Preferably, the pesticide composition contains compound 9 and cyhalofop-butyl, wherein the weight ratio of compound 9 to cyhalofop-butyl is 1:50 to 10:1, preferably 1:12.5 to 2.5:1, particularly preferably 1:12.5, 1:5, 1:1 and 2.5:1, wherein the structure of compound 9 is as follows Preferably, the pesticide composition contains compound 10 and benazolin, wherein the weight ratio of compound 10 to benazolin is 1:100 to 10:1, preferably 1:40 to 1:5, particularly preferably 1:40, 1:20, 1:10 and 1:5, wherein compound 10 has the structure
  10. 10. The composition according to any one of claims 1 to 9, wherein the composition further comprises a pesticidally acceptable adjuvant, preferably formulated into a suitable dosage form, preferably one of an emulsifiable concentrate, an aqueous emulsion, a suspension, a water-based formulation, a water-dispersible granule, a powder, a wettable powder, a soluble powder/granule, a granule.
  11. 11. The composition according to any one of claims 1 to 10, further comprising a safener C, preferably selected from the group consisting of clomazone, benoxacor, furbenoxacor, benoxacor nitrile, benoxanitrile, oryzalin, benoxamide, clomazone, mefenacet, 1, 8-naphthalenedicarboxylic anhydride, dichloropropylamine, benoxazidine, metcamifen, 5-phenyl-4, 5-dihydroisoxazole-3-carboxylic acid ethyl ester.

Description

Herbicide composition containing cyclohexene diketone lactic acid oxime ether derivative and application thereof Technical Field The invention belongs to the field of agriculture, and particularly relates to a herbicide composition containing cyclohexene diketone lactic acid oxime ether derivatives and application thereof. Background Cyclohexanediones are a large class of substances having a wide range of biological activities such as herbicidal, bactericidal, insecticidal, etc., among which herbicidal activity is the most interesting. Cyclohexanedione herbicides are mainly divided into two types, one is a 2-acyl-1, 3-cyclohexanedione compound which is an HPPD inhibitor and has broad-spectrum weeding activity, and the other is an oxime ether type 1, 3-cyclohexanedione compound which is an ACCase inhibitor and is used for preventing and killing annual or perennial grassy weeds. Compounds comprising cyclohexanedione structures are known to be clethodim, sethoxydim, graminezide, thioxanthone, butoxycyclic ketone, triclopyr, pyrone and fenpropion. But develops resistance on many weeds due to long-term use. Those skilled in the art are continually looking for suitable alternative pesticide herbicides. The patent (CN 115417791B) published by the applicant discloses an oxime ether type 1, 3-cyclohexanedione compound and a synthetic method and application thereof, wherein the structure of the compound is as follows: Compound 8 disclosed therein: the weeding composition has good weeding effect and safety to crops. Lactic acid is used as an important active substance in human body, can be applied to various fields of medicines, materials, foods and the like, and the applicant researches find that lactic acid or lactic acid derivative fragments replace known modified structural fragments to be connected with cyclohexene diketone through oximation reaction to obtain a lactic acid oxime ether compound, which has high weeding activity and safety and good control effect on resistant weeds. Disclosure of Invention The invention discloses a pesticide composition, which contains a compound of a formula I, a stereoisomer, a tautomer or a salt thereof, Wherein R 1 is H, optionally substituted C 1-C6 alkyl, optionally substituted C 1-C6 alkoxy, optionally substituted C 1-C6 thio, optionally substituted C 1-C6 alkoxy-C 1-C6 alkyl, optionally substituted C 1-C6 alkylthio-C 1-C6 alkyl, optionally substituted C 3-C6 cycloalkyloxy-C 1-C6 alkyl, optionally substituted C 3-C6 cycloalkylthio-C 1-C6 alkyl, optionally substituted C 3-C6 cycloalkyl, optionally substituted heterocyclyl; R 2 is optionally substituted C 1-C6 alkyl, optionally substituted C 3-C6 cycloalkyl; r 3 is optionally substituted C 1-C6 alkyl, optionally substituted C 2-C6 alkenyl, optionally substituted C 3-C6 cycloalkyl; R 4 is H, optionally substituted C 1-C6 alkyl, optionally substituted C 2-C6 alkenyl, optionally substituted phenyl, optionally substituted heterocyclyl; And the herbicide B, The herbicide B is one or more selected from the following herbicides: The sulfonylurea herbicide is preferably nicosulfuron, carbosulfuron, epoxy-azosulfuron, thifensulfuron methyl, metsulfuron methyl, ether sulfuron methyl, chlorsulfuron, ethametsulfuron methyl, tetrazole sulfuron methyl, trifloxysulfuron, propylsulfuron, chlorimuron, ethoxysulfuron, fluazuron, cyclosulfamuron, pyrazosulfuron, bensulfuron methyl, halosulfuron methyl, sulfosulfuron methyl, methyl-disulfuron, acyl-sulfuron methyl, or flazasulfuron methyl; Amide herbicides; the amide herbicide is preferably alachlor, acetochlor, metolachlor, pretilachlor, butachlor acetochlor, diflufenican, barnyard grass, isoxaflutole, flupyraclostrobin ethaboxam, diflufenican, barnyard grass amine clomazone, flupyraclonil; The aryloxy-phenoxy-propionic acid herbicide is cyhalofop-butyl, quizalofop-p-ethyl, metamifop-ethyl, oxadiazon-ethyl or clodinafop-propargyl; The cyclohexenone/trione herbicide is preferably selected from the group consisting of triclosan, sethoxydim, pyrone, thioxanthone, phenone, cyclobenone, clethodim, fenpropione, gramoxydim, sulcotrione, mesotrione, cyclosulcotrione and bicyclosultone; Triazolopyrimidine herbicides; the triazolopyrimidine herbicide is preferably florasulam sulfenamide, mefenacet methoxysulfonic acid oxadiazon (L); Carboxylic acid herbicides; such as 2.4-D, 2-methyl-4-chloro, 2,4,5-T, dicamba, dichlorvos, picloram, clopyralid, aminopyralid, triclopyr and salts thereof, butoxyethyl triclopyr, fluroxypyr, isooctyl fluroxypyr, or quinclorac; Diphenyl ether herbicides; the diphenyl ether herbicide is preferably fomesafen, fluoroglycofen-ethyl, oxyfluorfen, lactofen, fluoroxyfen-ethyl or fluoroxyfen; A triazine herbicide; the triazobenzene herbicide is preferably terbutryn, isoprotujing, fluben, glycyrrhizin, ametryn, simazine, prometryn, atrazine, simetryn or triazophos; Other types of herbicides; the other herbicide is preferably isoxaflutole, clomazone, oxadiazon fludioxonil, oxazin, oxad