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CN-121991050-A - Fused heterocyclic compound, preparation method thereof, weeding composition and application

CN121991050ACN 121991050 ACN121991050 ACN 121991050ACN-121991050-A

Abstract

The invention belongs to the technical field of pesticides, and particularly relates to a fused heterocyclic compound, a preparation method thereof, a weeding composition and application thereof. The compound is shown in a general formula I: Wherein X represents O or S, Y represents a direct bond or CR 7 R 8 ;R 1 represents a haloalkyl group, R 4 represents a halogen, R 6 represents a cycloalkylalkyl group, R 2 、R 3 、R 5 、R 7 、R 8 each independently represents hydrogen, halogen, alkyl, alkenyl, or the like. The compound has excellent herbicidal activity and crop safety.

Inventors

  • LIAN LEI
  • PENG XUEGANG
  • ZHAO DE
  • HUA RONGBAO

Assignees

  • 青岛清原化合物有限公司

Dates

Publication Date
20260508
Application Date
20250926
Priority Date
20241105

Claims (9)

  1. 1. A fused heterocyclic compound represented by the general formula I: Wherein X represents O or S; y represents a direct bond or CR 7 R 8 ; R 1 represents haloalkyl, R 4 represents halogen, R 6 represents cycloalkylalkyl; R 2 、R 3 、R 5 、R 7 、R 8 each independently represents hydrogen, halogen, alkyl, alkenyl, alkynyl, cyano, nitro, cycloalkyl, aryl, heterocyclyl, -OR, -SR, -SOR, - (SO 2 )R、-N(R) 2 , -O (CO) R, -O (CO) OR, - (CO) R, OR- (CO) N (R) 2 , OR R 7 and R 8 together form an alkylene group, the alkyl, alkenyl, OR alkynyl being optionally substituted with at least one group selected from halogen, cyano, nitro, cycloalkyl, aryl, heterocyclyl, -OR, -SR, -SOR, - (SO 2 )R、-N(R) 2 , -O (CO) R, -O (CO) OR, - (CO) R, OR- (CO) N (R) 2 ; The foregoing "cycloalkyl", "heterocyclyl" OR "aryl" is optionally substituted with at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, -OR, -SR, - (CO) R, - (CO) OR, - (CO) N (R) 2 、-(CS)N(R) 2 , - (SO) R OR- (SO 2 ) R; r independently represents hydrogen, alkyl, alkenyl, alkynyl, alkyl, alkenyl or alkynyl substituted by at least one group selected from halogen, hydroxy, alkoxy, cyano or alkoxycarbonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy.
  2. 2. The fused heterocyclic compound as described in claim 1, wherein, R 1 represents a halogenated C1-C8 alkyl group, R 6 represents a C3-C8 cycloalkyl C1-C8 alkyl group; R 2 、R 3 、R 5 、R 7 、R 8 each independently represents hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, cyano, nitro, C3-C8 cycloalkyl, aryl, heterocyclyl, -OR, -SR, -SOR, - (SO 2 )R、-N(R) 2 , -O (CO) R, -O (CO) OR, - (CO) R, OR- (CO) N (R) 2 , OR R 7 and R 8 together form C1-C8 alkylene, the C1-C8 alkyl, C2-C8 alkenyl, OR C2-C8 alkynyl being optionally substituted with at least one group selected from halogen, cyano, nitro, C3-C8 cycloalkyl, aryl, heterocyclyl, -OR, -SR, -SOR, - (SO 2 )R、-N(R) 2 , -O (CO) R, -O (CO) OR, - (CO) R, OR- (CO) N (R) 2 ; The foregoing "C3-C8 cycloalkyl", "heterocyclyl" OR "aryl" is optionally substituted with at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, haloC 1-C8 alkyl, haloC 2-C8 alkenyl, haloC 2-C8 alkynyl, -OR, -SR, - (CO) R, - (CO) OR, - (CO) N (R) 2 、-(CS)N(R) 2 , - (SO) R OR- (SO 2 ) R; R independently of one another represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkyl substituted by at least one radical selected from halogen, hydroxy, C1-C8 alkoxy, cyano or C1-C8 alkoxycarbonyl, C2-C8 alkenyl or C2-C8 alkynyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl C1-C8 alkyl, phenyl or phenyl substituted by at least one radical selected from halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halogenated C1-C8 alkoxy.
  3. 3. The fused heterocyclic compound as described in claim 1, wherein, R 1 represents a halogenated C1-C6 alkyl group, R 6 represents a C3-C6 cycloalkyl C1-C6 alkyl group; R 2 、R 3 、R 5 、R 7 、R 8 each independently represents hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cyano, nitro, C3-C6 cycloalkyl, aryl, heterocyclyl, -OR, -SR, -SOR, - (SO 2 )R、-N(R) 2 , -O (CO) R, -O (CO) OR, - (CO) R, OR- (CO) N (R) 2 , OR R 7 and R 8 together form C1-C6 alkylene, the C1-C6 alkyl, C2-C6 alkenyl, OR C2-C6 alkynyl being optionally substituted with at least one group selected from halogen, cyano, nitro, C3-C6 cycloalkyl, aryl, heterocyclyl, -OR, -SR, -SOR, - (SO 2 )R、-N(R) 2 , -O (CO) R, -O (CO) OR, - (CO) R, OR- (CO) N (R) 2 ; the foregoing "C3-C6 cycloalkyl", "heterocyclyl" OR "aryl" is optionally substituted with at least one group selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, haloC 1-C6 alkyl, haloC 2-C6 alkenyl, haloC 2-C6 alkynyl, -OR, -SR, - (CO) R, - (CO) OR, - (CO) N (R) 2 、-(CS)N(R) 2 , - (SO) R OR- (SO 2 ) R; R independently of one another represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkyl substituted by at least one radical selected from halogen, hydroxy, C1-C6 alkoxy, cyano or C1-C6 alkoxycarbonyl, C2-C6 alkenyl or C2-C6 alkynyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl C1-C6 alkyl, phenyl or phenyl substituted by at least one radical selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy; Preferably, the compound is selected from any one of table 1 of the specification.
  4. 4. A process for the preparation of a fused heterocyclic compound as described in any one of claims 1 to 3, comprising the steps of: the compound shown in the general formula II and the compound shown in the general formula III react to obtain the compound shown in the general formula I, and the reaction equation is as follows: Wherein the substituents R 1 、R 2 、R 3 、R 4 、R 5 、R 6 , X and Y are as defined in any of claims 1 to 3. Preferably, the reaction is performed in the presence of a base and a solvent, more preferably, the base is selected from at least one of an inorganic base or an organic base, and the solvent is selected from at least one of an aromatic hydrocarbon (such as benzene, chlorobenzene or toluene), DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, dioxane, dichloromethane, toluene or ethyl acetate.
  5. 5. The method according to claim 4, wherein, (1) The compound shown in the general formula II is prepared by reacting a compound shown in the general formula IV with a compound shown in the general formula V, and the reaction equation is as follows: or (2) the compound shown in the general formula II is prepared by reacting the compound shown in the general formula VI with the compound shown in the general formula VII, and the reaction equation is as follows: wherein W each independently represents a C1-C6 alkyl group, an aryl group or an arylC 1-C6 alkyl group which is unsubstituted or substituted with any one selected from the group consisting of an alkyl group, a halogen group, an alkoxy group, a haloalkyl group and a cyano group; Preferably, the reaction (1) is carried out under acidic conditions, or the reaction (2) is carried out in the presence of a solvent and a base, more preferably, the acid is selected from at least one of an inorganic acid or an organic acid, or the base is selected from at least one of an inorganic base or an organic base, or the solvent is selected from at least one of an aromatic hydrocarbon (such as toluene, xylene), DMF, DMA, THF, acetonitrile, dichloroethane, DMSO, dioxane, dichloromethane or ethyl acetate.
  6. 6. A herbicidal composition comprising a herbicidally effective amount of at least one of the fused heterocyclic compounds as described in any of claims 1 to 3, preferably further comprising formulation adjuvants, more preferably further comprising other active ingredients.
  7. 7. A method of controlling weeds which comprises applying a herbicidally effective amount of at least one of the fused heterocyclic compounds as described in any one of claims 1 to 3 or the herbicide composition as described in claim 6 to plants or to weed areas.
  8. 8. Use of a fused heterocyclic compound as described in any one of claims 1-3 or a composition as described in claim 6 for controlling weeds, preferably for controlling weeds in crops of useful plants, which are transgenic plants or plants treated by genomic editing techniques.
  9. 9. An intermediate of formula II according to claim 4.

Description

Fused heterocyclic compound, preparation method thereof, weeding composition and application Technical Field The invention belongs to the technical field of pesticides, and particularly relates to a fused heterocyclic compound, a preparation method thereof, a weeding composition and application thereof. Background Weed control is a critical element in achieving efficient agriculture, and despite the diversity of herbicides on the market, the herbicidal properties of these known compounds on harmful plants and the selectivity on crops are not entirely satisfactory. And due to the continuous expansion of the market, the resistance of weeds, the service life of the drugs, the economy of the drugs and other problems and the increasing importance of people on the environment, scientists are required to continuously research and further develop new herbicide varieties with high efficiency, safety, economy and different action modes. Disclosure of Invention The invention provides a fused heterocyclic compound, a preparation method thereof, a weeding composition and application thereof, wherein the compound has excellent weeding activity and crop safety. The technical scheme adopted by the invention is as follows: A fused heterocyclic compound represented by the general formula I: Wherein X represents O or S; y represents a direct bond or CR 7R8; R 1 represents haloalkyl, R 4 represents halogen, R 6 represents cycloalkylalkyl; R 2、R3、R5、R7、R8 each independently represents hydrogen, halogen, alkyl, alkenyl, alkynyl, cyano, nitro, cycloalkyl, aryl, heterocyclyl, -OR, -SR, -SOR, - (SO 2)R、-N(R)2, -O (CO) R, -O (CO) OR, - (CO) R, OR- (CO) N (R) 2, OR R 7 and R 8 together form an alkylene group, the alkyl, alkenyl, OR alkynyl being optionally substituted with at least one group selected from halogen, cyano, nitro, cycloalkyl, aryl, heterocyclyl, -OR, -SR, -SOR, - (SO 2)R、-N(R)2, -O (CO) R, -O (CO) OR, - (CO) R, OR- (CO) N (R) 2; The foregoing "cycloalkyl", "heterocyclyl" OR "aryl" is optionally substituted with at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, -OR, -SR, - (CO) R, - (CO) OR, - (CO) N (R) 2、-(CS)N(R)2, - (SO) R OR- (SO 2) R; r independently represents hydrogen, alkyl, alkenyl, alkynyl, alkyl, alkenyl or alkynyl substituted by at least one group selected from halogen, hydroxy, alkoxy, cyano or alkoxycarbonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy. In one embodiment, R 1 represents a halogenated C1-C8 alkyl group, R 6 represents a C3-C8 cycloalkyl C1-C8 alkyl group; R 2、R3、R5、R7、R8 each independently represents hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, cyano, nitro, C3-C8 cycloalkyl, aryl, heterocyclyl, -OR, -SR, -SOR, - (SO 2)R、-N(R)2, -O (CO) R, -O (CO) OR, - (CO) R, OR- (CO) N (R) 2, OR R 7 and R 8 together form C1-C8 alkylene, the C1-C8 alkyl, C2-C8 alkenyl, OR C2-C8 alkynyl being optionally substituted with at least one group selected from halogen, cyano, nitro, C3-C8 cycloalkyl, aryl, heterocyclyl, -OR, -SR, -SOR, - (SO 2)R、-N(R)2, -O (CO) R, -O (CO) OR, - (CO) R, OR- (CO) N (R) 2; The foregoing "C3-C8 cycloalkyl", "heterocyclyl" OR "aryl" is optionally substituted with at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, haloC 1-C8 alkyl, haloC 2-C8 alkenyl, haloC 2-C8 alkynyl, -OR, -SR, - (CO) R, - (CO) OR, - (CO) N (R) 2、-(CS)N(R)2, - (SO) R OR- (SO 2) R; R independently of one another represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkyl substituted by at least one radical selected from halogen, hydroxy, C1-C8 alkoxy, cyano or C1-C8 alkoxycarbonyl, C2-C8 alkenyl or C2-C8 alkynyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl C1-C8 alkyl, phenyl or phenyl substituted by at least one radical selected from halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halogenated C1-C8 alkoxy. In another embodiment, R 1 represents a halogenated C1-C6 alkyl group, R 6 represents a C3-C6 cycloalkyl C1-C6 alkyl group; R 2、R3、R5、R7、R8 each independently represents hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cyano, nitro, C3-C6 cycloalkyl, aryl, heterocyclyl, -OR, -SR, -SOR, - (SO 2)R、-N(R)2, -O (CO) R, -O (CO) OR, - (CO) R, OR- (CO) N (R) 2, OR R 7 and R 8 together form C1-C6 alkylene, the C1-C6 alkyl, C2-C6 alkenyl, OR C2-C6 alkynyl being optionally substituted with at least one group selected from halogen, cyano, nitro, C3-C6 cycloalkyl, aryl, heterocyclyl, -OR, -SR, -SOR, - (SO 2)R、-N(R)2, -O (CO) R, -O (CO) OR, - (CO) R, OR- (CO) N (R) 2; the foregoing "C3-C6 cycloalkyl", "heterocyclyl" OR "aryl" is optionally substituted wit