An aryl isoxazoline compound and its use

Abstract

The present invention belongs to the field of agricultural herbicides, and particularly relates to an arylisoxazoline compound and its use. The arylisoxazoline compound is shown as general formula (I). The compound of general formula (I) has good herbicidal activity, can effectively control gramineous and broad-leaved weeds, can obtain good herbicidal effects at low doses, and has good safety for crops such as corn, wheat, soybeans, etc., and can be used as a herbicide in agriculture.

Description

Technical Field

[0001] The present invention belongs to the field of agricultural herbicides, and particularly relates to an arylisoxazoline compound and its use. Background Art

[0002] There are many patent reports on the research of arylisoxazoline compounds as herbicides. For example, the following general formula compounds disclosed in CN105753853 have good control effects on various broadleaf and gramineous weeds.

[0003]

[0004] In the prior art, although the disclosed compounds have certain similarities with the compounds of the present invention, the present invention introduces groups on the isoxazoline ring, making its structure significantly different from that in the prior art. And those skilled in the art know that the changes in chemical structure and substituents cannot be analogized and predicted in terms of whether they can bring active effects. Summary of the Invention

[0005] In order to develop new herbicides to solve the increasingly serious herbicide resistance problem, the present invention provides an arylisoxazoline compound and its use.

[0006] To achieve the above object, the technical solution adopted by the present invention is as follows:

[0007] An arylisoxazoline compound is shown in the general formula (I):

[0008]

[0009] In the formula:

[0010] R 1 、R 2 are each independently selected from hydrogen, halogen, or C 1 -C 6 alkyl;

[0011] R 3 is selected from hydrogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, phenyl, or phenyl substituted by 1-4 groups independently selected from the following: 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;

[0012] R 4 selected from hydrogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, CO 2 R 7 or CH 2 OR 8 ;

[0013] R 5 selected from hydrogen, cyano, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 epoxyalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarbonylC 1 -C 6 alkyl, C 1 -C 6 alkylaminoC 1 -C 6 alkyl, di(C 1 -C 6 alkylaminoC 1 -C 6 alkyl, C 1 -C 6 alkylthioC 1 -C 6 alkyl, C 1 -C 6 alkylCO 2 R 7, CO 2 R 7 , CH 2 OR 8 , CONR 9 R 10 , aryl, heteroaryl, arylC 1 -C 3 -alkyl or heteroarylC 1 -C 3 -alkyl, the following groups being: 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;

[0014] R 6 is selected from hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -epoxyalkyl, C 3 -C 6 -cycloalkylmethylene, C 3 -C 6 -epoxyalkylmethylene, C 1 -C 6 -alkylCO 2 R 7 , CO 2 R 7 , COR 7 , CH 2 OR 8 , (CH 2 ) n NR 9 R 10 , CONR 9 R 10 , C 1 -C 6 -alkoxyC 1 -C 6 -alkyl,1 -C 6 Alkyl carbonyl C 1 -C 6 Alkyl, aryl, heteroaryl, arylmethyl or heteroarylmethyl, unsubstituted or substituted by 1-4 groups independently selected from the following groups: halogen, CN, NO 2 、C 1 -C 6 Alkyl, C 1 -C 6 Halogenated alkyl, C 1 -C 6 Alkoxy, C 1 -C 6 Halogenated alkoxy, C 1 -C 6 Alkoxycarbonyl, C 1 -C 6 Alkylthio or C 1 -C 6 Alkylsulfonyl;

[0015] n is selected from 1, 2 or 3;

[0016] R 3 、R 5 can be connected to the adjacent C to form a five-membered or six-membered ring;

[0017] R 7 is selected from hydrogen, C 1 -C 6 Alkyl, C 1 -C 6 Halogenated alkyl, 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 or C 2 -C 6 Alkenylcarbonyloxy C 2 -C 4 Alkyl, phenyl, benzyl, furanmethyl, thiazolylmethyl, tetrahydrofuranmethyl or pyridylmethyl, unsubstituted or substituted by 1-4 groups independently selected from the following groups: halogen, CN, NO 2 、C 1 -C 6 Alkyl, C1 -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;

[0018] R 8 selected from 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 alkylaminosulfonyl, bis(C 1 -C 6 )alkylaminosulfonyl, C 1 -C 6 alkylaminocarbonyl, bis(C 1 -C 6 )alkylaminocarbonyl, bis(C 1 -C 6 )alkylaminothiocarbonyl, C 1 -C 6 alkylthio C 1 -C 6 alkylcarbonyl, phenyl, phenyl C which is unsubstituted or substituted by 1 - 4 groups independently selected from the following groups 1 -C 2 alkyl, phenyl C 2 -C 4 alkenyl, phenylcarbonyl, phenyl C 1 -C 2 alkylcarbonyl, phenoxy C 1 -C 2 alkylcarbonyl, phenyl C2 -C 4 Alkenyl carbonyl, heteroaryl, 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 Halogenated alkyl, C 1 -C 6 Alkoxy, C 1 -C 6 Halogenated alkoxy, C 1 -C 6 Alkoxycarbonyl, C 1 -C 6 Alkylthio or C 1 -C 6 Alkylsulfonyl;

[0019] R 9 、R 10 Are each independently selected from hydrogen, C 1 -C 6 Alkyl, C 1 -C 6 Halogenated alkyl, 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); or, R 9 、R 10 May be linked through N to form a five - or six - membered ring;

[0020] Q is selected from any one of the following Q1 - Q3;

[0021]

[0022] R 11 Is selected from C 1 -C 6 Alkyl or C 1 -C 6 Halogenated alkyl;

[0023] R 12 Is selected from C 1 -C 6 Alkyl, C 1 -C6 haloalkyl or NH 2 ;

[0024] R 13 is selected from hydrogen or C 1 -C 6 alkyl;

[0025] R 14 is selected from C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or NH 2 ;

[0026] X is selected from C or N;

[0027] Y is selected from O or S;

[0028] R 3 、R 4 When R and R are selected from different substituents, the carbon atom to which they are attached is an asymmetric carbon atom, and its configuration is R or S;

[0029] R 5 and OR 6 When the carbon atoms to which they are attached are asymmetric carbon atoms, their configurations are R or S;

[0030] or, an agriculturally usable salt or derivative of the compound represented by formula (I) or an optically active isomer of the compound represented by formula (I).

[0031] A more preferred compound of the present invention is: in general formula (I)

[0032] R 1 、R 2 are respectively selected from hydrogen, halogen or C 1 -C 4 alkyl;

[0033] R 3 is selected from hydrogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, phenyl or phenyl substituted by 1-4 groups independently selected from the following: halogen, CN, NO 2 、C 1 -C 4 alkyl, C1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylthio or C 1 -C 4 alkylsulfonyl;

[0034] R 4 is selected from hydrogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, CO 2 R 7 or CH 2 OR 8 ;

[0035] R 5 is selected from hydrogen, cyano, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 epoxyalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxyC 1 -C 4 alkyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkylcarbonylC 1 -C 4 alkyl, C 1 -C 4 alkylaminoC 1 -C 4 alkyl, di(C 1 -C 4 )alkylaminoC 1 -C 4 alkyl, C 1 -C 4 alkylthioC 1 -C 4 alkyl, C 1 -C4 alkyl CO 2 R 7 、CO 2 R 7 、CH 2 OR 8 、CONR 9 R 10 , aryl, heteroaryl, arylC 1 -C 3 alkyl or heteroarylC 1 -C 3 alkyl, the following groups being: 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 or C 1 -C 4 alkylsulfonyl;

[0036] R 6 selected from hydrogen, C 1 -C 4 alkyl、C 1 -C 4 haloalkyl、C 3 -C 6 cycloalkyl、C 3 -C 6 epoxyalkyl、C 3 -C 6 cycloalkylmethylene、C 3 -C 6 epoxyalkylmethylene、C 1 -C 4 alkyl CO 2 R 7 、CO 2 R 7 、COR 7 、CH 2 OR 8 、(CH 2 ) n NR 9 R 10 、CONR 9 R 10 、C 1 -C4 Alkoxy C 1 -C 4 Alkyl, C 1 -C 4 Alkylcarbonyl C 1 -C 4 Alkyl, phenyl, benzyl, pyridyl, pyridinemethylene, furyl or furylmethylene which is unsubstituted or substituted by 1 - 4 groups independently selected from the following groups: halogen, CN, NO 2 、C 1 -C 4 Alkyl, C 1 -C 4 Halogenated alkyl, C 1 -C 4 Alkoxy or C 1 -C 4 Halogenated alkoxy;

[0037] n is selected from 1, 2 or 3;

[0038] R 3 、R 5 may be connected to the adjacent C to form a five - membered or six - membered ring;

[0039] R 7 is selected from hydrogen, C 1 -C 4 Alkyl, C 1 -C 4 Halogenated alkyl, 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 Alkenylcarbonyloxy C 2 -C 4 Alkyl, phenyl, benzyl, furylmethylene, thiazolylmethylene, tetrahydrofurylmethylene or pyridinemethylene which is unsubstituted or substituted by 1 - 4 groups independently selected from the following groups: halogen, CN, NO 2 、C 1 -C 4 Alkyl, C 1 -C 4 Halogenated alkyl, C 1 -C4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkoxycarbonyl;

[0040] R 8 selected from 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 alkylaminosulfonyl, bis(C 1 -C 4 )alkylaminosulfonyl, C 1 -C 4 alkylaminocarbonyl, bis(C 1 -C 4 )alkylaminocarbonyl, bis(C 1 -C 4 )alkylaminothiocarbonyl, C 1 -C 4 alkylthio C 2 -C 4 alkylcarbonyl, phenyl, phenyl C 1 -C 2 alkyl, phenyl C 2 -C 4 alkenyl, phenylcarbonyl, phenyl C 1 -C 2 alkylcarbonyl, phenoxy C 1 -C 2 alkylcarbonyl, phenyl C 2 -C 4 alkenylcarbonyl, heteroaryl, heteroaryl C 1 -C 2 alkyl, heteroarylcarbonyl, the following groups being: halogen, CN, NO 2 、C 1 -C4 Alkyl, C 1 -C 4 Halogenated alkyl, C 1 -C 4 Alkoxy, C 1 -C 4 Halogenated alkoxy, C 1 -C 4 Alkoxycarbonyl, C 1 -C 4 Alkylthio or C 1 -C 4 Alkylsulfonyl;

[0041] R 9 、R 10 Are each independently selected from hydrogen, C 1 -C 4 Alkyl, C 1 -C 4 Halogenated alkyl, 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); or, R 9 、R 10 May be joined through N to form a five- or six-membered ring;

[0042] Q is selected from Q1, Q2 or Q3;

[0043] R 11 Is selected from C 1 -C 4 Alkyl or C 1 -C 4 Halogenated alkyl;

[0044] R 12 Is selected from C 1 -C 4 Alkyl, C 1 -C 4 Halogenated alkyl or NH 2 ;

[0045] R 13 Is selected from hydrogen or C 1 -C 4 Alkyl;

[0046] R 14 Is selected from C 1 -C4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or NH 2 ;

[0047] X is selected from C or N;

[0048] Y is selected from O or S;

[0049] R 3 and R 4 When selected from different substituents, the carbon atom to which they are attached is an asymmetric carbon atom, and its configuration is R or S;

[0050] R 5 and OR 6 When they are different, the carbon atom to which they are attached is an asymmetric carbon atom, and its configuration is R or S;

[0051] Or, the compound represented by formula (I), the agriculturally usable salts or derivatives of the optical isomers of the compound represented by formula (I).

[0052] The more preferred compounds of the present invention are: in general formula (I)

[0053] R 1 and R 2 are respectively selected from hydrogen, halogen, methyl, ethyl, propyl or isopropyl;

[0054] R 3 is selected from hydrogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, phenyl or phenyl substituted by 1-2 substituents 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 or difluoroethoxy;

[0055] R 4 is selected from hydrogen, cyano, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

[0056] R 5Selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, chloromethyl, fluoromethyl, iodomethyl, trifluoromethyl, difluoromethyl, trifluoroethyl, difluoroethoxy, difluoromethoxy, trifluoroethoxy, cyclopropyl, cyclohexyl, cyclopentyl, epoxypropyl, C 1 -C 4 alkoxy C 1 -C 3 alkyl, C 1 -C 4 alkylcarbonyl C 1 -C 2 alkyl, C 1 -C 4 alkylthio C 1 -C 2 alkyl, C 1 -C 2 alkyl CO 2 R 7 、CO 2 R 7 、CH 2 OR 8 、CONR 9 R 10 、phenyl or benzyl which is unsubstituted or substituted by 1-2 groups 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 or difluoroethoxy;

[0057] R 6 Selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclopentyl, cyclohexyl, epoxyethyl, epoxypropyl, cyclopropylmethylene, cyclopentylmethylene, cyclohexylmethylene, chloromethyl, fluoromethyl, iodomethyl, trifluoromethyl, difluoromethyl, difluoroethyl, trifluoroethyl, 1-chloroethyl, 1-fluoroethyl, 1-chloropropyl, 1-fluoropropyl, CH 2 CO 2 R 7 、CH(CH 3 )CO 2 R 7 、CH 2 CH 2 CO 2 R 7 、CO 2 R 7 、COR 7 、CH 2 OR 8 、(CH 2 ) nNR 9 R 10 、CONR 9 R 10 、、C 1 -C 3 alkoxy C 1 -C 3 alkyl, C 1 -C 4 alkylcarbonyl C 1 -C 2 alkyl, phenyl, benzyl, furyl or furylmethylene which is unsubstituted or substituted by 1 - 2 groups 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 or difluoroethoxy;

[0058] n is selected from 1, 2 or 3;

[0059] R 3 、R 5 may be connected to the adjacent C to form a five - membered or six - membered ring;

[0060] 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, phenyl, benzyl, furylmethylene or tetrahydrofurylmethylene which is unsubstituted or substituted by 1 - 4 groups independently selected from the following groups: fluorine, chlorine, bromine, CN, NO 2 、methyl, ethyl, isopropyl, tert - butyl, trifluoromethyl, methoxy, ethoxy, tert - butoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy or difluoroethoxy;

[0061] R 8 is selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylcarbonyl, C1 -C 4 Halogenated alkyl carbonyl, C 3 -C 6 Cycloalkyl carbonyl, C 3 -C 6 Halogenated cycloalkyl carbonyl, C 1 -C 4 Alkylsulfonyl, C 1 -C 4 Halogenated alkylsulfonyl, C 1 -C 3 Alkylaminosulfonyl, bis(C 1 -C 3 )alkylaminosulfonyl, C 1 -C 3 Alkylaminocarbonyl, bis(C 1 -C 3 )alkylaminocarbonyl, bis(C 1 -C 3 )alkylaminothiocarbonyl, C 1 -C 2 Alkylthio C 2 -C 4 Alkyl carbonyl, phenyl C which is unsubstituted or substituted by 1-4 groups independently selected from the following groups 1 -C 2 Alkyl, phenylcarbonyl, phenyl C 1 -C 2 Alkyl carbonyl, phenyl C 2 -C 4 Alkenyl carbonyl, phenoxy C 1 -C 2 Alkyl carbonyl, thiophenecarbonyl, pyrazolecarbonyl, quinolinecarbonyl, the following groups are: halogen, CN, NO 2 、C 1 -C 4 Alkyl, C 1 -C 4 Halogenated alkyl, C 1 -C 4 Alkoxy, C 1 -C 4 Halogenated alkoxy, C 1 -C 4 Alkoxycarbonyl, C 1 -C 4 Alkylthio or C 1 -C 4 Alkylsulfonyl;

[0062] R 9 、R 10 Are each independently selected from hydrogen, C 1 -C 4 Alkyl, C 1 -C4 haloalkyl, C 1 -C 4 alkoxycarbonyl C 1 -C 3 alkyl, SO 2 NH(C 1 -C 4 alkyl) or SO 2 N(C 1 -C 4 alkyl)(C 1 -C 4 alkyl);

[0063] Q is selected from Q1, Q2 or Q3;

[0064] R 11 is selected from C 1 -C 4 haloalkyl;

[0065] R 12 is selected from C 1 -C 4 alkyl or NH 2 ;

[0066] R 13 is selected from hydrogen or C 1 -C 4 alkyl;

[0067] R 14 is selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, allyl, propargyl or NH 2 ;

[0068] X is selected from C or N;

[0069] Y is selected from O or S;

[0070] R 3 , R 4 When R and R are selected from different substituents, the carbon atom to which they are attached is an asymmetric carbon atom, and its configuration is R or S;

[0071] R 5 and OR 6 When they are different, the carbon atom to which they are attached is an asymmetric carbon atom, and its configuration is R or S;

[0072] or, the compound represented by formula (I), the agriculturally usable salts or derivatives of the optical isomers of the compound represented by formula (I).

[0073] A more preferred compound of the present invention is: in the general formula (I)

[0074] R1 , R 2 is independently selected from hydrogen, fluorine, chlorine, bromine or methyl;

[0075] R 3 is selected from hydrogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, trifluoromethyl, difluoromethyl, difluoromethoxy, trifluoromethoxy, trifluoroethoxy, difluoroethoxy, phenyl or phenyl substituted by 1-2 groups independently selected from: fluorine, chlorine, bromine, methoxy or methyl;

[0076] R 4 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl or trifluoroethyl;

[0077] R 5 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, chloromethyl, fluoromethyl, iodomethyl, trifluoromethyl, difluoromethyl, trifluoroethyl, difluoroethoxy, difluoromethoxy, trifluoroethoxy, cyclopropyl, cyclohexyl, cyclopentyl, epoxypropyl, C 1 -C 4 alkoxy C 1 -C 3 alkyl, C 1 -C 3 alkylcarbonyl C 1 -C 2 alkyl, C 1 -C 2 alkylthio C 1 -C 2 alkyl, 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 , phenyl or benzyl which is unsubstituted or substituted by 1-2 groups independently selected from: fluorine, chlorine, bromine, CN, NO 2 , methyl, isopropyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy;

[0078] R 6Selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclopentyl, cyclohexyl, epoxyethyl, epoxypropyl, cyclopropylmethylene, cyclopentylmethylene, cyclohexylmethylene, difluoromethyl, difluoroethyl, trifluoroethyl, 1-chloroethyl, 1-fluoroethyl, 1-chloropropyl, 1-fluoropropyl, CH 2 CO 2 R 7 、CH(CH 3 )CO 2 R 7 、CH 2 CH 2 CO 2 R 7 、CO 2 R 7 、COR 7 、CH 2 OR 8 、(CH 2 ) n NR 9 R 10 、CONR 9 R 10 、phenyl, benzyl or furanylmethylene which is unsubstituted or substituted by 1-2 groups independently selected from the following: fluorine, chlorine, bromine, CN, NO 2 、methyl, isopropyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy;

[0079] n is selected from 1, 2 or 3;

[0080] R 3 、R 5 may be connected to the adjacent C to form cyclopentane or cyclohexane;

[0081] 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 2 alkyl, phenyl, benzyl, furanylmethylene or tetrahydrofuranylmethylene which is unsubstituted or substituted by 1-4 groups independently selected from the following: fluorine, chlorine, bromine, CN, methyl or methoxy;

[0082] R 8 is selected from C 1 -C 4 alkyl, C 1 -C4 Halogenated alkyl, C 1 -C 4 Alkoxycarbonyl, C 1 -C 4 Alkylcarbonyl, C 1 -C 4 Halogenated alkylcarbonyl, C 3 -C 6 Cycloalkylcarbonyl, C 3 -C 6 Halogenated cycloalkylcarbonyl, C 1 -C 4 Alkylsulfonyl, C 1 -C 4 Halogenated alkylsulfonyl, C 1 -C 2 Alkylthio C 2 -C 4 Alkylcarbonyl, unsubstituted or substituted by 1 - 3 phenylcarbonyl, phenylacetyl, phenylpropionyl, phenoxy C 1 -C 2 Alkylcarbonyl or quinolinecarbonyl: fluorine, chlorine, bromine, CN, NO 2 、C 1 -C 4 Alkyl, C 1 -C 4 Halogenated alkyl, C 1 -C 4 Alkoxy, C 1 -C 4 Halogenated alkoxy, C 1 -C 4 Alkylthio or C 1 -C 4 Alkylsulfonyl;

[0083] R 9 、R 10 Are each independently selected from hydrogen, C 1 -C 4 Alkyl, C 1 -C 4 Halogenated alkyl or C 1 -C 3 Alkoxycarbonyl C 1 -C 2 Alkyl;

[0084] Q is selected from Q1, Q2 or Q3;

[0085] When Q is selected from Q2, R 5 Is not selected from CO 2 R 7 、CH 2 OR 8 Or CONR 9 R10 ;

[0086] R 11 is selected from difluoromethyl, trifluoromethyl, trifluoroethyl or difluoroethyl;

[0087] R 12 is selected from methyl, ethyl, n-propyl, isopropyl, tert-butyl or NH 2 ;

[0088] R 13 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl;

[0089] R 14 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, allyl, propargyl or NH 2 ;

[0090] X is selected from C or N;

[0091] Y is selected from O or S;

[0092] R 3 R 4 When R and R are selected from different substituents, the carbon atom to which they are attached is an asymmetric carbon atom, and its configuration is R or S;

[0093] R 5 and OR 6 When they are different, the carbon atom to which they are attached is an asymmetric carbon atom, and its configuration is R or S;

[0094] or an agriculturally usable salt or derivative of the compound represented by formula (I) or an optically active isomer of the compound represented by formula (I).

[0095] A more preferred compound of the present invention is: in general formula (I)

[0096] R 1 R 2 are respectively selected from hydrogen, fluorine, chlorine, bromine or methyl;

[0097] R 3 is selected from hydrogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy;

[0098] R 4 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl or tert-butyl;

[0099] R 5Selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, chloromethyl, fluoromethyl, iodomethyl, trifluoromethyl, difluoromethyl, trifluoroethyl, cyclopropyl, cyclohexyl, cyclopentyl, glycidyl, C 1 -C 3 alkoxy C 1 -C 2 alkyl, C 1 -C 3 alkylcarbonyl C 1 -C 2 alkyl, C 1 -C 2 alkylthio C 1 -C 2 alkyl, 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 、phenyl or benzyl which is unsubstituted or substituted by 1-2 groups independently selected from the following: fluorine, chlorine, bromine, CN, NO 2 、methyl, isopropyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy;

[0100] R 6 Selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclopentyl, cyclohexyl, epoxyethyl, glycidyl, cyclopropylmethylene, cyclopentylmethylene, cyclohexylmethylene, difluoromethyl, difluoroethyl, trifluoroethyl, 1-chloroethyl, 1-fluoroethyl, 1-chloropropyl, 1-fluoropropyl, 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 、CH(CH 3 )CO 2 CH 3 、CH(CH3 )CO 2 C 2 H 5 、CH 2 CO 2 CH(CH 3 ) 2 、CH 2 CH 2 CO 2 CH(CH 3 ) 2 、CH(CH 3 )CO 2 CH(CH 3 ) 2 、CO 2 C 2 H 5 、CO 2 CH 3 、CO 2 C 2 H 5 、CO 2 CH(CH 3 ) 2 、COR 7 、CH 2 OR 8 、CH 2 CH 2 NR 9 R 10 、CH 2 NR 9 R 10 、CONR 9 R 10 、phenyl or benzyl which is unsubstituted or substituted by 1 or 2 groups independently selected from: fluorine, chlorine or bromine;

[0101] R 3 、R 5 may be connected to the adjacent C to form cyclopentane or cyclohexane;

[0102] R 7 selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, sec-butyl, tert-butyl, trifluoroethyl, difluoroethyl, 1-chloroethyl, 1-fluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl, allyl, propargyl, methoxyethyl, ethoxyethyl, methoxymethyl, ethoxymethyl, phenyl or benzyl which is unsubstituted or substituted by 1 or 2 groups independently selected from: fluorine, chlorine or bromine;

[0103] R 8Selected from methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, sec-butyl, tert-butyl, trifluoroethyl, difluoroethyl, 1-chloroethyl, 1-fluoroethyl, methoxyacetyl, ethoxyacetyl, isopropoxyacetyl, acetyl, n-propionyl, n-butyryl, isopropionyl, isobutyryl, sec-butyryl, tert-butyryl, trifluoroacetyl, difluoroacetyl, trifluoromethylcarbonyl, difluoromethylcarbonyl, chloroacetyl, fluoroacetyl, 2-chloropropionyl, 3-chloropropionyl, cyclopropylcarbonyl, 1-chlorocyclopropylcarbonyl, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, 3-chloropropylsulfonyl, 3-methylthiopropionyl, phenylcarbonyl, phenylacetyl, phenylpropionyl, phenoxyC which is unsubstituted or substituted by 1-3 groups independently selected from the following groups 1 -C 2 alkylcarbonyl or quinolinecarbonyl: fluorine, chlorine, bromine or methyl;

[0104] R 9 Selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, sec-butyl, tert-butyl, trifluoroethyl, difluoroethyl, 1-chloroethyl or 1-fluoroethyl;

[0105] R 10 Selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, sec-butyl, tert-butyl, 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 、CH(CH 3 )CO 2 CH 3 、CH(CH 3 )CO 2 C 2 H 5 、CH 2 CO 2 CH(CH 3 ) 2 、CH 2 CH 2 CO 2 CH(CH 3 ) 2 or CH(CH 3 )CO 2CH(CH 3 ) 2 ;

[0106] Q is selected from Q1, Q2 or Q3;

[0107] When Q is selected from Q2, R 5 is not selected from CO 2 R 7 , CH 2 OR 8 , CONR 9 R 10 ;

[0108] R 11 is selected from trifluoromethyl;

[0109] R 12 is selected from methyl or NH 2 ;

[0110] R 13 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl;

[0111] R 14 is selected from methyl, ethyl, propenyl, propynyl or NH 2 ;

[0112] X is selected from C or N;

[0113] Y is selected from O or S;

[0114] R 3 , R 4 When the connected carbon atoms are asymmetric carbon atoms with different substituents, their configurations are R or S;

[0115] R 5 and OR 6 When they are not connected at the same time, the connected carbon atoms are asymmetric carbon atoms with configurations of R or S;

[0116] Or, the compound represented by formula (I), the agriculturally available salts or derivatives of the optically active isomers of the compound represented by formula (I).

[0117] A more preferred compound of the present invention is: in general formula (I)

[0118] R 1 , R 2 are respectively selected from hydrogen, fluorine, chlorine, bromine or methyl;

[0119] R 3 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, isopropoxy or tert-butoxy;

[0120] R4 selected from hydrogen, methyl, ethyl, n-propyl, isopropyl or tert-butyl;

[0121] R 5 selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, chloromethyl, fluoromethyl, iodomethyl, trifluoromethyl, difluoromethyl, trifluoroethyl, cyclopropyl, cyclohexyl, cyclopentyl, epoxypropyl, CH 2 OCH 3 、CH 2 OC 2 H 5 、CH 2 CH 2 OCH 3 、CH 2 CH 2 OC 2 H 5 、CH(CH 3 )OCH 3 、CH(CH 3 )OC 2 H 5 、CH 2 OCH(CH 3 ) 2 、CH 2 CH 2 OCH(CH 3 ) 2 、CH(CH 3 )OCH(CH 3 ) 2 、CH 2 COCH 3 、CH 2 COC 2 H 5 、CH 2 CH 2 COCH 3 、CH 2 CH 2 COC 2 H 5 、CH(CH 3 )COCH 3 、CH(CH 3 )COC 2 H 5 、CH 2 COCH(CH 3 ) 2 、CH 2 CH 2 COCH(CH 3 ) 2 or CH(CH 3)COCH(CH 3 ) 2 、CH 2 SCH 3 、CH 2 SC 2 H 5 、CH 2 CH 2 SCH 3 、CH 2 CH 2 SC 2 H 5 、CH(CH 3 )SCH 3 、CH(CH 3 )SC 2 H 5 、CH 2 SCH(CH 3 ) 2 、CH 2 CH 2 SCH(CH 3 ) 2 、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 、CH 2 CO 2 CH(CH 3 ) 2 、CH 2 CH 2 CO 2 CH(CH 3 ) 2 、CO 2 R 7 、CH 2 OR 8 、CONR 9 R 10 、phenyl or benzyl which is unsubstituted or substituted by 1 - 2 groups independently selected from the following: fluorine, chlorine or bromine;

[0122] R 6Selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclopentyl, cyclohexyl, epoxyethyl, epoxypropyl, cyclopropylmethylene, cyclopentylmethylene, cyclohexylmethylene, difluoromethyl, difluoroethyl, trifluoroethyl, 1-chloroethyl, 1-fluoroethyl, 1-chloropropyl, 1-fluoropropyl, 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 、CH(CH 3 )CO 2 CH 3 、CH(CH 3 )CO 2 C 2 H 5 、CH 2 CO 2 CH(CH 3 ) 2 、CH 2 CH 2 CO 2 CH(CH 3 ) 2 、CH(CH 3 )CO 2 CH(CH 3 ) 2 、CO 2 C 2 H 5 、CO 2 CH 3 、CO 2 C 2 H 5 、CO 2 CH(CH 3 ) 2 、COR 7 、CH 2 OCH 3 、CH 2 OC 2 H 5 、CH 2 OCH(CH 3 ) 2 、CH 2CH 2 N(CH 3 ) 2 、CH 2 N(CH 3 ) 2 、CON(CH 3 ) 2 ;

[0123] R 7 is selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, sec-butyl, tert-butyl, trifluoroethyl, difluoroethyl, 1-chloroethyl, 1-fluoroethyl, methoxyethyl, ethoxyethyl, methoxymethyl or ethoxymethyl;

[0124] R 8 is selected from methoxyacetyl, ethoxyacetyl, isopropoxyacetyl, acetyl, n-propionyl, n-butyryl, isopropionyl, isobutyryl, sec-butyryl, tert-butyryl, trifluoroacetyl, difluoroacetyl, trifluoromethylcarbonyl, difluoromethylcarbonyl, chloroacetyl, fluoroacetyl, 2-chloropropionyl, 3-chloropropionyl, cyclopropanecarbonyl, 1-chlorocyclopropanecarbonyl, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, 3-chloropropylsulfonyl or 3-methylthiopropionyl;

[0125] R 9 is selected from hydrogen, methyl, ethyl or n-propyl;

[0126] R 10 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, 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 、CH(CH 3 )CO 2 CH 3 、CH(CH 3 )CO 2 C 2 H 5 、CH 2 CO 2 CH(CH 3 ) 2 、CH 2 CH2 CO 2 CH(CH 3 ) 2 or CH(CH 3 )CO 2 CH(CH 3 ) 2 ;

[0127] Q is selected from Q1, Q2 or Q3;

[0128] When Q is selected from Q2, R 5 is not selected from CO 2 R 7 , CH 2 OR 8 , CONR 9 R 10 ;

[0129] R 11 is selected from trifluoromethyl;

[0130] R 12 is selected from methyl or NH 2 ;

[0131] R 13 is selected from methyl, ethyl, n-propyl or isopropyl;

[0132] R 14 is selected from methyl, ethyl, propenyl, propynyl or NH 2 ;

[0133] X is selected from C or N;

[0134] Y is selected from O or S;

[0135] R 3 、R 4 When R and R are selected from different substituents, the carbon atom to which they are attached is an asymmetric carbon atom, and its configuration is R or S;

[0136] R 5 and OR 6 When they are different, the carbon atom to which they are attached is an asymmetric carbon atom, and its configuration is R or S;

[0137] or an agriculturally usable salt or derivative of the compound represented by formula (I) or the optical isomer of the compound represented by formula (I).

[0138] A more preferred compound of the present invention is: in general formula (I)

[0139] R 1 、R 2 are respectively selected from hydrogen, fluorine, chlorine, bromine or methyl;

[0140] R 3Selected from hydrogen, methyl or methoxy;

[0141] R 4 Selected from hydrogen or methyl;

[0142] R 5 Selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclohexyl or cyclopentyl;

[0143] R 6 Selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclopentyl, cyclohexyl, epoxyethyl, epoxypropyl, cyclopropylmethylene, cyclopentylmethylene, cyclohexylmethylene, difluoromethyl, difluoroethyl, trifluoroethyl, 1-chloroethyl, 1-fluoroethyl, 1-chloropropyl, 1-fluoropropyl, 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 、CH(CH 3 )CO 2 CH 3 、CH(CH 3 )CO 2 C 2 H 5 、CH 2 CO 2 CH(CH 3 ) 2 、CH 2 CH 2 CO 2 CH(CH 3 ) 2 、CH(CH 3 )CO 2 CH(CH 3 ) 2 、CO 2 C 2 H 5 、CO 2 CH 3 、CO 2 C 2 H 5 、CO 2 CH(CH3 ) 2 , COR 7 , CH 2 OCH 3 , CH 2 OC 2 H 5 , CH 2 OCH(CH 3 ) 2 , CH 2 CH 2 N(CH 3 ) 2 , CH 2 N(CH 3 ) 2 、CON(CH 3 ) 2 ;

[0144] R 7 is selected from methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, sec-butyl, tert-butyl, trifluoroethyl, difluoroethyl, 1-chloroethyl, 1-fluoroethyl, methoxymethyl or ethoxymethyl;

[0145] Q is selected from Q1, Q2 or Q3;

[0146] R 11 Selected from trifluoromethyl;

[0147] R 12 Selected from methyl or NH 2 ;

[0148] R 13 Selected from methyl;

[0149] R 14 Selected from methyl, propenyl, propynyl or NH 2 ;

[0150] X is selected from C or N;

[0151] Y is selected from O or S;

[0152] R 5 OR 6 The carbon atoms that are not connected at the same time are asymmetric carbon atoms, and their configuration is R or S;

[0153] Or, the compound represented by formula (I), an agriculturally acceptable salt or derivative of an optical isomer of the compound represented by formula (I).

[0154] In the definition of compounds of general formula (I) given above, the terms used are generally defined as follows:

[0155] Halogen: refers to fluorine, chlorine, bromine or iodine. Alkyl: straight-chain or branched-chain alkyl groups, such as methyl, ethyl, propyl, isopropyl, n-butyl or tert-butyl. Cycloalkyl: substituted or unsubstituted cyclic alkyl groups, such as cyclopropyl, cyclopentyl or cyclohexyl. Substituents such as methyl, halogen, etc. Haloalkyl: straight-chain or branched-chain alkyl groups in which the hydrogen atoms on these alkyl groups can be partially or completely replaced by halogen atoms, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, etc. Alkoxy: straight-chain or branched-chain alkyl groups bonded to the structure via an oxygen atom. Haloalkoxy: straight-chain or branched-chain alkoxy groups in which the hydrogen atoms on these alkoxy groups can be partially or completely replaced by halogen atoms. For example, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy, etc. Alkylthio: straight-chain or branched-chain alkyl groups bonded to the structure via a sulfur atom. Haloalkylthio: straight-chain or branched-chain alkylthio groups in which 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, etc. Alkenyl: straight-chain or branched-chain alkenes, such as vinyl, 1-propenyl, 2-propenyl and different butenyl, pentenyl and hexenyl isomers. Alkenyl also includes polyenes, such as 1,2-propadienyl and 2,4-hexadienyl. Alkylsulfonyl: straight-chain or branched-chain alkyl groups are connected to the structure via a sulfonyl group (-SO 2 -), such as methylsulfonyl. Haloalkylsulfonyl: straight-chain or branched-chain alkylsulfonyl groups in which the hydrogen atoms on the alkyl groups can be partially or completely replaced by halogen atoms. Alkylsulfinyl: straight-chain or branched-chain alkyl groups are connected to the structure via a sulfinyl group (-SO-), such as methylsulfinyl. Haloalkylsulfinyl: straight-chain or branched-chain alkylsulfinyl groups in which the hydrogen atoms on the alkyl groups can be partially or completely replaced by halogen atoms. Alkoxycarbonyl: alkoxy groups are 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: alkyl groups are connected to the structure via a carbonyl group, such as CH 3 CO- or CH 3 CH 2CO-, etc. Haloalkylcarbonyl: The haloalkyl is connected to the structure through a carbonyl group, such as CF 3 CO- or CF 2 HCO-, etc. Cycloalkylcarbonyl: The cycloalkyl is connected to the structure through a carbonyl group, such as cyclopropylcarbonyl or cyclohexylcarbonyl, etc. Haloalkylcycloalkylcarbonyl: The haloalkylcycloalkyl is connected to the structure through a carbonyl group, such as 1-chlorocyclopropylcarbonyl, etc. Alkylaminosulfonyl: Alkyl-NH-SO 2 -, such as CH 3 NHSO 2 - or C 2 H 5 NHSO 2 - etc. 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 etc. Aryl: A polycyclic aromatic group, such as phenyl, naphthyl. Heteroaryl is a five-membered or six-membered ring containing one or more N, O, S heteroatoms. For example, furyl, pyrazolyl, thiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, etc. SO 2 NH(C 1 -C 4 Alkyl): -SO 2 NHCH 3 or -SO 2 NHC 2 H 5 etc. SO2 N(C 1 -C 2 alkyl)(C 1 -C 4 alkyl):

[0156] -SO 2 N(CH 3 ) 2 or -SO 2 N(CH 3 )[CH(CH 3 ) 2 etc.

[0157] Some compounds of the present invention can be illustrated by the specific compounds listed in Tables 1 - 8, but the present invention is not limited to these compounds.

[0158] Table 1: In general formula I, Q = Q1, R 3 = H, R 4 = H, X = CH, R 11 = CF 3 , R 12 = CH 3 , R 1 , R 2 , R 5 , R 6 See the following table for details.

[0159]

[0160] Table 1

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169] Table 2: In general formula I, Q = Q1, R 3 = H, R 4 = H, X = CH, R 11 = CF 3 , R 12=NH 2 , R 1 、R 2 、R 5 、R 6 See Table 1 for details.

[0170] Table 3: In General Formula I, Q = Q1, R 3 =H, R 4 =H, X = N, R 11 =CF 3 , R 12 =CH 3 , R 1 、R 2 、R 5 、R 6 See Table 1 for details.

[0171] Table 4: In General Formula I, Q = Q1, R 3 =H, R 4 =H, X = N, R 11 =CF 3 , R 12 =NH 2 , R 1 、R 2 、R 5 、R 6 See Table 1 for details.

[0172] Table 5: In General Formula I, Q = Q2, R 3 =H, R 4 =H, X = CH, R 13 =CH 3 , R 14 =CH 3 , R 1 、R 2 、R 5 、R 6 See Table 1 for details.

[0173] Table 6: In General Formula I, Q = Q2, R 3 =H, R 4 =H, X = N, R 13 =CH 3 , R 14 =CH 3 , R 1 、R 2 、R 5 、R 6 See Table 1 for details.

[0174] Table 7: In General Formula I, Q = Q3, R 3 =H, R 4 =H, X = CH, R 13 =CH3 , R 14 =CH 3 , R 1 , R 2 , R 5 , R 6 Specifically, see Table 1.

[0175] Table 8: In general formula I, Q = Q4, R 3 =H, R 4 =H, X = N, R 13 =CH 3 , R 14 =CH 3 , R 1 , R 2 , R 5 , R 6 Specifically, see Table 1.

[0176] The compound of general formula I of the present invention can be obtained from the oxime-based compound II by chlorination or bromination with NCS, chlorine, NBS or bromine and then reacting with an olefin-bonded ring by the methods described in the literature, such as J.Agric.Food Chem.2005,53,8639 - 8643, CN105753853, WO2006090234, etc.

[0177]

[0178] The oxime-based compound II can be obtained from the methyl intermediate VI by bromination to obtain the intermediate V, followed by hydrolysis to obtain the aldehyde-based compound IV, and then by hydroxylamine oximation by the methods described in the literature, such as US4846875, CN1402979, Chemical Reaction Engineering and Technology, 2002, 18(4), 373 - 376, Acta Chimica Sinica, 2003, 24(7), 1225 - 1230, etc.

[0179]

[0180] When Q is selected from Q1, the methyl intermediate VI-1 can be obtained from the amino compound VIII by the methods described in the literature, such as WO2009050120, US5336663, US6992044 or WO2001083459, etc. When Q is selected from Q2, the methyl intermediate VI-2 can be obtained from the amino compound VIII by the methods described in the literature, such as CN105646328, US6303783, EP985670, US4816065, etc. When Q is selected from Q3, the methyl intermediate VI-3 can be obtained from the amino compound VIII by the methods described in the literature, such as US5705644, WO2003029225, WO2010145992, WO2012080239, etc.

[0181]

[0182] Unless otherwise specified, the definitions of the groups in the reaction formula are the same as before.

[0183] Use of a compound of the general formula (I) as defined above for controlling weeds.

[0184] The compounds of the present invention can effectively control weeds such as Echinochloa crusgalli, Setaria viridis, Cyperus difformis, Cyperus serotinus, Digitaria sanguinalis, Arthraxon hispidus, Abutilon theophrasti, Zinnia elegans, Amaranthus retroflexus, Portulaca oleracea, Xanthium sibiricum, Solanum nigrum, Cassia tora, Hibiscus trionum, Glycine soja, etc., and good effects can be obtained at low doses. They have a certain degree of safety for wheat, corn, rice, and soybeans and can be used as herbicides in agriculture. Therefore, the present invention also includes the use of the compound of the general formula (I) for controlling weeds.

[0185] The present invention also provides a herbicidal composition which uses the compound of the general formula (I) as an active ingredient, and the weight percentage content of the active ingredient in the composition is 0.1 - 99%. Therefore, the present invention also includes the use of this composition for controlling weeds.

[0186] By adding one or more other herbicides to the composition, it can have a broader spectrum of activity than the compound of the general formula (I) alone. In addition, other herbicides can have a synergistic effect on the herbicidal activity of the compound of the general formula (I), or the compound of the general formula (I) can be mixed with other herbicides. The content of the active ingredient in the mixture varies within a wide range, generally 1% - 95%, and a more suitable content is 5% - 60%.

[0187] The composition using the compound of the general formula (I) of the present invention as an active ingredient can effectively control weeds. As a herbicide, this type of compound can effectively control weeds such as Echinochloa crusgalli, Setaria viridis, Cyperus difformis, Cyperus serotinus, Digitaria sanguinalis, Arthraxon hispidus, Abutilon theophrasti, Zinnia elegans, Amaranthus retroflexus, Portulaca oleracea, Xanthium sibiricum, Solanum nigrum, Cassia tora, Hibiscus trionum, Glycine soja, etc., and has a certain degree of safety for wheat, corn, and rice and can be used as a herbicide in agriculture, especially for soil treatment. The novel-structured compound of the general formula (I) of the present invention has a significantly better weed control effect than the activity of the prior art during soil treatment / pre-emergence.

[0188] In addition, the compound of the general formula (I) of the present invention is also suitable for the desiccation and / or defoliation of plants. Detailed implementation methods

[0189] 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)

[0190] Synthesis examples

[0191] Preparation of Compound 1-1 in Example 1

[0192]

[0193] 1) Preparation of (E)-2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)benzaldehyde oxime

[0194] 6.38 g (0.04 mol) of 2-fluoro-4-chloro-5-methylaniline and 6.72 g (0.08 mol) of sodium bicarbonate were successively added to 50 ml of ethyl acetate, and the temperature was raised to a slightly reflux state. 4.88 g (0.045 mol) of ethyl chloroformate was added dropwise, and the reflux was maintained for 4 hours. The reaction was complete by HPLC. After cooling to room temperature, water was added, and the layers were separated. The organic phase was washed with saturated brine, and the solvent was distilled off under reduced pressure to obtain 9.4 g of an oily substance with a content of 98% (HPLC normalization, the same below).

[0195] The above-mentioned oily substance and 50 ml of acetonitrile were added to a reaction flask containing 50 ml of DMF, 5.66 g (0.041 mol) of potassium carbonate, 7.5 g (0.041 mol) of ethyl 3-amino-4,4,4-trifluorocrotonate, and 0.5 g (1.5 mmol) of tetrabutylammonium bromide. The temperature was raised to reflux. After 4 hours, the reaction ended by HPLC. After cooling to room temperature, 5.66 g (0.041 mol) of potassium carbonate was added, and 8.52 g (0.06 mol) of methyl iodide was added dropwise. Stirring was maintained at room temperature for 4 hours. The reaction was complete by HPLC. The reaction solution was slowly poured into water, stirred for 30 minutes, filtered and dried to obtain 12.8 g of a light yellow solid with a content of 97.8% and a melting point of 117-119 °C.

[0196] 6.9 g (0.02 mol) of the above-mentioned light yellow solid, 7.85 g (0.044 mol) of NBS, 0.35 g (2.13 mmol) of azobisisobutyronitrile, and 50 ml of carbon tetrachloride were successively added to the reaction flask, and the temperature was raised to reflux for reaction. After 2 hours, 1.1 g of NBS was added, and the reaction continued for 2 hours. The reaction was complete by HPLC. The content of the dibromide was 91.8%, and the content of the monobromide was 3.85%. After cooling to room temperature, 50 ml of 1N HCl was added, and the organic phase was separated. The aqueous phase was extracted with 100 ml of dichloromethane to separate the organic phase. The organic phases were combined, the solvent was removed under reduced pressure, and then 50 ml of 88% formic acid was added, and the temperature was raised to reflux and kept warm for 6 hours. The solvent was distilled off under reduced pressure, carefully added to water, and the pH was adjusted to 9 with sodium hydroxide, stirred for 15 minutes, filtered and dried to obtain 6.64 g of a light yellow solid with a content of 94.5% and a melting point of 176-177 °C.

[0197] 6.64 g (0.018 mol) of the above-mentioned light yellow solid was added to 50 ml of ethanol, stirred at room temperature for 10 minutes, and then a mixture of 1.44 g (0.02 mol) of hydroxylamine hydrochloride and 10 ml of water was added dropwise, followed by stirring at room temperature to gradually form a light yellow turbid solution. After the reaction for 1 hour, the HPLC reaction ended, the reaction was stopped, allowed to stand, filtered, washed with 50 mL of water, and dried to obtain 6.49 g of a light yellow solid with a content of 96.1% and a melting point of 182 - 185 °C.

[0198] 2) Preparation of Compound 1-1

[0199] 0.76 g (2 mmol) of (E)-2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)benzaldoxime was dissolved in 20 ml of dichloromethane and 5 ml of N,N-dimethylformamide, and the temperature was raised to 35 °C. At this temperature, 0.28 g (2.1 mmol) of NCS was carefully added, and the reaction was maintained at this temperature for 1 hour. The temperature was lowered to 0 - 5 °C, and a mixture of 0.16 g (2.2 mmol) of 2-methoxypropene, 0.22 g (2.2 mmol) of triethylamine, and 5 ml of dichloromethane was added dropwise. The reaction was maintained at this temperature for 1.5 hours. After the HPLC monitoring showed the reaction was complete, 50 ml of dichloromethane was added, followed by 100 ml of water. The organic phase was separated, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Column chromatography (ethyl acetate:petroleum ether = 1:10) gave 0.26 g of an oily substance. 1 1H-NMR (600 MHz, internal standard TMS, solvent CDCl 3 ) δ (ppm): 7.71 (d, 1H), 7.35 (d, 1H), 6.36 (s, 1H), 3.56 (s, 3H), 3.52 - 3.35 (m, 2H), 3.31 (d, 3H), 1.72 (s, 3H).

[0200] Referring to the synthesis of Compound 1-1 in Example 1, in Step 2, 2-methoxypropene was replaced with 2-ethoxypropene, methyl 2-methoxyacrylate, ethyl 2-methoxyacrylate, and ethyl 2-acetoxyacrylate, respectively, to obtain Compounds 1-2, 1-187, 1-188, and 1-254, respectively.

[0201] The physical properties and NMR data of some compounds are shown in Table 9.

[0202] Table 9

[0203]

[0204] The corresponding aniline can refer to CN105646328 and US5705644 to obtain methyl intermediates VI-2 and VI-3. Then, after further obtaining the corresponding aldehyde according to the synthesis examples and reacting it with a substituted olefin, other compounds described in the general formula I can be obtained.

[0205] Biological activity assay

[0206] Example 2 Indoor herbicidal activity assay

[0207] The herbicidal activity test method of the compounds of the present invention is as follows:

[0208] Quantitative seeds of gramineous weeds (Echinochloa crusgalli, Setaria glauca) and broad-leaved weeds (Zinnia elegans, Abutilon theophrasti) are sown in paper cups with a diameter of 7 cm filled with nutrient soil. After sowing, cover the soil with 1 cm of soil, compact and water, and then cultivate in the greenhouse according to the conventional method. Pre-emergence soil spraying treatment is carried out 24 hours after sowing; post-emergence foliar spraying treatment is carried out when the gramineous weeds grow to the 2-3 leaf stage and the broad-leaved weeds grow to the 2-4 leaf stage. According to the test design dose, carry out spraying treatment on a crawler crop sprayer (designed and produced by Engineer Research Ltd., UK) (spraying pressure 1.95 kg / cm 2 , spray liquid volume 500 L / hm 2 , crawler speed 1.48 km / h). The test is set with 3 replicates. After the test materials are treated, place them in the operation hall. After the liquid medicine dries naturally, place them in the greenhouse and manage them according to the conventional method. Observe and record the reaction of the weeds to the medicament, and regularly visually observe the control effect of the test medicament on the weeds after treatment.

[0209] Control effect grading standard: 0 means ineffective, and 100% means completely killing or severely inhibiting the weeds.

[0210] After the herbicidal activity test, compounds 1-1, 1-2, 1-187, 1-188, 1-254, etc. have a herbicidal activity of more than 80% against Zinnia elegans, Abutilon theophrasti, Setaria viridis and Echinochloa crusgalli at the dose of 600 g a.i. / hm 2 , showing relatively high activity in both pre-emergence and post-emergence treatments. At the same time, further compare the obtained compounds with the prior art, and the data are shown in Table 10 (all mass concentrations are calculated based on the active ingredient).

[0211] Table 10

[0212]

[0213] Example 3 Indoor safety assay

[0214] Quantitative seeds of crops (soybean, cotton, corn, wheat, rice) were sown separately in paper cups with a diameter of 9 cm filled with nutrient soil. After sowing, the soil was covered with a 1-cm layer of soil, compacted, and watered. Then, they were cultivated in a greenhouse according to the conventional method. For gramineous crops, foliar spray treatment was carried out at the 3-leaf stage, and for broad-leaved crops, foliar spray treatment was carried out at the 2-4 leaf stage (1-2 trifoliolate leaves). Pre-emergence soil spray treatment was carried out 24 hours after sowing. According to the test design dose, spray treatment was carried out on a crawler-type crop sprayer (designed and produced by Engineer Research Ltd., UK) (spray pressure 1.95 kg / cm 2 , spray volume 500 L / ha, crawler speed 1.48 km / h). The test was set with 3 replicates. After the test materials were treated, they were placed in the operation hall. After the liquid medicine dried naturally, they were placed in the greenhouse and managed according to the conventional method. The responses of the test crops to the medicaments were observed and recorded, and the safety of the test medicaments to the crops was visually investigated regularly after treatment. Safety grading standard: 0 indicates no damage to the crops, and 100 indicates that the crops are completely killed or severely inhibited.

[0215] Through indoor safety determination, it was found that compounds 1-1, 1-2, 1-187, 1-188, 1-254, etc. had good safety for wheat, corn, and soybean at the pre-emergence doses of 9.4 and 18.75 g a.i. / hm 2 .

Claims

1. An arylisoxazoline compound, as shown in the general formula (I): In the formula: R 1 and R 2 are each independently selected from hydrogen, fluorine, chlorine, and bromine; R 3 selected from hydrogen, methyl; R 4 selected from hydrogen or methyl; R 5 selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl; R 6 selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl; Q is selected from Q1 R 11 Selected from trifluoromethyl; R 12 selected from methyl; X is selected from C or N; R 5 and OR 6 The carbon atoms connected by the "and" or "OR" are asymmetric carbon atoms, and their configurations are R or S; or an agriculturally acceptable salt of the compound shown in formula (I).

2. Use of the compound of general formula (I) according to claim 1 for controlling weeds.

3. A herbicidal composition, characterized in that: using the compound of general formula (I) according to claim 1 as an active ingredient, and the weight percentage of the active ingredient in the composition is 0.1-99%.

4. Use of the herbicidal composition according to claim 3 for controlling weeds.

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