Phenyl isoxazoline ester compound and application thereof

Abstract

The invention belongs to the field of agricultural herbicides, and particularly relates to a phenyl isoxazoline ester compound and application thereof. The phenyl isoxazoline ester compound is shown in a general formula (I), the compound in the general formula (I) has good herbicidal activity, can effectively control weeds such as barnyard grass, green bristlegrass, cyperus difformis, juncellus serotinus, digitaria sanguinalis, hispid arthraxon, piemarker, zinnia elegans, amaranthus retroflexus, portulaca oleracea, xanthium sibiricum, solanum nigrum, cassia occidentalis, capparis spinosa and wild soybean, and a good herbicidal effect can be obtained at a low dosage. The weeding composition has good safety to crops such as corn, wheat and rice, and can be used as a herbicide in agriculture. # imgabs0 #

Description

Technical Field

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

[0002] There are many patent reports on the research of phenylisoxazoline compounds as herbicides. For example, it is disclosed in both CN105753853 and WO2014048827 that phenylisoxazoline compounds have certain herbicidal activities. Although the disclosed compounds in the prior art 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 all have better herbicidal activities. Summary of the Invention

[0003] In order to develop new herbicides to solve the increasingly serious problem of herbicide resistance, the present invention provides a phenylisoxazoline ester compound and its use.

[0004] To achieve the above object, the technical solution adopted by the present invention is as follows:

[0005] A phenylisoxazoline ester compound, as shown in the general formula (I):

[0006]

[0007] In the formula:

[0008] R1 and R2 are each independently selected from hydrogen, halogen or C1-C6 alkyl;

[0009] R3 is selected from hydrogen, cyano or C1-C6 alkyl;

[0010] R4 is selected from hydrogen, cyano, C1-C6 alkyl or CO2R7;

[0011] R5 is selected from hydrogen, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 haloalkyl, CH2SiC[tris(C1-C6 alkyl)], phenyl which is unsubstituted or substituted by 1-4 groups independently selected from the following groups: halogen, CN, NO2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylthio or C1-C6 alkylsulfonyl;

[0012] R6 is selected from C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkyl CO2R7, phenyl, phenyl C1-C6 alkyl which is unsubstituted or substituted by 1-4 groups independently selected from the following groups: halogen, CN, NO2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylthio or C1-C6 alkylsulfonyl;

[0013] R7 is selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkoxycarbonyloxy C2-C4 alkyl, C2-C6 alkenyloxycarbonyloxy C2-C4 alkyl, bis(C1-C6 alkyl)amino C2-C4 alkyl, (C1-C6 alkyl)amino C2-C4 alkyl, phenyl, benzyl, furfurylidene, thiazolylidene, tetrahydrofurfurylidene or pyridylidene which is unsubstituted or substituted by 1-4 groups independently selected from the following groups: halogen, CN, NO2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylthio or C1-C6 alkylsulfonyl;

[0014] Q is selected from any one of Q1-Q17 as follows;

[0015]

[0016] R8 is selected from C1-C6 alkyl or C1-C6 haloalkyl;

[0017] R9 is selected from C1-C6 alkyl, C1-C6 haloalkyl or NH2;

[0018] R 10 is selected from C1-C6 alkyl or C1-C6 haloalkyl;

[0019] R 11 is selected from C1-C6 alkyl or C1-C6 haloalkyl;

[0020] R 12 is selected from C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy;

[0021] R 13 is selected from hydrogen, halogen, CN, NO2 or C1-C6 alkyl;

[0022] R 14Selected from C1-C6 alkyl or C1-C6 haloalkyl;

[0023] R 15 Selected from C1-C6 alkyl, C3-C6 cycloalkyl or C1-C6 haloalkyl;

[0024] R 16 Selected from hydrogen, halogen, cyano, nitro, C1-C6 alkyl or C1-C6 haloalkyl;

[0025] R 17 Selected from hydrogen, halogen, nitro or cyano;

[0026] Or, the optical isomers, agriculturally acceptable salts or derivatives of the compound of formula (I).

[0027] Preferably, in general formula (I)

[0028] R1 and R2 are each independently selected from hydrogen, halogen or C1-C4 alkyl;

[0029] R3 is selected from hydrogen, cyano or C1-C4 alkyl;

[0030] R4 is selected from hydrogen, cyano, C1-C4 alkyl or CO2R7;

[0031] R5 is selected from hydrogen, cyano, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C1-C4 haloalkyl, CH2Si[tris(C1-C6 alkyl)], phenyl which is unsubstituted or substituted by 1-4 groups independently selected from the following: halogen, CN, NO2, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy;

[0032] R6 is selected from C1-C6 alkyl, C1-C6 alkoxy C1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C4 alkyl, C1-C6 alkyl CO2R7, phenyl which is unsubstituted or substituted by 1-4 groups independently selected from the following, phenyl C1-C4 alkyl: halogen, CN, NO2, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy;

[0033] R7 is selected from hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxyC1-C6 alkyl, C1-C6 alkoxycarbonyloxyC2-C4 alkyl, C2-C6 alkenyloxycarbonyloxyC2-C4 alkyl, bis(C1-C6 alkyl)aminoC2-C4 alkyl, (C1-C6 alkyl)aminoC2-C4 alkyl, phenyl, benzyl, furfurylidene or tetrahydrofurfurylidene which is unsubstituted or substituted by 1-4 groups independently selected from the following groups: halogen, CN, NO2, C1-C4 alkyl, C1-C8 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy or C1-C4 alkoxycarbonyl;

[0034] Q is selected from any one of the following Q1-Q17;

[0035] R8 is selected from C1-C4 alkyl or C1-C4 haloalkyl;

[0036] R9 is selected from C1-C4 alkyl, C1-C4 haloalkyl or NH2;

[0037] R 10 is selected from C1-C6 alkyl or C1-C6 haloalkyl;

[0038] R 11 is selected from C1-C4 alkyl or C1-C4 haloalkyl;

[0039] R 12 is selected from C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy;

[0040] R 13 is selected from hydrogen, halogen, CN, NO2 or C1-C4 alkyl;

[0041] R 14 is selected from C1-C4 alkyl or C1-C4 haloalkyl;

[0042] R 15 is selected from C1-C4 alkyl, C3-C6 cycloalkyl or C1-C4 haloalkyl;

[0043] R 16 is selected from hydrogen, halogen, cyano, nitro, C1-C4 alkyl or C1-C4 haloalkyl;

[0044] R 17 is selected from hydrogen, halogen, nitro or cyano;

[0045] or an optically active isomer, an agriculturally usable salt or a derivative of the compound of formula (I).

[0046] More preferably, in the general formula (I)

[0047] R1 and R2 are each independently selected from hydrogen, halogen, methyl, ethyl, propyl or isopropyl;

[0048] R3 is selected from hydrogen, cyano or C1-C4 alkyl;

[0049] R4 is selected from hydrogen, cyano or C1-C4 alkyl;

[0050] R5 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, vinyl, allyl, propargyl, butenyl, butynyl, trifluoromethyl, difluoromethyl, trifluoroethyl, CH2SiC(CH3)3, phenyl which is unsubstituted or substituted with 1-2 groups independently selected from the following groups: fluorine, chlorine, bromine, CN, NO2, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, tert-butoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy or difluoroethoxy;

[0051] R6 is selected from C1-C4 alkyl, C1-C4 alkoxy C1-C3 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C2 alkyl, CH2CO2R7, CH(CH3)CO2R7, C(CH3)2CO2R7, CH(C2H5)CO2R7, CH2CH2CO2R7, phenyl or phenyl C1-C2 alkyl which is unsubstituted or substituted with 1-2 groups independently selected from the following groups: fluorine, chlorine, bromine, CN, NO2, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, tert-butoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy or difluoroethoxy;

[0052] R7 is selected from hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl or C1-C6 alkoxy C1-C6 alkyl;

[0053] Q is selected from any one of Q1-Q17 as follows;

[0054] R8 is selected from C1-C4 alkyl or C1-C4 haloalkyl;

[0055] R9 is selected from C1-C4 alkyl or NH2;

[0056] R 10 is selected from C1-C4 alkyl;

[0057] R 11 is selected from C1-C4 alkyl or C1-C2 haloalkyl;

[0058] R 12Selected from C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy;

[0059] R 13 Selected from hydrogen, halogen or C1-C4 alkyl;

[0060] R 14 Selected from C1-C4 alkyl or C1-C2 haloalkyl;

[0061] R 15 Selected from C1-C4 alkyl, C3-C6 cycloalkyl or C1-C2 haloalkyl;

[0062] R 16 Selected from hydrogen, halogen, cyano, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, trifluoroethyl;

[0063] R 17 Selected from hydrogen, halogen, nitro or cyano;

[0064] Or, the optical isomers, agriculturally-usable salts or derivatives of the compound of formula (I).

[0065] Further preferably, in the general formula (I)

[0066] R1 and R2 are each independently selected from hydrogen, fluorine, chlorine, bromine or methyl;

[0067] R3 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl;

[0068] R4 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl or tert-butyl;

[0069] R5 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, vinyl, allyl, propargyl, butenyl, butynyl, trifluoromethyl, difluoromethyl, trifluoroethyl, CH2SiC(CH3)3, phenyl which is unsubstituted or substituted by 1-2 groups independently selected from the following: fluorine, chlorine, bromine, CN, NO2, methyl, isopropyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy;

[0070] R6 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxyethyl, ethoxyethyl, propoxyethyl, isopropoxyethyl, methoxypropyl, ethoxypropyl, trifluoromethyl, trifluoroethyl, difluoromethyl, difluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethylene, cyclopentylmethylene, cyclohexylmethylene, CH2CO2R7, CH(CH3)CO2R7, C(CH3)2CO2R7, CH(C2H5)CO2R7, CH2CH2CO2R7, phenyl or benzyl which is unsubstituted or substituted by 1-2 groups independently selected from the following groups: fluorine, chlorine, bromine, CN, NO2, methyl, isopropyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy;

[0071] R7 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, trifluoroethyl, difluoromethyl, difluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl, allyl, propargyl, butenyl, butynyl, methoxyethyl, ethoxyethyl, propoxyethyl, isopropoxyethyl, methoxypropyl or ethoxypropyl;

[0072] Q is selected from any one of the following Q1-Q17;

[0073] R8 is selected from methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, trifluoroethyl, difluoromethyl, 1,1-difluoroethyl or 2,2-difluoroethyl;

[0074] R9 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl or NH2;

[0075] R 10 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl;

[0076] R 11 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, difluoromethyl, trifluoroethyl, 1,1-difluoroethyl or 2,2-difluoroethyl;

[0077] 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;

[0078] R 13 is selected from hydrogen, fluorine, chlorine, bromine, methyl or ethyl;

[0079] R 14selected from methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, difluoromethyl, trifluoroethyl, 1,1-difluoroethyl or 2,2-difluoroethyl;

[0080] R 15 selected from methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, cyclopropyl, difluoromethyl, trifluoromethyl, trifluoroethyl, 1,1-difluoroethyl or 2,2-difluoroethyl;

[0081] R 16 selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, trifluoroethyl;

[0082] R 17 selected from hydrogen, fluorine, chlorine, bromine, iodine, nitro or cyano;

[0083] or, an optically active isomer, an agriculturally usable salt or a derivative of the compound of formula (I).

[0084] More preferably, in the general formula (I)

[0085] R1 and R2 are each independently selected from hydrogen, fluorine, chlorine or bromine;

[0086] R3 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl;

[0087] R4 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl or tert-butyl;

[0088] R5 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, vinyl, allyl, propargyl, trifluoromethyl, difluoromethyl, trifluoroethyl, CH2SiC(CH3)3, phenyl or benzyl which is unsubstituted or substituted by 1-2 groups independently selected from the following: fluorine, chlorine or bromine;

[0089] R6 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxyethyl, ethoxyethyl, propoxyethyl, isopropoxyethyl, methoxypropyl, ethoxypropyl, trifluoromethyl, trifluoroethyl, difluoromethyl, difluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethylene, cyclopentylmethylene, cyclohexylmethylene, CH2CO2R7, CH(CH3)CO2R7, C(CH3)2CO2R7, CH(C2H5)CO2R7, CH2CH2CO2R7, phenyl or benzyl which is unsubstituted or substituted by 1-2 groups independently selected from the following: fluorine, chlorine or bromine;

[0090] R7 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, trifluoroethyl, difluoromethyl, difluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl, allyl, propargyl, butenyl, butynyl, methoxyethyl, ethoxyethyl, propoxyethyl, isopropoxyethyl, methoxypropyl or ethoxypropyl;

[0091] Q is selected from the following Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q16 or Q17;

[0092] R8 is selected from methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, trifluoroethyl, difluoromethyl, 1,1-difluoroethyl or 2,2-difluoroethyl;

[0093] R9 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl or NH2;

[0094] R 10 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl;

[0095] R 11 is selected from methyl, ethyl, isopropyl, tert-butyl, difluoromethyl, trifluoroethyl, 1,1-difluoroethyl or 2,2-difluoroethyl;

[0096] R 12 is selected from methyl, trifluoromethyl, difluoromethyl, methoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, trifluoroethoxy or difluoroethoxy;

[0097] R 13 is selected from hydrogen, fluorine, chlorine, bromine or methyl;

[0098] R 14 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl or tert-butyl;

[0099] R 15 is selected from methyl, cyclopropyl or trifluoromethyl;

[0100] R 16 is selected from hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl or trifluoromethyl;

[0101] R 17 is selected from hydrogen, fluorine, chlorine, bromine, nitro or cyano;

[0102] or the optical isomers, agriculturally acceptable salts or derivatives of the compound of formula (I).

[0103] More preferably, in the general formula (I)

[0104] R1 and R2 are each independently selected from hydrogen, fluorine or chlorine;

[0105] R3 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl;

[0106] R4 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl or tert-butyl;

[0107] R5 is selected from hydrogen, methyl, ethyl, trifluoromethyl, vinyl, allyl, propargyl, CH2SiC(CH3)3, phenyl which is unsubstituted or substituted by 1-2 groups independently selected from the following: fluorine, chlorine or bromine;

[0108] R6 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxyethyl, ethoxyethyl, propoxyethyl, isopropoxyethyl, methoxypropyl, ethoxypropyl, trifluoromethyl, trifluoroethyl, difluoromethyl, difluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethylene, cyclopentylmethylene, cyclohexylmethylene, CH2CO2R7, CH(CH3)CO2R7, C(CH3)2CO2R7, CH(C2H5)CO2R7, CH2CH2CO2R7, phenyl or benzyl which is unsubstituted or substituted by 1-2 groups independently selected from the following: fluorine, chlorine or bromine;

[0109] R7 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, trifluoroethyl, difluoromethyl, difluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl, allyl, propargyl, butenyl or butynyl;

[0110] Q is selected from the following Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12 or Q17;

[0111] R8 is selected from trifluoromethyl, trifluoroethyl, difluoromethyl, 1,1-difluoroethyl or 2,2-difluoroethyl;

[0112] R9 is selected from methyl, ethyl, n-propyl, isopropyl or NH2;

[0113] R 10 is selected from methyl, ethyl, n-propyl or isopropyl;

[0114] R 11 is selected from methyl, ethyl, isopropyl, tert-butyl, difluoromethyl, trifluoroethyl, 1,1-difluoroethyl or 2,2-difluoroethyl;

[0115] R 12 is selected from methyl, trifluoromethyl, difluoromethyl, methoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, trifluoroethoxy or difluoroethoxy;

[0116] R 13 is selected from hydrogen, chlorine, bromine or methyl;

[0117] R 14 is selected from methyl, ethyl, n-propyl, isopropyl, isobutyl or tert-butyl;

[0118] R 16 is selected from hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl or trifluoromethyl;

[0119] R 17 is selected from hydrogen, fluorine, chlorine, bromine, nitro or cyano;

[0120] or an optically active isomer, agriculturally acceptable salt or derivative of the compound of formula (I).

[0121] Most preferably, in the general formula (I)

[0122] R1 and R2 are each independently selected from hydrogen, fluorine or chlorine;

[0123] R3 is selected from hydrogen, methyl or ethyl;

[0124] R4 is selected from hydrogen or methyl;

[0125] R5 is selected from hydrogen, methyl, ethyl, trifluoromethyl or vinyl;

[0126] R6 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxyethyl, ethoxyethyl, trifluoromethyl, trifluoroethyl, difluoromethyl, difluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethylene, cyclopentylmethylene, cyclohexylmethylene, CH2CO2R7, CH(CH3)CO2R7, C(CH3)2CO2R7, CH(C2H5)CO2R7, CH2CH2CO2R7, benzyl which is unsubstituted or substituted with 1-2 groups independently selected from the following: fluorine, chlorine or bromine;

[0127] R7 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, allyl or propargyl;

[0128] Q is selected from the following Q1, Q2, Q3, Q4, Q9, Q11, Q12 or Q17;

[0129] R8 is selected from trifluoromethyl, trifluoroethyl, difluoromethyl, 1,1-difluoroethyl or 2,2-difluoroethyl;

[0130] R9 is selected from methyl or NH2;

[0131] R 10 is selected from methyl or ethyl;

[0132] R11 selected from methyl or difluoromethyl;

[0133] R 12 selected from methyl, trifluoromethyl, difluoromethyl, isopropoxy, difluoromethoxy, trifluoroethoxy or difluoroethoxy;

[0134] R 13 selected from chlorine, bromine or methyl;

[0135] R 14 selected from methyl, isopropyl, isobutyl or tert-butyl;

[0136] R 16 selected from trifluoromethyl;

[0137] R 17 selected from hydrogen, fluorine, chlorine or bromine;

[0138] or an optical isomer, agriculturally acceptable salt or derivative of the compound of formula (I).

[0139] Use of a compound of the general formula (I) as defined above for controlling weeds.

[0140] In the definitions of the compounds of general formula (I) given above, the terms used generally have the following definitions:

[0141] Halogen: refers to fluorine, chlorine, bromine or iodine. Alkyl: straight-chain or branched-chain alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl or tert-butyl. Cycloalkyl: substituted or unsubstituted cyclic alkyl, such as cyclopropyl, cyclopentyl or cyclohexyl. Substituents such as methyl, halogen, etc. Haloalkyl: straight-chain or branched-chain alkyl in which the hydrogen atoms on these alkyls 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 bonded to the structure through an oxygen atom. Haloalkoxy: straight-chain or branched-chain alkoxy in which the hydrogen atoms on these alkoxys 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 bonded to the structure through a sulfur atom. Haloalkylthio: straight-chain or branched-chain alkylthio in which the hydrogen atoms on these alkyls 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 is bonded to the structure through a sulfonyl group (-SO2-), such as methylsulfonyl. Haloalkylsulfonyl: straight-chain or branched-chain alkylsulfonyl in which the hydrogen atoms on the alkyl can be partially or completely replaced by halogen atoms. Alkylsulfinyl: straight-chain or branched-chain alkyl is bonded to the structure through a sulfinyl group (-SO-), such as methylsulfinyl. Haloalkylsulfinyl: straight-chain or branched-chain alkylsulfinyl in which the hydrogen atoms on the alkyl can be partially or completely replaced by halogen atoms. Alkoxycarbonyl: alkoxy is bonded to the structure through a carbonyl group, such as CH3OCO- or CH3CH2OCO-. Alkoxyalkyl: alkyl-O-alkyl-, such as CH3OCH2-. Alkylcarbonyloxyalkoxycarbonyl: alkyl-CO-O-alkyl-OCO-, such as CH3COOCH2OCO-, CH3COOCH2CH2OCO- or C2H5COOCH2CH2OCO-, etc. Alkylcarbonyl: alkyl is bonded to the structure through a carbonyl group, such as CH3CO- or CH3CH2CO-, etc. Haloalkylcarbonyl: haloalkyl is bonded to the structure through a carbonyl group, such as CF3CO- or CF2HCO-, etc. Cycloalkylcarbonyl: cycloalkyl is bonded to the structure through a carbonyl group, such as cyclopropanecarbonyl or cyclohexanecarbonyl, etc. Halocycloalkylcarbonyl: halocycloalkyl is bonded to the structure through a carbonyl group, such as 1-chlorocyclopropanecarbonyl, etc. Alkylaminosulfonyl: alkyl-NH-SO2-, such as CH3NHSO2- or C2H5NHSO2-, etc. Dialkylaminosulfonyl: dialkyl-N-SO2-, such as (CH3)2NSO2- or (C2H5)2NSO2-, etc.Alkylaminocarbonyl: alkyl-NH-CO-, such as CH3NHCO- or C2H5NHCO-, etc. Dialkylaminocarbonyl: dialkyl-N-CO-, such as (CH3)2NCO- or (C2H5)2NCO-, etc. Dialkylaminothiocarbonyl: dialkyl-N-CS-, such as (CH3)2NCS- or (C2H5)2NCS-, etc. Alkylthioalkylcarbonyl: alkyl-S-alkyl-CO, such as CH3SCH2CO or CH3SCH2CH2CO, 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. SO2NH(C1-C4 alkyl): -SO2NHCH3 or -SO2NHC2H5, etc. SO2N(C1-C2 alkyl)(C1-C4 alkyl):.

[0142] -SO2N(CH3)2 or -SO2N(CH3)[CH(CH3)2], etc.

[0143] Some compounds of the present invention can be illustrated by the specific compounds listed in Tables 1-54, but the present invention is not limited to these compounds.

[0144] Table 1: In general formula I, Q = Q1, R3 = H, R4 = H, R8 = CF3, R9 = CH3, and the specific values of R1, R2, R5, and R6 are shown in the following table. The corresponding compound numbers are 1-1 to 1-232.

[0145]

[0146] Table 1

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154] Table 2: In general formula I, Q = Q1, R3 = H, R4 = H, R8 = CH3CF2, R9 = CH3, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 2-1 to 2-232 correspond to 1-1 to 1-232 in Table 1.

[0155] Table 3: In general formula I, Q = Q1, R3 = H, R4 = H, R8 = CH3CF2, R9 = NH2, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 3-1 to 3-232 correspond to 1-1 to 1-232 in Table 1.

[0156] Table 4: In general formula I, Q = Q1, R3 = H, R4 = H, R8 = CF3, R9 = NH2, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 4-1 to 4-232 correspond to 1-1 to 1-232 in Table 1.

[0157] Table 5: In general formula I, Q = Q2, R3 = H, R4 = H, R9 = CH3, R 10 = CH3, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 5-1 to 5-232 correspond to 1-1 to 1-232 in Table 1.

[0158] Table 6: In general formula I, Q = Q3, R3 = H, R4 = H, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 6-1 to 6-232 correspond to 1-1 to 1-232 in Table 1.

[0159] Table 7: In general formula I, Q = Q4, R3 = H, R4 = H, R 11 = CH3, R 12 = OCHF2, R 13 = Cl, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 7-1 to 7-232 correspond to 1-1 to 1-232 in Table 1.

[0160] Table 8: In general formula I, Q = Q4, R3 = H, R4 = H, R 11 = CH3, R 12 = OCHF2, R 13 = Br, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 8-1 to 8-232 correspond to 1-1 to 1-232 in Table 1.

[0161] Table 9: In general formula I, Q = Q4, R3 = H, R4 = H, R 11 = CH3, R 12 = CF3, R 13 = Cl, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 9-1 to 9-232 correspond to 1-1 to 1-232 in Table 1.

[0162] Table 10: In general formula I, Q = Q4, R3 = H, R4 = H, R 11 = CH3, R 12 = CF3, R 13= Br, R1, R2, R5, and R6 are specifically shown in Table 1, and Compounds 10-1 to 10-232 correspond to 1-1 to 1-232 in Table 1.

[0163] Table 11: In General Formula I, Q = Q5, R3 = H, R4 = H, R 11 = CHF2, R 12 = CH3, R1, R2, R5, and R6 are specifically shown in Table 1, and Compounds 11-1 to 11-232 correspond to 1-1 to 1-232 in Table 1.

[0164] Table 12: In General Formula I, Q = Q6, R3 = H, R4 = H, R 13 = Br, R1, R2, R5, and R6 are specifically shown in Table 1, and Compounds 2-1 to 2-232 correspond to 12-1 to 12-232 in Table 1.

[0165] Table 13: In General Formula I, Q = Q7, R3 = H, R4 = H, R 13 = Cl, R1, R2, R5, and R6 are specifically shown in Table 1, and Compounds 2-1 to 2-232 correspond to 13-1 to 13-232 in Table 1.

[0166] Table 14: In General Formula I, Q = Q8, R3 = H, R4 = H, R 12 = CF3, R 13 = Br, R1, R2, R5, and R6 are specifically shown in Table 1, and Compounds 14-1 to 14-232 correspond to 1-1 to 1-232 in Table 1.

[0167] Table 15: In General Formula I, Q = Q8, R3 = H, R4 = H, R 12 = CF3, R 13 = CH3, R1, R2, R5, and R6 are specifically shown in Table 1, and Compounds 15-1 to 15-232 correspond to 1-1 to 1-232 in Table 1.

[0168] Table 16: In General Formula I, Q = Q9, R3 = H, R4 = H, R 14 = C(CH3)3, R1, R2, R5, and R6 are specifically shown in Table 1, and Compounds 16-1 to 16-232 correspond to 1-1 to 1-232 in Table 1.

[0169] Table 17: In General Formula I, Q = Q10, R3 = H, R4 = H, R1, R2, R5, and R6 are specifically shown in Table 1, and Compounds 17-1 to 17-232 correspond to 1-1 to 1-232 in Table 1.

[0170] Table 18: In General Formula I, Q = Q11, R3 = H, R4 = H, R1, R2, R5, and R6 are specifically shown in Table 1, and Compounds 18-1 to 18-232 correspond to 1-1 to 1-232 in Table 1.

[0171] Table 19: In General Formula I, Q = Q12, R3 = H, R4 = H, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 19-1 to 19-232 correspond to 1-1 to 1-232 in Table 1.

[0172] Table 20: In General Formula I, Q = Q13, R3 = H, R4 = H, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 20-1 to 20-232 correspond to 1-1 to 1-232 in Table 1.

[0173] Table 21: In General Formula I, Q = Q14, R3 = H, R4 = H, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 21-1 to 21-232 correspond to 1-1 to 1-232 in Table 1.

[0174] Table 22: In General Formula I, Q = Q15, R3 = H, R4 = H, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 22-1 to 22-232 correspond to 1-1 to 1-232 in Table 1.

[0175] Table 23: In General Formula I, Q = Q16, R3 = H, R4 = H, R 15 = CH3, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 23-1 to 23-232 correspond to 1-1 to 1-232 in Table 1.

[0176] Table 24: In General Formula I, Q = Q16, R3 = H, R4 = H, R 15 = CF3, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 24-1 to 24-232 correspond to 1-1 to 1-232 in Table 1.

[0177] Table 25: In General Formula I, Q = Q16, R3 = H, R4 = H, R 15 = cyclopropyl, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 25-1 to 25-232 correspond to 1-1 to 1-232 in Table 1.

[0178] Table 26: In General Formula I, General Formula I is the S-isomer, Q = Q1, R3 = H, R4 = H, R8 = CF3, R9 = CH3, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 26-1 to 26-232 correspond to 1-1 to 1-232 in Table 1.

[0179] Table 27: In General Formula I, General Formula I is the S-isomer, Q = Q1, R3 = H, R4 = H, R8 = CH3CF2, R9 = CH3, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 27-1 to 27-232 correspond to 1-1 to 1-232 in Table 1.

[0180] Table 28: In General Formula I, General Formula I is the S-isomer, Q = Q1, R3 = H, R4 = H, R8 = CH3CF2, R9 = NH2, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 28-1 to 28-232 correspond to 1-1 to 1-232 in Table 1.

[0181] Table 29: In General Formula I, General Formula I is the S-isomer, Q = Q1, R3 = H, R4 = H, R8 = CF3, R9 = NH2, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 29-1 to 29-232 correspond to 1-1 to 1-232 in Table 1.

[0182] Table 30: In General Formula I, General Formula I is the S-isomer, Q = Q2, R3 = H, R4 = H, R9 = CH3, R 10 = CH3, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 30-1 to 30-232 correspond to 1-1 to 1-232 in Table 1.

[0183] Table 31: In General Formula I, General Formula I is the S-isomer, Q = Q3, R3 = H, R4 = H, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 31-1 to 31-232 correspond to 1-1 to 1-232 in Table 1.

[0184] Table 32: In General Formula I, General Formula I is the S-isomer, Q = Q4, R3 = H, R4 = H, R 11 = CH3, R 12 = OCHF2, R 13 = Cl, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 32-1 to 32-232 correspond to 1-1 to 1-232 in Table 1.

[0185] Table 33: In General Formula I, General Formula I is the S-isomer, Q = Q4, R3 = H, R4 = H, R 11 = CH3, R 12 = OCHF2, R 13 = Br, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 33-1 to 33-232 correspond to 1-1 to 1-232 in Table 1.

[0186] Table 34: In General Formula I, General Formula I is the S-isomer, Q = Q4, R3 = H, R4 = H, R 11 = CH3, R 12 = CF3, R 13 = Cl, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 34-1 to 34-232 correspond to 1-1 to 1-232 in Table 1.

[0187] Table 35: In General Formula I, General Formula I is the S isomer, Q = Q4, R3 = H, R4 = H, R 11 = CH3, R 12 = CF3, R 13 = Br, R1, R2, R5, R6 are specifically shown in Table 1, and Compounds 35-1 to 35-232 correspond to 1-1 to 1-232 in Table 1.

[0188] Table 36: In General Formula I, General Formula I is the S isomer Q = Q5, R3 = H, R4 = H, R 11 = CHF2, R 12 = CH3, R1, R2, R5, R6 are specifically shown in Table 1, and Compounds 36-1 to 36-232 correspond to 1-1 to 1-232 in Table 1.

[0189] Table 37: In General Formula I, General Formula I is the S isomer Q = Q6, R3 = H, R4 = H, R 13 = Br, R1, R2, R5, R6 are specifically shown in Table 1, and Compounds 37-1 to 37-232 correspond to 1-1 to 1-232 in Table 1.

[0190] Table 38: In General Formula I, General Formula I is the S isomer Q = Q7, R3 = H, R4 = H, R 13 = Cl, R1, R2, R5, R6 are specifically shown in Table 1, and Compounds 38-1 to 38-232 correspond to 1-1 to 1-232 in Table 1.

[0191] Table 39: In General Formula I, General Formula I is the S isomer Q = Q8, R3 = H, R4 = H, R 12 = CF3, R 13 = Br, R1, R2, R5, R6 are specifically shown in Table 1, and Compounds 39-1 to 39-232 correspond to 1-1 to 1-232 in Table 1.

[0192] Table 40: In General Formula I, General Formula I is the S isomer Q = Q8, R3 = H, R4 = H, R 12 = CF3, R 13 = CH3, R1, R2, R5, R6 are specifically shown in Table 1, and Compounds 40-1 to 40-232 correspond to 1-1 to 1-232 in Table 1.

[0193] Table 41: In General Formula I, General Formula I is the S isomer Q = Q9, R3 = H, R4 = H, R 14 = C(CH3)3, R1, R2, R5, R6 are specifically shown in Table 1, and Compounds 41-1 to 41-232 correspond to 1-1 to 1-232 in Table 1.

[0194] Table 42: In general formula I, general formula I is the S-isomer, Q = Q10, R3 = H, R4 = H, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 42-1 to 42-232 correspond to 1-1 to 1-232 in Table 1.

[0195] Table 43: In general formula I, general formula I is the S-isomer, Q = Q11, R3 = H, R4 = H, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 43-1 to 43-232 correspond to 1-1 to 1-232 in Table 1.

[0196] Table 44: In general formula I, general formula I is the S-isomer, Q = Q12, R3 = H, R4 = H, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 44-1 to 44-232 correspond to 1-1 to 1-232 in Table 1.

[0197] Table 45: In general formula I, general formula I is the S-isomer, Q = Q13, R3 = H, R4 = H, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 45-1 to 45-232 correspond to 1-1 to 1-232 in Table 1.

[0198] Table 46: In general formula I, general formula I is the S-isomer, Q = Q14, R3 = H, R4 = H, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 46-1 to 46-232 correspond to 1-1 to 1-232 in Table 1.

[0199] Table 47: In general formula I, general formula I is the S-isomer, Q = Q15, R3 = H, R4 = H, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 47-1 to 47-232 correspond to 1-1 to 1-232 in Table 1.

[0200] Table 48: In general formula I, general formula I is the S-isomer, Q = Q16, R3 = H, R4 = H, R 15 = CH3, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 48-1 to 48-232 correspond to 1-1 to 1-232 in Table 1.

[0201] Table 49: In general formula I, general formula I is the S-isomer, Q = Q16, R3 = H, R4 = H, R 15 = CF3, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 49-1 to 49-232 correspond to 1-1 to 1-232 in Table 1.

[0202] Table 50: In general formula I, general formula I is the S-isomer, Q = Q16, R3 = H, R4 = H, R 15 = cyclopropyl, and the specific values of R1, R2, R5, and R6 are shown in Table 1. Compounds 50-1 to 50-232 correspond to 1-1 to 1-232 in Table 1.

[0203] Table 51: In general formula I, Q = Q17, R3 = H, R4 = H, R 16 = CF3, R 17 = Cl, R1, R2, R5, R6 are specifically shown in Table 1, and compounds 51-1 to 51-232 correspond to 1-1 to 1-232 in Table 1.

[0204] Table 52: In general formula I, Q = Q17, R3 = H, R4 = H, R 16 = CF3, R 17 = H, R1, R2, R5, R6 are specifically shown in Table 1, and compounds 52-1 to 52-232 correspond to 1-1 to 1-232 in Table 1.

[0205] Table 53: In general formula I, the general formula I is the S-isomer, Q = Q17, R3 = H, R4 = H, R 16 = CF3, R 17 = Cl, R1, R2, R5, R6 are specifically shown in Table 1, and compounds 53-1 to 53-232 correspond to 1-1 to 1-232 in Table 1.

[0206] Table 54: In general formula I, the general formula I is the S-isomer, Q = Q17, R3 = H, R4 = H, R 16 = CF3, R 17 = H, R1, R2, R5, R6 are specifically shown in Table 1, and compounds 54-1 to 54-232 correspond to 1-1 to 1-232 in Table 1.

[0207] The general formula compound I can be obtained by reacting the general formula II compound with the general formula III mercapto compound. Generally, it can be obtained by reacting II after acyl halide formation with III under alkaline conditions in a suitable solvent, or it can be obtained by reacting in a suitable solvent by adding the corresponding condensing agent.

[0208]

[0209] The acyl halide reagent described above can be selected from thionyl chloride, oxalyl chloride, phosgene, etc.

[0210] The base described above is selected from triethylamine, DMAP, diisopropylethylamine, DBU, N-methylmorpholine, sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, sodium hydroxide, potassium hydroxide, or lithium hydroxide, etc.

[0211] The condensing agent described above can be selected from CDI, DCC, DIC, EDC, EDCl, HBTU, TBTU, HATU, HOAt, BOP, PyBOP, PyBrOP, T3P, or CMPI, etc.

[0212] Suitable solvents may be selected from organic solvents such as acetonitrile, tetrahydrofuran, dioxane, dichloromethane, 1,2 - dichloroethane, chloroform, toluene or DMF, etc.

[0213] The reaction temperature can be from - 10°C to 100°C, usually 20 - 80°C. The reaction time is from 10 minutes to 20 hours, usually 30 minutes - 8 hours.

[0214] The general formula compound II can be obtained by alkaline hydrolysis or acidic hydrolysis of the general formula IV compound, etc.

[0215]

[0216] The said alkaline hydrolysis is that IV reacts in an alcohol solvent or an ether solvent in the presence of sodium hydroxide, potassium hydroxide or lithium hydroxide at - 10°C to 100°C for 10 minutes to 20 hours to obtain the general formula II compound. The said alcohol solvents are methanol, ethanol, isopropanol or tert - butanol, etc.; the said ether solvents are tetrahydrofuran, diethyl ether or dioxane, etc.

[0217] The said acidic hydrolysis is that IV reacts in acetic acid with an appropriate proportion of hydrochloric acid or concentrated sulfuric acid at 40°C to 120°C to obtain the general formula II compound. The appropriate proportion of the said acetic acid to concentrated sulfuric acid or concentrated hydrochloric acid is selected from 1:1 - 10:1.

[0218] Compound IV can be synthesized by referring to the literature such as CN105777733, CN112745269, CN105753853, CN111961041, CN114644622, etc. When IV is an optical isomer, it can be synthesized by referring to CN112679488.

[0219] In general formula IV, Y is selected from methyl, ethyl, n - propyl, isopropyl or tert - butyl.

[0220] Unless otherwise specified, the definitions of each group in the reaction formula are the same as above.

[0221] The compounds of the present invention can effectively control weeds such as barnyard grass, green foxtail, monochoria vaginalis, juncellus 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. It has certain safety for wheat, corn and rice and can be used as a herbicide in agriculture. Therefore, the present invention also includes the use of the general formula (I) compound for controlling weeds.

[0222] In addition, the general formula (I) compound of the present invention is also suitable for the drying and / or defoliation of plants. Detailed implementation mode

[0223] 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)

[0224] Synthesis Example

[0225] Preparation of Compound 1-2 in Example 1

[0226] 3-(2-Chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid (prepared with reference to CN105753853) (0.45 g, 0.001 mol) was added to a reaction flask containing 20 ml of dichloromethane. Under stirring at room temperature, ethanethiol (0.074 g, 0.0012 mol), DMAP (0.03 g, 0.0002 mol), and EDCI (0.38 g, 0.002 mol) were successively added. The reaction mixture was stirred overnight at room temperature, 100 ml of water and 50 ml of dichloromethane were added, and the mixture was extracted and separated into layers. The organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was removed. Column chromatography (ethyl acetate:petroleum ether = 1:5) gave 0.39 g of an oily compound. 1 H NMR(600MHz,Chloroform-d)δ7.67(d,J=7.6Hz,1H),7.33(d,J=8.9Hz,1H),6.35(s,1H),3.85(dd,J=24.4,17.6Hz,1H),3.55(s,3H),3.42(dd,J=21.7,17.7Hz,1H),2.90-2.79(m,2H),1.70(s,3H),1.24(t,3H).HRMS[M+H] + =494.05562;[M+Na] + =516.03733。

[0227] Preparation of Compound 1-3 in Example 2

[0228] With reference to the synthesis of Compound 1-2 in Example 1, ethanethiol was replaced with n-propanethiol. 1 H NMR(600MHz,Chloroform-d)δ7.69(d,J=7.7Hz,1H),7.35(d,J=9.0Hz,1H),6.36(d,J=1.4Hz,1H),3.87(dd,J=25.2,17.6Hz,1H),3.56(s,3H),3.51-3.31(m,1H),1.70(s,3H),1.36-1.25(m,4H),0.93-0.80(m,3H).HRMS[M+H] += 508.07126

[0229] Preparation of Compounds 1-5 in Example 3

[0230] Refer to the synthesis of Compound 1-2 in Example 1 and replace ethanethiol with isopropyl mercaptan. 1 H NMR(600MHz,Chloroform-d)δ7.67(dd,J = 7.7,2.0Hz,1H),7.33(d,J = 9.0Hz,1H),6.35(s,1H),3.85(dd,J = 25.2,17.6Hz,1H),3.56 - 3.53(m,3H),3.42(dd,J = 22.7,17.6Hz,1H),2.88 - 2.75(m,2H),1.69(d,J = 1.7Hz,3H),1.59(pd,J = 7.3,2.5Hz,2H),1.54(s,4H),1.41(s,1H),1.24(s,1H),0.97(td,J = 7.4,2.5Hz,3H). HRMS[M+H] + = 508.07114

[0231] Preparation of Compounds 1-12 in Example 4

[0232] Refer to the synthesis of Compound 1-2 in Example 1 and replace ethanethiol with methyl thioglycolate. HRMS[M+H] + = 538.04962

[0233] Preparation of Compounds 1-229 in Example 5

[0234] Refer to the synthesis of Compound 1-2 in Example 1 and replace ethanethiol with trifluoroethanethiol. 1 H NMR(600MHz,DMSO-d6)δ7.87 - 7.80(m,2H),6.56(d,J = 2.0Hz,1H),3.86(d,J = 1.0Hz,1H),3.84(s,1H),3.81(d,J = 10.5Hz,1H),3.79 - 3.71(m,1H),3.67(dd,J = 17.9,7.3Hz,1H),3.28(s,3H),1.63(s,3H). HRMS[M+H] + = 548.02704

[0235] Preparation of Compound 5-2 in Example 6

[0236] Referring to the synthesis of Compound 1-2 in Example 1, replace 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid with 3-(2-chloro-5-(3,5-dimethyl-2,6-dioxo-4-thio-1,3,5-triazin-1-yl)-4-fluorophenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid (the preparation refers to CN111961041). 1 H NMR(600MHz,DMSO-d6)δ7.74(d,J=7.6Hz,1H),7.36(d,J=9.0Hz,1H),3.87(d,J=17.6Hz,1H),3.77(s,6H),3.43(d,J=17.6Hz,1H),2.86(dd,J=9.5,7.5Hz,2H),1.71(s,3H),1.26(td,J=7.4,1.0Hz,3H).HRMS[M+H] + =473.05098

[0237] Preparation of Compound 5-3 in Example 7

[0238] Referring to the synthesis of Compound 1-2 in Example 1, replace 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid with 3-(2-chloro-5-(3,5-dimethyl-2,6-dioxo-4-thio-1,3,5-triazin-1-yl)-4-fluorophenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid (the preparation refers to CN111961041), and replace ethanethiol with n-propanethiol. 1 H NMR(600MHz,DMSO-d6)δ7.71(d,1H),7.34(d,1H),3.84(d,1H),3.76(s,6H),3.42(d,1H),2.77-2.87(m,2H),1.69(s,3H),1.57-1.63(m,2H),0.97(t,3H).HRMS[M+H] + =487.06684

[0239] Preparation of Compound 5-5 in Example 8

[0240] Referring to the synthesis of Compound 1-2 in Example 1, replace 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-pyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid with 3-(2-chloro-5-(3,5-dimethyl-2,6-dioxo-4-thio-1,3,5-triazin-1-yl)-4-fluorophenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid (preparation reference: CN111961041), and replace ethanethiol with isopropyl mercaptan. 1 H NMR(600MHz,DMSO-d6)δ7.72(d,1H),7.34(d,1H),3.86(d,1H),3.75(s,6H),3.55(m,1H),3.39(d,1H),1.68(s,3H),1.30(dd,6H). HRMS[M+H] + =487.06681

[0241] The present invention also synthesized the following compounds (Table 55) by referring to the method in the above examples:

[0242] Table 55

[0243]

[0244] Biological activity assay

[0245] Indoor herbicidal activity assay of Example 9

[0246] The herbicidal activity test method of the compounds of the present invention is as follows:

[0247] Quantitative seeds of gramineous weeds (Echinochloa crusgalli, Setaria glauca), broad-leaved weeds (Zinnia elegans, Abutilon theophrasti) or sedges are sown in paper cups with a diameter of 7 cm filled with nutrient soil. After sowing, cover the soil with 1 cm, compact and water, and then cultivate in the greenhouse according to the conventional method. When the gramineous weeds grow to the 2-3 leaf stage and the broad-leaved weeds grow to the 2-4 leaf stage, spray the stems and leaves; the pre-emergence soil spray treatment is carried out 24 hours after sowing. According to the test design dose, carry out spray treatment on a crawler crop sprayer (designed and produced by Engineer Research Ltd., UK) (spray 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 in the shade, 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.

[0248] Weed control effect classification standard: 0 means ineffective, and 100% means completely killing or severely inhibiting weeds.

[0249] After herbicidal activity tests, compounds 1-2, 1-3, 1-5, 1-12, 1-229, 2-2, 2-3, 2-5, 5-2, 5-3, 5-5, 26-2, 26-3, 26-5, etc. at a dose of 7.5 g a.i. / hm 2 in post-emergence treatment showed over 95% activity against Zinnia elegans and Abutilon theophrasti, demonstrating relatively high activity.

[0250] The further test results of compound 1-2 are shown in Table 56.

[0251] Table 56 Herbicidal activity results of some compounds

[0252]

[0253] The further activity test results of compound 1-2 and other compounds are shown in Table 57.

[0254] Table 57 Herbicidal activity results of some compounds

[0255]

[0256]

Claims

1. A phenylisoxazoline ester compound, characterized in that: The compound is shown by the general formula (I): Wherein: R1 and R2 are each independently selected from hydrogen, halogen or C1-C6 alkyl; R3 is selected from hydrogen, cyano or C1-C6 alkyl; R4 is selected from hydrogen, cyano, C1-C6 alkyl or CO2R7; R5 is selected from hydrogen, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 haloalkyl, CH2SiC[tri(C1-C6 alkyl)], phenyl which is unsubstituted or substituted by 1-4 groups independently selected from the following groups: halogen, CN, NO2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylthio or C1-C6 alkylsulfonyl; R6 is selected from C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkyl CO2R7, phenyl which is unsubstituted or substituted by 1-4 groups independently selected from the following groups: halogen, CN, NO2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylthio or C1-C6 alkylsulfonyl, phenyl C1-C6 alkyl; R7 is selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkoxycarbonyloxy C2-C4 alkyl, C2-C6 alkenyloxycarbonyloxy C2-C4 alkyl, di(C1-C6 alkyl)amino C2-C4 alkyl, (C1-C6 alkyl)amino C2-C4 alkyl, phenyl, benzyl, furanmethylene, thiazolylmethylene, tetrahydrofuranmethylene or pyridylmethylene which is unsubstituted or substituted by 1-4 groups independently selected from the following groups: halogen, CN, NO2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylthio or C1-C6 alkylsulfonyl; Q is selected from any one of Q1-Q17 as follows; R8 is selected from C1-C6 alkyl or C1-C6 haloalkyl; R9 is selected from C1-C6 alkyl, C1-C6 haloalkyl or NH2; R 10 selected from C1-C6 alkyl or C1-C6 haloalkyl; R 11 selected from C1-C6 alkyl or C1-C6 haloalkyl; R 12 selected from C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy; R 13 selected from hydrogen, halogen, CN, NO2 or C1-C6 alkyl; R 14 selected from C1-C6 alkyl or C1-C6 haloalkyl; R 15 selected from C1-C6 alkyl, C3-C6 cycloalkyl or C1-C6 haloalkyl; R 16 selected from hydrogen, halogen, cyano, nitro, C1-C6 alkyl or C1-C6 haloalkyl; R 17 selected from hydrogen, halogen, nitro or cyano; Or, the optical isomers, agriculturally acceptable salts or derivatives of the compound of formula (I).

2. The compound according to claim 1, wherein: In the general formula (I) R1 and R2 are each independently selected from hydrogen, halogen or C1-C4 alkyl; R3 is selected from hydrogen, cyano or C1-C4 alkyl; R4 is selected from hydrogen, cyano, C1-C4 alkyl or CO2R7; R5 is selected from hydrogen, cyano, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C1-C4 haloalkyl, CH2Si[tris(C1-C6 alkyl)], phenyl which is unsubstituted or substituted by 1-4 groups independently selected from the following: halogen, CN, NO2, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy; R6 is selected from C1-C6 alkyl, C1-C6 alkoxyC1-C4 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C4 alkyl, C1-C6 alkylCO2R7, phenyl which is unsubstituted or substituted by 1-4 groups independently selected from the following, phenylC1-C4 alkyl: halogen, CN, NO2, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy; R7 is selected from hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxyC1-C6 alkyl, C1-C6 alkoxycarbonyloxyC2-C4 alkyl, C2-C6 alkenylcarbonyloxyC2-C4 alkyl, di(C1-C6 alkyl)aminoC2-C4 alkyl, (C1-C6 alkyl)aminoC2-C4 alkyl, phenyl, benzyl, furfurylidene or tetrahydrofurfurylidene which is unsubstituted or substituted by 1-4 groups independently selected from the following, the following groups being: halogen, CN, NO2, C1-C4 alkyl, C1-C8 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy or C1-C4 alkoxycarbonyl; Q is selected from any one of the following Q1-Q17; R8 is selected from C1-C4 alkyl or C1-C4 haloalkyl; R9 is selected from C1-C4 alkyl, C1-C4 haloalkyl or NH2; R 10 selected from C1-C6 alkyl or C1-C6 haloalkyl; R 11 selected from C1-C4 alkyl or C1-C4 haloalkyl; R 12 selected from C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy; R 13 selected from hydrogen, halogen, CN, NO2 or C1-C4 alkyl; R 14 selected from C1-C4 alkyl or C1-C4 haloalkyl; R 15 selected from C1-C4 alkyl, C3-C6 cycloalkyl or C1-C4 haloalkyl; R 16 selected from hydrogen, halogen, cyano, nitro, C1-C4 alkyl or C1-C4 haloalkyl; R 17 selected from hydrogen, halogen, nitro or cyano; or an optically active isomer, agriculturally acceptable salt or derivative of the compound of formula (I).

3. The compound according to claim 2, wherein: In general formula (I) R1 and R2 are each independently selected from hydrogen, halogen, methyl, ethyl, propyl or isopropyl; R3 is selected from hydrogen, cyano or C1-C4 alkyl; R4 is selected from hydrogen, cyano or C1-C4 alkyl; R5 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, vinyl, allyl, propargyl, butenyl, butynyl, trifluoromethyl, difluoromethyl, trifluoroethyl, CH2SiC(CH3)3, phenyl which is unsubstituted or substituted by 1-2 groups independently selected from the following, the following groups being: fluorine, chlorine, bromine, CN, NO2, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, tert-butoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy or difluoroethoxy; R6 is selected from C1-C4 alkyl, C1-C4 alkoxy C1-C3 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C2 alkyl, CH2CO2R7, CH(CH3)CO2R7, C(CH3)2CO2R7, CH(C2H5)CO2R7, CH2CH2CO2R7, phenyl or phenyl C1-C2 alkyl which is unsubstituted or substituted by 1-2 groups independently selected from the following groups: fluorine, chlorine, bromine, CN, NO2, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, tert-butoxy, difluoromethoxy, trifluoromethoxy, trifluoroethoxy or difluoroethoxy; R7 is selected from hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl or C1-C6 alkoxy C1-C6 alkyl; Q is selected from any one of Q1-Q17 as follows; R8 is selected from C1-C4 alkyl or C1-C4 haloalkyl; R9 is selected from C1-C4 alkyl or NH2; R 10 selected from C1-C4 alkyl; R 11 selected from C1-C4 alkyl or C1-C2 haloalkyl; R 12 selected from C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy; R 13 selected from hydrogen, halogen or C1-C4 alkyl; R 14 selected from C1-C4 alkyl or C1-C2 haloalkyl; R 15 selected from C1-C4 alkyl, C3-C6 cycloalkyl or C1-C2 haloalkyl; R 16 selected from hydrogen, halogen, cyano, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, trifluoroethyl; R 17 selected from hydrogen, a halogen, a nitro group or a cyano group; or an optically active isomer, an agriculturally usable salt or a derivative of the compound of formula (I).

4. The compound according to claim 3, characterized in that: In general formula (I) R1 and R2 are each independently selected from hydrogen, fluorine, chlorine, bromine or methyl; R3 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl; R4 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl or tert-butyl; R5 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, vinyl, allyl, propargyl, butenyl, butynyl, trifluoromethyl, difluoromethyl, trifluoroethyl, CH2SiC(CH3)3, phenyl which is unsubstituted or substituted by 1-2 groups independently selected from the following groups: fluorine, chlorine, bromine, CN, NO2, methyl, isopropyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy; R6 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxyethyl, ethoxyethyl, propoxyethyl, isopropoxyethyl, methoxypropyl, ethoxypropyl, trifluoromethyl, trifluoroethyl, difluoromethyl, difluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethylene, cyclopentylmethylene, cyclohexylmethylene, CH2CO2R7, CH(CH3)CO2R7, C(CH3)2CO2R7, CH(C2H5)CO2R7, CH2CH2CO2R7, phenyl, benzyl which is unsubstituted or substituted by 1-2 groups independently selected from the following groups: fluorine, chlorine, bromine, CN, NO2, methyl, isopropyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy; R7 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, trifluoroethyl, difluoromethyl, difluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl, allyl, propargyl, butenyl, butynyl, methoxyethyl, ethoxyethyl, propoxyethyl, isopropoxyethyl, methoxypropyl or ethoxypropyl; Q is selected from any one of the following Q1 - Q17; R8 is selected from methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, trifluoroethyl, difluoromethyl, 1,1-difluoroethyl or 2,2-difluoroethyl; R9 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl or NH2; R 10 selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl; R 11 selected from methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, difluoromethyl, trifluoroethyl, 1,1-difluoroethyl or 2,2-difluoroethyl; R 12 selected from methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, isopropoxy, tert-butoxy, trifluoromethoxy, difluoromethoxy, trifluoroethoxy or difluoroethoxy; R 13 selected from hydrogen, fluorine, chlorine, bromine, methyl or ethyl; R 14 selected from methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, difluoromethyl, trifluoroethyl, 1,1-difluoroethyl or 2,2-difluoroethyl; R 15 selected from methyl, ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, cyclopropyl, difluoromethyl, trifluoromethyl, trifluoroethyl, 1,1-difluoroethyl or 2,2-difluoroethyl; R 16 selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, trifluoroethyl; R 17 selected from hydrogen, fluorine, chlorine, bromine, iodine, nitro or cyano; or, the optical isomers, agriculturally acceptable salts or derivatives of the compound of formula (I).

5. The compound according to claim 4, characterized in that: In general formula (I) R1 and R2 are each independently selected from hydrogen, fluorine, chlorine or bromine; R3 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl; R4 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl or tert-butyl; R5 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, vinyl, allyl, propargyl, trifluoromethyl, difluoromethyl, trifluoroethyl, CH2SiC(CH3)3, phenyl which is unsubstituted or substituted by 1 - 2 groups independently selected from the following: fluorine, chlorine or bromine; R6 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxyethyl, ethoxyethyl, propoxyethyl, isopropoxyethyl, methoxypropyl, ethoxypropyl, trifluoromethyl, trifluoroethyl, difluoromethyl, difluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethylene, cyclopentylmethylene, cyclohexylmethylene, CH2CO2R7, CH(CH3)CO2R7, C(CH3)2CO2R7, CH(C2H5)CO2R7, CH2CH2CO2R7, phenyl or benzyl which is unsubstituted or substituted by 1 - 2 groups independently selected from the following: fluorine, chlorine or bromine; R7 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, trifluoroethyl, difluoromethyl, difluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl, allyl, propargyl, butenyl, butynyl, methoxyethyl, ethoxyethyl, propoxyethyl, isopropoxyethyl, methoxypropyl or ethoxypropyl; Q is selected from the following Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12, Q16 or Q17; R8 is selected from methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, trifluoroethyl, difluoromethyl, 1,1-difluoroethyl or 2,2-difluoroethyl; R9 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl or NH2; R 10 selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl; R 11 selected from methyl, ethyl, isopropyl, tert-butyl, difluoromethyl, trifluoroethyl, 1,1-difluoroethyl or 2,2-difluoroethyl; R 12 selected from methyl, trifluoromethyl, difluoromethyl, methoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, trifluoroethoxy or difluoroethoxy; R 13 selected from hydrogen, fluorine, chlorine, bromine or methyl; R 14 selected from methyl, ethyl, n-propyl, isopropyl, isobutyl or tert-butyl; R 15 selected from methyl, cyclopropyl or trifluoromethyl; R 16 selected from hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl or trifluoromethyl; R 17 selected from hydrogen, fluorine, chlorine, bromine, nitro or cyano; or, the optical isomers, agriculturally acceptable salts or derivatives of the compound of formula (I).

6. The compound according to claim 5, characterized in that: In general formula (I) R1 and R2 are each independently selected from hydrogen, fluorine or chlorine; R3 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl; R4 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl or tert-butyl; R5 is selected from hydrogen, methyl, ethyl, trifluoromethyl, vinyl, allyl, propargyl, CH2SiC(CH3)3, phenyl which is unsubstituted or substituted by 1-2 groups independently selected from the following: fluorine, chlorine or bromine; R6 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxyethyl, ethoxyethyl, propoxyethyl, isopropoxyethyl, methoxypropyl, ethoxypropyl, trifluoromethyl, trifluoroethyl, difluoromethyl, difluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethylene, cyclopentylmethylene, cyclohexylmethylene, CH2CO2R7, CH(CH3)CO2R7, C(CH3)2CO2R7, CH(C2H5)CO2R7, CH2CH2CO2R7, phenyl or benzyl which is unsubstituted or substituted by 1-2 groups independently selected from the following: fluorine, chlorine or bromine; R7 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, trifluoroethyl, difluoromethyl, difluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl, allyl, propargyl, allylbutyl or propargylbutyl; Q is selected from the following Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12 or Q17; R8 is selected from trifluoromethyl, trifluoroethyl, difluoromethyl, 1,1-difluoroethyl or 2,2-difluoroethyl; R9 is selected from methyl, ethyl, n-propyl, isopropyl or NH2; R 10 selected from methyl, ethyl, n-propyl or isopropyl; R 11 selected from methyl, ethyl, isopropyl, tert-butyl, difluoromethyl, trifluoroethyl, 1,1-difluoroethyl or 2,2-difluoroethyl; R 12 selected from methyl, trifluoromethyl, difluoromethyl, methoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, trifluoroethoxy or difluoroethoxy; R 13 selected from hydrogen, chlorine, bromine or methyl; R 14 selected from methyl, ethyl, n-propyl, isopropyl, isobutyl or tert-butyl; R 16 selected from hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl or trifluoromethyl; R 17 selected from hydrogen, fluorine, chlorine, bromine, nitro or cyano; or, the optical isomers, agriculturally acceptable salts or derivatives of the compound of formula (I).

7. The compound according to claim 6, wherein: In general formula (I) R1 and R2 are each independently selected from hydrogen, fluorine or chlorine; R3 is selected from hydrogen, methyl or ethyl; R4 is selected from hydrogen or methyl; R5 is selected from hydrogen, methyl, ethyl, trifluoromethyl or vinyl; R6 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxyethyl, ethoxyethyl, trifluoromethyl, trifluoroethyl, difluoromethyl, difluoroethyl, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethylene, cyclopentylmethylene, cyclohexylmethylene, CH2CO2R7, CH(CH3)CO2R7, C(CH3)2CO2R7, CH(C2H5)CO2R7, CH2CH2CO2R7, benzyl which is unsubstituted or substituted by 1-2 groups independently selected from the following: fluorine, chlorine or bromine; R7 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, allyl or propargyl; Q is selected from the following Q1, Q2, Q3, Q4, Q9, Q11, Q12 or Q17; R8 is selected from trifluoromethyl, trifluoroethyl, difluoromethyl, 1,1-difluoroethyl or 2,2-difluoroethyl; R9 is selected from methyl or NH2; R 10 selected from methyl or ethyl; R 11 selected from methyl or difluoromethyl; R 12 selected from methyl, trifluoromethyl, difluoromethyl, isopropoxy, difluoromethoxy, trifluoroethoxy or difluoroethoxy; R 13 selected from chlorine, bromine or methyl; R 14 selected from methyl, isopropyl, isobutyl or tert-butyl; R 16 selected from trifluoromethyl; R 17 selected from hydrogen, fluorine, chlorine or bromine; or, the optical isomers, agriculturally acceptable salts or derivatives of the compound of formula (I).

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

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