Alpha-hydroxy ester compounds with an indolinocyclohexanone skeleton and use thereof

Abstract

The present application relates to the field of pesticide herbicide, disclose containing with indole and cyclohexanone as the skeleton alpha hydroxy ester compound and its application. The compound provided by the present application has the structure shown in formula I. The compound is alpha hydroxy ester compound with indole and cyclohexanone as the skeleton, as herbicide has the advantages of low toxicity and high herbicidal activity.

Description

Technical Field

[0001] This invention relates to the field of pesticides and herbicides, specifically to a class of herbicidal compounds containing α-hydroxy esters with an indolecyclohexanone skeleton and their application in the field of pesticides and herbicides. Background Technology

[0002] Branched-chain amino acids (leucine, isoleucine, and valine) are essential substances for protein synthesis in plants and are also necessary for plant growth. The biosynthetic pathways of these amino acids require three key enzymes: acetolactate synthase (ALS), acetylhydroxy acid isomerase (KARI), and dihydroxy acid dehydratase (DHAD). DHAD primarily catalyzes the dehydration of α,β-dihydroxy acids to form α-keto acids. When DHAD enzymes are inhibited, the synthesis of leucine, isoleucine, and valine in the organism is hindered, leading to the inability to synthesize a large amount of protein normally, thus severely damaging plant growth and even causing death. In recent years, the design and development of new herbicides targeting the inhibition of branched-chain amino acid biosynthesis has become an important research area. These herbicides are characterized by high activity, broad weed control spectrum, high safety for humans and animals, and environmental friendliness. Therefore, DHAD-based herbicides are a class of herbicides with significant research value and development prospects. In recent years, only one natural product, aspartic acid (AA), has been reported to have good inhibitory effects on DHAD. Based on a systematic study of DHAD targets, this invention designs and synthesizes a novel class of DHAD herbicides with an indolecyclohexanone backbone of α-hydroxy esters. Summary of the Invention

[0003] The purpose of this invention is to provide a class of α-hydroxy ester compounds containing indolecyclohexanone as the skeleton and their applications. The compounds of this invention have high herbicidal activity against broadleaf weeds and grass weeds.

[0004] To achieve the above objectives, a first aspect of the present invention provides a class of α-hydroxy ester compounds containing an indolecyclohexanone backbone, having the structure shown in Formula I: .

[0005] In Equation I, R 1 Selected from H, C1-C 12 Alkyl, C2-C6 alkenyl, C2-C6 acyl, C2-C6 alkynyl, C1-C substituted with halogen 12 Alkyl, substituted or unsubstituted phenyl, benzyl, naphthyl, pyrrolyl, furanyl, tetrahydrofuranyl, thienyl, thiazolyl, imidazolyl, pyrazolyl, oxazolyl, valproicinyl, pyridyl, pyranyl, piperidinyl, piperazinyl, pyridazinyl, pyrimidinyl, caprolactamyl, C3-C8 heterocycles;

[0006] R2 Selected from any group from X1-X6 below;

[0007] ;

[0008] Among them, A in X1-X6 1 A 2 A 3a A 3b A 4 A 5 A 6a A 6b Each of the following is independently selected from H, C1-C8 alkyl, halogen-substituted C1-C8 alkyl, phenyl, benzyl, naphthyl, pyridyl, furanyl, thiophene, pyrazolyl, imidazolyl, phenyl, benzyl, naphthyl, pyridyl, furanyl, thiophene, pyrazolyl, imidazolyl, and C3-C8 heterocycles substituted with C1-C8 alkyl and / or halogens;

[0009] R 3 Selected from H, C1-C 12 Alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C substituted with halogen 12 Alkyl, substituted or unsubstituted phenyl, benzyl, naphthyl, pyrrolyl, furanyl, tetrahydrofuranyl, thienyl, thiazolyl, imidazolyl, pyrazolyl, oxazolyl, valproicinyl, pyridyl, pyranyl, piperidinyl, piperazinyl, pyridazinyl, pyrimidinyl, caprolactamyl, C3-C8 heterocycles;

[0010] R 4 Selected from H, halogens, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, substituted or unsubstituted phenyl, substituted or unsubstituted phenoxy, benzyl, substituted or unsubstituted benzyloxy, naphthyl, pyrroleyl, furanyl, tetrahydrofuranyl, thienyl, thiazolyl, imidazolyl, pyrazolyl, oxazolyl, valeronyl, pyridyl, pyranyl, piperidinyl, piperazinyl, pyridazinyl, pyrimidinyl, caprolactamyl, C3-C8 heterocycles;

[0011] And R 1 R 3 Or R 4 The optional substituents present in the n are each independently selected from halogens, C1-C6 alkyl groups, C1-C6 alkoxy groups, C1-C6 alkyl groups substituted with halogens, C1-C6 alkoxy groups substituted with halogens, phenoxy groups, nitro groups, cyano groups, and amino groups; n = 1, 2, 3, 4, 5, 6.

[0012] Preferably, in the compound,

[0013] R 1 Selected from H, or CH2R 5 , where R 5 Selected from H, C1-C3 alkyl, C5-C6 cycloalkyl, C2-C5 alkenyl, C2-C5 alkynyl, halogen-substituted C1-C6 alkyl, or halogen-substituted C1-C3 alkyl, cyano, C1-C3 alkoxy, halogen-substituted C1-C6 alkoxy, nitro-substituted or unsubstituted phenyl, naphthyl;

[0014] R 2 Any group selected from X1-X6, wherein, among X1-X6, A 1 A 2 A 3a A 3b A 4 A 5 A 6a A 6b Each of the following is independently selected from H, C1-C4 alkyl chains, C1-C4 alkyl chains substituted with one or more halogens, phenyl groups substituted with or unsubstituted with C1-C3 alkyl chains and / or amino groups and / or halogens, and benzyl groups;

[0015] R 3 Selected from H, C1-C8 alkyl, C2-C4 alkenyl, C2-C6 alkynyl, and halogen-substituted C1-C 12 Alkyl, C1-C3 alkyl and / or halogen and / or cyano and / or C1-C3 alkoxy and / or halogen-substituted C1-C3 alkyl and / or amino-substituted or unsubstituted phenyl, benzyl, naphthyl;

[0016] R 4 Selected from H, C1-C8 alkyl, C2-C4 alkenyl, C2-C6 alkynyl, halogen-substituted C1-C12 alkyl, C1-C3 alkyl and / or halogen and / or cyano and / or C1-C3 alkoxy and / or halogen-substituted C1-C3 alkyl and / or amino-substituted or unsubstituted phenyl, benzyl, naphthyl;

[0017] n = 1, 2, 3, 4.

[0018] More preferably, in the compound,

[0019] R 1 Selected from -CH2-C6H5, -CH3, -COCH3, -CH2CH=C(CH3)2, -CH2-3,5-2F-C6H3, -CH2-4-CF3-C6H4, -CH2-2-C≡N-C6H4, -CH2-C6H 11, -CH2CH=CH2, -CH2-3,5-2OCH3-C6H3, -CH2CH2CH3, -CH2-2-CF3-C6H4, -CH2-2,6-2F-C6H3, -CH2-2-F-3-CF2OCH3-C6H3, -CH2-2 -Br-C6H4, -CH2-2-F-C6H4, -CH2-2-Cl-C6H4, -CH2-2,6-2Cl-C6H3, -CH2-3,4,5-3F-C6H2, -CH2-C5H9, -CH2-4-NO2-C6H4, -CH2-C 10 Any one of H7;

[0020] R 2 Selected from -COOCH3, -COOC(CH3)3, -COOCH2C6H5, -COO(CH2)3C6H5, -COOCH2CHF2, -COOCH2CF3, -COONHNH -4-CH3-C6H5, -COONHNH-4-F-C6H5, -COOSO2C6H5, -COOSO2-4-CH3-C6H5, -COOSO2-4-F-C6H5, -CO Any one of NHSO2-4-CH3-C6H5, -CONHSO2-4-F-C6H5, -CONC3H6, -CON-3-OCH3-C3H5, -CON-3-F-C3H5, -CONC4H8, -CONHCH2C6H5, -CONHC6H5, -CONHCH2CH3, -CONHCH2-4-F-C6H4, and -CONHCH2-4-CH3-C6H4;

[0021] R 3 Selected from -H, -CH3, -CH2CH3, -CH2CH2CH 3、 -CH2-C6H5, -CH2CH=C(CH3)2, -CH2-3,5-2CH3-C6H3, -CH2-3,5-2F-C6H3, -CH2-4-CF3-C6H4, -CH2-2-C≡N-C6H4, -CH2-C6H 11 , -CH2CH=CH2, -CH2-4-F-C6H4, -CH2-3,5-2OCH3-C6H3, -CH2-2-CF3-C6H4, -CH2-2,6-2 F-C6H3, -CH2-2-Br-C6H4, -CH2-2-F-C6H4, -CH2-2-Cl-C6H4, -CH2-4-CH(CH3)2-C6H4, R 3 -CH2-3,4,5-3F-C6H2, -CH2-C5H9, -CH2-4-NO2-C6H4, -CH2-C10 H7.

[0022] R 4 Selected from -H, -F, -Cl, -Br, -I, -CH2-C6H5, -CH3, -CH2CH=C(CH3)2, -CH2-3,5-2F-C6H3, -CH2-4-CF3-C6H4, -CH2-2-C≡N-C6H4, -CH2-C6H 11 , -CH2CH=CH2, -CH2-3,5-2OCH3-C6H3, -CH2CH2CH3, -CH2-2-CF3-C6H4, -CH2-2,6-2F-C6H3, -CH2-2-F-3-CF2OCH3-C6H3, -CH2-2 -Br-C6H4, -CH2-2-F-C6H4, -CH2-2-Cl-C6H4, -CH2-2,6-2Cl-C6H3, -CH2-3,4,5-3F-C6H2, -CH2-C5H9, -CH2-4-NO2-C6H4, -CH2-C 10 H7, -OCH3, -OCH2C6H5, -OCH2-3,5-2F-C6H3, -OCH2-4-CF3-C6H4, -OCH2-2-C≡N-C6H4, -OCH2-C6H 11 , -OCH2CH=CH2, -OCH2-3,5-2OCH3-C6H3, -OCH2CH2CH3, -OCH2-2-CF3-C6H4, -OCH2-2,6-2F-C6H3, -OCH2-2-F-3-CF2OCH3-C6H3, -OCH2-2 -Br-C6H4, -OCH2-2-F-C6H4, -OCH2-2-Cl-C6H4, -OCH2-2,6-2Cl-C6H3, -OCH2-3,4,5-3F-C6H2, -OCH2-C5H9, -OCH2-4-NO2-C6H4, -OCH2-C 10 Any one of H7;

[0023] More preferably, in the compound,

[0024] R 1Selected from any one of -CH2-C6H5, -CH2-3,5-2F-C6H3, -CH2-4-CF3-C6H4, -CH2-2-C≡N-C6H4, -CH2-3,5-2OCH3-C6H3, -CH2CH2CH3, -CH2-2-CF3-C6H4, -CH2-2,6-2F-C6H3, -CH2-2-F-3-CF2OCH3-C6H3, -CH2-2-Br-C6H4, -CH2-2-F-C6H4, -CH2-2-Cl-C6H4, -CH2-2,6-2Cl-C6H3;

[0025] R 2 Selected from any one of -COOCH3, -COOCH2C6H5, -COONHNH-4-CH3-C6H5, -COOSO2C6H5, -CONC4H8, and -CONHCH2CH3;

[0026] R 3 It is selected from any one of -H, -CH3, and -CH2CH=C(CH3)2.

[0027] R 4 It is selected from any one of -H, -CH3, -F, and -OCH3.

[0028] More preferably, the α-hydroxy ester compound of the present invention with indolecyclohexanone as its backbone is specifically:

[0029] Compound K1: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0030] Compound K2: R 1 -CH2-3,5-2CH3-C6H3, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0031] Compound K3: R 1 For -CH2-2-Cl-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0032] Compound K4: R 1 -CH2-2,6-2F-C6H3, R 2 For -COOCH3, R 3 -H, R4 -H;

[0033] Compound K5: R 1 For -CH2-2-I-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0034] Compound K6: R 1 For -CH2-2-Br-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0035] Compound K7: R 1 The value is -CH2-2,6-2Cl-C6H3, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0036] Compound K8: R 1 For -CH2CH3, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0037] Compound K9: R 1 For -CH3, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0038] Compound K10: R 1 -CH2-3,5-2OCH3-C6H3, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0039] Compound K11: R 1 For -CH2CH2CH3, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0040] Compound K12: R 1 For -CH2-3-Cl-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0041] Compound K13: R 1 It is -CH2-4-F-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0042] Compound K14: R 1 -CH2-3,5-2F-4-OCH3-C6H3, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0043] Compound K15: R 1 For -CH2-C6H5, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0044] Compound K16: R 1 For -CH2CH=CH2, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0045] Compound K17: R 1 For -CH2CH=C(CH3)2, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0046] Compound K18: R 1 -CH2-3,5-2F-C6H3, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0047] Compound K19: R 1 For -CH2-4-CF3-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0048] Compound K20:R 1 For -CH2-2-C≡N-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0049] Compound K21: R 1-CH2-C6H 11 R 2 For -COOCH3, R 3 -H, R 4 -H;

[0050] Compound K22: R 1 For -CH2-2-CF3-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0051] Compound K23: R 1 The value is -CH2-4-CH(CH3)2-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0052] Compound K24: R 1 -CH2-3,4,5-3F-C6H2, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0053] Compound K25: R 1 For -CH2-C5H9, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0054] Compound K26: R 1 For -CH2-4-NO2-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0055] Compound K27: R 1 -CH2-C 10 H7, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0056] Compound K28: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH2C6H5, R 3 -H, R 4 -H;

[0057] Compound K29: R 1For -CH2-2-F-C6H4, R 2 For -COOC(CH3)3, R 3 -H, R 4 -H;

[0058] Compound K30: R 1 For -CH2-2-F-C6H4, R 2 -COO(CH2)3C6H5, R 3 -H, R 4 -H;

[0059] Compound K31: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH2CHF2, R 3 -H, R 4 -H;

[0060] Compound K32: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH2CF3, R 3 -H, R 4 -H;

[0061] Compound K33: R 1 For -CH2-2-F-C6H4, R 2 -COONHNH-4-CH3-C6H5, R 3 -H, R 4 -H;

[0062] Compound K34: R 1 For -CH2-2-F-C6H4, R 2 For -COONHNH-4-F-C6H5, R 3 -H, R 4 -H;

[0063] Compound K35: R 1 For -CH2-2-F-C6H4, R 2 For -COOSO2C6H5, R 3 -H, R 4 -H;

[0064] Compound K36: R 1 For -CH2-2-F-C6H4, R 2 For -COOSO2-4-CH3-C6H5, R 3 -H, R 4 -H;

[0065] Compound K37: R 1 For -CH2-2-F-C6H4, R 2 For -COOSO2-4-F-C6H5, R 3 -H, R 4 -H;

[0066] Compound K38: R 1 For -CH2-2-F-C6H4, R 2 For -CONHSO2C6H5, R 3 -H, R 4 -H;

[0067] Compound K39: R 1 For -CH2-2-F-C6H4, R 2 For -CONHSO2-4-CH3-C6H5, R 3 -H, R 4 -H;

[0068] Compound K40: R 1 For -CH2-2-F-C6H4, R 2 For -CONHSO2-4-F-C6H5, R 3 -H, R 4 -H;

[0069] Compound K41: R 1 For -CH2-2-F-C6H4, R 2 For -CONC3H6, R 3 -H, R 4 -H;

[0070] Compound K42: R 1 For -CH2-2-F-C6H4, R 2 For -CON-3-OCH3-C3H5, R 3 -H, R 4 -H;

[0071] Compound K43: R 1 For -CH2-2-F-C6H4, R 2 For -CON-3-F-C3H5, R 3 -H, R 4 -H;

[0072] Compound K44: R 1 For -CH2-2-F-C6H4, R 2 For -CONC4H8, R 3 -H, R 4 -H;

[0073] Compound K45: R 1 For -CH2-2-F-C6H4, R 2 For -CONHCH2C6H5, R 3 -H, R 4 -H;

[0074] Compound K46: R 1 For -CH2-2-F-C6H4, R 2 For -CONHC6H5, R 3 -H, R 4 -H;

[0075] Compound K47: R 1 For -CH2-2-F-C6H4, R 2 For -CONHCH2CH3, R 3 -H, R 4 -H;

[0076] Compound K48: R 1 For -CH2-2-F-C6H4, R 2 For -CONHCH2-4-F-C6H4, R 3 -H, R 4 -H;

[0077] Compound K49: R 1 For -CH2-2-F-C6H4, R 2 For -CONHCH2-4-CH3-C6H4, R 3 -H, R 4 -H;

[0078] Compound K50: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH3, R 4 -H;

[0079] Compound K51: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2CH3, R 4 -H;

[0080] Compound K52: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2-C6H5, R4 -H;

[0081] Compound K53: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2CH=C(CH3)2, R 4 -H;

[0082] Compound K54: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 -CH2-3,5-2CH3-C6H3, R 4 -H;

[0083] Compound K55: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 -CH2-3,5-2F-C6H, R 4 -H3;

[0084] Compound K56: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2-4-CF3-C6H4, R 4 -H;

[0085] Compound K57: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2-2-C≡N-C6H4, R 4 -H;

[0086] Compound K58: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 -CH2-C6H 11 R 4 -H;

[0087] Compound K59: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2CH=CH2, R 4 -H;

[0088] Compound K60: R1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 It is -CH2-4-F-C6H4, R 4 -H;

[0089] Compound K61: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 -CH2-3,5-2OCH3-C6H3, R 4 -H;

[0090] Compound K62: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2CH2CH3, R 4 -H;

[0091] Compound K63: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2-2-CF3-C6H4, R 4 -H;

[0092] Compound K64: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 -CH2-2,6-2F-C6H3, R 4 -H;

[0093] Compound K65: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2-2-Br-C6H4, R 4 -H;

[0094] Compound K66: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2-2-F-C6H4, R 4 -H;

[0095] Compound K67: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3For -CH2-2-Cl-C6H4, R 4 -H;

[0096] Compound K68: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 The value is -CH2-4-CH(CH3)2-C6H4, R 4 -H;

[0097] Compound K69: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 -CH2-3,4,5-3F-C6H2, R 4 -H;

[0098] Compound K70: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2-C5H9, R 4 -H;

[0099] Compound K71: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2-4-NO2-C6H4, R 4 -H;

[0100] Compound K72: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 -CH2-C 10 H7, R 4 It is -H.

[0101] Compound K73: R 1 -CH2-2,4-2F-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0102] Compound K74: R 1 For -CH(CH3)2, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0103] Compound K75: R 1For -CH2-4-OCH3-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0104] Compound K76: R 1 For -CH2-3-F-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0105] Compound K77: R 1 For -CH2-2-CH3-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0106] Compound K78: R 1 For -CH2-3-OCH3-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0107] Compound K79: R 1 For -CH2-C4H7, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0108] Compound K80: R 1 For -CH2OCH3, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0109] Compound K81: R 1 For -CH2-C3H5, R 2 For -COOCH3, R 3 -H, R 4 -H;

[0110] Compound K82: R 1 For -CH3, R 2 For -COOCH3, R 3 -H, R 4 -6-F;

[0111] Compound K83: R 1 For -CH2CH3, R 2 For -COOCH3, R 3-H, R 4 -6-F;

[0112] Compound K84: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -6-F;

[0113] Compound K85: R 1 For -COCH3, R 2 For -COOCH3, R 3 -H, R 4 It is -6-F.

[0114] Compound K86: R 1 For -CH2-2-F-C6H4, R 2 For -COCH3, R 3 -H, R 4 It is -H.

[0115] Compound K87: R 1 For -CH2-2-F-C6H4, R 2 For -COCH2CH3, R 3 -H, R 4 It is -H.

[0116] Compound K88: R 1 For -CH2-2-F-C6H4, R 2 For -COC6H4, R 3 -H, R 4 It is -H.

[0117] Compound K89: R 1 For -CH3, R 2 For -COOCH3, R 3 -H, R 4 It is -7-F.

[0118] Compound K90: R 1 For -CH3, R 2 For -COOCH3, R 3 -H, R 4 It is -6-CH3.

[0119] Compound K91:R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 -H, R 4 It is -6-CH3.

[0120] Compound K92: R 1 For -CH2CH3, R 2 For -COOCH3, R 3 -H, R 4 It is -6-OCH3.

[0121] Compound K93: R 1 For -CH3, R 2 For -COOCH3, R 3 -H, R 4 It is -6-OCH3.

[0122] Compound K94:R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 -H, R 4 It is -6-OCH3.

[0123] This invention also provides a method for synthesizing the α-hydroxy ester compound of this invention, comprising an indolecyclohexanone backbone, using the following route:

[0124] Route 1: .

[0125] Route 2: .

[0126] Route 3: .

[0127] The substituents in the synthetic route are defined in the same way as the corresponding groups in formula (I) of this invention;

[0128] In step A, the synthesis method of formula I-2 is as follows: 10 mmol of substituted phenylhydrazine hydrochloride is added to a 250 mL round-bottom flask containing 100 mL of anhydrous acetic acid, and the mixture is heated to reflux and stirred. Initial raw material I-1 (10 mmol) is slowly added dropwise to the reaction system. After the addition is complete, the reaction system is stirred for 2 h under reflux conditions. The reaction is monitored by TLC. After the reaction is complete, 30 mL of water is added to quench the reaction system. After the reaction system cools to room temperature, it is poured into 150 g of ice water, and 150 mL of ethyl acetate is added for extraction. The organic phase is washed three times with 200 mL of saturated brine. The organic layers are combined, dried, concentrated, and then subjected to column chromatography to obtain intermediate I-2.

[0129] In step B, the synthesis of formula I-3 is as follows: intermediate I-2 (1 mmol) is dissolved in anhydrous tetrahydrofuran (15 mL), and NaH (4 mmol) is added under ice bath conditions. After the reaction system stabilizes, the halogenated product (2 mmol) is added, and the mixture is stirred at room temperature until the reaction is complete as monitored by TLC. NaH is quenched by adding ice water to the reaction system, tetrahydrofuran is removed by vacuum distillation, and the mixture is extracted three times with ethyl acetate (15 mL). The organic layers are combined, and the organic phase is washed three times with saturated sodium chloride solution (100 mL). After drying and concentration, column chromatography is performed to obtain intermediate I-3 of a series of compounds.

[0130] In step C, the synthesis method of formula I-4 is as follows: Intermediate I-3 (1 mmol) of the series of compounds is dissolved in anhydrous tetrahydrofuran (5 mL). Under ice bath conditions, it is slowly added to a 10 mL Schlenk flask containing NaH (5 mmol) using a 10 mL syringe. The entire reaction system is carried out under nitrogen protection. After the reaction system stabilizes, the temperature of the reaction system is increased to 70 °C, and DMC (10 mmol) is slowly added to the reaction system using a 1 mL syringe. The mixture is stirred at 70 °C until the reaction is complete as monitored by TLC. NaH is quenched by adding ice water to the reaction system, tetrahydrofuran is removed by vacuum distillation, and the mixture is extracted three times with ethyl acetate (15 mL). The organic layers are combined, and the organic phase is washed three times with saturated sodium chloride solution (100 mL). After drying and concentration, column chromatography is performed to obtain intermediate I-4 of the series of compounds.

[0131] In step D, the synthesis of formula I-5 is as follows: intermediate II-4 (1 mmol) of the series of compounds is dissolved in DMF (10 mL), followed by the addition of Cs2CO3 (1.5 mmol). The reaction is monitored by TLC until completion. The reaction is terminated by adding water to the reaction system, and the mixture is extracted three times with ethyl acetate (15 mL). The organic layers are combined, washed three times with saturated brine (100 mL), dried and concentrated, and then subjected to column chromatography to obtain the series of target compounds I-5.

[0132] In step E, the synthesis method of formula II-1 is as follows: dissolve the intermediate of formula I-4 in a solvent, add sodium hydroxide solution dropwise, stir at room temperature, and after the reaction is complete, remove the organic solvent, acidify with 2N hydrochloric acid to pH=1.5-2.5, precipitate a solid, filter and dry to obtain intermediate of formula II-1.

[0133] In step F, the synthesis method of formula II-2 is as follows: dissolve raw material II-1 in a solvent, add oxaloyl chloride dropwise, stir the reaction at -5℃ to 5℃, and after the reaction is completed, remove the solvent and the remaining solid is the intermediate of formula II-2.

[0134] In step G, the synthesis method of formula II-3 is as follows: at 0-5℃, an alcoholic raw material, an amine raw material, a sulfonic acid, a sulfonamide, or a cyclic amine intermediate is dissolved in a solvent, and triethylamine is added and stirred. Then, the solution of intermediate II-2 dissolved in the solvent is added dropwise to the above reaction system. After the reaction is completed, a saturated sodium bicarbonate solution is added to the reaction system, the organic layers are extracted and combined, dried and concentrated, and column chromatography is performed to obtain intermediate II-3.

[0135] In step H, the synthesis method of formula II-4 is as follows: intermediate II-3 and Cs2CO3 are dissolved in a solvent, stirred at room temperature under aerobic conditions, and after the reaction is completed, the mixture is extracted, washed with saturated brine, the organic layers are combined, dried and concentrated by column chromatography to obtain formula II-4.

[0136] In step I, the synthesis method of formula III is as follows: dissolve formula I-5 and K2CO3 in a solvent, add the halogenated product, stir at room temperature, and after the reaction is complete, extract, wash with saturated brine, combine the organic layers, dry and concentrate, and precipitate formula III by column chromatography.

[0137] The present invention will be described in detail below through examples. In the following examples, unless otherwise specified, all raw materials used are commercially available. The terminology of the present invention is explained below.

[0138] “C1-C 12 "alkyl" refers to an alkyl group with a total number of carbon atoms of 1-12, including straight-chain alkyl, branched alkyl, or cycloalkyl. For example, it can be a straight-chain alkyl, branched alkyl, or cycloalkyl group with a total number of carbon atoms of 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12. Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, cyclopropyl, methylcyclopropyl, ethylcyclopropyl, cyclobutyl, methylcyclobutyl, ethylcyclobutyl, cyclopentyl, methylcyclopentyl, ethylcyclopentyl, cyclohexyl, methylcyclohexyl, ethylcyclohexyl, etc.

[0139] In this invention, "C1-C" 12 "alkoxy group" refers to an alkoxy group with 1-12 carbon atoms, such as methyloxy, ethyloxy, n-propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, tert-butyloxy, n-pentyloxy, isopentyloxy, n-hexyloxy, cyclopropyloxy, methylcyclopropyloxy, ethylcyclopropyloxy, cyclopentyloxy, methylcyclopentyloxy, and cyclohexyloxy.

[0140] In this invention, "C1-C" 12 "Alkylamino" indicates an amino group with alkyl-substituted carbon atoms of 1-12, which can be mono- or dialkyl-substituted, wherein the alkyl group can be the same and / or different when dialkyl-substituted.

[0141] In this invention, "C1-C" 12 "Alkyl mercapto" indicates an alkyl mercapto group with 1-12 carbon atoms, such as methyl mercapto, ethyl mercapto, n-propyl mercapto, isopropyl mercapto, n-butyl mercapto, isobutyl mercapto, tert-butyl mercapto, n-pentyl mercapto, isopentyl mercapto, n-hexyl mercapto, cyclopropyl mercapto, methylcyclopropyl mercapto, ethylcyclopropyl mercapto, cyclopentyl mercapto, methylcyclopentyl mercapto, cyclohexyl mercapto, etc.

[0142] In this invention, "C2-C6 alkenyl" refers to a monoalkenyl, dienyl, or polyalkenyl group having 1-6 carbon atoms, such as vinyl, n-propenyl, isopropenyl, n-butenyl, n-dibutenyl, isobutenyl, tert-butenyl, n-pentenyl, 1,3-pentadienyl, isopentenyl, n-hexenyl, 1,3-hexadienyl, cyclopropenyl, methylcyclopropenyl, ethylcyclopropenyl, cyclopentenyl, methylcyclopentenyl, and cyclohexenyl.

[0143] In this invention, "C2-C6 alkynyl" refers to a mono-alkynyl, di-alkynyl, or poly-alkynyl group having 1-6 carbon atoms. Examples include ethynyl, n-propynyl, isopropynyl, n-butynyl, n-dibutynyl, isobutynyl, tert-butynyl, n-pentynyl, 1,3-pentadiynyl, isopentenynyl, n-hexynyl, 1,3-hexadiynyl, cyclopropynyl, methylcyclopropynyl, ethylcyclopropynyl, cyclopentynyl, methylcyclopentynyl, and cyclohexynyl.

[0144] In this invention, the term "substituted or unsubstituted C3-C8 heterocycle" refers to a heterocycle containing at least one of N, O, and S.

[0145] In this invention, "halogen" means at least one element selected from fluorine, chlorine, bromine and iodine.

[0146] The present invention does not particularly limit the method for synthesizing the α-hydroxy ester compound containing indolecyclohexanone as the skeleton shown in formula (I). Those skilled in the art can obtain suitable methods for preparing the derivatives shown in formula (I) by combining the compound structure provided by the present invention with the synthesis methods in the field of chemistry. The present invention will not elaborate on these methods here.

[0147] A second aspect of the present invention provides the use of the aforementioned first aspect of α-hydroxy ester compounds containing an indolecyclohexanone backbone in inhibiting dihydroxy acid dehydratase (DHAD), a target in weeds.

[0148] The third aspect of the present invention provides the application of the aforementioned first aspect containing α-hydroxy ester compounds with an indolecyclohexanone skeleton in the control of weeds. The weeds include foxtail grass, barnyard grass, Echinochloa crus-galli, crabgrass, jointed goatgrass, wild oats, wild oats, Japanese wild oats, ryegrass, wild oats, cassia, morning glory, cocklebur, sedge, vetch, amaranth, false groundcherry, angelica sinensis, purslane, spiny amaranth, beggar-ticks, double-spike barnyard grass, rice grass, water bamboo leaf, wild arrowhead, water plantain, water lily, water lily, dayflower, duckweed, fireweed, sedge, etc., more specifically foxtail grass, barnyard grass, angelica sinensis, and amaranth.

[0149] Preferably, the present invention provides the application of the aforementioned first aspect of α-hydroxy ester compounds containing indolecyclohexanone as the backbone in the control of broadleaf weeds, grass weeds, and / or sedge weeds.

[0150] More preferably, in this invention, the broadleaf weeds include amaranth, lamb's quarters, velvetleaf, rice-leaf grass, cassia seed, morning glory, cocklebur, reverse-branch amaranth, false groundcherry, angelica sinensis, purslane, spiny amaranth, water bamboo leaf, wild arrowhead, water plantain, rain-flower, dayflower, duck tongue grass, etc.

[0151] More preferably, in this invention, the grassy weeds include foxtail grass, barnyard grass, barnyard grass, crabgrass, jointed goatgrass, wild oat, wild oat, Japanese wild oat, amaranth, lambsquarters, and reverse-branch amaranth.

[0152] A fourth aspect of the present invention provides the application of the aforementioned first aspect of using an α-hydroxy ester compound with an indolecyclohexanone backbone as an active ingredient in the preparation of a pesticide herbicide. The weeds targeted by the pesticide herbicide are as described in the third aspect.

[0153] A fifth aspect of the present invention provides a pesticide herbicide, wherein the active ingredient in the pesticide herbicide includes at least one of the α-hydroxy ester compounds containing an indolecyclohexanone skeleton as described in the first aspect above.

[0154] Preferably, the herbicide is composed of an active ingredient and excipients, wherein the content of the active ingredient is 1-99.9999% by weight.

[0155] More preferably, the content of the active ingredient is 1-50% by weight. The formulation of the pesticide herbicide can be emulsifiable concentrate, suspension concentrate, wettable powder, powder, granule, aqueous solution, poison bait, mother liquor or mother powder, etc., whichever is required by the reagent.

[0156] This invention has the following advantages:

[0157] First, the herbicides of this invention exhibit a novel mode of action. Containing α-hydroxy ester compounds with an indolecyclohexanone backbone, they act on dihydroxy acid dehydrating enzyme (DHAD), a target currently untested and unmarketed. This invention demonstrates high herbicidal activity; the α-hydroxy ester compounds with an indolecyclohexanone backbone exhibit strong inhibitory effects on weeds, with some compounds showing comparable inhibitory effects to penflusulfonium and bispyribac-sodium, indicating significant application value.

[0158] Secondly, the compounds of this invention have simple structures and are easy to prepare. The α-hydroxy ester compounds of this invention, containing an indolecyclohexanone backbone, have simple chemical formulas and are easy to prepare. Furthermore, as herbicides, the compounds of this invention are safe for mammals. The α-hydroxy ester compounds with an indolecyclohexanone backbone are herbicides designed to target the branched-chain amino acid biosynthesis pathway, which exists only in plants and some microorganisms, thus ensuring safety for mammals. Detailed Implementation

[0159] The present invention will be further described in detail below with reference to the embodiments. Reagents or instruments used without a specified manufacturer are considered to be conventional products that can be purchased on the market.

[0160] Example 1: Synthesis of Compound I-2

[0161]

[0162] 10 mmol of substituted phenylhydrazine hydrochloride was added to a 250 mL round-bottom flask containing 100 mL of anhydrous acetic acid, and the mixture was heated to reflux and stirred. Initial reactant II-1 (10 mmol) was slowly added to the reaction system. After the addition was complete, the reaction system was stirred under reflux for 2 h, and the reaction was monitored by TLC. After the reaction was complete, 30 mL of water was added to quench the reaction system. After the reaction system cooled to room temperature, it was poured into 150 g of ice water, and extracted with 150 mL of ethyl acetate. The organic phase was washed three times with 200 mL of saturated brine, and the organic layers were combined. The organic phase was dried, concentrated, and subjected to column chromatography to obtain intermediate I-2.

[0163] Example 2: Synthesis of compound K1

[0164]

[0165] The synthesis method of Formula I-3a is as follows: Intermediate I-2a (1 mmol) was dissolved in anhydrous tetrahydrofuran (15 mL), and NaH (4 mmol) was added under ice bath conditions. After the reaction system stabilized, o-fluorobenzyl bromide (2 mmol) was added, and the mixture was stirred at room temperature until the reaction was complete as monitored by TLC. NaH was quenched by adding ice water to the reaction system, tetrahydrofuran was removed by vacuum distillation, and the mixture was extracted three times with ethyl acetate (15 mL). The organic layers were combined, and the organic phase was washed three times with saturated sodium chloride solution (100 mL). After drying and concentration, column chromatography was performed to obtain a series of intermediates I-3a.

[0166] The synthesis method of Formula I-4a is as follows: Intermediate I-3a (1 mmol) of the series of compounds was dissolved in anhydrous tetrahydrofuran (5 mL). Under ice bath conditions, it was slowly added to a 10 mL Schlenk flask containing NaH (5 mmol) using a 10 mL syringe. The entire reaction system was carried out under nitrogen protection. After the reaction system stabilized, the temperature of the reaction system was increased to 70 °C, and DMC (10 mmol) was slowly added to the reaction system using a 1 mL syringe. The mixture was stirred at 70 °C until the reaction was complete as monitored by TLC. NaH was removed by adding ice water to the reaction system, tetrahydrofuran was removed by vacuum distillation, and the mixture was extracted three times with ethyl acetate (15 mL). The organic layers were combined, and the organic phase was washed three times with saturated sodium chloride solution (100 mL). After drying and concentration, column chromatography was performed to obtain intermediate I-4a of the series of compounds.

[0167] The synthesis of K1 was performed as follows: intermediate I-4a (1 mmol) was dissolved in DMF (10 mL), followed by the addition of Cs₂CO₃ (1.5 mmol). The reaction was monitored by TLC until completion. The reaction was terminated by adding water to the reaction system, and the mixture was extracted three times with ethyl acetate (15 mL). The organic layers were combined, washed three times with saturated brine (100 mL), dried, concentrated, and then subjected to column chromatography to obtain the target compound K1.

[0168] Example 3: Synthesis of compound K2

[0169]

[0170] The synthesis method of Formula I-3b is as follows: Intermediate I-2a (1 mmol) was dissolved in anhydrous tetrahydrofuran (15 mL), and NaH (4 mmol) was added under ice bath conditions. After the reaction system stabilized, m-dimethylbenzyl bromide (2 mmol) was added, and the mixture was stirred at room temperature until the reaction was complete as monitored by TLC. NaH was extracted into the reaction system with ice water, tetrahydrofuran was removed by vacuum distillation, and the mixture was extracted three times with ethyl acetate (15 mL). The organic layers were combined, and the organic phase was washed three times with saturated sodium chloride solution (100 mL). After drying and concentration, column chromatography was performed to obtain intermediate I-3b of a series of compounds.

[0171] The synthesis method of Formula I-4b is as follows: Intermediate I-3b (1 mmol) of the series of compounds was dissolved in anhydrous tetrahydrofuran (5 mL). Under ice bath conditions, it was slowly added to a 10 mL Schlenk flask containing NaH (5 mmol) using a 10 mL syringe. The entire reaction system was carried out under nitrogen protection. After the reaction system stabilized, the temperature of the reaction system was increased to 70 °C, and DMC (10 mmol) was slowly added to the reaction system using a 1 mL syringe. The mixture was stirred at 70 °C until the reaction was complete as monitored by TLC. NaH was quenched by adding ice water to the reaction system, tetrahydrofuran was removed by vacuum distillation, and the mixture was extracted three times with ethyl acetate (15 mL). The organic layers were combined, and the organic phase was washed three times with saturated sodium chloride solution (100 mL). After drying and concentration, column chromatography was performed to obtain intermediate I-4b of the series of compounds.

[0172] The synthesis of K2 was performed as follows: intermediate I-4b (1 mmol) was dissolved in DMF (10 mL), followed by the addition of Cs2CO3 (1.5 mmol). The reaction was monitored by TLC until completion. The reaction was terminated by adding water to the reaction system, and the mixture was extracted three times with ethyl acetate (15 mL). The organic layers were combined, washed three times with saturated brine (100 mL), dried, concentrated, and then subjected to column chromatography to obtain the target compound K3.

[0173] Example 4: Synthesis of compound K3

[0174]

[0175] The preparation of other reference compound K1 differs in that o-chlorobenzyl bromide is used to substitute the NH position of intermediate I-2.

[0176] Example 5: Synthesis of compound K4

[0177]

[0178] The preparation of other reference compounds K1 differs in that the NH position of intermediate I-2 is substituted with m-difluorobenzyl bromide.

[0179] Example 6: Synthesis of compound K5

[0180]

[0181] The preparation of other reference compounds K1 differs in that o-iodobenzyl bromide is used to substitute the NH position of intermediate I-2.

[0182] Example 7: Synthesis of compound K6

[0183]

[0184] The preparation of other reference compounds K1 differs in that o-bromobenzyl bromide is used to substitute the NH position of intermediate I-2.

[0185] Example 8: Synthesis of compound K7

[0186]

[0187] The preparation of other reference compound K1 differs in that o-dichlorobenzyl bromide is used to substitute the NH position of intermediate I-2.

[0188] Example 9: Synthesis of compound K8

[0189]

[0190] The preparation of other reference compounds K1 differs in that iodoethane is used to substitute the NH position of intermediate I-2.

[0191] Example 10: Synthesis of compound K9

[0192]

[0193] The preparation of other reference compound K1 differs in that iodomethane is used to substitute the NH position of intermediate I-2.

[0194] Example 11: Synthesis of compound K10

[0195]

[0196] The preparation of other reference compounds K1 differs in that m-dimethylbenzyl bromide is used to substitute the NH position of intermediate I-2.

[0197] Example 12: Synthesis of compound K11

[0198]

[0199] The preparation of other reference compounds K1 differs in that iodopropane is used to substitute the NH position of intermediate I-2.

[0200] Example 13: Synthesis of compound K12

[0201]

[0202] The preparation of other reference compound K1 differs in that m-chlorobenzyl bromide is used to substitute the NH position of intermediate I-2.

[0203] Example 14: Synthesis of compound K13

[0204]

[0205] The preparation of other reference compound K1 differs in that p-fluorobenzyl bromide is used to substitute the NH position of intermediate I-2.

[0206] Example 15: Synthesis of compound K14

[0207]

[0208] The preparation of other reference compound K1 differs in that 3,5-difluorobenzyl bromide is used to substitute the NH position of intermediate I-2.

[0209] Example 16: Synthesis of compound K15

[0210]

[0211] The preparation of other reference compound K1 differs in that benzyl bromide is used to substitute the NH position of intermediate I-2.

[0212] Example 17: Synthesis of compound K16

[0213]

[0214] The preparation of other reference compound K1 differs in that it uses bromopropene to substitute the NH position of intermediate I-2.

[0215] Example 18: Synthesis of compound K17

[0216]

[0217] The preparation of other reference compound K1 differs in that 1-bromo-2-methyldibutene is used to substitute the NH position of intermediate I-2.

[0218] Example 19: Synthesis of compound K18

[0219]

[0220] The preparation of other reference compound K1 differs in that 3,5-difluorobenzyl bromide is used to substitute the NH position of intermediate I-2.

[0221] Example 20: Synthesis of compound K19

[0222]

[0223] The preparation of other reference compounds K1 differs in that p-trifluoromethylbenzyl bromide is used to substitute the NH position of intermediate I-2.

[0224] Example 21: Synthesis of compound K20

[0225]

[0226] The preparation of other reference compounds K1 differs in that o-cyanobenzyl bromide is used to substitute the NH position of intermediate I-2.

[0227] Example 22: Synthesis of compound K21

[0228]

[0229] The preparation of other reference compounds K1 differs in that bromomethylcyclohexane is used to substitute the NH position of intermediate I-2.

[0230] Example 23: Synthesis of compound K22

[0231]

[0232] The preparation of other reference compounds K1 differs in that o-trifluoromethylbenzyl bromide is used to substitute the NH position of intermediate I-2.

[0233] Example 24: Synthesis of compound K23

[0234]

[0235] The preparation of other reference compound K1 differs in that p-isopropylbenzyl bromide is used to substitute the NH position of intermediate I-2.

[0236] Example 25: Synthesis of compound K24

[0237]

[0238] The preparation of other reference compound K1 differs in that 3,4,5-trifluorobenzyl bromide is used to substitute the NH position of intermediate I-2.

[0239] Example 26: Synthesis of compound K25

[0240]

[0241] The preparation of other reference compounds K1 differs in that bromomethylcyclopentane is used to substitute the NH position of intermediate I-2.

[0242] Example 27: Synthesis of compound K26

[0243]

[0244] The preparation of other reference compound K1 differs in that p-nitrobenzyl bromide is used to substitute the NH position of intermediate I-2.

[0245] Example 28: Synthesis of compound K27

[0246]

[0247] The preparation of other reference compound K1 differs in that 2-bromomethylnaphthalene is used to substitute the NH position of intermediate I-2.

[0248] Example 29: Synthesis of compound K73

[0249]

[0250] The preparation of other reference compound K1 differs in that 2,4-difluorobenzyl bromide is used to substitute the NH position of intermediate I-2.

[0251] Example 30: Synthesis of compound K74

[0252]

[0253] The preparation of other reference compounds K1 differs in that isopropyl bromide is used to substitute the NH position of intermediate I-2.

[0254] Example 31: Synthesis of compound K75

[0255]

[0256] The preparation of other reference compound K1 differs in that 4-methoxybenzyl bromide is used to substitute the NH position of intermediate I-2.

[0257] Example 32: Synthesis of compound K76

[0258]

[0259] The preparation of other reference compound K1 differs in that 3-fluorobenzyl bromide is used to substitute the NH position of intermediate I-2.

[0260] Example 33: Synthesis of compound K77

[0261]

[0262] The preparation of other reference compound K1 differs in that o-methylbenzyl bromide is used to substitute the NH position of intermediate I-2.

[0263] Example 34: Synthesis of compound K78

[0264]

[0265] The preparation of other reference compound K1 differs in that 3-methoxybenzyl bromide is used to substitute the NH position of intermediate I-2.

[0266] Example 35: Synthesis of compound K79

[0267]

[0268] The preparation of other reference compound K1 differs in that bromomethylcyclobutane is used to substitute the NH position of intermediate I-2.

[0269] Example 36: Synthesis of compound K80

[0270]

[0271] The preparation of other reference compounds K1 differs in that bromomethyl methyl ether is used to substitute the NH position of intermediate I-2.

[0272] Example 37: Synthesis of compound K81

[0273]

[0274] The preparation of other reference compound K1 differs in that bromomethylcyclopropane is used to substitute the NH position of intermediate I-2.

[0275] Example 38: Synthesis of compound K82

[0276]

[0277] The preparation of other reference compound K1 differs in that iodomethane is used to substitute the NH position of intermediate I-2.

[0278] Example 39: Synthesis of compound K83

[0279]

[0280] The preparation of other reference compounds K1 differs in that iodoethane is used to substitute the NH position of intermediate I-2.

[0281] Example 40: Synthesis of compound K84

[0282]

[0283] The preparation of other reference compound K1 differs in that o-fluorobenzyl bromide is used to substitute the NH position of intermediate I-2.

[0284] Example 41: Synthesis of compound K85

[0285]

[0286] The preparation of other reference compound K1 differs in that acetyl chloride is used to substitute the NH position of intermediate I-2.

[0287] Example 42: Synthesis of compound K89

[0288]

[0289] The preparation of other reference compound K1 differs in that iodomethane is used to substitute the NH position of intermediate I-2.

[0290] Example 43: Synthesis of compound K90

[0291]

[0292] The preparation of other reference compound K1 differs in that iodomethane is used to substitute the NH position of intermediate I-2.

[0293] Example 44: Synthesis of compound K91

[0294]

[0295] The preparation of other reference compound K1 differs in that o-fluorobenzyl bromide is used to substitute the NH position of intermediate I-2.

[0296] Example 45: Synthesis of compound K92

[0297]

[0298] The preparation of other reference compounds K1 differs in that iodoethane is used to substitute the NH position of intermediate I-2.

[0299] Example 46: Synthesis of compound K93

[0300]

[0301] The preparation of other reference compound K1 differs in that iodomethane is used to substitute the NH position of intermediate I-2.

[0302] Example 47: Synthesis of compound K94

[0303]

[0304] The preparation of other reference compound K1 differs in that o-fluorobenzyl bromide is used to substitute the NH position of intermediate I-2.

[0305] Example 48: Synthesis of Compound II-2a

[0306]

[0307] Compound I-4a (1 mmol) was dissolved in 10 mL of solvent (methanol:water = 1:1). Then, sodium hydroxide (1.5 mmol) was dissolved in 2 mL of water and slowly added dropwise to the reaction system. The reaction was monitored by TLC until compound I-4a disappeared. After the reaction was complete, the methanol was removed, and the solution was acidified to pH 2 with 2N hydrochloric acid. A large amount of white solid precipitated at this point. This solid was filtered and dried to obtain product II-1a (white solid).

[0308] Compound II-1a (15 mmol) was dissolved in DCM, and oxalyl chloride (22.5 mmol) was slowly added dropwise. The reaction was stirred at -5°C to 5°C and the reaction was monitored by TLC. After the reaction was completed, the DCM was dried, and the remaining solid (white solid) was intermediate II-2a.

[0309] Example 49: Synthesis of compound K49

[0310]

[0311] At low temperature (0-5℃), 4-methylbenzylamine (2 mmol) was dissolved in DCM, and triethylamine (3 mmol) was added. After stirring for 15 min, intermediate II-2a (2.4 mmol) solution dissolved in DCM was slowly added dropwise to the reaction system. After the reaction was completed by TLC monitoring, saturated sodium bicarbonate (50 ml) solution was added to the reaction system, and the mixture was extracted three times with ethyl acetate (15 ml). The organic layers were combined, and the organic phase was washed three times with saturated brine (100 ml). The combined organic layers were extracted, dried, concentrated, and subjected to column chromatography to obtain compound II-3a (white solid).

[0312] Intermediate II-3a (1 mmol) was dissolved in DMF (10 ml), followed by the addition of Cs₂CO₃ (1.5 mmol). The reaction was monitored by TLC until completion. The reaction was terminated by adding water to the reaction system, and the mixture was extracted three times with ethyl acetate (15 ml). The organic layers were combined, washed three times with saturated brine (100 ml), dried, concentrated, and subjected to column chromatography to obtain compound K49 (white solid).

[0313] Example 50: Synthesis of compound K41

[0314]

[0315] The preparation of other reference compound K49 differs in that cyclobutamine is used to substitute the acyl chloride position of intermediate II-2a.

[0316] Example 51: Synthesis of compound K42

[0317]

[0318] The preparation of other reference compound K49 differs in that 3-methoxycyclobutane is used to substitute the acyl chloride position of intermediate II-2a.

[0319] Example 52: Synthesis of compound K43

[0320]

[0321] The preparation of other reference compound K49 differs in that 3-fluorocyclobutane is used to substitute the acyl chloride position of intermediate II-2a.

[0322] Example 53: Synthesis of compound K44

[0323]

[0324] The preparation of other reference compound K49 differs in that cyclopentylamine is used to substitute the acyl chloride position of intermediate II-2a.

[0325] Example 54: Synthesis of compound K45

[0326]

[0327] The preparation of other reference compound K49 differs in that benzylamine is used to substitute the acyl chloride position of intermediate II-2a.

[0328] Example 55: Synthesis of compound K46

[0329]

[0330] The preparation of other reference compound K49 differs in that aniline is used to substitute the acyl chloride position of intermediate II-2a.

[0331] Example 56: Synthesis of compound K47

[0332]

[0333] The preparation of other reference compound K49 differs in that ethylamine is used to substitute the acyl chloride position of intermediate II-2a.

[0334] Example 57: Synthesis of compound K48

[0335]

[0336] The preparation of other reference compound K49 differs in that 4-fluorobenzylamine is used to substitute the acyl chloride position of intermediate II-2a.

[0337] Example 58: Synthesis of compound K28

[0338]

[0339] Benzyl alcohol (2 mmol) was dissolved in DCM at low temperature (0-5℃), and triethylamine (3 mmol) was added. After stirring for 15 min, intermediate II-2a (2.4 mmol) solution dissolved in DCM was slowly added dropwise to the reaction system. After the reaction was completed by TLC monitoring, saturated sodium bicarbonate (50 ml) solution was added to the reaction system, and the mixture was extracted three times with ethyl acetate (15 ml). The organic layers were combined, and the organic phase was washed three times with saturated brine (100 ml). After drying and concentration, the mixture was subjected to column chromatography to obtain compound II-3c (a light yellow oily liquid).

[0340] Intermediate II-3c (1 mmol) was dissolved in DMF (10 ml), followed by the addition of Cs₂CO₃ (1.5 mmol). The reaction was monitored by TLC until completion. The reaction was terminated by adding water to the reaction system, and the mixture was extracted three times with ethyl acetate (15 ml). The organic layers were combined, washed three times with saturated brine (100 ml), dried, concentrated, and subjected to column chromatography to obtain compound K28 (a pale yellow solid).

[0341] Example 59: Synthesis of compound K29

[0342]

[0343] The preparation of other reference compound K28 differs in that tert-butyl alcohol is used to substitute the acyl chloride position of intermediate II-2a.

[0344] Example 60: Synthesis of compound K30

[0345]

[0346] The preparation of other reference compound K28 differs in that phenylpropanol is used to substitute the acyl chloride position of intermediate II-2a.

[0347] Example 61: Synthesis of compound K31

[0348]

[0349] The preparation of other reference compound K28 differs in that 2-difluoro-1-ol is used to substitute the acyl chloride position of intermediate II-2a.

[0350] Example 62: Synthesis of compound K32

[0351]

[0352] The preparation of other reference compound K28 differs in that 2-trifluoro-1-ol is used to substitute the acyl chloride position of intermediate II-2a.

[0353] Example 63: Synthesis of compound K33

[0354]

[0355] Intermediate II-1a (2 mmol) was dissolved in DCM at room temperature, p-methylphenylhydrazine (2 mmol) was added, and the mixture was stirred for 5 min. Triethylamine (3 mmol) was then added, and the mixture was stirred for another 15 min. HATU (3 mmol) was added, and the mixture was stirred at room temperature for 2 h. The reaction was monitored by TLC until completion. After removing the solvent, saturated sodium bicarbonate (50 ml) solution was added, and the mixture was extracted three times with ethyl acetate (15 ml). The extracts were washed with saturated brine (100 ml), and the organic layers were combined, dried, concentrated, and subjected to column chromatography to obtain compound II-3d (yellow solid).

[0356] Intermediate II-3d (1 mmol) was dissolved in DMF (10 ml), followed by the addition of Cs₂CO₃ (1.5 mmol). The reaction was monitored by TLC until completion. The reaction was terminated by adding water to the reaction system, and the mixture was extracted three times with ethyl acetate (15 ml). The organic layers were combined, washed three times with saturated brine (100 ml), dried, concentrated, and subjected to column chromatography to obtain compound K33 (yellow solid).

[0357] Example 64: Synthesis of compound K34

[0358]

[0359] The preparation of other reference compound K33 differs in that it involves the condensation of p-fluorophenylhydrazine with the carboxyl group of intermediate II-1a.

[0360] Example 65: Synthesis of compound K35

[0361]

[0362] Benzenesulfonic anhydride (3 mmol) was dissolved in DCM at low temperature (0-5℃), and DMAP (2 mmol) was added. After stirring for 5 min, intermediate II-2a (2 mmol) dissolved in DCM was added dropwise. After the addition was complete, triethylamine (3 mmol) was added, and the mixture was stirred from low temperature to room temperature. The reaction was monitored by TLC until completion. The solvent was removed, and saturated sodium bicarbonate (50 ml) solution was added. The mixture was extracted three times with ethyl acetate (15 ml), washed with saturated brine (100 ml), and the organic layers were combined, dried, concentrated, and subjected to column chromatography to obtain compound II-3e (a pale yellow oily liquid).

[0363] Intermediate II-3e (1 mmol) was dissolved in DMF (10 ml), followed by the addition of Cs₂CO₃ (1.5 mmol). The reaction was monitored by TLC until completion. The reaction was terminated by adding water to the reaction system, and the mixture was extracted three times with ethyl acetate (15 ml). The organic layers were combined, washed three times with saturated brine (100 ml), dried, concentrated, and subjected to column chromatography to obtain compound K35 (yellow solid).

[0364] Example 66: Synthesis of compound K36

[0365]

[0366] The preparation of other reference compound K35 differs in that p-toluenesulfonic anhydride is used to substitute the acyl chloride position of intermediate II-2a.

[0367] Example 67: Synthesis of compound K37

[0368]

[0369] The preparation of other reference compound K35 differs in that p-fluorobenzenesulfonic anhydride is used to substitute the acyl chloride position of intermediate II-2a.

[0370] Example 68: Synthesis of compound K38

[0371]

[0372] Benzenesulfonamide (3 mmol) was dissolved in DCM at low temperature (0-5℃), and HATU (2 mmol) was added. After stirring for 5 min, intermediate II-2a (2 mmol) dissolved in DCM was added dropwise. After the addition was complete, triethylamine (3 mmol) was added, and the mixture was stirred from low temperature to room temperature. The reaction was monitored by TLC until completion. The solvent was removed, and saturated sodium bicarbonate (50 ml) solution was added. The mixture was extracted three times with ethyl acetate (15 ml), washed with saturated brine (100 ml), and the organic layers were combined, dried, concentrated, and subjected to column chromatography to obtain compound II-3f (a pale yellow solid).

[0373] Intermediate II-3f (1 mmol) was dissolved in DMF (10 ml), followed by the addition of Cs₂CO₃ (1.5 mmol). The reaction was monitored by TLC until completion. The reaction was terminated by adding water to the reaction system, and the mixture was extracted three times with ethyl acetate (15 ml). The organic layers were combined, washed three times with saturated brine (100 ml), dried, concentrated, and subjected to column chromatography to obtain compound K38 (yellow solid).

[0374] Example 69: Synthesis of compound K39

[0375]

[0376] The preparation of other reference compound K38 differs in that p-toluenesulfonamide is used to substitute the acyl chloride position of intermediate II-2a.

[0377] Example 70: Synthesis of compound K40

[0378]

[0379] The preparation of other reference compound K38 differs in that p-fluorobenzenesulfonamide is used to substitute the acyl chloride position of intermediate II-2a.

[0380] Example 71: Synthesis of compound K50

[0381]

[0382] Compound K1 (1 mmol) was dissolved in tetrahydrofuran (15 ml), and K2CO3 (4 mmol) was added under ice bath conditions. After the reaction system stabilized, iodomethane (2 mmol) was added, and the mixture was stirred at room temperature until the reaction was complete as monitored by TLC. Tetrahydrofuran was removed by vacuum distillation, and the mixture was extracted three times with ethyl acetate (15 ml). The organic layers were combined, washed three times with saturated sodium chloride solution (100 ml), dried, concentrated, and then subjected to column chromatography to extract compound K50 (yellow solid).

[0383] Example 72: Synthesis of compound K51

[0384]

[0385] The preparation of other reference compound K50 differs in that bromoethane is used to substitute the hydroxyl position of compound K1.

[0386] Example 73: Synthesis of compound K52

[0387]

[0388] The preparation of other reference compound K50 differs in that bromoethane is used to substitute the hydroxyl position of compound K1.

[0389] Example 74: Synthesis of compound K53

[0390]

[0391] The preparation of other reference compound K50 differs in that 4-bromo-2-methyl-dibutene is used to substitute the hydroxyl position of compound K1.

[0392] Example 75: Synthesis of compound K54

[0393]

[0394] The preparation of other reference compound K50 differs in that 2,4-dimethylbenzyl bromide is used to substitute the hydroxyl position of compound K1.

[0395] Example 76: Synthesis of compound K55

[0396]

[0397] The preparation of other reference compound K50 differs in that 2,4-difluorobenzyl bromide is used to substitute the hydroxyl position of compound K1.

[0398] Example 77: Synthesis of compound K56

[0399]

[0400] The preparation of other reference compound K50 differs in that 4-trifluoromethylbenzyl bromide is used to substitute the hydroxyl position of compound K1.

[0401] Example 78: Synthesis of compound K57

[0402]

[0403] The preparation of other reference compounds K50 differs in that 2-cyanobenzyl bromide is used to substitute the hydroxyl position of compound K1.

[0404] Example 79: Synthesis of compound K58

[0405]

[0406] The preparation of other reference compounds K50 differs in that bromomethylcyclohexane is used to substitute the hydroxyl position of compound K1.

[0407] Example 80: Synthesis of compound K59

[0408]

[0409] The preparation of other reference compound K50 differs in that 3-bromopropene is used to substitute the hydroxyl position of compound K1.

[0410] Example 81: Synthesis of compound K60

[0411]

[0412] The preparation of other reference compounds K50 differs in that 4-fluorobenzyl bromide is used to substitute the hydroxyl position of compound K1.

[0413] Example 82: Synthesis of compound K61

[0414]

[0415] The preparation of other reference compound K50 differs in that 3,5-dimethoxybenzyl bromide is used to substitute the hydroxyl position of compound K1.

[0416] Example 83: Synthesis of compound K62

[0417]

[0418] The preparation of other reference compounds K50 differs in that iodopropane is used to substitute the hydroxyl position of compound K1.

[0419] Example 84: Synthesis of compound K63

[0420]

[0421] The preparation of other reference compound K50 differs in that 2-trifluoromethylbenzyl bromide is used to substitute the hydroxyl position of compound K1.

[0422] Example 85: Synthesis of compound K64

[0423]

[0424] The preparation of other reference compound K50 differs in that 2,4-difluorobenzyl bromide is used to substitute the hydroxyl position of compound K1.

[0425] Example 86: Synthesis of compound K65

[0426]

[0427] The preparation of other reference compound K50 differs in that 2-bromobenzyl bromide is used to substitute the hydroxyl position of compound K1.

[0428] Example 87: Synthesis of compound K66

[0429]

[0430] The preparation of other reference compound K50 differs in that 2-fluorobenzyl bromide is used to substitute the hydroxyl position of compound K1.

[0431] Example 88: Synthesis of compound K67

[0432]

[0433] The preparation of other reference compound K50 differs in that 2-chlorobenzyl bromide is used to substitute the hydroxyl position of compound K1.

[0434] Example 89: Synthesis of compound K68

[0435]

[0436] The preparation of other reference compound K50 differs in that 4-isopropylbenzyl bromide is used to substitute the hydroxyl position of compound K1.

[0437] Example 90: Synthesis of compound K69

[0438]

[0439] The preparation of other reference compound K50 differs in that 3,4,5-trifluorobenzyl bromide is used to substitute the hydroxyl position of compound K1.

[0440] Example 91: Synthesis of compound K70

[0441]

[0442] The preparation of other reference compound K50 differs in that bromomethylcyclopentane is used to substitute the hydroxyl position of compound K1.

[0443] Example 92: Synthesis of compound K71

[0444]

[0445] The preparation of other reference compound K50 differs in that 4-nitrobenzyl bromide is used to substitute the hydroxyl position of compound K1.

[0446] Example 93: Synthesis of compound K72

[0447]

[0448] The preparation of other reference compound K50 differs in that 1-bromomethylnaphthalene is used to substitute the hydroxyl position of compound K1.

[0449] Example 94: Synthesis of compound K86

[0450]

[0451] At -78°C, intermediate I-3a (2 mmol) was dissolved in THF, and LDA (2.2 mmol) was added. After stirring for 15 min, ethyl acetate (3 mmol) was added. After 0.5 h, the reaction system was transferred to room temperature and the reaction was continued for another 0.5 h. The reaction was monitored by TLC until completion. The reaction system was quenched in 1 M ammonium chloride aqueous solution (50 ml), extracted three times with ethyl acetate (15 mmol), washed with saturated brine (100 ml), and the organic layers were combined, dried, concentrated, and subjected to column chromatography to obtain compound II-3f (a pale yellow solid).

[0452] Intermediate III-a (1 mmol) was dissolved in DMF (10 ml), followed by the addition of Cs₂CO₃ (1.5 mmol). The reaction was monitored by TLC until completion. The reaction was terminated by adding water to the reaction system, and the mixture was extracted three times with ethyl acetate (15 ml). The organic layers were combined, washed three times with saturated brine (100 ml), dried, concentrated, and subjected to column chromatography to obtain compound K86 (yellow solid).

[0453] Example 95: Synthesis of compound K87

[0454]

[0455] The preparation of other reference compound K86 differs in that ethyl propionate is used to substitute the carbonyl α-position of compound I-3a.

[0456] Example 96: Synthesis of compound K88

[0457]

[0458] The preparation of other reference compound K50 differs in that ethyl benzoate is used to substitute the carbonyl α-position of compound I-3a.

[0459] The α-hydroxy ester compounds of the present invention with indolocyclohexanone as the backbone were synthesized according to the above method. Table 1 below lists the structural characterization data of some compounds of the present invention.

[0460] Table 1 shows the physical properties and spectral characterization of specific compounds of Formula I.

[0461] ;

[0462] ;

[0463] ; ;

[0464] ;

[0465] ;

[0466] ;

[0467] ;

[0468] ;

[0469] Example 13: Herbicidal Activity Test (Greenhouse Pot Method)

[0470] The synthesized compounds underwent initial screening (pot method): the targets were foxtail grass, barnyard grass, eclipta prostrata, and amaranth retroflexus. 7cm inner diameter pots were filled with composite soil (vermiculite:seedling substrate = 1:2, v / v) to 3 / 4 full, and the four weed targets (germination rate ≥ 85%) were directly sown, covered with 0.2cm of soil, and left to grow until the weeds reached approximately the 3-leaf stage. Each compound was applied at a dosage of 500g ai / ha using an automatic sprayer. After the pesticide solution dried on the crop leaves, the plants were transferred to a greenhouse for cultivation (28℃-32℃, 70% humidity). The results were collected after 21 days. The results are shown in Table 2.

[0471] Investigation method: After 30 days of experimental treatment, the symptoms of damage and growth inhibition of the target were visually observed, and the fresh weight of the aboveground parts was measured. The fresh weight inhibition rate (%) was calculated and the control effect (%) was expressed by the fresh weight inhibition rate.

[0472] Fresh weight inhibition rate (%) = (Control fresh weight - Treatment fresh weight) / Control fresh weight × 100

[0473] Based on the fresh weight inhibition rate and visual observation of weed damage symptoms, weed suppression is divided into the following five levels:

[0474] Grade A is complete mortality: fresh weight inhibition rate is greater than 80% and less than or equal to 100%, and the weed leaves are withered and dead.

[0475] Grade B is basically dead: the fresh weight inhibition rate is greater than 60% and less than or equal to 80%, most of the weed leaves are dried out or the plants are deformed, with white leaf tips, and unable to grow normally.

[0476] Grade C is characterized by a small number of deaths: fresh weight inhibition rate greater than 40% and less than or equal to 60%, very few weed leaves reach the effect of drying out or the plant growth is slightly deformed and the leaf tips are whitened.

[0477] Grade D indicates a slight inhibitory effect, but without the death effect: the fresh weight inhibition rate is greater than 20% and less than or equal to 40%, the weed leaves do not reach the drying effect, and the plants show a slight inhibitory effect in height or thickness.

[0478] Grade E indicates virtually no inhibitory effect: the plants grow normally with no obvious inhibitory effect.

[0479] Table 2. Herbicidal activity inhibition rate (%) of compounds of formula I (dose 500g ai / ha)

[0480] ;

[0481] ;

[0482] Four weed species were used in the experiment: two dicotyledonous plants, *Eclipta prostrata* and *Amaranthus retroflexus*, and two monocotyledonous plants, *Barnyardgrass* and *Setaria viridis*. The positive controls were the commercially available ALS herbicides penflusulfonamide and bispyribac-sodium, while the blank control group received an appropriate volume of DMSO. The initial screening data showed that some compounds significantly inhibited weed growth, but their weeding effect was still somewhat lower than that of the positive controls penflusulfonamide and bispyribac-sodium. Overall, this series of compounds showed a more significant inhibitory effect on dicotyledonous weeds, especially on *Amaranthus retroflexus*. Compounds K1, K8, and K9 all achieved fresh weight inhibition rates of over 80% against *Amaranthus retroflexus*, while compounds K3, K4, K11, and K14 also achieved fresh weight inhibition rates of over 70%. Furthermore, all seven compounds achieved fresh weight inhibition rates of over 70% against *Eclipta prostrata*. Among monocotyledonous weeds, this series of compounds did not show excellent herbicidal effects against barnyardgrass. Only K1 achieved a fresh weight inhibition rate of 65%, and a significant growth-inhibiting effect was observed phenotypically. The target compounds showed significantly stronger growth inhibition against foxtail millet than against barnyardgrass, with K1, K8, and K9 all achieving fresh weight inhibition rates of over 70% against foxtail millet. In terms of the inhibitory effects on these four weeds, the herbicidal activity of the target compounds is still somewhat inferior to that of penflusulfonate and bispyribac-sodium. However, compounds K1, K8, and K9 showed significant growth-inhibiting effects against amaranth, angelica sinensis, and foxtail millet, providing a clear direction for future optimization of this series of compounds.

Claims

1. A compound containing an α-hydroxy ester with an indolecyclohexanone backbone, characterized in that, It has the structure shown in Equation I. ； In Equation I, R 1 Selected from H, substituted or substituted C1-C 12 Alkyl, C2-C6 alkenyl, C2-C6 alkynyl, substituted or unsubstituted phenyl, benzyl, naphthyl, pyrrolithyl, furanyl, tetrahydrofuranyl, thiophenyl, thiazolyl, imidazolyl, pyrazolyl, oxazolyl, valproic acid, pyridyl, pyranyl, piperidinyl, piperazine, pyridazine, pyrimidinyl, caprolactamyl, C3-C8 heterocycle; R 2 Selected from any group from X1-X6 below; ； Among them, A in X1-X6 1 A 2 A 3a A 3b A 4 A 5 A 6a A 6b Each of the following is independently selected from H, C1-C8 alkyl, halogen-substituted C1-C8 alkyl, phenyl, benzyl, naphthyl, pyridyl, furanyl, thiophene, pyrazolyl, imidazolyl, phenyl, benzyl, naphthyl, pyridyl, furanyl, thiophene, pyrazolyl, imidazolyl, and C3-C8 heterocycles substituted with C1-C8 alkyl and / or halogens; R 3 Selected from H, substituted or unsubstituted C1-C 12 Alkyl, C2-C6 alkenyl, C2-C6 alkynyl, substituted or unsubstituted phenyl, benzyl, naphthyl, pyrrolithyl, furanyl, tetrahydrofuranyl, thiophenyl, thiazolyl, imidazolyl, pyrazolyl, oxazolyl, valproic acid, pyridyl, pyranyl, piperidinyl, piperazine, pyridazine, pyrimidinyl, caprolactamyl, C3-C8 heterocycle; R 4 Selected from H, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, substituted or unsubstituted phenyl, substituted or unsubstituted phenoxy, benzyl, substituted or unsubstituted benzyloxy, naphthyl, pyrroleyl, furanyl, tetrahydrofuranyl, thiopheneyl, thiazolyl, imidazolyl, pyrazolyl, oxazolyl, valeronyl, pyridyl, pyranyl, piperidinyl, piperazinyl, pyridazinyl, pyrimidinyl, caprolactamyl, C3-C8 heterocycle; and R 1 R 3 or R 4 When substituents are present, they are each independently selected from halogens, C1-C6 alkyl groups, C1-C6 alkoxy groups, C1-C6 alkyl groups substituted with halogens, C1-C6 alkoxy groups substituted with halogens, phenoxy groups, nitro groups, cyano groups, and amino groups. n=1，2，3，4，5，6。 2. The compound according to claim 1, characterized in that, In the compound, R 1 Selected from H, or CH2R 5 , where R 5 Selected from H, C1-C3 alkyl, C5-C6 cycloalkyl, C2-C5 alkenyl, C2-C5 alkynyl, halogen-substituted C1-C6 alkyl, or halogen-substituted C1-C3 alkyl, cyano, C1-C3 alkoxy, halogen-substituted C1-C6 alkoxy, nitro-substituted or unsubstituted phenyl, naphthyl; R 2 Any group selected from X1-X6, wherein, among X1-X6, A 1 A 2 A 3a A 3b A 4 A 5 A 6a A 6b Each of the following is independently selected from H, C1-C4 alkyl chains, C1-C4 alkyl chains substituted with one or more halogens, phenyl groups substituted with or unsubstituted with C1-C3 alkyl chains and / or amino groups and / or halogens, and benzyl groups; R 3 Selected from H, C1-C8 alkyl, C2-C4 alkenyl, C2-C6 alkynyl, and halogen-substituted C1-C 12 Alkyl, C1-C3 alkyl and / or halogen and / or cyano and / or C1-C3 alkoxy and / or halogen-substituted C1-C3 alkyl and / or amino-substituted or unsubstituted phenyl, benzyl, naphthyl; R 4 Selected from H, halogens, substituted or unsubstituted C1-C12 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, substituted or unsubstituted phenyl, benzyl, naphthyl, pyrrolithyl, furanyl, tetrahydrofuranyl, thiophenyl, thiazolyl, imidazolyl, pyrazolyl, oxazolyl, valproamide, pyridyl, pyranyl, piperidinyl, piperazinyl, pyridazinyl, pyrimidinyl, caprolactamyl, and C3-C8 heterocycles; n=1，2，3，4。 3. The compound according to claim 1, characterized in that, In the compound, R 1 Selected from -CH2-C6H5, -CH3, -CH2CH=C(CH3)2, -CH2-3,5-2F-C6H3, -CH2-4-CF3-C6H4, -CH2-2-C≡N-C6H4, -CH2-C6H 11 , -CH2CH=CH2, -CH2-3,5-2OCH3-C6H3, -CH2CH2CH3, -CH2-2-CF3-C6H4, -CH2-2,6-2F-C6H3, -CH2-2-F-3-CF2OCH3-C6H3, -CH2-2 -Br-C6H4, -CH2-2-F-C6H4, -CH2-2-Cl-C6H4, -CH2-2,6-2Cl-C6H3, -CH2-3,4,5-3F-C6H2, -CH2-C5H9, -CH2-4-NO2-C6H4, -CH2-C 10 Any one of H7; R 2 Selected from -COOCH3, -COOC(CH3)3, -COOCH2C6H5, -COO(CH2)3C6H5, -COOCH2CHF2, -COOCH2CF3, -COONHNH -4-CH3-C6H5, -COONHNH-4-F-C6H5, -COOSO2C6H5, -COOSO2-4-CH3-C6H5, -COOSO2-4-F-C6H5, -CO Any one of NHSO2-4-CH3-C6H5, -CONHSO2-4-F-C6H5, -CONC3H6, -CON-3-OCH3-C3H5, -CON-3-F-C3H5, -CONC4H8, -CONHCH2C6H5, -CONHC6H5, -CONHCH2CH3, -CONHCH2-4-F-C6H4, -CONHCH2-4-CH3-C6H4; R 3 selected from -H, -CH3, -CH2CH3, -CH2CH2CH 3、 -CH2-C6H5, -CH2CH=C(CH3)2, -CH2-3,5-diCH3-C6H3, -CH2-3,5-diF-C6H3, -CH2-4-CF3-C6H4, -CH2-2-C≡N-C6H4, -CH2-C6H 11 , -CH2CH=CH2, -CH2-4-F-C6H4, -CH2-3,5-diOCH3-C6H3, -CH2-2-CF3-C6H4, -CH2-2,6-diF-C6H3, -CH2-2-Br-C6H4, -CH2-2-F-C6H4, -CH2-2-Cl-C6H4, -CH2-4-CH(CH3)2-C6H4, -CH2-3,4,5-triF-C6H2, -CH2-C5H9, -CH2-4-NO2-C6H4, -CH2-C 10 H7; R 4 Selected from -H, -F, -Cl, -Br, -I, -CH2-C6H5, -CH3, -CH2CH=C(CH3)2, -CH2-3,5-2F-C6H3, -CH2-4-CF3-C6H4, -CH2-2-C≡N-C6H4, -CH2-C6H 11 , -CH2CH=CH2, -CH2-3,5-2OCH3-C6H3, -CH2CH2CH3, -CH2-2-CF3-C6H4, -CH2-2,6-2F-C6H3, -CH2-2-F-3-CF2OCH3-C6H3, -CH2-2 -Br-C6H4, -CH2-2-F-C6H4, -CH2-2-Cl-C6H4, -CH2-2,6-2Cl-C6H3, -CH2-3,4,5-3F-C6H2, -CH2-C5H9, -CH2-4-NO2-C6H4, -CH2-C 10 H7, -OCH3, -OCH2C6H5, -OCH2-3,5-2F-C6H3, -OCH2-4-CF3-C6H4, -OCH2-2-C≡N-C6H4, -OCH2-C6H 11 , -OCH2CH=CH2, -OCH2-3,5-2OCH3-C6H3, -OCH2CH2CH3, -OCH2-2-CF3-C6H4, -OCH2-2,6-2F-C6H3, -OCH2-2-F-3-CF2OCH3-C6H3, -OCH2-2 -Br-C6H4, -OCH2-2-F-C6H4, -OCH2-2-Cl-C6H4, -OCH2-2,6-2Cl-C6H3, -OCH2-3,4,5-3F-C6H2, -OCH2-C5H9, -OCH2-4-NO2-C6H4, -OCH2-C 10 Any of the H7 types.

4. The compound according to claim 3, characterized in that, The compound is selected from any one of the following: Compound K1: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K2: R 1 -CH2-3,5-2CH3-C6H3, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K3: R 1 For -CH2-2-Cl-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K4: R 1 -CH2-2,6-2F-C6H3, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K5: R 1 For -CH2-2-I-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K6: R 1 For -CH2-2-Br-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K7: R 1 The value is -CH2-2,6-2Cl-C6H3, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K8: R 1 For -CH2CH3, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K9: R 1 For -CH3, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K10: R 1 -CH2-3,5-2OCH3-C6H3, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K11: R 1 For -CH2CH2CH3, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K12: R 1 For -CH2-3-Cl-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K13: R 1 It is -CH2-4-F-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K14: R 1 -CH2-3,5-2F-4-OCH3-C6H3, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K15: R 1 For -CH2-C6H5, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K16: R 1 For -CH2CH=CH2, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K17: R 1 For -CH2CH=C(CH3)2, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K18: R 1 -CH2-3,5-2F-C6H3, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K19: R 1 For -CH2-4-CF3-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K20:R 1 For -CH2-2-C≡N-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K21: R 1 -CH2-C6H 11 R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K22: R 1 For -CH2-2-CF3-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K23: R 1 The value is -CH2-4-CH(CH3)2-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K24: R 1 -CH2-3,4,5-3F-C6H2, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K25: R 1 For -CH2-C5H9, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K26: R 1 For -CH2-4-NO2-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K27: R 1 -CH2-C 10 H7, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K28: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH2C6H5, R 3 -H, R 4 -H; Compound K29: R 1 For -CH2-2-F-C6H4, R 2 For -COOC(CH3)3, R 3 -H, R 4 -H; Compound K30: R 1 For -CH2-2-F-C6H4, R 2 -COO(CH2)3C6H5, R 3 -H, R 4 -H; Compound K31: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH2CHF2, R 3 -H, R 4 -H; Compound K32: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH2CF3, R 3 -H, R 4 -H; Compound K33: R 1 For -CH2-2-F-C6H4, R 2 -COONHNH-4-CH3-C6H5, R 3 -H, R 4 -H; Compound K34: R 1 For -CH2-2-F-C6H4, R 2 For -COONHNH-4-F-C6H5, R 3 -H, R 4 -H; Compound K35: R 1 For -CH2-2-F-C6H4, R 2 For -COOSO2C6H5, R 3 -H, R 4 -H; Compound K36: R 1 For -CH2-2-F-C6H4, R 2 For -COOSO2-4-CH3-C6H5, R 3 -H, R 4 -H; Compound K37: R 1 For -CH2-2-F-C6H4, R 2 For -COOSO2-4-F-C6H5, R 3 -H, R 4 -H; Compound K38: R 1 For -CH2-2-F-C6H4, R 2 For -CONHSO2C6H5, R 3 -H, R 4 -H; Compound K39: R 1 For -CH2-2-F-C6H4, R 2 For -CONHSO2-4-CH3-C6H5, R 3 -H, R 4 -H; Compound K40: R 1 For -CH2-2-F-C6H4, R 2 For -CONHSO2-4-F-C6H5, R 3 -H, R 4 -H; Compound K41: R 1 For -CH2-2-F-C6H4, R 2 For -CONC3H6, R 3 -H, R 4 -H; Compound K42: R 1 For -CH2-2-F-C6H4, R 2 For -CON-3-OCH3-C3H5, R 3 -H, R 4 -H; Compound K43: R 1 For -CH2-2-F-C6H4, R 2 For -CON-3-F-C3H5, R 3 -H, R 4 -H; Compound K44: R 1 For -CH2-2-F-C6H4, R 2 For -CONC4H8, R 3 -H, R 4 -H; Compound K45: R 1 For -CH2-2-F-C6H4, R 2 For -CONHCH2C6H5, R 3 -H, R 4 -H; Compound K46: R 1 For -CH2-2-F-C6H4, R 2 For -CONHC6H5, R 3 -H, R 4 -H; Compound K47: R 1 For -CH2-2-F-C6H4, R 2 For -CONHCH2CH3, R 3 -H, R 4 -H; Compound K48: R 1 For -CH2-2-F-C6H4, R 2 For -CONHCH2-4-F-C6H4, R 3 -H, R 4 -H; Compound K49: R 1 For -CH2-2-F-C6H4, R 2 For -CONHCH2-4-CH3-C6H4, R 3 -H, R 4 -H; Compound K50: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH3, R 4 -H; Compound K51: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2CH3, R 4 -H; Compound K52: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2-C6H5, R 4 -H; Compound K53: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2CH=C(CH3)2, R 4 -H; Compound K54: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 -CH2-3,5-2CH3-C6H3, R 4 -H; Compound K55: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 -CH2-3,5-2F-C6H3, R 4 -H; Compound K56: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2-4-CF3-C6H4, R 4 -H; Compound K57: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2-2-C≡N-C6H4, R 4 -H; Compound K58: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 -CH2-C6H 11 R 4 -H; Compound K59: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2CH=CH2, R 4 -H; Compound K60: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 It is -CH2-4-F-C6H4, R 4 -H; Compound K61: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 -CH2-3,5-2OCH3-C6H3, R 4 -H; Compound K62: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2CH2CH3, R 4 -H; Compound K63: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2-2-CF3-C6H4, R 4 -H; Compound K64: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 -CH2-2,6-2F-C6H3, R 4 -H; Compound K65: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2-2-Br-C6H4, R 4 -H; Compound K66: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2-2-F-C6H4, R 4 -H; Compound K67: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2-2-Cl-C6H4, R 4 -H; Compound K68: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 The value is -CH2-4-CH(CH3)2-C6H4, R 4 -H; Compound K69: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 -CH2-3,4,5-3F-C6H2, R 4 -H; Compound K70: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2-C5H9, R 4 -H; Compound K71: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 For -CH2-4-NO2-C6H4, R 4 -H; Compound K72: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 -CH2-C 10 H7, R 4 -H; Compound K73: R 1 -CH2-2,4-2F-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K74: R 1 -CH(CH3)2, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K75: R 1 For -CH2-4-OCH3-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K76: R 1 For -CH2-3-F-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K77: R 1 For -CH2-2-CH3-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K78: R 1 For -CH2-3-OCH3-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K79: R 1 For -CH2-C4H7, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K80: R 1 For -CH2OCH3, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K81: R 1 For -CH2-C3H5, R 2 For -COOCH3, R 3 -H, R 4 -H; Compound K82: R 1 For -CH3, R 2 For -COOCH3, R 3 -H, R 4 -6-F; Compound K83: R 1 For -CH2CH3, R 2 For -COOCH3, R 3 -H, R 4 -6-F; Compound K84: R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 -H, R 4 -6-F; Compound K85: R 1 For -COCH3, R 2 For -COOCH3, R 3 -H, R 4 -6-F; Compound K86: R 1 For -CH2-2-F-C6H4, R 2 For -COCH3, R 3 -H, R 4 -H; Compound K87: R 1 For -CH2-2-F-C6H4, R 2 For -COCH2CH3, R 3 -H, R 4 -H; Compound K88: R 1 For -CH2-2-F-C6H4, R 2 For -COC6H4, R 3 -H, R 4 -H; Compound K89: R 1 For -CH3, R 2 For -COOCH3, R 3 -H, R 4 -7-F; Compound K90: R 1 For -CH3, R 2 For -COOCH3, R 3 -H, R 4 It is -6-CH3; Compound K91:R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 -H, R 4 It is -6-CH3; Compound K92: R 1 For -CH2CH3, R 2 For -COOCH3, R 3 -H, R 4 It is -6-OCH3; Compound K93: R 1 For -CH3, R 2 For -COOCH3, R 3 -H, R 4 It is -6-OCH3; Compound K94:R 1 For -CH2-2-F-C6H4, R 2 For -COOCH3, R 3 -H, R 4 It is -6-OCH3.

5. The method for preparing the compound according to any one of claims 1-4, characterized in that, The synthetic route for the compound is selected from any one of the following F1-F3: F1： ； F2： ； F3： 。 6. The preparation method according to claim 5, characterized in that, In step A, the synthesis method of formula I-2 is as follows: substituted phenylhydrazine hydrochloride is added to a container containing anhydrous acetic acid, and the mixture is heated to reflux and stirred; initial raw material I-1 is slowly added dropwise to the reaction system. After the addition is complete, the reaction system is stirred under reflux conditions. After the reaction is complete, water is added to quench the reaction system. After the reaction system cools to room temperature, the reaction system is poured into ice water, ethyl acetate is added for extraction, and the organic phase is washed 2-4 times with saturated brine. The organic layers are combined, and the organic phase is dried, concentrated, and subjected to column chromatography to obtain intermediate compound I-2. In step B, the synthesis method of formula I-3 is as follows: intermediate I-2 is dissolved in anhydrous tetrahydrofuran, NaH is added under ice bath conditions, and after the reaction system is stable, the halogenated product is added and the mixture is stirred at room temperature until the reaction is complete; ice water is added to the reaction system to quench NaH, tetrahydrofuran is removed by vacuum distillation, ethyl acetate is added for extraction 2-4 times, the organic layers are combined, the organic phase is washed three times with saturated sodium chloride solution, dried and concentrated, and column chromatography is performed to obtain intermediate I-3 of a series of compounds; In step C, the synthesis method of formula I-4 is as follows: intermediate I-3 of the series of compounds is dissolved in anhydrous tetrahydrofuran. Under ice bath conditions, it is slowly added to a Schlenk flask containing NaH. The entire reaction system is carried out under nitrogen protection. After the reaction system is stable, the temperature of the reaction system is increased to 70°C. DMC is slowly added to the reaction system, and the mixture is stirred at 70°C until the reaction is complete. Ice water is added to the reaction system to quench NaH. Tetrahydrofuran is removed by vacuum distillation. Ethyl acetate is added for extraction 2-4 times. The organic layers are combined. The organic phase is washed three times with saturated sodium chloride solution. After drying and concentration, column chromatography is performed to obtain intermediate I-4 of the series of compounds. In step D, the synthesis method of formula I-5 is as follows: intermediate II-4 of the series of compounds is dissolved in DMF, then Cs2CO3 is added until the reaction is completed, water is added to the reaction system to terminate the reaction, ethyl acetate is extracted 2-4 times, the organic layers are combined, the organic phase is washed 2-4 times with saturated brine, dried and concentrated, and then column chromatography is performed to obtain the series of target compounds I-5. In step E, the synthesis method of formula II-1 is as follows: dissolve the intermediate of formula I-4 in a solvent, add sodium hydroxide solution dropwise, stir at room temperature, and after the reaction is complete, remove the organic solvent, acidify with 2N hydrochloric acid to pH=1.5-2.5, precipitate the solid, filter and dry to obtain intermediate of formula II-1; In step F, the synthesis method of formula II-2 is as follows: dissolve raw material II-1 in a solvent, add oxaloyl chloride dropwise, stir the reaction at -5℃ to 5℃, and after the reaction is completed, remove the solvent and the remaining solid is the intermediate of formula II-2; In step G, the synthesis method of formula II-3 is as follows: at 0-5℃, an alcoholic raw material, an amine raw material, a sulfonic acid, a sulfonamide, or a cyclic amine intermediate is dissolved in a solvent, and triethylamine is added. After stirring, the solution of intermediate II-2 dissolved in the solvent is added dropwise to the above reaction system. After the reaction is completed, a saturated sodium bicarbonate solution is added to the reaction system, the organic layers are extracted and combined, dried and concentrated, and column chromatography is performed to obtain intermediate II-3. In step H, the synthesis method of formula II-4 is as follows: intermediate II-3 and Cs2CO3 are dissolved in a solvent, stirred at room temperature under aerobic conditions, and after the reaction is completed, the mixture is extracted, washed with saturated brine, the organic layers are combined, dried and concentrated by column chromatography to obtain formula II-4. In step I, the synthesis method of formula III is as follows: dissolve formula I-5 and K2CO3 in a solvent, add the halogenated product, stir at room temperature, and after the reaction is complete, extract, wash with saturated brine, combine the organic layers, dry and concentrate column chromatography to obtain formula III; The solvent in step AJ is selected from any one of water, N,N-dimethylformamide, acetonitrile, N,N-diethylacetamide, dichloromethane, 1,4-dioxane, toluene, dimethyl sulfoxide, tetrahydrofuran, acetic acid, methanol, and ethanol.

7. The use of the compound according to any one of claims 1-4 in the preparation of pesticide herbicides.

8. The application according to claim 7, characterized in that, The herbicide controls at least one of the following weeds: grasses, broadleaf weeds, and sedges.

9. The application according to claim 8, characterized in that, The broadleaf weeds mentioned are any one of the following: amaranth, lamb's quarters, velvetleaf, rice-wrapping grass, cassia seed, morning glory, cocklebur, reverse-branch amaranth, false groundcherry, angelica sinensis, purslane, spiny amaranth, water bamboo leaf, wild arrowhead, water plantain, rain-dew flower, dayflower, and duck tongue grass; The sedges are selected from at least one of Cyperus rotundus and Cyperus heterophylla; The grassy weeds mentioned are at least one of the following: foxtail grass, barnyard grass, barnyard grass, crabgrass, jointed barley, wild oat, wild oat, and Japanese wild oat.

10. A pesticide herbicide, wherein the active ingredient of the pesticide herbicide comprises at least one of the compounds described in any one of claims 1-4; The herbicide is composed of active ingredients and excipients, and the content of the active ingredients is 1 to 99.9999 by weight.

11. The pesticide herbicide according to claim 10, wherein, The content of the active ingredient is 1-50% by weight; the formulation of the pesticide herbicide is selected from any one of emulsifiable concentrate, suspension concentrate, wettable powder, powder, granule, aqueous solution, poison bait, mother liquor or mother powder.

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