Heterocyclic-substituted aromatic compounds, methods for their preparation, herbicidal compositions and uses

Abstract

The present application belongs to the technical field of pesticides, and particularly relates to a heterocyclic-substituted aromatic compound, a preparation method thereof, a herbicidal composition and application. The compound is shown in general formula I: wherein Y represents halogen, halogenated alkyl, cyano, nitro or amino; Z represents hydrogen, halogen or hydroxyl; M1 and M2 independently represent CR5 or N(O) m ; Q represents CX3X4; R1, R2, R3, R4 and R5 independently represent hydrogen, halogen, etc.; X1, X2, X3 and X4 independently represent hydrogen, halogen, etc., and m represents 0 or 1. The compound has excellent herbicidal activity on gramineous weeds, broadleaf weeds and the like, and high selectivity on crops even at a low application rate.

Description

Technical Field

[0001] This invention belongs to the field of pesticide technology, specifically relating to a heterocyclic substituted aromatic compound, its preparation method, herbicidal composition, and application. Background Technology

[0002] Weed control is a crucial aspect of achieving efficient agriculture. Although a variety of herbicides are available on the market, such as the use of substituted biarylbenzenesulfonamide compounds as herbicides disclosed in patent WO2012059050A, the weeding performance and crop selectivity of these known compounds are not entirely satisfactory. Furthermore, due to the expanding market, weed resistance, herbicide lifespan, economic considerations, and increasing environmental awareness, scientists need to continuously research and develop new, efficient, safe, economical herbicides with different modes of action. Summary of the Invention

[0003] This invention provides a heterocyclic substituted aromatic compound, its preparation method, herbicidal composition, and application. The compound exhibits excellent herbicidal activity against grass weeds and broadleaf weeds even at low application rates, and is highly selective for crops.

[0004] The technical solution adopted in this invention is as follows:

[0005] A heterocyclic substituted aromatic compound, as shown in general formula I:

[0006]

[0007] in,

[0008] Y represents halogen, haloalkyl, cyano, nitro, or amino;

[0009] Z represents hydrogen, halogen, or hydroxyl;

[0010] M1 and M2 independently represent CR5 or N(O), respectively. m ;

[0011] Q represents CX3X4;

[0012] R1, R2, R3, R4, and R5 independently represent hydrogen, halogen, hydroxyl, mercapto, formyl, hydroxyalkyl, nitro, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, and -OR, respectively. 11 -SR 11 -(SO)R 11 -(SO2)R 11 -(SO2)OR 11 -O(SO2)R11 -N(R) 12 2. Phenyl or benzyl, wherein,

[0013] The "alkyl", "alkenyl", "alkynyl", "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl" or "cycloalkenylalkyl" are each independently unsubstituted or substituted with a halogen, and the "phenyl" or "benzyl" are each independently unsubstituted or substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy;

[0014] X1, X2, X3, and X4 independently represent hydrogen, halogen, nitro, cyano, cyanothio, hydroxyl, mercapto, sulfonic acid, formyl, haloformyl, azide, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, -PO(OR')2, -OR”, -(CO)R”, -SR”, -(SO)R”, -(SO2)R”, -Si(R”)3, -O(CO)R”, -O-(SO2)R”, -S(CO)R”, -(SO2)OR”, -O(CO)OR”, and -(CO)(CO)OR”. -CR'=N-OH, -CR'=NOR", heterocyclic group, heterocyclic alkyl group, aryl group, arylalkyl group, amino group, aminoalkyl group, aminocarbonylalkyl group, aminocarbonyloxyalkyl group, aminothiocarbonyloxyalkyl group, aminosulfonyl group or aminosulfonyloxyalkyl group, wherein,

[0015] The "alkyl", "alkenyl", or "alkynyl" groups are independently unsubstituted or substituted by at least one group selected from halogen, cyano, hydroxyl, mercapto, carboxyl, -OR", -(CO)R", -SR", -(SO2)R", -O(CO)H, -O(CO)R", -O-(SO2)R", -(CO)OR", -O(CO)OR", -O(CO)(CO)OH, -O(CO)(CO)OR", -O-alkyl-(CO)OH, or -O-alkyl-(CO)OR.

[0016] The terms "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclic", "heterocyclic alkyl", "aryl", or "arylalkyl" are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14)2 or -O-alkyl-(CO)OR 14 The ring is substituted by at least one group, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0017] The "amino", "aminoalkyl", "aminocarbonylalkyl", "aminocarbonyloxyalkyl", "aminothiocarbonyloxyalkyl", "aminosulfonyl" or "aminosulfonyloxyalkyl" are each independently unsubstituted or selected from -R 11 -OR 11 -(CO)R 11 -(CO)OR 11 ,-alkyl-(CO)OR 11 -(SO2)R 11 -(SO2)OR 11 ,-alkyl-(SO2)R 11 -(CO)N(R) 12 )2 or -(SO2)N(R 12 Substituted by one or two groups of )2;

[0018] R' independently represents hydrogen, halogen, alkoxy, alkoxyalkyl, alkyl, alkenyl, ynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclic or heterocyclic alkyl, wherein the "alkyl", "alkenyl" or "ynyl" is independently unsubstituted or halogen-substituted, and the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "aryl", "arylalkyl", "heterocyclic" or "heterocyclic alkyl" is independently unsubstituted or selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-alkyl-(CO)OR 14 The ring is substituted by at least one group, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0019] "R" independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, arylalkenyl, heterocyclic, heterocyclic alkyl, or heterocyclic alkenyl, wherein the "alkyl", "alkenyl", or "alkynyl" is independently unsubstituted or selected from halogen, cyano, trialkylsilyl, -OR 13 -SR 13 -O(CO)R 13 -(CO)R 13 -(CO)OR 13 OR-O(CO)OR 13 The group substituted by at least one of the following groups, wherein the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "aryl", "arylalkyl", "arylalkenyl", "heterocyclic", "heterocyclic alkyl" or "heterocyclic alkenyl" is independently unsubstituted or selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-alkyl-(CO)OR 14 The ring is substituted by at least one group, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0020] W1 represents O, S, or NW4;

[0021] W2 represents OW3, SW3, or NW4W5;

[0022] W3 independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclic, aryl, and so on. , , , or Wherein, the "alkyl", "alkenyl" or "alkynyl" is independently unsubstituted or selected from halogen, cyano, nitro, cycloalkyl, trialkylsilyl, cycloalkenyl, heterocyclic, aryl, , , , , , , , or The "cycloalkyl", "cycloalkenyl", "heterocyclic" or "aryl" group is substituted by at least one group, wherein the "cycloalkyl", "cycloalkenyl", "heterocyclic" or "aryl" group is independently unsubstituted or selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-alkyl-(CO)OR 14 The ring is substituted by at least one group, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0023] W4 and W5 independently represent hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclic, and aryl, respectively. , , , , , , , or Wherein, the "alkyl", "alkenyl" or "alkynyl" is independently unsubstituted or selected from halogen, cyano, nitro, cycloalkyl, trialkylsilyl, cycloalkenyl, heterocyclic, aryl, , , , , , , , or The "cycloalkyl", "cycloalkenyl", "heterocyclic" or "aryl" group is substituted by at least one group, wherein the "cycloalkyl", "cycloalkenyl", "heterocyclic" or "aryl" group is independently unsubstituted or selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-alkyl-(CO)OR 14 The ring is substituted by at least one group, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0024] Or NW4W5 represents Or an unsubstituted or substituted heterocyclic group with a nitrogen atom at the 1-position;

[0025] X 11 Each of these terms independently represents hydrogen, alkyl, alkenyl, ynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclic, heterocyclic alkyl, aryl, or arylalkyl, wherein the terms "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclic", "heterocyclic alkyl", "aryl", or "arylalkyl" are independently unsubstituted or selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-alkyl-(CO)OR 14 The ring is substituted by at least one group, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0026] X 12 Each of these terms independently represents alkyl, alkenyl, ynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclic, heterocyclic alkyl, aryl, or arylalkyl, wherein the terms "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclic", "heterocyclic alkyl", "aryl", or "arylalkyl" are independently unsubstituted or selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-alkyl-(CO)OR 14 The ring is substituted by at least one group, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0027] X 13 X 14 Each of these groups independently represents hydrogen, halogen, cyano, alkoxy, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, alkyl, alkenyl, ynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclic or heterocyclic alkyl, or the group CX. 13 X14 Together they form unsubstituted or substituted cyclic structures, or groups NX. 13 X 14 Together they form an unsubstituted or substituted heterocyclic group with a nitrogen atom at the 1-position, wherein the "alkyl", "alkenyl" or "alkynyl" is independently unsubstituted or halogenated, and the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "aryl", "arylalkyl", "heterocyclic" or "heterocyclic alkyl" is independently unsubstituted or halogenated from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-alkyl-(CO)OR 14 The ring is substituted by at least one group, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0028] R 11 Each of the following groups independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl, or benzyl, wherein the "alkyl", "alkenyl", or "alkynyl" group is independently unsubstituted or substituted with a halogen, and the "phenyl" or "benzyl" group is independently unsubstituted or substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, or haloalkoxy.

[0029] R 12 Each of these can independently represent hydrogen, alkyl, alkenyl, alkynyl, alkoxy, alkylsulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl, or -(CO)N(R) 12 )2 or -(SO2)N(R 12 The group N(R) in )2 12 )2 represent, independently, unsubstituted or substituted heterocyclic groups with a nitrogen atom at the 1-position;

[0030] R 13 Each of the following groups independently represents an alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, or a phenyl group substituted with at least one of the following groups: halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, alkylthio, alkylsulfonyl, or a phenoxy group substituted with at least one of the following groups: halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, or haloalkoxy.

[0031] R 14 Each of these groups independently represents hydrogen, alkyl, haloalkyl, phenyl, or a phenyl group substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, or haloalkoxy.

[0032] m represents 0 or 1.

[0033] In one specific embodiment, Y represents halogen, halogenated C1-C8 alkyl, cyano, nitro, or amino.

[0034] In another specific embodiment, Y represents halogen, halogenated C1-C6 alkyl, cyano, nitro, or amino.

[0035] In one specific embodiment, R1, R2, R3, R4, and R5 independently represent hydrogen, halogen, hydroxyl, mercapto, formyl, hydroxyl C1-C8 alkyl, nitro, cyano, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, and -OR, respectively. 11 -SR 11 -(SO)R 11 -(SO2)R 11 -(SO2)OR 11 -O(SO2)R 11 -N(R) 12 2. Phenyl or benzyl, wherein,

[0036] The “C1-C8 alkyl”, “C2-C8 alkenyl”, “C2-C8 alkynyl”, “C3-C8 cycloalkyl”, “C3-C8 cycloalkyl C1-C8 alkyl”, “C3-C8 cycloalkenyl” or “C3-C8 cycloalkenyl C1-C8 alkyl” are each independently unsubstituted or substituted with a halogen, and the “phenyl” or “benzyl” are each independently unsubstituted or substituted with at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halo-C1-C8 alkoxy.

[0037] In another specific embodiment, R1, R2, R3, R4, and R5 independently represent hydrogen, halogen, hydroxyl, mercapto, formyl, hydroxyl C1-C6 alkyl, nitro, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, and -OR. 11-SR 11 -(SO)R 11 -(SO2)R 11 -(SO2)OR 11 -O(SO2)R 11 -N(R) 12 2. Phenyl or benzyl, wherein,

[0038] The “C1-C6 alkyl”, “C2-C6 alkenyl”, “C2-C6 alkynyl”, “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C6 alkyl”, “C3-C6 cycloalkenyl” or “C3-C6 cycloalkenyl C1-C6 alkyl” are each independently unsubstituted or substituted with halogens, and the “phenyl” or “benzyl” are each independently unsubstituted or substituted with one, two or three groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxy carbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halo-C1-C6 alkoxy.

[0039] In another specific embodiment, R1, R2, R3, R4, and R5 independently represent hydrogen, halogen, hydroxyl, mercapto, formyl, hydroxyl C1-C6 alkyl, nitro, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, and -OR. 11 -SR 11 -(SO)R 11 -(SO2)R 11 -(SO2)OR 11 -O(SO2)R 11 -N(R) 12 2. Phenyl or benzyl, wherein,

[0040] The “C1-C6 alkyl”, “C2-C6 alkenyl”, “C2-C6 alkynyl”, “C3-C6 cycloalkyl”, “C3-C6 cycloalkylC1-C3 alkyl”, “C3-C6 cycloalkenyl” or “C3-C6 cycloalkenylC1-C3 alkyl” are each independently unsubstituted or substituted with halogens, and the “phenyl” or “benzyl” are each independently unsubstituted or substituted with one, two or three groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halo-C1-C6 alkoxy.

[0041] In one specific embodiment, X1, X2, X3, and X4 independently represent hydrogen, halogen, nitro, cyano, cyanothio, hydroxyl, mercapto, sulfonic acid, formyl, haloformyl, azide, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, -PO(OR')2, -OR”, -(CO)R”, -SR”, -(SO)R”, -(SO2)R”, -Si(R”)3, -O(CO)R”, -O-(SO2)R”, -S(CO)R”, -(SO2)OR”, -O(CO)OR”, -(CO)(CO)OR”. -CR'=N-OH, -CR'=NOR", heterocyclic group, heterocyclic C1-C8 alkyl, aryl, aryl C1-C8 alkyl, amino, amino C1-C8 alkyl, amino carbonyl C1-C8 alkyl, amino carbonyloxy C1-C8 alkyl, amino thiocarbonyloxy C1-C8 alkyl, amino sulfonyl or amino sulfonyloxy C1-C8 alkyl, wherein,

[0042] The "C1-C8 alkyl", "C2-C8 alkenyl", or "C2-C8 alkynyl" groups are independently unsubstituted or substituted by at least one group selected from halogen, cyano, hydroxyl, mercapto, carboxyl, -OR", -(CO)R", -SR", -(SO2)R", -O(CO)H, -O(CO)R", -O-(SO2)R", -(CO)OR", -O(CO)OR", -O(CO)(CO)OH, -O(CO)(CO)OR", -O-(C1-C8 alkyl)-(CO)OH, or -O-(C1-C8 alkyl)-(CO)OR.

[0043] The terms “C3-C8 cycloalkyl,” “C3-C8 cycloalkyl C1-C8 alkyl,” “C3-C8 cycloalkenyl,” “C3-C8 cycloalkenyl C1-C8 alkyl,” “heterocyclic,” “heterocyclic C1-C8 alkyl,” “aryl,” or “aryl C1-C8 alkyl” are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 ynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-(C1-C8 alkyl)-(CO)OR14 The ring is substituted by at least one group, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0044] The "amino", "aminoC1-C8 alkyl", "aminocarbonylC1-C8 alkyl", "aminocarbonyloxyC1-C8 alkyl", "aminothiocarbonyloxyC1-C8 alkyl", "aminosulfonyl" or "aminosulfonyloxyC1-C8 alkyl" are each independently unsubstituted or selected from -R 11 -OR 11 -(CO)R 11 -(CO)OR 11 -(C1-C8 alkyl)-(CO)OR 11 -(SO2)R 11 -(SO2)OR 11 -(C1-C8 alkyl)-(SO2)R 11 -(CO)N(R) 12 )2 or -(SO2)N(R 12 Substituted by one or two groups of )2;

[0045] R' independently represents hydrogen, halogen, C1-C8 alkoxy, C1-C8 alkoxy-C1-C8 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl-C1-C8 alkyl, aryl, aryl-C1-C8 alkyl, heterocyclic, or heterocyclic-C1-C8 alkyl, wherein the "C1-C8 alkyl", "C2-C8 alkenyl", or "C2-C8 alkynyl" are independently unsubstituted or halogen-substituted, and the "C3-C8 cycloalkyl" is... "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "aryl", "aryl C1-C8 alkyl", "heterocyclic" or "heterocyclic C1-C8 alkyl" are, independently, unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 ynyl, halo-C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-(C1-C8 alkyl)-(CO)OR14 The ring is substituted by at least one group, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0046] "R" independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, aryl C2-C8 alkenyl, heterocyclic, heterocyclic C1-C8 alkyl, or heterocyclic C2-C8 alkenyl, wherein the "C1-C8 alkyl", "C2-C8 alkenyl", or "C2-C8 ynyl" is independently unsubstituted or selected from halogen, cyano, triC1-C8 alkylsilyl, -OR 13 -SR 13 -O(CO)R 13 -(CO)R 13 -(CO)OR 13 OR-O(CO)OR 13 The "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "aryl", "aryl C1-C8 alkyl", "aryl C2-C8 alkenyl", "heterocyclic", "heterocyclic C1-C8 alkyl" or "heterocyclic C2-C8 alkenyl" are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 ynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-(C1-C8 alkyl)-(CO)OR 14 It is a fused ring formed by replacing at least one group in the ring, or by two adjacent carbon atoms on the ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0047] In another specific embodiment, X1, X2, X3, and X4 independently represent hydrogen, halogen, nitro, cyano, cyanothio, hydroxyl, mercapto, sulfonic acid, formyl, haloformyl, azide, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, -PO(OR')2, -OR”, -(CO)R”, -SR”, -(SO)R”, -(SO2)R”, -Si(R”)3, -O(CO)R”, -O-(SO2)R”, -S(CO)R”, -(SO2)OR”, -O(CO)OR”, -(CO)(CO)OR”. -CR'=N-OH, -CR'=NOR", heterocyclic group, heterocyclic C1-C6 alkyl, aryl, aryl C1-C6 alkyl, amino, amino C1-C6 alkyl, amino carbonyl C1-C6 alkyl, amino carbonyloxy C1-C6 alkyl, amino thiocarbonyloxy C1-C6 alkyl, amino sulfonyl or amino sulfonyloxy C1-C6 alkyl, wherein,

[0048] The "C1-C6 alkyl", "C2-C6 alkenyl", or "C2-C6 alkynyl" groups are independently unsubstituted or substituted by one, two, or three groups selected from halogen, cyano, hydroxyl, mercapto, carboxyl, -OR", -(CO)R", -SR", -(SO2)R", -O(CO)H, -O(CO)R", -O-(SO2)R", -(CO)OR", -O(CO)OR", -O(CO)(CO)OH, -O(CO)(CO)OR", -O-(C1-C6 alkyl)-(CO)OH, or -O-(C1-C6 alkyl)-(CO)OR".

[0049] The terms “C3-C6 cycloalkyl,” “C3-C6 cycloalkylC1-C6 alkyl,” “C3-C6 cycloalkenyl,” “C3-C6 cycloalkenylC1-C6 alkyl,” “heterocyclic,” “heterocyclic C1-C6 alkyl,” “aryl,” or “aryl C1-C6 alkyl” are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 ynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-(C1-C6 alkyl)-(CO)OR14 One, two, or three groups in the ring are substituted, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0050] The "amino", "aminoC1-C6 alkyl", "aminocarbonylC1-C6 alkyl", "aminocarbonyloxyC1-C6 alkyl", "aminothiocarbonyloxyC1-C6 alkyl", "aminosulfonyl" or "aminosulfonyloxyC1-C6 alkyl" are each independently unsubstituted or selected from -R 11 -OR 11 -(CO)R 11 -(CO)OR 11 -(C1-C6 alkyl)-(CO)OR 11 -(SO2)R 11 -(SO2)OR 11 -(C1-C6 alkyl)-(SO2)R 11 -(CO)N(R) 12 )2 or -(SO2)N(R 12 Substituted by one or two groups of )2;

[0051] R' independently represents hydrogen, halogen, C1-C6 alkoxy, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl-C1-C6 alkyl, aryl, aryl-C1-C6 alkyl, heterocyclic, or heterocyclic-C1-C6 alkyl, wherein the "C1-C6 alkyl", "C2-C6 alkenyl", or "C2-C6 ynyl" are independently unsubstituted or halogen-substituted, and the "C3-C6 cycloalkyl" is... "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "aryl", "aryl C1-C6 alkyl", "heterocyclic" or "heterocyclic C1-C6 alkyl" are, independently, unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 ynyl, halo-C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-(C1-C6 alkyl)-(CO)OR14 One, two or three groups in the ring are replaced, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0052] "R" independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, aryl C2-C6 alkenyl, heterocyclic, heterocyclic C1-C6 alkyl, or heterocyclic C2-C6 alkenyl, wherein the "C1-C6 alkyl", "C2-C6 alkenyl", or "C2-C6 ynyl" is independently unsubstituted or selected from halogen, cyano, triC1-C6 alkylsilyl, -OR 13 -SR 13 -O(CO)R 13 -(CO)R 13 -(CO)OR 13 OR-O(CO)OR 13 The "C3-C6 cycloalkyl", "C3-C6 cycloalkyl-C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl-C1-C6 alkyl", "aryl", "aryl-C1-C6 alkyl", "aryl-C2-C6 alkenyl", "heterocyclic", "heterocyclic-C1-C6 alkyl" or "heterocyclic-C2-C6 alkenyl" are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 ynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-(C1-C6 alkyl)-(CO)OR 14 It is a fused ring formed by replacing one, two or three groups in the ring, or by two adjacent carbon atoms on the ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0053] In another specific embodiment, X1, X2, X3, and X4 independently represent hydrogen, halogen, nitro, cyano, cyanothio, hydroxyl, mercapto, sulfonic acid, formyl, haloformyl, azide, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C3 alkyl, -PO(OR')2, -OR”, -(CO)R”, -SR”, -(SO)R”, -(SO2)R”, -Si(R”)3, -O(CO)R”, -O-(SO2)R”, -S(CO)R”, -(SO2)OR”, -O(CO)OR”, -(CO)(CO)OR”. -CR'=N-OH, -CR'=NOR", heterocyclic group, heterocyclic C1-C3 alkyl, aryl, aryl C1-C3 alkyl, amino, amino C1-C3 alkyl, amino carbonyl C1-C3 alkyl, amino carbonyloxy C1-C3 alkyl, amino thiocarbonyloxy C1-C3 alkyl, amino sulfonyl or amino sulfonyloxy C1-C3 alkyl, wherein,

[0054] The "C1-C6 alkyl", "C2-C6 alkenyl", or "C2-C6 alkynyl" groups are independently unsubstituted or substituted by one, two, or three groups selected from halogen, cyano, hydroxyl, mercapto, carboxyl, -OR", -(CO)R", -SR", -(SO2)R", -O(CO)H, -O(CO)R", -O-(SO2)R", -(CO)OR", -O(CO)OR", -O(CO)(CO)OH, -O(CO)(CO)OR", -O-(C1-C3 alkyl)-(CO)OH, or -O-(C1-C3 alkyl)-(CO)OR.

[0055] The terms “C3-C6 cycloalkyl,” “C3-C6 cycloalkylC1-C3 alkyl,” “C3-C6 cycloalkenyl,” “C3-C6 cycloalkenylC1-C3 alkyl,” “heterocyclic,” “heterocyclic C1-C3 alkyl,” “aryl,” or “aryl C1-C3 alkyl” are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 ynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-(C1-C3 alkyl)-(CO)OR14 One, two, or three groups in the ring are substituted, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0056] The terms "amino", "aminoC1-C3alkyl", "aminocarbonylC1-C3alkyl", "aminocarbonyloxyC1-C3alkyl", "aminothiocarbonyloxyC1-C3alkyl", "aminosulfonyl" or "aminosulfonyloxyC1-C3alkyl" are each independently unsubstituted or selected from -R 11 -OR 11 -(CO)R 11 -(CO)OR 11 -(C1-C3 alkyl)-(CO)OR 11 -(SO2)R 11 -(SO2)OR 11 -(C1-C3 alkyl)-(SO2)R 11 -(CO)N(R) 12 )2 or -(SO2)N(R 12 Substituted by one or two groups of )2;

[0057] R' independently represents hydrogen, halogen, C1-C6 alkoxy, C1-C6 alkoxy-C1-C3 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl-C1-C3 alkyl, aryl, aryl-C1-C3 alkyl, heterocyclic, or heterocyclic-C1-C3 alkyl, wherein the "C1-C6 alkyl", "C2-C6 alkenyl", or "C2-C6 ynyl" are independently unsubstituted or halogen-substituted, and the "C3-C6 cycloalkyl" is... "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C3 alkyl", "aryl", "aryl C1-C3 alkyl", "heterocyclic" or "heterocyclic C1-C3 alkyl" are, independently, unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 ynyl, halo-C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-(C1-C3 alkyl)-(CO)OR14 One, two or three groups in the ring are replaced, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0058] "R" independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, aryl, aryl C1-C3 alkyl, aryl C2-C3 alkenyl, heterocyclic, heterocyclic C1-C3 alkyl, or heterocyclic C2-C3 alkenyl, wherein the "C1-C6 alkyl", "C2-C6 alkenyl", or "C2-C6 ynyl" is independently unsubstituted or selected from halogen, cyano, triC1-C6 alkylsilyl, -OR 13 -SR 13 -O(CO)R 13 -(CO)R 13 -(CO)OR 13 OR-O(CO)OR 13 The "C3-C6 cycloalkyl", "C3-C6 cycloalkylC1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenylC1-C3 alkyl", "aryl", "aryl C1-C3 alkyl", "aryl C2-C3 alkenyl", "heterocyclic", "heterocyclic C1-C3 alkyl", or "heterocyclic C2-C3 alkenyl" are each independently unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 ynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-(C1-C3 alkyl)-(CO)OR 14 It is a fused ring formed by replacing one, two or three groups in the ring, or by two adjacent carbon atoms on the ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0059] In one specific embodiment, W3 independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclic, aryl, etc. , , , or Wherein, the “C1-C8 alkyl,” “C2-C8 alkenyl,” or “C2-C8 alkynyl” are independently unsubstituted or selected from halogens, cyano, nitro, C3-C8 cycloalkyl, triC1-C8 alkylsilyl, C3-C8 cycloalkenyl, heterocyclic, aryl, , , , , , , , or The "C3-C8 cycloalkyl", "C3-C8 cycloalkenyl", "heterocyclic" or "aryl" group is substituted by at least one group, wherein the "C3-C8 cycloalkyl", "C3-C8 cycloalkenyl", "heterocyclic" or "aryl" group is independently unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 ynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-(C1-C8 alkyl)-(CO)OR 14 The ring is substituted by at least one group, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0060] W4 and W5 independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclic, aryl, and so on. , , , , , , , or Wherein, the “C1-C8 alkyl,” “C2-C8 alkenyl,” or “C2-C8 alkynyl” are independently unsubstituted or selected from halogens, cyano, nitro, C3-C8 cycloalkyl, triC1-C8 alkylsilyl, C3-C8 cycloalkenyl, heterocyclic, aryl, , , , , , , , or The "C3-C8 cycloalkyl", "C3-C8 cycloalkenyl", "heterocyclic" or "aryl" group is substituted by at least one group, wherein the "C3-C8 cycloalkyl", "C3-C8 cycloalkenyl", "heterocyclic" or "aryl" group is independently unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 ynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-(C1-C8 alkyl)-(CO)OR 14 The ring is substituted by at least one group, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0061] Or NW4W5 represents ;or , , , or It is either unsubstituted or substituted by at least one group selected from oxo, C1-C8 alkyl or C1-C8 alkoxycarbonyl;

[0062] X 11 Each of these terms independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclic, heterocyclic C1-C8 alkyl, aryl, or aryl C1-C8 alkyl, wherein the terms "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", and "C3-C8 cycloalkenyl C1-C8 alkyl" are used to represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkenyl C1-C8 alkyl ... "1-C8 alkyl", "heterocyclic", "heterocyclic C1-C8 alkyl", "aryl", or "aryl C1-C8 alkyl" are, independently, unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 ynyl, halo-C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14-N(R) 14 )2 or -O-(C1-C8 alkyl)-(CO)OR 14 The ring is substituted by at least one group, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0063] X 12 Each of these groups independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclic, heterocyclic C1-C8 alkyl, aryl, or aryl C1-C8 alkyl, wherein the terms "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", and "C3-C8 cycloalkenyl C1-C8 alkyl" are used to represent C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkenyl C1-C8 alkyl, C3-C8 cycloalkenyl, and C3-C8 cycloalkenyl C1-C8 alkyl. "-C8 alkyl", "heterocyclic", "heterocyclic C1-C8 alkyl", "aryl" or "aryl C1-C8 alkyl" are, independently, unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 ynyl, halo-C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-(C1-C8 alkyl)-(CO)OR 14 The ring is substituted by at least one group, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0064] X 13 X 14 Each of these groups independently represents hydrogen, halogen, cyano, C1-C8 alkoxy, C1-C8 alkoxy-C1-C8 alkyl, C1-C8 alkyl carbonyl, C1-C8 alkoxy carbonyl, C1-C8 alkyl sulfonyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl-C1-C8 alkyl, aryl, aryl-C1-C8 alkyl, heterocyclic or heterocyclic C1-C8 alkyl, or the group CX. 13 X 14 Together they form 5- to 8-membered carbon rings or heterocycles containing oxygen, sulfur, or nitrogen, or the NX group. 13 X 14 Together , , , or Wherein, the “C1-C8 alkyl,” “C2-C8 alkenyl,” or “C2-C8 alkynyl” are independently unsubstituted or halogenated, respectively; and the “C3-C8 cycloalkyl,” “C3-C8 cycloalkyl C1-C8 alkyl,” “C3-C8 cycloalkenyl,” “C3-C8 cycloalkenyl C1-C8 alkyl,” “aryl,” “aryl C1-C8 alkyl,” “heterocyclic,” or “heterocyclic C1-C8 alkyl” are independently unsubstituted or substituted with a compound selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-(C1-C8 alkyl)-(CO)OR 14 The ring is substituted by at least one group, or two adjacent carbon atoms on the ring form a fused ring with an unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O- group, wherein the "5- to 8-membered carbon ring or oxygen-, sulfur-, or nitrogen-containing heterocycle" is unsubstituted or substituted by at least one group selected from C1-C8 alkyl, C1-C8 alkoxycarbonyl, or benzyl, or forms a fused ring structure with an aryl or heterocyclic group; the " , , , or "is unsubstituted or substituted by at least one group selected from oxo, C1-C8 alkyl or C1-C8 alkoxycarbonyl".

[0065] In another specific embodiment, W3 independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclic, aryl, etc. , , , or Wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” or “C2-C6 alkynyl” are independently unsubstituted or selected from halogen, cyano, nitro, C3-C6 cycloalkyl, triC1-C6 alkylsilyl, C3-C6 cycloalkenyl, heterocyclic, aryl, , , , , , , , or The "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclic", or "aryl" groups are substituted by one, two, or three groups, wherein the "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclic", or "aryl" group is independently unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 ynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-(C1-C6 alkyl)-(CO)OR 14 One, two or three groups in the ring are replaced, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0066] W4 and W5 independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclic, aryl, and so on. , , , , , , , or Wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” or “C2-C6 alkynyl” are independently unsubstituted or selected from halogen, cyano, nitro, C3-C6 cycloalkyl, triC1-C6 alkylsilyl, C3-C6 cycloalkenyl, heterocyclic, aryl, , , , , , , , or The "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclic", or "aryl" groups are substituted by one, two, or three groups, wherein the "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclic", or "aryl" group is independently unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 ynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-(C1-C6 alkyl)-(CO)OR 14 One, two or three groups in the ring are replaced, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0067] Or NW4W5 represents ;or , , , or It is either unsubstituted or substituted by one, two or three groups selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl;

[0068] X 11 Each of these terms independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclic, heterocyclic C1-C6 alkyl, aryl, or aryl C1-C6 alkyl, wherein the terms "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", and "C3-C6 cycloalkenyl C1-C6 alkyl" are used to represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl, C3-C6 cycloalkyl ... "1-C6 alkyl", "heterocyclic", "heterocyclic C1-C6 alkyl", "aryl" or "aryl C1-C6 alkyl" are, independently, unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 ynyl, halo-C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14)2 or -O-(C1-C6 alkyl)-(CO)OR 14 One, two or three groups in the ring are replaced, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0069] X 12 Each of these groups independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclic, heterocyclic C1-C6 alkyl, aryl, or aryl C1-C6 alkyl, wherein the terms "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", and "C3-C6 cycloalkenyl C1-C6 alkyl" are used interchangeably with "C3-C6 cycloalkyl". "-C6 alkyl", "heterocyclic", "heterocyclic C1-C6 alkyl", "aryl" or "aryl C1-C6 alkyl" are, independently, unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 ynyl, halo-C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-(C1-C6 alkyl)-(CO)OR 14 One, two or three groups in the ring are replaced, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0070] X 13 X 14 Each of these groups independently represents hydrogen, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkyl sulfonyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl-C1-C6 alkyl, aryl, aryl-C1-C6 alkyl, heterocyclic or heterocyclic C1-C6 alkyl, or the group CX. 13 X 14 Together they form 5-8 member saturated carbon rings, or , or the NX group 13 X 14 Together , , , or Wherein, the “C1-C6 alkyl,” “C2-C6 alkenyl,” or “C2-C6 alkynyl” are independently unsubstituted or halogenated, respectively; and the “C3-C6 cycloalkyl,” “C3-C6 cycloalkyl C1-C6 alkyl,” “C3-C6 cycloalkenyl,” “C3-C6 cycloalkenyl C1-C6 alkyl,” “aryl,” “aryl C1-C6 alkyl,” “heterocyclic,” or “heterocyclic C1-C6 alkyl” are independently unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-(C1-C6 alkyl)-(CO)OR 14 The ring is substituted by one, two, or three groups, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-, wherein the "5- to 8-membered saturated carbon ring" refers to a 5- to 8-membered saturated carbon ring. or "is unsubstituted or substituted with one, two, or three groups selected from C1-C6 alkyl, C1-C6 alkoxycarbonyl, or benzyl, or forms a fused ring structure with an aryl or heterocyclic group, wherein the " , , , or "It is either unsubstituted or substituted by one, two or three groups selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl".

[0071] In another specific embodiment, W3 independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclic, aryl, etc. , , , or Wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” or “C2-C6 alkynyl” are independently unsubstituted or selected from halogen, cyano, nitro, C3-C6 cycloalkyl, triC1-C6 alkylsilyl, C3-C6 cycloalkenyl, heterocyclic, aryl, , , , , , , , or The "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclic", or "aryl" groups are substituted by one, two, or three groups, wherein the "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclic", or "aryl" group is independently unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 ynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-(C1-C3 alkyl)-(CO)OR 14 One, two or three groups in the ring are replaced, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0072] W4 and W5 independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclic, aryl, and so on. , , , , , , , or Wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” or “C2-C6 alkynyl” are independently unsubstituted or selected from halogen, cyano, nitro, C3-C6 cycloalkyl, triC1-C6 alkylsilyl, C3-C6 cycloalkenyl, heterocyclic, aryl, , , , , , , , or The "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclic", or "aryl" groups are substituted by one, two, or three groups, wherein the "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclic", or "aryl" group is independently unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 ynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-(C1-C3 alkyl)-(CO)OR 14 One, two or three groups in the ring are replaced, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0073] Or NW4W5 represents ;or , , , or It is either unsubstituted or substituted by one, two or three groups selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl;

[0074] X 11 Each of these groups independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclic, heterocyclic C1-C3 alkyl, aryl, or aryl C1-C3 alkyl, wherein the terms "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloalkenyl", and "C3-C6 cycloalkenyl C1-C3 alkyl" are used interchangeably with "C3-C6 cycloalkyl". "1-C3 alkyl", "heterocyclic", "heterocyclic C1-C3 alkyl", "aryl", or "aryl C1-C3 alkyl" are, independently, unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 ynyl, halo-C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14)2 or -O-(C1-C3 alkyl)-(CO)OR 14 One, two or three groups in the ring are replaced, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0075] X 12 Each of these groups independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclic, heterocyclic C1-C3 alkyl, aryl, or aryl C1-C3 alkyl, wherein the terms "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloalkenyl", and "C3-C6 cycloalkenyl C1-C3 alkyl" are used interchangeably with "C3-C6 cycloalkyl". "-C3 alkyl", "heterocyclic", "heterocyclic C1-C3 alkyl", "aryl" or "aryl C1-C3 alkyl" are, independently, unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 ynyl, halo-C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-(C1-C3 alkyl)-(CO)OR 14 One, two or three groups in the ring are replaced, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-.

[0076] X 13 X 14 Each of these groups independently represents hydrogen, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxy-C1-C3 alkyl, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkyl sulfonyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl-C1-C3 alkyl, aryl, aryl-C1-C3 alkyl, heterocyclic or heterocyclic C1-C3 alkyl, or the group CX. 13 X 14 Together they form 5-8 member saturated carbon rings, or , or the NX group 13 X 14 Together , , , or Wherein, the “C1-C6 alkyl,” “C2-C6 alkenyl,” or “C2-C6 alkynyl” are independently unsubstituted or halogenated, respectively; and the “C3-C6 cycloalkyl,” “C3-C6 cycloalkyl C1-C3 alkyl,” “C3-C6 cycloalkenyl,” “C3-C6 cycloalkenyl C1-C3 alkyl,” “aryl,” “aryl C1-C3 alkyl,” “heterocyclic,” or “heterocyclic C1-C3 alkyl” are independently unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 14 -SR 14 -(CO)OR 14 -(SO2)R 14 -N(R) 14 )2 or -O-(C1-C3 alkyl)-(CO)OR 14 The ring is substituted by one, two, or three groups, or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2CH2- or -OCH2O-, wherein the "5- to 8-membered saturated carbon ring" refers to a 5- to 8-membered saturated carbon ring. or "is unsubstituted or substituted with one, two, or three groups selected from C1-C6 alkyl, C1-C6 alkoxycarbonyl, or benzyl, or forms a fused ring structure with phenyl or thiophene;" , , , or "It is either unsubstituted or substituted by one, two or three groups selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl".

[0077] In one specific implementation, R 11Each of the following groups independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, phenyl, or benzyl, wherein the "C1-C8 alkyl", "C2-C8 alkenyl", or "C2-C8 alkynyl" is independently unsubstituted or substituted with a halogen, and the "phenyl" or "benzyl" is independently unsubstituted or substituted with at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy, or halo-C1-C8 alkoxy;

[0078] R 12 Each of these can independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylsulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl or C3-C8 cycloalkenylC1-C8 alkyl, or -(CO)N(R) 12 )2 or -(SO2)N(R 12 The group N(R) in )2 12 )2 represent independently , , , or It is either unsubstituted or substituted by at least one group selected from oxo, C1-C8 alkyl or C1-C8 alkoxycarbonyl;

[0079] R 13 Each of the following groups independently represents a C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, phenyl, or a phenyl group substituted with at least one of the following groups: halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxy, halo-C1-C8 alkoxy, C1-C8 alkoxy carbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, or a phenoxy group substituted with at least one of the following groups: halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxy, or halo-C1-C8 alkoxy;

[0080] R 14 Each of these groups independently represents hydrogen, C1-C8 alkyl, halo-C1-C8 alkyl, phenyl, or a phenyl group substituted with at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy, or halo-C1-C8 alkoxy.

[0081] In another specific implementation, R 11 Each of the following groups independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, phenyl, or benzyl, wherein the "C1-C6 alkyl", "C2-C6 alkenyl", or "C2-C6 alkynyl" is independently unsubstituted or substituted with a halogen, and the "phenyl" or "benzyl" is independently unsubstituted or substituted with one, two, or three groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy, or halo-C1-C6 alkoxy.

[0082] R 12 Each of these can independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl or C3-C6 cycloalkenylC1-C6 alkyl, or -(CO)N(R) 12 )2 or -(SO2)N(R 12 The group N(R) in )2 12 )2 represent independently , , , or It is either unsubstituted or substituted by one, two or three groups selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl;

[0083] R 13 Each of the following groups independently represents a C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, phenyl, or a phenyl group substituted with one, two, or three of the following groups: halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxy, halo-C1-C6 alkoxy, C1-C6 alkoxy carbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, or a phenoxy group substituted with one, two, or three of the following groups: halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxy, or halo-C1-C6 alkoxy.

[0084] R 14Each of these groups independently represents hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, phenyl, or a phenyl group substituted with one, two, or three groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy, or halo-C1-C6 alkoxy.

[0085] In another specific implementation, R 11 Each of the following groups independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C3 alkyl, phenyl, and benzyl, wherein the "C1-C6 alkyl", "C2-C6 alkenyl", or "C2-C6 alkynyl" is independently unsubstituted or substituted with a halogen, and the "phenyl" or "benzyl" is independently unsubstituted or substituted with one, two, or three groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy, or halo-C1-C6 alkoxy.

[0086] R 12 Each of these can independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkoxy, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C3 alkyl, C3-C6 cycloalkenyl or C3-C6 cycloalkenylC1-C3 alkyl, or -(CO)N(R) 12 )2 or -(SO2)N(R 12 The group N(R) in )2 12 )2 represent independently , , , or It is either unsubstituted or substituted by one, two or three groups selected from oxo, C1-C6 alkyl or C1-C6 alkoxycarbonyl;

[0087] R 13Each of the following groups independently represents a C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, phenyl, or a phenyl group substituted with one, two, or three of the following groups: halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxy, halo-C1-C6 alkoxy, C1-C6 alkoxy carbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, or a phenoxy group substituted with one, two, or three of the following groups: halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxy, or halo-C1-C6 alkoxy.

[0088] R 14 Each of these groups independently represents hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, phenyl, or a phenyl group substituted with one, two, or three groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy, or halo-C1-C6 alkoxy.

[0089] In the definitions of compounds shown in the above general formulas and in all the following structural formulas, the technical terms used, whether alone or in compound terms, represent the following substituents: alkyl groups having more than two carbon atoms can be straight-chain or branched. For example, the compound term "-alkyl-(CO)OR". 11 The alkyl group can be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, etc. The alkyl group is, for example, C1 alkyl-methyl; C2 alkyl-ethyl; C3 alkyl-propyl such as n-propyl or isopropyl; C4 alkyl-butyl such as n-butyl, isobutyl, tert-butyl, or 2-butyl; C5 alkyl-pentyl such as n-pentyl; C6 alkyl-hexyl such as n-hexyl, isohexyl, and 1,3-dimethylbutyl. Similarly, the alkenyl group is, for example, vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl. Cycloalkyl is a carbocyclic saturated ring system having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. Similarly, cycloalkenyl is a monocyclic alkenyl group having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl, wherein the double bond can be in any position. Halogens are fluorine, chlorine, bromine, or iodine.

[0090] Unless otherwise specified, the term "aryl" in this invention includes, but is not limited to, phenyl, naphthyl, and... , The "heterocyclic group" mentioned includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups. , , , , , , , , , , , , , , , , , or And, including but not limited to, heteroaryl groups, i.e., aromatic cyclic groups containing, for example, 3 to 6 ring atoms and optionally fused with benzo[a] rings, wherein 1 to 4 (e.g., 1, 2, 3, or 4) heteroatoms are selected from oxygen, nitrogen, and sulfur, for example , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , or .

[0091] If a group is substituted by another group, this should be understood to mean that the group is substituted by one or more identical or different groups selected from those groups mentioned. Furthermore, the identical or different substitution characters contained in the identical or different substituents are chosen independently and may be identical or different. This also applies to ring systems formed from different atoms and units. Meanwhile, the scope of the claims excludes compounds that are chemically unstable under standard conditions, as known to those skilled in the art.

[0092] Furthermore, unless otherwise specified, the phrase "replaced by at least one group" in this invention refers to being replaced by, for example, 1, 2, 3, 4, or 5 groups; groups without specific attachment positions (including heterocyclic groups, aryl groups, etc.) can be attached at any position, including positions attached to C or N; if it is substituted, the substituent can also be substituted at any position, as long as it conforms to the rules of chemical bond attachment. For example, a heteroaryl group substituted by one methyl group. , can represent , , , wait.

[0093] It should be noted that when general formula I When the carbon atom (C*) bonded to X1 and X2 is a chiral center (i.e., when X1 and X2 are not the same), it has an R configuration or an S configuration.

[0094] In this invention, the stereochemical configuration at the position marked * in Formula I is determined to be predominantly (R) or (S) according to the Cahn-Ingold-Prelog system; however, the subject matter of this invention also relates to all stereoisomers at other positions included in Formula I, and mixtures thereof. Such Formula I compounds contain, for example, one or more additional asymmetric carbon atoms or other double bonds not specifically described in Formula I. It should be understood that this invention includes pure isomers and mixtures thereof enriched to varying degrees with pure isomers, wherein the asymmetric carbon atom at the position marked * is in R-configuration or S-configuration, or in the mixture, the compound or a compound with the same chemical structure has R-configuration or S-configuration at the position marked *, or is present in a proportion predominantly having R-configuration or S-configuration (at least 60% R-configuration or S-configuration), while other asymmetric carbon atoms may be present in racemic form or may be resolved to varying degrees. Possible stereoisomers defined by a specific spatial form, such as enantiomers, diastereomers, Z- and E-isomers, are included in Formula I, provided that the stereochemical configuration conditions at the position marked as * are met. They can be obtained from mixtures of stereoisomers by conventional methods or prepared by stereoselective reactions in conjunction with stereochemically pure initial substances.

[0095] If various functional groups are present, the present invention also includes any ketone and enol tautomer forms, mixtures thereof, and salts thereof.

[0096] Stereoisomers can be obtained from mixtures prepared by optical resolution. Similarly, stereoisomers can be selectively prepared using stereoselective reactions and optically active starting materials and / or auxiliaries. For optical resolution, conventional methods (see Textbooks of Stereochemistry) can generally be used, such as physical methods for resolving mixtures into diastereomers, including crystallization, chromatography, especially column chromatography and high-performance liquid chromatography, distillation under reduced pressure as needed, extraction, and other methods, typically employing chromatographic separation on a chiral solid phase, which can separate the residual mixture of enantiomers. Suitable for preparative or industrial scales are methods such as crystallizing diastereomers, which can be obtained from the compound using optically active acids, and, if acidic groups are present, using optically active bases as needed.

[0097] The method for preparing the heterocyclic substituted aromatic compound includes the following steps:

[0098] The compound represented by general formula II is reacted with the compound represented by general formula III to produce the compound represented by general formula I. The chemical reaction equation is as follows:

[0099]

[0100] Wherein, Hal represents a halogen, preferably Cl; the definitions of substituents X1, X2, R1, R2, R3, R4, M1, M2, Q, Y and Z are as described above;

[0101] Preferably, the reaction is carried out in the presence of a base and a solvent; more preferably, the base is selected from at least one of nitrogen-containing bases (such as C1-C6 alkylamines, preferably tri-(C1-C6)-alkylamines, for example triethylamine, trimethylamine, N-ethyldiisopropylamine);

[0102] The solvent is selected from at least one of aromatic hydrocarbons (such as benzene, chlorobenzene, toluene, cresol or o-, m- and p-xylene), THF, DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, dioxane, dichloromethane, toluene or ethyl acetate.

[0103] Compounds represented by general formula II can be prepared by the methods shown in WO12130798, WO1404882, WO14048882, WO18228985, WO18228986, WO19034602 or WO19145245.

[0104] A herbicide composition comprising at least one of the heterocyclic substituted aromatic compounds in an herbicidal effective amount, preferably further comprising a formulation adjuvant.

[0105] A method for controlling weeds, comprising applying a herbicidal amount of at least one of the heterocyclic substituted aromatic compounds or the herbicide composition to plants or weedy areas.

[0106] The use of at least one of the heterocyclic substituted aromatic compounds or the herbicide composition in controlling weeds, preferably, the use of the heterocyclic substituted aromatic compounds in controlling weeds in useful crops, said useful crops being transgenic crops or crops treated with genome editing technology.

[0107] For many economically important monocotyledonous and dicotyledonous pests, the compounds of Formula I of this invention exhibit outstanding herbicidal activity. The active substances of this invention are also effective against perennial weeds that grow from rhizomes, stems, or other perennial organs and are difficult to control. In this regard, it is generally not important whether the substance is used before sowing, before germination, or after germination. Representative examples of monocotyledonous and dicotyledonous weed populations that can be controlled by the compounds of this invention are specifically mentioned, without limiting the specific species. Examples of weed species to which the active substances are effective include monocotyledons: annuals of *Oat*, *Rye*, *Grass*, *Alopecurus*, *Fararis*, *Barnyardgrass*, *Digitaria*, *Setaria*, and *Sedge*, and perennials of *Agrostis*, *Bermudagrass*, *Imperata*, and *Sorghum*, as well as perennials of *Sedge*.

[0108] Regarding dicotyledonous weed species, its effects can be extended to annual species such as *Galium aparine*, *Viola*, *Veronica*, *Sesamum indicum*, *Stellaria*, *Amaranthus*, *Sinapis*, *Ipomoea*, *Heliotropium*, *Chaenomeles*, and *Abutilon*, and perennial weeds such as *Convolvulus*, *Thistle*, *Rumex*, and *Artemisia*. The active substances of this invention effectively control harmful plants such as barnyard grass, *Sagittaria*, *Alisma*, *Eupatorium*, *Sedum*, and *Sedge* under the undetermined condition of rice sowing. If the compounds of this invention are applied to the soil surface before germination, weed seedlings can be completely prevented before they emerge, or growth can be stopped when the weeds develop cotyledons, eventually leading to their complete death after three to four weeks. The compounds of this invention exhibit particularly excellent activity against the following plants: *Apira*, *Sesamum indicum*, *Polygonum cuspidatum*, *Stellaria*, *Veronica ivy*, *Veronica arabiculata*, *Viola tricolor* and *Amaranthus*, *Galium aparine*, and *Kochia scoparia*.

[0109] While the compounds of this invention exhibit excellent herbicidal activity against both monocot and dicot weeds, they cause little to no damage to important economic crops such as wheat, barley, rye, rice, corn, sugar beets, cotton, and soybeans. They are particularly compatible with cereal crops, such as wheat, barley, and corn, especially wheat. Therefore, the compounds of this invention are highly suitable for the selective control of unwanted plants in agricultural or ornamental crops.

[0110] Due to their herbicidal properties, these active substances can be used to control harmful plants in known or future genetically engineered plant cultivation. Transgenic plants typically possess superior traits, such as resistance to specific insecticides, particularly specific herbicides, and resistance to plant diseases or pathogenic microorganisms, such as specific insects or fungi, bacteria, or viruses. Other specific traits relate to conditions such as quantity, quality, storage stability, composition, and special components of the product. Thus, it is known that transgenic plant products have increased starch content or improved starch quality or different fatty acid compositions.

[0111] The compounds of Formula I of the present invention, or salts thereof, are preferably used in the cultivation of economically important genetically modified crops and ornamental plants, such as cereals, including wheat, barley, rye, oats, millet, rice, cassava, and corn, or in the cultivation of sugar beets, cotton, soybeans, rapeseed, potatoes, tomatoes, peas, and other vegetable plants. The compounds of Formula I are preferably used as herbicides for the cultivation of useful plants that are resistant or have been genetically engineered to be resistant to the toxic effects of the herbicides.

[0112] Traditional methods for breeding plants with improved morphology compared to known plants include, for example, conventional mating methods and mutant breeding. In other words, new plants with improved traits can be obtained using genetic engineering methods (see, for example, EP-0221044 A, EP-0131624 A). Several methods have been described, for example:

[0113] - To improve starch synthesis in plants, genetic engineering is used to modify crop plants (e.g., WO 92 / 11376, WO92 / 14827, WO 91 / 19806).

[0114] - Transgenic crop plants resistant to specific herbicides, such as glufosinate-methyl (e.g., EP-0242236A, EP-0242246 A), glyphosate-based herbicides (WO 92 / 00377), or sulfonylurea herbicides (EP-0257993A, US-5013659 A).

[0115] - For example, genetically modified cotton plants can produce Bt toxins, which can defend against certain pests (EP-0142924 A, EP-0193259 A).

[0116] - A genetically modified crop plant with improved fatty acid composition (WO91 / 13972).

[0117] Many molecular biotechnologies for preparing transgenic plants with improved traits are known (see, for example, Sambrook et al., 1989, Molecular Amplification, Laboratory Manual, 2nd ed., Cold Spring Harbor Laboratory, Cold Spring Harbor, New York; or Winnacker, “Gene und Klone”, VCH Weinheim, 2nd ed., 1996; or Christou, “Trends in Plant Science” 1 (1996) 423-431). To achieve the manipulation of genetic engineering, nucleic acid molecules may be introduced into plasmids, resulting in mutations or sequence alterations through recombination of DNA sequences. Using standard methods described above, substrates may be exchanged, parts of the sequence may be removed, or natural or synthetic sequences may be added. To link DNA fragments together, it is possible to attach conjugates or linkers to the fragments.

[0118] Plant cells containing reduced-activity gene products can be prepared by methods such as expressing at least one appropriate antisense RNA or sense RNA to achieve co-inhibition, or by expressing at least one appropriately constructed ribozyme that specifically cleaves the transcript of the aforementioned gene product.

[0119] For this purpose, it is possible to use a DNA molecule containing the entire coding sequence of the gene product, including any possible flanking sequences, or a DNA molecule containing only a portion of the coding sequence, which must be long enough to achieve an antisense effect in the cell. Alternatively, a sequence that is highly homologous to but not identical to the coding sequence of the gene product can also be used.

[0120] When nucleic acid molecules are expressed in plants, the synthesized proteins can be localized in any desired plant cell compartment. However, to localize in a specific compartment, it is possible, for example, to link the coding region to a DNA sequence to ensure localization at a specific location. These sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992) 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al. Plant J. 1 (1991), 95-106).

[0121] Using known techniques, transgenic plant cells can be recombined into the entire plant. Transgenic plants can be any desired plant variety, i.e., monocots and dicots. In this way, it is possible to obtain transgenic plants with improved traits by overexpressing, inhibiting or suppressing homologous (=natural) genes or gene sequences, or by expressing heterologous (=external) genes or gene sequences.

[0122] When the active substances of this invention are used on genetically modified crops, in addition to the inhibitory effect on harmful plants observed in other crops, they often exhibit specific effects on the corresponding genetically modified crops. For example, they can improve or expand the range of weed control, improve the application rate, preferably combine the herbicide resistance of the genetically modified crop with the performance of the herbicide, and affect the growth and yield of the genetically modified crop. Therefore, this invention also provides the use of the compounds as herbicides to control harmful plants in genetically modified crop plants.

[0123] Furthermore, the compounds of this invention can significantly regulate crop growth. By modulating plant metabolism, these compounds can be used to directionally control plant components and promote harvesting, for example, by causing plant drying and dwarfing. They are also suitable for regulating and inhibiting unwanted plant growth without disrupting crop growth. Inhibiting plant growth plays a crucial role in many monocot and dicot crops because it can reduce or completely prevent lodging.

[0124] The compounds of the present invention can be applied using common formulations, including wettable powders, concentrated emulsions, sprayable solutions, powders, or granules. Thus, the present invention also provides herbicide compositions comprising compounds of formula I. Compounds of formula I can be formulated in various ways depending on typical biological and / or chemical physical parameters. Examples of suitable formulation choices include: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, concentrated emulsions (EC), emulsions such as oil dispersed in water and water dispersed in oil (EW), sprayable solutions, suspension concentrates (SC), dispersible oil suspensions (OD), suspensions diluted with oil or water, solutions miscible with oil, powders (DP), capsule suspensions (CS), seeddressing compositions, granules for broadcasting and soil application, spray granules, coating granules and absorbent granules, water-dispersible granules (WG), water-soluble granules (SG), ULV (ultra-low volume) formulations, microcapsules, and wax products. These individual formulation types are known and described in the following literature, for example, Winnacker-Küchler, “Chemische Techonologie” [Chemical Processes], Vol. 7, C. Hauser Verlag Munich, 4th ed. 1986; Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, NY, 1973; K. Martens, “Spray Drying” Handbook, 3rd ed. 1979, G. Goodwin Ltd. London.

[0125] Necessary formulation adjuvants, such as inert substances, surfactants, solvents, and other additives, are also known and described in the following documents, for example, Watkins's "Handbook of Powder Diluents, Insecticides, and Carriers," 2nd ed., Darland, Caldwell, NJ; Hv01phen's "Introduction to Clay Colloid Chemistry," 2nd ed., J. Wiley and Sons, NY; C. Marsden's "Guide to Solvents," 2nd ed., Interscience, NY 1963; McCutcheon's "Annual Report on Detergents and Emulsifiers," MC Publishing, Ridgewood, NJ; Sisley and Wood, "Encyclopedia of Surfactants," Chemical Publishing, NY 1964; Schönfeldt's "Grenzflächenaktive Äthylenoxidaddkte" [Ethylene oxide adduct surfactants], Wiss. Verlagagesell. Stuttgart 1976; Winnacker-Küchler's "Chemische "Technologie" [Chemical Processes], Vol. 7, C. Hauser Verlag Munich, 4th edition, 1986.

[0126] Wettable powders are uniformly dispersible in water and, in addition to the active ingredient, include diluents or inert substances, ionic and nonionic surfactants (wetting agents, dispersants), such as polyethoxyalkylphenols, polyethoxy fatty alcohols, polyoxyethyl aliphatic amines, fatty alcohol polyethylene glycol ether sulfates, alkyl sulfonates, alkyl phenyl sulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate, or sodium oleoylmethyl taurate. To prepare wettable powders, the active ingredient of the herbicide is finely ground, for example using common equipment such as hammer mills, fan mills, and jet mills, while adjuvants are mixed in simultaneously or sequentially.

[0127] Concentrated emulsions are prepared by dissolving active ingredients in an organic solvent, such as butanol, cyclohexanone, dimethylformamide, xylene, or a mixture of higher-boiling aromatic compounds or hydrocarbons, and then adding one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers that can be used include, for example, calcium alkylaryl sulfonate of calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyethylene glycol esters, alkyl aromatic polyethylene glycol ethers, fatty alcohol polyethylene glycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters, or polyethylene oxide sorbitan esters such as polyethylene oxide sorbitan fatty acid esters.

[0128] The active substance and finely ground solid material are ground to obtain a powder. The solid material may be talc, natural clay such as kaolin, bentonite, and pyrophyllite, or diatomaceous earth. A water- or oil-based suspension may be prepared, for example, by wet grinding using a commercially available glass bead mill, with or without the addition of a surfactant of the other formulation type mentioned above.

[0129] Emulsions, such as oil-in-water (EW) emulsions, can be prepared using an aqueous organic solvent, a stirrer, a colloid mill, and / or a static mixer, and if necessary, by adding a surfactant of another formulation type as described above.

[0130] Granules can be prepared by spraying the active material onto an adsorbent and granulating it using an inert material, or by concentrating the active material onto the surface of a carrier such as sand or kaolinite and granulating it using a binder such as polyvinyl alcohol, sodium polyacrylate, or mineral oil. Suitable active materials can be granulated using methods for preparing fertilizer granules, and fertilizers can be mixed in if necessary. Aqueous suspension granules can be prepared using conventional methods such as spray-drying, fluidized bed granulation, disc granulation, mixing using a high-speed mixer, and extrusion without solid inert material.

[0131] For methods of preparing granules using milling discs, fluidized beds, extruders, and spraying, see the following processes, for example, “Spray Drying Handbook,” 3rd edition, 1979, G. Goodwin Ltd, London; J.E. Browning, “Agglomeration,” Chemicals and Engineering, 1967, 147ff; and “Perry’s Chemical Engineer’s Handbook,” 5th edition, McGraw-Hill, New York, 1973, 8–57. For information on formulations of crop protection products, see, for example, GC. Klingman, “Weed Control as a Science,” John Wiley and Sons, New York, 1961, 81–96; and JD. Freyer and SA. Evans, “Weed Control Handbook,” 5th edition, Blackwell Scientific Rublications, Oxford University Press, 1968, 101–103.

[0132] Agricultural chemical formulations typically contain 0.1% to 99%, particularly 0.1% to 95%, of active ingredient Formula I by weight. The concentration of active ingredient in wettable powders is, for example, from about 10% to 99% by weight, with the usual formulation components comprising the remainder to 100% by weight. The concentration of active ingredient in concentrated emulsions can be from about 1% to 90% by weight, preferably 5% to 80%. Powder formulations contain 1% to 30% active ingredient by weight, typically preferably 5% to 20% by weight; however, sprayable solutions contain about 0.05% to 80% by weight, preferably 2% to 50% by weight. The content of active ingredient in aqueous suspension granules depends primarily on whether the active ingredient is liquid or solid, and on the additives, fillers, etc., used during granulation. The content of active ingredient in aqueous suspension granules is, for example, between 1% and 95% by weight, preferably between 10% and 80% by weight.

[0133] The formulation of the active substance may also include thickeners, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, defoamers, evaporation inhibitors, and pH and viscosity adjusters that are commonly used in all cases.

[0134] Based on these formulations, they may also be mixed with other insecticidal active substances such as insecticides, acaricides, herbicides and fungicides, or with safeners, fertilizers and / or plant growth regulators. The mixing method may be pre-mixed or bottled.

[0135] Suitable active substances that can be mixed with the active substances of the present invention in compound formulations or tank-mixed formulations include, for example, known substances in the "World Encyclopedia of New Pesticide Varieties Technology", China Agricultural Science and Technology Press, 2010.9 and the literature cited herein. For example, the following herbicidal active substances can be mixed with mixtures of Formula I (Note: the name of the compound, either the common name according to the International Organization for Standardization (ISO) or the chemical name, with a code where appropriate): acetochlor, butachlor, metolachlor, isopropachlor, isopropachlor, succinyl-metolachlor, propachlor, chlorpyrifos, chlorpyrifos, naphthalenepropanoyl-methyl, R-L-naphthalenepropanoyl-methyl, propargyl, benzylthiamethoxam, bisbenzyl-methyl, pyrifluquinazon, chlorpyrifos, flubutyroxyfen, brobutyroxyfen, dimethomorph, high-efficiency dimethomorph, ethoxybenzyl-methyl, flubutyroxyfen, methoxyfenazon, pyrifluquinazon, isoxaflutole, high-efficiency methylparaben, high-efficiency methylparaben, dimethomorph ... Acrylamide, clethodim, butyrazoline, cyprochloraz, flusulfanilamide, heptanoylamide, isobutanilamide, propyzamide, terbutanilamide, methylparaben, metolachlor, methylcyclohexane, chlorpyrifos, propyzamide, pendimethalin, carbaryl, succinylmethrin, tricyclomethrin, butyrazoline, succinylmethrin, bensulfuron-methyl, naphthylmethrin, acetochlor, naphthylmethrin, thiamethoxam, pyrimethanil, bensulfuron-methyl, chlorpyrifos, chlorpyrifos, butyrazoline, butyrazoline, flupyrazole, atrazine, simazine, promethazine, cypermethrin, cypermethrin, atrazine, chlorpyrifos, isopropanil, flumethrin, terbutanil, terbutanil, triazine, cyprochlorazine, glyphosate, chlorpyrifos Phosphatidylcholine, Simazine, Ziziphus jujuba, Dichlorvos, Isoamyl acetate, Cyprodinil, Atrazine, Butyraz, Butyraz, Terbutaline, Methoxypropazine, Cypermethrin, Herbicides, Corozinil, Atrazine, Methoxypropazine, Glycyrrhizin, Cyanide, Indaziflam, Greensulfuron, Bensulfuron-methyl, Chlorpyrifos, Bensulfuron-methyl, Thisulfuron-methyl, Pyrimisulfuron-methyl, Methiosulfuron-methyl, Sodium formamide pyrimisulfuron, Ethersulfuron-methyl, Etherbensulfuron-methyl, Methoxysulfuron-methyl, Nicosulfuron-methyl, Acrylpyrimisulfuron, Ethoxypyrimisulfuron, Cyprosulfuron-methyl, Sulfadiazine, Tetraazolidinyl, Pyrimisulfuron, Monopyrimisulfuron, Monopyrimisulfuron, Fluazolidinyl, Flupyrimisulfuron, Flupyrimisulfuron, Epipyrimisulfuron, Azoxypyrimisulfuron, Flupyrimisulfuron Sulfuric acid, propanilsulfuron, trifluprosulfuron, sulfonylsulfuron, trifluralinsulfuron, flumethrin, trifluralin, flupyrsulfuron, methoxysulfuron, pyrimethanil, propyrisulfuron, pyrimethanil, trifluralin, flusulfanilamide, quizalofop-p-ethyl, ethoxysulfuron, glyphosate, bensulfuron, chlorfluazuron, methylfluazuron, trifluralin, methoxysulfuron, trifluralin, flufenoxuron, flufenoxuron, metolachlor, methylfluazuron, halosafen, chlormequat chloride, isoproturon, linuron, diuron, sapura, fluroxypyr, bensulfuron, methyl bensulfuron, bensulfuron-methylSulfothiazoline, isoxaflutole, terbutaline, clodinafop-methyl, chlorothalonil, methyl methyl methoxychloride, methyl methoxychloride, bromonazine, methoxychloride, chlorpyrifos, metribuzin, cyclorhizobium, fenitrothion, flusulfuron, glufosinate, thiamethoxam, thiamethoxam, chlorpyrifos, thiamethoxam ... am, BCPC, CPPC, Carbasulam, Butadiene, Herbicides, Metazan, Herbicides, Wild Abamectin, Herbicides, Barnyardgrass, Cypermethrin, Oat Abamectin, Dimethoate, Ethylmethoxam, Methiobencarb, 2,4-D Sodium, 2,4-D Isooctyl Ester, 2,4-D Sodium Salt, 2,4-D Dimethylamine Salt, 2,4-D Ethylthioester, 2,4-D Propionic Acid, High 2,4-D Propionic Acid, 2,4-D Butyric Acid, 2,4-D Propionic Acid, 2,4-D Propionic Acid, 2,4-D Propionic Acid, 2,4-D Propionic Acid, 2,4-D Propionic Acid, 2,4-D Propionic Acid, 2,4-D Propionic Acid, 2,4,5-D, 2,4,5-D Propionic Acid, 2,4,5- Thymol, MCPA, dicamba, sedge, cyhalothrin, trichlorobenzoic acid, aminodichlorobenzoic acid, methoxytrichlorobenzoic acid, quizalofop-p-ethyl, pyrfluthrin, quizalofop-p-ethyl, flupyrfluthrin, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, cyhal ... Phosphate, herbicides, phosmet, chlorpyrifos, methamidophos, chlorpyrifos, imazalil, imazalil ethionyl acid, imazalil quinolinic acid, methoxymethylene, methoxymethylene ammonium salt, imazalil, imazalil, clopyralid, clopyralid isooctyl ester, dichloropyridine acid, ammoniapyridine acid, trichloropyridine acid, flusulfanil, haloxyfop-R-methyl, trichloropyridine phenol, thiamethoxam, flupyridine, chlorpyrifos, flupyridine hydrazone, trichloropyridine butoxyethyl ester, cliodinate, clethodim, thiamethoxam, quizalofop-P-ethyl, cyclobenzanil, butenazol, oximetris, pyranazol, buthidazole, cyproconazole, cyclobenzanil, benzobenzanil, ametridione, amibuzin, bromobenzonitrileOctyl bromoxynil, octyl iodobenzonil, iodobenzonil, dichlorvos, diphenylacetonitrile, bispyribac-sodium, hydroxydichlorvos, Iodobonil, pyrimethanil, diflubenzuron, penoxsulam, sulfadiazine, chlorpyrifos-sulfuron-methyl, dichlorvos-sulfuron-methyl, pyrazosulfuron-methyl, fluroxypyr, bispyribac-sodium, pyrimimethoxam, cyclopyrimethanil, pyrimimethoxam, pyrimimethoxam, pyrimimethoxam, bispyribac-sulfuron-methyl, nicosulfuron-methyl, sulfadiazine, Tembotrione, Tefuryltrione, Bicyclopyrone, Ketodpiradox, isoxadiazine, isoxadiazine, Fenoxasulfone, Methiozolin, isopyram, pyrazosulfuron-methyl, pyrazosulfuron-methyl, pyrazosulfuron-methyl, fenvalerate, bensulfuron-methyl Pyrasulfotole, pyrazosulfuron, pyrazosulfuron, pyroxasulfone, pyrazosulfuron, flumetsulam, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, flumethrin, mesotrione, bencarbazone, pyrazosulfuron, flupropargyl, isoxydine, cyclopyrazosulfuron, terbupropion, flupropargyl, acetamiprid, flumezin, pentachlorophenol (sodium), dichlorophenol, terbupropion, terbupropion, pentonitrophenol, dinitrophenol, chlorophen, dichlorophen, dichlorophen, dichlorophen, dichlorophen, cyclopyrazosulfuron, flumethrin, methyl methazine, tetrazolium, flupyridazine Herbicides, chlorpyrifos, bromochlor, methamidophos, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, chlorpyrifos, bentazon, pyrazosulfuron, oxadiazon, cyprochloraz, isoxaflutole, cyclohexane, isopropyl methoxysulfuron, propargite, indicarboxysulfuron, sodium chlorate, cogon grass, trichloroacetic acid, monochloroacetic acid, hexachloroacetone, tetrafluoropropionic acid, forage grass, bromophenol oxime, triazole sulfonium, methomyl, furazolidone, furazolidone, ethoxysulfuron, pyrimethanil, chlorpyrifos, flurfluralin, barnyardgrass, acrolein, bensulfuron-methyl, metribuzin, oat ester, thiamethoxam, styracil, hydroxyzine, methoxybenzone, pyrimisulfuron-methyl, chlorpyrifos, trichloropropionic acid, Alorac, Diethamqua t, Etnipromid, Iprymidam, Ipfencarbazone, Thiencarbazone-methyl, Pyrimisulfan, Chlorflurazole, Tripropindan, Sulglycapin, methylsulfuron, Cambendichlor, Cyproterinic acid, Thiamethoxam, cypermethrin, cypermethrin, cypermethrin, cypermethrin, cypermethrin, cypermethrin, cypermethrin, pyrazole cypermethrin, furazolidone, oxadiazon, bis(oxazolyl)acrylic acid, dichloropropeneamine, fluorochloropyridinium ester, DOW fluorochloropyridinium ester, UBH-509, D489, LS 82-556, KPP-300, NC-324, NC-330, KH-218DPX-N8189, SC-0744, DOWCO535, DK-8910, V-53482, PP-600, MBH-001, KIH-9201, ET-751, KIH-6127 and KIH-2023. ,

[0136] When used, commercially available formulations are diluted in a common manner if necessary, such as with water for wettable powders, concentrated emulsions, suspensions, and granules suspended in water. Powders, granules for soil application, or solutions for broadcasting and spraying generally do not require further dilution with an inert substance before use. The required dosage of Formula I compound varies with external conditions, such as temperature, humidity, and the nature of the herbicide used. It can vary considerably, for example, from 0.001 to 1.0 kg ai / ha, or more active ingredient, but is preferably from 0.005 to 750 g ai / ha, particularly from 0.005 to 250 g ai / ha. Detailed Implementation

[0137] The following examples are for illustrative purposes only and should not be construed as limiting the invention in any way. The scope of protection of this invention is defined by the claims.

[0138] Given the economic efficiency and diversity of the compounds, we preferentially synthesized a number of compounds, some of which are listed in Table 1 below. Specific compound structures and corresponding compound information are shown in Tables 1-2. The compounds in Table 1 are only for better illustration of the present invention and do not limit the invention. Those skilled in the art should not interpret this as limiting the scope of the above-mentioned subject matter of the invention to the following compounds.

[0139] Table 1. Compound Structures

[0140]

[0141]

[0142] Table 2 Compounds 1HNMR

[0143] Serial Number <![CDATA[ 1 H NMR]]> 1 <![CDATA[ 1 H NMR (300 MHz, Chloroform-d) δ 8.78 (s, 1H), 7.79 (d, J = 7.5Hz, 1H), 7.31 (d, J = 9.0 Hz, 1H), 4.27 (q, J = 7.0 Hz, 2H), 4.00(d, J = 17.5 Hz, 1H), 3.40 (d, J = 17.5 Hz, 1H), 2.62 (s, 3H),1.72 (s, 3H), 1.32 (t, J = 7.0 Hz, 3H). <!-- 32 -->]]> 10 <![CDATA[ 1 H NMR (300 MHz, Chloroform-d) δ 8.85 (s, 1H), 8.07 (s, 1H), 7.72(d, J = 7.2 Hz, 1H), 7.52 (d, J = 8.7 Hz, 1H), 4.01 (d, J = 17.4Hz, 1H), 3.83 (q, J = 7.2 Hz, 2H), 3.43 (d, J = 17.4 Hz, 1H), 1.74(s, 3H), 1.26 (t, J = 7.2 Hz, 3H).]]> 12 <![CDATA[ 1 H NMR (300 MHz, DMSO-d6) δ 9.09 (s, 1H), 8.68 (s, 1H), 7.88 –7.81 (m, 2H), 4.18 (q, J = 6.9 Hz, 2H), 3.79 (d, J = 18.0 Hz, 1H),3.58 (d, J = 18.0 Hz, 1H), 2.33 – 2.23 (m, 1H), 1.21 (t, J = 6.9Hz, 3H), 0.91 – 0.85 (m, 6H).]]> 15 <![CDATA[ 1 H NMR (300 MHz, Chloroform-d) δ 8.85 (s, 1H), 8.07 (s, 1H), 7.56(d, J = 7.0 Hz, 1H), 7.36 (d, J = 9.0 Hz, 1H), 5.14-5.12 (m, 1H),4.18 (q, J = 7.0Hz, 2H), 3.60 -3.58(m, 1H), 1.39-1.30 (m, 4H),0.88-0.56 (m, 4H).]]> 43 <![CDATA[ 1 H NMR (300 MHz, DMSO-d6) δ 9.10 (m, 1H), 8.70 (s, 1H), 7.85 (d, J= 9.0 Hz, 1H), 7.82 (d, J = 7.0 Hz, 1H), 5.19 – 5.08 (m, 1H), 3.92– 3.82 (m, 1H), 3.52 – 3.45 (m, 1H), 1.85 – 1.59 (m, 8H), 1.56 (s,3H).]]> 44 <![CDATA[ 1 H NMR (300 MHz, Chloroform-d) δ 8.86 (s, 1H), 8.07 (s,1H), 7.83(d, J = 7.5 Hz, 1H), 7.32 (d, J = 9.0 Hz, 1H), 4.80 - 4.70 (m,1H), 4.60 - 4.52 (m, 1H), 4.53 – 4.47 (m, 1H), 4.45 – 4.36 (m,1H), 4.02 (d, J = 17.5 Hz, 1H), 3.44 (d, J = 17.5Hz, 1H), 1.75 (s,3H).]]> 45 <![CDATA[ 1 H NMR (300 MHz, Chloroform-d) δ 8.85 (s, 1H), 8.07 (s, 1H), 7.83(d, J = 7.5 Hz, 1H), 7.33 (d, J = 9.0 Hz, 1H), 4.62 - 4.50 (m,2H), 4.02 (d, J = 17.5 Hz, 1H), 3.50 (d, J = 17.5 Hz, 1H)), 1.78(s, 3H).]]> 49 <![CDATA[ 1 H NMR (300 MHz, CDCl3) δ 8.87 (s, 1H), 8.06 (s, 1H), 7.82 (d, J =7.0 Hz, 1H), 7.31 (d, J = 9.0 Hz, 1H), 5.36 – 5.31 (m, 2H), 4.04(d, J = 17.5 Hz, 1H), 3.49 – 3.46 (m, 3H), 3.42 (d, J = 17.5 Hz,1H), 1.74 (s, 3H).]]> 50 <![CDATA[ 1 H NMR (300 MHz, CDCl3) δ 8.86 (d, J = 0.7 Hz, 1H), 8.07 (d, J =1.9 Hz, 1H), 7.84 (d, J = 7.4 Hz, 1H), 7.33 (d, J = 9.1 Hz, 1H),5.27 (d, J = 1.8 Hz, 2H), 4.04 (d, J = 17.4 Hz, 1H), 3.43 (d, J =17.4 Hz, 1H), 2.26 (s, 3H), 1.75 (s, 4H).]]> 51 <![CDATA[ 1 H NMR (300 MHz, DMSO-d6) δ 9.10 (s, 1H), 8.70 (s, 1H), 7.87 (d, J= 7.5 Hz, 1H), 7.32 (d, J = 9.0 Hz, 1H), 5.58 - 5.52 (m, 1H), 3.99– 3.90 (m, 1H), 3.60 - 3.55 (m, 1H), 1.63 (s, 3H), 1.58 (d, J =7.0 Hz, 3H).]]> 65 <![CDATA[ 1 H NMR (300 MHz, Chloroform-d) δ 8.85 (s , 1H), 8.06 (s, 1H), 7.81(d, J = 7.5 Hz, 1H), 7.32 (d, J = 9.0 Hz, 1H), 4.11 (d, J = 17.5Hz, 1H), 3.45 (d, J = 17.5 Hz, 1H), 2.06 (d, J = 5.5 Hz, 6H), 1.80(s, 3H).]]> 67 <![CDATA[ 1 H NMR (300 MHz, Chloroform-d) δ 8.85 (s, 1H), 8.07 (s, 1H), 7.82(d, J = 7.2 Hz, 1H), 7.34 (d, J = 9.0 Hz, 1H), 4.14 (d, J = 17.4Hz, 1H), 3.50 (d, J = 17.4 Hz, 1H), 2.23 (s, 3H), 1.84 (s, 3H). <!-- 33 -->]]> 68 <![CDATA[ 1 H NMR (300 MHz, Chloroform-d) δ 8.85 (s, 1H), 8.07 (s, 1H), 7.82(d, J = 7.5 Hz, 1H), 7.33 (d, J = 9.0 Hz, 1H), 4.17 – 4.05 (m,3H), 3.47 (d, J = 17.4 Hz, 1H), 3.35 (s, 3H), 2.09 (s, 3H), 1.81(s, 3H).]]> 69 <![CDATA[ 1 H NMR (300 MHz, Chloroform-d) δ 8.85 (s, 1H), 8.06 (s, 1H), 7.81(d, J = 7.2 Hz, 1H), 7.32 (d, J = 9.0 Hz, 1H), 4.20 (q, J = 7.2Hz, 2H), 4.10 (d, J = 17.4 Hz, 1H), 3.44 (d, J = 17.4 Hz, 1H),2.07 (s, 3H), 1.79 (s, 3H), 1.32 (t, J = 7.2 Hz, 3H).]]> 70 <![CDATA[ 1 H NMR (300 MHz, Chloroform-d) δ 8.79 (s, 1H), 8.01 (s, 1H), 7.83-7.69 (m, 1H), 7.36 – 7.22 (m, 1H), 4.36 – 4.20 (m, 2H), 4.41-3.90(m, 1H), 3.53-3.33 (m, 1H), 2.25-2.01 (m, 3H), 1.82-1.64 (m, 3H),1.34-1.25 (m, 3H).]]> 71 <![CDATA[ 1 H NMR (300 MHz, Chloroform-d) δ 8.87 (s, 1H), 8.08 (s, 1H), 7.71(d, J = 7.2 Hz, 1H), 7.59 (d, J = 9.0 Hz, 1H), 7.46 – 7.30 (m,10H), 3.86 (d, J = 17.4 Hz, 1H), 3.34 (d, J = 17.4 Hz, 1H), 1.62(s, 3H).]]> 72 <![CDATA[ 1 H NMR (300 MHz, Chloroform-d) δ 8.85 (s, 1H), 8.34 (s, 1H), 8.06(s, 1H), 7.86-7.74 (m, 1H), 7.58 (d, J = 2.4 Hz, 1H), 7.37-7.24(m, 1H), 6.95 – 6.93 (m, 1H), 6.53 – 6.50 (m, 1H), 4.14 (d, J =17.4 Hz, 1H), 3.51 (d, J = 17.4 Hz, 1H), 1.81 (s, 3H).]]> 73 <![CDATA[ 1 H NMR (300 MHz, Chloroform-d) δ 8.86 (s, 1H), 8.34 (s, 1H), 8.06(s, 1H), 7.82 (d, J = 7.2 Hz, 1H), 7.31 (d, J = 9.0, 1H), 6.95 –6.83 (m, 2H), 4.12 (d, J = 17.4 Hz, 1H), 3.49 (d, J = 17.4 Hz,1H), 2.35 (s, 3H), 1.81 (s, 3H).]]> 74 <![CDATA[ 1 H NMR (300 MHz, Chloroform-d) δ 8.85 (s, 1H), 8. 06 (s, 1H), 7.82(d, J = 7.2 Hz, 1H), 7.32 (d, J = 9.0 Hz, 1H), 4.11 (d, J = 17.4Hz, 1H), 3.45 (d, J = 17.4 Hz, 1H), 2.64 – 2.55 (m, 4H), 1.84 –1.80 (m, 4H), 1.78 (s, 3H).]]> 76 <![CDATA[ 1 H NMR (300 MHz, DMSO-d6) δ 9.10 (s, 1H), 8.70 (s, 1H), 7.83 (s,1H), 7.80 (d, J = 3.0 Hz, 1H), 4.06-3.99 (m,2H), 3.37 (d, J = 17.7Hz, 1H), 3.21 (d, J = 17.7 Hz, 1H), 2.41 – 2.31 (m, 2H), 1.95 –1.90 (m, 2H), 1.36 (s, 3H), 1.14 (t, J = 9.0 Hz, 3H).]]> 78 <![CDATA[ 1 H NMR (300 MHz, CDCl3)δ 8.85 (s, 1H), 8.06 (s, 1H), 7.83 (d, J =7.5 Hz, 1H), 7.31 (d, J = 9.0 Hz, 1H), 3.86 (d, J = 17.5 Hz, 1H),3.44 (d, J = 17.5 Hz, 1H), 2.85 (dd, J = 7.5Hz, 2H), 1.71 (s, 3H),1.23 (d, J = 7.5 Hz, 3H).]]> 97 <![CDATA[ 1 H NMR (300 MHz, CDCl3) δ 8.85 (s, 1H), 8.06 (s, 1H), 7.83 (d, J =7.5 Hz, 1H), 7.31 (d, J = 9.0 Hz, 1H), 5.97 (s, 1H), 4.16 (d, J =18.0 Hz, 1H), 3.71 (d, J = 18.0 Hz, 1H), 2.55 (s, 3H), 2.22 (s,3H), 1.96 (s, 3H).]]> 102 <![CDATA[ 1 H NMR (300 MHz, Chloroform-d) δ 8.30 (d, J = 2.7 Hz, 1H), 7.77(d, J = 7.5 Hz, 1H), 7.33 (d, J = 2.7 Hz, 1H), 7.27 (d, J = 8.7Hz, 1H), 4.26 (q, J = 6.9 Hz, 2H), 3.99 (d, J = 17.7 Hz, 1H), 3.91(s, 3H), 3.39 (d, J = 17.7 Hz, 1H), 1.71 (s, 3H), 1.32 (t, J = 6.9Hz, 3H). <!-- 34 -->]]> 104 <![CDATA[ 1 H NMR (300 MHz, Chloroform-d) δ 8.68 (d, J = 2.1 Hz, 1H), 7.84(d, J = 2.1 Hz, 1H), 7.81 (d, J = 7.5, Hz, 1H), 7.29 (d, J = 9.3Hz, 1H), 5.53 (d, J = 1.8 Hz, 1H), 5.29 (d, J = 1.8 Hz, 1H), 5.26(s, 2H), 4.02 (d, J = 17.4 Hz, 1H), 3.42 (d, J = 17.4 Hz, 1H),2.26 (s, 3H), 2.19 (s, 3H), 1.74 (s, 3H).]]> 105 <![CDATA[ 1 H NMR (300 MHz, Chloroform-d) δ 8.86 (s, 1H), 8.07 (s, 1H), 7.85(d, J = 7.2 Hz, 1H), 7.34 (d, J = 9.0 Hz, 1H), 5.29 – 5.17 (m,1H), 4.39 (t, J = 6.9 Hz, 2H), 3.89 – 3.76 (m, 2H), 2.78 (t, J =6.9 Hz, 2H), 2.16 (s, 3H).]]> 111 <![CDATA[ 1 H NMR (300 MHz, DMSO-d6) δ 9.09 (s, 1H), 8.70 (s, 1H), 7.89-7.77(m, 2H), 4.20 – 4.13 (m, 1H), 2.07 – 2.06 (m, 3H), 2.01 – 2.00 (m,3H), 1.47 (s, 3H), 1.01 (d, J = 7.5 Hz, 3H).]]> 113 <![CDATA[ 1 H NMR (300 MHz, Chloroform-d) δ 8.67 (d, J = 2.1 Hz, 1H), 7.84(d, J = 2.1 Hz, 1H), 7.79 (d, J = 7.5 Hz, 1H), 7.29 (d, J = 9.3Hz, 1H), 5.52 (d, J = 1.8 Hz, 1H), 5.29 (d, J = 1.8 Hz, 1H), 4.10(d, J = 17.7 Hz, 1H), 3.44 (d, J = 17.7 Hz, 1H), 2.19-2.17 (t, J =2.4 Hz, 3H), 2.07 (s, 3H), 2.05 (s, 3H), 1.79 (s, 3H).]]> 127 <![CDATA[ 1 H NMR (300 MHz, Chloroform-d) δ 8.87 (s, 1H), 8.08 (s, 1H), 7.84(d, J = 7.2 Hz, 1H), 7.37 (d, J = 9.0 Hz, 1H), 4.34 (d, J = 18.3Hz, 1H), 4.01 (d, J = 18.3 Hz, 1H), 2.10 (d, J = 3.0 Hz, 6H).]]> 129 <![CDATA[ 1 H NMR (300 MHz, Chloroform-d) δ 8.79 (s, 1H), 8.00 (s, 1H), 7.70(d, J = 7.5 Hz, 1H), 7.26 (d, J = 9.0 Hz, 1H), 4.06 (d, J = 17.4Hz, 1H), 3.48 (d, J = 17.4 Hz, 1H), 2.01 (d, J = 3.0 Hz, 6H),1.31-1.29 (m, 1H), 0.77-0.69 (m, 2H), 0.59-0.48 (m, 2H).]]> 139 <![CDATA[ 1 H NMR (300 MHz, Chloroform-d) δ 8.88 (s, 1H), 8.10 (s, 1H), 7.72(d, J = 7.2 Hz, 1H), 7.61 (d, J = 9.5 Hz, 1H), 3.95 (d, J = 17.4Hz, 1H), 3.29 (d, J = 17.4 Hz, 1H), 2.12-2.03 (m, 6H), 1.80 (s,3H).]]> 140 <![CDATA[ 1 H NMR (300 MHz, Chloroform-d) δ 8.88 (s, 1H), 8.11 (s, 1H), 7.95(d, J = 6.6 Hz, 1H), 7.60 (d, J = 8.7 Hz, 1H), 4.15 (d, J = 17.4Hz, 1H), 3.51 (d, J = 17.4 Hz, 1H), 2.07 (d, J = 3.6 Hz, 6H), 1.83(s, 3H).]]> 141 <![CDATA[ 1 H NMR (300 MHz, Chloroform-d) δ 8.84 (s, 1H), 8. 06 (s, 1H), 7.80(d, J = 7.2 Hz, 1H), 7.32 (d, J = 9.0 Hz, 1H), 4.12 (d, J = 17.4Hz, 1H), 3.46 (d, J = 17.4 Hz, 1H), 2.44 – 2.38 (m, 1H), 1.82 (s,3H), 1.70 (s, 3H), 0.99 – 0.94 (m, 2H), 0.90 – 0.84 (m, 2H).]]>

[0144] Several methods for preparing the compounds of the present invention are described in detail in the following schemes and examples. The raw materials can be commercially available or prepared by methods known in the literature or as detailed in the description. Those skilled in the art will understand that other synthetic routes can also be used to synthesize the compounds of the present invention. Although specific raw materials and conditions in the synthetic routes have been described below, they can be easily replaced with other similar raw materials and conditions. Such variations or modifications to the preparation methods of the present invention, such as various isomers of the compounds, are all included within the scope of the present invention. Furthermore, the preparation methods described below can be further modified according to the disclosure of the present invention using conventional chemical methods well known to those skilled in the art. For example, protecting appropriate groups during the reaction process, etc.

[0145] The following method examples are provided to further illustrate the preparation methods of the present invention. The specific substances, types, and conditions used are intended to further explain the invention and are not intended to limit its reasonable scope. The reagents used in the synthetic compounds shown in the table below are either commercially available or can be easily prepared by those skilled in the art.

[0146] Examples of representative compounds are given below. The synthesis methods of other compounds are similar and will not be described in detail here.

[0147] 1. Synthesis of Compound 10

[0148] (1) Compound 10-1 (52.3 g, 0.21 mmol), ethylene glycol (25.6 g, 0.42 mol), and p-toluenesulfonic acid (3.4 g, 0.02 mol) were dissolved in toluene (500 ml) and reacted at 120 °C for 8 h. After the raw materials were consumed by liquid chromatography, the mixture was cooled and concentrated. Water was added, and the mixture was extracted three times with EA and washed three times with saturated brine. The organic phase was dried and concentrated to obtain the crude product. The crude product was mixed and passed through a column to obtain compound 10-2 (55.2 g, 0.18 mol) with a yield of 85%.

[0149]

[0150] (2) Compound 10⁻² (55.2 g, 0.18 mol) was dissolved in 500 mL of ethanol and 100 mL of water. Iron powder (50 g, 0.9 mol) and NH₄Cl (19 g, 0.36 mmol) were added. The mixture was heated to 60°C and reacted for 2 hours. The reaction was stopped by liquid chromatography. The reaction solution was cooled, filtered through a diatomaceous earth filter, and the mother liquor was concentrated to obtain a crude product. Ethyl acetate and water were added to wash the crude product. The mixture was separated, and the organic phase was concentrated to obtain a crude product. The crude product was stirred and passed through a column to obtain 10⁻³ (30 g, 0.11 mol), with a yield of 61%.

[0151]

[0152] (3) Compound 10-3 (10 g, 38 mmol) was dissolved in 200 mL of acetonitrile, and 10-4 (48 g, 1.90 mol) of bipinnatol borate ester was added. Then, tert-butyl nitrite (7.8 g, 76 mmol) was slowly added dropwise. The mixture was heated to 60 degrees and reacted for 12 h. The starting material disappeared as detected by liquid chromatography. The reaction solution was concentrated to obtain crude product. Water and ethyl acetate were added for extraction. The organic phase was dried and concentrated. The sample was stirred and passed through a column to obtain compound 10-5 (5.5 g, 14.7 mmol), with a yield of 39%.

[0153]

[0154] (4) Add 10-6 (0.4 g, 1.86 mmol), boronic ester 10-5 (1.04 g, 2.80 mmol) and potassium carbonate (0.78 g, 5.6 mmol) to a clean flask, then add 20 ml of 1,4-dioxane and 2 ml of water, and then evacuate under nitrogen protection 2-3 times. After evacuation, add 1,1'-bis(diphenylphosphine)ferrocene]palladium dichloromethane complex (44.74 mg, 54.79 μmol), evacuate again, and heat to 100 °C overnight. After the reaction is completed, the solvent is removed by vacuum distillation, washed with water, extracted with EA 2-3 times, and then washed with saturated saline 2-3 times. Add anhydrous sodium sulfate to the EA phase to dry it, add silica gel to mix the sample and pass it through a column for normal phase purification to obtain 10-7 (600 mg, 1.42 mmol).

[0155]

[0156] (5) Add 10-7 (0.6 g, 1.42 mmol) and hydroxylamine hydrochloride (0.48 g, 7.1 mmol) to a clean flask, add a mixed solvent of ethanol and water (10 ml: 2 ml), stir at 80 degrees Celsius for 3 hours, after the reaction is completed, directly mix the sample and purify in the forward direction to obtain 10-8 (540 mg, 1.36 mmol).

[0157]

[0158] (6) Add 10-8 (0.54 g, 1.36 mmol) and NCS (0.36 g, 2.72 mmol) to a clean flask, add 10 ml of DMF to dissolve, stir at 40 degrees Celsius for 3 hours, after the reaction is completed, add water to wash and then add EA to extract (extract 3 times with appropriate amount of EA), then wash the EA phase twice with appropriate amount of saturated saline, and evaporate to dryness to obtain white solid 10-9 (580 mg, 1.35 mmol).

[0159]

[0160] (7) Dissolve 10⁻⁹ (0.8 g, 0.69 mmol) and triethylamine (0.14 g, 1.38 mmol) in DCM, and add 10⁻¹⁰ (0.2 g, 0.46 mmol) of dichloromethane solution dropwise under ice bath conditions. After the addition is complete, remove the ice bath and incubate at room temperature overnight. After the intermediate-controlled reaction is complete, mix the sample directly and purify it in the forward direction to obtain compound 10 (70 mg, 0.14 mmol).

[0161]

[0162] 2. Synthesis of Compound 104

[0163] (1) In a 100 mL single-necked flask, add 104-1 (2 g, 10.62 mmol, 1.0 eq), 16 mL of 1,4-dioxane and 4 mL of water, cesium fluoride (3.23 g, 21.23 mmol, 2.0 eq), 104-2 (2.99 g, 15.92 mmol, 1.5 eq), and a catalytic amount of Pd(dppf)Cl2 (0.087 g, 0.096 mmol, 0.01 eq). After the additions are complete, purge the mixture with argon gas three times. The reaction solution is stirred overnight at 100 °C. LCMS analysis shows that the reaction of the starting materials is basically complete, and a major new peak is formed. Most of the solvent was removed by rotary evaporation of the reaction solution. 100 mL of water and ethyl acetate (100 mL * 3) were added for extraction. The organic phase was washed with saturated brine (100 mL * 3). After concentration, the organic phase was mixed and passed through a column to obtain 104-3 (2.5 g, 80% yield, pale yellow solid).

[0164]

[0165] (2) In a 100 mL single-necked flask, 104-3 (2.5 g, 8.44 mmol, 1.0 eq), AIBN (0.45 g, 2.72 mmol, 0.2 eq), NBS (2.25 g, 12.66 mmol, 1.5 eq), and 30 mL of acetonitrile were added sequentially. The mixture was then purged with argon three times, and the reaction solution was stirred overnight at 80 °C. LCMS analysis showed that the reaction was basically complete, with one major new peak. Most of the solvent in the reaction solution was evaporated by rotary evaporation, and 20 mL of water and ethyl acetate (50 mL * 3) were added for extraction. The organic phase was washed with saturated brine (20 mL * 3), and the organic phase was concentrated to obtain crude 104-4 (2.3 g, crude product, yellow solid). The crude product was directly added to the next step.

[0166]

[0167] (3) In a 100 mL single-necked flask, 104-4 (2.3 g, 6.13 mmol, 1.0 eq), N-methylmorpholine oxide (1.44 g, 12.23 mmol, 2 eq), and 30 mL of acetonitrile were added sequentially. The reaction solution was stirred overnight at room temperature. LCMS analysis showed that the reaction of the starting materials was basically complete, and a major new peak was formed. Most of the solvent in the reaction solution was evaporated by rotary evaporation, and 20 mL of water and ethyl acetate (50 mL * 3) were added for extraction. The organic phase was washed with saturated brine (20 mL * 3), and the organic phase was concentrated to obtain crude 104-5 (1.5 g, crude product, yellow solid). The crude product was directly added to the next step.

[0168]

[0169] (4) In a 100 mL single-necked flask, 104-5 (1.5 g, 4.84 mmol, 1.0 eq), hydroxylamine hydrochloride (0.34 g, 4.84 mmol, 1 eq), and 25 mL of ethanol were added sequentially. The reaction solution was stirred at room temperature for three hours. LCMS analysis showed that the reaction of the starting materials was basically complete, and a major new peak was formed. The solvent was removed by rotary evaporation of the reaction solution, and 20 mL of water and ethyl acetate (50 mL * 3) were added for extraction. The organic phase was washed with saturated brine (20 mL * 3), and the organic phase was concentrated to obtain crude product 104-6 (1.2 g, crude product, pale yellow solid). The crude product was directly added to the next step.

[0170]

[0171] (5) In a 100 mL single-necked flask, 104-6 (1.2 g, 3.69 mmol, 1.0 eq), NCS (0.52 g, 3.87 mmol, 1.05 eq), and 20 mL DMF were added sequentially. The reaction mixture was stirred at room temperature for three hours. LCMS analysis showed that the reaction of the starting materials was basically complete, with a major new peak formed. 100 mL of water and ethyl acetate (100 mL * 3) were added for extraction. The organic phase was washed with saturated brine (20 mL * 3). After concentration, crude 104-7 (0.9 g, crude product, yellow solid) was obtained and directly added to the next step.

[0172]

[0173] (6) At 25°C, ethyl methacrylate (0.75 g, 7.51 mmol, 3 eq), triethylamine (0.25 g, 2.5 mmol, 1 eq), and 15 mL of dichloromethane were added sequentially to a 100 mL single-necked flask. A dichloromethane solution of compound 104-7 (0.9 g, 2.5 mmol, 1 eq) was added dropwise, and the mixture was stirred at room temperature for 5 hours. LCMS analysis showed that the reaction of the starting material was basically complete, with a major new peak formed. Water (100 mL * 3) was added for extraction, and the organic phase was washed with saturated brine (20 mL * 3). After concentration, crude product 104-8 (0.7 g, crude product, yellow oily substance) was obtained. The crude product was directly added to the next step.

[0174]

[0175] (7) At 25°C, compound 104-8 (0.8 g, 1.89 mmol, 1 eq), lithium hydroxide (0.14 g, 5.7 mmol, 3 eq), 15 mL THF and 5 mL water were added sequentially to a 100 mL single-necked flask. The mixture was stirred at room temperature for 5 hours. LCMS analysis showed that the reaction of the starting material was basically complete, with a major new peak formed. The pH was adjusted to weakly acidic, and 100 mL of water and ethyl acetate (100 mL * 3) were added for extraction. The organic phase was washed with saturated brine (20 mL * 3), and the organic phase was concentrated to obtain crude product 104-9 (0.7 g, crude product, yellow oily substance). The crude product was directly added to the next step.

[0176]

[0177] (8) In a 100 mL single-necked flask, 104-9 (0.1 g, 0.24 mmol, 1.0 eq), chloromethyl methyl sulfide (0.047 g, 0.49 mmol, 2 eq), anhydrous potassium carbonate (0.1 g, 0.74 mmol, 3.0 eq), and 10 mL DMF were added sequentially, and the mixture was reacted at 45 °C for 3 hours. LCMS analysis showed that the reaction of the starting material was basically complete, with a major new peak formed. Extraction was performed by adding 20 mL of water and ethyl acetate (20 mL * 3). The organic phase was washed with saturated brine (20 mL * 3), concentrated, stirred, and passed through a column to obtain compound 104 (0.05 g, 44% yield, colorless oil).

[0178]

[0179] Bioactivity evaluation:

[0180] The activity level standards for plant damage (i.e., growth control rate) are as follows:

[0181] Level 10: Complete death;

[0182] Level 9: Growth control rate is greater than or equal to 90% and less than 100%;

[0183] Level 8: Growth control rate is greater than or equal to 80% and less than 90%;

[0184] Level 7: Growth control rate is greater than or equal to 70% and less than 80%;

[0185] Level 6: Growth control rate is greater than or equal to 60% and less than 70%;

[0186] Level 5: Growth control rate is greater than or equal to 50% and less than 60%;

[0187] Level 4: Growth control rate greater than or equal to 40% and less than 50%;

[0188] Level 3: Growth control rate greater than or equal to 30% and less than 40%;

[0189] Level 2: Growth control rate greater than or equal to 20% and less than 30%;

[0190] Level 1: Growth control rate less than 20%;

[0191] Level 0: No effect.

[0192] The above growth control rates are fresh weight control rates.

[0193] Post-emergence testing experiment:

[0194] Seeds of monocotyledonous and dicotyledonous weeds (such as shepherd's purse, velvetleaf, cleavers, chickweed, wild oats, watercress, wild oats, Japanese wild oats, goosegrass, purslane, hard grass, fleabane, candle grass, speedwell, wild oats, jointed goatgrass, wild oats, amaranth, lambsquarters, dayflower, sow thistle, field bindweed, sow thistle, black nightshade, iron amaranth, crabgrass, barnyard grass, green foxtail grass, golden foxtail grass, goosegrass, duckweed, arrowhead, firefly sedge, nutgrass, sedge, sedge, purslane, burdock, purslane, cocklebur, morning glory, white wine grass, etc.) and the main Crop seeds (wheat, corn, rice, soybean, cotton, rapeseed, millet, sorghum, potato, sesame, castor bean, etc.) were placed in plastic basins filled with soil, then covered with 0.5-2 cm of soil and allowed to grow in a good greenhouse environment. Two weeks after sowing, test plants were treated at the 2-3 leaf stage. The tested compound of this invention was dissolved in acetone, then Tween 80 was added, and methyl oleate emulsifiable concentrate at 1.5 L / ha was used as a synergist. The solution was diluted with water to a certain concentration and sprayed onto the plants using a spray tower. After three weeks of cultivation in the greenhouse, the experimental effect on weeds was statistically analyzed. The compound dosages used were 500, 250, 125, 60, 15, and 7.5 g ai / ha, with three replicates, and the average value was taken. Representative data are listed in Table 3.

[0195] Table 3 Results of post-emergence weed test

[0196] Serial Number barnyard grass Amaranth Veronica Abutilon Ma Tang Green foxtail grass Dosage (g ai / ha) 1 10 10 10 10 10 10 60 10 10 10 10 10 10 10 60 12 10 10 10 10 10 10 60 15 10 10 10 10 10 10 15 43 10 10 10 10 10 10 15 44 10 10 10 10 10 10 15 45 10 10 10 10 10 10 60 49 10 10 10 10 10 10 15 50 10 10 10 10 10 10 15 51 10 10 10 10 10 10 15 65 10 10 10 10 10 10 15 67 10 10 10 10 10 10 60 68 10 10 10 10 10 10 60 69 10 10 10 10 10 10 60 70 10 10 10 10 10 10 60 71 10 10 10 10 10 10 60 72 10 10 10 10 10 10 60 73 10 10 10 10 10 10 60 74 10 10 10 10 10 10 60 76 10 10 10 10 10 10 15 78 10 10 10 10 10 10 15 97 10 10 10 10 10 10 15 102 10 10 10 10 10 10 60 104 10 10 10 10 10 10 60 105 10 10 10 10 10 10 60 111 10 10 10 10 10 10 60 113 10 10 10 10 10 10 60 127 10 10 10 10 10 10 60 129 10 10 10 10 10 10 60 139 10 10 10 10 10 10 60 140 10 10 10 10 10 10 60 141 10 10 10 10 10 10 60

[0197] Pre-seeding test experiment:

[0198] Seeds of monocotyledonous and dicotyledonous weeds, as well as seeds of major crops (wheat, corn, rice, soybean, cotton, rapeseed, millet, and sorghum), were placed in plastic basins filled with soil and covered with 0.5-2 cm of soil. The tested compounds of this invention were dissolved in acetone, then Tween 80 was added, and the solution was diluted with water to a specific concentration. The solutions were sprayed immediately after sowing. After 4 weeks of cultivation in a greenhouse following application, the experimental results were observed. It was found that most of the herbicides of this invention showed excellent efficacy at a dosage of 250 g ai / ha, especially against barnyard grass, crabgrass, and velvetleaf, and many compounds exhibited good selectivity for corn, wheat, rice, and soybeans.

[0199] Meanwhile, through testing on major weeds in wheat and rice fields, we found that the compounds described in this invention generally have good weed control efficacy. In particular, we noted that they have extremely high activity against broadleaf weeds and sedges resistant to ALS inhibitors, such as arrowhead, fireweed, sedge, shepherd's purse, shepherd's purse, cleavers, nutgrass, and nutgrass, and have very good commercial value.

[0200] Furthermore, numerous tests have revealed that the compounds and their compositions described in this invention exhibit excellent selectivity against many grassy lawns, including Zoysia japonica, Bermuda grass, tall fescue, Kentucky bluegrass, ryegrass, and seashore paspalum, effectively controlling many key grassy weeds as well as broadleaf weeds. Tests on sugarcane, soybeans, cotton, sunflowers, potatoes, fruit trees, and vegetables under different application methods also demonstrated excellent selectivity and commercial value.

Claims

1. A heterocyclic substituted aromatic compound, as shown in general formula I: ， in, Y represents halogen, halogenated C1-C8 alkyl, or cyano; Z represents halogen; M1 represents CR5; M2 represents N(O) m ; Q represents CX3X4; m represents 0; R1, R2, R3, R4, and R5 independently represent hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, or -OR, respectively. 11 ,in, The "C1-C8 alkyl" is either unsubstituted or halogenated; X1 represents C1-C8 alkyl or C3-C8 cycloalkyl, and is not methyl or ethyl; X2 represents C1-C8 alkyl or Wherein, the "C1-C8 alkyl" is replaced by a group selected from "-(CO)OR"; X3 and X4 represent hydrogen or C1-C8 alkyl groups, respectively. "R" represents C1-C8 alkyl; W1 represents O; W2 represents OW3, SW3, or NW4W5; W3 independently represents C1-C8 alkyl, C3-C8 cycloalkyl, or Wherein, the "C1-C8 alkyl" is unsubstituted or selected from halogen, cyano, nitro, or At least one group in it is replaced; NW4W5 represents It is either unsubstituted or substituted with groups selected from C1-C8 alkyl groups; X 11 Each can independently represent a C1-C8 alkyl group; X 13 X 14 Each of these independently represents hydrogen, C1-C8 alkoxy, C1-C8 alkoxy-C1-C8 alkyl, C1-C8 alkoxy carbonyl, C1-C8 alkyl, C3-C8 cycloalkyl, phenyl, or , or the CX group 13 X 14 Together they form a 5-membered carbon ring, wherein the "C1-C8 alkyl" is unsubstituted or halogenated. or Each is independently either unsubstituted or substituted with a group selected from C1-C8 alkyl groups; R 11 Represents C1-C8 alkyl groups.

2. The heterocyclic substituted aromatic compound according to claim 1, characterized in that, Y represents halogen, halogenated C1-C6 alkyl, or cyano.

3. The heterocyclic substituted aromatic compound according to claim 1, characterized in that, Y represents halogen.

4. A heterocyclic substituted aromatic compound according to claim 1, characterized in that, R1, R2, R3, R4, and R5 independently represent hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, or -OR, respectively. 11 Wherein, the "C1-C6 alkyl" is unsubstituted or halogenated.

5. A heterocyclic substituted aromatic compound according to claim 1, characterized in that, R1, R2, R3, R4, and R5 independently represent hydrogen, halogen, C1-C6 alkyl, or -OR, respectively. 11 Wherein, the "C1-C6 alkyl" is unsubstituted or halogenated.

6. A heterocyclic substituted aromatic compound according to claim 1, characterized in that, X1 represents C1-C6 alkyl or C3-C6 cycloalkyl, and is not methyl or ethyl; X2 represents C1-C6 alkyl or Wherein, the "C1-C6 alkyl" is replaced by a group selected from "-(CO)OR"; X3 and X4 represent hydrogen or C1-C6 alkyl groups, respectively. "R" represents C1-C6 alkyl groups independently.

7. A heterocyclic substituted aromatic compound according to claim 1, characterized in that, X1 represents C3-C6 cycloalkyl; X2 represents C1-C6 alkyl or Wherein, the "C1-C6 alkyl" is replaced by a group selected from "-(CO)OR"; X3 and X4 each independently represent hydrogen; "R" represents C1-C6 alkyl groups independently.

8. A heterocyclic substituted aromatic compound according to claim 1, characterized in that, W3 independently represents C1-C6 alkyl, C3-C6 cycloalkyl, or Wherein, the "C1-C6 alkyl" is unsubstituted or selected from halogens, cyano groups, or One, two, or three groups in it are replaced; NW4W5 represents It is either unsubstituted or substituted with groups selected from C1-C6 alkyl groups; X 11 Each can independently represent a C1-C6 alkyl group; X 13 X 14 Each of these independently represents hydrogen, C1-C6 alkoxy, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkoxy carbonyl, C1-C6 alkyl, C3-C6 cycloalkyl, phenyl, or , or the CX group 13 X 14 Together they form a 5-membered saturated carbon ring, wherein the "C1-C6 alkyl" groups are individually unsubstituted or halogenated. or Each is independently either unsubstituted or substituted with a group selected from C1-C6 alkyl groups.

9. A heterocyclic substituted aromatic compound according to claim 1, characterized in that, W3 independently represents C1-C6 alkyl, C3-C6 cycloalkyl, or Wherein, the "C1-C6 alkyl" is unsubstituted or selected from halogens, cyano groups, or One, two, or three groups in it are replaced; NW4W5 represents It is either unsubstituted or substituted with groups selected from C1-C6 alkyl groups; X 11 Each can independently represent a C1-C6 alkyl group; X 13 X 14 Each of these independently represents hydrogen, C1-C6 alkoxy, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkoxy carbonyl, C1-C6 alkyl, phenyl, or , or the CX group 13 X 14 Together they form a 5-membered saturated carbon ring, wherein the "C1-C6 alkyl" groups are individually unsubstituted or halogenated. or Each is independently either unsubstituted or substituted with a group selected from C1-C6 alkyl groups.

10. A heterocyclic substituted aromatic compound according to claim 9, characterized in that, X 13 X 14 Each of these independently represents hydrogen, C1-C6 alkoxy, C1-C6 alkoxy-C1-C3 alkyl, C1-C6 alkoxy-carbonyl, C1-C6 alkyl, phenyl, or , or the CX group 13 X 14 Together they form a 5-membered saturated carbon ring, wherein the "C1-C6 alkyl" groups are individually unsubstituted or halogenated. or Each is independently either unsubstituted or substituted with a group selected from C1-C6 alkyl groups.

11. A heterocyclic substituted aromatic compound according to claim 1, characterized in that, R 11 Represents C1-C6 alkyl groups.

12. A heterocyclic substituted aromatic compound, said compound being selected from any one of the following compounds: ， 。 13. A method for preparing a heterocyclic substituted aromatic compound as described in any one of claims 1-12, characterized in that, Includes the following steps: The compound represented by general formula II is prepared by reacting it with the compound represented by general formula III. The chemical reaction equation for a compound represented by general formula I is as follows: ， Wherein, Hal represents a halogen, and the substituents X1, X2, R1, R2, R3, R4, M1, M2, Q, Y, and Z are defined as described in any one of claims 1-12.

14. The method for preparing heterocyclic substituted aromatic compounds according to claim 13, characterized in that, The reaction is carried out in the presence of a base and a solvent.

15. The method for preparing heterocyclic substituted aromatic compounds according to claim 14, characterized in that, The base is selected from at least one of nitrogen-containing bases; the solvent is selected from at least one of aromatic hydrocarbons, tetrahydrofuran, N,N-dimethylformamide, N,N-dimethylacetamide, methanol, ethanol, acetonitrile, dichloroethane, dimethyl sulfoxide, 1,4-dioxane, dichloromethane, or ethyl acetate.

16. A herbicide composition, characterized in that, Includes at least one of the heterocyclic substituted aromatic compounds according to any one of claims 1-12, in an effective amount for herbicidal purposes.

17. The herbicide composition according to claim 16, characterized in that, It also includes pharmaceutical additives.

18. A method for controlling weeds, characterized in that, The herbicide composition comprising at least one of the heterocyclic-substituted aromatic compounds of any one of claims 1-12 or the herbicide composition of claim 16 or 17 is used on plants or in weedy areas.

19. Use of at least one of the heterocyclic substituted aromatic compounds according to any one of claims 1-12 or the herbicide composition according to claim 16 or 17 in the control of weeds.

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