A heterocyclic-substituted aromatic compound, a preparation method thereof, a herbicidal composition and application thereof

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 ; R1, R2, R3, R4 and R5 independently represent hydrogen, halogen, etc.; X1 and X2 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] The present application belongs to the technical field of pesticides, and particularly relates to a heterocycle-substituted aromatic compound, a preparation method, a herbicidal composition and application thereof. BACKGROUND

[0002] The control of weeds is a crucial step in the process of efficient agriculture, although there are various types of herbicides on the market, such as the use of substituted biaromatic benzene sulfonamide compounds as herbicides disclosed in patent WO2012059050A. However, the herbicidal performance of these known compounds on harmful plants and the selectivity on crops are not completely satisfactory. And due to the continuous expansion of the market, the resistance of weeds, the service life of drugs and the economy of drugs and other problems, and the increasing attention of people to the environment, scientists need to continuously research and develop new herbicides with high efficiency, safety, economy and different modes of action. SUMMARY

[0003] The present application provides a heterocycle-substituted aromatic compound, a preparation method, a herbicidal composition and application thereof. The compound has excellent herbicidal activity on gramineous weeds, broadleaf weeds and the like even at a low application rate, and has high selectivity on crops.

[0004] The technical solutions adopted by the present application are as follows:

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

[0006]

[0007] Among them,

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

[0009] Z represents hydrogen, halogen or hydroxyl;

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

[0011] R1, R2, R3, R4, R5 respectively independently represent hydrogen, halogen, hydroxyl, mercapto, formyl, hydroxyalkyl, nitro, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, -OR 11 , -SR 11 , -(SO)R 11 , -(SO2)R 11 , -(SO2)OR 11 , -O(SO2)R 11 , -N(R 122. Phenyl or benzyl, wherein,

[0012] 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;

[0013] X1 and X2 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”, respectively. -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,

[0014] 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.

[0015] 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 14The 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-.

[0016] 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;

[0017] 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-.

[0018] "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 -SR13 13 13 13 13 14 14 14 14 14 14

[0019] W1represents O, S or NW4;

[0020] W2represents OW3, SW3or NW4W5;

[0021] W3independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, 14 14 14 14 14 14

[0022] ​​​​​​​​​​​​​​​​​​​W4, W5 independently represent hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, wherein said "alkyl", "alkenyl" or "alkynyl" is independently unsubstituted or substituted with at least one member selected from the group consisting of halogen, cyano, nitro, cycloalkyl, trialkylsilyl, cycloalkenyl, heterocyclyl, aryl, wherein said "cycloalkyl", "cycloalkenyl", "heterocyclyl" or "aryl" is independently unsubstituted or substituted with at least one member selected from the group consisting of oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR 14 , -SR 14 , -(CO)OR 14 , -(SO2)R 14 , -N(R 14 )2 or -O-alkyl-(CO)OR 14 , or two adjacent carbon atoms in the ring form a fused ring with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with halogen;

[0023] or NW4W5 represents or unsubstituted or substituted heterocyclyl with 1 -nitrogen atom in the 1 -position;

[0024] X 11 independently represent hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl or arylalkyl, wherein said "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl" or "arylalkyl" is independently unsubstituted or substituted with at least one member selected from the group consisting of oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR 14 , -SR 14 , -(CO)OR 14 , -(SO2)R 14 , -N(R 14 )2 or -O-alkyl-(CO)OR 14 , or two adjacent carbon atoms in the ring form a fused ring with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with halogen;

[0025] X 12independently of each other represent alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl or arylalkyl, wherein said "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl" or "arylalkyl" are independently of each other unsubstituted or substituted by at least one radical selected from the group consisting of oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, halogenalkyl, halogenalkenyl, halogenalkynyl, halogencycloalkyl, cycloalkyl substituted by alkyl, -OR 14 , -SR 14 , -(CO)OR 14 , -(SO2)R 14 , -N(R 14 )2 or -O-alkyl-(CO)OR 14 , or form a fused ring with the two adjacent carbon atoms in the ring which are unsubstituted or substituted by halogen, -OCH2CH2- or -OCH2O-;

[0026] X 13 , X 14 independently of each other represent hydrogen, halogen, cyano, alkoxy, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, or the radicals CX 13 X 14 together form an unsubstituted or substituted ring system, or the radicals NX 13 X 14 together form an unsubstituted or substituted heterocyclyl with the 1 -position being nitrogen, wherein said "alkyl", "alkenyl" or "alkynyl" are independently of each other unsubstituted or substituted by halogen, said "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "aryl", "arylalkyl", "heterocyclyl" or "heterocyclylalkyl" are independently of each other unsubstituted or substituted by at least one radical selected from the group consisting of oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, halogenalkyl, halogenalkenyl, halogenalkynyl, halogencycloalkyl, cycloalkyl substituted by alkyl, -OR 14 , -SR 14 , -(CO)OR 14 , -(SO2)R 14 , -N(R 14 )2 or -O-alkyl-(CO)OR 14 , or form a fused ring with the two adjacent carbon atoms in the ring which are unsubstituted or substituted by halogen, -OCH2CH2- or -OCH2O-;

[0027] R 11Each 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.

[0028] 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;

[0029] 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.

[0030] 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.

[0031] m represents 0 or 1.

[0032] In one specific embodiment, Y represents halogen, halogenated C1-C8 alkyl, cyano, nitro, or amino.

[0033] In another specific embodiment, Y represents halogen, halogenated C1-C6 alkyl, cyano, nitro, or amino.

[0034] 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)R11 -(SO2)R 11 -(SO2)OR 11 -O(SO2)R 11 -N(R 12 )2, phenyl or benzyl, wherein,

[0035] said "Ci-C8alkyl", "C2-C8alkenyl", "C2-C8alkynyl", "C3-C8cycloalkyl", "C3-C8cycloalkyl Ci-C8alkyl", "C3-C8cycloalkenyl" or "C3-C8cycloalkenyl Ci-C8alkyl" are each independently unsubstituted or substituted with halogen, said "phenyl" or "benzyl" are each independently unsubstituted or substituted with at least one group selected from halogen, cyano, nitro, Ci-C8alkyl, halo-Ci-C8alkyl, Ci-C8alkyloxycarbonyl, Ci-C8alkylthio, Ci-C8alkylsulfonyl, Ci-C8alkoxy or halo-Ci-C8alkoxy.

[0036] In another particular embodiment, R1, R2, R3, R4, R5represent each independently hydrogen, halogen, hydroxy, mercapto, formyl, hydroxy-Ci-C6alkyl, nitro, cyano, Ci-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C3-C6cycloalkyl-Ci-C6alkyl, C3-C6cycloalkenyl, C3-C6cycloalkenyl-Ci-C6alkyl, -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,

[0037] said "Ci-C6alkyl", "C2-C6alkenyl", "C2-C6alkynyl", "C3-C6cycloalkyl", "C3-C6cycloalkyl-Ci-C6alkyl", "C3-C6cycloalkenyl" or "C3-C6cycloalkenyl-Ci-C6alkyl" are each independently unsubstituted or substituted with halogen, said "phenyl" or "benzyl" are each independently unsubstituted or substituted with 1, 2 or 3 groups selected from halogen, cyano, nitro, Ci-C6alkyl, halo-Ci-C6alkyl, Ci-C6alkyloxycarbonyl, Ci-C6alkylthio, Ci-C6alkylsulfonyl, Ci-C6alkoxy or halo-Ci-C6alkoxy.

[0038] In another embodiment, R1, R2, R3, R4, R5, independently of one another, represent hydrogen, halogen, hydroxyl, thiol, formyl, hydroxyC1-C6alkyl, nitro, cyano, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C3alkyl, C3-C6cycloalkenyl, C3-C6cycloalkenylC1-C3alkyl, -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,

[0039] said "C1-C6alkyl", "C2-C6alkenyl", "C2-C6alkynyl", "C3-C6cycloalkyl", "C3-C6cycloalkylC1-C3alkyl", "C3-C6cycloalkenyl" or "C3-C6cycloalkenylC1-C3alkyl" are each independently unsubstituted or substituted by halogen, said "phenyl" or "benzyl" are each independently unsubstituted or substituted by 1, 2 or 3 radicals selected from halogen, cyano, nitro, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxycarbonyl, C1-C6alkylthio, C1-C6alkylsulfonyl, C1-C6alkoxy or haloC1-C6alkoxy.

[0040] In one embodiment, X1, X2, independently of one another, represent hydrogen, halogen, nitro, cyano, thiocyano, hydroxyl, thiol, sulfonic acid, formyl, haloformyl, azido, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, C3-C8cycloalkylC1-C8alkyl, C3-C8cycloalkenyl, C3-C8cycloalkenylC1-C8alkyl, -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'=N-O-R", heterocyclyl, heterocyclylC1-C8alkyl, aryl, arylC1-C8alkyl, amino, aminoC1-C8alkyl, aminocarbonylC1-C8alkyl, aminocarbonyloxyC1-C8alkyl, aminothiocarbonyloxyC1-C8alkyl, aminosulfonyl or aminosulfonyloxyC1-C8alkyl, wherein,

[0041] said "C1-C8alkyl", "C2-C8alkenyl" or "C2-C8alkinyl" is independently unsubstituted or substituted by at least one group selected from halogen, cyano, hydroxy, mercapto, carboxy, -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-C8alkyl)-(CO)OH or -O-(C1-C8alkyl)-(CO)OR", respectively,

[0042] said "C3-C8cycloalkyl", "C3-C8cycloalkylC1-C8alkyl", "C3-C8cycloalkenyl", "C3-C8cycloalkenylC1-C8alkyl", "heterocyclyl", "heterocyclylC1-C8alkyl", "aryl" or "arylC1-C8alkyl" is independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8alkyl, C2-C8alkenyl, C2-C8alkinyl, C3-C8cycloalkyl, halogen-C1-C8alkyl, halogen-C2-C8alkenyl, halogen-C2-C8alkinyl, halogen-C3-C8cycloalkyl, C3-C8cycloalkyl substituted by C1-C8alkyl, -OR 14 14 14 14 14 14 , or adjacent two carbon atoms in the ring form a fused ring with -OCH2CH2- or -OCH2O- which are unsubstituted or substituted by halogen,

[0043] said "amino", "aminoC1-C8alkyl", "aminocarbonylC1-C8alkyl", "aminocarbonyloxyC1-C8alkyl", "aminothiocarbonyloxyC1-C8alkyl", "aminosulfonyl" or "aminosulfonyloxyC1-C8alkyl" is independently unsubstituted or substituted by at least one group selected from -R 11 11 11 11 11 11 11 11 12 12 ​​​​​​​​​​​​​​Substituted by one or two groups of )2;

[0044] 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)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-.

[0045] "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 13substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, halogen-C1-C8alkyl, halogen-C2-C8alkenyl, halogen-C2-C8alkynyl, halogen-C3-C8cycloalkyl, C3-C8cycloalkyl substituted by C1-C8alkyl, -OR 14 14 14 14 14 14 substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, halogen-C1-C8alkyl, halogen-C2-C8alkenyl, halogen-C2-C8alkynyl, halogen-C3-C8cycloalkyl, C3-C8cycloalkyl substituted by C1-C8alkyl, -OR

[0046] In another particular embodiment, X1, X2independently represent hydrogen, halogen, nitro, cyano, thiocyano, hydroxy, mercapto, sulfonic acid, formyl, halogenformyl, azido, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C3-C6cycloalkyl-C1-C6alkyl, C3-C6cycloalkenyl, C3-C6cycloalkenyl-C1-C6alkyl, -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'=N-O-R", heterocyclyl, heterocyclyl-C1-C6alkyl, aryl, aryl-C1-C6alkyl, amino, amino-C1-C6alkyl, aminocarbonyl-C1-C6alkyl, aminocarbonyloxy-C1-C6alkyl, aminothiocarbonyloxy-C1-C6alkyl, aminosulfonyl or aminosulfonyloxy-C1-C6alkyl, wherein,

[0047] ​​​​​​said "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is independently unsubstituted or substituted by 1, 2 or 3 radicals from the group consisting of halogen, cyano, hydroxy, mercapto, carboxy, -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", respectively,

[0048] said "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "heterocyclyl", "heterocyclyl C1-C6 alkyl", "aryl" or "aryl C1-C6 alkyl" is independently unsubstituted or substituted by 1, 2 or 3 radicals from the group consisting of oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogen-C1-C6 alkyl, halogen-C2-C6 alkenyl, halogen-C2-C6 alkynyl, halogen-C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted by 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 , respectively, or form a fused ring with the two adjacent carbon atoms in the ring, which are unsubstituted or substituted by halogen, with -OCH2CH2- or -OCH2O-, respectively,

[0049] said "amino", "amino C1-C6 alkyl", "aminocarbonyl C1-C6 alkyl", "aminocarbonyloxy C1-C6 alkyl", "aminothiocarbonyloxy C1-C6 alkyl", "aminosulfonyl" or "aminosulfonyloxy C1-C6 alkyl" is independently unsubstituted or substituted by 1, 2 or 3 radicals from the group consisting of -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 12Substituted by one or two groups of )2;

[0050] 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)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-.

[0051] "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 13substituted by 1, 2 or 3 groups independently selected from oxo, halogen, cyano, nitro, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, halogen-C1-C6alkyl, halogen-C2-C6alkenyl, halogen-C2-C6alkynyl, halogen-C3-C6cycloalkyl, C3-C6cycloalkyl substituted by C1-C6alkyl, -OR 14 , -SR 14 , -(CO)OR 14 , -(SO2)R 14 , -N(R 14 )2or -O-(C1-C6alkyl)-(CO)OR 14 , or by an oxo group, or by two oxo groups, or by two halogen atoms, or by two halogen atoms and one oxo group, or by one oxo group and one halogen atom, or by one oxo group and one cyano group, or by one oxo group and one nitro group, or by one oxo group and one -OR

[0052] In another particular embodiment, X1, X2independently represent hydrogen, halogen, nitro, cyano, thiocyano, hydroxy, mercapto, sulfonate, formyl, halogenformyl, azido, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C3alkyl, C3-C6cycloalkenyl, C3-C6cycloalkenylC1-C3alkyl, -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'=N-O-R", heterocyclyl, heterocyclylC1-C3alkyl, aryl, arylC1-C3alkyl, amino, aminoC1-C3alkyl, aminocarbonylC1-C3alkyl, aminocarbonyloxyC1-C3alkyl, aminothiocarbonyloxyC1-C3alkyl, aminosulfonyl or aminosulfonyloxyC1-C3alkyl, wherein,

[0053] said "C1-C6alkyl", "C2-C6alkenyl" or "C2-C6alkynyl" is independently unsubstituted or substituted with 1, 2 or 3 radicals selected from halogen, cyano, hydroxy, mercapto, carboxy, -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-C3alkyl)-(CO)OH or -O-(C1-C3alkyl)-(CO)OR",

[0054] said "C3-C6cycloalkyl", "C3-C6cycloalkylC1-C3alkyl", "C3-C6cycloalkenyl", "C3-C6cycloalkenylC1-C3alkyl", "heterocyclyl", "heterocyclylC1-C3alkyl", "aryl" or "arylC1-C3alkyl" is independently unsubstituted or substituted with 1, 2 or 3 radicals selected from oxo, halogen, cyano, nitro, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, halogen-C1-C6alkyl, halogen-C2-C6alkenyl, halogen-C2-C6alkynyl, halogen-C3-C6cycloalkyl, C3-C6cycloalkyl substituted with C1-C6alkyl, -OR 14 14 14 14 14 14 , -N(R 11 )2 or -O-(C1-C3alkyl)-(CO)OR 11 , or two adjacent carbon atoms in the ring form a fused ring with -OCH2CH2- or -OCH2O- which are unsubstituted or substituted with halogen,

[0055] said "amino", "aminoC1-C3alkyl", "aminocarbonylC1-C3alkyl", "aminocarbonyloxyC1-C3alkyl", "aminothiocarbonyloxyC1-C3alkyl", "aminosulfonyl" or "aminosulfonyloxyC1-C3alkyl" is independently unsubstituted or substituted with 1, 2 or 3 radicals selected from -R 11 11 11 11 11 11 12 12 ​​​​​​​​​​​​Substituted by one or two groups of )2;

[0056] 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)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-.

[0057] "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 13The "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-.

[0058] 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. 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, 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 14substituted by at least one group selected from the group consisting of halogen, cyano, nitro, C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C3-C8-cycloalkyl, halogen-C1-C8-alkyl, halogen-C2-C8-alkenyl, halogen-C2-C8-alkynyl, halogen-C3-C8-cycloalkyl, C3-C8-cycloalkyl substituted by C1-C8-alkyl, -OR

[0059] W4, W5 independently of each other represent hydrogen, C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, heterocyclyl, aryl, wherein said "C1-C8-alkyl", "C2-C8-alkenyl" or "C2-C8-alkynyl" is independently of each other unsubstituted or substituted by at least one group selected from the group consisting of halogen, cyano, nitro, C3-C8-cycloalkyl, tri C1-C8-alkylsilyl, C3-C8-cycloalkenyl, heterocyclyl, aryl, wherein said "C3-C8-cycloalkyl", "C3-C8-cycloalkenyl", "heterocyclyl" or "aryl" is independently of each other unsubstituted or substituted by at least one group selected from the group consisting of oxo, halogen, cyano, nitro, C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C3-C8-cycloalkyl, halogen-C1-C8-alkyl, halogen-C2-C8-alkenyl, halogen-C2-C8-alkynyl, halogen-C3-C8-cycloalkyl, C3-C8-cycloalkyl substituted by 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 , or adjacent carbon atoms on the ring form a fused ring with -OCH2CH2- or -OCH2O- which are unsubstituted or substituted by halogen;

[0060] or NW4W5 represents or which is unsubstituted or substituted by at least one group selected from the group consisting of oxo, C1-C8-alkyl or C1-C8-alkoxycarbonyl;

[0061] X 11each independently represents hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, C3-C8cycloalkylC1-C8alkyl, C3-C8cycloalkenyl, C3-C8cycloalkenylC1-C8alkyl, heterocyclyl, heterocyclylC1-C8alkyl, aryl or arylC1-C8alkyl, wherein the "C3-C8cycloalkyl", "C3-C8cycloalkylC1-C8alkyl", "C3-C8cycloalkenyl", "C3-C8cycloalkenylC1-C8alkyl", "heterocyclyl", "heterocyclylC1-C8alkyl", "aryl" or "arylC1-C8alkyl" is each independently unsubstituted or substituted by at least one radical selected from the group consisting of oxo, halogen, cyano, nitro, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, halogen-C1-C8alkyl, halogen-C2-C8alkenyl, halogen-C2-C8alkynyl, halogen-C3-C8cycloalkyl, C3-C8cycloalkyl substituted by C1-C8alkyl, -OR 14 , -SR 14 , -(CO)OR 14 , -(SO2)R 14 , -N(R 14 )2or -O-(C1-C8alkyl)-(CO)OR 14 , or adjacent carbon atoms in the ring form a fused ring with -OCH2CH2- or -OCH2O- unsubstituted or substituted by halogen;

[0062] X 12 each independently represents C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, C3-C8cycloalkylC1-C8alkyl, C3-C8cycloalkenyl, C3-C8cycloalkenylC1-C8alkyl, heterocyclyl, heterocyclylC1-C8alkyl, aryl or arylC1-C8alkyl, wherein the "C3-C8cycloalkyl", "C3-C8cycloalkylC1-C8alkyl", "C3-C8cycloalkenyl", "C3-C8cycloalkenylC1-C8alkyl", "heterocyclyl", "heterocyclylC1-C8alkyl", "aryl" or "arylC1-C8alkyl" is each independently unsubstituted or substituted by at least one radical selected from the group consisting of oxo, halogen, cyano, nitro, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, halogen-C1-C8alkyl, halogen-C2-C8alkenyl, halogen-C2-C8alkynyl, halogen-C3-C8cycloalkyl, C3-C8cycloalkyl substituted by C1-C8alkyl, -OR 14 , -SR 14 , -(CO)OR 14 , -(SO2)R 14 , -N(R 14 )2or -O-(C1-C8alkyl)-(CO)OR14 , or two adjacent carbon atoms in the ring form a fused ring with -OCH2CH2- or -OCH2O- which are unsubstituted or substituted with halogen;

[0063] X 13 , X 14 each independently represents hydrogen, halogen, cyano, C1-C8alkoxy, C1-C8alkoxyC1-C8alkyl, C1-C8alkylcarbonyl, C1-C8alkoxycarbonyl, C1-C8alkylsulfonyl, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, C3-C8cycloalkylC1-C8alkyl, C3-C8cycloalkenyl, C3-C8cycloalkenylC1-C8alkyl, aryl, arylC1-C8alkyl, heterocyclyl or heterocyclylC1-C8alkyl, or the groups CX 13 X 14 together form a 5- to 8-membered carbocyclic or oxygen-, sulfur- or nitrogen-containing heterocyclic ring, or the groups NX 13 X 14 together form wherein said "C1-C8alkyl", "C2-C8alkenyl" or "C2-C8alkynyl" is unsubstituted or substituted with halogen, said "C3-C8cycloalkyl", "C3-C8cycloalkylC1-C8alkyl", "C3-C8cycloalkenyl", "C3-C8cycloalkenylC1-C8alkyl", "aryl", "arylC1-C8alkyl", "heterocyclyl" or "heterocyclylC1-C8alkyl" is unsubstituted or substituted with at least one member selected from the group consisting of oxo, halogen, cyano, nitro, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, halogenC1-C8alkyl, halogenC2-C8alkenyl, halogenC2-C8alkynyl, halogenC3-C8cycloalkyl, C3-C8cycloalkyl substituted with C1-C8alkyl, -OR 14 , -SR 14 , -(CO)OR 14 , -(SO2)R 14 , -N(R 14 )2 or -O-(C1-C8alkyl)-(CO)OR 14 , or two adjacent carbon atoms in the ring form a fused ring with -OCH2CH2- or -OCH2O- which are unsubstituted or substituted with halogen, said "5- to 8-membered carbocyclic or oxygen-, sulfur- or nitrogen-containing heterocyclic ring" is unsubstituted or substituted with at least one member selected from the group consisting of C1-C8alkyl, C1-C8alkoxycarbonyl or benzyl, or forms a fused ring structure with aryl or heterocyclyl; said is unsubstituted or substituted by at least one group selected from oxo, C1-C8alkyl or C1-C8alkoxycarbonyl.

[0064] In another embodiment, W3independently represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C3-C6cycloalkenyl, heterocyclyl, aryl, wherein said "C1-C6alkyl", "C2-C6alkenyl" or "C2-C6alkynyl" is independently unsubstituted or substituted by 1, 2 or 3 groups selected from halogen, cyano, nitro, C3-C6cycloalkyl, tri C1-C6alkylsilyl, C3-C6cycloalkenyl, heterocyclyl, aryl, wherein said "C3-C6cycloalkyl", "C3-C6cycloalkenyl", "heterocyclyl" or "aryl" is independently unsubstituted or substituted by 1, 2 or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, halogenated C1-C6alkyl, halogenated C2-C6alkenyl, halogenated C2-C6alkynyl, halogenated C3-C6cycloalkyl, C3-C6cycloalkyl substituted by C1-C6alkyl, -OR 14 , -SR 14 , -(CO)OR 14 , -(SO2)R 14 , -N(R 14 )2or -O-(C1-C6alkyl)-(CO)OR 14 , or the two adjacent carbon atoms of the ring form a fused ring with -OCH2CH2- or -OCH2O- unsubstituted or substituted by halogen;

[0065] W4, W5independently represent hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C3-C6cycloalkenyl, heterocyclyl, aryl, wherein said "C1-C6alkyl", "C2-C6alkenyl" or "C2-C6alkynyl" is independently unsubstituted or substituted by 1, 2 or 3 groups selected from halogen, cyano, nitro, C3-C6cycloalkyl, tri C1-C6alkylsilyl, C3-C6cycloalkenyl, heterocyclyl, aryl, C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, haloC1-C6alkyl, haloC2-C6alkenyl, haloC2-C6alkynyl, haloC3-C6cycloalkyl, C3-C6cycloalkyl substituted with C1-C6alkyl, -OR 14 , -SR 14 , -(CO)OR 14 , -(SO2)R 14 , -N(R 14 )2, or -O-(C1-C6alkyl)-(CO)OR 14 , or two adjacent carbon atoms in the ring form a fused ring with -OCH2CH2- or -OCH2O- which are unsubstituted or substituted with halogen;

[0066] or NW4W5represents or which is unsubstituted or substituted with 1, 2 or 3 radicals selected from oxo, C1-C6alkyl or C1-C6alkoxycarbonyl;

[0067] X 11 independently represent hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl, C3-C6cycloalkenyl, C3-C6cycloalkenylC1-C6alkyl, heterocyclyl, heterocyclylC1-C6alkyl, aryl or arylC1-C6alkyl, wherein said "C3-C6cycloalkyl", "C3-C6cycloalkylC1-C6alkyl", "C3-C6cycloalkenyl", "C3-C6cycloalkenylC1-C6alkyl", "heterocyclyl", "heterocyclylC1-C6alkyl", "aryl" or "arylC1-C6alkyl" are independently unsubstituted or substituted with 1, 2 or 3 radicals selected from oxo, halogen, cyano, nitro, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, haloC1-C6alkyl, haloC2-C6alkenyl, haloC2-C6alkynyl, haloC3-C6cycloalkyl, C3-C6cycloalkyl substituted with C1-C6alkyl, -OR 14 , -SR 14 , -(CO)OR 14 , -(SO2)R 14 , -N(R 14 )2, or -O-(C1-C6alkyl)-(CO)OR 14One, 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-.

[0068] 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-.

[0069] 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- to 8-membered saturated carbon rings, Or the NX group 13 X 14 Together 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. "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, said..." It is either unsubstituted or substituted with one, two, or three groups selected from oxo, C1-C6 alkyl, or C1-C6 alkoxycarbonyl.

[0070] 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. Wherein, the “C1-C6 alkyl,” “C2-C6 alkenyl,” or “C2-C6 alkynyl” are independently unsubstituted or selected from halogens, cyano, nitro, C3-C6 cycloalkyl, triC1-C6 alkylsilyl, C3-C6 cycloalkenyl, heterocyclic, aryl, substituted by 1, 2 or 3 radicals independently selected from oxo, halogen, cyano, nitro, d-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, halo-Ci-C6-alkyl, halo-C2-C6-alkenyl, halo-C2-C6-alkynyl, halo-C3-C6-cycloalkyl, C3-C6-cycloalkyl substituted by d-C6-alkyl, -OR 14 , -SR 14 , -(CO)OR 14 , -(SO2)R 14 , -N(R 14 )2 or -0-(Ci-C3-alkyl)-(CO)OR 14 , or form a fused ring with the two adjacent carbon atoms in the ring which is unsubstituted or substituted by halogen;

[0071] W4, W5 independently from each other represent hydrogen, d-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, heterocyclyl, aryl, wherein said "Ci-C6-alkyl", "C2-C6-alkenyl" or "C2-C6-alkynyl" independently from each other is unsubstituted or substituted by 1, 2 or 3 radicals independently selected from halogen, cyano, nitro, C3-C6-cycloalkyl, tri-Ci-C6-alkylsilyl, C3-C6-cycloalkenyl, heterocyclyl, aryl, substituted by 1, 2 or 3 radicals independently selected from oxo, halogen, cyano, nitro, d-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, halo-Ci-C6-alkyl, halo-C2-C6-alkenyl, halo-C2-C6-alkynyl, halo-C3-C6-cycloalkyl, C3-C6-cycloalkyl substituted by d-C6-alkyl, -OR 14 , -SR 14 , -(CO)OR 14 , -(SO2)R 14 , -N(R 14 )2 or -0-(Ci-C3-alkyl)-(CO)OR 14 , or form a fused ring with the two adjacent carbon atoms in the ring which is unsubstituted or substituted by halogen;

[0072] or NW4W5 represents or which is unsubstituted or substituted by 1, 2 or 3 radicals selected from oxo, C1-C6alkyl or C1-C6alkoxycarbonyl;

[0073] X 11 each independently represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C3alkyl, C3-C6cycloalkenyl, C3-C6cycloalkenylC1-C3alkyl, heterocyclyl, heterocyclylC1-C3alkyl, aryl or arylC1-C3alkyl, wherein said "C3-C6cycloalkyl", "C3-C6cycloalkylC1-C3alkyl", "C3-C6cycloalkenyl", "C3-C6cycloalkenylC1-C3alkyl", "heterocyclyl", "heterocyclylC1-C3alkyl", "aryl" or "arylC1-C3alkyl" is each independently unsubstituted or substituted by 1, 2 or 3 radicals selected from oxo, halogen, cyano, nitro, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, halogen-C1-C6alkyl, halogen-C2-C6alkenyl, halogen-C2-C6alkynyl, halogen-C3-C6cycloalkyl, C3-C6cycloalkyl substituted by C1-C6alkyl, -OR 14 , -SR 14 , -(CO)OR 14 , -(SO2)R 14 , -N(R 14 )2 or -O-(C1-C3alkyl)-(CO)OR 14 or form a fused ring with the carbon atoms to which they are attached, which are unsubstituted or substituted by halogen;

[0074] X 12 each independently represents C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C3alkyl, C3-C6cycloalkenyl, C3-C6cycloalkenylC1-C3alkyl, heterocyclyl, heterocyclylC1-C3alkyl, aryl or arylC1-C3alkyl, wherein said "C3-C6cycloalkyl", "C3-C6cycloalkylC1-C3alkyl", "C3-C6cycloalkenyl", "C3-C6cycloalkenylC1-C3alkyl", "heterocyclyl", "heterocyclylC1-C3alkyl", "aryl" or "arylC1-C3alkyl" is each independently unsubstituted or substituted by 1, 2 or 3 radicals selected from oxo, halogen, cyano, nitro, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, halogen-C1-C6alkyl, halogen-C2-C6alkenyl, halogen-C2-C6alkynyl, halogen-C3-C6cycloalkyl, C3-C6cycloalkyl substituted by C1-C6alkyl, -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 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- to 8-membered saturated carbon rings, Or the NX group 13 X 14 Together 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. " is unsubstituted or substituted by one, two or three radicals selected from C1-C6alkyl, C1-C6alkoxycarbonyl or benzyl, or forms a fused ring structure with phenyl or thienyl; said " is unsubstituted or substituted by one, two or three radicals selected from C1-C6alkyl, C1-C6alkoxycarbonyl or benzyl, or forms a fused ring structure with phenyl or thienyl; said

[0076] R 11 independently of one another represent C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, C3-C8cycloalkylC1-C8alkyl, C3-C8cycloalkenyl, C3-C8cycloalkenylC1-C8alkyl, phenyl or benzyl, wherein the "C1-C8alkyl", "C2-C8alkenyl" or "C2-C8alkynyl" are each independently unsubstituted or substituted by halogen, and the "phenyl" or "benzyl" are each independently unsubstituted or substituted by at least one radical selected from halogen, cyano, nitro, C1-C8alkyl, halogen-C1-C8alkyl, C1-C8alkoxycarbonyl, C1-C8alkylthio, C1-C8alkylsulfonyl, C1-C8alkoxy or halogen-C1-C8alkoxy;

[0077] R 12 independently of one another represent hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C1-C8alkoxy, C1-C8alkylsulfonyl, C3-C8cycloalkyl, C3-C8cycloalkylC1-C8alkyl, C3-C8cycloalkenyl or C3-C8cycloalkenylC1-C8alkyl, or a radical N(R 12 )2or N(R 12 )2in the radicals -(CO)N(R 12 )2or -(SO2)N(R 12 )2independently of one another represent which is unsubstituted or substituted by at least one radical selected from oxo, C1-C8alkyl or C1-C8alkoxycarbonyl;

[0078] R 13 independently of one another represent C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, phenyl or phenyl substituted by at least one radical selected from halogen, cyano, nitro, C1-C8alkyl, halogen-C1-C8alkyl, C1-C8alkoxy, halogen-C1-C8alkoxy, C1-C8alkoxycarbonyl, C1-C8alkylthio, C1-C8alkylsulfonyl or phenoxy substituted by at least one radical selected from halogen, cyano, nitro, C1-C8alkyl, halogen-C1-C8alkyl, C1-C8alkoxy or halogen-C1-C8alkoxy;

[0079] R 14independently of each other represent hydrogen, C1-C8alkyl, halogenated C1-C8alkyl, phenyl or phenyl substituted by at least one radical selected from the group consisting of halogen, cyano, nitro, C1-C8alkyl, halogenated C1-C8alkyl, C1-C8alkyloxycarbonyl, C1-C8alkylthio, C1-C8alkylsulfonyl, C1-C8alkoxy or halogenated C1-C8alkoxy.

[0080] In another particular embodiment, R 11 independently of each other represent C1-C6alkyl, C2-C6alkenyl, C2-C6alkinyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl, C3-C6cycloalkenyl, C3-C6cycloalkenylC1-C6alkyl, phenyl or benzyl, wherein the "C1-C6alkyl", "C2-C6alkenyl" or "C2-C6alkinyl" are independently of each other unsubstituted or substituted by halogen, and the "phenyl" or "benzyl" are independently of each other unsubstituted or substituted by 1, 2 or 3 radicals selected from the group consisting of halogen, cyano, nitro, C1-C6alkyl, halogenated C1-C6alkyl, C1-C6alkyloxycarbonyl, C1-C6alkylthio, C1-C6alkylsulfonyl, C1-C6alkoxy or halogenated C1-C6alkoxy;

[0081] R 12 independently of each other represent hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkinyl, C1-C6alkoxy, C1-C6alkylsulfonyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl, C3-C6cycloalkenyl or C3-C6cycloalkenylC1-C6alkyl, or a radical N(R 12 )2or -(SO2)N(R 12 )2, wherein the radicals N(R 12 )2independently of each other represent which is unsubstituted or substituted by 1, 2 or 3 radicals selected from the group consisting of oxo, C1-C6alkyl or C1-C6alkyloxycarbonyl;

[0082] R 13 independently of each other represent C1-C6alkyl, C2-C6alkenyl, C2-C6alkinyl, C3-C6cycloalkyl, phenyl or phenyl substituted by 1, 2 or 3 radicals selected from the group consisting of halogen, cyano, nitro, C1-C6alkyl, halogenated C1-C6alkyl, C1-C6alkyloxycarbonyl, C1-C6alkylthio, C1-C6alkylsulfonyl, C1-C6alkoxy or halogenated C1-C6alkoxy, or a radical N(R

[0083] R14 independently of each other, represent hydrogen, C1-C6-alkyl, halo-C1-C6-alkyl, phenyl or phenyl substituted by 1, 2 or 3 radicals selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6-alkyl, C1-C6-alkyloxy- carbonyl, C1-C6-alkylthio, C1-C6-alkylsulfonyl, C1-C6-alkyloxy or halo-C1-C6- alkoxy.

[0084] In another embodiment, R 11 independently of each other, represent 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, phenyl, benzyl, wherein the "C1-C6-alkyl", "C2-C6-alkenyl" or "C2-C6-alkynyl" are independently of each other unsubstituted or substituted by halogen, the "phenyl" or "benzyl" are independently of each other unsubstituted or substituted by 1, 2 or 3 radicals selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6-alkyl, C1-C6-alkyloxy- carbonyl, C1-C6-alkylthio, C1-C6-alkylsulfonyl, C1-C6-alkyloxy or halo-C1-C6- alkoxy;

[0085] R 12 independently of each other, represent hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkyloxy, C1-C6-alkylsulfonyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C3-alkyl, C3-C6-cycloalkenyl or C3-C6-cycloalkenyl-C1-C3-alkyl, or a radical N(R 12 )2 or -(SO2)N(R 12 )2, wherein the radicals N(R 12 )2 independently of each other represent which is unsubstituted or substituted by 1, 2 or 3 radicals selected from the group consisting of oxo, C1-C6-alkyl or C1-C6-alkyloxycarbonyl;

[0086] R 13 independently of each other, represent C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl or phenyl substituted by 1, 2 or 3 radicals selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6-alkyl, C1-C6-alkyloxy- carbonyl, C1-C6-alkylthio, C1-C6-alkylsulfonyl or phenyloxy substituted by 1, 2 or 3 radicals selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, halo-C1-C6-alkyl, C1-C6-alkyloxy or halo-C1-C6-alkyloxy;

[0087] R 14 independently of one another represent hydrogen, C1-C6alkyl, halogenated C1-C6alkyl, phenyl or phenyl substituted by 1, 2 or 3 radicals selected from the group consisting of halogen, cyano, nitro, C1-C6alkyl, halogenated C1-C6alkyl, C1-C6alkyloxycarbonyl, C1-C6alkylsulfanyl, C1-C6alkylsulfonyl, C1-C6alkyloxy or halogenated C1-C6alkyloxy.

[0088] In the definition of the compounds of the general formulae described above and in all the structural formulae below, the professional terms used, whether used alone or in a composite, represent the following substituents: alkyl groups having more than two carbon atoms can be straight-chained or branched. As in the composite "alkyl-(CO)OR 11 ", the alkyl group can be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, etc. Alkyl groups are, for example, C1alkyl - methyl; C2alkyl - ethyl; C3alkyl - propyl, such as n-propyl or isopropyl; C4alkyl - butyl, such as n-butyl, isobutyl, tert-butyl or 2-butyl; C5alkyl - pentyl, such as n-pentyl; C6alkyl - hexyl, such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Similarly, alkenyl is, for example, ethenyl, allyl, 1 -methylprop-2-en-1 -yl, 2-methylprop-2-en-1 -yl, but-2-en-1 -yl, but-3-en-1 -yl, 1 -methylbut-3-en-1 -yl and 1 -methylbut-2-en-1 -yl. Alkynyl is, for example, ethynyl, propargyl, but-2-yn-1 -yl, but-3-yn-1 -yl, 1 -methylbut-3-yn-1 -yl. The multiple bonds can be in any position of each unsaturated group. 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 bonds can be in any position. Halogen is fluorine, chlorine, bromine or iodine.

[0089] Unless otherwise specified, "aryl" as used herein includes, but is not limited to, phenyl, naphthyl, " Heterocyclyl" includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups " Heterocyclyl" includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups

[0090] If a group is substituted by a group, this is to be understood as meaning that the group is substituted by one or more, identical or different, groups selected from those mentioned. In addition, the same or different substituents contained in the same or different substituents are each selected independently of one another, can be identical or different. The same applies to ring systems formed by different atoms and units. At the same time, the scope of the claims is to exclude compounds which are chemically unstable under standard conditions, as known to the person skilled in the art.

[0091] In addition, "substituted by at least one group" according to the application means, unless specifically limited, substitution by 1, 2, 3, 4 or 5 groups; groups not marked with a specific position of attachment (including heterocyclyl, aryl, etc.) can be attached at any position, including attachment to a C or N; if it is substituted, the substituents can likewise be substituted at any position, provided that the rules for bond connectivity are followed. For example, a heteroaryl group substituted by 1 methyl group may represent, for example and the like.

[0092] It is noted that when the carbon atom (C*) attached to X1and X2in general formula I is a chiral center (i.e. X1and X2are not the same), it is in the R configuration or the S configuration.

[0093] In the present application, the stereochemical configuration at the position marked*in formula I is determined according to the Cahn-Ingold-Prelog system as predominantly (R) or (S), however the subject matter of the present application also relates to all stereoisomers of formula I, including other positions, and mixtures thereof. Such compounds of formula I include, for example, one or more additional asymmetric carbon atoms or other double bonds not specifically mentioned in formula I. It is to be understood that the present application includes pure isomers and mixtures of the pure isomers in varying degrees of enrichment, wherein the asymmetric carbon atom at the position marked*is in the R-configuration or the S-configuration, or in mixtures, the compounds or compounds of the same chemical structure have the R-configuration or the S-configuration at the position marked*, or predominantly in the proportion of compounds having the R-configuration or the S-configuration (at least 60% R-configuration or S-configuration), while the other asymmetric carbon atoms can be present in racemic form, or can also be resolved to varying degrees. As long as the stereochemical configuration at the position marked*is met, possible stereoisomers defined by the particular spatial form, such as enantiomers, diastereomers, Z- and E-isomers, are included in formula I and can be obtained from mixtures of stereoisomers in a conventional manner, or can also be prepared by stereoselective reactions in combination with the use of stereochemically pure starting materials.

[0094] If various functional groups are present, the present application also includes any keto and enol tautomeric forms and mixtures and salts thereof.

[0095] The stereoisomers can be obtained from the mixtures obtained in the preparation by optical resolution. Likewise, the stereoisomers can be prepared selectively by using stereoselective reactions and using optically active starting materials and / or auxiliaries. For optical resolution, it is generally possible to employ conventional methods (cf. Textbooks of Stereochemistry), for example the following methods for the resolution of mixtures into diastereomers, for example physical methods such as crystallization, chromatography, in particular column chromatography and high-pressure liquid chromatography, distillation methods, which are carried out under reduced pressure if appropriate, extraction and other methods, usually with chromatographic separation on a chiral stationary phase, it being possible to separate the residual mixtures of enantiomers. Suitable for preparative amounts or for industrial scale are methods such as crystallization of diastereomeric salts, which can be obtained from the compounds with optically active acids and, if acidic groups are present, if appropriate with optically active bases.

[0096] The process for the preparation of the heterocyclic ring-substituted aromatic compounds comprises the following steps:

[0097] The compound according to general formula II is reacted with a compound according to general formula III to obtain a compound according to general formula I, the chemical reaction equation of which is as follows:

[0098]

[0099] wherein Hal represents halogen, preferably CI; the definitions of substituents X1, X2, R1, R2, R3, R4, M1, M2, Y and Z are as described above;

[0100] 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 alkyl amines, preferably tri-(C1-C6)-alkyl amines, for example triethylamine, trimethylamine, N-ethyldiisopropylamine);

[0101] 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.

[0102] The compound according to general formula II can be prepared according to the methods described in WO12130798, WO1404882, WO14048882, WO18228985, WO18228986, WO19034602 or WO19145245, etc.

[0103] A herbicidal composition comprising a herbicidally effective amount of at least one of the heterocyclic ring-substituted aromatic compounds, preferably, further comprising a formulation auxiliary.

[0104] A method of controlling weeds, which comprises applying to the plants or the area of weeds a herbicidally effective amount of at least one of the heterocyclic substituted aromatic compounds or the herbicidal composition.

[0105] Use of at least one of the heterocyclic substituted aromatic compounds or the herbicidal composition for controlling weeds, preferably for controlling weeds in useful crops, which are genetically modified crops or crops treated by genome editing technology.

[0106] The compounds of the formula I of the present application have outstanding herbicidal activity against a large number of economically important monocotyledonous and dicotyledonous harmful plants. The active substances of the present application are also effective against perennial weeds which grow from rhizomes, tubers or other perennial organs and are difficult to control. In this connection, it is generally immaterial whether the substances are used before sowing, before germination or after germination. Particular mention comes to representatives of the group of monocotyledonous and dicotyledonous weeds which can be controlled by the compounds of the present application without limitation to the specified species. Examples of weed species against which the active substances are effective include the following monocotyledons: annuals of the genera Avena, Secale, Phalaris, Alopecurus, Eleusine, Echinochloa, Digitaria, Cynodon and Cyperus, and the perennials of the genera Agropyron, Cynodon, Imperata and Sorghum, and the perennial Cyperus.

[0107] As regards dicotyledonous weed species, the activity can extend to species such as annuals of the genera Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Raphanus, Ipomoea, Sida, Matricaria and Abutilon, and the perennials of the genera Convolvulus, Cirsium, Rumex and Artemisia. The active substances of the present application are effective in controlling harmful plants under the conditions prevailing at the time of sowing of rice, for example Echinochloa, Alocasia, Alisma, Eleocharis, Glyceria and Cyperus. If the compounds of the present application are applied to the soil surface before germination, the seedlings of the weeds can be completely prevented from growing or growth can be stopped at the stage of the cotyledon and finally the plants can die completely after three to four weeks. The activity of the compounds of the present application is particularly good against the following plants, Apluda, Lamium, Polygonum, Stellaria, Hedera helix, Veronica arvensis, Veronica persica, Viola tricolor and Amaranthus, Galium and Kochia.

[0108] Although the compounds of the present application have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, they do not damage or damage only insignificantly important economic crop plants, for example wheat, barley, rye, rice, maize, sugar beet, cotton and soybean. In particular, there is a very good compatibility with cereal crops, for example wheat, barley and maize, in particular wheat. The compounds of the present application are therefore very suitable for the selective control of unwanted plants in crop plants or ornamental plants.

[0109] Due to their herbicidal properties, these active substances can be used for controlling harmful plants in genetically engineered plants which are known or will be developed in the future. Genetically modified plants usually have superior properties, for example resistance to certain pesticides, particularly to certain herbicides, resistance to plant diseases or to the causative microorganisms of plant diseases, for example to certain insects or fungi, bacteria or viruses. Other special properties are associated with the following properties of the products, for example quantity, quality, storage stability, components and special ingredients. Thus, genetically modified plant products are known which have an increased starch content or an improved starch quality or a different fatty acid composition.

[0110] The compounds of the formula I or their salts according to the application are preferably used in the cultivation of economically important genetically modified crops and ornamental plants, for example cereals, such as wheat, barley, rye, oats, millet, rice, cassava and maize, or in the cultivation of sugar beets, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetable plants. The compounds of the formula I are preferably used as herbicides in the cultivation of useful plants which are resistant to the action of herbicides or which have been rendered resistant to the action of herbicides by genetic engineering.

[0111] Traditional methods for breeding plants with improved properties compared to known plants include, for example, traditional crossbreeding methods and breeding of mutants. In other words, new plants with improved properties can also be obtained by means of methods of genetic engineering (cf., for example, EP-0221044A, EP-0131624A). For example, several methods have been described:

[0112] - in order to improve starch synthesis in plants, crop plants are modified by genetic engineering (for example WO 92 / 11376, WO 92 / 14827, WO 91 / 19806);

[0113] - genetically modified crop plants which are resistant to certain herbicides, for example to herbicides based on glufosinate (for example EP-0242236A, EP-0242246A) or to herbicides based on glyphosate (WO 92 / 00377) or to herbicides based on sulfonylurea (EP-0257993A, US-5013659A);

[0114] - genetically modified crop plants, for example of cotton, which are capable of producing toxins of Bacillus thuringiensis (Bt toxins) which protect the plants from the attack of certain pests (EP-0142924A, EP-0193259A);

[0115] - genetically modified crop plants which have an improved fatty acid composition (WO 91 / 13972).

[0116] A number of molecular biological techniques are known which make it possible to produce transgenic plants with improved properties (see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Edition, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York; or Winnacker "Gene und Klone" [Genes and Clones], VCH Weinheim, 2nd Edition 1996 or Christou, Trends in Plant Science 1 (1996) 423-431)). In order to achieve the genetic engineering operations, it is possible to introduce nucleic acid molecules into plasmids, to mutate or to change sequences by recombination of DNA sequences. Using the standard methods described above, it is possible, for example, to exchange substrates, to remove partial sequences or to add natural or synthetic sequences. In order to join DNA fragments to one another, it is possible to attach linkers or adaptors to the fragments.

[0117] It is possible to produce plant cells with reduced activity of a gene product, for example by expressing at least one suitable antisense-RNA, sense-RNA to achieve the effect of co-suppression, or by expressing at least one suitably constructed ribozyme which specifically cleaves the transcript of the gene product in question.

[0118] For this purpose, it is possible to use DNA molecules which comprise the entire coding sequence of the gene product, including any flanking sequences which can be present, and DNA molecules which comprise only a part of the coding sequence, these parts having to be sufficiently long to achieve the effect of antisense in the cell. It is also possible to use sequences which have a high degree of homology with the coding sequence of the gene product but are not identical.

[0119] When nucleic acid molecules are expressed in plants, the synthesized proteins can be localized in any desired plant cell compartment. However, in order to be localized in a particular compartment, it is possible, for example, to link the coding region and DNA sequences which ensure localization in a particular location. These sequences are known to the person 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).

[0120] Using known techniques, it is possible to recombine transgenic plant cells into whole plants. The transgenic plants can be any desired plant species, i.e. monocotyledonous and dicotyledonous plants. In this way, it is possible to obtain transgenic plants with improved properties by overexpression, inhibition or suppression of homologous (= natural) genes or gene sequences, or by expression of heterologous (= foreign) genes or gene sequences.

[0121] When using the active substances according to the application on transgenic crops, in addition to the effect observed on other crops of inhibiting harmful plants, there is often a special effect on the corresponding transgenic crop, for example, the spectrum of weed control can be improved or enlarged, the application rate at the time of application can be improved, the combination of the preferred transgenic crop's resistance and the herbicide's performance is very good, and the growth and yield of the transgenic crop plant is influenced. The use of the compounds according to the application as herbicides for controlling harmful plants in transgenic crop plants is therefore also provided.

[0122] In addition, the compounds according to the application can significantly regulate the growth of crop plants. By regulating the components involved in plant metabolism, the use of these compounds allows targeted control of the plant and promotes harvesting, for example, by drying and dwarfing the growth of the plant. Furthermore, they are suitable for regulating and inhibiting the growth of undesired plants without destroying the growth of the crop. Inhibition of the growth of the plant plays a very important role in many monocotyledonous and dicotyledonous crops, since it can reduce or completely prevent lodging.

[0123] The compounds according to the application can be applied using the usual formulations, using wettable powders, emulsifiable concentrates, sprayable solutions, powders or granules. The application therefore also provides herbicidal compositions comprising the compounds of the formula I. The compounds of the formula I can be formulated in various ways depending on the usual biological and / or chemical-physical parameters. Suitable examples of formulation types are: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates (SL), emulsifiable concentrates (EC), emulsions, for example oil-in-water and water-in-oil (EW), sprayable solutions, suspension concentrates (SC), dispersible oil suspensions (OD), suspensions in oil or water, solutions of miscible oils, powders (DP), capsule suspensions (CS), seed dressing compositions, granules for spreading and soil application, injection granules, coating granules and absorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV (ultra-low-volume) formulations, microencapsulations and wax formulations. These individual formulation types are known and are described, for example, in Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th edition 1986; Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y., 1973; K. Martens, “Spray Drying” handbook, 3rd edition 1979, G. Goodwin Ltd. London.

[0124] Necessary formulation aids, such as inert substances, surfactants, solvents and other additives are likewise known and are described, for example, in Watkins' "Handbook of Insecticide Dusts and Bait Application", 2nd Ed., Darland Books, Caldwell N.J.; H. v. 01 phen "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley and Sons, N.Y.; C. Marsden "Solvents Guide", 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood N.J.; Sisley and Wood "Encyclopedia of Surfactants", Chemical Publishing Co., N.Y. 1964; [Oxirane adduct surfactants], Wiss. Verlagagesell. Stuttgart 1976; Winnacker-Kϋchler "Chemische Technologie" [Chemical Technology], Vol. 7, C. Hauser Verlag Munich, 4th Ed. 1986.

[0125] Wettable powders are capable of being dispersed in water to give uniform, fine particles of active substance, and in addition to the active material, comprise a diluent, or inert substance, ionic and non-ionic surfactants (wetting agents, dispersing agents), for example polyethoxyalkylphenols, polyethoxy fatty alcohols, polyoxyethyl fatty amines, fatty alcohol polyglycol ether sulphates, alkyl sulphonates, alkylphenyl sulphonates, sodium lignosulphonate, sodium 2,2'-dinaphthylmethane-6,6'-disulphonate, sodium dibutylnaphthalene sulphonate or sodium oleylmethyltauride. To prepare wettable powders, the herbicidal active substance is finely ground, for example using conventional apparatus such as hammer mills, fan mills and jet mills, and the adjuvants are mixed in simultaneously or sequentially.

[0126] Concentrated emulsions are prepared by dissolving the active substance in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatic or hydrocarbon compounds or mixtures of solvents, and adding one or more ionic and / or non-ionic surfactants (emulsifiers) thereto. Examples of emulsifiers which can be used are, for example, calcium alkylaryl sulphonates, such as calcium dodecylbenzenesulphonate, or non-ionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, such as sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, such as polyoxyethylene sorbitan fatty esters.

[0127] ​The active substances and finely divided solid substances, such as talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth, are ground to a powder. Suspensions based on water or oil can be prepared by wet grinding, for example, using a commercially available pearl mill, with or without the addition of a surfactant of the other formulation type as described above.

[0128] Emulsions, such as oil-in-water emulsions (EW), can be prepared using aqueous organic solvents, using stirrers, colloid mills and / or static mixers, if desired, with the addition of a surfactant of the other formulation type as described above.

[0129] Granules are prepared by spraying the active substance onto adsorptive substances, using inert material granules, or by concentrating the active substance onto the surface of a carrier, such as sand, kaolin, and granulating the inert material by means of a binder, such as polyvinyl alcohol, sodium polyacrylate or mineral oil. Suitable active substances can be granulated using the methods used for the preparation of granules for fertilizers, if desired, with the addition of fertilizers. Water-soluble granules are prepared using the usual methods, such as spray-drying, fluidized-bed granulation, pan granulation, mixing using a high-speed mixer and extrusion without the addition of solid inert material.

[0130] For the preparation of granules using pan, fluidized-bed, extruder and spray-coating methods, reference is made to the processes described, for example, in the "Handbook of Spray Drying", 3rd edition 1979, G. Goodwin Ltd., London; J. E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff; "Perry's Chemical Engineer's Handbook", 5th edition, McGraw-Hill, New York 1973, pages 8-57. For information on the formulation of crop protection products, reference is made, for example, to G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York 1961, pages 181-96 and J. D. Freyer, S. A. Evans, "Manual of Weed Control", 5th edition, Blackwell Scientific Publications, Oxford 1968, pages 101-103.

[0131] Agricultural chemical formulations usually contain from 0.1 to 99 %, in particular from 0.1 to 95 %, by weight, of active substance of the formula I. The concentration of active substance in wettable powders is, for example, from about 10 to 99 %, the usual formulation components making up the remainder to 100 % by weight. The concentration of active substance in emulsifiable concentrates can be from about 1 to 90 %, preferably from 5 to 80 %, by weight. Dustable powders contain from 1 to 30 %, usually preferably from 5 to 20 %, by weight, of active substance, whereas sprayable solutions contain from about 0.05 to 80 %, preferably from 2 to 50 %, by weight, of active substance. The content of active substance in water-suspension granules is, for example, between 1 and 95 %, preferably between 10 and 80 %, by weight, depending on whether the active substance is liquid or solid and on the auxiliaries, fillers, etc. used during granulation. The content of active substance in water-suspension granules is, for example, between 1 and 95 %, preferably between 10 and 80 %, by weight.

[0132] The formulations mentioned additionally can comprise tackifiers, wetting agents, dispersants, emulsifiers, penetration agents, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, antifoams, evaporation inhibitors and, in general, pH and viscosity regulators, which are customary in each case.

[0133] On the basis of these formulations, it is also possible to mix with other pesticidal active substances, such as insecticides, acaricides, herbicides and fungicides, and also with safeners, fertilizers and / or plant growth regulators, either as premixes or as tank mixes.

[0134] 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, naphthalenepropionyl-methyl, R-L-naphthalenepropionyl-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, methylflumethrin, trifluralin, methoxysulfuron, trifluralin, flufenoxuron, flufenoxuron, metolachlor, methylflumethrin, 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, clodinafop-methyl, dichlorophenate, dichlorophenate, 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, DOWCO 535, DK-8910, V-53482, PP-600, MBH-001, KIH-9201, ET-751, KIH-6127 and KIH-2023.

[0135] When used, commercially available formulations are diluted, if necessary, in the usual manner, for example with water in the case of wettable powders, emulsifiable concentrates, suspensions and granules which are suspended in water. Powders, granules for soil application or solutions for spreading and spraying generally do not require further dilution with inert substances before use. The amount of active compound of formula I required depends on the external conditions, for example temperature, humidity, the nature of the herbicide used and so on. It can vary within wide limits, for example between 0.001 and 1.0 kg a.i. / ha, or more of active substance, but is preferably between 0.005 and 750 g a.i. / ha, in particular between 0.005 and 250 g a.i. / ha. DETAILED DESCRIPTION

[0136] The following examples are intended to illustrate the present application and should not be construed as limiting the application in any way. The scope of the patent protection sought for the present application is defined by the claims.

[0137] In view of the economy and diversity of the compounds, we have synthesized a number of compounds, among which some are selected and listed in Table 1 below. The structures of the specific compounds and the corresponding compound information are shown in Table 1-2. The compounds in Table 1 are only for better illustration of the present application, but do not limit the present application, and for those skilled in the art, this should not be understood as limiting the scope of the above-mentioned subject matter of the present application to the following compounds.

[0138] Table 1 Compound Structure

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149] Table 2 Compounds 1 HNMR

[0150]

[0151]

[0152]

[0153] Several methods for preparing the compounds of this application are illustrated in the following Schemes and Examples. Starting materials can be obtained from commercial sources or made by methods known in the art or as illustrated. Those skilled in the art will appreciate that other synthetic routes can be used to synthesize the compounds of this application. Although specific starting materials and conditions are depicted in the Schemes below, other starting materials and conditions can readily be used by one skilled in the art. Variations to the synthetic routes outlined in the Schemes below, or to the reagents and conditions used for their application, are included within the scope of the present application. In addition, the synthetic methods described below can be further modified using conventional chemistry known to those skilled in the art, as described herein. For example, appropriate groups can be protected during the course of a reaction.

[0154] The following examples of processes are provided to further illustrate the preparation of the compounds of the application, the specific materials, amounts and conditions used to carry out the processes are not intended to limit the scope of the application. The reagents used in the synthesis of the compounds shown in the following tables can be purchased from commercial suppliers or can be readily prepared by one of ordinary skill in the art.

[0155] Representative compounds are synthesized as follows, and other compounds are synthesized in a similar manner.

[0156] 1. Synthesis of Compound 5

[0157] Referring to the preparation method of compound 6-7, compound 5-1 was obtained, 5-1 (0.2 g, 0.51 mmol, 1.0 eq), methyl pyruvate (0.15 g, 1.51 mmol, 3 eq), 10 mL of toluene were sequentially added in a 100 mL single-neck flask, and the reaction solution was stirred at room temperature for 10 min. Then triethylamine (0.05 g, 0.51 mmol, 1 eq) was added dropwise into the reaction solution, and the stirring was continued at room temperature for 8 h. LCMS detection showed that the raw material was substantially completely reacted, and a main new peak was generated. The solvent was rotary evaporated, 20 mL of water and ethyl acetate (20 mL*3) were added for extraction, the organic phase was washed with saturated brine (20 mL*3), and the organic phase was concentrated and then mixed with silica gel for column chromatography to obtain compound 5 (0.04 g, 18% yield, colorless oil).

[0158]

[0159] 2. Synthesis of compound 6

[0160] (1) Compound 6-1 (8.3 g, 38 mmol) was dissolved in 200 mL of acetonitrile, and pinacol borate 6-2 (48 g, 1.90 mol) was added, followed by slow dropwise addition of tert-butyl nitrite (7.8 g, 76 mmol), and the reaction was heated to 60 degrees for 12 h. Liquid phase detection showed that the raw material disappeared, the reaction solution was concentrated to obtain a crude product, water was added, and ethyl acetate was extracted, the organic phase was dried and concentrated, and then mixed with silica gel for column chromatography to obtain compound 6-3 (4.8 g, 14.7 mmol), with a yield of 39%.

[0161]

[0162] (2) 6-4 (0.2 g, 1.00 mmol), borate 6-3 (0.49 g, 1.50 mmol) and potassium carbonate (0.41 g, 3.00 mmol) were added to a clean flask, 1,4-dioxane 20 ml and water 2 ml were added, and nitrogen protection was performed for 2-3 times. After the gas extraction was completed, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride dichloromethane complex (44.74 mg, 54.79 umol) was added, and the gas was extracted again. The temperature was increased to 100 degrees overnight, and the reaction was completed. After the control, the solvent was distilled under reduced pressure, and the water was washed with EA extraction 2-3 times, and then the EA phase was washed with saturated brine 2-3 times. Anhydrous sodium sulfate was added to the EA phase for drying, silica gel was added for mixing and column chromatography, and normal phase purification was performed to obtain 6-5 (300 mg, 0.82 mmol).

[0163]

[0164] (2) 6-5 (0.3 g, 0.82 mmol), hydroxylamine hydrochloride (0.28 g, 4.1 mmol) were added into a clean flask, mixed solvent of ethanol and water (10 ml:2 ml) was added, stirred at 80 degrees Celsius for 3 hours, after the reaction was completed, directly stirred sample forward purification to obtain 6-6 (270 mg, 0.80 mmol).

[0165]

[0166] (3) 6-6 (0.27 g, 0.80 mmol), NCS (0.32 g, 2.4 mmol) were added into a clean flask, dissolved in 10 ml of DMF, stirred at 40 degrees Celsius for 3 hours, after the reaction was completed, washed with water and then extracted with EA (extracted with EA for 3 times), then the EA phase was washed with saturated brine for two times, and the white solid 6-7 (290 mg, 0.78 mmol) was obtained after rotary evaporation.

[0167]

[0168] (4) In a 100 mL single-necked flask, compound 6-7 (0.2 g, 0.54 mmol, 1.0 eq), methyl pyruvate (0.17 g, 1.62 mmol, 3 eq), 10 mL of toluene were added in sequence, and the reaction solution was stirred at room temperature for ten minutes. Then triethylamine (0.06 g, 0.54 mmol, 1 eq) was added dropwise into the reaction solution, and the stirring reaction was continued at room temperature for eight hours. LCMS detection showed that the raw material was basically completely reacted, and a main new peak was generated. The solvent was rotary evaporated, 20 mL of water and ethyl acetate (20 mL*3) were added for extraction, the organic phase was washed with saturated brine (20 mL*3), and the organic phase was concentrated and then stirred sample was passed through a column to obtain compound 6 (0.05 g, 23% yield, light yellow oil).

[0169]

[0170] 3. Synthesis of compound 11

[0171] Compound 11-1 was obtained by referring to the preparation method of compound 6-7, then 11-1 (1.0 eq) and triethylamine (3.0 eq) were added in 10 mL of THF at room temperature, and finally methyl pyruvate (1.5 eq) was added, and the stirring reaction was continued at room temperature for 1 h. LCMS detection showed that the raw material was basically completely reacted. Silicon gel was added to the reaction solution, concentrated and stirred sample, and then compound 11 was obtained by normal phase purification.

[0172]

[0173] 4. Synthesis of compound 15

[0174] Into a 100 mL single neck flask, add 15-1 (0.3 g, 0.78 mmol, 1.0 eq), methyl pyruvate (0.24 g, 2.32 mmol, 3 eq), 10 mL of toluene, stir the reaction mixture at room temperature for 10 min. Then add triethylamine (0.08 g, 0.78 mmol, 1 eq) dropwise into the reaction mixture, continue to stir at room temperature for 8 h. LCMS detection of the raw material is basically complete, there is a major new peak generated. Rotary evaporation of the solvent, add 20 mL of water and ethyl acetate (20 mL*3) extraction, the organic phase is washed with saturated brine (20 mL*3), the organic phase is concentrated and then mixed with the column to obtain compound 15 (0.06 g, 25% yield, yellow oil).

[0175]

[0176] 5. Synthesis of compound 19

[0177] Dissolve compound 6-7 (0.15 g, 0.41 mmol) and methyl 2-oxobutanoate (0.19 g, 1.64 mmol) in 15 ml of toluene, stir in an ice water bath until the temperature drops to zero, dissolve triethylamine (50 mg, 0.49 mmol) in toluene, and add it dropwise into the system in an ice water bath. After the addition is complete, remove the ice water bath and stir at room temperature overnight. After the reaction is complete, directly mix the sample and purify by normal phase to obtain compound 19 (35 mg, 0.08 mmol).

[0178]

[0179] 6. Synthesis of compound 23

[0180] Dissolve 300 mg of compound 23-1 in 10 ml of toluene, add ethyl glyoxylate (350 mg, 4 eq) in an ice bath, and stir uniformly. Slowly add 100 mg of triethylamine (1.2 eq) in 2 ml of toluene, and stir at room temperature overnight after the addition is complete. Monitor the disappearance of the raw material and the generation of the product, and purify by normal phase after workup to obtain 180 mg of compound 23 (50% yield).

[0181]

[0182] 7. Synthesis of compound 114

[0183] (1) Dissolve 300 mg of compound 15 in 10 ml of 1,4-dioxane, add 3 eq of hydrobromic acid, and react at 80°C for 3 h. LC-MS detection shows that the reaction is complete. Concentrate under reduced pressure to remove the solvent, add an appropriate amount of water, extract with ethyl acetate three times, combine the organic phases, wash with saturated brine three times, dry over anhydrous sodium sulfate, spin dry, and obtain 240 mg of crude 114-1 (yield 92%), which is directly used in the next step.

[0184]

[0185] (2) 240 mg of compound 114-1 was dissolved in 10 ml of DMF, 2 eq of anhydrous potassium carbonate was added, 1.5 eq of 3-bromopropyl methyl ether was added dropwise at room temperature, and the reaction was allowed to proceed at room temperature for 2 h. LC-MS detection showed that the reaction was complete, an appropriate amount of water was added, and ethyl acetate was extracted three times, the organic phase was combined and washed with 5% salt water three times, and dried over anhydrous sodium sulfate. Separation and purification were performed with a petroleum ether / ethyl acetate system, and the fraction meeting the purity requirement was rotary evaporated to obtain 60 mg of pure product, which was compound 114 (yield 21%).

[0186]

[0187] Biological activity evaluation:

[0188] The activity level criteria for plant destruction (i.e., growth control rate) are as follows:

[0189] 10: complete death;

[0190] 9: growth control rate greater than or equal to 90% and less than 100%;

[0191] 8: growth control rate greater than or equal to 80% and less than 90%;

[0192] 7: growth control rate greater than or equal to 70% and less than 80%;

[0193] 6: growth control rate greater than or equal to 60% and less than 70%;

[0194] 5: growth control rate greater than or equal to 50% and less than 60%;

[0195] 4: growth control rate greater than or equal to 40% and less than 50%;

[0196] 3: growth control rate greater than or equal to 30% and less than 40%;

[0197] 2: growth control rate greater than or equal to 20% and less than 30%;

[0198] 1: growth control rate less than 20%;

[0199] 0: no effect.

[0200] The above growth control rate is fresh weight control rate.

[0201] Post-emergence test experiment:

[0202] Monocotyledonous and dicotyledonous weed seeds (Deschampsia, Galium aparine, Abutilon theophrasti, Galium verum, Stellaria media, Aegopodium podograria, Rorippa indica, Alopecurus myosuroides, Alopecurus japonicus, Eragrostis japonica, Echinochloa oryzicola, Echinochloa crus-galli, Setaria viridis, Setaria pumila, Euphorbia lathyris, Polygonum persicaria, Polygonum convolvulus, Amaranthus retroflexus, Amaranthus hybridus, Commelina communis, Sonchus oleraceus, Convolvulus arvensis, Raphanus raphanistrum, Acalypha australis, Digitaria sanguinalis, Cynodon dactylon, Panicum dichotomiflorum, Cyperus iria, Cyperus difformis, Fimbristylis miliacea, Portulaca oleracea, Xanthium strumarium, Ipomoea hederifolia, Ambrosia artemisiifolia, etc.) and main crop seeds (wheat, corn, rice, soybean, cotton, rapeseed, millet, sorghum, potato, sesame, castor bean, etc.) were placed in plastic pots filled with soil, then covered with 0.5-2 cm of soil, and allowed to grow in a good greenhouse environment. After 2 weeks of sowing, the test plants were treated at the 2-3 leaf stage, and the compounds of the present application were dissolved in acetone, then Tween 80 was added, 1.5 liters / ha of methyl oleate emulsion was used as a synergist, and a certain concentration of solution was prepared by diluting with water, and sprayed onto the plants using a spray tower. After application, the test plants were cultured in the greenhouse for 3 weeks, and the weed control effect was evaluated. The compounds were used at a dosage of 500, 250, 125, 60, 15, 7.5 g a.i. / ha, and the test was repeated three times, with the average value being taken. Representative data are shown in Table 3.

[0203] Table 3: Post-emergence weed test results

[0204]

[0205]

[0206] Pre-emergence test experiment:

[0207] Monocotyledonous and dicotyledonous weed seeds and main crop seeds (wheat, corn, rice, soybean, cotton, rapeseed, millet, sorghum) were placed in plastic pots filled with soil, then covered with 0.5-2 cm of soil, and the compounds of the present application were dissolved in acetone, then Tween 80 was added, and a certain concentration of solution was prepared by diluting with water, and sprayed immediately after sowing. After application, the test plants were cultured in the greenhouse for 4 weeks, and the test results were observed. It was found that most of the compounds of the present application had excellent effects at a dosage of 250 g a.i. / ha, especially for weeds such as Echinochloa crus-galli, Digitaria sanguinalis, Abutilon theophrasti, etc. Many compounds also had good selectivity for corn, wheat, rice, soybean, etc.

[0208] At the same time, through tests of main weeds in wheat and rice fields, it was found that the compounds of the present application generally had good weed control effects, especially for broadleaf weeds such as Sagittaria trifolia, Cyperus iria, Cyperus difformis, Deschampsia, Galium aparine, Stellaria media, Galium verum, Galium verum, and sedge weeds, which had high activity and very good commercial value.

[0209] Meanwhile, through many tests, it is found that the compound and the composition thereof have good selectivity to St. Augustine grass, Bermudagrass, Tall fescue, Bluegrass, Ryegrass, Sea oats and other Gramineae turf, and can prevent and eliminate many key Gramineae weeds and broadleaf weeds. Tests on sugarcane, soybean, cotton, oil sunflower, potato, fruit trees, vegetables and the like under different application modes also show excellent selectivity and commercial value.

Claims

1. A heterocyclic substituted aromatic compound, as shown in general formula I: ， in, Y represents halogen, C1-C8 haloalkyl, or cyano; Z represents halogen; M1, M2each independently represents CR5or N(O) m ; R1, R2, R3, R4, R5 each independently represents hydrogen, halogen, C1-C8 alkyl or -OR 11 wherein said "C1-C8 alkyl" each independently is unsubstituted or substituted with halogen; X1 represents hydrogen, C1-C8 alkyl or C3-C8 cycloalkyl, wherein the "C1-C8 alkyl" is independently unsubstituted or substituted by at least one group selected from halogens; X2represents ; W1 represents O; W2 represents OW3, SW3, or NW4W5; W3represents independently for each occurrence hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl or wherein said "C1-C8alkyl", "C2-C8alkenyl" or "C2-C8alkynyl" is independently for each occurrence unsubstituted or substituted with at least one member selected from the group consisting of halogen, cyano, C3-C8cycloalkyl, aryl, or said "aryl" is unsubstituted or substituted with at least one member selected from the group consisting of halogen. NW4W5 represents which is unsubstituted or substituted by at least one group selected from C1-C8alkyl; X 11 each independently represents C1-C8alkyl, C2-C8alkenyl or C2-C8alkynyl; X 13 , X 14 each independently represents hydrogen, C1-C8alkoxy, C1-C8alkoxyC1-C8alkyl, C1-C8alkyl, C3-C8cycloalkyl, aryl or heterocyclyl, or the groups CX 13 X 14 together form a 5-8 membered carbocyclic ring, wherein said "C1-C8alkyl" is each independently unsubstituted or substituted with halogen, and said "aryl" or "heterocyclyl" is each independently unsubstituted or substituted with at least one group selected from C1-C8alkyl; R 11 each independently represents C1-C8alkyl, C2-C8alkenyl or C2-C8alkynyl; said "C1-C8alkyl", "C2-C8alkenyl" or "C2-C8alkynyl" is each independently unsubstituted or substituted with halogen; m represents 0; wherein the aryl group is phenyl and the heterocyclyl group is or .

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, M1 represents CR5; M2represents CR5or N(O) m .

4. A heterocyclic substituted aromatic compound according to claim 1, characterized in that, R1, R2, R3, R4, R5each independently represents hydrogen, halogen, C1-C6alkyl or -OR 11 wherein said "C1-C6alkyl" each independently is unsubstituted or substituted with halogen.

5. A heterocyclic substituted aromatic compound according to claim 1, characterized in that, R1, R2, R3, R4 independently represent hydrogen, halogen, C1-C6 alkyl or -OR 11 wherein said "C1-C6 alkyl" is independently unsubstituted or substituted with halogen; R5 stands for hydrogen.

6. A heterocyclic substituted aromatic compound according to claim 1, characterized in that, X1 represents hydrogen, C1-C6 alkyl, or C3-C6 cycloalkyl, wherein, The "C1-C6 alkyl" groups are independently unsubstituted or substituted by one, two, or three groups selected from halogens; X2represents .

7. A heterocyclic substituted aromatic compound according to claim 1, characterized in that, W3represents independently for each occurrence hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl or wherein said "C1-C6alkyl", "C2-C6alkenyl" or "C2-C6alkynyl" is each independently unsubstituted or substituted with 1, 2 or 3 radicals selected from halogen, cyano, C3-C6cycloalkyl, aryl, or 1, 2 or 3 radicals selected from halogen, cyano, C3-C6cycloalkyl, aryl, NW4W5 represents which is unsubstituted or substituted by 1, 2 or 3 radicals selected from C1-C6alkyl; X 11 each independently represents a C1-C6alkyl group; X 13 , X 14 each independently represents hydrogen, C1-C6alkoxy, C1-C6alkoxyC1-C6alkyl, C1-C6alkyl, C3-C6cycloalkyl, aryl or heterocyclyl, or the groups CX 13 X 14 together form a 5- to 8-membered saturated carbocyclic ring, wherein said "C1-C6alkyl" is each independently unsubstituted or substituted with halogen, and said "aryl" or "heterocyclyl" is each independently unsubstituted or substituted with 1, 2 or 3 groups selected from C1-C6alkyl.

8. A heterocyclic substituted aromatic compound according to claim 1, characterized in that, W3represents independently for each occurrence hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl or wherein said "C1-C6alkyl", "C2-C6alkenyl" or "C2-C6alkynyl" are each independently unsubstituted or substituted with 1, 2 or 3 radicals selected from halogen, cyano, C3-C6cycloalkyl, aryl, or halogen; said "aryl" is independently unsubstituted or substituted with 1, 2 or 3 radicals selected from halogen; NW4W5 represents which is unsubstituted or substituted by 1, 2 or 3 radicals selected from C1-C6alkyl; X 11 each independently represents a C1-C6alkyl group; X 13 , X 14 each independently represents hydrogen, C1-C6alkoxy, C1-C6alkoxyC1-C3alkyl, C1-C6alkyl, C3-C6cycloalkyl, aryl or heterocyclyl, or a group CX 13 X 14 together form a 5-membered saturated carbocyclic ring, wherein said "C1-C6alkyl" is each independently unsubstituted or substituted with halogen, and said "heterocyclyl" is each independently unsubstituted or substituted with 1, 2 or 3 groups selected from C1-C6alkyl.

9. A heterocyclic substituted aromatic compound according to claim 1, characterized in that, R 11 each independently represents a C1-C6alkyl group, wherein said "C1-C6alkyl" is independently unsubstituted or substituted with halogen.

10. The heterocyclic substituted aromatic compound according to any one of claims 1 to 9, wherein The compound is selected from any one of the following tables: 。 11. A method for preparing a heterocyclic substituted aromatic compound as described in any one of claims 1-10, 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, Y, and Z are defined as in any one of claims 1-10.

12. The method of claim 11, wherein, The reaction is carried out in the presence of a base and a solvent.

13. The method of claim 12, wherein, The base is selected from at least one of nitrogen-containing bases; the solvent is selected from at least one of aromatic hydrocarbons, THF, DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, dioxane, dichloromethane, toluene, or ethyl acetate.

14. A herbicidal composition, characterized by, Including at least one of the heterocyclic substituted aromatic compounds according to any one of claims 1-10 in an effective amount for herbicidal purposes.

15. The herbicide composition according to claim 14, characterized in that, It also includes pharmaceutical additives.

16. A method of controlling weeds, characterized by, The herbicide composition comprising at least one of the heterocyclic-substituted aromatic compounds of any one of claims 1-10 or the herbicide composition of claim 14 or 15 is used on plants or in weedy areas.

17. Use of at least one of the heterocyclic substituted aromatic compounds according to any one of claims 1-10 or the herbicide composition according to claim 14 or 15 in the control of weeds.

18. Use according to claim 17, characterized in that, The heterocyclic-substituted aromatic compounds are used to control weeds in useful crops, which are genetically modified crops or crops treated with genome editing technology.

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