SUBSTITUTED THIAZOLE AROMATIC RING-BASED COMPOUND AND PREPARATION METHOD THEREFOR, HERBICIDAL COMPOSITION AND USE THEREOF

Abstract

A substituted thiazole aromatic ring compound and a preparation method therefor, a herbicidal composition and use thereof. The substituted thiazole aromatic ring compound is as shown in general formula I:

##STR00001##

Wherein, Y represents halogen, halogenated alkyl, cyano, nitro or amino; Q represents

##STR00002##

M represents CH or N; X represents

##STR00003##

X.sub.1 represents O or S; X.sub.2 represents OX.sub.3, SX.sub.3 or N(X.sub.3).sub.2. The compound has excellent herbicidal activity against gramineous weeds, broadleaf weeds, and so on even at low application rates, and has high selectivity for crops.

Claims

1. A substituted thiazole aromatic ring compound, as shown in general formula I: ##STR00672## wherein, Y represents halogen, halogenated alkyl, cyano, nitro or amino; Q represents ##STR00673## Q.sub.1, Q.sub.2, Q.sub.3, Q.sub.4, Q.sub.5 each independently represent O or S; R.sub.1, R.sub.2 each independently represent hydrogen, cyano, alkyl, alkenyl, alkynyl, formylalkyl, cyanoalkyl, amino, aminoalkyl, aminocarbonyl, aminocarbonylalkyl, aminosulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, R.sub.4R.sub.5N—(CO)—NR.sub.3—, ##STR00674##  R.sub.3—S(O).sub.m-(alkyl).sub.n-, R.sub.3—O-(alkyl).sub.n-, R.sub.3—(CO)-(alkyl).sub.n-, R.sub.3—O-(alkyl).sub.n-(CO)—, R.sub.3—(CO)—O-(alkyl).sub.n-, R.sub.3—S—(CO)-(alkyl).sub.n-, R.sub.3—O—(CO)-alkyl- or R.sub.3—O—(CO)—O-alkyl-; wherein, the “alkyl”, “alkenyl” or “alkynyl” is each independently unsubstituted or substituted by halogen; the “amino”, “aminoalkyl”, “aminocarbonyl”, “aminocarbonylalkyl” or “aminosulfonyl” is each independently unsubstituted or substituted with one or two substituents selected from —R.sub.11, —OR.sub.11, —(CO)R.sub.11, —(CO)OR.sub.11, —O(CO)R.sub.11, -alkyl-(CO)OR.sub.11, —(SO.sub.2)R.sub.11, —(SO.sub.2)OR.sub.11, -alkyl-(SO.sub.2)R.sub.11, —(CO)N(R.sub.12).sub.2 or —(SO.sub.2)N(R.sub.12).sub.2; the “cycloalkyl”, “cycloalkylalkyl”, “cycloalkenyl”, “cycloalkenylalkyl”, “heterocyclyl”, “heterocyclylalkyl”, “aryl” or “arylalkyl” is each independently unsubstituted or substituted with at least one substituent selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, halogenated alkyl, halogenated alkenyl, halogenated alkynyl, halogenated cycloalkyl, cycloalkyl substituted with alkyl, —OR.sub.13, —SR.sub.13, —(CO)OR.sub.13, —(SO.sub.2)R.sub.13, —N(R.sub.13).sub.2 or —O-alkyl-(CO)OR.sub.13, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; R.sub.6, R.sub.7 each independently represent hydrogen, alkyl or halogenated alkyl; M represents CH or N; X represents ##STR00675## X.sub.1 represents O or S; X.sub.2 represents OX.sub.3, SX.sub.3 or N(X.sub.3).sub.2; X.sub.3 each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, arylalkyl ##STR00676##  wherein, the “alkyl”, “alkenyl” or “alkynyl” is each independently unsubstituted or substituted with at least one substituent selected from halogen, cyano, nitro, trialkylsilyl, ##STR00677##  the “cycloalkyl”, “cycloalkylalkyl”, “cycloalkenyl”, “cycloalkenylalkyl”, “heterocyclyl”, “heterocyclylalkyl”, “aryl” or “arylalkyl” is each independently unsubstituted or substituted with at least one substituent selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, halogenated alkyl, halogenated alkenyl, halogenated alkynyl, halogenated cycloalkyl, cycloalkyl substituted with alkyl, —OR.sub.13, —SR.sub.13, —(CO)OR.sub.13, —(SO.sub.2)R.sub.13, —N(R.sub.13).sub.2 or —O-alkyl-(CO)OR.sub.13, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; or N(X.sub.3).sub.2 represents unsubstituted or substituted heterocyclyl with nitrogen atom at 1-position; X.sub.11 each independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl or arylalkyl; wherein, the “cycloalkyl”, “cycloalkylalkyl”, “cycloalkenyl”, “cycloalkenylalkyl”, “heterocyclyl”, “heterocyclylalkyl”, “aryl” or “arylalkyl” is each independently unsubstituted or substituted with at least one substituent selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, halogenated alkyl, halogenated alkenyl, halogenated alkynyl, halogenated cycloalkyl, cycloalkyl substituted with alkyl, —OR.sub.13, —SR.sub.13, —(CO)OR.sub.13, —(SO.sub.2)R.sub.13, —N(R.sub.13).sub.2 or —O-alkyl-(CO)OR.sub.13, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; X.sub.12 each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl or arylalkyl; wherein, the “cycloalkyl”, “cycloalkylalkyl”, “cycloalkenyl”, “cycloalkenylalkyl”, “heterocyclyl”, “heterocyclylalkyl”, “aryl” or “arylalkyl” is each independently unsubstituted or substituted with at least one substituent selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, halogenated alkyl, halogenated alkenyl, halogenated alkynyl, halogenated cycloalkyl, cycloalkyl substituted with alkyl, —OR.sub.13, —SR.sub.13, —(CO)OR.sub.13, —(SO.sub.2)R.sub.13, —N(R.sub.13).sub.2 or —O-alkyl-(CO)OR.sub.13, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; X.sub.13, X.sub.14 each independently represent hydrogen, halogen, cyano, alkoxy, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkyl sulfonyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, or the CX.sub.13X.sub.14 group together forms unsubstituted or substituted ring structure, or the NX.sub.13X.sub.14 group together forms unsubstituted or substituted heterocyclyl with nitrogen atom at 1-position; wherein, the “alkyl”, “alkenyl” or “alkynyl” is each independently unsubstituted or substituted by halogen; the “cycloalkyl”, “cycloalkylalkyl”, “cycloalkenyl”, “cycloalkenylalkyl”, “aryl”, “arylalkyl”, “heterocyclyl” or “heterocyclylalkyl” is each independently unsubstituted or substituted with at least one substituent selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, halogenated alkyl, halogenated alkenyl, halogenated alkynyl, halogenated cycloalkyl, cycloalkyl substituted with alkyl, —OR.sub.13, —SR.sub.13, —(CO)OR.sub.13, —(SO.sub.2)R.sub.13, —N(R.sub.13).sub.2 or —O-alkyl-(CO)OR.sub.13, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; R.sub.3, R.sub.4, R.sub.5 each independently represent hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl or arylalkyl; wherein, the “alkyl”, “alkenyl” or “alkynyl” is each independently unsubstituted or substituted by halogen; the “cycloalkyl”, “cycloalkylalkyl”, “cycloalkenyl”, “cycloalkenylalkyl”, “heterocyclyl”, “heterocyclylalkyl”, “aryl” or “arylalkyl” is each independently unsubstituted or substituted with at least one substituent selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, halogenated alkyl, halogenated alkenyl, halogenated alkynyl, halogenated cycloalkyl, cycloalkyl substituted with alkyl, —OR.sub.13, —SR.sub.13, —(CO)OR.sub.13, —(SO.sub.2)R.sub.13, —N(R.sub.13).sub.2 or —O-alkyl-(CO)OR.sub.13, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; R.sub.11 each independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl or benzyl; wherein, the “alkyl”, “alkenyl” or “alkynyl” is each independently unsubstituted or substituted by halogen; the “phenyl” or “benzyl” is each independently unsubstituted or substituted with at least one substituent selected from halogen, cyano, nitro, alkyl, halogenated alkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or halogenated alkoxy; R.sub.12 each independently represents hydrogen, alkyl, alkenyl, alkynyl, alkoxy, alkylsulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl; or the group N(R.sub.12).sub.2 of —(CO)N(R.sub.12).sub.2 or —(SO.sub.2)N(R.sub.12).sub.2 each independently represents unsubstituted or substituted heterocyclyl with nitrogen atom at 1-position; R.sub.13 each independently represents hydrogen, alkyl, halogenated alkyl, phenyl or phenyl substituted with at least one substituent selected from halogen, cyano, nitro, alkyl, halogenated alkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or halogenated alkoxy; m represents 0, 1 or 2; n independently represents 0 or 1.

2. The substituted thiazole aromatic ring compound according to claim 1, which is characterized in that, Y represents halogen, halogenated C1-C8 alkyl, cyano, nitro or amino; R.sub.1, R.sub.2 each independently represent hydrogen, cyano, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, formyl C1-C8 alkyl, cyano C1-C8 alkyl, amino, amino C1-C8 alkyl, aminocarbonyl, aminocarbonyl C1-C8 alkyl, aminosulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, R.sub.4R.sub.5N—(CO)—NR.sub.3—, ##STR00678##  R.sub.3—S(O).sub.m—(C1-C8 alkyl).sub.n-, R.sub.3—O—(C1-C8 alkyl).sub.n-, R.sub.3—(CO)—(C1-C8 alkyl).sub.n-, R.sub.3—O—(C1-C8 alkyl).sub.n-(CO)—, R.sub.3—(CO)—O—(C1-C8 alkyl).sub.n-, R.sub.3—S—(CO)—(C1-C8 alkyl).sub.n-, R.sub.3—O—(CO)—(C1-C8 alkyl)- or R.sub.3—O—(CO)—O—(C1-C8 alkyl)-; wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl” or “C2-C8 alkynyl” is each independently unsubstituted or substituted by halogen; the “amino”, “amino C1-C8 alkyl”, “aminocarbonyl”, “aminocarbonyl C1-C8 alkyl” or “aminosulfonyl” is each independently unsubstituted or substituted with one or two substituents selected from —R.sub.11, —OR.sub.11, —(CO)R.sub.11, —(CO)OR.sub.11, —O(CO)R.sub.11, —(C1-C8 alkyl)-(CO)OR.sub.11, —(SO.sub.2)R.sub.11, —(SO.sub.2)OR.sub.11, —(C1-C8 alkyl)-(SO.sub.2)R.sub.11, —(CO)N(R.sub.12).sub.2 or —(SO.sub.2)N(R.sub.12).sub.2; the “C3-C8 cycloalkyl”, “C3-C8 cycloalkyl C1-C8 alkyl”, “C3-C8 cycloalkenyl”, “C3-C8 cycloalkenyl C1-C8 alkyl”, “heterocyclyl”, “heterocyclyl C1-C8 alkyl”, “aryl” or “aryl C1-C8 alkyl” is each independently unsubstituted or substituted with at least one substituent selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, —OR.sub.13, —SR.sub.13, —(CO)OR.sub.13, —(SO.sub.2)R.sub.13, —N(R.sub.13).sub.2 or —O—(C1-C8 alkyl)-(CO)OR.sub.13, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; R.sub.6, R.sub.7 each independently represent hydrogen, C1-C8 alkyl or halogenated C1-C8 alkyl; X.sub.3 each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, ##STR00679##  wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl” or “C2-C8 alkynyl” is each independently unsubstituted or substituted with at least one substituent selected from halogen, cyano, nitro, tri-C1-C8 alkylsilyl, ##STR00680##  the “C3-C8 cycloalkyl”, “C3-C8 cycloalkyl C1-C8 alkyl”, “C3-C8 cycloalkenyl”, “C3-C8 cycloalkenyl C1-C8 alkyl”, “heterocyclyl”, “heterocyclyl C1-C8 alkyl”, “aryl” or “aryl C1-C8 alkyl” is each independently unsubstituted or substituted with at least one substituent selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, —OR.sub.13, —SR.sub.13, —(CO)OR.sub.13, —(SO.sub.2)R.sub.13, —N(R.sub.13).sub.2 or —O—(C1-C8 alkyl)-(CO)OR.sub.13, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; or N(X.sub.3).sub.2 represents ##STR00681##  which is unsubstituted or substituted with at least one substituent selected from C1-C8 alkyl; X.sub.11 each independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl or aryl C1-C8 alkyl; wherein, the “C3-C8 cycloalkyl”, “C3-C8 cycloalkyl C1-C8 alkyl”, “C3-C8 cycloalkenyl”, “C3-C8 cycloalkenyl C1-C8 alkyl”, “heterocyclyl”, “heterocyclyl C1-C8 alkyl”, “aryl” or “aryl C1-C8 alkyl” is each independently unsubstituted or substituted with at least one substituent selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, —OR.sub.13, —SR.sub.13, —(CO)OR.sub.13, —(SO.sub.2)R.sub.13, —N(R.sub.13).sub.2 or —O—(C1-C8 alkyl)-(CO)OR.sub.13, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; X.sub.12 each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl or aryl C1-C8 alkyl; wherein, the “C3-C8 cycloalkyl”, “C3-C8 cycloalkyl C1-C8 alkyl”, “C3-C8 cycloalkenyl”, “C3-C8 cycloalkenyl C1-C8 alkyl”, “heterocyclyl”, “heterocyclyl C1-C8 alkyl”, “aryl” or “aryl C1-C8 alkyl” is each independently unsubstituted or substituted with at least one substituent selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, —OR.sub.13, —SR.sub.13, —(CO)OR.sub.13, —(SO.sub.2)R.sub.13, —N(R.sub.13).sub.2 or —O—(C1-C8 alkyl)-(CO)OR.sub.13, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; X.sub.13, X.sub.14 each independently represent hydrogen, halogen, cyano, C1-C8 alkoxy, C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkylsulfonyl, 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, heterocyclyl or heterocyclyl C1-C8 alkyl, or the CX.sub.13X.sub.14 group together forms 5- to 8-membered carbocyclyl or oxygen-, sulfur- or nitrogen-containing heterocyclyl, or the NX.sub.13X.sub.14 group together forms heterocyclyl ##STR00682##  with nitrogen atom at 1-position; wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl” or “C2-C8 alkynyl” is each independently unsubstituted or substituted by halogen; the “C3-C8 cycloalkyl”, “C3-C8 cycloalkyl C1-C8 alkyl”, “C3-C8 cycloalkenyl”, “C3-C8 cycloalkenyl C1-C8 alkyl”, “aryl”, “aryl C1-C8 alkyl”, “heterocyclyl” or “heterocyclyl C1-C8 alkyl” is each independently unsubstituted or substituted with at least one substituent selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, —OR.sub.13, —SR.sub.13, —(CO)OR.sub.13, —(SO.sub.2)R.sub.13, —N(R.sub.13).sub.2 or —O—(C1-C8 alkyl)-(CO)OR.sub.13, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; the “5- to 8-membered carbocyclyl or oxygen-, sulfur- or nitrogen-containing heterocyclyl” is unsubstituted or substituted with at least one substituent selected from C1-C8 alkyl, C1-C8 alkoxycarbonyl or benzyl, or forms a fused ring structure with aryl or heterocyclyl; the ##STR00683##  is unsubstituted or substituted with at least one substituent selected from C1-C8 alkyl; R.sub.3, R.sub.4, R.sub.5 each independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl or aryl C1-C8 alkyl; wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl” or “C2-C8 alkynyl” is each independently unsubstituted or substituted by halogen; the “C3-C8 cycloalkyl”, “C3-C8 cycloalkyl C1-C8 alkyl”, “C3-C8 cycloalkenyl”, “C3-C8 cycloalkenyl C1-C8 alkyl”, “heterocyclyl”, “heterocyclyl C1-C8 alkyl”, “aryl” or “aryl C1-C8 alkyl” is each independently unsubstituted or substituted with at least one substituent selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, halogenated C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, —OR.sub.13, —SR.sub.13, —(CO)OR.sub.13, —(SO.sub.2)R.sub.13, —N(R.sub.13).sub.2 or —O—(C1-C8 alkyl)-(CO)OR.sub.13, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; R.sub.11 each independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, phenyl or benzyl; wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl” or “C2-C8 alkynyl” is each independently unsubstituted or substituted by halogen; the “phenyl” or “benzyl” is each independently unsubstituted or substituted with at least one substituent selected from halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halogenated C1-C8 alkoxy; R.sub.12 each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylsulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl or C3-C8 cycloalkenyl C1-C8 alkyl; or the N(R.sub.12).sub.2 group of —(CO)N(R.sub.12).sub.2 or —(SO.sub.2)N(R.sub.12).sub.2 each independently represents ##STR00684##  which is unsubstituted or substituted with at least one substituent selected from C1-C8 alkyl; R.sub.13 each independently represents hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, phenyl or phenyl substituted with at least one substituent selected from halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halogenated C1-C8 alkoxy.

3. The substituted thiazole aromatic ring compound according to claim 1, which is characterized in that, Y represents halogen, halogenated C1-C6 alkyl, cyano, nitro or amino; R.sub.1, R.sub.2 each independently represent hydrogen, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, formyl C1-C6 alkyl, cyano C1-C6 alkyl, amino, amino C1-C6 alkyl, aminocarbonyl, aminocarbonyl C1-C6 alkyl, aminosulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, R.sub.4R.sub.5N—(CO)—NR.sub.3—, ##STR00685##  R.sub.3—S(O).sub.m—(C1-C6 alkyl).sub.n-, R.sub.3—O—(C1-C6 alkyl).sub.n-, R.sub.3—(CO)—(C1-C6 alkyl).sub.n-, R.sub.3—O—(C1-C6 alkyl).sub.n-(CO)—, R.sub.3—(CO)—O—(C1-C6 alkyl).sub.n-, R.sub.3—S—(CO)—(C1-C6 alkyl).sub.n-, R.sub.3—O—(CO)—(C1-C6 alkyl)- or R.sub.3—O—(CO)—O—(C1-C6 alkyl)-; wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” or “C2-C6 alkynyl” is each independently unsubstituted or substituted by halogen; the “amino”, “amino C1-C6 alkyl”, “aminocarbonyl”, “aminocarbonyl C1-C6 alkyl” or “aminosulfonyl” is each independently unsubstituted or substituted with one or two substituents selected from —R.sub.11, —OR.sub.11, —(CO)R.sub.11, —(CO)OR.sub.11, —O(CO)R.sub.11, —(C1-C6 alkyl)-(CO)OR.sub.11, —(SO.sub.2)R.sub.11, —(SO.sub.2)OR.sub.11, —(C1-C6 alkyl)-(SO.sub.2)R.sub.11, —(CO)N(R.sub.12).sub.2 or —(SO.sub.2)N(R.sub.12).sub.2; the “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 each independently unsubstituted or substituted with one, two or three substituents 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.sub.13, —SR.sub.13, —(CO)OR.sub.13, —(SO.sub.2)R.sub.13, —N(R.sub.13).sub.2 or —O—(C1-C6 alkyl)-(CO)OR.sub.13, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; R.sub.6, R.sub.7 each independently represent hydrogen, C1-C6 alkyl or halogenated C1-C6 alkyl; X.sub.3 each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, ##STR00686##  wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” or “C2-C6 alkynyl” is each independently unsubstituted or substituted with one, two or three substituents selected from halogen, cyano, nitro, tri-C1-C6 alkylsilyl ##STR00687##  the “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 each independently unsubstituted or substituted with one, two or three substituents 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.sub.13, —SR.sub.13, —(CO)OR.sub.13, —(SO.sub.2)R.sub.13, —N(R.sub.13).sub.2 or —O—(C1-C6 alkyl)-(CO)OR.sub.13, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; or N(X.sub.3).sub.2 represents ##STR00688##  which is unsubstituted or substituted with one, two or three substituents selected from C1-C6 alkyl; X.sub.11 each 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, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl or aryl C1-C6 alkyl; wherein, the “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 each independently unsubstituted or substituted with one, two or three substituents 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.sub.13, —SR.sub.13, —(CO)OR.sub.13, —(SO.sub.2)R.sub.13, —N(R.sub.13).sub.2 or —O—(C1-C6 alkyl)-(CO)OR.sub.13, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; X.sub.12 each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl or aryl C1-C6 alkyl; wherein, the “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 each independently unsubstituted or substituted with one, two or three substituents 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.sub.13, —SR.sub.13, —(CO)OR.sub.13, —(SO.sub.2)R.sub.13, —N(R.sub.13).sub.2 or —O—(C1-C6 alkyl)-(CO)OR.sub.13, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; X.sub.13, X.sub.14 each independently represent hydrogen, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfonyl, 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, heterocyclyl or heterocyclyl C1-C6 alkyl, or the CX.sub.13X.sub.14 group together forms 5- to 8-membered saturated carbocyclyl, ##STR00689##  or the NX.sub.13X.sub.14 group together forms ##STR00690##  wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” or “C2-C6 alkynyl” is each independently unsubstituted or substituted by halogen; the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C6 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C6 alkyl”, “aryl”, “aryl C1-C6 alkyl”, “heterocyclyl” or “heterocyclyl C1-C6 alkyl” is each independently unsubstituted or substituted with one, two or three substituents 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.sub.13, —SR.sub.13, —(CO)OR.sub.13, —(SO.sub.2)R.sub.13, —N(R.sub.13).sub.2 or —O—(C1-C6 alkyl)-(CO)OR.sub.13, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; the “5- to 8-membered saturated carbocyclyl, ##STR00691##  is unsubstituted or substituted with one, two or three substituents selected from C1-C6 alkyl, C1-C6 alkoxycarbonyl or benzyl, or forms a fused ring structure with aryl or heterocyclyl; the ##STR00692##  is unsubstituted or substituted with one, two or three substituents selected from C1-C6 alkyl; R.sub.3, R.sub.4, R.sub.5 each independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl or aryl C1-C6 alkyl; wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” or “C2-C6 alkynyl” is each independently unsubstituted or substituted by halogen; the “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 each independently unsubstituted or substituted with one, two or three substituents 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.sub.13, —SR.sub.13, —(CO)OR.sub.13, —(SO.sub.2)R.sub.13, —N(R.sub.13).sub.2 or —O—(C1-C6 alkyl)-(CO)OR.sub.13, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; R.sub.11 each 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, phenyl or benzyl; wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” or “C2-C6 alkynyl” is each independently unsubstituted or substituted by halogen; the “phenyl” or “benzyl” is each independently unsubstituted or substituted with one, two or three substituents selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy; R.sub.12 each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl or C3-C6 cycloalkenyl C1-C6 alkyl; or the N(R.sub.12).sub.2 group of —(CO)N(R.sub.12).sub.2 or —(SO.sub.2)N(R.sub.12).sub.2 each independently represents ##STR00693##  which is unsubstituted or substituted with one, two or three substituents selected from C1-C6 alkyl; R.sub.13 each independently represents hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, phenyl or phenyl substituted with one, two or three substituents selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy.

4. The substituted thiazole aromatic ring compound according to claim 1, which is characterized in that, X.sub.3 each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclyl, heterocyclyl C1-C3 alkyl, aryl, aryl C1-C3 alkyl, ##STR00694##  wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” or “C2-C6 alkynyl” is each independently unsubstituted or substituted with one, two or three substituents selected from halogen, cyano, nitro, tri-C1-C6 alkylsilyl, ##STR00695##  the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C3 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C3 alkyl”, “heterocyclyl”, “heterocyclyl C1-C3 alkyl”, “aryl” or “aryl C1-C3 alkyl” is each independently unsubstituted or substituted with one, two or three substituents 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.sub.13, —SR.sub.13, —(CO)OR.sub.13, —(SO.sub.2)R.sub.13, —N(R.sub.13).sub.2 or —O—(C1-C3 alkyl)-(CO)OR.sub.13, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; or N(X.sub.3).sub.2 represents ##STR00696##  which is unsubstituted or substituted with one, two or three substituents selected from C1-C6 alkyl; X.sub.11 each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclyl, heterocyclyl C1-C3 alkyl, aryl or aryl C1-C3 alkyl; wherein, the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C3 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C3 alkyl”, “heterocyclyl”, “heterocyclyl C1-C3 alkyl”, “aryl” or “aryl C1-C3 alkyl” is each independently unsubstituted or substituted with one, two or three substituents 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.sub.13, —SR.sub.13, —(CO)OR.sub.13, —(SO.sub.2)R.sub.13, —N(R.sub.13).sub.2 or —O—(C1-C3 alkyl)-(CO)OR.sub.13, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; X.sub.12 each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclyl, heterocyclyl C1-C3 alkyl, aryl or aryl C1-C3 alkyl; wherein, the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C3 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C3 alkyl”, “heterocyclyl”, “heterocyclyl C1-C3 alkyl”, “aryl” or “aryl C1-C3 alkyl” is each independently unsubstituted or substituted with one, two or three substituents 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.sub.13, —SR.sub.13, —(CO)OR.sub.13, —(SO.sub.2)R.sub.13, —N(R.sub.13).sub.2 or —O—(C1-C3 alkyl)-(CO)OR.sub.13, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; X.sub.13, X.sub.14 each independently represent hydrogen, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxy C1-C3 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfonyl, 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, heterocyclyl or heterocyclyl C1-C3 alkyl, or the CX.sub.13X.sub.14 group together forms 5- to 8-membered saturated carbocyclyl, ##STR00697##  or the NX.sub.13X.sub.14 group together forms ##STR00698##  wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” or “C2-C6 alkynyl” is each independently unsubstituted or substituted by halogen; the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C3 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C3 alkyl”, “aryl”, “aryl C1-C3 alkyl”, “heterocyclyl” or “heterocyclyl C1-C3 alkyl” is each independently unsubstituted or substituted with one, two or three substituents 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.sub.13, —SR.sub.13, —(CO)OR.sub.13, —(SO.sub.2)R.sub.13, —N(R.sub.13).sub.2 or —O—(C1-C3 alkyl)-(CO)OR.sub.13, or two adjacent carbon atoms on the ring together with unsubstituted or halogen-substituted —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; the “5- to 8-membered saturated carbocyclyl, ##STR00699##  is unsubstituted or substituted with one, two or three substituents selected from C1-C6 alkyl, C1-C6 alkoxycarbonyl or benzyl, or forms a fused ring structure with phenyl or thienyl; the ##STR00700##  is unsubstituted or substituted with one, two or three substituents selected from C1-C6 alkyl; R.sub.13 each independently represents hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, phenyl or phenyl substituted with one, two or three substituents selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy.

5. The substituted thiazole aromatic ring compound according to claim 1, which is characterized in that, Y represents chlorine; R.sub.1, R.sub.2 each independently represent C1-C6 alkyl; R.sub.6 represents C1-C6 alkyl; R.sub.7 represents halogenated C1-C6 alkyl; X.sub.1 represents O; X.sub.2 represents OX.sub.3; X.sub.3 each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, ##STR00701##  benzyl or ##STR00702##  wherein, the “C1-C6 alkyl” is each independently unsubstituted or substituted with one, two or three substituents selected from ##STR00703## X.sub.12 each independently represents C1-C6 alkyl; X.sub.13, X.sub.14 each independently represent C1-C6 alkoxy C1-C3 alkyl or C1-C6 alkyl; preferably, Q represents ##STR00704##  further preferably, it is selected from any one of the following compounds: ##STR00705## ##STR00706## ##STR00707## ##STR00708##

6. A compound as shown in general formula II: ##STR00709## wherein, the substituents Q, Y and M are defined according to claim 1.

7. A method for preparing the substituted thiazole aromatic ring compound according to claim 1, which is characterized by comprising the following steps: subjecting a compound as shown in general formula II and a compound as shown in general formula III to borylation reaction to obtain a compound as shown in general formula I, with the chemical reaction equation shown as follows: ##STR00710## wherein, Hal represents halogen, other substituents Q, Y, X and M are defined according to claim 1; preferably, the reaction is carried out in the presence of a catalyst, a base and a solvent; further preferably, the catalyst is Pd(dppf)Cl.sub.2CH.sub.2Cl.sub.2, Pd(dba).sub.2, Pd.sub.2(dba).sub.3, Pd(PPh.sub.3).sub.4, PdCl.sub.2, Pd(OAc).sub.2, Pd(dppf)Cl.sub.2, Pd(PPh.sub.3).sub.2Cl.sub.2 or Ni(dppf)Cl.sub.2, the base is one or more selected from the group consisting of K.sub.2CO.sub.3, K.sub.3PO.sub.4, Na.sub.2CO.sub.3, CsF, Cs.sub.2CO.sub.3, t-Bu-Na and NaOH, and the solvent is DMSO, DMF, DMA, toluene, acetonitrile, 1,4-dioxane, 1,4-dioxane/water, toluene/ethanol/water or acetonitrile/water system.

8. An herbicidal composition, which is characterized in that it comprises at least one of the substituted thiazole aromatic ring compound according to claim 1 in a herbicidally effective amount, preferably, further comprises a formulation auxiliary.

9. A method of controlling a weed, which is characterized in that it comprises applying at least one of the substituted thiazole aromatic ring compound according to claim 1 in a herbicidally effective amount on a plant or a weed area.

10. (canceled)

11. A method of controlling a weed, which is characterized in that it comprises applying at least one of the herbicidal composition according to claim 8 in a herbicidally effective amount on a plant or a weed area.

12. A method of controlling a weed in a useful crop, which is characterized in that it comprises applying at least one of the substituted thiazole aromatic ring compound according to claim 1 in a herbicidally effective amount on a plant or a weed area, and the useful crop is a transgenic crop or a crop treated by genome editing technique.

13. A method of controlling a weed in a useful crop, which is characterized in that it comprises applying at least one of the herbicidal composition according to claim 8 in a herbicidally effective amount on a plant or a weed area, and the useful crop is a transgenic crop or a crop treated by genome editing technique.

Description

SPECIFIC MODE FOR CARRYING OUT THE INVENTION

[0122] The following embodiments are used to illustrate the present invention in detail and should not be taken as any limit to the present invention. The scope of the invention would be explained through the Claims.

[0123] In view of economics and variety of a compound, we preferably synthesized several compounds, part of which are listed in the following Table 1. The structure and information of a certain compound are shown in Table 1. The compounds in Table 1 are listed for further explication of the present invention, other than any limit therefor. The subject of the present invention should not be interpreted by those skilled in the art as being limited to the following compounds.

TABLE-US-00001 TABLE 1 Structures and .sup.1H NMR data of compounds □-1 [00049] NO. Q X Y M .sup.1H NMR 1-1 [00050] [00051] Cl CH 1-2 [00052] [00053] Cl CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.65 (d, J = 1.5 Hz, 1H), 8.58 (d, J = 7.5 Hz, 1H), 8.05 (d, J = 9.0 Hz, 1H), 6.63 (s, 1H), 4.44-4.32 (m, 2H), 3.44 (s, 3H), 1.36 (td, J = 7.0, 1.4 Hz, 3H). 1-3 [00054] [00055] Cl CH 1-4 [00056] [00057] Cl CH 1-5 [00058] [00059] Cl CH 1-6 [00060] [00061] Cl CH 1-7 [00062] [00063] Cl CH 1-8 [00064] [00065] Cl CH 1-9 [00066] [00067] Cl CH 1-10 [00068] [00069] Cl CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.69 (s, 1H), 8.58 (d, J = 8.0 Hz, 1H), 8.05 (d, J = 9.5 Hz, 1H), 6.63 (s, 1H), 6.10-6.03 (m, 1H), 5.48-5.46 (m, 1H), 5.34-5.31 (m, 1H), 4.88-4.86 (m, 2H), 3.44 (s, 3H). 1-11 [00070] [00071] Cl CH 1-12 [00072] [00073] Cl CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.72 (s, 1H), 8.59 (d, J = 8.0 Hz, 1H), 8.06 (d, J = 9.5 Hz, 1H), 6.63 (s, 1H), 5.03 (d, J = 2.5 Hz, 2H), 3.72 (t, J = 2.5 Hz, 1H), 3.44 (s, 3H). 1-13 [00074] [00075] Cl CH 1-14 [00076] [00077] Cl CH 1-15 [00078] [00079] Cl CH 1-16 [00080] [00081] Cl CH 1-17 [00082] [00083] Cl CH 1-18 [00084] [00085] Cl CH 1-19 [00086] [00087] Cl CH 1-20 [00088] [00089] Cl CH 1-21 [00090] [00091] Cl CH 1-22 [00092] [00093] Cl CH 1-23 [00094] [00095] Cl CH 1-24 [00096] [00097] Cl CH 1-25 [00098] [00099] Cl CH 1-26 [00100] [00101] Cl CH 1-27 [00102] [00103] Cl CH 1-28 [00104] [00105] Cl CH 1-29 [00106] [00107] Cl CH 1-30 [00108] [00109] Cl CH 1-31 [00110] [00111] Cl CH 1-32 [00112] [00113] Cl CH 1-33 [00114] [00115] Cl CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.66 (s, 1H), 8.57 (d, J = 8.0 Hz, 1H), 8.06 (d, J = 9.5 Hz, 1H), 6.64 (s, 1H), 4.20-4.15 (m, 1H), 3.84-3.78 (m, 1H), 3.75 (t, J = 6.0 Hz, 2H), 3.73-3.67 (m, 1H), 3.44 (s, 3H), 2.05-1.99 (m, 1H), 1.95-1.86 (m, 2H), 1.71-1.64 (m, 1H). 1-34 [00116] [00117] Cl CH 1-35 [00118] [00119] Cl CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.70 (s, 1H), 8.57 (d, J = 8.0 Hz, 1H), 8.05 (d, J = 9.5 Hz, 1H), 7.51 (d, J = 7.5 Hz, 2H), 7.43-7.41 (m, 3H), 6.63 (s, 1H), 5.42 (s, 2H), 3.44 (s, 3H). 1-36 [00120] [00121] Cl CH 1-37 [00122] [00123] Cl CH 1-38 [00124] [00125] Cl CH 1-39 [00126] [00127] Cl CH 1-40 [00128] [00129] Cl CH 1-41 [00130] [00131] Cl CH 1-42 [00132] [00133] Cl CH 1-43 [00134] [00135] Cl CH 1-44 [00136] [00137] Cl CH 1-45 [00138] [00139] Cl CH 1-46 [00140] [00141] Cl CH 1-47 [00142] [00143] Cl CH 1-48 [00144] [00145] Cl CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.74 (s, 1H), 8.60 (d, J = 7.5 Hz, 1H), 8.07 (d, J = 9.5 Hz, 1H), 6.64 (s, 1H), 5.37 (q, J = 7.0 Hz, 1H), 3.74 (s, 3H), 3.44 (s, 3H), 1.58 (d, J = 7.0 Hz, 3H) 1-49 [00146] [00147] Cl CH 1-50 [00148] [00149] Cl CH 1-51 [00150] [00151] Cl CH 1-52 [00152] [00153] Cl CH 1-53 [00154] [00155] Cl CH 1-54 [00156] [00157] Cl CH 1-55 [00158] [00159] Cl CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.77 (s, 1H), 8.57 (d, J = 8.0 Hz, 1H), 8.06 (d, J = 9.5 Hz, 1H), 6.64 (s, 1H), 3.44 (s, 3H), 2.13 (s, 3H), 2.07 (s, 3H) 1-56 [00160] [00161] Cl CH 1-57 [00162] [00163] Cl CH 1-58 [00164] [00165] Cl CH 1-59 [00166] [00167] Cl CH 1-60 [00168] [00169] Cl CH 1-61 [00170] [00171] Cl CH 1-62 [00172] [00173] Cl CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.81 (s, 1H), 8.59 (d, J = 8.0 Hz, 1H), 8.07 (d, J = 9.5 Hz, 1H), 6.64 (s, 1H), 4.15 (s, 2H), 3.45 (s, 3H), 3.33 (s, 3H), 2.15 (s, 3H). 1-63 [00174] [00175] Cl CH 1-64 [00176] [00177] Cl CH 1-65 [00178] [00179] Cl CH 1-66 [00180] [00181] Cl CH 1-67 [00182] [00183] Cl CH 1-68 [00184] [00185] Cl CH 1-69 [00186] [00187] Cl CH 1-70 [00188] [00189] Cl CH 1-71 [00190] [00191] Cl CH 1-72 [00192] [00193] Cl CH 1-73 [00194] [00195] Cl CH 1-74 [00196] [00197] Cl CH 1-75 [00198] [00199] Cl CH 1-76 [00200] [00201] Cl CH 1-77 [00202] [00203] Cl CH 1-78 [00204] [00205] Cl CH 1-79 [00206] [00207] Cl CH 1-80 [00208] [00209] Cl CH 1-81 [00210] [00211] Cl CH 1-82 [00212] [00213] Cl CH 1-83 [00214] [00215] Cl CH 1-84 [00216] [00217] Cl CH 1-85 [00218] [00219] Cl CH 1-86 [00220] [00221] Cl CH 1-87 [00222] [00223] Cl CH 1-88 [00224] [00225] Cl CH 1-89 [00226] [00227] Cl CH 1-90 [00228] [00229] Cl CH 1-91 [00230] [00231] Cl CH 1-92 [00232] [00233] Cl CH 1-93 [00234] [00235] Cl CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.47 (d, J = 8.0 Hz, 1H), 8.36 (s, 1H), 8.04-7.95 (m, 2H), 6.62 (s, 1H), 3.95-3.90 (m, 1H), 3.42 (s, 3H), 2.44 (s, 3H), 1.04 (d, J = 7.0 Hz, 6H). 1-94 [00236] [00237] Cl CH 1-95 [00238] [00239] Cl CH 1-96 [00240] [00241] Cl CH 1-97 [00242] [00243] Cl CH 1-98 [00244] [00245] Cl CH 1-99 [00246] [00247] Cl CH 1-100 [00248] [00249] Cl CH 1-101 [00250] [00251] Cl CH 1-102 [00252] [00253] Cl CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.80 (d, J = 8.0 Hz, 1H), 8.68 (s, 1H), 8.22 (d, J = 9.0 Hz, 1H), 6.98 (s, 1H), 4.39 (q, J = 7.0 Hz, 2H), 3.36 (s, 3H), 1.35 (t, J = 7.0 Hz, 3H). 1-103 [00254] [00255] Cl CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.65 (s, 1H), 8.59 (d, J = 7.5 Hz, 1H), 8.06 (d, J = 9.0 Hz, 1H), 7.12 (s, 1H), 4.38 (q, J = 7.0 Hz, 2H), 3.43 (s, 3H), 1.35 (t, J = 7.0 Hz, 3H). 1-104 [00256] [00257] Cl CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.82 (d, J = 7.5 Hz, 1H), 8.68 (s, 1H), 8.24 (d, J = 9.0 Hz, 1H), 7.65 (s, 1H), 4.39 (q, J = 7.0 Hz, 2H), 2.54 (s, 3H), 1.36 (t, J = 7.0 Hz, 3H). 1-105 [00258] [00259] Cl CH 1-106 [00260] [00261] Cl CH 1-107 [00262] [00263] Cl N .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.65 (s, 1H), 8.08 (d, J = 7.5 Hz, 1H), 6.63 (s, 1H), 4.44-4.32 (m, 2H), 3.44 (s, 3H), 1.38-1.31 (m, 3H). 1-108 [00264] [00265] Br CH 1-109 [00266] [00267] CF.sub.3 CH 1-110 [00268] [00269] CN CH 1-111 [00270] [00271] NO.sub.2 CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.49 (d, J = 9.0 Hz, 1H), 8.03 (d, J = 6.0 Hz, 1H), 7.98 (s, 1H), 6.68 (s, 1H), 4.30 (q, J = 7.0 Hz, 2H), 3.42 (s, 3H), 1.28 (t, J = 7.0 Hz, 3H). 1-112 [00272] [00273] NH.sub.2 CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.02 (d, J = 6.0 Hz, 1H), 7.98 (s, 1H), 6.80 (d, J = 9.0 Hz, 1H), 6.68 (s, 1H), 4.30 (q, J = 7.0 Hz, 2H), 3.42 (s, 3H), 1.28 (t, J = 7.0 Hz, 3H). 1-113 [00274] [00275] Cl CH .sup.1H NMR (500 MHz, DMSO) δ 8.69 (d, J = 7.5 Hz, 1H), 8.66 (s, 1H), 8.07 (d, J = 9.0 Hz, 1H), 4.38 (q, J = 7.0 Hz, 2H), 3.65 (s, 6H), 1.35 (t, J = 7.0 Hz, 3H). 1-114 [00276] [00277] Cl CH 1-115 [00278] [00279] Cl CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.72 (s, 1H), 8.58 (d, J = 7.5 Hz, 1H), 8.05 (d, J = 9.0 Hz, 1H), 4.38 (q, J = 7.0 Hz, 2H), 3.65 (s, 3H), 3.52 (s, 3H), 1.36 (t, J = 7.0 Hz, 3H). 1-116 [00280] [00281] Cl CH 1-117 [00282] [00283] Cl CH 1-118 [00284] [00285] Br CH 1-119 [00286] [00287] CF.sub.3 CH 1-120 [00288] [00289] CN CH 1-121 [00290] [00291] NO.sub.2 CH 1-122 [00292] [00293] NH.sub.2 CH 1-123 [00294] [00295] Cl N .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.72 (s, 1H), 8.18 (d, J = 7.5 Hz, 1H), 4.44-4.32 (m, 2H), 3.65 (s, 3H), 3.52 (s, 3H), 1.36 (t, J = 7.0 Hz, 3H). 1-124 [00296] [00297] CN N 1-125 [00298] [00299] Cl CH 1-126 [00300] [00301] Cl CH 1-127 [00302] [00303] Cl CH 1-128 [00304] [00305] Cl CH 1-129 [00306] [00307] Cl CH 1-130 [00308] [00309] Cl CH 1-131 [00310] [00311] Cl CH 1-132 [00312] [00313] Cl CH 1-133 [00314] [00315] Cl CH 1-134 [00316] [00317] Cl CH 1-135 [00318] [00319] Cl CH 1-136 [00320] [00321] Cl CH 1-137 [00322] [00323] Cl CH 1-138 [00324] [00325] Cl CH 1-139 [00326] [00327] Cl CH 1-140 [00328] [00329] Cl CH 1-141 [00330] [00331] Cl CH 1-142 [00332] [00333] Cl CH 1-143 [00334] [00335] Cl CH 1-144 [00336] [00337] Cl CH 1-145 [00338] [00339] Cl CH 1-146 [00340] [00341] Cl CH 1-147 [00342] [00343] Cl CH 1-148 [00344] [00345] Cl CH 1-149 [00346] [00347] Cl CH 1-150 [00348] [00349] Cl CH 1-151 [00350] [00351] Cl CH 1-152 [00352] [00353] Cl CH 1-153 [00354] [00355] Cl CH 1-154 [00356] [00357] Cl CH 1-155 [00358] [00359] Cl CH 1-156 [00360] [00361] Cl CH 1-157 [00362] [00363] Cl CH 1-158 [00364] [00365] Cl CH 1-159 [00366] [00367] Cl CH 1-160 [00368] [00369] Cl CH 1-161 [00370] [00371] Cl CH 1-162 [00372] [00373] Cl CH 1-163 [00374] [00375] Cl CH 1-164 [00376] [00377] Cl CH 1-165 [00378] [00379] Cl CH 1-166 [00380] [00381] Cl CH 1-167 [00382] [00383] Cl CH 1-168 [00384] [00385] Cl CH 1-169 [00386] [00387] Cl CH 1-170 [00388] [00389] Cl CH 1-171 [00390] [00391] Cl CH 1-172 [00392] [00393] Cl CH 1-173 [00394] [00395] Cl CH 1-174 [00396] [00397] Cl CH 1-175 [00398] [00399] Cl CH 1-176 [00400] [00401] Cl CH 1-177 [00402] [00403] Cl CH 1-178 [00404] [00405] Cl CH 1-179 [00406] [00407] Cl CH 1-180 [00408] [00409] Cl CH 1-181 [00410] [00411] Cl CH 1-182 [00412] [00413] Cl CH 1-183 [00414] [00415] Cl CH 1-184 [00416] [00417] Cl CH 1-185 [00418] [00419] Cl CH 1-186 [00420] [00421] Cl CH 1-187 [00422] [00423] Cl CH 1-188 [00424] [00425] Cl CH 1-189 [00426] [00427] Cl CH 1-190 [00428] [00429] Cl CH 1-191 [00430] [00431] Cl CH 1-192 [00432] [00433] Cl CH 1-193 [00434] [00435] Cl CH 1-194 [00436] [00437] Cl CH 1-195 [00438] [00439] Cl CH 1-196 [00440] [00441] Cl CH 1-197 [00442] [00443] Cl CH 1-198 [00444] [00445] Cl CH 1-199 [00446] [00447] Cl CH 1-200 [00448] [00449] Cl CH 1-201 [00450] [00451] Cl CH 1-202 [00452] [00453] Cl CH 1-203 [00454] [00455] Cl CH 1-204 [00456] [00457] Cl CH 1-205 [00458] [00459] Cl CH 1-206 [00460] [00461] Cl CH 1-207 [00462] [00463] Cl CH 1-208 [00464] [00465] Cl CH 1-209 [00466] [00467] Cl CH 1-210 [00468] [00469] Cl CH 1-211 [00470] [00471] Cl CH 1-212 [00472] [00473] Cl CH 1-213 [00474] [00475] Cl CH 1-214 [00476] [00477] Cl CH 1-215 [00478] [00479] Cl CH 1-216 [00480] [00481] Cl CH 1-217 [00482] [00483] Cl CH 1-218 [00484] [00485] Cl CH 1-219 [00486] [00487] Cl CH 1-220 [00488] [00489] Cl CH 1-221 [00490] [00491] Cl CH 1-222 [00492] [00493] Cl CH 1-223 [00494] [00495] Cl CH 1-224 [00496] [00497] Cl CH 1-225 [00498] [00499] Cl CH 1-226 [00500] [00501] Cl CH 1-227 [00502] [00503] Cl CH 1-228 [00504] [00505] Cl CH 1-229 [00506] [00507] Cl CH 1-230 [00508] [00509] Cl CH 1-231 [00510] [00511] Cl CH 1-232 [00512] [00513] Cl CH 1-233 [00514] [00515] Cl CH 1-234 [00516] [00517] Cl CH 1-235 [00518] [00519] Cl CH 1-236 [00520] [00521] Cl CH 1-237 [00522] [00523] Cl CH 1-238 [00524] [00525] Cl CH 1-239 [00526] [00527] Cl CH 1-240 [00528] [00529] Cl CH 1-241 [00530] [00531] Cl CH 1-242 [00532] [00533] Cl CH 1-243 [00534] [00535] Cl CH 1-244 [00536] [00537] Cl CH 1-245 [00538] [00539] Cl CH 1-246 [00540] [00541] Cl CH 1-247 [00542] [00543] Cl CH 1-248 [00544] [00545] Cl CH 1-249 [00546] [00547] Cl CH 1-250 [00548] [00549] Cl CH 1-251 [00550] [00551] Cl CH 1-252 [00552] [00553] Cl CH 1-253 [00554] [00555] Cl CH 1-254 [00556] [00557] Cl CH 1-255 [00558] [00559] Cl CH 1-256 [00560] [00561] Cl N 1-257 [00562] [00563] Cl N 1-258 [00564] [00565] Cl N 1-259 [00566] [00567] Cl N 1-260 [00568] [00569] Cl N 1-261 [00570] [00571] Cl N 1-262 [00572] [00573] Cl N 1-263 [00574] [00575] Cl N 1-264 [00576] [00577] Cl N 1-265 [00578] [00579] Cl N 1-266 [00580] [00581] Cl N 1-267 [00582] [00583] Cl N 1-268 [00584] [00585] Cl N 1-269 [00586] [00587] Cl N 1-270 [00588] [00589] Cl N 1-271 [00590] [00591] Cl N 1-272 [00592] [00593] Cl N 1-273 [00594] [00595] Cl N 1-274 [00596] [00597] Cl N 1-275 [00598] [00599] Cl N 1-276 [00600] [00601] Cl N 1-277 [00602] [00603] CN N 1-278 [00604] [00605] NO.sub.2 N 1-279 [00606] [00607] NH.sub.2 N 1-280 [00608] [00609] Cl N 1-281 [00610] [00611] Cl N 1-282 [00612] [00613] Cl N 1-283 [00614] [00615] Cl N 1-284 [00616] [00617] Cl N 1-285 [00618] [00619] Cl N 1-286 [00620] [00621] Cl N 1-287 [00622] [00623] Cl N 1-288 [00624] [00625] Cl N 1-289 [00626] [00627] Cl N 1-290 [00628] [00629] Cl N 1-291 [00630] [00631] Cl N 1-292 [00632] [00633] Cl N 1-293 [00634] [00635] Cl N 1-294 [00636] [00637] Cl N 1-295 [00638] [00639] Cl N 1-296 [00640] [00641] Cl N 1-297 [00642] [00643] Cl N 1-298 [00644] [00645] Cl N 1-299 [00646] [00647] Cl N 1-300 [00648] [00649] NO.sub.2 N 1-301 [00650] [00651] NH.sub.2 N

[0124] In addition, the present invention also relates to aftermentioned compounds of other general formula, wherein each substituent is defined as shown in Table 1 and the corresponding compounds are numbered from 2-1 to 2-301, 3-1 to 3-301, and so on. For example, compound 2-1 represents Q

##STR00652##

X

[0125] ##STR00653##

Y (Cl), M (CH).

[0126]

TABLE-US-00002 Table No. General Formula 2 [00654]   □-2 3 [00655]   □-3 4 [00656]   □-4 5 [00657]   □-5 6 [00658]   □-6

TABLE-US-00003 TABLE 7 .sup.1H NMR data of certain compounds No. .sup.1H NMR 2-2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.65 (s, 1H), 8.58 (d, J = 8.0 Hz, 1H), 8.06 (d, J = 9.5 Hz, 1H), 6.64 (s, 1H), 4.38 (q, J = 7.0 Hz, 2H), 3.44 (s, 3H), 1.36 (t, J = 7.0 Hz, 3H). 2-113 .sup.1H NMR (500 MHz, DMSO) δ 8.78 (s, 1H), 8.55 (d, J = 7.5 Hz, 1H), 8.04 (d, J = 9.5 Hz, 1H), 4.37 (q, J = 7.0 Hz, 2H), 3.66 (s, 6H), 1.32 (t, J = 7.0 Hz, 3H). 2-115 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.78 (s, 1H), 8.54 (d, J = 7.5 Hz, 1H), 8.03 (d, J = 9.0 Hz, 1H), 4.37 (q, J = 7.0 Hz, 2H), 4.17 (s, 3H), 3.64 (s, 3H), 1.34 (t, J = 7.0 Hz, 3H). 4-1 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.64 (s, 1H), 8.10 (d, J = 8.0 Hz, 1H), 7.93 (d, J = 9.5 Hz, 1H), 6.63 (s, 1H), 3.96 (s, 3H), 3.44 (s, 3H). 4-158 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.65 (s, 1H), 8.21 (d, J = 8.0 Hz, 1H), 7.95 (d, J = 9.5 Hz, 1H), 3.96 (s, 3H), 3.65 (s, 6H). 4-207 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.65 (s, 1H), 8.20 (d, J = 7.5 Hz, 1H), 7.92 (d, J = 9.5 Hz, 1H), 4.16 (s, 3H), 3.96 (s, 3H), 3.64 (s, 3H). 5-2 .sup.1H NMR (500 MHz, DMSO-d6) δ 9.28 (s, 1H), 7.95-7.89 (m, 1H), 7.68 (d, J = 7.6 Hz, 1H), 6.61 (s, 1H), 4.11 (q, J = 7.1 Hz, 2H), 3.42 (s, 3H), 1.05(t, J = 7.0 Hz, 3H). 5-113 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 9.30 (s, 1H), 7.99-7.94 (m, 1H), 7.74 (d, J = 7.5 Hz, 1H), 4.13 (q, J = 7.0 Hz, 2H), 3.64 (s, 6H), 1.33 (t, J = 7.0 Hz, 3H).

[0127] The method for preparing the compound of the invention will be explained in detail in the following program and embodiment. The material is commercial available or prepared through known method reported in the literature or shown in the route. Those skilled in the art should understand that the compound of the invention can also be synthesized by other synthetic route. Although the detailed material and reaction condition in the synthetic route have been explicated in the following text, it is still easy to be replaced by other similar material and condition. Isomer of the compound, for example, that produced with the variation of the preparation method of the present invention is included in the scope of the present invention. In addition, the following preparation method can be further modified according to the disclosures of the present invention by using common chemical method known to those skilled in the art, for example, protection of suitable group in the process of the reaction, etc.

[0128] The following method of application can be used to improve further understanding of the preparation method of the present invention. The specific material, class and condition have been determined to be further explication of the present invention, not to be any limit of the reasonable scope thereof. Reagents of the following synthetic compound showed in the table can either be purchased from the market or easily prepared by those skilled in the art.

[0129] Examples of representative compounds are as follows, the synthesis methods of other compounds are similar, and will not be described in detail here.

[0130] 1. Synthesis of Compound 1-2

[0131] (1) Compound 2-1 (20 g, 105.3 mmol), NCS (14.05 g, 105.3 mmol) and anhydrous acetonitrile (200 mL) were placed in a round bottom flask. The mixture was heated to 35° C. and stirred for 16 hours. After the raw material was completely reacted by HPLC-MS detection, the reaction solution was concentrated to remove acetonitrile. The crude product was extracted with water (200 mL) and ethyl acetate (200 mL×2), and the organic phase was washed once with saturated brine (200 mL), dried and concentrated to produce crude compound 2-2 (24 g, used directly in the next step without purification), as a brown oily substance.

##STR00659##

[0132] (2) Compound 2-2 (24 g, 106.9 mmol), compound a (47.6 g, 160.4 mmol) and anhydrous dichloromethane (200 mL) were placed in a round bottom flask. The mixture was cooled to 0° C. and triethylamine (16.23 g, 160.4 mmol) was slowly dropwise added at a temperature not higher than 10° C. during the process, and then stirred at 0-10° C. for 20 minutes. After the raw material was completely reacted by HPLC-MS detection, the product was directly used in the next step without treatment considering the instability of the compound 2-3.

##STR00660##

[0133] (3) Anhydrous ethanol (240 mL, 10v) was dropped into the above reaction solution of compound 2-3 at a temperature of 0-10° C. The mixture was stirred for 1 hour at room temperature, the principal peak generated in HPLC-MS belonged to the product. The reaction solution was concentrated, and the crude product was extracted with water (200 mL) and dichloromethane (200 mL×2). The organic phase was dried and concentrated, purified by column chromatography to obtain compound 2-4 (20 g, 67.4 mmol, yield 74%), as a yellow solid.

##STR00661##

[0134] (4) Compound 2-4 (20 g, 67.4 mmol), compound b (13.1 g, 70.8 mmol), cesium carbonate (43.95 g, 134.9 mmol) and N,N-dimethylacetamide (200 mL) were placed in a round bottom flask. The mixture was heated to 130° C. and stirred for 16 hours, the raw material was completely reacted by HPLC-MS detection. The reaction solution was cooled to room temperature, and then extracted with ethyl acetate (200 mL×2) and water. The organic phase was dried and concentrated, purified by column chromatography to obtain compound 2-5 (15 g, yield 57%), as a yellow solid.

##STR00662##

[0135] (5) Compound 2-5 (15 g, 38.7 mmol), potassium carbonate (10.7 g, 77.4 mmol) and acetonitrile (150 mL) were placed in a round bottom flask. Iodomethane (16.5 g, 116.1 mmol) was dropwise added at room temperature. The mixture was heated to 80° C. and stirred for 1 hour, the raw material was completely reacted by HPLC-MS detection. The reaction solution was concentrated to remove acetonitrile. The crude product was extracted with ethyl acetate (200 mL×2) and water, and the organic phase was dried and concentrated, then purified by column chromatography to obtain compound 2-6 (15 g, yield 96%), as a yellow solid.

##STR00663##

[0136] (6) Compound 2-6 (15 g, 37.6 mmol), potassium acetate (11 g, 112 mmol), compound c (19.0 g, 74.7 mmol) and dioxane (150 mL) were placed in a round bottom flask. The air was discharged from the reaction flask under the protection of nitrogen and then nitrogen replacement was performed three times. The mixture was added with a catalytic amount of Pd(dppf)Cl.sub.2 (150 mg) under the protection of nitrogen, then subjected to nitrogen replacement for three times, heated to 100° C., reacted for 16 hours, the raw material was completely reacted by HPLC-MS detection. The reaction solution was concentrated, and then purified by column chromatography to obtain compound 2-7 (13 g, yield 77%), as a white solid.

##STR00664##

[0137] (7) Compound 2-7 (1 g, 2.23 mmol), anhydrous potassium carbonate (616 mg, 4.46 mmol), compound d (631 mg, 2.67 mmol) and dioxane (30 mL) were placed in a round bottom flask. The air was discharged from the reaction flask under the protection of nitrogen and then nitrogen replacement was performed three times. The mixture was added with a catalytic amount of Pd(dppf)Cl.sub.2 (30 mg) under the protection of nitrogen, then subjected to nitrogen replacement for three times, and then heated to 65° C. and reacted for 10 hours until the raw material was completely reacted by HPLC-MS detection. The reaction solution was concentrated, and then purified by column chromatography to obtain compound 1-2 (500 mg, 0.3347 mmol, purity 95%, yield 47%), as a white solid.

##STR00665##

[0138] 2. Synthesis of Compound 1-103

[0139] Compound 2 (200 mg, 0.42 mmol), compound e (186.3 mg, 0.46 mmol) and sodium bicarbonate (141 mg, 1.68 mmol) were placed in a 100 ml round bottom single-mouth flask. Toluene was added and well mixed, then subjected to reflux reaction at 110° C. for 12 hours. After the raw material was almost reacted by HPLC-MS detection, the reaction solution was concentrated, and the crude product was purified by column chromatography to obtain compound 1-103 (100 mg, 0.20 mmol, purity 91%, yield 48.4%), as a yellow solid.

##STR00666##

[0140] 3. Synthesis of Compound 1-113

[0141] (1) Compound 2-2 (5 g, 22.3 mmol) and compound 113-1 (3.84 g, 24.5 mmol) were placed in a 100 ml round bottom single-mouth flask. Toluene (50 mL) was added and well mixed, then subjected to reflux reaction at 110° C. for 1 hour. After the raw material was almost reacted by HPLC-MS detection, the reaction solution was concentrated, and the crude product was purified by column chromatography to obtain compound 113-2 (6 g, yield 78%), as a white solid.

##STR00667##

[0142] (2) Compound 113-3 (5.86 g, 26.1 mmol), sodium acetate (714 mg, 8.71 mmol) and N,N-dimethylformamide (20 mL) were placed in a 100 ml round bottom single-mouth flask. The mixture was heated to 60° C., added with compound 113-2 (6 g, 17.4 mmol) at 60° C., and stirred at 60° C. for 1 hour. After the raw material was completely reacted by HPLC-MS detection, the reaction solution was added with water (100 ml), then extracted with ethyl acetate (100 mL×2). The organic phase was washed with saturated brine (100 ml*1), and then concentrated. The crude product was isolated by column chromatography to obtain compound 113-4 (5 g, yield 75%), as a yellow solid.

##STR00668##

[0143] (3) Compound 113-4 (5 g, 13.14 mmol), potassium acetate (3.87 g, 39.4 mmol), compound c (6.67 g, 26.27 mmol) and dioxane (50 mL) were placed in the round bottom flask. The air was discharged from the reaction flask by nitrogen replacement for three times under the protection of nitrogen. The mixture was added with a catalytic amount of Pd(dppf)Cl.sub.2 (50 mg) under the protection of nitrogen, then subjected to nitrogen replacement for three times, heated to 100° C. and reacted for 16 hours. After the raw material was completely reacted by HPLC-MS detection, the reaction solution was concentrated, then purified by column chromatography to obtain compound 113-5 (4 g, yield 71%), as a yellow solid.

##STR00669##

[0144] (4) Compound 113-5 (0.3 g, 0.7 mmol), anhydrous potassium carbonate (194 mg, 1.4 mmol), compound d (199 mg, 0.84 mmol) and dioxane (20 mL) were placed in a round bottom flask. The air was discharged from the reaction flask by nitrogen replacement for three times under the protection of nitrogen. The mixture was added with a catalytic amount of Pd(dppf)Cl.sub.2 (30 mg) under the protection of nitrogen, then subjected to nitrogen replacement for three times, heated to 65° C. and reacted for 10 hours. After the raw material was completely reacted by HPLC-MS detection, the reaction solution was concentrated, and then purified by column chromatography to obtain compound 1-113 (56 g, purity 90%, yield 17%), as a white solid.

##STR00670##

[0145] Biological Activity Evaluation:

[0146] The activity level criteria for plant damage (i.e., growth control rate) are as follows:

[0147] Level 5: growth control rate is above 85%;

[0148] Level 4: growth control rate is greater than or equal to 60% and less than 85%;

[0149] Level 3: growth control rate is greater than or equal to 40% and less than 60%;

[0150] Level 2: growth control rate is greater than or equal to 20% and less than 40%;

[0151] Level 1: growth control rate is greater than or equal to 5% and less than 20%;

[0152] Level 0: growth control rate is less than 5%.

[0153] The above growth control rates are fresh weight control rates.

[0154] Experiment on weeding effect in post-emergence stage:

[0155] Monocotyledonous and dicotyledonous weed seeds (Descurainia sophia, Capsella bursa-pastoris, Abutilon theophrasti, Galium aparine, Stellaria media, Lithospermum arvense, Rorippa indica, Alopecurus aequalis, Alopecurus japonicus, Beckmannia syzigachne, Sclerochloa dura, Conyza Canadensis, Phleum paniculatum, Veronica didyma Tenore, Eleusine indica, Bromus japonicus, Aegilops tauschii, Phalaris arundinacea, Amaranthus retroflexus, Chenopodium album, Commelina communis, Sonchus arvensis, Convolvulus arvensis, Cirsium setosum, Solanum nigrum, Acalypha australis, Digitaria sanguinalis, Echinochloa crusgalli, Setaria viridis, Setaria glauca, Leptochloa chinensis, Monochoria vaginalis, Sagittaria trifolia, Scirpus juncoides, Cyperus rotundus, Cyperus iria, Cyperus difformis, Fimbristylis, Portulaca oleracea, Xanthium sibiricum, Pharbitis nil) and major crop seeds (wheat, corn, rice, soybean, cotton, oilseed rape, millet, sorghum, potato, sesame, ricinus) were placed in plastic pots filled with soil, then covered with 0.5-2 cm of soil, allowed to grow in a good greenhouse environment. After 2 weeks of sowing, the test plants were treated in the 2-3 leaf stage. The tested compounds of the present invention were respectively dissolved in acetone, then added with Tween 80 and 1.5 liter/ha of emulsifiable concentrate of methyl oleate as synergist, diluted with a certain amount of water to obtain a solution with a certain concentration, and sprayed with a spray tower onto the plants. After the application, the plants were cultured for 3 weeks in the greenhouse, and then the experimental results of the weeding were counted. The doses of the used compounds were 500, 250, 125, 60, 15 g a.i./ha, and the averages were obtained by repeating for three times. Representative data are listed in Table 8.

TABLE-US-00004 TABLE 8 Results on weeding effect in post-emergence Stage Veronica Dose Compound Digitaria Echinochloa Setaria Alopecurus Beckmannia didyma Galium Abutilon Amaranthus (g a.i./ No. sanguinalis crusgalli viridis japonicus syzigachne Tenore aparine theophrasti retroflexus ha) 1-2 5 5 5 4 4 5 5 5 5 15 1-10 4 5 5 3 3 5 5 5 5 15 1-12 5 5 5 3 3 5 5 5 5 15 1-33 5 5 5 3 3 5 5 5 5 15 1-35 3 4 5 N N 5 5 5 5 15 1-48 4 5 5 N N 5 5 5 5 15 1-55 5 5 5 N N 5 5 5 5 15 1-62 3 5 5 N N 5 5 5 5 15 1-103 5 5 5 4 4 5 5 5 5 15 1-107 5 5 5 5 5 5 5 5 5 15 1-113 4 5 5 4 4 5 5 5 5 15 1-123 5 5 5 5 5 5 5 5 5 15 2-2 4 N N N N 5 5 5 5 15 2-113 N N N N N 5 5 N 5 15 4-1 N 4 N N N 5 N N 5 15 4-158 N N N N N 5 5 N 5 15 Control 2 3 3 2 2 3 4 4 3 15 compound A Note: N represents no data; Control compound A: [00671]

[0156] Experiment on weed effect in pre-emergence stage:

[0157] The seeds of monocotyledonous and dicotyledonous weeds and main crops (wheat, corn, rice, soybean, cotton, oilseed rape, millet and sorghum) were put into a plastic pot loaded with soil and covered with 0.5-2 cm soil. The test compounds of the present invention was dissolved with acetone, then added with tween 80, diluted by a certain amount of water to reach a certain concentration, and sprayed immediately after sowing. The obtained seeds were incubated for 4 weeks in the greenhouse after spraying and the test results were observed. It was observed that the herbicide mostly had excellent effect at the application rate of 250 g a.i./ha, especially to weeds such as Echinochloa crusgalli, Digitaria sanguinalis and Abutilon theophrasti, etc. And many compounds had good selectivity for corn, wheat, rice, and soybean.

[0158] It is indicated from the experiment of main weeds in wheat and rice fields that the compound of the present invention generally have good weed control efficacy. Above all, it is noted that the compound of the invention have extremely high activity to broad-leaved weeds and cyperaceae weeds, which are resistant to ALS inhibitor, like Sagittaria trifolia, Scirpus juncoides, Cyperus difformis, Descurainia sophia, Capsella bursa-pastoris, Lithospermum arvense, Galium aparine, and Cyperus rotundus L., etc., and have excellent commercial value.

[0159] Transplanted rice safety evaluation and weed control effect evaluation in rice field:

[0160] Rice field soil was loaded into a 1/1,000,000 ha pot. The seeds of Echinochloa crusgalli, Scirpus juncoides, and Bidens tripartita L. were sowed and gently covered with soil, then left to stand still in greenhouse in the state of 0.5-1 cm of water storage. The tuber of Sagittaria trifolia was planted in the next day or 2 days later. It was kept at 3-4 cm of water storage thereafter. The weeds were treated by dripping the WP or SC water diluents prepared according to the common preparation method of the compounds of the present invention with pipette homogeneously to achieve specified effective amount when Echinochloa crusgalli, Scirpus juncoides, and Bidens tripartita L. reached 0.5 leaf stage and Sagittaria trifolia reached the time point of primary leaf stage.

[0161] In addition, the rice field soil that loaded into the 1/1,000,000 ha pot was leveled to keep water storage at 3-4 cm depth. The 3 leaf stage rice (japonica rice) was transplanted at 3 cm of transplanting depth the next day. The compound of the present invention was treated by the same way after 5 days of transplantation.

[0162] The fertility condition of Echinochloa crusgalli, Scirpus juncoides, Bidens tripartita L. and Sagittaria trifolia 14 days after the treatment of the compound of the invention and the fertility condition of rice 21 days after the treatment of the compound of the invention respectively with the naked eye. Evaluate the weed control effect with the above activity standard level. Many compounds show excellent activity and selectivity.

[0163] Note: The seeds of Echinochloa crusgalli, Scirpus juncoides and Bidens tripartita L. were collected from Heilongjiang Province of China. The tests indicated that the weeds were resistant to the common doses of Pyrazosulfuron-ethyl.

[0164] At the same time, it is found after several tests that the compounds and compositions of the present invention have good selectivity to many gramineae grasses such as Zoysia japonica, bermuda grass, tall fescue, bluegrass, ryegrass and seashore paspalum etc, and are able to control many important grass weeds and broad-leaved weeds. The compounds also show excellent selectivity and commercial value in the tests on sugarcane, soybean, cotton, oil sunflower, potato, orchards and vegetables in different herbicide application methods.