ISOXAZOLINE OXIME FORMATE COMPOUND, PREPARATION METHOD THEREFOR, HERBICIDAL COMPOSITION AND USE THEREOF

Abstract

The present invention belongs to the technical field of pesticides, and specifically relates to an isoxazoline oxime formate compound, a preparation method therefor, and a herbicidal composition and a use thereof. The isoxazoline oxime formate compound is shown in general formula I.

##STR00001## Wherein, Y represents halogen, haloalkyl, cyano, nitro or amino; Z represents hydrogen, halogen or hydroxyl; Q represents

##STR00002##

M represents CH or N; X.sub.1, X.sub.2 and X.sub.3 each independently represent hydrogen, etc.; X.sub.4 and X.sub.5 each independently represent hydrogen, halogen, cyano or nitro, etc. The compound also has an excellent herbicidal activity against grassy weeds, broadleaf weeds, etc. at a low application rate, and has a high selectivity to crops.

Claims

1. An isoxazoline oxime formate compound, as shown in general formula I. ##STR00472## wherein, Y represents halogen, halogenated alkyl, cyano, nitro or amino; Z represents hydrogen, halogen or hydroxyl; Q represents ##STR00473## M represents CH or N; X.sub.1, X.sub.2, X.sub.3 each independently represent hydrogen, halogen, nitro, cyano, thiocyano, hydroxyl, sulfhydryl, carboxyl, sulfonic, formyl, halogenated formyl, azido, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, —PO(OR′).sub.2, —(CO)O-alkyl-O—N═C(R′).sub.2, —OR″, —(CO)R″, —SR″, —(SO)R″, —(SO.sub.2)R″, —Si(R″).sub.3, —O(CO)R″, —O—(SO.sub.2)R″, —S(CO)R″, —(SO.sub.2)OR″, —(CO)OR″, —(CO)SR″, —(CS)OR″, —O(CO)OR″, —(CO)(CO)OR″, —(CO)O(CO)R″, —(CO)O(CO)OR″, heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, amino, aminoalkyl, aminocarbonyl, aminocarbonylalkyl, aminocarbonyloxyalkyl, aminothiocarbonyloxyalkyl, aminosulfonyl, or aminosulfonyloxyalkyl, or X.sub.1 and X.sub.2 together form —CH.sub.2CH.sub.2CH.sub.2—, —CH.sub.2CH.sub.2CH.sub.2CH.sub.2—, —CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2—, —OCH.sub.2CH.sub.2—, —OCH.sub.2O—, —OCH.sub.2CH.sub.2O—, —CH.sub.2CH.sub.2OCO— or —CH═CH—CH═CH—; wherein, the “alkyl”, “alkenyl” or “alkynyl” is each independently unsubstituted or substituted with at least one substituent selected from halogen, cyano, hydroxyl, sulfhydryl, carboxyl, —OR″, —(CO)R″, —SR″, —(SO.sub.2)R″, —O(CO)R″, —O—(SO.sub.2)R″, —(CO)OR″ or —O(CO)OR″; the “amino”, “aminoalkyl”, “aminocarbonyl”, “aminocarbonylalkyl”, “aminocarbonyloxyalkyl”, “aminothiocarbonyloxyalkyl”, “aminosulfonyl” or “aminosulfonyloxyalkyl” 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, halogenated alkyl, benzyl, —OR.sub.14, —SR.sub.14, —(CO)OR.sub.14, —(SO.sub.2)R.sub.14, —N(R.sub.14).sub.2 or —O-alkyl-(CO)OR.sub.14; the “—CH.sub.2CH.sub.2CH.sub.2—”, “—CH.sub.2CH.sub.2CH.sub.2CH.sub.2—”, “—CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2—”, “—CH.sub.2OCH.sub.2—”, “—CH.sub.2CH.sub.2OCH.sub.2CH.sub.2—”, “—OCH.sub.2CH.sub.2—”, “—OCH.sub.2O—”, “—OCH.sub.2CH.sub.2O—”, “—CH.sub.2CH.sub.2CO—”, “—CH.sub.2OCO—”, “—CH.sub.2OSO.sub.2—”, “—CH.sub.2CH.sub.2OCO—”, “—CH═CHCOO—”, “—CH═CH—CH═CH—” or “—CH.sub.2CH.sub.2OCO—” is each independently unsubstituted or substituted with halogen; X.sub.4, X.sub.5 each independently represent hydrogen, halogen, cyano, nitro, -(alkyl).sub.n-OR.sub.15, -(alkyl).sub.n-SR.sub.15, -(alkyl).sub.n-(CO)R.sub.15, -(alkyl).sub.n-O(CO)R.sub.11, -(alkyl).sub.n-(CO)OR.sub.11, -(alkyl).sub.n-(CO)SR.sub.15, aminocarbonyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, or the CX.sub.4X.sub.5 group together forms ring structure; wherein, the “aminocarbonyl” is 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 “alkyl”, “alkenyl” or “alkynyl” is each independently unsubstituted or substituted with 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, halogenated alkyl, benzyl, —OR.sub.14, —SR.sub.14, —(CO)OR.sub.14, —(SO.sub.2)R.sub.14, —N(R.sub.14).sub.2 or —O-alkyl-(CO)OR.sub.14, or two adjacent carbon atoms on the ring together with —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; Q.sub.1, Q.sub.2, Q.sub.3, Q.sub.4, Q.sub.5 each independently represent oxygen or sulphur; 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—, ##STR00474## 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 with 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, halogenated alkyl, benzyl, —OR.sub.14, —SR.sub.14, —(CO)OR.sub.14, —(SO.sub.2)R.sub.14, —N(R.sub.14).sub.2 or —O-alkyl-(CO)OR.sub.14; R.sub.6, R.sub.7 each independently represent hydrogen, alkyl or halogenated alkyl; R′ each independently represents hydrogen, halogen, alkoxy, alkoxyalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, or the C(R′).sub.2 group in —(CO)O-alkyl-O—N═C(R′).sub.2 together forms ring structure; wherein, the “alkyl”, “alkenyl” or “alkynyl” is each independently unsubstituted or substituted with 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, halogenated alkyl, benzyl, —OR.sub.14, —SR.sub.14, —(CO)OR.sub.14, —(SO.sub.2)R.sub.14, —N(R.sub.14).sub.2 or —O-alkyl-(CO)OR.sub.14; R″ each independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, arylalkenyl, heterocyclyl, heterocyclylalkyl or heterocyclylalkenyl; wherein, the “alkyl”, “alkenyl” or “alkynyl” is each independently unsubstituted or substituted with at least one substituent selected from halogen, cyano, trialkylsilyl, —OR.sub.13, —SR.sub.13, —O(CO)R.sub.13, —(CO)R.sub.13, —(CO)OR.sub.13 or —O(CO)OR.sub.13; the “cycloalkyl”, “cycloalkylalkyl”, “cycloalkenyl”, “cycloalkenylalkyl”, “aryl”, “arylalkyl”, “arylalkenyl”, “heterocyclyl”, “heterocyclylalkyl” or “heterocyclylalkenyl” is each independently unsubstituted or substituted with at least one substituent selected from oxo, halogen, cyano, nitro, alkyl, halogenated alkyl, benzyl, —OR.sub.14, —SR.sub.14, —(CO)OR.sub.14, —(SO.sub.2)R.sub.14, —N(R.sub.14).sub.2 or —O-alkyl-(CO)OR.sub.14; R.sub.3, R.sub.4, R.sub.5, R.sub.15 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 with 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, halogenated alkyl, benzyl, —OR.sub.14, —SR.sub.14, —(CO)OR.sub.14, —(SO.sub.2)R.sub.14, —N(R.sub.14).sub.2 or —O-alkyl-(CO)OR.sub.14; 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 with 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 N(R.sub.12).sub.2 group in —(CO)N(R.sub.12).sub.2 or —(SO.sub.2)N(R.sub.12).sub.2 each independently represents heterocyclyl with nitrogen atom at 1-position; R.sub.13 each independently represents alkyl, alkenyl, alkynyl, cycloalkyl, phenyl or phenyl substituted with at least one substituent selected from halogen, cyano, nitro, alkyl, halogenated alkyl, alkoxy, halogenated alkoxy, alkoxycarbonyl, alkylthio, alkylsulfonyl or phenoxyl substituted with at least one substituent selected from halogen, cyano, nitro, alkyl, halogenated alkyl, alkoxy or halogenated alkoxy; R.sub.14 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 isoxazoline oxime formate compound according to claim 1, which is characterized in that, Y represents halogen, halogenated C1-C8 alkyl, cyano, nitro or amino; X.sub.1, X.sub.2, X.sub.3 each independently represent hydrogen, halogen, nitro, cyano, thiocyano, hydroxyl, sulfhydryl, carboxyl, sulfonic, formyl, halogenated formyl, azido, 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, —PO(OR′).sub.2, —(CO)O—(C1-C8 alkyl)-O—N═C(R′).sub.2, —OR″, —(CO)R″, —SR″, —(SO)R″, —(SO.sub.2)R″, —Si(R″).sub.3, —O(CO)R″, —O—(SO.sub.2)R″, —S(CO)R″, —(SO.sub.2)OR″, —(CO)OR″, —(CO)SR″, —(CS)OR″, —O(CO)OR″, —(CO)(CO)OR″, —(CO)O(CO)R″, —(CO)O(CO)OR″, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, amino, amino C1-C8 alkyl, aminocarbonyl, aminocarbonyl C1-C8 alkyl, aminocarbonyloxy C1-C8 alkyl, aminothiocarbonyloxy C1-C8 alkyl, aminosulfonyl, or aminosulfonyloxy C1-C8 alkyl, or X.sub.1 and X.sub.2 together form —CH.sub.2CH.sub.2CH.sub.2—, —CH.sub.2CH.sub.2CH.sub.2CH.sub.2—, —CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2—, —OCH.sub.2CH.sub.2—, —OCH.sub.2O—, —OCH.sub.2CH.sub.2O—, —CH.sub.2CH.sub.2OCO— or —CH═CH—CH═CH—; wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl” or “C2-C8 alkynyl” is each independently unsubstituted or substituted with one to four substituents selected from halogen, cyano, hydroxyl, sulfhydryl, carboxyl, —OR″, —(CO)R″, —SR″, —(SO.sub.2)R″, —O(CO)R″, —O—(SO.sub.2)R″, —(CO)OR″ or —O(CO)OR″; the “amino”, “amino C1-C8 alkyl”, “aminocarbonyl”, “aminocarbonyl C1-C8 alkyl”, “aminocarbonyloxy C1-C8 alkyl”, “aminothiocarbonyloxy C1-C8 alkyl”, “aminosulfonyl” or “aminosulfonyloxy C1-C8 alkyl” 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 one to four substituents selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, benzyl, —OR.sub.14, —SR.sub.14, —(CO)OR.sub.14, —(SO.sub.2)R.sub.14, —N(R.sub.14).sub.2 or —O—(C1-C8 alkyl)-(CO)OR.sub.14; the “—CH.sub.2CH.sub.2CH.sub.2—”, “—CH.sub.2CH.sub.2CH.sub.2CH.sub.2—”, “—CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2—”, “—CH.sub.2OCH.sub.2—”, “—CH.sub.2CH.sub.2OCH.sub.2CH.sub.2—”, “—OCH.sub.2CH.sub.2—”, “—OCH.sub.2O—”, “—OCH.sub.2CH.sub.2O—”, “—CH.sub.2CH.sub.2CO—”, “—CH.sub.2OCO—”, “—CH.sub.2OSO.sub.2—”, “—CH.sub.2CH.sub.2OCO—”, “—CH═CHCOO—”, “—CH═CH—CH═CH—” or “—CH.sub.2CH.sub.2OCO—” is each independently unsubstituted or substituted with halogen; X.sub.4, X.sub.5 each independently represent hydrogen, halogen, cyano, nitro, —(C1-C8 alkyl).sub.n-OR.sub.15, —(C1-C8 alkyl).sub.n-SR.sub.15, —(C1-C8 alkyl).sub.n-(CO)R.sub.15, —(C1-C8 alkyl).sub.n-O(CO)R.sub.15, —(C1-C8 alkyl).sub.n-(CO)OR.sub.15, —(C1-C8 alkyl).sub.n-(CO)SR.sub.15, aminocarbonyl, 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.4X.sub.5 group together forms 5- to 8-membered carbocyclyl or oxygen-, sulfur- or nitrogen-containing heterocyclyl; wherein, the “aminocarbonyl” is 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)Ru, —(CO)N(R.sub.12).sub.2 or —(SO.sub.2)N(R.sub.12).sub.2; the “C1-C8 alkyl”, “C2-C8 alkenyl” or “C2-C8 alkynyl” is each independently unsubstituted or substituted with 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 one to four substituents selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, benzyl, —OR.sub.14, —SR.sub.14, —(CO)OR.sub.14, —(SO.sub.2)R.sub.14, —N(R.sub.14).sub.2 or —O—(C.sub.1-C.sub.8 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring together with —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 one to four substituents selected from C1-C8 alkyl, C1-C8 alkoxycarbonyl or benzyl, or forms a fused ring structure with aryl or heterocyclyl; 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—, ##STR00475## 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 with 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 one to four substituents selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, benzyl, —OR.sub.14, —SR.sub.14, —(CO)OR.sub.14, —(SO.sub.2)R.sub.14, —N(R.sub.14).sub.2 or —O—(C1-C8 alkyl)-(CO)OR.sub.14; R.sub.6, R.sub.7 each independently represent hydrogen, C1-C8 alkyl or halogenated C1-C8 alkyl; R′ each 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, heterocyclyl or heterocyclyl C1-C8 alkyl, or the C(R′).sub.2 group in —(CO)O—(C1-C8 alkyl)-O—N═C(R′).sub.2 together forms a 5- to 6-membered saturated carbocyclyl; wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl” or “C2-C8 alkynyl” is each independently unsubstituted or substituted with 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 one to four substituents selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, benzyl, —OR.sub.14, —SR.sub.14, —(CO)OR.sub.14, —(SO.sub.2)R.sub.14, —N(R.sub.14).sub.2 or —O—(C1-C8 alkyl)-(CO)OR.sub.14; R″ 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, aryl, aryl C1-C8 alkyl, aryl C2-C8 alkenyl, heterocyclyl, heterocyclyl C1-C8 alkyl or heterocyclyl C2-C8 alkenyl; wherein, the “C1-C8 alkyl”, “C2-C8 alkenyl” or “C2-C8 alkynyl” is each independently unsubstituted or substituted with one to three substituents selected from halogen, cyano, tri-C1-C8 alkylsilyl, —OR.sub.13, —SR.sub.13, —O(CO)R.sub.13, —(CO)R.sub.13, —(CO)OR.sub.13 or —O(CO)OR.sub.13; the “C3-C8 cycloalkyl”, “C3-C8 cycloalkyl C1-C8 alkyl”, “C3-C8 cycloalkenyl”, “C3-C8 cycloalkenyl C1-C8 alkyl”, “aryl”, “aryl C1-C8 alkyl”, “aryl C2-C8 alkenyl”, “heterocyclyl”, “heterocyclyl C1-C8 alkyl” or “heterocyclyl C2-C8 alkenyl” is each independently unsubstituted or substituted with one to four substituents selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, benzyl, —OR.sub.14, —SR.sub.14, —(CO)OR.sub.14, —(SO.sub.2)R.sub.14, —N(R.sub.14).sub.2 or —O—(C1-C8 alkyl)-(CO)OR.sub.14; R.sub.3, R.sub.4, R.sub.5, R.sub.15 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 with 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 one to four substituents selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, benzyl, —OR.sub.14, —SR.sub.14, —(CO)OR.sub.14, —(SO.sub.2)R.sub.14, —N(R.sub.14).sub.2 or —O—(C1-C8 alkyl)-(CO)OR.sub.14; Rn 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 with halogen; the “phenyl” or “benzyl” is each independently unsubstituted or substituted with one to four substituents 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 in —(CO)N(R.sub.12).sub.2 or —(SO.sub.2)N(R.sub.12).sub.2 each independently represents heterocyclyl ##STR00476## with nitrogen atom at 1-position; R.sub.13 each independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, phenyl or phenyl substituted with one to four substituents selected from halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxy, halogenated C1-C8 alkoxy, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl or phenoxyl substituted with one to four substituents selected from halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxy or halogenated C1-C8 alkoxy; R.sub.14 each independently represents hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, phenyl or phenyl substituted with one to four substituents 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 isoxazoline oxime formate compound according to claim 1, which is characterized in that, Y represents halogen, halogenated C1-C6 alkyl, cyano, nitro or amino; X.sub.1, X.sub.2, X.sub.3 each independently represent hydrogen, halogen, nitro, cyano, thiocyano, hydroxyl, sulfhydryl, carboxyl, sulfonic, formyl, halogenated formyl, azido, 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, —PO(OR′).sub.2, —(CO)O—(C1-C6 alkyl)-O—N═C(R′).sub.2, —OR″, —(CO)R″, —SR″, —(SO)R″, —(SO.sub.2)R″, —Si(R″).sub.3, —O(CO)R″, —O—(SO.sub.2)R″, —S(CO)R″, —(SO.sub.2)OR″, —(CO)OR″, —(CO)SR″, —(CS)OR″, —O(CO)OR″, —(CO)(CO)OR″, —(CO)O(CO)R″, —(CO)O(CO)OR″, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, amino, amino C1-C6 alkyl, aminocarbonyl, aminocarbonyl C1-C6 alkyl, aminocarbonyloxy C1-C6 alkyl, aminothiocarbonyloxy C1-C6 alkyl, aminosulfonyl, or aminosulfonyloxy C1-C6 alkyl, or X.sub.1 and X.sub.2 together form —CH.sub.2CH.sub.2CH.sub.2—, —CH.sub.2CH.sub.2CH.sub.2CH.sub.2—, —CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2—, —OCH.sub.2CH.sub.2—, —OCH.sub.2O—, —OCH.sub.2CH.sub.2O—, —CH.sub.2CH.sub.2OCO— or —CH═CH—CH═CH—; 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, hydroxyl, sulfhydryl, carboxyl, —OR″, —(CO)R″, —SR″, —(SO.sub.2)R″, —O(CO)R″, —O—(SO.sub.2)R″, —(CO)OR″ or —O(CO)OR″; the “amino”, “amino C1-C6 alkyl”, “aminocarbonyl”, “aminocarbonyl C1-C6 alkyl”, “aminocarbonyloxy C1-C6 alkyl”, “aminothiocarbonyloxy C1-C6 alkyl”, “aminosulfonyl” or “aminosulfonyloxy C1-C6 alkyl” 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)Ru, —(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, halogenated C1-C6 alkyl, benzyl, —OR.sub.14, —SR.sub.14, —(CO)OR.sub.14, —(SO.sub.2)R.sub.14, —N(R.sub.14).sub.2 or —O—(C1-C6 alkyl)-(CO)OR.sub.14; the “—CH.sub.2CH.sub.2CH.sub.2—”, “—CH.sub.2CH.sub.2CH.sub.2CH.sub.2—”, “—CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2—”, “—CH.sub.2OCH.sub.2—”, “—CH.sub.2CH.sub.2OCH.sub.2CH.sub.2—”, “—OCH.sub.2CH.sub.2—”, “—OCH.sub.2O—”, “—OCH.sub.2CH.sub.2O—”, “—CH.sub.2CH.sub.2CO—”, “—CH.sub.2OCO—”, “—CH.sub.2OSO.sub.2—”, “—CH.sub.2CH.sub.2OCO—”, “—CH═CHCOO—”, “—CH═CH—CH═CH—” or “—CH.sub.2CH.sub.2OCO—” is each independently unsubstituted or substituted with halogen; X.sub.4, X.sub.5 each independently represent hydrogen, halogen, cyano, nitro, —(C1-C6 alkyl).sub.n-OR.sub.15, —(C1-C6 alkyl).sub.n-SR.sub.15, —(C1-C6 alkyl).sub.n-(CO)R.sub.15, —(C1-C6 alkyl).sub.n-O(CO)R.sub.15, —(C1-C6 alkyl).sub.n-(CO)OR.sub.15, —(C1-C6 alkyl).sub.n-(CO)SR.sub.15, aminocarbonyl, 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.4X.sub.5 group together forms 5- to 8-membered carbocyclyl or oxygen-, sulfur- or nitrogen-containing heterocyclyl; wherein, the “aminocarbonyl” is 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 “C1-C6 alkyl”, “C2-C6 alkenyl” or “C2-C6 alkynyl” is each independently unsubstituted or substituted with 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, halogenated C1-C6 alkyl, benzyl, —OR.sub.14, —SR.sub.14, —(CO)OR.sub.14, —(SO.sub.2)R.sub.14, —N(R.sub.14).sub.2 or —O—(C1-C6 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring together with —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 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; 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—, ##STR00477## 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 with 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, halogenated C1-C6 alkyl, benzyl, —OR.sub.14, —SR.sub.14, —(CO)OR.sub.14, —(SO.sub.2)R.sub.14, —N(R.sub.14).sub.2 or —O—(C1-C6 alkyl)-(CO)OR.sub.14; R.sub.6, R.sub.7 each independently represent hydrogen, C1-C6 alkyl or halogenated C1-C6 alkyl; R′ each independently represents hydrogen, halogen, C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, 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 C(R′).sub.2 group in —(CO)O—(C1-C6 alkyl)-O—N═C(R′).sub.2 together forms a 5- to 6-membered saturated carbocyclyl; wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” or “C2-C6 alkynyl” is each independently unsubstituted or substituted with 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, halogenated C1-C6 alkyl, benzyl, —OR.sub.14, —SR.sub.14, —(CO)OR.sub.14, —(SO.sub.2)R.sub.14, —N(R.sub.14).sub.2 or —O—(C1-C6 alkyl)-(CO)OR.sub.14; R″ 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, aryl, aryl C1-C6 alkyl, aryl C2-C6 alkenyl, heterocyclyl, heterocyclyl C1-C6 alkyl or heterocyclyl C2-C6 alkenyl; 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, tri-C1-C8 alkylsilyl, —OR.sub.13, —SR.sub.13, —O(CO)R.sub.13, —(CO)R.sub.13, —(CO)OR.sub.13 or —O(CO)OR.sub.13; the “C3-C6 cycloalkyl”, “C3-C6 cycloalkyl C1-C6 alkyl”, “C3-C6 cycloalkenyl”, “C3-C6 cycloalkenyl C1-C6 alkyl”, “aryl”, “aryl C1-C6 alkyl”, “aryl C2-C6 alkenyl”, “heterocyclyl”, “heterocyclyl C1-C6 alkyl” or “heterocyclyl C2-C6 alkenyl” is each independently unsubstituted or substituted with one, two or three substituents selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, benzyl, —OR.sub.14, —SR.sub.14, —(CO)OR.sub.14, —(SO.sub.2)R.sub.14, —N(R.sub.14).sub.2 or —O—(C1-C6 alkyl)-(CO)OR.sub.14; R.sub.3, R.sub.4, R.sub.5, R.sub.15 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 with 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, halogenated C1-C6 alkyl, benzyl, —OR.sub.14, —SR.sub.14, —(CO)OR.sub.14, —(SO.sub.2)R.sub.14, —N(R.sub.14).sub.2 or —O—(C1-C6 alkyl)-(CO)OR.sub.14; 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 with 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 in —(CO)N(R.sub.12).sub.2 or —(SO.sub.2)N(R.sub.12).sub.2 each independently represents heterocyclyl ##STR00478## with nitrogen atom at 1-position; R.sub.13 each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, phenyl or phenyl substituted with one, two or three substituents selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl or phenoxyl substituted with one, two or three substituents selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy; R.sub.14 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 isoxazoline oxime formate compound according to claim 1, which is characterized in that, X.sub.4, X.sub.5 each independently represent hydrogen, halogen, cyano, nitro, —(C1-C3 alkyl).sub.n-OR.sub.15, —(C1-C3 alkyl).sub.n-SR.sub.15, —(C1-C3 alkyl).sub.n-(CO)R.sub.15, —(C1-C3 alkyl).sub.n-O(CO)R.sub.15, —(C1-C3 alkyl).sub.n-(CO)OR.sub.15, —(C1-C3 alkyl).sub.n-(CO)SR.sub.15, aminocarbonyl, 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.4X.sub.5 group together forms a 5- to 8-membered saturated carbocyclyl, ##STR00479## wherein, the “aminocarbonyl” is 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-C3 alkyl)-(CO)OR.sub.11, —(SO.sub.2)R.sub.11, —(SO.sub.2)OR.sub.11, —(C1-C3 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 “C1-C6 alkyl”, “C2-C6 alkenyl” or “C2-C6 alkynyl” is each independently unsubstituted or substituted with 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, halogenated C1-C6 alkyl, benzyl, —OR.sub.14, —SR.sub.14, —(CO)OR.sub.14, —(SO.sub.2)R.sub.14, —N(R.sub.14).sub.2 or —O—(C1-C3 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring together with —OCH.sub.2CH.sub.2— or —OCH.sub.2O— form a fused ring; the “5- to 8-membered saturated carbocyclyl, ##STR00480## 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 thienyl; R.sub.15 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 “C1-C6 alkyl”, “C2-C6 alkenyl” or “C2-C6 alkynyl” is each independently unsubstituted or substituted with halogen; 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, halogenated C1-C6 alkyl, benzyl, —OR.sub.14, —SR.sub.14, —(CO)OR.sub.14, —(SO.sub.2)R.sub.14, —N(R.sub.14).sub.2 or —O—(C1-C3 alkyl)-(CO)OR.sub.14; R.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, phenyl or benzyl; wherein, the “C1-C6 alkyl”, “C2-C6 alkenyl” or “C2-C6 alkynyl” is each independently unsubstituted or substituted with 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-C3 alkyl, C3-C6 cycloalkenyl or C3-C6 cycloalkenyl C1-C3 alkyl; or the N(R.sub.12).sub.2 group in —(CO)N(R.sub.12).sub.2 or —(SO.sub.2)N(R.sub.12).sub.2 each independently represents heterocyclyl ##STR00481## or with nitrogen atom at 1-position; R.sub.14 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 isoxazoline oxime formate compound according to claim 1, which is characterized in that, Y represents chlorine; Z represents fluorine; X.sub.1, X.sub.2, X.sub.3 each independently represent hydrogen or C1-C6 alkyl; X.sub.4, X.sub.5 each independently represent hydrogen, —(C1-C3 alkyl).sub.n-OR.sub.15, —(CO)OR.sub.15, C1-C6 alkyl, C3-C6 cycloalkyl, phenyl or heterocyclyl, or the CX.sub.4X.sub.5 group together forms a 5- to 6-membered saturated carbocyclyl; wherein, the “C3-C6 cycloalkyl”, “phenyl” or “heterocyclyl” is each independently unsubstituted or substituted with one, two or three substituents selected from C1-C6 alkyl; the “heterocyclyl” is selected from ##STR00482## Q.sub.1, Q.sub.2, Q.sub.3 each independently represent oxygen or sulphur; 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; R.sub.15 each independently represents C1-C6 alkyl;

6. A method for preparing the isoxazoline oxime formate 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 condensation reaction to obtain a compound as shown in general formula I, with the chemical reaction equation shown as follows: ##STR00483## wherein, the substituents Q, Y, Z, X.sub.1, X.sub.2, X.sub.3, X.sub.4 and X.sub.5 are defined according to claim 1.

7. The method for preparing the isoxazoline oxime formate compound according to claim 6, which is characterized in that, the reaction is carried out under the action of base and condensing agent in the present of aprotic solvent; the condensing agent is PyBop, HATU or HOBt-EDCI; the solvent is one or more mixed solvents selected from dichloromethane, dichlorethane, acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, tetrahydrofuran, toluene and xylene.

8. An herbicidal composition, which characterized by comprising at least one of the isoxazoline oxime formate compound according to claim 1 in a herbicidally effective amount.

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

10. (canceled)

11. The isoxazoline oxime formate compound according to claim 1, wherein the isoxazoline oxime formate compound is selected from any one in Table 1.

12. The isoxazoline oxime formate compound according to claim 5, wherein Q represents ##STR00484##

13. The method for preparing the isoxazoline oxime formate compound according to claim 7, wherein the base is one or more selected from triethylamine, trimethylamine, DIPEA and DBU.

14. The herbicidal composition according to claim 8, which further comprises a formulation auxiliary.

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

Description

SPECIFIC MODE FOR CARRYING OUT THE INVENTION

[0130] 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.

[0131] 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 I [00023] NO. Q [00024] Y Z M .sup.1H NMR 1 [00025] [00026] Cl F CH 2 [00027] [00028] Cl F CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.03-7.90 (m, 3H), 3.98 (d, J = 17.5 Hz, 1H), 3.64 (s, 6H), 3.57 (d, J = 17.5 Hz, 1H), 1.98 (d, J = 6.0 Hz, 3H), 1.70 (s, 3H). 3 [00029] [00030] Cl F CH 4 [00031] [00032] Cl F CH 5 [00033] [00034] Cl F CH 6 [00035] [00036] CF.sub.3 F CH 7 [00037] [00038] Br F CH 8 [00039] [00040] Cl H CH 9 [00041] [00042] Cl Cl CH 10 [00043] [00044] Cl F CH .sup.1H NMR (500 MHz, DMSO-d6) δ 7.95 (d, J = 7.5 Hz, 1H), 7.90 (d, J = 9.5 Hz, 1H), 3.96 (d, J = 17.5 Hz, 1H), 3.63 (s, 6H), 3.59 (d, J = 17.5 Hz, 1H), 1.98 (s, 3H), 1.96 (s, 3H), 1.62 (s, 3H) 11 [00045] [00046] Cl OH CH 12 [00047] [00048] CN H CH 13 [00049] [00050] CN F CH 14 [00051] [00052] NO.sub.2 F CH 15 [00053] [00054] NH.sub.2 F CH 16 [00055] [00056] Cl F N .sup.1H NMR (500 MHz, Chloroform-d) δ 7.61 (d, J = 8.0 Hz, 1H), 3.81 (s, 6H), 3.41 (d, J = 18.0 Hz, 1H), 2.87 (d, J = 18.0 Hz, 1H), 2.64 (s, 6H), 1.54 (s, 3H). 17 [00057] [00058] Cl H N 18 [00059] [00060] CN H N 19 [00061] [00062] Cl F CH 20 [00063] [00064] Cl F CH 21 [00065] [00066] Cl F CH 22 [00067] [00068] Cl F CH 23 [00069] [00070] Cl F CH 24 [00071] [00072] Cl F CH 25 [00073] [00074] Cl F CH 26 [00075] [00076] Cl F CH 27 [00077] [00078] Cl F CH 28 [00079] [00080] Cl F CH 29 [00081] [00082] Cl F CH 30 [00083] [00084] Cl F CH 31 [00085] [00086] Cl F CH 32 [00087] [00088] Cl F CH 33 [00089] [00090] Cl F CH 34 [00091] [00092] Cl F CH 35 [00093] [00094] Cl F CH 36 [00095] [00096] Cl F CH 37 [00097] [00098] Cl F CH 38 [00099] [00100] Cl F CH 39 [00101] [00102] Cl F CH 40 [00103] [00104] Cl F CH 41 [00105] [00106] Cl F CH 42 [00107] [00108] Cl F CH 43 [00109] [00110] Cl F CH 44 [00111] [00112] Cl F CH 45 [00113] [00114] Cl F CH 46 [00115] [00116] Cl F CH 47 [00117] [00118] Cl F CH 48 [00119] [00120] Cl F CH 49 [00121] [00122] Cl F CH 50 [00123] [00124] Cl F CH 51 [00125] [00126] Cl F CH 52 [00127] [00128] Cl F CH 53 [00129] [00130] Cl F CH 54 [00131] [00132] Cl F CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.01-7.98 (m, 1H), 7.97 (d, J = 7.5 Hz, 1H), 7.90 (d, J = 9.5 Hz, 1H), 4.15 (s, 3H), 4.00-3.94 (m, 1H), 3.63 (s, 3H), 3.62-3.57 (m, 1H), 1.97 (d, J = 6.0 Hz, 3H), 1.70 (s, 3H). 55 [00133] [00134] Cl F CH 56 [00135] [00136] Cl F CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.95 (d, J = 7.5 Hz, 1H), 7.90 (d, J = 9.5 Hz, 1H), 4.15 (s, 3H), 4.01- 3.94 (m, 1H), 3.68 (s, 3H), 3.62- 3.55 (m, 1H), 1.98 (s, 3H), 1.96 (s, 3H), 1.62 (d, J = 5.5 Hz, 3H) 57 [00137] [00138] Cl F CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.98 (d, J = 7.5 Hz, 1H), 7.90 (d, J = 9.5 Hz, 1H), 4.15 (s, 3H), 4.01- 3.93 (m, 1H), 3.63 (s, 3H), 3.62- 3.57 (m, 1H), 2.39-2.32 (m, 2H), 1.96 (s, 3H), 1.72 (s, 3H), 1.11- 1.00 (m, 3H). 58 [00139] [00140] Cl F CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.97 (d, J = 7.5 Hz, 1H), 7.90 (d, J = 9.5 Hz, 1H), 4.15 (s, 3H), 3.97 (dd, J = 17.5 Hz, 1H), 3.64 (s, 3H), 3.60 (dd, J = 17.5 Hz, 1H), 2.64 (p, J = 7.0 Hz, 1H), 1.92 (s, 3H), 1.71 (s, 3H), 1.11 (d, J = 7.0 Hz, 6H). 59 [00141] [00142] Cl F CH .sup.1H NMR (500 MHz, DMSO-d6) δ 7.97 (d, J = 7.5 Hz, 1H), 7.90 (d, J = 9.5 Hz, 1H), 3.98 (dd, J = 17.5 Hz, 1H), 4.15 (s, 3H), 3.63 (s, 3H), 3.62-3.57 (m, 1H), 1.95 (s, 3H), 1.72 (s, 3H), 1.16 (s, 9H). 60 [00143] [00144] Cl F CH .sup.1H NMR (500 MHz, DMSO) δ 7.98 (d, J = 7.5 Hz, 1H), 7.90 (d, J = 9.5 Hz, 1H), 4.15 (s, 3H), 4.01- 3.92 (m, 1H), 3.63 (s, 3H), 3.62-3.57 (m, 1H), 2.40- 2.32 (m, 4H), 1.71 (s, 3H), 1.09 (t, J = 7.5 Hz, 3H), 1.02 (t, J = 7.5 Hz, 3H). 61 [00145] [00146] Cl F CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.96 (d, J = 7.5 Hz, 1H), 7.90 (d, J = 9.5 Hz, 1H), 4.15 (s, 3H), 3.96 (dd, J = 17.5 Hz, 1H), 3.63 (s, 3H), 3.60 (dd, J = 17.5 Hz, 1H), 1.73 (s, 3H), 1.71 (s, 3H), 0.97-0.78 (m, 5H). 62 [00147] [00148] Cl F CH 63 [00149] [00150] Cl F CH 64 [00151] [00152] Cl F CH 65 [00153] [00154] Cl F CH 66 [00155] [00156] Cl F CH 67 [00157] [00158] Cl F CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.97 (d, J = 7.5 Hz, 1H), 7.90 (d, J = 9.5 Hz, 1H), 4.15 (s, 3H), 4.14- 4.09 (m, 2H), 3.98 (dd, J = 17.5 Hz, 1H), 3.63 (s, 3H), 3.60 (dd, J = 17.5 Hz, 1H), 2.02 (s, 3H), 1.72 (s, 3H), 1.29 (t, J = 7.0 Hz, 3H). 68 [00159] [00160] Cl F CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.97 (d, J = 7.5 Hz, 1H), 7.90 (d, J = 9.5 Hz, 1H), 4.15 (s, 3H), 4.08 (s, 2H), 3.99 (dd, J = 17.5 Hz, 1H), 3.65-3.60 (m, 4H), 3.29 (s, 3H), 1.98 (s, 3H), 1.73 (s, 3H). 69 [00161] [00162] Cl F CH .sup.1H NMR (500 MHz, DMSO) δ 8.82 (s, 1H), 8.00 (d, J = 7.5 Hz, 1H), 7.91 (d, J = 9.5 Hz, 1H), 7.80-7.78 (m, 2H), 7.61-7.56 (m, 1H), 7.56-7.52 (m, 2H), 4.15 (s, 3H), 4.06-4.01 (m, 1H), 3.70- 3.62 (m, 1H), 3.63 (s, 3H), 1.77 (s, 3H). 70 [00163] [00164] Cl F CH .sup.1H NMR (500 MHz, DMSO) δ 7.98 (d, J = 7.5 Hz, 1H), 7.90 (d, J = 9.0 Hz, 1H), 7.82- 7.75 (m, 2H), 7.55- 7.46 (m, 3H), 4.14 (s, 3H), 4.09- 4.01 (m, 1H), 3.70- 3.65 (m, 1H), 3.62 (s, 3H), 2.39 (s, 3H), 1.77 (s, 3H). 71 [00165] [00166] Cl F CH .sup.1H NMR (500 MHz, DMSO) δ 7.90 (d, J = 7.5 Hz, 1H), 7.86 (d, J = 9.0 Hz, 1H), 7.58-7.52 (m, 1H), 7.54-7.45 (m, 4H), 7.43- 7.40 (m, 3H), 7.33- 7.30 (m, 2H), 4.14 (s, 3H), 3.69- 3.62 (m, 1H), 3.62 (s, 3H), 3.48- 3.42 (m, 1H), 1.51 (s, 3H). 72 [00167] [00168] Cl F CH 73 [00169] [00170] Cl F CH 74 [00171] [00172] Cl F CH .sup.1H NMR (500 MHz, DMSO) δ 7.96 (d, J = 7.5 Hz, 1H), 7.88 (d, J = 9.5 Hz, 1H), 4.13 (s, 3H), 3.96- 3.90 (m, 1H), 3.62 (s, 3H), 3.61- 3.55 (m, 1H), 2.49-2.44 (m, 4H), 2.26-2.22 (m, 4H), 1.69 (s, 3H). 75 [00173] [00174] Cl F CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.98 (d, J = 7.5 Hz, 1H), 7.91 (d, J = 9.5 Hz, 1H), 4.31 (q, J = 7.0 Hz, 2H), 4.15 (s, 3H), 4.04 (dd, J = 17.5, 9.0 Hz, 1H), 3.71-3.62 (m, 4H), 2.16 (s, 3H), 1.76 (s, 3H), 1.29 (t, J = 7.0 Hz, 3H). 76 [00175] [00176] Cl F CH 77 [00177] [00178] Cl F CH 78 [00179] [00180] Cl F CH 79 [00181] [00182] Cl F CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.98-7.92 (m, 2H), 3.98 (d, J = 17.5, 1H), 3.64-3.62 (m, 7H), 2.43-2.28 (m, 2H), 1.96 (s, 3H), 1.71 (s, 3H), 1.09 (t, J = 7.5 Hz, 3H). 80 [00183] [00184] Cl F CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.95 (d, J = 7.5 Hz, 1H), 7.91 (d, J = 9.5 Hz, 1H), 3.96 (d, J = 17.5 Hz, 1H), 3.62 (s, 6H), 3.58 (d, J = 17.5 Hz, 1H), 2.64-2.58 (m, 1H), 1.91 (s, 3H), 1.69 (s, 3H), 1.09 (d, J = 7.0 Hz, 6H). 81 [00185] [00186] Cl F CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.91-7.98 (m, 2H), 4.01-3.97 (m, 1H), 3.65 (s, 6H), 3.62-3.58 (m, 1H), 1.96 (s, 3H), 1.72 (s, 3H), 1.16 (s, 9H). 82 [00187] [00188] Cl F CH 83 [00189] [00190] Cl F CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.98 (d, J = 7.5 Hz, 1H), 7.93 (d, J = 9.5 Hz, 1H), 3.98 (d, J = 17.5 Hz, 1H), 3.64-3.63 (m, 7H), 2.39-2.35 (m, 4H), 1.72 (s, 3H), 1.10 (t, J = 7.5 Hz, 3H), 1.03 (t, J = 7.5 Hz, 3H). 84 [00191] [00192] Cl F CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.95 (d, J = 7.5 Hz, 1H), 7.91 (d, J = 9.5 Hz, 1H), 3.97 (d, J = 17.5 Hz, 1H), 3.63 (s, 6H), 3.58 (d, J = 17.5 Hz, 1H), 2.25- 2.19 (m, 1H), 1.71 (s, 3H), 1.65 (s, 3H), 0.97- 0.88 (m, 4H). 85 [00193] [00194] Cl F CH 86 [00195] [00196] Cl F CH 87 [00197] [00198] Cl F CH 88 [00199] [00200] Cl F CH 89 [00201] [00202] Cl F CH 90 [00203] [00204] Cl F CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.83 (s, 1H), 8.01 (d, J = 7.5 Hz, 1H), 7.94 (d, J = 9.5 Hz, 1H), 7.86-7.76 (m, 2H), 7.65-7.45 (m, 3H), 4.06 (d, J = 17.5 Hz, 1H), 3.68-3.65 (m, 7H), 1.77 (s, 3H). 91 [00205] [00206] Cl F CH 92 [00207] [00208] Cl F CH 93 [00209] [00210] Cl F CH 94 [00211] [00212] Cl F CH 95 [00213] [00214] Cl F CH 96 [00215] [00216] Cl F CH 97 [00217] [00218] Cl F CH 98 [00219] [00220] Cl F CH 99 [00221] [00222] Cl F CH 100 [00223] [00224] Cl F CH 101 [00225] [00226] Cl F CH 102 [00227] [00228] Cl F CH 103 [00229] [00230] Cl F CH 104 [00231] [00232] Cl F CH 105 [00233] [00234] Cl F CH 106 [00235] [00236] Cl F CH 107 [00237] [00238] Cl F CH 108 [00239] [00240] Cl F CH 109 [00241] [00242] Cl F CH 110 [00243] [00244] Cl F CH 111 [00245] [00246] Cl F CH 112 [00247] [00248] Cl F CH 113 [00249] [00250] Cl F CH 114 [00251] [00252] Cl F CH 115 [00253] [00254] Cl F CH 116 [00255] [00256] Cl F CH 117 [00257] [00258] Cl F CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.59 (s, 1H), 8.05-7.86 (m, 2H), 7.04 (d, J = 3.5 Hz, 1H), 6.38 (d, J = 3.5 Hz, 1H), 4.04 (d, J = 17.5 Hz, 1H), 3.65 (s, 6H), 3.64- 3.58 (m, 1H), 2.39 (s, 3H), 1.74 (s, 3H). 118 [00259] [00260] Cl F CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.91 (s, 1H), 8.10-7.83 (m, 2H), 7.48 (d, J = 3.5 Hz, 1H), 6.96 (d, J = 3.5 Hz, 1H), 4.04 (d, J = 17.5 Hz, 1H), 3.65 (s, 6H), 3.64- 3.58 (m, 1H), 2.52 (s, 3H), 1.74 (s, 3H). 119 [00261] [00262] Cl F CH 120 [00263] [00264] Cl F CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.97 (d, J = 7.5 Hz, 1H), 7.93 (d, J = 9.5 Hz, 1H), 4.13 (q, J = 7.0 Hz, 2H), 3.99 (d, J = 17.5 Hz, 1H), 3.65-3.60 (m, 7H), 2.03 (s, 3H), 1.72 (s, 3H), 1.29 (t, J = 7.0 Hz, 3H). 121 [00265] [00266] Cl F CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.96 (d, J = 7.5 Hz, 1H), 7.91 (d, J = 9.5 Hz, 1H), 4.01-3.97 (m, 1H), 3.73-3.69 (m, 1H), 3.63 (s, 6H), 3.60-3.56 (m, 1H), 3.51-3.46 (m, 1H), 3.26 (s, 3H), 1.96 (s, 3H), 1.70 (s, 3H). 122 [00267] [00268] Cl F CH 123 [00269] [00270] Cl F CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.97 (d, J = 7.5 Hz, 1H), 7.92 (d, J = 9.5 Hz, 1H), 4.21 (q, J = 7.0 Hz, 2H), 3.92 (d, J = 17.5 Hz, 1H), 3.65 (s, 6H), 3.54 (d, J = 17.5 Hz, 1H), 1.94 (s, 3H), 1.64 (s, 3H), 1.26 (t, J = 7.0 Hz, 3H). 124 [00271] [00272] Cl F CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.01 (d, J = 7.5 Hz, 1H), 7.94 (d, J = 9.5 Hz, 1H), 7.83-7.76 (m, 2H), 7.60-7.48 (m, 3H), 4.07 (d, J = 17.5 Hz, 1H), 3.69-3.64 (m, 7H), 2.41 (s, 3H), 1.79 (s, 3H). 125 [00273] [00274] Cl F CH 126 [00275] [00276] Cl F CH 127 [00277] [00278] Cl F CH 128 [00279] [00280] Cl F CH 129 [00281] [00282] Cl F CH 130 [00283] [00284] Cl F CH 131 [00285] [00286] Cl F CH 132 [00287] [00288] Cl F CH 133 [00289] [00290] Cl F CH 134 [00291] [00292] Cl F CH 135 [00293] [00294] Cl F CH 136 [00295] [00296] Cl F CH 137 [00297] [00298] Cl F CH 138 [00299] [00300] Cl F CH 139 [00301] [00302] Cl F CH 140 [00303] [00304] Cl F CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.92-7.89 (m, 2H), 7.54-7.48 (m, 4H), 7.42-7.41 (m, 4H), 7.36- 7.27 (m, 2H), 3.68-3.64 (m, 7H), 3.48 (d, J = 17.5 Hz, 1H), 1.54 (s, 3H). 141 [00305] [00306] Cl F CH 142 [00307] [00308] Cl F CH 143 [00309] [00310] Cl F CH 144 [00311] [00312] Cl F CH 145 [00313] [00314] Cl F CH 146 [00315] [00316] Cl F CH .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.98 (d, J = 7.5 Hz, 1H), 7.94 (d, J = 9.5 Hz, 1H), 3.77 (s, 6H), 3.47 (d, J = 17.5 Hz, 1H), 2.82-2.75 (m, 2H), 2.39-2.29 (m, 2H), 1.42 (s, 3H), 1.14-1.00 (m, 2H), 0.83-0.70 (m, 2H). 147 [00317] [00318] Cl F CH 148 [00319] [00320] Cl F CH 149 [00321] [00322] Cl F CH 150 [00323] [00324] Cl F CH 151 [00325] [00326] Cl F CH 152 [00327] [00328] Cl F CH 153 [00329] [00330] Cl F CH 154 [00331] [00332] Cl F CH 155 [00333] [00334] Cl F CH 156 [00335] [00336] Cl F CH 157 [00337] [00338] Cl F CH 158 [00339] [00340] Cl F CH 159 [00341] [00342] Cl F CH 160 [00343] [00344] Cl F CH .sup.1H NMR (500 MHz, Chloroform-d) δ 7.32 (d, J = 9.0 Hz, 1H), 7.22 (d, J = 8.0 Hz, 1H), 6.08 (s, 1H), 3.85 (s, 3H), 3.41 (d, J = 18.0 Hz, 1H), 3.05 (d, J = 18.0 Hz, 1H), 2.66 (s, 6H), 1.50 (s, 3H). 161 [00345] [00346] Cl H CH 162 [00347] [00348] Cl Cl CH 163 [00349] [00350] Cl OH CH 164 [00351] [00352] Br F CH 165 [00353] [00354] CF.sub.3 F CH 166 [00355] [00356] CN H CH 167 [00357] [00358] CN F CH 168 [00359] [00360] NO.sub.2 F CH 169 [00361] [00362] NH.sub.2 F CH 170 [00363] [00364] Cl F N .sup.1H NMR (500 MHz, Chloroform-d) δ 7.60 (d, J = 8.0 Hz, 1H), 6.08 (s, 1H), 3.82 (s, 3H), 3.05 (d, J = 18.0 Hz, 1H), 2.82 (d, J = 18.0 Hz, 1H), 2.64 (s, 6H), 1.52 (s, 3H). 171 [00365] [00366] Cl H N 172 [00367] [00368] CN H N 173 [00369] [00370] Cl F CH 174 [00371] [00372] Cl F CH 175 [00373] [00374] Cl F CH 176 [00375] [00376] Cl F CH 177 [00377] [00378] Cl F CH 178 [00379] [00380] Cl F CH 179 [00381] [00382] Cl F CH 180 [00383] [00384] Cl F CH 181 [00385] [00386] Cl F CH 182 [00387] [00388] Cl F CH 183 [00389] [00390] Cl F CH 184 [00391] [00392] Cl F CH 185 [00393] [00394] Cl F CH 186 [00395] [00396] Cl F CH 187 [00397] [00398] Cl F CH 188 [00399] [00400] Cl F CH 189 [00401] [00402] Cl F CH 190 [00403] [00404] Cl F CH 191 [00405] [00406] Cl F CH 192 [00407] [00408] Cl F CH 193 [00409] [00410] Cl F CH 194 [00411] [00412] Cl F CH 195 [00413] [00414] Cl F CH 196 [00415] [00416] Cl F CH 197 [00417] [00418] Cl F CH .sup.1H NMR (500 MHz, Chloroform-d) δ 7.30 (d, J = 9.0 Hz, 1H), 6.96 (d, J = 8.0 Hz, 1H), 6.39 (s, 1H), 3.86 (s, 3H), 3.33 (d, J = 18.0 Hz, 1H), 3.08 (d, J = 18.0 Hz, 1H), 2.61 (s, 6H), 1.65 (s, 3H). 198 [00419] [00420] Cl F CH 199 [00421] [00422] Cl F CH 200 [00423] [00424] Cl F CH 201 [00425] [00426] Cl F CH 202 [00427] [00428] Cl F CH 203 [00429] [00430] Cl F CH 204 [00431] [00432] Cl F CH 205 [00433] [00434] Cl F CH 206 [00435] [00436] Cl F CH 207 [00437] [00438] Cl F CH 208 [00439] [00440] Cl F CH 209 [00441] [00442] Cl F CH 210 [00443] [00444] Cl F CH 211 [00445] [00446] Cl F CH 212 [00447] [00448] Cl F CH 213 [00449] [00450] Cl F CH 214 [00451] [00452] Cl F CH 215 [00453] [00454] Cl F CH 216 [00455] [00456] Cl F CH 217 [00457] [00458] Cl F CH 218 [00459] [00460] Cl F CH .sup.1H NMR (500 MHz, Chloroform-d) δ 7.33 (d, J = 9.0 Hz, 1H), 7.06 (d, J = 8.0 Hz, 1H), 6.49 (s, 1H), 4.21 (s, 3H), 3.39 (d, J = 18.0 Hz, 1H), 3.05 (d, J = 18.0 Hz, 1H), 2.63 (s, 6H), 1.62 (s, 3H). 219 [00461] [00462] Cl F CH

[0132] 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.

[0133] 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.

[0134] Examples of representative compounds are as follows, the synthesis methods of other compounds are similar, and will not be described in detail here.

[0135] 1. Synthesis of Compound 10

[0136] 1) 10-1 (20 g, 98.3 mmol, 1.0 eq) was added to 200 ml of EtOH, then NH.sub.2OH HCl (7.5 g, 108.1 mmol, 1.1 eq) aqueous solution (30 ml) was added dropwise to the reaction solution at 0° C. After the dropwise addition was completed, the reaction solution was stirred at 0° C. for 3 hours. When the raw material was almost completely reacted by LCMS detection, a major new peak emerged. The reaction solution was concentrated to remove part of ethanol, then poured into 100 ml of water, the solid was precipitated, filtered, the filter cake was washed with water, then dried to produce 10-2 (20 g, 93% yield) (white solid).

##STR00463##

[0137] 2) 10-2 (20 g, 91.5 mmol, 1.0 eq) was added to 150 ml of DMF, then NCS (13.4 g, 100.7 mmol, 1.1 eq) was slowly added to the reaction solution at 35° C. After the addition was completed, the reaction solution was stirred at 35° C. for 1.5 hours. The raw material was almost completely reacted by LCMS detection. The reaction solution was poured into 100 ml of HCl (1M), then extracted by adding dichloromethane. The organic phase was washed with saturated brine (100 ml*3), then concentrated to produce crude product 10-3 (26 g, crude product) (yellow oily). Such crude product was directly used in the next step.

##STR00464##

[0138] 3) 10-3 (26 g) and Et.sub.3N (15.6 g, 154.1 mmol, 1.5 eq) were added to 200 ml of DCM. Then, the reaction solution was added with 10-4 (14.1 g, 123.3 mmol, 1.2 eq) at 0° C. The product was detected by LCMS detection after the reaction solution was reacted at 0° C. for 1 hour. The reaction solution was added with 100 ml of water and extracted with dichloromethane (100 ml*3). The organic phase was dried with anhydrous sodium sulfate and concentrated. The crude product was purified by column chromatography to produce 10-5 (17 g, 50% yield) (yellow solid.

##STR00465##

[0139] 4) 10-5 (17 g, 51.4 mmol, 1.0 eq), Fe powder (8.6 g, 154.2 mmol, 3 eq), NH.sub.4Cl (5.5 g, 102.8 mmol, 2 eq) and water (50 ml) were added to 200 ml of EtOH in sequence. After the reaction solution was reacted at 80° C. for 2 hours, the raw material disappeared by LCMS detection, and the principal peak was the product peak. The reaction solution was filtered with diatomite, then concentrated to remove ethanol and added with water (100 ml), extracted with ethyl acetate, then concentrated to produce black crude product. Such crude product was separated and purified by column chromatography to produce 10-6 (12 g, 76.6% yield) (yellow solid).

##STR00466##

[0140] 5) 10-6 (0.6 g, 2.0 mmol, 1.0 eq) and phenyl chloroformate (0.34 g, 2.2 mmol, 1.1 eq) were added to 10 ml of toluene, then the reaction solution was heated at 110° C. for 1 hour. The raw material was almost completely reacted by LCMS detection, and the principal peak belonged to the product. The solvent was concentrated and the crude product was separated by column chromatography to produce 10-7 (0.7 g, 83.4% yield) (white solid).

##STR00467##

[0141] 6) a (0.48 g, 2.1 mmol, 1.5 eq) and AcONa (58 mg, 0.7 mmol, 0.5 eq) were added to 10 ml of DMF. Then, the reaction solution was added with 10-7 (0.6 g, 1.4 mmol, 1.0 eq) at 60° C., and reacted at 60° C. for 1 hour. The product was detected by LCMS detection. The reaction solution was added with 10 ml of water, then extracted with ethyl acetate. After the organic phase was washed with saturated salt brine (20 ml*1) and concentrated, the crude product was separated by column chromatography to produce 10-8 (0.4 g, 61.4% yield) (white solid).

##STR00468##

[0142] 7) 10-8 (10 g, 21.9 mmol, 1.0 eq) and HBr (50 ml) were added to 50 ml of 1,4-dioxane, then the reaction solution was reacted at 80° C. for 6 hours. The product was detected by LCMS detection. The reaction solution was added with 50 ml of water, then extracted with ethyl acetate (50 ml*3). The organic phase was dried with anhydrous sodium sulfate, then concentrated to produce 10-9 (8.5 g, 90.6% yield) (yellow solid).

##STR00469##

[0143] 8) 10-9 (0.5 g, 1.17 mmol, 1.0 eq), b (0.10 g, 1.40 mmol, 1.2 eq), Et.sub.3N (0.14 g, 1.40 mmol, 1.2 eq) and PyBOP (0.67 g, 1.28 mmol, 1.1 eq) were added to 8 ml of DCM in sequence. After the reaction solution was reacted at 25° C. for 2 hours, the raw material disappeared by LCMS detection, and the principal peak was the product peak. The reaction solution was added with 10 ml of water and extracted with dichloromethane (10 ml*2). The organic phase was dried with anhydrous sodium sulfate, then concentrated to produce crude product. Such crude product was separated and purified by column chromatography to produce compound 10 (0.47 g, 83.3% yield) (yellow solid).

##STR00470##

[0144] 2. Synthesis of Compound 124

[0145] Compound 10-9 was prepared by referring to the above method. 10-9 (0.5 g, 1.17 mmol, 1.0 eq), c (0.19 g, 1.40 mmol, 1.2 eq), Et.sub.3N (0.14 g, 1.40 mmol, 1.2 eq) and PyBOP (0.67 g, 1.28 mmol, 1.1 eq) were added into 8 ml of DCM in sequence. After reaction solution was reacted at 25° C. for 2 hours, the raw material disappeared by LCMS detection, and the principal peak was the product peak. The reaction solution was added with 10 ml of water, then extracted with dichloromethane (10 ml*2). The organic phase was dried with anhydrous sodium sulfate, then concentrated to produce crude product. Such crude product was separated and purified by column chromatography to produce compound 124 (0.50 g, 78.5% yield) (yellow solid).

##STR00471##

[0146] Biological Activity Evaluation:

[0147] The activity level criteria for plant damage (i.e., growth control rate) are as follows:

[0148] Level 5: growth control rate is above 85%;

[0149] Level 4: growth control rate is greater than or equal to 60% and less than 85%;

[0150] Level 3: growth control rate is greater than or equal to 40% and less than 60%;

[0151] Level 2: growth control rate is greater than or equal to 20% and less than 40%;

[0152] Level 1: growth control rate is greater than or equal to 5% and less than 20%;

[0153] Level 0: growth control rate is less than 5%.

[0154] The above growth control rates are fresh weight control rates.

[0155] Experiment on weeding effect in post-emergence stage:

[0156] 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 trolia, Scirpus juncoides, Cyperus rotundus, Cyperus iria, Cyperus difformis, Elmbristylis, 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 2.

TABLE-US-00002 TABLE 2 Results on weeding effect in post-emergence stage Veronica Compound Echinochloa Digitaria Setaria Leptochloa Eleusine didyma Galium Abutilon Amaranthus Dose No. crusgalli sanguinalis viridis chinensis indica Tenore aparine theophrasti retroflexus (g a.i./ha) 2 5 5 5 5 5 5 5 5 5 15 10 5 5 5 5 5 5 5 5 5 15 16 5 5 5 5 5 5 5 5 5 15 54 5 5 5 5 5 5 5 5 5 15 56 5 5 5 5 5 5 5 5 5 15 57 5 5 5 5 5 5 5 5 5 15 58 5 5 5 5 5 5 5 5 5 15 59 5 5 5 5 5 5 5 5 5 15 60 5 5 5 5 5 5 5 5 5 15 61 5 5 5 5 5 5 5 5 5 15 67 5 5 5 5 5 5 5 5 5 15 68 5 5 5 5 5 5 5 5 5 15 69 5 5 5 5 5 5 5 5 5 15 70 5 5 5 5 5 5 5 5 5 15 71 5 5 5 5 5 5 5 5 5 15 74 5 5 5 5 5 5 5 5 5 15 75 5 5 5 5 5 5 5 5 5 15 79 5 5 5 5 5 5 5 5 5 15 80 5 5 5 5 5 5 5 5 5 15 81 5 5 5 5 5 5 5 5 5 15 83 5 5 5 5 5 5 5 5 5 15 84 5 5 5 5 5 5 5 5 5 15 90 5 5 5 5 5 5 5 5 5 15 117 5 5 5 5 5 5 5 5 5 15 118 5 5 5 5 5 5 5 5 5 15 120 5 5 5 5 5 5 5 5 5 15 121 5 5 5 5 5 5 5 5 5 15 123 5 5 5 5 5 5 5 5 5 15 124 5 5 5 5 5 5 5 5 5 15 140 5 5 5 5 5 5 5 5 5 15 146 5 5 5 5 5 5 5 5 5 15 160 5 5 5 5 5 5 5 5 5 15 170 5 5 5 5 5 5 5 5 5 15 197 5 5 5 5 5 5 5 5 5 15 218 5 5 5 5 5 5 5 5 5 15

[0157] Experiment on weed effect in pre-emergence stage:

[0158] 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.

[0159] 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 L., and Cyperus rotundus L., etc., and have excellent commercial value.

[0160] Transplanted rice safety evaluation and weed control effect evaluation in rice field:

[0161] 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.

[0162] 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.

[0163] 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.

[0164] Note: The seeds of Echinochloa crusgalli, Scirpus juncoides and Bidens tripartita L., and Sagittaria trifolia were collected from Heilongjiang Province of China. The tests indicated that the weeds were resistant to the common doses of Pyrazosulfuron-ethyl.

[0165] 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.