N-(1,3,4-OXADIAZOL-2-YL)ARYLCARBOXAMIDES OR SALTS THEREOF, PREPARATION METHODS, HERBICIDAL COMPOSITIONS AND USES THEREOF

Abstract

The invention belongs to the technical field of agricultural chemicals, and particularly relates to an N-(1,3,4-oxadiazol-2-yl)arylcarboxamide compound or a salt thereof, a preparation method, a herbicidal composition and a use thereof. The compound is as shown in the following Formula I:

##STR00001## wherein X represents O, S, SO, SO.sub.2 or NR.sub.1; Y represents halogen, cyano, cyanoalkyl, carboxyl, nitro, etc.; or —X—Y represents unsubstituted or substituted five- or six-membered heterocyclyl or heteroaryl; Z represents hydrogen, halogen, cyano, OR.sub.4, -alkyl-OR.sub.4, —O-alkyl-N(R.sub.5).sub.2, etc., M represents hydrogen, OR.sub.6, SR.sub.6, COR.sub.6, COOR.sub.6, CON(R.sub.7).sub.2, etc. The compound has advantages of a low dosage for use, excellent herbicidal activity, and higher crop safety, especially good selectivity for key crops such as rice.

Claims

1. An N-(1,3,4-oxadiazol-2-yl)arylcarboxamide compound represented by Formula I or a salt thereof, ##STR00876## wherein, X represents O, S, SO, SO.sub.2 or NR.sub.1; Y represents halogen, cyano, cyanoalkyl, carboxy, nitro, N(R.sub.2).sub.2, -alkyl-N(R.sub.2).sub.2, CON(R.sub.2).sub.2, -alkyl-CON(R.sub.2).sub.2, -alkyl-N(R.sub.2).sub.3.sup.+I.sup.−, hydroxyalkyl, alkyl substituted by amino and carboxy, OR.sub.3, SR.sub.3, -alkyl-SOR.sub.3, -alkyl-OR.sub.3, -alkyl-SR.sub.3, COR.sub.3, COOR.sub.3, -alkyl-COR.sub.4, -alkyl-COOR.sub.4, -alkyl-OCOR.sub.3, Si(R.sub.3).sub.3, -alkyl-O—Si(R.sub.3).sub.3, -alkyl-O—N═C(R.sub.3).sub.2, alkyl, haloalkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted cycloalkylalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heterocyclylalkyl, unsubstituted or substituted arylalkyl, or unsubstituted or substituted heteroarylalkyl, wherein the substituted alkenyl or the substituted alkynyl is alkenyl or alkynyl substituted by at least one group selected from the group consisting of halogen, cyano, cycloalkyl, alkylcarbonyl, alkoxycarbonyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, and trialkylsilyl; or, —X—Y represents an unsubstituted or substituted five- or six-membered heterocyclyl or heteroaryl, wherein the heterocyclyl or heteroaryl contains, besides C atom and N atom at 1-position, 0 to 3 of the following atoms or groups as a component of the ring: O, N, NR.sub.1, SO.sub.2, C═O; Z represents hydrogen, halogen, cyano, OR.sub.4, -alkyl-OR.sub.4, —O-alkyl-N(R.sub.5).sub.2, -alkyl-O-alkyl-N(R.sub.5).sub.2, N(R.sub.5).sub.2, -alkyl-(C═O).sub.m—N(R.sub.5).sub.2, —NH-alkyl-N(R.sub.5).sub.2, halogen-free or halogen-containing alkyl, halogen-free or halogen-containing alkenyl, halogen-free or halogen-containing alkynyl, halogen-free or halogen-containing alkoxycarbonyl, halogen-free or halogen-containing alkoxycarbonylalkyl, halogen-free or halogen-containing alkylcarbonyl, halogen-free or halogen-containing alkylcarbonylalkyl, halogen-free or halogen-containing alkylcarbonyloxyalkyl, halogen-free or halogen-containing alkylthio, halogen-free or halogen-containing alkylsulfinyl, halogen-free or halogen-containing alkylsulfonyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heterocyclylalkyl, unsubstituted or substituted arylalkyl, unsubstituted or substituted heteroarylalkyl, unsubstituted or substituted heterocyclylcarbonylalkyl, unsubstituted or substituted arylcarbonylalkyl, unsubstituted or substituted heteroarylcarbonylalkyl, unsubstituted or substituted heterocyclylcarbonyloxyalkyl, unsubstituted or substituted arylcarbonyloxyalkyl, or unsubstituted or substituted heteroarylcarbonyloxyalkyl; M represents hydrogen, OR.sub.6, SR.sub.6, COR.sub.6, COOR.sub.6, OCOR.sub.6, CON(R.sub.7).sub.2, N(R.sub.7).sub.2, NR.sub.8COOR.sub.6, NR.sub.8CON(R.sub.7).sub.2, -alkyl-R, halogen-free or halogen-containing alkyl, halogen-free or halogen-containing alkenyl, halogen-free or halogen-containing alkynyl, halogen-free or halogen-containing cycloalkyl, unsubstituted or substituted arylalkyl, or unsubstituted or substituted heteroarylalkyl; R represents halogen-free or halogen-containing alkenyl, halogen-free or halogen-containing alkynyl, halogen-free or halogen-containing cycloalkyl, CN, OR.sub.11, OCOR.sub.11, COOR.sub.11, COR.sub.11, —O—(C═O)—O—R.sub.11, OSO.sub.2R.sub.12, SO.sub.2OR.sub.11, —S(O).sub.nR.sub.12, N(R.sub.13).sub.2, CON(R.sub.13).sub.2, SO.sub.2N(R.sub.13).sub.2, NR.sub.14COR.sub.11, NR.sub.14SO.sub.2R.sub.12, —O—(C═O)—N(R.sub.13).sub.2; R.sub.4, R.sub.6, and R.sub.11 each independently represent hydrogen, halogen-free or halogen-containing alkyl, halogen-free or halogen-containing alkenyl, halogen-free or halogen-containing alkynyl, halogen-free or halogen-containing cycloalkyl, halogen-free or halogen-containing cycloalkylalkyl, halogen-free or halogen-containing cycloalkenyl, halogen-free or halogen-containing alkoxyalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted heterocyclylalkyl, unsubstituted or substituted heterocyclyloxyalkyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl, unsubstituted or substituted aryloxyalkyl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heteroarylalkyl, or unsubstituted or substituted heteroaryloxyalkyl; R.sub.3 and R.sub.12 each independently represent halogen-free or halogen-containing alkyl, halogen-free or halogen-containing alkenyl, halogen-free or halogen-containing alkynyl, halogen-free or halogen-containing cycloalkyl, halogen-free or halogen-containing cycloalkylalkyl, halogen-free or halogen-containing cycloalkenyl, halogen-free or halogen-containing alkoxyalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted heterocyclylalkyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl, unsubstituted or substituted heteroaryl, or unsubstituted or substituted heteroarylalkyl; R.sub.1, R.sub.2, R.sub.5, R.sub.7, R.sub.8, R.sub.13, and R.sub.14 each independently represent hydrogen, nitro, alkoxyaminocarbonyl, trialkylsilyl, dialkylphosphonyl, N(R.sub.21).sub.2, CON(R.sub.21).sub.2, OR.sub.21, COR.sub.21, CO.sub.2R.sub.21, COSR.sub.21, OCOR.sub.21, S(O).sub.rR.sub.22, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, cycloalkenyl, halocycloalkyl, alkoxyalkyl, cycloalkylalkyl, aryl, arylalkyl, aryloxy, aryloxyalkyl, arylalkyloxy, arylcarbonyl, aryl sulfonyl, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroaryloxyalkyl, heteroarylalkyloxy, heteroarylcarbonyl, heteroarylsulfonyl, heterocyclyl, heterocyclylalkyl, heterocyclyloxy, heterocyclyloxyalkyl, heterocyclylalkyloxy, heterocyclylcarbonyl, heterocyclylsulfonyl, aryl-NR.sub.21-alkyl, heteroaryl-NR.sub.21-alkyl, heterocyclyl-NR.sub.21-alkyl, wherein the last 35 groups as mentioned are each substituted by 0, 1, 2 or 3 groups selected from the group consisting of: cyano, halogen, nitro, cyanothio, OR.sub.21, S(O).sub.rR.sub.22, N(R.sub.21).sub.2, NR.sub.21OR.sub.21, COR.sub.21, OCOR.sub.21, SCOR.sub.22, NR.sub.21COR.sub.21, NR.sub.21SO.sub.2R.sub.22, CO.sub.2R.sub.21, COSR.sub.21, CON(R.sub.21).sub.2 and alkoxyalkoxycarbonyl; R.sub.21 independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl; R.sub.22 independently represents alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl; m represents 0 or 1; n and r each independently represent 0, 1 or 2; and when X represents S or SO, Y is not methyl.

2. The N-(1,3,4-oxadiazol-2-yl)arylcarboxamide compound or a salt thereof according to claim 1, wherein X represents O, S, SO, SO.sub.2 or NR.sub.1; Y represents halogen, cyano, cyano-(C.sub.1-C.sub.8)alkyl, carboxy, nitro, N(R.sub.2).sub.2, —(C.sub.1-C.sub.8)alkyl-N(R.sub.2).sub.2, CON(R.sub.2).sub.2, —(C.sub.1-C.sub.8)alkyl-CON(R.sub.2).sub.2, —(C.sub.1-C.sub.8)alkyl-N(R.sub.2).sub.3.sup.+I.sup.−, hydroxy(C.sub.1-C.sub.8)alkyl, (C.sub.1-C.sub.8)alkyl substituted by amino and carboxy, OR.sub.3, SR.sub.3, —(C.sub.1-C.sub.8)alkyl-SOR.sub.3, —(C.sub.1-C.sub.8)alkyl-OR.sub.3, —(C.sub.1-C.sub.8)alkyl-SR.sub.3, COR.sub.3, COOR.sub.3, —(C.sub.1-C.sub.8)alkyl-COR.sub.4, —(C.sub.1-C.sub.8)alkyl-COOR.sub.4, —(C.sub.1-C.sub.8)alkyl-OCOR.sub.3, Si(R.sub.3).sub.3, —(C.sub.1-C.sub.8)alkyl-O—Si(R.sub.3).sub.3, —(C.sub.1-C.sub.8)alkyl-O—N═C(R.sub.3).sub.2, C.sub.1-C.sub.8alkyl, halo C.sub.1-C.sub.8 alkyl; unsubstituted or substituted C.sub.2-C.sub.8 alkenyl, unsubstituted or substituted C.sub.2-C.sub.8 alkynyl, unsubstituted or substituted C.sub.3-C.sub.8 cycloalkyl, unsubstituted or substituted C.sub.3-C.sub.8 cycloalkyl C.sub.1-C.sub.8 alkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heterocyclyl C.sub.1-C.sub.8 alkyl, unsubstituted or substituted aryl C.sub.1-C.sub.8 alkyl, unsubstituted or substituted heteroaryl C.sub.1-C.sub.8 alkyl, wherein the substituted C.sub.2-C.sub.8 alkenyl or the substituted C.sub.2-C.sub.8 alkynyl is C.sub.2-C.sub.8 alkenyl or C.sub.2-C.sub.8 alkynyl substituted by at least one group selected from the group consisting of halogen, cyano, C.sub.3-C.sub.8 cycloalkyl, C.sub.1-C.sub.8 alkylcarbonyl, C.sub.1-C.sub.8 alkoxycarbonyl, C.sub.1-C.sub.8 alkoxy, C.sub.1-C.sub.8 alkylthio, C.sub.1-C.sub.8 alkylsulfinyl, C.sub.1-C.sub.8 alkylsulfonyl and tri(C.sub.1-C.sub.8)alkylsilyl, the substituted C.sub.3-C.sub.8 cycloalkyl or the substituted (C.sub.3-C.sub.8)cycloalkyl(C.sub.1-C.sub.8)alkyl is C.sub.3-C.sub.8 cycloalkyl or (C.sub.3-C.sub.8)cycloalkyl(C.sub.1-C.sub.8)alkyl substituted by at least one group selected from the group consisting of C.sub.1-C.sub.8 alkyl, halogen and phenyl; or, —X—Y represents ##STR00877## which is unsubstituted or substituted by at least one group selected from the group consisting of halogen, nitro, cyano, hydroxy, carboxy, amino, thiol, formyl, unsubstituted or substituted phenyl, unsubstituted or substituted benzyl, unsubstituted or substituted phenoxy, halogen-free or halogen-containing alkyl, halogen-free or halogen-containing alkenyl, halogen-free or halogen-containing alkynyl, halogen-free or halogen-containing cycloalkyl, halogen-free or halogen-containing cycloalkylalkyl, halogen-free or halogen-containing alkoxy, halogen-free or halogen-containing alkylthio, halogen-free or halogen-containing alkoxyalkyl, halogen-free or halogen-containing alkylthioalkyl, halogen-free or halogen-containing alkylcarbonyl, halogen-free or halogen-containing alkoxycarbonyl, halogen-free or halogen-containing alkylsulfinyl, halogen-free or halogen-containing alkylsulfonyl, halogen-free or halogen-containing alkylamino, halogen-free or halogen-containing dialkylamino, halogen-free or halogen-containing alkylacyloxy, wherein the substituted phenyl, the substituted benzyl or the substituted phenoxy is phenyl, benzyl or phenoxy substituted by at least one group selected from the group consisting of halogen, alkyl and alkoxy; Z represents hydrogen, halogen, cyano, OR.sub.4, —(C.sub.1-C.sub.8)alkyl-OR.sub.4, —O—(C.sub.1-C.sub.8)alkyl-N(R.sub.5).sub.2, —(C.sub.1-C.sub.8)alkyl-O—(C.sub.1-C.sub.8)alkyl-N(R.sub.5).sub.2, N(R.sub.5).sub.2, —(C.sub.1-C.sub.8)alkyl-(C═O).sub.m—N(R.sub.5).sub.2, —NH—(C.sub.1-C.sub.8)alkyl-N(R.sub.5).sub.2, halogen-free or halogen-containing C.sub.1-C.sub.8 alkyl, halogen-free or halogen-containing C.sub.2-C.sub.8 alkenyl, halogen-free or halogen-containing C.sub.2-C.sub.8 alkynyl, halogen-free or halogen-containing C.sub.1-C.sub.8alkoxy carbonyl, halogen-free or halogen-containing C.sub.1-C.sub.8alkoxycarbonyl C.sub.1-C.sub.8alkyl, halogen-free or halogen-containing C.sub.1-C.sub.8alkyl carbonyl, halogen-free or halogen-containing C.sub.1-C.sub.8alkyl carbonyl C.sub.1-C.sub.8alkyl, halogen-free or halogen-containing C.sub.1-C.sub.8alkyl carbonyloxy C.sub.1-C.sub.8alkyl, halogen-free or halogen-containing C.sub.1-C.sub.8 alkylthio, halogen-free or halogen-containing C.sub.1-C.sub.8alkylsulfinyl, halogen-free or halogen-containing C.sub.1-C.sub.8alkylsulfonyl, unsubstituted or substituted C.sub.3-C.sub.8 cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heterocyclyl C.sub.1-C.sub.8alkyl, unsubstituted or substituted aryl C.sub.1-C.sub.8alkyl, unsubstituted or substituted heteroaryl C.sub.1-C.sub.8alkyl, unsubstituted or substituted heterocyclylcarbonyl C.sub.1-C.sub.8alkyl, unsubstituted or substituted arylcarbonyl C.sub.1-C.sub.8alkyl, unsubstituted or substituted heteroarylcarbonyl C.sub.1-C.sub.8alkyl, unsubstituted or substituted heterocyclylcarbonyloxy C.sub.1-C.sub.8alkyl, unsubstituted or substituted arylcarbonyloxy C.sub.1-C.sub.8alkyl, or unsubstituted or substituted heteroarylcarbonyloxy C.sub.1-C.sub.8alkyl, wherein the substituted C.sub.3-C.sub.8 cycloalkyl is C.sub.3-C.sub.8 cycloalkyl substituted by at least one group selected from the group consisting of C.sub.1-C.sub.8 alkyl, halogen and phenyl; M represents hydrogen, OR.sub.6, SR.sub.6, COR.sub.6, COOR.sub.6, OCOR.sub.6, CON(R.sub.7).sub.2, N(R.sub.7).sub.2, NR.sub.8COOR.sub.6, NR.sub.8CON(R.sub.7).sub.2, —(C.sub.1-C.sub.8)alkyl-R, halogen-free or halogen-containing C.sub.1-C.sub.8alkyl, halogen-free or halogen-containing C.sub.2-C.sub.8alkenyl, halogen-free or halogen-containing C.sub.2-C.sub.8alkynyl, halogen-free or halogen-containing C.sub.3-C.sub.8cycloalkyl, unsubstituted or substituted aryl C.sub.1-C.sub.8alkyl, or unsubstituted or substituted heteroaryl C.sub.1-C.sub.8 alkyl; R represents halogen-free or halogen-containing C.sub.2-C.sub.8alkenyl, halogen-free or halogen-containing C.sub.2-C.sub.8alkynyl, halogen-free or halogen-containing C.sub.3-C.sub.8cycloalkyl, CN, OR.sub.11, OCOR.sub.11, COOR.sub.11, COR.sub.11, —O—(C═O)—O—R.sub.11, OSO.sub.2R.sub.12, SO.sub.2OR.sub.11, —S(O).sub.nR.sub.12, N(R.sub.13).sub.2, CON(R.sub.13).sub.2, SO.sub.2N(R.sub.13).sub.2, NR.sub.14COR.sub.11, NR.sub.14SO.sub.2R.sub.12, —O—(C═O)—N(R.sub.13).sub.2; R.sub.4, R.sub.6 and Ru each independently represent hydrogen, halogen-free or halogen-containing C.sub.1-C.sub.8alkyl, halogen-free or halogen-containing C.sub.2-C.sub.8alkenyl, halogen-free or halogen-containing C.sub.2-C.sub.8alkynyl, halogen-free or halogen-containing C.sub.3-C.sub.8cycloalkyl, halogen-free or halogen-containing C.sub.3-C.sub.8cycloalkyl C.sub.1-C.sub.8alkyl, halogen-free or halogen-containing C.sub.3-C.sub.8cycloalkenyl, halogen-free or halogen-containing C.sub.1-C.sub.8alkoxy C.sub.1-C.sub.8alkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted heterocyclyl C.sub.1-C.sub.8alkyl, unsubstituted or substituted heterocyclyloxy C.sub.1-C.sub.8alkyl, unsubstituted or substituted aryl, unsubstituted or substituted aryl C.sub.1-C.sub.8alkyl, unsubstituted or substituted aryloxy C.sub.1-C.sub.8alkyl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heteroaryl C.sub.1-C.sub.8alkyl, unsubstituted or substituted heteroaryloxy C.sub.1-C.sub.8alkyl; R.sub.3 and R.sub.12 each independently represent halogen-free or halogen-containing C.sub.1-C.sub.8alkyl, halogen-free or halogen-containing C.sub.2-C.sub.8alkenyl, halogen-free or halogen-containing C.sub.2-C.sub.8alkynyl, halogen-free or halogen-containing C.sub.3-C.sub.8cycloalkyl, halogen-free or halogen-containing C.sub.3-C.sub.8cycloalkyl C.sub.1-C.sub.8alkyl, halogen-free or halogen-containing C.sub.3-C.sub.8cycloalkenyl, halogen-free or halogen-containing C.sub.1-C.sub.8alkoxy C.sub.1-C.sub.8alkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted heterocyclyl C.sub.1-C.sub.8alkyl, unsubstituted or substituted aryl, unsubstituted or substituted aryl C.sub.1-C.sub.8alkyl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heteroaryl C.sub.1-C.sub.8alkyl; R.sub.1, R.sub.2, R.sub.5, R.sub.7, R.sub.8, R.sub.13, and R.sub.14 each independently represent hydrogen, nitro, alkoxyaminocarbonyl, trialkylsilyl, dialkylphosphonyl, N(R.sub.21).sub.2, CON(R.sub.21).sub.2, OR.sub.21, COR.sub.21, CO.sub.2R.sub.21, COSR.sub.21, OCOR.sub.21, S(O).sub.rR.sub.22, C.sub.1-C.sub.8alkyl, haloC.sub.1-C.sub.8alkyl, C.sub.2-C.sub.8alkenyl, haloC.sub.2-C.sub.8alkenyl, C.sub.2-C.sub.8alkynyl, haloC.sub.2-C.sub.8alkynyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.8cycloalkenyl, haloC.sub.3-C.sub.8cycloalkyl, C.sub.1-C.sub.8alkoxy C.sub.1-C.sub.8alkyl, C.sub.3-C.sub.8cycloalkyl C.sub.1-C.sub.8alkyl, aryl, aryl C.sub.1-C.sub.8alkyl, aryloxy, aryloxy C.sub.1-C.sub.8alkyl, aryl C.sub.1-C.sub.8alkyloxy, arylcarbonyl, aryl sulfonyl, heteroaryl, heteroaryl C.sub.1-C.sub.8alkyl, heteroaryloxy, heteroaryloxy C.sub.1-C.sub.8alkyl, heteroaryl C.sub.1-C.sub.8alkyloxy, heteroarylcarbonyl, heteroarylsulfonyl, heterocyclyl, heterocyclyl C.sub.1-C.sub.8alkyl, heterocyclyloxy, heterocyclyloxy C.sub.1-C.sub.8alkyl, heterocyclyl C.sub.1-C.sub.8alkyloxy, heterocyclylcarbonyl, heterocyclylsulfonyl, aryl-NR.sub.21—(C.sub.1-C.sub.8)alkyl, heteroaryl-NR.sub.21—(C.sub.1-C.sub.8)alkyl, or heterocyclyl-NR.sub.21—(C.sub.1-C.sub.8)alkyl, wherein the last 35 groups as mentioned each are independently substituted by 0, 1, 2 or 3 groups selected from the group consisting of cyano, halogen, nitro, cyanothio, OR.sub.21, S(O).sub.rR.sub.22, N(R.sub.21).sub.2, NR.sub.21OR.sub.21, COR.sub.21, OCOR.sub.21, SCOR.sub.22, NR.sub.21COR.sub.21, NR.sub.21SO.sub.2R.sub.22, CO.sub.2R.sub.21, COSR.sub.21, CON(R.sub.21).sub.2 and C.sub.1-C.sub.8alkoxy C.sub.1-C.sub.8alkoxycarbonyl; R.sub.21 independently represents hydrogen, C.sub.1-C.sub.8alkyl, C.sub.2-C.sub.8alkenyl, C.sub.2-C.sub.8alkynyl, C.sub.3-C.sub.8cycloalkyl, or C.sub.3-C.sub.8cycloalkyl C.sub.1-C.sub.8alkyl; R.sub.22 independently represents C.sub.1-C.sub.8alkyl, C.sub.2-C.sub.8alkenyl, C.sub.2-C.sub.8alkynyl, C.sub.3-C.sub.8cycloalkyl, or C.sub.3-C.sub.8cycloalkyl C.sub.1-C.sub.8alkyl; m represents 0 or 1; n and r each independently represent 0, 1 or 2; wherein, the “heterocyclyl” refers to ##STR00878## which has 0, 1 or 2 oxo groups; the “aryl” refers to phenyl or naphthyl, the “heteroaryl” refers to ##STR00879## ##STR00880## wherein the heterocyclyl, the aryl or the heteroaryl is unsubstituted or substituted by at least one group selected from the group consisting of halogen, nitro, cyano, cyanothio, hydroxy, carboxy, thiol, formyl, unsubstituted or substituted phenyl, unsubstituted or substituted benzyl, unsubstituted or substituted phenoxy, halogen-free or halogen-containing alkyl, halogen-free or halogen-containing alkenyl, halogen-free or halogen-containing alkynyl, halogen-free or halogen-containing cycloalkyl, halogen-free or halogen-containing cycloalkylalkyl, halogen-free or halogen-containing OR″, halogen-free or halogen-containing SR″, halogen-free or halogen-containing -alkyl-OR″, halogen-free or halogen-containing -alkyl-SR″, halogen-free or halogen-containing COR″, halogen-free or halogen-containing COOR″, halogen-free or halogen-containing COSR″, halogen-free or halogen-containing SOR″, halogen-free or halogen-containing SO.sub.2R″, halogen-free or halogen-containing OCOR″, halogen-free or halogen-containing SCOR″, substituted amino, substituted aminocarbonyl, —OCH.sub.2CH.sub.2—, —OCH.sub.2O—, and —OCH.sub.2CH.sub.2O—, wherein the substituted phenyl, the substituted benzyl or the substituted phenoxy is phenyl, benzyl or phenoxy substituted with at least one group selected from the group consisting of halogen, alkyl and alkoxy, the substituted amino or the substituted aminocarbonyl is amino or aminocarbonyl substituted by one or two groups selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, COR″, SO.sub.2R″, and OR″; R′ independently represents hydrogen, nitro, hydroxy, amino, halogen-containing or halogen-free alkyl, halogen-containing or halogen-free alkenyl, halogen-containing or halogen-free alkynyl, halogen-containing or halogen-free cycloalkyl, halogen-containing or halogen-free cycloalkenyl, halogen-containing or halogen-free cycloalkylalkyl, halogen-containing or halogen-free alkoxy, halogen-containing or halogen-free alkenyloxy, halogen-containing or halogen-free alkynyloxy, halogen-containing or halogen-free cycloalkyloxy, halogen-containing or halogen-free alkoxyalkyl, halogen-containing or halogen-free alkoxycarbonyl, halogen-containing or halogen-free alkylthiocarbonyl, halogen-containing or halogen-free alkylsulfonyl, halogen-containing or halogen-free alkylsulfonylalkyl, halogen-containing or halogen-free alkylcarbonyl, halogen-containing or halogen-free alkylcarbonylalkyl, halogen-containing or halogen-free alkylacyloxy, halogen-containing or halogen-free alkylamino, halogen-containing or halogen-free alkylaminocarbonyl, halogen-containing or halogen-free alkoxyaminocarbonyl, halogen-containing or halogen-free alkoxycarbonylalkyl, halogen-containing or halogen-free alkylaminocarbonylalkyl, halogen-containing or halogen-free trialkylsilyl, or halogen-containing or halogen-free dialkylphosphonyl; R″ independently represents hydrogen, halogen-containing or halogen-free alkyl, halogen-containing or halogen-free alkenyl, halogen-containing or halogen-free alkynyl, halogen-containing or halogen-free cycloalkyl, or halogen-containing or halogen-free cycloalkylalkyl.

3. The N-(1,3,4-oxadiazol-2-yl)arylcarboxamide compound or a salt thereof according to claim 1, wherein X represents O, S, SO, SO.sub.2 or NR.sub.1; Y represents halogen, cyano, cyano C.sub.1-C.sub.6alkyl, carboxy, nitro, N(R.sub.2).sub.2, —(C.sub.1-C.sub.6)alkyl-N(R.sub.2).sub.2, CON(R.sub.2).sub.2, —(C.sub.1-C.sub.6)alkyl-CON(R.sub.2).sub.2, —(C.sub.1-C.sub.6)alkyl-N(R.sub.2).sub.3.sup.+I.sup.−, hydroxy C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkyl substituted by amino and carboxy, OR.sub.3, SR.sub.3, —(C.sub.1-C.sub.6)alkyl-SOR.sub.3, —(C.sub.1-C.sub.6)alkyl-OR.sub.3, —(C.sub.1-C.sub.6)alkyl-SR.sub.3, COR.sub.3, COOR.sub.3, —(C.sub.1-C.sub.6)alkyl-COR.sub.4, —(C.sub.1-C.sub.6)alkyl-COOR.sub.4, —(C.sub.1-C.sub.6)alkyl-OCOR.sub.3, Si(R.sub.3).sub.3, —(C.sub.1-C.sub.6)alkyl-O—Si(R.sub.3).sub.3, —(C.sub.1-C.sub.6)alkyl-O—N═C(R.sub.3).sub.2, C.sub.1-C.sub.6alkyl, haloC.sub.1-C.sub.6alkyl, unsubstituted or substituted C.sub.2-C.sub.6 alkenyl, unsubstituted or substituted C.sub.2-C.sub.6 alkynyl, unsubstituted or substituted C.sub.3-C.sub.6 cycloalkyl, unsubstituted or substituted C.sub.3-C.sub.6cycloalkyl unsubstituted or substituted heterocyclyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heterocyclyl C.sub.1-C.sub.6alkyl, unsubstituted or substituted aryl C.sub.1-C.sub.6alkyl, unsubstituted or substituted heteroaryl C.sub.1-C.sub.6alkyl, wherein the substituted C.sub.2-C.sub.6 alkenyl or the substituted C.sub.2-C.sub.6 alkynyl is C.sub.2-C.sub.6 alkenyl or C.sub.2-C.sub.6 alkynyl substituted by at least one group selected from the group consisting of halogen, cyano, C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.6 alkyl carbonyl, C.sub.1-C.sub.6 alkoxy carbonyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 alkylthio, C.sub.1-C.sub.6 alkyl sulfinyl, C.sub.1-C.sub.6 alkyl sulfonyl and tri(C.sub.1-C.sub.6)alkylsilyl, the substituted C.sub.3-C.sub.6 cycloalkyl or the substituted C.sub.3-C.sub.6cycloalkyl C.sub.1-C.sub.6alkyl is C.sub.3-C.sub.6 cycloalkyl or C.sub.3-C.sub.6cycloalkyl C.sub.1-C.sub.6alkyl substituted by at least one group selected from the group consisting of C.sub.1-C.sub.6 alkyl, halogen and phenyl; or, —X—Y represents ##STR00881## which is unsubstituted or substituted by 1, 2 or 3 groups selected from the group consisting of halogen, nitro, cyano, hydroxy, carboxy, amino, thiol, formyl, unsubstituted or substituted phenyl, unsubstituted or substituted benzyl, unsubstituted or substituted phenoxy, halogen-containing or halogen-free C.sub.1-C.sub.8 alkyl, halogen-containing or halogen-free C.sub.2-C.sub.8 alkenyl, halogen-containing or halogen-free C.sub.2-C.sub.8 alkynyl, halogen-containing or halogen-free C.sub.3-C.sub.8 cycloalkyl, halogen-containing or halogen-free C.sub.3-C.sub.8cycloalkyl C.sub.1-C.sub.8alkyl, halogen-containing or halogen-free C.sub.1-C.sub.8 alkoxy, halogen-containing or halogen-free C.sub.1-C.sub.8 alkylthio, halogen-containing or halogen-free C.sub.1-C.sub.8alkoxy C.sub.1-C.sub.8alkyl, halogen-containing or halogen-free C.sub.1-C.sub.8alkylthio C.sub.1-C.sub.8alkyl, halogen-containing or halogen-free C.sub.1-C.sub.8alkyl carbonyl, halogen-containing or halogen-free C.sub.1-C.sub.8alkoxy carbonyl, halogen-containing or halogen-free C.sub.1-C.sub.8alkyl sulfinyl, halogen-containing or halogen-free C.sub.1-C.sub.8alkyl sulfonyl, halogen-containing or halogen-free C.sub.1-C.sub.8alkyl amino, halogen-containing or halogen-free di(C.sub.1-C.sub.8)alkyl amino, and halogen-containing or halogen-free C.sub.1-C.sub.8alkyl acyloxy, wherein the substituted phenyl, the substituted benzyl or the substituted phenoxy is phenyl, benzyl or phenoxy substituted by 1, 2 or 3 groups selected from the group consisting of halogen, C.sub.1-C.sub.8 alkyl and C.sub.1-C.sub.8 alkoxy; Z represents hydrogen, halogen, cyano, OR.sub.4, —(C.sub.1-C.sub.6)alkyl-OR.sub.4, —O—(C.sub.1-C.sub.6)alkyl-N(R.sub.5).sub.2, —(C.sub.1-C.sub.6)alkyl-O—(C.sub.1-C.sub.6)alkyl-N(R.sub.5).sub.2, N(R.sub.5).sub.2, —(C.sub.1-C.sub.6)alkyl-(C═O).sub.m—N(R.sub.5).sub.2, —NH—(C.sub.1-C.sub.6)alkyl-N(R.sub.5).sub.2, halogen-free or halogen-containing C.sub.1-C.sub.6 alkyl, halogen-free or halogen-containing C.sub.2-C.sub.6 alkenyl, halogen-free or halogen-containing C.sub.2-C.sub.6 alkynyl, halogen-free or halogen-containing C.sub.1-C.sub.6alkoxy carbonyl, halogen-free or halogen-containing C.sub.1-C.sub.6alkoxy carbonyl C.sub.1-C.sub.6alkyl, halogen-free or halogen-containing C.sub.1-C.sub.6alkyl carbonyl, halogen-free or halogen-containing C.sub.1-C.sub.6alkyl carbonyl C.sub.1-C.sub.6alkyl, halogen-free or halogen-containing C.sub.1-C.sub.6alkyl carbonyloxy C.sub.1-C.sub.6alkyl, halogen-free or halogen-containing C.sub.1-C.sub.6 alkylthio, halogen-free or halogen-containing C.sub.1-C.sub.6alkyl sulfinyl, halogen-free or halogen-containing C.sub.1-C.sub.6alkyl sulfonyl, unsubstituted or substituted C.sub.3-C.sub.6 cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heterocyclyl C.sub.1-C.sub.6alkyl, unsubstituted or substituted aryl C.sub.1-C.sub.6alkyl, unsubstituted or substituted heteroaryl C.sub.1-C.sub.6alkyl, unsubstituted or substituted heterocyclyl carbonyl C.sub.1-C.sub.6alkyl, unsubstituted or substituted aryl carbonyl C.sub.1-C.sub.6alkyl, unsubstituted or substituted heteroaryl carbonyl C.sub.1-C.sub.6alkyl, unsubstituted or substituted heterocyclyl carbonyloxy C.sub.1-C.sub.6alkyl, unsubstituted or substituted aryl carbonyloxy C.sub.1-C.sub.6alkyl, or unsubstituted or substituted heteroaryl carbonyloxy C.sub.1-C.sub.6alkyl, wherein the substituted C.sub.3-C.sub.6 cycloalkyl is C.sub.3-C.sub.6 cycloalkyl substituted by at least one group selected from the group consisting of C.sub.1-C.sub.6 alkyl, halogen and phenyl; M represents hydrogen, OR.sub.6, SR.sub.6, COR.sub.6, COOR.sub.6, OCOR.sub.6, CON(R.sub.7).sub.2, N(R.sub.7).sub.2, NR.sub.8COOR.sub.6, NR.sub.8CON(R.sub.7).sub.2, —(C.sub.1-C.sub.6)alkyl-R, halogen-free or halogen-containing C.sub.1-C.sub.6 alkyl, halogen-free or halogen-containing C.sub.2-C.sub.6 alkenyl, halogen-free or halogen-containing C.sub.2-C.sub.6 alkynyl, halogen-free or halogen-containing C.sub.3-C.sub.6 cycloalkyl, unsubstituted or substituted aryl C.sub.1-C.sub.6alkyl, or unsubstituted or substituted heteroaryl C.sub.1-C.sub.6alkyl; R represents halogen-free or halogen-containing C.sub.2-C.sub.6 alkenyl, halogen-free or halogen-containing C.sub.2-C.sub.6 alkynyl, halogen-free or halogen-containing C.sub.3-C.sub.6 cycloalkyl, CN, OR.sub.11, OCOR.sub.11, COOR.sub.11, COR.sub.11, —O—(C═O)—O—R.sub.11, OSO.sub.2R.sub.12, SO.sub.2OR.sub.11, —S(O).sub.nR.sub.12, N(R.sub.13).sub.2, CON(R.sub.13).sub.2, SO.sub.2N(R.sub.13).sub.2, NR.sub.14COR.sub.11, NR.sub.14SO.sub.2R.sub.12, —O—(C═O)—N(R.sub.13).sub.2; R.sub.4, R.sub.6 and Ru each independently represent hydrogen, halogen-free or halogen-containing C.sub.1-C.sub.6 alkyl, halogen-free or halogen-containing C.sub.2-C.sub.6 alkenyl, halogen-free or halogen-containing C.sub.2-C.sub.6 alkynyl, halogen-free or halogen-containing C.sub.3-C.sub.6 cycloalkyl, halogen-free or halogen-containing C.sub.3-C.sub.6cycloalkyl C.sub.1-C.sub.6alkyl, halogen-free or halogen-containing C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6alkoxy C.sub.1-C.sub.6alkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted heterocyclyl C.sub.1-C.sub.6alkyl, unsubstituted or substituted heterocyclyloxy C.sub.1-C.sub.6alkyl, unsubstituted or substituted aryl, unsubstituted or substituted aryl C.sub.1-C.sub.6alkyl, unsubstituted or substituted aryloxy C.sub.1-C.sub.6alkyl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heteroaryl C.sub.1-C.sub.6alkyl, or unsubstituted or substituted heteroaryloxy C.sub.1-C.sub.6alkyl; R.sub.3 and R.sub.12 each independently represent halogen-free or halogen-containing C.sub.1-C.sub.6 alkyl, halogen-free or halogen-containing C.sub.2-C.sub.6 alkenyl, halogen-free or halogen-containing C.sub.2-C.sub.6 alkynyl, halogen-free or halogen-containing C.sub.3-C.sub.6 cycloalkyl, halogen-free or halogen-containing C.sub.3-C.sub.6cycloalkyl C.sub.1-C.sub.6alkyl, halogen-free or halogen-containing C.sub.3-C.sub.6 cycloalkenyl, halogen-free or halogen-containing C.sub.1-C.sub.6alkoxy C.sub.1-C.sub.6alkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted heterocyclyl C.sub.1-C.sub.6alkyl, unsubstituted or substituted aryl, unsubstituted or substituted aryl C.sub.1-C.sub.6alkyl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heteroaryl C.sub.1-C.sub.6alkyl; R.sub.1, R.sub.2, R.sub.5, R.sub.7, R.sub.8, R.sub.13, and R.sub.14 each independently represent hydrogen, nitro, alkoxyaminocarbonyl, trialkylsilyl, dialkylphosphonyl, N(R.sub.21).sub.2, CON(R.sub.21).sub.2, OR.sub.21, COR.sub.21, CO.sub.2R.sub.21, COSR.sub.21, OCOR.sub.21, S(O).sub.rR.sub.22, C.sub.1-C.sub.6 alkyl, halo C.sub.1-C.sub.6alkyl, C.sub.2-C.sub.6 alkenyl, halo C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6 alkynyl, halo C.sub.2-C.sub.6alkynyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.6 cycloalkenyl, halo C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.6alkoxy C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl C.sub.1-C.sub.6alkyl, aryl, aryl C.sub.1-C.sub.6alkyl, aryloxy, aryloxy C.sub.1-C.sub.6alkyl, aryl C.sub.1-C.sub.6alkyloxy, arylcarbonyl, aryl sulfonyl, heteroaryl, heteroaryl C.sub.1-C.sub.6alkyl, heteroaryloxy, heteroaryloxy C.sub.1-C.sub.6alkyl, heteroaryl C.sub.1-C.sub.6alkyloxy, heteroarylcarbonyl, heteroarylsulfonyl, heterocyclyl, heterocyclyl C.sub.1-C.sub.6alkyl, heterocyclyloxy, heterocyclyloxy C.sub.1-C.sub.6alkyl, heterocyclyl C.sub.1-C.sub.6alkyloxy, heterocyclylcarbonyl, heterocyclylsulfonyl, aryl-NR.sub.21—(C.sub.1-C.sub.6)alkyl, heteroaryl-NR.sub.21—(C.sub.1-C.sub.6)alkyl, heterocyclyl-NR.sub.21—(C.sub.1-C.sub.6)alkyl, wherein the last 35 groups as mentioned are each substituted by 0, 1, 2 or 3 groups selected from the group consisting of cyano, halogen, nitro, cyanothio, OR.sub.21, S(O).sub.rR.sub.22, N(R.sub.21).sub.2, NR.sub.21OR.sub.21, COR.sub.21, OCOR.sub.21, SCOR.sub.22, NR.sub.21COR.sub.21, NR.sub.21SO.sub.2R.sub.22, CO.sub.2R.sub.21, COSR.sub.21, CON(R.sub.21).sub.2 and C.sub.1-C.sub.6alkoxy C.sub.1-C.sub.6alkoxy carbonyl; R.sub.21 independently represents hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6 cycloalkyl, or C.sub.3-C.sub.6cycloalkyl C.sub.1-C.sub.6alkyl; R.sub.22 independently represents C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6 cycloalkyl, or C.sub.3-C.sub.6cycloalkyl C.sub.1-C.sub.6alkyl; m represents 0 or 1; n and r each independently represent 0, 1 or 2; wherein, the “heterocyclyl” refers to ##STR00882## which has 0, 1 or 2 oxo groups; the “aryl” refers to phenyl or naphthyl, and “heteroaryl” refers to ##STR00883## ##STR00884## which is unsubstituted or substituted by 0, 1, 2 or 3 groups selected from the group consisting of halogen, nitro, cyano, cyanothio, hydroxy, carboxy, thiol, formyl, unsubstituted or substituted phenyl, unsubstituted or substituted benzyl, unsubstituted or substituted phenoxy, halogen-containing or halogen-free C.sub.1-C.sub.8 alkyl, halogen-containing or halogen-free C.sub.2-C.sub.8 alkenyl, halogen-containing or halogen-free C.sub.2-C.sub.8 alkynyl, halogen-containing or halogen-free C.sub.3-C.sub.8 cycloalkyl, halogen-containing or halogen-free C.sub.3-C.sub.8 cycloalkyl C.sub.1-C.sub.8 alkyl, halogen-containing or halogen-free OR″, halogen-containing or halogen-free SR″, halogen-containing or halogen-free —(C.sub.1-C.sub.8)alkyl-OR″, halogen-containing or halogen-free —(C.sub.1-C.sub.8)alkyl-SR″, halogen-containing or halogen-free COR″, halogen-containing or halogen-free COOR″, halogen-containing or halogen-free COSR″, halogen-containing or halogen-free SOR″, halogen-containing or halogen-free SO.sub.2R″, halogen-containing or halogen-free OCOR″, halogen-containing or halogen-free SCOR″, substituted amino, substituted aminocarbonyl, —OCH.sub.2CH.sub.2—, —OCH.sub.2O—, and —OCH.sub.2CH.sub.2O—, wherein the substituted phenyl, the substituted benzyl or the substituted phenoxy is phenyl, benzyl or phenoxy substituted by 1, 2 or 3 groups selected from halogen, C.sub.1-C.sub.8 alkyl and C.sub.1-C.sub.8 alkoxy, the substituted amino or the substituted aminocarbonyl is amino or aminocarbonyl substituted by one or two groups selected from hydrogen, C.sub.1-C.sub.8 alkyl, C.sub.2-C.sub.8 alkenyl, C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.8 cycloalkyl, C.sub.3-C.sub.8cycloalkyl C.sub.1-C.sub.8alkyl, COR″, SO.sub.2R″ and OR″; R′ independently represents hydrogen, nitro, hydroxy, amino, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.8 alkyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.2-C.sub.8 alkenyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.2-C.sub.8 alkynyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.3-C.sub.8 cycloalkyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.3-C.sub.8 cycloalkenyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.3-C.sub.8cycloalkyl C.sub.1-C.sub.8alkyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.8alkoxy, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.2-C.sub.8 alkenyloxy, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.2-C.sub.8 alkynyloxy, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.3-C.sub.8 cycloalkyloxy, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.8alkoxy C.sub.1-C.sub.8alkyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.8alkoxy carbonyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.8alkylthio carbonyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.8alkylsulfonyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.8alkylsulfonyl C.sub.1-C.sub.8alkyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.8alkyl carbonyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.8alkyl carbonyl C.sub.1-C.sub.8alkyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.8alkyl acyloxy, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.8alkylamino, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.8alkylamino carbonyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.8alkoxyamino carbonyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.8alkoxy carbonyl C.sub.1-C.sub.8alkyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.8alkylamino carbonyl C.sub.1-C.sub.8alkyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing tri(C.sub.1-C.sub.8)alkylsilyl, or fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing di(C.sub.1-C.sub.8)alkylphosphonyl; R″ independently represents hydrogen, halogen-free or halogen-containing C.sub.1-C.sub.8 alkyl, halogen-free or halogen-containing C.sub.2-C.sub.8 alkenyl, halogen-free or halogen-containing C.sub.2-C.sub.8 alkynyl, halogen-free or halogen-containing C.sub.3-C.sub.8 cycloalkyl or halogen-free or halogen-containing C.sub.3-C.sub.8cycloalkyl C.sub.1-C.sub.8alkyl.

4. The N-(1,3,4-oxadiazol-2-yl)arylcarboxamide compound or a salt thereof according to claim 1, wherein X represents O, S, SO, SO.sub.2 or NR.sub.1; Y represents halogen, cyano, cyano C.sub.1-C.sub.2 alkyl, carboxy, nitro, N(R.sub.2).sub.2, —(C.sub.1-C.sub.2)alkyl-N(R.sub.2).sub.2, CON(R.sub.2).sub.2, —(C.sub.1-C.sub.2)alkyl-CON(R.sub.2).sub.2, —(C.sub.1-C.sub.2)alkyl-N(R.sub.2).sub.3.sup.+I.sup.−, hydroxy C.sub.1-C.sub.2 alkyl, C.sub.1-C.sub.2 alkyl substituted by amino and carboxy, OR.sub.3, SR.sub.3, —(C.sub.1-C.sub.2)alkyl-SOR.sub.3, —(C.sub.1-C.sub.2)alkyl-OR.sub.3, —(C.sub.1-C.sub.2)alkyl-SR.sub.3, COR.sub.3, COOR.sub.3, —(C.sub.1-C.sub.2)alkyl-COR.sub.4, —(C.sub.1-C.sub.2)alkyl-COOR.sub.4, —(C.sub.1-C.sub.2)alkyl-OCOR.sub.3, Si(R.sub.3).sub.3, —(C.sub.1-C.sub.2)alkyl-O—Si(R.sub.3).sub.3, —(C.sub.1-C.sub.2)alkyl-O—N═C(R.sub.3).sub.2, C.sub.1-C.sub.6 alkyl, halo C.sub.1-C.sub.6 alkyl; unsubstituted or substituted C.sub.2-C.sub.6 alkenyl, unsubstituted or substituted C.sub.2-C.sub.6 alkynyl, unsubstituted or substituted C.sub.3-C.sub.6 cycloalkyl, unsubstituted or substituted C.sub.3-C.sub.6 cycloalkyl C.sub.1-C.sub.2 alkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heterocyclyl C.sub.1-C.sub.2 alkyl, unsubstituted or substituted aryl C.sub.1-C.sub.2 alkyl, or unsubstituted or substituted heteroaryl C.sub.1-C.sub.2 alkyl, wherein the substituted C.sub.2-C.sub.6 alkenyl or substituted C.sub.2-C.sub.6 alkynyl is C.sub.2-C.sub.6 alkenyl or C.sub.2-C.sub.6 alkynyl substituted by at least one group selected from halogen, cyano, C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.6 alkyl carbonyl, C.sub.1-C.sub.6 alkoxy carbonyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 alkylthio, C.sub.1-C.sub.6 alkylsulfinyl, C.sub.1-C.sub.6 alkylsulfonyl, and tri(C.sub.1-C.sub.6)alkylsilyl, the substituted C.sub.3-C.sub.6 cycloalkyl or the substituted C.sub.3-C.sub.6 cycloalkyl C.sub.1-C.sub.2 alkyl is C.sub.3-C.sub.6 cycloalkyl or C.sub.3-C.sub.6 cycloalkyl C.sub.1-C.sub.2 alkyl substituted by at least one group selected from C.sub.1-C.sub.6 alkyl, halogen and phenyl; or, —X—Y represents ##STR00885## which is unsubstituted or substituted by 1, 2 or 3 groups selected from the group consisting of halogen, nitro, cyano, hydroxy, carboxy, amino, thiol, formyl, unsubstituted or substituted phenyl, unsubstituted or substituted benzyl, unsubstituted or substituted phenoxy, halogen-free or halogen-containing C.sub.1-C.sub.6 alkyl, halogen-free or halogen-containing C.sub.2-C.sub.6 alkenyl, halogen-free or halogen-containing C.sub.2-C.sub.6 alkynyl, halogen-free or halogen-containing C.sub.3-C.sub.6 cycloalkyl, halogen-free or halogen-containing C.sub.3-C.sub.6 cycloalkyl C.sub.1-C.sub.2 alkyl, halogen-free or halogen-containing C.sub.1-C.sub.6 alkoxy, halogen-free or halogen-containing C.sub.1-C.sub.6 alkylthio, halogen-free or halogen-containing C.sub.1-C.sub.6 alkoxy C.sub.1-C.sub.2 alkyl, halogen-free or halogen-containing C.sub.1-C.sub.6 alkylthio C.sub.1-C.sub.2 alkyl, halogen-free or halogen-containing C.sub.1-C.sub.6 alkyl carbonyl, halogen-free or halogen-containing C.sub.1-C.sub.6 alkoxy carbonyl, halogen-free or halogen-containing C.sub.1-C.sub.6 alkyl sulfinyl, halogen-free or halogen-containing C.sub.1-C.sub.6 alkyl sulfonyl, halogen-free or halogen-containing C.sub.1-C.sub.6 alkyl amino, halogen-free or halogen-containing di(C.sub.1-C.sub.6)alkyl amino, or halogen-free or halogen-containing C.sub.1-C.sub.6 alkyl acyloxy, wherein the substituted phenyl, the substituted benzyl or the substituted phenoxy is phenyl, benzyl or phenoxy substituted by 1, 2 or 3 groups selected from halogen, C.sub.1-C.sub.6 alkyl, and C.sub.1-C.sub.6 alkoxy; Z represents hydrogen, halogen, cyano, OR.sub.4, —(C.sub.1-C.sub.2)alkyl-OR.sub.4, —O—(C.sub.1-C.sub.2)alkyl-N(R.sub.5).sub.2, —(C.sub.1-C.sub.2)alkyl-O—(C.sub.1-C.sub.2)alkyl-N(R.sub.5).sub.2, N(R.sub.5).sub.2, —(C.sub.1-C.sub.2)alkyl-(C═O).sub.m—N(R.sub.5).sub.2, —NH—(C.sub.1-C.sub.2)alkyl-N(R.sub.5).sub.2, halogen-free or halogen-containing C.sub.1-C.sub.6 alkyl, halogen-free or halogen-containing C.sub.2-C.sub.6 alkenyl, halogen-free or halogen-containing C.sub.2-C.sub.6 alkynyl, halogen-free or halogen-containing C.sub.1-C.sub.6 alkoxy carbonyl, halogen-free or halogen-containing C.sub.1-C.sub.6 alkoxy carbonyl C.sub.1-C.sub.2 alkyl, halogen-free or halogen-containing C.sub.1-C.sub.6 alkyl carbonyl, halogen-free or halogen-containing C.sub.1-C.sub.6 alkyl carbonyl C.sub.1-C.sub.2 alkyl, halogen-free or halogen-containing C.sub.1-C.sub.6 alkyl carbonyloxy C.sub.1-C.sub.2 alkyl, halogen-free or halogen-containing C.sub.1-C.sub.6 alkylthio, halogen-free or halogen-containing C.sub.1-C.sub.6 alkyl sulfinyl, halogen-free or halogen-containing C.sub.1-C.sub.6 alkyl sulfonyl, unsubstituted or substituted C.sub.3-C.sub.6 cycloalkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heterocyclyl C.sub.1-C.sub.2 alkyl, unsubstituted or substituted aryl C.sub.1-C.sub.2 alkyl, unsubstituted or substituted heteroaryl C.sub.1-C.sub.2 alkyl, unsubstituted or substituted heterocyclylcarbonyl C.sub.1-C.sub.2 alkyl, unsubstituted or substituted aryl carbonyl C.sub.1-C.sub.2 alkyl, unsubstituted or substituted heteroaryl carbonyl C.sub.1-C.sub.2 alkyl, unsubstituted or substituted heterocyclyl carbonyloxy C.sub.1-C.sub.2 alkyl, unsubstituted or substituted aryl carbonyloxy C.sub.1-C.sub.2 alkyl, or unsubstituted or substituted heteroaryl carbonyloxy C.sub.1-C.sub.2 alkyl, wherein the substituted C.sub.3-C.sub.6 cycloalkyl is C.sub.3-C.sub.6 cycloalkyl substituted by at least one group selected from C.sub.1-C.sub.6 alkyl, halogen and phenyl; M represents hydrogen, OR.sub.6, SR.sub.6, COR.sub.6, COOR.sub.6, OCOR.sub.6, CON(R.sub.7).sub.2, N(R.sub.7).sub.2, NR.sub.8COOR.sub.6, NR.sub.8CON(R.sub.7).sub.2, —(C.sub.1-C.sub.2)alkyl-R, halogen-free or halogen-containing C.sub.1-C.sub.6 alkyl, halogen-free or halogen-containing C.sub.2-C.sub.6 alkenyl, halogen-free or halogen-containing C.sub.2-C.sub.6 alkynyl, halogen-free or halogen-containing C.sub.3-C.sub.6 cycloalkyl, unsubstituted or substituted aryl C.sub.1-C.sub.2 alkyl, or unsubstituted or substituted heteroaryl C.sub.1-C.sub.2 alkyl; R represents halogen-free or halogen-containing C.sub.2-C.sub.6 alkenyl, halogen-free or halogen-containing C.sub.2-C.sub.6 alkynyl, halogen-free or halogen-containing C.sub.3-C.sub.6 cycloalkyl, CN, OR.sub.11, OCOR.sub.11, COOR.sub.11, COR.sub.11, —O—(C═O)—O—R.sub.11, OSO.sub.2R.sub.12, SO.sub.2OR.sub.11, —S(O).sub.nR.sub.12, N(R.sub.13).sub.2, CON(R.sub.13).sub.2, SO.sub.2N(R.sub.13).sub.2, NR.sub.14COR.sub.11, NR.sub.14SO.sub.2R.sub.12, or —O—(C═O)—N(R.sub.13).sub.2; R.sub.4, R.sub.6 and R.sub.14 each independently represent hydrogen, halogen-free or halogen-containing C.sub.1-C.sub.6 alkyl, halogen-free or halogen-containing C.sub.2-C.sub.6 alkenyl, halogen-free or halogen-containing C.sub.2-C.sub.6 alkynyl, halogen-free or halogen-containing C.sub.3-C.sub.6 cycloalkyl, halogen-free or halogen-containing C.sub.3-C.sub.6 cycloalkyl C.sub.1-C.sub.2 alkyl, halogen-free or halogen-containing C.sub.3-C.sub.6 cycloalkenyl, halogen-free or halogen-containing C.sub.1-C.sub.6 alkoxy C.sub.1-C.sub.2 alkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted heterocyclyl C.sub.1-C.sub.2 alkyl, unsubstituted or substituted heterocyclyloxy C.sub.1-C.sub.2 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted aryl C.sub.1-C.sub.2 alkyl, unsubstituted or substituted aryloxy C.sub.1-C.sub.2 alkyl, unsubstituted or substituted heteroaryl, unsubstituted or substituted heteroaryl C.sub.1-C.sub.2 alkyl, or unsubstituted or substituted heteroaryloxy C.sub.1-C.sub.2 alkyl; R.sub.3 and R.sub.12 each independently represent halogen-free or halogen-containing C.sub.1-C.sub.6 alkyl, halogen-free or halogen-containing C.sub.2-C.sub.6 alkenyl, halogen-free or halogen-containing C.sub.2-C.sub.6 alkynyl, halogen-free or halogen-containing C.sub.3-C.sub.6 cycloalkyl, halogen-free or halogen-containing C.sub.3-C.sub.6 cycloalkyl C.sub.1-C.sub.2 alkyl, halogen-free or halogen-containing C.sub.3-C.sub.6 cycloalkenyl, halogen-free or halogen-containing C.sub.1-C.sub.6 alkoxy C.sub.1-C.sub.2 alkyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted heterocyclyl C.sub.1-C.sub.2 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted aryl C.sub.1-C.sub.2 alkyl, unsubstituted or substituted heteroaryl, or unsubstituted or substituted heteroaryl C.sub.1-C.sub.2 alkyl; R.sub.1, R.sub.2, R.sub.5, R.sub.7, R.sub.8, R.sub.13, and R.sub.14 each independently represent hydrogen, nitro, alkoxyaminocarbonyl, trialkylsilyl, dialkylphosphonyl, N(R.sub.21).sub.2, CON(R.sub.21).sub.2, OR.sub.21, COR.sub.21, CO.sub.2R.sub.21, COSR.sub.21, OCOR.sub.11, S(O).sub.rR.sub.22, C.sub.1-C.sub.6 alkyl, halo C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, halo C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, halo C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.6 cycloalkenyl, halo C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.6 alkoxy C.sub.1-C.sub.2 alkyl, C.sub.3-C.sub.6 cycloalkyl C.sub.1-C.sub.2 alkyl, aryl, aryl C.sub.1-C.sub.2 alkyl, aryloxy, aryloxy C.sub.1-C.sub.2 alkyl, aryl C.sub.1-C.sub.2 alkyloxy, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl C.sub.1-C.sub.2 alkyl, heteroaryloxy, heteroaryloxy C.sub.1-C.sub.2 alkyl, heteroaryl C.sub.1-C.sub.2 alkyloxy, heteroaryl carbonyl, heteroaryl sulfonyl, heterocyclyl, heterocyclyl C.sub.1-C.sub.2 alkyl, heterocyclyloxy, heterocyclyloxy C.sub.1-C.sub.2 alkyl, heterocyclyl C.sub.1-C.sub.2 alkyloxy, heterocyclyl carbonyl, heterocyclyl sulfonyl, aryl-NR.sub.21—(C.sub.1-C.sub.2)alkyl, heteroaryl-NR.sub.21—(C.sub.1-C.sub.2)alkyl, heterocyclyl-NR.sub.21—(C.sub.1-C.sub.2)alkyl, wherein the last 35 groups as mentioned are each substituted by 0, 1, 2 or 3 groups selected from the group consisting of cyano, halogen, nitro, cyanothio, OR.sub.21, S(O).sub.rR.sub.22, N(R.sub.21).sub.2, NR.sub.21OR.sub.21, COR.sub.21, OCOR.sub.21, SCOR.sub.22, NR.sub.21COR.sub.21, NR.sub.21SO.sub.2R.sub.22, CO.sub.2R.sub.21, COSR.sub.21, CON(R.sub.21).sub.2 and C.sub.1-C.sub.6 alkoxy C.sub.1-C.sub.2 alkoxy carbonyl; R.sub.21 independently represents hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6 cycloalkyl, or C.sub.3-C.sub.6 cycloalkyl C.sub.1-C.sub.2 alkyl; R.sub.22 independently represents C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6 cycloalkyl, or C.sub.3-C.sub.6cycloalkyl C.sub.1-C.sub.2 alkyl; m represents 0 or 1; n and r each independently represent 0, 1 or 2; wherein, the “heterocyclyl” refers to ##STR00886## which has 0, 1 or 2 oxo groups, the “aryl” refers to phenyl or naphthyl, and the “heteroaryl” refers to ##STR00887## ##STR00888## which is unsubstituted or substituted by 0, 1, 2 or 3 groups selected from the group consisting of halogen, nitro, cyano, cyanothio, hydroxy, carboxy, thiol, formyl, unsubstituted or substituted phenyl, unsubstituted or substituted benzyl, unsubstituted or substituted phenoxy, halogen-containing or halogen-free C.sub.1-C.sub.6 alkyl, halogen-containing or halogen-free C.sub.2-C.sub.6 alkenyl, halogen-containing or halogen-free C.sub.2-C.sub.6 alkynyl, halogen-containing or halogen-free C.sub.3-C.sub.6 cycloalkyl, halogen-containing or halogen-free C.sub.3-C.sub.6 cycloalkyl C.sub.1-C.sub.2 alkyl, halogen-containing or halogen-free OR″, halogen-containing or halogen-free SR″, halogen-containing or halogen-free —(C.sub.1-C.sub.2)alkyl-OR″, halogen-containing or halogen-free —(C.sub.1-C.sub.2 alkyl-SR″, halogen-containing or halogen-free COR″, halogen-containing or halogen-free COOR″, halogen-containing or halogen-free COSR″, halogen-containing or halogen-free SOR″, halogen-containing or halogen-free SO.sub.2R″, halogen-containing or halogen-free OCOR″, halogen-containing or halogen-free SCOR″, substituted amino, substituted aminocarbonyl, —OCH.sub.2CH.sub.2—, —OCH.sub.2O—, and —OCH.sub.2CH.sub.2O—, wherein the substituted phenyl, the substituted benzyl or the substituted phenoxy is phenyl, benzyl or phenoxy substituted by 1, 2 or 3 groups selected from halogen, C.sub.1-C.sub.6 alkyl and C.sub.1-C.sub.6 alkoxy, the substituted amino or the substituted aminocarbonyl is amino or aminocarbonyl substituted by one or two groups selected from hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.6 cycloalkyl C.sub.1-C.sub.2 alkyl, COR″, SO.sub.2R″ and OR″; R′ independently represents hydrogen, nitro, hydroxy, amino, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.6 alkyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.2-C.sub.6 alkenyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.2-C.sub.6 alkynyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.3-C.sub.6 cycloalkyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.3-C.sub.6 cycloalkenyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.3-C.sub.8 cycloalkyl C.sub.1-C.sub.2 alkyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.6 alkoxy, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.2-C.sub.6 alkenyloxy, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.2-C.sub.6 alkynyloxy, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.3-C.sub.6 cycloalkyloxy, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.6 alkoxy C.sub.1-C.sub.2 alkyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.6 alkoxy carbonyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.6 alkylthio carbonyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.6alkylsulfonyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.6 alkylsulfonyl C.sub.1-C.sub.2 alkyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.6 alkyl carbonyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.6 alkyl carbonyl C.sub.1-C.sub.2 alkyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.6 alkyl acyloxy, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.6 alkylamino, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.6 alkylamino carbonyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.6 alkoxyamino carbonyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.6 alkoxy carbonyl C.sub.1-C.sub.2 alkyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing C.sub.1-C.sub.6 alkylamino carbonyl C.sub.1-C.sub.2 alkyl, fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing tri(C.sub.1-C.sub.6)alkylsilyl, or fluorine-, chlorine-, bromine-free or fluorine-, chlorine-, bromine-containing di(C.sub.1-C.sub.6)alkylphosphonyl; R″ independently represents hydrogen, halogen-free or halogen-containing C.sub.1-C.sub.6 alkyl, halogen-free or halogen-containing C.sub.2-C.sub.6 alkenyl, halogen-free or halogen-containing C.sub.2-C.sub.6 alkynyl, halogen-free or halogen-containing C.sub.3-C.sub.6 cycloalkyl or halogen-free or halogen-containing C.sub.3-C.sub.6 cycloalkyl C.sub.1-C.sub.2 alkyl.

5. The N-(1,3,4-oxadiazol-2-yl)arylcarboxamide compound or a salt thereof according to claim 1, wherein X represents S, SO or SO.sub.2; Y represents C.sub.2-C.sub.8 alkyl, halo C.sub.1-C.sub.8 alkyl, C.sub.2-C.sub.8 alkenyl, C.sub.2-C.sub.8 alkynyl, C.sub.1-C.sub.8 alkoxy C.sub.1-C.sub.8 alkyl, hydroxy C.sub.1-C.sub.8 alkyl, cyano, cyano C.sub.1-C.sub.8 alkyl, amino C.sub.1-C.sub.8 alkyl, C.sub.1-C.sub.8 alkyl amino C.sub.1-C.sub.8 alkyl, C.sub.1-C.sub.8 alkyl carbonyl, C.sub.3-C.sub.8 cycloalkyl, C.sub.3-C.sub.8 cycloalkyl C.sub.1-C.sub.8 alkyl, di(C.sub.1-C.sub.8)alkylamino carbonyl C.sub.1-C.sub.8 alkyl, C.sub.1-C.sub.8 alkyl carbonyl C.sub.1-C.sub.8 alkyl, C.sub.1-C.sub.8 alkoxy carbonyl C.sub.1-C.sub.8 alkyl, C.sub.1-C.sub.8 alkyl carbonyloxy C.sub.1-C.sub.8 alkyl, C.sub.1-C.sub.8 alkyl sulfinyl C.sub.1-C.sub.8 alkyl, tri(C.sub.1-C.sub.8)alkylsiloxy C.sub.1-C.sub.8 alkyl, heterocyclyl, heterocyclyl C.sub.1-C.sub.8 alkyl, phenyl, heteroaryl, heteroaryl C.sub.1-C.sub.8 alkyl, —(C.sub.1-C.sub.8)alkyl-O—N═C(R′″).sub.2; wherein the heterocyclyl is ##STR00889## the heteroaryl is ##STR00890## which is unsubstituted or substituted by C.sub.1-C.sub.8 alkyl; and R′″ independently represents C.sub.1-C.sub.8 alkyl; Z represents hydrogen, or C.sub.1-C.sub.8 alkyl; M represents hydrogen, or C.sub.1-C.sub.8 alkoxy carbonyloxy C.sub.1-C.sub.8 alkyl; preferably, X represents S, SO or SO.sub.2; Y represents C.sub.2-C.sub.6 alkyl, halo C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy C.sub.1-C.sub.6 alkyl, hydroxy C.sub.1-C.sub.6 alkyl, cyano, cyano C.sub.1-C.sub.6 alkyl, amino C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 alkylamino C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 alkyl carbonyl, C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.6 cycloalkyl C.sub.1-C.sub.6 alkyl, di(C.sub.1-C.sub.6)alkylamino carbonyl C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 alkyl carbonyl C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 alkoxy carbonyl C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 alkyl carbonyloxy C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 alkyl sulfinyl C.sub.1-C.sub.6 alkyl, tri(C.sub.1-C.sub.6)alkylsiloxy C.sub.1-C.sub.6 alkyl, heterocyclyl, heterocyclyl C.sub.1-C.sub.6 alkyl, phenyl, heteroaryl, heteroaryl C.sub.1-C.sub.6 alkyl, —(C.sub.1-C.sub.6)alkyl-O—N═C(R′″).sub.2; wherein, the heterocyclyl is ##STR00891## the heteroaryl is ##STR00892## which is unsubstituted or substituted by C.sub.1-C.sub.6 alkyl; and R′″ independently represents C.sub.1-C.sub.6 alkyl; Z represents hydrogen, or C.sub.1-C.sub.6 alkyl; M represents hydrogen, or C.sub.1-C.sub.6 alkoxy carbonyloxy C.sub.1-C.sub.6 alkyl.

6. The N-(1,3,4-oxadiazol-2-yl)arylcarboxamide compound or a salt thereof according to claim 1, wherein the compound is ##STR00893## wherein Y, Z and M are as defined in any one of claims 1 to 5; preferably, the compound is any one compound selected from the compounds in Tables A1 to A151 and Tables 1 to 3.

7. A method for preparing the N-(1,3,4-oxadiazol-2-yl)arylcarboxamide compound or a salt thereof according to claim 1, wherein a) when X represents Q in the Formula I, the method comprises the following steps: reacting the compound represented by Formula V with a compound represented by VI to obtain a compound represented by Formula I-1, wherein the reaction equation thereof is as follows: ##STR00894## wherein, Q represents O, S, NR.sub.1; alternatively, b) when X represents S in Formula I, the method comprises the following steps: reacting a compound represented by Formula VII with Hal-Y to prepare a compound represented by Formula I-3, wherein the reaction equation thereof is as follows: ##STR00895## wherein Hal represents halogen, preferably fluorine, chlorine or bromine; alternatively, c) when X represents SO, or SO.sub.2 in Formula I, the method comprises the following steps: reacting a compound represented by Formula I-3 with a peroxide to prepare a compound represented by Formula I-4 and/or 1-5, wherein the reaction equation thereof is as follows: ##STR00896## ##STR00897## alternatively, d) when M is not hydrogen in Formula I, the method comprises the following steps: reacting compounds represented by Formulas I-1, I-4 or I-5 with Hal-M to prepare compounds represented by Formulas I-6, I-7, or I-8, respectively, wherein the reaction equations thereof are as follows: ##STR00898##

8. A herbicidal composition, in comprising the N-(1,3,4-oxadiazol-2-yl)arylcarboxamide compound represented by Formula I or a salt thereof according to claim 1.

9. A method for controlling a weed comprising: applying at least one of the N-(1,3,4-oxadiazol-2-yl)arylcarboxamide compound or a salt thereof according to claim 1 or a herbicidal composition comprising the N-(1,3,4-oxadiazol-2-yl)arylcarboxamide compound represented by Formula I or a salt thereof according to claim 1 in an herbicidally effective amount on a plant or in a weed area.

10. (canceled)

11. The method according to claim 7, wherein: in a), the reaction is carried out in the presence of a halogenating agent, a catalyst and a solvent, the halogenating agent is SOCl.sub.2, the catalyst is 4-dimethylaminopyridine, and the solvent is pyridine, the reaction is conducted at a temperature of 0 to 50° C.; in b), the reaction is carried out in the presence of a base and a solvent, the base is one base or two bases in combination selected from the group consisting of potassium carbonate and sodium carbonate, the solvent is one solvent or more solvents in combination selected from the group consisting of DCM, DCE, ACN, THF, and DMF, the reaction is conducted at a temperature of 0 to 25° C.; in c), the peroxide is ##STR00899## the reaction is carried out in the presence of a solvent; the solvent is one solvent or two solvents in combination selected from the group consisting of DCM and DCE, and the reaction is conducted at a temperature of 0 to 50° C.; in d), the reaction is carried out in the presence of a base and a solvent, the base is one base or two bases in combination selected from the group consisting of potassium carbonate and sodium carbonate, the solvent is one solvent or more solvents in combination selected from the group consisting of DCM, DCE, ACN, THF, and DMF, the reaction is conducted at a temperature of 0 to 100° C.; or the reaction is carried out in the presence of a catalyst and a solvent, the catalyst is 4-dimethylaminopyridine, the solvent is pyridine, and the reaction is conducted at a temperature of 0 to 80° C.

12. The herbicidal composition according to claim 8, wherein the herbicidal composition further comprises one or more additional herbicides and/or safeners.

13. The herbicidal composition according to claim 12, wherein the herbicidal composition further comprises an agrochemically acceptable formulation auxiliary.

14. The herbicidal composition according to claim 12, wherein the additional herbicide is selected from the following compounds or salt or ester derivatives thereof: a) ALS inhibitors: Pyrazosulfuron-ethyl, Penoxsulam, Bispyribac-sodium, Pyriminobac-methyl, Metazosulfuron, Propyrisulfuron, Triafamone; b) ACCase inhibitors: Cyhalofop-butyl, Metamifop; c) hormones inhibitors: Quinclorac, MCPA, 2,4-D, 2,4-D butyric acid, Fluroxypyr, Florpyrauxifen-benzyl, MCPA butyric acid, Dicamba, Quintrione, Clopyralid, Trichlopyr; d) cell division inhibitors: Pendimethalin, Butralin; e) lipid synthesis (non-ACC) inhibitors: Benthiocarb, Molinate; f) HPPD inhibitors: Sanzuohuangcaotong (), Shuangzuocaotong () Huanbifucaotong (), Mesotrione, Benzobicylon, Tefuryltrione; g) PDS inhibitors: Diflufenican, Fluorochloridone, Beflubutamid; h) PPO inhibitors: Carfentrazone-ethyl, Pyraclonil, Oxadiazon, Oxadiargyl, Oxyfluorfen, Pentoxazone; i) Long-chain fatty acid synthesis inhibitors: Butachlor, Pretilachlor, Mefenacet, Anilofos, Fentrazamide, Metolachlor, Piperophos, Pyroxasulfone; j) PSII inhibitors: Simetryn, Prometryn, Amicarbazone, Isoproturon, Bromacil, Pyridate, Chlortoluron, Bentazone, Propanil, Metribuzin, Atrazine, Bromoxynil, Bromoxynil octanoate, Terbuthylazine; k) DOXP inhibitors: Clomazone; l) Others: Oxaziclomefone, Cinmethylin, Indanofan.

15. The herbicidal composition according to claim 8, wherein the herbicidal composition further comprises an agrochemically acceptable formulation auxiliary.

16. The method according to claim 9, wherein the plant is rice, and the weed is a gramineous weed, a broad-leaved weed, or a cyperaceae weed.

17. The method according to claim 16, wherein the rice is indica rice or japonica rice.

18. The method according to claim 16, wherein the weed is Echinochloa phyllopogon, Leptochloa chinensis, Echinochloa crusgali, Digitaria sanguinalis, Setaria viridis, Monochoria vaginalis, Sagittaria trifolia, Abutilon theophrasti, Amaranthus retroflexus, Stellaria media, Cyperus difformis, or Scirpus juncoides.

Description

SPECIFIC MODE FOR CARRYING OUT THE INVENTION

[0160] 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.

[0161] In view of economics, variety and biological activity of a compound, we preferably synthesized several compounds, part of which are listed in the following Table A1-A152. The structure and information of a certain compound are shown in Table A1 and Table 1. The compounds in Table A1-A152 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 A1 Structures and 1H NMR data of compounds I [00031] Compound No. X Y Z M .sup.1HNMR 1-1 S Me Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.35 (s, 1H), 7.84 (dd, J = 8.0, 7.0 Hz, 1H), 7.75 (d, J = 8.0 Hz, 1H), 2.50 (s, 3H), 2.48 (s, 3H). 1-2 SO Me Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.37 (s, 1H), 8.04 (dd, J = 8.0, 7.0 Hz, 1H), 7.78 (d, J = 8.0 Hz, 1H), 3.35 (s, 3H), 2.50 (s, 3H). 1-3 SO.sub.2 Me Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.39 (s, 1H), 8.24 (dd, J = 8.0, 7.0 Hz, 1H), 7.98 (d, J = 8.0 Hz, 1H), 3.45 (s, 3H), 2.50 (s, 3H). 1-4 S Et Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.39 (s, 1H), 7.88 (dd, J = 8.0, 7.0 Hz, 1H), 7.78 (d, J = 8.0 Hz, 1H), 2.98 (q, J = 7.5 Hz, 2H) 2.51 (s, 3H), 1.15 (t, J = 7.5 Hz, 3H). 1-5 SO Et Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.37 (s, 1H), 8.04 (dd, J = 8.0, 7.0 Hz, 1H), 7.78 (d, J = 8.0 Hz, 1H), 3.47 (q, J = 7.5 Hz, 2H), 2.50 (s, 3H), 1.12 (t, J = 7.5 Hz, 3H). 1-6 SO2 Et Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.41 (s, 1H), 8.22 (dd, J = 8.0, 7.0 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 3.54 (q, J = 7.5 Hz, 2H), 2.49 (s, 3H), 1.20 (t, J = 7.5 Hz, 3H). 1-7 S [00032] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.38 (s, 1H), 7.86 (dd, J = 8.0, 7.0 Hz, 1H), 7.77 (d, J = 8.0 Hz, 1H), 2.95 (t, J = 7.5 Hz, 2H), 2.50 (s, 3H), 1.25-1.20 (m, 2H), 0.90 (t, J = 7.5 Hz, 3H). 1-8 SO [00033] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.57 (s, 1H), 8.07 (dd, J = 8.0, 7.0 Hz, 1H), 7.82 (d, J = 8.0 Hz, 1H), 3.57-3.47 (m, 2H), 2.48 (s, 3H), 1.70- 1.52 (m, 2H), 1.08-0.93 (m, 3H). 1-9 SO.sub.2 [00034] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.59 (s, 1H), 8.27 (dd, J = 8.0, 7.0 Hz, 1H), 3.75 (t, J = 7.5 Hz, 2H), 2.48 (s, 3H), 1.80-1.62 (m, 2H), 1.05 (t, J = 7.5 Hz, 3H). 1-10 S [00035] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.42 (s, 1H), 7.89 (dd, J = 8.0, 7.0 Hz, 1H), 7.80 (d, J = 8.0 Hz, 1H), 3.52 (hept., J = 7.5 Hz, 1H) 2.51 (s, 3H), 1.22 (d, J = 7.5 Hz, 6H). 1-11 SO [00036] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.55 (s, 1H), 8.17 7.0 Hz, 1H), 7.88 (d, J = 8.0 Hz, 1H), 3.80-3.73 (m, 1H), 2.50 (s, 3H), 1.47 (d, J = 7.0, 3H), 0.98 (d, J = 7.0 Hz, 3H). 1-12 SO2 [00037] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.75 (s, 1H), 8.27 (dd, J = 8.0, 7.0 Hz, 1H), 8.08 (d, J = 8.0 Hz, 1H), 3.89 (hept., J = 7.5 Hz, 1H), 2.50 (s, 3H), 1.27 (d, J = 7.0, 6H). 1-13 S [00038] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.25 (s, 1H), 7.86 (dd, J = 8.0, 7.0 Hz, 1H), 7.77 (d, J = 8.0 Hz, 1H), 2.99 7.5 Hz, 2H), 2.50 (s, 3H), 1.48-1.42 (m, 2H), 1.39- 1.33 (m, 2H), 0.83 (t, J = 7.5 Hz, 3H). 1-14 SO [00039] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.27 (s, 1H), 8.06 (dd, J = 8.0, 7.0 Hz, 1H), 7.88 (d, J = 8.0 Hz, 1H), 3.57 (t, J = 7.5 Hz, 2H), 2.48 (s, 3H), 1.72-1.46 (m, 4H), 0.93 (t, J = 7.5 Hz, 3H). 1-15 SO.sub.2 [00040] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.47 (s, 1H), 8.26 (dd, J = 8.0, 7.0 Hz, 1H), 8.08 (d, J = 8.0 Hz, 1H), 3.77 (t, J = 7.5 Hz, 2H), 2.48 (s, 3H), 1.82-1.56 (m, 4H), 1.02 (t, J = 7.5 Hz, 3H). 1-16 S [00041] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.40 (s, 1H), 7.93 (dd, J = 8.0, 7.0 Hz, 1H), 7.63 (d, J = 8.0 Hz, 1H), 3.68-3.60 (m, 1H), 2.50 (s, 3H), 1.75- 1.66 (m, 2H), 1.18 (d, J = 7.0 Hz, 3H), 1.07 (t, J = 7.5 Hz, 3H). 1-17 SO [00042] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.41 (s, 1H), 8.12 (dd, J = 8.0, 7.0 Hz, 1H), 7.83 (d, J = 8.0 Hz, 1H), 3.88-3.80 (m, 1H), 2.50 (s, 3H), 1.85- 1.73 (m, 2H), 1.23 (d, J = 7.0 Hz, 3H), 1.10 (t, J = 7.5 Hz, 3H). 1-18 SO.sub.2 [00043] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.43 (s, 1H), 8.32 (dd, J = 8.0, 7.0 Hz, 1H), 8.04 (d, J = 8.0 Hz, 1H), 4.08-4.00 (m, 1H), 2.50 (s, 3H), 1.95- 1.85 (m, 2H), 1.30 (d, J = 7.0 Hz, 3H), 1.14 (t, J = 7.5 Hz, 3H). 1-19 S [00044] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.38 (s, 1H), 7.85 (dd, J = 8.0, 7.0 Hz, 1H), 7.59 (d, J = 8.0 Hz, 1H), 3.46 (d, J = 7.0 Hz, 2H), 2.50 (s, 3H), 1.82-1.77 (m, 1H), 1.15 (d, J = 7.5 Hz, 6H). 1-20 SO [00045] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.41 (s, 1H), 8.05 (dd, J = 8.0, 7.0 Hz, 1H), 7.79 (d, J = 8.0 Hz, 1H), 3.55 (d, J = 7.0 Hz, 2H), 2.50 (s, 3H), 1.92-1.86 (m, 1H), 1.20 (d, J = 7.5 Hz, 6H). 1-21 SO.sub.2 [00046] Me H .sup.1H NMR (500 MHz, DMSO-d6) 1H), 8.26 (dd, J = 8.0, 7.0 Hz, 1H), 7.99 (d, J = 8.0 Hz, 1H), 3.75 (d, J = 7.0 Hz, 2H), 2.50 (s, 3H), 1.99-1.92 (m, 1H), 1.27 (d, J = 7.5 Hz, 6H). 1-22 S [00047] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.36 (s, 1H), 7.94 (dd, J = 8.0, 7.0 Hz, 1H), 7.68 (d J = 8.0 Hz, 1H), 3.25 (t, J = 7.5 Hz, 2H), 2.50 (s, 3H), 1.72-1.48 (m, 6H), 1.10 (t, J = 7.5 Hz, 3H). 1-23 SO [00048] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.37 (s, 1H), 8.05 (dd, J = 8.0, 7.0 Hz, 1H), 7.75 (d J = 8.0 Hz, 1H), 3.45 (t, J = 7.5 Hz, 2H), 2.50 (s, 3H), 1.82-1.56 (m, 6H), 1.12 (t, J = 7.5 Hz, 3H). 1-24 SO.sub.2 [00049] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.37 (s, 1H), 8.25 (dd, J = 8.0, 7.0 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 3.66 (t, J = 7.5 Hz, 2H), 2.50 (s, 3H), 1.99-1.56 (m, 6H), 1.15 (t, J = 7.5 Hz, 3H). 1-25 S [00050] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.37 (s, 1H), 7.96 (dd, J = 8.0, 7.0 Hz, 1H), 7.65 (d, J = 8.0 Hz, 1H), 3.27 (t, J = 7.5 Hz, 2H), 2.50 (s, 3H), 1.75-1.66 (m, 3H), 1.18 (d, J = 7.5 Hz, 6H). 1-26 SO [00051] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.37 (s, 1H), 8.04 (dd, J = 8.0, 7.0 Hz, 1H), 3.49 (t, J = 7.5 Hz, 2H), 2.50 (s, 3H), 1.82-1.76 (m, 3H), 1.22 (d, J = 7.5 Hz, 6H). 1-27 SO.sub.2 [00052] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.39 (s, 1H), 8.25 (dd, J = 8.0, 7.0 Hz, 1H), 3.68 (t, J = 7.5 Hz, 2H), 2.50 (s, 3H), 1.92-1.86 (m, 3H), 1.26 (d, J = 7.5 Hz, 6H). 1-28 S [00053] Me H .sup.1H NMR DMSO-d6) 12.40 (s, 1H), 7.88 (dd, J = 8.0, 7.0 Hz, 1H), 7.61 (d, J = 8.0 Hz, 1H), 3.32 (d, J = 7.0 Hz, 2H), 2.50 (s, 3H), 1.82-1.63 (m, 3H), 1.23 (d, J = 7.5 Hz, 3H), 1.08 (t, J = 7.5 Hz, 3H). 1-29 SO [00054] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.41 (s, 1H), 8.05 (dd, J = 8.0, 7.0 Hz, 1H), 7.79 (d, J = 8.0 Hz, 1H), 3.55 (d, J = 7.0 Hz, 2H), 2.50 (s, 3H), 1.92-1.66 (m, 3H), 1.29 (d, J = 7.5 Hz, 3H), 1.10 (t, J = 7.5 Hz, 3H). 1-30 SO.sub.2 [00055] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.42 (s, 1H), 8.25 (dd, J = 8.0, 7.0 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 3.76 (d, J = 7.0 Hz, 2H), 2.50 (s, 3H), 1.99-1.69 (m, 3H), 1.36 (d, J = 7.5 Hz, 3H), 1.17 (t, J = 7.5 Hz, 3H). 1-31 S [00056] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.37 (s, 1H), 7.98 (dd, J = 8.0, 7.0 Hz, 1H), 7.60 (d, J = 8.0 Hz, 1H), 3.27 (t, J = 7.5 Hz, 2H), 2.51 (s, 3H), 1.76-1.48 (m, 8H), 1.05 (t, J = 7.5 Hz, 3H). 1-32 SO [00057] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.38 (s, 1H), 8.05 (dd, J = 8.0, 7.0 Hz, 1H), 7.81 (d, J = 8.0 Hz, 1H), 3.47 (t, J = 7.5 Hz, 2H), 2.51 (s, 3H), 1.85-1.55 (m, 8H), 1.10 (t, J = 7.5 Hz, 3H). 1-33 SO.sub.2 [00058] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.39 (s, 1H), 8.25 (dd, J = 8.0, 7.0 Hz, 1H), 7.98 (d J = 8.0 Hz, 1H), 3.69 (t, J = 7.5 Hz, 2H), 2.51 (s, 3H), 1.95-1.57 (m, 8H), 1.19 (t, J = 7.5 Hz, 3H). 1-34 S [00059] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.37 (s, 1H), 7.87 (dd, J = 8.0, 7.0 Hz, 1H), 7.60 (d, J = 8.0 Hz, 1H), 3.28 (t, J = 7.5 Hz, 2H), 2.50 (s, 3H), 1.76 -1.51 (m, 10H), 1.08 (t, J = 7.5 Hz, 3H). 1-35 SO [00060] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.38 (s, 1H), 8.07 (dd, J = 8.0, 7.0 Hz, 1H), 3.48 (t, J = 7.5 Hz, 2H), 2.50 (s, 3H), 1.85-1.53 (m, 10H), 1.10 (t, J = 7.5 Hz, 3H). 1-36 SO.sub.2 [00061] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.39 (s, 1H), 8.27 (dd, J = 8.0, 7.0 Hz, 1H), 3.68 (t, J = 7.5 Hz, 2H), 2.50 (s, 3H), 1.94-1.55 (m, 10H), 1.12 (t, J = 7.5 Hz, 3H). 1-37 S [00062] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.12 (s, 1H), 8.10 (dd, J = 8.0, 7.0 Hz, 1H), 7.99 (d, J = 8.0 Hz, 1H), 6.46-6.35 (m, 1H), 5.43- 5.32 (m, 2H), 2.50 (s, 3H). 1-38 SO [00063] Me H 1-39 SO.sub.2 [00064] Me H 1-40 S [00065] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.40 (s, 1H), 7.95 (dd, J = 8.0, 7.0 Hz, 1H), 7.80 (d, J = 8.0 Hz, 1H), 6.01 ?+05.92 (m, 1H), 5.21 ?+05.12 (m, 2H), 3.82 ?+0 3.76 (m, 2H), 2.50 (s, 3H) 1-41 S [00066] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.23 (s, 1H), 8.10 (dd, J = 8.0, 7.0 Hz, 1H), 7.99 (d, J = 8.0 Hz, 1H), 3.12 (s, 1H), 2.50 (s, 3H). 1-42 S [00067] Me H 1-43 S [00068] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.40 (s, 1H), 8.02 (dd, J = 8.0, 7.0 Hz, 1H), 7.86 (d, J = 8.0 Hz, 1H), 3.35 (s, 2H), 2.95 (s, 1H), 2.49 (s, 3H) 1-44 S [00069] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.33 (s, 1H), 8.13 7.0 Hz, 1H), 8.00 (d, J = 8.0 Hz, 1H), 6.65 (t, J = 73..5 Hz, 1H), 2.50 (s, 3H). 1-45 SO [00070] Me H 1-46 SO.sub.2 [00071] Me H 1-47 S [00072] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.48 (s, 1H), 8.18 (dd, J = 8.0, 7.0 Hz, 1H), 8.07 (d, J = 8.0 Hz, 1H), 2.51 (s, 3H) 1-48 S [00073] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.40 (s, 1H), 7.95 (dd, J = 8.0, 7.0 Hz, 1H), 8.0 Hz, 1H), 4.53-4.40 (m, 2H), 3.11- 3.00 (m, 2H), 2.50 (s, 3H) 1-49 S [00074] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.41 (s, 1H), 7.97 (dd, J = 8.0, 7.0 Hz, 1H) 8.0 Hz, 1H), 5.59-5.41 (m, 1H), 3.21- 3.10 (m, 2H), 2.50 (s, 3H) 1-50 S [00075] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.43 (s, 1H), 7.98 (dd, J = 8.0, 7.0 Hz, 1H), 7.86 (d, J = 8.0 Hz, 1H), 3.45-3, 38 (m, 2H), 2.51 (s, 3H) 1-51 S [00076] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.40 (s, 1H), 7.95 (dd, J = 8.0, 7.0 Hz, 1H), 7.83 (d, J = 8.0 Hz, 1H), 2.93-2.80 (m, 2H), 2.21- 2.10 (m, 2H), 2.50 (s, 3H) 1-52 SO [00077] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.42 (s, 1H), 8.15 (dd, J = 8.0, 7.0 Hz, 1H), 8.03 (d, J = 8.0 Hz, 1H), 3.13-2.96 (m, 2H), 2.28- 2.13 (m, 2H), 2.50 (s, 3H) 1-53 SO.sub.2 [00078] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.43 (s, 1H), 8.34 (dd, J = 8.0, 7.0 Hz, 1H), 8.21 (d, J = 8.0 Hz, 1H), 3.13-3.00 (m, 2H), 2.31- 2.70 (m, 2H), 2.50 (s, 3H) 1-54 S [00079] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.41 (s, 1H), 7.93 (dd, J = 8.0, 7.0 Hz, 1H), 7.81 (d, J = 8.0 Hz, 1H), 3.73 (t, J = 8.0 Hz, 2H), 3.11 (t, J = 8.0 Hz, 2H), 2.50 (s, 3H) 1-55 S [00080] Me H 1-56 S [00081] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.41 (s, 1H), 7.93 (dd, J = 8.0, 7.0 Hz, 1H), 7.81 (d, J = 8.0 Hz, 1H), 3.78 (t, J = 8.0 Hz, 2H), 3.31 (t, J = 8.0 Hz, 2H), 3.21 (s, 3H), 2.50 (s, 3H) 1-57 SO [00082] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.42 (s, 1H), 8.13 (dd, J = 8.0, 7.0 Hz, 1H), 8.01 (d, J = 8.0 Hz, 1H), 3.98 (t, J = 8.0 Hz, 2H), 3.39 (t, J = 8.0 Hz, 2H), 3.31 (s, 3H), 2.50 (s, 3H) 1-58 SO.sub.2 [00083] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.44 (s, 1H), 8.33 (dd, J = 8.0, 7.0 Hz, 1H), 8.23 (d, J = 8.0 Hz, 1H), 4.17 (t, J = 8.0 Hz, 2H), 3.48 (t, J = 8.0 Hz, 2H), 3.33 (s, 3H), 2.50 (s, 3H) 1-59 S [00084] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.41 (s, 1H), 7.93 (dd, J = 8.0, 7.0 Hz, 1H), 7.81 (d, J = 8.0 Hz, 1H), 3.78 (t, J = 8.0 Hz, 2H), 3.31 (t, J = 8.0 Hz, 2H), 2.50 (s, 3H) 1-60 S [00085] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.40 (s, 1H), 7.92 (dd, J = 8.0, 7.80 (d, J = 3.38 (t, J = 8.0 Hz, 2H), 2.61 (t, J = 8.0 Hz, 2H), 2.50 (s, 3H), 2, 21 (s, 6H) 1-61 SO [00086] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.42 (s, 1H), 8.12 (dd, J = 8.0, 7.0 Hz, 1H), 8.00 (d, J = 8.0 Hz, 1H), 3.58 (t, J = 8.0 Hz, 2H), 2.72 (t, J = 8.0 Hz, 2H), 2.50 (s, 3H), 2.23 (s, 6H) 1-62 SO.sub.2 [00087] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.44 (s, 1H), 8.32 (dd, J = 8.0, 7.0 Hz, 1H), 8.20 (d, J = 8.0 Hz, 1H), 3.77 (t, J = 8.0 Hz, 2H), 2.83 (t, J = 8.0 Hz, 2H), 2.50 (s, 3H), 2, 24 (s, 6H) 1-63 S [00088] Me H .sup.1H NMR (500 MHz, DMSO-d6) 7.91 (dd, J = 8.0, 7.0 Hz, 1H), 7.80 (d, J = 8.0 Hz, 1H), 3.80- 3.69 (m, 1H), 3.11-3.03 (m, 2H), 2.50 (s, 3H) 1-64 S [00089] Me H 1-65 SO.sub.2 [00090] Me H 1-66 SO [00091] Me H 1-67 S [00092] Me H 1-68 S [00093] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.49 (s, 1H), 8.19 (dd, J = 8.0, 7.0 Hz, 1H), 8.09 (d, J = 8.0 Hz, 1H), 2.51 (s, 3H) 1-69 S [00094] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.43 (s, 1H), 8.05 (dd, J = 8.0, 7.0 Hz, 1H), 7.89 (d, J = 8.0 Hz, 1H), 4.22 (s, 2H), 2.50 (s, 3H) 1-70 S [00095] H .sup.1H NMR (500 MHz, DMSO-d6) 12.43 (s, 1H), 8.12 (dd, J = 8.0, 7.0 Hz, 1H), 8.06 (d, J = 8.0 Hz, 1H), 2.51 (s, 3H), 2.34 (s, 3H) 1-71 S [00096] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.43 (s, 1H), 7.97 (dd, J = 8.0, 7.0 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 4.17 (s, 2H), 4.10 (q, J = 8.0 Hz, 2H), 2.51 (s, 3H), 1.29 (t, J = 8.0 Hz, 3H) 1-72 SO [00097] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.45 (s, 1H), 8.17 (dd, J = 8.0, 7.0 Hz, 1H), 8.05 (d, J = 8.0 Hz, 1H), 4.37 (s, 2H), 4.13 (q, J = 8.0 Hz, 2H), 2.51 (s, 3H), 1.30 (t, J = 8.0 Hz, 3H) 1-73 SO.sub.2 [00098] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.46 (s, 1H), 8.37 (dd, J = 8.0, 7.0 Hz, 1H), 8.25 (d, J = 8.0 Hz, 1H), 4.57 (s, 2H), 4.19 (q, J = 8.0 Hz, 2H), 2.51 (s, 3H), 1.33 (t, J = 8.0 Hz, 3H) 1-74 S [00099] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.40 (s, 1H), 7.90 (dd, J = 8.0, 7.0 Hz, 1H), 7.80 (d, J = 8.0 Hz, 1H), 3.69 (s, 3H), 3.57 (t, J = 8.5 Hz, 2H), 2, 67 (t, J = 8.5 Hz, 2H), 2.50 (s, 3H) H 1-75 S [00100] Me H 1-76 S [00101] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.41 (s, 1H), 7.90 (dd, J = 8.0, 8.0 Hz, 1H), 2.50 (s, 3H), 1.67-1.58 (m, 1H), 1.17- 0.92 (m, 4H) 1-77 SO [00102] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.51 (s, 1H), 8.10 (dd, J = 8.0, 8.0 Hz, 1H), 2.50 (s, 3H), 1.78-1.69 (m, 1H), 1.20- 0.95 (m, 4H) 1-78 SO.sub.2 [00103] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.55 (s, 1H), 8.29 (dd, J = 8.0, 7.0 Hz, 1H), 8.17 (d, J = 8.0 Hz, 1H), 2.50 (s, 3H), 1.98-1.89 (m, 1H), 1.25- 0.99 (m, 4H) 1-79 S [00104] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.37 (s, 1H), 7.86- 7.83 (m, 1H), 7.76 (d, J = 8.0 Hz, 1H), 2.46 (s, 3H), 1.79 (d, J = 11.5 Hz, 2H), 1.70- 1.63 (m, 2H), 1.56- 1.49 (m, 1H), 1.35- 1.15(m, 6H) 1-80 SO.sub.2 [00105] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.43 (s, 1H), 8.19 (dd, J = 8.0, 7.0 Hz, 1H), 8.07 (d, J = 8.0 Hz, 1H), 3.92-3.83 (m, 1H), 3.11- 2.99 (m, 2H), 2.50 (s, 3H). 1-81 SO.sub.2 [00106] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.47 (s, 1H), 8.22 (dd, J = 8.0, 7.0 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 3.55-3.48 (m, 2H), 2.49 (s, 3H), 2.41- 2.32 (m, 3H) 1-82 SO [00107] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.41 (s, 1H), 8.13 (dd, J = 8.0, 7.0 Hz, 1H), 8.01 (d, J = 8.0 Hz, 1H), 5.11-.5.01 (m, 4H), 4.25- 4.16 (m, 1H), 2.50 (s, 3H) 1-83 S [00108] Me H 1-84 S [00109] Me H 1-85 SO.sub.2 [00110] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.47 (s, 1H), 8.22 (dd, J = 8.0, 7.0 Hz 1H), 7.96 (d, J = 8.0 Hz, 1H), 3.15-3.01 (m, 4H), 2.49 (s, 3H), 1.49- 1.42 (m, 6H) 1-86 S [00111] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.40 (s, 1H), 7.85 (t, d, J = 7.5 Hz, 1H), 7.69 (d, J = 8.0 Hz, 1H), 7.25- 7.16 (m, 5H), 4.18 (s, 2H), 2.47 (s, 3H). 1-87 S [00112] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.40 (s, 1H), 7.90 7.0 Hz, 1H), 7.80 (d, J = 8.0 Hz, 1H), 7.27-7.17 (m, 5H), 3.17 (t, J = 8.5 Hz, 2H), 3.07 (t, J = 8.5 Hz, 2H), 2.50 (s, 3H) 1-88 S [00113] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.33 (s, 1H), 8.03 (dd, J = 8.0, 7.0 Hz, 1H), 7.93 (d, J = 8.0 Hz, 1H), 7.47-7.32 (m, 5H), 2.51 (s, 3H). 1-89 S [00114] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.39 (s, 1H), 8.82 (d, J = 5.5 Hz, 2H), 8.09 (dd, J = 8.0, 7.0 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.45 (d, J = 5.5 Hz, 2H), 2.51 (s, 3H). 1-90 S [00115] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.31 (s, 1H), 8.12 (s, 1H), 8.09 (dd, J = 8.0, 7.0 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.85 (s, 1H), 3.81 (s, 3H), 2.51 (s, 3H). 1-91 S [00116] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.47 (s, 1H), 8.22 (dd, J = 8.0, 7.0 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 2.65 (s, 3H), 2.49 (s, 3H) 1-92 S [00117] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.41 (s, 1H), 8.13 (dd, J = 8.0, 7.0 Hz, 1H), 7.99 (d, J = 8.0 Hz, 1H), 3.91 (s, 3H), 2.51 (s, 3H). 1-93 S [00118] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.41 (s, 1H), 7.95 (dd, J = 8.0, 7.0 Hz, 1H), 7.83 (d, J = 8.0 Hz, 1H), 7.50 (d, J = 2.0 Hz, 1H), 6.31 (dd, J = 2.5, 2.0 Hz, 1H), 6.15 (d, J = 2.5 Hz, 1H), 3.97 (s, 2H), 2.50 (s, 3H) 1-94 S Et Me Me 1-95 S Et Me Et 1-96 S Et Me [00119] 1-97 S Et Me [00120] 1-98 S Et Me [00121] 1-99 S Et Me [00122] 1-100 S Et Me [00123] 1-101 S Et Me [00124] 1-102 S Et Me [00125] 1-103 S Et Me [00126] 1-104 S Et Me [00127] 1-105 S Et Me [00128] 1-106 S Et Me [00129] 1-107 S Et Me [00130] 1-108 S Et Me [00131] 1-109 S Et Me [00132] .sup.1H NMR (500 MHz, DMSO-d6) 7.98 (dd, J = 8.0, 7.0 Hz, 1H), 7.88 (d, J = 8.0 Hz, 1H), 6, 32 (q, J = 7.5 Hz, 1H), 4.11 (q, J = 8.5, 2H), 2.98 (q, J = 7.5 Hz, 2H) 2.51 (s, 3H), 1.56 (d, J = 7.5 Hz, 3H), 1.32 (t, J = 8.5 Hz, 3H), 1.15 (t, J = 7.5 Hz, 3H). 1-110 S Et Me [00133] 1-111 S Et Me [00134] 1-112 S Et Me [00135] .sup.1H NMR (500 MHz, DMSO-d6) 7.99 (dd, J = 8.0, 7.0 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.31- 7.20 (m, 5H), 4.97 (s, 2H), 2.99 (q, J = 7.5 Hz, 2H) 2.51 (s, 3H), 1.15 (t, J = 7.5 Hz, 3H). 1-113 S Et Me [00136] 1-114 S Et Me [00137] 1-115 S Et Me [00138] 1-116 S Et Me [00139] 1-117 S Et Me [00140] 1-118 S Et Me [00141] .sup.1H NMR (500 MHz, DMSO-d6) 8.07 (dd, J = 8.0, 7.0 Hz, 1H), 7.89 (d, J = 8.0 Hz, 1H), 3.61- 3.52 (m, 4H), 3.31-3.23 (m, 4H), 2.98 (q, J = 7.5 Hz, 2H) 2.53 (s, 3H), 1.15 (t, J = 7.5 Hz, 3H). 1-119 S Et Me [00142] .sup.1H NMR (500 MHz, DMSO-d6) 8.08 (dd, J = 8.0, 7.0 Hz, 1H), 7.89 (d, J = 8.0 Hz, 1H), 2.98 (q, J = 7.5 Hz, 2H) 2.51 (s, 3H), 2.27 (s, 3H), 1.15 (t, J = 7.5 Hz, 3H). 1-120 S Et Me [00143] 1-121 S Et Me [00144] 1-122 S Et Me [00145] 1-123 S Et Me [00146] 1-124 S Et Me [00147] 1-125 S Et Me [00148] 1-126 O Me Me .sup.1H NMR (500 MHz, DMSO-d6) 7.60-7.48 (m, 2H), 3.96 (s, 3H), 2.50 (s, 3H). 1-127 O Et Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.12 (s, 1H), 7.61- 7.50 (m, 2H), 4.18 (q, J = 7.5 Hz, 2H), 2.50 (s, 3H), 1.20 (t, J = 7.5 Hz, 3H). 1-128 O [00149] Me H 1-129 O [00150] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.41 (s, 1H), 7.99- 7.88 (m, 2H), 4.51 (q, J = 13.5 Hz, 2H), 2.50 (s, 3H) 1-130 O [00151] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.12 (s, 1H), 7.61- 7.50 (m, 2H), 4.53-4.20 (m, 4H), 2.50 (s, 3H) 1-131 NH Me Me H 1-132 NMe Me Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.12 (s, 1H), 7.61- 7.50 (m, 2H), 3.08 (s, 6H), 2.50 (s, 3H). 1-133 NMe Et Me H 1-134 -X-Y represents   [00152] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.32 (s, 1H), 8.10 (dd, J = 8.0, 7.0 Hz, 1H), 7.99 (d, J = 8.0 Hz, 1H), 3.73-3.66 (m, 2H), 2.50 (s, 3H), 2.45- 2.38 (m, 2H), 1.98-1.89 (m, 2H). 1-135 -X-Y represents   [00153] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.43 (s, 1H), 7.99- 7.82 (m, 2H), 7.52-7.40 (m, 3H), 2.50 (s, 3H) 1-136 S [00154] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.35 (s, 1H), 7.94 (dd, J = 8.0, 7.0 Hz, 1H), 7.59 (d, J = 8.0 Hz, 1H), 2.50 (s, 3H), 1.28 (s, 9H) 1-137 SO [00155] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.37 (s, 1H), 8.08 (dd, J = 8.0, 7.0 Hz, 1H), 7.72 (d, J = 8.0 Hz, 1H), 2.50 (s, 3H), 1.36 (s, 9H). 1-138 SO.sub.2 [00156] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.40 (s, 1H), 8.24 (dd, J = 8.0, 7.0 Hz, 1H), 7.98 (d, J = 8.0 Hz, 1H), 2.50 (s, 3H), 1.37 (s, 9H) 1-139 S CF.sub.2CF.sub.3 Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.41 (s, 1H), 8.14 (dd, J = 8.0, 7.0 Hz, 1H), 7.99 (d, J = 8.0 Hz, 1H), 2.51 (s, 3H). 1-140 S CF.sub.2CF.sub.2CF.sub.3 Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.42 (s, 1H), 8.20 (dd, J = 8.0, 7.0 Hz, 1H), 8.07 (d, J = 8.0 Hz, 1H), 2.51 (s, 3H). 1-141 S [00157] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.41 (s, 1H), 8.22 (dd, J = 8.0, 8.09 (d, J = 8.0 Hz, 1H), 3.27 (s, 6H), 2.51 (s, 3H). 1-142 S [00158] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.40 (s, 1H), 8.00 (dd, J = 8.0, 7.0 Hz, 1H), 7.89 (d, J = 8.0 Hz, 1H), 2.51 (s, 3H), 0.02 (s, 9H). 1-143 S [00159] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.41 (s, 1H), 8.05 (dd, J = 8.0, 7.0 Hz, 1H), 7.93 (d, J = 8.0 Hz, 1H), 2.50 (s, 3H), 2.31 (q, J = 7.5 Hz, 2H), 1.16 (t, J = 7.5 Hz, 3H). 1-144 S [00160] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.40 (s, 1H), 8.00 (dd, J = 8.0, 7.0 Hz, 1H), 7.89 (d, J = 8.0 Hz, 1H), 3.97 (t, J = 8.0 Hz, 2H), 3.36 (t, J = 8.0 Hz, 2H), 3.01 (s, 6H), 2.51 (s, 3H), 1-145 S [00161] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.41 (s, 1H), 8.20 (d, J = 2.0 Hz, 1H), 8.02 (dd, J = 8.0, 7.0 Hz, 1H), 7.93 (d, J = 8.0 Hz, 1H), 7.56 (d, J = 2.5 Hz, 1H), 6.89 (dd, J = 2.5, 2.0 Hz, 1H), 2.50 (s, 3H) 1-146 S [00162] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.41 (s, 1H), 8.08 (dd, J = 8.0, 7.0 Hz, 1H), 7.98-7.73 (m, 6H), 2.50 (s, 3H) 1-147 S [00163] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.40 (s, 1H), 8.77 (s, 1H), 8.06 (dd, J = 8.0, 7.0 Hz, 1H), 7.92 (d, J = 8.0 Hz, 1H), 3.77 (s, 3H), 2.50 (s, 3H), 2.47 (s, 3H). 1-148 S [00164] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.41 (s, 1H), 8.37 (s, 1H), 8.00 (dd, J = 8.0, 7.88 (d, J = 8.0 Hz, 1H), 4.35 (s, 2H), 3.75 (s, 3H), 2.50 (s, 3H), 2.10 (s, 3H). 1-149 NCOMe [00165] Me H 1-150 NSO.sub.2Me Me Me H 1-151 NPh Et Me H 1-152 NH CH.sub.2Ph Me H 1-153 NH [00166] Me H 1-154 [00167] Me Me H 1-155 [00168] Me Me H 1-156 [00169] Et Me H 1-157 S F Me H 1-158 O Cl Me H 1-159 SO Br Me H 1-160 SO.sub.2 I Me H 1-161 SO [00170] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.03 (dd, J = 7.5. 6.0 Hz, 1H), 7.62 (d, J = 7.5 Hz, 1H), 2.43 (s, 3H). 1-162 SO.sub.2 [00171] Me H 1-163 O [00172] Me H 1-164 S COOH Me H 1-165 S NO.sub.2 Me H 1-166 S NH.sub.2 Me H 1-167 S [00173] Me H 1-168 O [00174] Me H 1-169 NH [00175] Me H 1-170 SO [00176] Me H 1-171 SO.sub.2 [00177] Me H 1-172 S [00178] Me H 1-173 S [00179] Me H 1-174 S [00180] Me H 1-175 S [00181] Me H 1-176 S [00182] Me H 1-177 O [00183] Me H 1-178 NMe [00184] Me H 1-179 NH [00185] Me H 1-180 NH [00186] Me H 1-181 S [00187] Me H 1-182 S [00188] Me H 1-183 NH [00189] Me H 1-184 O [00190] Me H 1-185 S [00191] Me H 1-186 S [00192] Me H 1-187 S [00193] Me H 1-188 O [00194] Me H 1-189 NH [00195] Me H 1-190 SO [00196] Me H 1-191 O [00197] Me H 1-192 S [00198] Me H 1-193 S [00199] Me H 1-194 S [00200] Me H 1-195 S [00201] Me H 1-196 NH [00202] Me H 1-197 NH [00203] Me H 1-198 S [00204] Me H 1-199 SO [00205] Me H 1-200 SO.sub.2 [00206] Me H 1-201 O [00207] Me H 1-202 NEt [00208] Me H 1-203 NH [00209] Me H 1-204 S [00210] Me H 1-205 SO [00211] Me H 1-206 SO.sub.2 [00212] Me H 1-207 S [00213] Me H 1-208 SO [00214] Me H 1-209 SO.sub.2 [00215] Me H 1-210 O [00216] Me H 1-211 S [00217] Me H 1-212 O [00218] Me H 1-213 S [00219] Me H 1-214 S [00220] Me H 1-215 O [00221] Me H 1-216 S [00222] Me H 1-217 O [00223] Me H 1-218 SO [00224] Me H 1-219 SO.sub.2 [00225] Me H 1-220 S [00226] Me H 1-221 S [00227] Me H 1-222 S [00228] Me H 1-223 S [00229] Me H 1-224 NH [00230] Me H 1-225 S [00231] Me H 1-226 S [00232] Me H 1-227 S [00233] Me H 1-228 SO [00234] Me H 1-229 SO.sub.2 [00235] Me H 1-230 SO [00236] Me H 1-231 SO.sub.2 [00237] Me H 1-232 NH [00238] Me H 1-233 S [00239] Me H 1-234 O [00240] Me H 1-235 S [00241] Me H 1-236 S [00242] Me H 1-237 S [00243] Me H 1-238 O [00244] Me H 1-239 S [00245] Me H 1-240 SO [00246] Me H 1-241 S [00247] Me H 1-242 SO [00248] Me H 1-243 SO.sub.2 [00249] Me H 1-244 NH [00250] Me H 1-245 O [00251] Me H 1-246 S [00252] Me H 1-247 S [00253] Me H 1-248 S [00254] Me H 1-249 S [00255] Me H 1-250 S [00256] Me H 1-251 S [00257] Me H 1-252 S [00258] Me H 1-253 S [00259] Me H 1-254 SO [00260] Me H 1-255 SO.sub.2 [00261] Me H 1-256 SO [00262] Me H 1-257 SO.sub.2 [00263] Me H 1-258 SO [00264] Me H 1-259 SO.sub.2 [00265] Me H 1-260 S [00266] Me H 1-261 S [00267] Me H 1-262 S [00268] Me H 1-263 S [00269] Me H 1-264 O [00270] Me H 1-265 S [00271] Me H 1-266 SO [00272] Me H 1-267 S [00273] Me H 1-268 S [00274] Me H 1-269 S [00275] Me H 1-270 O [00276] Me H 1-271 NH [00277] Me H 1-272 S [00278] Me H 1-273 S [00279] Me H 1-274 S [00280] Me H 1-275 S [00281] Me H 1-276 S [00282] Me H 1-277 SO.sub.2 [00283] Me H 1-278 SO [00284] Me H 1-279 S [00285] Me H 1-280 O [00286] Me H 1-281 NH [00287] Me H 1-282 S [00288] Me H 1-283 S [00289] Me H 1-284 S [00290] Me H 1-285 S [00291] Me H 1-286 S [00292] Me H 1-287 S [00293] Me H 1-288 S [00294] Me H 1-289 S [00295] Me H 1-290 S [00296] Me H 1-291 S [00297] Me H 1-292 S [00298] Me H 1-293 SO.sub.2 [00299] Me H 1-294 SO [00300] Me H 1-295 S [00301] Me H 1-296 S [00302] Me H 1-297 S [00303] Me H 1-298 S [00304] Me H 1-299 S [00305] Me H 1-300 S [00306] Me H 1-301 S [00307] Me H 1-302 O [00308] Me H 1-303 NH [00309] Me H 1-304 S [00310] Me H 1-305 S [00311] Me H 1-306 SO.sub.2 [00312] Me H 1-307 SO [00313] Me H 1-308 SO.sub.2 [00314] Me H 1-309 SO [00315] Me H 1-310 S [00316] Me H 1-311 S [00317] Me H 1-312 [00318] Me H 1-313 [00319] Me H 1-314 [00320] Me H 1-315 [00321] Me H 1-316 [00322] Me H 1-317 [00323] Me H 1-318 [00324] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.36 (s, 1H), 7.72- 7.65 (m, 2H), 3.12- 3.09 (m, 4H), 2.47 (s, 3H), 1.74- 1.64 (m, 6H). 1-319 [00325] Me H 1-320 [00326] Me H 1-321 [00327] Me H 1-322 [00328] Me H 1-323 [00329] Me H 1-324 [00330] Me H 1-325 [00331] Me H 1-326 [00332] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.27 (s, 1H), 7.96- 7.82 (m, 2H), 7.65 (s, 1H), 7.42 (s, 1H), 2.47 (s, 3H), 2.08 (s, 3H). 1-327 [00333] Me H 1-328 [00334] Me H 1-329 [00335] Me H 1-330 [00336] Me H 1-331 [00337] Me H 1-332 [00338] Me H 1-333 [00339] Me H 1-334 [00340] Me H 1-335 [00341] Me H 1-336 [00342] Me H 1-337 [00343] Me H 1-338 [00344] Me H 1-339 [00345] Me H 1-340 S Et Me OMe 1-341 O Me Me [00346] 1-342 NMe Me Me [00347] 1-343 S Et Me [00348] 1-344 S Et Me [00349] 1-345 O Me Me [00350] 1-346 NMe Me Me [00351] 1-347 S Et Me [00352] 1-348 O Me Me [00353] 1-349 S Et Me [00354] 1-350 NMe Me Me [00355] 1-351 S Et Me [00356] 1-352 S Et Me [00357] 1-353 O Me Me [00358] 1-354 S Et Me [00359] 1-355 NMe Me Me [00360] 1-356 S Et Me [00361] 1-357 S Et Me [00362] 1-358 S Et Me [00363] 1-359 O Me Me [00364] 1-360 S Et Me [00365] 1-361 S Et Me [00366] 1-362 S Et Me [00367] 1-363 O Me Me [00368] 1-364 NMe Me Me [00369] 1-365 S Et Me [00370] 1-366 S Et Me [00371] 1-367 NMe Me Me [00372] 1-368 S Et Me [00373] 1-369 SO.sub.2 Et Me [00374] 1-370 O Me Me [00375] 1-371 S Et Me [00376] 1-372 S Et Me [00377] 1-373 SO Et Me [00378] 1-374 NMe Me Me [00379] 1-375 S Et Me [00380] 1-376 O Me Me [00381] 1-377 NMe Me Me [00382] 1-378 S Et Me [00383] 1-379 O Me Me [00384] 1-380 S Et Me [00385] 1-381 S Et Me [00386] 1-382 SO.sub.2 Et Me [00387] 1-383 NMe Me Me [00388] 1-384 O Me Me [00389] 1-385 S Et Me [00390] 1-386 SO Et Me [00391] 1-387 SO.sub.2 Et Me [00392] 1-388 S Et Me [00393] 1-389 S Et Me [00394] 1-390 S Et Me [00395] 1-391 S Et Me [00396] 1-392 SO [00397] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.33 (dd, J = 8.0, 7.0 Hz, 1H), 7.59 (d, J = 8.0 Hz, 1H), 2.64 (s, 2H), 2.46 (s, 3H), 0.94 (s, 9H). 1-393 SO [00398] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.34 (dd, J = 7.5, 6.0 Hz, 1H), 7.61 (d, J = 7.5 Hz, 1H), 2.76 (t, J = 8.0 Hz, 2H), 2.46 (s, 3H), 1.49 (t, J = 8.0 Hz, 2H), 0.86 (s, 9H). 1-394 SO [00399] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.55 (s, 1H), 8.10 (d, J = 7.5 Hz, 1H), 7.89- 7.86 (m, 1H), 2.47 (s, 3H), 2.21-2.19 (m, 1H), 1.90-1.79 (m, 1H), 1.71-1.63 (m, 1H), 1.62-1.56 (m, 1H), 1.49-1.41 (m, 1H), 1.38-1.10 (m, 6H). 1-395 SO [00400] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.34 (dd, Hz, 1H), 7.59 (d J= 7.5 Hz, 1H), 2.76 (t, J = 8.1 Hz, 2H), 2.46 (s, 3H), 1.55- 1.46 (m, 2H), 0.98-0.87 (m, 1H), 0.42- 0.31 (m, 2H), 0.24-0.18 (m, 2H). 1-396 SO [00401] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.33 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5, 1H), 2.76 (t, J = 5.2 Hz, 2H), 2.46 (s, 3H), 1.72- 1.43 (m, 7H), 1.40-1.29 (m, 3H), 1.29- 1.20 (m, 2H), 1.20- 1.15 (m, 1H). 1-397 SO [00402] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.33 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 5.87-5.76 (m, 1H), 5.08- 4.93 (m, 2H), 2.82 (t, J = 8.0 Hz, 2H), 2.46 (s, 3H), 2.34-2.26 (m, 2H). 1-398 SO [00403] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.38 (dd, J = 7.5, 6.0 Hz, 1H), 7.60 (d, J = 7.5 Hz, 1H), 5.55 2H), 3.45- 3.34 (m, 2H), 2.46 (s, 3H), 1.65-1.60 (m, 3H). 1-399 SO [00404] Me H 1-400 SO [00405] Me H 1-401 SO [00406] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.34 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 3.05 (t, J = 3.0 Hz, 1H), 2.95 (t, J = 8.0 Hz, 2H), 2.46 (s, 3H), 2.37- 2.26 (m, 2H). 1-402 SO [00407] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.32 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 3.47 (q, J = 2.0 Hz, 2H), 2.46 (s, 3H), 1.77 (t, J = 2.0 Hz, 3H). 1-403 SO [00408] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.33 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 4.35 (t, J = 7.5 Hz, 1H), 4.25 (t, J = 7.5 Hz, 1H), 2.76 (t, J = 5.5 Hz, 2H), 2.46 (s, 3H), 1.90- 1.76 (m, 2H). 1-404 SO [00409] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.28 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 5.20-5.11 (m, 1H), 3.04-2.93 (m, 1H), 2.79- 2.68 (m, 1H), 2.40 (s, 3H), 1.41 (dd, J = 25.0, 7.0 Hz, 3H). 1-405 SO [00410] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.34 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 5.37 (t, J = 7.0 Hz, 1H), 2.76 (t, J = 8.5 Hz, 2H), 2.46 (s, 3H), 1.99- 1.88 (m, 2H). 1-406 SO [00411] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.33 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 3.45- 3.32 (m, 2H), 2.46 (s, 3H), 1.63-1.51 (m, 3H). 1-407 SO [00412] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.32 (dd, J = 7.5, 6.0 Hz, 1H), 7.57 (d, J = 7.5 Hz, 1H), 2.45 (s, 3H). 1-408 SO [00413] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.31 (dd, Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 2.45 (s, 3H). 1-409 SO [00414] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.36 (dd, J = 7.5, 6.0 Hz, 1H), 7.61 (d, J = 7.5 Hz, 1H), 2.46 (s, 3H). 1-410 SO [00415] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.35 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 2.45 (s, 3H). 1-411 SO [00416] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.34 (dd, J = 7.5, 6.0 Hz, 1H), 7.61 (d, J = 7.5 Hz, 1H), 2.76 (t, J = 8.0 Hz, 2H), 2.52- 2.40 (m, 5H), 1.38-1.27 (m, 2H). 1-412 SO [00417] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.42 (dd, J = 7.5, 6.0 Hz, 1H), 7.60 (d, J = 7.5 Hz, 1H), 2.76 (t, J = 8.5 Hz, 2H), 2.46 (s, 3H), 1.93- 1.82 (m, 2H). 1-413 SO [00418] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.37 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 2.76 (t, J = 8.0 Hz, 2H), 2.46 (s, 3H), 1.71 (dt, J = 25.0, 8.0 Hz, 2H). 1-414 SO [00419] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.33 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 3.57 (t, J = 7.5 Hz, 2H), 2.76 (t, J = 5.5 Hz, 2H), 2.46 (s, 3H), 1.91- 1.80 (m, 2H). 1-415 SO [00420] Me H 1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.33 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 4.76- 4.64 (m, 1H), 3.13 (dd, J = 12.5, 7.0 Hz, 1H), 2.88 (dd, J = 12.5, 7.0 Hz, 1H), 2.46 (s, 3H), 1.55 (d, J = 7.0 Hz, 3H). 1-416 SO [00421] Me H 1-417 SO [00422] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.33 (dd, J = 7.5, 6.0 Hz, 1H), 7.56 (d, J = 7.5 Hz, 1H), 6.01 (t, J = 6.0 Hz, 1H), 3.45 (d, J = 6.0 Hz, 2H), 2.46 (s, 3H). 1-418 SO [00423] Me H 1-419 SO [00424] Me H 1-420 SO [00425] Me H 1-421 SO [00426] Me H 1-422 SO [00427] Me H 1-423 SO [00428] Me H 1-424 SO [00429] Me H 1-425 SO [00430] Me H 1-426 SO [00431] Me H 1-427 SO [00432] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.35 (dd, J = 7.5, 6.0 Hz, 1H), 7.60 (d, J = 7.5 Hz, 1H), 3.15 (t, J = 8.0 Hz, 2H), 2.55 (t, J = 8.0 Hz, 2H), 2.46 (s, 3H). 1-428 SO [00433] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.34 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 2.76 (t, J = 5.0 Hz, 2H), 2.46 (s, 3H), 2.14 (t, J = 5.5 Hz, 2H), 2.00 (1), J = 5.5 Hz, 2H). 1-429 SO [00434] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.33 (dd, J = 7.5, 6.0 Hz, 1H), 7.60 (d, J = 7.5 Hz, 1H), 4.27 (t, J = 5.0 Hz, 1H), 3.87- 3.72 (m, 2H), 2.97 (t, J = 4.0 Hz, 2H), 2.46 (s, 3H). 1-430 SO [00435] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.34 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 4.34 (t, J = 5.0 Hz, 1H), 3.50 (q, J = 5.0 Hz, 2H), 2.76 (t, J = 8.0 Hz, 2H), 2.46 (s, 3H), 1.82- 1.71 (m, 2H). 1-431 SO [00436] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.34 (dd, J = 7.5, 6.0 Hz, 1H), 7.60 (d, J = 7.5 Hz, 1H), 5.24-5.15 (m, 1H), 4.34 (d, J = 5.0 Hz, 1H), 4.41 (d, J = 5.0 Hz, 2H), 3.12 (d, J = 7.0 Hz, 2H), 2.46 (s, 3H). 1-432 SO [00437] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.33 (dd, J = 7.5, 6.0 Hz, 1H), 7.61 (d, J = 7.5 Hz, 1H), 3.08- 2.93 (m, 4H), 3.01- 2.95 (m, 2H), 2.60 (s, 2H), 2.46 (s, 3H). 1-433 SO [00438] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.35 (dd, J = 7.5, 6.0 Hz, 1H), 7.61 (d, J = 7.5 Hz, 1H), 4.96 (s, 1H), 2.81 (q, J = 8.0 Hz, 2H), 2.46 (s, 3H), 0.87 (t, J = 8.0 Hz, 3H). 1-434 SO [00439] Me H 1-435 SO [00440] Me H 1-436 SO [00441] Me H 1-437 SO [00442] Me H 1-438 SO [00443] Me H 1-439 SO [00444] Me H 1-440 SO [00445] Me H 1-441 SO [00446] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.34 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 4.04-3.92 (m, 2H), 3.85- 3.72 (m, 2H), 2.46 (s, 3H), 2.32 (s, 3H), 1.97 (s, 1H). 1-442 SO [00447] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.34 (dd, J = 7.5, 6.0 Hz, 1H), 7.60 (d, J = 7.5 Hz, 1H), 3.57 (q, J = 8.0 Hz, 2H), 2.46 (s, 3H), 1.15 (t, J = 8.0 Hz, 3H). 1-443 SO [00448] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.32 (dd, J = 7.5, 6.0 Hz, 1H), 7.61- 7.55 (m, 1H), 4.86- 4.73 (m, 2H), 3.21 (s, 3H), 2.46 (s, 3H). 1-444 SO [00449] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.34 (dd, J = 7.5, 6.0 Hz, 1H), 7.61 (d, J = 7.5 Hz, 1H), 3.71 (t, J = 7.5 Hz, 1H), 3.43 (q, J = 8.0 Hz, 2H), 2.95 (t, J = 7.5 Hz, 1H), 2.45 (s, 3H), 1.08 (t, J = 8.0 Hz, 3H). 1-445 SO [00450] Me H .sup.1H NMR (500 MHz, DMSO-d6) 12.41 (s, 1H), 8.12 (dd, J = 8.0, 7.0 Hz, 1H), 7.83 (d, J = 8.0 Hz, 1H), 4.35-4.24 (m, 1H), 3.32 (s, 3H), 2.50 (s, 3H), 1.45 (d, J = 7.5 Hz, 3H) 1-446 SO [00451] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.32 (dd, J = 7.5, 6.0 Hz, 1H), 7.58 (d, J = 7.5 Hz, 1H), 4.86-4.73 (m, 2H), 4.56- 4.43 (m, 2H), 3.46 (q, J = 8.0 Hz, 2H), 2.46 (s, 3H), 1.03 (t, J = 8.0 Hz, 3H). 1-447 SO [00452] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.34 (dd, J = 7.5, 6.0 Hz, 1H), 7.64- 7.58 (m, 1H), 3.70- 3.61 (m, 1H), 3.22 (s, 3H), 3.02 (dd, J = 12.0, 7.0 Hz, 1H), 2.77 (dd, J = 12.0, 7.0 Hz, 1H), 2.46 (s, 3H), 1.18 (d, J = 7.0 Hz, 3H). 1-448 SO [00453] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.33 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 3.34 (t, J = 7.5 Hz, 2H), 3.18 (s, 3H), 2.76 (t, J = 5.5 Hz, 2H), 2.46 (s, 3H), 1.80- 1.71 (m, 2H). 1-449 SO [00454] Me H 1-450 SO [00455] Me H 1-451 SO [00456] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.34 (s, 1H), 8.07- 8.95 (m, 1H), 7.59 (d, J = 8.0 Hz, 1H), 3.89- 3.80 (m, 1H), 3.02- 2.95 (m, 1H), 2.81- 2.72 (m, 2H), 2.47 (s, 3H), 2.44- 2.39 (m, 1H). 1-452 SO [00457] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 7.78 (dd, J = 7.5, 6.0 Hz, 1H), 7.60 (d, J = 7.5 Hz, 1H), 4.75 (dd, J = 7.0 6.0 Hz, 2H), 4.51 (dd, J = 7.0, 6.0 Hz, 2H), 3.28- 3.17 (m, 1H), 2.70 (d, J = 7.0 Hz, 2H), 2.45 (s, 3H). 1-453 SO [00458] Me H 1-454 SO [00459] Me H 1-455 SO [00460] Me H 1-456 SO [00461] Me H 1-457 SO [00462] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.01 (s, 1H), 8.23- 8.10 (m, 1H), 7.93 (d, J = 8.0 Hz, 1H), 7.65- 7.46 (m, 5H), 2.48 (s, 3H). 1-458 SO [00463] Me H 1-459 SO [00464] Me H 1-460 SO [00465] Me H 1-461 SO [00466] Me H 1-462 SO [00467] Me H 1-463 SO [00468] Me H 1-464 SO [00469] Me H 1-465 SO [00470] Me H 1-466 SO [00471] Me H 1-467 SO [00472] Me H 1-468 SO [00473] Me H 1-469 SO [00474] Me H 1-470 SO [00475] Me H 1-471 SO [00476] Me H 1-472 SO [00477] Me H 1-473 SO [00478] Me H 1-474 SO [00479] Me H 1-475 SO [00480] Me H 1-476 SO [00481] Me H 1-477 SO [00482] Me H 1-478 SO [00483] Me H 1-479 SO [00484] Me H 1-480 SO [00485] Me H 1-481 SO [00486] Me H 1-482 SO [00487] Me H 1-483 SO [00488] Me H 1-484 SO [00489] Me H 1-485 SO [00490] Me H 1-486 SO [00491] Me H 1-487 SO [00492] Me H 1-488 SO [00493] Me H 1-489 SO [00494] Me H 1-490 SO [00495] Me H 1-491 SO [00496] Me H 1-492 SO [00497] Me H 1-493 SO [00498] Me H 1-494 SO [00499] Me H 1-495 SO [00500] Me H 1-496 SO [00501] Me H 1-497 SO [00502] Me H 1-498 SO [00503] Me H 1-499 SO [00504] Me H 1-500 SO [00505] Me H 1-501 SO [00506] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.59 (s, 1H) 8.10- 7.91 (m, 4H), 7.17 (d, J = 6.5 Hz, 2H), 2.47 (s, 3H). 1-502 SO [00507] Me H 1-503 SO [00508] Me H 1-504 SO [00509] Me H 1-505 SO [00510] Me H 1-506 SO [00511] Me H 1-507 SO [00512] Me H 1-508 SO [00513] Me H 1-509 SO [00514] Me H 1-510 SO [00515] Me H 1-511 SO [00516] Me H 1-512 SO [00517] Me H 1-513 SO [00518] Me H 1-514 SO [00519] Me H 1-515 SO [00520] Me H 1-516 SO [00521] Me H 1-517 SO [00522] Me H 1-518 SO [00523] Me H 1-519 SO [00524] Me H 1-520 SO [00525] Me H 1-521 SO [00526] Me H 1-522 SO [00527] Me H 1-523 SO [00528] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.27 (dd, J = 7.5, 6.0 Hz, 1H), 7.58 (d, J = 7.5 Hz, 1H), 7.15 (t, J = 50.0 Hz, 1H), 3.71 (t, J = 8.0 Hz, 2H), 2.95 (t, J = 8.0 Hz, 2H), 2.40 (s, 3H). 1-524 SO [00529] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.34 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 3.71.-3.62 (m, 2H), 2.95 (t, J = 8.0 Hz, 2H), 2.46 (s, 3H). 1 -525 SO [00530] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.33 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 3.87-3.75 (m, 2H), 2.97 (t, J = 4.5 Hz, 2H), 2.46 (s, 3H), 2.42 (s, 6H). 1-526 SO [00531] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.34 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 2.48- 2.40 (m, 2H), 1.26 (t, J = 8.0 Hz, 3H). 1-527 SO [00532] Me H 1-528 SO [00533] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.34 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 2.92 (q, J = 45.0 Hz, 2H), 2.45 (s, 3H). 1-529 SO [00534] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.10- 8.03 (m, 2H), 7.79 (dd, J = 7.5, 6.0 Hz, 1H), 7.67- 7.54 (m, 1H), 7.61-7.51 (m, 3H), 2.45 (s, 3H). 1-530 SO [00535] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.35 (dd, J = 7.5, 6.0 Hz, 1H), 7.84 (d, J = 7.5 Hz, 1H), 7.60 (dd, J = 7.5 Hz, 1H), 7.52 (dd, J = 7.5, 1.5 Hz, 1H), 6.74 (t, J = 7.5 Hz, 1H), 2.46 (s, 3H). 1-531 SO [00536] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.35 (dd, J = 7.5, 6.0 Hz, 1H), 8.24 (s, 1H), 7.60 (d, J = 7.5 Hz, 1H), 3.81 (s, 3H), 2.60 (s, 3H), 2.46 (s, 3H). 1-532 SO [00537] Me H 1-533 SO [00538] Me H 1-534 SO [00539] Me H 1-535 SO [00540] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.34 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 3.06 (s, 6H), 2.45 (s, 3H). 1-536 SO [00541] Me H 1-537 SO [00542] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.06 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 3.67 (s, 2H), 2.91 (s, 6H), 2.46 (s, 3H). 1-538 SO [00543] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 7.77 (dd, J = 7.5, 6.0 Hz, 1H), 7.60- 7.55 (m, 1H), 4.73 (s, 2H), 3.06 (s, 9H), 2.45 (s, 3H). 1-539 SO [00544] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.67 (s, 1H), 8.16- 8.05 (m, 1H), 7.78 (d, J = 8.0 Hz, 1H), 7.30- 7.16 (m, 5H), 4.78- 4.63 (m, 2H), 2.47 (s, 3H). 1-540 SO [00545] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.55 (s, 1H), 8.10- 8.01 (m, 1H), 7.87 (d, J = 8.0 Hz, 1H), 7.35- 7.26 (m, 4H), 7.27- 7.20 (m, 1H), 3.88- 3.77 (m, 1H), 3.48- 3.40 (m, 1H), 3.18- 3.08 (m, 1H), 3.02- 2.92 (m, 1H), 2.48 (s, 3H). 1-541 SO [00546] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.59 (s, 1H), 8.14- 8.02 (m, 1H), 7.87- 7.82 (m, 1H), 7.62- 7.59 (m, 1H), 6.39- 6.34 (m, 2H), 4.97- 4.86 (m, 1H), 4.84- 4.75 (m, 1H), 2.47 (s, 3H). 1-542 SO [00547] Me H 1-543 SO [00548] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 8.34 (dd, J = 7.5, 6.0 Hz, 1H), 7.60 (d, J = 7.5 Hz, 1H), 6.88 (s, 1H), 4.70 (s, 2H), 3.72 (s, 3H), 2.46 (s, 3H), 2.29 (s, 3H). 1-544 SO [00549] Me H 1-545 SO [00550] Me H 1-546 SO [00551] Me H 1-547 SO [00552] Me H 1-548 SO [00553] Me H 1-549 SO [00554] Me H 1-550 SO [00555] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 9.72 (t, J = 6.0 Hz, 1H), 8.39 (dd, J = 7.5, 6.0 Hz, 1H), 7.60 (d, J = 7.5 Hz, 1H), 3.89-3.78 (m, 2H), 2.46 (s, 3H). 1-551 SO [00556] Me H .sup.1H NMR (500 MHz, DMSO-d6) δ 12.38 (s, 1H), 9.90 (t, J = 6.0 Hz, 1H), 8.34 (dd, J = 7.5, 6.0 Hz, 1H), 7.61 (d, J = 7.5 Hz, 1H), 3.11-3.01 (m, 2H), 2.74- 2.61 (m, 2H), 2.46 (s, 3H). 1-552 SO [00557] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.34 (dd, J = 7.5, 6.0 Hz, 1H), 7.57 (d, J = 7.5 Hz, 1H), 3.94-3.83 (m, 2H), 2.45 (s, 3H), 2.16 (s, 3H). 1-553 SO [00558] Me H 1-554 SO [00559] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.41 (s, 1H), 12.38 (s, 1H), 8.18 (dd, J = 7.5, 6.0 Hz, 1H), 7.61 (d, J = 7.5 Hz, 1H), 3.72-3.63 (m, 2H), 2.46 (s, 3H). 1-555 SO [00560] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.33 (dd, J = 7.5, 6.0 Hz, 1H), 7.61 (d, J = 7.5 Hz, 1H), 4.31-4.23 (m, 2H), 3.73 (s, 3H), 2.47 (s, 3H). 1-556 SO [00561] Me H 1-557 SO [00562] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.35 (dd, J = 7.5, 6.0 Hz, 1H), 7.60 (d, J = 7.5 Hz, 1H), 4.31-4.22 (m, 2H), 2.46 (s, 3H), 1.39 (s, 9H). 1-558 SO [00563] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.33 (dd, J = 7.5, 6.0 Hz, 1H), 7.63-7.57 (m, 1H), 4.31-4.22 (m, 2H), 4.02- 3.86 (m, 4H), 4.17 (q, J = 8.0 Hz, 2H), 2.46 (s, 3H), 1.12 (t, J = 8.0 Hz, 3H). 1-559 SO [00564] Me H 1-560 SO [00565] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.35 (dd, J = 7.5, 6.0 Hz, 1H), 7.60 (d, J = 7.5 Hz, 1H), 4.31-4.22 (m, 2H), 2.46 (s, 3H), 1.39 (s, 9H). 1-561 SO [00566] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.29 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 3.93-3.82 (m, 2H), 2.45 (s, 3H), 2.21 (s, 3H). 1-562 SO [00567] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.34 (dd, J = 7.5, 6.0 Hz, 1H), 7.60 (d, J = 7.5 Hz, 1H), 3.15 (t, J = 8.0 Hz, 2H), 2.67 (t, J = 8.0 Hz, 2H), 2.46 (s, 3H), 2.07 (s, 3H) 1-563 SO [00568] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.24 (dd, J = 7.5, 6.0 Hz, 1H), 7.56 (d, J = 7.5 Hz, 1H), 4.06-3.91 (m, 2H), 2.53 (s, 3H), 2.45 (s, 3H). 1-564 SO [00569] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.03 (dd, J = 7.5, 6.0 Hz, 1H), 7.62 (d, J = 7.5 Hz, 1H), 2.63 (s, 3H), 0.08 (s, 9H). 1-565 SO [00570] Me H 1-566 SO [00571] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.32 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 4.13-4.01 (m, 2H), 3.02 (t, J = 3.5 Hz, 2H), 2.46 (s, 3H), 1.03 (s, 9H), 0.21 (s, 6H). 1-567 SO [00572] Me H .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1H), 8.33 (dd, J = 7.5, 6.0 Hz, 1H), 7.59 (dd, J = 7.5 Hz, 1H), 7.36-7.25 (m, 5H), 4.86 (s, 2H), 4.68 (s, 2H), 2.48 (s, 3H). 1-568 SO Et Me Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.96 (dd, J = 7.5, 6.0 Hz, 1H), 7.57 (d, J = 7.5 Hz, 1H), 3.25 (s, 3H), 2.82 (q, J = 8.0 Hz, 2H), 2.45 (s, 3H), 1.33 (t, J = 8.0 Hz, 3H). 1-569 SO Et Me Et 1-570 SO Et Me [00573] 1-571 SO Et Me [00574] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.79 (dd, J = 7.5, 6.0 Hz, 1H), 7.54 (d, J = 7.5 Hz, 1H), 5.93- 5.85 (m, 1H), 5.10- 5.01 (m, 1H), 4.89- 4.79 (m, 1H), 4.47- 4.43 (m, 2H), 2.85 (q, J = 8.0 Hz, 2H), 2.46 (s, 3H), 1.31 (t, J = 8.0 Hz, 3H). 1-572 SO Et Me [00575] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.81 (dd, J = 7.5, 6.0 Hz, 1H), 7.57 (d, J = 7.5 Hz, 1H), 3.94 (d, J = 3.0 Hz, 2H), 3.29 (t, J = 3.0 Hz, 1H), 2.84 (q, J = 8.0 Hz, 2H), 2.46 (s, 3H), 1.32 (t, J = 8.0 Hz, 3H). 1-573 SO Et Me [00576] 1-574 SO Et Me [00577] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.66 (dd, J = 7.5, 6.0 Hz, 1H), 7.55- 7.49 (m, 1H), 2.88 (q, J = 8.0 Hz, 2H), 2.46 (s, 3H), 2.22 (s, 3H), 1.34 (t, J = 8.0 Hz, 3H). 1-575 SO Et Me [00578] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.10 (dd, J = 7.5, 6.0 Hz, 1H), 7.91- 7.84 (m, 2H), 7.63-7.56 (m, 2H), 7.52 (t, J = 7.5 Hz, 2H), 2.81 (q, J = 8.0 Hz, 2H), 2.33 (s, 3H), 1.32 (t, J = 8.0 Hz, 3H). 1-576 SO Et Me [00579] 1-577 SO Et Me [00580] 1-578 SO Et Me [00581] 1-579 SO Et Me [00582] 1-580 SO Et Me [00583] 1-581 SO Et Me [00584] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.03 (dd, J = 7.5, 6.0 Hz, 1H), 7.62 (d, J = 7.5 Hz, 1H), 7.50 (s, 1H), 3.64 (s, 3H), 2.83 (q, J = 8.0 Hz, 2H), 2.63 (s, 3H), 2.46 (s, 3H), 1.17 (t, J = 8.0 Hz, 3H). 1-582 SO Et Me [00585] 1-583 SO Et Me [00586] 1-584 SO Et Me [00587] 1-585 SO Et Me [00588] 1-586 SO Et Me [00589] 1-587 SO Et Me [00590] 1-588 SO Et Me [00591] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.11 (dd, J = 7.5, 6.0 Hz, 1H), 7.61 (d, J = 7.5 Hz, 1H), 3.71 (s, 3H), 2.84 (q, J = 8.0 Hz, 2H), 2.46 (s, 3H), 1.33 (t, J = 8.0 Hz, 3H). 1-589 SO Et Me [00592] 1-590 SO Et Me [00593] 1-591 SO Et Me [00594] 1-592 SO Et Me [00595] 1-593 SO Et Me [00596] 1-594 SO Et Me [00597] 1-595 SO Et Me [00598] 1-596 SO Et Me [00599] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.11 (dd, J = 7.5, 6.0 Hz, 1H), 7.62 (d, J = 7.5 Hz, 1H), 3.52 (t, J = 4.5 Hz, 4H), 3.12 (t, J = 4.5 Hz, 4H), 2.85 (q, J = 8.0 Hz, 2H), 2.44 (s, 3H), 1.30 (t, J = 8.0 Hz, 3H). 1-597 SO Et Me [00600] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.94 (dd, J = 7.5, 6.0 Hz, 1H), 7.57 (d, J = 7.5 Hz, 1H), 3.72 (q, J = 9.0 Hz, 2H), 2.82 (q, J = 8.0 Hz, 2H), 2.46 (s, 3H), 1.31 (t, J = 8.0 Hz, 3H). 1-598 SO Et Me [00601] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.90 (dd, J = 7.5, 6.0 Hz, 1H), 7.61 (d, J = 7.5 Hz, 1H), 4.32 (s, 2H), 2.83 (q, J = 8.0 Hz, 2H), 2.47 (s, 3H), 1.31 (t, J = 8.0 Hz, 3H). 1-599 SO Et Me [00602] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.67 (dd, J = 7.5, 6.0 Hz, 1H), 7.40 (d, J = 7.5 Hz, 1H), 7.28- 7.19 (m, 5H), 5.03 (s, 2H), 2.85 (q, J = 8.0 Hz, 2H), 2.47 (s, 3H), 1.27 (t, J = 8.0 Hz, 3H). 1-600 SO Et Me [00603] 1-601 SO Et Me [00604] 1-602 SO Et Me [00605] 1-603 SO Et Me [00606] 1-604 SO Et Me [00607] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.87 (dd, J = 7.5, 6.0 Hz, 1H), 7.66 (d, J = 7.5 Hz, 1H), 6.28 (q, J = 7.5 Hz, 1H), 3.81 (s, 3H), 2.83 (q, J = 8.0 Hz, 2H), 2.46 (s, 3H), 1.64 (d, J = 7.0 Hz, 3H), 1.31 (t, J = 8.0 Hz, 3H). 1-605 SO [00608] Me Me 1-606 SO [00609] Me [00610] 1-607 SO [00611] Me [00612] 1-608 SO [00613] Me [00614] 1-609 SO [00615] Me [00616] 1-610 SO [00617] Me [00618] 1-611 SO [00619] Me [00620] 1-612 SO [00621] Me [00622] 1-613 SO [00623] Me [00624] 1-614 SO [00625] Me [00626] 1-615 SO [00627] Me [00628] 1-616 SO [00629] Me [00630] 1-617 SO [00631] Me [00632] .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.82 (dd, J = 7.5, 6.0 Hz, 1H), 7.56 (d, J = 7.5 Hz, 1H), 6.31 (q, J = 7.0 Hz, 1H), 4.70- 4.53 (m, 2H), 3.50 (td, J = 12.5, 3.0 Hz, 1H), 3.24 (td, J = 12.5, 3.0 Hz, 1H), 2.56- 2.42 (m, 1H), 2.36 (s, 3H), 1.67- 1.52 (m, 4H), 1.32 (t, J = 8.0 Hz, 3H), 0.88 (t, J = 8.0 Hz, 3H). 1-618 SO [00633] Me [00634] 1-619 SO [00635] Me [00636] 1-620 SO [00637] Me [00638] 1-621 SO [00639] Me [00640] 1-622 SO [00641] Me [00642] 1-623 SO [00643] Me [00644] 1-624 SO [00645] Me [00646] 1-625 SO [00647] Me [00648] 1-626 SO [00649] Me [00650] 1-627 SO [00651] Me [00652] 1-628 SO [00653] Me [00654] 1-629 SO [00655] Me [00656] 1-630 SO [00657] Me [00658] 1-631 SO [00659] Me [00660] 1-632 SO [00661] Me [00662] 1-633 SO [00663] Me [00664] 1-634 SO [00665] Me [00666] 1-635 SO [00667] Me [00668] 1-636 SO [00669] Me [00670] 1-637 SO [00671] Me [00672] 1-638 SO [00673] Me [00674] 1-639 SO [00675] Me [00676] 1-640 SO [00677] Me [00678] 1-641 SO [00679] Me [00680] 1-642 SO [00681] Me [00682] 1-643 SO [00683] Me [00684] 1-644 SO [00685] Me [00686] 1-645 SO [00687] Me [00688] 1-646 SO [00689] Me [00690] 1-647 SO [00691] Me [00692] 1-648 SO [00693] Me [00694] 1-649 SO [00695] Me [00696] 1-650 SO [00697] Me [00698] 1-651 SO [00699] Me OMe 1-652 SO [00700] Me [00701] 1-653 SO [00702] Me [00703] 1-654 SO [00704] Me [00705] 1-655 SO [00706] Me [00707] 1-656 SO [00708] Me [00709] 1-657 SO [00710] Me [00711] 1-658 SO [00712] Me [00713] 1-659 SO [00714] Me [00715] 1-660 SO [00716] Me [00717] 1-661 SO [00718] Me [00719]

[0162] Table A2 is constructed in the same manner as Table A1 except that the fourth column (i.e., “Z” column) are replaced by the corresponding “Z” column shown below. Accordingly, the first column in Table A2 is the number of compound (Compound No.), i.e., Compound 2-1 (wherein, X is S, Y is Me, Z is Et, and M is H), followed by Compound 2-2, Compound 2-3, and Compound 2-4, the last number of compound is Compound 2-661.

TABLE-US-00002 Table “Z” A2  Et A3  H A4  [00720] A5  I A6  [00721] A7  Br A8  [00722] A9  F A10  [00723] A11  [00724] A12  [00725] A13  [00726] A14  [00727] A15  [00728] A16  Cl A17  [00729] A18  CN A19  [00730] A20  CF.sub.3 A21  [00731] A22  [00732] A23  [00733] A24  [00734] A25  [00735] A26  [00736] A27  [00737] A28  [00738] A29  [00739] A30  [00740] A31  [00741] A32  [00742] A33  [00743] A34  [00744] A35  [00745] A36  [00746] A37  [00747] A38  [00748] A39  [00749] A40  [00750] A41  [00751] A42  [00752] A43  [00753] A44  [00754] A45  [00755] A46  [00756] A47  [00757] A48  [00758] A49  [00759] A50  [00760] A51  [00761] A52  [00762] A53  [00763] A54  [00764] A55  [00765] A56  [00766] A57  [00767] A58  [00768] A59  [00769] A60  [00770] A61  [00771] A62  [00772] A63  [00773] A64  [00774] A65  [00775] A66  [00776] A67  [00777] A68  [00778] A69  [00779] A70  [00780] A71  [00781] A72  [00782] A73  [00783] A74  [00784] A75  [00785] A76  [00786] A77  [00787] A78  [00788] A79  [00789] A80  [00790] A81  [00791] A82  [00792] A83  [00793] A84  [00794] A85  [00795] A86  [00796] A87  [00797] A88  [00798] A89  [00799] A90  [00800] A91  [00801] A92  [00802] A93  [00803] A94  [00804] A95  [00805] A96  CHF.sub.2 A97  [00806] A98  [00807] A99  CH.sub.2F A100 [00808] A101 [00809] A102 [00810] A103 [00811] A104 SMe A105 [00812] A106 SO.sub.2Me A107 SOMe A108 [00813] A109 [00814] A110 COOEt A111 [00815] A112 [00816] A113 [00817] A114 [00818] A115 [00819] A116 [00820] A117 [00821] A118 [00822] A119 [00823] A120 [00824] A121 [00825] A122 [00826] A123 [00827] A124 [00828] A125 [00829] A126 [00830] A127 [00831] A128 [00832] A129 [00833] A130 [00834] A131 [00835] A132 [00836] A133 [00837] A134 [00838] A135 [00839] A136 [00840] A137 [00841] A138 NH.sub.2 A139 [00842] A140 [00843] A141 [00844] A142 [00845] A143 [00846] A144 [00847] A145 [00848] A146 [00849] A147 [00850] A148 [00851] A149 [00852] A150 [00853] A151 [00854] A152 [00855]

[0163] The .sup.1H NMR data of some of the compounds in the above tables are shown in Table 1:

TABLE-US-00003 TABLE 1 .sup.1H NMR data of compounds Compound No. .sup.1HNMR 2-3 .sup.1HNMR (500 MHz, DMSO-d6) 12.37 (s, 1 H), 8.23 (dd, J = 8.0, 7.0 Hz, 1 H), 7.98 (d, J = 8.0 Hz, 1 H), 3.45 (s, 3 H), 2.63 (q, J = 8.0 Hz, 2 H), 1.32 (t, J = 8.0 Hz, 3 H) 2-4 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.38 (s, 1 H), 7.88 (dd, J = 8.0, 7.0 Hz, 1 H), 7.78 (d, J = 8.0 Hz, 1 H), 2.98 (q, J = 7.5 Hz, 2 H), 2.71 (q, J = 7.0 Hz, 2 H), 1.15 (t, J = 7.5 Hz, 3 H), 1.10 (t, J = 7.5 Hz, 3 H). 2-8 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1 H),8.24 (dd, J = 7.5, 6.0 Hz, 1 H), 7.65 (d, J = 7.5 Hz, 1 H), 2.76 (t, J = 5.0 Hz, 2 H), 2.59 (q, J = 8.0 Hz, 2 H), 1.47-1.38 (m, 2 H), 1.13 (t, J = 8.0 Hz, 3 H), 0.94 (t, J = 8.0 Hz, 3 H). 3-4 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.68 (s, 1 H), 9.06 (s, 1 H), 7.89-7.83 (m, 1 H), 7.76 (d, J = 8.0 Hz, 1 H), 3.00-2.92 (m, 2 H), 1.13 (t, J = 7.5 Hz, 3 H). 3-5 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.72 (s, 1 H), 9.06 (s, 1 H), 8.18-8.04 (m, 1 H), 7.86 (d, J = 8.0 Hz, 1 H), 3.51-3.44 (m, 1 H), 3.29-3.22 (m, 1 H), 1.17 (t, J = 7.5 Hz, 3 H). 3-8 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1 H),8.24 (dd, J = 7.5, 6.0 Hz, 1 H), 7.71 (s, 1 H), 7.65 (d, J = 7.5 Hz, 1 H), 2.76 (t, J = 5.0 Hz, 2 H), 1.47-1.44 (m, 2 H), 0.95 (t, J = 8.0 Hz, 3 H). 3-11 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.58 (s, 1 H), 9.03 (s, 1 H), 8.19-8.08 (m, 1 H), 7.59 (d, J = 8.0 Hz, 1 H), 3.86-3.74 (m, 1 H), 1.43 -1.09 (m, 6 H). 3-14 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.78 (s, 1 H), 9.07 (s, 1 H), 8.14-8.06 (m, 1 H), 7.76 (d, J = 8.0 Hz, 1 H), 3.58-3.47 (m, 1 H), 3.20 ? 3.10 (m, 1 H), 1.73-1.51 (m, 2 H), 1.50-1.35(m, 2 H), 0.88 (t, J = 7.5 Hz, 3 H). 3-17 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.61 (s, 1 H), 9.08 (s, 1 H), 8.01-7.92 (m, 1 H), 7.59 (d, J = 8.0 Hz, 1 H), 2.75-2.68 (m, 1 H), 1.78-1.69 (m, 2 H), 1.40 (d, J = 7.0 Hz, 3 H), 0.94 (t, J = 8.0 Hz, 3 H). 3-20 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.77 (s, 1 H), 9.02 (s, 1 H), 8.13-8.03 (m, 1 H), 7.86 (d, J 8.0 Hz, 1 H), 3.59-3.48 (m, 1 H), 2.90-2.81 (m, 1 H), 2.19-2.04 (m, 1 H), 1.11-0.99 (m, 6 H). 3-52 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.67 (s, 1 H), 9.05 (s, 1 H), 8.27-8.18 (m, 1 H), 7.92 (d J = 8.0 Hz, 1 H), 2.76-2.62 (m, 2 H), 2.15-2.05 (m, 2 H). 3-54 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.71 (s, 1 H), 9.01 (s, 1 H), 8.03-7.93 (m, 1 H), 7.82 (d, J 8.0 Hz, 1 H), 3.78 (t, J = 8.0 Hz, 2 H), 3.07 (t, J = 8.0 Hz, 2 H). 3-57 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.67 (s, 1 H), 8.08-7.97 (m, 1 H), 7.74 (d, J = 8.0 Hz, 1 H), 3.81-3.71 (m, 1 H), 3.69-3.60 (m, 2 H), 3.42-3.35 (m, 1 H), 3.23 (s, 3 H). 4-4 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.40 (s, 1 H), 7.89 (dd, J = 8.0, 7.0 Hz, 1 H), 7.79 (d, J = 8.0 Hz, 1 H), 2.99 (q, J = 7.5 Hz, 2 H), 2.77 (t, J = 7.5 Hz, 2 H), 1.37-1.32 (m, 2 H), 1.15 (t, J = 7.5 Hz, 3 H), 1.06 (t, J = 7.0 Hz, 3 H). 4-8 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1 H),8.32 (dd, J = 7.5, 6.0 Hz, 1 H), 7.67 (d, J = 7.5 Hz, 1 H), 2.76 (t, J = 8.0 Hz, 2 H), 2.53 (t, J = 8.0 Hz, 2 H), 1.61-1.55 (m, 2 H), 1.47-1.33 (m, 2 H), 0.87- 0.83 (m, 6 H). 6-4 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.42 (s, 1 H), 7.91 (dd, J = 8.0, 7.0 Hz, 1 H), 7.80 (d, J = 8.0 Hz, 1 H), 3.01 (q, J = 7.5 Hz, 2 H), 2.97 (hept., J = 7.0 Hz, 1 H), 1.15 (t, J = 7.5 Hz, 3 H), 1.13 (d, J = 7.0 Hz, 6 H). 6-8 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1 H), 8.30 (dd, J = 7.5, 6.0 Hz, 1 H), 7.68 (d, J = 7.5 Hz, 1 H), 3.08 (p,J = 6.8 Hz, 1 H), 2.76 (t,J = 8.1 Hz, 2 H), 1.47-.33(m, 2 H), 1.26 (d,J = 6.8 Hz, 6 H), 0.89 (t,J = 8.0 Hz, 3 H). 8-4 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.40 (s, 1 H), 7.92 (dd, J = 8.0, 7.0 Hz, 1 H), 7.81 (d, J = 8.0 Hz, 1 H), 3.00 (q, J = 7.5 Hz, 2 H), 1.16 (t, J = 7.5 Hz, 3 H), 1.14 (s, 9 H). 8-8 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1 H),8.24 (dd, J = 7.5, 6.0 Hz, 1 H), 7.65 (d, J = 7.5 Hz, 1 H), 2.76 (t, J = 5.0 Hz, 2 H), 1.47-1.43 (m, 2 H), 1.25 (s, 9H), 0.94 (t, J = 8.0 Hz, 3 H). 10-4 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.40 (s, 1 H), 7.91 (dd, J = 8.0, 7.0 Hz, 1 H), 7.80 (d, J = 8.0 Hz, 1 H), 3.01 (q, J = 7.5 Hz, 2 H), 2.30- 2.20 (m, 1 H), 1.15 (t, J = 7.5 Hz, 3 H), 1.10 - 0.94 (m, 4H) 10-8 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1 H),8.11 (dd, J = 7.5, 6.0 Hz, 1 H), 7.53 (d, J = 7.5 Hz, 1 H), 2.76 (t, J = 7.0 Hz, 2 H), 1.55 - 1.41 (m, 3 H), 0.97 (t, J = 8.0 Hz, 3 H), 0.89 - 0.78 (m, 2 H), 0.71-0.61 (m, 2 H). 12-8 .sup.1H NMR (500 MHz, Chloroform-a) δ 8.19 (s, 1 H), 7.79 (dd, J = 7.5, 6.0 Hz, 1 H), 7.68 (d, J = 7.5 Hz, 1 H), 3.77 (s, 3 H), 2.76 (t, J = 8.0 Hz, 2 H), 1.67-1.58 (m, 2 H), 0.91 (t, J = 8.0 Hz, 3 H). 14-4 .sup.1HNMR (500 MHz, DMSO-d.sub.6) 12.36 (s, 1 H), 7.90 (dd, J = 8.0, 7.0 Hz, 1 H), 7.80 (d, J = 8.0 Hz, 1 H),4.78 (s, 2 H), 3.21 (s, 3 H), 2.97 (q, J = 7.5 Hz, 2 H), 1.14 (t, J = 7.5 Hz, 3 H). 14-8 .sup.1H NMR (500 MHz, Chloroform-a) δ 8.20 (s, 1 H), 7.79 (dd, J = 7.5, 6.0 Hz, 1 H), 7.67 (d, J = 7.5 Hz, 1 H), 4.63 (s, 2 H), 3.35 (s, 3 H), 2.76 (t, J = 5.0 Hz, 2 H), 1.67 (qt, J = 8.0, 5.0 Hz, 2 H), 0.93 (t, J = 8.0 Hz, 3 H). 16-8 .sup.1H NMR (500 MHz, Chloroform-a) δ 8.23 (s, 1 H), 8.19 (dd, J = 7.5, 6.0 Hz, 1 H), 7.42 (d, J = 7.5 Hz, 1 H), 2.76 (t, J = 5.0 Hz, 2 H), 1.67 (qt, J = 8.0, 5.0 Hz, 2 H), 0.95 (t, J = 8.0 Hz, 3 H). 17-4 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.40 (s, 1 H), 7.92 (dd, J = 8.0, 7.0 Hz, 1 H), 7.81 (d, J = 8.0 Hz, 1 H), 3.59 (t, J = 8.5 Hz, 2 H), 3.32 (s, 3 H), 3.00 (q, J = 7.5 Hz, 2 H), 2.77 (t, J = 8.5 Hz, 2 H), 1.16 (t, J = 7.5 Hz, 3 H). 17-5 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.40 (s, 1 H), 8.12 (dd, J = 8.0, 7.0 Hz, 1 H), 8.01 (d, J = 8.0 Hz, 1 H), 3.59 (t, J = 8.5 Hz, 2 H), 3.32 (s, 3 H), 3.20 (q, J = 7.5 Hz, 2 H), 2.77 (t, J = 8.5 Hz, 2 H), 1.23 (t, J = 7.5 Hz, 3 H). 17-8 .sup.1H NMR (500 MHz, Chloroform-a) δ 8.21 (s, 1 H), 7.80 (dd, J = 7.5, 6.0 Hz, 1 H), 7.67 (d, J = 7.5 Hz, 1 H),3.55 (t, J = 8.0 Hz, 2 H), 3.25 (s, 3 H), 2.74-2.65 (m, 4H), 1.67-1.58 (m, 2 H), 0.91 (t, J = 8.0 Hz, 3 H). 18-4 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.59 (s, 1 H), 8.03 (dd, J = 8.0, 7.0 Hz, 1 H), 7.95 (d, J = 8.0 Hz, 1 H), 3.09 (q, J = 7.5 Hz, 2 H), 1.19 (t, J = 7.5 Hz, 3 H) 18-8 .sup.1H NMR (500 MHz, Chloroform-a) δ 8.77 (s, 1 H), 8.32 (dd, J = 7.5, 6.0 Hz, 1 H), 7.68 (d, J = 7.5 Hz, 1 H), 2.76 (t, J = 5.0 Hz, 2 H), 1.67 (qt, J = 8.0, 5.0 Hz, 2 H), 0.97 (t, J = 8.0 Hz, 3 H). 20-2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.53 (s, 1 H), 8.09 (dd, J = 8.0, 7.0 Hz, 1 H), 7.82 (d, J = 8.0 Hz, 1 H), 3.37 (s, 3 H) 20-4 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.51 (s, 1 H), 7.96 (dd, J = 8.0, 7.0 Hz, 1 H), 7.88 (d, J = 8.0 Hz, 1 H), 3.07 (q, J = 7.5 Hz, 2 H), 1.17 (t, J = 7.5 Hz, 3 H) 20-8 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1 H), 8.33 (dd, J = 7.5, 6.0 Hz, 1 H), 7.68 - 7.63 (m, 1 H), 2.76 (t, J = 5.5 Hz, 2 H), 1.47-1.38 (m, 2 H), 0.95 (t, J = 8.0 Hz, 3 H). 21-4 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.41 (s, 1 H), 7.95 (dd, J = 8.0, 7.0 Hz, 1 H), 7.84 (d, J = 8.0 Hz, 1 H), 3.21 -3.17 (m, 1 H), 3.01 (q, J = 7.5 Hz, 2 H), 2.05 - 1.75 (m, 6 H), 1.17 (t, J = 7.5 Hz, 3 H). 21-5 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.41 (s, 1 H), 8.15 (dd, J = 8.0, 7.0 Hz, 1 H), 8.04 (d, J = 8.0 Hz, 1 H), 3.21 -3.17 (m, 1 H), 3.21 (q, J = 7.5 Hz, 2 H), 2.05 - 1.75 (m, 6 H), 1.24 (t, J = 7.5 Hz, 3 H). 21-8 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1 H), 8.11 (dd, J = 7.5, 6.0 Hz, 1 H), 7.53 (dd, J = 7.5, 1.0 Hz, 1 H), 3.24 (p, J = 7.0 Hz, 1 H), 2.76 (t, J = 7.0 Hz, 2 H), 2.38-2.29 (m, 2 H), 2.18 -2.08 (m, 2 H), 2.04 - 1.86 (m, 2 H), 1.47-1.38 (m, 2 H), 0.97 (t, J = 8.0 Hz, 3 H). 22-4 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.43 (s, 1 H), 7.93 (dd, J = 8.0, 7.0 Hz, 1 H), 7.79 (d, J = 8.0 Hz, 1 H), 3.03 (q, J = 7.5 Hz, 2 H), 2.51 (t, J = 7.5 Hz, 2 H), 2.21 -2.10 (m, 2 H), 1.15 (t, J = 7.5 Hz, 3 H) 22-8 .sup.1H NMR (500 MHz, Chloroform-a) δ 8.23 (s, 1 H), 7.80 (dd, J = 7.5, 6.0 Hz, 1 H), 7.68 (d, J = 7.5 Hz, 1 H), 2.76 (t, J = 8.0 Hz, 2 H), 2.53 (t, J = 8.5 Hz, 2 H), 2.14-2.05 (m, 2 H), 1.67-1.55 (m, 2 H), 0.92 (t, J = 8.0 Hz, 3 H). 23-8 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1 H), 8.32 (dd, J = 7.5, 6.0 Hz, 1 H), 7.66 (d, J = 7.5 Hz, 1 H), 3.02 (p, J = 7.0 Hz, 1 H), 2.76 (t, J = 8.0 Hz, 2 H), 1.87- 1.76 (m, 2 H), 1.72- 1.61 (m, 2 H), 1.59 - 1.36 (m, 6 H), 0.90 (t, J = 8.0 Hz, 3 H). 24-4 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.46 (s, 1 H), 7.90 (dd, J = 8.0, 7.0 Hz, 1 H), 7.88 - 7,81 (m, 2 H), 7.78 (d, J = 8.0 Hz, 1 H), 7.27 - 7.19 (m, 3 H), 3.03 (q, J = 7.5 Hz, 2 H), 1.14 (t, J = 7.5 Hz, 3 H) 26-4 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.45 (s, 1 H), 7.90-7.81 (m, 1 H), 7.79-7.72 (m, 1 H), 7.40- 7.24 (m, 5H), 4.26 (s, 2 H) , 3.01 (q, J = 7.5 Hz, 2 H), 1.15 (t, J = 7.5 Hz, 3 H). 29-4 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.73 (s, 1 H), 8.06-7.99 (m, 1 H), 7.94-7.87 (m, 1 H), 7.83- 7.78 (m, 1 H), 7.31-7.26 (m, 1 H), 6.83-6.77 (m, 1 H), 3.00 (q, J = 7.5 Hz, 2 H), 1.16 (t, J = 7.5 Hz, 3 H). 96-4 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.42 (s, 1 H), 7.99 (dd, J = 8.0, 7.0 Hz, 1 H), 7.88 (d, J = 8.0 Hz, 1 H), 6.50 (t, J = 72.5 Hz, 1 H), 3.03 (q, J = 7.5 Hz, 2 H), 1.18 (t, J = 7.5 Hz, 3 H). 96-5 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.42 (s, 1 H), 8.19 (dd, J = 8.0, 7.0 Hz, 1 H), 8.08 (d, J = 8.0 Hz, 1 H), 6.50 (t, J = 72.5 Hz, 1 H), 3.23 (q, J = 7.5 Hz, 2 H), 1.23 (t, J = 7.5 Hz, 3 H). 96-8 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1 H), 7.84 (dd, J = 7.5, 6.0 Hz, 1 H), 7.64 (d, J = 7.5 Hz, 1 H), 6.61 (s, 1 H), 2.76 (t,J = 5.5 Hz, 2 H), 1.47-1.38 (m, 2 H), 0.94 (t, J = 8.0 Hz, 6 H). 101-4 .sup.1HNMR (500 MHz, DMSO-d.sub.6) 12.41 (s, 1 H), 7.94 (dd, J = 8.0, 7.0 Hz, 1 H), 7.86 (d, J = 8.0 Hz, 1 H), 6.71-6.60 (m, 1 H), 5.81-5.72 (m, 1 H), 5.53-5.45 (m, 1 H), 3.02 (q, J - 7.5 hz, 2 H), 1.17 (t, J = 7.5 Hz, 3 H). 101-5 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.41 (s, 1 H), 8.14 (dd, J = 8.0, 7.0 Hz, 1 H), 8.06 (d, J = 8.0 Hz, 1 H), 6.71-6.60 (m, 1 H), 5.81-5.72 (m, 1 H), 5.53-5.45 (m, 1 H), 3.22 (q, J - 7.5 hz, 2 H), 1.23 (t, J = 7.5 Hz, 3 H). 101-8 .sup.1HNMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1 H), 7.84 (dd, J = 7.5, 6.0 Hz, 1 H), 7.64 (d, J = 7.5 Hz, 1 H), 6.37 (dd, J = 16.5, 10.0 Hz, 1 H), 5.73 (dd, J = 14.0, 10.0 Hz, 1 H), 5.48 (dd, J = 16.5, 14.0 Hz, 1 H), 2.76 (t, J = 5.5 Hz, 2 H), 1.47-1.38 (m, 2 H), 0.94 (t, J = 8.0 Hz, 3 H). 103-4 .sup.1HNMR (500 MHz, DMSO-d.sub.6) 12.41 (s, 1 H), 7.94 (dd, J = 8.0, 7.0 Hz, 1 H), 7.86 (d, J = 8.0 Hz, 1 H), 4.13 (s, 1 H), 3.02 (q, J = 7.5 Hz, 2 H), 1.17 (t, J = 7.5 Hz, 3 H). 103-5 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.41 (s, 1 H), 8.14 (dd, J = 8.0, 7.0 Hz, 1 H), 8.05 (d, J = 8.0 Hz, 1 H), 4.13 (s, 1 H), 3.22 (q, J = 7.5 Hz, 2 H), 1.22 (t, J = 7.5 Hz, 3 H). 103-8 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1 H), 7.82 (dd, J = 7.5, 6.0 Hz, 1 H), 7.66 (dd, J = 7.5, 1.0 Hz, 1 H), 4.28 (s, 1 H), 2.76 (t, J = 5.5 Hz, 2 H), 1.47-1.42 (m, 2 H), 0.94 (t,J = 8.0 Hz, 3 H). 148-8 .sup.1HNMR (500 MHz, DMSO-d.sub.6) δ 12.38 (s, 1 H), 8.11 (dd, J = 7.5, 6.0 Hz, 1 H), 7.53 (d, J+327.5, 1.0 Hz, 1 H), 2.76 (t, J = 7.0 Hz, 2 H), 1.56 ? 1.41 (m, 4H), 0.97 (t, J = 8.0 Hz, 3 H), 0.87 (d, J = 6.6 Hz, 3 H), 0.63-0.54 (m, 1 H), 0.38-0.29 (m, 1 H). 149-8 .sup.1HNMR (500 MHz, Chloroform-a) δ 8.23 (s, 1 H),8.08 (dd, J = 7.5, 6.0 Hz, 1 H), 7.52 (d, J = 7.5 Hz, 1 H), 6.60 (q, J = 7.0 Hz, 1 H), 6.50 (q, J = 7.0 Hz, 1 H), 2.76 (t, J = 7.0 Hz, 2 H), 2.05-1.91 (m, 1 H), 1.73 ? 1.61 (m, 1 H), 1.08-0.92 (m, 1 H), 0.95 (t, J = 8.0 Hz, 3 H), 0.82-0.73 (m, 1 H). 150-8 .sup.1HNMR (500 MHz, Chloroform-a) δ 8.23 (s, 1 H),8.08 (dd, J = 7.5, 6.0 Hz, 1 H), 7.52 (d, J = 7.5 Hz, 1 H), 2.76 (t, J = 7.0 Hz, 2 H), 2.60 -2.51(m, 1 H), 1.73 ? 1.61 (m, 2 H), 1.51-1.40 (m, 1 H), 1.26- 1.13 (m, 1 H), 0.95 (t, J = 8.0 Hz, 3 H). 151-8 .sup.1HNMR (500 MHz, Chloroform-a) δ 8.23 (s, 1 H), 8.08 (dd, J = 7.5, 6.0 Hz, 1 H), 7.52 (d,J = 7.5 Hz, 1 H), 7.37-7.32 (m, 2 H), 7.25-7.14 (m, 3 H), 3.51 (t, J = 7.0 Hz, 1 H), 2.76 (t, J = 7.0 Hz, 2 H), 2.45 (q, J = 7.0 Hz, 1 H), 1.73 ? 1.61 (m, 2 H), 1.50-1.41 (m, 1 H), 1.25-1.16 (m, 1 H), 0.95 (t, J = 8.0 Hz, 3 H). 152-4 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.60 (s, 1 H), 8.18-7.95 (m, 3 H), 7.52-7.35 (m, 2 H), 3.02 (q, J = 7.5 Hz, 2 H), 1.19 (t, J = 7.5 Hz, 3 H).

[0164] 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.

[0165] 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.

[0166] Examples of representative compounds are as follows:

[0167] 1. Synthesis of Compound 1-4

##STR00856##

[0168] (1) Compound II (3 g, 16 mmol, 1.0 eq), NaOH (0.72 g, 18 mmol, 1.1 eq) were added sequentially into 30 ml of DMF, and then compound a (1.07 g, 1.2 mmol, 1.05 eq) was added dropwise at 0° C., and the reaction solution was stirred at 0° C. for 1 hour. When LCMS test showed that the reaction of starting materials was basically completed, there was one major new peak. The reaction solution was poured into 30 ml of water, and the mixture was separated, and the aqueous phase was extracted once with 50 ml of ethyl acetate, and the resultant organic phase was washed three times with saturated saline solution (50 ml), dried, evaporated to dryness under reduced pressure and separated by column chromatography to obtain compound b (3.4 g, 92% yield) (colorless oil).

##STR00857##

[0169] (2) Compound b (3 g, 13 mmol, 1.0 eq) was added to 30 ml of THF, then n-BuLi (6.42 ml, 2.5 M, 16 mmol, 1.2 eq) was slowly added at −78° C., then the reaction solution was stirred at −78° C. for 0.5 hour, and slowly fed with CO.sub.2 for 10 minutes, then the reaction solution was slowly warmed to room temperature. The product was detected by LCMS. 20 ml of water was poured into the reaction solution, the mixture was separated, the aqueous phase was extracted once with 30 ml of ethyl acetate, and the resultant aqueous phase was gradually adjusted to pH=4-5 with concentrated hydrochloric acid, filtered and dried to give compound c (3 g, 83.6% yield) (white solid).

##STR00858##

[0170] (3) Compound c (3 g, 11 mmol, 1.0 eq), compound d (1.66 g, 16.8 mmol, 1.5 eq), DMAP (0.13 g, 1.1 mmol, 0.1 eq) were sequentially added to 30 ml of pyridine. Then, SOCl.sub.2 (2.0 g, 16.8 mmol, 1.5 eq) was slowly added at 0° C., and the reaction solution was stirred at room temperature for 3 hours. The product was detected by LCMS. Pyridine was removed by concentration, then 30 ml of water was poured into the reaction solution, and the mixture was separated. The aqueous phase was extracted three times with 30 ml of ethyl acetate, and the resultant organic phase was washed three times with saturated saline solution (50 ml), dried, and evaporated to dryness under reduced pressure and separated by column chromatography to to obtain Compound 1-4 (2.5 g, 64% yield) (white solid).

[0171] 2. Synthesis of Compound 1-5

##STR00859##

[0172] Compound 1-4 (1 g, 2.8 mmol, 1.0 eq) and compound e (0.54 g, 3.1 mmol, 1.1 eq) were added sequentially in 10 mL of dichloromethane. The reaction solution was then stirred at room temperature for 1 hour. The product was detected by LCMS, and the reaction of raw materials was basically completed. The reaction solution was poured into 10 ml of water, the reaction was quenched with sodium hydrogen sulfite, and the mixture was separated. The aqueous phase was extracted three times with 30 ml of dichloromethane, and the resultant organic phase was washed once with saturated saline solution (30 ml), dried, and evaporated to dryness under reduced pressure, and separated by column chromatography to give Compound 1-5 (0.8 g, 76.5% yield) (greyish white solid).

[0173] 3. Synthesis of Compound 1-6

##STR00860##

[0174] Compound 1-4 (1 g, 2.8 mmol, 1.0 eq) and compound e (1.24 g, 7.2 mmol, 2.5 eq) were added sequentially in 10 mL of dichloromethane. The reaction solution was then stirred at room temperature for 24 hours. The product was detected by LCMS and the reaction of raw materials was basically completed. The reaction solution was filtrated, the filtrate was quenched with sodium hydrogen sulfite, concentrated and separated by column chromatography to give Compound 1-6 (0.5 g, 45.8% yield) (greyish white solid).

[0175] 4. Synthesis of Compound 1-69

##STR00861##

[0176] (1) Compound 1-136 was prepared by using the above method for synthesis of Compound 1-4, and then Compound 1-136 (0.34 g, 1.0 mmol, 1.0 eq) was added to 5 ml of TFA, and then the reaction solution was stirred at 90° C. for 16 hours. The product was detected by LCMS, and evaporated to dryness under reduced pressure to give compound A (0.29 g) (yellow oil, crude).

##STR00862##

[0177] (2) Compound A (0.32 g, 1.0 mmol, 1.0 eq), K.sub.2CO.sub.3 (0.28 g, 2 mmol, 2.0 eq) and compound B (0.13 g, 1.1 mmol, 1.1 eq) were sequentially added in 10 ml of DMF, then the reaction solution was stirred at 25° C. for 2 hours. The product was detected by LCMS. The reaction solution was poured into 20 ml of water, and the mixture was separated, the aqueous phase was extracted three times with 20 ml of ethyl acetate, and the resultant organic phase was washed three times with saturated saline solution (20 ml), dried, and evaporated to dryness under reduced pressure, and separated by column chromatography to give Compound 1-69 (0.25 g, 69% yield) (white solid).

[0178] 5. Synthesis of Compound 1-112

##STR00863##

[0179] Compound 1-4 (500 mg, 1.4 mmol), Compound C (367 mg, 2.1 mmol), potassium carbonate (595 mg, 2.8 mmol) and acetonitrile 10 mL were placed in a round bottom flask, and stirred at 80° C. for 12 hours. The completion of the reaction was detected by high performance liquid chromatography, then the temperature of the reaction solution was lowered to 20° C., and the remaining potassium carbonate solid was filtered off, and the mother liquid was directly separated by prep-HPLC to obtain Compound 1-112 (160 mg, 25% yield, white solid).

[0180] 6. Synthesis of Compound 1-118

##STR00864##

[0181] Compound 1-4 (500 mg, 1.4 mmol), a catalytic amount of 4-dimethylaminopyridine (10 mg) and 5 mL of pyridine were placed in a round bottom flask, heated to 60° C., and Compound D (1.1 g, 7.0 mmol) was slowly added dropwise under the protection of nitrogen atmosphere. The completion of the reaction was detected by high performance liquid chromatography, the temperature of the reaction solution was lowered to 20° C., and the reaction system was concentrated and separated by prep-HPLC to give Compound 1-118 (150 mg, 22% yield, yellow solid).

[0182] 7. Synthesis of Compound 1-127

##STR00865##

[0183] (1) Compound II (3 g, 16 mmol, 1.0 eq), NaOH (0.72 g, 18 mmol, 1.1 eq) were sequentially added to 30 ml of DMF, then compound f (0.8 g, 17 mmol, 1.05 eq) was added dropwise at 0° C., then the reaction solution was stirred at 0° C. for 1 hour. When LCMS detection showed the reaction of starting materials were basically completed, there was one major new peak. The reaction solution was poured into 30 ml of water, and the mixture was separated, and the aqueous phase was extracted once with 50 ml of ethyl acetate, and the resultant organic phase was washed three times with saturated saline solution (50 ml), dried, evaporated to dryness under reduced pressure, and separated by column chromatography to give compound g (3.0 g, 90% yield) (colorless oil).

##STR00866##

[0184] (2) Compound g (2.8 g, 13 mmol, 1.0 eq) was added to 30 ml of THF, then n-BuLi (6.42 ml, 2.5 M, 16 mmol, 1.2 eq) was slowly added at −78° C., then the reaction solution was stirred at −78° C. for 0.5 hour, and then slowly fed with CO.sub.2 for 10 minutes, the reaction solution was slowly warmed to room temperature. The product was detected by LCMS. 20 ml of water was poured into the reaction solution, and the mixture was separated. The aqueous phase was extracted once with 30 ml of ethyl acetate, and the resultant aqueous phase was gradually adjusted to pH=4 to 5 with concentrated hydrochloric acid, filtered and dried to give compound h (2.7 g, 85% yield) (white solid).

##STR00867##

[0185] (3) Compound h (2.7 g, 11 mmol, 1.0 eq), compound d (1.66 g, 16.8 mmol, 1.5 eq), DMAP (0.13 g, 1.1 mmol, 0.1 eq) were added sequentially to 30 ml of pyridine. Then, SOCl.sub.2 (2.0 g, 16.8 mmol, 1.5 eq) was slowly added at 0° C., and then the reaction solution was stirred at room temperature for 3 hours. The product was detected by LCMS. Pyridine was removed by concentration, then 30 ml of water was poured into the reaction solution, and the mixture was separated. The aqueous phase was extracted three times with 30 ml of ethyl acetate, and the resultant organic phase was washed three times with saturated saline solution (50 ml), dried, and evaporated to dryness under reduced pressure, and separated by column chromatography to give Compound 1-127 (2.3 g, 63% yield) (white solid).

[0186] 8. Synthesis of Compound 1-132

##STR00868##

[0187] (1) Compound II (3 g, 16 mmol, 1.0 eq), NaOH (0.72 g, 18 mmol, 1.1 eq) were added to 30 ml of DMF, then compound i (17 ml, 1M in THE, 17 mmol, 1.05 eq) was added dropwise at 0° C., then the reaction solution was stirred at 0° C. for 1 hour. When LCMS detection showed that the reaction of starting materials was basically completed, there was one major new peak. The reaction solution was poured into 30 ml of water, and the mixture was separated. The aqueous phase was extracted once with 50 ml of ethyl acetate, and the resultant organic phase was washed three times with saturated saline solution (50 ml), dried, evaporated to dryness under reduced pressure, and separated by column chromatography to give compound j (3.1 g, 92% yield) (colorless oil).

##STR00869##

[0188] (2) Compound j (2.75 g, 13 mmol, 1.0 eq) was added to 30 ml of THF, then n-BuLi (6.42 ml, 2.5 M, 16 mmol, 1.2 eq) was slowly added at −78° C., then the reaction solution was stirred at −78° C. for 0.5 hour, and then slowly fed with CO.sub.2 for 10 minutes, the reaction solution was slowly warmed to room temperature. The product was detected by LCMS. 20 ml of water was poured into the reaction solution, the mixture was separated. The aqueous phase was extracted once with 30 ml of ethyl acetate, and the resultant aqueous phase was gradually adjusted with concentrated hydrochloric acid to pH=4 to 5, filtered and dried to obtain compound k (2.5 g, 80% yield) (white solid).

##STR00870##

[0189] (3) Compound k (2.5 g, 11 mmol, 1.0 eq), compound d (1.66 g, 16.8 mmol, 1.5 eq), DMAP (0.13 g, 1.1 mmol, 0.1 eq) were sequentially added to 30 ml of pyridine. Then, SOCl.sub.2 (2.0 g, 16.8 mmol, 1.5 eq) was slowly added at 0° C., and then the reaction solution was stirred at room temperature for 3 hours. The product was detected by LCMS. Pyridine was removed by concentration, then 30 ml of water was poured into the reaction solution, and the mixture was separated. The aqueous phase was extracted three times with 30 ml of ethyl acetate, and the resultant organic phase was washed three times with saturated saline solution (50 ml), dried, evaporated to dryness under reduced pressure, and separated by column chromatography to give Compound 1-132 (2.1 g, 61% yield) was obtained (white solid).

[0190] 9. Synthesis of Compound 1-8 (R-Configuration)

[0191] Compound 1-8 was prepared according to the method for the preparation of the above Compound 1-5, and then Compound 1-8 (0.5 g, 98% purity) was passed through chiral HPLC (Column: CHIRALPAK IG; Column Size: 3 cm×25 cm, 5 um; Injection: 3.0 ml; Mobile phase: Hex (0.2% FA): IPA=50:50; Flow rate: 28 ml/min; Wavelength: UV 254 nm; Temperature: 25° C.; Sample solution: 70 mg/ml in EtOH/DCM; Run time=60 minutes) for separation, and then concentrated to obtain Compound 1-8 (R-configuration) (0.16 g, Rt=10.51 min, 100% ee, purity 98%) and Compound 1-8 (S-configuration) (0.13 g, Rt=30.81 min, 99.8% ee, purity 96%) in white solids, which were confirmed by single crystal diffraction.

##STR00871##

[0192] Biological Activity Evaluation:

[0193] The activity level criteria for plant damage (i.e., growth control rate) are as follows:

[0194] Level 5: growth control rate is above 85%;

[0195] Level 4: growth control rate is greater than or equal to 60% and less than 85%;

[0196] Level 3: growth control rate is greater than or equal to 40% and less than 60%;

[0197] Level 2: growth control rate is greater than or equal to 20% and less than 40%;

[0198] Level 1: growth control rate is greater than or equal to 5% and less than 20%;

[0199] Level 0: growth control rate is less than 5%.

[0200] The above growth control rates are fresh weight control rates.

[0201] Experiment on weeding effect in post-emergence stage: monocotyledonous and dicotyledonous weed seeds (Descurainia sophia, Capsella bursa-pastoris, Abutilon theophrasti, Galium aparine, Stellaria media, Lithospermum arvense, rorippa indica, Alopecurus aequalis, Beckmannia syzigachne, Sclerochloa dura, Phleum paniculatum, Bromus japonicus, Aegilops tauschii, Phalaris arundinacea, Amaranthus retroflexus, Chenopodiaceae, 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 to 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-00004 TABLE 2 Results on weeding effect in post-emergence stage Compound Echinochloa Digitaria Abutilion Amaranthus Stellaria Dose (g No. crusgah sanguinalis theophrasti retroflexus media a.i./ha) 1-1  4 4 4 4 4 500 1-1  4 3 4 4 4 250 1-1  4 2 4 4 4 125 1-1  2 1 2 4 3  60 1-2  4 4 4 4 4 500 1-2  4 4 4 4 4 250 1-2  4 3 4 4 3 125 1-2  3 3 4 4 3  60 1-4  5 5 5 5 5 250 1-4  5 5 5 5 5 125 1-5  5 5 5 5 5 125 1-5  5 5 5 5 5  60 1-6  5 5 5 5 5 250 1-6  5 5 5 5 5 125 1-7  5 5 5 5 5 500 1-7  5 5 5 5 5 250 1-8  5 5 5 5 5 125 1-8  5 5 5 5 5  60 1-9  5 5 5 5 5 250 1-9  5 5 5 5 5 125 1-10  5 N 5 5 5 250 1-11  5 5 5 5 5 250 1-12  5 5 5 5 5 250 1-13  5 5 5 5 5 250 1-14  5 5 5 5 5 125 1-15  N N 5 5 5 250 1-20  5 5 5 5 5 250 1-29  5 5 5 5 5 500 1-40  5 5 N 5 N 500 1-43  5 N N N N 500 1-48  5 5 N N N 500 1-49  5 5 5 5 5 500 1-50  5 5 5 5 5 500 1-51  5 5 5 5 5 500 1-52  5 5 5 5 5 500 1-53  5 5 5 5 5 500 1-54  5 5 N N N 500 1-57  5 5 5 5 5 500 1-59  5 5 5 5 5 500 1-68  5 N N N N 500 1-69  5 N N N N 500 1-70  5 N N N N 500 1-82  5 5 5 5 5 500 1-137 5 5 5 5 5 500 1-138 5 5 N N N 500 1-143 5 N 5 5 5 500 1-144 5 N 5 5 5 500 1-392 5 5 5 5 5 500 1-394 5 N N N N 500 1-395 5 5 5 5 N 500 1-397 5 5 5 5 5 500 1-398 5 5 5 5 5 500 1-401 5 5 5 5 N 250 1-402 5 5 5 5 N 250 1-403 5 5 5 5 N 125 1-404 5 5 5 5 N 125 1-411 5 5 5 5 N 250 1-412 5 5 5 5 N 250 1-413 5 5 N 5 N 500 1-414 5 5 5 5 N 250 1-427 5 5 5 5 N 500 1-428 5 5 5 5 N 500 1-429 5 5 5 N N 500 1-430 5 5 5 N N 500 1-441 5 5 5 5 5 500 1-443 5 5 5 5 5 500 1-444 5 N N N N 500 1-446 5 5 5 5 5 250 1-447 5 5 5 5 5 500 1-448 5 5 5 5 5 500 1-452 5 5 5 5 5 250 1-457 5 5 N N N 500 1-525 5 N N N N 500 1-537 5 N N N N 500 1-541 5 N 5 5 N 500 1-543 5 5 5 5 5 500 1-552 5 5 5 N 5 250 1-558 5 N N N N 500 1-560 5 N 5 N N 500 1-563 5 5 5 5 5 500 1-566 5 N N N N 500 1-617 5 5 N N N 500 2-4  5 5 5 5 5 500 3-4  5 5 5 5 5 500 3-5  5 5 5 5 5 500 3-8  5 5 5 5 5 500 3-11  5 5 5 5 5 500 3-14  5 5 5 5 5 500 3-17  5 5 5 5 5 500 3-20  5 N N N N 500 3-52  5 5 5 5 5 500 3-54  5 5 5 5 5 500 3-57  5 5 5 5 5 500 Control 0 1 N 1 0 500 Compound A Note: Control compound A: [00872]N indicates partial data were unavailable.

TABLE-US-00005 TABLE 3 Results on weeding effect in post-emergence stage Echinochloa Abutilon Digitaria Compound No. crusgali theophrasti sanguinahs Setaria viridis Dose (g a.i./ha) 1-1 N 4 2 2 120 1-1 2 2 1 1 60 1-1 2 N 1 1 30 1-1 1 N 0 0 15 1-1 0 N 0 0 7.5 1-2 (R- 4 N 4 3 60 configuration) 1-2 (R- 3 N 3 3 30 configuration) 1-2 (R- 1 N 1 2 15 configuration) 1-2 (R- 0 N 0 0 7.5 configuration) 1-2 3 4 3 3 60 1-4 N 5 5 5 60 1-5 (R- 5 N 5 5 60 configuration) 1-5 (R- 5 N 5 5 30 configuration) 1-5 (R- 5 N 5 5 15 configuration) 1-5 (R- 5 N 4 4 7.5 configuration) 1-5 (R- 4 N 3 3 3.75 configuration) 1-5 5 5 5 5 60 1-8 (R- 5 N 5 5 60 configuration) 1-8 (R- 5 N 5 5 30 configuration) 1-8 (R- 5 N 5 5 15 configuration) 1-8 (R- 5 N 5 4 7.5 configuration) 1-8 (R- 5 N 4 2 3.75 configuration) 1-8 5 5 5 5 60 1-14 (R-configuration) 5 N 5 5 60 1-14 (R-configuration) 5 N 5 5 30 1-14 (R-configuration) 5 N 5 4 15 1-14 (R-configuration) 5 N 4 4 7.5 1-14 N 5 5 5 60 1-17 N 5 5 5 60 1-20 N 5 5 5 60 1-52 N 5 5 5 60 1-57 (R-configuration) 5 N 5 5 125 1-82 (R-configuration) 5 N 5 5 125 1-392 (R-configuration) 5 N 5 5 500 1-395 (R-configuration) 5 N 5 5 500 1-397 (R-configuration) 5 N 5 5 125 1-398 (R-configuration) 5 N 5 5 250 1-401 (R-configuration) 5 N 5 5 500 1-402 (R-configuration) 5 N 5 5 500 1-403 (R-configuration) 5 N 5 5 60 1-404 (R-configuration) 5 N 5 5 60 1-405 (R-configuration) 5 N 5 5 125 1-411 (R-configuration) 5 N 5 5 250 1-412 (R-configuration) 5 N 5 5 500 1-413 (R-configuration) 5 N 5 5 500 1-414 (R-configuration) 5 N 5 5 500 1-427 (R-configuration) 5 N 5 5 500 1-428 (R-configuration) 5 N 5 5 500 1-429 (R-configuration) 5 N 5 5 500 1-430 (R-configuration) 5 N 5 5 500 1-431 (R-configuration) 5 N 5 5 500 1-432 (R-configuration) 5 N 5 5 500 1-441 (R-configuration) 5 N 5 5 500 1-443 (R-configuration) 5 N 5 5 500 1-444 (R-configuration) 5 N 5 5 500 1-446 (R-configuration) 5 N 5 5 500 1-447 (R-configuration) 5 N 5 5 500 1-448 (R-configuration) 5 N 5 5 500 1-523 (R-configuration) 5 N 5 5 500 1-525 (R-configuration) 5 N 5 5 500 1-552 (R-configuration) 5 N 5 5 125 1-563 (R-configuration) 5 N N N 125 1-617 (R-configuration) 5 N 5 5 60 2-8 (R- 5 N 5 5 250 configuration) 3-4 5 N 5 5 250 3-5 (R- 5 N 5 5 120 configuration) 3-8 (R- 5 N 5 5 60 configuration) 3-11 (R-configuration) 5 N 5 5 125 3-14 (R-configuration) 5 N 5 5 60 3-17 (R-configuration) 5 N 5 5 125 3-20 (R-configuration) 5 N 5 5 125 3-52 (R-configuration) 5 N 5 5 125 3-54 5 N 5 5 250 3-57 (R-configuration) 5 N 5 5 125 6-8 (R- 5 N 5 5 250 configuration) Control N 3 1 1 120 Compound A

[0202] It was found that when the group Y in the compound of the formula of the present invention was changed from methyl to ethyl or C.sub.3-C.sub.8 alkyl, the herbicidal activity and herbicidal spectrum thereof were significally improved. Especially at low doses, the activity on the gramineous weed (such as the main gramineous weed Echinochloa crusgali, Leptochloa chinensis or Digitaria sanguinalis) of Compound 1-4 was higher by more than 2 times than Compound 1-1, the activity of Compound 1-5 was higher by more than 2 times than and Compound 1-2, Compound 1-8 was much more higher than Compound 1-2; when the carbon number exceeded 8, the activity was significantly decreased; while the change of carbon atom number in other groups in the formula had no significant effect on the activity.

[0203] Comparative Experiments:

TABLE-US-00006 TABLE 4 Safety test results of control experiments (the herbicide selection index between rice and Echinochloa crusgali was calculated by dividing the average dose of causing 10% phytotoxicity to rice by the average dose of causing 90% control efficiency to Echinochloa crusgali, which was an important index for safety evaluation of rice field herbicides. When a herbicide had a selection index of less than 2, its risk was relatively higher and it had no commercial value.) Selection index Indica rice Japonica rice between rice and Compound No. (Huanghuazhan) (Huaidao No. 5) Dose Echinochloa crusgali 1-5   0 0 250 g a.i./ha >5 1-6   0 0 250 g a.i./ha >5 1-7   0 0 250 g a.i./ha >5 1-8   0 0 250 g a.i./ha >5 1-9   0 0 250 g a.i./ha >5 1-13  0 0 250 g a.i./ha >5 1-14  0 0 250 g a.i./ha >5 1-20  0 0 250 g a.i./ha >5 1-52  0 0 250 g a.i./ha >5 1-57  0 0 250 g a.i./ha >5 1-82  0 0 250 g a.i./ha >5 1-134 0 0 250 g a.i./ha >5 Control 4 3 250 g a.i./ha 0.8 Compound B Control 3 3 125 g a.i./ha 0.8 Compound B Control 5 4 125 g a.i./ha 1.1 Compound C Control 5 5  60 g a.i./ha 1 Compound D Note: Control Compound B: [00873]Control Compound C: [00874]Control compound D: [00875]

[0204] From Table 4, it was understood that the compounds of the present invention had very high safety and selectivity for rice, while the control compounds were unsafe for rice, which produced unacceptable phytotoxicity for both indica rice and japonica rice.

[0205] In summary, the compounds of the present invention were very safe to rice, and their selection indexes were much greater than 2, and could effectively prevent gramineous weeds such as Echinochloa crusgali, Digitaria sanguinalis, Setaria viridis, and various broad-leaved weeds, and thus were ideal herbicides for rice fields.

[0206] Experiment on weeding effect in post-emergence stage: after 3-4 weeks of sowing, the test plants were treated in the 1.5-2 leaf stage of the directly sowed rice Longyang 16, and the 4-5 leaf stage of weeds. After the application of the compounds of the present invention, the plants were cultured for 25 days in the greenhouse, and then the experimental results of the weeding were counted. The test results were shown in Tables 5-6.

TABLE-US-00007 TABLE 5 Control experiment results of R configuration compound activity (inhibition rate, %) Digitaria Leptochloa Ablation sanguinalis (30 g Green Setaria chinensis theophrasti (30 Compound No. a.i./ha) viridis (60 g a.i./ha) (60 g a.i./ha) g a.i./ha) 1-8 (R-configuration) 100% 100% 85% 100% 1-8 (S-configuration)  0%  15%  0%   0% 1-8  80%  90% 30%  90% 1-2  0%  20%  0%  60%

TABLE-US-00008 TABLE 6 Control experiment results of R configuration compound activity (inhibition rate, %) Green Leptochloa Setaria chinensis Rice Rice viridis (30 (125 (Longyang 16) (Longyang 16) Compound No. g a.i./ha) g a.i./ha) (250 g a.i./ha) (500 g a.i./ha) 1-8 (R- 75% 100%  0%  0% configuration) 1-8 (S-  0%  10% 15% 25% configuration) 1-8 10%  80%  5% 15%

[0207] Longyang 16 is a representative and important long-grain fragrant rice in Northeast China. Long-grain fragrant rice is more sensitive to herbicides, especially to HPPD herbicides such as Mesotrione, Benzobicylon and the like, which are prone to causing phytotoxicity. Unexpectedly, compound 1-8 (R-configuration) had high safety on rice (Longyang 16) and had better activity against key weed Leptochloa chinensis, while the S-configuration was not safe for rice, i.e., had severe phytotoxicity on crops, and had lower activity on key weeds, even had no activity at low dose. It was inconsistent with our well-known structure-activity relationships about aryloxyphenoxypropionic acid herbicides and phenoxypropionic acid herbicides that their active isomers had high activity and heavy phytotoxicity while their inactive isomers had almost no activity.

[0208] Experiment on weed effect in pre-emergence stage:

[0209] Seeds of monocotyledonous and dicotyledonous weeds and main crops (e.g. 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. The test results were observed 4 weeks later. 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 crusgali, Digitaria sanguinalis and Abutilon theophrasti, etc. And many compounds had good selectivity for corn, wheat, rice, soybean, oilseed rape, etc.

[0210] It is indicated from the experiment that the compound of the present invention generally have good weed control efficacy, especially for major grass weeds such as echinochloa crusgali, Digitaria sanguinalis and Setaria viridis, etc. and major broad-leaved weeds such as Abutilon theophrasti, rorippa indica and Bidens pilosa, which are widely occurred in corn, rice and wheat fields, and have excellent commercial value. Above all, it is noted that the compound of the invention have extremely high activity to broad-leaved weeds, which are resistant to ALS inhibitor, like rorippa indica, Descurainia sophia, Capsella bursa-pastoris, Lithospermum arvense, Galium aparine and Stellaria media, etc.

[0211] Transplanted rice safety evaluation and weed control effect evaluation in rice field:

[0212] Rice field soil was loaded into a 1/1,000,000 ha pot. The seeds of echinochloa crusgali, scirpus juncoides, Bidens tripartita, Sagittaria trifolia, Monochoria vaginalis and Leptochloa chinensis 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 crusgali, scirpus juncoides, Bidens tripartita, Monochoria vaginalis and Leptochloa chinensis reached 0.5 leaf stage and Sagittaria trifolia reached the time point of primary leaf stage.

[0213] 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/Indica 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.

[0214] The fertility condition of echinochloa crusgali, scirpus juncoides, Bidens tripartita, Leptochloa chinensis, Sagittaria trifolia and Monochoria vaginalis 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 0-5 activity standard level. Many compounds show excellent activity and selectivity.

TABLE-US-00009 TABLE 7 Experimental results of activity and safety (dose: 125 g a.i./ha) Echinochloa Monochoria Compound No. crusgali Scirpus juncoides vaginalis Rice 1-4 5 5 5 0 1-5 5 5 5 0 1-6 5 5 5 0 1-8 5 5 5 0 1-11 5 5 5 0 1-14 5 5 5 0 1-57 5 5 5 0 1-76 5 5 5 0

TABLE-US-00010 TABLE 8 Herbicidal effects of compounds (the dose of the compounds of the present invention: 60 g a.i./ha) Echinochloa Leptochloa Sagittaria Monochoria Compound No. crusgali chinensis trifolia vaginalis Rice 1-8 (R-configuration) 5 5 5 5 0 1-14 (R-configuration) 5 5 5 5 0 1-20 (R-configuration) 5 5 5 5 0 1-82 (R-configuration) 5 5 5 5 0 1-403 (R-configuration) 5 5 5 5 0 1-414 (R-configuration) 5 5 5 5 0 Penoxsulam (30 g a.i./ha) 0 1 0 1 1 Note: The seeds of Echinochloa crusgali, Scirpus juncoides, Bidens tripartita, Sagittaria trifolia and Monochoria vaginalis were collected from Heilongjiang Province of China. The tests indicated that the weeds were resistant to the common doses of Pyrazosulfuron-ethyland Penoxsulam.

[0215] It could be seen from the present experiment that the compound of the present invention had excellent activity against weeds having an anti-ALS inhibiting mechanism and being a serious challenge in production, and thus could solve the increasingly serious resistance problem.

[0216] In addition, the present invention further relates to a herbicidal composition comprising herbicidally effective amounts of active ingredient (i) (such as the compound represented by Formula I) and active ingredient (ii), wherein the herbicidal composition may further comprise one or more safeners and/or agrochemically acceptable formulation auxiliaries, and the like.

[0217] Wherein, the actual weed control effects of the mixtures of the above active ingredients (i) and (ii) were determined by stem-leaf treatment method, i.e., the weeds in the 3-4 leaf stage were sprayed evenly on stems and leaves by a hand sprayer, in which the added-water amount was 30 kg/667 m.sup.2. The investigation was carried out after 20 days of treatment, and the theoretical fresh weight inhibition rate (calculation formula: E0=X+Y−X*Y/100) of each mixture in the treatment was calculated by Gowing method, and then compared with the measured inhibition rate (E), and the type of combined effect on weeds for the two ingredients in the mixture was evaluated, in which if E-E0 value is greater than 10%, the type of combined effect was synergism; if E-E0 value is less than −10%, the type of combined effect was antagonism; if E-E0 value is between −10% and 10%, the type of combined effect was additive effect. According to the actual control effect and the property of the herbicides, the balance of the formula and other factors, the optimal ratio was determined. In the calculation formula: X represents the fresh weight inhibition rate when the active ingredient (i) is used in an amount of P; and Y represents the fresh weight inhibition rate when the active ingredient (ii) is used in an amount of Q. The statistical results are shown in Tables 9-11 below.

TABLE-US-00011 TABLE 9 Evaluation of actual control effects and combined effects of the mixtures of active ingredients (i) and (ii) in weeds (Gowing method) Active Control effect Control effect Ingredient Active (i) + (ii) of (i) alone of (ii) alone (i)/Comp. Ingredient g at corresponding at corresponding E E0 E − E0 No. (ii) a.i./mu Weed type dose (%) dose (%) (%) (%) (%) 1-1 Florpyrauxifen- .sup. 3 + 0.6 Echinochloa 43.1 21.5 78.1 55.33 22.77 benzyl phyllopogon 1-1 Florpyrauxifen- 1 + 3 Echinochloa 8.3 70.5 87.9 72.95 14.95 benzyl phyllopogon 1-1 Fluroxypyr 15 + 3  Monochoria 23.9 60.3 83.2 69.79 13.41 vaginalis 1-1 Fluroxypyr 5 + 5 Monochoria 9.6 73.4 90.5 75.95 14.55 vaginalis 1-1 MCPA 15 + 3  Monochoria 23.9 28.2 62.1 45.36 16.74 vaginalis 1-1 MCPA 5 + 3 Monochoria 9.6 28.2 51.2 35.09 16.11 vaginalis 1-1 2,4-D butyric 15 + 3  Monochoria 23.9 23.5 56.7 41.78 14.92 acid vaginalis 1-1 2,4-D butyric  5 + 15 Monochoria 9.6 65.3 80.8 68.63 12.17 acid vaginalis 1-1 Dicamba 5 + 3 Monochoria 9.6 50.9 70.5 55.61 14.89 vaginalis 1-1 Dicamba 5 + 5 Monochoria 9.6 70.2 86.2 73.06 13.14 vaginalis 1-1 Quinclorac 2 + 3 Echinochloa 18.7 35.2 62.5 47.32 15.18 phyllopogon 1-1 Quinclorac  3 + 15 Echinochloa 43.1 52.9 92.2 73.20 19.00 phyllopogon 1-1 Quintrione 1 + 3 Echinochloa 8.3 15.8 45.5 22.79 22.71 phyllopogon 1-1 Quintrione  3 + 30 Echinochloa 43.1 66.7 94.6 81.05 13.55 phyllopogon 1-1 Clopyralid 5 + 1 Monochoria 9.6 49.6 77.3 54.44 22.86 vaginalis 1-1 Simetryn .sup. 3 + 0.6 Echinochloa 43.1 20.8 72.6 54.94 17.66 phyllopogon 1-1 Simetryn  1 + 15 Echinochloa 8.3 45.3 68.2 49.84 18.36 phyllopogon 1-1 Prometryn .sup. 3 + 0.6 Echinochloa 43.1 21.5 72.6 55.33 17.27 phyllopogon 1-1 Prometryn  1 + 20 Echinochloa 8.3 68.2 85.6 70.84 14.76 phyllopogon 1-1 Pyraclonil  5 + 15 Sagittaria 33.5 72.5 99.6 81.71 17.89 trifolia 1-1 Bromoxynil 1 + 3 Sagittaria 10.9 12.5 38.3 22.04 16.26 octanoate trifolia 1-1 Carfentrazone- .sup. 1 + 0.2 Echinochloa 8.3 5.3 30.2 13.16 17.04 ethyl phyllopogon 1-1 Carfentrazone- 2 + 8 Echinochloa 18.7 73.6 93.6 78.54 15.06 ethyl phyllopogon 1-1 Amicarbazone 15 + 3  Monochoria 23.9 23.3 67.2 41.63 25.57 vaginalis 1-1 Amicarbazone  5 + 10 Monochoria 9.6 51.6 76.1 56.25 19.85 vaginalis 1-1 Atrazine  3 + 15 Echinochloa 43.1 30.6 78.6 60.51 18.09 phyllopogon 1-1 Isoproturon .sup. 3 + 0.6 Echinochloa 43.1 20.3 70.6 54.65 15.95 phyllopogon 1-1 Isoproturon 3 + 3 Echinochloa 43.1 40.2 84.1 65.97 18.13 phyllopogon 1-1 Bromacil 3 + 3 Echinochloa 43.1 12.8 70.2 50.38 19.82 phyllopogon 1-1 Pyridate  5 + 15 Cyperus 30.6 53.2 86.7 67.52 19.18 difformis 1-1 Propanil  5 + 15 Cyperus 30.6 46.2 80.1 62.66 17.44 difformis 1-1 Oxadiazon 3 + 3 Echinochloa 43.1 14.3 72.5 51.24 21.26 phyllopogon 1-1 Oxadiazon  3 + 15 Echinochloa 43.1 41.3 79.6 66.60 13.00 phyllopogon 1-1 Oxadiargyl .sup. 3 + 0.6 Echinochloa 43.1 3.4 60.3 45.03 15.27 phyllopogon 1-1 Oxadiargyl  3 + 15 Echinochloa 43.1 35.3 78.6 63.19 15.41 phyllopogon 1-1 Bentazone 5 + 9 Cyperus 30.6 40.4 76.5 58.64 17.86 difformis 1-1 Oxyfluorfen .sup. 2 + 0.2 Echinochloa 18.7 6.7 46.7 24.15 22.55 phyllopogon 1-1 Oxyfluorfen 2 + 8 Echinochloa 18.7 76.5 98.6 80.89 17.71 phyllopogon 1-1 Pentoxazone 7.5 + 10  Monochoria 15.1 43.6 66.5 52.12 14.38 vaginalis 1-1 Metribuzin 2 + 3 Echinochloa 18.7 32.3 60.6 44.96 15.64 phyllopogon 1-1 Terbuthylazine  3 + 15 Echinochloa 43.1 18.6 71.6 53.68 17.92 phyllopogon 1-1 Chlortoluron .sup. 3 + 0.6 Echinochloa 43.1 18.3 70.6 53.51 17.09 phyllopogon 1-1 Chlortoluron  3 + 15 Echinochloa 43.1 57.6 93.8 75.87 17.93 phyllopogon 1-1 Fluorochloridone 3 + 3 Echinochloa 43.1 9.1 60.3 48.28 12.02 phyllopogon 1-1 Beflubutamid 7.5 + 5.sup.  Monochoria 15.1 40.3 65.2 49.31 15.89 vaginalis 1-1 Pyrazosulfuron- 7.5 + 1.sup.  Monochoria 15.1 75.6 93.6 79.28 14.32 ethyl vaginalis 1-1 Penoxsulam 1 + 1 Cyperus 6.2 66.4 83.2 68.48 14.72 difformis 1-1 Bispyribac- 5 + 1 Cyperus 30.6 70.4 93.7 79.46 14.24 sodium difformis 1-1 Metazosulfuron 7.5 + 1.sup.  Monochoria 15.1 25.6 50.5 36.83 13.67 vaginalis 1-1 Propyrisulfuron .sup. 1 + 1.5 Cyperus 6.2 46.3 63.8 49.63 14.17 difformis 1-1 Triafamone  15 + 0.5 Monochoria 23.9 16.3 70.2 36.30 33.90 vaginalis 1-1 Triafamone 15 + 1  Monochoria 23.9 29.6 69.5 46.43 23.07 vaginalis 1-1 Butralin 1 + 3 Cyperus 6.2 16.4 38.5 21.58 16.92 difformis 1-1 Pendimethalin  5 + 30 Cyperus 30.6 40.3 79.5 58.57 20.93 difformis 1-1 Sanzuohuangcaotong 5 + 3 Monochoria 9.6 21.5 46.6 29.04 17.56 (   ) vaginalis 1-1 Shuangzuocaotong .sup. 3 + 0.6 Echinochloa 43.1 7.8 70.5 47.54 22.96 (   ) phyllopogon 1-1 Shuangzuocaotong 2 + 8 Echinochloa 18.7 70.9 95.6 76.34 19.26 (   ) phyllopogon 1-1 Huanbifucaotong  15 + 0.5 Leptochloa 20.3 9.2 46.7 27.63 19.07 (      ) chinensis 1-1 Mesotrione 5 + 1 Cyperus 30.6 50.4 85.7 65.58 20.12 difformis 1-1 Benzobicylon 5 + 3 Leptochloa 3.8 26.8 46.3 29.58 16.72 chinensis 1-1 Benzobicylon  5 + 15 Leptochloa 3.8 68.2 88.5 69.41 19.09 chinensis 1-1 Tefuryltrione 1 + 1 Cyperus 6.2 37.4 55.9 41.28 14.62 difformis 1-1 Molinate 3 + 3 Echinochloa 43.1 7.8 63.5 47.54 15.96 phyllopogon 1-1 Benthiocarb 5 + 3 Cyperus 30.6 15.2 60.9 41.15 19.75 difformis 1-1 Butachlor  3 + 15 Echinochloa 43.1 19.3 72.3 54.08 18.22 phyllopogon 1-1 Pretilachlor 3 + 3 Echinochloa 43.1 15.2 70.5 51.75 18.75 phyllopogon 1-1 Pretilachlor  3 + 15 Echinochloa 43.1 43.2 85.5 67.68 17.82 phyllopogon 1-1 Mefenacet 2 + 3 Echinochloa 18.7 19.2 56.3 34.31 21.99 phyllopogon 1-1 Mefenacet  3 + 15 Echinochloa 43.1 46.7 90.1 69.67 20.43 phyllopogon 1-1 Fentrazamide 15 + 3  Monochoria 23.9 30.2 62.5 46.88 15.62 vaginalis 1-1 Metolachlor 3 + 3 Echinochloa 43.1 7.8 67.5 47.54 19.96 phyllopogon 1-1 Anilofos 15 + 3  Leptochloa 20.3 30.8 70.2 44.85 25.35 chinensis 1-1 Piperophos 15 + 3  Monochoria 23.9 9.9 50.6 31.43 19.17 vaginalis 1-1 Pyroxasulfone 6 + 9 Monochoria 12.3 34.5 60.5 42.56 17.94 vaginalis 1-1 Cyhalofop- 3 + 3 Echinochloa 43.1 12.2 70.3 50.04 20.26 butyl phyllopogon 1-1 Metamifop .sup. 3 + 0.6 Echinochloa 43.1 6.8 70.5 46.97 23.53 phyllopogon 1-1 Metamifop 2 + 8 Echinochloa 18.7 60.9 82.6 68.21 14.39 phyllopogon 1-1 Clomazone 15 + 15 Leptochloa 20.3 53.6 82.6 63.02 19.58 chinensis 1-1 Cinmethylin 3 + 3 Echinochloa 43.1 13.2 68.3 50.61 17.69 phyllopogon 1-1 Indanofan 5 + 5 Monochoria 9.6 20.8 50.9 28.40 22.50 vaginalis 1-1 Oxaziclomefone .sup. 3 + 0.6 Echinochloa 43.1 12.5 70.1 50.21 19.89 phyllopogon 1-1 Oxaziclomefone 1 + 1 Echinochloa 8.3 18.7 46.2 25.45 20.75 phyllopogon Note: mu is a unit of land area in China, fifteen mus equal one hectare, i.e., 1 mu = 1/15 ha.

TABLE-US-00012 TABLE 10 Evaluation of actual control effects and combined effects of the mixtures of active ingredients (i) and (ii) in weeds (Gowing method) Active Control effect Control effect Ingredient Active (i) + (ii) of (i)alone of (ii) alone (i)/Comp. Ingredient g at corresponding at corresponding E E0 E − E0 No. (ii) a.i./mu Weed type dose (%) dose (%) (%) (%) (%) 1-2 Florpyrauxifen- .sup. 3 + 0.6 Echinochloa 53.7 21.5 80.1 63.65 16.45 benzyl phyllopogon 1-2 Florpyrauxifen- 1 + 3 Echinochloa 12.6 70.5 88.5 74.22 14.28 benzyl phyllopogon 1-2 Fluroxypyr 15 + 3  Monochoria 30.9 60.3 85.3 72.57 12.73 vaginalis 1-2 Fluroxypyr 5 + 5 Monochoria 7.8 73.4 93.5 75.47 18.03 vaginalis 1-2 MCPA 15 + 3  Monochoria 30.9 28.2 70.3 50.39 19.91 vaginalis 1-2 MCPA 5 + 3 Monochoria 7.8 28.2 51.2 33.80 17.40 vaginalis 1-2 2,4-D butyric 15 + 3  Monochoria 30.9 23.5 66.7 47.14 19.56 acid vaginalis 1-2 2,4-D butyric  3 + 15 Monochoria 7.8 65.3 83.8 68.01 15.79 acid vaginalis 1-2 Dicamba 5 + 3 Monochoria 7.8 50.9 71.3 54.73 16.57 vaginalis 1-2 Dicamba 5 + 5 Monochoria 7.8 70.2 87.9 72.52 15.38 vaginalis 1-2 Quinclorac 2 + 3 Echinochloa 26.8 35.2 69.5 52.57 16.93 phyllopogon 1-2 Quinclorac  3 + 15 Echinochloa 53.7 52.9 93.6 78.19 15.41 phyllopogon 1-2 Quintrione 1 + 3 Digitaria 18.2 15.2 46.9 30.63 16.27 sanguinalis 1-2 Clopyralid 5 + 1 Monochoria 7.8 49.6 70.5 53.53 16.97 vaginalis 1-2 Simetryn .sup. 3 + 0.6 Echinochloa 53.7 20.8 77.6 63.33 14.27 phyllopogon 1-2 Simetryn  1 + 15 Echinochloa 12.6 45.3 65.2 52.19 13.01 phyllopogon 1-2 Prometryn .sup. 3 + 0.6 Echinochloa 53.7 21.5 78.6 63.65 14.95 phyllopogon 1-2 Prometryn  1 + 20 Echinochloa 12.6 68.2 87.3 72.21 15.09 phyllopogon 1-2 Pyraclonil  3 + 15 Sagittaria 50.3 72.5 99.6 86.33 13.27 trifolia L. 1-2 Bromoxynil 1 + 3 Sagittaria 19.7 12.5 49.3 29.74 19.56 octanoate trifolia L. 1-2 Carfentrazone- .sup. 1 + 0.2 Echinochloa 12.6 5.3 34.2 17.23 16.97 ethyl phyllopogon 1-2 Carfentrazone- 2 + 8 Echinochloa 26.8 73.6 95.6 80.68 14.92 ethyl phyllopogon 1-2 Amicarbazone 15 + 3  Monochoria 30.9 23.3 65.2 47.00 18.20 vaginalis 1-2 Amicarbazone  5 + 10 Monochoria 7.8 51.6 75.1 55.38 19.72 vaginalis 1-2 Atrazine  3 + 15 Echinochloa 53.7 30.6 83.6 67.87 15.73 phyllopogon 1-2 Isoproturon .sup. 3 + 0.6 Echinochloa 53.7 20.3 79.6 63.10 16.50 phyllopogon 1-2 Isoproturon 3 + 3 Echinochloa 53.7 40.2 86.1 72.31 13.79 phyllopogon 1-2 Bromacil 3 + 3 Echinochloa 53.7 12.8 75.1 59.63 15.47 phyllopogon 1-2 Pyridate  5 + 15 Cyperus 36.5 53.2 88.2 70.28 17.92 difformis 1-2 Propanil  5 + 15 Cyperus 36.5 46.2 81.1 65.84 15.26 difformis 1-2 Oxadiazon 3 + 3 Echinochloa 53.7 14.3 76.5 60.32 16.18 phyllopogon 1-2 Oxadiazon  3 + 15 Echinochloa 53.7 41.3 87.6 72.82 14.78 phyllopogon 1-2 Oxadiargyl .sup. 3 + 0.6 Echinochloa 53.7 3.4 72.3 55.27 17.03 phyllopogon 1-2 Bentazone 5 + 9 Cyperus 36.5 40.4 76.5 62.15 14.35 difformis 1-2 Oxyfluorfen 2 + 8 Echinochloa 26.8 76.5 96.6 82.80 13.80 phyllopogon 1-2 Pentoxazone  5 + 10 Monochoria 7.8 43.6 63.5 48.00 15.50 vaginalis 1-2 Metribuzin 2 + 3 Echinochloa 26.8 32.3 67.6 50.44 17.16 phyllopogon 1-2 Terbuthylazine  3 + 15 Echinochloa 53.7 18.6 78.6 62.31 16.29 phyllopogon 1-2 Chlortoluron .sup. 3 + 0.6 Echinochloa 53.7 18.3 79.6 62.17 17.43 phyllopogon 1-2 Chlortoluron  3 + 15 Echinochloa 53.7 57.6 92.8 80.37 12.43 phyllopogon 1-2 Fluorochloridone 3 + 3 Echinochloa 53.7 9.1 72.3 57.91 14.39 phyllopogon 1-2 Beflubutamid 5 + 5 Monochoria 7.8 40.3 60.2 44.96 15.24 vaginalis 1-2 Pyrazosulfuron- 5 + 1 Monochoria 7.8 75.6 90.6 77.50 13.10 ethyl vaginalis 1-2 Penoxsulam 1 + 1 Cyperus 7.8 66.4 85.2 69.02 16.18 difformis 1-2 Bispyribac- 5 + 1 Cyperus 36.5 70.4 95.6 81.20 14.40 sodium difformis 1-2 Metazosulfuron 5 + 1 Monochoria 7.8 25.6 49.5 31.40 18.10 vaginalis 1-2 Propyrisulfuron .sup. 1 + 1.5 Cyperus 7.8 46.3 65.8 50.49 15.31 difformis 1-2 Triafamone 15 + 1  Monochoria 30.9 29.6 67.5 51.35 16.15 vaginalis 1-2 Butralin 1 + 3 Cyperus 7.8 16.4 44.5 22.92 21.58 difformis 1-2 Pendimethalin  5 + 30 Cyperus 36.5 40.3 78.5 62.09 16.41 difformis 1-2 Sanzuohuangcaotong 5 + 3 Monochoria 7.8 21.5 43.6 27.62 15.98 (   ) vaginalis 1-2 Shuangzuocaotong 2 + 8 Digitaria 40.6 75.1 98.6 85.21 13.39 (   ) sanguinalis 1-2 Huanbifucaotong 1 + 3 Digitaria 18.2 6.2 40.7 23.27 17.43 (   ) sanguinalis 1-2 Mesotrione 5 + 1 Cyperus 36.5 50.4 82.7 68.50 14.20 difformis 1-2 Benzobicylon 5 + 3 Leptochloa 6.5 26.8 44.3 31.56 12.74 chinensis 1-2 Benzobicylon  5 + 15 Leptochloa 6.5 68.2 87.2 70.27 16.93 chinensis 1-2 Tefuryltrione 1 + 1 Cyperus 7.8 37.4 58.9 42.28 16.62 difformis 1-2 Molinate 3 + 3 Echinochloa 53.7 7.8 73.8 57.31 16.49 phyllopogon 1-2 Benthiocarb 5 + 3 Cyperus 36.5 15.2 63.9 46.15 17.75 difformis 1-2 Butachlor  3 + 15 Echinochloa 53.7 19.3 77.3 62.64 14.66 phyllopogon 1-2 Pretilachlor 3 + 3 Echinochloa 53.7 15.2 76.2 60.74 15.46 phyllopogon 1-2 Pretilachlor  3 + 15 Echinochloa 53.7 43.2 87.6 73.70 13.90 phyllopogon 1-2 Mefenacet 2 + 3 Echinochloa 26.8 19.2 59.3 40.85 18.45 phyllopogon 1-2 Mefenacet  3 + 15 Echinochloa 53.7 46.7 95.1 75.32 19.78 phyllopogon 1-2 Fentrazamide 15 + 3  Monochoria 30.9 30.2 69.5 51.77 17.73 vaginalis 1-2 Metolachlor 3 + 3 Digitaria 65.3 15.3 89.5 70.61 18.89 sanguinalis 1-2 Anilofos 15 + 3  Leptochloa 30.6 30.8 79.2 51.98 27.22 chinensis 1-2 Piperophos 15 + 3  Monochoria 30.9 9.9 53.6 37.74 15.86 vaginalis 1-2 Cyhalofop- 3 + 3 Echinochloa 53.7 12.2 76.3 59.35 16.95 butyl phyllopogon 1-2 Metamifop .sup. 3 + 0.6 Echinochloa 53.7 6.8 75.9 56.85 19.05 phyllopogon 1-2 Metamifop 2 + 8 Echinochloa 26.8 60.9 87.6 71.38 16.22 phyllopogon 1-2 Clomazone 15 + 15 Leptochloa 30.6 53.6 85.8 67.80 18.00 chinensis 1-2 Cinmethylin 3 + 3 Echinochloa 53.7 13.2 75.3 59.81 15.49 phyllopogon 1-2 Indanofan 5 + 5 Monochoria 7.8 20.8 48.9 26.98 21.92 vaginalis 1-2 Oxaziclomefone .sup. 3 + 0.6 Echinochloa 53.7 12.5 79.1 59.49 19.61 phyllopogon 1-2 Oxaziclomefone 1 + 1 Echinochloa 12.6 18.7 50.2 28.94 21.26 phyllopogon Note: mu is a unit of land area in China, fifteen mus equal one hectare, i.e., 1 mu = 1/15 ha.

TABLE-US-00013 TABLE 11 Evaluation of actual control effects and combined effects of the mixtures of activity ingredient (i) and (ii) in weeds (Gowing method) Activity Control effect Control effect Ingredient Activity (i) + (ii) of (i)alone of (ii) alone (i)/Comp. Ingredient g at corresponding at corresponding E E0 E − E0 No. (ii) a.i./mu Weed type dose (%) dose (%) (%) (%) (%) 1-4 Florpyrauxifen- .sup. 3 + 0.6 Echinochloa 60.2 21.5 89.1 68.8 20.3 benzyl phyllopogon 1-4 Florpyrauxifen- 0.6 + 3.sup.  Echinochloa 20.5 70.5 100 76.5 23.5 benzyl phyllopogon 1-4 Fluroxypyr 15 + 3  Monochoria 40.5 60.3 98 76.4 21.6 vaginalis 1-4 Fluroxypyr 0.8 + 4.sup.  Monochoria 5.8 70.4 100 72.1 27.9 vaginalis 1-4 MCPA 15 + 3  Monochoria 40.5 28.2 80.6 57.3 23.3 vaginalis 1-4 MCPA 3 + 3 Monochoria 12.7 28.2 64.5 37.3 27.2 vaginalis 1-4 2,4-D butyric 15 + 3  Monochoria 40.5 23.5 75 54.5 20.5 acid vaginalis 1-4 2,4-D butyric  3 + 15 Monochoria 12.7 65.3 86 69.7 16.3 acid vaginalis 1-4 Dicamba 3 + 3 Monochoria 12.7 50.9 84.5 57.1 27.4 vaginalis 1-4 Dicamba 1 + 5 Monochoria 6.2 70.2 98 72.0 26.0 vaginalis 1-4 Quinclorac 3 + 3 Echinochloa 60.2 35.2 96.3 74.2 22.1 phyllopogon 1-4 Quinclorac  3 + 15 Echinochloa 60.2 52.9 100 81.3 18.7 phyllopogon 1-4 Quintrione 3 + 3 Echinochloa 60.2 15.8 90.5 66.5 24.0 phyllopogon 1-4 Quintrione 1.5 + 30  Echinochloa 41.5 66.7 92.6 80.5 12.1 phyllopogon 1-4 Clopyralid .sup. 6 + 1.2 Monochoria 28.6 56.3 83.5 68.8 14.7 vaginalis 1-4 Clopyralid 1 + 1 Monochoria 6.2 49.6 75.5 52.7 22.8 vaginalis 1-4 Simetryn .sup. 3 + 0.6 Echinochloa 60.2 20.8 85.6 68.5 17.1 phyllopogon 1-4 Simetryn  3 + 15 Echinochloa 60.2 45.3 93.1 78.2 14.9 phyllopogon 1-4 Prometryn .sup. 3 + 0.6 Echinochloa 60.2 21.5 90.6 68.8 21.8 phyllopogon 1-4 Prometryn  1 + 20 Echinochloa 36.6 68.2 96.6 79.8 16.8 phyllopogon 1-4 Pyraclonil .sup. 3 + 0.6 Sagittaria 60.3 9.3 90.6 64.0 26.6 trifolia L. 1-4 Pyraclonil 0.75 + 15.sup.  Sagittaria 16.3 72.5 92.6 77.0 15.6 trifolia L. 1-4 Bromoxynil .sup. 3 + 0.6 Sagittaria 60.3 6.4 86.9 62.8 24.1 octanoate trifolia L. 1-4 Bromoxynil 3 + 3 Sagittaria 60.3 12.5 92.3 65.3 27.0 octanoate trifolia L. 1-4 Carfentrazone- .sup. 3 + 0.2 Echinochloa 60.2 5.3 82.2 62.3 19.9 ethyl phyllopogon 1-4 Carfentrazone- 0.7 + 8.sup.  Echinochloa 25.1 73.6 93 80.2 12.8 ethyl phyllopogon 1-4 Amicarbazone 15 + 3  Monochoria 40.5 23.3 80.6 54.4 26.2 vaginalis 1-4 Amicarbazone 3.5 + 10  Monochoria 13.3 51.6 80.1 58.0 22.1 vaginalis 1-4 Atrazine .sup. 3 + 0.6 Echinochloa 60.2 2.3 83.6 61.1 22.5 phyllopogon 1-4 Atrazine 0.75 + 15.sup.  Echinochloa 30.3 30.6 70.6 51.6 19.0 phyllopogon 1-4 Isoproturon .sup. 3 + 0.6 Echinochloa 60.2 20.3 90.6 68.3 22.3 phyllopogon 1-4 Isoproturon 3 + 3 Echinochloa 60.2 40.2 94.3 76.2 18.1 phyllopogon 1-4 Bromacil 3 + 3 Echinochloa 60.2 12.8 87.6 65.3 22.3 phyllopogon 1-4 Bromacil 1.5 + 30  Echinochloa 41.5 59.7 93.7 76.4 17.3 phyllopogon 1-4 Pyridate .sup. 9 + 1.8 Cyperus 32.1 12.9 68.6 40.9 27.7 difformis 1-4 Pyridate  3 + 15 Cyperus 15.2 53.2 83.5 60.3 23.2 difformis 1-4 Propanil .sup. 9 + 1.8 Cyperus 32.1 9.2 63.6 38.3 25.3 difformis 1-4 Propanil  3 + 15 Cyperus 15.2 46.2 73.5 54.4 19.1 difformis 1-4 Oxadiazon 3 + 3 Echinochloa 60.2 14.3 90.5 65.9 24.6 phyllopogon 1-4 Oxadiazon 0.75 + 15.sup.  Echinochloa 30.3 41.3 86.6 59.1 27.5 phyllopogon 1-4 Oxadiargyl .sup. 3 + 0.6 Echinochloa 60.2 3.4 83.3 61.6 21.7 phyllopogon 1-4 Oxadiargyl 0.75 + 15.sup.  Echinochloa 30.3 35.3 78.6 54.9 23.7 phyllopogon 1-4 Bentazone .sup. 9 + 1.8 Cyperus 32.1 18.2 65.6 44.5 21.1 difformis 1-4 Bentazone 9 + 9 Cyperus 32.1 40.4 80.5 59.5 21.0 difformis 1-4 Oxyfluorfen .sup. 3 + 0.2 Echinochloa 60.2 6.7 86.7 62.9 23.8 phyllopogon 1-4 Oxyfluorfen 0.7 + 8.sup.  Echinochloa 25.1 76.5 95.4 82.4 13.0 phyllopogon 1-4 Pentoxazone  15 + 0.5 Monochoria 40.5 6.4 73.6 44.3 29.3 vaginalis 1-4 Pentoxazone 10 + 10 Monochoria 31.7 43.6 90.5 61.5 29.0 vaginalis 1-4 Metribuzin .sup. 3 + 0.6 Echinochloa 60.2 9.1 86.9 63.8 23.1 phyllopogon 1-4 Metribuzin 3 + 3 Echinochloa 60.2 32.3 90.6 73.1 17.5 phyllopogon 1-4 Terbuthylazine .sup. 3 + 0.6 Echinochloa 60.2 0.95 80.2 60.6 19.6 phyllopogon 1-4 Terbuthylazine  3 + 15 Echinochloa 60.2 18.6 91.4 67.6 23.8 phyllopogon 1-4 Chlortoluron .sup. 3 + 0.6 Echinochloa 60.2 18.3 85.6 67.5 18.1 phyllopogon 1-4 Chlortoluron 0.75 + 15.sup.  Echinochloa 30.3 57.6 91.5 70.4 21.1 phyllopogon 1-4 Fluorochloridone 3 + 3 Echinochloa 60.2 9.1 90.3 63.8 26.5 phyllopogon 1-4 Fluorochloridone 1.5 + 30  Echinochloa 41.5 52.3 87.7 72.1 15.6 phyllopogon 1-4 Beflubutamid  15 + 1.5 Monochoria 40.5 15.3 73.6 49.6 24.0 vaginalis 1-4 Beflubutamid 5 + 5 Monochoria 19.6 40.3 80.3 52.0 28.3 vaginalis 1-4 Pyrazosulfuron- .sup. 3 + 0.6 Monochoria 12.7 54.5 83.1 60.3 22.8 ethyl vaginalis 1-4 Pyrazosulfuron- 1 + 1 Monochoria 6.2 75.6 90.6 77.1 13.5 ethyl vaginalis 1-4 Penoxsulam .sup. 9 + 1.8 Cyperus 32.1 80.2 100 86.6 13.4 difformis 1-4 Penoxsulam 1 + 1 Cyperus 6.3 66.4 85.7 68.5 17.2 difformis 1-4 Bispyribac- .sup. 9 + 0.6 Cyperus 32.1 39.5 77.3 58.9 18.4 sodium difformis 1-4 Bispyribac- 1 + 1 Cyperus 6.3 70.4 88.6 72.3 16.3 sodium difformis 1-4 Metazosulfuron .sup. 6 + 1.2 Monochoria 28.6 30.3 81.5 68.8 12.7 vaginalis 1-4 Metazosulfuron 1 + 1 Monochoria 6.2 25.6 76.5 52.7 23.8 vaginalis 1-4 Propyrisulfuron .sup. 9 + 0.6 Cyperus 32.1 19.5 57.3 45.3 12.0 difformis 1-4 Propyrisulfuron 0.3 + 1.5 Cyperus 4.1 46.3 63.5 48.5 15.0 difformis 1-4 Triafamone  15 + 0.5 Monochoria 40.5 16.3 70.6 50.2 20.4 vaginalis 1-4 Triafamone 1 + 1 Monochoria 6.2 29.6 60.5 34.0 26.5 vaginalis 1-4 Butralin 3 + 3 Cyperus 15.2 16.4 58.5 29.1 29.4 difformis 1-4 Butralin 1.5 + 30  Cyperus 9.2 46.8 75.3 51.7 23.6 difformis 1-4 Pendimethalin .sup. 9 + 1.8 Cyperus 32.1 6.3 62.6 36.4 26.2 difformis 1-4 Pendimethalin  6 + 30 Cyperus 25.6 40.3 76.5 55.6 20.9 difformis 1-4 Sanzuohuangcaotong 15 + 3  Monochoria 40.5 21.5 79.6 53.3 26.3 (   ) vaginalis 1-4 Sanzuohuangcaotong 6 + 6 Monochoria 28.6 40.1 83 57.2 25.8 (   ) vaginalis 1-4 Shuangzuocaotong .sup. 3 + 0.6 Echinochloa 60.2 7.8 83.5 63.3 20.2 (   ) phyllopogon 1-4 Shuangzuocaotong 1.6 + 8.sup.  Echinochloa 45.3 70.9 98.6 84.1 14.5 (   ) phyllopogon 1-4 Huanbifucaotong  15 + 0.5 Leptochloa 45.6 9.2 68.7 50.6 18.1 (      ) chinensis 1-4 Huanbifucaotong  3 + 15 Leptochloa 18.6 76.2 100 80.6 19.4 (      ) chinensis 1-4 Mesotrione .sup. 9 + 0.6 Cyperus 32.1 29.5 67.3 52.1 15.2 difformis 1-4 Mesotrione 1 + 1 Cyperus 6.3 50.4 68.6 53.5 15.1 difformis 1-4 Benzobicylon 15 + 3  Leptochloa 45.6 26.8 76.3 60.2 16.1 chinensis 1-4 Benzobicylon  3 + 15 Leptochloa 18.6 68.2 98.6 74.1 24.5 chinensis 1-4 Tefuryltrione .sup. 9 + 1.8 Cyperus 32.1 63.2 89.6 75.0 14.6 difformis 1-4 Tefuryltrione 1 + 1 Cyperus 6.3 37.4 58.7 41.3 17.4 difformis 1-4 Molinate 3 + 3 Echinochloa 60.2 7.8 76.5 63.3 13.2 phyllopogon 1-4 Molinate 1.5 + 30  Echinochloa 41.5 40.6 78.5 65.3 13.2 phyllopogon 1-4 Benthiocarb 3 + 3 Cyperus 15.2 15.2 53.5 28.1 25.4 difformis 1-4 Benthiocarb 1.5 + 30  Cyperus 9.2 50.3 70.3 54.9 15.4 difformis 1-4 Butachlor  3 + 15 Echinochloa 60.2 19.3 85.5 67.9 17.6 phyllopogon 1-4 Butachlor 0.6 + 30  Echinochloa 20.5 39.7 65.2 52.1 13.1 phyllopogon 1-4 Pretilachlor 3 + 3 Echinochloa 60.2 15.2 85.3 66.2 19.1 phyllopogon 1-4 Pretilachlor 0.75 + 15.sup.  Echinochloa 30.3 43.2 80.5 60.4 20.1 phyllopogon 1-4 Mefenacet 3 + 3 Echinochloa 60.2 19.2 80.3 67.8 12.5 phyllopogon 1-4 Mefenacet  3 + 15 Echinochloa 60.2 46.7 96.1 78.8 17.3 phyllopogon 1-4 Fentrazamide  15 + 1.5 Monochoria 40.5 18.3 65.6 51.4 14.2 vaginalis 1-4 Fentrazamide 15 + 3  Monochoria 40.5 30.2 73.5 58.5 15.0 vaginalis 1-4 Metolachlor 3 + 3 Echinochloa 60.2 7.8 80.5 63.3 17.2 phyllopogon 1-4 Metolachlor  3 + 15 Echinochloa 60.2 15.3 87.5 66.3 21.2 phyllopogon 1-4 Anilofos 15 + 3  Leptochloa 45.6 30.8 100 62.4 37.6 chinensis 1-4 Anilofos  3 + 30 Leptochloa 18.6 62.6 100 69.6 30.4 chinensis 1-4 Piperophos 15 + 3  Monochoria 40.5 9.9 65.6 46.4 19.2 vaginalis 1-4 Piperophos  1 + 30 Monochoria 6.2 41.2 68.2 44.8 23.4 vaginalis 1-4 Pyroxasulfone  15 + 0.5 Monochoria 40.5 6.3 66.4 44.2 22.2 vaginalis 1-4 Pyroxasulfone 1.8 + 9.sup.  Monochoria 8.6 34.5 63.5 40.1 23.4 vaginalis 1-4 Cyhalofop- 3 + 3 Echinochloa 60.2 12.2 80.3 65.1 15.2 butyl phyllopogon 1-4 Cyhalofop- 0.75 + 15.sup.  Echinochloa 30.3 45.1 80.9 61.7 19.2 butyl phyllopogon 1-4 Metamifop .sup. 3 + 0.6 Echinochloa 60.2 6.8 83.5 62.9 20.6 phyllopogon 1-4 Metamifop 1.6 + 8.sup.  Echinochloa 45.3 60.9 96.6 78.6 18.0 phyllopogon 1-4 Clomazone 15 + 3  Leptochloa 45.6 16.8 80.6 54.7 25.9 chinensis 1-4 Clomazone  3 + 15 Leptochloa 18.6 53.6 90.4 62.2 28.2 chinensis 1-4 Cinmethylin 3 + 3 Echinochloa 60.2 13.2 82.3 65.5 16.8 phyllopogon 1-4 Cinmethylin 0.75 + 15.sup.  Echinochloa 30.3 54.5 85.7 68.3 17.4 phyllopogon 1-4 Indanofan 5 + 5 Monochoria 19.6 20.8 60.3 36.3 24.0 vaginalis 1-4 Indanofan 2.4 + 12  Monochoria 10.2 63.1 80 66.9 13.1 vaginalis 1-4 Oxaziclomefone .sup. 3 + 0.6 Echinochloa 60.2 12.5 83.1 65.2 17.9 phyllopogon 1-4 Oxaziclomefone 1 + 1 Echinochloa 36.6 18.7 70.6 48.5 22.1 phyllopogon Note: mu is a unit of land area in China, fifteen mus equal one hectare, i.e., 1 mu = 1/15 ha.

[0218] In addition, Table B1 lists specific combinations of other activity ingredients (i) and (ii), further illustrating the compositions of the present invention. The compounds in the column “activity Ingredient (i)/Compound No.” are listed in the index Table A1. The second column of Table B1 lists compounds of the particular activity ingredient (ii) (e.g., “Pyrazosulfuron-ethyl” in the first row). The remaining rows of Table B1 are constructed similarly.

TABLE-US-00014 TABLE B1 List of ingredients in the compositions Activity Ingredient (i)/ Compound. No. Activity Ingredient (ii) 1-3 Pyrazosulfuron-ethyl 1-3 Penoxsulam 1-3 Bispyribac-sodium 1-3 Pyriminob ac-methyl 1-3 Metazosulfuron 1-3 Propyrisulfuron 1-3 Triafamone 1-3 Cyhalofop-butyl 1-3 Metamifop 1-3 Quinclorac 1-3 MCPA 1-3 2,4-D 1-3 2,4-D butyric acid 1-3 Fluroxypyr 1-3 Florpyrauxifen-benzyl 1-3 MCPA butyric acid 1-3 Dicamba 1-3 Quintrione 1-3 Clopyralid 1-3 Trichlopyr 1-3 Pendimethalin 1-3 Butralin 1-3 Benthiocarb 1-3 Molinate 1-3 Sanzuohuangcaotong 1-3 Shuangzuocaotong 1-3 Huanbifucaotong 1-3 Mesotrione 1-3 Benzobicylon 1-3 Tefuryltrione 1-3 Diflufenican 1-3 Fluorochloridone 1-3 Beflubutamid 1-3 Carfentrazone-ethyl 1-3 Pyraclonil 1-3 Oxadiazon 1-3 Oxadiargyl 1-3 Oxyfluorfen 1-3 Pentoxazone 1-3 Butachlor 1-3 Pretilachlor 1-3 Mefenacet 1-3 Anilofos 1-3 Fentrazamide 1-3 Metolachlor 1-3 Piperophos 1-3 Pyroxasulfone 1-3 Simetryn 1-3 Prometryn 1-3 Amicarbazone 1-3 Isoproturon 1-3 Bromacil 1-3 Pyridate 1-3 Chlortoluron 1-3 Bentazone 1-3 Prop anil 1-3 Metribuzin 1-3 Atrazine 1-3 Bromoxynil 1-3 Bromoxynil octanoate 1-3 Terbuthylazine 1-3 Clomazone 1-3 Oxaziclomefone 1-3 Cinmethylin 1-3 Indanofan

[0219] Table B2 is constructed in the same manner as the above Table B1, except that the first column “Activity Ingredient (i)/Comp. No.” are replaced by the corresponding “Activity Ingredient (i)/Comp. No.” column as shown below. The compounds in the “Activity Ingredient (i)/Comp. No.” column are listed in the Tables A1-A152. Accordingly, for example, in Table B2, the “Activity Ingredient (i)/Comp. No.” of the first column are all “1-5” (i.e., Compound 1-5 identified in the Table A1), and the first row below the column heading of Table B2 specifically discloses a mixture of Compound 1-5 and “Pyrazosulfuron-ethyl”. Tables B3 to B167 are similarly constructed.

TABLE-US-00015 “Activity “Activity “Activity “Activity Ingredient Ingredient Ingredient Ingredient (i)/Comp. (i)/Comp. (i)/Comp. (i)/Comp. Table No.” Table No.” Table No.” Table No.” B2 1-5  B3 1-6  B4 1-7  B5 1-8  B6 1-9  B7 1-10 B8 1-11 B9 1-12 B10 1-13 B11 1-14 B12 1-15 B13 1-16 B14 1-17 B15 1-18 B16 1-19 B17 1-20 B18 1-21 B19 1-22 B20 1-23 B21 1-24 B22 1-25 B23 1-26 B24 1-27 B25 1-28 B26 1-29 B27 1-30 B28 1-31 B29 1-32 B30 1-33 B31 1-34 B32 1-35 B33 1-36 B34 1-37 B35 1-38 B36 1-39 B37 1-40 B38 1-41 B39 1-42 B40 1-43 B41 1-44 B42 1-45 B43 1-46 B44 1-47 B45 1-48 B46 1-49 B47 1-50 B48 1-51 B49 1-52 B50 1-53 B51 1-54 B52 1-55 B53 1-56 B54 1-57 B55 1-58 B56 1-59 B57 1-60 B58 1-61 B59 1-62 B60 1-63 B61 1-64 B62 1-65 B63 1-66 B64 1-67 B65 1-68 B66 1-69 B67 1-70 B68 1-71 B69 1-72 B70 1-73 B71 1-74 B72 1-75 B73 1-76 B74 1-77 B75 1-78 B76 1-79 B77 1-80 B78 1-81 B79 1-82 B80 1-83 B81 1-84 B82 1-85 B83 1-86 B84 1-87 B85 1-88 B86 1-89 B87 1-90 B88 1-91 B89 1-92 B90 1-93 B91 1-94 B92 1-95 B93 1-96 B94 1-97 B95 1-98 B96 1-99 B97  1-100 B98  1-101 B99  1-102 B100  1-103 B101  1-104 B102  1-105 B103  1-106 B104  1-107 B105  1-108 B106  1-109 B107  1-110 B108  1-111 B109  1-112 B110  1-113 B111  1-114 B112  1-115 B113  1-116 B114  1-117 B115  1-118 B116  1-119 B117  1-120 B118  1-121 B119  1-122 B120  1-123 B121  1-124 B122  1-125 B123  1-126 B124  1-127 B125  1-128 B126  1-129 B127  1-130 B128  1-131 B129  1-132 B130  1-133 B131  1-134 B132  1-135 B133  1-136 B134  1-137 B135  1-138 B136  1-139 B137  1-140 B138  1-141 B139  1-142 B140  1-143 B141  1-144 B142  1-145 B143  1-146 B144  1-147 B145  1-148 B146 2-3  B147 2-4  B148 4-4  B149 6-4  B150 8-4  B151 10-4  B152 14-4  B153 17-4  B154 17-5  B155 18-4  B156 20-2  B157 20-4  B158 21-4  B159 21-5  B160 22-4  B161 24-4  B162 96-4  B163 96-5  B164 101-4   B165 101-5   B166 103-4   B167 103-5  

[0220] At the same time, it is found after several tests that the other mixtures of activity ingredients (i) and (ii) of the present invention could produce similar herbicidal effects. In addition, 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 wheat, corn, rice, sugarcane, soybean, cotton, oil sunflower, potato, orchards and vegetables in different herbicide application methods.