HETEROCYCLE-SUBSTITUTED AROMATIC COMPOUND, METHOD FOR PREPARING SAME, HERBICIDAL COMPOSITION, AND USE THEREOF

Abstract

The present invention belongs to the technical field of pesticides, and particularly, relates to a heterocycle-substituted aromatic compound, a method for preparing same, a herbicidal composition, and use thereof. The compound is represented by general formula I, wherein Y represents a halogen, a halogenated alkyl, cyano, nitro, or amino; Z represents hydrogen, a halogen, or hydroxyl; M.sub.1 and M.sub.2 each independently represent CR.sub.5 or N(O).sub.m; Q represents CX3X4; R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R5 each independently represent hydrogen, a halogen, or the like; X.sub.1, X.sub.2, X.sub.3, and X.sub.4 each independently represent hydrogen, a halogen, or the like, and m represents 0 or 1. The compound, even at a low application rate, has excellent herbicidal activity on gramineous weeds, broad-leaf weeds, and the like, and has high selectivity for crops.

##STR00001##

Claims

1. A heterocycle-substituted aromatic compound, as shown in the general formula I: ##STR00229## wherein, Y represents halogen, haloalkyl, cyano, nitro, or amino; Z represents hydrogen, halogen, or hydroxyl; M.sub.1 and M.sub.2 each independently represent CR.sub.5 or N(O).sub.m; Q represents CX.sub.3X.sub.4; R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 each independently represent hydrogen, halogen, hydroxyl, mercapto, formyl, hydroxylalkyl, nitro, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, OR.sub.11, SR.sub.11, (SO)R.sub.11, (SO.sub.2)R.sub.11, (SO.sub.2)OR.sub.11, O(SO.sub.2)R.sub.11, N(R.sub.12).sub.2, phenyl, or benzyl, wherein, the alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, or cycloalkenylalkyl is each independently unsubstituted or substituted by halogen; the phenyl or benzyl is each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylsulfanyl, alkylsulfonyl, alkoxy, and haloalkoxy; X.sub.1, X.sub.2, X.sub.3, and X.sub.4 each independently represent hydrogen, halogen, nitro, cyano, thiocyanato, hydroxyl, mercapto, sulfo, formyl, haloformyl, azido, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, PO(OR).sub.2, OR, (CO)R, SR, (SO)R, (SO.sub.2)R, Si(R).sub.3, O(CO)R, O(SO.sub.2)R, S(CO)R, (SO.sub.2)OR, O(CO)OR, (CO)(CO)OR, ##STR00230## CRNOH, CRNOR, heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, amino, aminoalkyl, aminocarbonylalkyl, aminocarbonyloxyalkyl, aminothiocarbonyloxyalkyl, aminosulfonyl, or aminosulfonyloxyalkyl, wherein, the alkyl, alkenyl, or alkynyl is each independently unsubstituted or substituted by at least one group selected from halogen, cyano, hydroxyl, mercapto, carboxyl, OR, (CO)R, SR, (SO.sub.2)R, O(CO)H, O(CO)R, O(SO.sub.2)R, (CO)OR, O(CO)OR, O(CO)(CO)OH, O(CO)(CO)OR, O-alkyl-(CO)OH, and O-alkyl-(CO)OR; the cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, or arylalkyl is each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O-alkyl-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; the amino, aminoalkyl, aminocarbonylalkyl, aminocarbonyloxyalkyl, aminothiocarbonyloxyalkyl, aminosulfonyl, or aminosulfonyloxyalkyl is each independently unsubstituted or substituted by one or two groups selected from R.sub.11, OR.sub.11, (CO)R.sub.11, (CO)OR.sub.11, -alkyl-(CO)OR.sub.11, (SO.sub.2)R.sub.11, (SO.sub.2)OR.sub.11, -alkyl-(SO.sub.2)R.sub.11, (CO)N(R.sub.12).sub.2, and (SO.sub.2)N(R.sub.12).sub.2; R each independently represents hydrogen, halogen, alkoxy, alkoxyalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclyl, or heterocyclylalkyl, wherein, the alkyl, alkenyl, or alkynyl is each independently unsubstituted or substituted by halogen; the cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclyl, or heterocyclylalkyl is each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O-alkyl-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; R each independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, arylalkenyl, heterocyclyl, heterocyclylalkyl, or heterocyclylalkenyl, wherein, the alkyl, alkenyl, or alkynyl is each independently unsubstituted or substituted by at least one group selected from halogen, cyano, trialkylsilyl, OR.sub.13, SR.sub.13, O(CO)R.sub.13, (CO)R.sub.13, (CO)OR.sub.13, and O(CO)OR.sub.13; the cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, arylalkenyl, heterocyclyl, heterocycylalkyl, or heterocyclylalkenyl is each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O-alkyl-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; W.sub.1 represents O, S, or NW.sub.4; W.sub.2 represents OW.sub.3, SW.sub.3, or NW.sub.4W.sub.5; W.sub.3 each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, ##STR00231## wherein, the alkyl, alkenyl, or alkynyl is each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, cycloalkyl, trialkylsilyl, cycloalkenyl, heterocyclyl, aryl, ##STR00232## the cycloalkyl, cycloalkenyl, heterocyclyl, or aryl is each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O-alkyl-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; W.sub.4 and W.sub.5 each independently represent hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, ##STR00233## wherein, the alkyl, alkenyl, or alkynyl is each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, cycloalkyl, trialkylsilyl, cycloalkenyl, heterocyclyl, aryl, ##STR00234## the cycloalkyl, cycloalkenyl, heterocyclyl, or aryl is each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O-alkyl-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; or NW.sub.4W.sub.5 represents ##STR00235## or unsubstituted or substituted heterocyclyl with a nitrogen atom at 1-position; X.sub.11 each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, or arylalkyl, wherein, the cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, or arylalkyl is each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O-alkyl-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; X.sub.12 each independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, or arylalkyl, wherein, the cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, or arylalkyl is each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O-alkyl-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; X.sub.13 and X.sub.14 each independently represent hydrogen, halogen, cyano, alkoxy, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclyl, or heterocyclylalkyl, or the group CX.sub.13X.sub.14 together forms an unsubstituted or substituted cyclic structure, or the group NX.sub.13X.sub.14 together forms an unsubstituted or substituted heterocyclyl with a nitrogen atom at 1-position, wherein, the alkyl, alkenyl, or alkynyl is each independently unsubstituted or substituted by halogen; the cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclyl, or heterocyclylalkyl is each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, alkyl-substituted cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O-alkyl-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; R.sub.11 each independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl, or benzyl, wherein, the alkyl, alkenyl, or alkynyl is each independently unsubstituted or substituted by halogen; the phenyl or benzyl is each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylsulfanyl, alkylsulfonyl, alkoxy, and haloalkoxy; R.sub.12 each independently represents hydrogen, alkyl, alkenyl, alkynyl, alkoxy, alkylsulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, or cycloalkenylalkyl, or the group N(R.sub.12).sub.2 in (CO)N(R.sub.12).sub.2 or (SO.sub.2)N(R.sub.12).sub.2 each independently represents unsubstituted or substituted heterocyclyl with a nitrogen atom at 1-position; R.sub.13 each independently represents alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, or phenyl that is substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, alkylsulfanyl, alkylsulfonyl, and phenoxy that is substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, and haloalkoxy; R.sub.14 each independently represents hydrogen, alkyl, haloalkyl, phenyl, or phenyl that is substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylsulfanyl, alkylsulfonyl, alkoxy, and haloalkoxy; m represents 0 or 1.

2. The heterocycle-substituted aromatic compound according to claim 1, wherein it is characterized in that, Y represents halogen, halo C1-C8 alkyl, cyano, nitro, or amino; preferably, Y represents halogen, halo C1-C6 alkyl, cyano, nitro, or amino.

3. The heterocycle-substituted aromatic compound according to claim 1, wherein it is characterized in that, R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 each independently represent hydrogen, halogen, hydroxyl, mercapto, formyl, hydroxyl C1-C8 alkyl, nitro, cyano, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, OR.sub.11, SR.sub.11, (SO)R.sub.11, (SO.sub.2)R.sub.11, (SO.sub.2)OR.sub.11, O(SO.sub.2)R.sub.11, N(R.sub.12).sub.2, phenyl, or benzyl, wherein, the C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, or C3-C8 cycloalkenyl C1-C8 alkyl is each independently unsubstituted or substituted by halogen; the phenyl or benzyl is each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylsulfanyl, C1-C8 alkylsulfonyl, C1-C8 alkoxy, and halo C1-C8 alkoxy; preferably, R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 each independently represent hydrogen, halogen, hydroxyl, mercapto, formyl, hydroxyl C1-C6 alkyl, nitro, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, OR.sub.11, SR.sub.11, (SO)R.sub.11, (SO.sub.2)R.sub.11, (SO.sub.2)OR.sub.11, O(SO.sub.2)R.sub.11, N(R.sub.12).sub.2, phenyl, or benzyl, wherein, the C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, or C3-C6 cycloalkenyl C1-C6 alkyl is each independently unsubstituted or substituted by halogen; the phenyl or benzyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfonyl, C1-C6 alkoxy, and halo C1-C6 alkoxy; more preferably, R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 each independently represent hydrogen, halogen, hydroxyl, mercapto, formyl, hydroxyl C1-C6 alkyl, nitro, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, OR.sub.11, SR.sub.11, (SO)R.sub.11, (SO.sub.2)R.sub.11, (SO.sub.2)OR.sub.11, O(SO.sub.2)R.sub.11, N(R.sub.12).sub.2, phenyl, or benzyl, wherein, the C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, or C3-C6 cycloalkenyl C1-C3 alkyl is each independently unsubstituted or substituted by halogen; the phenyl or benzyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfonyl, C1-C6 alkoxy, and halo C1-C6 alkoxy.

4. The heterocycle-substituted aromatic compound according to claim 1, wherein it is characterized in that, X.sub.1, X.sub.2, X.sub.3, and X.sub.4 each independently represent hydrogen, halogen, nitro, cyano, thiocyanato, hydroxyl, mercapto, sulfo, formyl, haloformyl, azido, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, PO(OR).sub.2, OR, (CO)R, SR, (SO)R, (SO.sub.2)R, Si(R).sub.3, O(CO)R, O(SO.sub.2)R, S(CO)R, (SO.sub.2)OR, O(CO)OR, (CO)(CO)OR ##STR00236## CRNOH, CRNOR, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, amino, amino C1-C8 alkyl, aminocarbonyl C1-C8 alkyl, aminocarbonyloxy C1-C8 alkyl, aminothiocarbonyloxy C1-C8 alkyl, aminosulfonyl, or aminosulfonyloxy C1-C8 alkyl, wherein, the C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl is each independently unsubstituted or substituted by at least one group selected from halogen, cyano, hydroxyl, mercapto, carboxyl, OR, (CO)R, SR, (SO.sub.2)R, O(CO)H, O(CO)R, O(SO.sub.2)R, (CO)OR, O(CO)OR, O(CO)(CO)OH, O(CO)(CO)OR, O(C1-C8 alkyl)-(CO)OH, and O(C1-C8 alkyl)-(CO)OR; the C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl, or aryl C1-C8 alkyl is each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C8 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; the amino, amino C1-C8 alkyl, aminocarbonyl C1-C8 alkyl, aminocarbonyloxy C1-C8 alkyl, aminothiocarbonyloxy C1-C8 alkyl, aminosulfonyl, or aminosulfonyloxy C1-C8 alkyl is each independently unsubstituted or substituted by one or two groups selected from R.sub.11, OR.sub.11, (CO)R.sub.11, (CO)OR.sub.11, C1-C8 alkyl)-(CO)OR.sub.11, (SO.sub.2)R.sub.11, (SO.sub.2)OR.sub.11, C1-C8 alkyl)-(SO.sub.2)R.sub.11, (CO)N(R.sub.12).sub.2, and (SO.sub.2)N(R.sub.12).sub.2; R each independently represents hydrogen, halogen, C1-C8 alkoxy, C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, heterocyclyl, or heterocyclyl C1-C8 alkyl, wherein, the C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl is each independently unsubstituted or substituted by halogen; the C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, heterocyclyl, or heterocyclyl C1-C8 alkyl is each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C8 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; R each independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, aryl C2-C8 alkenyl, heterocyclyl, heterocyclyl C1-C8 alkyl, or heterocyclyl C2-C8 alkenyl, wherein, the C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl is each independently unsubstituted or substituted by at least one group selected from halogen, cyano, tri-C1-C8 alkylsilyl, OR.sub.13, SR.sub.13, O(CO)R.sub.13, (CO)R.sub.13, (CO)OR.sub.13, and O(CO)OR.sub.13; the C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, aryl C2-C8 alkenyl, heterocyclyl, heterocyclyl C1-C8 alkyl, or heterocyclyl C2-C8 alkenyl is each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C8 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; preferably, X.sub.1, X.sub.2, X.sub.3, and X.sub.4 each independently represent hydrogen, halogen, nitro, cyano, thiocyanato, hydroxyl, mercapto, sulfo, formyl, haloformyl, azido, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, PO(OR).sub.2, OR, (CO)R, SR, (SO)R, (SO.sub.2)R, Si(R).sub.3, O(CO)R, O(SO.sub.2)R, S(CO)R, (SO.sub.2)OR, O(CO)OR, (CO)(CO)OR, ##STR00237## CRNOH, CRNOR, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, amino, amino C1-C6 alkyl, aminocarbonyl C1-C6 alkyl, aminocarbonyloxy C1-C6 alkyl, aminothiocarbonyloxy C1-C6 alkyl, aminosulfonyl, or aminosulfonyloxy C1-C6 alkyl, wherein, the C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from halogen, cyano, hydroxyl, mercapto, carboxyl, OR, (CO)R, SR, (SO.sub.2)R, O(CO)H, O(CO)R, O(SO.sub.2)R, (CO)OR, O(CO)OR, O(CO)(CO)OH, O(CO)(CO)OR, O(C1-C6 alkyl)-(CO)OH, and O(C1-C6 alkyl)-(CO)OR; the C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl, or aryl C1-C6 alkyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C6 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; the amino, amino C1-C6 alkyl, aminocarbonyl C1-C6 alkyl, aminocarbonyloxy C1-C6 alkyl, aminothiocarbonyloxy C1-C6 alkyl, aminosulfonyl, or aminosulfonyloxy C1-C6 alkyl is each independently unsubstituted or substituted by one or two groups selected from R.sub.11, OR.sub.11, (CO)R.sub.11, (CO)OR.sub.11, C1-C6 alkyl)-(CO)OR.sub.11, (SO.sub.2)R.sub.11, (SO.sub.2)OR.sub.11, C1-C6 alkyl)-(SO.sub.2)R.sub.11, (CO)N(R.sub.12).sub.2, and (SO.sub.2)N(R.sub.12).sub.2; R each independently represents hydrogen, halogen, C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, heterocyclyl, or heterocyclyl C1-C6 alkyl, wherein, the C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl is each independently unsubstituted or substituted by halogen; the C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, heterocyclyl, or heterocyclyl C1-C6 alkyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C6 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; R each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, aryl C2-C6 alkenyl, heterocyclyl, heterocyclyl C1-C6 alkyl, or heterocyclyl C2-C6 alkenyl, wherein, the C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from halogen, cyano, tri-C1-C6 alkylsilyl, OR.sub.13, SR.sub.13, O(CO)R.sub.13, (CO)R.sub.13, (CO)OR.sub.13, and O(CO)OR.sub.13; the C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, aryl C2-C6 alkenyl, heterocyclyl, heterocyclyl C1-C6 alkyl, or heterocyclyl C2-C6 alkenyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C6 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; more preferably, X.sub.1, X.sub.2, X.sub.3, and X.sub.4 each independently represent hydrogen, halogen, nitro, cyano, thiocyanato, hydroxyl, mercapto, sulfo, formyl, haloformyl, azido, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, PO(OR).sub.2, OR, (CO)R, SR, (SO)R, (SO.sub.2)R, Si(R).sub.3, O(CO)R, O(SO.sub.2)R, S(CO)R, (SO.sub.2)OR, O(CO)OR, (CO)(CO)OR, ##STR00238## CRNOH, CRNOR, heterocyclyl, heterocyclyl C1-C3 alkyl, aryl, aryl C1-C3 alkyl, amino, amino C1-C3 alkyl, aminocarbonyl C1-C3 alkyl, aminocarbonyloxy C1-C3 alkyl, aminothiocarbonyloxy C1-C3 alkyl, aminosulfonyl, or aminosulfonyloxy C1-C3 alkyl, wherein, the C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from halogen, cyano, hydroxyl, mercapto, carboxyl, OR, (CO)R, SR, (SO.sub.2)R, O(CO)H, O(CO)R, O(SO.sub.2)R, (CO)OR, O(CO)OR, O(CO)(CO)OH, O(CO)(CO)OR, O(C1-C3 alkyl)-(CO)OH, and O(C1-C3 alkyl)-(CO)OR; the C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclyl, heterocyclyl C1-C3 alkyl, aryl, or aryl C1-C3 alkyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C3 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; the amino, amino C1-C3 alkyl, aminocarbonyl C1-C3 alkyl, aminocarbonyloxy C1-C3 alkyl, aminothiocarbonyloxy C1-C3 alkyl, aminosulfonyl, or aminosulfonyloxy C1-C3 alkyl is each independently unsubstituted or substituted by one or two groups selected from R.sub.11, OR.sub.11, (CO)R.sub.11, (CO)OR.sub.11, C1-C3 alkyl)-(CO)OR.sub.11, (SO.sub.2)R.sub.11, (SO.sub.2)OR.sub.11, C1-C3 alkyl)-(SO.sub.2)R.sub.11, (CO)N(R.sub.12).sub.2, and (SO.sub.2)N(R.sub.12).sub.2; R each independently represents hydrogen, halogen, C1-C6 alkoxy, C1-C6 alkoxy C1-C3 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, aryl, aryl C1-C3 alkyl, heterocyclyl, or heterocyclyl C1-C3 alkyl, wherein, the C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl is each independently unsubstituted or substituted by halogen; the C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, aryl, aryl C1-C3 alkyl, heterocyclyl, or heterocyclyl C1-C3 alkyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C3 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; R each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, aryl, aryl C1-C3 alkyl, aryl C2-C3 alkenyl, heterocyclyl, heterocyclyl C1-C3 alkyl, or heterocyclyl C2-C3 alkenyl, wherein, the C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from halogen, cyano, tri-C1-C6 alkylsilyl, OR.sub.13, SR.sub.13, O(CO)R.sub.13, (CO)R.sub.13, (CO)OR.sub.13, and O(CO)OR.sub.13; the C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, aryl, aryl C1-C3 alkyl, aryl C2-C3 alkenyl, heterocyclyl, heterocyclyl C1-C3 alkyl, or heterocyclyl C2-C3 alkenyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C3 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen.

5. The heterocycle-substituted aromatic compound according to claim 1, wherein it is characterized in that, W.sub.3 each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, ##STR00239## wherein, the C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl is each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, C3-C8 cycloalkyl, tri-C1-C8 alkylsilyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, ##STR00240## the C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, or aryl is each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C8 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; W.sub.4 and W.sub.5 each independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, ##STR00241## wherein, the C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl is each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, C3-C8 cycloalkyl, tri-C1-C8 alkylsilyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, ##STR00242## the C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, or aryl is each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C8 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; or NW.sub.4W.sub.5 represents ##STR00243## which is unsubstituted or substituted by at least one group selected from oxo, C1-C8 alkyl, and C1-C8 alkoxycarbonyl; X.sub.11 each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl, or aryl C1-C8 alkyl, wherein, the C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl, or aryl C1-C8 alkyl is each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C8 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; X.sub.12 each independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl, or aryl C1-C8 alkyl, wherein, the C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl, heterocyclyl C1-C8 alkyl, aryl, or aryl C1-C8 alkyl is each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C8 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; X.sub.13 and X.sub.14 each independently represent hydrogen, halogen, cyano, C1-C8 alkoxy, C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkylsulfonyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, heterocyclyl, or heterocyclyl C1-C8 alkyl, or the group CX.sub.13X.sub.14 together forms a 5-8 membered carbocycle or oxygen-, sulfur-, or nitrogen-containing heterocycle, or the group NX.sub.13X.sub.14 together forms ##STR00244## wherein, the C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl is each independently unsubstituted or substituted by halogen; the C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, heterocyclyl, or heterocyclyl C1-C8 alkyl is each independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, halo C3-C8 cycloalkyl, C1-C8 alkyl-substituted C3-C8 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C8 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; the 5-8 membered carbocycle or oxygen-, sulfur-, or nitrogen-containing heterocycle is unsubstituted or substituted by at least one group selected from C1-C8 alkyl, C1-C8 alkoxycarbonyl, and benzyl, or forms a fused ring structure with aryl or heterocyclyl; the ##STR00245## is unsubstituted or substituted by at least one group selected from oxo, C1-C8 alkyl, and C1-C8 alkoxycarbonyl; preferably, W.sub.3 each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, ##STR00246## wherein, the C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from halogen, cyano, nitro, C3-C6 cycloalkyl, tri-C1-C6 alkylsilyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, ##STR00247## the C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, or aryl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C6 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; W.sub.4 and W.sub.5 each independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, ##STR00248## wherein, the C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from halogen, cyano, nitro, C3-C6 cycloalkyl, tri-C1-C6 alkylsilyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, ##STR00249## the C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, or aryl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C6 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; or NW.sub.4W.sub.5 represents ##STR00250## which is unsubstituted or substituted by 1, 2, or 3 groups selected from oxo, C1-C6 alkyl, and C1-C6 alkoxycarbonyl; X.sub.11 each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl, or aryl C1-C6 alkyl, wherein, the C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl, or aryl C1-C6 alkyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C6 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; X.sub.12 each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl, or aryl C1-C6 alkyl, wherein, the C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl, heterocyclyl C1-C6 alkyl, aryl, or aryl C1-C6 alkyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C6 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; X.sub.13 and X.sub.14 each independently represent hydrogen, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfonyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, heterocyclyl, or heterocyclyl C1-C6 alkyl, or the group CX.sub.13X.sub.14 together forms a 5-8 membered saturated carbocycle, ##STR00251## or the group NX.sub.13X.sub.14 together forms ##STR00252## wherein, the C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl is each independently unsubstituted or substituted by halogen; the C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, heterocyclyl, or heterocyclyl C1-C6 alkyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C6 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; the 5-8 membered saturated carbocycle, ##STR00253## is unsubstituted or substituted by 1, 2, or 3 groups selected from C1-C6 alkyl, C1-C6 alkoxycarbonyl, and benzyl, or forms a fused ring with aryl or heterocyclyl; the, ##STR00254## is unsubstituted or substituted by 1, 2, or 3 groups selected from oxo, C1-C6 alkyl, and C1-C6 alkoxycarbonyl; more preferably, W.sub.3 each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, ##STR00255## wherein, the C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from halogen, cyano, nitro, C3-C6 cycloalkyl, tri-C1-C6 alkylsilyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, ##STR00256## the C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, or aryl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3C6 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C3 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; W.sub.4 and W.sub.5 each independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, ##STR00257## wherein, the C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from halogen, cyano, nitro, C3-C6 cycloalkyl, tri-C1-C6 alkylsilyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, ##STR00258## the C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, or aryl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C3 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; or NW.sub.4W.sub.5 represents ##STR00259## which is unsubstituted or substituted by 1, 2, or 3 groups selected from oxo, C1-C6 alkyl, and C1-C6 alkoxycarbonyl; X.sub.11 each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclyl, heterocyclyl C1-C3 alkyl, aryl, or aryl C1-C3 alkyl, wherein, the C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclyl, heterocyclyl C1-C3 alkyl, aryl, or aryl C1-C3 alkyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C3 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; X.sub.12 each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclyl, heterocyclyl C1-C3 alkyl, aryl, or aryl C1-C3 alkyl, wherein, the C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclyl, heterocyclyl C1-C3 alkyl, aryl, or aryl C1-C3 alkyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3-C6 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C3 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; X.sub.13 and X.sub.14 each independently represent hydrogen, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxy C1-C3 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfonyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, aryl, aryl C1-C3 alkyl, heterocyclyl, or heterocyclyl C1-C3 alkyl, or the group CX.sub.13X.sub.14 together forms a 5-8 membered saturated carbocycle, ##STR00260## or the group NX.sub.13X.sub.14 together forms ##STR00261## wherein, the C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl is each independently unsubstituted or substituted by halogen; the C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, aryl, aryl C1-C3 alkyl, heterocyclyl, or heterocyclyl C1-C3 alkyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, halo C3-C6 cycloalkyl, C1-C6 alkyl-substituted C3C6 cycloalkyl, OR.sub.14, SR.sub.14, (CO)OR.sub.14, (SO.sub.2)R.sub.14, N(R.sub.14).sub.2, and O(C1-C3 alkyl)-(CO)OR.sub.14, or two adjacent carbon atoms on the ring form a fused ring with OCH.sub.2CH.sub.2 or OCH.sub.2O that is unsubstituted or substituted by halogen; the 5-8 membered saturated carbocycle, ##STR00262## is unsubstituted or substituted by 1, 2, or 3 groups selected from C1-C6 alkyl, C1-C6 alkoxycarbonyl, and benzyl, or forms a fused ring with phenyl or thienyl; the ##STR00263## is unsubstituted or substituted by 1, 2, or 3 groups selected from oxo, C1-C6 alkyl, and C1-C6 alkoxycarbonyl.

6. The heterocycle-substituted aromatic compound according to claim 1, wherein it is characterized in that, R.sub.11 each independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, phenyl, or benzyl, wherein, the C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl is each independently unsubstituted or substituted by halogen; the phenyl or benzyl is each independently unsubstituted or substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylsulfanyl, C1-C8 alkylsulfonyl, C1-C8 alkoxy, and halo C1-C8 alkoxy; R.sub.12 each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylsulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, or C3-C8 cycloalkenyl C1-C8 alkyl, or the group N(R.sub.12).sub.2 in (CO)N(R.sub.12).sub.2 or (SO.sub.2)N(R.sub.12).sub.2 each independently represents ##STR00264## which is unsubstituted or substituted by at least one group selected from oxo, C1-C8 alkyl, and C1-C8 alkoxycarbonyl; R.sub.13 each independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, phenyl, or phenyl that is substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, C1-C8 alkoxy, halo C1-C8 alkoxy, C1-C8 alkoxycarbonyl, C1-C8 alkylsulfanyl, C1-C8 alkylsulfonyl, and phenoxy that is substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, C1-C8 alkoxy, and halo C1-C8 alkoxy; R.sub.14 each independently represents hydrogen, C1-C8 alkyl, halo C1-C8 alkyl, phenyl, or phenyl that is substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylsulfanyl, C1-C8 alkylsulfonyl, C1-C8 alkoxy, and halo C1-C8 alkoxy; preferably, R.sub.11 each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, phenyl, or benzyl, wherein, the C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl is each independently unsubstituted or substituted by halogen; the phenyl or benzyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfonyl, C1-C6 alkoxy, and halo C1-C6 alkoxy; R.sub.12 each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, or C3-C6 cycloalkenyl C1-C6 alkyl, or the group N(R.sub.12).sub.2 in (CO N(R.sub.12).sub.2 or (SO.sub.2)N(R.sub.12).sub.2 each independently represents ##STR00265## which is unsubstituted or substituted by 1, 2, or 3 groups selected from oxo, C1-C6 alkyl, and C1-C6 alkoxycarbonyl; R.sub.13 each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, phenyl, or phenyl that is substituted by 1, 2, or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxy, halo C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfonyl, and phenoxy that is substituted by 1, 2, or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxy, and halo C1-C6 alkoxy; R.sub.14 each independently represents hydrogen, C1-C6 alkyl, halo C1-C6 alkyl, phenyl, or phenyl that is substituted by 1, 2, or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfonyl, C1-C6 alkoxy, and halo C1-C6 alkoxy; more preferably, R.sub.11 each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, phenyl, or benzyl, wherein, the C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl is each independently unsubstituted or substituted by halogen; the phenyl or benzyl is each independently unsubstituted or substituted by 1, 2, or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfonyl, C1-C6 alkoxy, and halo C1-C6 alkoxy; R.sub.12 each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, or C3-C6 cycloalkenyl C1-C3 alkyl, or the group N(R.sub.12).sub.2 in (CO)N(R.sub.12).sub.2 or (SO.sub.2)N(R.sub.12).sub.2 each independently represents ##STR00266## which is unsubstituted or substituted by 1, 2, or 3 groups selected from oxo, C1-C6 alkyl, and C1-C6 alkoxycarbonyl; R.sub.13 each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, phenyl, or phenyl that is substituted by 1, 2, or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxy, halo C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfonyl, and phenoxy that is substituted by 1, 2, or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxy, and halo C1-C6 alkoxy; R.sub.14 each independently represents hydrogen, C1-C6 alkyl, halo C1-C6 alkyl, phenyl, or phenyl that is substituted by 1, 2, or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfonyl, C1-C6 alkoxy, and halo C1-C6 alkoxy; further preferably, the compound is selected from any one in Table 1.

7. A method for preparing the heterocycle-substituted aromatic compound according claim 1, wherein it is characterized in that it comprises the following steps: subjecting the compound shown in the general formula II and the compound shown in the general formula III to reaction to prepare the compound as shown in the general formula I, and the chemical reaction equation is as follows: ##STR00267## wherein, Hal represents halogen; the definitions of substituents X.sub.1, X.sub.2, R.sub.1, R.sub.2, R.sub.3, R.sub.4, M, M.sub.2, Q, Y, and Z are as described in claim 1; preferably, the reaction is carried out in the presence of a base and a solvent; more preferably, the base is selected from at least one of nitrogen-containing bases; the solvent is selected from at least one of aromatic hydrocarbons, THF, DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, dioxane, dichloromethane, toluene, and ethyl acetate.

8. A herbicidal composition, wherein it is characterized in that it comprises a herbicidally effective amount of at least one of the heterocycle-substituted aromatic compound according to claim 1, preferably, also comprising a formulation auxiliary.

9. A method for controlling a weed, wherein it is characterized in that it comprises applying a herbicidally effective amount of at least one of the heterocycle-substituted aromatic compound according to claim 1 to a plant or a weedy area.

10. A method for preventing and controlling a weed among a useful crop, comprising applying a herbicidally effective amount of at least one of the heterocycle-substituted aromatic compound according to claim 1.

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

12. The method according to claim 10, wherein the useful crop is a transgenic crop or a crop treated by a genome editing technique.

13. A method for preventing and controlling a weed among a useful crop, comprising applying a herbicidally effective amount of the herbicidal composition according to claim 8.

14. The method according to claim 13, wherein the useful crop is a transgenic crop or a crop treated by a genome editing technique.

Description

DETAILED EMBODIMENTS OF THE INVENTION

[0134] The following examples are used to illustrate the present invention and should not be construed as limiting the present invention in any way. The scope of rights claimed by the present invention is described in the Claims.

[0135] In view of the economy and diversity of the compounds, some compounds were preferably synthesized. Among the many synthesized compounds, selected ones are listed in Table 1 below. The specific compound structures and corresponding compound information are as set forth in Tables 1-2. The compounds in Table 1 are only to better illustrate the present invention but do not limit the present invention. For a person skilled in the art, it should not be understood that the scope of the above-mentioned subject matters of the present invention is limited to the following compounds.

TABLE-US-00001 TABLE 1 Compound structure I [00049] embedded image No. X.sub.1 X.sub.2 Y Z Q M.sub.1 M.sub.2 R.sub.1 R.sub.2 R.sub.3 R.sub.4 1 CH.sub.3 [00050] Cl F CH.sub.2 CH N Cl CH.sub.3 CF.sub.3 H 2 CH.sub.3 [00051] Cl F CH.sub.2 N CH Cl H CF.sub.3 H 3 CH.sub.3 [00052] Cl F CH.sub.2 N N Cl H CF.sub.3 H 4 CH.sub.3 [00053] Cl F CH.sub.2 N N.sup.+O.sup. Cl H CF.sub.3 H 5 CH.sub.3 [00054] embedded image Cl OH CH.sub.2 CH N Cl H CF.sub.3 H 6 CH.sub.3 [00055] CN H CH.sub.2 CH N Cl H CF.sub.3 H 7 CH.sub.3 [00056] NO.sub.2 F CH.sub.2 CH N Cl H CF.sub.3 H 8 CH.sub.3 [00057] NH.sub.2 F CH.sub.2 CH N Cl H CF.sub.3 H 9 CH.sub.3 [00058] CF.sub.3 F CH.sub.2 CH N Cl H CF.sub.3 H 10 CH.sub.3 [00059] embedded image Br F CH.sub.2 CH N Cl H CF.sub.3 H 11 CH.sub.3 [00060] CN F CH.sub.2 CH N Cl H CF.sub.3 H 12 [00061] [00062] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 13 [00063] [00064] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 14 [00065] [00066] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 15 [00067] [00068] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 16 F [00069] embedded image Cl F CH.sub.2 CH N Cl H CF.sub.3 H 17 Cl [00070] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 18 [00071] [00072] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 19 CF.sub.3 [00073] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 20 CH.sub.2Br [00074] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 21 OH [00075] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 22 OCH.sub.3 [00076] embedded image Cl F CH.sub.2 CH N Cl H CF.sub.3 H 23 OCH.sub.2CH.sub.3 [00077] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 24 CH.sub.2OH [00078] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 25 CH.sub.2OCH.sub.3 [00079] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 26 SCH.sub.3 [00080] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 27 [00081] embedded image [00082] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 28 NH.sub.2 [00083] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 29 NHCH.sub.3 [00084] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 30 N(CH.sub.3).sub.2 [00085] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 31 CN [00086] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 32 CH.sub.2CN [00087] embedded image Cl F CH.sub.2 CH N Cl H CF.sub.3 H 33 [00088] [00089] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 34 [00090] [00091] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 35 [00092] [00093] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 36 [00094] [00095] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 37 [00096] [00097] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 38 CH.sub.3 [00098] embedded image Cl F CH.sub.2 CH N Cl H CF.sub.3 H 39 CH.sub.3 [00099] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 40 CH.sub.3 [00100] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 41 CH.sub.3 [00101] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 42 CH.sub.3 [00102] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 43 CH.sub.3 [00103] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 44 CH.sub.3 [00104] embedded image Cl F CH.sub.2 CH N Cl H CF.sub.3 H 45 CH.sub.3 [00105] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 46 CH.sub.3 [00106] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 47 CH.sub.3 [00107] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 48 CH.sub.3 [00108] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 49 CH.sub.3 [00109] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 50 CH.sub.3 [00110] embedded image Cl F CH.sub.2 CH N Cl H CF.sub.3 H 51 CH.sub.3 [00111] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 52 CH.sub.3 [00112] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 53 CH.sub.3 [00113] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 54 CH.sub.3 [00114] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 55 CH.sub.3 [00115] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 56 CH.sub.3 [00116] embedded image Cl F CH.sub.2 CH N Cl H CF.sub.3 H 57 CH.sub.3 [00117] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 58 CH.sub.3 [00118] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 59 CH.sub.3 [00119] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 60 CH.sub.3 [00120] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 61 CH.sub.3 [00121] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 62 CH.sub.3 [00122] embedded image Cl F CH.sub.2 CH N Cl H CF.sub.3 H 63 CH.sub.3 [00123] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 64 CH.sub.3 [00124] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 65 CH.sub.3 [00125] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 66 CH.sub.3 [00126] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 67 CH.sub.3 [00127] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 68 CH.sub.3 [00128] embedded image Cl F CH.sub.2 CH N Cl H CF.sub.3 H 69 CH.sub.3 [00129] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 70 CH.sub.3 [00130] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 71 CH.sub.3 [00131] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 72 CH.sub.3 [00132] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 73 CH.sub.3 [00133] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 74 CH.sub.3 [00134] embedded image Cl F CH.sub.2 CH N Cl H CF.sub.3 H 75 CH.sub.3 [00135] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 76 CH.sub.3 [00136] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 77 CH.sub.3 [00137] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 78 CH.sub.3 [00138] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 79 CH.sub.3 [00139] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 80 CH.sub.3 [00140] embedded image Cl F CH.sub.2 CH N Cl H CF.sub.3 H 81 CH.sub.3 [00141] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 82 CH.sub.3 [00142] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 83 CH.sub.3 [00143] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 84 CH.sub.3 [00144] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 85 CH.sub.3 [00145] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 86 CH.sub.3 [00146] embedded image Cl F CH.sub.2 CH N Cl H CF.sub.3 H 87 CH.sub.3 [00147] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 88 CH.sub.3 [00148] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 89 CH.sub.3 [00149] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 90 CH.sub.3 [00150] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 91 CH.sub.3 [00151] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 92 CH.sub.3 [00152] embedded image Cl F CH.sub.2 CH N Cl H CF.sub.3 H 93 CH.sub.3 [00153] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 94 CH.sub.3 [00154] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 95 CH.sub.3 [00155] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 96 CH.sub.3 [00156] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 97 CH.sub.3 [00157] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 98 CH.sub.3 [00158] embedded image Cl F CH.sub.2 CH N Cl H CF.sub.3 H 99 CH.sub.3 [00159] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 100 CH.sub.3 [00160] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 101 CH.sub.3 [00161] Cl F CH.sub.2 CH N Cl H CF.sub.3 CH.sub.3 102 CH.sub.3 [00162] Cl F CH.sub.2 CH N Cl H OCH.sub.3 H 103 CH.sub.3 [00163] embedded image Cl F CH.sub.2 CH N Cl H SCH.sub.3 H 104 CH.sub.3 [00164] Cl F CH.sub.2 CH N Cl H [00165] H 105 H [00166] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 106 CH.sub.3 [00167] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 107 CH.sub.3 [00168] Cl F CH.sub.2 CH CH Cl H CF.sub.3 H 108 CH.sub.3 [00169] Cl F CH.sub.2 N CH Cl H CF.sub.3 H 109 CH.sub.3 [00170] embedded image Cl F CH.sub.2 N N Cl H CF.sub.3 H 110 CH.sub.3 [00171] Cl F CH.sub.2 CH N.sup.+O.sup. Cl H CF.sub.3 H 111 CH.sub.3 [00172] Cl F CH(CH.sub.3) CH N Cl H CF.sub.3 H 112 CH.sub.3 [00173] Cl F CH.sub.2 CH N Cl H H H 113 CH.sub.3 [00174] Cl F CH.sub.2 CH N Cl H [00175] H 114 CH.sub.3 [00176] embedded image Cl F CH.sub.2 CH N Cl H [00177] H 115 CH.sub.3 [00178] Cl F CH.sub.2 CH N Cl H F H 116 CH.sub.3 [00179] Cl F CH.sub.2 CH N Cl H Cl H 117 CH.sub.3 [00180] Cl F CH.sub.2 CH N Cl H Br H 118 CH.sub.3 [00181] Cl F CH.sub.2 CH N Cl H [00182] H 119 CH.sub.3 [00183] Cl F CH.sub.2 CH N Cl H [00184] embedded image H 120 CH.sub.3 [00185] Cl F CH.sub.2 CH N Cl H [00186] H 121 CH.sub.3 [00187] Cl F CH.sub.2 CH N Cl H OCH.sub.3 H 122 CH.sub.3 [00188] Cl F CH.sub.2 CH N Cl H [00189] H 123 CH.sub.3 [00190] Cl F CH.sub.2 CH N Cl H [00191] H 124 CH.sub.3 [00192] Cl F CH.sub.2 CH N Cl H CN H 125 CH.sub.3 [00193] embedded image Cl F CH.sub.2 CH N Cl H NO.sub.2 H 126 H [00194] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 127 CF.sub.3 [00195] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 128 [00196] [00197] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 129 [00198] [00199] Cl F CH.sub.2 CH N Cl H CF.sub.3 H 130 CH.sub.3 [00200] Cl F CH.sub.2 CH N F H CF.sub.3 H 131 CH.sub.3 [00201] embedded image Cl F CH.sub.2 CH N F F [00202] H 132 CH.sub.3 [00203] Cl F CH.sub.2 CH N F H F H 133 CH.sub.3 [00204] Cl F CH.sub.2 CH N F H Cl H 134 CH.sub.3 [00205] Cl F CH.sub.2 CH N F H CH.sub.3 H 135 CH.sub.3 [00206] Cl F CH.sub.2 CH N H H CF.sub.3 H 136 CH.sub.3 [00207] Cl F CH.sub.2 CH N CH.sub.3 H CF.sub.3 H 137 CH.sub.3 [00208] embedded image Cl F CH.sub.2 CH N [00209] H CF.sub.3 H 138 CH.sub.3 [00210] Cl F CH.sub.2 CH N OCH.sub.3 H CF.sub.3 H 139 CH.sub.3 [00211] CF.sub.3 F CH.sub.2 CH N Cl H CF.sub.3 H 140 CH.sub.3 [00212] CN F CH.sub.2 CH N Cl H CF.sub.3 H 141 CH.sub.3 [00213] Cl F CH.sub.2 CH N Cl H CF.sub.3 H

TABLE-US-00002 TABLE 2 .sup.1H NMR of Compounds No. .sup.1H NMR 1 .sup.1H NMR (300 MHz, Chloroform-d) 8.78 (s, 1H), 7.79 (d, J = 7.5 Hz, 1H), 7.31 (d, J = 9.0 Hz, 1H), 4.27 (q, J = 7.0 Hz, 2H), 4.00 (d, J = 17.5 Hz, 1H), 3.40 (d, J = 17.5 Hz, 1H), 2.62 (s, 3H), 1.72 (s, 3H), 1.32 (t, J = 7.0 Hz, 3H). 10 .sup.1H NMR (300 MHz, Chloroform-d) 8.85 (s, 1H), 8.07 (s, 1H), 7.72 (d, J = 7.2 Hz, 1H), 7.52 (d, J = 8.7 Hz, 1H), 4.01 (d, J = 17.4 Hz, 1H), 3.83 (q, J = 7.2 Hz, 2H), 3.43 (d, J = 17.4 Hz, 1H), 1.74 (s, 3H), 1.26 (t, J = 7.2 Hz, 3H). 12 .sup.1H NMR (300 MHz, DMSO-d.sub.6) 9.09 (s, 1H), 8.68 (s, 1H), 7.88-7.81 (m, 2H), 4.18 (q, J = 6.9 Hz, 2H), 3.79 (d, J = 18.0 Hz, 1H), 3.58 (d, J = 18.0 Hz, 1H), 2.33-2.23 (m, 1H), 1.21 (t, J = 6.9 Hz, 3H), 0.91-0.85 (m, 6H). 15 .sup.1H NMR (300 MHz, Chloroform-d) 8.85 (s, 1H), 8.07 (s, 1H), 7.56 (d, J = 7.0 Hz, 1H), 7.36 (d, J = 9.0 Hz, 1H), 5.14- 5.12 (m, 1H), 4.18 (q, J = 7.0 Hz, 2H), 3.60-3.58 (m, 1H), 1.39-1.30 (m, 4H), 0.88-0.56 (m, 4H). 43 .sup.1H NMR (300 MHz, DMSO-d.sub.6) 9.10 (m, 1H), 8.70 (s, 1H), 7.85 (d, J = 9.0 Hz, 1H), 7.82 (d, J = 7.0 Hz, 1H), 5.19-5.08 (m, 1H), 3.92-3.82 (m, 1H), 3.52-3.45 (m, 1H), 1.85-1.59 (m, 8H), 1.56 (s, 3H). 44 .sup.1H NMR (300 MHz, Chloroform-d) 8.86 (s, 1H), 8.07 (s, 1H), 7.83 (d, J = 7.5 Hz, 1H), 7.32 (d, J = 9.0 Hz, 1H), 4.80- 4.70 (m, 1H), 4.60-4.52 (m, 1H), 4.53-4.47 (m, 1H), 4.45-4.36 (m, 1H), 4.02 (d, J = 17.5 Hz, 1H), 3.44 (d, J = 17.5 Hz, 1H), 1.75 (s, 3H). 45 .sup.1H NMR (300 MHz, Chloroform-d) 8.85 (s, 1H), 8.07 (s, 1H), 7.83 (d, J = 7.5 Hz, 1H), 7.33 (d, J = 9.0 Hz, 1H), 4.62- 4.50 (m, 2H), 4.02 (d, J = 17.5 Hz, 1H), 3.50 (d, J = 17.5 Hz, 1H), 1.78 (s, 3H). 49 .sup.1H NMR (300 MHz, CDCl.sub.3) 8.87 (s, 1H), 8.06 (s, 1H), 7.82 (d, J = 7.0 Hz, 1H), 7.31 (d, J = 9.0 Hz, 1H), 5.36-5.31 (m, 2H), 4.04 (d, J = 17.5 Hz, 1H), 3.49-3.46 (m, 3H), 3.42 (d, J = 17.5 Hz, 1H), 1.74 (s, 3H). 50 .sup.1H NMR (300 MHz, CDCl.sub.3) 8.86 (d, J = 0.7 Hz, 1H), 8.07 (d, J = 1.9 Hz, 1H), 7.84 (d, J = 7.4 Hz, 1H), 7.33 (d, J = 9.1 Hz, 1H), 5.27 (d, J = 1.8 Hz, 2H), 4.04 (d, J = 17.4 Hz, 1H), 3.43 (d, J = 17.4 Hz, 1H), 2.26 (s, 3H), 1.75 (s, 4H). 51 .sup.1H NMR (300 MHz, DMSO-d.sub.6) 9.10 (s, 1H), 8.70 (s, 1H), 7.87 (d, J = 7.5 Hz, 1H), 7.32 (d, J = 9.0 Hz, 1H), 5.58-5.52 (m, 1H), 3.99-3.90 (m, 1H), 3.60-3.55 (m, 1H), 1.63 (s, 3H), 1.58 (d, J = 7.0 Hz, 3H). 65 .sup.1H NMR (300 MHz, Chloroform-d) 8.85 (s, 1H), 8.06 (s, 1H), 7.81 (d, J = 7.5 Hz, 1H), 7.32 (d, J = 9.0 Hz, 1H), 4.11 (d, J = 17.5 Hz, 1H), 3.45 (d, J = 17.5 Hz, 1H), 2.06 (d, J = 5.5 Hz, 6H), 1.80 (s, 3H). 67 .sup.1H NMR (300 MHz, Chloroform-d) 8.85 (s, 1H), 8.07 (s, 1H), 7.82 (d, J = 7.2 Hz, 1H), 7.34 (d, J = 9.0 Hz, 1H), 4.14 (d, J = 17.4 Hz, 1H), 3.50 (d, J = 17.4 Hz, 1H), 2.23 (s, 3H), 1.84 (s, 3H). 68 .sup.1H NMR (300 MHz, Chloroform-d) 8.85 (s, 1H), 8.07 (s, 1H), 7.82 (d, J = 7.5 Hz, 1H), 7.33 (d, J = 9.0 Hz, 1H), 4.17- 4.05 (m, 3H), 3.47 (d, J = 17.4 Hz, 1H), 3.35 (s, 3H), 2.09 (s, 3H), 1.81 (s, 3H). 69 .sup.1H NMR (300 MHz, Chloroform-d) 8.85 (s, 1H), 8.06 (s, 1H), 7.81 (d, J = 7.2 Hz, 1H), 7.32 (d, J = 9.0 Hz, 1H), 4.20 (q, J = 7.2 Hz, 2H), 4.10 (d, J = 17.4 Hz, 1H), 3.44 (d, J = 17.4 Hz, 1H), 2.07 (s, 3H), 1.79 (s, 3H), 1.32 (t, J = 7.2 Hz, 3H). 70 .sup.1H NMR (300 MHz, Chloroform-d) 8.79 (s, 1H), 8.01 (s, 1H), 7.83-7.69 (m, 1H), 7.36-7.22 (m, 1H), 4.36-4.20 (m, 2H), 4.41-3.90 (m, 1H), 3.53-3.33 (m, 1H), 2.25-2.01 (m, 3H), 1.82-1.64 (m, 3H), 1.34-1.25 (m, 3H). 71 .sup.1H NMR (300 MHz, Chloroform-d) 8.87 (s, 1H), 8.08 (s, 1H), 7.71 (d, J = 7.2 Hz, 1H), 7.59 (d, J = 9.0 Hz, 1H), 7.46- 7.30 (m, 10H), 3.86 (d, J = 17.4 Hz, 1H), 3.34 (d, J = 17.4 Hz, 1H), 1.62 (s, 3H). 72 .sup.1H NMR (300 MHz, Chloroform-d) 8.85 (s, 1H), 8.34 (s, 1H), 8.06 (s, 1H), 7.86-7.74 (m, 1H), 7.58 (d, J = 2.4 Hz, 1H), 7.37-7.24 (m, 1H), 6.95-6.93 (m, 1H), 6.53-6.50 (m, 1H), 4.14 (d, J = 17.4 Hz, 1H), 3.51 (d, J = 17.4 Hz, 1H), 1.81 (s, 3H). 73 .sup.1H NMR (300 MHz, Chloroform-d) 8.86 (s, 1H), 8.34 (s, 1H), 8.06 (s, 1H), 7.82 (d, J = 7.2 Hz, 1H), 7.31 (d, J = 9.0, 1H), 6.95-6.83 (m, 2H), 4.12 (d, J = 17.4 Hz, 1H), 3.49 (d, J = 17.4 Hz, 1H), 2.35 (s, 3H), 1.81 (s, 3H). 74 .sup.1H NMR (300 MHz, Chloroform-d) 8.85 (s, 1H), 8.06 (s, 1H), 7.82 (d, J = 7.2 Hz, 1H), 7.32 (d, J = 9.0 Hz, 1H), 4.11 (d, J = 17.4 Hz, 1H), 3.45 (d, J = 17.4 Hz, 1H), 2.64-2.55 (m, 4H), 1.84-1.80 (m, 4H), 1.78 (s, 3H). 76 .sup.1H NMR (300 MHz, DMSO-d.sub.6) 9.10 (s, 1H), 8.70 (s, 1H), 7.83 (s, 1H), 7.80 (d, J = 3.0 Hz, 1H), 4.06-3.99 (m, 2H), 3.37 (d, J = 17.7 Hz, 1H), 3.21 (d, J = 17.7 Hz, 1H), 2.41-2.31 (m, 2H), 1.95-1.90 (m, 2H), 1.36 (s, 3H), 1.14 (t, J = 9.0 Hz, 3H). 78 .sup.1H NMR (300 MHz, CDCl.sub.3) 8.85 (s, 1H), 8.06 (s, 1H), 7.83 (d, J = 7.5 Hz, 1H), 7.31 (d, J = 9.0 Hz, 1H), 3.86 (d, J = 17.5 Hz, 1H), 3.44 (d, J = 17.5 Hz, 1H), 2.85 (dd, J = 7.5 Hz, 2H), 1.71 (s, 3H), 1.23 (d, J = 7.5 Hz, 3H). 97 .sup.1H NMR (300 MHz, CDCl.sub.3) 8.85 (s, 1H), 8.06 (s, 1H), 7.83 (d, J = 7.5 Hz, 1H), 7.31 (d, J = 9.0 Hz, 1H), 5.97 (s, 1H), 4.16 (d, J = 18.0 Hz, 1H), 3.71 (d, J = 18.0 Hz, 1H), 2.55 (s, 3H), 2.22 (s, 3H), 1.96 (s, 3H). 102 .sup.1H NMR (300 MHz, Chloroform-d) 8.30 (d, J = 2.7 Hz, 1H), 7.77 (d, J = 7.5 Hz, 1H), 7.33 (d, J = 2.7 Hz, 1H), 7.27 (d, J = 8.7 Hz, 1H), 4.26 (q, J = 6.9 Hz, 2H), 3.99 (d, J = 17.7 Hz, 1H), 3.91 (s, 3H), 3.39 (d, J = 17.7 Hz, 1H), 1.71 (s, 3H), 1.32 (t, J = 6.9 Hz, 3H). 104 .sup.1H NMR (300 MHz, Chloroform-d) 8.68 (d, J = 2.1 Hz, 1H), 7.84 (d, J = 2.1 Hz, 1H), 7.81 (d, J = 7.5, Hz, 1H), 7.29 (d, J = 9.3 Hz, 1H), 5.53 (d, J = 1.8 Hz, 1H), 5.29 (d, J = 1.8 Hz, 1H), 5.26 (s, 2H), 4.02 (d, J = 17.4 Hz, 1H), 3.42 (d, J = 17.4 Hz, 1H), 2.26 (s, 3H), 2.19 (s, 3H), 1.74 (s, 3H). 105 .sup.1H NMR (300 MHz, Chloroform-d) 8.86 (s, 1H), 8.07 (s, 1H), 7.85 (d, J = 7.2 Hz, 1H), 7.34 (d, J = 9.0 Hz, 1H), 5.29- 5.17 (m, 1H), 4.39 (t, J = 6.9 Hz, 2H), 3.89-3.76 (m, 2H), 2.78 (t, J = 6.9 Hz, 2H), 2.16 (s, 3H). 111 .sup.1H NMR (300 MHz, DMSO-d.sub.6) 9.09 (s, 1H), 8.70 (s, 1H), 7.89-7.77 (m, 2H), 4.20-4.13 (m, 1H), 2.07-2.06 (m, 3H), 2.01-2.00 (m, 3H), 1.47 (s, 3H), 1.01 (d, J = 7.5 Hz, 3H). 113 .sup.1H NMR (300 MHz, Chloroform-d) 8.67 (d, J = 2.1 Hz, 1H), 7.84 (d, J = 2.1 Hz, 1H), 7.79 (d, J = 7.5 Hz, 1H), 7.29 (d, J = 9.3 Hz, 1H), 5.52 (d, J = 1.8 Hz, 1H), 5.29 (d, J = 1.8 Hz, 1H), 4.10 (d, J = 17.7 Hz, 1H), 3.44 (d, J = 17.7 Hz, 1H), 2.19- 2.17 (t, J = 2.4 Hz, 3H), 2.07 (s, 3H), 2.05 (s, 3H), 1.79 (s, 3H). 127 .sup.1H NMR (300 MHz, Chloroform-d) 8.87 (s, 1H), 8.08 (s, 1H), 7.84 (d, J = 7.2 Hz, 1H), 7.37 (d, J = 9.0 Hz, 1H), 4.34 (d, J = 18.3 Hz, 1H), 4.01 (d, J = 18.3 Hz, 1H), 2.10 (d, J = 3.0 Hz, 6H). 129 .sup.1H NMR (300 MHz, Chloroform-d) 8.79 (s, 1H), 8.00 (s, 1H), 7.70 (d, J = 7.5 Hz, 1H), 7.26 (d, J = 9.0 Hz, 1H), 4.06 (d, J = 17.4 Hz, 1H), 3.48 (d, J = 17.4 Hz, 1H), 2.01 (d, J = 3.0 Hz, 6H), 1.31-1.29 (m, 1H), 0.77-0.69 (m, 2H), 0.59-0.48 (m, 2H). 139 .sup.1H NMR (300 MHz, Chloroform-d) 8.88 (s, 1H), 8.10 (s, 1H), 7.72 (d, J = 7.2 Hz, 1H), 7.61 (d, J = 9.5 Hz, 1H), 3.95 (d, J = 17.4 Hz, 1H), 3.29 (d, J = 17.4 Hz, 1H), 2.12-2.03 (m, 6H), 1.80 (s, 3H). 140 .sup.1H NMR (300 MHz, Chloroform-d) 8.88 (s, 1H), 8.11 (s, 1H), 7.95 (d, J = 6.6 Hz, 1H), 7.60 (d, J = 8.7 Hz, 1H), 4.15 (d, J = 17.4 Hz, 1H), 3.51 (d, J = 17.4 Hz, 1H), 2.07 (d, J = 3.6 Hz, 6H), 1.83 (s, 3H). 141 .sup.1H NMR (300 MHz, Chloroform-d) 8.84 (s, 1H), 8.06 (s, 1H), 7.80 (d, J = 7.2 Hz, 1H), 7.32 (d, J = 9.0 Hz, 1H), 4.12 (d, J = 17.4 Hz, 1H), 3.46 (d, J = 17.4 Hz, 1H), 2.44-2.38 (m, 1H), 1.82 (s, 3H), 1.70 (s, 3H), 0.99-0.94 (m, 2H), 0.90-0.84 (m, 2H).

[0136] Several methods for preparing the compounds of the present invention are illustrated in detail in the following solutions and examples. Raw materials can be purchased on the market or can be prepared by methods known in literature or as shown in the detailed description. A person skilled in the art should understand that other synthetic routes may also be used to synthesize the compounds of the present invention. Although the specific raw materials and conditions in the synthetic routes have been illustrated below, they may be easily replaced with other similar raw materials and conditions. Various isomers and the like of the compounds resulted from these modifications or variants of the preparation methods of the present invention are all included in the scope of the present invention. In addition, the preparation methods as described below can be further modified according to the disclosure of the present invention using conventional chemical methods well known to a person skilled in the art. For example, the protection for an appropriate group during the reaction, etc.

[0137] The examples of the methods provided below are used to enhance further understanding of the preparation method of the present invention. The specific substances, types and conditions used are determined to further illustrate the present invention and are not intended to limit its reasonable scope. Reagents used in the synthesis of the compounds shown in the following tables are either commercially available or can be easily prepared by a person skilled in the art.

[0138] Examples of representative compounds are as follows. The synthesis methods of other compounds are similar and will not be described in detail here.

1. Synthesis of Compound 10

[0139] (1) Compound 10-1 (52.3 g, 0.21 mmol), ethylene glycol (25.6 g, 0.42 mol), and p-toluenesulfonic acid (3.4 g, 0.02 mol) were dissolved in toluene (500 mL) and reacted at 120 C. for 8 h. When liquid chromatography detected that the raw materials had been completely consumed, the reaction solution was cooled down followed by concentration, added with water, extracted three times with EA, and washed three times with saturated saline solution. The organic phase was dried and concentrated to obtain the crude product which was then stirred and purified through a silica gel column to obtain Compound 10-2 (55.2 g, 0.18 mol) with a yield of 85%.

##STR00214##

[0140] (2) Compound 10-2 (55.2 g, 0.18 mol) was dissolved in 500 mL of ethanol and 100 mL of water, added with iron powder (50 g, 0.9 mol), NH.sub.4Cl (19 g, 0.36 mmol), heated to 60 C. and reacted for 2 h. The liquid chromatography detected the completion of the reaction. The reaction solution was cooled and suction-filtered with a layer of diatomaceous earth on the bottom of the filter flask. The mother liquor was concentrated to obtain the crude product which was then added with ethyl acetate and washed with water to separate liquid phases. The organic phase was concentrated to obtain the crude product which was then stirred and purified through a silica gel column to result in Compound 10-3 (30 g, 0.11 mol), with a yield of 61%.

##STR00215##

[0141] (3) Compound 10-3 (10 g, 38 mmol) was dissolved in 200 mL of acetonitrile, added with bis(pinacolato)diborane 10-4 (48 g, 1.90 mol), and then slowly added dropwise with tert-butyl nitrite (7.8 g, 76 mmol). The system was heated to 60 C. and reacted for 12 h. The LCMS detected disappearance of the raw materials. The reaction solution was concentrated to obtain the crude product which was then extracted with water and ethyl acetate. The organic phase was dried, concentrated, stirred, and purified through a silica gel column to obtain Compound 10-5 (5.5 g, 14.7 mmol) with a yield of 39%.

##STR00216##

[0142] (4) Compound 10-6 (0.4 g, 1.86 mmol), borate 10-5 (1.04 g, 2.80 mmol), and potassium carbonate (0.78 g, 5.6 mmol) were added into a clean flask, added with 20 mL of 1,4-dioxane and 2 mL of water, and then protected by nitrogen and evacuated for 2-3 times. After evacuation, the system was added with 1,1-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (44.74 mg, 54.79 mol), evacuated again, heated to 100 C. and stayed overnight. Upon the completion of the reaction detected by In-Process Control, the solution was treated by decompressing distillation to dry the solvent, washed with water, and extracted for 2-3 times with EA. The EA phase was then washed for 2-3 times with saturated saline solution and added with anhydrous sodium sulfate for drying. The sample was added with silica gel, stirred, and purified by normal phase chromatography to obtain Compound 10-7 (600 mg, 1.42 mmol).

##STR00217##

[0143] (5) Compound 10-7 (0.6 g, 1.42 mmol) and hydroxylamine hydrochloride (0.48 g, 7.1 mmol) were added in a clean flask, added with a mixed solvent of ethanol and water (10 mL:2 mL), and stirred for 3 h at 80 C. Upon the completion of the reaction detected by In-Process Control, the sample was directly stirred and purified by normal phase chromatography to obtain Compound 10-8 (540 mg, 1.36 mmol).

##STR00218##

[0144] (6) Compound 10-8 (0.54 g, 1.36 mmol) and NCS (0.36 g, 2.72 mmol) were added in a clean flask, added with 10 mL of DMF for dissolution, and stirred at 40 C. for 3 h. Upon the completion of the reaction detected by In-Process Control, the sample was washed with water, and then added with EA for extraction (extracted 3 times with a suitable amount of EA). Next, the EA phase was washed twice with saturated saline solution and spin-dried to obtain the white solid 10-9 (580 mg, 1.35 mmol).

##STR00219##

[0145] (7) Compound 10-9 (0.8 g, 0.69 mmol) and triethylamine (0.14 g, 1.38 mmol) were dissolved in DCM, and in ice batch, added dropwise with the dichloromethane solution of Compound 10-10 (0.2 g, 0.46 mmol). After the addition, the ice-water bath was removed and the system stayed at room temperature overnight. Upon the completion of the reaction detected by in-process control, the sample was directly stirred and purified by normal phase chromatography to obtain Compound 10 (70 mg, 0.14 mmol).

##STR00220##

2. Synthesis of Compound 104

[0146] (1) A 100-mL single-necked flask was added in with Compound 104-1 (2 g, 10.62 mmol, 1.0 eq), 16 mL of 1,4-dioxane and 4 mL of water, cesium fluoride (3.23 g, 21.23 mmol, 2.0 eq), Compound 104-2 (2.99 g, 15.92 mmol, 1.5 eq), and a catalytic amount of Pd(dppf)Cl.sub.2 (0.087 g, 0.096 mmol, 0.01 eq). After the addition, the air in the system was replaced with argon gas for 3 times. The reaction solution was stirred overnight at 100 C. The LCMS detected that the reaction of the raw materials was essentially complete with the formation of a major new peak. The reaction solution was rotary-evaporated to remove most of the solvent and 100 mL of water and ethyl acetate (100 mL3) was added for extraction. The organic phase was washed with saturated saline solution (100 mL3), concentrated, then stirred and purified through a silica gel column to obtain Compound 104-3 (2.5 g, 80% yield, pale yellow solid).

##STR00221##

[0147] (2) A 100-mL single-necked flask was sequentially added in with Compound 104-3 (2.5 g, 8.44 mmol, 1.0 eq), AIBN (0.45 g, 2.72 mmol, 0.2 eq), NBS (2.25 g, 12.66 mmol, 1.5 eq), and 30 mL of acetonitrile. Next, the air in the system was replaced with argon gas for 3 times. The reaction solution was stirred overnight at 80 C. The LCMS detected that the reaction of the raw materials was essentially complete with the formation of a major new peak. The reaction solution was rotary-evaporated to remove most of the solvent and 20 mL of water and ethyl acetate (50 mL3) was added for extraction. The organic phase was washed with saturated saline solution (20 mL3) and concentrated to obtain the crude product 104-4 (2.3 g, crude product, yellow solid) which was directly used in the next step.

##STR00222##

[0148] (3) A 100-mL single-necked flask was sequentially added in with Compound 104-4 (2.3 g, 6.13 mmol, 1.0 eq), N-methylmorpholine oxide (1.44 g, 12.23 mmol, 2 eq), and 30 mL of acetonitrile. The reaction solution was stirred overnight at room temperature. The LCMS detected that the reaction of the raw materials was essentially complete with the formation of a major new peak. The reaction solution was rotary-evaporated to remove most of the solvent and 20 mL of water and ethyl acetate (50 mL3) was added for extraction. The organic phase was washed with saturated saline solution (20 mL3) and concentrated to obtain the crude product 104-5 (1.5 g, crude product, yellow solid) which was directly used in the next step.

##STR00223##

[0149] (4) A 100-mL single-necked flask was sequentially added in with Compound 104-5 (1.5 g, 4.84 mmol, 1.0 eq), hydroxylamine hydrochloride (0.34 g, 4.84 mmol, 1 eq), and 25 mL of ethanol. The reaction solution was stirred for three hours at room temperature. The LCMS detected that the reaction of the raw materials was essentially complete with the formation of a major new peak. The reaction solution was rotary-evaporated to remove the solvent and added with 20 mL of water and ethyl acetate (50 mL3) for extraction. The organic phase was washed with saturated saline solution (20 mL3) and concentrated to obtain the crude product 104-6 (1.2 g, crude product, pale yellow solid) which was directly used in the next step.

##STR00224##

[0150] (5) A 100-mL single-necked flask was sequentially added in with Compound 104-6 (1.2 g, 3.69 mmol, 1.0 eq), NCS (0.52 g, 3.87 mmol, 1.05 eq), and 20 mL of DMF. The reaction solution was stirred at room temperature for three hours. The LCMS detected that the reaction of the raw materials was essentially complete with the formation of a major new peak. The system was added with 100 mL of water and ethyl acetate (100 mL3) for extraction. The organic phase was washed with saturated saline solution (20 mL3) and concentrated to obtain the crude product 104-7 (0.9 g, crude product, yellow solid) which was directly used in the next step.

##STR00225##

[0151] (6) At 25 C., a 100-mL single-necked flask was sequentially added in with ethyl methacrylate (0.75 g, 7.51 mmol, 3 eq), triethylamine (0.25 g, 2.5 mmol, 1 eq), and 15 mL of dichloromethane, added dropwise with the dichloromethane solution of Compound 104-7 (0.9 g, 2.5 mmol, 1 eq), and stirred at room temperature for 5 h. The LCMS detected that the reaction of the raw materials was essentially complete with the formation of a major new peak. The system was added with water (100 mL3) for extraction. The organic phase was washed with saturated saline solution (20 mL3) and concentrated to obtain the crude product 104-8 (0.7 g, crude product, yellow oily matter) which was directly used in the next step.

##STR00226##

[0152] (7) At 25 C., a 100-mL single-necked flask was sequentially added in with Compound 104-8 (0.8 g, 1.89 mmol, 1 eq), lithium hydroxide (0.14 g, 5.7 mmol, 3 eq), 15 mL of THF and 5 mL of water and stirred at room temperature for 5 h. The LCMS detected that the reaction of the raw materials was essentially complete with the formation of a major new peak. The pH was adjusted to weak acidity. The system was added with 100 mL of water and ethyl acetate (100 mL3) for extraction. The organic phase was washed with saturated saline solution (20 mL3) and concentrated to obtain the crude product 104-9 (0.7 g, crude product, yellow oily matter) which was directly used in the next step.

##STR00227##

[0153] (8) A 100-mL single-necked flask was added in with Compound 104-9 (0.1 g, 0.24 mmol, 1.0 eq), chloromethyl methyl sulfide (0.047 g, 0.49 mmol, 2 eq), anhydrous potassium carbonate (0.1 g, 0.74 mmol, 3.0 eq), and 10 mL of DMF and reacted at 45 C. for 3 h. The LCMS detected that the reaction of the raw materials was essentially complete with the formation of a major new peak. The system was added with 20 mL of water and ethyl acetate (20 mL3) for extraction. The organic phase was washed with saturated saline solution (20 mL3), concentrated, then stirred and purified through a silica gel column to obtain Compound 104 (0.05 g, 44% yield, colorless oily matter).

##STR00228##

Evaluation of Biological Activity:

[0154] The activity level criteria for plant damage (i.e., growth control rate) are as follows: [0155] Level 10: completely dead; [0156] Level 9: growth control rate greater than or equal to 90% and less than 100%; [0157] Level 8: growth control rate greater than or equal to 80% and less than 90%; [0158] Level 7: growth control rate greater than or equal to 70% and less than 80%; [0159] Level 6: growth control rate greater than or equal to 60% and less than 70%; [0160] Level 5: growth control rate greater than or equal to 50% and less than 60%; [0161] Level 4: growth control rate greater than or equal to 40% and less than 50%; [0162] Level 3: growth control rate greater than or equal to 30% and less than 40%; [0163] Level 2: growth control rate greater than or equal to 20% and less than 30%; [0164] Level 1: growth control rate less than 20%; [0165] Level 0: no effect.

[0166] The above growth control rates are fresh weight control rates.

Post-Emergence Test Experiment:

[0167] Monocotyledonous and dicotyledonous weed seeds (Descurainia sophia, Capsella bursa-pastoris, Abutilon theophrasti, Galium spurium, Stellaria media, Lithospermum arvense, Rorippa indica, Alopecurus aequalis, Alopecurus japonicus, Eleusine indica, Beckmannia syzigachne, Sclerochloa dura, Erigeron canadensis, Phleum paniculatum, Veronica polita, Bromus japonicus, Aegilops tauschii, Phalaris arundinacea, Amaranthus retroflexus, Chenopodium, Commelina communis, Cichorium endivia, Convolvulus arvensis, Cirsium arvense, Solanum nigrum, Acalypha australis, Digitaria sanguinalis, Echinochloa crus-galli, Setaria viridis, Setaria pumila, Leptochloa chinensis, Monochoria vaginalis, Sagittaria trifolia, Schoenoplectiella juncoides, Cyperus rotundus, Cyperus iria, Cyperus difformis, Fimbristylis, Portulaca oleracea, Xanthium sibiricum, Ipomoea nil, Eschenbachia japonica, etc.) and major crop seeds (wheat, maize, paddy rice, soybean, cotton, oilseed rape, millet, sorghum, potato, sesame, castor plant, etc.) were placed in plastic pots filled with soil and then covered with 0.5-2 cm of soil to allow them to grow in a favorable greenhouse environment. Two weeks after sowing, the test plants were treated at the stage of 2-3 leaves. The test compounds of the present invention were individually dissolved with acetone, then added with Tween 80, with 1.5 L/ha of methyl oleate emulsifiable concentrate as a synergist, diluted into solutions of certain concentrations using certain amount of water, and sprayed to the plants using a spray tower. After drug application, the experimental results on weeds were collected after 3 weeks of cultivation in a greenhouse. The compounds were applied at 500, 250, 125, 60, 15, and 7.5 g a.i./ha in triplicate, and the results were averaged. Representative data are listed in Table 3.

TABLE-US-00003 TABLE 3 Results of post-emergence test on weeds Echinochloa Amaranthus Veronica Abutilon Digitaria Setaria Dosage (g No. crus-galli retroflexus polita theophrasti sanguinalis viridis a.i./ha) 1 10 10 10 10 10 10 60 10 10 10 10 10 10 10 60 12 10 10 10 10 10 10 60 15 10 10 10 10 10 10 15 43 10 10 10 10 10 10 15 44 10 10 10 10 10 10 15 45 10 10 10 10 10 10 60 49 10 10 10 10 10 10 15 50 10 10 10 10 10 10 15 51 10 10 10 10 10 10 15 65 10 10 10 10 10 10 15 67 10 10 10 10 10 10 60 68 10 10 10 10 10 10 60 69 10 10 10 10 10 10 60 70 10 10 10 10 10 10 60 71 10 10 10 10 10 10 60 72 10 10 10 10 10 10 60 73 10 10 10 10 10 10 60 74 10 10 10 10 10 10 60 76 10 10 10 10 10 10 15 78 10 10 10 10 10 10 15 97 10 10 10 10 10 10 15 102 10 10 10 10 10 10 60 104 10 10 10 10 10 10 60 105 10 10 10 10 10 10 60 111 10 10 10 10 10 10 60 113 10 10 10 10 10 10 60 127 10 10 10 10 10 10 60 129 10 10 10 10 10 10 60 139 10 10 10 10 10 10 60 140 10 10 10 10 10 10 60 141 10 10 10 10 10 10 60

Pre-Emergence Test Experiment

[0168] Monocotyledonous and dicotyledonous weed seeds as well as major crop seeds (wheat, maize, paddy rice, soybean, cotton, oilseed rape, millet, sorghum) were placed in plastic pots filled with soil and then covered with 0.5-2 cm of soil. The test compounds of the present invention were individually dissolved with acetone, then added with Tween 80, diluted with certain amount of water to obtain solutions of certain concentrations, and sprayed immediately after sowing. After drug application, the experimental results were observed after 4 weeks of cultivation in a greenhouse, showing that most of the drugs of the present invention exhibited outstanding effects at the dose of 250 g a.i./ha., especially on weeds such as Echinochloa crus-galli, Digitaria sanguinalis, Abutilon theophrasti, etc., and many of the compounds had great selectivity to maize, wheat, paddy rice, and soybean.

[0169] Meanwhile, it has been found by experimentations on major weeds in wheat fields and paddy rice fields that the compounds of the present invention generally have good weed control effects; in particular, it has been noticed that the compounds have extremely high activity on broad-leaf weeds and Cyperaceae that are resistant to ALS inhibitors, for example, Sagittaria trifolia, Schoenoplectiella juncoides, Cyperus difformis, Descurainia sophia, Capsella bursa-pastoris, Lithospermum arvense, Galium spurium, Cyperus rotundus, etc., which have excellent commercial values.

[0170] Meanwhile, it has been found by extensive experimentations that many of the compounds of the present invention and compositions thereof have good selectivity to gramineae grasses such as zoysia grass, bermuda grass, tall fescue, bluegrass, ryegrass, seashore paspalum, etc., and can prevent or eliminate many key gramineous weeds and broad-leaf weeds. The experiments on sugarcane, soybean, cotton, oil sunflower, potato, fruit trees, vegetables and the like using different drug application methods also demonstrated excellent selectivity and commercial values.

HETEROCYCLE-SUBSTITUTED AROMATIC COMPOUND, METHOD FOR PREPARING SAME, HERBICIDAL COMPOSITION, AND USE THEREOF

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