PYRIDINE RING-SUBSTITUTED PYRIDAZINOL COMPOUNDS AND DERIVATIVES, PREPARATION METHODS, HERBICIDAL COMPOSITIONS AND APPLICATIONS THEREOF

Abstract

The invention belongs to the technical field of agricultural chemicals, and in particular relates to a pyridine ring-substituted pyridazinol compound and a derivatives thereof, preparation method, herbicidal composition and application thereof. The compound is as shown in Formula I:

##STR00001## wherein, X is halogen, cyano, alkyl, halogenated alkyl, alkoxy, halogenated alkoxy, R.sub.1R.sub.2N(CO), R.sub.1R.sub.2N, hydroxy, or unsubstituted or substituted aryl; Y is independently selected from hydrogen, halogen, cyano, nitro, RO(CH.sub.2).sub.n, and R.sub.1R.sub.2 R.sub.3SiO, etc.; r is an integer from 0 to 4, m is 0 or 1, n and q are independently an integer from 0 to 8, p is an integer from 1 to 8; R is hydrogen, or a halogen-containing or not containing group selected from alkyl, alkenyl, alkynyl, and cycloalkyl, etc.; R.sub.1, R.sub.2, R.sub.3 are each independently hydrogen, nitro, or hydroxy, etc. The compound and the derivative, as well as the composition thereof have very high herbicidal activity and good selectivity, and are safe for crops.

Claims

1. A pyridine ring-substituted pyridazinol compound of Formula I or a derivative thereof: ##STR00502## wherein, X is halogen, cyano, alkyl, halogenated alkyl, alkoxy, halogenated alkoxy, R.sub.1R.sub.2N(CO), R.sub.1R.sub.2N, hydroxy, or unsubstituted or substituted aryl; Y is independently selected from hydrogen, halogen, cyano, nitro, azido, a halogen-containing or not containing group selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, and cycloalkylalkyl, a group selected from aryl, arylalkyl, heteroaryl, and heteroarylalkyl, which is unsubstituted or substituted, RO(CH.sub.2).sub.n, RO(CH.sub.2).sub.pO(CH.sub.2).sub.q, RO(CH.sub.2).sub.pS(CH.sub.2).sub.q, RS(CH.sub.2).sub.n, RS(CH.sub.2).sub.pO(CH.sub.2).sub.q, RS(CH.sub.2).sub.pS(CH.sub.2).sub.q, RO(CH.sub.2).sub.n(CO)(CH.sub.2).sub.q(O).sub.m, RS(CH.sub.2).sub.n(CS)(CH.sub.2).sub.q(S).sub.m, RO(CH.sub.2).sub.n(CO)(CH.sub.2).sub.q(S).sub.m, RO(CH.sub.2).sub.n(CS)(CH.sub.2).sub.q(O).sub.m, RS(CH.sub.2).sub.n(CO)(CH.sub.2).sub.q(O).sub.m, RO(CH.sub.2).sub.n(CS)(CH.sub.2).sub.q(S).sub.m, RS(CH.sub.2).sub.n(CO)(CH.sub.2).sub.q(S).sub.m, RS(CH.sub.2).sub.n(CS)(CH.sub.2).sub.q(O).sub.m, R(CO)(CH.sub.2).sub.n, R(CS)(CH.sub.2).sub.n, R(CO)(CH.sub.2).sub.nO(CH.sub.2).sub.q, R(CS)(CH.sub.2).sub.nS(CH.sub.2).sub.q, R(CO)(CH.sub.2).sub.nS(CH.sub.2).sub.q, R(CS)(CH.sub.2).sub.nO(CH.sub.2).sub.q, RSO(CH.sub.2)(O).sub.m, RSO(CH.sub.2)(S).sub.m, RSO(CH.sub.2).sub.n(NR.sub.3).sub.m, RSO.sub.2(CH.sub.2).sub.n(O).sub.m, RSO.sub.2(CH.sub.2).sub.n(S).sub.m, RSO.sub.2(CH.sub.2).sub.n(NR.sub.3).sub.m, R.sub.1R.sub.2N(CH.sub.2).sub.n, R.sub.1R.sub.2N(CH.sub.2).sub.nO(CH.sub.2).sub.q(O).sub.m, R.sub.1R.sub.2N(CH.sub.2).sub.nO(CH.sub.2).sub.q(S).sub.m, R.sub.1R.sub.2N(CH.sub.2).sub.nO(CH.sub.2).sub.q(NR.sub.3).sub.m, R.sub.1R.sub.2N(CH.sub.2).sub.n(CO)(CH.sub.2).sub.q(O).sub.m, R.sub.1R.sub.2N(CH.sub.2).sub.n(CO)(CH.sub.2).sub.q(S).sub.m, R.sub.1R.sub.2N(CH.sub.2).sub.n(CO)(CH.sub.2).sub.q(NR.sub.3).sub.m, R.sub.1R.sub.2N(CH.sub.2).sub.nSO.sub.2(CH.sub.2).sub.q(O).sub.m, R.sub.1R.sub.2N(CH.sub.2).sub.nSO.sub.2(CH.sub.2).sub.q(S).sub.m, R.sub.1R.sub.2N(CH.sub.2).sub.nSO.sub.2(CH.sub.2).sub.q(NR.sub.3).sub.m, R.sub.1R.sub.2PO.sub.3(O).sub.m(CH.sub.2).sub.q, R.sub.1R.sub.2R.sub.3SiO(CH.sub.2).sub.q, R.sub.1R.sub.2R.sub.3Si(CHCH).sub.m(CH.sub.2).sub.q, R.sub.1R.sub.2CN(O).sub.m(CH.sub.2).sub.n, and R.sub.1R.sub.2CNNH(CH.sub.2); or two adjacent Y form OCH.sub.2O, CH.sub.2CH.sub.2O, OCH.sub.2CH.sub.2O, OCH(CH.sub.3)O, OC(CH.sub.3).sub.2O, OCF.sub.2O, CF.sub.2CF.sub.2O, OCF.sub.2CF.sub.2O, or CHCHCHCH; r is an integer from 0 to 4, m is 0 or 1, n and q are independently an integer from 0 to 8, p is an integer from 1 to 8; R is hydrogen, a halogen-containing or not containing group selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, and cycloalkylalkyl, or a group selected from aryl, arylalkyl, heteroaryl, and heteroarylalkyl, which is unsubstituted or substituted; R.sub.1, R.sub.2, R.sub.3 are each independently hydrogen, nitro, hydroxy, amino, a halogen-containing or not containing group selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkoxyalkyl, alkoxycarbonyl, alkylsulfanylcarbonyl, alkylsulfonyl, alkylsulfonylalkyl, alkylcarbonyl, alkylcarbonylalkyl, alkylcarbonyloxy, alkylamino, alkylaminocarbonyl, alkoxyaminocarbonyl, alkoxycarbonylalkyl, alkylaminocarbonylalkyl, trialkylsilyl, and dialkylphosphonyl, or a group selected from aryl, arylalkyl, aryloxy, arylalkyloxy, aryloxyalkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylalkyloxy, heteroaryloxyalkyl, heteroarylcarbonyl, and heteroarylsulfonyl, which is unsubstituted or substituted; or R.sub.1R.sub.2N forms a 6-membered heterocyclyl, which is unsubstituted or substituted.

2. The pyridine ring-substituted pyridazinol compound or a derivative thereof according to claim 1, wherein, X is halogen, cyano, C.sub.18alkyl, halogenated C.sub.18alkyl, C.sub.18alkoxy, halogenated C.sub.18alkoxy, R.sub.1R.sub.2N(CO), R.sub.1R.sub.2N, hydroxy, or aryl, said aryl is unsubstituted or substituted with 15 substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C.sub.18alkyl, C.sub.38cycloalkyl, C.sub.38cycloalkyl-C.sub.18alkyl, C.sub.28alkenyl, C.sub.28alkynyl, C.sub.18alkoxy, C.sub.18alkylcarbonyl, C.sub.18alkoxycarbonyl, C.sub.18alkylsulfonyl, C.sub.18alkylamino, and C.sub.18alkylcarbonyloxy; Y is independently selected from hydrogen, halogen, cyano, nitro, azido, a halogen-containing or not containing group selected from C.sub.18alkyl, C.sub.28alkenyl, C.sub.28alkynyl, C.sub.38cycloalkyl, C.sub.58cycloalkenyl, and C.sub.38cycloalkyl-C.sub.18alkyl, aryl, aryl-C.sub.18alkyl, heteroaryl, heteroaryl-C.sub.18alkyl, each of said aryl, aryl-C.sub.18alkyl, heteroaryl, or heteroaryl-C.sub.18alkyl is unsubstituted or substituted with 15 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C.sub.18alkyl, C.sub.38cycloalkyl, C.sub.38cycloalkyl-C.sub.18alkyl, C.sub.28alkenyl, C.sub.28alkynyl, C.sub.18alkoxy, C.sub.18alkylcarbonyl, C.sub.18alkoxycarbonyl, C.sub.18alkylsulfonyl, C.sub.18alkylamino, and C.sub.18alkylcarbonyloxy, RO(CH.sub.2).sub.n, RO(CH.sub.2).sub.pO(CH.sub.2).sub.q, RO(CH.sub.2).sub.pS(CH.sub.2).sub.q, RS(CH.sub.2).sub.n, RS(CH.sub.2).sub.pO(CH.sub.2).sub.q, RS(CH.sub.2).sub.pS(CH.sub.2).sub.q, RO(CH.sub.2).sub.n(CO)(CH.sub.2).sub.q, RS(CH.sub.2).sub.n(CS)(CH.sub.2).sub.q, RO(CH.sub.2).sub.n(CS)(CH.sub.2).sub.q, RS(CH.sub.2).sub.n(CO)(CH.sub.2).sub.q, RO(CO)(CH.sub.2).sub.q(O).sub.m, RS(CS)(CH.sub.2).sub.q(S).sub.m, RO(CO)(CH.sub.2).sub.q(S).sub.m, RO(CS)(CH.sub.2).sub.q(O).sub.m, RS(CO)(CH.sub.2).sub.q(O).sub.m, RO(CS)(CH.sub.2).sub.q(S).sub.m, RS(CO)(CH.sub.2).sub.q(S).sub.m, RS(CS)(CH.sub.2).sub.q(O).sub.m, RO(CH.sub.2).sub.n(CO)(O).sub.m, RS(CH.sub.2).sub.n(CS)(S).sub.m, RO(CH.sub.2).sub.n(CO)(S).sub.m, RO(CH.sub.2).sub.n(CS)(O).sub.m, RS(CH.sub.2).sub.n(CO)(O).sub.m, RO(CH.sub.2).sub.n(CS)(S).sub.m, RS(CH.sub.2).sub.n(CO)(S).sub.m, RS(CH.sub.2).sub.n(CS)(O).sub.m, R(CO), R(CS), R(CO)(CH.sub.2).sub.nO, R(CS)(CH.sub.2).sub.nS, R(CO)(CH.sub.2).sub.nS, R(CS)(CH.sub.2).sub.nO, R(CO)O(CH.sub.2).sub.q, R(CS)S(CH.sub.2).sub.q, R(CO)S(CH.sub.2).sub.q, R(CS)(CH.sub.2).sub.q, RSO(O).sub.m, RSO(S).sub.m, RSO(NR.sub.3).sub.m, RSO.sub.2(O).sub.m, RSO.sub.2(S).sub.m, RSO.sub.2(NR.sub.3).sub.m, RSO(CH.sub.2).sub.n, RS.sub.2(CH.sub.2).sub.n, R.sub.1R.sub.2N, R.sub.1R.sub.2N(CH.sub.2).sub.nO(CH.sub.2).sub.q, R.sub.1R.sub.2N(CH.sub.2).sub.n(CO)(CH.sub.2).sub.q, R.sub.1R.sub.2N(CH.sub.2).sub.nSO.sub.2(CH.sub.2).sub.q, R.sub.1R.sub.2N(CH.sub.2).sub.n(CO)(O).sub.m, R.sub.1R.sub.2N(CH.sub.2) (CO)(S).sub.m, R.sub.1R.sub.2N(CH.sub.2).sub.n(CO)(NR.sub.3).sub.m, R.sub.1R.sub.2N(CH.sub.2).sub.nSO.sub.2(O).sub.m, R.sub.1R.sub.2N(CH.sub.2).sub.nSO.sub.2(S).sub.m, R.sub.1R.sub.2N(CH.sub.2).sub.nSO.sub.2(NR.sub.3).sub.m, R.sub.1R.sub.2N(CO)(CH.sub.2)(O).sub.m, R.sub.1R.sub.2N(CO)(CH.sub.2).sub.n(S).sub.m, R.sub.1R.sub.2N(CO)(CH.sub.2)(NR.sub.3).sub.m, R.sub.1R.sub.2NSO.sub.2(CH.sub.2).sub.q(O).sub.m, R.sub.1R.sub.2NSO.sub.2(CH.sub.2).sub.q(S).sub.m, R.sub.1R.sub.2NSO.sub.2(CH.sub.2).sub.q(NR.sub.3).sub.m, R.sub.1R.sub.2N(CH.sub.2).sub.nO, R.sub.1R.sub.2NO(CH.sub.2).sub.q, R.sub.1R.sub.2PO.sub.3(O).sub.m, R.sub.1R.sub.2R.sub.3SiO, R.sub.1R.sub.2R.sub.3Si(CHCH).sub.m, R.sub.1R.sub.2CN(O).sub.m, and R.sub.1R.sub.2CNNH; or two adjacent Y form OCH.sub.2O, CH.sub.2CH.sub.2O, OCH.sub.2CH.sub.2O, OCH(CH.sub.3)O, OC(CH.sub.3).sub.2O, OCF.sub.2O, CF.sub.2CF.sub.2O, OCF.sub.2CF.sub.2O, or CHCHCHCH; r is an integer from 0 to 4, m is 0 or 1, n and q are independently an integer from 0 to 6, p is an integer from 1 to 6; R is hydrogen, a halogen-containing or not containing group selected from C.sub.18alkyl, C.sub.28alkenyl, C.sub.28alkynyl, C.sub.38cycloalkyl, C.sub.58cycloalkenyl, and C.sub.38cycloalkyl-C.sub.18alkyl, aryl, aryl-C.sub.18alkyl, heteroaryl, or heteroaryl-C.sub.18alkyl, each of said aryl, aryl-C.sub.18alkyl, heteroaryl, or heteroaryl-C.sub.18alkyl is unsubstituted or substituted with 15 groups substituents independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C.sub.18alkyl, C.sub.38cycloalkyl, C.sub.38cycloalkyl-C.sub.18alkyl, C.sub.28alkenyl, C.sub.28alkynyl, C.sub.18alkoxy, C.sub.18alkylcarbonyl, C.sub.18alkoxycarbonyl, C.sub.18alkylsulfonyl, C.sub.18alkylamino, and C.sub.18alkylcarbonyloxy; R.sub.1, R.sub.2, R.sub.3 are each independently hydrogen, nitro, hydroxy, amino, a halogen-containing or not containing group selected from C.sub.18alkyl, C.sub.28alkenyl, C.sub.28alkynyl, C.sub.38cycloalkyl, C.sub.58cycloalkenyl, C.sub.38cycloalkyl-C.sub.18alkyl, C.sub.18alkoxy, C.sub.28alkenyloxy, C.sub.28alkynyloxy, C.sub.38cycloalkyloxy, C.sub.18alkoxy-C.sub.18alkyl, C.sub.18alkoxycarbonyl, C.sub.18alkylcarbonyl-C.sub.18alkyl, C.sub.18alkylsulfanylcarbonyl, C.sub.18alkylsulfonyl, C.sub.18alkylsulfonyl-C.sub.18alkyl, C.sub.18alkylcarbonyl, C.sub.18alkylcarbonyloxy, C.sub.18alkylamino, C.sub.18alkylaminocarbonyl, C.sub.18alkoxyaminocarbonyl, C.sub.18alkoxycarbonyl-C.sub.18alkyl, C.sub.18alkylaminocarbonyl-C.sub.18alkyl, triC.sub.18alkylsilyl, and diC.sub.18alkylphosphonyl, aryl, aryl-C.sub.18alkyl, aryloxy, aryl-C.sub.18alkyloxy, aryloxy-C.sub.18alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C.sub.18alkyl, heteroaryloxy, heteroaryl-C.sub.18alkyloxy, heteroaryloxy-C.sub.18alkyl, heteroarylcarbonyl, or heteroarylsulfonyl, each of said aryl, aryl-C.sub.18alkyl, aryloxy, aryl-C.sub.18alkyloxy, aryloxy-C.sub.18alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C.sub.18alkyl, heteroaryloxy, heteroaryl-C.sub.18alkyloxy, heteroaryloxy-C.sub.18alkyl, heteroarylcarbonyl, or heteroarylsulfonyl is unsubstituted or substituted with 15 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C.sub.18alkyl, C.sub.38cycloalkyl, C.sub.38cycloalkyl-C.sub.18alkyl, C.sub.28alkenyl, C.sub.28alkynyl, C.sub.18alkoxy, C.sub.18alkylcarbonyl, C.sub.18alkoxycarbonyl, C.sub.18alkylsulfonyl, C.sub.18alkylamino, and C.sub.18alkylcarbonyloxy; or R.sub.1R.sub.2N-forms a 6-membered heterocyclyl containing or not containing other hetero atoms, which is unsubstituted or substituted by at least one group selected from the group consisting of C.sub.18alkyl, halogenated C.sub.18alkyl, C.sub.18alkoxy, halogenated C.sub.18alkoxy, C.sub.18alkoxycarbonyl, and halogen; the derivative refers to an agriculturally acceptable derivative of the 4-hydroxy of the pyridazine ring of Formula I.

3. The pyridine ring-substituted pyridazinol compound or a derivative thereof according to claim 1 or 2, wherein, X is fluorine, chlorine, bromine, cyano, C.sub.16alkyl, halogenated C.sub.16alkyl, C.sub.16alkoxy, halogenated C.sub.16alkoxy, R.sub.1R.sub.2N(CO), R.sub.1R.sub.2N, hydroxy, or phenyl, said phenyl is unsubstituted or substituted with 1-3 substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C.sub.16alkyl, C.sub.36cycloalkyl, C.sub.36cycloalkyl-C.sub.16alkyl, C.sub.26alkenyl, C.sub.26alkynyl, C.sub.16alkoxy, C.sub.16alkylcarbonyl, C.sub.16alkoxycarbonyl, C.sub.16alkylsulfonyl, C.sub.16alkylamino, and C.sub.16alkylcarbonyloxy; Y is independently selected from hydrogen, fluorine, chlorine, bromine, cyano, nitro, azido, a fluoro-, chloro-, or bromo-containing or not containing group selected from C.sub.16alkyl, C.sub.26alkenyl, C.sub.26alkynyl, C.sub.36cycloalkyl, C.sub.56cycloalkenyl, and C.sub.36cycloalkyl-C.sub.16alkyl, aryl, aryl-C.sub.16alkyl, heteroaryl, heteroaryl-C.sub.16alkyl, each of said aryl, aryl-C.sub.16alkyl, heteroaryl, or heteroaryl-C.sub.16alkyl is unsubstituted or substituted with 13 groups independently selected from fluorine, chlorine, bromine, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a fluoro-, chloro-, or bromo-containing or not containing group selected from C.sub.16alkyl, C.sub.36cycloalkyl, C.sub.36cycloalkyl-C.sub.16alkyl, C.sub.26alkenyl, C.sub.26alkynyl, C.sub.16alkoxy, C.sub.16alkylcarbonyl, C.sub.16alkoxycarbonyl, C.sub.16alkylsulfonyl, C.sub.16alkylamino, and C.sub.16alkylcarbonyloxy, RO, RO(CH.sub.2).sub.pO, RO(CH.sub.2).sub.pS, RS, RS(CH.sub.2).sub.pO, RS(CH.sub.2).sub.pS, RO(CO)(O).sub.m, RS(CS)(S).sub.m, RO(CO)(S).sub.m, RO(CS)(O).sub.m, RS(CO)(O).sub.m, RO(CS)(S).sub.m, RS(CO)(S).sub.m, RS(CS)(O).sub.m, RO(CO)(CH.sub.2).sub.q, RS(CS)(CH.sub.2).sub.q, RO(CS)(CH.sub.2).sub.q, RS(CO)(CH.sub.2).sub.q, RO(CH.sub.2)(CO), RS(CH.sub.2).sub.n(CS), RO(CH.sub.2).sub.n(CS), RSO, RSO.sub.2, R.sub.1R.sub.2N, R.sub.1R.sub.2NO, R.sub.1R.sub.2N(CO)(CH.sub.2).sub.p, R.sub.1R.sub.2N(CO)(O).sub.m, R.sub.1R.sub.2N(CO)(S).sub.m, R.sub.1R.sub.2N(CO)(NR.sub.3).sub.m, R.sub.1R.sub.2NSO.sub.2(CH.sub.2).sub.p, R.sub.1R.sub.2NSO.sub.2, R.sub.1R.sub.2N(CH.sub.2).sub.p(CO), R.sub.1R.sub.2N(CH.sub.2).sub.pSO.sub.2, R.sub.1R.sub.2N(CH.sub.2).sub.pO, R.sub.1R.sub.2NO(CH.sub.2).sub.p, R.sub.1R.sub.2PO.sub.3, R.sub.1R.sub.2R.sub.3SiO, R.sub.1R.sub.2R.sub.3Si, R.sub.1R.sub.2R.sub.3SiCHCH, R.sub.1R.sub.2CN, R.sub.1R.sub.2CNO, and R.sub.1R.sub.2CNNH; or two adjacent Y form CHCHCHCH; r is 0, 1, 2, 3 or 4, m is 0 or 1, n and q are independently 0, 1, 2, 3 or 4, p is 1, 2, 3 or 4; R is hydrogen, a fluoro-, chloro-, or bromo-containing or not containing group selected from C.sub.16alkyl, C.sub.26alkenyl, C.sub.26alkynyl, C.sub.36cycloalkyl, C.sub.56cycloalkenyl, and C.sub.36cycloalkyl-C.sub.16alkyl, aryl, aryl-C.sub.16alkyl, heteroaryl, or heteroaryl-C.sub.16alkyl, each of said aryl, aryl-C.sub.16alkyl, heteroaryl, or heteroaryl-C.sub.16alkyl is unsubstituted or substituted with 1-3 substituents independently selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a fluoro-, chloro-, or bromo-containing or not containing group selected from C.sub.16alkyl, C.sub.36cycloalkyl, C.sub.36cycloalkyl-C.sub.16alkyl, C.sub.26alkenyl, C.sub.26alkynyl, C.sub.16alkoxy, C.sub.16alkylcarbonyl, C.sub.16alkoxycarbonyl, C.sub.16alkylsulfonyl, C.sub.16alkylamino, and C.sub.16alkylcarbonyloxy; R.sub.1, R.sub.2, R.sub.3 are each independently hydrogen, nitro, hydroxy, amino, a fluoro-, chloro-, or bromo-containing or not containing group selected from C.sub.16alkyl, C.sub.26alkenyl, C.sub.26alkynyl, C.sub.36cycloalkyl, C.sub.56cycloalkenyl, C.sub.36cycloalkyl-C.sub.16alkyl, C.sub.16alkoxy, C.sub.26 alkenyloxy, C.sub.26 alkynyloxy, C.sub.36 cycloalkyloxy, C.sub.16 alkoxy-C.sub.16 alkyl, C.sub.16 alkoxycarbonyl, C.sub.16 alkylsulfanylcarbonyl, C.sub.16 alkylsulfonyl, C.sub.16 alkylsulfonyl-C.sub.16 alkyl, C.sub.16 alkylcarbonyl, C.sub.16 alkylcarbonyl-C.sub.16 alkyl, C.sub.16 alkylcarbonyloxy, C.sub.16 alkylamino, C.sub.16 alkylaminocarbonyl, C.sub.16 alkoxyaminocarbonyl, C.sub.16 alkoxycarbonyl-C.sub.16 alkyl, C.sub.16 alkylaminocarbonyl-C.sub.16 alkyl, triC.sub.16 alkylsilyl, and diC.sub.16 alkylphosphonyl, aryl, aryl-C.sub.16 alkyl, aryloxy, aryl-C.sub.16 alkyloxy, aryloxy-C.sub.16 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C.sub.16 alkyl, heteroaryloxy, heteroaryl-C.sub.16 alkyloxy, heteroaryloxy-C.sub.16 alkyl, heteroarylcarbonyl, or heteroarylsulfonyl, each of said aryl, aryl-C.sub.16 alkyl, aryloxy, aryl-C.sub.16 alkyloxy, aryloxy-C.sub.16 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C.sub.16 alkyl, heteroaryloxy, heteroaryl-C.sub.16 alkyloxy, heteroaryloxy-C.sub.16 alkyl, heteroarylcarbonyl, or heteroarylsulfonyl is unsubstituted or substituted with 13 groups independently selected from fluorine, chlorine, bromine, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a fluoro-, chloro-, or bromo-containing or not containing group selected from C.sub.16 alkyl, C.sub.36 cycloalkyl, C.sub.36 cycloalkyl-C.sub.16 alkyl, C.sub.26 alkenyl, C.sub.26 alkynyl, C.sub.16 alkoxy, C.sub.16 alkylcarbonyl, C.sub.16 alkoxycarbonyl, C.sub.16 alkylsulfonyl, C.sub.16 alkylamino, and C.sub.16 alkylcarbonyloxy; or R.sub.1R.sub.2N is selected from ##STR00503## the aryl is selected from ##STR00504## the heteroaryl is selected from ##STR00505## ##STR00506## ##STR00507## R is hydrogen, nitro, hydroxy, amino, a fluoro-, chloro-, or bromo-containing or not containing group selected from C.sub.16 alkyl, C.sub.26 alkenyl, C.sub.26 alkynyl, C.sub.36 cycloalkyl, C.sub.56 cycloalkenyl, C.sub.36 cycloalkyl-C.sub.16 alkyl, C.sub.16 alkoxy, C.sub.26 alkenyloxy, C.sub.26 alkynyloxy, C.sub.36 cycloalkyloxy, C.sub.16 alkoxy-C.sub.16 alkyl, C.sub.16 alkoxycarbonyl, C.sub.16 alkylsulfanylcarbonyl, C.sub.16 alkylsulfonyl, C.sub.16 alkylsulfonyl-C.sub.16alkyl, C.sub.16 alkylcarbonyl, C.sub.16 alkylcarbonyl-C.sub.16 alkyl, C.sub.16 alkylcarbonyloxy, C.sub.16 alkylamino, C.sub.16 alkylaminocarbonyl, C.sub.16 alkoxyaminocarbonyl, C.sub.16 alkoxycarbonyl-C.sub.16 alkyl, C.sub.16 alkylaminocarbonyl-C.sub.16 alkyl, triC.sub.16 alkylsilyl, and diC.sub.16 alkylphosphonyl, ##STR00508## aryl, aryl-C.sub.16 alkyl, aryloxy, aryl-C.sub.16 alkyloxy, aryloxy-C.sub.16 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C.sub.16 alkyl, heteroaryloxy, heteroaryl-C.sub.16 alkyloxy, heteroaryloxy-C.sub.16 alkyl, heteroarylcarbonyl, or heteroarylsulfonyl, each of said ##STR00509## aryl, aryl-C.sub.16 alkyl, aryloxy, aryl-C.sub.16 alkyloxy, aryloxy-C.sub.16 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C.sub.16 alkyl, heteroaryloxy, heteroaryl-C.sub.16 alkyloxy, heteroaryloxy-C.sub.16 alkyl, heteroarylcarbonyl, or heteroarylsulfonyl is unsubstituted or substituted with 13 groups independently selected from fluorine, chlorine, bromine, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a fluoro-, chloro-, or bromo-containing or not containing group selected from C.sub.16 alkyl, C.sub.36 cycloalkyl, C.sub.36 cycloalkyl-C.sub.16 alkyl, C.sub.26 alkenyl, C.sub.2-6 alkynyl, C.sub.16 alkoxy, C.sub.16 alkylcarbonyl, C.sub.16 alkoxycarbonyl, C.sub.16 alkylsulfonyl, C.sub.16 alkylamino, and C.sub.16 alkylcarbonyloxy; the derivative refers to an agriculturally acceptable derivative of the 4-hydroxy of the pyridazine ring of Formula I, including a salt, an ester, a hydrazine, a hydroxylamine, an ether thereof, and the like.

4. The pyridine ring-substituted pyridazinol compound or a derivative thereof according to claim 1 or 2, wherein, X represents chlorine, cyano, methyl, ethyl, trifluoromethyl, pentafluoroethyl, difluoromethyl, monofluoromethyl, methoxy, ethoxy, trifluoromethoxy, pentafluoroethoxy or ##STR00510## r is 0, 1, 2, 3, or 4; each Y independently represents hydrogen, methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, bromine, amino, cyano, trifluoromethyl, ##STR00511## or ##STR00512## the derivative refers to an agriculturally acceptable derivative of the 4-hydroxy of the pyridazine ring of Formula I, including a salt, an ester, a hydrazine, a hydroxylamine, an ether thereof, and the like.

5. A method for preparing a pyridine ring-substituted pyridazinol compound or derivative thereof according to any one of claims 1 to 4, comprising: the method for preparing the pyridine ring-substituted pyridazinol compound, comprising the steps of: (1) subjecting a compound of Formula II and a compound of Formula III to Suzuki reaction to obtain a compound of Formula IV; (2) subjecting a compound of Formula IV to halogenating reaction to obtain a compound of Formula V; (3) subjecting a compound of Formula V to hydrolysis reaction to obtain a compound of Formula I; wherein the reaction route is as follows: ##STR00513## L.sub.1, L.sub.2 each independently represent halogen, preferably chlorine, bromine, or iodine. the reaction route for preparing an ester or ether derivative is as follows: ##STR00514## wherein, Q.sub.1 is a halogen, preferably chlorine or bromine; the reaction route for preparing an oxime or hydroxylamine derivative is as follows: ##STR00515## wherein, Q.sub.2 is a halogen, preferably chlorine or fluorine.

6. The method for preparing a pyridine ring-substituted pyridazinol compound or derivative thereof according to claim 5, wherein, The reactions are carried out in the range of 20 to 150 C., preferably 50 to 130 C.; steps (1) is carried out in the presence of a catalyst, a base and a solvent, wherein the catalyst is Pd(dppf)Cl.sub.2CH.sub.2Cl.sub.2, Pd(dba).sub.2, Pd.sub.2(dba).sub.3, Pd(PPh.sub.3).sub.4, PdCl.sub.2, Pd(OAc).sub.2, Pd(dppf)Cl.sub.2, Pd(PPh.sub.3).sub.2C.sub.2, or Ni(dppf)Cl.sub.2, the base is one or more selected from Et.sub.3N, NaHCO.sub.3, KOAc, K.sub.2CO.sub.3, K.sub.3PO.sub.4, Na.sub.2CO.sub.3, CsF, Cs.sub.2CO.sub.3, t-BuONa, EtONa, KOH, and NaOH, the solvent is THF/water, toluene/water, DMF/water, 1,4-dioxane/water, toluene/ethanol/water, acetonitrile/water, THF, toluene, 1,4-dioxane, acetonitrile, or DMF system; step (2) is carried out in the presence of a halogenated reagent, a catalyst and a solvent, wherein the halogenated reagent is N-chloro succinimide, N-bromo succinimide or N-iodo succinimide, the catalyst is benzoyl peroxide, and the solvent is acetonitrile; steps (3) is carried out in the presence of a base and a solvent or in the presence of a solution of boron tribromide, a solution of hydrobromic acid in acetic acid, a solution of hydrochloric acid in methanol or a solution of hydrochloric acid in ethyl acetate, the base is preferably selected from NaOH, KOH, potassium acetate, and sodium acetate, the solvent is preferably water or DMSO; reactions for preparing the ester or ether derivatives and the second step for preparing the oxime or hydroxylamine derivatives are carried out in the presence of a base and a solvent, the base is one or more selected from the group consisting of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, cesium carbonate, triethylamine and diisopropylethylamine; the solvent is THF, 1,4-dioxane, toluene, 1,2-dichloroethane, ethyl acetate, acetonitrile, DMF, acetone, dichloromethane, or chloroform; the first step for preparing the oxime and hydroxylamine derivative is carried out in the presence of a halogenation reagent and a solvent, wherein the halogenation reagent is Phenofluor/cesium fluoride or POCl.sub.3, and the solvent is one or more selected from the group consisting of toluene, 1,2-dichloroethane, and DMF; the reaction temperature is in the range of 0 to 120 C., preferably 20 to 80 C.

7. A herbicidal composition, comprising component (i) a pyridine ring-substituted pyridazinol compound of Formula I or a derivative thereof according to any one of claims 1 to 4; preferably, further comprising component (ii) one or more additional herbicides and/or safeners; more preferably, further comprising component (iii) an agriculturally acceptable formulation auxiliary.

8. The herbicidal composition according to claim 7, wherein the additional herbicide is selected from the group consisting of an HPPD inhibitor, a hormone herbicide, and a PDS inhibitor; preferably, the HPPD inhibitor is selected from the group consisting of Sulcotrione, Mesotrione, Topramezone, Tembotrione, Bicyclopyrone, Tefuryltrione, Benzobicyclon, Lancotrione, Shuangzuocaotong, Huanbifucaotong, Sanzuohuangcaotong, Benzuofucaotong, Pyrasulfotole, Pyrazolate, Benzofenap, Tolpyralate, Fenquinotrione, and Isoxaflutole; the hormone herbicide is selected from the group consisting of Fluroxypyr, Halauxifen-methyl, Florpyrauxifen-benzyl, Quinclorac, Quinmerac, 2-methyl-4-chlorophenoxy acetic acid, 2-methyl-4-chlorophenoxypropionic acid, MCPB, 2,4-D, Dichlorprop, 2,4-DB, Dicamba, Picloram, Trichlopyr, Clopyralid, Triclopyr and derivatives thereof, the PDS inhibitor is selected from the group consisting of Flurochloridone, Flurtamone, Diflufenican, Picolinafen, Beflubutamid, Norflurazon and Fluridone.

9. A method for controlling a harmful plant, comprising applying at least one of herbicidally effective amount of the pyridine ring-substituted pyridazinol compound or derivative thereof according to any one of claims 1 to 4, or the herbicidal composition according to any one of claims 7 to 8 to the harmful plant or an area with the harmful plant.

10. Use of at least one of the pyridine ring-substituted pyridazinol compound or derivative thereof according to any one of claims 1 to 4, or the herbicidal composition according to any one of claims 7 to 8 for controlling a harmful plant; preferably, the pyridine ring-substituted pyridazinol compound or derivative thereof is used to control a harmful plant in a useful crop, the useful crop is a genetically modified crop or a crop treated by genome editing technique.

Description

SPECIFIC MODE FOR CARRYING OUT THE INVENTION

[0093] 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.

[0094] 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 1-5. The structure and information of a certain compound are shown in Table 1-5. The compounds in Table 1-5 are listed for further explication of the present invention, other than any limit therefor. The subject of the present invention should not be interpreted by those skilled in the art as being limited to the following compounds.

TABLE-US-00001 TABLE 1 Structure and .sup.1HNMR data of Compound(1) (1) [00034] No. X Y .sup.1HNMR 1-1 Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.16 (s, 1H), 8.90 (d, J = 1.2 Hz, 1H), 8.41 (dd, J = 5.0, 1.2 Hz, 1H), 8.13-8.08 (m, 1H), 7.48-7.37 (m, 1H), 7.39 (s, 1H). 1-2 Cl 2-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.97 (s, 1H), 8.21-8.05 (m, 2H), 7.76-7.73 (m, 1H), 7.52 (s, 1H). 1-3 Cl 4-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.01 (s, 1H), 8.71-8.66 (m, 1H), 8.11-7.85 (m, 1H), 7.43 (s, 1H), 7.14-7.06 (m, 1H). 1-4 Cl 5-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.05 (s, 1H), 8.63 (d, J = 1.5 Hz, 1H), 8.45 (dd, J = 8.0, 1.5 Hz, 1H), 8.23-8.16 (m, 1H), 7.43 (s, 1H). 1-5 Cl 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.05 (s, 1H), 8.94 (d, J = 5.0 Hz, 1H), 8.53-8.48 (m, 1H), 7.49 (s, 1H), 7.32 (dd, J = 11.0, 5.5 Hz, 1H). 1-6 Cl 2-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.95 (s, 1H), 8.11-8.02 (m, 2H), 7.76-7.70 (m, 1H), 7.50 (s, 1H). 1-7 Cl 4-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.02 (s, 1H), 8.88 (d, J = 1.5 Hz, 1H), 7.90 (dd, J = 8.0, 1.5 Hz, 1H), 7.51 (d, J = 8.0 Hz, 1H), 7.43 (s, 1H). 1-8 Cl 5-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.01 (s, 1H), 8.85 (d, J = 1.0 Hz, 1H), 8.71 (d, J = 1.0 Hz, 1H), 8.09-8.02 (m, 1H), 7.44 (s, 1H). 1-9 Cl 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.21 (s, 1H), 8.85 (s, 1H), 8.49 (d, J = 5.0 Hz, 1H), 7.61 (d, J = 5.0 Hz, 1H), 7.42 (s, 1H). 1-10 Cl 2-, Br .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.13 (s, 1H), 8.30 (dd, J = 4.5, 1.5 Hz, 1H), 7.87- 7.78 (m, 2H), 7.43 (s, 1H). 1-11 Cl 4-, Br .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.00 (s, 1H), 8.73 (d, J = 1.5 Hz, 1H), 7.81 (dd, J = 8.0, 1.5 Hz, 1H), 7.71 (d, J = 8.0 Hz, 1H), 7.43 (s, 1H). 1-12 Cl 5-, Br .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.98 (s, 1H), 8.94 (d, J = 1.0 Hz, 1H), 8.69 (d, J = 1.5 Hz, 1H), 8.25-8.20 (m, 1H), 7.44 (s, 1H). 1-13 Cl 6-, Br .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.09 (s, 1H), 8.87 (s, 1H), 8.51 (d, J = 5.0 Hz, 1H), 7.83 (d, J = 5.0 Hz, 1H), 7.43 (s, 1H). 1-14 Cl 2-, I .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.07 (s, 1H), 8.24 (dd, J = 5.0, 1.0 Hz, 1H), 7.72 (dd, J = 8.0, 5.0 Hz, 1H), 7.57 (dd, J = 8.0, 1.0 Hz, 1H), 7.44 (s, 1H). 1-15 Cl 4-, I .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.98 (s, 1H), 8.53 (d, J = 1.0 Hz, 1H), 7.76 (d, J = 8.0 Hz, 1H), 7.52 (dd, J = 8.0, 1.0 Hz, 1H), 7.43 (s, 1H). 1-16 Cl 5-, I .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.96 (s, 1H), 8.84-8.78 (m, 2H), 8.33 (d, J = 1.5 Hz, 1H), 7.44 (s, 1H). 1-17 Cl 6-, I .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.03 (s, 1H), 8.66 (s, 1H), 8.27 (d, J = 5.0 Hz, 1H), 7.96 (d, J = 5.0 Hz, 1H), 7.44 (s, 1H). 1-18 Cl 2-, Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.08 (s, 1H), 8.66 (dd, J = 5.0, 1.0 Hz, 1H), 7.76- 7.58 (m, 2H), 7.42 (s, 1H), 2.80 (s, 3H). 1-19 Cl 4-, Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.95 (s, 1H), 9.10 (d, J = 1.0 Hz, 1H), 8.10 (dd, J = 8.0, 1.0 Hz, 1H), 7.45-7.33 (m, 2H), 2.57 (s, 3H). 1-20 Cl 5-, Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.96 (s, 1H), 8.75-8.44 (m, 2H), 7.79-7.68 m, 1H), 7.45 (s, 1H), 2.28 (s, 3H). 1-21 Cl 6-, Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.11 (s, 1H), 8.78 (s, 1H), 8.55 (d, J = 5.0 Hz, 1H), 7.43 (d, J = 5.0 Hz, 2H), 2.44 (s, 3H). 1-22 Cl 2-, CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.10 (s, 1H), 8.72-8.64 (m, 1H), 7.86-7.79 (m, 2H), 7.41 (s, 1H). 1-23 Cl 4-, CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.06 (s, 1H), 9.17 (d, J = 1.5 Hz, 1H), 8.25 (dd, J = 8.0, 1.5 Hz, 1H), 7.75 (d, J = 8.0 Hz, 1H), 7.42 (s, 1H). 1-24 Cl 5-, CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.18 (s, 1H), 9.01 (d, J = 1.5 Hz, 1H), 8.71 (s, 1H), 8.21 (s, 1H), 7.40 (s, 1H). 1-25 Cl 6-, CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.13 (s, 1H), 8.92 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.75-7.70 (m, 1H), 7.39 (s, 1H). 1-26 Cl 2-, CN .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.07 (s, 1H), 8.69-8.56 (m, 1H), 8.15-8.04 (m, 2H), 7.43 (s, 1H). 1-27 Cl 6-, CN .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.10 (s, 1H), 9.15 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 8.02 (d, J = 5.0 Hz, 1H), 7.42 (s, 1H). 1-28 Cl 2-, OMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.08 (s, 1H), 8.16-8.08 (m, 1H), 7.71-7.09 (m, 2H), 7.42 (s, 1H), 4.06 (s, 3H). 1-29 Cl 4-, OMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.17 (s, 1H), 8.67 (d, J = 1.0 Hz, 1H), 7.88 (dd, J = 8.0, 1.0 Hz, 1H), 7.39 (s, 1H), 6.98 (d, J = 8.0 Hz, 1H), 3.90 (s, 3H). 1-30 Cl 5-, OMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.17 (s, 1H), 8.61 (d, J = 1.5 Hz, 1H), 8.23 (d, J = 1.0 Hz, 1H), 7.60-7.55 (m, 1H), 7.39 (s, 1H), 3.74 (s, 3H). 1-31 Cl 4-, NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.16 (s, 1H), 8.26-8.00 (m, 1H), 7.38 (s, 1H), 6.82 (d, J = 8.0 Hz, 1H), 6.62 (d, J = 8.0 Hz, 1H), 5.30 (br, 2H). 1-32 Cl 5-, NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.17 (s, 1H), 8.40 (d, J = 1.5 Hz, 1H), 8.05 (d, J = 1.5 Hz, 1H), 7.39-7.30 (m, 2H), 6.18 (s, 2H). 1-33 Cl 4-,[00035] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.20 (s, 1H), 9.17 (d, J = 1.0 Hz, 1H), 8.18 (d, J = 8.0, 1.0 Hz, 1H), 7.83 (d, J = 8.0 Hz, 1H), 7.40 (s, 1H). 1-34 Cl 5-,[00036] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.19 (s, 1H), 9.26 (d, J = 1.5 Hz, 1H), 9.11 (d, J = 1.5 Hz, 1H), 8.51-8.43 (m, 1H), 7.40 (s, 1H). 1-35 Cl 5-,[00037] 1-36 Cl 4-,[00038] 1-37 Cl 4-,[00039] 1-38 Cl 6-,[00040] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.22 (s, 1H), 8.92 (s, 1H), 8.51 (d, J = 5.0 Hz, 1H), 7.47 (s, 1H), 7.25 (d, J = 5.0 Hz, 1H), 3.91 (s, 3H). 1-39 Cl 2-,[00041] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.19 (s, 1H), 8.15-8.01 (m, 1H), 7.76-7.49 (m, 3H), 4.39 (q, J = 8.0 Hz, 2H), 1.36 (t, J = 8.0 Hz, 3H). 1-40 Cl 4-,[00042] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.17 (s, 1H), 9.07 (d, J = 1.0 Hz, 1H), 8.10-7.79 (m, 2H), 6.57 (d, J = 8.0 Hz, 1H), 3.88- 3.75 (m, 4H), 3.55-3.41 (m, 4H). 1-41 Cl 4-,[00043] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.18 (s, 1H), 9.09 (d, J = 1.3 Hz, 1H), 8.12-7.70 (m, 2H), 6.57 (d, J = 8.0 Hz, 1H), 3.66- 3.41 (m, 8H), 1.21 (s, 9H). 1-42 Cl 4-,[00044] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.97 (s, 1H), 8.59 (d, J = 1.5 Hz, 1H), 7.79-7.45 (m, 2H), 7.04 (d, J = 8.0 Hz, 1H), 4.53 (s, 2H), 4.05 (t, J = 7.5 Hz, 2H), 3.33 (s, 3H), 2.40-2.10 (m, 4H). 1-43 Cl 5-,[00045] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.82 (s, 1H), 8.68-8.61 (m, 2H), 8.02-7.99 (m, 1H), 7.47 (s, 1H), 4.25 (s, 2H), 3.67 (s, 3H). 1-44 Cl 4-,[00046] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.00 (s, 1H), 8.97 (d, J = 1.5 Hz, 1H), 7.97-7.45 (m, 2H), 6.92 (d, J = 8.0 Hz, 1H), 3.36 (s, 3H), 3.03 (s, 3H). 1-45 Cl 5-,[00047] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.20 (s, 1H), 8.61-8.28 (m, 2H), 7.59-7.40 (m, 2H), 5.22 (s, 2H), 2.61 (q, J = 8.0 Hz, 2H), 1.31 (t, J = 8.0 Hz, 3H). 1-46 Cl 4-,[00048] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.17 (s, 1H), 8.69 (d, J = 1.0 Hz, 1H), 7.89 (dd, J = 8.0, 1.0 Hz, 1H), 7.39 (s, 1H), 7.06 (d, J = 8.0 Hz, 1H), 4.72 (s, 2H), 2.88 (s, 6H). 1-47 Cl 4-,[00049] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.18 (s, 1H), 8.32-8.10 (m, 2H), 7.42-7.33 (m, 3H), 7.24-7.18 (m, 2H), 7.09-7.68 (m, 1H), 6.92 (d, J = 8.0 Hz, 1H), 3.31 (s, 3H). 1-48 Cl 4-,[00050] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.16 (s, 1H), 8.67 (d, J = 1.0 Hz, 1H), 7.88-7.69 (m, 2H), 7.05 (d, J = 8.0 Hz, 1H), 4.05 (t, J = 7.2 Hz, 2H), 3.08 (t, J = 7.2 Hz, 2H), 2.45 (s, 6H). 1-49 Cl 5-,[00051] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.17 (s, 1H), 8.91-8.72 (m, 2H), 8.18-8.10 (m, 1H), 7.39 (s, 1H), 4.67 (s, 2H), 4.35 (s, 2H), 2.31-2.18 (m, 1H), 1.88 (s, 1H), 0.66- 0.55 (m, 2H), 0.55-0.47 (m, 2H). 1-50 Cl 4-,[00052] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.17 (s, 1H), 9.01 (d, J = 1.0 Hz, 1H), 8.02-7.93 (m, 2H), 7.39 (s, 1H), 3.78 (s, 6H). 1-51 Cl 5-,[00053] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.18 (s, 1H), 8.83-8.44 (m, 2H), 7.77-7.65 (m, 1H), 7.39 (s, 1H), 0.21 (s, 9H). 1-52 CF.sub.3 4-,[00054] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.94 (s, 1H), 8.88 (d, J = 1.5 Hz, 1H), 7.74-7.56 (m, 2H), 7.47-7.01 (m, 2H), 6.31 (d, J = 11.0 Hz, 1H), 0.08 (s, 9H). 1-53 Cl 4-,[00055] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.05 (s, 1H), 8.85 (d, J = 1.2 Hz, 1H), 7.85-7.79 (m, 2H), 7.42 (s, 1H), 0.33 (s, 9H). 1-54 Cl 4-,[00056] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.16 (s, 1H), 8.89 (d, J = 1.0 Hz, 1H), 7.86 (dd, J = 8.0, 1.0 Hz, 1H), 7.43-7.37 (m, 2H), 1.92 (s, 6H). 1-55 Cl 4-,[00057] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.22 (s, 1H), 8.76 (d, J = 1.5 Hz, 1H), 7.89-7.68 (m, 2H), 7.06 (d, J = 8.0 Hz, 1H), 2.48 (s, 6H). 1-56 Cl 4-,[00058] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.77 (s, 1H), 10.16 (s, 1H), 8.96 (d, J = 1.0 Hz, 1H), 7.98 (dd, J = 8.0, 1.0 Hz, 1H), 7.38 (s, 1H), 6.92 (d, J = 8.0 Hz, 1H), 1.91 (s, 6H). 1-57 Cl 2-, F 4-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.12 (s, 1H), 8.21-8.13 (m, 1H), 7.39 (s, 1H), 7.12-7.01 (m, 1H). 1-58 Cl 2-, F 5-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.95 (s, 1H), 8.58-8.38 (m, 1H), 7.86-7.62 (m, 1H), 7.48 (s, 1H). 1-59 Cl 2-, F 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.10 (s, 1H), 8.43-8.28 m, 1H), 7.38 (s, 1H), 7.31- 7.17 (m, 1H). 1-60 Cl 4-, F 5-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.14 (s, 1H), 8.49-8.25 (m, 1H), 7.87-7.66 (m, 1H), 7.41 (s, 1H). 1-61 Cl 4-, F 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.12 (s, 1H), 8.68-8.44 (m, 1H), 7.39 (s, 1H), 7.11-6.98 (m, 1H). 1-62 Cl 5-, F 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.13 (s, 1H), 8.65-8.53 (m, 1H), 8.43-8.31 (m, 1H), 7.39 (s, 1H). 1-63 Cl 2-, Cl 4-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.12 (s, 1H), 7.98 (d, J = 8.0 Hz, 1H), 7.59 (d, J = 7.8 Hz, 1H), 7.39 (s, 1H). 1-64 Cl 2-, Cl 5-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.14 (s, 1H), 8.75 (d, J = 1.0 Hz, 1H), 8.18 (d, J = 1.2 Hz, 1H), 7.40 (s, 1H). 1-65 Cl 2-, Cl 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.09 (s, 1H), 8.57 (d, J = 4.9 Hz, 1H), 7.69 (d, J = 4.9 Hz, 1H), 7.39 (s, 1H). 1-66 Cl 4-, Cl 5-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.14 (s, 1H), 8.87 (d, J = 1.0 Hz, 1H), 8.27 (d, J = 1.2 Hz, 1H), 7.40 (s, 1H). 1-67 Cl 4-, Cl 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.11 (s, 1H), 8.81 (s, 1H), 7.76 (s, 1H), 7.40 (s, 1H). 1-68 Cl 5-, Cl 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.11 (s, 1H), 8.82 (s, 1H), 8.72 (s, 1H), 7.39 (s, 1H). 1-69 Cl 2-, F 4-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.80 (s, 1H), 8.13 (dd, J = 8.0, 4.9 Hz, 1H), 7.56- 7.47 (m, 2H). 1-70 Cl 2-, F 5-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.90 (s, 1H), 8.59-8.41 (m, 1H), 8.32-8.17 (m, 1H), 7.50 (s, 1H). 1-71 Cl 2-, F 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.09 (s, 1H), 8.40-8.31 (m, 1H), 7.60-7.48 (m, 1H), 7.39 (s, 1H). 1-72 Cl 4-, F 5-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.14 (s, 1H), 8.71-8.62 (m, 1H), 8.34-8.22 (m, 1H), 7.40 (s, 1H). 1-73 Cl 4-, F 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.12 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.41-7.33 (m, 2H). 1-74 Cl 5-, F 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.11 (s, 1H), 8.60 (s, 1H), 8.45 (d, J = 10.5 Hz, 1H), 7.42 (s, 1H). 1-75 Cl 2-, Cl 4-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.12 (s, 1H), 8.09 (dd, J = 8.0, 6.5 Hz, 1H), 7.40 (s, 1H), 7.21 (dd, J = 11.5, 8.0 Hz, 1H). 1-76 Cl 2-, Cl 5-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.15 (s, 1H), 8.74 (dd, J = 11.0, 1.3 Hz, 1H), 7.72 (dd, J = 9.5, 1.3 Hz, 1H), 7.40 (s, 1H). 1-77 Cl 2-, Cl 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.10 (s, 1H), 8.60 (dd, J = 6.9, 4.9 Hz, 1H), 7.43- 7.38 (m, 1H), 7.39 (s, 1H). 1-78 Cl 4-, Cl 5-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.14 (s, 1H), 8.65-8.60 (m, 1H), 7.80 (dd, J = 10.0, 1.3 Hz, 1H), 7.40 (s, 1H). 1-79 Cl 4-, Cl 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.11 (s, 1H), 8.85 (d, J = 5.1 Hz, 1H), 7.49 (d, J = 10.9 Hz, 1H), 7.39 (s, 1H). 1-80 Cl 5-, Cl 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.13 (s, 1H), 8.87 (d, J = 4.9 Hz, 1H), 8.70 (d, J = 5.2 Hz, 1H), 7.39 (s, 1H). 1-81 Cl 2-, Me 4-, Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.06 (s, 1H), 7.63 (d, J = 8.0 Hz, 1H), 7.44-7.37 (m, 2H), 2.81 (s, 3H), 2.55 (s, 3H). 1-82 Cl 2-, Me 5-, Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.09 (s, 1H), 8.57 (d, J = 1.3 Hz, 1H), 7.75 (d, J = 1.0 Hz, 1H), 7.39 (s, 1H), 2.80 (s, 3H), 2.27 (s, 3H). 1-83 Cl 4-, Me 5-, Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.92 (s, 1H), 8.99 (d, J = 1.3 Hz, 1H), 7.73 (d, J = 1.3 Hz, 1H), 7.46 (s, 1H), 2.59 (s, 3H), 2.31 (s, 3H). 1-84 Cl 4-, Me 6-, Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.09 (s, 1H), 8.80 (s, 1H), 7.42 (s, 1H), 7.11 (s, 1H), 2.53 (s, 3H), 2.44 (s, 3H). 1-85 Cl 5-, Me 6-, Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.09 (s, 1H), 8.70 (s, 1H), 8.39 (s, 1H), 7.42 (s, 1H), 2.49 (s, 3H), 2.32 (s, 3H). 1-86 Cl 2-, F 4-, Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.98 (s, 1H), 8.00-7.82 (m, 1H), 7.58-7.49 (m, 2H), 2.56 (s, 3H). 1-87 Cl 2-, F 5-, Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.98 (s, 1H), 8.34 (d, J = 5.5 Hz, 1H), 8.08 (dd, J = 7.0, 1.3 Hz, 1H), 7.51 (s, 1H), 2.28 (s, 3H). 1-88 Cl 4-, F 5-, Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.18 (s, 1H), 8.66-8.60 (m, 1H), 8.10-8.01 (m, 1H), 7.39 (s, 1H), 2.30 (s, 3H). 1-89 Cl 4-, F 6-, Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.03 (s, 1H), 8.59 (d, J = 5.9 Hz, 1H), 7.43 (s, 1H), 7.23 (d, J = 10.0 Hz, 1H), 2.47 (s, 3H). 1-90 Cl 2-, Me 4-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.06 (s, 1H), 7.88 (dd, J = 7.9, 5.1 Hz, 1H), 7.42 (s, 1H), 6.97 (dd, J = 11.5, 8.0 Hz, 1H), 2.83 (s, 3H). 1-91 Cl 2-, Cl 4-, Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.19 (s, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.63 (d, J = 8.0 Hz, 1H), 7.41 (s, 1H), 2.55 (s, 3H). 1-92 Cl 2-, Cl 5-, Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.20 (s, 1H), 8.51 (d, J = 1.3 Hz, 1H), 7.92 (d, J = 1.3 Hz, 1H), 7.42 (s, 1H), 2.27 (s, 3H). 1-93 Cl 4-, Cl 6-, Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.04 (s, 1H), 8.76 (s, 1H), 7.42 (s, 1H), 7.40 (s, 1H), 2.46 (s, 3H). 1-94 Cl 4-, Cl 5-, Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.17 (s, 1H), 8.83 (d, J = 1.3 Hz, 1H), 8.03 (d, J = 1.3 Hz, 1H), 7.39 (s, 1H), 2.32 (s, 3H). 1-95 Cl 2-, Me 4-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.10 (s, 1H), 7.80 (d, J = 8.0 Hz, 1H), 7.41(d, J = 8.0 Hz, 1H), 7.32 (s, 1H), 2.84 (s, 3H). 1-96 Cl 4-, Br 5-, Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.01 (s, 1H), 8.64 (d, J = 1.3 Hz, 1H), 7.95 (d, J = 1.3 Hz, 1H), 7.43 (s, 1H), 2.28 (s, 3H). 1-97 Cl 2-, Cl 4-, CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.14 (s, 1H), 7.95 (d, J = 7.8 Hz, 1H), 7.83 (d, J = 7.8 Hz, 1H), 7.40 (s, 1H). 1-98 Cl 4-, Cl 5-, CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.15 (s, 1H), 8.99 (d, J = 1.3 Hz, 1H), 8.31 (d, J = 1.3 Hz, 1H), 7.40 (s, 1H). 1-99 Cl 2-, Cl 5-, CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.15 (s, 1H), 8.75 (s, 1H), 8.18 (s, 1H), 7.40 (s, 1H). 1-100 Cl 4-, Cl 6-, CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.12 (s, 1H), 8.88 (s, 1H), 7.71 (s, 1H), 7.40 (s, 1H). 1-101 Cl 2-,[00059]4-,[00060] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.05 (s, 1H), 7.70 (d, J = 8.0 Hz, 1H), 7.49 (s, 1H), 6.38 (d, J = 8.0 Hz, 1H), 4.06 (s, 3H), 3.89 (s, 3H). 1-102 Cl 4-,[00061]5-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.18 (s, 1H), 9.11 (d, J = 1.3 Hz, 1H), 8.08 (d, J = 1.3 Hz, 1H), 7.39 (s, 1H), 3.31 (hept, J = 7.0 Hz, 1H), 1.22 (d, J = 6.7 Hz, 6H). 1-103 Cl 4-, COOMe 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.11 (s, 1H), 9.12 (s, 1H), 8.38 (s, 1H), 7.40 (s, 1H), 3.90 (s, 3H). 1-104 Cl 4-,[00062]5-, NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.16 (s, 1H), 8.13 (d, J = 1.3 Hz, 1H), 7.39 (s, 1H), 6.81 (d, J = 1.3 Hz, 1H), 5.44 (s, 2H), 3.83 (s, 3H). 1-105 Cl 2-, F 4-, F 5-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.66 (s, 1H), 8.07-7.81 (m, 1H), 7.57 (s, 1H). 1-106 Cl 2-, F 4-, F 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.06 (s, 1H), 7.40 (s, 1H), 7.10-6.88 m, 1H). 1-107 Cl 2-, F 5-, F 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.08 (s, 1H), 8.56-8.30 (m, 1H), 7.40 (s, 1H). 1-108 Cl 4-, F 5-, F 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.16 (s, 1H), 8.45-8.18 (m, 1H), 7.40 (s, 1H). 1-109 Cl 2-, Cl 4-, Cl 5-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.12 (s, 1H), 8.32 (s, 1H), 7.40 (s, 1H). 1-110 Cl 2-, Cl 4-, Cl 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.10 (s, 1H), 7.85 (s, 1H), 7.39 (s, 1H). 1-111 Cl 2-, Cl 5-, Cl 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.10 (s, 1H), 8.77 (s, 1H), 7.39 (s, 1H). 1-112 Cl 4-, Cl 5-, Cl 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.10 (s, 1H), 8.77 (s, 1H), 7.40 (s, 1H). 1-113 Cl 2-, F 4-, F 5-, F 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.11 (s, 1H), 7.40 (s, 1H). 1-114 Cl 2-, Cl 4-, Cl 5-, Cl 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.20 (s, 1H), 7.39 (s, 1H). 1-115 Cl 2-,[00063]4-, Me 5-, Me 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.05 (s, 1H) 7.39 (s, 1H), 6.56 (d, J = 10.8 Hz, 1H), 5.71 (dq, J = 10.9, 6.4 Hz, 1H), 2.62 (s, 3H), 2.33 (s, 3H), 1.72 (dd, J = 6.5 Hz, 3H). 1-116 Me 4-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.88 (s, 1H), 8.68 (dd, J = 5.5, 1.4 Hz, 1H), 8.00- 7.82 (m, 1H), 7.14-7.01 (m, 1H), 6.82 (s, 1H), 2.22 (s, 3H). 1-117 Me 4-,[00064] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.96 (s, 1H), 9.57 (s, 1H), 9.12 (d, J = 1.3 Hz, 1H), 8.39 (d, J = 8.0 Hz, 1H), 8.22 (dd, J = 7.9, 1.2 Hz, 1H), 6.80 (s, 1H), 2.22 (s, 3H), 1.49 (s, 9H). 1-118 Me 2-,[00065]5-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.87 (s, 1H), 8.59-8.33 (m, 1H), 7.51-7.39 (m, 1H), 6.97 (s, 1H), 4.04 (s, 2H), 2.22 (s, 3H), 1.90 (s, 3H). 1-119 Et 4-, CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.18 (s, 1H), 9.20 (d, J = 1.3 Hz, 1H), 8.29 (dd, J = 7.9, 1.2 Hz, 1H), 7.78 (d, J = 7.9 Hz, 1H), 6.78 (s, 1H), 2.60 (q, J = 8.0 Hz, 2H), 1.15 (t, J = 8.0 Hz, 3H). 1-120 Et 4-,[00066] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.97 (s, 1H), 9.12 (d, J = 1.4 Hz, 1H), 8.56 (s, 1H), 8.14 (dd, J = 7.9, 1.2 Hz, 1H), 7.94 (s, 1H), 7.30 (d, J = 8.0 Hz, 1H), 6.85 (s, 1H), 2.71 (s, 3H), 2.60 (q, J = 8.0 Hz, 2H), 1.16 (t, J = 8.0 Hz, 3H). 1-121 Et 4-,[00067]6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.11 (s, 1H), 9.05 (s, 1H), 8.34 (s, 1H), 6.82 (s, 1H), 3.26 (q, J = 8.0 Hz, 2H), 2.60 (q, J = 8.0 Hz, 2H), 1.21 (t, J = 7.9 Hz, 3H), 1.15 (t, J = 8.0 Hz, 3H). 1-122 CN 5-, NH.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.19 (s, 1H), 8.42 (d, J = 1.3 Hz, 1H), 8.07 (s, 1H), 7.86 (s, 1H), 7.31 (d, J = 1.3 Hz, 1H), 6.17 (s, 2H). 1-123 CN 5-, NO.sub.2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.21 (s, 1H), 9.57 (d, J = 1.4 Hz, 1H), 9.26 (s, 1H), 8.97 (d, J = 1.3 Hz, 1H), 7.88 (s, 1H). 1-124 CN 2-,[00068] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.50 (s, 1H), 9.10 (s, 1H), 8.32 (dd, J = 5.2, 1.3 Hz, 1H), 7.97 (s, 1H), 7.77 (dd, J = 8.0, 1.3 Hz, 1H), 7.30 (dd, J = 8.0, 4.9 Hz, 1H), 3.77 (s, 2H), 3.31 (q, J = 8.0 Hz, 2H), 2.90 (s, 3H), 1.17 (t, J = 8.0 Hz, 3H). 1-125 CN 5-,[00069] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.03 (s, 1H), 9.94 (s, 1H), 8.70-8.63 (m, 2H), 8.14 (s, 1H), 7.93 (s, 1H), 2.07 (s, 3H). 1-126 CN 5-,[00070] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.93 (s, 1H), 9.03-8.90 (m, 2H), 8.30-8.22 (m, 1H), 7.95 (s, 1H), 7.88 (s, 1H), 2.89 (s, 3H). 1-127 CN 2-, Et 5-,[00071] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.09 (s, 1H), 8.90 (d, J = 1.0 Hz, 1H), 7.96 (d, J = 1.3 Hz, 1H), 7.87 (s, 1H), 5.09 (s, 2H), 2.85 (q, J = 8.0 Hz, 2H), 2.09 (s, 3H), 1.15 (t, J = 7.9 Hz, 3H). 1-128 F 6-,[00072] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.77 (s, 1H), 8.57 (s, 1H), 7.97 (s, 1H), 7.58 (d, J = 5.2 Hz, 1H), 7.45 (d, J = 5.2 Hz, 1H), 5.13 (s, 2H), 2.94 (q, J = 8.0 Hz, 2H), 1.34 (t, J = 8.0 Hz, 3H). 1-129 Br 4-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.02 (s, 1H), 8.70 (dd, J = 5.5, 1.2 Hz, 1H), 8.00- 7.88 (m, 1H), 7.67 (s, 1H), 7.14-7.02 (m, 1H). 1-130 Br 2-, F 5-,[00073] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.13 (s, 1H), 8.58 (dd, J = 5.5, 1.3 Hz, 1H), 8.02 (dd, J = 4.9, 1.3 Hz, 1H), 7.62 (s, 1H), 6.74 (d, J = 15.0 Hz, 1H), 6.64 (d, J = 15.0 Hz, 1H). 1-131 CF.sub.2CF.sub.3 2-, F 4-, F .sup.1H NMR (500 MHz, Chloroform-d) 8.44- 8.30 (m, 1H), 7.34 (s, 1H), 6.99-6.80 (m, 1H), 5.11 (s, 1H). 1-132 CF.sub.2CF.sub.3 2-,[00074] 1-133 CF.sub.2CF.sub.3 2-, F 5-, CH.sub.2CF.sub.3 1-134 CHF.sub.2 4-,[00075] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.99 (s, 1H), 8.75 (d, J = 1.3 Hz, 1H), 7.89 (dd, J = 8.0, 1.3 Hz, 1H), 7.43-7.33 (m, 4H), 7.35- 7.27 (m, 1H), 7.18 (d, J = 7.9 Hz, 1H), 7.01 (s, 1H), 6.68 (t, J = 73.5 Hz, 1H), 5.32 (s, 2H). 1-135 CF.sub.2CF.sub.3 2-, F 4-,[00076] 1-136 CHF.sub.2 2-, F 1-137 CH.sub.2F 4-,[00077] 1-138 CH.sub.2F 2-,[00078]5-, Cl 6-, Cl 1-139 [00079] 4-, CF.sub.3 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.23 (s, 1H), 9.31 (d, J = 1.4 Hz, 1H), 8.41 (dd, J = 8.0, 1.3 Hz, 1H), 7.90 (d, J = 8.0 Hz, 1H), 7.81 (d, J = 7.3 Hz, 2H), 7.71-7.62 (m, 3H). 1-140 OMe 4-, Ph 5-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.17 (s, 1H), 8.85-8.78 (m, 1H), 8.05-7.99 (m, 2H), 7.68-7.54 (m, 1H), 7.55-7.43 (m, 3H), 6.94 (s, 1H), 3.84 (s, 3H). 1-141 OMe 4-, SO.sub.2Me 5-, Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.15 (s, 1H), 9.02 (d, J = 1.3 Hz, 1H), 8.11 (d, J = 1.3 Hz, 1H), 6.92 (s, 1H), 3.84 (s, 3H), 3.26 (s, 3H), 2.38 (s, 3H). 1-142 OEt 2-,[00080] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.42 (s, 1H), 8.78 (dd, J = 4.9, 1.3 Hz, 1H), 7.81 (dd, J = 8.0, 4.9 Hz, 1H), 7.75 (dd, J = 8.0, 1.3 Hz, 1H), 7.21-7.13 (m, 1H), 7.14- 6.99 (m, 4H), 6.93 (s, 1H), 4.66 (s, 2H), 4.39 (q, J = 6.0 Hz, 2H), 1.36 (t, J = 5.8 Hz, 3H). 1-143 OEt 4-, F 5-, Ph .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.10 (s, 1H), 8.91-8.80 (m, 1H), 8.69-8.52 (m, 1H), 7.69-7.62 (m, 2H), 7.47-7.35 (m, 3H), 6.96 (s, 1H), 4.39 (q, J = 6.0 Hz, 2H), 1.36 (t, J = 5.8 Hz, 3H). 1-144 OCH.sub.2F 4-,[00081] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.16 (s, 1H), 9.04 (d, J = 1.4 Hz, 1H), 7.90 (dd, J = 8.0, 1.3 Hz, 1H), 7.49 (d, J = 8.0 Hz, 1H), 6.97 (s, 1H), 6.79 (d, J = 68.0 Hz, 1H), 2.33 (s, 3H). 1-145 OCHF.sub.2 5-,[00082] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.14 (s, 1H), 8.98 (d, J = 1.4 Hz, 1H), 8.70 (d, J = 1.2 Hz, 1H), 7.86 (t, J = 1.2 Hz, 1H), 7.34 (s, 1H), 6.96 (t, J = 73.0 Hz, 1H), 4.37 (s, 2H), 2.28 (s, 3H). 1-146 OCF.sub.3 4-, CF.sub.3 6-,[00083] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.94 (s, 1H), 8.91 (s, 1H), 7.94 (s, 1H), 7.03 (s, 1H), 5.52 (s, 2H), 3.30 (s, 3H). 1-147 OCF.sub.2CF.sub.3 4-,[00084] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.12 (s, 1H), 8.66 (d, J = 1.4 Hz, 1H), 7.87 (dd, J = 8.0, 1.3 Hz, 1H), 7.04 (d, J = 8.0 Hz, 1H), 6.95 (s, 1H), 4.68 (t, J = 7.2 Hz, 2H), 3.83 (t, J = 7.2 Hz, 2H), 3.33 (s, 3H). 1-148 [00085] 5-,[00086] .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.90 (s, 1H), 8.74 (d, J = 1.3 Hz, 1H), 8.44 (d, J = 1.3 Hz, 1H), 7.87 (t, J = 1.2 Hz, 1H), 6.86 (s, 1H), 3.86 (s, 2H), 2.92 (t, J = 5.6 Hz, 2H), 2.77 (t, J = 5.6 Hz, 2H), 2.44 (t, J = 5.5 Hz, 2H), 2.22 (s, 3H), 1.56- 1.44 (m, 2H), 0.89 (t, J = 8.0 Hz, 3H). 1-149 [00087] 4-,[00088]6-, Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.09 (s, 1H), 8.28 (s, 1H), 6.85 (s, 1H), 6.50 (s, 1H), 3.03 (hept, J = 6.8 Hz, 1H), 2.46 (s, 3H), 2.08 (s, 3H), 1.23 (d, J = 6.7 Hz, 6H). 1-150 Cl 4-,[00089] 1-151 Cl 5-,[00090] 1-152 Cl 4-,[00091] 1-153 Cl 2-,[00092] 1-154 Br 6-,[00093] 1-155 Cl 4-,[00094] 1-156 Cl 4-,[00095] 1-157 OMe 4-,[00096] 1-158 Cl 5-,[00097] 1-159 Cl 4-,[00098] 1-160 Cl 4-,[00099] 1-161 Cl 6-,[00100] 1-162 Cl 4-,[00101] 1-163 Cl 2-,[00102] 1-164 Cl 4-,[00103] 1-165 Cl 4-,[00104] 1-166 Cl 5-,[00105] 1-167 Cl 4-,[00106] 1-168 CF.sub.3 6-, CHF.sub.2 1-169 CF.sub.3 2-, Me 4-,[00107] 1-170 CF.sub.3 4-,[00108]6, -OMe 1-171 CF.sub.3 5-,[00109] 1-172 CF.sub.3 5-,[00110] 1-173 CF.sub.3 4-,[00111] 1-174 CF.sub.3 2-, Cl 6-,[00112]

TABLE-US-00002 TABLE 2 Structure and .sup.1HNMR data of Compound (2) (2) [00113] No. X Y .sup.1H NMR 2-1 Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.17 (s, 1H), 8.66 (d, J = 5.3 Hz, 2H), 7.91 (d, J = 5.0 Hz, 2H), 7.39 (s, 1H). 2-2 Cl 2, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.05 (s, 1H), 8.51- 8.45 (m, 2H), 7.77-7.75 (m, 1H), 7.50 (s, 1H). 2-3 Cl 3, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.96 (s, 1H), 8.43- 8.33 (m, 1H), 7.87-7.81 (m, 1H), 7.74-7.69 (m, 1H), 7.46 (s, 1H). 2-4 Cl 2, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.18 (s, 1H), 8.76- 8.68 (m, 2H), 7.78 (d, J = 5.0 Hz, 1H), 7.42 (s, 1H). 2-5 Cl 3, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.97 (s, 1H), 8.44 (d, J = 5.2 Hz, 1H), 8.25 (d, J = 1.0 Hz, 1H), 7.81 (dd, J = 4.9, 1.0 Hz, 1H), 7.45 (s, 1H). 2-6 Cl 2, Br .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.09 (s, 1H), 8.80 (d, J = 4.9 Hz, 1H), 8.74 (s, 1H), 7.85 (d, J = 5.1 Hz, 1H), 7.43 (s, 1H). 2-7 CF.sub.3 3, Br .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.95 (s, 1H), 8.14 (d, J = 5.1 Hz, 1H), 8.03 (d, J = 1.1 Hz, 1H), 7.80 (dd, J = 5.2, 1.0 Hz, 1H), 7.45 (s, 1H). 2-8 CF.sub.3 2, I .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.05 (s, 1H), 8.88 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.52 (d, J = 5.1 Hz, 1H), 7.44 (s, 1H). 2-9 Cl 3, I .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.94 (s, 1H), 8.25 (d, J = 5.0 Hz, 1H), 8.13 (d, J = 1.0 Hz, 1H), 7.68 (dd, J = 4.9, 1.0 Hz, 1H), 7.45 (s, 1H). 2-10 Cl 2-, F 3-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.13 (s, 1H), 8.18- 8.02 (m, 1H), 7.69-7.53 (m, 1H), 7.39 (s, 1H). 2-11 Cl 2-, F 5-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.13 (s, 1H), 8.62- 8.51 (m, 1H), 7.80-7.65 (m, 1H), 7.39 (s, 1H). 2-12 Cl 2-, F 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.85 (s, 1H), 8.23 (d, J = 10.0 Hz, 2H), 7.47 (s, 1H). 2-13 Cl 3-, F 5-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.20 (s, 1H), 7.86 (d, J = 7.8 Hz, 2H), 7.40 (s, 1H). 2-14 Cl 3-, F 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.13 (s, 1H) 8.62- 6.45 (m, 1H), 7.80-7.63 (m, 1H), 7.39 (s, 1H). 2-15 Cl 2-, Cl 3-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.12 (s, 1H), 8.41 (d, J = 4.9 Hz, 1H), 7.85 (d, J = 4.9 Hz, 1H), 7.39 (s, 1H). 2-16 Cl 2-, Cl 5-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.11 (s, 1H), 8.80 (s, 1H), 8.28 (s, 1H), 7.40 (s, 1H). 2-17 Cl 2-, Cl 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.10 (s, 1H) ,8.72 (s, 2H), 7.39 (s, 1H). 2-18 Cl 3-, Cl 5-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.19 (s, 1H), 8.36 (s, 2H), 7.40 (s, 1H). 2-19 Cl 3-, Cl 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.11 (s, 1H), 8.80 (s, 1H), 8.28 (s, 1H), 7.40 (s, 1H). 2-20 Cl 2-, F 3-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.13 (s, 1H), 8.19- 8.10 (m, 1H), 7.79-7.56 (m, 1H), 7.39 (s, 1H). 2-21 Cl 2-, F 5-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.12 (s, 1H), 8.78 (d, J = 7.9 Hz, 1H), 8.21 (d, J = 5.0 Hz, 1H), 7.39 (s, 1H). 2-22 Cl 2-, F 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.09 (s, 1H), 8.50 (s, 1H), 8.45 (d, J = 7.9 Hz, 1H), 7.39 (s, 1H). 2-23 Cl 3-, F 5-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.19 (s, 1H), 8.27 (d, J = 1.0 Hz, 1H), 7.96 (dd, J = 8.0, 1.0 Hz, 1H), 7.40 (s, 1H). 2-24 Cl 3-, F 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.12 (s, 1H), 8.63 (s, 1H), 7.87 (d, J = 7.9 Hz, 1H), 7.40 (s, 1H). 2-25 Cl 2-, Cl 3-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.13 (s, 1H), 8.40- 8.24 (m, 1H), 7.77-7.61 (m, 1H), 7.40 (s, 1H). 2-26 Cl 2-, Cl 5-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.12 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.87 (d, J = 8.0 Hz, 1H), 7.40 (s, 1H). 2-27 Cl 2-, Cl 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.09 (s, 1H), 8.50 (s, 1H), 8.45 (d, J = 9.9 Hz, 1H), 7.39 (s, 1H). 2-28 Cl 3-, Cl 5-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.19 (s, 1H), 8.27 (d, J = 1.0 Hz, 1H), 7.99-7.93 (m, 1H), 7.40 (s, 1H). 2-29 Br 3-, Cl 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.13 (s, 1H), 8.78 (d, J = 8.0 Hz, 1H), 8.20 (d, J = 5.0 Hz, 1H), 7.62 (s, 1H). 2-30 Cl 2-, F 3-, F 5-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.82 (s, 1H), 7.82- 7.59 (m, 1H), 7.53 (s, 1H). 2-31 Cl 2-, F 3-, F 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.07 (s, 1H), 8.36- 8.17 (m, 1H), 7.40 (s, 1H). 2-32 Cl 2-, F 5-, F 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.05 (s, 1H), 8.36- 8.14 (m, 1H), 7.41 (s, 1H). 2-33 Cl 3-, F 5-, F 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.96 (s, 1H), 7.80- 7.60 (m, 1H), 7.48 (s, 1H). 2-34 Cl 2-, Cl 3-, Cl 5-, .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.12 (s, 1H), 8.35 (s, Cl 1H), 7.40 (s, 1H). 2-35 Cl 2-, Cl 3-, Cl 6-, .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.11 (s, 1H), 8.77 (s, Cl 1H), 7.40 (s, 1H). 2-36 Cl 2-, Cl 5-, Cl 6-, .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.11 (s, 1H), 8.77 (s, Cl 1H), 7.40 (s, 1H). 2-37 Cl 3-, Cl 5-, Cl 6-, .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.12 (s, 1H), 8.35 (s, Cl 1H), 7.40 (s, 1H). 2-38 Cl 2-, F 3-, F 5-, F .sup.1H NMR( 500 MHz, DMSO-d.sub.6) 13.14 (s, 1H), 7.40 (s, 6-, F 1H). 2-39 Cl 2-, Cl 3-, Cl 5-, .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.11 (s, 1H), 7.40 (s, Cl 6-, Cl 1H). 2-40 Cl 3-, Me .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.95 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 7.61-7.52 (m, 2H), 7.46 (s, 1H), 2.50 s, 3H). 2-41 Cl 3-, OMe .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.17 (s, 1H), 8.10 (d, J = 4.9 Hz, 1H), 7.45 (d, J = 1.1 Hz, 1H), 7.39 (s, 1H), 7.13 (dd, J = 4.9, 1.0 Hz, 1H), 3.89 (s, 3H). 2-42 Cl [00114] 2-43 Cl [00115] 2-44 Cl 3-, CF.sub.3 2-45 Br 2-, Me 5-, F 2-46 Cl 2-, Me 3-, Cl 2-47 Me 2-, Me 3-, F 2-48 Cl 2-, Me 5-, Cl 2-49 CN 2-, Me 6-, F 2-50 Cl 2-, Me 6-, Cl 2-51 Cl 3-, Me 5-, F 2-52 Cl 3-, Me 6-, Cl 2-53 Cl 3-, Me 5-, Cl 2-54 CF.sub.2CF.sub.3 3-, Me 6-, F 2-55 Cl 5-, Me 6-, F 2-56 F 50, Me 6-, Cl 2-57 Cl [00116] 2-58 Cl 2-, CN 2-59 Et 2-, NH.sub.2 2-60 Cl 2-, OMe 5-, OMe 2-61 Cl 3-, OEt 2-62 Cl 3-, NH.sub.2 6-, OMe 2-63 Cl 5-, Me 3-, Br 2-64 OMe 2-, Me 3-, Me 2-65 Cl 3-, Me 5-, Me 2-66 Cl 2-, Me 5-, Me 2-67 OCF.sub.3 2-, Me 6-, Me 2-68 Cl 3-, N.sub.3 2-69 Cl [00117] 2-70 Cl [00118] 2-71 Cl [00119] 2-72 Cl [00120] 2-73 Cl [00121] 2-74 Cl [00122] 2-75 Cl [00123] 2-76 Cl [00124] 2-77 Cl [00125] 2-78 Cl [00126] 2-79 Cl [00127] 2-80 Cl [00128] 2-81 Cl [00129] 2-82 Cl [00130] 2-83 Cl [00131] 2-84 Cl [00132] 2-85 Cl [00133] 2-86 Cl [00134] 2-87 Cl [00135] 2-88 Cl [00136] 2-89 Cl [00137] 2-90 Cl [00138] 2-91 Cl [00139] 2-92 Cl [00140] 2-93 Cl [00141] 2-94 Cl [00142] 2-95 Cl [00143] 2-96 Cl [00144] 2-97 Cl [00145] 2-98 Cl [00146] 2-99 Cl [00147] 2-100 CH.sub.2F [00148] 2-101 Cl [00149] 2-102 Cl [00150] 2-103 Cl [00151] 2-104 Cl [00152] 2-105 Cl [00153] 2-106 Cl [00154] 2-107 Cl [00155] 2-108 Br [00156] 2-109 Cl [00157] 2-110 Cl [00158] 2-111 Cl [00159] 2-112 Cl [00160] 2-113 Me [00161] 2-114 Cl [00162] 2-115 Cl [00163] 2-116 Cl [00164] 2-117 Cl [00165] 2-118 Cl [00166] 2-119 Cl [00167] 2-120 Cl [00168] 2-121 CHF.sub.2 [00169] 2-122 Cl [00170] 2-123 Cl [00171] 2-124 CF.sub.3 [00172] 2-125 CF.sub.3 [00173] 2-126 CF.sub.3 2-, Me 6-, CF.sub.3 2-127 CF.sub.3 3-, OEt 2-128 CF.sub.3 [00174]

TABLE-US-00003 TABLE 3 Structure and .sup.1HNMR data of Compound (3) (3) [00175] No. X Y .sup.1H NMR 3-1 Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.42 (s, 1H), 8.75-8.73 (m, 1H), 8.21-8.19 (m, 1H), 8.04-8.00 (m, 1H), 7.60-7.58 (m, 1H), 7.27 (s, 1H). 3-2 Cl 3-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.18 (s, 1H), 8.19- 8.04 (m, 1H), 7.86-7.82 (m, 1H), 7.28 (s, 1H), 7.04-7.00 (m, 1H). 3-3 Cl 4-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.28 (s, 1H), 8.83 (dd, J = 8.0, 1.2 Hz, 1H), 7.92 (dd, J = 8.0, 5.1 Hz, 1H), 7.76-7.73 (m, 1H), 7.27 (s, 1H). 3-4 Cl 5-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.36 (s, 1H), 8.68- 8.45 (m, 1H), 7.59-7.43 (m, 1.0 Hz, 1H), 7.32- 7.25 (m, 2H). 3-5 Cl 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.47 (s, 1H), 8.42 (dd, J = 5.0, 1.2 Hz, 1H), 7.76-7.73 (m, 1H), 7.56-7.52 (m, 1H), 7.27 (s, 1H). 3-6 Cl 3-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.22 (s, 1H), 8.31- 8.26 (m, 1H), 7.91-7.88 (m, 1H), 7.67-7.61 (m, 1H), 7.28 (s, 1H). 3-7 Cl 4-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.28 (s, 1H), 8.84 (d, J = 1.2 Hz, 1H), 7.99 (d, J = 8.0 Hz, 1H), 7.85 (dd, J = 8.0, 1.0 Hz, 1H), 7.27 (s, 1H). 3-8 Cl 5-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.35 (s, 1H), 8.66 (d, J = 4.9, Hz, 1H), 7.89 (d, J = 1.1 Hz, 1H), 7.60- 7.55 (m, 1H), 7.28 (s, 1H). 3-9 Cl 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.98 (s, 1H), 8.64 (dd, J = 4.9, 1.3 Hz, 1H), 7.85 (dd, J = 8.0, 1.3 Hz, 1H), 7.61 (dd, J = 8.0, 4.9 Hz, 1H), 7.29 (s, 1H). 3-10 Cl 3-, Br .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.23 (s, 1H), 8.28 (dd, J = 8.0, 1.0 Hz, 1H), 7.65-7.62 (m, 1H), 7.48 (dd, J = 7.0, 1.0 Hz, 1H), 7.28 (s, 1H). 3-11 Cl 4-, Br .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.29 (s, 1H), 8.96 (d, J = 1.3 Hz, 1H), 8.21 (dd, J = 7.9, 1.2 Hz, 1H), 8.04 (d, J = 8.0 Hz, 1H), 7.27 (s, 1H). 3-12 Cl 5-, Br .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.34 (s, 1H), 8.67 (d, J = 4.9 Hz, 1H), 8.09 (d, J = 1.1 Hz, 1H), 7.70 (dd, J = 5.2, 1.0 Hz, 1H), 7.27 (s, 1H). 3-13 CF.sub.3 6-, Br .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.78 (s, 1H), 8.73 (dd, J = 5.1, 1.3 Hz, 1H), 7.98 (dd, J = 8.0, 1.3 Hz, 1H), 7.66 (dd, J = 7.9, 5.1 Hz, 1H), 7.29 (s, 1H). 3-14 Cl 3-, I .sup.1H NMR( 500 MHz, DMSO-d.sub.6) 13.24 (s, 1H), 8.17 (dd, J = 8.0, 1.0 Hz, 1H), 7.76 (dd, J = 8.0, 1.0 Hz, 1H), 7.54-7.51 (m, 1H), 7.27 (s, 1H). 3-15 CF.sub.3 4-, I .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.29 (s, 1H), 9.21 (d, J = 1.1 Hz, 1H), 8.22 (dd, J = 7.9, 1.2 Hz, 1H), 7.67 (d, J = 8.0 Hz, 1H), 7.27 (s, 1H). 3-16 Cl 5-, I .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.34 (s, 1H), 8.43 (d, J = 5.0 Hz, 1H), 8.25 (d, J = 1.0 Hz, 1H), 7.92 (dd, J = 4.9, 1.0 Hz, 1H), 7.27 (s, 1H). 3-17 Cl 6-, I .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.45 (s, 1H), 8.62 (dd, J = 4.9, 1.3 Hz, 1H), 8.22 (dd, J = 8.0, 1.3 Hz, 1H), 7.30 (s, 1H), 7.19 (dd, J = 8.0, 5.2 Hz, 1H). 3-18 Cl 3-, F 4-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.06 (s, 1H), 7.97-7.90 (m, 2H), 7.28 (s, 1H). 3-19 Cl 3-, F 5-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.12 (s, 1H), 7.60 (dd, J = 8.0, 1.0 Hz, 1H), 7.28 (s, 1H), 7.10-7.07 (m, 1H). 3-20 Cl 3-, F 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.24 (s, 1H), 7.97- 7.82 (m, 1H), 7.28 (s, 1H), 7.14-7.01 (m, 1H). 3-21 Cl 4-, F 5-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.22 (s, 1H), 8.83 (dd, J = 8.1, 4.9 Hz, 1H), 7.57 (dd, J = 10.0, 6.5 Hz, 1H), 7.28 (s, 1H). 3-22 Cl 4-, F 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.33 (s, 1H), 8.61- 8.47 (m, 1H), 7.65-7.47 (m, 1H), 7.27 (s, 1H). 3-23 Cl 5-, F 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.42 (s, 1H), 8.45 (dd, J = 6.5, 5.1 Hz, 1H), 7.30-7.22 (m, 2H). 3-24 Cl 3-, Cl 4-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.09 (s, 1H), 8.07 (d, J = 8.0 Hz, 1H), 7.99 (d, J = 8.0 Hz, 1H), 7.28 (s, 1H). 3-25 Cl 3-, Cl 5-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.14 (s, 1H), 7.99 (d, J = 1.0 Hz, 1H), 7.74 (d, J = 1.0 Hz, 1H), 7.28 (s, 1H). 3-26 Cl 3-, Cl 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.75 (s, 1H), 7.95 (d, J = 7.8 Hz, 1H), 7.58 (d, J = 8.0 Hz, 1H), 7.30 (s, 1H). 3-27 Cl 4-, Cl 5-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.20 (s, 1H), 8.86 (s, 1H), 8.00 (s, 1H), 7.28 (s, 1H). 3-28 Cl 4-, Cl 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.80 (s, 1H), 8.82 (d, J = 1.2 Hz, 1H), 8.06 (d, J = 1.3 Hz, 1H), 7.29 (s, 1H). 3-29 Cl 5-, Cl 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.58 (s, 1H), 8.63 (d, J = 5.2 Hz, 1H), 7.67 (d, J = 5.2 Hz, 1H), 7.30 (s, 1H). 3-30 Cl 3-, F 4-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.06 (s, 1H), 8.06 (dd, J = 8.0, 4.9 Hz, 1H), 7.98 (d, J = 7.9 Hz, 1H), 7.28 (s, 1H). 3-31 Cl 3-, F 5-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.11 (s, 1H), 7.89 (d, J = 1.0 Hz, 1H), 7.38 (dd, J = 10.0, 1.0 Hz, 1H), 7.28 (s, 1H). 3-32 Cl 3-, F 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.70 (s, 1H), 8.07 (dd, J = 7.9, 5.1 Hz, 1H), 7.30 (s, 1H), 7.21 (dd, J = 10.0, 8.0 Hz, 1H). 3-33 Cl 4-, F 5-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.20 (s, 1H), 8.85 (d, J = 8.0 Hz, 1H), 7.88 (d, J = 4.9 Hz, 1H), 7.28 (s, 1H). 3-34 Cl 4-, F 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.80 (s, 1H), 8.82 (dd, J = 8.0, 1.3 Hz, 1H), 7.68 (dd, J = 10.0, 1.3 Hz, 1H), 7.29 (s, 1H). 3-35 Cl 5-, F 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.83 (s, 1H), 8.66 (dd, J = 6.5, 5.1 Hz, 1H), 7.38 (dd, J = 10.0, 4.9 Hz, 1H), 7.29 (s, 1H). 3-36 Cl 3-, Cl 4-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.09 (s, 1H), 8.01 (dd, J = 8.0, 4.9 Hz, 1H), 7.88 (dd, J = 11.5, 8.0 Hz, 1H), 7.28 (s, 1H). 3-37 Cl 3-, Cl 5-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.15 (s, 1H), 7.69 (dd, J = 8.0, 1.0 Hz, 1H), 7.46 (dd, J = 8.0, 1.0 Hz, 1H), 7.28 (s, 1H). 3-38 Cl 3-, Cl 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.27 (s, 1H), 7.86 (dd, J = 11.5, 8.0 Hz, 1H), 7.51 (dd, J = 8.0, 5.9 Hz, 1H), 7.27 (s, 1H). 3-39 Cl 4-, Cl 5-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.22 (s, 1H), 8.84 (d, J = 5.0 Hz, 1H), 7.70 (d, J = 11.0 Hz, 1H), 7.28 (s, 1H). 3-40 Cl 4-, Cl 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.33 (s, 1H), 8.61 (d, J = 1.3 Hz, 1H), 7.68 (dd, J = 11.0, 1.2 Hz, 1H), 7.27 (s, 1H). 3-41 Cl 5-, Cl 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.42 (s, 1H), 8.42 (d, J = 5.2 Hz, 1H), 7.55 (dd, J = 7.5, 5.1 Hz, 1H), 7.27 (s, 1H). 3-42 Cl 3-, F 4-, F 5-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.99 (s, 1H), 7.59- 7.35 (m, 1H), 7.29 (s, 1H). 3-43 Cl 3-, F 4-, F 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.11 (s, 1H), 7.88- 7.52 (m, 1H), 7.28 (s, 1H). 3-44 Cl 3-, F 5-, F 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.18 (s, 1H), 7.28 (s, 1H), 7.08-6.86 (m, 1H). 3-45 Cl 4-, F 5-, F 6-, F .sup.1H NMR (500 MHz, DMSO-d.sub.6) 10.06 (s, 1H), 8.58- 8.31 (m, 1H), 7.26 (s, 1H). 3-46 Cl 3-, Cl 4-, Cl 5-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.01 (s, 1H), 8.09 (s, 1H), 7.28 (s, 1H). 3-47 Br 3-, Cl 4-, Cl 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.58 (s, 1H), 8.22 (s, 1H), 7.30 (s, 1H). 3-48 Cl 3-, Cl 5-, Cl 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.33 (s, 1H), 7.84 (s, 1H), 7.31 (s, 1H). 3-49 Cl 4-, Cl, 5-, Cl 6-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.31 (s, 1H), 8.84 (s, 1H), 7.31 (s, 1H). 3-50 Cl 3-, F 4-, F 5-, F 6-, .sup.1H NMR (500 MHz, DMSO-d.sub.6) 13.06 (s, 1H), 7.26 F (s, 1H). 3-51 Cl 3-, Cl 4-, Cl 5-, Cl .sup.1H NMR (500 MHz, DMSO-d.sub.6) 12.07 (s, 1H), 7.32 6-, Cl (s, 1H). 3-52 Cl 4-, 5-, together forms CHCHCHCH 3-53 Cl 3-, Me 3-54 Cl 3-, OMe 3-55 Cl [00176] 3-56 Br [00177] 3-57 Cl 3-, CF.sub.3 3-58 Cl 3-, Me 4-, F 3-59 Cl 3-, Me 4-, Cl 3-60 Br 3-, Me 5-, F 3-61 Cl 3-, Me 5-, Cl 3-62 Cl 3-, Me 6-, F 3-63 Me 3-, Me 6-, Cl 3-64 Cl 4-, Me 5-, F 3-65 Cl 4-, Me 5-, Cl 3-66 CN 4-, Me 6-, Cl 3-67 Cl 4-, Me 6-, F 3-68 Cl 5-, Me 6-, F 3-69 Cl 5-, Me 6-, Cl 3-70 Cl [00178] 3-71 Cl 4-, CN 3-72 Cl 6-, NH.sub.2 3-73 Cl 3-, NH.sub.2 5-, OMe 3-74 CH.sub.2F 4-, OEt 3-75 Cl 4-, OMe 5-, OMe 3-76 Cl 3-, OEt 3-77 Cl 6-, Me 4-, Br 3-78 Cl 5-, Me 3-, Br 3-79 Cl 4-, N.sub.3 3-80 Cl [00179] 3-81 Cl [00180] 3-82 Cl [00181] 3-83 Cl [00182] 3-84 Cl [00183] 3-85 Cl [00184] 3-86 Cl [00185] 3-87 Cl [00186] 3-88 Cl [00187] 3-89 Cl [00188] 3-90 Cl [00189] 3-91 Br [00190] 3-92 Cl [00191] 3-93 Cl [00192] 3-94 Cl [00193] 3-95 Cl [00194] 3-96 OCHF.sub.2 [00195] 3-97 Cl [00196] 3-98 Cl [00197] 3-99 Cl [00198] 3-100 Cl [00199] 3-101 F [00200] 3-102 Cl [00201] 3-103 Cl [00202] 3-104 Cl [00203] 3-105 Cl [00204] 3-106 Cl [00205] 3-107 Cl [00206] 3-108 Cl [00207] 3-109 Br [00208] 3-110 OEt [00209] 3-111 Cl [00210] 3-112 Cl [00211] 3-113 Cl [00212] 3-114 Cl [00213] 3-115 Cl [00214] 3-116 Cl [00215] 3-117 Cl [00216] 3-118 Me [00217] 3-119 Cl [00218] 3-120 Cl [00219] 3-121 Cl [00220] 3-122 CN [00221] 3-123 Cl [00222] 3-124 Cl [00223] 3-125 Cl [00224] 3-126 Cl [00225] 3-127 Cl [00226] 3-128 CF.sub.2CF.sub.3 [00227] 3-129 Cl [00228] 3-130 Cl [00229] 3-131 Cl [00230] 3-132 CF.sub.3 [00231] 3-133 CF.sub.3 [00232] 3-134 CF.sub.3 [00233] 3-135 CF.sub.3 [00234] 3-136 CF.sub.3 3-, OEt 6-, CH.sub.2F 3-137 CF.sub.3 3-, F 4-, Me 5-, F

TABLE-US-00004 TABLE 4 Structure of group M in the derivative Compound I I [00235] No. M M-1 [00236] M-2 [00237] M-3 [00238] M-4 [00239] M-5 [00240] M-6 [00241] M-7 [00242] M-8 [00243] M-9 [00244] M-10 [00245] M-11 [00246] M-12 [00247] M-13 [00248] M-14 [00249] M-15 [00250] M-16 [00251] M-17 [00252] M-18 [00253] M-19 [00254] M-20 [00255] M-21 [00256] M-22 [00257] M-23 [00258] M-24 [00259] M-25 [00260] M-26 [00261] M-27 [00262] M-28 [00263] M-29 [00264] M-30 [00265] M-31 [00266] M-32 [00267] M-33 [00268] M-34 [00269] M-35 [00270] M-36 [00271] M-37 [00272] M-38 [00273] M-39 [00274] M-40 [00275] M-41 [00276] M-42 [00277] M-43 [00278] M-44 [00279] M-45 [00280] M-46 [00281] M-47 [00282] M-48 [00283] M-49 [00284] M-50 [00285] M-51 [00286] M-52 [00287] M-53 [00288] M-54 [00289] M-55 [00290] M-56 [00291] M-57 [00292] M-58 [00293] M-59 [00294] M-60 [00295] M-61 [00296] M-62 [00297] M-63 [00298] M-64 [00299] M-65 [00300] M-66 [00301] M-67 [00302] M-68 [00303] M-69 [00304] M-70 [00305] M-71 [00306] M-72 [00307] M-73 [00308] M-74 [00309] M-75 [00310] M-76 [00311] M-77 [00312] M-78 [00313] M-79 [00314] M-80 [00315] M-81 [00316] M-82 [00317] M-83 [00318] M-84 [00319] M-85 [00320] M-86 [00321] M-87 [00322] M-88 [00323] M-89 [00324] M-90 [00325] M-91 [00326] M-92 [00327] M-93 [00328] M-94 [00329] M-95 [00330] M-96 [00331] M-97 [00332] M-98 [00333] M-99 [00334] M-100 [00335] M-101 [00336] M-102 [00337] M-103 [00338] M-104 [00339] M-105 [00340] M-106 [00341] M-107 [00342] M-108 [00343] M-109 [00344] M-110 [00345] M-111 [00346] M-112 [00347] M-113 [00348] M-114 [00349] M-115 [00350] M-116 [00351] M-117 [00352] M-118 [00353] M-119 [00354] M-120 [00355] M-121 [00356] M-122 [00357] M-123 [00358] M-124 [00359] M-125 [00360] M-126 [00361] M-127 [00362] M-128 [00363] M-129 [00364] M-130 [00365] M-131 [00366] M-132 [00367] M-133 [00368] M-134 [00369] M-135 [00370] M-136 [00371] M-137 [00372] M-138 [00373] M-139 [00374] M-140 [00375] M-141 [00376] M-142 [00377] M-143 [00378] M-144 [00379] M-145 [00380] M-146 [00381] M-147 [00382] M-148 [00383] M-149 [00384] M-150 [00385] M-151 [00386] M-152 [00387] M-153 [00388] M-154 [00389] M-155 [00390] M-156 [00391] M-157 [00392] M-158 [00393] M-159 [00394] M-160 [00395] M-161 [00396] M-162 [00397] M-163 [00398] M-164 [00399] M-165 [00400] M-166 [00401] M-167 [00402] M-168 [00403] M-169 [00404] M-170 [00405] M-171 [00406] M-172 [00407] M-173 [00408] M-174 [00409] M-175 [00410] M-176 [00411] M-177 [00412] M-178 [00413] M-179 [00414] M-180 [00415] M-181 [00416] M-182 [00417] M-183 [00418] M-184 [00419] M-185 [00420] M-186 [00421] M-187 [00422] M-188 [00423] M-189 [00424] M-190 [00425] M-191 [00426] M-192 [00427] M-193 [00428] M-194 [00429] M-195 [00430] M-196 [00431] M-197 Me M-198 Et M-199 [00432] M-200 CN M-201 [00433] M-202 [00434] M-203 [00435] M-204 [00436] M-205 [00437] M-206 [00438] M-207 [00439] M-208 [00440] M-209 [00441] M-210 [00442] M-211 [00443] M-212 [00444] M-213 [00445] M-214 [00446] M-215 [00447] M-216 [00448]

TABLE-US-00005 TABLE 5 Structure and .sup.1HNMR data of the derivative Compound I I [00449] No. X [00450] M .sup.1HNMR I-1 Cl [00451] M-63 .sup.1H NMR (500 MHz, Chloroform-d) 8.85 (d, J = 1.2 Hz, 1H), 8.64 (dd, J = 5.1, 1.3 Hz, 1H), 7.68-7.47 (m, 1H), 7.55 (dd, J = 8.1, 4.9 Hz, 1H), 7.52 (s, 1H), 3.78-3.67 (m, 4H), 3.45- 3.33 (m, 4H) I-2 Cl [00452] M-205 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 8.66 (d, J = 5.3 Hz, 2H), 7.91 (d, J = 5.0 Hz, 2H), 7.39 (s, 1H). 5.63 (q, J = 7.5 Hz, 1H), 4.39 (hept, J = 8.0 Hz, 1H), 1.49 (d, J =7.5 Hz, 3H), 1.42 (d, J = 8.0 Hz, 6H). I-3 Cl [00453] M-123 .sup.1H NMR (500 MHz, Chloroform-d) 9.05 (d, J = 1.1 Hz, 1H), 8.64 (dd, J = 5.1, 1.3 Hz, 1H), 8.08-8.01 (m, 1H), 7.86 (s, 1H), 7.55 (dd, J = 8.0, 5.0 Hz, 1H), 3.04-2.88 (m, 4H), 1.53- 1.33 (m, 4H), 1.43-1.32 (m, 2H) I-4 Cl [00454] M-52 .sup.1H NMR (500 MHz, Chloroform-d) 8.85 (d, J = 1.2 Hz, 1H), 8.64 (dd, J = 5.1, 1.3 Hz, 1H), 7.68-7.47 (m, 1H), 7.55 (dd, J = 8.1, 4.9 Hz, 1H), 7.52 (s, 1H), 7.31 (dd, J = 8.0, 7.5 Hz, 1H), 6.36 (dd, J = 7.5, 1.5 Hz, 1H), 5.54 (dd, J = 8.0, 1.7 Hz, 1H). I-5 Cl [00455] M-165 .sup.1H NMR (500 MHz, Chloroform-d) 8.86 (d, J = 1.2 Hz, 1H), 8.64 (dd, J = 5.1, 1.3 Hz, 1H), 7.99-7.82 (m, 1H), 7.55 (dd, J = 8.0, 5.0 Hz, 1H), 7.42 (s, 1H), 2.56 (s, 3H), 2.43 (s, 3H). I-6 Cl [00456] M-216 .sup.1H NMR (500 MHz, Chloroform-d) 7.55-7.47 (m, 2H), 7.41-7.33 (m, 2H), 7.16 (s, 1H), 2.59 (q, J = 8.0 Hz, 2H), 2.47 (s, 3H), 1.01 (t, J = 8.0 Hz, 3H). I-7 Cl [00457] M-53 (500 MHz, Chloroform-d) 8.88 (d, J = 1.5 Hz, 1H), 8.64 (dd, J = 5.0, 1.5 Hz, 1H), 7.99-7.83 (m, 1H), 7.55 (dd, J = 8.0, 5.0 Hz, 1H), 7.50 (s, 1H), 2.85 (t, J = 7.5 Hz, 2H), 1.94-1.80 (m, 2H), 1.38-1.20 (m, 10H), 0.89 (t, J = 7.5 Hz, 3H). I-8 Cl [00458] M-1 I-9 Cl [00459] M-2 I-10 Cl [00460] M-7 I-11 Cl [00461] M-12 I-12 Cl [00462] M-24 I-13 Cl [00463] M-27 I-14 Cl [00464] M-37 I-15 Cl [00465] M-58 I-16 Cl [00466] M-60 I-17 Cl [00467] M-77 I-18 Cl [00468] M-92 I-19 Cl [00469] M-104 I-20 Cl [00470] M-108 I-21 Cl [00471] M-120 I-22 Cl [00472] M-121 I-23 Cl [00473] M-125 I-24 Cl [00474] M-126 I-25 Cl [00475] M-127 I-26 Cl [00476] M-128 I-27 Cl [00477] M-131 I-28 Cl [00478] M-132 I-29 Cl [00479] M-162 I-30 Cl [00480] M-168 I-31 Cl [00481] M-198 I-32 Cl [00482] M-199 I-33 Br [00483] M-200 I-34 CHF.sub.2 [00484] M-203 I-35 Me [00485] M-204 I-36 OEt [00486] M-207 I-37 OCF.sub.3 [00487] M-208 I-38 CN [00488] M-209 I-39 F [00489] M-211

[0095] 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.

[0096] 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.

[0097] Examples of representative compounds are as follows:

[0098] 1. Synthesis of Compound 1-7

##STR00490##

[0099] (1) To a three-necked round bottom flask, compound 1-7-a (10 g, 67 mmol), compound 1-7-b (10.5 g, 67 mmol) and potassium carbonate (27.8 g, 201 mmol) were charged, and nitrogen replacement was performed three times after the addition of 1,4-dioxane (100 mL)/water (20 mL). Pd(dppf)Cl.sub.2CH.sub.2Cl.sub.2 (0.2 g) was added quickly under nitrogen protection and then nitrogen replacement was performed three times. The reaction solution was treated by nitrogen replacement for another three times and reacted at 100 C. for 16 h. After high performance liquid chromatography detection showed the completion of the reaction, the reaction system was concentrated and subjected to column chromatography separation to obtain 12 g (53 mmol, yield 80%) of compound 1-7-c (white solid).

[0100] (2) To a three-necked round bottom flask, compound 1-7-c (12 g, 53 mmol), N-chloro succimide (7.1 g, 53 mmol), benzoyl peroxide (0.5 g, catalytic amount) and acetonitrile (120 mL) were charged and reacted at 80 C. for 16 h. A small amount of the raw material was detected to remain by high performance liquid chromatography. The reaction system was concentrated and subjected to column chromatography separation to obtain 6 g (23 mmol, yield 43%) of compound 1-7-d (white solid).

[0101] (3) To a three-necked round bottom flask, compound 1-7-d (1 g, 3.8 mmol), potassium acetate (1.88 g, 19 mmol) and 10 mL of DMSO were charged and reacted at 120 C. for 2 h. After high performance liquid chromatography detection showed the completion of the reaction, the reaction solution was cooled to 25 C. and charged with 1M HCl in a dropwise manner with temperature control (no higher than 25 C.) till pH of the solution was around 5. Solid was precipitated out, which was collected by suction filtration, washed with a large quantity of water, purified by beating with methyl tert-butyl ether (20 mL) and a small amount of methanol (1 mL). After suction filtration, the solid was dried to obtain 500 mg (2 mmol, yield 54%) of compound 1-7 (off-white solid).

[0102] 2. Synthesis of Compound I-1

##STR00491##

[0103] With reference to the above method 1, compound 1-1 was prepared. To a round bottom flask, compound 1-1 (1 g, 4.8 mmol), potassium carbonate (2 g, 14.4 mmol) and acetonitrile (20 mL) were charged, the reaction system was further charged with compound I-1-a (1.08 g, 7.2 mmol) in a dropwise manner at 25 C. and reacted at 25 C. for 5 h. High performance liquid chromatography detection showed the completion of the reaction. The reaction system was filtered to remove remaining potassium carbonate solid, the mother liquid was concentrated and separated through column chromatography to obtain 1 g (3.1 mmol, yield 67%) of compound I-1 (white solid).

[0104] 3. Synthesis of Compound I-2

##STR00492##

[0105] With reference to the above method 1, compound 2-1 was prepared. To a round bottom flask, compound 2-1 (2 g, 9.6 mmol), potassium carbonate (4 g, 28.8 mmol), compound I-2-a (2.4 g, 14.4 mmol) and acetonitrile (40 mL) were charged and reacted at 25 C. overnight. High performance liquid chromatography detection showed the completion of the reaction. The reaction system was filtered to remove remaining potassium carbonate solid, the mother liquid was concentrated and separated by prep-HPLC to obtain compound I-2 as a yellow solid (600 mg, yield 18.5%).

[0106] 4. Synthesis of Compound I-3

##STR00493##

[0107] With reference to the above method 1, compound 1-1 was prepared. To a 50 mL single-necked eggplant-shaped flask, compound 1-1 (1 equiv.),

##STR00494##

(1.1equiv.), potassium carbonate (3 equiv.) and acetonitrile (10V) were charged, then heated to 80 C. and stirred for 6 h. TLC detection showed the completion of the reaction. The reaction system was subjected to vacuum distillation to remove acetonitrile, then charged with water for dissolution and extracted with ethyl acetate (5V*3), which was then removed by vacuum distillation. The residue was separated through silica gel column chromatography (100 mesh to 200 mesh) to obtain the product with yield of 82%.

[0108] 5. Synthesis of Compound I-4

##STR00495##

[0109] With reference to the above method 1, compound 1-1 was prepared. To a 50 mL single-necked eggplant-shaped flask, compound 1-1 (1 equiv.), triethyl amine (3 equiv.) and dichloromethane (5V), then charged with

##STR00496##

(1.2 equiv.) in a dropwise manner in ice bath, and stirred at room temperature for 30 min. TLC detection showed the completion of the reaction. The reaction system was added with water (5V) and extracted with dichloromethane (5V*3), which was then removed by vacuum distillation. The residue was separated through silica gel column chromatography (100 mesh to 200 mesh) to obtain the product with yield of 76%.

[0110] 6. Synthesis of Compound I-5

##STR00497##

[0111] With reference to the above method 1, compound 1-1 was prepared. To a 50 mL eggplant-shaped flask, compound 1-1 (1 equiv.), Phenofluor (1.5 equiv.), cesium fluoride (3 equiv.) and toluene (10 V) were charged, then heated to 80 C. and stirred for 18 h. TLC detection showed the completion of the reaction. Intermediate 1-5-a was obtained after work-up. To another 50 mL single-necked eggplant-shaped flask, compound 1-5-a (1 equiv.),

##STR00498##

(1.2 equiv.), potassium carbonate (3 equiv.) and acetonitrile (10 V) were charged, then heated to 80 C. and stirred for 18 h. TLC detection showed the completion of the reaction. The reaction system was subjected to vacuum distillation to remove acetonitrile, then added with water (5V) for dissolution and extracted with ethyl acetate (5V*3), which was then removed by vacuum distillation. The residue was separated through silica gel column chromatography (100 mesh to 200 mesh) to obtain the product with yield of 62%.

[0112] 7. Synthesis of Compound I-6

##STR00499##

[0113] With reference to the above method 1, compound 1-1 was prepared. To a 50 mL single-necked eggplant-shaped flask, compound 1-1 (1 equiv.), POCl.sub.3 (1.5 equiv.), 1,2-dichloroethane (10 V) and 5% N,N-dimethylformamide were charged, then heated to 80 C. and stirred for 6 h. TLC detection showed the completion of the reaction, then the reaction was charged with water (5V) for dissolution and extracted with 1,2-dichloroethane (5V*3), which was removed by vacuum distillation to obtain compound I-6-a. To another 50 mL single-necked eggplant-shaped flask, compound 1-6-a (1 equiv.),

##STR00500##

(1.2 equiv.), potassium hydrate (3 equiv.) and N,N-dimethyl formamide (10 V) were charged, then heated to 100 C. and stirred for 18 h. TLC detection showed the completion of the reaction, then the reaction was charged with water (5V) for dissolution and extracted with ethyl acetate (5V*3), which was then removed by vacuum distillation. The residue was separated through silica gel column chromatography (100 mesh to 200 mesh) to obtain the product with yield of 49%.

[0114] Evaluation of Biological Activity:

[0115] The activity level standard of harmful plant destruction (i.e. growth inhibition rate) is as follows:

[0116] Level 10: completely dead;

[0117] Level 9: above 90% growth inhibition rate;

[0118] Level 8: above 80% growth inhibition rate;

[0119] Level 7: above 70% growth inhibition rate;

[0120] Level 6: above 60% growth inhibition rate;

[0121] Level 5: above 50% growth inhibition rate;

[0122] Level 4: above 40% growth inhibition rate;

[0123] Level 3: above 30% growth inhibition rate;

[0124] Level 2: above 20% growth inhibition rate;

[0125] Level 1: below 20% growth inhibition rate;

[0126] Level 0: no effect.

[0127] The above described growth inhibition rates are fresh weight inhibition rates.

[0128] Experiment of post-emergence test: monocotyledonous and dicotyledonous weed seeds as well as main crop seeds (i.e., wheat, corn, rice, soybean, cotton, oilseed rape, millet and sorghum) were put into aplastic pot loaded with soil, then covered with 0.5-2 cm of soil, and the seeds were allowed to grow in good greenhouse environment. The test plants were treated at 4-5 leaf stage 2-3 week safter sowing. The test compounds of the invention were dissolved in acetone respectively, then added with Tween-80 and diluted by a certain amount of water to give solutions with certain concentrations. The solution was sprayed to the plants with as prayer. The plants were cultured for 3 weeks in the greenhouse. The experiment results of weed controlling effect after 3 weeks were listed in Table 6.

TABLE-US-00006 TABLE 6 Experiment on weed control effect of compounds of Formula I and their derivatives of Formula I' in Post-emergence stage Com- pound Amaranthus Rorippa Veronica No. retroflexus indica polita Chenopodiaceae Dose 1-1 10 10 10 10 2000 g/ha 1-2 10 10 10 10 2000 g/ha 1-3 10 10 10 10 2000 g/ha 1-4 10 10 10 10 2000 g/ha 1-5 10 10 10 10 2000 g/ha 1-6 10 10 7 10 2000 g/ha 1-7 10 10 10 10 2000 g/ha 1-8 10 10 10 10 2000 g/ha 1-11 10 10 10 10 2000 g/ha 1-23 10 10 10 10 2000 g/ha 1-57 10 10 10 10 2000 g/ha 1-58 10 10 10 10 2000 g/ha 1-60 10 10 7 10 2000 g/ha 1-63 10 10 10 10 2000 g/ha 1-90 10 10 7 10 2000 g/ha 1-105 10 10 10 10 2000 g/ha 1-131 10 10 10 10 3000 g/ha 2-3 10 10 10 10 1000 g/ha 2-5 10 10 10 10 1000 g/ha 2-10 10 10 10 10 1000 g/ha 2-11 10 10 10 10 1000 g/ha 2-13 10 10 10 10 1000 g/ha 2-23 10 10 10 10 1000 g/ha 3-3 10 10 10 10 2000 g/ha 3-7 10 10 10 10 2000 g/ha 3-8 10 10 10 10 2000 g/ha 3-18 10 10 10 10 2000 g/ha 3-19 10 10 10 10 2000 g/ha 3-30 10 10 10 10 2000 g/ha I-1 10 10 10 10 2000 g/ha I-4 10 10 10 10 2000 g/ha I-7 10 10 10 10 2000 g/ha

Comparative Experiment

[0129] The post-emergence test conditions were the same as above, and the results are shown in Table 7.

##STR00501##

TABLE-US-00007 TABLE 7 Results of comparison experiment Echinochloa Setaria Digitaria Rorippa Galium Veronica Compound crus-galli viridis sanguinalis indica aparine polita Dose 1-1 8 10 7 10 9 9 300 g/ha 1-2 10 10 8 10 9 10 300 g/ha 1-4 8 10 8 10 10 10 300 g/ha 1-7 10 10 8 10 9 10 300 g/ha 2-3 10 10 10 10 10 10 300 g/ha 1-7 8 9 7 10 9 9 300 g/ha Control 0 2 1 3 5 6 300 g/ha Compound A Control 0 2 0 3 4 6 300 g/ha Compound B

[0130] It can be seen from the above table, the compounds of the present invention obviously have higher herbicidal activity compared with the control compounds A and B.

Experiment of Pre-Emergence Test

[0131] 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 of 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 3 weeks later. It was observed that the herbicides of the present invention mostly had excellent effect at dose of 250 g/ha, especially to weeds such as Echinochloa crusgalli, Digitaria sanguinalis and Abutilon theophrasti, etc., and many compounds had good selectivity for corn, wheat, rice, soybean, oilseed rape, etc.

[0132] Transplanted rice safety evaluation and weed control effect evaluation in rice field:

[0133] Rice field soil was loaded into a 1/1,000,000 ha pot. The seeds of Echinochloa crusgalli, Scirpus juncoides, Bidens tripartite and Sagittaria trifolia L. were sowed and gently covered with soil, then left to stand still in greenhouse in the state of 0.5-1 cm of water storage. The tuber of Sagittaria trifolia L. was planted in the next day or 2 days later. It was kept at 3-4 cm of water storage thereafter. The weeds were treated by dripping the WP or SC water diluents prepared according to the common preparation method of the compounds of the present invention with pipette homogeneously to achieve specified effective amount when Echinochloa crusgalli, Scirpus juncoides and Bidens tripartite reached 0.5 leaf stage and Sagittaria trifolia L. reached the time point of primary leaf stage.

[0134] In addition, the rice field soil that loaded into the 1/1,000,000 ha pot was leveled to keep water storage at 3-4 cm depth. The 3 leaf stage rice (japonica rice) was transplanted at 3 cm of transplanting depth the next day. The compound of the present invention was treated by the same way after 5 days of transplantation.

[0135] The fertility condition of Echinochloa crusgalli, Scirpus juncoides, Bidens tripartite and Sagittaria trifolia L. 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 1-10 activity standard level. It has been found that many of the compounds of the present invention have excellent activity and selectivity, especially for Sagittaria trifolia L. and Echinochloa crusgalli.

[0136] Note: The seeds of Echinochloa crusgalli, Scirpus juncoides, Sagittaria trifolia L. and Bidens tripartite were collected from Heilongjiang Province of China. Tests indicated that the weeds were resistant to common rate of pyrazosulfuron-ethyl.

[0137] At the same time, it is found after several tests that the compound and the composition 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 broadleaf 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.