R-TYPE PYRIDYLOXYCARBOXYLIC ACID, SALT AND ESTER DERIVATIVE THEREOF, AND PREPARATION METHOD THEREFOR, AND HERBICIDAL COMPOSITION AND APPLICATION THEREOF

Abstract

The invention relates to the field of pesticide technology, and in particular to a type of R-pyridyloxycarboxylic acid and salt, ester derivative, preparation method, herbicidal composition and application thereof. The R-pyridyloxycarboxylic acid is represented by formula I,

##STR00001##

wherein, A, B each independently represent halogen, alkyl or cycloalkyl with or without halogen; C represents hydrogen, halogen, alkyl, haloalkyl; Q represents halogen, cyano, cyanoalkyl and the like; Y represents nitro or NR.sub.1R.sub.2; the salt is metal salt, amine salt, sulfonium salt, phosphonium salt; the ester is

##STR00002##

wherein, X represents O or S; M represents alkyl, alkenyl, alkynyl and the like with or without halogen. The compound has excellent herbicidal activity and higher crop safety, especially good selectivity for key crops such as rice.

Claims

1. An R-pyridyloxycarboxylic acid represented by formula I and salt, ester derivative thereof, ##STR00484## wherein: A and B each independently represent halogen; or alkyl or cycloalkyl optionally substituted with halogen; C represents hydrogen, halogen, alkyl or haloalkyl; Q represents halogen, cyano, cyanoalkyl, hydroxyalkyl, amino, nitro, formyl; alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylaminoalkyl or alkoxyalkyl optionally substituted with halogen; or unsubstituted or substituted aryl, heteroaryl, arylalkyl, heteroarylalkyl; Y represents nitro or NR.sub.1R.sub.2, wherein R.sub.1 represents H; alkyl, alkenyl or alkynyl optionally substituted by 1-2 R.sub.11; —COR.sub.12, nitro, OR.sub.13, SO.sub.2R.sub.14, NR.sub.15R.sub.16, N═CR.sub.17R.sub.18, alkylcarbamoyl, dialkylcarbamoyl, trialkylsilyl or dialkylphosphono; R.sub.2 represents H; alkyl optionally substituted by 1-2 R.sub.11; or —COR.sub.12; or NR.sub.1R.sub.2 represents N═CR.sub.21NR.sub.22R.sub.23, N═CR.sub.24OR.sub.25; or a 5- or 6-membered saturated or unsaturated ring with or without oxygen atom, sulfur atom, or additional nitrogen atom, which is unsubstituted or substituted by 1-2 groups independently selected from the group consisting of halogen, alkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, dialkylamino, and alkoxycarbonyl; wherein R.sub.11 independently represents halogen, hydroxy, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, dialkylamino, alkoxycarbonyl; or unsubstituted or substituted aryl, heteroaryl; R.sub.12 represents H, alkyl, haloalkyl, alkoxy, phenyl, phenoxy or benzyloxy; R.sub.13 represents H, alkyl, haloalkyl, phenyl, benzyl or CHR.sub.31C(O)OR.sub.32; R.sub.31 represents H, alkyl or alkoxy; R.sub.32 represents H, alkyl or benzyl; R.sub.14 represents alkyl or haloalkyl; R.sub.15 represents H, alkyl, formyl, alkylacyl, haloalkylacyl, alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl or benzyloxycarbonyl; R.sub.16 represents H or alkyl; R.sub.17 represents H, alkyl; or phenyl that is unsubstituted or substituted by 1-3 groups selected from the group consisting of halogen, alkyl, and alkoxy; R.sub.18 represents H or alkyl; or N═CR.sub.17R.sub.18 represents ##STR00485## R.sub.21 and R.sub.24 each independently represent H or alkyl; R.sub.22 and R.sub.23 each independently represent H or alkyl; or NR.sub.22R.sub.23 represents a 5- or 6-membered saturated or unsaturated ring with or without oxygen atom, sulfur atom, or additional nitrogen atom; R.sub.25 represents alkyl; the salt is metal salt, amine salt, sulfonium salt or phosphonium salt; the ester is represented by formula I-1 ##STR00486## wherein: X represents O or S; M represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, -alkyl-Z, ##STR00487## optionally substituted with halogen; or unsubstituted or substituted heterocyclyl, aryl, heteroaryl; Z represents ##STR00488## cyano, nitro, or unsubstituted or substituted heterocyclyl, aryl, heteroaryl; R.sub.3 each independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl or unsubstituted or substituted heterocyclyl, aryl, heteroaryl, heterocyclylalkyl, arylalkyl, heteroarylalkyl; R.sub.4, R.sub.5, and R.sub.6 each independently represent hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxycarbonyl or unsubstituted or substituted heterocyclyl, aryl, heteroaryl, heterocyclylalkyl, arylalkyl, heteroarylalkyl.

2. The R-pyridyloxycarboxylic acid and salt, ester derivative thereof according to claim 1, wherein A and B each independently represent halogen; or C1-C8 alkyl or C3-C8 cycloalkyl optionally substituted with halogen; C represents hydrogen, halogen, C1-C8 alkyl or halo C1-C8 alkyl; Q represents halogen, cyano, cyano C1-C8 alkyl, hydroxy C1-C8 alkyl, amino, nitro, formyl; C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, C1-C8 alkylamino C1-C8 alkyl or C1-C8 alkoxy C1-C8 alkyl optionally substituted with halogen; or unsubstituted or substituted aryl, heteroaryl, aryl C1-C8 alkyl, heteroaryl C1-C8 alkyl; Y represents nitro or NR.sub.1R.sub.2, wherein R.sub.1 represents H; C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl optionally substituted by 1-2 R.sub.11; —COR.sub.12, nitro, OR.sub.13, SO.sub.2R.sub.14, NR.sub.15R.sub.16, N═CR.sub.17R.sub.18, C1-C8 alkylcarbamoyl, di-C1-C8 alkylcarbamoyl, tri-C1-C8 alkylsilyl or di-C1-C8 alkylphosphono; R.sub.2 represents H; C1-C8 alkyl optionally substituted by 1-2 R.sub.11; or —COR.sub.12; or NR.sub.1R.sub.2 represents N═CR.sub.21NR.sub.22R.sub.23, N═CR.sub.24OR.sub.25; or ##STR00489## that is unsubstituted or substituted by 1-2 groups independently selected from the group consisting of halogen, C1-C8 alkyl, C1-C8 alkoxy, halo C1-C8 alkoxy, C1-C8 alkylthio, halo C1-C8 alkylthio, amino, C1-C8 alkylamino, di-C1-C8 alkylamino, and C1-C8 alkoxycarbonyl; wherein R.sub.11 independently represents halogen, hydroxy, C1-C8 alkoxy, halo C1-C8 alkoxy, C1-C8 alkylthio, halo C1-C8 alkylthio, amino, C1-C8 alkylamino, di-C1-C8 alkylamino, C1-C8 alkoxycarbonyl; or phenyl, naphthyl ##STR00490## that is unsubstituted or substituted by 1-3 groups selected from the group consisting of halogen, C1-C8 alkyl, halo C1-C8 alkyl, C1-C8 alkoxy, and nitro; R.sub.12 represents H, C1-C18 alkyl, halo C1-C8 alkyl, C1-C8 alkoxy, phenyl, phenoxy or benzyloxy; R.sub.13 represents H, C1-C8 alkyl, halo C1-C8 alkyl, phenyl, benzyl or CHR.sub.31C(O)OR.sub.32; R.sub.31 represents H, C1-C8 alkyl or C1-C8 alkoxy; R.sub.32 represents H, C1-C8 alkyl or benzyl; R.sub.14 represents C1-C8 alkyl or halo C1-C8 alkyl; R.sub.15 represents H, C1-C8 alkyl, formyl, C1-C8 alkylacyl, halo C1-C8 alkylacyl, C1-C8 alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl or benzyloxycarbonyl; R.sub.16 represents H or C1-C8 alkyl; R.sub.17 represents H, C1-C8 alkyl; or phenyl that is unsubstituted or substituted by 1-3 groups selected from the group consisting of halogen, C1-C8 alkyl, C1-C8 alkoxy; R.sub.18 represents H or C1-C8 alkyl; or N═CR.sub.17R.sub.18 represents ##STR00491## R.sub.21 and R.sub.24 each independently represent H or C1-C8 alkyl; R.sub.22 and R.sub.23 each independently represent H or C1-C8 alkyl; or NR.sub.22R.sub.23 represents ##STR00492## R.sub.25 represents C1-C8 alkyl; the salt is metal salt, ammonium salt NH.sub.4.sup.+, primary amine RNH.sub.2 salt, secondary amine (R).sub.2NH salt, tertiary amine (R).sub.3N salt, quaternary amine salt (R).sub.4N.sup.+, morpholine salt, piperidine salt, pyridine salt, aminopropyl morpholine salt, Jeff amine D-230 salt, the salt of 2,4,6-tri(dimethylaminomethyl) phenol and sodium hydroxide, alkylsulfonium salt, alkylsulfoxonium salt, alkylphosphonium salt or alkanolphosphonium salt; wherein: R each independently represents unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl or phenyl, and the foregoing groups are optionally substituted by one or more of the following groups: halogen, hydroxy, alkoxy, alkylthio, hydroxyalkoxy, amino, alkylamino, aminoalkylamino, and phenyl; in formula I-1, X represents O or S; M represents C1-C18 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, —(C1-C8 alkyl)-Z, ##STR00493## optionally substituted with halogen, or unsubstituted or substituted heterocyclyl, aryl, heteroaryl; Z represents ##STR00494## cyano, nitro, or unsubstituted or substituted heterocyclyl, aryl, heteroaryl; R.sub.3 each independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl or unsubstituted or substituted heterocyclyl, aryl, heteroaryl, heterocyclyl C1-C8 alkyl, aryl C1-C8 alkyl, heteroaryl C1-C8 alkyl; R.sub.4, R.sub.5, and R.sub.6 each independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C1-C8 alkoxycarbonyl or unsubstituted or substituted heterocyclyl C1-C8 alkyl, aryl C1-C8 alkyl, heteroaryl C1-C8 alkyl; wherein the heterocyclyl is selected from the group consisting of ##STR00495## with 0, 1 or 2 oxo groups; the aryl is phenyl or naphthyl; the heteroaryl is selected from the group consisting of ##STR00496## ##STR00497## which is optionally substituted by at least one group selected from the group consisting of halogen, nitro, cyano, thiocyano, hydroxy, carboxy, mercapto, formyl; phenyl, benzyl, benzyloxy, and phenoxy that is unsubstituted or substituted by at least one group from the group consisting of halogen, alkyl, alkoxy; alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, OR″, SR″, -alkyl-OR″, -alkyl-SR″, COR″, COOR″, COSR″, SOR″, SO.sub.2R″, OCOR″, SCOR″ optionally substituted with halogen; and amino or aminocarbonyl substituted by one or two groups selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, phenyl, benzyl, benzyloxy, phenoxy, COR″, COOR″, SO.sub.2R″, and OR″; R′ each independently represents hydrogen, nitro, hydroxy, amino; or alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkoxyalkyl, alkoxycarbonyl, alkylthiocarbonyl, alkylsulfonyl, alkylsulfonylalkyl, alkylcarbonyl, alkylcarbonylalkyl, alkylacyloxy, alkylamino, alkylaminocarbonyl, alkoxyaminocarbonyl, alkoxycarbonylalkyl, alkylaminocarbonylalkyl, trialkylsilyl, dialkylphosphono optionally substituted with halogen; R″ each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl.

3. The R-pyridyloxycarboxylic acid and salt, ester derivative thereof according to claim 2, wherein A and B each independently represent halogen; or C1-C6 alkyl or C3-C6 cycloalkyl optionally substituted with halogen; C represents hydrogen, halogen, C1-C6 alkyl or halo C1-C6 alkyl; Q represents halogen, cyano, cyano C1-C6 alkyl, hydroxy C1-C6 alkyl, amino, nitro, formyl; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylamino C1-C6 alkyl or C1-C6 alkoxy C1-C6 alkyl optionally substituted with halogen; or unsubstituted or substituted aryl, heteroaryl, aryl C1-C6 alkyl, heteroaryl C1-C6 alkyl; Y represents nitro or NR.sub.1R.sub.2, wherein R.sub.1 represents H; C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl optionally substituted by 1-2 R.sub.11; —COR.sub.12, nitro, OR.sub.13, SO.sub.2R.sub.14, NR.sub.15R.sub.16, N═CR.sub.17R.sub.18, C1-C6 alkylcarbamoyl, di-C1-C6 alkylcarbamoyl, tri-C1-C6 alkylsilyl or di-C1-C6 alkylphosphono; R.sub.2 represents H; C1-C6 alkyl optionally substituted by 1-2 R.sub.11; or —COR.sub.12; or NR.sub.1R.sub.2 represents N═CR.sub.21NR.sub.22R.sub.23, N═CR.sub.24OR.sub.25; or ##STR00498## that is unsubstituted or substituted by 1-2 groups independently selected from the group consisting of halogen, C1-C6 alkyl, C1-C6 alkoxy, halo C1-C6 alkoxy, C1-C6 alkylthio, halo C1-C6 alkylthio, amino, C1-C6 alkylamino, di-C1-C6 alkylamino, and C1-C6 alkoxycarbonyl; wherein R.sub.11 independently represents halogen, hydroxy, C1-C6 alkoxy, halo C1-C6 alkoxy, C1-C6 alkylthio, halo C1-C6 alkylthio, amino, C1-C6 alkylamino, di-C1-C6 alkylamino, C1-C6 alkoxycarbonyl; or phenyl, naphthyl ##STR00499## that is unsubstituted or substituted by 1-3 groups selected from the group consisting of halogen, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxy, and nitro; R.sub.12 represents H, C1-C14 alkyl, halo C1-C6 alkyl, C1-C6 alkoxy, phenyl, phenoxy or benzyloxy; R.sub.13 represents H, C1-C6 alkyl, halo C1-C6 alkyl, phenyl, benzyl or CHR.sub.31C(O)OR.sub.32; R.sub.31 represents H, C1-C6 alkyl or C1-C6 alkoxy; R.sub.32 represents H, C1-C6 alkyl or benzyl; R.sub.14 represents C1-C6 alkyl or halo C1-C6 alkyl; R.sub.15 represents H, C1-C6 alkyl, formyl, C1-C6 alkylacyl, halo C1-C6 alkylacyl, C1-C6 alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl or benzyloxycarbonyl; R.sub.16 represents H or C1-C6 alkyl; R.sub.17 represents H, C1-C6 alkyl; or phenyl that is unsubstituted or substituted by 1-3 groups selected from the group consisting of halogen, C1-C6 alkyl, and C1-C6 alkoxy; R.sub.18 represents H or C1-C6 alkyl; or N═CR.sub.17R.sub.18 represents ##STR00500## R.sub.21 and R.sub.24 each independently represent H or C1-C6 alkyl; R.sub.22 and R.sub.23 each independently represent H or C1-C6 alkyl; or NR.sub.22R.sub.23 represents ##STR00501## R.sub.25 represents C1-C6 alkyl; the salt is metal salt, ammonium salt NH.sub.4.sup.+, primary amine RNH.sub.2 salt, secondary amine (R).sub.2NH salt, tertiary amine (R).sub.3N salt, quaternary amine salt (R).sub.4N.sup.+, morpholine salt, piperidine salt, pyridine salt, aminopropyl morpholine salt, Jeff amine D-230 salt, the salt of 2,4,6-tri(dimethylaminomethyl) phenol and sodium hydroxide, C1-C18 alkylsulfonium salt, C1-C18 alkylsulfoxonium salt, C1-C18 alkylphosphonium salt or C1-C18 alkanolphosphonium salt; wherein: R each independently represents unsubstituted C1-C18 alkyl, C2-C18 alkenyl, C2-C18 alkynyl, C3-C18 cycloalkyl or phenyl, and the foregoing groups are optionally substituted by one or more of the following groups: halogen, hydroxy, C1-C8 alkoxy, C1-C8 alkylthio, hydroxy C1-C8 alkoxy, amino, C1-C8 alkylamino, amino C1-C8 alkylamino, and phenyl; in formula I-1, X represents O or S; M represents C1-C18 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, —(C1-C6 alkyl)-Z, ##STR00502## optionally substituted with halogen, or unsubstituted or substituted heterocyclyl, aryl, heteroaryl; Z represents ##STR00503## cyano, nitro, or unsubstituted or substituted heterocyclyl, aryl, heteroaryl; R.sub.3 each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl or unsubstituted or substituted heterocyclyl, aryl, heteroaryl, heterocyclyl C1-C6 alkyl, aryl C1-C6 alkyl, heteroaryl C1-C6 alkyl; R.sub.4, R.sub.5, and R.sub.6 each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkoxycarbonyl or unsubstituted or substituted heterocyclyl C1-C6 alkyl, aryl C1-C6 alkyl, heteroaryl C1-C6 alkyl; wherein the heterocyclyl is selected from the group consisting of ##STR00504## with 0, 1 or 2 oxo groups; the aryl is phenyl or naphthyl; the heteroaryl is selected from the group consisting of ##STR00505## ##STR00506## which is substituted by 0, 1, 2 or 3 groups selected from the group consisting of halogen, nitro, cyano, thiocyano, hydroxy, carboxy, mercapto, formyl; phenyl, benzyl, benzyloxy, phenoxy that is unsubstituted or substituted by at least one group from the group consisting of halogen, C1-C6 alkyl, C1-C6 alkoxy; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, OR″, SR″, —(C1-C6)alkyl-OR″, —(C1-C6)alkyl-SR″, COR″, COOR″, COSR″, SOR″, SO.sub.2R″, OCOR″, SCOR″ optionally substituted with halogen; and amino or aminocarbonyl substituted by one or two groups selected from the group consisting of hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, phenyl, benzyl, benzyloxy, phenoxy, COR″, COOR″, SO.sub.2R″, and OR″; R′ each independently represents hydrogen, nitro, hydroxy, amino; or C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C3-C6 cycloalkyloxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthiocarbonyl, C1-C6 alkylsulfonyl, C1-C6 alkylsulfonyl C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkylcarbonyl C1-C6 alkyl, C1-C6 alkylacyloxy, C1-C6 alkylamino, C1-C6 alkylaminocarbonyl, C1-C6 alkoxyaminocarbonyl, C1-C6 alkoxycarbonyl C1-C6 alkyl, C1-C6 alkylaminocarbonyl C1-C6 alkyl, tri-C1-C6 alkylsilyl, di-C1-C6 alkylphosphono optionally substituted with fluoro, chloro or bromo; R″ each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl or C3-C6 cycloalkyl C1-C6 alkyl.

4. The R-pyridyloxycarboxylic acid and salt, ester derivative thereof according to claim 3, wherein A and B each independently represent halogen, C1-C6 alkyl, halo C1-C6 alkyl or C3-C6 cycloalkyl; C represents hydrogen, halogen, C1-C6 alkyl or halo C1-C6 alkyl; Q represents C1-C6 alkyl, halo C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, halogen, cyano, amino, nitro, formyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkoxycarbonyl, hydroxy C1-C6 alkyl, C1-C6 alkoxy C1-C2 alkyl, cyano C1-C2 alkyl, C1-C6 alkylamino C1-C2 alkyl, benzyl, naphthyl, furyl, thienyl, thiazolyl, pyridyl, pyrimidinyl; ##STR00507## that is unsubstituted or substituted by C1-C6 alkyl; or phenyl that is unsubstituted or substituted by at least one group selected from the group consisting of C1-C6 alkyl, halo C1-C6 alkyl, halogen and C1-C6 alkoxy; Y represents amino, C1-C6 alkylamino, C1-C6 alkylcarbonylamino, phenylcarbonylamino, benzylamino; or furylmethyleneamino that is unsubstituted or substituted by halo C1-C6 alkyl; the salt is metal salt, ammonium salt NH.sub.4.sup.+, primary amine RNH.sub.2 salt, secondary amine (R).sub.2NH salt, tertiary amine (R).sub.3N salt, quaternary amine salt (R).sub.4N.sup.+, morpholine salt, piperidine salt, pyridine salt, aminopropyl morpholine salt, Jeff amine D-230 salt, the salt of 2,4,6-tri(dimethylaminomethyl) phenol and sodium hydroxide, C1-C14 alkylsulfonium salt, C1-C14 alkylsulfoxonium salt, C1-C14 alkylphosphonium salt or C1-C14 alkanolphosphonium salt; wherein: R each independently represents unsubstituted C1-C14 alkyl, C2-C12 alkenyl, C2-C12 alkynyl, C3-C12 cycloalkyl or phenyl; or C1-C14 alkyl optionally substituted by one or more of the following groups: halogen, hydroxy, C1-C6 alkoxy, C1-C6 alkylthio, hydroxy C1-C6 alkoxy, amino, C1-C6 alkylamino, amino C1-C6 alkylamino, and phenyl; in formula I-1, X represents O or S; M represents C1-C18 alkyl, halo C1-C8 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, halo C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylsulfonyl, cyano C1-C2 alkyl, nitro C1-C2 alkyl, C1-C6 alkoxy C1-C2 alkyl, C1-C6 alkoxycarbonyl C1-C2 alkyl, C2-C6 alkenyloxycarbonyl C1-C2 alkyl, —(C1-C2 alkyl)-Z, ##STR00508## tetrahydrofuryl, pyridyl, naphthyl, furyl, thienyl, ##STR00509## that is unsubstituted or substituted by C1-C6 alkyl; or phenyl that is unsubstituted or substituted by C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkylamino, halogen or C1-C6 alkoxy; Z represents ##STR00510## tetrahydrofuryl, pyridyl, ##STR00511## thienyl, furyl, naphthyl; or phenyl that is unsubstituted or substituted by at least one group selected from the group consisting of C1-C6 alkyl, C1-C6 alkoxy, halo C1-C6 alkyl, cyano and halogen; R.sub.3 each independently represents C1-C6 alkyl; R.sub.4, R.sub.5, and R.sub.6 each independently represent hydrogen, C1-C6 alkyl or C1-C6 alkoxycarbonyl; R′ represents hydrogen, C1-C6 alkyl or halo C1-C6 alkyl.

5. The R-pyridyloxycarboxylic acid and salt, ester derivative thereof according to claim 4, wherein A and B each independently represent fluoro, chloro, bromo, iodo, methyl, ethyl, propyl, isopropyl, trifluoromethyl or cyclopropyl; C represents hydrogen, fluoro, chloro, bromo, iodo, methyl or trifluoromethyl; Q represents methyl, ethyl, propyl, isopropyl, cyclopropyl, vinyl, ethynyl, fluoro, chloro, bromo, cyano, amino, nitro, formyl, methoxy, methylthio, methoxycarbonyl, monochloromethyl, monofluoromethyl, difluoromethyl, trifluoromethyl, 2-chloroethyl, 2,2,2-trifluoroethyl, hydroxymethyl, ##STR00512## benzyl, naphthyl, furyl, thiazolyl, pyridyl, pyrimidinyl; thiazolyl that is unsubstituted or substituted by chloro; thienyl that is unsubstituted or substituted by fluoro; ##STR00513## that is unsubstituted or substituted by methyl or fluoro; or phenyl that is unsubstituted or substituted by at least one group selected from the group consisting of methyl, trifluoromethyl, chloro and methoxy; Y represents NH.sub.2, ##STR00514## the salt is metal salt, ammonium salt NH.sub.4.sup.+, primary amine RNH.sub.2 salt, secondary amine (R).sub.2NH salt, tertiary amine (R).sub.3N salt, quaternary amine salt (R).sub.4N.sup.+, morpholine salt, piperidine salt, pyridine salt, aminopropyl morpholine salt, Jeff amine D-230 salt, the salt of 2,4,6-tri(dimethylaminomethyl) phenol and sodium hydroxide, C1-C6 alkylsulfonium salt, C1-C6 alkylsulfoxonium salt, C1-C6 alkylphosphonium salt or C1-C6 alkanolphosphonium salt; wherein: R each independently represents unsubstituted C.sub.1-C14 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C12 cycloalkyl, phenyl or benzyl; or C1-C14 alkyl optionally substituted by one or more of the following groups selected from the group consisting of: hydroxy, C1-C4 alkoxy, C1-C4 alkylthio, hydroxy C1-C4 alkoxy, amino, C1-C4 alkylamino, and amino C1-C4 alkylamino; in formula I-1, X represents O or S; M represents methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, octadecyl, trifluoromethyl, pentafluoroethyl, 3-chlorobutyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 4,4,4-trifluorobutyl, 2,2,3,3,3-pentafluoropropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, allyl, 2-propynyl, methoxy, ethoxycarbonyl, methylsulfonyl, ##STR00515## tetrahydrofuryl, tetrahydrofurylmethylene, pyridyl, pyridylmethylene, naphthyl, naphthylmethylene, furyl, furylmethylene, thienyl, thienylmethylene, ##STR00516## that is unsubstituted or substituted by methyl; phenyl that is unsubstituted or substituted by methyl, dimethylamino, chloro, methoxy, trifluoromethyl or isopropyl; or benzyl that is unsubstituted or substituted by trifluoromethyl, bromo, chloro, fluoro, methoxy, cyano or methyl; R′ represents hydrogen, methyl, ethyl or difluoromethyl.

6. The R-pyridyloxycarboxylic acid and salt, ester derivative thereof according to claim 5, wherein the R-pyridyloxycarboxylic acid is selected from any one of Table 1 TABLE-US-00007 I No. A B C Q Y 1-1 F F F NH.sub.2 1-2 Cl Cl Cl CH.sub.3 NH.sub.2 1-3 Cl Cl H NH.sub.2 1-4 Cl Cl F NH.sub.2 1-5 Cl Cl CH.sub.3 CH.sub.3 NH.sub.2 1-6 Cl Cl CF.sub.3 NH.sub.2 1-7 CH.sub.3 CH.sub.3 F CH.sub.3 NH.sub.2 1-8 Et Et CF.sub.3 CH.sub.3 NH.sub.2 1-9 Cl H CH.sub.3 NH.sub.2 1-10 Cl Cl CH.sub.3 NH.sub.2 1-11 F CF.sub.3 CH.sub.3 NH.sub.2 1-12 Br Br F CH.sub.3 NH.sub.2 1-13 I I H CH.sub.3 NH.sub.2 1-14 F NH.sub.2 1-15 CF.sub.3 Cl F CH.sub.3 NH.sub.2 1-16 Cl CF.sub.3 H NH.sub.2 1-17 Cl Cl I CH.sub.3 NH.sub.2 1-18 Cl Br NH.sub.2 1-19 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 NH.sub.2 1-20 Cl CH.sub.3 F CH.sub.3 NH.sub.2 1-21 Cl CH.sub.3 H CH.sub.3 NH.sub.2 1-22 Cl F CH.sub.3 NH.sub.2 1-23 F F CF.sub.3 CH.sub.3 NH.sub.2 1-24 CH.sub.3 F CH.sub.3 NH.sub.2 1-25 Cl CH.sub.3 Br CH.sub.3 NH.sub.2 1-26 Cl Cl F CH.sub.3 NH.sub.2 1-27 Cl Cl F Et NH.sub.2 1-28 Cl Cl F NH.sub.2 1-29 Cl Cl F NH.sub.2 1-30 Cl Cl F NH.sub.2 1-31 Cl Cl F NH.sub.2 1-32 Cl Cl F NH.sub.2 1-33 Cl Cl F NH.sub.2 1-34 Cl Cl F NH.sub.2 1-35 Cl Cl F NH.sub.2 1-36 Cl Cl F F NH.sub.2 1-37 Cl Cl F Cl NH.sub.2 1-38 Cl Cl F Br NH.sub.2 1-39 Cl Cl F NH.sub.2 1-40 Cl Cl F NH.sub.2 1-41 Cl Cl F NH.sub.2 1-42 Cl Cl F NH.sub.2 1-43 Cl Cl F CF.sub.3 NH.sub.2 1-44 Cl Cl F NH.sub.2 1-45 Cl Cl F CN NH.sub.2 1-46 Cl Cl F NH.sub.2 1-47 Cl Cl F NH.sub.2 NH.sub.2 1-48 Cl Cl F NH.sub.2 1-49 Cl Cl F NH.sub.2 1-50 Cl Cl F NH.sub.2 1-51 Cl Cl F NO.sub.2 NH.sub.2 1-52 Cl Cl F NH.sub.2 1-53 Cl Cl F NH.sub.2 1-54 Cl Cl F NH.sub.2 1-55 Cl Cl F NH.sub.2 1-56 Cl Cl F NH.sub.2 1-57 Cl Cl F NH.sub.2 1-58 Cl Cl F NH.sub.2 1-59 Cl Cl F NH.sub.2 1-60 Cl Cl F NH.sub.2 1-61 Cl Cl F NH.sub.2 1-62 Cl Cl F NH.sub.2 1-63 Cl Cl F NH.sub.2 1-64 Cl Cl F NH.sub.2 1-65 Cl Cl F NH.sub.2 1-66 Cl Cl F NH.sub.2 1-67 Cl Cl F NH.sub.2 1-68 Cl Cl F CH.sub.3 1-69 Cl Cl F 1-70 Cl Cl F CH.sub.3 1-71 Cl Cl F CH.sub.3 1-72 Cl Cl F CH.sub.3 1-73 Cl Cl F CH.sub.3 or Table 2 TABLE-US-00008 I-1 No. A B C Q X Y salt/M 2-1  Cl Cl F O NH.sub.2 sodium salt 2-2  Cl Cl F CH.sub.3 S NH.sub.2 calcium salt 2-3  Cl Cl F CH.sub.3 O NH.sub.2 ammonium salt 2-4  Cl Cl F CH.sub.3 S NH.sub.2 tetramethylammonium salt 2-5  Cl Cl F Et O NH.sub.2 benzyltrimethylammonium salt 2-6  Cl Cl F O NH.sub.2 choline amine salt 2-7  Cl Cl F CH.sub.3 O NH.sub.2 dimethylamine salt 2-8  Cl Cl F O NH.sub.2 mono- isopropylamine salt 2-9  Cl Cl F Et S NH.sub.2 benzylamine salt 2-10  Cl Cl F Et O NH.sub.2 monoethanolamine salt 2-11  Cl Cl F O NH.sub.2 diglycolamine salt 2-12  Cl Cl F Et S NH.sub.2 diallylamine salt 2-13  Cl Cl F O NH.sub.2 cyclododecylamine salt 2-14  Cl Cl F CH.sub.3 O NH.sub.2 dimethylmonoethanolamine salt 2-15  Cl Cl F O NH.sub.2 diethylenetriamine salt 2-16  Cl Cl F O NH.sub.2 dimethylaminopropylamine salt 2-17  Cl Cl F CH.sub.3 S NH.sub.2 1,2-propyldiamine salt 2-18  Cl Cl F Et S NH.sub.2 triethylenetramine salt 2-19  Cl Cl F O NH.sub.2 N,N-bis[aminopropyl]methylamine salt 2-20  Cl Cl F S NH.sub.2 2-methylthiopropylamine salt 2-21  Cl Cl F O NH.sub.2 2-butoxyethylamine salt 2-22  Cl Cl F CH.sub.3 O NH.sub.2 AEPD salt 2-23  Cl Cl F O NH.sub.2 tri(methylol)aminomethane salt 2-24  Cl Cl F CH.sub.3 O NH.sub.2 morpholine salt 2-25  Cl Cl F Et S NH.sub.2 aminopropyl morpholine salt 2-26  Cl Cl F CH.sub.3 S NH.sub.2 Jeff amine D-230 salt 2-27  Cl Cl F Et O NH.sub.2 the salt of 2,4,6-tri(dimethylaminomethyl) phenol and sodium hydroxide 2-28  Cl CH.sub.3 H CH.sub.3 O NH.sub.2 CH.sub.3 2-29  Cl CH.sub.3 F CH.sub.3 O NH.sub.2 CH.sub.3 2-30  Cl Cl H CH.sub.3 O NH.sub.2 CH.sub.3 2-31  Cl Cl Cl CH.sub.3 O NH.sub.2 CH.sub.3 2-32  Cl Cl CH.sub.3 CH.sub.3 O NH.sub.2 CH.sub.3 2-33  Cl Cl F Et S NH.sub.2 CH.sub.3 2-34  Cl Cl F Et O NH.sub.2 CH.sub.3 2-35  Cl Cl F O NH.sub.2 CH.sub.3 2-36  Cl Cl F S NH.sub.2 CH.sub.3 2-37  Cl Cl F O NH.sub.2 CH.sub.3 2-38  Cl Cl F O NH.sub.2 CH.sub.3 2-39  Cl Cl F CF.sub.3 O NH.sub.2 CH.sub.3 2-40  Cl Cl F O NH.sub.2 CH.sub.3 2-41  Cl Cl F O NH.sub.2 CH.sub.3 2-42  Cl Cl F O NH.sub.2 CH.sub.3 2-43  Cl Cl F O NH.sub.2 CH.sub.3 2-44  Cl Cl F O NH.sub.2 CH.sub.3 2-45  Cl Cl F O NH.sub.2 CH.sub.3 2-46  Cl Cl F O NH.sub.2 CH.sub.3 2-47  Cl Cl F O NH.sub.2 CH.sub.3 2-48  Cl Cl F O NH.sub.2 CH.sub.3 2-49  Cl Cl F O NH.sub.2 CH.sub.3 2-50  Cl Cl F NO.sub.2 O NH.sub.2 CH.sub.3 2-51  Cl Cl F F O NH.sub.2 CH.sub.3 2-52  Cl Cl F Br O NH.sub.2 CH.sub.3 2-53  Cl Cl F Cl O NH.sub.2 CH.sub.3 2-54  Cl Cl F NH.sub.2 CH.sub.3 2-55  Cl Cl F O NH.sub.2 CH.sub.3 2-56  Cl Cl F NH.sub.2 O NH.sub.2 CH.sub.3 2-57  Cl Cl F O NH.sub.2 CH.sub.3 2-58  Cl Cl F O NH.sub.2 CH.sub.3 2-59  Cl Cl F O NH.sub.2 CH.sub.3 2-60  Cl Cl F O NH.sub.2 CH.sub.3 2-61  Cl Cl F CN O NH.sub.2 CH.sub.3 2-62  Cl Cl F O NH.sub.2 CH.sub.3 2-63  Cl Cl F O NH.sub.2 CH.sub.3 2-64  Cl Cl F O NH.sub.2 CH.sub.3 2-65  Cl Cl F O NH.sub.2 CH.sub.3 2-66  Cl Cl F O NH.sub.2 CH.sub.3 2-67  Cl Cl F O NH.sub.2 CH.sub.3 2-68  Cl Cl F O NH.sub.2 CH.sub.3 2-69  Cl Cl F CH.sub.3 O NH.sub.2 CH.sub.3 2-70  Cl Cl F CH.sub.3 S NH.sub.2 CH.sub.3 2-71  Cl Cl F CH.sub.3 O NH.sub.2 Et 2-72  Cl Cl F CH.sub.3 S NH.sub.2 Et 2-73  Cl Cl F CH.sub.3 O NH.sub.2 2-74  Cl Cl F CH.sub.3 S NH.sub.2 2-75  Cl Cl F CH.sub.3 O NH 2-76  Cl Cl F CH.sub.3 S NH.sub.2 2-77  Cl Cl F CH.sub.3 O NH.sub.2 2-78  Cl Cl F CH.sub.3 S NH.sub.2 2-79  Cl Cl F CH.sub.3 O NH.sub.2 2-80  Cl Cl F CH.sub.3 S NH.sub.2 2-81  Cl Cl F CH.sub.3 O NH.sub.2 2-82  Cl Cl F CH.sub.3 S NH.sub.2 2-83  Cl Cl F CH.sub.3 O NH.sub.2 2-84  Cl Cl F CH.sub.3 S NH.sub.2 2-85  Cl Cl F CH.sub.3 O NH.sub.2 2-86  Cl Cl F CH.sub.3 S NH.sub.2 2-87  Cl Cl F CH.sub.3 O NH.sub.2 2-88  Cl Cl F CH.sub.3 S NH.sub.2 2-89  Cl Cl F CH.sub.3 O NH.sub.2 2-90  Cl Cl F CH.sub.3 S NH.sub.2 2-91  Cl Cl F CH.sub.3 O NH.sub.2 2-92  Cl Cl F CH.sub.3 S NH.sub.2 2-93  Cl Cl F CH.sub.3 O NH.sub.2 2-94  Cl Cl F CH.sub.3 S NH.sub.2 2-95  Cl Cl F CH.sub.3 O NH.sub.2 2-96  Cl Cl F CH.sub.3 S NH.sub.2 2-97  Cl Cl F CH.sub.3 O NH.sub.2 2-98  Cl Cl F CH.sub.3 S NH.sub.2 2-99  Cl Cl F CH.sub.3 O NH.sub.2 2-100 Cl Cl F CH.sub.3 S NH.sub.2 2-101 Cl Cl F CH.sub.3 O NH.sub.2 2-102 Cl Cl F CH.sub.3 S NH.sub.2 2-103 Cl Cl F CH.sub.3 O NH.sub.2 2-104 Cl Cl F CH.sub.3 S NH.sub.2 2-105 Cl Cl F CH.sub.3 O NH.sub.2 2-106 Cl Cl F CH.sub.3 S NH.sub.2 2-107 Cl Cl F CH.sub.3 O NH.sub.2 2-108 Cl Cl F CH.sub.3 S NH.sub.2 2-109 Cl Cl F CH.sub.3 O NH.sub.2 2-110 Cl Cl F CH.sub.3 S NH.sub.2 2-111 Cl Cl F CH.sub.3 O NH.sub.2 2-112 Cl Cl F CH.sub.3 S NH.sub.2 2-113 Cl Cl F CH.sub.3 O NH.sub.2 2-114 Cl Cl F CH.sub.3 S NH.sub.2 2-115 Cl Cl F CH.sub.3 O NH.sub.2 2-116 Cl Cl F CH.sub.3 S NH.sub.2 2-117 Cl Cl F CH.sub.3 O NH.sub.2 2-118 Cl Cl F CH.sub.3 S NH.sub.2 2-119 Cl Cl F CH.sub.3 O NH.sub.2 2-120 Cl Cl F CH.sub.3 S NH.sub.2 2-121 Cl Cl F CH.sub.3 O NH.sub.2 2-122 Cl Cl F CH.sub.3 S NH.sub.2 2-123 Cl Cl F CH.sub.3 O NH.sub.2 2-124 Cl Cl F CH.sub.3 S NH.sub.2 2-125 Cl Cl F CH.sub.3 O NH.sub.2 2-126 Cl Cl F CH.sub.3 S NH.sub.2 2-127 Cl Cl F CH.sub.3 O NH.sub.2 2-128 Cl Cl F CH.sub.3 S NH.sub.2 2-129 Cl Cl F CH.sub.3 O NH.sub.2 2-130 Cl Cl F CH.sub.3 S NH.sub.2 2-131 Cl Cl F CH.sub.3 O NH.sub.2 2-132 Cl Cl F CH.sub.3 S NH.sub.2 2-133 Cl Cl F CH.sub.3 O NH.sub.2 2-134 Cl Cl F CH.sub.3 S NH.sub.2 2-135 Cl Cl F CH.sub.3 O NH.sub.2 2-136 Cl Cl F CH.sub.3 S NH.sub.2 2-137 Cl Cl F CH.sub.3 O NH.sub.2 2-138 Cl Cl F CH.sub.3 S NH.sub.2 2-139 Cl Cl F CH.sub.3 O NH.sub.2 2-140 Cl Cl F CH.sub.3 S NH.sub.2 2-141 Cl Cl F CH.sub.3 O NH.sub.2 2-142 Cl Cl F CH.sub.3 S NH.sub.2 2-143 Cl Cl F CH.sub.3 O NH.sub.2 2-144 Cl Cl F CH.sub.3 S NH.sub.2 2-145 Cl Cl F CH.sub.3 O NH.sub.2 2-146 Cl Cl F CH.sub.3 S NH.sub.2 2-147 Cl Cl F CH.sub.3 O NH.sub.2 2-148 Cl Cl F CH.sub.3 S NH.sub.2 2-149 Cl Cl F CH.sub.3 O NH.sub.2 2-150 Cl Cl F CH.sub.3 S NH.sub.2 2-151 Cl Cl F CH.sub.3 O NH.sub.2 2-152 Cl Cl F CH.sub.3 S NH.sub.2 2-153 Cl Cl F CH.sub.3 O NH.sub.2 2-154 Cl Cl F CH.sub.3 S NH.sub.2 2-155 Cl Cl F CH.sub.3 O NH.sub.2 2-156 Cl Cl F CH.sub.3 S NH.sub.2 2-157 Cl Cl F CH.sub.3 O NH.sub.2 2-158 Cl Cl F CH.sub.3 S NH.sub.2 2-159 Cl Cl F CH.sub.3 O NH.sub.2 2-160 Cl Cl F CH.sub.3 S NH.sub.2 2-161 Cl Cl F CH.sub.3 O NH.sub.2 2-162 Cl Cl F CH.sub.3 S NH.sub.2 2-163 Cl Cl F CH.sub.3 O NH.sub.2 2-164 Cl Cl F CH.sub.3 S NH.sub.2 2-165 Cl Cl F CH.sub.3 O NH.sub.2 2-166 Cl Cl F CH.sub.3 S NH.sub.2 2-167 Cl Cl F CH.sub.3 O NH.sub.2 2-168 Cl Cl F CH.sub.3 S NH.sub.2 2-169 Cl Cl F CH.sub.3 O NH.sub.2 2-170 Cl Cl F CH.sub.3 S NH.sub.2 2-171 Cl Cl F CH.sub.3 O NH.sub.2 2-172 Cl Cl F CH.sub.3 S NH.sub.2 2-173 Cl Cl F CH.sub.3 O NH.sub.2 2-174 Cl Cl F CH.sub.3 S NH.sub.2 2-175 Cl Cl F CH.sub.3 O NH.sub.2 2-176 Cl Cl F CH.sub.3 S NH.sub.2 2-177 Cl Cl F CH.sub.3 O NH.sub.2 2-178 Cl Cl F CH.sub.3 S NH.sub.2 2-179 Cl Cl F CH.sub.3 O NH.sub.2 2-180 Cl Cl F CH.sub.3 S NH.sub.2 2-181 Cl Cl F CH.sub.3 O NH.sub.2 2-182 Cl Cl F CH.sub.3 S NH.sub.2 2-183 Cl Cl F CH.sub.3 O NH.sub.2 2-184 Cl Cl F CH.sub.3 S NH.sub.2 2-185 Cl Cl F CH.sub.3 O NH.sub.2 2-186 Cl Cl F CH.sub.3 S NH.sub.2 2-187 Cl Cl F CH.sub.3 O NH.sub.2 2-188 Cl Cl F CH.sub.3 S NH.sub.2 2-189 Cl Cl F CH.sub.3 O NH.sub.2 2-190 Cl Cl F CH.sub.3 S NH.sub.2 2-191 Cl Cl F CH.sub.3 O NH.sub.2 2-192 Cl Cl F CH.sub.3 S NH.sub.2 2-193 Cl Cl F CH.sub.3 O NH.sub.2 2-194 Cl Cl F CH.sub.3 S NH.sub.2 2-195 Cl Cl F CH.sub.3 O NH.sub.2 2-196 Cl Cl F CH.sub.3 S NH.sub.2 2-197 Cl Cl F CH.sub.3 O NH.sub.2 2-198 Cl Cl F CH.sub.3 S NH.sub.2 2-199 Cl Cl F CH.sub.3 O NH.sub.2 2-200 Cl Cl F CH.sub.3 S NH.sub.2 2-201 Cl Cl F CH.sub.3 O NH.sub.2 2-202 Cl Cl F CH.sub.3 S NH.sub.2 2-203 Cl Cl F CH.sub.3 O NH.sub.2 2-204 Cl Cl F CH.sub.3 S NH.sub.2 2-205 Cl Cl F CH.sub.3 O NH.sub.2 2-206 Cl Cl F CH.sub.3 S NH.sub.2 2-207 Cl Cl F CH.sub.3 O NH.sub.2 2-208 Cl Cl F CH.sub.3 S NH.sub.2 2-209 Cl Cl F CH.sub.3 O NH.sub.2 2-210 Cl Cl F CH.sub.3 S NH.sub.2 2-211 Cl Cl F CH.sub.3 O NH.sub.2 2-212 Cl Cl F CH.sub.3 S NH.sub.2 2-213 Cl Cl F CH.sub.3 S NH.sub.2 2-214 Cl Cl F CH.sub.3 S NH.sub.2 2-215 Cl Cl F CH.sub.3 O NH.sub.2 2-216 Cl Cl F CH.sub.3 S NH.sub.2 2-217 Cl Cl F CH.sub.3 O NH.sub.2 2-218 Cl Cl F CH.sub.3 S NH.sub.2 2-219 Cl Cl F CH.sub.3 O NH.sub.2 2-220 Cl Cl F CH.sub.3 S NH.sub.2 2-221 Cl Cl F CH.sub.3 O NH.sub.2 2-222 Cl Cl F CH.sub.3 S NH.sub.2 2-223 Cl Cl F CH.sub.3 O NH.sub.2 2-224 Cl Cl F CH.sub.3 S NH.sub.2 2-225 Cl Cl F CH.sub.3 O NH.sub.2 2-226 Cl Cl F CH.sub.3 S NH.sub.2 2-227 Cl Cl F CH.sub.3 O NH.sub.2 2-228 Cl Cl F CH.sub.3 S NH.sub.2 2-229 Cl Cl F CH.sub.3 O NH.sub.2 2-230 Cl Cl F CH.sub.3 S NH.sub.2 2-231 Cl Cl F CH.sub.3 O NH.sub.2 2-232 Cl Cl F CH.sub.3 S NH.sub.2 2-233 Cl Cl F CH.sub.3 O NH.sub.2 2-234 Cl Cl F CH.sub.3 S NH.sub.2 2-235 Cl Cl F CH.sub.3 O NH.sub.2 2-236 Cl Cl F CH.sub.3 S NH.sub.2 2-237 Cl Cl F CH.sub.3 O NH.sub.2 2-238 Cl Cl F CH.sub.3 S NH.sub.2 2-239 Cl Cl F CH.sub.3 O NH.sub.2 2-240 Cl Cl F CH.sub.3 S NH.sub.2 2-241 Cl Cl F CH.sub.3 O NH.sub.2 2-242 Cl Cl F CH.sub.3 S NH.sub.2 2-243 Cl Cl F CH.sub.3 O NH.sub.2 2-244 Cl Cl F CH.sub.3 S NH.sub.2 2-245 Cl Cl F CH.sub.3 O NH.sub.2 2-246 Cl Cl F CH.sub.3 S NH.sub.2 2-247 Cl Cl F CH.sub.3 O NH.sub.2 2-248 Cl Cl F CH.sub.3 S NH.sub.2 2-249 Cl Cl F CH.sub.3 O NH.sub.2 2-250 Cl Cl F CH.sub.3 S NH.sub.2 2-251 Cl Cl F CH.sub.3 O NH.sub.2 2-252 Cl Cl F CH.sub.3 S NH.sub.2 2-253 Cl Cl F CH.sub.3 O NH.sub.2 2-254 Cl Cl F CH.sub.3 S NH.sub.2 2-255 Cl Cl F CH.sub.3 O NH.sub.2 2-256 Cl Cl F CH.sub.3 S NH.sub.2 2-257 Cl Cl F CH.sub.3 O NH.sub.2 2-258 Cl Cl F CH.sub.3 S NH.sub.2 2-259 Cl Cl F CH.sub.3 O NH.sub.2 2-260 Cl Cl F CH.sub.3 S NH.sub.2 2-261 Cl Cl F CH.sub.3 O NH.sub.2 2-262 Cl Cl F CH.sub.3 S NH.sub.2 2-263 Cl Cl F CH.sub.3 O NH.sub.2 2-264 Cl Cl F CH.sub.3 O NH.sub.2 2-265 Cl Cl F CH.sub.3 O NH.sub.2 2-266 Cl Cl F CH.sub.3 S NH.sub.2 2-267 Cl Cl F CH.sub.3 O NH.sub.2 2-268 Cl Cl F CH.sub.3 O NH.sub.2 2-269 Cl Cl F CH.sub.3 O NH.sub.2 2-270 Cl Cl CH.sub.3 CH.sub.3 O NH.sub.2 2-271 Cl Cl F CH.sub.3 O NH.sub.2 2-272 Cl Cl F CH.sub.3 S NH.sub.2 2-273 Cl Cl F CH.sub.3 O NH.sub.2 2-274 Cl Cl F CH.sub.3 S NH.sub.2 2-275 Cl Cl F CH.sub.3 O NH.sub.2 2-276 Cl Cl F CH.sub.3 O NH.sub.2 2-277 Cl Cl F CH.sub.3 O NH.sub.2 2-278 Cl Cl F CH.sub.3 O NH.sub.2 2-279 Cl Cl F CH.sub.3 O NH.sub.2 2-280 Cl Cl F CH.sub.3 O NH.sub.2 2-281 Cl Cl F CH.sub.3 O NH.sub.2 2-282 Cl Cl F CH.sub.3 O NH.sub.2 2-283 Cl Cl F CH.sub.3 O NH.sub.2 2-284 Cl Cl F CH.sub.3 O NH.sub.2 2-285 Cl Cl F CH.sub.3 O NH.sub.2 2-286 Cl Cl F CH.sub.3 O NH.sub.2 2-287 Cl Cl F CH.sub.3 O NH.sub.2 2-288 Cl Cl F CH.sub.3 O NH.sub.2 2-289 Cl Cl F CH.sub.3 O NH.sub.2 2-290 Cl Cl F CH.sub.3 S NH.sub.2 2-291 Cl Cl F CH.sub.3 O NH.sub.2 2-292 Cl Cl F CH.sub.3 O NH.sub.2 2-293 Cl Cl F CH.sub.3 O NH.sub.2 2-294 Cl Cl F CH.sub.3 O NH.sub.2 2-295 Cl Cl F CH.sub.3 O NH.sub.2 2-296 Cl Cl F CH.sub.3 O NH.sub.2 2-297 Cl Cl F CH.sub.3 O NH.sub.2 2-298 Cl Cl F CH.sub.3 O NH.sub.2 2-299 Cl Cl F CH.sub.3 O NH.sub.2 2-300 Cl Cl F CH.sub.3 O NH.sub.2 2-301 Cl Cl F CH.sub.3 S NH.sub.2 2-302 Cl Cl F CH.sub.3 O NH.sub.2 2-303 Cl Cl F CH.sub.3 S NH.sub.2 2-304 Cl Cl F CH.sub.3 O NH.sub.2 2-305 Cl Cl F CH.sub.3 S NH.sub.2 2-306 Cl Cl F CH.sub.3 O NH.sub.2 2-307 Cl Cl F CH.sub.3 S NH.sub.2 2-308 Cl Cl F CH.sub.3 O NH.sub.2 2-309 Cl Cl F CH.sub.3 S NH.sub.2 2-310 Cl Cl F CH.sub.3 O NH.sub.2 2-311 Cl Cl F CH.sub.3 S NH.sub.2 2-312 Cl Cl F CH.sub.3 O NH.sub.2 2-313 Cl Cl F CH.sub.3 S NH.sub.2 2-314 Cl Cl F CH.sub.3 O NH.sub.2 2-315 Cl Cl F CH.sub.3 S NH.sub.2 2-316 Cl Cl F CH.sub.3 O NH.sub.2 2-317 Cl Cl F CH.sub.3 S NH.sub.2 2-318 Cl Cl F CH.sub.3 O NH.sub.2 2-319 Cl Cl F CH.sub.3 S NH.sub.2 2-320 Cl Cl F CH.sub.3 O NH.sub.2 2-321 Cl Cl F CH.sub.3 S NH.sub.2 2-322 Cl Cl F CH.sub.3 O NH.sub.2 2-323 Cl Cl F CH.sub.3 S NH.sub.2 2-324 Cl Cl F CH.sub.3 O NH.sub.2 2-325 Cl Cl F CH.sub.3 S NH.sub.2 2-326 Cl Cl F Et O NH.sub.2 2-327 Cl Cl F CH.sub.3 O NH.sub.2 2-328 Cl Cl F CH.sub.3 S NH.sub.2 2-329 Cl Cl F CH.sub.3 O NH.sub.2 2-330 Cl Cl F CH.sub.3 S NH.sub.2 2-331 Cl Cl F CH.sub.3 O NH.sub.2 2-332 Cl Cl F CH.sub.3 S NH.sub.2 2-333 Cl Cl F CH.sub.3 O NH.sub.2 2-334 Cl Cl F CH.sub.3 S NH.sub.2 2-335 Cl Cl F CH.sub.3 O NH.sub.2 2-336 Cl Cl F CH.sub.3 S NH.sub.2 2-337 Cl Cl F CH.sub.3 O NH.sub.2 2-338 Cl Cl F CH.sub.3 S NH.sub.2 2-339 Cl Cl F CH.sub.3 S NH.sub.2 2-340 Cl Cl F CH.sub.3 O NH.sub.2 2-341 Cl Cl F CH.sub.3 O NH.sub.2 2-342 Cl Cl F CH.sub.3 O NH.sub.2 2-343 Cl Cl F CH.sub.3 S NH.sub.2 2-344 Cl Cl F CH.sub.3 S NH.sub.2 2-345 Cl Cl F CH.sub.3 S NH.sub.2 2-346 Cl Cl F CH.sub.3 O NH.sub.2 2-347 Cl Cl F CH.sub.3 S NH.sub.2 2-348 Cl Cl F CH.sub.3 O NH.sub.2 2-349 Cl Cl F CH.sub.3 O NH.sub.2 2-350 Cl Cl F CH.sub.3 O NH.sub.2 2-351 Cl Cl F CH.sub.3 O NH.sub.2 2-352 Cl Cl F CH.sub.3 O NH.sub.2 2-353 Cl Cl F CH.sub.3 O NH.sub.2 2-354 Cl Cl F CH.sub.3 O NH.sub.2 2-355 Cl Cl F CH.sub.3 O NH.sub.2 2-356 Cl Cl F CH.sub.3 O NH.sub.2 2-357 Cl Cl F CH.sub.3 S NH.sub.2 2-358 Cl Cl F CH.sub.3 S NH.sub.2 2-359 Cl Cl F CH.sub.3 O NH.sub.2 2-360 Cl Cl F CH.sub.3 S NH.sub.2 2-361 Cl Cl F CH.sub.3 O NH.sub.2 2-362 Cl Cl F CH.sub.3 O NH.sub.2 2-363 Cl Cl F CH.sub.3 S NH.sub.2 2-364 Cl Cl F CH.sub.3 O NH.sub.2 2-365 Cl Cl F CH.sub.3 S NH.sub.2 2-366 Cl Cl F CH.sub.3 O NH.sub.2 2-367 Cl Cl F CH.sub.3 O NH.sub.2 2-368 Cl Cl F CH.sub.3 S NH.sub.2 2-369 Cl Cl F CH.sub.3 O NH.sub.2 2-370 Cl Cl F CH.sub.3 O NH.sub.2 2-371 Cl Cl F CH.sub.3 O NH.sub.2 2-372 Cl Cl F CH.sub.3 O NH.sub.2 2-373 Cl Cl F CH.sub.3 S NH.sub.2 2-374 Cl Cl F CH.sub.3 O NH.sub.2 2-375 Cl Cl F CH.sub.3 O CH.sub.3 2-376 Cl Cl F CH.sub.3 S CH.sub.3 2-377 Cl Cl F CH.sub.3 O CH.sub.3 2-378 Cl Cl F CH.sub.3 O CH.sub.3 2-379 Cl Cl F CH.sub.3 O CH.sub.3 2-380 Cl Cl F CH.sub.3 O CH.sub.3 2-381 Cl Cl F CH.sub.3 O CH.sub.3 2-382 Cl Cl F O NH.sub.2 Et 2-383 Cl Cl F O NH.sub.2 Et 2-384 Cl Cl F Et O NH.sub.2 2-385 Cl Cl F S NH.sub.2 CH.sub.3 2-386 Cl Cl CH.sub.3 CH.sub.3 O NH.sub.2 2-387 Cl Cl F CH.sub.3 O CH.sub.3

7. A preparation method of the R-pyridyloxycarboxylic acid and salt, ester derivative thereof according to claim 1, comprising: reacting a compound of formula III with a compound of formula II to obtain a compound of formula I-1-1 as follows: ##STR00927## wherein: W represents an alkali metal; Hal represents halogen; the reaction is carried out in the presence of a catalyst and a solvent; reacting the compound of formula I-1-1 in the presence of a lithium hydroxide aqueous solution and a solvent to obtain a compound of formula I as follows: ##STR00928## reacting the compound of formula I with M-SH to obtain a compound of formula I-1-2 as follows: ##STR00929## wherein: the reaction is carried out in the presence of a dehydrant and a solvent, or, when Y represents NR.sub.1R.sub.2, wherein R.sub.1 and R.sub.2 are not hydrogen concurrently, which is obtained by reacting a compound of formula I-2 ##STR00930## or a compound of formula I-1-3 ##STR00931## with a corresponding halide.

8. A herbicidal composition comprising (i) at least one of an R-type pyridyloxycarboxylic acid and salt, ester derivative thereof according to claim 1.

9. A method for controlling a weed comprising applying a herbicidally effective amount of at least one of the R-type pyridyloxycarboxylic acid and salt, ester derivative thereof according to claim 1.

10. A method for controlling a weed, comprising applying the R-pyridyloxycarboxylic acid and salt, ester derivative thereof according to claim 1 in a useful crop, wherein the useful crop is a genetically modified crop or a crop treated by gene editing technology.

11. The R-pyridyloxycarboxylic acid and salt, ester derivative thereof according to claim 5, wherein the salt is alkali metal salt, alkaline earth metal salt, heavy metal salt, aluminum salt, ammonium salt, tetramethylammonium salt, tetraethylammonium salt, tetrapropylammonium salt, tetraisopropylammonium salt, tetrabutylammonium salt, benzyltrimethylammonium salt, benzyltriethylammonium salt, choline amine salt, monomethylamine salt, dimethylamine salt, trimethylamine salt, monoethylamine salt, diethylamine salt, triethylamine salt, monoisopropylamine salt, diisopropylamine salt, triisopropylamine salt, monoisobutylamine salt, pentylamine salt, hexylamine salt, heptylamine salt, dodecylamine salt, tetradecylamine salt, diallylamine salt, cyclododecylamine salt, benzylamine salt, monoethanolamine salt, diethanolamine salt, triethanolamine salt, tripropanolamine salt, triisopropanolamine salt, tri(2-hydroxypropyl)amine salt, methylmonoethanolamine salt, dimethylmonoethanolamine salt, methyldiethanolamine salt, diethylethanolamine salt, diglycolamine salt, diethylenetriamine salt, dimethylaminopropylamine salt, 1,2-propyldiamine salt, triethylenetetramine salt, N,N-bis[aminopropyl]methylamine salt, 2-methylthiopropylamine salt, 2-butoxyethylamine salt, AEPD salt, tri(methylol) aminomethane salt, morpholine salt, aminopropyl morpholine salt, Jeff amine D-230 salt, or the salt of 2,4,6-tri(dimethylaminomethyl) phenol and sodium hydroxide.

12. The preparation method according to claim 7, wherein W is K or Na; Hal is Br or Cl; or the reaction is carried out in the presence of a catalyst and a solvent, wherein the catalyst is TBAB, and the solvent is one or more selected from the group consisting of DCM, DCE, ACN, THF, and DMF.

13. The preparation method according to claim 7, wherein in the step of reacting the compound of formula I-1-1 in the presence of a lithium hydroxide aqueous solution and a solvent to obtain a compound of formula I, the solvent is one or more selected from the group consisting of methanol, ethanol, and isopropanol.

14. The preparation method according to claim 7, wherein in the step of reacting the compound of formula I with M-SH to obtain a compound of formula I-1-2, the dehydrant is DCC, and the solvent is one or more selected from the group consisting of dichloromethane, dichloroethane, acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, tetrahydrofuran, toluene, and xylene.

15. The preparation method according to claim 7, wherein in the step of reacting a compound of formula I-2 or a compound of formula I-1-3 with a corresponding halide, the halide is chloride or bromide, the reaction is carried out in the presence of a base and a solvent, and a catalyst is optionally added during the reaction.

16. The preparation method according to claim 15, wherein the base is one or more selected from the group consisting of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate and cesium carbonate; the solvent is one or more selected from the group consisting of THF, 1,4-dioxane, toluene, 1,2-dichloroethane, ethyl acetate, acetonitrile, DMF, acetone, dichloromethane and chloroform; and the catalyst is DMAP.

17. The herbicidal composition according to claim 8, further comprising one or more additional herbicides and/or safeners.

18. The herbicidal composition according to claim 8, further comprising agrochemically acceptable formulation auxiliaries.

19. The method according to claim 9, wherein the plant is rice, and the weed is a gramineous weed selected from the group consisting of Echinochloa crusgalli, Digitaria sanguinalis, and Semen euphorbiae Lathyridis or a broad-leaved weed selected from the group consisting of Monochoria Vaginalis, Abutilon theophrasti Medic., and Galium aparine.

20. The method according to claim 10, wherein the crop is rice, and the weed is a gramineous weed selected from the group consisting of Echinochloa crusgalli, Digitaria sanguinalis, and Semen euphorbiae Lathyridis, or a broad-leaved weed selected from the group consisting of Monochoria Vaginalis, Abutilon theophrasti Medic., and Galium aparine.

Description

SPECIFIC MODE FOR CARRYING OUT THE INVENTION

[0142] The following examples are intended to illustrate the present invention and should not be construed as limiting the present invention in any way. The scope for which protection is sought in the present invention is intended to be defined by the claims.

[0143] In view of economics and variety of a compound, we preferably synthesized several compounds, part of which are listed in the following Tables 1-2. The structure and information of a certain compound are shown in Tables 1-3. The compounds in Tables 1-2 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 The structure of compounds (R configuration) [00056] No. A B C Q Y 1-1  F F F [00057] NH.sub.2 1-2  Cl Cl Cl CH.sub.3 NH.sub.2 1-3  Cl Cl H [00058] NH.sub.2 1-4  Cl Cl F [00059] NH.sub.2 1-5  Cl Cl CH.sub.3 CH.sub.3 NH.sub.2 1-6  Cl Cl CF.sub.3 [00060] NH.sub.2 1-7  CH.sub.3 CH.sub.3 F CH.sub.3 NH.sub.2 1-8  Et Et CF.sub.3 CH.sub.3 NH.sub.2 1-9  [00061] CI H CH.sub.3 NH.sub.2 1-10 [00062] Cl Cl CH.sub.3 NH.sub.2 1-11 F [00063] CF.sub.3 CH.sub.3 NH.sub.2 1-12 Br Br F CH.sub.3 NH.sub.2 1-13 I I H CH.sub.3 NH.sub.2 1-14 [00064] [00065] F [00066] NH.sub.2 1-15 CF.sub.3 Cl F CH.sub.3 NH.sub.2 1-16 Cl CF.sub.3 H [00067] NH.sub.2 1-17 Cl Cl I CH.sub.3 NH.sub.2 1-18 Cl [00068] Br [00069] NH.sub.2 1-19 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 NH.sub.2 1-20 Cl CH.sub.3 F CH.sub.3 NH.sub.2 1-21 Cl CH.sub.3 H CH.sub.3 NH.sub.2 1-22 Cl [00070] F CH.sub.3 NH.sub.2 1-23 F F CF.sub.3 CH.sub.3 NH.sub.2 1-24 CH.sub.3 [00071] F CH.sub.3 NH.sub.2 1-25 Cl CH.sub.3 Br CH.sub.3 NH.sub.2 1-26 Cl Cl F CH.sub.3 NH.sub.2 1-27 Cl Cl F Et NH.sub.2 1-28 Cl Cl F [00072] NH.sub.2 1-29 Cl Cl F [00073] NH.sub.2 1-30 Cl Cl F [00074] NH.sub.2 1-31 Cl Cl F [00075] NH.sub.2 1-32 Cl Cl F [00076] NH.sub.2 1-33 Cl Cl F [00077] NH.sub.2 1-34 Cl Cl F [00078] NH.sub.2 1-35 Cl Cl F [00079] NH.sub.2 1-36 Cl Cl F F NH.sub.2 1-37 Cl Cl F Cl NH.sub.2 1-38 Cl Cl F Br NH.sub.2 1-39 Cl Cl F [00080] NH.sub.2 1-40 Cl Cl F [00081] NH.sub.2 1-41 Cl Cl F [00082] NH.sub.2 1-42 Cl Cl F [00083] NH.sub.2 1-43 Cl Cl F CF.sub.3 NH.sub.2 1-44 Cl Cl F [00084] NH.sub.2 1-45 Cl Cl F CN NH.sub.2 1-46 Cl Cl F [00085] NH.sub.2 1-47 Cl Cl F NH.sub.2 NH.sub.2 1-48 Cl Cl F [00086] NH.sub.2 1-49 Cl Cl F [00087] NH.sub.2 1-50 Cl Cl F [00088] NH.sub.2 1-51 Cl Cl F NO.sub.2 NH.sub.2 1-52 Cl Cl F [00089] NH.sub.2 1-53 Cl Cl F [00090] NH.sub.2 1-54 Cl Cl F [00091] NH.sub.2 1-55 Cl Cl F [00092] NH.sub.2 1-56 Cl Cl F [00093] NH.sub.2 1-57 Cl Cl F [00094] NH.sub.2 1-58 Cl Cl F [00095] NH.sub.2 1-59 Cl Cl F [00096] NH.sub.2 1-60 Cl Cl F [00097] NH.sub.2 1-61 Cl Cl F [00098] NH.sub.2 1-62 Cl Cl F [00099] NH.sub.2 1-63 Cl Cl F [00100] NH.sub.2 1-64 Cl Cl F [00101] NH.sub.2 1-65 Cl Cl F [00102] NH.sub.2 1-66 Cl Cl F [00103] NH.sub.2 1-67 Cl Cl F [00104] NH.sub.2 1-68 Cl Cl F CH.sub.3 [00105] 1-69 Cl Cl F [00106] [00107] 1-70 Cl Cl F CH.sub.3 [00108] 1-71 Cl Cl F CH.sub.3 [00109] 1-72 Cl Cl F CH.sub.3 [00110] 1-73 Cl Cl F CH.sub.3 [00111]

TABLE-US-00002 TABLE 2 The structure of derivatives (R configuration) [00112] No. A B C Q X Y salt/M 2-1  Cl Cl F [00113] O NH.sub.2 sodium salt 2-2  Cl Cl F CH.sub.3 S NH.sub.2 calcium salt 2-3  Cl Cl F CH.sub.3 O NH.sub.2 ammonium salt 2-4  Cl Cl F CH.sub.3 S NH.sub.2 tetramethylammonium salt 2-5  Cl Cl F Et O NH.sub.2 benzyltrimethylammonium salt 2-6  Cl Cl F [00114] O NH.sub.2 choline amine salt 2-7  Cl Cl F CH.sub.3 O NH.sub.2 dimethylamine salt 2-8  Cl Cl F [00115] O NH.sub.2 monoisopropylamine salt 2-9  Cl Cl F Et S NH.sub.2 benzylamine salt 2-10  Cl Cl F Et O NH.sub.2 monoethanolamine salt 2-11  Cl Cl F [00116] O NH.sub.2 diglycolamine salt 2-12  Cl Cl F Et S NH.sub.2 diallylamine salt 2-13  Cl Cl F [00117] O NH.sub.2 cyclododecylamine salt 2-14  Cl Cl F CH.sub.3 O NH.sub.2 dimethylmonoethanolamine salt 2-15  Cl Cl F [00118] O NH.sub.2 diethylenetriamine salt 2-16  Cl Cl F [00119] O NH.sub.2 dimethylaminopropylamine salt 2-17  Cl Cl F CH.sub.3 S NH.sub.2 1,2-propyldiamine salt 2-18  Cl Cl F Et S NH.sub.2 triethylenetetramine salt 2-19  Cl Cl F [00120] O NH.sub.2 N,N-bis[aminopropyl]methylamine salt 2-20  Cl Cl F [00121] S NH.sub.2 2-methylthiopropylamine salt 2-21  Cl Cl F [00122] O NH.sub.2 2-butoxyethylamine salt 2-22  Cl Cl F CH.sub.3 O NH.sub.2 AEPD salt 2-23  Cl Cl F [00123] O NH.sub.2 tri(methylol) aminomethane salt 2-24  Cl Cl F CH.sub.3 O NH.sub.2 morpholine salt 2-25  Cl Cl F Et S NH.sub.2 aminopropyl morpholine salt 2-26  Cl Cl F CH.sub.3 S NH.sub.2 Jeff amine D-230 salt 2-27  Cl Cl F Et O NH.sub.2 the salt of 2,4,6-tri(dimethylaminomethyl) phenol and sodium hydroxide 2-28  Cl CH.sub.3 H CH.sub.3 O NH.sub.2 CH.sub.3 2-29  Cl CH.sub.3 F CH.sub.3 O NH.sub.2 CH.sub.3 2-30  Cl Cl H CH.sub.3 O NH.sub.2 CH.sub.3 2-31  Cl Cl Cl CH.sub.3 O NH.sub.2 CH.sub.3 2-32  Cl Cl CH.sub.3 CH.sub.3 O NH.sub.2 CH.sub.3 2-33  Cl Cl F Et S NH.sub.2 CH.sub.3 2-34  Cl Cl F Et O NH.sub.2 CH.sub.3 2-35  Cl Cl F [00124] O NH.sub.2 CH.sub.3 2-36  Cl Cl F [00125] S NH.sub.2 CH.sub.3 2-37  Cl Cl F [00126] O NH.sub.2 CH.sub.3 2-38  Cl Cl F [00127] O NH.sub.2 CH.sub.3 2-39  Cl Cl F CF.sub.3 O NH.sub.2 CH.sub.3 2-40  Cl Cl F [00128] O NH.sub.2 CH.sub.3 2-41  Cl Cl F [00129] O NH.sub.2 CH.sub.3 2-42  Cl Cl F [00130] O NH.sub.2 CH.sub.3 2-43  Cl Cl F [00131] O NH.sub.2 CH.sub.3 2-44  Cl Cl F [00132] O NH.sub.2 CH.sub.3 2-45  Cl Cl F [00133] O NH.sub.2 CH.sub.3 2-46  Cl Cl F [00134] O NH.sub.2 CH.sub.3 2-47  Cl Cl F [00135] O NH.sub.2 CH.sub.3 2-48  Cl Cl F [00136] O NH.sub.2 CH.sub.3 2-49  Cl Cl F [00137] O NH.sub.2 CH.sub.3 2-50  Cl Cl F NO.sub.2 O NH.sub.2 CH.sub.3 2-51  Cl Cl F F O NH.sub.2 CH.sub.3 2-52  Cl Cl F Br O NH.sub.2 CH.sub.3 2-53  Cl Cl F Cl O NH.sub.2 CH.sub.3 2-54  Cl Cl F [00138] NH.sub.2 CH.sub.3 2-55  Cl Cl F [00139] NH.sub.2 CH.sub.3 2-56  Cl Cl F NH.sub.2 O NH.sub.2 CH.sub.3 2-57  Cl Cl F [00140] O NH.sub.2 CH.sub.3 2-58  Cl Cl F [00141] O NH.sub.2 CH.sub.3 2-59  Cl Cl F [00142] O NH.sub.2 CH.sub.3 2-60  Cl Cl F [00143] O NH.sub.2 CH.sub.3 2-61  Cl Cl F CN O NH.sub.2 CH.sub.3 2-62  Cl Cl F [00144] O NH.sub.2 CH.sub.3 2-63  Cl Cl F [00145] O NH.sub.2 CH.sub.3 2-64  Cl Cl F [00146] O NH.sub.2 CH.sub.3 2-65  Cl Cl F [00147] O NH.sub.2 CH.sub.3 2-66  Cl Cl F [00148] O NH.sub.2 CH.sub.3 2-67  Cl Cl F [00149] O NH.sub.2 CH.sub.3 2-68  Cl Cl F [00150] O NH.sub.2 CH.sub.3 2-69  Cl Cl F CH.sub.3 O NH.sub.2 CH.sub.3 2-70  Cl Cl F CH.sub.3 S NH.sub.2 CH.sub.3 2-71  Cl Cl F CH.sub.3 O NH.sub.2 Et 2-72  Cl Cl F CH.sub.3 S NH.sub.2 Et 2-73  Cl Cl F CH.sub.3 O NH.sub.2 [00151] 2-74  Cl Cl F CH.sub.3 S NH.sub.2 [00152] 2-75  Cl Cl F CH.sub.3 O NH.sub.2 [00153] 2-76  Cl Cl F CH.sub.3 S NH.sub.2 [00154] 2-77  Cl Cl F CH.sub.3 O NH.sub.2 [00155] 2-78  Cl Cl F CH.sub.3 S NH.sub.2 [00156] 2-79  Cl Cl F CH.sub.3 O NH.sub.2 [00157] 2-80  Cl Cl F CH.sub.3 S NH.sub.2 [00158] 2-81  Cl Cl F CH.sub.3 O NH.sub.2 [00159] 2-82  Cl Cl F CH.sub.3 S NH.sub.2 [00160] 2-83  Cl Cl F CH.sub.3 O NH.sub.2 [00161] 2-84  Cl Cl F CH.sub.3 S NH.sub.2 [00162] 2-85  Cl Cl F CH.sub.3 O NH.sub.2 [00163] 2-86  Cl Cl F CH.sub.3 S NH.sub.2 [00164] 2-87  Cl Cl F CH.sub.3 O NH.sub.2 [00165] 2-88  Cl Cl F CH.sub.3 S NH.sub.2 [00166] 2-89  Cl Cl F CH.sub.3 O NH.sub.2 [00167] 2-90  Cl Cl F CH.sub.3 S NH.sub.2 [00168] 2-91  Cl Cl F CH.sub.3 O NH.sub.2 [00169] 2-92  Cl Cl F CH.sub.3 S NH.sub.2 [00170] 2-93  Cl Cl F CH.sub.3 O NH.sub.2 [00171] 2-94  Cl Cl F CH.sub.3 S NH.sub.2 [00172] 2-95  Cl Cl F CH.sub.3 O NH.sub.2 [00173] 2-96  Cl Cl F CH.sub.3 S NH.sub.2 [00174] 2-97  Cl Cl F CH.sub.3 O NH.sub.2 [00175] 2-98  Cl Cl F CH.sub.3 S NH.sub.2 [00176] 2-99  Cl Cl F CH.sub.3 O NH.sub.2 [00177] 2-100 Cl Cl F CH.sub.3 S NH.sub.2 [00178] 2-101 Cl Cl F CH.sub.3 O NH.sub.2 [00179] 2-102 Cl Cl F CH.sub.3 S NH.sub.2 [00180] 2-103 Cl Cl F CH.sub.3 O NH.sub.2 [00181] 2-104 Cl Cl F CH.sub.3 S NH.sub.2 [00182] 2-105 Cl Cl F CH.sub.3 O NH.sub.2 [00183] 2-106 Cl Cl F CH.sub.3 S NH.sub.2 [00184] 2-107 Cl Cl F CH.sub.3 O NH.sub.2 [00185] 2-108 Cl Cl F CH.sub.3 S NH.sub.2 [00186] 2-109 Cl Cl F CH.sub.3 O NH.sub.2 [00187] 2-110 Cl Cl F CH.sub.3 S NH.sub.2 [00188] 2-111 Cl Cl F CH.sub.3 O NH.sub.2 [00189] 2-112 Cl Cl F CH.sub.3 S NH.sub.2 [00190] 2-113 Cl Cl F CH.sub.3 O NH.sub.2 [00191] 2-114 Cl Cl F CH.sub.3 S NH.sub.2 [00192] 2-115 Cl Cl F CH.sub.3 O NH.sub.2 [00193] 2-116 Cl Cl F CH.sub.3 S NH.sub.2 [00194] 2-117 Cl Cl F CH.sub.3 O NH.sub.2 [00195] 2-118 Cl Cl F CH.sub.3 S NH.sub.2 [00196] 2-119 Cl Cl F CH.sub.3 O NH.sub.2 [00197] 2-120 Cl Cl F CH.sub.3 S NH.sub.2 [00198] 2-121 Cl Cl F CH.sub.3 O NH.sub.2 [00199] 2-122 Cl Cl F CH.sub.3 S NH.sub.2 [00200] 2-123 Cl Cl F CH.sub.3 O NH.sub.2 [00201] 2-124 Cl Cl F CH.sub.3 S NH.sub.2 [00202] 2-125 Cl Cl F CH.sub.3 O NH.sub.2 [00203] 2-126 Cl Cl F CH.sub.3 S NH.sub.2 [00204] 2-127 Cl Cl F CH.sub.3 O NH.sub.2 [00205] 2-128 Cl Cl F CH.sub.3 S NH.sub.2 [00206] 2-129 Cl Cl F CH.sub.3 O NH.sub.2 [00207] 2-130 Cl Cl F CH.sub.3 S NH.sub.2 [00208] 2-131 Cl Cl F CH.sub.3 O NH.sub.2 [00209] 2-132 Cl Cl F CH.sub.3 S NH.sub.2 [00210] 2-133 Cl Cl F CH.sub.3 O NH.sub.2 [00211] 2-134 Cl Cl F CH.sub.3 S NH.sub.2 [00212] 2-135 Cl Cl F CH.sub.3 O NH.sub.2 [00213] 2-136 Cl Cl F CH.sub.3 S NH.sub.2 [00214] 2-137 Cl Cl F CH.sub.3 O NH.sub.2 [00215] 2-138 Cl Cl F CH.sub.3 S NH.sub.2 [00216] 2-139 Cl Cl F CH.sub.3 O NH.sub.2 [00217] 2-140 Cl Cl F CH.sub.3 S NH.sub.2 [00218] 2-141 Cl Cl F CH.sub.3 O NH.sub.2 [00219] 2-142 Cl Cl F CH.sub.3 S NH.sub.2 [00220] 2-143 Cl Cl F CH.sub.3 O NH.sub.2 [00221] 2-144 Cl Cl F CH.sub.3 S NH.sub.2 [00222] 2-145 Cl Cl F CH.sub.3 O NH.sub.2 [00223] 2-146 Cl Cl F CH.sub.3 S NH.sub.2 [00224] 2-147 Cl Cl F CH.sub.3 O NH.sub.2 [00225] 2-148 Cl Cl F CH.sub.3 S NH.sub.2 [00226] 2-149 Cl Cl F CH.sub.3 O NH.sub.2 [00227] 2-150 Cl Cl F CH.sub.3 S NH.sub.2 [00228] 2-151 Cl Cl F CH.sub.3 O NH.sub.2 [00229] 2-152 Cl Cl F CH.sub.3 S NH.sub.2 [00230] 2-153 Cl Cl F CH.sub.3 O NH.sub.2 [00231] 2-154 Cl Cl F CH.sub.3 S NH.sub.2 [00232] 2-155 Cl Cl F CH.sub.3 O NH.sub.2 [00233] 2-156 Cl Cl F CH.sub.3 S NH.sub.2 [00234] 2-157 Cl Cl F CH.sub.3 O NH.sub.2 [00235] 2-158 Cl Cl F CH.sub.3 S NH.sub.2 [00236] 2-159 Cl Cl F CH.sub.3 O NH.sub.2 [00237] 2-160 Cl Cl F CH.sub.3 S NH.sub.2 [00238] 2-161 Cl Cl F CH.sub.3 O NH.sub.2 [00239] 2-162 Cl Cl F CH.sub.3 S NH.sub.2 [00240] 2-163 Cl Cl F CH.sub.3 O NH.sub.2 [00241] 2-164 Cl Cl F CH.sub.3 S NH.sub.2 [00242] 2-165 Cl Cl F CH.sub.3 O NH.sub.2 [00243] 2-166 Cl Cl F CH.sub.3 S NH.sub.2 [00244] 2-167 Cl Cl F CH.sub.3 O NH.sub.2 [00245] 2-168 Cl Cl F CH.sub.3 S NH.sub.2 [00246] 2-169 Cl Cl F CH.sub.3 O NH.sub.2 [00247] 2-170 Cl Cl F CH.sub.3 S NH.sub.2 [00248] 2-171 Cl Cl F CH.sub.3 O NH.sub.2 [00249] 2-172 Cl Cl F CH.sub.3 S NH.sub.2 [00250] 2-173 Cl Cl F CH.sub.3 O NH.sub.2 [00251] 2-174 Cl Cl F CH.sub.3 S NH.sub.2 [00252] 2-175 Cl Cl F CH.sub.3 O NH.sub.2 [00253] 2-176 Cl Cl F CH.sub.3 S NH.sub.2 [00254] 2-177 Cl Cl F CH.sub.3 O NH.sub.2 [00255] 2-178 Cl Cl F CH.sub.3 S NH.sub.2 [00256] 2-179 Cl Cl F CH.sub.3 O NH.sub.2 [00257] 2-180 Cl Cl F CH.sub.3 S NH.sub.2 [00258] 2-181 Cl Cl F CH.sub.3 O NH.sub.2 [00259] 2-182 Cl Cl F CH.sub.3 S NH.sub.2 [00260] 2-183 Cl Cl F CH.sub.3 O NH.sub.2 [00261] 2-184 Cl Cl F CH.sub.3 S NH.sub.2 [00262] 2-185 Cl Cl F CH.sub.3 O NH.sub.2 [00263] 2-186 Cl Cl F CH.sub.3 S NH.sub.2 [00264] 2-187 Cl Cl F CH.sub.3 O NH.sub.2 [00265] 2-188 Cl Cl F CH.sub.3 S NH.sub.2 [00266] 2-189 Cl Cl F CH.sub.3 O NH.sub.2 [00267] 2-190 Cl Cl F CH.sub.3 S NH.sub.2 [00268] 2-191 Cl Cl F CH.sub.3 O NH.sub.2 [00269] 2-192 Cl Cl F CH.sub.3 S NH.sub.2 [00270] 2-193 Cl Cl F CH.sub.3 O NH.sub.2 [00271] 2-194 Cl Cl F CH.sub.3 S NH.sub.2 [00272] 2-195 Cl Cl F CH.sub.3 O NH.sub.2 [00273] 2-196 Cl Cl F CH.sub.3 S NH.sub.2 [00274] 2-197 Cl Cl F CH.sub.3 O NH.sub.2 [00275] 2-198 Cl Cl F CH.sub.3 S NH.sub.2 [00276] 2-199 Cl Cl F CH.sub.3 O NH.sub.2 [00277] 2-200 Cl Cl F CH.sub.3 S NH.sub.2 [00278] 2-201 Cl Cl F CH.sub.3 O NH.sub.2 [00279] 2-202 Cl Cl F CH.sub.3 S NH.sub.2 [00280] 2-203 Cl Cl F CH.sub.3 O NH.sub.2 [00281] 2-204 Cl Cl F CH.sub.3 S NH.sub.2 [00282] 2-205 Cl Cl F CH.sub.3 O NH.sub.2 [00283] 2-206 Cl Cl F CH.sub.3 S NH.sub.2 [00284] 2-207 Cl Cl F CH.sub.3 O NH.sub.2 [00285] 2-208 Cl Cl F CH.sub.3 S NH.sub.2 [00286] 2-209 Cl Cl F CH.sub.3 O NH.sub.2 [00287] 2-210 Cl Cl F CH.sub.3 S NH.sub.2 [00288] 2-211 Cl Cl F CH.sub.3 O NH.sub.2 [00289] 2-212 Cl Cl F CH.sub.3 S NH.sub.2 [00290] 2-213 Cl Cl F CH.sub.3 O NH.sub.2 [00291] 2-214 Cl Cl F CH.sub.3 S NH.sub.2 [00292] 2-215 Cl Cl F CH.sub.3 O NH.sub.2 [00293] 2-216 Cl Cl F CH.sub.3 S NH.sub.2 [00294] 2-217 Cl Cl F CH.sub.3 O NH.sub.2 [00295] 2-218 Cl Cl F CH.sub.3 S NH.sub.2 [00296] 2-219 Cl Cl F CH.sub.3 O NH.sub.2 [00297] 2-220 Cl Cl F CH.sub.3 S NH.sub.2 [00298] 2-221 Cl Cl F CH.sub.3 O NH.sub.2 [00299] 2-222 Cl Cl F CH.sub.3 S NH.sub.2 [00300] 2-223 Cl Cl F CH.sub.3 O NH.sub.2 [00301] 2-224 Cl Cl F CH.sub.3 S NH.sub.2 [00302] 2-225 Cl Cl F CH.sub.3 O NH.sub.2 [00303] 2-226 Cl Cl F CH.sub.3 S NH.sub.2 [00304] 2-227 Cl Cl F CH.sub.3 O NH.sub.2 [00305] 2-228 Cl Cl F CH.sub.3 S NH.sub.2 [00306] 2-229 Cl Cl F CH.sub.3 O NH.sub.2 [00307] 2-230 Cl Cl F CH.sub.3 S NH.sub.2 [00308] 2-231 Cl Cl F CH.sub.3 O NH.sub.2 [00309] 2-232 Cl Cl F CH.sub.3 S NH.sub.2 [00310] 2-233 Cl Cl F CH.sub.3 O NH.sub.2 [00311] 2-234 Cl Cl F CH.sub.3 S NH.sub.2 [00312] 2-235 Cl Cl F CH.sub.3 O NH.sub.2 [00313] 2-236 Cl Cl F CH.sub.3 S NH.sub.2 [00314] 2-237 Cl Cl F CH.sub.3 O NH.sub.2 [00315] 2-238 Cl Cl F CH.sub.3 S NH.sub.2 [00316] 2-239 Cl Cl F CH.sub.3 O NH.sub.2 [00317] 2-240 Cl Cl F CH.sub.3 S NH.sub.2 [00318] 2-241 Cl Cl F CH.sub.3 O NH.sub.2 [00319] 2-242 Cl Cl F CH.sub.3 S NH.sub.2 [00320] 2-243 Cl Cl F CH.sub.3 O NH.sub.2 [00321] 2-244 Cl Cl F CH.sub.3 S NH.sub.2 [00322] 2-245 Cl Cl F CH.sub.3 O NH.sub.2 [00323] 2-246 Cl Cl F CH.sub.3 S NH.sub.2 [00324] 2-247 Cl Cl F CH.sub.3 O NH.sub.2 [00325] 2-248 Cl Cl F CH.sub.3 S NH.sub.2 [00326] 2-249 Cl Cl F CH.sub.3 O NH.sub.2 [00327] 2-250 Cl Cl F CH.sub.3 S NH.sub.2 [00328] 2-251 Cl Cl F CH.sub.3 O NH.sub.2 [00329] 2-252 Cl Cl F CH.sub.3 S NH.sub.2 [00330] 2-253 Cl Cl F CH.sub.3 O NH.sub.2 [00331] 2-254 Cl Cl F CH.sub.3 S NH.sub.2 [00332] 2-255 Cl Cl F CH.sub.3 O NH.sub.2 [00333] 2-256 Cl Cl F CH.sub.3 S NH.sub.2 [00334] 2-257 Cl Cl F CH.sub.3 O NH.sub.2 [00335] 2-258 Cl Cl F CH.sub.3 S NH.sub.2 [00336] 2-259 Cl Cl F CH.sub.3 O NH.sub.2 [00337] 2-260 Cl Cl F CH.sub.3 S NH.sub.2 [00338] 2-261 Cl Cl F CH.sub.3 O NH.sub.2 [00339] 2-262 Cl Cl F CH.sub.3 S NH.sub.2 [00340] 2-263 Cl Cl F CH.sub.3 O NH.sub.2 [00341] 2-264 Cl Cl F CH.sub.3 O NH.sub.2 [00342] 2-265 Cl Cl F CH.sub.3 O NH.sub.2 [00343] 2-266 Cl Cl F CH.sub.3 S NH.sub.2 [00344] 2-267 Cl Cl F CH.sub.3 O NH.sub.2 [00345] 2-268 Cl Cl F CH.sub.3 O NH.sub.2 [00346] 2-269 Cl Cl F CH.sub.3 O NH.sub.2 [00347] 2-270 Cl Cl CH.sub.3 CH.sub.3 O NH.sub.2 [00348] 2-271 Cl Cl F CH.sub.3 O NH.sub.2 [00349] 2-272 Cl Cl F CH.sub.3 S NH.sub.2 [00350] 2-273 Cl Cl F CH.sub.3 O NH.sub.2 [00351] 2-274 Cl Cl F CH.sub.3 S NH.sub.2 [00352] 2-275 Cl Cl F CH.sub.3 O NH.sub.2 [00353] 2-276 Cl Cl F CH.sub.3 O NH.sub.2 [00354] 2-277 Cl Cl F CH.sub.3 O NH.sub.2 [00355] 2-278 Cl Cl F CH.sub.3 O NH.sub.2 [00356] 2-279 Cl Cl F CH.sub.3 O NH.sub.2 [00357] 2-280 Cl Cl F CH.sub.3 O NH.sub.2 [00358] 2-281 Cl Cl F CH.sub.3 O NH.sub.2 [00359] 2-282 Cl Cl F CH.sub.3 O NH.sub.2 [00360] 2-283 Cl Cl F CH.sub.3 O NH.sub.2 [00361] 2-284 Cl Cl F CH.sub.3 O NH.sub.2 [00362] 2-285 Cl Cl F CH.sub.3 O NH.sub.2 [00363] 2-286 Cl Cl F CH.sub.3 O NH.sub.2 [00364] 2-287 Cl Cl F CH.sub.3 O NH.sub.2 [00365] 2-288 Cl Cl F CH.sub.3 O NH.sub.2 [00366] 2-289 Cl Cl F CH.sub.3 O NH.sub.2 [00367] 2-290 Cl Cl F CH.sub.3 S NH.sub.2 [00368] 2-291 Cl Cl F CH.sub.3 O NH.sub.2 [00369] 2-292 Cl Cl F CH.sub.3 O NH.sub.2 [00370] 2-293 Cl Cl F CH.sub.3 O NH.sub.2 [00371] 2-294 Cl Cl F CH.sub.3 O NH.sub.2 [00372] 2-295 Cl Cl F CH.sub.3 O NH.sub.2 [00373] 2-296 Cl Cl F CH.sub.3 O NH.sub.2 [00374] 2-297 Cl Cl F CH.sub.3 O NH.sub.2 [00375] 2-298 Cl Cl F CH.sub.3 O NH.sub.2 [00376] 2-299 Cl Cl F CH.sub.3 O NH.sub.2 [00377] 2-300 Cl Cl F CH.sub.3 O NH.sub.2 [00378] 2-301 Cl Cl F CH.sub.3 S NH.sub.2 [00379] 2-302 Cl Cl F CH.sub.3 O NH.sub.2 [00380] 2-303 Cl Cl F CH.sub.3 S NH.sub.2 [00381] 2-304 Cl Cl F CH.sub.3 O NH.sub.2 [00382] 2-305 Cl Cl F CH.sub.3 S NH.sub.2 [00383] 2-306 Cl Cl F CH.sub.3 O NH.sub.2 [00384] 2-307 Cl Cl F CH.sub.3 S NH.sub.2 [00385] 2-308 Cl Cl F CH.sub.3 O NH.sub.2 [00386] 2-309 Cl Cl F CH.sub.3 S NH.sub.2 [00387] 2-310 Cl Cl F CH.sub.3 O NH.sub.2 [00388] 2-311 Cl Cl F CH.sub.3 S NH.sub.2 [00389] 2-312 Cl Cl F CH.sub.3 O NH.sub.2 [00390] 2-313 Cl Cl F CH.sub.3 S NH.sub.2 [00391] 2-314 Cl Cl F CH.sub.3 O NH.sub.2 [00392] 2-315 Cl Cl F CH.sub.3 S NH.sub.2 [00393] 2-316 Cl Cl F CH.sub.3 O NH.sub.2 [00394] 2-317 Cl Cl F CH.sub.3 S NH.sub.2 [00395] 2-318 Cl Cl F CH.sub.3 O NH.sub.2 [00396] 2-319 Cl Cl F CH.sub.3 S NH.sub.2 [00397] 2-320 Cl Cl F CH.sub.3 O NH.sub.2 [00398] 2-321 Cl Cl F CH.sub.3 S NH.sub.2 [00399] 2-322 Cl Cl F CH.sub.3 O NH.sub.2 [00400] 2-323 Cl Cl F CH.sub.3 S NH.sub.2 [00401] 2-324 Cl Cl F CH.sub.3 O NH.sub.2 [00402] 2-325 Cl Cl F CH.sub.3 S NH.sub.2 [00403] 2-326 Cl Cl F Et O NH.sub.2 [00404] 2-327 Cl Cl F CH.sub.3 O NH.sub.2 [00405] 2-328 Cl Cl F CH.sub.3 S NH.sub.2 [00406] 2-329 Cl Cl F CH.sub.3 O NH.sub.2 [00407] 2-330 Cl Cl F CH.sub.3 S NH.sub.2 [00408] 2-331 Cl Cl F CH.sub.3 O NH.sub.2 [00409] 2-332 Cl Cl F CH.sub.3 S NH.sub.2 [00410] 2-333 Cl Cl F CH.sub.3 O NH.sub.2 [00411] 2-334 Cl Cl F CH.sub.3 S NH.sub.2 [00412] 2-335 Cl Cl F CH.sub.3 O NH.sub.2 [00413] 2-336 Cl Cl F CH.sub.3 S NH.sub.2 [00414] 2-337 Cl Cl F CH.sub.3 O NH.sub.2 [00415] 2-338 Cl Cl F CH.sub.3 S NH.sub.2 [00416] 2-339 Cl Cl F CH.sub.3 S NH.sub.2 [00417] 2-340 Cl Cl F CH.sub.3 O NH.sub.2 [00418] 2-341 Cl Cl F CH.sub.3 O NH.sub.2 [00419] 2-342 Cl Cl F CH.sub.3 O NH.sub.2 [00420] 2-343 Cl Cl F CH.sub.3 S NH.sub.2 [00421] 2-344 Cl Cl F CH.sub.3 O NH.sub.2 [00422] 2-345 Cl Cl F CH.sub.3 S NH.sub.2 [00423] 2-346 Cl Cl F CH.sub.3 O NH.sub.2 [00424] 2-347 Cl Cl F CH.sub.3 S NH.sub.2 [00425] 2-348 Cl Cl F CH.sub.3 O NH.sub.2 [00426] 2-349 Cl Cl F CH.sub.3 O NH.sub.2 [00427] 2-350 Cl Cl F CH.sub.3 O NH.sub.2 [00428] 2-351 Cl Cl F CH.sub.3 O NH.sub.2 [00429] 2-352 Cl Cl F CH.sub.3 O NH.sub.2 [00430] 2-353 Cl Cl F CH.sub.3 O NH.sub.2 [00431] 2-354 Cl Cl F CH.sub.3 O NH.sub.2 [00432] 2-355 Cl Cl F CH.sub.3 O NH.sub.2 [00433] 2-356 Cl Cl F CH.sub.3 O NH.sub.2 [00434] 2-357 Cl Cl F CH.sub.3 S NH.sub.2 [00435] 2-358 Cl Cl F CH.sub.3 S NH.sub.2 [00436] 2-359 Cl Cl F CH.sub.3 O NH.sub.2 [00437] 2-360 Cl Cl F CH.sub.3 S NH.sub.2 [00438] 2-361 Cl Cl F CH.sub.3 O NH.sub.2 [00439] 2-362 Cl Cl F CH.sub.3 O NH.sub.2 [00440] 2-363 Cl Cl F CH.sub.3 S NH.sub.2 [00441] 2-364 Cl Cl F CH.sub.3 O NH.sub.2 [00442] 2-365 Cl Cl F CH.sub.3 S NH.sub.2 [00443] 2-366 Cl Cl F CH.sub.3 O NH.sub.2 [00444] 2-367 Cl Cl F CH.sub.3 O NH.sub.2 [00445] 2-368 Cl Cl F CH.sub.3 S NH.sub.2 [00446] 2-369 Cl Cl F CH.sub.3 O NH.sub.2 [00447] 2-370 Cl Cl F CH.sub.3 O NH.sub.2 [00448] 2-371 Cl Cl F CH.sub.3 O NH.sub.2 [00449] 2-372 Cl Cl F CH.sub.3 O NH.sub.2 [00450] 2-373 Cl Cl F CH.sub.3 S NH.sub.2 [00451] 2-374 Cl Cl F CH.sub.3 O NH.sub.2 [00452] 2-375 Cl Cl F CH.sub.3 O [00453] CH.sub.3 2-376 Cl Cl F CH.sub.3 S [00454] CH.sub.3 2-377 Cl Cl F CH.sub.3 O [00455] CH.sub.3 2-378 Cl Cl F CH.sub.3 O [00456] CH.sub.3 2-379 Cl Cl F CH.sub.3 O [00457] CH.sub.3 2-380 Cl Cl F CH.sub.3 O [00458] CH.sub.3 2-381 Cl Cl F CH.sub.3 O [00459] CH.sub.3 2-382 Cl Cl F [00460] O NH.sub.2 Et 2-383 Cl Cl F [00461] O NH.sub.2 Et 2-384 Cl Cl F Et O NH.sub.2 [00462] 2-385 Cl Cl F [00463] S NH.sub.2 CH.sub.3 2-386 Cl Cl CH.sub.3 CH.sub.3 O NH.sub.2 [00464] 2-387 Cl Cl F CH.sub.3 O [00465] CH.sub.3

TABLE-US-00003 TABLE 3 .sup.1HNMR data of compounds No. .sup.1HNMR 1-2 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.33 (s, 1H), 7.07 (s, 2H), 5.15 (q, J = 7.0 Hz, 1H), 1.50 (d, J = 7.0 Hz, 3H). 1-4 .sup.1H NMR (500 MHz, Chloroform-d) δ 7.63 − 7.61 (m, 2H), 7.45 − 7.38 (m, 3H), 6.13 (s, 1H), 5.18 (s, 2H) 1-26 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.96 (s, 1H), 6.99 (s, 2H), 5.06 (q, J = 7.0 Hz, 1H), 1.50 (d, J = 7.0 Hz, 3H) 1-27 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.82 (s, 2H), 4.18 (dd, J = 11.0, 2.0 Hz, 1H), 2.05 − 2.27 (m, 2H), 0.93 (t, J = 8.0 Hz, 3H). 1-71 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 12.42 (s, 1H), 8.21 (d, J = 2.5 Hz, 1H), 7.76 (t, J = 5.5 Hz, 1H), 7.21 − 7.11 (m, 2H), 5.15 (q, J = 7.0 Hz, 1H), 4.98 (d, J = 5.5 Hz, 2H), 1.50 (d, J = 7.0 Hz, 3H). 2-28 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.53 (s, 1H), 6.36 (s, 2H), 4.63 (q, J = 7.0 Hz, 1H), 3.72 (s, 3H), 2.08 (s, 3H), 1.50 (d, J = 7.0 Hz, 3H). 2-29 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.36 (s, 2H), 4.66 (q, J = 7.0 Hz, 1H), 3.72 (s, 3H), 2.08 (s, 3H), 1.51 (d, J = 7.0 Hz, 3H). 2-30 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.61 (s, 1H), 6.80 (s, 2H), 4.63 (q, J = 7.0 Hz, 1H), 3.72 (s, 3H), 1.51 (d, J = 7.0 Hz, 3H). 2-31 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.81 (s, 2H), 4.66 (q, J = 7.0 Hz, 1H), 3.72 (s, 3H), 1.52 (d, J = 7.0 Hz, 3H). 2-32 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.81 (s, 2H), 4.65 (q, J = 7.0 Hz, 1H), 3.72 (s, 3H), 2.53 (s, 3H), 1.51 (d, J = 7.0 Hz, 3H). 2-33 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.79 (s, 2H), 4.74 (dd, J = 10.0, 2.5 Hz, 1H), 2.31 (s, 3H), 1.84 (dtd, J = 8.0, 4.0, 2.0 Hz, 1H), 1.74 − 1.84 (m, 1H), 0.89 (t, J = 8.0 Hz, 3H). 2-34 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.04 (s, 2H), 5.00-5.03 (m, 1H), 3.66 (s, 3H), 1.84-1.94 (m, 2H), 0.96-1.0 (m, 3H). 2-35 .sup.1H NMR (500 MHz, Chloroform-d) δ 5.14 (s, 2H), 4.97 (d, J = 4.5 Hz, 1H), 3.75 (s, 3H), 2.31-2.37 (m, 1H), 1.09 (dd, J = 7.0, 2.0 Hz, 6H). 2-36 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.79 (s, 2H), 4.83 (d, J = 7.0 Hz, 1H), 2.31 (s, 3H), 2.27 (dt, J = 13.5, 7.0 Hz, 1H), 0.88 (dd, J = 25.0, 7.0 Hz, 6H). 2-37 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.32 (dd, J = 11.0, 1.0 Hz, 1H), 3.72 (s, 3H), 1.81 − 1.92 (m, 1H), 1.54 − 1.69 (m, 2H), 1.35 − 1.49 (m, 1H), 0.77 − 0.85 (m, 3H). 2-38 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.77 (s, 2H), 4.63 (d, J = 7.0 Hz, 1H), 3.72 (s, 3H), 0.79-0.86 (m, 1H), 0.37 − 0.49 (m, 2H), 0.28-0.33 (m, 2H). 2-39 .sup.1H NMR (500 MHz, Chloroform-d) δ 5.05 (q, J = 7.0 Hz, 1H), 4.44 (s, 2H), 3.85 (s, 3H). 2-40 .sup.1H NMR (500 MHz, Chloroform-d) δ 4.52 (dd, J = 11.0, 2.0 Hz, 1H), 4.44 (s, 2H), 3.85 (s, 3H), 2.77-2.87 (m, 1H), 2.65-2.73 (m, 1H). 2-41 .sup.1H NMR (500 MHz, Chloroform-d) δ 4.74 (t, J = 7.0 Hz, 1H), 4.44 (s, 2H), 4.35 (dd, J = 12.5, 7.0 Hz, 1H), 4.00 (dd, J = 12.5, 7.0 Hz, 1H), 3.85 (s, 3H). 2-42 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.58-4.61 (m, 1H), 3.78 − 3.86 (m, 1H), 3.72 (s, 3H), 3.63-3.69 (m, 1H), 2.24-2.29 (m, 1H), 2.07-2.13 (m, 1H). 2-43 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 5.16 − 5.25 (m, 1H), 5.11 (dd, J = 10.5, 5.0 Hz, 1H), 4.83 − 4.92 (m, 1H), 4.75 − 4.85 (m, 1H), 3.72 (s, 3H). 2-44 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 6.29 (d, J = 7.0 Hz, 1H), 5.16-5.25 (m, 1H), 3.72 (s, 3H). 2-45 .sup.1H NMR (500 MHz, Chloroform-d) δ 6.12-6.19 (m, 1H), 5.43 − 5.45 (m, 1H), 5.32-5.37 (m, 1H), 5.15-5.21 (m, 1H), 4.45 (s, 2H), 3.70 (s, 3H). 2-46 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 5.67 (d, J = 3.0 Hz, 1H), 3.68 (d, J = 3.0 Hz, 1H), 3.65 (s, 3H). 2-47 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.18 (s, 2H), 5.80 (s, 1H), 3.76 (s, 6H). 2-48 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 9.95 (d, J = 6.0 Hz, 1H), 6.80 (s, 2H), 5.38 (d, J = 6.0 Hz, 1H), 3.63 (s, 3H). 2-49 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.79 (s, 2H), 4.97 (t, J = 5.5 Hz, 1H), 4.35 (t, J = 7.0 Hz, 1H), 4.21-4.26 (m, 1H), 3.91-3.96 (m, 1H), 3.72 (s, 3H). 2-50 .sup.1H NMR (500 MHz, Chloroform-d) δ 7.27 (s, 1H), 4.45 (s, 2H), 3.71 (s, 3H). 2-51 .sup.1H NMR (500 MHz, Chloroform-d) δ 6.96 (s, 1H), 6.86 (d, J = 47.0 Hz, 1H), 4.45 (s, 2H), 3.74 (s, 3H). 2-52 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.83 (s, 2H), 6.76 (s, 1H), 3.66 (s, 3H). 2-53 .sup.1H NMR (500 MHz, Chloroform-d) δ 6.62 (s, 1H), 4.47 (s, 2H), 3.73 (s, 3H). 2-54 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.07 (s, 2H), 5.31-5.33 (m, 1H), 3.85 − 3.89 (m, 1H), 3.72 − 3.77 (m, 1H), 3.66 (s, 3H), 3.34 (s, 3H). 2-55 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.43 (t, J = 7.0 Hz, 1H), 4.02 (dd, J = 12.5, 7.0 Hz, 1H), 3.87 (dd, J = 12.5, 7.0 Hz, 1H), 3.19 (s, 3H), 2.31 (s, 3H). 2-56 .sup.1H NMR (500 MHz, Chloroform-d) δ 5.97 (s, 1H), 4.46 (s, 2H), 3.71 (s, 3H), 1.97 (s, 2H). 2-57 .sup.1H NMR (500 MHz, Chloroform-d) δ 5.80 (s, 1H), 4.44 (s, 2H), 3.71 (s, 3H), 2.23 (s, 3H). 2-58 .sup.1H NMR (500 MHz, Chloroform-d) δ 6.17 (s, 1H), 4.45 (s, 2H), 3.71 (s, 3H), 3.42 (s, 3H). 2-59 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.81 (s, 2H), 4.49 (t, J = 7.0 Hz, 1H), 3.72 (s, 3H), 3.14 (dd, J = 12.5,7.1 Hz, 1H), 2.62 (dd, J = 12.5, 7.0 Hz, 1H), 2.25 (s, 6H). 2-60 .sup.1H NMR (500 MHz, Chloroform-d) δ 4.91 (t, J = 7.0 Hz, 1H), 4.45 (s, 2H), 3.85 (s, 3H), 3.33-3.37 (m, 1H), 2.95-3.00 (m, 1H). 2-61 .sup.1H NMR (500 MHz, Chloroform-d) δ 5.76 (s, 1H), 4.45 (s, 2H), 3.75 (s, 3H). 2-62 .sup.1H NMR (500 MHz, Chloroform-d) δ 7.61 − 7.63 (m, 2H), 7.38 − 7.45 (m, 3H), 6.13 (s, 1H), 5.18 (s, 2H), 3.73 (s, 3H). 2-63 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.33 − 7.40 (m, 2H), 7.20 − 7.28 (m, 2H), 7.15 − 7.23 (m, 1H), 6.76 (s, 2H), 5.22 (t, J = 7.0 Hz, 1H), 3.72 (s, 3H), 3.31 − 2.98 (m, 2H). 2-64 .sup.1H NMR (500 MHz, Chloroform-d) δ 7.61 − 7.63 (m, 2H), 7.38 − 7.45 (m, 2H), 6.13 (s, 1H), 5.18 (s, 2H), 3.73 (s, 3H). 2-65 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.41 (dd, J = 7.5, 1.5 Hz, 1H), 7.17 (dd, J = 7.5, 1.5 Hz, 1H), 7.06 (t, J = 7.5 Hz, 1H), 6.82 (s, 2H), 6.22 (s, 1H), 3.66 (s, 3H). 2-67 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.27 (s, 1H), 6.82 (s, 2H), 6.14 (s, 1H), 3.66 (s, 3H). 2-68 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.50(d, J = 8.0 Hz, 1H), 7.23 (s, 2H), 5.81 (s, 1H), 3.67 (s, 3H). 2-69 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.04 (s, 2H), 5.15 (q, J = 7.0 Hz, 1H), 3.65 (s, 3H), 1.50 (d, J = 7.0 Hz, 3H). 2-70 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.99 (q, J = 7.0 Hz, 1H), 2.31 (s, 3H), 1.54 (d, J = 7.0 Hz, 3H). 2-71 .sup.1H NMR (500 MHz, Chloroform-d) δ 5.24 (q, J = 7.0 Hz, 1H), 5.15 (s, 2H), 4.19 − 4.25 (m, 2H), 1.64 (d, J = 7.5 Hz, 3H), 1.27 (t, J = 7.5 Hz, 3H). 2-72 .sup.1H NMR (500 MHz, Chloroform-d) δ 5.52 (q, J = 7.0 Hz, 1H), 5.19 (s, 2H), 2.84-2.92 (m, 2H), 1.60 (d, J = 7.0 Hz, 3H), 1.25 (t, J = 7.5 Hz, 3H). 2-73 .sup.1H NMR (500 MHz, Chloroform-d) δ 5.25 (q, J = 7.0 Hz, 1H), 5.14 (s, 2H), 4.09 − 4.15 (m, 2H), 1.55-1.68 (m, 5H), 0.92 (t, J = 7.5 Hz, 3H). 2-74 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.97 (q, J = 7.0 Hz, 1H), 3.42 (td, J = 12.5, 3.0 Hz, 1H), 2.90 (td, J = 12.5, 2.5 Hz, 1H), 1.71-1.86 (m, 1H), 1.54 (d, J = 7.0 Hz, 3H), 1.34-1.44 (m, 1H), 0.98 (t, J = 8.0 Hz, 3H). 2-75 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.03 (s, 2H), 5.03 (q, J = 7.0 Hz, 1H), 4.89-4.94 (m, 1H), 1.49 (d, J = 7.0 Hz, 3H), 1.19 (d, J = 6.5 Hz, 3H), 1.14(d, J = 6.5 Hz, 3H). 2-76 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 5.00 (q, J = 7.0 Hz, 1H), 3.36 (dq, J = 13.5, 7.0 Hz, 1H), 1.54 (d, J = 7.0 Hz, 3H), 1.30 (s, 6H). 2-77 .sup.1H NMR (500 MHz, Chloroform-d) δ 5.24 (q, J = 7.0 Hz, 1H), 5.15 (s, 2H), 4.12 − 4.20 (m, 2H), 1.59 − 1.64 (m, 5H), 1.31 − 1.38 (m, 2H), 0.89 − 0.93 (m, 3H). 2-78 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.99 (q, J = 7.0 Hz, 1H), 3.29 (td, J = 12.5, 3.5 Hz, 1H), 3.04 (td, J = 12.5, 2.5 Hz, 1H), 1.62 − 1.75 (m, 1H), 1.44 − 1.57 (m, 4H), 1.33-1.41 (m, 1H), 1.14 − 1.27 (m, 1H), 0.92 (t, J = 8.0 Hz, 3H). 2-79 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.67 (q, J = 7.0 Hz, 1H), 4.23 (dd, J = 12.5, 7.0 Hz, 1H), 3.12 (dd, J = 12.5, 7.0 Hz, 1H), 1.93-2.01 (m, 1H), 1.51 (d, J = 7.0 Hz, 3H), 0.88 (d, J = 7.0 Hz, 6H). 2-80 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 5.01 (q, J = 7.0 Hz, 1H), 3.56 (dd, J = 12.5, 7.0 Hz, 1H), 2.89 (dd, J = 12.5, 7.0 Hz, 1H), 1.73 (dp, J = 13.5, 7.0 Hz, 1H), 1.54 (d, J = 7.0 Hz, 3H), 0.92 (dd, J = 25,7.0 Hz, 6H). 2-81 .sup.1H NMR (500 MHz, Chloroform-d) δ 5.17-5.20 (m, 1H), 5.14 (s, 2H), 4.86-4.94 (m, 1H), 1.51-1.66(m, 5H), 1.18-1.28 (m, 3H), 0.83-0.95 (m, 3H) 2-82 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.79 (s, 2H), 5.00 (q, J = 7.0 Hz, 1H), 2.88-2.95 (m, 1H), 2.21-2.27 (m, 1H), 1.51 − 1.62 (m, 4H), 1.32 (d, J = 7.0 Hz, 3H), 0.88 (t, J = 8.0 Hz, 3H). 2-83 .sup.1H NMR (500 MHz, Chloroform-d) δ 5.14 (s, 2H), 5.09 (q, J = 7.0 Hz, 1H), 1.60 (d, J = 7.0 Hz, 3H), 1.46 (s, 9H). 2-84 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 5.01 (q, J = 7.0 Hz, 1H), 1.53 (d, J = 7.0 Hz, 3H), 1.32 (s, 9H). 2-85 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.67 (q, J = 7.0 Hz, 1H), 4.07 − 3.97 (m, 1H), 3.90 (td, J = 12.5, 3.0 Hz, 1H), 1.52 (d, J = 7.0 Hz, 3H), 1.32 − 1.13 (m, 6H), 0.90 (t, J = 7.0 Hz, 3H). 2-86 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.97 (q, J = 7.0 Hz, 1H), 3.41 (td, J = 12.5, 3.5 Hz, 1H), 2.89 (td, J = 12.5, 2.5 Hz, 1H), 1.69-1.75 (m, 1H), 1.54 (d, J = 6.5 Hz, 3H), 1.10 − 1.38 (m, 4H), 0.84 − 0.92 (m, 2H), 0.88 (s, 2H). 2-87 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.67 (q, J = 7.0 Hz, 1H), 4.15 (dd, J = 12.5, 7.0 Hz, 1H), 3.67 (dd, J = 12.5, 7.0 Hz, 1H), 1.72 − 1.85 (m, J = 7.0 Hz, 1H), 1.51 (d, J = 7.0 Hz, 3H), 1.23 − 1.35 (m, 1H), 1.07 − 1.20 (m, 1H), 0.83 − 0.92 (m, 6H). 2-88 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 5.00 (q, J = 7. Hz, 1H), 3.28 (dd, J = 12.5, 7.0 Hz, 1H), 2.74 (dd, J = 12.5, 7.0 Hz, 1H), 1.61 − 1.74 (m, 1H), 1.54 (d, J = 7.0 Hz, 3H), 1.28 − 1.41 (m, 1H), 1.08-1.14 (m, 1H), 0.91 (d, J = 7.0 Hz, 3H), 0.84 (t, J = 8.0 Hz, 3H). 2-89 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.67 (q, J = 7.0 Hz, 1H), 4.43-4.47 (m, 1H), 3.44-3.50 (m, 1H), 1.77-1.85 (m, 1H), 1.51 (d, J = 7.0 Hz, 3H), 1.42-1.47 (m, 1H), 1.24-1.31 (3, 1H), 0.97 (d,J = 7.0 Hz, 6H). 2-90 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80(s, 2H), 4.99 (q, J = 6.9 Hz, 1H), 3.51 (td, J = 12.2, 4.2 Hz, 1H), 2.89 (td, J = 12.3, 3.1 Hz, 1H), 1.68 − 1.58 (m, 1H), 1.62 − 1.44 (m, 5H), 0.85 (dd, J = 25.0, 6.7 Hz, 6H). 2-91 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.81 (s, 2H), 4.68 (q, J = 7.0 Hz, 1H), 3.50 − 3.61 (m, 2H), 1.53 (d, J = 7.0 Hz, 3H), 1.05 (s, 9H). 2-92 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.99-5.03 (m, 1H), 3.70 (d, J = 12.5 Hz, 1H), 2.84 (d, J = 12.5 Hz, 1H), 1.54 (d, J = 7.0 Hz, 3H), 0.86 (s, 9H). 2-93 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80(s, 2H), 4.68 (q, J = 7.0 Hz, 2H), 1.52(d, J = 7.0 Hz, 3H), 1.34 − 1.48 (m, 1H), 1.13 − 1.25 (m, 5H), 1.03 − 1.16 (m, 1H), 0.81 (t, J = 8.0 Hz, 3H). 2-94 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.79 (s, 2H), 5.02 (q, J = 7.0 Hz, 1H), 3.27-3.34 (m, 1H), 2.15-2.22 (m, 1H), 1.45 − 1.57 (m, 4H), 1.29 (d, J = 7.0 Hz, 3H), 1.02 − 1.23 (m, 2H), 0.79 (t, J = 8.0 Hz, 3H). 2-95 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.66-4.75 (m, 2H), 1.92 − 2.05 (m, J = 7.0 Hz, 1H), 1.52 (d, J = 7.0 Hz, 3H), 1.17 (d, J = 7.0 Hz, 3H), 0.79 (d, J = 7.0 Hz, 6H). 2-96 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 5.00 (q, J = 7.0 Hz, 1H), 3.08-3.13 (m, 1H), 1.73-1.80 (m, 1H), 1.54(d, J = 7.0 Hz, 3H), 1.34 (d, J = 7.0 Hz, 3H), 0.84-0.90(m, 6H). 2-97 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.64 − 4.72 (m, 1H), 3.07-3.12 (m, 1H), 1.52 (d, J = 7.0 Hz, 3H), 1.25-1.32 (m, 4H), 0.83 (t, J = 8.0 Hz, 6H). 2-98 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.99-5.03 (m, 1H), 2.89-2.94 (m, 1H), 1.94 − 2.08 (m, 2H), 1.54 (d, J = 7.0 Hz, 3H), 1.37 − 1.45 (m, 2H), 0.82 (t, J = 8.0 Hz, 6H). 2-99 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80(s, 2H), 4.68 (q, J = 7.0 Hz, 1H), 1.56-1.63 (m,1H), 1.52(d, J = 7.0 Hz, 3H), 1.34 − 1.45 (m, 7H), 0.84 (t, J = 8.0 Hz, 3H). 2-100 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.99-5.03 (m, 1H), 2.20-2.27 (m, 1H), 1.44 − 1.56 (m, 4H), 1.35 (s, 3H), 1.30 (s, 3H), 0.82 (t, J = 8.0 Hz, 3H). 2-101 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.81 (s, 2H), 4.67 (q, J = 7.0 Hz, 1H), 3.89 − 4.02 (m, 2H), 1.52 (d, J = 6.5 Hz, 3H), 1.11 − 1.31 (m, 8H), 0.85-0.89 (m, 3H). 2-102 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 5.00 (q, J = 7.0 Hz, 1H), 3.41-3.47( m, 1H), 2.86-2.92 (m, 1H), 1.54 − 1.65 (m, 1H), 1.54 (d, J = 7.0 Hz, 3H), 1.09 − 1.41 (m, 6H), 1.00 − 1.12(m, 1H),0.87 (t, J = 8.0 Hz, 3H). 2-103 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.67 (q, J = 7.0 Hz, 1H), 4.23 (dd, J = 12.5, 7.0 Hz, 1H), 3.57 (dd, J = 12.5, 7.0 Hz, 1H), 1.67 − 1.81 (m, 1H), 1.40 − 1.54(m, 4H), 1.25-1.30(m, 1H), 1.14-1.22 (m, 1H), 1.00-1.10 (m, 1H), 0.79 − 0.89 (m, 6H). 2-104 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.99 (q, J = 7.0 Hz, 1H), 3.15-3.19 (m, 1H), 2.82 − 2.90 (m, 1H), 1.63-1.70(m, 1H), 1.49 − 1.60 (m, 4H), 1.35-1.40 (m, 1H), 1.12 − 1.26 (m, 2H), 0.79 − 0.91 (m, 6H). 2-105 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.81 (s, 2H), 4.67 (q, J = 7.0 Hz, 1H), 4.10 − 4.20 (m, 1H), 3.84 − 3.93 (m, 1H), 1.52 (d, J = 7.0 Hz, 3H), 1.23 − 1.39 (m, 4H), 1.09 − 1.20 (m, 1H), 0.83 − 0.92 (m, 6H). 2-106 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.99 (q, J = 7.0 Hz, 1H), 3.50-3.56 (m, 1H), 2.86-2.92 (m, 1H), 1.85-1.92 (m, 1H), 1.54 (d, J = 7.0 Hz, 3H), 1.19 − 1.46 (m, 3H), 1.08 − 1.20 (m, 1H), 0.81 +31 0.88(m, 6H). 2-107 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.68 (q, J = 7.0 Hz, 1H), 4.42-4.48 (m, 1H), 3.49-3.45 (m, 1H), 1.53 (dd, J = 16.5, 7.0 Hz, 4H), 1.39 − 1.51 (m, 1H), 1.26-1.33 (m, 1H), 1.16-1.23 (m, 1H), 1.03 − 1.16 (m, 1H), 0.92 (d, J = 7.0 Hz, 3H), 0.90 (d, J = 7.0 Hz, 3H). 2-108 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.99 (q, J = 7.0 Hz, 1H), 3.25-3.31 (m, 1H), 2.99-3.04 (m, 1H), 1.72 − 1.85 (m, 1H),1.48 − 1.56 (m, 4H), 1.37-1.46 (m, 1H), 1.14 − 1.31 (m, 2H),0.88 − 0.9 4 (m, 6H). 2-113 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.81 (s, 2H), 4.64 − 4.78 (m, 1H), 1.52 (d, J = 7.0 Hz, 3H), 1.33 − 1.47 (m, 4H), 1.05 − 1.26 (m, 6H), 0.88 (t, J = 8.0 Hz, 3H). 2-114 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.79 (s, 2H), 4.99-5.03 (m, 1H), 3.00 − 3.10 (m, 1H), 2.13 − 2.22(m, 1H), 1.42 − 1.57 (m, 6H), 1.31 (d, J = 7.0 Hz, 3H), 1.11 − 1.30 (m, 2H), 0.88 (t, J = 7.5 Hz, 3H). 2-121 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.81 (s, 2H), 4.67 (q, J = 7.0 Hz, 1H), 3.98-4.03 (m, 1H), 3.95 − 3.85 (m, 1H), 1.52 (d, J = 7.0 Hz, 3H), 1.13 − 1.32 (m, 8H), 0.83 − 0.91 (m, 2H), 0.87(t, J = 7.5 Hz, 3H). 2-122 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.99 (q, J = 7 .0 Hz, 1H), 3.23 − 3.33 (m, 1H), 2.96-3.06 (m, 1H), 1.48 − 1.63 (m, 6H), 1.09 − 1.30 (m, 7H), 0.85-.88 (m, 3H). 2-155 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.81 (s, 2H), 4.67 (q, J = 7.0 Hz, 1H), 3.90 − 4.02 (m, 2H), 1.52 (d, J = 7.0 Hz, 3H), 1.31 − 1.43 (m, 1H), 1.16 − 1.31 (m, 10H), 1.17 (s, 1H), 0.87 (t, J = 7.5 Hz, 3H). 2-156 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 5.00 (q, J = 7.0 Hz, 1H), 3.26 (dd, J = 12.5, 7.0 Hz, 1H), 2.78 (dd, J = 12.5,7.0 Hz, 1H), 1.36-1.71 (m, 8H), 1.09 − 1.25 (m, 2H), 0.99-1.12 (m, 2H), 0.82-0.90 (m, 6H). 2-157 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.68 (q, J = 7.0 Hz, 1H), 4.14 (dd, J = 12.5, 7.0 Hz, 1H), 3.82 (dd, J = 12.5, 7.0 Hz, 1H), 1.66-1.68 (m, 1H), 1.49 − 1.62 (m, 4H), 1.36 − 1.52 (m, 2H), 1.03 − 1.29(m, 4H), 0.94-0.99 (m, 4H), 0.88 (t, J = 8.0 Hz, 3H). 2-158 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 5.00 (q, J = 7.0 Hz, 1H), 3.26 (dd, J = 12.5, 7.0 Hz, 1H), 2.78 (dd, J = 12.5, 7.0 Hz, 1H), 1.71-1.36(m, 8H), 1.25 − 1.09 (m, 2H), 1.12 − 0.99 (m, 2H), 0.90-0.80 (m, 6H). 2-159 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.81 (s, 2H), 4.67 (q, J = 7.0 Hz, 1H), 3.89 − 4.02 (m, 2H), 1.52 (dd, J = 7.0, 3.0 Hz, 4H), 1.35 − 1.49 (m, 1H), 1.00 − 1.34 (m, 7H), 0.93 (d, J = 7.0 Hz, 3H), 0.89 (d, J = 7.0 Hz, 3H). 2-160 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.99 (q, J = 7.0 Hz, 1H), 3.23 − 3.45 (m, 1H), 2.95 − 3.06 (m, 1H), 1.47 − 1.63 (m, 7H), 1.34 − 1.50(m, 1H), 1.19 − 1.31 (m, 1H), 1.15-1.18 (m, 2H), 1.00 − 1.15 (m, 1H), 0.91 (dd, J = 25.0, 7.0 Hz, 6H). 2-163 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.81 (s, 2H), 4.68 (qd, J = 7.0, 2.0 Hz, 2H), 1.52 (d, J = 7.0 Hz, 3H), 1.46 − 1.35 (m, 1H), 1.28 (s, 1H), 1.20 − 1.29 (m, 1H), 1.12 − 1.24 (m, 9H), 1.00 − 1.10 (m, 1H), 0.86-0.88(m, 3H). 2-164 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 5.00 (q, J = 7.0 Hz, 1H), 3.09 − 3.20 (m, 1H), 1.68 − 1.79 (m, 1H), 1.54 (d, J = 6.5 Hz, 3H), 1.32 − 1.45 (m, 2H), 1.29 (d, J = 7.0 Hz, 3H), 1.16-1.19(m, 6H), 1.13 (s, 1H), 0.86-0.88 (m, 3H). 2-175 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.81 (s, 2H), 4.67 (q, J = 7.0 Hz, 1H), 3.86 − 4.04 (m, 2H), 1.52 (d, J = 7.0 Hz, 3H), 1.12 − 1.31 (m, 14H),0.86-0.89(m, 3H). 2-176 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.79 (s, 2H), 4.99 (q, J = 7.0 Hz, 1H), 3.24 − 3.33 (m, 1H), 2.96- 3.06 (m, 1H), 1.47 − 1.62 (m, 5H), 1.14 − 1.31 (m, 11H), 1.07 − 1.17 (m, 1H), 0.85-0.89 (m, 3H). 2-195 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.67 (q, J = 7.0 Hz, 1H), 3.89 − 4.01 (m, 2H), 1.52 (d, J = 7.0 Hz, 3H), 1.08 − 1.33 (m, 16H), 0.84-0.90 (m, 3H). 2-196 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.99 (q, J = 7.0 Hz, 1H), 3.23 − 3.33 (m, 1H), 2.96- 3.06 (m, 1H), 1.49 − 1.62 (m, 5H), 1.11 − 1.26 (m, 14H), 0.82 − 0.93 (m, 3H). 2-215 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.81 (s, 2H), 4.67 (q, J = 7.0 Hz, 1H), 3.91-4.01 (m, 2H), 1.52 (d, J = 7.0 Hz, 3H), 1.21 − 1.31 (m, 2H), 1.12 − 1.24 (m, 16H), 0.83 − 0.91 (m, 3H) 2-216 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.99 (q, J = 7.0 Hz, 1H), 3.23 − 3.33 (m, 1H), 2.96-3.06 (m, 1H), 1.48 − 1.62 (m, 5H), 1.11 − 1.27 (m, 16H), 0.82-0.92 (m, 3H). 2-235 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.81 (s, 2H), 4.67 (q, J = 7.0 Hz, 1H), 4.00-4.05 (m, 1H), 3.83- 3.92 (m, 1H), 1.52 (d, J = 7.0 Hz, 3H), 109 − 1.32 (m, 20H), 0.82 − 0.92 (m, 3H). 2-236 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.99 (q, J = 7.0 Hz, 1H), 3.23 − 3.33 (m, 1H), 2.96 − 3.06 (m, 1H), 1.48 − 1.26 (m, 15H), 0.81 − 0.91 (m, 11H). 2-263 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.77 (s, 2H), 4.62 (q, J = 7.0 Hz, 1H), 3.32 (p, J = 7.0 Hz, 1H), 1.50 (d, J = 7.0 Hz, 3H), 0.44-0.48 (m, 2H), 0.23 − 0.35 (m, 2H). 2-264 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.68 (q, J = 7.0 Hz, 1H), 4.49 (p, J = 7.0 Hz, 1H), 2.09 − 2.20 (m, 2H), 1.78 − 1.92 (m, 3H), 1.63 − 1.76 (m, 1H), 1.52 (d, J = 7.0 Hz, 3H). 2-265 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.87 (p, J = 7.0 Hz, 1H), 4.68 (q, J = 7.0 Hz, 1H), 1.73-1.80 (m, 2H), 1.58-1.67 (m, 2H), 1.42 − 1.56 (m, 6H), 1.40-1.45 (m, 1H). 2-266 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.76 (s, 2H), 4.96 (s, 1H), 2.95 (s, 1H), 1.49 − 1.70 (m, 4H), 1.52 (s, 4H), 1.32-1.38 (m, 3H), 1.04-1.09 (m, 2H). 2-267 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 5.40 (d, J = 12.5 Hz, 1H), 4.89 (d, J = 12.5 Hz, 1H), 4.67 (q, J = 7.0 Hz, 1H), 1.53 (d, J = 7.0 Hz, 3H). 2-268 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.32 (d, J = 12.5 Hz, 1H), 6.80 (s, 2H), 6.29 (d, J = 12.5 Hz, 1H), 4.66 (q, J = 7.0 Hz, 1H), 1.56 (d, J = 7.0 Hz, 3H). 2-270 .sup.1H NMR (500 MHz, Ch1oroform-d) δ 4.49-4.58 (m, 2H), 4.45 (s, 2H), 3.72 − 3.62 (m, 1H), 3.60 − 3.50 (m, 2H), 3.37 (s, 3H), 2.51 (s, 3H), 1.68 (d, J = 7.0 Hz, 3H). 2-271 .sup.1H NMR (500 MHz, Ch1oroform-d) δ 4.67 (q, J = 6.5 Hz, 1H), 4.45 (s, 2H), 4.20 − 4.09 (m, 2H), 3.38 − 3.12 (m, 3H), 3.04 − 2.95 (m, 1H), 1.61 (d, J = 6.5 Hz, 3H), 1.59 − 1.15 (m, 4H), 1.03 (t, J = 7.5 Hz, 3H). 2-272 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.79 (s, 2H), 4.99 (q, J = 7.0 Hz, 1H), 3.37 (td, J = 12.5, 3.0 Hz, 1H), 3.30 (td, J = 12.0, 1.5 Hz, 1H), 3.21 (dt, J = 12.5, 3.0 Hz, 1H), 3.18 (s, 3H), 2.98 (td, J = 12.5, 3.5 Hz, 1H), 1.64 − 1.74 (m, 1H), 1.60 (tt, J = 12.0, 3.5 Hz, 1H), 1.54 (d, J = 7.0 Hz, 3H). 2-273 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.81 (s, 2H), 5.94-6.02 (m, 1H), 5.28 − 5.37 (m, 1H), 5.20 − 5.31 (m, 1H), 4.55 − 4.70 (m, 3H), 1.53 (d, J = 7.0 Hz, 3H). 2-274 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.96 (q, J = 7.0 Hz, 1H), 4.14 (dd, J = 12.5, 3.0 Hz, 1H), 3.53 (dd, J = 12.5, 3.0 Hz, 1H), 3.09 (t, J = 3.0 Hz, 1H), 1.61 (d, J = 7.0 Hz, 3H). 2-275 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.71 (dd, J = 12.5, 3.0 Hz, 1H), 4.59 − 4.70 (m, 2H), 3.55 (t, J = 3.0 Hz, 1H), 1.52 (d, J = 7.0 Hz, 3H). 2-276 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.50 − 4.83m, 3H), 4.25 − 4.48 (m, 2H), 1.50 (d, J = 7.0 Hz, 3H). 2-277 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.83 (dt, J = 12.5, 1.5 Hz, 1H), 4.70 (q, J = 7.0 Hz, 1H), 3.78 − 3.89 (m, 2H), 3.46-3.51(m, 1H), 1.52 (d, J = 7.0 Hz, 3H). 2-278 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.68 (q, J = 7.0 Hz, 1H), 4.54 (dt, J = 12.5, 2.0 Hz, 1H), 4.39-4.44 (m, 1H), 3.61 (dt, J = 12.5, 2.0 Hz, 1H), 3.29-3.34 (m, 1H), 1.48 (d, J = 7.0 Hz, 3H). 2-279 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 5.86 (t, J = 7.0 Hz, 1H), 4.68 − 4.78 (m, 1H), 4.62 − 4.72 (m, 1H), 3.74-3.87(m, 1H), 1.52 (d, J = 7.0 Hz, 3H). 2-280 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.06 (s, 2H), 5.13-5.14 (m, 1H), 4.15-4.17 (m, 2H), 2.12-2.26 (m, 2H), 1.74-1.77 (m, 2H), 1.43-1.52 (m, 3H). 2-281 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 5.17-5.25 (m, 1H), 4.66 (q, J = 7.0 Hz, 1H), 4.03-4.09 (m, 1H), 1.53 (d, J = 7.0 Hz, 3H). 2-282 .sup.1H NMR (500 MHz, Chloroform-d) δ 4.77-5.00 (m, 2H), 4.59 (q, J = 7.0 Hz, 1H), 4.45 (s, 2H), 1.69 (d, J = 7.0 Hz, 3H). 2-283 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.81 (s, 2H), 4.67 (q, J = 7.0 Hz, 1H), 4.37-4.42 (m, 1H), 4.02-4.08 (m, 1H), 2.75 (s, 6H), 2.59-2.62 (m, 1H), 1.79 − 1.89 (m, 1H), 1.52 (d, J = 7.0 Hz, 3H). 2-284 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.66 (q, J = 7.0 Hz, 1H), 4.45-4.50 (m, 1H), 3.46-3.51 (m, 1H), 2.80 (s, 2H), 2.60-2.74 (m, 2H), 1.52 (d, J = 7.0 Hz, 3H). 2-285 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.81 (s, 2H), 6.24-6.28 (m, 1H), 6.01-6.07 (m, 1H), 4.61 − 4.72 (m, 3H), 1.53 (d, J = 7.0 Hz, 3H). 2-286 .sup.1H NMR (500 MHz, Chloroform-d) δ 6.07 (d, J = 12.5 Hz, 1H), 4.57 (q, J = 7.0 Hz, 1H), 4.43 (s, 2H), 4.25 (d, J = 12.5 Hz, 1H), 1.67 (d, J = 7.0 Hz, 3H). 2-287 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.00 (s, 2H), 5.11 (q, J = 7.0 Hz, 1H), 4.31-4.27 (m, 1H), 4.20-4.15 (m, 1H), 4.08-4.00 (m, 2H), 1.75 (s, 3H), 1.66 (s, 3H), 1.48 (d, J = 7.0 Hz, 3H). 2-288 .sup.1H NMR (500 MHz, Chloroform-d) δ 5.90-5.98 (m, 1H), 5.13-5.26 (m, 1H), 5.22 − 5.11 (m, 1H), 4.94 − 4.86 (m, 1H), 4.68 − 4.59 (m, 2H), 4.45 (s, 2H), 1.69 (d, J = 7.0 Hz, 3H), 1.62 (s, 3H), 1.57 (s, 3H). 2-289 .sup.1H NMR (500 MHz, Chloroform-d) δ 5.32 (d, J = 12.5 Hz, 1H), 5.03 (d, J = 12.5 Hz, 1H), 4.70 (q, J = 6.5 Hz, 1H), 4.47 (s, 2H), 2.95 (s, 3H), 2.84 (s, 3H), 1.61 (d, J = 6.5 Hz, 3H). 2-290 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.82(s, 2H), 5.13 (q, J = 7.0 Hz, 1H), 4.26 (d, J = 12.5 Hz, 1H), 3.73 (d, J = 12.5 Hz, 1H), 3.67 (s, 3H), 1.50 (d, J = 7.0 Hz, 3H). 2-291 .sup.1H NMR (500 MHz, Ch1oroform-d) δ 6.00 (dd, J = 10.0, 1.5 Hz, 1H), 4.59 (q, J = 6.5 Hz, 1H), 4.45 (s, 2H), 3.27 (s, 3H), 1.77 − 1.68 (m, 4H), 1.23 − 0.87 (m, 4H). 2-292 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.79 (s, 2H), 4.73 (q, J = 7.0 Hz, 1H), 2.47 (s, 3H), 2.41 (s, 3H), 1.50 (d, J = 7.0 Hz, 3H). 2-294 .sup.1H NMR (500 MHz, Chloroform-d) δ 5.04 (d, J = 12.5 Hz, 1H), 4.89 (d, J = 12.5 Hz, 1H), 4.60 (q, J = 7.0 Hz, 1H), 4.45 (s, 2H), 4.23-4.30(m, 2H), 1.69 (d, J = 7.0 Hz, 3H), 1.22(t, J = 8.0 Hz, 3H). 2-295 .sup.1H NMR (500 MHz, Ch1oroform-d) δ 5.32 (q, J = 7.0 Hz, 1H), 4.62 (q, J = 7.0 Hz, 1H), 4.45 (s, 2H), 3.85 (s, 3H), 1.73 (d, J = 7.0 Hz, 3H), 1.59 (d, J = 7.0 Hz, 3H). 2-296 .sup.1H NMR (500 MHz, Ch1oroform-d) δ 7.82 (q, J = 6.5 Hz, 1H), 4.57 (q, J = 6.5 Hz, 1H), 4.45 (s, 2H), 4.01 (s, 3H), 1.69 − 1.52 (m, 6H). 2-297 .sup.1H NMR (500 MHz, Chloroform-d) δ 6.29 (t, J = 7.0 Hz, 1H), 4.57 (q, J = 7.0 Hz, 1H), 4.45 (s, 2H), 3.93-3.97 (m, 1H), 3.81-3.85 (m, 1H), 2.09 − 1.89 (m, 2H), 1.65-1.72 (m, 4H), 1.53-1.59 (m, 1H). 2-298 .sup.1H NMR (500 MHz, Ch1oroform-d) δ 5.28 (q, J = 7.0 Hz, 1H), 5.15 (s, 2H), 4.27 − 4.07 (m, 3H), 3.91 − 3.73 (m, 2H), 2.04 − 1.82 (m, 3H), 1.66 (d, J = 7.0 Hz, 3H), 1.59-1.54 (m, 1H). 2-299 .sup.1H NMR (500 MHz, Chloroform-d) δ 7.47 − 7.39 (m, 1H), 7.41 − 7.33 (m, 2H), 7.04 − 6.98 (m, 2H), 4.60 (q, J = 7.0 Hz, 1H), 4.42 (s, 2H), 1.76 (d, J = 7.0 Hz, 3H). 2-300 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.34-7.27 (m, 5H), 7.05 (s, 2H), 5.20-5.17 (m, 3H), 1.53 (d, J = 7.0 Hz, 3H). 2-301 .sup.1H NMR (500 MHz, Chloroform-d) δ 7.25 − 7.34 (m, 5H), 5.59 (q, J = 7.0 Hz, 1H), 5.21 (s, 2H), 4.15 (s, 2H), 1.65 (d, J = 7.0 Hz, 3H). 2-302 .sup.1H NMR (500 MHz, Chloroform-d) δ 7.31 − 7.17 (m, 4H), 5.77-5.79 (m, 1H), 4.68-4.71 (m, 1H), 4.55 (q, J = 7.0 Hz, 1H), 4.42 (s, 2H), 2.25 (s, 3H), 1.67 (d, J = 7.0 Hz, 3H). 2-303 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.17-7.20 (m, 1H), 7.10 − 7.19 (m, 2H), 7.02-7.06 (m, 1H), 6.76 (s, 2H), 4.92 (q, J = 7.0 Hz, 1H), 4.49 (dt, J = 12.0, 1.0 Hz, 1H), 4.30 − 4.40 (m, 1H), 2.23 (d, J = 1.5 Hz, 3H), 1.31 (d, J = 7.0 Hz, 3H). 2-304 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.38 (t, J = 7.5 Hz, 1H), 7.31-7.33 (m, 2H), 7.02-7.04 (m, 1H), 6.78 (s, 2H), 5.04-5.16 (m, 2H), 4.65 (q, J = 7.0 Hz, 1H), 2.22 (d, J = 2.0 Hz, 1H), 2.22 (s, 2H), 1.51 (d, J = 7.0 Hz, 3H). 2-305 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.25 − 7.34 (m, 2H), 7.22 − 7.29 (m, 1H), 6.93 − 6.99 (m, 1H), 6.77 (s, 2H), 4.99 (q, J = 7.0 Hz, 1H), 4.41 − 4.51 (m, 1H), 4.10 − 4.17 (m, 1H), 2.22 (d, J = 2.0 Hz, 1H), 2.22 (s, 2H), 1.53 (d, J = 7.0 Hz, 3H). 2-306 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.39 − 7.46 (m, 2H), 7.17 − 7.23(m, 2H), 6.78 (s, 2H), 5.10 (dt, J = 12.5, 1.0 Hz, 1H), 5.04 (d, J = 12.5 Hz, 1H), 4.65 (q, J = 7.0 Hz, 1H), 2.21 (d, J = 2.0 Hz, 1H), 2.21 (s, 2H), 1.51 (d, J = 7.0 Hz, 3H). 2-307 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.31 (dt, J = 7.5, 1.0 Hz, 2H), 7.09 (dd, J = 7.5, 1.5 Hz, 2H), 6.77 (s, 2H), 4.99 (q, J = 7.0 Hz, 1H), 4.47 (dt, J = 12.5, 1.0 Hz, 1H), 4.10 (dt, J = 12.5, 1.0 Hz, 1H),2.21 (d, J = 2.0 Hz, 1H), 2.21 (s, 2H), 1.54 (d, J = 7.0 Hz, 3H). 2-308 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.39 − 7.46 (m, 1H), 7.28 − 7.40 (m, 2H), 7.14-7.48 (m, 1H), 6.78 (s, 2H), 5.43 (dd, J = 12.5, 1.0 Hz, 1H), 5.07 (d, J = 12.5 Hz, 1H), 4.66 (q, J = 7.0 Hz, 1H), 1.52 (d, J = 7.0 Hz, 3H). 2-309 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.23-7.31 (m, 3H), 7.07 (td, J = 7.5, 2.0 Hz, 1H), 6.77 (s, 2H), 4.99 (q, J = 7.0 Hz, 1H), 4.52 (d, J = 12.5 Hz, 1H), 4.35 (dd, J = 12.5,1.0 Hz, 1H), 1.54 (d, J = 7.0 Hz, 3H). 2-310 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.37-7.41 (m, 1H), 7.28-7.30 (m, 1H), 7.22-7.24 (m, 1H), 7.00-7.04 (m, 1H), 6.77 (s, 2H), 5.40 (dt, J = 12.5, 1.0 Hz, 1H), 4.87 (d, J = 12.5 Hz, 1H), 4.64 (q, J = 7.0 Hz, 1H), 1.50 (d, J = 7.0 Hz, 3H). 2-311 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.33 (td, J = 7.5, 5.5 Hz, 1H), 7.21 (dq, J = 7.5, 2.0 Hz, 1H), 7.10 (dq, J = 9.0, 2.0 Hz, 1H), 6.93-6.97 (m, 1H), 6.76 (s, 2H), 4.74 (dt, J = 12.5, 1.0 Hz, 1H), 4.52 (q, J = 6.5 Hz, 1H), 4.19 (d, J = 12.5 Hz, 1H), 1.51 (d, J = 7.0 Hz, 3H). 2-312 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.37-7.41 (m, 2H), 7.17 − 7.25 (m, 2H), 6.75 (s, 2H), 5.58 − 5.65 (m, 1H), 4.58 − 4.69 (m, 2H), 1.49 (d, J = 7.0 Hz, 3H). 2-313 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.41-7.45 (m, 2H), 7.08 − 7.16 (m, 2H), 6.76 (s, 2H), 4.64 (dt, J = 12.0, 1.0 Hz, 1H), 4.58 (q, J = 7.0 Hz, 1H), 4.11 (d, J = 12.5 Hz, 1H), 1.51 (d, J = 7.0 Hz, 3H). 2-314 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.39 − 7.49 (m, 2H), 7.24 (td, J = 7.5, 2.0 Hz, 1H), 7.10 (td, J = 7.5, 2.0 Hz, 1H), 6.77 (s, 2H), 5.56 (d, J = 12.5 Hz, 1H), 4.85 (dd, J = 12.5, 1.0 Hz, 1H), 4.64 (q, J = 7.0 Hz, 1H), 1.52 (d, J = 7.0 Hz, 3H). 2-315 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.39 (dd, J = 7.5, 2.0 Hz, 1H), 7.24-7.28 (m, 1H), 7.18 (td, J = 7.5, 2.0 Hz, 1H), 7.03 (td, J = 7.5, 2.0 Hz, 1H), 6.77 (s, 2H), 5.00 (q, J = 7.0 Hz, 1H), 4.64 (dd, J = 12.5,1.0 Hz, 1H), 4.37 (dd, J = 12.5, 1.0 Hz, 1H), 1.54 (d, J = 7.0 Hz, 3H). 2-316 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.51 (q, J = 1.5 Hz, 1H), 7.27 − 7.34(m, 3H), 6.80 (s, 2H), 5.82 (d, J = 12.5 Hz, 1H), 4.64 (q, J = 7.0 Hz, 1H), 4.52 (d, J = 12.5 Hz, 1H), 1.47 (d, J = 6.5 Hz, 3H). 2-317 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.54 (q, J = 1.5 Hz, 1H), 7.25 − 7.37(m, 3H), 6.79 (s, 2H), 4.72 (dt, J = 12.5, 1.0 Hz, 1H), 4.49(q, J = 7.0 Hz, 1H), 4.19 (d, J = 12.5 Hz, 1H), 1.51 (d, J = 7.0 Hz, 3H). 2-318 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.40 − 7.47 (m, 2H), 7.31 − 7.37 (m, 2H), 6.75 (s, 2H), 5.73 (dt, J = 12.5, 1.0 Hz, 1H), 4.65 (q, J = 6.5 Hz, 1H), 4.56 (d, J = 12.5 Hz, 1H), 1.48 (d, J = 7.0 Hz, 3H). 2-319 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.37 − 7.44 (m, 2H), 7.31 − 7.37 (m, 2H), 6.75 (s, 2H), 5.03 (q, J = 7.0 Hz, 1H), 4.68 (d, J = 12.5 Hz, 1H), 4.15 (dt, J = 12.5, 1.2 Hz, 1H), 1.50 (d, J = 7.0 Hz, 3H). 2-320 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.65 (dd, J = 7.5, 2.0 Hz, 1H), 7.40-7.42 (m, 1H), 7.32 (td, J = 7.5, 2.0 Hz, 1H), 7.25 (td, J = 7.5, 2.0 Hz, 1H), 6.77 (s, 2H), 5.58 (d, J = 12.5 Hz, 1H), 4.88 (dd, J = 12.5, 1.0 Hz, 1H), 4.66 (q, J = 7.0 Hz, 1H), 1.54 (d, J = 7.0 Hz, 3H). 2-321 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.50 (dd, J = 7.5, 1.5 Hz, 1H), 7.26 − 7.35 (m, 2H), 7.13 − 7.22 (m, 1H), 6.77 (s, 2H), 5.22 (d, J = 12.5 Hz, 1H), 5.04 (q, J = 7.0 Hz, 1H), 4.05 − 4.12(m, 1H), 1.50 (d, J = 7.0 Hz, 3H). 2-322 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.61 (q, J = 2.0 Hz, 1H), 7.51 (dt, J = 7.5, 2.0 Hz, 1H), 7.45 (dq, J = 7.5, 2.0 Hz, 1H), 7.28 (t, J = 7.5 Hz, 1H), 6.83 (s, 2H), 5.81 (dt, J = 12.5, 1.0 Hz, 1H), 4.64 (q, J = 7.0 Hz, 1H), 4.49 (d, J = 12.5 Hz, 1H), 1.47 (d, J = 7.0 Hz, 3H). 2-323 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.39 − 7.49 (m, 3H), 7.22 (t, J = 7.5 Hz, 1H), 6.83 (s, 2H), 4.71 (dt, J = 12.5, 1.0 Hz, 1H), 4.48 (q, J = 7.0 Hz, 1H), 4.16 (d, J = 12.5 Hz, 1H), 1.51 (d, J = 7.0 Hz, 3H). 2-324 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.59 − 7.66 (m, 2H), 7.26 − 7.33 (m, 2H), 6.77 (s, 2H), 5.77 (dt, J = 12.5, 1.0 Hz, 1H), 4.65 (q, J = 7.0 Hz, 1H), 4.54 (d, J = 12.5 Hz, 1H), 1.48 (d, J = 7.0 Hz, 3H). 2-325 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.52 − 7.59 (m, 2H), 7.22 (dt, J = 7.5, 1.0 Hz, 2H), 6.77 (s, 2H), 4.99 (q, J = 7.0 Hz, 1H), 4.48 (dt, J = 12.5, 1.0 Hz, 1H), 4.13 (dt, J = 12.5, 1.0 Hz, 1H), 1.53 (d, J = 7.0 Hz, 3H). 2-327 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.56 − 7.62 (m, 1H), 7.49 (td, J = 7.5, 2.0 Hz, 1H), 7.37 − 7.46 (m, 2H), 6.77 (s, 2H), 5.55 (dd, J = 12.5, 1.0 Hz, 1H), 5.14 (dd, J = 12.5, 1.0 Hz, 1H), 4.63 (q, J = 7.0 Hz, 1H), 1.55 (d, J = 7.0 Hz, 3H). 2-328 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.52 (dd, J = 7.0, 2.0 Hz, 1H), 7.40 (td, J = 7.5, 2.0 Hz, 1H), 7.29 (t, J = 7.2 Hz, 2H), 6.77 (s, 2H), 5.01 (q, J = 7.0 Hz, 1H), 4.66 (d, J = 12.5 Hz, 1H), 4.55 (dd, J = 12.5, 1.0 Hz, 1H), 1.54 (d, J = 7.0 Hz, 3H). 2-329 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.65 (dd, J = 2.5, 1.5 Hz, 1H), 7.58 (dq, J = 5.5, 3.0 Hz, 1H), 7.50 (s, 1H), 7.49 (d, J = 3.0 Hz, 1H), 6.77 (s, 2H), 5.09 − 5.18 (m, 2H), 4.64 (q, J = 7.0 Hz, 1H), 1.51 (d, J = 6.5 Hz, 3H). 2-330 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.60 (d, J = 2.0 Hz, 1H), 7.50 − 7.57 (m, 1H), 7.38 − 7.46 (m, 2H), 6.77 (s, 2H), 4.90 (q, J = 7.0 Hz, 1H), 4.59 (dt, J = 12.5, 1.0 Hz, 1H), 4.18 (dd, J = 12.5, 1.5 Hz, 1H), 1.55 (d, J = 7.0 Hz, 3H). 2-331 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.69 (d, J = 7.0 Hz, 2H), 7.52 − 7.58 (m, 2H), 6.78 (s, 2H), 5.18 (dt, J = 12.5, 1.0 Hz, 1H), 5.10 (d, J = 12.5 Hz, 1H), 4.65 (q, J = 7.0 Hz, 1H), 1.51 (d, J = 7.0 Hz, 3H). 2-332 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.59 − 7.65 (m, 2H), 7.40 − 7.46 (m, 2H), 6.78 (s, 2H), 5.02 (q, J = 7.0 Hz, 1H), 4.73 (d, J = 12.5 Hz, 1H), 4.19 (dt, J = 12.5, 1.0 Hz, 1H), 1.50 (d, J = 7.0 Hz, 3H). 2-333 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.71 − 7.78 (m, 1H), 7.60-7.66 (m, 3H), 6.77 (s, 2H), 5.59 (d, J = 12.5 Hz, 1H), 5.10 (d, J = 12.5 Hz, 1H), 4.63 (q, J = 7.0 Hz, 1H), 1.55 (d, J = 7.0 Hz, 3H). 2-334 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.64 (dd, J = 7.0, 2.0 Hz, 1H), 7.46 − 7.58 (m, 2H), 7.42 − 7.48 (m, 1H), 6.76 (s, 2H), 5.05 (q, J = 7.0 Hz, 1H), 4.76 (dd, J = 12.5, 1.0 Hz, 1H), 4.50 (dd, J = 12.5, 1.0 Hz, 1H), 1.52 (d, J = 7.0 Hz, 3H). 2-335 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.96 (q, J = 1.5 Hz, 1H), 7.86 (dt, J = 7.5, 2.0 Hz, 1H), 7.64-7.67 (m, 1H), 7.49 (t, J = 7.5 Hz, 1H), 6.77 (s, 2H), 5.69 (d, J = 12.5 Hz, 1H), 4.60 − 4.69 (m, 2H), 1.48 (d, J = 7.0 Hz, 3H). 2-336 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.76 − 7.84 (m, 2H), 7.62 − 7.69 (m, 1H), 7.45 (t, J = 7.5 Hz, 1H), 6.81 (s, 2H), 5.00 (q, J = 7.0 Hz, 1H), 4.75 (d, J = 12.5 Hz, 1H), 4.23 (dt, J = 12.5, 1.0 Hz, 1H), 1.52 (d, J = 7.0 Hz, 3H). 2-337 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.84 − 7.90 (m, 2H), 7.66 − 7.73 (m, 2H), 6.76 (s, 2H), 5.79 (dt, J = 12.5, 1.0 Hz, 1H), 4.62 − 4.70 (m, 2H), 1.49 (d, J = 7.0 Hz, 3H). 2-338 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.61 − 7.68 (m, 2H), 7.46 − 7.52 (m, 2H), 6.77 (s, 2H), 4.99 (q, J = 7.0 Hz, 1H), 4.75 (d, J = 12.5 Hz, 1H), 4.23 (dt, J = 12.5, 1.0 Hz, 1H), 1.52 (d, J = 7.0 Hz, 3H). 2-339 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.95 − 8.02 (m, 2H), 7.82 − 7.90 (m, 2H), 7.81 (dd, J = 7.5, 1.5 Hz, 1H), 7.47 − 7.56 (m, 2H), 6.11 (s, 2H), 5.07 (q, J = 7.0 Hz, 1H), 1.46 (d, J = 7.0 Hz, 3H). 2-340 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.01-8.04 (m, 1H), 7.90 − 7.99 (m, 3H), 7.66 (dt, J = 7.5, 1.0 Hz, 1H), 7.57 (dd, J = 5.5, 3.5 Hz, 2H), 5.92 (s, 2H), 5.53 (dt, J = 12.5, 1.0 Hz, 1H), 5.00 (d, J = 12.5 Hz, 1H), 4.69 (q, J = 7.0 Hz, 1H), 1.50 (d, J = 6.5 Hz, 3H). 2-341 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.02 (dt, J = 7.5, 1.5 Hz, 1H), 7.95 (dq, J = 7.0, 1.5 Hz, 2H), 7.66 (dt, J = 7.5, 1.5 Hz, 1H), 7.55 − 7.66 (m, 2H), 7.38 (td, J = 7.5, 1.5 Hz, 1H), 5.92 (s, 2H), 5.62 (d, J = 12.5 Hz, 1H), 5.14 (dd, J = 12.5, 1.0 Hz, 1H), 4.69 (q, J = 7.0 Hz, 1H), 1.55 (d, J = 7.0 Hz, 3H). 2-342 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.53 (dd, J = 5.0, 1.5 Hz, 1H), 7.75 (td, J = 8.0, 1.5 Hz, 1H), 7.51 (dt, J = 8.0, 1.5 Hz, 1H), 7.28-7.30 (m, 1H), 6.78 (s, 2H), 5.44 (dd, J = 12.5, 1.5 Hz, 1H), 5.18 (d, J = 12.5 Hz, 1H), 4.65 (q, J = 7.0 Hz, 1H), 1.51 (d, J = 7.0 Hz, 3H). 2-343 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.40 (dd, J = 5.0, 1.0 Hz, 1H), 7.67 (td, J = 8.0, 1.5 Hz, 1H), 7.49 (dt, J = 8.0, 1.5 Hz, 1H), 7.28-7.31 (m, 1H), 6.76 (s, 2H), 5.05 (d, J = 12.5 Hz, 1H), 5.00(q, J = 7.0 Hz, 1H), 4.13 (dd, J = 12.5, 1.5 Hz, 1H), 1.51 (d, J = 7.0 Hz, 3H). 2-344 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.58 (d, J = 5.0 Hz, 2H), 7.51 − 7.56 (m, 2H), 6.77 (s, 2H), 5.07 (dt, J = 12.5, 1.0 Hz, 1H), 4.94 (d, J = 12.5 Hz, 1H), 4.65 (q, J = 7.0 Hz, 1H), 1.51 (d, J = 7.0 Hz, 3H). 2-345 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.40 (d, J = 5.0 Hz, 2H), 7.38 (d, J = 5.0 Hz, 2H), 6.77 (s, 2H), 4.95 (q, J = 7.0 Hz, 1H), 4.48 (d, J = 12.5 Hz, 1H), 4.11 (d, J = 12.5 Hz, 1H), 1.54 (d, J = 7.0 Hz, 3H). 2-346 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.59 (dd, J = 5.0, 1.5 Hz, 1H), 8.43 (d, J = 1.0 Hz, 1H), 8.01 (dd, J = 8.0, 5.0 Hz, 1H), 7.53 (dt, J = 8.0, 1.5 Hz, 1H), 6.77 (s, 2H), 4.99 (d, J = 12.5 Hz, 1H), 4.93 (d, J = 12.5 Hz, 1H), 4.64 (q, J = 7.0 Hz, 1H), 1.51 (d, J = 7.0 Hz, 3H). 2-347 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.39 − 8.49 (m, 2H), 7.59 (dt, J = 8.0, 1.5 Hz, 1H), 7.36 (dd, J = 8.0, 5.0 Hz, 1H), 6.77 (s, 2H), 4.96 (q, J = 7.0 Hz, 1H), 4.46 (d, J = 12.5 Hz, 1H), 4.10 (d, J = 12.5 Hz, 1H), 1.54 (d, J = 7.0 Hz, 3H). 2-348 .sup.1H NMR (500 MHz, Chloroform-d) δ 7.41 (d, J = 2.0 Hz, 1H), 6.41 (d, J = 3.5 Hz, 1H), 6.36 (dd, J = 3.5, 2.0 Hz, 1H), 5.25 (q, J = 7.0 Hz, 1H), 5.20 − 5.08 (m, 4H), 1.63 (d, J = 7.0 Hz, 3H). 2-349 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.46 (d, J = 7.5 Hz, 1H), 7.25 (d, J = 1.5 Hz, 1H), 6.81 (s, 2H), 6.37 (dd, J = 7.5, 1.5 Hz, 1H), 5.47 (d, J = 12.5 Hz, 1H), 4.99 (d, J = 12.5 Hz, 1H), 4.69 (q, J = 7.0 Hz, 1H), 1.53 (d, J = 7.0 Hz, 3H). 2-350 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.35 (dd, J = 6.5, 2.0 Hz, 1H), 7.00 − 7.09 (m, 2H), 6.81 (s, 2H), 5.71 (d, J = 12.5 Hz, 1H), 5.20 (d, J = 12.5 Hz, 1H), 4.69 (q, J = 7.0 Hz, 1H), 1.54 (d, J = 7.0 Hz, 3H). 2-351 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.33 (d, J = 7.5 Hz, 1H), 7.05 − 7.12 (m, 2H), 6.81 (s, 2H), 5.51 (d, J = 12.5 Hz, 1H), 4.87 (d, J = 12.5 Hz, 1H), 4.71 (q, J = 7.0 Hz, 1H), 1.52 (d, J = 7.0 Hz, 3H). 2-352 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.82 (s, 2H), 5.84 (s, 1H), 4.69 (q, J = 7.0 Hz, 1H), 3.72 (s, 3H), 2.32 (s, 3H), 1.44 (d, J = 7.0 Hz, 3H). 2-353 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.53 (d, J = 7.5 Hz, 1H), 6.81 (s, 2H), 6.37 (dd, J = 7.5, 1.0 Hz, 1H), 5.40 − 5.47 (m, 1H), 5.03 (d, J = 12.5 Hz, 1H), 4.70 (q, J = 7.0 Hz, 1H), 3.75 (s, 3H), 1.55 (d, J = 7.0 Hz, 3H). 2-354 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.70 (t, J = 1.5 Hz, 1H),7.01 (t, J = 1.0 Hz, 1H), 6.81 (s, 2H), 5.00 − 5.07 (m, 2H), 4.69 (q, J = 7.0 Hz, 1H), 3.89 (s, 3H), 1.54 (d, J = 7.0 Hz, 3H). 2-355 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.19 − 7.28 (m, 2H), 7.15 − 7.21 (m, 1H), 7.09 − 7.29 (m, 1H), 6.77 (s, 2H), 4.71 (q, J = 7.0 Hz, 1H), 2.10(d, J = 1.0 Hz, 3H), 1.61 (d, J = 7.0 Hz, 3H). 2-357 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.71 (t, J = 2.0 Hz, 1H), 7.52 (dt, J = 7.5, 2.0 Hz, 1H), 7.36 (dt, J = 7.5, 2.0 Hz, 1H), 7.25 (t, J = 7.5 Hz, 1H), 6.74 (s, 2H), 5.04 (q, J = 7.0 Hz, 1H), 1.52 (d, J = 7.0 Hz, 3H). 2-358 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.61 − 7.67 (m, 2H), 6.93-7.00 (m, 2H), 6.73 (s, 2H), 5.06 (q, J = 7 .0 Hz, 1H), 3.79 (s, 3H), 1.51 (d, J = 7.0 Hz, 3H). 2-360 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.46 − 7.53 (m, 2H), 7.28 (t, J = 7.5 Hz, 1H), 7.15-7.18 (M, 1H), 6.77 (s, 2H), 4.98 (q, J = 7.0 Hz, 1H), 2.89 (tt, J = 8.0, 6.0 Hz, 1H), 1.45 (d, J = 7.0 Hz, 3H), 1.17-1.23 (m, 6H). 2-363 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 8.50 (d, J = 5.0 Hz, 2H), 7.76 (d, J = 5.0 Hz, 2H), 6.74 (s, 2H), 5.03 (q, J = 7.0 Hz, 1H), 1.51 (d, J = 7.0 Hz, 3H). 2-365 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.97 (s, 1H), 6.82 (s, 2H), 5.06 (q, J = 7.0 Hz, 1H), 3.90 (s, 3H), 2.14 (s, 3H), 1.53 (d, J = 7.0 Hz, 3H). 2-368 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 6.66 (dd, J = 7.5, 1.5 Hz, 1H), 6.29 (dd, J = 7.5, 1.5 Hz, 1H), 6.12 (t, J = 7.5 Hz, 1H), 5.07 (q, J = 7.0 Hz, 1H), 3.62 (s, 3H), 1.56 (d, J = 7.0 Hz, 3H). 2-370 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.80 (s, 2H), 4.98 (d, J = 12.5 Hz, 1H), 4.93 (d, J = 12.5 Hz, 1H), 4.66 (q, J = 6.5 Hz, 1H), 3.44-3.51 (m, 1H), 3.16-3.24 (m, 1H), 1.51 (d, J = 7.0 Hz, 3H), 1.05 (t, J = 8.0 Hz, 3H). 2-371 .sup.1H NMR (500 MHz, Chloroform-d) δ 6.76 (s, 1H), 4.61 (q, J = 6.5 Hz, 1H), 4.44 (s, 2H), 1.73 (d, J = 6.5 Hz, 3H), 1.66 (s, 2H). 2-372 .sup.1H NMR (500 MHz, Chloroform-d) δ 8.09 (s, 1H), 4.93 (s, 1H), 4.71 (q, J = 6.5 Hz, 1H), 4.47 (s, 2H), 3.63 (s, 3H), 1.71 (d, J = 6.5 Hz, 3H), 1.44(s, 9H). 2-373 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.46 (s, 2H), 6.79 (s, 2H), 5.02 (q, J = 7.0 Hz, 1H), 1.59 (d, J = 7.0 Hz, 3H). 2-376 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.12 (s, 1H), 4.99 (q, J = 7.0 Hz, 1H), 3.66 (dq, J = 12.5, 8.0 Hz, 2-377 .sup.1H), 3.28 (dq, J = 12.5, 8.0 Hz, 1H), 2.31 (s, 3H), 1.54 (d, J = 7.0 Hz, 3H), 1.26 (t, J = 8.0 Hz, 3H). 1H NMR (500 MHz, Chloroform-d) δ 9.90 (s, 1H), 4.64 (q, J = 7.0 Hz, 1H), 3.85 (s, 3H), 2.20 (s, 3H), 1.70 (d, J = 7.0 Hz, 3H). 2-378 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.55 (dd, J = 7.0, 2.0 Hz, 1H), 6.34 − 6.43 (m, 2H), 6.22 (s, 1H), 5.14 (d, J = 12.5 Hz, 1H), 4.67 (q, J = 7.0 Hz, 1H), 4.43 (d, J = 12.5 Hz, 1H), 3.72 (s, 3H), 1.53 (d, J = 7.0 Hz, 3H). 2-379 .sup.1H NMR (500 MHz, Chloroform-d) δ 7.95 − 7.98 (m, 3H), 7.52 − 7.56 (m, 2H), 7.29-7.33 (m, 1H), 4.56 (q, J = 7.0 Hz, 1H), 3.85 (s, 3H), 1.69 (d, J = 7.0 Hz, 3H). 2-381 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.93 − 8.00 (m, 2H), 7.55 − 7.63 (m, 1H), 7.50 − 7.58 (m, 2H), 4.63 (q, J = 7.0 Hz, 1H), 3.72 (s, 3H), 1.53 (d, J = 7.0 Hz, 3H). 2-383 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.04 (s, 2H), 4.41 (d, J = 8.5 Hz, 1H), 4.11-4.18 (m, 2H), 1.14-1.31 (m, 5H), 0.48-0.66 (m, 3H) 2-385 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 7.59-7.62 (m, 2H), 7.32-7.34 (m, 3H), 6.77 (s, 2H), 6.27 (d, J = 1.0 Hz, 1H), 2.31 (s, 3H). 2-386 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.96 (s, 2H), 5.10 (q, J = 7.0 Hz, 1H), 4.30-4.26 (m, 1H), 4.19-4.14 (m, 1H), 4.07-4.00 (m, 2H), 2.23 (s, 3H), 1.75 (s, 3H), 1.66 (s, 3H), 1.48 (d, J = 7.0 Hz, 3H). 2-387 .sup.1H NMR (500 MHz, DMSO-d.sub.6) δ 6.43 − 6.34 (m, 2H), 6.22 (s, 1H), 4.84 (d, J = 7.0 Hz, 1H), 4.70 − 4.62 (m, 2H), 3.26 (s, 3H), 1.51 (d, J = 7.0 Hz, 3H).

[0144] Several methods for preparing the compounds of the present invention are detailedly illustrated in the following schemes and examples. The starting materials can be purchased commercially or can be prepared by methods known in the literature or according to the detailed illustrations. Those skilled in the art will appreciate that other synthetic routes can also be utilized to synthesize the compounds of the present invention. Although specific starting materials and conditions in the synthetic route have been described below, they can be easily replaced with other similar starting materials and conditions, and various isomers of compounds and the like produced by variations or variants of the preparation methods of the present invention are included in the scope of the present invention. Additionally, the preparation methods described below can be further modified in accordance with the present disclosure, using conventional chemical methods well known to those skilled in the art. For example, appropriate groups are protected during the reaction, and the like.

[0145] The method examples are provided below to facilitate a further understanding of the preparation method of the present invention, and the specific materials, types and conditions used are determined to be further description of the present invention and are not intended to limit its rational scope. The reagents used for synthesizing the following compounds indicated in the table below are either commercially available or can be readily prepared by those skilled in the art.

[0146] The examples of representative compounds are as follows, the synthetic methods of other compounds are similar, and will not be described in detail here.

[0147] 1. Synthesis of Compounds 2-31 and 1-2

[0148] (1) Compound 2-31-1 (300 mg, 1.27 mmol), compound b (255 mg, 1.53 mmol), a catalytic amount of TBAB (10 mg), and DMF (20 mL) were added to a 50 mL round-bottom flask, heated to 85° C. and reacted for 12 hr. After completed reaction of the starting materials according to LC-MS detection, the reaction solution was cooled to room temperature, concentrated, and separated by column chromatography to obtain compound 2-31 (180 mg, yield 47%).

##STR00466##

[0149] (2) Compound 2-31 (0.5 g, 1.77 mmol), methanol (20 mL) were added to a 100 mL single-port flask, lithium hydroxide (74 mg, 1.77 mmol) was dissolved in 2 mL of water, and slowly added dropwise to the single-port flask at room temperature, followed by stirring at room temperature for 12 hr. After completed reaction of the starting materials according to LC-MS detection, the reaction solution was adjusted with 0.5M dilute HCl to pH=5-6, concentrated, and then extracted with water and ethyl acetate. The organic phase was dried, and concentrated to obtain compound 1-2 (400 mg) as a white solid.

##STR00467##

[0150] 2. Synthesis of Compound 2-45

[0151] (1) Compound 2-45-1 (1 g, 8.61 mmol), phosphorus oxybromide (3.7 g, 12.9 mmol) were added to a 50 mL round-bottom flask, heated to 60° C. and reacted for 5 hr. After completed reaction of the starting materials according to HPLC detection, the reaction solution was cooled to room temperature, and slowly poured into an ice-water bath, with the temperature being controlled at 0-10° C. during quenching. The aqueous phase was extracted with ethyl acetate (100 mL×2). The organic phase was dried and concentrated to obtain compound 2-45-2 (1.5 g, crude product). Without further purification, the compound was directly used in the next step.

##STR00468##

[0152] (2) Compound a (400 mg, 2.13 mmol), compound 2-45-2 (700 mg), a catalytic amount of TBAB (10 mg), and DMF (10 mL) were added to a 50 mL round-bottom flask, heated to 85° C. and reacted for 12 hr. After completed reaction of the starting materials according to LC-MS detection, the reaction solution was cooled to room temperature, and extracted with water (100 mL) and methyl tert-butyl ether (50 mL×2). The organic phase was dried, concentrated, and separated by column chromatography to obtain compound 2-45 (200 mg, yield 35%), as a white solid.

##STR00469##

[0153] 3. Synthesis of Compound 2-69

[0154] Compound a (0.5 g, 2.13 mmol), compound b (313 mg, 2.55 mmol), a catalytic amount of TBAB (10 mg), and DMF (10 mL) were added to a round-bottom flask, and stirred at room temperature 15° C. for 24 hr. When there was a small amount of starting materials remained according to LC-MS detection, a further treatment was made. The reaction solution was poured into 50 mL of water, and extracted with methyl tert-butyl ether twice (50 mL×2). The organic phase was dried, concentrated, and separated by column chromatography, to obtain compound 2-69 (300 mg, yield 50%), as a white solid.

##STR00470##

[0155] 4. Synthesis of Compound 2-319

[0156] With a reference to the synthesis method of compound 1-2, compound 1-26 was prepared, then compound 1-26 (400 mg, 1.49 mmol), compound 2-319-1 (219 mg, 1.49 mmol), DCC (459 mg, 2.24 mmol), and anhydrous DCM (20 mL) were added to a 100 mL round-bottom flask, and reacted at room temperature for 12 hr. After completed reaction of the starting materials according to LC-MS detection, the reaction solution was concentrated, and separated by column chromatography to obtain compound 2-319 (250 mg, yield 41%), as a white solid.

##STR00471##

[0157] 5. Synthesis of Compounds 2-378 and 1-71

[0158] (1) Compound 2-69 (200 mg, 0.71 mmol), compound c (145 mg, 0.85 mmol), potassium carbonate (1 eq), a catalytic amount of DMAP (10 mg), and acetonitrile (20 mL) were added to a 50 mL round-bottom flask, heated to 80° C. and reacted for 12 hr. After completed reaction of the starting materials according to LC-MS detection, the reaction solution was cooled to room temperature, concentrated, and separated by column chromatography to obtain compound 2-378 (150 mg, yield 50%), as a colorless oil.

##STR00472##

[0159] (2) Compound 2-378 (0.15 g, 0.43 mmol), methanol (20 mL) were added to a 100 mL single-port flask, lithium hydroxide (48 mg, 2 mmol) was dissolved in 2 mL water, and slowly added dropwise to the single-port flask at room temperature, followed by stirring at room temperature for 12 hr. After completed reaction of the starting materials according to LC-MS detection, the reaction solution was adjusted with 0.5M dilute HCl to pH=5-6, concentrated, and then extracted with water and ethyl acetate. The organic phase was dried and concentrated to obtain compound 1-71 (100 mg), as a white solid.

##STR00473##

[0160] Biological activity evaluation:

[0161] The activity level standard of plants destruction (i. e. growth inhibition rate) is as follows:

[0162] Level 5: the growth inhibition rate is greater than 85%;

[0163] Level 4: the growth inhibition rate is equal to or greater than 60% and less than 85%;

[0164] Level 3: the growth inhibition rate is equal to or greater than 40% and less than 60%;

[0165] Level 2: the growth inhibition rate is equal to or greater than 20% and less than 40%;

[0166] Level 1: the growth inhibition rate is equal to or greater than 5% and less than 20%;

[0167] Level 0: the growth inhibition rate is less than 5%;

[0168] The above described growth inhibition rate is fresh weight inhibition rate.

[0169] Post-emergence test experiment: Monocotyledonous and dicotyledonous weed seeds and main crop seeds (i. e. wheat, corn, rice, soybean, cotton, oilseed, millet and sorghum.) were put into a plastic pot loaded with soil. Then covered with 0.5-2 cm soil, the seeds were allowed to grow in good greenhouse environment. The test plants were treated at 2-3 leaf stage 2 weeks after sowing. The test compounds of the invention were dissolved with acetone respectively, then added with tween-80, and using 1.5 liters per hectare of an emulsible concentrate of methyl oleate as a synergist, and diluted by certain amount of water to certain concentration. The solution was sprayed to the plants with a sprayer. Then the plants were cultured for 3 weeks in the greenhouse, and the experiment result of weed controlling effect was listed in tables 4-5.

TABLE-US-00004 TABLE 4 Activity test results of compounds (1000 g a.i./ha) Abutilon Echinochloa Digitaria Monochoria theophrasti Galium No. crusgalli sanguinalis Vaginalis Medic. aparine 1-2 5 5 5 5 5 1-4 5 5 5 1-26 5 5 5 5 5 1-27 5 5 5 1-71 5 5 5 5 5 2-1 5 5 5 2-2 5 5 5 5 5 2-3 5 5 5 5 5 2-4 5 5 5 5 5 2-5 5 5 5 2-6 5 5 5 2-7 5 5 5 5 5 2-8 5 5 5 2-9 5 5 5 2-10 5 5 5 2-11 5 5 5 2-12 5 5 5 2-13 5 5 5 2-14 5 5 5 5 5 2-15 5 5 5 2-16 5 5 5 2-17 5 5 5 5 5 2-18 5 5 5 2-19 5 5 5 2-20 5 5 5 2-21 5 5 5 2-22 5 5 5 5 5 2-23 5 5 5 2-24 5 5 5 5 5 2-25 5 5 5 2-26 5 5 5 5 5 2-27 5 5 5 2-28 5 5 5 5 5 2-29 5 5 5 5 5 2-30 5 5 5 5 5 2-31 5 5 5 5 5 2-32 5 5 5 5 5 2-33 5 5 5 2-34 5 5 5 2-35 5 5 5 2-36 5 5 5 2-37 5 5 5 2-38 5 5 5 2-39 5 5 5 2-40 5 5 5 2-41 5 5 5 2-42 5 5 5 2-43 5 5 5 2-44 5 5 5 2-45 5 5 5 2-46 5 5 5 2-47 5 5 5 2-48 5 5 5 2-49 5 5 5 2-50 5 5 5 2-51 5 5 5 2-52 5 5 5 2-53 5 5 5 2-54 5 5 5 2-55 5 5 5 2-56 5 5 5 2-57 5 5 5 2-58 5 5 5 2-59 5 5 5 2-60 5 5 5 2-61 5 5 5 2-62 5 5 5 2-63 5 5 5 2-64 5 5 5 2-65 5 5 5 2-67 5 5 5 2-68 5 5 5 2-69 5 5 5 5 5 2-70 5 5 5 5 5 2-71 5 5 5 5 5 2-72 5 5 5 5 5 2-73 5 5 5 5 5 2-74 5 5 5 5 5 2-75 5 5 5 5 5 2-76 5 5 5 5 5 2-77 5 5 5 5 5 2-78 5 5 5 5 5 2-79 5 5 5 5 5 2-80 5 5 5 5 5 2-81 5 5 5 5 5 2-82 5 5 5 5 5 2-83 5 5 5 5 5 2-84 5 5 5 5 5 2-85 5 5 5 5 5 2-86 5 5 5 5 5 2-87 5 5 5 5 5 2-88 5 5 5 5 5 2-89 5 5 5 5 5 2-90 5 5 5 5 5 2-91 5 5 5 5 5 2-92 5 5 5 5 5 2-93 5 5 5 5 5 2-94 5 5 5 5 5 2-95 5 5 5 5 5 2-96 5 5 5 5 5 2-97 5 5 5 5 5 2-98 5 5 5 5 5 2-99 5 5 5 5 5 2-100 5 5 5 5 5 2-101 5 5 5 5 5 2-102 5 5 5 5 5 2-103 5 5 5 5 5 2-104 5 5 5 5 5 2-105 5 5 5 5 5 2-106 5 5 5 5 5 2-107 5 5 5 5 5 2-108 5 5 5 5 5 2-113 5 5 5 5 5 2-114 5 5 5 5 5 2-121 5 5 5 5 5 2-122 5 5 5 5 5 2-155 5 5 5 5 5 2-156 5 5 5 5 5 2-157 5 5 5 5 5 2-158 5 5 5 5 5 2-159 5 5 5 5 5 2-160 5 5 5 5 5 2-163 5 5 5 5 5 2-164 5 5 5 5 5 2-175 5 5 5 5 5 2-176 5 5 5 5 5 2-195 5 5 5 5 5 2-196 5 5 5 5 5 2-215 5 5 5 5 5 2-216 5 5 5 5 5 2-235 5 5 5 5 5 2-236 5 5 5 5 5 2-263 5 5 5 5 5 2-264 5 5 5 5 5 2-265 5 5 5 5 5 2-266 5 5 5 5 5 2-267 5 5 5 5 5 2-268 5 5 5 5 5 2-270 5 5 5 5 5 2-271 5 5 5 5 5 2-272 5 5 5 5 5 2-273 5 5 5 5 5 2-274 5 5 5 5 5 2-275 5 5 5 5 5 2-276 5 5 5 5 5 2-277 5 5 5 5 5 2-278 5 5 5 5 5 2-279 5 5 5 5 5 2-280 5 5 5 5 5 2-281 5 5 5 5 5 2-282 5 5 5 5 5 2-283 5 5 5 5 5 2-284 5 5 5 5 5 2-285 5 5 5 5 5 2-286 5 5 5 5 5 2-287 5 5 5 5 5 2-288 5 5 5 5 5 2-289 5 5 5 5 5 2-290 5 5 5 5 5 2-291 5 5 5 5 5 2-292 5 5 5 5 5 2-294 5 5 5 5 5 2-295 5 5 5 5 5 2-296 5 5 5 5 5 2-297 5 5 5 5 5 2-298 5 5 5 5 5 2-299 5 5 5 5 5 2-300 5 5 5 5 5 2-301 5 5 5 5 5 2-302 5 5 5 5 5 2-303 5 5 5 5 5 2-304 5 5 5 5 5 2-305 5 5 5 5 5 2-306 5 5 5 5 5 2-307 5 5 5 5 5 2-308 5 5 5 5 5 2-309 5 5 5 5 5 2-310 5 5 5 5 5 2-311 5 5 5 5 5 2-312 5 5 5 5 5 2-313 5 5 5 5 5 2-314 5 5 5 5 5 2-315 5 5 5 5 5 2-316 5 5 5 5 5 2-317 5 5 5 5 5 2-318 5 5 5 5 5 2-319 5 5 5 5 5 2-320 5 5 5 5 5 2-321 5 5 5 5 5 2-322 5 5 5 5 5 2-323 5 5 5 5 5 2-324 5 5 5 5 5 2-325 5 5 5 5 5 2-327 5 5 5 5 5 2-328 5 5 5 5 5 2-329 5 5 5 5 5 2-330 5 5 5 5 5 2-331 5 5 5 5 5 2-332 5 5 5 5 5 2-333 5 5 5 5 5 2-334 5 5 5 5 5 2-335 5 5 5 5 5 2-336 5 5 5 5 5 2-337 5 5 5 5 5 2-338 5 5 5 5 5 2-339 5 5 5 5 5 2-340 5 5 5 5 5 2-341 5 5 5 5 5 2-342 5 5 5 5 5 2-343 5 5 5 5 5 2-344 5 5 5 5 5 2-345 5 5 5 5 5 2-346 5 5 5 5 5 2-347 5 5 5 5 5 2-348 5 5 5 5 5 2-349 5 5 5 5 5 2-350 5 5 5 5 5 2-351 5 5 5 5 5 2-352 5 5 5 5 5 2-353 5 5 5 5 5 2-354 5 5 5 5 5 2-355 5 5 5 5 5 2-357 5 5 5 5 5 2-358 5 5 5 5 5 2-360 5 5 5 5 5 2-363 5 5 5 5 5 2-365 5 5 5 5 5 2-368 5 5 5 5 5 2-370 5 5 5 5 5 2-371 5 5 5 5 5 2-372 5 5 5 5 5 2-373 5 5 5 5 5 2-376 5 5 5 5 5 2-377 5 5 5 5 5 2-378 5 5 5 5 5 2-379 5 5 5 5 5 2-381 5 5 5 5 5 2-383 5 5 5 2-385 5 5 5 2-386 5 5 5 5 5 2-387 5 5 5 5 5

TABLE-US-00005 TABLE 5 Post-emergence comparative activity test Semen Echinochloa Digitaria Euphorbiae No. crusgalli sanguinalis Lathyridis rice 1-2  5 5 5 N [00474] 2 3 3 N [00475] 1 1 1 N 1-26  5 5 5 0 1-26 (400 g a.i./ha) 5 5 5 3 [00476] 2 3 3 2 [00477] 1 1 1 N 1-71  5 5 5 0 2-30  4 5 4 N [00478] 2 3 2 N [00479] 0 0 0 N 2-69  5 5 5 0 2-70  5 5 5 0 2-71  5 5 5 0 2-71 (400 g a.i./ha) 5 5 5 2 [00480] 2 2 3 1 [00481] 1 1 1 N 2-72  5 5 5 0 2-86  5 5 5 0 2-103 5 5 5 0 2-113 5 5 5 0 2-121 5 5 5 0 2-195 4 5 5 0 2-215 4 5 5 0 2-235 5 5 5 0 2-271 5 5 5 0 2-280 5 5 5 0 2-283 5 5 5 0 2-287 5 5 5 0 2-292 5 5 5 N 2-294 5 5 5 0 2-298 5 5 5 0 2-298 (400 g a.i./ha) 5 5 5 1 2-298 (100 g a.i./ha) 4 5 5 0 [00482] 3 N N 0 [00483] 1 N N N 2-300 5 5 5 0 2-319 5 5 5 0 2-343 5 5 5 0 2-348 5 5 5 0 bispyribac-sodium (100 g a.i./ha) 1 1 0 N cyhalofop-butyl (300 g a.i./ha) 1 1 1 0 Notes: An average value was obtained through three repetitive experiments, N represented missing of some data; if not clearly indicated, the application dose was active ingredient 200 g/ha, plus water 450 kg/ha. Echinochloa crusgalli collected from Jiangsu, China, was resistant to ALS inhibitor herbicides and ACCe herbicides, and Digitaria sanguinalis and Semen Euphorbiae Lathyridis also collected from Jiangsu were resistant to the ACCe herbicide cyhalofop-butyl.

[0170] Unexpectedly, although the compounds of the present invention were similar in structure to the control compounds, they had good effects and better selectivity for major gramineous weeds, broad-leaved weeds, and Cyperus rotundus in rice fields, and had excellent commercial value. In particular, they were still outstanding to control key weeds that were resistant to the ALS inhibitor bispyribac-sodium and the ACCe inhibitor cyhalofop-butyl. In addition, compared with the racemate and the S-isomer, the R-isomer of the present invention had significantly improved activity against gramineous weeds such as Echinochloa crusgalli, Digitaria sanguinalis and Semen euphorbiae Lathyridis, and had good selectivity for rice.

[0171] Experiment on Weed Effect in Pre-Emergence Stage

[0172] Seeds of monocotyledonous and dicotyledonous weeds and main crops (e. g. wheat, corn, rice, soybean, cotton, oilseed, millet and sorghum) were put into a plastic pot loaded with soil and covered with 0.5-2 cm soil. The test compounds of the present invention was dissolved with acetone, then added with tween-80, diluted by a certain amount of water to reach a certain concentration, and sprayed immediately after sowing. The obtained seeds were incubated for 4 weeks in the greenhouse after spraying and the test results were observed. It was observed that the herbicide mostly had excellent effect at the application rate of 250 g a.i./ha, especially to weeds such as Echinochloa crusgalli, Digitaria sanguinalis and Abutilon theophrasti, etc. Many compounds had good selectivity for corn, wheat, rice, soybean, oilseed rape, etc.

[0173] Through experiments, we found that the compounds of the present invention generally had better weed control effects, especially for major gramineous weeds such as Echinochloa crusgalli, Digitaria sanguinalis, and Setaria viridis, which are widely occurring in corn fields, rice fields and wheat fields, and major broad-leaved weeds such as Abutilon theophrasti, Rorippa indica and Bidens pilosa, and had excellent commercial value. In particular, we noticed that they had extremely high activity against broad-leaved weeds, such as Rorippa indica, Descurainia sophia, Capsella bursa-pastoris, Lithospermum arvense, Galium aparine and Stellaria media, which were resistant to ALS inhibitors.

[0174] Transplanted Rice Safety Evaluation and Weed Control Effect Evaluation in Rice Field:

[0175] Rice field soil was loaded into a 1/1,000,000 ha pot. The seeds of Monochoria vaginalis 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. 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 Monochoria vaginalis reached 0.5 leaf stage.

[0176] 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.

[0177] The fertility condition of Monochoria vaginalis 14 days and rice 21 days after the treatment of the compound of the invention with the naked eye. Evaluate the weed control effect with the aforementioned activity standard level of 0-5, many compounds exhibited excellent activity and selectivity.

TABLE-US-00006 TABLE 6 Test results of activity and safety (1000 g a.i /ha) No. rice Monochoria Vaginalis 1-2 0 5  1-26 0 5  1-71 0 5  2-69 0 5  2-70 0 5  2-71 0 5  2-294 0 5  2-300 0 5  2-319 0 5  2-343 0 5  2-348 0 5 penoxsulam (50 g a.i./ha) 1 1

[0178] Note: The seeds of Monochoria vaginalis were collected from Heilongjing Province of China.

[0179] Tests indicated that the weeds were resistant to common rate of pyrazosulfuron-ethyl and penoxsulam.

[0180] It can be seen from the experiments that the compounds of the present invention had excellent activity against weeds having an anti-ALS inhibiting activity which cause a serious challenge in production, and can solve the increasingly serious problem of resistance.

[0181] 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 weeds such as Zoysia japonica, Cynodon dactylon, Festuca elata, Poa annua, Lolium perenne and Paspalum vaginatum etc, and is able to control many important gramineous weeds and broad-leaved weeds. The compound also shows 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.