Pyridyloxy-carboxylate derivative and preparation method therefor, herbicidal composition, and use

Abstract

The invention relates to the field of pesticide technology, and in particular a type of pyridyloxy carboxylate derivative, preparation method, herbicidal composition and application thereof. The pyridyloxy carboxylate derivative is represented by formula I, ##STR00001## wherein, A, B each independently represent halogen, or alkyl or cycloalkyl with or without halogen; C represents hydrogen, halogen, alkyl or haloalkyl; Q represents halogen, cyano, cyanoalkyl, hydroxyalkyl, amino, nitro, formyl, alkyl with or without halogen or the like; M represents -alkyl-R, R represents unsubstituted or substituted heterocyclyl, aryl or heteroaryl; Y represents O or S; X represents nitro or NR.sub.1R.sub.2. The compound has excellent herbicidal activity and higher crop safety, especially good selectivity for key crops such as rice and soybean.

Claims

1. A pyridyloxy carboxylate derivative represented by formula I, ##STR00327## wherein, A, B each independently represent halogen; or alkyl or cycloalkyl with or without 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 with or without halogen; or unsubstituted or substituted aryl, heteroaryl, arylalkyl or heteroarylalkyl; M represents -alkyl-R, R represents unsubstituted or substituted heterocyclyl, aryl or heteroaryl; Y represents O or S; X 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 other 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 or 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 ##STR00328## R.sub.21, R.sub.24 each independently represent H or alkyl; R.sub.22, 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 other nitrogen atom; R.sub.25 represents alkyl.

2. The pyridyloxy carboxylate derivative according to claim 1, wherein A, B each independently represent halogen; or C1-C8 alkyl or C3-C8 cycloalkyl with or without 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 with or without halogen; or unsubstituted or substituted aryl, heteroaryl, aryl C1-C8 alkyl or heteroaryl C1-C8 alkyl; M represents (C1-C6)alkyl-R, R represents unsubstituted or substituted heterocyclyl, aryl or heteroaryl; Y represents O or S; X 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 ##STR00329## 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, ##STR00330## 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 and C1-C8 alkoxy; R.sub.18 represents H or C1-C8 alkyl; or N?CR.sub.17R.sub.18 represents ##STR00331## R.sub.21, R.sub.24 each independently represent H or C1-C8 alkyl; R.sub.22, R.sub.23 each independently represent H or C1-C8 alkyl; or NR.sub.22R.sub.23 represents ##STR00332## R.sub.25 represents C1-C8 alkyl; the term heterocyclyl refers to ##STR00333## with 0, 1 or 2 oxo groups; the term aryl refers to phenyl or naphthyl; the term heteroaryl refers to ##STR00334## ##STR00335## 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 or phenoxy that is unsubstituted or substituted by at least one group from the group consisting of halogen, alkyl and alkoxy; alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, OR, SR, -alkyl-OR, -alkyl-SR, COR, COOR, COSR, SOR, SO.sub.2R, OCOR or SCOR with or without 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 or dialkylphosphono with or without halogen; R each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl.

3. The pyridyloxy carboxylate derivative according to claim 2, wherein A, B each independently represent halogen; or C1-C6 alkyl or C3-C6 cycloalkyl with or without 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 with or without halogen; or unsubstituted or substituted aryl, heteroaryl, aryl C1-C6 alkyl or heteroaryl C1-C6 alkyl; M represents (C1-C2)alkyl-R, R represents unsubstituted or substituted heterocyclyl, aryl or heteroaryl; Y represents O or S; X 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 ##STR00336## 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, ##STR00337## 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 ##STR00338## R.sub.21, R.sub.24 each independently represent H or C1-C6 alkyl; R.sub.22, R.sub.23 each independently represent H or C1-C6 alkyl; or NR.sub.22R.sub.23 represents ##STR00339## R.sub.25 represents C1-C6 alkyl; the term heterocyclyl refers to ##STR00340## with 0, 1 or 2 oxo groups; the term aryl refers to phenyl or naphthyl; the term heteroaryl refers to ##STR00341## ##STR00342## 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 or phenoxy that is unsubstituted or substituted by at least one group from the group consisting of halogen, C1-C6 alkyl and 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 or SCOR with or without 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 cyclo alkenyl, 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 or di-C1-C6 alkylphosphono with or without 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 pyridyloxy carboxylate derivative according to claim 3, wherein A, 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; ##STR00343## 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; M represents (C1-C2)alkyl-R; R represents tetrahydrofuryl, pyridyl, ##STR00344## thienyl, furyl, naphthyl, and phenyl that is unsubstituted or substituted by at least one group selected from the group consisting of C1-C6 alkyl, halo C1-C6 alkyl and halogen; R represents C1-C6 alkyl or halo C1-C6 alkyl; Y represents O or S; X represents amino, C1-C6 alkylamino, C1-C6 alkylcarbonylamino, phenylcarbonylamino, benzylamino; or furylmethyleneamino that is unsubstituted or substituted by halo C1-C6 alkyl.

5. The pyridyloxy carboxylate derivative according to claim 4, wherein A, 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, ##STR00345## benzyl, naphthyl, furyl, thienyl, thiazolyl, pyridyl, pyrimidinyl; ##STR00346## that is unsubstituted or substituted by methyl; or phenyl that is unsubstituted or substituted by at least one group selected from the group consisting of methyl, trifluoromethyl, chloro and methoxy; M represents CH.sub.2R; R represents tetrahydrofuryl, pyridyl, ##STR00347## thienyl, furyl, naphthyl, and phenyl that is unsubstituted or substituted by trifluoromethyl, bromo, chloro, fluoro, cyano or methyl; R represents methyl, ethyl or difluoromethyl; Y represents O or S; X represents NH.sub.2, ##STR00348##

6. The pyridyloxy carboxylate derivative according to claim 5, which is selected from the compounds of formula I as follows: ##STR00349## TABLE-US-00008 No. A B C Q M X Y 1 F F F CH.sub.3 NH.sub.2 O 2 Cl Cl Cl CH.sub.3 NH.sub.2 O 3 Cl Cl H CH.sub.3 NH.sub.2 O 4 Cl Cl F CH.sub.3 NH.sub.2 O 5 Cl Cl CH.sub.3 CH.sub.3 NH.sub.2 O 6 Cl Cl CF.sub.3 CH.sub.3 NH.sub.2 S 7 CH.sub.3 CH.sub.3 F CH.sub.3 NH.sub.2 O 8 Et Et CF.sub.3 CH.sub.3 NH.sub.2 S 9 Cl H CH.sub.3 NH.sub.2 O 10 Cl Cl CH.sub.3 NH.sub.2 O 11 F CF.sub.3 CH.sub.3 NH.sub.2 O 12 Br Br F CH.sub.3 NH.sub.2 S 13 I I H CH.sub.3 NH.sub.2 O 14 F CH.sub.3 NH.sub.2 S 15 CF.sub.3 Cl F CH.sub.3 NH.sub.2 O 16 Cl CF.sub.3 H CH.sub.3 NH.sub.2 O 17 Cl Cl I CH.sub.3 NH.sub.2 S 18 Cl Br CH.sub.3 NH.sub.2 O 19 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 NH.sub.2 O 20 Cl CH.sub.3 F CH.sub.3 NH.sub.2 O 21 Cl CH.sub.3 H CH.sub.3 NH.sub.2 O 22 Cl F CH.sub.3 NH.sub.2 O 23 Cl Cl H CH.sub.3 NH.sub.2 S 24 Cl Cl Cl CH.sub.3 NH.sub.2 S 25 Cl Cl F Et NH.sub.2 O 26 Cl Cl F NH.sub.2 S 27 Cl Cl F NH.sub.2 O 28 Cl Cl F NH.sub.2 O 29 Cl Cl F NH.sub.2 O 30 Cl Cl F NH.sub.2 S 31 Cl Cl F NH.sub.2 O 32 Cl Cl F NH.sub.2 O 33 Cl Cl F NH.sub.2 S 34 Cl Cl F F NH.sub.2 O 35 Cl Cl F Cl NH.sub.2 O 36 Cl Cl F Br NH.sub.2 S 37 Cl Cl F NH.sub.2 O 38 Cl Cl F NH.sub.2 S 39 Cl Cl F NH.sub.2 O 40 Cl Cl F NH.sub.2 O 41 Cl Cl F CF.sub.3 NH.sub.2 O 42 Cl Cl F NH.sub.2 S 43 Cl Cl F CN NH.sub.2 O 44 Cl Cl F NH.sub.2 S 45 Cl Cl F NH.sub.2 NH.sub.2 O 46 Cl Cl F NH.sub.2 S 47 Cl Cl F NH.sub.2 O 48 Cl Cl F NH.sub.2 O 49 Cl Cl F NO.sub.2 NH.sub.2 O 50 Cl Cl F NH.sub.2 S 51 Cl Cl F NH.sub.2 O 52 Cl Cl F NH.sub.2 O 53 Cl Cl F NH.sub.2 O 54 Cl Cl F NH.sub.2 O 55 Cl Cl F NH.sub.2 S 56 Cl Cl F NH.sub.2 O 57 Cl Cl F NH.sub.2 O 58 Cl Cl F NH.sub.2 S 59 Cl Cl F NH.sub.2 O 60 Cl Cl F NH.sub.2 O 61 Cl Cl F NH.sub.2 S 62 Cl Cl F NH.sub.2 O 63 Cl Cl F NH.sub.2 O 64 Cl Cl F NH.sub.2 O 65 Cl Cl F NH.sub.2 S 66 Cl Cl F NH.sub.2 O 67 Cl Cl F CH.sub.3 NH.sub.2 S 68 Cl Cl F CH.sub.3 NH.sub.2 O 69 Cl Cl F CH.sub.3 NH.sub.2 O 70 Cl Cl F CH.sub.3 NH.sub.2 O 71 Cl Cl F CH.sub.3 NH.sub.2 S 72 Cl Cl F CH.sub.3 NH.sub.2 O 73 Cl Cl F CH.sub.3 NH.sub.2 S 74 Cl Cl F CH.sub.3 NH.sub.2 O 75 Cl Cl F CH.sub.3 NH.sub.2 O 76 Cl Cl F CH.sub.3 NH.sub.2 S 77 Cl Cl F CH.sub.3 NH.sub.2 O 78 Cl Cl F CH.sub.3 NH.sub.2 O 79 Cl Cl F CH.sub.3 NH.sub.2 O 80 Cl Cl F CH.sub.3 NH.sub.2 O 81 Cl Cl F CH.sub.3 NH.sub.2 S 82 Cl Cl F CH.sub.3 NH.sub.2 O 83 Cl Cl F CH.sub.3 NH.sub.2 O 84 Cl Cl F CH.sub.3 NH.sub.2 S 85 Cl Cl F CH.sub.3 NH.sub.2 O 86 Cl Cl F CH.sub.3 NH.sub.2 O 87 Cl Cl F CH.sub.3 NH.sub.2 S 88 Cl Cl F CH.sub.3 NH.sub.2 O 89 Cl Cl F CH.sub.3 NH.sub.2 O 90 Cl Cl F CH.sub.3 NH.sub.2 O 91 Cl Cl F CH.sub.3 NH.sub.2 O 92 Cl Cl F CH.sub.3 NH.sub.2 O 93 Cl Cl F CH.sub.3 NH.sub.2 O 94 Cl Cl F CH.sub.3 NH.sub.2 S 95 Cl Cl F CH.sub.3 NH.sub.2 S 96 Cl Cl F CH.sub.3 NH.sub.2 O 97 Cl Cl F CH.sub.3 NH.sub.2 S 98 Cl Cl F CH.sub.3 NH.sub.2 O 99 Cl Cl F CH.sub.3 NH.sub.2 O 100 Cl Cl F CH.sub.3 NH.sub.2 O 101 Cl Cl F CH.sub.3 NH.sub.2 O 102 Cl Cl F CH.sub.3 NH.sub.2 O 103 Cl Cl F CH.sub.3 NH.sub.2 S 104 Cl Cl F CH.sub.3 NH.sub.2 S 105 Cl Cl F CH.sub.3 NH.sub.2 O 106 Cl Cl F CH.sub.3 NH.sub.2 S 107 Cl Cl F CH.sub.3 NH.sub.2 O 108 Cl Cl F CH.sub.3 NH.sub.2 O 109 Cl Cl F CH.sub.3 NH.sub.2 S 110 Cl Cl F CH.sub.3 NH.sub.2 O 111 Cl Cl F CH.sub.3 NH.sub.2 O 112 Cl Cl F CH.sub.3 NH.sub.2 O 113 Cl Cl F CH.sub.3 NH.sub.2 S 114 Cl Cl F CH.sub.3 NH.sub.2 O 115 Cl Cl F CH.sub.3 NH.sub.2 O 116 Cl Cl F CH.sub.3 NH.sub.2 O 117 Cl Cl F CH.sub.3 NH.sub.2 O 118 Cl Cl F CH.sub.3 NH.sub.2 S 119 Cl Cl F CH.sub.3 NH.sub.2 S 120 Cl Cl F CH.sub.3 NH.sub.2 O 121 Cl Cl F CH.sub.3 NH.sub.2 O 122 Cl Cl F CH.sub.3 NH.sub.2 O 123 Cl Cl F CH.sub.3 NH.sub.2 S 124 Cl Cl F CH.sub.3 NH.sub.2 O 125 Cl Cl F CH.sub.3 NH.sub.2 S 126 Cl Cl F CH.sub.3 NH.sub.2 O 127 Cl Cl F CH.sub.3 NH.sub.2 O 128 Cl Cl F CH.sub.3 NH.sub.2 S 129 Cl Cl F CH.sub.3 NH.sub.2 O 130 Cl Cl F CH.sub.3 NH.sub.2 O 131 Cl Cl F CH.sub.3 NH.sub.2 O 132 Cl Cl F CH.sub.3 NH.sub.2 S 133 Cl Cl F CH.sub.3 NH.sub.2 O 134 Cl Cl F CH.sub.3 NH.sub.2 S 135 Cl Cl F CH.sub.3 NH.sub.2 O 136 Cl Cl F CH.sub.3 NH.sub.2 O 137 Cl Cl F CH.sub.3 NH.sub.2 S 138 Cl Cl F CH.sub.3 NH.sub.2 O 139 Cl Cl F CH.sub.3 NH.sub.2 S 140 Cl Cl F CH.sub.3 NH.sub.2 O 141 Cl Cl F CH.sub.3 NH.sub.2 O 142 Cl Cl F CH.sub.3 NH.sub.2 S 143 Cl Cl F CH.sub.3 NH.sub.2 O 144 Cl Cl F CH.sub.3 NH.sub.2 O 145 Cl Cl F CH.sub.3 NH.sub.2 S 146 Cl Cl F CH.sub.3 NH.sub.2 O 147 Cl Cl F CH.sub.3 NH.sub.2 O 148 Cl Cl F CH.sub.3 NH.sub.2 O 149 Cl Cl F CH.sub.3 NH.sub.2 S 150 Cl Cl F CH.sub.3 NH.sub.2 S 151 Cl Cl F CH.sub.3 NH.sub.2 O 152 Cl Cl F CH.sub.3 NH.sub.2 S 153 Cl Cl F CH.sub.3 NH.sub.2 O 154 Cl Cl F CH.sub.3 NH.sub.2 S 155 Cl Cl F CH.sub.3 NH.sub.2 O 156 Cl Cl F CH.sub.3 NH.sub.2 S 157 Cl Cl F CH.sub.3 NH.sub.2 O 158 Cl Cl F CH.sub.3 NH.sub.2 O 159 Cl Cl F CH.sub.3 NH.sub.2 S 160 Cl Cl F CH.sub.3 NH.sub.2 O 161 Cl Cl F CH.sub.3 NH.sub.2 S 162 Cl Cl F CH.sub.3 NH.sub.2 O 163 Cl Cl F CH.sub.3 NH.sub.2 O 164 Cl Cl F CH.sub.3 NH.sub.2 O 165 Cl Cl F CH.sub.3 NH.sub.2 S 166 Cl Cl F CH.sub.3 NH.sub.2 O 167 Cl Cl F CH.sub.3 NH.sub.2 O 168 Cl Cl F CH.sub.3 NH.sub.2 S 169 Cl Cl F CH.sub.3 NH.sub.2 O 170 Cl Cl F CH.sub.3 NH.sub.2 S 171 Cl Cl F CH.sub.3 NH.sub.2 O 172 Cl Cl F CH.sub.3 NH.sub.2 O 173 Cl Cl F CH.sub.3 NH.sub.2 O 174 Cl Cl F CH.sub.3 NH.sub.2 S 175 Cl Cl F CH.sub.3 NH.sub.2 O 176 Cl Cl F CH.sub.3 NH.sub.2 O 177 Cl Cl F CH.sub.3 NH.sub.2 O 178 Cl Cl F CH.sub.3 NH.sub.2 O 179 Cl Cl F CH.sub.3 NH.sub.2 S 180 Cl Cl F CH.sub.3 NH.sub.2 O 181 Cl Cl F CH.sub.3 NH.sub.2 O 182 Cl Cl F CH.sub.3 NH.sub.2 S 183 Cl Cl F CH.sub.3 NH.sub.2 O 184 Cl Cl F CH.sub.3 NH.sub.2 O 185 Cl Cl F CH.sub.3 NH.sub.2 S 186 Cl Cl F CH.sub.3 NH.sub.2 O 187 Cl Cl F CH.sub.3 NH.sub.2 O 188 Cl Cl F CH.sub.3 NH.sub.2 S 189 Cl Cl F CH.sub.3 NH.sub.2 O 190 Cl Cl F CH.sub.3 O 191 Cl Cl F CH.sub.3 S 192 Cl Cl F CH.sub.3 O 193 Cl Cl F CH.sub.3 O 194 Cl Cl F CH.sub.3 O 195 Cl Cl F CH.sub.3 O 196 Cl Cl F CH.sub.3 NH.sub.2 O 197 Cl Cl F CH.sub.3 NH.sub.2 O 198 Cl Cl F CH.sub.3 NH.sub.2 O 199 Cl Cl F CH.sub.3 NH.sub.2 O 200 Cl Cl F CH.sub.3 NH.sub.2 O 201 Cl Cl F CH.sub.3 NH.sub.2 O 202 Cl Cl F CH.sub.3 NH.sub.2 O 203 Cl Cl F CH.sub.3 NH.sub.2 O 204 Cl Cl F CH.sub.3 NH.sub.2 O 205 Cl Cl F CH.sub.3 NH.sub.2 O 206 Cl Cl F CH.sub.3 NH.sub.2 O 207 Cl Cl F CH.sub.3 NH.sub.2 O 208 Cl Cl F CH.sub.3 NH.sub.2 O 209 Cl Cl F CH.sub.3 NH.sub.2 O 210 Cl Cl F CH.sub.3 NH.sub.2 O 211 Cl Cl F CH.sub.3 NH.sub.2 O 212 Cl Cl F CH.sub.3 NH.sub.2 O 213 Cl Cl F CH.sub.3 NH.sub.2 O 214 Cl Cl F CH.sub.3 NH.sub.2 O 215 Cl Cl F CH.sub.3 NH.sub.2 O 216 Cl Cl F CH.sub.3 NH.sub.2 O 217 Cl Cl F CH.sub.3 NH.sub.2 O 218 Cl Cl F CH.sub.3 NH.sub.2 S 219 Cl Cl F CH.sub.3 NH.sub.2 S 220 Cl Cl F CH.sub.3 NH.sub.2 S 221 Cl Cl F CH.sub.3 NH.sub.2 S 222 Cl Cl F CH.sub.3 NH.sub.2 S 223 Cl Cl F CH.sub.3 NH.sub.2 S 224 Cl Cl F CH.sub.3 NH.sub.2 S 225 Cl Cl F CH.sub.3 NH.sub.2 S 226 Cl Cl F CH.sub.3 NH.sub.2 S 227 Cl Cl F CH.sub.3 NH.sub.2 S 228 Cl Cl F CH.sub.3 NH.sub.2 S 229 Cl Cl F CH.sub.3 NH.sub.2 S 230 Cl Cl F CH.sub.3 NH.sub.2 S 231 Cl Cl F CH.sub.3 NH.sub.2 S 232 Cl Cl F CH.sub.3 NH.sub.2 S 233 Cl Cl F CH.sub.3 NH.sub.2 S 234 Cl Cl F CH.sub.3 NH.sub.2 S 235 Cl Cl F CH.sub.3 NH.sub.2 S 236 Cl Cl F CH.sub.3 NH.sub.2 S 237 Cl Cl F CH.sub.3 NH.sub.2 S 238 Cl Cl F CH.sub.3 NH.sub.2 O 239 Cl Cl F CH.sub.3 S

7. A method of preparing the pyridyloxy carboxylate derivative of claim 1, comprising: (1) reacting a compound of formula III with a compound of formula II to obtain a compound of formula I as follows: ##STR00637## wherein, W represents an alkali metal; Hal represents a halogen; or (2) when X represents NR.sub.1R.sub.2 (wherein R.sub.1 and R.sub.2 are not hydrogen at the same time), reacting a compound of formula I-1 ##STR00638## with a corresponding halide to obtain a compound of formula I.

8. The method of claim 7, wherein in step (1), the reaction is carried out in the presence of a catalyst and a solvent.

9. The method of claim 8, wherein the catalyst is TBAB, and the solvent is one or more of the solvents selected from the group consisting of DCM, DCE, ACN, THF, and DMF.

10. The method of claim 7, wherein in step (2), the reaction is carried out in the presence of a base and a solvent, and a catalyst is optionally added during the reaction.

11. The method of claim 10, wherein the base is one or more of the bases 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 of the solvents 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.

12. A herbicidal composition, comprising (i) at least one pyridyloxy carboxylate derivative of claim 1; optionally further comprising (ii) at least one additional herbicide and/or safener, and/or (iii) at least one agrochemically acceptable formulation auxiliary.

13. A method for controlling a weed, comprising applying a herbicidally effective amount of at least one pyridyloxy carboxylate derivative of claim 1 on a plant or in a weed area.

14. The method of claim 13, wherein the plant is rice or soybean; or the weed is a gramineous weed, a broad-leaved weed, or a cyperaceae weed.

15. The method of claim 13, wherein the plant is japonica rice, indica rice, or soybean; or the weed is Echinochloa crusgalli, Digitaria sanguinalis, Monochoria Vaginalis, Abutilon theophrasti, Galium spurium, or Cyperus iria.

16. A method for controlling a weed in a useful crop, comprising applying at least one pyridyloxy carboxylate derivative of claim 1 to the useful crop or in a weed area.

17. The method of claim 16, wherein the useful crop is a genetically modified crop, or a crop treated by gene editing technology.

18. The method of claim 16, wherein the useful crop is rice or soybean; or the weed is a gramineous weed, a broad-leaved weed, or a cyperaceae weed.

19. The method of claim 16, wherein the useful crop is japonica rice, indica rice, or soybean; or the weed is Echinochloa crusgalli, Digitaria sanguinalis, Monochoria Vaginalis, Abutilon theophrasti, Galium spurium, or Cyperus iria.

Description

SPECIFIC MODE FOR CARRYING OUT THE INVENTION

(1) 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.

(2) In view of economics and variety of a compound, we preferably synthesized several compounds, part of which are listed in the following Table 1. The structure and information of a certain compound are shown in Tables 1-2. The compounds in Table 1 are listed for further explication of the present invention, other than any limit therefor. The subject of the present invention should not be interpreted by those skilled in the art as being limited to the following compounds.

(3) TABLE-US-00001 TABLE 1 The structure of compounds No. A B C Q M X Y 1 F F F CH.sub.3 NH.sub.2 O 2 Cl Cl Cl CH.sub.3 NH.sub.2 O 3 Cl Cl H CH.sub.3 0 NH.sub.2 O 4 Cl Cl F CH.sub.3 NH.sub.2 O 5 Cl Cl CH.sub.3 CH.sub.3 NH.sub.2 O 6 Cl Cl CF.sub.3 CH.sub.3 NH.sub.2 S 7 CH.sub.3 CH.sub.3 F CH.sub.3 NH.sub.2 O 8 Et Et CF.sub.3 CH.sub.3 NH.sub.2 S 9 Cl H CH.sub.3 NH.sub.2 O 10 Cl Cl CH.sub.3 NH.sub.2 O 11 F 0 CF.sub.3 CH.sub.3 NH.sub.2 O 12 Br Br F CH.sub.3 NH.sub.2 S 13 I I H CH.sub.3 NH.sub.2 O 14 F CH.sub.3 NH.sub.2 S 15 CF.sub.3 Cl F CH.sub.3 NH.sub.2 O 16 Cl CF.sub.3 H CH.sub.3 NH.sub.2 O 17 Cl Cl I CH.sub.3 NH.sub.2 S 18 Cl 0 Br CH.sub.3 NH.sub.2 O 19 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 NH.sub.2 O 20 Cl CH.sub.3 F CH.sub.3 NH.sub.2 O 21 Cl CH.sub.3 H CH.sub.3 NH.sub.2 O 22 Cl F CH.sub.3 NH.sub.2 O 23 Cl Cl H CH.sub.3 NH.sub.2 S 24 Cl Cl Cl CH.sub.3 NH.sub.2 S 25 Cl Cl F Et NH.sub.2 O 26 Cl Cl F 0 NH.sub.2 S 27 Cl Cl F NH.sub.2 O 28 Cl Cl F NH.sub.2 O 29 Cl Cl F NH.sub.2 O 30 Cl Cl F NH.sub.2 S 31 Cl Cl F 0 NH.sub.2 O 32 Cl Cl F NH.sub.2 O 33 Cl Cl F NH.sub.2 S 34 Cl Cl F F NH.sub.2 O 35 Cl Cl F Cl NH.sub.2 O 36 Cl Cl F Br NH.sub.2 S 37 Cl Cl F 0 NH.sub.2 O 38 Cl Cl F NH.sub.2 S 39 Cl Cl F NH.sub.2 O 40 Cl Cl F NH.sub.2 O 41 Cl Cl F CF.sub.3 NH.sub.2 O 42 Cl Cl F NH.sub.2 S 43 Cl Cl F CN 0 NH.sub.2 O 44 Cl Cl F NH.sub.2 S 45 Cl Cl F NH.sub.2 NH.sub.2 O 46 Cl Cl F NH.sub.2 S 47 Cl Cl F NH.sub.2 O 48 Cl Cl F NH.sub.2 O 49 Cl Cl F NO.sub.2 00 NH.sub.2 O 50 Cl Cl F 01 02 NH.sub.2 S 51 Cl Cl F 03 04 NH.sub.2 O 52 Cl Cl F 05 06 NH.sub.2 O 53 Cl Cl F 07 08 NH.sub.2 O 54 Cl Cl F 09 0 NH.sub.2 O 55 Cl Cl F NH.sub.2 S 56 Cl Cl F NH.sub.2 O 57 Cl Cl F NH.sub.2 O 58 Cl Cl F NH.sub.2 S 59 Cl Cl F 0 NH.sub.2 O 60 Cl Cl F NH.sub.2 O 61 Cl Cl F NH.sub.2 S 62 Cl Cl F NH.sub.2 O 63 Cl Cl F NH.sub.2 O 64 Cl Cl F 0 NH.sub.2 O 65 Cl Cl F NH.sub.2 S 66 Cl Cl F NH.sub.2 O 67 Cl Cl F CH.sub.3 NH.sub.2 S 68 Cl Cl F CH.sub.3 NH.sub.2 O 69 Cl Cl F CH.sub.3 NH.sub.2 O 70 Cl Cl F CH.sub.3 NH.sub.2 O 71 Cl Cl F CH.sub.3 NH.sub.2 S 72 Cl Cl F CH.sub.3 0 NH.sub.2 O 73 Cl Cl F CH.sub.3 NH.sub.2 S 74 Cl Cl F CH.sub.3 NH.sub.2 O 75 Cl Cl F CH.sub.3 NH.sub.2 O 76 Cl Cl F CH.sub.3 NH.sub.2 S 77 Cl Cl F CH.sub.3 NH.sub.2 O 78 Cl Cl F CH.sub.3 NH.sub.2 O 79 Cl Cl F CH.sub.3 NH.sub.2 O 80 Cl Cl F CH.sub.3 NH.sub.2 O 81 Cl Cl F CH.sub.3 NH.sub.2 S 82 Cl Cl F CH.sub.3 0 NH.sub.2 O 83 Cl Cl F CH.sub.3 NH.sub.2 O 84 Cl Cl F CH.sub.3 NH.sub.2 S 85 Cl Cl F CH.sub.3 NH.sub.2 O 86 Cl Cl F CH.sub.3 NH.sub.2 O 87 Cl Cl F CH.sub.3 NH.sub.2 S 88 Cl Cl F CH.sub.3 NH.sub.2 O 89 Cl Cl F CH.sub.3 NH.sub.2 O 90 Cl Cl F CH.sub.3 NH.sub.2 O 91 Cl Cl F CH.sub.3 NH.sub.2 O 92 Cl Cl F CH.sub.3 0 NH.sub.2 O 93 Cl Cl F CH.sub.3 NH.sub.2 O 94 Cl Cl F CH.sub.3 NH.sub.2 S 95 Cl Cl F CH.sub.3 NH.sub.2 S 96 Cl Cl F CH.sub.3 NH.sub.2 O 97 Cl Cl F CH.sub.3 NH.sub.2 S 98 Cl Cl F CH.sub.3 NH.sub.2 O 99 Cl Cl F CH.sub.3 NH.sub.2 O 100 Cl Cl F CH.sub.3 NH.sub.2 O 101 Cl Cl F CH.sub.3 NH.sub.2 O 102 Cl Cl F CH.sub.3 0 NH.sub.2 O 103 Cl Cl F CH.sub.3 NH.sub.2 S 104 Cl Cl F CH.sub.3 NH.sub.2 S 105 Cl Cl F CH.sub.3 NH.sub.2 O 106 Cl Cl F CH.sub.3 NH.sub.2 S 107 Cl Cl F CH.sub.3 NH.sub.2 O 108 Cl Cl F CH.sub.3 NH.sub.2 O 109 Cl Cl F CH.sub.3 NH.sub.2 S 110 Cl Cl F CH.sub.3 NH.sub.2 O 111 Cl Cl F CH.sub.3 NH.sub.2 O 112 Cl Cl F CH.sub.3 0 NH.sub.2 O 113 Cl Cl F CH.sub.3 NH.sub.2 S 114 Cl Cl F CH.sub.3 NH.sub.2 O 115 Cl Cl F CH.sub.3 NH.sub.2 O 116 Cl Cl F CH.sub.3 NH.sub.2 O 117 Cl Cl F CH.sub.3 NH.sub.2 O 118 Cl Cl F CH.sub.3 NH.sub.2 S 119 Cl Cl F CH.sub.3 NH.sub.2 S 120 Cl Cl F CH.sub.3 NH.sub.2 O 121 Cl Cl F CH.sub.3 NH.sub.2 O 122 Cl Cl F CH.sub.3 0 NH.sub.2 O 123 Cl Cl F CH.sub.3 NH.sub.2 S 124 Cl Cl F CH.sub.3 NH.sub.2 O 125 Cl Cl F CH.sub.3 NH.sub.2 S 126 Cl Cl F CH.sub.3 NH.sub.2 O 127 Cl Cl F CH.sub.3 NH.sub.2 O 128 Cl Cl F CH.sub.3 NH.sub.2 S 129 Cl Cl F CH.sub.3 NH.sub.2 O 130 Cl Cl F CH.sub.3 NH.sub.2 O 131 Cl Cl F CH.sub.3 NH.sub.2 O 132 Cl Cl F CH.sub.3 00 NH.sub.2 S 133 Cl Cl F CH.sub.3 01 NH.sub.2 O 134 Cl Cl F CH.sub.3 02 NH.sub.2 S 135 Cl Cl F CH.sub.3 03 NH.sub.2 O 136 Cl Cl F CH.sub.3 04 NH.sub.2 O 137 Cl Cl F CH.sub.3 05 NH.sub.2 S 138 Cl Cl F CH.sub.3 06 NH.sub.2 O 139 Cl Cl F CH.sub.3 07 NH.sub.2 S 140 Cl Cl F CH.sub.3 08 NH.sub.2 O 141 Cl Cl F CH.sub.3 09 NH.sub.2 O 142 Cl Cl F CH.sub.3 0 NH.sub.2 S 143 Cl Cl F CH.sub.3 NH.sub.2 O 144 Cl Cl F CH.sub.3 NH.sub.2 O 145 Cl Cl F CH.sub.3 NH.sub.2 S 146 Cl Cl F CH.sub.3 NH.sub.2 O 147 Cl Cl F CH.sub.3 NH.sub.2 O 148 Cl Cl F CH.sub.3 NH.sub.2 O 149 Cl Cl F CH.sub.3 NH.sub.2 S 150 Cl Cl F CH.sub.3 NH.sub.2 S 151 Cl Cl F CH.sub.3 NH.sub.2 O 152 Cl Cl F CH.sub.3 0 NH.sub.2 S 153 Cl Cl F CH.sub.3 NH.sub.2 O 154 Cl Cl F CH.sub.3 NH.sub.2 S 155 Cl Cl F CH.sub.3 NH.sub.2 O 156 Cl Cl F CH.sub.3 NH.sub.2 S 157 Cl Cl F CH.sub.3 NH.sub.2 O 158 Cl Cl F CH.sub.3 NH.sub.2 O 159 Cl Cl F CH.sub.3 NH.sub.2 S 160 Cl Cl F CH.sub.3 NH.sub.2 O 161 Cl Cl F CH.sub.3 NH.sub.2 S 162 Cl Cl F CH.sub.3 0 NH.sub.2 O 163 Cl Cl F CH.sub.3 NH.sub.2 O 164 Cl Cl F CH.sub.3 NH.sub.2 O 165 Cl Cl F CH.sub.3 NH.sub.2 S 166 Cl Cl F CH.sub.3 NH.sub.2 O 167 Cl Cl F CH.sub.3 NH.sub.2 O 168 Cl Cl F CH.sub.3 NH.sub.2 S 169 Cl Cl F CH.sub.3 NH.sub.2 O 170 Cl Cl F CH.sub.3 NH.sub.2 S 171 Cl Cl F CH.sub.3 NH.sub.2 O 172 Cl Cl F CH.sub.3 0 NH.sub.2 O 173 Cl Cl F CH.sub.3 NH.sub.2 O 174 Cl Cl F CH.sub.3 NH.sub.2 S 175 Cl Cl F CH.sub.3 NH.sub.2 O 176 Cl Cl F CH.sub.3 NH.sub.2 O 177 Cl Cl F CH.sub.3 NH.sub.2 O 178 Cl Cl F CH.sub.3 NH.sub.2 O 179 Cl Cl F CH.sub.3 NH.sub.2 S 180 Cl Cl F CH.sub.3 NH.sub.2 O 181 Cl Cl F CH.sub.3 NH.sub.2 O 182 Cl Cl F CH.sub.3 0 NH.sub.2 S 183 Cl Cl F CH.sub.3 NH.sub.2 O 184 Cl Cl F CH.sub.3 NH.sub.2 O 185 Cl Cl F CH.sub.3 NH.sub.2 S 186 Cl Cl F CH.sub.3 NH.sub.2 O 187 Cl Cl F CH.sub.3 NH.sub.2 O 188 Cl Cl F CH.sub.3 NH.sub.2 S 189 Cl Cl F CH.sub.3 NH.sub.2 O 190 Cl Cl F CH.sub.3 O 191 Cl Cl F CH.sub.3 0 S 192 Cl Cl F CH.sub.3 O 193 Cl Cl F CH.sub.3 O 194 Cl Cl F CH.sub.3 O 195 Cl Cl F CH.sub.3 O 196 Cl Cl F CH.sub.3 0 NH.sub.2 O 197 Cl Cl F CH.sub.3 NH.sub.2 O 198 Cl Cl F CH.sub.3 NH.sub.2 O 199 Cl Cl F CH.sub.3 NH.sub.2 O 200 Cl Cl F CH.sub.3 NH.sub.2 O 201 Cl Cl F CH.sub.3 NH.sub.2 O 202 Cl Cl F CH.sub.3 NH.sub.2 O 203 Cl Cl F CH.sub.3 NH.sub.2 O 204 Cl Cl F CH.sub.3 NH.sub.2 O 205 Cl Cl F CH.sub.3 NH.sub.2 O 206 Cl Cl F CH.sub.3 0 NH.sub.2 O 207 Cl Cl F CH.sub.3 NH.sub.2 O 208 Cl Cl F CH.sub.3 NH.sub.2 O 209 Cl Cl F CH.sub.3 NH.sub.2 O 210 Cl Cl F CH.sub.3 NH.sub.2 O 211 Cl Cl F CH.sub.3 NH.sub.2 O 212 Cl Cl F CH.sub.3 NH.sub.2 O 213 Cl Cl F CH.sub.3 NH.sub.2 O 214 Cl Cl F CH.sub.3 NH.sub.2 O 215 Cl Cl F CH.sub.3 NH.sub.2 O 216 Cl Cl F CH.sub.3 0 NH.sub.2 O 217 Cl Cl F CH.sub.3 NH.sub.2 O 218 Cl Cl F CH.sub.3 NH.sub.2 S 219 Cl Cl F CH.sub.3 NH.sub.2 S 220 Cl Cl F CH.sub.3 NH.sub.2 S 221 Cl Cl F CH.sub.3 NH.sub.2 S 222 Cl Cl F CH.sub.3 NH.sub.2 S 223 Cl Cl F CH.sub.3 NH.sub.2 S 224 Cl Cl F CH.sub.3 NH.sub.2 S 225 Cl Cl F CH.sub.3 NH.sub.2 S 226 Cl Cl F CH.sub.3 00 NH.sub.2 S 227 Cl Cl F CH.sub.3 01 NH.sub.2 S 228 Cl Cl F CH.sub.3 02 NH.sub.2 S 229 Cl Cl F CH.sub.3 03 NH.sub.2 S 230 Cl Cl F CH.sub.3 04 NH.sub.2 S 231 Cl Cl F CH.sub.3 05 NH.sub.2 S 232 Cl Cl F CH.sub.3 06 NH.sub.2 S 233 Cl Cl F CH.sub.3 07 NH.sub.2 S 234 Cl Cl F CH.sub.3 08 NH.sub.2 S 235 Cl Cl F CH.sub.3 09 NH.sub.2 S 236 Cl Cl F CH.sub.3 0 NH.sub.2 S 237 Cl Cl F CH.sub.3 NH.sub.2 S 238 Cl Cl F CH.sub.3 NH.sub.2 O 239 Cl Cl F CH.sub.3 S

(4) TABLE-US-00002 TABLE 2 .sup.1HNMR data of compounds No. 1HNMR 1 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.29-7.36 (m, 5H), 5.16-5.24 (m, 2H), 4.55 (q, J = 7.0 Hz, 1H), 3.50 (s, 2H), 1.67 (d, J = 7.0 Hz, 3H). 2 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 5H), 5.73 (d, J = 12.5 Hz, 1H), 4.55-4.65 (m, 2H), 4.43 (s, 2H), 1.61 (d, J = 7.0 Hz, 3H). 3 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.36 (m, 6H), 5.56 (d, J = 12.5 Hz, 1H), 4.83 (d, J = 12.5 Hz, 1H), 4.49 (q, J = 7.0 Hz, 1H), 4.40 (s, 2H), 1.65 (d, J = 7.0 Hz, 3H). 4 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 7.28-7.33 (m, 5H), 7.03(s, 2H), 5.17-5.20 (m, 3H), 1.53 (s, 3H). 5 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 5H), 5.25 (d, J = 12.5 Hz, 1H), 5.16 (d, J = 12.5 Hz, 1H), 4.54 (q, J = 7.0 Hz, 1H), 4.43 (s, 2H), 2.65 (s, 3H), 1.66 (d, J = 7.0 Hz, 3H). 6 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.46-7.53 (m, 2H), 7.28-7.32 (m, 2H), 7.18-7.21 (m, 1H), 4.98 (q, J = 7.0 Hz, 1H), 4.70 (dt, J = 12.5, 1.0 Hz, 1H), 4.46 (s, 2H), 4.27 (dt, J = 12.5, 1.0 Hz, 1H), 1.70 (d, J = 7.0 Hz, 3H). 7 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 7.27-7.38 (m, 5H), 6.36 (s, 2H), 5.17 (d, J = 12.5 Hz, 1H), 5.02 (d, J = 12.5 Hz, 1H), 4.65 (q, J = 7.0 Hz, 1H), 2.11 (s, 3H), 2.04 (s, 3H), 1.49 (d, J = 7.0 Hz, 3H). 8 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 7.21-7.34 (m, 5H), 6.36 (s, 2H), 5.05 (q, J = 7.0 Hz, 1H), 4.76 (d, J = 12.5 Hz, 1H), 4.11 (d, J = 12.5 Hz, 1H), 2.55-2.63 (m, 1H), 2.29-2.36(m, 1H), 2.16-2.23 (m, 1H), 1.69-1.77 (m, 1H), 1.49 (d, J =7.0 Hz, 3H), 1.19 (t, J = 8.0 Hz, 3H), 1.10 (t, J = 8.0 Hz, 3H). 9 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 7.27-7.38 (m, 5H), 7.13 (s, 1H), 6.36 (s, 2H), 5.75 (d, J = 12.5 Hz, 1H), 4.57 (q, J = 7.0 Hz, 1H), 4.50 (d, J = 12.5 Hz, 1H), 2.75-2.80 (m, 1H), 1.47 (d, J = 6.5 Hz, 3H), 1.12 (dd, J = 25.0, 7.0 Hz, 6H). 10 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ?7.27-7.38 (m, 5H), 6.36 (s, 2H), 5.76 (d, J = 12.5 Hz, 1H), 4.66 (q, J = 7.0 Hz, 1H), 4.50 (d, J = 12.5 Hz, 1H), 2.06 (p, J = 7.0 Hz, 1H), 1.43 (d, J =7.0 Hz, 3H), 0.94 (tt, J = 7.2, 4.5 Hz, 2H), 0.66-0.75 (m, 2H). 11 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ?7.27-7.38 (m, 5H), 6.36 (s, 2H), 5.27 (d, J = 12.5 Hz, 1H), 4.92 (d, J = 12.5 Hz, 1H), 4.64 (q, J = 7.0 Hz, 1H), 3.10 (p, J = 7.0 Hz, 1H), 1.49 (d, J = 7.0 Hz, 3H), 1.11 (dd, J = 25.0, 7.0 Hz, 6H). 12 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 7.21-7.33 (m, 5H), 6.59 (s, 2H), 4.87 (q, J = 7.0 Hz, 1H), 4.66 (d, J = 12.5 Hz, 1H), 4.16 (d, J = 12.5 Hz, 1H), 1.50 (d, J = 7.0 Hz, 3H). 13 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 7.92 (s, 1H), 7.27-7.38(m, 5H), 6.36 (s, 2H), 5.82 (d, J = 12.5 Hz, 1H), 4.59 (q, J =7.0 Hz, 1H), 4.42 (d, J = 12.5 Hz, 1H), 1.48 (d, J = 7.0 Hz, 3H). 14 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 7.21-7.34 (m, 5H), 6.36 (s, 2H), 4.56 (q, J = 7.0 Hz, 1H), 4.29 (d, J = 12.0 Hz, 1H), 3.83 (d, J = 12.5 Hz, 1H), 2.62 (t, J = 8.0 Hz, 2H), 2.04-2.09 (m, 1H), 1.60-1.68 (m, 2H), 1.53 (d, J = 6.5 Hz, 3H), 0.90-1.01 (m, 5H), 0.67-0.76 (m, 2H). 15 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 7.27-7.38(m, 5H), 6.36 (s, 2H), 5.72 (d, J = 12.5 Hz, 1H), 4.62 (q, J =7.0 Hz, 1H), 4.38 (d, J = 12.5 Hz, 1H), 1.39 (d, J = 7.0 Hz, 3H). 16 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 7.74 (s, 1H), 7.27-7.38 (m, 5H), 6.36 (s, 2H), 5.67 (d, J = 12.0 Hz, 1H), 4.61 (q, J = 7.0 Hz, 1H), 4.36 (d, J = 12.5 Hz, 1H), 1.39 (d, J = 7.0 Hz, 3H). 17 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ?7.21-7.38 (m, 5H), 6.76 (s, 2H), 4.97 (q, J =7.0 Hz, 1H), 4.63 (d, J = 12.5 Hz, 1H), 4.36 (d, J = 12.5 Hz, 1H), 1.53 (d, J = 7.0 Hz, 3H). 18 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 7.27-7.38 (m, 5H), 6.36 (s, 2H), 5.79 (d, J = 12.5 Hz, 1H), 4.63 (q, J = 7.0 Hz, 1H), 4.53 (d, J = 12.5 Hz, 1H), 2.06-2.21 (m, 2H), 1.56-1.71 (m, 1H), 1.30-1.45 (m, 4H), 0.94 (t, J = 8.0 Hz, 3H). 19 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 5H), 5.36 (d, J = 12.5 Hz, 1H), 5.09 (d, J = 12.5 Hz, 1H), 4.54 (q, J = 7.0 Hz, 1H), 3.50 (s, 2H), 2.65 (s, 3H), 2.14 (d, J = 5.0 Hz, 6H), 1.64 (d, J = 7.0 Hz, 3H). 20 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 5H), 5.25 (d, J = 12.5 Hz, 1H), 5.15 (d, J = 12.5 Hz, 1H), 4.55 (q, J = 7.0 Hz, 1H), 3.50 (s, 2H), 2.17 (s, 3H), 1.66 (d, J = 7.0 Hz, 3H). 21 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.51 (s, 1H), 7.27-7.38 (m, 5H), 5.23 (d, J = 12.5 Hz, 1H), 5.16 (d, J = 12.5 Hz, 1H), 4.53 (q, J = 7.0 Hz, 1H), 3.50 (s, 2H), 2.17 (s, 3H), 1.65 (d, J = 7.0 Hz, 3H). 22 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ?7.27-7.38 (m, 5H), 6.36 (s, 2H), 5.91 (d, J = 12.5 Hz, 1H), 4.70 (q, J = 7.0 Hz, 1H), 4.38 (d, J = 12.5 Hz, 1H), 2.04 (p, J = 7.0 Hz, 1H), 1.48 (d, J = 6.5 Hz, 3H), 0.92-1.01 (m, 2H), 0.65-0.74 (m, 2H). 23 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.60 (s, 1H), 7.46-7.53 (m, 2H), 7.26-7.34 (m, 2H), 7.16-7.24 (m, 1H), 4.98 (q, J = 7.0 Hz, 1H), 4.68 (dt, J = 12.5, 1.0 Hz, 1H), 4.43-4.35 (m, 3H), 1.69 (d, J = 7.0 Hz, 3H). 24 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.46-7.53 (m, 2H), 7.30 (t, J = 7.5 Hz, 2H), 7.16-7.24 (m, 1H), 4.97 (q, J = 7.0 Hz, 1H), 4.68 (dt, J = 12.5, 1.0 Hz, 1H), 4.42 (s, 2H), 4.32 (dt, J = 12.5, 1.0 Hz, 1H), 1.58 (d, J = 7.0 Hz, 3H). 25 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 5H), 5.17-5.22 (m, 2H), 4.51-4.53( m, 1H), 4.42 (s, 2H), 2.18-2.28 (m, 1H), 1.87-1.96 (m, 1H), 0.89 (t, J = 8.0 Hz, 3H). 26 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 5H), 5.16-5.26 (m, 2H), 4.42 (s, 2H), 4.30 (dd, J = 11.0, 1.5 Hz, 1H), 1.95-2.07 (m, 1H), 1.73-1.90 (m, 1H), 1.60-1.71 (m, 1H), 1.31-1.45 (m, 1H), 1.02 (t, J = 8.0 Hz, 3H). 27 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 5H), 5.30 (d, J = 12.5 Hz, 1H), 5.12 (dd, J = 12.5, 1.0 Hz, 1H), 4.41 (s, 2H), 4.34 (d, J = 7.0 Hz, 1H), 2.33-2.40 (m, 1H), 0.94-1.00 (m, 6H). 28 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 5H), 5.86 (d, J = 12.5 Hz, 1H), 4.60 (d, J = 12.5 Hz, 1H), 4.40 (s, 2H), 4.31 (d, J = 7.0 Hz, 1H), 0.92-0.99 (m, 1H), 0.49-0.53 (m, 2H), 0.36-0.41 (m, 2H). 29 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 5H), 5.94-6.00(m, 1H), 4.69 (t, J = 7.0 Hz, 1H), 4.53 (d, J = 12.5 Hz, 1H), 4.36 (s, 2H), 4.19 (dd, J = 12.5, 7.0 Hz, 1H), 3.92 (dd, J = 12.5, 7.0 Hz, 1H), 3.29 (s, 3H). 30 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.46-7.53 (m, 2H), 7.26-7.34 (m, 2H), 7.16-7.24 (m, 1H), 4.70- 4.77 (m, 1H), 4.47 (dd, J = 11.0, 1.0 Hz, 1H), 4.41 (s, 2H), 4.36 (d, J = 12.5 Hz, 1H), 3.44 (dt, J = 12.5, 7.0 Hz, 1H), 3.35 (s, 3H), 3.08 (dt, J = 12.5, 7.0 Hz, 1H), 2.20-2.28 (m, 1H), 1.84-1.91 (m, 1H). 31 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 5H), 5.75 (d, J = 12.5 Hz, 1H), 4.60 (d, J = 12.5 Hz, 1H), 4.39 (d, J = 7.0 Hz, 1H), 4.36 (s, 2H), 4.19 (p, J =7.0 Hz, 1H), 3.35 (s, 3H), 1.21 (d, J = 7.0 Hz, 3H). 32 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 5H), 6.09-6.15 (m, 1H), 5.90 (d, J = 12.5 Hz, 1H), 5.56-5.61 (m, 1H), 5.36-5.41 (m, 1H), 5.13-5.20 (m, 1H), 4.50 (d, J = 12.5 Hz, 1H), 4.40 (s, 2H). 33 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.46-7.53 (m, 2H), 7.30 (t, J = 7.5 Hz, 2H), 7.16-7.24 (m, 1H), 5.75 (d, J = 2.5 Hz, 1H), 4.80 (dt, J = 12.5, 1.0 Hz, 1H), 4.38 (s, 2H), 4.26 (d, J = 12.5 Hz, 1H), 2.59 (d, J = 2.5 Hz, 1H). 34 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 10H), 7.02 (s, 1H), 6.93 (s, 1H), 5.24 (d, J = 12.5 Hz, 2H), 5.19 (d, J = 12.5 Hz, 2H), 4.42 (s, 4H). 35 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 5H), 6.59 (s, 1H), 5.35-5.25 (m, 2H), 4.44 (s, 2H). 36 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.46-7.53 (m, 2H), 7.26-7.34 (m, 2H), 7.16-7.24 (m, 1H), 6.97 (s, 1H), 4.60-4.62 (m, 1H), 4.44 (s, 2H), 4.30 (d, J = 12.5 Hz, 1H). 37 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 5H), 5.69 (d, J = 12.5 Hz, 1H), 4.86 (d, J = 12.5 Hz, 1H), 4.81 (t, J = 7.0 Hz, 1H), 4.40 (s, 2H), 4.29 (dd, J = 12.5, 7.0 Hz, 1H), 4.02 (dd, J = 12.5, 7.0 Hz, 1H). 38 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.46-7.53 (m, 4H), 7.30 (t, J = 7.5 Hz, 4H), 7.16-7.24(m, 2H), 5.15 (dd, J = 12.5, 7.0 Hz, 1H), 4.84 (dd, J = 12.5, 7.0 Hz, 1H), 4.67-4.79 (m, 3H), 4.64 (dt, J = 12.5, 1.0 Hz, 2H), 4.42 (s, 4H), 4.35 (d, J = 12.5 Hz, 2H). 39 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 10H), 6.64 (d, J = 7.0 Hz, 1H), 5.39 (d, J = 12.5 Hz, 2H), 5.16 (d, J = 12.5 Hz, 2H), 4.81-4.91 (td, J = 20.9, 7.0 Hz, 2H), 4.42 (s, 4H). 40 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38(m, 5H), 5.36 (d, J = 12.5 Hz, 1H), 5.12 (d, J = 12.5 Hz, 1H), 4.42 (s, 2H), 4.35 (dd, J = 11.0, 1.5 Hz, 1H), 3.82 (td, J = 12.5, 2.5 Hz, 1H), 3.49 (td, J = 12.0, 4.0 Hz, 1H), 2.53-2.44 (m, 1H), 2.21-2.29 (m, 1H). 41 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 5H), 5.93 (d, J = 12.5 Hz, 1H), 5.15 (q, J = 9.0 Hz, 1H), 4.62 (d, J = 12.5 Hz, 1H), 4.40 (s, 2H). 42 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.46-7.53 (m, 2H), 7.30 (t, J = 7.5 Hz, 2H), 7.16-7.24 (m, 1H), 4.81 (dd, J = 10.5, 1.0 Hz, 1H), 4.72 (dd, J = 12.5, 1.0 Hz, 1H), 4.49 (dt, J = 12.5, 1.0 Hz, 1H), 4.42 (s, 2H), 2.86-2.94 (m, 1H), 2.50-2.60 (m, 1H). 43 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 5H), 5.75 (s, 1H), 5.30 (d, J = 12.5 Hz, 1H), 5.21 (d, J = 12.5 Hz, 1H), 4.42 (s, 2H). 44 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.46-7.53 (m, 2H), 7.26-7.34 (m, 2H), 7.16-7.24 (m, 1H), 5.84 (t, J = 7.0 Hz, 1H), 4.82 (dt, J = 12.5, 1.0 Hz, 1H), 4.39 (s, 2H), 4.31 (d, J = 12.5 Hz, 1H), 3.25 (dd, J = 12.5, 7.0 Hz, 1H), 2.99 (dd, J = 12.5, 7.0 Hz, 1H). 45 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 5H), 6.01-6.08 (m, 2H), 4.53 (d, J = 12.5 Hz, 1H), 4.38 (s, 2H), 1.56 (s, 2H). 46 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.46-7.53 (m, 2H), 7.26-7.34 (m, 2H), 7.16-7.24 (m, 1H), 4.95 (t, J = 7.0 Hz, 1H), 4.75 (d, J = 12.5 Hz, 1H), 4.40 (s, 2H), 4.34 (dt, J = 12.5, 1.0 Hz, 1H), 2.96 (dd, J = 12.5, 7.0 Hz, 1H), 2.38 (dd, J = 12.5, 7.0 Hz, 1H), 2.24 (s, 6H). 47 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 5H), 5.96 (d, J = 12.5 Hz, 1H), 5.89 (s, 1H), 4.55 (d, J = 12.5 Hz, 1H), 4.38 (s, 2H), 2.13 (s, 3H). 48 .sup.1H NMR (500 MHz, Chloroform-d) 6 7.27-7.38 (m, 5H), 5.95 (d, J = 12.5 Hz, 1H), 4.58 (d, J = 12.5 Hz, 1H), 4.52 (t, J = 7.0 Hz, 1H), 4.39 (s, 2H), 4.25-4.30 (m, 1H), 4.02-4.07 (m, 1H), 2.96 (t, J = 5.5 Hz, 1H). 49 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 5H), 7.24 (s, 1H), 5.24 (d, J = 12.5 Hz, 1H), 5.18 (d, J = 12.5 Hz, 1H), 4.42 (s, 2H). 50 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.46-7.53(m, 2H), 7.26-7.34 (m, 2H), 7.16-7.24 (m, 1H), 6.13 (s, 1H), 4.74 (dt, J = 12.5, 1.0 Hz, 1H), 4.41 (s, 2H), 4.29 (d, J = 12.5 Hz, 1H), 3.20 (s, 3H). 51 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 5H), 5.99 (d, J = 12.5 Hz, 1H), 5.80 (d, J = 6.0 Hz, 1H), 4.57 (d, J = 12.5 Hz, 1H), 4.38 (s, 2H). 52 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 5H), 5.59 (s, 1H), 5.47 (d, J = 12.5 Hz, 1H), 5.08 (d, J = 12.5 Hz, 1H), 4.43 (s, 2H), 3.76 (s, 3H). 53 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.18-7.38 (m, 10H), 5.24-5.34 (m, 2H), 4.84 (t, J = 7.0 Hz, 1H), 4.45 (s, 2H), 3.49-3.57 (m, 1H), 3.13-3.21 (m, 1H). 54 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 6H), 7.12 (dd, J = 7.5, 1.5 Hz, 1H), 7.06 (t, J = 7.5 Hz, 1H), 6.11 (s, 1H), 5.42 (d, J = 12.5 Hz, 1H), 5.09 (d, J = 12.5 Hz, 1H), 4.44 (s, 2H). 55 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.45-7.53 (m, 3H), 7.40 (d, J = 7.5 Hz, 1H), 7.30 (t, J = 7.5 Hz, 2H), 7.16-7.24 (m, 1H), 6.43 (dd, J = 7.5, 1.5 Hz, 1H), 6.18 (s, 1H), 4.85 (dd, J = 12.5, 1.1 Hz, 1H), 4.40 (s, 2H), 4.31 (d, J = 12.5 Hz, 1H). 56 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.97 (d, J = 3.0 Hz, 1H), 8.04 (d, J = 3.0 Hz, 1H), 7.46-7.53 (m, 2H), 7.26-7.34 (m, 2H), 7.16-7.24 (m, 1H), 6.81 (s, 1H), 4.81 (d, J = 12.5 Hz, 1H), 4.40 (s, 2H), 4.33 (dt, J = 12.5, 1.0 Hz, 1H). 57 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.46-7.53 (m, 2H), 7.24-7.34 (m, 3H), 7.16-7.24 (m, 1H), 6.71 (s, 1H), 5.86 (d, J = 7.5 Hz, 1H), 4.78 (dd, J = 12.5, 1.1 Hz, 1H), 4.65 (dq, J = 12.5, 8.0 Hz, 1H), 4.41 (s, 2H), 4.41 (d, J = 12.5 Hz, 1H), 4.28 (dq, J = 12.8, 8.0 Hz, 1H), 1.40 (t, J = 8.0 Hz, 3H). 58 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.46-7.53 (m, 2H), 7.26-7.34 (m, 2H), 7.16-7.24(m, 1H), 6.83 (s, 1H), 6.48 (s, 1H), 4.82 (dt, J = 12.5, 1.0 Hz, 1H), 4.42 (s, 2H), 4.35 (d, J = 12.5 Hz, 1H), 3.73 (s, 3H), 2.36 (s, 3H). 59 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.79 (s, 1H), 7.26-7.38 (m, 13H), 6.43 (d, J = 7.5 Hz, 2H), 5.96 (s, 2H), 5.39 (d, J = 12.5 Hz, 2H), 5.12 (d, J = 12.5 Hz, 2H), 4.44 (s, 4H). 60 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.59-7.66 (m, 2H), 7.37-7.47 (m, 4H), 7.27-7.38 (m, 6H), 5.91 (s, 1H), 5.37 (d, J = 12.5 Hz, 1H), 4.96 (d, J = 12.5 Hz, 1H), 4.46 (s, 2H). 61 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.49-7.61 (m, 6H), 7.18-7.32 (m, 3H), 6.34 (s, 1H), 4.67-4.74 (m, 1H), 4.45 (s, 2H), 4.29 (d, J = 12.5 Hz, 1H). 62 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.49-7.61 (m, 6H), 7.18-7.32 (m, 4H), 4.67-4.74 (m, 1H), 4.45 (s, 2H), 4.29 (d, J = 12.5 Hz, 1H). 63 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.39 (m, 6H), 6.76-6.85 (m, 2H), 6.06 (d, J = 1.0 Hz, 1H), 5.35 (d, J = 12.5 Hz, 1H), 5.03 (d, J = 12.5 Hz, 1H), 4.46 (s, 2H), 3.71 (s, 3H), 2.29 (d, J = 1.0 Hz, 3H). 64 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.49-7.71 (m, 4H), 7.18-7.32 (m, 6H), 4.67-4.74 (m, 1H), 4.45 (s, 2H), 4.29 (d, J = 12.5 Hz, 1H). 65 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.49-7.61 (m, 3H), 7.18-7.32 (m, 5H), 4.67-4.74 (m, 1H), 4.45 (s, 2H), 4.29 (d, J = 12.5 Hz, 1H). 66 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.05 (t, J = 1.5 Hz, 1H), 7.84-7.88 (m, 2H), 7.75-7.80 (m, 2H), 7.40- 7.49 (m, 2H), 7.27-7.28 (m, 5H), 6.00 (s, 1H), 5.32 (d, J = 12.5 Hz, 1H), 5.05 (d, J = 12.5 Hz, 1H), 3.79 (s, 2H). 67 .sup.1H NMR (500 MHz, Chloroform-d) ? 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). 68 .sup.1H NMR (500 MHz, Chloroform-d) ? 4.57 (q, J = 7.0 Hz, 1H), 4.45 (s, 2H), 4.38-4.26 (m, 2H), 4.02- 3.91 (m, 1H), 3.88-3.79 (m, 1H), 3.72-3.76 (m, 1H), 2.12-1.94 (m, 2H), 1.74-1.62 (m, 4H), 1.54-1.44 (m, 1H). 69 .sup.1H NMR (500 MHz, Chloroform-d) ? 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). 70 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.33 (t, J = 7.5 Hz, 1H), 7.17-7.28 (m, 2H), 6.69 (s, 1H), 5.45 (dd, J = 12.5, 1.0 Hz, 1H), 5.00 (dt, J = 12.5, 1.0 Hz, 1H), 4.69 (q, J = 7.0 Hz, 1H), 4.47 (s, 2H), 2.62-2.74 (m, 1H), 2.38-2.50 (m, 1H), 1.62 (d, J = 7.0 Hz, 3H), 1.27 (t, J = 8.0 Hz, 3H). 71 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.24-7.35 (m, 2H), 7.13-7.23 (m, 2H), 4.94 (q, J = 7.0 Hz, 1H), 4.75 (d, J = 12.5 Hz, 1H), 4.41 (s, 2H), 4.33 (dt, J = 12.5, 1.0 Hz, 1H), 2.84-2.91 (m, 1H), 1.47 (d, J = 7.0 Hz, 3H), 1.19-1.25 (m, 6H). 72 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.45-7.52 (m, 2H), 7.26-7.32 (m, 2H), 5.85 (d, J = 12.5 Hz, 1H), 4.64 (q, J = 7.0 Hz, 1H), 4.44 (dt, J = 12.5, 1.0 Hz, 1H), 4.43 (s, 2H), 2.83-2.89 (m, 1H), 1.53 (d, J = 7.0 Hz, 3H), 1.17-1.23 (m, 6H). 73 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.14-7.18(m, 4H), 6.30-6.33 (m, 1H), 5.83-5.90 (m, 1H), 4.93 (q, J = 6.8 Hz, 1H), 4.76 (d, J = 12.5 Hz, 1H), 4.41 (s, 2H), 4.35 (dt, J = 12.5, 1.0 Hz, 1H), 1.70 (dd, J = 6.5, 1.0 Hz, 3H), 1.46 (d, J = 7.0 Hz, 3H). 74 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.19-7.26 (m, 2H), 7.06-7.13 (m, 2H), 4.95 (q, J = 7.0 Hz, 1H), 4.70 (d, J = 12.5 Hz, 1H), 4.44 (s, 2H), 4.31 (d, J = 12.5 Hz, 1H), 1.82-1.87 (m, 1H), 1.43 (d, J = 7.0 Hz, 3H), 1.09-1.18 (m, 2H), 0.80-0.89 (m, 2H). 75 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.18-7.29 (m, 2H), 7.13-7.16 (m, 1H), 7.00-7.04(m, 1H), 5.01 (q, J = 7.0 Hz, 1H), 4.64 (dd, J = 12.5, 1.0 Hz, 1H), 4.48 (d, J = 12.5 Hz, 1H), 4.41 (s, 2H), 1.69 (d, J = 7.0 Hz, 3H). 76 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.32-7.41 (m, 2H), 7.26-7.35 (m, 2H), 5.00 (q, J = 7.0 Hz, 1H), 4.66 (d, J = 12.5 Hz, 1H), 4.42 (s, 2H), 4.25-4.32 (m, 1H), 1.69 (d, J = 7.0 Hz, 3H). 77 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.54-7.61 (m, 2H), 7.27-7.34 (m, 2H), 5.94-6.03 (m, 1H), 4.58 (q, J = 7.0 Hz, 1H), 4.42 (s, 2H), 1.66 (d, J = 7.0 Hz, 3H), 1.53 (d, J = 7.0 Hz, 3H). 78 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.83 (dt, J = 7.5, 2.0 Hz, 1H), 7.75 (s, 1H), 7.40-7.43 (m, 1H), 7.09 (t, J = 7.5 Hz, 1H), 5.95 (dt, J = 12.5, 1.0 Hz, 1H), 4.66 (q, J = 7.0 Hz, 1H), 4.51 (d, J = 12.5 Hz, 1H), 4.44 (s, 2H), 1.62 (d, J = 7.0 Hz, 3H). 79 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.00-7.15 (m, 3H), 5.46 (d, J = 12.5 Hz, 1H), 4.93 (dd, J = 12.5, 1.0 Hz, 1H), 4.72 (q, J = 7.0 Hz, 1H), 4.41 (s, 2H), 1.62 (d, J = 7.0 Hz, 3H). 80 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.34 (m, 2H), 7.18-7.20 (m, 1H), 5.61 (d, J = 12.5 Hz, 1H), 4.99 (dd, J = 12.5, 1.0 Hz, 1H), 4.72 (q, J = 7.0 Hz, 1H), 4.44 (s, 2H), 1.61 (d, J =7.0 Hz, 3H). 81 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.07-7.17 (m, 2H), 6.80-6.87 (m, 1H), 4.87-4.90 (m, 2H), 4.38- 4.45 (m, 1H), 4.41 (s, 2H), 1.50 (d, J = 7.0 Hz, 3H). 82 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.65-7.71 (m, 1H), 7.51-7.54 (m, 1H), 7.10-7.13 (m, 1H), 5.91 (dd, J = 12.5, 1.0 Hz, 1H), 4.58-4.70 (m, 2H), 4.43 (s, 2H), 1.56 (d, J = 7.0 Hz, 3H). 83 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.05-7.11 (m, 1H), 6.80-6.84 (m, 1H), 5.31 (d, J = 12.5 Hz, 1H), 5.21 (d, J = 12.5 Hz, 1H), 4.72 (q, J = 7.0 Hz, 1H), 4.44 (s, 2H), 1.62 (d, J = 7.0 Hz, 3H). 84 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.18-7.22 (m, 1H), 6.80-6.84 (m, 1H), 6.50-6.52 (m, 1H), 5.01 (q, J = 7.0 Hz, 1H), 4.39 (s, 2H), 4.27-4.37 (m,2H), 3.80 (s, 3H), 1.70 (d, J =7.0 Hz, 3H). 85 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.17 (d, J = 7.5 Hz, 1H), 6.98-7.01 (m, 1H), 5.86 (dd, J = 12.5, 1.0 Hz, 1H), 4.64-4.75 (m, 2H), 4.38 (s, 2H), 3.87 (s, 3H), 1.62 (d, J = 7.0 Hz, 3H). 86 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.36-8.38 (m, 1H), 8.18-8.21 (m, 1H), 7.29-7.33 (m, 1H), 5.43 (d, J = 1.5 Hz, 2H), 4.61 (q, J = 7.0 Hz, 1H), 4.42 (s, 2H), 1.69 (d, J = 7.0 Hz, 3H). 87 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.93-8.01 (m, 2H), 7.57-7.54 (m, 1H), 7.18 (t, J = 7.5 Hz, 1H), 4.81 (dd, J = 12.5, 1.0 Hz, 1H), 4.74 (q, J = 7.0 Hz, 1H), 4.43-4.46 (m, 3H), 1.72 (d, J = 7.0 Hz, 3H). 89 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.13-7.16 (m, 1H), 7.03-7.10 (m, 1H), 6.72-4.74 (m, 2H), 4.91 (q, J = 7.0 Hz, 1H), 4.69 (s, 2H), 4.42 (s, 2H), 4.28 (dt, J = 12.5, 1.0 Hz, 1H), 1.70 (d, J = 7.0 Hz, 3H). 90 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.09 (t, J = 7.5 Hz, 1H), 6.76-6.796 (m, 1H), 6.63 (dt, J = 7.5, 2.0 Hz, 1H), 6.15-6.16 (m, 1H), 5.30 (dt, J = 12.5, 1.0 Hz, 1H), 4.99 (dt, J = 12.5, 1.0 Hz, 1H), 4.73 (q, J = 7.0 Hz, 1H), 4.50 (s, 2H), 4.30 (s, 2H), 1.62 (d, J = 7.0 Hz, 3H). 91 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.77-7.84 (m, 2H), 7.65-7.72 (m, 2H), 5.82 (d, J = 12.5 Hz, 1H), 4.57-4.66 (m, 2H), 4.43 (s, 2H), 1.58 (d, J = 7.0 Hz, 3H). 92 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.39-7.41 (m, 2H), 7.21-7.29 (m, 1H), 7.19-7.25 (m, 1H), 5.31 (d, J = 12.5 Hz, 1H), 5.11 (dt, J = 12.5, 1.0 Hz, 1H), 4.55 (q, J = 7.0 Hz, 1H), 4.42 (s, 2H), 2.50 (s, 3H), 1.67 (d, J = 7.0 Hz, 3H). 93 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.02-7.09 (m, 2H), 6.59-6.65 (m, 2H), 5.86 (dt, J = 12.5, 1.0 Hz, 1H), 4.69 (q, J = 7.0 Hz, 1H), 4.50 (d, J = 12.5 Hz, 1H), 4.38 (s, 2H), 3.02 (s, 6H), 1.64 (d, J = 7.0 Hz, 3H). 94 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.24-7.33 (m, 4H), 5.01 (q, J = 7.0 Hz, 1H), 4.65 (dd, J = 12.5, 1.0 Hz, 1H), 4.36-4.44 (m, 3H), 1.69 (d, J = 7.0 Hz, 3H). 95 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.22-7.28 (m, 2H), 7.02-7.09 (m, 2H), 4.88-4.98 (m, 2H), 4.78- 4.85 (m, 1H), 4.73 (d, J = 12.5 Hz, 1H), 4.41 (s, 2H), 4.32 (d, J = 12.5 Hz, 1H), 2.84-2.91 (m, 1H), 2.79- 2.86 (m, 1H), 1.45 (d, J = 7.0 Hz, 3H). 96 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.29 (t, J = 7.5 Hz, 1H), 7.05-7.11 (m, 1H), 6.96 (dt, J = 7.5, 2.0 Hz, 1H), 6.59-6.61 (m, 1H), 5.23-5.30 (m, 1H), 4.91-5.10(m, 3H), 4.73 (q, J =7.0 Hz, 1H), 4.52 (s, 2H), 1.62 (d, J = 7.0 Hz, 3H). 97 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.50-7.58 (m, 3H), 7.24-7.31 (m, 2H), 4.93 (q, J = 7.0 Hz, 1H), 4.78 (dt, J = 12.5, 1.0 Hz, 1H), 4.39 (s, 2H), 4.32 (d, J = 12.5 Hz, 1H), 2.10 (s, 3H), 1.65 (d, J = 7.0 Hz, 3H). 98 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.84-7.90 (m, 2H), 7.45-7.51 (m, 2H), 6.01 (dd, J = 12.5, 1.0 Hz, 1H), 4.62-4.72 (m, 2H), 4.45 (s, 2H), 3.95 (s, 3H), 1.65 (d, J = 7.0 Hz, 3H). 99 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.40-7.46 (m, 2H), 6.92-6.98(m, 2H), 5.83 (d, J = 12.5 Hz, 1H), 4.65 (q, J = 7.0 Hz, 1H), 4.41-4.48 (m, 1H), 4.43 (s, 2H), 2.29 (s, 3H), 1.54 (d, J = 7.0 Hz, 3H). 100 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.41-7.52 (m, 4H), 5.95-6.03(m, 1H), 4.51-4.63 (m, 2H), 4.42 (s, 2H), 4.34 (dt, J = 12.5, 1.0 Hz, 1H), 3.44-3.49 (m, 2H), 1.66 (d, J =7.0 Hz, 3H), 1.53 (d, J =7.0 Hz, 3H), 1.18 (t, J = 8.0 Hz, 3H). 101 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.35-7.45 (m, 4H), 5.86 (dt, J = 12.5, 1.0 Hz, 1H), 5.66 (s, 2H), 5.29 (s, 2H), 4.62-4.71 (m, 2H), 3.70-3.77 (m, 1H), 3.55 (dt, J = 12.5, 1.0 Hz, 1H), 1.62 (d, J =7.0 Hz, 3H). 102 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.47-7.54 (m, 2H), 7.18-7.25 (m, 2H), 5.84 (d, J = 12.5 Hz, 1H), 4.67 (q, J = 7.0 Hz, 1H), 4.40-4.49 (m, 3H), 3.45 (q, J = 7.0 Hz, 1H), 2.41 (qt, J = 7.0, 1.0 Hz, 1H), 1.45- 1.56 (m, 4H), 1.27-1.31 (m, 1H). 103 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.34 (m, 4H), 5.04 (q, J = 7.0 Hz, 1H), 4.97 (s, 2H), 4.72 (d, J = 12.5 Hz, 1H), 4.31 (d, J = 12.5 Hz, 1H), 4.17 (d, J = 12.5 Hz, 1H), 3.19 (d, J = 12.5 Hz, 1H), 2.70-2.77 (m, 1H), 2.28-2.36 (m, 1H), 1.63 (d, J =7.0 Hz, 3H), 1.21 (t, J = 8.0 Hz, 3H). 104 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.78-7.84 (m, 2H), 7.31-7.37 (m, 2H), 5.01 (q, J = 7.0 Hz, 1H), 4.40 (s, 2H), 3.63-3.69 (m, 1H), 3.31-3.37 (m, 1H), 3.18-3.24 (m, 1H), 3.10-3.15 (m, 1H), 2.51 (s, 3H), 1.68 (d, J = 7.0 Hz, 3H). 105 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.84-7.90 (m, 2H), 7.59-7.66 (m, 2H), 5.28 (d, J = 12.5 Hz, 1H), 5.18-5.25 (m, 1H), 4.55 (q, J = 7.0 Hz, 1H), 4.42 (s, 2H), 3.30 (s, 3H), 1.67 (d, J = 7.0 Hz, 3H). 106 .sup.1H NMR (500 MHz, Chloroform-d) 6 7.73-7.82 (m, 2H), 7.35-7.41 (m, 2H), 5.00 (q, J = 7.0 Hz, 1H), 4.50 (s, 2H), 3.81-3.99 (m, 4H), 3.63-3.73 (m, 2H), 3.51-3.54 (m, 1H), 1.68 (d, J = 7.0 Hz, 3H), 1.20 (t, J = 6.0 Hz, 6H). 107 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.11-8.13 (m, 1H), 7.33 (t, J = 7.5 Hz, 1H), 7.08-7.10 (m, 1H), 6.94-7.01 (m, 1H), 6.53 (s, 1H), 4.59-4.71 (m, 2H), 4.48-4.54 (m, 1H), 4.44 (s, 2H), 3.67 (s, 3H), 2.52- 2.62 (m, 1H), 2.32-2.42 (m, 1H), 1.63 (d, J = 7.0 Hz, 3H). 108 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.21-7.30 (m, 2H), 7.10-7.16 (m, 1H), 7.00 (s, 1H), 6.75-6.77(m, 1H), 5.63 (dt, J = 12.5, 1.0 Hz, 1H), 4.88 (dt, J = 12.5, 1.0 Hz, 1H), 4.56 (q, J = 7.0 Hz, 1H), 4.41 (s, 2H), 2.99 (s, 3H), 1.63 (d, J = 7.0 Hz, 3H). 109 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.14-8.16 (m, 1H), 7.34 (t, J = 7.5 Hz, 1H), 7.21-7.27 (m, 2H), 6.70 (s, 1H), 4.94 (q, J = 7.0 Hz, 1H), 4.55-4.66 (m, 3H), 4.43 (s, 2H), 4.31-4.38 (m, 1H), 1.70 (d, J =7.0 Hz, 3H), 1.26 (t, J = 8.0 Hz, 3H). 110 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.26 (t, J = 7.5 Hz, 1H), 6.96-6.98 (m, 1H), 6.77-6.769 (m, 1H), 6.30 (dd, J = 12.5, 1.5 Hz, 1H), 5.34 (d, J = 12.5 Hz, 1H), 4.98 (d, J = 12.5 Hz, 1H), 4.67 (q, J = 7.0 Hz, 1H), 4.38 (s, 2H), 4.09 (dt, J = 12.5, 1.0 Hz, 1H), 3.27 (s, 3H), 2.14-2.18 (m, 3H), 1.62 (d, J = 7.0 Hz, 3H). 111 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.97 (t, J = 2.0 Hz, 1H), 7.72 (q, J =2.0 Hz, 1H), 7.43-7.44 (m, 1H), 5.59 (dd, J = 12.5, 1.0 Hz, 1H), 4.96 (dt, J = 12.5, 1.0 Hz, 1H), 4.68 (q, J = 7.0 Hz, 1H), 4.45 (s, 2H), 1.63 (d, J = 7.0 Hz, 3H). 113 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.52-7.62 (m, 4H), 7.38-7.48 (m, 4H), 7.31-7.35 (m, 1H), 4.98 (q, J = 7.0 Hz, 1H), 4.79 (d, J = 12.5 Hz, 1H), 4.37-4.47 (m, 3H), 1.49 (d, J = 7.0 Hz, 3H). 114 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.32-7.36 (m, 3H), 7.24-7.27(m, 1H), 7.10-7.14 (m, 1H), 6.96-7.02 (m, 2H), 6.91-6.93 (m, 1H), 6.64 (s, 1H), 5.65 (dt, J = 12.5, 1.0 Hz, 1H), 4.94 (dt, J = 12.5, 1.0 Hz, 1H), 4.71 (q, J = 7.0 Hz, 1H), 4.03 (s, 2H), 1.63 (d, J = 7.0 Hz, 3H). 115 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.73 (s, 1H), 8.63 (dd, J = 5.0, 1.0 Hz, 1H), 7.75-7.84 (m, 2H), 7.61-7.63 (m, 1H), 7.43-7.51 (m, 2H), 7.37-7.39 (m, 1H), 6.01 (d, J = 12.5 Hz, 1H), 4.72 (q, J = 7.0 Hz, 1H), 4.60 (d, J = 12.5 Hz, 1H), 4.43 (s, 2H), 1.65 (d, J = 7.0 Hz, 3H). 116 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.48-8.50 (m, 1H), 8.36 (s, 1H), 7.52-7.54(m,1H), 7.44-7.47 (m,1H), 5.81 (d, J = 12.5 Hz, 2H), 4.41-4.48 (m, 2H), 4.42 (s, 4H), 1.70 (d, J = 7.0 Hz, 5H). 117 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.45 (d, J = 5.0 Hz, 2H), 7.34 (d, J = 5.0 Hz, 2H), 5.87 (d, J = 12.5 Hz, 1H), 4.67 (q, J = 7.0 Hz, 1H), 4.46 (d, J = 12.5 Hz, 1H), 4.40 (s, 2H), 1.63 (d, J = 7.0 Hz, 3H). 118 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.42 (d, J = 5.0 Hz, 1H), 7.21 (d, J = 1.0 Hz, 1H), 7.13-7.18 (m, 1H), 5.00 (q, J = 7.0 Hz, 1H), 4.58 (d, J = 12.5 Hz, 1H), 4.41 (s, 2H), 4.26 (d, J = 12.5 Hz, 1H), 2.59 (s, 3H), 1.68 (d, J = 7.0 Hz, 3H). 119 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.35 (s, 1H), 8.27 (d, J = 5.0 Hz, 1H), 7.23 (d, J = 5.0 Hz, 1H), 5.01 (q, J = 7.0 Hz, 1H), 4.40 (s, 2H), 3.46-3.66 (m, 3H), 2.83 (td, J = 12.0, 3.0 Hz, 1H), 1.68 (d, J = 7.0 Hz, 3H). 120 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.49-8.50 (m, 1H), 7.51-7.59 (m, 2H), 7.31-7.34 (m, 1H), 5.67 (d, J = 12.5 Hz, 1H), 4.87 (d, J = 12.5 Hz, 1H), 4.45 (q, J = 7.0 Hz, 1H), 4.41 (s, 2H), 1.71 (d, J = 7.0 Hz, 3H). 121 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.69 (d, J = 2.0 Hz, 1H), 8.62 (d, J = 7.5 Hz, 1H), 8.30 (d, J = 7.5 Hz, 1H), 5.57 (dd, J = 12.5, 2.0 Hz, 1H), 5.23 (d, J = 12.5 Hz, 1H), 4.51 (q, J = 7.0 Hz, 1H), 4.42 (s, 2H), 1.75 (d, J = 7.0 Hz, 3H). 122 .sup.1H NMR (500 MHz, Chloroform-d) ? 9.32-9.39 (m, 1H), 7.67-7.74 (m, 2H), 5.63 (d, J = 12.5 Hz, 1H), 4.94 (d, J = 12.5 Hz, 1H), 4.63 (q, J = 7.0 Hz, 1H), 4.42 (s, 2H), 1.63 (d, J = 7.0 Hz, 3H). 123 .sup.1H NMR (500 MHz, Chloroform-d) ? 9.44 (d, J = 1.5 Hz, 1H), 9.26 (d, J = 7.5 Hz, 1H), 7.60 (dd, J = 7.5, 1.5 Hz, 1H), 4.97 (q, J = 7.0 Hz, 1H), 4.64 (d, J = 12.5 Hz, 1H), 4.41 (s, 2H), 4.30 (d, J = 12.5 Hz, 1H), 1.69 (d, J = 7.0 Hz, 3H). 124 .sup.1H NMR (500 MHz, Chloroform-d) ? 9.12 (s, 1H), 8.78 (s, 2H), 5.61 (d, J = 12.5 Hz, 1H), 4.63 (q, J = 7.0 Hz, 1H), 4.43 (d, J = 12.5 Hz, 1H), 4.42 (s, 2H), 1.58 (d, J = 7.0 Hz, 3H). 125 .sup.1H NMR (500 MHz, Chloroform-d) ? 9.39 (d, J = 1.5 Hz, 1H), 8.71 (d, J = 5.0 Hz, 1H), 7.32 (dd, J = 5.0, 1.5 Hz, 1H), 4.99 (q, J = 7.0 Hz, 1H), 4.40 (s, 2H), 3.76-3.81 (m, 1H), 3.59-3.64 (m, 1H), 3.41-3.47 (m, 1H), 2.98-3.03 (m, 1H), 1.69 (d, J = 7.0 Hz, 3H). 126 .sup.1H NMR (500 MHz, Chloroform-d) ? 9.18 (s, 2H), 5.87 (d, J = 12.5 Hz, 1H), 5.44 (d, J = 12.5 Hz, 1H), 4.71 (q, J = 7.0 Hz, 1H), 4.45 (s, 2H), 1.63 (d, J = 7.0 Hz, 3H). 127 .sup.1H NMR (500 MHz, Chloroform-d) ? 5.93 (d, J = 1.5 Hz, 1H), 5.41 (dd, J = 12.5, 1.5 Hz, 1H), 5.28 (d, J = 12.5 Hz, 1H), 4.68 (q, J = 7.0 Hz, 1H), 4.47 (s, 2H), 3.60 (s, 3H), 2.21 (s, 3H), 1.63 (d, J = 7.0 Hz, 3H). 128 .sup.1H NMR (500 MHz, Chloroform-d) ? 5.80 (s, 1H), 4.66 (q, J =7.0 Hz, 1H), 4.13 (d, J = 16 Hz, 2H), 3.85 (s, 2H), 3.80 (s, 3H), 1.84-1.90 (m, 1H), 1.73 (d, J =7.0 Hz, 3H), 0.83-0.92 (m, 2H), 0.66-0.70 (m, 2H). 129 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.47 (s, 1H), 6.66 (d, J = 1.0 Hz, 1H), 5.80 (dd, J = 12.5, 1.0 Hz, 1H), 4.76 (d, J = 12.5 Hz, 1H), 4.68 (q, J = 7.0 Hz, 1H), 4.46 (s, 2H), 3.54 (s, 3H), 1.64 (d, J = 7.0 Hz, 3H). 130 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.12 (d, J = 7.5 Hz, 1H), 6.62 (d, J = 7.5 Hz, 1H), 6.19 (d, J = 12.5 Hz, 1H), 4.62-4.72 (m, 2H), 4.47 (s, 2H), 3.56 (s, 3H), 1.65 (d, J = 7.0 Hz, 3H). 131 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.54 (s, 1H), 6.83 (d, J = 1.0 Hz, 1H), 5.64 (d, J = 12.5 Hz, 1H), 4.82 (dd, J = 12.5, 1.0 Hz, 1H), 4.73 (q, J = 7.0 Hz, 1H), 4.50 (s, 2H), 3.57 (s, 3H), 1.64 (d, J =7.0 Hz, 3H). 132 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.39 (d, J = 7.5 Hz, 1H), 6.09 (d, J = 7.5 Hz, 1H), 5.03 (q, J = 7.0 Hz, 1H), 4.59 (d, J = 12.5 Hz, 1H), 4.52 (d, J = 12.5 Hz, 1H), 4.44 (s, 2H), 3.91 (s, 3H), 1.70 (d, J = 7.0 Hz, 3H). 133 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.16 (d, J = 1.5 Hz, 1H), 6.73 (d, J = 1.5 Hz, 1H), 4.80-4.85 (m, 1H), 4.67-4.71 (m, 1H), 4.46 (s, 2H), 4.32-4.38 (m, 1H), 4.17-4.26 (m, 2H), 2.39-2.44 (m, 1H), 2.08-2.14 (m, 1H), 1.57-1.72 (m, 5H), 0.95 (t, J = 8.0 Hz, 3H). 134 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.47 (s, 1H), 4.92-5.04 (m, 2H), 4.39-4.47 (m, 3H), 3.58 (s, 3H), 1.74 (d, J = 7.0 Hz, 3H). 135 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.49 (d, J = 2.5 Hz, 1H), 5.04-5.09(m, 1H), 4.70 (q, J = 7.0 Hz, 1H), 4.50 (s, 2H), 3.92-3.96 (m, 1H), 2.97-3.03 (m, 1H), 2.89-2.93 (m, 1H), 1.63 (d, J = 7.0 Hz, 3H). 136 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.33 (s, 1H), 8.09 (s, 1H), 6.78-6.89(m, 2H), 4.58 (q, J =7.0 Hz, 1H), 4.45 (s, 2H), 1.69 (d, J = 7.0 Hz, 3H). 137 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.80 (d, J = 7.5 Hz, 1H), 7.62 (d, J = 7.5 Hz, 1H), 6.16 (d, J = 12.5 Hz, 1H), 5.88 (d, J = 12.5 Hz, 1H), 5.03 (q, J = 7.0 Hz, 1H), 4.44 (s, 2H), 1.72 (d, J = 7.0 Hz, 3H). 138 .sup.1H NMR (500 MHz, Chloroform-d) ? 5.63 (d, J = 12.5 Hz, 1H), 5.41 (d, J = 12.5 Hz, 1H), 4.61 (q, J = 7.0 Hz, 1H), 4.46 (s, 2H), 3.89 (s, 3H), 1.69 (d, J = 7.0 Hz, 3H). 139 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.32 (dd, J = 7.5, 1.5 Hz, 1H), 6.33 (t, J = 7.5 Hz, 1H), 6.12 (dd, J = 7.5, 1.5 Hz, 1H), 5.02 (q, J = 7.0 Hz, 1H), 4.78 (d, J = 12.5 Hz, 1H), 4.45 (s, 2H), 4.40 (d, J = 12.5 Hz, 1H), 1.74 (d, J = 7.0 Hz, 3H). 140 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.39 (d, J = 7.5 Hz, 1H), 7.11 (d, J = 1.5 Hz, 1H), 6.24 (dd, J = 7.5, 1.5 Hz, 1H), 4.63-4.73 (m, 2H), 4.61 (td, J = 12.0, 3.5 Hz, 1H), 4.47 (s, 2H), 2.70 (td, J = 12.0, 3.5 Hz, 1H), 2.37 (td, J = 12.0, 3.4 Hz, 1H), 1.65 (d, J = 7.0 Hz, 3H). 141 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.93 (s, 1H), 6.89 (d, J = 1.5 Hz, 1H), 5.91 (d, J = 12.5 Hz, 1H), 4.82 (dd, J = 12.5, 1.5 Hz, 1H), 4.72 (q, J = 7.0 Hz, 1H), 4.50 (s, 2H), 1.64 (d, J = 7.0 Hz, 3H). 142 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.04 (d, J = 1.5 Hz, 1H), 7.59-7.64 (m, 1H), 5.02 (q, J = 7.0 Hz, 1H), 4.45 (s, 2H), 4.00-4.12 (m, 2H), 3.57-3.60 (m, 1H), 2.97-3.04 (m, 1H), 1.72 (d, J = 7.0 Hz, 3H). 143 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.55 (d, J = 7.5 Hz, 1H), 7.16 (d, J = 7.5 Hz, 1H), 5.95 (d, J = 12.5 Hz, 1H), 4.94 (d, J = 12.5 Hz, 1H), 4.72 (q, J = 7.0 Hz, 1H), 4.51 (s, 2H), 1.64 (d, J = 7.0 Hz, 3H). 144 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.10 (d, J = 7.5 Hz, 1H), 6.41 (dd, J = 7.5, 1.0 Hz, 1H), 5.93 (d, J = 12.5 Hz, 1H), 5.09 (dd, J = 12.5, 1.0 Hz, 1H), 4.72 (q, J = 7.0 Hz, 1H), 4.48 (s, 2H), 1.64 (d, J = 7.0 Hz, 3H). 145 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.24 (d, J = 7.5 Hz, 1H), 6.45 (dd, J = 7.5, 1.0 Hz, 1H), 4.98-5.06 (m, 2H), 4.67 (d, J = 12.5 Hz, 1H), 4.44 (s, 2H), 1.71 (d, J =7.0 Hz, 3H). 146 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.12 (d, J = 1.5 Hz, 1H), 8.07 (d, J = 1.5 Hz, 1H), 6.06 (d, J = 12.5 Hz, 1H), 4.63-4.72 (m, 2H), 4.47 (s, 2H), 1.68 (d, J = 7.0 Hz, 3H). 147 .sup.1H NMR (500 MHz, Chloroform-d) & 6.03-6.07 (m, 1H), 4.72 (q, J = 7.0 Hz, 1H), 4.61-4.69(m, 1H), 4.48 (s, 2H), 2.42-2.46 (m, 6H), 1.65 (d, J = 7.0 Hz, 3H). 148 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.60 (s, 1H), 4.57-4.68( m, 2H), 4.45 (s, 2H), 4.14-4.20 (m, 1H), 2.48-2.53 (m, 1H), 1.83-1.88 (m, 1H), 1.69 (d, J = 7.0 Hz, 3H). 149 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.60 (s, 1H), 5.01 (q, J = 7.0 Hz, 1H), 4.43 (s, 2H), 4.33 (d, J = 12.5 Hz, 1H), 4.13 (d, J = 12.5 Hz, 1H), 1.70 (d, J = 7.0 Hz, 3H). 150 .sup.1H NMR (500 MHz, Chloroform-d) ? 5.06 (q, J = 7.0 Hz, 1H), 4.59 (q, J = 7.0 Hz, 1H), 4.44 (s, 2H), 1.69 (d, J = 7.0 Hz, 3H), 1.61 (d, J = 7.0 Hz, 3H). 151 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.01 (s, 1H), 5.45 (d, J = 12.5 Hz, 1H), 4.62 (q, J = 7.0 Hz, 1H), 4.51 (d, J = 12.0 Hz, 1H), 4.45 (s, 2H), 1.64 (d, J = 7.0 Hz, 3H). 152 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.83 (d, J = 1.0 Hz, 1H), 5.01 (q, J = 7.0 Hz, 1H), 4.43 (s, 2H), 3.79 (dt, J = 12.5, 3.0 Hz, 1H), 3.43-3.51 (m, 1H), 3.25 (td, J = 12.5, 2.0 Hz, 1H), 3.09 (td, J = 12.5, 3.0 Hz, 1H), 1.70 (d, J = 7.0 Hz, 3H). 153 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.19 (s, 1H), 5.41 (d, J = 12.5 Hz, 1H), 4.67 (d, J = 12.5 Hz, 1H), 4.56 (q, J = 7.0 Hz, 1H), 4.44 (s, 2H), 1.67 (d, J = 7.0 Hz, 3H). 154 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.13 (dd, J = 7.5, 1.5 Hz, 1H), 6.96 (t, J = 7.5 Hz, 1H), 6.77 (dt, J = 7.5, 1.0 Hz, 1H), 5.03 (q, J = 7.0 Hz, 1H), 4.84 (d, J = 12.5 Hz, 1H), 4.67 (d, J = 12.5 Hz, 1H), 4.45 (s, 2H), 1.71 (d, J = 7.0 Hz, 3H). 155 .sup.1H NMR (500 MHz, Chloroform-d) ? 6.23-6.30 (m, 1H), 4.69 (q, J = 7.0 Hz, 1H), 4.41-4.49 (m, 3H), 2.35-2.41 (m, 6H), 2.29 (d, J = 1.0 Hz, 3H), 1.62 (d, J = 7.0 Hz, 3H). 156 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.63 (d, J = 7.5 Hz, 1H), 7.21 (d, J = 7.5 Hz, 1H), 5.09 (d, J = 12.5 Hz, 1H), 5.03 (q, J =7.0 Hz, 1H), 4.61 (d, J = 12.5 Hz, 1H), 4.44 (s, 2H), 1.78 (d, J =7.0 Hz, 3H). 157 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.72 (s, 1H), 5.56 (d, J = 12.5 Hz, 1H), 5.36 (d, J = 12.5 Hz, 1H), 4.61 (q, J = 7.0 Hz, 1H), 4.45 (s, 2H), 2.80 (s, 3H), 1.71 (d, J =7.0 Hz, 3H). 158 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.88 (s, 1H), 7.66-7.67 (m, 1H), 5.76 (dd, J = 12.5, 1.0 Hz, 1H), 5.02 (d, J = 12.5 Hz, 1H), 4.73 (q, J = 7.0 Hz, 1H), 4.49 (s, 2H), 1.64 (d, J = 7.0 Hz, 3H). 159 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.74 (s, 1H), 7.79 (s, 1H), 4.99-5.08 (m, 2H), 4.47 (d, J = 12.5 Hz, 1H), 4.45 (s, 2H), 1.71 (d, J = 7.0 Hz, 3H). 160 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.85 (d, J = 7.5 Hz, 1H), 7.06 (d, J = 7.5 Hz, 1H), 5.47 (d, J = 12.5 Hz, 1H), 5.12 (d, J = 12.5 Hz, 1H), 4.61 (q, J =7.0 Hz, 1H), 4.45 (s, 2H), 1.70 (d, J = 7.0 Hz, 3H). 161 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.72 (d, J = 7.5 Hz, 1H), 7.08 (dd, J = 7.5, 1.0 Hz, 1H), 5.03 (q, J = 7.0 Hz, 1H), 4.53-4.59 (m, 1H), 4.44 (s, 2H), 4.27 (d, J = 12.5 Hz, 1H), 1.71 (d, J = 7.0 Hz, 3H). 162 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.72 (t, J = 1.5 Hz, 1H), 7.78 (t, J = 1.5 Hz, 1H), 5.09-5.14 (m, 1H), 4.61 (q, J = 7.0 Hz, 1H), 4.44 (s, 2H), 4.26-4.30 (m, 1H), 2.93-2.98 (m, 1H), 2.55-2.59 (m, 1H), 1.68 (d, J = 7.0 Hz, 3H). 163 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 7.72 (d, J = 7.5 Hz, 1H), 7.54 (d, J = 7.5 Hz, 1H), 6.81 (s, 2H), 5.80 (d, J = 12.5 Hz, 1H), 5.50 (d, J = 12.5 Hz, 1H), 4.69 (q, J = 7.0 Hz, 1H), 1.53 (d, J = 7.0 Hz, 3H). 164 .sup.1H NMR (500 MHz, Chloroform-d) ? 9.07 (s, 1H), 5.63 (d, J = 12.5 Hz, 1H), 4.70 (q, J = 7.0 Hz, 1H), 4.58 (d, J = 12.5 Hz, 1H), 4.46 (s, 2H), 1.63 (d, J =7.0 Hz, 3H). 165 .sup.1H NMR (500 MHz, Chloroform-d) ? 5.00 (q, J = 7.0 Hz, 1H), 4.44 (s, 2H), 3.64-3.67 (m, 1H), 3.26-3.31 (m, 1H), 3.07-3.10 (m, 1H), 2.73-2.79 (mz, 1H), 1.69 (d, J = 7.0 Hz, 3H). 166 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.01 (d, J = 1.0 Hz, 1H), 4.79 (d, J = 12.5 Hz, 1H), 4.64-4.70 (m, 1H), 4.55 (q, J = 7.0 Hz, 1H), 4.45 (s, 2H), 1.68 (d, J = 7.0 Hz, 3H). 167 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.02 (s, 1H), 5.62 (d, J = 12.5 Hz, 1H), 4.57-4.68 (m, 2H), 4.45 (s, 2H), 1.64 (d, J = 7.0 Hz, 3H). 168 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.19 (d, J =1.0 Hz, 1H), 5.01 (q, J = 7.0 Hz, 1H), 4.44 (s, 2H), 4.18 (d, J = 12.5 Hz, 1H), 4.01 (dd, J = 12.5, 1.0 Hz, 1H), 1.68 (d, J = 7.0 Hz, 3H). 169 .sup.1H NMR (500 MHz, Chloroform-d) ? 6.15-6.20 (m, 2H), 5.94-6.00 (m, 1H), 5.75 (dd, J = 11.0, 6.0 Hz, 1H), 5.05-5.12 (m, 1H), 4.89-5.00 (m, 1H), 4.67 (q, J =7.0 Hz, 1H), 4.44 (s, 2H), 4.34-4.36 (m, 1H), 3.92-4.02 (m, 2H), 1.56-1.65 (m, 4H). 170 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.57-7.61 (m, 2H), 7.13-7.17 (m, 2H), 5.12 (d, J = 12.5 Hz, 1H), 5.00 (q, J = 7.0 Hz, 1H), 4.34-4.43 (m, 3H), 1.74 (d, J = 7.0 Hz, 3H). 171 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.77 (d, J = 1.5 Hz, 1H), 7.42 (d, J = 7.5 Hz, 1H), 7.06-7.14 (m, 2H), 6.63-6.65 (m, 1H), 6.05 (d, J = 12.5 Hz, 1H), 4.65-4.73 (m, 2H), 4.43 (s, 2H), 3.74 (s, 3H), 1.65 (d, J = 7.0 Hz, 3H). 172 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.39 (s, 1H), 7.71 (d, J = 1.5 Hz, 1H), 7.50 (dd, J = 7.5, 1.5 Hz, 1H), 7.25 (d, J = 7.5 Hz, 1H), 5.90 (d, J = 12.5 Hz, 1H), 4.58-4.69 (m, 2H), 4.43 (s, 2H), 4.36 (dq, J = 12.5, 8.0 Hz, 1H), 4.14 (dq, J = 12.5, 8.0 Hz, 1H), 1.63 (t, J = 8.0 Hz, 3H), 1.57 (d, J = 7.0 Hz, 3H). 173 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.56-7.58 (m, 1H), 7.48-7.50 (m, 1H), 7.26-7.30 (m, 1H), 7.20-7.24 (m, 1H), 6.59 (d, J = 2.0 Hz, 1H), 5.90 (d, J = 12.5 Hz, 1H), 5.17 (dd, J = 12.5, 1.0 Hz, 1H), 4.72 (q, J = 7.0 Hz, 1H), 4.12 (s, 2H), 1.64 (d, J = 7.0 Hz, 3H). 174 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.24 (s, 1H), 7.43-7.49 (m, 2H), 7.29 (dd, J = 7.5, 1.5 Hz, 1H), 5.01 (q, J = 7.0 Hz, 1H), 4.75 (d, J = 12.5 Hz, 1H), 4.42 (s, 2H), 4.42 (d, J = 12.5 Hz, 1H), 1.70 (d, J = 7.0 Hz, 3H). 175 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.67 (d, J = 7.5 Hz, 1H), 7.48 (d, J = 1.5 Hz, 1H), 7.40 (dd, J = 7.5, 1.5 Hz, 1H), 6.15 (d, J = 12.5 Hz, 1H), 4.64-4.75 (m, 2H), 4.39 (s, 2H), 2.61 (s, 3H), 1.65 (d, J = 7.0 Hz, 3H). 176 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.02-7.04 (m, 1H), 6.85-6.95 (m, 2H), 6.04 (d, J = 5.0 Hz, 1H), 5.98 (d, J = 12.5 Hz, 1H), 5.75 (d, J = 5.0 Hz, 1H), 4.67 (q, J = 7.0 Hz, 1H), 4.52-4.59 (m, 1H), 4.38 (s, 2H), 1.63 (d, J = 7.0 Hz, 3H). 177 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.82-7.85 (m, 2H), 7.26-7.37 (m, 3H), 5.79 (d, J = 12.5 Hz, 1H), 5.65 (d, J = 12.5 Hz, 1H), 4.61 (q, J = 7.0 Hz, 1H), 4.42 (s, 2H), 1.72 (d, J = 7.0 Hz, 3H). 178 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.93 (dt, J = 7.0, 1.5 Hz, 2H), 7.37-7.45 (m, 2H), 6.12 (d, J = 12.5 Hz, 1H), 5.62 (d, J = 12.5 Hz, 1H), 4.61 (q, J = 7.0 Hz, 1H), 4.42 (s, 2H), 1.75 (d, J = 7.0 Hz, 3H). 179 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.86 (dd, J = 7.5, 1.5 Hz, 1H), 7.71 (d, J = 1.5 Hz, 1H), 7.42 (d, J = 7.5 Hz, 1H), 7.32 (dd, J = 7.5, 1.5 Hz, 1H), 7.26 (dd, J = 7.5, 1.5 Hz, 1H), 5.03 (q, J = 7.0 Hz, 1H), 4.46 (s, 2H), 3.61-3.72 (m, 2H), 3.46-3.50 (m, 1H), 3.16-3.21 (m, 1H), 1.66 (d, J = 7.0 Hz, 3H). 180 .sup.1H NMR (500 MHz, Chloroform-d) ? 9.34 (s, 1H), 8.11 (s, 1H), 7.86 (d, J = 7.5 Hz, 1H), 7.46-7.48 (m, 1H), 5.34-5.41 (m, 1H), 5.29 (d, J = 12.5 Hz, 1H), 4.58 (q, J = 7.0 Hz, 1H), 4.43 (s, 2H), 1.69 (d, J = 7.0 Hz, 3H). 181 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.83-7.92 (m, 2H), 7.73-7.81 (m, 2H), 7.52 (dd, J = 7.5, 1.5 Hz, 1H), 7.40-7.49 (m, 2H), 6.13 (d, J = 12.0 Hz, 1H), 4.69-4.77 (m, 2H), 3.34 (s, 2H), 1.65 (d, J = 7.0 Hz, 3H). 182 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.76-7.82 (m, 2H), 7.72 (d, J = 7.5 Hz, 2H), 7.53-7.57 (m, 2H), 5.05 (q, J = 7.0 Hz, 1H), 4.70 (d, J = 12.5 Hz, 1H), 4.44 (d, J = 12.5 Hz, 1H), 3.76 (s, 2H), 1.70 (d, J = 7.0 Hz, 3H). 183 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.87 (dd, J = 7.5, 1.5 Hz, 1H), 7.70 (d, J = 1.5 Hz, 1H), 7.55-7.61 (m, 2H), 7.35 (dt, J = 7.5, 1.0 Hz, 1H), 6.79 (t, J = 1.5 Hz, 1H), 6.09 (dt, J = 12.5, 1.0 Hz, 1H), 4.67-4.76 (m, 2H), 3.87 (s, 3H), 3.45 (s, 2H), 1.66 (d, J = 7.0 Hz, 3H). 184 .sup.1H NMR (500 MHz, Chloroform-d) ? 9.16-9.20 (m, 1H), 8.49 (d, J = 7.5 Hz, 1H), 7.84-7.88 (m, 2H), 7.80 (d, J = 1.5 Hz, 1H), 7.53 (dd, J = 7.5, 1.5 Hz, 1H), 6.12 (dd, J = 12.5, 1.0 Hz, 1H), 4.68-4.76 (m, 2H), 3.45 (s, 2H), 1.65 (d, J = 7.0 Hz, 3H). 185 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.84 (dd, J = 7.5, 1.5 Hz, 1H), 7.97-8.07 (m, 2H), 7.82 (t, J = 1.5 Hz, 1H), 7.63-7.65 (m, 1H), 7.30 (t, J = 7.5 Hz, 1H), 4.97 (q, J =7.0 Hz, 1H), 4.90 (d, J = 12.5 Hz, 1H), 4.47 (dt, J = 12.5, 1.0 Hz, 1H), 3.75 (s, 2H), 1.45 (d, J = 7.0 Hz, 3H). 186 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.78 (s, 2H), 8.07-8.14 (m, 2H), 7.64 (dd, J = 7.5, 1.5 Hz, 1H), 6.11 (d, J = 12.5 Hz, 1H), 4.67-4.78 (m, 2H), 3.47 (s, 2H), 1.65 (d, J =7.0 Hz, 3H). 187 .sup.1H NMR (500 MHz, Chloroform-d) ? 9.93 (d, J = 1.5 Hz, 1H), 9.71 (s, 1H), 7.70-7.80 (m, 2H), 7.64 (dd, J = 7.0, 1.5 Hz, 1H), 4.85 (td, J = 12.0, 1.5 Hz, 1H), 4.58-4.67 (m, 2H), 3.79 (s, 2H), 3.23 (dt, J = 11.0, 1.5 Hz, 1H), 2.71 (td, J = 12.0, 3.5 Hz, 1H), 1.61 (d, J = 7.0 Hz, 3H). 188 .sup.1H NMR (500 MHz, Chloroform-d) ? 9.27 (d, J = 7.5 Hz, 1H), 8.19 (d, J = 7.5 Hz, 1H), 8.03 (dd, J = 7.5, 1.5 Hz, 1H), 7.82 (dd, J = 7.5, 1.5 Hz, 1H), 7.55-7.59 (m, 1H), 5.04 (q, J = 7.0 Hz, 1H), 4.75 (d, J = 12.5 Hz, 1H), 4.45 (d, J = 12.5 Hz, 1H), 3.76 (s, 2H), 1.70 (d, J = 7.0 Hz, 3H). 189 .sup.1H NMR (500 MHz, Chloroform-d) ? 6.89-6.91 (m, 1H), 6.69 (s, 1H), 6.49 (d, J = 7.5 Hz, 1H), 5.83 (d, J = 12.5 Hz, 1H), 4.69 (q, J = 7.0 Hz, 1H), 4.36-4.42 (m, 1H), 4.27 (dt, J = 11.5, 1.5 Hz, 1H), 4.12-4.21 (m, 2H), 4.00-4.06 (m, 1H), 3.76 (s, 2H), 1.63 (d, J =7.0 Hz, 3H). 190 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.27-7.38 (m, 5H), 6.08 (d, J = 12.5 Hz, 1H), 4.67 (q, J = 7.0 Hz, 1H), 4.48 (d, J = 12.5 Hz, 1H), 2.83 (s, 1H), 2.74 (s, 3H), 1.63 (d, J = 7.0 Hz, 3H). 191 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.46-7.53 (m, 2H), 7.26-7.34 (m, 2H), 7.16-7.24 (m, 1H), 4.98 (q, J = 7.0 Hz, 1H), 4.63-4.66 (m, 1H), 4.25-4.28 (m, 1H), 3.80 (dq, J = 12.5, 8.0 Hz, 1H), 3.41 (dq, J = 12.5, 8.0 Hz, 1H), 2.93 (s, 1H), 1.62 (d, J = 7.0 Hz, 3H), 1.21 (t, J = 8.0 Hz, 3H). 192 .sup.1H NMR (500 MHz, Chloroform-d) ? 9.90 (s, 1H), 7.27-7.38 (m, 5H), 5.54 (d, J = 12.5 Hz, 1H), 4.79 (d, J = 12.5 Hz, 1H), 4.57 (q, J =7.0 Hz, 1H), 2.20 (s, 3H), 1.67 (d, J = 7.0 Hz, 3H). 193 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.64 (dd, J = 7.5, 1.5 Hz, 1H), 7.27-7.38 (m, 5H), 6.43 (t, J = 7.5 Hz, 1H), 6.37 (dt, J = 7.5, 1.5 Hz, 1H), 5.98 (d, J = 12.5 Hz, 1H), 5.24-5.32 (m, 2H), 4.66 (q, J = 7.0 Hz, 1H), 4.51-4.61 (m, 2H), 1.64 (d, J = 7.0 Hz, 3H). 194 .sup.1H NMR (500 MHz, Chloroform-d) ? 8.02 (s, 1H), 7.93-7.99 (m, 2H), 7.54 (t, J = 7.5 Hz, 2H), 7.27- 7.38 (m, 6H), 5.91 (d, J = 12.5 Hz, 1H), 4.70 (q, J = 7.0 Hz, 1H), 4.60 (d, J = 12.5 Hz, 1H), 1.65 (d, J = 7.0 Hz, 3H). 195 .sup.1H NMR (500 MHz, Chloroform-d) ? 7.14-7.42 (m, 10H), 6.00 (d, J = 12.5 Hz, 1H), 5.05 (d, J = 12.5 Hz, 1H), 4.69 (q, J = 7.0 Hz, 1H), 4.54 (d, J = 12.5 Hz, 1H), 4.26 (dd, J = 12.5, 1.5 Hz, 1H), 3.63 (s, 1H), 1.65 (d, J = 7.0 Hz, 3H). 196 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 197 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 198 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 199 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 200 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 201 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 202 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 203 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 7.51 (q, J = 1.5 Hz, 1H), 7.36 (s, 2H), 7.35 (qt, J = 5.5, 3.0 Hz, 2H), 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). 204 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 205 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 206 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 207 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 208 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 209 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 210 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 211 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 212 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 7.49 (dd, J = 7.0, 2.0 Hz, 1H), 6.81 (s, 2H), 6.38-6.47 (m, 2H), 5.51 (d, J = 12.5 Hz, 1H), 5.07 (dd, J = 12.5, 1.0 Hz, 1H), 4.69 (q, J = 7.0 Hz, 1H), 1.54 (d, J = 7.0 Hz, 3H). 213 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 214 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 215 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 216 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 217 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 218 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 219 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 220 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 221 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 222 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 223 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 224 .sup.1H NMR (500 MHz, DMSO-d.sub.6) & 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). 225 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 226 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 227 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 228 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 229 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 230 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 231 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 232 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 233 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 234 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 235 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 236 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 237 .sup.1H NMR (500 MHz, DMSO-d.sub.6) ? 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). 238 .sup.1H NMR (500 MHz, Chloroform-d) 5.73 (q, J = 7.0 Hz, 1H), 4.55 (s, 2H), 4.43 (s, 2H), 1.61 (d, J = 7.0 Hz, 3H). 239 .sup.1H NMR (500 MHz, DMSO-d.sub.6) 7.33-7.19 (m, 5H), 7.03(s, 2H), 6.43-6.34 (m, 2H), 6.22 (s, 1H), 4.84 (d, J = 7.0 Hz, 1H), 4.70-4.62 (m, 2H), 1.51 (d, J = 7.0 Hz, 3H).

(5) 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.

(6) 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.

(7) The examples of representative compounds are as follows:

1. Synthesis of Compound 4

(8) (1) Compound 4-1 (300 mg, 2.77 mmol) and TEA (337 mg, 3.33 mmol) were dissolved in dehydrated dichloromethane (20 ml), cooled to 0? C. and compound a (659 mg, 3.05 mmol) was slowly added dropwise. Heated slowly to room temperature and continued to react for 12 hours. The reaction was quenched by pouring the reaction solution into ice water, extracted and the organic phase was washed one time with 50 ml of saturated sodium bicarbonate. The organic phase was dried and then concentrated to obtain compound 4-2 (850 mg, crude product). Without further purification, the compound was directly used in the next step.

(9) ##STR00315## (2) Compound b (400 mg, 2.13 mmol), compound 4-2 (850 mg, crude product) obtained from step (1), 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 hours. After completed reaction of the starting materials according to LC-MS detection, the reaction solution was cooled to room temperature, and extracted with water (50 ml) and MTBE (50 ml). The organic phase was dried, concentrated, and separated by column chromatography to obtain compound 4 (250 mg, yield 41%), as a white solid.

(10) ##STR00316##

2. Synthesis of Compound 41

(11) (1) Compound 41-1 (500 mg, 2.29 mmol), NBS (408 mg, 2.29 mmol), a catalytic amount of AIBN (10 mg) and carbon tetrachloride (20 ml) were added to a 100 ml single mouth flask and agitated for 12 hours at 60? C. After completed reaction of the starting materials according to HPLC detection, the reaction solution was cooled to room temperature. The solid was filtered and the carbon tetrachloride phase was concentrated, to obtain compound 41-2 (680 mg, crude product), Without further purification, the compound was directly used in the next step.

(12) ##STR00317## (2) Compound b (400 mg, 1.70 mmol), compound 41-2 (680 mg, crude product) obtained from step (1), 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 hours. 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 MTBE (50 ml?2). The organic phase was dried, concentrated, and separated by column chromatography to obtain compound 41 (260 mg, yield 37%).

(13) ##STR00318##

3. Synthesis of Compound 67

(14) (1) Compound 67-1 (300 mg, 2.42 mmol) and TEA (293 mg, 2.90 mmol) were dissolved in dehydrated dichloromethane (20 ml), cooled to 0? C. and compound a (573 mg, 2.66 mmol) was slowly added dropwise. Heated slowly to room temperature and continued to react for 12 hours. The reaction was quenched by pouring the reaction solution into ice water, extracted and the organic phase was washed one time with 50 ml of saturated sodium bicarbonate. The organic phase was dried and then concentrated to obtain compound 67-2 (650 mg, crude product). Without further purification, the compound was directly used in the next step.

(15) ##STR00319## (2) Compound b (400 mg, 2.13 mmol), compound 67-2 (650 mg, crude product) obtained from step (1), 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 hours. 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 MTBE (50 ml?2). The organic phase was dried, concentrated, and separated by column chromatography to obtain compound 67 (300 mg, yield 48%), as a white solid.

(16) ##STR00320##

4. Synthesis of Compound 120

(17) (1) Compound 120-1 (300 mg, 2.75 mmol) and TEA (334 mg, 3.30 mmol) were dissolved in dehydrated dichloromethane (20 ml), cooled to 0? C. and compound a (653 mg, 3.02 mmol) was slowly added dropwise. Heated slowly to room temperature and continued to react for 12 hours. The reaction was quenched by pouring the reaction solution into ice water, extracted and the organic phase was washed one time with 50 ml of saturated sodium bicarbonate. The organic phase was dried and then concentrated to obtain compound 120-2 (690 mg, crude product). Without further purification, the compound was directly used in the next step.

(18) ##STR00321## (2) Compound b (400 mg, 1.70 mmol), compound 120-2 (690 mg, crude product) obtained from step (1), 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 hours. After completed reaction of the starting materials according to LC-MS detection, the reaction solution was cooled to room temperature, and extracted with water (50 ml) and MTBE (50 ml). The organic phase was dried, concentrated, and separated by column chromatography to obtain compound 120 (200 mg, yield 34%), as a white solid.

(19) ##STR00322##

5. Synthesis of Compound 194

(20) Compound 4 (300 mg, 0.84 mmol), potassium carbonate (231 mg, 1.67 mmol) and acetonitrile (20 ml) were added to a 50 ml round-bottom flask, compound 194-1 (176 mg, 1.25 mmol) was added dropwise at room temperature. Heated to 85? C. and reacted for 12 hours. 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 194 (120 mg, yield 31%), as a yellow oil.

(21) ##STR00323##
Biological Activity Evaluation:

(22) The activity level standard of harmful plants destruction (i. e. growth inhibition rate) is as follows: Level 5: the growth inhibition rate is greater than 85%; Level 4: the growth inhibition rate is equal to or greater than 60% and less than 85%; Level 3: the growth inhibition rate is equal to or greater than 40% and less than 60%; Level 2: the growth inhibition rate is equal to or greater than 20% and less than 40%; Level 1: the growth inhibition rate is equal to or greater than 5% and less than 20%; Level 0: the growth inhibition rate is less than 5%;

(23) The above described growth inhibition rate is fresh weight inhibition rate.

(24) 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 after 3 weeks was listed in tables 3-4.

(25) TABLE-US-00003 TABLE 3 Activity test results of compounds (1000 g/ha ) Echinochloa Digitaria Monochoria Abutilon Galium No. crusgalli sanguinalis Vaginalis theophrasti spurium 1 5 5 5 5 5 2 5 5 5 5 5 3 5 5 5 5 5 4 5 5 5 5 5 5 5 5 5 5 5 6 5 5 5 5 5 7 5 5 5 5 5 8 5 5 5 5 5 9 5 5 5 5 5 10 5 5 5 5 5 11 5 5 5 5 5 12 5 5 5 5 5 13 5 5 5 5 5 14 5 5 5 5 5 15 5 5 5 5 5 16 5 5 5 5 5 17 5 5 5 5 5 18 5 5 5 5 5 19 5 5 5 5 5 20 5 5 5 5 5 21 5 5 5 5 5 22 5 5 5 5 5 23 5 5 5 5 5 24 5 5 5 5 5 25 5 5 5 26 5 5 5 27 5 5 5 28 5 5 5 29 5 5 5 30 5 5 5 31 5 5 5 32 5 5 5 33 5 5 5 34 5 5 5 35 5 5 5 36 5 5 5 37 5 5 5 38 5 5 5 39 5 5 5 40 5 5 5 41 5 5 5 42 5 5 5 43 5 5 5 44 5 5 5 45 5 5 5 46 5 5 5 47 5 5 5 48 5 5 5 49 5 5 5 50 5 5 5 51 5 5 5 52 5 5 5 53 5 5 5 54 5 5 5 55 5 5 5 56 5 5 5 57 5 5 5 58 5 5 5 59 5 5 5 60 5 5 5 61 5 5 5 62 5 5 5 63 5 5 5 64 5 5 5 65 5 5 5 66 5 5 5 67 5 5 5 5 5 68 5 5 5 5 5 69 5 5 5 5 5 70 5 5 5 5 5 71 5 5 5 5 5 72 5 5 5 5 5 73 5 5 5 5 5 74 5 5 5 5 5 75 5 5 5 5 5 76 5 5 5 5 5 77 5 5 5 5 5 78 5 5 5 5 5 79 5 5 5 5 5 80 5 5 5 5 5 81 5 5 5 5 5 82 5 5 5 5 5 83 5 5 5 5 5 84 5 5 5 5 5 85 5 5 5 5 5 86 5 5 5 5 5 87 5 5 5 5 5 89 5 5 5 5 5 90 5 5 5 5 5 91 5 5 5 5 5 92 5 5 5 5 5 93 5 5 5 5 5 94 5 5 5 5 5 95 5 5 5 5 5 96 5 5 5 5 5 97 5 5 5 5 5 98 5 5 5 5 5 99 5 5 5 5 5 100 5 5 5 5 5 101 5 5 5 5 5 102 5 5 5 5 5 103 5 5 5 5 5 104 5 5 5 5 5 105 5 5 5 5 5 106 5 5 5 5 5 107 5 5 5 5 5 108 5 5 5 5 5 109 5 5 5 5 5 110 5 5 5 5 5 111 5 5 5 5 5 113 5 5 5 5 5 114 5 5 5 5 5 115 5 5 5 5 5 116 5 5 5 5 5 117 5 5 5 5 5 118 5 5 5 5 5 119 5 5 5 5 5 120 5 5 5 5 5 121 5 5 5 5 5 122 5 5 5 5 5 123 5 5 5 5 5 124 5 5 5 5 5 125 5 5 5 5 5 126 5 5 5 5 5 127 5 5 5 5 5 128 5 5 5 5 5 129 5 5 5 5 5 130 5 5 5 5 5 131 5 5 5 5 5 132 5 5 5 5 5 133 5 5 5 5 5 134 5 5 5 5 5 135 5 5 5 5 5 136 5 5 5 5 5 137 5 5 5 5 5 138 5 5 5 5 5 139 5 5 5 5 5 140 5 5 5 5 5 141 5 5 5 5 5 142 5 5 5 5 5 143 5 5 5 5 5 144 5 5 5 5 5 145 5 5 5 5 5 146 5 5 5 5 5 147 5 5 5 5 5 148 5 5 5 5 5 149 5 5 5 5 5 150 5 5 5 5 5 151 5 5 5 5 5 152 5 5 5 5 5 153 5 5 5 5 5 154 5 5 5 5 5 155 5 5 5 5 5 156 5 5 5 5 5 157 5 5 5 5 5 158 5 5 5 5 5 159 5 5 5 5 5 160 5 5 5 5 5 161 5 5 5 5 5 162 5 5 5 5 5 163 5 5 5 5 5 164 5 5 5 5 5 165 5 5 5 5 5 166 5 5 5 5 5 167 5 5 5 5 5 168 5 5 5 5 5 169 5 5 5 5 5 170 5 5 5 5 5 171 5 5 5 5 5 172 5 5 5 5 5 173 5 5 5 5 5 174 5 5 5 5 5 175 5 5 5 5 5 176 5 5 5 5 5 177 5 5 5 5 5 178 5 5 5 5 5 179 5 5 5 5 5 180 5 5 5 5 5 181 5 5 5 5 5 182 5 5 5 5 5 183 5 5 5 5 5 184 5 5 5 5 5 185 5 5 5 5 5 186 5 5 5 5 5 187 5 5 5 5 5 188 5 5 5 5 5 189 5 5 5 5 5 190 5 5 5 5 5 191 5 5 5 5 5 192 5 5 5 5 5 193 5 5 5 5 5 194 5 5 5 5 5 195 5 5 5 5 5 196 5 5 5 5 5 197 5 5 5 5 5 198 5 5 5 5 5 199 5 5 5 5 5 200 5 5 5 5 5 201 5 5 5 5 5 202 5 5 5 5 5 203 5 5 5 5 5 204 5 5 5 5 5 205 5 5 5 5 5 206 5 5 5 5 5 207 5 5 5 5 5 208 5 5 5 5 5 209 5 5 5 5 5 210 5 5 5 5 5 211 5 5 5 5 5 212 5 5 5 5 5 213 5 5 5 5 5 214 5 5 5 5 5 215 5 5 5 5 5 216 5 5 5 5 5 217 5 5 5 5 5 218 5 5 5 5 5 219 5 5 5 5 5 220 5 5 5 5 5 221 5 5 5 5 5 222 5 5 5 5 5 223 5 5 5 5 5 224 5 5 5 5 5 225 5 5 5 5 5 226 5 5 5 5 5 227 5 5 5 5 5 228 5 5 5 5 5 229 5 5 5 5 5 230 5 5 5 5 5 231 5 5 5 5 5 232 5 5 5 5 5 233 5 5 5 5 5 234 5 5 5 5 5 235 5 5 5 5 5 236 5 5 5 5 5 237 5 5 5 5 5 238 5 5 5 5 5 239 5 5 5 5 5

(26) TABLE-US-00004 TABLE 4 Test results of post-emergence weeds Japonica Indica Cyperus Echinochloa No. rice rice iria crusgalli 4 0 0 5 5 7 0 0 5 5 12 0 0 5 5 20 0 0 5 5 67 0 0 5 5 75 0 0 5 5 76 0 0 5 5 85 0 0 5 5 120 0 0 5 5 128 0 0 5 5 140 0 0 5 5 185 0 0 5 5 Control compound A 3 3 5 5 (600 g/ha ) Control compound A 2 3 4 4 (300 g/ha ) Bispyribac-sodium 4 2 2 1 (100 g/ha ) Note: the application dose was active ingredient 600 g/ha, plus water 450 kg/ha. Echinochloa crusgalli and Cyperus iria were collected from Hunan province of China, and were resistant to ALS inhibitor herbicides. Control compound A:

(27) TABLE-US-00005 TABLE 5 Comparison results of post-emergence weed test Japonica Indica Cyperus Echinochloa Digitaria Leptochloa Setaria Echinochloa No. rice rice iria crusgalli sanguinalis chinensis viridis phyllopogon 238 (600 0 0 5 5 5 5 5 4 g/ha ) Control 2 2 3 3 2 2 2 2 compound B (600 g/ha ) Control compound B:

(28) The control compounds are known. Due to poor safety and low selectivity, they are hardly available for commercial application. Unexpectedly, although the structures of the present invention are similar to that of the control compounds, the safety of the present invention is greatly improved while retaining the efficacy of the control compound and they have good selectivity to key grasses, broadleaf weeds as well as sedges in rice, thus they have good commercial value, especially for control of ALS resistant weeds considering their outstanding efficacy.

(29) Experiment on Weed Effect in Pre-Emergence Stage

(30) 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 after 3 weeks. It was observed that the herbicide mostly had excellent effect at the application rate of 250 g/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.

(31) 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 spurium and Stellaria media, which were resistant to ALS inhibitors.

(32) Transplanted rice safety evaluation and weed control effect evaluation in rice field:

(33) 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.

(34) 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.

(35) 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.

(36) TABLE-US-00006 TABLE 5 Test results of activity and safety (1000 g/ha ) No. Rice Monochoria Vaginalis 4 0 5 7 0 5 12 0 5 20 0 5 67 0 5 75 0 5 76 0 5 85 0 5 120 0 5 128 0 5 140 0 5 185 0 5 Penoxsulam (50 g/ha ) 1 1 Note: The seeds of Monochoria vaginalis were collected from Heilongjing Province of China. Tests indicated that the weeds were resistant to common rate of pyrazosulfuron-ethyl and penoxsulam.

(37) 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.

(38) Broadleaf crops are very sensitive to hormonal herbicides, therefore crop injuries are more likely to occur in case of spray drifting. Tests were conducted in gentle breeze for the compounds of the present invention. The formulation of the compounds of the present invention was applied by DJI unmanned gyroplane with application height of 1 m and water volume of 20 kg/ha. The use rate was 600 g/ha. The active ingredient was dissolved by acetone and diluted to aqueous solution of Tween 80. There's a soybean field at 10 meters from the application area and the height of soybean plants were about 15 cm at the application time. The control compound C was applied in the same rate and under same conditions.

(39) TABLE-US-00007 TABLE 6 Test results of activity No. Soybean 1 0 2 0 3 0 4 0 27 0 41 0 43 0 46 0 50 0 53 0 54 0 82 0 83 0 113 0 193 0 Control compound C 3 Control compound C:

(40) It can be seen that the compounds of the present invention are not only safe for rice, but also safe for surrounding crops, and will not cause damage to sensitive broad-leaved crops due to drift problems under low wind conditions. Although the structure of the control compound is similar to the compounds of the present invention, it is not safe for rice, and at the same time, it is easy to cause phytotoxicity to the surrounding sensitive broad-leaved crops. With the large-scale promotion of unmanned aerial vehicles, there is a need for the herbicides of the present invention, which are safer to the environment.

(41) 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.