4-PYRIDINYL FORMAMIDE COMPOUND OR DERIVATIVE THEREOF, PREPARATION METHOD THEREFOR, HERBICIDAL COMPOSITION AND USE THEREOF

Abstract

The invention belongs to the technical field of pesticides, and specifically relates to a 4-pyridinyl formamide compound or a derivative thereof, a preparation method therefor, a herbicidal composition and the use thereof. The 4-pyridinyl formamide compound is as represented by formula (I), wherein, X and Y each independently represent nitro, halogen, cyano, formyl, thiocyano, mercapto, etc.; and M represents an unsubstituted or substituted structure (II). The compound, and the derivative and the composition thereof have excellent herbicidal activity and a higher crop safety, and establish good selectivity, especially for key crops such as wheat and rice.

Description

TECHNICAL FIELD

The invention belongs to the technical field of pesticides, and specifically relates to a 4-pyridinyl formamide compound or derivative thereof, preparation method therefor, herbicidal composition and use thereof.

TECHNICAL BACKGROUND

Weed control is one of the most important links in the course of achieving high-efficiency agriculture. Various herbicides are available in the market, for example, WO2013087577A1 etc. disclose certain arylformamide compounds and their use as herbicides. However, due to the continuous expansion of the market, the resistance of weeds, the service life of chemicals and the economical efficiency of chemicals, as well as the increasing emphasis on the environment, especially the resistance of the mainstream ALS inhibitor and ACCe inhibitor herbicides is becoming more and more serious. In rice fields and wheat fields, more and more efficient, selective herbicides that can solve resistance are needed. This requires scientists to continuously research and develop new high-efficiency, safe, economic herbicides with different action modes.

Invention Contents

The present invention provides a 4-pyridinyl formamide compound or derivative thereof, preparation method therefor, herbicidal composition and use thereof. The compound has excellent herbicidal activity and a higher crop safety, and establishes good selectivity, especially for key crops such as wheat and rice.

The technical solution adopted by the invention is as follows:

A 4-pyridinyl formamide compound or derivative thereof, as shown in Formula I:

Wherein, X, and Y each independently represent nitro, halogen, cyano, formyl, thiocyano, mercapto; alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, or cycloalkenylalkyl, which is with or without halogen; OR¹, COR¹, COOR¹, OCOR¹, OCOOR¹, NR³SO₂R², OSO₂R², S(O)_mR², NR³COR¹, NR³COOR¹, C(O)NR³OR¹, SO₂OR¹, C(O)NR⁴R⁵, NR³C(O)NR⁴R⁵, OC(O)NR⁴R⁵, SO₂NR⁴R⁵, C(S)R¹, C(S)OR¹, C(S)SR², C(O)SR², SC(O)R¹, SC(S)R¹, OC(S)R¹, -alkyl-C(S)R¹, -alkyl-C(S)OR¹, -alkyl-C(O)SR¹, -alkyl-C(S)SR¹, -alkyl-SC(O)R¹, -alkyl-OC(S)R¹, -alkyl-SC(S)R¹, —O-alkyl-NR⁴R⁵, —S-alkyl-NR⁴R⁵, -alkyl-O-alkyl-NR⁴R⁵, -alkyl-S-alkyl-NR⁴R⁵, -alkyl-(C═S)_n—NR⁴R⁵, —NH-alkyl-NR⁴R⁵, -alkyl-OR¹, -alkyl-COR¹, -alkyl-CO₂R¹, -alkyl-OCOR¹, -alkyl-NR³COR¹, -alkyl-SO₂OR¹, -alkyl-NR³SO₂R², -alkyl-OSO₂R², -alkyl-S(O)_mR², -alkyl-CONR⁴R⁵, -alkyl-SO₂NR⁴R⁵, NR⁴R⁵,

P(O)(OR⁶)₂, CH₂P(O)(OR⁶)₂, SO₂NR⁴R⁵-alkyl-S(O)_mR², -alkyl-CN, -alkylaryl, -alkylheteroaryl, -alkylheterocyclyl, aryl, heteroaryl, or heterocyclyl;

R¹, R³, R⁴, and R⁵ each independently represent hydrogen, aryl, arylalkyl, heteroaryl, heteroarylalkyl, alkyl, halogenated alkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkyl, halogenated cycloalkyl, alkoxyalkyl, or cycloalkylalkyl, wherein the last 10 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR⁷, S(O)_mR⁹, NR⁷R⁸, NR⁸OR⁷, COR⁷, OCOR⁷, SCOR⁷, NR⁸COR⁷, CO₂R⁷, COSR⁷, CONR⁷R⁸, and alkoxyalkoxycarbonyl;

R² represents aryl, arylalkyl, heteroaryl, heteroarylalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl, wherein the last 5 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR⁷, S(O)_mR⁹, NR⁷R⁸, NR⁸OR⁷, COR⁷, OCOR⁷, SCOR⁷, NR⁸COR⁷, CO₂R⁷, COSR⁷, CONR⁷R⁸, and alkoxyalkoxycarbonyl;

R⁶ represents methyl, or ethyl;

R⁷, and R⁸ each independently represent hydrogen, alkyl, alkenyl, or alkynyl;

R⁹ represents alkyl, alkenyl, or alkynyl;

M represents

which is unsubstituted or substituted;

R₁₁ represents hydrogen, halogen, cyano, nitro, alkyl which is unsubstituted or substituted with a substituent selected from R₁₃, cycloalkyl which is unsubstituted or substituted with a substituent selected from R₁₄, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkenyl, NH₂, aminoacyl, carboxyl, alkoxyalkoxycarbonyl, OR₁₅, -alkyl-OR₁₅, C(O)R₁₆, -alkyl-C(O)R₁₆, C(O)OR₁₆, -alkyl-C(O)OR₁₆, S(O)_mR₁₆, -alkyl-S(O)_mR₁₆, —N(R₁₆)₂, —NHR₁₆, —C(O)NHR₁₆, —C(O)N(R₁₆)₂, —NHC(O)Rn, heterocyclyl, heterocyclylalkyl, heterocyclyloxy, heterocyclylcarbonyl, aryl, arylalkyl, aryloxy, arylcarbonyl, heteroaryl, heteroarylalkyl, heteroaryloxy, or heteroarylcarbonyl;

R₁₂ represents hydrogen, alkyl which is unsubstituted or substituted with a substituent selected from R₁₈, cycloalkyl, halogenated cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkenyl, alkoxyalkyl, alkylthioalkyl, alkoxycarbonylalkyl, aryl, or arylalkyl;

when M is

—(CH₂)₄— or —CH═CH—CH═CH— formed by R₁₁ and R₁₂, the nitrogen atom bound to R₁₂ and the carbon atom bound to R₁₁ together form a 6-membered ring;

R₁₅ represents alkyl which is unsubstituted or substituted with a substituent selected from R₂₁, cycloalkyl, halogenated cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkenyl, or phenyl;

R₁₆ represents alkyl, halogenated alkyl, cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, or cycloalkenyl;

R₂₁ represents halogen, cyano, cycloalkyl, hydroxy, mercapto, alkoxy, C(O)R₂₂, carboxyl, alkoxycarbonyl, alkoxyalkoxycarbonyl, —S(O)_m-alkyl, heteroaryl, heterocyclyl, or phenyl which is unsubstituted or substituted with one or more groups selected from R₂₃;

R₁₇, and R₂₂ each independently represent hydrogen, alkyl, or N(R₂₄)R₂₅;

R₂₃ represents halogen, cyano, nitro, alkyl, alkyl which is unsubstituted or substituted with a substituent selected from R₃₁, cycloalkyl, halogenated cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkenyl, alkylcarbonyl, cycloalkylcarbonyl, halogenated alkylcarbonyl, halogenated cycloalkylcarbonyl, alkoxycarbonyl, halogenated alkoxycarbonyl, alkylaminocarbonyl, halogenated alkylaminocarbonyl, bis(alkyl)aminocarbonyl, OR₃₂, S(O)_mR₃₃, alkylaminosulfonyl, bis(alkyl)aminosulfonyl, NH₂, alkylamino, bis(alkyl)amino, aryl, heteroaryl, or heterocyclyl;

R₂₄, and R₂₅ each independently represent hydrogen, alkyl, or phenyl; or,

alkylidene chain formed by R₂₄ and R₂₅, and the nitrogen atom(s) bound to R₂₄ and R₂₅ together form a 3-7-membered ring, said alkylidene chain optionally contains one O, S, S(O), S(O)₂, NH, or N-alkyl and optionally substituted by oxo or thio group;

R₁₃. R₁₄, R₁₈, and R₃₁ each independently represent halogen, cyano, nitro, carboxyl, alkoxycarbonyl, alkoxyalkoxycarbonyl, S(O)_mR₄₁, OR₄₂, aryl, heteroaryl, or heterocyclyl;

R₃₂ represents hydrogen, alkyl, halogenated alkyl, cycloalkyl, halogenated cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, or cycloalkenyl;

R₃₃ represents alkyl, halogenated alkyl, cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, or cycloalkenyl;

R₄₁, and R₄₂ each independently represent hydrogen, alkyl, halogenated alkyl, cycloalkyl, halogenated cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkenyl, or phenyl;

r represents 1 or 2;

m represents 0, 1 or 2;

n represents 0, or 1;

s represents 0, 1, 2 or 3.

Preferably, X, and Y each independently represent nitro, halogen, cyano, formyl, thiocyano, mercapto; C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkyl-C1-C6 alkyl, or C3-C8 cycloalkenyl-C1-C6 alkyl, which is with or without halogen; OR¹, COR¹, COOR¹, OCOR¹, OCOOR¹, NR³SO₂R², OSO₂R², S(O)_mR², NR³COR¹, NR³COOR¹, C(O)NR³OR¹, SO₂OR¹, C(O)NR⁴R⁵, NR³C(O)NR⁴R⁵, OC(O)NR⁴R⁵, SO₂NR⁴R⁵, C(S)R¹, C(S)OR¹, C(S)SR², C(O)SR², SC(O)R₂, SC(S)R¹, OC(S)R₁, —(C1-C6)alkyl-C(S)R¹, —(C1-C6)alkyl-C(S)OR¹, —(C1-C6)alkyl-C(O)SR¹, —(C1-C6)alkyl-C(S)SR¹, —(C1-C6)alkyl-SC(O)R¹, —(C1-C6)alkyl-OC(S)R¹, —(C1-C6)alkyl-SC(S)R¹, —O—(C1-C6)alkyl-NR⁴R⁵, —S—(C1-C6)alkyl-NR⁴R⁵, —(C1-C6)alkyl-O—(C1-C6)alkyl-NR⁴R⁵,—(C1-C6)alkyl-S—(C1-C6)alkyl-NR⁴R⁵, —(C1-C6)alkyl-(C═S)_n—NR⁴R⁵, —NH—(C1-C6)alkyl-NR⁴R⁵, —(C1-C6)alkyl-OR¹, —(C1-C6)alkyl-COR¹, —(C1-C6)alkyl-CO₂R¹, —(C1-C6)alkyl-OCOR¹, —(C1-C6)alkyl-NR³COR¹, —(C1-C6)alkyl-SO₂OR¹, —(C1-C6)alkyl-NR³SO₂R², —(C1-C6)alkyl-OSO₂R², -alkyl-S(O)_mR², —(C1-C6)alkyl-CONR⁴R⁵, —(C1-C6)alkyl-SO₂NR⁴R⁵,NR⁴R⁵,

P(O)(OR⁶)₂, CH₂P(O)(OR⁶)₂, SO₂NR⁴R⁵—(C1-C6)alkyl-S(O)_mR², —(C1-C6)alkyl-CN, —(C1-C6)alkylaryl, —(C1-C6)alkylheteroaryl, —(C1-C6)alkylheterocyclyl, aryl, heteroaryl, or heterocyclyl;

R¹, R³, R⁴, and R⁵ each independently represent hydrogen, aryl, aryl-C1-C6 alkyl, heteroaryl, heteroaryl-C1-C6 alkyl, C1-C8 alkyl, halogenated C1-C8 alkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C1-C8 alkoxy-C1-C6 alkyl, or C3-C8 cycloalkyl-C1-C6 alkyl, wherein the last 10 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR⁷, S(O)_mR⁹, NR⁷R⁸, NR⁸OR⁷, COR⁷, OCOR⁷, SCOR⁷, NR⁸COR⁷, CO₂R⁷, COSR⁷, CONR⁷R⁸, and C1-C8 alkoxy-C1-C6 alkoxycarbonyl;

R² represents aryl, aryl-C1-C6 alkyl, heteroaryl, heteroaryl-C1-C6 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, or C3-C8 cycloalkyl-C1-C6 alkyl, wherein the last 5 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR⁷, S(O)_mR⁹, NR⁷R⁸, NR⁸OR⁷, COR⁷, OCOR⁷, SCOR⁷, NR⁸COR⁷, CO₂R⁷, COSR⁷, CONR⁷R⁸, and C1-C8 alkoxy-C1-C6 alkoxycarbonyl;

R⁶ represents methyl, or ethyl;

R⁷, and R⁸ each independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl;

R⁹ represents C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl;

M represents

which is unsubstituted or substituted;

R₁₁ represents hydrogen, halogen, cyano, nitro, C1-C8 alkyl which is unsubstituted or substituted with a substituent selected from R₁₃, C3-C8 cycloalkyl which is unsubstituted or substituted with a substituent selected from R₁₄, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, NH₂, aminoacyl, carboxyl, C1-C8 alkoxy-C1-C6 alkoxycarbonyl, OR₁₅, —(C1-C6)alkyl-OR₁₅, C(O)R₁₆, —(C1-C6)alkyl-C(O)R₁₆, C(O)OR₁₆, —(C1-C6)alkyl-C(O)OR₁₆, S(O)_mR₁₆, —(C1-C6)alkyl-S(O)_mR₁₆, —N(R₁₆)₂, —NHR₁₆, —C(O)NHR₁₆, —C(O)N(R₁₆)₂, —NHC(O)Rn, heterocyclyl, heterocyclyl-C1-C6 alkyl, heterocyclyloxy, heterocyclylcarbonyl, aryl, aryl-C1-C6 alkyl, aryloxy, arylcarbonyl, heteroaryl, heteroaryl-C1-C6 alkyl, heteroaryloxy, or heteroarylcarbonyl;

R₁₂ represents hydrogen, C1-C8 alkyl which is unsubstituted or substituted with a substituent selected from R₁₈, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, C1-C8 alkoxy-C1-C6 alkyl, C1-C8 alkylthio-C1-C6 alkyl, C1-C8 alkoxycarbonyl-C1-C6 alkyl, aryl, or aryl-C1-C6 alkyl;

when M is

—(CH₂)₄— or —CH═CH—CH═CH— formed by R₁₁ and R₁₂, the nitrogen atom bound to R₁₂ and the carbon atom bound to R₁₁ together form a 6-membered ring;

R₁₅ represents C1-C8 alkyl which is unsubstituted or substituted with a substituent selected from R₂₁, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, or phenyl;

R₁₆ represents C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, or C3-C8 cycloalkenyl;

R₂₁ represents halogen, cyano, C3-C8 cycloalkyl, hydroxy, mercapto, C1-C8 alkoxy, C(O)R₂₂, carboxyl, C1-C8 alkoxy carbonyl, C1-C8 alkoxy-C1-C6 alkoxy carbonyl, —S(O)_m—(C1-C8)alkyl, heteroaryl, heterocyclyl, or phenyl which is unsubstituted or substituted with one or more groups selected from R₂₃;

R₁₇, and R₂₂ each independently represent hydrogen, C1-C8 alkyl, or N(R₂₄)R₂₅;

R₂₃ represents halogen, cyano, nitro, C1-C8 alkyl, C1-C8 alkyl which is unsubstituted or substituted with a substituent selected from R₃₁, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, C1-C8 alkylcarbonyl, C3-C8 cycloalkylcarbonyl, halogenated C1-C8 alkylcarbonyl, halogenated C3-C8 cycloalkylcarbonyl, C1-C8 alkoxy carbonyl, halogenated C1-C8 alkoxy carbonyl, C1-C8 alkylaminocarbonyl, halogenated C1-C8 alkylaminocarbonyl, bis(C1-C8 alkyl)aminocarbonyl, OR₃₂, S(O)_mR₃₃, C1-C8 alkylaminosulfonyl, bis(C1-C8 alkyl)aminosulfonyl, NH₂, C1-C8 alkylamino, bis(C1-C8 alkyl)amino, aryl, heteroaryl, or heterocyclyl;

R₂₄, and R₂₅ each independently represent hydrogen, C1-C8 alkyl, or phenyl; or,

C2-C8 alkylidene chain formed by R₂₄ and R₂₅, and the nitrogen atom(s) bound to R₂₄ and R₂₅ together form a 3-7-membered ring, said C2-C8 alkylidene chain optionally contains one O, S, S(O), S(O)₂, NH, or N-alkyl and optionally substituted by oxo or thio group;

R₁₃, R₁₄, R₁₈, and R₃₁ each independently represent halogen, cyano, nitro, carboxyl, C1-C8 alkoxycarbonyl, C1-C8 alkoxy-C1-C8 alkoxy carbonyl, S(O)_mR₄₁, OR₄₂, aryl, heteroaryl, or heterocyclyl;

R₃₂ represents hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, or C3-C8 cycloalkenyl;

R₃₃ represents C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, or C3-C8 cycloalkenyl;

R₄₁, and R₄₂ each independently represent hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, or phenyl;

r represents 1, or 2;

m represents 0, 1, or 2;

n represents 0, or 1;

s represents 0, 1, 2, or 3.

More preferably, X represents nitro, halogen, cyano, formyl, thiocyano, mercapto; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkyl-C1-C3 alkyl, or C3-C6 cycloalkenyl-C1-C3 alkyl, which is with or without halogen; OR¹, COR¹, COOR¹, OCOR¹, OCOOR¹, NR³SO₂R², OSO₂R², S(O)_mR², NR³COR¹, NR³COOR¹, C(O)NR³OR¹, SO₂OR¹, C(O)NR⁴R⁵, NR³C(O)NR⁴R⁵, OC(O)NR⁴R⁵, SO₂NR⁴R⁵, C(S)R¹, C(S)OR¹, C(S)SR², C(O)SR², SC(O)R¹, SC(S)R¹, OC(S)R¹, —(C1-C3)alkyl-C(S)R¹, —(C1-C3)alkyl-C(S)OR¹, —(C1-C3)alkyl-C(O)SR¹, —(C1-C3)alkyl-C(S)SR¹, —(C1-C3)alkyl-SC(O)R¹, —(C1-C3)alkyl-OC(S)R¹, —(C1-C3)alkyl-SC(S)R¹, —O—(C1-C3)alkyl-NR⁴R⁵, —S—(C1-C3)alkyl-NR⁴R⁵, —(C1-C3)alkyl-O—(C1-C3)alkyl-NR⁴R⁵, —(C1-C3)alkyl-S—(C1-C3)alkyl-NR⁴R⁵, —(C1-C3)alkyl-(C═S)_n—NR⁴R⁵, —NH—(C1-C3)alkyl-NR⁴R⁵, —(C1-C3)alkyl-OR¹, —(C1-C3)alkyl-COR¹, —(C1-C3)alkyl-CO₂R¹, —(C1-C3)alkyl-OCOR¹, —(C1-C3)alkyl-NR³COR¹, —(C1-C3)alkyl-SO₂OR¹, —(C1-C3)alkyl-NR³SO₂R², —(C1-C3)alkyl-OSO₂R², -alkyl-S(O)_mR², —(C1-C3)alkyl-CONR⁴R⁵, —(C1-C3)alkyl-SO₂NR⁴R⁵,NR⁴R⁵,

P(O)(OR⁶)₂, CH₂P(O)(OR⁶)₂, SO₂NR⁴R⁵—(C1-C3)alkyl-S(O)_mR², —(C1-C3)alkyl-CN, —(C1-C3)alkylaryl, —(C1-C3)alkylheteroaryl, —(C1-C3)alkylheterocyclyl, aryl, heteroaryl, or heterocyclyl;

Y represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkenyl, which is with or without halogen; OR¹, S(O)_mR², NR⁴R⁵, heterocyclyl, aryl, or heteroaryl;

R¹, R³, R⁴, and R⁵ each independently represent hydrogen, aryl, aryl-C1-C3 alkyl, heteroaryl, heteroaryl-C1-C3 alkyl, C1-C6 alkyl, halogenated C1-C6 alkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C1-C6 alkoxy-C1-C3 alkyl, or C3-C6 cycloalkyl-C1-C3 alkyl, wherein the last 10 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR⁷, S(O)_mR⁹, NR⁷R⁸, NR⁸OR⁷, COR⁷, OCOR⁷, SCOR⁷, NR⁸COR⁷, CO₂R⁷, COSR⁷, CONR⁷R⁸, and C1-C6 alkoxy-C1-C3 alkoxycarbonyl;

R² represents aryl, aryl-C1-C3 alkyl, heteroaryl, heteroaryl-C1-C3 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkyl-C1-C3 alkyl, wherein the last 5 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR⁷, S(O)_mR⁹, NR⁷R⁸, NR⁸OR⁷, COR⁷, OCOR⁷, SCOR⁷, NR⁸COR⁷, CO₂R⁷, COSR⁷, CONR⁷R⁸, and C1-C6 alkoxy-C1-C3 alkoxycarbonyl;

R⁶ represents methyl, or ethyl;

R⁷, and R⁸ each independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl,

R⁹ represents C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl;

M represents

which is unsubstituted or substituted;

R₁₁ represents hydrogen, halogen, cyano, nitro, C1-C6 alkyl which is unsubstituted or substituted with a substituent selected from R₁₃, C3-C6 cycloalkyl which is unsubstituted or substituted with a substituent selected from R₁₄, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkenyl, NH₂, aminoacyl, carboxyl, C1-C6 alkoxy-C1-C3 alkoxy carbonyl, OR₁₅, —(C1-C3)alkyl-OR₁₅, C(O)R₁₆, —(C1-C3)alkyl-C(O)R₁₆, C(O)OR₁₆, —(C1-C3)alkyl-C(O)OR₁₆, S(O)_mR₁₆, —(C1-C3)alkyl-S(O)_mR₁₆, —N(R₁₆)₂, —NHR₁₆, —C(O)NHR₁₆, —C(O)N(R₁₆)₂, —NHC(O)Rn, heterocyclyl, heterocyclyl-C1-C3 alkyl, heterocyclyloxy, heterocyclylcarbonyl, aryl, aryl-C1-C3 alkyl, aryloxy, arylcarbonyl, heteroaryl, heteroaryl-C1-C3 alkyl, heteroaryloxy, or heteroarylcarbonyl;

R₁₂ represents hydrogen, C1-C6 alkyl which is unsubstituted or substituted with a substituent selected from R₁₈, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkenyl, C1-C6 alkoxy-C1-C3 alkyl, C1-C6 alkylthio-C1-C3 alkyl, C1-C6 alkoxycarbonyl-C1-C3 alkyl, aryl, or aryl-C1-C3 alkyl;

when M is

—(CH₂)₄— or —CH═CH—CH═CH— formed by R₁₁ and R₁₂, the nitrogen atom bound to R₁₂ and the carbon atom bound to Rn together form a 6-membered ring;

R₁₅ represents C1-C6 alkyl which is unsubstituted or substituted with a substituent selected from R₂₁, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkenyl, or phenyl;

R₁₆ represents C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, or C3-C6 cycloalkenyl;

R₂₁ represents halogen, cyano, C3-C6 cycloalkyl, hydroxy, mercapto, C1-C6 alkoxy, C(O)R₂₂, carboxyl, C1-C6 alkoxy carbonyl, C1-C6 alkoxy-C1-C3 alkoxy carbonyl, —S(O)_m—(C1-C6)alkyl, heteroaryl, heterocyclyl, or phenyl which is unsubstituted or substituted with 1˜3 groups selected from R₂₃;

R₁₇, and R₂₂ each independently represent hydrogen, C1-C6 alkyl, or N(R₂₄)R₂₅;

R₂₃ represents halogen, cyano, nitro, C1-C6 alkyl, C1-C6 alkyl which is unsubstituted or substituted with a substituent selected from R₃₁, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkenyl, C1-C6 alkylcarbonyl, C3-C6 cycloalkylcarbonyl, halogenated C1-C6 alkylcarbonyl, halogenated C3-C6 cycloalkylcarbonyl, C1-C6 alkoxycarbonyl, halogenated C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, halogenated C1-C6 alkylaminocarbonyl, bis(C1-C6 alkyl)aminocarbonyl, OR₃₂, S(O)_mR₃₃, C1-C6 alkylaminosulfonyl, bis(C1-C6 alkyl)aminosulfonyl, NH₂, C1-C6 alkylamino, bis(C1-C6 alkyl)amino, aryl, heteroaryl, or heterocyclyl;

R₂₄, and R₂₅ each independently represent hydrogen, C1-C6 alkyl, or phenyl; or,

C2-C6 alkylidene chain formed by R₂₄ and R₂₅, and the nitrogen atom(s) bound to R₂₄ and R₂₅ together form a 3-7-membered ring, said C2-C6 alkylidene chain optionally contains one O, S, S(O), S(O)₂, NH, or N-alkyl and optionally substituted by oxo or thio group;

R₁₃, R₁₄, R₁₈, and R₃₁ each independently represent halogen, cyano, nitro, carboxyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxy-C1-C6 alkoxy carbonyl, S(O)_mR₄₁, OR₄₂, aryl, heteroaryl, or heterocyclyl;

R₃₂ represents hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, or C3-C6 cycloalkenyl;

R₃₃ represents C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, or C3-C6 cycloalkenyl;

R₄₁, and R₄₂ each independently represent hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkenyl, or phenyl;

r represents 1, or 2;

m represents 0, 1, or 2;

n represents 0, or 1;

s represents 0, 1, 2, or 3.

Further preferably, X represents halogen, nitro, cyano, OR¹, S(O)_mR², NR COR¹. NR⁴R⁵,

C1-C6 alkoxy-C1-C3 alkyl; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C6 cycloalkyl, which is with or without halogen;

or phenyl which is unsubstituted or substituted with 1, 2, or 3 groups selected from halogen, and C1-C6 alkoxy;

Y represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkenyl, which is with or without halogen; OR¹, S(O)_mR², NR⁴R⁵, heterocyclyl, aryl, or heteroaryl;

R¹, R³, R⁴, and R⁵ each independently represent hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, phenyl; or benzyl which is unsubstituted or substituted with 1, 2, or 3 groups selected from halogen, and C1-C6 alkoxy;

R² represents C1-C6 alkyl, or halogenated C1-C6 alkyl;

M represents

which is unsubstituted or substituted;

R₁₁ represents hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, halogen, C1-C6 alkylamino, bis(C1-C6 alkyl)amino, cyano, nitro, C1-C6 alkylcarbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkoxycarbonyl-C1-C3 alkyl, aminocarbonyl, C1-C6 alkylcarbonylamino, C1-C6 alkoxy-C1-C3 alkyl, C1-C6 alkylthio-C1-C3 alkyl, C1-C6 alkylsulfinyl-C1-C3 alkyl, C1-C6 alkylsulfonyl-C1-C3 alkyl; or benzyl, phenoxy, benzoyl, pyridyl,

which is unsubstituted or substituted with 1, 2, or 3 groups selected from halogen, and C1-C6 alkoxy;

R₁₂ represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C1-C6 alkoxy-C1-C3 alkyl, C1-C6 alkylthio-C1-C3 alkyl, C1-C6 alkoxycarbonyl-C1-C3 alkyl; or phenyl, or benzyl which is unsubstituted or substituted with at least one group selected from halogen, and halogenated C1-C6 alkyl;

r represents 1, or 2;

m represents 0, 1, or 2;

wherein, the “heterocyclyl” is

the “aryl” is phenyl, naphthyl, or

which is unsubstituted or substituted; the “heteroaryl” is

which is unsubstituted or substituted; the aforementioned “substituted” respectively refers to being substituted by 1˜3 groups selected from: halogen, nitro, cyano, thiocyano, cyano C1-C3 alkyl, hydroxy, hydroxy C1-C3 alkyl, mercapto, carboxyl, formyl,

phenyl, phenyl substituted by C1-C6 alkyl, phenoxy, benzyloxy; amino, aminoalkyl, or aminocarbonyl group which is unsubstituted or substituted by one or two groups selected from C1-C6 alkyl, COR″, and COOR″; and C1-C6 alkyl, C2-C6 alkenyl, C3-C6 cycloalkyl, C1-C6 alkoxy-C1-C3 alkyl, C1-C6 alkylthio-C1-C3 alkyl, C1-C6 alkylcarbonylthio, C3-C6 cycloalkyl substituted with C1-C6 alkyl, OR″, SR″, SOR″, COR″, COOR″, or SO₂R″, which is with or without halogen; or, two adjacent substitutable positions of the above-mentioned “heterocyclyl”, “aryl”, “heteroaryl” groups are linked with —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O—, or —CH═CH—CH═CH— group to form a ring, wherein the —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O—, or —CH═CH—CH═CH— group, which is with or without halogen;

R′ each independently represents hydrogen, C1-C6 alkyl, C1-C6 alkylcarbonyl, halogenated C1-C6 alkyl,

C1-C6 alkoxycarbonyl, C1-C6 alkoxy-C1-C3 alkyl, or benzyl;

R″ each independently represents C1-C6 alkyl, or C2-C6 alkenyl.

Further preferably, X represents chlorine, fluorine, bromine, methyl, ethyl, isopropyl, vinyl, allyl, ethynyl, cyclopropyl, trifluoromethyl,

hydroxy, methoxy, ethyloxy, methylthio, ethylthio,

nitro, cyano, methylsulfinyl, ethylsulfinyl, methylsulfonyl, amino, monomethylamino, dimethylamino, acetamido,

phenyl, phenoxy, or 4-fluorophenyl;

Y represents methyl, ethyl, vinyl, methoxy,

phenoxy, benzyloxy, methylthio, propylthio, tert-butylthio, benzylthio, 4-methoxybenzylthiol, propylsulfinyl, amino, monomethylamino, dimethylamino, anilino, p-methoxybenzylamino, tert-butyl, cyclopropyl, cyclohexyl,

heterocyclyl, aryl, or heteroaryl;

M represents

which is unsubstituted or substituted;

R₁₁ each independently represents hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, monochloromethyl, trifluoromethyl, methoxy, isopropyloxy, methylthio, fluorine, chlorine, bromine, iodine, dimethylamino, ethylamino, cyano, nitro, acetyl, methoxycarbonyl; phenyl which is unsubstituted or substituted by 1, 2, or 3 groups selected from chlorine, and methoxy; pyridyl,

R₁₂ each independently represents hydrogen, methyl, ethyl, n-propyl, isopropyl, allyl,

or phenyl, or benzyl which is unsubstituted or substituted by 1,2, or 3 groups selected from chlorine, and trifluoromethyl;

r represents 1, or 2:

wherein, the “heterocyclyl” is

the “aryl” is phenyl, naphthyl, or

which is unsubstituted or substituted; the “heteroaryl” is

which is unsubstituted or substituted; the aforementioned “substituted” refers to being substituted by 1, 2, or 3 groups selected from: methyl, ethyl, isopropyl, n-butyl, tert-butyl, n-pentyl, vinyl, cyclopropyl,

fluorine, chlorine, bromine, iodine, monobromomethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propoxy, butoxy, trifluoromethoxy, hydroxyl, hydroxymethyl, amino, cyano, cyanomethyl, thiocyano, mercapto, nitro, carboxy, formyl, acetyl, methoxycarbonyl, tert-butyloxycarbonyl, methylthio, isopropylthio, methylsulfinyl, methylsulfonyl,

dimethylamino, aminocarbonyl, dimethylaminocarbonyl, acetylamino,

phenyl, 4-ethylphenyl, phenoxy, and benzyloxy; or, two adjacent substitutable positions of the above-mentioned “aryl”, “heteroaryl” groups are linked with —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O—, or —CH═CH—CH═CH— group to form a ring, wherein the —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O—, or —CH═CH—CH═CH— group is with or without halogen;

R′ each independently represents hydrogen, methyl, ethyl, n-propyl, isopropyl, difluoromethyl, 3,3,3-trifluoroethyl, benzyl,

It should be particularly pointed out that when X is fluorine, Y is not amino, monomethylamino, monoethylamino and monopropylamino; when M is

X and Y are not methyl at the same time.

The structural formula of the derivative is

wherein Q represents hydrogen. -alkyl-Q₁, OQ₂, SQ₂, COQ₂, COOQ₂, CON(Q₃)₂, N(Q₃)₂, NQ₄COOQ₂, NQ₄CON(Q₃)₂; alkyl, alkenyl, alkynyl, or cycloalkyl, which is with or without halogen; or arylalkyl, or heteroarylalkyl, which is unsubstituted or substituted;

Q₁ each independently represents alkenyl, alkynyl, or cycloalkyl, which is with or without halogen; CN, OQ₁₁, OCOQ₁₁, COOQ₁₁, COQ₁₁, —O—(C═O)—O-Q₁₁, OSO₂Q₁₂, SO₂OQ₁₁, —S(O)_pQ₁₂, N(Q₁₃)₂, CON(Q₁₃)₂, SO₂N(Q₁₃)₂, NQ₁₄COQ₁₁, NQ₁₄SO₂Q₁₂, or —O—(C═O)—N(Q₁₃)₂;

Q₂, and Q₁₁ each independently represent hydrogen; alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, or alkoxyalkyl, which is with or without halogen; or heterocyclyl, heterocyclylalkyl, heterocyclyloxyalkyl, aryl, arylalkyl, aryloxyalkyl, heteroaryl, heteroarylalkyl, or heteroaryloxyalkyl, which is unsubstituted or substituted;

Q₁₂ each independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, or alkoxyalkyl, which is with or without halogen; or heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl, which is unsubstituted or substituted;

Q₃, Q₄, Q₁₃, and Q₁₄ each independently represent hydrogen, nitro, alkoxyaminocarbonyl, trialkylsilyl, dialkylphosphonyl, N(Q₂₁)₂, CON(Q₂₁)₂, OQ₂₁, COQ₂₁, CO₂Q₂₁, COSQ₂₁, OCOQ₂₁, S(O)_pQ₂₂, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, cycloalkenyl, halocycloalkyl, alkoxyalkyl, cycloalkylalkyl, aryl, arylalkyl, aryloxy, aryloxyalkyl, arylalkyloxy, arylcarbonyl, arylsulfonyl, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroaryloxyalkyl, heteroarylalkyloxy, heteroarylcarbonyl, heteroarylsulfonyl, heterocyclyl, heterocyclylalkyl, heterocyclyloxy, heterocyclooxyalkyl, heterocyclylalkyloxy, heterocyclylcarbonyl, heterocyclylsulfonyl, aryl-NQ₂₁-alkyl, heteroaryl-NQ₂₁-alkyl, or heterocyclyl-NQ₂₁-alkyl, wherein the last 35 groups as mentioned each are independently substituted by 0, 1, 2, or 3 groups selected from the group consisting of cyano, halogen, nitro, cyanothio, OQ₂₁, S(O)_pQ₂₂, N(Q₂₁)₂, NQ₂₁OQ₂₁, COQ₂₁, OCOQ₂₁, SCOQ₂₂, NQ₂₁COQ₂₁, NQ₂₁SO₂Q₂₂, CO₂Q₂₁, COSQ₂₁, CON(Q₂₁)₂, and alkoxyalkoxy carbonyl;

Q₂₁ each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl;

Q₂₂ each independently represents alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl;

p each independently represents 0, 1, or 2.

Preferably, Q represents hydrogen, —(C1-C6)alkyl-Q₁, OQ₂, SQ₂, COQ₂, COOQ₂, CON(Q₃)₂, N(Q₃)₂, NQ₄COOQ₂, NQ₄CON(Q₃)₂; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C6 cycloalkyl, which is with or without halogen; or aryl-C1-C6 alkyl, or heteroaryl-C1-C6 alkyl, which is unsubstituted or substituted;

Q₁ each independently represents C2-C6 alkenyl, C2-C6 alkynyl, or C3-C6 cycloalkyl, which is with or without halogen; CN, OQ₁₁, OCOQ₁₁, COOQ₁₁, COQ₁₁, —O—(C═O)—O-Q₁₁, OSO₂Q₁₂, SC₂OQ₁₁, —S(O)_pQ₁₂, N(Q₁₃)₂, CON(Q₁₃)₂, SO₂N(Q₁₃)₂, NQ₁₄COQ₁₁, NQ₁₄SO₂Q₁₂, or —O—(C═O)—N(Q₁₃)₂;

Q₂, and Q₁₁ each independently represent hydrogen; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkenyl, or C1-C6 alkoxy-C1-C6 alkyl, which is with or without halogen; or heterocyclyl, heterocyclyl-C1-C6 alkyl, heterocyclyloxy-C1-C6 alkyl, aryl, aryl-C1-C6 alkyl, aryloxy-C1-C6 alkyl, heteroaryl, heteroaryl-C1-C6 alkyl, or heteroaryloxy-C1-C6 alkyl, which is unsubstituted or substituted;

Q₁₂ each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkenyl, or C1-C6 alkoxy-C1-C6 alkyl, which is with or without halogen; or heterocyclyl, heterocyclyl-C1-C6 alkyl, aryl, aryl-C1-C6 alkyl, heteroaryl, or heteroaryl-C1-C6 alkyl, which is unsubstituted or substituted;

Q₃, Q₄, Q₁₃, and Q₁₄ each independently represent hydrogen, nitro, C1-C6 alkoxyaminocarbonyl, tri-C1-C6 alkylsilyl, di-C1-C6 dialkylphosphonyl, N(Q₂₁)₂, CON(Q₂₁)₂, OQ₂₁, COQ₂₁, CO₂Q₂₁, COSQ₂₁, OCOQ₂₁, S(O)_pQ₂₂, C1-C6 alkyl, halo-C1-C6 alkyl, C2-C6 alkenyl, halo-C2-C6 alkenyl, C2-C6 alkynyl, halo-C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, halo-C3-C6 cycloalkyl, C1-C6 alkoxy-C1-C6 alkyl, C3-C6 cycloalkyl-C1-C6 alkyl, aryl, aryl-C1-C6 alkyl, aryloxy, aryloxy-C1-C6 alkyl, aryl-C1-C6 alkyloxy, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1-C6 alkyl, heteroaryloxy, heteroaryloxy-C1-C6 alkyl, heteroaryl-C1-C6 alkyloxy, heteroarylcarbonyl, heteroarylsulfonyl, heterocyclyl, heterocyclyl-C1-C6 alkyl, heterocyclyloxy, heterocyclooxy-C1-C6 alkyl, heterocyclyl-C1-C6 alkyloxy, heterocyclylcarbonyl, heterocyclylsulfonyl, aryl-NQ₂₁-(C1-C6)alkyl, heteroaryl-NQ₂₁-(C1-C6)alkyl, or heterocyclyl-NQ₂₁-(C1-C6)alkyl, wherein the last 35 groups as mentioned each are independently substituted by 0, 1, 2, or 3 groups selected from the group consisting of cyano, halogen, nitro, cyanothio, OQ₂₁, S(O)_pQ₂₂, N(Q₂₁)₂, NQ₂₁OQ₂₁, COQ₂₁, OCOQ₂₁, SCOQ₂₂, NQ₂₁COQ₂₁, NQ₂₁SO₂Q₂₂, CO₂Q₂₁, COSQ₂₁, CON(Q₂₁)₂, and C1-C6 alkoxy-C1-C6 alkoxycarbonyl;

Q₂₁ each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkyl-C1-C6 alkyl;

Q₂₂ each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkyl-C1-C6 alkyl;

p each independently represents 0, 1, or 2.

In addition, the derivatives also include salts commonly used in pesticides, for example, it can be processed into an metal salt, an amine salt, a sulfonium salt or a phosphonium salt; or, when a basic moiety is present in the molecule, it can be processed into, for example, a sulfate, a hydrochloride, a nitrate, a phosphate, etc. When these salts are used as herbicides in agriculture or horticulture, they are also included in the present invention. In the present invention, the “metal salt” may be, for example, an alkali metal salt, an alkaline earth metal salt, an aluminum salt or an iron salt; the “alkali metal salt” may be, for example, a sodium salt, a potassium salt or a lithium salt, preferably a sodium salt or a potassium salt. In the present invention, the “alkaline earth metal salt” may be, for example, a calcium salt or a magnesium salt, preferably a calcium salt. In the present invention, the “amine salt” may be, for example, a secondary alkylamine salt, a tertiary alkylamine salt or a quaternary alkylammonium salt; a primary alkanolamine salt, a secondary alkanolamine salt, a tertiary alkanolamine salt or a quaternary alkanoammonium salt; a primary alkylalkanolamine salt, a secondary alkylalkanolamine salt, a tertiary alkylalkanolamine salt or a quaternary alkylalkanolammonium salt; or a primary alkoxyalkanolamine salt, a secondary alkoxyalkanolamine salt, a tertiary alkoxyalkanolamine salt or a quaternary alkoxyalkanolammonium salt, preferably, wherein the alkyl, alkanol and alkoxy are independently saturated and independently contain 1-4 carbon atoms, and may also be substituted by phenyl and/or halogen, more preferably, ethanolamine salt, dimethylethanolamine salt, triethanolamine salt, dimethylamine salt, triethylamine salt, isopropylamine salt, choline salt, diglycolamine salt,

In the present invention, the “sulfonium salt” and “phosphonium salt” may be, for example, an alkylsulfonium salt, an alkylphosphonium salt or an alkanolphosphonium salt, preferably, wherein the alkyl is independently saturated and independently contain 1-4 carbon atoms, and may also be substituted by phenyl and/or halogen, more preferably,

Solvates of the compounds of the invention are also included in the invention.

Wherein, unless otherwise specified, the “heterocyclyl” of the present invention includes but not limited to,

which has 0, 1 or 2 oxo groups; the “aryl” includes but not limited to, phenyl, naphthyl,

the “heteroaryl” is an aromatic cyclic group having, for example, 3 to 6 ring atoms and optionally fused with a benzo ring, 1 to 4 (for example, 1, 2, 3 or 4) of the ring atoms are heteroatoms (for example, oxygen, nitrogen and/or sulfur). For example,

the above-mentioned groups are respectively unsubstituted or substituted by at least one group selected from: halogen, nitro, cyano, thiocyano, cyanoalkyl, mercapto, hydroxy, hydroxyalkyl, carboxyl, formyl, trialkylsilyl, dialkylphosphonyl; heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl, which is unsubstituted or substituted; alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkyl substituted by alkyl, OR″, SR″, -alkyl-OR″, —O-alkyl-OR″, -alkyl-SR″, COR″, -alkyl-COR″, —O-alkyl-COR″, COOR″, -alkyl-COOR″, —O-alkyl-COOR″, COSR″, SOR″, SO₂R″, —O—SO₂R″, -alkyl-SO₂R″, OCOR″, -alkyl-OCOR″, or SCOR″ group, which is with or without halogen; and amino, aminoalkyl, aminocarbonyl, aminocarbonylalkyl, or aminosulfonyl group which is unsubstituted or substituted by one or two groups selected from R″, COR″, COOR″, SO₂R″, and OR″, wherein the R″, COR″, COOR″, SO₂R″, or OR″ is with or without halogen; or, two adjacent substitutable positions of the above-mentioned “heterocyclyl”, “aryl”, “heteroaryl” groups are linked with —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O— or —CH═CH—CH═CH— group to form a ring, wherein the —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O— or —CH═CH—CH═CH— group is with or without halogen;

R″ each independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl; or heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl, which is unsubstituted or substituted.

Preferably, the above-mentioned groups are respectively unsubstituted or substituted by at least one group selected from: halogen, nitro, cyano, thiocyano, cyano C1-C6 alkyl, mercapto, hydroxy, hydroxy C1-C6 alkyl, carboxyl, formyl, tri(C1-C6 alkyl)silyl, di(C1-C6 alkyl)phosphonyl; heterocyclyl, heterocyclyl-C1-C6 alkyl, aryl, aryl-C1-C6 alkyl, heteroaryl, or heteroaryl-C1-C6 alkyl, which is unsubstituted or substituted; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, OR″, SR″, —(C1-C6 alkyl)-OR″, —O—(C1-C6 alkyl)-OR″, —(C1-C6 alkyl)-SR″, COR″, —(C1-C6 alkyl)-COR″, —O—(C1-C6 alkyl)-COR″, COOR″, —(C1-C6 alkyl)-COOR″, —O—(C1-C6 alkyl) —COOR″, COSR″, SOR″, SO₂R″, —O—SO₂R″, —(C1-C6 alkyl)-SO₂R″, OCOR″, —(C1-C6 alkyl) —OCOR″, or SCOR″, which is with or without halogen; and amino, amino-C1-C6 alkyl, aminocarbonyl, aminocarbonyl-C1-C6 alkyl, or aminosulfonyl group, which is unsubstituted or substituted by one or two groups selected from R″, COR″, COOR″, SO₂R″, and OR″, wherein the R″, COR″, COOR″, SO₂R″, or OR″ is with or without halogen; or, two adjacent substitutable positions of the above-mentioned “heterocyclyl”, “aryl”, “heteroaryl” groups are linked with —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O—, or —CH═CH—CH═CH— group to form a ring, wherein the —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O—, or —CH═CH—CH═CH— group is with or without halogen;

R″ each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkenyl; or heterocyclyl, heterocyclyl-C1-C6 alkyl, aryl, aryl-C1-C6 alkyl, heteroaryl, or heteroaryl-C1-C6 alkyl, which is unsubstituted or substituted.

More preferably, the “heterocyclyl” is

which has 0, 1, or 2 oxo groups; the “aryl” is phenyl, naphthyl,

the “heteroaryl” is

the above-mentioned groups are respectively unsubstituted or substituted by 1˜3 groups selected from: halogen, nitro, cyano, thiocyano, cyano C1-C6 alkyl, mercapto, hydroxy, hydroxy C1-C6 alkyl, carboxyl, formyl;

phenyl, or benzyl group, which is unsubstituted or substituted by 1˜3 groups selected from halogen, hydroxy, nitro, cyano, amino, carboxyl, C1-C6 alkyl with or without halogen, C2-C6 alkenyl with or without halogen, C2-C6 alkynyl with or without halogen, C3-C6 cycloalkyl with or without halogen, C1-C6 alkoxy with or without halogen, C1-C6 alkoxycarbonyl with or without halogen, C1-C6 alkylacyl with or without halogen, C1-C6 alkylacyloxy with or without halogen, C1-C6 alkylamino with or without halogen, and C1-C6 alkylsulfonyl with or without halogen; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, OR″, SR″, —(C1-C6) alkyl —OR″, —O—(C1-C6) alkyl —OR″, —(C1-C6) alkyl —SR″, COR″, —(C1-C6) alkyl —COR″, —O—(C1-C6) alkyl —COR″, COOR″, —(C1-C6) alkyl —COOR″, —O—(C1-C6) alkyl —COOR″, COSR″, SOR″, SO₂R″, —O—SO₂R″, —(C1-C6) alkyl —SO₂R″, OCOR″, —(C1-C6) alkyl —OCOR″, or SCOR″ group, which is with or without halogen; and amino, aminoalkyl, aminocarbonyl, or aminosulfonyl group, which is unsubstituted or substituted by one or two groups selected from R″, COR″, COOR″, SO₂R″, and OR″, wherein the R″, COR″, COOR″, SO₂R″, or OR″ is with or without halogen; or, two adjacent substitutable positions of the above-mentioned “heterocyclyl”, “aryl”, “heteroaryl” groups are linked with —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O—, or —CH═CH—CH═CH— group to form a ring, wherein the —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O—, or —CH═CH—CH═CH— group is with or without halogen;

R′ each independently represents hydrogen, nitro, hydroxy, amino; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkyl-C1-C6 alkyl,

C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C3-C6 cycloalkyloxy, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkoxy carbonyl, 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 alkyl)silyl, or di(C1-C6 alkyl)phosphonyl, which is with or without halogen; or phenyl, or benzyl which is unsubstituted or substituted by 1˜3 groups selected from halogen, hydroxy, nitro, cyano, amino, carboxyl, C1-C6 alkyl with or without halogen, C2-C6 alkenyl with or without halogen, C2-C6 alkynyl with or without halogen, C3-C6 cycloalkyl with or without halogen, C1-C6 alkoxy with or without halogen, C1-C6 alkoxy carbonyl with or without halogen, C1-C6 alkylacyl with or without halogen, C1-C6 alkylacyloxy with or without halogen, C1-C6 alkylamino with or without halogen, and C1-C6 alkylsulfonyl with or without halogen;

R″ each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkenyl; or

phenyl, or benzyl which is unsubstituted or substituted by 1˜3 groups selected from halogen, hydroxy, nitro, cyano, amino, carboxyl, C1-C6 alkyl with or without halogen, C2-C6 alkenyl with or without halogen, C2-C6 alkynyl with or without halogen, C3-C6 cycloalkyl with or without halogen, C1-C6 alkoxy with or without halogen, C1-C6 alkoxy carbonyl with or without halogen, C1-C6 alkylacyl with or without halogen, C1-C6 alkylacyloxy with or without halogen, C1-C6 alkylamino with or without halogen, and C1-C6 alkylsulfonyl with or without halogen.

In the definition of the compound represented by the above Formula and all of the following structural formulas, the technical terms used, whether used alone or used in compound word, represent the following substituents: an alkyl having more than two carbon atoms may be linear or branched. For example, the alkyl in the compound word “-alkyl-OR¹” may be —CH₂—, —CH₂CH₂—, —CH(CH₃)—, —C(CH₃)₂—, and the like. The alkyl is, for example, C₁ alkyl; methyl; C₂ alkyl; ethyl; C₃ alkyl; propyl such as n-propyl or isopropyl; C₄ alkyl; butyl such as n-butyl, isobutyl, tert-butyl or 2-butyl; C₅ alkyl; pentyl such as n-pentyl; C₆ alkyl; hexyl such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Similarly, the alkenyl is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, butyl-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl. The alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. The multiple bond(s) may be placed at any position of each unsaturated group. The cycloalkyl is a carbocyclic saturated ring system having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, the cycloalkenyl is monocycloalkenyl having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl, wherein double bond can be at any position. Halogen is fluorine, chlorine, bromine or iodine.

If a group is substituted by a group, which should be understood to mean that the group is substituted by one or more groups, which are same or different groups, selected from the mentioned groups. In addition, the same or different substitution characters contained in the same or different substituents are independently selected, and may be the same or different. This is also applicable to ring systems formed with different atoms and units. Meanwhile, the scope of the claims will exclude those compounds chemically unstable under standard conditions known to those skilled in the art.

In addition, unless specifically defined, the term occurring after multiple juxtaposed substituents (separated by “,” or “or”) in the present invention has a limiting effect on each of the substituents, such as the term “with or without halogen” in “alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, or cycloalkenylalkyl, which is with or without halogen” has a limiting effect on each of the following groups “alkyl”, “alkenyl”, “alkynyl”, “cycloalkyl”, “cycloalkenyl”, “cycloalkylalkyl” and “cycloalkenylalkyl”; a group (including heterocyclyl, aryl, heteroaryl, etc.) without being specified a linking site may be attached at any site, including a C or N site; if it is substituted, the substituent may be substituted at any site as long as it comply with the valence bond theory. For example, if the heteroaryl

is substituted with one methyl, it can be

etc.

Depending on the property of substituents and the linkage manner thereof, the compound of Formula I may exist as a stereoisomer. For example, if a compound has one or more asymmetric carbon atoms, it may has enantiomers and diastereomers. The stereoisomer can be obtained from the mixtures obtained in the preparation by conventional separation methods, for example by chromatographic separation. The stereoisomer may also be prepared selectively by using stereoselective reactions and using optically active starting materials and/or auxiliaries. The present invention also relates to all stereoisomers and mixtures thereof which are included in the general Formula I but are not specifically defined.

A method for preparing the 4-pyridinyl formamide compound I, which comprises the following steps:

subjecting the compound of the general formula II and the compound of the general formula III to amidation reaction to obtain the compound of the general formula I, the chemical reaction scheme is as follows:

The reaction is carried out in the presence of a halogenating agent, a catalyst and a solvent; preferably, the halogenating agent is SOCl₂, the catalyst is 4-dimethylaminopyridine, and the solvent is pyridine;

Or the reaction is carried out in the presence of a condensing agent and a solvent; preferably, the condensing agent is CDI, DCC, DBU or a combination thereof, and the solvent is methylene chloride.

The preparation method of its derivative 1-1 includes the following steps:

subjecting the compound of the general formula I and Hal-Q to reaction to obtain the compound of the general formula I-1, the chemical reaction scheme is as follows:

Wherein, Hal represents halogen, preferably fluorine, chlorine or bromine;

The reaction is carried out in the presence of a base and a solvent; preferably, the base is selected from one or a combination of potassium carbonate and sodium carbonate, and the solvent is one or more selected from the group consisting of DCM, DCE, ACN, THF, and DMF; or the reaction is carried out in the presence of a catalyst and a solvent; preferably, the catalyst is 4-dimethylaminopyridine, and the solvent is pyridine.

In addition, the compound of the general formula II and the compound of the general formula III are known in principle, and can be prepared, for example, by the methods described in WO199835967A2, CN103459386A, CN103987701A, WO2017055146A, WO2013017559A1, WO2012028579A1, WO2011035874A1. Moreover, the compounds of the present invention can also be prepared by referring to the methods described therein.

A herbicidal composition comprising (i) the 4-pyridinyl formamide compound or derivative thereof as shown in general formula I; preferably, further comprising (ii) one or more further herbicides and/or safeners; more preferably, further comprising (iii) agrochemically acceptable formulation auxiliaries.

A method for controlling a weed which comprises applying a herbicidally effective amount of at least one of the 4-pyridinyl formamide compound or derivative thereof or the herbicidal composition as above-described to a plant or a weed area.

Use of at least one of the 4-pyridinyl formamide compound or derivative thereof or the herbicidal composition as above-described for controlling a weed, preferably, wherein the 4-pyridinyl formamide compound or derivative thereof is used for preventing and/or controlling a weed in a useful crop, wherein the useful crop is a transgenic crop or a crop treated by gene editing technique.

The compounds of the formula I according to the invention have an outstanding herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. The active compounds also act efficiently on perennial weeds which produce shoots from rhizomes, root stocks or other perennial organs and which are difficult to control. In this context, it is generally immaterial whether the substances are applied pre-sowing, pre-emergence or post-emergence. Specifically, examples may be mentioned of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention, without these being a restriction to certain species. Examples of weed species on which the active compounds act efficiently are, from amongst the monocotyledons, Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria and also Cyperus species from the annual sector and from amongst the perennial species Agropyron, Cynodon, Imperata and Sorghum, and also perennial Cyperus species.

In the case of the dicotyledonous weed species, the spectrum of action extends to species such as, for example, Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Sida, Matricaria and Abutilon from amongst the annuals, and Convolvulus, Cirsium, Rumex and Artemisia in the case of the perennial weeds. The active compounds according to the invention also effect outstanding control of harmful plants which occur under the specific conditions of rice growing such as, for example, Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus. If the compounds according to the invention are applied to the soil surface prior to germination, then the weed seedlings are either prevented completely from emerging, or the weeds grow until they have reached the cotyledon stage but then their growth stops, and, eventually, after three to four weeks have elapsed, they die completely. In particular, the compounds according to the invention exhibit excellent activity against Apera spica venti, Chenopodium album, Lamium purpureum, Polygonum convulvulus, Stellaria media, Veronica hederifolia, Veronica persica, Viola tricolor and against Amaranthus, Galium and Kochia species.

Although the compounds according to the invention have an excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops such as, for example, wheat, barley, rye, rice, corn, sugarbeet, cohon and soya, are not damaged at all, or only to a negligible extent. In particular, they have excellent compatibility in cereals, such as wheat, barley and corn, in particular wheat. For these reasons, the present compounds are highly suitable for selectively controlling undesired plant growth in plantings for agricultural use or in plantings of ornamentals.

Owing to their herbicidal properties, these active compounds can also be employed for controlling harmful plants in crops of known or still to be developed genetically engineered plants. The transgenic plants generally have particularly advantageous properties, for example resistance to certain pesticides, in particular certain herbicides, resistance to plant diseases or causative organisms of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other particular properties relate, for example, to the quantity, quality, storage-stability, composition and to specific ingredients of the harvested product. Thus, transgenic plants having an increased starch content or a modified quality of the starch or those having a different fatty acid composition of the harvested produce are known.

The use of the compounds of the formula I according to the invention or their derivatives in economically important transgenic crops of useful and ornamental plants, for example of cereal, such as wheat, barley, rye, oats, millet, rice, maniok and corn, or else in crops of sugarbeet, cotton, soya, rapeseed, potato, tomato, pea and other vegetable species is preferred. The compounds of the formula I can preferably be used as herbicides in crops of useful plants which are resistant or which have been made resistant by genetic engineering toward the phytotoxic effects of the herbicides.

Conventional ways for preparing novel plants which have modified properties compared to known plants comprise, for example, traditional breeding methods and the generation of mutants. Alternatively, novel plants having modified properties can be generated with the aid of genetic engineering methods (see, for example, EP-A0 221 044, EP-A0 131 624). For example, there have been described several cases of:

• • genetically engineered changes in crop plants in order to modify the starch synthesized in the plants (for example WO 92/11376, WO 92/14827, WO 91/19806),
  • transgenic crop plants which are resistant to certain herbicides of the glufosinate- (cf., for example, EP-A 0 242 236, EP-A 0 242 246) or glyphosate-type (WO 92/00377), or of the sulfonylurea-type (EP-A0 257 993, U.S. Pat. No. 5,013,659A),
  • transgenic crop plants, for example cohon, having the ability to produce Bacillus thuringiensis toxins (Bt toxins) which impart resistance to certain pests to the plants (EP-A 0 142 924, EP-A0 193 259),
  • transgenic crop plants having a modified fatty acid composition (WO 91/13972).

Numerous molecular biological techniques which allow the preparation of novel transgenic plants having modified properties are known in principle; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.; or Winnacker “Gene und Klone” [Genes and Clones], VCH Weinheim, 2nd edition 1996, or Christou, “Trends in Plant Science” 1 (1996) 423-431). In order to carry out such genetic engineering manipulations, it is possible to introduce nucleic acid molecules into plasmids which allow a mutagenesis or a change in the sequence to occur by recombination of DNA sequences. Using the abovementioned standard processes it is possible, for example, to exchange bases, to remove partial sequences or to add natural or synthetic sequences. To link the DNA fragments with each other, it is possible to attach adaptors or linkers to the fragments.

Plant cells having a reduced activity of a gene product can be prepared, for example, by expressing at least one appropriate antisense-RNA, a sense-RNA to achieve a cosuppression effect, or by expressing at least one appropriately constructed ribozyme which specifically cleaves transcripts of the above-mentioned gene product.

To this end it is possible to employ both DNA molecules which comprise the entire coding sequence of a gene product including any flanking sequences that may be present, and DNA molecules which comprise only parts of the coding sequence, it being necessary for these parts to be long enough to cause an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product but which are not entirely identical.

When expressing nucleic acid molecules in plants, the synthesized protein can be localized in any desired compartment of the plant cells. However, to achieve localization in a certain compartment, it is, for example, possible to link the coding region with DNA sequences which ensure localization in a certain compartment. Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).

The transgenic plant cells can be regenerated to whole plants using known techniques. The transgenic plants can in principle be plants of any desired plant species, i.e. both monocotyledonous and dicotyledonous plants. In this manner, it is possible to obtain transgenic plants which have modified properties by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or by expression of heterologous (=foreign) genes or gene sequences.

When using the active compounds according to the invention in transgenic crops, in addition to the effects against harmful plants which can be observed in other crops, there are frequently effects which are specific for the application in the respective transgenic crop, for example a modified or specifically broadened spectrum of weeds which can be controlled, modified application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crops are resistant, and an effect on the growth and the yield of the transgenic crop plants. The invention therefore also provides for the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants.

In addition, the substances according to the invention have outstanding growth-regulating properties in crop plants. They engage in the plant metabolism in a regulating manner and can this be employed for the targeted control of plant constituents and for facilitating harvesting, for example by provoking desiccation and stunted growth. Furthermore, they are also suitable for generally regulating and inhibiting undesirable vegetative growth, without destroying the plants in the process. Inhibition of vegetative growth plays an important role in many monocotyledon and dicotyledon crops because lodging can be reduced hereby, or prevented completely.

The compounds according to the invention can be applied in the customary formulations in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules. The invention therefore also provides herbicidal compositions comprising compounds of the formula I. The compounds of the formula I can be formulated in various ways depending on the prevailing biological and/or chemico-physical parameters. Examples of suitable formulation options are: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil dispersions (OD), oil- or water-based dispersions, oil-miscible solutions, dusts (DP), capsule suspensions (CS), seed-dressing compositions, granules for broadcasting and soil application, granules (GR) in the form of microgranules, spray granules, coating granules and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes. These individual formulation types are known in principle and are described, for example, in Winnacker-Kiichler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th. Edition 1986; Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y., 1973; K. Martens, “Spray Drying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

The necessary formulation auxiliaries, such as inert materials, surfactants, solvents and other additives, are likewise known and are described, for example, in Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J., H. v. Olphen, “Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt, “Grenzfliichenaktive Athylenoxidaddkte” [Surface-active ethylene oxide adducts], Wiss. Verlagagesell. Stuttgart 1976; Winnacker-Kiichler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Edition 1986.

Wettable powders are preparations which are uniformly dispersible in water and which contain, in addition to the active compound and as well as a diluent or inert substance, surfactants of ionic and/or nonionic type (wetting agents, dispersants), for example polyethoxylated alkyl phenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines, fatty alcohol polyglycol ethersulfates, alkanesulfonates, alkylbenzenesulfonates, sodium ligninsulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutyinaphthalenesulfona-te or else sodium oleoylmethyltaurinate. To prepare the wettable powders, the herbicidally active compounds are finely ground, for example in customary apparatus such as hammer mills, fan mills and air-jet mills, and are mixed simultaneously or subsequently with the formulation auxiliaries.

Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else relatively high-boiling aromatic compounds or hydrocarbons or mixtures of the solvents, with the addition of one or more surfactants of ionic and/or nonionic type (emulsifiers). Examples of emulsifiers which can be used are calcium alkylarylsulfonates, such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters.

Dusts are obtained by grinding the active compound with finely divided solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth. Suspension concentrates can be water- or oil-based. They can be prepared, for example, by wet milling using commercially customary bead mills, with or without the addition of surfactants as already mentioned above, for example, in the case of the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be prepared for example by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and, if desired, surfactants as already mentioned above, for example, in the case of the other formulation types.

Granules can be prepared either by spraying the active compound onto adsorptive, granulated inert material or by applying active-compound concentrates to the surface of carriers such as sand, kaolinites or granulated inert material, by means of adhesive binders, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active compounds can also be granulated in the manner which is customary for the preparation of fertilizer granules, if desired as a mixture with fertilizers. Water-dispersible granules are generally prepared by the customary processes, such as spray-drying, fluidized-bed granulation, disk granulation, mixing using high-speed mixers, and extrusion without solid inert material.

For the preparation of disk, fluidized-bed, extruder and spray granules, see for example processes in “Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London; J. E. Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 ff; “Perry's Chemical Engineer's Handbook”, 5th Ed., McGraw-Hill, New York 1973, pp. 8-57. For further details on the formulation of crop protection products, see for example G. C. Klingman, “Weed Control as a Science”, John Wiley and Sons Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

The agrochemical formulations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of active compound of the formula F In wettable powders the concentration of active compound is, for example, from about 10 to 99% by weight, the remainder to 100% by weight consisting of customary formulation constituents. In emulsifiable concentrates the concentration of active compound can be from about 1 to 90%, preferably from 5 to 80%, by weight. Formulations in the form of dusts contain from 1 to 30% by weight of active compound, preferably most commonly from 5 to 20% by weight of active compound, while sprayable solutions contain from about 0.05 to 80%, preferably from 2 to 50%, by weight of active compound. In the case of water-dispersible granules the content of active compound depends partly on whether the active compound is in liquid or solid form and on the granulation auxiliaries, fillers, etc. that are used. In water-dispersible granules the content of active compound, for example, is between 1 and 95% by weight, preferably between 10 and 80% by weight.

In addition, the formulations of active compound may comprise the tackifiers, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, antifoams, evaporation inhibitors and pH and viscosity regulators which are customary in each case.

Based on these formulations it is also possible to produce combinations with other pesticidally active substances, for example insecticides, acaricides, herbicides and fungicides, and also with safeners, fertilizers and/or growth regulators, for example in the form of a ready-mix or tank mix.

Suitable active compounds which can be combined with the active compounds according to the invention in mixed formulations or in a tank mix are, for example, known active compounds as described in for example World Herbicide New Product Technology Handbook, China Agricultural Science and Farming Techniques Press, 2010.9 and in the literature cited therein. For example the following active compounds may be mentioned as herbicides which can be combined with the compounds of the formula I (note: the compounds are either named by the “common name” in accordance with the International Organization for Standardization (ISO) or by the chemical names, if appropriate together with a customary code number): acetochlor, butachlor, alachlor, propisochlor, metolachlor, s-metolachlor, pretilachlor, propachlor, ethachlor, napropamide, R-left handed napropamide, propanil, mefenacet, diphenamid, diflufenican, ethaprochlor, beflubutamid, bromobutide, dimethenamid, dimethenamid-P, etobenzanid, flufenacet, thenylchlor, metazachlor, isoxaben, flamprop-M-methyl, flamprop-M-propyl, allidochlor, pethoxamid, chloranocryl, cyprazine, mefluidide, monalide, delachlor, prynachlor, terbuchlor, xylachlor, dimethachlor, cisanilide, trimexachlor, clomeprop, propyzamide, pentanochlor, carbetamide, benzoylprop-ethyl, cyprazole, butenachlor, tebutam, benzipram, mogrton, dichlofluanid, naproanilide, diethatyl-ethyl, naptalam, flufenacet, EL-177, benzadox, chlorthiamid, chlorophthalimide, isocarbamide, picolinafen, atrazine, simazine, prometryn, cyanatryn, simetryn, ametryn, propazine, dipropetryn, SSH-108, terbutryn, terbuthylazine, triaziflam, cyprazine, proglinazine, trietazine, prometon, simetone, aziprotryne, desmetryn, dimethametryn, procyazine, mesoprazine, sebuthylazine, secbumeton, terbumeton, methoprotryne, cyanatryn, ipazine, chlorazine, atraton, pendimethalin, eglinazine, cyanuric acid, indaziflam, chlorsulfuron, metsulfuron-methyl, bensulfuron methyl, chlorimuron-ethyl, tribenuron-methyl, thifensulfuron-methyl, pyrazosulfuron-ethyl, mesosulfuron, iodosulfuron-methyl sodium, foramsulfuron, cinosulfuron, triasulfuron, sulfometuron methyl, nicosulfuron, ethametsulfuron-methyl, amidosulfuron, ethoxy sulfur on, cyclosulfamuron, rimsulfuron, azimsulfuron, flazasulfuron, monosulfuron, monosulfuron-ester, flucarbazone-sodium, flupyrsulfuron-methyl, halosulfuron-methyl, oxasulfuron, imazosulfuron, primisulfuron, propoxycarbazone, prosulfuron, sulfosulfuron, trifloxysulfuron, triflusulfuron-methyl, tritosulfuron, sodium metsulfuron methyl, flucetosulfuron, HNPC—C, orthosulfamuron, propyrisulfuron, metazosulfuron, acifluorfen, fomesafen, lactofen, fluoroglycofen, oxyfluorfen, chlomitrofen, aclonifen, ethoxyfen-ethyl, bifenox, nitrofluorfen, chlomethoxyfen, fluorodifen, fluoronitrofen, furyloxyfen, nitrofen, TOPE, DMNP, PPG1013, AKH-7088, halosafen, chlortoluron, isoproturon, linuron, diuron, dymron, fluometuron, benzthiazuron, methabenzthiazuron, cumyluron, ethidimuron, isouron, tebuthiuron, buturon, chlorbromuron, methyldymron, phenobenzuron, SK-85, metobromuron, metoxuron, afesin, monuron, siduron, fenuron, fluothiuron, neburon, chloroxuron, noruron, isonoruron, 3-cyclooctyl-1, thiazfluron, tebuthiuron, difenoxuron, parafluron, methylamine tribunil, karbutilate, trimeturon, dimefuron, monisouron, anisuron, methiuron, chloreturon, tetrafluron, phenmedipham, phenmedipham-ethyl, desmedipham, asulam, terbucarb, barban, propham, chlorpropham, rowmate, swep, chlorbufam, carboxazole, chlorprocarb, fenasulam, BCPC, CPPC, carbasulam, butylate, benthiocarb, vemolate, molinate, triallate, dimepiperate, esprocarb, pyributicarb, cycloate, avadex, EPTC, ethiolate, orbencarb, pebulate, prosulfocarb, tiocarbazil, CDEC, dimexano, isopobnate, methiobencarb, 2,4-D butyl ester, MCPA-Na, 2,4-D isooctyl ester, MCPA isooctyl ester, 2,4-D sodium salt, 2,4-D dimethyla mine salt, MCPA-thioethyl, MCPA, 2,4-D propionic acid, high 2,4-D propionic acid salt, 2,4-D butyric acid, MCPA propionic acid, MCPA propionic acid salt, MCPA butyric acid, 2,4,5-D, 2,4,5-D propionic acid, 2,4,5-D butyric acid, MCPA amine salt, dicamba, erbon, chlorfenac, saison, TBA, chloramben, methoxy-TBA, diclofop-methyl, fluazifop-butyl, fluazifop-p-butyl, haloxyfop-methyl, haloxyfop-P, quizalofop-ethyl, quizalofop-p-ethyl, fenoxaprop-ethy, fenoxaprop-p-ethyl, propaquizafop, cyhalofop-butyl, metamifop, clodinafop-propargyl, fenthiaprop-ethyl, chloroazifop-propynyl, poppenate-methyl, trifopsime, isoxapyrifop, paraquat, diquat, oryzalin, ethalfluralin, isopropalin, nitralin, profluralin, prodinamine, benfluralin, fluchloraline, dinitramina, dipropalin, chlomidine, methalpropalin, dinoprop, glyphosate, anilofos, glufosinate ammonium, amiprophos-methyl, sulphosate, piperophos, bialaphos-sodium, bensulide, butamifos, phocarb, 2,4-DEP, H-9201, zytron, imazapyr, imazethapyr, imazaquin, imazamox, imazamox ammonium salt, imazapic, imazamethabenz-methyl, fluroxypyr, fluroxypyr isooctyl ester, clopyralid, picloram, trichlopyr, dithiopyr, haloxydine, 3,5,6-trichloro-2-pyridinol, thiazopyr, fluridone, aminopyralid, diflufenzopyr, triclopyr-butotyl, Cliodinate, sethoxydim, clethodim, cycloxydim, alloxydim, clefoxydim, butroxydim, tralkoxydim, tepraloxydim, buthidazole, metribuzin, hexazinone, metamitron, ethiozin, ametridione, amibuzin, bromoxynil, bromoxynil octanoate, ioxynil octanoate, ioxynil, dichlobenil, diphenatrile, pyraclonil, chloroxynil, iodobonil, flumetsulam, florasulam, penoxsulam, metosulam, cloransulam-methyl, diclosulam, pyroxsulam, benfuresate, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, benzobicylon, mesotrione, sulcotrione, tembotrione, tefuryltrione, bicyclopyrone, ketodpiradox, isoxaflutole, clomazone, fenoxasulfone, methiozolin, fluazolate, pyraflufen-ethyl, pyrazolynate, difenzoquat, pyrazoxyfen, benzofenap, nipyraclofen, pyrasulfotole, topramezone, pyroxasulfone, cafenstrole, flupoxam, aminotriazole, amicarbazone, azafenidin, carfentrazone-ethyl, sulfentrazone, bencarbazone, benzfendizone, butafenacil, bromacil, isocil, lenacil, terbacil, flupropacil, cinidon-ethyl, flumiclorac-pentyl, flumioxazin, propyzamide, MK-129, flumezin, pentachlorophenol, dinoseb, dinoterb, dinoterb acetate, dinosam, DNOC, chloronitrophene, medinoterb acetate, dinofenate, oxadiargyl, oxadiazon, pentoxazone, Flufenacet, fluthiacet-methyl, fentrazamide, flufenpyr-ethyl, pyrazon, brompyrazon, metflurazon, kusakira, dimidazon, oxapyrazon, norflurazon, pyridafol, quinclorac, quinmerac, bentazone, pyridate, oxaziclomefone, benazolin, clomazone, cinmethylin, ZJ0702, pyribambenz-propyl, indanofan, sodium chlorate, dalapon, trichloroacetic acid, monochloroacetic acid, hexachloroacetone, flupropanate, cyperquat, bromofenoxim, epronaz, methazole, flurtamone, benfuresate, ethofumesate, tioclorim, chlorthal, fluorochloridone, tavron, acrolein, bentranil, tridiphane, chlorfenpropmethyl, thidiarizonaimin, phenisopham, busoxinone, methoxyphenone, saflufenacil, clacyfos, chloropon, alorac, diethamquat, etnipromid, iprymidam, ipfencarbazone, thiencarbazone-methyl, pyrimisulfan, chlorflurazole, tripropindan, sulglycapin, prosulfalin, cambendichlor, aminocyclopyrachlor, rodethanil, benoxacor, fenclorim, flurazole, fenchlorazole-ethyl, cloquintocet-mexyl, oxabetrinil, MG/91, cyometrinil, DKA-24, mefenpyr-diethyl, furilazole, fluxofenim, isoxadifen-ethyl, dichlormid, halauxifen-methyl, DOW florpyrauxifen, UBH-509, D489, LS 82-556, KPP-300, NC-324, NC-330, KH-218, DPX-N8189, SC-0744, DOWC0535, DK-8910, V-53482, PP-600, MBH-001, KIH-9201, ET-751, KIH-6127 and KIH-2023.

In the context of the present specification, if an abbreviation of a generic name of an active compound is used, it includes in each case all customary derivatives, such as esters and salts, as well as isomers, in particular optical isomers, especially one or more commercially available forms. If the generic name denotes an ester or a salt, it also includes in each case all other conventional derivatives, such as other esters and salts, free acids and neutral compounds, as well as isomers, in particular optical isomers, especially one or more commercially available forms. The chemical name given to a compound means at least one compound encompassed by the generic name, and generally the preferred compound. In the case of sulfonamides such as sulfonylurea, salts also include salts formed by the exchange of cations with hydrogen atoms in the sulfonamide group. For example, 2,4-D or 2,4-DB derivatives include but are not limited to: 2,4-D or 2,4-DB salt such as sodium salt, potassium salt, dimethylammonium salt, triethanolammonium salt, isopropylamine salt, choline, etc., and 2,4-D or 2,4-DB esters such as methyl ester, ethyl ester, butyl ester, isooctyl ester, etc.; 2-methyl-4-chloro derivatives include but are not limited to: 2-methyl-4-chloro sodium salt, -potassium salt, -dimethylammonium salt, -isopropylamine salt, etc., as well as 2-methyl-4-chloro methyl ester, -ethyl ester, -isooctyl ester, -thioethyl, etc.

For use, the formulations which are present in commercially available form are, if appropriate, diluted in the customary manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Products in the form of dusts, granules for soil application or broadcasting and sprayable solutions are usually not further diluted with other inert substances prior to use. The application rate of the compounds of the formula I required varies with the external conditions, such as temperature, humidity, the nature of the herbicide used and the like. It can vary within wide limits, for example between 0.001 and 1.0 kg a.i./ha or more of active substance, but it is preferably between 0.005 and 750 g a.i./ha, in particular between 0. 005 and 500 g a.i./ha.

SPECIFIC MODE FOR CARRYING OUT THE INVENTION

The following embodiments are used to illustrate the present invention in detail and should not be taken as any limit to the present invention. The scope of the invention would be explained through the Claims.

In view of economics and variety of a compound, we preferably synthesized several compounds, part of which are listed in the following Table A1. The structure and information of a certain compound are shown in Table A1. The compounds in Table A1 are listed for further explication of the present invention, other than any limit therefor. The subject of the present invention should not be interpreted by those skilled in the art as being limited to the following compounds.

TABLE A1
Structures and 1H NMR data of compounds
	I
NO.	X	Y	M	1HNMR
1-1	Cl	CH3		1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.52 (d, J = 5.5 Hz, 1H), 7.49 (d, J = 5.5 Hz, 1H), 4.25 (s, 3H), 2.50 (s, 3H).
1-2	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.47 (d, J = 5.5 Hz, 1H), 7.50 (d, J = 5.5 Hz, 1H), 4.25 (s, 3H), 1.54 (s, 9H).
1-3	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.45 (d, J = 5.5 Hz, 1H), 7.48 (d, J = 5.5 Hz, 1H), 4.25 (s, 3H), 2.62-2.57 (m, 1H), 1.03-0.94 (m, 2H), 0.95-0.85 (m, 2H).
1-4	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.48 ((d, J = 5.5 Hz, 1H), 7.49 (d, J = 5.5 Hz, 1H), 4.25 (s, 3H), 3.05-3.01 (m, 1H), 1.99-1.95 (m, 2H), 1.73-1.70 (m, 2H), 1.60-1.45 (m, 6H).
1-5	Cl			1H NMR (500 MHz, DMSO-d6) δ 11.98 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.63 (d, J = 5.0 Hz, 1H), 6.03 (t, J = 7.0 Hz, 1H), 4.00 (s, 3H), 2.35-2.10 (m, 4H), 1.74 (t, J = 6.0 Hz, 2H), 1.69-1.60 (m, 2H).
1-6	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.78 (d, J = 5.0 Hz, 1H), 7.23 (d, J = 5.0 Hz, 1H), 6.58- 6.53 (m, 1H), 4.32 (s, 3H), 3.55 (t, J = 5.5 Hz, 2H), 3.33 (dt, J = 6.5, 1.5 Hz, 2H), 3.20 (t, J = 5.5, 1.5 Hz, 2H), 1.47 (s, 9H).
1-7	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 7.38 (d, J = 5.0 Hz, 1H), 6.12-6.09 (m, 1H), 4.31 (s, 3H), 4.20-4.15 (m, 2H), 3.79 (t, J = 5.5 Hz, 2H), 2.16-2.10 (m, 2H).
1-8	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 7.77 (d, J = 5.50 Hz, 1H), 7.69-7.63 (m, 2H), 7.55-7.45 (m, 3H), 3.97 (s, 3H).
1-9	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 7.33-7.22 (m, 3H), 7.21 (d, J = 7.5 Hz, 1H), 3.99 (s, 3H), 2.07 (s, 3H).
1-10	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 7.89-7.83 (m, 1H), 7.81-7.71 (m, 2H), 7.59 (t, J = 7.5 Hz, 1H), 7.32-7.21 (m, 1H), 4.33 (s, 3H), 2.47 (d, J = 1.5 Hz, 3H).
1-11	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.02 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 7.57 (d, J = 8.0 Hz, 2H), 7.31 (d, J = 8.0 Hz, 2H), 4.00 (s, 3H), 2.37 (s, 3H).
1-12	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.78 (d, J = 5.0 Hz, 1H), 7.89-7.75 (m, 1H), 7.46-7.41 (m, 2H), 7.36-7.27 (m, 1H), 7.20 (d, J = 7.5 Hz, 1H), 4.01 (s, 3H), 3.33 (q, J = 7.5 Hz, 2H), 1.01 (t, J = 7.5 Hz, 3H).
1-13	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 7.58 (d, J = 8.0 Hz, 2H), 7.32 (d, J = 8.0 Hz, 2H), 3.98 (s, H), 2.62 (t, J = 8.0 Hz, 2H), 1.60-1.29 (m, 6H), 0.85 (t, J = 6.5 Hz, 3H).
1-14	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.78 (d, J = 5.0 Hz, 1H), 7.74-7.69 (m, 2H), 7.52-7.46 (m, 2H), 4.33 (s, 3H), 2.09-1.98 (m, 2H), 1.81-1.67 (m, 4H), 1.35-1.24 (m, 2H), 1.27-1.13 (m, 6H), 0.83 (t, J = 8.0 Hz, 3H).
1-15	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.10 (s, 1H), 8.80 (d, J = 4.5 Hz, 1H), 7.85 (d, J = 4.5 Hz, 1H), 7.63-7.55 (m, 1H), 7.51-7.46 (m, 1H), 7.40-7.31 (m, 2H), 3.99 (s, 3H).
1-16	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 7.87-7.79 (m, 1H), 7.72 (d, J = 5.0 Hz, 1H), 7.69-7.63 (m, 1H), 7.48-7.46 (m, 1H), 7.32-7.20 (m, 1H), 4.33 (s, 3H).
1-17	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 7.79-7.69 (m, 3H), 7.39-7.26 (m, 2H), 3.99 (s, 3H)
1-18	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.55 (d, J = 5.0 Hz, 1H), 7.85 (dd, J = 7.5, 2.5 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 7.52-7.43 (m, 2H), 7.41-7.37 (m, 1H), 4.26 (s, 3H).
1-19	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 8.02 (t, J = 2.0 Hz, 1H), 7.89-7.71 (m 2H), 7.68 (d, J = 5.0 Hz, 1H), 7.45 (t, J = 7.5 Hz, 1H), 4.33 (s, 3H).
1-20	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.78 (d, J = 5.0 Hz, 1H), 7.80 (d, J = 5.0 Hz, 1H), 7.70 (d, J = 8.0 Hz, 2H), 7.58 (d, J = 8.0 Hz, 2H), 4.00 (s, 3H).
1-21	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.56 (d, J = 5.5 Hz, 1H), 7.96 (t, J = 2.5 Hz, 1H), 7.88-7.86 (m, 1H), 7.61 (d, J = 5.5 Hz, 1H), 7.55-7.52 (m, 1H), 7.45 (t, J = 7.5 Hz, 1H), 4.25 (s, 3H).
1-22	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 7.72 (d, J = 8.0 Hz, 1H), 7.66-7.60 (m, 2H), 7.56-7.45 (m, 1H), 3.99 (s, 3H).
1-23	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.56 (d, J = 5.5 Hz, 1H), 8.06 (dd, J = 7.5, 2.0 Hz, 1H), 7.61 (d, J = 5.5 Hz, 1H), 7.39-7.36 (m, 1H), 7.35-7.29 (m, 2H), 4.73 (s, 2H), 4.25 (s, 3H).
1-24	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.57 (d, J = 5.0 Hz, 1H), 7.96-7.90 (m, 2H), 7.51 (d, J = 5.0 Hz, 1H), 7.3-7.26 (m, 2H), 4.40 (s, 2H), 4.25 (s, 3H).
1-25	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.57 (d, J = 5.5 Hz, 1H), 7.89-7.82 (m, 2H), 7.72-7.66 (m, 2H), 7.50 (d, J = 5.5 Hz, 1H), 4.26 (s, 3H).
1-26	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.01 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.06-7.94 (m, 2H), 7.88 (d, J = 8.0 Hz, 1H), 7.84 (s, 1H), 7.80-7.76 (m, 1H), 4.00 (s, 3H).
1-27	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 7.98-7.79 (m, 5H), 4.07 (s, 3H).
1-28	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 7.75 (d, J = 5.0 Hz, 1H), 7.50-7.42 (m, 1H), 7.26-7.19 (m, 1H), 7.14 (d, J = 8.5 Hz, 1H), 7.06 (t, J = 7.5 Hz, 1H), 3.98 (s, 3H), 3.74 (s, 3H).
1-29	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 7.68-7.57 (m, 1H), 7.33 (t, J = 7.5 Hz, 1H), 7.23 (t, J = 2.0 Hz, 1H), 6.89-6.81 (m, 1H), 4.33 (s, 3H), 3.80 (s, 3H).
1-30	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.02 (s, 1H), 8.73 (d, J = 4.5 Hz, 1H), 7.69 (d, J = 4.5 Hz, 1H), 7.66 (d, J = 8.5 Hz, 2H), 6.88 (d, J = 8.5 Hz, 2H) 3.99 (s, 3H), 3.81 (s, 3H)
1-31	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.13 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.85 (s, 1H), 7.70- 7.65 (m, 1H), 7.58-7.44 (m, 3H), 3.98 (s, 3H).
1-32	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.16 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 7.94 (d, J = 5.0 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.77-7.71 (m, 2H), 7.64 (d, J = 8.0 Hz, 1H), 4.11 (s, 3H).
1-33	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.78 (d, J = 4.5 Hz, 1H), 7.82-7.76 (m, 3H), 7.61- 7.35 (m, 2H), 4.00 (s, 3H).
1-34	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 9.74 (s, 1H), 8.54 (d, J = 5.5 Hz, 1H), 8.04 (dd, J = 7.5, 2.0 Hz, 1H), 7.49 (d, J = 5.5 Hz, 1H), 7.32-7.21 (m, 2H), 7.01 (dd, J = 7.5, 2.0 Hz, 1H), 4.25 (s, 3H).
1-35	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 9.63 (s, 1H), 8.71 (d, J = 4.5 Hz, 1H), 7.74-7.64 (m, 3H), 6.79-6.73 (m, 2H), 4.33 (s, 3H).
1-36	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 7.74 (d, J = 5.0 Hz, 1H), 7.60 (d, J = 7.5 Hz, 1H), 7.52 (d, J = 7.5 Hz, 1H), 7.48-7.35 (m, 2H), 5.28 (s, 1H), 4.56 (s, 2H), 3.98 (s, 3H).
1-37	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.71 (d, J = 4.5 Hz, 1H), 7.88-7.82 (m, 2H), 7.70 (d, J = 4.5 Hz, 1H), 6.58-6.52 (m, 2H), 6.27 (s, 2H), 4.33 (s, 3H).
1-38	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 8.10 (dd, J = 6.5, 2.5 Hz, 1H), 7.97 (dd, J = 7.0, 2.5 Hz, 1H), 7.66-7.62 (m, 2H), 7.22 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-39	Cl			1H NMR (500 MHz, DMSO-d6) δ 13.56 (s, 1H), 12.06 (s, 1H), 8.57 (d, J = 5.5 Hz, 1H), 8.07- 8.01 (m, 1H), 7.99-7.93 (m, 2H), 7.51 (d, J = 5.5 Hz, 1H), 4.26 (s, 3H).
1-40	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.80 (d, J = 5.0 Hz, 1H), 8.09 (d, J = 8.0 Hz, 2H), 7.82 (d, J = 8.0 Hz, 2H), 7.32 (d, J = 5.0 Hz, 1H), 4.00 (s, 3H), 3.88 (s, 3H).
1-41	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.80 (d, J = 5.0 Hz, 1H), 8.03 (d, J = 8.0 Hz, 2H), 7.78 (d, J = 8.0 Hz, 2H), 7.35 (d, J = 5.0 Hz, 1H), 4.00 (s, 3H), 1.56 (s, 9H).
1-42	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 7.81 (dd, J =7.5, 2.0 Hz, 1H), 7.45-7.34 (m, 2H), 7.23-7.18 (m, 1H), 7.10 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H), 2.35 (s, 3H).
1-43	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.57 (d, J = 5.5 Hz, 1H), 7.97-7.91 (m, 2H), 7.54-7.47 (m, 3H), 4.26 (s, 3H), 3.33 (hept, J = 6.5 Hz, 1H), 1.31 (d, J = 6.5 Hz, 6H).
1-44	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.79 (d, J = 4.5 Hz, 1H), 8.39 (t, J = 2.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.63 (t, J = 7.5 Hz, 1H), 7.28 (d, J = 4.5 Hz, 1H), 4.32 (s, 3H), 3.25 (s, 3H).
1-45	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.01 (d, J = 8.0 Hz, 2H), 7.93 (d, J = 8.0 Hz, 2H), 7.86 (d, J = 5.0 Hz, 1H), 3.98 (s, 3H), 3.18 (s, 3H).
1-46	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.86 (d, J = 5.0 Hz, 1H), 7.98 (d, J = 8.0 Hz, 2H), 7.91 (d, J = 8.0 Hz, 2H), 7.45 (d, J = 5.0 Hz, 1H), 4.03 (s, 3H), 3.73-3.64 (m, 4H), 2.95 (t, J = 4.5 Hz, 4H).
1-47	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 10.14 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 7.73- 7.67 (m, 3H), 7.66-7.61 (m, 2H), 3.98 (s, 3H), 2.06 (s, 3H).
1-48	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 11.36 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 7.86- 7.80 (m, 2H), 7.77-7.70 (m, 2H), 7.42 (t, J = 7.0 Hz, 1H), 6.48 (dd, J = 16.5, 10.0 Hz, 1H), 6.29-6.20 (m, 1H), 5.78 (dd, J = 16.5, 10.0 Hz, 1H), 4.33 (s, 3H).
1-49	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.12 (s, 1H), 7.99-7.90 (m, 2H), 7.84 (d, J = 5.0 Hz, 1H), 7.74 (t, J = 7.5 Hz, 1H), 3.99 (s, 3H).
1-50	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 8.00 (d, J = 8.0 Hz, 2H), 7.86 (d, J = 8.0 Hz, 2H), 7.46 (t, J = 5.0 Hz, 1H), 4.00 (s, 3H).
1-51	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.94 (d, J = 4.5 Hz, 1H), 7.70-7.64 (m, 2H), 7.35 (d, J = 4.5 Hz, 1H), 7.06-6.99 (m, 2H), 5.33 (t, J = 6.5 Hz, 1H), 4.33 (s, 3H), 3.83-3.81 (m, 1H), 3.52-3.49 (m, 1H), 2.11-1.99 (m, 1H), 1.89-1.77 (m, 2H), 1.61-1.40 (m, 3H).
1-52	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 8.00 (dd, J = 7.5, 2.0 Hz, 1H), 7.68-7.64 (m, 3H), 7.63-7.53 (m, 3H), 7.49-7.41 (m, 2H), 7.40-7.35 (m, 1H), 4.25 (s, 3H).
1-53	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.79 (dd, J = 5.0, 2.5 Hz, 1H), 7.92-7.67 (m, 7H), 7.51-7.47 (m, 2H), 7.42-7.34 (m, 1H), 4.00 (s, 3H).
1-54	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.10 (s, 1H), 8.93 (d, J = 5.0 Hz, 1H), 8.14-8.08 (m, 2H), 7.90-7.81 (m, 3H), 7.65-7.59 (m, 2H), 7.40- 7.35 (m, 2H), 4.33 (s, 3H), 2.77-2.67 (m, 2H), 1.19 (t, J = 8.0 Hz, 3H).
1-55	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.15 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 7.75 (d, J = 7.5 Hz, 1H), 7.46 (td, J = 7.5, 2.0 Hz, 1H), 7.38 (td, J = 7.5, 2.0 Hz, 1H), 7.36-7.28 (m, 2H), 4.32 (s, 3H).
1-56	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.02 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 7.78 (d, J = 5.0 Hz, 1H), 7.68-7.54 (m, 1H), 7.47-7.43 (m, 2H), 7.41 7.27 (m, 5H), 6.85-6.72 (m, 1H), 5.10 (s, 2H), 4.33 (s, 3H).
1-57	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.84 (d, J = 5.0 Hz, 1H), 8.24 (dd, J = 7.5, 2.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 7.52-7.48 (m, 1H), 7.43-7.33 (m, 3H), 7.32-7.28 (m, 1H), 7.14-7.10 (m, 1H), 7.09-7.04 (m, 2H), 4.33 (s, 3H).
1-58	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.51 (d, J = 5.5 Hz, 1H), 7.59 (d, J = 5.5 Hz, 1H), 7.31-7.23 (m, 3H), 4.25 (s, 3H), 2.38 (s, 6H).
1-59	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 7.77 (d, J = 7.5 Hz, 1H), 7.71 (d, J = 5.0 Hz, 1H), 7.13-7.05 (m, 2H), 4.33 (s, 3H), 2.43 (d, J = 1.0 Hz, 3H), 2.31 (s, 3H).
1-60	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.01 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 7.73 (s, 1H), 7.24 (s, 2H), 7.11 (d, J = 5.0 Hz, 1H), 3.99 (s, 3H), 2.33 (s, 6H).
1-61	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.74 (d, J = 5.5 Hz, 1H), 7.81-7.78 (m, 2H), 7.56 (d, J = 5.5 Hz, 1H), 7.49 (t J = 2.5 Hz, 1H), 4.26 (s, 3H), 1.31 (s, 18H).
1-62	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.50 (d, J = 5.5 Hz, 1H), 7.68-7.65 (m, 1H), 7.59 (d, J = 5.5 Hz, 1H), 7.40-7.27 (m, 2H), 4.26 (s, 3H).
1-63	Cl			1H NMR (500 MHz, DMSO-d6) δ 11.85 (s, 1H), 8.74 (d, J = 4.5 Hz, 1H), 7.64-7.58 (m, 1H), 7.39- 7.32 (m, 1H), 7.2-7.15 (m, 1H), 7.08 (d, J = 4.5 Hz, 1H), 4.31 (s, 3H).
1-64	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.10 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.86 (d, J = 5.0 Hz, 1H), 7.57-7.52 (m, 1H), 7.44 (t, J = 10.0 Hz, 1H), 7.26 (dd, J = 8.5, 7.0 Hz, 1H), 3.99 (s, 3H).
1-65	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.84 (d, J = 5.0 Hz, 1H), 7.40 (t, J = 9.0 Hz, 2H), 7.25-7.20 (m, 1H), 3.99 (s, 3H).
1-66	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.78 (d, J = 5.5 Hz, 1H), 7.86-7.70 (m, 2H), 7.66-7.49 (m, 2H), 4.00 (s, 3H),.
1-67	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.84 (d, J = 5.0 Hz, 1H), 7.29-7.19 (m, 3H), 3.99 (s, 3H), 2.34 (s, 3H).
1-68	Cl			1H NMR (500 MHz, DMSO-d6) δ 11.96 (s, 1H), 8.78 (d, J = 4.5 Hz, 1H), 7.54 (d, J = 8.5, 1H), 7.37 (dd, J = 7.5, 2.0 Hz, 1H), 7.26 (d, J = 4.5 Hz, 1H), 7.20-7.16 (m, 1H), 4.32 (s, 3H), 2.29 (s, 3H).
1-69	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 7.80 (s, 1H), 7.35 (t, J = 8.0 Hz, 1H), 7.17 (t, J = 10.5 Hz, 2H), 3.98 (s, 3H), 2.39 (s, 3H),.
1-70	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.51 (d, J = 5.5 Hz, 1H), 7.56 (d, J = 5.5 Hz, 1H), 7.42-7.38 (m, 1H), 7.13-7.10 (m, 1H), 6.82-6.80 (m, 1H), 4.26 (s, 3H), 3.85 (s, 3H).
1-71	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.48 (d, J = 5.5 Hz, 1H), 7.56-7.49 (m, 2H), 7.17 (t, J = 2.0 Hz, 1H), 6.80-6.75 (m, 1H), 4.26 (s, 3H), 3.80 (s, 3H).
1-72	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.10 (s, 1H), 8.79 (d, J = 4.5 Hz, 1H), 7.84 (d, J = 4.5 Hz, 1H), 7.34-7.19 (m, 2H), 6.98-6.95 (m, 1H), 3.99 (s, 3H), 3.88 (s, 3H).
1-73	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.55 (d, J = 5.5 Hz, 1H), 7.80 (dd, J = 8.5, 7.5 Hz, 1H), 7.60-7.50 (m, 2H), 7.23-7.20 (m, 1H), 4.25 (s, 3H).
1-74	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 7.77 (d, J = 7.5 Hz, 1H), 7.45-7.39 (m, 1H), 7.33-7.23 (m, 2H), 4.32 (s, 3H).
1-75	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.14 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 7.94-7.84 (m, 3H), 7.65-7.51 (m, 1H), 3.99 (s, 3H).
1-76	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.55 (d, J = 5.5 Hz, 1H), 8.05 (d, J = 8.5 Hz, 1H), 7.84 (d, J = 2.0 Hz, 1H), 7.74 (dd, J = 8.5, 2.0 Hz, 1H), 7.58 (d, J = 5.5 Hz, 1H), 4.26 (s, 3H).
1-77	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.19 (s, 1H), 8.97 (d, J = 5.0 Hz, 1H), 8.49 (s, 2H), 8.42 (s, 1H), 8.02 (d, J = 5.0 Hz, 1H), 4.12 (s, 3H).
1-78	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.69 (d, J = 5.5 Hz, 1H), 8.05-7.95 (m, 2H), 7.69 (d, J = 5.5 Hz, 1H), 7.51 (dd, J = 13.5, 2.5 Hz, 1H), 4.33 (s, 3H).
1-79	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.70 (d, J = 5.5 Hz, 1H), 7.96-7.89 (m, 2H), 7.76 (dd, J = 8.0, 7.0 Hz, 1H), 7.71 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H).
1-80	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.69 (d, J = 5.5 Hz, 1H), 8.12-8.08 (m, 1H), 7.82-7.78 (m, 1H), 7.69 (d, J = 5.5 Hz, 1H), 7.32 (dt, J = 7.5, 2.5 Hz, 1H), 4.33 (s, 3H).
1-81	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.70 (d, J = 5.5 Hz, 1H), 8.06-7.95 (m, 2H), 7.89 (t, J = 2.0 Hz, 1H), 7.70-7.68 (m, 1H), 4.33 (s, 3H).
1-82	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.69 (d, J = 5.5 Hz, 1H), 8.07 (dd, J = 7.5, 2.0 Hz, 1H), 7.77-7.73 (m, 1H), 7.70 (d, J = 5.5 Hz, 1H), 7.45 (dd, J = 11.5, 7.5 Hz, 1H), 4.33 (s, 3H).
1-83	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.70 (d, J = 5.5 Hz, 1H), 7.99-7.95 (m, 2H), 7.67 (d, J = 5.5 Hz, 1H), 7.49-7.45 (m, 1H), 4.33 (s, 3H).
1-84	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.69 (d, J = 5.5 Hz, 1H), 8.26-8.21 (m, 1H), 8.16 (dd, J = 8.0, 2.5 Hz, 1H), 7.70 (d, J = 5.5 Hz, 1H), 7.47 (dd, J = 13.5, 7.5 Hz, 1H), 4.33 (s, 3H).
1-85	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.17-8.01 (m, 2H), 7.84 (d, J = 7.5 Hz, 1H), 7.69-7.64 (m, 1H), 4.00 (s, 3H),.
1-86	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.90-7.85 (m, 1H), 7.81 (d, J = 2.0 Hz, 1H), 7.58 (dd, J = 8.5, 2.0 Hz, 1H), 7.48 (d, J = 8.5 Hz, 1H), 3.99 (s, 3H).
1-87	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.18 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 7.89 (d, J = 7.0 Hz, 1H), 7.84-7.77 (m, 1H), 7.58-7.51 (m, 1H), 7.44 (d, J = 7.0 Hz, 1H), 4.02 (s, 3H).
1-88	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.92 (d, J = 2.0 Hz, 1H), 7.85-7.77 (m, 2H), 7.70-7.67 (m, 1H), 4.00 (s, 3H).
1-89	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.79 (d, J = 4.5 Hz, 1H), 7.84 (d, J = 4.5 Hz, 1H), 7.78 (t, J = 2.0 Hz, 1H), 7.71 (d, J = 2.0 Hz, 2H), 3.99 (s, 3H).
1-90	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.79 (d, J = 4.5 Hz, 1H), 7.84 (d, J = 4.5 Hz, 1H), 7.62 (dt, J = 9.0, 2.0 Hz, 1H), 7.57 (s, 1H), 7.52 (d, J = 9.0 Hz, 1H), 3.99 (s, 3H).
1-91	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.82 (d, J = 9.0 Hz, 1H), 7.76-7.71 (m, 2H), 7.55 (d, J = 8.5 Hz, 1H), 3.99 (s, 3H).
1-92	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.87-7.81 (m, 2H), 7.68 (d, J = 5.0 Hz, 1H), 7.29-7.22 (m, 1H), 4.33 (s, 3H).
1-93	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.73-7.66 (m, 1H), 7.54- 7.42 (m, 1H), 7.48 (d, J = 5.0 Hz, 1H), 7.18 (t, J = 7.5 Hz, 1H), 4.33 (s, 3H).
1-94	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.14 (s, 1H), 8.78 (d, J = 5.0 Hz, 1H), 7.86 (d, J = 5.0 Hz, 1H), 7.64 (dd, J = 9.0, 2.5 Hz, 1H), 7.51 (dd, J = 8.5, 6.0 Hz, 1H), 7.38-7.30 (m, 1H), 3.98 (s, 3H).
1-95	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.10 (s, 1H), 8.80 (d, J = 5.0 Hz, 1H), 7.87 (d, J = 5.0 Hz, 1H), 7.69-7.62 (m, 1H), 7.55 (d, J = 8.0 Hz, 1H), 7.46 (dd, J = 8.0, 2.0 Hz, 1H), 3.99 (s, 3H).
1-96	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.10 (s, 1H), 8.62 (d, J = 5.5 Hz, 1H), 7.84 (d, J = 2.0 Hz, 1H), 7.71 (d, J = 8.5 Hz, 1H), 7.62 (d, J = 5.5 Hz, 1H), 7.55 (dd, J = 8.5, 2.0 Hz, 1H), 4.26 (s, 3H).
1-97	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.54 (d, J = 5.5 Hz, 1H), 7.84-7.80 (m, 1H), 7.65- 7.56 (m, 2H), 7.28-7.24 (m, 1H), 4.26 (s, 3H).
1-98	Cl			1H NMR (500 MHz, DMSO-d6) δ 11.99 (s, 1H), 8.75 (d, J = 4.5 Hz, 1H), 8.14 (d, J = 2.0 Hz, 1H), 7.79 (dd, J = 7.5, 2.0 Hz, 1H), 7.52 (d, J = 7.5 Hz, 1H), 7.09 (d, J = 4.5 Hz, 1H), 4.32 (s, 3H), 3.94 (s, 3H).
1-99	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.10 (s, 1H), 11.26 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.38 (d, J = 2.0 Hz, 1H), 8.02 (dd, J = 7.5, 2.0 Hz, 1H), 7.68 (d, J = 5.0 Hz, 1H), 7.09 (d, J = 7.5 Hz, 1H), 4.33 (s, 3H), 3.90 (s, 3H).
1-100	Cl			1H NMR (500 MHz, DMSO-d6) δ 13.19 (s, 1H), 12.01 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.70 (s, 1H), 8.66 (s, 1H), 7.88 (s, 1H), 7.63 (d, J = 4.5 Hz, 1H), 4.00 (s, 3H).
1-101	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.76 (d, J = 4.5 Hz, 1H), 7.81 (d, J = 7.5 Hz, 1H), 7.66-7.62 (m, 1H), 7.39 (dd, J = 7.5, 2.0 Hz, 1H), 7.24 (d, J = 4.5 Hz, 1H), 4.33 (s, 3H).
1-102	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.10 (s, 1H), 8.75 (d, J = 4.5 Hz, 1H), 7.81 (d, J = 4.5 Hz, 1H), 7.36-7.30 (m, 1H), 7.17 (d, J = 2.5 Hz, 1H), 7.07-7.01 (m, 1H), 3.98 (s, 3H), 3.83 (s, 3H).
1-103	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.20 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.69 (d, J = 5.0 Hz, 1H), 7.59 (d, J = 9.0 Hz, 1H), 7.23-7.15 (m, 1H), 7.05 (d, J = 3.0 Hz, 1H), 4.08 (s, 3H), 3.86 (s, 3H).
1-104	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 7.78 (d, J = 5.0 Hz, 1H), 7.16 (d, J = 8.5 Hz, 1H), 6.92 (d, J = 2.5 Hz, 1H), 6.88 (d, J = 8.5, 2.5 Hz, 1H), 4.01 (s, 3H), 3.81 (s, 3H), 2.09 (s, 3H).
1-105	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.71 (d, J = 5.0 Hz, 1H), 7.14 (d, J = 8.5 Hz, 1H), 6.70-6.59 (m, 2H), 3.97 (s, 3H), 3.81 (s, 3H), 3.73 (s, 3H).
1-106	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 7.81 (d, J = 5.0 Hz, 1H), 7.41-7.29 (m, 6H), 7.03-6.95 (m, 2H), 5.18 (s, 2H), 3.98 (s, 3H).
1-107	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 7.84-7.75 (m, 2H), 7.70 (dd, J = 7.5, 2.0 Hz, 1H), 7.50-7.44 (m, 2H), 7.42 (d, J = 7.5 Hz, 1H), 7.41-7.34 (m, 2H), 7.32-7.28 (m, 1H), 4.33 (s, 3H).
1-108	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.13 (d, J = 2.0 Hz, 2H), 7.96 (t, J = 2.0 Hz, 1H), 7.80 (d, J = 5.0 Hz, 1H), 7.73 (dd, J = 7.5, 2.0 Hz, 4H), 7.49 (t, J = 7.5 Hz, 4H), 7.43-7.35 (m, 2H), 4.33 (s, 3H).
1-109	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.79 (d, J = 4.5 Hz, 1H), 7.67-7.60 (m, 2H), 7.55-7.42 (m, 1H), 3.99 (s, 3H).
1-110	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 7.89 (d, J = 5.0 Hz, 1H), 7.48 (dd, J = 7.5, 1.5 Hz, 1H), 7.26 (t, J = 7.5 Hz, 1H), 4.00 (s, 3H), 3.92 (s, 3H).
1-111	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.19 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.04-7.98 (m, 2H), 7.87 (d, J = 5.0 Hz, 1H), 7.64 (t, J = 7.5 Hz, 1H), 7.53-7.42 (m, 3H), 7.36 (d, J = 8.5 Hz, 1H), 3.98 (s, 3H).
1-112	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.13-8.06 (m, 2H), 7.99 (d, J = 7.5 Hz, 1H), 7.82 (d, J = 5.0 Hz, 1H), 7.79- 7.73 (m, 2H), 7.62-7.56 (m, 2H), 4.01 (s, 3H).
1-113	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.91 (d, J = 5.5 Hz, 1H), 8.33 (dd, J = 7.5, 1.5 Hz, 1H), 8.22 (dd, J = 7.5, 1.5 Hz, 1H), 8.03-7.99 (m, 1H), 7.84 (d, J = 5.5 Hz, 1H), 7.53-7.50 (m, 1H), 7.37 (dd, J = 7.5, 8.0 Hz, 1H), 6.63-6.60 (m, 1H), 4.33 (s, 3H).
1-114	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 9.28 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.60 (d, J = 7.5 Hz, 1H), 8.18-8.10 (m, 2H), 7.88-7.78 (m, 3H), 4.33 (s, 3H).
1-115	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.94-8.86 (m, 2H), 8.78 (d, J = 5.5 Hz, 1H), 8.38 (s, 1H), 8.05-7.95 (m, 2H), 7.86 (d, J = 5.0 Hz, 1H), 7.74-7.61 (m, 4H), 4.33 (s, 3H).
1-116	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.17 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.30 (d d, J = 7.5, 1.5 Hz, 1H), 8.22 (d, J = 7.5 Hz, 1H), 7.92 (d, J = 5.0 Hz, 1H), 7.68 (d, J = 8.0 Hz, 1H), 7.64-7.58 (m, 1H), 7.59-7.49 (m, 2H), 7.43 (t, J = 7.5 Hz, 1H), 4.01 (s, 3H).
1-117	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.01 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.13 (d, J = 1.5 Hz, 1H), 8.09-8.01 (m, 2H), 7.95 (dd, J = 7.5, 1.5 Hz, 1H), 7.81 (d, J = 5.0 Hz, 1H), 7.54 (dd, J = 7.5, 1.5 Hz, 1H), 7.48-7.41 (m, 1H), 7.37-7.32 (m, 1H), 4.33 (s, 3H).
1-118	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 8.51-8.38 (m, 3H), 7.98 (d, J = 5.0 Hz, 1H), 7.74 (s, 2H), 7.67-7.64 (m, 1H), 7.52 (s, 1H), 3.88 (s, 3H).
1-119	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.69 (d, J = 5.5 Hz, 1H), 8.63 (d, J = 5.5 Hz, 1H), 8.22 (dd, J = 8.0, 2.0 Hz, 1H), 7.82 (t, J = 8.0 Hz, 1H), 7.69 (d, J = 5.5 Hz, 1H), 7.41-7.38 (m, 1H), 4.25 (s, 3H).
1-120	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.89 (d, J = 7.5, 1H), 8.75 (d, J = 5.5 Hz, 1H), 7.92 (t, J = 7.5 Hz, 1H), 7.82 (d, J = 5.5 Hz, 1H), 7.65 (d, J = 7.5 Hz, 1H), 4.33 (s, 3H).
1-121	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 9.11 (s, 1H), 8.75 (d, J = 5.5 Hz, 1H), 8.54 (d, J = 8.0 Hz, 1H), 8.19 (d, J = 8.0 Hz, 1H), 7.83 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H).
1-122	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.80 (d, J = 5.5 Hz, 1H), 8.71 (d, J = 5.5 Hz, 1H), 8.56 (s, 1H), 7.78 (d, J = 5.5 Hz, 1H), 7.53 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H).
1-123	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.76 (d, J = 5.5 Hz, 1H), 8.68 (dd, J = 8.0, 2.5 Hz, 1H), 8.22 (dd, J = 12.5, 2.5 Hz, 1H), 7.80 (d, J = 5.5 Hz, 1H), 7.62-7.58 (m, 1H), 4.33 (s, 3H).
1-124	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.86 (d, J = 2.5 Hz, 1H), 8.82 (d, J = 5.0 Hz, 1H), 8.69-8.68 (m, 1H), 8.11 (d, J = 8.0 Hz, 1H), 7.84 (d, J = 5.0 Hz, 1H), 7.57-7.55 (m, 1H), 4.00 (s, 3H).
1-125	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.56-8.49 (m, 1H), 8.48 (d, J = 5.0 Hz, 1H), 8.35 (s, 1H), 7.49 (d, J = 5.0 Hz, 1H), 7.36 (d, J = 5.0 Hz, 1H), 3.68 (s, 3H), 2.10 (s, 3H).
1-126	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.80 (d, J = 5.0 Hz, 1H), 8.65 (s, 1H), 8.52 (s, 1H), 7.90 (s, 1H), 7.81 (d, J = 5.0 Hz, 1H), 3.99 (s, 3H), 2.38 (s, 3H).
1-127	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.27 (dd, J = 5.5, 1.5 Hz, 1H), 8.18-8.16 (m, 1H), 7.78-7.75 (m, 1H), 7.72 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-128	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.77-8.71 (m, 2H), 8.40-8.36 (m, 2H), 7.88 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-129	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.80 (d, J = 4.5 Hz, 1H), 8.72 (d, J = 2.5 Hz, 1H), 8.20-8.18 (m, 1H), 7.82 (d, J = 4.5 Hz, 1H), 7.69 (d, J = 8.0 Hz, 1H), 3.97 (s, 3H).
1-130	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.35 (dd, J = 5.0, 2.0 Hz, 1H), 8.07-8.02 (m, 1H), 7.92-7.85 (m, 2H), 4.33 (s, 3H).
1-131	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.81 (d, J = 1.5 Hz, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.02 (dd, J = 8.0, 1.5 Hz, 1H), 7.88 (d, J = 5.0 Hz, 1H), 7.76 (d, J = 8.0 Hz, 1H), 4.33 (s, 3H).
1-132	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.83 (d, J = 5.5 Hz, 1H), 8.75 (d, J = 7.5 Hz, 1H), 8.18 (dd, J = 7.5, 7.5 Hz, 1H), 7.98 (d, J = 5.5 Hz, 1H), 7.18 (dd, J = 12.5, 7.5 Hz, 1H), 4.33 (s, 3H).
1-133	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 9.25 (s, 1H), 9.08 (s, 1H), 8.85 (d, J = 5.5 Hz, 1H), 8.68 (s, 1H), 8.00 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H).
1-134	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.98 (s, 1H), 8.85 (d, J = 5.5 Hz, 1H), 8.24 (d, J = 8.0 Hz, 1H), 7.99 (d, J = 5.5 Hz, 1H), 7.87 (d, J = 8.0 Hz, 1H), 4.33 (s, 3H).
1-135	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.38-8.33 (m, 1H), 7.88 (d, J = 5.0 Hz, 1H), 7.16-7.11 (m, 1H), 4.33 (s, 3H).
1-136	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.14 (s, 1H), 7.87 (d, J = 5.0 Hz, 1H), 7.26 (d, J = 6.0 Hz, 1H), 3.99 (s, 3H), 2.17 (s, 3H).
1-137	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.02 (s, 1H), 8.85 (d, J = 4.5 Hz, 1H), 8.28 (dd, J = 11.0, 8.0 Hz, 1H), 7.52 (d, J = 4.5 Hz, 1H), 6.88 (dd, J = 8.0, 7.0 Hz, 1H), 4.32 (s, 3H), 2.79 (s, 3H).
1-138	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.88-8.82 (m, 2H), 7.54-7.47 (m, 2H), 4.32 (s, 3H), 2.37 (s, 3H).
1-139	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.84 (d, J = 4.5 Hz, 1H), 8.36 (d, J = 8.0 Hz, 1H), 7.47 (d, J = 8.0 Hz, 1H), 7.33 (d, J = 4.5 Hz, 1H), 4.32 (s, 3H).
1-140	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.18 (dd, J = 8.0, 6.0 Hz, 1H), 7.88 (d, J = 5.0 Hz, 1H), 7.74 (d, J = 8.0 Hz, 1H), 4.33 (s, 3H).
1-141	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.86 (d, J = 4.5 Hz, 1H), 8.69 (dd, J = 5.0, 1.5 Hz, 1H), 8.26 (dd, J = 8.0, 1.5 Hz, 1H), 7.67 (dd, J = 8.0, 5.0 Hz, 1H), 7.36 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-142	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.10 (s, 1H), 9.07 (d, J = 2.0 Hz, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.46-8.38 (m, 1H), 8.09 (d, J = 8.0 Hz, 1H), 7.91 (d, J = 5.0 Hz, 1H), 4.00 (s, 3H).
1-143	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.19 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.63 (d, J = 2.5 Hz, 1H), 8.21-8.08 (m, 1H), 7.88 (d J = 5.0 Hz, 1H), 7.08 (d, J = 8.5 Hz, 1H), 4.11 (s, 3H), 4.03 (s, 3H).
1-144	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 8.59 (d, J = 1.5 Hz, 1H), 8.03 (dd, J = 8.0, 1.5 Hz, 1H), 7.92 (d, J = 5.0 Hz, 1H), 7.09 (d, J = 8.0 Hz, 1H), 4.33 (q, J = 8.0 Hz, 2H), 4.33 (s, 3H), 1.28 (t, J = 8.0 Hz, 3H).
1-145	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.84 (d, J = 4.5 Hz, 1H), 8.38 (d, J = 1.5 Hz, 1H), 8.04-7.95 (m, 2H), 7.46 (t, J = 1.5 Hz, 1H), 6.18 (s, 2H), 4.33 (s, 3H).
1-146	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.14 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 8.53 (d, J = 2.5 Hz, 1H), 8.01 (dd, J = 9.0, 2.5 Hz, 1H), 7.74 (d, J = 5.0 Hz, 1H), 7.03 (d, J = 9.0 Hz, 1H), 4.03 (s, 3H), 3.73 (t, J = 5.0 Hz, 4H), 3.60 (t, J = 5.0 Hz, 4H).
1-147	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 8.66 (d, J = 5.0 Hz, 2H), 8.04 (d, J = 5.0 Hz, 1H), 7.90 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-148	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.85 (d, J = 5.5 Hz, 1H), 8.78 (d, J = 5.5 Hz, 1H), 8.53 (s, 1H), 8.29 (d, J = 5.5 Hz, 1H), 8.00 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H).
1-149	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.27 (d, J = 5.0 Hz, 1H), 8.06-7.97 (m, 2H), 7.84 (dd, J = 5.0, 1.0 Hz, 1H), 4.33 (s, 3H).
1-150	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.41 (d, J = 8.0 Hz, 1H), 8.33 (d, J = 4.5 Hz, 1H), 7.73 (dd, J = 8.0, 4.5 Hz, 1H), 7.51 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H).
1-151	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.42-8.34 (m, 2H), 8.06-7.96 (m, 2H), 4.33 (s, 3H).
1-152	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.86 (d, J = 5.0 Hz, 1H), 8.40 (d, J = 5.0 Hz, 1H), 7.94 (d, J = 5.0 Hz, 1H), 7.51 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H).
1-153	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 8.49 (s, 2H), 8.11 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-154	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.94 (dd, J = 7.5, 7.5 Hz, 1H), 8.89 (d, J = 5.5 Hz, 1H), 8.01 (d, J = 5.5 Hz, 1H), 7.68 (dd, J = 12.0, 7.5 Hz, 1H), 4.33 (s, 3H).
1-155	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.94 (d, J = 7.5 Hz, 1H), 8.89 (d, J = 5.5 Hz, 1H), 8.34 (d, J = 7.5 Hz, 1H), 8.01 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H).
1-156	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.10 (s, 1H), 9.40 (s, 2H), 9.35 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.89 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-157	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 9.27 (s, 2H), 8.79 (d, J = 5.0 Hz, 1H), 8.08 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-158	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 9.45 (d, J = 7.5 Hz, 2H), 8.89 (d, J = 5.5 Hz, 1H), 7.98 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H).
1-159	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 9.01 (s, 2H), 8.90 (d, J = 5.5 Hz, 1H), 7.96 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H).
1-160	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.63 (s, 2H), 7.70 (d, J = 5.0 Hz, 1H), 7.11 (s, 2H), 4.00 (s, 3H).
1-161	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 9.50 (s, 2H), 8.89 (d, J = 5.0 Hz, 1H), 7.96 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.85 (s, 3H).
1-162	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.34 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.74 (s, 1H), 7.31 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H), 3.98 (s, 3H), 3.84 (s, 3H).
1-163	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 9.25 (s, 2H), 8.86 (d, J = 5.5 Hz, 1H), 8.00 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H).
1-164	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.88 (d, J = 5.5 Hz, 1H), 8.84 (d, J = 12.5, 2.5 Hz, 2H), 7.99 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H).
1-165	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 9.10 (d, J = 5.0 Hz, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 5.0 Hz, 1H), 8.02 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-166	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.98 (d, J = 5.0 Hz, 1H), 7.95 (d, J = 5.0 Hz, 1H), 7.50 (d, J = 12.5 Hz, 2H), 4.33 (s, 3H).
1-167	Cl			1H NMR (500 MHz, DMSO-d6) δ 13.15 (s, 1H), 8.38 (d, J = 5.0 Hz, 1H), 8.22 (s, 2H), 7.16 (d, J = 5.0 Hz, 1H), 3.70 (s, 3H).
1-168	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.15 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 8.63 (s, 1H), 8.25 (s, 1H), 7.68 (d, J = 5.0 Hz, 1H), 4.12 (s, 3H), 4.03 (s, 3H).
1-169	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.01 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.20 (s, 1H), 7.59 (d, J = 5.0 Hz, 1H), 3.99 (s, 3H), 3.82 (s, 3H), 2.28 (s, 3H).
1-170	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.99 (d, J = 5.0 Hz, 1H), 7.67 (s, 1H), 7.52 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.94 (s, 3H), 2.34 (s, 3H).
1-171	Cl			1H NMR (500 MHz, DMSO-d6) δ 13.53 (s, 1H), 12.03 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 7.95 (d, J = 5.0 Hz, 1H), 7.40 (s, 1H), 4.33 (s, 3H), 2.31 (s, 3H).
1-172	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.02 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 8.53 (s, 1H), 8.15 (s, 1H), 7.56 (d, J = 5.0 Hz, 1H), 4.21-4.15 (m, 2H), 4.00 (s, 3H), 1.40 (t, J = 7.0 Hz, 3H).
1-173	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.17 (s, 1H), 8.97 (d, J = 5.0 Hz, 1H), 7.86 (d, J = 1.5 Hz, 1H), 7.47 (d, J = 5.0 Hz, 1H), 6.91 (d, J = 1.5 Hz, 1H), 4.33 (s, 3H), 4.20 (t, J = 8.0 Hz, 2H), 2.00 (m, 2H), 0.95 (t, J = 8.0 Hz, 3H).
1-174	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.91 (d, J = 5.5 Hz, 1H), 7.95 (t, J = 65.0 Hz, 1H), 7.71 (d, J = 5.5 Hz, 1H), 7.67 (s, 1H), 7.06 (s, 1H)), 4.33 (s, 3H).
1-175	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.13 (s, 1H), 8.95-8.69 (m, 2H), 8.30 (d, J = 5.5 Hz, 1H), 7.68 (s, 1H), 7.42-7.29 (m, 5H), 5.53 (s, 2H), 4.11 (s, 3H).
1-176	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.66-8.59 (m, 2H), 8.22 (s, 1H), 7.60 (d, J = 5.5 Hz, 1H), 5.65-5.60 (m, 1H), 4.00 (s, 3H), 3.51- 3.41 (m, 2H), 1.63 (d, J = 6.0 Hz, 3H), 1.06-0.97 (m, 3H).
1-177	Cl			1H NMR (500 MHz, DMSO-d6) δ 13.56 (s, 1H), 12.13 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 8.30 (d, J = 2.5 Hz, 1H), 7.89 (d, J = 2.5 Hz, 1H), 7.61 (d, J = 5.0 Hz, 1H), 4.00 (s, 3H).
1-178	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 7.84 (d, J = 2.5 Hz, 1H), 7.61-7.44 (m, 1H), 6.67 (d, J = 5.0 Hz, 1H), 3.99 (s, 3H), 3.83 (s, 3H).
1-179	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.98 (d, J = 4.5 Hz, 1H), 7.51 (d, J = 4.5 Hz, 1H), 6.55 (s, 1H), 4.33 (s, 3H), 4.00 (s, 3H), 2.35 (s, 3H).
1-180	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.98 (d, J = 5.0 Hz, 1H), 7.51 (d, J = 5.0 Hz, 1H), 6.68 (s, 1H), 4.33 (s, 3H), 4.02 (s, 3H).
1-181	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.96-7.73 (t, J = 6.5 Hz, 1H), 7.70 (d, J = 5.0 Hz, 1H), 7.64 (d, J = 2.5 Hz, 1H), 6.73 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H).
1-182	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 8.10 (d, J = 5.0 Hz, 1H), 7.61 (d, J = 2.5 Hz, 1H), 6.68 (d, J = 2.5 Hz, 1H), 6.12 (t, J = 6.5 Hz, 1H), 4.33 (s, 3H), 3.90-3.77 (m, 2H), 2.47-2.36 (m, 1H), 2.08- 1.95 (m, 2H), 1.81-1.69 (m, 1H), 1.59-1.55 (m, 2H).
1-183	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.16 (s, 1H), 8.84 (d, J = 5.0 Hz, 1H), 8.66 (s, 1H), 7.98-7.88 (m, 1H), 7.78 (d, J = 2.0 Hz, 1H), 7.25 (d, J = 2.0 Hz, 1H), 4.20 (s, 3H).
1-184	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.10-8.04 (m, 2H), 7.25 (d, J = 2.5 Hz, 1H), 6.98 (t, J = 2.5 Hz, 1H), 4.33 (s, 3H).
1-185	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 9.25 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.08 (d, J = 5.0 Hz, 1H), 7.29 (d, J = 2.5 Hz, 1H), 7.22 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H).
1-186	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.20 (dd, J = 3.0, 1.5 Hz, 1H), 7.74-7.58 (m, 3H), 4.01 (s, 3H).
1-187	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.93 (d, J = 2.5 Hz, 1H), 7.61 (d, J = 5.0 Hz, 1H), 6.92 (d, J = 2.5 Hz, 1H), 4.00 (s, 3H), 2.38 (s, 3H).
1-188	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.97 (s, 1H), 7.67 (d, J = 5.0 Hz, 1H), 7.42 (s, 1H), 4.03 (s, 3H), 2.29 (s, 3H).
1-189	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.99 (d, J = 5.0 Hz, 1H), 7.53 (d, J = 5.0 Hz, 1H), 7.33 (d, J = 2.5 Hz, 1H), 7.08 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H).
1-190	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 9.87 (s, 1H), 8.90 (d, J = 5.0 Hz, 1H), 8.10 (d, J = 5.0 Hz, 1H), 7.95 (d, J = 2.5 Hz, 1H), 7.81 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H).
1-191	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.11 (d, J = 2.5 Hz, 1H), 7.82 (d, J = 2.5 Hz, 1H), 7.77 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 2.50 (s, 3H).
1-192	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.92 (d, J = 5.0 Hz, 1H), 7.59-7.51 (m, 2H), 4.33 (s, 3H), 4.26 (s, 1H).
1-193	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.91 (d, J = 5.5 Hz, 1H), 8.45 (s, 1H), 8.09 (s, 1H), 7.91 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H).
1-194	CH3			1H NMR (500 MHz, DMSO-d6) δ 12.31 (s, 1H), 8.69 (d, J = 4.5 Hz, 1H), 7.60-7.52 (m, 2H), 7.14-7.03 (m, 3H), 4.33 (s, 3H), 2.35 (s, 3H).
1-195	F			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.44 (dd, J = 5.0, 1.5 Hz, 1H), 8.08-8.01 (m, 2H), 7.83 (dd, J = 7.5, 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.33 (s, 3H).
1-196	Br			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.80 (d, J = 5.5 Hz, 1H), 7.96 (dd, J = 7.5, 7.0 Hz, 2H), 7.72 (d, J = 5.5 Hz, 1H), 7.33 (dd, J = 12.0, 7.0 Hz, 2H), 4.33 (s, 3H).
1-197				1H NMR (500 MHz, DMSO-d6) δ 12.17 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.54-7.45 (m, 2H), 7.11-7.03 (m, 2H), 7.00 (d, J = 5.0 Hz, 1H), 4.35 (s, 3H), 3.16-3.11 (m, 1H), 1.25 (d, J = 6.5 Hz, 6H).
1-198	CF3			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.87 (d, J = 4.5 Hz, 1H), 7.64-7.56 (m, 2H), 7.13 (d, J = 4.5 Hz, 1H), 7.11-7.03 (m, 2H), 4.35 (s, 3H).
1-199				1H NMR (500 MHz, DMSO-d6) δ 11.98 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 7.61-7.53 (m, 4H), 7.42 (t, J = 7.5 Hz, 1H), 7.40 (d, J = 7.5 Hz, 1H), 7.37-7.29 (m, 2H), 7.11-7.03 (m, 2H), 4.29 (s, 3H).
1-200				1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 7.71-7.63 (m, 2H), 7.46 (d, J = 5.0 Hz, 1H), 7.11-7.03 (m, 2H) 4.34 (s, 3H), 3.79 (s, 3H).
1-201				1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 7.71-7.64 (m, 2H), 7.46 (d, J = 5.0 Hz, 1H), 7.11-7.03 (m, 2H), 4.34-4.06 (m, 2H), 4.34 (s, 3H), 1.61 (t, J = 8.0 Hz, 3H).
1-202				1H NMR (500 MHz, DMSO-d6) δ 11.93 (s, 1H), 8.67 (d, J = 4.5 Hz, 1H), 7.72-7.64 (m, 2H), 7.42 (d, J = 4.5 Hz, 1H), 7.11-7.03 (m, 2H), 4.46-4.39 (m, 2H), 4.34 (s, 3H).
1-203				1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.60 (d, J = 5.5 Hz, 1H), 8.02 (dd, J = 7.5, 7.5 Hz, 2H), 7.60 (d, J = 5.5 Hz, 1H), 7.32 (dd, J = 11.5, 7.5 Hz, 2H), 4.33 (s, 3H), 2.21 (s, 3H).
1-204				1H NMR (500 MHz, DMSO-d6) δ 11.82 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.64-7.56 (m, 2H), 7.24 (d, J = 5.0 Hz, 1H), 7.11-7.03 (m, 2H), 4.33 (s, 3H), 2.97-2.89 (m, 2H), 1.28 (t, J = 8.0 Hz, 3H).
1-205				1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.87 (d, J = 5.5 Hz, 1H), 7.98 (dd, J = 7.5, 7.5 Hz, 2H), 7.65 (d, J = 5.5 Hz, 1H), 7.33 (dd, J = 11.5, 7.5 Hz, 2H), 4.33 (s, 3H), 2.61 (s, 3H).
1-206				1H NMR (500 MHz, DMSO-6) δ 12.02 (s, 1H), 8.90 (d, J = 5.0 Hz, 1H), 7.66-7.59 (m, 2H), 7.28 (d, J = 5.0 Hz, 1H), 7.11-7.03 (m, 2H), 4.30 (s, 3H), 3.25-3.16 (m, 2H), 1.35 (t, J = 8.0 Hz, 3H).
1-207				1H NMR (500 MHz, DMSO-d6) δ 12.15 (s, 1H), 9.02 (d, J = 5.5 Hz, 1H), 8.12 (dd, J = 7.5, 7.5 Hz, 2H), 7.78 (d, J = 5.5 Hz, 1H), 7.31 (dd, J = 12.0, 7.5 Hz, 2H), 4.33 (s, 3H), 2.94 (s, 3H).
1-208				1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.48 (d, J = 4.5 Hz, 1H), 7.57-7.47 (m, 3H), 7.11-7.03 (m, 2H), 4.33 (s, 3H), 2.89 (s, 6H).
1-209				1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.49 (d, J = 5.5 Hz, 1H), 8.05 (dd, J = 7.5, 7.5 Hz, 2H), 7.89 (d, J = 5.5 Hz, 1H), 7.27 (dd, J = 11.5, 7.5 Hz, 2H), 4.33 (s, 3H), 2.35 (s, 6H).
1-210	Et			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.58 (d, J = 5.5 Hz, 1H), 7.96-7.88 (m, 2H), 7.40 (d, J = 5.5 Hz, 1H), 7.35-7.27 (m, 2H), 4.33 (s, 3H), 2.70 (q, J = 8.0 Hz, 2H), 1.07 (t, J = 8.0 Hz, 3H).
1-211				1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.54 (d, J = 5.5 Hz, 1H), 8.06-7.98 (m, 2H), 7.53 (d, J = 5.5 Hz, 1H), 7.35-7.27 (m, 2H), 5.02 (s, 2H), 4.33 (s, 3H).
1-212	NO2			1H NMR (500 MHz, DMSO-d6) δ 12.15 (s, 1H), 8.78 (d, J = 5.5 Hz, 1H), 7.92 (dd, J = 7.5, 7.0 Hz, 2H), 7.79 (d, J = 5.5 Hz, 1H), 7.27 (dd, J = 11.0, 7.5 Hz, 2H), 4.33 (s, 3H).
1-213	CN			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.80 (d, J = 5.5 Hz, 1H), 7.98 (dd, J = 7.5, 7.0 Hz, 2H), 7.72 (d, J = 5.5 Hz, 1H), 7.31 (dd, J = 11.5, 7.5 Hz, 2H), 4.33 (s, 3H).
1-214				1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.96 (m, 2H), 7.66 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.68 (s, 2H), 4.33 (s, 3H), 3.28 (s, 3H).
1-215				1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.97-7.90 (m, 2H), 7.79 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.64 (q, J = 7.0 Hz, 1H), 4.33 (s, 3H), 3.23 (s, 3H), 1.36 (d, J = 7.0 Hz, 3H).
1-216				1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.97-7.90 (m, 2H), 7.79 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.36 (t, J = 8.0 Hz, 1H), 4.33 (s, 3H), 3.22 (s, 3H), 1.77-1.62 (m, 2H), 0.85 (t, J = 8.0 Hz, 3H).
1-217				1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.61 (d, J = 5.0 Hz, 1H), 7.93-7.85 (m, 2H), 7.40 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.33 (s, 3H), 3.48 (t, J = 7.5 Hz, 2H), 3.23 (s, 3H), 2.75 (t, J = 7.5 Hz, 2H).
1-218				1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.69 (d, J = 5.5 Hz, 1H), 8.0.1 (dd, J = 7.5, 7.0 Hz, 2H), 7.47 (d, J = 5.5 Hz, 1H), 7.27 (dd, J = 12.0, 7.5 Hz, 2H), 6.59 (dd, J = 16.5, 10.5 Hz, 1H), 5.55 (dd, J = 13.5, 10.5 Hz, 1H), 5.36 (dd, J = 16.5, 13.5 Hz, 1H), 4.33 (s, 3H).
1-219				1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.45 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 5.69-5.65 (m, 1H), 5.06-4.92 (m, 2H), 4.33 (s, 3H), 3.33-3.30 (m, 2H).
1-220				1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.72 (d, J = 5.5 Hz, 1H), 8.07 (dd, J = 7.5, 7.5 Hz, 2H), 7.57 (d, J = 5.5 Hz, 1H), 7.35 (dd, J = 11.5, 7.5 Hz, 2H), 4.33 (s, 3H), 4.31 (s, 1H).
1-221				1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.51 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.33 (s, 3H), 2.25 (p, J = 7.0 Hz, 1H), 0.91- 0.81 (m, 2H), 0.70-0.66 (m, 2H).
1-222				1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.56 (d, J = 5.0 Hz, 1H), 8.00-7.92 (m, 2H), 7.35-7.27 (m, 3H), 4.90 (s, 1H), 4.33 (s, 3H).
1-223				1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 9.02 (d, J = 5.5 Hz, 1H), 7.99 (dd, J = 7.5, 7.5 Hz, 2H), 7.78 (d, J = 5.5 Hz, 1H), 7.55 (dd, J = 7.5, 7.0 Hz, 2H), 7.35 (dd, J = 11.5, 7.5 Hz, 2H), 7.23 (dd, J = 11.0, 7.5 Hz, 2H), 4.33 (s, 3H).
1-224	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.15 (s, 1H), 9.17 (d, J = 5.0 Hz, 1H), 8.05 (d, J = 5.0 Hz, 1H), 6.50 (d, J = 2.5 Hz, 1H), 6.10 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H), 3.63 (s, 3H).
1-225	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 7.82 (d, J = 5.0 Hz, 1H), 7.02 (s, 1H), 6.91 (d, J = 2.0 Hz, 1H), 6.61 (d, J = 2.0 Hz, 1H), 4.37 (q, J = 9.0 Hz, 2H), 4.33 (s, 3H).
1-226	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.09 (s, 1H), 7.93 (d, J = 5.0 Hz, 1H), 7.70 (s, 1H), 4.33 (s, 3H).
1-227	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.13 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 7.86 (d, J = 2.5 Hz, 1H), 7.78 (d, J = 5.0 Hz, 1H), 7.36 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H).
1-228	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 9.19 (s, 1H), 8.92 (d, J = 5.5 Hz, 1H), 8.03 (s, 1H), 7.94 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H).
1-229	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 9.19 (s, 1H), 8.94 (d, J = 5.0 Hz, 1H), 8.12 (s, 1H), 7.96 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-230	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.93 (d, J = 5.5 Hz, 1H), 8.04 (d, J = 2.5 Hz, 1H), 7.96 (d, J = 5.5 Hz, 1H), 7.50 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H).
1-231	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.72 (s, 1H), 7.98 (s, 1H), 7.92 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-232	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.90 (d, J = 5.0 Hz, 1H), 8.09 (d, J = 2.5 Hz, 1H), 7.75 (d, J = 5.0 Hz, 1H), 7.33 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H).
1-233	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.90 (d, J = 5.5 Hz, 1H), 7.95 (d, J = 2.5 Hz, 1H), 7.39 (d, J = 5.5 Hz, 1H), 7.05 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H), 3.92 (s, 3H).
1-234	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 7.93 (d, J = 5.0 Hz, 1H), 7.73 (s, 1H), 7.67 (s, 1H), 4.33 (s, 3H), 3.79 (s, 3H).
1-235	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 7.77 (d, J = 5.0 Hz, 1H), 7.61 (s, 1H), 6.70 (t, J = 65 Hz, 1H), 4.33 (s, 3H), 3.54 (s, 3H).
1-236	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.18 (s, 1H), 7.75 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-237	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.14 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.45 (s, 1H), 7.77 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-238	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.32 (s, 1H), 7.69 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-239	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.74 (s, 1H), 7.65 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H).
1-240	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.27 (s, 1H), 7.86 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-241	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.18 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 7.96 (d, J = 5.0 Hz, 1H), 4.35-4.25 (m, 5H), 2.51 (s, 3H), 1.39 (t, J = 8.0 Hz, 3H).
1-242	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.80 (d, J = 5.0 Hz, 1H), 7.82 (s, 1H), 7.65 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-243	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.19 (s, 1H), 7.73 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H).
1-244	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 9.25 (s, 1H), 8.84 (d, J = 5.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-245	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.86 (d, J = 5.0 Hz, 1H), 8.16 (s, 1H), 7.76 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-246	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.94 (d, J = 5.0 Hz, 1H), 8.36 (s, 1H), 7.96 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 4.19 (s, 3H).
1-247	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.98 (d, J = 5.0 Hz, 1H), 7.80 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 4.16 (s, 3H), 3.67 (s, 2H).
1-248	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 7.91 (s, 1H), 7.78 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-249	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.89 (d, J = 5.5 Hz, 1H), 7.93 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H), 2.49 (s, 3H).
1-250	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.15 (s, 1H), 9.17 (d, J = 5.0 Hz, 1H), 8.05 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 1.50 (p, J = 8.0 Hz, 1H), 1.19-1.15 (m, 2H), 1.05-1.01 (m, 2H).
1-251	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.27 (s, 1H), 7.78 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-252	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.78 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 4.20 (s, 3H)
1-253	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 7.96 (s, 1H), 7.72 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-254	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 7.75 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-255	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.30 (s, 1H), 7.67 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 4.29 (s, 3H).
1-256	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 7.88 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-257	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.90 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-258	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 7.90 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-259	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 7.96 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-260	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.15 (s, 1H), 10.15 (s, 2H), 8.82 (d, J = 5.0 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-261	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 9.87 (d, J = 1.5 Hz, 1H), 9.50 (d, J = 5.0 Hz, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.29 (dd, J = 5.0, 1.5 Hz, 1H), 7.76 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-262	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.10 (s, 1H), 9.35 (dd, J = 5.0, 1.5 Hz, 1H), 8.82 (d, J = 5.0 Hz, 1H), 8.68 (dd, J = 7.5, 1.5 Hz, 1H), 7.99- 7.92 (m, 2H), 4.33 (s, 3H).
1-263	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 9.06 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.78 (d, J = 5.0 Hz, 1H), 8.00 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-264	Cl
1-265	Cl
1-266	Cl
1-267	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 7.94 (dd, J = 7.5, 1.5 Hz, 1H), 7.77 (d, J = 5.0 Hz, 1H), 7.59 (dd, J = 7.5, 1.5 Hz, 1H), 7.53 (s, 1H), 7.40 (td, J = 7.5, 1.5 Hz, 1H), 7.35 (td, J = 7.5, 1.5 Hz, 1H), 4.33 (s, 3H).
1-268	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.09 (d, J = 2.0 Hz, 1H), 7.92 (d, J = 1.5 Hz, 1H), 7.81 (dd, J = 7.5, 1.5 Hz, 1H), 7.76-7.69 (m, 2H), 7.04 (d, J = 2.0, 1H), 4.33 (s, 3H).
1-269	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 7.66 (d, J = 2.0 Hz, 1H), 7.57 (d, J = 5.0 Hz, 1H), 7.47 (d, J = 1.5 Hz, 1H), 7.17 (d, J = 1.5 Hz, 1H), 6.91 (d, J = 2.0 Hz, 1H), 4.33 (s, 3H), 3.02 (s, 6H).
1-270	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 9.32 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.60 (d, J = 1.5 Hz, 1H), 8.08 (d, J = 7.5 Hz, 1H), 7.95 (dd, J = 7.5, 1.5 Hz, 1H), 7.72 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-271	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 8.18 (dd, J = 7.5, 1.5 Hz, 1H), 8.08 (dd, J = 7.5, 1.5 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 7.58-7.54 (m, 1H), 7.50-7.46 (m, 1H), 4.33 (s, 3H).
1-272	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.15 (s, 1H), 9.46 (s, 1H), 8.99-8.95 (m, 2H), 8.73 (d, J = 5.0 Hz, 1H), 7.62 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-273	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.58 (s, 1H), 8.10 (d, J = 7.5 Hz, 1H), 7.80 (d, J = 7.5 Hz, 1H), 7.57 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 2.84 (s, 3H).
1-274	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.53 (s, 1H), 7.98 (d, J = 1.5 Hz, 1H), 7.73 (d, J = 7.5 Hz, 1H), 7.67 (dd, J = 7.5, 1.5 Hz, 1H), 7.54 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-275	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 7.98-7.89 (m, 2H), 7.87-7.84 (m, 1H), 7.64-7.59 (m, 2H), 4.33 (s, 3H).
1-276	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 7.58 (d, J = 1.5 Hz, 1H), 7.37 (d, J = 1.5 Hz, 1H), 5.32 (s, 1H), 4.50 (s, 2H), 4.33 (s, 3H), 4.02 (s, 3H), 2.34 (s, 3H).
1-277	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.32 (s, 1H), 8.17 (dd, J = 7.5, 1.5 Hz, 1H), 7.83 (dd, J = 7.5, 1.5 Hz, 1H), 7.53 (d, J = 5.0 Hz, 1H), 7.37 (t, J = 7.5 Hz, 1H), 4.33 (s, 3H), 3.79 (s, 3H).
1-278	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.28 (d, J = 1.5 Hz, 1H), 8.16 (d, J = 7.5, 1.5 Hz, 1H), 8.05 (s, 1H), 7.80 (d, J = 7.5 Hz, 1H), 7.52 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.79 (s, 3H).
1-279	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.83 (d, J = 5.0 Hz, 1H), 7.64-7.54 (m, 2H), 7.47 (d, J = 1.5 Hz, 1H), 4.33 (s, 3H), 2.51 (s, 3H).
1-280	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.39 (s, 1H), 8.07 (dd, J = 7.5, 1.5 Hz, 1H), 7.64 dd, J = 7.5, 1.5 Hz, 1H), 7.55 (d, J = 5.0 Hz, 1H), 7.45 (t, J = 7.5 Hz, 1H), 4.33 (s, 3H).
1-281	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.39 (d, J = 7.5 Hz, 1H), 7.88-7.79 (m, 2H), 7.64 (d, J = 7.5 Hz, 1H), 7.54 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-282	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 9.27 (d, J = 1.5 Hz, 1H), 8.96 (d, J = 5.0 Hz, 1H), 8.69 (d, J = 1.5 Hz, 1H), 8.15-8.05 (m, 2H), 7.87 (d, J = 5.0 Hz, 1H), 7.69 (td, J = 7.5, 1.5 Hz, 1H), 7.58 (td, J = 7.5, 1.5 Hz, 1H), 4.33 (s, 3H).
1-283	Cl			1H NMR (500 MHz, DMSO-d6) δ 13.19 (s, 1H), 12.08 (s, 1H), 9.79 (d, J = 1.5 Hz, 1H), 9.21 (d, J = 1.5 Hz, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.44 (dd, J = 7.5, 1.5 Hz, 1H), 8.33 (dd, J = 7.5, 1.5 Hz, 1H), 8.12 (t, J = 7.5 Hz, 1H), 7.85 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-284	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.15 (s, 1H), 9.73 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.49-8.41 (m, 2H), 8.35 (dd, J = 7.5, 1.5 Hz, 1H), 7.93 (d, J = 7.5 Hz, 1H), 7.74 (t, J = 7.5 Hz, 1H), 7.63 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-285	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.10 (s, 1H), 9.69 (s, 1H), 9.04 (d, J = 5.0 Hz, 1H), 8.43 (d, J = 1.5 Hz, 1H), 8.07-7.97 (m, 3H), 4.33 (s, 3H), 3.85 (s, 1H).
1-286	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 9.13 (d, J = 5.5 Hz, 1H), 8.91-8.83 (m, 2H), 8.23 (dd, J = 7.5, 1.5 Hz, 2H), 7.93 (t, J = 7.5 Hz, 1H), 7.65 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H).
1-287	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.91-8.86 (m, 3H), 8.74 (d, J = 1.5 Hz, 1H), 8.29-8.21 (m, 2H), 7.62 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-288	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.28 (dd, J = 7.5, 1.5 Hz, 1H), 7.93 (d, J = 7.5 Hz, 1H), 7.80 (d, J = 1.5 Hz, 1H), 7.53 (d, J = 5.0 Hz, 1H), 7.05 (s, 1H), 4.33 (s, 3H), 3.62 (s, 3H), 3.55 (s, 2H), 2.18 (s, 3H).
1-289	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.77 (d, J = 1.5 Hz, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.24 (dd, J = 7.5, 1.5 Hz, 1H), 7.74-7.68 (m, 2H), 7.17 (d, J = 7.5 Hz, 1H), 6.63 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H), 3.79 (s, 3H).
1-290	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.00-7.92 (m, 2H), 7.73 (dd, J = 7.5, 1.5 Hz, 1H), 7.47 (td, J = 7.5, 1.5 Hz, 1H), 7.31 (td, J = 7.5, 1.5 Hz, 1H), 7.14 (s, 1H), 4.33 (s, 3H), 3.82 (s, 3H).
1-291	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 7.97 (d, J = 7.5 Hz, 1H), 7.95-7.88 (m, 3H), 7.39 (dd, J = 7.5, 1.5 Hz, 1H), 4.33 (s, 3H).
1-292	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.04 (dd, J = 7.5, 1.5 Hz, 1H), 7.91 (dd, J = 7.5, 1.5 Hz, 1H), 7.76 (d, J = 5.0 Hz, 1H), 7.65 (d, J = 2.5 Hz, 1H), 7.56 (t, J = 7.5 Hz, 1H), 7.44 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H).
1-293	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 8.07-7.97 (m, 2H), 7.75 (d, J = 5.0 Hz, 1H), 7.66-7.56 (m, 2H), 7.50 (t, J = 7.5 Hz, 1H), 4.33 (s, 3H).
1-294	Cl
1-295	Cl
1-296	Cl
1-297	Cl
1-298	Cl
1-299	Cl
1-300	Cl
1-301	Cl
1-302	Cl
1-303	Cl
1-304	Cl
1-305	Cl
1-306	Cl
1-307	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 7.65-7.57 (m, 2H), 7.25 (d, J = 5.0 Hz, 1H), 7.11-7.03 (m, 2H), 4.40-4.32 (m, 2H), 1.50 (t, J = 8.0 Hz, 3H).
1-308	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.05-7.97 (m, 2H), 7.53 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.25 (t, J = 5.0 Hz, 2H), 1.74-1.70 (m, 2H), 0.89 (t, J = 8.0 Hz, 3H).
1-309	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.56 (s, 1H), 12.06 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.05- 7.97 (m, 2H), 7.52 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H).
1-310	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.49 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 6.07-6.04 (m, 1H), 5.41-5.32 (m, 1H), 5.27- 5.16 (m, 1H), 4.43-4.37 (m, 2H).
1-311	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.04-7.96 (m, 2H), 7.51 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 5.57 (s, 2H), 3.35 (s, 3H).
1-312	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.53 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.10 (t, J = 8.0 Hz, 2H), 2.92 (t, J = 8.0 Hz, 2H), 2.09 (s, 3H).
1-313	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.50 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 5.05 (s, 2H), 3.78 (s, 3H).
1-314	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.07-7.99 (m, 2H), 7.66 (d, J = 5.0 Hz, 1H), 7.59-7.53 (m, 4H), 7.52-7.49 (m, 1H), 7.35-7.27 (m, 2H).
1-315	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.06-7.99 (m, 2H), 7.69-7.60 (m, 3H), 7.57-7.54 (m, 2H), 7.35-7.27 (m, 2H).
1-316	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.86 (d, J = 5.0 Hz, 1H), 8.05-7.98 (m, 2H), 7.59 (d, J = 5.0 Hz, 1H), 7.41 (dd, J = 7.5, 1.5 Hz, 2H), 7.35-7.27 (m, 2H), 7.08-7.02 (m, 2H), 5.45 (s, 2H).
1-317	Cl	CH3
1-318	Cl
1-319	Cl
1-320	Cl
1-321	Cl
1-322	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.24 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.32 (s, 1H), 7.64 (d, J = 5.0 Hz, 1H), 6.14-6.07 (m, 1H), 3.91 (s, 3H), 3.36-3.30 (m, 2H), 3.05 (t, J = 7.0, Hz, 2H), 2.60 (t, J = 7.0 Hz, 2H), 2.20 (s, 3H).
1-323	Cl
1-324	Cl
1-325	Cl
1-326	Cl
1-327	Cl
1-328	Cl
1-329	Cl
1-330	Cl
1-331	Cl
1-332	Cl
1-333	Cl
1-334	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 8.23 (s, 1H), 7.64- 7.57 (m, 2H), 7.25 (d, J = 5.0 Hz, 1H), 7.11- 7.03 (m, 2H), 3.95 (s, 3H).
1-335	Cl
1-336	Cl
1-337	Cl
1-338	Cl
1-339	Cl
1-340	Cl
1-341	Cl
1-342	Cl
1-343	Cl
1-344	Cl
1-345	Cl
1-346	Cl
1-347	Cl
1-348	Cl
1-349	Cl
1-350	Cl
1-351	Cl
1-352	Cl
1-353	Cl
1-354	Cl
1-355	Cl
1-356	Cl
1-357	Cl
1-358	Cl
1-359	Cl
1-360	Cl
1-361	Cl
1-362	Cl
1-363	Cl
1-364	Cl
1-365	Cl
1-366	Cl
1-367	Cl
1-368	Cl
1-369	Cl
1-370	Cl
1-371	Cl
1-372	Cl
1-373	Cl
1-374	Cl
1-375	Cl
1-376	Cl
1-377	Cl
1-378	Cl
1-379	Cl
1-380	Cl
1-381	Cl
1-382	Cl
1-383	Cl
1-384	Cl
1-385	Cl
1-386	Cl
1-387	Cl
1-388	Cl
1-389	Cl
1-390	Cl
1-391	Cl
1-392	Cl
1-393	Cl
1-394	Cl
1-395	Cl
1-396	Cl
1-397	Cl
1-398	Cl
1-399	Cl
1-400	Cl
1-401	Cl
1-402	Cl
1-403	Cl
1-404	Cl
1-405	Cl
1-406	Cl
1-407	Cl
1-408	Cl
1-409	Cl
1-410	Cl
1-411	Cl
1-412	Cl
1-413	Cl
1-414	Cl
1-415	Cl
1-416	Cl
1-417	Cl
1-418	Cl
1-419	Cl
1-420	Cl
1-421	Cl
1-422	Cl
1-423	Cl
1-424	Cl
1-425	Cl
1-426	Cl
1-427	Cl
1-428	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.10 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.38-8.35 (m, 2H), 8.18- 8.07 (m, 2H), 8.03-8.00 (m, 1H), 7.90 (t, J = 8.5 Hz, 1H), 7.65 (d, J = 5.0 Hz, 1H), 7.59-7.56 (m, 1H), 7.52-7.50 (m, 1H), 4.31 (s, 3H).
1-429	Cl
1-430	Cl
1-431	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.22 (s, 1H), 9.29 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.59 (d, J = 5.0 Hz, 1H), 8.33 (s, 1H), 8.26-8.22 (m, 2H), 8.17-8.14 (m, 2H), 7.66 (d, J = 5.0 Hz, 1H), 3.92 (s, 3H).
1-432	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.93-8.85 (m, 2H), 8.81-8.74 (m, 1H), 8.43- 8.36 (m, 2H), 8.02-7.99 (m, 2H), 7.74-7.60 (m, 5H), 3.92 (s, 3H).
1-433	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.51 (s, 1H), 8.20 (dd, J = 7.5, 2.0 Hz, 1H), 8.07-8.03 (m, 2H), 7.67 (d, J = 5.0 Hz, 1H), 7.65-7.58 (m, 2H), 7.44-7.41 (m, 1H), 7.35-7.32 (m, 1H), 3.96 (s, 3H).
1-434	Cl
1-435	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.90 (d, J = 5.0 Hz, 1H), 8.55 (d, J = 2.0 Hz, 1H), 8.48 (dd, J = 7.5, 2.0 Hz, 1H), 8.39 (d, J = 7.5 Hz, 1H), 8.32 (s, 1H), 8.11-8.05 (m, 2H), 7.62 (d, J = 5.0 Hz, 1H), 7.56 (td, J = 7.5, 2.0 Hz, 1H), 7.48 (td, J = 7.5, 2.0 Hz, 1H), 3.92 (s, 3H).
1-436	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.13 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.58-8.48 (m, 2H), 8.29 (s, 1H), 7.74 (td, J = 7.5, 2.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 7.24-7.22 (m, 1H), 3.91 (s, 3H).
1-437	Cl
1-438	Cl
1-439	Cl
1-440	Cl
1-441	Cl
1-442	Cl
1-443	Cl
1-444	Cl
1-445	Cl
1-446	Cl
1-447	Cl
1-448	Cl
1-449	Cl
1-450	Cl
1-451	Cl
1-452	Cl
1-453	Cl
1-454	Cl
1-455	Cl
1-456	Cl
1-457	Cl
1-458	Cl
1-459	Cl
1-460	Cl
1-461	Cl
1-462	Cl
1-463	Cl
1-464	Cl
1-465	Cl
1-466	Cl
1-467	Cl
1-468	Cl
1-469	Cl
1-470	Cl
1-471	Cl
1-472	Cl
1-473	Cl
1-474	Cl
1-475	Cl
1-476	Cl
1-477	Cl
1-478	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 9.25 (s, 2H), 8.83 (d, J = 5.0 Hz, 1H), 8.31 (s, 1H), 7.75 (d, J = 5.0 Hz, 1H), 3.91 (s, 3H), 3.85 (s, 3H).
1-479	Cl
1-480	Cl
1-481	Cl
1-482	Cl
1-483	Cl
1-484	Cl
1-485	Cl
1-486	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.10 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.32 (s, 1H), 7.78 (d, J = 5.0 Hz, 1H), 6.87 (s, 1H), 3.93 (s, 3H), 3.92 (s, 3H), 2.41 (s, 3H).
1-487	Cl
1-488	Cl
1-489	Cl
1-490	Cl
1-491	Cl
1-492	Cl
1-493	Cl
1-494	Cl
1-495	Cl
1-496	Cl
1-497	Cl
1-498	Cl
1-499	Cl
1-500	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.37 (s, 1H), 7.92 (d, J = 5.0 Hz, 1H), 7.67 (s, 1H), 7.49 (d, J = 2.0 Hz, 1H), 6.69 (d, J = 2.0 Hz, 1H), 3.92 (s, 3H).
1-501	Cl
1-502	Cl
1-503	Cl
1-504	Cl
1-505	Cl
1-506	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 8.37 (s, 1H), 7.94 (d, J = 5.0 Hz, 1H), 7.52 (d, J = 2.0 Hz, 1H), 7.13 (d, J = 2.0 Hz, 1H), 3.92 (s, 3H).
1-507	Cl
1-508	Cl
1-509	Cl
1-510	Cl
1-511	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.58 (d, J = 5.0 Hz, 1H), 8.36 (s, 1H), 7.98-7.90 (m, 2H), 7.50 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.33 (s, 3H), 2.52 (s, 3H).
1-512	F
1-513	Br
1-514
1-515	CF3			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 8.36 (s, 1H), 8.02- 7.95 (m, 2H), 7.58 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.01 (s, 3H).
1-516				1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.34 (s, 1H), 8.00- 7.93 (m, 2H), 7.69-7.60 (m, 3H), 7.47-7.35 (m, 3H), 7.35-7.27 (m, 2H), 3.83 (s, 3H).
1-517				1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.57 (d, J = 5.0 Hz, 1H), 8.32 (s, 1H), 8.09- 8.01 (m, 2H), 7.50 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.03 (s, 3H), 3.67 (s, 3H).
1-518
1-519
1-520
1-521				1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.57 (d, J = 5.0 Hz, 1H), 8.33 (s, 1H), 8.04- 7.97 (m, 2H), 7.47 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.02 (s, 3H), 3.00 (q, J = 8.0 Hz, 2H), 1.19 (t, J = 8.0 Hz, 3H).
1-522
1-523				1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.31 (s, 1H), 8.04- 7.97 (m, 2H), 7.55 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.03 (s, 3H), 2.63-2.61 (m, 1H), 2.58-5.56 (m, 1H), 1.20 (t, J = 8.0 Hz, 3H).
1-524
1-525				1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.38 (d, J = 5.0 Hz, 1H), 8.33 (s, 1H), 8.06- 7.98 (m, 2H), 7.46 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 3.98 (s, 3H), 2.80 (s, 6H).
1-526
1-527	Et
1-528
1-529	NO2			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.96 (d, J = 5.0 Hz, 1H), 8.35 (s, 1H), 7.98- 7.91 (m, 2H), 7.72 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.26 (s, 3H).
1-530	CN			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 9.01 (d, J = 5.0 Hz, 1H), 8.33 (s, 1H), 8.05- 7.97 (m, 2H), 7.70 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 3.92 (s, 3H).
1-531				1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.37 (s, 1H), 8.03- 7.95 (m, 2H), 7.65 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.68 (s, 2H), 4.33 (s, 3H), 3.28 (s, 3H).
1-532
1-533
1-534
1-535				1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.61 (d, J = 5.0 Hz, 1H), 8.03-7.96 (m, 2H), 7.35-7.25 (m, 3H), 6.53 (dd, J = 16.5, 10.0 Hz, 1H), 5.60-5.67 (m, 1H), 5.31 5.29 (m, 1H), 4.33 (s, 3H).
1-536
1-537				1H NMR (500 MHz, DMSO-d6) δ 12.15 (s, 1H), 9.01 (d, J = 5.0 Hz, 1H), 8.33 (s, 1H), 8.05- 7.97 (m, 2H), 7.70 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.03 (s, 3H), 3.92 (s, 1H).
1-538
1-539
1-540
1-541	Cl
1-542	Cl
1-543	Cl
1-544	Cl
1-545	Cl
1-546	Cl
1-547	Cl
1-548	Cl
1-549	Cl
1-550	Cl
1-551	Cl
1-552	Cl
1-553	Cl
1-554	Cl
1-555	Cl
1-556	Cl
1-557	Cl
1-558	Cl
1-559	Cl
1-560	Cl
1-561	Cl
1-562	Cl
1-563	Cl
1-564	Cl
1-565	Cl
1-566	Cl
1-567	Cl
1-568	Cl
1-569	Cl
1-570	Cl
1-571	Cl
1-572	Cl
1-573	Cl
1-574	Cl
1-575	Cl
1-576	Cl
1-577	Cl
1-578	Cl
1-579	Cl
1-580	Cl
1-581	Cl
1-582	Cl
1-583	Cl
1-584	Cl
1-585	Cl
1-586	Cl
1-587	Cl
1-588	Cl
1-589	Cl
1-590	Cl
1-591	Cl
1-592	Cl
1-593	Cl
1-594	Cl
1-595	Cl
1-596	Cl
1-597	Cl
1-598	Cl
1-599	Cl
1-600	Cl
1-601	Cl
1-602	Cl
1-603	Cl
1-604	Cl
1-605	Cl
1-606	Cl
1-607	Cl
1-608	Cl
1-609	Cl
1-610	Cl
1-611	Cl
1-612	Cl
1-613	Cl
1-614	Cl
1-615	Cl
1-616	Cl
1-617	Cl
1-618	Cl
1-619	Cl
1-620	Cl
1-621	Cl
1-622	Cl
1-623	Cl
1-624	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.16 (s, 1H), 10.08 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04- 7.96 (m, 2H), 7.51 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 2.45 (s, 3H).
1-625	Cl
1-626	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.34-8.26 (m, 2H), 7.55 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.61 (s, 3H), 2.18 (p, J = 7.0 Hz, 1H), 1.13 (m, 2H), 0.88 (m, 2H).
1-627	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.34-8.26 (m, 2H), 7.55 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.46 (hept, J = 8.0 Hz, 1H), 1.65 (d, J = 8.0 Hz, 6H).
1-628	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.03-7.96 (m, 2H), 7.67 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.32 (s, 2H), 3.94 (s, 3H), 2.99 (s, 3H).
1-629	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 8.08-8.00 (m, 2H), 7.46 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.93 (s, 3H), 3.59 (s, 3H), 3.51 (s, 2H).
1-630	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 8.11-8.02 (m, 4H), 7.65 (d, J = 5.0 Hz, 1H), 7.54-7.46 (m, 1H), 7.48-7.40 (m, 2H), 7.35-7.27 (m, 2H), 3.97 (s, 3H).
1-631	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.96 (m, 2H), 7.89 (s, 1H), 7.65 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.40 (q, J = 8.0 Hz, 2H), 1.49 (t, J = 8.0 Hz, 3H).
1-632	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.13 (s, 1H), 10.06 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.70 (dd, J = 5.0, 2.0 Hz, 1H), 8.46-8.44 (m, 2H), 8.11- 8.03 (m, 2H), 7.64 (d, J = 5.0 Hz, 1H), 7.57 (dd, J = 8.0, 2.0 Hz, 1H), 7.35-7.27 (m, 2H), .
1-633	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.08-8.00 (m, 2H), 7.63 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.94 (s, 3H), 3.63 (t, J = 8.0 Hz, 4H), 3.36 (t, J = 8.0 Hz, 4H).
1-634	Cl	CH3
1-635	Cl
1-636	Cl
1-637	Cl
1-638	Cl
1-639	Cl
1-640	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 7.84 (d, J = 5.0 Hz, 1H), 6.26-6.19 (m, 1H), 4.23-4.17 (m, 2H), 3.86 (s, 3H), 3.79 (t, J = 5.0 Hz, 2H), 2.50 (s, 3H), 2.40 (t, J = 5.0, 2H).
1-641	Cl
1-642	Cl
1-643	Cl
1-644	Cl
1-645	Cl
1-646	Cl
1-647	Cl
1-648	Cl
1-649	Cl
1-650	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.05-7.97 (m, 2H), 7.53 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.88 (s, 3H), 2.50 (s, 3H).
1-651	Cl
1-652	Cl
1-653	Cl
1-654	Cl
1-655	Cl
1-656	Cl
1-657	Cl
1-658	Cl
1-659	Cl
1-660	Cl
1-661	Cl
1-662	Cl
1-663	Cl
1-664	Cl
1-665	Cl
1-666	Cl
1-667	Cl
1-668	Cl
1-669	Cl
1-670	Cl
1-671	Cl
1-672	Cl
1-673	Cl
1-674	Cl
1-675	Cl
1-676	Cl
1-677	Cl
1-678	Cl
1-679	Cl
1-680	Cl
1-681	Cl
1-682	Cl
1-683	Cl
1-684	Cl
1-685	Cl
1-686	Cl
1-687	Cl
1-688	Cl
1-689	Cl
1-690	Cl
1-691	Cl
1-692	Cl
1-693	Cl
1-694	Cl
1-695	Cl
1-696	Cl
1-697	Cl
1-698	Cl
1-699	Cl
1-700	Cl
1-701	Cl
1-702	Cl
1-703	Cl
1-704	Cl
1-705	Cl
1-706	Cl
1-707	Cl
1-708	Cl
1-709	Cl
1-710	Cl
1-711	Cl
1-712	Cl
1-713	Cl
1-714	Cl
1-715	Cl
1-716	Cl
1-717	Cl
1-718	Cl
1-719	Cl
1-720	Cl
1-721	Cl
1-722	Cl
1-723	Cl
1-724	Cl
1-725	Cl
1-726	Cl
1-727	Cl
1-728	Cl
1-729	Cl
1-730	Cl
1-731	Cl
1-732	Cl
1-733	Cl
1-734	Cl
1-735	Cl
1-736	Cl
1-737	Cl
1-738	Cl
1-739	Cl
1-740	Cl
1-741	Cl
1-742	Cl
1-743	Cl
1-744	Cl
1-745	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.98 (d, J = 5.0 Hz, 1H), 8.35 (dd, J = 7.5, 2.0 Hz, 1H), 8.13-8.10 (m, 2H), 8.04 (dt, J = 7.5, 2.0 Hz, 1H), 7.94-7.85 (m, 2H), 7.59 (td, J = 7.5, 2.0 Hz, 1H), 7.52 (td, J = 7.5, 2.00 Hz, 1H), 3.88 (s, 3H), 2.51 (s, 3H).
1-746	Cl
1-747	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 9.28 (s, 1H), 8.93 (d, J = 5.0 Hz, 1H), 8.60 (d, J = 5.5 Hz, 1H), 8.20-8.17 (m, 2H), 7.89-7.78 (m, 3H), 3.87 (s, 3H), 2.51 (s, 3H).
1-748	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.93-8.86 (m, 2H), 8.78 (dd, J = 8.0, 2.5 Hz, 1H), 8.38 (s, 1H), 8.05-7.94 (m, 2H), 7.83 (d, J = 5.0 Hz, 1H), 7.74-7.60 (m, 4H), 3.88 (s, 3H), 2.51 (s, 3H).
1-749	Cl
1-750	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.97 (d, J = 5.0 Hz, 1H), 8.21 (dd, J = 7.5, 2.0 Hz, 1H), 8.05-8.03 (m, 2H), 7.85 (d, J = 5.0 Hz, 1H), 7.66-7.58 (m, 2H), 7.44 (td, J = 7.5, 2.0 Hz, 1H), 7.35 (td, J = 7.5, 2.0 Hz, 1H), 3.88 (s, 3H), 2.52 (s, 3H).
1-751	Cl
1-752	Cl
1-753	Cl
1-754	Cl
1-755	Cl
1-756	Cl
1-757	Cl
1-758	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.91 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.45 (d, J = 5.0 Hz, 1H), 7.87 (d, J = 5.0 Hz, 1H), 7.43 (d, J = 5.0 Hz, 1H), 3.87 (s, 3H), 2.50 (s, 3H), 2.48 (s, 3H).
1-759	Cl
1-760	Cl
1-761	Cl
1-762	Cl
1-763	Cl
1-764	Cl
1-765	Cl
1-766	Cl
1-767	Cl
1-768	Cl
1-769	Cl
1-770	Cl
1-771	Cl
1-772	Cl
1-773	Cl
1-774	Cl
1-775	Cl
1-776	Cl
1-777	Cl
1-778	Cl
1-779	Cl
1-780	Cl
1-781	Cl
1-782	Cl
1-783	Cl
1-784	Cl
1-785	Cl
1-786	Cl
1-787	Cl
1-788	Cl
1-789	Cl
1-790	Cl
1-791	Cl
1-792	Cl
1-793	Cl
1-794	Cl
1-795	Cl
1-796	Cl
1-797	Cl
1-798	Cl
1-799	Cl
1-800	Cl
1-801	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.96 (d, J = 5.0 Hz, 1H), 7.94 (d, J = 5.0 Hz, 1H), 7.80 (s, 1H), 6.97 (s, 1H), 3.92 (s, 3H), 3.87 (s, 3H), 2.51 (s, 3H).
1-802	Cl
1-803	Cl
1-804	Cl
1-805	Cl
1-806	Cl
1-807	Cl
1-808	Cl
1-809	Cl
1-810	Cl
1-811	Cl
1-812	Cl
1-813	Cl
1-814	Cl
1-815	Cl
1-816	Cl
1-817	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.07 (d, J = 2.0 Hz, 1H), 7.94 (d, J = 5.0 Hz, 1H), 7.26 (d, J = 2.0 Hz, 1H), 6.98 (t, J = 2.0 Hz, 1H), 3.86 (s, 3H), 2.51 (s, 3H).
1-818	Cl
1-819	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.23 (s, 1H), 8.98 (d, J = 5.0 Hz, 1H), 7.98 (d, J = 5.0 Hz, 1H), 7.58 (d, J = 2.0 Hz, 1H), 7.47 (d, J = 2.0 Hz, 1H), 7.15 (t, J = 2.0 Hz, 1H), 3.86 (s, 3H), 2.51 (s, 3H).
1-820	Cl
1-821	Cl
1-822	Cl
1-823	Cl
1-824	Cl
1-825	Cl
1-826	Cl
1-827	CH3
1-828	F
1-829	Br
1-830				1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.57 (d, J = 5.0 Hz, 1H), 7.95-7.87 (m, 2H), 7.37 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.87 (s, 3H), 2.85 (hept, J = 7.0 Hz, 1H), 2.50 (s, 3H), 1.11 (d, J = 7.0 Hz, 6H).
1-831	CF3			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 8.05-7.97 (m, 2H), 7.58 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.89 (s, 3H), 2.51 (s, 3H).
1-832
1-833
1-834				1H NMR (500 MHz, DMSO-d6) δ 12.33 (s, 1H), 8.59 (d, J = 5.0 Hz, 1H), 8.10-8.02 (m, 2H), 7.94 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.10 (q, J = 8.0 Hz, 2H), 3.88 (s, 3H), 2.51 (s, 3H), 1.34 (t, J = 8.0 Hz, 3H).
1-835
1-836
1-837				1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.56 (d, J = 5.0 Hz, 1H), 8.05-7.98 (m, 2H), 7.47 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.88 (s, 3H), 3.00 (q, J = 8.0 Hz, 2H), 2.50 (s, 3H), 1.19 (t, J = 8.0 Hz, 3H).
1-838
1-839				1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.05-7.97 (m, 2H), 7.56 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.87 (s, 3H), 2.61-2.59 (m, 1H), 2.57-2.55 (m, 1H) 2.50 (s, 3H), 1.20 (t, J = 8.0 Hz, 3H).
1-840
1-841				1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.38 (d, J = 5.0 Hz, 1H), 8.07-8.00 (m, 2H), 7.46 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.87 (s, 3H), 2.76 (s, 6H), 2.49 (s, 3H).
1-842
1-843	Et
1-844
1-845	NO2			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.96 (d, J = 5.0 Hz, 1H), 7.99-7.91 (m, 2H), 7.71 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.89 (s, 3H), 2.52 (s, 3H).
1-846	CN			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 9.02 (d, J = 5.0 Hz, 1H), 8.06-7.98 (m, 2H), 7.73 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.89 (s, 3H), 2.51 (s, 3H).
1-847				1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.55 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.68 (s, 2H), 3.88 (s, 3H), 3.28 (s, 3H), 2.51 (s, 3H).
1-848
1-849
1-850
1-851
1-852
1-853
1-854
1-855
1-856				1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.62 (d, J = 5.0 Hz, 1H), 7.60-7.52 (m, 2H), 7.35-7.27 (m, 2H), 7.23-7.15 (m, 2H), 3.79 (s, 3H), 2.49 (s, 3H).
1-857	Cl
1-858	Cl
1-859	Cl
1-860	Cl
1-861	Cl
1-862	Cl
1-863	Cl
1-864	Cl
1-865	Cl
1-866	Cl
1-867	Cl
1-868	Cl
1-869	Cl
1-870	Cl
1-871	Cl
1-872	Cl
1-873	Cl
1-874	Cl
1-875	Cl
1-876	Cl
1-877	Cl
1-878	Cl
1-879	Cl
1-880	Cl
1-881	Cl
1-882	Cl
1-883	Cl
1-884	Cl
1-885	Cl
1-886	Cl
1-887	Cl
1-888	Cl
1-889	Cl
1-890	Cl
1-891	Cl
1-892	Cl
1-893	Cl
1-894	Cl
1-895	Cl
1-896	Cl
1-897	Cl
1-898	Cl
1-899	Cl
1-900	Cl
1-901	Cl
1-902	Cl
1-903	Cl
1-904	Cl
1-905	Cl
1-906	Cl
1-907	Cl
1-908	Cl
1-909	Cl
1-910	Cl
1-911	Cl
1-912	Cl
1-913	Cl
1-914	Cl
1-915	Cl
1-916	Cl
1-917	Cl
1-918	Cl
1-919	Cl
1-920	Cl
1-921	Cl
1-922	Cl
1-923	Cl
1-924	Cl
1-925	Cl
1-926	Cl
1-927	Cl
1-928	Cl
1-929	Cl
1-930	Cl
1-931	Cl
1-932	Cl
1-933	Cl
1-934	Cl
1-935	Cl
1-936	Cl
1-937	Cl
1-938	Cl
1-939	Cl
1-940	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 9.15 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.03- 7.95 (m, 2H), 7.70 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 3.82 (s, 3H).
1-941	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 8.02-7.95 (m, 2H), 7.74 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.07 (q, J = 8.0 Hz, 2H), 1.29 (t, J = 8.0 Hz, 3H).
1-942	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.73 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.01 (s, 3H), 3.88 (s, 3H).
1-943	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.68 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.18 (t, J = 8.0 Hz, 2H), 3.96 (t, J = 8.0 Hz, 2H), 3.58 (s, 3H), 2.47 (s, 3H).
1-944	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.10 (s, 1H), 10.40 (s, 1H), 8.94 (d, J = 5.0 Hz, 1H), 8.05- 7.97 (m, 2H), 7.62 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 3.36 (t, J = 5.5 Hz, 4H), 1.62- 1.56 (m, 2H), 1.51 (p, J = 7.0 Hz, 4H).
1-945	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.94 (d, J = 5.0 Hz, 1H), 8.05-7.93 (m, 4H), 7.83 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 7.14-7.08 (m, 2H), 3.86 (s, 3H), 3.79 (s, 3H).
1-946	Cl	CH3		1H NMR (500 MHz, DMSO-d6) δ 12.94 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 2.59 (s, 3H), 2.46 (s, 3H).
1-947	Cl
1-948	Cl
1-949	Cl
1-950	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.66 (d, J = 5.0 Hz, 1H), 6.18 (t, J = 6.0 Hz, 1H), 2.44 (s, 3H), 2.13-1.92 (m, 4H), 1.76-1.58 (m, 2H), 1.48-1.35 (m, 2H).
1-951	Cl
1-952	Cl
1-953	Cl
1-954	Cl
1-955	Cl
1-956	Cl
1-957	Cl
1-958	Cl
1-959	Cl
1-960	Cl
1-961	Cl
1-962	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 7.63-7.55 (m, 2H), 7.12-7.03 (m, 3H), 2.38 (s, 3H).
1-963	Cl
1-964	Cl
1-965	Cl
1-966	Cl
1-967	Cl
1-968	Cl
1-969	Cl
1-970	Cl
1-971	Cl
1-972	Cl
1-973	Cl
1-974	Cl
1-975	Cl
1-976	Cl
1-977	Cl
1-978	Cl
1-979	Cl
1-980	Cl
1-981	Cl
1-982	Cl
1-983	Cl
1-984	Cl
1-985	Cl
1-986	Cl
1-987	Cl
1-988	Cl
1-989	Cl
1-990	Cl
1-991	Cl
1-992	Cl
1-993	Cl
1-994	Cl
1-995	Cl
1-996	Cl
1-997	Cl
1-998	Cl
1-999	Cl
1-1000	Cl
1-1001	Cl
1-1002	Cl
1-1003	Cl
1-1004	Cl
1-1005	Cl
1-1006	Cl
1-1007	Cl
1-1008	Cl
1-1009	Cl
1-1010	Cl
1-1011	Cl
1-1012	Cl
1-1013	Cl
1-1014	Cl
1-1015	Cl
1-1016	Cl
1-1017	Cl
1-1018	Cl
1-1019	Cl
1-1020	Cl
1-1021	Cl
1-1022	Cl
1-1023	Cl
1-1024	Cl
1-1025	Cl
1-1026	Cl
1-1027	Cl
1-1028	Cl
1-1029	Cl
1-1030	Cl
1-1031	Cl
1-1032	Cl
1-1033	Cl
1-1034	Cl
1-1035	Cl
1-1036	Cl
1-1037	Cl
1-1038	Cl
1-1039	Cl
1-1040	Cl
1-1041	Cl
1-1042	Cl
1-1043	Cl
1-1044	Cl
1-1045	Cl
1-1046	Cl
1-1047	Cl
1-1048	Cl
1-1049	Cl
1-1050	Cl
1-1051	Cl
1-1052	Cl
1-1053	Cl
1-1054	Cl
1-1055	Cl
1-1056	Cl
1-1057	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.86 (d, J = 5.0 Hz, 1H), 8.52 (d, J = 1.5 Hz, 1H), 8.17 (dd, J = 7.5, 1.5 Hz, 1H), 8.09-7.99 (m, 3H), 7.67-7.58 (m, 2H), 7.56 (d, J = 5.0 Hz, 1H), 2.44 (s, 3H).
1-1058	Cl
1-1059	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 9.26 (s, 1H), 8.84 (d, J = 5.0 Hz, 1H), 8.59 (d, J = 5.5 Hz, 1H), 8.22-8.13 (m, 2H), 7.86-7.79 (m, 2H), 7.60 (d, J = 5.0 Hz, 1H), 2.46 (s, 3H).
1-1060	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.90 (dd, J = 7.5, 1.5 Hz, 1H), 8.84 (d, J = 5.0 Hz, 1H), 8.81-8.73 (m, 1H), 8.38 (d, J = 1.5 Hz, 1H), 8.09-7.97 (m, 2H), 7.74-7.59 (m, 5H), 2.48 (s, 3H).
1-1061	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.20 (dd, J = 7.5, 1.5 Hz, 1H), 8.15-8.01 (m, 2H), 7.69 (d, J = 5.0 Hz, 1H), 7.64-7.57 (m, 2H), 7.48-7.41 (m, 1H), 7.39-7.26 (m, 1H), 2.45 (s, 3H).
1-1062	Cl
1-1063	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.13 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.52 (d, J = 1.5 Hz, 1H), 8.47 (dd, J = 7.5, 1.5 Hz, 1H), 8.38 (d, J = 7.5 Hz, 1H), 8.16-8.02 (m, 2H), 7.60-7.52 (m, 2H), 7.53-7.42 m, 1H), 2.44 (s, 3H).
1-1064	Cl
1-1065	Cl
1-1066	Cl
1-1067	Cl
1-1068	Cl
1-1069	Cl
1-1070	Cl
1-1071	Cl
1-1072	Cl
1-1073	Cl
1-1074	Cl
1-1075	Cl
1-1076	Cl
1-1077	Cl
1-1078	Cl
1-1079	Cl
1-1080	Cl
1-1081	Cl
1-1082	Cl
1-1083	Cl
1-1084	Cl
1-1085	Cl
1-1086	Cl
1-1087	Cl
1-1088	Cl
1-1089	Cl
1-1090	Cl
1-1091	Cl
1-1092	Cl
1-1093	Cl
1-1094	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.13 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 8.31 (dd, J = 5.5, 5.0 Hz, 1H), 8.16-8.01 (m, 1H), 7.88-7.85 (m, 1H), 7.73 (d, J = 5.0 Hz, 1H), 2.44 (s, 3H).
1-1095	Cl
1-1096	Cl
1-1097	Cl
1-1098	Cl
1-1099	Cl
1-1100	Cl
1-1101	Cl
1-1102	Cl
1-1103	Cl
1-1104	Cl
1-1105	Cl
1-1106	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 9.48 (s, 2H), 8.80 (d, J = 5.0 Hz, 1H), 7.69 (d, J = 5.0 Hz, 1H), 3.85 (s, 3H), 2.44 (s, 3H).
1-1107	Cl
1-1108	Cl
1-1109	Cl
1-1110	Cl
1-1111	Cl
1-1112	Cl
1-1113	Cl
1-1114	Cl
1-1115	Cl
1-1116	Cl
1-1117	Cl
1-1118	Cl
1-1119	Cl
1-1120	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 7.84 (t, J = 65.0 Hz, 1H), 7.65 (d, J = 5.0 Hz, 1H), 6.98 (s, 1H), 2.45 (s, 3H), 2.39 (s, 3H).
1-1121	Cl
1-1122	Cl
1-1123	Cl
1-1124	Cl
1-1125	Cl
1-1126	Cl
1-1127	Cl
1-1128	Cl
1-1129	Cl
1-1130	Cl
1-1131	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 9.17 (d, J = 5.0 Hz, 1H), 8.05 (d, J = 5.0 Hz, 1H), 7.49-7.32 (m, 1H), 6.38-6.27 (m, 1H), 2.63 (s, 3H).
1-1132	Cl
1-1133	Cl
1-1134	Cl
1-1135	Cl
1-1136	Cl
1-1137	Cl
1-1138	Cl
1-1139	Cl
1-1140	Cl
1-1141	CH3
1-1142	F
1-1143	Br
1-1144
1-1145	CF3			1H NMR (500 MHz, DMSO-d6) δ 12.13 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 8.00-7.93 (m, 2H), 7.48 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.45 (s, 3H).
1-1146
1-1147				1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.53 (d, J = 5.0 Hz, 1H), 8.06-7.98 (m, 2H), 7.46 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.64 (s, 3H), 2.45 (s, 3H).
1-1148
1-1149
1-1150				1H NMR (500 MHz, DMSO-d6) δ 12.60 (s, 1H), 8.54 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.41 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.45 (s, 3H), 2.20 (s, 3H).
1-1151
1-1152				1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 7.97-7.89 (m, 2H), 7.40 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.45 (s, 3H), 2.37 (s, 3H).
1-1153
1-1154
1-1155				1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.35 (d, J = 5.0 Hz, 1H), 7.95-7.88 (m, 1H), 7.46 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.72 (s, 6H), 2.44 (s, 3H).
1-1156
1-1157	Et			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.54 (d, J = 5.0 Hz, 1H), 8.07-7.81 (m, 2H), 7.52-7.20 (m, 3H), 2.70 (q, J = 8.0 Hz, 2H), 2.45 (s, 3H), 1.07 (t, J = 8.0 Hz, 3H).
1-1158
1-1159	NO2			1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 7.95-7.87 (m, 2H), 7.62 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.47 (s, 3H).
1-1160	CN			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.98 (d, J = 5.0 Hz, 1H), 8.02-7.95 (m, 2H), 7.64 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.46 (s, 3H).
1-1161
1-1162
1-1163
1-1164
1-1165				1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 8.01-7.94 (m, 2H), 7.40 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.68 (s, 2H), 3.58 (q, J = 8.0 Hz, 2H), 2.45 (s, 3H), 1.18 (t, J = 8.0 Hz, 3H).
1-1166				1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.58 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.35-7.27 (m, 2H), 7.19 (d, J = 5.0 Hz, 1H), 6.62-6.48 (m, 1H), 5.48-5.36 (m, 1H), 5.30-5.22 (m, 1H), 2.43 (s, 3H).
1-1167
1-1168
1-1169
1-1170
1-1171				1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 7.98-7.91 (m, 2H), 7.57-7.47 (m, 3H), 7.35-7.27 (m, 2H), 7.23- 7.15 (m, 2H), 2.43 (s, 3H).
1-1172	Cl
1-1173	Cl
1-1174	Cl
1-1175	Cl
1-1176	Cl
1-1177	Cl
1-1178	Cl
1-1179	Cl
1-1180	Cl
1-1181	Cl
1-1182	Cl
1-1183	Cl
1-1184	Cl
1-1185	Cl
1-1186	Cl
1-1187	Cl
1-1188	Cl
1-1189	Cl
1-1190	Cl
1-1191	Cl
1-1192	Cl
1-1193	Cl
1-1194	Cl
1-1195	Cl
1-1196	Cl
1-1197	Cl
1-1198	Cl
1-1199	Cl
1-1200	Cl
1-1201	Cl
1-1202	Cl
1-1203	Cl
1-1204	Cl
1-1205	Cl
1-1206	Cl
1-1207	Cl
1-1208	Cl
1-1209	Cl
1-1210	Cl
1-1211	Cl
1-1212	Cl
1-1213	Cl
1-1214	Cl
1-1215	Cl
1-1216	Cl
1-1217	Cl
1-1218	Cl
1-1219	Cl
1-1220	Cl
1-1221	Cl
1-1222	Cl
1-1223	Cl
1-1224	Cl
1-1225	Cl
1-1226	Cl
1-1227	Cl
1-1228	Cl
1-1229	Cl
1-1230	Cl
1-1231	Cl
1-1232	Cl
1-1233	Cl
1-1234	Cl
1-1235	Cl
1-1236	Cl
1-1237	Cl
1-1238	Cl
1-1239	Cl
1-1240	Cl
1-1241	Cl
1-1242	Cl
1-1243	Cl
1-1244	Cl
1-1245	Cl
1-1246	Cl
1-1247	Cl
1-1248	Cl
1-1249	Cl
1-1250	Cl
1-1251	Cl
1-1252	Cl
1-1253	Cl
1-1254	Cl
1-1255	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.01 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.76 (s, 1H), 7.60 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H).
1-1256	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.02 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.78 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.08 (hept, J = 7.0 Hz, 1H), 1.26 (d, J = 7.0 Hz, 6H).
1-1257	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.75 (d, J = 4.5 Hz, 1H), 7.68-7.60 (m, 2H), 7.11-7.03 (m, 2H), 6.79 (d, J = 4.5 Hz, 1H), 1.50-1.35 (m, 1H), 1.02-0.96 (m, 2H), 0.94- 0.88 (m, 2H).
1-1258	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.70 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H).
1-1259	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.34-8.26 (m, 2H), 7.55 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H).
1-1260	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.79 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.70 (s, 2H), 2.10 (s, 3H).
1-1261	Cl			1H NMR (500 MHz, DMSO-d6) δ 13.02 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.15 (s, 2H), 8.01- 7.93 (m, 2H), 7.80 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H).
1-1262	Cl			1H NMR (500 MHz, DMSO-d6) δ 13.04 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.81 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.38 (s, 3H).
1-1263	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.78 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.48 (hept, J = 7.0 Hz, 1H), 1.21 (d, J = 7.0 Hz, 6H).
1-1264	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.34 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.89 (d, J = 5.0 Hz, 1H), 7.72 (s, 1H), 7.48 (d, J = 7.5 Hz, 1H), 7.42 (d, J = 7.5 Hz, 1H), 7.35- 7.27 (m, 2H).
1-1265	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.10-7.98 (m, 2H), 7.54 (d, J = 5.0 Hz, 1H), 7.37-7.19 (m, 4H), 6.72-6.95 (m, 1H), 6.90-6.80 (m, 2H).
1-1266	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.14 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 8.07-7.92 (m, 2H), 7.74-7.72 (m, 1H), 7.48 (d, J = 5.0 Hz, 1H), 7.37- 7.25 (m, 2H), 6.84-6.82 (m, 1H), 6.68 (t, J = 7.5 Hz, 1H).
1-1267	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.15 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 8.08-7.95 (m, 2H), 7.77 (d, J = 2.5, 1H), 7.66 (d, J = 2.5 Hz, 1H), 7.46 (d, J = 5.0 Hz, 1H), 7.37-7.25 (m, 2H), 6.66 (t, J = 2.5 Hz, 1H).
1-1268	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.10-7.96 (m, 2H), 7.79-7.62 (m, 2H), 7.58 (d, J = 5.0 Hz, 1H), 7.38- 7.20 (m, 4H), 4.07 (q, J = 8.0 Hz, 2H), 3.97 (t, J = 8.0 Hz, 3H).
1-1269	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.84 (d, J = 5.0 Hz, 1H), 8.07-7.92 (m, 2H), 7.56 (d, J = 5.0 Hz, 1H), 7.40-7.24 (m, 2H), 3.58-3.40 (m, 4H), 1.81-1.68 (m, 4H), 1.59-1.43 (m, 2H).
1-1270	Cl	CH3
1-1271	Cl
1-1272	Cl
1-1273	Cl
1-1274	Cl
1-1275	Cl
1-1276	Cl
1-1277	Cl
1-1278	Cl
1-1279	Cl
1-1280	Cl
1-1281	Cl
1-1282	Cl
1-1283	Cl
1-1284	Cl
1-1285	Cl
1-1286	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.53 (s, 1H), 8.79-8.73 (m, 2H), 7.64-7.57 (m, 2H), 7.33 (d, J = 4.5 Hz, 1H), 7.11-7.03 (m, 2H), 6.77 (d, J = 2.5 Hz, 1H).
1-1287	Cl
1-1288	Cl
1-1289	Cl
1-1290	Cl
1-1291	Cl
1-1292	Cl
1-1293	Cl
1-1294	Cl
1-1295	Cl
1-1296	Cl
1-1297	Cl
1-1298	Cl
1-1299	Cl
1-1300	Cl
1-1301	Cl
1-1302	Cl
1-1303	Cl
1-1304	Cl
1-1305	Cl
1-1306	Cl
1-1307	Cl
1-1308	Cl
1-1309	Cl
1-1310	Cl
1-1311	Cl
1-1312	Cl
1-1313	Cl
1-1314	Cl
1-1315	Cl
1-1316	Cl
1-1317	Cl
1-1318	Cl
1-1319	Cl
1-1320	Cl
1-1321	Cl
1-1322	Cl
1-1323	Cl
1-1324	Cl
1-1325	Cl
1-1326	Cl
1-1327	Cl
1-1328	Cl
1-1329	Cl
1-1330	Cl
1-1331	Cl
1-1332	Cl
1-1333	Cl
1-1334	Cl
1-1335	Cl
1-1336	Cl
1-1337	Cl
1-1338	Cl
1-1339	Cl
1-1340	Cl
1-1341	Cl
1-1342	Cl
1-1343	Cl
1-1344	Cl
1-1345	Cl
1-1346	Cl
1-1347	Cl
1-1348	Cl
1-1349	Cl
1-1350	Cl
1-1351	Cl
1-1352	Cl
1-1353	Cl
1-1354	Cl
1-1355	Cl
1-1356	Cl
1-1357	Cl
1-1358	Cl
1-1359	Cl
1-1360	Cl
1-1361	Cl
1-1362	Cl
1-1363	Cl
1-1364	Cl
1-1365	Cl
1-1366	Cl
1-1367	Cl
1-1368	Cl
1-1369	Cl
1-1370	Cl
1-1371	Cl
1-1372	Cl
1-1373	Cl
1-1374	Cl
1-1375	Cl
1-1376	Cl
1-1377	Cl
1-1378	Cl
1-1379	Cl
1-1380	Cl
1-1381	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.24 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 7.5 Hz, 1H), 8.54 (t, J = 1.5 Hz, 1H), 8.19 (dd, J = 7.5, 1.5 Hz, 1H), 8.14-7.92 (m, 3H), 7.88 (d, J = 5.0 Hz, 1H), 7.67-7.58 (m, 2H), 6.77 (d, J = 2.5 Hz, 1H).
1-1382	Cl
1-1383	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 9.26 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 5.5 Hz, 1H), 8.60-8.58 (m, 1H), 8.23 (dd, J = 7.5, 1.5 Hz, 1H), 8.17-8.14 (m, 1H), 7.87-7.82 (m, 2H), 7.66 (d, J = 2.5 Hz, 1H), 6.77 (d, J = 2.5 Hz, 1H).
1-1384	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.94-8.85 (m, 2H), 8.81-8.73 (m, 2H), 8.40 (d, J = 1.5 Hz, 1H), 8.20-8.13 (m, 1H), 8.05- 7.99 (m, 1H), 7.95-7.86 (m, 5H), 6.77 (d, J = 2.5 Hz, 1H).
1-1385	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 7.5 Hz, 1H), 8.21 (dd, J = 7.5, 1.5 Hz, 1H), 8.13-7.98 (m, 2H), 7.91 (d, J = 5.0 Hz, 1H), 7.66-7.58 (m, 2H), 7.44 (td, J = 7.5, 1.5 Hz, 1H), 7.38-7.22 (m, 1H), 6.77 (d, J = 7.5 Hz, 1H).
1-1386	Cl
1-1387	Cl
1-1388	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 7.5 Hz, 1H), 8.25-8.12 (m, 2H), 8.05-7.88 (m, 2H), 7.72- 7.62 (m, 2H), 7.60-7.55 (m, 1H), 7.48-7.21 (m, 1H), 6.77 (d, J = 2.5 Hz, 1H).
1-1389	Cl
1-1390	Cl
1-1391	Cl
1-1392	Cl
1-1393	Cl
1-1394	Cl
1-1395	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.18 (s, 1H), 8.90 (s, 1H), 8.77-8.61 (m, 2H), 8.46 (d, J = 5.0 Hz, 1H), 8.02 (d, J = 2.5 Hz, 1H), 7.43 (d, J = 5.0 Hz, 1H), 6.77 (d, J = 2.5 Hz, 1H), 2.42 (s, 3H).
1-1396	Cl
1-1397	Cl
1-1398	Cl
1-1399	Cl
1-1400	Cl
1-1401	Cl
1-1402	Cl
1-1403	Cl
1-1404	Cl
1-1405	Cl
1-1406	Cl
1-1407	Cl
1-1408	Cl
1-1409	Cl
1-1410	Cl
1-1411	Cl
1-1412	Cl
1-1413	Cl
1-1414	Cl
1-1415	Cl
1-1416	Cl
1-1417	Cl
1-1418	Cl
1-1419	Cl
1-1420	Cl
1-1421	Cl
1-1422	Cl
1-1423	Cl
1-1424	Cl
1-1425	Cl
1-1426	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.14 (s, 1H), 9.37-9.33 (m, 3H), 8.83 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 2.5 Hz, 1H), 7.99 (d, J = 5.0 Hz, 1H), 6.77 (d, J = 2.5 Hz, 1H).
1-1427	Cl
1-1428	Cl
1-1429	Cl
1-1430	Cl
1-1431	Cl
1-1432	Cl
1-1433	Cl
1-1434	Cl
1-1435	Cl
1-1436	Cl
1-1437	Cl
1-1438	Cl
1-1439	Cl
1-1440	Cl
1-1441	Cl
1-1442	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.17 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 2.5 Hz, 1H), 7.97 (d, J = 5.0 Hz, 1H), 7.80 (s, 1H), 6.97 (s, 1H), 6.77 (d, J = 2.5 Hz, 1H), 4.29 (q, J = 8.0 Hz, 2H), 1.16 (t, J = 8.0 Hz, 3H).
1-1443	Cl
1-1444	Cl
1-1445	Cl
1-1446	Cl
1-1447	Cl
1-1448	Cl
1-1449	Cl
1-1450	Cl
1-1451	Cl
1-1452	Cl
1-1453	Cl
1-1454	Cl
1-1455	Cl
1-1456	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.93 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 2.5 Hz, 1H), 8.03 (d, J = 5.0 Hz, 1H), 7.58 (d, J = 2.5 Hz, 1H), 7.47 (d, J = 4.0 Hz, 1H), 7.15-7.12 (m, 1H), 6.77 (d, J = 2.5 Hz, 1H).
1-1457	Cl
1-1458	Cl
1-1459	Cl
1-1460	Cl
1-1461	Cl
1-1462	Cl
1-1463	Cl
1-1464	CH3			1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.58 (d, J = 5.0 Hz, 1H), 7.98-7.90 (m, 2H), 7.85 (s, 1H), 7.49 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.51 (s, 3H), 2.35 (s, 3H).
1-1465	F
1-1466	Br
1-1467
1-1468	CF3			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.84 (s, 1H), 7.52 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.31 (s, 3H).
1-1469				1H NMR (500 MHz, DMSO-d6) δ 12.15 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.83 (s, 1H), 7.69-7.59 (m, 3H), 7.47-7.40 (m, 2H), 7.39-7.21 (m, 1H), 7.35-7.27 (m, 2H), 2.23 (s, 3H).
1-1470				1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.56 (d, J = 5.0 Hz, 1H), 8.09-8.01 (m, 2H), 7.85 (s, 1H), 7.50 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.67 (s, 3H), 2.31 (s, 3H).
1-1471
1-1472
1-1473
1-1474				1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.58 (d, J = 4.9 Hz, 1H), 8.03-7.96 (m, 2H), 7.85 (s, 1H), 7.47 (d, J = 4.9 Hz, 1H), 7.35-7.27 (m, 2H), 3.00 (q, J = 8.0 Hz, 2H), 2.31 (s, 3H), 1.19 (t, J = 8.0 Hz, 3H).
1-1475
1-1476				1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.14-8.06 (m, 2H), 7.86 (s, 1H), 7.54 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.63-2.61 (m, 1H), 2.59-2.56 (m, 1H), 2.31 (s, 3H), 1.22 (t, J = 8.0 Hz, 3H).
1-1477
1-1478				1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.38 (d, J = 5.0 Hz, 1H), 8.06-7.98 (m, 2H), 7.83 (s, 1H), 7.48 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.75 (s, 6H), 2.30 (s, 3H).
1-1479
1-1480	Et
1-1481
1-1482	NO2			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.96 (d, J = 5.0 Hz, 1H), 7.99-7.91 (m, 2H), 7.86 (s, 1H), 7.71 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.31 (s, 3H).
1-1483	CN			1H NMR (500 MHz, DMSO-d6) δ 12.13 (s, 1H), 9.01 (d, J = 5.0 Hz, 1H), 8.05-7.97 (m, 2H), 7.84 (s, 1H), 7.69 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.31 (s, 3H).
1-1484				1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.03-7.96 (m, 2H), 7.84 (s, 1H), 7.49 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.68 (s, 2H), 3.28 (s, 3H), 2.30 (s, 3H).
1-1485
1-1486
1-1487
1-1488
1-1489
1-1490				1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.01-7.94 (m, 2H), 7.80 (s, 1H), 7.53 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.31 (s, 1H), 2.39 (s, 3H).
1-1491
1-1492
1-1493
1-1494	Cl
1-1495	Cl
1-1496	Cl
1-1497	Cl
1-1498	Cl
1-1499	Cl
1-1500	Cl
1-1501	Cl
1-1502	Cl
1-1503	Cl
1-1504	Cl
1-1505	Cl
1-1506	Cl
1-1507	Cl
1-1508	Cl
1-1509	Cl
1-1510	Cl
1-1511	Cl
1-1512	Cl
1-1513	Cl
1-1514	Cl
1-1515	Cl
1-1516	Cl
1-1517	Cl
1-1518	Cl
1-1519	Cl
1-1520	Cl
1-1521	Cl
1-1522	Cl
1-1523	Cl
1-1524	Cl
1-1525	Cl
1-1526	Cl
1-1527	Cl
1-1528	Cl
1-1529	Cl
1-1530	Cl
1-1531	Cl
1-1532	Cl
1-1533	Cl
1-1534	Cl
1-1535	Cl
1-1536	Cl
1-1537	Cl
1-1538	Cl
1-1539	Cl
1-1540	Cl
1-1541	Cl
1-1542	Cl
1-1543	Cl
1-1544	Cl
1-1545	Cl
1-1546	Cl
1-1547	Cl
1-1548	Cl
1-1549	Cl
1-1550	Cl
1-1551	Cl
1-1552	Cl
1-1553	Cl
1-1554	Cl
1-1555	Cl
1-1556	Cl
1-1557	Cl
1-1558	Cl
1-1559	Cl
1-1560	Cl
1-1561	Cl
1-1562	Cl
1-1563	Cl
1-1564	Cl
1-1565	Cl
1-1566	Cl
1-1567	Cl
1-1568	Cl
1-1569	Cl
1-1570	Cl
1-1571	Cl
1-1572	Cl
1-1573	Cl
1-1574	Cl
1-1575	Cl
1-1576	Cl
1-1577	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 7.78 (s, 1H), 7.63-7.56 (m, 2H), 7.41 (d, J = 5.0 Hz, 1H), 7.11-7.03 (m, 2H), 2.31 (s, 3H).
1-1578	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.76 (s, 1H), 7.54 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.70 (q, J = 8.0 Hz, 2H), 1.25 (t, J = 8.0 Hz, 3H).
1-1579	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.34-8.26 (m, 2H), 8.10 (s, 1H), 7.55 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.46-2.32 (m, 1H), 1.12-1.02 (m, 2H), 0.85-0.69 (m, 2H).
1-1580	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.85 (s, 1H), 7.50 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.64 (s, 2H).
1-1581	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 3H), 7.52 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H).
1-1582	Cl			1H NMR (500 MHz, DMSO-d6) δ 11.99 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.51 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 6.82 (s, 1H), 4.63 (s, 2H), 3.33 (s, 3H).
1-1583	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.72 (s, 1H), 7.52 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H).
1-1584	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.43 (s, 1H), 10.68 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.04- 7.96 (m, 2H), 7.50 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 5.88 (s, 1H), 3.47 (q, J = 8.0 Hz, 2H), 1.07 (t, J = 8.0 Hz, 3H).
1-1585	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.11 (s, 1H), 8.07-7.99 (m, 2H), 7.65-7.58 (m, 3H), 7.58-7.52 (m, 2H), 7.35-7.27 (m, 2H).
1-1586	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 9.00 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.07-7.99 (m, 2H), 7.86-7.79 (m, 2H), 7.73-7.65 (m, 1H), 7.66-7.56 (m, 3H), 7.35-7.27 (m, 2H).
1-1587	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.24 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.73-8.58 (m, 1H), 8.07- 8.00 (m, 2H), 7.97 (dd, J = 8.0, 1.0 Hz, 1H), 7.86-7.69 (m, 1H), 7.63 (d, J = 5.0 Hz, 1H), 7.48-7.36 (m, 1H), 7.35-7.27 (m, 2H), 6.74 (s, 1H).
1-1588	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.30 (s, 1H), 8.05-7.97 (m, 2H), 7.70 (d, J = 2.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 7.19-7.09 (m, 2H).
1-1589	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.85 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.32 (s, 1H), 8.28 (s, 1H), 8.05-7.98 (m, 2H), 7.53 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H).
1-1590	Cl	CH3
1-1591	Cl
1-1592	Cl
1-1593	Cl
1-1594	Cl
1-1595	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 7.63 (d, J = 5.0 Hz, 1H), 7.44 (d, J = 2.5 Hz, 1H), 7.25 (d, J = 2.5 Hz, 1H), 6.42-6.36 (m, 1H), 4.34 (t, J = 6.0 Hz, 2H), 3.33-3.31 (m, 2H), 3.05-3.01 (m, 2H), 1.96 (s, 3H).
1-1596	Cl
1-1597	Cl
1-1598	Cl
1-1599	Cl
1-1600	Cl
1-1601	Cl
1-1602	Cl
1-1603	Cl
1-1604	Cl
1-1605	Cl
1-1606	Cl
1-1607	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.24 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.05-7.98 (m, 2H), 7.56-7.48 (m, 2H), 7.35-7.27 (m, 2H), 7.23 (d, J = 2.5 Hz, 1H).
1-1608	Cl
1-1609	Cl
1-1610	Cl
1-1611	Cl
1-1612	Cl
1-1613	Cl
1-1614	Cl
1-1615	Cl
1-1616	Cl
1-1617	Cl
1-1618	Cl
1-1619	Cl
1-1620	Cl
1-1621	Cl
1-1622	Cl
1-1623	Cl
1-1624	Cl
1-1625	Cl
1-1626	Cl
1-1627	Cl
1-1628	Cl
1-1629	Cl
1-1630	Cl
1-1631	Cl
1-1632	Cl
1-1633	Cl
1-1634	Cl
1-1635	Cl
1-1636	Cl
1-1637	Cl
1-1638	Cl
1-1639	Cl
1-1640	Cl
1-1641	Cl
1-1642	Cl
1-1643	Cl
1-1644	Cl
1-1645	Cl
1-1646	Cl
1-1647	Cl
1-1648	Cl
1-1649	Cl
1-1650	Cl
1-1651	Cl
1-1652	Cl
1-1653	Cl
1-1654	Cl
1-1655	Cl
1-1656	Cl
1-1657	Cl
1-1658	Cl
1-1659	Cl
1-1660	Cl
1-1661	Cl
1-1662	Cl
1-1663	Cl
1-1664	Cl
1-1665	Cl
1-1666	Cl
1-1667	Cl
1-1668	Cl
1-1669	Cl
1-1670	Cl
1-1671	Cl
1-1672	Cl
1-1673	Cl
1-1674	Cl
1-1675	Cl
1-1676	Cl
1-1677	Cl
1-1678	Cl
1-1679	Cl
1-1680	Cl
1-1681	Cl
1-1682	Cl
1-1683	Cl
1-1684	Cl
1-1685	Cl
1-1686	Cl
1-1687	Cl
1-1688	Cl
1-1689	Cl
1-1690	Cl
1-1691	Cl
1-1692	Cl
1-1693	Cl
1-1694	Cl
1-1695	Cl
1-1696	Cl
1-1697	Cl
1-1698	Cl
1-1699	Cl
1-1700	Cl
1-1701	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.39 (dd, J = 7.5, 2.0 Hz, 1H), 8.15-8.07 (m, 2H), 8.03-8.01 (m, 1H), 7.90 (t, J = 7.5 Hz, 1H), 7.64 (d, J = 5.0 Hz, 1H), 7.60-7.56 (m, 1H), 7.52-7.50 (m, 1H), 7.47 (d, J = 2.0 Hz, 1H), 7.25 (d, J = 2.0 Hz, 1H).
1-1702	Cl
1-1703	Cl
1-1704	Cl
1-1705	Cl
1-1706	Cl
1-1707	Cl
1-1708	Cl
1-1709	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.63 (s, 1H), 8.48 (dd, J = 7.5, 2.0 Hz, 1H), 8.15-8.10 (m, 2H), 8.07-8.04 (m, 1H), 7.61 (d, J = 5.0 Hz, 1H), 7.56-7.54 (m, 1H), 7.49-7.46 (m, 1H), 7.45 (d, J = 2.5 Hz, 1H), 7.25 (d, J = 2.5 Hz, 1H).
1-1710	Cl
1-1711	Cl
1-1712	Cl
1-1713	Cl
1-1714	Cl
1-1715	Cl
1-1716	Cl
1-1717	Cl
1-1718	Cl
1-1719	Cl
1-1720	Cl
1-1721	Cl
1-1722	Cl
1-1723	Cl
1-1724	Cl
1-1725	Cl
1-1726	Cl
1-1727	Cl
1-1728	Cl
1-1729	Cl
1-1730	Cl
1-1731	Cl
1-1732	Cl
1-1733	Cl
1-1734	Cl
1-1735	Cl
1-1736	Cl
1-1737	Cl
1-1738	Cl
1-1739	Cl
1-1740	Cl
1-1741	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 8.77 (d, J = 5.0 Hz, 1H), 8.13 (s, 1H), 8.02 (d, J = 5.0 Hz, 1H), 7.76 (d, J = 5.0 Hz, 1H), 7.43 (d, J = 2.5 Hz, 1H), 7.24 (d, J = 2.5 Hz, 1H).
1-1742	Cl
1-1743	Cl
1-1744	Cl
1-1745	Cl
1-1746	Cl
1-1747	Cl
1-1748	Cl
1-1749	Cl
1-1750	Cl
1-1751	Cl
1-1752	Cl
1-1753	Cl
1-1754	Cl
1-1755	Cl
1-1756	Cl
1-1757	Cl
1-1758	Cl
1-1759	Cl
1-1760	Cl
1-1761	Cl
1-1762	Cl
1-1763	Cl
1-1764	Cl
1-1765	Cl
1-1766	Cl
1-1767	Cl
1-1768	Cl
1-1769	Cl
1-1770	Cl
1-1771	Cl
1-1772	Cl
1-1773	Cl
1-1774	Cl
1-1775	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.75 (d, J = 5.0 Hz, 1H), 7.43 (d, J = 2.5 Hz, 1H), 7.26 (d, J = 2.5 Hz, 1H), 7.24 (d, J = 2.5 Hz, 1H), 6.69 (d, J = 2.5 Hz, 1H), 3.92 (s, 3H).
1-1776	Cl
1-1777	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.86 (d, J = 5.0 Hz, 1H), 8.07 (d, J = 2.0 Hz, 1H), 7.89 (d, J = 5.0 Hz, 1H), 7.50 (d, J = 2.5 Hz, 1H), 7.28-7.22 (m, 2H), 6.98 (t, J = 2.5 Hz, 1H).
1-1778	Cl
1-1779	Cl
1-1780	Cl
1-1781	Cl
1-1782	Cl
1-1783	Cl
1-1784	Cl
1-1785	Cl
1-1786	Cl
1-1787	CH3			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.57 (d, J = 5.0 Hz, 1H), 8.00-7.92 (m, 2H), 7.52 (d, J = 2.5 Hz, 1H), 7.38 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 7.22 (d, J = 2.5 Hz, 1H), 2.44 (s, 3H).
1-1788	F
1-1789	Br
1-1790
1-1791	CF3			1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.55-7.48 (m, 2H), 7.35-7.27 (m, 2H), 7.21 (d, J = 2.5 Hz, 1H).
1-1792				1H NMR (500 MHz, DMSO-d6) δ 12.13 (s, 1H), 8.97 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.67-7.61 (m, 3H), 7.49-7.35 (m, 4H), 7.35- 7.27 (m, 2H), 7.23 (d, J = 2.5 Hz, 1H).
1-1793
1-1794
1-1795				1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.53 (d, J = 5.0 Hz, 1H), 8.10-8.02 (m, 2H), 7.52 (d, J = 2.5 Hz, 1H), 7.45 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 7.21 (d, J = 2.5 Hz, 1H), 5.03 (s, 2H).
1-1796
1-1797				1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.55 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.46 (d, J = 5.0 Hz, 1H), 7.45 (d, J = 2.5 Hz, 1H), 7.35-7.27 (m, 2H), 7.25 (d, J = 2.5 Hz, 1H), 3.00 (q, J = 8.0 Hz, 2H), 1.19 (t, J = 8.0 Hz, 3H).
1-1798
1-1799				1H NMR (500 MHz, DMSO-d6) δ 12.34 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.04-7.96 (m, 2H), 7.52 (d, J = 5.0 Hz, 1H), 7.43 (d, J = 2.5 Hz, 1H), 7.35-7.27 (m, 2H), 7.24 (d, J = 7.5 Hz, 1H), 2.61-2.59 (m, 1H), 2.57-2.55 (m, 1H), 1.21 (t, J = 8.0 Hz, 3H).
1-1800
1-1801				1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.36 (d, J = 5.0 Hz, 1H), 8.07-8.00 (m, 2H), 7.47 (d, J = 5.0 Hz, 1H), 7.42 (d, J = 2.5 Hz, 1H), 7.35-7.27 (m, 2H), 7.24 (d, J = 2.5 Hz, 1H), 2.77 (s, 6H).
1-1802				1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.41 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.93 (d, J = 5.0 Hz, 1H), 7.51 (d, J = 2.5 Hz, 1H), 7.35-7.27 (m, 2H), 7.26 (d, J = 2.5 Hz, 1H), 2.35 (s, 6H).
1-1803	Et
1-1804
1-1805	NO2			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.97 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.73 (d, J = 5.0 Hz, 1H), 7.47 (d, J = 2.5 Hz, 1H), 7.34-7.29 (m, 2H), 7.27 (d, J = 2.5 Hz, 1H).
1-1806	CN			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 9.02 (d, J = 5.0 Hz, 1H), 8.05-7.98 (m, 2H), 7.69 (d, J = 5.0 Hz, 1H), 7.46 (d, J = 2.5 Hz, 1H), 7.37-7.27 (m, 2H), 7.25 (d, J = 2.5 Hz, 1H).
1-1807				1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.04-7.96 (m, 2H), 7.51 (d, J = 2.5 Hz, 1H), 7.47 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 7.20 (d, J = 2.5 Hz, 1H), 4.68 (s, 2H), 3.28 (s, 3H).
1-1808
1-1809
1-1810
1-1811
1-1812
1-1813
1-1814
1-1815
1-1816
1-1817	Cl
1-1818	Cl
1-1819	Cl
1-1820	Cl
1-1821	Cl
1-1822	Cl
1-1823	Cl
1-1824	Cl
1-1825	Cl
1-1826	Cl
1-1827	Cl
1-1828	Cl
1-1829	Cl
1-1830	Cl
1-1831	Cl
1-1832	Cl
1-1833	Cl
1-1834	Cl
1-1835	Cl
1-1836	Cl
1-1837	Cl
1-1838	Cl
1-1839	Cl
1-1840	Cl
1-1841	Cl
1-1842	Cl
1-1843	Cl
1-1844	Cl
1-1845	Cl
1-1846	Cl
1-1847	Cl
1-1848	Cl
1-1849	Cl
1-1850	Cl
1-1851	Cl
1-1852	Cl
1-1853	Cl
1-1854	Cl
1-1855	Cl
1-1856	Cl
1-1857	Cl
1-1858	Cl
1-1859	Cl
1-1860	Cl
1-1861	Cl
1-1862	Cl
1-1863	Cl
1-1864	Cl
1-1865	Cl
1-1866	Cl
1-1867	Cl
1-1868	Cl
1-1869	Cl
1-1870	Cl
1-1871	Cl
1-1872	Cl
1-1873	Cl
1-1874	Cl
1-1875	Cl
1-1876	Cl
1-1877	Cl
1-1878	Cl
1-1879	Cl
1-1880	Cl
1-1881	Cl
1-1882	Cl
1-1883	Cl
1-1884	Cl
1-1885	Cl
1-1886	Cl
1-1887	Cl
1-1888	Cl
1-1889	Cl
1-1890	Cl
1-1891	Cl
1-1892	Cl
1-1893	Cl
1-1894	Cl
1-1895	Cl
1-1896	Cl
1-1897	Cl
1-1898	Cl
1-1899	Cl
1-1900	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.34 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.54 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 7.25 (s, 1H), 2.65 (t, J = 8.0 Hz, 2H), 1.70-1.48 (m, 2H), 0.92 (t, J = 8.0 Hz, 3H).
1-1901	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.14 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.75 (d, J = 5.0 Hz, 1H), 7.36 (s, 1H), 7.35-7.27 (m, 2H).
1-1902	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.14 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.06-7.99 (m, 2H), 7.54 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 6.81 (s, 1H), 3.81 (s, 3H).
1-1903	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.24 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.70 (d, J = 5.0 Hz, 1H), 7.45 (s, 1H), 7.35- 7.27 (m, 2H), 2.40 (s, 3H).
1-1904	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.34-8.26 (m, 2H), 7.69 (d, J = 5.0 Hz, 1H), 7.55 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H).
1-1905	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.69 (s, 1H), 7.54 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 3.20 (s, 6H).
1-1906	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.04-7.96 (m, 2H), 7.74 (s, 1H), 7.55 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H).
1-1907	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.04-7.96 (m, 2H), 7.56 (d, J = 5.0 Hz, 1H), 7.46 (s, 1H), 7.35- 7.27 (m, 2H), 3.83 (s, 2H), 2.60 (s, 3H).
1-1908	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 10.52 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.06- 7.99 (m, 2H), 7.69 (s, 1H), 7.52 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.13 (s, 3H).
1-1909	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.66 (d, J = 5.5 Hz, 2H), 8.05-8.01 (m, 2H), 7.99 (d, J = 5.5, 2H), 7.79 (s, 1H), 7.71 (d, J = 5.0 H,z 1H), 7.35- 7.27 (m, 2H).
1-1910	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 8.20-8.13 (m, 2H), 7.90 (s, 1H), 7.66 (d, J = 5.0 Hz, 1H), 7.64-7.60 (m, 2H), 7.55-7.51 (m, 2H), 7.35-7.27 (m, 2H).
1-1911	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.05-7.98 (m, 2H), 7.54 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 7.22 (s, 1H), 5.08 (t, J = 7.0 Hz, 1H), 3.90-3.79 (m, 2H), 2.26-2.11 (m, 2H), 1.88-1.76 (m, 2H).
1-1912	OMe	CH3		1H NMR (500 MHz, DMSO-d6) δ 12.84 (s, 1H), 8.62 (d, J = 5.0 Hz, 1H), 7.90 (d, J = 5.0 Hz, 1H), 3.74 (s, 3H), 2.51 (s, 3H), 2.46 (s, 3H).
1-1913	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 7.78 (d, J = 5.0 Hz, 1H), 6.99-6.94 (m, 1H), 6.13-6.09 (m, 1H), 5.63-5.59 (m, 1H), 4.33 (s, 3H).
1-1914	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.33 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.77 (d, J = 5.0 Hz, 1H), 4.38 (s, 3H), 3.70 (t, J = 6.0 Hz, 2H), 2.43 (t, J = 7.5 Hz, 2H), 2.11-2.06 (m, 2H).
1-1915	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.74-7.70 (m, 2H), 7.49 (d, J = 5.0 Hz, 1H), 7.27-7.23 (m, 2H), 4.31 (s, 3H), 2.74-2.69 (m, 2H), 1.19 (t, J = 8.0 Hz, 3H).
1-1916	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.29 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.72-7.69 (m, 2H), 7.47 (d, J = 5.0 Hz, 1H), 7.40-7.37 (m, 2H), 4.36 (s, 3H), 2.89-2.84 (m, 1H), 1.20 (d, J = 7.0 Hz, 6H).
1-1917	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.35 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.88-7.85 (m, 1H), 7.81-7.79 (m, 1H), 7.63-7.60 (m, 1H), 7.47 (d, J = 5.0 Hz, 1H), 7.34-7.31 (m, 1H), 4.39 (s, 3H), 2.63 (t, J = 5.5 Hz, 2H), 1.56-1.51 (m, 2H), 1.32-1.28 (m, 2H), 0.89 (t, J = 8.0 Hz, 3H).
1-1918	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.22 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.71-7.68 (m, 2H), 7.48-7.45 (m, 3H), 6.73-6.70 (m, 1H), 5.96- 5.93 (m, 1H), 5.71-5.68 (m, 1H), 4.32 (s, 3H).
1-1919	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.30 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 7.81-7.75 (m, 2H), 7.65-7.59 (m, 2H), 7.52 (d, J = 5.0 Hz, 1H), 6.45 (t, J = 57.0 Hz, 1H), 4.32 (s, 3H).
1-1920	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.26 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 8.02 (s, 1H), 7.88-7.85 (m, 1H), 7.68-7.65 (m, 1H), 7.59-7.57 (m, 1H), 7.48 (d, J = 5.0 Hz, 1H), 4.99 (s, 2H), 4.33 (s, 3H).
1-1921	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.80-7.77 (m, 2H), 7.48 (d, J = 5.0 Hz, 1H), 7.04-7.01 (m, 2H), 4.38 (s, 3H), 3.99 (t, J = 7.5 Hz, 2H), 1.78-1.71 (m, 2H), 0.98 (t, J = 8.0 Hz, 3H).
1-1922	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.22 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 7.85-7.79 (m, 2H), 7.55-7.49 (m, 3H), 4.39 (s, 3H), 2.45 (s, 3H).
1-1923	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.29 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.68-7.65 (m, 2H), 7.47 (d, J = 5.0 Hz, 1H), 7.21-7.17 (m, 2H), 4.38 (s, 3H).
1-1924	Cl
1-1925	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 7.89-7.82 (m, 2H), 7.54 (d, J = 5.0 Hz, 1H), 7.51-7.45 (m, 2H), 4.30 (s, 3H), 2.87 (s, 6H).
1-1926	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.29 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 7.73-7.70 (m, 2H), 7.53-7.50 (m, 1H), 7.16-7.14 (m, 1H), 4.31 (s, 3H), 2.27 (s, 3H), 2.23 (s, 3H).
1-1927	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.29 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.65 (d, J = 5.0 Hz, 1H), 7.53-7.50 (m, 1H), 7.33-7.26 (m, 2H), 4.38 (s, 3H).
1-1928	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.28 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.88-7.85 (m, 1H), 7.56-7.53 (m, 1H), 7.47 (d, J = 5.0 Hz, 1H), 7.22-7.19 (m, 1H), 4.39 (s, 3H).
1-1929	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.23 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.65-7.62 (m, 2H), 7.54-7.51 (m, 1H), 7.27-7.23 (m, 1H), 4.38 (s, 3H).
1-1930	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 7.69-7.62 (m, 2H), 7.62-7.59 (m, 1H), 7.53 (d, J = 5.0 Hz, 1H), 4.25 (s, 3H).
1-1931	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.27 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.60-7.57 (m, 1H), 7.49 (d, J = 5.0 Hz, 1H), 7.19-7.16 (m, 1H), 7.12-7.09 (m, 1H), 4.29 (s, 3H), 2.37 (s, 3H).
1-1932	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.74 (d, J = 7.5 Hz, 1H), 7.68 (d, J = 5.0 Hz, 1H), 7.56-7.53 (m, 1H), 7.10-7.07 (m, 1H), 4.30 (s, 3H), 2.31 (s, 3H).
1-1933	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.20 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.75 (s, 1H), 7.67- 7.64 (m, 2H), 6.94 (d, J = 7.5 Hz, 1H), 4.39 (s, 3H), 3.74 (s, 3H), 2.15 (s, 3H).
1-1934	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.73 (d, J = 6.0 Hz, 1H), 8.10 (s, 1H), 8.02 (s, 1H), 7.75 (s, 1H), 7.56 (d, J = 5.0 Hz, 1H), 4.29 (s, 3H), 2.32 (s, 3H).
1-1935	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.26 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.07 (d, J = 2.0 Hz, 1H), 7.72 (dd, J = 7.5, 2.0 Hz, 1H), 7.54 (d, J = 5.0 Hz, 1H), 7.38 (d, J = 7.5 Hz, 1H), 4.37 (s, 3H), 2.25 (s, 3H).
1-1936	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.33 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.11 (d, J = 2.0 Hz, 1H), 7.96 (dd, J = 7.5, 2.0 Hz, 1H), 7.52 (d, J = 5.0 Hz, 1H), 7.45 (d, J = 7.5 Hz, 1H), 4.33 (s, 3H), 2.45 (s, 3H).
1-1937	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.28 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.08 (d, J = 7.5 Hz, 1H), 7.76-7.72 (m, 1H), 7.61-7.55 (m, 2H), 4.29 (s, 3H), 2.39 (s, 3H).
1-1938	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.23 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.05-7.98 (m, 2H), 7.74 (d, J = 5.0 Hz, 1H), 7.71 (d, J = 7.5 Hz, 1H), 4.35 (s, 3H), 2.45 (s, 3H).
1-1939	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 8.27 (dd, J = 7.5, 2.0 Hz, 1H), 7.74 (dd, J = 7.5, 2.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 7.40 (dd, J = 7.5, 7.5 Hz, 1H), 4.36 (s, 3H), 2.45 (s, 3H).
1-1940	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.27 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.96-7.92 (m, 1H), 7.68-7.65 (m, 1H), 7.48-7.43 (m, 2H), 4.30 (s, 3H).
1-1941	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.29 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 7.91-7.87 (m, 2H), 7.65 (d, J = 5.0 Hz, 1H), 7.53-7.50 (m, 1H), 4.37 (s, 3H).
1-1942	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.31 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 8.20 (s, 1H), 8.06-8.03 (m, 1H), 7.66 (d, J = 5.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 4.35 (s, 3H).
1-1943	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.24 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 8.17-8.14 (m, 1H), 7.61-7.55 (m, 2H), 7.49 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H).
1-1944	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.29 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 7.88 (s, 1H), 7.74- 7.70 (m, 2H), 7.59 (s, 1H), 4.35 (s, 3H).
1-1945	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.31 (s, 1H), 8.62 (d, J = 5.0 Hz, 1H), 7.81-7.78 (m, 1H), 7.46 (d, J = 5.0 Hz, 1H), 6.79-6.76 (m, 1H), 6.74-6.72 (m, 1H), 4.31 (s, 3H), 3.76 (s, 3H).
1-1946	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.47-7.44 (m, 2H), 7.25-7.22 (m, 2H), 4.35 (s, 3H), 3.80 (s, 3H).
1-1947	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.29 (s, 1H), 8.62 (d, J = 5.0 Hz, 1H), 7.78-7.75 (m, 1H), 7.63 (d, J = 5.0 Hz, 1H), 6.92-6.89 (m, 1H), 6.80-6.77 (m, 1H), 4.38 (q, J = 8.0 Hz, 2H), 4.35 (s, 3H), 1.45 (t, J = 8.0 Hz, 3H).
1-1948	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.24 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.48-7.44 (m, 2H), 7.05-7.01 (m, 1H), 6.90-6.87 (m, 1H), 4.39 (s, 3H), 3.70 (d, J = 7.0 Hz, 2H), 2.01-1.92 (m, 1H), 0.95 (d, J = 7.0 Hz, 6H).
1-1949	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.29 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.94 (s, 1H), 7.65 (d, J = 5.0 Hz, 1H), 7.48 (d, J = 7.5 Hz, 1H), 6.93 (d, J = 7.5 Hz, 1H), 4.33 (s, 3H), 3.85 (s, 3H).
1-1950	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.26 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.79 (dd, J = 7.5, 2.0 Hz, 1H), 7.67-7.63 (m, 2H), 7.55 (d, J = 7.5 Hz, 1H), 4.31 (s, 3H), 4.10 (q, J = 8.0 Hz, 2H), 1.34 (t, J = 8.0 Hz, 3H).
1-1951	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.27 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 7.82 (s, 1H), 7.78 (d, J = 5.0 Hz, 1H), 7.65-7.62 (m, 1H), 7.48-7.44 (m, 2H), 7.39-7.35 (m, 2H), 7.32-7.29 (m, 2H), 5.15 (s, 2H), 4.35 (s, 3H).
1-1952	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.28 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 7.73-7.70 (m, 2H), 7.63 (dd, J = 7.5, 2.0 Hz, 1H), 7.22 (d, J = 7.5 Hz, 1H), 4.32 (s, 3H), 3.94 (s, 3H), 3.79 (s, 3H).
1-1953	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.31 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.43 (d, J = 2.0 Hz, 1H), 8.32 (dd, J = 7.5, 2.0 Hz, 1H), 7.81 (d, J = 7.5 Hz, 1H), 7.54 (d, J = 5.0 Hz, 1H), 4.30 (s, 3H).
1-1954	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.27 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.46 (s, 1H), 8.25- 8.22 (m, 2H), 7.54 (d, J = 5.0 Hz, 1H), 4.39 (s, 3H).
1-1955	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.29 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.17 (d, J = 2.0 Hz, 1H), 8.04 (dd, J = 7.5, 2.0 Hz, 1H), 7.83 (d, J = 7.5 Hz, 1H), 7.55 (d, J = 5.0 Hz, 1H), 4.38 (s, 3H).
1-1956	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.24 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.09 (d, J = 2.0 Hz, 1H), 8.05 (dd, J = 7.5, 2.0 Hz, 1H), 7.74 (d, J = 7.5 Hz, 1H), 7.57 (d, J = 5.0 Hz, 1H), 4.38 (s, 3H).
1-1957	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.24 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.25 (s, 1H), 7.98 (s, 1H), 7.92 (s, 1H), 7.69 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H).
1-1958	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.23 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.18 (dd, J = 7.5, 2.0 Hz, 1H), 8.10 (d, J = 2.0 Hz, 1H), 7.70 (d, J = 7.5 Hz, 1H), 7.53 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H).
1-1959	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.32 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.78 (s, 1H), 7.53 (d, J = 5.0 Hz, 1H), 7.49 (s, 1H), 7.42 (s, 1H), 4.31 (s, 3H), 3.79 (s, 3H).
1-1960	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.01 (d, J = 2.0 Hz, 1H), 7.79 (dd, J = 7.5, 2.0 Hz, 1H), 7.70 (d, J = 5.0 Hz, 1H), 7.15 (d, J = 7.5 Hz, 1H), 4.39 (s, 3H), 3.85 (s, 3H).
1-1961	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.19 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.44 (dd, J = 7.5, 2.0 Hz, 1H), 7.82 (dd, J = 7.5, 2.0 Hz, 1H), 7.54 (d, J = 5.0 Hz, 1H), 7.37 (dd, J = 7.5, 7.5 Hz, 1H), 4.34 (s, 3H), 3.84 (s, 3H).
1-1962	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.26 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.46 (dd, J = 7.5, 2.0 Hz, 1H), 8.34 (d, J = 2.0 Hz, 1H), 7.98 (d, J = 7.5 Hz, 1H), 7.71 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H).
1-1963	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.29 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.38 (d, J = 2.0 Hz, 1H), 8.11 (dd, J = 7.5, 2.0 Hz, 1H), 7.53 (d, J = 5.0 Hz, 1H), 7.36 (d, J = 7.5 Hz, 1H), 4.34 (s, 3H).
1-1964	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.29 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 7.94 (dd, J = 7.5, 2.0 Hz, 1H), 7.87 (d, J = 2.0 Hz, 1H), 7.76 (d, J = 7.5 Hz, 1H), 7.54 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H).
1-1965	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.23 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.08 (d, J = 2.0 Hz, 1H), 7.89 (dd, J = 7.5, 2.0 Hz, 1H), 7.52 (d, J = 5.0 Hz, 1H), 7.43 (d, J = 7.5 Hz, 1H), 4.30 (s, 3H).
1-1966	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.26 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.16 (s, 1H), 7.54 (d, J = 5.0 Hz, 1H), 7.28 (s, 1H), 4.35 (s, 3H), 2.37 (s, 3H).
1-1967	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.28 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 7.88 (d, J = 10.0 Hz, 1H), 7.74 (d, J = 6.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 4.35 (s, 3H), 2.43 (s, 3H).
1-1968	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.27 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.87 (s, 2H), 7.49 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H).
1-1969	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.23 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.64 (d, J = 5.0 Hz, 1H), 7.56-7.53 (m, 1H), 7.00-6.97 (m, 1H), 4.34 (s, 3H), 3.84 (s, 3H).
1-1970	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.26 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 7.71 (d, J = 5.0 Hz, 1H), 7.68-7.61 (m, 2H), 4.35 (s, 3H).
1-1971	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.50 (d, J = 5.0 Hz, 1H), 7.36 (s, 2H), 4.31 (s, 3H), 3.82 (s, 6H), 3.73 (s, 3H).
1-1972	Cl			1H NMR (500 MHz, DMSO-d6) δ 9.25 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 7.86 (dd, J = 7.5, 2.0 Hz, 1H), 7.52 (d, J = 5.0 Hz, 1H), 7.13 (dd, J = 7.5, 2.0 Hz, 1H), 7.01-6.98 (m, 1H), 4.33 (s, 3H).
1-1973	Cl
1-1974	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.23 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 7.95 (d, J = 5.0 Hz, 1H), 7.74 (d, J = 5.0 Hz, 1H), 7.60 (s, 1H), 7.28 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.89 (s, 3H).
1-1975	Cl
1-1976	Cl
1-1977	Cl
1-1978	Cl
1-1979	Cl
1-1980	Cl
1-1981	Cl
1-1982	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.22 (s, 1H), 8.78 (d, J = 5.0 Hz, 1H), 8.58 (d, J = 5.0 Hz, 1H), 7.78 (d, J = 5.0 Hz, 1H), 7.63 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H), 2.60 (s, 3H), 2.21 (s, 3H).
1-1983	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.29 (s, 1H), 8.78 (d, J = 5.0 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 7.64 (s, 2H), 4.39 (s, 3H), 2.55 (s, 6H).
1-1984	Cl
1-1985	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.26 (s, 1H), 8.81 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.18 (s, 1H), 7.87 (d, J = 5.0 Hz, 1H), 4.36 (s, 3H), 2.32 (s, 3H).
1-1986	Cl
1-1987	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 8.26 (d, J = 5.0 Hz, 1H), 7.92 (d, J = 5.0 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 4.38 (s, 3H), 2.30 (s, 3H).
1-1988	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.24 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 8.42 (s, 1H), 8.33 (s, 1H), 7.78 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H), 2.28 (s, 3H).
1-1989	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.30 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.62 (s, 1H), 8.25 (d, J = 5.0 Hz, 1H), 7.87 (d, J = 5.0 Hz, 1H), 4.35 (s, 3H), 2.30 (s, 3H).
1-1990	Cl
1-1991	Cl
1-1992	Cl
1-1993	Cl
1-1994	Cl
1-1995	Cl
1-1996	Cl
1-1997	Cl
1-1998	Cl
1-1999	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.27 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 7.89 (d, J = 5.0 Hz, 1H), 6.80 (d, J = 4.5 Hz, 1H), 6.09 (d, J = 4.5 Hz, 1H), 4.35 (s, 3H), 2.35 (s, 3H).
1-2000	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 9.25 (s, 1H), 8.93 (d, J = 5.0 Hz, 1H), 7.92 (d, J = 5.0 Hz, 1H), 7.67 (s, 1H), 6.88 (s, 1H), 4.33 (s, 3H).
1-2001	Cl			1H NMR (500 MHz, DMSO-d6) δ 11.51 (s, 1H), 8.97 (d, J = 5.0 Hz, 1H), 8.04 (d, J = 5.0 Hz, 1H), 7.74-7.71 (m, 2H), 7.33 (d, J = 4.5 Hz, 1H), 6.74 (s, 1H), 2.41 (s, 3H).
1-2002	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.28 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 7.60 (d, J = 4.5 Hz, 1H), 7.27 (d, J = 4.5 Hz, 1H), 4.33 (s, 3H), 2.31 (s, 3H).
1-2003	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.93 (d, J = 5.0 Hz, 1H), 8.10 (s, 1H), 7.80 (d, J = 5.0 Hz, 1H), 7.68 (s, 1H), 4.33 (s, 3H).
1-2004	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.30 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 7.96 (d, J = 5.0 Hz, 1H), 7.85 (s, 1H), 7.42 (d, J = 4.5 Hz, 1H), 7.18 (d, J = 4.5 Hz, 1H), 4.51 (s, 2H), 4.33 (s, 3H), 1.39 (s, 9H).
1-2005	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 7.94 (d, J = 5.0 Hz, 1H), 7.86-7.78 (m, 2H), 7.60 (d, J = 7.5 Hz, 1H), 7.51-7.45 (m, 3H), 7.34 (d, J = 7.5 Hz, 1H), 4.36 (s, 3H).
1-2006	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.27 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 7.72 (d, J = 5.0 Hz, 1H), 7.03 (d, J = 4.5 Hz, 1H), 6.81 (d, J = 4.5 Hz, 1H), 6.35-6.31 (m, 1H), 4.36 (s, 3H).
1-2007	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.28 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.74 (d, J = 5.0 Hz, 1H), 7.60 (d, J = 3.5 Hz, 1H), 6.69 (d, J = 3.5 Hz, 1H), 4.60-4.56 (m, 1H), 4.32 (s, 3H), 1.27 (d, J = 7.0 Hz, 6H).
1-2008	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.22 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 7.91 (d, J = 4.5 Hz, 1H), 7.80 (d, J = 5.0 Hz, 1H), 7.59 (d, J = 4.5 Hz, 1H), 6.58-6.53 (m, 1H), 4.30 (s, 3H).
1-2009	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 7.80 (d, J = 5.0 Hz, 1H), 6.14 (s, 1H), 4.32 (s, 3H), 2.75 (s, 3H), 2.24 (s, 3H).
1-2010	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.27 (s, 1H), 8.80 (d, J = 5.0 Hz, 1H), 7.75 (d, J = 5.0 Hz, 1H), 7.67 (dd, J = 7.5, 1.5 Hz, 1H), 7.61 (dd, J = 7.5, 1.5 Hz, 1H), 7.42-7.38 (m, 1H), 7.30- 7.23 (m, 2H), 4.33 (s, 3H).
1-2011	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.26 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 8.58-8.56 (m, 1H), 8.49-8.47 (m, 1H), 8.10-8.07 (m, 1H), 8.05-8.02 (m, 1H), 7.83 (d, J = 5.0 Hz, 1H), 7.73-7.69 (m, 1H), 7.57-7.54 (m, 1H), 7.49-7.46 (m, 1H), 4.32 (s, 3H).
1-2012	F	CH3		1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.46 (d, J = 5.0 Hz, 1H), 7.50-7.47 (m, 1H), 4.33 (s, 3H), 2.54 (s, 3H).
1-2013	F			1H NMR (500 MHz, DMSO-d6) δ 12.27 (s, 1H), 8.30 (d, J = 5.0 Hz, 1H), 7.82 (dd, J = 7.0, 5.0 Hz, 1H), 4.33 (s, 3H), 1.77-1.72 (m, 1H), 0.84-0.79 (m, 2H), 0.71-0.65 (m, 2H).
1-2014	F			1H NMR (500 MHz, DMSO-d6) δ 12.29 (s, 1H), 8.35 (d, J = 5.0 Hz, 1H), 7.81 (dd, J = 7.0, 5.0 Hz, 1H), 4.34 (s, 3H), 3.70 (t, J = 6.0 Hz, 2H), 2.43 (t, J = 7.0 Hz, 2H), 2.09-2.02 (m, 2H).
1-2015	F			1H NMR (500 MHz, DMSO-d6) δ 12.28 (s, 1H), 8.45 (d, J = 5.0 Hz, 1H), 7.95-7.89 (m, 2H), 7.81 (dd, J = 7.0, 5.0 Hz, 1H), 7.51-7.45 (m, 2H), 4.37 (s, 3H).
1-2016	F			1H NMR (500 MHz, DMSO-d6) δ 12.26 (s 1H), 8.47 (d, J = 5.0 Hz, 1H), 8.18-8.12 (m, 2H), 7.84 (dd, J = 6.0, 5.0 Hz, 1H), 7.77-7.71 (m, 2H), 4.38 (s, 3H).
1-2017	F			1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 9.06 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 8.41 (d, J = 5.0 Hz, 1H), 8.31 (d, J = 8.0 H,z 1H), 8.16 (d, J = 5.0 Hz, 1H), 7.46 (dd, J = 8.0, 5.0 Hz, 1H), 4.34 (s, 3H).
1-2018	F			1H NMR (500 MHz, DMSO-d6) δ 12.26 (s, 1H), 8.90 (s, 1H), 8.54 (d, J = 5.0 Hz, 1H), 8.09- 8.01 (m, 2H), 7.47 (d, J = 8.0 Hz, 1H), 4.30 (s, 3H).
1-2019	F			1H NMR (500 MHz, DMSO-d6) δ 12.26 (s, 1H), 8.73 (s, 1H), 8.56 (d, J = 5.0 Hz, 1H), 8.37- 8.28 (m, 2H), 8.07 (d, J = 7.0 Hz, 1H), 4.32 (s, 3H).
1-2020	F			1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.57 (d, J = 5.0 Hz, 1H), 8.22 (d, J = 5.0 Hz, 1H), 8.09 (dd, J = 7.0, 5.0 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.89 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H).
1-2021	F			1H NMR (500 MHz, DMSO-d6) δ 12.33 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.14-8.10 (m, 1H), 7.90 (s, 1H), 7.00 (s, 1H), 4.35 (s, 3H), 3.93 (s, 3H).
1-2022	F			1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 8.05 (dd, J = 7.0, 5.0 Hz, 1H), 7.98-7.62 (m, 2H), 7.04 (s, 1H), 4.35 (s, 3H).
1-2023	OH			1H NMR (500 MHz, DMSO-d6) δ 12.22 (s, 1H), 8.38 (d, J = 5.0 Hz, 1H), 7.89-7.86 (m, 3H), 7.35- 7.27 (m, 2H), 4.38 (s, 3H).
1-2024	OMe			1H NMR (500 MHz, DMSO-d6) δ 12.22 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 8.05 (d, J = 5.0 Hz, 1H), 6.86-6.82 (m, 1H), 6.17-6.13 (m 1H), 5.68-5.64 (m, 1H), 4.32 (s, 3H), 3.79 (s, 3H).
1-2025	OMe			1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.43 (d, J = 5.0 Hz, 1H), 7.89 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.83 (s, 3H), 1.78-1.74 (m, 1H), 0.84-0.77 (m, 2H), 0.72-0.65 (m, 2H).
1-2026	OMe			1H NMR (500 MHz, DMSO-d6) δ 12.28 (s, 1H), 8.84 (d, J = 5.0 Hz, 1H), 8.16 (d, J = 5.0 Hz, 1H), 7.88 (s, 1H), 7.03 (s, 1H), 4.32 (s, 3H), 3.93 (s, 3H), 3.82 (s, 3H).
1-2027	OMe			1H NMR (500 MHz, DMSO-d6) δ 12.26 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.18 (d, J = 5.0 Hz, 1H), 7.62 (d, J = 4.5 Hz, 1H), 7.12 (d, J = 4.5 Hz, 1H), 4.31 (s, 3H), 3.79 (s, 3H), 2.39 (s, 3H).
1-2028	OMe			1H NMR (500 MHz, DMSO-d6) δ 12.30 (s, 1H), 8.59 (d, J = 5.0 Hz, 1H), 7.84-7.78 (m, 2H), 7.51-7.42 (m, 3H), 4.35 (s, 3H), 3.68 (s, 3H).
1-2029	OMe			1H NMR (500 MHz, DMSO-d6) δ 12.28 (s, 1H), 8.57 (d, J = 5.0 Hz, 1H), 8.17-8.10 (m, 2H), 7.87 (d, J = 5.0 Hz, 1H), 7.77-7.71 (m, 2H), 4.36 (s, 3H), 3.71 (s, 3H).
1-2030	OMe			1H NMR (500 MHz, DMSO-d6) δ 12.29 (s, 1H), 9.06 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.41 (d, J = 5.0 Hz, 1H), 8.30 (d, J = 8.0 Hz, 1H), 8.18 (d, J = 5.0 Hz, 1H), 7.46 (dd, J = 8.0, 5.0 Hz, 1H), 4.33 (s, 3H), 3.72 (s, 3H).
1-2031	OMe			1H NMR (500 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.79 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.93 (d, J = 8.0, Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 4.33 (s, 3H), 3.53 (s, 3H).
1-2032	OMe			1H NMR (500 MHz, DMSO-d6) δ 12.30 (s, 1H), 8.72-8.63 (m, 2H), 8.32 (d, J = 8.0 Hz, 1H), 8.20 (d, J = 9.0 Hz, 1H), 7.65 (d, J = 5.0 Hz, 1H), 4.38 (s, 3H), 3.58 (s, 3H).
1-2033	OMe
1-2034	OMe
1-2035	OMe			1H NMR (500 MHz, DMSO-d6) δ 12.29 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 7.83 (t, J = 57.0 Hz, 1H), 7.70 (s, 1H), 7.58 (d, J = 5.0 H, 1H), 6.96 (s, 1H), 4.33 (s, 3H), 2.59 (s, 3H).
1-2036
1-2037
1-2038				1H NMR (500 MHz, DMSO-d6) δ 12.31 (s, 1H), 8.55 (d, J = 5.0 Hz, 1H), 8.12 (d, J = 5.0 Hz, 1H), 6.78 (dd, J = 17.0, 10.0 Hz, 1H), 6.06 (dd, J = 14.0, 10.0 Hz, 1H), 5.95 (s, 1H), 5.58 (dd, J = 17.0, 14.0 Hz, 1H), 4.33 (s, 3H), 2.71 (s, 3H).
1-2039				1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.92 (s, 1H), 8.51 (d, J = 5.0 Hz, 1H), 8.41 (d, J = 5.0 Hz, 1H), 8.24 (d, J = 5.0 Hz, 1H), 8.20 (d, J = 8.0 Hz, 1H), 7.46 (dd, J = 8.0, 5.0 Hz, 1H), 5.95 (s, 1H), 4.29 (s, 3H), 2.64 (s, 3H).
1-2040				1H NMR (500 MHz, DMSO-d6) δ 12.31 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 8.24 (d, J = 5.0 Hz, 1H), 7.75 (s, 1H), 6.87 (s, 1H), 5.95 (s, 1H), 4.38 (s, 3H), 3.92 (s, 3H), 2.72 (s, 3H).
1-2041		CH3		1H NMR (500 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.46 (d, J = 5.0 Hz, 1H), 8.04 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 2.92 (s, 6H), 2.56 (s, 3H).
1-2042		CH2CH3		1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.44 (d, J = 5.0 Hz, 1H), 8.08 (d, J = 5.0 Hz, 1H), 4.36 (s, 3H), 3.13 (q, J = 8.0 Hz, 2H), 2.89 (s, 6H), 1.18 (t, J = 8.0 Hz, 3H).
1-2043				1H NMR (500 MHz, DMSO-d6) δ 12.26 (s, 1H), 8.59 (d, J = 5.0 Hz, 1H), 8.17 (d, J = 5.0 Hz, 1H), 6.73 (dd, J = 17.0, 10.0 Hz, 1H), 6.10 (dd, J = 14.0, 10.0 Hz, 1H), 5.60 (dd, J = 17.0, 14.0 Hz, 1H), 4.33 (s, 3H), 2.91 (s, 6H).
1-2044				1H NMR (500 MHz, DMSO-d6) δ 12.28 (s, 1H), 8.44 (d, J = 5.0 Hz, 1H), 8.01 (d, J = 5.0 Hz, 1H), 7.61-7.54 (m, 2H), 7.24-7.17 (m, 2H), 4.37 (s, 3H), 2.80 (s, 6H).
1-2045				1H NMR (500 MHz, DMSO-d6) δ 12.26 (s, 1H), 8.88 (s, 1H), 8.54 (d, J = 5.0 Hz, 1H), 8.41 (d, J = 5.0 Hz, 1H), 8.25 (d, J = 5.0 Hz, 1H), 8.15 (d, J = 8.0 Hz, 1H), 7.46 (dd, J = 8.0, 5.0 Hz, 1H), 4.39 (s, 3H), 2.82 (s, 6H).
1-2046				1H NMR (500 MHz, DMSO-d6) δ 12.91 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.26 (d, J = 5.0 Hz, 1H), 7.48 (d, J = 7.5 Hz, 1H), 7.10 (d, J = 7.5 Hz, 1H), 4.35 (s, 3H), 2.93 (s, 6H), 2.38 (s, 3H).
1-2047				1H NMR (500 MHz, DMSO-d6) δ 12.26 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.27 (d, J = 5.0 Hz, 1H), 7.70 (s, 1H), 6.82 (s, 1H), 4.33 (s, 3H), 3.92 (s, 3H), 2.95 (s, 6H).
1-2048				1H NMR (500 MHz, DMSO-d6) δ 12.33 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.27 (d, J = 5.0 Hz, 1H), 7.97-7.72 (m, 2H), 6.97 (s, 1H), 4.33 (s, 3H), 2.94 (s, 6H).
1-2049
1-2050
1-2051	SMe			1H NMR (500 MHz, DMSO-d6) δ 12.23 (s, 1H), 8.59 (d, J = 5.0 Hz, 1H), 7.84-7.78 (m, 2H), 7.51-7.42 (m, 3H), 4.37 (s, 3H), 2.48 (s, 3H).
1-2052	SMe			1H NMR (500 MHz, DMSO-d6) δ 12.26 (s, 1H), 8.56 (d, J = 5.0 Hz, 1H), 8.11-8.04 (m, 2H), 7.77-7.71 (m, 2H), 7.66 (d, J = 5.0 Hz, 1H), 4.36 (s, 3H), 2.22 (s, 3H).
1-2053	SMe			1H NMR (500 MHz, DMSO-d6) δ 12.29 (s, 1H), 8.62 (d, J = 5.0 Hz, 1H), 7.89-7.83 (m, 2H), 7.72-7.66 (m, 2H), 7.52 (d, J = 5.0 Hz, 1H), 6.99 (s, 2H), 4.33 (s, 3H), 2.22 (s, 3H).
1-2054	SMe			1H NMR (500 MHz, DMSO-d6) δ 12.24 (s, 1H), 8.79 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.93 (d, J = 8.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 4.34 (s, 3H), 2.53 (s, 3H).
1-2055	SMe			1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.62 (s, 1H), 8.31 (d, J = 8.0 Hz, 1H), 8.22 (d, J = 6.0 Hz, 1H), 7.59 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H), 2.54 (s, 3H).
1-2056	SMe
1-2057	SMe			1H NMR (500 MHz, DMSO-d6) δ 12.23 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 7.83 (t, J = 57.0 Hz, 1H), 7.70 (s, 1H), 7.58 (d, J = 5.0 Hz, 1H), 6.96 (s, 1H), 4.34 (s, 3H), 2.59 (s, 3H).
1-2058		CH3		1H NMR (500 MHz, DMSO-d6) δ 12.23 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.57 (d, J = 5.0 Hz, 1H), 4.37 (s, 3H), 2.72 (s, 3H), 2.61 (s, 3H).
1-2059				1H NMR (500 MHz, DMSO-d6) δ 12.26 (s, 1H), 8.99 (d, J = 5.0 Hz, 1H), 7.88 (d, J = 5.0 Hz, 1H), 6.99 (dd, J = 17.0, 10.0 Hz, 1H), 6.10 (dd, J = 14.0, 10.0 Hz, 1H), 5.72 (dd, J = 17.0, 14.0 Hz, 1H), 4.31 (s, 3H), 2.66 (s, 3H).
1-2060				1H NMR (500 MHz, DMSO-d6) δ 12.28 (s, 1H), 9.09 (d, J = 5.0 Hz, 1H), 7.94 (s, 1H), 7.82 (d, J = 5.0 Hz, 1H), 6.92 (s, 1H), 4.36 (s, 3H), 3.92 (s, 3H), 2.71 (s, 3H).
1-2061	Cl	OMe		1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.70 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.60 (s, 3H).
1-2062	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.24 (s, 1H), 8.06 (d, J = 5.0 Hz, 1H), 7.22 (d, J = 5.0 Hz, 1H), 4.39 (s, 2H), 4.30 (s, 3H).
1-2063	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.22 (s, 1H), 8.17 (d, J = 5.0 Hz, 1H), 7.47-7.39 (m, 2H), 7.32 (d, J = 5.0 Hz, 1H), 7.18-7.11 (m, 2H), 7.00-6.96 (m, 1H), 4.35 (s, 3H).
1-2064	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.22 (s, 1H), 8.08 (d, J = 5.0 Hz, 1H), 7.43-7.27 (m, 5H), 7.22 (d, J = 5.0 Hz, 1H), 5.33 (s, 2H), 4.40 (s, 3H).
1-2065	Cl	SMe		1H NMR (500 MHz, DMSO-d6) δ 12.20 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.70 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 2.60 (s, 3H).
1-2066	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.24 (s, 1H), 8.36 (d, J = 5.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H), 2.10 (t, J = 5.0 Hz, 2H), 1.68-1.64 (m, 2H), 1.02 (t, J = 8.0 Hz, 3H).
1-2067	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.47 (d, J = 5.0 Hz, 1H), 7.69 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H), 1.35 (s, 9H).
1-2068	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.23 (s, 1H), 8.39 (d, J = 5.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 7.36-7.30 (m, 3H), 7.28-7.21 (m, 2H), 4.55 (s, 2H), 4.33 (s, 3H).
1-2069	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.23 (s, 1H), 8.48 (d, J = 5.0 Hz, 1H), 7.66 (d, J = 5.0 Hz, 1H), 7.17 (d, J = 7.0 Hz, 2H), 7.12-7.06 (m, 2H), 4.53 (s, 2H), 4.39 (s, 3H), 3.51 (s, 3H).
1-2070	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.28 (s, 1H), 8.84 (d, J = 5.0 Hz, 1H), 8.00 (d, J = 5.0 Hz, 1H), 4.30 (s, 3H), 2.83 (t, J = 5.0 Hz, 1H), 2.55 (t, J = 5.0 Hz, 1H), 1.47-1.42 (m, 2H), 0.93 (t, J = 8.0 Hz, 3H).
1-2071	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.29 (s, 1H), 8.96 (d, J = 5.0 Hz, 1H), 8.16 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.13 (t, J = 8.0 Hz, 2H), 1.56- 1.48 (m, 2H), 0.90 (t, J = 8.0 Hz, 3H).
1-2072	Cl	NH2		1H NMR (500 MHz, DMSO-d6) δ 12.31 (s, 1H), 8.39 (d, J = 5.0 Hz, 1H), 7.45 (d, J = 5.0 Hz, 1H), 6.30 (s, 2H), 4.33 (s, 3H).
1-2073	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.27 (s, 1H), 9.25 (s, 1H), 8.42 (d, J = 5.0 Hz, 1H), 7.44 (d, J = 5.0 Hz, 1H), 4.37 (s, 3H), 3.04 (s, 3H).
1-2074	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.27 (s, 1H), 8.34 (d, J = 5.0 Hz, 1H), 7.40 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.19 (s, 6H).
1-2075	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.31 (s, 1H), 10.22 (s, 1H), 8.41 (d, J = 5.0 Hz, 1H), 7.78- 7.72 (m, 2H), 7.42 (d, J = 5.0 Hz, 1H), 7.33-7.28 (m, 2H), 7.02-6.99 (m, 1H), 4.33 (s, 3H).
1-2076	Cl			1H NMR (500 MHz, DMSO-d6) δ 12.23 (s, 1H), 8.99 (s, 1H), 8.37 (d, J = 5.0 Hz, 1H), 7.35 (d, J = 5.0 Hz, 1H), 7.21-7.15 (m, 2H), 6.92-6.86 (m, 2H), 4.62 (s, 2H), 4.30 (s, 3H), 3.79 (s, 3H).
1-2077	F	OMe		1H NMR (500 MHz, DMSO-d6) δ 12.28 (s, 1H), 8.45 (d, J = 5.0 Hz, 1H), 7.83 (d, J = 5.0 Hz, 1H), 4.30 (s, 3H), 3.55 (s, 3H).
1-2078	F			1H NMR (500 MHz, DMSO-d6) δ 12.28 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 8.15 (dd, J = 8.0, 5.0 Hz, 1H), 4.33 (s, 3H), 2.81 (t, J = 5.0 Hz, 1H), 2.54 (t, J = 5.0 Hz, 1H), 1.47-1.41 (m, 2H), 0.92 (t, J = 8.0 Hz, 3H).
1-2079	OMe	OMe		1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.59 (d, J = 5.0 Hz, 1H), 7.38 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H), 3.62 (s, 3H), 3.45 (s, 3H).
1-2080	OMe			1H NMR (500 MHz, DMSO-d6) δ 12.29 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.39 (s, 3H), 2.81 (t, J = 5.0 Hz, 1H), 2.54 (t, J = 5.0 Hz, 1H), 1.47-1.41 (m, 2H), 0.93 (t, J = 8.0 Hz, 3H).
1-2081	OMe	NH2		1H NMR (500 MHz, DMSO-d6) δ 12.27 (s, 1H), 8.23 (d, J = 5.0 Hz, 1H), 7.61 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 4.21 (s, 2H), 3.81 (s, 3H).
1-2082	SMe	OMe		1H NMR (500 MHz, DMSO-d6) δ 12.24 (s, 1H), 8.02 (d, J = 5.0 Hz, 1H), 7.28 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.92 (s, 3H), 2.31 (s, 3H).
1-2083	SMe	SMe		1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.59 (d, J = 5.0 Hz, 1H), 7.38 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H), 2.62 (s, 3H), 2.20 (s, 3H).
1-2084	SMe			1H NMR (500 MHz, DMSO-d6) δ 12.33 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 2.85 (t, J = 5.0 Hz, 1H), 2.55 (t, J = 5.0 Hz, 1H), 2.39 (s, 3H), 1.46-1.40 (m, 2H), 0.92 (t, J = 8.0 Hz, 3H).
1-2085		OMe		1H NMR (500 MHz, DMSO-d6) δ 12.29 (s, 1H), 8.28 (d, J = 5.0 Hz, 1H), 7.14 (d, J = 5.0 Hz, 1H), 4.35 (s, 3H), 3.92 (s, 3H), 2.86 (s, 3H).
1-2086		OMe		1H NMR (500 MHz, DMSO-d6) δ 12.23 (s, 1H), 8.45 (d, J = 5.0 Hz, 1H), 7.34 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.95 (s, 3H), 3.24 (s, 3H).
1-2087	NH2			1H NMR (500 MHz, DMSO-d6) δ 12.20 (s, 1H), 8.45 (d, J = 5.0 Hz, 1H), 7.80 (d, J = 5.0 Hz, 1H), 5.83 (s, 2H), 4.33 (s, 3H), 2.76 (t, J = 8.0 Hz, 1H), 2.53 (t, J = 8.0 Hz, 1H), 1.47-1.42 (m, 2H), 0.88 (t, J = 8.0 Hz, 3H).
1-2088				1H NMR (500 MHz, DMSO-d6) δ 12.21 (s, 1H), 7.98 (d, J = 5.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 6.58 (s, 1H), 5.95 (s, 1H), 4.30 (s, 3H), 2.73 (s, 3H), 2.68 (s, 3H).
1-2089		OMe		1H NMR (500 MHz, DMSO-d6) δ 12.35 (s, 1H), 7.87 (d, J = 5.0 Hz, 1H), 7.57 (d, J = 5.0 Hz, 1H), 4.30 (s, 3H), 3.83 (s, 3H), 2.91 (s, 6H).
1-2090				1H NMR (500 MHz, DMSO-d6) δ 12.26 (s, 1H), 8.58 (d, J = 5.0 Hz, 1H), 8.28 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 2.93 (s, 6H), 2.82 (t, J = 5.0 Hz, 1H), 2.54 (t, J = 5.0 Hz, 1H), 1.47-1.41 (m, 2H), 0.92 (t, J = 7.9 Hz, 3H).
1-2091				1H NMR (500 MHz, DMSO-d6) δ 12.33 (s, 1H), 8.09 (d, J = 5.0 Hz, 1H), 7.19 (d, J = 5.0 Hz, 1H), 6.50 (s, 1H), 4.36 (s, 3H), 2.81 (s, 6H), 2.73 (s, 3H).
1-2092				1H NMR (500 MHz, DMSO-d6) δ 12.28 (s, 1H), 8.19 (d, J = 5.0 Hz, 1H), 7.80 (d, J = 5.0 Hz, 1H), 4.36 (s, 3H), 3.18 (s, 6H), 2.93 (s, 6H).
1-2093				1H NMR (500 MHz, DMSO-d6) δ 12.31 (s, 1H), 8.62 (d, J = 5.0 Hz, 1H), 7.87 (d, J = 5.0 Hz, 1H), 7.38-7.32 (m, 2H), 6.92-6.86 (m, 2H), 6.22 (s, 1H), 4.34-4.31 (m, 5H), 3.79 (s, 3H), 2.75 (t, J = 5.0 Hz, 1H), 2.55 (t, J = 5.0 Hz, 1H), 1.50-1.44 (m, 2H), 0.95 (t, J = 8.0 Hz, 3H).
1-2094		OMe		1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.55 (d, J = 5.0 Hz, 1H), 6.69-6.64 (m, 1H), 5.74-5.70 (m, 1H), 5.46-5.42 (m, 1H), 4.33 (s, 3H), 3.63 (s, 3H).
1-2095		OMe		1H NMR (500 MHz, DMSO-d6) δ 12.31 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.56 (d, J = 5.0 Hz, 1H), 7.23-7.13 (m, 4H), 4.33 (s, 3H), 3.80 (s, 3H).
1-2096
1-2097				1H NMR (500 MHz, DMSO-d6) δ 12.22 (s, 1H), 8.60 (d, J = 5.0 Hz, 1H), 8.23 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 2.85 (t, J = 8.0 Hz, 1H), 2.65 (t, J = 8.0 Hz, 1H), 2.48 (s, 3H), 2.40 (s, 3H) 1.47-1.41 (m, 2H), 0.91 (t, J = 8.0 Hz, 3H).

The method for preparing the compound of the invention will be explained in detail in the following program and embodiment. The material is commercial available or prepared through known method reported in the literature or shown in the route. Those skilled in the art should understand that the compound of the invention can also be synthesized by other synthetic route. Although the detailed material and reaction condition in the synthetic route have been explicated in the following text, it is still easy to be replaced by other similar material and condition. Isomer of the compound, for example, that produced with the variation of the preparation method of the present invention is included in the scope of the present invention. In addition, the following preparation method can be further modified according to the disclosures of the present invention by using common chemical method known to those skilled in the art, for example, protection of suitable group in the process of the reaction, etc.

The following method of application can be used to improve further understanding of the preparation method of the present invention. The specific material, class and condition have been determined to be further explication of the present invention, not to be any limit of the reasonable scope thereof. Reagents of the following synthetic compound showed in the table can either be purchased from the market or easily prepared by those skilled in the art.

Examples of representative compounds are as follows, the synthetic methods of other compounds are similar, and will not be described in detail here.

1. Synthesis of Compound 1-1

(1) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound a, 3.0 equivalents of sodium hydroxide, and 1.2 equivalents of 1-1-1 were charged sequentially at room temperature. After dissolved with 10:1 dioxane-water (10V), nitrogen replacement was performed three times under stirring, the catalyst 1,1′-bis(diphenylphosphino)ferrocene dichloride palladium(II) dichloromethane complex (1%) was added, nitrogen replacement was performed three times, then heated to 120° C., and reacted at this temperature for 16-24 hours. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added, the insolubles were removed by filtration, and the mother liquor was adjusted to pH 1-2 with 2M hydrochloric acid solution, then extracted three times with ethyl acetate (5V). The organic phases were combined and distilled under reduced pressure to remove ethyl acetate. The product 1-1-2 was obtained by reverse-phase purification with yield of 78%.

(2) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound 1-1-2 was charged at room temperature. After dissolved with dichloromethane (10V), 1.1 equivalent of N,N′-carbonyldiimidazole (CDI) was added, and reacted at 30-40° C. for 1 hour under stirring. After stirring, 1.2 equivalent of b and 1.0 equivalent of 1,8-diazabicycloundec-7-ene (DBU) were added, and continued to react at 30-40° C. for 16-24 hours under stirring. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added to the reaction system, stirred, extracted, and the organic phase was poured into the waste liquid. The water phase was adjusted to pH 5-6 with 2M hydrochloric acid solution, and a large amount of solid was precipitated out at this time. After stirring for 15-30 minutes, the solid was filtered to obtain the product, and the product was dried to remove water with yield of about 72%.

2. Synthesis of Compound 1-17

It can be prepared by referring to the above method for preparing compound 1-1; or it can be prepared by the following method:

(1) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound a was charged at room temperature. After dissolved with dichloromethane (10V), 1.1 equivalent of N,N′-carbonyldiimidazole (CDI) was added, and reacted at 30-40° C. for 1 hour under stirring. After stirring, 1.2 equivalent of b and 1.0 equivalent of 1,8-diazabicycloundec-7-ene (DBU) were added, and continued to react at 30-40° C. for 16-24 hours under stirring. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added to the reaction system, stirred, extracted, and the organic phase was poured into the waste liquid. The water phase was adjusted to pH 5-6 with 2M hydrochloric acid solution, and a large amount of solid was precipitated out at this time. After stirring for 15-30 minutes, the solid was filtered to obtain the product, and the product was dried to remove water with yield of about 75%,

(2) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound 1-17-1, 3.0 equivalents of potassium carbonate, and 1.2 equivalents of c were charged sequentially at room temperature. After dissolved with 10:1 dioxane-water (10V), nitrogen replacement was performed three times under stirring, the catalyst 1,1′-bis(diphenylphosphino)ferrocene dichloride palladium(II) dichloromethane complex (1%) was added, nitrogen replacement was performed three times, then heated to 110° C., and reacted at this temperature for 16-24 hours. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added, the insolubles were removed by filtration, and the mother liquor was adjusted to pH 5-6 with 2M hydrochloric acid solution, then extracted three times with ethyl acetate (5V). The organic phases were combined and distilled under reduced pressure to remove ethyl acetate. The product was obtained by reverse-phase purification with yield of 50%.

3. Synthesis of Compounds 1-203 and 1-205

(1) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound 1-203-1 (It can be prepared by referring to the above method for preparing compound 1-17) was charged at room temperature. After dissolved with N,N-dimethylformamide (10V), 1.0 equivalent of sodium thiomethoxide aqueous solution (20% content) was added, and reacted at 50-60° C. for 6-8 hours under stirring. The reaction solution was sampled and when the remaining raw materials were less than 2% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added, and adjusted to pH 5-6 with 2M hydrochloric acid solution, and the solid was precipitated out at this time, the insolubles were removed by filtration. The mother liquor was distilled under reduced pressure to remove the solvent, and the compound 1-203 was obtained by reverse-phase purification with yield of about 62%.

(2) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound 1-203 was charged at room temperature. After dissolved with dichloromethane (10V), 1.0 equivalent of 1-205-1 (85% content) was added, and reacted at 10-20° C. for 15-30 minutes under stirring. The reaction solution was sampled and when the remaining raw materials were less than 1% according to LC-MS detection, the reaction was terminated. After the reaction was completed, sodium thiosulfate aqueous solution was added to quench the reaction, the insolubles were removed by filtration, distilled under reduced pressure to remove the solvent, and the compound 1-205 was obtained by reverse-phase purification with yield of about 50%.

Or

can be prepared from

by referring to the above preparation method, then

can be prepared, and reacts with

respectively to obtain compound 1-203 and compound 1-205 by referring to the synthesis step (2) of the above compound 1-1.

4. Synthesis of Compound 1-223

(1) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound a, 3.0 equivalents of sodium hydroxide, and 2.5 equivalents of c were charged sequentially at room temperature. After dissolved with 10:1 dioxane-water (10V), nitrogen replacement was performed three times under stirring, the catalyst 1,1′-bis(diphenylphosphino)ferrocene dichloride palladium(II) dichloromethane complex (1%) was added, nitrogen replacement was performed three times, then heated to 120° C., and reacted at this temperature for 16-24 hours. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added, the insolubles were removed by filtration, and the mother liquor was adjusted to pH 1-2 with 2M hydrochloric acid solution, then extracted three times with ethyl acetate (5V). The organic phases were combined and distilled under reduced pressure to remove ethyl acetate. The product 1-223-1 was obtained by reverse-phase purification with yield of 45%.

(2) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound 1-223-1 was charged at 10-20° C. After dissolved with pyridine (10V), 10% 4-dimethylaminopyridine (DMAP) and 1.2 equivalents of compound b were charged sequentially, and 3.0 equivalents of thionyl chloride was added in a dropwise manner at 10-20° C. under stirring, then heated to 30-40° C., and reacted for 2 hours under stirring. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, the pyridine was removed by distillation under reduced pressure, dissolved with 10V water, adjusted to pH 2-3 with 1M hydrochloric acid, then extracted three times with dichloromethane (5V). The organic phases were combined and distilled under reduced pressure to remove the solvent. The product 1-223 was obtained by reverse-phase purification with yield of about 52%.

5. Synthesis of Compound 1-249

It can be prepared by referring to the above method for preparing compound 1-1; or it can be prepared by the following method:

To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound 1-17-1, 3.0 equivalents of potassium carbonate, and 1.2 equivalents of 1-249-1 were charged sequentially at room temperature. After dissolved with 10:1 dioxane-water (10V), nitrogen replacement was performed three times under stirring, the catalyst 1,1′-bis(diphenylphosphino)ferrocene dichloride palladium(II) dichloromethane complex (1%) was added, nitrogen replacement was performed three times, then heated to 110° C., and reacted at this temperature for 16-24 hours. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added, the insolubles were removed by filtration, and the mother liquor was adjusted to pH 5-6 with 2M hydrochloric acid solution, then extracted three times with ethyl acetate (5V). The organic phases were combined and distilled under reduced pressure to remove ethyl acetate. The product was obtained by reverse-phase purification with yield of 50%.

6. Synthesis of Compound 1-962

(1) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound a, 3.0 equivalents of potassium carbonate, and 1.1 equivalents of c were charged sequentially at room temperature. After dissolved with 10:1 dioxane-water (10V), nitrogen replacement was performed three times under stirring, the catalyst 1,1′-bis(diphenylphosphino)ferrocene dichloride palladium(II) dichloromethane complex (1%) was added, nitrogen replacement was performed three times, then heated to 120° C., and reacted at this temperature for 16-24 hours. The reaction solution was sampled and when the remaining raw materials were less than 1% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added, the insolubles were removed by filtration, extracted two times with ethyl acetate (5V), and the water phases were adjusted to pH 2-3 with 2M hydrochloric acid solution, then the solid was precipitated out, filtered and dried to obtain the product 1-962-1 with yield of 82%.

(2) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound 1-962-1 was charged at room temperature. After dissolved with dichloromethane (10V), 1.1 equivalent of N,N′-carbonyldiimidazole (CDI) was added, and reacted at 30-40° C. for 1 hour under stirring. After stirring, 1.2 equivalent of d and 1.0 equivalent of 1,8-diazabicycloundec-7-ene (DBU) were added, and continued to react at 30-40° C. for 5-8 hours under stirring. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added to the reaction system, stirred, extracted, and the organic phase was poured into the waste liquid. The water phase was adjusted to pH 5-6 with 2M hydrochloric acid solution, and a large amount of solid was precipitated out at this time. After stirring for 15-30 minutes, the solid was filtered to obtain the product, and the product was dried to remove water with yield of about 69%.

Biological Activity Evaluation:

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

Level 5: growth control rate is above 85%;

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

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

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

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

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

The above growth control rates are fresh weight control rates.

Experiment on weeding effect in post-emergence stage: monocotyledonous and dicotyledonous weed seeds and major crop seeds (wheat, corn, rice, soybean, cotton, oilseed rape, millet, sorghum) were placed in plastic pots filled with soil, then covered with 0.5-2 cm of soil, allowed to grow in a good greenhouse environment. After 2 weeks of sowing, the test plants were treated in the 2-3 leaf stage. The tested compounds of the present invention were respectively dissolved in acetone at the dosage of 2000, 1000, 500, 250, 125 g/ha, then added with Tween 80 and 1.5 liter/ha of emulsifiable concentrate of methyl oleate as synergist, diluted with a certain amount of water to obtain a solution with a certain concentration, and sprayed with a spray tower onto the plants. After the application, the plants were cultured for 3 weeks in the greenhouse, and then the experimental results were listed in Table 1.

TABLE 1
Results on weeding effect in post-emergence stage
Com-	Descurainia	Abutilon	Amaranthus	Chenopodium
pound No.	sophia	theophrasti	retroflexus L.	album
1-1	5	5	5	5
1-2	5	5	5	5
1-3	5	5	5	5
1-4	5	5	5	5
1-5	5	5	5	5
1-6	5	5	5	5
1-7	5	5	5	5
1-8	5	5	5	5
1-9	5	5	5	5
1-10	5	5	5	5
1-11	5	5	5	5
1-12	5	5	5	5
1-13	5	5	5	5
1-14	5	5	5	5
1-15	5	5	5	5
1-16	5	5	5	5
1-17	5	5	5	5
1-18	5	5	5	5
1-19	5	5	5	5
1-20	5	5	5	5
1-21	5	5	5	5
1-22	5	5	5	5
1-23	5	5	5	5
1-24	5	5	5	5
1-25	5	5	5	5
1-26	5	5	5	5
1-27	5	5	5	5
1-28	5	5	5	5
1-29	5	5	5	5
1-30	5	5	5	5
1-31	5	5	5	5
1-32	5	5	5	5
1-33	5	5	5	5
1-34	5	5	5	5
1-35	5	5	5	5
1-36	5	5	5	5
1-37	5	5	5	5
1-38	5	5	5	5
1-39	5	5	5	5
1-40	5	5	5	5
1-41	5	5	5	5
1-42	5	5	5	5
1-43	5	5	5	5
1-44	5	5	5	5
1-45	5	5	5	5
1-46	5	5	5	5
1-47	5	5	5	5
1-48	5	5	5	5
1-49	5	5	5	5
1-50	5	5	5	5
1-51	5	5	5	5
1-52	5	5	5	5
1-53	5	5	5	5
1-54	5	5	5	5
1-55	5	5	5	5
1-56	5	5	5	5
1-57	5	5	5	5
1-58	5	5	5	5
1-59	5	5	5	5
1-60	5	5	5	5
1-61	5	5	5	5
1-62	5	5	5	5
1-63	5	5	5	5
1-64	5	5	5	5
1-65	5	5	5	5
1-66	5	5	5	5
1-67	5	5	5	5
1-68	5	5	5	5
1-69	5	5	5	5
1-70	5	5	5	5
1-71	5	5	5	5
1-72	5	5	5	5
1-73	5	5	5	5
1-74	5	5	5	5
1-75	5	5	5	5
1-76	5	5	5	5
1-77	5	5	5	5
1-78	5	5	5	5
1-79	5	5	5	5
1-80	5	5	5	5
1-81	5	5	5	5
1-82	5	5	5	5
1-83	5	5	5	5
1-84	5	5	5	5
1-85	5	5	5	5
1-86	5	5	5	5
1-87	5	5	5	5
1-88	5	5	5	5
1-89	5	5	5	5
1-90	5	5	5	5
1-91	5	5	5	5
1-92	5	5	5	5
1-93	5	5	5	5
1-94	5	5	5	5
1-95	5	5	5	5
1-96	5	5	5	5
1-97	5	5	5	5
1-98	5	5	5	5
1-99	5	5	5	5
1-100	5	5	5	5
1-101	5	5	5	5
1-102	5	5	5	5
1-103	5	5	5	5
1-104	5	5	5	5
1-105	5	5	5	5
1-106	5	5	5	5
1-107	5	5	5	5
1-108	5	5	5	5
1-109	5	5	5	5
1-110	5	5	5	5
1-111	5	5	5	5
1-112	5	5	5	5
1-113	5	5	5	5
1-114	5	5	5	5
1-115	5	5	5	5
1-116	5	5	5	5
1-117	5	5	5	5
1-118	5	5	5	5
1-119	5	5	5	5
1-120	5	5	5	5
1-121	5	5	5	5
1-122	5	5	5	5
1-123	5	5	5	5
1-124	5	5	5	5
1-125	5	5	5	5
1-126	5	5	5	5
1-127	5	5	5	5
1-128	5	5	5	5
1-129	5	5	5	5
1-130	5	5	5	5
1-131	5	5	5	5
1-132	5	5	5	5
1-133	5	5	5	5
1-134	5	5	5	5
1-135	5	5	5	5
1-136	5	5	5	5
1-137	5	5	5	5
1-138	5	5	5	5
1-139	5	5	5	5
1-140	5	5	5	5
1-141	5	5	5	5
1-142	5	5	5	5
1-143	5	5	5	5
1-144	5	5	5	5
1-145	5	5	5	5
1-146	5	5	5	5
1-147	5	5	5	5
1-148	5	5	5	5
1-149	5	5	5	5
1-150	5	5	5	5
1-151	5	5	5	5
1-152	5	5	5	5
1-153	5	5	5	5
1-154	5	5	5	5
1-155	5	5	5	5
1-156	5	5	5	5
1-157	5	5	5	5
1-158	5	5	5	5
1-159	5	5	5	5
1-160	5	5	5	5
1-161	5	5	5	5
1-162	5	5	5	5
1-163	5	5	5	5
1-164	5	5	5	5
1-165	5	5	5	5
1-166	5	5	5	5
1-167	5	5	5	5
1-168	5	5	5	5
1-169	5	5	5	5
1-170	5	5	5	5
1-171	5	5	5	5
1-172	5	5	5	5
1-173	5	5	5	5
1-174	5	5	5	5
1-175	5	5	5	5
1-176	5	5	5	5
1-177	5	5	5	5
1-178	5	5	5	5
1-179	5	5	5	5
1-180	5	5	5	5
1-181	5	5	5	5
1-182	5	5	5	5
1-183	5	5	5	5
1-184	5	5	5	5
1-185	5	5	5	5
1-186	5	5	5	5
1-187	5	5	5	5
1-188	5	5	5	5
1-189	5	5	5	5
1-190	5	5	5	5
1-191	5	5	5	5
1-192	5	5	5	5
1-193	5	5	5	5
1-194	5	5	5	5
1-195	5	5	5	5
1-196	5	5	5	5
1-197	5	5	5	5
1-198	5	5	5	5
1-199	5	5	5	5
1-200	5	5	5	5
1-201	5	5	5	5
1-202	5	5	5	5
1-203	5	5	5	5
1-204	5	5	5	5
1-205	5	5	5	5
1-206	5	5	5	5
1-207	5	5	5	5
1-208	5	5	5	5
1-209	5	5	5	5
1-210	5	5	5	5
1-211	5	5	5	5
1-212	5	5	5	5
1-213	5	5	5	5
1-214	5	5	5	5
1-215	5	5	5	5
1-216	5	5	5	5
1-217	5	5	5	5
1-218	5	5	5	5
1-219	5	5	5	5
1-220	5	5	5	5
1-221	5	5	5	5
1-222	5	5	5	5
1-223	5	5	5	5
1-228	5	5	5	5
1-229	5	5	5	5
1-230	5	5	5	5
1-233	5	5	5	5
1-234	5	5	5	5
1-249	5	5	5	5
1-307	5	5	5	5
1-334	5	5	5	5
1-650	5	5	5	5
1-962	5	5	5	5
1-1257	5	5	5	5
1-1286	5	5	5	5
1-1577	5	5	5	5
1-1607	5	5	5	5
1-1918	5	5	5	5
1-1925	5	5	5	5
1-1972	5	5	5	5
1-2004	5	5	5	5
1-2006	5	5	5	5
1-2010	5	5	5	5
1-2016	5	5	5	5
1-2029	5	5	5	5
1-2044	5	5	5	5
1-2052	5	5	5	5
1-2053	5	5	5	5
1-2061	5	5	5	5
1-2062	5	5	5	5
1-2063	5	5	5	5
1-2064	5	5	5	5
1-2065	5	5	5	5
1-2069	5	5	5	5
1-2070	5	5	5	5
1-2071	5	5	5	5
1-2075	5	5	5	5
Note:
The application dose was active ingredient 2000 g/ha.

In addition, under the active ingredient of 250 g/ha, many compounds also show good crop selectivity and excellent control effect on key weeds. For example, see Table 2:

TABLE 2
Test results
	Alopecurus	Beckmannia	Alopecurus	Sclerochloa	Descurainia
No.	aequalis	syzigachne	myosuroides	dura	sophia	Wheat
1-15	5	5	5	5	5	0
1-17	5	5	5	5	5	0
Control	0	0	0	0	0	0
compound A

Control Compound A:

Experiment on Weed Effect in Pre-Emergence Stage

Seeds of monocotyledonous and dicotyledonous weeds and main crops (e.g. wheat, corn, rice, soybean, cotton, oilseed rape, millet and sorghum) were put into a plastic pot loaded with soil and covered with 0.5-2 cm soil. The test compounds of the present invention was dissolved with acetone, then added with tween 80, diluted by a certain amount of water to reach a certain concentration, and sprayed immediately after sowing. The obtained seeds were incubated for 4 weeks in the greenhouse after spraying and the test results were observed. It was observed that the herbicide mostly had excellent effect at the application rate of 2000 g a.i./ha, especially to weeds such as Echinochloa crusgalli, Digitaria sanguinalis, Abutilon theophrasti, etc. And many compounds had good selectivity for corn, wheat, rice, soybean, oilseed rape, etc.

It is indicated from the experiment that the compounds of the present invention generally have good weed control efficacy, especially for the major cyperaceae weeds like Echinochloa crusgalli, Digitaria sanguinalis, and Setaria viridis, etc., and the major broad-leaved weeds like Abutilon theophrasti, Rorippa indica, and Bidens pilosa L., etc., which are widely occurring in corn, rice, and wheat fields, and have excellent commercial value. Above all, it is noted that they have extremely high activity to weeds, which are resistant to ALS inhibitor, like Rorippa indica, Descurainia sophia, Capsella bursa-pastoris, Lithospermum arvense, Galium aparine L., Stellaria media, Setaria viridis, Echinochloa crusgalli, Digitaria sanguinalis, Alopecurus aequalis, Beckmannia syzigachne, etc.

Transplanted rice safety evaluation and weed control effect evaluation in rice field:

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

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.

The fertility condition of Echinochloa crusgalli, Scirpus juncoides, Bidens tripartita L., Sagittaria trifolia and Monochoria vaginalis 14 days after the treatment of the compound of the invention and the fertility condition of rice 21 days after the treatment of the compound of the invention respectively with the naked eye. Evaluate the weed control effect with the above 0-5 activity standard level, many compounds show excellent activity and selectivity. Wherein, the seeds of Echinochloa crusgali, Scirpus juncoides, Bidens tripartita, Sagittaria trifolia and Monochoria vaginalis were collected from Heilongjiang Province of China. The tests indicated that the weeds were resistant to the common doses of Pyrazosulfuron-ethyl and Penoxsulam.

It could be seen from this experiment that the compound of the present invention has excellent activity against the anti-ALS weeds which is a serious challenge in the production, and could solve the increasingly serious problem of resistance.

At the same time, it is found after several tests that the compound of the present invention and its composition have good selectivity to many gramineae grass such as Zoysia japonica, bermuda grass, tall fescue, bluegrass, ryegrass and seashore paspalum etc, and is able to control many important grass weeds and broadleaf 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.

Claims

1. A 4-pyridinyl formamide compound or derivative thereof, as shown in Formula I:

2. The 4-pyridinyl formamide compound or derivative thereof according to claim 1, which is characterized in that, X, and Y each independently represent nitro, halogen, cyano, formyl, thiocyano, mercapto; C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkyl-C1-C6 alkyl, or C3-C8 cycloalkenyl-C1-C6 alkyl, which is with or without halogen; OR1, COR1, COOR1, OCOR1, OCOOR1, NR3SO2R2, OSO2R2, S(O)mR2, NR3COR1, NR3COOR1, C(O)NR3OR1, SO2OR1, C(O)NR4R5, NR3C(O)NR4R5, OC(O)NR4R5, SO2NR4R5, C(S)R1, C(S)OR1, C(S)SR2, C(O)SR2, SC(O)R1, SC(S)R1, OC(S)R1, —(C1-C6)alkyl-C(S)R1, —(C1-C6)alkyl-C(S)OR1, —(C1-C6)alkyl-C(O)SR1, —(C1-C6)alkyl-C(S)SR1, —(C1-C6)alkyl-SC(O)R1, —(C1-C6)alkyl-OC(S)R1, —(C1-C6)alkyl-SC(S)R1, —O—(C1-C6)alkyl-NR4R5, —S—(C1-C6)alkyl-NR4R5, —(C1-C6)alkyl-O—(C1-C6)alkyl-NR4R5, —(C1-C6)alkyl-S—(C1-C6)alkyl-NR4R5, —(C1-C6)alkyl-(C═S)n—NR4R5, —NH—(C1-C6)alkyl-NR4R5, —(C1-C6)alkyl-OR1, —(C1-C6)alkyl-COR1, —(C1-C6)alkyl-CO2R1, —(C1-C6)alkyl-OCOR1, —(C1-C6)alkyl-NR3COR1, —(C1-C6)alkyl-SO2OR1, —(C1-C6)alkyl-NR3SO2R2, —(C1-C6)alkyl-OSO2R2, -alkyl-S(O)mR2, —(C1-C6)alkyl-CONR4R5, —(C1-C6)alkyl-SO2NR4R5, NR4R5,

3. The 4-pyridinyl formamide compound or derivative thereof according to claim 1, which is characterized in that, X represents nitro, halogen, cyano, formyl, thiocyano, mercapto; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkyl-C1-C3 alkyl, or C3-C6 cycloalkenyl-C1-C3 alkyl, which is with or without halogen; OR1, COR1, COOR1, OCOR1, OCOOR1, NR3SO2R2, OSO2R2, S(O)mR2, NR3COR1, NR3COOR1, C(O)NR3OR1, SO2OR1, C(O)NR4R5, NR3C(O)NR4R5, OC(O)NR4R5, SO2NR4R5, C(S)R1, C(S)OR1, C(S)SR2, C(O)SR2, SC(O)R1, SC(S)R1, OC(S)R1, —(C1-C3)alkyl-C(S)R1, —(C1-C3)alkyl-C(S)OR1, —(C1-C3)alkyl-C(O)SR1, —(C1-C3)alkyl-C(S)SR1, —(C1-C3)alkyl-SC(O)R1, —(C1-C3)alkyl-OC(S)R1, —(C1-C3)alkyl-SC(S)R1, —O—(C1-C3)alkyl-NR4R5, —S—(C1-C3)alkyl-NR4R5, —(C1-C3)alkyl-O—(C1-C3)alkyl-NR4R5, —(C1-C3)alkyl-S—(C1-C3)alkyl-NR4R5, —(C1-C3)alkyl-(C═S)n—NR4R5, —NH—(C1-C3)alkyl-NR4R5, —(C1-C3)alkyl-OR1, —(C1-C3)alkyl-COR1, —(C1-C3)alkyl-CO2R1, —(C1-C3)alkyl-OCOR1, —(C1-C3)alkyl-NR3COR1, —(C1-C3)alkyl-SO2OR1, —(C1-C3)alkyl-NR3SO2R2, —(C1-C3)alkyl-OSO2R2, -alkyl-S(O)mR2, —(C1-C3)alkyl-CONR4R5, —(C1-C3)alkyl-SO2NR4R5, NR4R5,

4. The 4-pyridinyl formamide compound or derivative thereof according to claim 1, which is characterized in that, X represents halogen, nitro, cyano, OR1, S(O)mR2, NR3COR1, NR4R5,

5. The 4-pyridinyl formamide compound or derivative thereof according to claim 1, which is characterized in that, X represents chlorine, fluorine, bromine, methyl, ethyl, isopropyl, vinyl, allyl, ethynyl, cyclopropyl, trifluoromethyl,

6.-10. (canceled)

11. The 4-pyridinyl formamide compound or derivative thereof according to claim 1, which is selected from the compounds of formula I as listed in Table A1.

12. A method for preparing the 4-pyridinyl formamide compound of claim 1, comprising subjecting the compound of formula II and the compound of formula III to an amidation reaction to obtain the compound of formula I as follows:

13. The method of claim 12, wherein the reaction is carried out in the presence of SOCl2 as the halogenating agent, 4-dimethylaminopyridine as the catalyst, and pyridine as the solvent.

14. The method of claim 12, wherein the reaction is carried out in the presence of CDI, DCC, DBU, or a combination thereof as the condensing agent, and methylene chloride as the solvent.

15. A herbicidal composition, comprising (i) the 4-pyridinyl formamide compound or derivative thereof 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.

16. A method for controlling a weed, comprising applying a herbicidally effective amount of at least one 4-pyridinyl formamide compound or derivative thereof of claim 1 on a plant or in a weed area.

17. A method for preventing and/or controlling a weed in a useful crop, comprising applying at least one 4-pyridinyl formamide compound or derivative thereof of claim 1 on the useful crop or in a weed area.

18. The method of claim 17, wherein the useful crop is a transgenic crop, or a crop treated by gene editing technique.

19. A method for controlling a weed, comprising applying a herbicidally effective amount of at least one herbicidal composition of claim 15 on a plant or in a weed area.

20. A method for preventing and/or controlling a weed in a useful crop, comprising applying at least one herbicidal composition of claim 15 on the useful crop or in a weed area.

21. The method of claim 20, wherein the useful crop is a transgenic crop, or a crop treated by gene editing technique.