PYRIDAZINOL COMPOUNDS AND DERIVATIVES, PREPARATION METHODS, HERBICIDAL COMPOSITIONS AND APPLICATIONS THEREOF

Information

  • Patent Application
  • 20220312770
  • Publication Number
    20220312770
  • Date Filed
    February 01, 2019
    5 years ago
  • Date Published
    October 06, 2022
    a year ago
Abstract
The invention belongs to the technical field of agricultural chemicals, and in particular relates to a pyridazinol compound represented by the Formula I, a derivative, preparation method, herbicidal composition and use thereof. The compound, derivative and herbicidal composition thereof have very high herbicidal activity and selectivity, and are safe for crops,
Description
TECHNICAL FIELD

The invention belongs to the technical field of agricultural chemicals, and in particular relates to a pyridazinol compound and a derivatives thereof, preparation method, herbicidal composition and application thereof.


BACKGROUND ART

Weed control is a vital part in achieving high-efficiency agriculture. At present, various herbicides are available in the market, such as protoporphyrinogen oxidase inhibitors and photosystem II inhibitors. CN106316962A discloses 3-arylpyridazinone compounds as protoporphyrinogen oxidase inhibitors, which have the structure of




embedded image


and have inhibitory effect on broad-leaved weeds, gramineous weeds and sedgy weeds. In addition, pyridazine herbicides such as Pyridate




embedded image


pyridazinol




embedded image


and the like are photosystem II inhibitors that inhibit photosynthesis by blocking electron transport and conversion of light energy.


Since the continuous expansion of the market, the resistance of weeds, the service life of herbicides and the economical efficiency of herbicides as well as the increasing attention on environmental protection, it is in great demand of constantly research of scientists for developing new herbicides with high-efficiency, safety, economical efficiency and different mechanism of action.


CONTENTS OF THE INVENTION

In order to solve the above problems in the prior art, the present invention provides a pyridazinol compound and a derivative, preparation method, herbicidal composition and use thereof. The compound and the derivative, as well as the composition thereof have very high herbicidal activity and good selectivity, and are safe for crops.


The technical solution adopted by the present invention is as follows:


A pyridazinol compound of Formula I or a derivative thereof:




embedded image


wherein, X is halogenated alkyl, cyano, alkyl, alkoxy, halogenated alkoxy, R1R2N—(C═O)—, R1R2N—, hydroxy, or unsubstituted or substituted aryl;


A is selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, aryl, heteroaryl, and aliphatic heterocyclyl, each of which is unsubstituted or substituted; wherein,


when being substituted, each of the alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, or cycloalkylalkyl is independently substituted with one or more substituents selected from the group consisting of halogen, cyano, nitro, azido, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, —(CH2)n—O—(CH2)p—, —(CH2)n—S—(CH2)p—, —(CH2)n—NR3—(CH2)p—, R—O—, R—O—(CH2)p—O—, R—O—(CH2)p—S—, R—S—, R—S—(CH2)p—O—, R—S—(CH2)p—S—, R—O—(CH2)n—(C═O)—(CH2)q—(O)m—, R—S—(CH2)n—(C═S)—(CH2)q—(S)m—, R—O—(CH2)n—(C═O)—(CH2)q—(S)m—, R—O—(CH2)n—(C═S)—(CH2)q—(O)m—, R—S—(CH2)n—(C═O)—(CH2)q—(O)m—, R—O—(CH2)n—(C═S)—(CH2)q—(S)m—, R—S—(CH2)n—(C═O)—(CH2)q—(S)m—, R—S—(CH2)n—(C═S)—(CH2)q—(O)m—, R—(C═O)—, R—(C═S)—, R—(C═O)—(CH2)n—O—, R—(C═S)—(CH2)n—S—, R—(C═O)—(CH2)n—S—, R—(C═S)—(CH2)n—O—, R—SO—(CH2)n—(O)m—, R—SO—(CH2)n—(S)m—, R—SO—(CH2)n—(NR3)m—, R—SO2—(CH2)n—(O)m—, R—SO2—(CH2)n—(S)m—, R—SO2—(CH2)n—(NR3)m—, R1R2N—, R1R2N—(CH2)n—O—(CH2)q—(O)m—, R1R2N—(CH2)n—O—(CH2)q—(S)m—, R1R2N—(CH2)n—O—(CH2)q—(NR3)m—, R1R2N—(CH2)n—(C═O)—(CH2)q—(O)m—, R1R2N—(CH2)n—(C═O)—(CH2)q—(S)m—, R1R2N—(CH2)n—(C═O)—(CH2)q—(NR3)m—, R1R2N—(CH2)n—SO2—(CH2)q—(O)m—, R1R2N—(CH2)n—SO2—(CH2)q—(S)m—, R1R2N—(CH2)n—SO2—(CH2)q—(NR3)m—, R1R2P(O)—(O)m—, R1R2R3SiO—, R1R2R3Si—(CH═CH)m—, R1R2C═N—(O)m—, and R1R2C═N—NH—;


when being substituted, each of the aryl, heteroaryl, or aliphatic heterocyclyl is substituted with one or more substituents selected from the group consisting of halogen, cyano, nitro, azido, a halogen-containing or not containing group selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, and cycloalkylalkyl, a group selected from aryl, arylalkyl, heteroaryl, heteroarylalkyl, aliphatic heterocyclyl, and aliphatic heterocyclylalkyl, which is unsubstituted or substituted, R—O—(CH2)n—, R—O—(CH2)p—O—(CH2)q—, R—O—(CH2)p—S—(CH2)q—, R—S—(CH2)n—, R—S—(CH2)p—O—(CH2)q—, R—S—(CH2)p—S—(CH2)q—, R—O—(CH2)n—(C═O)—(CH2)q—(O)m—, R—S—(CH2)n—(C═S)—(CH2)q—(S)m—, R—O—(CH2)n—(C═O)—(CH2)q—(S)m—, R—O—(CH2)n—(C═S)—(CH2)q—(O)m—, R—S—(CH2)n—(C═O)—(CH2)q—(O)m—, R—O—(CH2)n—(C═S)—(CH2)q—(S)m—, R—S—(CH2)n—(C═O)—(CH2)q—(S)m—, R—S—(CH2)n—(C═S)—(CH2)q—(O)m—, R—(C═O)—(CH2)n—, R—(C═S)—(CH2)n—, R—(C═O)—(CH2)n—O—(CH2)q—, R—(C═S)—(CH2)n—S—(CH2)q—, R—(C═O)—(CH2)n—S—(CH2)q—, R—(C═S)—(CH2)n—O—(CH2)q—, R—SO—(CH2)n—(O)m—, R—SO—(CH2)n—(S)m—, R—SO—(CH2)n—(NR3)m—, R—SO2—(CH2)n—(O)m—, R—SO2—(CH2)n—(S)m—, R—SO2—(CH2)n—(NR3)m—, R1R2N—(CH2)n—, R1R2N—(CH2)n—O—(CH2)q—(O)m—, R1R2N—(CH2)n—O—(CH2)q—(S)m—, R1R2N—(CH2)n—O—(CH2)q—(NR3)m—, R1R2N—(CH2)n—(C═O)—(CH2)q—(O)m—, R1R2N—(CH2)n—(C═O)—(CH2)q—(S)m—, R1R2N—(CH2)n—(C═O)—(CH2)q—(NR3)m—, R1R2N—(CH2)n—SO2—(CH2)q—(O)m—, R1R2N—(CH2)n—SO2—(CH2)q—(S)m—, R1R2N—(CH2)n—SO2—(CH2)q—(NR3)m—, R1R2PO3—(O)m—(CH2)q—, R1R2R3SiO—(CH2)q—, R1R2R3Si—(CH═CH)m—(CH2)q—, R1R2C═N—(O)m—(CH2)n—, and R1R2C═N—NH—(CH2)n—;


m is 0 or 1, n and q are independently an integer from 0 to 8, p is an integer from 1 to 8;


R is hydrogen, a halogen-containing or not containing group selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, and cycloalkylalkyl, or a group selected from aryl, arylalkyl, heteroaryl, and heteroarylalkyl, which is unsubstituted or substituted;


R1, R2, R3 are each independently hydrogen, nitro, hydroxy, amino, a halogen-containing or not containing group selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkoxyalkyl, alkoxycarbonyl, alkylsulfanylcarbonyl, alkylsulfonyl, alkylsulfonylalkyl, alkylcarbonyl, alkylcarbonylalkyl, alkylcarbonyloxy, alkylamino, alkylaminocarbonyl, alkoxyaminocarbonyl, alkoxycarbonylalkyl, alkylaminocarbonylalkyl, trialkylsilyl, and dialkylphosphonyl, or a group selected from aryl, arylalkyl, aryloxy, arylalkyloxy, aryloxyalkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylalkyloxy, heteroaryloxyalkyl, heteroarylcarbonyl, heteroarylsulfonyl, aliphatic heterocyclyl, aliphatic heterocyclylalkyl, aliphatic heterocyclyloxy, aliphatic heterocyclylalkoxy, aliphatic heterocyclyloxyalkyl, aliphatic heterocyclylcarbonyl, and aliphatic heterocyclylsulfonyl, which is unsubstituted or substituted; or R1R2N— forms a 5- to 6-membered heterocyclyl.


As used in the present application, the term “heteroaryl” refers to an aromatic group, wherein one or more ring atoms, preferable 1, 2, 3 or 4 ring atom, are hetero atoms selected from N, O and S, for example, 5-14 membered heteroaryl, 5-10 membered heteroaryl, 5-9 membered heteroaryl, or 5-6 membered heteroaryl. And when the ring member of the heteroaryl includes a N atom, the heteroaryl substituted with a substituent at the N atom is also included in the scope of the heteroaryl. In a preferred embodiment, the substituent is selected from hydrogen, nitro, hydroxy, amino, a fluoro-, chloro-, or bromo-containing or not containing group selected from C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C1˜C6 alkoxy, C2˜C6 alkenyloxy, C2˜C6 alkynyloxy, C3˜C6 cycloalkyloxy, C1˜C6 alkoxy-C1˜C6 alkyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfanylcarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylsulfonyl-C1˜C6 alkyl, C1˜C6 alkylcarbonyl, C1˜C6 alkylcarbonyl-C1˜C6 alkyl, C1˜C6 alkylcarbonyloxy, C1˜C6 alkylamino, C1˜C6 alkylaminocarbonyl, C1˜C6 alkoxyaminocarbonyl, C1˜C6 alkoxycarbonyl-C1˜C6 alkyl, C1˜C6 alkylaminocarbonyl-C1˜C6 alkyl, triC1˜C6 alkylsilyl, and diC1˜C6 alkylphosphonyl, aryl, aryl-C1˜C6 alkyl, aryloxy, aryl-C1˜C6 alkyloxy, aryloxy-C1˜C6 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1˜C6 alkyl, heteroaryloxy, heteroaryl-C1˜C6 alkyloxy, heteroaryloxy-C1˜C6 alkyl, heteroarylcarbonyl, heteroarylsulfonyl, aliphatic heterocyclyl, aliphatic heterocyclyl-C1˜C6 alkyl, aliphatic heterocyclyloxy, aliphatic heterocyclyl-C1˜C6 alkyloxy, aliphatic heterocyclyloxy-C1˜C6 alkyl, aliphatic heterocyclylcarbonyl, and aliphatic heterocyclylsulfonyl, each of the aryl, aryl-C1˜C6 alkyl, aryloxy, aryl-C1˜C6 alkyloxy, aryloxy-C1˜C6 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1˜C6 alkyl, heteroaryloxy, heteroaryl-C1˜C6 alkyloxy, heteroaryloxy-C1˜C6 alkyl, heteroarylcarbonyl, heteroarylsulfonyl, aliphatic heterocyclyl, aliphatic heterocyclyl-C1˜C6 alkyl, aliphatic heterocyclyloxy, aliphatic heterocyclyl-C1˜C6 alkyloxy, aliphatic heterocyclyloxy-C1˜C6 alkyl, aliphatic heterocyclylcarbonyl, or aliphatic heterocyclylsulfonyl is unsubstituted or substituted with 1˜3 groups independently selected from fluorine, chlorine, bromine, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a fluoro-, chloro-, bromo-containing or not containing group selected from C1˜C6 alkyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C1˜C6 alkoxy, C1˜C6 alkylcarbonyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylamino, and C1˜C6 alkylcarbonyloxy.


In a preferred embodiment, X is halogenated C1˜C8 alkyl, cyano, C1˜C8 alkyl, C1˜C8 alkoxy, halogenated C1˜C8 alkoxy, R1R2N—(C═O)—, R1R2N—, hydroxy, or aryl, the aryl is unsubstituted or substituted with 15 substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C8 alkyl, C3˜C8 cycloalkyl, C3˜C8 cycloalkyl-C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C1˜C8 alkoxy, C1˜C8 alkylcarbonyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylsulfonyl, C1˜C8 alkylamino, and C1˜C8 alkylcarbonyloxy;


A is selected from the group consisting of C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C3˜C8 cycloalkyl, C3˜C8 cycloalkenyl, C3˜C8 cycloalkyl-C1˜C8 alkyl, 5- to 14-membered aryl, 5- to 14-membered heteroaryl, and 5- to 14-membered aliphatic heterocyclyl, each of which is unsubstituted or substituted; wherein,


when being substituted, the C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C3˜C8 cycloalkyl, C3˜C8 cycloalkenyl, or C3˜C8 cycloalkyl-C1˜C8 alkyl is substituted with one or more substituents independently selected from the group consisting of halogen, cyano, nitro, azido, aryl, heteroaryl, the aryl or heteroaryl is unsubstituted or independently substituted with 1˜5 groups selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C8 alkyl, C3˜C8 cycloalkyl, C3˜C8 cycloalkenyl, C3˜C8 cycloalkyl-C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C1˜C8 alkoxy, C1˜C8 alkylcarbonyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylsulfonyl, C1˜C8 alkylamino, and C1˜C8 alkylcarbonyloxy, —(CH2)n—O—(CH2)p—, —(CH2)n—S—(CH2)p—, —(CH2)n—NR3—(CH2)p—, R—O—, R—O—(CH2)p—O—, R—O—(CH2)p—S—, R—S—, R—S—(CH2)p—O—, R—S—(CH2)p—S—, R—O—(C═O)—(CH2)q—(O)m—, R—O—(CH2)n—(C═O)—(O)m—, R—O—(CH2)n—(C═O)—, R—S—(C═S)—(CH2)q—(S)m—, R—S—(CH2)n—(C═S)—(S)m—, R—S—(CH2)n—(C═S)—, R—O—(C═O)—(CH2)q—(S)m—, R—O—(CH2)n—(C═O)—(S)m—, R—O—(C═S)—(CH2)q—(O)m—, R—O—(CH2)n—(C═S)—(O)m—, R—O—(CH2)n—(C═S)—, R—S—(C═O)—(CH2)q—(O)m—, R—S—(CH2)n—(C═O)—(O)m—, R—S—(CH2)n—(C═O)—, R—O—(C═S)—(CH2)q—(S)m—, R—O—(CH2)n—(C═S)—(S)m—, R—S—(C═O)—(CH2)q—(S)m—, R—S—(CH2)n—(C═O)—(S)m—, R—S—(C═S)—(CH2)q—(O)m—, R—S—(CH2)n—(C═S)—(O)m—, R—(C═O)—, R—(C═S)—, R—(C═O)—O—, R—(C═S)—S—, R—(C═O)—S—, R—(C═S)—O—, R—SO—(O)m—, R—SO—(S)m—, R—SO—(NR3)m—, R—SO2—(O)m—, R—SO2—(S)m—, R—SO2(NR3)m—, R1R2N—, R1R2N—O—(CH2)q—(O)m—, R1R2N—(CH2)n—O—, R1R2N—O—(CH2)q—(S)m—, R1R2N—O—(CH2)q—(NR3)m—, R1R2N—(C═O)—(CH2)q—(O)m—, R1R2N—(CH2)n—(C═O)—(O)m—, R1R2N—(CH2)n—(C═O)—, R1R2N—(C═O)—(CH2)q—(S)m—, R1R2N—(CH2)n—(C═O)—(S)m—, R1R2N—(C═O)—(CH2)q—(NR3)m—, R1R2N—(CH2)n—(C═O)—(NR3)m—, R1R2N—SO2—(CH2)q—(O)m—, R1R2N—(CH2)n—SO2—(O)m—, R1R2N—(CH2)n—SO2—, R1R2N—SO2—(CH2)q—(S)m—, R1R2N—(CH2)n—SO2—(S)m—, R1R2N—SO2—(CH2)q—(NR3)m—, R1R2N—(CH2)n—SO2—(NR3)m—, R1R2P(O)—, R1R2R3SiO—, R1R2R3Si—(CH═CH)m—, R1R2C═N—(O)m—, and R1R2C═N—NH—;


when being substituted, each of the 5- to 14-membered aryl, 5- to 14-membered heteroaryl or 5- to 14-membered aliphatic heterocyclyl is independently substituted with one or more substituents selected from the group consisting of halogen, cyano, nitro, azido, a halogen-containing or not containing group selected from C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C3˜C8 cycloalkyl, C3˜C8 cycloalkenyl, and C3˜C8 cycloalkyl-C1˜C8 alkyl, aryl, aryl-C1˜C8 alkyl, heteroaryl, heteroaryl-C1˜C8 alkyl, aliphatic heterocyclyl, aliphatic heterocyclyl-C1˜C8 alkyl, each of the aryl, aryl-C1˜C8 alkyl, heteroaryl, heteroaryl-C1˜C8 alkyl, aliphatic heterocyclyl, or aliphatic heterocyclyl-C1˜C8 alkyl is unsubstituted or substituted with 1˜5 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C8 alkyl, C3˜C8 cycloalkyl, C3˜C8 cycloalkenyl, C3˜C8 cycloalkyl-C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C1˜C8 alkoxy, C1˜C8 alkylcarbonyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylsulfonyl, C1˜C8 alkylamino, and C1˜C8 alkylcarbonyloxy, R—O—(CH2)n—, R—O—(CH2)p—O—(CH2)q—, R—O—(CH2)p—S—(CH2)q—, R—S—(CH2)n—, R—S—(CH2)p—O—(CH2)q—, R—S—(CH2)p—S—(CH2)q—, R—O—(CH2)n—(C═O)—(CH2)q—(O)m—, R—S—(CH2)n—(C═S)—(CH2)q—, R—O—(CH2)n—(C═S)—(CH2)q—, R—S—(CH2)n—(C═O)—(CH2)q—, R—S—(C═S)—(CH2)q—(S)m—, R—O—(CH2)n—(C═O)—(CH2)q—(S)m—, R—O—(C═S)—(CH2)q—(O)m—, R—S—(C═O)—(CH2)q—(O)m—, R—O—(C═S)—(CH2)q—(S)m—, R—S—(C═O)—(CH2)q—(S)m—, R—S—(C═S)—(CH2)q—(O)m—, R—S—(CH2)n—(C═S)—(S)m—, R—O—(CH2)n—(C═S)—(O)m—, R—S—(CH2)n—(C═O)—(O)m—, R—O—(CH2)n—(C═S)—(S)m—, R—S—(CH2)n—(C═O)—(S)m—, R—S—(CH2)n—(C═S)—(O)m—, R—(C═O)—(CH2)n—, R—(C═S)—, R—(C═O)—(CH2)n—O—(CH2)q—, R—(C═S)—(CH2)n—S—, R—(C═O)—(CH2)n—S—, R—(C═S)—(CH2)n—O—, R—(C═S)—S—(CH2)q—, R—(C═O)—S—(CH2)q—, R—(C═S)—O—(CH2)q—, R—SO—(O)m—, R—SO—(S)m—, R—SO—(NR3)m—, R—SO2—(CH2)n—(O)m—, R—SO2—(S)m—, R—SO2—(CH2)n—(NR3)m—, R—SO—(CH2)n—, R1R2N—(CH2)n—, R1R2N—(CH2)n—O—(CH2)q—, R1R2N—(C═O)—(CH2)q—(O)m—, R1R2N—(CH2)n—(C═O)—(CH2)q—, R1R2N—(CH2)n—(C═O)—(O)m—, R1R2N—(CH2)n—(C═O)—(S)m—, R1R2N—(CH2)n—(C═O)—(NR3)m—, R1R2N—(CH2)n—SO2—(CH2)q—(O)m—, R1R2N—(CH2)n—SO2—(S)m—, R1R2N—(CH2)n—SO2—(NR3)m—, R1R2N—(C═O)—(CH2)n—(O)m—, R1R2N—(C═O)—(CH2)n—(S)m—, R1R2N—(C═O)—(CH2)n—(NR3)m—, R1R2N—SO2—(CH2)q—(S)m—, R1R2N—SO2—(CH2)q—(NR3)m—, R1R2N—(CH2)n—O—, R1R2N—O—(CH2)q—, R1R2P(O)—(O)m—, R1R2R3SiO—, R1R2R3Si—(CH═CH)m—, R1R2C═N—(O)m—, and R1R2C═N—NH—;


m is 0 or 1, n and q are independently an integer from 0 to 6, p is an integer from 1 and 6;


R is hydrogen, a halogen-containing or not containing group selected from C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C3˜C8 cycloalkyl, C3˜C8 cycloalkenyl, and C3˜C8 cycloalkyl-C1˜C8 alkyl, aryl, aryl-C1˜C8 alkyl, heteroaryl, or heteroaryl-C1˜C8 alkyl, each of the aryl, aryl-C1˜C8 alkyl, heteroaryl, or heteroaryl-C1˜C8 alkyl is unsubstituted or substituted with 1˜5 groups substituents independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C8 alkyl, C3˜C8 cycloalkyl, C3˜C8 cycloalkenyl, C3˜C8 cycloalkyl-C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C1˜C8 alkoxy, C1˜C8 alkylcarbonyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylsulfonyl, C1˜C8 alkylamino, and C1˜C8 alkylcarbonyloxy;


R1, R2, R3 are each independently hydrogen, nitro, hydroxy, amino, a halogen-containing or not containing group selected from C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C3˜C8 cycloalkyl, C3˜C8 cycloalkenyl, C3˜C8 cycloalkyl-C1˜C8 alkyl, C1˜C8 alkoxy, C2˜C8 alkenyloxy, C2˜C8 alkynyloxy, C3˜C8 cycloalkyloxy, C1˜C8 alkoxy-C1˜C8 alkyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylcarbonyl-C1˜C8 alkyl, C1˜C8 alkylsulfanylcarbonyl, C1˜C8 alkylsulfonyl, C1˜C8 alkylsulfonyl-C1˜C8 alkyl, C1˜C8 alkylcarbonyl, C1˜C8 alkylcarbonyloxy, C1˜C8 alkylamino, C1˜C8 alkylaminocarbonyl, C1˜C8 alkoxyaminocarbonyl, C1˜C8 alkoxycarbonyl-C1˜C8 alkyl, C1˜C8 alkylaminocarbonyl-C1˜C8 alkyl, triC1˜C8 alkylsilyl, and diC1˜C8 alkylphosphonyl, aryl, aryl-C1˜C8 alkyl, aryloxy, aryl-C1˜C8 alkyloxy, aryloxy-C1˜C8 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1˜C8 alkyl, heteroaryloxy, heteroaryl-C1˜C8 alkyloxy, heteroaryloxy-C1˜C8 alkyl, heteroarylcarbonyl, heteroarylsulfonyl, aliphatic heterocyclyl, aliphatic heterocyclyl-C1˜C8 alkyl, aliphatic heterocyclyloxy, aliphatic heterocyclyl-C1˜C8 alkyloxy, aliphatic heterocyclyloxy-C1˜C8 alkyl, aliphatic heterocyclylcarbonyl, or aliphatic heterocyclylsulfonyl, each of the aryl, aryl-C1˜C8 alkyl, aryloxy, aryl-C1˜C8 alkyloxy, aryloxy-C1˜C8 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1˜C8 alkyl, heteroaryloxy, heteroaryl-C1˜C8 alkyloxy, heteroaryloxy-C1˜C8 alkyl, heteroarylcarbonyl, heteroarylsulfonyl, aliphatic heterocyclyl, aliphatic heterocyclyl-C1˜C8 alkyl, aliphatic heterocyclyloxy, aliphatic heterocyclyl-C1˜C8 alkyloxy, aliphatic heterocyclyloxy-C1˜C8 alkyl, aliphatic heterocyclylcarbonyl, or aliphatic heterocyclylsulfonyl is unsubstituted or substituted with 1˜5 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C8 alkyl, C3˜C8 cycloalkyl, C3˜C8 cycloalkenyl, C3˜C8 cycloalkyl-C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C1˜C8 alkoxy, C1˜C8 alkylcarbonyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylsulfonyl, C1˜C8 alkylamino, and C1˜C8 alkylcarbonyloxy; or R1R2N— forms a 5- to 6-membered heterocyclyl;


the derivative is an agriculturally acceptable salt or a compound derivatized from the 4-hydroxy of the pyridazine ring of the Formula I.


In a preferred embodiment, X is halogenated C1˜C6 alkyl;


A is selected from the group consisting of C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, 5- to 14-membered aryl, 5- to 14-membered heteroaryl, and 5- to 14-membered aliphatic heterocyclyl, each of which is unsubstituted or substituted; wherein,


when being substituted, each of the C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, or C3˜C6 cycloalkyl-C1˜C6 alkyl is substituted with one or more substituents independently selected from the group consisting of halogen, cyano, nitro, azido, aryl, heteroaryl, the aryl or heteroaryl is unsubstituted or substituted with 1˜3 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C6 alkyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C1˜C6 alkoxy, C1˜C6 alkylcarbonyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylamino, and C1˜C6 alkylcarbonyloxy, —(CH2)n—O—, —(CH2)n—S—, —(CH2)n—NR3—, R—O—, R—O—(CH2)p—O—, R—O—(CH2)p—S—, R—S—, R—S—(CH2)p—O—, R—S—(CH2)p—S—, R—O—(CH2)n—(C═O)—, R—S—(C═S)—, R—O—(C═S)—, R—S—(C═O)—, R—(C═O)—, R—(C═S)—, R—(C═O)—O—, R—(C═S)—S—, R—(C═O)—S—, R—(C═S)—O—, R—SO—, R—SO2—, R1R2N—, R1R2N—O—, R1R2N—(C═O)—, R1R2N—SO2—, R1R2P(O)—, R1R2R3SiO—, R1R2R3Si—(CH═CH)—, R1R2R3Si—, R1R2C═N—(O)—, R1R2C═N—, and R1R2C═N—NH—;


when being substituted, each of the 5- to 14-membered aryl, 5- to 14-membered heteroaryl or 5- to 14-membered aliphatic heterocyclyl is substituted with one or more substituents independently selected from the group consisting of halogen, cyano, nitro, azido, a halogen-containing or not containing group selected from C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, and C3˜C6 cycloalkyl-C1˜C6 alkyl, aryl, aryl-C1˜C6 alkyl, heteroaryl, heteroaryl-C1˜C6 alkyl, aliphatic heterocyclyl, aliphatic heterocyclyl-C1˜C6 alkyl, each of the aryl, aryl-C1˜C6 alkyl, heteroaryl, heteroaryl-C1˜C6 alkyl, aliphatic heterocyclyl, or aliphatic heterocyclyl-C1˜C6 alkyl is unsubstituted or substituted with 1˜5 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C6 alkyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C1˜C6 alkoxy, C1˜C6 alkylcarbonyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylamino, and C1˜C6 alkylcarbonyloxy, R—O—(CH2)n—, R—O—(CH2)p—O—, R—O—(CH2)p—S—, R—S—(CH2)n—, R—O—(CH2)n—(C═O)—(CH2)q—(O)m—, R—O—(CH2)n—(C═O)—(CH2)q—(S)m—, R—S—(CH2)p—O—, R—S—(CH2)p—S—, R—S—(C═S)—(S)m—, R—O—(C═S)—(O)m—, R—S—(CH2)n—(C═O)—(O)m—, R—O—(C═S)—(S)m—, R—S—(C═O)—(S)m—, R—S—(C═S)—(O)m—, R—S—(C═S)—(CH2)q—, R—O—(C═S)—(CH2)q—, R—S—(C═O)—(CH2)q—, R—S—(CH2)n—(C═S)—, R—O—(CH2)n—(C═S)—, R—S—(CH2)n—(C═O)—, R—(C═O)—(CH2)n—, R—(C═S)—, R—(C═O)—(CH2)n—O—(CH2)q—, R—(C═S)—S—, R—(C═O)—S—, R—(C═S)—O—, R—SO—(CH2)n—, R—SO2—(CH2)n—(O)m—, R—SO2—(CH2)n—(NR3)m—, R1R2N—(CH2)n—, R1R2N—O—, R1R2N—(C═O)—(CH2)q—(O)m—, R1R2N—(C═O)—(S)m—, R1R2N—(C═O)—(NR3)m—, R1R2N—(CH2)n—SO2—(CH2)q—(O)m—, R1R2N—(CH2)p—(C═O)—, R1R2N—(CH2)p—O—, R1R2N—O—(CH2)p—, R1R2P(O)—, R1R2R3SiO—, R1R2R3Si—, R1R2R3Si—CH═CH—, R1R2C═N—, R1R2C═N—O—, and R1R2C═N—NH—;


m is 0 or 1, n and q are each independently an integer from 0 to 4, p is an integer from 1 to 4;


R is hydrogen, a halogen-containing or not containing group selected from C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, and C3˜C6 cycloalkyl-C1˜C6 alkyl, aryl, aryl-C1˜C6 alkyl, heteroaryl, or heteroaryl-C1˜C6 alkyl, each of the aryl, aryl-C1˜C6 alkyl, heteroaryl, or heteroaryl-C1˜C6 alkyl is unsubstituted or substituted with 1˜3 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C6 alkyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C1˜C6 alkoxy, C1˜C6 alkylcarbonyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylamino, and C1˜C6 alkylcarbonyloxy;


R1, R2, R3 are each independently is hydrogen, nitro, hydroxy, amino, a halogen-containing or not containing group selected from C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C1˜C6 alkoxy, C2˜C6 alkenyloxy, C2˜C6 alkynyloxy, C3˜C6 cycloalkyloxy, C1˜C6 alkoxy-C1˜C6 alkyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfanylcarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylsulfonyl-C1˜C6 alkyl, C1˜C6 alkylcarbonyl, C1˜C6 alkylcarbonyl-C1˜C6 alkyl, C1˜C6 alkylcarbonyloxy, C1˜C6 alkylamino, C1˜C6 alkylaminocarbonyl, C1˜C6 alkoxyaminocarbonyl, C1˜C6 alkoxycarbonyl-C1˜C6 alkyl, C1˜C6 alkylaminocarbonyl-C1˜C6 alkyl, triC1˜C6 alkylsilyl, and diC1˜C6 alkylphosphonyl, aryl, aryl-C1˜C6 alkyl, aryloxy, aryl-C1˜C6 alkyloxy, aryloxy-C1˜C6 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1˜C6 alkyl, heteroaryloxy, heteroaryl-C1˜C6 alkyloxy, heteroaryloxy-C1˜C6 alkyl, heteroarylcarbonyl, heteroarylsulfonyl, aliphatic heterocyclyl, aliphatic heterocyclyl-C1˜C6 alkyl, aliphatic heterocyclyloxy, aliphatic heterocyclyl-C1˜C6 alkyloxy, aliphatic heterocyclyloxy-C1˜C6 alkyl, aliphatic heterocyclylcarbonyl, or aliphatic heterocyclylsulfonyl, each of the aryl, aryl-C1˜C6 alkyl, aryloxy, aryl-C1˜C6 alkyloxy, aryloxy-C1˜C6 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1˜C6 alkyl, heteroaryloxy, heteroaryl-C1˜C6 alkyloxy, heteroaryloxy-C1˜C6 alkyl, heteroarylcarbonyl, heteroarylsulfonyl, aliphatic heterocyclyl, aliphatic heterocyclyl-C1˜C6 alkyl, aliphatic heterocyclyloxy, aliphatic heterocyclyl-C1˜C6 alkyloxy, aliphatic heterocyclyloxy-C1˜C6 alkyl, aliphatic heterocyclylcarbonyl, or aliphatic heterocyclylsulfonyl is unsubstituted or substituted with 1˜3 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C6 alkyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C1˜C6 alkoxy, C1˜C6 alkylcarbonyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylamino, and C1˜C6 alkylcarbonyloxy; or R1R2N— is




embedded image


the aryl is selected from




embedded image


the heteroaryl is selected from




embedded image


embedded image


embedded image


R′ is hydrogen, nitro, hydroxy, amino, a fluoro-, chloro-, or bromo-containing or not containing group selected from C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C1˜C6 alkoxy, C2˜C6 alkenyloxy, C2˜C6 alkynyloxy, C3˜C6 cycloalkyloxy, C1˜C6 alkoxy-C1˜C6 alkyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfanylcarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylsulfonyl-C1˜C6 alkyl, C1˜C6 alkylcarbonyl, C1˜C6 alkylcarbonyl-C1˜C6 alkyl, C1˜C6 alkylcarbonyloxy, C1˜C6 alkylamino, C1˜C6 alkylaminocarbonyl, C1˜C6 alkoxyaminocarbonyl, C1˜C6 alkoxycarbonyl-C1˜C6 alkyl, C1˜C6 alkylaminocarbonyl-C1˜C6 alkyl, triC1˜C6 alkylsilyl, and diC1˜C6 alkylphosphonyl, aryl, aryl-C1˜C6 alkyl, aryloxy, aryl-C1˜C6 alkyloxy, aryloxy-C1˜C6 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1˜C6 alkyl, heteroaryloxy, heteroaryl-C1˜C6 alkyloxy, heteroaryloxy-C1˜C6 alkyl, heteroarylcarbonyl, heteroarylsulfonyl, aliphatic heterocyclyl, aliphatic heterocyclyl-C1˜C6 alkyl, aliphatic heterocyclyloxy, aliphatic heterocyclyl-C1˜C6 alkyloxy, aliphatic heterocyclyloxy-C1˜C6 alkyl, aliphatic heterocyclylcarbonyl, or aliphatic heterocyclylsulfonyl, each of the aryl, aryl-C1˜C6 alkyl, aryloxy, aryl-C1˜C6 alkyloxy, aryloxy-C1˜C6 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1˜C6 alkyl, heteroaryloxy, heteroaryl-C1˜C6 alkyloxy, heteroaryloxy-C1˜C6 alkyl, heteroarylcarbonyl, heteroarylsulfonyl, aliphatic heterocyclyl, aliphatic heterocyclyl-C1˜C6 alkyl, aliphatic heterocyclyloxy, aliphatic heterocyclyl-C1˜C6 alkyloxy, aliphatic heterocyclyloxy-C1˜C6 alkyl, aliphatic heterocyclylcarbonyl, or aliphatic heterocyclylsulfonyl is unsubstituted or substituted with 1˜3 groups independently selected from fluorine, chlorine, bromine, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a fluoro-, chloro-, bromo-containing or not containing group selected from C1˜C6 alkyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C1˜C6 alkoxy, C1˜C6 alkylcarbonyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylamino, and C1˜C6 alkylcarbonyloxy;


the aliphatic heterocyclyl is selected from




embedded image


the derivative is an agriculturally acceptable salt or a compound derivatized from 4-hydroxy of the pyridazine ring of the Formula I, including an ester, an oxime, a hydroxylamine and an ether thereof.


In a preferred embodiment, X is halogenated C1˜C6 alkyl;


A is selected from the group consisting of C1˜C6 alkyl, C2˜C6 alkenyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, 5- to 14-membered aryl, 5- to 14-membered heteroaryl, and 5- to 14-membered aliphatic heterocyclyl, each of which is unsubstituted or substituted; wherein,


when being substituted, the C1˜C6 alkyl, C2˜C6 alkenyl, C3˜C6 cycloalkyl, or C3˜C6 cycloalkenyl is substituted with one or more substituents independently selected from R—O—(CH2)n—(C═O)— and R1R2R3SiO—;


when being substituted, the 5- to 14-membered aryl, 5- to 14-membered heteroaryl or 5- to 14-membered aliphatic heterocyclyl is substituted with one or more substituents independently selected from the group consisting of halogen, cyano, nitro, azido, a halogen-containing or not containing group selected from C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, and C3˜C6 cycloalkyl-C1˜C6 alkyl, aryl, aryl-C1˜C6 alkyl, heteroaryl, heteroaryl-C1˜C6 alkyl, aliphatic heterocyclyl, aliphatic heterocyclyl-C1˜C6 alkyl, each of the aryl, aryl-C1˜C6 alkyl, heteroaryl, heteroaryl-C1˜C6 alkyl, aliphatic heterocyclyl, or aliphatic heterocyclyl-C1˜C6 alkyl is unsubstituted or substituted with 1˜5 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C6 alkyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C1˜C6 alkoxy, C1˜C6 alkylcarbonyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylamino, and C1˜C6 alkylcarbonyloxy, R—O—(CH2)n—, R—O—(CH2)p—O—, R—S—(CH2)n—, R—O—(CH2)n—(C═O)—(CH2)q—(O)m—, R—O—(CH2)n—(C═O)—(CH2)q—(S)m—, R—S—(CH2)n—(C═O)—, R—(C═O)—(CH2)n—, R—(C═O)—(CH2)n—O—(CH2)q—, R—SO—(CH2)nR—SO2—(CH2)n—(O)m—, R—SO2—(CH2)n—(NR3)m—, R1R2N—(C═O)—(CH2)q—(O)m—, R1R2N—(C═O)—(NR3)m—, R1R2N—(CH2)n—, R1R2N—(CH2)n—SO2—(CH2)q—, R1R2P(O)—, and R1R2R3Si—;


m is 0 or 1, n and q are each independently an integer from 0 to 4, p is an integer from 1 to 4;


R is hydrogen, a halogen-containing or not containing group selected from C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, and C3˜C6 cycloalkyl-C1˜C6 alkyl, 5- to 14-membered aryl, 5- to 14-membered aryl-C1˜C4 alkyl, or 5- to 14-membered heteroaryl, each of the 5- to 14-membered aryl, 5- to 14-membered aryl-C1˜C4 alkyl, or 5- to 14-membered heteroaryl is unsubstituted or substituted with 1˜3 groups independently selected from halogens;


R1, R2, R3 are each independently hydrogen, nitro, hydroxy, amino, a halogen-containing or not containing group selected from C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, C1˜C6 alkoxy, C1˜C6 alkoxy-C1˜C6 alkyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylcarbonyl, C1˜C6 alkylcarbonyl-C1˜C6 alkyl, and C1˜C6 alkylcarbonyloxy, 5- to 14-membered aryl, 5- to 14-membered aryl-C1˜C6 alkyl, 5- to 14-membered aryloxy, 5- to 14-membered arylcarbonyl, 5- to 14-membered heteroaryl, 5- to 14-membered heteroaryl-C1˜C6 alkyl, 5- to 14-membered heteroaryloxy, 5- to 14-membered heteroarylcarbonyl, or 5- to 14-membered aliphatic heterocyclylcarbonyl, each of the 5- to 14-membered aryl, 5- to 14-membered aryl-C1˜C6 alkyl, 5- to 14-membered aryloxy, 5- to 14-membered arylcarbonyl, 5- to 14-membered heteroaryl, 5- to 14-membered heteroaryl-C1˜C6 alkyl, 5- to 14-membered heteroaryloxy, 5- to 14-membered heteroarylcarbonyl, or 5- to 14-membered aliphatic heterocyclylcarbonyl is unsubstituted or substituted with 1˜3 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C6 alkyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C1˜C6 alkoxy, C1˜C6 alkylcarbonyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylamino, and C1˜C6 alkylcarbonyloxy; or R1R2N— is




embedded image


the aryl is selected from




embedded image


the heteroaryl is selected from




embedded image


embedded image


embedded image


R′ is hydrogen, a fluoro-, chloro-, or bromo-containing or not containing group selected from C1˜C6 alkyl, C1˜C6 alkoxy-C1˜C6 alkyl, C1˜C6 alkoxycarbonyl, and C1˜C6 alkylcarbonyl, aliphatic heterocyclyl, phenyl, or benzyl;


the aliphatic heterocyclyl is selected from




embedded image


the derivative is an agriculturally acceptable salt or a compound derivatized from 4-hydroxy of the pyridazine ring of the Formula I, including an ester, an oxime, a hydroxylamine and an ether thereof.


In a preferred embodiment, X is halogenated C1˜C4 alkyl;


A is selected from the group consisting of C1˜C4 alkyl, C2˜C4 alkenyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, 5- to 14-membered aryl, 5- to 14-membered heteroaryl and 5- to 14-membered aliphatic heterocyclyl, each of which is unsubstituted or substituted; wherein,


when being substituted, the C1˜C4 alkyl, C2˜C4 alkenyl, C3˜C6 cycloalkyl, or C3˜C6 cycloalkenyl is substituted with one or more substituents independently selected from R—O—(C═O)— and R1R2R3SiO—;


when being substituted, the 5- to 14-membered aryl, 5- to 14-membered heteroaryl or 5- to 14-membered aliphatic heterocyclyl is substituted with one or more substituents independently selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, nitro, azido, a fluoro-, chloro- or bromo-containing or not containing group selected from C1˜C4 alkyl, C2˜C4 alkenyl, C2˜C4 alkynyl, C3˜C6 cycloalkyl, and C3˜C6 cycloalkyl-C1˜C4 alkyl, aryl, aryl-C1˜C4 alkyl, heteroaryl, heteroaryl-C1˜C4 alkyl, aliphatic heterocyclyl, each of said aryl, aryl-C1˜C4 alkyl, heteroaryl, heteroaryl-C1˜C4 alkyl, or aliphatic heterocyclyl is unsubstituted or substituted with 1˜3 groups independently selected from fluorine, chlorine, bromine, cyano, hydroxy, and a fluoro-, chloro- or bromo-containing or not containing group selected from C1˜C4 alkyl, C1˜C4 alkoxy, C1˜C4 alkoxycarbonyl, C1˜C4 alkylsulfonyl, and C1˜C4 alkylamino, R—O—(CH2)n—, R—O—CH2—O—, R—S—(CH2)n—, R—O—(CH2)n—(C═O)—, R—O—(CH2)n—(C═O)—O—, R—O—(C═O)—(CH2)q—O—, R—O—(CH2)n—(C═O)—(CH2)q—S—, R—S—(CH2)n—(C═O)—, R—(C═O)—(CH2)n—, R—(C═O)—O—(CH2)q—, R—(C═O)—(CH2)n—O—, R—SO—(CH2)n—, R—SO2—(CH2)n—(O)m—, R—SO2—(CH2)n—NR3—, R1R2N—(C═O)—(CH2)q—, R1R2N—(C═O)—(CH2)q—O—, R1R2N—(C═O)—(NR3)m—, R1R2N—(CH2)n—, R1R2N—(CH2)n—SO2—(CH2)q—, R1R2P(O)—, and R1R2R3Si—;


m is 0 or 1, n and q are each independently an integer from 0, 1, 2 and 3, p is an integer from 1, 2 and 3;


R is hydrogen, a halogen-containing or not containing group selected from C1˜C4 alkyl, C2˜C4 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, and C3˜C6 cycloalkyl-C1˜C4 alkyl, 5- to 14-membered aryl, 5- to 14-membered aryl-C1˜C2 alkyl, or 5- to 6-membered heteroaryl, each of the 5- to 14-membered aryl, 5- to 14-membered aryl-C1˜C2 alkyl, or 5- to 6-membered heteroaryl is unsubstituted or substituted with 1˜3 groups independently selected from fluorine, chlorine, and bromine;


R1, R2, R3 are each independently hydrogen, a fluoro-, chloro- or bromo-containing or not containing group selected from C1˜C4 alkyl, C2˜C4 alkenyl, C2˜C4 alkynyl, C3˜C6 cycloalkyl, C1˜C4 alkoxy, C1˜C4 alkoxyC1˜C4 alkyl, C1˜C4 alkoxycarbonyl, C1˜C4 alkylcarbonyl, C1˜C4 alkylcarbonyl-C1˜C4 alkyl, and C1˜C4 alkylcarbonyloxy, 5- to 14-membered aryl, 5- to 14-membered aryloxy, 5- to 14-membered arylcarbonyl, 5- to 6-membered heteroaryl, 5- to 6-membered heteroaryl-C1˜C4 alkyl, or 5- to 6-membered heteroarylcarbonyl, each of the 5- to 14-membered aryl, 5- to 14-membered aryloxy, 5- to 14-membered arylcarbonyl, 5- to 6-membered heteroaryl, 5- to 6-membered heteroaryl-C1˜C4 alkyl, or 5- to 6-membered heteroarylcarbonyl is unsubstituted or substituted with 1˜3 groups independently selected from fluorine, chlorine, bromine, C1˜C4 alkyl, C1˜C4 alkoxy, C1˜C4 alkylamino, and C3˜C6 cycloalkyl; or R1R2N— is




embedded image


the aryl is selected from




embedded image


the heteroaryl is selected from




embedded image


embedded image


embedded image


R′ is hydrogen, a fluoro-, chloro-, or bromo-containing or not containing group selected from C1˜C4 alkyl, C1˜C4 alkoxy-C1˜C4 alkyl, C1˜C4 alkoxycarbonyl, and C1˜C4 alkylcarbonyl,




embedded image


phenyl, or benzyl;


the aliphatic heterocyclyl is selected from




embedded image


The derivative is an agriculturally acceptable salt or a compound derivatized from 4-hydroxy of the pyridazine ring of the Formula I, including an ester, an oxime, a hydroxylamine and an ether thereof.


In a preferred embodiment, X is CH2F, CHF2, CF3, or CF2CF3;


A is methyl, ethyl,




embedded image


unsubstituted or substituted 5- to 14-membered aryl, unsubstituted or substituted 5- to 14-membered heteroaryl, or unsubstituted or substituted 5- to 14-membered aliphatic heterocyclyl; wherein,


said substituted 5- to 14-membered aryl, substituted 5- to 14-membered heteroaryl or substituted 5- to 14-membered aliphatic heterocyclyl is the 5- to 14-membered aryl, 5- to 14-membered heteroaryl, or 5- to 14-membered aliphatic heterocyclyl, which is substituted with one or more substituents independently selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, nitro, azido, a fluoro-, chloro-, or bromo-containing or not containing group selected from C1˜C4 alkyl, C2˜C4 alkenyl, C2˜C4 alkynyl, C3˜C6 cycloalkyl, and C3˜C6 cycloalkyl-C1˜C2 alkyl, phenyl, pyrrolyl, furyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridyl, pyrazinyl, pyrimidinyl, benzyl, tetrahydropyranyl, thienylmethyl, each of the phenyl, pyrrolyl, furyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridyl, pyrazinyl, pyrimidinyl, benzyl, tetrahydropyranyl, thienylmethyl is unsubstituted or substituted with 13 groups independently selected from fluorine, chlorine, bromine, cyano, hydroxy, and a fluoro-, chloro-, or bromo-containing or not containing group selected from C1˜C4 alkyl, C1˜C4 alkoxy, C1˜C4 alkoxycarbonyl, C1˜C4 alkylsulfonyl, and C1˜C4 alkylamino, R—O—, R—O—CH2—, R—O—CH2CH2—, R—O—CH2—O—, R—O—(C═O)—, R—O—CH2—(C═O)—, R—O—CH2—(C═O)—O—, R—O—(C═O)—CH2—O—, R—O—(C═O)—CH2CH2—O—, R—O—(C═O)—CH2—S—, R—O—CH2—(C═O)—S—, R—O—CH2—(C═O)—CH2—S—, R—S—CH2—, R—S—, R—S—(C═O)—, R—S—CH2—(C═O)—, R—(C═O)—CH2—, R—(C═O)—, R—(C═O)—O—CH2—, R—(C═O)—CH2—O—, R—(C═O)—CH2CH2—O—, R—(C═O)—O—, R—SO—CH2—, R—SO—, R—SO2—CH2—O—, R—SO2—CH2—, R—SO2—O—, R—SO2—, R—SO2—CH2—NR3—, R—SO2—NR3—, R1R2N—CH2—, R1R2N—, R1R2N—(C═O)—CH2—, R1R2N—(C═O)—CH2—O—, R1R2N—(C═O)—, R1R2N—(C═O)—NR3—, R1R2N—CH2—SO2—, R1R2N—CH2—SO2—CH2—, R1R2N—SO2—CH2—, R1R2N—SO2—, R1R2P(O)—, and R1R2R3Si—;


R is hydrogen, a fluoro-, chloro-, or bromo-containing or not containing group selected from C1˜C4 alkyl, C2˜C4 alkenyl, C2˜C4 alkynyl, C3˜C6 cycloalkyl, and C3˜C6 cycloalkyl-C1˜C2 alkyl, phenyl, benzyl, or thienyl, each of the phenyl, benzyl, or thienyl is unsubstituted or substituted with 1˜3 groups independently selected from fluorine, chlorine, and bromine;


R1, R2, R3 are each independently is hydrogen, a fluoro-, chloro-, or bromo-containing or not containing group selected from C1˜C4 alkyl, C2˜C4 alkenyl, C2˜C4 alkynyl, C3˜C6 cycloalkyl, C1˜C4 alkoxy, C1˜C4 alkoxy-C1˜C2 alkyl, C1˜C4 alkoxycarbonyl, C1˜C4 alkylcarbonyl, C1˜C4 alkylcarbonyl-C1˜C2 alkyl, and C1˜C4 alkylcarbonyloxy, phenyl, naphthyl, phenoxy, furyl, thienyl, thiadiazolyl, thienylmethyl, pyrazolylmethyl, benzoyl, or pyridinylformyl, each of the phenyl, naphthyl, phenoxy, furyl, thienyl, thiadiazolyl, thienylmethyl, pyrazolylmethyl, benzoyl, or pyridinylformyl is unsubstituted or substituted with 1˜3 groups independently selected from fluorine, chlorine, bromine, C1˜C4 alkyl, C3˜C6 cycloalkyl, C1˜C4 alkoxy, and C1˜C4 alkylamino; or R1R2N— is




embedded image


the 5- to 14-membered aryl is selected from




embedded image


the heteroaryl is selected from




embedded image


embedded image


embedded image


R′ is hydrogen, a fluoro-, chloro-, or bromo-containing or not containing group selected from C1˜C4 alkyl, C1˜C4 alkoxy-C1˜C2 alkyl, C1˜C4 alkoxycarbonyl, and C1˜C4 alkylcarbonyl,




embedded image


phenyl, or benzyl;


the aliphatic heterocyclyl is




embedded image


the derivative is an agriculturally acceptable salt or a compound derivatized from 4-hydroxy of the pyridazine ring of the Formula I, including an ester, an oxime, a hydroxylamine and an ether thereof.


In a preferred embodiment, X is halogenated alkyl, cyano, alkyl, alkoxy, halogenated alkoxy, R1R2N—(C═O)—, R1R2N—, hydroxy, or unsubstituted or substituted aryl;


A is selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, aryl, and heteroaryl, each of which is unsubstituted or substituted; wherein,


when being substituted, each of the alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, or cycloalkylalkyl is substituted with one or more substituents selected from the group consisting of halogen, cyano, nitro, azido, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, —(CH2)n—O—(CH2)p—, —(CH2)n—S—(CH2)p—, —(CH2)n—NR3—(CH2)p—, R—O—, R—O—(CH2)p—O—, R—O—(CH2)p—S—, R—S—, R—S—(CH2)p—O—, R—S—(CH2)p—S—, R—O—(CH2)n—(C═O)—(CH2)q—(O)m—, R—S—(CH2)n—(C═S)—(CH2)q—(S)m—, R—O—(CH2)n—(C═O)—(CH2)q—(S)m—, R—O—(CH2)n—(C═S)—(CH2)q—(O)m—, R—S—(CH2)n—(C═O)—(CH2)q—(O)m—, R—O—(CH2)n—(C═S)—(CH2)q—(S)m—, R—S—(CH2)n—(C═O)—(CH2)q—(S)m—, R—S—(CH2)n—(C═S)—(CH2)q—(O)m—, R—(C═O)—, R—(C═S)—, R—(C═O)—(CH2)n—O—, R—(C═S)—(CH2)n—S—, R—(C═O)—(CH2)n—S—, R—(C═S)—(CH2)n—O—, R—SO—(CH2)n—(O)m—, R—SO—(CH2)n—(S)m—, R—SO—(CH2)n—(NR3)m—, R—SO2—(CH2)n—(O)m—, R—SO2—(CH2)n—(S)m—, R—SO2—(CH2)n—(NR3)m—, R1R2N—, R1R2N—(CH2)n—O—(CH2)q—(O)m—, R1R2N—(CH2)n—O—(CH2)q—(S)m—, R1R2N—(CH2)n—O—(CH2)q—(NR3)m—, R1R2N—(CH2)n—(C═O)—(CH2)q—(O)m—, R1R2N—(CH2)n—(C═O)—(CH2)q—(S)m—, R1R2N—(CH2)n—(C═O)—(CH2)q—(NR3)m—, R1R2N—(CH2)n—SO2—(CH2)q—(O)m—, R1R2N—(CH2)n—SO2—(CH2)q—(S)m—, R1R2N—(CH2)n—SO2—(CH2)q—(NR3)m—, R1R2PO3—(O)m—, R1R2R3SiO—, R1R2R3Si—(CH═CH)m—, R1R2C═N—(O)m—, and R1R2C═N—NH—;


when being substituted, each of the aryl or heteroaryl is substituted with one or more substituents selected from the group consisting of halogen, cyano, nitro, azido, a halogen-containing or not containing group selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, and cycloalkylalkyl, a group selected from aryl, arylalkyl, heteroaryl, heteroarylalkyl, which is unsubstituted or substituted, R—O—(CH2)n—, R—O—(CH2)p—O—(CH2)q—, R—O—(CH2)p—S—(CH2)q—, R—S—(CH2)n—, R—S—(CH2)p—O—(CH2)q—, R—S—(CH2)p—S—(CH2)q—, R—O—(CH2)n—(C═O)—(CH2)q—(O)m—, R—S—(CH2)n—(C═S)—(CH2)q—(S)m—, R—O—(CH2)n—(C═O)—(CH2)q—(S)m—, R—O—(CH2)n—(C═S)—(CH2)q—(O)m—, R—S—(CH2)n—(C═O)—(CH2)q—(O)m—, R—O—(CH2)n—(C═S)—(CH2)q—(S)m—, R—S—(CH2)n—(C═O)—(CH2)q—(S)m—, R—S—(CH2)n—(C═S)—(CH2)q—(O)m—, R—(C═O)—(CH2)n—, R—(C═S)—(CH2)n—, R—(C═O)—(CH2)n—O—(CH2)q—, R—(C═S)—(CH2)n—S—(CH2)q—, R—(C═O)—(CH2)n—S—(CH2)q—, R—(C═S)—(CH2)n—O—(CH2)q—, R—SO—(CH2)n—(O)m—, R—SO—(CH2)n—(S)m—, R—SO—(CH2)n—(NR3)m—, R—SO2—(CH2)n—(O)m—, R—SO2—(CH2)n—(S)m—, R—SO2—(CH2)n—(NR3)m—, R1R2N—(CH2)n—, R1R2N—(CH2)n—O—(CH2)q—(O)m—, R1R2N—(CH2)n—O—(CH2)q—(S)m—, R1R2N—(CH2)n—O—(CH2)q—(NR3)m—, R1R2N—(CH2)n—(C═O)—(CH2)q—(O)m—, R1R2N—(CH2)n—(C═O)—(CH2)q—(S)m—, R1R2N—(CH2)n—(C═O)—(CH2)q—(NR3)m—, R1R2N—(CH2)n—SO2—(CH2)q—(O)m—, R1R2N—(CH2)n—SO2—(CH2)q—(S)m—, R1R2N—(CH2)n—SO2—(CH2)q—(NR3)m—, R1R2PO3—(O)m—(CH2)q—, R1R2R3SiO—(CH2)q—, R1R2R3Si—(CH═CH)m—(CH2)q—, R1R2C═N—(O)m—(CH2)n—, and R1R2C═N—NH—(CH2)n—;


m is 0 or 1, n and q are independently an integer from 0 to 8, p is an integer from 1 to 8; wherein, m, n, q, p in the above substituents are valued independently, and these values render the substituents different from each other;


R is hydrogen, a halogen-containing or not containing group selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, and cycloalkylalkyl, or a group selected from aryl, arylalkyl, heteroaryl, and heteroarylalkyl, which is unsubstituted or substituted;


R1, R2, R3 are each independently hydrogen, nitro, hydroxy, amino, a halogen-containing or not containing group selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkoxyalkyl, alkoxycarbonyl, alkylsulfanylcarbonyl, alkylsulfonyl, alkylsulfonylalkyl, alkylcarbonyl, alkylcarbonylalkyl, alkylcarbonyloxy, alkylamino, alkylaminocarbonyl, alkoxyaminocarbonyl, alkoxycarbonylalkyl, alkylaminocarbonylalkyl, trialkylsilyl, and dialkylphosphonyl, or a group selected from 6-membered heterocyclyl, aryl, arylalkyl, aryloxy, arylalkyloxy, aryloxyalkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylalkyloxy, heteroaryloxyalkyl, heteroarylcarbonyl, and heteroarylsulfonyl, which is unsubstituted or substituted; or R1R2N— forms a 6-membered heterocyclyl.


In a preferred embodiment, X is halogenated C1˜C8 alkyl, cyano, C1˜C8 alkyl, C1˜C8 alkoxy, halogenated C1˜C8 alkoxy, R1R2N—(C═O)—, R1R2N—, hydroxy, or aryl, the aryl is unsubstituted or substituted with 1-5 substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C8 alkyl, C3˜C8 cycloalkyl, C3˜C8 cycloalkyl-C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C1˜C8 alkoxy, C1˜C8 alkylcarbonyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylsulfonyl, C1˜C8 alkylamino, and C1˜C8 alkylcarbonyloxy;


A is selected from the group consisting of C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C3˜C8 cycloalkyl, C5˜C8 cycloalkenyl, C3˜C8 cycloalkyl-C1˜C8 alkyl, 5- to 14-membered aryl, and 5- to 14-membered heteroaryl, each of which is unsubstituted or substituted; wherein,


when being substituted, the C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C3˜C8 cycloalkyl, C5˜C8 cycloalkenyl, or C3˜C8 cycloalkyl-C1˜C8 alkyl is substituted with one or more substituents independently selected from the group consisting of halogen, cyano, nitro, azido, aryl, heteroaryl, the aryl or heteroaryl is unsubstituted or independently substituted with 15 groups selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C8 alkyl, C3˜C8 cycloalkyl, C5˜C8 cycloalkenyl, C3˜C8 cycloalkyl-C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C1˜C8 alkoxy, C1˜C8 alkylcarbonyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylsulfonyl, C1˜C8 alkylamino, and C1˜C8 alkylcarbonyloxy, —(CH2)n—O—(CH2)p—, —(CH2)n—S—(CH2)p—, —(CH2)n—NR3—(CH2)p—, R—O—, R—O—(CH2)p—O—, R—O—(CH2)p—S—, R—S—, R—S—(CH2)p—O—, R—S—(CH2)p—S—, R—O—(C═O)—(CH2)q—(O)m—, R—O—(CH2)n—(C═O)—(O)m—, R—O—(CH2)n—(C═O)—, R—S—(C═S)—(CH2)q—(S)m—, R—S—(CH2)n—(C═S)—(S)m—, R—S—(CH2)n—(C═S)—, R—O—(C═O)—(CH2)q—(S)m—, R—O—(CH2)n—(C═O)—(S)m—, R—O—(C═S)—(CH2)q—(O)m—, R—O—(CH2)n—(C═S)—(O)m—, R—O—(CH2)n—(C═S)—, R—S—(C═O)—(CH2)q—(O)m—, R—S—(CH2)n—(C═O)—(O)m—, R—S—(CH2)n—(C═O)—, R—O—(C═S)—(CH2)q—(S)m—, R—O—(CH2)n—(C═S)—(S)m—, R—S—(C═O)—(CH2)q—(S)m—, R—S—(CH2)n—(C═O)—(S)m—, R—S—(C═S)—(CH2)q—(O)m—, R—S—(CH2)n—(C═S)—(O)m—, R—(C═O)—, R—(C═S)—, R—(C═O)—O—, R—(C═S)—S—, R—(C═O)—S—, R—(C═S)—O—, R—SO—(O)m—, R—SO—(S)m—, R—SO—(NR3)m—, R—SO2—(O)m—, R—SO2—(S)m—, R—SO2(NR3)m—, R1R2N—, R1R2N—O—(CH2)q—(O)m—, R1R2N—(CH2)n—O—, R1R2N—O—(CH2)q—(S)m—, R1R2N—O—(CH2)q—(NR3)m—, R1R2N—(C═O)—(CH2)q—(O)m—, R1R2N—(CH2)n—(C═O)—(O)m—, R1R2N—(CH2)n—(C═O)—, R1R2N—(C═O)—(CH2)q—(S)m—, R1R2N—(CH2)n—(C═O)—(S)m—, R1R2N—(C═O)—(CH2)q—(NR3)m—, R1R2N—(CH2)n—(C═O)—(NR3)m—, R1R2N—SO2—(CH2)q—(O)m—, R1R2N—(CH2)n—SO2—(O)m—, R1R2N—(CH2)n—SO2—, R1R2N—SO2—(CH2)q—(S)m—, R1R2N—(CH2)n—SO2—(S)m—, R1R2N—SO2—(CH2)q—(NR3)m—, R1R2N—(CH2)n—SO2—(NR3)m—, R1R2PO3—, R1R2R3SiO—, R1R2R3Si—(CH═CH)m—, R1R2C═N—(O)m—, and R1R2C═N—NH—;


when being substituted, each of the 5- to 14-membered aryl or 5- to 14-membered heteroaryl is independently substituted with one or more substituents selected from the group consisting of halogen, cyano, nitro, azido, a halogen-containing or not containing group selected from C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C3˜C8 cycloalkyl, C5˜C8 cycloalkenyl, and C3˜C8 cycloalkyl-C1˜C8 alkyl, aryl, aryl-C1˜C8 alkyl, heteroaryl, heteroaryl-C1˜C8 alkyl, each of the aryl, aryl-C1˜C8 alkyl, heteroaryl, or heteroaryl-C1˜C8 alkyl is unsubstituted or substituted with 1˜5 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C8 alkyl, C3˜C8 cycloalkyl, C5˜C8 cycloalkenyl, C3˜C8 cycloalkyl-C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C1˜C8 alkoxy, C1˜C8 alkylcarbonyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylsulfonyl, C1˜C8 alkylamino, and C1˜C8 alkylcarbonyloxy, R—O—(CH2)n—, R—O—(CH2)p—O—(CH2)q—, R—O—(CH2)p—S—(CH2)q—, R—S—(CH2)n—, R—S—(CH2)p—O—(CH2)q—, R—S—(CH2)p—S—(CH2)q—, R—O—(CH2)n—(C═O)—(CH2)q—, R—S—(CH2)n—(C═S)—(CH2)q—, R—O—(CH2)n—(C═S)—(CH2)q—, R—S—(CH2)n—(C═O)—(CH2)q—, R—O—(C═O)—(CH2)q—(O)m—, R—S—(C═S)—(CH2)q—(S)m—, R—O—(C═O)—(CH2)q—(S)m—, R—O—(C═S)—(CH2)q—(O)m—, R—S—(C═O)—(CH2)q—(O)m—, R—O—(C═S)—(CH2)q—(S)m—, R—S—(C═O)—(CH2)q—(S)m—, R—S—(C═S)—(CH2)q—(O)m—, R—O—(CH2)n—(C═O)—(O)m—, R—S—(CH2)n—(C═S)—(S)m—, R—O—(CH2)n—(C═O)—(S)m—, R—O—(CH2)n—(C═S)—(O)m—, R—S—(CH2)n—(C═O)—(O)m—, R—O—(CH2)n—(C═S)—(S)m—, R—S—(CH2)n—(C═O)—(S)m—, R—S—(CH2)n—(C═S)—(O)m—, R—(C═O)—, R—(C═S)—, R—(C═O)—(CH2)n—O—, R—(C═S)—(CH2)n—S—, R—(C═O)—(CH2)n—S—, R—(C═S)—(CH2)n—O—, R—(C═O)—O—(CH2)q—, R—(C═S)—S—(CH2)q—, R—(C═O)—S—(CH2)q—, R—(C═S)—O—(CH2)q—, R—SO—(O)m—, R—SO—(S)m—, R—SO—(NR3)m—, R—SO2—(O)m—, R—SO2—(S)m—, R—SO2—(NR3)m—, R—SO—(CH2)n—, R—SO2—(CH2)n—, R1R2N—, R1R2N—(CH2)n—O—(CH2)q—, R1R2N—(CH2)n—(C═O)—(CH2)q—, R1R2N—(CH2)n—SO2—(CH2)q—, R1R2N—(CH2)n—(C═O)—(O)m—, R1R2N—(CH2)n—(C═O)—(S)m—, R1R2N—(CH2)n—(C═O)—(NR3)m—, R1R2N—(CH2)n—SO2—(O)m—, R1R2N—(CH2)n—SO2—(S)m—, R1R2N—(CH2)n—SO2—(NR3)m—, R1R2N—(C═O)—(CH2)n—(O)m—, R1R2N—(C═O)—(CH2)n—(S)m—, R1R2N—(C═O)—(CH2)n—(NR3)m—, R1R2N—SO2—(CH2)q—(O)m—, R1R2N—SO2—(CH2)q—(S)m—, R1R2N—SO2—(CH2)q—(NR3)m—, R1R2N—(CH2)n—O—, R1R2N—O—(CH2)q—, R1R2PO3—(O)m—, R1R2R3SiO—, R1R2R3Si—(CH═CH)m—, R1R2C═N—(O)m—, and R1R2C═N—NH—;


m is 0 or 1, n and q are independently an integer from 0 to 6, p is an integer from 1 to 6; wherein, m, n, q, p in the above substituents are valued independently, and these values render the substituents different from each other;


R is hydrogen, a halogen-containing or not containing group selected from C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C3˜C8 cycloalkyl, C5˜C8 cycloalkenyl, and C3˜C8 cycloalkyl-C1˜C8 alkyl, aryl, aryl-C1˜C8 alkyl, heteroaryl, or heteroaryl-C1˜C8 alkyl, each of the aryl, aryl-C1˜C8 alkyl, heteroaryl, or heteroaryl-C1˜C8 alkyl is unsubstituted or substituted with 1-5 groups substituents independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C8 alkyl, C3˜C8 cycloalkyl, C5˜C8 cycloalkenyl, C3˜C8 cycloalkyl-C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C1˜C8 alkoxy, C1˜C8 alkylcarbonyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylsulfonyl, C1˜C8 alkyl amino, and C1˜C8 alkylcarbonyloxy;


R1, R2, R3 are each independently hydrogen, nitro, hydroxy, amino, a halogen-containing or not containing group selected from C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C3˜C8 cycloalkyl, C5˜C8 cycloalkenyl, C3˜C8 cycloalkyl-C1˜C8 alkyl, C1˜C8 alkoxy, C2˜C8 alkenyloxy, C2˜C8 alkynyloxy, C3˜C8 cycloalkyloxy, C1˜C8 alkoxy-C1˜C8 alkyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylcarbonyl-C1˜C8 alkyl, C1˜C8 alkylsulfanylcarbonyl, C1˜C8 alkylsulfonyl, C1˜C8 alkylsulfonyl-C1˜C8 alkyl, C1˜C8 alkylcarbonyl, C1˜C8 alkylcarbonyloxy, C1˜C8 alkylamino, C1˜C8 alkylaminocarbonyl, C1˜C8 alkoxyaminocarbonyl, C1˜C8 alkoxycarbonyl-C1˜C8 alkyl, C1˜C8 alkylaminocarbonyl-C1˜C8 alkyl, triC1˜C8 alkylsilyl, and diC1˜C8 alkylphosphonyl, 6-membered heterocyclyl, aryl, aryl-C1˜C8 alkyl, aryloxy, aryl-C1˜C8 alkyloxy, aryloxy-C1˜C8 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1˜C8 alkyl, heteroaryloxy, heteroaryl-C1˜C8 alkyloxy, heteroaryloxy-C1˜C8 alkyl, heteroarylcarbonyl, or heteroarylsulfonyl, each of the 6-membered heterocyclyl, aryl, aryl-C1˜C8 alkyl, aryloxy, aryl-C1˜C8 alkyloxy, aryloxy-C1˜C8 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1˜C8 alkyl, heteroaryloxy, heteroaryl-C1˜C8 alkyloxy, heteroaryloxy-C1˜C8 alkyl, heteroarylcarbonyl, or heteroarylsulfonyl is unsubstituted or substituted with 1-5 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C8 alkyl, C3˜C8 cycloalkyl, C5˜C8 cycloalkenyl, C3˜C8 cycloalkyl-C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C1˜C8 alkoxy, C1˜C8 alkylcarbonyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylsulfonyl, C1˜C8 alkylamino, and C1˜C8 alkylcarbonyloxy; or R1R2N— forms a 6-membered heterocyclyl containing or not containing other hetero atoms.


In a preferred embodiment, X is halogenated C1˜C6 alkyl;


A is selected from the group consisting of C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, C5˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, 5- to 14-membered aryl, and 5- to 14-membered heteroaryl, each of which is unsubstituted or substituted; wherein,


when being substituted, each of the C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, C5˜C6 cycloalkenyl, or C3˜C6 cycloalkyl-C1˜C6 alkyl is substituted with one or more substituents independently selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, azido, aryl, heteroaryl, the aryl or heteroaryl is unsubstituted or substituted with 1˜3 groups independently selected from fluorine, chlorine, bromine, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a fluoro-, chloro-, or bromo-containing or not containing group selected from C1˜C6 alkyl, C3˜C6 cycloalkyl, C5˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C1˜C6 alkoxy, C1˜C6 alkylcarbonyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylamino, and C1˜C6 alkylcarbonyloxy, —(CH2)n—O—, —(CH2)n—S—, —(CH2)n—NR3—, R—O—, R—O—(CH2)p—O—, R—O—(CH2)p—S—, R—S—, R—S—(CH2)p—O—, R—S—(CH2)p—S—, R—O—(C═O)—, R—S—(C═S)—, R—O—(C═S)—, R—S—(C═O)—, R—(C═O)—, R—(C═S)—, R—(C═O)—O—, R—(C═S)—S—, R—(C═O)—S—, R—(C═S)—O—, R—SO—, R—SO2—, R1R2N—, R1R2N—O—, R1R2N—(C═O)—, R1R2N—SO2—, R1R2PO3—, R1R2R3SiO—, R1R2R3Si—(CH═CH)—, R1R2R3Si—, R1R2C═N—(O)—, R1R2C═N—, and R1R2C═N—NH—;


when being substituted, each of the 5- to 14-membered aryl or 5- to 14-membered heteroaryl is substituted with one or more substituents independently selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, azido, a fluoro-, chloro-, or bromo-containing or not containing group selected from C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, C5˜C6 cycloalkenyl, and C3˜C6 cycloalkyl-C1˜C6 alkyl, aryl, aryl-C1˜C6 alkyl, heteroaryl, heteroaryl-C1˜C6 alkyl, each of the aryl, aryl-C1˜C6 alkyl, heteroaryl, or heteroaryl-C1˜C6 alkyl is unsubstituted or substituted with 1˜3 groups independently selected from fluorine, chlorine, bromine, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a fluoro-, chloro-, or bromo-containing or not containing group selected from C1˜C6 alkyl, C3˜C6 cycloalkyl, C5˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C1˜C6 alkoxy, C1˜C6 alkylcarbonyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylamino, and C1˜C6 alkylcarbonyloxy, R—O—, R—O—(CH2)p—O—, R—O—(CH2)p—S—, R—S—, R—S—(CH2)p—O—, R—S—(CH2)p—S—, R—O—(C═O)—(O)m—, R—S—(C═S)—(S)m—, R—O—(C═O)—(S)m—, R—O—(C═S)—(O)m—, R—S—(C═O)—(O)m—, R—O—(C═S)—(S)m—, R—S—(C═O)—(S)m—, R—S—(C═S)—(O)m—, R—O—(C═O)—(CH2)q—, R—S—(C═S)—(CH2)q—, R—O—(C═S)—(CH2)q—, R—S—(C═O)—(CH2)q—, R—O—(CH2)n—(C═O)—, R—S—(CH2)n—(C═S)—, R—O—(CH2)n—(C═S)—, R—S—(CH2)n—(C═O)—, R—(C═O)—, R—(C═S)—, R—(C═O)—O—, R—(C═S)—S—, R—(C═O)—S—, R—(C═S)—O—, R—SO—, R—SO2—, R1R2N—, R1R2N—O—, R1R2N—(C═O)—(CH2)p—, R1R2N—(C═O)—(O)m—, R1R2N—(C═O)—(S)m—, R1R2N—(C═O)—(NR3)m—, R1R2N—SO2—(CH2)p—, R1R2N—SO2—, R1R2N—(CH2)p—(C═O)—, R1R2N—(CH2)p—SO2—, R1R2N—(CH2)p—O—, R1R2N—O—(CH2)p—, R1R2PO3—, R1R2R3SiO—, R1R2R3Si—, R1R2R3Si—CH═CH—, R1R2C═N—, R1R2C═N—O—, and R1R2C═N—NH—;


m is 0 or 1, n and q are each independently an integer from 0 to 4, p is an integer from 1 to 4; wherein, m, n, q, p in the above substituents are valued independently, and these values render the substituents different from each other;


R is hydrogen, a halogen-containing or not containing group selected from C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, C5˜C6 cycloalkenyl, and C3˜C6 cycloalkyl-C1˜C6 alkyl, aryl, aryl-C1˜C6 alkyl, heteroaryl, or heteroaryl-C1˜C6 alkyl, each of the aryl, aryl-C1˜C6 alkyl, heteroaryl, or heteroaryl-C1˜C6 alkyl is unsubstituted or substituted with 1˜3 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C6 alkyl, C3˜C6 cycloalkyl, C5˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C1˜C6 alkoxy, C1˜C6 alkylcarbonyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylamino, and C1˜C6 alkylcarbonyloxy;


R1, R2, R3 are each independently is hydrogen, nitro, hydroxy, amino, a fluoro-, chloro-, or bromo-containing or not containing group selected from C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, C5˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C1˜C6 alkoxy, C2˜C6 alkenyloxy, C2˜C6 alkynyloxy, C3˜C6 cycloalkyloxy, C1˜C6 alkoxy-C1˜C6 alkyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfanylcarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylsulfonyl-C1˜C6 alkyl, C1˜C6 alkylcarbonyl, C1˜C6 alkylcarbonyl-C1˜C6 alkyl, C1˜C6 alkylcarbonyloxy, C1˜C6 alkylamino, C1˜C6 alkylaminocarbonyl, C1˜C6 alkoxyaminocarbonyl, C1˜C6 alkoxycarbonyl-C1˜C6 alkyl, C1˜C6 alkylaminocarbonyl-C1˜C6 alkyl, triC1˜C6 alkylsilyl, and diC1˜C6 alkylphosphonyl,




embedded image


aryl, aryl-C1˜C6 alkyl, aryloxy, aryl-C1˜C6 alkyloxy, aryloxy-C1˜C6 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1˜C6 alkyl, heteroaryloxy, heteroaryl-C1˜C6 alkyloxy, heteroaryloxy-C1˜C6 alkyl, heteroarylcarbonyl, or heteroarylsulfonyl, each of the




embedded image


aryl, aryl-C1˜C6 alkyl, aryloxy, aryl-C1˜C6 alkyloxy, aryloxy-C1˜C6 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1˜C6 alkyl, heteroaryloxy, heteroaryl-C1˜C6 alkyloxy, heteroaryloxy-C1˜C6 alkyl, heteroarylcarbonyl, or heteroarylsulfonyl is unsubstituted or substituted with 1˜3 groups independently selected from fluorine, chlorine, bromine, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a fluoro-, chloro-, or bromo-containing or not containing group selected from C1˜C6 alkyl, C3˜C6 cycloalkyl, C5˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C1˜C6 alkoxy, C1˜C6 alkylcarbonyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylamino, and C1˜C6 alkylcarbonyloxy; or R1R2N— is




embedded image


the aryl is selected from




embedded image


the heteroaryl is selected from




embedded image


embedded image


embedded image


R′ is hydrogen, nitro, hydroxy, amino, a fluoro-, chloro-, or bromo-containing or not containing group selected from C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, C5˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C1˜C6 alkoxy, C2˜C6 alkenyloxy, C2˜C6 alkynyloxy, C3˜C6 cycloalkyloxy, C1˜C6 alkoxy-C1˜C6 alkyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfanylcarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylsulfonyl-C1˜C6 alkyl, C1˜C6 alkylcarbonyl, C1˜C6 alkylcarbonyl-C1˜C6 alkyl, C1˜C6 alkylcarbonyloxy, C1˜C6 alkylamino, C1˜C6 alkylaminocarbonyl, C1˜C6 alkoxyaminocarbonyl, C1˜C6 alkoxycarbonyl-C1˜C6 alkyl, C1˜C6 alkylaminocarbonyl-C1˜C6 alkyl, triC1˜C6 alkylsilyl, and diC1˜C6 alkylphosphonyl,




embedded image


aryl, aryl-C1˜C6 alkyl, aryloxy, aryl-C1˜C6 alkyloxy, aryloxy-C1˜C6 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1˜C6 alkyl, heteroaryloxy, heteroaryl-C1˜C6 alkyloxy, heteroaryloxy-C1˜C6 alkyl, heteroarylcarbonyl, or heteroarylsulfonyl, each of the




embedded image


aryl, aryl-C1˜C6 alkyl, aryloxy, aryl-C1˜C6 alkyloxy, aryloxy-C1˜C6 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1˜C6 alkyl, heteroaryloxy, heteroaryl-C1˜C6 alkyloxy, heteroaryloxy-C1˜C6 alkyl, heteroarylcarbonyl, or heteroarylsulfonyl is unsubstituted or substituted with 1˜3 groups independently selected from fluorine, chlorine, bromine, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a fluoro-, chloro-, bromo-containing or not containing group selected from C1˜C6 alkyl, C3˜C6 cycloalkyl, C5˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C1˜C6 alkoxy, C1˜C6 alkylcarbonyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylamino, and C1˜C6 alkylcarbonyloxy;


wherein,




embedded image


may bond to any site (e.g. C atom) of the above mentioned aryl or heteroaryl, and when R′ is H, it may bond to N atom.


In a preferred embodiment, X is CH2F, CHF2, CF3, or CF2CF3;


A is




embedded image


or a unsubstituted or substituted group, wherein the group is selected from methyl, ethyl, vinyl, propenyl,




embedded image


wherein,


the substituted methyl, ethyl, vinyl, propenyl,




embedded image


refers to being substituted with one or more substituents independently selected from the group consisting of fluorine, chlorine, bromine, cyano, R—O—, R—O—(C═O)—, R—(C═O)—, R—(C═O)—O—, R—SO2—, R1R2N—, R1R2N—(C═O)—, R1R2N—SO2—, R1R2PO3—, R1R2R3SiO—, R1R2R3Si—(CH═CH)—, R1R2R3Si—, R1R2C═N—(O)—, R1R2C═N—, and R1R2C═N—NH—;


R is the substituted




embedded image


refers to being substituted with one or more substituents selected from the group consisting of fluorine, chlorine, bromine, cyano, nitro, azido, a fluoro-, chloro-, or bromo-containing or not containing group selected from C1˜C6alkyl, and C3˜C6 cycloalkyl, phenyl, benzyl, the phenyl or benzyl is unsubstituted or substituted from 1˜3 substituents selected from fluorine, chlorine, bromine, cyano, nitro, amino, and a fluoro-, chloro-, or bromo-containing or not containing group selected from C1˜C6 alkyl, C3˜C6 cycloalkyl, C1˜C6 alkoxyl, C1˜C6 alkylcarbonyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylamino, and C1˜C6 alkylcarbonyloxy, R—O—, R—O—(C═O)—, R—(C═O)—, R—(C═O)—O—, R—SO2—, R1R2N—, R1R2N—(C═O)—, R1R2N—SO2—, R1R2PO3—, R1R2R3SiO—, R1R2R3Si—, R1R2R3Si—CH═CH—, R1R2C═N—, R1R2C═N—O—, and R1R2C═N—NH—;


m is 0 or 1, n and q are independently 0, 1, or 2, p is 1 or 2;


R is hydrogen, a fluoro-, chloro-, or bromo-containing or not containing group selected from C1˜C6 alkyl, and C3˜C6 cycloalkyl, phenyl, or benzyl, each of the phenyl or benzyl is unsubstituted or substituted with 13 groups independently selected from fluorine, chlorine, bromine, cyano, nitro, amino, and a fluoro-, chloro-, or bromo-containing or not containing group selected from C1˜C6 alkyl, C3˜C6 cycloalkyl, C1˜C6 alkoxy, C1˜C6 alkylcarbonyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylamino, and C1˜C6 alkylcarbonyloxy;


R1, R2, R3 are each independently is hydrogen, a fluoro-, chloro-, or bromo-containing or not containing group selected from C1˜C6 alkyl, C3˜C6 cycloalkyl, C1˜C6 alkoxy, C1˜C6 alkoxy-C1˜C6 alkyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylsulfonyl-C1˜C6 alkyl, C1˜C6 alkylcarbonyl, C1˜C6 alkylcarbonyl-C1˜C6 alkyl, C1˜C6 alkylcarbonyloxy, C1˜C6 alkylamino, C1˜C6 alkylaminocarbonyl, C1˜C6 alkoxylaminocarbonyl, C1˜C6 alkoxylcarbonyl-C1˜C6 alkyl, and C1˜C6 alkylaminocarbonyl-C1˜C6 alkyl, phenyl, benzyl,




embedded image


the phenyl, benzyl,




embedded image


is unsubstituted or substituted with 13 groups independently selected from fluorine, chlorine, bromine, cyano, nitro, amino, and a fluoro-, chloro-, or bromo-containing or not containing group selected from C1˜C6 alkyl, C3˜C6 cycloalkyl, C1˜C6 alkoxy, C1˜C6 alkylcarbonyl, C1˜C6 alkoxylcarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylamino, and C1˜C6 alkylcarbonyloxy; or R1R2N— is




embedded image


R′ is hydrogen or C1-6alkyl.


In addition, when X represents —CH2Cl in Formula I, A is not —CH2Cl.


In the present invention, the derivative




embedded image


is an agriculturally acceptable salt or a compound derivatized from the 4-hydroxy of the pyridazine ring of Formula I, including derivatives such as an ester, a hydrazine, a hydroxylamine and an ether thereof.


The agriculturally acceptable salt is a salt commonly used in agricultural chemicals, for example, the pyridazaine compound or the derivative may be processed into an alkali metal salt, an alkaline earth metal salt or an amine 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 “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, more preferably, ethanolamine salt, dimethylethanolamine salt, triethanolamine salt, dimethylamine salt, triethylamine salt, isopropylamine salt, choline salt or diglycolamine salt.


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


The compound of the present invention may also have a chiral carbon atom. In this case, the present invention also includes an optical isomer and a mixture of optical isomers in any ratio.


The ester derivative refers to a compound having an ester moiety formed by derivatization of the 4-hydroxy of the pyridazine ring, that is, the M group in Formula I-1 may be acyl, thioacyl, sulfoxide, sulfonyl, phosphoryl, thiophosphoryl, etc., and other groups are as defined above in Formula I.


For example, the M group in Formula I-1 may be (thio)formyl, C1˜C18 alkyl(thio)carbonyl, wherein the (thio)formyl, or C1˜C18 alkyl(thio)carbonyl is optionally substituted by a substituent [the substituent is one or more same or different substituents selected from halogen, amino, C3˜C8 cycloalkyl, C1˜C8 alkoxy, C1˜C8 alkylsulfanyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylcarbonyloxy, C1˜C8 alkylcarbonyl, and C2˜C8 alkenyloxycarbonyl optionally substituted by a substituent {the substituent is 1˜3 same or different substituents selected from C3˜C8 cycloalkyl, cyano, and benzoyl optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from halogen, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C1˜C8 alkoxycarbonyl, nitro and C1˜C8 alkylsulfonyl)}, hydroxy(methyl)phosphinyl, C3˜C8 cycloalkenyloxycarbonyl optionally substituted by a substituent {the substituent is 1˜2 same or different substituents selected from oxo and benzoyl optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C1˜C8 alkoxycarbonyl, nitro and C1˜C8 alkylsulfonyl)}, 5- or 6-membered heterocyclyloxycarbonyl optionally substituted by a substituent {the ring of the heterocyclyl contains one nitrogen atom, oxygen atom or sulfur atom, and may further contain one or two nitrogen atoms, the substituent is 1˜3 same or different substituents selected from halogen, a C1˜C8 alkyl, phenoxy optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from halogen, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C3˜C8 cycloalkyl and C1˜C8 alkoxycarbonyl), 2,3-dihydro-1H-indenyloxy, and benzoyl optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from halogen, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C1˜C8 alkoxycarbonyl, nitro and C1˜C8 alkylsulfonyl)}, phenyl, phenoxy, benzyloxy, phenylsulfanyl, benzylsulfanyl, wherein the phenyl, phenoxy, benzyloxy, phenylsulfanyl, or benzylsulfanyl is optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from halogen, C1˜C8 alkyl, C1˜C8 alkoxy, C1˜C8 halogenated alkyl, and C1˜C8 alkoxycarbonyl), and C1˜C8 alkylsulfanyl], C3˜C8cycloalkyl(thio)carbonyl, adamantyl(thio)carbonyl, C2˜C8 alkenyl(thio)carbonyl optionally substituted by a substituent {the substituent is one or more same or different substituents selected from halogen, C1˜C8 alkoxy, phenyl, phenylsulfanyl, and phenoxy optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from halogen, C1˜C8 alkyl, C1˜C8 alkoxy, C1˜C8 halogenated alkyl, and C1˜C8 alkoxycarbonyl)}, C2˜C8 alkynyl(thio)carbonyl, (thio)benzoyl, (thio)naphthoyl, wherein the (thio)benzoyl or (thio)naphthoyl is optionally substituted by a substitutent [the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl optionally substituted by a substituent (the substituent is one or more same or different substituents selected from halogen and phenyl), cyano, hydroxy, C1˜C8 alkylcarbonyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylcarbonyloxy, C1˜C8 alkylcarbonylamino, amino optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from C1˜C8 alkyl, C1˜C8 alkoxy, C1˜C8 alkylcarbonyl, halogenated C1˜C8 alkyl and phenyl), C2˜C8 alkenyloxycarbonyl optionally substituted by a substituent {the substituent is 1˜3 same or different substituents selected from C3˜C8 cycloalkyl, cyano, and benzoyl optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from halogen, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C1˜C8 alkoxycarbonyl, nitro, and C1˜C8 alkylsulfonyl)}, C3˜C8 cycloalkenyloxycarbonyl optionally substituted by a substituent {the substituent is 1˜2 same or different substituents selected from oxo, and benzoyl optionally substituted by a substituent (the substituent is 1-3 same or different substituents selected from halogen, C1˜C8 alkyl, halogenated C1˜C8 alkyl, C1˜C8 alkoxycarbonyl, nitro, and C1˜C8 alkylsulfonyl)}, phenyl, nitro, C1˜C8 alkoxy optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from halogen and phenyl), phenoxy, 5- or 6-membered heterocyclyloxycarbonyl optionally substituted by a substituent {the ring of the heterocyclyl contains 1 nitrogen atom, oxygen atom or sulfur atom, and may further contain 1 to 2 nitrogen atoms, the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, phenoxy optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from halogen, C1˜C8 alkyl, halogenated C1˜C8 alkyl, C3˜C8 cycloalkyl, and C1˜C8 alkoxycarbonyl), 2,3-dihydro-1H-indenyloxy, and benzoyl optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from halogen, C1˜C8 alkyl, halogenated C1˜C8 alkyl, C1˜C8 alkoxycarbonyl, nitro, and C1˜C8 alkylsulfonyl)}, and 5- or 6-membered heterocyclyloxysulfonyl optionally substituted by a substituent {the ring of the heterocyclyl contains 1 nitrogen atom, oxygen atom or sulfur atom, and may further contain 1 to 2 nitrogen atoms, the substituent is 1˜3 same or different substituents selected from halogen, C1˜C8 alkyl, phenoxy optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from halogen, C1˜C8 alkyl, halogenated C1˜C8 alkyl, C3˜C8cycloalkyl, and C1˜C8 alkoxycarbonyl), 2,3-dihydro-1H-indenyloxy, and benzoyl optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from halogen, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C1˜C8 alkoxycarbonyl, nitro, and C1˜C8 alkylsulfonyl)}], halogen-substituted sulfhydryl formyl, 3- to 8-membered heterocyclyl(thio)carbonyl optionally substituted by a substituent {the ring of the heterocyclyl contains 1 nitrogen atom, oxygen atom or sulfur atom, and may further contain 1 to 2 nitrogen atoms, or may form a 5- to 6-membered spiro ring having 1 to 2 oxygen atoms in the heterocyclyl, the substituent is 1-3 same or different substituents selected from halogen, C1˜C8 alkyl optionally substituted by a substituent (the substituent is one or more same or different substituents selected from halogen and phenyl), C1˜C8 alkylcarbonyl, C1˜C8 alkoxycarbonyl, phenyl optionally substituted by a substituent (the substituent is 1˜3 same or different halogen), nitro, hydroxy, C1˜C8 alkoxy, phenoxy, C1˜C8 alkylsulfanyl, C2˜C8 alkenylsulfanyl, and phenylsulfanyl}, fused 5- to 14-membered bicyclic or tricyclic heterocyclyl(thio)carbonyl optionally substituted by a substituent (the ring of the heterocyclyl contains 1 nitrogen atom, oxygen atom or sulfur atom, and may further contain 1 to 2 nitrogen atoms or oxygen atoms; the substituent is 13 same or different substituents selected from halogen atom and C1˜C8 alkyl), 5- or 6-membered heterocyclyl(thio)carbonyl(thio)carbonyl (the ring of the heterocyclyl contains one nitrogen atom, oxygen atom or sulfur atom, and may further contain one or two nitrogen atoms), C1˜C18 alkoxy(thio)carbonyl, C1˜C18 alkylthio(thio)carbonyl, wherein the C1˜C18 alkoxy(thio)carbonyl or C1˜C18 alkylthio(thio)carbonyl is optionally substituted by a substituent (the substituent is one or more same or different substituents selected from halogen atom, C1˜C8 alkoxy and phenyl), C2˜C8 alkenyloxy(thio)carbonyl, C2˜C8 alkenylsulfanyl(thio)carbonyl, C2˜C8 chain alkynyloxy(thio)carbonyl, C2˜C8 chain alkynylsulfanyl(thio)carbonyl, C3˜C8 cycloalkyloxy(thio)carbonyl, C3˜C8 cycloalkylsulfanyl(thio)carbonyl, phenoxy(thio)carbonyl, phenylsulfanyl(thio)carbonyl, phenyl C1˜C8 alkyloxy(thio)carbonyl, phenyl C1˜C8 alkylthio(thio)carbonyl, wherein the phenoxy(thio)carbonyl, phenylsulfanyl(thio)carbonyl, phenyl C1˜C8 alkyloxy(thio)carbonyl or phenyl C1˜C8 alkylthio(thio)carbonyl is optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from halogen, C1˜C8 alkyl, cyano, C1˜C8 alkylcarbonyl, C1˜C8 alkoxycarbonyl, nitro, and C1˜C8 alkoxy), fused polycyclicoxy(thio)carbonyl, fused polycyclicsulfanyl(thio)carbonyl, a group selected from 5- or 6-membered heterocyclyloxy(thio)carbonyl and 5- or 6-membered heterocyclylsulfanyl(thio)carbonyl, which is optionally substituted by a substituent {the ring of the heterocyclyl contains 1 nitrogen atom, oxygen atom or sulfur atom, and may further contain 1 to 2 nitrogen atoms, the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, phenoxy optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from halogen, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C3˜C8 cycloalkyl, and C1˜C8 alkoxycarbonyl), 2,3-dihydro-1H-indenyloxy, and benzoyl optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from halogen, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C1˜C8 alkoxycarbonyl, nitro, and C1˜C8 alkylsulfonyl)}, amino(thio)formyl optionally substituted by a substituent {the substituent is 1˜3 same or different substituents selected from C1˜C8 alkyl optionally substituted by a substituent (the substituent is one or more same or different substituents selected from halogen, C1˜C8 alkoxycarbonyl, cyano, phenyl, and C1˜C8 alkoxy), C2˜C8 alkenyl, phenyl, C1˜C8 alkylcarbonyl, C1˜C8 alkoxycarbonyl, and C1˜C8 alkoxy},




embedded image


(Het is a 5- to 6-membered heterocyclyl, the heterocyclyl contains, besides C atoms and the 1-N, 0 to 3 atoms or radicals follows to form the ring: O, NRb, C═O, Ra and Rb independently are hydrogen or C1˜C8 alkyl), C1˜C8 alkylsulfoxide, C1˜C8 alkylsulfonyl, C2˜C8 alkenylsulfonyl, C3˜C8 cycloalkylsulfonyl, wherein the C1˜C8 alkylsulfoxide, C1˜C8 alkylsulfonyl, C2˜C8 alkenylsulfonyl, or C3˜C8 cycloalkylsulfonyl is optionally substituted by a substituent (the substituent is one or more same or different substituents selected from halogen and C1˜C8 alkylsulfonyl), phenylsulfonyl, benzylsulfonyl, naphthylsulfonyl, wherein the phenylsulfonyl, benzylsulfonyl, or naphthylsulfonyl is optionally substituted by a substituent [the substituent is 1˜3 same or different substituents selected from halogen, C1˜C8 alkyl, halogenated C1˜C8 alkyl, cyano, C1˜C8 alkylcarbonyl, C1˜C8 alkoxycarbonyl, nitro, C1˜C8 alkoxy, halogenated C1˜C8 alkoxy, C1˜C8 alkylsulfonyl, aminoformyl optionally substituted by a substituent (the substituent is C1˜C8 alkyl), phenoxy optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from halogen, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C3˜C8 cycloalkyl, and C1˜C8 alkoxycarbonyl), C2˜C8 alkenyloxysulfonyl optionally substituted by a substituent {the substituent is 1˜3 same or different substituents selected from C3˜C8 cycloalkyl, cyano, and benzoyl optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from halogen, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C1˜C8 alkoxycarbonyl, nitro, and C1˜C8 alkylsulfonyl)}, C3˜C8 cycloalkenyloxysulfonyl optionally substituted by a substituent {the substituent is 1˜2 same or different substituents selected from oxo, and benzoyl optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from halogen, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C1˜C8 alkoxycarbonyl, nitro, and C1˜C8 alkylsulfonyl)}, and 5- or 6-membered heterocyclyloxysulfonyl optionally substituted by a substituent {the ring of the heterocyclyl contains 1 nitrogen atom, oxygen atom or sulfur atom, and may further contain 1 to 2 nitrogen atoms, the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, phenoxy optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C3˜C8 cycloalkyl, and C1˜C8 alkoxycarbonyl), 2,3-dihydro-1H-indenyloxy, and benzoyl optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C1˜C8 alkoxycarbonyl, nitro, and C1˜C8 alkylsulfonyl)}], 5- to 10-membered heteroarylsulfonyl, 5- to 10-membered heterocyclyloxysulfonyl, wherein the 5- to 10-membered heteroarylsulfonyl or 5- to 10-membered heterocyclyloxysulfonyl is optionally substituted by a substituent {the ring of the heterocyclyl contains 1 nitrogen atom, oxygen atom or sulfur atom, and may further contain 1 to 2 nitrogen atoms, the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, phenoxy optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C3˜C8 cycloalkyl, and C1˜C8 alkoxycarbonyl), 2,3-dihydro-1H-indenyloxy, and benzoyl optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C1˜C8 alkoxycarbonyl, nitro, and C1˜C8 alkylsulfonyl)}, C1˜C8 alkoxysulfonyl, C1˜C8 alkylaminosulfonyl optionally substituted by a substituent (the substituent is one or more same or different substituents selected from halogen atom),




embedded image


(Het is a 5- to 6-membered heterocyclyl, and contains, besides C atoms and the 1-N, 0 to 3 atoms or radicals as follows to form the ring: O, NRb, and C═O, Ra and Rb independently are hydrogen or C1˜C8 alkyl), di(C1˜C8 alkyl)phosphoryl, or di(C1˜C8 alkyl)thiophosphoryl.


In a preferred embodiment, the M group may be C1˜C10 alkyl(thio)carbonyl optionally substituted by a substituent {the substituent is one or more same or different substituents selected from fluorine, chlorine, bromine, C3˜C6 cycloalkyl, C1˜C6 alkoxy, C1˜C6 alkylsulfanyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylcarbonyl, C1˜C6 alkylcarbonyloxy, phenyl, phenylsulfanyl, phenoxy, and benzyloxy, wherein the phenyl, phenylsulfanyl, phenoxy or benzyloxy is optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from fluorine, chlorine, bromine, C1˜C6 alkyl, and C1˜C6 alkoxy)}, C3˜C6 cycloalkyl(thio)carbonyl, C2˜C6 alkenyl(thio)carbonyl optionally substituted by a substituent {the substituent is one or more same or different substituents selected from fluorine, chlorine, bromine, C1˜C6 alkoxy, phenyl, phenylthio, and phenoxy, wherein the phenyl, phenylthio or phenoxy is optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from fluoride, chlorine, bromine, C1˜C6 alkyl, and C1˜C6 alkoxy)}, (thio)benzoyl, (thio)naphthoyl, wherein the (thio)benzoyl or (thio)naphthoyl is optionally substituted by a substituent {the substituent is 1˜3 same or different substituents selected from fluorine, chlorine, bromine, C1˜C6 alkyl, C1˜C6 alkoxy, wherein the C1˜C6 alkyl or C1˜C6 alkoxy is optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from fluorine, chlorine, bromine, and phenyl), cyano, hydroxy, C1˜C6 alkylcarbonyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylcarbonyloxy, C1˜C6 alkylcarbonylamino, amino optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from C1˜C6 alkyl, C1˜C6 alkoxy, C1˜C6 alkylcarbonyl, halogenated C1˜C6 alkyl, and phenyl), phenyl, nitro, and phenoxy}, 3- to 8-membered heterocyclyl(thio)carbonyl optionally substituted by a substituent {the heterocyclyl is




embedded image


the substituent is 1-3 same or different substituents selected from fluorine, chlorine, bromine, C1˜C6 alkyl optionally substituted by a substituent (the substituent is one or more same or different substituents selected from fluorine, chlorine, bromine, and phenyl), C1˜C6 alkylcarbonyl, C1˜C6 alkoxycarbonyl, phenyl optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from fluorine, chlorine, and bromine), nitro, hydroxy, C1˜C6 alkoxy, phenoxy, C1˜C6 alkylsulfanyl, C2˜C6 alkenylsulfanyl, and phenylsulfanyl}, fused 5- to 14-membered bicyclic or tricyclic heterocyclyl(thio)carbonyl optionally substituted by a substituent (the heterocyclyl is




embedded image


embedded image


the substituent is 1˜3 same or different substituents selected from fluorine, chlorine, bromine, and C1˜C6 alkyl), C1˜C10 alkoxy(thio)carbonyl, C1˜C10 alkylsulfanyl(thio)carbonyl, wherein the C1˜C10 alkoxy(thio)carbonyl or C1˜C10 alkylsulfanyl(thio)carbonyl is optionally substituted by a substituent (the substituent is one or more same or different substituents selected from fluorine, chlorine, bromine, C1˜C6 alkoxy, and phenyl), C3˜C6 cycloalkyloxy(thio)carbonyl, C3˜C6 cycloalkylsulfanyl(thio)carbonyl, phenoxy(thio)carbonyl, phenylsulfanyl(thio)carbonyl, phenyl-C1˜C6 alkyloxy(thio)carbonyl, phenyl-C1˜C6 alkylthio(thio)carbonyl, wherein the phenoxy(thio)carbonyl, phenylsulfanyl(thio)carbonyl, phenyl-C1˜C6 alkyloxy(thio)carbonyl or phenyl-C1˜C6 alkylthio(thio)carbonyl is optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from fluorine, chlorine, bromine, C1˜C6 alkyl, cyano, C1˜C6 alkylcarbonyl, C1˜C6 alkoxycarbonyl, nitro, and C1˜C6 alkoxy), amino(thio)formyl optionally substituted by a substituent {the substituent is 1˜3 same or different substituents selected from C1˜C6 alkyl optionally substituted by a substituent (the substituent is one or more same or different substituents selected from fluorine, chlorine, and bromine), C2˜C6 alkenyl, phenyl, C1˜C6 alkylcarbonyl, C1˜C6 alkoxycarbonyl, and C1˜C6 alkoxy)},




embedded image


(Het is



embedded image


Ra and Rb independently are hydrogen or C1˜C6 alkyl), C1˜C6 alkylsulfoxide, C1˜C6 alkylsulfonyl, C2˜C6 alkenylsulfonyl, C3˜C6 cycloalkylsulfonyl, wherein the C1˜C6 alkylsulfoxide, C1˜C6 alkylsulfonyl, C2˜C6 alkenylsulfonyl or C3˜C6 cycloalkylsulfonyl is optionally substituted by a substituent (the substituent is one or more same or different substituents selected from fluorine, chlorine, bromine, and C1˜C6 alkylsulfonyl), phenylsulfonyl, benzylsulfonyl, naphthylsulfonyl, wherein the phenylsulfonyl, benzylsulfonyl or naphthylsulfonyl is optionally substituted by a substituent {the substituent is 1˜3 same or different substituents selected from fluorine, chlorine, bromine, C1˜C6 alkyl, halogenated C1˜C6 alkyl, cyano, C1˜C6 alkanocarbonyl, C1˜C6 alkoxycarbonyl, nitro, C1˜C6 alkoxy, halogenated C1˜C6 alkoxy, C1˜C6 alkylsulfonyl, aminoformyl optionally substituted by a substituent (the substituent is C1˜C6 alkyl), and phenoxy optionally substituted by a substituent (the substituent is 1˜3 same or different substituents selected from fluorine, chlorine, bromine, C1˜C6 alkyl, C1˜C8 halogenated alkyl, C3˜C6 cycloalkyl, and C1˜C6 alkoxycarbonyl)}, 5- to 10-membered heteroarylsulfonyl optionally substituted by a substituent {the heterocyclyl is




embedded image


embedded image


the substituent is 1˜3 same or different substituents selected from fluorine, chlorine, bromine, C1˜C6 alkyl, and phenoxy optionally substituted by a substituent (the substituent is 1-3 same or different substituents selected from fluorine, chlorine, bromine, C1˜C6 alkyl, C1˜C6 halogenated alkyl, C3˜C6 cycloalkyl, and C1˜C6 alkoxycarbonyl)}, C1˜C6 alkylaminosulfonyl optionally substituted by a substituent (the substituent is one or more same or different substituents selected from fluorine, chlorine, and bromine),




embedded image


(Het is



embedded image


Ra and Rb independently are hydrogen or C1˜C6 alkyl), di(C1˜C6 alkyl)phosphoryl, or di(C1˜C6 alkyl)thiophosphoryl.


In a preferred embodiment, M is (thio)formyl, C1˜C18 alkyl(thio)carbonyl, wherein the (thio)formyl or C1˜C18 alkyl (thio)carbonyl is unsubstituted or substituted with a substituent independently selected from the group consisting of: halogen, amino, C3˜C8 cycloalkyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylcarbonyloxy, C1˜C8 alkylcarbonyl, hydroxy(methyl)phosphinyl, and an unsubstituted or halogenated or C1˜C8 alkoxy substituted group selected from phenyl, phenylsulfanyl, phenyloxy, and benzyloxy; an unsubstituted or phenyl substituted group of C1˜C18 alkoxy(thio)carbonyl or C1˜C18 alkylsulfanyl(thio)carbonyl; C3˜C8 cycloalkylsulfanyl(thio)carbonyl; phenyl-C1˜C8 alkylsulfanyl(thio)carbonyl; C2˜C8 alkenyl(thio)carbonyl, wherein the C2˜C8 alkenyl(thio)carbonyl unsubstituted or substituted with a substituent selected from the group consisting of: C1˜C8 alkoxy, phenyl and halogenated phenyl; (thio)benzoyl, wherein the (thio)benzoyl is unsubstituted or substituted with a substituent selected from the group consisting of: halogen, hydroxy, C1˜C8 alkyl, C1˜C8 alkoxy, cyano, halogenated C1˜C8 alkoxy, C1˜C8 alkylcarbonyloxy, C1˜C8 alkylcarbonylamino, amino and amino substituted with 1 or 2 C1˜C8 alkyl; halogenated sulfhydryl formyl; 3- to 8-membered heterocyclyl(thio)carbonyl, wherein the 3- to 8-membered heterocyclyl(thio)carbonyl is unsubstituted or substituted with a substituent selected from C1˜C8 alkyl, halogen, and C1˜C8 alkylsulfanyl; fused 5- to 14-membered bicyclic or tricyclic heterocyclyl(thio)carbonyl; amino(thio)formyl, wherein the amino(thio)formyl is unsubstituted or substituted with a substituent selected from C1˜C8 alkyl and C1˜C8 alkoxy; an unsubstituted or halogen or C1˜C8 alkylsulfonyl substituted group selected from C1˜C8 alkylsulfoxide, C1˜C8 alkylsulfonyl, and C3˜C8 cycloalkylsulfonyl; phenylsulfonyl, benzylsulfonyl or naphthylsulfony 1, wherein each of the phenylsulfonyl, benzylsulfonyl or naphthylsulfonyl is unsubstituted or substituted with a substituent independently selected from the group consisting of: halogen, nitro, C1˜C8 alkyl, halogenated C1˜C8 alkyl, halogenated C1˜C8 alkoxy, C1˜C8 alkylcarbonyl, C1˜C8 alkylsulfonyl, aminoformyl, phenoxy and halogenated phenoxy; 5- to 10-membered heteroarylsulfonyl, wherein the 5- to 10-membered heteroarylsulfonyl is unsubstituted or substituted with C1˜C8 alkyl or phenoxy; C1˜C8 alkylaminosulfonyl that is unsubstituted or substituted with halogen; di(C1˜C8 alkyl)phosphoryl;




embedded image


wherein, Het is selected from




embedded image


Ra and Rb independently are hydrogen or C1˜C6 alkyl.


The oxime derivative refers to a compound having an oxime moiety formed by derivatization of the 4-hydroxy of the pyridazine ring of Formula I. In a preferred embodiment, the oxime group is selected from




embedded image


wherein, R11, R22 separately and independently are hydrogen, C1˜C18 alkyl, C2˜C18 alkenyl, wherein the C1˜C18 alkyl or C2˜C18 alkenyl is optionally substituted with a substituent (the substituent is one or more same or different substituents selected from halogen atom, C1˜C8 alkoxy, C1˜C8 alkylsulfanyl, and C1˜C8 alkylamino), phenyl, phenylcarbonyl, 5- to 6-membered heteroaryl, wherein the phenyl, phenylcarbonyl or 5- to 6-membered heteroaryl is optionally substituted with a substituent (the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C3˜C8 cycloalkyl, C1˜C8 halogenated alkyl, C1˜C8 alkylcarbonyl, C1˜C8 alkoxy, C1˜C8 alkoxycarbonyl, C1˜C8 alkylamino, hydroxy, carboxyl, sulfhydryl, amino, cyano, nitro, and C1˜C8 alkylsulfonyl, the heteroaryl contains at least one oxygen, sulfur, or nitrogen, or other heteroatoms), or R11, R22 form a 5- to 6-membered saturated carbocyclic ring or 5- to 6-membered heterocyclic ring (containing at least one heteroatom such as oxygen, sulfur, nitrogen, etc.).


In a preferred embodiment, R11, R22 independently are hydrogen, C1˜C10 alkyl, C2˜C10 alkenyl, the C1˜C10 alkyl or C2˜C10 alkenyl is optionally substituted with a substituent (the substituent is one or more same or different substituents selected from fluorine, chlorine, bromine, C1˜C6 alkoxy, C1˜C6 alkylsulfanyl, and C1˜C6 alkylamino), phenyl, benzoyl, 5- to 6-membered heteroaryl, wherein the phenyl, benzoyl or 5- to 6-membered heteroaryl is optionally substituted with a substituent (the heteroaryl is




embedded image


the substituent is 1˜3 same or different substituents selected from fluorine, chlorine, bromine, C1˜C6 alkyl, C3˜C6 cycloalkyl, C1˜C6 halogenated alkyl, C1˜C6 alkylcarbonyl, C1˜C6 alkoxy, C1˜C6 alkoxycarbonyl, C1˜C6 alkylamino, hydroxy, carboxyl, sulfhydryl, amino, cyano, nitro, and C1˜C6 alkylsulfonyl), or R11 and R22 form a 5- to 6-membered saturated carbocyclic ring or a 5- to 6-membered heterocyclic ring (containing at least one heteroatom such as oxygen, sulfur, nitrogen, etc.).


In a preferred embodiment, R11 and R22 are independently selected from hydrogen, C1˜C18 alkyl, wherein the C1˜C18 alkyl is unsubstituted or substituted with a substituent selected from C1˜C8 alkoxy, C1˜C8 alkylsulfanyl, and an unsubstituted or halogenated C1˜C8 alkyl substituted group selected from phenyl and 5- to 6-membered heteroaryl; or Rn and R12 forms a 5- to 6-membered saturated carbocyclic ring or a 5- to 6-membered saturated heterocyclic ring.


The hydroxylamine derivative refers to a compound having a hydroxylamine moiety formed by derivatization of the 4-hydroxyl of the pyridazine ring of Formula I. In a preferred embodiment, the hydroxylamine group is selected from




embedded image


wherein, R11′, R22′ are independently hydrogen, C1˜C18 alkyl, C2˜C18 alkenyl, wherein the C1˜C18 alkyl or C2˜C18 alkenyl is optionally substituent with a substituent (the substituent is one or more same or different substituents selected from halogen atom, C1˜C8 alkoxy, C1˜C8 alkylsulfanyl, and C1˜C8 alkylamino), phenyl optionally substituent with a substituent (the substituent is 13 same or different substituents selected from halogen atom, C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C3˜C8 cycloalkyl, C1˜C8 halogenated alkyl, C1˜C8 alkylcarbonyl, C1˜C8 alkoxy, C1˜C8 alkoxycarbonyl, C1˜C8 alkylamino, hydroxy, carboxyl, sulfhydryl, amino, cyano, nitro, and C1˜C8 alkylsulfonyl), C1˜C18 alkoxycarbonyl, or benzoyl optionally substituent with a substituent [the substituent is 13 same or different substituents selected from halogen atom, C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C3˜C8 cycloalkyl, wherein the C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl or C3˜C8 cycloalkyl is optionally substituent with a substituent (the substituent is 13 same or different substituents selected from halogen and phenyl), cyano, C1˜C8 alkylcarbonyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylsulfonyl, C2˜C8 alkenyloxycarbonyl optionally substituent with a substituent {the substituent is 1˜3 same or different substituents selected from C3˜C8 cycloalkyl, cyano, and benzoyl optionally substituent with a substituent (the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C1˜C8 alkoxycarbonyl, nitro, and C1˜C8 alkylsulfonyl)}, C3˜C8 cycloalkenyloxycarbonyl optionally substituent with a substituent {the substituent is 1˜2 same or different substituents selected from oxo, and benzoyl optionally substituent with a substituent (the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C1˜C8 alkoxycarbonyl, nitro, and C1˜C8 alkylsulfonyl)}, hydroxy, carboxyl, sulfhydryl, amino, phenyl, nitro, C1˜C8 alkoxy, C1˜C8 alkylamino, C1˜C8 alkylsulfanyl, wherein the C1˜C8 alkoxy, C1˜C8 alkylamino or C1˜C8 alkylsulfanyl is optionally substituent with a substituent (the substituent is 1˜3 same or different substituents selected from halogen and phenyl), phenoxy, 5- or 6-membered heterocyclyloxycarbonyl optionally substituent with a substituent {the ring of the heterocyclyl contains one nitrogen atom, oxygen atom or sulfur atom, may further contain 1 to 2 nitrogen atoms; the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, phenoxy optionally substituent with a substituent (the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C3˜C8 cycloalkyl, and C1˜C8 alkoxycarbonyl), 2,3-dihydro-1H-indenyloxy, and benzoyl optionally substituent with a substituent (the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C1˜C8 alkoxycarbonyl, nitro, and C1˜C8 alkylsulfonyl)}, and 5- or 6-membered heterocyclyloxysulfonyl optionally substituent with a substituent {the ring in the heterocyclyl contains one nitrogen atom, oxygen atom or sulfur atom, and may further contain 1 or 2 nitrogen atoms; the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, phenoxy optionally substituent with a substituent (the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C3˜C8 cycloalkyl, and C1˜C8 alkoxycarbonyl), 2,3-dihydro-1H-indenyloxyl, and benzoyl optionally substituent with a substituent (the substituent is 1˜3 same or different substitutions selected from halogen atom, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C1˜C8 alkoxycarbonyl, nitro, and C1˜C8 alkylsulfonyl)}].


In a preferred embodiment, R11′, R22′ are independently hydrogen, C1˜C10 alkyl, C2˜C10 alkenyl, wherein the C1˜C10 alkyl or C2˜C10 alkenyl is optionally substituent with a substituent (the substituent is one or more same or different substituents selected from fluorine, chlorine, bromine), C1˜C10 alkoxycarbonyl, phenyl, or benzoyl, wherein the phenyl or benzoyl optionally substituent with a substituent (the substituent is 1˜3 same or different substituents selected from fluorine, chlorine, bromine, C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, C1˜C6 halogenated alkyl, C1˜C6 alkylcarbonyl, C1˜C6 alkoxy, C1˜C6 alkoxycarbonyl, C1˜C6 alkylamino, hydroxy, carboxyl, sulfhydryl, amino, cyano, nitro, and C1˜C6 alkylsulfonyl).


In a preferred embodiment, R11′ and R22′ independently is C1˜C18 alkyl.


The ether derivative refers to a compound formed by bonding the oxygen atom of the 4-hydroxy of the pyridazine ring with a group as follows: cyano, C1˜C18 alkyl, C2˜C18 alkenyl, wherein the C1˜C18 alkyl or C2˜C18 alkenyl is optionally substituted with a substituent (the substituent is one or more same or different substituents selected from halogen atom, C1˜C8 alkoxy, C1˜C8 alkylsulfanyl, C1˜C8 alkylamino, di(C1˜C8 alkyl)amino, C1˜C8 alkoxycarbonyl, C1˜C8 alkoxycarbonyloxy, C3˜C8 cycloalkyloxy, C3˜C8 cycloalkylsulfanyl, C3˜C8 cycloalkylamino, di(C3˜C8cycloalkyl)amino, C3˜C8 cycloalkoxycarbonyl, and C3˜C8 cycloalkoxycarbonyloxy), phenyl, benzyl, or benzoyl-C1˜C8 alkyl, wherein the phenyl, benzyl or benzoyl-C1˜C8 alkyl is optionally substituent with a substituent [the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C3˜C8 cycloalkyl, wherein the C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl or C3˜C8 cycloalkyl is optionally substituent with a substituent (the substituent is 1˜3 same or different substituents selected from halogen and phenyl), cyano, C1˜C8 alkylcarbonyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylsulfonyl, C2˜C8 alkenyloxycarbonyl optionally substituent with a substituent {the substituent is 1˜3 same or different substituents selected from C3˜C8 cycloalkyl, cyano, and benzoyl optionally substituent with a substituent (the substituent is 1˜3 same or different substitutions selected from halogen atom, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C1˜C8 alkoxycarbonyl, nitro, and C1˜C8 alkylsulfonyl)}, C3˜C8 cycloalkenyloxycarbonyl optionally substituent with a substituent {the substituent is 1˜2 same or different substituents selected from oxo, and benzoyl optionally substituent with a substituent (the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C1˜C8 alkoxycarbonyl, nitro, and C1˜C8 alkylsulfonyl)}, hydroxy, carboxyl, sulfhydryl, amino, phenyl, nitro, C1˜C8 alkoxy, C1˜C8 alkylamino, C1˜C8 alkylsulfanyl, wherein the C1˜C8 alkoxy, C1˜C8 alkylamino or C1˜C8 alkylsulfanyl is optionally substituent with a substituent (the substituent is 1˜3 same or different substituents selected from halogen and phenyl), phenoxy, 5- or 6-membered heterocyclyloxycarbonyl optionally substituent with a substituent {the ring of the heterocyclyl contains one nitrogen atom, oxygen atom or sulfur atom, and may further contain 1 to 2 nitrogen atoms; the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, phenoxy optionally substituent with a substituent (the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C3˜C8 cycloalkyl, and C1˜C8 alkoxycarbonyl), 2,3-dihydro-1H-indenyloxy, and benzoyl optionally substituent with a substituent (the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C1˜C8 alkoxycarbonyl, nitro, and C1˜C8 alkylsulfonyl)}, and 5- or 6-membered heterocyclyloxysulfonyl optionally substituent with a substituent {the ring of the heterocyclyl contains one nitrogen atom, oxygen atom or sulfur atom, and may further contain 1 to 2 nitrogen atoms; the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, phenoxy optionally substituent with a substituent (the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C3˜C8 cycloalkyl, and C1˜C8 alkoxycarbonyl), 2,3-dihydro-1H-indenyloxy, and benzoyl optionally substituent with a substituent (the substituent is 1˜3 same or different substituents selected from halogen atom, C1˜C8 alkyl, C1˜C8 halogenated alkyl, C1˜C8 alkoxycarbonyl, nitro, and C1˜C8 alkylsulfonyl)}]; wherein, in Formula I-1, when X is —CF3 and A is phenyl in Formula I-1, the M group is not methyl or allyl; when X is —CHFCF3 and A is —CHFCF3, the M group is not




embedded image


In a preferred embodiment, the ether derivative refers to a compound formed by bonding the oxygen of the 4-hydroxy of the pyridazine ring with a group as follows: C8˜C18 alkyl, C8˜C18 alkenyl, C1˜C10 alkyl, C2˜C10 alkenyl, wherein the C1˜C10 alkyl or C2˜C10 alkenyl is substituent with a substituent {the substituent is one or more same or different substituents selected from fluorine, chlorine, bromine, C1˜C6 alkoxy, C1˜C6 alkylsulfanyl, C1˜C6 alkylamino, C1˜C6 alkoxycarbonyl, C1˜C6 alkoxycarbonyloxy, and C3˜C6 cycloalkoxycarbonyloxy}, phenyl, benzyl, or benzoyl-C1˜C6 alkyl, wherein the phenyl, benzyl or benzoyl-C1˜C6 alkyl is optionally substituent with a substituent (the substituent is 1˜3 same or different substituents selected from fluorine, chlorine, bromine, C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, C1˜C6 halogenated alkyl, C1˜C6 alkylcarbonyl, C1˜C6 alkoxy, C1˜C6 alkoxycarbonyl, C1˜C6 alkylamino, hydroxy, carboxyl, sulfhydryl, amino, cyano, nitro, and C1˜C6 alkylsulfonyl).


In a preferred embodiment, the group is selected from C1˜18 alkyl, which is unsubstituted or substituted with a substituent selected from C1˜C8 alkoxycarbonyl and C1˜C8 alkoxycarbonyloxy; and phenyl, benzyl or benzoyl-C1˜C8 alkyl, each of which is unsubstituted or substituted with a substituent selected from halogen and C1˜C8 alkoxy.


A method for preparing the pyridazinol compound, comprising the steps of:


(1) subjecting a compound of Formula II and a compound of Formula III to Suzuki reaction to obtain a compound of Formula IV;


(2) hydrolyzing the compound of Formula IV to obtain a compound of Formula I;


wherein the reaction route is as follows:




embedded image


or comprising:


(a) hydrolyzing a compound of Formula II to give a compound of Formula V;


(b) subjecting the compound of Formula V and a compound of Formula III to Suzuki reaction to obtain a compound of Formula I;


the reaction route is as follows:




embedded image


L is halogen, preferably bromine, other groups are as defined above.


In a preferred embodiment, each of the steps independently is carried out in the range of 20 to 150° C., preferably 50 to 130° C.;


steps (1) and (b) are carried out in the presence of a catalyst, a base and a solvent, wherein the catalyst is Pd(dppf)Cl2CH2Cl2, Pd(dba)2, Pd2(dba)3, Pd(PPh3)4, PdCl2, Pd(OAc)2, Pd(dppf)Cl2, Pd(PPh3)2Cl2, or Ni(dppf)Cl2, the base is one or more selected from Et3N, NaHCO3, KOAc, K2CO3, K3PO4, Na2CO3, CsF, Cs2CO3, t-BuONa, EtONa, KOH, and NaOH, the solvent is THF/water, toluene/water, DMF/water, 1,4-dioxane/water, toluene/ethanol/water, acetonitrile/water, THF, toluene, 1,4-dioxane, acetonitrile, or DMF system;


steps (2) and (a) are carried out in the presence of a base and a solvent or in the presence of a solution of boron tribromide, a solution of hydrobromic acid in acetic acid, a solution of hydrochloric acid in methanol or a solution of hydrochloric acid in ethyl acetate, the base is preferably selected from NaOH, KOH, potassium acetate, and sodium acetate, the solvent is preferably water or DMSO.


When the derivative is an ester or ether derivative, the reaction route is as follows:




embedded image


wherein, Y1 is a halogen, preferably chlorine or bromine; other groups are as defined above.


When the derivative is an oxime or hydroxylamine derivative, the reaction route is as follows:




embedded image


wherein, Y2 is a halogen, preferably chlorine or fluorine; other groups are as defined above.


In a preferred embodiment, reactions for preparing the ester and ether derivatives and the second step for preparing the oxime and hydroxylamine derivatives are carried out in the presence of a base and a solvent, the base is one or more selected from the group consisting of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, cesium carbonate, triethylamine and diisopropylethylamine; the solvent is THF, 1,4-dioxane, toluene, 1,2-dichloroethane, ethyl acetate, acetonitrile, DMF, acetone, dichloromethane, or chloroform.


In a preferred embodiment, the first step for preparing the oxime and hydroxylamine derivative is carried out in the presence of a halogenation reagent and a solvent, wherein the halogenation reagent is Phenofluor/cesium fluoride or POCl3, and the solvent is one or more selected from the group consisting of toluene, 1,2-dichloroethane, and DMF; the reaction temperature is in the range of 0 to 120° C., preferably 20 to 80° C.


Unless otherwise stated, the terms used in the text have the meanings commonly understood by those skilled in the art. When the terms used are different from those commonly understood in the art, the definitions herein prevail.


In the definitions of the compounds represented by the above formulas, and in all the aftermentioned compounds, the term “alkyl” or “—(CH2)n—” for the definition of a corresponding radical having more than two carbon atoms, whether used alone or in a compound word, may be a straight or branched chain. For example, alkyl in the compound word “heteroarylalkyl” and —(CH2)n— in “R—O—(CH2)n—” all may be straight or branched. In a preferred embodiment, —(CH2)n— may be —CH2—, —CH2CH2—, —CH(CH3)—, —C(CH3)2—, and the like.


The alkyl is, for example, methyl; ethyl; n-propyl or isopropyl; n-butyl, isobutyl, tert-butyl or 2-butyl; pentyl; hexyl, for example, n-hexyl, isohexyl or 1,3-dimethylbutyl. Similarly, alkenyl is, for example, allyl, 1-methyl-allyl, 2-methyl-allyl, but-2-enyl, but-3-enyl, 1-methyl-but-3-enyl or 1-methyl-but-2-enyl. Alkynyl is, for example, propargyl, but-2-ynyl, but-3-ynyl, or 1-methyl-but-3-ynyl. Multiple bonds can be at any site of an unsaturated group. Cycloalkyl preferably is a saturated carbocyclic ring having 3 to 8 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, cycloalkenyl preferably is a monocyclic ring having 3 to 8 carbocyclic ring members and at least one carbon-carbon double bond, such as cyclopropenyl, cyclobutenyl, cyclopentenyl or cyclohexenyl, wherein the double bond may be at any site of the ring. Halogen is fluorine, chlorine, bromine or iodine.


Unless specifically limited, heterocyclyl includes aliphatic heterocyclyl and heteroaryl.


If a group is substituted by a substituent, it should be understood that the group is substituted by one or more same or different substituents selected from those mentioned. In addition, the identical or different variables in identical or different substituents should be independently selected, i.e., could be same or different. This also applicable to a 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, a group 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




embedded image


is substituted with one methyl, it can be




embedded image


etc.


The compound of the present invention may exist in the form of one or more stereoisomers. The various isomers include enantiomers, diastereomers, and geometric isomers. These isomers and mixtures thereof are all within the scope of the invention. A herbicidal composition, comprising component (i) the pyridazinol compound of Formula I or the derivative thereof as shown in Formula I-1.


Preferably, further comprises component (ii) one or more additional herbicides and/or safeners.


More preferably, also comprises component (iii) an agriculturally acceptable formulation auxiliary.


Usable combination partners for the inventive compounds in mixture formulations or in a tankmix are, for example, known active ingredients based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthase, p-hydroxyphenylpyruvate dioxygenase, phytoendesaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as described, for example, in Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 15th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2009 and literature cited therein. Examples of known herbicides or plant growth regulators which can be combined with the inventive compounds include the active ingredients which follow (the compounds are designated by the common name according to the International Organization for Standardization (ISO) or by the chemical name or by the code number) and always encompass all use forms, such as acids, salts, esters and isomers, such as stereoisomers and optical isomers. In this list, one or else, in some cases, more than one application forms is mentioned:


Acetochlor, Acibenzolar, Acibenzolar-S-methyl, Acifluorfen, Acifluorfen-sodium, Aclonifen, Alachlor, Allidochlor, Alloxydim, Alloxydim-sodium, Ametryn, Amicarbazone, Amidochlor, Amidosulfuron, Aminocyclopyrachlor, Aminopyralid, Amitrole, Ammoniumsulfamat, Ancymidol, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Aziprotryn, Beflubutamid, Benazolin, Benazolin-ethyl, Bencarbazone, Benfluralin, Benfuresate, Bensulide, Bensulfuron, Bensulfuron-methyl, Bentazone, Benzfendizone, Benzobicyclon, Benzofenap, Benzofluor, Benzoylprop, Bicyclopyrone, Bifenox, Bilanafos, Bilanafos-natrium, Bispyribac, Bispyribac-natrium, Bromacil, Bromobutide, Bromofenoxim, Bromoxynil, Bromuron, Buminafos, Busoxinone, Butachlor, Butafenacil, Butamifos, Butenachlor, Butralin, Butroxydim, Butylate, Cafenstrole, Carbetamide, Carfentrazone, Carfentrazone-ethyl, Chlomethoxyfen, Chloramben, Chlorazifop, Chlorazifop-butyl, Chlorbromuron, Chlorbufam, Chlorfenac, Chlorfenac-natrium, Chlorfenprop, Chlorflurenol, Chlorflurenol-methyl, Chloridazon, Chlorimuron (acid), Chlorimuron-ethyl, Chlormequat-chloride, Chlomitrofen, Chlorophthalim, Chlorthal-dimethyl, Chlorotoluron, Chlorsulfuron, Cinidon, Cinidon-ethyl, Cinmethylin, Cinosulfuron, Clethodim, Clodinafop, Clodinafop-propargyl, Clofencet, Clomazone, Clomeprop, Cloprop, Clopyralid, Cloransulam, Cloransulam-methyl, Cumyluron, Cyanamide, Cyanazine, Cyclanilide, Cycloate, Cyclosulfamuron, Cycloxydim, Cycluron, Cyhalofop, Cyhalofop-butyl, Cyperquat, Cyprazine, Cyprazole, 2,4-D, 2,4-DB, Daimuron/dymron, Dalapon, Daminozide, Dazomet, n-decanol, Desmedipham, Desmetryn, Detosyl-Pyrazolate (DTP), Diallate, Dicamba, Dichlobenil, Dichlorprop, Dichlorprop-P, Diclofop, Diclofop-methyl, Diclofop-P-methyl, Diclosulam, Acetyl Alachlor acid (Diethatyl), Acetyl Alachlor (Diethatyl-ethyl), Difenoxuron, Difenzoquat, Diflufenican, Diflufenzopyr, Diflufenzopyr-natrium, Dimefuron, Dikegulac-sodium, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimethenamid-P, Dimethipin, Dimetrasulfuron, Dinitramine, Dinoseb, Dinoterb, Diphenamid, Dipropetryn, Diquat, Diquat dibromide, Dithiopyr, Diuron, DNOC, Eglinazine-ethyl, Endothal, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron, Ethametsulfuron-methyl, Ethephon, Ethidimuron, Ethiozin, Ethofumesate, Ethoxyfen, Ethoxyfen-ethyl, Ethoxysulfuron, Etobenzanid, F-5331, i.e., N—[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]ethylsulfonamide, F-7967, i.e., 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl) pyrimidine-2,4(1H,3H)-dione, Fenoprop, Fenoxaprop, Fenoxaprop-P, Fenoxaprop-ethyl, Fenoxaprop-P-ethyl, Fenoxasulfone, Fentrazamide, Fenuron, Flamprop, Flamprop-M-isopropyl, Flamprop-M-methyl, Flazasulfuron, Florasulam, Fluazifop, Fluazifop-P, Fluazifop-butyl, Fluazifop-P-butyl, Fluazolate, Flucarbazone, Flucarbazone-sodium, Flucetosulfuron, Fluchloralin, Flufenacet(Thiafluamide)), Flufenpyr, Flufenpyr-ethyl, Flumetralin, Flumetsulam, Flumiclorac, Flumiclorac-pentyl, Flumioxazin, Flumipropyn, Fluometuron, Fluorodifen, Fluoroglycofen, Fluoroglycofen-ethyl, Flupoxam, Flupropacil, Flupropanate, Flupyrsulfuron, Flupyrsulfuron-methyl-sodium, Flurenol, Flurenol-butyl, Fluridone, Flurochloridone, Fluroxypyr, Fluroxypyr-meptyl, Flurprimidol, Flurtamone, Fluthiacet, Fluthiacet-methyl, Fluthiamide, Fomesafen, Foramsulfuron, Forchlorfenuron, Fosamine, Furyloxyfen, Gibberellinsäure, Glufosinate, Glufosinate-ammonium, Glufosinate-P, Glufosinate-P-ammonium, Glufosinate-P-natrium, Glyphosate, Glyphosate-isopropylammonium, H-9201, i.e., 0-(2,4-dimethyl-6-nitrophenyl)-O-ethyl-isopropylthiophosphoramide, Halosafen, Halosulfuron, Halosulfuron-methyl, Haloxyfop, Haloxyfop-P, Haloxyfop-ethoxyethyl, Haloxyfop-P-ethoxyethyl, Haloxyfop-methyl, Haloxyfop-P-methyl, Hexazinone, HW-02, i.e., 1-(dimethyloxyphosphoryl)ethyl (2,4-dichlorophenoxy) acetate, Imazamethabenz, Imazamethabenz-methyl, Imazamox, Imazamox-ammonium, Imazapic, Imazapyr, imazapyr-isopropylammonium, Imazaquin, Imazaquin-ammonium, Imazethapyr, Imazethapyr-ammonium, Imazosulfuron, Inabenfide, Indanofan, Indaziflam, Indoleacetic acid (IAA), 4-indol-3-ylbutyric acid (IB A), Iodosulfuron, Iodosulfuron-methyl-natrium, Ioxynil, Ipfencarbazone, Isocarbamid, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, KUH-043, i.e., 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, Karbutilate, Ketospiradox, Lactofen, Lenacil, Linuron, Maleinsäure-hydrazid, MCPA, MCPB, MCPAB-methyl, -ethyl and -sodium salt, 2-methyl-4-chlorophenoxypropionic acid (Mecoprop), sodium 2-methyl-4-chlorophenoxypropionate, butyloxyethyl 2-methyl-4-chlorophenoxypropionate (Mecoprop-butotyl), Mecoprop-P-butotyl, Mecoprop-P-dimethylammonium, Mecoprop-P-2-ethylhexyl, Mecoprop-P-kalium, Mefenacet, Mefluidide, Mepiquatchlorid, Mesosulfuron, Mesosulfuron-methyl, Mesotrione, Methabenzthiazuron, Metam, Metamifop, Metamitron, Metazachlor, Metazosulfuron, Methazole, Methiopyrsulfuron, Methiozolin, Methoxyphenone, Methyldymron, 1-methylcyclopropene, methyl isothiocyanate, Metobenzuron, Metobromuron, Metolachlor, S-Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron, Metsulfuron-methyl, Molinate, Monalide, Monocarbamide, Monocarbamide-dihydrogensulfat, Monolinuron, Monosulfuron, Monosulfuron-ester, Monuron, MT-128, i.e., 6-chloro-N-[(2E)-3-chloroprop-2-en-1-yl]-5-methyl-N-phenylpyridazin-3-amine, MT-5950, i.e., N—[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, Naproanilide, Napropamide, Naptalam, NC-310, i.e., 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, Neburon, Nicosulfuron, Nipyraclofen, Nitralin, Nitrofen, Nitrophenolate-natrium (mixture of isomers), Nitrofluorfen, nonylic acid, Norflurazon, Orbencarb, Orthosulfamuron, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Paclobutrazol, Paraquat, Paraquat dichloride, n-nonylic acid (Pelargonsaure), Pendimethalin, Pendralin, Penoxsulam, Pentanochlor, Pentoxazone, Perfluidone, Pethoxamid, Phenisopham, Phenmedipham, Phenmedipham-ethyl, Picloram, Picolinafen, Pinoxaden, Piperophos, Pirifenop, Pirifenop-butyl, Pretilachlor, Primisulfuron, Primisulfuron-methyl, Probenazole, Profluazol, Procyazine, Prodiamine, Prifluraline, Profoxydim, Prohexadione, Prohexadione-calcium, Prohydroj asmone, Prometon, Prometryn, Propachlor, Propanil, Propaquizafop, Propazine, Propham, Propisochlor, Propoxycarbazone, Propoxycarbazone-natrium, Propyrisulfuron, Propyzamide, Prosulfalin, Prosulfocarb, Prosulfuron, Prynachlor, Pyraclonil, Pyraflufen, Pyraflufen-ethyl, Pyrasulfotole, Pyrazolynate (Pyrazolate), Pyrazosulfuron, Pyrazosulfuron-ethyl, Pyrazoxyfen, Pyribambenz, Pyribambenz-isopropyl, Pyribambenz-propyl, Pyribenzoxim, Pyributicarb, Pyridafol, Pyridate, Pyriferalid, Pyriminobac, Pyriminobac-methyl, Pyrimisulfan, Pyrithiobac, Pyrithiobac-natrium, Pyroxasulfone, Pyroxsulam, Quinclorac, Quinmerac, Quinoclamine, Quizalofop, Quizalofop-ethyl, Quizalofop-P, Quizalofop-P-ethyl, Quizalofop-P-tefuryl, Rimsulfuron, Saflufenacil, Secbumeton, Sethoxydim, Siduron, Simazine, Simetryn, SN-106279, i.e., methyl-(2R)-2-{7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-naphthyl}oxy)propionate, Sulcotrione, Sulfallate(CDEC), Sulfentrazone, Sulfometuron, Sulfometuron-methyl, Sulfosate(Glyphosate-trimesium), Sulfosulfuron, SYN-523, SYP-249, i.e., 1-ethyloxy-3-methyl-1-oxobut-3-en-2-yl-5-[2-chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoic acid ester, SYP-300, i.e., l-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazine-6-yl]-3-propyl-2-thioimidazolidine-4,5-dione, Tebutam, Tebuthiuron, Tecnazene, Tefuryltrione, Tembotrione, Tepraloxydim, Terbacil, Terbucarb, Terbuchlor, Terbumeton, Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thiazafluron, Thiazopyr, Thidiazimin, Thidiazuron, Thiencarbazone, Thiencarbazone-methyl, Thifensulfuron, Thifensulfuron-methyl, Thiobencarb, Tiocarbazil, Topramezone, Tralkoxydim, Triafamone, Triallate, Triasulfuron, Triaziflam, Triazofenamide, Tribenuron, Tribenuron-methyl, trichloroacetic acid (TCA), Triclopyr, Tridiphane, Trietazine, Trifloxysulfuron, Trifloxysulfuron-natrium, Trifluralin, Triflusulfuron, Triflusulfuron-methyl, Trimeturon, Trinexapac, Trinexapac-ethyl, Tritosulfuron, Tsitodef, Uniconazole, Uniconazole-P, Vemolate, ZJ-0862, i.e., 3,4-dichloro-N-{2-[(4,6-dimethoxy-pyrimidin-2-yl)oxy]benzyl}aniline, and the following compounds:




embedded image


The additional herbicide is one selected from a HPPD inhibitor, a hormones and a PDS inhibitor; preferably, the HPPD inhibitor is selected from the group consisting of Sulcotrione (CAS NO.: 99105-77-8), Mesotrione (CAS NO.: 104206-82-8), Topramezone (CAS NO.: 210631-68-8), Tembotrione (CAS NO.: 335104-84-2), Bicyclopyrone (CAS NO.: 352010-68-5), Tefuryltrione (CAS NO.: 473278-76-1), Benzobicyclon (CAS NO.: 156963-66-5), Lancotrione (CAS NO.: 1486617-21-3), Shuangzuocaotong (CAS NO.: 1622908-18-2), Huanbifucaotong (CAS NO.: 1855929-45-1), Sanzuohuangcaotong (CAS NO.: 1911613-97-2), Benzuofucaotong (CAS NO.: 1992017-55-6), Pyrasulfotole (CAS NO.: 365400-11-9), Pyrazolate (CAS NO.: 58011-68-0), Benzofenap (CAS NO.: 82692-44-2), Tolpyralate (CAS NO.: 1101132-67-5), Fenquinotrione (CAS NO.: 1342891-70-6), and Isoxaflutole (CAS NO.: 141112-29-0); the hormone is selected from the group consisting of Fluroxypyr (CAS NO.: 69377-81-7) or a derivative thereof, Halauxifen-methyl (CAS NO.: 943831-98-9), Florpyrauxifen-benzyl (CAS NO.: 1390661-72-9), Quinclorac (CAS NO.: 84087-01-4), Quinmerac (CAS NO.: 90717-03-6), Chipton (CAS NO.: 94-74-6), 2-methyl-4-chlorophenoxypropionic acid (CAS NO.: 93-65-2), MCPB (CAS NO.: 94-81-5), 2,4-D (CAS NO.: 94-75-7), Dichlorprop (CAS NO.: 120-36-5), 2,4-DB (CAS NO.: 94-82-6), Dicamba (CAS NO.: 1918-00-9), Picloram (CAS NO.: 1918-02-1), Trichlopyr (CAS NO.: 55335-06-3), Clopyralid (CAS NO.: 1702-17-6), and Triclopyr (CAS NO.: 55335-06-3) and derivatives thereof, the PDS inhibitor is selected from the group consisting of Flurochloridone (CAS NO.: 61213-25-0), Flurtamone (CAS NO.: 96525-23-4), Diflufenican (CAS NO.: 83164-33-4), Picolinafen (CAS NO.: 137641-05-5), Beflubutamid (CAS NO.: 113614-08-7), Norflurazon (CAS NO.: 27314-13-2), and Fluridone (CAS NO.: 59756-60-4).


wherein, the Fluroxypyr derivative include, but are not limited to: Fluroxypyr-mepthyl; the derivatives of Chipton, 2-methyl 4-chlorophenoxypropionic acid, MCPB include but are not limited to: sodium salts, potassium salts, dimethylammonium salts, isopropylamine salts, etc., and methyl esters, ethyl esters, isooctyl esters, ethylthio esters, etc.; the derivatives of 2,4-D, Dichlorprop and 2,4-DB include but are not limited to: salts such as sodium salts, potassium salts, dimethylammonium salts, triethanolammonium salts, isopropylamine salts, cholines, etc., and esters such as methyl esters, ethyl esters, butyl esters, isooctyl esters, etc.


In a preferred embodiment, the component (i) is




embedded image


In a preferred embodiment, the additional herbicide is one or more selected from the group consisting of Sulcotrione, Mesotrione, Topramezone, Tembotrione, Bicyclopyrone, Tefuryltrione, Benzobicyclon, Lancotrione, Shuangzuocaotong, Huanbifucaotong, Sanzuohuangcaotong, Benzuofucaotong, Pyrasulfotole, Benzofenap, Tolpyralate, Isoxaflutole, Fluroxypyr or esters thereof, Halauxifen-methyl, Florpyrauxifen-benzyl, Quinclorac, Chipton or salts/esters thereof, 2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, MCPB or salts/esters thereof, 2,4-D or salts/esters thereof, Dichlorprop or salts/esters thereof, 2,4-DB or salts/esters thereof, Dicamba, Picloram, Trichlopyr, Clopyralid, Triclopyr, Flurochloridone, Flurtamone, Diflufenican, Picolinafen, Beflubutamid, Norflurazon and Fluridone.


A method for controlling a harmful plant, comprising applying a herbicidally effective amount of at least one of the above mentioned pyridazinol compound or derivative thereof, or the herbicidal composition to the harmful plant or an area with the harmful plant.


Use of the above mentioned pyridazinol compound or derivative thereof, or the herbicidal composition for controlling a harmful plant;


Preferably, the pyridazinol compound or derivative thereof or the herbicidal composition is used to control a harmful plant in a useful crop.


More preferably, the useful crop is a genetically modified crop or a crop treated by genome editing technique. In a preferred embodiment, the useful crop is selected from the group consisting of wheat, corn, rice, soybean, cotton, rape, millet and sorghum.


The compounds of 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, Folium, Alopecums, Phalaris, Echinochloa, Digitaria, Setaria and also Cypems 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 Cypems. 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.


In a preferred embodiment, the compounds described herein exhibit excellent inhibitory activity against the following harmful plants: Amaranthus retroflexus, Rorippa indica, Veronica polita, Chenopodiaceae, Echinochloa crus-galli, Setaria viridis, Galium aparine, Abutilon mill, Sisymbrium sophia and Galinsoga parviflora.


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, cotton 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 Formula I according to the invention or their salts 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 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-A 0 221 044, EP-A 0 131 624). For example, there have been described several cases:

    • 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, for example, glufosinate (EP-A 0 242 236, EP-A 0 242 246), glyphosate-type (WO 92/00377), or sulfonylurea-type (EP-A 0 257 993, U.S. Pat. No. 5,013,659);
    • transgenic crop plants, for example cotton, 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 constmcted ribozyme which specifically cleaves transcripts of the abovementioned 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 Formula I. The compounds of 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- 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-Kuhler, “Chemische Technologic” [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. Mars den, “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, “Grenzflchenaktive thylenoxidaddukte” [Surface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Kuchler, “Chemische Technologic” [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 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 Formula I. 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.


For use, 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 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/ha or more of active substance, but it is preferably between 0.005 and 750 g/ha, in particular between 0.005 and 250 g/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, variety and biological activity of a compound, we preferably synthesized several compounds, part of which are listed in the following table 1-2. The structure and information of a certain compound are shown in Table 1-2. The compounds in Table 1-2 are listed for further explication of the present invention, other than any limit therefor. The subject of the present invention should not be interpreted by those skilled in the art as being limited to the following compounds.









TABLE 1







Structure and 1HNMR data of Compound I









I









embedded image















No.
X
A

1H NMR














1
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.55-7.47 (m, 2H), 7.41-7.27 (m, 3H), 7.06 (s, 1H), 5.58 (s, 1H).





2
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.46-7.40 (m, 1H), 7.39-7.30 (m, 2H), 7.32- 7.26 (m, 1H), 7.03 (s, 1H), 5.68 (s, 1H), 2.50 (s, 3H).





3
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.45-7.41 (m, 1H), 7.40-7.30 (m, 2H), 7.29- 7.23 (m, 1H), 7.06 (s, 1H), 5.58 (s, 1H), 2.50 (s, 3H).





4
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.44 (d, J = 7.5 Hz, 2H), 7.22 (d, J = 7.5 Hz, 2H), 7.06 (s, 1H), 5.57 (s, 1H), 2.33 (s, 3H).





5
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.47-7.44 (m, 1H), 7.43-7.34 (m, 2H), 7.34- 7.27 (m, 1H), 7.06 (s, 1H), 5.60 (s, 1H), 2.61 (q, J = 8.0 Hz, 2H), 1.21 (t, J = 8.0 Hz, 3H).





6
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.46 (d, J = 7.5 Hz, 2H), 7.11 (d, J = 7.5 Hz, 2H), 7.06 (s, 1H), 5.57 (s, 1H), 2.67 (q, J = 8.0 Hz, 2H), 1.19 (t, J = 8.0 Hz, 3H).





7
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.50-7.42 (m, 1H), 7.45-7.34 (m, 3H), 7.01 (s, 1H), 5.60 (s, 1H), 2.66 (q, J = 8.0, Hz, 2H), 1.20 (t, J = 8.0 Hz, 3H).





8
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.56 (d, J = 7.5 Hz, 2H), 7.43 (d, J = 7.5 Hz, 2H), 7.00 (s, 1H), 5.77 (s, 1H), 2.94 (hept, J = 8.0 Hz, 1H), 1.20 (d, J = 8.0 Hz, 6H).





9
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.55-7.50 (m, 1H), 7.45-7.33 (m, 3H), 7.06 (s, 1H), 5.61 (s, 1H), 2.90 (hept, J = 8.0 Hz, 1H), 1.24 (d, J = 8.0 Hz, 6H).





10
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.50-7.40 (m, 2H), 7.37-7.30 (m, 2H), 7.01 (s, 1H), 5.58 (s, 1H), 3.12 (hept, J = 8.0 Hz, 1H), 1.27 (d, J = 8.0 Hz, 6H).





11
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.56 (d, J = 7.5 Hz, 2H), 7.43 (d, J = 7.5 Hz, 2H), 7.00 (s, 1H), 5.77 (s, 1H), 2.61-2.46 (m, 1H), 1.80-1.61 (m, 2H), 1.16 (d, J = 7.0 Hz, 3H), 0.76 (t, J = 8.0 Hz, 3H).





12
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.57-7.39 (m, 2H), 7.42-7.33 (m, 2H), 7.06 (s, 1H), 5.58 (s, 1H), 2.65-2.49 (m, 1H), 1.84-1.65 (m, 2H), 1.18 (d, J = 7.0 Hz, 3H), 0.79 (t, J = 8.0 Hz, 3H).





13
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.50-7.35 (m, 4H), 7.04 (s, 1H), 5.67 (s, 1H), 2.79-2.68 (m, 1H), 1.94-1.75 (m, 2H), 1.28 (d, J = 7.0 Hz, 3H), 0.83 (t, J = 8.0 Hz, 3H).





14
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.46 (d, J = 7.5 Hz, 2H), 7.12 (d, J = 7.5 Hz, 2H), 7.06 (s, 1H), 5.56 (s, 1H), 2.59 (t, J = 7.5 Hz, 2H), 1.56-1.32 (m, 4H), 0.89 (t, J = 8.0 Hz, 3H).





15
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.47-7.33 (m, 3H), 7.34-7.28 (m, 1H), 7.06 (s, 1H), 5.59 (s, 1H), 2.61 (t, J = 7.5 Hz, 2H), 1.59-1.37 (m, 4H), 0.95 (t, J = 8.0 Hz, 3H).





16
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.49-7.37 (m, 4H), 7.01 (s, 1H), 5.62 (s, 1H), 2.58 (t, J = 7.5 Hz, 2H), 1.53-1.33 (m, 4H), 0.85 (t, J = 8.0 Hz, 3H).





17
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.54 (d, J = 7.5 Hz, 2H), 7.43 (d, J = 7.5 Hz, 2H), 7.06 (s, 1H), 5.56 (s, 1H), 1.28 (s, 9H).





18
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.60 (dd, J = 2.0, 1.5 Hz, 1H), 7.53-7.45 (m, 1H), 7.39-7.30 (m, 2H), 7.06 (s, 1H), 5.60 (s, 1H), 1.33 (s, 9H).





19
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.47 (dd, J = 7.0, 2.5 Hz, 1H), 7.40-7.31 (m, 2H), 7.29 (dd, J = 6.5, 3.0 Hz, 1H), 7.03 (s, 1H), 5.64 (s, 1H), 1.24 (s, 9H).





20
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.58-7.52 (m, 2H), 7.45-7.38 (m, 2H), 7.01 (s, 1H), 6.40-6.33 (m, 1H), 6.15-6.01 (m, 1H), 5.78 (s, 1H), 1.72 (d, J = 6.5 Hz, 3H).





21
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.82-7.42 (m, 4H), 7.02 (s, 1H), 6.91-6.70 (m, 1H), 5.92 (s, 1H), 5.70-5.49 (m, 2H).





22
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.73 (d, J = 7.5 Hz, 2H), 7.67 (d, J = 7.5 Hz, 2H), 7.05 (s, 1H), 5.51 (s, 1H), 1.86 (s, 3H).





23
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.79 (dd, J = 2.0, 1.5 Hz, 1H), 7.57-7.35 (m, 3H), 7.06 (s, 1H), 5.53 (s, 1H), 3.14 (s, 1H).





24
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.47 (d, J = 7.5 Hz, 2H), 7.34 (d, J = 7.5 Hz, 2H), 7.06 (s, 1H), 5.53 (s, 1H), 1.93-1.84 (m, 1H), 1.20-1.11 (m, 2H), 0.92- 0.83 (m, 2H).





25
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.56 (d, J = 7.5 Hz, 2H), 7.44 (d, J = 7.5 Hz, 2H), 7.00 (s, 1H), 5.76 (s, 1H), 2.60-2.51 (m, 1H), 1.94-1.81 (m, 8H), 1.81- 1.71 (m, 2H).





26
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.60-7.51 (m, 1H), 7.39-7.16 m, 3H), 7.09 (s, 1H), 5.81 (s, 1H).





27
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.82-7.68 (m, 1H), 7.73 (dd, J = 2.0, 1.5 Hz, 1H), 7.42-7.37 (m, 2H), 7.07 (s, 1H), 5.51 (s, 1H).





28
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.70 (d, J = 7.5 Hz, 2H), 7.57 (d, J = 7.5 Hz, 2H), 7.00 (s, 1H), 5.78 (s, 1H).





29
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.99 (dd, J = 2.0, 1.5 Hz, 1H), 7.83-7.47 (m, 2H), 7.16-7.03 (m, 1H), 7.06 (s, 1H), 5.49 (s, 1H).





30
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.49-7.39 (m, 3H), 7.29-7.17 (m, 1H), 7.04 (s, 1H), 5.94 (s, 1H).





31
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.84 (dd, J = 2.0, 1.5 Hz, 1H), 7.64-7.31 (m, 1H), 7.01 (s, 1H), 5.80 (s, 1H).





32
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.44-7.16 (m, 2H), 7.11-6.95 (m, 2H), 7.07 (s, 2H), 5.48 (s, 1H).





33
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.89 (d, J = 7.5 Hz, 2H), 7.34 (d, J = 7.5 Hz, 2H), 7.06 (s, 1H), 5.47 (s, 1H).





34
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.45-7.38 (m, 2H), 7.30-7.14 (m, 1H), 7.01 (s, 1H), 5.68 (s, 1H).





35
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.41-7.35 (m, 2H), 7.02 (s, 1H), 6.95-6.76 (m, 1H), 5.82 (s, 1H).





36
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.71-7.57 (m, 1H), 7.22-7.06 (m, 2H), 7.11 (s, 1H), 5.20 (s, 1H).





37
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.52-7.44 (m, 3H), 7.04 (s, 1H), 5.94 (s, 1H).





38
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.69 (d, J = 2.0 Hz, 1H), 7.35 (dd, J = 7.5, 2.0 Hz, 1H), 7.26 (d, J = 7.5 Hz, 1H), 7.01 (s, 1H), 5.79 (s, 1H).





39
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.53 (d, J = 2.0 Hz, 1H), 7.48 (d, J = 7.5 Hz, 1H), 7.33 (dd, J = 7.5, 2.0 Hz, 1H), 7.04 (s, 1H), 5.93 (s, 1H).





40
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.71-7.45 (m, 3H), 7.01 (s, 1H), 5.81 (s, 1H).





41
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.48-7.41 (m, 3H), 7.03 (s, 1H), 5.58 (s, 1H).





42
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.70 (dd, J = 7.5, 2.0 Hz, 1H), 7.36 (dd, J = 8.0, 2.0 Hz, 1H), 7.28 (dd, J = 8.0, 7.5 Hz, 1H), 7.04 (s, 1H), 5.92 (s, 1H).





43
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.54-7.40 (m, 2H), 7.15-7.09 (m, 1H), 7.11 (s, 1H), 5.61 (s, 1H).





44
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.48-7.40 (m, 2H), 7.06-6.99 (m, 2H), 5.92 (s, 1H).





45
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.49-7.43 (m, 2H), 7.14-7.02 (m, 1H), 7.02 (s, 1H), 5.47 (s, 1H).





46
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.59-7.49 (m, 1H), 7.36-7.21 (m, 1H), 7.02 (s, 1H), 5.82 (s, 1H).





47
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.41-7.18 (m, 3H), 7.04 (s, 1H), 5.51 (s, 1H).





48
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.57-7.41 (m, 2H), 7.12 (s, 1H), 7.07-6.93 (m, 1H), 5.48 (s, 1H).





49
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.62-7.53 (m, 2H), 7.40-7.22 (m, 1H), 7.01 (s, 1H), 5.81 (s, 1H).





50
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.83-7.58 (m, 2H), 7.25-7.11 (m, 1H), 7.02 (s, 1H), 5.52 (s, 1H).





51
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.59-7.46 (m, 2H), 7.41-7.35 (m, 1H), 7.01 (s, 1H), 5.68 (s, 1H).





52
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.00 (s, 1H), 6.75-6.52 (m, 2H), 5.64 (s, 1H).





53
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.28-7.20 (m, 2H), 7.02 (s, 1H), 5.84 (s, 1H).





54
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.17-7.03 (m, 3H), 6.98-6.77 (m, 1H), 4.92 (s, 1H).





55
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.03 (s, 1H), 5.57 (s, 1H).





56
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.34 (dd, J = 9.0, 1.5 Hz, 1H), 7.24-7.07 (m, 1H), 7.17 (dd, J = 7.5, 2.5 Hz, 1H), 7.07 (s, 1H), 5.45 (s, 1H), 2.31 (s, 3H).





57
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.48-7.42 (m, 1H), 7.25-7.10 (m, 2H), 7.02 (s, 1H), 5.46 (s, 1H), 2.50 (s, 3H).





58
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.22-7.08 (m, 3H), 7.01 (s, 1H), 5.66 (s, 1H), 2.44 (s, 3H).





59
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.55-7.40 (m, 1H), 7.09 (s, 1H), 7.03-6.95 (m, 2H), 5.79 (s, 1H), 2.35 (s, 3H).





60
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.74-8.55 (m, 1H), 7.44-7.17 (m, 2H), 7.09 (s, 1H), 5.89 (s, 1H), 3.90 (s, 3H).





61
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.54 (dd, J = 5.5, 2.0 Hz, 1H), 8.27-8.03 (m, 1H), 7.44 (dd, J = 10.5, 7.5 Hz, 1H), 7.13 (s, 1H), 5.37 (s, 1H).





62
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.46-7.22 (m, 1H), 7.09-6.96 (m, 2H), 6.92- 6.76 (m, 1H), 5.58 (s, 1H), 3.90 (s, 3H).





63
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.74-7.64 (m, 2H), 7.39-7.22 (m, 2H), 6.51 (s, 1H).





64
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.71-7.64 (m, 2H), 7.61-7.46 (m, 1H), 7.11 (s, 1H), 5.86 (s, 1H), 5.60 (s, 1H).





65
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.93-7.78 (m, 1H), 7.60-7.39 (m, 2H), 7.07 (s, 1H), 5.84 (s, 1H), 5.41 (s, 1H).





66
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.27 (dd, J = 5.5, 2.0 Hz, 1H), 7.76-7.61 (m, 1H), 7.42 (dd, J = 10.5, 7.5 Hz, 1H), 7.06 (s, 1H), 5.47 (s, 1H).





67
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.73-7.56 (m, 1H), 7.51 (dd, J = 11.0, 2.0 Hz, 1H), 7.31 (s, 1H), 7.25-7.10 (m, 1H), 6.57 (s, 1H).





68
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.30-7.22 (m, 1H), 7.11-7.00 (m, 3H), 5.74 (s, 1H), 3.90 (s, 3H).





69
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.42 (d, J = 2.0 Hz, 1H), 8.19 (dd, J = 7.5, 2.0 Hz, 1H), 7.76 (d, J = 7.5 Hz, 1H), 7.06 (s, 1H), 5.75 (s, 1H).





70
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.54 (d, J = 7.5 Hz, 1H), 7.15 (d, J = 2.0 Hz, 1H), 7.00 (s, 1H), 6.90 (dd, J = 7.5, 2.0 Hz, 1H), 5.62 (s, 1H), 3.87 (s, 3H).





71
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.39-7.32 (m, 2H), 7.21 (dd, J = 7.5, 2.0 Hz, 1H), 7.04 (s, 1H), 5.66 (s, 1H), 2.34 (s, 3H).





72
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.48-7.42 (m, 2H), 7.25 (dd, J = 7.5, 2.0 Hz, 1H), 7.07 (s, 1H), 5.47 (s, 1H), 2.32 (s, 3H).





73
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.60 (d, J = 7.5 Hz, 1H), 7.07 (d, J = 2.0 Hz, 1H), 7.00 (s, 1H), 6.84 (dd, J = 7.5, 2.0 Hz, 1H), 5.63 (s, 1H), 3.81 (s, 3H).





74
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.60 (dd, J = 2.0, 1.5 Hz, 1H), 7.38-7.28 (m, 2H), 7.07 (s, 1H), 5.47 (s, 1H), 2.34 (s, 3H).





75
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.50 (d, J = 2.0 Hz, 1H), 7.29 (dd, J = 7.5, 2.0 Hz, 1H), 7.23 (d, J = 7.5 Hz, 1H), 7.07 (s, 1H), 5.48 (s, 1H), 2.28 (s, 3H).





76
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.38 (d, J = 7.5 Hz, 1H), 7.00 (s, 1H), 6.88-6.80 (m, 2H), 5.61 (s, 1H), 3.71 (s, 3H), 2.34 (s, 3H).





77
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.37 (d, J = 7.5 Hz, 1H), 7.10-7.02 (m, 2H), 7.04 (s, 1H), 5.68 (s, 1H), 2.36-2.29 (m, 6H).





78
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.33-7.16 (m, 3H), 7.03 (s, 1H), 5.60 (s, 1H), 2.30 (s, 6H).





79
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.52-7.38 (m, 3H), 7.01 (s, 1H), 5.78 (s, 1H), 1.33 (s, 6H).





80
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.97 (s, 1H), 7.09 (s, 1H), 7.03-6.95 (m, 2H), 3.82 (s, 3H), 3.76 (s, 3H), 3.72 (s, 3H).





81
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.02-6.91 (m, 3H), 5.63 (s, 1H), 4.34 (q, J = 8.0 Hz, 2H), 1.61 (t, J = 8.0 Hz, 3H).





82
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.25 (d, J = 7.5 Hz, 1H), 7.20-7.13 (m, 1H), 7.00 (s, 1H), 5.60 (s, 1H), 2.30 (s, 3H).





83
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.57 (d, J = 7.5 Hz, 2H), 7.09 (d, J = 7.5 Hz, 2H), 7.00 (s, 1H), 5.76 (s, 1H), 3.99 (t, J = 7.5 Hz, 2H), 1.75-1.61 (m, 2H), 1.14 (t, J = 8.0 Hz, 3H).





84
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.57-7.50 (m, 2H), 7.09-7.03 (m, 2H), 7.00 (s, 1H), 5.76 (s, 1H).





85
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.47-7.41 (m, 2H), 7.41-7.35 (m, 2H), 7.06 (s, 1H).





86
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.19 (dd, J = 8.0, 7.5 Hz, 1H), 7.13-7.02 (m, 3H), 6.93-6.78 (m, 1H).





87
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.38 (d, J = 7.5 Hz, 2H), 7.06 (s, 1H), 6.84 (d, J = 7.5 Hz, 2H), 5.57 (s, 1H), 4.92 (s, 1H).





88
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.15-7.01 (m, 2H), 7.03-6.97 (m, 1H), 6.72- 6.57 (m, 2H), 5.77 (s, 1H), 4.14 (s, 2H).





89
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.28 (d, J = 7.5 Hz, 2H), 7.87 (d, J = 7.5 Hz, 2H), 7.02 (s, 1H), 5.84 (s, 1H).





90
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.28-8.22 (m, 2H), 7.87-7.80 (m, 2H), 7.02 (s, 1H), 5.84 (s, 1H).





91
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.02 (d, J = 7.5 Hz, 2H), 7.77 (d, J = 7.5 Hz, 2H), 7.02 (s, 1H), 5.82 (s, 1H).





92
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.99-7.91 (m, 2H), 7.75-7.60 (m, 2H), 7.07 (s, 1H), 5.52 (s, 1H).





93
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.48 (d, J = 7.5 Hz, 2H), 7.06 (s, 1H), 6.80 (d, J = 7.5 Hz, 2H), 5.56 (s, 1H), 3.80 (s, 3H).





94
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.66-7.40 (m, 4H), 7.08 (s, 1H), 5.87 (s, 1H), 3.90 (s, 3H).





95
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.68 (dd, J = 2.0, 1.5 Hz, 1H), 7.46-7.35 (m, 3H), 7.01 (s, 1H), 5.80 (s, 1H), 2.50 (s, 3H).





96
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.61 (d, J = 7.5 Hz, 2H), 7.44 (d, J = 7.5 Hz, 2H), 7.01 (s, 1H), 5.77 (s, 1H), 3.25 (hept, J = 7.0 Hz, 1H), 1.40 (d, J = 7.0 Hz, 6H).





97
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.59 (d, J = 7.5 Hz, 2H), 7.05 (s, 1H), 6.70 (d, J = 7.5 Hz, 2H), 5.56 (s, 1H), 3.02 (s, 6H).





98
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.49 (d, J = 7.5 Hz, 2H), 7.16 (d, J = 7.5 Hz, 2H), 7.07 (s, 1H), 5.53 (s, 1H), 4.47-4.37 (m, 2H), 2.76-2.69 (m, 2H).





99
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.33-7.25 (m, 2H), 7.20-6.96 (m, 2H), 5.61 (s, 1H), 4.46 (q, J = 9.5 Hz, 2H).





100
CF3


embedded image








101
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.35-7.23 (m, 3H), 7.02-6.94 (m, 2H), 5.76 (s, 1H), 4.41 (hept, J = 7.0 Hz, 1H), 1.29 (d, J = 7.0 Hz, 6H).





102
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.53 (d, J = 7.0 Hz, 2H), 7.41 (d, J = 7.0 Hz, 2H), 7.06 (s, 1H), 5.54 (s, 1H), 2.83 (q, J = 8.0 Hz, 2H), 1.38 (t, J = 8.0 Hz, 3H).





103
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.19 (dd, J = 7.5, 7.0 Hz, 1H), 7.06 (s, 1H), 6.92- 6.70 (m, 2H), 6.63 (dd, J = 2.0, 1.5 Hz, 1H), 5.62 (s, 1H), 4.09 (s, 1H), 3.36 (q, J = 8.0 Hz, 2H), 1.23 (t, J = 8.0 Hz, 3H).





104
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.49 (d, J = 7.0 Hz, 2H), 7.19-7.03 (m, 3H), 5.47 (s, 1H), 5.14-4.91 (m, 1H), 4.04-3.91 (m, 2H).





105
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.85 (s, 1H), 7.58 (dd, J = 7.5, 2.0 Hz, 1H), 7.40-7.18 (m, 2H), 7.11 (dd, J = 7.0, 2.0 Hz, 1H), 7.08 (s, 1H), 4.38 (q, J = 8.0 Hz, 2H), 1.45 (t, J = 8.0 Hz, 3H).





106
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.96 (d, J = 8.0 Hz, 2H), 7.73 (s, 1H), 7.69 (d, J = 8.0 Hz, 2H), 7.01 (s, 1H), 5.78 (s, 1H), 2.10 (s, 3H).





107
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.08 (d, J = 7.0 Hz, 2H), 7.61 (d, J = 7.0 Hz, 2H), 7.07 (s, 1H), 5.49 (s, 1H), 3.95 (s, 3H).





108
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.51 (d, J = 7.5 Hz, 2H), 7.06 (d, J = 7.5 Hz, 2H), 7.00 (s, 1H), 5.61 (s, 1H), 2.29 (s, 3H).





109
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.71 (dd, J = 2.0, 1.5 Hz, 1H), 7.62-7.55 (m, 2H), 7.43 (dd, J = 8.0, 7.5 Hz, 1H), 7.01 (s, 1H), 5.77 (s, 1H), 4.47 (s, 2H), 3.58 (q, J = 8.0 Hz, 2H), 1.18 (t, J = 8.0 Hz, 3H).





110
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.84 (dd, J = 2.5, 1.5 Hz, 1H), 7.47-7.38 (m, 3H), 7.01 (s, 1H), 5.84 (s, 1H), 5.69 (s, 2H), 3.52 (s, 2H).





111
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.49 (d, J = 7.5 Hz, 2H), 7.39 (d, J = 7.5 Hz, 2H), 7.06 (s, 1H), 5.54 (s, 1H), 3.48-3.33 (m, 1H), 2.43-2.29 (m, 1H), 1.51- 1.33 (m, 1H).





112
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.58 (d, J = 7.5 Hz, 2H), 7.51 (d, J = 7.5 Hz, 2H), 7.06 (s, 1H), 5.53 (s, 1H), 3.71 (s, 2H), 2.47 (q, J = 8.0 Hz, 2H), 1.16 (t, J = 8.0 Hz, 3H).





113
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.99 (d, J = 7.5 Hz, 2H), 7.61 (d, J = 7.5 Hz, 2H), 7.07 (s, 1H), 5.58 (s, 1H), 2.51 (s, 3H).





114
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.98 (d, J = 7.5 Hz, 2H), 7.85 (d, J = 7.5 Hz, 2H), 7.07 (s, 1H), 5.53 (s, 1H), 3.30 (s, 3H).





115
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.19 (dd, J = 2.0, 1.5 Hz, 1H), 8.04-7.80 (m, 2H), 7.66 (dd, J = 8.0, 7.5 Hz, 1H), 7.07 (s, 1H), 5.43 (s, 1H), 3.25 (s, 3H).





116
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.95 (d, J = 7.5 Hz, 2H), 7.71 (d, J = 7.5 Hz, 2H), 7.07 (s, 1H), 5.53 (s, 1H), 4.07 (q, J = 6.5 Hz, 4H), 1.17 (t, J = 6.5 Hz, 6H).





117
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.86-7.79 (m, 4H), 7.62-7.56 (m, 2H), 7.37- 7.29 (m, 3H), 7.07 (s, 1H), 5.62 (s, 1H).





118
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.09-7.96 (m, 3H), 7.62-7.56 (m, 4H), 7.44- 7.28 (m, 4H), 7.37-7.29 (m, 2H), 7.02 (s, 1H), 5.84 (s, 1H).





119
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.49-7.38 (m, 3H), 7.28 (dd, J = 2.0, 1.5 Hz, 1H), 7.02 (s, 1H), 6.56 (s, 1H), 5.87 (s, 1H), 3.67 (s, 3H).





120
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.29 (s, 2H), 7.00 (s, 1H), 6.00-5.88 (m, 1H), 5.77 (s, 1H), 5.30-5.21 (m, 1H), 5.15- 5.04 (m, 1H), 4.05-3.99 (m, 2H), 3.29 (q, J = 8.0 Hz, 2H), 2.27 (s, 6H), 1.09 (t, J = 8.0 Hz, 3H).





121
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.23 (dd, J = 7.5, 7.0 Hz, 1H), 7.17-7.11 (m, 1H), 7.07 (s, 1H), 6.92-6.81 (m, 1H), 6.69 (dd, J = 2.0, 1.5 Hz, 1H), 5.54 (s, 1H), 5.18 (s, 2H), 4.22 (s, 1H), 2.97 (s, 3H).





122
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.56-7.37 (m, 3H), 7.20 (dd, J = 2.0, 1.5 Hz, 1H), 7.02 (s, 1H), 5.84 (s, 1H), 5.46 (s, 2H), 3.68 (s, 2H), 3.20 (s, 3H).





123
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.42-7.14 (m, 4H), 7.06 (s, 1H), 6.56 (s, 1H), 5.97 (s, 1H), 4.15 (q, J = 8.0 Hz, 2H), 1.26 (t, J = 8.1 Hz, 3H).





124
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.17 (dd, J = 7.5, 7.0 Hz, 1H), 7.05 (s, 1H), 6.94- 6.88 (m, 2H), 6.63 (dd, J = 2.0, 1.5 Hz, 1H), 5.61 (s, 1H), 4.09 (s, 2H), 3.00 (s, 3H), 2.76 (s, 1H).





125
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.36-7.29 (m, 1H), 7.25-7.17 (m, 5H), 7.10- 7.03 (m, 1H), 7.00 (s, 1H), 6.87-6.80 (m, 2H), 5.74 (s, 1H), 3.35 (s, 3H).





126
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.40-7.23 (m, 3H), 7.05 (s, 1H), 6.52 (dd, J = 2.0, 1.5 Hz, 1H), 6.39 (s, 1H), 6.01 (s, 1H), 2.99 (s, 3H).





127
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.20-7.21 (m, 3H), 7.08 (s, 1H), 6.55 (dd, J = 2.0, 1.5 Hz, 1H), 6.38 (s, 1H), 6.05 (s, 1H), 3.45 (q, J = 8.0 Hz, 2H), 1.59 (t, J = 8.0 Hz, 3H).





128
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.59 (d, J = 7.5 Hz, 2H), 7.27 (d, J = 7.5 Hz, 2H), 7.00 (s, 1H), 5.78 (s, 1H).





129
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.38 (dd, J = 7.5, 7.0 Hz, 1H), 7.13 (dd, J = 7.5, 2.0 Hz, 1H), 7.09 (s, 1H), 7.07 (dd, J = 7.0, 2.0 Hz, 1H), 6.02 (s, 1H), 5.77 (s, 2H), 3.13 (s, 3H), 2.33 (s, 3H).





130
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.42-7.37 (m, 1H), 7.33-7.24 (m, 2H), 7.01 (s, 1H), 7.04-6.97 (m, 1H), 5.81 (s, 1H), 4.71 (s, 2H).





131
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.41 (dd, J = 2.0, 1.5 Hz, 1H), 7.11 (dd, J = 2.5, 2.0 Hz, 1H), 7.06 (d, J = 2.5, 1.5 Hz, 1H), 7.00 (s, 1H), 5.48 (s, 1H), 4.68 (s, 2H), 3.00 (s, 1H).





132
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.33-7.23 (m, 3H), 7.03-6.96 (m, 2H), 5.77 (s, 1H), 3.92 (d, J = 6.5 Hz, 2H), 1.84- 1.73 (m, 2H), 1.77-1.61 (m, 3H), 1.65- 1.51 (m, 2H), 1.25-1.14 (m, 2H).





133
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.07-6.99 (m, 4H), 6.47 (dd, J = 2.0, 1.5 Hz, 1H), 5.77 (s, 1H), 4.99 (s, 2H), 4.21 (q, J = 8.0 Hz, 2H), 3.85 (s, 3H), 1.22 (t, J = 8.0 Hz, 3H).





134
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.38-7.30 (m, 4H), 7.20-7.08 (m, 3H), 7.05- 6.96 (m, 3H), 5.54 (s, 1H).





135
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.44-7.27 (m, 8H), 7.07 (s, 1H), 5.54 (s, 1H), 5.12 (s, 2H), 2.24 (s, 3H).





136
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.66 (d, J = 2.0 Hz, 1H), 7.49-7.27 (m, 6H), 7.17 (d, J = 7.5 Hz, 1H), 7.01 (s, 1H), 5.81 (s, 1H), 5.11 (s, 2H).





137
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.56 (d, J = 7.0 Hz, 2H), 7.50 (d, J = 7.0 Hz, 2H), 7.06 (s, 1H), 5.56 (s, 1H), 3.53 (s, 3H).





138
CF3


embedded image








139
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.03 (d, J = 7.5 Hz, 2H), 7.91 (d, J = 7.5 Hz, 2H), 7.01 (s, 1H), 5.79 (s, 1H), 3.51 (d, J = 7.0 Hz, 2H), 1.41-1.31 (m, 1H), 0.51- 0.39 (m, 2H), 0.36-0.26 (m, 2H).





140
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.33-7.23 (m, 3H), 7.08-7.00 (m, 2H), 5.60 (s, 1H), 4.88 (s, 2H), 4.02 (hept, J = 7.0 Hz, 1H), 3.72 (q, J = 8.0 Hz, 2H), 1.29 (d, J = 7.0 Hz, 6H), 1.23 (t, J = 8.0 Hz, 3H).





141
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.04 (s, 1H), 6.97-6.88 (m, 2H), 5.73 (s, 1H), 3.70 (s, 2H), 2.87 (hept, J = 6.5 Hz, 1H), 2.36 (s, 3H), 1.39 (d, J = 6.5 Hz, 6H).





142
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.52-7.44 (m, 2H), 7.48-7.40 (m, 2H), 7.07 (s, 1H), 6.57-6.48 (m, 2H), 6.40-6.34 (m, 2H), 5.63 (s, 1H), 4.43 (s, 1H), 4.32 (s, 2H), 2.19 (s, 3H).





143
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.12-8.04 (m, 3H), 7.02 (s, 1H), 5.83 (s, 1H).





144
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.04 (dd, J = 2.0, 1.5 Hz, 1H), 7.60-7.49 (m, 3H), 7.04 (s, 1H), 6.49-6.21 (m, 1H), 5.73 (s, 1H), 3.14-3.05 (m, 2H).





145
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.99 (d, J = 7.5 Hz, 2H), 7.91 (d, J = 7.5 Hz, 2H), 7.01 (s, 1H), 5.80 (s, 1H), 4.67 (s, 2H), 2.92 (hept, J = 6.5 Hz, 1H), 1.20-1.15 (m, 7H).





146
CF3


embedded image








147
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.20-8.08 (m, 1H), 7.89 (d, J = 7.5 Hz, 2H), 7.76 (d, J = 7.5 Hz, 2H), 7.49 (dd, J = 7.5, 7.0 Hz, 1H), 7.25-7.14 (m, 2H), 7.05 (s, 1H), 5.63 (s, 1H), 3.40 (s, 3H).





148
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.18 (dd, J = 2.0, 1.5 Hz, 1H), 7.82-7.77 (m, 2H), 7.65-7.54 (m, 2H), 7.01 (s, 1H), 6.87 (d, J = 1.5 Hz, 1H), 6.48 (d, J = 1.5 Hz, 1H), 5.82 (s, 1H), 3.25 (s, 3H).





149
CF3


embedded image








150
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.52 (d, J = 7.5 Hz, 2H), 7.46 (d, J = 7.5 Hz, 2H), 7.06 (s, 1H), 5.52 (s, 1H), 3.24-3.16 (m, 1H), 2.13-2.01 (m, 2H), 1.75- 1.63 (m, 4H), 1.55-1.38 (m, 2H).





151
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.06 (d, J = 7.5 Hz, 2H), 7.79 (d, J = 7.5 Hz, 2H), 7.07 (s, 1H), 5.46 (s, 1H), 4.40 (s, 2H).





152
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.06 (d, J = 7.5 Hz, 2H), 7.87 (d, J = 7.5 Hz, 2H), 7.01 (s, 1H), 5.80 (s, 1H), 4.45 (s, 1H), 2.53 (s, 3H).





153
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.90-7.78 (m, 2H), 7.67-7.56 (m, 4H), 7.37- 7.29 (m, 3H), 7.06 (s, 1H), 5.66 (s, 1H).





154
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.68-7.50 (m, 6H), 7.37-7.29 (m, 3H), 6.94 (s, 1H), 5.70 (s, 1H).





155
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.73 (d, J = 1.5 Hz, 1H), 8.63 (dd, J = 5.0, 1.0 Hz, 1H), 7.94-7.81 (m, 2H), 7.65-7.56 (m, 3H), 7.38-7.29 (m, 1H), 7.07 (s, 1H), 5.62 (s, 1H).





156
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.87-7.55 (m, 5H), 7.42-7.37 (m, 2H), 7.08 (s, 1H), 5.60 (s, 1H), 2.35 (s, 3H).





157
CF3


embedded image








158
CF3


embedded image








159
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.09 (d, J = 7.5 Hz, 2H), 7.87 (d, J = 7.5 Hz, 2H), 7.01 (s, 1H), 5.80 (s, 1H), 3.64-3.51 (m, 4H), 2.96-2.83 (m, 4H).





160
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.04 (s, 1H), 6.84 (s, 1H), 6.68 (s, 1H), 5.70 (s, 1H), 3.94 (s, 3H), 2.94 (s, 6H), 2.30 (s, 3H).





161
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.20 (s, 2H), 7.01 (s, 1H), 5.56 (s, 1H), 2.32 (s, 6H).





162
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.42 (d, J = 7.5 Hz, 1H), 7.36 (d, J = 7.5 Hz, 1H), 7.01 (s, 1H), 5.62 (s, 1H), 2.32 (s, 3H).





163
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.83 (d, J = 2.5 Hz, 1H), 7.66 (d, J = 2.5 Hz, 1H), 7.06 (s, 1H), 5.38 (s, 1H), 2.88 (q, J = 8.0 Hz, 2H), 1.27 (t, J = 8.0 Hz, 3H).





164
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.12 (d, J = 2.0 Hz, 1H), 7.63 (d, J = 2.0 Hz, 1H), 7.07 (s, 1H), 5.65 (s, 1H), 2.51 (s, 3H), 1.92-1.83 (m, 1H), 1.20-1.11 (m, 2H), 0.93-0.8l (m, 2H).





165
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.49 (s, 1H), 7.19 (t, J = 73.5 Hz, 1H), 7.07 (s, 1H), 7.01 (s, 1H), 5.64 (s, 1H).





166
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.68 (d, J = 10.5 Hz, 1H), 7.41 (d, J = 6.0 Hz, 1H), 7.13-7.09 (m, 2H), 5.58-5.29 (m, 3H).





167
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.45-7.33 (m, 2H), 7.13 (s, 1H), 6.75 (s, 1H), 5.07 (s, 1H), 3.24 (q, J = 8.0 Hz, 2H), 1.09 (t, J = 8.0 Hz, 3H).





168
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.62 (s, 2H), 7.54-7.48 (m, 2H), 7.44-7.36 (m, 3H), 7.08 (s, 1H), 5.54 (s, 1H).





169
CF3


embedded image



1H NMR (500 MHz, Chloroform-d) δ 7.48-7.38 (m, 1H), 7.22-7.16 (m, 2H), 7.08 (s, 1H), 6.79-6.74 (m, 2H), 5.42 (s, 1H).






170
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.28 (d, J = 2.0 Hz, 1H), 7.93 (s, 1H), 7.79 (dd, J = 7.5, 2.0 Hz, 1H), 7.20-7.10 (m, 2H), 3.45 (q, J = 6.8 Hz, 2H), 2.83 (s, 6H), 1.40 (t, J = 6.8 Hz, 3H).





171
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.39 (d, J = 7.5 Hz, 1H), 7.22-7.15 (m, 2H), 7.03 (s, 1H), 5.67 (s, 1H), 3.70 (s, 2H), 2.48 (q, J = 8.0 Hz, 2H), 2.30 (s, 3H), 1.24 (t, J = 8.0 Hz, 3H).





172
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.01 (d, J = 7.5 Hz, 1H), 7.58 (d, J = 7.5 Hz, 1H), 7.00 (s, 1H), 5.69 (s, 1H), 3.24-3.17 (m, 1H), 3.14 (s, 3H), 2.11-2.00 (m, 2H), 1.77-1.64 (m, 2H), 1.59-1.48 (m, 4H).





173
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.60 (dd, J = 7.5, 2.0 Hz, 1H), 7.54 (d, J = 7.5 Hz, 1H), 7.36 (d, J = 2.0 Hz, 1H), 6.99 (s, 1H), 5.68 (s, 1H), 3.07 (s, 1H), 2.67 (s, 1H).





174
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.50-7.40 (m, 2H), 7.26-7.11 (m, 1H), 7.03 (s, 1H), 5.66 (s, 1H), 5.34 (s, 1H), 2.61- 2.51 (m, 1H), 2.19-2.10 (m, 2H), 1.82- 1.71 (m, 4H), 1.54-1.34 (m, 4H).





175
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.25 (d, J = 2.0 Hz, 1H), 7.92 (d, J = 2.0 Hz, 1H), 7.02 (s, 1H), 5.64 (s, 1H), 3.12 (hept, J = 6.5 Hz, 1H), 1.30 (d, J = 6.5 Hz, 6H).





176
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.99 (d, J = 1.5 Hz, 1H), 7.66-7.43 (m, 2H), 7.01 (s, 1H), 5.80 (s, 1H), 4.19 (q, J = 8.0 Hz, 2H), 1.34 (t, J = 8.0 Hz, 3H).





177
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.35-7.29 (m, 2H), 7.06 (s, 1H), 6.96-6.89 (m, 1H), 6.57 (s, 1H), 5.62 (s, 1H).





178
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.21-7.10 (m, 1H), 7.06 (s, 1H), 6.81-6.62 (m, 2H), 5.39 (s, 1H), 4.39 (s, 1H), 3.87- 3.77 (m, 2H), 3.51-3.34 (m, 2H), 2.99- 2.89 (m, 1H), 1.92-1.71 (m, 2H), 1.27 (d, J = 6.5 Hz, 3H), 0.91 (t, J = 8.0 Hz, 3H).





179
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.78 (d, J = 11.0 Hz, 1H), 8.08 (d, J = 6.5 Hz, 1H), 7.12 (s, 1H), 5.49 (s, 1H), 2.66 (q, J = 8.0, Hz, 2H), 1.17 (t, J = 8.0 Hz, 3H).





180
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.10-7.01 (m, 3H), 6.64-6.56 (m, 3H), 5.83- 5.76 (m, 1H), 5.79 (s, 1H), 2.91-2.76 (m, 2H).





181
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.65 (s, 1H), 7.59 (d, J = 2.0 Hz, 1H), 7.53 (d, J = 7.5 Hz, 1H), 7.45 (dd, J = 7.5, 2.0 Hz, 1H), 7.29 (s, 1H), 6.15 (s, 1H).





182
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.25-8.17 (m, 3H), 7.33 (s, 1H), 7.10 (s, 1H), 5.54- 5.31 (m, 3H), 4.31 (q, J = 7.5 Hz, 2H), 1.34 (t, J = 7.5 Hz, 3H).





183
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.27 (s, 1H), 7.85 (dd, J = 7.5, 2.0 Hz, 1H), 7.62 (d, J = 7.5 Hz, 1H), 7.24 (d, J = 2.0 Hz, 1H), 7.02 (s, 1H), 5.72 (s, 1H), 2.10 (s, 3H).





184
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.33 (d, J = 2.0 Hz, 1H), 7.88 (dd, J = 7.5, 2.0 Hz, 1H), 7.80 (d, J = 7.5 Hz, 1H), 7.57 (d, J = 2.0 Hz, 2H), 7.45-7.37 (m, 1H), 7.08 (s, 1H), 6.46 (s, 2H), 5.62 (s, 1H).





185
CF3


embedded image








186
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.84-7.74 (m, 2H), 7.56 (d, J = 7.5 Hz, 1H), 7.04 (s, 1H), 5.63 (s, 1H), 3.39 (s, 6H), 2.34 (s, 3H).





187
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.67 (s, 1H), 7.87 (s, 1H), 7.63 (d, J = 7.5 Hz, 1H), 7.42 (dd, J = 7.5, 2.0 Hz, 1H), 7.16 (d, J = 2.0 Hz, 1H), 7.00 (s, 1H), 5.80 (s, 1H).





188
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.31 (s, 1H), 8.85 (d, J = 5.5 Hz, 1H), 8.75 (d, J = 5.5 Hz, 1H), 8.42-8.38 (m, 1H), 8.32 (dd, J = 7.5, 2.0 Hz, 1H), 7.72 (d, J = 7.5 Hz, 1H), 7.06 (s, 1H), 5.55 (s, 1H).





189
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.15-8.09 (m, 2H), 7.97-7.81 (m, 1H), 7.35- 7.21 (m, 2H), 7.03 (s, 1H), 6.34-6.20 (m, 2H), 5.84 (s, 1H).





190
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.63 (d, J = 7.5 Hz, 2H), 7.06 (s, 1H), 6.94 (d, J = 7.5 Hz, 2H), 5.58 (s, 1H), 3.49-3.43 (m, 4H), 1.67-1.57 (m, 6H).





191
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.23-7.06 (m, 2H), 6.95-6.72 (m, 3H), 5.51 (s, 1H), 3.74-3.55 (m, 4H), 3.33-3, 16 (m, 4H).





192
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.69 (d, J = 5.0 Hz, 2H), 7.96 (d, J = 5.0 Hz, 2H), 7.86-7.74 (m, 4H), 7.02 (s, 1H), 5.82 (s, 1H).





193
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.17 (s, 1H), 9.08 (s, 2H), 7.98-7.82 (m, 1H), 7.65-7.38 (m, 3H), 7.12 (s, 1H), 5.67 (s, 1H).





194
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.64-7.57 (m, 2H), 7.37 (d, J = 2.0 Hz, 1H), 7.06- 7.00 (m, 2H), 6.68-6.54 (m, 2H), 6.14 (s, 1H), 3.87 (s, 3H).





195
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.61 (d, J = 2.0 Hz, 1H), 7.50 (d, J = 2.0 Hz, 1H), 7.30 (d, J = 2.5 Hz, 1H), 7.05 (s, 1H), 6.71 (d, J = 2.5 Hz, 1H), 2.36 (s, 3H).





196
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.78 (s, 1H), 7.47-7.41 (m, 2H), 7.32-7.25 (m, 2H), 7.09 (s, 1H), 6.34-6.23 (m, 1H), 5.60 (s, 1H).





197
CF3


embedded image








198
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.97 (s, 1H), 7.96 (d, J = 7.5 Hz, 2H), 7.85 (s, 1H), 7.83 (d, J = 7.5 Hz, 2H), 7.02 (s, 1H), 5.82 (s, 1H).





199
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.53 (s, 1H), 8.43 (s, 1H), 7.64 (s, 2H), 7.04 (s, 1H), 5.64 (s, 1H).





200
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.32 (s, 1H), 7.89 (d, J = 2.0 Hz, 1H), 7.64 (dd, J = 7.5, 2.0 Hz, 1H), 7.31 (d, J = 7.5 Hz, 1H), 7.04 (s, 1H), 2.67 (s, 3H).





201
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.64-7.57 (m, 2H), 7.37 (d, J = 2.0 Hz, 1H), 7.06- 6.99 (m, 2H), 6.69-6.54 (m, 2H), 6.14 (s, 1H), 3.87 (s, 3H).





202
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.37 (s, 1H), 9.18 (d, J = 2.5 Hz, 1H), 8.68- 8.56 (m, 2H), 7.56-7.41 (m, 1H), 7.28 (s, 1H).






203
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.68 (d, J = 5.0 Hz, 1H), 7.56-7.50 (m, 2H), 7.24 (s, 1H), 5.80 (s, 1H), 2.69 (s, 3H).





204
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.66 (s, 1H), 8.79 (s, 1H), 8.55 (d, J = 5.0 Hz, 1H), 7.46 (dd, J = 5.0 Hz, 1H), 7.26 (s, 1H).






205
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.09 (s, 1H), 8.55-8.43 (m 1H), 8.02-7.89 (m, 1H), 7.59-7.40 (m, 1H), 7.36 (s, 1H).






206
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.45 (dd, J = 5.5, 5.0 Hz, 1H), 7.63-7.52 (m, 1H), 7.42 (dd, J = 8.0, 1.0 Hz, 1H), 7.30 (s, 1H), 5.34 (s, 1H).





207
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.65 (s, 1H), 8.80-8.57 (m, 2H), 7.36-7.34 (m, 2H).






208
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.20 (d, J = 1.5 Hz, 1H), 9.07 (d, J = 2.0 Hz, 1H), 8.40 (dd, J = 2.0, 1.5 Hz, 1H), 8.40 (s, 1H), 7.31 (s, 1H), 5.41 (s, 1H).





209
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.09 (d, J = 1.5 Hz, 1H), 8.02 (dd, J = 8.0, 1.5 Hz, 1H), 7.47 (d, J = 8.0 Hz, 1H), 7.30 (s, 1H), 5.34 (s, 1H), 3.26 (t, J = 8.0 Hz, 2H), 1.86-1.67 (m, 2H), 1.01 (t, J = 8.0 Hz, 3H).





210
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.61 (dd, J = 5.0, 1.5 Hz, 1H), 7.85 (dd, J = 8.0, 1.5 Hz, 1H), 7.49 (dd, J = 8.0, 5.0 Hz, 1H), 7.25 (s, 1H), 6.72 (dd, J = 16.5, 10.0 Hz, 1H), 6.19 (dd, J = 13.5, 10.0 Hz, 1H), 5.67 (dd, J = 16.5, 13.5 Hz, 1H), 5.60 (s, 1H).





211
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.41 (s, 1H), 8.97 (s, 1H), 8.52 (s, 1H), 8.20 (s, 1H), 7.29 (s, 1H), 2.38 (s, 3H).






212
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.18 (d, J = 1.5 Hz, 1H), 8.24 (dd, J = 8.0, 1.5 Hz, 1H), 8.02 (d, J = 8.0 Hz, 1H), 7.32 (s, 1H), 5.20 (s, 1H).





213
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.45 (s, 1H), 8.32 (dd, J = 5.0, 1.5 Hz, 1H), 7.79 (dd, J = 6.5, 1.5 Hz, 1H), 7.36 (s, 1H), 7.11 (dd, J = 6.5, 5.0 Hz, 1H), 4.32 (q, J = 7.0 Hz, 2H), 1.19 (t, J = 7.0 Hz, 3H).






214
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.91 (s, 1H), 8.53 (s, 1H), 7.80 (s, 1H), 7.24 (s, 1H), 5.81 (s, 1H), 1.71-1.60 (m, 1H), 1.07-0.98 (m, 2H), 0.79-0.70 (m, 2H).





215
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.19 (d, J = 1.5 Hz, 1H), 8.11 (dd, J = 7.0, 1.5 Hz, 1H), 7.52 (d, J = 7.0 Hz, 1H), 7.30 (s, 1H), 5.36 (s, 1H), 2.61-2.42 (m, 2H), 1.85-1.73 (m, 7H), 1.28-1.20 (m, 2H).





216
CF3


embedded image








217
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.80 (d, J = 1.5 Hz, 1H), 8.48 (d, J = 2.0 Hz, 1H), 7.87 (dd, J = 2.0, 1.5 Hz, 1H), 7.28 (s, 1H), 5.51 (s, 1H), 4.72-4.16 (m, 3H), 3.00-2.76 (m, 2H).





218
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.93 (s, 2H), 7.26 (s, 1H), 5.74 (s, 1H).





219
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.75 (dd, J = 4.5, 1.5 Hz, 1H), 7.76 (dd, J = 6.0, 1.5 Hz, 1H), 7.24 (s, 1H), 5.81 (s, 1H), 2.33 (s, 3H).





220
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.36 (s, 1H), 7.52 (s, 1H), 7.45-7.25 (m, 2H).






221
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.40 (s, 1H), 8.20 (d, J = 4.5 Hz, 1H), 7.34 (d, J = 10.5 Hz, 1H), 7.22 (s, 1H), 2.22 (s, 3H).






222
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.48 (d, J = 5.0 Hz, 1H), 7.74 (d, J = 5.0 Hz, 1H), 7.24 (s, 1H), 5.68 (s, 1H).





223
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.11 (dd, J = 8.0, 5.0 Hz, 1H), 7.24 (s, 1H), 6.84 (dd, J = 8.0, 7.5 Hz, 1H), 5.67 (s, 1H), 2.83 (s, 3H).





224
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.11 (s, 1H), 7.24 (s, 1H), 6.84 (s, 1H), 5.67 (s, 1H).





225
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.59 (s, 1H), 8.87 (s, 1H), 8.42 (s, 1H), 7.33 (s, 1H), 2.43 (s, 3H).






226
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.16 (s, 1H), 8.88 (d, J = 2.5 Hz, 1H), 8.35 (dd, J = 8.5, 2.5 Hz, 1H), 7.29 (s, 1H), 6.98 (d, J = 8.5 Hz, 1H), 3.93 (s, 3H).






227
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.61 (s, 1H), 8.33 (d, J = 5.0 Hz, 1H), 7.82 (d, J = 7.5 Hz, 1H), 7.33 (s, 1H), 7.16 (dd, J = 7.5, 5.0 Hz, 1H), 3.84 (s, 3H).






228
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.02 (s, 1H), 7.30 (s, 1H), 5.42 (s, 1H), 4.76- 4.38 (m, 2H), 3.19-3.02 (m, 1H), 2.08- 1.94 (m, 2H), 1.39 (d, J = 7.0 Hz, 3H).





229
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.96 (s, 1H), 7.53 (s, 1H), 7.23 (s, 1H), 6.89 (s, 1H), 5.80 (s, 1H), 4.47-4.37 (m, 2H), 3.08-2.91 (m, 2H).





230
CF3


embedded image








231
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.56 (s, 1H), 7.41 (s, 1H), 7.35 (s, 1H), 4.45 (s, 1H), 3.50 (s, 1H), 3.11-3.01 (m, 1H), 0.65-0.55 (m, 2H), 0.43-0.31 (m, 2H).





232
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.42 (s, 1H), 7.25 (s, 1H), 7.11 (s, 1H), 5.68 (s, 1H), 4.90 (hept, J = 7.0 Hz, 1H), 1.29 (d, J = 7.0 Hz, 6H).





233
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.00 (d, J = 1.5 Hz, 1H), 7.52 (d, J = 1.5 Hz, 1H), 7.29 (s, 1H), 5.17 (s, 1H), 5.03 (q, J = 7.0 Hz, 2H), 2.98 (hept, J = 7.5 Hz, 1H), 1.30 (d, J = 7.5 Hz, 6H).





234
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.92 (d, J = 8.0 Hz, 1H), 7.24 (s, 1H), 6.92 (d, J = 8.0 Hz, 1H), 5.68 (s, 1H), 4.68 (s, 2H), 2.99 (s, 1H).





235
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.66 (d, J = 1.0 Hz, 1H), 8.61 (d, J = 1.5 Hz, 1H), 7.90 (dd, J = 1.5, 1.0 Hz, 1H), 7.32 (s, 1H), 5.20 (s, 1H), 2.39-2.26 (m, 1H), 1.05-0.95 (m, 2H), 0.53-0.44 (m, 2H).





236
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.88 (d, J = 1.5 Hz, 1H), 7.94 (dd, J = 8.0, 1.5 Hz, 1H), 7.38 (d, J = 8.0 Hz, 1H), 7.23 (s, 1H), 5.78 (s, 1H), 2.97 (q, J = 8.0 Hz, 2H), 1.36 (t, J = 8.0 Hz, 3H).





237
CF3


embedded image








238
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.89 (d, J = 1.0 Hz, 1H), 7.94 (dd, J = 8.0, 1.0 Hz, 1H), 7.39 (d, J = 8.0 Hz, 1H), 7.23 (s, 1H), 5.79 (s, 1H), 3.78 (t, J = 7.5 Hz, 2H), 3.21 (t, J = 7.5 Hz, 2H).





239
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.14 (d, J = 1.0 Hz, 1H), 8.04-7.96 (m, 2H), 7.77- 7.71 (m, 2H), 7.31-7.22 (m, 3H), 5.59 (s, 1H), 2.33 (s, 3H).





240
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.66 (d, J = 1.0 Hz, 1H), 7.87 (dd, J = 8.0, 1.0 Hz, 1H), 7.47-7.39 (m, 2H), 7.31 (s, 1H), 7.18-7.12 (m, 2H), 7.09 (d, J = 8.0 Hz, 1H), 6.96-6.83 (m, 1H), 5.37 (s, 1H).





241
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.22 (d, J = 1.0 Hz, 1H), 8.11 (dd, J = 8.0, 1.0 Hz, 1H), 7.54 (d, J = 8.0 Hz, 1H), 7.32- 7.23 (m, 3H), 7.19-7.11 (m, 1H), 7.14- 7.06 (m, 2H), 5.32 (s, 1H), 4.21 (s, 2H).





242
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.69 (d, J = 1.0 Hz, 1H), 7.85 (dd, J = 8.0, 1.0 Hz, 1H), 7.48-7.40 (m, 3H), 7.33-7.27 (m, 2H), 6.97 (d, J = 8.0 Hz, 1H), 5.31 (s, 1H).





243
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.07 (s, 1H), 7.23 (s, 1H), 7.06 (s, 1H), 5.75 (s, 1H), 4.04 (s, 2H), 3.50 (s, 2H), 2.47 (q, J = 8.0 Hz, 2H), 1.22 (t, J = 8.0 Hz, 3H).





244
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.23 (d, J = 8.0 Hz, 1H), 7.71 (d, J = 8.0 Hz, 1H), 7.36 (s, 1H), 6.70 (s, 1H), 3.98 (s, 3H), 3.28 (s, 6H).





245
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.26 (s, 1H), 8.62 (s, 1H), 7.54 (s, 1H), 7.42 (s, 1H), 7.36-7.25 (m, 2H), 7.22-7.11 (m, 2H), 3.18 (s, 3H).





246
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.13 (d, J = 1.0 Hz, 1H), 8.44 (d, J = 8.0 Hz, 1H), 8.15 (dd, J = 8.0, 1.0 Hz, 1H), 7.83 (s, 1H), 7.30 (s, 1H), 5.42 (s, 1H), 2.16 (s, 3H).





247
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.92 (d, J = 1.0 Hz, 1H), 8.61 (d, J = 1.5 Hz, 1H), 7.98 (dd, J = 1.5, 1.0 Hz, 1H), 7.24 (s, 1H), 5.83 (s, 1H), 5.72 (s, 2H), 3.52 (s, 2H).





248
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.08 (d, J = 1.0 Hz, 1H), 8.05 (dd, J = 8.0, 1.0 Hz, 1H), 7.37-7.18 (m, 5H), 7.03-6.92 (m, 1H), 6.78 (d, J = 8.0 Hz, 1H), 5.83 (s, 1H), 3.70 (s, 3H).





249
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.29 (d, J = 1.0 Hz, 1H), 8.22 (dd, J = 8.0, 1.0 Hz, 1H), 7.56-7.46 (m, 3H), 7.33-7.20 (m, 1H), 7.24 (s, 2H), 5.79 (s, 1H), 4.21 (s, 2H).





250
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.71 (d, J = 1.0 Hz, 1H), 7.84 (dd, J = 8.0, 1.0 Hz, 1H), 7.48-7.40 (m, 4H), 7.31 (s, 1H), 6.98 (d, J = 8.0 Hz, 1H), 5.38 (s, 1H), 5.31 (s, 2H).





251
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.15 (d, J = 1.0 Hz, 1H), 8.10 (dd, J = 8.0, 1.0 Hz, 1H), 7.24 (s, 1H), 7.23-7.15 (m, 2H), 6.95-6.88 (m, 2H), 6.82-6.74 (m, 2H), 5.89 (s, 1H), 2.86 (s, 3H).





252
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.94 (d, J = 1.0 Hz, 1H), 7.90 (dd, J = 8.0, 1.0 Hz, 1H), 7.28 (s, 1H), 6.58 (d, J = 8.0 Hz, 1H), 5.51 (s, 1H), 4.48 (s, 2H), 3.26 (q, J = 8.0 Hz, 2H), 2.13 (s, 3H), 0.93 (t, J = 8.0 Hz, 3H).





253
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.61 (d, J = 1.0 Hz, 1H), 7.88 (dd, J = 8.0, 1.0 Hz, 1H), 7.23 (s, 1H), 6.92 (d, J = 8.0 Hz, 1H), 5.78 (s, 1H), 5.08 (d, J = 63.5 Hz, 2H).





254
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.23 (d, J = 1.0 Hz, 1H), 8.25 (dd, J = 8.0, 1.0 Hz, 1H), 8.19 (d, J = 8.0 Hz, 1H), 7.26 (s, 1H), 5.70 (s, 1H), 4.65 (s, 2H).





255
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.23 (d, J = 1.0 Hz, 1H), 8.18 (dd, J = 8.0, 1.0 Hz, 1H), 7.31 (d, J = 8.0 Hz, 1H), 7.23 (s, 1H), 5.78 (s, 1H), 4.04 (s, 2H), 3.58 (t, J = 8.0 Hz, 2H), 2.95 (t, J = 8.0 Hz, 2H).





256
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.96 (d, J = 1.5 Hz, 1H), 7.97 (dd, J = 8.0, 1.5 Hz, 1H), 7.24 (s, 1H), 6.58 (d, J = 8.0 Hz, 1H), 5.80 (s, 1H), 5.44 (s, 2H), 3.45 (q, J = 8.0 Hz, 2H), 3.24 (s, 3H), 1.33 (t, J = 8.0 Hz, 3H).





257
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.91 (d, J = 1.0 Hz, 1H), 7.89 (dd, J = 7.5, 1.0 Hz, 1H), 7.23 (s, 1H), 6.78 (d, J = 7.5 Hz, 1H), 5.66 (s, 1H), 2.86 (s, 3H), 2.27 (q, J = 8.0 Hz, 2H), 1.07 (t, J = 8.0 Hz, 3H).





258
CF3


embedded image








259
CF3


embedded image








260
CF3


embedded image








261
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.86 (d, J = 1.0 Hz, 1H), 8.63 (d, J = 1.5 Hz, 1H), 8.00 (dd, J = 1.5, 1.0 Hz, 1H), 7.31 (s, 1H), 5.22 (s, 1H), 4.54 (s, 2H), 4.31- 3.54 (m, 4H).





262
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.41 (d, J = 1.0 Hz, 1H), 8.09 (d, J = 1.5 Hz, 1H), 7.29-7.21 (m, 2H), 6.00-5.78 (m, 1H), 5.29-5.10 (m, 2H), 4.26 (s, 1H), 3.99-3.77 (m, 2H).





263
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.41 (dd, J = 5.5, 1.0 Hz, 1H), 8.09-8.00 (m, 2H), 7.29-7.21 (m, 2H), 5.78 (s, 1H).





264
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.26 (dd, J = 8.0, 1.0 Hz, 1H), 8.04 (dd, J = 7.5, 1.0 Hz, 1H), 7.92 (dd, J = 8.0, 7.5 Hz, 1H), 7.14 (s, 1H), 5.76 (s, 1H).





265
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.75 (dd, J = 5.0, 1.0 Hz, 1H), 7.85 (dd, J = 8.0, 1.0 Hz, 1H), 7.49 (dd, J = 8.0, 5.0 Hz, 1H), 7.14 (s, 1H), 5.46 (s, 1H).





266
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.67 (d, J = 5.0 Hz, 1H), 7.45 (dd, J = 5.0, 1.0 Hz, 1H), 7.28 (d, J = 1.0 Hz, 1H), 7.12 (s, 1H), 5.66 (s, 1H), 2.38 (s, 3H).





267
CF3


embedded image








268
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.60 (dd, J = 5.0, 1.0 Hz, 1H), 7.54 (dd, J = 8.0, 1.0 Hz, 1H), 7.37 (dd, J = 8.0, 5.0 Hz, 1H), 7.14 (s, 1H), 5.36 (s, 1H), 3.38-3.29 (m, 1H), 2.04-1.92 (m, 4H), 1.74- 1.57 (m, 4H).





269
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.52 (d, J = 1.0 Hz, 1H), 7.82 (d, J = 8.0 Hz, 1H), 7.56 (dd, J = 8.0, 1.0 Hz, 1H), 7.08 (s, 1H), 5.73 (s, 1H), 2.47 (d, J = 7.5 Hz, 2H), 1.94-1.82 (m, 1H), 0.92 (d, J = 7.0 Hz, 6H).





270
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.61 (dd, J = 8.0, 7.5 Hz, 1H), 7.23 (dd, J = 8.0, 1.0 Hz, 1H), 7.13 (s, 1H), 6.87 (dd, J = 8.0, 1.0 Hz, 1H), 5.75 (s, 1H), 5.03 (q, J = 9.0 Hz, 2H).





271
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.65 (dd, J = 8.0, 7.5 Hz, 1H), 7.26 (dd, J = 8.0, 1.0 Hz, 1H), 7.17 (s, 1H), 6.89 (dd, J = 8.0, 1.0 Hz, 1H), 5.98 (s, 1H), 5.86-5.66 (m, 1H), 4.32-4.26 (m, 2H).





272
CF3


embedded image








273
CF3


embedded image








274
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.11 (s, 1H), 6.58 (s, 1H), 6.15 (s, 1H), 4.71 (s, 1H), 2.84 (s, 3H), 2.28 (s, 3H).





275
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.11 (s, 1H), 6.58 (dd, J = 10.5, 7.5 Hz, 1H), 6.15 (dd, J = 7.5, 5.5 Hz, 1H), 5.71 (s, 1H), 2.28 (s, 3H).





276
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.23 (d, J = 1.0 Hz, 1H), 8.05 (d, J = 1.0 Hz, 1H), 7.10 (s, 1H), 5.82 (s, 1H), 4.04 (s, 2H), 3.12 (s, 3H), 2.47 (q, J = 8.0 Hz, 2H), 1.24 (t, J = 8.0 Hz, 3H).





277
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.72 (d, J = 1.0 Hz, 1H), 8.01 (d, J = 8.0 Hz, 1H), 7.81 (dd, J = 8.0, 1.0 Hz, 1H), 7.12 (s, 1H), 5.62 (s, 1H), 4.54 (s, 2H), 4.31- 4.21 (m, 2H), 3.60-3.54 (m, 2H).





278
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.54 (d, J = 5.1 Hz, 2H), 7.68 (d, J = 5.1 Hz, 2H), 7.31 (s, 1H), 5.31 (s, 1H).





279
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.58-8.49 (m, 2H), 7.61 (d, J = 5.0 Hz, 1H), 7.27 (s, 1H), 5.82 (s, 1H).





280
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.65 (d, J = 5.0 Hz, 1H), 7.58 (d, J = 1.0 Hz, 1H), 7.46 (dd, J = 5.0, 1.0 Hz, 1H), 7.30 (s, 1H), 5.35 (s, 1H), 1.33 (s, 9H).





281
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.12 (d, J = 5.0 Hz, 1H), 7.24 (s, 1H), 7.13 (d, J = 1.0 Hz, 1H), 7.01 (dd, J = 5.0, 1.0 Hz, 1H), 5.81 (s, 1H), 4.90 (hept, J = 7.0 Hz, 1H), 1.29 (d, J = 7.0 Hz, 6H).





282
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.67 (d, J = 8.0 Hz, 1H), 7.41 (d, J = 5.0 Hz, 1H), 7.26 (s, 1H), 6.31 (s, 1H), 4.12-4.02 (m, 2H), 3.43-3.31 (m, 1H), 1.79- 1.73 (m, 2H), 1.33 (d, J = 7.0 Hz, 3H).





283
CF3


embedded image








284
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.05 (d, J = 1.0 Hz, 1H), 7.67 (d, J = 1.0 Hz, 1H), 7.26 (s, 1H), 5.96-5.86 (m, 1H), 5.84 (s, 1H), 4.30-4.20 (m, 2H).





285
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.73 (d, J = 5.0 Hz, 1H), 7.76 (d, J = 5.0 Hz, 1H), 7.24 (s, 1H), 5.62 (s, 1H), 2.66 (q, J = 8.0 Hz, 2H), 2.45 (s, 3H), 1.22 (t, J = 8.0 Hz, 3H).





286
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.61 (s, 1H), 8.34 (s, 1H), 7.36 (s, 1H), 6.36 (s, 1H), 4.52 (s, 2H), 3.58 (q, J = 8.0 Hz, 2H), 3.26 (q, J = 8.0 Hz, 2H), 2.95 (s, 3H), 1.15 (d, J = 8.0 Hz, 3H), 1.10 (d, J = 8.0 Hz, 3H).





287
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.37 (s, 1H), 7.46-7.40 (m, 2H), 7.44-7.34 (m, 2H), 7.37-7.27 (m, 1H), 7.31 (s, 1H), 7.18 (s, 1H), 5.66 (s, 1H), 5.28 (s, 2H), 2.32 (s, 3H).





288
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.15 (s, 1H), 8.89 (d, J = 2.0 Hz, 1H), 8.25 (dd, J = 7.0, 2.0 Hz, 1H), 7.19 (s, 1H), 6.94 (d, J = 7.0 Hz, 1H), 3.69-3.57 (m, 4H), 3.55-3.38 (m, 4H).






289
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.31 (s, 1H), 7.26 (s, 1H), 6.96 (s, 1H), 6.80- 6.61 (m, 1H), 5.85 (s, 1H), 5.72-5.43 (m, 2H), 2.32 (s, 3H).





290
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.29 (s, 1H), 7.25 (s, 1H), 5.75 (s, 1H), 4.07 (q, J = 8.0 Hz, 4H), 2.48 (s, 3H), 1.20 (t, J = 8.0 Hz, 6H).





291
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.38 (d, J = 5.0 Hz, 1H), 8.31 (s, 1H), 7.62 (d, J = 5.0 Hz, 1H), 7.29 (t, J = 73.5 Hz, 1H), 7.25 (s, 2H), 7.02 (s, 1H), 5.70 (s, 1H).





292
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.87 (d, J = 1.0 Hz, 1H), 8.55 (d, J = 1.5 Hz, 1H), 7.98 (dd, J = 1.5, 1.0 Hz, 1H), 7.28 (s, 1H), 5.72 (s, 1H), 4.52 (s, 2H), 3.36 (s, 3H).





293
CF3


embedded image








294
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.83 (d, J = 5.0 Hz, 1H), 8.42 (d, J = 1.0 Hz, 1H), 7.98 (dd, J = 5.0, 1.0 Hz, 1H), 7.24 (s, 1H), 5.79 (s, 1H), 3.55 (s, 2H), 2.20 (s, 3H).





295
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.11 (d, J = 1.0 Hz, 1H), 8.05 (dd, J = 8.0, 1.0 Hz, 1H), 7.32-7.23 (m, 2H), 5.38 (s, 1H), 4.03 (s, 2H), 2.48 (q, J = 8.0 Hz, 2H), 1.27 (t, J = 8.0 Hz, 3H).





296
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.73 (d, J = 1.0 Hz, 1H), 7.53 (d, J = 1.0 Hz, 1H), 7.11 (s, 1H), 3.77 (s, 2H), 2.91 (s, 3H).





297
CF3


embedded image








298
CF3


embedded image








299
CF3


embedded image








300
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.06 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 7.94 (dd, J = 2.0, 1.5 Hz, 1H), 7.75 (d, J = 5.0 Hz, 1H), 7.55 (dd, J = 2.5, 1.5 Hz, 1H), 7.44 (dd, J = 2.5, 2.0 Hz, 1H), 7.28 (s, 1H), 5.63 (s, 1H), 3.81 (s, 3H), 3.12 (s, 3H).





301
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.11 (d, J = 1.0 Hz, 1H), 8.96 (d, J = 1.5 Hz, 1H), 8.36 (dd, J = 1.5, 1.0 Hz, 1H), 7.68- 7.63 (m, 1H), 7.25 (s, 1H), 7.09-6.92 (m, 2H), 5.89 (s, 1H), 4.33 (s, 1H), 3.95 (s, 3H), 2.83 (s, 3H).





302
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.90 (d, J = 1.0 Hz, 1H), 7.76 (d, J = 2.5 Hz, 1H), 7.48 (d, J = 1.0 Hz, 1H), 7.13 (s, 1H), 6.75 (d, J = 2.5 Hz, 1H), 2.69 (s, 3H).





303
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.76 (d, J = 5.0 Hz, 1H), 7.77 (d, J = 1.0 Hz, 1H), 7.64 (dd, J = 5.0, 1.0 Hz, 1H), 7.27 (d, J = 2.5 Hz, 1H), 7.24 (s, 1H), 7.00 (dd, J = 2.5, 2.0 Hz, 1H), 6.88 (d, J = 2.0 Hz, 1H), 5.80 (s, 1H), 4.41 (s, 2H).





304
CF3


embedded image








305
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.66 (d, J = 1.5 Hz, 1H), 7.83 (d, J = 8.0 Hz, 1H), 7.66 (dd, J = 8.0, 1.5 Hz, 1H), 7.10 (s, 1H), 5.44 (s, 1H), 4.67 (s, 2H), 2.59 (q, J = 8.0 Hz, 4H), 1.17 (t, J = 8.0 Hz, 6H).





306
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.66 (s, 1H), 8.51 (d, J = 5.0 Hz, 1H), 7.48 (d, J = 5.0 Hz, 1H), 7.42 (s, 1H), 6.07 (s, 1H), 3.28 (s, 2H), 2.34 (s, 6H).





307
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.72 (d, J = 1.5 Hz, 1H), 8.66 (d, J = 1.0 Hz, 1H), 8.12 (dd, J = 1.5, 1.0 Hz, 1H), 7.29 (s, 1H), 5.54 (s, 1H), 3.84 (s, 3H), 3.70 (s, 2H).





308
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.63 (d, J = 5.0 Hz, 1H), 7.79 (d, J = 1.0 Hz, 1H), 7.38 (dd, J = 5.0, 1.0 Hz, 1H), 7.12 (s, 1H), 3.69 (s, 3H), 3.59 (s, 2H).





309
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.67 (d, J = 5.0 Hz, 1H), 7.88 (d, J = 1.0 Hz, 1H), 7.64 (dd, J = 5.0, 1.0 Hz, 1H), 7.30 (s, 1H), 5.67 (s, 2H), 5.33 (s, 1H), 2.69 (hept, J = 6.5 Hz, 1H), 1.24 (d, J = 6.5 Hz, 6H).





310
CF3


embedded image








311
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.60 (d, J = 5.0 Hz, 1H), 7.99 (d, J = 1.0 Hz, 1H), 7.28 (dd, J = 5.0, 1.0 Hz, 1H), 7.14 (s, 1H), 6.87 (dd, J = 2.0, 1.0 Hz, 1H), 6.72- 6.56 (m, 3H), 4.48 (s, 1H), 3.95 (q, J = 8.0 Hz, 2H), 2.78 (s, 3H), 1.91-1.81 (m, 1H), 1.20 (t, J = 8.0 Hz, 3H), 1.14- 1.05 (m, 2H), 0.78-0.69 (m, 2H).





312
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.41 (d, J = 5.0 Hz, 1H), 8.23 (s, 1H), 7.59 (d, J = 5.0 Hz, 1H), 7.29 (s, 1H), 6.11 (s, 1H), 4.31 (s, 2H), 3.39 (s, 3H).





313
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.60 (d, J = 1.5 Hz, 1H), 8.12 (d, J = 1.0 Hz, 1H), 7.53 (dd, J = 1.5, 1.0 Hz, 1H), 7.24 (s, 1H), 5.81 (s, 1H), 4.22 (t, J = 6.5 Hz, 2H), 2.87 (t, J = 6.5 Hz, 2H), 2.12 (s, 3H).





314
CF3


embedded image








315
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.42 (s, 1H), 7.29 (s, 1H), 6.94 (s, 1H), 5.78 (s, 1H), 4.21 (t, J = 7.0 Hz, 2H), 2.65 (t, J = 7.0 Hz, 2H).





316
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.74 (d, J = 1.0 Hz, 1H), 7.93-7.84 (m, 2H), 7.22 (d, J = 2.5 Hz, 1H), 7.13 (s, 1H), 6.63 (d, J = 2.5 Hz, 1H), 4.91 (s, 2H), 3.85 (s, 3H), 3.63 (s, 2H).





317
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.25 (s, 1H), 7.13 (s, 1H), 5.46 (s, 2H), 3.89 (hept, J = 6.5 Hz, 1H), 3.63 (s, 2H), 3.42 (q, J = 8.0 Hz, 2H), 2.66 (s, 3H), 1.20 (t, J = 8.0 Hz, 3H), 1.15 (d, J = 6.5 Hz, 6H).





318
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.26 (s, 1H), 8.37 (d, J = 8.0 Hz, 1H), 8.12 (d, J = 8.0 Hz, 1H), 7.31 (s, 1H), 5.33 (s, 1H), 3.48 (q, J = 8.0 Hz, 2H), 3.21-3.13 (m, 1H), 1.97-1.87 (m, 2H), 1.84-1.72 (m, 1H), 1.75-1.57 (m, 4H), 1.54- 1.42 (m, 2H), 1.45-1.37 (m, 1H), 1.23 (t, J = 8.0 Hz, 3H).





319
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.01 (s, 1H), 7.33 (s, 1H), 7.34-7.23 (m, 6H), 7.07 (s, 1H), 5.83 (s, 1H), 4.88 (s, 2H).





320
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.45 (d, J = 1.5 Hz, 1H), 8.59 (s, 1H), 8.52 (d, J = 1.5 Hz, 1H), 7.96-7.80 (m, 2H), 7.41- 7.34 (m, 4H), 7.31-7.26 (m, 2H), 4.59 (s, 1H).





321
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.68 (dd, J = 2.0, 1.5 Hz, 1H), 7.17 (s, 1H), 7.07 (s, 1H), 7.01 (dd, J = 1.5, 1.0 Hz, 1H), 6.94 (dd, J = 2.0, 1.0 Hz, 1H), 4.67 (s, 1H), 3.81 (s, 3H), 3.74 (s, 3H), 2.84 (s, 3H).





322
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.41 (d, J = 1.0 Hz, 1H), 8.68 (d, J = 1.0 Hz, 1H), 8.03 (s, 1H), 7.44 (d, J = 2.5 Hz, 1H), 7.36-7.30 (m, 2H), 6.61 (dd, J = 2.5, 2.0 Hz, 1H), 5.82 (s, 2H), 5.17 (s, 1H), 3.63 (s, 2H).





323
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.07 (d, J = 1.5 Hz, 1H), 8.38 (d, J = 8.0 Hz, 1H), 8.16 (dd, J = 8.0, 1.5 Hz, 1H), 7.30 (s, 1H), 6.64 (s, 1H), 5.29 (s, 1H), 5.32- 5.20 (hept, J = 6.5 Hz, 1H), 1.29 (d, J = 6.5 Hz, 6H).





324
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.74 (d, J = 1.0 Hz, 1H), 8.00 (d, J = 8.0 Hz, 1H), 7.92 (dd, J = 8.0, 1.0 Hz, 1H), 7.12 (s, 1H), 5.39 (s, 1H), 3.53 (s, 3H).





325
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.27 (d, J = 1.0 Hz, 1H), 7.87 (d, J = 1.0 Hz, 1H), 7.31 (s, 1H), 5.43 (s, 1H), 2.68 (s, 3H), 2.32-2.21 (m, 1H), 1.37-1.27 (m, 2H), 1.08-0.99 (m, 2H).





326
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.07 (s, 1H), 7.84 (s, 1H), 7.13 (s, 1H), 5.33 (s, 1H), 3.58 (s, 3H), 2.70 (s, 3H).





327
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.32 (s, 1H), 8.82 (d, J = 5.5 Hz, 1H), 8.76 (d, J = 5.5 Hz, 1H), 7.10 (s, 1H), 5.13 (s, 1H).





328
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.24 (s, 1H), 8.72 (s, 1H), 7.29 (s, 1H), 5.18 (s, 1H).





329
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.42 (s, 1H), 9.11 (s, 1H), 7.30 (s, 1H), 5.23 (s, 1H).





330
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.62 (d, J = 5.5 Hz, 1H), 8.34 (d, J = 5.5 Hz, 1H), 7.28 (s, 1H), 5.19 (s, 1H), 2.80 (s, 3H).





331
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.18 (s, 1H), 7.31 (s, 1H), 6.93 (s, 1H), 5.43 (s, 1H), 1.99-1.83 (m, 1H), 0.91-0.81 (m, 2H), 0.70-0.60 (m, 2H).





332
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.91 (s, 1H), 7.35 (s, 1H), 6.96-6.82 (m, 1H), 6.01-5.83 (m, 1H), 5.35 (s, 1H).





333
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.12 (s, 1H), 7.99 (s, 1H), 7.28 (s, 1H), 5.29 (s, 1H).





334
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.13 (s, 1H), 8.40 (s, 1H), 7.28 (s, 1H), 5.39 (s, 1H), 4.89 (hept, J = 6.5 Hz, 1H), 1.30 (d, J = 6.5 Hz, 6H).





335
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.35 (s, 1H), 7.25 (s, 1H), 5.91-5.80 (m, 1H), 5.70 (s, 1H), 4.34-4.28 (m, 2H).





336
CF3


embedded image








337
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.26 (s, 1H), 5.71 (s, 1H), 3.35 (s, 3H).





338
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.21 (s, 1H), 8.55 (s, 1H), 7.33 (s, 1H), 5.07 (s, 1H), 3.53 (q, J = 8.0 Hz, 2H), 2.97 (q, J = 8.0 Hz, 2H), 1.37 (t, J = 8.0 Hz, 3H), 1.20 (t, J = 8.0 Hz, 3H).





339
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.34 (s, 1H), 8.75 (s, 1H), 7.30-7.23 (m, 2H), 7.02-6.96 (m, 3H), 5.41 (s, 1H), 3.88 (s, 2H), 3.71 (s, 3H).





340
CF3


embedded image








341
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.50 (dd, J = 5.5, 1.5 Hz, 1H), 8.01 (dd, J = 7.5, 1.5 Hz, 1H), 7.82 (dd, J = 7.5, 5.5 Hz, 1H), 7.23 (s, 1H), 5.77 (s, 1H).





342
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.49 (d, J = 5.5 Hz, 1H), 7.88 (d, J = 5.5 Hz, 1H), 7.29 (s, 1H), 5.37 (s, 1H).





343
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.78 (d, J = 7.5 Hz, 1H), 8.38 (d, J = 7.5 Hz, 1H), 7.24 (s, 1H), 5.82 (s, 1H).





344
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.40 (d, J = 1.5 Hz, 1H), 7.94 (d, J = 1.5 Hz, 1H), 7.27 (s, 1H), 5.62 (s, 1H), 2.60 (t, J = 8.0 Hz, 2H), 1.54-1.31 (m, 4H), 0.89 (t, J = 7.5 Hz, 3H).





345
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.96 (d, J = 7.5 Hz, 1H), 7.77 (d, J = 7.5 Hz, 1H), 7.23 (s, 1H), 5.79 (s, 1H), 4.33-4.12 (m, 2H), 3.17-3.01 (m, 1H), 2.12-





1.88 (m, 2H), 1.39 (d, J = 6.5 Hz, 3H).





346
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.02 (d, J = 7.5 Hz, 1H), 7.69 (d, J = 7.5 Hz, 1H), 7.27 (s, 1H), 5.39 (s, 1H), 4.46-4.23 (m, 1H), 2.53-2.34 (m, 1H), 1.53- 1.29 (m, 1H).





347
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.31 (d, J = 1.5 Hz, 1H), 7.46 (d, J = 1.5 Hz, 1H), 7.25 (s, 1H), 5.93 (s, 1H), 5.49 (s, 1H).





348
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.99 (d, J = 7.5 Hz, 1H), 7.86 (d, J = 7.5 Hz, 1H), 7.27 (s, 1H), 5.63 (s, 1H), 5.17 (s, 1H).





349
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.04 (d, J = 7.5 Hz, 1H), 7.98 (d, J = 7.3 Hz, 1H), 7.26 (s, 1H), 5.44 (s, 1H), 3.35 (s, 1H).





350
CF3


embedded image








351
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.30 (s, 1H), 7.84 (s, 1H), 7.31 (s, 1H), 5.53 (s, 1H).





352
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.58 (s, 1H), 7.07 (s, 1H), 5.31 (s, 1H), 3.73 (s, 3H).





353
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.23 (s, 1H), 7.07 (s, 1H), 5.98-5.81 (m, 1H), 5.77 (s, 1H), 5.29-5.20 (m, 1H), 5.14- 5.03 (m, 1H), 4.90 (s, 1H), 3.99-3.83 (m, 2H), 3.76 (s, 3H).





354
CF3


embedded image








355
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.12 (d, J = 7.5 Hz, 1H), 7.48 (d, J = 7.5 Hz, 1H), 7.30-7.17 (m, 4H), 7.33 (s, 1H), 5.41 (s, 1H).





356
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.86 (d, J = 7.5 Hz, 1H), 7.28 (s, 1H), 7.06 (d, J = 7.5 Hz, 1H), 5.21 (s, 1H), 2.86 (s, 3H), 2.27 (q, J = 8.0 Hz, 2H), 1.12 (t, J = 8.0 Hz, 3H).





357
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.02 (d, J = 7.5 Hz, 1H), 7.85 (d, J = 7.5 Hz, 1H), 7.27 (s, 1H), 5.46 (s, 1H), 2.97 (q, J = 8.1 Hz, 2H), 1.37 (t, J = 8.0 Hz, 3H).





358
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.72 (d, J = 1.5 Hz, 1H), 9.43 (d, J = 5.5 Hz, 1H), 8.04 (dd, J = 5.5, 1.5 Hz, 1H), 7.24 (s, 1H), 5.86 (s, 1H).





359
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.61 (d, J = 1.5 Hz, 1H), 8.21 (d, J = 1.5 Hz, 1H), 7.26 (s, 1H), 5.87 (s, 1H).





360
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.48 (s, 1H), 9.42 (s, 1H), 7.27 (s, 1H), 5.60 (s, 1H), 2.36 (s, 3H).





361
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.58 (d, J = 1.5 Hz, 1H), 7.94 (d, J = 1.5 Hz, 1H), 7.28 (s, 1H), 5.54 (s, 1H), 4.47-4.37 (m, 2H), 2.75-2.34 (m, 2H).





362
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.35 (d, J = 6.0 Hz, 1H), 7.84 (d, J = 6.0 Hz, 1H), 7.27 (s, 1H), 5.73 (s, 1H), 2.38-2.22 (m, 1H), 0.85-0.74 (m, 2H), 0.73- 0.61 (m, 2H).





363
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.90 (s, 1H), 7.27 (s, 1H), 6.39-6.29 (m, 2H), 5.61 (s, 1H), 2.76 (s, 3H), 2.16 (d, J = 6.0 Hz, 3H).





364
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.99 (s, 1H), 7.72 (s, 1H), 7.37 (s, 1H), 5.37 (s, 1H).





365
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.57 (s, 1H), 6.95 (s, 1H).





366
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.53 (d, J = 1.5 Hz, 1H), 8.08 (d, J = 1.5 Hz, 1H), 7.24 (s, 1H), 5.86 (s, 1H), 3.78 (t, J = 7.5 Hz, 2H), 3.21 (t, J = 7.5 Hz, 2H).





367
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.63 (d, J = 1.5 Hz, 1H), 8.02 (d, J = 1.5 Hz, 1H), 7.46-7.29 (m, 3H), 7.23 (s, 1H), 5.80 (s, 1H), 3.88 (s, 2H).





368
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.03 (s, 1H), 7.37 (s, 1H), 6.50 (s, 1H), 3.27 (s, 6H), 2.97 (q, J = 8.0 Hz, 2H), 1.36 (t, J = 8.0 Hz, 3H).





369
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.95 (s, 1H), 7.26 (s, 1H), 5.43 (s, 1H), 4.34 (q, J = 8.0 Hz, 2H), 3.39 (s, 3H), 1.61 (t, J = 8.0 Hz, 3H).





370
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.27-8.06 (m, 2H), 8.04-7.94 (m, 2H), 7.84- 7.70 (m, 1H), 7.55-7.50 (m, 2H), 7.09 (s, 1H), 5.52 (s, 1H).





371
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.23-7.96 (m, 2H), 7.82-7.71 (m, 3H), 7.62- 6.51 (m, 1H), 7.09 (s, 1H), 5.47 (s, 1H).





372
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.18-7.93 (m, 2H), 7.69-7.55 (m, 2H), 7.23- 7.16 (m, 1H), 7.10 (s, 1H), 6.98-6.91 (m, 1H), 5.47 (s, 1H), 3.87 (s, 3H).





373
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.04-7.80 (m, 2H), 7.64-7.55 (m, 1H), 7.31- 7.26 (m, 2H), 7.14-7.09 (m, 2H), 5.52 (s, 1H), 3.87 (s, 3H).





374
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.76 (d, J = 1.5 Hz, 1H), 8.34-8.25 (m, 2H), 8.10- 7.90 (m, 2H), 7.05 (s, 1H), 6.77-6.51 (m, 1H), 5.76-5.65 (m, 2H), 5.25- 5.11 (m, 1H), 3.16 (s, 3H).





375
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.24-8.19 (m, 2H), 8.12 (d, J = 1.5 Hz, 1H), 7.87- 7.63 (m, 2H), 7.11 (s, 1H), 5.33 (s, 1H), 3.95 (s, 3H).





376
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.21-8.16 (m, 1H), 7.94-7.85 (m, 1H), 7.77- 7.55 (m, 2H), 7.42-7.31 (m, 2H), 7.09 (s, 1H), 5.52 (s, 1H), 1.94-1.82 (m, 1H), 1.23-1.14 (m, 2H), 0.96-0.87 (m, 2H).





377
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.63-8.51 (m, 1H), 8.06-7.99 (m, 2H), 7.90- 7.84 (m, 1H), 7.81-7.76 (m, 2H), 7.07 (s, 1H), 6.11 (s, 1H), 2.65 (s, 3H).





378
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.50 (s, 1H), 7.99-7.90 (m, 2H), 7.89-7.81 (m, 1H), 7.67-7.47 (m, 3H), 7.03 (s, 1H), 5.43 (s, 1H), 2.22 (s, 3H).





379
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.20-7.95 (m, 2H), 7.87-7.81 (m, 1H), 7.78- 7.64 (m, 3H), 7.10 (s, 1H), 5.48 (s, 1H), 3.78 (t, J = 7.5 Hz, 2H), 3.07 (t, J = 7.5 Hz, 2H).





380
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.11-8.01 (m, 2H), 7.99-7.87 (m, 1H), 7.92- 7.78 (m, 2H), 7.53-7.47 (m, 2H), 7.09 (s, 1H), 5.63 (s, 1H).





381
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.79-7.57 (m, 3H), 7.56 (d, J = 1.5 Hz, 1H), 7.20- 7.13 (m, 2H), 7.08 (s, 1H), 5.55 (s, 1H), 5.00 (s, 1H), 2.82 (s, 3H).





382
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.11-8.02 (m, 2H), 8.00-7.90 (m, 2H), 7.78- 7.65 (m, 2H), 7.50 (t, J = 73.5 Hz, 2H), 7.09 (s, 1H), 5.55 (s, 1H).





383
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.03-7.93 (m, 2H), 7.92-7.83 (m, 2H), 7.46- 7.38 (m, 2H), 7.09 (s, 1H), 5.61 (s, 1H), 2.50 (s, 3H).





384
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.13-8.02 (m, 2H), 7.89-7.77 (m, 2H), 7.65- 7.52 (m, 2H), 7.10 (s, 1H), 5.51 (s, 1H).





385
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.12-8.04 (m, 2H), 7.87-7.62 (d, J = 8.0 Hz, 4H), 7.07 (s, 1H), 5.26 (s, 1H).





386
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.57 (d, J = 1.5 Hz, 1H), 8.10-8.02 (m, 3H), 7.99- 7.81 (m, 2H), 7.09 (s, 1H), 6.26 (d, J = 72.5 Hz 1H), 5.53 (s, 1H).





387
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.33-8.23 (m, 2H), 8.09-7.98 (m, 2H), 7.10 (s, 1H), 6.34-6.22 (m, 1H), 5.50 (s, 1H), 3.95 (s, 3H), 3.90 (s, 3H).





388
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.11-8.00 (m, 2H), 7.91-7.78 (m, 2H), 7.47- 7.37 (m, 2H), 7.05 (s, 1H), 5.51 (s, 1H), 3.51 (t, J = 7.5 Hz, 2H), 3.23 (s, 3H), 2.43 (t, J = 7.5 Hz, 2H).





389
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.15-8.03 (m, 1H), 7.87-7.78 (m, 2H), 7.61- 7.44 (m, 2H), 7.10-7.01 (m, 2H), 6.12 (s, 2H), 5.52 (s, 1H), 3.29 (s, 3H).





390
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.42 (s, 1H), 8.27 (d, J = 1.5 Hz, 1H), 7.92 (d, J = 7.5 Hz, 1H), 7.50 (dd, J = 7.5, 1.5 Hz, 1H), 7.04 (s, 1H), 5.63 (s, 1H), 3.18 (s, 3H), 3.03-2.98 (m, 2H), 2.68 (s, 3H), 2.16-2.06 (m, 1H), 1.44-1.33 (m, 1H), 0.99-0.84 (m, 2H).





391
CF3


embedded image








392
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.31 (d, J = 7.5 Hz, 1H), 8.10 (d, J = 7.5 Hz, 1H), 7.84-7.70 (m, 3H), 7.54-7.42 (m, 1H), 7.09 (s, 1H), 5.63 (s, 1H), 3.70 (s, 2H), 2.27 (s, 3H).





393
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.82-7.73 (m, 1H), 7.67-7.60 (m, 2H), 7.19 (d, J = 1.5 Hz, 1H), 7.07 (s, 1H), 5.40 (s, 1H), 3.81 (s, 2H), 2.52 (s, 3H), 2.35 (s, 3H), 2.27 (s, 3H).





394
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.30-8.13 (m, 2H), 7.85-7.76 (m, 2H), 7.69- 7.62 (m, 2H), 7.09 (s, 1H), 5.43 (s, 1H), 4.53 (s, 2H), 3.95 (s, 2H), 3.28 (s, 3H).





395
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.42-8.37 (m, 1H), 7.54 (d, J = 1.5 Hz, 1H), 7.47- 7.36 (m, 2H), 7.04 (s, 1H), 6.88-6.69 (m, 1H), 5.71 (s, 1H), 4.96 (s, 2H), 3.90 (s, 3H).





396
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.38 (d, J = 1.5 Hz, 1H), 8.18 (dd, J = 7.5, 1.5 Hz, 1H), 8.12-8.01 (m, 2H), 7.88-7.62 (m, 2H), 7.07 (s, 1H), 5.55 (s, 1H), 2.42 (s, 3H).





397
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.05-7.97 (m, 1H), 8.00-7.91 (m, 2H), 7.76- 7.68 (m, 2H), 7.58-7.42 (m, 1H), 7.08 (s, 1H), 5.57 (s, 1H), 3.82 (s, 2H), 1.85 (s, 3H).





398
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.99-7.93 (m, 2H), 7.83-7.53 (m, 2H), 7.40- 7.24 (m, 2H), 7.09 (s, 1H), 5.49 (d, J = 73.5 Hz, 1H), 5.20 (s, 1H).





399
CF3


embedded image








400
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.43-8.34 (m, 2H), 7.99-7.82 (m, 2H), 7.73- 7.66 (m, 1H), 7.09 (s, 1H), 6.24-6.12 (m, 1H), 5.57 (s, 1H), 5.10 (s, 2H), 2.20 (s, 3H).





401
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.00-7.88 (m, 2H), 7.91-7.70 (m, 2H), 7.51- 7.39 (m, 1H), 7.11-7.05 (m, 2H), 5.62 (s, 1H), 4.93 (s, 2H), 3.73 (s, 3H).





402
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.69-8.42 (m, 2H), 8.11-8.00 (m, 2H), 7.78- 7.53 (m, 2H), 7.50-7.42 (m, 2H), 7.12- 7.03 (m, 3H), 5.71 (s, 1H), 3.94 (hept, J = 6.5 Hz, 1H), 1.52 (d, J = 6.5 Hz, 6H).





403
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.71-8.63 (m, 1H), 8.34-8.20 (m, 2H), 8.13- 8.04 (m, 2H), 7.88-7.79 (m, 1H), 7.10 (s, 1H), 5.72-5.50 (m, 1H), 5.44 (s, 1H), 4.48 (s, 2H), 2.72-2.50 (m, 2H), 2.39 (s, 3H).





404
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.11-8.06 (m, 2H), 7.73-7.64 (m, 2H), 7.51- 7.37 (m, 2H), 7.09 (s, 1H), 5.61 (s, 1H), 4.48 (s, 2H), 3.34 (s, 3H).





405
CF3


embedded image








406
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.06 (s, 1H), 7.74-7.64 (m, 2H), 7.42-7.29 (m, 2H), 7.09 (s, 1H), 5.64 (s, 1H), 5.24 (s, 2H), 5.00 (s, 2H), 4.27 (s, 2H), 3.70 (hept, J = 6.5 Hz, 1H), 3.10 (q, J = 8.0 Hz, 2H), 1.35 (t, J = 8.0 Hz, 3H), 1.02 (d, J = 6.5 Hz, 6H).





407
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.05-7.98 (m, 2H), 7.79-7.72 (m, 2H), 7.50- 7.43 (m, 2H), 7.31 (s, 1H), 5.41 (s, 1H), 5.11 (s, 2H), 2.86 (s, 3H).





408
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.88 (d, J = 7.5 Hz, 1H), 7.72-7.64 (m, 2H), 7.63 (d, J = 7.5 Hz, 1H), 7.56 (d, J = 7.5 Hz, 1H), 7.09 (s, 1H), 5.51 (s, 1H), 3.81 (s, 2H), 3.64-3.47 (m, 1H), 2.94 (s, 3H), 1.83-1.71 (m, 3H), 1.71-1.57 (m, 2H), 1.57-1.37 (m, 5H).





409
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.68-7.55 (m, 2H), 7.41-7.31 (m, 3H), 7.28- 7.19 (m, 1H), 7.09 (s, 1H), 6.06 (s, 2H), 5.55 (s, 1H), 3.45 (q, J = 8.0 Hz, 2H), 1.22 (t, J = 8.0 Hz, 3H).





410
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.10-8.00 (m, 2H), 7.94-7.81 (m, 1H), 7.79- 7.65 (m, 2H), 7.49-7.33 (m, 1H), 7.09 (s, 1H), 5.56 (s, 1H), 5.11 (s, 2H), 4.67 (s, 2H), 2.59 (q, J = 8.0 Hz, 2H), 1.29 (s, 1H), 1.02 (t, J = 8.0 Hz, 3H).





411
CF3


embedded image








412
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.18 (d, J = 1.5 Hz, 1H), 8.02 (dd, J = 7.5, 1.5 Hz, 1H), 7.85-7.77 (m, 2H), 7.53-7.43 (m, 2H), 7.10 (s, 1H), 5.41 (s, 1H), 4.27 (s, 2H), 2.56 (s, 3H).





413
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.83 (dd, J = 2.5 Hz, 1H), 7.17 (d, J = 2.0 Hz, 2H), 6.80 (dd, J = 2.5, 2.0 Hz, 1H).





414
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.18 (s, 1H), 6.90 (d, J = 2.5 Hz, 1H), 6.11 (d, J = 2.5 Hz, 1H), 2.36 (s, 3H).





415
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.40 (s, 1H), 7.20 (s, 1H), 6.30 (s, 1H), 6.00 (s, 1H), 2.94 (hept, J = 6.5 Hz, 1H), 1.52 (d, J = 6.5 Hz, 6H).





416
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.35 (d, J = 2.5 Hz, 1H), 7.18 (s, 1H), 6.45 (d, J = 2.5 Hz, 1H), 2.66 (q, J = 8.0 Hz, 2H), 1.30 (t, J = 8.0 Hz, 3H).





417
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.40 (d, J = 9.0 Hz, 1H), 7.20 (s, 1H), 6.30 (d, J = 8.5 Hz, 1H), 6.00 (s, 1H).





418
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.50 (s, 1H), 7.18 (s, 1H), 6.67 (s, 1H), 5.64 (s, 1H).





419
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.45 (d, J = 2.5 Hz, 1H), 7.15 (s, 1H), 6.76 (d, J = 2.5 Hz, 1H), 5.84 (s, 1H).





420
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.18 (s, 1H), 6.85 (d, J = 2.5 Hz, 1H), 5.80 (d, J = 2.5 Hz, 1H), 3.85 (s, 3H).





421
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.29 (d, J = 2.5 Hz, 1H), 7.20 (s, 1H), 7.06 (d, J = 2.5 Hz, 1H), 5.67 (s, 1H).





422
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.43 (d, J = 2.5 Hz, 1H), 7.30 (d, J = 2.5 Hz, 1H), 7.17 (s, 1H), 5.77 (s, 1H).





423
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 10.38 (s, 1H), 7.71 (d, J = 1.5 Hz, 1H), 7.47 (d, J = 1.5 Hz, 1H), 7.13 (s, 1H), 6.43 (s, 1H).






424
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.20 (d, J = 2.5 Hz, 1H), 7.15 (s, 1H), 6.42 (d, J = 2.5 Hz, 1H), 5.81 (s, 1H), 2.37 (s, 3H).





425
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.63 (s, 1H), 7.15 (s, 1H), 6.09 (s, 1H), 5.87 (s, 1H), 2.38 (t, J = 6.5 Hz, 2H), 1.86- 1.71 (m, 2H), 1.00 (t, J = 8.0 Hz, 3H).





426
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.34 (s, 1H), 7.27 (s, 1H), 7.20 (s, 1H), 6.07 (s, 1H), 1.30 (s, 9H).





427
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.30 (d, J = 2.5 Hz, 1H), 7.16 (s, 1H), 6.32 (d, J = 2.5 Hz, 1H), 5.74 (s, 1H).





428
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.40 (s, 1H), 7.20 (s, 1H), 6.30 (d, J = 8.0 Hz, 1H), 6.00 (s, 1H).





429
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.60 (s, 1H), 7.53 (s, 1H), 7.24 (s, 1H), 5.52 (s, 1H).





430
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.99 (s, 1H), 8.25 (s, 1H), 7.20 (s, 1H), 6.90 (d, J = 7.5 Hz, 1H), 6.11 (d, J = 7.5 Hz, 1H), 2.87 (s, 3H).





431
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.59 (s, 1H), 7.15 (s, 1H), 6.40 (s, 1H), 5.88 (s, 1H), 2.43 (s, 3H).





432
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.24 (s, 1H), 7.20 (s, 1H), 7.10 (s, 1H), 6.00 (s, 1H), 1.50-1.37 (m, 1H), 1.12-1.02 (m, 2H), 0.82-0.72 (m, 2H).





433
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.18 (s, 1H), 6.70 (s, 1H), 6.44 (s, 1H), 5.87 (s, 1H), 5.66 (s, 1H).





434
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.40 (s, 1H), 7.73 (s, 1H), 7.19 (s, 1H).





435
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.15 (s, 1H), 6.86 (d, J = 2.5 Hz, 1H), 6.17 (d, J = 2.5 Hz, 1H).





436
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.29 (d, J = 2.5 Hz, 1H), 7.23-7.18 (m, 2H), 3.91 (s, 3H).





437
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.47 (d, J = 2.5 Hz, 1H), 7.16 (s, 1H), 6.49 (d, J = 2.5 Hz, 1H), 2.99 (s, 6H).





438
CF3


embedded image








439
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.17 (s, 1H), 6.04 (s, 1H), 2.36 (s, 3H), 2.26 (s, 3H).





440
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.56 (s, 1H), 7.18 (s, 1H), 7.06 (s, 1H), 6.83- 6.67 (m, 1H), 5.67-5.46 (m, 2H).





441
CF3


embedded image



1H NMR (500 MHz, Chloroform-d) δ 7.17 (s, 1H), 6.57 (s, 1H), 5.32 (s, 1H), 2.19 (s, 3H).






442
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.17 (s, 1H), 2.32 (s, 3H), 2.19 (s, 3H), 2.05 (s, 3H).





443
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.27 (d, J = 2.5 Hz, 1H), 7.15 (s, 1H), 6.37 (d, J = 2.5 Hz, 1H), 5.78 (s, 1H), 4.48 (s, 2H), 3.38 (s, 3H).





444
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.27 (s, 1H), 7.15 (s, 1H), 5.78 (s, 1H), 3.88 (q, J = 8.0 Hz, 2H), 3.08 (s, 3H), 1.48 (t, J = 8.0 Hz, 3H).





445
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.64 (s, 1H), 7.26 (s, 1H), 7.19 (s, 1H), 6.09- 6.00 (m, 1H), 5.74 (s, 1H), 2.95-2.89 (m, 2H).





446
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.16 (s, 1H), 5.73 (s, 1H), 2.30 (s, 3H), 2.24 (s, 3H), 2.05 (s, 3H).





447
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.40 (s, 1H), 7.20 (s, 1H), 6.00 (s, 1H).





448
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.21 (s, 2H), 5.97 (s, 1H), 2.31 (s, 3H), 2.05 (s, 3H).





449
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.78 (s, 1H), 7.64 (d, J = 2.5 Hz, 1H), 7.43 (s, 1H), 6.56 (d, J = 2.5 Hz, 1H), 3.16 (s, 3H).





450
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.17 (s, 1H), 7.05 (s, 1H), 5.74 (s, 1H), 5.39 (s, 1H), 2.34 (s, 3H).





451
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.50 (s, 1H), 8.34 (s, 1H), 7.66 (s, 1H), 7.44 (s, 1H), 2.55 (s, 3H).





452
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.69 (s, 1H), 7.25-7.17 (m, 2H), 7.09 (d, J = 2.5 Hz, 1H).





453
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.99 (s, 1H), 7.50 (s, 1H), 7.21 (s, 1H), 6.41 (s, 1H), 3.01 (s, 1H).





454
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.56-7.44 (m, 2H), 7.24-7.17 (m, 2H).





455
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.05 (s, 1H), 7.66 (d, J = 2.5 Hz, 1H), 7.12 (d, J = 2.5 Hz, 1H), 6.88 (s, 1H), 2.40 (s, 3H).






456
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.46 (s, 1H), 7.20 (s, 2H), 7.09 (s, 1H), 2.30 (s, 3H).





457
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.46 (s, 1H), 7.19 (s, 1H), 7.09 (s, 1H), 2.71 (q, J = 8.0 Hz, 2H), 1.26 (t, J = 8.0 Hz, 3H).





458
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.46 (d, J = 2.5 Hz, 1H), 7.19 (s, 1H), 7.09 (d, J = 2.5 Hz, 1H), 2.71 (hept, J = 8.0 Hz, 1H), 1.26 (d, J = 8.0 Hz, 6H).





459
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.24 (d, J = 2.5 Hz, 1H), 7.15 (s, 1H), 6.29 (d, J = 2.5 Hz, 1H), 5.74 (s, 1H), 3.85 (s, 3H).





460
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.60 (s, 1H), 7.34 (s, 1H), 7.09 (s, 1H), 2.41 (s, 3H).





461
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.52 (d, J = 2.5 Hz, 1H), 7.33 (d, J = 2.5 Hz, 1H), 7.17 (s, 1H), 5.75 (s, 1H).





462
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.22-7.13 (m, 2H), 6.72-6.57 (m, 1H), 6.00 (s, 1H).





463
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.94 (s, 1H), 7.38 (s, 1H), 7.20 (s, 1H), 7.10 (s, 1H).





464
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.61 (d, J = 2.5 Hz, 1H), 7.46 (d, J = 2.5 Hz, 1H), 7.18 (s, 1H), 5.85 (s, 1H).





465
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.42 (d, J = 2.5 Hz, 1H), 7.36 (s, 1H), 7.20 (d, J = 2.5 Hz, 1H), 7.19 (s, 1H), 5.74 (s, 1H).





466
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.33 (d, J = 2.5 Hz, 1H), 7.16 (s, 1H), 7.08 (d, J = 2.5 Hz, 1H), 6.00 (s, 1H), 2.86 (q, J = 8.0 Hz, 2H), 1.32 (t, J = 8.0 Hz, 3H).





467
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.56 (s, 1H), 7.18 (s, 1H), 6.92 (s, 1H), 5.74 (s, 1H), 2.61 (t, J = 7.5 Hz, 2H), 1.51-1.37 (m, 4H), 0.96 (t, J = 7.5 Hz, 3H).





468
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.41 (s, 1H), 7.13 (s, 1H), 7.03 (s, 1H), 5.74 (s, 1H), 2.65 (t, J = 7.5 Hz, 2H), 1.74- 1.61 (m, 2H), 0.99 (t, J = 8.0 Hz, 3H).





469
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.93 (d, J = 2.5 Hz, 1H), 7.33 (d, J = 2.5 Hz, 1H), 7.11 (s, 1H), 5.65 (s, 1H).





470
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.18 (s, 1H), 6.32 (s, 1H), 6.27 (s, 1H), 5.95 (s, 1H), 5.84 (s, 1H).





471
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.85 (s, 1H), 7.56 (s, 1H), 7.17 (s, 1H), 5.69 (s, 1H).





472
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.68 (d, J = 2.5 Hz, 1H), 7.31 (d, J = 2.5 Hz, 1H), 7.15 (s, 1H), 5.75 (s, 1H), 4.31 (q, J = 7.0 Hz, 2H), 1.33 (t, J = 7.0 Hz, 3H).





473
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.16 (s, 1H), 8.50 (s, 1H), 7.13 (s, 1H), 5.86 (s, 1H), 3.45 (q, J = 6.5 Hz, 2H), 1.43 (t, J = 6.5 Hz, 3H).





474
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.87 (s, 1H), 8.30 (s, 1H), 7.84 (s, 1H), 7.14 (s, 1H), 5.93 (s, 1H).





475
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.80 (d, J = 2.5 Hz, 1H), 7.73 (d, J = 2.5 Hz, 1H), 7.17 (s, 1H), 5.90 (s, 1H), 2.51 (s, 3H).





476
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.69 (s, 1H), 7.17 (s, 1H), 6.30-6.23 (m, 1H), 6.19 (s, 1H), 6.10-6.01 (m, 1H), 1.70 (d, J = 6.5 Hz, 3H).





477
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.50 (s, 1H), 7.20 (s, 1H), 7.07 (s, 1H).





478
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.20 (s, 1H), 6.63 (d, J = 7.5 Hz, 1H), 6.00 (s, 1H), 2.23 (s, 3H).





479
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.92 (s, 1H), 7.20 (s, 1H), 6.64 (s, 1H), 2.40 (s, 3H).





480
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.19 (s, 1H), 6.70 (s, 1H), 2.46 (s, 3H), 2.36 (s, 3H), 2.30 (s, 3H).





481
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.20 (s, 1H), 6.00 (s, 1H), 2.44 (s, 3H), 2.24 (s, 3H).





482
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.22 (d, J = 2.5 Hz, 1H), 7.71 (d, J = 2.5 Hz, 1H), 7.21 (s, 1H), 7.15 (s, 1H).





483
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.20 (s, 1H), 7.10 (s, 1H), 6.86 (s, 1H), 6.05 (s, 1H), 3.26 (q, J = 8.0 Hz, 2H), 2.98 (s, 3H), 1.19 (t, J = 8.0 Hz, 3H).





484
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.60 (s, 1H), 7.85 (d, J = 2.5 Hz, 1H), 7.76 (d, J = 2.5 Hz, 1H), 7.37 (s, 1H), 3.15 (s, 3H).





485
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.50 (s, 1H), 7.20 (s, 1H), 7.15 (s, 1H), 2.52 (s, 3H).





486
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.25 (s, 1H), 7.22-7.16 (m, 2H), 6.55 (s, 1H), 4.46 (q, J = 9.5 Hz, 2H).





487
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.25 (s, 1H), 7.22 (s, 1H), 6.55 (s, 1H), 2.31 (s, 3H), 2.21 (s, 3H).





488
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.13 (s, 1H), 6.19 (s, 1H), 5.72 (s, 1H), 3.52 (s, 1H).





489
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.13 (s, 1H), 6.84 (s, 1H), 5.65 (s, 1H), 2.71 (q, J = 8.0 Hz, 2H), 2.41 (s, 3H), 1.26 (t, J = 8.0 Hz, 3H).





490
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.13 (s, 1H), 5.68 (s, 1H), 3.52 (s, 1H), 2.40 (s, 3H), 2.30 (s, 3H), 2.26 (s, 3H).





491
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.13 (s, 1H), 5.68 (s, 1H), 2.40 (d, J = 7.1 Hz, 6H), 2.26 (s, 3H).





492
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.03 (s, 1H), 7.21 (s, 1H), 7.13 (s, 1H), 6.00 (s, 1H), 1.50-1.41 (m, 1H), 0.91-0.79 (m, 4H).





493
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.33 (s, 1H), 7.24 (s, 1H), 7.14 (s, 1H), 6.00 (s, 1H), 2.32-2.22 (m, 1H), 2.04-1.91 (m, 4H), 1.78-1.62 (m, 6H).





494
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.38 (d, J = 2.5 Hz, 1H), 7.18 (s, 1H), 5.47 (d, J = 2.5 Hz, 1H), 5.30 (s, 1H), 2.21 (s, 3H).





495
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.16 (s, 1H), 6.88 (s, 1H), 5.97 (s, 1H), 3.31 (hept, J = 6.5 Hz, 1H), 2.37 (s, 3H), 1.30 (d, J = 6.5 Hz, 6H).





496
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.18 (s, 1H), 7.06 (s, 1H), 5.88 (s, 1H), 3.50 (s, 2H), 2.46 (s, 3H).





497
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ11.71 (s, 1H), 8.13 (s, 1H), 7.76 (s, 1H), 6.88 (s, 1H).






498
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.35 (s, 1H), 7.20 (s, 1H), 6.98 (s, 1H), 2.77 (s, 3H).





499
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.98 (s, 1H), 7.35 (s, 1H), 7.20 (s, 1H).





500
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.43 (s, 1H), 7.20 (s, 1H), 6.82 (s, 1H), 4.00 (s, 3H).





501
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 10.60 (s, 1H), 8.11 (d, J = 2.5 Hz, 1H), 7.37 (d, J = 2.5 Hz, 1H), 6.89 (s, 1H).






502
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.12 (s, 1H), 5.79 (s, 1H), 2.46 (s, 3H).





503
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ11.73 (s, 1H), 9.42 (s, 1H), 6.84 (s, 1H).






504
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 9.12 (s, 1H), 6.89 (s, 1H), 3.79 (s, 3H).






505
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.12 (s, 1H), 5.71 (s, 1H).





506
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.35 (s, 1H), 7.10 (s, 1H).





507
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.11 (s, 1H), 7.18 (s, 1H).





508
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.34 (s, 1H), 8.23 (s, 1H), 6.82 (s, 1H).






509
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.19 (s, 1H), 8.30 (s, 1H), 6.79 (s, 1H).






510
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.44 (s, 1H), 7.17 (s, 1H).





511
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.15 (s, 1H), 5.75 (s, 1H), 2.54 (s, 3H), 2.49 (s, 3H).





512
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.67 (s, 1H), 9.20 (s, 1H), 8.10 (s, 1H), 6.88 (s, 1H).






513
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.85 (s, 1H), 7.30 (s, 1H), 7.18 (s, 1H).





514
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.38 1H), 8.18 (s, 1H), 8.10 (s, 1H), 7.12, 1H).






515
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.01 (s, 1H), 8.72 (s, 1H), 7.89 (s, 1H), 6.94 (s, 1H).






516
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.14 (s, 1H), 7.08 (s, 1H).





517
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.32 (s, 1H), 7.11 (s, 1H), 5.77 (s, 1H).





518
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.19 (s, 1H), 2.54 (s, 3H).





519
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.59 (s, 1H), 8.19 (s, 1H), 6.84 (s, 1H).






520
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.73 (s, 1H), 9.49 (s, 1H), 6.82 (s, 1H).






521
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.16 (s, 1H), 2.68 (s, 3H).





522
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.88 (s, 1H), 7.92 (d, J = 2.5 Hz, 1H), 7.37 (d, J = 2.5 Hz, 1H), 6.87 (s, 1H).






523
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.20 (s, 1H), 6.89 (d, J = 7.5 Hz, 1H), 6.00 (s, 1H).





524
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.31 (s, 1H), 7.19 (s, 1H).





525
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.74 (d, J = 2.5 Hz, 1H), 7.26 (d, J = 2.5 Hz, 1H), 6.88 (s, 1H).






526
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.47 (s, 1H), 8.72 (d, J = 2.0 Hz, 1H), 7.40 (d, J = 2.0 Hz, 1H), 6.85 (s, 1H).






527
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.48 (s, 2H), 7.07 (s, 1H), 5.93 (s, 1H).





528
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.58 (s, 1H), 8.37 (s, 1H), 7.10 (s, 1H), 5.93 (s, 1H).





529
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.75 (d, J = 2.5 Hz, 1H), 7.15 (s, 1H), 6.76 (d, J = 2.5 Hz, 1H), 5.95 (s, 1H).





530
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.41 (s, 1H), 8.81 (d, J = 2.5 Hz, 1H), 8.04 (s, 1H), 7.69 (d, J = 2.5 Hz, 1H), 6.74 (s, 1H).






531
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.29 (s, 2H), 7.22 (s, 1H).





532
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.33 (d, J = 2.5 Hz, 1H), 7.18 (s, 1H), 6.77 (d, J = 2.5 Hz, 1H).





533
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.88 (d, J = 2.5 Hz, 1H), 7.53 (d, J = 2.0 Hz, 1H), 7.26 (s, 1H), 6.62 (dd, J = 2.5, 2.0 Hz, 1H), 5.93 (s, 1H).





534
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.15 (s, 1H), 2.34 (s, 3H), 2.28 (s, 3H).





535
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.55 (s, 1H), 7.17 (s, 1H), 4.01 (s, 3H).





536
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.19 (s, 1H), 7.15 (s, 1H), 2.17 (s, 3H).





537
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.44 (s, 1H), 7.36 (s, 1H), 7.27 (s, 1H), 5.93 (s, 1H).





538
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.48 (s, 1H), 7.15 (s, 1H), 2.66 (q, J = 8.0 Hz, 2H), 1.30 (t, J = 8.0 Hz, 3H).





539
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.47 (s, 1H), 7.15 (s, 1H), 2.60 (s, 3H).





540
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.18 (s, 1H), 6.42 (s, 1H), 3.86 (s, 3H), 2.35 (s, 3H).





541
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.51 (d, J = 2.5 Hz, 1H), 7.26 (s, 1H), 6.13 (d, J = 2.5 Hz, 1H), 5.93 (s, 1H), 2.38 (s, 3H).





542
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.16 (s, 1H), 7.05 (s, 1H).





543
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.21 (s, 1H), 2.56 (s, 6H).





544
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.18 (s, 1H), 2.22 (s, 3H), 2.12 (s, 3H).





545
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.26 (s, 1H), 6.07 (s, 1H), 5.93 (s, 1H), 2.40 (s, 3H), 1.75 (s, 3H).





546
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.03 (s, 1H), 8.55 (s, 1H), 8.23 (s, 1H), 7.47 (s, 1H), 4.17 (t, J = 6.5 Hz, 2H), 1.83- 1.66 (m, 2H), 0.85 (t, J = 7.5 Hz, 3H).






547
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.15 (s, 1H), 7.01-6.81 (m, 2H), 6.37-6.23 (m, 1H), 5.92 (s, 1H).





548
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.18 (s, 1H), 7.15 (s, 1H), 7.07 (s, 1H), 6.88 (d, J = 2.5 Hz, 1H), 6.33 (d, J = 2.5 Hz, 1H), 5.81 (s, 1H).





549
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.33-7.21 (m, 2H), 7.13 (s, 1H), 6.33-6.21 (m, 2H), 5.93 (s, 1H).





550
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.80 (s, 1H), 7.19 (s, 1H), 7.05 (d, J = 2.5 Hz, 1H), 6.55 (d, J = 2.5 Hz, 1H), 5.39 (s, 1H).





551
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.07 (s, 1H), 7.20 (s, 1H), 6.74 (s, 1H), 6.66 (s, 1H), 6.00 (s, 1H), 2.15 (s, 3H).





552
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.37 (d, J = 2.5 Hz, 1H), 7.13 (s, 1H), 6.43 (s, 1H), 5.93 (s, 1H), 5.82 (d, J = 2.5 Hz, 1H), 3.85 (s, 3H).





553
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.19 (s, 1H), 6.45 (s, 1H), 6.32-6.26 (m, 2H), 3.71 (s, 3H), 2.63 (q, J = 8.0 Hz, 2H), 1.25 (t, J = 8.0 Hz, 3H).





554
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.92 (s, 1H), 7.21 (s, 1H), 6.58 (s, 1H), 5.94 (s, 1H), 5.86 (s, 1H), 2.30 (s, 3H).





555
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.24 (s, 1H), 6.94 (d, J = 2.5 Hz, 1H), 6.24 (dd, J = 2.5, 2.0 Hz, 1H), 6.09 (d, J = 2.0 Hz, 1H), 5.93 (s, 1H), 2.21 (s, 3H).





556
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.50 (s, 1H), 7.22 (s, 1H), 6.54 (d, J = 2.5 Hz, 1H), 6.00 (d, J = 2.5 Hz, 1H), 5.74 (s, 1H), 2.33 (s, 3H).





557
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.87 (s, 1H), 7.19 (s, 1H), 6.67 (d, J = 2.5 Hz, 1H), 6.18 (s, 1H), 6.05 (d, J = 2.5 Hz, 1H), 2.42 (s, 3H).





558
CF3


embedded image








559
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.53 (s, 1H), 8.99-8.88 (m, 2H), 7.29 (s, 1H).





560
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.61 (s, 1H), 9.55 (s, 1H), 9.41 (s, 1H), 7.28 (s, 1H), 5.74 (s, 1H).





561
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.55 (s, 1H), 8.63 (s, 1H), 7.36 (s, 1H).





562
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.39 (d, J = 1.5 Hz, 1H), 9.23 (d, J = 1.5 Hz, 1H), 8.57 (s, 1H), 7.28 (s, 1H), 5.94 (s, 1H).





563
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.99 (s, 1H), 8.78 (s, 1H), 7.87 (s, 1H), 7.29 (s, 1H), 5.54 (s, 1H).





564
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.23 (d, J = 1.5 Hz, 1H), 7.84 (d, J = 1.5 Hz, 1H), 7.53 (d, J = 2.5 Hz, 1H), 7.28 (s, 1H), 7.22 (d, J = 2.5 Hz, 1H), 5.92 (s, 1H).





565
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.61 (s, 1H), 9.55 (s, 1H), 9.42 (s, 1H), 7.28 (s, 1H), 5.74 (s, 1H).





566
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.53 (s, 1H), 8.99-8.88 (m, 2H), 7.29 (s, 1H), 5.34 (s, 1H).





567
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.35 (s, 1H), 8.25 (s, 1H), 7.25 (s, 1H).





568
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.75 (q, J = 1.5 Hz, 1H), 8.35 (q, J = 1.5 Hz, 1H), 7.28 (s, 1H), 2.39 (s, 3H).





569
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.84 (s, 1H), 8.75 (d, J = 5.5 Hz, 1H), 7.56 (d, J = 5.5 Hz, 1H), 7.28 (s, 1H).





570
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.91 (dd, J = 5.5, 1.5 Hz, 1H), 7.70 (dd, J = 7.5, 5.5 Hz, 1H), 7.49 (dd, J = 7.5, 1.5 Hz, 1H), 7.43 (s, 1H), 7.28 (s, 1H).





571
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.45-8.36 (m, 3H), 8.24-8.01 (m, 3H), 7.89- 7.79 (m, 1H), 7.54-7.45 (m, 2H), 7.10 (s, 1H), 5.56 (s, 1H).





572
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.95-8.91 (m, 1H), 8.59-8.55 (m, 1H), 8.37- 8.30 (m, 1H), 8.22-8.12 (m, 2H), 7.92- 7.74 (m, 3H), 7.11 (s, 1H), 5.55 (s, 1H).





573
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.86-8.31 (m, 3H), 8.04-7.90 (m, 3H), 7.75- 7.68 (m, 2H), 7.63-7.55 (m, 1H), 7.10 (s, 1H), 5.52 (s, 1H).





574
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.08-8.84 (m, 1H), 8.12-7.91 (m, 4H), 7.74- 7.58 (m, 4H), 7.10 (s, 1H), 5.66 (s, 1H).





575
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.90-8.84 (m, 2H), 8.58-8.37 (m, 2H), 7.91- 7.80 (m, 2H), 7.68-7.63 (m, 2H), 7.10 (s, 1H), 5.61 (s, 1H).





576
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.51 (d, J = 2.0 Hz, 1H), 8.32-8.26 (m, 3H), 7.89- 7.80 (m, 3H), 7.03 (s, 1H), 5.87 (s, 1H).





577
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.43 (d, J = 2.0 Hz, 1H), 8.26-8.06 (m, 2H), 7.95- 7.90 (m, 1H), 7.45-7.39 (m, 2H), 7.08 (s, 1H), 5.71 (s, 1H), 2.30 (s, 3H).





578
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.55-8.45 (m, 2H), 8.27-8.20 (m, 2H), 8.11- 7.97 (m, 2H), 7.72-7.54 (m, 2H), 7.10 (s, 1H), 5.50 (s, 1H).





579
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.61 (d, J = 1.5 Hz, 1H), 8.39 (d, J = 7.5 Hz, 1H), 8.14-8.10 (m, 3H), 7.80-7.67 (m, 2H), 7.05 (s, 1H), 5.75 (s, 1H).





580
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.42-9.13 (m, 2H), 8.59-8.49 (m, 2H), 7.97- 7.88 (m, 2H), 7.68-7.56 (m, 1H), 7.28 (s, 1H), 5.76 (s, 1H).





581
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.08 (s, 1H), 7.50-7.23 (m, 2H), 7.16-7.11 (m, 2H), 7.05-6.91 (m, 2H), 6.89- 6.77 (m, 2H), 5.48 (s, 1H).





582
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.28-8.12 (m, 2H), 7.83 (d, J = 1.5 Hz, 1H), 7.59- 7.51 (m, 2H), 7.55 (s, 1H), 7.34-7.26 (m, 2H), 7.09 (s, 1H), 5.72 (s, 1H).





583
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.33-8.27 (m, 2H), 7.70-7.62 (m, 2H), 7.60- 7.53 (m, 2H), 7.34-7.26 (m, 2H), 7.03 (s, 1H), 5.84 (s, 1H).





584
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.05-7.95 (m, 2H), 7.86-7.65 (m, 2H), 7.54- 7.44 (m, 2H), 7.35-7.23 (m, 1H), 7.09 (s, 1H), 5.76 (s, 1H).





585
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.14 (d, J = 1.5 Hz, 1H), 8.05 (dd, J = 7.5, 1.5 Hz, 1H), 7.79-7.73 (m, 2H), 7.54-7.44 (m, 2H), 7.35-7.28 (m, 1H), 7.04 (s, 1H), 5.89 (s, 1H).





586
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.52 (dd, J = 7.5, 1.5 Hz, 1H), 8.42 (dd, J = 7.0, 1.5 Hz, 1H), 7.96-7.81 (m, 2H), 7.60- 7.51 (m, 2H), 7.31-7.20 (m, 1H), 7.06 (s, 1H), 5.76 (s, 1H).





587
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.23 (s, 1H), 7.96-7.51 (m, 3H), 7.18 (d, J = 2.5 Hz, 1H), 7.08 (s, 1H), 6.68-6.51 (m, 1H), 5.75 (s, 1H).





588
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.06 (s, 1H), 7.90-7.80 (m, 2H), 7.58 (dd, J = 7.5, 1.5 Hz, 1H), 7.18 (d, J = 7.5 Hz, 1H), 7.02 (s, 1H), 6.56-6.47 (m, 1H), 5.82 (s, 1H).





589
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.06 (s, 1H), 7.90-7.80 (m, 2H), 7.58 (dd, J = 7.5, 1.5 Hz, 1H), 7.18 (d, J = 7.5 Hz, 1H), 7.02 (s, 1H), 6.56-6.45 (m, 1H), 5.82 (s, 1H).





590
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.77 (d, J = 1.5 Hz, 1H), 7.65 (d, J = 1.0 Hz, 1H), 7.14-7.05 (m, 3H), 6.62 (dd, J = 7.5, 1.5 Hz, 1H), 5.72 (s, 1H), 3.74 (s, 3H).





591
CF3


embedded image








592
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.02-7.93 (m, 2H), 7.65 (dd, J = 7.5, 1.5 Hz, 1H), 7.09 (s, 1H).





593
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.11-8.03 (m, 2H), 7.67 (dd, J = 7.5, 1.5 Hz, 1H), 7.17 (s, 1H), 7.09 (s, 1H), 5.68 (s, 1H), 2.50 (s, 3H).





594
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.86 (s, 1H), 8.57 (s, 1H), 7.99-7.81 (m, 2H), 7.48-7.36 (m, 2H), 7.29 (s, 1H).






595
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.83 (d, J = 1.5 Hz, 1H), 7.66-7.58 (m, 3H), 7.08 (s, 1H), 6.76 (dd, J = 7.5, 1.5 Hz, 1H), 5.63 (s, 1H).





596
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.33 (s, 1H), 8.31 (d, J = 1.5 Hz, 1H), 8.16 (d, J = 7.5 Hz, 1H), 7.81 (dd, J = 7.5, 1.5 Hz, 1H), 7.08 (s, 1H), 5.81 (s, 1H).





597
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.85 (d, J = 1.5 Hz, 1H), 7.79 (d, J = 7.5 Hz, 1H), 7.67 (dd, J = 7.5, 1.5 Hz, 1H), 7.03 (s, 1H), 5.84 (s, 1H), 2.61 (s, 3H).





598
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.25 (s, 1H), 7.99 (d, J = 1.5 Hz, 1H), 7.71 (d, J = 7.5 Hz, 1H), 7.59 (dd, J = 7.5, 1.5 Hz, 1H), 7.07 (s, 1H), 5.84 (s, 1H).





599
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.66 (d, J = 1.5 Hz, 1H), 7.58 (d, J = 7.5 Hz, 1H), 7.46 (dd, J = 7.5, 1.5 Hz, 1H), 7.06 (s, 6.75-6.69 (m, 1H), 6.45-6.33 (m, 1H), 5.60 (s, 1H), 3.22-3.12 (m, 2H).





600
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.18 (s, 1H), 8.09-8.00 (m, 1H), 7.31-7.25 (m, 2H), 7.21-7.15 (m, 2H), 5.98 (s, 1H).





601
CF3


embedded image








602
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.36 (d, J = 1.5 Hz, 1H), 8.06 (d, J = 7.5 Hz, 1H), 7.73 (dd, J = 7.5, 1.5 Hz, 1H), 7.15 (s, 1H), 5.93 (s, 1H).





603
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.22 (d, J = 1.5 Hz, 1H), 8.05 (d, J = 7.5 Hz, 1H), 7.66 (dd, J = 7.5, 1.5 Hz, 1H), 7.42 (d, J = 2.5 Hz, 1H), 7.32 (dd, J = 2.5, 1.6 Hz, 1H), 7.08 (s, 1H), 5.67 (s, 1H).





604
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.76 (d, J = 1.5 Hz, 1H), 7.69 (d, J = 7.5 Hz, 1H), 7.58 (dd, J = 7.5, 1.5 Hz, 1H), 7.08 (s, 1H), 6.28 (s, 1H), 5.71 (s, 1H), 2.86 (q, J = 8.0 Hz, 2H), 1.32 (t, J = 8.0 Hz, 3H).





605
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.34 (s, 1H), 8.38 (d, J = 1.5 Hz, 1H), 7.86 (d, J = 7.5 Hz, 1H), 7.78 (dd, J = 7.5, 1.5 Hz, 1H), 7.08 (s, 1H), 5.64 (s, 1H).





606
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.30 (s, 1H), 7.79-7.70 (m, 2H), 7.49 (dd, J = 7.5, 1.5 Hz, 1H), 7.02 (s, 1H), 5.82 (s, 1H).





607
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.41 (s, 1H), 7.95 (d, J = 1.5 Hz, 1H), 7.79 (d, J = 7.5 Hz, 1H), 7.60 (dd, J = 7.5, 1.5 Hz, 1H), 7.08 (s, 1H), 5.64 (s, 1H), 4.55 (q, J = 8.0 Hz, 2H), 1.63 (t, J = 8.0 Hz, 3H).





608
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.23 (d, J = 7.5 Hz, 1H), 7.15-7.07 (m, 2H), 6.59 (dd, J = 7.5, 1.5 Hz, 1H), 6.49 (d, J = 1.5 Hz, 1H), 5.87 (s, 1H), 3.10 (s, 2H), 2.90 (s, 6H).





609
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.82-7.74 (m, 2H), 7.73 (d, J = 1.5 Hz, 1H), 7.11 (d, J = 2.5 Hz, 1H), 7.02 (s, 1H), 6.50 (d, J = 2.5 Hz, 1H), 5.82 (s, 1H), 3.80 (s, 3H).





610
CF3


embedded image








611
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.30 (d, J = 1.5 Hz, 1H), 7.82-7.72 (m, 2H), 7.02 (s, 1H), 5.79 (s, 1H), 4.30 (s, 3H).





612
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.80-7.71 (m, 2H), 7.33-7.25 (m, 2H), 6.17 (s, 1H), 2.49 (s, 3H).





613
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.66-7.55 (m, 2H), 7.32-7.24 (m, 2H), 7.26- 7.18 (m, 2H), 6.04 (s, 1H).





614
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.18-8.08 (m, 2H), 7.58-7.50 (m, 2H), 7.29 (s, 1H).





615
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.72-7.58 (m, 3H), 7.29 (s, 1H).





616
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.66-7.52 (m, 2H), 7.30-7.20 (m, 2H), 7.09 (s, 1H).





617
CF3


embedded image








618
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.86 (s, 1H), 7.16 (d, J = 2.0 Hz, 1H), 7.08 (dd, J = 7.5, 2.0 Hz, 1H), 6.99 (d, J = 7.5 Hz, 1H), 5.34 (s, 1H), 4.32-4.25 (m, 4H).





619
CF3


embedded image








620
CF3


embedded image








621
CF3


embedded image








622
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.72 (d, J = 1.5 Hz, 1H), 9.43 (d, J = 7.5 Hz, 1H), 8.03 (dd, J = 7.5, 1.5 Hz, 1H), 7.24 (s, 1H), 5.86 (s, 1H).





623
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.50 (dd, J = 7.5, 1.5 Hz, 1H), 8.01 (dd, J = 7.0, 1.5 Hz, 1H), 7.82 (dd, J = 7.5, 7.0 Hz, 1H), 7.23 (s, 1H), 5.77 (s, 1H).





624
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.50 (s, 1H), 9.42 (s, 1H), 7.28 (s, 1H), 5.44 (s, 1H), 2.38 (s, 3H).





625
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.26 (s, 1H), 8.82 (d, J = 5.5 Hz, 1H), 8.75 (d, J = 5.5 Hz, 1H), 7.26 (s, 1H), 5.59 (s, 1H).





626
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.19 (s, 1H), 8.88 (s, 1H), 7.28 (s, 1H).





627
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.82-8.66 (m, 2H), 7.31 (s, 1H), 6.92-6.81 (m, 1H), 5.93-5.84 (m, 2H).





628
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.45 (s, 2H), 7.29 (s, 1H), 5.39 (s, 1H).





629
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.46 (s, 1H), 7.25 (s, 1H), 5.85 (s, 1H), 3.93 (s, 3H).





630
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.05 (s, 1H), 5.87 (s, 1H), 2.82 (s, 6H).





631
CF3


embedded image








632
CF3


embedded image








633
CF3


embedded image








634
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.25 (d, J = 1.5 Hz, 1H), 8.53 (d, J = 7.5 Hz, 1H), 8.11-8.04 (m, 2H), 7.91-7.82 (m, 3H), 5.50 (s, 1H).





635
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.13 (s, 1H), 8.64-8.51 (m, 2H), 8.39 (d, J = 7.5 Hz, 1H), 8.05-7.96 (m, 2H), 6.86 (s, 1H).





636
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.08 (d, J = 1.5 Hz, 1H), 8.61 (d, J = 7.5 Hz, 1H), 8.06 (dd, J = 7.5, 1.5 Hz, 1H), 7.91- 7.83 (m, 2H), 7.78-7.69 (m, 2H), 5.36 (s, 1H).





637
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.34 (d, J = 1.4 Hz, 1H), 8.78 (s, 1H), 8.10 (s, 1H), 8.00 (dt, J = 7.5, 1.6 Hz, 1H), 7.81 (dd, J = 7.3, 1.6 Hz, 1H), 7.65-7.53 (m, 2H), 5.49 (s, 1H).





638
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.00 (d, J = 7.5 Hz, 1H), 8.78 (d, J = 7.5 Hz, 1H), 8.37 (d, J = 1.5 Hz, 1H), 8.12 (d, J = 1.5 Hz, 1H), 7.86 (s, 1H), 5.16 (s, 1H).





639
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.78-8.60 (m, 2H), 8.40 (d, J = 1.5 Hz, 1H), 8.27 (d, J = 7.5 Hz, 1H), 7.94 (dd, J = 7.5, 1.5 Hz, 1H), 7.89 (s, 1H), 5.46 (s, 1H).





640
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.68 (s, 1H), 8.25 (dd, J = 7.5, 1.5 Hz, 1H), 8.18- 8.11 (m, 3H), 7.74 (s, 1H).





641
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.92 (s, 1H), 8.40 (d, J = 1.5 Hz, 1H), 8.25 (d, J = 7.5 Hz, 1H), 7.92 (dd, J = 7.5, 1.5 Hz, 1H), 7.89 (s, 1H), 5.43 (s, 1H), 2.93 (q, J = 8.0 Hz, 2H), 1.27 (t, J = 8.0 Hz, 3H).





642
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.84 (s, 1H), 6.81 (dd, J = 7.5, 7.0 Hz, 1H), 6.66 (dd, J = 7.5, 2.0 Hz, 1H), 6.44 (dd, J = 7.0, 2.0 Hz, 1H), 5.20 (s, 1H), 4.24 (s, 1H), 3.04-2.89 (m, 4H), 2.15-2.07 (m, 2H).





643
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.85 (s, 1H), 7.14 (dd, J = 7.5, 2.0 Hz, 1H), 6.83 (d, J = 2.0 Hz, 1H), 6.67 (d, J = 7.5 Hz, 1H), 5.34 (s, 1H), 3.33-3.17 (m, 2H), 2.95-2.87 (m, 5H), 2.10-2.02 (m, 2H).





644
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.83 (s, 1H), 6.55-6.44 (m, 3H), 5.87 (s, 1H), 3.95 (s, 1H), 3.72-3.58 (m, 2H), 3.41- 3.25 (m, 2H), 2.99-2.87 (m, 1H), 1.88- 1.79 (m, 1H), 1.19-1.09 (m, 2H), 0.91-0.82 (m, 2H).





645
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.23-7.16 (m, 2H), 7.08-6.88 (m, 2H), 6.77 (s, 1H), 5.87 (s, 1H), 3.52-3.39 (m, 2H), 2.90-2.77 (m, 2H), 2.11-2.03 (m, 2H).





646
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.95-9.86 (m, 2H), 8.29 (dd, J = 2.5, 1.5 Hz, 1H), 8.15 (dd, J = 7.5, 1.5 Hz, 1H), 8.10 (d, J = 7.5 Hz, 1H), 7.86 (s, 1H), 5.70 (s, 1H).





647
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.95 (d, J = 1.5 Hz, 1H), 9.69 (s, 1H), 8.08-7.99 (m, 2H), 7.94 (d, J = 7.5 Hz, 1H), 7.89 (s, 1H), 5.46 (s, 1H).





648
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.10 (s, 1H), 8.05 (dd, J = 7.5, 1.5 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 6.74 (d, J = 1.5 Hz, 1H), 5.35 (s, 1H), 3.87 (s, 3H).





649
CF3


embedded image








650
CF3


embedded image








651
CF3


embedded image








652
CF3


embedded image








653
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.31 (d, J = 5.5 Hz, 1H), 8.28 (dd, J = 7.5, 1.5 Hz, 1H), 8.00 (d, J = 7.5 Hz, 1H), 7.90 (s, 1H), 7.87-7.76 (m, 2H), 5.50 (s, 1H).





654
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.33 (d, J = 7.5 Hz, 1H), 8.41 (d, J = 7.5 Hz, 1H), 8.10 (dd, J = 7.5, 1.5 Hz, 1H), 8.02 (d, J = 1.5 Hz, 1H), 7.94 (d, J = 7.5 Hz, 1H), 7.90 (s, 1H), 5.59 (s, 1H).





655
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.39 (d, J = 7.5 Hz, 1H), 9.01 (d, J = 1.5 Hz, 1H), 8.85 (s, 1H), 8.75 (d, J = 1.5 Hz, 1H), 8.62 (d, J = 7.5 Hz, 1H), 6.80 (s, 1H), 3.17 (s, 3H).





656
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.39 (s, 1H), 8.01-7.85 (m, 2H), 8.75-8.62 (m, 2H), 6.80 (s, 1H).





657
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.11 (s, 2H), 7.24 (s, 1H), 5.84 (s, 1H).





658
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.77 (s, 1H), 9.32 (s, 1H), 7.30 (s, 1H), 5.30 (s, 1H).





659
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.00 (s, 2H), 7.25 (s, 1H), 5.76 (s, 1H).





660
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.19 (s, 1H), 7.37 (s, 1H), 7.08 (s, 2H), 5.32 (s, 1H), 2.82 (s, 3H).





661
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.05 (s, 1H), 7.26 (s, 1H), 5.59 (s, 1H), 2.84 (s, 3H).





662
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.25 (s, 1H), 5.68 (s, 1H).





663
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.25 (s, 2H), 8.30 (s, 1H), 7.34 (s, 1H), 4.98 (s, 1H), 2.11 (s, 3H).





664
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.83 (s, 1H), 9.34 (s, 1H), 7.49 (s, 1H), 6.57 (s, 1H), 3.96 (s, 3H).





665
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.57 (s, 2H), 7.25 (s, 1H), 5.91 (s, 1H).





666
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.21 (s, 2H), 7.24 (s, 1H), 5.84 (s, 1H), 3.83 (s, 3H).





667
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.23 (s, 1H), 9.05 (s, 1H), 7.34 (s, 1H), 3.99 (s, 3H), 3.83 (s, 3H).





668
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.60 (s, 1H), 9.15 (d, J = 5.0 Hz, 1H), 7.86 (d, J = 5.0 Hz, 1H), 7.27 (s, 1H).





669
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.60 (s, 1H), 7.71 (s, 1H), 7.27 (s, 1H), 2.27 (q, J = 8.0 Hz, 2H), 1.19 (t, J = 8.0 Hz, 3H).





670
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.86 (d, J = 5.0 Hz, 1H), 7.52 (d, J = 5.0 Hz, 1H), 7.28 (s, 1H), 4.29 (q, J = 8.0 Hz, 2H), 1.29 (t, J = 8.0 Hz, 3H).





671
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.87 (s, 1H), 8.82 (s, 1H), 7.35 (s, 1H), 3.00 (s, 3H), 2.68 (s, 3H).





672
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.73 (s, 1H), 7.27 (s, 1H), 2.60 (s, 3H), 2.45 (s, 3H).





673
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.06 (s, 1H), 7.27 (s, 1H), 2.35 (s, 3H).





674
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.27 (s, 1H), 3.19 (s, 3H), 2.49 (s, 3H), 2.39 (s, 3H).





675
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.96 (s, 1H), 8.63 (s, 1H), 7.28 (s, 1H).





676
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.30 (s, 1H), 8.59 (s, 1H), 7.20 (s, 1H), 2.49 (s, 3H).





677
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.02 (d, J = 5.0 Hz, 2H), 7.47 (t, J = 5.0 Hz, 1H), 7.26 (s, 1H).





678
CF3


embedded image








679
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.26 (s, 1H), 6.51 (s, 1H), 2.67 (s, 3H).





680
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.05 (s, 1H), 7.26 (s, 1H), 3.47 (hept, J = 8.0 Hz, 1H), 2.66 (s, 3H), 1.47 (d, J = 8.0 Hz, 1H).





681
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.22 (s, 1H), 5.71 (s, 1H), 2.70 (s, 6H), 2.34 (s, 3H).





682
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.72 (s, 2H), 7.25 (s, 1H), 6.80 (s, 1H), 5.87 (s, 1H).





683
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.72 (s, 2H), 7.25 (s, 1H), 1.70-1.56 (m, 1H), 1.06-0.97 (m, 2H), 0.78-0.69 (m, 2H).





684
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.17 (d, J = 5.0 Hz, 1H), 8.06 (d, J = 5.0 Hz, 1H), 7.27 (s, 1H), 2.73 (q, J = 8.0 Hz, 2H), 1.34 (t, J = 8.0 Hz, 3H).





685
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.88 (d, J = 5.0 Hz, 1H), 7.88 (d, J = 5.0 Hz, 1H), 7.26 (s, 1H), 5.62-5.52 (m, 2H), 1.73- 1.44 (m, 3H).





686
CF3


embedded image








687
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.24 (s, 1H), 7.25 (s, 1H), 5.64 (s, 1H), 4.48 (s, 2H), 3.40 (s, 3H).





688
CF3


embedded image








689
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.96 (d, J = 5.0 Hz, 1H), 7.36-7.28 (m, 2H), 7.21 (d, J = 5.0 Hz, 1H), 6.90 (s, 1H), 6.45 (d, J = 2.5 Hz, 1H), 5.61 (dd, J = 2.5, 1.5 Hz, 1H).





690
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.94 (s, 1H), 9.47 (s, 1H), 8.95 (s, 1H), 7.45 (s, 1H), 5.98 (s, 1H), 3.44 (s, 2H), 2.78 (s, 3H).





691
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.49 (s, 1H), 7.39 (s, 1H), 7.24 (s, 1H), 5.77 (s, 1H), 5.10 (s, 2H), 2.66 (hept, J = 7.0 Hz, 1H), 1.18 (d, J = 7.0 Hz, 6H).





692
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.38 (s, 1H), 9.05 (s, 1H), 8.40 (s, 1H), 7.49 (s, 1H), 4.48 (s, 2H), 3.34 (s, 3H).





693
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.60 (d, J = 1.5 Hz, 1H), 7.71 (s, 1H), 7.24 (s, 1H), 5.72 (s, 1H), 3.62 (s, 2H), 2.68 (s, 6H).





694
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.19 (s, 2H), 7.29 (s, 1H), 5.40 (s, 1H), 4.66 (s, 2H), 3.60 (q, J = 8.0 Hz, 2H), 1.15 (t, J = 8.0 Hz, 3H).





695
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.12 (s, 1H), 9.05 (s, 1H), 7.26 (s, 1H), 6.48- 6.33 (m, 1H), 6.21 (s, 1H), 5.91-5.78 (m, 2H).





696
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.90 (d, J = 5.0 Hz, 1H), 8.11 (dd, J = 2.5, 2.0 Hz, 1H), 8.06-7.96 (m, 2H), 7.92 (t, J = 2.0 Hz, 1H), 7.28 (s, 1H).





697
CF3


embedded image








698
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.89 (d, J = 5.0 Hz, 1H), 7.59 (d, J = 5.0 Hz, 1H), 7.24 (s, 1H), 5.83 (s, 1H), 4.53 (s, 2H), 4.09 (s, 2H), 3.43 (s, 3H).





699
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.16 (s, 1H), 8.95 (s, 1H), 7.27 (s, 1H), 6.78 (s, 1H), 4.02-3.94 (m, 2H), 1.84-1.71 (m, 1H), 1.49-1.38 (m, 1H), 1.18- 1.00 (d, J = 6.8 Hz, 3H), 0.97-0.82 (m, 4H).





700
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.48 (s, 1H), 7.34 (s, 1H), 7.21 (s, 1H), 4.33 (t, J = 7.5 Hz, 2H), 3.64 (s, 3H), 2.67 (t, J = 7.5 Hz, 2H).





701
CF3


embedded image








702
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.77 (s, 1H), 7.25 (s, 1H), 5.89 (s, 1H), 3.72 (q, J = 8.0 Hz, 2H), 3.44 (s, 2H), 3.08 (s, 3H), 1.23 (t, J = 8.0 Hz, 3H).





703
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.98 (d, J = 5.0 Hz, 1H), 7.24-7.19 (m, 2H), 4.32 (s, 2H).





704
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.97 (s, 1H), 7.88 (s, 1H), 7.83 (s, 1H), 7.29 (s, 1H), 3.89 (s, 3H).





705
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.96 (s, 2H), 7.26 (s, 1H), 4.67 (s, 2H), 4.37 (s, 2H) 2.41 (s, 3H).





706
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.34 (s, 1H), 7.79 (s, 1H), 7.26 (s, 1H), 4.53 (s, 2H), 4.09 (s, 2H), 3.34 (s, 3H).





707
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.09 (s, 1H), 8.70 (d, J = 5.0 Hz, 2H), 7.64 (d, J = 5.0 Hz, 2H), 7.28 (s, 1H), 7.18 (s, 1H), 3.67 (q, J = 8.0 Hz, 2H), 1.34 (t, J = 8.0 Hz, 3H).





708
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.24 (s, 2H), 7.35 (s, 1H), 5.71 (s, 2H), 3.63 (s, 2H), 3.43 (s, 3H).





709
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.26 (d, J = 1.5 Hz, 1H), 8.43 (t, J = 1.5 Hz, 1H), 8.27-8.18 (m, 2H), 8.10 (s, 1H), 7.62- 7.48 (m, 2H), 5.74 (s, 1H), 2.10 (s, 3H).





710
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.06 (dd, J = 7.5, 1.5 Hz, 1H), 7.53-7.41 (m, 1H), 7.30-7.23 (m, 2H), 7.06 (s, 1H), 6.97 (d, J = 1.5 Hz, 1H), 6.02 (s, 2H), 5.53 (s, 1H), 3.30 (s, 3H).





711
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.17-8.14 (m, 2H), 7.78-7.68 (m, 3H), 7.55- 7.39 (m, 1H), 5.41 (s, 1H), 4.78 (s, 2H), 3.40 (s, 3H).





712
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.58 (d, J = 1.5 Hz, 1H), 8.34 (d, J = 7.5 Hz, 1H), 8.10 (dd, J = 7.5, 1.5 Hz, 1H), 7.56 (s, 1H), 7.04 (s, 1H), 5.72 (s, 1H).





713
CF3


embedded image








714
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.90 (dd, J = 7.5, 1.5 Hz, 1H), 8.36 (d, J = 7.5 Hz, 1H), 8.25-8.16 (m, 3H), 7.39-7.26 (m, 1H), 7.03 (s, 1H), 5.72 (s, 1H).





715
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.14 (d, J = 7.5 Hz, 1H), 8.17-8.14 (m, 2H), 7.76- 7.68 (m, 3H), 7.57-7.41 (m, 1H), 5.48 (s, 1H).





716
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.81 (dd, J = 7.5, 1.5 Hz, 1H), 8.19-8.10 (m, 2H), 7.93 (d, J = 1.5 Hz, 1H), 7.87 (s, 1H), 7.51 (dd, J = 7.5, 5.0 Hz, 1H), 5.47 (s, 1H), 5.30 (d, J = 73.5 Hz, 1H).





717
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.15 (dd, J = 7.5, 1.7 Hz, 1H), 8.88 (d, J = 1.5 Hz, 1H), 8.45-8.37 (m, 2H), 7.58 (dd, J = 7.5, 5.5 Hz, 1H), 6.99 (s, 1H).





718
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.84 (d, J = 7.5 Hz, 1H), 7.97-7.88 (m, 2H), 7.73 (dd, J = 7.5, 1.5 Hz, 1H), 7.51 (dd, J = 7.5, 7.0 Hz, 1H), 6.94 (dd, J = 7.5, 1.5 Hz, 1H), 5.70 (s, 1H), 3.29 (q, J = 8.0 Hz, 2H), 2.98 (s, 3H), 1.20 (t, J = 8.0 Hz, 3H).





719
CF3


embedded image








720
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.33 (d, J = 1.5 Hz, 1H), 8.50 (dd, J = 2.5, 1.5 Hz, 1H), 8.19 (d, J = 1.5 Hz, 1H), 8.04- 7.90 (m, 2H), 5.08 (s, 1H), 3.27 (s, 3H).





721
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.89 (d, J = 5.5 Hz, 1H), 8.15 (s, 1H), 7.87 (d, J = 1.5 Hz, 1H), 7.77 (d, J = 1.5 Hz, 1H), 7.12 (s, 1H), 6.85 (d, J = 5.5 Hz, 1H), 5.27-5.14 (m, 2H), 2.64 (s, 3H), 2.46 (s, 3H).





722
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.29 (d, J = 1.5 Hz, 1H), 8.99 (s, 1H), 8.74 (q, J = 1.5 Hz, 1H), 7.86-7.79 (m, 2H), 6.82 (s, 1H), 2.49 (s, 3H), 2.44 (s, 3H).





723
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.90 (d, J = 6.5 Hz, 1H), 8.35 (d, J = 1.5 Hz, 1H), 8.14 (dd, J = 6.5, 1.5 Hz, 1H), 7.94 (dd, J = 7.5, 1.5 Hz, 1H), 7.84 (dd, J = 7.5, 1.5 Hz, 1H), 7.38 (d, J = 7.5 Hz, 1H), 6.85 (s, 1H).





724
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.29 (d, J = 1.5 Hz, 1H), 8.38 (dd, J = 2.0, 1.5 Hz, 1H), 8.15 (dd, J = 7.5, 1.5 Hz, 1H), 8.13 (s, 1H), 7.88-7.70 (m, 2H), 7.54-7.41 (m, 1H), 5.43 (s, 1H).





725
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.92 (d, J = 5.5 Hz, 1H), 8.52 (d, J = 1.5 Hz, 1H), 8.35 (d, J = 5.5 Hz, 1H), 8.08 (dd, J = 7.5, 1.5 Hz, 1H), 7.50 (d, J = 7.5 Hz, 1H), 7.09 (s, 1H), 5.46 (s, 1H).





726
CF3


embedded image








727
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.42 (d, J = 1.5 Hz, 1H), 8.72 (d, J = 1.5 Hz, 1H), 8.37 (dd, J = 7.5, 1.5 Hz, 1H), 8.04 (dd, J = 7.5, 7.0 Hz, 1H), 7.94 (dd, J = 7.0, 1.5 Hz, 1H), 7.90 (s, 1H), 5.37 (s, 1H).





728
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.00 (s, 1H), 8.16-8.09 (m, 2H), 7.93 (d, J = 7.5 Hz, 1H), 7.66 (dd, J = 7.5, 7.0 Hz, 1H), 6.96 (s, 1H), 2.73-2.56 (m, 1H), 2.29-2.14 (m, 1H), 2.18-2.01 (m, 3H), 1.98-1.84 (m, 2H), 1.62-1.45 (m, 3H).





729
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.70 (d, J = 7.5 Hz, 1H), 8.44 (d, J = 1.5 Hz, 1H), 8.38 (s, 1H), 8.04 (s, 1H), 7.63 (dd, J = 7.5, 1.5 Hz, 1H), 3.95 (s, 3H).





730
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.70 (d, J = 1.5 Hz, 1H), 8.44-8.38 (m, 2H), 8.04 (s, 1H), 7.63 (dd, J = 7.5, 1.7 Hz, 1H), 3.95 (s, 3H).





731
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.52 (d, J = 7.5 Hz, 1H), 8.44 (dd, J = 7.5, 1.5 Hz, 1H), 8.14-8.08 (m, 2H), 8.03 (s, 1H), 7.69 (dd, J = 7.5, 1.5 Hz, 1H), 3.03 (s, 3H), 2.85 (s, 3H).





732
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.54-7.31 (m, 1H), 7.04-6.94 (m, 2H), 6.92- 6.71 (m, 1H), 5.50 (s, 1H).





733
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 8.39- 8.31 (m, 1H), 8.21-8.18 (m, 1H), 7.55- 7.52 (m, 1H), 7.35 (s, 1H).






734
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.10 (dd, J = 7.5, 1.5 Hz, 1H), 8.29-8.16 (m, 2H), 7.99-7.72 (m, 2H), 7.52-7.39 (m, 1H), 7.17 (s, 1H).





735
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.35 (dd, J = 7.5, 7.0 Hz, 1H), 7.16 (dd, J = 7.5, 1.5 Hz, 1H), 7.09 (dd, J = 7.0, 1.5 Hz, 1H), 7.04 (s, 1H), 5.76 (s, 1H), 2.31 (s, 3H), 1.95-1.85 (m, 1H), 1.07-0.98 (m, 2H), 0.89-0.80 (m, 2H).





736
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.52 (dd, J = 11.0, 2.0 Hz, 1H), 7.44-7.21 (m, 1H), 7.30-7.25 (m, 2H), 7.07 (s, 1H), 5.50 (s, 1H).





737
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.61-7.52 (m, 2H), 7.48-7.40 (m, 2H), 7.04 (s, 1H), 5.69 (s, 1H).





738
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.68-7.61 (m, 2H), 7.00 (s, 1H), 6.75-6.68 (m, 2H), 5.76 (s, 1H), 4.56 (s, 2H).





739
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.47-7.37 (m, 4H), 7.07 (s, 1H), 5.48 (s, 1H).





740
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.62 (dd, J = 5.5, 2.0 Hz, 1H), 7.36-7.25 (m, 1H), 7.16 (dd, J = 11.0, 7.5 Hz, 1H), 7.01 (s, 1H), 5.81 (s, 1H).





741
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.30-7.23 (m, 2H), 7.10 (s, 1H), 5.62 (s, 1H), 3.89 (s, 3H).





742
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.94-7.74 (m, 2H), 7.67-7.55 (m, 2H), 7.07 (s, 1H), 5.49 (s, 1H).





743
CF3


embedded image


(500 MHz, Chloroform-d) δ 9.38 (d, J = 1.5 Hz, 1H), 8.16 (d, J = 1.5 Hz, 1H), 7.98-7.92 (m, 2H), 7.64-7.51 (m, 2H), 7.15 (s, 1H).





744
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.45-7.25 (m, 2H), 7.18-7.05 (m, 1H), 7.01 (s, 1H), 5.81 (s, 1H).





745
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.50 (dd, J = 7.5, 5.5 Hz, 1H), 7.45 (dd, J = 11.0, 2.0 Hz, 1H), 7.24-7.11 (m, 1H), 7.01 (s, 1H), 5.80 (s, 1H).





746
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.73 (d, J = 7.5 Hz, 2H), 7.54 (d, J = 7.5 Hz, 2H), 7.07 (s, 1H), 5.48 (s, 1H).





747
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.37-7.33 (m, 1H), 7.25 (dd, J = 7.5, 1.5 Hz, 1H), 7.14 (d, J = 7.5 Hz, 1H), 7.06 (s, 1H), 5.57 (s, 1H), 2.30 (s, 3H), 2.20 (s, 3H).





748
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.32 (d, J = 1.5 Hz, 1H), 7.26-7.17 (m, 2H), 7.03 (s, 1H), 5.67 (s, 1H), 2.50 (s, 3H), 2.35 (s, 3H).





749
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.53 (d, J = 7.5 Hz, 2H), 7.42 (d, J = 7.5 Hz, 2H), 7.06 (s, 1H), 5.49 (s, 1H), 2.45 (s, 3H).





750
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.57 (dd, J = 2.0, 1.5 Hz, 1H), 8.27-8.16 (m, 1H), 7.95-7.71 (m, 2H), 7.03 (s, 1H), 5.85 (s, 1H).





751
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.76 (dd, J = 2.0, 1.5 Hz, 1H), 7.61-7.52 (m, 1H), 7.50-7.41 (m, 2H), 7.01 (s, 1H), 5.78 (s, 1H).





752
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.56-7.47 (m, 3H), 7.42-7.30 (m, 1H), 7.00 (s, 1H), 5.61 (s, 1H).





753
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.35 (d, J = 7.5 Hz, 1H), 7.20 (d, J = 7.5 Hz, 1H), 7.03 (s, 1H), 5.66 (s, 1H).





754
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.47 (d, J = 7.5 Hz, 2H), 7.09-7.03 (m, 3H), 5.49 (s, 1H), 4.00 (t, J = 7.5 Hz, 2H), 1.74- 1.50 (m, 4H), 1.04 (t, J = 8.0 Hz, 3H).





755
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.09 (d, J = 2.0 Hz, 1H), 7.92 (dd, J = 7.5, 2.0 Hz, 1H), 7.83 (d, J = 7.5 Hz, 1H), 7.05 (s, 1H), 5.49 (s, 1H).





756
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.13 (d, J = 1.5 Hz, 1H), 7.78-7.70 (m, 2H), 7.05 (s, 1H), 5.54 (s, 1H).





757
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.80 (d, J = 2.0 Hz, 1H), 8.62 (dd, J = 7.5, 2.0 Hz, 1H), 8.11 (d, J = 7.5 Hz, 1H), 7.01 (s, 1H), 5.69 (s, 1H).





758
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.06 (d, J = 2.0 Hz, 1H), 7.75 (dd, J = 7.5, 2.0 Hz, 1H), 7.17 (d, J = 7.5 Hz, 1H), 7.08 (s, 1H), 5.29 (s, 1H), 4.02 (s, 3H).





759
CF3


embedded image


(500 MHz, Chloroform-d) δ 8.48 (s, 2H), 7.02 (s, 1H), 5.86 (s, 1H), 3.97 (s, 3H).





760
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.87 (d, J = 1.5 Hz, 1H), 7.56-7.50 (m, 2H), 6.99 (s, 1H), 5.62 (s, 1H), 2.48 (s, 3H).





761
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.70-7.63 (m, 2H), 7.20-7.07 (m, 2H), 5.43 (s, 1H).





762
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.75 (s, 1H), 9.34 (d, J = 2.0 Hz, 1H), 8.69 (dd, J = 8.0, 2.0 Hz, 1H), 8.09 (d, J = 8.0 Hz, 1H), 7.38 (s, 1H).






763
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.77 (d, J = 2.0 Hz, 1H), 7.49 (d, J = 7.5 Hz, 1H), 7.43 (dd, J = 7.5, 2.0 Hz, 1H), 7.04 (s, 1H), 5.65 (s, 1H).





764
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.43-7.36 (m, 1H), 7.35-7.23 (m, 2H), 7.01 (s, 1H), 5.69 (s, 1H).





765
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.33-7.22 (m, 3H), 7.01 (s, 1H), 6.85-6.69 (m, 1H), 5.79 (s, 1H), 3.87 (s, 3H).





766
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.37-7.23 (m, 1H), 7.22-7.11 (m, 2H), 7.12 (s, 1H), 5.50 (s, 1H).





767
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.44 (s, 1H), 8.78 (s, 1H), 8.47-8.35 (m, 1H), 7.99-7.87 (m, 1H), 7.30 (s, 1H), 3.88 (s, 3H).






768
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.27 (s, 1H), 8.99 (d, J = 2.0 Hz, 1H), 8.42 (dd, J = 8.5, 2.0 Hz, 1H), 7.61 (d, J = 8.5 Hz, 1H), 7.25 (s, 1H).






769
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.80 (d, J = 2.5 Hz, 1H), 7.61 (dd, J = 7.5, 2.5 Hz, 1H), 7.53 (d, J = 7.5 Hz, 1H), 7.01 (s, 1H), 5.66 (s, 1H).





770
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 9.07 (d, J = 2.0 Hz, 1H), 8.67 (d, J = 2.5 Hz, 1H), 8.41 (dd, J = 2.5, 2.0 Hz, 1H), 7.24 (s, 1H).






771
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.30 (d, J = 2.0 Hz, 1H), 7.22 (dd, J = 7.5, 2.0 Hz, 1H), 7.06-6.98 (m, 2H), 6.07 (s, 2H), 5.78 (s, 1H).





772
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.65 (dd, J = 7.5, 2.0 Hz, 1H), 7.46-7.29 (m, 3H), 7.05 (s, 1H), 5.66 (s, 1H).





773
CF3


embedded image








774
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.27 (br, 1H), 5 7.61 (d, J = 1.5 Hz, 1H), 7.38 (s, 1H), 6.99 (d, J = 1.5 Hz, 1H), 4.09 (s, 3H).






775
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.38 (s, 1H), 7.07 (s, 1H), 6.70 (s, 1H), 3.86 (s, 3H).






776
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.19 (s, 1H), 7.15 (s, 1H), 6.87 (s, 1H), 3.90 (s, 3H).






777
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.40 (s, 1H), 7.34 (s, 1H), 6.97 (s, 1H), 3.87 (s, 3H).






778
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.38 (s, 1H), 7.37 (s, 1H), 6.80 (s, 1H), 3.76 (s, 3H).






779
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.27 (br, 1H), 5 7.32 (s, 1H), 6.68 (s, 1H), 3.91 (s, 3H), 2.19 (s, 3H).






780
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.64 (s, 1H), 6.90 (s, 1H), 6.60 (s, 1H), 3.88 (s, 3H), 2.60 (q, J = 8.0 Hz, 2H), 1.19 (t, J = 8.0 Hz, 3H).






781
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.48 (s, 1H), 6.93 (s, 1H), 6.37 (s, 1H), 3.76 (s, 3H), 1.87-1.73 (m, 1H), 1.20-0.91 (m, 2H), 0.75-0.68 (m, 2H).






782
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.25 (s, 1H), 6.85 (s, 1H), 5.96 (s, 1H), 3.92 (s, 3H), 3.84 (s, 3H).






783
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.26 (s, 1H), 6.90 (s, 1H), 5.86 (s, 1H), 4.39 (q, J = 8.0 Hz, 2H), 3.89 (s, 3H), 1.36 (t, J = 8.0 Hz, 3H).






784
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.64 (s, 1H), 7.47-7.39 (m, 2H), 7.18-7.11 (m, 2H), 7.03-6.94 (m, 2H), 6.06 (s, 1H), 4.65 (s, 2 H), 3.83 (s, 3H).






785
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.23 (s, 1H), 7.21 (s, 1H), 6.86 (s, 1H), 3.88 (s, 3H), 3.55 (br, 2 H).






786
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.66 (s, 1H), 8.17 (s, 1H), 6.95 (s, 1H), 6.26 (s, 1H), 3.91 (s, 3H), 3.03 (s, 3H).






787
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.45 (s, 1H), 6.85 (s, 1H), 6.36 (s, 1H), 3.94 (s, 3H), 3.19 (s, 6H).






788
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.52 (s, 1H), 7.38 (s, 1H), 6.94 (s, 1H), 5.56 (s, 1H), 3.88 (s, 3H), 2.13 (s, 3H).






789
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.06 (s, 1H), 8.56 (s, 1H), 7.85 (s, 1H), 6.95 (s, 1H), 5.56 (s, 1H), 3.90 (s, 3H), 2.71 (s, 3H).






790
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ13.18 (s, 1H), 10.14 (s, 1H), 6.94 (s, 1H), 5.56 (s, 1H), 3.95 (s, 3H), 1.29 (s, 9H).






791
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.72 (s, 1H), 6.99 (s, 1H), 6.92 (s, 1H), 3.91 (s, 3H).






792
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.58 (s, 1H), 7.50 (s, 1H), 6.91 (s, 1H), 3.87 (s, 3H).






793
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.25 (s, 1H), 7.92-7.85 (m, 2H), 7.51-7.41 (m, 3H), 7.25 (s, 1H), 6.99 (s, 1H), 3.92 (s, 3H).






794
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.25 (s, 1H), 6.94 (t, J = 73.5 Hz, 1 H), 6.90 (s, 1H), 6.84 (s, 1H), 3.89 (s, 3H).






795
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ13.51 (s, 1H), 6.91 (s, 1H), 6.71 (s, 1H), 3.89 (s, 3H), 3.07 (s, 2H).






796
CF3


embedded image








797
CF3


embedded image








798
CF3


embedded image








799
CF3


embedded image








800
CF3


embedded image








801
CF3


embedded image








802
CF3


embedded image








803
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.78 (s, 1H), 7.37 (s, 1H), 3.76 (s, 3H), 2.70 (s, 3H).






804
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.48 (s, 1H), 7.50 (s, 1H), 6.37 (s, 1H), 3.76 (s, 3H).






805
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.59 (s, 1H), 7.87 (s, 1H), 6.89 (s, 1H), 3.88 (s, 3H).






806
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.42 (s, 1H), 8.12 (s, 1H), 6.90 (s, 1H), 3.86 (s, 3H).






807
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.38 (s, 1H), 7.60 (s, 1H), 6.37 (s, 1H), 3.76 (s, 3H).






808
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.40 (s, 1H), 7.56 (s, 1H), 6.88 (s, 1H), 3.85 (s, 3H), 2.08 (s, 3H).






809
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.38 (s, 1H), 7.67 (s, 1H), 6.89 (s, 1H), 3.84 (s, 3H), 2.70 (q, J = 8.0 Hz, 2H), 1.17 (t, J = 8.0 Hz, 3H).






810
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.68 (s, 1H), 7.76 (s, 1H), 6.37 (s, 1H), 3.76 (s, 3H), 2.41-2.28 (m, 1H), 1.12-1.02 (m, 2H), 0.82-0.72 (m, 2H).






811
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.78 (s, 1H), 7.19 (s, 1H), 6.90 (s, 1H), 3.90 (s, 3H), 3.80 (s, 3H).






812
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.87 (s, 1H), 7.19 (s, 1H), 6.90 (s, 1H), 4.10 (q, J = 8.0 Hz, 2H), 3.90 (s, 3H), 1.34 (t, J = 8.0 Hz, 3H).






813
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.78 (s, 1H), 7.50-7.44 (m, 2H), 7.41-7.27 (m, 4H), 6.95 (s, 1H), 5.15 (s, 2H), 3.91 (s, 3H).






814
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.03 (s, 1H), 7.70 (s, 1H), 6.86 (s, 1H), 5.83 (s, 2H), 3.89 (s, 3H).






815
CF3


embedded image








816
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.35 (s, 1H), 7.71 (s, 1H), 6.90 (s, 1H), 3.89 (s, 3H), 2.86 (s, 6H).






817
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.03 (s, 1 H) 9.96 (s, 1H), 7.87 (s, 1H), 6.95 (s, 1H), 3.92 (s, 3H), 2.07 (s, 3H).






818
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.66 (s, 1H), 8.60 (s, 1H), 7.87 (s, 1H), 6.97 (s, 1H), 6.16 (s, 1H), 3.93 (s, 3H), 2.68 (s, 3H).






819
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.35 (s, 1H), 9.78 (s, 1H), 7.87 (s, 1H), 6.95 (s, 1H), 3.92 (s, 3H), 1.49 (s, 9H).






820
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.21 (s, 1H), 7.92 (s, 1H), 6.92 (s, 1H), 3.87 (s, 3H).






821
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.45 (s, 1H), 8.27 (s, 1H), 6.89 (s, 1H), 3.89 (s, 3H).






822
CF3


embedded image








823
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.10 (s, 1H), 7.82 (s, 1H), 6.92 (s, 1H), 3.85 (s, 3H).






824
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.36 (s, 1H), 7.91 (s, 1H), 6.95 (s, 1H), 6.67 (t, J = 73.5 Hz, 1H), 3.83 (s, 3H).






825
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.16 (s, 1H), 7.77 (s, 1H), 6.93 (s, 1H), 3.83 (s, 3H), 3.07 (s, 2H).






826
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.89 (s, 1H), 7.61 (d, J = 2.5 Hz, 1H), 7.15 (s, 1H), 6.84 (d, J = 2.5 Hz, 1H), 3.68 (q, J = 8.0 Hz, 2H), 1.53 (t, J = 8.0 Hz, 3H).






827
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.78 (s, 1H), 7.16 (s, 1H), 6.37 (s, 1H), 4.08 (q, J = 8.0 Hz, 2H), 1.87-1.76 (m, 1H), 1.30 (t, J = 8.0 Hz, 3H), 1.12-0.88 (m, 2H), 0.71-0.63 (m, 2H).






828
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.57 (s, 1H), 7.60 (d, J = 2.0 Hz, 1H), 7.03 (s, 1H), 6.73 (d, J = 2.0 Hz, 1H), 4.15-3.82 (m, 1H), 1.26 (d, J = 6.5 Hz, 6H).






829
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.76 (s, 1H), 7.06 (s, 1H), 6.78 (s, 1H), 4.56- 4.23 (m, 1H), 2.39 (s, 3H), 1.26 (d, J = 4.5 Hz, 6H).






830
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.08 (s, 1H), 7.17 (d, J = 8.5 Hz, 1H), 6.50 (s, 1H), 4.46-4.09 (m, 1H), 1.40 (d, J = 4.5 Hz, 6H).






831
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ13.51 (s, 1H), 7.64 (d, J = 2.5 Hz, 1H), 6.91 (s, 1H), 6.68 (d, J = 2.5 Hz, 1H), 5.32 (s, 2H).






832
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ13.11 (s, 1H), 7.96 (d, J = 2.5 Hz, 1H), 7.65- 7.51 (m, 2H), 7.46-7.24 (m, 2H), 7.12- 7.01 (m, 2H), 6.83 (s, 1H).






833
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.63 (s, 1H), 7.64 (d, J = 2.0 Hz, 1H), 7.55- 7.15 (m, 2H), 7.32-7.24 (m, 1H), 7.22- 7.16 (m, 2H), 6.90 (s, 1H), 6.62 (d, J = 2.0 Hz, 1H), 5.46 (s, 2H).






834
CF3


embedded image



1H NMR (500 MHz, Chloroform-d) δ 7.84 (d, J = 2.5 Hz, 1H), 7.21 (s, 1H), 6.68 (d, J = 2.5 Hz, 1H), 5.49 (s, 1H), 2.54 (s, 3H).






835
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ13.13 (s, 1H), 8.11 (d, J = 2.5 Hz, 1H), 6.97 (d, J = 2.5 Hz, 1H), 6.9O (s, 1H), 1.61 (s, 9H).






836
CF3


embedded image








837
CF3


embedded image








838
CF3


embedded image








839
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.25 (s, 1H), 8.53 (s, 1H), 8.18 (s, 1H), 7.23 (s, 1H), 3.92 (s, 3H).






840
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.83 (s, 1H), 8.56 (s, 1H), 8.20 (s, 1H), 7.20 (s, 1H), 4.22 (q, J = 7.2 Hz, 2H), 1.40 (t, J = 7.2 Hz, 3H).






841
CF3


embedded image








842
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.66 (s, 1H), 8.44 (s, 1H), 7.22 (s, 1H), 3.83 (s, 3H), 3.31 (s, 3H).






843
CF3


embedded image








844
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) 13.52 (s, 1H), 8.99 (s, 1H), 8.50 (s, 1H), 7.92 (t, J = 58.5 Hz, 1H), 7.23 (s, 1H).






845
CF3


embedded image








846
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.27 (br, 1H), 8.68 (s, 1H), 8.24 (s, 1H), 7.72- 6.70 (m, 6H), 5.43 (s, 2H).






847
CF3


embedded image








848
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.87 (s, 1H), 7.81 (s, 1H), 7.19 (s, 1H), 6.97 (s, 1H), 5.36 (t, J = 6.8 Hz, 1H), 3.90- 3.77 (m, 2H), 2.13-2.01 (m, 2H), 1.85- 1.68 (m, 2H), 1.67-1.50 (m, 2H).






849
CF3


embedded image








850
CF3


embedded image








851
CF3


embedded image








852
CF3


embedded image



1H NMR (500 MHz, DMSO-d) δ 12.84 (s, 1H), 8.68 (s, 1H), 8.27 (s, 1H), 7.22 (s, 1H), 5.67 (q, J = 6.0 Hz, 1H), 3.45 (q, J = 7.0 Hz, 1H), 3.21 (dq, J = 14.2, 7.0 Hz, 1H), 1.62 (d, J = 6.0 Hz, 3H), 1.03 (t, J = 7.0 Hz, 3H).






853
CF3


embedded image








854
CF3


embedded image








855
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.54 (s, 1H), 7.72 (s, 1H), 7.45 (s, 1H), 6.87 (s, 1H), 3.68 (s, 3H).






856
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.93 (s, 1H), 7.40 (d, J = 2.5 Hz, 1H), 7.10 (d, J = 2.5 Hz, 1H), 6.87 (s, 1H), 3.94 (s, 3H).






857
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.24 (s, 1H), 7.75 (s, 1H), 7.58 (s, 1H), 6.91 (s, 1H), 3.79 (s, 3H).






858
CF3


embedded image








859
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.00 (s, 1H), 6.89 (s, 1H), 4.19 (s, 3H).






860
CF3


embedded image








861
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ13.13 (s, 1H), 8.26 (s, 1H), 8.00 (s, 1H), 6.88 (s, 1H).






862
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.60 (s, 1H), 8.23 (d, J = 2.0 Hz, 1H), 7.41 (d, J = 2.0 Hz, 1H), 6.89 (s, 1H).






863
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.86 (br, 1H), 7.26 (s, 1H), 2.38 (s, 3H), 2.20 (s, 3H).






864
CF3


embedded image








865
CF3


embedded image








866
CF3


embedded image








867
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.66 (s, 1H), 8.05 (d, J = 2.5 Hz, 1H), 7.56 (d, J = 2.5 Hz, 1H), 6.88 (s, 1H).






868
CF3


embedded image








869
CF3


embedded image








870
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.83 (s, 1H), 9.24 (s, 1H), 8.24 (s, 1H), 6.89 (s, 1H).






871
CF3


embedded image








872
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.70 (s, 1H), 7.94 (s, 1H), 6.84 (s, 1H).






873
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.26 (br, 1H), 7.35 (s, 1H), 7.29 (s, 1H), 4.08 (s, 3H).






874
CF3


embedded image








875
CF3


embedded image








876
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.86 (s, 1H), 9.07 (s, 1H), 8.50 (d, J = 6.5 Hz, 1H), 7.70 (d, J = 7.5 Hz, 1H), 7.50- 7.34 (m, 2H), 7.21 (s, 1H).






877
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.91 (s, 1H), 7.63 (d, J = 8.0 Hz, 1H), 7.54 (s, 1H), 7.51 (d, J = 8.0 Hz, 1H), 7.25 (s, 1H), 7.17 (m, 1H), 7.00 (m, 1H).






878
CF3


embedded image








879
CF3


embedded image








880
CF3


embedded image








881
CF3


embedded image








882
CF3


embedded image








883
CF3


embedded image








884
CF3


embedded image








885
CF3


embedded image








886
CF3


embedded image








887
CF3


embedded image








888
CF3


embedded image








889
CF3


embedded image








890
CF3


embedded image








891
CF3


embedded image








892
CF3


embedded image








893
CF3


embedded image








894
CF3


embedded image








895
CF3


embedded image








896
CF3


embedded image








897
CF3


embedded image








898
CF3


embedded image








899
CF3


embedded image








900
CF3


embedded image








901
CF3


embedded image








902
CF3


embedded image








903
CF3


embedded image








904
CF3


embedded image








905
CF3


embedded image








906
CF3


embedded image








907
CF3


embedded image








908
CF3


embedded image








909
CF3


embedded image








910
CF3


embedded image








911
CF3


embedded image








912
CF3


embedded image








913
CF3


embedded image








914
CF3


embedded image








915
CF3


embedded image








916
CF3


embedded image








917
CF3


embedded image








918
CF3


embedded image








919
CF3


embedded image








920
CF3


embedded image








921
CF3


embedded image








922
CF3


embedded image








923
CF3


embedded image








924
CF3


embedded image








925
CF3


embedded image








926
CF3


embedded image








927
CF3


embedded image








928
CF3


embedded image








929
CF3


embedded image








930
CF3


embedded image








931
CF3


embedded image








932
CF3


embedded image








933
CF3


embedded image








934
CF3


embedded image








935
CF3


embedded image








936
CF3


embedded image








937
CF3


embedded image








938
CF3


embedded image








939
CF3


embedded image








940
CF3


embedded image








941
CF3


embedded image








942
CF3


embedded image








943
CF3


embedded image








944
CF3


embedded image








945
CF3


embedded image








946
CF3


embedded image








947
CF3


embedded image








948
CF3


embedded image








949
CF3


embedded image








950
CF3


embedded image








951
CF3


embedded image








952
CF3


embedded image








953
CF3


embedded image








954
CF3


embedded image








955
CF3


embedded image








956
CF3


embedded image








957
CF3


embedded image








958
CF3


embedded image








959
CF3


embedded image








960
CF3


embedded image








961
CF3


embedded image








962
CF3


embedded image








963
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.59 (s, 1H), 8.66 (d, J = 1.5 Hz, 1H), 8.36 (dd, J = 8.0, 1.5 Hz, 1H), 7.66 (m, 1H), 7.24 (s, 1H).






964
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.67 (s, 1H), 8.84 (d, J = 5.0 Hz, 1H), 8.58 (m, 1H), 7.23 (s, 1H), 7.17 (dd, J = 8.0, 5.0 Hz, 1H).






965
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.98 (s, 1H), 8.46 (dd, J = 5.0, 1.5 Hz, 1H), 7.99 (dd, J = 8.0, 1.5 Hz, 1H), 7.61 (dd, J = 8.1, 5.0 Hz, 1H), 7.28 (s, 1H).






966
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.62 (s, 1H), 8.99 (d, J = 2.5 Hz, 1H), 8.34 (dd, J = 8.5, 2.5 Hz, 1H), 7.81 (d, J = 8.5 Hz, 1H), 7.3O (s, 1H).






967
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.73 (s, 1H), 9.14 (s, 1H), 8.82 (s, 1H), 8.59 (s, 1H), 7.32 (s, 1H).






968
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.66 (s, 1H), 8.82 (s, 1H), 8.56 (d, J = 5.0 Hz, 1H), 7.68 (d, J = 5.0 Hz, 1H), 7.28 (s, 1H)






969
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.12 (s, 1H), 8.26 (dd, J = 5.0, 1.5 Hz, 1H), 7.77 (dd, J = 8.0, 1.5 Hz, 1H), 7.50 (dd, J = 8.0, 5.0 Hz, 1H), 7.26 (s, 1H).






970
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.87 (s, 1H), 8.59 (d, J = 1.0 Hz, 1H), 7.82 (d, J = 7.5 Hz, 1H), 7.70 (dd, J = 7.5, 1.0 Hz, 1H), 7.28 (s, 1H)






971
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.17 (s, 1H), 8.99 (d, J = 1.0 Hz, 1H), 8.87 (d, J = 1.0 Hz, 1H), 8.31 (s, 1H), 7.23 (s, 1H).






972
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.97 (s, 1H), 8.61 (s, 1H), 8.32 (d, J = 5.0 Hz, 1H), 7.80 (d, J = 5.0 Hz, 1H), 7.29 (s, 1H).






973
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ13.62 (s, 1H), 8.55 (dd, J = 5.0, 1.5 Hz, 1H), 7.76 (dd, J = 7.5, 1.5 Hz, 1H), 7.35 (dd, J = 7.5, 5.0 Hz, 1H), 7.30 (s, 1H), 2.32 (s, 3H).






974
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.41 (s, 1H), 9.07 (d, J = 2.0 Hz, 1H), 8.30 (dd, J = 8.0, 2.0 Hz, 1H), 7.41 (d, J = 8.0 Hz, 1H), 7.26 (s, 1H), 2.54 (s, 3H).






975
CF3


embedded image



1H NMR (500 MHz, Chloroform-d) δ 8.73 (s, 1H), 8.61 (d, J = 5.0 Hz, 1H), 7.26 (d, J = 5.0 Hz, 1H), 6.94 (s, 1H), 5.64 (s, 1H), 2.36 (s, 3H).






976
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.78 (s, 1H), 8.93-8.92 (m, 1H), 8.49-8.45 (m, 1H), 8.34-8.33 (m, 1H), 7.35 (s, 1H).






977
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.65 (s, 1H), 9.44 (s, 1H), 9.10 (s, 1H), 8.75 (s, 1H), 7.33 (s, 1H).






978
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.88 (s, 1H), 8.85 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 7.58-7.53 (m, 1H), 7.28 (s, 1H).






979
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.37 (s, 1H), 8.85 (dd, J = 5.0, 1.5 Hz, 1H), 8.22 (dd, J = 8.1, 1.5 Hz, 1H), 7.92 (dd, J = 7.9, 5.0 Hz, 1H), 7.28 (s, 1H).






980
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.27 (s, 1H), 9.09 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 7.86 (d, J = 5.0 Hz, 1H), 7.25 (s, 1H).






981
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 8.84 (d, J = 2.5 Hz, 1H), 8.22 (dd, J = 8.5, 2.5 Hz, 1H), 7.16 (s, 1H), 6.76 (s, 2H), 6.62 (d, J = 8.5 Hz, 1H).






982
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 8.47 (s, 1H), 7.99 (s, 1H), 7.75 (s, 1H), 7.15 (s, 1H).






983
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.53 (s, 1H), 9.31 (d, J = 2.0 Hz, 1H), 8.63 (dd, J = 8.0, 2.0 Hz, 1H), 8.18 (d, J = 8.0 Hz, 1H), 7.33 (s, 1H).






984
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.84 (s, 1H), 9.40 (s, 1H), 9.14 (s, 1H), 8.84 (s, 1H), 7.34 (s, 1H).






985
CF3


embedded image








986
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.02 (s, 1H), 8.43-8.35 (dd, J = 8.0, 1.0 Hz, 1H), 7.84-7.81 (m, 1H), 7.24 (s, 1H).






987
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.22 (s, 1H), 8.45-8.41 (m, 1H), 7.25-7.18 (m, 2H).






988
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.14 (s, 1H), 8.58-8.43 (m, 1H), 7.91-7.88 (m, 1H), 7.24 (s, 1H).






989
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.02 (s, 1H), 8.76-8.63 (m, 1H), 7.24 (s, 1H), 7.01 (m, 1H).






990
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.22 (s, 1H), 8.66-8.42 (m, 1H), 8.35-8.23 (m, 1H), 7.36 (s, 1H).






991
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.15 (s, 1H), 8.16 (d, J = 8.0 Hz, 1H), 7.43 (d, J = 8.0 Hz, 1H), 7.24 (s, 1H).






992
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.01 (s, 1H), 8.60 (d, J = 1.5 Hz, 1H), 8.12 (d, J = 1.5 Hz, 1H), 7.24 (s, 1H).






993
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.08 (s, 1H), 8.59 (d, J = 5.0 Hz, 1H), 7.59 (d, J = 5.0 Hz, 1H), 7.24 (s, 1H).






994
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.99 (s, 1H), 8.95 (d, J = 1.5 Hz, 1H), 8.23 (d, J = 1.5 Hz, 1H), 7.24 (s, 1H).






995
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.41 (s, 1H), 8.88 (s, 1H), 7.68 (s, 1H), 7.24 (s, 1H).






996
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.25 (s, 1H), 8.77 (d, J = 1.5 Hz, 1H), 8.49 (d, J = 1.5 Hz, 1H), 7.24 (s, 1H).






997
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.38 (s, 1H), 8.29 (dd, J = 8.5, 7.5 Hz, 1H), 7.71 (d, J = 7.5 Hz, 1H), 7.36 (s, 1H).






998
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.31 (s, 1H), 8.43 (dd, J = 7.5, 1.0 Hz, 1H), 8.21 (dd, J = 5.0, 1.0 Hz, 1H), 7.24 (s, 1H).






999
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.22 (s, 1H), 8.42 (dd, J = 6.0, 5.0 Hz, 1H), 7.50 (d, J = 5.0 Hz, 1H), 7.23 (s, 1H).






1000
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.45 (s, 1H), 8.79 (dd, J = 6.5, 1.0 Hz, 1H), 8.30 (dd, J = 5.0, 1.0 Hz, 1H), 7.24 (s, 1H).






1001
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.88 (s, 1H), 8.71 (d, J = 5.5 Hz, 1H), 7.31 (d, J = 7.5 Hz, 1H), 7.24 (s, 1H).






1002
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.13 (s, 1H), 8.55 (s, 1H), 8.36 (d, J = 8.0 Hz, 1H), 7.24 (s, 1H).






1003
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.17 (s, 1H), 8.27 (dd, J = 8.0, 5.0 Hz, 1H), 7.24 (s, 1H), 7.07 (dd, J = 9.5, 8.0 Hz, 1H).






1004
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.05 (s, 1H), 8.60 (dd, J = 8.0, 1.0 Hz, 1H), 7.74 (dd, J = 5.5, 1.0 Hz, 1H), 7.24 (s, 1H).






1005
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.09 (s, 1H), 8.62 (dd, J = 6.5, 5.0 Hz, 1H), 7.30 (dd, J = 8.0, 5.0 Hz, 1H), 7.23 (s, 1H).






1006
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.18 (s, 1H), 8.75 (d, J = 1.0 Hz, 1H), 7.83 (dd, J = 8.0, 1.0 Hz, 1H), 7.24 (s, 1H).






1007
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.27 (s, 1H), 8.93 (d, J = 5.0 Hz, 1H), 7.38 (d, J = 8.0 Hz, 1H), 7.23 (s, 1H).






1008
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.57 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.47 (d, J = 4.0 Hz, 1H), 7.36 (s, 1H).






1009
CF3


embedded image








1010
CF3


embedded image








1011
CF3


embedded image








1012
CF3


embedded image








1013
CF3


embedded image








1014
CF3


embedded image








1015
CF3


embedded image








1016
CF3


embedded image








1017
CF3


embedded image








1018
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.15 (s, 1H), 8.36 (s, 1H), 7.57 (s, 1H), 7.34 (s, 1H), 2.20 (s, 3H).






1019
CF3


embedded image








1020
CF3


embedded image








1021
CF3


embedded image








1022
CF3


embedded image








1023
CF3


embedded image








1024
CF3


embedded image








1025
CF3


embedded image








1026
CF3


embedded image








1027
CF3


embedded image








1028
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.70 (s, 1H), 8.14 (d, J = 2.0 Hz, 1H), 7.58 (d, J = 2.0 Hz, 1H), 7.24 (s, 1H), 5.18 (s, 2H), 3.91 (s, 3H).






1029
CF3


embedded image








1030
CF3


embedded image








1031
CF3


embedded image








1032
CF3


embedded image








1033
CF3


embedded image








1034
CF3


embedded image








1035
CF3


embedded image








1036
CF3


embedded image








1037
CF3


embedded image








1038
CF3


embedded image








1039
CF3


embedded image








1040
CF3


embedded image








1041
CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.13 (s, 1H), 8.89 (d, J = 2.5 Hz, 1H), 8.24 (dd, J = 9.0, 2.5 Hz, 1H), 7.19 (s, 1H), 6.94 (d, J = 9.0 Hz, 1H), 3.65-3.55 (m, 4H), 3.42 (s, 4H), 1.41 (s, 9H).






1042
CF3


embedded image








1043
CF3


embedded image








1044
CF3


embedded image








1045
CF3


embedded image








1046
CF3


embedded image








1047
CF3


embedded image








1048
CF3


embedded image








1049
CF3


embedded image








1050
CF3


embedded image








1051
CF3


embedded image








1052
CF3


embedded image








1053
CF3


embedded image








1054
CF3


embedded image








1055
CF3


embedded image








1056
CF3


embedded image








1057
CF3


embedded image








1058
CF3


embedded image








1059
CF3


embedded image








1060
CF3


embedded image








1061
CF3


embedded image








1062
CF3


embedded image








1063
CF3


embedded image








1064
CF3


embedded image








1065
CF3


embedded image








1066
CF3


embedded image








1067
CF3


embedded image








1068
CF3


embedded image








1069
CF3


embedded image








1070
CF2CF3


embedded image








1071
CF2CF3


embedded image








1072
CF2CF3


embedded image








1073
CH2F


embedded image








1074
CH2F


embedded image








1075
CH2F


embedded image








1076
CH2F


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.15 (s, 1H), 8.43-8.33 (m, 1H), 7.99-7.80 (m, 1H), 7.74-7.55 (m, 1H), 6.95 (s, 1H), 5.40 (d, J = 65.0 Hz, 2H).






1077
CH2F


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.18 (s, 1H), 8.73 (dd, J = 4.5, 1.5 Hz, 1H), 7.80-7.71 (m, 2H), 6.96 (s, 1H), 5.40 (d, J = 65.0 Hz, 2H), 1.87-1.81 (m, 1H), 0.77-0.65 (m, 2H), 0.62-0.55 (m, 2H).






1078
CH2F


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.00 (s, 1H), 8.47 (dd, J = 5.5, 1.0 Hz, 1H), 8.14 (dd, J = 7.0, 1.0 Hz, 1H), 7.04 (s, 1H), 5.40 (d, J = 65.0 Hz, 2H), 3.07 (q, J = 9.0 Hz, 2H).






1079
CH2F


embedded image








1080
CH2F


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.18 (s, 1H), 8.26 (dd, J = 8.0, 5.0 Hz, 1H), 7.82 (d, J = 8.0 Hz, 1H), 6.96 (s, 1H), 6.60 (t, J = 73.5 Hz, 1H), 5.30 (s, 1H).






1081
CF2CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.05 (s, 1H), 8.43-8.35 (m, 1H), 8.04-7.90 (m, 1H), 7.75-7.61 (m, 1H), 7.00 (s, 1H).






1082
CF2CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 12.97 (s, 1H), 9.16 (d, J = 1.5 Hz, 1H), 8.18 (dd, J = 8.0, 1.5 Hz, 1H), 7.74 (d, J = 8.0 Hz, 1H), 6.96 (s, 1H), 3.00 (d, J = 7.0 Hz, 2H), 1.73-1.52 (m, 4H), 1.56- 1.37 (m, 2H), 1.33-1.14 (m, 5H).






1083
CF2CF3


embedded image



1H NMR (500 MHz, DMSO-d6) δ 13.14 (s, 1H), 8.81 (s, 1H), 6.89 (s, 1H), 2.98 (t, J = 7.5 Hz, 2H), 1.70-1.55 (m, 2H), 0.92 (t, J = 8.0 Hz, 3H).






1084
CH2F


embedded image








1085
CHF2


embedded image








1086
CHF2


embedded image








1087
CH2F


embedded image








1088
CH2F


embedded image








1089
CHF2


embedded image








1090
CHF2


embedded image








1091
CHF2


embedded image








1092
CF2CF3


embedded image








1093
CF2CF3


embedded image








1094
CF2CF3


embedded image








1095
CF2CF3


embedded image








1096
CF2CF3


embedded image








1097
CF2CF3


embedded image








1098
CF3


embedded image








1099
CF3


embedded image








1100
CF3


embedded image








1101
CF3


embedded image








1102
CF3


embedded image








1103
CF3


embedded image








1104
CF3


embedded image








1105
CF3


embedded image








1106
CF3


embedded image








1107
CF3


embedded image








1108
CF3


embedded image








1109
CF3


embedded image








1110
CF3


embedded image








1111
CF3


embedded image








1112
CF3


embedded image








1113
CF3


embedded image








1114
CF3


embedded image








1115
CF3


embedded image








1116
CF3


embedded image








1117
CF3


embedded image








1118
CF3


embedded image








1119
CF3


embedded image








1120
CF3


embedded image








1121
CF3


embedded image








1122
CF3


embedded image








1123
CF3


embedded image








1124
CF3


embedded image








1125
CF3


embedded image








1126
CF3


embedded image








1127
CF3


embedded image








1128
CF3


embedded image








1129
CF3


embedded image








1130
CF3


embedded image








1131
CF3


embedded image








1132
CF3


embedded image








1133
CF3


embedded image








1134
CF3


embedded image








1135
CF3


embedded image








1136
CF3


embedded image








1137
CF3


embedded image








1138
CF3


embedded image








1139
CF3


embedded image








1140
CF3


embedded image








1141
CF3


embedded image








1142
CF3


embedded image








1143
CF3


embedded image








1144
CF3


embedded image








1145
CF3


embedded image








1146
CF3


embedded image








1147
CF3


embedded image








1148
CF3


embedded image








1149
CF3


embedded image








1150
CF3


embedded image








1151
CF3


embedded image








1152
CF3


embedded image








1153
CF3


embedded image








1154
CF3


embedded image








1155
CF3


embedded image








1156
CF3


embedded image








1157
CF3


embedded image








1158
CF3


embedded image








1159
CF3


embedded image








1160
CF3


embedded image








1161
CF3


embedded image








1162
CF3


embedded image








1163
CF3


embedded image








1164
CF3


embedded image








1165
CF3


embedded image








1166
CF3


embedded image








1167
CF3


embedded image








1168
CF3


embedded image








1169
CF3


embedded image








1170
CF3


embedded image








1171
CF3


embedded image








1172
CF3


embedded image








1173
CF3


embedded image








1174
CF3


embedded image








1175
CF3


embedded image








1176
CF3


embedded image








1177
CF3


embedded image








1178
CF3


embedded image








1179
CF3


embedded image








1180
CF3


embedded image








1181
CF3


embedded image








1182
CF3


embedded image








1183
CF3


embedded image








1184
CF3


embedded image








1185
CF3


embedded image








1186
CF3


embedded image








1187
CF3


embedded image








1188
CF3


embedded image








1189
CF3


embedded image








1190
CF3


embedded image








1191
CF3


embedded image








1192
CF3


embedded image








1193
CF3


embedded image








1194
CF3


embedded image








1195
CF3


embedded image








1196
CF3


embedded image








1197
CF3


embedded image








1198
CF3


embedded image








1199
CF3


embedded image








1200
CF3


embedded image








1201
CF3


embedded image








1202
CF3


embedded image








1203
CF3


embedded image








1204
CF3


embedded image








1205
CF3


embedded image








1206
CF3


embedded image








1207
CF3


embedded image








1208
CF3


embedded image








1209
CF3


embedded image








1210
CF3


embedded image








1211
CF3


embedded image








1212
CF3


embedded image








1213
CF3


embedded image








1214
CF3


embedded image








1215
CF3


embedded image








1216
CF3


embedded image








1217
CF3


embedded image








1218
CF3


embedded image








1219
CF3


embedded image








1220
CF3


embedded image








1221
CF3


embedded image








1222
CF3


embedded image








1223
CF3


embedded image








1224
CF3


embedded image








1225
CF3


embedded image








1226
CF3


embedded image








1227
CF3


embedded image








1228
CF3


embedded image








1229
CF3


embedded image








1030
CF3


embedded image








1231
CF3


embedded image








1232
CF3


embedded image








1233
CF3


embedded image








1234
CF3


embedded image








1235
CF3


embedded image








1236
CF3


embedded image








1237
CF3


embedded image








1238
CF3


embedded image








1239
CF3


embedded image








1240
CF3


embedded image








1241
CF3


embedded image








1242
CF3


embedded image








1243
CF3


embedded image








1244
CF3


embedded image








1245
CF3


embedded image








1246
CF3


embedded image








1247
CF3


embedded image








1248
CF3


embedded image








1249
CF3


embedded image








1250
CF3


embedded image








1251
CF3


embedded image








1252
CF3


embedded image








1253
CF3


embedded image








1254
CF3


embedded image








1255
CF3


embedded image








1256
CF3


embedded image








1257
CF3


embedded image








1258
CF3


embedded image








1259
CF3


embedded image








1260
CF3


embedded image








1261
CF3


embedded image








1262
CF3


embedded image








1263
CF3


embedded image








1264
CF3


embedded image








1265
CF3


embedded image








1266
CF3


embedded image








1267
CF3


embedded image








1268
CF3


embedded image








1269
CF3


embedded image








1270
CF3


embedded image








1271
CF3


embedded image








1272
CF3


embedded image








1273
CF3


embedded image








1274
CF3


embedded image








1275
CF3


embedded image








1276
CF3


embedded image








1277
CF3


embedded image








1278
CF3


embedded image








1279
CF3


embedded image








1280
CF3


embedded image








1281
CF3


embedded image








1282
CF3


embedded image








1283
CF3


embedded image








1284
CF3


embedded image








1285
CF3


embedded image








1286
CF3


embedded image



1H NMR (500 MHz, Chloroform-d) 7.25 (d, J = 2.0 Hz, 1H), 7.19 (dd, J = 7.5, 2.0 Hz, 1H), 7.06-6.91 (m, 2H), 5.52 (s, 1H).






1287
CF3


embedded image



1H NMR (500 MHz, Chloroform-d) 7.83 (d, J = 7.5 Hz, 2H), 7.59 (d, J = 7.5 Hz, 2H), 7.10 (s, 1H), 5.88 (s, 1H), 0.25 (s, 9H).






1288
CF3


embedded image








1289
CF3


embedded image








1290
CF3


embedded image








1291
CF3


embedded image








1292
CF3


embedded image








1293
CF3


embedded image








1294
CF3


embedded image








1295
CF3


embedded image








1296
CF3


embedded image








1297
CF3


embedded image








1298
CF3


embedded image








1299
CF3


embedded image








1300
CF3


embedded image








1301
CF3


embedded image








1302
CF3


embedded image








1303
CF3


embedded image








1304
CF3


embedded image








1305
CF3


embedded image








1306
CF3


embedded image








1307
CF3


embedded image








1308
CF3


embedded image








1309
CF3


embedded image








1310
CF3


embedded image








1311
CF3


embedded image








1312
CF3


embedded image








1313
CF3


embedded image








1314
CF3


embedded image








1315
CF3


embedded image








1316
CF3


embedded image








1317
CF3


embedded image








1318
CF3


embedded image








1319
CF3


embedded image








1320
CF3


embedded image








1321
CF3


embedded image








1322
CF3


embedded image








1323
CF3


embedded image








1324
CF3


embedded image








1325
CF3


embedded image








1326
CF3


embedded image








1327
CF3


embedded image








1328
CF3


embedded image








1329
CF3


embedded image








1330
CF3


embedded image








1331
CF3


embedded image








1332
CF3


embedded image








1333
CF3


embedded image








1334
CF3


embedded image








1335
CF3


embedded image








1336
CF3


embedded image








1337
CF3


embedded image








1338
CF3


embedded image








1339
CF3


embedded image








1340
CF3


embedded image








1341
CF3


embedded image








1342
CF3


embedded image








1343
CF3


embedded image








1344
CF3


embedded image








1345
CF3


embedded image








1346
CF3


embedded image








1347
CF3


embedded image








1348
CF3


embedded image








1349
CF3


embedded image








1350
CF3


embedded image








1351
CF3


embedded image








1352
CF3


embedded image








1353
CF3


embedded image








1354
CF3


embedded image








1355
CF3


embedded image








1356
CF3


embedded image








1357
CF3


embedded image








1358
CF3


embedded image








1359
CF3


embedded image








1360
CF3


embedded image








1361
CF3


embedded image








1362
CF3


embedded image








1363
CF3


embedded image








1364
CF3


embedded image








1365
CF3


embedded image








1366
CF3


embedded image








1367
CF3


embedded image








1368
CF3


embedded image








1369
CF3


embedded image








1370
CF3


embedded image








1371
CF3


embedded image








1372
CF3


embedded image








1373
CF3


embedded image








1374
CF3


embedded image








1375
CF3


embedded image








1376
CF3


embedded image








1377
CF3


embedded image








1378
CF3


embedded image








1379
CF3


embedded image








1380
CF3


embedded image








1381
CF3


embedded image








1382
CF3


embedded image








1383
CF3


embedded image








1384
CF3


embedded image








1385
CF3


embedded image








1386
CF3


embedded image








1387
CF3


embedded image








1388
CF3


embedded image








1389
CF3


embedded image








1390
CF3


embedded image








1391
CF3


embedded image








1392
CF3


embedded image








1393
CF3


embedded image








1394
CF3


embedded image








1395
CF3


embedded image








1396
CF3


embedded image








1397
CF3


embedded image








1398
CF3


embedded image








1399
CF3


embedded image








1400
CF3


embedded image








1401
CF3


embedded image








1402
CF3


embedded image








1403
CF3


embedded image








1404
CF3


embedded image








1405
CF3


embedded image








1406
CF3


embedded image








1407
CF3


embedded image








1408
CF3


embedded image








1409
CF3


embedded image








1410
CF3


embedded image








1411
CF3


embedded image








1412
CF3


embedded image








1413
CF3


embedded image








1414
CF3


embedded image








1415
CF3


embedded image








1416
CF3


embedded image








1417
CF3


embedded image








1418
CF3


embedded image








1419
CF3


embedded image








1420
CF3


embedded image








1421
CF3


embedded image








1422
CF3


embedded image








1423
CF3


embedded image








1424
CF3


embedded image








1425
CF3


embedded image








1426
CF3


embedded image








1427
CF3


embedded image








1428
CF3


embedded image








1429
CF3


embedded image








1430
CF3


embedded image








1431
CF3


embedded image








1432
CF3


embedded image








1433
CF3


embedded image








1434
CF3


embedded image








1435
CF3


embedded image








1436
CF3


embedded image








1437
CF3


embedded image








1438
CF3


embedded image








1439
CF3


embedded image








1440
CF3


embedded image








1441
CF3


embedded image








1442
CF3


embedded image








1443
CF3


embedded image








1444
CF3


embedded image








1445
CF3


embedded image








1446
CF3


embedded image








1447
CF3


embedded image








1448
CF3


embedded image








1449
CF3


embedded image








1450
CF3


embedded image








1451
CF3


embedded image








1452
CF3


embedded image








1453
CF3


embedded image








1454
CF3


embedded image








1455
CF3


embedded image








1456
CF3


embedded image








1457
CF3


embedded image








1458
CF3


embedded image








1459
CF3


embedded image








1460
CF3


embedded image








1461
CF3


embedded image








1462
CF3


embedded image








1463
CF3


embedded image








1464
CF3


embedded image








1465
CF3


embedded image








1466
CF3


embedded image








1467
CF3


embedded image








1468
CF3


embedded image








1469
CF3


embedded image








1470
CF2CF3


embedded image








1471
CH2F


embedded image








1472
CHF2


embedded image








1473
CF2CF3


embedded image








1474
CHF2


embedded image








1475
CHF2


embedded image








1476
CF2CF3


embedded image








1477
CH2F


embedded image








1478
OCHF2


embedded image








1479
CF2CF3


embedded image








1480
CF2CF3


embedded image








1481
CF2CF3


embedded image








1482
CF2CF3


embedded image








1483
Ph


embedded image








1484
CF2CF3


embedded image








1485
CF2CF3


embedded image








1486
CF2CF3


embedded image








1487
CN


embedded image








1488
CF2CF3


embedded image








1489
CF2CF3


embedded image








1490
CF2CF3


embedded image








1491
CF2CF3


embedded image








1492
CF2CF3


embedded image








1493
CF3


embedded image



1H NMR (500 MHz, Chloroform-d) 7.16 (s, 1H), 5.85 (s, 1H), 4.27 (s, 3H).






1494
CF3


embedded image








1495
CF3


embedded image








1496
CF3


embedded image








1497
CF3


embedded image








1498
CF3


embedded image








1499
CF3


embedded image








1500
CF3


embedded image








1501
CF3


embedded image








1502
CF3


embedded image








1503
CF3


embedded image








1504
CF3


embedded image








1505
CF3


embedded image








1506
CF3


embedded image








1507
CONH2


embedded image








1508
CF3


embedded image








1509
CF3


embedded image








1510
CF3


embedded image








1511
CF3


embedded image








1512
CF3


embedded image



1H NMR (500 MHz, Chloroform-d) 7.34 (s, 1H), 7.08 (s, 1H), 7.04 (s, 1H), 5.78 (s, 1H), 5.53 (s, 1H).






1513
Ph


embedded image








1514
CF3


embedded image








1515
CF3


embedded image








1516
NH2


embedded image








1517
CF3


embedded image








1518
CF3


embedded image








1519
CF3


embedded image








1520
CF3


embedded image








1521
CF3


embedded image








1522
CF3


embedded image



1H NMR (500 MHz, Chloroform-d) δ 7.74 (d, J = 15.0 Hz, 1H), 7.00 (s, 1H), 6.50 (d, J = 15.0 Hz, 1H), 5.87 (s, 1H), 4.24 (q, J = 8.0 Hz, 2H), 1.31 (t, J = 8.0 Hz, 3H).






1523
CF3


embedded image



1H NMR (500 MHz, Chloroform-d) δ 6.99 (s, 1H), 6.25 (s, 1H), 5.87 (s, 1H), 1.78 (s, 6H).






1524
CF3


embedded image



1H NMR (500 MHz, Chloroform-d) δ 7.07 (s, 1H), 6.07-5.96 (m, 1H), 5.87 (s, 1H), 2.03-1.93 (m, 4H), 1.66-1.56 (m, 4H).






1525
CF3
Me
(500 MHz, Chloroform-7) 5 6.96 (s, 1H), 5.87 (s, 1H), 2.10 (s, 3H).





1526
CF3


embedded image








1527
OH


embedded image








1528
CF3


embedded image


(500 MHz, Chloroform-d) δ 6.95 (s, 1H), 6.38-6.31 (m, 1H), 5.87 (s, 1H), 2.35-2.24 (m, 4H), 1.82-1.70 (m, 2H).





1529
CF3


embedded image


(500 MHz, Chloroform-d) δ 6.99 (s, 1H), 5.87 (s, 1H), 5.65-5.42 (m, 1H), 4.31-4.22 (m, 2H), 2.62-2.54 (m, 2H).





1530
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.03 (s, 1H), 6.22 (d, J = 15.0 Hz, 1H), 5.93- 5.85 (m, 2H), 0.08 (s, 9H).





1531
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.09 (s, 1H), 5.87 (s, 1H), 5.81-5.74 (m, 1H), 4.20-4.04 (m, 2H), 3.79-3.66 (m, 2H), 2.13-2.01 (m, 2H).





1532
CF3


embedded image


(500 MHz, Chloroform-d) δ 7.03 (s, 1H), 6.40-6.26 (m, 2H), 5.87 (s, 1H), 2.07-1.97 (m, 2H), 1.46-1.32 (m, 2H), 0.95 (t, J = 8.0 Hz, 3H).





1533
CF3
Et
(500 MHz, Chloroform-d) δ 6.96 (s, 1H), 5.87 (s, 1H), 2.41 (q, J = 8.0 Hz, 2H), 1.16 (t, J = 8.0 Hz, 3H).





1534
OCF3


embedded image








1535
CF3


embedded image








1536
CN


embedded image








1537
CF3


embedded image








1538
CF3


embedded image








1539
CF3


embedded image








1540
CF3


embedded image








1541
CF3


embedded image








1542
CF3


embedded image








1543
CF2CF3


embedded image








1544
CF3


embedded image








1545
CF3


embedded image








1546
CF3


embedded image








1547
CHF2


embedded image








1548
CF3


embedded image








1549
CF3


embedded image









text missing or illegible when filed















TABLE 2







Structure and 1HNMR data of the derivative Compound 1-1


I-1




embedded image
















No.
X
M
A

1HNMR






1-1
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.43-7.27 (m, 3H), 7.15- 7.02 (m, 2H), 2.47 (s, 3H).





1-2
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.47-7.39 (m, 2H), 7.18 (s, 1H), 7.11-7.03 (m, 2H), 2.47 (s, 3H).





1-3
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.45-7.33 (m, 2H), 7.20- 7.11 (m, 2H), 2.27 (q, 7 = 8.0 Hz, 1H), 1.12 (t, J = 8.0 Hz, 2H).





1-4
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.45-7.37 (m, 2H), 7.18 (s, 1H), 7.11-7.03 (m, 2H), 2.27 (q, J = 8.0 Hz, 2H), 1.03 (t, J = 8.0 Hz, 3H).





1-5
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.37-7.31 (m,2H),7.17(s, 1H), 6.84-6.78 (m, 2H), 2.78 (t, J = 8.0 Hz, 2H), 2.27 (s, 3H), 1.73- 1.62 (m, 2H), 1.38 (t, J = 8.0 Hz, 3H).





1-6
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.43-7.36 (m, 2H), 7.17 (s, 1H), 6.80-6.74 (m, 2H), 3.80 (s, 3H), 2.70 (hept, J = 6.5 Hz, 1H), 1.17 (d, J = 6.5 Hz, 6H).





1-7
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.63 (d, J = 2.0 Hz, 1H), 7.31 (dd, J = 7.5, 2.0 Hz, 1H), 7.26 (d, J = 7.5 Hz, 1H), 7.18 (s, 1H), 2.33 (t, J = 8.0 Hz, 2H), 1.53-1.41 (m, 4H), 0.92 (t, J = 8.0 Hz, 3H).





1-8
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.98-7.89 (m, 2H), 7.75- 7.63 (m, 2H),7.19(s, 1H), 4.08 (d, J = 7.0 Hz, 2H), 2.19- 2.02 (m, 1H), 0.97 (d,7 = 7.0 Hz, 6H).





1-9
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 9.13 (d, J = 1.5 Hz, 1H), 8.09 (dd, J = 8.0,1.5 Hz, 1H), 7.41 (d, J = 7.0 Hz, 2H), 1.16 (s, 9H).





1-10
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.92 (d, J = 7.5 Hz, 2H), 7.70 (d,7 = 7.5 Hz, 2H),7.18 (s, 1H), 2.33 (t, J = 8.0 Hz, 2H), 1.50-1.23 (m, 6H), 0.92 (t, J = 8.0 Hz, 3H).





1-11
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.96-7.90 (m, 2H), 7.90- 7.84 (m, 2H), 7.26 (s, 1H), 3.30 (s, 3H), 2.09 (s, 2H), 0.93 (s, 9H).





1-12
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.41-8.21 (m, 2H), 7.91- 7.60 (m, 2H),7.19(s, 1H), 2.14-1.77 (m, 3H), 1.75- 1.53 (m, 2H), 1.45-1.24 (m, 4H), 0.90 (t, J = 7.5 Hz, 3H), 0.79 (t, J = 8.0 Hz, 3H).





1-13
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.18-7.08 (m, 2H), 6.93- 6.68 (m, 2H), 6.62-6.47 (m, 1H), 4.13(s, 2H), 2.33 (t, J = 6.0 Hz, 2H), 1.51-1.22 (m, 8H), 0.93 (t, J = 8.0 Hz, 3H).





1-14
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.41-7.19 (m, 2H), 7.23- 7.10 (m, 2H), 2.33 (t, J = 8.0 Hz, 2H), 1.51-1.36 (m, 2H), 1.34-1.22 (m, 8H), 0.94 (t, J = 8.0 Hz, 3H).





1-15
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.62-7.52 (m, 2H), 7.46- 7.29 (m, 2H),7.14(s, 1H), 2.33 (t, J = 8.0 Hz, 2H), 1.51- 1.22 (m, 12H), 0.93 (t, J = 8.0 Hz, 3H).





1-16
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.47-7.39 (m, 2H), 7.11- 7.03 (m, 2H), 2.33 (t, J = 7.5 Hz, 2H), 1.51-1.22 (m, 22H), 0.89 (t, J = 8.0 Hz, 3H).





1-17
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.59-7.52 (m, 2H), 7.41- 7.31 (m, 3H), 2.33 (t, J = 7.5 Hz, 2H), 1.51-1.22 (m, 30H), 0.87 (t, J = 8.0 Hz, 3H).





1-18
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.70 (d, J = 7.5 Hz, 2H), 7.43 (d, J = 7.5 Hz, 2H), 7.13 (s, 1H), 4.08 (d, J = 7.0 Hz, 2H), 1.71-1.52 (m, 7H), 1.28- 1.17 (m, 2H).





1-19
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.53-7.45 (m, 2H), 7.46- 7.37 (m, 3H), 7.18 (s, 1H), 2.37-2.29 (m, 1H), 2.25- 2.14 (m, 2H), 1.82-1.63 (m, 5H), 1.53-1.40 (m,3H).





1-20
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.47-7.27 (m, 2H), 7.22- 7.14 (m, 1H), 7.17-7.00 (m, 2H), 5.54-5.42 (m, 1H), 1.87 -1.72(m, 3H).





1-21
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.39-7.32 (m, 2H), 7.32- 7.26 (m, 2H),7.14 (s, 1H), 2.75 (q, J = 8.0 Hz, 2H), 2.71- 2.61 (m, 2H), 1.21 (t, J = 8.0 Hz, 3H).





1-22
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.72-7.67 (m, 2H), 7.59- 7.52 (m, 2H),7.17 (s, 1H), 4.49 (q, J = 6.5 Hz, 1H), 1.72 (d, J = 6.5 Hz, 3H).





1-23
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.44-7.30 (m, 2H), 7.25- 7.17 (m, 2H), 3.28(t, J = 7.0 Hz, 2H), 2.33 (t, J = 7.5 Hz, 2H), 2.06-1.98 (m, 2H).





1-24
CF3


embedded image




embedded image








1-25
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.48-7.40 (m, 2H), 7.24 (s, 1H), 7.11-7.03 (m, 2H).





1-26
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.43-7.22 (m, 2H), 7.20- 7.11 (m,2H), 4.25 (q, J = 8.0 Hz, 2H), 1.26 (t, J = 8.0 Hz, 3H).





1-27
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.51-7.45 (m, 2H), 7.09- 7.03 (m, 2H), 4.23 (t, J = 7.5 Hz, 2H), 4.00 (t, J = 7.5 Hz, 2H), 1.87-1.50 (m, 6H), 1.02 (t, J = 8.0 Hz, 3H), 0.92 (t, J = 8.0 Hz, 3H).





1-28
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.50(d, J = 7.5Hz, 2H), 7.21 (s, 1H), 7.10 (d, J = 7.5 Hz, 2H), 5.15 (hept, J = 6.5 Hz, 1H), 2.77 (q, J = 7.5 Hz, 2H), 1.26-1.15 (m, 9H).





1-29
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.48-7.40 (m, 2H), 7.21 (s, 1H), 7.11-7.03 (m, 2H), 4.23 (t, J = 7.5 Hz, 2H), 1.60-1.40 (m, 4H), 0.98 (t, J = 8.0 Hz, 3H).





1-30
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.99-7.90 (m, 2H), 7.75- 7.69-7.61 (m, 2H), 7.22 (s, 1H), 4.05 (d, J = 7.0 Hz, 2H), 1.95- 1.80 (m, 1H), 0.95 (d, J = 6.5 Hz, 6H).





1-31
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.43-7.22 (m, 2H), 7.21- 7.11 (m, 2H), 4.23 (t, J = 7.5 Hz, 2H), 1.79-1.39 (m, 6H), 0.95 (t, J = 8.0 Hz, 3H).





1-32
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.36-7.28 (m, 2H), 7.20 (s, 1H), 7.13 (dd, J = 7.5, 1.0 Hz, 1H), 4.23 (t, J = 7.5 Hz, 2H), 2.30 (s, 3H), 2.20 (s, 3H), 1.78 -1.52 (m, 3H), 0.97 (d, J = 7.0 Hz, 6H).





1-33
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.96 (d, J = 2.5 Hz, 1H), 7.83 (dd, J = 7.5, 2.5 Hz, 1H), 7.48 (d, J = 7.5 Hz, 1H),7.22(s, 1H), 4.02 (s, 2H), 2.50 (s, 3H), 0.95 (s, 9H).





1-34
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.77 (d, J = 2.0 Hz, 1H), 8.57 (dd, J = 7.5, 2.0 Hz, 1H), 8.25 (d, J = 7.5 Hz, 1H),7.24(s, 1H), 1.61 (s, 6H), 1.49 (q, J = 8.0 Hz, 2H), 0.90 (t, J = 8.0 Hz, 3H).





1-35
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.05 (d, J = 2.0 Hz, 1H),7.80- 7.70 (m, 2H), 7.22 (s, 1H), 4.23 (t, J = 7.5 Hz, 2H), 1.72- 1.31 (m, 8H), 0.93 (t, J = 7.5 Hz, 3H).





1-36
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.08 (d, J = 2.0 Hz, 1H), 7.93 (dd, J = 7.5, 2.0 Hz, 1H), 7.82 (d, J = 7.5 Hz, 1H), 7.20 (s, 1H), 4.79-4.53 (m, 1H), 2.06 -1.88 (m, 2H), 1.71-1.57 (m, 4H), 1.30-1.19 (m, 2H), 0.89 (t, J = 8.0 Hz, 3H), 0.78 (t, J = 8.0 Hz, 3H).





1-37
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.04 (d, J = 2.0 Hz, 1H), 7.82 (dd, 7 = 7.5, 2.0 Hz, 1H), 7.20 (s, 1H), 7.15 (d, J = 7.5 Hz, 1H), 4.27-4.19 (m, 2H), 4.04 (s, 3H), 1.85- 1.75 (m, 2H), 1.79-1.71 (m, 1H), 1.65- 1.51 (m, 2H), 1.40-1.20 (m, 2H), 1.18-1.05 (m,2H), 0.89 (t, J = 8.0 Hz, 3H), 0.83 (t, J = 8.0 Hz, 3H).





1-38
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.38 (d, J = 7.5 Hz, 1H), 7.23- 7.16 (m,2H), 4.23 (t, J = 7.5 Hz, 2H), 1.72-1.61 (m, 2H), 1.47- 1.28 (m, 8H), 0.93 (t, J = 8.0 Hz, 3H).





1-39
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.41-7.34 (m, 2H), 7.21- 7.03 (m, 3H), 4.23 (t, J = 7.5 Hz, 2H), 1.72-1.35 (m, 12H), 0.93 (t, J = 8.0 Hz, 3H).





1-40
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.69 (d, J = 7.5 Hz, 2H), 7.57- 7.31 (d, J = 7.5 Hz, 2H), 7.10 (s, 1H), 4.23 (t, J = 7.5 Hz, 1H), 1.72-1.35 (m, 12H), 0.93 (t, J = 8.0 Hz, 3H).





1-41
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.49 (d, J = 7.5 Hz, 2H), 7.09 (d, J = 7.5 Hz, 2H), 7.02 (s, 1H), 4.23 (t, J = 7.5 Hz, 1H), 4.00 (t, J = 7.5 Hz, 1H), 1.73- 1.49 (m, 4H), 1.35-1.04 (m, 16H), 0.93-0.85 (m, 6H).





1-42
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.47-7.35 (m, 2H), 7.23- 7.11 (m, 2H), 2.91 (q, J = 7.0 Hz, 2H), 1.26 (t, J = 7.0 Hz, 3H).





1-43
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.48-7.40 (m, 2H), 7.21 (s, 1H), 7.11-7.03 (m, 2H), 2.85 (t, J = 8.0 Hz, 2H), 1.66-1.50 (m, 2H), 0.90 (t, J = 8.0 Hz, 3H).





1-44
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.57-7.51 (m, 2H), 7.38- 7.30 (m, 3H), 7.17-7.08 (m, 3H), 7.02-6.96 (m, 2H), 3.29 (hept, J = 6.5 Hz, 1H), 1.46 (d, J = 6.5 Hz, 6H).





1-45
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.49 (d, J = 7.5 Hz, 2H), 7.38 (d, J = 7.5 Hz, 2H), 7.33 (s, 1H), 2.85 (t, J = 8.0 Hz, 2H), 2.55-2.42 (m, 1H), 2.15- 2.07 (m, 2H), 1.82-1.70 (m, 6H), 1.43- 1.38 (m, 4H), 1.37 -1.26(m, 2H), 0.87 (t, J = 8.0 Hz, 3H).





1-46
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.31 (s, 1H), 7.13-6.97 (m, 2H), 6.76-6.67 (m, 2H), 4.13 (s, 2H), 3.26-3.18 (m, 1H), 1.73-1.60 (m, 2H), 1.36 (d, J = 6.5 Hz, 3H), 0.90 (t, J = 8.0 Hz, 3H).





1-47
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.52-7.43 (m, 3H), 7.29 (s, 1H), 1.26 (s, 9H).





1-48
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.52 (d, J = 2.0 Hz, 1H), 7.45 (d, J = 7.5 Hz, 1H), 7.35-7.27 (m, 2H), 2.85 (t, J = 7.5 Hz, 2H), 1.56- 1.23 (m, 6H), 0.94 (t, J = 8.0 Hz, 3H).





1-49
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.42-7.37 (m, 1H), 7.23- 7.14 (m, 3H), 2.85 (t, J = 8.0 Hz, 2H), 2.50 (s, 3H), 2.40 (s, 3H), 1.68-1.47 (m,3H), 0.88 (d, J = 6.5 Hz, 6H).





1-50
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.55 (d, J = 7.5 Hz, 2H), 7.41 (d, J = 7.5 Hz, 2H), 7.17 (s, 1H), 2.45 (s, 3H), 1.88 (q, J = 8.0 Hz, 1H), 1.24 (s, 6H), 0.85 (t, J = 8.0 Hz, 3H).





1-51
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.81-7.61 (m, 1H), 7.49- 7.28 (m, 2H), 7.22 (s, 1H), 2.73 (s, 2H), 0.95 (s, 9H).





1-52
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.41 (s, 2H), 7.23 (s, 1H), 3.97 (s, 3H), 2.85 (t, J = 8.0 Hz, 2H), 1.94-1.78 (m, 2H), 1.37 -1.24(m, 6H), 0.93 (t, J = 8.0 Hz, 3H).





1-53
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.67 (d, J = 2.0 Hz, 1H), 7.34- 7.23 (m, 2H), 7.21 (s, 1H), 2.85 (t, J = 8.0 Hz, 2H), 1.94- 1.80 (m, 2H), 1.38-1.22 (m, 8H), 0.93 (t, J = 8.0 Hz, 3H).





1-54
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.48-7.32 (m, 2H), 7.11- 6.93 (m, 3H), 2.85 (t, J = 8.0 Hz, 2H), 1.94-1.81 (m, 2H), 1.37- 1.20 (m, 10H), 0.94 (t, J = 8.0 Hz, 3H).





1-55
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.26 (s, 1H), 7.21-7.11 (m, 3H), 2.85 (t, J = 8.0 Hz, 2H), 1.94-1.81 (m, 2H), 1.38- 1.20 (m, 10H), 0.93 (t, J = 8.0 Hz, 3H).





1-56
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.47 (d, J = 7.5 Hz, 2H), 7.23 (d, J = 7.5 Hz, 2H), 2.85 (t, J = 8.0 Hz, 2H), 2.33 (s, 3H), 1.94 -1.81 (m, 2H), 1.38-1.20 (m, 14H), 0.93 (t, J = 8.0 Hz, 3H).





1-57
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.61 (d, J = 7.5 Hz, 2H), 7.41 (d, J = 7.5 Hz, 2H), 7.11 (s, 1H), 3.11 (s, 3H), 2.85 (t, J = 8.0 Hz, 1H), 1.94-1.81 (m, 2H), 1.47-1.20 (m, 18H), 0.92 (t, J = 8.0 Hz, 3H).





1-58
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.57-7.50 (m, 2H), 7.46- 7.37 (m, 3H), 7.32 (s, 1H), 2.93-2.81 (m, 1H), 1.79- 1.62 (m, 4H), 1.42-1.15 (m, 6H).





1-59
CF3


embedded image




embedded image








1-60
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.37-7.21 (m, 2H), 7.18 (s, 1H), 7.13-7.01 (m, 1H), 3.14 (s, 3H), 3.04 (s, 3H).





1-61
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.60 (d, J = 7.5 Hz, 2H), 7.53 (d, J = 7.5 Hz, 2H), 7.15 (s, 1H), 3.48 (q, 7 = 8.0 Hz, 4H), 1.23 (t, J = 8.0 Hz, 6H).





1-62
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.33-7.21 (m, 1H), 7.17- 7.04 (m, 2H), 3.58 (s, 3H), 3.44 (s, 3H).





1-63
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.42-7.34 (m, 2H), 7.16 (s, 1H), 7.11-7.03 (m, 2H), 3.57 (q, J = 8.0 Hz, 2H), 3.44 (s, 3H), 1.21 (t, J = 8.0 Hz, 3H).





1-64
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.46-7.38 (m, 2H), 7.17 (s, 1H), 7.11-7.03 (m, 2H), 3.47 -3.30 (m,4H), 3.19-3.04 (m, 4H), 2.32 (s, 3H).





1-65
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.53-7.45 (m, 2H), 7.41- 7.22 (m, 3H),7.16(s, 1H), 3.64-3.49 (m, 4H), 3.47- 3.32 (m, 4H).





1-66
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.38-7.24 (m, 1H), 7.23- 7.13 (m, 3H), 3.84-3.66 (m, 4H), 3.47-3.33 (m, 4H).





1-67
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.44-7.37 (m, 2H), 7.17 (s, 1H), 7.11-7.03 (m, 2H), 3.90 -3.77 (m,4H), 1.79- 1.65 (m, 6H).





1-68
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.57-7.43 (m, 2H), 7.46- 7.37 (m, 2H), 7.32 (s, 1H), 3.84-3.66 (m, 4H), 3.47- 3.33 (m, 4H)





1-69
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.52-7.44 (m, 2H), 7.18 (s, 1H), 7.11-7.03 (m, 2H), 3.46 -3.23 (m, 2H), 2.16 v 2.02 (m, 2H), 1.92-1.77 (m, 4H).





1-70
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.51-7.44 (m, 2H), 7.27 (s, 1H), 7.11-7.03 (m, 2H), 3.64 (s, 3H), 2.34-2.22 (m, 4H), 1.77-1.67 (m, 2H), 1.65- 1.55 (m, 2H).





1-71
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.43-7.28 (m, 2H), 7.23- 7.16 (m, 1H), 7.14 (s, 1H), 4.31 (s, 2H), 3.30 (s, 3H).





1-72
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.57-7.41 (m, 2H), 4.07 (q, J = 8.0 Hz, 1H), 2.34 (t, J = 7.5 Hz, 2H), 2.05 (d, J = 8.0 Hz, 2H), 1.17-1.05 (m, 2H).





1-73
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.68 (d, J = 7.5 Hz, 2H), 7.57 (d, J = 7.5 Hz, 2H), 7.22 (s, 1H), 4.22 (q, J = 8.0 Hz, 2H), 1.31 (t, J = 8.0 Hz, 3H).





1-74
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.53-7.48 (m, 1H), 7.47- 7.40 (m, 2H), 7.31-7.18 (m, 2H), 4.23 (s, 2H), 2.71 (d, J = 8.0 Hz, 2H), 2.02 (s, 3H), 1.21 (t, J = 8.0 Hz, 3H), 1.19 (s, 6H).





1-75
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.48-7.40 (m, 1H), 7.32- 7.21 (m, 3H), 7.03-6.90 (m, 1H), 4.79-4.66 (m, 1H), 4.06 (q, J = 8.0 Hz, 2H), 1.21 (t, J = 8.0 Hz, 3H).





1-76
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.48-7.40 (m, 2H), 7.20 (s, 1H), 7.11-7.03 (m, 2H), 3.39 (s, 2H), 2.05 (s, 3H).





1-77
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.40-7.29 (2, 1H), 7.23-7.10 (m, 2H), 2.71 (t, J = 8.0 Hz, 2H), 2.60 (t, J = 8.0 Hz, 2H), 2.14 (s, 3H).





1-78
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.42-7.34 (m, 2H), 7.16 (s, 1H), 7.11-7.03 (m, 2H), 3.46 -3.30 (m, 2H), 2.73-2,66 (m, 2H), 2.19-2.09 (m, 1H), 1.79 (s, 2H), 1.26 (s, 3H).





1-79
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.16-8.09 (m, 2H), 7.67- 7.55 (m, 3H), 7.37-7.18 (m, 2H), 7.14-7.00 (m, 3H).





1-80
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.49-7.35 (m, 4H), 7.36- 7.26 (m, 2H), 7.26-7.18 (m, 3H), 2.52 (s, 3H), 2.33 (s, 3H).





1-81
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.05-7.99 (m, 2H), 7.51- 7.41 (m, 3H), 7.24 (s, 1H), 7.21-7.13 (m, 2H), 2.50 (s, 3H), 2.41 (s, 3H), 2.30 (s, 3H).





1-82
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.05-7.89 (m, 4H), 7.76- 7.59 (m, 4H), 7.25 (s, 1H).





1-83
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.59-7.52 (m, 2H), 7.49- 7.40 (m, 5H), 7.33 (s, 1H), 7.32-7.28 (m, 1H).





1-84
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.12-8.06 (m, 2H), 7.37- 7.19 (m, 3H), 7.15-7.03 (m, 3H), 3.80 (s, 3H).





1-85
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.93-7.58 (m, 2H), 7.46- 7.39 (m, 2H), 7.23 (s, 1H),7.11 -7.03 (m, 4H),5.19(s, 1H).





1-86
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.90 (dd, J = 7.5, 2.0 Hz, 1H), 7.81-7.73 (m, 2H), 7.75- 7.68 (m, 1H), 7.44 (s, 1H), 7.39-7.16(m, 3H).





1-87
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.10 (dd, J = 7.5, 2.0 Hz, 1H), 7.60-7.43 (m, 3H), 7.46- 7.37 (m, 3H), 7.25-7.15 (m, 2H), 2.39 (s, 3H).





1-88
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.83-7.68 (m, 2H), 7.52- 7.33 (m, 4H), 7.27-7.21 (m, 3H).





1-89
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.96-7.89 (m, 2H), 7.85- 7.79 (m, 2H), 7.73 (s, 1H), 7.46-7.38 (m, 2H), 7.33- 7.26 (m, 2H), 7.22 (s, 1H), 2.71 (q, J = 8.0 Hz, 2H), 2.10 (s, 3H), 1.21 (t, J = 8.0 Hz, 3H).





1-90
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.71-7.65 (m, 2H), 7.48- 7.34 (m, 2H), 7.25-7.20 (m, 3H), 6.82-6.75 (m, 2H), 3.02 (s, 6H).





1-91
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.57 (d, J = 2.0 Hz, 1H), 7.50- 7.36 (m, 4H), 7.33 (s, 1H),7.11 -7.03 (m, 2H).





1-92
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.24 (d, J = 2.0 Hz, 1H), 7.73 (dd, J = 7.5, 2.0 Hz, 1H), 7.54 (d, J = 7.5 Hz, 1H), 7.52 (d, J = 7.5 Hz, 2H), 7.25 (s, 1H), 7.13 (d, J = 7.5 Hz, 2H), 2.77 (d, J = 8.0 Hz, 2H), 1.19 (t, J = 8.0 Hz, 3H).





1-93
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.53-7.45 (m, 2H), 7.41- 7.32 (m, 2H), 7.25 (s, 1H), 7.15-7.03 (m, 2H).





1-94
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.31-7.27 (m, 3H), 7.31- 7.24 (m, 1H), 7.27-7.18 (m, 3H), 7.17-7.08 (m, 2H), 3.92 (s, 2H).





1-95
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.53-7.46 (m, 3H), 7.43- 7.31 (m, 3H), 7.25-7.15 (m, 3H), 3.54 (s, 2H).





1-96
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.59-7.41 (m, 5H), 7.39- 7.27 (m, 5H), 7.16 (s, 1H), 5.90 (d, J = 10.5 Hz, 1H).





1-97
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.50-7.42 (m, 4H), 7.45- 7.35 (m, 5H), 7.11-7.00 (d, J = 11.0 Hz, 1H),5.87 (d, J = 11.0 Hz, 1H).





1-98
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.62-7.55 (m, 2H), 7.47- 7.38 (m, 4H), 7.34 (s, 1H), 7.11 -7.03 (m, 2H),5.99 (s, 2H).





1-99
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.40-7.30 (m, 3H), 7.29- 7.18 (m, 3H), 7.21 (s, 1H), 6.99-6.87 (m, 3H), 3.10 (t, J = 8.0 Hz, 2H), 3.00 (t, J = 8.0 Hz, 2H).





1-100
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.48-7.40 (m, 3H), 7.24- 7.16 (m, 3H), 7.11-7.03 (m, 3H), 5.69 (s, 2H), 5.56 (s, 2H).





1-101
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.51-7.38 (m, 3H), 7.25- 7.14 (m, 3H),7.17(s, 1H), 7.08-7.00 (m, 2H), 4.52 (s, 2H), 4.31 (s, 3H).





1-102
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.49-7.41 (m, 3H), 7.21 (s, 1H), 7.11-7.03 (m, 2H), 6.89 -6.81 (m, 4H).





1-103
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.58-7.46 (m, 3H), 7.32- 7.20 (m, 5H), 7.19-7.07 (m, 2H), 3.70 (t, J = 8.0 Hz, 2H), 2.90 (t, J = 8.0 Hz, 2H), 2.70 (s, 3H).





1-104
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.57-7.51 (m, 2H), 7.52- 7.45 (m, 2H), 7.33 (s, 1H), 7.27 (s, 1H), 7.28-7.16 (m, 1H).





1-105
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.55 (dd, J = 7.5, 1.5 Hz, 1H), 7.42-7.33 (m, 3H), 7.24 (s, 1H), 7.28-7.16 (m, 3H), 6.48 (t, J = 7.5 Hz, 1H), 3.68 (s, 3H).





1-106
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.63 (d, J = 7.5 Hz, 2H), 7.41- 7.34 (m, 2H), 7.24 (s, 1H), 7.15-7.02 (m, 2H), 6.47- 6.38 (m, 1H).





1-107
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.11-8.06 (m, 1H), 7.57- 7.50 (m, 2H), 7.33-7.27 (m, 1H), 7.25 (s, 1H), 2.62 (s, 3H).





1-108
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.42-7.28 (m, 2H), 7.24 (s, 1H), 7.20-7.09 (m, 1H), 6.58 (s, 1H), 2.42 (s, 3H).





1-109
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.19-8.07 (m, 1H), 7.43- 7.27 (m, 3H), 7.24 (s, 1H), 7.20-7.06 (m, 2H).





1-110
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.37 (d, J = 2.5 Hz, 1H), 7.36- 7.28 (m, 2H), 7.22 (s, 1H),7.11 -7.03 (m, 2H), 6.80 (d, J = 7.5 Hz, 1H).





1-111
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.75 (d, J = 1.3 Hz, 1H), 7.70 (d, J = 8.0 Hz, 2H), 7.38 (d, J = 8.0 Hz, 2H).





1-112
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 9.21 (s, 1H), 8.79 (d, J = 5.5 Hz, 1H), 8.73 (d, J = 5.5 Hz, 1H), 7.24-7.13 (m, 4H).





1-113
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.56 (dd, J = 5.0, 1.0 Hz, 1H), 7.80 (dd, J = 8.0, 1.0 Hz, 1H), 7.37 (dd, J = 8.0, 5.0 Hz, 1H), 7.30-7.23 (m, 2H), 7.18- 7.13 (m, 2H), 2.97 (q, J = 8.0 Hz, 2H), 1.39 (t, J = 8.0 Hz, 3H)





1-114
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.12-8.02 (m, 2H), 8.08- 7.99 (m, 2H), 8.00-7.94 (m, 1H), 7.73-7.64 (m, 2H), 7.49 -7.41 (m, 2H),7.26 (s, 1H), 7.11-7.03 (m, 2H)





1-115
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.66-8.59 (m, 2H), 7.97 (dd, J = 7.5, 1.5 Hz, 1H), 7.62 (d, J = 7.5 Hz, 1H), 7.46-7.40 (m, 1H), 7.32-7.25 (m,2H), 7.26 -7.15 (m, 2H), 6.66-6.52 (m, 1H).





1-116
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.33-8.05 (m, 3H), 7.92 (d, J = 7.5, 1.5 Hz, 1H), 7.77-7.67 (m, 2H), 7.54-7.48 (m, 2H), 7.45-7.39 (m, 2H), 7.27 (s, 1H).





1-117
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.23-8.04 (m, 2H), 7.92 (d, J = 7.5 Hz, 1H), 7.75 (d, J = 7.5 Hz, 1H), 7.56-7.48 (m, 2H), 7.41-7.30 (m, 3H), 7.25 (s, 1H), 6.86 (dd, J = 7.5, 1.5 Hz, 1H).





1-118
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.77 (dd, J = 7.0, 2.5 Hz, 1H), 7.72 (d, J = 7.5 Hz, 2H), 7.62- 7.56 (m, 2H), 7.24 (s, 1H), 7.19-7.10 (m, 2H), 5.99 (s, 2H).





1-119
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.11-8.02 (m,2H), 7.59- 7.41 (m, 1H), 7.50-7.40 (m, 3H), 7.36-7.30 (m, 2H), 7.11 -7.03 (m, 2H).





1-120
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.65-7.58 (m, 2H), 7.54 (d, J = 1.5 Hz, 1H), 7.44-7.33 (m, 2H), 7.32-7.24 (m, 1H), 7.28 (s, 1H), 7.26-7.15 (m, 2H).





1-121
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.62 (s, 1H), 7.51-7.44 (m, 2H), 7.11-7.03 (m, 2H), 3.07 (q, J = 8.0 Hz, 2H), 1.50 (t, J = 8.0 Hz, 3H).





1-122
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.77 (d, J = 7.5 Hz, 2H), 7.57- 7.50 (m, 3H), 1.72-1.61 (m, 1H), 0.81-0.73 (m, 2H), 0.58 -0.51 (m,2H).





1-123
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.66-7.52 (m, 2H), 7.46- 7.39 (m, 2H), 7.34-7.29 (m, 1H), 5.15 (s, 2H), 3.05 (s, 3H), 2.71 (d, J = 8.0 Hz,2H), 1.21 (t, J = 8.0 Hz, 3H).





1-124
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.63-7.59 (m, 2H), 7.45- 7.33 (m, 2H), 7.25-7.18 (m, 1H), 4.45 (s, lH),3.75 (t, J = 7.5 Hz, 2H), 2.63 (t, J = 7.5 Hz, 2H), 1.83- 1.68 (m, 2H).





1-125
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.57 (s, 1H), 7.45-7.37 (m, 2H), 7.11-7.03 (m, 2H), 2.50 -2.38 (m, 8H), 2.27 (s, 3H).





1-126
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.76-7.70(m, 2H), 7.61 (s, 1H), 7.49-7.43 (m, 2H), 7.41 -7.30 (m, 1H), 7.20-7.10 (m, 2H), 2.42 (s, 3H).





1-127
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.78 (d, J = 7.5 Hz, 2H), 7.64 (s, 1H), 7.56-7.41 (m, 1H), 7.51-7.42 (m,2H), 7.19- 7.10 (m, 2H).





1-128
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.78-7.64 (m, 2H), 7.56- 7.41 (m, 1H), 7.51-7.42 (m, 2H), 7.19-7.10 (m,2H).





1-129
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.86 (d, J = 7.5 Hz, 2H), 7.76 (d, J = 7.5 Hz, 2H), 7.59 (s, 1H), 7.42-7.34 (m, 1H),7.16 -7.07 (m, 2H).





1-130
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.91 (d, J = 7.5 Hz, 2H), 7.78 (d, J = 7.5 Hz, 2H), 7.59 (s, 1H), 7.45-7.38 (m, 1H), 7.26 -7.17 (m, 2H).





1-131
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.70 (s, 1H), 7.64-7.57 (m, 2H), 7.41-7.31 (m, 3H), 7.08 (s, 2H), 2.55 (s, 6H), 2.13 (s, 3H).





1-132
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.76-7.70 (m, 2H), 7.58 (s, 1H), 7.45 (ddd, J = 7.6, 6.2, 2.1 Hz, 4H), 7.11-7.03 (m, 2H), 2.42 (d, J = 1.5 Hz, 2H).





1-133
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.83 (d, J = 2.0 Hz, 1H), 7.71- 7.63 (m, 2H), 7.55-7.47 (m, 3H), 7.11-7.03 (m, 2H).





1-134
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.84-7.76 (m, 2H), 7.59 (s, 1H), 7.49-7.41 (m, 2H),7.33 -7.24 (m, 2H), 7.11-7.03 (m, 2H).





1-135
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.46(d, J = 7.5Hz, 2H), 8.07 (d, J = 7.5 Hz, 2H), 7.58 (s, 1H), 7.32-7.22 (m, 3H).





1-136
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.32 (s, 1H), 8.08 (s, 1H), 7.60 -7.50 (m, 3H), 7.41-7.30 (m, 3H).





1-137
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.17-8.11 (m, 2H), 8.12- 8.05 (m, 2H), 7.53 (s, 1H), 7.46-7.38 (m,2H), 7.11- 7.03 (m, 2H), 3.30 (s, 3H).





1-138
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.61 (s, 1H), 7.64-7.57 (m, 1H), 7.52-7.39 (m, 2H), 7.28 -7.17 (m, 2H).





1-139
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.60-7.50 (m, 3H), 7.43 (d, J = 7.5 Hz, 2H), 7.40 (dd, J = 2.5, 1.5 Hz, 1H), 7.32-7.26 (m, 2H), 7.18 (s, 1H), 7.43 (t, J = 73.5 Hz, 1H).





1-140
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.33-8.28 (m, 2H), 8.17- 8.06 (m, 1H), 7.73-6.65 (m, 1H), 7.60-7.51 (m, 3H), 7.41 -7.30 (m, 3H), 2.60 (s, 3H).





1-141
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.10 (d, J = 7.5 Hz, 2H), 8.04 (d, J = 7.5 Hz, 2H), 7.69 (d, J = 7.5 Hz, 2H), 7.57 (d, J = 7.5 Hz, 2H), 7.17 (s, 1H), 6.41 (s, 2H).





1-142
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.79-7.70 (m, 3H), 7.45- 7.38 (m, 2H), 7.31-7.19 (m, 3H), 7.18-7.12 (m, 2H), 7.12 -7.04 (m, 2H).





1-143
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.60 (s, 1H), 7.53-7.45 (m, 2H), 7.30-7.20 (m, 5H), 7.11 -7.03 (m, 2H), 4.29 (s, 2H).





1-144
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.80 (dd, J = 7.5, 1.5 Hz, 1H), 8.26-8.15 (m, 2H), 8.01- 7.78 (m, 2H), 7.58-7.50 (m, 4H), 7.51-7.40 (m, 3H).





1-145
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.16 (d, J = 2.5 Hz, 1H), 7.75- 7.69 (m, 2H), 7.47-7.36 (m, 3H), 7.33-7.24 (m, 1H), 2.71 -2.61 (d, J = 8.0 Hz, 2H), 1.21 (t, J = 8.0 Hz, 3H).





1-146
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.41 (d, J = 1.5 Hz, 1H),7.99 (dd, J = 8.0, 1.5 Hz, 1H), 7.63 (s, 1H), 7.50-7.39 (m, 4H), 7.32-7.21 (m, 2H), 7.18- 7.08 (m, 3H), 6.96(dd, J = 7.5, 2.0 Hz, 1H).





1-147
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 9.38 (s, 1H), 8.81 (d, J = 1.5 Hz, 1H), 7.99-7.91 (m, 2H), 7.63 (s, 1H), 7.48-7.25 (m, 3H).





1-148
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.43 (d, J = 1.5 Hz, 1H), 8.15 (dd, J = 2.5,1.5 Hz, 1H), 7.85 (dd, J = 7.5,1.5 Hz, 1H), 7.77 -7.60 (m, 3H), 7.56-7.49 (m, 3H).





1-149
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.97 (dd, J = 6.5, 2.0 Hz, 1H), 7.70-7.65 (m, 2H), 7.61 (d, J = 1.5 Hz, 1H), 7.53-7.43 (m, 3H), 7.37-7.27 (m, 3H), 2.71 -2.62 (d, J = 8.0 Hz, 2H), 1.21 (t, J = 8.0 Hz, 3H).





1-150
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.73 (s, 1H), 7.59-7.49 (m, 2H), 7.36 (d, J = 2.5 Hz, 1H), 7.31-7.25 (m, 3H), 3.66 (s, 3H).





1-151
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.73-7.65 (m, 2H), 7.62 (s, 1H), 7.57-7.42 (m, 2H), 7.25 -7.19 (m,2H), 3.92 (s, 3H).





1-152
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.93-7.85 (m, 2H), 7.80 (dd, J = 7.5, 1.5 Hz, 1H), 7.72 (s, lH),7.33-7.19(m, 3H),7.11 (d, J = 7.5 Hz, 1H), 6.50 (dd, J = 7.5, 1.5 Hz, 1H), 3.80 (s, 3H).





1-153
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.76-7.60 (m, 4H), 7.56- 7.44 (m, 4H), 7.26-7.14 (m, 2H), 2.66 (q, J = 8.0 Hz, 1H), 1.21 (t, J = 8.0 Hz, 1H).





1-154
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.45 (dd, J = 7.5, 5.5 Hz, 2H), 7.28 (s, 1H),7.07(dd, J = 9.0, 7.5 Hz, 2H), 1.41 (t, J = 8.0 Hz, 2H), 1.36-1.22 (m, 12H), 0.93 (t, J = 8.0 Hz, 3H).





1-155
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.44 (d, J = 7.5 Hz, 2H), 7.22- 7.13 (m,3H), 3.62 (q,7 = 8.0 Hz, 2H), 2.33 (s, 3H), 1.36 (t, J = 8.0 Hz, 3H).





1-156
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.50(d, J = 7.5 Hz, 2H), 7.21 (s, 1H), 6.80 (d, J = 7.5 Hz, 2H), 3.80 (s, 3H),3.60(t, J = 7.5 Hz, 2H), 1.78-1.66 (m, 2H), 1.01 (t, J = 8.0 Hz, 3H).





1-157
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.30-7.22 (m, 2H), 7.20 (s, 1H), 7.15-7.05 (m, 1H), 3.65 (t, J = 8.0 Hz, 2H), 1.46-1.36 (m, 4H), 1.03 (t, J = 8.0 Hz, 3H).





1-158
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.52-7.43 (m, 2H), 7.34 (s, 1H), 7.27 (dd, J = 7.5, 2.0 Hz, 1H), 3.45 (d, J = 7.0 Hz, 2H), 1.49-1.38 (m, 1H), 0.92 (d, J = 7.5 Hz, 6H).





1-159
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.84 (dd, J = 2.0 Hz, 1H), 7.62 (d, J = 7.5 Hz, 1H), 7.43-7.33 (m, 1H), 7.19 (s, 1H), 3.60 (t, J = 7.5 Hz, 2H), 2.50 (s, 3H), 1.67-1.60 (m, 1H), 1.43- 1.31 (m, 2H), 0.97 (d, J = 6.5 Hz, 6H).





1-160
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.31 (d, J = 7.5 Hz, 1H), 7.22 (s, 1H), 7.14 (d, J = 7.5 Hz, 1H), 3.60 (t, J = 7.0 Hz, 2H), 1.65-1.55 (m, 2H), 1.43- 1.31 (m, 6H), 0.89 (t, J = 7.5 Hz, 3H).





1-161
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.40-7.35 (m, 2H), 7.33- 7.15 (m, 3H), 3.88-3.73 (m, 1H), 2.65-2.55 (m, 2H), 1.69 -1.55 (m, 2H), 1.59-1.39 (m, 3H), 1.28-1.07 (m, 11H), 0.89 (t, J = 7.5 Hz, 3H).





1-162
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.45-7.37(m, 2H), 7.20 (s, 1H), 7.11-7.03 (m, 2H), 3.65 (q, J = 8.0 Hz, 4H), 1.17 (t, J = 8.0 Hz, 6H).





1-163
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.45-7.37 (m, 2H), 7.24- 7.11 (m, 2H), 2.85 (t, J = 8.0 Hz, 2H), 1.94-1.81 (m, 2H), 1.38-1.29 (m, 2H), 1.32- 1.20 (m, 8H), 0.93-0.85 (t, J = 8.0 Hz, 3H).





1-164
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.53-7.47 (m, 2H), 7.48- 7.40 (m, 2H), 7.28-7.20 (m, 3H), 7.11-7.03 (m, 3H).





1-165
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.40-7.28 (m, 2H), 7.19- 7.14 (m, 2H), 2.61 (q, J = 8.0 Hz, 2H), 1.35 (t, J = 8.0 Hz, 3H).





1-166
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.45-7.37(m, 2H), 7.28 (s, 1H), 7.11-7.03 (m, 2H).





1-167
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.58 (dd, J = 5.5, 2.0 Hz, 1H), 7.36-7.29 (m, 1H), 7.32 (s, lH),7.16(dd, J = 10.5, 7.5 Hz, 1H), 3.78 (s, 6H).





1-168
CF3


embedded image




embedded image








1-169
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.38-7.30 (m, 1H), 7.25- 7.13 (m, 2H), 7.08 (s, 1H), 2.65 (s, 6H).





1-170
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.46 (d, J = 7.0 Hz, 2H), 7.20 (d, J = 7.0 Hz,2H),7.15(s, 1H), 2.59 (s, 3H), 2.33 (s, 3H), 2.17 (q, J = 8.0 Hz, 2H), 0.92 (t, J = 8.0 Hz, 3H).





1-171
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.49 (d, J = 7.5 Hz, 2H), 6.80- 6.74 (m, 3H), 3.80 (s, 3H), 2.58 (s, 3H), 2.11 (t, J = 7.5 Hz, 2H), 1.54-1.44 (m, 2H), 0.76 (t, J = 8.0 Hz, 3H).





1-172
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.47-7.40 (m, 2H), 7.15 (s, 1H), 7.11-7.03 (m, 2H), 6.87 (t, J = 7.0 Hz, 1H), 2.11-2.00 (m, 2H), 1.54-1.42 (m, 2H), 0.81 (t, J = 8.0 Hz, 3H).





1-173
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.95-7.89 (m, 2H), 7.72- 7.66 (m, 2H), 7.09 (s, 1H), 2.62 (s, 3H), 2.05 (d, J = 7.0 Hz, 2H), 1.77- 1.68 (m, 1H), 0.97 (d, J = 6.5 Hz, 6H).





1-174
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.41 (d, J = 2.0 Hz, 1H), 7.32 (dd, J = 7.5, 2.0 Hz, 1H), 7.15 (d, J = 7.5 Hz, 1H), 7.08 (s, 1H), 2.66 (s, 3H), 2.30 (s, 3H), 2.20 (s, 3H), 1.16 (s, 9H).





1-175
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.99 (d, J = 7.0 Hz, 2H), 7.87- 7.81 (m, 3H), 3.30 (s, 3H), 2.59 (s, 3H), 2.11 (t, J = 8.0 Hz, 2H), 1.55- 1.40 (m, 4H), 0.95 (t, J = 8.0 Hz, 3H).





1-176
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.54 (d, J = 2.0 Hz, 1H), 7.49 (d, J = 7.5 Hz, 1H), 7.34 (dd, J = 7.5, 2.0 Hz, 1H), 7.14 (s, 1H), 2.57 (s, 3H), 2.11 (t, J = 8.0 Hz, 2H), 1.55-1.47 (m, 2H), 1.34-1.23 (m, 6H), 0.93 (t, J = 8.0 Hz, 3H).





1-177
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.50 (d, J = 7.5 Hz, 2H), 7.19- 7.03 (m, 3H), 4.00 (t, J = 7.5 Hz, 2H), 2.21-2.07 (m, 4H), 1.60-1.44 (m, 8H), 1.36- 1.23 (m,5H), 1.04 (t, J = 8.0 Hz, 3H), 0.92 (t, J = 8.0 Hz, 3H).





1-178
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.43-8.25 (m, 2H), 7.91- 7.80 (m, 1H), 7.63-7.55 (m, 1H), 7.16 (s, 1H), 2.11 (t, J = 7.5 Hz, 4H), 1.55-1.40 (m, 8H), 0.95 (t, J = 8.0 Hz, 6H).





1-179
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.62 (d, J = 2.5 Hz, 1H), 7.30 (s, 1H), 6.45 (d, J = 2.5 Hz, 1H), 4.00 (s, 3H), 2.55-2.41 (m, 2H), 2.32-2.02 (m, 2H), 1.68- 1.57 (m, 1H), 1.37- 1.19 (m, 2H), 1.02-0.88 (m, 9H).





1-180
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.47 (d, J = 7.0 Hz, 2H), 7.17- 7.03 (m, 3H), 2.05 (d, J = 7.0 Hz, 4H), 1.72-1.60 (m, 2H), 0.96 (d, J = 6.5 Hz, 12H).





1-181
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.59-7.51 (m, 2H), 7.41- 7.33 (m, 3H), 7.16 (s, 1H), 2.59 (s, 3H), 2.40 (t, J = 7.5 Hz, 2H), 1.61-1.55 (m, 3H), 1.31-1.15 (m, 2H), 1.17- 1.09 (m, 1H), 1.12-1.02 (m, 2H), 0.85 (t, J = 7.5 Hz, 2H), 0.74 (d, J = 6.5 Hz, 3H).





1-182
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.35-7.27 (m, 2H),7.16(dd, J = 7.5, 1.0 Hz, 1H), 7.13 (s, 1H), 2.57 (s, 3H), 2.30 (s, 3H), 2.20 (s, 3H), 2.11 (t, J = 8.0 Hz, 2H), 1.55-1.22 (m, 14H), 0.89 (t, J = 8.0 Hz, 3H).





1-183
CF3


embedded image




embedded image








1-184
CF3


embedded image




embedded image








1-185
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.47-7.40 (m, 2H), 7.16 (s, 1H), 7.11-7.03 (m, 2H), 4.21 (s, 2H), 3.19(s, 3H), 2.57 (s, 3H).





1-186
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.44-7.37 (m, 1H), 7.25- 7.16 (m, 2H),7.16(s, 1H), 3.28 (s, 2H), 2.60 (s, 3H), 2.00 (s, 3H).





1-187
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.59-7.51 (m, 2H), 7.41- 7.27 (m, 3H),7.14(s, 1H), 2.73 (q, J = 6.5 Hz, 1H), 2.59 (s, 3H), 2.10 (s,3H), 1.31 (d, J = 6.5 Hz, 3H).





1-188
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.45 (d, J = 7.5 Hz, 2H), 7.25 (d, J = 7.5 Hz, 2H), 7.11 (s, 1H), 2.73 (q, J = 6.5 Hz, 1H), 2.59 (s, 3H), 2.19 (d, J = 8.0 Hz, 2H), 1.31 (d, J = 6.5 Hz, 3H) 1.24 (t, J = 8.0 Hz, 3H).





1-189
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.01-7.91 (m, 2H), 7.70- 7.53 (m, 2H), 7.19 (s, 1H), 3.28 (s, 2H), 2.60 (s, 3H), 2.48 (q, J = 8.0 Hz, 2H), 1.21 (t, J = 8.0 Hz, 3H).





1-190
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.46 (d, J = 7.0 Hz, 1H), 7.17- 7.10 (m, 3H), 2.75-2.63 (m, 4H), 2.59 (s, 3H), 2.49 (q, J = 8.0 Hz, 2H), 1.21 (t, J = 8.0 Hz, 3H).





1-191
CF3


embedded image




embedded image








1-192
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.73 (d, J = 7.5 Hz, 1H), 7.60- 7.53 (m, 3H), 3.28 (s, 2H), 2.71 (t, J = 8.0 Hz, 1H), 2.58 (s, 3H), 1.38-1.20 (m, 12H), 0.93 (t, J = 8.0 Hz, 3H).





1-193
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.50-7.40 (m, 1H), 7.37- 7.28 (m, 2H), 7.22-7.17 (m, 1H), 7.11 (s, 1H), 2.71-2.62 (m, 4H), 2.17 (q, J = 8.0 Hz, 2H), 1.60-1.50 (m, 6H), 1.21 (t, J = 8.0 Hz, 3H).





1-194
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.53 (t, J = 7.0 Hz, 2H), 7.44 (t, J = 7.0 Hz, 2H), 7.15 (s, 1H), 2.66-2.53 (m, 4H), 2.50 -2.36 (m, 4H).





1-195
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.58-7.50 (m, 2H), 7.52- 7.39 (m, 4H), 7.33-7.26 (m, 2H),7.17(s, 1H), 7.11-7.03 (m, 2H).





1-196
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.50 (s, 5H), 7.53-7.40 (m, 1H), 7.28-7.19 (m, 2H), 7.15 (s, 1H), 3.08 (s, 3H).





1-197
CF3


embedded image




embedded image








1-198
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.59-8.37 (m, 2H), 7.72- 7.49 (m, 4H), 7.41-7.33 (m, 4H),7.19(s, 1H), 7.11-7.03 (m, 2H).





1-199
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.52-7.44 (m, 2H), 7.38- 7.23 (m, 7H), 7.26-7.16 (m, 4H), 7.09 (s, 1H).





1-200
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.62-7.52 (m, 2H), 7.45- 7.37 (m, 1H), 7.32-7.19 (m, 4H), 7.13 (s, 1H), 2.36 (s, 3H).





1-201
CF3


embedded image




embedded image








1-202
CF3
OEt


embedded image








1-203
CF3


embedded image




embedded image








1-204
CF3


embedded image




embedded image








1-205
CF3


embedded image




embedded image








1-206
CF3


embedded image




embedded image








1-207
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.50-7.43 (m, 2H), 7.35 (s, 1H), 7.11-7.03 (m, 2H), 4.07 (q, J = 8.0 Hz, 2H), 3.95 (t, J = 7.5 Hz, 2H), 2.48 (t, J = 7.0 Hz, 2H), 2.11-2.00 (m, 2H), 1.17 (t, J = 8.0 Hz, 3H).





1-208
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.45-7.32 (m, 3H), 7.26- 7.14 (m, 4H), 6.83-6.76 (m, 2H).





1-209
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.53-7.45 (m, 3H), 7.44- 7.27 (m, 3H), 7.11-7.03 (m, 4H), 4.98 (s, 2H).





1-210
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.44-7.27 (m, 4H), 7.13- 7.07 (m, 5H), 4.98 (s, 2H).





1-211
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.50-7.42 (m, 3H), 7.35 (s, 1H), 7.14-7.03 (m, 3H), 5.12 (s, 2H), 3.86 (s, 3H).





1-212
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.07-8.00 (m, 3H), 7.64- 7.56 (m, 3H), 7.54-7.42 (m, 2H),7.31 (s, 1H), 7.11-7.03 (m, 2H), 5.70 (s, 2H).





1-213
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 8.03-7.89 (m, 2H), 7.64- 7.56 (m, 2H), 7.54-7.34 (m, 1H), 7.28-7.18 (m, 3H), 5.70 (s, 2H).





1-214
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.42 (d, J = 7.0 Hz, 2H), 7.22 (d, J = 7.0 Hz, 2H), 7.12 (s, 1H), 2.47 (s, 6H), 2.33 (s, 3H).





1-215
CF3


embedded image




embedded image


(500 MHz, Chloroform-d) δ 7.47 (d, J = 7.5 Hz, 2H), 7.39 (d, J = 7.5 Hz, 2H), 7.12 (s, 1H), 2.59 (q, J = 8.0 Hz, 4H), 1.04 (t, J = 8.0 Hz, 6H).





1-216
CF


embedded image




embedded image








1-217
CF3


embedded image




embedded image








1-218
CH2F


embedded image




embedded image








1-219
CH2F


embedded image




embedded image








1-220
CH2F


embedded image




embedded image








1-221
CHF2


embedded image




embedded image








1-222
CHF2


embedded image




embedded image








1-223
CFCF3


embedded image




embedded image








1-224
CFCF3


embedded image




embedded image








1-225
CFCF3


embedded image




embedded image








1-226
CF3


embedded image




embedded image








1-227
CF3


embedded image




embedded image








1-228
CF3


embedded image




embedded image








1-229
CF3


embedded image




embedded image








1-230
CF3


embedded image




embedded image








1-231
CF3


embedded image




embedded image








1-232
CF3


embedded image




embedded image








1-233
CF3


embedded image




embedded image








1-234
CF3


embedded image




embedded image








1-235
CF3


embedded image




embedded image








1-236
CF3


embedded image




embedded image








1-237
CF3


embedded image




embedded image








1-238
CF3


embedded image




embedded image








1-239
CF3


embedded image




embedded image








1-240
CF3


embedded image




embedded image



1H NMR (500 MHz, Chloroform-d) 7.56-7.48 (m, 2H), 7.41-7.33 (m, 3H), 7.00- 6.91 (m, 2H), 5.27 (hept, J = 6.5 Hz, 1H), 1.73 (d, J = 7.0 Hz, 3H), 1.31 (d,J = 6.5 Hz, 6H).






1-241
CF3
CN


embedded image








1-242
CF3


embedded image




embedded image



1H NMR (500MHz, Chloroform-d) δ 7.77-7.66 (m, 4H), 7.60-7.53 (m, 2H), 7.41-7.22 (m, 3H).






1-243
CF3


embedded image




embedded image



1H NMR (500MHz, Chloroform-d) δ 7.51-7.44 (m, 2H), 7.42-7.33 (m, 4H), 7.20 (s, 1H), 7.07-7.00 (m, 3H).






1-244
CF3


embedded image




embedded image



1H NMR (500MHz, Chloroform-d) δ 7.59-7.51 (m, 2H), 7.41-7.33 (m, 2H), 7.15 (s, 1H), 2.59 (s, 3H), 2.51 (s, 3H), 2.30 (s, 3H).






1-245
CF3


embedded image




embedded image



1H NMR (500 MHz, Chloroform-d) δ 7.55-7.47 (m, 2H), 7.41-7.30 (m, 2H), 7.11 (s, 1H), 2.47 (s, 6H), 2.32 (s, 3H).






1-246
CF3


embedded image




embedded image



1H NMR (500 MHz, Chloroform-d) 7.58-7.42 (m, 3H), 7.31-7.12(m, 3H), 2.85 (t, J = 7.5 Hz, 2H), 1.38-1.26 (m, 12H), 0.89 (t, J = 7.0 Hz, 1H).






1-247
CF3


embedded image




embedded image



1H NMR (500 MHz, Chloroform-d) 7.65-7.49 (m, 6H), 7.42-7.27 (m, 4H), 7.11 (s, 1H), 4.98 (s, 2H).






1-248
CF3


embedded image




embedded image








1-249
CF3


embedded image




embedded image








1-250
CF3


embedded image




embedded image








1-251
CF3


embedded image


Me









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:


1. Synthesis of Compound 1




embedded image


(1) experimental apparatus: a 50 mL round bottom single-necked flask, a magnetic stirrer, and a thermostatic magnetic stirrer.


Compound II (1 g, 3.9 mmol), Compound 1-a (0.72 g, 5.9 mmol), and potassium carbonate (1.62 g, 11.7 mmol) were placed in the round bottom flask, added with 1,4-dioxane (10 mL)/water (2 mL) and then subjected to replacement of nitrogen gas three times, followed by the quickly addition of Pd(dppf)Cl2CH2Cl2 (0.16 g), and subjected to replacement of nitrogen gas three times, then the reaction solution was subjected to replacement of nitrogen gas three times once again, and finally the reaction was carried out at 100° C. for 36 hours. The reaction was complete detected by HPLC, the reaction system was concentrated, and separated by column chromatography to give 0.8 g (3.1 mmol, yield: 79%) of Compound 1-b (white solid).


(2) experimental apparatus: 50 mL round bottom single-necked flask, magnetic stirrer, thermostatic magnetic stirrer, and spherical condenser.


Compound 1-b (0.8 g, 3.1 mmol) was placed in the round bottom flask, 8 mL of water and sodium hydroxide (0.37 g, 9.3 mmol) were added, the resulting mixture was reacted at 80° C. for 12 h. After the reaction was completed, the reaction solution was extracted with 30 mL of dichloromethane three times. The aqueous phase was adjusted to pH 2 with 1N HCl solution, and a white solid was precipitated. The filter cake was obtained by filtration, and then dried to give 0.65 g (2.7 mmol, yield 87%) of Compound 1.


2. Synthesis of Compound 27




embedded image


(1) Compound II (1 g, 3.9 mmol), Compound 27-a (0.92 g, 5.9 mmol), and potassium carbonate (1.62 g, 11.7 mmol) were placed in a round bottom flask, added with 1,4-dioxane (10 mL)/water (2 mL) and then subjected to replacement of nitrogen gas three times, followed by the quickly addition of Pd(dppf) Cl2CH2Cl2 (0.16 g) and subjected to replacement of nitrogen gas three times, the reaction solution was then subjected to replacement of nitrogen gas three times once again, and finally the reaction was carried out at 120° C. for 36 hours. The reaction was complete detected by HPLC, the reaction system was concentrated and purified by concentration column chromatography (PE:EA=5:1) to give 0.71 g (2.4 mmol, yield 61%) of Compound 27-b (white solid).


(2) Compound 27-b (0.71 g, 2.4 mmol) was placed in a round bottom flask, 8 mL of water and sodium hydroxide (0.096 g, 2.4 mmol) were added, the resulting mixture was reacted at 120° C. for 12 h. The reaction was complete detected by TEC, then the reaction solution was cooled and extracted three times with 30 mL of dichloromethane. The aqueous phase was adjusted to pH=2 with 1N HCl solution, and a white solid was precipitated, which was filtered to give a filter cake, and dried to give 0.35 g (1.3 mmol, yield 87%) of Compound 27.


3. Synthesis of Compound 32




embedded image


(1) Compound II (1 g, 3.9 mmol), Compound 32-a (0.82 g, 5.9 mmol), and potassium carbonate (1.62 g, 11.7 mmol) were placed in a round bottom flask, added with 1,4-dioxane (10 mL)/water (1 mL) and then subjected to replacement of nitrogen gas three times, followed by the quickly addition of Pd(dppf)Cl2CH2Cl2 (0.16 g), and subjected to replacement of nitrogen gas three times, the reaction solution was then subjected to replacement of nitrogen gas three times once again, and finally the reaction was carried out 110° C. for 36 hours. After the reaction was complete detected by HPLC, the reaction solution was concentrated and purified by column chromatography (PE:EA=5:1) to give 0.8 g (3.1 mmol, yield 79%) of Compound 32-b (white solid).


(2) Compound 32-b (0.8 g, 3.1 mmol) was placed in a round bottom flask, added with 8 mL of water and sodium hydroxide (0.37 g, 9.3 mmol), and then reacted at 120° C. for 12 h. After the reaction was complete detected by TLC, the reaction solution was extracted three times with 30 mL of dichloromethane. The aqueous phase was adjusted to pH 2 with 1N HCl solution, and a white solid was precipitated, which was filtered to give a filter cake, and dried to give 0.65 g (2.7 mmol, yield 87%) of Compound 32.


4. Synthesis of Compound 207




embedded image


(1) Compound II (1 g, 3.9 mmol), Compound 207-a (0.83 g, 5.9 mmol), and potassium carbonate (1.61 g, 11.7 mmol) were placed in a round bottom flask, added with 1,4-dioxane (10 mL)/water (1 mL) and then subjected to replacement of nitrogen gas three times, followed by the quickly addition of Pd(dppf)Cl2CH2Cl2 (0.16 g), and then subjected to replacement of nitrogen gas three times, the reaction solution was then subjected to replacement of nitrogen gas three times once again, and finally the reaction was carried out at 110° C. for 36 hours. After the reaction was complete detected by HPLC, the reaction solution was concentrated and purified by column chromatography (PE:EA=3:1) to give 0.57 g (2.1 mmol, yield 53%) of Compound 207-b (white solid).


(2) Compound 207-b (0.57 g, 2.1 mmol) was placed in a round bottom flask, added with 6 mL of HBr (30%, AcOH) and reacted at 50° C. for 12 h. After the reaction was complete detected by HPLC, the reaction solution was cooled to room temperature, added with water to precipitate, and filtered to obtain a white solid, which was dried to give 0.25 g (1.0 mmol, yield 47%) of Compound 207.


5. Synthesis of Compound 211




embedded image


(1) Compound




embedded image


(1.0 g, 5.8 mmol, 1.0 eq), bis-boronic acid pinacol ester (1.6 g, 6.38 mmol, 1.1 eq), and potassium acetate (1.1 g, 11.6 mmol, 2.0 eq) were placed in a 100 mL round bottom flask, added with toluene (40 mL) and then subjected to replacement of nitrogen gas once, followed by the quickly addition of Pd(dppf)Cl2CH2Cl2 (237 mg, 0.29 mmol, 0.05 eq), and then subjected to replacement of nitrogen gas three times, and then heated to 120° C. and reacted for 16 h. The system was cooled to room temperature, and Compound II (1.48 g, 5.8 mmol, 1.0 eq), K2CO3 (1.6 g, 11.6 mmol, 2.0 eq), 95% ethanol (8 mL) and Pd(dppf)Cl2CH2Cl2 (237 mg, 0.29 mmol, 0.05 eq) were added, and then subjected to replacement of nitrogen gas three times, and heated to 120° C. (reflux) and reacted for 4 h. After the reaction was complete detected by LCMS, the reaction mixture was concentrated and then added with silica gel and purified by column chromatography to give obtain Compound 211-b (560 mg, Y: 36%).


(2) Compound 211-b (0.56 g, 2.0 mmol) was placed in a round bottom flask, added with AcOK (0.98 g, 10 mmol) and DMSO (5.6 mL) and then reacted at 125° C. for 3 h. After the reaction was complete, the temperature was lowered. The reaction solution was added with 20 mL of water, extracted three times with 30 mL of dichloromethane, and the aqueous phase was adjusted to pH 6 with 1N HCl solution, and a white solid was precipitated, which was filtered to obtain a filter cake, and dried to give 0.26 g of Compound 211 (1.6 mmol, yield 50%).


6. Synthesis of Compound 733




embedded image


(1) experimental apparatus: a 50 mL round bottom single-necked flask, a magnetic stirrer, and a thermostatic magnetic stirrer.


Compound II (1 g, 3.9 mmol), Compound 733-a (0.83 g, 5.9 mmol), and cesium carbonate (3.81 g, 11.7 mmol) were placed in the round bottom flask, added with 1,4-dioxane (20 mL)/water (5 mL) and then subjected to replacement of nitrogen gas three times, followed by the quickly addition of Pd(dppf)Cl2CH2Cl2 (0.16 g), and then subjected to replacement of nitrogen gas three times, and then the reaction solution was subjected to replacement of nitrogen gas three times once again, and finally the reaction was carried out at 100° C. for 36 hours. After the reaction was complete detected by HPLC, the reaction system was concentrated and purified by column chromatography to give 0.6 g (2.2 mmol, yield: 56%) of Compound 733-b (white solid).


(2) experimental apparatus: a 50 mL round bottom single-necked flask, a magnetic stirrer, a thermostatic magnetic stirrer, and a spherical condenser.


Compound 733-b (0.6 g, 2.2 mmol) was placed in the round bottom flask, added with 8 mL of water and sodium hydroxide (0.26 g, 6.6 mmol) and reacted at 80° C. for 12 h. After the reaction was complete, the reaction solution was extracted three times with 30 mL of dichloromethane, the aqueous phase was adjusted to pH 2 with 1N HCl solution, and a white solid was precipitated, a filter cake was obtained by filtration, and the filter cake was dried to give 0.41 g (1.6 mmol, yield 73%) of Compound 733.


7. Synthesis of Compound 734




embedded image


(1) experimental apparatus: a 50 mL round bottom single-necked flask, a magnetic stirrer, and a thermostatic magnetic stirrer.


Compound II (1 g, 3.9 mmol), Compound 734-a (1.0 g, 5.9 mmol), and cesium carbonate (3.81 g, 11.7 mmol) were placed in the round bottom flask, added with 1,4-dioxane (20 mL)/water (5 mL) and then subjected to replacement of nitrogen three times, followed by the quickly addition of Pd(dppf)Cl2CH2Cl2 (0.16 g), and subjected to replacement of nitrogen gas three times, then the reaction solution was subjected to replacement of nitrogen gas three times once again, and finally the reaction was carried out at 110° C. for 36 hours. After the reaction was complete detected by HPLC, the reaction system was concentrated and purified by column chromatography to give 0.7 g (2.3 mmol, yield 57%) of Compound 734-b (white solid).


(2) experimental apparatus: a 50 mL round bottom single-necked flask, a magnetic stirrer, a thermostatic magnetic stirrer, and a spherical condenser.


Compound 734-b (0.7 g, 2.3 mmol) was placed in the round bottom flask, added with 15 mL of water, sodium hydroxide (0.27 g, 6.9 mmol), and then reacted at 90° C. for 12 h. After the reaction was complete, the reaction solution was extracted three time with 30 mL of dichloromethane, the aqueous phase was adjusted to pH 2 with 1N HCl solution, and a white solid was precipitated, which was filtered to obtain a filter cake, and dried to give 0.41 g (1.6 mmol, yield 73%) of Compound 734.


8. Synthesis of Compound 744




embedded image


(1) Compound II (1 g, 3.9 mmol) was placed in a round bottom flask, added with dioxane: H2O=3:1 (10 mL), sodium hydroxide (0.23 g, 5.8 mmol), and then reacted at 120° C. for 5 h. After the reaction was complete detected by TLC, the reaction solution was subjected to rotary evaporation to remove the solvent, added with 20 mL of water, and then extracted three times with 20 mL of dichloromethane. The aqueous phase was adjusted to pH 2 with 1N HCl solution, and a white solid was precipitated, which was dried to give 0.6 g (2.5 mmol, yield 65%) of Compound 744-b.


(2) Compound 744-b (1 g, 4.1 mmol), Compound 744-a (0.96 g, 6.1 mmol), and potassium carbonate (1.69 g, 12.3 mmol) were placed in a round bottom flask, added with 1,4-dioxane (10 mL)/water (1 mL) and then subjected to replacement of nitrogen gas three times, followed by the quickly addition of Pd(dppf)Cl2CH2Cl2 (0.16 g), and then subjected to replacement of nitrogen gas three times, and then the reaction solution was subjected to replacement of nitrogen gas three times once again, and finally the reaction was carried out at 110° C. for 36 hours. After the reaction was complete detected by HPLC, the reaction mixture was concentrated, then added with 20 mL of water, and extracted three times with 30 mL of dichloromethane. The aqueous phase was adjusted to pH 4 with 1N HCl solution, and a white solid was precipitated, which was filtered to obtain a filter cake, and then dried to give 0.51 g of Compound 744 (1.85 mmol, yield 45%).


9. Synthesis of Compound 770




embedded image


(1) Compound II (1 g, 3.9 mmol), Compound 770-a (0.92 g, 5.9 mmol), and cesium carbonate (3.81 g, 11.7 mmol) were placed in a round bottom flask, added with 1,4-dioxane (10 mL)/water (1 mL) and then subjected to replacement of nitrogen gas three times, followed by the quickly addition of Pd(dppf)Cl2CH2Cl2 (0.16 g) and then subjected to replacement of nitrogen gas three times, then the reaction solution was subjected to replacement of nitrogen gas three times once again, and finally the reaction was carried out at 110° C. for 36 hours. After the reaction was complete detected by HPLC, the reaction solution was directly concentrated and purified by column chromatography (PE:EA=3:1) to give 0.63 g (2.3 mmol, yield 58.9%) of Compound 770-b (white solid).


(2) Compound 770-b (0.63 g, 2.3 mmol) was placed in a round bottom flask, added with AcOK (1.12 g, 11.5 mmol) and DMSO (6.3 mL) and reacted at 125° C. for 3 h. After the reaction was complete, the temperature was lowered. The reaction solution was added with 20 mL of water, and extracted three times with 30 mL of dichloromethane. The aqueous phase was adjusted to pH 6 with 1N HCl solution, and a white solid was precipitated, which was filtered to obtain a filter cake, and dried to give 0.41 g of Compound 770 (1.6 mmol, yield 73%).


10. Synthesis of Compound 774




embedded image


(1) Compound II (1 g, 3.9 mmol), Compound 774-a (0.737 g, 5.9 mmol), and potassium carbonate (1.62 g, 11.7 mmol) were placed in a round bottom flask, added with 1,4-dioxane (10 mL)/water (1 mL) and then subjected to replacement of nitrogen gas three times, then followed by the quickly addition of Pd(dppf)Cl2CH2Cl2 (0.16 g), and then subjected to replacement of nitrogen gas three times, then the reaction solution was subjected to replacement of nitrogen gas three times once again, and finally the reaction was carried out at 110° C. for 36 hours. After the reaction was complete detected by HPLC, the reaction solution was concentrated and purified by column chromatography (PE:EA=5:1) to give 0.82 g (3.2 mmol, yield 83%) of Compound 774-b (white solid).


(2) Compound 774-b (0.82 g, 3.2 mmol) was placed in a round bottom flask, added with AcOK (1.56 g, 16 mmol) and DMSO (8.3 mL) and reacted at 120° C. for 3 h. After the reaction was complete, the temperature was lowered. The reaction solution was added with 20 mL of water, and extracted with three time with 30 mL of dichloromethane. The aqueous phase was adjusted to pH 4 with 1N HCl solution, and a white solid was precipitated, which was filtered to obtain a filter cake, and then dried to give 0.50 g of Compound 774 (2.08 mmol, Yield 65%).


11. Synthesis of Compound 1-39




embedded image


Compound 32 (1 eq.),




embedded image


(1.1 eq.), potassium carbonate (1.5 eq.) and acetonitrile (5 V, V represents per gram of substrate corresponding to 1 mL of acetonitrile, similarly hereinafter) were added at room temperature into a 50 mL single-mouth eggplant-shaped bottle, stirred for 1 h at a controlled temperature of 20° C. After the reaction was complete detected by TLC, the reaction system was subjected to a rotary evaporator to remove acetonitrile, added with with water-ethyl acetate for extraction, the residue was separated by column chromatography with silica gel (100 mesh to 200 mesh) to give the product in a yield of 79%.


12. Synthesis of Compound 1-127




embedded image


Compound 744 (1 eq.),




embedded image


(2 eq.), potassium carbonate (3 eq.) and acetonitrile (10 V) were added into a 50 mL single-mouth eggplant-shaped flask at room temperature, and stirred at a controlled temperature of 80° C. for 12 h. After the reaction was complete detected by TLC, the reaction system was subjected to a rotary evaporator to remove acetonitrile, added with water-ethyl acetate for extraction. The residue was separated by column chromatography with silica gel (100 mesh to 200 mesh) to give a product in yield of 83%.


13. Synthesis of Compound 1-170




embedded image


Referring to the synthesis method of Compound 1, Compound 4 was prepared, and then Compound 4-1 was prepared according to the synthesis method disclosed in WO2012142162A2. Finally, Compound 4-1 (1 eq.).),




embedded image


(1.1 eq.), potassium carbonate (3 eq.) and acetonitrile (10 V) were added into a 50 mL single-mouth eggplant-shaped bottle at room temperature, hearted to 80° C., and stirred for 12 h. After the reaction was complete detected by TLC, the reaction system was subjected to a rotary evaporator to remove acetonitrile, and the residue was separated by column chromatography with silica gel (100 mesh to 200 mesh) to give a product in yield of 68%.


14. Synthesis of Compound 1-213




embedded image


Compound 744 (1 eq.),




embedded image


(1.5 eq.), triethylamine (3 eq.) and dichloromethane (10 V) were added into a 50 mL single-mouth eggplant-shaped flask at room temperature, and stirred at a controlled temperature of 40° C. for 1 h. After the reaction was complete detected by TLC, the reaction system was subjected to a rotary evaporator to remove dichloromethane, and added with water-ethyl acetate for extraction. The residue was separated by column chromatography with silica gel (100 mesh to 200 mesh) to give a product in yield of 72%.


15. Synthesis of Compound 1-242




embedded image


Compound 1 (1 eq.),




embedded image


(1.1 eq.), potassium carbonate (3 eq.) and acetonitrile (10 V) were added into a 50 mL single-mouth eggplant-shaped bottle at room temperature, and stirred at room temperature for 30 min. After the reaction was complete detected by TLC, the reaction system was subjected to distillation under reduced pressure to remove acetonitrile, then added with water (5V) for dissolution and extracted with ethyl acetate (5V*3). The ethyl acetate was removed by evaporation under reduced pressure, and the residue was purified by column chromatography with silica gel (100 mesh to 200 mesh) to give a product as Compound 1-242 in yield of 85%.


16. Synthesis of Compound 1-243




embedded image


Compound 1 (1 eq.), triethylamine (3 eq.) and dichloromethane (5 V) were added into a 50 mL single-mouth eggplant-shaped flask under ice bath, and added dropwise with




embedded image


(1.2 eq.) under ice bath, then stirred at room temperature for 30 min. After the reaction was complete detected by TLC, the reaction system was added with water (5V) and extracted with dichloromethane (5V*3). The dichloromethane was removed by distillation under reduced pressure, and the residue was separated by column chromatography with silica gel (100 mesh to 200 mesh) to give a product as Compound 1-243 in yield of 78%.


17. Synthesis of Compound 1-244




embedded image


Compound 1 (1 equivalent), Phenofluor (1.5 equivalent), cesium fluoride (3 equivalents), and toluene (10 V) were added into a 50 mL single-mouth eggplant-shaped bottle at room temperature, heated to 80° C. and stirred for 18 h. After the reaction was complete detected by TLC, intermediate Compound 1-244-a was obtained after workup. Compound 1-244-a (1 eq.),




embedded image


(1.2 eq.), potassium carbonate (3 eq.) and acetonitrile (10 V) were added to another 50 mL single-mouth eggplant-shaped bottle, heated to 80° C. and stirred for 18 h. After the reaction was complete detected by TLC, the reaction system was subjected to evaporation under reduced pressure to remove acetonitrile, then added with water (5V) for dissolution and extracted with ethyl acetate (5V*3). The ethyl acetate was removed by evaporation under reduced pressure, and the residue was purified by column chromatography with silica gel (100 mesh to 200 mesh) to give a product as Compound 1-244 in yield of 69%.


18. Synthesis of Compound 1-245




embedded image


Compound 1 (1 eq.), POCl3 (1.5 eq.), 1,2-dichloroethane (10 V), and 5% N,N— dimethylformamide were added into a 50 mL single-mouth eggplant-shaped bottle at room temperature, heated to 80° C. and stirred for 6 h. After the reaction was complete detected by TLC, water (5V) was added for dissolution, and then extraction was carried out with 1,2-dichloroethane (5V*3). The 1,2-dichloroethane was removed by distillation under reduced pressure to give Compound 1-245-a. Compound 1-245-a (1 eq.),




embedded image


(1.2 eq.), potassium hydroxide (3 eq.) and N,N-dimethylformamide (10 V) were added at room temperature into another 50 mL single-mouth eggplant-shaped bottle, heated to 100° C., and stirred for 18 h. After the reaction was complete detected by TLC, water (5 V) was added for dissolution, and then extraction was carried out with ethyl acetate (5 V*3). The ethyl acetate was removed by distillation under reduced pressure, and the residue was separated by column chromatography with silica gel (100 mesh to 200 mesh) to give a product as Compound 1-245 in a yield of 52%.


The compounds in Table 1 and Table 2 are prepared by the methods described above.


Evaluation of Biological Activity:


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


Level 10: completely dead;


Level 9: above 90% growth inhibition rate;


Level 8: above 80% growth inhibition rate;


Level 7: above 70% growth inhibition rate;


Level 6: above 60% growth inhibition rate;


Level 5: above 50% growth inhibition rate;


Level 4: above 40% growth inhibition rate;


Level 3: above 30% growth inhibition rate;


Level 2: above 20% growth inhibition rate;


Level 1: below 20% growth inhibition rate;


Level 0: no effect.


The above described growth inhibition rates are fresh weight inhibition rates.


Experiment of post-emergence test: monocotyledonous and dicotyledonous weed seeds as well as main crop seeds (i.e., wheat, corn, rice, soybean, cotton, oilseed rape, millet and sorghum) were put into a plastic pot loaded with soil, then covered with 0.5-2 cm of soil, and the seeds were allowed to grow in good greenhouse environment. The test plants were treated at 2-3 leaf stage 2-3 weeks after sowing. The test compounds of the invention were dissolved in acetone respectively, then added with Tween-80 and diluted by a certain amount of water to give solutions with certain concentrations, and added with 80% vegetable oil methyl ester synergist at 1500 g/ha. The solution was sprayed to the plants with a sprayer. The plants were cultured for 3 weeks in the greenhouse. The experiment results of weed controlling effect after 3 weeks were listed in Table 3 and Table 4.









TABLE 3







Experiment on weed control effect of compounds


of Formula I in Post-emergence stage












Compound

Amaranthus


Rorippa


Veronica

Chenopo-



No.

retroflexus


indica


polita

diaceae
Dose















1
10
10
10
8
2000 g/ha


4
10
10
10
8
2000 g/ha


8
10
10
10
8
2000 g/ha


24
10
10
10
10
2000 g/ha


26
10
10
10
10
1000 g/ha


27
10
10
10
10
1000 g/ha


28
10
10
10
10
1000 g/ha


29
10
10
10
10
1000 g/ha


30
10
10
10
10
1000 g/ha


31
10
10
10
10
1000 g/ha


32
10
10
10
10
1000 g/ha


33
10
10
10
10
1000 g/ha


34
10
10
10
10
1000 g/ha


35
10
10
10
10
1000 g/ha


36
10
10
10
10
1000 g/ha


37
10
10
10
10
1000 g/ha


38
10
10
10
10
1000 g/ha


39
10
10
10
10
1000 g/ha


40
10
10
10
10
1000 g/ha


41
10
10
10
10
1000 g/ha


42
10
10
10
10
1000 g/ha


43
10
10
10
10
1000 g/ha


44
10
10
10
10
1000 g/ha


45
10
10
10
10
1000 g/ha


46
10
10
10
10
1000 g/ha


47
10
10
10
10
1000 g/ha


48
10
10
10
10
1000 g/ha


49
10
10
10
10
1000 g/ha


50
10
10
10
10
1000 g/ha


51
10
10
10
10
1000 g/ha


52
10
10
10
10
1000 g/ha


53
10
10
10
10
1000 g/ha


54
10
10
10
10
1000 g/ha


55
10
10
10
10
1000 g/ha


56
10
10
10
10
1000 g/ha


57
10
10
10
10
1000 g/ha


58
10
10
10
10
1000 g/ha


59
10
10
10
10
1000 g/ha


60
10
10
10
10
1000 g/ha


61
10
10
10
10
1000 g/ha


62
10
10
10
10
1000 g/ha


63
10
10
10
10
1000 g/ha


64
10
10
10
10
1000 g/ha


65
10
10
10
10
1000 g/ha


66
10
10
10
10
1000 g/ha


67
10
10
10
10
1000 g/ha


68
10
10
10
10
1000 g/ha


69
10
10
10
10
1000 g/ha


70
10
10
10
10
1000 g/ha


71
10
10
10
10
1000 g/ha


72
10
10
10
10
1000 g/ha


77
10
10
10
10
2000 g/ha


81
10
10
10
10
1000 g/ha


82
10
10
10
10
1000 g/ha


83
10
10
10
10
1000 g/ha


92
10
10
10
10
1000 g/ha


93
10
10
10
10
1000 g/ha


94
10
10
10
10
1000 g/ha


95
10
10
10
10
1000 g/ha


96
10
10
10
10
1000 g/ha


97
10
10
10
10
1000 g/ha


111
10
10
10
10
1000 g/ha


114
10
10
10
10
1000 g/ha


128
10
10
10
10
1000 g/ha


163
10
10
10
10
2000 g/ha


165
10
10
10
10
2000 g/ha


166
10
10
10
10
2000 g/ha


168
10
10
10
10
2000 g/ha


169
10
10
10
10
2000 g/ha


173
10
10
10
10
2000 g/ha


179
10
10
10
10
2000 g/ha


202
10
10
10
10
2000 g/ha


204
10
10
10
10
2000 g/ha


205
10
10
10
10
2000 g/ha


206
10
10
10
10
2000 g/ha


207
10
10
10
10
2000 g/ha


211
10
10
10
10
2000 g/ha


212
10
10
10
10
2000 g/ha


214
10
10
10
10
2000 g/ha


218
10
10
10
10
2000 g/ha


219
10
10
10
10
2000 g/ha


220
10
10
10
10
2000 g/ha


221
10
10
10
10
2000 g/ha


222
10
10
10
10
2000 g/ha


223
10
10
10
10
2000 g/ha


224
10
10
10
10
2000 g/ha


225
10
10
10
10
2000 g/ha


226
10
10
10
10
2000 g/ha


227
10
10
10
10
2000 g/ha


231
10
10
10
10
2000 g/ha


236
10
10
10
10
2000 g/ha


263
10
10
10
10
2000 g/ha


279
10
10
10
10
2000 g/ha


323
10
10
10
10
2000 g/ha


349
10
10
10
10
2000 g/ha


370
10
10
10
10
2000 g/ha


371
10
10
10
10
2000 g/ha


380
10
10
10
10
2000 g/ha


414
10
10
10
10
3000 g/ha


418
10
10
10
10
3000 g/ha


439
10
10
10
10
3000 g/ha


540
10
10
10
10
3000 g/ha


543
10
10
10
10
3000 g/ha


544
10
10
10
10
3000 g/ha


546
10
10
10
10
3000 g/ha


570
10
10
10
10
3000 g/ha


588
10
10
10
10
3000 g/ha


589
10
10
10
10
3000 g/ha


594
10
10
10
10
3000 g/ha


595
10
10
10
10
3000 g/ha


597
10
10
10
10
3000 g/ha


613
10
10
10
10
3000 g/ha


634
10
10
10
10
3000 g/ha


636
10
10
10
10
3000 g/ha


637
10
10
10
10
3000 g/ha


714
10
10
10
10
3000 g/ha


723
10
10
10
10
3000 g/ha


732
10
10
10
10
1000 g/ha


733
10
10
10
10
1000 g/ha


734
10
10
10
10
1000 g/ha


735
10
10
10
10
1000 g/ha


736
10
10
10
10
1000 g/ha


737
10
10
10
10
3000 g/ha


739
10
10
10
10
3000 g/ha


740
10
10
10
10
3000 g/ha


741
10
10
10
10
3000 g/ha


742
10
10
10
10
3000 g/ha


743
10
10
10
10
3000 g/ha


744
10
10
10
10
3000 g/ha


745
10
10
10
10
3000 g/ha


746
10
10
10
10
3000 g/ha


753
10
10
10
10
3000 g/ha


755
10
10
10
10
3000 g/ha


761
10
10
10
10
3000 g/ha


762
10
10
10
10
3000 g/ha


763
10
10
10
10
3000 g/ha


764
10
10
10
10
3000 g/ha


766
10
10
10
10
3000 g/ha


768
10
10
10
10
3000 g/ha


769
10
10
10
10
3000 g/ha


770
10
10
10
10
3000 g/ha


771
10
10
10
10
3000 g/ha


772
10
10
10
10
3000 g/ha


774
10
10
10
10
3000 g/ha


775
10
10
10
10
3000 g/ha


776
10
10
10
10
3000 g/ha


777
10
10
10
10
3000 g/ha


778
10
10
10
10
3000 g/ha


779
10
10
10
10
3000 g/ha


780
10
10
10
10
3000 g/ha


781
10
10
10
10
3000 g/ha


782
10
10
10
10
3000 g/ha


783
10
10
10
10
3000 g/ha


784
10
10
10
10
3000 g/ha


787
10
10
10
10
3000 g/ha


791
10
10
10
10
3000 g/ha


794
10
10
10
10
3000 g/ha


803
10
10
10
10
3000 g/ha


804
10
10
10
10
3000 g/ha


805
10
10
10
10
3000 g/ha


806
10
10
10
10
3000 g/ha


807
10
10
10
10
3000 g/ha


808
10
10
10
10
3000 g/ha


809
10
10
10
10
3000 g/ha


810
10
10
10
10
3000 g/ha


811
10
10
10
10
3000 g/ha


812
10
10
10
10
3000 g/ha


813
10
10
10
10
3000 g/ha


816
10
10
10
10
3000 g/ha


820
10
10
10
10
3000 g/ha


823
10
10
10
10
3000 g/ha


824
10
10
10
10
3000 g/ha


825
10
10
10
10
3000 g/ha


826
10
10
10
10
3000 g/ha


827
10
10
10
10
3000 g/ha


828
10
10
10
10
3000 g/ha


829
10
10
10
10
3000 g/ha


830
10
10
10
10
3000 g/ha


831
10
10
10
10
3000 g/ha


832
10
10
10
10
3000 g/ha


833
10
10
10
10
3000 g/ha


834
10
10
10
10
3000 g/ha


839
10
10
10
10
3000 g/ha


844
10
10
10
10
2000 g/ha


857
10
10
10
10
3000 g/ha


873
10
10
10
10
3000 g/ha


877
10
10
10
10
3000 g/ha


963
10
10
10
10
3000 g/ha


964
10
10
10
10
3000 g/ha


965
10
10
10
10
3000 g/ha


966
10
10
10
10
3000 g/ha


967
10
10
10
10
3000 g/ha


968
10
10
10
10
3000 g/ha


969
10
10
10
10
3000 g/ha


970
10
10
10
10
3000 g/ha


971
10
10
10
10
3000 g/ha


972
10
10
10
10
3000 g/ha


973
10
10
10
10
3000 g/ha


974
10
10
10
10
3000 g/ha


975
10
10
10
10
3000 g/ha


976
10
10
10
10
3000 g/ha


977
10
10
10
10
3000 g/ha


978
10
10
10
10
3000 g/ha


979
10
10
10
10
3000 g/ha


980
10
10
10
10
3000 g/ha


983
10
10
10
10
3000 g/ha


984
10
10
10
10
3000 g/ha


986
10
10
10
10
3000 g/ha


987
10
10
10
10
3000 g/ha


988
10
10
10
10
3000 g/ha


989
10
10
10
10
3000 g/ha


990
10
10
10
10
3000 g/ha


991
10
10
10
10
3000 g/ha


992
10
10
10
10
3000 g/ha


993
10
10
10
10
3000 g/ha


994
10
10
10
10
3000 g/ha


995
10
10
10
10
3000 g/ha


996
10
10
10
10
3000 g/ha


997
10
10
10
10
3000 g/ha


998
10
10
10
10
3000 g/ha


999
10
10
10
10
3000 g/ha


1000
10
10
10
10
3000 g/ha


1001
10
10
10
10
3000 g/ha


1002
10
10
10
10
3000 g/ha


1003
10
10
10
10
3000 g/ha


1004
10
10
10
10
3000 g/ha


1005
10
10
10
10
3000 g/ha


1006
10
10
10
10
3000 g/ha


1007
10
10
10
10
3000 g/ha


1008
10
10
10
10
3000 g/ha


1018
10
10
10
10
3000 g/ha


1076
10
10
10
10
3000 g/ha


1081
10
10
10
10
3000 g/ha


1286
10
10
10
10
3000 g/ha


1522
10
N
N
10
3000 g/ha


1523
10
10
10
10
3000 g/ha


1524
10
10
10
10
3000 g/ha





Note:


N means no data.













TABLE 4







Experiment on weed control effect of derivatives


of Formula I-1 in Post-emergence stage












Compound

Amaranthus


Rorippa


Veronica

Chenopo-



No.

retroflexus


indica


polita

diaceae
Dose















1-1
10
10
10
10
3000 g/ha


1-2
10
10
10
10
3000 g/ha


1-3
10
10
10
10
3000 g/ha


1-4
10
10
10
10
3000 g/ha


1-7
10
10
10
10
3000 g/ha


1-8
10
10
10
10
3000 g/ha


1-9
10
10
10
10
3000 g/ha


1-10
10
10
10
10
3000 g/ha


1-14
10
10
10
10
3000 g/ha


1-15
10
10
10
10
3000 g/ha


1-16
10
10
10
10
3000 g/ha


1-17
10
10
10
10
3000 g/ha


1-18
10
10
10
10
3000 g/ha


1-19
10
10
10
10
3000 g/ha


1-22
10
10
10
10
3000 g/ha


1-23
10
10
10
10
3000 g/ha


1-25
10
10
10
10
3000 g/ha


1-26
10
10
10
10
3000 g/ha


1-29
10
10
10
10
3000 g/ha


1-30
10
10
10
10
3000 g/ha


1-31
10
10
10
10
3000 g/ha


1-33
10
10
10
10
3000 g/ha


1-35
10
10
10
10
3000 g/ha


1-36
10
10
10
10
3000 g/ha


1-38
10
10
10
10
3000 g/ha


1-39
10
10
10
10
3000 g/ha


1-40
10
10
10
10
3000 g/ha


1-42
10
10
10
10
3000 g/ha


1-43
10
10
10
10
3000 g/ha


1-47
10
10
10
10
3000 g/ha


1-51
10
10
10
10
3000 g/ha


1-53
10
10
10
10
3000 g/ha


1-54
10
10
10
10
3000 g/ha


1-55
10
10
10
10
3000 g/ha


1-58
10
10
10
10
3000 g/ha


1-60
10
10
10
10
3000 g/ha


1-63
10
10
10
10
3000 g/ha


1-64
10
10
10
10
3000 g/ha


1-65
10
10
10
10
3000 g/ha


1-66
10
10
10
10
3000 g/ha


1-67
10
10
10
10
3000 g/ha


1-68
10
10
10
10
3000 g/ha


1-69
10
10
10
10
3000 g/ha


1-70
10
10
10
10
3000 g/ha


1-71
10
10
10
10
3000 g/ha


1-75
10
10
10
10
3000 g/ha


1-76
10
10
10
10
3000 g/ha


1-77
10
10
10
10
3000 g/ha


1-78
10
10
10
10
3000 g/ha


1-79
10
10
10
10
3000 g/ha


1-80
10
10
10
10
3000 g/ha


1-82
10
10
10
10
3000 g/ha


1-83
10
10
10
10
3000 g/ha


1-84
10
10
10
10
3000 g/ha


1-85
10
10
10
10
3000 g/ha


1-86
10
10
10
10
3000 g/ha


1-87
10
10
10
10
3000 g/ha


1-88
10
10
10
10
3000 g/ha


1-90
10
10
10
10
3000 g/ha


1-91
10
10
10
10
3000 g/ha


1-93
10
10
10
10
3000 g/ha


1-94
10
10
10
10
3000 g/ha


1-95
10
10
10
10
3000 g/ha


1-96
10
10
10
10
3000 g/ha


1-97
10
10
10
10
3000 g/ha


1-98
10
10
10
10
3000 g/ha


1-99
10
10
10
10
3000 g/ha


1-100
10
10
10
10
3000 g/ha


1-101
10
10
10
10
3000 g/ha


1-102
10
10
10
10
3000 g/ha


1-103
10
10
10
10
3000 g/ha


1-104
10
10
10
10
3000 g/ha


1-105
10
10
10
10
3000 g/ha


1-106
10
10
10
10
3000 g/ha


1-107
10
10
10
10
3000 g/ha


1-108
10
10
10
10
3000 g/ha


1-109
10
10
10
10
3000 g/ha


1-110
10
10
10
10
3000 g/ha


1-111
10
10
10
10
3000 g/ha


1-112
10
10
10
10
3000 g/ha


1-113
10
10
10
10
3000 g/ha


1-114
10
10
10
10
3000 g/ha


1-115
10
10
10
10
3000 g/ha


1-116
10
10
10
10
3000 g/ha


1-117
10
10
10
10
3000 g/ha


1-118
10
10
10
10
3000 g/ha


1-119
10
10
10
10
3000 g/ha


1-120
10
10
10
10
3000 g/ha


1-121
10
10
10
10
3000 g/ha


1-122
10
10
10
10
3000 g/ha


1-123
10
10
10
10
3000 g/ha


1-124
10
10
10
10
3000 g/ha


1-125
10
10
10
10
3000 g/ha


1-126
10
10
10
10
3000 g/ha


1-127
10
10
10
10
3000 g/ha


1-128
10
10
10
10
3000 g/ha


1-129
10
10
10
10
3000 g/ha


1-130
10
10
10
10
3000 g/ha


1-131
10
10
10
10
3000 g/ha


1-132
10
10
10
10
3000 g/ha


1-133
10
10
10
10
3000 g/ha


1-134
10
10
10
10
3000 g/ha


1-135
10
10
10
10
3000 g/ha


1-136
10
10
10
10
3000 g/ha


1-137
10
10
10
10
3000 g/ha


1-138
10
10
10
10
3000 g/ha


1-139
10
10
10
10
3000 g/ha


1-140
10
10
10
10
3000 g/ha


1-141
10
10
10
10
3000 g/ha


1-142
10
10
10
10
3000 g/ha


1-143
10
10
10
10
3000 g/ha


1-144
10
10
10
10
3000 g/ha


1-145
10
10
10
10
3000 g/ha


1-146
10
10
10
10
3000 g/ha


1-147
10
10
10
10
3000 g/ha


1-148
10
10
10
10
3000 g/ha


1-149
10
10
10
10
3000 g/ha


1-150
10
10
10
10
3000 g/ha


1-151
10
10
10
10
3000 g/ha


1-152
10
10
10
10
3000 g/ha


1-153
10
10
10
10
3000 g/ha


1-154
10
10
10
10
3000 g/ha


1-155
10
10
10
10
3000 g/ha


1-156
10
10
10
10
3000 g/ha


1-157
10
10
10
10
3000 g/ha


1-158
10
10
10
10
3000 g/ha


1-159
10
10
10
10
3000 g/ha


1-160
10
10
10
10
3000 g/ha


1-162
10
10
10
10
3000 g/ha


1-163
10
10
10
10
3000 g/ha


1-164
10
10
10
10
3000 g/ha


1-165
10
10
10
10
3000 g/ha


1-166
10
10
10
10
3000 g/ha


1-167
10
10
10
10
3000 g/ha


1-169
10
10
10
10
3000 g/ha


1-170
10
10
10
10
3000 g/ha


1-171
10
10
10
10
3000 g/ha


1-172
10
10
10
10
3000 g/ha


1-173
10
10
10
10
3000 g/ha


1-174
10
10
10
10
3000 g/ha


1-175
10
10
10
10
3000 g/ha


1-176
10
10
10
10
3000 g/ha


1-178
10
10
10
10
3000 g/ha


1-179
10
10
10
10
3000 g/ha


1-180
10
10
10
10
3000 g/ha


1-181
10
10
10
10
3000 g/ha


1-207
10
10
10
10
3000 g/ha


1-208
10
10
10
10
3000 g/ha


1-209
10
10
10
10
3000 g/ha


1-210
10
10
10
10
3000 g/ha


1-211
10
10
10
10
3000 g/ha


1-212
10
10
10
10
3000 g/ha


1-213
10
10
10
10
3000 g/ha


1-240
10
10
10
10
3000 g/ha









Comparative Experiment

The post-emergence test conditions were the same as above, and the results are shown in Table 5.


Control Compound A:




embedded image


Control Compound B:




embedded image


Control Compound C:




embedded image


(from patent CN106316962A)


Control Compound D:




embedded image


Control Compound E:




embedded image









TABLE 5







Results of comparison experiment
















Echinochloa


Setaria



Rorippa


Galium


Veronica




Compound

crus-galli


viridis

Chenopodiaceae

indica


aparine


polita

Dose

















32
10
10
10
10
10
10
300 g/ha


35
10
10
10
10
9
10
300 g/ha


51
6
9
10
10
8
9
300 g/ha


202
7
10
10
10
10
8
300 g/ha


206
10
10
10
10
10
10
300 g/ha


207
10
10
10
10
10
10
300 g/ha


220
10
10
10
10
10
10
300 g/ha


733
10
10
10
10
10
10
300 g/ha


739
10
10
10
10
8
10
300 g/ha


740
10
10
10
10
10
10
300 g/ha


744
10
10
10
10
10
10
300 g/ha


779
10
10
10
10
10
10
300 g/ha


844
10
10
10
10
10
10
150 g/ha


1000
10
10
10
10
10
10
300 g/ha


1524
N
10
10
10
9
9
300 g/ha


1-39
10
10
10
10
10
10
150 g/ha


1-43
10
10
10
10
10
10
150 g/ha


1-55
10
10
10
10
10
10
150 g/ha


1-82
7
10
10
10
7
8
150 g/ha


1-86
10
10
10
10
10
10
150 g/ha


A
0
3
5
2
5
3
300 g/ha


B
0
3
3
3
4
3
300 g/ha


C
0
0
3
3
2
2
300 g/ha


D
0
0
1
1
0
0
300 g/ha


E
0
0
1
1
0
0
300 g/ha





Note:


N means no data.






It can be seen from the above table, the compounds of the present invention have superior herbicidal activity compared with the control compounds.


In addition, after testing, the compounds of the present invention have good selectivity for crops when being applied preemergence or postemergence, especially for wheat, rice, soybean, cotton, corn, sorghum, millet and other crops.


Experiment of Pre-Emergence Test:


Seeds of monocotyledonous and dicotyledonous weeds and main crops (e.g. wheat, corn, rice, soybean, cotton, oilseed rape, millet and sorghum) were put into a plastic pot loaded with soil and covered with 0.5-2 cm of soil. The test compounds of the present invention was dissolved with acetone, then added with Tween-80, diluted by a certain amount of water to reach a certain concentration, and sprayed immediately after sowing. The obtained seeds were incubated for 4 weeks in the greenhouse after spraying. The test results were observed 3 weeks later. It was observed that the herbicides of the present invention mostly had excellent effect at dose of 250 g/ha, especially to weeds such as Echinochloa crusgalli, Digitaria sanguinalis and Abutilon theophrasti, etc., and many compounds had good selectivity for corn, wheat, rice, soybean, oilseed rape, etc.


It is found in the experiment that the compounds of the present invention generally have good weed control efficacy, especially for major broadleaf weeds such as Abutilon theophrasti and Bidens bipinnata, etc., which are widely occurred in corn, rice and wheat fields, and have excellent commercial value. Above all, it is noted that the compound of the invention have extremely high activity to broadleaf weeds, which are resistant to ALS inhibitor, like corn gromwell, cleavers and chickweed, 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 tripartite and Sagittaria trifolia L. were sowed and gently covered with soil, then left to stand still in greenhouse in the state of 0.5-1 cm of water storage. The tuber of Sagittaria trifolia L. was planted in the next day or 2 days later. It was kept at 3-4 cm of water storage thereafter. The weeds were treated by dripping the WP or SC water diluents prepared according to the common preparation method of the compounds of the present invention with pipette homogeneously to achieve specified effective amount when Echinochloa crusgalli, Scirpus juncoides and Bidens tripartite reached 0.5 leaf stage and Sagittaria trifolia L. reached the time point of primary leaf stage.


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 tripartite and Sagittaria trifolia L. 14 days after the treatment of the compound of the invention and the fertility condition of rice 21 days after the treatment of the compound of the invention respectively with the naked eye. Evaluate the weed control effect with 1-10 activity standard level. It has been found that many of the compounds of the present invention have excellent activity and selectivity, especially for Sagittaria trifolia L. and Echinochloa crusgalli.


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


Further, the present invention also relates to a herbicidal composition comprising component (i) (such as the compound of Formula I) and component (ii), and some of the compositions are as follows:


1 (Compound No. as shown in Table 1, similarly hereinafter)+Sulcotrione, 1+Mesotrione, 1+Topramezone, 1+Tembotrione, 1+Bicyclopyrone, 1+Tefuryltrione, 1+Benzobicyclon, 1+Lancotrione, 1+Shuangzuocaotong, 1+Huanbifucaotong, 1+Sanzuohuangcaotong, 1+Benzuofucaotong, 1+Pyrasulfotole, 1+Pyrazolate, 1+Benzofenap, 1+Tolpyralate, 1+Fenquinotrione, 1+Isoxaflutole, 1+Fluroxypyr or esters thereof, 1+Halauxifen-methyl, 1+Florpyrauxifen-benzyl, 1+Quinclorac, 1+Quinmerac, 1+Chipton or salts/esters thereof, 1+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 1+MCPB or salts/esters thereof, 1+2,4-D or salts/esters thereof, 1+Dichlorprop or salts/esters thereof, 1+2,4-DB or salts/esters thereof, 1+Dicamba, 1+Picloram, 1+Trichlopyr, 1+Clopyralid, 1+Triclopyr, 1+Flurochloridone, 1+Flurtamone, 1+Diflufenican, 1+Picolinafen, 1+Beflubutamid, 1+Norflurazon, 1+Fluridone.


2+Sulcotrione, 2+Mesotrione, 2+Topramezone, 2+Tembotrione, 2+Bicyclopyrone, 2+Tefuryltrione, 2+Benzobicyclon, 2+Lancotrione, 2+Shuangzuocaotong, 2+Huanbifucaotong, 2+Sanzuohuangcaotong, 2+Benzuofucaotong, 2+Pyrasulfotole, 2+Pyrazolate, 2+Benzofenap, 2+Tolpyralate, 2+Fenquinotrione, 2+Isoxaflutole, 2+Fluroxypyr or esters thereof, 2+Halauxifen-methyl, 2+Florpyrauxifen-benzyl, 2+Quinclorac, 2+Quinmerac, 2+Chipton or salts/esters thereof, 2+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 2+MCPB or salts/esters thereof, 2+2,4-D or salts/esters thereof, 2+Dichlorprop or salts/esters thereof, 2+2,4-DB or salts/esters thereof, 2+Dicamba, 2+Picloram, 2+Trichlopyr, 2+Clopyralid, 2+Triclopyr, 2+Flurochloridone, 2+Flurtamone, 2+Diflufenican, 2+Picolinafen, 2+Beflubutamid, 2+Norflurazon, 2+Fluridone.


3+Sulcotrione, 3+Mesotrione, 3+Topramezone, 3+Tembotrione, 3+Bicyclopyrone, 3+Tefuryltrione, 3+Benzobicyclon, 3+Lancotrione, 3+Shuangzuocaotong, 3+Huanbifucaotong, 3+Sanzuohuangcaotong, 3+Benzuofucaotong, 3+Pyrasulfotole, 3+Pyrazolate, 3+Benzofenap, 3+Tolpyralate, 3+Fenquinotrione, 3+Isoxaflutole, 3+Fluroxypyr or esters thereof, 3+Halauxifen-methyl, 3+Florpyrauxifen-benzyl, 3+Quinclorac, 3+Quinmerac, 3+Chipton or salts/esters thereof, 3+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 3+MCPB or salts/esters thereof, 3+2,4-D or salts/esters thereof, 3+Dichlorprop or salts/esters thereof, 3+2,4-DB or salts/esters thereof, 3+Dicamba, 3+Picloram, 3+Trichlopyr, 3+Clopyralid, 3+Triclopyr, 3+Flurochloridone, 3+Flurtamone, 3+Diflufenican, 3+Picolinafen, 3+Beflubutamid, 3+Norflurazon, 3+Fluridone.


4+Sulcotrione, 4+Mesotrione, 4+Topramezone, 4+Tembotrione, 4+Bicyclopyrone, 4+Tefuryltrione, 4+Benzobicyclon, 4+Lancotrione, 4+Shuangzuocaotong, 4+Huanbifucaotong, 4+Sanzuohuangcaotong, 4+Benzuofucaotong, 4+Pyrasulfotole, 4+Pyrazolate, 4+Benzofenap, 4+Tolpyralate, 4+Fenquinotrione, 4+Isoxaflutole, 4+Fluroxypyr or esters thereof, 4+Halauxifen-methyl, 4+Florpyrauxifen-benzyl, 4+Quinclorac, 4+Quinmerac, 4+Chipton or salts/esters thereof, 4+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 4+MCPB or salts/esters thereof, 4+2,4-D or salts/esters thereof, 4+Dichlorprop or salts/esters thereof, 4+2,4-DB or salts/esters thereof, 4+Dicamba, 4+Picloram, 4+Trichlopyr, 4+Clopyralid, 4+Triclopyr, 4+Flurochloridone, 4+Flurtamone, 4+Diflufenican, 4+Picolinafen, 4+Beflubutamid, 4+Norflurazon, 4+Fluridone.


7+Sulcotrione, 7+Mesotrione, 7+Topramezone, 7+Tembotrione, 7+Bicyclopyrone, 7+Tefuryltrione, 7+Benzobicyclon, 7+Lancotrione, 7+Shuangzuocaotong, 7+Huanbifucaotong, 7+Sanzuohuangcaotong, 7+Benzuofucaotong, 7+Pyrasulfotole, 7+Pyrazolate, 7+Benzofenap, 7+Tolpyralate, 7+Fenquinotrione, 7+Isoxaflutole, 7+Fluroxypyr or esters thereof, 7+Halauxifen-methyl, 7+Florpyrauxifen-benzyl, 7+Quinclorac, 7+Quinmerac, 7+Chipton or salts/esters thereof, 7+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 7+MCPB or salts/esters thereof, 7+2,4-D or salts/esters thereof, 7+Dichlorprop or salts/esters thereof, 7+2,4-DB or salts/esters thereof, 7+Dicamba, 7+Picloram, 7+Trichlopyr, 7+Clopyralid, 7+Triclopyr, 7+Flurochloridone, 7+Flurtamone, 7+Diflufenican, 7+Picolinafen, 7+Beflubutamid, 7+Norflurazon, 7+Fluridone.


8+Sulcotrione, 8+Mesotrione, 8+Topramezone, 8+Tembotrione, 8+Bicyclopyrone, 8+Tefuryltrione, 8+Benzobicyclon, 8+Lancotrione, 8+Shuangzuocaotong, 8+Huanbifucaotong, 8+Sanzuohuangcaotong, 8+Benzuofucaotong, 8+Pyrasulfotole, 8+Pyrazolate, 8+Benzofenap, 8+Tolpyralate, 8+Fenquinotrione, 8+Isoxaflutole, 8+Fluroxypyr or esters thereof, 8+Halauxifen-methyl, 8+Florpyrauxifen-benzyl, 8+Quinclorac, 8+Quinmerac, 8+Chipton or salts/esters thereof, 8+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 8+MCPB or salts/esters thereof, 8+2,4-D or salts/esters thereof, 8+Dichlorprop or salts/esters thereof, 8+2,4-DB or salts/esters thereof, 8+Dicamba, 8+Picloram, 8+Trichlopyr, 8+Clopyralid, 8+Triclopyr, 8+Flurochloridone, 8+Flurtamone, 8+Diflufenican, 8+Picolinafen, 8+Beflubutamid, 8+Norflurazon, 8+Fluridone.


22+Sulcotrione, 22+Mesotrione, 22+Topramezone, 22+Tembotrione, 22+Bicyclopyrone, 22+Tefuryltrione, 22+Benzobicyclon, 22+Lancotrione, 22+Shuangzuocaotong, 22+Huanbifucaotong, 22+Sanzuohuangcaotong, 22+Benzuofucaotong, 22+Pyrasulfotole, 22+Pyrazolate, 22+Benzofenap, 22+Tolpyralate, 22+Fenquinotrione, 22+Isoxaflutole, 22+Fluroxypyr or esters thereof, 22+Halauxifen-methyl, 22+Florpyrauxifen-benzyl, 22+Quinclorac, 22+Quinmerac, 22+Chipton or salts/esters thereof, 22+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 22+MCPB or salts/esters thereof, 22+2,4-D or salts/esters thereof, 22+Dichlorprop or salts/esters thereof, 22+2,4-DB or salts/esters thereof, 22+Dicamba, 22+Picloram, 22+Trichlopyr, 22+Clopyralid, 22+Triclopyr, 22+Flurochloridone, 22+Flurtamone, 22+Diflufenican, 22+Picolinafen, 22+Beflubutamid, 22+Norflurazon, 22+Fluridone.


26+Sulcotrione, 26+Mesotrione, 26+Topramezone, 26+Tembotrione, 26+Bicyclopyrone, 26+Tefuryltrione, 26+Benzobicyclon, 26+Lancotrione, 26+Shuangzuocaotong, 26+Huanbifucaotong, 26+Sanzuohuangcaotong, 26+Benzuofucaotong, 26+Pyrasulfotole, 26+Pyrazolate, 26+Benzofenap, 26+Tolpyralate, 26+Fenquinotrione, 26+Isoxaflutole, 26+Fluroxypyr or esters thereof, 26+Halauxifen-methyl, 26+Florpyrauxifen-benzyl, 26+Quinclorac, 26+Quinmerac, 26+Chipton or salts/esters thereof, 26+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 26+MCPB or salts/esters thereof, 26+2,4-D or salts/esters thereof, 26+Dichlorprop or salts/esters thereof, 26+2,4-DB or salts/esters thereof, 26+Dicamba, 26+Picloram, 26+Trichlopyr, 26+Clopyralid, 26+Triclopyr, 26+Flurochloridone, 26+Flurtamone, 26+Diflufenican, 26+Picolinafen, 26+Beflubutamid, 26+Norflurazon, 26+Fluridone.


27+Sulcotrione, 27+Mesotrione, 27+Topramezone, 27+Tembotrione, 27+Bicyclopyrone, 27+Tefuryltrione, 27+Benzobicyclon, 27+Lancotrione, 27+Shuangzuocaotong, 27+Huanbifucaotong, 27+Sanzuohuangcaotong, 27+Benzuofucaotong, 27+Pyrasulfotole, 27+Pyrazolate, 27+Benzofenap, 27+Tolpyralate, 27+Fenquinotrione, 27+Isoxaflutole, 27+Fluroxypyr or esters thereof, 27+Halauxifen-methyl, 27+Florpyrauxifen-benzyl, 27+Quinclorac, 27+Quinmerac, 27+Chipton or salts/esters thereof, 27+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 27+MCPB or salts/esters thereof, 27+2,4-D or salts/esters thereof, 27+Dichlorprop or salts/esters thereof, 27+2,4-DB or salts/esters thereof, 27+Dicamba, 27+Picloram, 27+Trichlopyr, 27+Clopyralid, 27+Triclopyr, 27+Flurochloridone, 27+Flurtamone, 27+Diflufenican, 27+Picolinafen, 27+Beflubutamid, 27+Norflurazon, 27+Fluridone.


32+Sulcotrione, 32+Mesotrione, 32+Topramezone, 32+Tembotrione, 32+Bicyclopyrone, 32+Tefuryltrione, 32+Benzobicyclon, 32+Lancotrione, 32+Shuangzuocaotong, 32+Huanbifucaotong, 32+Sanzuohuangcaotong, 32+Benzuofucaotong, 32+Pyrasulfotole, 32+Pyrazolate, 32+Benzofenap, 32+Tolpyralate, 32+Fenquinotrione, 32+Isoxaflutole, 32+Fluroxypyr or esters thereof, 32+Halauxifen-methyl, 32+Florpyrauxifen-benzyl, 32+Quinclorac, 32+Quinmerac, 32+Chipton or salts/esters thereof, 32+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 32+MCPB or salts/esters thereof, 32+2,4-D or salts/esters thereof, 32+Dichlorprop or salts/esters thereof, 32+2,4-DB or salts/esters thereof, 32+Dicamba, 32+Picloram, 32+Trichlopyr, 32+Clopyralid, 32+Triclopyr, 32+Flurochloridone, 32+Flurtamone, 32+Diflufenican, 32+Picolinafen, 32+Beflubutamid, 32+Norflurazon, 32+Fluridone.


34+Sulcotrione, 34+Mesotrione, 34+Topramezone, 34+Tembotrione, 34+Bicyclopyrone, 34+Tefuryltrione, 34+Benzobicyclon, 34+Lancotrione, 34+Shuangzuocaotong, 34+Huanbifucaotong, 34+Sanzuohuangcaotong, 34+Benzuofucaotong, 34+Pyrasulfotole, 34+Pyrazolate, 34+Benzofenap, 34+Tolpyralate, 34+Fenquinotrione, 34+Isoxaflutole, 34+Fluroxypyr or esters thereof, 34+Halauxifen-methyl, 34+Florpyrauxifen-benzyl, 34+Quinclorac, 34+Quinmerac, 34+Chipton or salts/esters thereof, 34+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 34+MCPB or salts/esters thereof, 34+2,4-D or salts/esters thereof, 34+Dichlorprop or salts/esters thereof, 34+2,4-DB or salts/esters thereof, 34+Dicamba, 34+Picloram, 34+Trichlopyr, 34+Clopyralid, 34+Triclopyr, 34+Flurochloridone, 34+Flurtamone, 34+Diflufenican, 34+Picolinafen, 34+Beflubutamid, 34+Norflurazon, 34+Fluridone.


35+Sulcotrione, 35+Mesotrione, 35+Topramezone, 35+Tembotrione, 35+Bicyclopyrone, 35+Tefuryltrione, 35+Benzobicyclon, 35+Lancotrione, 35+Shuangzuocaotong, 35+Huanbifucaotong, 35+Sanzuohuangcaotong, 35+Benzuofucaotong, 35+Pyrasulfotole, 35+Pyrazolate, 35+Benzofenap, 35+Tolpyralate, 35+Fenquinotrione, 35+Isoxaflutole, 35+Fluroxypyr or esters thereof, 35+Halauxifen-methyl, 35+Florpyrauxifen-benzyl, 35+Quinclorac, 35+Quinmerac, 35+Chipton or salts/esters thereof, 35+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 35+MCPB or salts/esters thereof, 35+2,4-D or salts/esters thereof, 35+Dichlorprop or salts/esters thereof, 35+2,4-DB or salts/esters thereof, 35+Dicamba, 35+Picloram, 35+Trichlopyr, 35+Clopyralid, 35+Triclopyr, 35+Flurochloridone, 35+Flurtamone, 35+Diflufenican, 35+Picolinafen, 35+Beflubutamid, 35+Norflurazon, 35+Fluridone.


37+Sulcotrione, 37+Mesotrione, 37+Topramezone, 37+Tembotrione, 37+Bicyclopyrone, 37+Tefuryltrione, 37+Benzobicyclon, 37+Lancotrione, 37+Shuangzuocaotong, 37+Huanbifucaotong, 37+Sanzuohuangcaotong, 37+Benzuofucaotong, 37+Pyrasulfotole, 37+Pyrazolate, 37+Benzofenap, 37+Tolpyralate, 37+Fenquinotrione, 37+Isoxaflutole, 37+Fluroxypyr or esters thereof, 37+Halauxifen-methyl, 37+Florpyrauxifen-benzyl, 37+Quinclorac, 37+Quinmerac, 37+Chipton or salts/esters thereof, 37+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 37+MCPB or salts/esters thereof, 37+2,4-D or salts/esters thereof, 37+Dichlorprop or salts/esters thereof, 37+2,4-DB or salts/esters thereof, 37+Dicamba, 37+Picloram, 37+Trichlopyr, 37+Clopyralid, 37+Triclopyr, 37+Flurochloridone, 37+Flurtamone, 37+Diflufenican, 37+Picolinafen, 37+Beflubutamid, 37+Norflurazon, 37+Fluridone.


38+Sulcotrione, 38+Mesotrione, 38+Topramezone, 38+Tembotrione, 38+Bicyclopyrone, 38+Tefuryltrione, 38+Benzobicyclon, 38+Lancotrione, 38+Shuangzuocaotong, 38+Huanbifucaotong, 38+Sanzuohuangcaotong, 38+Benzuofucaotong, 38+Pyrasulfotole, 38+Pyrazolate, 38+Benzofenap, 38+Tolpyralate, 38+Fenquinotrione, 38+Isoxaflutole, 38+Fluroxypyr or esters thereof, 38+Halauxifen-methyl, 38+Florpyrauxifen-benzyl, 38+Quinclorac, 38+Quinmerac, 38+Chipton or salts/esters thereof, 38+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 38+MCPB or salts/esters thereof, 38+2,4-D or salts/esters thereof, 38+Dichlorprop or salts/esters thereof, 38+2,4-DB or salts/esters thereof, 38+Dicamba, 38+Picloram, 38+Trichlopyr, 38+Clopyralid, 38+Triclopyr, 38+Flurochloridone, 38+Flurtamone, 38+Diflufenican, 38+Picolinafen, 38+Beflubutamid, 38+Norflurazon, 38+Fluridone.


39+Sulcotrione, 39+Mesotrione, 39+Topramezone, 39+Tembotrione, 39+Bicyclopyrone, 39+Tefuryltrione, 39+Benzobicyclon, 39+Lancotrione, 39+Shuangzuocaotong, 39+Huanbifucaotong, 39+Sanzuohuangcaotong, 39+Benzuofucaotong, 39+Pyrasulfotole, 39+Pyrazolate, 39+Benzofenap, 39+Tolpyralate, 39+Fenquinotrione, 39+Isoxaflutole, 39+Fluroxypyr or esters thereof, 39+Halauxifen-methyl, 39+Florpyrauxifen-benzyl, 39+Quinclorac, 39+Quinmerac, 39+Chipton or salts/esters thereof, 39+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 39+MCPB or salts/esters thereof, 39+2,4-D or salts/esters thereof, 39+Dichlorprop or salts/esters thereof, 39+2,4-DB or salts/esters thereof, 39+Dicamba, 39+Picloram, 39+Trichlopyr, 39+Clopyralid, 39+Triclopyr, 39+Flurochloridone, 39+Flurtamone, 39+Diflufenican, 39+Picolinafen, 39+Beflubutamid, 39+Norflurazon, 39+Fluridone.


40+Sulcotrione, 40+Mesotrione, 40+Topramezone, 40+Tembotrione, 40+Bicyclopyrone, 40+Tefuryltrione, 40+Benzobicyclon, 40+Lancotrione, 40+Shuangzuocaotong, 40+Huanbifucaotong, 40+Sanzuohuangcaotong, 40+Benzuofucaotong, 40+Pyrasulfotole, 40+Pyrazolate, 40+Benzofenap, 40+Tolpyralate, 40+Fenquinotrione, 40+Isoxaflutole, 40+Fluroxypyr or esters thereof, 40+Halauxifen-methyl, 40+Florpyrauxifen-benzyl, 40+Quinclorac, 40+Quinmerac, 40+Chipton or salts/esters thereof, 40+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 40+MCPB or salts/esters thereof, 40+2,4-D or salts/esters thereof, 40+Dichlorprop or salts/esters thereof, 40+2,4-DB or salts/esters thereof, 40+Dicamba, 40+Picloram, 40+Trichlopyr, 40+Clopyralid, 40+Triclopyr, 40+Flurochloridone, 40+Flurtamone, 40+Diflufenican, 40+Picolinafen, 40+Beflubutamid, 40+Norflurazon, 40+Fluridone.


42+Sulcotrione, 42+Mesotrione, 42+Topramezone, 42+Tembotrione, 42+Bicyclopyrone, 42+Tefuryltrione, 42+Benzobicyclon, 42+Lancotrione, 42+Shuangzuocaotong, 42+Huanbifucaotong, 42+Sanzuohuangcaotong, 42+Benzuofucaotong, 42+Pyrasulfotole, 42+Pyrazolate, 42+Benzofenap, 42+Tolpyralate, 42+Fenquinotrione, 42+Isoxaflutole, 42+Fluroxypyr or esters thereof, 42+Halauxifen-methyl, 42+Florpyrauxifen-benzyl, 42+Quinclorac, 42+Quinmerac, 42+Chipton or salts/esters thereof, 42+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 42+MCPB or salts/esters thereof, 42+2,4-D or salts/esters thereof, 42+Dichlorprop or salts/esters thereof, 42+2,4-DB or salts/esters thereof, 42+Dicamba, 42+Picloram, 42+Trichlopyr, 42+Clopyralid, 42+Triclopyr, 42+Flurochloridone, 42+Flurtamone, 42+Diflufenican, 42+Picolinafen, 42+Beflubutamid, 42+Norflurazon, 42+Fluridone.


43+Sulcotrione, 43+Mesotrione, 43+Topramezone, 43+Tembotrione, 43+Bicyclopyrone, 43+Tefuryltrione, 43+Benzobicyclon, 43+Lancotrione, 43+Shuangzuocaotong, 43+Huanbifucaotong, 43+Sanzuohuangcaotong, 43+Benzuofucaotong, 43+Pyrasulfotole, 43+Pyrazolate, 43+Benzofenap, 43+Tolpyralate, 43+Fenquinotrione, 43+Isoxaflutole, 43+Fluroxypyr or esters thereof, 43+Halauxifen-methyl, 43+Florpyrauxifen-benzyl, 43+Quinclorac, 43+Quinmerac, 43+Chipton or salts/esters thereof, 43+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 43+MCPB or salts/esters thereof, 43+2,4-D or salts/esters thereof, 43+Dichlorprop or salts/esters thereof, 43+2,4-DB or salts/esters thereof, 43+Dicamba, 43+Picloram, 43+Trichlopyr, 43+Clopyralid, 43+Triclopyr, 43+Flurochloridone, 43+Flurtamone, 43+Diflufenican, 43+Picolinafen, 43+Beflubutamid, 43+Norflurazon, 43+Fluridone.


44+Sulcotrione, 44+Mesotrione, 44+Topramezone, 44+Tembotrione, 44+Bicyclopyrone, 44+Tefuryltrione, 44+Benzobicyclon, 44+Lancotrione, 44+Shuangzuocaotong, 44+Huanbifucaotong, 44+Sanzuohuangcaotong, 44+Benzuofucaotong, 44+Pyrasulfotole, 44+Pyrazolate, 44+Benzofenap, 44+Tolpyralate, 44+Fenquinotrione, 44+Isoxaflutole, 44+Fluroxypyr or esters thereof, 44+Halauxifen-methyl, 44+Florpyrauxifen-benzyl, 44+Quinclorac, 44+Quinmerac, 44+Chipton or salts/esters thereof, 44+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 44+MCPB or salts/esters thereof, 44+2,4-D or salts/esters thereof, 44+Dichlorprop or salts/esters thereof, 44+2,4-DB or salts/esters thereof, 44+Dicamba, 44+Picloram, 44+Trichlopyr, 44+Clopyralid, 44+Triclopyr, 44+Flurochloridone, 44+Flurtamone, 44+Diflufenican, 44+Picolinafen, 44+Beflubutamid, 44+Norflurazon, 44+Fluridone.


50+Sulcotrione, 50+Mesotrione, 50+Topramezone, 50+Tembotrione, 50+Bicyclopyrone, 50+Tefuryltrione, 50+Benzobicyclon, 50+Lancotrione, 50+Shuangzuocaotong, 50+Huanbifucaotong, 50+Sanzuohuangcaotong, 50+Benzuofucaotong, 50+Pyrasulfotole, 50+Pyrazolate, 50+Benzofenap, 50+Tolpyralate, 50+Fenquinotrione, 50+Isoxaflutole, 50+Fluroxypyr or esters thereof, 50+Halauxifen-methyl, 50+Florpyrauxifen-benzyl, 50+Quinclorac, 50+Quinmerac, 50+Chipton or salts/esters thereof, 50+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 50+MCPB or salts/esters thereof, 50+2,4-D or salts/esters thereof, 50+Dichlorprop or salts/esters thereof, 50+2,4-DB or salts/esters thereof, 50+Dicamba, 50+Picloram, 50+Trichlopyr, 50+Clopyralid, 50+Triclopyr, 50+Flurochloridone, 50+Flurtamone, 50+Diflufenican, 50+Picolinafen, 50+Beflubutamid, 50+Norflurazon, 50+Fluridone.


51+Sulcotrione, 51+Mesotrione, 51+Topramezone, 51+Tembotrione, 51+Bicyclopyrone, 51+Tefuryltrione, 51+Benzobicyclon, 51+Lancotrione, 51+Shuangzuocaotong, 51+Huanbifucaotong, 51+Sanzuohuangcaotong, 51+Benzuofucaotong, 51+Pyrasulfotole, 51+Pyrazolate, 51+Benzofenap, 51+Tolpyralate, 51+Fenquinotrione, 51+Isoxaflutole, 51+Fluroxypyr or esters thereof, 51+Halauxifen-methyl, 51+Florpyrauxifen-benzyl, 51+Quinclorac, 51+Quinmerac, 51+Chipton or salts/esters thereof, 51+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 51+MCPB or salts/esters thereof, 51+2,4-D or salts/esters thereof, 51+Dichlorprop or salts/esters thereof, 51+2,4-DB or salts/esters thereof, 51+Dicamba, 51+Picloram, 51+Trichlopyr, 51+Clopyralid, 51+Triclopyr, 51+Flurochloridone, 51+Flurtamone, 51+Diflufenican, 51+Picolinafen, 51+Beflubutamid, 51+Norflurazon, 51+Fluridone.


53+Sulcotrione, 53+Mesotrione, 53+Topramezone, 53+Tembotrione, 53+Bicyclopyrone, 53+Tefuryltrione, 53+Benzobicyclon, 53+Lancotrione, 53+Shuangzuocaotong, 53+Huanbifucaotong, 53+Sanzuohuangcaotong, 53+Benzuofucaotong, 53+Pyrasulfotole, 53+Pyrazolate, 53+Benzofenap, 53+Tolpyralate, 53+Fenquinotrione, 53+Isoxaflutole, 53+Fluroxypyr or esters thereof, 53+Halauxifen-methyl, 53+Florpyrauxifen-benzyl, 53+Quinclorac, 53+Quinmerac, 53+Chipton or salts/esters thereof, 53+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 53+MCPB or salts/esters thereof, 53+2,4-D or salts/esters thereof, 53+Dichlorprop or salts/esters thereof, 53+2,4-DB or salts/esters thereof, 53+Dicamba, 53+Picloram, 53+Trichlopyr, 53+Clopyralid, 53+Triclopyr, 53+Flurochloridone, 53+Flurtamone, 53+Diflufenican, 53+Picolinafen, 53+Beflubutamid, 53+Norflurazon, 53+Fluridone.


56+Sulcotrione, 56+Mesotrione, 56+Topramezone, 56+Tembotrione, 56+Bicyclopyrone, 56+Tefuryltrione, 56+Benzobicyclon, 56+Lancotrione, 56+Shuangzuocaotong, 56+Huanbifucaotong, 56+Sanzuohuangcaotong, 56+Benzuofucaotong, 56+Pyrasulfotole, 56+Pyrazolate, 56+Benzofenap, 56+Tolpyralate, 56+Fenquinotrione, 56+Isoxaflutole, 56+Fluroxypyr or esters thereof, 56+Halauxifen-methyl, 56+Florpyrauxifen-benzyl, 56+Quinclorac, 56+Quinmerac, 56+Chipton or salts/esters thereof, 56+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 56+MCPB or salts/esters thereof, 56+2,4-D or salts/esters thereof, 56+Dichlorprop or salts/esters thereof, 56+2,4-DB or salts/esters thereof, 56+Dicamba, 56+Picloram, 56+Trichlopyr, 56+Clopyralid, 56+Triclopyr, 56+Flurochloridone, 56+Flurtamone, 56+Diflufenican, 56+Picolinafen, 56+Beflubutamid, 56+Norflurazon, 56+Fluridone.


57+Sulcotrione, 57+Mesotrione, 57+Topramezone, 57+Tembotrione, 57+Bicyclopyrone, 57+Tefuryltrione, 57+Benzobicyclon, 57+Lancotrione, 57+Shuangzuocaotong, 57+Huanbifucaotong, 57+Sanzuohuangcaotong, 57+Benzuofucaotong, 57+Pyrasulfotole, 57+Pyrazolate, 57+Benzofenap, 57+Tolpyralate, 57+Fenquinotrione, 57+Isoxaflutole, 57+Fluroxypyr or esters thereof, 57+Halauxifen-methyl, 57+Florpyrauxifen-benzyl, 57+Quinclorac, 57+Quinmerac, 57+Chipton or salts/esters thereof, 57+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 57+MCPB or salts/esters thereof, 57+2,4-D or salts/esters thereof, 57+Dichlorprop or salts/esters thereof, 57+2,4-DB or salts/esters thereof, 57+Dicamba, 57+Picloram, 57+Trichlopyr, 57+Clopyralid, 57+Triclopyr, 57+Flurochloridone, 57+Flurtamone, 57+Diflufenican, 57+Picolinafen, 57+Beflubutamid, 57+Norflurazon, 57+Fluridone.


58+Sulcotrione, 58+Mesotrione, 58+Topramezone, 58+Tembotrione, 58+Bicyclopyrone, 58+Tefuryltrione, 58+Benzobicyclon, 58+Lancotrione, 58+Shuangzuocaotong, 58+Huanbifucaotong, 58+Sanzuohuangcaotong, 58+Benzuofucaotong, 58+Pyrasulfotole, 58+Pyrazolate, 58+Benzofenap, 58+Tolpyralate, 58+Fenquinotrione, 58+Isoxaflutole, 58+Fluroxypyr or esters thereof, 58+Halauxifen-methyl, 58+Florpyrauxifen-benzyl, 58+Quinclorac, 58+Quinmerac, 58+Chipton or salts/esters thereof, 58+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 58+MCPB or salts/esters thereof, 58+2,4-D or salts/esters thereof, 58+Dichlorprop or salts/esters thereof, 58+2,4-DB or salts/esters thereof, 58+Dicamba, 58+Picloram, 58+Trichlopyr, 58+Clopyralid, 58+Triclopyr, 58+Flurochloridone, 58+Flurtamone, 58+Diflufenican, 58+Picolinafen, 58+Beflubutamid, 58+Norflurazon, 58+Fluridone.


59+Sulcotrione, 59+Mesotrione, 59+Topramezone, 59+Tembotrione, 59+Bicyclopyrone, 59+Tefuryltrione, 59+Benzobicyclon, 59+Lancotrione, 59+Shuangzuocaotong, 59+Huanbifucaotong, 59+Sanzuohuangcaotong, 59+Benzuofucaotong, 59+Pyrasulfotole, 59+Pyrazolate, 59+Benzofenap, 59+Tolpyralate, 59+Fenquinotrione, 59+Isoxaflutole, 59+Fluroxypyr or esters thereof, 59+Halauxifen-methyl, 59+Florpyrauxifen-benzyl, 59+Quinclorac, 59+Quinmerac, 59+Chipton or salts/esters thereof, 59+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 59+MCPB or salts/esters thereof, 59+2,4-D or salts/esters thereof, 59+Dichlorprop or salts/esters thereof, 59+2,4-DB or salts/esters thereof, 59+Dicamba, 59+Picloram, 59+Trichlopyr, 59+Clopyralid, 59+Triclopyr, 59+Flurochloridone, 59+Flurtamone, 59+Diflufenican, 59+Picolinafen, 59+Beflubutamid, 59+Norflurazon, 59+Fluridone.


60+Sulcotrione, 60+Mesotrione, 60+Topramezone, 60+Tembotrione, 60+Bicyclopyrone, 60+Tefuryltrione, 60+Benzobicyclon, 60+Lancotrione, 60+Shuangzuocaotong, 60+Huanbifucaotong, 60+Sanzuohuangcaotong, 60+Benzuofucaotong, 60+Pyrasulfotole, 60+Pyrazolate, 60+Benzofenap, 60+Tolpyralate, 60+Fenquinotrione, 60+Isoxaflutole, 60+Fluroxypyr or esters thereof, 60+Halauxifen-methyl, 60+Florpyrauxifen-benzyl, 60+Quinclorac, 60+Quinmerac, 60+Chipton or salts/esters thereof, 60+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 60+MCPB or salts/esters thereof, 60+2,4-D or salts/esters thereof, 60+Dichlorprop or salts/esters thereof, 60+2,4-DB or salts/esters thereof, 60+Dicamba, 60+Picloram, 60+Trichlopyr, 60+Clopyralid, 60+Triclopyr, 60+Flurochloridone, 60+Flurtamone, 60+Diflufenican, 60+Picolinafen, 60+Beflubutamid, 60+Norflurazon, 60+Fluridone.


66+Sulcotrione, 66+Mesotrione, 66+Topramezone, 66+Tembotrione, 66+Bicyclopyrone, 66+Tefuryltrione, 66+Benzobicyclon, 66+Lancotrione, 66+Shuangzuocaotong, 66+Huanbifucaotong, 66+Sanzuohuangcaotong, 66+Benzuofucaotong, 66+Pyrasulfotole, 66+Pyrazolate, 66+Benzofenap, 66+Tolpyralate, 66+Fenquinotrione, 66+Isoxaflutole, 66+Fluroxypyr or esters thereof, 66+Halauxifen-methyl, 66+Florpyrauxifen-benzyl, 66+Quinclorac, 66+Quinmerac, 66+Chipton or salts/esters thereof, 66+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 66+MCPB or salts/esters thereof, 66+2,4-D or salts/esters thereof, 66+Dichlorprop or salts/esters thereof, 66+2,4-DB or salts/esters thereof, 66+Dicamba, 66+Picloram, 66+Trichlopyr, 66+Clopyralid, 66+Triclopyr, 66+Flurochloridone, 66+Flurtamone, 66+Diflufenican, 66+Picolinafen, 66+Beflubutamid, 66+Norflurazon, 66+Fluridone.


68+Sulcotrione, 68+Mesotrione, 68+Topramezone, 68+Tembotrione, 68+Bicyclopyrone, 68+Tefuryltrione, 68+Benzobicyclon, 68+Lancotrione, 68+Shuangzuocaotong, 68+Huanbifucaotong, 68+Sanzuohuangcaotong, 68+Benzuofucaotong, 68+Pyrasulfotole, 68+Pyrazolate, 68+Benzofenap, 68+Tolpyralate, 68+Fenquinotrione, 68+Isoxaflutole, 68+Fluroxypyr or esters thereof, 68+Halauxifen-methyl, 68+Florpyrauxifen-benzyl, 68+Quinclorac, 68+Quinmerac, 68+Chipton or salts/esters thereof, 68+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 68+MCPB or salts/esters thereof, 68+2,4-D or salts/esters thereof, 68+Dichlorprop or salts/esters thereof, 68+2,4-DB or salts/esters thereof, 68+Dicamba, 68+Picloram, 68+Trichlopyr, 68+Clopyralid, 68+Triclopyr, 68+Flurochloridone, 68+Flurtamone, 68+Diflufenican, 68+Picolinafen, 68+Beflubutamid, 68+Norflurazon, 68+Fluridone.


77+Sulcotrione, 77+Mesotrione, 77+Topramezone, 77+Tembotrione, 77+Bicyclopyrone, 77+Tefuryltrione, 77+Benzobicyclon, 77+Lancotrione, 77+Shuangzuocaotong, 77+Huanbifucaotong, 77+Sanzuohuangcaotong, 77+Benzuofucaotong, 77+Pyrasulfotole, 77+Pyrazolate, 77+Benzofenap, 77+Tolpyralate, 77+Fenquinotrione, 77+Isoxaflutole, 77+Fluroxypyr or esters thereof, 77+Halauxifen-methyl, 77+Florpyrauxifen-benzyl, 77+Quinclorac, 77+Quinmerac, 77+Chipton or salts/esters thereof, 77+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 77+MCPB or salts/esters thereof, 77+2,4-D or salts/esters thereof, 77+Dichlorprop or salts/esters thereof, 77+2,4-DB or salts/esters thereof, 77+Dicamba, 77+Picloram, 77+Trichlopyr, 77+Clopyralid, 77+Triclopyr, 77+Flurochloridone, 77+Flurtamone, 77+Diflufenican, 77+Picolinafen, 77+Beflubutamid, 77+Norflurazon, 77+Fluridone.


79+Sulcotrione, 79+Mesotrione, 79+Topramezone, 79+Tembotrione, 79+Bicyclopyrone, 79+Tefuryltrione, 79+Benzobicyclon, 79+Lancotrione, 79+Shuangzuocaotong, 79+Huanbifucaotong, 79+Sanzuohuangcaotong, 79+Benzuofucaotong, 79+Pyrasulfotole, 79+Pyrazolate, 79+Benzofenap, 79+Tolpyralate, 79+Fenquinotrione, 79+Isoxaflutole, 79+Fluroxypyr or esters thereof, 79+Halauxifen-methyl, 79+Florpyrauxifen-benzyl, 79+Quinclorac, 79+Quinmerac, 79+Chipton or salts/esters thereof, 79+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 79+MCPB or salts/esters thereof, 79+2,4-D or salts/esters thereof, 79+Dichlorprop or salts/esters thereof, 79+2,4-DB or salts/esters thereof, 79+Dicamba, 79+Picloram, 79+Trichlopyr, 79+Clopyralid, 79+Triclopyr, 79+Flurochloridone, 79+Flurtamone, 79+Diflufenican, 79+Picolinafen, 79+Beflubutamid, 79+Norflurazon, 79+Fluridone.


87+Sulcotrione, 87+Mesotrione, 87+Topramezone, 87+Tembotrione, 87+Bicyclopyrone, 87+Tefuryltrione, 87+Benzobicyclon, 87+Lancotrione, 87+Shuangzuocaotong, 87+Huanbifucaotong, 87+Sanzuohuangcaotong, 87+Benzuofucaotong, 87+Pyrasulfotole, 87+Pyrazolate, 87+Benzofenap, 87+Tolpyralate, 87+Fenquinotrione, 87+Isoxaflutole, 87+Fluroxypyr or esters thereof, 87+Halauxifen-methyl, 87+Florpyrauxifen-benzyl, 87+Quinclorac, 87+Quinmerac, 87+Chipton or salts/esters thereof, 87+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 87+MCPB or salts/esters thereof, 87+2,4-D or salts/esters thereof, 87+Dichlorprop or salts/esters thereof, 87+2,4-DB or salts/esters thereof, 87+Dicamba, 87+Picloram, 87+Trichlopyr, 87+Clopyralid, 87+Triclopyr, 87+Flurochloridone, 87+Flurtamone, 87+Diflufenican, 87+Picolinafen, 87+Beflubutamid, 87+Norflurazon, 87+Fluridone.


92+Sulcotrione, 92+Mesotrione, 92+Topramezone, 92+Tembotrione, 92+Bicyclopyrone, 92+Tefuryltrione, 92+Benzobicyclon, 92+Lancotrione, 92+Shuangzuocaotong, 92+Huanbifucaotong, 92+Sanzuohuangcaotong, 92+Benzuofucaotong, 92+Pyrasulfotole, 92+Pyrazolate, 92+Benzofenap, 92+Tolpyralate, 92+Fenquinotrione, 92+Isoxaflutole, 92+Fluroxypyr or esters thereof, 92+Halauxifen-methyl, 92+Florpyrauxifen-benzyl, 92+Quinclorac, 92+Quinmerac, 92+Chipton or salts/esters thereof, 92+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 92+MCPB or salts/esters thereof, 92+2,4-D or salts/esters thereof, 92+Dichlorprop or salts/esters thereof, 92+2,4-DB or salts/esters thereof, 92+Dicamba, 92+Picloram, 92+Trichlopyr, 92+Clopyralid, 92+Triclopyr, 92+Flurochloridone, 92+Flurtamone, 92+Diflufenican, 92+Picolinafen, 92+Beflubutamid, 92+Norflurazon, 92+Fluridone. 191+Sulcotrione, 191+Mesotrione, 191+Topramezone, 191+Tembotrione, 191+Bicyclopyrone, 191+Tefuryltrione, 191+Benzobicyclon, 191+Lancotrione, 191+Shuangzuocaotong, 191+Huanbifucaotong, 191+Sanzuohuangcaotong, 191+Benzuofucaotong,


191+Pyrasulfotole, 191+Pyrazolate, 191+Benzofenap, 191+Tolpyralate, 191+Fenquinotrione, 191+Isoxaflutole, 191+Fluroxypyr or esters thereof, 191+Halauxifen-methyl, 191+Florpyrauxifen-benzyl, 191+Quinclorac, 191+Quinmerac, 191+Chipton or salts/esters thereof, 191+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 191+MCPB or salts/esters thereof, 191+2,4-D or salts/esters thereof, 191+Dichlorprop or salts/esters thereof, 191+2,4-DB or salts/esters thereof, 191+Dicamba, 191+Picloram, 191+Trichlopyr, 191+Clopyralid, 191+Triclopyr, 191+Flurochloridone, 191+Flurtamone, 191+Diflufenican, 191+Picolinafen, 191+Beflubutamid, 191+Norflurazon, 191+Fluridone.


202+Sulcotrione, 202+Mesotrione, 202+Topramezone, 202+Tembotrione, 202+Bicyclopyrone, 202+Tefuryltrione, 202+Benzobicyclon, 202+Lancotrione, 202+Shuangzuocaotong, 202+Huanbifucaotong, 202+Sanzuohuangcaotong, 202+Benzuofucaotong, 202+Pyrasulfotole, 202+Pyrazolate, 202+Benzofenap, 202+Tolpyralate, 202+Fenquinotrione, 202+Isoxaflutole, 202+Fluroxypyr or esters thereof, 202+Halauxifen-methyl, 202+Florpyrauxifen-benzyl, 202+Quinclorac, 202+Quinmerac, 202+Chipton or salts/esters thereof, 202+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 202+MCPB or salts/esters thereof, 202+2,4-D or salts/esters thereof, 202+Dichlorprop or salts/esters thereof, 202+2,4-DB or salts/esters thereof, 202+Dicamba, 202+Picloram, 202+Trichlopyr, 202+Clopyralid, 202+Triclopyr, 202+Flurochloridone, 202+Flurtamone, 202+Diflufenican, 202+Picolinafen, 202+Beflubutamid, 202+Norflurazon, 202+Fluridone.


206+Sulcotrione, 206+Mesotrione, 206+Topramezone, 206+Tembotrione, 206+Bicyclopyrone, 206+Tefuryltrione, 206+Benzobicyclon, 206+Lancotrione, 206+Shuangzuocaotong, 206+Huanbifucaotong, 206+Sanzuohuangcaotong, 206+Benzuofucaotong, 206+Pyrasulfotole, 206+Pyrazolate, 206+Benzofenap, 206+Tolpyralate, 206+Fenquinotrione, 206+Isoxaflutole, 206+Fluroxypyr or esters thereof, 206+Halauxifen-methyl, 206+Florpyrauxifen-benzyl, 206+Quinclorac, 206+Quinmerac, 206+Chipton or salts/esters thereof, 206+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 206+MCPB or salts/esters thereof, 206+2,4-D or salts/esters thereof, 206+Dichlorprop or salts/esters thereof, 206+2,4-DB or salts/esters thereof, 206+Dicamba, 206+Picloram, 206+Trichlopyr, 206+Clopyralid, 206+Triclopyr, 206+Flurochloridone, 206+Flurtamone, 206+Diflufenican, 206+Picolinafen, 206+Beflubutamid, 206+Norflurazon, 206+Fluridone. 207+Sulcotrione, 207+Mesotrione, 207+Topramezone, 207+Tembotrione, 207+Bicyclopyrone, 207+Tefuryltrione, 207+Benzobicyclon, 207+Lancotrione, 207+Shuangzuocaotong, 207+Huanbifucaotong, 207+Sanzuohuangcaotong, 207+Benzuofucaotong,


207+Pyrasulfotole, 207+Pyrazolate, 207+Benzofenap, 207+Tolpyralate, 207+Fenquinotrione, 207+Isoxaflutole, 207+Fluroxypyr or esters thereof, 207+Halauxifen-methyl, 207+Florpyrauxifen-benzyl, 207+Quinclorac, 207+Quinmerac, 207+Chipton or salts/esters thereof, 207+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 207+MCPB or salts/esters thereof, 207+2,4-D or salts/esters thereof, 207+Dichlorprop or salts/esters thereof, 207+2,4-DB or salts/esters thereof, 207+Dicamba, 207+Picloram, 207+Trichlopyr, 207+Clopyralid, 207+Triclopyr, 207+Flurochloridone, 207+Flurtamone, 207+Diflufenican, 207+Picolinafen, 207+Beflubutamid, 207+Norflurazon, 207+Fluridone.


220+Sulcotrione, 220+Mesotrione, 220+Topramezone, 220+Tembotrione, 220+Bicyclopyrone, 220+Tefuryltrione, 220+Benzobicyclon, 220+Lancotrione, 220+Shuangzuocaotong, 220+Huanbifucaotong, 220+Sanzuohuangcaotong, 220+Benzuofucaotong, 220+Pyrasulfotole, 220+Pyrazolate, 220+Benzofenap, 220+Tolpyralate, 220+Fenquinotrione, 220+Isoxaflutole, 220+Fluroxypyr or esters thereof, 220+Halauxifen-methyl, 220+Florpyrauxifen-benzyl, 220+Quinclorac, 220+Quinmerac, 220+Chipton or salts/esters thereof, 220+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 220+MCPB or salts/esters thereof, 220+2,4-D or salts/esters thereof, 220+Dichlorprop or salts/esters thereof, 220+2,4-DB or salts/esters thereof, 220+Dicamba, 220+Picloram, 220+Trichlopyr, 220+Clopyralid, 220+Triclopyr, 220+Flurochloridone, 220+Flurtamone, 220+Diflufenican, 220+Picolinafen, 220+Beflubutamid, 220+Norflurazon, 220+Fluridone.


278+Sulcotrione, 278+Mesotrione, 278+Topramezone, 278+Tembotrione, 278+Bicyclopyrone, 278+Tefuryltrione, 278+Benzobicyclon, 278+Lancotrione, 278+Shuangzuocaotong, 278+Huanbifucaotong, 278+Sanzuohuangcaotong, 278+Benzuofucaotong, 278+Pyrasulfotole, 278+Pyrazolate, 278+Benzofenap, 278+Tolpyralate, 278+Fenquinotrione, 278+Isoxaflutole, 278+Fluroxypyr or esters thereof, 278+Halauxifen-methyl, 278+Florpyrauxifen-benzyl, 278+Quinclorac, 278+Quinmerac, 278+Chipton or salts/esters thereof, 278+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 278+MCPB or salts/esters thereof, 278+2,4-D or salts/esters thereof, 278+Dichlorprop or salts/esters thereof, 278+2,4-DB or salts/esters thereof, 278+Dicamba, 278+Picloram, 278+Trichlopyr, 278+Clopyralid, 278+Triclopyr, 278+Flurochloridone, 278+Flurtamone, 278+Diflufenican, 278+Picolinafen, 278+Beflubutamid, 278+Norflurazon, 278+Fluridone.


341+Sulcotrione, 341+Mesotrione, 341+Topramezone, 341+Tembotrione, 341+Bicyclopyrone, 341+Tefuryltrione, 341+Benzobicyclon, 341+Lancotrione, 341+Shuangzuocaotong, 341+Huanbifucaotong, 341+Sanzuohuangcaotong, 341+Benzuofucaotong, 341+Pyrasulfotole, 341+Pyrazolate, 341+Benzofenap, 341+Tolpyralate, 341+Fenquinotrione, 341+Isoxaflutole, 341+Fluroxypyr or esters thereof, 341+Halauxifen-methyl, 341+Florpyrauxifen-benzyl, 341+Quinclorac, 341+Quinmerac, 341+Chipton or salts/esters thereof, 341+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 341+MCPB or salts/esters thereof, 341+2,4-D or salts/esters thereof, 341+Dichlorprop or salts/esters thereof, 341+2,4-DB or salts/esters thereof, 341+Dicamba, 341+Picloram, 341+Trichlopyr, 341+Clopyralid, 341+Triclopyr, 341+Flurochloridone, 341+Flurtamone, 341+Diflufenican, 341+Picolinafen, 341+Beflubutamid, 341+Norflurazon, 341+Fluridone.


732+Sulcotrione, 732+Mesotrione, 732+Topramezone, 732+Tembotrione, 732+Bicyclopyrone, 732+Tefuryltrione, 732+Benzobicyclon, 732+Lancotrione, 732+Shuangzuocaotong, 732+Huanbifucaotong, 732+Sanzuohuangcaotong, 732+Benzuofucaotong, 732+Pyrasulfotole, 732+Pyrazolate, 732+Benzofenap, 732+Tolpyralate, 732+Fenquinotrione, 732+Isoxaflutole, 732+Fluroxypyr or esters thereof, 732+Halauxifen-methyl, 732+Florpyrauxifen-benzyl, 732+Quinclorac, 732+Quinmerac, 732+Chipton or salts/esters thereof, 732+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 732+MCPB or salts/esters thereof, 732+2,4-D or salts/esters thereof, 732+Dichlorprop or salts/esters thereof, 732+2,4-DB or salts/esters thereof, 732+Dicamba, 732+Picloram, 732+Trichlopyr, 732+Clopyralid, 732+Triclopyr, 732+Flurochloridone, 732+Flurtamone, 732+Diflufenican, 732+Picolinafen, 732+Beflubutamid, 732+Norflurazon, 732+Fluridone.


733+Sulcotrione, 733+Mesotrione, 733+Topramezone, 733+Tembotrione, 733+Bicyclopyrone, 733+Tefuryltrione, 733+Benzobicyclon, 733+Lancotrione, 733+Shuangzuocaotong, 733+Huanbifucaotong, 733+Sanzuohuangcaotong, 733+Benzuofucaotong, 733+Pyrasulfotole, 733+Pyrazolate, 733+Benzofenap, 733+Tolpyralate, 733+Fenquinotrione, 733+Isoxaflutole, 733+Fluroxypyr or esters thereof, 733+Halauxifen-methyl, 733+Florpyrauxifen-benzyl, 733+Quinclorac, 733+Quinmerac, 733+Chipton or salts/esters thereof, 733+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 733+MCPB or salts/esters thereof, 733+2,4-D or salts/esters thereof, 733+Dichlorprop or salts/esters thereof, 733+2,4-DB or salts/esters thereof, 733+Dicamba, 733+Picloram, 733+Trichlopyr, 733+Clopyralid, 733+Triclopyr, 733+Flurochloridone, 733+Flurtamone, 733+Diflufenican, 733+Picolinafen, 733+Beflubutamid, 733+Norflurazon, 733+Fluridone.


734+Sulcotrione, 734+Mesotrione, 734+Topramezone, 734+Tembotrione, 734+Bicyclopyrone, 734+Tefuryltrione, 734+Benzobicyclon, 734+Lancotrione, 734+Shuangzuocaotong, 734+Huanbifucaotong, 734+Sanzuohuangcaotong, 734+Benzuofucaotong, 734+Pyrasulfotole, 734+Pyrazolate, 734+Benzofenap, 734+Tolpyralate, 734+Fenquinotrione, 734+Isoxaflutole, 734+Fluroxypyr or esters thereof, 734+Halauxifen-methyl, 734+Florpyrauxifen-benzyl, 734+Quinclorac, 734+Quinmerac, 734+Chipton or salts/esters thereof, 734+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 734+MCPB or salts/esters thereof, 734+2,4-D or salts/esters thereof, 734+Dichlorprop or salts/esters thereof, 734+2,4-DB or salts/esters thereof, 734+Dicamba, 734+Picloram, 734+Trichlopyr, 734+Clopyralid, 734+Triclopyr, 734+Flurochloridone, 734+Flurtamone, 734+Diflufenican, 734+Picolinafen, 734+Beflubutamid, 734+Norflurazon, 734+Fluridone.


735+Sulcotrione, 735+Mesotrione, 735+Topramezone, 735+Tembotrione, 735+Bicyclopyrone, 735+Tefuryltrione, 735+Benzobicyclon, 735+Lancotrione, 735+Shuangzuocaotong, 735+Huanbifucaotong, 735+Sanzuohuangcaotong, 735+Benzuofucaotong, 735+Pyrasulfotole, 735+Pyrazolate, 735+Benzofenap, 735+Tolpyralate, 735+Fenquinotrione, 735+Isoxaflutole, 735+Fluroxypyr or esters thereof, 735+Halauxifen-methyl, 735+Florpyrauxifen-benzyl, 735+Quinclorac, 735+Quinmerac, 735+Chipton or salts/esters thereof, 735+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 735+MCPB or salts/esters thereof, 735+2,4-D or salts/esters thereof, 735+Dichlorprop or salts/esters thereof, 735+2,4-DB or salts/esters thereof, 735+Dicamba, 735+Picloram, 735+Trichlopyr, 735+Clopyralid, 735+Triclopyr, 735+Flurochloridone, 735+Flurtamone, 735+Diflufenican, 735+Picolinafen, 735+Beflubutamid, 735+Norflurazon, 735+Fluridone. 736+Sulcotrione, 736+Mesotrione, 736+Topramezone, 736+Tembotrione, 736+Bicyclopyrone, 736+Tefuryltrione, 736+Benzobicyclon, 736+Lancotrione, 736+Shuangzuocaotong, 736+Huanbifucaotong, 736+Sanzuohuangcaotong, 736+Benzuofucaotong,


736+Pyrasulfotole, 736+Pyrazolate, 736+Benzofenap, 736+Tolpyralate, 736+Fenquinotrione, 736+Isoxaflutole, 736+Fluroxypyr or esters thereof, 736+Halauxifen-methyl, 736+Florpyrauxifen-benzyl, 736+Quinclorac, 736+Quinmerac, 736+Chipton or salts/esters thereof, 736+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 736+MCPB or salts/esters thereof, 736+2,4-D or salts/esters thereof, 736+Dichlorprop or salts/esters thereof, 736+2,4-DB or salts/esters thereof, 736+Dicamba, 736+Picloram, 736+Trichlopyr, 736+Clopyralid, 736+Triclopyr, 736+Flurochloridone, 736+Flurtamone, 736+Diflufenican, 736+Picolinafen, 736+Beflubutamid, 736+Norflurazon, 736+Fluridone.


737+Sulcotrione, 737+Mesotrione, 737+Topramezone, 737+Tembotrione, 737+Bicyclopyrone, 737+Tefuryltrione, 737+Benzobicyclon, 737+Lancotrione, 737+Shuangzuocaotong, 737+Huanbifucaotong, 737+Sanzuohuangcaotong, 737+Benzuofucaotong, 737+Pyrasulfotole, 737+Pyrazolate, 737+Benzofenap, 737+Tolpyralate, 737+Fenquinotrione, 737+Isoxaflutole, 737+Fluroxypyr or esters thereof, 737+Halauxifen-methyl, 737+Florpyrauxifen-benzyl, 737+Quinclorac, 737+Quinmerac, 737+Chipton or salts/esters thereof, 737+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 737+MCPB or salts/esters thereof, 737+2,4-D or salts/esters thereof, 737+Dichlorprop or salts/esters thereof, 737+2,4-DB or salts/esters thereof, 737+Dicamba, 737+Picloram, 737+Trichlopyr, 737+Clopyralid, 737+Triclopyr, 737+Flurochloridone, 737+Flurtamone, 737+Diflufenican, 737+Picolinafen, 737+Beflubutamid, 737+Norflurazon, 737+Fluridone.


738+Sulcotrione, 738+Mesotrione, 738+Topramezone, 738+Tembotrione, 738+Bicyclopyrone, 738+Tefuryltrione, 738+Benzobicyclon, 738+Lancotrione, 738+Shuangzuocaotong, 738+Huanbifucaotong, 738+Sanzuohuangcaotong, 738+Benzuofucaotong, 738+Pyrasulfotole, 738+Pyrazolate, 738+Benzofenap, 738+Tolpyralate, 738+Fenquinotrione, 738+Isoxaflutole, 738+Fluroxypyr or esters thereof, 738+Halauxifen-methyl, 738+Florpyrauxifen-benzyl, 738+Quinclorac, 738+Quinmerac, 738+Chipton or salts/esters thereof, 738+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 738+MCPB or salts/esters thereof, 738+2,4-D or salts/esters thereof, 738+Dichlorprop or salts/esters thereof, 738+2,4-DB or salts/esters thereof, 738+Dicamba, 738+Picloram, 738+Trichlopyr, 738+Clopyralid, 738+Triclopyr, 738+Flurochloridone, 738+Flurtamone, 738+Diflufenican, 738+Picolinafen, 738+Beflubutamid, 738+Norflurazon, 738+Fluridone.


739+Sulcotrione, 739+Mesotrione, 739+Topramezone, 739+Tembotrione, 739+Bicyclopyrone, 739+Tefuryltrione, 739+Benzobicyclon, 739+Lancotrione, 739+Shuangzuocaotong, 739+Huanbifucaotong, 739+S anzuohuangc aotong, 739+Benzuofucaotong, 739+Pyrasulfotole, 739+Pyrazolate, 739+Benzofenap, 739+Tolpyralate, 739+Fenquinotrione, 739+Isoxaflutole, 739+Fluroxypyr or esters thereof, 739+Halauxifen-methyl, 739+Florpyrauxifen-benzyl, 739+Quinclorac, 739+Quinmerac, 739+Chipton or salts/esters thereof, 739+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 739+MCPB or salts/esters thereof, 739+2,4-D or salts/esters thereof, 739+Dichlorprop or salts/esters thereof, 739+2,4-DB or salts/esters thereof, 739+Dicamba, 739+Picloram, 739+Trichlopyr, 739+Clopyralid, 739+Triclopyr, 739+Flurochloridone, 739+Flurtamone, 739+Diflufenican, 739+Picolinafen, 739+Beflubutamid, 739+Norflurazon, 739+Fluridone.


740+Sulcotrione, 740+Mesotrione, 740+Topramezone, 740+Tembotrione, 740+Bicyclopyrone, 740+Tefuryltrione, 740+Benzobicyclon, 740+Lancotrione, 740+Shuangzuocaotong, 740+Huanbifucaotong, 740+Sanzuohuangcaotong, 740+Benzuofucaotong, 740+Pyrasulfotole, 740+Pyrazolate, 740+Benzofenap, 740+Tolpyralate, 740+Fenquinotrione, 740+Isoxaflutole, 740+Fluroxypyr or esters thereof, 740+Halauxifen-methyl, 740+Florpyrauxifen-benzyl, 740+Quinclorac, 740+Quinmerac, 740+Chipton or salts/esters thereof, 740+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 740+MCPB or salts/esters thereof, 740+2,4-D or salts/esters thereof, 740+Dichlorprop or salts/esters thereof, 740+2,4-DB or salts/esters thereof, 740+Dicamba, 740+Picloram, 740+Trichlopyr, 740+Clopyralid, 740+Triclopyr, 740+Flurochloridone, 740+Flurtamone, 740+Diflufenican, 740+Picolinafen, 740+Beflubutamid, 740+Norflurazon, 740+Fluridone.


741+Sulcotrione, 741+Mesotrione, 741+Topramezone, 741+Tembotrione, 741+Bicyclopyrone, 741+Tefuryltrione, 741+Benzobicyclon, 741+Lancotrione, 741+Shuangzuocaotong, 741+Huanbifucaotong, 741+Sanzuohuangcaotong, 741+Benzuofucaotong, 741+Pyrasulfotole, 741+Pyrazolate, 741+Benzofenap, 741+Tolpyralate, 741+Fenquinotrione, 741+Isoxaflutole, 741+Fluroxypyr or esters thereof, 741+Halauxifen-methyl, 741+Florpyrauxifen-benzyl, 741+Quinclorac, 741+Quinmerac, 741+Chipton or salts/esters thereof, 741+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 741+MCPB or salts/esters thereof, 741+2,4-D or salts/esters thereof, 741+Dichlorprop or salts/esters thereof, 741+2,4-DB or salts/esters thereof, 741+Dicamba, 741+Picloram, 741+Trichlopyr, 741+Clopyralid, 741+Triclopyr, 741+Flurochloridone, 741+Flurtamone, 741+Diflufenican, 741+Picolinafen, 741+Beflubutamid, 741+Norflurazon, 741+Fluridone.


742+Sulcotrione, 742+Mesotrione, 742+Topramezone, 742+Tembotrione, 742+Bicyclopyrone, 742+Tefuryltrione, 742+Benzobicyclon, 742+Lancotrione, 742+Shuangzuocaotong, 742+Huanbifucaotong, 742+Sanzuohuangcaotong, 742+Benzuofucaotong, 742+Pyrasulfotole, 742+Pyrazolate, 742+Benzofenap, 742+Tolpyralate, 742+Fenquinotrione, 742+Isoxaflutole, 742+Fluroxypyr or esters thereof, 742+Halauxifen-methyl, 742+Florpyrauxifen-benzyl, 742+Quinclorac, 742+Quinmerac, 742+Chipton or salts/esters thereof, 742+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 742+MCPB or salts/esters thereof, 742+2,4-D or salts/esters thereof, 742+Dichlorprop or salts/esters thereof, 742+2,4-DB or salts/esters thereof, 742+Dicamba, 742+Picloram, 742+Trichlopyr, 742+Clopyralid, 742+Triclopyr, 742+Flurochloridone, 742+Flurtamone, 742+Diflufenican, 742+Picolinafen, 742+Beflubutamid, 742+Norflurazon, 742+Fluridone.


743+Sulcotrione, 743+Mesotrione, 743+Topramezone, 743+Tembotrione, 743+Bicyclopyrone, 743+Tefuryltrione, 743+Benzobicyclon, 743+Lancotrione, 743+Shuangzuocaotong, 743+Huanbifucaotong, 743+S anzuohuangc aotong, 743+Benzuofucaotong, 743+Pyrasulfotole, 743+Pyrazolate, 743+Benzofenap, 743+Tolpyralate, 743+Fenquinotrione, 743+Isoxaflutole, 743+Fluroxypyr or esters thereof, 743+Halauxifen-methyl, 743+Florpyrauxifen-benzyl, 743+Quinclorac, 743+Quinmerac, 743+Chipton or salts/esters thereof, 743+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 743+MCPB or salts/esters thereof, 743+2,4-D or salts/esters thereof, 743+Dichlorprop or salts/esters thereof, 743+2,4-DB or salts/esters thereof, 743+Dicamba, 743+Picloram, 743+Trichlopyr, 743+Clopyralid, 743+Triclopyr, 743+Flurochloridone, 743+Flurtamone, 743+Diflufenican, 743+Picolinafen, 743+Beflubutamid, 743+Norflurazon, 743+Fluridone.


744+Sulcotrione, 744+Mesotrione, 744+Topramezone, 744+Tembotrione, 744+Bicyclopyrone, 744+Tefuryltrione, 744+Benzobicyclon, 744+Lancotrione, 744+Shuangzuocaotong, 744+Huanbifucaotong, 744+Sanzuohuangcaotong, 744+Benzuofucaotong, 744+Pyrasulfotole, 744+Pyrazolate, 744+Benzofenap, 744+Tolpyralate, 744+Fenquinotrione, 744+Isoxaflutole, 744+Fluroxypyr or esters thereof, 744+Halauxifen-methyl, 744+Florpyrauxifen-benzyl, 744+Quinclorac, 744+Quinmerac, 744+Chipton or salts/esters thereof, 744+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 744+MCPB or salts/esters thereof, 744+2,4-D or salts/esters thereof, 744+Dichlorprop or salts/esters thereof, 744+2,4-DB or salts/esters thereof, 744+Dicamba, 744+Picloram, 744+Trichlopyr, 744+Clopyralid, 744+Triclopyr, 744+Flurochloridone, 744+Flurtamone, 744+Diflufenican, 744+Picolinafen, 744+Beflubutamid, 744+Norflurazon, 744+Fluridone.


745+Sulcotrione, 745+Mesotrione, 745+Topramezone, 745+Tembotrione, 745+Bicyclopyrone, 745+Tefuryltrione, 745+Benzobicyclon, 745+Lancotrione, 745+Shuangzuocaotong, 745+Huanbifucaotong, 745+Sanzuohuangcaotong, 745+Benzuofucaotong, 745+Pyrasulfotole, 745+Pyrazolate, 745+Benzofenap, 745+Tolpyralate, 745+Fenquinotrione, 745+Isoxaflutole, 745+Fluroxypyr or esters thereof, 745+Halauxifen-methyl, 745+Florpyrauxifen-benzyl, 745+Quinclorac, 745+Quinmerac, 745+Chipton or salts/esters thereof, 745+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 745+MCPB or salts/esters thereof, 745+2,4-D or salts/esters thereof, 745+Dichlorprop or salts/esters thereof, 745+2,4-DB or salts/esters thereof, 745+Dicamba, 745+Picloram, 745+Trichlopyr, 745+Clopyralid, 745+Triclopyr, 745+Flurochloridone, 745+Flurtamone, 745+Diflufenican, 745+Picolinafen, 745+Beflubutamid, 745+Norflurazon, 745+Fluridone.


746+Sulcotrione, 746+Mesotrione, 746+Topramezone, 746+Tembotrione, 746+Bicyclopyrone, 746+Tefuryltrione, 746+Benzobicyclon, 746+Lancotrione, 746+Shuangzuocaotong, 746+Huanbifucaotong, 746+Sanzuohuangcaotong, 746+Benzuofucaotong, 746+Pyrasulfotole, 746+Pyrazolate, 746+Benzofenap, 746+Tolpyralate, 746+Fenquinotrione, 746+Isoxaflutole, 746+Fluroxypyr or esters thereof, 746+Halauxifen-methyl, 746+Florpyrauxifen-benzyl, 746+Quinclorac, 746+Quinmerac, 746+Chipton or salts/esters thereof, 746+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 746+MCPB or salts/esters thereof, 746+2,4-D or salts/esters thereof, 746+Dichlorprop or salts/esters thereof, 746+2,4-DB or salts/esters thereof, 746+Dicamba, 746+Picloram, 746+Trichlopyr, 746+Clopyralid, 746+Triclopyr, 746+Flurochloridone, 746+Flurtamone, 746+Diflufenican, 746+Picolinafen, 746+Beflubutamid, 746+Norflurazon, 746+Fluridone.


779+Sulcotrione, 779+Mesotrione, 779+Topramezone, 779+Tembotrione, 779+Bicyclopyrone, 779+Tefuryltrione, 779+Benzobicyclon, 779+Lancotrione, 779+Shuangzuocaotong, 779+Huanbifucaotong, 779+Sanzuohuangcaotong, 779+Benzuofucaotong, 779+Pyrasulfotole, 779+Pyrazolate, 779+Benzofenap, 779+Tolpyralate, 779+Fenquinotrione, 779+Isoxaflutole, 779+Fluroxypyr or esters thereof, 779+Halauxifen-methyl, 779+Florpyrauxifen-benzyl, 779+Quinclorac, 779+Quinmerac, 779+Chipton or salts/esters thereof, 779+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 779+MCPB or salts/esters thereof, 779+2,4-D or salts/esters thereof, 779+Dichlorprop or salts/esters thereof, 779+2,4-DB or salts/esters thereof, 779+Dicamba, 779+Picloram, 779+Trichlopyr, 779+Clopyralid, 779+Triclopyr, 779+Flurochloridone, 779+Flurtamone, 779+Diflufenican, 779+Picolinafen, 779+Beflubutamid, 779+Norflurazon, 779+Fluridone.


963+Sulcotrione, 963+Mesotrione, 963+Topramezone, 963+Tembotrione, 963+Bicyclopyrone, 963+Tefuryltrione, 963+Benzobicyclon, 963+Lancotrione, 963+Shuangzuocaotong, 963+Huanbifucaotong, 963+Sanzuohuangcaotong, 963+Benzuofucaotong, 963+Pyrasulfotole, 963+Pyrazolate, 963+Benzofenap, 963+Tolpyralate, 963+Fenquinotrione, 963+Isoxaflutole, 963+Fluroxypyr or esters thereof, 963+Halauxifen-methyl, 963+Florpyrauxifen-benzyl, 963+Quinclorac, 963+Quinmerac, 963+Chipton or salts/esters thereof, 963+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 963+MCPB or salts/esters thereof, 963+2,4-D or salts/esters thereof, 963+Dichlorprop or salts/esters thereof, 963+2,4-DB or salts/esters thereof, 963+Dicamba, 963+Picloram, 963+Trichlopyr, 963+Clopyralid, 963+Triclopyr, 963+Flurochloridone, 963+Flurtamone, 963+Diflufenican, 963+Picolinafen, 963+Beflubutamid, 963+Norflurazon, 963+Fluridone.


1000+Sulcotrione, 1000+Mesotrione, 1000+Topramezone, 1000+Tembotrione, 1000+Bicyclopyrone, 1000+Tefuryltrione, 1000+Benzobicyclon, 1000+Lancotrione, 1000+Shuangzuocaotong, 1000+Huanbifucaotong, 1000+Sanzuohuangcaotong, 1000+Benzuofucaotong, 1000+Pyrasulfotole, 1000+Pyrazolate, 1000+Benzofenap, 1000+Tolpyralate, 1000+Fenquinotrione, 1000+Isoxaflutole, 1000+Fluroxypyr or esters thereof, 1000+Halauxifen-methyl, 1000+Florpyrauxifen-benzyl, 1000+Quinclorac, 1000+Quinmerac, 1000+Chipton or salts/esters thereof, 1000+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 1000+MCPB or salts/esters thereof, 1000+2,4-D or salts/esters thereof, 1000+Dichlorprop or salts/esters thereof, 1000+2,4-DB or salts/esters thereof, 1000+Dicamba, 1000+Picloram, 1000+Trichlopyr, 1000+Clopyralid, 1000+Triclopyr, 1000+Flurochloridone, 1000+Flurtamone, 1000+Diflufenican, 1000+Picolinafen, 1000+Beflubutamid, 1000+Norflurazon, 1000+Fluridone.


1-3+Sulcotrione, 1-3+Mesotrione, 1-3+Topramezone, 1-3+Tembotrione, 1-3+Bicyclopyrone, 1-3+Tefuryltrione, 1-3+Benzobicyclon, 1-3+Lancotrione, 1-3+Shuangzuocaotong, 1-3+Huanbifucaotong, 1-3+Sanzuohuangcaotong, 1-3+Benzuofucaotong, 1-3+Pyrasulfotole, 1-3+Pyrazolate, 1-3+Benzofenap, 1-3+Tolpyralate, 1-3+Fenquinotrione, 1-3+Isoxaflutole, 1-3+Fluroxypyr or esters thereof, 1-3+Halauxifen-methyl, 1-3+Florpyrauxifen-benzyl, 1-3+Quinclorac, 1-3+Quinmerac, 1-3+Chipton or salts/esters thereof, 1-3+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 1-3+MCPB or salts/esters thereof, 1-3+2,4-D or salts/esters thereof, 1-3+Dichlorprop or salts/esters thereof, 1-3+2,4-DB or salts/esters thereof, 1-3+Dicamba, 1-3+Picloram, 1-3+Trichlopyr, 1-3+Clopyralid, 1-3+Triclopyr, 1-3+Flurochloridone, 1-3+Flurtamone, 1-3+Diflufenican, 1-3+Picolinafen, 1-3+Beflubutamid, 1-3+Norflurazon, 1-3+Fluridone. 1-39+Sulcotrione, 1-39+Mesotrione, 1-39+Topramezone, 1-39+Tembotrione, 1-39+Bicyclopyrone, 1-39+Tefuryltrione, 1-39+Benzobicyclon, 1-39+Lancotrione, 1-39+Shuangzuocaotong, 1-39+Huanbifucaotong, 1-39+Sanzuohuangcaotong, 1-39+Benzuofucaotong, 1-39+Pyrasulfotole, 1-39+Pyrazolate, 1-39+Benzofenap, 1-39+Tolpyralate, 1-39+Fenquinotrione, 1-39+Isoxaflutole, 1-39+Fluroxypyr or esters thereof, 1-39+Halauxifen-methyl, 1-39+Florpyrauxifen-benzyl, 1-39+Quinclorac, 1-39+Quinmerac, 1-39+Chipton or salts/esters thereof, 1-39+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 1-39+MCPB or salts/esters thereof, 1-39+2,4-D or salts/esters thereof, 1-39+Dichlorprop or salts/esters thereof, 1-39+2,4-DB or salts/esters thereof, 1-39+Dicamba, 1-39+Picloram, 1-39+Trichlopyr, 1-39+Clopyralid, 1-39+Triclopyr, 1-39+Flurochloridone, 1-39+Flurtamone, 1-39+Diflufenican, 1-39+Picolinafen, 1-39+Beflubutamid, 1-39+Norflurazon, 1-39+Fluridone. 1-43+Sulcotrione, 1-43+Mesotrione, 1-43+Topramezone, 1-43+Tembotrione, 1-43+Bicyclopyrone, 1-43+Tefuryltrione, 1-43+Benzobicyclon, 1-43+Lancotrione, 1-43+Shuangzuocaotong, 1-43+Huanbifucaotong, 1-43+Sanzuohuangcaotong, 1-43+Benzuofucaotong, 1-43+Pyrasulfotole, 1-43+Pyrazolate, 1-43+Benzofenap, 1-43+Tolpyralate, 1-43+Fenquinotrione, 1-43+Isoxaflutole, 1-43+Fluroxypyr or esters thereof, 1-43+Halauxifen-methyl, 1-43+Florpyrauxifen-benzyl, 1-43+Quinclorac, 1-43+Quinmerac, 1-43+Chipton or salts/esters thereof, 1-43+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 1-43+MCPB or salts/esters thereof, 1-43+2,4-D or salts/esters thereof, 1-43+Dichlorprop or salts/esters thereof, 1-43+2,4-DB or salts/esters thereof, 1-43+Dicamba, 1-43+Picloram, 1-43+Trichlopyr, 1-43+Clopyralid, 1-43+Triclopyr, 1-43+Flurochloridone, 1-43+Flurtamone, 1-43+Diflufenican, 1-43+Picolinafen, 1-43+Beflubutamid, 1-43+Norflurazon, 1-43+Fluridone.


1-55+Sulcotrione, 1-55+Mesotrione, 1-55+Topramezone, 1-55+Tembotrione, 1-55+Bicyclopyrone, 1-55+Tefuryltrione, 1-55+Benzobicyclon, 1-55+Lancotrione, 1-55+Shuangzuocaotong, 1-55+Huanbifucaotong, 1-55+Sanzuohuangcaotong, 1-55+Benzuofucaotong, 1-55+Pyrasulfotole, 1-55+Pyrazolate, 1-55+Benzofenap, 1-55+Tolpyralate, 1-55+Fenquinotrione, 1-55+Isoxaflutole, 1-55+Fluroxypyr or esters thereof, 1-55+Halauxifen-methyl, 1-55+Florpyrauxifen-benzyl, 1-55+Quinclorac, 1-55+Quinmerac, 1-55+Chipton or salts/esters thereof, 1-55+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 1-55+MCPB or salts/esters thereof, 1-55+2,4-D or salts/esters thereof, 1-55+Dichlorprop or salts/esters thereof, 1-55+2,4-DB or salts/esters thereof, 1-55+Dicamba, 1-55+Picloram, 1-55+Trichlopyr, 1-55+Clopyralid, 1-55+Triclopyr, 1-55+Flurochloridone, 1-55+Flurtamone, 1-55+Diflufenican, 1-55+Picolinafen, 1-55+Beflubutamid, 1-55+Norflurazon, 1-55+Fluridone.


1-82+Sulcotrione, 1-82+Mesotrione, 1-82+Topramezone, 1-82+Tembotrione, 1-82+Bicyclopyrone, 1-82+Tefuryltrione, 1-82+Benzobicyclon, 1-82+Lancotrione, 1-82+Shuangzuocaotong, 1-82+Huanbifucaotong, 1-82+Sanzuohuangcaotong, 1-82+Benzuofucaotong, 1-82+Pyrasulfotole, 1-82+Pyrazolate, 1-82+Benzofenap, 1-82+Tolpyralate, 1-82+Fenquinotrione, 1-82+Isoxaflutole, 1-82+Fluroxypyr or esters thereof, 1-82+Halauxifen-methyl, 1-82+Florpyrauxifen-benzyl, 1-82+Quinclorac, 1-82+Quinmerac, 1-82+Chipton or salts/esters thereof, 1-82+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 1-82+MCPB or salts/esters thereof, 1-82+2,4-D or salts/esters thereof, 1-82+Dichlorprop or salts/esters thereof, 1-82+2,4-DB or salts/esters thereof, 1-82+Dicamba, 1-82+Picloram, 1-82+Trichlopyr, 1-82+Clopyralid, 1-82+Triclopyr, 1-82+Flurochloridone, 1-82+Flurtamone, 1-82+Diflufenican, 1-82+Picolinafen, 1-82+Beflubutamid, 1-82+Norflurazon, 1-82+Fluridone.


1-86+Sulcotrione, 1-86+Mesotrione, 1-86+Topramezone, 1-86+Tembotrione, 1-86+Bicyclopyrone, 1-86+Tefuryltrione, 1-86+Benzobicyclon, 1-86+Lancotrione, 1-86+Shuangzuocaotong, 1-86+Huanbifucaotong, 1-86+Sanzuohuangcaotong, 1-86+Benzuofucaotong, 1-86+Pyrasulfotole, 1-86+Pyrazolate, 1-86+Benzofenap, 1-86+Tolpyralate, 1-86+Fenquinotrione, 1-86+Isoxaflutole, 1-86+Fluroxypyr or esters thereof, 1-86+Halauxifen-methyl, 1-86+Florpyrauxifen-benzyl, 1-86+Quinclorac, 1-86+Quinmerac, 1-86+Chipton or salts/esters thereof, 1-86+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 1-86+MCPB or salts/esters thereof, 1-86+2,4-D or salts/esters thereof, 1-86+Dichlorprop or salts/esters thereof, 1-86+2,4-DB or salts/esters thereof, 1-86+Dicamba, 1-86+Picloram, 1-86+Trichlopyr, 1-86+Clopyralid, 1-86+Triclopyr, 1-86+Flurochloridone, 1-86+Flurtamone, 1-86+Diflufenican, 1-86+Picolinafen, 1-86+Beflubutamid, 1-86+Norflurazon, 1-86+Fluridone.


1-226+Sulcotrione, 1-226+Mesotrione, 1-226+Topramezone, 1-226+Tembotrione, 1-226+Bicyclopyrone, 1-226+Tefuryltrione, 1-226+Benzobicyclon, 1-226+Lancotrione, 1-226+Shuangzuocaotong, 1-226+Huanbifucaotong, 1-226+Sanzuohuangcaotong, 1-226+Benzuofucaotong, 1-226+Pyrasulfotole, 1-226+Pyrazolate, 1-226+Benzofenap, 1-226+Tolpyralate, 1-226+Fenquinotrione, 1-226+Isoxaflutole, 1-226+Fluroxypyr or esters thereof, 1-226+Halauxifen-methyl, 1-226+Florpyrauxifen-benzyl, 1-226+Quinclorac, 1-226+Quinmerac, 1-226+Chipton or salts/esters thereof, 1-226+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 1-226+MCPB or salts/esters thereof, 1-226+2,4-D or salts/esters thereof, 1-226+Dichlorprop or salts/esters thereof, 1-226+2,4-DB or salts/esters thereof, 1-226+Dicamba, 1-226+Picloram, 1-226+Trichlopyr, 1-226+Clopyralid, 1-226+Triclopyr, 1-226+Flurochloridone, 1-226+Flurtamone, 1-226+Diflufenican, 1-226+Picolinafen, 1-226+Beflubutamid, 1-226+Norflurazon, 1-226+Fluridone.


1-227+Sulcotrione, 1-227+Mesotrione, 1-227+Topramezone, 1-227+Tembotrione, 1-227+Bicyclopyrone, 1-227+Tefuryltrione, 1-227+Benzobicyclon, 1-227+Lancotrione, 1-227+Shuangzuocaotong, 1-227+Huanbifucaotong, 1-227+Sanzuohuangcaotong, 1-227+Benzuofucaotong, 1-227+Pyrasulfotole, 1-227+Pyrazolate, 1-227+Benzofenap, 1-227+Tolpyralate, 1-227+Fenquinotrione, 1-227+Isoxaflutole, 1-227+Fluroxypyr or esters thereof, 1-227+Halauxifen-methyl, 1-227+Florpyrauxifen-benzyl, 1-227+Quinclorac, 1-227+Quinmerac, 1-227+Chipton or salts/esters thereof, 1-227+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 1-227+MCPB or salts/esters thereof, 1-227+2,4-D or salts/esters thereof, 1-227+Dichlorprop or salts/esters thereof, 1-227+2,4-DB or salts/esters thereof, 1-227+Dicamba, 1-227+Picloram, 1-227+Trichlopyr, 1-227+Clopyralid, 1-227+Triclopyr, 1-227+Flurochloridone, 1-227+Flurtamone, 1-227+Diflufenican, 1-227+Picolinafen, 1-227+Beflubutamid, 1-227+Norflurazon, 1-227+Fluridone.


1-228+Sulcotrione, 1-228+Mesotrione, 1-228+Topramezone, 1-228+Tembotrione, 1-228+Bicyclopyrone, 1-228+Tefuryltrione, 1-228+Benzobicyclon, 1-228+Lancotrione, 1-228+Shuangzuocaotong, 1-228+Huanbifucaotong, 1-228+Sanzuohuangcaotong, 1-228+Benzuofucaotong, 1-228+Pyrasulfotole, 1-228+Pyrazolate, 1-228+Benzofenap, 1-228+Tolpyralate, 1-228+Fenquinotrione, 1-228+Isoxaflutole, 1-228+Fluroxypyr or esters thereof, 1-228+Halauxifen-methyl, 1-228+Florpyrauxifen-benzyl, 1-228+Quinclorac, 1-228+Quinmerac, 1-228+Chipton or salts/esters thereof, 1-228+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 1-228+MCPB or salts/esters thereof, 1-228+2,4-D or salts/esters thereof, 1-228+Dichlorprop or salts/esters thereof, 1-228+2,4-DB or salts/esters thereof, 1-228+Dicamba, 1-228+Picloram, 1-228+Trichlopyr, 1-228+Clopyralid, 1-228+Triclopyr, 1-228+Flurochloridone, 1-228+Flurtamone, 1-228+Diflufenican, 1-228+Picolinafen, 1-228+Beflubutamid, 1-228+Norflurazon, 1-228+Fluridone.


1-229+Sulcotrione, 1-229+Mesotrione, 1-229+Topramezone, 1-229+Tembotrione, 1-229+Bicyclopyrone, 1-229+Tefuryltrione, 1-229+Benzobicyclon, 1-229+Lancotrione, 1-229+Shuangzuocaotong, 1-229+Huanbifucaotong, 1-229+Sanzuohuangcaotong, 1-229+Benzuofucaotong, 1-229+Pyrasulfotole, 1-229+Pyrazolate, 1-229+Benzofenap, 1-229+Tolpyralate, 1-229+Fenquinotrione, 1-229+Isoxaflutole, 1-229+Fluroxypyr or esters thereof, 1-229+Halauxifen-methyl, 1-229+Florpyrauxifen-benzyl, 1-229+Quinclorac, 1-229+Quinmerac, 1-229+Chipton or salts/esters thereof, 1-229+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 1-229+MCPB or salts/esters thereof, 1-229+2,4-D or salts/esters thereof, 1-229+Dichlorprop or salts/esters thereof, 1-229+2,4-DB or salts/esters thereof, 1-229+Dicamba, 1-229+Picloram, 1-229+Trichlopyr, 1-229+Clopyralid, 1-229+Triclopyr, 1-229+Flurochloridone, 1-229+Flurtamone, 1-229+Diflufenican, 1-229+Picolinafen, 1-229+Beflubutamid, 1-229+Norflurazon, 1-229+Fluridone.


1-230+Sulcotrione, 1-230+Mesotrione, 1-230+Topramezone, 1-230+Tembotrione, 1-230+Bicyclopyrone, 1-230+Tefuryltrione, 1-230+Benzobicyclon, 1-230+Lancotrione, 1-230+Shuangzuocaotong, 1-230+Huanbifucaotong, 1-230+Sanzuohuangcaotong, 1-230+Benzuofucaotong, 1-230+Pyrasulfotole, 1-230+Pyrazolate, 1-230+Benzofenap, 1-230+Tolpyralate, 1-230+Fenquinotrione, 1-230+Isoxaflutole, 1-230+Fluroxypyr or esters thereof, 1-230+Halauxifen-methyl, 1-230+Florpyrauxifen-benzyl, 1-230+Quinclorac, 1-230+Quinmerac, 1-230+Chipton or salts/esters thereof, 1-230+2-methyl 4-chlorophenoxypropionic acid or salts/esters thereof, 1-230+MCPB or salts/esters thereof, 1-230+2,4-D or salts/esters thereof, 1-230+Dichlorprop or salts/esters thereof, 1-230+2,4-DB or salts/esters thereof, 1-230+Dicamba, 1-230+Picloram, 1-230+Trichlopyr, 1-230+Clopyralid, 1-230+Triclopyr, 1-230+Flurochloridone, 1-230+Flurtamone, 1-230+Diflufenican, 1-230+Picolinafen, 1-230+Beflubutamid, 1-230+Norflurazon, 1-230+Fluridone.


Wherein, the actual control effect of the combination of the above components (i) and (ii) on weeds were tested with postemergence applicaitons, that is, when the weeds were in the 3-4 leaf stage, the combination mentioned above diluted with 30 kg/667 m2 water were sprayed uniformly to the stems and leaves of the weed by the hand sprayer. 20 days after treatment, Theoretical fresh weight inhibition rate of a combination of two active ingredients in each group was calculated by the Cowing method (E0=X+Y−X*Y/100), and then compared with an actually measured inhibition rate (E), thereby effect of the combination (hereafter referred to as combined effect) on weeds was evaluated: the value of E−E0, which was greater than 10%, corresponded to a synergistic effect, the value of E−E0, which was less than −10%, corresponded to an antagonistic effect, and the value of E−E0, which was from −10% to 10%, corresponded to an additional effect. An optimum ratio of the two active ingredients was determined by the actual control effect, characteristics of herbicides, and balance of a corresponding formula. Wherein, in the formula, X represented the fresh weight inhibition rate of the active ingredient A in a dosage of P, and Y represented the fresh weight inhibition rate of the active ingredient B in a dosage of Q. The statistic results are shown in Table 6.









TABLE 6







Actual control effect and synergistic effect of the mixture of (i) and (ii) in weeds (Gowing method)



















Inhibitory
Inhibitory









effect of
effect of






component (i)
component (ii)






when applied
when applied


Component (i)/

(i) + (ii)
Weed
alone at
alone at
E
E0
E − E0


Compound No.
Component (ii)
g a.i./ha
species
same dose
same dose (%)
(%)
(%)
(%)


















1
Sulcotrione
30 + 50

Abutilon

20
30
100
44
56






theophrasti



1
Mesotrione
30 + 30

Abutilon

20
40
100
52
48






theophrasti



1
Topramezone
30 + 5 

Abutilon

20
40
100
52
48






theophrasti



1
Tembotrione
30 + 15

Abutilon

20
30
100
44
56






theophrasti



1
Bicyclopyrone
30 + 15

Abutilon

20
40
100
52
48






theophrasti



1
Tefuryltrione
30 + 50

Abutilon

20
40
80
52
28






theophrasti



1
Benzobicyclon
 30 + 150

Abutilon

20
50
100
60
40






theophrasti



1
Lancotrione
30 + 50

Abutilon

20
40
100
52
48






theophrasti



1
Shuangzuocaotong
30 + 5 

Sisymbrium

20
40
100
52
48






sophia



1
Huanbifucaotong
30 + 30

Abutilon

20
30
100
44
56






theophrasti



1
Sanzuohuangcaotong
30 + 30

Abutilon

20
30
100
44
56






theophrasti



1
Benzuofucaotong
30 + 15

Abutilon

20
40
100
52
48






theophrasti



1
Pyrasulfotole
30 + 15

Abutilon

20
50
100
60
40






theophrasti



1
Benzofenap
 30 + 150

Abutilon

20
40
100
52
48






theophrasti



1
Tolpyralate
30 + 5 

Abutilon

20
50
100
60
40






theophrasti



1
Isoxaflutole
30 + 30

Abutilon

20
30
100
44
56






theophrasti



1
Fluroxypyr
30 + 30

Galium

20
40
80
52
28






aparine



1
Halauxifen-
30 + 2 

Abutilon

20
40
100
52
48



methyl


theophrasti



1
Florpyrauxifen-
30 + 2 

Abutilon

20
45
100
56
44



benzyl


theophrasti



1
Quinclorac
30 + 50

Galium

20
50
80
60
20






aparine



1
Chipton
30 + 60

Sisymbrium

20
40
80
52
28



sodium salt


sophia



1
2-methyl 4-
 30 + 100

Sisymbrium

20
30
75
44
31



chlorophenoxy


sophia




propionic acid


1
MCPB
 30 + 200

Sisymbrium

20
40
85
52
33






sophia



1
2,4-D iso-octyl
30 + 50

Sisymbrium

20
40
85
52
33



ester


sophia



1
Dichlorprop
 30 + 100

Sisymbrium

20
40
100
52
48






sophia



1
2,4-DB
 30 + 200

Sisymbrium

20
50
90
60
30






sophia



1
Dicamba
30 + 10

Sisymbrium

20
30
75
44
31






sophia



1
Picloram
30 + 50

Abutilon

20
40
80
52
28






theophrasti



1
Trichlopyr
30 + 50

Abutilon

20
40
70
52
18






theophrasti



1
Clopyralid
30 + 50

Galinsoga

30
40
85
58
27






parviflora



1
Triclopyr
30 + 50

Abutilon

20
35
75
48
27






theophrasti



1
Flurochloridone
 30 + 100

Galium

20
40
90
52
38






aparine



1
Flurtamone
 30 + 100

Galium

20
35
85
48
37






aparine



1
Diflufenican
 30 + 100

Veronica

30
45
90
61.5
28.5






polita



1
Picolinafen
30 + 50

Abutilon

20
30
85
44
41






theophrasti



1
Beflubutamid
 30 + 200

Abutilon

20
40
100
52
48






theophrasti



1
Norflurazon
 30 + 300

Abutilon

20
50
85
60
25






theophrasti



1
Fluridone
 30 + 100

Abutilon

20
45
85
56
29






theophrasti










At the same time, it is found after several tests that similar herbicidal effects were achieved when other components (i) of the present invention were combined with the component (ii). In addition, the compound and the composition of the present invention have good selectivity to many gramineae grasses such as zoysia japonica, Bermuda grass, tall fescue, bluegrass, ryegrass and seashore paspalum etc, and are able to control many important grass weeds and broadleaf weeds. The compounds also show excellent selectivity and commercial value in the tests on wheat, corn, rice, sugarcane, soybean, cotton, oil sunflower, potato, orchards and vegetables in different herbicide application methods.

Claims
  • 1. A pyridazinol compound of Formula I or a derivative thereof:
  • 2. The pyridazinol compound or a derivative thereof according to claim 1, wherein, X is halogenated C1˜C8 alkyl, cyano, C1˜C8 alkyl, C1˜C8 alkoxy, halogenated C1˜C8 alkoxy, R1R2N—(C═O)—, R1R2N—, hydroxy, or aryl, said aryl is unsubstituted or substituted with 1˜5 substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C8 alkyl, C3˜C8 cycloalkyl, C3˜C8 cycloalkyl-C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C1˜C8 alkoxy, C1˜C8 alkylcarbonyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylsulfonyl, C1˜C8 alkylamino, and C1˜C8 alkylcarbonyloxy;A is selected from the group consisting of C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C3˜C8 cycloalkyl, C3˜C8 cycloalkenyl, C3˜C8 cycloalkyl-C1˜C8 alkyl, 5- to 14-membered aryl, 5- to 14-membered heteroaryl, and 5- to 14-membered aliphatic heterocyclyl, each of which is unsubstituted or substituted; wherein,when being substituted, said C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C3˜CS cycloalkyl, C3˜C6 cycloalkenyl, or C3˜C8 cycloalkyl-C1˜C8 alkyl is substituted with one or more substituents independently selected from the group consisting of halogen, cyano, nitro, azido, aryl, heteroaryl, said aryl or heteroaryl is unsubstituted or independently substituted with 15 groups selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C8 alkyl, C3˜C8 cycloalkyl, C3˜C8 cycloalkenyl, C3˜C8 cycloalkyl-C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C1˜C8 alkoxy, C1˜C8 alkylcarbonyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylsulfonyl, C1˜C8 alkylamino, and C1˜C8 alkylcarbonyloxy, —(CH2)n—O—(CH2)p—, —(CH2)n—S—(CH2)p—, —(CH2)n—NR3—(CH2)p—, R—O—, R—O—(CH2)p—O—, R—O—(CH2)p—S—, R—S—, R—S—(CH2)p—O—, R—S—(CH2)p—S—, R—O—(C═O)—(CH2)q—(O)m—, R—O—(CH2)n—(C═O)—(O)m—, R—O—(CH2)n—(C═O)—, R—S—(C═S)—(CH2)q—(S)m—, R—S—(CH2)n—(C═S)—(S)m—, R—S—(CH2)n—(C═S)—, R—O—(C═O)—(CH2)q—(S)m—, R—O—(CH2)n—(C═O)—(S)m—, R—O—(C═S)—(CH2)q—(O)m—, R—O—(CH2)n—(C═S)—(O)m—, R—O—(CH2)n—(C═S)—, R—S—(C═O)—(CH2)q—(O)m—, R—S—(CH2)n—(C═O)—(O)m—, R—S—(CH2)n—(C═O)—, R—O—(C═S)—(CH2)q—(S)m—, R—O—(CH2)n—(C═S)—(S)m—, R—S—(C═O)—(CH2)q—(S)m—, R—S—(CH2)n—(C═O)—(S)m—, R—S—(C═S)—(CH2)q—(O)m—, R—S—(CH2)n—(C═S)—(O)m—, R—(C═O)—, R—(C═S)—, R—(C═O)—O—, R—(C═S)—S—, R—(C═O)—S—, R—(C═S)—O—, R—SO—(O)m—, R—SO—(S)m—, R—SO—(NR3)m—, R—SO2—(O)m—, R—SO2—(S)m—, R—SO2(NR3)m, R1R2N—, R1R2N—O—(CH2)q—(O)m—, R1R2N—(CH2)n—O—, R1R2N—O—(CH2)q—(S)m—, R1R2N—O—(CH2)q—(NR3)m—, R1R2N—(C═O)—(CH2)q—(O)m—, R1R2N—(CH2)n—(C═O)—(O)m—, R1R2N—(CH2)n—(C═O)—, R1R2N—(C═O)—(CH2)q—(S)m—, R1R2N—(CH2)n—(C═O)—(S)m—, R1R2N—(C═O)—(CH2)q—(NR3)m—, R1R2N—(CH2)n—(C═O)—(NR3)m—, R1R2N—SO2—(CH2)q—(O)m—, R1R2N—(CH2)n—SO2—(O)m—, R1R2N—(CH2)n—SO2—, R1R2N—SO2—(CH2)q—(S)m—, R1R2N—(CH2)n—SO2—(S)m—, R1R2N—SO2—(CH2)q—(NR3)m—, R1R2N—(CH2)n—SO2—(NR3)m—, R1R2P(O)—, R1R2R3SiO—, R1R2R3Si—(CH═CH)m—, R1R2C═N—(O)m—, and R1R2C═N—NH—;when being substituted, each of said 5- to 14-membered aryl, 5- to 14-membered heteroaryl or 5- to 14-membered aliphatic heterocyclyl is independently substituted with one or more substituents selected from the group consisting of halogen, cyano, nitro, azido, a halogen-containing or not containing group selected from C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C3˜C8 cycloalkyl, C3˜C8 cycloalkenyl, and C3˜CS cycloalkyl-C1˜C8 alkyl, aryl, aryl-C1˜C8 alkyl, heteroaryl, heteroaryl-C1˜C8 alkyl, aliphatic heterocyclyl, aliphatic heterocyclyl-C1˜C8 alkyl, each of said aryl, aryl-C1˜CS alkyl, heteroaryl, heteroaryl-C1˜C8 alkyl, aliphatic heterocyclyl, or aliphatic heterocyclyl-C1˜C8 alkyl is unsubstituted or substituted with 15 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C8 alkyl, C3˜C8 cycloalkyl, C3˜C8 cycloalkenyl, C3˜C8 cycloalkyl-C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C1˜C8 alkoxy, C1˜C8 alkylcarbonyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylsulfonyl, C1˜C8 alkylamino, and C1˜C8 alkylcarbonyloxy, R—O—(CH2)n—, R—O—(CH2)p—O—(CH2)q—, R—O—(CH2)p—S—(CH2)q—, R—S—(CH2)n—, R—S—(CH2)p—O—(CH2)q—, R—S—(CH2)p—S—(CH2)q—, R—O—(CH2)n—(C═O)—(CH2)q—(O)m—, R—S—(CH2)n—(C═S)—(CH2)q—, R—O—(CH2)n—(C═S)—(CH2)q—, R—S—(CH2)n—(C═O)—(CH2)q—, R—S—(C═S)—(CH2)q—(S)m—, R—O—(CH2)n—(C═O)—(CH2)q—(S)m—, R—O—(C═S)—(CH2)q—(O)m—, R—S—(C═O)—(CH2)q—(O)m—, R—O—(C═S)—(CH2)q—(S)m—, R—S—(C═O)—(CH2)q—(S)m—, R—S—(C═S)—(CH2)q—(O)m—, R—S—(CH2)n—(C═S)—(S)m—, R—O—(CH2)n—(C═S)—(O)m—, R—S—(CH2)n—(C═O)—(O)m—, R—O—(CH2)n—(C═S)—(S)m—, R—S—(CH2)n—(C═O)—(S)m—, R—S—(CH2)n—(C═S)—(O)m—, R—(C═O)—(CH2)n—, R—(C═S)—, R—(C═O)—(CH2)n—O—(CH2)q—, R—(C═S)—(CH2)n—S—, R—(C═O)—(CH2)n—S—, R—(C═S)—(CH2)n—O—, R—(C═S)—S—(CH2)q—, R—(C═O)—S—(CH2)q—, R—(C═S)—O—(CH2)q—, R—SO—(O)m—, R—SO—(S)m—, R—SO(NR3)m, R—SO2—(CH2)n—(O)m, R—SO2—(S)m—, R—SO2(CH2)n—(NR3)m—, R—SO—(CH2)n—, R1R2N—(CH2)n—, R1R2N—(CH2)n—O—(CH2)q—, R1R2N—(C═O)—(CH2)q—(O)m—, R1R2N—(CH2)n—(C═O)—(CH2)q—, R1R2N—(CH2)n—(C═O)—(O)m—, R1R2N—(CH2)n—(C═O)—(S)m—, R1R2N—(CH2)n—(C═O)—(NR3)m—, R1R2N—(CH2)n—SO2—(CH2)q—(O)m—, R1R2N—(CH2)n—SO2—(S)m—, R1R2N—(CH2)n—SO2—(NR3)m—, R1R2N—(C═O)—(CH2)n—(O)m—, R1R2N—(C═O)—(CH2)n—(S)m—, R1R2N—(C═O)—(CH2)n—(NR3)m—, R1R2N—SO2—(CH2)q—(S)m—, R1R2N—SO2—(CH2)q—(NR3)m—, R1R2N—(CH2)n—O—, R1R2N—O—(CH2)q—, R1R2P(O)—(O)m—, R1R2R3SiO—, R1R2R3Si—(CH═CH)m, R1R2C═N—(O)m—, and R1R2C═N—NH—;m is 0 or 1, n and q are independently an integer from 0 to 6, p is an integer from 1 to 6;R is hydrogen, a halogen-containing or not containing group selected from C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C3˜C8 cycloalkyl, C3˜C8 cycloalkenyl, and C3˜C8 cycloalkyl-C1˜C8 alkyl, aryl, aryl-C1˜C8 alkyl, heteroaryl, or heteroaryl-C1˜C8 alkyl, each of said aryl, aryl-C1˜C8 alkyl, heteroaryl, or heteroaryl-C1˜C8 alkyl is unsubstituted or substituted with 1˜5 groups substituents independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C8 alkyl, C3˜C8 cycloalkyl, C3˜C8 cycloalkenyl, C3˜C8 cycloalkyl-C1˜C8 alkyl, C2˜C6 alkenyl, C2˜C8 alkynyl, C1˜C8 alkoxy, C1˜C8 alkylcarbonyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylsulfonyl, C1˜C8 alkylamino, and C1˜C8 alkylcarbonyloxy;R1, R2, R3 are each independently hydrogen, nitro, hydroxy, amino, a halogen-containing or not containing group selected from C1˜CS alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C3˜C8 cycloalkyl, C3˜C8 cycloalkenyl, C3˜C8 cycloalkyl-C1˜C8 alkyl, C1˜C8 alkoxy, C2˜C8 alkenyloxy, C2˜C8 alkynyloxy, C3˜C8 cycloalkyloxy, C1˜C8 alkoxy-C1˜C8 alkyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylcarbonyl-C1˜C8 alkyl, C1˜C8 alkylsulfanylcarbonyl, C1˜C8 alkylsulfonyl, C1˜C8 alkylsulfonyl-C1˜C8 alkyl, C1˜C8 alkylcarbonyl, C1˜C8 alkylcarbonyloxy, C1˜C8 alkylamino, C1˜C8 alkylaminocarbonyl, C1˜C8 alkoxyaminocarbonyl, C1˜C8 alkoxycarbonyl-C1˜C8 alkyl, C1˜C8 alkylaminocarbonyl-C1˜C8 alkyl, triC1˜CS alkylsilyl, and diC1˜C8 alkylphosphonyl, aryl, aryl-C1˜CS alkyl, aryloxy, aryl-C1˜C8 alkyloxy, aryloxy-C1˜C8 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1˜C8 alkyl, heteroaryloxy, heteroaryl-C1˜C8 alkyloxy, heteroaryloxy-C1˜C8 alkyl, heteroarylcarbonyl, heteroarylsulfonyl, aliphatic heterocyclyl, aliphatic heterocyclyl-C1˜C8 alkyl, aliphatic heterocyclyloxy, aliphatic heterocyclyl-C1˜C8 alkyloxy, aliphatic heterocyclyloxy-C1˜C8 alkyl, aliphatic heterocyclylcarbonyl, or aliphatic heterocyclylsulfonyl, each of said aryl, aryl-C1˜C8 alkyl, aryloxy, aryl-C1˜C8 alkyloxy, aryloxy-C1˜C8 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1˜C8 alkyl, heteroaryloxy, heteroaryl-C1˜C8 alkyloxy, heteroaryloxy-C1˜C8 alkyl, heteroarylcarbonyl, heteroarylsulfonyl, aliphatic heterocyclyl, aliphatic heterocyclyl-C1˜C8 alkyl, aliphatic heterocyclyloxy, aliphatic heterocyclyl-C1˜C8 alkyloxy, aliphatic heterocyclyloxy-C1˜C8 alkyl, aliphatic heterocyclylcarbonyl, or aliphatic heterocyclylsulfonyl is unsubstituted or substituted with 1˜5 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C8 alkyl, C3˜C8 cycloalkyl, C3˜C8 cycloalkenyl, C3˜C8 cycloalkyl-C1˜C8 alkyl, C2˜C8 alkenyl, C2˜C8 alkynyl, C1˜C8 alkoxy, C1˜C8 alkylcarbonyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylsulfonyl, C1˜CS alkylamino, and C1˜C8 alkylcarbonyloxy; or R1R2N— forms a 5- to 6-membered heterocyclyl;wherein the derivative is an agriculturally acceptable salt or a compound derivatized from the 4-hydroxy of the pyridazlne ring of the Formula I.
  • 3. The pyridazinol compound or a derivative thereof according to claim 1, wherein, X is halogenated C1˜C6 alkyl;A is selected from the group consisting of C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, 5- to 14-membered aryl, 5- to 14-membered heteroaryl, and 5- to 14-membered aliphatic heterocyclyl, each of which is unsubstituted or substituted; wherein,when being substituted, each of said C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜CS cycloalkyl, C3˜C6 cycloalkenyl, or C3˜C6 cycloalkyl-C1˜C6 alkyl is substituted with one or more substituents independently selected from the group consisting of halogen, cyano, nitro, azido, aryl, heteroaryl, said aryl or heteroaryl is unsubstituted or substituted with 1˜3 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C6 alkyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C1˜C6 alkoxy, C1˜CS alkylcarbonyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylamino, and C1˜C6 alkylcarbonyloxy, —(CH2)n—O—, —(CH2)n—S—, —(CH2)n—NR3—, R—O—, R—O—(CH2)p—O—, R—O—(CH2)p—S—, R—S—, R—S—(CH2)p—O—, R—S—(CH2)p—S—, R—O—(CH2)n—(C═O)—, R—S—(C═S)—, R—O—(C═S)—, R—S—(C═O)—, R—(C═O)—, R—(C═S)—, R—(C═O)—O—, R—(C═S)—S—, R—(C═O)—S—, R—(C═S)—O—, R—SO—, R—SO2—, R1R2N—, R1R2N—O—, R1R2N—(C═O), R1R2N—SO2—, R1R2P(O)—, R1R2R3SiO—, R1R2R3Si—(CH═CH)—, R1R2R3Si—, R1R2C═N—(O)—, R1R2C═N—, and R1R2C═N—NH—;when being substituted, each of said 5- to 14-membered aryl, 5- to 14-membered heteroaryl or 5- to 14-membered aliphatic heterocyclyl is substituted with one or more substituents independently selected from the group consisting of halogen, cyano, nitro, azido, a halogen-containing or not containing group selected from C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, and C3˜C6 cycloalkyl-C1˜C6 alkyl, aryl, aryl-C1˜C6 alkyl, heteroaryl, heteroaryl-C1˜C6 alkyl, aliphatic heterocyclyl, aliphatic heterocyclyl-C1˜C6 alkyl, each of said aryl, aryl-C1˜C6 alkyl, heteroaryl, heteroaryl-C1˜C6 alkyl, aliphatic heterocyclyl, or aliphatic heterocyclyl-C1˜C6 alkyl is unsubstituted or substituted with 1˜5 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C6 alkyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C8 alkynyl, C1˜C8 alkoxy, C1˜C6 alkylcarbonyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylamino, and C1˜C6 alkylcarbonyloxy, R—O—(CH2)n—, R—O—(CH2)pO—, R—O—(CH2)p—S—, R—S—(CH2)n—, R—O—(CH2)n—(C═O)—(CH2)q—(O)m—, R—O—(CH2)n—(C═O)—(CH2)q—(S)m—, R—S—(CH2)p—O—, R—S—(CH2)p—S—, R—S—(C═S)—(S)m—, R—O—(C═S)—(O)m—, R—S—(CH2)n—(C═O)—(O)m—, R—O—(C═S)—(S)m—, R—S—(C═O)—(S)m—, R—S—(C═S)—(O)m—, R—S—(C═S)—(CH2)q—, R—O—(C═S)—(CH2)q—, R—S—(C═O)—(CH2)q—, R—S—(CH2)n—(C═S)—, R—O—(CH2)n—(C═S)—, R—S—(CH2)n—(C═O)—, R—(C═O)—(CH2)n—, R—(C═S)—, R—(C═O)—(CH2)n—O—(CH2)q—, R—(C═S)—S—, R—(C═O)—S—, R—(C═S)—O—, R—SO—(CH2)n—, R—SO2—(CH2)n—(O)m—, R—SO2—(CH2)n—(NR3)m—, R1R2N—(CH2)n—, R1R2N—O—, R1R2N—(C═O)—(CH2)q—(O)m—, R1R2N—(C═O)—(S)m—, R1R2N—(C═O)—(NR3)m—, R1R2N—(CH2)n—SO2—(CH2)q—(O)m—, R1R2N—(CH2)p—(C═O)—, R1R2N—(CH2)p—O—, R1R2N—O—(CH2)p, R1R2P(O)—, R1R2R3SiO—, R1R2R3Si—, R1R2R3Si—CH═CH, R1R2C═N—, R1R2C═N—O—, and R1R2C═N—NH—;m is 0 or 1, n and q are each independently an integer from 0 to 4, p is an integer from 1 to 4;R is hydrogen, a halogen-containing or not containing group selected from C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, C3˜C8 cycloalkenyl, and C3˜C6 cycloalkyl-C1˜C6 alkyl, aryl, aryl-C1˜C6 alkyl, heteroaryl, or heteroaryl-C1˜C6 alkyl, each of said aryl, aryl-C1˜C6 alkyl, heteroaryl, or heteroaryl-C1˜C6 alkyl is unsubstituted or substituted with 1˜3 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C6 alkyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C1˜C6 alkoxy, C1˜C6 alkylcarbonyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfonyl, C1˜C8 alkylamino, and C1˜C6 alkylcarbonyloxy;R1, R2, R3 are each independently is hydrogen, nitro, hydroxy, amino, a halogen-containing or not containing group selected from C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C8 alkynyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C1˜C6 alkoxy, C2˜C6 alkenyloxy, C2˜C6 alkynyloxy, C3˜C6 cycloalkyloxy, C1˜C6 alkoxy-C1˜C6 alkyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfanylcarbonyl, C1˜C6 alkylsulfonyl, C1˜C8 alkylsulfonyl-C1˜C6 alkyl, C1˜C6 alkylcarbonyl, C1˜C6 alkylcarbonyl-C1˜C8 alkyl, C1˜C6 alkylcarbonyloxy, C1˜C8 alkylamino, C1˜C6 alkylaminocarbonyl, C1˜C6 alkoxyaminocarbonyl, C1˜C6 alkoxycarbonyl-C1˜C8 alkyl, C1˜C6 alkylaminocarbonyl-C1˜C6 alkyl, triC1˜C6 alkylsilyl, and diC1˜C6 alkylphosphonyl, aryl, aryl-C1˜C6 alkyl, aryloxy, aryl-C1˜C6 alkyloxy, aryloxy-C1˜C6 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1˜C8 alkyl, heteroaryloxy, heteroaryl-C1˜C6 alkyloxy, heteroaryloxy-C1˜C6 alkyl, heteroarylcarbonyl, heteroarylsulfonyl, aliphatic heterocyclyl, aliphatic heterocyclyl-C1˜C6 alkyl, aliphatic heterocyclyloxy, aliphatic heterocyclyl-C1˜C6 alkyloxy, aliphatic heterocyclyloxy-C1˜C6 alkyl, aliphatic heterocyclylcarbonyl, or aliphatic heterocyclylsulfonyl, each of said aryl, aryl-C1˜C6 alkyl, aryloxy, aryl-C1˜C6 alkyloxy, aryloxy-C1˜C6 alkyl, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1˜C6 alkyl, heteroaryloxy, heteroaryl-C1˜C6 alkyloxy, heteroaryloxy-C1˜C8 alkyl, heteroarylcarbonyl, heteroarylsulfonyl, aliphatic heterocyclyl, aliphatic heterocyclyl-C1˜C6 alkyl, aliphatic heterocyclyloxy, aliphatic heterocyclyl-C1˜C8 alkyloxy, aliphatic heterocyclyloxy-C1˜C6 alkyl, aliphatic heterocyclylcarbonyl, or aliphatic heterocyclylsulfonyl is unsubstituted or substituted with 1˜3 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜CS alkyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C1˜C6 alkoxy, C1˜C6 alkylcarbonyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylamino, and C1˜C6 alkylcarbonyloxy; or R1R2N— is
  • 4. The pyridazinol compound or a derivative thereof according to claim 1, wherein, X is halogenated C1˜C6 alkyl;A is selected from the group consisting of C1˜C6 alkyl, C2˜C6 alkenyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, 5- to 14-membered aryl, 5- to 14-membered heteroaryl, and 5- to 14-membered aliphatic heterocyclyl, each of which is unsubstituted or substituted; wherein,when being substituted, said C1˜C6 alkyl, C2˜C6 alkenyl, C3˜C6 cycloalkyl, or C3˜C6 cycloalkenyl is substituted with one or more substituents independently selected from R—O—(CH2)n—(C═O)— and R1R2R3SiO—;when being substituted, said 5- to 14-membered aryl, 5- to 14-membered heteroaryl or 5- to 14-membered aliphatic heterocyclyl is substituted with one or more substituents independently selected from the group consisting of halogen, cyano, nitro, azido, a halogen-containing or not containing group selected from C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C8 cycloalkyl, and C3˜C6 cycloalkyl-C1˜C6 alkyl, aryl, aryl-C1˜C6 alkyl, heteroaryl, heteroaryl-C1˜C6 alkyl, aliphatic heterocyclyl, aliphatic heterocyclyl-C1˜C6 alkyl, each of said aryl, aryl-C1˜C8 alkyl, heteroaryl, heteroaryl-C1˜C6 alkyl, aliphatic heterocyclyl, or aliphatic heterocyclyl-C1˜C6 alkyl is unsubstituted or substituted with 1-5 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C6 alkyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C1˜C8 alkoxy, C1˜C6 alkylcarbonyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylsulfonyl, C1˜C6 alkylamino, and C1˜C6 alkylcarbonyloxy, R—O—(CH2)n—, R—O—(CH2)p—O—, R—S—(CH2)n—, R—O—(CH2)n—(C═O)—(CH2)q—(O)m—, R—O—(CH2)n—(C═O)—(CH2)q—(S)m—, R—S—(CH2)n—(C═O)—, R—(C═O)—(CH2)n—, R—(C═O)—(CH2)n—O—(CH2)q—, R—SO—(CH2)n—, R—SO2—(CH2)n—(O)m—, R—SO2—(CH2)n—(NR3)m—, R1R2N—(C═O)—(CH2)q—(O)m—, R1R2N—(C═O)—(NR3)m—, R1R2N—(CH2)n—, R1R2N—(CH2)n—SO2—(CH2)q—, R1R2P(O)—, and R1R2R3Si—;m is 0 or 1, n and q are each independently an integer from 0 to 4, p is an integer from 1 to 4;R is hydrogen, a halogen-containing or not containing group selected from C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, and C3˜C6 cycloalkyl-C1˜C6 alkyl, 5- to 14-membered aryl, 5- to 14-membered aryl-C1˜C4 alkyl, or 5- to 14-membered heteroaryl, each of said 5- to 14-membered aryl, 5- to 14-membered aryl-C1˜C4 alkyl, or 5- to 14-membered heteroaryl is unsubstituted or substituted with 1˜3 groups independently selected from halogens;R1, R2, R3 are each independently hydrogen, nitro, hydroxy, amino, a halogen-containing or not containing group selected from C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, C1˜C6 alkoxy, C1˜C6 alkoxy-C1˜C6 alkyl, C1˜C6 alkoxycarbonyl, C1˜C6 alkylcarbonyl, C1˜C6 alkylcarbonyl-C1˜C6 alkyl, and C1˜C6 alkylcarbonyloxy, 5- to 14-membered aryl, 5- to 14-membered aryl-C1˜C6 alkyl, 5- to 14-membered aryloxy, 5- to 14-membered arylcarbonyl, 5- to 14-membered heteroaryl, 5- to 14-membered heteroaryl-C1˜C6 alkyl, 5- to 14-membered heteroaryloxy, 5- to 14-membered heteroarylcarbonyl, or 5- to 14-membered aliphatic heterocyclylcarbonyl, each of said 5- to 14-membered aryl, 5- to 14-membered aryl-C1˜C6 alkyl, 5- to 14-membered aryloxy, 5- to 14-membered arylcarbonyl, 5- to 14-membered heteroaryl, 5- to 14-membered heteroaryl-C1˜C6 alkyl, 5- to 14-membered heteroaryloxy, 5- to 14-membered heteroarylcarbonyl, or 5- to 14-membered aliphatic heterocyclylcarbonyl is unsubstituted or substituted with 1˜3 groups independently selected from halogen, cyano, nitro, hydroxy, carboxyl, sulfhydryl, amino, and a halogen-containing or not containing group selected from C1˜C6 alkyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkyl-C1˜C6 alkyl, C2˜C6 alkenyl, C2˜C6 alkynyl, C1˜C6 alkoxy, C1˜C6 alkylcarbonyl, C1˜C8 alkoxycarbonyl, C1˜C8 alkylsulfonyl, C1˜C6 alkylamino, and C1˜C8 alkylcarbonyloxy; or R1R2N— is
  • 5. The pyridazinol compound or a derivative thereof according to claim 1, wherein, X is halogenated C1˜C4 alkyl;A is selected from the group consisting of C1˜C4 alkyl, C2˜C4 alkenyl, C3˜C6 cycloalkyl, C3˜C6 cycloalkenyl, 5- to 14-membered aryl, 5- to 14-membered heteroaryl and 5- to 14-membered aliphatic heterocyclyl, each of which is unsubstituted or substituted; wherein,when being substituted, said C1˜C4 alkyl, C2˜C4 alkenyl, C3˜C6 cycloalkyl, or C3˜C6 cycloalkenyl is substituted with one or more substituents independently selected from R—O—(C═O)— and R1R2R3SiO—;when being substituted, said 5- to 14-membered aryl, 5- to 14-membered heteroaryl or 5- to 14-membered aliphatic heterocyclyl is substituted with one or more substituents independently selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, nitro, azido, a fluoro-, chloro- or bromo-containing or not containing group selected from C1˜C4 alkyl, C2˜C4 alkenyl, C2˜C4 alkynyl, C3˜C6 cycloalkyl, and C3˜C6 cycloalkyl-C1˜C4 alkyl, aryl, aryl-C1˜C4 alkyl, heteroaryl, heteroaryl-C1˜C4 alkyl, aliphatic heterocyclyl, each of said aryl, aryl-C1˜C4 alkyl, heteroaryl, heteroaryl-C1˜C4 alkyl, or aliphatic heterocyclyl is unsubstituted or substituted with 1˜3 groups independently selected from fluorine, chlorine, bromine, cyano, hydroxy, and a fluoro-, chloro- or bromo-containing or not containing group selected from C1˜C4 alkyl, C1˜C4 alkoxy, C1˜C4 alkoxycarbonyl, C1˜C4 alkylsulfonyl, and C1˜C4 alkylamino, R—O—(CH2)n—, R—O—CH2—O—, R—S—(CH2)n—, R—O—(CH2)n—(C═O)—, R—O—(CH2)n—(C═O)—O—, R—O—(C═O)—(CH2)q—O—, R—O—(CH2)n—(C═O)—(CH2)q—S—, R—S—(CH2)n—(C═O)—, R—(C═O)—(CH2)n—, R—(C═O)—O—(CH2)q—, R—(C═O)—(CH2)n—O—, R—SO—(CH2)n—, R—SO2—(CH2)n—(O)m—, R—SO2—(CH2)n—NR3—, R1R2N—(C═O)—(CH2)q—, R1R2N—(C═O)—(CH2)q—O—, R1R2N—(C™0)(NR3)m—, R1R2N—(CH2)n—, R1R2N—(CH2)n—SO2—(CH2)q—, R1R2P(O), and R1R2R3Si—;m is 0 or 1, n and q are each independently an integer from 0, 1, 2 and 3, p is an integer from 1, 2 and 3;R is hydrogen, a halogen-containing or not containing group selected from C1˜C4 alkyl, C2˜C4 alkenyl, C2˜C6 alkynyl, C3˜C6 cycloalkyl, and C3˜C6 cycloalkyl-C1˜C4 alkyl, 5- to 14-membered aryl, 5- to 14-membered aryl-C1˜C2 alkyl, or 5- to 6-membered heteroaryl, each of said 5- to 14-membered aryl, 5- to 14-membered aryl-C1˜C2 alkyl, or 5- to 6-membered heteroaryl is unsubstituted or substituted with 1˜3 groups independently selected from fluorine, chlorine, and bromine;R1, R2, R3 are each independently hydrogen, a fluoro-, chloro- or bromo-containing or not containing group selected from C1˜C4 alkyl, C2˜C4 alkenyl, C2˜C4 alkynyl, C3˜C6 cycloalkyl, C1˜C4 alkoxy, C1˜C4 alkoxyC1˜C4 alkyl, C1˜C4 alkoxycarbonyl, C1˜C4 alkylcarbonyl, C1˜C4 alkylcarbonyl-C1˜C4 alkyl, and C1˜C4 alkylcarbonyloxy, 5- to 14-membered aryl, 5- to 14-membered aryloxy, 5- to 14-membered arylcarbonyl, 5- to 6-membered heteroaryl, 5- to 6-membered heteroaryl-C1˜C4 alkyl, or 5- to 6-membered heteroarylcarbonyl, each of said 5- to 14-membered aryl, 5- to 14-membered aryloxy, 5- to 14-membered arylcarbonyl, 5- to 6-membered heteroaryl, 5- to 6-membered heteroaryl-C1˜C4 alkyl, or 5- to 6-membered heteroarylcarbonyl is unsubstituted or substituted with 1˜3 groups independently selected from fluorine, chlorine, bromine, C1˜C4 alkyl, C1˜C4 alkoxy, C1˜C4 alkylamino, and C3˜C6 cycloalkyl; or R1R2N— is
  • 6. The pyridazinol compound or a derivative thereof according to claim 1, wherein, X is CH2F, CHF2, CF3, or CF2CF3;A is methyl, ethyl,
  • 7. The pyridazinol compound or a derivative thereof according to claim 1, wherein, the compound is selected from those of Formula I, wherein X and A are shown below:
  • 8. The derivative of the pyridazinol compound according to claim 1, which has a structure as shown in Formula I-1:
  • 9. The derivative of the pyridazinol compound according to claim 8, wherein the pyridazinol compound is selected from the compounds having a structure of
  • 10. A method for preparing a pyridazinol compound or a derivative thereof according to claim 1, comprising: (1) subjecting a compound of Formula II and a compound of Formula III to Suzuki reaction to obtain a compound of Formula IV;(2) hydrolyzing the compound of Formula IV to obtain a compound of Formula I;wherein the reaction route is as follows:
  • 11. The method according to claim 10, wherein, each of the steps independently is carried out at a temperature in the range from 20 to 150° C.; wherein steps (1) and (b) are carried out in the presence of a catalyst, a base and a solvent, wherein the catalyst is Pd(dppf)Cl2CH2Cl2, Pd(dba)2, Pd2(dba)3, Pd(PPh3)4, PdCl2, Pd(OAc)2, Pd(dppf)Cl2, Pd(PPh3)2Cl1, or Ni(dppf)Cl2, the base is one or more selected from Et3N, NaHCO3, KOAc, K2CO3, K3PO4, Na2CO3, CsF, Cs2CO3, t-BuONa, EtONa, KOH, and NaOH, and the solvent is THF/water, toluene/water, DMF/water, 1,4-dioxane/water, toluene/ethanol/water, acetonitrile/water, THF, toluene, 1,4-dioxane, acetonitrile, or DMF system;steps (2) and (a) are carried out in the presence of a base and a solvent or in the presence of a solution of boron tribromide, a solution of hydrobromic acid in acetic acid, a solution of hydrochloric acid in methanol or a solution of hydrochloric acid in ethyl acetate, wherein the base is selected from NaOH, KOH, potassium acetate, and sodium acetate, and the solvent is water or DMSO.
  • 12. A method for preparing a derivative of a pyridazinol compound according to claim 8, wherein, when the derivative is an ester or ether derivative, the reaction route is as follows:
  • 13. The method according to claim 11, wherein the reactions for preparing the ester and ether derivatives and the second step for preparing the oxime and hydroxylamine derivatives are carried out in the presence of a base and a solvent, wherein the base is one or more selected from the group consisting of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, cesium carbonate, triethylamine and diisopropylethylamine; the solvent is THF, 1,4-dioxane, toluene, 1,2-dichloroethane, ethyl acetate, acetonitrile, DMF, acetone, dichloromethane, or chloroform; the first step for preparing the oxime and hydroxylamine derivative is carried out in the presence of a halogenation reagent and a solvent, wherein the halogenation reagent is phenofluor/cesium fluoride or POCl3, and the solvent is one or more selected from the group consisting of toluene, 1,2-dichloroethane, and DMF; and the reaction temperature is in the range of 0 to 120° C.
  • 14. A herbicidal composition, comprising at least one compound chosen from the pyridazinol compound of Formula I and the derivative thereof according to claim 1.
  • 15-18. (canceled)
  • 19. A herbicidal composition, comprising at least one compound chosen from the derivative of the pyridazinol of Formula I-1 according to claim 8.
  • 20. The herbicidal composition according to claim 14, further comprising at least one additional herbicide.
  • 21. The herbicidal composition according to claim 19, further comprising at least one additional herbicide
  • 22. The herbicidal composition according to claim 20, wherein the at least one additional herbicide is selected from an HPPD inhibitor, a hormone herbicide, and a PDS inhibitor.
  • 23. A method for controlling a harmful plant, comprising applying a herbicidally effective amount of at least one compound selected from the pyridazinol compound and the derivative thereof according to claim 1 to the harmful plant or an area with the harmful plant.
  • 24. A method for controlling a harmful plant, comprising applying a herbicidally effective amount of at least one compound selected from the derivative of pyridazinol compound according to claim 8 to the harmful plant or an area with the harmful plant.
  • 25. A method for controlling a harmful plant in a useful crop, comprising applying a herbicidally effective amount of at least one compound selected from the pyridazinol compound and the derivative thereof according to claim 1 to the harmful plant, wherein the useful crop is selected from wheat, corn, rice, soybean, cotton, oilseed rape, millet and sorghum.
  • 26. A method for controlling a harmful plant in a useful crop, comprising applying a herbicidally effective amount of at least one compound selected from the derivative of pyridazinol compound according to claim 8 to the harmful plant, wherein the useful crop is selected from wheat, corn, rice, soybean, cotton, oilseed rape, millet and sorghum.
  • 27. The method according to claim 24, wherein the harmful plant is a monocotyledonous or dicotyledonous harmful plant, selected from Amaranthus retroflexus, Rorippa indica, Veronica polita, Chenopodiaceae, Echinochloa crus-galli, Setaria viridis, Galium aparine, Abutilon mill, Sisymbrium sophia and Galinsoga parviflora.
  • 28. The method according to claim 25, wherein the harmful plant is a monocotyledonous or dicotyledonous harmful plant, selected from Amaranthus retroflexus, Rorippa indica, Veronica polita, Chenopodiaceae, Echinochloa crus-galli, Setaria viridis, Galium aparine, Abutilon mill, Sisymbrium sophia and Galinsoga parviflora.
Priority Claims (2)
Number Date Country Kind
201810104963.4 Feb 2018 CN national
201811035352.5 Sep 2018 CN national
PCT Information
Filing Document Filing Date Country Kind
PCT/CN2019/074315 2/1/2019 WO