WO2023051261A1 - Imine compound and use thereof - Google Patents

Imine compound and use thereof Download PDF

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Publication number
WO2023051261A1
WO2023051261A1 PCT/CN2022/118920 CN2022118920W WO2023051261A1 WO 2023051261 A1 WO2023051261 A1 WO 2023051261A1 CN 2022118920 W CN2022118920 W CN 2022118920W WO 2023051261 A1 WO2023051261 A1 WO 2023051261A1
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sch
alkyl
haloalkyl
phenyl
halogen
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PCT/CN2022/118920
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French (fr)
Chinese (zh)
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吴鸿飞
徐靖博
孙俊
韩金龙
刘少武
解喜山
郭春晓
徐利保
程学明
于海波
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沈阳中化农药化工研发有限公司
江苏扬农化工股份有限公司
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Publication of WO2023051261A1 publication Critical patent/WO2023051261A1/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/02—Acaricides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/04—Insecticides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/56—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/40—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/02—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by halogen atoms, e.g. imino-halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Definitions

  • the invention belongs to the field of insecticides and acaricides, and in particular relates to an imine compound and its application.
  • WO2005073165A1 and WO2010018714A1 disclose bisamide structure type compounds with insecticidal activity.
  • the imine structure type compound of the present invention has a novel structure and has excellent insecticidal and acaricidal activities.
  • the imine compounds shown in the present invention and their insecticidal and acaricidal activities have not been reported.
  • the object of the present invention is to provide an imine compound and its application as an insecticide or acaricide.
  • a kind of imine compound the structure of imine compound is shown in general formula I:
  • X 1 is selected from halogen, nitro, cyano, CONH 2 , CHO, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl , C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylamino, C 1 -C 6 dialkylamino, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkyl Carbonyl, C 1 -C 6 Alkylsulfonyl, C 1 -C 6 Haloalkylsulfonyl, C 1
  • n is selected from 0, 1, 2, 3, 4 or 5;
  • X 2 and X 3 can be the same or different and are selected from H, halogen, nitro, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 - C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl;
  • R 1 is selected from H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or cyano methylene;
  • R 2 is selected from H, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkylamine C 1 -C 6 haloalkylamino group, C 1 -C 6 dialkylamino group, C 1 -C 6 halodialkylamino group, C 1 -C 6 alkoxy group , C 1 -C 6 Haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 2 -C 6 haloalkynyloxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 2 -C 6 alkenylthio, C 2 -C 6 haloalkenylthio, C 2 -
  • Y 1 and Y 2 may be the same or different and are selected from halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio or C 1 -C 6 haloalkylthio.
  • X 1 is selected from halogen, nitro, cyano, CONH 2 , CHO, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl , C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, C 1 -C 3 alkylamino, C 1 -C 3 dialkylamino, C 1 -C 3 alkoxycarbonyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkyl Carbonyl, C 1 -C 3 Alkylsulfonyl, C 1 -C 3 Haloalkylsulfonyl, C 1
  • n is selected from 0, 1, 2, 3, 4 or 5;
  • X 2 and X 3 may be the same or different and are selected from H, halogen, nitro, cyano, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 4 alkenyl, C 2 - C 4 haloalkenyl, C 2 -C 4 alkynyl or C 2 -C 4 haloalkynyl;
  • R 1 is selected from H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or cyano methylene;
  • R 2 is selected from H, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 4 alkenyl, halogenated C 2 -C 4 alkenyl, C 1 -C 3 alkylamine C 1 -C 3 haloalkylamino, C 1 -C 3 dialkylamino, C 1 -C 3 halodialkylamino, C 1 -C 3 alkoxy , C 1 -C 3 Haloalkyloxy, C 2 -C 4 alkenyloxy, C 2 -C 4 haloalkenyloxy, C 2 -C 4 alkynyloxy, C 2 -C 4 haloalkynyloxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, C 2 -C 4 alkenylthio, C 2 -C 4 haloalkenylthio, C 2 -C 4
  • Y 1 and Y 2 may be the same or different and are selected from halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio or C 1 -C 3 haloalkylthio.
  • X 1 is selected from halogen, nitro, cyano, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy or C 1 -C 3 haloalkylthio;
  • n 0, 1, 2 or 3;
  • X 2 and X 3 can be the same or different and are independently selected from H or halogen;
  • R 1 is selected from H or C 1 -C 3 alkyl
  • R 2 is selected from halogen, C 1 -C 3 alkylamino, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, 1-1H-1,2,4-triazolyl or 4 Piperazin-1-yl substituted by the following groups, wherein the following groups are: C 1 -C 3 alkyl, C 1 -C 3 alkylcarbonyl or phenyl;
  • Y 1 and Y 2 may be the same or different and are selected from halogen, C 1 -C 3 haloalkyl or C 1 -C 3 haloalkoxy.
  • X is selected from F, Cl, Br, I, nitro, cyano, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy or trifluoromethylthio;
  • n is selected from 0, 1 or 2;
  • Both X2 and X3 are selected from F;
  • R is selected from H or methyl
  • R is selected from F, Cl, Br, I, methylamino, ethylamino, propylamino, cyclopropanylamino, methoxy, ethoxy, propoxy, methylthio, ethylthio, propyl Thio, 1-1H-1,2,4-triazolyl or 4-methylpiperazin-1-yl, 4-ethylpiperazin-1-yl, 4-acetylpiperazin-1-yl , 4-phenylpiperazin-1-yl;
  • Y1 and Y2 may be the same or different and are selected from F, Cl, Br, I, trifluoromethyl, trifluoromethoxy or difluoromethoxy.
  • X is selected from F, Cl, nitro, cyano, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy or trifluoromethylthio;
  • n is selected from 0, 1 or 2;
  • Both X2 and X3 are selected from F;
  • R 1 is selected from methyl
  • R is selected from Cl, Br, methylamino, ethoxy, methylthio, ethylthio, 1-1H-1,2,4-triazolyl or 4-ethylpiperazin-1-yl;
  • Y 1 and Y 2 may be the same or different and are selected from Br, trifluoromethyl or difluoromethoxy.
  • R 2 is H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxy Methylene, C 1 -C 6 haloalkoxymethylene, C 1 -C 6 alkylthiomethylene, C 1 -C 6 haloalkylthiomethylene, C 1 -C 6 alkylaminomethylene C 1 -C 6 haloalkylaminomethylene, C 1 -C 6 dialkylaminomethylene, C 1 -C 6 halodialkylaminomethylene, phenyl or cyanomethylene )
  • the specific synthesis method is as follows, the compound of general formula IV reacts with an acid chloride reagent (such as oxalyl chloride and thionyl chloride, etc.) to prepare acid chloride III, the compound of acid chloride III reacts with the compound of general formula V-a to prepare the compound of general formula II, and the compound of general formula II and substituted aniline
  • an acid chloride reagent such as oxalyl chloride and thionyl chloride, etc.
  • the specific synthesis method is as follows, the compound of general formula VIII reacts with an acid chloride reagent (such as oxalyl chloride and thionyl chloride, etc.) to prepare acid chloride VII, the reaction of acid chloride VII and substituted aniline V prepares a compound of general formula VI, and the compound of general formula VI reacts with a halogenating reagent (such as phosphorus oxychloride and phosphorus oxybromide, etc.) dehydration reaction to prepare imines, that is, compounds of general formula I.
  • an acid chloride reagent such as oxalyl chloride and thionyl chloride, etc.
  • a halogenating reagent Such as phosphorus oxychloride and phosphorus oxybromide, etc.
  • the specific synthesis method is as follows, 2-fluoro-3-nitrobenzoic acid reacts with acyl chloride reagents (such as oxalyl chloride and thionyl chloride, etc.) to prepare 2-fluoro-3-nitrobenzoyl chloride, 2-fluoro-3- The reaction of nitrobenzoyl chloride and substituted aniline V to prepare the compound of general formula XI, the reduction reaction of the nitro group of the compound of general formula XI to prepare the compound of general formula X, the alkylation reaction of the compound of general formula X to prepare the compound of general formula IX, the compound of general formula IX and acid chloride III reaction to prepare the compound of general formula VI, the dehydration reaction of the compound of general formula VI with a halogenation reagent (such as phosphorus oxychloride and phosphorus oxybromide, etc.) to prepare imine, that is, the compound of general formula I.
  • acyl chloride reagents such as ox
  • R 2 is C 1 -C 6 alkylamino group, C 1 -C 6 haloalkylamino group, C 1 -C 6 dialkylamino group, C 1 -C 6 halodialkylamino group, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 2 -C 6 haloalkynyloxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 2 -C 6 alkenylthio, C 2 -C 6 haloalkenylthio Base, C 2 -C 6 alkynylthio, C 2 -C 6 haloalkynylthio, amino, hydrazino, cyano, 1-pyrrolidinyl, 1-piperidin
  • the specific synthesis method is as follows, the compound of general formula VI is reacted with phosphorus oxybromide to prepare the compound of general formula I-a, and the compound of general formula I-a is further substituted to prepare the compound of general formula I.
  • Intermediate V, intermediate V-1 and intermediate X can be prepared according to the method of US8853440B2.
  • Acid halide reagents other conventional raw materials and reagents are usually commercially available, and can also be self-made according to conventional methods.
  • Halogen refers to fluorine, chlorine, bromine or iodine.
  • Alkyl linear, branched or cyclic alkyl, such as methyl, ethyl, n-propyl, isopropyl or cyclopropyl, etc.
  • Haloalkyl Straight chain, branched or cyclic alkyl, the hydrogen atoms on these alkyl groups can be partially or completely replaced by halogen, such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, Difluoromethyl, trifluoromethyl, pentafluoroethyl or heptafluoroisopropyl, etc.
  • halogen such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, Difluoromethyl, trifluoromethyl, pentafluoroethyl or heptafluoroisopropyl, etc.
  • Alkenyl straight-chain, branched or cyclic alkenyl groups such as vinyl, 1-propenyl, 2-propenyl and the different butenyl, pentenyl and hexenyl isomers; alkenyl also includes polyenes Classes such as 1,2-propadienyl and 2,4-hexadienyl, etc.
  • Haloalkenyl an alkenyl group in which at least one or more hydrogen atoms may be replaced by a halogen atom.
  • Alkynyl includes straight or branched chain alkynyl groups such as ethynyl, 1-propynyl and the different butynyl, pentynyl and hexynyl isomers; alkynyl also includes radicals consisting of multiple triple bonds group, such as 2,5-hexadiynyl.
  • Haloalkynyl an alkynyl group in which at least one or more hydrogen atoms may be replaced by halogen atoms.
  • Alkoxy linear, branched or cyclic alkoxy, such as methoxy, ethoxy, n-propoxy, isopropoxy, cyclopropyloxy or n-butoxy, etc.
  • Halogenated alkoxy straight chain, branched or cyclic alkoxy, the hydrogen atoms on these alkoxy can be partially or completely replaced by halogen, such as chloromethoxy, dichloromethoxy, trichloromethoxy fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy, heptafluoroisopropyloxy, etc.
  • halogen such as chloromethoxy, dichloromethoxy, trichloromethoxy fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy, heptafluoroisopropyloxy, etc.
  • Alkylthio Straight-chain, branched or cyclic alkyl, bonded to the structure via a sulfur atom, such as methylthio, ethylthio, etc.
  • Halogenated alkylthio straight chain, branched or cyclic alkylthio, the hydrogen atoms on these alkylthio can be partially or completely replaced by halogen, such as difluoromethylthio, trifluoroethylthio, etc.
  • Alkenylthio straight-chain, branched-chain or cyclic alkenyl, bonded to the structure via a sulfur atom, such as 1-propenyl-3-thio, 2-butenyl-4-thio, etc.
  • Haloalkenylthio straight-chain, branched or cyclic alkenylthio, the hydrogen atoms on these alkenylthio can be partially or fully replaced by halogen.
  • Alkynylthio straight-chain, branched-chain or cyclic alkynyl, bonded to the structure via a sulfur atom, such as 1-propynyl-3-thio, 2-butynyl-4-thio, etc.
  • Haloalkynylthio Straight-chain, branched or cyclic alkynylthio. The hydrogen atoms on these alkynylthio groups can be partially or completely replaced by halogen.
  • Alkylamino Straight-chain, branched-chain, or cyclic alkyl group bonded to the structure via a nitrogen atom bond, such as methylamino, ethylamino, n-propylamino, isopropylamino, or isomeric butyl Amino.
  • Dialkylamino Two identical or different straight-chain, branched-chain or cyclic alkyl groups linked to the structure via a nitrogen atom bond, such as dimethylamino, methylethylamino, dicyclopropylamino, etc.
  • Alkoxycarbonyl alkyl-O-CO-, eg CH 3 OCO-.
  • Alkylcarbonyl alkyl-CO-, such as CH3CO-
  • Alkylsulfonyl alkyl-S(O) 2 -, such as methylsulfonyl.
  • Alkylsulfinyl alkyl-S(O)-, eg methylsulfinyl.
  • Alkylaminocarbonyl alkyl-NH-CO-, eg CH 3 NHCO-.
  • Alkylaminosulfonyl alkyl-NH-S(O) 2 -, eg CH 3 NHS(O) 2 -.
  • the compound of general formula I is a chirality structure compound.
  • the compound can be mixed with a single chiral isomer or two chiral isomers Existing in different forms; the imine structure of the compound of general formula I has geometric isomerism, and the compound can exist in the form of a single geometric isomer or a mixture of two geometric isomers.
  • the compound shown in the general formula I to be protected by the present invention is not protected by the above Isomer structures exist as formal limitations.
  • the novel imine derivatives (compound of general formula I) of the present invention have excellent insecticidal and acaricidal activities, and can control the following pests: Lepidoptera pests, such as armyworm, beet armyworm and diamondback moth, etc.; Homoptera Pests, such as green peach aphid, leaf-chan and planthopper, etc.; Hemiptera pests, such as corn long bug, tomato mirid bug and rice ailanthus, etc.; Thysanoptera pests, such as cotton thrips, alfalfa thrips and soybean thrips, Western Flower thrips, etc.; Coleoptera pests, such as potato beetles and clam beetles; Diptera pests, such as flies and mosquitoes; Hymenoptera pests, such as bees and ants.
  • Lepidoptera pests such as armyworm, beet armyworm and diamondback moth, etc.
  • Homoptera Pests
  • the present invention also includes the use of the compound of general formula I for controlling insect pests and acarids in the fields of agriculture, forestry and hygiene.
  • the technical scheme of the present invention also includes a method for controlling pests: applying the pesticidal compound of the present invention to the pests or their growth medium.
  • the more suitable effective dose is 10 grams to 1000 grams per hectare, and the preferred effective dose is 20 grams to 500 grams per hectare.
  • the technical solution of the present invention also includes a method for controlling harmful mites: applying the insecticidal compound of the present invention to the harmful mites or their growth medium.
  • the more suitable effective dose is 10 grams to 1000 grams per hectare, and the preferred effective dose is 20 grams to 500 grams per hectare.
  • the compound of the invention is novel in structure, has both insecticidal and acaricidal properties, and has wide uses.
  • Embodiment 1 the preparation of compound I-38
  • reaction solution was lowered to room temperature, filtered to remove insoluble matter, added ethyl acetate (100mL) to dissolve, washed with saturated aqueous sodium bicarbonate solution and saturated brine successively, separated the organic phase, dried the organic phase with anhydrous magnesium sulfate, filtered Afterwards, the organic solvent was evaporated under reduced pressure, and the residue was separated and purified by column chromatography to obtain the title product, 1.86 g of a white solid, with a yield of 8% (with 2-bromo-4-heptafluoroisopropyl-6-trifluoromethylaniline count).
  • reaction system was cooled to room temperature, and the reaction solution was slowly poured into ice water (20 mL), fully stirred, and a solid was precipitated, filtered, and the filter cake was separated and purified by column chromatography to obtain the title product, 1.02 g of a white solid, and the yield was 90% ( N-(2-bromo-4-heptafluoroisopropyl-6-trifluoromethylphenyl)-2-fluoro-3-aminobenzamide).
  • the reaction system was cooled to room temperature, fully stirred, and the solid was gradually precipitated, filtered, and the filter cake was separated and purified by column chromatography to obtain the title product, 0.57 g of a white solid, and the yield was 85% (based on N-(2-bromo-4-heptafluoro (isopropyl-6-trifluoromethylphenyl)-2-fluoro-3-methylaminobenzamide).
  • reaction system was cooled to room temperature, the reaction solution was slowly poured into a large amount of ice water, fully stirred, dissolved with ethyl acetate (30mL), extracted, and layered, the organic phase was washed successively with saturated aqueous sodium bicarbonate and saturated brine, and separated The organic phase was taken out, and the organic phase was dried with anhydrous magnesium sulfate.
  • Embodiment 2 the preparation of compound I-46
  • Embodiment 3 the preparation of compound I-122
  • reaction system was cooled to room temperature, the reaction solution was slowly poured into a large amount of ice water, fully stirred, dissolved with ethyl acetate (30mL), extracted, and layered, the organic phase was washed successively with saturated aqueous sodium bicarbonate and saturated brine, and separated The organic phase was taken out, and the organic phase was dried with anhydrous magnesium sulfate.
  • Embodiment 4 the preparation of compound I-128
  • reaction system was cooled to room temperature, the reaction solution was slowly poured into a large amount of ice water, fully stirred, dissolved with ethyl acetate (30mL), extracted, and layered, the organic phase was washed successively with saturated aqueous sodium bicarbonate and saturated brine, and separated The organic phase was taken out, and the organic phase was dried with anhydrous magnesium sulfate.
  • Embodiment 5 the preparation of compound I-130
  • reaction system was cooled to room temperature, the reaction solution was slowly poured into a large amount of ice water, fully stirred, dissolved with ethyl acetate (30mL), extracted, and layered, the organic phase was washed successively with saturated aqueous sodium bicarbonate and saturated brine, and separated The organic phase was taken out, and the organic phase was dried with anhydrous magnesium sulfate.
  • Embodiment 6 the preparation of compound I-176
  • Embodiment 7 the preparation of compound I-618
  • Embodiment 8 the preparation of compound I-620
  • the system was lowered to room temperature, quenched with 1N hydrochloric acid, diluted with water, extracted with ethyl acetate, separated into layers, and the organic phase was washed with water and saturated brine successively, and separated The organic phase was taken out, dried with anhydrous magnesium sulfate, filtered, and the organic solvent was distilled off under reduced pressure. The residue was separated and purified by column chromatography to obtain the title compound, 95.5 mg of white solid, with a yield of 63%.
  • Embodiment 9 the preparation of compound I-626
  • the reaction system is cooled to room temperature, the reaction solution is poured into a large amount of water, extracted with ethyl acetate, layered, the organic phase is washed with water and saturated brine successively, and the organic phase is separated. phase, the organic phase was dried with anhydrous magnesium sulfate, filtered, and the organic solvent was distilled off under reduced pressure. The residue was separated and purified by column chromatography to obtain the title compound, 71.0 mg of white solid, with a yield of 48%.
  • Embodiment 10 the preparation of compound I-628
  • reaction system is lowered to room temperature, poured into a large amount of water, extracted with ethyl acetate, layered, organic phase Wash with water and saturated brine for several times, separate the organic phase, dry the organic phase with anhydrous magnesium sulfate, filter and distill off the organic solvent under reduced pressure, and the residue is separated and purified by column chromatography to obtain the title compound, white solid 122.3 mg, yield 85%.
  • Embodiment 11 the preparation of compound I-630
  • the reaction system was cooled to room temperature, and the reaction solution was poured into a large amount of water, extracted with ethyl acetate, layered, and the organic phase was washed with water and saturated brine successively , separated the organic phase, dried the organic phase with anhydrous magnesium sulfate, filtered and evaporated the organic solvent under reduced pressure, and the residue was separated and purified by column chromatography to obtain the title compound, 120.7 mg of white solid, with a yield of 76%.
  • Embodiment 12 Preparation of Compound I-632
  • solubility of the compound to be tested dissolve it with acetone or dimethyl sulfoxide, and then use 0.1% Tween 80 solution to prepare 50 ml of the test solution of the required concentration, acetone or dimethyl sulfoxide in the total solution content of not more than 10%, for use.
  • Select cabbage leaves cultivated at room temperature remove the waxy layer on the surface, use a puncher to make a circular leaf disc with a diameter of 2 cm, put it into the prepared medicinal solution and soak it for 10 seconds, dry it in the shade, and place it in a container with filter paper.
  • neat healthy test insects (2 instars) were inserted, and 10 insects were each treated. The test was repeated 4 times, and the water treatment was set as a blank control. After treatment, put them into a room with 24°C, 60%-70% relative humidity, and natural light for indoor cultivation. After 72 hours, investigate the number of surviving insects and calculate the mortality rate.
  • Embodiment 14 Determination of acaricidal activity

Abstract

The present invention belongs to the field of insecticides and acaricides, and specifically relates to an imine compound and the use thereof. The structure is as represented by general formula I, wherein each substituent in the formula is defined in the description. The compound of general formula I has excellent insecticidal and acaricidal activities, and can be used for preventing and controlling various pest insects or pest mites.

Description

一种亚胺类化合物及其应用A kind of imine compound and its application 技术领域technical field
本发明属于杀虫剂和杀螨剂领域，具体涉及一种亚胺类化合物及其应用。The invention belongs to the field of insecticides and acaricides, and in particular relates to an imine compound and its application.
背景技术Background technique
在农业和园艺等的作物生产中，由于害虫和害螨等引起的侵害依然显著以及害虫和害螨对现有杀虫剂和杀螨剂产生抗性，因此需要不断研发新型杀虫剂和杀螨剂，及其组合物。In crop production such as agriculture and horticulture, since damage caused by pests and pest mites is still significant and pests and pest mites develop resistance to existing insecticides and acaricides, research and development of new insecticides and Acaricide, and composition thereof.
WO2005073165A1和WO2010018714A1公开了具有杀虫活性的双酰胺结构类型化合物。WO2005073165A1 and WO2010018714A1 disclose bisamide structure type compounds with insecticidal activity.
为发现新型杀虫剂或杀螨剂，发明人经潜心研究发现本发明的亚胺结构类型化合物，如通式I所示，其结构新颖，并具有优异的杀虫和杀螨活性。本发明所示的亚胺类化合物及其杀虫和杀螨活性未见报道。In order to find new insecticides or acaricides, the inventors have devoted themselves to research and found that the imine structure type compound of the present invention, as shown in the general formula I, has a novel structure and has excellent insecticidal and acaricidal activities. The imine compounds shown in the present invention and their insecticidal and acaricidal activities have not been reported.
发明内容Contents of the invention
本发明的目的在于提供一种亚胺类化合物及其作为杀虫剂或杀螨剂的应用。The object of the present invention is to provide an imine compound and its application as an insecticide or acaricide.
为实现上述目的，本发明的技术方案如下：To achieve the above object, the technical scheme of the present invention is as follows:
一种亚胺类化合物：亚胺类化合物结构如通式I所示：A kind of imine compound: the structure of imine compound is shown in general formula I:
Figure PCTCN2022118920-appb-000001
Figure PCTCN2022118920-appb-000001
式中：In the formula:
Q选自
Figure PCTCN2022118920-appb-000002
Q from
Figure PCTCN2022118920-appb-000002
X 1选自卤素、硝基、氰基、CONH 2、CHO、C 1-C 6烷基、C 1-C 6卤代烷基、C 2-C 6烯基、C 2-C 6卤代烯基、C 2-C 6炔基、C 2-C 6卤代炔基、C 1-C 6烷氧基、C 1-C 6卤代烷氧基、C 1-C 6烷硫基、C 1-C 6卤代烷硫基、C 1-C 6烷基氨基、C 1-C 6二烷基氨基、C 1-C 6烷氧基羰基、C 1-C 6烷基羰基、C 1-C 6卤代烷基羰基、C 1-C 6烷基磺酰基、C 1-C 6卤代烷基磺酰基、C 1-C 6烷基亚磺酰基、C 1-C 6卤代烷基亚磺酰基、C 1-C 6烷基氨基羰基或C 1-C 6烷基氨基磺酰基； X 1 is selected from halogen, nitro, cyano, CONH 2 , CHO, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl , C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylamino, C 1 -C 6 dialkylamino, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkyl Carbonyl, C 1 -C 6 Alkylsulfonyl, C 1 -C 6 Haloalkylsulfonyl, C 1 -C 6 Alkylsulfinyl, C 1 -C 6 Haloalkylsulfinyl, C 1 -C 6 Alkane Aminocarbonyl or C 1 -C 6 alkylaminosulfonyl;
m选自0、1、2、3、4或5；m is selected from 0, 1, 2, 3, 4 or 5;
X 2和X 3可相同或不同的分别选自H、卤素、硝基、氰基、C 1-C 6烷基、C 1-C 6卤代烷基、C 2-C 6烯基、C 2-C 6卤代烯基、C 2-C 6炔基、C 2-C 6卤代炔基； X 2 and X 3 can be the same or different and are selected from H, halogen, nitro, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 - C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl;
R 1选自H、C 1-C 6烷基、C 1-C 6卤代烷基或氰基亚甲基； R 1 is selected from H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or cyano methylene;
R 2选自H、卤素、C 1-C 6烷基、C 1-C 6卤代烷基、C 2-C 6烯基、C 2-C 6卤代烯基、C 1-C 6烷基胺基、C 1-C 6卤代烷基胺基、C 1-C 6二烷基胺基、C 1-C 6卤代二烷基胺基、C 1-C 6烷氧基、C 1-C 6卤代烷氧基、C 2-C 6烯基氧基、C 2-C 6卤代烯基氧基、C 2-C 6炔基氧基、C 2-C 6卤代炔基氧基、C 1-C 6烷硫基、C 1-C 6卤代烷硫基、C 2-C 6烯基硫基、C 2-C 6卤代烯基硫基、C 2-C 6炔基硫基、C 2-C 6卤代炔基硫基、C 1-C 6烷氧基亚甲基、C 1-C 6卤代烷氧基亚甲基、C 1-C 6烷硫基亚甲基、C 1-C 6卤代烷硫基亚甲基、C 1-C 6烷胺基亚甲基、C 1-C 6卤代烷胺基亚甲基、C 1-C 6二烷胺基亚甲基、C 1-C 6卤代二烷胺基亚甲基、苯基、氨基、肼基、氰基、氰基亚甲基、1-吡咯烷基、1-哌啶基、4-吗啉基、1-1H-吡唑基、1-1H-咪唑基、1-1H-1,2,4-三氮唑基或2-2H-1,2,3-三氮唑基或4位被下述基团取代的哌嗪-1-基，其中下述基团为：C 1-C 6烷基、C 1-C 6烷基羰基或苯基； R 2 is selected from H, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkylamine C 1 -C 6 haloalkylamino group, C 1 -C 6 dialkylamino group, C 1 -C 6 halodialkylamino group, C 1 -C 6 alkoxy group , C 1 -C 6 Haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 2 -C 6 haloalkynyloxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 2 -C 6 alkenylthio, C 2 -C 6 haloalkenylthio, C 2 -C 6 alkynylthio, C 2 -C 6 haloalkynylthio, C 1 -C 6 alkoxymethylene, C 1 -C 6 haloalkoxymethylene, C 1 -C 6 alkylthiomethylene, C 1 -C 6 haloalkylthiomethylene, C 1 -C 6 alkylaminomethylene, C 1 -C 6 haloalkylaminomethylene, C 1 -C 6 dialkylaminomethylene, C 1 -C 6 Halodialkylaminomethylene, phenyl, amino, hydrazino, cyano, cyanomethylene, 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, 1-1H-pyridine Azolyl, 1-1H-imidazolyl, 1-1H-1,2,4-triazolyl or 2-2H-1,2,3-triazolyl or piperine substituted at the 4-position by the following groups Oxyzin-1-yl, wherein the following groups are: C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl or phenyl;
Y 1和Y 2可相同或不同的选自卤素、C 1-C 6烷基、C 1-C 6卤代烷基、C 1-C 6烷氧基、C 1-C 6卤代烷氧基、C 1-C 6烷硫基或C 1-C 6卤代烷硫基。 Y 1 and Y 2 may be the same or different and are selected from halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio or C 1 -C 6 haloalkylthio.
优选，所述通式I中：Preferably, in the general formula I:
Q选自
Figure PCTCN2022118920-appb-000003
Q from
Figure PCTCN2022118920-appb-000003
X 1选自卤素、硝基、氰基、CONH 2、CHO、C 1-C 3烷基、C 1-C 3卤代烷基、C 2-C 4烯基、C 2-C 4卤代烯基、C 2-C 4炔基、C 2-C 4卤代炔基、C 1-C 3烷氧基、C 1-C 3卤代烷氧基、C 1-C 3烷硫基、C 1-C 3卤代烷硫基、C 1-C 3烷基氨基、C 1-C 3二烷基氨基、C 1-C 3烷氧基羰基、C 1-C 3烷基羰基、C 1-C 3卤代烷基羰基、C 1-C 3烷基磺酰基、C 1-C 3卤代烷基磺酰基、C 1-C 3烷基亚磺酰基、C 1-C 3卤代烷基亚磺酰基、C 1-C 3烷基氨基羰基或C 1-C 3烷基氨基磺酰基； X 1 is selected from halogen, nitro, cyano, CONH 2 , CHO, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl , C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, C 1 -C 3 alkylamino, C 1 -C 3 dialkylamino, C 1 -C 3 alkoxycarbonyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkyl Carbonyl, C 1 -C 3 Alkylsulfonyl, C 1 -C 3 Haloalkylsulfonyl, C 1 -C 3 Alkylsulfinyl, C 1 -C 3 Haloalkylsulfinyl, C 1 -C 3 Alkane Aminocarbonyl or C 1 -C 3 alkylaminosulfonyl;
m选自0、1、2、3、4或5；m is selected from 0, 1, 2, 3, 4 or 5;
X 2和X 3可相同或不同的分别选自H、卤素、硝基、氰基、C 1-C 3烷基、C 1-C 3卤代烷基、C 2-C 4烯基、C 2-C 4卤代烯基、C 2-C 4炔基或C 2-C 4卤代炔基； X 2 and X 3 may be the same or different and are selected from H, halogen, nitro, cyano, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 4 alkenyl, C 2 - C 4 haloalkenyl, C 2 -C 4 alkynyl or C 2 -C 4 haloalkynyl;
R 1选自H、C 1-C 3烷基、C 1-C 3卤代烷基或氰基亚甲基； R 1 is selected from H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or cyano methylene;
R 2选自H、卤素、C 1-C 3烷基、C 1-C 3卤代烷基、C 2-C 4烯基、卤代C 2-C 4烯基、C 1-C 3烷基胺基、C 1-C 3卤代烷基胺基、C 1-C 3二烷基胺基、C 1-C 3卤代二烷基胺基、C 1-C 3烷氧基、C 1-C 3卤代烷基氧基、C 2-C 4烯基氧基、C 2-C 4卤代烯基氧基、C 2-C 4炔基氧基、C 2-C 4卤代炔基氧基、C 1-C 3烷硫基、C 1-C 3卤代烷基硫基、C 2-C 4烯基硫基、C 2-C 4卤代烯基硫基、C 2-C 4炔基硫基、C 2-C 4卤代炔基硫基、C 1-C 3烷氧基亚甲基、C 1-C 3卤代烷氧基亚甲基、C 1-C 3烷硫基亚甲基、C 1-C 3卤代烷硫基亚甲基、C 1-C 3烷胺基亚甲基、C 1-C 3卤代烷胺基亚甲基、C 1-C 3二烷胺基亚甲基、C 1-C 3卤代二烷胺基亚甲基、苯基、氨基、肼基、氰基、氰基亚甲基、1-吡咯烷基、1-哌啶基、4-吗啉基、1-1H-吡唑基、1-1H-咪唑基、1-1H-1,2,4-三氮唑基或2-2H-1,2,3-三氮唑基或4位被下述基团取代的哌嗪-1-基，其中下述基团为：C 1-C 3烷基、C 1-C 3烷基羰基或苯基； R 2 is selected from H, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 4 alkenyl, halogenated C 2 -C 4 alkenyl, C 1 -C 3 alkylamine C 1 -C 3 haloalkylamino, C 1 -C 3 dialkylamino, C 1 -C 3 halodialkylamino, C 1 -C 3 alkoxy , C 1 -C 3 Haloalkyloxy, C 2 -C 4 alkenyloxy, C 2 -C 4 haloalkenyloxy, C 2 -C 4 alkynyloxy, C 2 -C 4 haloalkynyloxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, C 2 -C 4 alkenylthio, C 2 -C 4 haloalkenylthio, C 2 -C 4 alkynylthio, C 2 -C 4 haloalkynylthio, C 1 -C 3 alkoxymethylene, C 1 -C 3 haloalkoxymethylene, C 1 -C 3 alkylthiomethylene, C 1 -C 3 haloalkylthiomethylene, C 1 -C 3 alkylaminomethylene, C 1 -C 3 haloalkylaminomethylene, C 1 -C 3 dialkylaminomethylene, C 1 - C 3 halodialkylaminomethylene, phenyl, amino, hydrazino, cyano, cyanomethylene, 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, 1-1H -pyrazolyl, 1-1H-imidazolyl, 1-1H-1,2,4-triazolyl or 2-2H-1,2,3-triazolyl or the 4th position is substituted by the following groups Piperazin-1-yl, wherein the following groups are: C 1 -C 3 alkyl, C 1 -C 3 alkylcarbonyl or phenyl;
Y 1和Y 2可相同或不同的选自卤素、C 1-C 3烷基、C 1-C 3卤代烷基、C 1-C 3烷氧基、C 1-C 3卤代烷氧基、C 1-C 3烷硫基或C 1-C 3卤代烷硫基。 Y 1 and Y 2 may be the same or different and are selected from halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio or C 1 -C 3 haloalkylthio.
进一步优选，所述通式I中：Further preferably, in the general formula I:
Q选自
Figure PCTCN2022118920-appb-000004
Q from
Figure PCTCN2022118920-appb-000004
X 1选自卤素、硝基、氰基、C 1-C 3卤代烷基、C 1-C 3烷氧基、C 1-C 3卤代烷氧基或C 1-C 3卤代烷硫基； X 1 is selected from halogen, nitro, cyano, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy or C 1 -C 3 haloalkylthio;
m选自0、1、2或3；m is selected from 0, 1, 2 or 3;
X 2和X 3可相同或不同的分别选自H或卤素； X 2 and X 3 can be the same or different and are independently selected from H or halogen;
R 1选自H或C 1-C 3烷基； R 1 is selected from H or C 1 -C 3 alkyl;
R 2选自卤素、C 1-C 3烷基胺基、C 1-C 3烷氧基、C 1-C 3烷硫基、1-1H-1,2,4-三氮唑基或4位被下述基团取代的哌嗪-1-基，其中下述基团为：C 1-C 3烷基、C 1-C 3烷基羰基或苯基； R 2 is selected from halogen, C 1 -C 3 alkylamino, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, 1-1H-1,2,4-triazolyl or 4 Piperazin-1-yl substituted by the following groups, wherein the following groups are: C 1 -C 3 alkyl, C 1 -C 3 alkylcarbonyl or phenyl;
Y 1和Y 2可相同或不同的选自卤素、C 1-C 3卤代烷基或C 1-C 3卤代烷氧基。 Y 1 and Y 2 may be the same or different and are selected from halogen, C 1 -C 3 haloalkyl or C 1 -C 3 haloalkoxy.
再进一步优选，所述通式I中：Still further preferably, in the general formula I:
Q选自
Figure PCTCN2022118920-appb-000005
Q from
Figure PCTCN2022118920-appb-000005
X 1选自F、Cl、Br、I、硝基、氰基、三氟甲基、甲氧基、二氟甲氧基、三氟甲氧基或三氟甲硫基； X is selected from F, Cl, Br, I, nitro, cyano, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy or trifluoromethylthio;
m选自0、1或2；m is selected from 0, 1 or 2;
X 2和X 3均选自F； Both X2 and X3 are selected from F;
R 1选自H或甲基； R is selected from H or methyl;
R 2选自F、Cl、Br、I、甲胺基、乙胺基、丙胺基、环丙烷基胺基、甲氧基、乙氧基、丙氧基、甲硫基、乙硫基、丙硫基、1-1H-1,2,4-三氮唑基或4-甲基哌嗪-1-基、4-乙基哌嗪-1-基、4-乙酰基哌嗪-1-基、4-苯基哌嗪-1-基； R is selected from F, Cl, Br, I, methylamino, ethylamino, propylamino, cyclopropanylamino, methoxy, ethoxy, propoxy, methylthio, ethylthio, propyl Thio, 1-1H-1,2,4-triazolyl or 4-methylpiperazin-1-yl, 4-ethylpiperazin-1-yl, 4-acetylpiperazin-1-yl , 4-phenylpiperazin-1-yl;
Y 1和Y 2可相同或不同的选自F、Cl、Br、I、三氟甲基、三氟甲氧基或二氟甲氧基。 Y1 and Y2 may be the same or different and are selected from F, Cl, Br, I, trifluoromethyl, trifluoromethoxy or difluoromethoxy.
更进一步优选，所述通式I中：More preferably, in the general formula I:
Q选自
Figure PCTCN2022118920-appb-000006
Q from
Figure PCTCN2022118920-appb-000006
X 1选自F、Cl、硝基、氰基、三氟甲基、甲氧基、二氟甲氧基、三氟甲氧基或三氟甲硫基； X is selected from F, Cl, nitro, cyano, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy or trifluoromethylthio;
m选自0、1或2；m is selected from 0, 1 or 2;
X 2和X 3均选自F； Both X2 and X3 are selected from F;
R 1选自甲基； R 1 is selected from methyl;
R 2选自Cl、Br、甲胺基、乙氧基、甲硫基、乙硫基、1-1H-1,2,4-三氮唑基或4-乙基哌嗪-1-基； R is selected from Cl, Br, methylamino, ethoxy, methylthio, ethylthio, 1-1H-1,2,4-triazolyl or 4-ethylpiperazin-1-yl;
Y 1和Y 2可相同或不同的选自Br、三氟甲基或二氟甲氧基。 Y 1 and Y 2 may be the same or different and are selected from Br, trifluoromethyl or difluoromethoxy.
本发明的通式I化合物可按照以下方法制备，除另有注明外，式中各基团的定义同前。The compound of general formula I of the present invention can be prepared according to the following methods, unless otherwise noted, the definition of each group in the formula is the same as before.
方法一(R 2为H、C 1-C 6烷基、C 1-C 6卤代烷基、C 2-C 6烯基、C 2-C 6卤代烯基、C 1-C 6烷氧基亚甲基、C 1-C 6卤代烷氧基亚甲基、C 1-C 6烷硫基亚甲基、C 1-C 6卤代烷硫基亚甲基、C 1-C 6烷胺基亚甲基、C 1-C 6卤代烷胺基亚甲基、C 1-C 6二烷胺基亚甲基、C 1-C 6卤代二烷胺基亚甲基、苯基或氰基亚甲基) Method 1 (R 2 is H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxy Methylene, C 1 -C 6 haloalkoxymethylene, C 1 -C 6 alkylthiomethylene, C 1 -C 6 haloalkylthiomethylene, C 1 -C 6 alkylaminomethylene C 1 -C 6 haloalkylaminomethylene, C 1 -C 6 dialkylaminomethylene, C 1 -C 6 halodialkylaminomethylene, phenyl or cyanomethylene )
Figure PCTCN2022118920-appb-000007
Figure PCTCN2022118920-appb-000007
具体合成方法如下，通式IV化合物与酰氯化试剂(如草酰氯和氯化亚砜等)反应制备酰氯III，酰氯III与通式V-a化合物反应制备通式II化合物，通式II化合物与取代苯胺V脱水反应制备亚胺，即通式I化合物。The specific synthesis method is as follows, the compound of general formula IV reacts with an acid chloride reagent (such as oxalyl chloride and thionyl chloride, etc.) to prepare acid chloride III, the compound of acid chloride III reacts with the compound of general formula V-a to prepare the compound of general formula II, and the compound of general formula II and substituted aniline The dehydration reaction of V prepares imines, that is, compounds of general formula I.
方法二(R 2为卤素) Method 2 (R 2 is halogen)
Figure PCTCN2022118920-appb-000008
Figure PCTCN2022118920-appb-000008
具体合成方法如下，通式VIII化合物与酰氯化试剂(如草酰氯和氯化亚砜等)反应制备酰氯VII，酰氯VII与取代苯胺V反应制备通式VI化合物，通式VI化合物与卤化试剂(如三氯氧磷和三溴氧磷等)脱水反应制备亚胺，即通式I化合物。The specific synthesis method is as follows, the compound of general formula VIII reacts with an acid chloride reagent (such as oxalyl chloride and thionyl chloride, etc.) to prepare acid chloride VII, the reaction of acid chloride VII and substituted aniline V prepares a compound of general formula VI, and the compound of general formula VI reacts with a halogenating reagent ( Such as phosphorus oxychloride and phosphorus oxybromide, etc.) dehydration reaction to prepare imines, that is, compounds of general formula I.
方法三(R 2为卤素) Method 3 (R 2 is halogen)
Figure PCTCN2022118920-appb-000009
Figure PCTCN2022118920-appb-000009
具体合成方法如下，2-氟-3-硝基苯甲酸与酰氯化试剂(如草酰氯和氯化亚砜等)反应制备2-氟-3-硝基苯甲酰氯，2-氟-3-硝基苯甲酰氯与取代苯胺V反应制备通式XI化合物，通式XI化合物硝基还原反应制备通式X化合物，通式X化合物烷基化反应制备通式IX化合物，通式IX化合物与酰氯III反应制备通式VI化合物，通式VI化合物与卤化试剂(如三氯氧磷和三溴氧磷等)脱水反应制备亚胺，即通式I化合物。The specific synthesis method is as follows, 2-fluoro-3-nitrobenzoic acid reacts with acyl chloride reagents (such as oxalyl chloride and thionyl chloride, etc.) to prepare 2-fluoro-3-nitrobenzoyl chloride, 2-fluoro-3- The reaction of nitrobenzoyl chloride and substituted aniline V to prepare the compound of general formula XI, the reduction reaction of the nitro group of the compound of general formula XI to prepare the compound of general formula X, the alkylation reaction of the compound of general formula X to prepare the compound of general formula IX, the compound of general formula IX and acid chloride III reaction to prepare the compound of general formula VI, the dehydration reaction of the compound of general formula VI with a halogenation reagent (such as phosphorus oxychloride and phosphorus oxybromide, etc.) to prepare imine, that is, the compound of general formula I.
方法四(R 2为C 1-C 6烷基胺基、C 1-C 6卤代烷基胺基、C 1-C 6二烷基胺基、C 1-C 6卤代二烷基胺基、C 1-C 6烷氧基、C 1-C 6卤代烷氧基、C 2-C 6烯基氧基、C 2-C 6卤代烯基氧基、C 2-C 6炔基氧基、C 2-C 6卤代炔基氧基、C 1-C 6烷硫基、C 1-C 6卤代烷硫基、C 2-C 6烯基硫基、C 2-C 6卤代烯基硫基、C 2-C 6炔基硫基、C 2-C 6卤代炔基硫基、氨基、肼基、氰基、1-吡咯烷基、1-哌啶基、4-取代哌嗪-1-基、4-吗啉基、1-1H-吡唑基、1-1H-咪唑基、1-1H-1,2,4-三氮唑基或2-2H-1,2,3-三氮唑基) Method 4 (R 2 is C 1 -C 6 alkylamino group, C 1 -C 6 haloalkylamino group, C 1 -C 6 dialkylamino group, C 1 -C 6 halodialkylamino group, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 2 -C 6 haloalkynyloxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 2 -C 6 alkenylthio, C 2 -C 6 haloalkenylthio Base, C 2 -C 6 alkynylthio, C 2 -C 6 haloalkynylthio, amino, hydrazino, cyano, 1-pyrrolidinyl, 1-piperidinyl, 4-substituted piperazine- 1-yl, 4-morpholinyl, 1-1H-pyrazolyl, 1-1H-imidazolyl, 1-1H-1,2,4-triazolyl or 2-2H-1,2,3- Triazolyl)
Figure PCTCN2022118920-appb-000010
Figure PCTCN2022118920-appb-000010
具体合成方法如下，通式VI化合物与三溴氧磷反应制备通式I-a化合物，通式I-a化合物进一步取代反应制备通式I化合物。The specific synthesis method is as follows, the compound of general formula VI is reacted with phosphorus oxybromide to prepare the compound of general formula I-a, and the compound of general formula I-a is further substituted to prepare the compound of general formula I.
上述制备方法中所涉及的原料及中间体来源如下：The raw materials and intermediate sources involved in the above-mentioned preparation method are as follows:
中间体V、中间体V-1和中间体X可以按US8853440B2方法制备。Intermediate V, intermediate V-1 and intermediate X can be prepared according to the method of US8853440B2.
酰卤化试剂、其它常规原料和试剂通常有市售，也可按照常规方法自制。Acid halide reagents, other conventional raw materials and reagents are usually commercially available, and can also be self-made according to conventional methods.
上面给出的通式化合物的定义中，汇集所用术语一般代表如下取代基：In the definitions given above for compounds of the general formula, the collective terms used generally represent the following substituents:
卤素：指氟、氯、溴或碘。Halogen: refers to fluorine, chlorine, bromine or iodine.
烷基：直链、支链或环状烷基，例如甲基、乙基、正丙基、异丙基或环丙基等。Alkyl: linear, branched or cyclic alkyl, such as methyl, ethyl, n-propyl, isopropyl or cyclopropyl, etc.
卤代烷基：直链、支链或环状烷基，在这些烷基上的氢原子可部分或全部被卤素所取代，例如氯甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、五氟乙基或七氟异丙基 等。Haloalkyl: Straight chain, branched or cyclic alkyl, the hydrogen atoms on these alkyl groups can be partially or completely replaced by halogen, such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, Difluoromethyl, trifluoromethyl, pentafluoroethyl or heptafluoroisopropyl, etc.
烯基：直链、支链或环状烯基，例如乙烯基、1-丙烯基、2-丙烯基和不同的丁烯基、戊烯基和己烯基异构体；烯基还包括多烯类如1,2-丙二烯基和2,4-己二烯基等。Alkenyl: straight-chain, branched or cyclic alkenyl groups such as vinyl, 1-propenyl, 2-propenyl and the different butenyl, pentenyl and hexenyl isomers; alkenyl also includes polyenes Classes such as 1,2-propadienyl and 2,4-hexadienyl, etc.
卤代烯基：可被卤原子取代至少一个或多个氢原子的烯基。Haloalkenyl: an alkenyl group in which at least one or more hydrogen atoms may be replaced by a halogen atom.
炔基：包括直链或支链炔基，如乙炔基、1-丙炔基和不同的丁炔基、戊炔基和己炔基异构体；炔基还包括由多个三键组成的基团，例如2,5-己二炔基。Alkynyl: includes straight or branched chain alkynyl groups such as ethynyl, 1-propynyl and the different butynyl, pentynyl and hexynyl isomers; alkynyl also includes radicals consisting of multiple triple bonds group, such as 2,5-hexadiynyl.
卤代炔基：可被卤原子取代至少一个或多个氢原子的炔基。Haloalkynyl: an alkynyl group in which at least one or more hydrogen atoms may be replaced by halogen atoms.
烷氧基：直链、支链或环状烷氧基，例如甲氧基、乙氧基、正丙氧基、异丙氧基、环丙基氧基或正丁氧基等。Alkoxy: linear, branched or cyclic alkoxy, such as methoxy, ethoxy, n-propoxy, isopropoxy, cyclopropyloxy or n-butoxy, etc.
卤代烷氧基：直链、支链或环状烷氧基，在这些烷氧基上的氢原子可部分或全部被卤素所取代，例如氯甲氧基、二氯甲氧基、三氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氯氟甲氧基、三氟乙氧基、七氟异丙基氧基等。Halogenated alkoxy: straight chain, branched or cyclic alkoxy, the hydrogen atoms on these alkoxy can be partially or completely replaced by halogen, such as chloromethoxy, dichloromethoxy, trichloromethoxy fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy, heptafluoroisopropyloxy, etc.
烷硫基：直链、支链或环状烷基，经硫原子键连接到结构上，例如甲硫基、乙硫基等。Alkylthio: Straight-chain, branched or cyclic alkyl, bonded to the structure via a sulfur atom, such as methylthio, ethylthio, etc.
卤代烷硫基：直链、支链或环状烷硫基，在这些烷硫基上的氢原子可部分或全部被卤素所取代，例如二氟甲硫基、三氟乙硫基等。Halogenated alkylthio: straight chain, branched or cyclic alkylthio, the hydrogen atoms on these alkylthio can be partially or completely replaced by halogen, such as difluoromethylthio, trifluoroethylthio, etc.
烯基硫基：直链、支链或环状烯基，经硫原子键连接到结构上，例如1-丙烯基-3-硫基、2-丁烯基-4-硫基等。Alkenylthio: straight-chain, branched-chain or cyclic alkenyl, bonded to the structure via a sulfur atom, such as 1-propenyl-3-thio, 2-butenyl-4-thio, etc.
卤代烯基硫基：直链、支链或环状烯基硫基，在这些烯基硫基上的氢原子可部分或全部被卤素所取代。Haloalkenylthio: straight-chain, branched or cyclic alkenylthio, the hydrogen atoms on these alkenylthio can be partially or fully replaced by halogen.
炔基硫基：直链、支链或环状炔基，经硫原子键连接到结构上，例如1-丙炔基-3-硫基、2-丁炔基-4-硫基等。Alkynylthio: straight-chain, branched-chain or cyclic alkynyl, bonded to the structure via a sulfur atom, such as 1-propynyl-3-thio, 2-butynyl-4-thio, etc.
卤代炔基硫基：直链、支链或环状炔基硫基，在这些炔基硫基上的氢原子可部分或全部被卤素所取代。Haloalkynylthio: Straight-chain, branched or cyclic alkynylthio. The hydrogen atoms on these alkynylthio groups can be partially or completely replaced by halogen.
烷基氨基：直链、支链或环状烷基，经氮原子键连接到结构上，例如甲基氨基、乙基氨基、正丙基氨基、异丙基氨基或同分异构的丁基胺基。Alkylamino: Straight-chain, branched-chain, or cyclic alkyl group bonded to the structure via a nitrogen atom bond, such as methylamino, ethylamino, n-propylamino, isopropylamino, or isomeric butyl Amino.
二烷基氨基：两个相同或不同的直链、支链或环状烷基，经氮原子键连接到结构上，例如二甲基氨基、甲基乙基氨基、二环丙基氨基等。Dialkylamino: Two identical or different straight-chain, branched-chain or cyclic alkyl groups linked to the structure via a nitrogen atom bond, such as dimethylamino, methylethylamino, dicyclopropylamino, etc.
烷氧基羰基：烷基-O-CO-，例如CH 3OCO-。 Alkoxycarbonyl: alkyl-O-CO-, eg CH 3 OCO-.
烷基羰基：烷基-CO-，例如CH 3CO- Alkylcarbonyl: alkyl-CO-, such as CH3CO-
烷基磺酰基：烷基-S(O) 2-，例如甲基磺酰基。 Alkylsulfonyl: alkyl-S(O) 2 -, such as methylsulfonyl.
烷基亚磺酰基：烷基-S(O)-，例如甲基亚磺酰基。Alkylsulfinyl: alkyl-S(O)-, eg methylsulfinyl.
烷基氨基羰基：烷基-NH-CO-，例如CH 3NHCO-。 Alkylaminocarbonyl: alkyl-NH-CO-, eg CH 3 NHCO-.
烷基氨基磺酰基：烷基-NH-S(O) 2-，例如CH 3NH S(O) 2-。 Alkylaminosulfonyl: alkyl-NH-S(O) 2 -, eg CH 3 NHS(O) 2 -.
在本发明的化合物中，由于X 2和X 3的不同，通式I化合物是手性(chirality)结构化合物，此时，化合物可以以单一手性异构体或两种手性异构体混合形式存在；通式I化合物亚胺结构的存在几何异构，化合物可以以单一几何异构体或两种几何异构体混合形式存在，本发明所要保护的通式I所示化合物并不受上述异构体结构存在形式限定。 In the compound of the present invention, due to the difference between X 2 and X 3 , the compound of general formula I is a chirality structure compound. At this time, the compound can be mixed with a single chiral isomer or two chiral isomers Existing in different forms; the imine structure of the compound of general formula I has geometric isomerism, and the compound can exist in the form of a single geometric isomer or a mixture of two geometric isomers. The compound shown in the general formula I to be protected by the present invention is not protected by the above Isomer structures exist as formal limitations.
表1中列出的具体化合物可以用来说明本发明，但并不限定本发明。The specific compounds listed in Table 1 serve to illustrate the invention, but do not limit it.
表1Table 1
Figure PCTCN2022118920-appb-000011
Figure PCTCN2022118920-appb-000011
II
编号serial number QQ R 1 R 1 R 2 R 2 Y 1 Y 1 Y 2 Y 2
I-1I-1 phenylphenyl CH 3 CH3 CH 3 CH3 II II
I-2I-2 phenylphenyl CH 3 CH3 CH 3 CH3 BrBr BrBr
I-3I-3 phenylphenyl CH 3 CH3 CH 3 CH3 ClCl ClCl
I-4I-4 phenylphenyl CH 3 CH3 CH 3 CH3 Ff Ff
I-5I-5 phenylphenyl CH 3 CH3 CH 3 CH3 BrBr CH 3 CH3
I-6I-6 phenylphenyl CH 3 CH3 CH 3 CH3 BrBr CF 3 CF 3
I-7I-7 phenylphenyl CH 3 CH3 CH 3 CH3 BrBr OCF 3 OCF 3
I-8I-8 phenylphenyl CH 3 CH3 CH 3 CH3 BrBr OCHF 2 OCHF 2
I-9I-9 phenylphenyl CH 3 CH3 Hh II II
I-10I-10 phenylphenyl CH 3 CH3 Hh BrBr BrBr
I-11I-11 phenylphenyl CH 3 CH3 Hh ClCl ClCl
I-12I-12 phenylphenyl CH 3 CH3 Hh Ff Ff
I-13I-13 phenylphenyl CH 3 CH3 Hh BrBr CH 3 CH3
I-14I-14 phenylphenyl CH 3 CH3 Hh BrBr CF 3 CF 3
I-15I-15 phenylphenyl CH 3 CH3 Hh BrBr OCF 3 OCF 3
I-16I-16 phenylphenyl CH 3 CH3 Hh BrBr OCHF 2 OCHF 2
I-17I-17 phenylphenyl Hh CH 3 CH3 II II
I-18I-18 phenylphenyl Hh CH 3 CH3 BrBr BrBr
I-19I-19 phenylphenyl Hh CH 3 CH3 ClCl ClCl
I-20I-20 phenylphenyl Hh CH 3 CH3 Ff Ff
I-21I-21 phenylphenyl Hh CH 3 CH3 BrBr CH 3 CH3
I-22I-22 phenylphenyl Hh CH 3 CH3 BrBr CF 3 CF 3
I-23I-23 phenylphenyl Hh CH 3 CH3 BrBr OCF 3 OCF 3
I-24I-24 phenylphenyl Hh CH 3 CH3 BrBr OCHF 2 OCHF 2
I-25I-25 phenylphenyl Hh Hh II II
I-26I-26 phenylphenyl Hh Hh BrBr BrBr
I-27I-27 phenylphenyl Hh Hh ClCl ClCl
I-28I-28 phenylphenyl Hh Hh Ff Ff
I-29I-29 phenylphenyl Hh Hh BrBr CH 3 CH3
I-30I-30 phenylphenyl Hh Hh BrBr CF 3 CF 3
I-31I-31 phenylphenyl Hh Hh BrBr OCF 3 OCF 3
I-32I-32 phenylphenyl Hh Hh BrBr OCHF 2 OCHF 2
I-33I-33 phenylphenyl CH 3 CH3 ClCl II II
I-34I-34 phenylphenyl CH 3 CH3 ClCl BrBr BrBr
I-35I-35 phenylphenyl CH 3 CH3 ClCl ClCl ClCl
I-36I-36 phenylphenyl CH 3 CH3 ClCl Ff Ff
I-37I-37 phenylphenyl CH 3 CH3 ClCl BrBr CH 3 CH3
I-38I-38 phenylphenyl CH 3 CH3 ClCl BrBr CF 3 CF 3
I-39I-39 phenylphenyl CH 3 CH3 ClCl BrBr OCF 3 OCF 3
I-40I-40 phenylphenyl CH 3 CH3 ClCl BrBr OCHF 2 OCHF 2
I-41I-41 phenylphenyl CH 3 CH3 BrBr II II
I-42I-42 phenylphenyl CH 3 CH3 BrBr BrBr BrBr
I-43I-43 phenylphenyl CH 3 CH3 BrBr ClCl ClCl
I-44I-44 phenylphenyl CH 3 CH3 BrBr Ff Ff
I-45I-45 phenylphenyl CH 3 CH3 BrBr BrBr CH 3 CH3
I-46I-46 phenylphenyl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-47I-47 phenylphenyl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-48I-48 phenylphenyl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
I-49I-49 phenylphenyl CH 3 CH3 SCH 3 SCH 3 II II
I-50I-50 phenylphenyl CH 3 CH3 SCH 3 SCH 3 BrBr BrBr
I-51I-51 phenylphenyl CH 3 CH3 SCH 3 SCH 3 ClCl ClCl
I-52I-52 phenylphenyl CH 3 CH3 SCH 3 SCH 3 Ff Ff
I-53I-53 phenylphenyl CH 3 CH3 SCH 3 SCH 3 BrBr CH 3 CH3
I-54I-54 phenylphenyl CH 3 CH3 SCH 3 SCH 3 BrBr CF 3 CF 3
I-55I-55 phenylphenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCF 3 OCF 3
I-56I-56 phenylphenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCHF 2 OCHF 2
I-57I-57 phenylphenyl cyclopropylmethylcyclopropylmethyl BrBr II II
I-58I-58 phenylphenyl cyclopropylmethylcyclopropylmethyl BrBr BrBr BrBr
I-59I-59 phenylphenyl cyclopropylmethylcyclopropylmethyl BrBr ClCl ClCl
I-60I-60 phenylphenyl cyclopropylmethylcyclopropylmethyl BrBr Ff Ff
I-61I-61 phenylphenyl cyclopropylmethylcyclopropylmethyl BrBr BrBr CH 3 CH3
I-62I-62 phenylphenyl cyclopropylmethylcyclopropylmethyl BrBr BrBr CF 3 CF 3
I-63I-63 phenylphenyl cyclopropylmethylcyclopropylmethyl BrBr BrBr OCF 3 OCF 3
I-64I-64 phenylphenyl cyclopropylmethylcyclopropylmethyl BrBr BrBr OCHF 2 OCHF 2
I-65I-65 phenylphenyl cyclopropylmethylcyclopropylmethyl ClCl II II
I-66I-66 phenylphenyl cyclopropylmethylcyclopropylmethyl ClCl BrBr BrBr
I-67I-67 phenylphenyl cyclopropylmethylcyclopropylmethyl ClCl ClCl ClCl
I-68I-68 phenylphenyl cyclopropylmethylcyclopropylmethyl ClCl Ff Ff
I-69I-69 phenylphenyl cyclopropylmethylcyclopropylmethyl ClCl BrBr CH 3 CH3
I-70I-70 phenylphenyl cyclopropylmethylcyclopropylmethyl ClCl BrBr CF 3 CF 3
I-71I-71 phenylphenyl cyclopropylmethylcyclopropylmethyl ClCl BrBr OCF 3 OCF 3
I-72I-72 phenylphenyl cyclopropylmethylcyclopropylmethyl ClCl BrBr OCHF 2 OCHF 2
I-73I-73 4-fluorophenyl4-fluorophenyl cyclopropylmethylcyclopropylmethyl BrBr II II
I-74I-74 4-fluorophenyl4-fluorophenyl cyclopropylmethylcyclopropylmethyl BrBr BrBr BrBr
I-75I-75 4-fluorophenyl4-fluorophenyl cyclopropylmethylcyclopropylmethyl BrBr ClCl ClCl
I-76I-76 4-fluorophenyl4-fluorophenyl cyclopropylmethylcyclopropylmethyl BrBr Ff Ff
I-77I-77 4-fluorophenyl4-fluorophenyl cyclopropylmethylcyclopropylmethyl BrBr BrBr CH 3 CH3
I-78I-78 4-fluorophenyl4-fluorophenyl cyclopropylmethylcyclopropylmethyl BrBr BrBr CF 3 CF 3
I-79I-79 4-fluorophenyl4-fluorophenyl cyclopropylmethylcyclopropylmethyl BrBr BrBr OCF 3 OCF 3
I-80I-80 4-fluorophenyl4-fluorophenyl cyclopropylmethylcyclopropylmethyl BrBr BrBr OCHF 2 OCHF 2
I-81I-81 4-fluorophenyl4-fluorophenyl cyclopropylmethylcyclopropylmethyl ClCl II II
I-82I-82 4-fluorophenyl4-fluorophenyl cyclopropylmethylcyclopropylmethyl ClCl BrBr BrBr
I-83I-83 4-fluorophenyl4-fluorophenyl cyclopropylmethylcyclopropylmethyl ClCl ClCl ClCl
I-84I-84 4-fluorophenyl4-fluorophenyl cyclopropylmethylcyclopropylmethyl ClCl Ff Ff
I-85I-85 4-fluorophenyl4-fluorophenyl cyclopropylmethylcyclopropylmethyl ClCl BrBr CH 3 CH3
I-86I-86 4-fluorophenyl4-fluorophenyl cyclopropylmethylcyclopropylmethyl ClCl BrBr CF 3 CF 3
I-87I-87 4-fluorophenyl4-fluorophenyl cyclopropylmethylcyclopropylmethyl ClCl BrBr OCF 3 OCF 3
I-88I-88 4-fluorophenyl4-fluorophenyl cyclopropylmethylcyclopropylmethyl ClCl BrBr OCHF 2 OCHF 2
I-89I-89 4-fluorophenyl4-fluorophenyl CH 3 CH3 BrBr II II
I-90I-90 4-fluorophenyl4-fluorophenyl CH 3 CH3 BrBr BrBr BrBr
I-91I-91 4-fluorophenyl4-fluorophenyl CH 3 CH3 BrBr ClCl ClCl
I-92I-92 4-fluorophenyl4-fluorophenyl CH 3 CH3 BrBr Ff Ff
I-93I-93 4-fluorophenyl4-fluorophenyl CH 3 CH3 BrBr BrBr CH 3 CH3
I-94I-94 4-fluorophenyl4-fluorophenyl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-95I-95 4-fluorophenyl4-fluorophenyl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-96I-96 4-fluorophenyl4-fluorophenyl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
I-97I-97 4-fluorophenyl4-fluorophenyl CH 3 CH3 ClCl II II
I-98I-98 4-fluorophenyl4-fluorophenyl CH 3 CH3 ClCl BrBr BrBr
I-99I-99 4-fluorophenyl4-fluorophenyl CH 3 CH3 ClCl ClCl ClCl
I-100I-100 4-fluorophenyl4-fluorophenyl CH 3 CH3 ClCl Ff Ff
I-101I-101 4-fluorophenyl4-fluorophenyl CH 3 CH3 ClCl BrBr CH 3 CH3
I-102I-102 4-fluorophenyl4-fluorophenyl CH 3 CH3 ClCl BrBr CF 3 CF 3
I-103I-103 4-fluorophenyl4-fluorophenyl CH 3 CH3 ClCl BrBr OCF 3 OCF 3
I-104I-104 4-fluorophenyl4-fluorophenyl CH 3 CH3 ClCl BrBr OCHF 2 OCHF 2
I-105I-105 benzo[d][1,3]dioxol-5-ylbenzo[d][1,3]dioxol-5-yl CH 3 CH3 BrBr II II
I-106I-106 benzo[d][1,3]dioxol-5-ylbenzo[d][1,3]dioxol-5-yl CH 3 CH3 BrBr BrBr BrBr
I-107I-107 benzo[d][1,3]dioxol-5-ylbenzo[d][1,3]dioxol-5-yl CH 3 CH3 BrBr ClCl ClCl
I-108I-108 benzo[d][1,3]dioxol-5-ylbenzo[d][1,3]dioxol-5-yl CH 3 CH3 BrBr Ff Ff
I-109I-109 benzo[d][1,3]dioxol-5-ylbenzo[d][1,3]dioxol-5-yl CH 3 CH3 BrBr BrBr CH 3 CH3
I-110I-110 benzo[d][1,3]dioxol-5-ylbenzo[d][1,3]dioxol-5-yl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-111I-111 benzo[d][1,3]dioxol-5-ylbenzo[d][1,3]dioxol-5-yl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-112I-112 benzo[d][1,3]dioxol-5-ylbenzo[d][1,3]dioxol-5-yl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
I-113I-113 benzo[d][1,3]dioxol-5-ylbenzo[d][1,3]dioxol-5-yl CH 3 CH3 ClCl II II
I-114I-114 benzo[d][1,3]dioxol-5-ylbenzo[d][1,3]dioxol-5-yl CH 3 CH3 ClCl BrBr BrBr
I-115I-115 benzo[d][1,3]dioxol-5-ylbenzo[d][1,3]dioxol-5-yl CH 3 CH3 ClCl ClCl ClCl
I-116I-116 benzo[d][1,3]dioxol-5-ylbenzo[d][1,3]dioxol-5-yl CH 3 CH3 ClCl Ff Ff
I-117I-117 benzo[d][1,3]dioxol-5-ylbenzo[d][1,3]dioxol-5-yl CH 3 CH3 ClCl BrBr CH 3 CH3
I-118I-118 benzo[d][1,3]dioxol-5-ylbenzo[d][1,3]dioxol-5-yl CH 3 CH3 ClCl BrBr CF 3 CF 3
I-119I-119 benzo[d][1,3]dioxol-5-ylbenzo[d][1,3]dioxol-5-yl CH 3 CH3 ClCl BrBr OCF 3 OCF 3
I-120I-120 benzo[d][1,3]dioxol-5-ylbenzo[d][1,3]dioxol-5-yl CH 3 CH3 ClCl BrBr OCHF 2 OCHF 2
I-121I-121 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 BrBr II II
I-122I-122 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 BrBr BrBr BrBr
I-123I-123 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 BrBr ClCl ClCl
I-124I-124 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 BrBr Ff Ff
I-125I-125 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 BrBr BrBr CH 3 CH3
I-126I-126 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-127I-127 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-128I-128 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
I-129I-129 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 ClCl II II
I-130I-130 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 ClCl BrBr BrBr
I-131I-131 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 ClCl ClCl ClCl
I-132I-132 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 ClCl Ff Ff
I-133I-133 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 ClCl BrBr CH 3 CH3
I-134I-134 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 ClCl BrBr CF 3 CF 3
I-135I-135 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 ClCl BrBr OCF 3 OCF 3
I-136I-136 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 ClCl BrBr OCHF 2 OCHF 2
I-137I-137 3-fluorophenyl3-fluorophenyl CH 3 CH3 BrBr II II
I-138I-138 3-fluorophenyl3-fluorophenyl CH 3 CH3 BrBr BrBr BrBr
I-139I-139 3-fluorophenyl3-fluorophenyl CH 3 CH3 BrBr ClCl ClCl
I-140I-140 3-fluorophenyl3-fluorophenyl CH 3 CH3 BrBr Ff Ff
I-141I-141 3-fluorophenyl3-fluorophenyl CH 3 CH3 BrBr BrBr CH 3 CH3
I-142I-142 3-fluorophenyl3-fluorophenyl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-143I-143 3-fluorophenyl3-fluorophenyl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-144I-144 3-fluorophenyl3-fluorophenyl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
I-145I-145 3-fluorophenyl3-fluorophenyl CH 3 CH3 ClCl II II
I-146I-146 3-fluorophenyl3-fluorophenyl CH 3 CH3 ClCl BrBr BrBr
I-147I-147 3-fluorophenyl3-fluorophenyl CH 3 CH3 ClCl ClCl ClCl
I-148I-148 3-fluorophenyl3-fluorophenyl CH 3 CH3 ClCl Ff Ff
I-149I-149 3-fluorophenyl3-fluorophenyl CH 3 CH3 ClCl BrBr CH 3 CH3
I-150I-150 3-fluorophenyl3-fluorophenyl CH 3 CH3 ClCl BrBr CF 3 CF 3
I-151I-151 3-fluorophenyl3-fluorophenyl CH 3 CH3 ClCl BrBr OCF 3 OCF 3
I-152I-152 3-fluorophenyl3-fluorophenyl CH 3 CH3 ClCl BrBr OCHF 2 OCHF 2
I-153I-153 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 BrBr II II
I-154I-154 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 BrBr BrBr BrBr
I-155I-155 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 BrBr ClCl ClCl
I-156I-156 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 BrBr Ff Ff
I-157I-157 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 BrBr BrBr CH 3 CH3
I-158I-158 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-159I-159 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-160I-160 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
I-161I-161 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 ClCl II II
I-162I-162 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 ClCl BrBr BrBr
I-163I-163 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 ClCl ClCl ClCl
I-164I-164 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 ClCl Ff Ff
I-165I-165 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 ClCl BrBr CH 3 CH3
I-166I-166 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 ClCl BrBr CF 3 CF 3
I-167I-167 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 ClCl BrBr OCF 3 OCF 3
I-168I-168 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 ClCl BrBr OCHF 2 OCHF 2
I-169I-169 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 SCH 3 SCH 3 II II
I-170I-170 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 SCH 3 SCH 3 BrBr BrBr
I-171I-171 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 SCH 3 SCH 3 ClCl ClCl
I-172I-172 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 SCH 3 SCH 3 Ff Ff
I-173I-173 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 SCH 3 SCH 3 BrBr CH 3 CH3
I-174I-174 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 SCH 3 SCH 3 BrBr CF 3 CF 3
I-175I-175 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 SCH 3 SCH 3 BrBr OCF 3 OCF 3
I-176I-176 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 SCH 3 SCH 3 BrBr OCHF 2 OCHF 2
I-177I-177 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 CH 3 CH3 II II
I-178I-178 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 CH 3 CH3 BrBr BrBr
I-179I-179 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 CH 3 CH3 ClCl ClCl
I-180I-180 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 CH 3 CH3 Ff Ff
I-181I-181 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 CH 3 CH3 BrBr CH 3 CH3
I-182I-182 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 CH 3 CH3 BrBr CF 3 CF 3
I-183I-183 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 CH 3 CH3 BrBr OCF 3 OCF 3
I-184I-184 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 CH 3 CH3 BrBr OCHF 2 OCHF 2
I-185I-185 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 Hh II II
I-186I-186 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 Hh BrBr BrBr
I-187I-187 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 Hh ClCl ClCl
I-188I-188 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 Hh Ff Ff
I-189I-189 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 Hh BrBr CH 3 CH3
I-190I-190 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 Hh BrBr CF 3 CF 3
I-191I-191 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 Hh BrBr OCF 3 OCF 3
I-192I-192 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 Hh BrBr OCHF 2 OCHF 2
I-193I-193 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 ClCl II II
I-194I-194 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 ClCl BrBr BrBr
I-195I-195 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 ClCl ClCl ClCl
I-196I-196 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 ClCl Ff Ff
I-197I-197 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 ClCl BrBr CH 3 CH3
I-198I-198 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 ClCl BrBr CF 3 CF 3
I-199I-199 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 ClCl BrBr OCF 3 OCF 3
I-200I-200 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 ClCl BrBr OCHF 2 OCHF 2
I-201I-201 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 BrBr II II
I-202I-202 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 BrBr BrBr BrBr
I-203I-203 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 BrBr ClCl ClCl
I-204I-204 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 BrBr Ff Ff
I-205I-205 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 BrBr BrBr CH 3 CH3
I-206I-206 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-207I-207 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-208I-208 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
I-209I-209 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 SCH 3 SCH 3 II II
I-210I-210 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr BrBr
I-211I-211 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 SCH 3 SCH 3 ClCl ClCl
I-212I-212 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 SCH 3 SCH 3 Ff Ff
I-213I-213 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CH 3 CH3
I-214I-214 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CF 3 CF 3
I-215I-215 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCF 3 OCF 3
I-216I-216 2,4-difluorophenyl2,4-difluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCHF 2 OCHF 2
I-217I-217 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 ClCl II II
I-218I-218 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 ClCl BrBr BrBr
I-219I-219 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 ClCl ClCl ClCl
I-220I-220 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 ClCl Ff Ff
I-221I-221 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 ClCl BrBr CH 3 CH3
I-222I-222 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 ClCl BrBr CF 3 CF 3
I-223I-223 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 ClCl BrBr OCF 3 OCF 3
I-224I-224 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 ClCl BrBr OCHF 2 OCHF 2
I-225I-225 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 BrBr II II
I-226I-226 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 BrBr BrBr BrBr
I-227I-227 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 BrBr ClCl ClCl
I-228I-228 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 BrBr Ff Ff
I-229I-229 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 BrBr BrBr CH 3 CH3
I-230I-230 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-231I-231 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-232I-232 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
I-233I-233 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 SCH 3 SCH 3 II II
I-234I-234 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr BrBr
I-235I-235 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 SCH 3 SCH 3 ClCl ClCl
I-236I-236 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 SCH 3 SCH 3 Ff Ff
I-237I-237 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CH 3 CH3
I-238I-238 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CF 3 CF 3
I-239I-239 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCF 3 OCF 3
I-240I-240 3,5-dichlorophenyl3,5-dichlorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCHF 2 OCHF 2
I-241I-241 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 ClCl II II
I-242I-242 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 ClCl BrBr BrBr
I-243I-243 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 ClCl ClCl ClCl
I-244I-244 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 ClCl Ff Ff
I-245I-245 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 ClCl BrBr CH 3 CH3
I-246I-246 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 ClCl BrBr CF 3 CF 3
I-247I-247 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 ClCl BrBr OCF 3 OCF 3
I-248I-248 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 ClCl BrBr OCHF 2 OCHF 2
I-249I-249 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 BrBr II II
I-250I-250 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 BrBr BrBr BrBr
I-251I-251 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 BrBr ClCl ClCl
I-252I-252 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 BrBr Ff Ff
I-253I-253 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 BrBr BrBr CH 3 CH3
I-254I-254 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-255I-255 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-256I-256 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
I-257I-257 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 SCH 3 SCH 3 II II
I-258I-258 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr BrBr
I-259I-259 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 SCH 3 SCH 3 ClCl ClCl
I-260I-260 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 SCH 3 SCH 3 Ff Ff
I-261I-261 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CH 3 CH3
I-262I-262 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CF 3 CF 3
I-263I-263 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCF 3 OCF 3
I-264I-264 3,4-dichlorophenyl3,4-dichlorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCHF 2 OCHF 2
I-265I-265 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 ClCl II II
I-266I-266 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 ClCl BrBr BrBr
I-267I-267 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 ClCl ClCl ClCl
I-268I-268 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 ClCl Ff Ff
I-269I-269 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 ClCl BrBr CH 3 CH3
I-270I-270 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 ClCl BrBr CF 3 CF 3
I-271I-271 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 ClCl BrBr OCF 3 OCF 3
I-272I-272 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 ClCl BrBr OCHF 2 OCHF 2
I-273I-273 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 BrBr II II
I-274I-274 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 BrBr BrBr BrBr
I-275I-275 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 BrBr ClCl ClCl
I-276I-276 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 BrBr Ff Ff
I-277I-277 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 BrBr BrBr CH 3 CH3
I-278I-278 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-279I-279 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-280I-280 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
I-281I-281 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 II II
I-282I-282 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr BrBr
I-283I-283 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 ClCl ClCl
I-284I-284 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 Ff Ff
I-285I-285 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr CH 3 CH3
I-286I-286 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr CF 3 CF 3
I-287I-287 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCF 3 OCF 3
I-288I-288 4-trifluoromethoxyphenyl4-trifluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCHF 2 OCHF 2
I-289I-289 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 ClCl II II
I-290I-290 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 ClCl BrBr BrBr
I-291I-291 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 ClCl ClCl ClCl
I-292I-292 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 ClCl Ff Ff
I-293I-293 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 ClCl BrBr CH 3 CH3
I-294I-294 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 ClCl BrBr CF 3 CF 3
I-295I-295 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 ClCl BrBr OCF 3 OCF 3
I-296I-296 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 ClCl BrBr OCHF 2 OCHF 2
I-297I-297 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 BrBr II II
I-298I-298 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 BrBr BrBr BrBr
I-299I-299 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 BrBr ClCl ClCl
I-300I-300 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 BrBr Ff Ff
I-301I-301 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 BrBr BrBr CH 3 CH3
I-302I-302 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-303I-303 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-304I-304 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
I-305I-305 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 SCH 3 SCH 3 II II
I-306I-306 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 SCH 3 SCH 3 BrBr BrBr
I-307I-307 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 SCH 3 SCH 3 ClCl ClCl
I-308I-308 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 SCH 3 SCH 3 Ff Ff
I-309I-309 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CH 3 CH3
I-310I-310 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CF 3 CF 3
I-311I-311 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCF 3 OCF 3
I-312I-312 4-trifluoromethylthiophenyl4-trifluoromethylthiophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCHF 2 OCHF 2
I-313I-313 4-nitrophenyl4-nitrophenyl CH 3 CH3 ClCl II II
I-314I-314 4-nitrophenyl4-nitrophenyl CH 3 CH3 ClCl BrBr BrBr
I-315I-315 4-nitrophenyl4-nitrophenyl CH 3 CH3 ClCl ClCl ClCl
I-316I-316 4-nitrophenyl4-nitrophenyl CH 3 CH3 ClCl Ff Ff
I-317I-317 4-nitrophenyl4-nitrophenyl CH 3 CH3 ClCl BrBr CH 3 CH3
I-318I-318 4-nitrophenyl4-nitrophenyl CH 3 CH3 ClCl BrBr CF 3 CF 3
I-319I-319 4-nitrophenyl4-nitrophenyl CH 3 CH3 ClCl BrBr OCF 3 OCF 3
I-320I-320 4-nitrophenyl4-nitrophenyl CH 3 CH3 ClCl BrBr OCHF 2 OCHF 2
I-321I-321 4-nitrophenyl4-nitrophenyl CH 3 CH3 BrBr II II
I-322I-322 4-nitrophenyl4-nitrophenyl CH 3 CH3 BrBr BrBr BrBr
I-323I-323 4-nitrophenyl4-nitrophenyl CH 3 CH3 BrBr ClCl ClCl
I-324I-324 4-nitrophenyl4-nitrophenyl CH 3 CH3 BrBr Ff Ff
I-325I-325 4-nitrophenyl4-nitrophenyl CH 3 CH3 BrBr BrBr CH 3 CH3
I-326I-326 4-nitrophenyl4-nitrophenyl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-327I-327 4-nitrophenyl4-nitrophenyl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-328I-328 4-nitrophenyl4-nitrophenyl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
I-329I-329 4-nitrophenyl4-nitrophenyl CH 3 CH3 SCH 3 SCH 3 II II
I-330I-330 4-nitrophenyl4-nitrophenyl CH 3 CH3 SCH 3 SCH 3 BrBr BrBr
I-331I-331 4-nitrophenyl4-nitrophenyl CH 3 CH3 SCH 3 SCH 3 ClCl ClCl
I-332I-332 4-nitrophenyl4-nitrophenyl CH 3 CH3 SCH 3 SCH 3 Ff Ff
I-333I-333 4-nitrophenyl4-nitrophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CH 3 CH3
I-334I-334 4-nitrophenyl4-nitrophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CF 3 CF 3
I-335I-335 4-nitrophenyl4-nitrophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCF 3 OCF 3
I-336I-336 4-nitrophenyl4-nitrophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCHF 2 OCHF 2
I-337I-337 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 ClCl II II
I-338I-338 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 ClCl BrBr BrBr
I-339I-339 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 ClCl ClCl ClCl
I-340I-340 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 ClCl Ff Ff
I-341I-341 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 ClCl BrBr CH 3 CH3
I-342I-342 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 ClCl BrBr CF 3 CF 3
I-343I-343 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 ClCl BrBr OCF 3 OCF 3
I-344I-344 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 ClCl BrBr OCHF 2 OCHF 2
I-345I-345 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 BrBr II II
I-346I-346 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 BrBr BrBr BrBr
I-347I-347 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 BrBr ClCl ClCl
I-348I-348 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 BrBr Ff Ff
I-349I-349 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 BrBr BrBr CH 3 CH3
I-350I-350 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-351I-351 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-352I-352 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
I-353I-353 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 II II
I-354I-354 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr BrBr
I-355I-355 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 ClCl ClCl
I-356I-356 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 Ff Ff
I-357I-357 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr CH 3 CH3
I-358I-358 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr CF 3 CF 3
I-359I-359 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCF 3 OCF 3
I-360I-360 4-difluoromethoxyphenyl4-difluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCHF 2 OCHF 2
I-361I-361 4-chlorophenyl4-chlorophenyl CH 3 CH3 ClCl II II
I-362I-362 4-chlorophenyl4-chlorophenyl CH 3 CH3 ClCl BrBr BrBr
I-363I-363 4-chlorophenyl4-chlorophenyl CH 3 CH3 ClCl ClCl ClCl
I-364I-364 4-chlorophenyl4-chlorophenyl CH 3 CH3 ClCl Ff Ff
I-365I-365 4-chlorophenyl4-chlorophenyl CH 3 CH3 ClCl BrBr CH 3 CH3
I-366I-366 4-chlorophenyl4-chlorophenyl CH 3 CH3 ClCl BrBr CF 3 CF 3
I-367I-367 4-chlorophenyl4-chlorophenyl CH 3 CH3 ClCl BrBr OCF 3 OCF 3
I-368I-368 4-chlorophenyl4-chlorophenyl CH 3 CH3 ClCl BrBr OCHF 2 OCHF 2
I-369I-369 4-chlorophenyl4-chlorophenyl CH 3 CH3 BrBr II II
I-370I-370 4-chlorophenyl4-chlorophenyl CH 3 CH3 BrBr BrBr BrBr
I-371I-371 4-chlorophenyl4-chlorophenyl CH 3 CH3 BrBr ClCl ClCl
I-372I-372 4-chlorophenyl4-chlorophenyl CH 3 CH3 BrBr Ff Ff
I-373I-373 4-chlorophenyl4-chlorophenyl CH 3 CH3 BrBr BrBr CH 3 CH3
I-374I-374 4-chlorophenyl4-chlorophenyl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-375I-375 4-chlorophenyl4-chlorophenyl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-376I-376 4-chlorophenyl4-chlorophenyl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
I-377I-377 4-chlorophenyl4-chlorophenyl CH 3 CH3 SCH 3 SCH 3 II II
I-378I-378 4-chlorophenyl4-chlorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr BrBr
I-379I-379 4-chlorophenyl4-chlorophenyl CH 3 CH3 SCH 3 SCH 3 ClCl ClCl
I-380I-380 4-chlorophenyl4-chlorophenyl CH 3 CH3 SCH 3 SCH 3 Ff Ff
I-381I-381 4-chlorophenyl4-chlorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CH 3 CH3
I-382I-382 4-chlorophenyl4-chlorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CF 3 CF 3
I-383I-383 4-chlorophenyl4-chlorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCF 3 OCF 3
I-384I-384 4-chlorophenyl4-chlorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCHF 2 OCHF 2
I-385I-385 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 ClCl II II
I-386I-386 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 ClCl BrBr BrBr
I-387I-387 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 ClCl ClCl ClCl
I-388I-388 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 ClCl Ff Ff
I-389I-389 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 ClCl BrBr CH 3 CH3
I-390I-390 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 ClCl BrBr CF 3 CF 3
I-391I-391 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 ClCl BrBr OCF 3 OCF 3
I-392I-392 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 ClCl BrBr OCHF 2 OCHF 2
I-393I-393 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 BrBr II II
I-394I-394 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 BrBr BrBr BrBr
I-395I-395 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 BrBr ClCl ClCl
I-396I-396 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 BrBr Ff Ff
I-397I-397 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 BrBr BrBr CH 3 CH3
I-398I-398 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-399I-399 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-400I-400 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
I-401I-401 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 SCH 3 SCH 3 II II
I-402I-402 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 SCH 3 SCH 3 BrBr BrBr
I-403I-403 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 SCH 3 SCH 3 ClCl ClCl
I-404I-404 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 SCH 3 SCH 3 Ff Ff
I-405I-405 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 SCH 3 SCH 3 BrBr CH 3 CH3
I-406I-406 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 SCH 3 SCH 3 BrBr CF 3 CF 3
I-407I-407 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCF 3 OCF 3
I-408I-408 3-trifluoromethylphenyl3-trifluoromethylphenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCHF 2 OCHF 2
I-409I-409 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 ClCl II II
I-410I-410 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 ClCl BrBr BrBr
I-411I-411 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 ClCl ClCl ClCl
I-412I-412 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 ClCl Ff Ff
I-413I-413 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 ClCl BrBr CH 3 CH3
I-414I-414 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 ClCl BrBr CF 3 CF 3
I-415I-415 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 ClCl BrBr OCF 3 OCF 3
I-416I-416 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 ClCl BrBr OCHF 2 OCHF 2
I-417I-417 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 BrBr II II
I-418I-418 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 BrBr BrBr BrBr
I-419I-419 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 BrBr ClCl ClCl
I-420I-420 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 BrBr Ff Ff
I-421I-421 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 BrBr BrBr CH 3 CH3
I-422I-422 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-423I-423 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-424I-424 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
I-425I-425 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 II II
I-426I-426 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr BrBr
I-427I-427 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 ClCl ClCl
I-428I-428 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 Ff Ff
I-429I-429 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr CH 3 CH3
I-430I-430 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr CF 3 CF 3
I-431I-431 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCF 3 OCF 3
I-432I-432 3-trifluoromethoxyphenyl3-trifluoromethoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCHF 2 OCHF 2
I-433I-433 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 ClCl II II
I-434I-434 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 ClCl BrBr BrBr
I-435I-435 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 ClCl ClCl ClCl
I-436I-436 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 ClCl Ff Ff
I-437I-437 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 ClCl BrBr CH 3 CH3
I-438I-438 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 ClCl BrBr CF 3 CF 3
I-439I-439 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 ClCl BrBr OCF 3 OCF 3
I-440I-440 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 ClCl BrBr OCHF 2 OCHF 2
I-441I-441 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 BrBr II II
I-442I-442 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 BrBr BrBr BrBr
I-443I-443 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 BrBr ClCl ClCl
I-444I-444 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 BrBr Ff Ff
I-445I-445 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 BrBr BrBr CH 3 CH3
I-446I-446 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-447I-447 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-448I-448 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
I-449I-449 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 SCH 3 SCH 3 II II
I-450I-450 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr BrBr
I-451I-451 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 SCH 3 SCH 3 ClCl ClCl
I-452I-452 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 SCH 3 SCH 3 Ff Ff
I-453I-453 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr CH 3 CH3
I-454I-454 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr CF 3 CF 3
I-455I-455 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCF 3 OCF 3
I-456I-456 3-methoxyphenyl3-methoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCHF 2 OCHF 2
I-457I-457 3-chlorophenyl3-chlorophenyl CH 3 CH3 ClCl II II
I-458I-458 3-chlorophenyl3-chlorophenyl CH 3 CH3 ClCl BrBr BrBr
I-459I-459 3-chlorophenyl3-chlorophenyl CH 3 CH3 ClCl ClCl ClCl
I-460I-460 3-chlorophenyl3-chlorophenyl CH 3 CH3 ClCl Ff Ff
I-461I-461 3-chlorophenyl3-chlorophenyl CH 3 CH3 ClCl BrBr CH 3 CH3
I-462I-462 3-chlorophenyl3-chlorophenyl CH 3 CH3 ClCl BrBr CF 3 CF 3
I-463I-463 3-chlorophenyl3-chlorophenyl CH 3 CH3 ClCl BrBr OCF 3 OCF 3
I-464I-464 3-chlorophenyl3-chlorophenyl CH 3 CH3 ClCl BrBr OCHF 2 OCHF 2
I-465I-465 3-chlorophenyl3-chlorophenyl CH 3 CH3 BrBr II II
I-466I-466 3-chlorophenyl3-chlorophenyl CH 3 CH3 BrBr BrBr BrBr
I-467I-467 3-chlorophenyl3-chlorophenyl CH 3 CH3 BrBr ClCl ClCl
I-468I-468 3-chlorophenyl3-chlorophenyl CH 3 CH3 BrBr Ff Ff
I-469I-469 3-chlorophenyl3-chlorophenyl CH 3 CH3 BrBr BrBr CH 3 CH3
I-470I-470 3-chlorophenyl3-chlorophenyl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-471I-471 3-chlorophenyl3-chlorophenyl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-472I-472 3-chlorophenyl3-chlorophenyl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
I-473I-473 3-chlorophenyl3-chlorophenyl CH 3 CH3 SCH 3 SCH 3 II II
I-474I-474 3-chlorophenyl3-chlorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr BrBr
I-475I-475 3-chlorophenyl3-chlorophenyl CH 3 CH3 SCH 3 SCH 3 ClCl ClCl
I-476I-476 3-chlorophenyl3-chlorophenyl CH 3 CH3 SCH 3 SCH 3 Ff Ff
I-477I-477 3-chlorophenyl3-chlorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CH 3 CH3
I-478I-478 3-chlorophenyl3-chlorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CF 3 CF 3
I-479I-479 3-chlorophenyl3-chlorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCF 3 OCF 3
I-480I-480 3-chlorophenyl3-chlorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCHF 2 OCHF 2
I-481I-481 3-cyanophenyl3-cyanophenyl CH 3 CH3 ClCl II II
I-482I-482 3-cyanophenyl3-cyanophenyl CH 3 CH3 ClCl BrBr BrBr
I-483I-483 3-cyanophenyl3-cyanophenyl CH 3 CH3 ClCl ClCl ClCl
I-484I-484 3-cyanophenyl3-cyanophenyl CH 3 CH3 ClCl Ff Ff
I-485I-485 3-cyanophenyl3-cyanophenyl CH 3 CH3 ClCl BrBr CH 3 CH3
I-486I-486 3-cyanophenyl3-cyanophenyl CH 3 CH3 ClCl BrBr CF 3 CF 3
I-487I-487 3-cyanophenyl3-cyanophenyl CH 3 CH3 ClCl BrBr OCF 3 OCF 3
I-488I-488 3-cyanophenyl3-cyanophenyl CH 3 CH3 ClCl BrBr OCHF 2 OCHF 2
I-489I-489 3-cyanophenyl3-cyanophenyl CH 3 CH3 BrBr II II
I-490I-490 3-cyanophenyl3-cyanophenyl CH 3 CH3 BrBr BrBr BrBr
I-491I-491 3-cyanophenyl3-cyanophenyl CH 3 CH3 BrBr ClCl ClCl
I-492I-492 3-cyanophenyl3-cyanophenyl CH 3 CH3 BrBr Ff Ff
I-493I-493 3-cyanophenyl3-cyanophenyl CH 3 CH3 BrBr BrBr CH 3 CH3
I-494I-494 3-cyanophenyl3-cyanophenyl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-495I-495 3-cyanophenyl3-cyanophenyl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-496I-496 3-cyanophenyl3-cyanophenyl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
I-497I-497 3-cyanophenyl3-cyanophenyl CH 3 CH3 SCH 3 SCH 3 II II
I-498I-498 3-cyanophenyl3-cyanophenyl CH 3 CH3 SCH 3 SCH 3 BrBr BrBr
I-499I-499 3-cyanophenyl3-cyanophenyl CH 3 CH3 SCH 3 SCH 3 ClCl ClCl
I-500I-500 3-cyanophenyl3-cyanophenyl CH 3 CH3 SCH 3 SCH 3 Ff Ff
I-501I-501 3-cyanophenyl3-cyanophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CH 3 CH3
I-502I-502 3-cyanophenyl3-cyanophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CF 3 CF 3
I-503I-503 3-cyanophenyl3-cyanophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCF 3 OCF 3
I-504I-504 3-cyanophenyl3-cyanophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCHF 2 OCHF 2
I-505I-505 2-fluorophenyl2-fluorophenyl CH 3 CH3 ClCl II II
I-506I-506 2-fluorophenyl2-fluorophenyl CH 3 CH3 ClCl BrBr BrBr
I-507I-507 2-fluorophenyl2-fluorophenyl CH 3 CH3 ClCl ClCl ClCl
I-508I-508 2-fluorophenyl2-fluorophenyl CH 3 CH3 ClCl Ff Ff
I-509I-509 2-fluorophenyl2-fluorophenyl CH 3 CH3 ClCl BrBr CH 3 CH3
I-510I-510 2-fluorophenyl2-fluorophenyl CH 3 CH3 ClCl BrBr CF 3 CF 3
I-511I-511 2-fluorophenyl2-fluorophenyl CH 3 CH3 ClCl BrBr OCF 3 OCF 3
I-512I-512 2-fluorophenyl2-fluorophenyl CH 3 CH3 ClCl BrBr OCHF 2 OCHF 2
I-513I-513 2-fluorophenyl2-fluorophenyl CH 3 CH3 BrBr II II
I-514I-514 2-fluorophenyl2-fluorophenyl CH 3 CH3 BrBr BrBr BrBr
I-515I-515 2-fluorophenyl2-fluorophenyl CH 3 CH3 BrBr ClCl ClCl
I-516I-516 2-fluorophenyl2-fluorophenyl CH 3 CH3 BrBr Ff Ff
I-517I-517 2-fluorophenyl2-fluorophenyl CH 3 CH3 BrBr BrBr CH 3 CH3
I-518I-518 2-fluorophenyl2-fluorophenyl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-519I-519 2-fluorophenyl2-fluorophenyl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-520I-520 2-fluorophenyl2-fluorophenyl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
I-521I-521 2-fluorophenyl2-fluorophenyl CH 3 CH3 SCH 3 SCH 3 II II
I-522I-522 2-fluorophenyl2-fluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr BrBr
I-523I-523 2-fluorophenyl2-fluorophenyl CH 3 CH3 SCH 3 SCH 3 ClCl ClCl
I-524I-524 2-fluorophenyl2-fluorophenyl CH 3 CH3 SCH 3 SCH 3 Ff Ff
I-525I-525 2-fluorophenyl2-fluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CH 3 CH3
I-526I-526 2-fluorophenyl2-fluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CF 3 CF 3
I-527I-527 2-fluorophenyl2-fluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCF 3 OCF 3
I-528I-528 2-fluorophenyl2-fluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCHF 2 OCHF 2
I-529I-529 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 ClCl II II
I-530I-530 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 ClCl BrBr BrBr
I-531I-531 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 ClCl ClCl ClCl
I-532I-532 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 ClCl Ff Ff
I-533I-533 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 ClCl BrBr CH 3 CH3
I-534I-534 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 ClCl BrBr CF 3 CF 3
I-535I-535 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 ClCl BrBr OCF 3 OCF 3
I-536I-536 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 ClCl BrBr OCHF 2 OCHF 2
I-537I-537 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 BrBr II II
I-538I-538 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 BrBr BrBr BrBr
I-539I-539 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 BrBr ClCl ClCl
I-540I-540 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 BrBr Ff Ff
I-541I-541 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 BrBr BrBr CH 3 CH3
I-542I-542 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-543I-543 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-544I-544 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
I-545I-545 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 SCH 3 SCH 3 II II
I-546I-546 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr BrBr
I-547I-547 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 SCH 3 SCH 3 ClCl ClCl
I-548I-548 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 SCH 3 SCH 3 Ff Ff
I-549I-549 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr CH 3 CH3
I-550I-550 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr CF 3 CF 3
I-551I-551 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCF 3 OCF 3
I-552I-552 2-methoxyphenyl2-methoxyphenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCHF 2 OCHF 2
I-553I-553 3, 5-difluorophenyl3, 5-difluorophenyl CH 3 CH3 ClCl II II
I-554I-554 3, 5-difluorophenyl3, 5-difluorophenyl CH 3 CH3 ClCl BrBr BrBr
I-555I-555 3, 5-difluorophenyl3, 5-difluorophenyl CH 3 CH3 ClCl ClCl ClCl
I-556I-556 3, 5-difluorophenyl3, 5-difluorophenyl CH 3 CH3 ClCl Ff Ff
I-557I-557 3, 5-difluorophenyl3, 5-difluorophenyl CH 3 CH3 ClCl BrBr CH 3 CH3
I-558I-558 3, 5-difluorophenyl3, 5-difluorophenyl CH 3 CH3 ClCl BrBr CF 3 CF 3
I-559I-559 3, 5-difluorophenyl3, 5-difluorophenyl CH 3 CH3 ClCl BrBr OCF 3 OCF 3
I-560I-560 3, 5-difluorophenyl3, 5-difluorophenyl CH 3 CH3 ClCl BrBr OCHF 2 OCHF 2
I-561I-561 3, 5-difluorophenyl3, 5-difluorophenyl CH 3 CH3 BrBr II II
I-562I-562 3, 5-difluorophenyl3, 5-difluorophenyl CH 3 CH3 BrBr BrBr BrBr
I-563I-563 3, 5-difluorophenyl3, 5-difluorophenyl CH 3 CH3 BrBr ClCl ClCl
I-564I-564 3, 5-difluorophenyl3, 5-difluorophenyl CH 3 CH3 BrBr Ff Ff
I-565I-565 3, 5-difluorophenyl3, 5-difluorophenyl CH 3 CH3 BrBr BrBr CH 3 CH3
I-566I-566 3, 5-difluorophenyl3, 5-difluorophenyl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-567I-567 3, 5-difluorophenyl3, 5-difluorophenyl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-568I-568 3, 5-difluorophenyl3, 5-difluorophenyl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
I-569I-569 3, 5-difluorophenyl3, 5-difluorophenyl CH 3 CH3 SCH 3 SCH 3 II II
I-570I-570 3, 5-difluorophenyl3, 5-difluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr BrBr
I-571I-571 3, 5-difluorophenyl3, 5-difluorophenyl CH 3 CH3 SCH 3 SCH 3 ClCl ClCl
I-572I-572 3, 5-difluorophenyl3, 5-difluorophenyl CH 3 CH3 SCH 3 SCH 3 Ff Ff
I-573I-573 3, 5-difluorophenyl3, 5-difluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CH 3 CH3
I-574I-574 3, 5-difluorophenyl3, 5-difluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CF 3 CF 3
I-575I-575 3,5-difluorophenyl3,5-difluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCF 3 OCF 3
I-576I-576 3,5-difluorophenyl3,5-difluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCHF 2 OCHF 2
I-577I-577 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 ClCl II II
I-578I-578 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 ClCl BrBr BrBr
I-579I-579 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 ClCl ClCl ClCl
I-580I-580 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 ClCl Ff Ff
I-581I-581 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 ClCl BrBr CH 3 CH3
I-582I-582 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 ClCl BrBr CF 3 CF 3
I-583I-583 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 ClCl BrBr OCF 3 OCF 3
I-584I-584 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 ClCl BrBr OCHF 2 OCHF 2
I-585I-585 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 BrBr II II
I-586I-586 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 BrBr BrBr BrBr
I-587I-587 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 BrBr ClCl ClCl
I-588I-588 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 BrBr Ff Ff
I-589I-589 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 BrBr BrBr CH 3 CH3
I-590I-590 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-591I-591 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-592I-592 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
I-593I-593 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 SCH 3 SCH 3 II II
I-594I-594 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr BrBr
I-595I-595 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 SCH 3 SCH 3 ClCl ClCl
I-596I-596 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 SCH 3 SCH 3 Ff Ff
I-597I-597 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CH 3 CH3
I-598I-598 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CF 3 CF 3
I-599I-599 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCF 3 OCF 3
I-600I-600 3,4,5-trifluorophenyl3,4,5-trifluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCHF 2 OCHF 2
I-601I-601 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 SCH 3 SCH 3 II II
I-602I-602 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr BrBr
I-603I-603 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 SCH 3 SCH 3 ClCl ClCl
I-604I-604 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 SCH 3 SCH 3 Ff Ff
I-605I-605 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CH 3 CH3
I-606I-606 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CF 3 CF 3
I-607I-607 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCF 3 OCF 3
I-608I-608 3,4-difluorophenyl3,4-difluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCHF 2 OCHF 2
I-609I-609 4-fluorophenyl4-fluorophenyl CH 3 CH3 SCH 3 SCH 3 II II
I-610I-610 4-fluorophenyl4-fluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr BrBr
I-611I-611 4-fluorophenyl4-fluorophenyl CH 3 CH3 SCH 3 SCH 3 ClCl ClCl
I-612I-612 4-fluorophenyl4-fluorophenyl CH 3 CH3 SCH 3 SCH 3 Ff Ff
I-613I-613 4-fluorophenyl4-fluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CH 3 CH3
I-614I-614 4-fluorophenyl4-fluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr CF 3 CF 3
I-615I-615 4-fluorophenyl4-fluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCF 3 OCF 3
I-616I-616 4-fluorophenyl4-fluorophenyl CH 3 CH3 SCH 3 SCH 3 BrBr OCHF 2 OCHF 2
I-617I-617 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 SC 2H 5 SC 2 H 5 BrBr CF 3 CF 3
I-618I-618 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 SC 2H 5 SC 2 H 5 BrBr OCHF 2 OCHF 2
I-619I-619 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 1H-1,2,4-triazol-1-yl1H-1,2,4-triazol-1-yl BrBr CF 3 CF 3
I-620I-620 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 1H-1,2,4-triazol-1-yl1H-1,2,4-triazol-1-yl BrBr OCHF 2 OCHF 2
I-621I-621 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 2H-1,2,3-triazol-2-yl2H-1,2,3-triazol-2-yl BrBr CF 3 CF 3
I-622I-622 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 2H-1,2,3-triazol-2-yl2H-1,2,3-triazol-2-yl BrBr OCHF 2 OCHF 2
I-623I-623 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 morpholin-4-ylmorpholin-4-yl BrBr CF 3 CF 3
I-624I-624 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 morpholin-4-ylmorpholin-4-yl BrBr OCHF 2 OCHF 2
I-625I-625 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 OC 2H 5 OC 2 H 5 BrBr CF 3 CF 3
I-626I-626 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 OC 2H 5 OC 2 H 5 BrBr OCHF 2 OCHF 2
I-627I-627 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 NHCH 3 NHCH 3 BrBr CF 3 CF 3
I-628I-628 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 NHCH 3 NHCH 3 BrBr OCHF 2 OCHF 2
I-629I-629 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 4-ethylpiperazin-1-yl4-ethylpiperazin-1-yl BrBr CF 3 CF 3
I-630I-630 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 4-ethylpiperazin-1-yl4-ethylpiperazin-1-yl BrBr OCHF 2 OCHF 2
I-631I-631 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 SC(CH 3) 3 SC(CH 3 ) 3 BrBr CF 3 CF 3
I-632I-632 2,2-difluorobenzo[d][1,3]dioxol-5-yl2,2-difluorobenzo[d][1,3]dioxol-5-yl CH 3 CH3 SC(CH 3) 3 SC(CH 3 ) 3 BrBr OCHF 2 OCHF 2
I-633I-633 4-cyanophenyl4-cyanophenyl CH 3 CH3 SC 2H 5 SC 2 H 5 BrBr CF 3 CF 3
I-634I-634 4-cyanophenyl4-cyanophenyl CH 3 CH3 SC 2H 5 SC 2 H 5 BrBr OCHF 2 OCHF 2
I-635I-635 4-cyanophenyl4-cyanophenyl CH 3 CH3 1H-1,2,4-triazol-1-yl1H-1,2,4-triazol-1-yl BrBr CF 3 CF 3
I-636I-636 4-cyanophenyl4-cyanophenyl CH 3 CH3 1H-1,2,4-triazol-1-yl1H-1,2,4-triazol-1-yl BrBr OCHF 2 OCHF 2
I-637I-637 4-cyanophenyl4-cyanophenyl CH 3 CH3 2H-1,2,3-triazol-2-yl2H-1,2,3-triazol-2-yl BrBr CF 3 CF 3
I-638I-638 4-cyanophenyl4-cyanophenyl CH 3 CH3 2H-1,2,3-triazol-2-yl2H-1,2,3-triazol-2-yl BrBr OCHF 2 OCHF 2
I-639I-639 4-cyanophenyl4-cyanophenyl CH 3 CH3 morpholin-4-ylmorpholin-4-yl BrBr CF 3 CF 3
I-640I-640 4-cyanophenyl4-cyanophenyl CH 3 CH3 morpholin-4-ylmorpholin-4-yl BrBr OCHF 2 OCHF 2
I-641I-641 4-cyanophenyl4-cyanophenyl CH 3 CH3 OC 2H 5 OC 2 H 5 BrBr CF 3 CF 3
I-642I-642 4-cyanophenyl4-cyanophenyl CH 3 CH3 OC 2H 5 OC 2 H 5 BrBr OCHF 2 OCHF 2
I-643I-643 4-cyanophenyl4-cyanophenyl CH 3 CH3 NHCH 3 NHCH 3 BrBr CF 3 CF 3
I-644I-644 4-cyanophenyl4-cyanophenyl CH 3 CH3 NHCH 3 NHCH 3 BrBr OCHF 2 OCHF 2
I-645I-645 4-cyanophenyl4-cyanophenyl CH 3 CH3 4-ethylpiperazin-1-yl4-ethylpiperazin-1-yl BrBr CF 3 CF 3
I-646I-646 4-cyanophenyl4-cyanophenyl CH 3 CH3 4-ethylpiperazin-1-yl4-ethylpiperazin-1-yl BrBr OCHF 2 OCHF 2
I-647I-647 4-cyanophenyl4-cyanophenyl CH 3 CH3 SC(CH 3) 3 SC(CH 3 ) 3 BrBr CF 3 CF 3
I-648I-648 4-cyanophenyl4-cyanophenyl CH 3 CH3 SC(CH 3) 3 SC(CH 3 ) 3 BrBr OCHF 2 OCHF 2
I-649I-649 4-fluorophenyl4-fluorophenyl CH 3 CH3 SC 2H 5 SC 2 H 5 BrBr CF 3 CF 3
I-650I-650 4-fluorophenyl4-fluorophenyl CH 3 CH3 SC 2H 5 SC 2 H 5 BrBr OCHF 2 OCHF 2
I-651I-651 4-fluorophenyl4-fluorophenyl CH 3 CH3 1H-1,2,4-triazol-1-yl1H-1,2,4-triazol-1-yl BrBr CF 3 CF 3
I-652I-652 4-fluorophenyl4-fluorophenyl CH 3 CH3 1H-1,2,4-triazol-1-yl1H-1,2,4-triazol-1-yl BrBr OCHF 2 OCHF 2
I-653I-653 4-fluorophenyl4-fluorophenyl CH 3 CH3 2H-1,2,3-triazol-2-yl2H-1,2,3-triazol-2-yl BrBr CF 3 CF 3
I-654I-654 4-fluorophenyl4-fluorophenyl CH 3 CH3 2H-1,2,3-triazol-2-yl2H-1,2,3-triazol-2-yl BrBr OCHF 2 OCHF 2
I-655I-655 4-fluorophenyl4-fluorophenyl CH 3 CH3 morpholin-4-ylmorpholin-4-yl BrBr CF 3 CF 3
I-656I-656 4-fluorophenyl4-fluorophenyl CH 3 CH3 morpholin-4-ylmorpholin-4-yl BrBr OCHF 2 OCHF 2
I-657I-657 4-fluorophenyl4-fluorophenyl CH 3 CH3 OC 2H 5 OC 2 H 5 BrBr CF 3 CF 3
I-658I-658 4-fluorophenyl4-fluorophenyl CH 3 CH3 OC 2H 5 OC 2 H 5 BrBr OCHF 2 OCHF 2
I-659I-659 4-fluorophenyl4-fluorophenyl CH 3 CH3 NHCH 3 NHCH 3 BrBr CF 3 CF 3
I-660I-660 4-fluorophenyl4-fluorophenyl CH 3 CH3 NHCH 3 NHCH 3 BrBr OCHF 2 OCHF 2
I-661I-661 4-fluorophenyl4-fluorophenyl CH 3 CH3 4-ethylpiperazin-1-yl4-ethylpiperazin-1-yl BrBr CF 3 CF 3
I-662I-662 4-fluorophenyl4-fluorophenyl CH 3 CH3 4-ethylpiperazin-1-yl4-ethylpiperazin-1-yl BrBr OCHF 2 OCHF 2
I-663I-663 4-fluorophenyl4-fluorophenyl CH 3 CH3 SC(CH 3) 3 SC(CH 3 ) 3 BrBr CF 3 CF 3
I-664I-664 4-fluorophenyl4-fluorophenyl CH 3 CH3 SC(CH 3) 3 SC(CH 3 ) 3 BrBr OCHF 2 OCHF 2
I-665I-665 4-trifluoromethylphenyl4-trifluoromethylphenyl CH 3 CH3 SC 2H 5 SC 2 H 5 BrBr CF 3 CF 3
I-666I-666 4-trifluoromethylphenyl4-trifluoromethylphenyl CH 3 CH3 SC 2H 5 SC 2 H 5 BrBr OCHF 2 OCHF 2
I-667I-667 4-trifluoromethylphenyl4-trifluoromethylphenyl CH 3 CH3 1H-1,2,4-triazol-1-yl1H-1,2,4-triazol-1-yl BrBr CF 3 CF 3
I-668I-668 4-trifluoromethylphenyl4-trifluoromethylphenyl CH 3 CH3 1H-1,2,4-triazol-1-yl1H-1,2,4-triazol-1-yl BrBr OCHF 2 OCHF 2
I-669I-669 4-trifluoromethylphenyl4-trifluoromethylphenyl CH 3 CH3 2H-1,2,3-triazol-2-yl2H-1,2,3-triazol-2-yl BrBr CF 3 CF 3
I-670I-670 4-trifluoromethylphenyl4-trifluoromethylphenyl CH 3 CH3 2H-1,2,3-triazol-2-yl2H-1,2,3-triazol-2-yl BrBr OCHF 2 OCHF 2
I-671I-671 4-trifluoromethylphenyl4-trifluoromethylphenyl CH 3 CH3 morpholin-4-ylmorpholin-4-yl BrBr CF 3 CF 3
I-672I-672 4-trifluoromethylphenyl4-trifluoromethylphenyl CH 3 CH3 morpholin-4-ylmorpholin-4-yl BrBr OCHF 2 OCHF 2
I-673I-673 4-trifluoromethylphenyl4-trifluoromethylphenyl CH 3 CH3 OC 2H 5 OC 2 H 5 BrBr CF 3 CF 3
I-674I-674 4-trifluoromethylphenyl4-trifluoromethylphenyl CH 3 CH3 OC 2H 5 OC 2 H 5 BrBr OCHF 2 OCHF 2
I-675I-675 4-trifluoromethylphenyl4-trifluoromethylphenyl CH 3 CH3 NHCH 3 NHCH 3 BrBr CF 3 CF 3
I-676I-676 4-trifluoromethylphenyl4-trifluoromethylphenyl CH 3 CH3 NHCH 3 NHCH 3 BrBr OCHF 2 OCHF 2
I-677I-677 4-trifluoromethylphenyl4-trifluoromethylphenyl CH 3 CH3 4-ethylpiperazin-1-yl4-ethylpiperazin-1-yl BrBr CF 3 CF 3
I-678I-678 4-trifluoromethylphenyl4-trifluoromethylphenyl CH 3 CH3 4-ethylpiperazin-1-yl4-ethylpiperazin-1-yl BrBr OCHF 2 OCHF 2
I-679I-679 4-trifluoromethylphenyl4-trifluoromethylphenyl CH 3 CH3 SC(CH 3) 3 SC(CH 3 ) 3 BrBr CF 3 CF 3
I-680I-680 4-trifluoromethylphenyl4-trifluoromethylphenyl CH 3 CH3 SC(CH 3) 3 SC(CH 3 ) 3 BrBr OCHF 2 OCHF 2
I-681I-681 4-cyanophenyl4-cyanophenyl CH 3 CH3 BrBr II II
I-682I-682 4-cyanophenyl4-cyanophenyl CH 3 CH3 BrBr BrBr BrBr
I-683I-683 4-cyanophenyl4-cyanophenyl CH 3 CH3 BrBr ClCl ClCl
I-684I-684 4-cyanophenyl4-cyanophenyl CH 3 CH3 BrBr Ff Ff
I-685I-685 4-cyanophenyl4-cyanophenyl CH 3 CH3 BrBr BrBr CH 3 CH3
I-686I-686 4-cyanophenyl4-cyanophenyl CH 3 CH3 BrBr BrBr CF 3 CF 3
I-687I-687 4-cyanophenyl4-cyanophenyl CH 3 CH3 BrBr BrBr OCF 3 OCF 3
I-688I-688 4-cyanophenyl4-cyanophenyl CH 3 CH3 BrBr BrBr OCHF 2 OCHF 2
部分化合物的 1H NMR(600MHz,CDCl 3,ppm)及物化性质如下： The 1 H NMR (600MHz, CDCl 3 , ppm) and physical and chemical properties of some compounds are as follows:
Figure PCTCN2022118920-appb-000012
Figure PCTCN2022118920-appb-000012
Figure PCTCN2022118920-appb-000013
Figure PCTCN2022118920-appb-000013
在有机分子中，由于取代基的电负性、体积大小或空间构型的不同，整个分子在昆虫和植物等生物体内的输导性能或与受体结合差异性会很大，表现出的生物活性差异也会有很大， 而分子的输导性能和与受体结合的合适性是不可预测的，需要大量的创造性劳动才能获知。In organic molecules, due to the difference in electronegativity, size or spatial configuration of substituents, the conduction performance or binding to receptors of the whole molecule in organisms such as insects and plants will vary greatly, showing biological Activity can also vary widely, and a molecule's transport properties and suitability for receptor binding are unpredictable and require a great deal of creative effort to learn.
本发明的新型亚胺类衍生物(通式I化合物)具有优异的杀虫和杀螨活性，可以防治如下害虫：鳞翅目害虫，如粘虫、甜菜夜蛾和小菜蛾等；同翅目害虫，如桃蚜、叶婵和飞虱等；半翅目害虫，如玉米长蝽、番茄盲蝽和稻臭椿等；缨翅目害虫，如棉蓟马、苜蓿蓟马和黄豆蓟马、西花蓟马等；鞘翅目害虫，如马铃薯甲虫和叩甲等；双翅目害虫，如蝇和蚊等；膜翅目害虫，如蜂和蚁等。可以防治如下害螨：叶螨科(二斑叶螨、朱砂叶螨、苹果全爪螨、柑橘全爪螨等)、瘿螨科、跗线螨科等。因此，本发明还包括通式I化合物用于农业、林业及卫生领域中控制虫害和螨害的用途。The novel imine derivatives (compound of general formula I) of the present invention have excellent insecticidal and acaricidal activities, and can control the following pests: Lepidoptera pests, such as armyworm, beet armyworm and diamondback moth, etc.; Homoptera Pests, such as green peach aphid, leaf-chan and planthopper, etc.; Hemiptera pests, such as corn long bug, tomato mirid bug and rice ailanthus, etc.; Thysanoptera pests, such as cotton thrips, alfalfa thrips and soybean thrips, Western Flower thrips, etc.; Coleoptera pests, such as potato beetles and clam beetles; Diptera pests, such as flies and mosquitoes; Hymenoptera pests, such as bees and ants. It can prevent and control the following harmful mites: Tetranychidae (Tetranychus urticae, Tetranychus cinnabarinidae, Panonychus apple, Panonychus citrus, etc.), Eriodidae, Tarsalidae, etc. Therefore, the present invention also includes the use of the compound of general formula I for controlling insect pests and acarids in the fields of agriculture, forestry and hygiene.
本发明的技术方案还包括防治害虫的方法：将本发明的杀虫化合物施于所述的害虫或其生长介质上。通常选择的较为适宜有效量为每公顷10克到1000克，优选有效量为每公顷20克到500克。The technical scheme of the present invention also includes a method for controlling pests: applying the pesticidal compound of the present invention to the pests or their growth medium. Usually, the more suitable effective dose is 10 grams to 1000 grams per hectare, and the preferred effective dose is 20 grams to 500 grams per hectare.
本发明的技术方案还包括防治害螨的方法：将本发明的杀虫化合物施于所述的害螨或其生长介质上。通常选择的较为适宜有效量为每公顷10克到1000克，优选有效量为每公顷20克到500克。The technical solution of the present invention also includes a method for controlling harmful mites: applying the insecticidal compound of the present invention to the harmful mites or their growth medium. Usually, the more suitable effective dose is 10 grams to 1000 grams per hectare, and the preferred effective dose is 20 grams to 500 grams per hectare.
应该明确的是，在本发明的权利要求所限定的范围内，可以进行各种变换和改动。It should be understood that various changes and modifications can be made within the scope of the present invention defined by the claims.
本发明所具有的优点：The advantages that the present invention has:
本发明化合物结构新颖，兼具杀虫和杀螨，用途广泛。The compound of the invention is novel in structure, has both insecticidal and acaricidal properties, and has wide uses.
具体实施方式Detailed ways
以下具体实施例用来进一步说明本发明，但本发明绝非限于这些例子。The following specific examples are used to further illustrate the present invention, but the present invention is by no means limited to these examples.
合成实施例Synthetic example
实施例1：化合物I-38的制备Embodiment 1: the preparation of compound I-38
1)N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-2-氟-3-硝基苯甲酰胺的制备1) Preparation of N-(2-bromo-4-heptafluoroisopropyl-6-trifluoromethylphenyl)-2-fluoro-3-nitrobenzamide
Figure PCTCN2022118920-appb-000014
Figure PCTCN2022118920-appb-000014
向反应瓶中加入2-氟-3-硝基苯甲酸(8.23g，44.00mmol)、氯化亚砜(34.08g)和DMF(0.35g)，升温至80℃反应8小时，减压蒸出氯化亚砜，得到酰氯。向酰氯中加入1,3-二甲基-2-咪唑啉酮(130mL)、2-溴-6-三氟甲基-4-七氟异丙基苯胺(16.48g，40.00mmol)和碘化钾(1.68g，10.00mmol)，升温至100℃反应48小时。将反应液降至室温，过滤除去不溶物，加入乙酸乙酯(100mL)溶解，依次用饱和碳酸氢钠水溶液和饱和食盐水洗涤，分出有机相，将有机相用无水硫酸镁干燥，过滤后减压蒸出有机溶剂，残余物经柱色谱分离纯化得标题物，白色固体1.86g，收率为8％(以2-溴-4-七氟异丙基-6-三氟甲基苯胺计)。Add 2-fluoro-3-nitrobenzoic acid (8.23g, 44.00mmol), thionyl chloride (34.08g) and DMF (0.35g) into the reaction flask, raise the temperature to 80°C for 8 hours, and evaporate under reduced pressure Thionyl chloride gives acid chloride. To the acid chloride was added 1,3-dimethyl-2-imidazolinone (130 mL), 2-bromo-6-trifluoromethyl-4-heptafluoroisopropylaniline (16.48 g, 40.00 mmol) and potassium iodide ( 1.68g, 10.00mmol), heated to 100°C for 48 hours. The reaction solution was lowered to room temperature, filtered to remove insoluble matter, added ethyl acetate (100mL) to dissolve, washed with saturated aqueous sodium bicarbonate solution and saturated brine successively, separated the organic phase, dried the organic phase with anhydrous magnesium sulfate, filtered Afterwards, the organic solvent was evaporated under reduced pressure, and the residue was separated and purified by column chromatography to obtain the title product, 1.86 g of a white solid, with a yield of 8% (with 2-bromo-4-heptafluoroisopropyl-6-trifluoromethylaniline count).
1H NMR(600MHz,CDCl 3,ppm):8.47-8.42(m,1H),8.32-8.26(m,1H),8.21(d,1H),8.17(s,1H),7.94(s,1H),7.55-7.49(m,1H). 1 H NMR (600MHz, CDCl 3 , ppm): 8.47-8.42(m, 1H), 8.32-8.26(m, 1H), 8.21(d, 1H), 8.17(s, 1H), 7.94(s, 1H) ,7.55-7.49(m,1H).
2)N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-2-氟-3-氨基苯甲酰胺的制备2) Preparation of N-(2-bromo-4-heptafluoroisopropyl-6-trifluoromethylphenyl)-2-fluoro-3-aminobenzamide
Figure PCTCN2022118920-appb-000015
Figure PCTCN2022118920-appb-000015
向反应瓶中加入N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-2-氟-3-硝基苯甲酰胺(1.74g，3.00mmol)、二氧六环(10mL)和氯化亚锡二水合物(2.73g，12.00mmol)，缓慢滴入36％浓盐酸(3mL)。升温至65℃保温反应，TLC监测至反应完全。将反应体系冷却至室温，将反 应液倾入冰水(15mL)中，加入乙酸乙酯(30mL)，缓慢加入5％氢氧化钠水溶液中和至pH＝8-9。将析出的沉淀经硅藻土过滤后，用乙酸乙酯(10mL)洗涤滤饼，将滤液分层。将有机相用无水硫酸镁干燥，过滤后减压蒸出有机溶剂，残余物经柱色谱分离纯化得标题物，黄色固体1.46g，收率为88％(以N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-2-氟-3-硝基苯甲酰胺计)。Add N-(2-bromo-4-heptafluoroisopropyl-6-trifluoromethylphenyl)-2-fluoro-3-nitrobenzamide (1.74g, 3.00mmol), di Hexane (10 mL) and stannous chloride dihydrate (2.73 g, 12.00 mmol) were slowly added dropwise to 36% concentrated hydrochloric acid (3 mL). The temperature was raised to 65°C to keep the reaction, and the reaction was monitored by TLC until the reaction was complete. The reaction system was cooled to room temperature, the reaction solution was poured into ice water (15 mL), ethyl acetate (30 mL) was added, and 5% aqueous sodium hydroxide was added slowly to neutralize to pH=8-9. After the precipitate was filtered through celite, the filter cake was washed with ethyl acetate (10 mL), and the filtrate was separated into layers. The organic phase was dried with anhydrous magnesium sulfate, and after filtration, the organic solvent was evaporated under reduced pressure, and the residue was separated and purified by column chromatography to obtain the title product, 1.46 g of a yellow solid, and the yield was 88% (as N-(2-bromo-4 -heptafluoroisopropyl-6-trifluoromethylphenyl)-2-fluoro-3-nitrobenzamide).
1H NMR(60MHz,CDCl 3,ppm):8.29(d,1H),8.13(s,1H),7.91(s,1H),7.50-7.44(m,1H),7.12-7.07(m,1H),7.04-6.94(m,1H),3.93(s,br,2H). 1 H NMR(60MHz, CDCl 3 ,ppm):8.29(d,1H),8.13(s,1H),7.91(s,1H),7.50-7.44(m,1H),7.12-7.07(m,1H) ,7.04-6.94(m,1H),3.93(s,br,2H).
3)N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-2-氟-3-甲胺基苯甲酰胺的制备3) Preparation of N-(2-bromo-4-heptafluoroisopropyl-6-trifluoromethylphenyl)-2-fluoro-3-methylaminobenzamide
Figure PCTCN2022118920-appb-000016
Figure PCTCN2022118920-appb-000016
向反应瓶中加入98％浓硫酸(6mL)和N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-2-氟-3-氨基苯甲酰胺(1.10g，2.00mmol)，充分搅拌溶解。在30-35℃之间缓慢滴入含量37-40％甲醛水溶液(5mL)，滴毕，升温至40℃继续保温反应，TLC监测至反应完全。将反应体系冷却至室温，将反应液缓慢倾入冰水(20mL)中，充分搅拌，析出固体，过滤，滤饼经柱色谱分离纯化得标题物，白色固体1.02g，收率为90％(N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-2-氟-3-氨基苯甲酰胺)。Add 98% concentrated sulfuric acid (6 mL) and N-(2-bromo-4-heptafluoroisopropyl-6-trifluoromethylphenyl)-2-fluoro-3-aminobenzamide (1.10 g, 2.00mmol), fully stirred to dissolve. Slowly drop in 37-40% formaldehyde aqueous solution (5mL) at 30-35°C. After dropping, raise the temperature to 40°C to continue the heat preservation reaction. TLC monitors until the reaction is complete. The reaction system was cooled to room temperature, and the reaction solution was slowly poured into ice water (20 mL), fully stirred, and a solid was precipitated, filtered, and the filter cake was separated and purified by column chromatography to obtain the title product, 1.02 g of a white solid, and the yield was 90% ( N-(2-bromo-4-heptafluoroisopropyl-6-trifluoromethylphenyl)-2-fluoro-3-aminobenzamide).
1H NMR(600MHz,CDCl 3,ppm):8.28(d,1H),8.13(s,1H),7.90(s,1H),7.40-7.36(m,1H),7.19-7.14(m,1H),6.93-6.88(m,1H),4.13(s,br,1H),2.94(s,3H). 1 H NMR (600MHz, CDCl 3 , ppm): 8.28(d, 1H), 8.13(s, 1H), 7.90(s, 1H), 7.40-7.36(m, 1H), 7.19-7.14(m, 1H) ,6.93-6.88(m,1H),4.13(s,br,1H),2.94(s,3H).
4)N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-2-氟-3-(N-甲基-苯甲酰胺基)苯甲酰胺的制备4) Preparation of N-(2-bromo-4-heptafluoroisopropyl-6-trifluoromethylphenyl)-2-fluoro-3-(N-methyl-benzamido)benzamide
Figure PCTCN2022118920-appb-000017
Figure PCTCN2022118920-appb-000017
向反应瓶中加入甲苯(20mL)、苯甲酰氯(0.16g，1.11mmol)、N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-2-氟-3-甲胺基苯甲酰胺(0.56g，1.00mmol)升温至110℃反应，TLC监测至反应完全。将反应体系降温至室温，充分搅拌，逐渐析出固体，过滤，滤饼经柱色谱分离纯化得标题物，白色固体0.57g，收率为85％(以N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-2-氟-3-甲胺基苯甲酰胺计)。To the reaction flask was added toluene (20 mL), benzoyl chloride (0.16 g, 1.11 mmol), N-(2-bromo-4-heptafluoroisopropyl-6-trifluoromethylphenyl)-2-fluoro- 3-Methylaminobenzamide (0.56g, 1.00mmol) was heated to 110°C for reaction, and the reaction was monitored by TLC until the reaction was complete. The reaction system was cooled to room temperature, fully stirred, and the solid was gradually precipitated, filtered, and the filter cake was separated and purified by column chromatography to obtain the title product, 0.57 g of a white solid, and the yield was 85% (based on N-(2-bromo-4-heptafluoro (isopropyl-6-trifluoromethylphenyl)-2-fluoro-3-methylaminobenzamide).
1H NMR(600MHz,CDCl 3,ppm):8.12(s,1H),8.07-7.97(m,2H),7.90(s,1H),7.47-7.42(m,1H),7.33-7.19(m,6H),3.50(s,3H). 1 H NMR(600MHz, CDCl 3 ,ppm):8.12(s,1H),8.07-7.97(m,2H),7.90(s,1H),7.47-7.42(m,1H),7.33-7.19(m, 6H),3.50(s,3H).
5)N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-2-氟-3-(N-甲基-苯甲酰胺基)苯甲亚胺酰氯(化合物I-38)的制备5) N-(2-bromo-4-heptafluoroisopropyl-6-trifluoromethylphenyl)-2-fluoro-3-(N-methyl-benzamido) benzimide chloride ( Compound I-38) Preparation
Figure PCTCN2022118920-appb-000018
Figure PCTCN2022118920-appb-000018
向反应瓶中加入甲苯(5mL)、N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-2-氟-3-(N-甲基-苯甲酰胺基)苯甲酰胺(0.53g，0.79mmol)、三氯氧磷(5ml)、DMF(0.10g)升温至130℃反应，TLC监测至反应完全。将反应体系降温至室温，将反应液缓慢倾入大量冰水中，充分搅拌，用乙酸乙酯(30mL)溶解、萃取、分层，有机相依次用饱和碳酸氢钠水溶液和饱和食盐水洗涤，分出有机相，将有机相用无水硫酸镁干燥，过滤后减压蒸出有机溶剂，残余物经柱色谱分离纯化得标题物，白色固体0.35g，收率为64％(以N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-2-氟-3-(N-甲基-苯甲酰胺基)苯甲酰胺计)。To the reaction flask was added toluene (5 mL), N-(2-bromo-4-heptafluoroisopropyl-6-trifluoromethylphenyl)-2-fluoro-3-(N-methyl-benzamide Base) benzamide (0.53g, 0.79mmol), phosphorus oxychloride (5ml), DMF (0.10g) was heated to 130°C for reaction, and TLC monitored until the reaction was complete. The reaction system was cooled to room temperature, the reaction solution was slowly poured into a large amount of ice water, fully stirred, dissolved with ethyl acetate (30mL), extracted, and layered, the organic phase was washed successively with saturated aqueous sodium bicarbonate and saturated brine, and separated The organic phase was taken out, and the organic phase was dried with anhydrous magnesium sulfate. After filtration, the organic solvent was evaporated under reduced pressure, and the residue was separated and purified by column chromatography to obtain the title product, 0.35 g of white solid, and the yield was 64% (by N-(2 -Bromo-4-heptafluoroisopropyl-6-trifluoromethylphenyl)-2-fluoro-3-(N-methyl-benzamido)benzamide).
1H NMR(600MHz,CDCl 3,ppm):8.05(s,1H),7.86(s,1H),7.72(t,1H),7.33(br,2H),7.27 (br,2H),7.21(br,2H),7.14(t,1H),3.47(s,3H). 1 H NMR (600MHz, CDCl 3 , ppm): 8.05(s,1H),7.86(s,1H),7.72(t,1H),7.33(br,2H),7.27(br,2H),7.21(br ,2H),7.14(t,1H),3.47(s,3H).
实施例2：化合物I-46的制备Embodiment 2: the preparation of compound I-46
Figure PCTCN2022118920-appb-000019
Figure PCTCN2022118920-appb-000019
向反应瓶中加入甲苯(15mL)、N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-2-氟-3-(N-甲基-苯甲酰胺基)苯甲酰胺(0.53g，0.79mmol)、三溴氧磷(5.60g，19.14mmol)升温至100℃反应，TLC监测至反应完全。将反应体系降温至室温，将反应液缓慢倾入大量冰水中，充分搅拌，用乙酸乙酯(30mL)溶解、萃取、分层，有机相依次用饱和碳酸氢钠水溶液和饱和食盐水洗涤，分出有机相，将有机相用无水硫酸镁干燥，过滤后减压蒸出有机溶剂，残余物经柱色谱分离纯化得标题物(化合物I-46)，白色固体0.38g，收率为65％(以N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-2-氟-3-(N-甲基-苯甲酰胺基)苯甲酰胺计)。To the reaction flask was added toluene (15 mL), N-(2-bromo-4-heptafluoroisopropyl-6-trifluoromethylphenyl)-2-fluoro-3-(N-methyl-benzamide Base) benzamide (0.53g, 0.79mmol) and phosphorus oxybromide (5.60g, 19.14mmol) were heated to 100°C for reaction, and the reaction was monitored by TLC until the reaction was complete. The reaction system was cooled to room temperature, the reaction solution was slowly poured into a large amount of ice water, fully stirred, dissolved with ethyl acetate (30mL), extracted, and layered, the organic phase was washed successively with saturated aqueous sodium bicarbonate and saturated brine, and separated The organic phase was taken out, and the organic phase was dried with anhydrous magnesium sulfate. After filtration, the organic solvent was evaporated under reduced pressure. The residue was separated and purified by column chromatography to obtain the title compound (Compound I-46), a white solid of 0.38 g, and the yield was 65%. (as N-(2-bromo-4-heptafluoroisopropyl-6-trifluoromethylphenyl)-2-fluoro-3-(N-methyl-benzamido)benzamide).
1H NMR(600MHz,CDCl 3,ppm):8.06(s,1H),7.87(s,1H),7.65(t,1H),7.32(br,2H),7.26(br,2H),7.20(br,2H),7.14(t,1H),3.46(s,3H). 1 H NMR (600MHz, CDCl 3 , ppm): 8.06(s, 1H), 7.87(s, 1H), 7.65(t, 1H), 7.32(br, 2H), 7.26(br, 2H), 7.20(br ,2H),7.14(t,1H),3.46(s,3H).
实施例3：化合物I-122的制备Embodiment 3: the preparation of compound I-122
1)N-(2,6-二溴-4-七氟异丙基苯基)-2-氟-3-(N-甲基-2,2-二氟-1,3-苯并二噁茂-5-甲酰胺基)苯甲酰胺的制备1) N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluoro-3-(N-methyl-2,2-difluoro-1,3-benzodioxine Preparation of phenocene-5-carboxamido)benzamide
Figure PCTCN2022118920-appb-000020
Figure PCTCN2022118920-appb-000020
向反应瓶中加入3-(N-甲基-2,2-二氟-1,3-苯并二噁茂-5-甲酰胺基)-2-氟苯甲酸(1.07g，3.0mmol)、氯化亚砜(1.80g)、甲苯(10mL)和DMF(1滴)，升温至100℃反应4小时，减压蒸出氯化亚砜和甲苯，得到酰氯，白色固体，加入乙腈(15mL)、2,6-二溴-4-七氟异丙基苯胺(1.26g，2.90mmol)和碘化钾(0.09g，0.50mmol)，升温回流反应8小时。将反应体系冷却至室温，加入乙酸乙酯(30mL)，依次用饱和碳酸氢钠水溶液和饱和食盐水洗涤，用无水硫酸镁干燥，过滤，减压蒸出溶剂，残余物经柱色谱分离纯化得标题物，白色固体1.73g，收率为78％(以2,6-二溴-4-七氟异丙基苯胺计)。Add 3-(N-methyl-2,2-difluoro-1,3-benzodioxol-5-carboxamido)-2-fluorobenzoic acid (1.07g, 3.0mmol) to the reaction flask, Thionyl chloride (1.80g), toluene (10mL) and DMF (1 drop) were heated to 100°C for 4 hours, and the thionyl chloride and toluene were distilled off under reduced pressure to obtain the acid chloride as a white solid, and acetonitrile (15mL) was added , 2,6-dibromo-4-heptafluoroisopropylaniline (1.26g, 2.90mmol) and potassium iodide (0.09g, 0.50mmol), heated and refluxed for 8 hours. The reaction system was cooled to room temperature, ethyl acetate (30 mL) was added, washed successively with saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure, and the residue was separated and purified by column chromatography The title product was obtained, 1.73 g of white solid, with a yield of 78% (calculated as 2,6-dibromo-4-heptafluoroisopropylaniline).
1H NMR(600MHz,CDCl 3,ppm):8.09-8.04(m,2H),7.87(s,2H),7.47-7.43(m,1H),7.34-7.29(m,1H),7.20(s,1H),7.05(d,1H),6.89(d,1H),3.50(s,3H). 1 H NMR (600MHz, CDCl 3 , ppm): 8.09-8.04 (m, 2H), 7.87 (s, 2H), 7.47-7.43 (m, 1H), 7.34-7.29 (m, 1H), 7.20 (s, 1H), 7.05(d, 1H), 6.89(d, 1H), 3.50(s, 3H).
2)N-(2,6-二溴-4-七氟异丙基苯基)-3-(N-甲基-2,2-二氟-1,3-苯并二噁茂-5-甲酰胺基)-2-氟苯甲亚胺酰溴(化合物I-122)的制备2) N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-3-(N-methyl-2,2-difluoro-1,3-benzodioxol-5- Preparation of formamido)-2-fluorobenzimidoyl bromide (compound I-122)
Figure PCTCN2022118920-appb-000021
Figure PCTCN2022118920-appb-000021
向反应瓶中加入甲苯(5mL)、N-(2,6-二溴-4-七氟异丙基苯基)-2-氟-3-(N-甲基-2,2-二氟-1,3-苯并二噁茂-5-甲酰胺基)苯甲酰胺(0.76g，1.00mmol)、三溴氧磷(6.07g，20.70mmol)升温至100℃反应，TLC监测至反应完全。将反应体系降温至室温，将反应液缓慢倾入大量冰水中，充分搅拌，用乙酸乙酯(30mL)溶解、萃取、分层，有机相依次用饱和碳酸氢钠水 溶液和饱和食盐水洗涤，分出有机相，将有机相用无水硫酸镁干燥，过滤后减压蒸出有机溶剂，残余物经柱色谱分离纯化得标题物，白色固体0.58g，收率为70％(以N-(2,6-二溴-4-七氟异丙基苯基)-2-氟-3-(N-甲基-2,2-二氟-1,3-苯并二噁茂-5-甲酰胺基)苯甲酰胺计)Add toluene (5 mL), N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluoro-3-(N-methyl-2,2-difluoro- 1,3-Benzodioxol-5-carboxamido)benzamide (0.76g, 1.00mmol) and phosphorus oxybromide (6.07g, 20.70mmol) were heated to 100°C for reaction, and TLC monitored until the reaction was complete. The reaction system was cooled to room temperature, the reaction solution was slowly poured into a large amount of ice water, fully stirred, dissolved with ethyl acetate (30mL), extracted, and layered, the organic phase was washed successively with saturated aqueous sodium bicarbonate and saturated brine, and separated The organic phase was taken out, and the organic phase was dried with anhydrous magnesium sulfate. After filtration, the organic solvent was evaporated under reduced pressure, and the residue was separated and purified by column chromatography to obtain the title product, 0.58 g of white solid, and the yield was 70% (by N-(2 ,6-Dibromo-4-heptafluoroisopropylphenyl)-2-fluoro-3-(N-methyl-2,2-difluoro-1,3-benzodioxol-5-carboxamide base) benzamide
1H NMR(600MHz,CDCl 3,ppm):7.82(s,2H),7.75(t,1H),7.31(t,1H),7.21(t,1H),7.16(s,1H),7.04(d,1H),6.87(d,1H),3.46(s,3H). 1 H NMR (600MHz, CDCl 3 , ppm): 7.82(s, 2H), 7.75(t, 1H), 7.31(t, 1H), 7.21(t, 1H), 7.16(s, 1H), 7.04(d ,1H),6.87(d,1H),3.46(s,3H).
实施例4：化合物I-128的制备Embodiment 4: the preparation of compound I-128
1)N-(2-溴-6-二氟甲氧基-4-七氟异丙基苯基)-2-氟-3-(N-甲基-2,2-二氟-1,3-苯并二噁茂-5-甲酰胺基)苯甲酰胺的制备1) N-(2-bromo-6-difluoromethoxy-4-heptafluoroisopropylphenyl)-2-fluoro-3-(N-methyl-2,2-difluoro-1,3 -Preparation of benzodioxol-5-carboxamido)benzamide
Figure PCTCN2022118920-appb-000022
Figure PCTCN2022118920-appb-000022
向反应瓶中加入3-(N-甲基-2,2-二氟-1,3-苯并二噁茂-5-甲酰胺基)-2-氟苯甲酸(1.07g，3.0mmol)、氯化亚砜(1.80g)、甲苯(10mL)和DMF(1滴)，升温至100℃反应4小时，减压蒸出氯化亚砜和甲苯，得到酰氯，白色固体，加入乙腈(15mL)、2-溴-6-二氟甲氧基-4-七氟异丙基苯胺(1.19g，2.90mmol)和碘化钾(0.09g，0.50mmol)，升温回流反应8小时。将反应体系冷却至室温，加入乙酸乙酯(30mL)，依次用饱和碳酸氢钠水溶液和饱和食盐水洗涤，用无水硫酸镁干燥，过滤，减压蒸出溶剂，残余物经柱色谱分离纯化得标题物，白色固体1.76g，收率为81％(以2-溴-6-二氟甲氧基-4-七氟异丙基苯胺计)。Add 3-(N-methyl-2,2-difluoro-1,3-benzodioxol-5-carboxamido)-2-fluorobenzoic acid (1.07g, 3.0mmol) to the reaction flask, Thionyl chloride (1.80g), toluene (10mL) and DMF (1 drop) were heated to 100°C for 4 hours, and the thionyl chloride and toluene were distilled off under reduced pressure to obtain the acid chloride as a white solid, and acetonitrile (15mL) was added , 2-bromo-6-difluoromethoxy-4-heptafluoroisopropylaniline (1.19g, 2.90mmol) and potassium iodide (0.09g, 0.50mmol), heated and refluxed for 8 hours. The reaction system was cooled to room temperature, ethyl acetate (30 mL) was added, washed successively with saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure, and the residue was separated and purified by column chromatography The title product was obtained, 1.76 g of white solid, with a yield of 81% (calculated as 2-bromo-6-difluoromethoxy-4-heptafluoroisopropylaniline).
1H NMR(600MHz,CDCl 3,ppm):8.03(t,1H),7.96(d,1H),7.80(d,1H),7.50(s,1H),7.43(t,1H),7.31(t,1H),7.20(s,1H),7.05(br,1H),6.89(br,1H),6.55(t,1H),3.48(s,3H). 1 H NMR (600MHz, CDCl 3 , ppm): 8.03(t, 1H), 7.96(d, 1H), 7.80(d, 1H), 7.50(s, 1H), 7.43(t, 1H), 7.31(t ,1H),7.20(s,1H),7.05(br,1H),6.89(br,1H),6.55(t,1H),3.48(s,3H).
2)N-(2-溴-6-二氟甲氧基-4-七氟异丙基苯基)-3-(N-甲基-2,2-二氟-1,3-苯并二噁茂-5-甲酰胺基-2-氟苯甲亚胺酰溴(化合物I-128)的制备2) N-(2-bromo-6-difluoromethoxy-4-heptafluoroisopropylphenyl)-3-(N-methyl-2,2-difluoro-1,3-benzobis Preparation of oxol-5-carboxamido-2-fluorobenzimide bromide (compound I-128)
Figure PCTCN2022118920-appb-000023
Figure PCTCN2022118920-appb-000023
向反应瓶中加入甲苯(5mL)、N-(2-溴-6-二氟甲氧基-4-七氟异丙基苯基)-2-氟-3-(N-甲基-2,2-二氟-1,3-苯并二噁茂-5-甲酰胺基)苯甲酰胺(0.76g，1.00mmol)、三溴氧磷(6.07g，20.70mmol)升温至100℃反应，TLC监测至反应完全。将反应体系降温至室温，将反应液缓慢倾入大量冰水中，充分搅拌，用乙酸乙酯(30mL)溶解、萃取、分层，有机相依次用饱和碳酸氢钠水溶液和饱和食盐水洗涤，分出有机相，将有机相用无水硫酸镁干燥，过滤后减压蒸出有机溶剂，残余物经柱色谱分离纯化得标题物，白色固体0.57g，收率为70％(以N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-2-氟-3-(N-甲基-苯甲酰胺基)苯甲酰胺计)。Add toluene (5 mL), N-(2-bromo-6-difluoromethoxy-4-heptafluoroisopropylphenyl)-2-fluoro-3-(N-methyl-2, 2-Difluoro-1,3-benzodioxol-5-carboxamido)benzamide (0.76g, 1.00mmol), phosphorus oxybromide (6.07g, 20.70mmol) was heated to 100°C for reaction, TLC Monitor until the reaction is complete. The reaction system was cooled to room temperature, the reaction solution was slowly poured into a large amount of ice water, fully stirred, dissolved with ethyl acetate (30mL), extracted, and layered, the organic phase was washed successively with saturated aqueous sodium bicarbonate and saturated brine, and separated The organic phase was taken out, and the organic phase was dried with anhydrous magnesium sulfate. After filtration, the organic solvent was evaporated under reduced pressure, and the residue was separated and purified by column chromatography to obtain the title product, 0.57 g of white solid, and the yield was 70% (by N-(2 -Bromo-4-heptafluoroisopropyl-6-trifluoromethylphenyl)-2-fluoro-3-(N-methyl-benzamido)benzamide).
1H NMR(600MHz,CDCl 3,ppm):7.76(s,1H),7.72(t,1H),7.45(s,1H),7.31(t,1H),7.21(t,1H),7.15(s,1H),7.04(d,1H),6.87(d,1H),6.45(t,1H),3.46(s,3H). 1 H NMR (600MHz, CDCl 3 , ppm): 7.76(s, 1H), 7.72(t, 1H), 7.45(s, 1H), 7.31(t, 1H), 7.21(t, 1H), 7.15(s ,1H),7.04(d,1H),6.87(d,1H),6.45(t,1H),3.46(s,3H).
实施例5：化合物I-130的制备Embodiment 5: the preparation of compound I-130
Figure PCTCN2022118920-appb-000024
Figure PCTCN2022118920-appb-000024
向反应瓶中加入甲苯(5mL)、N-(2,6-二溴-4-七氟异丙基苯基)-2-氟-3-(N-甲基-2,2-二氟-1,3-苯并二噁茂-5-甲酰胺基)苯甲酰胺(0.76g，1.00mmol)、三氯氧磷(5ml)、DMF(0.10g)升温至130℃反应，TLC监测至反应完全。将反应体系降温至室温，将反应液缓慢倾入大量冰水中，充分搅拌，用乙酸乙酯(30mL)溶解、萃取、分层，有机相依次用饱和碳酸氢钠水溶液和饱和食盐水洗涤，分出有机相，将有机相用无水硫酸镁干燥，过滤后减压蒸出有机溶剂，残余物经柱色谱分离纯化得标题物，白色固体0.54g，收率为69％(以N-(2-溴-4-七氟异丙基-6-三氟甲基苯基)-2-氟-3-(N-甲基-苯甲酰胺基)苯甲酰胺计)。Add toluene (5 mL), N-(2,6-dibromo-4-heptafluoroisopropylphenyl)-2-fluoro-3-(N-methyl-2,2-difluoro- 1,3-Benzodioxol-5-carboxamido)benzamide (0.76g, 1.00mmol), phosphorus oxychloride (5ml), DMF (0.10g) was heated to 130°C for reaction, TLC monitored until the reaction completely. The reaction system was cooled to room temperature, the reaction solution was slowly poured into a large amount of ice water, fully stirred, dissolved with ethyl acetate (30mL), extracted, and layered, the organic phase was washed successively with saturated aqueous sodium bicarbonate and saturated brine, and separated The organic phase was taken out, and the organic phase was dried with anhydrous magnesium sulfate. After filtration, the organic solvent was evaporated under reduced pressure, and the residue was separated and purified by column chromatography to obtain the title product, 0.54 g of white solid, and the yield was 69% (by N-(2 -Bromo-4-heptafluoroisopropyl-6-trifluoromethylphenyl)-2-fluoro-3-(N-methyl-benzamido)benzamide).
1H NMR(600MHz,CDCl 3,ppm):7.83(t,1H),7.81(s,2H),7.33(t,1H),7.22(t,1H),7.17(s,1H),7.05(d,1H),6.88(d,1H),3.46(s,3H). 1 H NMR (600MHz, CDCl 3 , ppm): 7.83(t,1H),7.81(s,2H),7.33(t,1H),7.22(t,1H),7.17(s,1H),7.05(d ,1H),6.88(d,1H),3.46(s,3H).
实施例6：化合物I-176的制备Embodiment 6: the preparation of compound I-176
Figure PCTCN2022118920-appb-000025
Figure PCTCN2022118920-appb-000025
向反应瓶中加入四氢呋喃(5mL)、N-(2-溴-6-二氟甲氧基-4-七氟异丙基苯基)-3-(N-甲基-2,2-二氟-1,3-苯并二噁茂-5-甲酰胺基-2-氟苯甲亚胺酰溴(化合物I-128，150.0mg，0.19mmol)和甲硫醇钠(39.2mg，0.56mmol)，升温至50℃反应5小时。TLC监测至反应完全。将反应体系降温至室温，将反应液倾入大量水中，用乙酸乙酯萃取、分层，有机相依次用水和饱和食盐水洗涤，分出有机相，将有机相用无水硫酸镁干燥，过滤后减压蒸出有机溶剂，残余物经柱色谱分离纯化得标题物，白色固体102.0mg，收率为70％。Add tetrahydrofuran (5 mL), N-(2-bromo-6-difluoromethoxy-4-heptafluoroisopropylphenyl)-3-(N-methyl-2,2-difluoro -1,3-Benzodioxol-5-carboxamido-2-fluorobenzimide bromide (compound I-128, 150.0 mg, 0.19 mmol) and sodium methylthiolate (39.2 mg, 0.56 mmol) , heated up to 50°C and reacted for 5 hours. TLC monitored until the reaction was complete. The reaction system was cooled to room temperature, the reaction solution was poured into a large amount of water, extracted with ethyl acetate, and separated into layers. The organic phase was washed with water and saturated brine successively, and separated The organic phase was taken out, dried with anhydrous magnesium sulfate, filtered, and the organic solvent was distilled off under reduced pressure. The residue was separated and purified by column chromatography to obtain the title compound, 102.0 mg of white solid, with a yield of 70%.
1H NMR(600MHz,CDCl 3,ppm):7.64(s,1H),7.22(br,2H),7.03-6.94(m,4H),6.77(br,1H),6.34(t,1H),3.26(s,br,3H),2.57(s,br,3H). 1 H NMR (600MHz, CDCl 3 , ppm): 7.64(s,1H),7.22(br,2H),7.03-6.94(m,4H),6.77(br,1H),6.34(t,1H),3.26 (s,br,3H),2.57(s,br,3H).
实施例7：化合物I-618的制备Embodiment 7: the preparation of compound I-618
Figure PCTCN2022118920-appb-000026
Figure PCTCN2022118920-appb-000026
向反应瓶中加入四氢呋喃(3mL)、乙硫醇(11.6mg,0.37mmol)、氢化钠(60％，22.4mg，0.56mmol)，室温搅拌反应10分钟，将N-(2-溴-6-二氟甲氧基-4-七氟异丙基苯基)-3-(N-甲基-2,2-二氟-1,3-苯并二噁茂-5-甲酰胺基-2-氟苯甲亚胺酰溴(化合物I-128，150.0mg，0.19mmol)溶于四氢呋喃(2mL)，并将该溶液于室温加入到上述反应体系中搅拌反应2小时，TLC检测至反应完全。用1N盐酸将体系淬灭，加水稀释，用乙酸乙酯萃取、分层，有机相依次用水和饱和食盐水洗涤，分出有机相，将有机相用无水硫酸镁干燥，过滤后减压蒸出有机溶剂，残余物经柱色谱分离纯化得标题物，白色固体88.6mg，收率为59％。Add tetrahydrofuran (3mL), ethanethiol (11.6mg, 0.37mmol), sodium hydride (60%, 22.4mg, 0.56mmol) into the reaction flask, stir the reaction at room temperature for 10 minutes, and N-(2-bromo-6- Difluoromethoxy-4-heptafluoroisopropylphenyl)-3-(N-methyl-2,2-difluoro-1,3-benzodioxol-5-carboxamido-2- Fluorobenzimidoyl bromide (compound I-128, 150.0mg, 0.19mmol) was dissolved in tetrahydrofuran (2mL), and the solution was added to the above reaction system at room temperature and stirred for 2 hours, and TLC detected that the reaction was complete. Quench the system with 1N hydrochloric acid, dilute with water, extract with ethyl acetate, separate layers, wash the organic phase with water and saturated brine in turn, separate the organic phase, dry the organic phase with anhydrous magnesium sulfate, filter and evaporate under reduced pressure Organic solvent, the residue was separated and purified by column chromatography to obtain the title product, 88.6 mg of white solid, with a yield of 59%.
1H NMR(600MHz,CDCl 3,ppm):7.64(s,1H),7.21(br,2H),7.07(br,4H),6.77(br,1H),6.34(t,1H),3.26(br,5H),1.43(s,br,3H). 1 H NMR (600MHz, CDCl 3 , ppm): 7.64(s, 1H), 7.21(br, 2H), 7.07(br, 4H), 6.77(br, 1H), 6.34(t, 1H), 3.26(br ,5H),1.43(s,br,3H).
实施例8：化合物I-620的制备Embodiment 8: the preparation of compound I-620
Figure PCTCN2022118920-appb-000027
Figure PCTCN2022118920-appb-000027
向反应瓶中加入四氢呋喃(3mL)、1-1H-1,2,4-三氮唑(25.8mg,0.37mmol)、氢化钠(60％,22.4mg，0.56mmol),室温搅拌反应10分钟，将N-(2-溴-6-二氟甲氧基-4-七氟异丙基苯基)-3-(N-甲基-2,2-二氟-1,3-苯并二噁茂-5-甲酰胺基-2-氟苯甲亚胺酰溴(化合物I-128，150.0mg，0.19mmol)溶于四氢呋喃(2mL)，并将该溶液于室温加入到上述反应体系中，升温至50℃，搅拌反应5小时，TLC监测至反应完全。将体系降至室温，用1N盐酸淬灭，加水稀释，用乙 酸乙酯萃取、分层，有机相依次用水和饱和食盐水洗涤，分出有机相，将有机相用无水硫酸镁干燥，过滤后减压蒸出有机溶剂，残余物经柱色谱分离纯化得标题物，白色固体95.5mg，收率为63％。Add tetrahydrofuran (3mL), 1-1H-1,2,4-triazole (25.8mg, 0.37mmol), sodium hydride (60%, 22.4mg, 0.56mmol) into the reaction flask, and stir at room temperature for 10 minutes. N-(2-bromo-6-difluoromethoxy-4-heptafluoroisopropylphenyl)-3-(N-methyl-2,2-difluoro-1,3-benzodiox The bromide-5-carboxamido-2-fluorobenzimide bromide (compound I-128, 150.0mg, 0.19mmol) was dissolved in tetrahydrofuran (2mL), and the solution was added to the above reaction system at room temperature, and the temperature was raised to 50°C, stirred and reacted for 5 hours, and TLC monitored until the reaction was complete. The system was lowered to room temperature, quenched with 1N hydrochloric acid, diluted with water, extracted with ethyl acetate, separated into layers, and the organic phase was washed with water and saturated brine successively, and separated The organic phase was taken out, dried with anhydrous magnesium sulfate, filtered, and the organic solvent was distilled off under reduced pressure. The residue was separated and purified by column chromatography to obtain the title compound, 95.5 mg of white solid, with a yield of 63%.
1H NMR(600MHz,CDCl 3,ppm):9.13(s,1H),7.99(s,1H),7.67(s,1H),7.25(br,1H),7.17(br,1H),7.08-7.05(m,3H),7.00-6.97(m,1H),6.83(br,1H),6.34(t,1H),3.36(s,3H). 1 H NMR (600MHz, CDCl 3 , ppm): 9.13(s,1H),7.99(s,1H),7.67(s,1H),7.25(br,1H),7.17(br,1H),7.08-7.05 (m,3H),7.00-6.97(m,1H),6.83(br,1H),6.34(t,1H),3.36(s,3H).
实施例9：化合物I-626的制备Embodiment 9: the preparation of compound I-626
Figure PCTCN2022118920-appb-000028
Figure PCTCN2022118920-appb-000028
向反应瓶中加入四氢呋喃(5mL)、N-(2-溴-6-二氟甲氧基-4-七氟异丙基苯基)-3-(N-甲基-2,2-二氟-1,3-苯并二噁茂-5-甲酰胺基-2-氟苯甲亚胺酰溴(化合物I-128，150.0mg，0.19mmol)和乙醇钠(81.0mg，0.37mmol)，升温至50℃反应5小时。TLC监测至反应完全。将反应体系降温至室温，将反应液倾入大量水中，用乙酸乙酯萃取、分层，有机相依次用水和饱和食盐水洗涤，分出有机相，将有机相用无水硫酸镁干燥，过滤后减压蒸出有机溶剂，残余物经柱色谱分离纯化得标题物，白色固体71.0mg，收率为48％。Add tetrahydrofuran (5 mL), N-(2-bromo-6-difluoromethoxy-4-heptafluoroisopropylphenyl)-3-(N-methyl-2,2-difluoro -1,3-Benzodioxol-5-carboxamido-2-fluorobenzimide bromide (compound I-128, 150.0 mg, 0.19 mmol) and sodium ethoxide (81.0 mg, 0.37 mmol), warming React at 50°C for 5 hours. TLC monitors until the reaction is complete. The reaction system is cooled to room temperature, the reaction solution is poured into a large amount of water, extracted with ethyl acetate, layered, the organic phase is washed with water and saturated brine successively, and the organic phase is separated. phase, the organic phase was dried with anhydrous magnesium sulfate, filtered, and the organic solvent was distilled off under reduced pressure. The residue was separated and purified by column chromatography to obtain the title compound, 71.0 mg of white solid, with a yield of 48%.
1H NMR(600MHz,CDCl 3,ppm):7.61(br,1H),7.19(br,1H),7.05-7.02(m,2H),7.00-6.98(m,1H),6.94-6.92(m,1H),6.91-6.88(m,1H),6.76-6.75(m,1H),6.28(t,1H),4.51(br,2H),3.27(s,3H),1.47(t,3H). 1 H NMR (600MHz, CDCl 3 , ppm): 7.61(br,1H),7.19(br,1H),7.05-7.02(m,2H),7.00-6.98(m,1H),6.94-6.92(m, 1H),6.91-6.88(m,1H),6.76-6.75(m,1H),6.28(t,1H),4.51(br,2H),3.27(s,3H),1.47(t,3H).
实施例10：化合物I-628的制备Embodiment 10: the preparation of compound I-628
Figure PCTCN2022118920-appb-000029
Figure PCTCN2022118920-appb-000029
向反应瓶中加入四氢呋喃(5mL)、N-(2-溴-6-二氟甲氧基-4-七氟异丙基苯基)-3-(N-甲基-2,2-二氟-1,3-苯并二噁茂-5-甲酰胺基-2-氟苯甲亚胺酰溴(化合物I-128，150.0mg，0.19mmol)、甲胺盐酸盐(25.2mg，0.37mmol)和三乙胺(56.6mg，0.56mmol)。升温至50℃反应5小时。TLC检测至反应完毕。反应体系降至室温，倾入大量清水中，用乙酸乙酯萃取、分层，有机相依次用水和饱和食盐水洗涤，分出有机相，将有机相用无水硫酸镁干燥，过滤后减压蒸出有机溶剂，残余物经柱色谱分离纯化得标题物，白色固体122.3mg，收率为85％。Add tetrahydrofuran (5 mL), N-(2-bromo-6-difluoromethoxy-4-heptafluoroisopropylphenyl)-3-(N-methyl-2,2-difluoro -1,3-benzodioxol-5-carboxamido-2-fluorobenzimide bromide (compound I-128, 150.0mg, 0.19mmol), methylamine hydrochloride (25.2mg, 0.37mmol ) and triethylamine (56.6mg, 0.56mmol). Warm up to 50°C for 5 hours. TLC detects that the reaction is complete. The reaction system is lowered to room temperature, poured into a large amount of water, extracted with ethyl acetate, layered, organic phase Wash with water and saturated brine for several times, separate the organic phase, dry the organic phase with anhydrous magnesium sulfate, filter and distill off the organic solvent under reduced pressure, and the residue is separated and purified by column chromatography to obtain the title compound, white solid 122.3 mg, yield 85%.
1H NMR(600MHz,CDCl 3,ppm):7.57(br,1H),7.09-7.02(m,4H),6.92(br,2H),6.75(br,1H),6.31(t,1H),5.05(s,br,1H),3.27(s,3H),3.11(s,3H). 1 H NMR (600MHz, CDCl 3 , ppm): 7.57(br,1H),7.09-7.02(m,4H),6.92(br,2H),6.75(br,1H),6.31(t,1H),5.05 (s,br,1H),3.27(s,3H),3.11(s,3H).
实施例11：化合物I-630的制备Embodiment 11: the preparation of compound I-630
Figure PCTCN2022118920-appb-000030
Figure PCTCN2022118920-appb-000030
向反应瓶中加入四氢呋喃(5mL)、N-(2-溴-6-二氟甲氧基-4-七氟异丙基苯基)-3-(N-甲基-2,2-二氟-1,3-苯并二噁茂-5-甲酰胺基-2-氟苯甲亚胺酰溴(化合物I-128，150.0mg，0.19mmol)和4-乙基哌嗪(63.9mg，0.56mmol)，升温至50℃反应5小时。TLC监测至反应完全。将反应体系降温至室温，将反应液倾入大量水中，用乙酸乙酯萃取、分层，有机相依次用水和饱和食盐水洗涤，分出有机相，将有机相用无水硫酸镁干燥，过滤后减压蒸出有机溶剂，残余物经柱色谱分离纯化得标题物，白色固体120.7mg，收率为76％。Add tetrahydrofuran (5 mL), N-(2-bromo-6-difluoromethoxy-4-heptafluoroisopropylphenyl)-3-(N-methyl-2,2-difluoro -1,3-benzodioxol-5-carboxamido-2-fluorobenzimide bromide (compound I-128, 150.0mg, 0.19mmol) and 4-ethylpiperazine (63.9mg, 0.56 mmol), the temperature was raised to 50° C. for 5 hours. TLC was monitored to complete the reaction. The reaction system was cooled to room temperature, and the reaction solution was poured into a large amount of water, extracted with ethyl acetate, layered, and the organic phase was washed with water and saturated brine successively , separated the organic phase, dried the organic phase with anhydrous magnesium sulfate, filtered and evaporated the organic solvent under reduced pressure, and the residue was separated and purified by column chromatography to obtain the title compound, 120.7 mg of white solid, with a yield of 76%.
1H NMR(600MHz,CDCl 3,ppm):7.51(br,1H),7.06-6.83(m,7H),6.31(t,1H),3.90(br,2H),3.33(br,4H),2.66-2.44(m,6H),2.17(br,1H),1.10(t,3H). 1 H NMR (600MHz, CDCl 3 , ppm): 7.51(br,1H),7.06-6.83(m,7H),6.31(t,1H),3.90(br,2H),3.33(br,4H),2.66 -2.44(m,6H),2.17(br,1H),1.10(t,3H).
实施例12：化合物I-632的制备Embodiment 12: Preparation of Compound I-632
Figure PCTCN2022118920-appb-000031
Figure PCTCN2022118920-appb-000031
向反应瓶中加入四氢呋喃(3mL)、叔丁基硫醇(33.6mg，0.37mmol)、氢化钠(60％，22.4mg，0.56mmol)，室温搅拌反应10分钟，将N-(2-溴-6-二氟甲氧基-4-七氟异丙基苯基)-3-(N-甲基-2,2-二氟-1,3-苯并二噁茂-5-甲酰胺基-2-氟苯甲亚胺酰溴(化合物I-128，150.0mg，0.19mmol)溶于四氢呋喃(2mL)，并将该溶液于室温加入到上述反应体系中搅拌反应2小时，TLC检测至反应完全。用1N盐酸将体系淬灭，加水稀释，用乙酸乙酯萃取、分层，有机相依次用水和饱和食盐水洗涤，分出有机相，将有机相用无水硫酸镁干燥，过滤后减压蒸出有机溶剂，残余物经柱色谱分离纯化得标题物，白色固体136.8mg，收率为88％。Add tetrahydrofuran (3mL), tert-butyl mercaptan (33.6mg, 0.37mmol), sodium hydride (60%, 22.4mg, 0.56mmol) into the reaction flask, stir the reaction at room temperature for 10 minutes, and N-(2-bromo- 6-Difluoromethoxy-4-heptafluoroisopropylphenyl)-3-(N-methyl-2,2-difluoro-1,3-benzodioxol-5-carboxamido- 2-Fluorobenzimide bromide (compound I-128, 150.0mg, 0.19mmol) was dissolved in tetrahydrofuran (2mL), and the solution was added to the above reaction system at room temperature and stirred for 2 hours. TLC detected that the reaction was complete Quench the system with 1N hydrochloric acid, dilute with water, extract with ethyl acetate, separate layers, wash the organic phase with water and saturated brine in turn, separate the organic phase, dry the organic phase with anhydrous magnesium sulfate, filter and reduce pressure The organic solvent was distilled off, and the residue was separated and purified by column chromatography to obtain the title product, 136.8 mg of white solid, with a yield of 88%.
1H NMR(600MHz,CDCl 3,ppm):7.61(br,1H),7.12(br,2H),7.03(br,1H),6.90(br,3H),6.73(br,1H),6.25(t,1H),3.21(s,br,3H),1.66(s,9H). 1 H NMR (600MHz, CDCl 3 , ppm): 7.61(br,1H),7.12(br,2H),7.03(br,1H),6.90(br,3H),6.73(br,1H),6.25(t ,1H),3.21(s,br,3H),1.66(s,9H).
同时按照上述记载的方式还能够制备获得通式I所示的其它化合物。At the same time, other compounds represented by the general formula I can also be prepared according to the above-mentioned manner.
生物活性测定Bioactivity assay
实施例13杀虫活性测定Example 13 Determination of insecticidal activity
根据待测化合物的溶解性，用丙酮或二甲基亚砜溶解，然后用0.1％的吐温80溶液配制成所需浓度的待测液50毫升，丙酮或二甲基亚砜在总溶液中的含量不超过10％，待用。According to the solubility of the compound to be tested, dissolve it with acetone or dimethyl sulfoxide, and then use 0.1% Tween 80 solution to prepare 50 ml of the test solution of the required concentration, acetone or dimethyl sulfoxide in the total solution content of not more than 10%, for use.
实施例13.1对粘虫活性的测定Example 13.1 Determination of activity against armyworm
选新鲜玉米中部叶片剪成3厘米小段，放入至上述配制好的药液中浸渍10秒，阴干后置于放有滤纸的直径为9厘米的培养皿中，接入整齐的健康试虫(3龄)，每处理14头，试验设4次重复，设清水处理为空白对照。处理后放入24℃、相对湿度60％-70％、自然光照的室内培养，72小时后调查存活虫数，计算死亡率。Select fresh corn leaves in the middle and cut them into 3 cm segments, put them into the above-mentioned prepared medicinal solution and soak for 10 seconds, dry them in the shade, place them in a 9 cm diameter petri dish with filter paper, and insert neat healthy test insects ( 3 years old), 14 pigs were treated for each treatment, and the experiment was repeated 4 times, and the water treatment was set as the blank control. After treatment, put them into a room with 24°C, 60%-70% relative humidity, and natural light for indoor cultivation. After 72 hours, investigate the number of surviving insects and calculate the mortality rate.
部分供试的化合物中，化合物I-38、I-46、I-96、I-122、I-128、I-130、I-138、I-154、I-176、I-202、I-226、I-250、I-274、I-298、I-304、I-322、I-346、I-352、I-370、I-394、I-400、I-424、I-442、I-466、I-490、I-522、I-538、I-600、I-602、I-610、I-618、I-620、I-626、I-628、I-630、I-632、I-634、I-668、I-682和I-688在浓度为600mg/L时对粘虫的防效较好，死亡率均为100％。Among some tested compounds, compounds I-38, I-46, I-96, I-122, I-128, I-130, I-138, I-154, I-176, I-202, I- 226, I-250, I-274, I-298, I-304, I-322, I-346, I-352, I-370, I-394, I-400, I-424, I-442, I-466, I-490, I-522, I-538, I-600, I-602, I-610, I-618, I-620, I-626, I-628, I-630, I- When the concentration of 632, I-634, I-668, I-682 and I-688 is 600mg/L, the control effect on armyworm is better, and the mortality rate is 100%.
化合物I-38、I-46、I-96、I-122、I-128、I-130、I-138、I-154、I-176、I-202、I-226、I-250、I-274、I-298、I-304、I-322、I-346、I-352、I-370、I-394、I-400、I-424、I-442、I-466、I-490、I-522、I-538、I-600、I-602、I-610、I-618、I-620、I-626、I-628、I-630、I-632、I-634、I-668、I-682和I-688在浓度为100mg/L时对粘虫的防效较好，死亡率均为100％。Compounds I-38, I-46, I-96, I-122, I-128, I-130, I-138, I-154, I-176, I-202, I-226, I-250, I -274, I-298, I-304, I-322, I-346, I-352, I-370, I-394, I-400, I-424, I-442, I-466, I-490 , I-522, I-538, I-600, I-602, I-610, I-618, I-620, I-626, I-628, I-630, I-632, I-634, I When the concentration of -668, I-682 and I-688 is 100mg/L, the control effect on armyworm is better, and the mortality rate is 100%.
化合物I-38、I-46、I-96、I-122、I-128、I-130、I-138、I-154、I-176、I-202、I-226、I-250、I-274、I-298、I-304、I-322、I-346、I-352、I-370、I-394、I-400、I-424、I-442、I-466、I-490、I-522、I-538、I-600、I-602、I-610、I-618、I-620、I-626、I-628、I-630、I-632、I-634、I-668、I-682和I-688在浓度为10mg/L时对粘虫的防效较好，死亡率均为100％。Compounds I-38, I-46, I-96, I-122, I-128, I-130, I-138, I-154, I-176, I-202, I-226, I-250, I -274, I-298, I-304, I-322, I-346, I-352, I-370, I-394, I-400, I-424, I-442, I-466, I-490 , I-522, I-538, I-600, I-602, I-610, I-618, I-620, I-626, I-628, I-630, I-632, I-634, I When the concentration of -668, I-682 and I-688 is 10mg/L, the control effect on armyworm is better, and the mortality rate is 100%.
实施例13.2对小菜蛾活性的测定Example 13.2 Determination of Plutella xylostella activity
选室温培养的甘蓝叶片，除去表面蜡质层，用打孔器打成直径为2厘米的圆形叶碟，放入至配制好的药液中浸渍10秒，阴干后置于放有滤纸的直径为9厘米的培养皿中，接入整齐的健康试虫(2龄)，每处理10头，试验设4次重复，设清水处理为空白对照。处理后放入24℃、相对湿度60％-70％、自然光照的室内培养，72小时后调查存活虫数，计算死亡率。Select cabbage leaves cultivated at room temperature, remove the waxy layer on the surface, use a puncher to make a circular leaf disc with a diameter of 2 cm, put it into the prepared medicinal solution and soak it for 10 seconds, dry it in the shade, and place it in a container with filter paper. In a petri dish with a diameter of 9 cm, neat healthy test insects (2 instars) were inserted, and 10 insects were each treated. The test was repeated 4 times, and the water treatment was set as a blank control. After treatment, put them into a room with 24°C, 60%-70% relative humidity, and natural light for indoor cultivation. After 72 hours, investigate the number of surviving insects and calculate the mortality rate.
部分供试的化合物中，化合物I-38、I-46、I-96、I-122、I-128、I-130、I-138、I-154、I-176、I-202、I-226、I-250、I-274、I-298、I-304、I-322、I-346、I-352、I-370、I-394、I-400、I-424、I-442、I-466、I-490、I-522、I-538、I-600、I-602、I-610、I-618、I-620、I-626、I-628、I-630、I-632、I-634、I-668、I-682和I-688在浓度为600mg/L时对小菜蛾的防效较好，死亡率均为100％。Among some tested compounds, compounds I-38, I-46, I-96, I-122, I-128, I-130, I-138, I-154, I-176, I-202, I- 226, I-250, I-274, I-298, I-304, I-322, I-346, I-352, I-370, I-394, I-400, I-424, I-442, I-466, I-490, I-522, I-538, I-600, I-602, I-610, I-618, I-620, I-626, I-628, I-630, I- When the concentration of 632, I-634, I-668, I-682 and I-688 was 600mg/L, the control effect on Plutella xylostella was better, and the mortality rate was 100%.
化合物I-38、I-46、I-96、I-122、I-128、I-130、I-138、I-154、I-176、I-202、I-226、I-250、I-274、I-298、I-304、I-322、I-346、I-352、I-370、I-394、I-400、I-424、I-442、I-466、I-490、I-522、I-538、I-600、I-602、I-610、I-618、I-620、I-626、I-628、I-630、I-632、I-634、I-668、I-682和I-688在浓度为100mg/L时对小菜蛾的防效较好，死亡率均为100％。Compounds I-38, I-46, I-96, I-122, I-128, I-130, I-138, I-154, I-176, I-202, I-226, I-250, I -274, I-298, I-304, I-322, I-346, I-352, I-370, I-394, I-400, I-424, I-442, I-466, I-490 , I-522, I-538, I-600, I-602, I-610, I-618, I-620, I-626, I-628, I-630, I-632, I-634, I When the concentration of -668, I-682 and I-688 is 100mg/L, the control effect on Plutella xylostella is better, and the mortality rate is 100%.
化合物I-38、I-46、I-96、I-122、I-128、I-130、I-138、I-154、I-202、I-226、I-250、I-274、I-298、I-304、I-322、I-346、I-352、I-370、I-394、I-400、I-424、I-442、I-466、I-490、I-522、I-538、I-600、I-602、I-610、I-626、I-668、I-682和I-688在浓度为10mg/L时对小菜蛾的防效较好，死亡率均为100％。Compounds I-38, I-46, I-96, I-122, I-128, I-130, I-138, I-154, I-202, I-226, I-250, I-274, I -298, I-304, I-322, I-346, I-352, I-370, I-394, I-400, I-424, I-442, I-466, I-490, I-522 , I-538, I-600, I-602, I-610, I-626, I-668, I-682 and I-688 have better control effect on diamondback moth when the concentration is 10mg/L, and the mortality Both are 100%.
实施例13.3对桃蚜活性的测定Example 13.3 Determination of Peach Aphid Activity
取直径6厘米培养皿，皿底覆一层滤纸，并滴加适量自来水保湿。从培养桃蚜的甘蓝植株上剪取大小适宜(直径约3厘米)且长有15-30头蚜虫的甘蓝叶片，去除有翅蚜和叶片正面的蚜虫，调查结束后，叶背向置于培养皿内，用手持式Airbrush喷雾器进行喷雾处理，压力为10psi(约0.7kg/cm 2),喷液量为0.5毫升，试验设3次重复，处理后置于标准观察室内，48小时后调查存活数，计算死亡率。 Take a petri dish with a diameter of 6 cm, cover the bottom of the dish with a layer of filter paper, and add an appropriate amount of tap water to moisturize it. Cut the cabbage leaves with a suitable size (about 3 cm in diameter) and 15-30 aphids from the cabbage plants for cultivating peach aphids, and remove the winged aphids and the aphids on the front of the leaves. In the dish, spray treatment with a hand-held Airbrush sprayer, the pressure is 10psi (about 0.7kg/cm 2 ), the spray volume is 0.5ml, and the test is repeated 3 times. After treatment, it is placed in a standard observation room, and the survival is investigated after 48 hours. number to calculate the death rate.
部分供试的化合物中，化合物I-38、I-46、I-96、I-122、I-128、I-130、I-138、I-154、I-202、I-226、I-250、I-298、I-304、I-322、I-346、I-352、I-370、I-400、I-424、I-442、I-466、I-490、I-610、I-626、I-628、I-634、I-668、I-682和I-688在浓度为600mg/L时对桃蚜的防效较好，死亡率均为100％。Among some tested compounds, compounds I-38, I-46, I-96, I-122, I-128, I-130, I-138, I-154, I-202, I-226, I- 250, I-298, I-304, I-322, I-346, I-352, I-370, I-400, I-424, I-442, I-466, I-490, I-610, When the concentration of I-626, I-628, I-634, I-668, I-682 and I-688 was 600mg/L, the control effect on peach aphid was better, and the mortality rate was 100%.
实施例14杀螨活性测定Embodiment 14 Determination of acaricidal activity
根据待测化合物的溶解性，用丙酮或二甲基亚砜溶解，然后用0.1％的吐温80溶液配制成所需浓度的待测液50毫升，丙酮或二甲基亚砜在总溶液中的含量不超过10％。According to the solubility of the compound to be tested, dissolve it with acetone or dimethyl sulfoxide, and then use 0.1% Tween 80 solution to prepare 50 ml of the test solution of the required concentration, acetone or dimethyl sulfoxide in the total solution The content does not exceed 10%.
取两片真叶菜豆苗，接种朱砂叶螨成螨并调查基数后，用手持式Airbrush喷雾器进行整株喷雾处理，试验设3次重复，处理后置于标准观察室，72小时后调查存活螨数，计算死亡率。Take two pieces of true-leaf vegetable bean sprouts, inoculate them into adults of Tetranychus cinnabarinus and investigate the base number, then use a hand-held Airbrush sprayer to spray the whole plant. The experiment was repeated 3 times. After the treatment, they were placed in a standard observation room, and the number of surviving mites was investigated after 72 hours. Calculate the mortality rate.
部分供试的化合物中，化合物I-122、I-128、I-154、I-202、I-298、I-322、I-346、I-352、I-370、I-610、I-618、I-682和I-688在浓度为600mg/L时对朱砂叶螨成螨的防效较好，死亡率均为100％。Among some tested compounds, compounds I-122, I-128, I-154, I-202, I-298, I-322, I-346, I-352, I-370, I-610, I- When the concentration of 618, I-682 and I-688 is 600mg/L, the control effect on adult mites of Tetranychus cinnabarinus is better, and the mortality rate is 100%.
通过本发明上述记载的制备过程获得的通式I所示的其它化合物也具有上述相应的特性，达到意想不到的效果。Other compounds represented by the general formula I obtained through the above-mentioned preparation process of the present invention also have the above-mentioned corresponding characteristics and achieve unexpected effects.

Claims (7)

  1. 一种亚胺类化合物，其特征在于：亚胺类化合物结构如通式I所示：An imine compound is characterized in that: the structure of the imine compound is as shown in general formula I:
    Figure PCTCN2022118920-appb-100001
    Figure PCTCN2022118920-appb-100001
    式中：In the formula:
    Q选自
    Figure PCTCN2022118920-appb-100002
    Q from
    Figure PCTCN2022118920-appb-100002
    X 1选自卤素、硝基、氰基、CONH 2、CHO、C 1-C 6烷基、C 1-C 6卤代烷基、C 2-C 6烯基、C 2-C 6卤代烯基、C 2-C 6炔基、C 2-C 6卤代炔基、C 1-C 6烷氧基、C 1-C 6卤代烷氧基、C 1-C 6烷硫基、C 1-C 6卤代烷硫基、C 1-C 6烷基氨基、C 1-C 6二烷基氨基、C 1-C 6烷氧基羰基、C 1-C 6烷基羰基、C 1-C 6卤代烷基羰基、C 1-C 6烷基磺酰基、C 1-C 6卤代烷基磺酰基、C 1-C 6烷基亚磺酰基、C 1-C 6卤代烷基亚磺酰基、C 1-C 6烷基氨基羰基或C 1-C 6烷基氨基磺酰基； X 1 is selected from halogen, nitro, cyano, CONH 2 , CHO, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl , C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylamino, C 1 -C 6 dialkylamino, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkyl Carbonyl, C 1 -C 6 Alkylsulfonyl, C 1 -C 6 Haloalkylsulfonyl, C 1 -C 6 Alkylsulfinyl, C 1 -C 6 Haloalkylsulfinyl, C 1 -C 6 Alkane Aminocarbonyl or C 1 -C 6 alkylaminosulfonyl;
    m选自0、1、2、3、4或5；m is selected from 0, 1, 2, 3, 4 or 5;
    X 2和X 3可相同或不同的分别选自H、卤素、硝基、氰基、C 1-C 6烷基、C 1-C 6卤代烷基、C 2-C 6烯基、C 2-C 6卤代烯基、C 2-C 6炔基、C 2-C 6卤代炔基； X 2 and X 3 can be the same or different and are selected from H, halogen, nitro, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 - C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl;
    R 1选自H、C 1-C 6烷基、C 1-C 6卤代烷基或氰基亚甲基； R 1 is selected from H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or cyano methylene;
    R 2选自H、卤素、C 1-C 6烷基、C 1-C 6卤代烷基、C 2-C 6烯基、C 2-C 6卤代烯基、C 1-C 6烷基胺基、C 1-C 6卤代烷基胺基、C 1-C 6二烷基胺基、C 1-C 6卤代二烷基胺基、C 1-C 6烷氧基、C 1-C 6卤代烷氧基、C 2-C 6烯基氧基、C 2-C 6卤代烯基氧基、C 2-C 6炔基氧基、C 2-C 6卤代炔基氧基、C 1-C 6烷硫基、C 1-C 6卤代烷硫基、C 2-C 6烯基硫基、C 2-C 6卤代烯基硫基、C 2-C 6炔基硫基、C 2-C 6卤代炔基硫基、C 1-C 6烷氧基亚甲基、C 1-C 6卤代烷氧基亚甲基、C 1-C 6烷硫基亚甲基、C 1-C 6卤代烷硫基亚甲基、C 1-C 6烷胺基亚甲基、C 1-C 6卤代烷胺基亚甲基、C 1-C 6二烷胺基亚甲基、C 1-C 6卤代二烷胺基亚甲基、苯基、氨基、肼基、氰基、氰基亚甲基、1-吡咯烷基、1-哌啶基、4-吗啉基、1-1H-吡唑基、1-1H-咪唑基、1-1H-1,2,4-三氮唑基、2-2H-1,2,3-三氮唑基或4位被下述基团取代的哌嗪-1-基，其中下述基团为：C 1-C 6烷基、C 1-C 6烷基羰基或苯基； R 2 is selected from H, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkylamine C 1 -C 6 haloalkylamino group, C 1 -C 6 dialkylamino group, C 1 -C 6 halodialkylamino group, C 1 -C 6 alkoxy group , C 1 -C 6 Haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 2 -C 6 haloalkynyloxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 2 -C 6 alkenylthio, C 2 -C 6 haloalkenylthio, C 2 -C 6 alkynylthio, C 2 -C 6 haloalkynylthio, C 1 -C 6 alkoxymethylene, C 1 -C 6 haloalkoxymethylene, C 1 -C 6 alkylthiomethylene, C 1 -C 6 haloalkylthiomethylene, C 1 -C 6 alkylaminomethylene, C 1 -C 6 haloalkylaminomethylene, C 1 -C 6 dialkylaminomethylene, C 1 -C 6 Halodialkylaminomethylene, phenyl, amino, hydrazino, cyano, cyanomethylene, 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, 1-1H-pyridine Azolyl, 1-1H-imidazolyl, 1-1H-1,2,4-triazolyl, 2-2H-1,2,3-triazolyl, or piperine whose 4-position is substituted by the following groups Oxyzin-1-yl, wherein the following groups are: C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl or phenyl;
    Y 1和Y 2可相同或不同的选自卤素、C 1-C 6烷基、C 1-C 6卤代烷基、C 1-C 6烷氧基、C 1-C 6卤代烷氧基、C 1-C 6烷硫基或C 1-C 6卤代烷硫基。 Y 1 and Y 2 may be the same or different and are selected from halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio or C 1 -C 6 haloalkylthio.
  2. 按权利要求1所述的亚胺类化合物，其特征在于：所述通式I中：The imine compound according to claim 1, characterized in that: in the general formula I:
    Q选自
    Figure PCTCN2022118920-appb-100003
    Q from
    Figure PCTCN2022118920-appb-100003
    X 1选自卤素、硝基、氰基、CONH 2、CHO、C 1-C 3烷基、C 1-C 3卤代烷基、C 2-C 4烯基、C 2-C 4卤代烯基、C 2-C 4炔基、C 2-C 4卤代炔基、C 1-C 3烷氧基、C 1-C 3卤代烷氧基、C 1-C 3烷硫基、C 1-C 3卤代烷硫基、C 1-C 3烷基氨基、C 1-C 3二烷基氨基、C 1-C 3烷氧基羰基、C 1-C 3烷基羰基、C 1-C 3卤代烷基羰基、C 1-C 3烷基磺酰基、C 1-C 3卤代烷基磺酰基、C 1-C 3烷基亚磺酰基、C 1-C 3卤代烷基亚磺酰基、C 1-C 3烷基氨基羰基或C 1-C 3烷基氨基磺酰基； X 1 is selected from halogen, nitro, cyano, CONH 2 , CHO, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl , C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, C 1 -C 3 alkylamino, C 1 -C 3 dialkylamino, C 1 -C 3 alkoxycarbonyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkyl Carbonyl, C 1 -C 3 Alkylsulfonyl, C 1 -C 3 Haloalkylsulfonyl, C 1 -C 3 Alkylsulfinyl, C 1 -C 3 Haloalkylsulfinyl, C 1 -C 3 Alkane Aminocarbonyl or C 1 -C 3 alkylaminosulfonyl;
    m选自0、1、2、3、4或5；m is selected from 0, 1, 2, 3, 4 or 5;
    X 2和X 3可相同或不同的分别选自H、卤素、硝基、氰基、C 1-C 3烷基、C 1-C 3卤代烷基、C 2-C 4烯基、C 2-C 4卤代烯基、C 2-C 4炔基或C 2-C 4卤代炔基； X 2 and X 3 may be the same or different and are selected from H, halogen, nitro, cyano, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 4 alkenyl, C 2 - C 4 haloalkenyl, C 2 -C 4 alkynyl or C 2 -C 4 haloalkynyl;
    R 1选自H、C 1-C 3烷基、C 1-C 3卤代烷基或氰基亚甲基； R 1 is selected from H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or cyano methylene;
    R 2选自H、卤素、C 1-C 3烷基、C 1-C 3卤代烷基、C 2-C 4烯基、C 2-C 4卤代烯基、C 1-C 3烷基胺基、C 1-C 3卤代烷基胺基、C 1-C 3二烷基胺基、C 1-C 3卤代二烷基胺基、C 1-C 3烷氧基、C 1-C 3卤代烷基氧基、C 2-C 4烯基氧基、C 2-C 4卤代烯基氧基、C 2-C 4炔基氧基、C 2-C 4卤代炔基氧基、C 1-C 3烷硫基、C 1-C 3卤代烷硫基、C 2-C 4烯基硫基、C 2-C 4卤代烯基硫基、C 2-C 4炔基硫基、C 2-C 4卤代炔基硫基、C 1-C 3烷氧基亚甲基、C 1-C 3卤代烷氧基亚甲基、C 1-C 3烷硫基亚甲基、C 1-C 3卤代烷硫基亚甲基、C 1-C 3烷胺基亚甲基、C 1-C 3卤代烷胺基亚甲基、C 1-C 3二烷胺基亚甲基、C 1-C 3卤代二烷胺基亚甲基、苯基、氨基、肼基、氰基、氰基亚甲基、1-吡咯烷基、1-哌啶基、4-吗啉基、1-1H-吡唑基、1-1H-咪唑基、1-1H-1,2,4-三氮唑基或2-2H-1,2,3-三氮唑基或4位被下述基团取代的哌嗪-1-基，其中下述基团为：C 1-C 3烷基、C 1-C 3烷基羰基或苯基； R 2 is selected from H, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 1 -C 3 alkylamine C 1 -C 3 haloalkylamino, C 1 -C 3 dialkylamino, C 1 -C 3 halodialkylamino, C 1 -C 3 alkoxy , C 1 -C 3 Haloalkyloxy, C 2 -C 4 alkenyloxy, C 2 -C 4 haloalkenyloxy, C 2 -C 4 alkynyloxy, C 2 -C 4 haloalkynyloxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, C 2 -C 4 alkenylthio, C 2 -C 4 haloalkenylthio, C 2 -C 4 alkynylthio, C 2 -C 4 haloalkynylthio, C 1 -C 3 alkoxymethylene, C 1 -C 3 haloalkoxymethylene, C 1 -C 3 alkylthiomethylene, C 1 - C 3 haloalkylthiomethylene, C 1 -C 3 alkylaminomethylene, C 1 -C 3 haloalkylaminomethylene, C 1 -C 3 dialkylaminomethylene, C 1 -C 3 Halodialkylaminomethylene, phenyl, amino, hydrazino, cyano, cyanomethylene, 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, 1-1H- Pyrazolyl, 1-1H-imidazolyl, 1-1H-1,2,4-triazolyl or 2-2H-1,2,3-triazolyl or 4-position substituted by the following groups Piperazin-1-yl, wherein the following groups are: C 1 -C 3 alkyl, C 1 -C 3 alkylcarbonyl or phenyl;
    Y 1和Y 2可相同或不同的选自卤素、C 1-C 3烷基、C 1-C 3卤代烷基、C 1-C 3烷氧基、C 1-C 3卤代烷氧基、C 1-C 3烷硫基或C 1-C 3卤代烷硫基。 Y 1 and Y 2 may be the same or different and are selected from halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio or C 1 -C 3 haloalkylthio.
  3. 按权利要求2所述的亚胺类化合物，其特征在于：所述通式I中：The imine compound according to claim 2, characterized in that: in the general formula I:
    Q选自
    Figure PCTCN2022118920-appb-100004
    Q from
    Figure PCTCN2022118920-appb-100004
    X 1选自卤素、硝基、氰基、C 1-C 3卤代烷基、C 1-C 3烷氧基、C 1-C 3卤代烷氧基或C 1-C 3卤代烷硫基； X 1 is selected from halogen, nitro, cyano, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy or C 1 -C 3 haloalkylthio;
    m选自0、1、2或3；m is selected from 0, 1, 2 or 3;
    X 2和X 3可相同或不同的分别选自H或卤素； X 2 and X 3 can be the same or different and are independently selected from H or halogen;
    R 1选自H或C 1-C 3烷基； R 1 is selected from H or C 1 -C 3 alkyl;
    R 2选自卤素、C 1-C 3烷基胺基、C 1-C 3烷氧基、C 1-C 3烷硫基、1-1H-1,2,4-三氮唑基或4位被下述基团取代的哌嗪-1-基，其中下述基团为：C 1-C 3烷基、C 1-C 3烷基羰基或苯基； R 2 is selected from halogen, C 1 -C 3 alkylamino, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, 1-1H-1,2,4-triazolyl or 4 Piperazin-1-yl substituted by the following groups, wherein the following groups are: C 1 -C 3 alkyl, C 1 -C 3 alkylcarbonyl or phenyl;
    Y 1和Y 2可相同或不同的选自卤素、C 1-C 3卤代烷基或C 1-C 3卤代烷氧基。 Y 1 and Y 2 may be the same or different and are selected from halogen, C 1 -C 3 haloalkyl or C 1 -C 3 haloalkoxy.
  4. 按权利要求3所述的亚胺类化合物，其特征在于：所述通式I中：The imine compound according to claim 3, characterized in that: in the general formula I:
    Q选自
    Figure PCTCN2022118920-appb-100005
    Q from
    Figure PCTCN2022118920-appb-100005
    X 1选自F、Cl、Br、I、硝基、氰基、三氟甲基、甲氧基、二氟甲氧基、三氟甲氧基或三氟甲硫基； X is selected from F, Cl, Br, I, nitro, cyano, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy or trifluoromethylthio;
    m选自0、1或2；m is selected from 0, 1 or 2;
    X 2和X 3均选自F； Both X2 and X3 are selected from F;
    R 1选自H或甲基； R is selected from H or methyl;
    R 2选自F、Cl、Br、I、甲胺基、乙胺基、丙胺基、环丙烷基胺基、甲氧基、乙氧基、丙氧基、甲硫基、乙硫基、丙硫基、1-1H-1,2,4-三氮唑基、4-甲基哌嗪-1-基、4-乙基哌嗪-1-基、4-乙酰基哌嗪-1-基或4-苯基哌嗪-1-基； R is selected from F, Cl, Br, I, methylamino, ethylamino, propylamino, cyclopropanylamino, methoxy, ethoxy, propoxy, methylthio, ethylthio, propyl Thio, 1-1H-1,2,4-triazolyl, 4-methylpiperazin-1-yl, 4-ethylpiperazin-1-yl, 4-acetylpiperazin-1-yl or 4-phenylpiperazin-1-yl;
    Y 1和Y 2可相同或不同的选自F、Cl、Br、I、三氟甲基、三氟甲氧基或二氟甲氧基。 Y1 and Y2 may be the same or different and are selected from F, Cl, Br, I, trifluoromethyl, trifluoromethoxy or difluoromethoxy.
  5. 按权利要求4所述的亚胺类化合物，其特征在于：所述通式I中：The imine compound according to claim 4, characterized in that: in the general formula I:
    Q选自
    Figure PCTCN2022118920-appb-100006
    Q from
    Figure PCTCN2022118920-appb-100006
    X 1选自F、Cl、硝基、氰基、三氟甲基、甲氧基、二氟甲氧基、三氟甲氧基或三氟甲硫基； X is selected from F, Cl, nitro, cyano, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy or trifluoromethylthio;
    m选自0、1或2；m is selected from 0, 1 or 2;
    X 2和X 3均选自F； Both X2 and X3 are selected from F;
    R 1选自甲基； R 1 is selected from methyl;
    R 2选自Cl、Br、甲胺基、乙氧基、甲硫基、乙硫基、1-1H-1,2,4-三氮唑基或4-乙基哌嗪-1-基； R is selected from Cl, Br, methylamino, ethoxy, methylthio, ethylthio, 1-1H-1,2,4-triazolyl or 4-ethylpiperazin-1-yl;
    Y 1和Y 2可相同或不同的选自Br、三氟甲基或二氟甲氧基。 Y 1 and Y 2 may be the same or different and are selected from Br, trifluoromethyl or difluoromethoxy.
  6. 一种按照权利要求1-5任意一项所述的亚胺类化合物的应用，其特征在于：所述通式I所示化合物在农业、林业或卫生领域用作杀虫剂、杀螨剂的用途。A kind of application according to the imine compound described in any one of claim 1-5, it is characterized in that: the compound shown in described general formula I is used as insecticide, acaricide in agriculture, forestry or sanitation field use.
  7. 一种控制害虫或害螨的方法，其特征在于：将权利要求1所述的化合物以每公顷10克到1000克的有效剂量施于需要控制的害虫或害螨上，或其生长的介质上。A method for controlling pests or pests, characterized in that: applying the compound according to claim 1 to the pests or pests to be controlled, or the growth medium thereof, at an effective dose of 10 grams to 1000 grams per hectare .
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