WO2023051261A1 - 一种亚胺类化合物及其应用 - Google Patents
一种亚胺类化合物及其应用 Download PDFInfo
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- 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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- Prior art keywords
- sch
- alkyl
- haloalkyl
- phenyl
- halogen
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- 150000002466 imines Chemical class 0.000 title claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 88
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- 239000002917 insecticide Substances 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 747
- -1 cyano methylene Chemical group 0.000 claims description 360
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 67
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 32
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 13
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 8
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 7
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 7
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- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 7
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 5
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 4
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 4
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- 125000006767 (C2-C6) haloalkynyloxy group Chemical group 0.000 claims description 3
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- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
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- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- MXXWOMGUGJBKIW-YPCIICBESA-N piperine Chemical compound C=1C=C2OCOC2=CC=1/C=C/C=C/C(=O)N1CCCCC1 MXXWOMGUGJBKIW-YPCIICBESA-N 0.000 claims description 2
- 229940075559 piperine Drugs 0.000 claims description 2
- WVWHRXVVAYXKDE-UHFFFAOYSA-N piperine Natural products O=C(C=CC=Cc1ccc2OCOc2c1)C3CCCCN3 WVWHRXVVAYXKDE-UHFFFAOYSA-N 0.000 claims description 2
- 235000019100 piperine Nutrition 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
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- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 27
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- 238000004440 column chromatography Methods 0.000 description 18
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
- 239000003960 organic solvent Substances 0.000 description 14
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- KFCHYDKJTWTUOP-UHFFFAOYSA-N 3-[(2,2-difluoro-1,3-benzodioxole-5-carbonyl)-methylamino]-2-fluorobenzoic acid Chemical compound N(C1=C(F)C(C(=O)O)=CC=C1)(C(=O)C1=CC=2OC(OC=2C=C1)(F)F)C KFCHYDKJTWTUOP-UHFFFAOYSA-N 0.000 description 2
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- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical group CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- 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
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Abstract
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。结构如通式I所示，式中各取代基定义见说明书。通式I化合物具有优异的杀虫和杀螨活性，可用于防治各种害虫或害螨。
Description
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。
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。
WO2005073165A1和WO2010018714A1公开了具有杀虫活性的双酰胺结构类型化合物。
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。
发明内容
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。
为实现上述目的，本发明的技术方案如下：
一种亚胺类化合物：亚胺类化合物结构如通式I所示：
式中：
Q选自
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；
m选自0、1、2、3、4或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；
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
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；
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。
优选，所述通式I中：
Q选自
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；
m选自0、1、2、3、4或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；
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
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；
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。
进一步优选，所述通式I中：
Q选自
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；
m选自0、1、2或3；
X
2和X
3可相同或不同的分别选自H或卤素；
R
1选自H或C
1-C
3烷基；
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；
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。
再进一步优选，所述通式I中：
Q选自
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；
m选自0、1或2；
X
2和X
3均选自F；
R
1选自H或甲基；
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；
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。
更进一步优选，所述通式I中：
Q选自
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；
m选自0、1或2；
X
2和X
3均选自F；
R
1选自甲基；
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；
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。
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。
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)
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。
方法二(R
2为卤素)
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。
方法三(R
2为卤素)
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。
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)
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。
上述制备方法中所涉及的原料及中间体来源如下：
中间体V、中间体V-1和中间体X可以按US8853440B2方法制备。
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。
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：
卤素：指氟、氯、溴或碘。
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。
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。
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。
卤代烯基：可被卤原子取代至少一个或多个氢原子的烯基。
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。
卤代炔基：可被卤原子取代至少一个或多个氢原子的炔基。
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。
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。
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。
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。
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。
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。
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。
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。
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。
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。
烷氧基羰基：烷基-O-CO-，例如CH
3OCO-。
烷基羰基：烷基-CO-，例如CH
3CO-
烷基磺酰基：烷基-S(O)
2-，例如甲基磺酰基。
烷基亚磺酰基：烷基-S(O)-，例如甲基亚磺酰基。
烷基氨基羰基：烷基-NH-CO-，例如CH
3NHCO-。
烷基氨基磺酰基：烷基-NH-S(O)
2-，例如CH
3NH S(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。
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。
表1
I
| 编号 | Q | R 1 | R 2 | Y 1 | Y 2 |
| I-1 | phenyl | CH 3 | CH 3 | I | I |
| I-2 | phenyl | CH 3 | CH 3 | Br | Br |
| I-3 | phenyl | CH 3 | CH 3 | Cl | Cl |
| I-4 | phenyl | CH 3 | CH 3 | F | F |
| I-5 | phenyl | CH 3 | CH 3 | Br | CH 3 |
| I-6 | phenyl | CH 3 | CH 3 | Br | CF 3 |
| I-7 | phenyl | CH 3 | CH 3 | Br | OCF 3 |
| I-8 | phenyl | CH 3 | CH 3 | Br | OCHF 2 |
| I-9 | phenyl | CH 3 | H | I | I |
| I-10 | phenyl | CH 3 | H | Br | Br |
| I-11 | phenyl | CH 3 | H | Cl | Cl |
| I-12 | phenyl | CH 3 | H | F | F |
| I-13 | phenyl | CH 3 | H | Br | CH 3 |
| I-14 | phenyl | CH 3 | H | Br | CF 3 |
| I-15 | phenyl | CH 3 | H | Br | OCF 3 |
| I-16 | phenyl | CH 3 | H | Br | OCHF 2 |
| I-17 | phenyl | H | CH 3 | I | I |
| I-18 | phenyl | H | CH 3 | Br | Br |
| I-19 | phenyl | H | CH 3 | Cl | Cl |
| I-20 | phenyl | H | CH 3 | F | F |
| I-21 | phenyl | H | CH 3 | Br | CH 3 |
| I-22 | phenyl | H | CH 3 | Br | CF 3 |
| I-23 | phenyl | H | CH 3 | Br | OCF 3 |
| I-24 | phenyl | H | CH 3 | Br | OCHF 2 |
| I-25 | phenyl | H | H | I | I |
| I-26 | phenyl | H | H | Br | Br |
| I-27 | phenyl | H | H | Cl | Cl |
| I-28 | phenyl | H | H | F | F |
| I-29 | phenyl | H | H | Br | CH 3 |
| I-30 | phenyl | H | H | Br | CF 3 |
| I-31 | phenyl | H | H | Br | OCF 3 |
| I-32 | phenyl | H | H | Br | OCHF 2 |
| I-33 | phenyl | CH 3 | Cl | I | I |
| I-34 | phenyl | CH 3 | Cl | Br | Br |
| I-35 | phenyl | CH 3 | Cl | Cl | Cl |
| I-36 | phenyl | CH 3 | Cl | F | F |
| I-37 | phenyl | CH 3 | Cl | Br | CH 3 |
| I-38 | phenyl | CH 3 | Cl | Br | CF 3 |
| I-39 | phenyl | CH 3 | Cl | Br | OCF 3 |
| I-40 | phenyl | CH 3 | Cl | Br | OCHF 2 |
| I-41 | phenyl | CH 3 | Br | I | I |
| I-42 | phenyl | CH 3 | Br | Br | Br |
| I-43 | phenyl | CH 3 | Br | Cl | Cl |
| I-44 | phenyl | CH 3 | Br | F | F |
| I-45 | phenyl | CH 3 | Br | Br | CH 3 |
| I-46 | phenyl | CH 3 | Br | Br | CF 3 |
| I-47 | phenyl | CH 3 | Br | Br | OCF 3 |
| I-48 | phenyl | CH 3 | Br | Br | OCHF 2 |
| I-49 | phenyl | CH 3 | SCH 3 | I | I |
| I-50 | phenyl | CH 3 | SCH 3 | Br | Br |
| I-51 | phenyl | CH 3 | SCH 3 | Cl | Cl |
| I-52 | phenyl | CH 3 | SCH 3 | F | F |
| I-53 | phenyl | CH 3 | SCH 3 | Br | CH 3 |
| I-54 | phenyl | CH 3 | SCH 3 | Br | CF 3 |
| I-55 | phenyl | CH 3 | SCH 3 | Br | OCF 3 |
| I-56 | phenyl | CH 3 | SCH 3 | Br | OCHF 2 |
| I-57 | phenyl | cyclopropylmethyl | Br | I | I |
| I-58 | phenyl | cyclopropylmethyl | Br | Br | Br |
| I-59 | phenyl | cyclopropylmethyl | Br | Cl | Cl |
| I-60 | phenyl | cyclopropylmethyl | Br | F | F |
| I-61 | phenyl | cyclopropylmethyl | Br | Br | CH 3 |
| I-62 | phenyl | cyclopropylmethyl | Br | Br | CF 3 |
| I-63 | phenyl | cyclopropylmethyl | Br | Br | OCF 3 |
| I-64 | phenyl | cyclopropylmethyl | Br | Br | OCHF 2 |
| I-65 | phenyl | cyclopropylmethyl | Cl | I | I |
| I-66 | phenyl | cyclopropylmethyl | Cl | Br | Br |
| I-67 | phenyl | cyclopropylmethyl | Cl | Cl | Cl |
| I-68 | phenyl | cyclopropylmethyl | Cl | F | F |
| I-69 | phenyl | cyclopropylmethyl | Cl | Br | CH 3 |
| I-70 | phenyl | cyclopropylmethyl | Cl | Br | CF 3 |
| I-71 | phenyl | cyclopropylmethyl | Cl | Br | OCF 3 |
| I-72 | phenyl | cyclopropylmethyl | Cl | Br | OCHF 2 |
| I-73 | 4-fluorophenyl | cyclopropylmethyl | Br | I | I |
| I-74 | 4-fluorophenyl | cyclopropylmethyl | Br | Br | Br |
| I-75 | 4-fluorophenyl | cyclopropylmethyl | Br | Cl | Cl |
| I-76 | 4-fluorophenyl | cyclopropylmethyl | Br | F | F |
| I-77 | 4-fluorophenyl | cyclopropylmethyl | Br | Br | CH 3 |
| I-78 | 4-fluorophenyl | cyclopropylmethyl | Br | Br | CF 3 |
| I-79 | 4-fluorophenyl | cyclopropylmethyl | Br | Br | OCF 3 |
| I-80 | 4-fluorophenyl | cyclopropylmethyl | Br | Br | OCHF 2 |
| I-81 | 4-fluorophenyl | cyclopropylmethyl | Cl | I | I |
| I-82 | 4-fluorophenyl | cyclopropylmethyl | Cl | Br | Br |
| I-83 | 4-fluorophenyl | cyclopropylmethyl | Cl | Cl | Cl |
| I-84 | 4-fluorophenyl | cyclopropylmethyl | Cl | F | F |
| I-85 | 4-fluorophenyl | cyclopropylmethyl | Cl | Br | CH 3 |
| I-86 | 4-fluorophenyl | cyclopropylmethyl | Cl | Br | CF 3 |
| I-87 | 4-fluorophenyl | cyclopropylmethyl | Cl | Br | OCF 3 |
| I-88 | 4-fluorophenyl | cyclopropylmethyl | Cl | Br | OCHF 2 |
| I-89 | 4-fluorophenyl | CH 3 | Br | I | I |
| I-90 | 4-fluorophenyl | CH 3 | Br | Br | Br |
| I-91 | 4-fluorophenyl | CH 3 | Br | Cl | Cl |
| I-92 | 4-fluorophenyl | CH 3 | Br | F | F |
| I-93 | 4-fluorophenyl | CH 3 | Br | Br | CH 3 |
| I-94 | 4-fluorophenyl | CH 3 | Br | Br | CF 3 |
| I-95 | 4-fluorophenyl | CH 3 | Br | Br | OCF 3 |
| I-96 | 4-fluorophenyl | CH 3 | Br | Br | OCHF 2 |
| I-97 | 4-fluorophenyl | CH 3 | Cl | I | I |
| I-98 | 4-fluorophenyl | CH 3 | Cl | Br | Br |
| I-99 | 4-fluorophenyl | CH 3 | Cl | Cl | Cl |
| I-100 | 4-fluorophenyl | CH 3 | Cl | F | F |
| I-101 | 4-fluorophenyl | CH 3 | Cl | Br | CH 3 |
| I-102 | 4-fluorophenyl | CH 3 | Cl | Br | CF 3 |
| I-103 | 4-fluorophenyl | CH 3 | Cl | Br | OCF 3 |
| I-104 | 4-fluorophenyl | CH 3 | Cl | Br | OCHF 2 |
| I-105 | benzo[d][1,3]dioxol-5-yl | CH 3 | Br | I | I |
| I-106 | benzo[d][1,3]dioxol-5-yl | CH 3 | Br | Br | Br |
| I-107 | benzo[d][1,3]dioxol-5-yl | CH 3 | Br | Cl | Cl |
| I-108 | benzo[d][1,3]dioxol-5-yl | CH 3 | Br | F | F |
| I-109 | benzo[d][1,3]dioxol-5-yl | CH 3 | Br | Br | CH 3 |
| I-110 | benzo[d][1,3]dioxol-5-yl | CH 3 | Br | Br | CF 3 |
| I-111 | benzo[d][1,3]dioxol-5-yl | CH 3 | Br | Br | OCF 3 |
| I-112 | benzo[d][1,3]dioxol-5-yl | CH 3 | Br | Br | OCHF 2 |
| I-113 | benzo[d][1,3]dioxol-5-yl | CH 3 | Cl | I | I |
| I-114 | benzo[d][1,3]dioxol-5-yl | CH 3 | Cl | Br | Br |
| I-115 | benzo[d][1,3]dioxol-5-yl | CH 3 | Cl | Cl | Cl |
| I-116 | benzo[d][1,3]dioxol-5-yl | CH 3 | Cl | F | F |
| I-117 | benzo[d][1,3]dioxol-5-yl | CH 3 | Cl | Br | CH 3 |
| I-118 | benzo[d][1,3]dioxol-5-yl | CH 3 | Cl | Br | CF 3 |
| I-119 | benzo[d][1,3]dioxol-5-yl | CH 3 | Cl | Br | OCF 3 |
| I-120 | benzo[d][1,3]dioxol-5-yl | CH 3 | Cl | Br | OCHF 2 |
| I-121 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | Br | I | I |
| I-122 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | Br | Br | Br |
| I-123 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | Br | Cl | Cl |
| I-124 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | Br | F | F |
| I-125 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | Br | Br | CH 3 |
| I-126 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | Br | Br | CF 3 |
| I-127 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | Br | Br | OCF 3 |
| I-128 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | Br | Br | OCHF 2 |
| I-129 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | Cl | I | I |
| I-130 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | Cl | Br | Br |
| I-131 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | Cl | Cl | Cl |
| I-132 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | Cl | F | F |
| I-133 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | Cl | Br | CH 3 |
| I-134 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | Cl | Br | CF 3 |
| I-135 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | Cl | Br | OCF 3 |
| I-136 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | Cl | Br | OCHF 2 |
| I-137 | 3-fluorophenyl | CH 3 | Br | I | I |
| I-138 | 3-fluorophenyl | CH 3 | Br | Br | Br |
| I-139 | 3-fluorophenyl | CH 3 | Br | Cl | Cl |
| I-140 | 3-fluorophenyl | CH 3 | Br | F | F |
| I-141 | 3-fluorophenyl | CH 3 | Br | Br | CH 3 |
| I-142 | 3-fluorophenyl | CH 3 | Br | Br | CF 3 |
| I-143 | 3-fluorophenyl | CH 3 | Br | Br | OCF 3 |
| I-144 | 3-fluorophenyl | CH 3 | Br | Br | OCHF 2 |
| I-145 | 3-fluorophenyl | CH 3 | Cl | I | I |
| I-146 | 3-fluorophenyl | CH 3 | Cl | Br | Br |
| I-147 | 3-fluorophenyl | CH 3 | Cl | Cl | Cl |
| I-148 | 3-fluorophenyl | CH 3 | Cl | F | F |
| I-149 | 3-fluorophenyl | CH 3 | Cl | Br | CH 3 |
| I-150 | 3-fluorophenyl | CH 3 | Cl | Br | CF 3 |
| I-151 | 3-fluorophenyl | CH 3 | Cl | Br | OCF 3 |
| I-152 | 3-fluorophenyl | CH 3 | Cl | Br | OCHF 2 |
| I-153 | 3,4-difluorophenyl | CH 3 | Br | I | I |
| I-154 | 3,4-difluorophenyl | CH 3 | Br | Br | Br |
| I-155 | 3,4-difluorophenyl | CH 3 | Br | Cl | Cl |
| I-156 | 3,4-difluorophenyl | CH 3 | Br | F | F |
| I-157 | 3,4-difluorophenyl | CH 3 | Br | Br | CH 3 |
| I-158 | 3,4-difluorophenyl | CH 3 | Br | Br | CF 3 |
| I-159 | 3,4-difluorophenyl | CH 3 | Br | Br | OCF 3 |
| I-160 | 3,4-difluorophenyl | CH 3 | Br | Br | OCHF 2 |
| I-161 | 3,4-difluorophenyl | CH 3 | Cl | I | I |
| I-162 | 3,4-difluorophenyl | CH 3 | Cl | Br | Br |
| I-163 | 3,4-difluorophenyl | CH 3 | Cl | Cl | Cl |
| I-164 | 3,4-difluorophenyl | CH 3 | Cl | F | F |
| I-165 | 3,4-difluorophenyl | CH 3 | Cl | Br | CH 3 |
| I-166 | 3,4-difluorophenyl | CH 3 | Cl | Br | CF 3 |
| I-167 | 3,4-difluorophenyl | CH 3 | Cl | Br | OCF 3 |
| I-168 | 3,4-difluorophenyl | CH 3 | Cl | Br | OCHF 2 |
| I-169 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | SCH 3 | I | I |
| I-170 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | SCH 3 | Br | Br |
| I-171 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | SCH 3 | Cl | Cl |
| I-172 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | SCH 3 | F | F |
| I-173 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | SCH 3 | Br | CH 3 |
| I-174 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | SCH 3 | Br | CF 3 |
| I-175 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | SCH 3 | Br | OCF 3 |
| I-176 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | SCH 3 | Br | OCHF 2 |
| I-177 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | CH 3 | I | I |
| I-178 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | CH 3 | Br | Br |
| I-179 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | CH 3 | Cl | Cl |
| I-180 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | CH 3 | F | F |
| I-181 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | CH 3 | Br | CH 3 |
| I-182 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | CH 3 | Br | CF 3 |
| I-183 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | CH 3 | Br | OCF 3 |
| I-184 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | CH 3 | Br | OCHF 2 |
| I-185 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | H | I | I |
| I-186 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | H | Br | Br |
| I-187 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | H | Cl | Cl |
| I-188 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | H | F | F |
| I-189 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | H | Br | CH 3 |
| I-190 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | H | Br | CF 3 |
| I-191 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | H | Br | OCF 3 |
| I-192 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | H | Br | OCHF 2 |
| I-193 | 2,4-difluorophenyl | CH 3 | Cl | I | I |
| I-194 | 2,4-difluorophenyl | CH 3 | Cl | Br | Br |
| I-195 | 2,4-difluorophenyl | CH 3 | Cl | Cl | Cl |
| I-196 | 2,4-difluorophenyl | CH 3 | Cl | F | F |
| I-197 | 2,4-difluorophenyl | CH 3 | Cl | Br | CH 3 |
| I-198 | 2,4-difluorophenyl | CH 3 | Cl | Br | CF 3 |
| I-199 | 2,4-difluorophenyl | CH 3 | Cl | Br | OCF 3 |
| I-200 | 2,4-difluorophenyl | CH 3 | Cl | Br | OCHF 2 |
| I-201 | 2,4-difluorophenyl | CH 3 | Br | I | I |
| I-202 | 2,4-difluorophenyl | CH 3 | Br | Br | Br |
| I-203 | 2,4-difluorophenyl | CH 3 | Br | Cl | Cl |
| I-204 | 2,4-difluorophenyl | CH 3 | Br | F | F |
| I-205 | 2,4-difluorophenyl | CH 3 | Br | Br | CH 3 |
| I-206 | 2,4-difluorophenyl | CH 3 | Br | Br | CF 3 |
| I-207 | 2,4-difluorophenyl | CH 3 | Br | Br | OCF 3 |
| I-208 | 2,4-difluorophenyl | CH 3 | Br | Br | OCHF 2 |
| I-209 | 2,4-difluorophenyl | CH 3 | SCH 3 | I | I |
| I-210 | 2,4-difluorophenyl | CH 3 | SCH 3 | Br | Br |
| I-211 | 2,4-difluorophenyl | CH 3 | SCH 3 | Cl | Cl |
| I-212 | 2,4-difluorophenyl | CH 3 | SCH 3 | F | F |
| I-213 | 2,4-difluorophenyl | CH 3 | SCH 3 | Br | CH 3 |
| I-214 | 2,4-difluorophenyl | CH 3 | SCH 3 | Br | CF 3 |
| I-215 | 2,4-difluorophenyl | CH 3 | SCH 3 | Br | OCF 3 |
| I-216 | 2,4-difluorophenyl | CH 3 | SCH 3 | Br | OCHF 2 |
| I-217 | 3,5-dichlorophenyl | CH 3 | Cl | I | I |
| I-218 | 3,5-dichlorophenyl | CH 3 | Cl | Br | Br |
| I-219 | 3,5-dichlorophenyl | CH 3 | Cl | Cl | Cl |
| I-220 | 3,5-dichlorophenyl | CH 3 | Cl | F | F |
| I-221 | 3,5-dichlorophenyl | CH 3 | Cl | Br | CH 3 |
| I-222 | 3,5-dichlorophenyl | CH 3 | Cl | Br | CF 3 |
| I-223 | 3,5-dichlorophenyl | CH 3 | Cl | Br | OCF 3 |
| I-224 | 3,5-dichlorophenyl | CH 3 | Cl | Br | OCHF 2 |
| I-225 | 3,5-dichlorophenyl | CH 3 | Br | I | I |
| I-226 | 3,5-dichlorophenyl | CH 3 | Br | Br | Br |
| I-227 | 3,5-dichlorophenyl | CH 3 | Br | Cl | Cl |
| I-228 | 3,5-dichlorophenyl | CH 3 | Br | F | F |
| I-229 | 3,5-dichlorophenyl | CH 3 | Br | Br | CH 3 |
| I-230 | 3,5-dichlorophenyl | CH 3 | Br | Br | CF 3 |
| I-231 | 3,5-dichlorophenyl | CH 3 | Br | Br | OCF 3 |
| I-232 | 3,5-dichlorophenyl | CH 3 | Br | Br | OCHF 2 |
| I-233 | 3,5-dichlorophenyl | CH 3 | SCH 3 | I | I |
| I-234 | 3,5-dichlorophenyl | CH 3 | SCH 3 | Br | Br |
| I-235 | 3,5-dichlorophenyl | CH 3 | SCH 3 | Cl | Cl |
| I-236 | 3,5-dichlorophenyl | CH 3 | SCH 3 | F | F |
| I-237 | 3,5-dichlorophenyl | CH 3 | SCH 3 | Br | CH 3 |
| I-238 | 3,5-dichlorophenyl | CH 3 | SCH 3 | Br | CF 3 |
| I-239 | 3,5-dichlorophenyl | CH 3 | SCH 3 | Br | OCF 3 |
| I-240 | 3,5-dichlorophenyl | CH 3 | SCH 3 | Br | OCHF 2 |
| I-241 | 3,4-dichlorophenyl | CH 3 | Cl | I | I |
| I-242 | 3,4-dichlorophenyl | CH 3 | Cl | Br | Br |
| I-243 | 3,4-dichlorophenyl | CH 3 | Cl | Cl | Cl |
| I-244 | 3,4-dichlorophenyl | CH 3 | Cl | F | F |
| I-245 | 3,4-dichlorophenyl | CH 3 | Cl | Br | CH 3 |
| I-246 | 3,4-dichlorophenyl | CH 3 | Cl | Br | CF 3 |
| I-247 | 3,4-dichlorophenyl | CH 3 | Cl | Br | OCF 3 |
| I-248 | 3,4-dichlorophenyl | CH 3 | Cl | Br | OCHF 2 |
| I-249 | 3,4-dichlorophenyl | CH 3 | Br | I | I |
| I-250 | 3,4-dichlorophenyl | CH 3 | Br | Br | Br |
| I-251 | 3,4-dichlorophenyl | CH 3 | Br | Cl | Cl |
| I-252 | 3,4-dichlorophenyl | CH 3 | Br | F | F |
| I-253 | 3,4-dichlorophenyl | CH 3 | Br | Br | CH 3 |
| I-254 | 3,4-dichlorophenyl | CH 3 | Br | Br | CF 3 |
| I-255 | 3,4-dichlorophenyl | CH 3 | Br | Br | OCF 3 |
| I-256 | 3,4-dichlorophenyl | CH 3 | Br | Br | OCHF 2 |
| I-257 | 3,4-dichlorophenyl | CH 3 | SCH 3 | I | I |
| I-258 | 3,4-dichlorophenyl | CH 3 | SCH 3 | Br | Br |
| I-259 | 3,4-dichlorophenyl | CH 3 | SCH 3 | Cl | Cl |
| I-260 | 3,4-dichlorophenyl | CH 3 | SCH 3 | F | F |
| I-261 | 3,4-dichlorophenyl | CH 3 | SCH 3 | Br | CH 3 |
| I-262 | 3,4-dichlorophenyl | CH 3 | SCH 3 | Br | CF 3 |
| I-263 | 3,4-dichlorophenyl | CH 3 | SCH 3 | Br | OCF 3 |
| I-264 | 3,4-dichlorophenyl | CH 3 | SCH 3 | Br | OCHF 2 |
| I-265 | 4-trifluoromethoxyphenyl | CH 3 | Cl | I | I |
| I-266 | 4-trifluoromethoxyphenyl | CH 3 | Cl | Br | Br |
| I-267 | 4-trifluoromethoxyphenyl | CH 3 | Cl | Cl | Cl |
| I-268 | 4-trifluoromethoxyphenyl | CH 3 | Cl | F | F |
| I-269 | 4-trifluoromethoxyphenyl | CH 3 | Cl | Br | CH 3 |
| I-270 | 4-trifluoromethoxyphenyl | CH 3 | Cl | Br | CF 3 |
| I-271 | 4-trifluoromethoxyphenyl | CH 3 | Cl | Br | OCF 3 |
| I-272 | 4-trifluoromethoxyphenyl | CH 3 | Cl | Br | OCHF 2 |
| I-273 | 4-trifluoromethoxyphenyl | CH 3 | Br | I | I |
| I-274 | 4-trifluoromethoxyphenyl | CH 3 | Br | Br | Br |
| I-275 | 4-trifluoromethoxyphenyl | CH 3 | Br | Cl | Cl |
| I-276 | 4-trifluoromethoxyphenyl | CH 3 | Br | F | F |
| I-277 | 4-trifluoromethoxyphenyl | CH 3 | Br | Br | CH 3 |
| I-278 | 4-trifluoromethoxyphenyl | CH 3 | Br | Br | CF 3 |
| I-279 | 4-trifluoromethoxyphenyl | CH 3 | Br | Br | OCF 3 |
| I-280 | 4-trifluoromethoxyphenyl | CH 3 | Br | Br | OCHF 2 |
| I-281 | 4-trifluoromethoxyphenyl | CH 3 | SCH 3 | I | I |
| I-282 | 4-trifluoromethoxyphenyl | CH 3 | SCH 3 | Br | Br |
| I-283 | 4-trifluoromethoxyphenyl | CH 3 | SCH 3 | Cl | Cl |
| I-284 | 4-trifluoromethoxyphenyl | CH 3 | SCH 3 | F | F |
| I-285 | 4-trifluoromethoxyphenyl | CH 3 | SCH 3 | Br | CH 3 |
| I-286 | 4-trifluoromethoxyphenyl | CH 3 | SCH 3 | Br | CF 3 |
| I-287 | 4-trifluoromethoxyphenyl | CH 3 | SCH 3 | Br | OCF 3 |
| I-288 | 4-trifluoromethoxyphenyl | CH 3 | SCH 3 | Br | OCHF 2 |
| I-289 | 4-trifluoromethylthiophenyl | CH 3 | Cl | I | I |
| I-290 | 4-trifluoromethylthiophenyl | CH 3 | Cl | Br | Br |
| I-291 | 4-trifluoromethylthiophenyl | CH 3 | Cl | Cl | Cl |
| I-292 | 4-trifluoromethylthiophenyl | CH 3 | Cl | F | F |
| I-293 | 4-trifluoromethylthiophenyl | CH 3 | Cl | Br | CH 3 |
| I-294 | 4-trifluoromethylthiophenyl | CH 3 | Cl | Br | CF 3 |
| I-295 | 4-trifluoromethylthiophenyl | CH 3 | Cl | Br | OCF 3 |
| I-296 | 4-trifluoromethylthiophenyl | CH 3 | Cl | Br | OCHF 2 |
| I-297 | 4-trifluoromethylthiophenyl | CH 3 | Br | I | I |
| I-298 | 4-trifluoromethylthiophenyl | CH 3 | Br | Br | Br |
| I-299 | 4-trifluoromethylthiophenyl | CH 3 | Br | Cl | Cl |
| I-300 | 4-trifluoromethylthiophenyl | CH 3 | Br | F | F |
| I-301 | 4-trifluoromethylthiophenyl | CH 3 | Br | Br | CH 3 |
| I-302 | 4-trifluoromethylthiophenyl | CH 3 | Br | Br | CF 3 |
| I-303 | 4-trifluoromethylthiophenyl | CH 3 | Br | Br | OCF 3 |
| I-304 | 4-trifluoromethylthiophenyl | CH 3 | Br | Br | OCHF 2 |
| I-305 | 4-trifluoromethylthiophenyl | CH 3 | SCH 3 | I | I |
| I-306 | 4-trifluoromethylthiophenyl | CH 3 | SCH 3 | Br | Br |
| I-307 | 4-trifluoromethylthiophenyl | CH 3 | SCH 3 | Cl | Cl |
| I-308 | 4-trifluoromethylthiophenyl | CH 3 | SCH 3 | F | F |
| I-309 | 4-trifluoromethylthiophenyl | CH 3 | SCH 3 | Br | CH 3 |
| I-310 | 4-trifluoromethylthiophenyl | CH 3 | SCH 3 | Br | CF 3 |
| I-311 | 4-trifluoromethylthiophenyl | CH 3 | SCH 3 | Br | OCF 3 |
| I-312 | 4-trifluoromethylthiophenyl | CH 3 | SCH 3 | Br | OCHF 2 |
| I-313 | 4-nitrophenyl | CH 3 | Cl | I | I |
| I-314 | 4-nitrophenyl | CH 3 | Cl | Br | Br |
| I-315 | 4-nitrophenyl | CH 3 | Cl | Cl | Cl |
| I-316 | 4-nitrophenyl | CH 3 | Cl | F | F |
| I-317 | 4-nitrophenyl | CH 3 | Cl | Br | CH 3 |
| I-318 | 4-nitrophenyl | CH 3 | Cl | Br | CF 3 |
| I-319 | 4-nitrophenyl | CH 3 | Cl | Br | OCF 3 |
| I-320 | 4-nitrophenyl | CH 3 | Cl | Br | OCHF 2 |
| I-321 | 4-nitrophenyl | CH 3 | Br | I | I |
| I-322 | 4-nitrophenyl | CH 3 | Br | Br | Br |
| I-323 | 4-nitrophenyl | CH 3 | Br | Cl | Cl |
| I-324 | 4-nitrophenyl | CH 3 | Br | F | F |
| I-325 | 4-nitrophenyl | CH 3 | Br | Br | CH 3 |
| I-326 | 4-nitrophenyl | CH 3 | Br | Br | CF 3 |
| I-327 | 4-nitrophenyl | CH 3 | Br | Br | OCF 3 |
| I-328 | 4-nitrophenyl | CH 3 | Br | Br | OCHF 2 |
| I-329 | 4-nitrophenyl | CH 3 | SCH 3 | I | I |
| I-330 | 4-nitrophenyl | CH 3 | SCH 3 | Br | Br |
| I-331 | 4-nitrophenyl | CH 3 | SCH 3 | Cl | Cl |
| I-332 | 4-nitrophenyl | CH 3 | SCH 3 | F | F |
| I-333 | 4-nitrophenyl | CH 3 | SCH 3 | Br | CH 3 |
| I-334 | 4-nitrophenyl | CH 3 | SCH 3 | Br | CF 3 |
| I-335 | 4-nitrophenyl | CH 3 | SCH 3 | Br | OCF 3 |
| I-336 | 4-nitrophenyl | CH 3 | SCH 3 | Br | OCHF 2 |
| I-337 | 4-difluoromethoxyphenyl | CH 3 | Cl | I | I |
| I-338 | 4-difluoromethoxyphenyl | CH 3 | Cl | Br | Br |
| I-339 | 4-difluoromethoxyphenyl | CH 3 | Cl | Cl | Cl |
| I-340 | 4-difluoromethoxyphenyl | CH 3 | Cl | F | F |
| I-341 | 4-difluoromethoxyphenyl | CH 3 | Cl | Br | CH 3 |
| I-342 | 4-difluoromethoxyphenyl | CH 3 | Cl | Br | CF 3 |
| I-343 | 4-difluoromethoxyphenyl | CH 3 | Cl | Br | OCF 3 |
| I-344 | 4-difluoromethoxyphenyl | CH 3 | Cl | Br | OCHF 2 |
| I-345 | 4-difluoromethoxyphenyl | CH 3 | Br | I | I |
| I-346 | 4-difluoromethoxyphenyl | CH 3 | Br | Br | Br |
| I-347 | 4-difluoromethoxyphenyl | CH 3 | Br | Cl | Cl |
| I-348 | 4-difluoromethoxyphenyl | CH 3 | Br | F | F |
| I-349 | 4-difluoromethoxyphenyl | CH 3 | Br | Br | CH 3 |
| I-350 | 4-difluoromethoxyphenyl | CH 3 | Br | Br | CF 3 |
| I-351 | 4-difluoromethoxyphenyl | CH 3 | Br | Br | OCF 3 |
| I-352 | 4-difluoromethoxyphenyl | CH 3 | Br | Br | OCHF 2 |
| I-353 | 4-difluoromethoxyphenyl | CH 3 | SCH 3 | I | I |
| I-354 | 4-difluoromethoxyphenyl | CH 3 | SCH 3 | Br | Br |
| I-355 | 4-difluoromethoxyphenyl | CH 3 | SCH 3 | Cl | Cl |
| I-356 | 4-difluoromethoxyphenyl | CH 3 | SCH 3 | F | F |
| I-357 | 4-difluoromethoxyphenyl | CH 3 | SCH 3 | Br | CH 3 |
| I-358 | 4-difluoromethoxyphenyl | CH 3 | SCH 3 | Br | CF 3 |
| I-359 | 4-difluoromethoxyphenyl | CH 3 | SCH 3 | Br | OCF 3 |
| I-360 | 4-difluoromethoxyphenyl | CH 3 | SCH 3 | Br | OCHF 2 |
| I-361 | 4-chlorophenyl | CH 3 | Cl | I | I |
| I-362 | 4-chlorophenyl | CH 3 | Cl | Br | Br |
| I-363 | 4-chlorophenyl | CH 3 | Cl | Cl | Cl |
| I-364 | 4-chlorophenyl | CH 3 | Cl | F | F |
| I-365 | 4-chlorophenyl | CH 3 | Cl | Br | CH 3 |
| I-366 | 4-chlorophenyl | CH 3 | Cl | Br | CF 3 |
| I-367 | 4-chlorophenyl | CH 3 | Cl | Br | OCF 3 |
| I-368 | 4-chlorophenyl | CH 3 | Cl | Br | OCHF 2 |
| I-369 | 4-chlorophenyl | CH 3 | Br | I | I |
| I-370 | 4-chlorophenyl | CH 3 | Br | Br | Br |
| I-371 | 4-chlorophenyl | CH 3 | Br | Cl | Cl |
| I-372 | 4-chlorophenyl | CH 3 | Br | F | F |
| I-373 | 4-chlorophenyl | CH 3 | Br | Br | CH 3 |
| I-374 | 4-chlorophenyl | CH 3 | Br | Br | CF 3 |
| I-375 | 4-chlorophenyl | CH 3 | Br | Br | OCF 3 |
| I-376 | 4-chlorophenyl | CH 3 | Br | Br | OCHF 2 |
| I-377 | 4-chlorophenyl | CH 3 | SCH 3 | I | I |
| I-378 | 4-chlorophenyl | CH 3 | SCH 3 | Br | Br |
| I-379 | 4-chlorophenyl | CH 3 | SCH 3 | Cl | Cl |
| I-380 | 4-chlorophenyl | CH 3 | SCH 3 | F | F |
| I-381 | 4-chlorophenyl | CH 3 | SCH 3 | Br | CH 3 |
| I-382 | 4-chlorophenyl | CH 3 | SCH 3 | Br | CF 3 |
| I-383 | 4-chlorophenyl | CH 3 | SCH 3 | Br | OCF 3 |
| I-384 | 4-chlorophenyl | CH 3 | SCH 3 | Br | OCHF 2 |
| I-385 | 3-trifluoromethylphenyl | CH 3 | Cl | I | I |
| I-386 | 3-trifluoromethylphenyl | CH 3 | Cl | Br | Br |
| I-387 | 3-trifluoromethylphenyl | CH 3 | Cl | Cl | Cl |
| I-388 | 3-trifluoromethylphenyl | CH 3 | Cl | F | F |
| I-389 | 3-trifluoromethylphenyl | CH 3 | Cl | Br | CH 3 |
| I-390 | 3-trifluoromethylphenyl | CH 3 | Cl | Br | CF 3 |
| I-391 | 3-trifluoromethylphenyl | CH 3 | Cl | Br | OCF 3 |
| I-392 | 3-trifluoromethylphenyl | CH 3 | Cl | Br | OCHF 2 |
| I-393 | 3-trifluoromethylphenyl | CH 3 | Br | I | I |
| I-394 | 3-trifluoromethylphenyl | CH 3 | Br | Br | Br |
| I-395 | 3-trifluoromethylphenyl | CH 3 | Br | Cl | Cl |
| I-396 | 3-trifluoromethylphenyl | CH 3 | Br | F | F |
| I-397 | 3-trifluoromethylphenyl | CH 3 | Br | Br | CH 3 |
| I-398 | 3-trifluoromethylphenyl | CH 3 | Br | Br | CF 3 |
| I-399 | 3-trifluoromethylphenyl | CH 3 | Br | Br | OCF 3 |
| I-400 | 3-trifluoromethylphenyl | CH 3 | Br | Br | OCHF 2 |
| I-401 | 3-trifluoromethylphenyl | CH 3 | SCH 3 | I | I |
| I-402 | 3-trifluoromethylphenyl | CH 3 | SCH 3 | Br | Br |
| I-403 | 3-trifluoromethylphenyl | CH 3 | SCH 3 | Cl | Cl |
| I-404 | 3-trifluoromethylphenyl | CH 3 | SCH 3 | F | F |
| I-405 | 3-trifluoromethylphenyl | CH 3 | SCH 3 | Br | CH 3 |
| I-406 | 3-trifluoromethylphenyl | CH 3 | SCH 3 | Br | CF 3 |
| I-407 | 3-trifluoromethylphenyl | CH 3 | SCH 3 | Br | OCF 3 |
| I-408 | 3-trifluoromethylphenyl | CH 3 | SCH 3 | Br | OCHF 2 |
| I-409 | 3-trifluoromethoxyphenyl | CH 3 | Cl | I | I |
| I-410 | 3-trifluoromethoxyphenyl | CH 3 | Cl | Br | Br |
| I-411 | 3-trifluoromethoxyphenyl | CH 3 | Cl | Cl | Cl |
| I-412 | 3-trifluoromethoxyphenyl | CH 3 | Cl | F | F |
| I-413 | 3-trifluoromethoxyphenyl | CH 3 | Cl | Br | CH 3 |
| I-414 | 3-trifluoromethoxyphenyl | CH 3 | Cl | Br | CF 3 |
| I-415 | 3-trifluoromethoxyphenyl | CH 3 | Cl | Br | OCF 3 |
| I-416 | 3-trifluoromethoxyphenyl | CH 3 | Cl | Br | OCHF 2 |
| I-417 | 3-trifluoromethoxyphenyl | CH 3 | Br | I | I |
| I-418 | 3-trifluoromethoxyphenyl | CH 3 | Br | Br | Br |
| I-419 | 3-trifluoromethoxyphenyl | CH 3 | Br | Cl | Cl |
| I-420 | 3-trifluoromethoxyphenyl | CH 3 | Br | F | F |
| I-421 | 3-trifluoromethoxyphenyl | CH 3 | Br | Br | CH 3 |
| I-422 | 3-trifluoromethoxyphenyl | CH 3 | Br | Br | CF 3 |
| I-423 | 3-trifluoromethoxyphenyl | CH 3 | Br | Br | OCF 3 |
| I-424 | 3-trifluoromethoxyphenyl | CH 3 | Br | Br | OCHF 2 |
| I-425 | 3-trifluoromethoxyphenyl | CH 3 | SCH 3 | I | I |
| I-426 | 3-trifluoromethoxyphenyl | CH 3 | SCH 3 | Br | Br |
| I-427 | 3-trifluoromethoxyphenyl | CH 3 | SCH 3 | Cl | Cl |
| I-428 | 3-trifluoromethoxyphenyl | CH 3 | SCH 3 | F | F |
| I-429 | 3-trifluoromethoxyphenyl | CH 3 | SCH 3 | Br | CH 3 |
| I-430 | 3-trifluoromethoxyphenyl | CH 3 | SCH 3 | Br | CF 3 |
| I-431 | 3-trifluoromethoxyphenyl | CH 3 | SCH 3 | Br | OCF 3 |
| I-432 | 3-trifluoromethoxyphenyl | CH 3 | SCH 3 | Br | OCHF 2 |
| I-433 | 3-methoxyphenyl | CH 3 | Cl | I | I |
| I-434 | 3-methoxyphenyl | CH 3 | Cl | Br | Br |
| I-435 | 3-methoxyphenyl | CH 3 | Cl | Cl | Cl |
| I-436 | 3-methoxyphenyl | CH 3 | Cl | F | F |
| I-437 | 3-methoxyphenyl | CH 3 | Cl | Br | CH 3 |
| I-438 | 3-methoxyphenyl | CH 3 | Cl | Br | CF 3 |
| I-439 | 3-methoxyphenyl | CH 3 | Cl | Br | OCF 3 |
| I-440 | 3-methoxyphenyl | CH 3 | Cl | Br | OCHF 2 |
| I-441 | 3-methoxyphenyl | CH 3 | Br | I | I |
| I-442 | 3-methoxyphenyl | CH 3 | Br | Br | Br |
| I-443 | 3-methoxyphenyl | CH 3 | Br | Cl | Cl |
| I-444 | 3-methoxyphenyl | CH 3 | Br | F | F |
| I-445 | 3-methoxyphenyl | CH 3 | Br | Br | CH 3 |
| I-446 | 3-methoxyphenyl | CH 3 | Br | Br | CF 3 |
| I-447 | 3-methoxyphenyl | CH 3 | Br | Br | OCF 3 |
| I-448 | 3-methoxyphenyl | CH 3 | Br | Br | OCHF 2 |
| I-449 | 3-methoxyphenyl | CH 3 | SCH 3 | I | I |
| I-450 | 3-methoxyphenyl | CH 3 | SCH 3 | Br | Br |
| I-451 | 3-methoxyphenyl | CH 3 | SCH 3 | Cl | Cl |
| I-452 | 3-methoxyphenyl | CH 3 | SCH 3 | F | F |
| I-453 | 3-methoxyphenyl | CH 3 | SCH 3 | Br | CH 3 |
| I-454 | 3-methoxyphenyl | CH 3 | SCH 3 | Br | CF 3 |
| I-455 | 3-methoxyphenyl | CH 3 | SCH 3 | Br | OCF 3 |
| I-456 | 3-methoxyphenyl | CH 3 | SCH 3 | Br | OCHF 2 |
| I-457 | 3-chlorophenyl | CH 3 | Cl | I | I |
| I-458 | 3-chlorophenyl | CH 3 | Cl | Br | Br |
| I-459 | 3-chlorophenyl | CH 3 | Cl | Cl | Cl |
| I-460 | 3-chlorophenyl | CH 3 | Cl | F | F |
| I-461 | 3-chlorophenyl | CH 3 | Cl | Br | CH 3 |
| I-462 | 3-chlorophenyl | CH 3 | Cl | Br | CF 3 |
| I-463 | 3-chlorophenyl | CH 3 | Cl | Br | OCF 3 |
| I-464 | 3-chlorophenyl | CH 3 | Cl | Br | OCHF 2 |
| I-465 | 3-chlorophenyl | CH 3 | Br | I | I |
| I-466 | 3-chlorophenyl | CH 3 | Br | Br | Br |
| I-467 | 3-chlorophenyl | CH 3 | Br | Cl | Cl |
| I-468 | 3-chlorophenyl | CH 3 | Br | F | F |
| I-469 | 3-chlorophenyl | CH 3 | Br | Br | CH 3 |
| I-470 | 3-chlorophenyl | CH 3 | Br | Br | CF 3 |
| I-471 | 3-chlorophenyl | CH 3 | Br | Br | OCF 3 |
| I-472 | 3-chlorophenyl | CH 3 | Br | Br | OCHF 2 |
| I-473 | 3-chlorophenyl | CH 3 | SCH 3 | I | I |
| I-474 | 3-chlorophenyl | CH 3 | SCH 3 | Br | Br |
| I-475 | 3-chlorophenyl | CH 3 | SCH 3 | Cl | Cl |
| I-476 | 3-chlorophenyl | CH 3 | SCH 3 | F | F |
| I-477 | 3-chlorophenyl | CH 3 | SCH 3 | Br | CH 3 |
| I-478 | 3-chlorophenyl | CH 3 | SCH 3 | Br | CF 3 |
| I-479 | 3-chlorophenyl | CH 3 | SCH 3 | Br | OCF 3 |
| I-480 | 3-chlorophenyl | CH 3 | SCH 3 | Br | OCHF 2 |
| I-481 | 3-cyanophenyl | CH 3 | Cl | I | I |
| I-482 | 3-cyanophenyl | CH 3 | Cl | Br | Br |
| I-483 | 3-cyanophenyl | CH 3 | Cl | Cl | Cl |
| I-484 | 3-cyanophenyl | CH 3 | Cl | F | F |
| I-485 | 3-cyanophenyl | CH 3 | Cl | Br | CH 3 |
| I-486 | 3-cyanophenyl | CH 3 | Cl | Br | CF 3 |
| I-487 | 3-cyanophenyl | CH 3 | Cl | Br | OCF 3 |
| I-488 | 3-cyanophenyl | CH 3 | Cl | Br | OCHF 2 |
| I-489 | 3-cyanophenyl | CH 3 | Br | I | I |
| I-490 | 3-cyanophenyl | CH 3 | Br | Br | Br |
| I-491 | 3-cyanophenyl | CH 3 | Br | Cl | Cl |
| I-492 | 3-cyanophenyl | CH 3 | Br | F | F |
| I-493 | 3-cyanophenyl | CH 3 | Br | Br | CH 3 |
| I-494 | 3-cyanophenyl | CH 3 | Br | Br | CF 3 |
| I-495 | 3-cyanophenyl | CH 3 | Br | Br | OCF 3 |
| I-496 | 3-cyanophenyl | CH 3 | Br | Br | OCHF 2 |
| I-497 | 3-cyanophenyl | CH 3 | SCH 3 | I | I |
| I-498 | 3-cyanophenyl | CH 3 | SCH 3 | Br | Br |
| I-499 | 3-cyanophenyl | CH 3 | SCH 3 | Cl | Cl |
| I-500 | 3-cyanophenyl | CH 3 | SCH 3 | F | F |
| I-501 | 3-cyanophenyl | CH 3 | SCH 3 | Br | CH 3 |
| I-502 | 3-cyanophenyl | CH 3 | SCH 3 | Br | CF 3 |
| I-503 | 3-cyanophenyl | CH 3 | SCH 3 | Br | OCF 3 |
| I-504 | 3-cyanophenyl | CH 3 | SCH 3 | Br | OCHF 2 |
| I-505 | 2-fluorophenyl | CH 3 | Cl | I | I |
| I-506 | 2-fluorophenyl | CH 3 | Cl | Br | Br |
| I-507 | 2-fluorophenyl | CH 3 | Cl | Cl | Cl |
| I-508 | 2-fluorophenyl | CH 3 | Cl | F | F |
| I-509 | 2-fluorophenyl | CH 3 | Cl | Br | CH 3 |
| I-510 | 2-fluorophenyl | CH 3 | Cl | Br | CF 3 |
| I-511 | 2-fluorophenyl | CH 3 | Cl | Br | OCF 3 |
| I-512 | 2-fluorophenyl | CH 3 | Cl | Br | OCHF 2 |
| I-513 | 2-fluorophenyl | CH 3 | Br | I | I |
| I-514 | 2-fluorophenyl | CH 3 | Br | Br | Br |
| I-515 | 2-fluorophenyl | CH 3 | Br | Cl | Cl |
| I-516 | 2-fluorophenyl | CH 3 | Br | F | F |
| I-517 | 2-fluorophenyl | CH 3 | Br | Br | CH 3 |
| I-518 | 2-fluorophenyl | CH 3 | Br | Br | CF 3 |
| I-519 | 2-fluorophenyl | CH 3 | Br | Br | OCF 3 |
| I-520 | 2-fluorophenyl | CH 3 | Br | Br | OCHF 2 |
| I-521 | 2-fluorophenyl | CH 3 | SCH 3 | I | I |
| I-522 | 2-fluorophenyl | CH 3 | SCH 3 | Br | Br |
| I-523 | 2-fluorophenyl | CH 3 | SCH 3 | Cl | Cl |
| I-524 | 2-fluorophenyl | CH 3 | SCH 3 | F | F |
| I-525 | 2-fluorophenyl | CH 3 | SCH 3 | Br | CH 3 |
| I-526 | 2-fluorophenyl | CH 3 | SCH 3 | Br | CF 3 |
| I-527 | 2-fluorophenyl | CH 3 | SCH 3 | Br | OCF 3 |
| I-528 | 2-fluorophenyl | CH 3 | SCH 3 | Br | OCHF 2 |
| I-529 | 2-methoxyphenyl | CH 3 | Cl | I | I |
| I-530 | 2-methoxyphenyl | CH 3 | Cl | Br | Br |
| I-531 | 2-methoxyphenyl | CH 3 | Cl | Cl | Cl |
| I-532 | 2-methoxyphenyl | CH 3 | Cl | F | F |
| I-533 | 2-methoxyphenyl | CH 3 | Cl | Br | CH 3 |
| I-534 | 2-methoxyphenyl | CH 3 | Cl | Br | CF 3 |
| I-535 | 2-methoxyphenyl | CH 3 | Cl | Br | OCF 3 |
| I-536 | 2-methoxyphenyl | CH 3 | Cl | Br | OCHF 2 |
| I-537 | 2-methoxyphenyl | CH 3 | Br | I | I |
| I-538 | 2-methoxyphenyl | CH 3 | Br | Br | Br |
| I-539 | 2-methoxyphenyl | CH 3 | Br | Cl | Cl |
| I-540 | 2-methoxyphenyl | CH 3 | Br | F | F |
| I-541 | 2-methoxyphenyl | CH 3 | Br | Br | CH 3 |
| I-542 | 2-methoxyphenyl | CH 3 | Br | Br | CF 3 |
| I-543 | 2-methoxyphenyl | CH 3 | Br | Br | OCF 3 |
| I-544 | 2-methoxyphenyl | CH 3 | Br | Br | OCHF 2 |
| I-545 | 2-methoxyphenyl | CH 3 | SCH 3 | I | I |
| I-546 | 2-methoxyphenyl | CH 3 | SCH 3 | Br | Br |
| I-547 | 2-methoxyphenyl | CH 3 | SCH 3 | Cl | Cl |
| I-548 | 2-methoxyphenyl | CH 3 | SCH 3 | F | F |
| I-549 | 2-methoxyphenyl | CH 3 | SCH 3 | Br | CH 3 |
| I-550 | 2-methoxyphenyl | CH 3 | SCH 3 | Br | CF 3 |
| I-551 | 2-methoxyphenyl | CH 3 | SCH 3 | Br | OCF 3 |
| I-552 | 2-methoxyphenyl | CH 3 | SCH 3 | Br | OCHF 2 |
| I-553 | 3, 5-difluorophenyl | CH 3 | Cl | I | I |
| I-554 | 3, 5-difluorophenyl | CH 3 | Cl | Br | Br |
| I-555 | 3, 5-difluorophenyl | CH 3 | Cl | Cl | Cl |
| I-556 | 3, 5-difluorophenyl | CH 3 | Cl | F | F |
| I-557 | 3, 5-difluorophenyl | CH 3 | Cl | Br | CH 3 |
| I-558 | 3, 5-difluorophenyl | CH 3 | Cl | Br | CF 3 |
| I-559 | 3, 5-difluorophenyl | CH 3 | Cl | Br | OCF 3 |
| I-560 | 3, 5-difluorophenyl | CH 3 | Cl | Br | OCHF 2 |
| I-561 | 3, 5-difluorophenyl | CH 3 | Br | I | I |
| I-562 | 3, 5-difluorophenyl | CH 3 | Br | Br | Br |
| I-563 | 3, 5-difluorophenyl | CH 3 | Br | Cl | Cl |
| I-564 | 3, 5-difluorophenyl | CH 3 | Br | F | F |
| I-565 | 3, 5-difluorophenyl | CH 3 | Br | Br | CH 3 |
| I-566 | 3, 5-difluorophenyl | CH 3 | Br | Br | CF 3 |
| I-567 | 3, 5-difluorophenyl | CH 3 | Br | Br | OCF 3 |
| I-568 | 3, 5-difluorophenyl | CH 3 | Br | Br | OCHF 2 |
| I-569 | 3, 5-difluorophenyl | CH 3 | SCH 3 | I | I |
| I-570 | 3, 5-difluorophenyl | CH 3 | SCH 3 | Br | Br |
| I-571 | 3, 5-difluorophenyl | CH 3 | SCH 3 | Cl | Cl |
| I-572 | 3, 5-difluorophenyl | CH 3 | SCH 3 | F | F |
| I-573 | 3, 5-difluorophenyl | CH 3 | SCH 3 | Br | CH 3 |
| I-574 | 3, 5-difluorophenyl | CH 3 | SCH 3 | Br | CF 3 |
| I-575 | 3,5-difluorophenyl | CH 3 | SCH 3 | Br | OCF 3 |
| I-576 | 3,5-difluorophenyl | CH 3 | SCH 3 | Br | OCHF 2 |
| I-577 | 3,4,5-trifluorophenyl | CH 3 | Cl | I | I |
| I-578 | 3,4,5-trifluorophenyl | CH 3 | Cl | Br | Br |
| I-579 | 3,4,5-trifluorophenyl | CH 3 | Cl | Cl | Cl |
| I-580 | 3,4,5-trifluorophenyl | CH 3 | Cl | F | F |
| I-581 | 3,4,5-trifluorophenyl | CH 3 | Cl | Br | CH 3 |
| I-582 | 3,4,5-trifluorophenyl | CH 3 | Cl | Br | CF 3 |
| I-583 | 3,4,5-trifluorophenyl | CH 3 | Cl | Br | OCF 3 |
| I-584 | 3,4,5-trifluorophenyl | CH 3 | Cl | Br | OCHF 2 |
| I-585 | 3,4,5-trifluorophenyl | CH 3 | Br | I | I |
| I-586 | 3,4,5-trifluorophenyl | CH 3 | Br | Br | Br |
| I-587 | 3,4,5-trifluorophenyl | CH 3 | Br | Cl | Cl |
| I-588 | 3,4,5-trifluorophenyl | CH 3 | Br | F | F |
| I-589 | 3,4,5-trifluorophenyl | CH 3 | Br | Br | CH 3 |
| I-590 | 3,4,5-trifluorophenyl | CH 3 | Br | Br | CF 3 |
| I-591 | 3,4,5-trifluorophenyl | CH 3 | Br | Br | OCF 3 |
| I-592 | 3,4,5-trifluorophenyl | CH 3 | Br | Br | OCHF 2 |
| I-593 | 3,4,5-trifluorophenyl | CH 3 | SCH 3 | I | I |
| I-594 | 3,4,5-trifluorophenyl | CH 3 | SCH 3 | Br | Br |
| I-595 | 3,4,5-trifluorophenyl | CH 3 | SCH 3 | Cl | Cl |
| I-596 | 3,4,5-trifluorophenyl | CH 3 | SCH 3 | F | F |
| I-597 | 3,4,5-trifluorophenyl | CH 3 | SCH 3 | Br | CH 3 |
| I-598 | 3,4,5-trifluorophenyl | CH 3 | SCH 3 | Br | CF 3 |
| I-599 | 3,4,5-trifluorophenyl | CH 3 | SCH 3 | Br | OCF 3 |
| I-600 | 3,4,5-trifluorophenyl | CH 3 | SCH 3 | Br | OCHF 2 |
| I-601 | 3,4-difluorophenyl | CH 3 | SCH 3 | I | I |
| I-602 | 3,4-difluorophenyl | CH 3 | SCH 3 | Br | Br |
| I-603 | 3,4-difluorophenyl | CH 3 | SCH 3 | Cl | Cl |
| I-604 | 3,4-difluorophenyl | CH 3 | SCH 3 | F | F |
| I-605 | 3,4-difluorophenyl | CH 3 | SCH 3 | Br | CH 3 |
| I-606 | 3,4-difluorophenyl | CH 3 | SCH 3 | Br | CF 3 |
| I-607 | 3,4-difluorophenyl | CH 3 | SCH 3 | Br | OCF 3 |
| I-608 | 3,4-difluorophenyl | CH 3 | SCH 3 | Br | OCHF 2 |
| I-609 | 4-fluorophenyl | CH 3 | SCH 3 | I | I |
| I-610 | 4-fluorophenyl | CH 3 | SCH 3 | Br | Br |
| I-611 | 4-fluorophenyl | CH 3 | SCH 3 | Cl | Cl |
| I-612 | 4-fluorophenyl | CH 3 | SCH 3 | F | F |
| I-613 | 4-fluorophenyl | CH 3 | SCH 3 | Br | CH 3 |
| I-614 | 4-fluorophenyl | CH 3 | SCH 3 | Br | CF 3 |
| I-615 | 4-fluorophenyl | CH 3 | SCH 3 | Br | OCF 3 |
| I-616 | 4-fluorophenyl | CH 3 | SCH 3 | Br | OCHF 2 |
| I-617 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | SC 2H 5 | Br | CF 3 |
| I-618 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | SC 2H 5 | Br | OCHF 2 |
| I-619 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | 1H-1,2,4-triazol-1-yl | Br | CF 3 |
| I-620 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | 1H-1,2,4-triazol-1-yl | Br | OCHF 2 |
| I-621 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | 2H-1,2,3-triazol-2-yl | Br | CF 3 |
| I-622 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | 2H-1,2,3-triazol-2-yl | Br | OCHF 2 |
| I-623 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | morpholin-4-yl | Br | CF 3 |
| I-624 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | morpholin-4-yl | Br | OCHF 2 |
| I-625 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | OC 2H 5 | Br | CF 3 |
| I-626 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | OC 2H 5 | Br | OCHF 2 |
| I-627 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | NHCH 3 | Br | CF 3 |
| I-628 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | NHCH 3 | Br | OCHF 2 |
| I-629 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | 4-ethylpiperazin-1-yl | Br | CF 3 |
| I-630 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | 4-ethylpiperazin-1-yl | Br | OCHF 2 |
| I-631 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | SC(CH 3) 3 | Br | CF 3 |
| I-632 | 2,2-difluorobenzo[d][1,3]dioxol-5-yl | CH 3 | SC(CH 3) 3 | Br | OCHF 2 |
| I-633 | 4-cyanophenyl | CH 3 | SC 2H 5 | Br | CF 3 |
| I-634 | 4-cyanophenyl | CH 3 | SC 2H 5 | Br | OCHF 2 |
| I-635 | 4-cyanophenyl | CH 3 | 1H-1,2,4-triazol-1-yl | Br | CF 3 |
| I-636 | 4-cyanophenyl | CH 3 | 1H-1,2,4-triazol-1-yl | Br | OCHF 2 |
| I-637 | 4-cyanophenyl | CH 3 | 2H-1,2,3-triazol-2-yl | Br | CF 3 |
| I-638 | 4-cyanophenyl | CH 3 | 2H-1,2,3-triazol-2-yl | Br | OCHF 2 |
| I-639 | 4-cyanophenyl | CH 3 | morpholin-4-yl | Br | CF 3 |
| I-640 | 4-cyanophenyl | CH 3 | morpholin-4-yl | Br | OCHF 2 |
| I-641 | 4-cyanophenyl | CH 3 | OC 2H 5 | Br | CF 3 |
| I-642 | 4-cyanophenyl | CH 3 | OC 2H 5 | Br | OCHF 2 |
| I-643 | 4-cyanophenyl | CH 3 | NHCH 3 | Br | CF 3 |
| I-644 | 4-cyanophenyl | CH 3 | NHCH 3 | Br | OCHF 2 |
| I-645 | 4-cyanophenyl | CH 3 | 4-ethylpiperazin-1-yl | Br | CF 3 |
| I-646 | 4-cyanophenyl | CH 3 | 4-ethylpiperazin-1-yl | Br | OCHF 2 |
| I-647 | 4-cyanophenyl | CH 3 | SC(CH 3) 3 | Br | CF 3 |
| I-648 | 4-cyanophenyl | CH 3 | SC(CH 3) 3 | Br | OCHF 2 |
| I-649 | 4-fluorophenyl | CH 3 | SC 2H 5 | Br | CF 3 |
| I-650 | 4-fluorophenyl | CH 3 | SC 2H 5 | Br | OCHF 2 |
| I-651 | 4-fluorophenyl | CH 3 | 1H-1,2,4-triazol-1-yl | Br | CF 3 |
| I-652 | 4-fluorophenyl | CH 3 | 1H-1,2,4-triazol-1-yl | Br | OCHF 2 |
| I-653 | 4-fluorophenyl | CH 3 | 2H-1,2,3-triazol-2-yl | Br | CF 3 |
| I-654 | 4-fluorophenyl | CH 3 | 2H-1,2,3-triazol-2-yl | Br | OCHF 2 |
| I-655 | 4-fluorophenyl | CH 3 | morpholin-4-yl | Br | CF 3 |
| I-656 | 4-fluorophenyl | CH 3 | morpholin-4-yl | Br | OCHF 2 |
| I-657 | 4-fluorophenyl | CH 3 | OC 2H 5 | Br | CF 3 |
| I-658 | 4-fluorophenyl | CH 3 | OC 2H 5 | Br | OCHF 2 |
| I-659 | 4-fluorophenyl | CH 3 | NHCH 3 | Br | CF 3 |
| I-660 | 4-fluorophenyl | CH 3 | NHCH 3 | Br | OCHF 2 |
| I-661 | 4-fluorophenyl | CH 3 | 4-ethylpiperazin-1-yl | Br | CF 3 |
| I-662 | 4-fluorophenyl | CH 3 | 4-ethylpiperazin-1-yl | Br | OCHF 2 |
| I-663 | 4-fluorophenyl | CH 3 | SC(CH 3) 3 | Br | CF 3 |
| I-664 | 4-fluorophenyl | CH 3 | SC(CH 3) 3 | Br | OCHF 2 |
| I-665 | 4-trifluoromethylphenyl | CH 3 | SC 2H 5 | Br | CF 3 |
| I-666 | 4-trifluoromethylphenyl | CH 3 | SC 2H 5 | Br | OCHF 2 |
| I-667 | 4-trifluoromethylphenyl | CH 3 | 1H-1,2,4-triazol-1-yl | Br | CF 3 |
| I-668 | 4-trifluoromethylphenyl | CH 3 | 1H-1,2,4-triazol-1-yl | Br | OCHF 2 |
| I-669 | 4-trifluoromethylphenyl | CH 3 | 2H-1,2,3-triazol-2-yl | Br | CF 3 |
| I-670 | 4-trifluoromethylphenyl | CH 3 | 2H-1,2,3-triazol-2-yl | Br | OCHF 2 |
| I-671 | 4-trifluoromethylphenyl | CH 3 | morpholin-4-yl | Br | CF 3 |
| I-672 | 4-trifluoromethylphenyl | CH 3 | morpholin-4-yl | Br | OCHF 2 |
| I-673 | 4-trifluoromethylphenyl | CH 3 | OC 2H 5 | Br | CF 3 |
| I-674 | 4-trifluoromethylphenyl | CH 3 | OC 2H 5 | Br | OCHF 2 |
| I-675 | 4-trifluoromethylphenyl | CH 3 | NHCH 3 | Br | CF 3 |
| I-676 | 4-trifluoromethylphenyl | CH 3 | NHCH 3 | Br | OCHF 2 |
| I-677 | 4-trifluoromethylphenyl | CH 3 | 4-ethylpiperazin-1-yl | Br | CF 3 |
| I-678 | 4-trifluoromethylphenyl | CH 3 | 4-ethylpiperazin-1-yl | Br | OCHF 2 |
| I-679 | 4-trifluoromethylphenyl | CH 3 | SC(CH 3) 3 | Br | CF 3 |
| I-680 | 4-trifluoromethylphenyl | CH 3 | SC(CH 3) 3 | Br | OCHF 2 |
| I-681 | 4-cyanophenyl | CH 3 | Br | I | I |
| I-682 | 4-cyanophenyl | CH 3 | Br | Br | Br |
| I-683 | 4-cyanophenyl | CH 3 | Br | Cl | Cl |
| I-684 | 4-cyanophenyl | CH 3 | Br | F | F |
| I-685 | 4-cyanophenyl | CH 3 | Br | Br | CH 3 |
| I-686 | 4-cyanophenyl | CH 3 | Br | Br | CF 3 |
| I-687 | 4-cyanophenyl | CH 3 | Br | Br | OCF 3 |
| I-688 | 4-cyanophenyl | CH 3 | Br | Br | OCHF 2 |
部分化合物的
1H NMR(600MHz,CDCl
3,ppm)及物化性质如下：
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。
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。
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。
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。
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。
本发明所具有的优点：
本发明化合物结构新颖，兼具杀虫和杀螨，用途广泛。
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。
合成实施例
实施例1：化合物I-38的制备
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
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)。
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).
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
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)。
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).
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
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)。
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).
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
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)。
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).
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
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)。
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).
实施例2：化合物I-46的制备
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)。
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).
实施例3：化合物I-122的制备
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
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)。
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).
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
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)
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).
实施例4：化合物I-128的制备
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
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)。
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).
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
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)。
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).
实施例5：化合物I-130的制备
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)。
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).
实施例6：化合物I-176的制备
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％。
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).
实施例7：化合物I-618的制备
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％。
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).
实施例8：化合物I-620的制备
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％。
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).
实施例9：化合物I-626的制备
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％。
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).
实施例10：化合物I-628的制备
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％。
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).
实施例11：化合物I-630的制备
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％。
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).
实施例12：化合物I-632的制备
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％。
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).
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。
生物活性测定
实施例13杀虫活性测定
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。
实施例13.1对粘虫活性的测定
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。
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％。
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％。
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％。
实施例13.2对小菜蛾活性的测定
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。
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％。
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％。
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％。
实施例13.3对桃蚜活性的测定
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。
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％。
实施例14杀螨活性测定
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％。
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。
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％。
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。
Claims (7)
- 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：
式中：Q选自
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；m选自0、1、2、3、4或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；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 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；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。 - 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：Q选自
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；m选自0、1、2、3、4或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；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 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；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。 - 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：Q选自
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；m选自0、1、2或3；X 2和X 3可相同或不同的分别选自H或卤素；R 1选自H或C 1-C 3烷基；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；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。 - 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：Q选自
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；m选自0、1或2；X 2和X 3均选自F；R 1选自H或甲基；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；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。 - 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：Q选自
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；m选自0、1或2；X 2和X 3均选自F；R 1选自甲基；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；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。 - 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。
- 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。
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