AMIDE DERIVATIVES, PROCESS FOR PREPARATION THEREOF AND USE THEREOF AS INSECTICIDE

Information

  • Patent Application
  • 20190382366
  • Publication Number
    20190382366
  • Date Filed
    August 27, 2019
    5 years ago
  • Date Published
    December 19, 2019
    5 years ago
Abstract
A compound represented by Formula (1):
Description
TECNICAL FIELD

The present invention relates to a compound represented by Formula (1):




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wherein A1, A2, A3 and A4 each represent a carbon atom, a nitrogen atom or an oxidized nitrogen atom;


R1 and R2 each represent a hydrogen atom, an optionally substituted alkyl group or an optionally substituted C1-C4 alkylcarbonyl group;


G1 and G2 each represent an oxygen atom or a sulfur atom;


X, which may be identical or different, represents a hydrogen atom, a halogen atom, a C1-C3 alkyl group or a trifluoromethyl group;


n is an integer of 0 to 4; and


Q1 and Q2 each represent an optionally substituted phenyl group, an optionally substituted naphthyl group or an optionally substituted heterocyclic group,


an insecticide comprising the compound as the active ingredient, and a process for preparation thereof and use thereof.


BACKGROUND ART

International Publication WO 2000/55120 and U.S. Pat. No. 6,548,514 describe a compound similar to the compound of the present invention for the use as medicament, but they do not describe on the insecticidal activity of the compound. The compound clearly does not fall within the scope of claims of the present invention.


International Publication WO 2000/7980 describes a compound similar to the compound of the present invention for the use as medicament, but it does not describe on the insecticidal activity of the compound. The compound clearly does not fall within the scope of claims of the present invention.


US Patent Laid-Open No. 2002-032238 describes a compound similar to the compound of the present invention for the use as medicament, but it does not describe on the insecticidal activity of the compound. The compound clearly does not fall within the scope of claims of the present invention.


DISCLOSURE OF THE INVENTION

The object of the present invention is to provide a pesticide having a high insecticidal efficacy. Another object of the present invention is to provide a compound represented by Formula (1), a process for preparation of the compound, an insectcide comprising the compound as an active ingredient, and a process for controlling pests by using a combination of the compound with another pesticide and/or a fungicide.


The inventors have conducted intensive studies to solve the above problems and discovered that the compound of the invention is a novel compound unknown in the documents and has remarkably excellent insecticidal effects, thus finding a novel application of the compound as a pesticide. Further, they also discovered that a compound unknown in the documents is a useful intermediate for the preparation of the compound of the present invention. As a result, they have completed the present invention.


The subject of the invention is as follows.


[1] A compound represented by Formula (1):




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wherein A1, A2, A3 and A4 each represent a carbon atom, a nitrogen atom or an oxidized nitrogen atom;


R1 and R2 each represent a hydrogen atom, an optionally substituted alkyl group or an optionally substituted C1-C4 alkylcarbonyl group;


G1 and G2 each represent an oxygen atom or a sulfur atom;


Xs, which may be identical or different each other, represent a hydrogen atom, a halogen atom, a C1-C3 alkyl group or a trifluoromethyl group;


n is an integer of 0 to 4; and


Q1 represents an optionally substituted phenyl group, an optionally substituted naphthyl group or an optionally substituted heterocyclic group;


Q2 represents a phenyl group or heterocyclic group having one or more substituents, at least one of the substituent being any of a C1-C4 haloalkoxy group, a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group and a C1-C6 perfluoroalkylsulfonyl group.


The compound as described in [1] represented by Formula (1), wherein


R1 and R2 are each a hydrogen atom or a C1-C4 alkyl group;


Xs, which may be identical or different each other, are a hydrogen atom, a halogen atom or a trifluoromethyl group;


Q1 is a phenyl group, or a substituted phenyl group having one or more substituents, which may be identical or different, selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4-alkylamino group, a cyano group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group; a heterocyclic group (the heterocyclic group herein represents a pyridyl group, a pyridin-N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrolyl group, a pyrazolyl group or a tetrazolyl group), or a substituted heterocyclic group (which means the same as those described above) having one or more substituents, which may be identical or different, selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4-alkylamino group, a cyano group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group, and a phenyl group;


Q2 is represented by Formula (2):




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(wherein Y1 and Y5, which may be identical or different, each represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y2 and Y4 each represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group);


or by Formula (3):




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(wherein Y6 and Y9, which may be identical or different, each represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y8 represents a C1-C4 haloalkoxy group, a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group).


[3] The compound as described in [2], represented by Formula (1a), which is Formula (1) with A1, A2, A3 and A4 being all carbon atoms:




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wherein R1, R2, G1, G2 and Q1 have the same meanings as those described in [2], and Q2 is represented either by Formula (2):




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(wherein Y1 and Y5, which may be identical or different, each represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y2 and Y4 each represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group);


or by Formula (3):




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(wherein Y6 and Y9, which may be identical or different, each represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y8 represents a C1-C4 haloalkoxy group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group),


wherein in Formula (1a), X1 and X2 each represent a hydrogen atom or a fluorine atom; and


X3 and X4 represent a hydrogen atom.


[4] The compound as described in [3], represented by Formula (1a), wherein


Q1 is a phenyl group; a substituted phenyl group having one or more substituents, Which may be identical or different, selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4-alkylamino group, a cyano group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group; a pyridyl group; or a substituted pyridyl group having one or more substituents, which may be identical or different, selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4-alkylamino group, a cyano group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group.


The compound as described in [1] or [2], represented by Formula (1a), which is Formula (1) with A1, A2, A3 and A4 being all carbon atoms:




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wherein Q2 is represented either by Formula (2):




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(wherein Y1 and Y5, which may be identical or different, each represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a C2-06 perfluoroalkyl group; and Y2 and Y4 each represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group);


or by Formula (3):




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(wherein Y6 and Y9, which may be identical or different, each represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y8 represents a C2-C6 perfluoroalkyl group; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group);


X1 and X2 each represent a hydrogen atom or a fluorine atom;


X3 and X4 represent a hydrogen atom;


one of R1 and R2 is a hydrogen atom, the other is a C1-C4 alkyl group, or both of them are a C1-C4 alkyl group;


G1 and G2 each represent an oxygen atom or a sulfur atom; and


Q1 represents a phenyl group; a substituted phenyl group having one or more substituents, which may be identical or different, selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4-alkylamino group, a cyano group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group; a heterocyclic group (the heterocyclic group herein represents a pyridyl group, a pyridin-N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrolyl group, a pyrazolyl group or a tetrazolyl group); or a substituted heterocyclic group (which means the same as those described above) having one or more substituents, which may be identical or different, selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4-alkylamino group, a cyano group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group.


The compound as described in [5], represented by Formula (1a), wherein


Q1 is a phenyl group; a substituted phenyl group having one or more substituents, which may be identical or different, selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4-alkylamino group, a cyano group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group; a pyridyl group; or a substituted pyridyl group having one or more substituents, which may be identical or different, selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4-alkylamino group, a cyano group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group.


[7] The compound as described in [1] or [2], wherein A1 is a nitrogen atom or an oxidized nitrogen atom; A2, A3 and A4 are a carbon atom; R1 and R2 are each a hydrogen or a C1-C4 alkyl group; X is a hydrogen atom and a fluorine atom; n is 0 or 1; and G1 and G2 are an oxygen atom.


[8] The compound as described in [7], represented by Formula (1), wherein


Q1 is a phenyl group; a substituted phenyl group having one or more substituents, which may be identical or different, selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4-alkylamino group, a cyano group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group; a pyridyl group; or a substituted pyridyl group having one or more substituents, which may be identical or different, selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4-alkylamino group, a cyano group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group.


[9] A compound represented by Formula (4):




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wherein A1, A2, A3 and A4 each represent a carbon atom, a nitrogen atom or an oxidized nitrogen atom;


R1 represents a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group;


G1 and G2 each represent an oxygen atom or a sulfur atom;


X, which may be identical or different each other, represents a hydrogen atom, a halogen atom, an optionally substituted C1-C3 alkyl group or a trifluoromethyl group;


n represents an integer of 0 to 4;


Q1 represents a phenyl group; a substituted phenyl group having one or more substituents, which may be identical or different, selected from a halogen atom, a C1-C4 alkyl group, a 01-04 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4-alkylamino group, a cyano group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group; a heterocyclic group (the heterocyclic group herein represents a pyridyl group, a pyridin-N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrolyl group, a pyrazolyl group or a tetrazolyl group); or a substituted heterocyclic group (which means the same as those described above) having one or more substituents, which may be identical or different, selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4-alkylamino group, a cyano group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group or a phenyl group; and


Hal represents a chlorine atom or a bromine atom.


[10] A process for preparation of the compound represented by Formula (1) as described in [1], wherein the compound represented by Formula (4) as described in [9] is reacted with a compound represented by Formula (5):




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(wherein R2 represents a hydrogen atom, an optionally substituted alkyl group or an optionally substituted C1-C4 alkylcarbonyl group; and

    • Q2 represents an optionally substituted phenyl group, an optionally substituted naphthyl group or an optionally substituted heterocyclic group).


[11] A compound represented by Formula (6):




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wherein A1, A2, A3 and A4 each represented by a carbon atom, a nitrogen atom or an oxidized nitrogen atom;


R1 and R2 each represent a hydrogen atom, a C1-C4 alkyl group or a C1-C4 alkylcarbonyl group;


G2 represents an oxygen atom or a sulfur atom;


X, which may be identical or different, represents a hydrogen atom, a halogen atom, an optionally substituted C1-C3 alkyl group or a trifluoromethyl group;


n represents an integer of 0 to 4;


Q2 is represented either by Formula (2):




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(wherein Y1 and Y5, which may be identical or different, each represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y3 represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y2 and Y4 each represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group);


or by Formula (3):




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(wherein Y6 and Y9, which may be identical or different, each represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group or a cyano group; Y8 represents a C1-C4 haloalkoxy group, a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y7 represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group).


[12] A process for preparation of the compound represented by Formula (1) as described in [1], wherein the compound represented by Formula (6) as described in [11] is reacted with a compound represented by Formula (7):




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(wherein G1 represents an oxygen atom or a sulfur atom; Q1 represents a phenyl group; a substituted phenyl group having one or more substituents, which may be identical or different, selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4-alkylamino group, a cyano group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group; a heterocyclic group (the heterocyclic group herein represents a pyridyl group, a pyridin-N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrolyl group, a pyrazolyl group or a tetrazolyl group); or a substituted heterocyclic group (which means the same as those described above) having one or more substituents, which may be identical or different, selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4-alkylamino group, a cyano group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group or a phenyl group; and


L represents a halogen atom or a hydroxyl group).


[13] A compound represented by Formula (8):




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wherein X1a, X2a, Xaa and X4a each represent a hydrogen atom, a C1-C3 alkyl group, a trifluoromethyl group, a hydroxyl group, an amino group or a halogen atom;


Ra and Rb each represent a fluorine atom or a C1-C4 perfluoroalkyl group;


Rc represents a hydroxyl group, a group —O—Rd (wherein Rd represents a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkylsulfonyl, a C1-C3 haloalkylsulfonyl group, an arylsulfonyl group, a C1-C4 alkylcarbonyl group or a C1-C4 haloalkylcarbonyl group), a chlorine atom, a bromine atom or an iodine atom;


R2a represents a hydrogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C4 alkylcarbonyl group or a C1-C4 haloalkylcarbonyl group;


Y1a and Y5a each represent a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C3 alkylsulfinyl group or a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a cyano group, a hydroxyl group or a halogen atom;


Y2a and Y4a each represent a hydrogen atom, a C1-C4 alkyl group or a halogen atom; and


G2a represents an oxygen atom or a sulfur atom.


[14] A process for preparation of the compound represented by Formula (8) as described in [13], wherein a compound represented by Formula (9):




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(wherein J represents a halogen atom or a hydroxyl group; and X1a, X2a, X3a, X4a and G2a have the same meanings as those described in [13]),


is reacted with a compound represented by Formula (10):




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(wherein R—Rb, Rc, Y1a, Y2a, Y4a, Y5a and R2a have the same meanings as those described in [13]).


[15] A process for preparation of a compound represented by Formula (8b):




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(wherein X1a, X2a, X3a, X4a, G2a, R2a, Y1a, Y2a, Y4a, Y5a, Ra and Rb have the same meanings as those described in [13]; and Rc″ represents a chlorine atom, a bromine atom or an iodide atom);


wherein a compound represented by Formula (8a):




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(wherein X1a, X2a, X3a, X4a, G2a, R2a, Y1a, Y2a, Y4a, Y5a, Ra and Rb have the same meanings as those described in [13]; and Rc′ represents a hydroxyl group or a group —O—Rd (wherein Rd represents a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an arylsulfonyl group, a C1-C4 alkylcarbonyl group or a C1-C4 haloalkylcarbonyl group)),


is reacted with a suitable halogenating agent.


[16] A compound represented by Formula (11):




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wherein X1a, X2a, Xaa and X4a each represent a hydrogen atom, a C1-C3 alkyl group, a trifluoromethyl group, a hydroxyl group, an amino group or a halogen atom;


Ra and Rb each represent a fluorine atom or a C1-C4 perfluoroalkyl group;


Rc represents a hydroxyl group, a group —O—Rd (wherein Rd represents a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an arylsulfonyl group, a C1-C4 alkylcarbonyl group or a C1-C4 haloalkylcarbonyl group), a chlorine atom, a bromine atom or an iodine atom;


R1a and R2a each represent a hydrogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C4 alkylcarbonyl group or a C1-C4 haloalkylcarbonyl group;


Y1a and Y5a each represent a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a cyano group, a hydroxyl group or a halogen atom;


Y2a and Y4a each represent a hydrogen atom, a C1-C4 alkyl group or a halogen atom; and


G2a represents an oxygen atom or a sulfur atom.


[17] A process for preparation of the compound represented by Formula (11) as described in [16]:




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(wherein X1a, X2a, X3a, X4a, Ra, Rb, Rc, R1a, R2a, Y1a, Y2a, Y4a, Y5a and G2a have the same meanings as those described in [16]),


wherein the compound represented by Formula (8) as described in [13] is reacted in the presence of a suitable reducing agent.


[18] A process for preparation of a compound represented by Formula (12):




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wherein X1a, X2a, X3a and X4a each represent a hydrogen atom, a C1-C3 alkyl group, a trifluoromethyl group, a hydroxyl group, an amino group or a halogen atom;


Ra and Rb each represent a fluorine atom or a C1-C4 perfluoroalkyl group;


R1a and R2a each represent a hydrogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C4 alkylcarbonyl group or a C1-C4 haloalkylcarbonyl group;


Y1a and Y5a each represent a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a cyano group, a hydroxyl group or a halogen atom;


Y2a and Y4a each represent a hydrogen atom, a C1-C4 alkyl group or a halogen atom; and


G2a represents an oxygen atom or a sulfur atom.


[19] A process for preparation of a compound represented by Formula (IIb):




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(wherein X1a, X2a, X3a, X4a, G2a, R1a, R2a, Y1a, Y2a, Y4a, Y5a, Ra and Rb have the same meanings as those described in [18]; and Rc″ represents a chlorine atom, a bromine atom or an iodine atom);


wherein a compound represented by Formula (11a):




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(wherein X1a, X2a, X3a, X4a, G2a, R1a, Rea, Y1a, Y2a, Y4a, Y5a, Ra and Rb have the same meanings as those described in [18]; and Rc′ represents a hydroxyl group or a group —O—Rd (wherein Rd represents a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an arylsulfonyl group, a C1-C4 alkylcarbonyl group or a C1-C4 haloalkylcarbonyl group)), is reacted with a suitable halogenating agent.


[20] A compound represented by Formula (13):




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wherein X1a, X2a, X3a and X4a each represent a hydrogen atom, a c1-C3 alkyl group, a trifluoromethyl group, a hydroxyl group, an amino group or a halogen atom;


Ra and Rb each represent a fluorine atom or a C1-04 perfluoroalkyl group;


Rc represents a hydroxyl group, a group —O—Rd (wherein Rd represents a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an arylsulfonyl group, a C1-C4 alkylcarbonyl group or a C1-C4 haloalkylcarbonyl group), a chlorine atom, a bromine atom or an iodine atom;


R1a and R2a each represent a hydrogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C4 alkylcarbonyl group or a C1-C4 haloalkylcarbonyl group;


Y1a and Y5a each represent a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkylthio group, a C1-C4 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a cyano group, a hydroxyl group or a halogen atom;


Y2a and Y4a each represent a hydrogen atom, a C1-C4 alkyl group or a halogen atom;


G1a and G1a each represent an oxygen atom or a sulfur atom;


Q1a represents a phenyl group; a substituted phenyl group having one or more substituents, which may be identical or different, selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4-alkylamino group, a cyano group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group; a heterocyclic group (the heterocyclic group herein represents a pyridyl group, a pyridin-N-oxide group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a thienyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrolyl group, a pyrazolyl group or a tetrazolyl group); or a substituted heterocyclic group (which means the same as those described above) having one or more substituents, which may be identical or different, selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4-alkylamino group, a cyano group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group.


[21] A process for preparation of the compound represented by Formula (13) as described in [20], wherein the compound represented by Formula (11) as described in [16] is reacted with a compound represented by Formula (14):




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(wherein J′ represents a halogen atom or a hydroxyl group; and Q1a and G1a have the same meanings as those described in [20]);


or a compound represented by Formula (15):




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(wherein Q1a and G1a have the same meanings as those described in [20]).


[22] A process for preparation of the compound represented by Formula (13) as described in [20], wherein a compound represented by Formula (16):




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(wherein J″ represents a halogen atom or a hydroxyl group; and X1a, X2a, X3a, X4a, G1a, G2a, R1a and Q1a have the same meanings as those described in [20]),


is reacted with the compound represented by Formula (10) as described in [14].


[23] A process for preparation of a compound represented by Formula (17):




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(wherein X1a, X2a, X3a, X4a, Ra, Rb, R1a, R2a, Y1a, Y2a, Y4a, Y5a, G1a, G2a and Q1a have the same meanings as those described in [20]),


wherein the compound represented by Formula (13) as described in [20] is reacted with a suitable fluorinating agent.


[24] A process for preparation of a compound represented by Formula (13b):




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(wherein X1a, X2a, X3a, X4a, Ra, Rb, R2a, Y1a, Y2a, Y4a, Y5a, G1a, G2a and Q1a have the same meanings as those described in [20]; and Rc″ represents a chlorine atom, a bromine atom or an iodine atom),


wherein a compound represented by Formula (13a):




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(wherein X1a, X2a, X3a, X4a, Re, Rb, R1a, R2a, Y1a, Y2a, Y4a, Y5a, G1a, G2a and Q1a have the same meanings as those described in [20]; and Rc′ represents a hydroxyl group or a group —O—Rd (wherein Rd represents a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, an arylsulfonyl group, a C1-C4 alkylcarbonyl group or a C1-C4 haloalkylcarbonyl group)),


is reacted with a suitable halogenating agent.


[25] An insecticide containing the compound as described in [1] to [8] as the active ingredient.


[26] A horticultural or agricultural insecticide containing the compound as described in [1] to [8] as an active ingredient.


[27] A method of using formulation in treating crops for cultivation or the soil to be treated with an effective amount of the compound as described in [1] to [8], in order to protect the crops from harmful organisms.


[28] A composition in which the compound as described in [1] to [8] is mixed with a suitable inert carrier, and optionally with an auxiliary agent.


[29] A mixture in which the compound as described in [1] to [8] is combined with at least one other insecticide and/or fungicide.


The compound of the present invention exhibits an excellent controlling effect as a pesticide at low doses, and also exhibits an excellent controlling effect when used in combination with a pesticide, an acaricide, a nematocide, a fungicide, a herbicide, a plant growth controlling agent, a biocide or the like.







BEST MODE FOR CARRYING OUT THE INVENTION

The terms used in the formulae described in the present invention, such as Formula (1) have the meanings as described below, respectively.


A “halogen atom” represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.


The expression “Ca-Cb (wherein, a and b represent an integer of 1 or more)” means such that, for example, “C1-C3” means having 1 to 3 carbon atoms, “C2-C6” means having 2 to 6 carbon atoms, and “C1-C4” means having 1 to 4 carbon atoms.


The terms “n-”, “i-”, “s-” and “t-” mean normal-, iso-, secondary- and tertiary-, respectively.


The term “optionally substituted alkyl group” means a straight, branched or cyclic alkyl group substituted with substituents, which may be identical or different, such as a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl group, a C1-C6 alkylcarbonyloxy group, a C1-C6 haloalkylcarbonyloxy group, an amino group, a C1-C6 alkylamino group, a di-C1-C6-alkylamino group, an optionally substituted phenyl group, an optionally substituted phenylcarbonyl group, an optionally substituted phenylamino group and an optionally substituted heterocyclic group.


The term “optionally substituted C1-C4 alkylcarbonyl group” means a straight, branched or cyclic alkylcarbonyl group having 1 to 4 carbon atoms which is substituted with substituents, which may be identical or different, such as a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl group, a C1-C6 alkylcarbonyloxy group, a C1-C6 haloalkylcarbonyloxy group, an amino group, a C1-C6 alkylamino group, a di-C1-C6-alkylamino group, an optionally substituted phenyl group, an optionally substituted phenylcarbonyl group, an optionally substituted phenylamino group and an optionally substituted heterocyclic group.


The term “optionally substituted phenyl group” means a phenyl substituted with substituents, which may be identical or different, such as a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl group, a C1-C6 alkylcarbonyloxy group, a C1-C6 haloalkylcarbonyloxy group, an amino group, a C1-C6 alkylamino group, a di-C1-C6-alkylamino group, an acetylamino group, an optionally substituted phenyl group, an optionally substituted phenylcarbonyl group, an optionally substituted phenylamino group and an optionally substituted heterocyclic group.


The term “optionally substituted naphthyl group” means a naphthyl group substituted with substituents, which may be identical or different, such as a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl group, a C1-C6 alkylcarbonyloxy group, a C1-C6 haloalkylcarbonyloxy group, an amino group, a C1-C6 alkylamino group, a di-C1-C6-alkylamino group, an acetylamino group, an optionally substituted phenyl group, an optionally substituted phenylcarbonyl group, an optionally substituted phenylamino group and an optionally substituted heterocyclic group.


The term “optionally substituted heterocyclic group” means a heterocyclic group substituted with substituents, which may be identical or different, such as a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 haloalkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 haloalkoxycarbonyl group, a C1-C6 alkylcarbonyloxy group, a C1-C6 haloalkylcarbonyloxy group, an amino group, a C1-C6 alkylamino group, a di-C1-C6-alkylamino group, an acetylamino group, an optionally substituted phenyl group, an optionally substituted phenylcarbonyl group, an optionally substituted phenylamino group or an optionally substituted heterocyclic group.


Further, the term “C1-C3 alkyl group” represents a straight or branched alkyl group having 1 to 3 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, cyclopropyl, etc.; the term “C1-C4 alkyl group” represents a straight or branched alkyl group having 1 to 4 carbon atoms such as, for example, n-butyl, s-butyl, i-butyl, t-butyl, etc. in addition to the C1-C3 alkyl group; and the term “C1-C6 alkyl group” represents a straight or branched alkyl group having 1 to 6 carbon atoms, such as n-pentyl, 2-pentyl, 3-pentyl, neopentyl, n-hexyl, 2-hexyl, 4-methyl-2-pentyl, 3-methyl-n-pentyl, etc. in addition to the C1-C4 alkyl group.


The term “C1-C3 haloalkyl group” represents a straight or branched alkyl group having 1 to 3 carbon atoms, substituted with one or more halogen atoms which may be identical or different, such as monofluoromethyl, difluoromethyl, trifluoromethyl, monochioromethyl, dichloromethyl, trichloromethyl, monobromomethyl, dibromomethyl, tribromomethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1-chloroethyl, 2-chloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 1-bromoethyl, 2-bromoethyl, 2,2-dibromoethyl, 2,2,2-tribromoehtyl, 2-iodoethyl, pentafluoroethyl, 3-fluoro-n-propyl, 3-chloro-n-propyl, 3-bromo-n-propyl, 1,3-difluoro-2-propyl, 1,3-dichloro-2-propyl, 1,1,1-trifluoro-2-propyl, 1-chloro-3-fluoro-2-propyl, 1,1,1,3,3,3-hexafluoro-2-propyl, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propyl, 2,2,3,3,3-pentafluoro-n-propyl, heptafluoro-i-propyl or heptafluoro-n-propyl. The term “C1-C4 haloalkyl group” represents a straight or branched alkyl group having 1 to 4 carbon atoms and being substituted with one or more halogen atoms which may be identical or different, such as 4-fluoro-n-butyl, nonafluoro-n-butyl and nonafluoro-2-butyl in addition to the “C1-C3 haloalkyl group”.


The term “C2-C4 alkenyl group” represents an alkenyl group having 2 to 4 carbon atoms and a double bond in the carbon chain, such as vinyl, allyl, 2-butenyl or 3-butenyl. The Term “C2-C4 haloalkenyl group” represents a straight or branched alkenyl group having 2 to 4 carbon atoms and a double bond in the carbon chain, and being substituted with one or more halogen atoms which may be identical or different, such as 3,3-diflouro-2-propenyl, 3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl, 2,3-dibromo-2-propenyl, 4,4-difluoro-3-butenyl and 3,4,4-tribromo-3-butenyl.


The term “C2-C4 alkynyl group” represents a straight or branched alkynyl group having 2 to 4 carbon atoms and a triple bond in the carbon chain, such as propargyl, 1-butyn-3-yl and 1-butyn-3-methyl-3-yl. The term “C2-C4 haloalkynyl group” represents a straight or branched alkenyl group having 2 to 4 carbon atoms and a triple bond in the carbon chain, and being substituted with one or more halogen atoms which may be identical or different.


The term “C3-C6 cycloalkyl group” represents a cycloalkyl group having a ring structure of 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl and cyclohexyl. The term “C3-C6 halocycloalkyl group” represents a cycloalkyl group having a ring structure of 3 to 6 carbon atoms and being substituted with one more halogen atoms which may be identical or different, such as 2,2,3,3-tetrafluorocylcobutyl, 2-chlorocyclohexyl and 4-chlorocyclohexyl.


The term “C1-C3 alkoxy group” represents a straight or branched alkoxy group having 1 to 3 carbon atoms, such as methoxy, ethoxy, n-propyloxy and isopropyloxy. The term “C1-C3 haloalkoxy group” represents a straight or branched haloalkoxy group having 1 to 3 carbon atoms, substituted with one or more halogen atoms which may be identical or different, such as trifluoromethoxy, 1,1,1,3,3,3-hexafluoro-2-propyloxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy and 3-fluoro-n-propyloxy. The term “C1-C4 haloalkoxy group” represents a straight or branched haloalkoxy group having 1 to 4 carbon atoms and being substituted with one or more halogen atoms which may be identical or different, such as 1,1,1,3,3,4,4,4-octafluoro-2-butyloxy in addition to the “C1-C3 haloalkoxy group”.


The term “C1-C3 alkylthio group” represents a straight or branched alkylthio group having 1 to 3 carbon atoms, such as methylthio, ethylthio, n-propylthio, i-propylthio and cyclopropylthio. The term “C1-C4 alkylthio group” represents a straight or branched alkylthio group having 1 to 4 carbon atoms, such as n-butylthio, i-butylthio, s-butylthio, t-butylthio and cyclopropylmethylthio in addition to the “C1-C3 alkylthio group”. The term “C1-C3 haloalkylthio group” represents a straight or branched alkylthio group having 1 to 3 carbon atoms, substituted with one or more halogen atoms which may be identical of different, such as trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, heptafluoro-n-propylthio and heptafluoro-i-propylthio. The term “C1-C4 haloalkylthio group” represents a straight or branched alkylthio group having 1 to 4 carbon atoms and being substituted with one or more halogen atoms which may be identical or different, such as nonafluoro-n-butylthio, nonafluoro-s-butylthio and 4,4,4-trifluoro-n-butylthio in addition to the “C1-C3 haloalkylthio group”.


The term “C1-C3 alkylsulfinyl group” represents a straight or branched alkylsulfinyl group having 1 to 3 carbon atoms, such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl or cyclopropylsulfinyl. The term “C1-C3 haloalkylsulfinyl group” represents a straight or branched alkylsulfinyl group having 1 to 3 carbon atoms, substituted with one or more halogen atoms which may be identical or different, such as trifluoromethylsulfinyl, pentafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, heptafluoro-n-propylsulfinyl and heptafluoro-i-propylsulfinyl.


The term “C1-C3 alkylsulfonyl group” represents a straight or branched alkylsulfonyl group having 1 to 3 carbon atoms, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl and cyclopropylsulfonyl. The “C1-C3 haloalkylsulfonyl group” represents a straight or branched alkylsulfonyl group having 1 to 3 carbon atoms, substituted with one or more halogen atoms which may be identical or different, such as trifluomethylsulfonyl, pentafluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, heptafluoro-n-propylsulfonyl or heptafluoro-i-propylsulfonyl.


The term “arylsulfonyl group” represents an arylsulfonyl group having an aromatic ring of 6 to 14 carbon atoms, such as phenylsulfonyl, p-toluenesulfonyl, 1-naphthylsulfonyl, 2-naphthylsulfonyl, anthrylsulfonyl, phenanthrylsulfonyl and acenaphthylenylsulfonyl.


The term “C1-C4 alkylamino group” represents a straight, branched or cyclic alkylamino group having 1 to 4 carbon atoms, such as methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino and cyclopropylamino. The term “di-C1-C4-alkylamino group” represents an amino group substituted with two straight or branched alkyl group having 1 to 4 carbon atoms which may be identical or different, such as dimethylamino, diethylamino and N-ethyl-N-methylamino.


The term “C1-C4 alkylcarbonyl group” represents a straight, branched or cyclic alkylcarbonyl group having 1 to 4 carbon atoms, such as formyl, acetyl, propionyl, isopropylcarbonyl and cyclopropylcarbonyl.


The term “C1-C4 haloalkylcarbonyl group” represents a straight or branched alkylcarbonyl group having 1 to 4 carbon atoms and being substituted with one or more halogen atoms which may be identical or different, such as fluoroacetyl, difluoroacetyl, trifluoroacetyl, chloroacetyl, dichloroacetyl, trichloroacetyl, bromoacetyl, iodoacetyl, 3,3,3-trifluoropropionyl and 2,2,3,3,3-pentafluoropropionyl.


The term “C1-C4 alkylcarbonyloxy group” represents a straight or branched alkylcarbonyloxy group having 1 to 4 carbon atoms, such as acetoxy and propionyloxy.


The term “C1-C4 alkoxycarbonyl group” represents a straight or branched alkoxycarbonyl group having 1 to 4 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl or isopropyloxycarbonyl.


The term “C1-C4 perfluoroalkyl group” represents a straight or branched alkyl group having 1 to 4 carbon atoms and being completely substituted with fluorine atoms, such as trifluoromethyl, pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-i-propyl, nonafluoro-n-butyl, nonafluoro-2-butyl and nonafluoro-i-butyl. The term “C2-C6 perfluoroakyl group”, represents a straight or branched alkyl group having 2 to 6 carbon atoms and being completely substituted with fluorine atoms, such as pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-i-propyl, nonafluoro-n-butyl, nonafluoro-2-butyl, nonafluoro-i-butyl, perfluoro-n-pentyl and perfluoro-n-hexyl.


The term “C1-C6 perfluoroalkylthio group” represents a straight or branched alkylthio group having 1 to 6 carbon atoms and being completely substituted with fluorine atoms, such as trifluoromethylthio, pentafluoroethylthio, heptafluoro-n-propylthio, heptafluoro-i-propylthio, nonafluoro-n-butylthio, nonafluoro-2-butylthio, nonafluoro-i-butylthio, perfluoro-n-pentylthio and perfluoro-n-hexylthio.


The term “C1-C6 perfluoroalkylsulfinyl group” represents a straight or branched alkylsulfinyl group having 1 to 6 carbon atoms and being completely substituted with fluorine atoms, such as trifluoromethylsulfinyl, pentafluoroethylsulfinyl, heptafluoro-n-propylsulfinyl, heptafluoro-i-propylsulfinyl, nonafluoro-n-butylsulfinyl, nonafluoro-2-butylsulfinyl, nonafluoro-i-butylsulfinyl, perfluoro-n-pentylsulfinyl and perfluoro-n-hexylsulfinyl.


The term “C1-C6 perfluoroalkylsulfonyl group” represents a straight or branched alkylsulfonyl group having 1 to 6 carbon atoms and being completely substituted with fluorine atoms, such as trifluoromethylsulfonyl, pentafluoroethylsulfonyl, heptafluoro-n-propylsulfonyl, heptafluoro-i-propylsulfonyl, nonafluoro-n-butylsulfonyl, nonafluoro-2-butylsulfonyl, nonafluoro-i-butylsulfonyl, perfluoro-n-pentylsulfonyl and perfluoro-n-hexylsulfonyl.


The compound represented by Formula (1) of the invention may comprise one or a plurality of chiral carbon atoms or chiral centers in the structure, and thus two or more optical isomers may exist. The present invention includes all of the individual optical isomers and mixtures comprising them at any proportions. Furthermore, the compound represented by Formula (1) of the invention may exist in the form of two or more stereoisomers originating from carbon-carbon double bonds in the structure, and the invention includes all of the individual stereoisomers and mixtures comprising them at any proportions.


The substituents or atoms preferred as the substituents for the compounds represented by the above-mentioned formulae such as Formula (1) of the invention will be presented below.


A1, A2, A3 and A4 are preferably such that A1 is a carbon atom, a nitrogen atom or an oxidized nitrogen atom and at the same time A2, A3 and A4 are all carbon atoms, and more preferably such that A1, A2, A3 and A4 are all carbon atoms.


R1 is preferably a hydrogen atom or a C1-C4 alkyl group, and more preferably a hydrogen atom, a methyl group or an ethyl group.


R2 is preferably a hydrogen atom or a C1-C4 alkyl group, and more preferably a hydrogen atom, a methyl group or an ethyl group.


G1 and G2 are each preferably an oxygen atom or a sulfur atom, and more preferably G1 and G2 are both an oxygen atom.


X is preferably a hydrogen atom or a halogen atom, and more preferably a hydrogen atom or a fluorine atom.


n is preferably 0, 1 or 2, and more preferably 0 or 1.


X1 is preferably a hydrogen atom or a halogen atom, and more preferably a hydrogen atom or a fluorine atom.


X2 is preferably a hydrogen atom or a fluorine atom, and more preferably a hydrogen atom.


X3 and X4 are preferably a hydrogen atom.


Q1 is preferably a phenyl group; a phenyl group optionally substituted with one or more substituents, which may be identical or different, selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4-alkylamino group, a cyano group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group and an acetylamino group; a pyridyl group; or a pyridyl group optionally substituted with one or more substituents, which may be identical or different, selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4-alkylamino group, a cyano group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group and an acetylamino group.


More preferably, Q1 is a phenyl group; a phenyl group having 1 to 3 substituents, which may be identical or different, selected from a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, a trifluoromethyl group, a methoxy group, a trifluoromethoxy group, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a methylamino group, a dimethylamino group, a cyano group and a nitro group; a pyridyl group; or a pyridyl group having 1 or 2 substituents, which may be identical or different, selected from a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, a trifluoromethyl group, a methoxy group, a trifluoromethoxy group, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a methylamino group, a dimethylamino group, a cyano group and a nitro group.


Q2 is preferably a substituted phenyl group represented by Formula (2) or a substituted pyridyl group represented by Formula (3), wherein:


Y1 and Y5 are each preferably a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a 2-butyl group, a trifluoromethyl group, a methylthio group, a methylsulfinyl group, a methylsufonyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group and a cyano group;


Y6 and Y9 are each preferably a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a 2-butyl group, a trifluoromethyl group, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group and a cyano group;


Y2, Y4 and Y7 are each preferably a hydrogen atom, a halogen atom or a methyl group, and more preferably a hydrogen atom;


Y3 is preferably a pentafluoroethyl group, a heptafluoro-n-propyl group, a heptafluoro-i-propyl group, a nonafluoro-n-butyl group, a nonafluoro-2-butyl group, a nonafluoro-i-butyl group, a trifluoromethylthio group, a pentafluoroethylthio group, a heptafluoro-n-propylthio group, a heptafluoro-i-propylthio group, a nonafluoro-n-butylthio group, a nonafluoro-2-butylthio group, a trifluoromethylsulfinyl group, a pentafluoroethylsulfinyl group, a heptafluoro-n-propylsulfinyl group, a heptafluoro-i-propylsulfinyl group, a nonafluoro-n-butylsulfinyl group, a nonafluoro-2-butylsulfinyl group, a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group, a heptafluoro-n-propylsulfonyl group, a heptafluoro-i-propylsulfonyl group, a nonafluoro-n-butylsulfonyl group or anonafluoro-2-butylsulfonyl group;


Y8 is preferably a pentafluoroethyl group, a heptafluoro-n-propyl group, a heptafluoro-i-propyl group, a nonafluoro-n-butyl group, a nonafluoro-2-butyl group, a nonafluoro-i-butyl group, a trifluoromethylthio group, a pentafluoroethylthio group, a heptafluoro-n-propylthio group, a heptafluoro-i-propylthio group, a nonafluoro-n-butylthio group, a nonafluoro-2-butylthio group, a trifluoromethylsulfinyl group, a pentafluoroethylsulfinyl group, a heptafluoro-n-propylsulfinyl group, a heptafluoro-i-propylsulfinyl group, a nonafluoro-n-butylsulfinyl group, a nonafluoro-2-butylsulfinyl group, a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group, a heptafluoro-n-propylsulfonyl group, a heptafluoro-i-propylsulfonyl group, a nonafluoro-n-butylsulfonyl group, a nonafluoro-2-butylsulfonyl group, a pentafluoroethoxy group and a 1,1,1,3,3,3-hexafluoro-i-propyloxy group.


L is preferably a chlorine atom, a bromine atom or a hydroxyl group.


R1a is preferably a hydrogen atom or a C1-C4 alkyl group, and more preferably a hydrogen atom, a methyl group or an ethyl group.


R2a is preferably a hydrogen atom or a C1-C4 alkyl group, and more preferably a hydrogen atom, a methyl group or an ethyl group.


G1a and G2a are each preferably an oxygen atom or a sulfur atom, and more preferably G1a and G2a are both an oxygen atom.


X1a is preferably a hydrogen atom or a halogen atom, and more preferably a hydrogen atom or a fluorine atom.


X2a is preferably a hydrogen atom or a fluorine atom, and more preferably a hydrogen atom.


X3a and X4a are preferably a hydrogen atom.


Y1a and Y5a are each preferably a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a 2-butyl group, a trifluoromethyl group, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group or a cyano group.


Y2a and Y4a are each preferably a hydrogen atom, a halogen atom and a methyl group, and more preferably a hydrogen atom.


Q1a is preferably a phenyl group; a phenyl group optionally substituted with one or more substituents, which may be identical or different, selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4-alkylamino group, a cyano group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group and an acetylamino group; a pyridyl group; or a pyridyl group optionally substituted with one or more substituents, which may be identical or different, selected from a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl group, a C3-C6 cycloalkyl group, a c3-C6 halocycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1-C3 alkylsulfonyl group, a C1-C3 haloalkylsulfonyl group, a C1-C4 alkylamino group, a di-C1-C4-alkylamino group, a cyano group, a nitro group, a hydroxyl group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxygroup, a C1-C4 alkoxycarbonyl group and an acetylamino group.


More preferably, Q1a is a phenyl group; a phenyl group having 1 to 3 substituents, which may be identical or different, selected from a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, a trifluoromethyl group, a methoxy group, a trifluoromethoxy group, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a methylamino group, a dimethylamino group, a cyano group and a nitro group; a pyridyl group; or a pyridyl group having 1 or 2 substituents, which may be identical or different, selected from a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, a trifluoromethyl group, a methoxy group, a trifluoromethoxy group, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a methylamino group, a dimethylamino group, a cyano group and a nitro group.


Ra and Rb are each preferably a fluorine atom, a trifluoromethyl group, a pentafluoroethyl group or a heptafluoro-n-propyl group, and more preferably a fluorine atom, a trifluoromethyl group or a pentafluoroethyl group.


Rc is preferably a hydroxyl group, a chlorine atom, a bromine atom, an iodine atom, a methoxy group, an ethoxy group, a methylsulfonyloxy group, a trifluoromethylsulfonyloxy group, a phenylsulfonyloxy group, a p-toluenesulfonyloxy group, an acetoxy group or a trifluoroacetoxy group, and more preferably a hydroxyl group, a chlorine atom, a bromine atom, a methoxy group, a methylsulfonyloxy group, a trifluoromethylsulfonyloxy group, a phenylsulfonyloxy group or a p-toluenesulfonyloxy group, and even more preferably a hydroxyl group, a chlorine atom or a bromine atom.


Rc′ is preferably a hydroxyl group.


Rc″ is preferably a chlorine atom or a bromine atom.


J, J′ and J″ are each preferably a hydroxyl group, a chlorine atom or a bromine atom, and more preferably a chlorine atom.


Representative processes for preparation of the compound of the invention will be described in the following. Preparation of the compound of the invention is possible by following the procedure, but the preparation route is not limited only to the process for preparation described below.


With regard to the formulae prepared by the following processes for preparation, X1, X2, X3, X4, Y1, Y2, Y4, Y5, G1, G2, R1, R2 and Q1 may correspond to X1a, X2a, Xaa, X4a, Y1a, Y2a, Y4a, Y5a, G1a, G2a, R1a, R2a and Q1a, respectively, and it is also possible vice versa. Further, Q2 has the meaning as described in claim 1 or is represented by Formula (2):




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(wherein Y1, Y2, Y3, Y4 and Y5 have the same meanings as described above),


by Formula (3):




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(wherein Y6, Y7, Y8 and Y9 have the same meanings as described above),


or by Formula (18):




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(wherein Y1a, Y2a, Y4a, Y5a, Ra, Rb and Rc have the same meaning as described above).


Preparation Process 1




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wherein A1, A2, A3, A4, G1, G2, R1, R2, X, n, Q1 and Q2 have the same meaning as described above, and L represents a functionality capable of leaving such as a halogen atom or a hydroxyl group.


1-(i) Formula (19)+Formula (20)→Formula (21)


An aromatic carboxamide derivative having a nitro group represented by Formula (21) can be prepared by reacting an m-nitro aromatic carboxylic acid derivative having a leaving group represented by Formula (19) with an aromatic amine derivative represented by Formula (20) in a suitable solvent or without a solvent. In this step, an appropriate base can be also used.


For the solvent, use can be made of any solvent which does not impede the reaction significantly, for example, water; aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as dichloromethane, chloroform and tetrachlorocarbon; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; alcohols such as methanol and ethanol; ketones such as acetone, methyl isobutyl ketone and cyclohexanone; amides such as dimethyl formamide and dimethyl acetamide; nitriles such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidazolidinone, which may be used alone or in combination of two or more.


Further, for the base, use can be made of organic bases such as triethylamine, tri-n-butylamine, pyridine and 4-dimethyl aminopyridine; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; carbonates such as sodium hydrogen carbonate and potassium carbonate; phosphates such as dipotassium hydrogen phosphate and trisodium phosphate; alkali metal hydrides such as sodium hydride; and alkali metal alcoholates such as sodium methoxide and sodium ethoxide. These bases may be appropriately used in a quantity of 0.01 to 5-fold molar equivalents with respect to the compound represented by Formula (19).


The reaction temperature may be suitably selected within the range of −20° C. to the reflux temperature of the solvent used, and the reaction time within the range of several minutes to 96 hours.


Among the compounds represented by Formula (19), an aromatic carboxylic acid halide derivative may be prepared easily from an aromatic carboxylic acid by a conventional process using a halogenating agent. A halogenating agent may be, for example, thionyl chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride, phosphorus trichloride and the like.


Meanwhile, it is possible to prepare the compound represented by Formula (21) from an m-nitro aromatic carboxylic acid derivative and the compound represented by Formula (20) without using a halogenating agent. The process is described in, for example, Chem. Ber. p. 788 (1970), in which a condensing agent comprising N,N′-dicyclohexylcarbodiimide is used, suitably with an additive such as 1-hydroxybenzotriazole. Other condensing agents that can be used in this case may include 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, 1,1′-carbonylbis-1H-imidazole and the like.


Furthermore, for other processes for preparation of the compounds represented by Formula (21), there can be used a mixed acid anhydride process using chloroformic acid esters or a process described in J. Am. Chem. Soc., p. 5012 (1967) in order to prepare the compound represented by Formula (21). The chloroformic acid esters used in this case may include isobutyl chloroformate, isopropyl chloroformate and the like. In addition to chloroformic acid esters, diethylacetyl chloride, trimethylacetyl chloride and the like can also be used.


Both the process using a condensing agent and the mixed acid anhydride process are not limited by the solvent, the reaction temperature and the reaction time as described in the references above. An inert solvent may be used which does not impede the reaction significantly, and the reaction temperature and the reaction time may also be selected appropriately in accordance with the proceeding of the reaction.


1-(ii) Formula (21)→Formula (22)


An aromatic carboxamide derivative having an amino group represented by Formula (22) can be derived from the aromatic carboxamide derivative having a nitro group represented by Formula (21) by means of reduction. Such reduction is illustrated by a process using hydrogenation and a process using a metal compound (for example, tin (II) chloride (anhydride), iron powder, zinc powder and the like).


The reaction of the former process can be carried out in a suitable solvent in the presence of catalyst at atmospheric pressure or a higher pressure under a hydrogen atmosphere. Examples of the catalyst may include palladium catalysts such as palladium-carbon, nickel catalysts such as Raney nickel, cobalt catalysts, ruthenium catalysts, rhodium catalysts, platinum catalysts and the like, and examples of the solvent may include water; alcohols such as methanol and ethanol; aromatic hydrocarbons such as benzene, toluene; chained or cyclic ethers such as ether, dioxane, tetrahydrofuran, etc.; and esters such as ethyl acetate. The compound of Formula (22) can be efficiently prepared by appropriately selecting the pressure within a range of 0.1 to 10 Mpa, the reaction temperature within a range of −20° C. to the reflux temperature of the solvent used, and the reaction time within a range of several minutes to 96 hours.


For the latter process, there can be used a method using tin (II) chloride (anhydride) as a metal compound under the conditions described in “Organic Syntheses” Coll. Vol. III, P. 453.


1-(iii) Formula (22)+Formula (23)→Formula (24)


A compound of the invention represented by Formula (24) can be prepared by reacting the aromatic carboxamide derivative having an amino group represented by Formula (22) with the compound represented by Formula (23) in a suitable solvent. In this step, a suitable base can also be used.


For the solvent, use can be made of any solvent which does not impede the reaction significantly, for example, water; aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as dichloromethane, chloroform and tetrachlorocarbon; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; alcohols such as methanol and ethanol; ketones such as acetone, methyl isobutyl ketone and cyclohexanone; amides such as dimethyl formamide and dimethyl acetamide; nitriles such as acetonitrile; and inert solvents such as 1,3-dimethyl-2-imidazolidinone, which may be used alone or in combination of two or more.


Further, for the base, use can be made of organic bases such as triethylamine, tri-n-butylamine, pyridine and 4-dimethyl aminopyridine; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; carbonates such as sodium hydrogen carbonate and potassium carbonate; phosphates such as dipotassium hydrogen phosphate and trisodium phosphate; alkali metal hydrides such as sodium hydride; and alkali metal alcoholates such as sodium methoxide and sodium ethoxide. Such base may be appropriately used in a quantity of 0.01 to 5-fold molar equivalents with respect to the compound represented by Formula (22). The reaction temperature may be suitably selected within the range of −20° C. to the reflux temperature of the solvent used, and the reaction time within the range of several minutes to 96 hours. It is also possible to prepare by the method using a condensing agent as described in 1-(i) or the mixed acid anhydride method.


1-(iv) Formula (24)+Formula (25)→Formula (26)


A compound represented by Formula (26) of the invention can be prepared by reacting a compound represented by Formula (24) with an alkyl compound having a leaving group represented by Formula (25) in a solvent or without a solvent. The compound represented by Formula (25) may include an alkyl halide such as methyl iodide, ethyl iodide or n-propyl bromide. Further, in this step, it is possible to use a suitable base or a solvent, and for such base or solvent, those exemplified in 1-(i) may be used. The reaction temperature, the reaction time and the like may be selected according to the examples as given in 1-(i).


Alternatively, it is also possible to prepare the compound represented by Formula (26) by reacting the compound represented by Formula (24) with an alkylating agent such as dimethyl sulfate, diethyl sulfate and the like, instead of the compound represented by Formula (25).


Preparation Process 2




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wherein A1, A2, A3, A4, G1, G2, R1, R2, X, n, Q1, Q2, L and Hal have the same meaning as those described in the above.


2-(i) Formula (27)+Formula (23)→Formula (28)


Carboxylic acids having an acylamino group represented by Formula (28) can be prepared by reacting carboxylic acids having an amino group represented by Formula (27) as starting material with the compound represented by Formula (23) according to the conditions described in 1-(i).


2-(ii) Formula (28)→Formula (29)


A compound represented by Formula (29) can be prepared by a known conventional method in which the compound represented by Formula (28) is reacted with thionyl chloride, oxalyl chloride, phosgene, phosphorus oxychloride, phosphorus pentachloride, phosphorus trichloride, thionyl bromide, phosphorus tribromide, diethylaminosulfur trifluoride and the like.


2-(iii) Formula (29)+Formula (20)→Formula (30)


A compound represented by Formula (30) can be prepared by reacting the compound represented by Formula (29) with a compound represented by. Formula (20) according to the conditions described in 1-(i).


2-(iv) Formula (28)+Formula (20)→Formula (30)


The compound represented by Formula (30) can be also prepared by reacting the compound represented by Formula (28) with the compound represented by Formula (20) according to the conditions of using a condensing agent as described in 1-(i) or the conditions of using the mixed acid anhydride method.


Preparation Process 3




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wherein A1, A2, A3, A4, G1, R1, R2, X, n, Q1, Q2 and L have the same meaning as those described in the above.


3-(i) Formula (31)→Formula (32)


A compound represented by Formula (32) can be prepared by reacting a compound represented by Formula (31) with the Lawesson's reagent according to the known conditions as described in Synthesis, p. 463 (1993) or in Synthesis, p. 829 (1984). Conditions such as a solvent, a reaction temperature and the like are not limited to those as described in the literature.


3-(ii) Formula (32)+Formula (23)→Formula (33)


A compound represented by Formula (33) can be prepared by reacting the compound represented by Formula (32) with the compound represented by Formula (23) according to the conditions as described in 1-(i).


Preparation Process 4




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wherein A1, A2, A3, A4, R1, R2, X, n, Q1 and Q2 have the same meaning as those described in the above.


A compound represented by Formula (35) and a compound represented by Formula (36) can be prepared from the compound represented by Formula (34) according to the conditions as described in 3-(i). Conditions such as a solvent, a reaction temperature and the like are not limited to those as described in the literature. These two compounds can be easily separated and purified by means of a known separation and purification technique such as silica gel column chromatography.


Preparation Process 5




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wherein A1, A2, A3, A4, G1, G2, R1, R2, X, n, Q1, Q2 and L have the same meaning as those described in the above.


5-(i) Formula (37)→Formula (38)


A compound represented by Formula (38) can be prepared by carrying out an amination reaction using ammonia according to the conditions as described in, for example, J. Org. Chem., p. 280 (1958). Conditions such as a reaction solvent are not limited to those as described in the literature, and any inert solvent which does not impede the reaction significantly may be used. A reaction temperature and a reaction time may also be selected in accordance with the proceeding of the reaction. Further, it is also possible to use methylamine, ethylamine and the like, in addition to ammonia, as the aminating agent.


5-(ii) Formula (38)+Formula (23)→Formula (39)


A compound represented by Formula (39) can be prepared by reacting the compound represented by Formula (38) with a compound represented by Formula (23) according to the conditions as described in 1-(i).


Preparation Process 6




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wherein R2 has the same meaning as described in the above; Y1 and Y5 each represent a methyl group, a chlorine atom, a bromine atom or an iodine atom; Y2 and Y4 have the same meaning as those described in the above; Rf represents a C1-C6 perfluoroalkyl group; and m represents 1 or 2.


6-(i) Formula (40)+Formula (41)→Formula (42)


A compound represented by Formula (42) can be prepared by reacting an aminothiophenol represented by Formula (40) with a haloalkyl iodide represented by Formula (41) according to the method as described in J. Fluorine Chem., p. 207 (1994).


The haloalkyl iodide represented by Formula (41) may include, for example, trifluoromethyl iodide, pentafluoroethyl iodide, heptafluoro-n-propyl iodide, heptafluoroisopropyl iodide, nonafluoro-n-butyl iodide, nonafluoro-2-butyl iodide and the like, and these compounds represented by Formula (40) may be suitably used in the range of 1 to 10-fold molar equivalents.


The solvent used in this step is not limited to those solvents as described in the above literature, and the solvent may be any of those not impeding the reaction significantly, for example, water; aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as dichloromethane, chloroform and tetrachlorocarbon; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; alcohols such as methanol and ethanol; ketones such as acetone, methyl isobutyl ketone and cyclohexanone; amides such as dimethyl formamide and dimethylacetamide; nitriles such as acetonitrile; or inert solvents such as 1,3-dimethyl-2-imidazolidinone, hexamethylphosphate triamide and the like, which may used alone or in combination of two or more. A polar solvent is particularly preferred. The reaction temperature may be suitably selected within the range of −20° C. to the reflux temperature of the solvent used, and the reaction time within the range of several minutes to 96 hours.


6-(ii) Formula (42)→Formula (43)


A compound represented by Formula (43) can be prepared using a suitable halogenating agent, for example, according to the method as described in Synth. Commun., p. 1261 (1989).


The halogenating agent may include, for example, chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide and the like, and these compounds represented by Formula (42) may be suitably used in the range of 1 to 10-fold molar equivalents.


In this step, it is possible to use a suitable solvent. Such solvent for use is not limited to the solvents as described in the above literature, and the solvent may be any of those not impeding the reaction significantly, for example, water; aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as dichloromethane, chloroform and tetrachlorocarbon; chained or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane; esters such as ethyl acetate and butyl acetate; alcohols such as methanol and ethanol; ketones such as acetone, methyl isobutyl ketone and cyclohexanone; amides such as dimethyl formamide and dimethylacetamide; nitriles such as acetonitrile; or inert solvents such as 1,3-dimethyl-2-imidazolidinone, hexamethylphosphate triamide and the like, which may used alone or in combination of two or more. A polar solvent is particularly preferred. The reaction temperature may be suitably selected within the range of −20° C. to the reflux temperature of the solvent used, and the reaction time within the range of several minutes to 96 hours.


6-(iii) Formula (43)→Formula (44) A compound represented by Formula (44) can be prepared using a suitable oxidizing agent, for example, according to the method as described in Tetrahedron Lett., p. 4955 (1994).


The oxidizing agent may include, for example, an organic peracid such as m-chloroperbenzoic acid, sodium meta-periodate, hydrogen peroxide, ozone, selenium dioxide, chromic acid, dinitrogen tetraoxide, acyl nitrate, iodine, bromine, N-bromosuccinimide, iodosyl benzyl, t-butyl hypochlorite and the like.


The solvent used in this step is not limited to the solvents described in the above literature, and the solvent may be any of those not impeding the reaction of the invention significantly. The solvent can be used alone or in combination of two or more. A polar solvent is particularly preferred. The reaction temperature may be suitably selected within the range of −20° C. to the reflux temperature of the solvent used, and the reaction time within the range of several minutes to 96 hours.


6-(iv) Formula (43)→Formula (43-2)


A compound represented by Formula (43-2), wherein either of Y1 and Y5 essentially represents a methyl group, can be prepared from the compound represented by Formula (43) using a suitable methylating agent. In this step, for example, the process described in Tetrahedron Lett., p. 6237 (2000) can be carried out.


6-(v) Formula (43-2)→Formula (44-2)


A compound represented by Formula (44-2), wherein either of Y1 and Y5 essentially represents a methyl group, can be prepared according to the process described in 6-(iii).


Further, the compound of the present invention can be prepared using the aniline derivatives represented by Formula (43), Formula (44), Formula (43-2) and Formula (44-2), by selecting a suitable production process as described in the invention.


Preparation Process 7




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wherein R2, Y1, Y2, Y4, Y5, Rf and m have the same meaning as those described in Preparation Process 6.


The aniline derivative represented by Formula (47) can be prepared according to Preparation Process 6 using a compound represented by Formula (45) as starting material, and further the compound of the invention can be prepared by selecting a suitable production process as described in the invention.


Preparation Process 8




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wherein A1, A2, A3, A4, X, n, G2, R2 and Q2 have the same meaning as those described above.


A compound represented by Formula (49) can be prepared by reacting a compound represented by Formula (48) with a suitable reacting agent in a suitable solvent using a suitable base.


For the solvent, it may be any of those which do not impede the reaction significantly, for example, aliphatic hydrocarbons such as hexane, cyclohexane and methylcyclohexane; aromatic hydrocarbons such as benzene, xylene and toluene; halogenated hydrocarbons such as dichloromethane, chloroform, tetrachlorocarbon and 1,2-dichloroethane; ethers such as diethyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane; amides such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile and propionitrile; ketones such as acetone, methyl isobutyl ketone, cyclohexanone and methyl ethyl ketone; esters such as ethyl acetate and butyl acetate; alcohols such as methanol and ethanol; 1,3-dimehtyl-2-imidazolidinone, sulfolane, dimethylsulfoxide, water and the like, which can be used alone or in combination of two or more.


For the base, use can be made of, for example, organic bases such as triethylamine, tributylamine, pyridine, 4-dimethylaminopyridine; an alkali metal hydroxide such as sodium hydroxide and potassium hydroxide; a carbonate such as sodium hydrogen carbonate and potassium carbonate; a phosphate such as potassium monohydrogen phosphate, trisodium phosphate; an alkali metal hydride such as sodium hydride; an alkali metal alkoxide such as sodium methoxide, sodium ethoxide; an organic lithium such as n-butyllithium; a Grignard reagent such as ethylmagnesium bromide; and the like.


Such base can be appropriately selected or used as solvent, in the range of 0.01 to 5-fold molar equivalents with respect to the compound represented by Formula (48).


For the reacting agent, use can be made of, for example, an alkyl halide such as methyl iodide, ethyl bromide, trifluoromethyl iodide, 2,2,2-trifluoroethyl iodide; an aryl halide such as aryl iodide; a propargyl halide such as propargyl bromide; an acyl halide such as acetyl chloride; an acid anhydride such as trifluoroacetic acid anhydride; an alkyl sulfate such as dimethyl sulfate, diethyl sulfate; and the like.


Such reacting agent can be appropriately selected or used as solvent, in the range of 1 to 5-fold molar equivalents with respect to the compound represented by Formula (48).


The reaction temperature may be appropriately selected in the range from −80° C. to the reflux temperature of the solvent used, and the reaction time in the range from several minutes to 96 hours.


Preparation Process 9




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wherein A1, A2, A3, A4, X, n, G2, R1, R2 and Q2 have the same meaning as those described above.


9-(i) Formula (22)→Formula (50)


A compound represented by Formula (50) can be prepared by reacting a compound represented by Formula (22) with aldehydes or ketones in a suitable solvent, and reacting under a hydrogen atmosphere in the presence of a suitable catalyst.


The solvent may be any of those which do not impede the reaction significantly, for example, aliphatic hydrocarbons such as hexane, cyclohexane and methylcyclohexane; aromatic hydrocarbons such as benzene, xylene and toluene; halogenated hydrocarbons such as dichloromethane, chloroform, tetrachlorocarbon and 1,2-dichloroethane; ethers such as diethyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane; amides such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile and propionitrile; ketones such as acetone, methyl isobutyl ketone, cyclohexanone and methyl ethyl ketone; esters such as ethyl acetate and butyl acetate; alcohols such as methanol and ethanol; 1,3-dimehtyl-2-imidazolidinone, sulfolane, dimethylsulfoxide, water and the like, which can be used alone or in combination of two or more.


Examples of the catalyst may include palladium-based catalysts such as palladium-carbon, palladium hydroxide-carbon; nickel-based catalysts such as Raney nickel; cobalt catalysts, platinum catalysts, ruthenium catalysts, rhodium catalysts and the like.


Examples of the aldehydes may include, for example, formaldehyde, acetaldehyde, propionaldehyde, trifluoroacetaldehyde, difluoroacetaldehyde, fluoroacetaldehyde, chloroacetaldehyde, dichloroacetaldehyde, trichloroacetaldehyde, bromoacetaldehyde and the like.


Examples of the ketones may include, for example, acetone, perfluoroacetone, methyl ethyl ketone and the like.


The reaction pressure may be appropriately selected in the range of 1 atm to 100 atm.


The reaction temperature may be appropriately selected in the range from −20° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately selected in the range from several minutes to 96 hours.


9-(ii) Formula (22)→Formula (50) (Alternative process 1)


The compound represented by Formula (50) can be prepared by reacting the compound represented by Formula (22) with an aldehyde or a ketone in a suitable solvent, and treating the product with a suitable reducing agent.


The solvent may be any of those which do not impede the reaction significantly, for example, aliphatic hydrocarbons such as hexane, cyclohexane and methylcyclohexane; aromatic hydrocarbons such as benzene, xylene and toluene; halogenated hydrocarbons such as dichloromethane, chloroform, tetrachlorocarbon and 1,2-dichloroethane; ethers such as diethyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane; amides such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile and propionitrile; ketones such as acetone, methyl isobutyl ketone, cyclohexanone and methyl ethyl ketone; esters such as ethyl acetate and butyl acetate; alcohols such as methanol and ethanol; 1,3-dimehtyl-2-imidazolidinone, sulfolane, dimethylsulfoxide, water and the like, which can be used alone or in combination of two or more.


Examples of the reducing agent may include, for example, borohydrides such as sodium borohydride, sodium cyanoborohydride, sodium triacetate borohydride and the like.


Examples of the aldehydes may include, for example, formaldehyde, acetaldehyde, propionaldehyde, trifluoroacetaldehyde, difluoroacetaldehyde, fluoroacetaldehyde, chloroacetaldehyde, dichloroacetaldehyde, trichloroacetaldehyde, bromoacetaldehyde and the like.


Examples of the ketones may include, for example, acetone, perfluoroacetone, methyl ethyl ketone and the like.


The reaction temperature may be appropriately selected in the range from −20° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately selected in the range from several minutes to 96 hours.


9-(iii) Formula (22)→Formula (50) (Alternative process 2)


The compound represented by Formula (50), wherein R1 is methyl, can be prepared by reacting the compound represented by Formula (22) with a formylating agent in a suitable solvent or without solvent, and treating the product with a suitable reducing agent.


The solvent may be any of those which do not impede the reaction significantly, for example, aliphatic hydrocarbons such as hexane, cyclohexane and methylcyclohexane; aromatic hydrocarbons such as benzene, xylene and toluene; halogenated hydrocarbons such as dichloromethane, chloroform, tetrachlorocarbon and 1,2-dichloroethane; ethers such as diethyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane; amides such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile and propionitrile; ketones such as acetone, methyl isobutyl ketone, cyclohexanone and methyl ethyl ketone; esters such as ethyl acetate and butyl acetate; alcohols such as methanol and ethanol; 1,3-dimehtyl-2-imidazolidinone, sulfolane, dimethylsulfoxide, water and the like, which can be used alone or in combination of two or more.


Examples of the formylating agent may include, for example, formaldehyde, formic acid, fluoroformic acid, formic acid anhydrides such as formyl(2,2-dimethylpropioic acid), formic acid esters such as phenyl formate, pentafluorobenzaldehyde, oxazole and the like.


Examples of the reducing agent may include, for example, inorganic acids such as sulfuric acid, organic acids such as formic acid, borohydrides such as sodium borohydride and sodium cyanoborohydride, boronic acid, lithium aluminum hydride and the like.


The reaction temperature may be appropriately selected in the range from −20° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately selected in the range from several minutes to 96 hours.


Preparation Process 10




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wherein X1a, X2a, Xaa, X4a, Y1a, Y2a, Y4a, Y5a, G1a, Rea, Ra and Rb have the same meaning as those described above; Rc′ in Formula (51) represents a hydroxyl group or a group —O—Rd (wherein Rd has the same meaning as described above); and Rc″ in Formula (52) represents a chlorine atom, a bromine atom or an iodine atom.


A chlorine compound (or a bromine compound, an iodine compound) represented by Formula (52) can be prepared by reacting a compound represented by Formula (51) with a suitable halogenating agent in a suitable solvent or without a solvent. In this step, a suitable additive may also be used.


The solvent may be any of those which do not impede the reaction significantly, for example, aliphatic hydrocarbons such as hexane, cyclohexane and methylcyclohexane; aromatic hydrocarbons such as benzene, xylene and toluene; halogenated hydrocarbons such as dichloromethane, chloroform, tetrachlorocarbon and 1,2-dichloroethane; ethers such as diethyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane; amides such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile and propionitrile; ketones such as acetone, methyl isobutyl ketone and cyclohexanone; esters such as ethyl acetate and butyl acetate; alcohols such as methanol and ethanol; 1,3-dimehtyl-2-imidazolidinone, sulfolane, dimethylsulfoxide, water and the like, which can be used alone or in combination of two or more.


Examples of the halogenating agent may include, for example, thionyl chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride, phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, a Rydon's reagent, sulfonyl halides such as methanesulfonyl chloride, p-toluenesulfonyl chloride and benzenesulfonyl chloride, sulfonium halide, a sulfonic acid ester, chlorine, bromine, iodine, hypohalogenic acid ester, N-halogenoamine, hydrogen chloride, hydrogen bromide, sodium bromide, potassium bromide, cyanuric chloride, 1,3-dichloro-1,2,4-triazole, titanium(IV) chloride, vanadium(IV) chloride, arsenic(III) chloride, N,N-diethyl-1,2,2-trichlorovinylamine, trichloroacetonitrile, sodium chloride, ammonium bromide, N,N-dimethylchloroforminium chloride, N,N-dimethylchloroforminium bromide, phosphorus trichloride, phosphorus tribromide, N,N-dimethylphosphoamidine dichloride and the like.


An additive may include, for example, metal salts such as zinc chloride, lithium bromide and the like, phase-transfer catalysts, organic bases such as hexamethyl phosphoric acid triamide, inorganic acids such as sulfuric acid, N,N-dimethyl formamide and the like.


Such halogenating agent may be appropriately selected or used as solvent, in the range of 0.01 to 10-fold molar equivalents with respect to the compound represented by Formula (1).


The reaction temperature may be appropriately selected in the range from −80° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately selected in the range from several minutes to 96 hours.


Preparation Process 11




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wherein X1a, X2a, Xaa, X4a, Y1a, Y2a, Y4a, Y5a, G2a, R1a, R2a, Ra, Rb and Rc have the same meaning as those described above.


A compound represented by Formula (54) can be prepared by reacting a compound represented by Formula (53) with a suitable fluorinating agent in a suitable solvent or without a solvent.


The solvent may be any of those which do not impede the reaction significantly, for example, aliphatic hydrocarbons such as hexane, cyclohexane and methylcyclohexane; aromatic hydrocarbons such as benzene, xylene and toluene; halogenated hydrocarbons such as dichloromethane, chloroform, tetrachlorocarbon and 1,2-dichloroethane; ethers such as diethyl ether, dioxane, tetrahydrofuran and 1,2-dimethoxyethane; amides such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile and propionitrile; ketones such as acetone, methyl isobutyl ketone, cyclohexanone and methyl ethyl ketone; esters such as ethyl acetate and butyl acetate; alcohols such as methanol and ethanol; 1,3-dimehtyl-2-imidazolidinone, sulfolane, dimethylsulfoxide, water and the like, which can be used alone or in combination of two or more.


Examples of the fluorinating agent may include 1,1,2,2-tetrafluoroethyl diethylamine, 2-chloro-1,1,2-trifluoroethyl diethylamine, trifluorodiphenylphospholane, difluorotriphenylphospholane, fluoroformic acid esters, sulfur tetrafluoride, potassium fluoride, potassium hydrogen fluoride, cesium fluoride, rubidium fluoride, sodium fluoride, lithium fluoride, antimony(III) fluoride, antimony(V) fluoride, zinc fluoride, cobalt fluoride, lead fluoride, copper fluoride, mercury(II) fluoride, silver fluoride, silver fluoroborate, thallium(I) fluoride, molybdenum(VI) fluoride, arsenic(III) fluoride, bromine fluoride, selenium tetrafluoride, tris(dimethylamino)sulfonium difluorotrimethylsilicate, sodium hexafluorosilicate, quaternary ammonium fluorides, (2-chloroethyl) diethylamine, diethylaminosulfur trifluoride, morpholinosulfur trifluoride, silicon tetrafluoride, hydrogen fluoride, hydrofluoric acid, hydrogen fluoride-pyridine complex, hydrogen fluoride-triethylamine complex, hydrogen fluoride salts, bis(2-methoxyethyl)amino sulfurtrifluoride, 2,2-difluoro-1,3-dimethyl-2-imidazolidinone, iodine pentafluoride, tris(diethylamino)phosphonium 2,2,3,3,4,4-hexafluorocyclobutanilide, triethylammonium hexafluorocylcobutanilide, hexafluoropropene and the like. Such fluorinating agent can be used alone or in combination of two or more. The fluorinating agent may be appropriately selected or used as solvent, in the range of 1 to 10-fold molar equivalents with respect to the compound represented by Formula (53).


Additives may be used, and examples thereof may include crown ethers such as 18-crown-6, interline transfer catalysts such as a tetraphenylphosphonium salt, inorganic salts such as calcium fluoride and calcium chloride, metal oxides such as mercury oxide, ion exchange resin and the like. Such additives can be not only added to the reaction system but also used as a pretreating agent for the fluorinating agent.


The reaction temperature may be appropriately selected in the range from −80° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately selected in the range from several minutes to 96 hours.


Preparation Process 12




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wherein X1a, X2a, Xaa, X4a, Y1a, Y2a, Y4a, Y5a, G1a, R1a, R2a, Ra, Rb, Rc′ and Rc″ have the same meaning as those described above. A compound represented by Formula (56) can be prepared from the compound represented by Formula (55) according to the process described in Preparation Process 10.


Preparation Process 13




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wherein X1a, X2a, X3a, X4a, Y1a, Y2a, Y4a, Y5a, G1a, G2a, R2a, Ra, Rb, Rc and Q1a have the same meaning as those described above.


A compound represented by Formula (58) can be prepared from the compound represented by Formula (57) according to the process described in Preparation Process 11.


Preparation Process 14




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wherein X1a, X2a, X3a, X4a, Y1a, Y2a, Y4a, Y5a, G1a, G2a, R1a, R2a, Ra, Rb, Rc′, Rc″ and Q1a have the same meaning as those described above.


A compound represented by Formula (60) can be prepared from the compound represented by Formula (59) according to the process described in Preparation Process 10.


In all of the processes for preparation as described in the above, the desired products may be isolated from the reaction system after the reaction is completed according to conventional methods, but if required, purification can be carried out by operations such as recrystallization, column chromatography, distillation and the like. Further, the desired product can be also provided to the subsequent reaction process without being separated from the reaction system.


Hereinbelow, the representative compounds among the compounds represented by Formula (1) as the active ingredient for the insecticide of the invention will be given in Table 1 to Table 5, but the invention is not intended to be limited thereto.


In Table 6 and Table 7, the compound representative of the compound of Formula (6) will be given, but the invention is not intended to be limited thereto.


In Table 8 to Table 10, the compounds representative of the compounds of Formula (8), Formula (11) and Formula (13), but the invention is not intended to be limited thereto.


In addition, the abbreviations in the tables have the following meanings: “n-” represents normal, “Me” a methyl group, “Et” an ethyl group, “n-Pr” a normal propyl group, “i-Pr” an isopropyl group, “n-Bu” a normal butyl group, “i-Bu” an isobutyl group, “s-Bu” a secondary butyl group, “t-Bu” a tertiary butyl group, “H” a hydrogen atom, “O” an oxygen atom, “S” a sulfur atom, “C” a carbon atom, “N” a nitrogen atom, “F” a fluorine atom, “Cl” a chlorine atom, “Br′ a bromine atom, “I” an iodine atom, “CF3” a trifluoromethyl group, “MeS” a methylthio group, “MeSO” methylsulfinyl group, “MeSO2” a methylsulfonyl group, “MeO” a methoxy group, “NH2” an amino group, “MeNH” a methylamino group, and “Me2N” is a dimethylamino group; and “OH” a hydroxyl group, respectively.









TABLE 1









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Comp. No.
Q1
Q2












1
phenyl
2,6-dimethyl-4-(pentafluoroethyl)phenyl


2
phenyl
2,6-dichloro-4-(pentafluoroethyl)phenyl


3
2-fluorophenyl
2,6-dichloro-4-(pentafluoroethyl)phenyl


4
phenyl
2,6-dibromo-4-(pentafluoroethyl)phenyl


5
2-fluorophenyl
2,6-dibromo-4-(pentafluoroethyl)phenyl


6
phenyl
2,6-dichloro-4-(heptafluoroisopropyl)phenyl


7
phenyl
2,6-dibromo-4-(heptafluoroisopropyl)phenyl


8
2-fluorophenyl
2,6-dibromo-4-(heptafluoroisopropyl)phenyl


9
phenyl
2,6-dimethyl-4-(heptafluoro-n-propyl)phenyl


10
phenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


11
2-methylphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


12
3-methylphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


13
4-methylphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


14
2-ethylphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


15
3-ethylphenyl
2,6-dimethyl-4-(heptafluorolsopropyl)phenyl


16
4-ethylphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


17
2-fluorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


18
3-fluorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


19
4-fluorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


20
2-chlorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


21
3-chlorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


22
4-chlorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


23
2-bromophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


24
3-bromophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


25
4-bromophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


26
2-iodophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


27
3-iodophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


28
4-iodophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


29
3-cyanophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


30
4-cyanophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


31
2-nitrophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


32
3-nitrophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


33
4-nitrophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


34
2-aminophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


35
3-aminophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


36
4-aminophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


37
2-trifluoromethylphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


38
3-trifluoromethylphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


39
4-trifluoromethylphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


40
2-hydroxyphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


41
2-methoxyphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


42
3-methoxyphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


43
4-methoxyphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


44
2-phenoxyphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


45
4-(1,1-dimethylethyl)phenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


46
3-(dimethylamino)phenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


47
4-(dimethylamino)phenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


48
4-trifluoromethoxyphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


49
2-(acetylamino)phenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


50
3-(acetylamino)phenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


51
4-(acetylamino)phenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


52
2-acetoxyphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


53
2-(methoxycarbonyl)phenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


54
4-(methoxycarbonyl)phenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


55
2-(4-trifluoromethylphenyl)
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl



phenyl



56
2,3-dimethylphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


57
2,4-dimethylphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


58
2,6-dimethylphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


59
2,3-difluorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


60
2,4-difluorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


61
2,5-difluorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


62
2,6-difluorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


63
3,4-difluorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


64
3,5-difluorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


65
2,3-dichlorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


66
2,4-dichlorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


67
2,5-dichlorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


68
2,6-dichlorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


69
3,4-dichlorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


70
2,4-dinitrophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


71
3,4-dinitrophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


72
2,6-dimethoxyphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


73
3,5-dimethoxyphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


74
3-methyl-4-nitrophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


75
5-amino-2-fluorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


76
3-fluoro-2-methylphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


77
2-fluoro-5-nitrophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


78
4-fluoro-3-nitrophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


79
5-fluoro-2-nitrophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


80
2-fluoro-6-iodophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


81
2-fluoro-5-trifluoromethylphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


82
2-chloro-4-nitrophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


83
2-chloro-4-fluorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


84
2-chloro-6-fluorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


85
3-chloro-4-fluorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


86
4-chloro-2-fluorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


87
4-chloro-2-nitrophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


88
3-methoxy-4-nitrophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


89
2-methoxy-4-nitrophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


90
2,3,4-trifluorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


91
2,4,6-trimethylphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


92
2,3,6-trifluorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


93
2,4,5-trimethoxyphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


94
3,4,5-trimethoxyphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


95
2,3,4,5,6-pentafluorophenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


96
2-biphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


97
3-biphenyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


98
1-naphthyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


99
2-naphthyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


100
pyridin-2-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


101
pyridin-3-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


102
pyridin-4-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


103
2-methylpyridin-5-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


104
3-methylpyridin-2-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


105
2-fluoropyridin-3-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


106
2-chloropyridin-3-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


107
2-chloropyridin-4-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


108
2-chloropyridin-6-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


109
2-chloropyridin-5-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


110
5-chloropyridin-2-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


111
4-trifluoromethylpyridin-3-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


112
3-hydroxypyridin-2-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


113
2-phenoxypyridin-3-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


114
2-methylthiopyridin-3-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


115
2,6-dimethoxypyridin-3-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


116
2,3-dichloropyridin-5-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


117
2,5-dichloropyridin-3-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


118
2,6-dichloropyridin-3-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


119
3,5-dichloropyridin-4-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


120
(pyridine-N-oxide)-2-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


121
N-methylpyrrol-2-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


122
pyrazin-2-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


123
2-methylpyrazin-5-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


124
4-trifluoromethylpyrimidin-5-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


125
furan-2-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


126
furan-3-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


127
2-tetrahydrofuranyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


128
3-tetrahydrofuranyl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


129
benzofuran-2-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


130
tetrahydropyran-2-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


131
2-methyl-5,6-dihydro-4Hpyran-3-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


132
thiophen-2-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


133
thiophen-3-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


134
3-methylthiophen-2-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


135
2-nitrothiophen-4-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


136
2-methylthiophen-5-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


137
3-chlorothiophen-2-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


138
2-chlorothiophen-5-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


139
3-bromothiophen-2-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


140
2-bromothiophen-5-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


141
3-iodothiophen-2-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


142
3-phenylthiophen-2-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


143
2,4-dimethylthiophen-5-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


144
benzothiophen-2-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


145
4-nitro-1H-pyrrol-2-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


146
3-ethyl-3H-pyrazol-4-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


147
1-methyl-3-nitro-1H-pyrazol-4-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


148
3-chloro-1-methyl-1H-pyrazol-4-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


149
3-bromo-1-methyl-1H-pyrazo1-4-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


150
1-methyl-3-trifluoromethyl-
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl



1H-pyrazol-4-yl



151
1-methyl-5-trifluoromethyl-
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl



1H-pyrazol-4-yl



152
isoxazol-5-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


153
4-trifluoromethylthiazol-5-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


154
2,4-dimethylthiazol-5-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


155
2-ethyl-4-methylthiazol-5-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


156
2-chloro-4-methylthiazol-5-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


157
3-methyl-isothiazol-5-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


158
3,4-dichloro-isothiazol-5-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


159
3-chlorobenzothiazol-2-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


160
2,2-difluoro-benzo[1.3]dioxol-5-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


161
2,2-difluoro-benzo[1.3]dioxol-4-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


162
2-phenylquinolin-4-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


163
phenyl
2-bromo-4-(heptafluoroisopropyl)-6-methylphenyl


164
phenyl
2-ethyl-4-(heptafluoroisopropyl)-6-methylphenyl


165
2-fluorophenyl
2-ethyl-4-(heptafluoroisopropyl)-6-methylphenyl


166
phenyl
4-(heptafluoroisopropyl)-2-iodo-6-methylphenyl


167
phenyl
4-(heptafluoroisopropyl)-2-hydroxy-




6-methylphenyl


168
phenyl
2-chloro-6-ethyl-4-(heptafluoroisopropyl)phenyl


169
phenyl
2-bromo-6-ethyl-4-(heptafluoroisopropyl)phenyl


170
2-fluorophenyl
2-bromo-6-ethyl-4-(heptafluoroisopropyl)phenyl


171
phenyl
2-ethyl-4-(heptafluoroisopropyl)-




6-iodophenyl


172
2-fluorophenyl
2-ethyl-4-(heptafluoroisopropyl)-




6-iodophenyl


173
4-nitrophenyl
2-ethyl-4-(heptafluoroisopropyl)-




6-iodophenyl


174
4-cyanophenyl
2-ethyl-4-(heptafluoroisopropyl)-




6-iodophenyl


175
4-nitrophenyl
4-(heptafluoroisopropyl)-2-methyl-




6-n-propylphenyl


176
phenyl
4-(heptafluoroisopropyl)-




2-isopropyl-6-methylphenyl


177
2-fluorophenyl
4-(heptafluoroisopropyl)-




2-isopropyl-6-methylphenyl


178
phenyl
2-bromo-4-(heptafluoroisopropyl)-




6-n-propylphenyl


179
2-fluorophenyl
2-bromo-4-(heptafluoroisopropyl)-




6-n-propylphenyl


180
4-nitrophenyl
2-bromo-4-(heptafluoroisopropyl)-




6-n-propylphenyl


181
4-cyanophenyl
2-bromo-4-(heptafluoroisopropyl)-




6-n-propylphenyl


182
phenyl
4-(heptafluoroisopropyl)-2-iodo-




6-n-propylphenyl


183
2-fluorophenyl
4-(heptafluoroisopropyl)-2-iodo-




6-n-propylphenyl


184
4-nitrophenyl
4-(heptafluoroisopropyl)-2-iodo-




6-n-propylphenyl


185
4-cyanophenyl
4-(heptafluoroisopropyl)-2-iodo-




6-n-propylphenyl


186
4-trifluoromethylphenyl
4-(heptafluoroisopropyl)-2-iodo-




6-n-propylphenyl


187
phenyl
2-chloro-4-(heptafluoroisopropyl)-




6-n-butylphenyl


188
2-fluorophenyl
2-chloro-4-(heptafluoroisopropyl)-




6-n-butylphenyl


189
phenyl
2-bromo-4-(heptafluoroisopropyl)-




6-n-butylphenyl


190
2-fluorophenyl
2-bromo-4-(heptafluoroisopropyl)-




6-n-butylphenyl


191
phenyl
4-(heptafluoroisopropyl)-2-iodo-6-n-butylphenyl


192
2-fluorophenyl
4-(heptafluoroisopropyl)-2-iodo-6-n-butylphenyl


193
phenyl
2-(2-butyl)-6-chloro-4-(heptafluoroisopropyl)phenyl


194
phenyl
2-bromo-6-(2-butyl)-4-(heptafluoroisopropyl)phenyl


195
2-fluorophenyl
2-bromo-6-(2-butyl)-4-(heptafluoroisopropyl)phenyl


196
phenyl
2-(2-butyl)-4-(heptafluoroisopropyl)-6-iodophenyl


197
2-fluorophenyl
2-bromo-6-cyano-4-(heptafluoroisopropyl)phenyl


198
phenyl
2-bromo-4-(heptafluoroisopropyl)-6-methylthiophenyl


199
2-fluorophenyl
2-bromo-4-(heptafluoroisopropyl)-6-methylthiophenyl


200
phenyl
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfinyl)phenyl


201
2-fluorophenyl
2-chloro-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


202
2-chloropyridin-3-yl
2-chloro-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


203
phenyl
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


204
2-fluorophenyl
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


205
4-fluorophenyl
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


206
4-nitrophenyl
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


207
4-cyanophenyl
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


208
2-chloropyridin-3-yl
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


209
phenyl
4-(heptafluoroisopropyl)-2-methylthiomethyl-6-trifluoromethylphenyl


210
phenyl
2-bromo-4-(heptafluoroisopropyl)-6-(trifluoromethylthio)phenyl


211
phenyl
2,6-dimethyl-4-(nonafluoro-n-butyl)phenyl


212
phenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


213
2-methylphenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


214
4-methylphenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


215
2-fluorophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


216
3-fluorophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


217
4-fluorophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


218
2-chlorophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


219
4-chlorophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


220
2-bromophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


221
2-iodophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


222
3-cyanophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


223
4-cyanophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


224
2-nitrophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


225
3-nitrophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


226
4-nitrophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


227
2-trifluoromethylphenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


228
4-trifluoromethylphenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


229
4-trifluoromethoxyphenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


230
2,3-difluorophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


231
2,4-difluorophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


232
2,5-difluorophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


233
2,6-difluorophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


234
2,4-dichlorophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


235
2,6-dichlorophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


236
3,4-dichlorophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


237
2-chloro-4-nitrophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


238
2-chloro-4-fluorophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


239
2-chloro-6-fluorophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


240
4-chloro-2-fluorophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


241
4-chloro-2-nitrophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


242
2,3,6-trifluorophenyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


243
pyridin-2-yl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


244
pyridin-3-yl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


245
2-fluoropyridin-3-yl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


246
2-chloropyridin-3-yl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


247
2-chloropyridin-5-yl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


248
2-methylthiopyridin-3-yl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


249
pyrazin-2-yl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


250
furan-2-yl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


251
furan-3-yl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


252
2-tetrahydrofuranyl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


253
benzofuran-2-yl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


254
thiophen-2-yl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


255
2,6-difluorophenyl
2,6-dichloro-4-(trifluoromethylthio)phenyl


256
phenyl
2,6-dibromo-4-(trifluoromethylthio)phenyl


257
2,6-difluorophenyl
2,6-dibromo-4-(trifluoromethylthio)phenyl


258
phenyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl


259
2-fluorophenyl
2,6-dibromo-4-(pentafluoroethylthio)phenyl


260
phenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


261
2-fluorophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


262
phenyl
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl


263
phenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


264
2-methylphenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


265
4-methylphenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


266
2-fluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


267
3-fluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


268
4-fluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


269
2-chlorophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


270
4-chlorophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


271
2-bromophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


272
2-iodophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


273
3-cyanophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


274
4-cyanophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


275
2-nitrophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


276
3-nitrophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


277
4-nitrophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


278
2-trifluoromethylphenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


279
4-trifluoromethylphenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


280
4-trifluoromethoxyphenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


281
2,3-difluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


282
2,4-difluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


283
2,5-difluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


284
2,6-difluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


285
3-aminophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


286
3-(acetylamino)phenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


287
3-(methylsulfonylamino)phenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


288
2,4-dinitrophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


289
3,4-dinitrophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


290
3-methyl-4-nitrophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


291
5-amino-2-fluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


292
2-fluoro-5-nitrophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


293
2-fluoro-
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



5-(methylsulfonylamino)phenyl



294
2-methoxy-4-nitrophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


295
3-methoxy-4-nitrophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


296
5-(acetylamino)-2-fluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


297
2,4-dichlorophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


298
2,6-dichlorophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


299
3,4-dichlorophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


300
2-chloro-4-nitrophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


301
2-chloro-4-fluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


302
2-chloro-6-fluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


303
4-chloro-2-fluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


304
4-chloro-2-nitrophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


305
2,3,6-trifluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


306
pyridin-2-yl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


307
pyridin-3-yl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


308
2-fluoropyridin-3-yl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


309
2-chloropyridin-3-yl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


310
2-chloropyridin-5-yl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


311
2-methylthiopyridin-3-yl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


312
2,6-dichloropyridin-3-yl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


313
2,6-dichloropyridin-4-yl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


314
2-chloro-6-methylpyridin-3-yl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


315
pyridin-N-oxide-2-yl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


316
pyrazin-2-yl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


317
1-methyl-3-nitro-
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



1Hpyrazol-4-yl



318
1-methyl-3-trifluoromethyl-
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



1Hpyrazo1-4-yl



319
1-methyl-5-trifluoromethyl-
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



1Hpyrazol-4-yl



320
2-tetrahydrofuranyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


321
2-phenylthiazol-4-yl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


322
furan-2-yl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


323
furan-3-yl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


324
2-tetrahydrofuranyl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


325
benzofuran-2-yl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


326
thiophen-2-yl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


327
phenyl
2,6-diiodo-4-(heptafluoro-n-propylthio)phenyl


328
2-fluorophenyl
2,6-diiodo-4-(heptafluoro-n-propylthio)phenyl


329
phenyl
2,6-dichloro-4-(heptafluoroisopropylthio)phenyl


330
2-fluorophenyl
2,6-dichloro-4-(heptafluoroisopropylthio)phenyl


331
2-chloropyridin-3-yl
2,6-dichloro-4-(heptafluoroisopropylthio)phenyl


332
phenyl
2,6-dibromo-4-(heptafluoroisopropylthio)phenyl


333
phenyl
2,6-dibromo-4-(nonafluoro-n-butylthio)phenyl


334
2-fluorophenyl
2,6-dibromo-4-(nonafluoro-n-butylthio)phenyl


335
phenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


336
2-methylphenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


337
4-methylphenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


338
2-fluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


339
3-fluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


340
4-fluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


341
2-chlorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


342
4-chlorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


343
2-bromophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


344
2-iodophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


345
3-cyanophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


346
4-cyanophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


347
2-nitrophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


348
3-nitrophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


349
4-nitrophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


350
2-trifluoromethylphenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


351
4-trifluoromethylphenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


352
4-trifluoromethoxyphenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


353
2,3-difluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


354
2,4-difluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


355
2,5-difluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


356
2,6-difluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


357
2,4-dichlorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


358
2,6-dichlorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


359
3,4-dichlorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


360
2-chloro-4-nitrophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


361
2-chloro-4-fluorophenyl
2,6-dibromo-4-(heptatluoro-n-propylsulfinyl)phenyl


362
2-chloro-6-fluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


363
4-chloro-2-fluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


364
4-chloro-2-nitrophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


365
2,3,6-trifluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


366
pyridin-2-yl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


367
pyridin-3-yl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


368
2-fluoropyridin-3-yl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


369
2-chloropyridin-3-yl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


370
2-chloropyridin-5-yl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


371
2-methylthiopyridin-3-yl
2,6-dibromo-4-(heptafluoro-n-propylsulflnyl)phenyl


372
pyrazin-2-yl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


373
furan-2-yl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


374
thiophen-2-yl
2,6-dibromo-4-(heptafluoro-n-propylsulflnyl)phenyl


375
2,6-difluorophenyl
2,6-dichloro-4-(trifluoromethylsulfonyl)phenyl


376
phenyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl


377
2,6-difluorophenyl
2,6-dibromo-4-(trifluoromethylsulfonyl)phenyl


378
2-fluorophenyl
2,6-dichloro-4-(heptafluoroisopropylsulfonyl)phenyl


379
phenyl
2,6-dichloro-4-(heptafluoroisopropylsulfonyl)phenyl


380
phenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


381
2-methylphenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


382
4-methylphenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


383
2-fluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


384
3-fluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


385
4-fluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


386
2-chlorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


387
4-chlorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


388
2-bromophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


389
2-iodophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


390
3-cyanophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


391
4-cyanophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


392
2-nitrophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


393
3-nitrophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


394
4-nitrophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


395
2-trifluoromethylphenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


396
4-trifluoromethylphenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


397
4-trifluoromethoxyphenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


398
2,3-difluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


399
2,4-difluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


400
2,5-difluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


401
2,6-difluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


402
2,4-dichlorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


403
2,6-dichlorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


404
3,4-dichlorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


405
2-chloro-4-nitrophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


406
2-chloro-4-fluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


407
2-chloro-6-fluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


408
4-chloro-2-fluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


409
4-chloro-2-nitrophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


410
2,3,6-trifluorophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


411
pyridin-2-yl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


412
pyridin-3-yl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


413
2-fluoropyridin-3-yl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


414
2-chloropyridin-3-yl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


415
2-chloropyridin-5-yl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


416
2-methylthiopyridin-3-yl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


417
pyrazin-2-yl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


418
furan-2-yl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


419
thiophen-2-yl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


420
phenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


421
2-methylphenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


422
4-methylphenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


423
2-fluorophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


424
3-fluorophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


425
4-fluorophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


426
2-chlorophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


427
4-chlorophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


428
2-bromophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


429
2-iodophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


430
3-cyanophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


431
4-cyanophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


432
2-nitrophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


433
3-nitrophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


434
4-nitrophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


435
2-trifluoromethylphenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


436
4-trifluoromethylphenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


437
4-trifluoromethoxyphenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


438
2,3-difluorophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


439
2,4-difluorophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


440
2,5-difluorophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


441
2,6-difluorophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


442
2,4-dichlorophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


443
2,6-dichlorophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


444
3,4-dichlorophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


445
2-chloro-4-nitrophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


446
2-chloro-4-fluorophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


447
2-chloro-6-fluorophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


448
4-chloro-2-fluorophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


449
4-chloro-2-nitrophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


450
2,3,6-trifluorophenyl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


451
pyridin-2-yl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


452
pyridin-3-yl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


453
2-fluoropyridin-3-yl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


454
2-chloropyridin-3-yl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


455
2-chloropyridin-5-yl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


456
2-methylthiopyridin-3-yl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


457
pyrazin-2-yl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


458
furan-2-yl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


459
thiophen-2-yl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


460
2,6-difluorophenyl
2,6-dichloro-4-(trifluoromethylsulfonyl)phenyl


461
phenyl
2-bromo-6-(heptafluoroisopropyloxy)-4-methylpyridin-3-yl


462
2-fluorophenyl
2-bromo-6-(heptafluoroisopropyloxy)-4-methylpyridin-3-yl


463
phenyl
2,4-dimethyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy)




pyridin-3-yl


464
phenyl
2-chloro-4-methyl-6-(2,2,2-trifIuoro-1-trifluoromethylethoxy)




pyridin-3-yl


465
phenyl
2-bromo-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy)




pyridin-3-yl


466
2-fluorophenyl
2-bromo-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy)




pyridin-3-yl


467
phenyl
2-iodo-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy)




pyridin-3-yl
















TABLE 2









embedded image


















Comp. No.
Q1
X1
X2
X3
X4
Q2





601
phenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


602
2-methylphenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


603
3-methylphenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


604
4-methylphenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


605
2-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


606
3-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


607
4-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


608
3-cyanophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


609
4-cyanophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


610
2-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


611
3-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


612
4-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


613
2-chlorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


614
4-chlorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


615
2-bromophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


616
2-iodophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


617
2-trifluoromethylphenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


618
4-trifluoromethylphenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


619
4-trifluoromethoxyphenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


620
4-(dimethylamino)phenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


621
2.3-difluorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


622
2.4-difluorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


623
2.5-difluorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


624
2,6-difluorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


625
2,4-dichlorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


626
2,6-dichlorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


627
3,4-dichlorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


628
2-fluoro-4-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


629
4-fluoro-2-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


630
2-chloro-4-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


631
4-chloro-2-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


632
2-chloro-6-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


633
2-chloro-4-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


634
4-chloro-2-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


635
2,3,6-trifluorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


636
pyridin-2-yl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


637
pyridin-3-yl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


638
2-fluoropyridin-3-yl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


639
2-chloropyridin-3-yl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


640
2-chloropyridin-5-yl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


641
2-methylthiopyridin-3-yl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


642
pyrazin-2-yl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


643
furan-2-yl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


644
furan-3-yl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


645
2-tetrahydrofuranyl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


646
benzofuran-2-yl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


647
thiophen-2-yl
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


648
2-methyl-5,6-dihydro-
F
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl



4H-pyran-3-yl







649
phenyl
H
Cl
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


650
phenyl
H
F
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


651
4-nitrophenyl
H
F
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


652
4-cyanophenyl
H
F
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


653
4-fluorophenyl
H
F
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


654
4-fluorophenyl
H
F
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


655
4-trifluoromethylphenyl
H
F
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


656
2.4-difluorophenyl
H
F
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


657
2-chloropyridin-3-yl
H
F
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


658
phenyl
H
H
CF3
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


659
phenyl
H
H
H
F
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


660
phenyl
H
H
H
Cl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


661
phenyl
H
H
H
Br
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


662
phenyl
H
H
H
I
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


663
phenyl
F
H
H
F
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


664
phenyl
H
Br
H
Br
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


665
phenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


666
2-methylphenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


667
4-methylphenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


668
2-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


669
3-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


670
4-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


671
2-chlorophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


672
4-chlorophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


673
2-bromophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


674
2-iodophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


675
3-cyanophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


676
4-cyanophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


677
2-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


678
3-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


679
4-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


680
2-trifluoromethylphenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


681
4-trifluoromethylphenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


682
4-trifluoromethoxyphenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


683
2.3-difluorophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


684
2.4-difluorophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


685
2.5-difluorophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


686
2,6-difluorophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


687
2,4-dichlorophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


688
2,6-dichlorophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


689
3,4-dichlorophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


690
2-chloro-4-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


691
2-chloro-4-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


692
2-chloro-6-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


693
4-chloro-2-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


694
4-chloro-2-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


695
2,3,6-trifluorophenyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


696
pyridin-2-yl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


697
pyridin-3-yl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


698
2-fluoropyridin-3-yl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


699
2-chloropyridin-3-yl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


700
2-chloropyridin-5-yl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


701
2-methylthiopyridin-3-yl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


702
pyrazin-2-yl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


703
furan-2-yl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


704
furan-3-yl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


705
2-tetrahydrofuranyl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


706
benzofuran-2-yl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


707
thiophen-2-yl
F
H
H
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


708
phenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


709
2-methylphenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


710
4-methylphenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


711
2-fluorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


712
3-fluorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


713
4-fluorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


714
2-chlorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


715
4-chlorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


716
2-bromophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


717
2-iodophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


718
3-cyanophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


719
4-cyanophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


720
2-nitrophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


721
3-nitrophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


722
4-nitrophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


723
2-trifluoromethylphenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


724
4-trifluoromethylphenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


725
4-trifluoromethoxyphenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


726
2,3-difluorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


727
2,4-difluorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


728
2,5-difluorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


729
2,6-difluorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


730
2,4-dichlorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


731
2,6-dichlorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


732
3,4-dichlorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


733
2-chloro-4-nitrophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


734
2-chloro-4-fluorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


735
2-chloro-6-fluorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


736
4-chloro-2-fluorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


737
4-chloro-2-nitrophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


738
2,3,6-trifluorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


739
pyridin-2-yl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


740
pyridin-3-yl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


741
2-fluoropyridin-3-yl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


742
2-chloropyridin-3-yl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


743
2-chloropyridin-5-yl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


744
2-methylthiopyridin-3-yl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


745
pyrazin-2-yl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


746
furan-2-yl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


747
furan-3-yl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


748
2-tetrahydrofuranyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


749
benzofuran-2-yl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


750
thiophen-2-yl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


751
phenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


752
2-methylphenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


753
4-methylphenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


754
2-fluorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


755
3-fluorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


756
4-fluorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


757
2-chlorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


758
4-chlorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


759
2-bromophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


760
2-iodophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


761
3-cyanophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


762
4-cyanophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


763
2-nitrophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


764
3-nitrophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


765
4-nitrophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


766
2-trifluoromethylphenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


767
4-trifluoromethylphenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


768
4-trifluoromethoxyphenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


769
2,3-difluorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


770
2,4-difluorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


771
2,5-difluorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


772
2,6-difluorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


773
2,4-dichlorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


774
2,6-dichlorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


775
3,4-dichlorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


776
2-chloro-4-nitrophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


777
2-chloro-4-fluorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


778
2-chloro-6-fluorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


779
4-chloro-2-fluorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


780
4-chloro-2-nitrophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


781
2,3,6-trifluorophenyl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


782
pyridin-2-yl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


783
pyridin-3-yl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


784
2-fluoropyridin-3-yl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


785
2-chloropyridin-3-yl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


786
2-chloropyridin-5-yl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


787
2-methylthiopyridin-3-yl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


788
pyrazin-2-yl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


789
furan-2-yl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


790
thiophen-2-yl
F
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


791
phenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


792
2-methylphenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


793
4-methylphenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


794
2-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


795
3-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


796
4-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


797
2-chlorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


798
4-chlorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


799
2-bromophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


800
2-iodophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


801
3-cyanophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


802
4-cyanophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


803
2-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


804
3-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


805
4-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


806
2-trifluoromethylphenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


807
4-trifluoromethylphenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


808
4-trifluoromethoxyphenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


809
2,3-difluorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


810
2,4-difluorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


811
2,5-difluorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


812
2,6-difluorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


813
2,4-dichlorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


814
2,6-dichlorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


815
3,4-dichlorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


816
2-chloro-4-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


817
2-chloro-4-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


818
2-chloro-6-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


819
4-chloro-2-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


820
4-chloro-2-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


821
2,3,6-trifluorophenyl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


822
pyridin-2-yl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


823
pyridin-3-yl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


824
2-fluoropyridin-3-yl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


825
2-chloropyridin-3-yl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


826
2-chloropyridin-5-yl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


827
2-methylthiopyridin-3-yl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


828
pyrazin-2-yl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


829
furan-2-yl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


830
thiophen-2-yl
F
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


831
phenyl
Cl
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


832
2-fluorophenyl
Cl
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


833
2-chloropyridin-3-yl
Cl
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
















TABLE 3









embedded image


















Comp.








No.
Q1
R1
R2
X1
X2
Q2





1001
phenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1002
2-methylphenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1003
4-methylphenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1004
2-fluorophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1005
3-fluorophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1006
4-fluorophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1007
2-chlorophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1008
4-chlorophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1009
2-bromophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1010
2-iodophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1011
3-cyanophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1012
4-cyanophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1013
2-nitrophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1014
3-nitrophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1015
4-nitrophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1016
2-trifluoromethylphenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1017
4-trifluoromethylphenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1018
4-trifluoromethoxyphenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1019
2,3-difluorophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1020
2,4-difluorophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1021
2,5-difluorophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1022
2,6-difluorophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1023
2,4-dichlorophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1024
2,6-dichlorophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1025
3,4-dichlorophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1026
2-chloro-4-nitrophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1027
2-chloro-4-fluorophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1028
2-chloro-6-fluorophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1029
4-chloro-2-fluorophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1030
4-chloro-2-nitrophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1031
2,3,6-trifluorophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1032
3-(acetylamino)phenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1033
pyridin-2-yl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1034
pyridin-3-yl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1035
2-fluoropyridin-3-yl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1036
2-chloropyridin-3-yl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1037
2-chloropyridin-5-yl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1038
2-trifluoromethylpyridin-
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl



3-yl







1039
2-methylthiopyridin-3-yl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1040
pyrazin-2-yl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1041
furan-2-yl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1042
furan-3-yl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1043
2-tetrahydrofuranyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1044
benzofuran-2-yl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1045
thiophen-2-yl
Me
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1046
phenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1047
2-methylphenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1048
4-methylphenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1049
2-fluorophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6








-(methylsulfonyl)phenyl


1050
3-fluorophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1051
4-fluorophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1052
2-chlorophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1053
4-chlorophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1054
2-bromophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1055
2-iodophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1056
3-cyanophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1057
4-cyanophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1058
2-nitrophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1059
3-nitrophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1060
4-nitrophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1061
2-trifluoromethylphenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1062
4-trifluoromethylphenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1063
4-trifluoromethoxyphenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1064
2,3-difluorophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1065
2,4-difluorophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1066
2,5-difluorophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1067
2,6-difluorophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1068
2,4-dichlorophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1069
2,6-dichlorophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1070
3,4-dichlorophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1071
2-chloro-4-nitrophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1072
2-chloro-4-fluorophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1073
2-chloro-6-fluorophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1074
4-chloro-2-fluorophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1075
4-chloro-2-nitrophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1076
2,3,6-trifluorophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1077
pyridin-2-yl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1078
pyridin-3-yl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1079
2-fluoropyridin-3-yl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1080
2-chloropyridin-3-yl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1081
2-chloropyridin-5-yl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1082
2-methylthiopyridin-
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-



3-yl




(methylsulfonyl)phenyl


1083
pyrazin-3-yl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1084
furan-2-yl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1085
thiophen-2-yl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-








(methylsulfonyl)phenyl


1086
phenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1087
2-methylphenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1088
4-methylphenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1089
2-fluorophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1090
3-fluorophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1091
4-fluorophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1092
2-chlorophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1093
4-chlorophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1094
2-bromophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1095
2-iodophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1096
3-cyanophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1097
4-cyanophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1098
2-nitrophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1099
3-nitrophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1100
4-nitrophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1101
2-trifluoromethylphenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1102
4-trifluoromethylphenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1103
4-trifluoromethoxyphenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1104
2,3-difluorophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1105
2,4-difluorophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1106
2,5-difluorophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1107
2,6-difluorophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1108
2,4-dichlorophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1109
2,6-dichlorophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1110
3,4-dichlorophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1111
2-chloro-4-nitrophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1112
2-chloro-4-fluorophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1113
2-chloro-6-fluorophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1114
4-chloro-2-fluorophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1115
4-chloro-2-nitrophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1116
2,3,6-trifluorophenyl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1117
pyridin-2-yl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1118
pyridin-3-yl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1119
2-fluoropyridin-3-yl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1120
2-chloropyridin-3-yl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1121
2-chloropyridin-5-yl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1122
2-methylthiopyridin-
Me
H
H
H
2-n-propyl-6-iodo-4-



3-yl




(heptafluoroisopropyl)phenyl


1123
pyrazin-2-yl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1124
furan-2-yl
Me
H
H
H
2-n-propyl-6-iodo-4-








(heptafluoroisopropyl)phenyl


1125
2-fluorophenyl
Me
H
H
H
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl


1126
phenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1127
2-methylpenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1128
4-methylphenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1129
2-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1130
3-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1131
4-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1132
2-chlorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1133
4-chlorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1134
2-bromophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1135
2-iodophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1136
3-cyanophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1137
4-cyanophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1138
2-nitrophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1139
3-nitrophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1140
4-nitrophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1141
2-trifluoromethylphenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1142
4-trifluoromethylphenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1143
4-trifluoromethoxyphenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1144
2,3-difluorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1145
2,4-difluorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1146
2,5-difluorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1147
2,6-difluorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1148
2,4-dichlorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1149
2,6-dichlorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1150
3,4-dichlorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1151
2-chloro-4-nitrophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1152
2-chloro-4-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1153
2-chloro-6-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1154
4-chloro-2-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1155
4-chloro-2-nitrophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1156
2,3,6-trifluorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1157
pyridin-2-yl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1158
pyridin-3-yl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1159
2-fluoropyridin-3-yl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1160
2-chloropyridin-3-yl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1161
2-chloropyridin-5-yl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1162
2-methylthiopyridin-3-yl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1163
pyrazin-2-yl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1164
furan-2-yl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1165
thiophen-2-yl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1166
phenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1167
2-methylphenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1168
4-methylphenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1169
2-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1170
3-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1171
4-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1172
2-chlorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1173
4-chlorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1174
2-bromophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1175
2-iodophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1176
3-cyanophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1177
4-cyanophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1178
2-nitrophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1179
3-nitrophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1180
4-nitrophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1181
2-trifluoromethylphenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1182
4-trifluoromethylphenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1183
4-trifluoromethoxyphenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1184
2,3-difluorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1185
2,4-difluorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1186
2,5-difluorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1187
2,6-difluorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1188
2,4-dichlorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1189
2,6-dichlorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1190
3,4-dichlorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1191
2-chloro-4-nitrophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1192
2-chloro-4-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1193
2-chloro-6-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1194
4-chloro-2-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1195
4-chloro-2-nitrophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1196
2,3,6-trifluorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1197
pyridin-2-yl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1198
pyridin-3-yl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1199
2-fluoropyridin-3-yl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1200
2-chloropyridin-3-yl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1201
2-chloropyridin-5-yl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1202
2-methylthiopyridin-3-yl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1203
pyrazin-2-yl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1204
furan-2-yl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1205
thiophen-2-yl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1206
2-fluorophenyl
Et
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1207
pyridin-3-yl
Et
H
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1208
phenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1209
2-methylphenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1210
3-methylphenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1211
4-methylphenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1212
2-nitrophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1213
3-nitrophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1214
4-nitrophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1215
2-cyanophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1216
3-cyanophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1217
4-cyanophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1218
2-fluorophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1219
3-fluorophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1220
4-fluorophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1221
2-chlorophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1222
4-chlorophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1223
2-bromophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1224
2-iodopehnyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1225
2-trifluoromethylphenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1226
4-trifluoromethylphenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1227
4-trifluoromethoxyphenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1228
2,3-difluorophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1229
2.4-difluorophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1230
2,5-difluorophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1231
2,6-difluorophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1232
2,4-dichlorophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1233
2,6-dichlorophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1234
3,4-dichlorophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1235
2-fluoro-4-nitrophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1236
4-fluoro-2-nitrophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1237
2-chloro-4-fluorophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1238
4-chloro-2-fluorophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1239
2-chloro-6-fluorophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1240
2-chloro-4-nitrophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1241
4-chloro-2-nitrophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1242
2,3,6-trifluorophenyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1243
pyridin-2-yl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1244
pyridin-3-yl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1245
2-chloropyridin-3-yl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1246
2-fluoropyridin-3-yl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1247
2-chloropyridin-5-yl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1248
2-methylthiopyridin-3-yl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1249
pyrazin-2-yl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1250
furan-2-yl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1251
furan-3-yl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1252
2-tetrahydrofuranyl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1253
benzofuran-2-yl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1254
thiophen-2-yl
Me
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1255
phenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1256
2-methylphenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1257
3-methylphenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1258
4-methylphenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1259
2-nitrophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1260
3-nitrophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1261
4-nitrophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1262
2-cyanophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1263
3-cyanophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1264
4-cyanophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1265
2-fluorophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1266
3-fluorophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1267
4-fluorophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1268
2-chlorophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1269
4-chlorophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1270
2-bromophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1271
2-iodophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1272
2-trifluoromethylphenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1273
4-trifluoromethylphenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1274
4-trifluoromethoxyphenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1275
2,3-difluorophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1276
2.4-difluorophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1277
2,5-difluorophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1278
2,6-difluorophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1279
2,4-dichlorophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1280
2,6-dichlorophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1281
3,4-dichlorophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1282
2-fluoro-4-nitrophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1283
4-fluoro-2-nitrophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1284
2-chloro-4-fluorophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1285
4-chloro-2-fluorophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1286
2-chloro-6-fluorophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1287
2-chloro-4-nitrophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1288
4-chloro-2-nitrophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1289
2,3,6-trifluorophenyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1290
pyridin-2-yl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1291
pyridin-3-yl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1292
2-fluoropyridin-3-yl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1293
2-chloropyridin-3-yl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1294
2-chloropyridin-5-yl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1295
2-methylthiopyridin-3-yl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1296
pyrazin-2-yl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1297
furan-2-yl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1298
furan-3-yl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1299
2-tetrahydrofuranyl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1300
benzofuran-2-yl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1301
thiophen-2-yl
Me
H
F
H
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


1302
phenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1303
2-methylphenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1304
4-methylphenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1305
2-fluorophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1306
3-fluorophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1307
4-fluorophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1308
2-chlorophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1309
4-chlorophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1310
2-bromophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1311
2-iodophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1312
3-cyanophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1313
4-cyanophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1314
2-nitrophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1315
3-nitrophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1316
4-nitrophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1317
2-trifluoromethylphenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1318
4-trifluoromethylphenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1319
4-trifluoromethoxyphenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1320
2,3-difluorophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1321
2,4-difluorophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1322
2,5-difluorophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1323
2,6-difluorophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1324
2,4-dichlorophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1325
2,6-dichlorophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1326
3,4-dichlorophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1327
2-chloro-4-nitrophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1328
2-chloro-4-fluorophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1329
2-chloro-6-fluorophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1330
4-chloro-2-fluorophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1331
4-chloro-2-nitrophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1332
2,3,6-trifluorophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1333
pyridin-2-yl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1334
pyridin-3-yl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1335
2-fluoropyridin-3-yl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1336
2-chloropyridin-3-yl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1337
2-chloropyridin-5-yl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1338
2-methylthiopyridin-3-yl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1339
pyrazin-2-yl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1340
furan-2-yl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1341
thiophen-2-yl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1342
phenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1343
2-methylphenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1344
4-methylphenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1345
2-fluorophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1346
3-fluorophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1347
4-fluorophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1348
2-chlorophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1349
4-chlorophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1350
2-bromophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1351
2-iodophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1352
3-cyanophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1353
4-cyanophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1354
2-nitrophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1355
3-nitrophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1356
4-nitrophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1357
2-trifluoromethylphenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1358
4-trifluoromethylphenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1359
4-trifluoromethoxyphenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1360
2,3-difluorophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1361
2,4-difluorophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1362
2,5-difluorophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1363
2,6-difluorophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1364
2,4-dichlorophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1365
2,6-dichlorophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1366
3,4-dichlorophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1367
2-chloro-4-nitrophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1368
2-chloro-4-fluorophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1369
2-chloro-6-fluorophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1370
4-chloro-2-fluorophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1371
4-chloro-2-nitrophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1372
2,3,6-trifluorophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1373
pyridin-2-yl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1374
pyridin-3-yl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1375
2-fluoropyridin-3-yl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1376
2-chloropyridin-3-yl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1377
2-chloropyridin-5-yl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1378
2-methylthiopyridin-3-yl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1379
pyrazin-2-yl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1380
furan-2-yl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1381
thiophen-2-yl
Me
H
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1382
phenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1383
2-methylphenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1384
4-methylphenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1385
2-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1386
3-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1387
4-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1388
2-chlorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1389
4-chlorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1390
2-bromophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1391
2-iodophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1392
3-cyanophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1393
4-cyanophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1394
2-nitrophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1395
3-nitrophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1396
4-nitrophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1397
2-trifluoromethylphenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1398
4-trifluoromethylphenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1399
4-trifluoromethoxyphenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1400
2,3-difluorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1401
2,4-difluorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1402
2,5-difluorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1403
2,6-difluorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1404
2,4-dichlorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1405
2,6-dichlorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1406
3,4-dichlorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1407
2-chloro-4-nitrophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1408
2-chloro-4-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1409
2-chloro-6-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1410
4-chloro-2-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1411
4-chloro-2-nitrophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1412
2,3,6-trifluorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1413
pyridin-2-yl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1414
pyridin-3-yl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1415
2-fluoropyridin-3-yl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1416
2-chloropyridin-3-yl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1417
2-chloropyridin-5-yl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1418
2-methylthiopyridin-3-yl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1419
pyrazin-2-yl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1420
furan-2-yl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1421
thiophen-2-yl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1422
phenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1423
2-methylphenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1424
4-methylphenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1425
2-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1426
3-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1427
4-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1428
2-chlorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1429
4-chlorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1430
2-bromophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1431
2-iodophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1432
3-cyanophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1433
4-cyanophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phneyl


1434
2-nitrophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1435
3-nitrophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1436
4-nitrophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1437
2-trifluoromethylphenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1438
4-trifluoromethylphenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1439
4-trifluoromethoxyphenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1440
2,3-difluorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1441
2,4-difluorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1442
2,5-difluorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1443
2,6-difluorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1444
2,4-dichlorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1445
2,6-dichlorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1446
3,4-dichlorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1447
2-chloro-4-nitrophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1448
2-chloro-4-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1449
2-chloro-6-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1450
4-chloro-2-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1451
4-chloro-2-nitrophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1452
2,3,6-trifluorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1453
pyridin-2-yl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1454
pyridin-3-yl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1455
2-fluoropyridin-3-yl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1456
2-chloropyridin-3-yl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1457
2-chloropyridin-5-yl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1458
2-methylthiopyridin-3-yl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1459
pyrazin-2-yl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1460
furan-2-yl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1461
thiophen-2-yl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1462
phenyl
Et
H
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1463
phenyl
Me
H
H
F
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1464
4-nitrophenyl
Me
H
H
F
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1465
4-cyanophenyl
Me
H
H
F
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1466
phenyl
Me
H
H
F
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1467
4-nitrophenyl
Me
H
H
F
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1468
4-cyanophenyl
Me
H
H
F
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl


1469
phenyl
Me
H
H
F
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1470
4-nitrophenyl
Me
H
H
F
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1471
4-cyanophenyl
Me
H
H
F
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1472
phenyl
Me
H
H
F
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1473
4-nitrophenyl
Me
H
H
F
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1474
4-cyanophenyl
Me
H
H
F
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1475
phenyl
Me
H
H
F
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


1476
4-nitrophenyl
Me
H
H
F
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


1477
4-cyanophenyl
Me
H
H
F
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


1478
phenyl
H
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1479
phenyl
H
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-6-methylphenyl


1480
phenyl
H
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1481
2-fluorophenyl
H
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1482
phenyl
H
Et
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1483
phenyl
H
i-Pr
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1484
phenyl
H
acetyl
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1485
phenyl
H
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1486
2-fluorophenyl
H
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1487
phenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1488
2-methylphenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1489
4-methylphenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1490
2-fluorophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1491
3-fluorophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1492
4-fluorophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1493
2-chlorophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1494
4-chlorophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1495
2-bromophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1496
iodophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1497
3-cyanophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1498
4-cyanophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1499
2-nitrophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1500
3-nitrophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1501
4-nitrophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1502
2-trifluoromethylphenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1503
4-trifluoromethylphenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1504
4-trifluoromethoxyphenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1505
2,3-difluorophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1506
2,4-difluorophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1507
2,5-difluorophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1508
2,6-difluorophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1509
2,4-dichlorophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1510
2,6-dichlorophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1511
3,4-dichlorophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1512
2-chloro-4-nitrophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1513
2-chloro-4-fluorophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1514
2-chloro-6-fluorophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1515
4-chloro-2-fluorophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1516
4-chloro-2-nitrophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1517
2,3,6-trifluorophenyl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1518
pyridin-2-yl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1519
pyridin-3-yl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1520
2-fluoropyridin-3-yl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1521
2-chloropyridin-3-yl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1522
2-chloropyridin-5-yl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1523
2-methylthiopyridin-3-yl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1524
pyrazin-2-yl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1525
furan-2-yl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1526
thiophen-2-yl
Me
Me
H
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1527
phenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1528
2-methylphenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1529
4-methylphenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1530
2-fluorophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1531
3-fluorophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1532
4-fluorophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1533
2-chlorophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1534
4-chlorophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1535
2-bromophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1536
2-iodophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1537
3-cyanophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1538
4-cyanophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1539
2-nitrophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1540
3-nitrophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1541
4-nitrophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1542
2-trifluoromethylphenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1543
4-trifluoromethylphenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1544
4-trifluoromethoxyphenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1545
2,3-difluorophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1546
2,4-difluorophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1547
2,5-difluorophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1548
2,6-difluorophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1549
2,4-dichlorophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1550
2,6-dichlorophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1551
3,4-dichlorophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1552
2-chloro-4-nitrophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1553
2-chloro-4-fluorophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1554
2-chloro-6-fluorophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1555
4-chloro-2-fluorophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1556
4-chloro-2-nitrophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1557
2,3,6-trifluorophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1558
pyridin-2-yl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1559
pyridin-3-yl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1560
2-fluoropyridin-3-yl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1561
2-chloropyridin-3-yl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1562
2-chloropyridin-5-yl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1563
2-methylthiopyridin-3-yl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1564
pyrazin-2-yl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1565
furan-2-yl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1566
thiophen-2-yl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1567
phenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1568
2-methylphenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1569
4-methylphenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1570
2-fluorophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1571
3-fluorophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1572
4-fluorophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1573
2-chlorophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1574
4-chlorophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1575
2-bromophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1576
2-iodophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1577
3-cyanophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1578
4-cyanophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1579
2-nitrophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1580
3-nitrophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1581
4-nitrophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1582
2-trifluoromethylphenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1583
4-trifluoromethylphenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1584
4-trifluoromethoxyphenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1585
2,3-difluorophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1586
2,4-difluorophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1587
2,5-difluorophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1588
2,6-difluorophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1589
2,4-dichlorophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1590
2,6-dichlorophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1591
3,4-dichlorophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1592
2-chloro-4-nitrophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1593
2-chloro-4-fluorophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1594
2-chloro-6-fluorophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1595
4-chloro-2-fluorophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1596
4-chloro-2-nitrophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1597
2,3,6-trifluorophenyl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1598
pyridin-2-yl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1599
pyridin-3-yl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1600
2-fluoropyridin-3-yl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1601
2-chloropyridin-3-yl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1602
2-chloropyridin-5-yl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1603
2-methylthiopyridin-3-yl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1604
pyrazin-2-yl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1605
furan-2-yl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1606
thiophen-2-yl
Me
Me
H
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1607
phenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1608
2-methylphenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1609
3-methylphenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1610
4-methylphenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1611
2-nitrophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1612
3-nitrophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1613
4-nitrophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1614
2-cyanophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1615
3-cyanophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1616
4-cyanophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1617
2-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1618
3-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1619
4-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1620
2-chlorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1621
4-chlorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1622
2-bromophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1623
2-iodophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1624
2-trifluoromethylphenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1625
4-trifluoromethylphenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1626
4-trifluoromethoxyphenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1627
2,3-difluorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1628
2.4-difluorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1629
2,5-difluorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1630
2,6-difluorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1631
2,4-dichlorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1632
2,6-dichlorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1633
3,4-dichlorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1634
2-fluoro-4-nitrophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1635
4-fluoro-2-nitrophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1636
2-chloro-4-fluorphenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1637
4-chloro-2-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1638
2-chloro-6-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1639
2-chloro-4-nitrophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1640
4-chloro-2-nitrophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1641
2,3,6-trifluorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1642
pyridin-2-yl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1643
pyridin-3-yl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1644
2-fluoropyridin-3-yl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1645
2-chloropyridin-3-yl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1646
2-chloropyridin-5-yl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1647
2-methylthiopyridin-3-yl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1648
pyrazin-2-yl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1649
furan-2-yl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1650
furan-3-yl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1651
2-tetrahydrofuranyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1652
benzofuran-2-yl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1653
thiophen-2-yl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1654
3,4-dinitrophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1655
3-methoxy-4-nitrophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1656
2,3,4-trifluorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1657
phenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1658
2-methylphenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1659
4-methylphenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1660
2-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1661
3-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1662
4-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1663
2-chlorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1664
4-chlorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1665
2-bromophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1666
2-iodophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1667
3-cyanophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1668
4-cyanophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1669
2-nitrophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1670
3-nitrophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1671
4-nitrophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1672
2-trifluoromethylphenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1673
4-trifluoromethylphenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1674
4-trifluoromethoxyphenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1675
2,3-difluorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1676
2,4-difluorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1677
2,5-difluorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1678
2,6-difluorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1679
2,4-dichlorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1680
2,6-dichlorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1681
3,4-dichlorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1682
2-chloro-4-nitrophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1683
2-chloro-4-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1684
2-chloro-6-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1685
4-chloro-2-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1686
4-chloro-2-nitrophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1687
2,3,6-trifluorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1688
pyridin-2-yl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1689
pyridin-3-yl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1690
2-fluoropyridin-3-yl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1691
2-chloropyridin-3-yl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1692
2-chloropyridin-5-yl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1693
2-methylthiopyridin-3-yl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1694
pyrazin-2-yl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1695
furan-2-yl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1696
thiophen-2-yl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1697
phenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1698
2-methylphenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1699
4-methylphenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1700
2-fluorophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1701
3-fluorophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1702
4-fluorophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1703
2-chlorophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1704
4-chlorophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1705
2-bromophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1706
2-iodophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1707
3-cyanophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1708
4-cyanophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1709
2-nitrophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1710
3-nitrophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1711
4-nitrophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1712
2-trifluoromethylphenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1713
4-trifluoromethylphenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1714
4-trifluoromethoxyphenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1715
2,3-difluorophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1716
2,4-difluorophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1717
2,5-difluorophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1718
2,6-difluorophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1719
2,4-dichlorophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1720
2,6-dichlorophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1721
3,4-dichlorophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1722
2-chloro-4-nitrophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1723
2-chloro-4-fluorophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1724
2-chloro-6-fluorophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1725
4-chloro-2-fluorophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1726
4-chloro-2-nitrophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1727
2,3,6-trifluorophenyl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1728
pyridin-2-yl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1729
pyridin-3-yl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1730
2-fluoropyridin-3-yl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1731
2-chloropyridin-3-yl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1732
2-chloropyridin-5-yl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1733
2-methylthiopyridin-3-yl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1734
pyrazin-2-yl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1735
furan-2-yl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1736
thiophen-2-yl
Me
Me
F
H
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl


1737
phenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1738
2-methylphenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1739
4-methylphenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1740
2-fluorophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1741
3-fluorophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1742
4-fluorophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1743
2-chlorophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1744
4-chlorophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1745
2-bromophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1746
2-iodophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1747
3-cyanophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1748
4-cyanophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1749
2-nitrophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1750
3-nitrophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1751
4-nitrophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1752
2-trifluoromethylphenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1753
4-trifluoromethylphenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1754
4-trifluoromethoxyphenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1755
2,3-difluorophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1756
2,4-difluorophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1757
2,5-difluorophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1758
2,6-difluorophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1759
2,4-dichlorophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1760
2,6-dichlorophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1761
3,4-dichlorophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1762
2-chloro-4-nitrophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1763
2-chloro-4-fluorophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1764
2-chloro-6-fluorophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1765
4-chloro-2-fluorophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1766
4-chloro-2-nitrophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1767
2,3,6-trifluorophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1768
pyridin-2-yl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1769
pyridin-3-yl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1770
2-fluoropyridin-3-yl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1771
2-chloropyridin-3-yl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1772
2-chloropyridin-5-yl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1773
2-methylthiopyridin-3-yl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1774
pyrazin-2-yl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1775
furan-2-yl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1776
thiophen-2-yl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(methylsulfonyl)phenyl


1777
phenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1778
2-methylphenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1779
4-methylphenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1780
2-fluorophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1781
3-fluorophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1782
4-fluorophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1783
2-chlorophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1784
4-chlorophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1785
2-bromophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1786
2-iodophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1787
3-cyanophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1788
4-cyanophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1789
2-nitrophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1790
3-nitrophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1791
4-nitrophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1792
2-trifluoromethylphenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1793
4-trifluoromethylphenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1794
4-trifluoromethoxyphenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1795
2,3-difluorophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1796
2,4-difluorophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1797
2,5-difluorophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1798
2,6-difluorophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1799
2,4-dichlorophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1800
2,6-dichlorophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1801
3,4-dichlorophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1802
2-chloro-4-nitrophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1803
2-chloro-4-fluorophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1804
2-chloro-6-fluorophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1805
4-chloro-2-fluorophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1806
4-chloro-2-nitrophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1807
2,3,6-trifluorophenyl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1808
pyridin-2-yl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1809
pyridin-3-yl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1810
2-fluoropyridin-3-yl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1811
2-chloropyridin-3-yl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1812
2-chloropyridin-5-yl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1813
2-methylthiopyridin-3-yl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1814
pyrazin-2-yl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1815
furan-2-yl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1816
thiophen-2-yl
Me
Me
F
H
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


1817
phenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1818
2-methylphenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1819
4-methylphenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1820
2-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1821
3-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1822
4-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1823
2-chlorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1824
4-chlorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1825
2-bromophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1826
2-iodophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1827
3-cyanophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1828
4-cyanophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1829
2-nitrophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1830
3-nitrophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1831
4-nitrophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1832
2-trifluoromethylphenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1833
4-trifluoromethylphenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1834
4-trifluoromethoxyphenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1835
2,3-difluorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1836
2,4-difluorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1837
2,5-difluorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1838
2,6-difluorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1839
2,4-dichlorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1840
2,6-dichlorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1841
3,4-dichlorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1842
2-chloro-4-nitrophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1843
2-chloro-4-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1844
2-chloro-6-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1845
4-chloro-2-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1846
4-chloro-2-nitrophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1847
2,3,6-trifluorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1848
pyridin-2-yl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1849
pyridin-3-yl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1850
2-fluoropyridin-3-yl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1851
2-chloropyridin-3-yl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1852
2-chloropyridin-5-yl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1853
2-methylthiopyridin-3-yl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1854
pyrazin-2-yl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1855
furan-2-yl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1856
thiophen-2-yl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


1857
phenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1858
2-methyphenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1859
4-methylphenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1860
2-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1861
3-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1862
4-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1863
2-chlorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1864
4-chlorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1865
2-bromophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1866
2-iodophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1867
3-cyanophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1868
4-cyanophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1869
2-nitrophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1870
3-nitrophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1871
4-nitrophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1872
2-trifluoromethylphenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1873
4-trifluoromethylphenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1874
4-trifluoromethoxyphenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1875
2,3-difluorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1876
2,4-difluorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1877
2,5-difluorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1878
2,6-difluorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1879
2,4-dichlorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1880
2,6-dichlorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1881
3,4-dichlorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1882
2-chloro-4-nitrophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1883
2-chloro-4-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1884
2-chloro-6-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1885
4-chloro-2-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1886
4-chloro-2-nitrophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1887
2,3,6-trifluorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1888
pyridin-2-yl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1889
pyridin-3-yl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1890
2-fluoropyridin-3-yl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1891
2-chloropyridin-3-yl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1892
2-chloropyridin-5-yl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1893
2-methylthiopyridin-3-yl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1894
pyrazin-2-yl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1895
furan-2-yl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1896
thiophen-2-yl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


1897
2-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(pentafluoroethyl)phenyl


1898
2-fluorophenyl
Me
H
H
H
2-bromo-4-heptafluoroisopropyl)-6-methylphenyl


1899
2-fluorophenyl
Me
H
H
H
2-ethyl-4-(heptafluoroisopropyl)-6-methylphenyl


1900
2-fluorophenyl
Me
H
H
H
4-(heptafluoroisopropyl)-2-iodo-6-methylphenyl


1901
2-fluorophenyl
Me
H
H
H
2-chloro-6-ethyl-4-(heptafluoroisopropyl)phenyl


1902
2-fluorophenyl
Me
H
H
H
2-bromo-6-ethyl-4-(heptafluoroisopropyl)phenyl


1903
2-fluorophenyl
Me
H
H
H
2-ethyl-4-(heptafluoroisopropyl)-6-iodophenyl


1904
2-fluorophenyl
Me
H
H
H
4-(heptafluoroisopropyl)-2-isopropyl-6-methylphenyl


1905
2-fluorophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-6-n-propylphenyl


1906
2-fluorophenyl
Me
H
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(trifluoromethylthio)phenyl


1907
2-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(trifluoromethylthio)phenyl


1908
2-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(pentafluoroethylthio)phenyl


1909
2-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(nonafluoro-n-butylthio)phenyl


1910
2-fluorophenyl
Me
H
H
H
2,6-dichloro-4-(heptafluoroisopropylsulfonyl)phenyl


1911
2-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


1912
2-fluorophenyl
Me
H
H
H
2-bromo-6-(heptafluoroisopropyloxy)-4-methylpyridin-








3-yl


1913
2-fluorophenyl
Me
H
H
H
2,4-dimethyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy)








pyridin-3-yl


1914
2-fluorophenyl
Me
H
H
H
2-chloro-4-methyl-6-(2,2,2-trifluoro-1-








trifluoromethylethoxy)pyridin-3-yl


1915
2-fluorophenyl
Me
H
H
H
2-bromo-4-methyl-6-(2,2,2-trifluoro-1-








trifluoromethylethoxy)pyridin-3-yl


1916
2-fluorophenyl
Me
H
H
H
2-iodo-4-methyl-6-(2,2,2-trifluoro-1-








trifluoromethylethoxy)pyridin-3-yl


1917
2-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(pentafluoroethyl)phenyl


1918
2-fluorophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-methylphenyl


1919
2-fluorophenyl
Me
H
F
H
2-ethyl-4-(heptafluoroisopropyl)-6-methylphenyl


1920
2-fluorophenyl
Me
H
F
H
4-(heptafluoroisopropyl)-2-iodo-6-methylphenyl


1921
2-fluorophenyl
Me
H
F
H
2-chloro-6-ethyl-4-(heptafluoroisopropyl)phenyl


1922
2-fluorophenyl
Me
H
F
H
2-bromo-6-ethyl-4-(heptafluoroisopropyl)phenyl


1923
2-fluorophenyl
Me
H
F
H
2-ethyl-4-(heptafluoroisopropyl)-6-iodophenyl


1924
2-fluorophenyl
Me
H
F
H
4-(heptafluoroisopropyl)-2-isopropyl-6-methylphenyl


1925
2-fluorophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-6-n-propylphenyl


1926
2-fluorophenyl
Me
H
F
H
2-bromo-4-(heptafluoroisopropyl)-








6-(trifluoromethylthio)phenyl


1927
2-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(trifluoromethylthio)phenyl


1928
2-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(pentafluoroethylthio)phenyl


1929
2-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(nonafluoro-n-butylthio)phenyl


1930
2-fluorophenyl
Me
H
F
H
2,6-dichloro-4-(heptafluoroisopropylsulfonyl)phenyl


1931
2-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


1932
2-fluorophenyl
Me
H
F
H
2-bromo-6-(heptafluoroisopropyloxy)-








4-methylpyridin-3-yl


1933
2-fluorophenyl
Me
H
F
H
2,4-dimethyl-6-(2,2,2-trifluoro-








1-trifluoromethylethoxy)pyridin-3-yl


1934
2-fluorophenyl
Me
H
F
H
2-chloro-4-methyl-6-(2,2,2-trifluoro-








1-trifluoromethylethoxy)pyridin-3-yl


1935
2-fluorophenyl
Me
H
F
H
2-bromo-4-methyl-6-(2,2,2-trifluoro-








1-trifluoromethylethoxy)pyridin-3-yl


1936
2-fluorophenyl
Me
H
F
H
2-iodo-4-methyl-6-(2,2,2-trifluoro-








1-trifluoromethylethoxy)pyridin-3-yl


1937
2-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(pentafluoroethyl)phenyl


1938
2-fluorophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-6-methylphenyl


1939
2-fluorophenyl
Me
Me
H
H
2-ethyl-4-(heptafluoroisopropyl)-6-methylphenyl


1940
2-fluorophenyl
Me
Me
H
H
4-(heptafluoroisopropyl)-2-iodo-6-methylphenyl


1941
2-fluorophenyl
Me
Me
H
H
2-chloro-6-ethyl-4-(heptafluoroisopropyl)phenyl


1942
2-fluorophenyl
Me
Me
H
H
2-bromo-6-ethyl-4-(heptafluoroisopropyl)phenyl


1943
2-fluorophenyl
Me
Me
H
H
2-ethyl-4-(heptafluoroisopropyl)-6-iodophenyl


1944
2-fluorophenyl
Me
Me
H
H
4-(heptafluoroisopropyl)-2-isopropyl-6-methylphenyl


1945
2-fluorophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-6-n-propylphenyl


1946
2-fluorophenyl
Me
Me
H
H
2-bromo-4-(heptafluoroisopropyl)-








6-(trifluoromethylthio)phenyl


1947
2-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(trifluoromethylthio)phenyl


1948
2-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(pentafluoroethylthio)phenyl


1949
2-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(nonafluoro-n-butylthio)phenyl


1950
2-fluorophenyl
Me
Me
H
H
2,6-dichloro-4-(heptafluoroisopropylsulfonyl)phenyl


1951
2-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


1952
2-fluorophenyl
Me
Me
H
H
2-bromo-6-(heptafluoroisopropyloxy)-








4-methylpyridin-3-yl


1953
2-fluorophenyl
Me
Me
H
H
2,4-dimethyl-6-(2,2,2-trifluoro-








1-trifluoromethylethoxy)pyridin-3-yl


1954
2-fluorophenyl
Me
Me
H
H
2-chloro-4-methyl-6-(2,2,2-trifluoro-








1-trifluoromethylethoxy)pyridin-3-yl


1955
2-fluorophenyl
Me
Me
H
H
2-bromo-4-methyl-6-(2,2,2-trifluoro-








1-trifluoromethylethoxy)pyridin-3-yl


1956
2-fluorophenyl
Me
Me
H
H
2-iodo-4-methyl-6-(2,2,2-trifluoro-








1-trifluoromethylethoxy)pyridin-3-yl


1957
2-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(pentafluoroethyl)phenyl


1958
2-fluorophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-6-methylphenyl


1959
2-fluorophenyl
Me
Me
F
H
2-ethyl-4-(heptafluoroisopropyl)-6-methylphenyl


1960
2-fluorophenyl
Me
Me
F
H
4-(heptafluoroisopropyl)-2-iodo-6-methylphenyl


1961
2-fluorophenyl
Me
Me
F
H
2-chloro-6-ethyl-4-(heptafluoroisopropyl)phenyl


1962
2-fluorophenyl
Me
Me
F
H
2-bromo-6-ethyl-4-(heptafluoroisopropyl)phenyl


1963
2-fluorophenyl
Me
Me
F
H
2-ethyl-4-(heptafluoroisopropyl)-6-iodophenyl


1964
2-fluorophenyl
Me
Me
F
H
4-(heptafluoroisopropyl)-2-isopropyl-6-methylphenyl


1965
2-fluorophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-6-n-propylphenyl


1966
2-fluorophenyl
Me
Me
F
H
2-bromo-4-(heptafluoroisopropyl)-6-








(trifluoromethylthio)phenyl


1967
2-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(trifluoromethylthio)phenyl


1968
2-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(pentafluoroethylthio)phenyl


1969
2-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(nonafluoro-n-butylthio)phenyl


1970
2-fluorophenyl
Me
Me
F
H
2,6-dichloro-4-(heptafluoroisopropylsulfonyl)phenyl


1971
2-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl


1972
2-fluorophenyl
Me
Me
F
H
2-bromo-6-(heptafluoroisopropyloxy)-4-methylpyridin-3-yl


1973
2-fluorophenyl
Me
Me
F
H
2,4-dimethyl-6-(2,2,2-trifluoro-








1-trifluoromethylethoxy)pyridin-3-yl


1974
2-fluorophenyl
Me
Me
F
H
2-chloro-4-methyl-6-(2,2,2-trifluoro-








1-trifluoromethylethoxy)pyridin-3-yl


1975
2-fluorophenyl
Me
Me
F
H
2-bromo-4-methyl-6-(2,2,2-trifluoro-








1-trifluoromethylethoxy)pyridin-3-yl


1976
2-fluorophenyl
Me
Me
F
H
2-iodo-4-methyl-6-(2,2,2-trifluoro-








1-trifluoromethylethoxy)pyridin-3-yl
















TABLE 4









embedded image

















Comp. No.
Q1
R1
A1
A2
Q2





2001
phenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2002
2-methylphenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2003
4-methylphenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2004
2-fluorophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2005
3-fluorophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2006
4-fluorophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2007
2-chlorophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2008
4-chlorophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2009
2-bromophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2010
2-iodophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2011
3-cyanophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2012
4-cyanophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2013
2-nitrophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2014
3-nitrophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2015
4-nitrophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2016
2-trifluoromethylphenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2017
4-trifluoromethylphenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2018
4-trifluoromethoxyphenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2019
2,3-difluorophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2020
2,4-difluorophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2021
2,5-difluorophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2022
2,6-difluorophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2023
2,4-dichlorophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2024
2,6-dichlorophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2025
3,4-dichlorophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2026
2-chloro-4-nitrophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2027
2-chloro-4-fluorophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2028
2-chloro-6-fluorophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2029
4-chloro-2-fluorophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2030
4-chloro-2-nitrophenyl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2031
2,3,6-trifluoro-
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl



phenyl






2032
pyridin-2-yl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2033
pyridin-3-yl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2034
pyridin-4-yl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2035
2-fluoropyridin-3-yl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2036
2-chloropyridin-3-yl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2037
2-chloropyridin-5-yl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2038
2-methylthiopyridin-
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl



3-yl






2039
pyrazin-2-yl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2040
furan-2-yl
H
N
C
2, 6-dimethyl-4-heptafluoroisopropylphenyl


2041
thiophen-2-yl
H
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2042
phenyl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2043
2-methylphenyl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2044
4-methylphenyl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2045
2-fluorophenyl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2046
3-fluorophenyl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2047
4-fluorophenyl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2048
2-chlorophenyl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2049
4-chlorophenyl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2050
2-bromophenyl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthi0)phenyl


2051
2-iodophenyl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2052
3-cyanophenyl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2053
4-cyanophenyl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2054
2-nitrophenyl
H
N
C
2,6-dibromo-4-(heptafiuoro-n-propylthio)phenyl


2055
3-nitrophenyl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2056
4-nitrophenyl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2057
2-trifluoromethyl-
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



phenyl






2058
4-trifluoromethyl-
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



phenyl






2059
4-trifluoromethoxy-
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



phenyl






2060
2,3-difluorophenyl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2061
2,4-difluorophenyl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2062
2,5-difluorophenyl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2063
2,6-difluorophenyl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2064
2,4-dichlorophenyl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2065
2,6-dichlorophenyl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2066
3,4-dichlorophenyl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2067
2-chloro-4-nitro-
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



phenyl






2068
2-chloro-4-fluoro-
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



phenyl






2069
2-chloro-6-fluoro-
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



phenyl






2070
4-chloro-2-fluoro-
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



phenyl






2071
4-chloro-2-nitro-
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



phenyl






2072
2,3,6-trifluoro-
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



phenyl






2073
pyridin-2-yl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2074
pyridin-3-yl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2075
2-fluoropyridin-
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



3-yl






2076
2-chloropyridin-3-yl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2077
2-chloropyridin-5-yl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2078
2-methylthiopyridin-
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



3-yl






2079
pyrazin-2-yl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2080
furan-2-yl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2081
thiophen-2-yl
H
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2082
phenyl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2083
2-methylphenyl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2084
4-methylphenyl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2085
2-fluorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2086
3-fluorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2087
4-fluorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2088
2-chlorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2089
4-chlorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2090
2-bromophenyl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2091
2-iodophenyl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2092
3-cyanophenyl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2093
4-cyanophenyl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2094
2-nitrophenyl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2095
3-nitrophenyl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2096
4-nitrophenyl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2097
2-trifluoromethyl-
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl



phenyl






2098
4-trifluoromethyl-
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl



phenyl






2099
4-trifluoromethoxy-
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl



phenyl






2100
2,3-difluorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2101
2,4-difluorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2102
2,5-difluorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2103
2,6-difluorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2104
2,4-dichlorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2105
2,6-dichlorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2106
3,4-dichlorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2107
2-chloro-4-nitro-
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl



phenyl






2108
2-chloro-4-fluoro-
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl



phenyl






2109
2-chloro-6-fluoro-
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl



phenyl






2110
4-chloro-2-fluoro-
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl



phenyl






2111
4-chloro-2-nitro-
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl



phenyl






2112
2,3,6-trifluoro-
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl



phenyl






2113
pyridin-2-yl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2114
pyridin-3-yl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2115
2-fluoropyridin-3-yl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2116
2-ch1oropyridin-3-yl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2117
2-chloropyridin-5-yl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2118
2-methylthiopyridin-
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl



3-yl






2119
pyrazin-2-yl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2120
furan-2-yl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2121
thiophen-2-yl
Me
N
C
2,6-dimethyl-4-heptafluoroisopropylPhenyl


2122
phenyl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2123
2-methylphenyl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2124
4-methylphenyl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2125
2-fluorophenyl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2126
3-fluorophenyl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2127
4-fluorophenyl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2128
2-chlorophenyl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2129
4-chlorophenyl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2130
2-bromophenyl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2131
2-iodophenyl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2132
3-cyanophenyl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2133
4-cyanophenyl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2134
2-nitrophenyl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2135
3-nitrophenyl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2136
4-nitrophenyl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2137
2-trifluoromethyl-
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



phenyl






2138
4-trifluoromethyl-
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



phenyl






2139
4-trifluoromethoxy-
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



phenyl






2140
2,3-difluorophenyl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2141
2,4-difluorophenyl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2142
2,5-difluorophenyl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2143
2,6-difluorophenyl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2144
2,4-dichlorophenyl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2145
2,6-dichlorophenyl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2146
3,4-dichlorophenyl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2147
2-chloro-4-nitro-
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



phenyl






2148
2-chloro-4-fluoro-
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



phenyl






2149
2-chloro-6-fluoro-
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



phenyl






2150
4-chloro-2-fluoro-
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



phenyl






2151
4-chloro-2-nitro-
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



phenyl






2152
2,3,6-trifluoro-
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



phenyl






2153
pyridin-2-yl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2154
pyridin-3-yl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2155
2-fluoropyridin-
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



3-yl






2156
2-chloropyridin-3-
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



yl






2157
2-chloropyridin-5-
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



yl






2158
2-methylthiopyridin-
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl



3-yl






2159
pyrazin-2-yl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2160
furan-2-yl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2161
thiophen-2-yl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2162
phenyl
H
C
N
2,6-dimethyl-4-heptafluoroisopropylphenyl


2163
phenyl
H
C
N-oxide
2,6-dimethyl-4-heptafluoroisopropylphenyl


2164
phenyl
H
N-oxide
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2165
2-fluorophenyl
H
N-oxide
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2166
phenyl
H
N-oxide
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2167
2-fluorophenyl
H
N-oxide
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2168
phenyl
Me
N-oxide
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2169
2-fluorophenyl
Me
N-oxide
C
2,6-dimethyl-4-heptafluoroisopropylphenyl


2170
phenyl
Me
N-oxide
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2171
2-fluorophenyl
Me
N-oxide
C
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl
















TABLE 5









embedded image















Comp.





No.
G1
G2
Q2





2201
O
S
2,6-dimethyl-4-heptafluoroisopropylphenyl


2202
S
O
2,6-dimethyl-4-heptafluoroisopropylphenyl


2203
S
S
2,6-dimethyl-4-heptafluoroisopropylphenyl


2204
O
S
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2205
S
O
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2206
S
S
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl


2207
O
S
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


2208
S
O
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


2209
S
S
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl


2210
O
S
2-bromo-4-(heptafluoroisopropyl)-6-





(methylsulfonyl)phenyl


2211
S
O
2-bromo-4-(heptafluoroisopropyl)-6-





(methylsulfonyl)phenyl


2212
S
S
2-bromo-4-(heptafluoroisopropyl)-6-





(methylsulfonyl)phenyl


2213
O
S
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


2214
S
O
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)phenyl


2215
S
S
2-n-propyl-6-iodo-4-(heptafluoroisopropyl)Phenyl


2216
O
S
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


2217
S
O
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


2218
S
S
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl


2219
O
S
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl


2220
S
O
2,6-dich1oro-4-(heptafluoro-n-propylthio)phenyl


2221
S
S
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl
















TABLE 6









embedded image



















Comp.









No.
R1
R2
Y1
Y2
Y3
Y4
Y5





I-1
H
H
Me
H
heptafluoro-n-propyl
H
Me


I-2
H
H
Me
H
heptafluoroisopropyl
H
Me


I-3
H
H
Me
Me
heptafluoroisopropyl
H
Cl


I-4
H
H
Me
I
heptafluoroisopropyl
H
Cl


I-5
H
Me
Me
H
heptafluoroisopropyl
H
Me


I-6
H
i-Pr
Me
H
heptafluoroisopropyl
H
Me


I-7
H
H
Et
H
heptafluoroisopropyl
H
Me


I-8
H
H
Et
H
heptafluoroisopropyl
H
Et


I-9
H
H
Et
H
heptafluoroisopropyl
H
I


I-10
H
H
i-Pr
H
heptafluoroisopropyl
H
Me


I-11
H
H
MeO
H
heptafluoroisopropyl
H
Me


I-12
H
H
Cl
H
heptafluoroisopropyl
H
Et


I-13
H
H
Cl
Me
heptafluoroisopropyl
H
Me


I-14
H
H
Br
H
heptafluoroisopropyl
H
Me


I-15
H
H
Br
H
heptafluoroisopropyl
H
Et


I-16
H
H
Br
H
heptafluoroisopropyl
H
n-Pr


I-17
H
H
Br
H
heptafluoroisopropyl
H
n-Bu


I-18
H
H
Br
Me
heptafluoroisopropyl
H
Me


I-19
H
H
I
H
heptafluoroisopropyl
H
Me


I-20
H
H
I
H
heptafluoroisopropyl
H
n-Pr


I-21
H
H
Me
H
nonafluoto-n-butyl
H
Me


I-22
H
H
Me
H
nonafluoto-2-butyl
H
Me


I-23
H
H
Br
H
trifluoromethylthio
H
Br


I-24
H
H
Br
H
trifluoromethylsulfonyl
H
Br


I-25
H
H
Cl
H
heptafluoroisopropylthio
H
Cl


I-26
H
H
Br
H
heptafluoroisopropylthio
H
Br


I-27
H
H
Cl
H
heptafluoro-n-propylthio
H
Cl


I-28
H
H
Br
H
heptafluoro-n-propylthio
H
Br


I-29
H
H
Cl
H
heptafluoroisopropylsulfonyl
H
Cl


I-30
H
H
Br
H
nonafluoto-n-butylthio
H
Br


I-31
H
H
Br
H
pentafluoroethylthio
H
Br


I-32
H
H
Br
H
heptafluoro-n-propylsulfinyl
H
Br


I-33
Me
H
Me
H
heptafluoro-n-propylthio
H
Me


I-34
H
Me
Br
H
heptafluoro-n-propylthio
H
Br


I-35
H
H
Cl
H
heptafluoroisopropyl
H
n-Bu


I-36
H
H
I
H
heptafluoroisopropyl
H
n-Bu


I-37
H
H
Br
H
pentafluoroethyl
H
Br


I-38
H
H
Cl
H
heptafluoroisopropyl
H
s-Bu


I-39
H
H
I
H
heptafluoroisopropyl
H
s-Bu


I-40
H
H
Br
H
heptafluoroisopropyl
H
Br


I-41
H
H
Cl
H
pentafluoroethyl
H
Cl


I-42
H
H
Br
H
heptafluoroisopropyl
H
MeSO2


I-43
Me
H
Br
H
heptafluoroisopropyl
H
MeSO2


I-44
Me
Me
Br
H
heptafluoroisopropyl
H
MeSO2


I-45
H
H
Br
H
heptafluoroisopropyl
H
MeSO


I-46
Me
H
Br
H
heptafluoroisopropyl
H
MeSO


I-47
Me
Me
Br
H
heptafluoroisopropyl
H
MeSO


I-48
H
H
Br
H
heptafluoroisopropyl
H
MeS


I-49
Me
H
Br
H
heptafluoroisopropyl
H
MeS


I-50
Me
Me
Br
H
heptafluoroisopropyl
H
MeS


I-51
Me
Me
Me
H
heptafluoroisopropyl
H
Me


I-52
Me
Me
Me
H
nonafluoto-2-butyl
H
Me


I-53
Me
H
I
H
heptafluoroisopropyl
H
n-Pr


I-54
Me
Me
I
H
heptafluoroisopropyl
H
n-Pr


I-55
Me
Me
Br
H
heptafluoro-n-propylthio
H
Br


I-56
Me
H
Br
H
heptafluoro-n-propylthio
H
Br


I-57
H
H
Br
H
heptafluoro-n-propylsulfinyl
H
Br


I-58
Me
H
Br
H
heptafluoro-n-propylsulfinyl
H
Br


I-59
Me
Me
Br
H
heptafluoro-n-propylsulfinyl
H
Br


I-60
H
H
Br
H
heptafluoro-n-propylsulfonyl
H
Br


I-61
Me
H
Br
H
heptafluoro-n-propylsulfonyl
H
Br


I-62
Me
Me
Br
H
heptafluoro-n-propylsulfonyl
H
Br


I-63
Me
Me
Cl
H
heptafluoro-n-propylthio
H
Cl


I-64
Me
H
Cl
H
heptafluoro-n-propylthio
H
Cl


I-65
H
H
Cl
H
heptafluoro-n-propylsulfinyl
H
Cl


I-66
Me
H
Cl
H
heptafluoro-n-propylsulfinyl
H
Cl


I-67
Me
Me
Cl
H
heptafluoro-n-propylsulfinyl
H
Cl


I-68
H
H
Cl
H
heptafluoro-n-propylsulfonyl
H
Cl


I-69
Me
H
Cl
H
heptafluoro-n-propylsulfonyl
H
Cl


I-70
Me
Me
Cl
H
heptafluoro-n-propylsulfonyl
H
Cl
















TABLE 7









embedded image





















Comp. No.
X1
X2
X3
X4
R1
R2
Y1
Y3
Y5





I-81
Me
H
H
H
H
H
Me
heptafluoroisopropyl
Me


I-82
H
Me
H
H
H
H
Me
heptafluoroisopropyl
Me


I-83
H
H
H
Me
H
H
Me
heptafluoroisopropyl
Me


I-84
F
H
H
H
H
H
Me
heptafluoroisopropyl
Me


I-85
F
H
H
H
H
H
Me
heptafluoroisopropylthio
Me


I-86
H
F
H
H
H
H
Me
heptafluoroisopropyl
Me


I-87
H
H
H
F
H
H
Me
heptafluoroisopropyl
Me


I-88
Cl
H
H
H
H
H
Me
heptafluoroisopropyl
Me


I-89
H
Cl
H
H
H
H
Me
heptafluoroisopropyl
Me


I-90
H
H
H
Cl
H
H
Me
heptafluoroisopropyl
Me


I-91
Br
H
H
H
H
H
Me
heptafluoroisopropyl
Me


I-92
H
H
H
I
H
H
Me
heptafluoroisopropyl
Me


I-93
H
H
CF3
H
H
H
Me
heptafluoroisopropyl
Me


I-94
F
H
H
H
H
Me
Me
heptafluoroisopropyl
Me


I-95
F
H
H
H
Me
H
Me
heptafluoroisopropyl
Me


I-96
F
H
H
H
Me
Me
Me
heptafluoroisopropyl
Me


I-97
F
H
H
H
H
Me
Me
nonafluoto-2-butyl
Me


I-98
F
H
H
H
Me
H
Me
nonafluoto-2-butyl
Me


I-99
F
H
H
H
Me
Me
Me
nonafluoto-2-butyl
Me


I-100
F
H
H
H
H
Me
Br
heptafluoro-n-propylthio
Br


I-101
F
H
H
H
Me
H
Br
heptafluoro-n-propylthio
Br


I-102
F
H
H
H
Me
Me
Br
heptafluoro-n-propylthio
Br


I-103
F
H
H
H
H
Me
Br
heptafluoro-n-propylsulfinyl
Br


I-104
F
H
H
H
Me
H
Br
heptafluoro-n-propylsulfinyl
Br


I-105
F
H
H
H
Me
Me
Br
heptafluoro-n-propylsulfinyl
Br


I-106
F
H
H
H
H
Me
n-Pr
heptafluoroisopropyl
I


I-107
F
H
H
H
Me
H
n-Pr
heptafluoroisopropyl
I


I-108
F
H
H
H
Me
Me
n-Pr
heptafluoroisopropyl
I


I-109
F
H
H
H
H
Me
Br
heptafluoroisopropyl
MeSO2


I-110
F
H
H
H
Me
H
Br
heptafluoroisopropyl
MeSO2


I-111
F
H
H
H
Me
Me
Br
heptafluoroisopropyl
MeSO2


I-112
F
H
H
H
H
Me
Br
heptafluoroisopropyl
MeSO


I-113
F
H
H
H
Me
H
Br
heptafluoroisopropyl
MeSO


I-114
F
H
H
H
Me
Me
Br
heptafluoroisopropyl
MeSO
















TABLE 8









embedded image

















Comp. No.
X1a
R2a
Ra
Rb
Rc





I-121
H
H
CF3
F
OH


I-122
H
H
CF3
F
Cl


I-123
H
H
CF3
F
Br


I-124
H
H
CF3
CF3
OH


I-125
H
H
CF3
CF3
Cl


I-126
H
H
CF3
CF3
Br


I-127
H
H
CF3
C2F5
OH


I-128
H
H
CF3
C2F5
Cl


I-129
H
H
CF3
C2F5
Br


I-130
F
H
CF3
F
OH


I-131
F
H
CF3
F
Cl


I-132
F
H
CF3
F
Br


I-133
F
H
CF3
CF3
OH


I-134
F
H
CF3
CF3
Cl


I-135
F
H
CF3
CF3
Br


I-136
F
H
CF3
C2F5
OH


I-137
F
H
CF3
C2F5
Cl


I-138
F
H
CF3
C2F5
Br


I-139
Cl
H
CF3
F
OH


I-140
Cl
H
CF3
F
Cl


I-141
Cl
H
CF3
F
Br


I-142
Cl
H
CF3
CF3
OH


I-143
Cl
H
CF3
CF3
Cl


I-144
Cl
H
CF3
CF3
Br


I-145
Cl
H
CF3
C2F5
OH


I-146
Cl
H
CF3
C2F5
Cl


I-147
Cl
H
CF3
C2F5
Br


I-148
H
Me
CF3
F
OH


I-149
H
Me
CF3
F
Cl


I-150
H
Me
CF3
F
Br


I-151
H
Me
CF3
CF3
OH


I-152
H
Me
CF3
CF3
Cl


I-153
H
Me
CF3
CF3
Br


I-154
H
Me
CF3
C2F5
OH


I-155
H
Me
CF3
C2F5
Cl


I-156
H
He
CF3
C2F5
Br


I-157
F
Me
CF3
F
OH


I-158
F
Me
CF3
F
Cl


I-159
F
Me
CF3
F
Br


I-160
F
Me
CF3
CF3
OH


I-161
F
Me
CF3
CF3
Cl


I-162
F
He
CF3
CF3
Br


I-163
F
Me
CF3
C2F5
OH


I-164
F
Me
CF3
C2F5
Cl


I-165
F
Me
CF3
C2F5
Br


I-166
Cl
Me
CF3
F
OH


I-167
Cl
Me
CF3
F
Cl


I-168
Cl
Me
CF3
F
Br


I-169
Cl
Me
CF3
CF3
OH


I-170
Cl
Me
CF3
CF3
Cl


I-171
Cl
Me
CF3
CF3
Br


I-172
Cl
Me
CF3
C2F5
OH


I-173
Cl
Me
CF3
C2F5
Cl


I-174
Cl
Me
CF3
C2F5
Br
















TABLE 9









embedded image


















Comp. No.
X1a
R1a
R2a
Ra
Rb
Rc





I-201
H
H
H
CF3
F
OH


I-202
H
H
H
CF3
F
Cl


I-203
H
H
H
CF3
F
Br


I-204
H
H
H
CF3
CF3
OH


I-205
H
H
H
CF3
CF3
Cl


I-206
H
H
H
CF3
CF3
Br


I-207
H
H
H
CF3
C2F5
OH


I-208
H
H
H
CF3
C2F5
Cl


I-209
H
H
H
CF3
C2F5
Br


I-210
F
H
H
CF3
F
OH


I-211
F
H
H
CF3
F
Cl


I-212
F
H
H
CF3
F
Br


I-213
F
H
H
CF3
CF3
OH


I-214
F
H
H
CF3
CF3
Cl


I-215
F
H
H
CF3
CF3
Br


I-216
F
H
H
CF3
C2F5
OH


I-217
F
H
H
CF3
C2F5
Cl


I-218
F
H
H
CF3
C2F5
Br


I-219
Cl
H
H
CF3
F
OH


I-220
Cl
H
H
CF3
F
Cl


I-221
Cl
H
H
CF3
F
Br


I-222
Cl
H
H
CF3
CF3
OH


I-223
Cl
H
H
CF3
CF3
Cl


I-224
Cl
H
H
CF3
CF3
Br


I-225
Cl
H
H
CF3
C2F5
OH


I-226
Cl
H
H
CF3
C2F5
Cl


I-227
Cl
H
H
CF3
C2F5
Br


I-228
H
H
Me
CF3
F
OH


I-229
H
H
Me
CF3
F
Cl


I-230
H
H
Me
CF3
F
Br


I-231
H
H
Me
CF1
CF3
OH


I-232
H
H
Me
CF3
CF3
Cl


I-233
H
H
Me
CF3
CF3
Br


I-234
H
H
Me
CF3
C2F5
OH


I-235
H
H
Me
CF3
C2F5
Cl


I-236
H
H
Me
CF3
C2F5
Br


I-237
F
H
Me
CF3
F
OH


I-238
F
H
Me
CF3
F
Cl


I-239
F
H
Me
CF3
F
Br


I-240
F
H
Me
CF3
CF3
OH


I-241
F
H
Me
CF3
CF3
Cl


I-242
F
H
Me
CF3
CF3
Br


I-243
F
H
He
CF3
C2F5
OH


I-244
F
H
Me
CF3
C2F5
Cl


I-245
F
H
Me
CF3
C2F5
Br


I-246
Cl
H
Me
CF3
F
OH


I-247
Cl
H
Me
CF3
F
Cl


I-248
Cl
H
Me
CF3
F
Br


I-249
Cl
H
Me
CF3
CF3
OH


I-250
Cl
H
Me
CF3
CF3
Cl


I-251
Cl
H
Me
CF3
CF3
Br


I-252
Cl
H
Me
CF3
C2F5
OH


I-253
Cl
H
Me
CF3
C2F5
Cl


I-254
Cl
H
Me
CF3
C2F5
Br


I-255
H
Me
H
CF3
F
OH


I-256
H
Me
H
CF3
F
Cl


I-257
H
Me
H
CF3
F
Br


I-258
H
Me
H
CF3
CF3
OH


I-259
H
Me
H
CF3
CF3
Cl


I-260
H
Me
H
CF3
CF3
Br


I-261
H
Me
H
CF3
C2F5
OH


I-262
H
Me
H
CF3
C2F5
Cl


I-263
H
Me
H
CF3
C2F5
Br


I-264
F
Me
H
CF3
F
OH


I-265
F
Me
H
CF3
F
Cl


I-266
F
Me
H
CF3
F
Br


I-267
F
Me
H
CF3
CF3
OH


I-268
F
Me
H
CF3
CF3
Cl


I-269
F
Me
H
CF3
CF3
Br


I-270
F
Me
H
CF3
C2F5
OH


I-271
F
Me
H
CF3
C2F5
Cl


I-272
F
Me
H
CF3
C2F5
Br


I-273
Cl
Me
H
CF3
F
OH


I-274
Cl
Me
H
CF3
F
Cl


I-275
Cl
Me
H
CF3
F
Br


I-276
Cl
Me
H
CF3
CF3
OH


I-277
Cl
Me
H
CF3
CF3
Cl


I-278
Cl
Me
H
CF3
CF3
Br


I-279
Cl
Me
H
CF3
C2F5
OH


I-280
Cl
Me
H
CF3
C2F5
Cl


I-281
Cl
Me
H
CF3
C2F5
Br


I-282
11
Me
Me
CF3
F
OH


I-283
H
Me
Me
CF3
F
Cl


I-284
H
Me
Me
CF3
F
Br


I-285
H
Me
Me
CF3
CF3
OH


I-286
H
Me
Me
CF3
CF3
Cl


I-287
H
Me
Me
CF3
CF3
Br


I-288
H
Me
Me
CF3
C2F5
OH


I-289
H
Me
Me
CF3
C2F5
Cl


I-290
H
Me
Me
CF3
C2F5
Br


I-291
F
Me
Me
CF3
F
OH


I-292
F
Me
Me
CF3
F
Cl


I-293
F
Me
Me
CF3
F
Br


I-294
F
Me
Me
CF3
CF3
OH


I-295
F
Me
Me
CF3
CF3
Cl


I-296
F
Me
Me
CF3
CF3
Br


I-297
F
Me
Me
CF3
C2F5
OH


I-298
F
Me
Me
CF3
C2F5
Cl


I-299
F
Me
Me
CF3
C2F5
Br


I-300
Cl
Me
Me
CF3
F
OH


I-301
Cl
Me
Me
CF3
F
Cl


I-302
Cl
Me
Me
CF3
F
Br


I-303
Cl
Me
Me
CF3
CF3
OH


I-304
Cl
Me
Me
CF3
CF3
Cl


I-305
Cl
Me
Me
CF3
CF3
Br


I-306
Cl
Me
Me
CF3
C2F5
OH


I-307
Cl
Me
Me
CF3
C2F5
Cl


I-308
Cl
Me
Me
CF3
C2F5
Br
















TABLE 10









embedded image




















Comp. No.
Q1a
X1a
R1a
R2a
Y1a
Y5a
Rb
Rb





I-351
phenyl
H
H
H
H
H
CF3
OH


I-352
2-methylphenyl
H
H
H
H
H
CF3
OH


I-353
3-methylphenyl
H
H
H
H
H
CF3
OH


I-354
4-methylphenyl
H
H
H
H
H
CF3
OH


I-355
2,3-dimethylphenyl
H
H
H
H
H
CF3
OH


I-356
2,4,6-trimethylphenyl
H
H
H
H
H
CF3
OH


I-357
4-ethylphenyl
H
H
H
H
H
CF3
OH


I-358
2-fluorophenyl
H
H
H
H
H
CF3
OH


I-359
3-fluorophenyl
H
H
H
H
H
CF3
OH


I-360
4-fluorophenyl
H
H.
H
H
H
CF3
OH


I-361
2-chlorophenyl
H
H
H
H
H
CF3
OH


I-362
3-chlorophenyl
H
H
H
H
H
CF3
OH


I-363
4-chlorophenyl
H
H
H
H
H
CF3
OH


I-364
2-bromophenyl
H
H
H
H
H
CF3
OH


I-365
4-bromophenyl
H
H
H
H
H
CF3
OH


I-366
2-iodophenyl
H
H
H
H
H
CF3
OH


I-367
3-iodophenyl
H
H
H
H
H
CF3
OH


I-368
4-iodophenyl
H
H
H
H
H
CF3
OH


I-369
3-cyanophenyl
H
H
H
H
H
CF3
OH


I-370
4-cyanophenyl
H
H
H
H
H
CF3
OH


I-371
2-nitrophenyl
H
H
H
H
H
CF3
OH


I-372
3-nitrophenyl
H
H
H
H
H
CF3
OH


I-373
4-nitrophenyl
H
H
H
H
H
CF3
OH


I-374
2-trifluoromethylphenyl
H
H
H
H
H
CF3
OH


I-375
4-trifluoromethylphenyl
H
H
H
H
H
CF3
OH


I-376
4-trifluoromethoxyphenyl
H
H
H
H
H
CF3
OH


I-377
2,3-difluorophenyl
H
H
H
H
H
CF3
OH


I-378
2,4-difluorophenyl
H
H
H
H
H
CF3
OH


I-379
2,5-difluorophenyl
H
H
H
H
H
CF3
OH


I-380
2,6-difluorophenyl
H
H
H
H
H
CF3
OH


I-381
2,4-dichlorophenyl
H
H
H
H
H
CF3
OH


I-382
2,6-dichlorophenyl
H
H
H
H
H
CF3
OH


I-383
3,4-dichlorophenyl
H
H
H
H
H
CF3
OH


I-384
4-fluoro-3-nitrophenyl
H
H
H
H
H
CF3
OH


I-385
5-fluoro-2-nitrophenyl
H
H
H
H
H
CF3
OH


I-386
2-chloro-4-nitrophenyl
H
H
H
H
H
CF3
OH


I-387
2-chloro-4-fluorophenyl
H
H
H
H
H
CF3
OH


I-388
3-chloro-4-fluorophenyl
H
H
H
H
H
CF3
OH


I-389
2-chloro-6-fluorophenyl
H
H
H
H
H
CF3
OH


I-390
4-chloro-2-fluorophenyl
H
H
H
H
H
CF3
OH


I-391
4-chloro-2-nitrophenyl
H
H
H
H
H
CF3
OH


I-392
2,3,6-trifluorophenyl
H
H
H
H
H
CF3
OH


I-393
2,3,4,5,6-pentafluorophenyl
H
H
H
H
H
CF3
OH


I-394
pyridin-2-yl
H
H
H
H
H
CF3
OH


I-395
pyridin-3-yl
H
H
H
H
H
CF3
OH


I-396
2-fluoropyridin-3-yl
H
H
H
H
H
CF3
OH


I-397
2-chloropyridin-3-yl
H
H
H
H
H
CF3
OH


I-398
4-chloropyridin-3-yl
H
H
H
H
H
CF3
OH


I-399
2-chloropyridin-5-yl
H
H
H
H
H
CF3
OH


I-400
2-methylthiopyridin-3-yl
H
H
H
H
H
CF3
OH


I-401
2,6-dichloropyridin-3-yl
H
H
H
H
H
CF3
OH


I-402
2,6-dichloropyridin-4-yl
H
H
H
H
H
CF3
OH


I-403
pyrazin-2-yl
H
H
H
H
H
CF3
OH


I-404
furan-2-yl
H
H
H
H
H
CF3
OH


I-405
thiophen-2-yl
H
H
H
H
H
CF3
OH


I-406
thiophen-3-yl
H
H
H
H
H
CF3
OH


I-407
4-methoxyphenyl
H
H
H
H
H
CF3
OH


I-408
3,4,5-trimethoxyphenyl
H
H
H
H
H
CF3
OH


I-409
3-methoxyphenyl
H
H
H
H
H
CF3
OH


I-410
2-methoxyphenyl
H
H
H
H
H
CF3
OH


I-411
3,5-dimethoxyphenyl
H
H
H
H
H
CF3
OH


I-412
2,6-dimethoxyphenyl
H
H
H
H
H
CF3
OH


I-413
4-ethoxyphenyl
H
H
H
H
H
CF3
OH


I-414
2-(4-trifluoromethylphenyl)phenyl
H
H
H
H
H
CF3
OH


I-415
I-phenyl-5-trifluoromethylpyrazol-4-yl
H
H
H
H
H
CF3
OH


I-416
5-methylisoxazol-3-yl
H
H
H
H
H
CF3
OH


I-417
4-methyl-1,2,3-thiadiazoI-5-yl
H
H
H
H
H
CF3
OH


I-418
pyrrole-2-yl
H
H
H
H
H
CF3
OH


I-419
phenyl
H
H
H
H
H
CF3
Cl


I-420
2-methylphenyl
H
H
H
H
H
CF3
Cl


I-421
4-methylphenyl
H
H
H
H
H
CF3
Cl


I-422
2-fluorophenyl
H
H
H
H
H
CF3
Cl


I-423
3-fluorophenyl
H
H
H
H
H
CF3
Cl


I-424
4-fluorophenyl
H
H
H
H
H
CF3
Cl


I-425
2-chlorophenyl
H
H
H
H
H
CF3
Cl


I-426
4-chlorophenyl
H
H
H
H
H
CF3
Cl


I-427
2-bromophenyl
H
H
H
H
H
CF3
Cl


I-428
2-iodophenyl
H
H
H
H
H
CF3
Cl


I-429
3-cyanophenyl
H
H
H
H
H
CF3
Cl


I-430
4-cyanophenyl
H
H
H
H
H
CF3
Cl


I-431
2-nitrophenyl
H
H
H
H
H
CF3
Cl


I-432
3-nitrophenyl
H
H
H
H
H
CF3
Cl


I-433
4-nitrophenyl
H
H
H
H
H
CF3
Cl


I-434
2-trifluoromethylphenyl
H
H
H
H
H
CF3
Cl


I-435
4-trifluoromethylphenyl
H
H
H
H
H
CF3
Cl


I-436
4-trifluoromethoxyphenyl
H
H
H
H
H
CF3
Cl


I-437
2,3-difluorophenyl
H
H
H
H
H
CF3
Cl


I-438
2,4-difluorophenyl
H
H
H
H
H
CF3
Cl


I-439
2,5-difluorophenyl
H
H
H
H
H
CF3
Cl


I-440
2,6-difluorophenyl
H
H
H
H
H
CF3
Cl


I-441
2,4-dichlorophenyl
H
H
H
H
H
CF3
Cl


I-442
2,6-dichlorophenyl
H
H
H
H
H
CF3
Cl


I-443
3,4-dichlorophenyl
H
H
H
H
H
CF3
Cl


I-444
2-chloro-4-nitrophenyl
H
H
H
H
H
CF3
Cl


I-445
2-chloro-4-fluorophenyl
H
H
H
H
H
CF3
Cl


I-446
2-chloro-6-fluorophenyl
H
H
H
H
H
CF3
Cl


I-447
4-chloro-2-fluorophenyl
H
H
H
H
H
CF3
Cl


I-448
4-chloro-2-nitrophenyl
H
H
H
H
H
CF3
Cl


I-449
2,3,6-trifluorophenyl
H
H
H
H
H
CF3
Cl


I-450
pyridin-2-yl
H
H
H
H
H
CF3
Cl


I-451
pyridin-3-yl
H
H
H
H
H
CF3
Cl


I-452
2-fluoropyridin-3-yl
H
H
H
H
H
CF3
Cl


I-453
2-chloropyridin-3-yl
H
H
H
H
H
CF3
Cl


I-454
2-chloropyridin-5-yl
H
H
H
H
H
CF3
Cl


I-455
2-methylthiopyridin-3-yl
H
H
H
H
H
CF3
Cl


I-456
pyrazin-2-yl
H
H
H
H
H
CF3
Cl


I-457
furan-2-yl
H
H
H
H
H
CF3
Cl


I-458
thiophen-2-yl
H
H
H
H
H
CF3
Cl


I-459
phenyl
F
H
H
H
H
CF3
OH


I-460
2-methylphenyl
F
H
H
H
H
CF3
OH


I-461
4-methylphenyl
F
H
H
H
H
CF3
OH


I-462
2-fluorophenyl
F
H
H
H
H
CF3
OH


I-463
3-fluorophenyl
F
H
H
H
H
CF3
OH


I-464
4-fluorophenyl
F
H
H
H
H
CF3
OH


I-465
2-chlorophenyl
F
H
H
H
H
CF3
OH


I-466
4-chlorophenyl
F
H
H
H
H
CF3
OH


I-467
2-bromophenyl
F
H
H
H
H
CF3
OH


I-468
2-iodophenyl
F
H
H
H
H
CF3
OH


I-469
3-cyanophenyl
F
H
H
H
H
CF3
OH


I-470
4-cyanophenyl
F
H
H
H
H
CF3
OH


I-471
2-nitrophenyl
F
H
H
H
H
CF3
OH


I-472
3-nitrophenyl
F
H
H
H
H
CF3
OH


I-473
4-nitrophenyl
F
H
H
H
H
CF3
OH


I-474
2-trifluoromethylphenyl
F
H
H
H
H
CF3
OH


I-475
4-trifluoromethylphenyl
F
H
H
H
H
CF3
OH


I-476
4-trifluoromethoxyphenyl
F
H
H
H
H
CF3
OH


I-477
2,3-difluorophenyl
F
H
H
H
H
CF3
OH


I-478
2,4-difluorophenyl
F
H
H
H
H
CF3
OH


I-479
2,5-difluorophenyl
F
H
H
H
H
CF3
OH


I-480
2,6-difluorophenyl
F
H
H
H
H
CF3
OH


I-481
2,4-dichlorophenyl
F
H
H
H
H
CF3
OH


I-482
2,6-dichlorophenyl
F
H
H
H
H
CF3
OH


I-483
3,4-dichlorophenyl
F
H
H
H
H
CF3
OH


I-484
2-chloro-4-nitrophenyl
F
H
H
H
H
CF3
OH


I-485
2-chloro-4-fluorophenyl
F
H
H
H
H
CF3
OH


I-486
2-chloro-6-fluorophenyl
F
H
H
H
H
CF3
OH


I-487
4-chloro-2-fluorophenyl
F
H
H
H
H
CF3
OH


I-488
4-chloro-2-nitrophenyl
F
H
H
H
H
CF3
OH


I-489
2,3,6-trifluorophenyl
F
H
H
H
H
CF3
OH


I-490
pyridin-2-yl
F
H
H
H
H
CF3
OH


I-491
pyridin-3-yl
F
H
H
H
H
CF3
OH


I-492
2-fluoropyridin-3-yl
F
H
H
H
H
CF3
OH


I-493
2-chloropyridin-3-yl
F
H
H
H
H
CF3
OH


I-494
2-chloropyridin-5-yl
F
H
H
H
H
CF3
OH


I-495
2-methylthiopyridin-3-yl
F
H
H
H
H
CF3
OH


I-496
pyrazin-2-yl
F
H
H
H
H
CF3
OH


I-497
furan-2-yl
F
H
H
H
H
CF3
OH


I-498
thiophen-2-yl
F
H
H
H
H
CF3
OH


I-499
phenyl
F
H
H
H
H
CF3
Cl


I-500
2-methylphenyl
F
H
H
H
H
CF3
Cl


I-501
4-methylphenyl
F
H
H
H
H
CF3
Cl


I-502
2-fluorophenyl
F
H
H
H
H
CF3
Cl


I-503
3-fluorophenyl
F
H
H
H
H
CF3
Cl


I-504
4-fluorophenyl
F
H
H
H
H
CF3
Cl


I-505
2-chlorophenyl
F
H
H
H
H
CF3
Cl


I-506
4-chlorophenyl
F
H
H
H
H
CF3
Cl


I-507
2-bromophenyl
F
H
H
H
H
CF3
Cl


I-508
2-iodophenyl
F
H
II
H
H
CF3
Cl


I-509
3-cyanophenyl
F
H
H
H
H
CF3
Cl


I-510
4-cyanophenyl
F
H
H
H
H
CF3
Cl


I-511
2-nitrophenyl
F
H
H
H
H
CF3
Cl


I-512
3-nitrophenyl
F
H
H
H
H
CF3
Cl


I-513
4-nitrophenyl
F
H
H
H
H
CF3
Cl


I-514
2-trifluoromethylphenyl
F
H
H
H
H
CF3
Cl


I-515
4-trifluoromethylphenyl
F
H
H
H
H
CF3
Cl


I-516
4-trifluoromethoxyphenyl
F
H
H
H
H
CF3
Cl


I-517
2,3-difluorophenyl
F
H
H
H
H
CF3
Cl


I-518
2,4-difluorophenyl
F
H
H
H
H
CF3
Cl


I-519
2,5-difluorophenyl
F
H
H
H
H
CF3
Cl


I-520
2,6-difluorophenyl
F
H
H
H
H
CF3
Cl


I-521
2,4-dichlorophenyl
F
H
H
H
H
CF3
Cl


I-522
2,6-dichlorophenyl
F
H
H
H
H
CF3
Cl


I-523
3,4-dichlorophenyl
F
H
H
H
H
CF3
Cl


I-524
2-chloro-4-nitrophenyl
F
H
H
H
H
CF3
Cl


I-525
2-chloro-4-fluorophenyl
F
H
H
H
H
CF3
Cl


I-526
2-chloro-6-fluorophenyl
F
H
H
H
H
CF3
Cl


I-527
4-chloro-2-fluorophenyl
F
H
H
H
H
CF3
Cl


I-528
4-chloro-2-nitrophenyl
F
H
H
H
H
CF3
Cl


I-529
2,3,6-trifluorophenyl
F
H
H
H
H
CF3
Cl


I-530
pyridin-2-yl
F
H
H
H
H
CF3
Cl


I-531
pyridin-3-yl
F
H
H
H
H
CF3
Cl


I-532
2-fluoropyridin-3-yl
F
H
H
H
H
CF3
Cl


I-533
2-chloropyridin-3-yl
F
H
H
H
H
CF3
Cl


I-534
2-chloropyridin-5-yl
F
H
H
H
H
CF3
Cl


I-535
2-methylthiopyridin-3-yl
F
H
H
H
H
CF3
Cl


I-536
pyrazin-2-yl
F
H
H
H
H
CF3
Cl


I-537
furan-2-yl
F
H
H
H
H
CF3
Cl


I-538
thiophen-2-yl
F
H
H
H
H
CF3
Cl


I-539
phenyl
H
Me
H
H
H
CF3
OH


I-540
2-methylphenyl
H
Me
H
H
H
CF3
OH


I-541
4-methylphenyl
H
Me
H
H
H
CF3
OH


I-542
2-fluorophenyl
H
He
H
H
H
CF3
OH


I-543
3-fluorophenyl
H
Me
H
H
H
CF3
OH


I-544
4-fluorophenyl
H
Me
H
H
H
CF3
OH


I-545
2-chlorophenyl
H
Me
H
H
H
CF3
OH


I-546
4-chlorophenyl
H
Me
H
H
H
CF3
OH


I-547
2-bromophenyl
H
Me
H
H
H
CF3
OH


I-548
2-iodophenyl
H
Me
H
H
H
CF3
OH


I-549
3-cyanophenyl
H
Me
H
H
H
CF3
OH


I-550
4-cyanophenyl
H
Me
H
H
H
CF3
OH


I-551
2-nitrophenyl
H
Me
H
H
H
CF3
OH


I-552
3-nitrophenyl
H
Me
H
H
H
CF3
OH


I-553
4-nitrophenyl
H
Me
H
H
H
CF3
OH


I-554
2-trifluoromethylphenyl
H
Me
H
H
H
CF3
OH


I-555
4-trifluoromethylphenyl
H
Me
H
H
H
CF3
OH


I-556
4-trifluoromethoxyphenyl
H
He
H
H
H
CF3
OH


I-557
2,3-difluorophenyl
H
Me
H
H
H
CF3
OH


I-558
2,4-difluorophenyl
H
Me
H
H
H
CF3
OH


I-559
2,5-difluorophenyl
H
Me
H
H
H
CF3
OH


I-560
2,6-difluorophenyl
H
Me
H
H
H
CF3
OH


I-561
2,4-dichlorophenyl
H
Me
H
H
H
CF3
OH


I-562
2,6-dichlorophenyl
H
Me
H
H
H
CF3
OH


I-563
3,4-dichlorophenyl
H
Me
H
H
H
CF3
OH


I-564
2-chloro-4-nitrophenyl
H
Me
H
H
H
CF3
OH


I-565
2-chloro-4-fluorophenyl
H
Me
H
H
H
CF3
OH


I-566
2-chloro-6-fluorophenyl
H
me
H
H
H
CF3
OH


I-567
4-chloro-2-fluorophenyl
H
Me
H
H
H
CF3
OH


I-568
4-chloro-2-nitrophenyl
H
Me
H
H
H
CF3
OH


I-569
2,3,6-trifluorophenyl
H
Me
H
H
H
CF3
OH


I-570
pyridin-2-yl
H
Me
H
H
H
CF3
OH


I-571
pyridin-3-yl
H
Me
H
H
H
CF3
OH


I-572
2-fluoropyridin-3-yl
H
Me
H
H
H
CF3
OH


I-573
2-chloropyridin-3-yl
H
Me
H
H
H
CF3
OH


I-574
2-chloropyridin-5-yl
H
Me
H
H
H
CF3
OH


I-575
2-methylthiopyridin-3-yl
H
Me
H
H
H
CF3
OH


I-576
pyrazin-2-yl
H
Me
H
H
H
CF3
OH


I-577
furan-2-yl
H
Me
H
H
H
CF3
OH


I-578
thiophen-2-yl
H
Me
H
H
H
CF3
OH


I-579
phenyl
F
Me
H
H
H
CF3
Cl


I-580
2-methylphenyl
F
Me
H
H
H
CF3
Cl


I-581
4-methylphenyl
F
Me
H
H
H
CF3
Cl


I-582
2-fluorophenyl
F
Me
H
H
H
CF3
Cl


I-583
3-fluorophenyl
F
Me
H
H
H
CF3
Cl


I-584
4-fluorophenyl
F
Me
H
H
H
CF3
Cl


I-585
2-chlorophenyl
F
Me
H
H
H
CF3
Cl


I-586
4-chlorophenyl
F
Me
H
H
H
CF3
Cl


I-587
2-bromophenyl
F
Me
H
H
H
CF3
Cl


I-588
2-iodophenyl
F
Me
H
H
H
CF3
Cl


I-589
3-cyanophenyl
F
Me
H
H
H
CF3
Cl


I-590
4-cyanophenyl
F
He
H
H
H
CF3
Cl


I-591
2-nitrophenyl
F
Me
H
H
H
CF3
Cl


I-592
3-nitrophenyl
F
Me
H
H
H
CF3
Cl


I-593
4-nitrophenyl
F
Me
H
H
H
CF3
Cl


I-594
2-trifluoromethylphenyl
F
Me
H
H
H
CF3
Cl


I-595
4-trifluoromethylphenyl
F
Me
H
H
H
CF3
Cl


I-596
4-trifluoromethoxyphenyl
F
Me
H
H
H
CF3
Cl


I-597
2,3-difluorophenyl
F
Me
H
H
H
CF3
Cl


I-598
2,4-difluorophenyl
F
Me
H
H
H
CF3
Cl


I-599
2,5-difluorophenyl
F
Me
H
H
H
CF3
Cl


I-600
2,6-difluorophenyl
F
Me
H
H
H
CF3
Cl


I-601
2,4-dichlorophenyl
F
Me
H
H
H
CF3
Cl


I-602
2,6-dichlorophenyl
F
Me
H
H
H
CF3
Cl


I-603
3,4-dichlorophenyl
F
Me
H
H
H
CF3
Cl


I-604
2-chloro-4-nitrophenyl
F
Me
H
H
H
CF3
Cl


I-605
2-chloro-4-fluorophenyl
F
Me
H
H
H
CF3
Cl


I-606
2-chloro-6-fluorophenyl
F
Me
H
H
H
CF3
Cl


I-607
4-chloro-2-fluorophenyl
F
Me
H
H
H
CF3
Cl


I-608
4-chloro-2-nitrophenyl
F
Me
H
H
H
CF3
Cl


I-609
2,3,6-trifluorophenyl
F
Me
H
H
H
CF3
Cl


I-610
pyridin-2-yl
F
Me
H
H
H
CF3
Cl


I-611
pyridin-3-yl
F
Me
H
H
H
CF3
Cl


I-612
2-fluoropyridin-3-yl
F
Me
H
H
H
CF3
Cl


I-613
2-chloropyridin-3-yl
F
Me
H
H
H
CF3
Cl


I-614
2-chloropyridin-5-yl
F
Me
H
H
H
CF3
Cl


I-615
2-methylthiopyridin-3-yl
F
Me
H
H
H
CF3
Cl


I-616
pyrazin-2-yl
F
Me
H
H
H
CF3
Cl


I-617
furan-2-yl
F
He
H
H
H
CF3
Cl


I-618
thiophen-2-yl
F
Me
H
H
H
CF3
Cl


I-619
phenyl
H
Me
Me
H
H
CF3
OH


I-620
2-methylphenyl
H
Me
Me
H
H
CF3
OH


I-621
4-methylphenyl
H
Me
Me
H
H
CF3
OH


I-622
2-fluorophenyl
H
Me
Me
H
H
CF3
OH


I-623
3-fluorophenyl
H
Me
Me
H
H
CF3
OH


I-624
4-fluorophenyl
H
Me
Me
H
H
CF3
OH


I-625
2-chlorophenyl
H
Me
Me
H
H
CF3
OH


I-626
4-chlorophenyl
H
Me
Me
H
H
CF3
OH


I-627
2-bromophenyl
H
Me
Me
H
H
OF,
OH


I-628
2-iodophenyl
H
Me
Me
H
H
CF3
OH


I-629
3-cyanophenyl
H
Me
Me
H
H
CF3
OH


I-630
4-cyanophenyl
H
Me
Me
H
H
CF3
OH


I-631
2-nitrophenyl
H
Me
Me
H
H
CF3
OH


I-632
3-nitrophenyl
H
Me
Me
H
H
CF3
OH


I-633
4-nitrophenyl
H
Me
Me
H
H
CF3
OH


I-634
2-trifluoromethylphenyl
H
Me
Me
H
H
CF3
OH


I-635
4-trifluoromethylphenyl
H
Me
Me
H
H
CF3
OH


I-636
4-trifluoromethoxyphenyl
H
Me
Me
H
H
CF3
OH


I-637
2,3-difluorophenyl
H
Me
Me
H
H
CF3
OH


I-638
2,4-difluorophenyl
H
Me
Me
H
H
CF3
OH


I-639
2,5-difluorophenyl
H
Me
Me
H
H
CF3
OH


I-640
2,6-difluorophenyl
H
Me
Me
H
H
CF3
OH


I-641
2,4-dichlorophenyl
H
me
Me
H
H
CF3
OH


I-642
2,6-dichlorophenyl
H
Me
Me
H
H
CF3
OH


I-643
3,4-dichlorophenyl
H
Me
Me
H
H
CF3
OH


I-644
2-chloro-4-nitrophenyl
H
Me
Me
H
H
CF3
OH


I-645
2-chloro-4-fluorophenyl
H
Me
Me
H
H
CF3
OH


I-646
2-chloro-6-fluorophenyl
H
Me
Me
H
H
CF3
OH


I-647
4-chloro-2-fluorophenyl
H
Me
Me
H
H
CF3
OH


I-648
4-chloro-2-nitrophenyl
H
Me
Me
H
H
CF3
OH


I-649
2,3,6-trifluorophenyl
H
Me
Me
H
H
CF3
OH


I-650
pyridin-2-yl
H
Me
Me
H
H
CF3
OH


I-651
pyridin-3-yl
H
Me
Me
H
H
CF3
OH


I-652
2-fluoropyridin-3-yl
H
Me
Me
H
H
CF3
OH


I-653
2-chloropyridin-3-yl
H
Me
Me
H
H
CF3
OH


I-654
2-chloropyridin-5-yl
H
Me
Me
H
H
CF3
OH


I-655
2-methylthiopyridin-3-yl
H
Me
Me
H
H
CF3
OH


I-656
pyrazin-2-yl
H
Me
Me
H
H
CF3
OH


I-657
furan-2-yl
H
Me
Me
H
H
CF3
OH


I-658
thiophen-2-yl
H
Me
Me
H
H
CF3
OH


I-659
phenyl
F
Me
Me
H
H
CF3
Cl


I-660
2-methylphenyl
F
Me
Me
H
H
CF3
Cl


I-661
4-methylphenyl
F
Me
Me
H
H
CF3
Cl


I-662
2-fluorophenyl
F
Me
Me
H
H
CF3
Cl


I-663
3-fluorophenyl
F
Me
Me
H
H
CF3
Cl


I-664
4-fluorophenyl
F
Me
Me
H
H
CF3
Cl


I-665
2-chlorophenyl
F
Me
Me
H
H
CF3
Cl


I-666
4-chlorophenyl
F
Me
Me
H
H
CF3
Cl


I-667
2-bromophenyl
F
Me
Me
H
H
CF3
Cl


I-668
2-iodophenyl
F
Me
Me
H
H
CF3
Cl


I-669
3-cyanophenyl
F
Me
Me
H
H
CF3
Cl


I-670
4-cyanophenyl
F
Me
Me
H
H
CF3
Cl


I-671
2-nitrophenyl
F
Me
Me
H
H
CF3
Cl


I-672
3-nitrophenyl
F
Me
Me
H
H
CF3
Cl


I-673
4-nitrophenyl
F
Me
Me
H
H
CF3
Cl


I-674
2-trifluoromethylphenyl
F
Me
Me
H
H
CF3
Cl


I-675
4-trifluoromethylphenyl
F
Me
Me
H
H
CF3
Cl


I-676
4-trifluoromethoxyphenyl
F
Me
Me
H
H
CF3
Cl


I-677
2,3-difluorophenyl
F
Me
Me
H
H
CF3
Cl


I-678
2,4-difluorophenyl
F
Me
Me
H
H
CF3
Cl


I-679
2,5-difluorophenyl
F
Me
Me
H
H
CF3
Cl


I-680
2,6-difluorophenyl
F
Me
Me
H
H
CF3
Cl


I-681
2,4-dichlorophenyl
F
Me
Me
H
H
CF3
Cl


I-682
2,6-dichlorophenyl
F
Me
Me
H
H
CF3
Cl


I-683
3,4-dichlorophenyl
F
Me
Me
H
H
CF3
Cl


I-684
2-chloro-4-nitrophenyl
F
Me
Me
H
H
CF3
Cl


I-685
2-chloro-4-fluorophenyl
F
Me
Me
H
H
CF3
Cl


I-686
2-chloro-6-fluorophenyl
F
Me
Me
H
H
CF3
Cl


I-687
4-chloro-2-f1uorophenyl
F
Me
Me
H
H
CF3
Cl


I-668
4-chloro-2-nitrophenyl
F
Me
Me
H
H
CF3
Cl


I-689
2,3,6-trifluorophenyl
F
Me
Me
H
H
CF3
Cl


I-690
pyridin-2-yl
F
Me
Me
H
H
CF3
Cl


I-691
pyridin-3-yl
F
Me
Me
H
H
CF3
Cl


I-692
2-fluoropyridin-3-yl
F
Me
Me
H
H
CF3
Cl


I-693
2-chloropyridin-3-yl
F
Me
Me
H
H
CF3
Cl


I-694
2-chloropyridin-5-yl
F
Me
Me
H
H
CF3
Cl


I-695
2-methylthiopyridin-3-yl
F
Me
Me
H
H
CF3
Cl


I-696
pyrazin-2-yl
F
Me
Me
H
H
CF3
Cl


I-697
furan-2-yl
F
'Me
Me
H
H
CF3
Cl


I-698
thiophen-2-yl
F
Me
Me
H
H
CF3
Cl


I-699
2-fluorophenyl
H
H
H
MeSO2
Br
CF3
OH


I-700
2-fluorophenyl
H
H
H
MeSO2
Br
CF3
Cl


I-701
2-fluorophenyl
F
H
H
MeSO2
Br
CF3
OH


I-702
2-fluorophenyl
F
H
H
MeSO2
Br
CF3
Cl


I-703
2-fluorophenyl
H
Me
H
MeSO2
Br
CF3
OH


I-704
2-fluorophenyl
H
Me
H
MeSO2
Br
CF3
Cl


I-705
2-fluorophenyl
F
Me
H
MeSO2
Br
CF3
OH


I-706
2-fluorophenyl
F
Me
H
MeSO2
Br
CF3
Cl


I-707
2-fluorophenyl
H
Me
Me
MeSO2
Br
CF3
OH


I-708
2-fluorophenyl
H
He
Me
MeSO2
Br
CF3
Cl


I-709
2-fluorophenyl
F
Me
Me
MeSO2
Br
CF3
OH


I-710
2-fluorophenyl
F
Me
Me
MeSO2
Br
CF3
Cl


I-711
2-fluorophenyl
H
H
H
n-Pr
I
CF3
OH


I-712
2-fluorophenyl
H
H
H
n-Pr
I
CF3
Cl


I-713
2-fluorophenyl
F
H
H
n-Pr
I
CF3
OH


I-714
2-fluorophenyl
F
H
H
n-Pr
I
CF3
Cl


I-715
2-fluorophenyl
H
Me
H
n-Pr
I
CF3
OH


I-716
2-fluorophenyl
H
Me
H
n-Pr
I
CF3
Cl


I-717
2-fluorophenyl
F
Me
H
n-Pr
I
CF3
OH


I-718
2-fluorophenyl
F
Me
H
n-Pr
I
CF3
Cl


I-719
2-fluorophenyl
H
Me
Me
n-Pr
I
CF3
OH


I-720
2-fluorophenyl
H
Me
Me
n-Pr
I
CF3
Cl


I-721
2-fluorophenyl
F
Me
Me
n-Pr
I
CF3
OH


I-722
2-fluorophenyl
F
Me
Me
n-Pr
I
CF3
Cl


I-723
2-fluorophenyl
H
H
H
H
H
C2F5
OH


I-724
2-fluorophenyl
H
H
H
H
H
C2F5
Cl


I-725
2-fluorophenyl
F
H
H
H
H
C2F5
OH


I-726
2-fluorophenyl
F
H
H
H
H
C2F5
Cl


I-727
2-fluorophenyl
H
Me
H
H
H
C2F5
OH


I-728
2-fluorophenyl
H
Me
H
H
H
C2F5
Cl


I-729
2-fluorophenyl
F
Me
H
H
H
C2F5
OH


I-730
2-fluorophenyl
F
Me
H
H
H
C2F5
Cl


I-731
2-fluorophenyl
H
Me
Me
H
H
C2F5
OH


I-732
2-fluorophenyl
H
Me
Me
H
H
C2F5
Cl


I-733
2-fluorophenyl
F
Me
Me
H
H
C2F5
OH


I-734
2-fluorophenyl
F
Me
Me
H
H
C2F5
Cl


I-35
2-fluorophenyl
H
H
H
H
H
CF3
Br


I-736
2-fluorophenyl
H
H
H
H
H
CF3
Br


I-737
2-fluorophenyl
F
H
H
H
H
CF3
Br


I-738
2-fluorophenyl
F
H
H
H
H
CF3
Br


I-739
2-fluorophenyl
H
Me
H
H
H
CF3
Br


I-740
2-fluorophenyl
H
Me
H
H
H
CF3
Br


I-741
2-fluorophenyl
F
Me
H
H
H
CF3
Br


I-742
2-fluorophenyl
F
He
H
H
H
CF3
Br


I-743
2-fluorophenyl
H
Me
Me
H
H
CF3
Br


I-744
2-fluorophenyl
H
Me
Me
H
H
CF3
Br


I-745
2-fluorophenyl
F
Me
Me
H
H
CF3
Br


I-746
2-fluorophenyl
F
Me
Me
H
H
CF3
Br









Hereinbelow, Table 11 and Table 12 represent the properties of the compounds represented by Formulae (1), (6), (8), (11) and (13). The 1H-NMR chemical shift values represented therein are based on tetramethylsilane as the internal standard substance, if not described otherwise.










TABLE 11







Comp. No.

1H-NMR (DMSO-d6, ppm)






1
(CDCl3) δ 2.36 (6H, s), 7.36 (2H, s), 7.51-7.65 (5H, m), 7.73 (1H, d, J = 7.8 Hz), 7.86 (1H, d, J = 7.8 Hz),



7.89 (2H, d, J = 7.8 Hz), 8.01 (1H, s), 8.33 (1H, s).


2
δ 7.52-7.63 (4H, m), 7.77 (1H, d, J = 7.8 Hz), 7.98-8.09 (5H, m), 8.39 (1H, s), 10.48 (1H, s), 10.59 (1H,



s).


3
δ 7.32-7.39 (2H, m), 7.54-7.63 (2H, m), 7.67-7.72 (1H, m), 7.77 (1H, d, J = 7.8 Hz), 7.98 (1H, d, J = 7.8 Hz),



8.03 (2H, s), 8.34 (1H, s), 10.61 (1H, s), 10.65 (1H, s).


4
δ 7.53-7.63 (4H, m), 7.79 (1H, d, J = 8.3 Hz), 7.99-8.02 (2H, m), 8.08 (1H, dd, J = 2.0, 8.3 Hz),



8.17 (2H, s), 8.39 (1H, d, J = 2.0 Hz), 10.50 (1H, s), 10.63 (1H, s).


5
δ 7.33-7.40 (2H, m), 7.54-7.63 (2H, m), 7.68-7.72 (1H, m), 7.79 (1H, d, J = 7.8 Hz), 7.99 (1H, d, J = 7.8 Hz),



8.17 (2H, s), 8.35 (1H, s), 10.65 (1H, s), 10.67 (1H, s).


6
δ 7.52-7.62 (4H, m), 7.75 (1H, d, J = 7.8 Hz), 7.91 (2H, s), 7.97 (2H, d, J = 7.8 Hz),



8.04 (1H, d, J = 7.8 Hz), 8.36 (1H, s), 10.50 (1H, s), 10.61 (1H, s).


7
δ 7.53-7.64 (4H, m), 7.78 (1H, d, J = 7.8 Hz), 7.99-8.01 (2H, m), 8.06 (2H, s), 8.09 (1H, dd, J = 2.0,



7.8 Hz), 8.39 (1H, s), 10.51 (1H, s), 10.63 (1H, s).


8
δ 7.33-7.40 (2H, m), 7.55-7.63 (2H, m), 7.68-7.72 (1H, m), 7.78 (1H, d, J = 7.8 Hz), 7.99 (1H, d, J = 7.8 Hz),



8.05 (2H, s), 8.34 (1H, s), 10.65 (1H, s), 10.69 (1H, s).


9
δ 2.29 (6H, s), 7.47 (2H, s), 7.51-7.62 (4H, m), 7.75 (1H, d, J = 7.8 Hz), 7.97-8.00 (2H, m),



8.03-8.06 (1H, m), 8.36 (1H, s), 10.00 (1H, s), 10.45 (1H, s).


10
δ 2.37 (6H, s), 7.34 (2H, s), 7.46-7.57 (4H, m), 7.75 (1H, d, J = 7.8 Hz), 7.98-8.01 (2H, m), 8.12 (1H,



d, J = 7.3 Hz), 8.34 (1H, s), 8.87 (1H, s), 9.66 (1H, s).


11
(CDCl3) δ 2.35 (6H, s), 2.52 (3H, s), 7.26-7.31 (2H, m), 7.36 (2H, s), 7.37-7.42 (1H, m),



7.49-7.54 (2H, m), 7.68-7.73 (3H, m), 7.79 (1H, d, J = 7.3 Hz), 8.30 (1H, s).


12
δ 2.30 (6H, s), 2.41 (3H, s), 7.42-7.48 (4H, m), 7.54 (1H, d, J = 7.94 Hz), 7.74-7.82 (3H, m), 8.07 (1H,



d, J = 7.94 Hz), 8.35 (1H, s), 9.99 (1H, s), 10.43 (1H, s).


13
δ 2.30 (6H, s), 2.40 (3H, s), 7.35 (2H, d, J = 8.3 Hz), 7.45 (2H, s), 7.53 (1H, t, J = 7.8 Hz), 7.74 (1H, d,



J = 7.81 Hz), 7.92 (2H, d, J = 8.3 Hz), 8.07 (1H, d, J = 7.8 Hz), 8.36 (1H, s), 9.98 (1H, s), 10.39 (1H, s).


14
δ 1.18 (3H, t, J = 7.6 Hz), 2.30 (6H, s), 2.76 (2H, q, J = 7.6 Hz), 7.30-7.37 (2H, m), 7.42-7.46 (4H, m),



7.52 (1H, t, J = 8.0 Hz), 7.81 (1H, d, J = 8.0 Hz), 7.96 (1H, d, J = 8.0 Hz), 8.35 (1H, s), 9.98 (1H, s),



10.56 (1H, s).


16
δ 1.22 (3H, t, J = 7.6 Hz), 2.31 (6H, s), 2.69 (2H, q, J = 7.6 Hz), 7.39 (2H, d, J = 8.3 Hz), 7.45 (2H, t, J = 7.9 Hz),



7.53 (2H, d, J = 8.3 Hz), 7.74 (1H, d, J = 7.9 Hz), 7.94 (1H, d, J = 8.3 Hz), 8.07 (1H, d, J = 7.9 Hz),



8.36 (1H, s), 9.99 (1H, s), 10.40 (1H, s).


17
δ 2.30 (6H, s), 7.33-7.76 (8H, m), 7.97 (1H, d, J = 8.30 Hz), 8.30 (1H, s), 10.01 (1H, s), 10.65 (1H, s).


18
δ 2.30 (6H, s), 7.45-7.64 (5H, m), 7.76-8.05 (3H, m), 8.06 (1H, d, J = 8.3 Hz), 8.35 (1H, s), 10.00 (1H,



s), 10.54 (1H, s).


19
δ 2.30 (6H, s), 7.37-7.45 (4H, m), 7.54 (1H, t, J = 7.8 Hz), 7.76 (1H, d, J = 7.8 Hz), 8.05-8.11 (3H, m),



8.34 (1H, s), 10.00 (1H, s), 10.49 (1H, s).


20
(CDCl3) δ 2.35 (6H, s), 7.36 (2H, s), 7.37-7.54 (4H, m), 7.69-7.83 (4H, m),



8.13 (1H, s), 8.33 (1H, s).


22
δ 2.30 (6H, s), 7.45 (2H, s), 7.56 (1H, dd, J = 7.8, 6.8 Hz), 7.63 (1H, d, J = 8.8 Hz), 7.72 (1H, d, J = 8.8 Hz),



7.77 (1H, d, J = 6.8 Hz), 7.94 (1H, d, J = 8.3 Hz), 8.03 (1H, d, J = 8.8 Hz), 8.17 (1H, d, J = 7.8 Hz), 8.34 (1H,



s), 9.99 (1H, s), 10.54 (1H, s).


23
(CDCl3) δ 2.36 (6H, s), 7.34-7.38 (3H, m), 7.42-7.46 (1H, m), 7.53 (1H, t, J = 7.8 Hz), 7.62 (1H, s),



7.65-7.68 (2H, m), 7.73-7.75 (1H, m), 7.82-7.84 (1H, m), 7.89 (1H, s), 8.32 (1H, s).


26
(CDCl3) δ 2.36 (6H, s), 7.19 (1H, dt, J = 2.0, 7.8 Hz), 7.36 (2H, s), 7.46 (1H, t, J = 7.8 Hz),



7.52-7.57 (3H, m), 7.66 (1H, s), 7.74 (1H, d, J = 7.8 Hz), 7.85 (1H, d, J = 7.8 Hz), 7.94 (1H, d, J = 7.8 Hz),



8.31 (1H, s)


28
δ 2.36 (6H, s), 7.33 (2H, s), 7.48 (1H, t, J = 7.8 Hz), 7.75-7.84 (5H, m), 8.14 (1H, d, J = 7.8 Hz), 8.31 (1H,



s), 9.20 (1H, s), 10.04 (1H, s).


29
δ 2.30 (6H, s), 7.45 (2H, s), 7.57 (1H, d, J = 7.8 Hz), 7.75-7.80 (2H, m),



8.06-8.11 (2H, m), 8.29 (1H, d, J = 7.8 Hz), 8.34 (1H, s), 8.46 (1H, s), 10.02 (1H, s), 10.65 (1H, s).


30
δ 2.30 (6H, s), 7.45 (2H, s), 7.56 (1H, t, J = 7.8 Hz), 7.79 (1H, d, J = 7.8 Hz),



8.04-8.06 (3H, m), 8.16 (2H, d, J = 8.3 Hz), 8.36 (1H, s), 10.02 (1H, s), 10.72 (1H, s).


31
δ 2.30 (6H, s), 7.45 (2H, s), 7.56 (1H, d, J = 7.8 Hz), 7.76-7.81 (3H, m),



7.88-7.94 (2H, m), 8.17 (1H, d, J = 7.8 Hz), 8.24 (1H, s), 10.02 (1H, s), 10.90 (1H, s).


32
δ 2.32 (6H, s), 7.46 (2H, s), 7.58 (1H, t, J = 7.8 Hz), 7.80-7.89 (2H, m), 8.11 (1H, d,



J = 7.8 Hz), 8.36 (1H, s), 8.44-8.48 (2H, m), 8.86 (1H, s), 10.04 (1H, s), 10.83 (1H, s).


33
δ 2.31 (6H, s), 7.45 (2H, s), 7.57 (1H, t, J = 8.1 Hz), 7.80 (1H, d, J = 8.1 Hz), 8.08 (1H, d, J = 8.1 Hz),



8.24 (1H, s), 8.36-8.41 (4H, m), 10.01 (1H, s), 10.79 (1H, s).


34
δ 2.30 (6H, s), 6.39 (2H, s), 6.58-6.62 (1H, m), 6.76 (1H, dd, J = 1.0, 8.3 Hz),



7.19-7.24 (1H, m), 7.45 (2H, s), 7.51 (1H, t, J = 7.8 Hz), 7.66-7.73 (2H, m),



7.94-7.97 (1H, m), 8.30 (1H, d, J = 2.0 Hz), 9.96 (1H, s), 10.20 (1H, s).


35
δ 2.30 (6H, s), 6.53-6.86 (1H, m), 7.20-7.21 (4H, m), 7.45 (2H, s), 7.52 (1H, t, J = 7.8 Hz), 7.73 (1H, d,



J = 7.8 Hz), 8.02 (1H, d, J = 7.8 Hz), 8.35 (1H, s), 9.96 (1H, s), 10.32 (1H, s).


37
(CDCl3) δ 2.34 (6H, s), 7.35 (2H, s), 7.51 (1H, t, J = 7.8 Hz), 7.62-7.80 (8H, m), 8.25 (1H, s).


39
δ 2.31 (6H, s), 7.45 (2H, s), 7.57 (1H, t, J = 7.8 Hz), 7.79 (1H, d, J = 7.8 Hz), 7.94 (2H, d, J = 8.3 Hz),



8.07 (1H, d, J = 7.8 Hz), 8.20 (2H, d, J = 8.3 Hz), 8.36 (1H, s), 10.01 (1H, s), 10.70 (1H, s).


40
δ 2.30 (6H, s), 6.96-7.01 (2H, m), 7.43-7.48 (3H, m), 7.56 (1H, t, J = 8.3 Hz),



7.78 (1H, d, J = 8.3 Hz), 7.97-8.00 (2H, m), 8.29 (1H, s), 10.01 (1H, s), 10.61 (1H, s).


41
δ 2.30 (6H, s), 3.90 (3H, s), 7.05-7.10 (1H, m), 7.19 (1H, d, J = 8.3 Hz), 7.45 (2H, s),



7.49-7.54 (2H, m), 7.63 (1H, dd, J = 2.0, 7.8 Hz), 7.72 (1H, d, J = 7.8 Hz), 7.96 (1H, d,



J = 7.8 Hz), 8.33 (1H, s), 9.98 (1H, s), 10.33 (1H, s).


45
δ 1.33 (9H, s), 2.31 (6H, s), 7.45 (2H, s), 7.53 (1H, t, J = 7.8 Hz), 7.54 (2H, d, J = 8.3 Hz), 7.74 (1H, d, J = 7.8 Hz),



7.94 (2H, d, J = 8.3 Hz), 8.06 (1H, d, J = 7.8 Hz), 8.36 (1H, s), 9.99 (1H, s), 10.40 (1H, s).


46
δ 2.30 (6H, s), 2.98 (6H, s), 6.93-6.95 (1H, m), 7.25-7.35 (3H, m), 7.45 (2H, s),



7.53 (1H, t, J = 7.8 Hz), 7.74 (1H, d, J = 7.8 Hz), 8.06 (1H, d, J = 7.8 Hz), 8.35 (1H, s),



9.99 (1H, s), 10.35 (1H, s).


47
δ 2.30 (6H, s), 3.01 (6H, s), 6.77 (2H, d, J = 9.3 Hz), 7.45 (2H, s), 7.50 (1H, t, J = 7.8 Hz), 7.69 (1H, d, J = 7.8 Hz),



7.91 (2H, d, J = 9.3 Hz), 8.06 (1H, d, J = 7.8 Hz), 8.33 (1H, s), 9.96 (1H, s), 10.09 (1H, s).


48
δ 2.31 (6H, s), 7.45 (2H, s), 7.53-7.60 (3H, m), 7.77 (1H, d, J = 7.3 Hz), 8.06 (1H, d,



J = 8.3 Hz), 8.13 (2H, d, J = 8.3 Hz), 8.35 (1H, s), 10.01 (1H, s), 10.59 (1H, s).


52
δ 2.21 (3H, s), 2.30 (6H, s), 7.27 (1H, d, J = 8.3 Hz), 7.39-7.44 (1H, m), 7.45 (2H, s),



7.50-7.62 (2H, m), 7.70-7.52 (2H, m), 7.92 (1H, d, J = 7.8 Hz), 8.29 (1H, s),



9.99 (1H, s), 10.57 (1H, s).


54
δ 2.30 (6H, s), 3.91 (3H, s), 7.45 (2H, s), 7.56 (1H, t, J = 7.8 Hz), 7.78 (1H, d, J = 7.8 Hz), 8.03-8.15 (5H,



m), 8.36 (1H, s), 10.01 (1H, s), 10.67 (1H, s).


56
δ 2.27 (6H, s), 2.30 (6H, s), 7.18-7.22 (1H, m), 7.26-7.30 (2H, m), 7.45 (2H, s),



7.52 (1H, t, J = 7.8 Hz), 7.72 (1H, d, J = 7.8 Hz), 7.95 (1H, d, J = 7.8 Hz), 8.36 (1H, s),



9.98 (1H, s), 10.52 (1H, s).


57
δ 2.30 (6H, s), 2.33 (3H, s), 2.38 (3H, s), 7.11-7.13 (2H, m), 7.40 (1H, d, J = 7.8 Hz),



7.44 (2H, s), 7.51 (1H, t, J = 7.8 Hz), 7.72 (1H, d, J = 7.8 Hz), 7.95 (1H, d, J = 8.8 Hz),



8.34 (1H, s), 9.98 (1H, s), 10.43 (1H, s).


58
δ 2.30 (12H, s), 7.12 (2H, d, J = 7.8 Hz), 7.23-7.27 (1H, m), 7.45 (2H, s), 7.52 (1H, t,



J = 8.3 Hz), 7.75 (1H, d, J = 8.3 Hz), 7.94-7.99 (1H, m), 8.35 (1H, s), 10.00 (1H, s),



10.61 (1H, s).


59
δ 2.30 (6H, s), 7.34-7.40 (1H, m), 7.45 (2H, s), 7.50-7.58 (2H, m),



7.60-7.68 (1H, m), 7.77 (1H, d, J = 7.8 Hz), 7.96 (1H, d, J = 8.3 Hz), 8.31 (1H, s), 10.02 (1H, s),



10.78 (1H, s).


60
δ 2.30 (6H, s), 7.22-7.28 (1H, m), 7.42-7.48 (3H, m), 7.53-7.57 (1H, m),



7.75-7.82 (2H, m), 7.96 (1H, d, J = 7.8 Hz), 8.30 (1H, s), 10.01 (1H, s), 10.65 (1H, s).


61
δ 2.30 (6H, s), 7.45 (2H, s), 7.46-7.49 (2H, m), 7.53-7.59 (2H, m), 7.77 (1H, d,



J = 7.8 Hz), 7.96 (1H, d, J = 8.3 Hz), 8.30 (1H, s), 10.02 (1H, broad), 10.72 (1H, broad).


62
δ 2.30 (6H, s), 7.25-7.30 (2H, m), 7.45 (2H, s), 7.54-7.65 (2H, m), 7.77 (1H, d,



J = 7.8 Hz), 7.93 (1H, d, J = 7.8 Hz), 8.29 (1H, s), 10.03 (1H, s), 11.04 (1H, s).


66
δ 2.30 (6H, s), 7.45 (2H, s), 7.52-7.62 (2H, m), 7.66 (1H, d, J = 8.3 Hz),



7.75-7.80 (2H, m), 7.94 (1H, d, J = 7.8 Hz), 8.30 (1H, s), 10.02 (1H, s), 10.77 (1H, s).


68
δ 2.30 (6H, s), 7.45 (2H, s), 7.50-7.62 (4H, m), 7.78 (1H, d, J = 7.8 Hz), 7.94 (1H, d,



J = 7.8 Hz), 8.28 (1H, s), 10.03 (1H, s), 10.99 (1H, s).


69
δ 2.30 (6H, s), 7.45 (2H, s), 7.56 (1H, t, J = 7.8 Hz), 7.79 (1H, d, J = 7.8 Hz), 7.85 (1H, d,



J = 8.3 Hz), 7.97-8.00 (1H, m), 8.05-8.08 (1H, m), 8.27 (1H, d, J = 2.0 Hz), 8.33 (1H, s),



10.00 (1H, s), 10.61 (1H, s).


70
δ 2.74 (6H, s), 7.34 (2H, s), 7.52 (1H, t, J = 7.8 Hz), 7.81 (1H, d, J = 7.8 Hz), 7.93 (1H, d, J = 8.3 Hz),



8.13-8.15 (2H, m), 8.58 (1H, d, J = 8.3 Hz), 8.94 (1H, s), 9.27 (1H, s), 10.67 (1H, s).


71
(CDCl3) δ 1.6-2.4 (6H, broad-s), 6.5-7.7 (3H, broad), 7.8-8.0 (4H, broad), 8.10 (1H, broad-s), 8.28 (1H,



d, J = 8.8 Hz).


72
δ 2.30 (6H, s), 3.78 (6H, s), 6.66-6.75 (2H, m), 7.34-7.50 (4H, m), 7.67 (1H, d,



J = 7.8 Hz), 7.91 (1H, d, J = 7.8 Hz), 8.34 (1H, s), 9.98 (1H, s), 10.44 (1H, s).


73
δ 2.30 (6H, s), 3.83 (6H, s), 6.73 (1H, t, J = 2.4 Hz), 7.15 (2H, d, J = 2.4 Hz), 7.45 (2H, s), 7.54 (1H, t, J = 8.3 Hz),



7.75 (1H, d, J = 8.3 Hz), 8.06 (1H, d, J = 8.3 Hz), 8.33 (1H, s),



9.99 (1H, s), 10.39 (1H, s).


74
(CDCl3) δ 2.34 (6H, s), 2.68 (3H, s), 7.36 (2H, s), 7.55 (1H, t, J = 7.8 Hz), 7.62 (1H, s), 7.72 (1H, d, J = 7.8 Hz),



7.81 (1H, d, J = 8.3 Hz), 7.88 (1H, s), 7.92 (1H, d, J = 7.8 Hz), 8.05 (1H, d, J = 8.3 Hz), 8.17 (1H, s),



8.26 (1H, s).


75
δ 2.30 (6H, s), 5.22 (2H, broad-s), 6.67-6.72 (1H, m), 6.78-6.81 (1H, m),



6.97-7.02 (1H, m), 7.45 (2H, s), 7.52 (1H, t, J = 7.8 Hz), 7.72 (1H, d, J = 7.8 Hz), 7.94 (1H, d,



J = 7.8 Hz), 8.32 (1H, s), 9.98 (1H, s), 10.46 (1H, s).


77
δ 2.30 (6H, s), 7.45 (2H, s), 7.58 (1H, t, J = 7.8 Hz), 7.70 (1H, t, J = 8.8 Hz),



7.80 (1H, d, J = 7.8 Hz), 7.99 (1H, d, J = 7.8 Hz), 8.29 (1H, s), 8.45-8.50 (1H, m),



8.57-8.60 (1H, m), 10.03 (1H, s), 10.91 (1H, s).


81
δ 2.30 (6H, s), 7.56 (1H, t), 7.73-7.80 (6H, m), 7.92 (1H, d, J = 7.81 Hz), 8.22 (1H, s), 10.03 (1H, s),



11.05 (1H, s).


82
δ 2.30 (6H, s), 7.45 (2H, s), 7.57 (1H, t, J = 7.8 Hz), 7.80 (1H, d, J = 7.8 Hz), 7.92-7.96 (2H, m),



8.29-8.45 (2H, m), 8.45 (1H, m), 10.03 (1H, s), 10.98 (1H, s).


83
δ 2.28 (6H, s), 7.33-7.38 (1H, m), 7.43 (2H, s), 7.53 (1H, t, J = 7.9 Hz), 7.58 (1H, d, J = 2.4 Hz),



7.61-7.71 (1H, m), 7.75 (1H, d, J = 7.9 Hz), 7.93 (1H, d, J = 7.9 Hz), 8.28 (1H, s), 9.98 (1H, s), 10.71 (1H,



s).


84
δ 2.30 (6H, s), 7.38-7.48 (4H, m), 7.54-7.60 (2H, m), 7.78 (1H, d, J = 7.8 Hz),



7.93 (1H, d, J = 7.8 Hz), 8.28 (1H, s), 10.03 (1H, s), 11.03 (1H, s).


86
δ 2.30 (6H, s), 7.42-7.47 (3H, m), 7.55 (1H, t, J = 8.0 Hz), 7.64 (1H, d, J = 2.0 Hz), 7.66-7.77 (2H, m),



7.96 (1H, d, J = 8.0 Hz), 8.29 (1H, s), 10.01 (1H, s), 10.69 (1H, s).


87
δ 2.30 (6H, s), 7.45 (2H, s), 7.56 (1H, t, J = 7.9 Hz), 7.79 (1H, d, J = 7.9 Hz), 7.87 (1H, d, J = 7.9 Hz),



7.92 (1H, dd, J = 8.2, 1.6 Hz), 8.00 (1H, dd, J = 8.2, 1.6 Hz), 8.22 (1H, t, J = 1.6 Hz), 8.29 (1H, d, J = 1.6 Hz),



10.03 (1H, s), 10.94 (1H, s).


88
(CDCl3) δ 2.37 (6H, s), 4.06 (3H, s), 7.37 (2H, s), 7.44 (1H, d, J = 9.7 Hz), 7.52 (1H, s), 7.58 (1H, t, J = 7.8 Hz),



7.70 (1H, s), 7.74 (1H, d, J = 7.8 Hz), 7.93 (1H, s), 7.95 (1H, s), 8.02 (1H, s), 8.26 (1H, s).


89
(CDCl3) δ 2.37 (6H, s), 4.22 (3H, s), 7.37 (2H, s), 7.55 (1H, t, J = 7.8 Hz), 7.56 (1H, s), 7.72 (1H, d, J = 7.8 Hz),



7.94-7.97 (2H, m), 8.00 (1H, d, J = 7.8 Hz), 8.28 (1H, s), 8.47 (1H, d, J = 8.8 Hz), 9.83 (1H, s).


91
δ 2.25 (6H, s), 2.27 (3H, s), 2.29 (6H, s), 6.94 (2H, s), 7.45 (2H, s), 7.51 (1H, t,



J = 7.8 Hz), 7.73 (1H, d, J = 7.8 Hz), 7.94 (1H, d, J = 7.8 Hz), 8.34 (1H, s), 9.97 (1H, s),



10.53 (1H, s).


92
δ 2.33 (6H, s), 7.32-7.40 (1H, m), 7.45 (2H, s), 7.58 (1H, t, J = 8.06 Hz), 7.67-7.75 (1H, m), 7.80 (1H,



d, J = 7.81 Hz), 7.92 (1H, d, J = 8.29 Hz), 8.27 (1H, s), 10.04 (1H, s), 11.14 (1H, s).


95
δ 2.30 (6H, s), 7.45 (2H, s), 7.59 (1H, t, J = 7.8 Hz), 7.83 (1H, d, J = 7.8 Hz),



7.91-7.94 (1H, dd, J = 1.5, 7.8 Hz), 8.25 (1H, d, J = 1.5 Hz), 10.06 (1H, s), 11.27 (1H, s).


96
δ 2.30 (6H, s), 7.28-7.55 (10H, m), 7.57-7.61 (2H, m), 7.69 (1H, d, J = 7.8 Hz),



7.74 (1H, d, J = 7.8 Hz), 8.13 (1H, s), 9.94 (1H, s), 10.47 (1H, s).


97
δ 2.32 (6H, s), 7.41-7.57 (6H, m), 7.72-7.82 (3H, m), 7.85-7.88 (2H, m),



8.09-8.13 (3H, m), 8.40 (1H, s), 10.01 (1H, s), 10.53 (1H, s).


98
δ 2.31 (6H, s), 7.45 (2H, s), 7.54-7.65 (4H, m), 7.76-7.80 (2H, m), 8.01-8.06 (2H, m),



8.10 (1H, d, J = 8.3 Hz), 8.21-8.23 (1H, m), 8.43 (1H, s), 10.01 (1H, s), 10.80 (1H, s).


99
δ 2.32 (6H, s), 7.46 (2H, s), 7.57 (1H, t, J = 7.8 Hz), 7.61-7.72 (2H, m), 7.78 (1H, d,



J = 7.8 Hz), 7.99-8.17 (5H, m), 8.41 (1H, t, J = 2.0 Hz), 8.65 (1H, s), 10.01 (1H, s),



10.66 (1H, s).


100
δ 2.31 (6H, s), 7.45 (2H, s), 7.55 (1H, t, J = 7.8 Hz), 7.69-7.76 (2H, m),



8.07-8.14 (2H, m), 8.19 (1H, d, J = 7.8 Hz), 8.54 (1H, s), 8.77 (1H, d, J = 4.9 Hz), 9.99 (1H, s),



10.86 (1H, s).


101
δ 2.30 (6H, s), 7.45 (2H, s), 7.54-7.61 (2H, m), 7.78 (1H, d, J = 8.3 Hz), 8.06 (1H, d,



J = 7.3 Hz), 8.32-8.35 (2H, m), 8.77-8.79 (1H, m), 9.14 (1H, d, J = 1.5 Hz),



10.00 (1H, s), 10.66 (1H, s).


102
δ 2.30 (6H, s), 7.45 (2H, s), 7.57 (1H, t, J = 7.8 Hz), 7.80 (1H, d, J = 7.8 Hz),



7.91 (2H, d, J = 5.6 Hz), 8.06 (1H, d, J = 7.8 Hz), 8.35 (1H, s), 8.81 (2H, d, J = 5.6 Hz),



10.01 (1H, s), 10.72 (1H, s).


103
δ 2.27 (3H, s), 2.30 (6H, s), 7.45 (2H, s), 7.54-8.07 (6H, m), 8.35 (1H, s), 10.02 (1H, s), 10.77 (1H, s).


105
δ 2.30 (6H, s), 7.45 (2H, s), 7.52-7.58 (2H, m), 7.78 (1H, d, J = 8.30 Hz), 7.97 (1H, d, J = 8.29 Hz),



8.26-8.31 (2H, m), 8.42 (1H, d, J = 4.39 Hz), 10.02 (1H, s), 10.80 (1H, s).


106
δ 2.30 (6H, s), 7.45 (2H, s), 7.54-7.60 (2H, m), 7.77-7.81 (1H, m), 7.95 (1H, d,



J = 7.8 Hz), 8.10-8.13 (1H, m), 8.30 (1H, s), 8.54-8.59 (1H, m), 10.03 (1H, s),



10.88 (1H, s).


108
δ 2.31 (6H, s), 7.45 (2H, s), 7.56 (1H, t, J = 7.8 Hz), 7.78 (1H, d, J = 7.8 Hz), 7.82 (1H, dd, J = 6.3,



2.4 Hz), 8.11-8.16 (3H, m), 8.47 (1H, s), 10.01 (1H, s), 10.69 (1H, s).


109
δ 2.31 (6H, s), 7.46 (2H, s), 7.57 (1H, t, J = 8.3 Hz), 7.74 (1H, d, J = 8.3 Hz), 7.80 (1H, d, J = 8.3 Hz),



8.06 (1H, dd, J = 8.3, 1.7 Hz), 8.34 (1H, t, J = 1.7 Hz), 8.40 (1H, dd, J = 8.3, 1.7 Hz), 9.00 (1H, d, J = 1.7 Hz),



10.02 (1H, s), 10.71 (1H, s).


110
δ 2.31 (6H, s), 7.45 (2H, s), 7.56 (1H, d, J = 8.1 Hz), 7.78 (1H, d, J = 8.1 Hz), 7.86 (1H, d, J = 2.1 Hz),



8.11 (1H, dd, J = 8.1, 2.1 Hz), 8.19 (1H, d, J = 2.1 Hz), 8.53 (1H, t, J = 2.1 Hz), 8.75 (1H, d, J = 5.4 Hz),



10.01 (1H, s), 10.96 (1H, s).


111
(CDCl3) δ 2.36 (6H, s,), 7.34 (2H, s,), 7.47-8.94 (7H, m,), 9.63 (1H, s,), 10.73 (1H, s,).


113
(CDCl3) δ 2.36 (6H, s,), 7.34-8.73 (15H, m, Ar,), 10.01 (1H, s,)


114
δ 2.30 (6H, s), 2.42 (3H, s), 7.25-7.28 (1H, m), 7.44 (2H, s), 7.55 (1H, t, J = 7.8 Hz), 7.77 (1H, d, J = 7.8 Hz),



7.94-7.97 (2H, m), 8.30 (1H, s), 8.61 (1H, dd, J = 4.9, 1.5 Hz), 10.00 (1H, s), 10.67 (1H, s).


115
δ 2.29 (6H, s), 3.94 (3H, s), 4.06 (3H, s), 6.53 (1H, d, J = 8.3 Hz), 7.44 (2H, s), 7.51 (1H, t, J = 7.9 Hz),



7.72 (1H, d, J = 7.9 Hz), 7.95 (1H, d, J = 7.9 Hz), 8.12 (1H, d, J = 8.3 Hz), 8.28 (1H, s), 9.96 (1H, s),



10.07 (1H, s).


116
δ 2.29 (6H, s), 7.44 (2H, s), 7.57 (1H, t, J = 7.9 Hz), 7.80 (1H, d, J = 7.9 Hz), 8.05 (1H, d, J = 7.9 Hz),



8.30 (1H, s), 8.67 (1H, d, J = 2.2 Hz), 8.93 (1H, d, J = 2.2 Hz), 10.01 (1H, s), 10.73 (1H, s).


117
(CDCl3) δ 2.36 (6H, s), 7.37-8.50 (9H, m,), 8.97 (1H, s).


118
δ 2.28 (6H, s), 7.43 (2H, s), 7.56 (1H, t, J = 8.0 Hz), 7.74-7.79 (2H, m), 7.92 (1H, d, J = 8.0 Hz),



8.20 (1H, d, J = 8.3 Hz), 8.25 (1H, s), 10.01 (1H, s), 10.88 (1H, s).


119
(CDCl3) δ 2.36 (6H, s), 7.36-8.60 (10H, m,).


120
δ 2.31 (6H, s), 7.46 (2H, s), 7.57 (1H, t, J = 7.8 Hz), 7.80 (1H, d, J = 7.8 Hz), 8.02 (1H, d, J = 7.8 Hz),



8.08 (2H, d, J = 1.2 Hz), 8.33 (1H, t, J = 2.0 Hz), 8.40 (2H, d, J = 7.3 Hz), 10.02 (1H, s), 10.63 (1H, s).


121
δ 2.30 (6H, s), 3.89 (3H, s), 6.11 (1H, dd, J = 2.0, 3.9 Hz), 7.03 (1H, t, J = 2.0 Hz),



7.10 (1H, dd, J = 2.0, 3.9 Hz), 7.45 (2H, s), 7.49 (1H, t, J = 7.8 Hz), 7.69 (1H, d,



J = 7.8 Hz), 7.99 (1H, d, J = 7.8 Hz), 8.28 (1H, s), 9.95 (2H, s).


122
δ 2.31 (6H, s), 7.45 (2H, s), 7.57 (1H, t, J = 7.8 Hz), 7.78 (1H, d, J = 7.8 Hz),



8.11 (1H, d, J = 7.8 Hz), 8.53 (1H, s), 8.84 (1H, dd, J = 1.5, 2.4 Hz), 8.95 (1H, d, J = 2.4 Hz),



9.33 (1H, d, J = 1.5 Hz), 10.00 (1H, s), 10.97 (1H, s).


124
δ 2.28 (6H, s), 7.44 (2H, s), 7.58 (1H, t, J = 7.9 Hz), 7.81 (1H, d, J = 7.9 Hz), 7.92 (1H, d, J = 7.9 Hz),



8.20 (1H, s), 9.43 (1H, s), 9.59 (1H, s), 10.03 (1H, s), 11.06 (1H, s).


125
δ 2.30 (6H, s), 7.45 (2H, s), 7.50-7.62 (4H, m), 7.78 (1H, d, J = 7.8 Hz), 7.94 (1H, d,



J = 7.8 Hz), 8.28 (1H, s), 10.03 (1H, s), 10.99 (1H, s).


126
δ 2.30 (6H, s), 7.04 (1H, t, J = 1.5 Hz), 7.45 (2H, s), 7.53 (1H, t, J = 8.0 Hz), 7.74-7.82 (2H, m),



8.04 (1H, d, J = 1.5 Hz), 8.25 (1H, d, J = 1.5 Hz), 8.43 (1H, t, J = 1.5 Hz), 9.98 (1H, s), 10.14 (1H, s).


127
δ 1.86-1.91 (2H, m), 2.00-2.02 (1H, m), 2.19-2.29 (7H, m), 3.81-3.87 (1H, m), 3.98-4.03 (1H, m),



4.40-4.43 (1H, m), 7.44-7.50 (3H, m), 7.77 (1H, d, J = 7.8 Hz), 7.94 (1H, d, J = 7.8 Hz), 8.26 (1H, s),



9.89 (1H, s), 9.94 (1H, s).


128
(CDCl3) δ 2.02-2.10 (2H, m), 2.28 (6H, s), 3.15-3.22 (1H, m), 3.80-3.98 (4H, m), 7.44 (2H, s),



7.48 (1H, t, J = 7.8 Hz), 7.68 (1H, t, J = 7.8 Hz), 7.87 (1H, d, J = 7.8 Hz), 8.16 (1H, s), 9.96 (1H, s), 10.3 (1H,



s).


129
(CDCl3) δ 2.22 (6H, s), 7.17-7.28 (3H, m), 7.33-7.39 (2H, m), 7.42-7.48 (2H, m), 7.58-7.65 (2H, m),



7.79 (1H, dd, J = 1.5, 8.3 Hz), 7.91 (1H, s), 8.27 (1H, s), 8.51 (1H, s).


130
(CDCl3) δ 1.48-2.17 (6H, m), 2.34 (6H, s), 3.52-3.60 (1H, m), 3.92 (1H, dd, J = 2.5, 11.2 Hz),



4.11-4.18 (1H, m), 7.35 (2H, s), 7.47 (1H, t, J = 7.8 Hz), 7.60 (1H, broad), 7.69 (1H, d, J = 7.8 Hz),



7.77 (1H, dd, J = 1.0, 7.8 Hz), 8.26 (1H, s), 8.54 (1H, s).


131
δ 1.97-2.07 (2H, m), 2.15-2.31 (9H, m), 2.97-3.07 (2H, m), 3.99-3.98 (2H, m), 7.46 (2H, s), 7.55 (1H,



t, J = 8.0 Hz), 7.65 (1H, d, J = 8.0 Hz), 7.87 (1H, d, J = 8.0 Hz), 8.20 (1H, s), 9.60 (1H, s), 9.91 (1H, s).


132
(CDCl3) δ 2.35 (6H, s), 7.16 (1H, dd, J = 3.9, 4.9 Hz), 7.36 (2H, s), 7.51 (1H, t, J = 7.8 Hz), 7.59 (1H, dd, J = 1.0,



4.9 Hz), 7.67 (1H, dd, J = 1.0, 3.9 Hz), 7.70-7.74 (2H, m), 7.80-7.83 (1H, m), 7.95 (1H, s), 8.27 (1H,



s).


133
δ 2.30 (6H, s), 7.45 (2H, s), 7.54 (1H, t, J = 8.0 Hz), 7.67 (2H, d, J = 2.4 Hz), 7.75 (1H, d, J = 7.8 Hz),



8.07 (1H, d, J = 7.8 Hz), 8.31 (1H, s), 8.41 (1H, t, J = 2.2 Hz), 9.99 (1H, s), 10.28 (1H, s).


134
δ 2.30 (6H, s), 2.47 (3H, s), 7.04 (1H, d, J = 4.2 Hz), 7.45 (2H, s), 7.52 (1H, t, J = 7.8 Hz), 7.69 (1H, d, J = 4.2 Hz),



7.74 (1H, d, J = 7.8 Hz), 7.93 (1H, d, J = 7.8 Hz), 8.27 (1H, s), 9.97 (1H, s), 10.17 (1H, s).


135
δ 2.30 (6H, s), 7.45 (2H, s), 7.56 (1H, t, J = 7.8 Hz), 7.79 (1H, d, J = 7.8 Hz), 8.08 (1H, d, J = 7.8 Hz),



8.30 (1H, s), 8.71 (1H, d, J = 2.0 Hz), 8.74 (1H, d, J = 2.0 Hz), 10.01 (1H, s), 10.54 (1H, s).


136
δ 2.30 (6H, s), 2.50 (3H, s), 6.94 (1H, d, J = 3.4 Hz), 7.45 (2H, s), 7.52 (1H, t, J = 7.9 Hz), 7.74 (1H, d, J = 7.9 Hz),



7.88 (1H, d, J = 3.4 Hz), 8.02 (1H, d, J = 7.9 Hz), 8.27 (1H, s), 9.97 (1H, s), 10.32 (1H, s).


137
δ 2.29 (6H, s), 7.22 (1H, d, J = 5.1 Hz), 7.43 (2H, s), 7.53 (1H, t, J = 8.0 Hz), 7.76 (1H, d, J = 8.0 Hz),



7.91-7.93 (2H, m), 8.26 (1H, s), 9.98 (1H, s), 10.42 (1H, s).


138
δ 2.30 (6H, s), 7.45 (2H, s), 7.57 (1H, t, J = 8.1 Hz), 7.79 (1H, d, J = 8.1 Hz), 8.05 (1H, d, J = 8.1 Hz),



8.52 (1H, s), 9.97 (1H, s), 11.11 (1H, s).


139
δ 2.30 (6H, s), 7.26 (1H, d, J = 5.4 Hz), 7.45 (2H, s), 7.54 (1H, t, J = 8.0 Hz), 7.77 (1H, d, J = 8.0 Hz),



7.90-7.94 (2H, m), 8.27 (1H, s), 9.99 (1H, s), 10.50 (1H, s).


140
δ 2.30 (6H, s), 7.39 (1H, d, J = 4.6 Hz), 7.45 (2H, s), 7.54 (1H, t, J = 8.1 Hz), 7.77 (1H, d, J = 8.1 Hz),



7.92 (1H, d, J = 4.6 Hz), 8.02 (1H, d, J = 8.1 Hz), 8.26 (1H, s), 9.99 (1H, s), 10.50 (1H, s).


141
δ 2.30 (6H, s), 7.29 (1H, d, J = 4.9 Hz), 7.45 (2H, s), 7.55 (1H, t, J = 7.9 Hz), 7.77 (1H, d, J = 7.9 Hz),



7.81 (1H, d, J = 4.9 Hz), 7.92 (1H, d, J = 7.9 Hz), 8.29 (1H, s), 10.00 (1H, s), 10.50 (1H, s).


142
δ 2.27 (6H, s), 7.25-7.52 (10H, m), 7.70-7.73 (1H, m), 7.81-7.20 (1H, m), 8.12 (1H, s), 9.94 (1H, s),



10.27 (1H, s).


143
δ 2.28 (6H, s), 2.40 (3H, s), 2.45 (3H, s), 6.74 (1H, s), 7.43 (2H, s), 7.49 (1H, t, J = 8.1 Hz), 7.71 (1H,



d, J = 8.1 Hz), 7.90 (1H, d, J = 8.1 Hz), 8.24 (1H, s), 9.94 (1H, s), 9.98 (1H, s).


144
δ 2.31 (6H, s), 7.41-7.59 (5H, m), 7.78 (1H, d, J = 7.8 Hz), 8.00-8.09 (3H, m), 8.34 (1H, d, J = 2.0 Hz),



8.43 (1H, s), 10.02 (1H, s), 10.75 (1H, s).


146
δ 0.86 (3H, 7.2), 2.30 (6H, s), 4.34 (2H, q, J = 7.2 Hz), 7.45 (2H, s), 7.77-7.79 (3H, m), 7.84 (1H, s),



8.24 (1H, s), 8.37 (1H, s), 10.05 (1H, s), 11.11 (1H, s).


147
δ 2.30 (6H, s), 3.89 (3H, s), 7.45 (2H, s), 7.52 (1H, t, J = 7.9 Hz), 7.73 (1H, d, J = 7.9 Hz), 7.97 (1H, d, J = 7.9 Hz),



8.23 (1H, s), 8.45 (1H, s), 9.98 (1H, s), 10.08 (1H, s).


148
δ 2.35 (6H, s), 3.92 (3H, s), 7.26 (1H, s), 7.36 (2H, s), 7.48-7.55 (2H, m),, 7.70 (1H, d, J = 7.7 Hz),



7.83 (1H, d, J = 7.7 Hz), 8.26 (1H, s), 8.47 (1H, s).


149
δ 2.36 (6H, s), 3.95 (3H, s), 7.26 (1H, s), 7.36 (2H, s), 7.50 (1H, t, J = 7.7 Hz), 7.70 (1H, d, J = 7.7 Hz),



7.83 (1H, d, J = 7.7 Hz), 8.00 (1H, s), 8.26 (1H, s), 8.58 (1H, s).


150
(CDCl3) δ 2.35 (6H, s), 4.01 (3H, s), 7.36 (2H, s), 7.51 (1H, t, J = 7.8 Hz),



7.68-7.73 (3H, m), 7.92 (1H, s), 8.05 (1H, s), 8.25 (1H, s).


151
δ 2.29 (6H, s), 4.06 (3H, s), 7.44 (2H, s), 7.53 (1H, t, J = 7.9 Hz), 7.77 (1H, d, J = 7.9 Hz), 7.96 (1H, d, J = 7.9 Hz),



8.11 (1H, s), 8.26 (1H, s), 10.02 (1H, s), 10.58 (1H, s).


152
δ 2.30 (6H, s), 7.32 (1H, d, J = 2.0 Hz), 7.45 (2H, s), 7.58 (1H, t, J = 7.8 Hz),



7.81 (1H, d, J = 7.8 Hz), 8.04 (1H, d, J = 7.8 Hz), 8.35 (1H, s), 8.84 (1H, d, J = 2.0 Hz),



10.03 (1H, s), 10.97 (1H, s).


153
δ 2.29 (6H, s), 7.46 (2H, s), 7.64 (1H, t), 7.72 (1H, d, J = 1.0 Hz), 7.81 (1H, s), 7.97 (1H, d, J = 8.0 Hz),



8.17 (1H, s), 8.34 (1H, s), 10.04 (1H, s).


154
δ 2.29 (6H, s), 2.51 (3H, s), 2.56 (3H, s), 7.46 (2H, s), 7.53 (1H, t, J = 8.03 Hz), 7.75 (1H, d, J = 8.03 Hz),



7.92 (1H, d, J = 8.03 Hz), 8.24 (1H, s), 9.79 (1H, s), 10.30 (1H, s).


155
δ 1.36 (3H, t, J = 7.3 Hz), 2.30 (6H, s), 2.73 (3H, s), 3.05 (2H, q, J = 7.3 Hz), 7.45 (2H, s), 7.55 (1H, t, J = 8.3 Hz),



7.78 (1H, d, J = 8.3 Hz), 7.98 (1H, d, J = 8.3 Hz), 8.29 (1H, s), 10.01 (1H, s), 10.69 (1H, s).


156
δ 2.28 (6H, s), 2.57 (3H, s), 7.43 (2H, s), 7.53 (1H, t, J = 7.8 Hz), 7.77 (1H, d, J = 7.8 Hz), 7.91 (1H, d, J = 7.8 Hz),



8.21 (1H, s), 9.98 (1H, s), 10.47 (1H, s).


157
δ 2.31 (6H, s), 7.45 (2H, s), 7.57 (1H, t, J = 7.8 Hz), 7.79 (1H, d, J = 7.8 Hz), 8.06 (1H, d, J = 7.8 Hz),



8.53 (1H, s), 10.00 (1H, s), 11.12 (1H, s).


158
δ 2.36 (6H, s), 7.45 (2H, s), 7.57 (1H, t, J = 8.1 Hz), 7.79 (1H, d, J = 8.1 Hz), 8.06 (1H, d, J = 8.1 Hz),



8.53 (1H, s), 10.01 (1H, s), 11.11 (1H, s).


159
δ 2.30 (6H, s), 7.45 (2H, s), 7.56-7.66 (3H, m), 7.80 (1H, d, J = 8.3 Hz), 7.94-7.98 (2H, m),



8.16-8.20 (1H, m), 8.32 (1H, s), 10.04 (1H, s), 10.79 (1H, s).


160
δ 2.31 (6H, s), 7.45 (2H, s), 7.53-7.61 (2H, m), 7.78 (1H, d, J = 7.8 Hz), 7.92-7.95 (1H, m),



8.02-8.07 (2H, m), 8.34 (1H, s), 9.99 (1H, s), 10.50 (1H, s).


161
δ 2.30 (6H, s), 7.37 (1H, t, J = 7.8 Hz), 7.45 (2H, s), 7.57 (1H, t, J = 7.8 Hz), 7.62-7.65 (2H, m), 7.79 (1H,



d, J = 7.8 Hz), 7.99 (1H, d, J = 7.8 Hz), 8.30 (1H, s), 10.01 (1H, s), 10.65 (1H, s).


163
δ 2.38 (3H, s), 7.53-7.63 (4H, m), 7.70 (1H, s), 7.77 (1H, d, J = 7.8 Hz), 7.81 (1H, s),



7.99-8.01 (2H, m), 8.08 (1H, d, J = 7.8 Hz), 8.37 (1H, s), 10.28 (1H, s), 10.50 (1H, s).


164
(CDCl3) δ 1.20 (3H, t, J = 7.3 Hz), 2.32 (3H, s), 2.67 (2H, q, J = 7.3 Hz), 7.36 (2H, s),



7.46-7.51 (3H, m), 7.55-7.59 (1H, m), 7.67-7.72 (2H, m), 7.85-7.88 (3H, m),



8.15 (1H, s), 8.28 (1H, s).


165
δ 1.13 (3H, t, J = 7.3 Hz), 2.29 (3H, s), 2.67 (2H, q, J = 7.3 Hz), 7.33-7.41 (3H, m), 7.47 (1H, s),



7.52-7.63 (2H, m), 7.67-7.76 (2H, m), 7.97 (1H, d, J = 7.8 Hz), 8.32 (1H, s), 10.01 (1H, s), 10.65 (1H, s).


166
δ 2.36 (3H, s), 7.53-7.63 (4H, m), 7.68 (1H, s), 7.79 (1H, d, J = 7.8 Hz), 7.96 (1H, s),



7.99-8.01 (2H, m), 8.08 (1H, dd, J = 1.5, 7.8 Hz), 8.38 (1H, d, J = 1.5 Hz), 10.27 (1H, s),



10.50 (1H, s).


167
(CDCl3) δ 2.48 (3H, s), 7.05 (1H, s), 7.23 (1H, s), 7.50-7.62 (4H, m), 7.69 (1H, d, J = 7.8 Hz), 7.84 (1H, dd,



J = 2.0, 7.8 Hz), 7.89 (2H, d, J = 6.8 Hz), 8.13 (1H, s), 8.16 (1H, d, J = 6.8 Hz), 8.39 (1H, t, J = 1.9 Hz),



8.89 (1H, s).


168
δ 1.15 (3H, t, J = 7.3 Hz), 2.73 (2H, q, J = 7.3 Hz), 7.50-7.63 (5H, m), 7.71-7.77 (2H, m), 7.94-8.01 (2H,



m), 8.08 (1H, d, J = 7.8 Hz), 8.37 (1H, s), 10.28 (1H, s), 10.50 (1H, s).


169
δ 1.14 (3H, t, J = 7.3 Hz), 2.73 (2H, q, J = 7.3 Hz), 7.52-7.64 (5H, m), 7.76 (1H, d, J = 7.8 Hz), 7.83 (1H,



d, J = 2.0 Hz), 7.98-8.01 (2H, m), 8.06-8.09 (1H, m), 8.37 (1H, s), 10.29 (1H, s), 10.48 (1H, s).


170
δ 1.14 (3H, t, J = 7.3 Hz), 2.72 (2H, q, J = 7.3 Hz), 7.33-7.39 (2H, m), 7.53-7.64 (3H, m), 7.67-7.72 (1H,



m), 7.76 (1H, d, J = 7.8 Hz), 7.82 (1H, s), 7.98 (1H, d, J = 8.8 Hz), 8.32 (1H, s), 10.30 (1H, s), 10.65 (1H, s).


171
δ 1.13 (3H, t, J = 7.3 Hz), 2.71 (2H, q, J = 7.3 Hz), 7.52-7.63 (5H, m), 7.78 (1H, d, J = 7.8 Hz),



7.97-8.01 (3H, m), 8.07-8.09 (1H, m), 8.37 (1H, d, J = 2.0 Hz), 10.28 (1H, s), 10.48 (1H, s).


172
δ 1.13 (3H, t, J = 7.3 Hz), 2.71 (2H, q, J = 7.3 Hz), 7.33-7.39 (2H, m), 7.54-7.63 (3H, m), 7.67-7.72 (1H,



m), 7.78 (1H, d, J = 7.8 Hz), 7.97-8.00 (2H, m), 8.33 (1H, s), 10.30 (1H, s), 10.66 (1H, s).


173
δ 1.13 (3H, t, J = 7.3 Hz), 2.72 (2H, q, J = 7.3 Hz), 7.57-7.64 (2H, m), 7.83 (1H, d, J = 7.8 Hz), 7.98 (1H,



s), 8.10 (1H, d, J = 7.8 Hz), 8.24 (2H, d, J = 8.8 Hz), 8.37 (1H, s), 8.40 (2H, d, J = 8.8 Hz), 10.32 (1H, s),



10.81 (1H, s).


174
δ 1.13 (3H, t, J = 7.3 Hz), 2.71 (2H, q, J = 7.3 Hz), 7.56-7.63 (2H, m), 7.82 (1H, d, J = 7.8 Hz), 7.98 (1H,



s), 8.04-8.10 (3H, m), 8.15 (2H, d, J = 8.3 Hz), 8.36 (1H, s), 10.31 (1H, s), 10.72 (1H, s).


175
δ 0.85 (3H, t, J = 7.3 Hz), 1.49-1.59 (2H, m), 2.30 (3H, s), 2.65 (2H, t, J = 6.8 Hz), 7.40 (1H, s), 7.47 (1H,



s), 7.58 (1H, t, J = 7.8 Hz), 7.79 (1H, d, J = 7.8 Hz), 8.08 (1H, s), 8.22-8.25 (2H, m), 8.36-8.41 (3H, m),



10.03 (1H, s), 10.79 (1H, s).


176
δ 1.18 (6H, d, J = 6.8 Hz), 2.29 (3H, s), 3.23 (1H, septet, J = 6.8 Hz), 7.41 (1H, s), 7.47 (1H, s),



7.52-7.63 (4H, m), 7.75 (1H, d, J = 7.8 Hz), 7.99-8.01 (2H, m), 8.06-8.09 (1H, m), 8.36 (1H, t, J = 2.0 Hz),



10.00 (1H, s), 10.48 (1H, s).


177
δ 1.17 (6H, d, J = 6.8 Hz), 2.30 (3H, s), 3.24 (1H, septet, J = 6.8 Hz), 7.28-7.41 (3H, m), 7.47 (1H, s),



7.55-7.63 (2H, m), 7.65-7.78 (2H, m), 7.99 (1H, d, J = 7.8 Hz), 8.33 (1H, s), 10.02 (1H, s), 10.66 (1H, s).


178
δ 0.85 (3H, t, J = 7.3 Hz), 1.47-1.60 (2H, m), 2.70 (2H, t, J = 7.3 Hz), 7.53-7.63 (5H, m), 7.75 (1H, d, J = 7.8 Hz),



7.83 (1H, d, J = 2.0 Hz), 7.98-8.01 (2H, m), 8.08 (1H, d, J = 7.8 Hz), 8.36 (1H, s), 10.29 (1H, s),



10.49 (1H, s).


179
δ 0.85 (3H, t, J = 7.3 Hz), 1.50-1.60 (2H, m), 2.69 (2H, t, J = 6.8 Hz), 7.29-7.40 (2H, m), 7.53-7.62 (3H,



m), 7.67-7.76 (2H, m), 7.83 (1H, d, J = 2.0 Hz), 7.98 (1H, d, J = 7.8 Hz), 8.32 (1H, s), 10.31 (1H, s),



10.66 (1H, s).


180
δ 0.85 (3H, t, J = 7.3 Hz), 1.50-1.58 (2H, m), 2.70 (2H, t, J = 7.8 Hz), 7.57-7.63 (2H, m), 7.78-7.84 (2H,



m), 8.09 (1H, d, J = 7.8 Hz), 8.18-8.24 (2H, m), 8.35-8.41 (3H, m), 10.32 (1H, s), 10.80 (1H, s).


181
δ 0.85 (3H, t, J = 7.3 Hz), 1.50-1.60 (2H, m), 2.69 (2H, t, J = 7.3 Hz), 7.56-7.62 (2H, m), 7.79 (1H, d, J = 7.8 Hz),



7.83 (1H, d, J = 2.0 Hz), 8.04-8.09 (3H, m), 8.15 (2H, d, J = 8.8 Hz), 8.35 (1H, s), 10.31 (1H, s),



10.72 (1H, s).


182
δ 0.84 (3H, t, J = 7.3 Hz), 1.49-1.59 (2H, m), 2.68 (2H, t, J = 7.3 Hz), 7.53-7.63 (5H, m), 7.77 (1H, d, J = 7.8 Hz),



7.97-8.01 (3H, m), 8.08 (1H, d, J = 7.8 Hz), 8.37 (1H, s), 10.29 (1H, s), 10.49 (1H, s).


183
δ 0.84 (3H, t, J = 7.3 Hz), 1.49-1.59 (2H, m), 2.67 (2H, t, J = 7.3 Hz), 7.28-7.40 (2H, m), 7.51-7.63 (3H,



m), 7.68-7.72 (1H, m), 7.77 (1H, d, J = 8.3 Hz), 7.97-8.00 (2H, m), 8.33 (1H, s), 10.31 (1H, s), 10.67 (1H,



s).


184
δ 0.84 (3H, t, J = 7.3 Hz), 1.49-1.59 (2H, m), 2.68 (2H, t, J = 6.8 Hz), 7.57-7.62 (2H, m), 7.82 (1H, d, J = 7.8 Hz),



7.98 (1H, d, J = 2.0 Hz), 8.08-8.10 (1H, m), 8.15-8.41 (5H, m), 10.32 (1H, s), 10.80 (1H, s).


185
δ 0.84 (3H, t, J = 7.3 Hz), 1.49-1.57 (2H, m), 2.68 (2H, broad), 7.56-7.61 (2H, m), 7.81 (1H, d, J = 7.8 Hz),



7.98 (1H, s), 8.05 (2H, d, J = 8.3 Hz), 8.09 (1H, s), 8.15 (2H, d, J = 8.3 Hz), 8.35 (1H, s), 10.31 (1H,



s), 10.72 (1H, s).


186
δ 0.84 (3H, t, J = 7.3 Hz), 1.49-1.57 (2H, m), 2.68 (2H, t, J = 6.8 Hz), 7.56-7.61 (2H, m), 7.80 (1H, d, J = 7.8 Hz),



7.94 (2H, d, J = 8.3 Hz), 7.98 (1H, s), 8.09 (1H, d, J = 7.8 Hz), 8.20 (2H, d, J = 8.3 Hz), 8.36 (1H, s),



10.31 (1H, s), 10.71 (1H, s).


187
δ 0.83 (3H, t, J = 7.3 Hz), 1.21-1.31 (2H, m), 1.47-1.55 (2H, m), 2.72 (2H, t, J = 7.8 Hz), 7.53-7.63 (5H,



m), 7.70-7.75 (2H, m), 7.99-8.01 (2H, m), 8.06-8.09 (1H, m), 8.37 (1H, t, J = 2.0 Hz), 10.27 (1H, s),



10.49 (1H, s).


188
δ 0.83 (3H, t, J = 7.3 Hz), 1.21-1.31 (2H, m), 1.47-1.55 (2H, m), 2.72 (2H, t, J = 7.8 Hz), 7.33-7.40 (2H,



m), 7.53-7.63 (3H, m), 7.67-7.75 (3H, m), 7.98 (1H, d, J = 7.8 Hz), 8.32 (1H, s), 10.29 (1H, s), 10.66 (1H, s).


189
δ 0.83 (3H, t, J = 7.3 Hz), 1.21-1.31 (2H, m), 1.47-1.55 (2H, m), 2.72 (2H, t, J = 7.3 Hz), 7.52-7.63 (5H,



m), 7.75 (1H, d, J = 7.8 Hz), 7.82 (1H, d, J = 1.5 Hz), 7.99-8.01 (2H, m), 8.08 (1H, dd, J = 1.5, 7.8 Hz),



8.37 (1H, t, J = 1.5 Hz), 10.29 (1H, s), 10.49 (1H, s).


190
δ 0.83 (3H, t, J = 7.3 Hz), 1.21-1.31 (2H, m), 1.47-1.55 (2H, m), 2.71 (2H, t, J = 7.3 Hz), 7.28-7.37 (2H,



m), 7.53-7.62 (3H, m), 7.72 (1H, t, J = 7.3 Hz), 7.75 (1H, d, J = 7.8 Hz), 7.82 (1H, s), 7.98 (1H, d, J = 7.8 Hz),



8.62 (1H, s), 10.31 (1H, s), 10.66 (1H, s).


191
δ 0.82 (3H, t, J = 7.3 Hz), 1.22-1.30 (2H, m), 1.46-1.54 (2H, m), 2.70 (2H, t, J = 7.8 Hz), 7.53-7.63 (5H,



m), 7.78 (1H, d, J = 7.8 Hz), 7.93-8.02 (3H, m), 8.07-8.09 (1H, m), 8.37 (1H, s), 10.29 (1H, s), 10.49 (1H, s).


192
δ 0.83 (3H, t, J = 7.3 Hz), 1.21-1.31 (2H, m), 1.47-1.55 (2H, m), 2.71 (2H, t, J = 7.8 Hz), 7.28-7.40 (2H,



m), 7.55-7.65 (3H, m), 7.69-7.73 (1H, m), 7.79 (1H, d, J = 7.8 Hz), 7.98-8.02 (2H, m), 8.35 (1H, s),



10.33 (1H, s), 10.68 (1H, s).


193
δ 0.75 (3H, t, J = 7.3 Hz), 1.18 (3H, d, J = 6.8 Hz), 1.55-1.60 (2H, m), 3.00-3.05 (1H, m), 7.49-7.67 (5H,



m), 7.72-7.77 (2H, m), 7.99-8.02 (2H, m), 8.09 (1H, d, J = 7.8 Hz), 8.36 (1H, s), 10.29 (1H, s), 10.49 (1H, s).


194
δ 0.75 (3H, t, J = 7.3 Hz), 1.17 (3H, d, J = 6.8 Hz), 1.55-1.60 (2H, m), 2.98-3.04 (1H, m), 7.52-7.63 (5H,



m), 7.77 (1H, d, J = 8.3 Hz), 7.84 (1H, s), 7.99-8.10 (3H, m), 8.36 (1H, s), 10.30 (1H, s), 10.49 (1H, s).


195
δ 0.74 (3H, t, J = 7.3 Hz), 1.17 (3H, d, J = 6.8 Hz), 1.55-1.63 (2H, m), 2.98-3.04 (1H, m), 7.33-7.40 (2H,



m), 7.52-7.63 (3H, m), 7.67-7.77 (2H, m), 7.83 (1H, d, J = 1.5 Hz), 7.99 (1H, d, J = 8.3 Hz), 8.32 (1H, s),



10.32 (1H, s), 10.66 (1H, s).


196
δ 0.74 (3H, t, J = 6.8 Hz), 1.15 (3H, d, J = 6.8 Hz), 1.53-1.64 (2H, m), 2.94-3.04 (1H, m), 7.51-7.63 (5H,



m), 7.79 (1H, d, J = 7.3 Hz), 7.98-8.02 (3H, m), 8.09 (1H, dd, J = 1.5, 7.8 Hz), 8.37 (1H, s), 10.30 (1H, s),



10.50 (1H, s).


197
δ 7.33-7.41 (2H, m), 7.56-7.64 (2H, m), 7.68-7.73 (2H, m), 7.93-8.03 (2H, m), 8.38-8.40 (1H, m),



8.45 (1H, d, J = 2.0 Hz), 10.72 (1H, s), 10.98 (1H, s).


198
δ 2.50 (3H, s), 7.39 (1H, s), 7.48-7.63 (4H, m), 7.73 (1H, s), 7.77 (1H, d, J = 7.8 Hz), 7.99-8.01 (2H, m),



8.08 (1H, d, J = 7.8 Hz), 8.35 (1H, s), 10.36 (1H, s), 10.50 (1H, s).


199
δ 2.50 (3H, s), 7.33-7.39 (3H, m), 7.53-7.63 (2H, m), 7.67-7.77 (3H, m), 7.98 (1H, d, J = 7.8 Hz),



8.30 (1H, s), 10.38 (1H, s), 10.67 (1H, s).


200
δ 2.81 (3H, s), 7.53-7.64 (4H, m), 7.75 (1H, d, J = 8.3 Hz), 7.99-8.01 (2H, m), 8.08-8.11 (2H, m),



8.25 (1H, d, J = 2.0 Hz), 8.40 (1H, t, J = 2.0 Hz), 10.52 (1H, s), 10.61 (1H, s).


201
δ 3.40 (3H, s), 7.33-7.40 (2H, m), 7.56-7.63 (2H, m), 7.67-7.78 (2H, m), 7.99 (1H, d, J = 8.3 Hz),



8.17 (1H, d, J = 1.5 Hz), 8.35 (1H, s), 8.39 (1H, d, J = 1.5 Hz), 10.63 (1H, s), 10.69 (1H, s).


202
δ 3.40 (3H, s), 7.57-7.62 (2H, m), 7.79 (1H, d, J = 7.8 Hz), 7.96 (1H, dd, J = 1.5, 8.3 Hz), 8.12 (1H, dd, J = 1.5,



8.3 Hz), 8.17 (1H, d, J = 2.0 Hz), 8.32 (1H, d, J = 2.0 Hz), 8.40 (1H, d, J = 2.0 Hz), 8.54-8.56 (1H, m),



10.65 (1H, s), 10.92 (1H, s).


203
δ 3.40 (3H, s), 7.53-7.63 (4H, m), 7.78 (1H, d, J = 7.8 Hz), 7.98-8.01 (2H, m), 8.07-8.10 (1H, m),



8.21 (1H, s), 8.39 (1H, s), 8.48 (1H, d, J = 1.5 Hz), 10.51 (1H, s), 10.63 (1H, s).


204
δ 3.39 (3H, s), 7.33-7.40 (2H, m), 7.56-7.63 (2H, m), 7.68-7.72 (1H, m), 7.78 (1H, d, J = 7.8 Hz),



8.00 (1H, d, J = 7.8 Hz), 8.21 (1H, d, J = 1.5 Hz), 8.35 (1H, s), 8.48 (1H, d, J = 1.5 Hz), 10.66 (1H, s),



10.69 (1H, s).


205
δ 3.39 (3H, s), 7.36-7.42 (2H, m), 7.58 (1H, t, J = 7.8 Hz), 7.78 (1H, d, J = 7.8 Hz), 8.06-8.10 (3H, m),



8.21 (1H, s), 8.36 (1H, s), 8.48 (1H, s), 10.52 (1H, s), 10.63 (1H, s).


206
δ 3.39 (3H, s), 7.61 (1H, t, J = 7.8 Hz), 7.82 (1H, d, J = 7.8 Hz), 8.09 (1H, d, J = 7.8 Hz), 8.20-8.24 (3H,



m), 8.37-8.41 (3H, m), 8.48 (1H, s), 10.67 (1H, s), 10.83 (1H, s).


207
δ 3.39 (3H, s), 7.60 (1H, t, J = 7.8 Hz), 7.81 (1H, d, J = 7.8 Hz), 7.97-8.10 (3H, m), 8.14-8.21 (3H, m),



8.37 (1H, t, J = 2.0 Hz), 8.48 (1H, d, J = 2.0 Hz), 10.65 (1H, s), 10.74 (1H, s).


208
δ 3.39 (3H, s), 7.57-7.62 (2H, m), 7.80 (1H, d, J = 7.8 Hz), 7.96 (1H, dd, J = 1.5, 7.8 Hz), 8.11 (1H, dd, J = 1.5,



7.8 Hz), 8.20 (1H, s), 8.31 (1H, s), 8.51 (1H, s), 8.55 (1H, dd, J = 1.5, 4.9 Hz), 10.68 (1H, s), 10.92 (1H,



s).


209
δ 1.96 (3H, s), 3.84 (2H, broad), 7.53-7.63 (4H, m), 7.73 (1H, d, J = 7.8 Hz), 7.89 (1H, s), 7.99-8.01 (2H,



m), 8.07 (1H, dd, J = 1.5, 7.8 Hz), 8.19 (1H, s), 8.33 (1H, t, J = 2.0 Hz), 10.43 (1H, s), 10.49 (1H, s).


210
δ 7.53-7.64 (4H, m), 7.81 (1H, d, J = 7.8 Hz), 8.00-8.05 (3H, m), 8.11 (1H, d, J = 7.8 Hz), 8.31 (1H, d, J = 1.5 Hz),



8.41 (1H, s), 10.52 (1H, s), 10.93 (1H, s).


211
δ 2.29 (6H, s), 7.47 (2H, s), 7.50-7.62 (4H, m), 7.75 (1H, d, J = 7.8 Hz), 7.97-8.00 (2H, m), 8.05 (1H, dd,



J = 1.5, 7.8 Hz), 8.36 (1H, s), 10.01 (1H, s), 10.46 (1H, s).


212
δ 2.30 (6H, s), 7.45 (2H, s), 7.51-7.63 (4H, m), 7.76 (1H, d, J = 7.8 Hz), 7.98-8.07 (3H, m), 8.37 (1H, d,



J = 2.0 Hz), 9.99 (1H, s), 10.48 (1H, s).


255
δ 7.25-7.29 (2H, m), 7.54-7.65 (2H, m), 7.78 (1H, d, J = 7.8 Hz), 7.92-7.95 (1H, m), 8.03 (2H, s),



8.30 (1H, s), 10.58 (1H, s), 11.05 (1H, s).


256
δ 7.53-7.63 (4H, m), 7.78 (1H, d, J = 7.3 Hz), 7.99-8.01 (2H, m), 8.06-8.09 (1H, m), 8.17 (2H, s),



8.38 (1H, s), 10.50 (1H, s), 10.55 (1H, s).


257
δ 7.25-7.29 (2H, m), 7.55-7.63 (2H, m), 7.79 (1H, d, J = 7.3 Hz), 7.94 (1H, d, J = 8.3 Hz), 8.17 (2H, s),



8.30 (1H, s), 10.60 (1H, s), 11.05 (1H, s).


258
(CDCl3) δ 7.45-7.61 (4H, m), 7.76 (1H, d, J = 7.8 Hz), 7.84-7.91 (3H, m), 7.93 (2H, s), 8.02 (1H, s),



8.08 (1H, d, J = 6.8 Hz), 8.31 (1H, s).


259
(CDCl3) δ 7.22 (1H, dd, J = 7.8, 12.2 Hz), 7.35 (1H, t, J = 7.8 Hz), 7.52-7.60 (2H, m), 7.77 (1H, d,



J = 7.8 Hz), 7.88 (1H, s), 7.92 (1H, s), 7.93 (2H, d), 8.19 (1H, dt, J = 1.9, 7.8 Hz), 8.33 (1H, s), 8.64 (1H, d,



J = 15.6 Hz).


260
(CDCl3) δ 2.31 (6H, s), 7.41 (2H, s), 7.50-7.67 (5H, m), 7.71 (1H, d, J = 7.8 Hz), 7.87-7.90 (3H, m),



8.07 (1H, s), 8.31 (1H, s).


261
(CDCl3) δ 2.33 (6H, s), 7.20-7.25 (1H, m), 7.35 (1H, t, J = 7.3 Hz), 7.44 (2H, s), 7.52-7.60 (3H, m),



7.73 (1H, d, J = 7.8 Hz), 7.88 (1H, dd, J = 1.0, 7.8 Hz), 8.18 (1H, dt, J = 2.0, 7.8 Hz), 8.33 (1H, s), 8.63 (1H, d,



J = 7.3 Hz).


262
(CDCl3) δ 7.44-7.57 (5H, m), 7.72 (2H, s), 7.78 (1H, d, J = 7.8 Hz), 8.00 (1H, d, J = 6.8 Hz), 8.18 (1H, d,



J = 8.3 Hz), 8.34 (1H, t, J = 2.0 Hz), 9.46 (1H, s), 9.83 (1H, s).


263
(CDCl3) δ 7.47-7.57 (4H, m), 7.78 (1H, d, J = 7.8 Hz), 7.93 (2H, s), 7.99-8.01 (2H, m), 8.18 (1H, d,



J = 7.8 Hz), 8.33 (1H, t, J = 2.0 Hz), 9.27 (1H, s), 9.65 (1H, s).


266
δ 7.20-7.25 (1H, m), 7.35 (1H, t, J = 7.8 Hz), 7.53-7.60 (2H, m), 7.76-7.79 (2H, m), 7.95 (2H, s), 7.96 (1H,



s), 8.19 (1H, dt, J = 2.0, 7.8 Hz), 8.32 (1H, s), 8.63 (1H, d, J = 15.7 Hz).


276
(CDCl3) δ 7.56 (1H, t, J = 7.8 Hz), 7.71 (1H, d, J = 7.8 Hz), 7.75 (1H, d, J = 7.8 Hz), 7.87-7.90 (3H, m),



8.04 (1H, d, J = 7.8 Hz), 8.28 (2H, s), 8.42 (1H, dd, J = 1.0, 7.3 Hz), 8.46 (1H, s), 8.76 (1H, t, J = 2.0 Hz).


284
(CDCl3) δ 7.03 (2H, t, J = 7.8 Hz), 7.42-7.49 (1H, m), 7.54 (1H, t, J = 7.8 Hz), 7.78 (1H, d, J = 7.8 Hz),



7.81 (1H, s), 7.87-7.92 (2H, m), 7.93 (2H, s), 8.28 (1H, t, J = 2.0 Hz).


285
δ 6.86 (1H, d, J = 8.8 Hz), 7.24 (1H, t, J = 7.8 Hz), 7.30-7.32 (2H, m), 7.47 (1H, t, J = 7.8 Hz), 7.77 (1H,



d, J = 7.8 Hz), 7.93 (2H, s), 8.14 (1H, d, J = 7.3 Hz), 8.31 (1H, s), 9.32 (1H, s), 9.46 (1H, s).


286
δ 2.17 (3H, s), 7.40 (1H, t, J = 7.8 Hz), 7.49 (1H, t, J = 7.8 Hz), 7.80 (1H, d, J = 7.8 Hz), 7.78 (1H, d, J = 7.8 Hz),



7.94-7.95 (3H, m), 8.06 (1H, s), 8.16 (1H, d, J = 7.8 Hz), 8.31 (1H, s), 9.50 (1H, s), 9.58 (1H, s),



9.79 (1H, s).


287
δ 3.00 (3H, s), 7.42 (1H, t, J = 7.8 Hz), 7.50 (1H, t, J = 7.8 Hz), 7.48 (1H, s), 7.74 (1H, d, J = 7.8 Hz),



7.79 (1H, d, J = 7.8 Hz), 7.88 (1H, t, J = 2.0 Hz), 7.93 (2H, s), 8.17 (1H, d, J = 7.8 Hz), 8.29 (1H, t, J = 2.0 Hz),



9.37 (1H, s), 9.49 (1H, s), 9.72 (1H, s).


288
(CDCl3) δ 7.51 (1H, t, J = 7.8 Hz), 7.69 (1H, d, J = 7.8 Hz), 7.86-7.91 (3H, m), 7.95 (2H, s), 8.07 (1H, s),



8.39 (1H, s), 8.53-8.55 (1H, m), 8.90 (1H, s).


289
(CDCl3) δ 7.54 (1H, t, J = 8.3 Hz), 7.80 (1H, d, J = 7.8 Hz), 7.94 (2H, s), 8.02 (1H, d, J = 8.3 Hz),



8.26-8.27 (2H, m), 8.52 (1H, d, J = 8.3 Hz), 8.74 (1H, s), 8.87 (1H, s), 10.56 (1H, s).


290
δ 2.68 (3H, s), 7.52 (1H, t, J = 7.8 Hz), 7.81 (1H, d, J = 7.8 Hz), 7.93 (2H, s), 8.03 (2H, s), 8.07 (1H, s),



8.24 (1H, d, J = 7.8 Hz), 8.29 (1H, s), 9.34 (1H, s), 10.13 (1H, s).


291
(CDCl3) δ 4.17 (2H, s), 6.80-6.84 (1H, m), 6.98 (1H, dd, J = 7.8, 11.2 Hz), 7.33 (1H, dd, J = 2.9, 6.4 Hz),



7.51 (1H, t, J = 7.8 Hz), 7.82 (1H, d, J = 7.8 Hz), 7.94 (2H, s), 8.10 (1H, d, J = 8.2 Hz), 8.22 (1H, s),



9.06 (1H, d, J = 13.2 Hz), 9.48 (1H, s).


292
(CDCl3) δ 7.44 (1H, dd, J = 8.8, 10.7 Hz), 7.58 (1H, t, J = 7.8 Hz), 7.80 (1H, d, J = 7.8 Hz), 7.85 (1H, s),



7.95 (2H, s), 7.98 (1H, d, J = 7.8 Hz), 8.27 (1H, s), 8.43-8.47 (1H, m), 8.55 (1H, d, J = 14.2 Hz), 9.09 (1H,



dd, J = 3.0, 6.4 Hz).


293
δ 2.97 (3H, s), 7.16 (1H, dd, J = 8.8, 10.8 Hz), 7.49 (1H, t, J = 7.8 Hz), 7.51 (1H, s), 7.83 (1H, d, J = 7.8 Hz),



7.90-7.93 (1H, m), 7.94 (2H, s), 8.10 (1H, d, J = 7.8 Hz), 8.24 (1H, s), 9.15 (1H, d, J = 11.2 Hz),



9.38 (1H, s), 9.58 (1H, s).


294
(CDCl3) δ 4.22 (3H, s), 7.56 (1H, t, J = 7.8 Hz), 7.75 (1H, t, J = 7.8 Hz), 7.83 (1H, s), 7.94 (1H, s),



7.95 (2H, s), 7.99-8.05 (2H, m), 8.25 (1H, s), 8.47 (1H, d, J = 7.8 Hz), 9.83 (1H, s).


295
δ 4.06 (3H, s), 7.52 (1H, t, J = 7.3 Hz), 7.73 (1H, d, J = 8.3 Hz), 7.82-7.88 (2H, m), 7.89 (1H, d, J = 8.3 Hz),



7.93 (2H, s), 8.25-8.29 (2H, m), 9.48 (1H, s), 10.23 (1H, s).


296
(CDCl3) δ 2.16 (3H, s), 7.14 (1H, dd, J = 9.3, 11.2 Hz), 7.52 (1H, t, J = 7.8 Hz), 7.80 (1H, d, J = 7.8 Hz),



7.94 (2H, s), 7.96 (1H, d, J = 2.9 Hz), 8.01 (1H, d, J = 7.8 Hz), 8.13-8.16 (1H, m), 8.27 (1H, s), 8.86 (1H, s),



8.90 (1H, d, J = 14.2 Hz), 9.00 (1H, s).


306
(CDCl3) δ 7.52-7.58 (2H, m), 7.77 (1H, d, J = 7.8 Hz), 7.90 (1H, s), 7.94 (2H, s), 7.95 (1H, d, J = 7.8 Hz),



8.01-8.03 (1H, m), 8.31 (1H, d, J = 7.8 Hz), 8.47 (1H, s), 8.65 (1H, dd, J = 1.0, 4.9 Hz), 10.25 (1H, s).


307
(CDCl3) δ 7.57 (1H, t, J = 7.8 Hz), 7.73-7.77 (3H, m), 7.84 (1H, s), 7.89 (2H, s), 8.05 (1H, d, J = 7.8 Hz),



8.26 (1H, s), 8.32 (1H, s), 8.81 (1H, s), 8.83 (1H, s).


309
(CDCl3) δ 7.44 (1H, dd, J = 4.8, 7.8 Hz), 7.56 (1H, t, J = 7.8 Hz), 7.80 (1H, d, J = 7.8 Hz), 7.86 (1H, s),



7.92 (1H, d, J = 7.3 Hz), 7.95 (2H, s), 8.23 (1H, dd, J = 20., 7.9 Hz), 8.30 (1H, s), 8.41 (1H, s), 8.55 (1H, dd,



J = 2.0, 4.5 Hz).


310
(CDCl3) δ 7.46 (1H, d, J = 8.3 Hz), 7.55 (1H, t, J = 8.3 Hz), 7.74 (1H, d, J = 8.3 Hz), 7.88 (3H, s),



8.03 (1H, d, J = 7.8 Hz), 8.18 (1H, dd, J = 3.0, 8.2 Hz), 8.24 (1H, s), 8.41 (1H, s), 8.90 (1H, d, J = 2.4 Hz).


312
(CDCl3) δ 7.57 (1H, t, J = 7.8 Hz), 7.70 (2H, s), 7.75 (1H, d, J = 7.8 Hz), 7.83 (1H, s), 7.88 (2H, s),



8.04 (1H, d, J = 7.8 Hz), 8.21 (1H, s), 8.47 (1H, s).


313
(CDCl3) δ 7.33 (1H, t, J = 7.8 Hz), 7.46 (1H, d, J = 8.3 Hz), 7.60 (1H, s), 7.76 (1H, s), 7.80 (1H, d, J = 7.8 Hz),



7.95 (2H, s), 8.18-8.23 (2H, m), 8.40 (1H, s).


314
(CDCl3) δ 2.62 (3H, s), 7.29 (1H, s), 7.56 (1H, t, J = 7.8 Hz), 7.77-7.79 (2H, m), 7.91 (1H, s), 7.94 (2H, s),



8.16 (1H, d, J = 7.8 Hz), 8.29 (1H, s), 8.48 (1H, s).


315
(CDCl3) δ 7.47-7.59 (3H, m), 7.80 (1H, d, J = 7.8 Hz), 7.93 (1H, s), 7.94 (2H, s), 8.26 (1H, s), 8.34 (1H,



d, J = 6.5 Hz), 8.47 (1H, t, J = 2.0 Hz), 8.52-8.55 (1H, m), 13.91 (1H, s).


316
(CDCl3) δ 7.59 (1H, t, J = 7.8 Hz), 7.79 (1H, d, J = 7.8 Hz), 7.84 (1H, s), 7.95 (2H, s), 8.04 (1H, d, J = 7.8 Hz),



8.41 (1H, t, J = 2.0 Hz), 8.63 (1H, t, J = 2.5 Hz), 8.86 (1H, d, J = 2.4 Hz), 9.54 (1H, d, J = 1.5 Hz),



9.87 (1H, s).


317
(CDCl3) δ 3.93 (3H, s), 7.53 (1H, t, J = 7.8 Hz), 7.74 (1H, d, J = 7.8 Hz), 7.84 (1H, s), 7.87 (1H, d, J = 7.8 Hz),



7.94 (2H, s), 8.03 (1H, s), 8.26 (1H, t, J = 2.0 Hz), 8.48 (1H, s).


318
(CDCl3) δ 4.02 (3H, s), 7.53 (1H, t, J = 7.8 Hz), 7.45 (1H, d, J = 7.8 Hz), 7.80 (1H, d, J = 7.8 Hz),



7.85 (1H, s), 7.89 (1H, s), 7.94 (2H, s), 8.05 (1H, s), 8.24 (1H, s).


319
(CDCl3) δ 4.10 (3H, s), 7.53 (1H, t, J = 7.8 Hz), 7.67 (1H, s), 7.76 (1H, d, J = 7.8 Hz), 7.70-7.86 (3H, m),



7.94 (2H, s), 8.21 (1H, s).


320
(CDCl3) δ 1.94-2.04 (2H, m), 2.17-2.22 (1H, m), 2.37-2.42 (1H, m), 3.95-4.00 (1H, m), 4.05-4.09 (1H,



m), 4.49 (1H, dd, J = 5.9, 8.3 Hz), 7.50 (1H, t, J = 7.8 Hz), 7.72 (1H, d, J = 7.8 Hz), 7.83 (1H, dd, J = 2.0,



7.8 Hz), 7.87 (1H, s), 7.94 (2H, s), 8.23 (1H, t, J = 2.0 Hz), 8.67 (1H, s).


321
(CDCl3) δ 7.51-7.53 (3H, m), 7.57 (1H, t, J = 8.3 Hz), 7.76 (1H, d, J = 7.3 Hz), 7.83 (1H, s), 7.95 (2H, s),



8.01-8.07 (3H, m), 8.23 (1H, s), 8.38 (1H, s), 9.51 (1H, s).


327
(CDCl3) δ 7.45-7.61 (4H, m), 7.77 (1H, d, J = 7.8 Hz), 7.84-7.91 (3H, m), 7.97-8.18 (4H, m), 8.31 (1H,



s).


328
(CDCl3) δ 7.24 (1H, d, J = 7.8 Hz), 7.35 (1H, t, J = 7.8 Hz), 7.54-7.60 (2H, m), 7.78 (1H, d, J = 7.8 Hz),



7.89 (1H, s), 7.96 (1H, d, J = 7.8 Hz), 8.15-8.19 (3H, m), 8.33 (1H, s), 8.64 (1H, d, J = 15.6 Hz).


329
(CDCl3) δ 7.44-7.57 (4H, m), 7.70 (2H, s), 7.78 (1H, d, J = 7.8 Hz), 8.01 (2H, d, J = 6.8 Hz), 8.17 (1H, dd,



J = 1.0, 7.8 Hz), 8.34 (1H, t, J = 2.0 Hz), 9.45 (1H, s), 9.81 (1H, s).


330
(CDCl3) δ 7.22 (1H, dd, J = 8.3, 12.2 Hz), 7.34 (1H, t, J = 7.3 Hz), 7.52-7.67 (2H, m), 7.72 (2H, s), 7.76 (1H,



d, J = 7.9 Hz), 7.90 (1H, s), 7.92 (1H, s), 8.18 (1H, dt, J = 1.4, 7.8 Hz), 8.33 (1H, t, J = 2.0 Hz), 8.64 (1H, d,



J = 16.6 Hz).


331
(CDCl3) δ 7.44 (1H, dd, J = 4.4, 7.8 Hz), 7.57 (1H, t, J = 7.8 Hz), 7.73 (2H, s), 7.78 (1H, d, J = 7.8 Hz),



7.84 (1H, s), 7.90 (1H, d, J = 7.8 Hz), 8.23 (1H, dd, J = 2.0, 7.8 Hz), 8.29 (1H, s), 8.41 (1H, s), 8.55 (1H, dd,



J = 2.0, 4.9 Hz).


332
δ 7.43-7.57 (4H, m), 7.79 (1H, d, J = 7.8 Hz), 7.92 (2H, s), 8.00 (2H, d, J = 6.9 Hz), 8.18 (1H, d, J = 8.3 Hz),



8.35 (1H, t, J = 2.0 Hz), 8.59 (1H, s), 9.86 (1H, s).


333
(CDCl3) δ 7.30-7.62 (4H, m), 7.75 (1H, d, J = 7.8 Hz), 7.84 (1H, d, J = 7.8 Hz), 7.89-7.92 (3H, m), 7.93 (2H,



s), 8.03 (1H, s), 8.31 (1H, s).


334
(CDCl3) δ 7.20-7.25 (1H, m), 7.35 (1H, t, J = 6.3 Hz), 7.54-7.58 (2H, m), 7.79 (1H, d, J = 6.3 Hz),



7.90-7.94 (2H, m), 7.95 (2H, s), 8.19 (1H, t, J = 8.3 Hz), 8.33 (1H, t, J = 2.0 Hz), 8.64 (1H, d, J = 16.1 Hz).


335
(CDCl3) δ 7.51-7.62 (4H, m), 7.77 (1H, d, J = 7.3 Hz), 7.89-7.93 (3H, m), 8.02 (2H, s), 8.08 (1H, s),



8.26 (1H, s), 8.37 (1H, d, J = 14.6 Hz).


338
(CDCl3) δ 7.22 (1H, t, J = 7.8 Hz), 7.36 (1H, t, J = 7.8 Hz), 7.54-7.60 (2H, m), 7.78 (1H, d, J = 7.8 Hz),



7.90 (1H, d, J = 7.8 Hz), 8.03-8.04 (2H, m), 8.19 (1H, t, J = 7.8 Hz), 8.26 (1H, s), 8.41 (1H, s), 8.65 (1H, d,



J = 16.6 Hz).


369
(CDCl3) δ 7.46 (1H, dd, J = 4.4, 7.8 Hz), 7.59 (1H, t, J = 8.3 Hz), 7.81 (1H, d, J = 8.3 Hz),



7.89-7.92 (1H, m), 8.04 (2H, s), 8.24 (1H, dd, J = 2.0, 7.8 Hz), 8.27 (1H, s), 8.35 (1H, d, J = 13.7 Hz),



8.42 (1H, s), 8.56 (1H, dd, J = 1.4, 4.4 Hz).


375
δ 7.25 (1H, d, J = 8.3 Hz), 7.27 (1H, d, J = 7.8 Hz), 7.56-7.64 (2H, m), 7.79 (1H, d, J = 7.8 Hz), 7.94 (1H,



d, J = 8.3 Hz), 8.32 (1H, s), 8.42 (2H, s), 10.87 (1H, s), 11.05 (1H, s).


376
δ 7.53-7.64 (4H, m), 7.80 (1H, d, J = 7.8 Hz), 7.99-8.01 (2H, m), 8.09 (1H, dd, J = 1.5, 7.8 Hz), 8.41 (1H,



d, J = 1.5 Hz), 8.54 (2H, s), 10.52 (1H, s), 10.83 (1H, s).


377
δ 7.19-7.30 (2H, m), 7.57-7.66 (2H, m), 7.81 (1H, d, J = 7.8 Hz), 7.95 (1H, dd, J = 1.5, 7.8 Hz), 8.33 (1H,



t, J = 1.5 Hz), 8.53 (2H, s), 10.89 (1H, s), 11.08 (1H, s).


378
(CDCl3) δ 7.21-7.23 (1H, m), 7.36 (1H, t, J = 6.9 Hz), 7.55-7.59 (2H, m), 7.79 (1H, d, J = 8.3 Hz), 7.84 (1H,



d, J = 8.0 Hz), 8.05 (2H, s), 8.17-8.21 (2H, m), 8.43 (1H, t, J = 2.0 Hz), 8.65 (1H, d, J = 6.9 Hz).


379
(CDCl3) δ 7.46-7.63 (4H, m), 7.77 (1H, d, J = 7.8 Hz), 7.84-7.91 (3H, m), 8.00 (1H, s), 8.07 (2H, s),



8.14 (1H, s), 8.40 (1H, t, J = 2.0 Hz).


380
(CDCl3) δ 7.52-7.63 (4H, m), 7.77 (1H, d, J = 7.8 Hz), 7.89 (1H, s), 7.90 (2H, d, J = 7.8 Hz), 7.99 (1H,



s), 8.03 (1H, s), 8.26 (2H, s), 8.39 (1H, t, J = 2.0 Hz).


383
(CDCl3) δ 7.21 (1H, d, J = 8.3 Hz), 7.36 (1H, t, J = 7.8 Hz), 7.55-7.61 (2H, m), 7.78 (1H, d, J = 7.8 Hz),



7.90 (1H, d, J = 8.3 Hz), 8.02 (1H, s), 8.19 (1H, dt, J = 1.9, 8.3 Hz), 8.27 (2H, s), 8.41 (1H, s), 8.65 (1H, d, J = 16.6 Hz).


414
(CDCl3) δ 7.44 (1H, dd, J = 4.9, 7.8 Hz), 7.59 (1H, t, J = 8.3 Hz), 7.81 (1H, d, J = 7.8 Hz), 7.89 (1H, d, J = 8.3 Hz),



8.04 (1H, s), 8.23 (1H, dd, J = 1.9, 7.8 Hz), 8.27 (2H, s), 8.37 (1H, s), 8.43 (1H, s), 8.55 (1H, dd,



J = 1.9, 4.3 Hz).


460
δ 7.25 (1H, d, J = 8.3 Hz), 7.27 (1H, d, J = 7.8 Hz), 7.56-7.64 (2H, m), 7.79 (1H, d, J = 7.8 Hz), 7.94 (1H,



d, J = 8.3 Hz), 8.32 (1H, s), 8.42 (2H, s), 10.87 (1H, s), 11.05 (1H, s).


461
(CDCl3) δ 2.47 (3H, s), 7.51-7.62 (5H, m), 7.75 (1H, d, J = 7.8 Hz), 7.89-7.93 (4H, m), 8.00 (1H,



broad-s), 8.35 (1H, t, J = 2.0 Hz).


462
(CDCl3) δ 2.47 (3H, s), 7.20-7.23 (1H, m), 7.36 (1H, t, J = 7.8 Hz), 7.55-7.60 (3H, m), 7.76 (1H, d, J = 7.8 Hz),



7.89 (1H, s), 7.92 (1H, s), 8.18-8.22 (1H, m), 8.39 (1H, s), 8.62 (1H, broad-s).


463
(CDCl3) δ 2.27 (3H, s), 2.41 (3H, s), 6.59 (1H, septet, J = 6.4 Hz), 6.72 (1H, s), 7.49-7.61 (5H, m),



7.70 (1H, d, J = 7.8 Hz), 7.83-7.89 (3H, m), 8.05 (1H, broad-s), 8.33 (1H, t, J = 1.5 Hz).


464
(CDCl3) δ 2.38 (3H, s), 6.34 (1H, septet, J = 6.4 Hz), 6.87 (1H, s), 7.50-7.63 (5H, m), 7.72 (1H, d, J = 7.8 Hz),



7.88-7.90 (3H, m), 7.99 (1H, brs), 8.31 (1H, broad-s).


465
(CDCl3) δ 2.37 (3H, s), 6.36 (1H, septet, J = 5.9 Hz), 6.87 (1H, s), 7.50-7.61 (4H, m), 7.72-7.73 (2H,



m), 7.88-7.90 (3H, m), 8.06 (1H, broad-s), 8.32 (1H, s).


466
(CDCl3) δ 2.39 (3H, s), 6.36 (1H, septet, J = 5.9 Hz), 6.89 (1H, s), 7.20-7.25 (1H, m), 7.35 (1H, t, J = 6.8 Hz),



7.52-7.60 (2H, m), 7.70 (1H, broad-s), 7.75 (1H, d, J = 7.8 Hz), 7.89 (1H, d, J = 7.8 Hz),



8.17-8.21 (1H, m), 8.36 (1H, s), 8.64 (1H, broad-d, J = 16.1 Hz).


467
(CDCl3) δ 2.53 (3H, s), 6.35 (1H, septet, J = 5.9 Hz), 6.83 (1H, s), 7.49-7.61 (4H, m), 7.66 (1H, s),



7.74 (1H, d, J = 8.3 Hz), 7.88-7.92 (3H, m), 8.32 (1H, broad-s), 8.33 (1H, t, J = 1.9 Hz).


601
δ 2.34 (6H, s), 7.37 (1H, t, J = 7.8 Hz), 7.45 (2H, s), 7.53-7.65 (4H, m),



7.77-7.82 (1H, m), 8.00-8.02 (2H, m), 10.10 (1H, s), 10.29 (1H, s).


602
δ 2.36 (6H, s), 2.56 (3H, s), 7.29-7.43 (7H, m), 7.55-7.57 (1H, m), 7.75-7.78 (1H, m), 7.84-7.88 (1H,



m), 8.64-8.66 (1H, m).


603
δ 2.37 (6H, s), 2.46 (3H, s), 7.34-7.42 (5H, m), 7.69-7.85 (4H, m), 8.11 (1H, s), 8.59-8.63 (1H, s).


604
δ 2.38 (6H, s), 2.45 (3H, s), 7.33-7.38 (5H, m), 7.78-7.85 (4H, m), 8.10 (1H, s), 8.61-8.65 (1H, m).


605
δ 2.34 (6H, s), 7.39 (1H, t, J = 7.4 Hz), 7.44 (2H, s), 7.50-7.54 (1H, m), 7.76-7.80 (2H, m), 7.88 (1H, t,



J = 7.4 Hz), 8.12 (1H, t, J = 7.4 Hz), 8.20 (1H, d, J = 1.0 Hz), 10.12 (1H, s), 10.73 (1H, s).


606
δ 2.35 (6H, s), 7.40 (1H, t, J = 7.8 Hz), 7.45 (2H, s), 7.59-7.62 (1H, m), 7.82-7.90 (2H, m),



8.44-8.50 (2H, m), 8.86 (1H, d, J = 2.0 Hz), 10.12 (1H, s), 10.72 (1H, s).


607
δ 2.34 (6H, s), 7.40 (1H, t, J = 7.8 Hz), 7.45 (2H, s), 7.57-7.62 (1H, m), 7.81-7.85 (1H, m),



8.22-8.25 (2H, m), 8.39-8.42 (2H, m), 10.12 (1H, s), 10.66 (1H, s).


609
δ 2.34 (6H, s), 7.39 (1H, t, J = 6.9 Hz), 7.45 (2H, s), 7.58 (1H, t, J = 6.9 Hz), 7.82 (1H, t, J = 6.9 Hz),



8.06 (2H, d, J = 8.8 Hz), 8.15 (2H, d, J = 8.8 Hz), 10.12 (1H, s), 10.58 (1H, s).


610
δ 2.34 (6H, s), 7.33-7.40 (3H, m), 7.45 (2H, s), 7.52-7.56 (1H, m), 7.59-7.65 (1H, m), 7.72-7.77 (1H, m),



8.00 (1H, t, J = 7.8 Hz), 10.12 (1H, s), 10.35 (1H, s).


611
δ 2.34 (6H, s), 7.38 (1H, t, J = 7.6 Hz), 7.45-7.65 (5H, m), 7.78-7.83 (2H, m), 7.87 (1H, d, J = 7.6 Hz),



10.10 (1H, s), 10.39 (1H, s).


612
δ 2.34 (6H, s), 7.35-7.45 (5H, m), 7.55-7.59 (1H, m), 7.77-7.81 (1H, m), 8.07-8.12 (2H, m),



10.09 (1H, s), 10.32 (1H, s).


616
δ 2.34 (6H, s), 7.22-7.27 (1H, m), 7.38 (1H, t, J = 7.8 Hz), 7.46 (2H, s), 7.50-7.55 (3H, m), 7.95 (1H, d, J = 7.8 Hz),



7.99-8.03 (1H, m), 10.12 (1H, s), 10.50 (1H, s).


618
δ 2.34 (6H, s), 7.39 (1H, t, J = 7.7 Hz), 7.45 (2H, s), 7.60 (1H, t, J = 7.7 Hz), 7.83 (1H, t, J = 7.7 Hz),



7.95 (2H, d, J = 8.3 Hz), 8.20 (2H, d, J = 8.3 Hz), 10.12 (1H, s), 10.56 (1H, s).


619
δ 2.34 (6H, s), 7.38 (1H, t, J = 7.4 Hz), 7.45 (2H, s), 7.55-7.60 (3H, m), 7.81 (1H, t, J = 7.4 Hz),



8.14 (2H, d, J = 8.8 Hz), 10.11 (1H, s), 10.40 (1H, s).


620
δ 2.34 (6H, s), 3.01 (6H, s), 6.77 (2H, d, J = 9.0 Hz), 7.33 (1H, t, J = 7.0 Hz), 7.45 (2H, s), 7.52 (1H, t, J = 7.0 Hz),



7.78 (1H, t, J = 7.0 Hz), 7.90 (2H, d, J = 9.0 Hz), 9.86 (1H, s), 10.07 (1H, s).


624
δ 2.34 (6H, s), 7.23-7.28 (2H, m), 7.38 (1H, t, J = 7.8 Hz), 7.45 (2H, s), 7.52-7.64 (2H, m),



8.05-8.10 (1H, m), 10.13 (1H, s), 10.88 (1H, s).


628
δ 2.34 (6H, s), 7.37-7.42 (1H, m), 7.40 (2H, s), 7.55-7.58 (1H, m), 7.95-8.07 (2H, m), 8.21 (1H, dd, J = 8.9,



2.1 Hz), 8.30 (1H, dd, J = 8.9, 2.1 Hz), 10.13 (1H, s), 10.75 (1H, s).


629
δ 2.34 (6H, s), 7.39 (1H, t, J = 7.4 Hz), 7.45 (2H, s), 7.52 (1H, 7.4), 7.81 (1H, dd, J = 8.3, 2.7 Hz),



7.88 (1H, dd, J = 8.3, 5.6 Hz), 8.10-8.16 (2H, m), 10.13 (1H, s), 10.75 (1H, s).


630
δ 2.33 (6H, s), 7.34-7.38 (2H, m), 7.43 (2H, s), 7.51-7.54 (1H, m), 7.58-7.60 (1H, m), 7.67-7.71 (1H,



m), 8.00-8.04 (1H, m), 10.10 (1H, s), 10.54 (1H, s).


631
δ 2.34 (6H, s), 7.37 (1H, t, J = 7.9 Hz), 7.45-7.47 (3H, m), 7.52-7.56 (1H, m), 7.65 (1H, dd, J = 10.2,



2.0 Hz), 7.77 (1H, t, J = 7.9 Hz), 7.99-8.02 (1H, m), 10.11 (1H, s), 10.41 (1H, s).


633
δ 2.34 (6H, s), 7.40 (1H, t, J = 8.1 Hz), 7.45 (2H, s), 7.55 (1H, t, J = 6.5 Hz), 7.92 (1H, d, J = 8.1 Hz),



8.10 (1H, t, J = 6.5 Hz), 8.32 (1H, t, J = 8.1 Hz), 8.43 (1H, s), 10.13 (1H, s), 10.84 (1H, s).


634
δ 2.34 (6H, s), 7.39 (1H, t, J = 8.0 Hz), 7.45 (2H, s), 7.51-7.55 (1H, m), 7.83 (1H, d, J = 8.0 Hz),



7.99 (1H, dd, J = 7.7, 2.2 Hz), 8.12 (1H, t, J = 7.7 Hz), 8.30 (1H, d, J = 2.2 Hz), 10.13 (1H, s), 10.78 (1H, s).


638
δ 2.33 (6H, s), 7.37 (1H, t, J = 8.1 Hz), 7.44 (2H, s), 7.50-7.55 (2H, m), 8.03-8.07 (1H, m),



8.26-8.31 (1H, m), 8.41-8.42 (1H, m), 10.10 (1H, s), 10.54 (1H, s).


639
(CDCl3) δ 2.38 (6H, s), 7.38 (2H, s), 7.41-7.49 (2H, m), 7.80 (1H, broad-d, J = 11.4 Hz),



7.90-7.94 (1H, m), 8.32-8.35 (1H, m), 8.57-8.59 (1H, m), 8.62-8.65 (1H, m), 8.74 (1H, s).


648
δ 1.80-1.86 (2H, m), 2.05 (3H, s), 2.33-2.38 (8H, m), 3.99 (2H, t, J = 5.1 Hz), 7.29 (1H, t, J = 7.4 Hz),



7.44-7.48 (3H, m), 7.79 (1H, d, J = 7.4 Hz), 9.25 (1H, s), 10.04 (1H, s).


649
δ 2.29 (6H, s), 7.45 (2H, s), 7.54-7.66 (3H, m), 7.77 (1H, d, J = 8.8 Hz), 7.94 (1H, dd,



J = 2.0, 8.1 Hz), 8.00-8.03 (2H, m), 8.19 (1H, d, J = 2.0 Hz), 10.10 (1H, s), 10.29 (1H, s).


650
δ 2.29 (6H, s), 7.45 (2H, s), 7.48-7.65 (4H, m), 7.93-8.02 (3H, m), 8.23 (1H, dd, J = 2.4,



7.3 Hz), 10.03 (1H, s), 10.32 (1H, s).


651
δ 2.29 (6H, s), 7.45 (2H, s), 7.54 (1H, dd, J = 8.8, 9.8 Hz), 7.96-8.01 (1H, m), 8.23 (2H, d, J = 8.8 Hz),



8.26 (1H, dd, J = 2.4, 8.8 Hz), 8.40 (2H, d, J = 8.8 Hz), 10.05 (1H, s), 10.70 (1H, s).


652
δ 2.29 (6H, s), 7.45 (2H, s), 7.51-7.56 (1H, m), 7.96-8.00 (1H, m), 8.06 (2H, d, J = 8.3 Hz), 8.15 (2H, d, J = 8.3 Hz),



8.25 (1H, dd, J = 2.0, 7.3 Hz), 10.05 (1H, s), 10.61 (1H, s).


653
δ 2.29 (6H, s), 7.33-7.40 (2H, m), 7.45 (2H, s), 7.49-7.54 (1H, m), 7.59-7.65 (1H, m), 7.73-7.77 (1H, m),



7.91-7.95 (1H, m), 8.42 (1H, d, J = 6.3 Hz), 10.05 (1H, s), 10.35 (1H, s).


654
δ 2.29 (6H, s), 7.37-7.45 (4H, m), 7.51 (1H, dd, J = 8.8, 9.8 Hz), 7.93-7.98 (1H, m), 8.06-8.10 (2H, m),



8.22 (1H, dd, J = 2.0, 7.3 Hz), 10.03 (1H, s), 10.37 (1H, s).


655
δ 2.29 (6H, s), 7.45 (2H, s), 7.51-7.56 (1H, m), 7.94-8.00 (3H, m), 8.20 (2H, d, J = 8.3 Hz), 8.25 (1H, dd,



J = 2.0, 7.3 Hz), 10.05 (1H, s), 10.59 (1H, s).


656
δ 2.29 (6H, s), 7.23-7.28 (1H, m), 7.42-7.54 (4H, m), 7.80-7.87 (1H, m), 7.91-7.95 (1H, m), 8.41 (1H, d,



J = 5.9 Hz), 10.05 (1H, s), 10.36 (1H, s).


657
δ 2.30 (6H, s), 7.46 (2H, s), 7.50-7.59 (2H, m), 7.92-7.96 (1H, m), 8.10 (1H, dd, J = 2.0, 7.3 Hz),



8.52-8.56 (2H, m), 10.07 (1H, s), 10.73 (1H, s).


658
δ 2.31 (6H, s), 7.47 (2H, s), 7.55-7.59 (2H, m), 7.62-7.66 (1H, m), 8.01-8.04 (2H, m),



8.09 (1H, s), 8.54 (1H, s), 8.66 (1H, s), 10.27 (1H, s), 10.79 (1H, s).


659
δ 2.34 (6H, s), 7.40 (1H, t, J = 9.3 Hz), 7.45 (2H, s), 7.53-7.64 (3H, m), 7.97-8.05 (3H, m),



8.14 (1H, dd, J = 2.9, 6.3 Hz), 10.03 (1H, s), 10.48 (1H, s).


660
δ 2.40 (6H, s), 7.45 (2H, s), 7.54-7.65 (4H, m), 7.97-8.03 (3H, m), 8.09 (1H, d, J = 2.4 Hz),



10.20 (1H, s), 10.56 (1H, s).


661
δ 2.41 (6H, s), 7.45 (2H, s), 7.54-7.65 (3H, m), 7.72 (1H, d, J = 8.8 Hz), 7.94-7.99 (3H, m), 8.08 (1H, d, J = 2.9 Hz),



10.20 (1H, s), 10.56 (1H, s).


662
δ 2.44 (6H, s), 7.45 (2H, s), 7.53-7.65 (3H, m), 7.79 (1H, dd, J = 2.4, 8.3 Hz),



7.90-7.98 (3H, m), 8.05 (1H, d, J = 2.4 Hz), 10.15 (1H, s), 10.53 (1H, s).


663
δ 2.35 (6H, s), 7.32 (1H, t, J = 8.3), 7.46 (2H, s), 7.54-7.77 (4H, m), 8.00 (2H, dd, J = 1.5, J = 8.3),



10.3 (1H, s), 10.6 (1H, s).


664
(CDCl3) δ 2.53 (6H, s), 7.35 (2H, s), 7.52-7.63 (5H, m), 7.92 (2H, d, J = 8.8 Hz), 8.46 (1H, d, J = 8.8 Hz),



8.57 (1H, s).


665
δ 2.34 (6H, s), 7.37 (1H, t, J = 7.8 Hz), 7.44 (2H, s), 7.53-7.65 (4H, m), 7.77-7.81 (1H, m),



7.99-8.02 (2H, m), 10.09 (1H, broad), 10.29 (1H, broad).


668
δ 2.34 (6H, s), 7.33-7.40 (3H, m), 7.44 (2H, s), 7.51-7.56 (1H, m), 7.58-7.65 (1H, m),



7.72-7.77 (1H, m), 8.00 (1H, t, J = 8.3 Hz), 10.10 (1H, s), 10.34 (1H, s).


670
δ 2.28 (6H, s), 7.31-7.44 (5H, m), 7.57 (1H, t, J = 6.3 Hz), 7.79 (1H, t, J = 7.3 Hz), 8.07-8.09 (2H, m),



10.09 (1H, s), 10.32 (1H, s).


676
δ 7.34 (6H, s), 7.39 (1H, t, J = 7.2 Hz), 7.44 (2H, s), 7.59 (1H, t, J = 7.2 Hz), 7.83 (1H, t, J = 7.2 Hz),



7.99 (2H, d, J = 8.8 Hz), 8.15 (2H, d, J = 8.8 Hz), 10.1 (1H, s), 10.57 (1H, s).


679
δ 2.35 (6H, s), 7.4 (1H, t, J = 7.3 Hz), 7.44 (2H, s), 7.61 (1H, t, J = 7.3 Hz), 7.84 (1H, t, J = 7.3 Hz),



8.24 (2H, d, J = 8.8 Hz), 8.41 (2H, d, J = 8.8 Hz), 10.11 (1H, s), 10.66 (1H, s).


682
δ 2.35 (6H, s), 7.38 (1H, t, J = 8.1 Hz), 7.44 (2H, s), 7.49 (1H, d, J = 8.1 Hz), 7.56 (1H, d, J = 8.1 Hz),



8.07 (2H, d, J = 8.8 Hz), 8.14 (2H, d, J = 8.8 Hz), 10.1 (1H, s), 10.43 (1H, s).


686
δ 2.34 (6H, s), 7.23-7.28 (2H, m), 7.38 (1H, t, J = 7.8 Hz), 7.44 (2H, s), 7.52-7.65 (2H, m),



8.05-8.10 (1H, m), 10.12 (1H, s), 10.88 (1H, s).


699
δ 2.34 (6H, s), 3.39 (3H, s), 7.39 (1H, t, J = 7.8 Hz), 7.44 (2H, s), 7.49-7.59 (2H, m), 8.08-8.13 (2H, m),



8.55 (1H, dd, J = 4.9, 2.0 Hz), 10.12 (1H, s), 10.73 (1H, s).


708
(CDCl3) δ 7.39 (1H, t, J = 7.8 Hz), 7.48-7.64 (3H, m), 7.88-7.96 (4H, m), 8.09-8.13 (2H, m), 8.69 (1H, t,



J = 7.8 Hz), 8.75 (1H, d, J = 7.8 Hz).


711
(CDCl3) δ 7.22 (1H, d, J = 8.3 Hz), 7.35-7.40 (2H, m), 7.56-7.62 (1H, m), 7.91 (1H, t, J = 7.3 Hz),



7.96 (2H, s), 8.15 (1H, d, J = 13.3 Hz), 8.22 (1H, dt, J = 1.9, 8.3 Hz), 8.73 (1H, dt, J = 1.5, 8.3 Hz),



8.92 (1H, d, J = 17.1 Hz).


719
(CDCl3) δ 7.41 (1H, t, J = 8.3 Hz), 7.85 (2H, d, J = 8.3 Hz), 7.92 (1H, d, J = 6.9 Hz), 7.96 (2H, s),



8.03 (2H, d, J = 8.3 Hz), 8.06 (1H, s), 8.10 (1H, s), 8.63 (1H, dt, J = 1.5, 8.3 Hz).


722
(CDCl3) δ 7.42 (1H, t, J = 8.3 Hz), 7.93 (1H, d, J = 5.3 Hz), 7.96 (2H, s), 8.06 (1H, d, J = 12.2 Hz),



8.10 (2H, d, J = 8.8 Hz), 8.13 (1H, s), 8.40 (2H, d, J = 8.8 Hz), 8.64 (1H, dt, J = 1.5, 8.3 Hz).


791
(CDCl3) δ 2.34 (6H, s), 7.37 (1H, t, J = 7.8 Hz), 7.45 (2H, s), 7.54 (2H, t, J = 7.8 Hz), 7.61 (1H, d, J = 7.8 Hz),



7.80 (1H, d, J = 11.7 Hz), 7.82-7.87 (1H, m), 7.92 (2H, d, J = 7.8 Hz), 8.12 (1H, s), 8.62 (1H, dt, J = 2.0,



7.8 Hz).


831
(CDCl3) δ 7.46-7.64 (6H, m), 7.93-7.96 (4H, m), 8.61 (1H, s), 7.75 (1H, dd, J = 1.9, 8.3 Hz).


832
(CDCl3) δ 7.24 (1H, d, J = 8.3 Hz), 7.36 (1H, t, J = 8.3 Hz), 7.47 (1H, t, J = 8.3 Hz), 7.55-7.62 (3H, m),



7.96 (2H, s), 8.21 (1H, dt, J = 2.0, 8.3 Hz), 8.77 (1H, dd, J = 2.0, 8.3 Hz), 9.33 (1H, d, J = 16.6 Hz).


833
(CDCl3) δ 7.45-7.52 (3H, m), 7.60 (1H, d, J = 8.8 Hz), 7.96 (2H, s), 8.29 (1H, d, J = 7.8 Hz), 8.57 (1H,



dd, J = 2.0, 4.4 Hz), 8.72 (1H, d, J = 7.8 Hz), 9.00 (1H, s).


1001
δ 2.20 (6H, s), 3.45 (3H, s), 7.23-7.30 (5H, m), 7.43-7.45 (4H, m), 7.73-7.76 (2H, m), 9.88 (1H, s).


1013
δ 2.20 (6H, s), 3.48 (3H, s), 7.39-7.97 (8H, m), 7.43 (2H, s), 9.90 (1H, s).


1016
δ 2.21 (6H, s), 3.46 (3H, s), 7.40-8.03 (10H, m), 9.91 (1H, s).


1032
δ 2.08 (3H, s), 2.30 (6H, s), 7.45 (2H, s), 7.47 (1H, d, J = 7.8 Hz), 7.54 (1H, t, J = 7.8 Hz), 7.66 (1H, d, J = 7.8 Hz),



7.75 (1H, d, J = 7.8 Hz), 7.82 (1H, d, J = 7.8 Hz), 8.04 (1H, dd, J = 2.0, 7.8 Hz), 8.13 (1H, s),



8.35 (1H, s), 9.99 (1H, s), 10.16 (1H, s), 10.48 (1H, s).


1043
(CDCl3) δ 1.38 (6H, m), 2.37 (6H, s), 3.13 (1H, broad), 3.33 (3H, broad), 3.78 (1H, broad), 3.89 (1H,



broad), 7.37 (2H, s), 7.48 (1H, d, J = 7.8 Hz), 7.58 (1H, t, J = 7.8 Hz), 7.77 (1H, s), 7.90 (1H, s), 7.93 (1H,



broad).


1089
(CDCl3) δ 0.89 (3H, t, J = 7.3 Hz), 1.53-1.62 (2H, m), 2.61 (2H, t, J = 7.3 Hz), 3.50 (3H, broad), 6.80 (1H,



broad), 7.03 (1H, broad), 7.22 (1H, broad), 7.34 (3H, broad), 7.47 (1H, s), 7.67-7.76 (3H, broad-m),



7.93 (1H, s).


1091
(CDCl3) δ 0.88 (3H, t, J = 7.3 Hz), 1.53-1.63 (2H, m), 2.62 (2H, t, J = 7.8 Hz), 3.52 (3H, s),



6.83-6.89 (2H, m), 7.26-7.32 (3H, m), 7.41 (1H, t, J = 7.8 Hz), 7.48 (1H, s), 7.66 (1H, s), 7.76 (2H, d, J = 8.8 Hz),



7.93 (1H, d, J = 1.5 Hz).


1097
(CDCl3) δ 0.90 (3H, t, J = 7.3 Hz), 1.55-1.65 (2H, m), 2.64 (2H, t, J = 7.8 Hz), 3.55 (3H, s), 7.27 (1H, s),



7.40-7.44 (3H, m), 7.49-7.51 (3H, m), 7.59 (1H, s), 7.69 (1H, s), 7.76 (1H, d, J = 7.8 Hz), 7.95 (1H, s).


1100
(CDCl3) δ 0.88 (3H, t, J = 7.3 Hz), 1.54-1.64 (2H, m), 2.63 (2H, t, J = 7.8 Hz), 3.56 (3H, s), 7.29 (1H, s),



7.40-7.50 (4H, m), 7.59 (1H, s), 7.71 (1H, s), 7.76 (1H, d, J = 7.3 Hz), 7.94 (1H, d, J = 1.5 Hz), 8.06 (2H, d,



J = 8.8 Hz).


1125
(CDCl3) δ 2.25 (6H, s), 3.54 (3H, s), 6.84 (1H, broad-s), 7.00-7.10 (2H, m), 7.20-7.40 (6H, m),



7.50-7.60 (1H, broad), 7.60-7.70 (1H, broad).


1126
(CDCl3) δ 3.57 (3H, s), 7.20-7.24 (2H, m), 7.29-7.32 (3H, m), 7.34 (1H, t, J = 7.8 Hz), 7.40-7.44 (2H, m),



7.57 (1H, d, J = 7.8 Hz), 7.86-7.91 (1H, m), 7.92 (2H, s).


1206
δ 1.17 (3H, broad), 2.22 (6H, s), 3.94 (2H, broad), 7.01-7.08 (2H, m), 7.29-7.43 (6H, m),



7.72-7.77 (2H, m), 9.90 (1H, s).


1207
δ 1.26 (3H, t, J = 6.8 Hz), 2.04 (6H, s), 4.11 (2H, q, J = 6.8 Hz), 7.16-7.70 (12H, m).


1208
δ 2.28 (6H, s), 3.36 (3H, s), 7.27-7.32 (6H, m), 7.43 (2H, s), 7.55-7.57 (2H, broad), 9.96 (1H, s).


1209
δ 2.28 (6H, s), 3.47 (3H, s), 6.98 (1H, broad), 7.11 (2H, broad), 7.19 (1H, broad), 7.37 (1H, broad),



7.44 (2H, s), 7.51 (1H, broad), 7.74 (1H, broad), 9.94 (1H, s).


1210
δ 2.23 (3H, s), 2.29 (6H, s), 7.07-7.26 (5H, m), 7.44 (2H, s), 7.56-7.77 (2H, m), 9.98 (1H, s).


1211
δ 2.24 (3H, s), 2.28 (6H, s), 7.08-7.09 (2H, m), 7.22-7.28 (2H, m), 7.44 (2H, s), 7.51-7.58 (3H, m),



9.99 (1H, s).


1212
δ 2.29 (6H, s), 3.12 (3H, s), 7.17-8.02 (9H, m), 9.95 (1H, s).


1213
δ 2.26 (6H, s), 3.41 (3H, s), 7.12-8.34 (9H, m), 9.92 (1H, s).


1214
δ 2.26 (6H, s), 3.40 (3H, s), 7.29 (1H, broad), 7.44 (2H, s), 7.59-7.81 (4H, m), 8.12 (2H, broad),



9.91 (1H, s).


1215
δ 2.26 (6H, s), 3.40 (3H, s), 7.31-7.39 (7H, m), 7.50-7.56 (1H, m), 7.81-7.83 (1H, m), 9.94 (1H, s).


1216
δ 2.27 (6H, s), 3.39 (3H, s), 7.31 (1H, m), 7.47 (2H, s), 7.60-7.67 (3H, m), 7.72-7.80 (3H, m),



9.96 (1H, s).


1217
δ 2.27 (6H, s), 3.37 (3H, s), 7.29 (2H, broad), 7.44-7.48 (3H, m), 7.59-7.64 (2H, m), 7.76 (2H, broad),



9.94 (1H, s).


1218
δ 2.27 (6H, s), 3.39 (3H, s), 7.03-7.72 (9H, m), 9.94 (1H, s).


1219
δ 2.28 (6H, s), 3.36 (3H, s), 7.18-8.04 (9H, m), 9.98 (1H, m).


1220
δ 2.28 (6H, s), 3.34 (3H, s), 7.12-7.56 (9H, m), 9.97 (1H, s).


1229
δ 2.28 (6H, s), 3.39 (3H, s), 7.02-7.28 (2H, m), 7.35-7.43 (2H, m), 7.55-7.70 (2H, m), 7.93-7.99 (2H,



m), 9.95 (1H, m).


1235
δ 2.26 (6H, s), 3.43 (3H, s), 7.27 (1H, t, J = 7.8 Hz), 7.44 (2H, s), 7.58-7.65 (2H, m), 7.71 (1H, t, J = 7.8),



8.00 (1H, dd, J = 8.3, 2.0 Hz), 8.04 (1H, dd, J = 9.3, 2.0 Hz), 9.91 (1H, s).


1236
δ 2.29 (6H, s), 3.41 (3H, s), 7.44-7.46 (3H, m), 7.59-7.61 (2H, m), 7.72-7.77 (1H, m), 7.88 (1H, d, J = 6.8 Hz),



7.95-7.99 (1H, m), 9.95 (1H, s).


1237
δ 2.29 (6H, s), 3.40 (3H, s), 7.08-7.91 (8H, m), 9.94 (1H, s).


1238
δ 2.28 (6H, s), 3.39 (3H, s), 7.21-7.28 (1H, m), 7.34-7.44 (3H, m), 7.54-7.60 (2H, m), 7.79-7.91 (2H,



m), 9.95 (1H, m).


1245
δ 2.28 (6H, s), 3.41 (3H, s), 7.25 (1H, t, J = 7.6 Hz), 7.36 (1H, d, J = 4.7 Hz), 7.44 (2H, s),



7.57-7.64 (2H, m), 7.92 (1H, d, J = 7.6 Hz), 8.32 (1H, dd, J = 4.7, 1.9 Hz), 9.97 (1H, s).


1246
δ 2.31 (6H, s), 3.60 (3H, s), 7.25-7.31 (2H, m), 7.44 (2H, s), 7.57-7.59 (2H, m), 7.97-8.01 (1H, m),



8.17-8.18 (1H, m), 9.97 (1H, s).


1247
δ 2.28 (6H, s), 3.39 (3H, s), 7.33 (1H, d, J = 7.6 Hz), 7.44 (2H, s), 7.61-7.69 (3H, m), 7.80 (1H, broad),



8.30 (1H, broad), 10.01 (1H, s).


1255
δ 2.29 (6H, s), 3.35 (3H, s), 7.19-7.70 (10H, m), 9.98 (1H, s).


1256
δ 2.28 (6H, s), 2.30 (3H, s), 3.32 (3H, s), 6.98-7.72 (9H, m), 9.93 (1H, s).


1257
δ 2.23 (3H, s), 2.29 (6H, s), 3.34 (3H, s), 7.07-7.38 (5H, m), 7.53-7.76 (2H, m), 7.43 (2H, s), 9.98 (1H,



s).


1258
δ 2.27 (6H, s), 2.33 (3H, s), 3.31 (3H, s), 6.98-7.51 (9H, s), 9.93 (1H, s).


1259
δ 2.29 (6H, s), 3.41 (3H, s), 7.18 (1H, J = 7.3 Hz), 7.44 (2H, s), 7.46-7.57 (2H, m), 7.67 (1H, t, J = 7.3 Hz),



7.73-7.82 (2H, m), 8.01 (1H, d, J = 7.8 Hz), 9.95 (1H, s).


1260
δ 2.26 (6H, s), 3.36 (3H, s), 7.42 (2H, s), 7.59 (1H, broad), 7.7 (1H, broad), 7.82 (1H, t, J = 7.9 Hz),



8.2 (1H, broad), 8.34-8.37 (1H, m), 8.48 (1H, dd, J = 7.9, 1.7 Hz), 8.62 (1H, t, J = 2.0 Hz), 9.92 (1H, s).


1261
δ 2.27 (6H, s), 3.37 (3H, s), 7.43 (2H, s), 7.59-7.65 (2H, m), 8.11 (1H, broad), 8.18 (2H, d, J = 8.8 Hz),



8.29 (2H, d, J = 8.8 Hz), 9.91 (1H, s).


1262
δ 2.33 (6H, s), 3.35 (3H, s), 7.30-7.83 (9H, m), 9.93 (1H, s).


1263
δ 2.27 (6H, s), 3.37 (3H, s), 7.18-7.80 (9H, m), 9.96 (1H, s).


1264
δ 2.27 (6H, s), 3.35 (3H, s), 7.43 (2H, s), 7.48 (1H, broad), 7.58 (1H, broad), 7.75 (1H, broad),



7.99 (2H, d, J = 8.5 Hz), 8.08 (2H, d, J = 8.5 Hz), 9.95 (1H, s).


1265
δ 2.27 (6H, s), 3.36 (3H, s), 7.03-7.73 (9H, m), 9.93 (1H, s).


1266
δ 2.28 (6H, s), 3.35 (2H, s), 7.18-7.61 (9H, m), 9.99 (1H, s).


1267
δ 2.28 (6H, s), 3.39 (3H, s), 7.11-7.18 (3H, m), 7.26-7.30 (1H, t, J = 7.8 Hz), 7.40-7.47 (3H, m),



7.58 (2H, t, J = 7.6 Hz), 9.96 (1H, s).


1274
δ 2.27 (6H, s), 3.37 (3H, s), 7.29 (3H, broad), 7.41-7.47 (4H, m), 7.59-7.61 (2H, m), 9.95 (1H, s).


1293
δ 2.28 (6H, s), 3.41 (3H, s), 7.25 (1H, t, J = 7.6 Hz), 7.35 (1H, dd, J = 7.3, 4.9 Hz), 7.43 (2H, s),



7.57-7.63 (2H, m), 7.91 (1H, d, J = 7.6 Hz), 8.32 (1H, dd, J = 4.9, 2.0 Hz), 9.96 (1H, s).


1294
δ 2.28 (6H, s), 3.39 (3H, s), 7.31-7.35 (1H, m), 7.42 (2H, s), 7.43-7.48 (1H, m), 7.61-7.75 (2H, m),



7.80 (1H, s), 8.32 (1H, broad), 10.01 (1H, s).


1463
δ 2.25 (6H, s), 3.38 (3H, s), 7.27-7.41 (6H, m), 7.45 (2H, s), 7.90 (1H, broad), 8.05 (1H, d, J = 6.8 Hz),



9.96 (1H, s).


1464
δ 2.23 (6H, s), 3.42 (3H, s), 7.41 (1H, broad), 7.45 (2H, s), 7.60 (2H, broad), 7.90 (1H, broad),



8.08-8.13 (3H, broad), 9.93 (1H, s).


1465
δ 2.25 (6H, s), 3.40 (3H, s), 7.39-7.42 (1H, m), 7.45 (2H, s), 7.50 (1H, broad), 7.78 (1H, broad), 7.91 (1H,



broad), 7.97-8.10 (3H, m), 9.94 (1H, s).


1478
δ 2.29 (6H, s), 3.24 (3H, s), 6.84 (1H, d, J = 7.8 Hz), 7.12 (1H, t, J = 7.8 Hz), 7.33 (2H, s),



7.50-7.64 (4H, m), 7.85-7.88 (2H, m), 7.98-8.03 (1H, m), 10.22 (1H, s).


1479
δ 2.41 (3H, s), 3.25 (3H, s), 6.95 (1H, dd, J = 1.5, 7.8 Hz), 7.16 (1H, t, J = 7.8 Hz),



7.50-7.64 (4H, m), 7.68 (1H, s), 7.86-7.88 (2H, m), 7.93 (1H, t, J = 1.5 Hz), 7.98-8.00 (1H, m),



10.24 (1H, s).


1480
(CDCl3) δ 3.34 (3H, s), 7.13-7.19 (2H, m), 7.49-7.58 (3H, m), 7.70-7.73 (2H, m), 7.78-7.91 (4H, m),



8.12 (1H, s).


1481
(CDCl3) δ 3.35 (3H, s), 7.15-7.20 (3H, m), 7.32 (1H, t, J = 7.8 Hz), 7.51-7.55 (1H, m), 7.71 (1H, d, J = 2.9 Hz),



7.72 (1H, d, J = 2.0 Hz), 7.80 (2H, s), 8.14 (1H, dt, J = 2.0, 7.8 Hz), 8.37 (1H, d, J = 16.1 Hz).


1482
δ 1.18 (3H, t, J = 7.3 Hz), 2.30 (6H, s), 3.76 (2H, q, J = 7.3 Hz), 6.81 (1H, d, J = 7.8 Hz),



7.11 (1H, t, J = 7.8 Hz), 7.33 (2H, s), 7.50-7.62 (4H, m), 7.84-7.88 (2H, m),



7.95-8.00 (1H, m), 10.20 (1H, s).


1483
δ 1.44 (6H, d, J = 6.3 Hz), 2.07 (6H, s), 5.35 (1H, septet, J = 6.3 Hz), 6.84 (1H, d, J = 7.8 Hz),



7.21 (1H, t, J = 7.8 Hz), 7.21 (2H, s), 7.50-7.61 (3H, m), 7.75 (1H, dd, J = 1.5,



7.8 Hz), 7.86-7.89 (3H, m), 10.29 (1H, s).


1484
δ 2.18 (3H, s), 2.32 (6H, s), 7.37-7.59 (11H, m), 10.42 (1H, s).


1485
δ 2.34 (3H, s), 2.35 (6H, s), 7.34-8.02 (10H, m), 10.33 (1H, s).


1486
δ 2.33 (3H, s), 2.36 (6H, s), 7.29-8.12 (9H, m), 10.37 (1H, s).


1487
δ 2.20 (6H, s), 3.08 (3H, s), 3.20 (3H, s), 6.93-7.39 (10H, m), 7.45-7.51 (1H, m).


1607
(CDCl3) δ 3.31 (3H, s), 3.35 (3H, s), 6.81 (1H, dt, J = 6.8, 1.0 Hz), 6.94 (1H, t, J = 7.8 Hz), 7.10-7.24 (5H,



m), 7.35-7.40 (1H, m), 7.41 (1H, s), 7.78 (2H, s).


1617
(CDCl3) δ 3.30 (3H, s), 3.33 (3H, s), 6.76-7.00 (4H, m), 7.19-7.23 (3H, m), 7.37 (1H, s), 7.77 (2H, s).


1645
(CDCl3) δ 3.30 (3H, s), 3.36 (3H, s), 6.96-7.06 (3H, m), 7.12-7.16 (1H, m), 7.39-7.42 (2H, m), 7.95 (2H,



s), 8.24 (1H, s).


1654
(CDCl3) δ 3.30 (3H, s), 3.42 (3H, s), 7.01 (1H, d, J = 7.3 Hz), 7.10 (1H, t, J = 7.8 Hz), 7.16 (1H, dd, J = 1.4,



7.8 Hz), 7.41 (1H, t, J = 1.4 Hz), 7.54 (1H, dd, J = 1.9 Hz), 7.56 (1H, d, J = 1.9 Hz), 7.80 (1H, s),



7.81 (2H, s).


1655
(CDCl3) δ 3.29 (3H, s), 3.38 (3H, s), 3.78 (3H, s), 6.73 (1H, d, J = 8.3 Hz), 6.96 (1H, d, J = 8.3 Hz),



7.04 (1H, t, J = 7.8 Hz), 7.08 (1H, d, J = 1.5 Hz), 7.14 (1H, d, J = 7.8 Hz), 7.40 (1H, s), 7.54 (1H, d, J = 8.3 Hz),



7.81 (2H, s).


1697
δ 2.23 (6H, s), 3.32 (3H, s), 3.39 (3H, s), 7.15-7.43 (10H, m).


2001
(CDCl3) δ 2.36 (6H, s), 7.36 (2H, s), 7.53-7.57 (2H, m), 7.61-7.65 (1H, m), 7.95-8.03 (3H, m),



8.08 (1H, dd, J = 7.3, 1.0 Hz), 8.52 (1H, broad-s), 8.62 (1H, dd, J = 8.3, 1.0 Hz), 9.19 (1H, broad-s).


2004
δ 2.30 (6H, s), 7.37-7.43 (2H, m), 7.46 (2H, s), 7.65 (1H, d, J = 8.1 Hz), 7.83 (1H, dd, J = 7.5, 5.6 Hz),



7.88 (1H, d, J = 7.5 Hz), 8.13 (1H, t, J = 8.1 Hz), 8.40 (1H, d, J = 8.1 Hz), 10.08 (1H, s), 10.62 (1H, s).


2032
δ 2.30 (6H, s), 7.46 (2H, s), 7.75-7.78 (1H, m), 7.91 (1H, dd, J = 7.3, 1.0 Hz), 8.13-8.18 (2H, m),



8.27 (1H, d, J = 8.0 Hz), 8.56 (1H, d, J = 8.0 Hz), 8.77 (1H, d, J = 1.0 Hz), 10.62 (1H, s), 10.75 (1H, s).


2033
δ 2.27 (6H, s), 6.16 (2H, s), 6.71 (1H, d, J = 7.6 Hz), 7.01 (2H, d, J = 1.0 Hz), 7.24 (1H, d, J = 6.9 Hz),



7.42 (2H, s), 7.59 (1H, dd, J = 7.6, 6.9 Hz), 7.65 (1H, s), 9.94 (1H, s).


2034
δ 2.32 (6H, s), 7.47 (2H, s), 7.90-7.93 (3H, m), 8.15 (1H, t, J = 8.0 Hz), 8.37 (1H, d, J = 8.0 Hz),



8.83 (2H, dd, J = 4.6, 1.7 Hz), 10.12 (1H, s), 10.92 (1H, s).


2035
δ 2.30 (6H, s), 7.46 (2H, s), 7.55-7.56 (1H, m), 7.89 (1H, d, J = 7.4 Hz), 8.14 (1H, t, J = 7.8 Hz),



8.34-8.41 (2H, m), 8.45 (1H, dd, J = 5.4, 1.2 Hz), 10.03 (1H, s), 10.90 (1H, s).


2036
δ 2.29 (6H, s), 7.45 (2H, s), 7.59 (1H, t, J = 6.3 Hz), 7.88 (1H, d, J = 6.3 Hz), 8.12-8.16 (2H, m),



8.39 (1H, m), 8.55 (1H, m), 9.93 (1H, s), 11.25 (1H, s).


2037
δ 2.32 (6H, s), 7.47 (2H, s), 7.67 (1H, d, J = 7.6 Hz), 7.75 (1H, d, J = 8.3 Hz), 7.90 (1H, d, J = 7.6 Hz),



8.14 (1H, t, J = 7.6 Hz), 8.29 (1H, dd, J = 8.3 Hz, 2.0 Hz), 8.89 (1H, d, J = 2.0 Hz), 10.07 (1H, s),



10.97 (1H, s).


2082
δ 2.20 (6H, s), 3.58 (3H, s), 7.29-7.39 (5H, m), 7.43 (2H, s), 7.50 (1H, d, J = 7.4 Hz), 7.83 (1H, t, J = 7.4 Hz),



7.94 (1H, t, J = 7.4 Hz), 9.91 (1H, s).


2085
δ 2.22 (6H, s), 3.57 (3H, s), 7.12 (1H, t, J = 9.2 Hz), 7.20 (1H, t, J = 7.3 Hz), 7.28-7.30 (1H, m),



7.44 (2H, s), 7.55 (1H, t, J = 7.2 Hz), 7.63 (1H, broad), 7.87 (1H, d, J = 7.2 Hz), 7.98 (1H, t, J = 7.2 Hz),



9.90 (1H, s).


2093
δ 2.14 (6H, s), 3.57 (3H, s), 7.42 (2H, s), 7.66-7.87 (3H, m), 7.96-8.09 (4H, m), 9.77 (1H, s).


2116
δ 2.23 (6H, s), 3.55 (3H, s), 7.45 (3H, s), 7.89-9.91 (2H, m), 8.03-8.10 (3H, m), 9.82 (1H, s).


2117
δ 2.13 (6H, s), 3.58 (3H, s), 7.42 (2H, s), 7.46 (1H, d, J = 8.2 Hz), 7.72-7.75 (2H, m), 7.90 (1H, d, J = 8.2 Hz),



8.08 (1H, t, J = 8.2 Hz), 8.35 (1H, d, J = 2.0 Hz), 9.83 (1H, s).


2162
(CDCl3) δ 2.38 (6H, s), 7.38 (2H, s), 7.53-7.57 (2H, m), 7.62 (1H, d, J = 7.8 Hz), 7.68 (1H, dd, J = 4.9,



1.5 Hz), 7.85 (1H, broad-s), 7.95 (2H, d, J = 7.8 Hz), 8.52 (1H, d, J = 4.9 Hz), 8.22 (1H, broad-s),



8.88 (1H, s).


2163
(CDCl3) δ 2.36 (6H, s), 7.38 (2H, s), 7.55-7.59 (2H, m), 7.64-7.72 (2H, m), 7.75 (1H, broad-s),



8.01 (2H, d, J = 7.3 Hz), 8.41 (1H, d, J = 6.8 Hz), 9.14 (1H, d, J = 2.4 Hz), 10.9 (1H, broad-s).


2164
(CDCl3) δ 2.34 (6H, s), 7.47 (2H, s), 7.62-7.65 (2H, m), 7.70-7.81 (2H, m), 8.04-8.04 (3H, m),



8.64 (1H, dd, J = 8.3, 1.5 Hz), 10.9 (1H, broad-s), 12.3 (1H, broad-s).


2165
δ 2.35 (6H, s), 7.29-8.03 (10H, m), 8.75 (1H, d, J = 2.0 Hz).


2168
δ 2.25 (6H, s), 3.32 (3H, s), 7.26 (1H, d, J = 7.7 Hz), 7.38 (1H, d, J = 7.7 Hz), 7.44 (2H, s), 7.55 (1H, t, J = 7.7 Hz),



7.90 (3H, m), 8.11 (2H, m), 12.40 (1H, s).


2201
(CDCl3) δ 2.38 (6H, s), 7.25-8.00 (11H, m), 8.34 (1H, s), 8.85 (1H, broad.).


2202
(CDCl3) δ 2.36 (6H, s), 7.37 (2H, s), 7.47-7.61 (5H, m), 7.85-8.03 (4H, m),



8.57 (1H, s), 9.18 (1H, s).


2203
(CDCl3) δ 2.38 (6H, s), 7.41 (2H, s), 7.45-7.55 (4H, m), 7.90-7.96 (4H, m),



8.57 (1H, broad), 8.74 (1H, broad), 9.18 (1H, broad).





Comp. No.

1H-NMR (CDCl3, ppm)






I-1 
δ 2.34 (6H, s), 3.87 (2H, broad-s), 6.86-6.89 (1H, m), 7.21-7.30 (3H, m), 7.33 (2H, s), 7.39 (1H, s)


I-2 
δ 2.34 (6H, s), 3.87 (2H, broad), 6.86-6.89 (1H, m), 7.20-7.35 (6H, m)


I-4 
δ 2.60 (3H, s), 3.92 (2H, broad-s), 6.89-6.92 (1H, m), 7.24-7.32 (3H, m), 7.46 (1H, s), 7.76 (1H,



broad-s)


I-5 
δ 2.27 (6H, s), 3.31 (3H, s), 6.40-6.43 (1H, m), 6.54-6.58 (1H, m), 6.71 (1H, t, J = 2.0 Hz), 6.76-6.86 (1H,



m), 7.22 (2H, s)


I-6 
δ 1.45 (6H, d, J = 6.3 Hz), 2.07 (6H, s), 3.53 (2H, broad), 5.37 (1H, septet, J = 6.3 Hz), 6.56-6.63 (3H, m),



6.96 (1H, t, J = 7.8 Hz), 7.16 (2H, s)


I-7 
δ 1.17 (3H, t, J = 7.6 Hz), 2.28 (3H, s), 2.65 (2H, q, J = 7.6 Hz), 3.85 (2H, broad-s), 6.82-6.85 (1H, m),



7.21-7.23 (3H, m), 7.34 (2H, s), 7.64 (1H, s)


I-8 
δ 1.22 (6H, t, J = 7.6 Hz), 2.69 (4H, q, J = 7.6 Hz), 3.86 (2H, broad-s), 6.86-6.89 (1H, m), 7.15-7.36 (4H,



m), 7.38 (2H, s)


I-9 
δ 1.23 (3H, t, J = 7.3 Hz), 2.76 (2H, q, J = 7.3 Hz), 3.88 (2H, broad-s), 6.88-6.91 (1H, m), 7.26-7.32 (3H,



m), 7.50 (1H, s), 7.53 (1H, s), 7.95 (1H, d, J = 1.5 Hz)


I-10
δ 1.22 (6H, d, J = 6.8 Hz), 2.32 (3H, s), 3.17 (1H, septet, J = 6.8 Hz), 3.87 (2H, broad-s), 6.85-6.93 (1H,



m), 7.20-7.29 (3H, m), 7.35 (1H, s), 7.40-7.45 (2H, m).


I-11
δ 2.35 (3H, s), 3.85 (5H, s), 6.85-6.89 (1H, m), 6.95 (1H, s), 7.13 (1H, s), 7.23-7.30 (3H, m), 7.62 (1H, s)


I-12
δ 1.25 (3H, t, J = 7.6 Hz), 2.76 (2H, q, J = 7.6 Hz), 3.88 (2H, broad-s), 6.87-6.91 (1H, m), 7.24-7.31 (3H,



m), 7.47 (1H, s), 7.55 (1H, s), 7.57 (1H, s)


I-13
δ 2.35 (3H, s), 2.57 (3H, d, J = 6.8 Hz), 3.88 (2H, broad-s), 6.88-6.91 (1H, m), 7.25-7.34 (4H, m),



7.67 (1H, s)


I-14
δ 2.41 (3H, s), 3.88 (2H, broad-s), 6.87-6.91 (1H, m), 7.25-7.31 (3H, m), 7.47 (1H, s), 7.65 (1H, s),



7.72 (1H, s)


I-15
δ 1.23 (3H, t, J = 7.3 Hz), 2.74 (2H, q, J = 7.3 Hz), 3.87 (2H, broad-s), 6.86-6.91 (1H, m), 7.25-7.31 (3H,



m), 7.50 (1H, s), 7.59 (1H, s), 7.73 (1H, d, J = 1.5 Hz)


I-16
(DMSO-d6) δ 0.84 (3H, t, J = 7.3 Hz), 1.48-1.58 (2H, m), 2.66 (2H, t, J = 7.3 Hz), 5.36 (2H, broad-s),



6.77 (1H, dd, J = 1.0 Hz, 7.8 Hz), 7.10-7.19 (3H, m), 7.59 (1H, s), 7.80 (1H, s), 10.03 (1H, s)


I-17
δ 0.90 (3H, t, J = 7.3 Hz), 1.25-1.37 (2H, m), 1.55-1.63 (2H, m), 2.72 (2H, t, J = 7.8 Hz), 3.89 (2H, broad),



6.87-6.91 (1H, m), 7.24-7.31 (3H, m), 7.48 (1H, s), 7.55 (1H, s), 7.73 (1H, d, J = 1.5 Hz)


I-18
δ 2.39 (3H, s), 2.66 (3H, d, J = 6.9 Hz), 7.43 (1H, s), 7.75-7.79 (2H, m), 8.33 (1H, d, J = 8.3 Hz),



8.48 (1H, d, J = 8.3 Hz), 8.80 (1H, s)


I-19
δ 2.41 (3H, s), 3.88 (2H, s), 6.86-6.91 (1H, m), 7.28-7.32 (3H, m), 7.49 (1H, s), 7.58 (1H, s), 7.93 (1H, d,



J = 1.2 Hz)


I-20
δ 0.91 (3H, t, J = 7.3 Hz), 1.58-1.67 (2H, m), 2.69 (2H, t, J = 7.8 Hz), 3.88 (2H, broad-s), 6.87-6.90 (1H,



m), 7.26-7.31 (3H, m), 7.50 (1H, s), 7.54 (1H, s), 7.95 (1H, d, J = 2.0 Hz)


I-21
δ 2.33 (6H, s), 3.87 (2H, broad-s), 6.86-6.89 (1H, m), 7.21-7.29 (3H, m), 7.34 (2H, s), 7.52 (1H, s)


I-22
δ 2.32 (6H, s), 3.86 (2H, broad-s), 6.85-6.88 (1H, m), 7.20-7.28 (3H, m), 7.33 (2H, s), 7.60 (1H, s)


I-23
δ 3.99 (2H, broad-s), 6.85-6.88 (1H, m), 7.23-7.34 (3H, m), 7.91 (2H, s), 8.69 (1H, s)


I-24
(DMSO-d6) δ 5.39 (2H, broad-s), 6.77-6.80 (1H, m), 7.12-7.19 (3H, m), 8.49 (2H, s), 10.53 (1H, s)


I-26
δ 3.88 (2H, s), 6.90 (1H, d, J = 6.8 Hz), 7.23-7.32 (3H, m), 7.60 (1H, s), 7.92 (2H, s)


I-27
δ 3.89 (2H, broad-s), 6.90 (1H, dt, J = 2.5 Hz, 6.3 Hz), 7.25-7.32 (3H, m), 7.59 (1H, s), 7.72 (2H, s)


I-28
δ 3.89 (2H, broad-s), 6.90 (1H, dt, J = 2.5 Hz, 6.4 Hz), 7.28-7.30 (3H, m), 7.60 (1H, s), 7.93 (2H, s)


I-29
δ 3.92 (2H, s), 6.92 (1H, dt, J = 1.5 Hz, 7.3 Hz), 7.23-7.30 (3H, m), 7.79 (1H, s), 8.04 (2H, s)


I-30
δ 3.89 (2H, broad-s), 6.90 (1H, dd, J = 2.4 Hz, 4.9 Hz), 7.23-7.32 (3H, m), 7.61 (1H, s), 7.93 (2H, s)


I-31
δ 3.88 (2H, broad-s), 6.90 (1H, d, J = 6.3 Hz), 7.23-7.32 (3H, m), 7.62 (1H, s), 7.92 (2H, s)


I-32
δ 6.90-6.94 (1H, m), 7.28-7.33 (3H, m), 7.73 (1H, s), 8.02 (1H, s), 8.25 (1H, s)


I-33
δ 2.31 (6H, s), 2.90 (3H, s), 6.81 (1H, dd, J = 1.9 Hz, 7.8 Hz), 7.15-7.18 (2H, m), 7.30 (1H, t, J = 7.8 Hz),



7.42 (1H, s), 7.52 (2H, s)


I-35
δ 0.89 (3H, t, J = 7.3 Hz), 1.23-1.37 (2H, m), 1.54-1.62 (2H, m), 2.70 (2H, t, J = 7.8 Hz), 3.88 (2H,



broad), 6.86-6.90 (1H, m), 7.22-7.30 (3H, m), 7.44 (1H, s), 7.56-7.59 (2H, m).


I-36
(DMSO-d6) δ 0.82 (3H, t, J = 7.3 Hz), 1.19-1.29 (2H, m), 1.44-1.52 (2H, m), 2.66 (2H, t, J = 7.8 Hz),



5.36 (2H, broad-s), 6.75-6.81 (1H, m), 7.12-7.19 (3H, m), 7.58 (1H, s), 7.95 (1H, d, J = 1.5 Hz), 10.02 (1H,



s).


I-37
(DMSO-d6) δ 5.37 (2H, s), 6.76-6.80 (1H, m), 7.13-7.19 (3H, m), 8.13 (2H, s), 10.35 (1H, s).


I-38
δ 0.79 (3H, t, J = 7.3 Hz), 1.23 (3H, d, J = 6.8 Hz), 1.53-1.63 (2H, m), 2.90-2.99 (1H, m), 3.87 (2H,



broad-s), 6.85-6.89 (1H, m), 7.25-7.29 (3H, m), 7.44 (1H, s), 7.55-7.57 (2H, m).


I-39
δ 0.79 (3H, t, J = 7.3 Hz), 1.21 (3H, d, J = 6.8 Hz), 1.50-1.61 (2H, m), 2.91-3.00 (1H, m), 3.88 (2H,



broad-s), 6.86-6.91 (1H, m), 7.26-7.31 (3H, m), 7.51 (2H, s), 7.94 (1H, d, J = 2.0 Hz).


I-40
(DMSO-d6) δ 5.39 (2H, broad-s), 6.77-6.80 (1H, m), 7.13-7.20 (3H, m), 8.02 (2H, s), 10.35 (1H, s).


I-41
(DMSO-d6) δ 5.38 (2H, broad-s), 6.75-6.80 (1H, m), 7.12-7.19 (3H, m), 8.01 (2H, s), 10.34 (1H, s).


I-42
(DMSO-d6) δ 3.34 (3H, s), 5.40 (2H, broad-s), 6.80 (1H, d, J = 7.8 Hz), 7.14-7.21 (3H, m), 8.19 (1H, s),



8.45 (1H, s), 10.36 (1H, s).


I-48
(DMSO-d6) δ 2.48 (3H, s), 5.36 (2H, broad-s), 6.77 (1H, d, J = 7.3 Hz), 7.11-7.18 (3H, m), 7.36 (1H, s),



7.70 (1H, s), 10.09 (1H, s).


I-53
δ 0.91 (3H, t, J = 7.3 Hz), 1.57-1.66 (2H, m), 2.69 (2H, t, J = 7.8 Hz), 2.88 (3H, s), 3.97 (1H, s), 6.80 (1H,



dd, J = 2.4, 7.8 Hz), 7.19-7.32 (3H, m), 7.49 (1H, s), 7.60 (1H, s), 7.94 (1H, d, J = 2.0 Hz).


I-55
δ 2.73 (3H, s), 3.32 (3H, s), 6.54 (1H, d, J = 8.3 Hz), 6.73 (1H, s), 6.74 (1H, d, J = 8.3 Hz), 6.96 (1H, t, J = 8.3 Hz),



7.77 (2H, s).


I-56
δ 2.91 (3H, s), 6.82-6.85 (1H, m), 7.21-7.23 (2H, m), 7.32 (1H, t, J = 7.8 Hz), 7.64 (1H, s), 7.93 (2H, s)


I-83
δ 2.38 (6H, s), 2.42 (3H, s), 3.70 (2H, broad), 6.72 (1H, dd, J = 2.4 Hz, 8.1 Hz), 6.89 (1H, d, J = 2.4 Hz),



7.05 (1H, s), 7.07 (1H, d, J = 8.1 Hz), 7.36 (2H, s)


I-84
δ 2.37 (6H, s), 3.90 (2H, broad-s), 6.96-7.01 (1H, m), 7.10 (1H, t, J = 7.8 Hz), 7.36 (2H, s),



7.43-7.47 (1H, m), 7.86 (1H, d, J = 13.2 Hz)


I-85
δ 2.33 (6H, s), 6.99 (1H, dt, J = 1.5 Hz, 7.8 Hz), 7.10 (1H, t, J = 7.8 Hz), 7.43 (2H, s), 7.46 (1H, d, J = 7.8 Hz),



7.84 (1H, d, J = 13.2 Hz)


I-86
δ 2.33 (6H, s), 3.93 (2H, s), 7.05-7.14 (1H, m), 7.17-7.21 (1H, m), 7.31 (1H, s), 7.35 (2H, s),



7.37-7.40 (1H, m)


I-87
δ 2.35 (6H, s), 3.74 (2H, broad-s), 6.77-6.83 (1H, m), 7.01 (1H, dd, J = 8.8 Hz, 11.7 Hz), 7.35 (2H, s),



7.42 (1H, dd, J = 2.9 Hz, 6.6 Hz), 8.01 (1H, d, J = 15.6 Hz)


I-88
δ 2.40 (6H, s), 4.27 (2H, broad-s), 6.88 (1H, dd, J = 1.5 Hz, 7.8 Hz), 7.03 (1H, dd, J = 1.5 Hz, 7.8 Hz),



7.16 (1H, t, J = 7.8 Hz), 7.29 (1H, s), 7.36 (2H, s)


I-89
δ 2.33 (6H, s), 4.27 (2H, broad-s), 7.15 (1H, d, J = 8.1 Hz), 7.35-7.38 (5H, m)


I-90
δ 2.39 (6H, s), 3.85 (2H, broad-s), 6.72 (1H, dd, J = 2.7 Hz, 8.5 Hz), 7.15 (1H, d, J = 2.7 Hz), 7.22 (1H, d,



J = 8.5 Hz), 7.36 (2H, s), 7.66 (1H, s)


I-91
δ 2.43 (6H, s), 4.34 (2H, broad), 6.86 (1H, dd, J = 1.5 Hz, 8.3 Hz), 6.96 (1H, dd, J = 1.5 Hz, 8.3 Hz),



7.13 (1H, s), 7.19 (1H, t, J = 8.3 Hz), 7.36 (2H, s)


I-92
δ 2.44 (6H, s), 3.86 (2H, broad-s), 6.52 (1H, dd, J = 2.9 Hz, 8.5 Hz), 6.91 (1H, d, J = 2.9 Hz), 7.12 (1H, s),



7.35 (2H, s), 7.62 (1H, d, J = 8.5 Hz)


I-93
δ 2.27 (6H, s), 4.09 (2H, broad-s), 7.08 (1H, s), 7.33 (2H, s), 7.37 (1H, s), 7.43 (1H, s), 7.83 (1H, s)


I-94
(DMSO-d6) δ 2.29 (3H, s), 2.33 (6H, s), 5.43 (2H, s), 6.57-6.59 (1H, m), 6.85-6.90 (1H, m), 7.01 (1H,



t, J = 7.8 Hz), 7.49 (2H, s).


I-95
(DMSO-d6) δ 2.32 (6H, s), 2.76 (3H, d, J = 4.9 Hz), 5.84 (1H, broad), 6.77-6.81 (2H, m), 7.10 (1H, t, J = 7.8 Hz),



7.43 (2H, s), 9.90 (1H, s).


I-96
(DMSO-d6) δ 2.33 (6H, s), 2.76 (3H, d, J = 4.9 Hz), 4.55 (3H, s), 6.58-6.62 (1H, m), 6.70-6.78 (1H, m),



7.13 (1H, t, J = 7.8 Hz), 7.31 (1H, s), 7.50 (2H, s).


I-98
(DMSO-d6) δ 2.32 (6H, s), 2.77 (3H, d, J = 4.9 Hz), 5.82 (1H, broad), 6.79 (1H, t, J = 7.8 Hz),



7.08-7.21 (2H, m), 7.42 (2H, s), 9.88 (1H, s).


 I-124
(DMSO-d6) δ 2.26 (6H, s), 7.46 (2H, s), 7.88 (1H, t, J = 7.8 Hz), 8.43-8.48 (2H, m), 8.73 (1H, s), 8.81 (1H,



s), 10.27 (1H, s).


 I-125
δ 2.16 (6H, s), 7.23 (1H, s), 7.53 (2H, s), 7.73 (1H, t, J = 7.8 Hz), 8.45 (1H, d, J = 7.8 Hz), 8.55 (1H, d, J = 7.8 Hz),



9.05 (1H, t, J = 2.0 Hz).


 I-204
(DMSO-d6) δ 2.35 (6H, s), 4.31 (2H, broad), 6.84-6.87 (1H, m), 7.21-7.25 (1H, m), 7.29-7.31 (2H, m),



7.47-7.49 (2H, m), 7.83 (1H, s), 8.94 (1H, s).


 I-351
(DMSO-d6) δ 2.26 (6H, s), 7.44 (2H, s), 7.51-7.63 (4H, m), 7.74 (1H, d, J = 7.8 Hz), 7.98-8.07 (3H, m),



8.35 (1H, s), 8.71 (1H, s), 9.90 (1H, s), 10.47 (1H, s).


 I-358
(DMSO-d6) δ 2.34 (6H, s), 7.21 (1H, dd, J = 8.2, 11.2 Hz), 7.32 (1H, t, J = 7.8 Hz), 7.49-7.56 (4H, m),



7.78 (1H, d, J = 7.8 Hz), 8.04-8.08 (2H, m), 8.23 (1H, s), 8.71 (1H, s), 9.08 (1H, d, J = 11.2 Hz).


 I-419
(DMSO-d6) δ 2.34 (6H, s), 7.49-7.63 (6H, m), 7.76 (1H, d, J = 7.8 Hz), 7.99-8.08 (3H, m), 8.37 (1H, s),



9.99 (1H, s), 10.48 (1H, s).



















TABLE 12







Comp. No.
LC-MS molecular Ion Peak









I-384
573.80



I-385
573.73



I-401
579.67



I-406
516.73



I-414
654.73



I-418
499.87










The insecticide containing the compound represented by Formula (1) of the invention as an active ingredient is suitable for controlling various pests which give damage to paddy rices, fruit trees, vegetables, other crops and flowers and ornamental plants in agricultural, horticultural or stored grain products, or sanitary pests, or for controlling and it may include vermin such as eelworm, for example, those having strong insecticidal effect against Lepidoptera such as cotton caterpillar (Diaphania indica), oriental tea tortrix (Homona magnanima), cabbage webworm (Hellulla undalis), summer fruit tortrix(Adoxophyes orana fasciata), smaller tea tortrix (Adoxophyes sp.), apple tortrix (Archips fuscocupreanus), peach fruit moth (Carposina niponensis), Manchurian fruit moth (Grapholita inopinata), oriental fruit moth (Grapholita molesta), soybean pod borer (Leguminivora glycinivorella), mulberry leafroller (Olethreutes mori), citrus leafminer (Phyllocnistis citrella), persimmon fruit moth (Stathmopoda masinissa), tea leafroller (Caloptilia theivora), (Caloptilia zachrysa), apple leafminer (Phyllonorycter ringoniella), pear barkminer (Spulerrina astaurota), small citrus dog (Papilio xuthus), common cabbage worm (Pieris rapae crucivora), tobacco budworm (Heliothis armigera), codling moth (Cydia pomonella), diamondback moth (Plutella xylostella), apple fruit moth (Argyresthia conjugella), peach fruit moth (Carposina niponensis), rice stem borer (Chilo suppressalis), rice leafroller (Cnaphalocrocis medinalis), tobacco moth (Ephestia elutella), mulberry pyralid (Glyphodes pyloalis), paddy borer (Scirpophaga incertulas), rice skipper (Parnara guttata), rice armyworm (Pseudaletia separata), pink borer (Sesamia inferens), cabbage armyworm (Mamestra brassicae), common cutworm (Spodoptera litura), beet armyworm (Spodoptera exigua), black cutworm (Agrotis ipsilon), turnip moth (Agrotis segetum), beet semi-looper (Autographa nigrisigna), cabbage looper (Trichoplusia ni); Hemiptera such as aster leafhopper (Macrosteles fascifrons), green rice leafhopper (Nephotettix cincticeps), brown rice planthopper (Nilaparvata lugens), small brown planthopper (Laodelphax striatellus), whitebacked rice planthopper (Sogatella furcifera), citrus psylla (Diaphorina citri), grape whitefly (Aleurolobus taonabae), silverleaf whitefly (Bermisia argentifolii), sweetpotato whitefly (Bemisia tabaci), greenhouse whitefly (Trialeurodes vaporariorum), turnip aphid (Lipaphis erysimi), cotton aphid (Aphis gossypii), apple aphid (Aphis Citricola), green peach aphid (Myzus persicae), Indian wax scale (Ceroplastes ceriferus), Comstock mealybug (Pseudococcus Comstocki), Japanease mealybug (Planococcus kraunhiae), cottony citrus scale (Pulvinaria aurantii), camphor scale (Pseudaonidia duplex), san Jose scale (Comstockaspis perniciosa), arrowhead scale (Unaspis yanonensis), brownwinged green bug (Plautia Stali), brown marmorated stink bug (Halyomorpha mista); Coleoptera such as soybean beetle (Anomala rufocuprea), Japanese beetle (Popillia japonica), cigarette beetle (Lasioderma serricorne), powderpost beetle (Lyctusbrunneus), twenty-eight-spotted ladybird (Epilachna vigintioctopunctata), adzuki bean weevil (Callosobruchus chinensis), vegetable weevil (Listroderes costirostris), maize weevil (Sitophilus zeamais), boll weevil (Anthonomus grandis), rice water weevil (Lissorhoptrus oryzophilus), cucurbit leaf beetle (Aulacophora femoralis), rice leaf beetle (Oulema oryzae), striped flea beetle (Phyllotreta striolata), pine shoot beetle (Tomicus piniperda), Colorado potato beetle (Leptinotarsa decemlineata), Mexican bean beetle (Epilachna varivestis), corn rootworm (Diabrotica sp.), yellowspotted longicorn beetle (Psacothea hilaris), whitespotted longicorn beetle (Anoplophora malasiaca); Diptera such as melon fly (Dacus(Bactrocera) dorsalis), rice leafminer (Agromyza oryzae), onion maggot (Delia antiqua), seedcorn maggot (Delia platura), soybean pod gall midge (Asphondylia sp.), house fly (Musca domestica), garden pea leafminer (Chromatomyia horticola), legume leafminer (Liriomyza trifolii), bryony leafminer (Liriomyza bryoniae), common house mosquito (Culex pipiens); Nematoda such as coffee root-lesion nematode (Pratylenchus coffeae), root-lesion nematode (Pratylenchus sp.), potato cyst nematode (Globodera rostochiensis), root-knot nematode (Meloidogyne sp.), citrus nematode (Tylemchulus semipenetrans), nematode (Aphelenchus avenae), chrysanthemum foliar nematode (Aphelenchoides ritzemabosi); Thysanoptera such as melon thrips (Thrips palmi), western flower thrips (Frankliniella occidentalis), yellow tea thrips (Scirtothrips dorsalis), honeysuckle thrips (Thrips flavus), onion thrips (Thrips tabaci); Orthoptera such as German cockroach (Blattella germanica), American cockroach (Periplaneta americana), rice grasshopper (Oxya yezoensis) and the like.


The insecticides containing the compound represented by Formula (1) of the invention as an active ingredient have notable insecticidal effect against the above-described pests that damage various lowland crops, upland crops, fruit trees, vegetables, other crops and horticultural products. Thus, the insecticidal effect of the invention can be obtained by treating the paddy field water, plant stems and leaves, or soil of the crops of lowland, upland, fruit trees, vegetables, other crops, and flowers and ornamental plants, during the seasons expected of the appearance of such pests, or before or at the point of pest appearance.


The insecticides of the invention are in general used in appropriate formulation forms according to the use, prepared by conventional methods for preparation of agricultural and horticultural chemicals. That is, the compounds represented by Formula (1) may be used in suitable formulations, such as a suspension, an emulsion, a liquid formulation, a water-dispersible powder, a granule, a dust formulation, tablets and the like, prepared by blending the compounds with suitable inert carriers, or with auxiliary agents if necessary, in appropriate proportions, followed by dissolution, separation, suspension, mixing, impregnation, adsorption or adhesion of the ingredients.


The inert carrier that can be used in the invention may be solids or liquids and include, in particular, soybean powders, grain powders, wood powders, bark powders, coarse powders, tobacco powders, walnut shell powders, brans, cellulose powders, residues from plant extraction, synthetic polymers such as pulverized synthetic resins, clays (for example, kaolin, bentonite, acidic white clay), talc (for examples, talc, pyrophyllite, etc.), silica (for examples, diatomite, sand, mica, white carbon (hydrous silica powders, hydrous silica powders called synthetic high dispersity silicic acids, there are also products containing calcium silicate as main component)), activated carbon, sulfur powder, pumice, calcined diatomaceous powders, pulverized bricks, fly ash, sand, inorganic mineral powders such as calcium carbonate and calcium phosphate, chemical fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and ammonium chloride, a compost and the like, which are used alone or as mixtures of two or more.


Materials that can be used as the inert carrier for liquids are selected from those having the function as solvent, as well as those capable of dispersing the active ingredient compound under an aid of an auxiliary agent even if the inert carrier has not the function as solvent, and they can be exemplified by, for example, the carriers listed below: water, alcohols (e.g., methanol, ethanol, isopropanol, butanol, ethylene glycol, etc.), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutylketone, cyclohexanone, etc.), ethers (e.g., diethyl ether, dioxane, cellosolve, diisopropyl ether, tetrahydrofuran, etc.), aliphatic hydrocarbons (e.g., kerosene, mineral oil, etc.), aromatic hydrocarbons (e.g., benzene, toluene, xylene, solvent naphtha, alkyl naphthalene, etc.), halogenated hydrocarbons (e.g., dichloromethane, chloroform, tetrachlorocarbon, chlorobenzene, etc.), esters (e.g., ethyl acetate, butyl acetate, ethyl propionate, diisobutyl phthalate, dibutyl phthalate, dioctyl phthalate, etc.), amides (e.g., dimethyl formamide, diethyl formamide, dimethyl acetamide, etc.), and nitriles (e.g., acetonitrile, etc.), which are used alone or as mixtures of two or more.


The auxiliary agent may include the following representative auxiliary agents, which are used alone or in combination of two or more of them depending on the purpose; however, it is also possible not to use any auxiliary agent.


For the purpose of emulsification, dispersion, solubilization and/or wetting of the active ingredient compound, surfactants can be used, for example, polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleates, alkyl aryl sulfonate, naphthalene sulfonate, lignin sulfonate, higher alcohol sulfonate esters and the like.


For the purpose of dispersion stabilization, adhesion and/or binding of the active ingredient compound, the following auxiliary agent can be use, for example, casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose, gum Arabic, polyvinyl alcohol, pine root oil, corn oil, bentonite, xanthan gum, lignin sulfonate salts and the like.


For the purpose of improving the flowability of solid products, the auxiliary agents can be used, for example, wax, stearic acid salts, phosphoric alkyl esters and the like. An auxiliary agent such as a naphthalene sulfonate condensation product, or a condensed phosphate salt can be used as a suspending agent in suspensions. An antifoaming agent such as silicone oils can be also used as an auxiliary agent.


In addition, the compound represented by Formula (1) of the invention is stable against light, heat, oxidation and the like, but if desired, more stable compositions may obtained by adding a stabilizer. The stabilizer may include, for example, antioxidants or UV absorbents, phenol derivatives such as BHT (2,6-di-t-butyl-4-methyl phenol), BHA (butyl hydroxy anisole), bisphenol derivatives, and aryl amines such as phenyl-α-naphthyl amine, phenyl-β-naphthyl amine, condensation product of phenetidine and acetone, or benzophenone compounds.


The effective amount of the compound represented by Formula (1) of the invention is typically 0.5 to 20% by weight in a dust formulation, 5 to 50% by weight in an emulsion, 10 to 90% by weight in a water-dispersible powder, 0.1 to 20% by weight in a granule, and 10 to 90% by weight in a flowable formulation. Meanwhile, the amount of carrier in the respective formulations is typically 60 to 99% by weight in a dust formulation, 40 to 95% by weight in an emulsion, 10 to 90% by weight in a water-dispersible powder, 80 to 99% by weight in a granule, and 10 to 90% by weight in a flowable formulation. The amount of such auxiliary agent is typically 0.1 to 20% by weight in a dust formulation, 1 to 20% by weight in an emulsion, 0.1 to 20% by weight in a water-dispersible powder, 0.1 to 20% by weight in a granule, and 0.1 to 20% by weight in a flowable formulation.


In order to control various pests, an amount effective for blight control can be applied, just as it is, or as an adequate dilution with water, or as a suspension, to the crops expected of the appearance of the corresponding pests or to the places where such occurrence is not preferable. The amount of use depends on various factors such as, for example, the purpose, the pest to be controlled, the state of plant growth, trend of pest appearance, climate, environmental conditions, formulation, method of use, place of use, timing of use and the like, but it is preferable to use the active ingredient in the concentration of 0.0001 to 5000 ppm, and preferably 0.01 to 1000 ppm. The dose that can be used in approximately 10 a is generally in the range of 1 to 300 g of the active ingredient.


The insecticide of the invention containing the compound represented by Formula (1) as an active ingredient may be used alone in control of various pests in agricultural, horticultural and stored grain products, which damage the rice plants, fruit trees, vegetables, other crops and flowers, or sanitary pests or eelworms, and further in order to obtain superior control effect with respect to various pests which occur at the same time, it may be used in combination with at least one other insecticide and/or fungicide.


Examples of other insecticides which can be combined with the compound represented by Formula (1) of the invention may include, for example, pyrethroid insecticides such as allethrin, tetramethrin, resmethrin, phenothrin, furamethrin, permethrin, cypermethrin, deltamethrin, cyhalothrin, cyfluthrin, fenpropathrin, tralomethrin, cycloprothrin, flucythrinate, fluvalinate, acrinathrin, tefluthrin, bifenthrin, empenthrin, beta-cyfluthrin, zeta-cypermethrin, fenvalerate and the like, and various isomers thereof; or Dalmatian pyrethrum extract; organophosphate insecticides such as DDVP, cyanophos, fenthion, fenitrothion, tetrachlorvinphos, dimethylvinphos, propaphos, methylparathion, temephos, phoxim, acephate, isofenphos, salithion, DEP, EPN, ethion, mecarbam, pyridafenthion, diazinon, pirimiphos-methyl, etrimfos, isoxathion, quinalphos, chlorpyrifos-methyl, chlorpyrifos, phosalone, phosmet, methidathion, oxydeprofos, vamidothion, malathion, phenthoate, dimethoate, formothion, thiometon, disulfoton, phorate, terbufos, profenofos, prothiofos, sulprofos, pyraclofos, monocrotofos, naled, fosthiazate, cadusafos; carbamate insecticides such as NAC, MTMC, MIPC, BPMC, XMC, PHC, MPMC, ethiofencarb, bendiocarb, pirimicarb, carbosulfan, benfuracarb, methomyl, oxamyl, aldicarb; arylpropylether insecticides such as etofenprox, halfenprox; silylether compounds such as silafluofen; insecticidal natural products such as nicotine-sulfate, polynactins, abamectin, milbemectin, BT; insecticides such as cartap, thiocyclam, bensultap, diflubenzuron, chlorfluazuron, teflubenzuron, triflumuron, flufenoxuron, flucycloxuron, hexaflumuron, fluazuron, imidacloprid, nitenpyram, acetamiprid, dinotefuran, pymetrozine, fipronil, buprofezin, fenoxycarb, pyriproxyfen, methoprene, hydroprene, kinoprene, endosulfan, diafenthiuron, triazamate, tebufenozide, benzoepin; acaricides such as dicofol, chlorobenzilate, phenisobromolate, tetradifon, CPCBS, BPPS, chinomethionate, amitraz, benzomate, hexythiazox, fenbutatin oxide, cyhexatin, dienochlor, clofentezine, pyridaben, fenpyroximate, fenazaquin, tebufenpyrad; novaluron, noviflumuron, emamectin benzoate, clothianidin, thiacloprid, thiamethoxam, flupyrazofos, acequinocyl, bifenazate, chromafenozide, etoxazole, fluacrypyrim, flufenzine, halofenozide, indoxacarb, methoxyfenozide, spirodiclofen, tolfenpyrad, gamma-cyhalothrin, ethiprole, amidoflumet, bistrifluron, flonicamid, flubrocythrinate, flufenerim, pyridalyl, pyrimidifen, spinosad, or spiromesifen.


Examples of the fungicides which can be combined with the compound represented by Formula (1) of the invention may include, for example, azole fungicides such as triadimefon, hexaconazole, propiconazole, ipconazole, prochloraz, triflumizole; pyrimidine fungicides such as pyrifenox, fenarimol; anilinopyrimidine fungicides such as mepanipyrim, cyprodinil; acylalanine fungicides such as metalaxyl, oxadixyl, benalaxyl; benzimidazole fungicides such as thiophanate-methyl, benomyl; dithiocarbamate fungicides such as mancozeb, propineb, zineb, metiram; organochlorine fungicides such as tetrachloroisophthalonitrile; carboxamide fungicides such as carpropamid, ethaboxam; morpholine fungicides such as dimethomorph; strobilurin fungicides such as azoxystrobin, kresoxim-methyl, metominostrobin, orysastrobin, fluoxastrobin, trifloxystrobin, dimoxystrobin, pyraclostrobin, picoxystrobin; dicarboximide fungicides such as iprodione, procymidone; soil-applied fungicides such as flusulfamide, dazomet, methyl isothiocyanate, chloropicrin; copper fungicides such as basic copper chloride, basic copper sulfate, copper nonylphenol sulfonate, oxine-copper; inorganic fungicides such as sulfur, zinc sulfate; organophosphate fungicides such as edifenphos, tolclofos-methyl, fosetyl; melanin biosynthesis inhibitors such as phthalide, tricyclazole, pyroquilon, diclocymet; antibiotics such as kasugamycin, validamycin, polyoxins; fungicidal natural products such as rape seed oil; fungicides such as benthiavalicarb-isopropyl, iprovalicarb, cyflufenamid, fenhexamid, quinoxyfen, spiroxamine, diflumetorim, metrafenone, picobenzamid, proquinazid, silthiofam, oxpoconazole, famoxadone, cyazofamid, fenamidone, furametpyr, zoxamide, boscalid, tiadinil, simeconazole, chlorothalonil, cymoxanil, captan, dithianon, fluazinam, folpet, dichlofluanid, (RS)—N-[2-(1,3-dimethylbutyl)thiophen-3-yl]-1-methyl-3-trifluoro methyl-1H-pyrazole-4-carboxamide (penthiopyrad: ISO proposed), oxycarboxin, mepronil, flutolanil, triforine, oxolinic acid, probenazole, acibenzolar-S-methyl, isoprothiolane, ferimzone, diclomezine, pencycuron, fluoroimide, chinomethionate, iminoctadine-triacetate, iminoctadine-albesilate and the like.


When the compound represented by Formula (1) of the invention is used in combination with at least one other insecticide and/or fungicide, a mixed composition of the compound represented by Formula (1) and other insecticide and/or fungicide may be used, or the compound represented by Formula (1) and other insecticide/fungicide may be mixed and used at the time of apply.


In addition to the above-mentioned insecticides and fungicides, the compound represented by Formula (1) can be mixed with plant protecting agents such as a herbicide, a fertilizer, a soil reformer, a plant growth controlling agent and a material, in order to form multi-purpose compositions of high efficacy, which are expected to provide an additive effect or a synergistic effect.


The following Examples illustrate representative Examples of the invention, but they are not intended to limit the invention.


Example 1-1
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-nitrobenzamide

To a solution prepared by adding 20.0 g of 2,6-dimethyl-4-heptafluoroisopropylaniline and 11.0 g of pyridine to 100 ml of tetrahydrofuran at room temperature with stirring, 13.0 g of 3-nitrobenzoyl chloride dissolved in 20 ml of tetrahydrofuran was gradually added dropwise thereto. After the reaction solution was stirred at room temperature for 10 hours, ethyl acetate and water were added thereto. Phase separation was carried out, and then the organic layer was separated and dried over anhydrous magnesium sulfate. This solution was filtered, the filtrate was collected, and the solvent was distilled off under reduced pressure. Thus obtained residue was washed with a solvent mixture of hexane-diisopropyl ether to give 26.0 g (yield 85%) of the title compound as a white solid.



1H-NMR (CDCl3, ppm) δ 2.33 (6H, s), 7.37 (2H, s), 7.68 (1H, s), 7.72 (1H, t, J=8.1 Hz), 8.28 (1H, d, J=8.1 Hz), 8.44 (1H, dd, J=1.2, 8.1 Hz), 8.75 (1H, t, J=1.2 Hz).


Example 1-2
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide (Compound No. 1-2)

To a solution prepared by adding 0.90 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-nitrobenzamide and 1.56 g of anhydrous tin(II) chloride to 25 ml of ethanol at room temperature with stirring, 2 ml of concentrated hydrochloric acid was added and the mixture was stirred at 60° C. for one hour. After brought back to room temperature, the reaction solution was poured onto water, and neutralization was carried out using potassium carbonate. Ethyl acetate was added, the insolubles were filtered off, and then the organic layer was separated and dried over anhydrous magnesium sulfate. This solution was filtered, the filtrate was collected, and the solvent was distilled off under reduced pressure. Thus obtained residue was washed with hexane to give 0.44 g (yield 53%) of the title compound as a white solid.



1H-NMR (CDCl3, ppm) δ 2.34 (6H, s), 3.87 (2H, broad), 6.86-6.89 (1H, m), 7.20-7.35 (6H, m)


Example 1-3
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(benzoylamino)benzamide (Compound No. 10)

To a solution prepared by adding 0.25 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide and 0.06 g of pyridine to 5 ml of tetrahydrofuran at room temperature with stirring, 0.09 g of benzoyl chloride dissolved in 1 ml of tetrahydrofuran was added dropwise. After stirring at room temperature for 1 hour, ethyl acetate and 1N hydrochloric acid were added to the reaction solution, and the organic layer was separated. The organic layer was washed once with saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate. This solution was filtered, the filtrate was collected, and the solvent was distilled off under reduced pressure. Thus obtained solid was washed with diisopropyl ether to give 0.29 g (yield 92%) of the title compound as a white solid.



1H-NMR (DMSO-d6, ppm) δ 2.37 (6H, s), 7.34 (2H, s), 7.46-7.57 (4H, m), 7.75 (1H, d, J=7.8 Hz), 7.98-8.01 (2H, m), 8.12 (1H, d, J=7.3 Hz), 8.34 (1H, s), 8.87 (1H, s), 9.66 (1H, s).


Example 2-1
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl-N-methyl 3-nitrobenzamide

To a suspension of 0.18 g of 60% sodium hydride in 15 ml of tetrahydrofuran, 2.0 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-nitrobenzamide dissolved in 5 ml of tetrahydrofuran was added dropwise at room temperature. After the mixture was stirred at room temperature for 30 minutes, 0.65 g of methyl iodide dissolved in 5 ml of tetrahydrofuran was added dropwise. Then, after raising temperature to 50° C. and stirred for 4 hours, the reaction solution was returned to room temperature, and ethyl acetate and water were added. The organic layer was separated, washed once with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Thus obtained residue was purified by silica gel column chromatography (eluent:hexane:ethyl acetate=6:1) to give 1.73 g (yield 84%) of the title compound as a white solid.



1H-NMR (CDCl3, ppm) δ 2.31 (6H, s), 3.38 (3H, s), 7.27 (2H, s), 7.37 (1H, t, J=7.8 Hz), 7.62-7.65 (1H, m), 8.05 (1H, t, J=2.0 Hz), 8.11-8.14 (1H, m).


Example 2-2
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl-N-methyl 3-aminobenzamide (Compound No. 1-5)

A solution prepared by adding 1.50 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl-N-methyl 3-nitrobenzamide and 0.15 g of 10% palladium-carbon to 20 ml of methanol, was stirred under a hydrogen atmosphere at atmospheric pressure for 2 hours. After the catalyst was filtered off, the solvent was distilled off under reduced pressure. Then, thus obtained solid was washed with hexane to give 1.24 g of the title compound (yield 88%) as a white solid.



1H-NMR (CDCl3, ppm) δ2.27 (6H, s), 3.31 (3H, s), 3.80 (2H, broad), 6.40-6.43 (1H, m), 6.54-6.58 (1H, m), 6.71 (1H, t, J=2.0 Hz), 6.76-6.86 (1H, m), 7.22 (2H, s).


Example 2-3
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl-N-methyl 3-(benzoylamino)benzamide (Compound No. 1478)

The title compound, was prepared as a white solid according to the conditions described in Example 1-3.



1H-NMR (DMSO-d6, ppm) δ 2.29 (6H, s), 3.24 (3H, s), 6.84 (1H, d, J=7.8 Hz), 7.12 (1H, t, J=7.8 Hz), 7.33 (2H, s), 7.50-7.64 (4H, m), 7.85-7.88 (2H, m), 7.98-8.03 (1H, m), 10.22 (1H, s).


Example 3
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-[(2-chloropyridin-3-yl)carbonylamino]benzamide (Compound No. 106)

To a solution prepared by adding 0.6 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide and 0.4 g of pyridine to 10 ml of tetrahydrofuran, 0.35 g of 2-chloronicotinoyl chloride hydrochloride was added and the mixture was stirred at room temperature for 4 hours. Ethyl acetate was added, the mixture was twice washed with saturated sodium hydrogen carbonate solution, and the solvent was distilled off under reduced pressure. Thus obtained solid was washed with a solvent mixture of hexane-diisopropyl ether and dried to give 0.64 g (yield 75%) of the title compound as a white solid.



1H-NMR (DMSO-d6, ppm) δ 2.30 (6H, s), 7.45 (2H, s), 7.54-7.60 (2H, m), 7.77-7.80 (1H, m), 7.95 (1H, d J=7.8 Hz), 8.10-8.12 (1H, m), 8.30 (1H, s), 8.54-8.59 (1H, m), 10.03 (1H, s), 10.88 (1H, s).


Example 4
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-[(pyridin-3-yl)carbonylamino]benzamide (Compound No. 101)

A solution prepared by adding 99 mg of nicotinic acid and 153 mg of 1,1′-oxalyl diimidazole to 10 ml of acetonitrile was stirred at room temperature for 15 minutes and again at 40° C. for 40 minutes. After returning back to room temperature, 300 mg of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide was added, and the mixture was stirred at 60° C. for 5 hours. Then, the solvent was distilled off under reduced pressure, and to the residue obtained therefrom, ethyl acetate was added. The organic layer was twice washed with saturated sodium hydrogen carbonate solution, and the solvent was again distilled off under reduced pressure. Thus obtained residue was purified by silica gel column chromatography (eluent:hexane:ethyl acetate=1:3) to give 70 mg (yield 18%) of the title compound as a white solid.



1H-NMR (DMSO-d6, ppm) δ 2.30 (6H; s), 7.45 (2H, s), 7.54-7.61 (2H, m), 7.78 (1H, d, J=8.3 Hz), 8.06 (1H, d, J=7.3 Hz), 8.32-8.35 (2H, m), 8.77-8.79 (1H, m), 9.15 (1H, d, J=1.5 Hz), 10.00 (1H, s), 10.66 (1H, s).


Example 5-1
Preparation of N-methyl-2-bromo-4-heptafluoroisopropyl-6-methylaniline

To a solution prepared by adding 1.0 g of N-methyl-4-heptafluoroisopropyl-2-methylaniline to 5 ml of N,N-dimethyl formamide, 0.8 g of N-bromosuccinimide dissolved in 3 ml of N,N-dimethyl formamide was added dropwise. After the mixture was stirred at room temperature for 5 hours, ethyl acetate and water were added, and the organic layer was separated. The organic layer was twice washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Thus obtained residue was purified by silica gel column chromatography (eluent:hexane:ethyl acetate=9:1) to give 0.86 g (yield 68%) of the title compound as a red oil.



1H-NMR (CDCl3, ppm) δ 2.41 (3H, s), 2.93 (3H, s), 3.90 (1H, broad), 7.23 (1H, s), 7.54 (1H, s).


Example 5-2
Preparation of N-(2-bromo-4-heptafluoroisopropyl-6-methyl)phenyl-N-methyl 3-(benzoylamino)benzamide (Compound No. 1479)

The title compound was prepared as a white solid from N-methyl-2-bromo-4-heptafluoroisopropyl-6-methylaniline according to the conditions described in Examples 1-2 and 1-3.



1H-NMR (DMSO-d6, ppm) δ 2.41 (3H, s), 3.25 (3H, s), 6.95 (1H, dd, J=1.5, 7.8 Hz), 7.16 (1H, t, J=7.8 Hz), 7.50-7.64 (4H, m), 7.68 (1H, s), 7.86-7.88 (2H, m), 7.93 (1H, t, J=1.5 Hz), 7.98-8.00 (1H, m), 10.24 (1H, s).


Example 6
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl-N-methyl 3-(N-methylbenzoylamino)benzamide (Compound No. 1487)

To a suspension of 40 mg of 60% sodium hydride in 10 ml of tetrahydrofuran, 0.3 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl-N-methyl 3-(benzoylamino)benzamide dissolved in 5 ml of tetrahydrofuran was added dropwise at room temperature. After the mixture was stirred at room temperature for 1 hour, 0.16 g of methyl iodide dissolved in 5 ml of tetrahydrofuran was added dropwise. Then, after returning to a temperature to 50° C. and stirred for 4 hours, the reaction solution was returned to room temperature, and ethyl acetate and water were added to the reaction solution. The organic layer was separated, washed once with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Thus obtained residue was washed with diisopropyl ether to give 1.73 g (yield 84%) of the title compound as a white solid.



1H-NMR (DMSO-d6, ppm) δ 2.20 (6H, s), 3.08 (3H, s), 3.20 (3H, s), 6.93-7.39 (10H, m), 7.45-7.51 (1H, m).


Example 7-1
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzthioamide

0.35 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide and 0.19 g of Lawesson's reagent was added to 10 ml of toluene, and the mixture was heated with stirring at reflux temperature for 6 hours. The reaction solution was concentrated under reduced pressure, the solvent was distilled off, and thus obtained residue was purified by silica gel column chromatography (eluent:hexane:ethyl acetate=3:1) to give 0.07 g (yield 20%) of the title compound.



1H-NMR (CDCl3, ppm) δ2.36 (6H, s), 3.87 (2H, broad-s), 6.84-6.87 (1H, m), 7.18-7.24 (2H, m), 7.33 (1H, s), 7.39 (2H, s), 8.56 (1H, broad-s).


Example 7-2
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(benzoylamino)benzthioamide (Compound No. 2201)

The title compound was prepared from N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzthioamide according to the conditions described in Example 1-3.



1H-NMR (CDCl3, ppm) δ 2.38 (6H, s), 7.25-8.00 (11H, m), 8.34 (1H, s), 8.85 (1H, broad.).


Example 8
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(phenylthiocarbonylamino)benzamide (Compound No. 2202) and N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(phenylthiocarbonylamino)benzthioamide (Compound No. 2203)

A solution of 0.37 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(benzoylamino)benzamide and 0.30 g of Lawesson's reagent in 10 ml of toluene was stirred at 70° C. for 6 hours. The reaction solution was concentrated under reduced pressure, and thus obtained residue was purified by silica gel column chromatography (eluent:hexane:ethyl acetate=3:1) to give 0.18 g (yield 47%) of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(phenylthiocarbonylamino)benzamide and 0.05 g (yield 13%) of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(phenylthiocarbonylamino)benzthioamide.


Characterization of Compound No. 2202



1H-NMR (CDCl3, ppm) δ 2.36 (6H, s), 7.37 (2H, s), 7.47-7.61 (5H, m), 7.85-8.03 (4H, m), 8.57 (1H, s), 9.18 (1H, s).


Characterization of Compound No. 2203



1H-NMR (CDCl3, ppm) δ 2.38 (6H, s), 7.41 (2H, s), 7.45-7.55 (4H, m), 7.90-7.96 (4H, m), 8.57 (1H, broad), 8.74 (1H, broad), 9.18 (1H, broad).


Example 9-1
Preparation of N-benzyl-N-(2,6-dimethyl-4-heptrafluoroisopropyl)phenyl 3-nitrobenzamide

The title compound was prepared from N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-nitrobenzamide and benzyl bromide according to the process described in Example 6.


Example 9-2
Preparation of N-benzyl-N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(2-fluorobenzoylamino)benzamide

The title compound was prepared from N-benzyl-N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-nitrobenzamide and 2-fluorobenzoyl chloride according to the processes described in Examples 1-2 and 1-3.


Example 9-3
Preparation of N-benzyl-N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-[N-ethyl-N-(2-fluorobenzoyl)amino]benzamide

The title compound was prepared from N-benzyl-N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(2-fluorobenzoylamino)benzamide and ethyl iodide according to the process described in Example 6.


Example 9-4
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-[N-ethyl-N-(2-fluorobenzoyl)amino]benzamide (Compound No. 1206)

A solution of 1.07 g of N-benzyl-N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-[N-ethyl-N-(2-fluorobenzoyl)amino]benzamide and 0.15 g of 10% palladium-carbon in 10 ml of methanol was stirred at 45° C. for 6 hours under a hydrogen atmosphere. The catalyst was filtered off, and the solvent was distilled off under reduced pressure. Then, thus obtained residue was purified by silica gel (Fuji Silysia Chemical Ltd., NH silica) column chromatography (eluent:hexane:ethyl acetate=1:1) to give 0.30 g (yield 32%) of the title compound as a white solid.



1H-NMR (DMSO-d6, ppm) δ 1.17 (3H, broad), 2.22 (6H, s), 3.99 (2H, broad), 7.01-7.08 (2H, m), 7.29-7.43 (6H, m), 7.72-7.77 (2H, m), 9.90 (1H, s).


Example 10-1
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 2-fluoro-3-nitrobenzamide

2.35 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 2-chloro-3-nitrobenzamide prepared according to the process described in Example 1-1 and 0.87 g of potassium fluoride (spray-dried product) were added to 25 ml of N,N-dimethyl formamide dried by molecular sieves, and the mixture was heated with stirring at 150° C. for 3 hours. After the reaction solution was brought back to room temperature, ethyl acetate and water were added thereto, and phase separation was carried out. The organic layer was separated, washed twice with water and dried over anhydrous magnesium sulfate. This solution was filtered, the filtrate was collected, and the solvent was distilled off under reduced pressure. Thus obtained residue was purified by silica gel chromatography (eluent:hexane:ethyl acetate=4:1) to give 1.02 g (yield 45%) of the title compound as a solid.



1H-NMR (CDCl3, ppm) δ 2.37 (6H, s), 7.39 (2H, s), 7.48-7.53 (1H, m), 7.87 (1H, d, J=11.5 Hz), 8.23-8.28 (1H, m), 8.42-8.46 (1H, m).


Example 10-2
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(benzoylamino)-2-fluorobenzamide (Compound No. 601)

The title compound was prepared according to the processes described in Examples 1-2 and 1-3.



1H-NMR (DMSO-d6, ppm) δ 2.34 (6H, s), 7.37 (1H, t, J=7.8 Hz), 7.45 (2H, s), 7.53-7.65 (4H, m), 7.77-7.82 (1H, m), 8.00-8.02 (2H, m), 10.10 (1H, s), 10.29 (1H, s).


Example 11-1
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 4-fluoro-3-nitrobenzamide

5.22 g of 4-fluoro-3-nitrobenzoic acid and 0.1 g of N,N-dimethyl formamide were introduced to 30 ml of toluene, and 3.7 g of thionyl chloride was added. The reaction mixture was stirred at 80° C. for 1 hour and again for 2 hours under reflux conditions. After cooling to room temperature, the solvent was distilled off under reduced pressure, thus obtained residue was dissolved in 10 ml of tetrahydrofuran, and this solution was added dropwise to a mixed solution of 8.1 g of 2,6-dimethyl-4-heptafluoroisopropylaniline, 4.4 g of pyridine and 20 ml of tetrahydrofuran. After the mixture was stirred for 2 hours, ethyl acetate was introduced, and the organic layer was washed with water and saturated sodium hydrogen carbonate solution sequentially. The organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and thus obtained residue was purified by silica gel column chromatography (eluent:hexane:ethyl acetate=4:1) to give 5.9 g (yield 46%) of the title compound as a white solid.



1H-NMR (CDCl3, ppm) δ 2.11 (6H, s), 7.26-7.31 (3H, m), 8.12-8.15 (1H, m), 8.60-8.62 (1H, m), 8.70 (1H, s).


Example 11-2
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-amino-4-fluorobenzamide

The title compound was prepared according to the conditions described in Example 1-2. The compound was obtained as a white solid.



1H-NMR (DMSO-d6, ppm) δ 2.26 (6H, s), 5.42 (2H, broad-s), 7.10-7.19 (2H, m), 7.37 (1H, dd, J=2.0, 8.8 Hz), 7.42 (2H, s), 9.78 (1H, s).


Example 11-3
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 4-fluoro-3-(methylamino)benzamide

18 ml of 98% sulfuric acid was cooled to a temperature of 0° C. to 5° C. and stirred, and 2.50 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-amino-4-fluorobenzamide was added thereto. After the reaction mixture was stirred for 15 minutes, 18 ml of an aqueous solution of 37% formaldehyde was added dropwise, and the mixture was stirred at 0° C. for 1 hour and for further 3 hours at room temperature. To the reaction solution cooled again to 0° C., 28% ammonia solution in water was added to neutralize the solution, ethyl acetate was added, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and thus obtained residue was purified by silica gel column chromatography (eluent:hexane:ethyl acetate=4:1) to give 1.74 g (yield 67%) of the title compound in an amorphous form.



1H-NMR (CDCl3, ppm) δ 2.32 (6H, s), 2.94 (3H, d, J=4.9 Hz), 4.14 (1H, broad), 7.03 (1H, dd, J=8.3, 11.2 Hz), 7.10-7.13 (1H, m), 7.24 (1H, s), 7.34 (2H, s), 7.42 (1H, s).


The following compounds were prepared according to the process described in Example 11-3:


N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 2-fluoro-3-(methylamino)benzamide


1H-NMR (DMSO-d6) δ 2.32 (6H, s), 2.76 (3H, d, J=4.9 Hz), 5.84 (1H, broad), 6.77-6.81 (2H, m), 7.10 (1H, t, J=7.8 Hz), 7.43 (2H, s), 9.90 (1H, s).


N-[2,6-dimethyl-4-(nonafluoro-2-butyl)]phenyl 2-fluoro-3-(methylamino) benzamide


1H-NMR (DMSO-d6) δ 2.32 (6H, s), 2.77 (3H, d, J=4.9 Hz), 5.82 (1H, broad), 6.79 (1H, t, J=7.8 Hz), 7.08-7.21 (2H, m), 7.42 (2H, s), 9.88 (1H, s).


N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl-N-methyl 2-fluoro-3-(methylamino)benzamide


1H-NMR (DMSO-d6) δ 2.33 (6H, s), 2.76 (3H, d, J=4.9 Hz), 4.55 (3H, s), 6.58-6.62 (1H, m), 6.70-6.78 (1H, m), 7.13 (1H, t, J=7.8 Hz), 7.31 (1H, s), 7.50 (2H, s).


Example 11-4
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 4-fluoro-3-[N-methyl-N-(4-nitrobenzoyl)amino]benzamide (Compound No. 1464)

The title compound was obtained as a white solid using 4-nitrobenzoyl chloride according to the conditions described in Example 1-3.



1H-NMR (DMSO-d6, ppm) δ 2.23 (6H, s), 3.42 (3H, s), 7.41 (1H, broad), 7.45 (2H, s), 7.60 (2H, broad), 7.90 (1H, broad), 8.08-8.13 (3H, broad), 9.93 (1H, s).


Example 12-1
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-chloropyridine-2-carboxamide

A mixture of 2.2 g of 6-chloropyridine-2-carboxylic acid and 0.1 g of N,N-dimethyl formamide was introduced to 10 ml of toluene, and then 2.0 g of thionyl chloride was added thereto. After stirred at 80° C. for 1 hour, the reaction mixture was stirred for another 2 hours under reflux conditions. The mixture was cooled to room temperature, the solvent was distilled off under reduced pressure, and thus obtained residue was added dropwise to a mixed solution of 3.67 g of 2,6-dimethyl-4-heptafluoroisopropylaniline, 1.22 g of pyridine and 20 ml of tetrahydrofuran. After the mixture was stirred at room temperature for 2 hours, ethyl acetate was added thereto, and the organic layer was washed with water and saturated aqueous sodium hydrogen carbonate solution sequentially. The organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and thus obtained residue was washed with cooled hexane at 5° C. to give 4.42 g (yield 77%) of the title compound as a white solid.



1H-NMR (CDCl3, ppm) δ 2.36 (6H, s), 7.36 (2H, s), 7.56 (1H, dd, J=1.0, 8.1 Hz), 7.88 (1H, dd, J=7.6, 8.1 Hz), 8.23 (1H, dd, J=1.0, 7.6 Hz), 9.27 (1H, broad-s).


Example 12-2
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-aminopyridin-2-carboxamide

A mixture of 3.08 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-chloropyridin-2-carboxamide, 30 ml of 28% ammonia solution in water, 0.20 g of copper sulfate and 70 ml of methanol was introduced into a 200 ml autoclave and was heated with stirring at 150° C. for 2 hours. After the mixture was cooled to room temperature, ammonia was distilled off at 60° C. and atmospheric pressure, and methanol was distilled off under reduced pressure. Ethyl acetate and water were added to the reaction solution, phase separation was carried out, and the organic layer was separated and dried over anhydrous sodium sulfate. This solution was filtered, the filtrate was collected, and the solvent was distilled under reduced pressure. Thus obtained residue was purified by silica gel column chromatography (eluent:hexane:ethyl acetate=3:2 to 2:3) to give 2.90 g (yield 98%) of the title compound as an oil.



1H-NMR (CDCl3, ppm) δ2.35 (6H, s), 4.57 (2H, broad-s), 6.69-6.74 (1H, m), 7.34 (2H, s), 7.62-7.66 (2H, m), 9.39 (1H, broad-s).


Example 12-3
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-(benzoylamino)pyridin-2-carboxamide (Compound No. 2001)

A mixture of 0.16 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-aminopyridin-2-carboxamide and 62 mg of pyridine was introduced to 3 ml of tetrahydrofuran, 63 mg of benzoyl chloride was added, and the mixture was stirred at room temperature for 3 hours. Ethyl acetate was introduced, and the organic layer was washed with water and then with saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure, and thus obtained residue was purified by silica gel column chromatography (eluent:hexane:ethyl acetate=6:4) to give 0.13 g (yield 65%) of the title compound as a white solid.



1H-NMR (CDCl3, ppm) δ 2.36 (6H, s), 7.36 (2H, s), 7.53-7.57 (2H, m), 7.61-7.65 (1H, m), 7.95-8.03 (3H, m), 8.08 (1H, dd, J=1.0, 7.3 Hz), 8.52 (1H, broad-s), 8.62 (1H, dd, J=1.0, 8.3 Hz), 9.19 (1H, broad-s).


Example 12-4
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-(benzoylamino)-1-oxopyridin-2-carboxamide (Compound No. 2164)

A mixture of 65 mg of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 6-(benzoylamino)pyridin-2-carboxamide and 0.11 g of m-chloroperbenzoic acid was introduced to 5 ml of benzene, and the mixture was stirred at 80° C. for 4 hours. The mixture was cooled to room temperature, and the organic layer was washed with water and saturated aqueous sodium hydrogen carbonate solution sequentially and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and thus obtained residue was purified by silica gel column chromatography (eluent:hexane:ethyl acetate=4:1) to give 52 mg (yield 52%) of the title compound as a white solid.



1H-NMR (CDCl3, ppm) δ 2.34 (6H, s), 7.47 (2H, s), 7.62-7.65 (2H, m), 7.70-7.81 (2H, m), 8.00-8.04 (3H, m), 8.64 (1H, dd, J=1.5, 8.3 Hz), 10.90 (1H, broad-s), 12.30 (1H, broad-s).


Example 13-1
Preparation of 2,6-dibromo-4-heptafluoroisopropylaniline

To a solution prepared by adding 2.0 g of 4-heptafluoroisopropylaniline in 5 ml of N,N-dimethyl formamide, 2.73 g of N-bromosuccinimide dissolved in 10 ml of N,N-dimethyl formamide was introduced at 5° C. After the reaction solution was returned to room temperature and stirred for 2 hours, ethyl acetate and water were added thereto, and the organic layer was separated and washed once with water. The solvent was distilled off under reduced pressure, and thus obtained residue was purified by silica gel column chromatography (eluent:hexane:ethyl acetate=20:1) to give 2.20 g (yield 69%) of the title compound as an orange oil.



1H-NMR (CDCl3, ppm) δ 4.89 (2H, broad-s), 7.59 (2H, s).


Example 13-2
Preparation of N-(2,6-dibromo-4-heptafluoroisopropyl)phenyl 3-nitrobenzamide

A mixed solution of 2.20 g of 2,6-dibromo-4-heptafluoroisopropylaniline, 1.46 g of 3-nitrobenzoyl chloride and 10 ml of pyridine was stirred at 70° C. for 20 hours. After the solution was returned to room temperature, ethyl acetate and 1N hydrochloric acid were added, and the organic layer was separated and washed with a saturated aqueous sodium hydrogen carbonate solution. The solvent was distilled off under reduced pressure, and thus obtained residue was dissolved in a solvent mixture of 8 ml of tetrahydrofuran and 2 ml of methanol. Then, the solution was cooled to 5° C., 0.30 g of sodium hydroxide was added, the solution was stirred for 2 hours, and ethyl acetate and water were added to the reaction solution. The organic layer was separated, washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and thus obtained residue was washed with hexane to give 2.19 g (yield 73%) of the title compound as a pale brown solid.



1H-NMR (DMSO-d6, ppm) δ 7.92 (1H, t, J=7.8 Hz), 8.08 (2H, s), 8.45 (1H, d, J=7.8 Hz), 8.53 (1H, dd, J=1.5, 7.8 Hz), 8.85 (1H, d, J=1.5 Hz), 11.08 (1H, s).


Example 13-3
Preparation of N-(2,6-dibromo-4-heptafluoroisopropyl)phenyl 3-aminobenzamide

The title product was obtained as a white solid according to the conditions described in Example 1-2.



1H-NMR (DMSO-d6, ppm) δ 5.39 (2H, broad-s), 6.77-6.80 (1H, m), 7.13-7.20 (3H, m), 8.02 (2H, s), 10.35 (1H, s).


Example 13-4
Preparation of N-(2,6-dibromo-4-heptafluoroisopropyl)phenyl 3-(2-fluorobenzoyl)aminobenzamide (Compound No. 8)

The title compound was obtained as a white solid using 2-fluorobenzoyl chloride according to the conditions described in Example 1-3.



1H-NMR (DMSO-d6, ppm) δ 7.33-7.40 (2H, m), 7.55-7.63 (2H, m), 7.68-7.72 (1H, m), 7.78 (1H, d, J=7.8 Hz), 7.99 (1H, d, J=7.8 Hz), 8.05 (2H, s), 8.34 (1H, s), 10.65 (1H, s), 10.69 (1H, s).


Example 14-1
Preparation of 4-(heptafluoro-n-propylthio)aniline

To 20 ml of an acetonitrile solution of 1.25 g of 4-aminothiophenol and 1.11 g of triethylamine, 5.91 g of 1-iodoheptafluoro-n-propane was added, and the mixture was stirred at room temperature for 3 hours. The mixture was diluted with ether, washed with an aqueous solution of 1N sodium hydroxide and purified by silica gel column chromatography (eluent:hexane:ethyl acetate=4:1) to give 1.85 g (yield 63%) of the title compound.



1H-NMR (CDCl3, ppm) δ 3.95 (2H, s), 6.66 (2H, d, J=8.8 Hz), 7.40 (2H, d, J=8.8 Hz).


Example 14-2
Preparation of 2,6-dibromo-4-(heptafluoro-n-propylthio)aniline

To a solution prepared by adding 0.77 g of 4-(heptafluoro-n-propylthio)aniline in 15 ml of N,N-dimethyl formamide, 0.98 g of N-bromosuccinimide was introduced. After the mixture was stirred at 60° C. for 2 hours, ether and water were added, and the organic layer was separated. The organic layer was twice washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Thus obtained residue was purified by silica gel column chromatography (eluent:hexane:ethyl acetate=9:1) to give 1.19 g (yield 100%) of the title compound as a red oil.



1H-NMR (CDCl3, ppm) δ 4.98 (2H, broad-s), 7.66 (2H, s).


Example 14-3
Preparation of N-(2,6-dibromo-4-heptafluoro-n-propylthio)phenyl 3-nitrobenzamide

To a solution prepared by adding 1.08 g of 2,6-dibromo-4-(heptafluoro-n-propylthio)aniline and 0.4 g of pyridine to 20 ml of tetrahydrofuran with stirring at room temperature, 0.55 g of 3-nitrobenzoyl chloride dissolved in 20 ml of tetrahydrofuran was gradually introduced dropwise. After the mixture was stirred at room temperature for 10 hours, ethyl acetate and water were added to the reaction solution. The organic layer was separated and dried over anhydrous magnesium sulfate. This solution was filtered, the filtrate was collected, and the solvent was distilled off under reduced pressure. Thus obtained residue was purified by silica gel column chromatography (eluent:hexane:ethyl acetate=4:1) to give 0.86 g (yield 48%) of the title compound as a white solid.



1H-NMR (CDCl3, ppm) δ 7.73 (1H, s, J=7.8 Hz), 7.77 (1H, t, J=7.8 Hz), 7.96 (2H, s), 8.31 (1H, s), 8.47-8.50 (1H, m), 8.79 (1H, t, J=2.0 Hz).


Example 14-4
Preparation of N-{2,6-dibromo-4-(heptafluoro-n-propylthio)}phenyl 3-aminobenzamide (Compound No. 1-28)

To a solution prepared by adding 0.97 g of N-{2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl 3-nitrobenzamide and 0.95 g of anhydrous tin(II) chloride to 20 ml of ethanol with stirring at room temperature, 2 ml of concentrated hydrochloric acid was added, and the mixture was heated with stirring at 60° C. for 1 hour. After the mixture was returned to room temperature, the reaction solution was poured onto water, and neutralization was carried out using potassium carbonate. Ethyl acetate was added, the insolubles were filtered off, and the organic layer was separated and dried over anhydrous magnesium sulfate. This solution was filtered, the filtrate was collected, and the solvent was distilled off under reduced pressure. Thus obtained residue was washed with hexane to give 0.75 g (yield 81%) of the title compound as a white solid.



1H-NMR (CDCl3, ppm) δ 3.89 (2H, broad-s), 6.90 (1H, dt, J=2.5, 6.4 Hz), 7.28-7.30 (3H, m), 7.60 (1H, s), 7.93 (2H, s).


Example 14-5
Preparation of N-(2,6-dibromo-4-heptafluoro-n-propylthio)phenyl 3-(benzoylamino)benzamide (Compound No. 263)

To a solution prepared by adding 0.10 g of N-(2,6-dibromo-4-heptafluoro-n-propylthio)phenyl 3-aminobenzamide and 0.02 g of pyridine to 5 ml of tetrahydrofuran with stirring at room temperature, 0.03 g of benzoyl chloride dissolved in 1 ml of tetrahydrofuran was introduced. After the mixture was stirred at room temperature for 1 hour, ethyl acetate and 1N hydrochloric acid were added, and the organic layer was separated. The organic layer was washed once with saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate. This solution was filtered, the filtrate was collected, and the solvent was distilled off under reduced pressure. Thus obtained residue was purified by silica gel column chromatography (eluent:hexane:ethyl acetate=3:1) to give 0.10 g (yield 67%) of the title compound as a white solid.



1H-NMR (DMSO-d6, ppm) δ 7.47-7.57 (4H, m), 7.78 (1H, d, J=7.8 Hz), 7.93 (2H, s), 7.99-8.01 (2H, m), 8.18 (1H, d, J=7.8 Hz), 8.33 (1H, t, J=2.0 Hz), 9.27 (1H, s), 9.65 (1H, s).


Example 14-6
Preparation of N-(2,6-dibromo-4-heptafluoro-n-propylthio)phenyl 3-[(2-chloropyridin-3-yl)carbonylamino]benzamide (Compound No. 309)

To a solution prepared by adding 0.15 g of N-(2,6-dibromo-4-heptafluoro-n-propylthio)phenyl 3-aminobenzamide and 0.03 g of pyridine to 5 ml of tetrahydrofuran, 0.05 g of 2-chloronicotinoyl chloride hydrochloride was added, and the mixture was stirred at room temperature for 4 hours. Ethyl acetate was added, the mixture was twice washed with saturated sodium hydrogen carbonate solution, and the solvent was distilled off under reduced pressure. Thus obtained solid was purified by silica gel column chromatography (eluent:hexane:ethyl acetate=3:1) to give 0.17 g (yield 92%) of the title compound in an amorphous form.



1H-NMR (CDCl3, ppm) δ 7.44 (1H, dd, J=4.8, 7.8 Hz), 7.56 (1H, t, J=7.8 Hz), 7.80 (1H, d, J=7.8 Hz), 7.86 (1H, s), 7.92 (1H, d, J=7.8 Hz), 7.95 (2H, s), 8.23 (1H, dd, J=2.0, 7.8 Hz), 8.30 (1H, s), 8.41 (1H, s), 8.55 (1H, dd, J=2.0, 4.8 Hz).


Example 14-7
Preparation of N-(2,6-dibromo-4-heptafluoro-n-propylsulfinyl)phenyl 3-nitrobenzamide

To a solution prepared by adding 0.5 g of N-(2,6-dibromo-4-heptafluoro-n-propylthio)phenyl 3-nitrobenzamide to 15 ml of chloroform and stirring at room temperature, 0.5 g of m-chloroperbenzoic acid was introduced. The mixture was stirred at room temperature for 2 days, and after addition of an aqueous solution of sodium sulfite, the mixture was stirred again. Phase separation was carried out, an obtained organic layer was washed with an aqueous solution of sodium hydroxide and saturated brine, and the solvent was distilled off under reduced pressure. Thus obtained solid was purified by silica gel column chromatography (eluent:hexane:ethyl acetate=4:1) to give 0.36 g (yield 70%) of the title compound as a white solid.



1H-NMR (CDCl3, ppm) δ 7.76-7.82 (2H, m), 8.06 (1H, s), 8.29 (1H, s), 8.33-8.35 (1H, m), 8.49-8.53 (1H, m), 8.81 (1H, s).


Example 14-8
Preparation of N-(2,6-dibromo-4-heptafluoro-n-propylsulfinyl)phenyl 3-aminobenzamide (Compound No. I-57)

The title compound was obtained using N-(2,6-dibromo-4-heptafluoro-n-propylsulfinyl)phenyl 3-nitrobenzamide according to the conditions described in Example 1-2.



1H-NMR (CDCl3, ppm) δ 6.90-6.94 (1H, m), 7.28-7.33 (3H, m), 7.73 (1H, s), 8.02 (1H, s), 8.25 (1H, s).


Example 14-9
Preparation of N-(2,6-dibromo-4-heptafluoro-n-propylsulfinyl)phenyl 3-(benzoylamino)benzamide (Compound No. 335)

The title compound was obtained using N-(2,6-dibromo-4-heptafluoro-n-propylsulfinyl)phenyl 3-aminobenzamide according to the conditions described in Example 1-3.



1H-NMR (CDCl3, ppm) δ7.45-7.61 (4H, m), 7.77-7.79 (1H, m), 7.87-7.91 (3H, m), 8.01 (1H, s), 8.07-8.10 (1H, m), 8.15 (1H, s), 8.25 (1H, s), 8.38 (1H, s).


Example 14-10
Preparation of 2,6-dimethyl-4-(heptafluoro-n-propylthio)aniline

A mixture of 3.0 g (1.3 mmol) of 2,6-dibromo-4-heptafluoro-n-propylthioaniline, 3.0 g (21.9 mmol) of potassium carbonate, 0.75 g (0.65 mmol) of tetrakis(triphenylphosphine)palladium and 0.17 g (1.3 mmol) of trimethylboroxine was added to 20 ml of DMF, and this was stirred at 135° C. for 6 hours. The reaction solution was returned to room temperature, the insolubles were removed by celite filtration, and filtrate was concentrated under reduced pressure. Thus obtained residue was purified by silica gel column chromatography (eluent:hexane:ethyl acetate=12:1 to 4:1) to give 1.17 g (yield SS %) of the title compound as an oil.



1H-NMR (CDCl3, ppm) δ 2.17 (6H, s), 3.86 (2H, broad-s), 7.22 (2H, s).


Example 15
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(methylamino)benzamide

A mixture of 20.0 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide, 4.40 g of an aqueous solution of 37% formaldehyde, 2.0 g of 10% palladium-carbon and 200 ml of ethyl acetate was stirred under a hydrogen atmosphere at room temperature and ambient pressure. The insolubles in the reaction solution were separated by filtration, and the filtered residue was washed with ethyl acetated. The filtrate was collected, the solvent was distilled off under reduced pressure, and thus obtained residue was washed with diisopropyl ether to give 13.5 g (yield 65%) of the title compound as a white solid.



1H-NMR (CDCl3, ppm) δ 2.35 (6H, s), 2.91 (3H, s), 6.82 (1H, d, J=7.3 Hz), 7.18-7.52 (7H, m).


Example 16-1
Preparation of 3-(benzoylamino)benzoic Acid

To a solution of 1.37 g of 3-aminobenzoic acid and 0.4 g of sodium hydroxide in 50 ml of water, 1.41 g of benzoyl chloride and a solution containing 0.4 g of sodium hydroxide in 5 ml of water were simultaneously added dropwise, in an ice bath, and the mixture was stirred at room temperature for 6 hours. The reaction solution was adjusted to pH 1 by addition of 1N hydrochloric acid, and thus obtained solid was collected by filtration to give 1.92 g (yield 80%) of the title compound as a white solid.



1H-NMR (CDCl3, ppm) δ 7.40-7.56 (5H, m), 7.78 (1H, d, J=7.8 Hz), 8.00 (2H, d, J=8.3 Hz), 8.15 (1H, d, J=7.8 Hz), 8.35 (1H, t, J=2.0 Hz), 9.89 (1H, s).


Example 16-2
Preparation of 3-(benzoylamino)benzoyl Chloride

To a suspension of 1.5 g of 3-(benzoylamino)benzoic acid in 10 ml of toluene, 2 ml of thionyl chloride was added, and the mixture was stirred under reflux conditions for 2 hours. After the mixture was returned to room temperature, the solvent was distilled off under reduced pressure to give 1.53 g (yield 95%) of the title compound as a white solid.



1H-NMR (CDCl3, ppm) δ 7.51-7.62 (4H, m), 7.90 (2H, d, J=7.3 Hz), 7.93 (1H, s), 7.97 (1H, s), 8.15 (1H, dt, J=1.0, 5.9 Hz), 8.28 (1H, t, J=2.0 Hz).


Using readily available benzoic acids, the following compounds can be prepared according to the processes described in Examples 16-1 and 16-2:

  • 3-[(2-fluorobenzoyl)amino]benzoyl chloride
  • 3-[(3-fluorobenzoyl)amino]benzoyl chloride
  • 3-[(4-fluorobenzoyl)amino]benzoyl chloride
  • 3-[(2-chlorobenzoyl)amino]benzoyl chloride
  • 3-[(3-chlorobenzoyl)amino]benzoyl chloride
  • 3-[(4-chlorobenzoyl)amino]benzoyl chloride
  • 3-[(3-cyanobenzoyl)amino]benzoyl chloride
  • 3-[(4-cyanobenzoyl)amino]benzoyl chloride
  • 3-[(2-methyl benzoyl)amino]benzoyl chloride
  • 3-[(3-methyl benzoyl)amino]benzoyl chloride
  • 3-[(4-methyl benzoyl)amino]benzoyl chloride
  • 3-[(2-nitro benzoyl)amino]benzoyl chloride
  • 3-[(3-nitrobenzoyl)amino]benzoyl chloride
  • 3-[(4-nitrobenzoyl)amino]benzoyl chloride
  • 3-[(2-trifluoromethyl benzoyl)amino]benzoyl chloride
  • 3-[(3-trifluoromethyl benzoyl)amino]benzoyl chloride
  • 3-[(4-trifluoromethyl benzoyl)amino]benzoyl chloride
  • 3-[(2-trifluoromethoxy benzoyl)amino]benzoyl chloride
  • 3-[(3-trifluoromethoxy benzoyl)amino]benzoyl chloride
  • 3-[(4-trifluoromethoxy benzoyl)amino]benzoyl chloride
  • 3-[(2,3-difluorobenzoyl)amino]benzoyl chloride
  • 3-[(2,4-difluorobenzoyl)amino]benzoyl chloride
  • 3-[(2,5-difluorobenzoyl)amino]benzoyl chloride
  • 3-[(2,6-difluorobenzoyl)amino]benzoyl chloride
  • 3-[(3,4-difluorobenzoyl)amino]benzoyl chloride
  • 3-[(pyridin-3-yl)carbonylamino]benzoyl chloride
  • 3-[(2-fluoropyridin-3-yl)carbonylamino]benzoyl chloride
  • 3-[(2-chloropyridin-3-yl)carbonylamino]benzoyl chloride
  • 3-[(2, 4-dichlorobenzoyl)amino]benzoyl chloride
  • 3-[(2, 6-dichlorobenzoyl)amino]benzoyl chloride
  • 3-[(3,4-dichlorobenzoyl)amino]benzoyl chloride
  • 3-[(2-chloro-4-fluorobenzoyl)amino]benzoyl chloride
  • 3-[(4-chloro-2-fluorobenzoyl)amino]benzoyl chloride
  • 3-[(2-chloro-6-fluorobenzoyl)amino]benzoyl chloride
  • 3-[(2,3,6-trifluorobenzoyl)amino]benzoyl chloride


Example 16-3
Preparation of N-(2,6-dimethyl-4-heptafluoro-n-propylthio)phenyl 3-(benzoylamino)benzamide (Compound No. 260)

To a solution prepared by adding 0.1 g of 2,6-dimethyl-4-(heptafluoro-n-propylthio)aniline and 0.03 g of pyridine to 5 ml of tetrahydrofuran and stirring at room temperature, 0.09 g of 3-(benzoylamino)benzoyl chloride dissolved in 1 ml of tetrahydrofuran was introduced. After the mixture was stirred at room temperature for 1 hour, ethyl acetate and 1N hydrochloric acid were added, and the organic layer was separated. The organic layer was washed once with a saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate. This solution was filtered, the filtrate was collected, and the solvent was distilled off under reduced pressure. Thus obtained residue was purified by silica gel column chromatography (eluent:hexane:ethyl acetate=3:1) to give 0.10 g (yield 53%) of the title compound as a white solid.



1H-NMR (DMSO-d6, ppm) δ2.31 (6H, s), 7.41 (2H, s), 7.50-7.67 (5H, m), 7.71 (1H, d, J=7.8 Hz), 7.87-7.90 (3H, m), 8.07 (1H, s), 8.31 (1H, s).


Example 17-1
Preparation of 2,6-dimethyl-4-[1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl)eth yl]aniline

At room temperature, 24.4 g of 2,6-dimethylaniline and 50.0 g of hexafluoroacetone hydrate were mixed, and 0.5 g of p-toluenesulfonic acid monohydrate was added. The reaction solution was stirred and heated to 100° C. After the loss of the starting material was confirmed through TLC, ethyl acetate and an aqueous solution of 1N sodium hydroxide were added to the reaction solution, and phase separation was carried out. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was washed by addition of hexane. The suspension was filtered, and thus obtained filtered residue was dried under reduced pressure at room temperature to give 24.3 g (yield 69%) of the title compound as a powder form.



1H-NMR (CDCl3, ppm) δ2.20 (6H, s), 3.26 (1H, broad-s), 3.76 (2H, broad-s), 7.25 (2H, s).


Example 17-2
Preparation of N-[2,6-dimethyl-4-{1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl) ethyl}phenyl] 3-nitrobenzamide (Compound No. 1-124)

At room temperature, 5.0 g of 2,6-dimethyl-4-[1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl)eth yl]aniline, 3.9 g of 3-nitrobenzoyl chloride and 2.1 g of pyridine were introduced to 50 ml of tetrahydrofuran in a reactor, and the mixture was stirred at room temperature. After the loss of the starting material was confirmed through TLC, a saturated sodium hydrogen carbonate solution was added to the reaction solution and the solution was stirred for a while. Subsequently, ethyl acetate and water were added to the reaction solution, and phase separation was carried out. The separated organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and dried, and thus obtained residue was grinded to give 7.5 g (yield 95%) of the title compound as a powder form.



1H-NMR (DMSO-d6, ppm) δ 2.26 (6H, s), 7.46 (2H, s), 7.88 (1H, t, J=7.8 Hz), 8.43-8.48 (2H, m), 8.73 (1H, s), 8.81 (1H, s), 10.27 (1H, s).


Example 17-3
Preparation of N-[2,6-dimethyl-4-{1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl) ethyl}phenyl] 3-aminobenzamide (Compound No. 1-204)

A solution prepared by adding 8.0 g of N-[2,6-dimethyl-4-{1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl) ethyl}phenyl] 3-aminobenzamide and 0.8 g of 10% palladium-carbon to 50 ml of methanol, was stirred at room temperature under a hydrogen atmosphere. After the loss of the starting material was confirmed through TLC, the reaction solution filtered, and thus obtained filtrate was concentrated under reduced pressure. Thus obtained residue was purified by silica gel chromatography (eluent:hexane:ethyl acetate=3:1) to give 6.3 g (yield 85%) of the title compound as a powder form.



1H-NMR (DMSO-d6, ppm) δ2.35 (6H, s), 4.31 (2H, broad), 6.84-6.87 (1H, m), 7.21-7.25 (1H, m), 7.29-7.31 (2H, m), 7.47-7.49 (2H, m), 7.83 (1H, s), 8.94 (1H, s).


Example 17-4
Preparation of N-[2,6-dimethyl-4-{1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl) ethyl}phenyl] 3-(benzoylamino)benzamide (Compound No. 1-351)

At room temperature, 6.0 g of N-[2,6-dimethyl-4-{1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl) ethyl}phenyl] 3-aminobenzamide, 2.5 g of benzoyl chloride and 1.8 g of pyridine were introduced to 50 ml of tetrahydrofuran. After the loss of the starting material was confirmed through TLC, the reaction solution was filtered, and thus obtained filtrate was concentrated under reduce pressure. Thus obtained residue was purified by silica gel chromatography (eluent:hexane:ethyl acetate=3:1) to give 6.3 g (yield 85%) of the title compound as a powder form.



1H-NMR (DMSO-d6, ppm) δ 2.26 (6H, s), 7.44 (2H, s), 7.51-7.63 (4H, m), 7.74 (1H, d, J=7.8 Hz), 7.98-8.07 (3H, m), 8.35 (1H, s), 8.71 (1H, s), 9.90 (1H, s), 10.47 (1H, s).


Using 2-fluorobenzoyl chloride instead of benzoyl chloride, N-[2,6-dimethyl-4-{1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl) ethyl}phenyl] 3-[(2-fluorobenzoyl)amino]benzamide (Compound No. 1-358) was prepared according to Example 17-4.



1H-NMR (DMSO-d6, ppm) δ 2.34 (6H, s), 7.21 (1H, dd, J=8.2, 11.2 Hz), 7.32 (1H, t, J=7.8 Hz), 7.49-7.56 (4H, m), 7.78 (1H, d, J=7.8 Hz), 8.04-8.08 (2H, m), 8.23 (1H, s), 8.71 (1H, s), 9.08 (1H, d, J=11.2 Hz).


Example 17-5
Preparation of N-[2,6-dimethyl-4-{1-chloro-2,2,2-trifluoro-1-(trifluoromethyl)e thyl}phenyl] 3-(benzoylamino)benzamide (Compound No. 1-419)

At room temperature, 8.0 g of N-[2,6-dimethyl-4-{1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl) ethyl}phenyl] 3-(benzoylamino)benzamide and 1.0 g of pyridine were introduced to 40 ml of thionyl chloride. Then, the temperature was elevated, and the mixture was stirred under reflux conditions. After the loss of the starting material was confirmed through TLC, the reaction solution was cooled and was concentrated under reduce pressure. Thus obtained residue was purified by silica gel chromatography (eluent:hexane:ethyl acetate=3:1) to give 6.2 g (yield 75%) of the title compound as a powder form.



1H-NMR (DMSO-d6, ppm) δ 2.34 (6H, s), 7.49-7.63 (6H, m), 7.76 (1H, d, J=7.8 Hz), 7.99-8.08 (3H, m), 8.37 (1H, s), 9.99 (1H, s), 10.48 (1H, s).


Example 17-6
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(benzoylamino)benzamide (Compound No. 10)

At room temperature, 300 mg of N-[2,6-dimethyl-4-{1-chloro-2,2,2-trifluoro-1-(trifluoromethyl)e thyl}phenyl] 3-(benzoylamino)benzamide and 165 mg of potassium fluoride were introduced to 20 ml of N,N-dimethyl formamide. Then, the temperature was elevated to 120° C., and the mixture was stirred for 4 hours. The reaction solution was cooled to room temperature, ethyl acetate and water were added, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduce pressure. Thus obtained residue was washed by addition of diisopropyl ether. The suspension was filtered, and thus obtained filtered residue was dried under reduced pressure at room temperature to give 250 mg (yield 85%) of the title compound as a powder form.


The characterization is described in Example 1-3.


Example 17-7
N-[2,6-dimethyl-4-{1-hydroxy-2,2,2-trifluoro-1-(trifluorome thyl)ethyl}phenyl] 3-(benzoylamino)benzamide (Compound No. 1-351)

At room temperature, 2.0 g of 2,6-dimethyl-4-[1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl)eth yl]aniline, 2.7 g of 3-(benzoylamino)benzoyl chloride and 1.2 g of pyridine were introduced to 50 ml of tetrahydrofuran, and the mixture was stirred at room temperature. After the loss of the starting material was confirmed through TLC, a saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution and the solution was stirred for a while. Subsequently, ethyl acetate and water were added to the reaction solution, and phase separation was carried out. The separated organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and dried, and thus obtained residue was grinded to give 3.4 g (yield 95%) of the title compound as a powder form.


The characterization is described in Example 17-4.


Example 17-8
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(benzoylamino)benzamide (Compound No. 10)

At room temperature, 300 mg of N-[2,6-dimethyl-4-{1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl) ethyl}phenyl] 3-(benzoylamino)benzamide was introduced to 20 ml of methylene chloride. Then, 480 mg of 2,2-difluoro-1,3-dimethyl-2-imidazolidinone was added dropwise, and the mixture was stirred at room temperature for 8 hours. Water was added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate and filtered, and thus obtained filtrate was concentrated under reduce pressure and dried. Thus obtained solid was grinded to give 180 mg (yield 60%) of the title compound as a powder form.


The characterization is described in Example 1-3.


Example 18-1
Preparation of 4-methyl-5-nitro-2-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyri dine

After 1.33 g of 60% sodium hydride was introduced to 15 ml of tetrahydrofuran and cooled to 5° C., 5.84 g of 1,1,1,3,3,3-hexafluoro-2-propanol was added dropwise. The mixture was stirred at 5° C. for 30 minutes, and then 3.0 g of 2-chloro-4-methyl-5-nitropyridine dissolved in 10 ml of tetrahydrofuran was added dropwise, this being stirred at room temperature for 3 hours. After being left at room temperature for 3 days, ethyl acetate and water were added thereto, and the organic layer was separated and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Thus obtained residue was purified by silica gel column chromatography (eluent:hexane:ethyl acetate=10:1) to give 4.5 g (yield 80%) of the title compound as a yellow oil.



1H-NMR (CDCl3, ppm) δ 2.69 (3H, s), 6.54 (1H, septet, J=6.8 Hz), 6.95 (1H, s), 8.90 (1H, s).


Example 18-2
Preparation of 5-amino-4-methyl-2-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyri dine

The title compound was prepared using 4-methyl-5-nitro-2-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyri dine according to the conditions described in Example 1-2.



1H-NMR (CDCl3, ppm) δ2.04 (3H, s), 3.49 (2H, broad-s), 6.40 (1H, septet, J=6.3 Hz), 6.69 (1H, s), 7.54 (1H, s).


Example 18-3
Preparation of 3-amino-2-chloro-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethylet hoxy)pyridine

1.0 g of 5-amino-4-methyl-2-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyri dine was introduced to 10 ml of N,N-dimethyl formamide, and 0.56 g of N-chlorosuccinimide was added at room temperature. The temperature was elevated to 60° C., and the mixture was stirred for 1 hour and poured into water. The mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and thus obtained residue was purified by silica gel column chromatography (eluent:hexane:ethyl acetate=10:1) to give 0.50 g (yield 44%) of the title compound as a brown oil.



1H-NMR (CDCl3, ppm) δ 2.23 (3H, s), 3.82 (2H, broad-s), 6.24 (1H, septet, J=6.3 Hz), 6.67 (1H, s).


Example 18-4
Preparation of N-[2-chloro-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy) pyridin-3-yl] 3-(benzoylamino)benzamide (Compound No. 464)

The title compound was prepared using 5-amino-4-methyl-2-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyri dine according to the conditions described in Example 1.



1H-NMR (CDCl3, ppm) δ 2.38 (3H, s), 6.34 (1H, septet, J=6.3 Hz), 6.87 (1H, s), 7.50-7.63 (5H, m), 7.72 (1H, d, J=7.8 Hz), 7.88-7.90 (3H, m), 7.99 (1H, broad-s), 8.31 (1H, broad-s).


Preparation examples containing the compound represented by Formula (1) of the invention as an active ingredient are presented in the following, but the invention is not intended to be limited thereto. Additionally, in the formulations, the unit expressed in parts mean parts by weight.


Preparation Example 1

An emulsion was obtained by homogeneously mixing, with stirring, 20 parts of the compound represented by Formula (1) of the invention, 10 parts of Sol Pol 355S (Toho Chemical Industry Co., LTD, a surfactant) and 70 parts of xylene.


Preparation Example 2

A water-dispersible powder was obtained by homogeneously mixing, with stirring, 10 parts of the compound represented by Formula (1) of the invention, 2 parts of sodium alkylnaphthalenesulfonate, 1 part of sodium ligninsulfonate, 5 parts of white carbon and 82 parts of diatomite.


Preparation Example 3

A dust formulation was obtained by homogeneously mixing, with grinding, a homogeneous mixture of 0.3 part of the compound represented by Formula (1) of the invention and 0.3 part of white carbon with 99.2 parts of clay and 0.2 part of Driless A (Sankyo Co., Ltd).


Preparation Example 4

A granule was obtained by homogeneously mixing, with grinding, 2 parts of the compound represented by Formula (1) of the invention, 2 parts of white carbon, 2 parts of sodium ligninsulfonate and 94 parts of bentonite, kneading with water, and by granulating and drying.


Preparation Example 5

A flowable formulation was prepared by sufficiently stirring and mixing 20 parts of the compound represented by Formula (1) of the invention and 5 parts of a 20% aqueous solution of polyvinyl alcohol, adding 75 parts of a 0.8% aqueous solution of xanthan gum, and stirring and mixing them again.


Furthermore, in order to confirm the excellent insecticidal activity of the compound represented by Formula (1) of the invention, Experimental Examples will be presented below, which are not intended to limit the invention anyway.


Experimental Example 1

Insecticidal testing against common cutworm (Spodoptera litura)


Cabbage leaves were immersed in a liquid comprising the testing compound to a predetermined concentration for 30 seconds and air-dried. They were placed in a 7-cm polyethylene cup, and the second-stage larvae of common cutworm were left therein. The cup was placed in a constant-temperature room at 25° C., and the survival rate was investigated after 3 days. The test was carried out with two groups of 5 larvae per group. As a result, Compound No. (to be described later) 2,3,4,5,6,7,8,9,10,11,12,13,14,16,17,18,19,20,21,22,23,25,26,27, 28,29,30,31,32,33,37,39,42,43,46,48,56,57,58,59,60,61,62,66,68, 69,70,71,73,74,75,81,82,83,84,85,86,87,89,92,96,99,100,101,105, 106,109,114,117,122,124,125,126,127,129,130,132,136,140,150,160, 163,164,165,166,168,169,170,171,172,173,174,175,176,177,178,179, 180,181,182,183,184,185,186,187,188,189,190,191,192,193,194,195, 196,197,198,199,200,201,202,204,207,208,210,212,256,257,258,259, 260,261,262,263,266,276,284,288,309,310,327,328,329,330,331,332, 333,334,335,338,369,375,376,377,378,379,380,383,414,460,461,462, 463,464,465,466,467,601,602,603,604,605,606,607,609,610,611,612, 616,618,619,624,628,629,630,631,633,634,638,639,649,650,651,652, 653,654,655,656,657,658,661,665,668,670,676,679,682,686,699,708, 711,719,722,791,1001,1016,1043,1089,1091,1097,1100,1125,1126, 1206,1207,1208,1209,1210,1211,1212,1213,1214,1216,1217,1218, 1219,1220,1229,1235,1236,1237,1238,1245,1246,1247,1255,1256, 1257,1258,1259,1260,1261,1262,1263,1264,1265,1266,1267,1274, 1293,1294,1463,1464,1465,1478,1479,1480,1481,1482,1483,1484, 1485,1486,1487,1607,1617,1645,1697,2001,2004,2034,2035,2036, 2037,2082,2085,2093,2116,2117,2164,2168,2201,2202,2203 exhibited an pesticidal rate of 70% or more at a concentration of 100 ppm.


Experimental Example 2

Insecticidal testing against diamondback moth (Plutella xylostella)


Cabbage leaves were immersed in a liquid comprising the testing compound to a predetermined concentration for 30 seconds and air-dried. They were placed in a 7-cm polyethylene cup, and the second-stage larvae of diamondback moth were left therein. The cup was placed in a constant-temperature room at 25° C., and the survival rate was investigated after 3 days. The test was carried out with two groups of 5 larvae per group. As a result, Compound No. (to be described later) 2,3,4,5,6,7,8,9,10,11,12,13,17,18,19,20,21,22,23,25,26,27,29,30, 31,32,33,37,39,43,47,56,58,59,60,61,62,66,68,69,70,82,83,84,85, 86,87,89,92,100,101,105,106,109,114,118,122,124,127,130,132,135, 147,150,154,160,163,164,165,166,168,169,170,171,172,173,174,175, 176,177,178,179,180,181,182,183,184,185,186,194,196,197,198,199, 200,201,202,203,204,206,207,208,209,210,212,256,258,259,260,261, 262,263,266,284,309,310,314,318,327,328,329,330,331,332,333,334, 335,338,369,375,376,377,378,379,383,414,460,461,462,463,464,465, 466,467,601,602,603,604,605,606,607,609,610,611,612,616,618,619, 620,624,628,629,630,631,633,634,638,639,650,651,652,653,654,655, 656,657,665,668,670,676,679,682,686,699,708,711,719,722,791, 1001,1016,1043,1089,1091,1097,1100,1125,1126,1206,1207,1208, 1209,1210,1211,1212,1213,1214,1215,1216,1217,1218,1219,1220, 1229,1235,1236,1237,1238,1245,1246,1247,1255,1256,1257,1258, 1259,1260,1261,1262,1263,1264,1265,1266,1267,1274,1293,1294, 1463,1464,1465,1478,1479,1480,1481,1482,1484,1485,1486,1487, 1607,1617,1645,1697,2001,2034,2037,2082,2085,2093,2116,2117, 2164,2168,2201,2202,2203 exhibited an pesticidal rate of 70% or more at a concentration of 100 ppm.


Experimental Example 3

Insecticidal Testing Against Small Brown Planthopper (Laodelphax striatellus)


An additional test was carried out with 10 small brown planthoppers by preparing an acetone solution of the testing compound diluted to a predetermined concentration, and spraying the solution on rice paddies and air drying them. The medicament was all used as received. The paddies were placed in a constant-temperature room at 25° C., and the survival rate was investigated after 6 days. The test was carried out by means of one group of 10 pests. As a result, Compound No. (to be described later) 7,8,17,25,31,62,101,105,106,122,130,164,165,166,169,170,171,172, 173,174,175,178,179,180,181,182,183,184,185,197,199,201,202,206, 207,208,210,369,601,604,607,609,610,611,612,618,619,620,624,628, 630,633,639,650,651,652,654,655,657,665,668,686,1043,1089,1091, 1097,1100,1207,1208,1209,1210,1211,1212,1213,1214,1216,1217, 1218,1219,1220,1229,1235,1236,1237,1238,1245,1246,1247,1255, 1259,1260,1262,1263,1264,1265,1266,1293,1463,1464,1465,1487, 1607,1645,1697,2034,2035,2082,2085,2093,2116,2117,2203 exhibited an pesticidal rate of 70% or more at a concentration of 1000 ppm.


Comparative Experimental Example 1

Pesticidal testing using N-(4-heptafluoroisopropyl-2-methyl)phenyl 3-(2-iodobenzoylamino)benzamide (Compound A) and N-(2,6-dimethyl-4-trifluoromethyl)phenyl 3-(benzoylamino)benzamide (Compound B)


Additional tests were carried out using said Compound A and Compound B following the procedures of Experimental Examples 1 and 2, but insecticidal activity was not observed under the same conditions.

Claims
  • 1-14. (canceled)
  • 15. A compound represented by Formula (8):
  • 16. A compound represented by Formula (11):
  • 17. A compound represented by Formula (13):
Priority Claims (3)
Number Date Country Kind
2004-019438 Jan 2004 JP national
2004-048031 Feb 2004 JP national
2004-209002 Jul 2004 JP national
Divisions (6)
Number Date Country
Parent 15871552 Jan 2018 US
Child 16552032 US
Parent 14854627 Sep 2015 US
Child 15871552 US
Parent 14220673 Mar 2014 US
Child 14854627 US
Parent 14033005 Sep 2013 US
Child 14220673 US
Parent 13427176 Mar 2012 US
Child 14033005 US
Parent 10587990 Jun 2007 US
Child 13427176 US