Insecticidal and fungicidal composition

TECHNICAL FIELD

The present invention relates to a novel insecticidal and fungicidal composition exhibiting excellent insecticidal and fungicidal actions for the labor-saving control of crop diseases and insect pests.

BACKGROUND ART

The compound represented by the general formula (1) of the present invention is a novel compound having an insecticidal activity.

In International Publication No. 2000/55120 pamphlet and U.S. Pat. No. 6,548,514, a compound similar to the compound represented by the general formula (1) of the present invention for medical use is described. But activity against insects is never described therein. Furthermore, it is obvious that such compounds are not included in the claims of the present invention.

In International Publication No. 2000/7980 pamphlet, a compound similar to the compound represented by the general formula (1) of the present invention for medical use is described. But activity against insects is never described therein. Furthermore, it is obvious that such a compound is not included in the claims of the present invention.

In US Patent Laid-Open No. 2002-032238, a compound similar to the compound represented by the general formula (1) of the present invention for medical use is described. But activity against insects is never described therein. Furthermore, it is obvious that such a compound is not included in the claims of the present invention.

Meanwhile, the compound represented by the general formula (2) is described in International Publication No. 2005/21488 pamphlet before the application of the present invention and the compound itself has an insecticidal action. In addition, in International Publication No. 2003/008372 pamphlet and International Publication No. 2005/042474 pamphlet, it has been described that the compound represented by the general formula (3) or (4) has a control action against rice blast (Pyricularia oryzae)

However, these active compounds have an action exhibiting any of an insecticidal effect or a fungicidal effect with the use of a single agent thereof, but cannot control crop diseases and insect pests at the same time.

Patent Document 1: International Publication No. 2000/55120 pamphlet

Patent Document 2: U.S. Pat. No. 6,548,514

Patent Document 3: International Publication No. 2000/7980 pamphlet

Patent Document 4: US Patent Laid-Open No. 2002-032238

Patent Document 5: International Publication No. 2005/21488 pamphlet

Patent Document 6: International Publication No. 2003/8372 pamphlet

Patent Document 7: International Publication No. 2005/42474 pamphlet

DISCLOSURE OF THE INVENTION

The present invention is to provide an insecticidal and fungicidal composition capable of controlling crop diseases and insect pests at the same time by combining an insecticidal active ingredient and a fungicidal active ingredient.

In order to solve the aforementioned object, the present inventors have repeatedly conducted an extensive study and as a result, have found that an insecticidal and fungicidal composition containing one or more compounds represented by the general formula (1) or (2) as insecticidal active ingredients, and one or more compounds represented by the general formula (3) or (4) as fungicidal active ingredients has excellent insecticidal and fungicidal effects on crop diseases and insect pests. Thus, the present invention has been completed.

That is, the present invention is specified by the following matters:

[1] an insecticidal and fungicidal composition comprising;

one or two or more compounds selected from compounds represented by the general formula (1) or (2); and

one or two or more compounds selected from compounds represented by the general formula (3) or (4) as active ingredients,

wherein, in the formula (1), X₁is a hydrogen atom or a fluorine atom; R₁and R₂are independently a hydrogen atom or a C1-C4 alkyl group; Q₁is a phenyl group,

a substituted phenyl group having one or more substituents which may be the same or different and are 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 hydroxy 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 pyridyl group having one or more substituents which may be the same or different and are 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 hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 alkylcarbonyloxy group, a C1-C4 alkoxycarbonyl group, an acetylamino group and a phenyl group; and

Q₂is represented by the general formula (A),

wherein, in the formula (A), Y₁and Y₅may be the same or different and represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 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 or a cyano group; Y₃represents a C2-C6 perfluoroalkyl group, a C2-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y₂and Y₄represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group, or

wherein, in the formula (2), X₂is a hydrogen atom or a fluorine atom; R₄and R₅are independently a hydrogen atom or a C1-C4 alkyl group; R₃represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group,

-E₁-Z₁-R₆(wherein, in the formula, E₁represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group or a C3-C4 haloalkynylene group; R₆represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group or a C2-C6 haloalkynyl group; Z₁represents —O—, —S—, —SO—, —SO₂—, —C(═O)—, —C(═O)O—, —OC(═O)—, —N(R₇)—, —C(═O)N(R₇)— or —N(R₇)C(═O)— (R₇represents a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group or a C1-C4 alkoxycarbonyl group)) or

-E₂-R₈(wherein, in the formula, E₂represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group or a C3-C4 haloalkynylene group; R₈represents a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a cyano group, a nitro group, a hydroxy group, a phenyl group,

a substituted phenyl group having one or more substituents which may be the same or different and are selected from a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl 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 cyano group, a nitro group, a hydroxy group, a C1-C4 alkylcarbonyl group, a C1-C4 haloalkylcarbonyl group, a C1-C4 alkylcarbonyloxy group and a C1-C4 alkoxycarbonyl group,

a pyridyl group,

a substituted pyridyl group having one or more substituents selected from a halogen atom, a C1-C6 haloalkyl group and a C1-C6 haloalkoxy group,

a thienyl group, or

a tetrahydrofuran group); and

Q₃represents the general formula (B),

wherein, in the formula (B), Y₆and Y₁₀may be the same or different and represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkoxy group, a C1-C4 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 or a cyano group; Y₈represents a C2-C6 perfluoroalkyl group, a C1-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y₇and Y₉represent a hydrogen atom, a halogen atom or a C1-C4 alkyl group, and

wherein, in the formula (3), R11 represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an arylalkyl group or a heterocyclic alkyl group; R₁₂and R₁₇independently represent a hydrogen atom; R₁₃and R₁₄each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R₁₅and R₁₆independently represent a hydrogen atom; and R₁₈represents an aryl group or a heterocycle, or

wherein, in the formula (4), R₂₁represents an alkyl group having 1 to 6 carbon atoms substituted with halogen, a cycloalkyl group having 3 to 6 carbon atoms substituted with halogen or an alkenyl group having 2 to 6 carbon atoms substituted with halogen; R₂₂and R₂₇independently represent a hydrogen atom; R₂₃and R₂₄each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R₂₅and R₂₆independently represent a hydrogen atom; and R₂₈represents an aryl group or a heterocycle;

[2] an insecticidal and fungicidal composition containing one or two or more compounds selected from compounds represented by the general formula (1) as set forth in [1] and one or two or more compounds selected from compounds represented by the general formula (3) as set forth in [1] as active ingredients;

[3] an insecticidal and fungicidal composition containing one or two or more compounds selected from compounds represented by the general formula (1) as set forth in [1] and one or two or more compounds selected from compounds represented by the general formula (4) as set forth in [1] as active ingredients;

[4] an insecticidal and fungicidal composition containing one or two or more compounds selected from compounds represented by the general formula (2) as set forth in [1] and one or two or more compounds selected from compounds represented by the general formula (3) as set forth in [1] as active ingredients; and

[5] an insecticidal and fungicidal composition containing one or two or more compounds selected from compounds represented by the general formula (2) as set forth in [1] and one or two or more compounds selected from compounds represented by the general formula (4) as set forth in [1] as active ingredients.

The nursery box treatment of paddy rice using the insecticidal and fungicidal composition of the present invention is helpful in decreasing the amount of a liquid chemical per unit area and reducing the influence on the environment as well as in reducing burden of a farmhouse's labor. Furthermore, it is further helpful in saving much labor by mixing with a fertilizer and carrying out fertilizer application at the time of rice transplantation or setting. Accordingly, the insecticidal and fungicidal composition of the present invention is extremely effective in control of diseases and insect pests at the same time, and saving labor for agricultural products, and horticultural products, and provides technical inventiveness which is also excellent in industrial effectiveness.

Control of insect pests and control of diseases must be conducted with the use of a single active compound, but the insecticidal and fungicidal composition of the present invention is capable of the labor-saving control of diseases and insect pests at the same time.

BEST MODE FOR CARRYING OUT THE INVENTION

The present invention will be described in more detail below. Wordings used in general formulae (1) and the (2) of the present invention have the respective meanings as described hereinafter in terms of definitions.

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

In expression of “Ca-Cb (a and b represent an integer of not less than 1)”, for example, “C1-C3” refers to 1 to 3 carbon atoms, “C2-C6” refers to 2 to 6 carbon atoms, and “C1-C4” refers to 1 to 4 carbon atoms.

“n-” refers to normal, “i-” refers to iso, “s-” refers to secondary and “t-” refers to tertiary.

The “C1-C3 alkyl group” represents, for example, linear, branched or cyclic alkyl groups having 1 to 3 carbon atoms such as methyl, ethyl, n-propyl, i-propyl, cyclopropyl and the like. The “C1-C4 alkyl group” represents, for example, linear or branched alkyl groups having 1 to 4 carbon atoms such as n-butyl, s-butyl, i-butyl, t-butyl and the like, in addition to “C1-C3 alkyl group.” The “C1-C6 alkyl group” represents, for example, linear or branched alkyl groups 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 and the like, in addition to “C1-C4 alkyl group.”

The “C1-C3 haloalkyl group” represents, for example, linear or branched alkyl groups having 1 to 3 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as monofluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, 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-tribromoethyl, 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, heptafluoro-n-propyl and the like. The “C1-C4 haloalkyl group” represents, for example, linear or branched alkyl groups having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as 4-fluoro-n-butyl, nonafluoro-n-butyl, nonafluoro-2-butyl and the like, in addition to “C1-C3 haloalkyl group.” The “C1-C6 haloalkyl group” represents, for example, linear or branched alkyl groups having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different.

The “C2-C4 alkenyl group” represents, for example, alkenyl groups of 2 to 4 carbon atoms having a double bond in the carbon chain such as vinyl, allyl, 2-butenyl, 3-butenyl and the like, and the “C2-C6 alkenyl group” represents, for example, alkenyl groups of 2 to 6 carbon atoms having a double bond in the carbon chain. The “C2-C4 haloalkenyl group” represents, for example, linear or branched alkenyl groups of 2 to 4 carbon atoms having a double bond in the carbon atom substituted with one or more halogen atoms which may be the same or different, such as 3,3-difluoro-2-propenyl, 3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl, 2,3-dibromo-2-propenyl, 4,4-difluoro-3-butenyl, 3,4,4-tribromo-3-butenyl and the like, and the “C2-C6 haloalkenyl group” represents, for example, linear or branched alkenyl groups of 2 to 6 carbon atoms having a double bond in the carbon chain substituted with one or more halogen atoms which may be the same or different.

The “C2-C4 alkynyl group” represents, for example, linear or branched alkynyl groups of 2 to 4 carbon atoms having a triple bond in the carbon chain such as propargyl, 1-butyne-3-yl, 1-butyne-3-methyl-3-yl and the like, and the “C2-C6 alkynyl group” represents, for example, linear or branched alkynyl groups of 2 to 6 carbon atoms having a triple bond in the carbon chain. The “C2-C4 haloalkynyl group” represents, for example, linear or branched alkenyl groups of 2 to 4 carbon atoms having a triple bond in the carbon chain substituted with one or more halogen atoms which may be the same or different, the “C2-C6 haloalkynyl group” represents, for example, linear or branched alkenyl groups of 2 to 6 carbon atoms having a triple bond in the carbon chain substituted with one or more halogen atoms which may be the same or different.

The “C3-C6 cycloalkyl group” represents, for example, cycloalkyl groups of 3 to 6 carbon atoms having a cyclic structure, such as cyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl and the like, and the “C3-C8 cycloalkyl group” represents, for example, cycloalkyl groups of 3 to 8 carbon atoms having a cyclic structure. The “C3-C6 halocycloalkyl group” represents, for example, cycloalkyl groups of 3 to 6 carbon atoms having a cyclic structure substituted with one or more halogen atoms which may be the same or different, such as 2,2,3,3-tetrafluorocyclobutyl, 2-chlorocyclohexyl, 4-chlorocyclohexyl and the like, and the “C3-C8 halocycloalkyl group” represents, for example, cycloalkyl groups of 3 to 8 carbon atoms having a cyclic structure substituted with one or more halogen atoms which may be the same or different.

The “C1-C3 alkoxy group” represents, for example, linear or branched alkoxy groups having 1 to 3 carbon atoms such as methoxy, ethoxy, n-propyloxy, isopropyloxy and the like, and the “C1-C6 alkoxy group” represents linear or branched alkoxy groups having 1 to 6 carbon atoms. The “C1-C3 haloalkoxy group” represents, for example, linear or branched haloalkoxy groups having 1 to 3 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as trifluoromethoxy, 1,1,1,3,3,3-hexafluoro-2-propyloxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy, 3-fluoro-n-propyloxy and the like, the “C1-C4 haloalkoxy group” represents, for example, linear or branched haloalkoxy groups having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as 1,1,1,3,3,4,4,4-octafluoro-2-butyloxy and the like, in addition to “C1-C3 haloalkoxy group,” and the “C1-C6 haloalkoxy group” represents, for example, linear or branched haloalkoxy groups having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different.

The “C1-C3 alkylthio group” represents, for example, linear, branched or cyclic alkylthio groups having 1 to 3 carbon atoms such as methylthio, ethylthio, n-propylthio, i-propylthio, cyclopropylthio and the like, the “C1-C4 alkylthio group” represents, for example, linear, branched or cyclic alkylthio groups having 1 to 4 carbon atoms such as n-butylthio, i-butylthio, s-butylthio, t-butylthio, cyclopropylmethylthio and the like, in addition to “C1-C3 alkylthio group,” and the “C1-C6 alkylthio group” represents, for example, linear or branched alkylthio groups having 1 to 6 carbon atoms. The “C1-C3 haloalkylthio group” represents, for example, linear or branched alkylthio groups having 1 to 3 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, heptafluoro-n-propylthio, heptafluoro-i-propylthio and the like. The “C1-C4 haloalkylthio group” represents, for example, linear or branched alkylthio groups having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as nonafluoro-n-butylthio, nonafluoro-s-butylthio, 4,4,4-trifluoro-n-butylthio and the like, in addition to “C1-C3 haloalkylthio group,” and the “C1-C6 haloalkylthio group” represents, for example, linear or branched alkylthio groups having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different.

The “C1-C3 alkylsulfinyl group” represents, for example, linear, branched or cyclic alkylsulfinyl groups having 1 to 3 carbon atoms, such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, cyclopropylsulfinyl and the like, and the “C1-C6 alkylsulfinyl group” represents linear or branched alkylsulfinyl groups having 1 to 6 carbon atoms. The “C1-C3 haloalkylsulfinyl group” represents, for example, linear or branched alkylsulfinyl groups having 1 to 3 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as trifluoromethylsulfinyl, pentafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, heptafluoro-n-propylsulfinyl, heptafluoro-i-propylsulfinyl and the like, and the “C1-C6 haloalkylsulfinyl group” represents, for example, linear or branched alkylsulfinyl groups having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different.

The “C1-C3 alkylsulfonyl group” represents, for example, linear, branched or cyclic alkylsulfonyl groups having 1 to 3 carbon atoms, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, cyclopropylsulfonyl and the like, and the “C1-C6 alkylsulfonyl group” represents linear or branched alkylsulfonyl groups having 1 to 6 carbon atoms. The “C1-C3 haloalkylsulfonyl group” represents, for example, linear or branched alkylsulfonyl groups having 1 to 3 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as trifluoromethylsulfonyl, pentafluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, heptafluoro-n-propylsulfonyl, heptafluoro-i-propylsulfonyl and the like, and the “C1-C6 haloalkylsulfonyl group” represents, for example, linear or branched alkylsulfonyl groups having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different.

The “C1-C4 alkylamino group” represents, for example, linear, branched or cyclic alkylamino groups having 1 to 4 carbon atoms, such as methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino, cyclopropylamino and the like, and the “di C1-C4 alkylamino group” represents, for example, linear or branched amino groups substituted with two alkyl groups having 1 to 4 carbon atoms which may be the same or different, such as dimethylamino, diethylamino, N-ethyl-N-methylamino and the like.

The “C1-C4 alkylcarbonyl group” represents, for example, linear, branched or cyclic alkylcarbonyl groups having 1 to 4 carbon atoms, such as formyl, acetyl, propionyl, isopropylcarbonyl, cyclopropylcarbonyl and the like.

The “C1-C4 haloalkylcarbonyl group” include linear or branched alkylcarbonyl groups having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as fluoroacetyl, difluoroacetyl, trifluoroacetyl, chloroacetyl, dichloroacetyl, trichloroacetyl, bromoacetyl, iodoacetyl, 3,3,3-trifluoropropionyl, 2,2,3,3,3-pentafluoropropionyl and the like.

The “C1-C4 alkylcarbonyloxy group” represents, for example, linear or branched alkylcarbonyloxy groups having 1 to 4 carbon atoms, such as acetoxy, propionyloxy and the like.

The “C1-C4 alkoxycarbonyl group” represents, for example, linear or branched alkoxycarbonyl groups having 1 to 4 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, isopropyloxycarbonyl and the like.

The “C1-C4 perfluoroalkyl group” represents, for example, linear or branched alkyl groups having 1 to 4 carbon atoms which are all substituted with fluorine atoms, such as trifluoromethyl, pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-i-propyl, nonafluoro-n-butyl, nonafluoro-2-butyl, nonafluoro-i-butyl and the like, and the “C2-C6 perfluoroalkyl group” represents, for example, linear or branched alkyl groups having 2 to 6 carbon atoms which are all 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, perfluoro-n-hexyl and the like.

The “C1-C6 perfluoroalkylthio group” represents, for example, linear or branched alkylthio groups having 1 to 6 carbon atoms which are all 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, perfluoro-n-hexylthio and the like.

The “C1-C6 perfluoroalkylsulfinyl group” represents, for example, linear or branched alkylsulfinyl groups having 1 to 6 carbon atoms which are all 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, perfluoro-n-hexylsulfinyl and the like.

The “C1-C6 perfluoroalkylsulfonyl group” represents, for example, linear or branched alkylsulfonyl groups having 1 to 6 carbon atoms which are all 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, perfluoro-n-hexylsulfonyl and the like.

The “C1-C4 alkylene group” represents, for example, linear or branched alkylene groups having 1 to 4 carbon atoms such as methylene, ethylene, propylene, dimethylmethylene, isobutylene and the like. The “C2-C4 alkenylene group” represents, for example, linear or branched alkenylene groups of 2 to 4 carbon atoms having a double bond in the carbon atom. The “C3-C4 alkynylene group” represents, for example, linear or branched alkynylene groups of 3 to 4 carbon atoms having a triple bond in the carbon chain. The “C1-C4 haloalkylene group” represents, for example, linear or branched alkylene groups having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as chloromethylene, chloroethylene, dichloromethylene, difluoromethylene and the like. The “C2-C4 haloalkenylene group” represents, for example, linear or branched alkynylene groups of 2 to 4 carbon atoms having a double bond in the carbon chain substituted with one or more halogen atoms which may be the same or different. The “C3-C4 haloalkynylene group” represents, for example, linear or branched alkynylene groups of 3 to 4 carbon atoms having a triple bond in the carbon chain substituted with one or more halogen atoms which may be the same or different.

The compounds represented by the general formulae (1) and (2) of the present invention contain one or more asymmetric carbon atoms or asymmetric centers in its structural formula in some cases and have two or more optical isomers in some cases. However, the present invention also includes all of the respective optical isomers and mixtures consisting of these isomers in any ratio. Furthermore, the compounds represented by the general formulae (1) and (2) of the present invention have two or more geometrical isomers derived from a carbon-carbon double bond in its structural formula in some cases. However, the present invention also includes all of the respective geometrical isomers and mixtures consisting of these isomers in any ratio.

As the substituents in the compounds represented by the general formulae (1) and (2) of the present invention, preferable substituents or atoms are as follows.

R₁is preferably a hydrogen atom or a C1-C4 alkyl group and further preferably a hydrogen atom, a methyl group or an ethyl group.

R₂is preferably a hydrogen atom or a C1-C4 alkyl group, and further preferably a hydrogen atom, a methyl group or an ethyl group.

R₄is preferably a hydrogen atom or a C1-C4 alkyl group, and further preferably a hydrogen atom, a methyl group or an ethyl group.

R₅is preferably a hydrogen atom or a C1-C4 alkyl group, and further preferably a hydrogen atom, a methyl group or an ethyl group.

X₁is preferably a hydrogen atom or a fluorine atom.

X₂is preferably a hydrogen atom or a fluorine atom.

Q₁is preferably a phenyl group,

a pyridyl group, or

and further preferably a phenyl group,

a substituted phenyl group having one to three substituents which may be the same or different and are 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 one to two substituents which may be the same or different and are 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.

Q₂is preferably is a substituted phenyl group represented by the general formula (A). In the formula, Y₁and Y₅are preferably independently 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 pentafluoroethylthio group, a trifluoromethylsulfinyl group, a pentafluoroethylsulfinyl group, a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group or a cyano group; Y₂and Y₄are preferably a hydrogen atom, a halogen atom or a methyl group, and further preferably a hydrogen atom; and Y₃is 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 a nonafluoro-2-butylsulfonyl group. Q₃is preferably a substituted phenyl group represented by the general formula (B). In the formula, Y₆and Y₁₀are preferably independently 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 pentafluoroethylthio group, a trifluoromethylsulfinyl group, a pentafluoroethylsulfinyl group, a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group or a cyano group; Y₇and Y₉are preferably a hydrogen atom, a halogen atom or a methyl group, and further preferably a hydrogen atom; Y₈is 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 a nonafluoro-2-butylsulfonyl group; R₃is preferably a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, -E₁-Z₁-R₆(wherein, in the formula, E₁represents a C1-C4 alkylene group, a C2-C4 alkenylene group, a C3-C4 alkynylene group, a C1-C4 haloalkylene group, a C2-C4 haloalkenylene group or a C3-C4 haloalkynylene group; R₆represents a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group or a C2-C6 haloalkynyl group; and Z₁represents —O—, —S—, —SO— or —SO₂—), -E₂-R₈(wherein, in the formula, E₂represents a C1-C4 alkyl group, a C2-C4 alkenyl group, a C3-C4 alkynyl group, a C1-C4 haloalkyl group, a C2-C4 haloalkenyl group or a C3-C4 haloalkynyl group; and R₈represents a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, a cyano group, a nitro group, a hydroxy group, a phenyl group,

a pyridyl group, or

a substituted pyridyl group having one or more substituents selected from a halogen atom, a C1-C6 haloalkyl group and a C1-C6 haloalkoxy group); and R₃is more preferably a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C3-C8 halocycloalkyl group, -E₁-Z₁-R₆(wherein, in the formula, E₁represents a C1-C4 alkylene group or a C1-C4 haloalkylene group; R₆represents a C1-C6 alkyl group; and Z₁represents —O—, —S—, —SO—, —SO₂—), or -E₂-R₈(wherein, in the formula, E₂represents a C1-C4 alkyl group; and R₈represents a C3-C8 cycloalkyl group, a cyano group,

a substituted phenyl group having one or more substituents which may be the same or different and are selected from a halogen atom, a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, a C1-C6 haloalkylsulfonyl group, a cyano group and a nitro group,

a pyridyl group,

a substituted pyridyl group having one or more substituents selected from a halogen atom, a C1-C6 haloalkyl group and a C1-C6 haloalkoxy group,

a thienyl group, or

a tetrahydrofuran group).

In the compounds represented by the general formulae (3) and (4), typical examples of the substituent can be cited as follows, but the present invention is not restricted to the following substituents.

Examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group and the like.

Examples of the alkenyl group having 2 to 6 carbon atoms include a vinyl group, a propenyl group, a butenyl group, a pentenyl group, a hexenyl group and the like.

Examples of the alkyl group having 1 to 6 carbons substituted with halogen include chlorine substituted alkyl groups such as a chloromethyl group, a 2-chloroethyl group, a 2,2,2-trichloroethyl group, a 3-chloro-1-propyl group, a 4-chloro-1-butyl group and the like; fluorine substituted alkyl groups such as a 2-fluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,1,3,3,3-hexafluoro-2-propyl group, a 1,3-difluoro-2-propyl group, a 5-fluoro-1-pentyl group, a 6,6,6,5,5,4,4,3,3-nonafluoro-1-hexyl group, a 1-ethoxy-2,2,2-trifluoroethyl group and the like; bromine substituted alkyl groups such as a 2-bromoethyl group, a 1,3-dibromo-2-propyl group and the like; iodine substituted alkyl groups such as a 2-iodoethyl group and the like; and alkyl groups containing two or more halogens such as a 3-bromo-1,1,1-trifluoro-2-propyl group and the like.

Examples of the cycloalkyl group having 3 to 6 carbons substituted with halogen include chlorine substituted cycloalkyl groups such as a chlorocyclopropyl group, a 2-chlorocyclobutyl group, a 2-chlorocyclopentyl group, a 2-chlorocyclohexyl group, a 3-chlorocyclohexyl group, a 4-chlorocyclohexyl group and the like; fluorine substituted cycloalkyl groups such as a 2-fluorocyclohexyl group, a 2,2,3,3-tetrafluorocyclopropyl group and the like; bromine substituted cycloalkyl groups such as a 2-bromocyclohexyl group and the like; and iodine substituted cycloalkyl groups such as a 2-iodocyclohexyl group and the like.

Examples of the alkenyl group having 2 to 6 carbons substituted with halogen include chlorine substituted alkenyl group such as a 2-chloro-2-propenyl group, a 5-chloro-4-pentenyl group and the like; and fluorine substituted alkenyl groups such as a 4,4,4-trifluoro-2-butenyl group, a 6,6,6-trifluoro-5-hexenyl and the like.

Examples of the aryl group include a phenyl group, a naphthyl group and the like.

Examples of the heterocycle include a pyridyl group, a pyrimidyl group, a thienyl group, a furanyl group, a pyrazolyl group, an imidazolyl group, an isothiazolyl group, an isoxazolyl group, an indolyl group, a quinolyl group, a benzofuranyl group, a benzothienyl group, a benzoxazolyl group, a benzoisoxazolyl group, a benzimidazoly group, a benzothiazolyl group, a benzoisothiazolyl group and the like.

As the substituents of the aryl group and the heterocycle, there can be respectively exemplified, for example, alkyl groups such as a methyl group, an ethyl group, a propyl group, a butyl group and the like; cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like; halogen substituted alkyl groups such as a trifluoromethyl group, a difluoromethyl group, a bromodifluoromethyl group, a trifluoroethyl group and the like; alkoxy groups such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group and the like; halogen substituted alkoxy groups such as a trifluoromethoxy group, a difluoromethoxy group, a trifluoroethoxy group and the like; alkoxycarbonyl groups such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group and the like; aryloxycarbonyl groups such as a phenoxycarbonyl group and the like; alkylamino groups such as a methylamino group, an ethylamino group, a propylamino group, a butylamino group, a dimethylamino group and the like; cycloalkylamino groups such as a cyclopropylamino group, a cyclobutylamino group, a cyclopentylamino group, a cyclohexylamino group, a dicyclopropylamino group and the like; alkylcarbamoyl groups such as a methylcarbamoyl group, an ethylcarbamoyl group, a propylcarbamoyl group, a butylcarbamoyl group, a dimethylcarbamoyl group and the like; cycloalkylcarbamoyl groups such as a cyclopropylcarbamoyl group, a cyclobutylcarbamoyl group, a cyclopentylcarbamoyl group, a cyclohexylcarbamoyl group, a dicyclopropylcarbamoyl group and the like; alkylcarbonylamino groups such as a methylcarbonylamino group, an ethylcarbonylamino group, a propylcarbonylamino group, a butylcarbonylamino group and the like; cycloalkylcarbonylamino groups such as a cyclopropylcarbonylamino group, a cyclobutylcarbonylamino group, a cyclopentylcarbonylamino group, a cyclohexylcarbonylamino group and the like; alkyloxycarbonylamino groups such as a methyloxycarbonylamino group, an ethyloxycarbonylamino group, a propyloxycarbonylamino group, a butyloxycarbonylamino group and the like; cycloalkyloxycarbonylamino groups such as a cyclopropyloxycarbonylamino group, a cyclobutyloxycarbonylamino group, a cyclopentyloxycarbonylamino group, a cyclohexyloxycarbonylamino group and the like; alkylthio groups such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group and the like; halogen substituted alkylthio groups such as a trifluoromethylthio group, a difluoromethylthio group, a trifluoroethylthio group and the like; alkylsulfinyl groups such as a methanesulfinyl group, an ethanesulfinyl group, a propanesulfinyl group, a butanesulfinyl group and the like; halogen substituted alkylsulfinyl groups such as a trifluoromethanesulfinyl group, a difluoromethanesulfinyl group, a trifluoroethanesulfinyl group and the like; alkylsulfonyl groups such as a methanesulfonyl group, an ethanesulfonyl group, a propanesulfonyl group, a butanesulfonyl group and the like; halogen substituted alkylsulfonyl groups such as a trifluoromethanesulfonyl group, a difluoromethanesulfonyl group, a trifluoroethanesulfonyl group and the like; alkylsulfonamide groups such as a methanesulfonamide group, an ethanesulfonamide group, a propanesulfonamide group, a butanesulfonamide group and the like; halogen substituted alkylsulfonamide groups such as a trifluoromethanesulfonamide group, a difluoromethanesulfonamide group, a trifluoroethanesulfonamide group and the like; halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; and acyl groups such as an acetyl group, a benzoyl group and the like.

Typical preparation methods of the compound represented by the general formula (1) are illustrated below and the compound represented by the general formula (1) can be prepared according to the preparation methods, but the preparation method paths are not restricted to the following preparation methods. Preferable substituents or atoms in the compounds represented by the general formulae shown in the following preparation methods are illustrated below.

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

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

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

G₁a and G₂a are preferably independently an oxygen atom or a sulfur atom, and further preferably both of G₁a and G₂a are oxygen atoms.

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

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

X₃a and X₄a are preferably a hydrogen atom.

Y₁a and Y₅a are preferably independently 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 preferably a hydrogen atom, a halogen atom or a methyl group, and further preferably a hydrogen atom.

Q₁a is preferably a phenyl group,

a pyridyl group, or

and further preferably a phenyl group,

a pyridyl group, or

R_aand R_bare preferably independently a fluorine atom, a trifluoromethyl group, a pentafluoroethyl group or a heptafluoro-n-propyl group, and further preferably independently a fluorine atom, a trifluoromethyl group or a pentafluoroethyl group.

R_cis preferably a hydroxy 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 further preferably a hydroxy 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 further preferably a hydroxy group, a chlorine atom or a bromine atom.

R_c′ is preferably a hydroxy group.

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

In the general formulae shown in the following preparation methods, X₁, X₂, X₃, X₄, Y₁, Y₂, Y₄, Y₅, G₁, G₂, R₁, R₂and Q₁may independently correspond to X₁a, X₂a, X₃a, X₄a, Y₁a, Y₂a, Y₄a, Y₅a, G₁a, G₂a, R₁a, R₂a and Q₁a, or vice versa. Furthermore, Q₂represents the same as those in [1] or the general formula (A), (C) or (18),

wherein, in the formula, Y₁, Y₂, Y₃, Y₄and Y₅are the same as those described above,

wherein, in the formula, Y₁₁and Y₁₄may be the same or different and represent a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl 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 or a cyano group; Y₁₃represents a C1-C4 haloalkoxy group, a C2-C6 perfluoroalkyl group, a C2-C6 perfluoroalkylthio group, a C1-C6 perfluoroalkylsulfinyl group or a C1-C6 perfluoroalkylsulfonyl group; and Y₁₂represents a hydrogen atom, a halogen atom or a C1-C4 alkyl group, or

wherein, in the formula, Y₁a, Y₂a, Y₄a, Y₅a, R_a, R_band R_crepresent the same as those described above.

Preparation Method 1

wherein, in the formula, A₁, A₂, A₃, A₄, G₁, G₂, R₁, R₂, X, n, Q₁and Q₂represent the same as those described above; and L represents a functional group having a leaving ability such as a halogen atom, a hydroxy group or the like.

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

By reacting an m-nitroaromatic carboxylic acid derivative having a leaving group represented by the general formula (19) with an aromatic amine derivative represented by the general formula (20) in an appropriate solvent or without a solvent, an aromatic carboxylic acid amide derivative having a nitro group represented by the general formula (21) can be prepared. In the process, a suitable base can also be used.

Solvents may not remarkably hinder the progress of the reaction and examples thereof include water; aromatic hydrocarbons such as benzene, toluene, xylene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and the like; chained ethers or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as methanol, ethanol and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitrites such as acetonitrile and the like; and inert solvents such as 1,3-dimethyl-2-imidazolidinone and the like. These solvents can be used singly or in combination of 2 or more kinds.

The reaction temperature may be suitably selected in the range of −20 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.

Of the compounds represented by the general formula (19), an aromatic carboxylic acid halide derivative can be easily prepared from an aromatic carboxylic acid according to a usual method employing a halogenating agent. Examples of the halogenating agent include thionyl chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride, phosphorus trichloride and the like.

On the other hand, the compound represented by the general formula (21) can be prepared from the m-nitroaromatic carboxylic acid derivative and the compound represented by the general formula (20) without using a halogenating agent. As a method thereof, a method suitably using an additive such as 1-hydroxybenzotriazole or the like and employing a condensation agent using N,N′-dicyclohexylcarbodiimide according to a method as described, for example, in Chem. Ber. p. 788 (1970) can be exemplified. Other condensation agents to be used in this case include, for example, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, 1,1′-carbonylbis-1H-imidazole and the like.

Furthermore, as other method for preparing the compound represented by the general formula (21), a mixed anhydride procedure using chloroformate esters can be cited. Also, the compound represented by the general formula (21) can be prepared according to a method as described in J. Am. Chem. Soc. p. 5012 (1967). Examples of chloroformate esters to be used in this case include isobutyl chloroformate, isopropyl chloroformate and the like. In addition to chloroformate esters, diethylacetyl chloride, trimethylacetyl chloride and the like can be cited.

Both the method using a condensation agent and mixed anhydride procedure are not restricted to the solvent, reaction temperature and reaction time as described in the above literatures, and an inert solvent which does not remarkably hinder the suitable progress of the reaction may be used. The reaction temperature and reaction time may be suitably selected as the reaction proceeds.

1-(ii): General Formula (21)→General Formula (22)

An aromatic carboxylic acid amide derivative having a nitro group represented by the general formula (21) can be made into an aromatic carboxylic acid amide derivative having an amino group represented by the general formula (22) by the reduction reaction. As the reduction reaction, a method employing the hydrogenation reaction and a method employing a metallic compound (for example, stannous chloride (anhydride), iron powder, zinc powder and the like) can be cited.

The former method can be carried out in a proper solvent in the presence of a catalyst, at ordinary pressure or under pressure, in a hydrogen atmosphere. Examples of the catalyst include, for example, palladium catalysts such as palladium carbon and the like, nickel catalysts such as Raney nickel and the like, cobalt catalysts, ruthenium catalysts, rhodium catalysts, platinum catalysts and the like. Examples of the solvent include, for example, water; alcohols such as methanol, ethanol and the like; aromatic hydrocarbons such as benzene, toluene and the like; chained ethers or cyclic ethers such as ether, dioxane, tetrahydrofuran and the like; and esters such as ethyl acetate and the like. The pressure may be suitably selected in the range of 0.1 to 10 MPa, the reaction temperature may be suitably selected in the range of −20 degree centigrade to the reflux temperature of a solvent in use, and the reaction time may be properly selected in the range of several minutes to 96 hours. The compound of the general formula (22) can be more effectively prepared.

As the latter method, a method employing stannous chloride (anhydride) as a metallic compound according to the conditions as described in “Organic Syntheses” Coll. Vol. III P. 453 can be cited.

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

By reacting an aromatic carboxylic acid amide derivative having an amino group represented by the general formula (22) with a compound represented by the general formula (23) in an appropriate solvent, a compound represented by the general formula (24) of the present invention can be prepared. In this process, a suitable base can also be used.

Furthermore, examples of the base include organic bases such as triethylamine, tri-n-butylamine, pyridine, 4-dimethylaminopyridine and the like; alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and the like; carbonates such as sodium hydrogen carbonate, potassium carbonate and the like; phosphates such as di-potassium mono-hydrogen phosphate, tri-sodium phosphate and the like; alkali metal hydrides such as sodium hydride and the like; and alkali metal alcoholates such as sodium methoxide, sodium ethoxide and the like. These bases may be suitably selected in the range of 0.01 to 5 mole equivalents based on the compound represented by the general formula (22) and used accordingly. The reaction temperature may be suitably selected in the range of −20 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours. Furthermore, a method employing a condensation agent and a mixed anhydride procedure as described in 1-(i) can also be used for the production thereof.

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

By reacting a compound represented by the general formula (24) with an alkyl compound having a leaving group represented by the general formula (25) in a solvent or without a solvent, a compound represented by the general formula (26) of the present invention can be prepared. Examples of the compound represented by the general formula (25) include alkyl halides such as methyl iodide, ethyl iodide, n-propyl bromide and the like. Furthermore, in this process, a suitable base or solvent can be used. As the base or solvent, the bases or solvents cited in 1-(i) can be used. The reaction temperature and reaction time cited in 1-(i) can also be used.

Furthermore, the compound represented by the general formula (26) can also be prepared by a separate method comprising reacting an alkylating agent such as dimethyl sulfate, diethyl sulfate or the like, instead of the compound represented by the general formula (25), with the compound represented by the general formula (24).

Preparation Method 2

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

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

By reacting a carboxylic acid having an amino group represented by the general formula (27) as a starting material with a compound represented by the general formula (23) in accordance with the conditions described in 1-(i), carboxylic acids having an acylamino group represented by the general formula (28) can be prepared.

2-(ii): General Formula (28)→General Formula (29)

A compound represented by the general formula (29) can be prepared by a known usual method comprising reacting a compound represented by the general formula (28) with thionyl chloride, oxalyl chloride, phosgene, phosphorus oxychloride, phosphorus pentachloride, phosphorus trichloride, thionyl bromide, phosphorus tribromide, diethylaminosulfur trifluoride or the like.

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

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

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

By reacting a compound represented by the general formula (28) with a compound represented by the general formula (20) according to the conditions using a condensation agent or a mixed anhydride procedure described in 1-(i), a compound represented by the general formula (30) can be prepared.

Preparation Method 3

wherein, in the formula, A₁, A₂, A₃, A₄, G₁, R₁, R₂, X, n, Q₁, Q₂and L are the same as those described above.

3-(i): General Formula (31)→General Formula (32)

By reacting a compound represented by the general formula (31) with a Lawson reagent according to the known conditions described in Synthesis p. 463 (1993), Synthesis p. 829 (1984) and the like, a compound represented by the general formula (32) can be prepared. The conditions such as a solvent, reaction temperature and the like are not restricted to those described in the literatures.

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

By reacting a compound represented by the general formula (32) with a compound represented by the general formula (23) according to the conditions described in 1-(i), a compound represented by the general formula (33) can be prepared.

Preparation Method 4

wherein, in the formula, A₁, A₂, A₃, A₄, R₁, R₂, X, n, Q₁and Q₂are the same as those described above.

Compounds represented by the general formulae (35) and (36) can be prepared from a compound represented by the general formula (34) according to the conditions described in 3-(i). The conditions such as a solvent, reaction temperature and the like are not restricted to those described in the literatures. These two compounds can be easily separated and purified by a known separation and purification technique such as silica gel column chromatography and the like.

Preparation Method 5

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

5-(i): General Formula (37)→General Formula (38)

A compound represented by the general formula (38) can be prepared by carrying out an amination reaction using ammonia according to the conditions described, for example, in J. Org. Chem. p. 280 (1958). However, the conditions such as a reaction solvent and the like are not restricted to those described in the literatures, and an inert solvent which does not remarkably hinder the proper progress of the reaction may be used. The reaction temperature and reaction time may be suitably selected as the reaction proceeds. Furthermore, examples of the amination agent include methylamine, ethylamine or the like, in addition to ammonia.

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

By reacting a compound represented by the general formula (38) with a compound represented by the general formula (23) according to the conditions described in 1-(i), a compound represented by the general formula (39) can be prepared.

Preparation Method 6

wherein, in the formula, R₂represents the same as those described above; Y₁and Y₅independently represent a methyl group, a chlorine atom, a bromine atom or an iodine atom; Y₂and Y₄represent the same as those described above; R_frepresents a C1-C6 perfluoroalkyl group; and m represents 1 or 2.

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

By reacting aminothiophenols represented by the general formula (40) with haloalkyl iodide represented by the general formula (41) in accordance with a method described in J. Fluorine Chem. p. 207 (1994), a compound represented by the general formula (42) can be prepared.

Examples of haloalkyl iodide represented by the general formula (41) include trifluoromethyl iodide, pentafluoroethyl iodide, heptafluoro-n-propyl iodide, heptafluoroisopropyl iodide, nonafluoro-n-butyl iodide, nonafluoroisobutyl iodide and the like. These may be suitably used in the range of 1 to 10 mole equivalents, based on the compound represented by the general formula (40).

The solvent to be used in the process is not restricted to solvents described in the above literatures and may not remarkably hinder the progress of the reaction. Examples thereof include water; aromatic hydrocarbons such as benzene, toluene, xylene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and the like; chained ethers or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as methanol, ethanol and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitrites such as acetonitrile and the like; and inert solvents such as 1,3-dimethyl-2-imidazolidinone, hexamethylphosphoric triamide and the like. These solvents can be used singly or in combination of 2 or more kinds. Particularly preferable is a polar solvent. The reaction temperature may be suitably selected in the range of −20 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.

6-(ii): General Formula (42)→General Formula (43)

A compound represented by the general formula (43) can be prepared by using a suitable halogenating agent. For example, a method as described in Synth. Commun. p. 1261 (1989) can be cited.

Examples of the halogenating agent include chlorine, bromine, iodine, N-chlorosuccinic acid imide, N-bromosuccinic acid imide, N-iodosuccinic acid imide and the like. These may be suitably used in the range of 1 to 10 mole equivalents, based on a compound represented by the general formula (42).

In the process, an appropriate solvent can also be used, but a solvent in use is not restricted to solvents described in the above literatures and may not remarkably hinder the progress of the reaction. Examples thereof include water; aromatic hydrocarbons such as benzene, toluene, xylene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and the like; chained ethers or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as methanol, ethanol and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitrites such as acetonitrile and the like; and inert solvents such as 1,3-dimethyl-2-imidazolidinone, hexamethylphosphoric triamide and the like. These solvents can be used singly or in combination of 2 or more kinds. Particularly preferable is a polar solvent. The reaction temperature may be suitably selected in the range of −20 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.

6-(iii): General Formula (43)→General Formula (44)

A compound represented by the general formula (44) can be prepared by using a suitable oxidant. A method described, for example, in Tetrahedron Lett. p. 4955 (1994) can be cited. Examples of the oxidant include organic peroxides such as m-chloroperbenzoic acid and the like, sodium metaperiodate, hydrogen peroxide, ozone, selenium dioxide, chromic acid, dinitrogen tetraoxide, acyl nitrate, iodine, bromine, N-bromosuccinic acid imide, iodosylbenzyl, t-butyl hypochlorite and the like. The solvent to be used in this process is not restricted to solvents described in the above literatures and may not remarkably hinder the progress of the reaction. These solvents can be used singly or in combination of 2 or more kinds. Particularly preferable is a polar solvent. The reaction temperature may be suitably selected in the range of −20 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.

6-(iv): General Formula (43)→General Formula (43-2)

A compound represented by the general formula (43-2) (wherein, in the formula, any one of Y₁and Y₅must represent a methyl group) can be prepared from a compound represented by the general formula (43) by using a suitable methylating agent. In this process, a method described, for example, in Tetrahedron Lett. p. 6237 (2000) can be cited.

6-(v): General Formula (43-2)→General Formula (44-2)

A compound represented by the general formula (44-2) (wherein, in the formula, any one of Y₁and Y₅must represent a methyl group) can be prepared according to the method described in 6-(iii).

Furthermore, the compound of the present invention can be prepared by suitably selecting a preparation method as illustrated in the present invention using an aniline derivative represented by the general formula (43), (44), (43-2) or (44-2).

Preparation Method 7

wherein, in the formula, R₂, Y₁, Y₂, Y₄, Y₅, R_fand m represent the same as those described in the preparation method 6.

An aniline derivative represented by the general formula (47) can be prepared using a compound represented by the general formula (45) as a starting raw material according to the preparation method 6. Furthermore, by suitably selecting a preparation method as illustrated in the present invention, the compound of the present invention can be prepared.

Preparation Method 8

wherein, in the formula, A₁, A₂, A₃, A₄, X, n, G₂, R₂and Q₂represent the same as those above.

By reacting a compound represented by the general formula (48) with a suitable reactant using an appropriate base in a proper solvent, a compound represented by the general formula (49) can be prepared.

Solvents may not remarkably hinder the progress of the reaction and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile, propionitrile and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone, methylethyl ketone and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as methanol, ethanol and the like; 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethylsulfoxide; water and the like. These solvents can be used singly or in combination of 2 or more kinds.

Examples of the base include organic bases such as triethylamine, tributylamine, pyridine, 4-dimethylaminopyridine and the like; alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and the like; carbonates such as sodium hydrogen carbonate, potassium carbonate and the like; phosphates such as potassium mono-hydrogen phosphate, tri-sodium phosphate and the like; alkali metal hydrides such as sodium hydride and the like; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and the like; organolithiums such as n-butyl lithium and the like; and Grignard reagents such as ethyl magnesium bromide and the like.

These bases may be suitably selected in the range of 0.01 to 5 mole equivalents, based on the compound represented by the general formula (48) or may be used as a solvent.

Examples of the reactant include halogenated alkyls such as methyl iodide, ethyl bromide, trifluoromethyl iodide, 2,2,2-trifluoroethyl iodide and the like; halogenated allyls such as allyl iodide and the like; halogenated propargyls such as propargyl bromide and the like; halogenated acyls such as acetyl chloride and the like; acid anhydrides such as trifluoroacetic anhydride and the like; and alkyl sulfuric acids such as dimethyl sulfate, diethyl sulfate and the like.

These reactants may be suitably selected in the range of 1 to 5 mole equivalents, based on the compound represented by the general formula (48) or may be used as a solvent.

The reaction temperature may be suitably selected in the range of −80 degree centigrade to the reflux temperature of a solvent in use, while the reaction time may be properly selected in the range of several minutes to 96 hours.

Preparation Method 9

wherein, in the formula, A₁, A₂, A₃, A₄, X, n, G₂, R₁, R₂and Q₂represent the same as those described above.

9-(i): General Formula (22)→General Formula (50)

By reacting a compound represented by the general formula (22) with aldehydes or ketones in an appropriate solvent, adding a suitable catalyst and reacting the resultant in a hydrogen atmosphere, a compound represented by the general formula (50) can be prepared.

Solvents may not remarkably hinder the progress of the reaction and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile, propionitrile and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone, methylethyl ketone and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethylsulfoxide, methanol, ethanol and the like; water and the like. These solvents can be used singly or in combination of 2 or more kinds.

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

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

Examples of ketones include acetone, perfluoroacetone, methylethyl ketone and the like.

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

9-(ii): General Formula (22)→General Formula (50) (Separate Method 1)

By reacting a compound represented by the general formula (22) with aldehydes or ketones in an appropriate solvent, and applying a suitable reducing agent, a compound represented by the general formula (50) can be prepared.

Solvents may not remarkably hinder the progress of the reaction and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitriles such as acetonitrile, propionitrile and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone, methylethyl ketone and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethylsulfoxide, methanol, ethanol and the like; water and the like. These solvents can be used singly or in combination of 2 or more kinds.

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

Examples of ketones include acetone, perfluoroacetone, methylethyl ketone and the like.

9-(iii): General Formula (22)→General Formula (50) (Separate Method 2)

By reacting a compound represented by the general formula (22) with a formylating agent in an appropriate solvent or without a solvent and applying a proper additive, it is possible to prepare a compound, wherein, in the general formula (50), R₁is a methyl group.

Solvents may not remarkably hinder the progress of the reaction and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitrites such as acetonitrile, propionitrile and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone, methylethyl ketone and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethylsulfoxide, methanol, ethanol and the like; water and the like. These solvents can be used singly or in combination of 2 or more kinds.

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

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

Preparation Method 10

wherein, in the formula, X₁a, X₂a, X₃a, X₄a, Y₁a, Y₂a, Y₄a, Y₅a, G₂a, R₂a, R_aand R_brepresent the same as those described above; in the general formula (51), R_c′ represents a hydroxy group or —O—R_dR_drepresents the same as those described above); and in the general formula (52), R_e″ represents a chlorine atom, a bromine atom or an iodine atom.

By reacting a compound represented by the general formula (51) with a suitable halogenating agent in an appropriate solvent or without a solvent, a chlorine compound (a bromine compound or an iodine compound) represented by the general formula (52) can be prepared. In the process, an appropriate additive can also be used.

Solvents may not remarkably hinder the progress of the reaction and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitrites such as acetonitrile, propionitrile and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethylsulfoxide, methanol, ethanol and the like; water and the like. These solvents can be used singly or in combination of 2 or more kinds.

Examples of the halogenating agent include thionyl chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride, phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, Rydon reagents, sulfonyl halides such as methanesulfonyl chloride, p-toluenesulfonyl chloride, benzenesulfonyl chloride and the like, sulfonium halides, sulfonate esters, chlorine, bromine, iodine, hypohalite esters, N-halogenoamines, 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-dimethyl phosphoamidine dichloride and the like.

Examples of the additive include metal salts such as zinc chloride, lithium bromide and the like; organic bases such as a phase transfer catalyst, hexamethylphosphoric triamide and the like; inorganic acids such as sulfuric acid and the like; N,N-dimethylformamide and the like.

These halogenating agents may be suitably selected in the range of 0.01 to 10 mole equivalents, based on the compound represented by the general formula (1) or may be used as a solvent.

Preparation Method 11

wherein, in the formula, X₁a, X₂a, X₃a, X₄a, Y₁a, Y₂a, Y₄a, Y₅a, G₂a, R₁a, R₂a, R_a, R_band R_crepresent the same as those described above.

By reacting a compound represented by the general formula (53) with a suitable fluorinating agent in an appropriate solvent or without a solvent, a compound represented by the general formula (54) can be prepared.

Solvents may not remarkably hinder the progress of the reaction and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane and the like; aromatic hydrocarbons such as benzene, xylene, toluene and the like; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane and the like; ethers such as diethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane and the like; amides such as dimethylformamide, dimethylacetamide and the like; nitrites such as acetonitrile, propionitrile and the like; ketones such as acetone, methylisobutyl ketone, cyclohexanone, methylethyl ketone and the like; esters such as ethyl acetate, butyl acetate and the like; alcohols such as 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethylsulfoxide, methanol, ethanol and the like; water and the like. These solvents can be used singly or in combination of 2 or more kinds.

Examples of the fluorinating agent include 1,1,2,2-tetrafluoroethyldiethylamine, 2-chloro-1,1,2-trifluoroethyldiethylamine, trifluorodiphenylphosphorane, difluorotriphenylphosphorane, fluoroformate 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 (IV) fluoride, tris(dimethylamino)sulfonium difluorotrimethylsilicate, sodium hexafluorosilicate, quaternary ammonium fluoride, (2-chloroethyl)diethylamine, diethylaminosulfur trifluoride, morpholinosulfur trifluoride, silicon tetrafluoride, hydrogen fluoride, hydrofluoric acid, hydrogen fluoride pyridine complex, hydrogen fluoride triethylamine complex, hydrogen fluoride salt, bis(2-methoxyethyl)aminosulfur trifluoride, 2,2-difluoro-1,3-dimethyl-2-imidazolidinone, iodine pentafluoride, tris(diethylamino)phosphonium-2,2,3,3,4,4-hexafluoro-cyclobutane ylide, triethylammonium hexafluorocyclobutane ylide, hexafluoropropene and the like. These fluorinating agents can be used singly or in combination of 2 or more kinds. These halogenating agents may be suitably selected in the range of 1 to 10 mole equivalents, based on the compound represented by the general formula (53) or may be suitably used as a solvent.

An additive may also be used and examples thereof include crown ethers such as 18-crown-6 and the like; phase transfer catalysts such as tetraphenylphosphonium salts and the like; inorganic salts such as calcium fluoride, calcium chloride and the like; metal oxides such as mercury oxide and the like; ion exchange resins and the like. These additives can be not only added in the reaction system, but also used as a pretreatment agent of the fluorinating agent.

Preparation Method 12

wherein, in the formula, X₁a, X₂a, X₃a, X₄a, Y₁a, Y₂a, Y₄a, Y₅a, G₂a, R₁a, R₂a, R_a, R_b, R_c′ and R_c″ represent the same as those described above.

A compound represented by the general formula (56) can be prepared from a compound represented by the general formula (55) according to the method described in the preparation method 10.

Preparation Method 13

wherein, in the formula, X₁a, X₂a, X₃a, X₄a, Y₁a, Y₂a, Y₄a, Y₅a, G₁a, G₂a, R₁a, R₂a, R_a, R_b, R_cand Q₁a represent the same as those described above.

A compound represented by the general formula (58) can be prepared from a compound represented by the general formula (57) according to the method described in the preparation method 11.

Preparation Method 14

wherein, in the formula, X₁a, X₂a, X₃a, X₄a, Y₁a, Y₂a, Y₄a, Y₅a, G₁a, G₂a, R₁a, R₂a, R_a, R_b, R_c′, R_c″ and Q₁a represent the same as those described above.

A compound represented by the general formula (60) can be prepared from a compound represented by the general formula (59) according to the method described in the preparation method 10.

In all preparation methods as illustrated above, desired products may be isolated according to a usual method from the reaction system after completion of the reaction, and can be purified, if needed, by carrying out operations such as recrystallization, column chromatography, distillation and the like. Furthermore, desired products can also be supplied to the next reaction process without isolating them from the reaction system.

The compound represented by the general formula (2) can be prepared according to a method as described in International Publication No. 2005/21488 pamphlet.

The compound represented by the general formula (3) can be prepared according to a method as described in International Publication No. 2003/8372 pamphlet.

The compound represented by the general formula (4) can be prepared according to a method as described in International Publication No. 2005/42474 pamphlet.

Typical compounds of the compound represented by the general formula (1) that is an active ingredient of an insecticide of the present invention are illustrated in Tables 1 to 5 below, but the present invention is not restricted thereto.

Incidentally, in the tables, “n-” refers to normal, “Me” refers to a methyl group, “Et” refers to an ethyl group, “n-Pr” refers to a normal propyl group, “i-Pr” refers to an isopropyl group, “n-Bu” refers to a normal butyl group, “i-Bu” refers to an isobutyl group, “s-Bu” refers to a secondary butyl group, “t-Bu” refers to a tertiary butyl group, “H” refers to a hydrogen atom, “O” refers to an oxygen atom, “S” refers to a sulfur atom, “C” refers to a carbon atom, “N” refers to a nitrogen atom, “F” refers to a fluorine atom, “Cl” refers to a chlorine atom, “Br” refers to a bromine atom, “I” refers to an iodine atom, “CF₃” refers to a trifluoromethyl group, “MeS” refers to a methylthio group, “MeSO” refers to a methylsulfinyl group, “MeSO₂” refers to a methylsulfonyl group, “MeO” refers to a methoxy group, “NH₂” refers to an amino group, “MeNH” refers to a methylamino group, “Me₂N” refers to a dimethylamino group, and “OH” refers to a hydroxy group.

(X₁, X₂, X₃, X₄=hydrogen atoms; G₁, G₂=oxygen atoms; R₁, R₂=hydrogen atoms)

TABLE 1

Compound

Nos.
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-(heptafluoroisopropyl)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)phenyl
2,6-dimethyl-4-(heptafluoroisopropyl)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-bipheny
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
pyridine-2-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

124
4-trifluoromethylpyrimidine-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-4H pyran-3-yl
2,6-dimethyl-4-(heptafluoroisopropyl)phenyl

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

162
2-phenylquinoline-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-(heptafluoroisapropyl)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-chloropyridine-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-chloropyridine-3-yl
2-bromo-4-(heptafluoroisopropyl)-6-(methylsulfonyl)phenyl

209
phenyl
4-(heptafluoroisopropyl)-2-methyl-thiomethyl-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
pyridine-2-yl
2,6-dimethyl-4-(nonafluoro-2-butyl)phenyl

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

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

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

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

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

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

255
2,6-difluorophenyl
2,6-dicloro-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-(pentafluoromethylthio)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-5-(methylsulfonylamino)phenyl
2,6-dibromo-4-(heptafluoro-n-propylthio)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
pyridine-2-yl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl

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

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

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

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

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

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

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

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

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

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

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

318
1-methyl-3-tri-fluoromethyl-1H-pyrazole-4-yl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl

319
1-methyl-5-tri-fluoromethyl-1H-pyrazole-4-yl
2,6-dibromo-4-(heptafluoro-n-propylthio)phenyl

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

321
2-phenylthiazole-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
thiophene-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-(heptafluor-n-propylthio)phenyl

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

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

331
2-chloropyridine-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-(heptafluoro-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
pyridine-2-yl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl

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

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

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

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

371
2-methylthiopyridine-3-yl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)phenyl

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

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

374
thiophene-2-yl
2,6-dibromo-4-(heptafluoro-n-propylsulfinyl)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-chloro2-nitrophenyl
2,6-dibromo-4-(heptafluoro-n-propylsulfonyl)phenyl

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

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

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

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

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

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

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

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

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

419
thiophene-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
pyridine-2-yl
2,6-dimethyl-4-(heptafluoro-n-propylthio)phenyl

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

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

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

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

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

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

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

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

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

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

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

463
phenyl
2,4-dimethyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy)pridine-3-yl

464
phenyl
2-chloro-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyridine-3-yl

465
phenyl
2-bromo-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyridine-3-yl

466
2-fluorophenyl
2-bromo-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyridine-3-yl

467
phenyl
2-iodo-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyridine3-yl

(G₁, G₂=oxygen atoms; R₁, R₂=hydrogen atoms)

TABLE 2

Com-

pound

Nos.
Q₁
X₁
X₂
X₃
X₄
Q₂

601
phenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

602
2-methylphenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

603
3-methylphenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

604
4-methylphenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

605
2-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

606
3-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

607
4-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

608
3-cyanophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

609
4-cyanophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

610
2-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

611
3-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

612
4-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

613
2-chlorophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

614
4-chlorophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

615
2-bromophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

616
2-iodophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

617
2-trifluoromethyl
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

618
4-trifluoromethyl
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

619
4-trifluorometh-
F
H
H
H
2,6-dimethyl-4-(hepta-

oxyphenyl

fluoroisopropyl)phenyl

620
4-(dimethyl-
F
H
H
H
2,6-dimethyl-4-(hepta-

amino)phenyl

fluoroisopropyl)phenyl

621
2,3-difluoro-
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

622
2,4-difluoro-
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

623
2,5-difluoro-
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

624
2,6-difluoro-
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

625
2,4-dichloro-
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

626
2,6-dichloro-
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

627
3,4-dichloro-
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

628
2-fluoro-4-nitro
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

629
4-fluoro-2-nitro
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

630
2-chloro-4-fluoro
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

631
4-chloro-2-fluoro
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

632
2-chloro-6-fluoro
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

633
2-chloro-4-nitro
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

634
4-chloro-2-nitro
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

635
2,3,6-trifluoro
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

636
pyridine-2-yl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

637
pyridine-3-yl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

638
2-fluoropyridine-
F
H
H
H
2,6-dimethyl-4-(hepta-

3-yl

fluoroisopropyl)phenyl

639
2-chloropyridine-
F
H
H
H
2,6-dimethyl-4-(hepta-

3-yl

fluoroisopropyl)phenyl

640
2-chloropyridine-
F
H
H
H
2,6-dimethyl-4-(hepta-

5-yl

fluoroisopropyl)phenyl

641
2-methylthio
F
H
H
H
2,6-dimethyl-4-(hepta-

pyridine-3-yl

fluoroisopropyl)phenyl

642
pyrazine-2-yl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

643
furan-2-yl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

644
furan-3-yl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

645
2-tetrahydrofuranyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

646
benzofuran-2-yl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

647
thiophene-2-yl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

648
2-methyl-5,6-
F
H
H
H
2,6-dimethyl-4-(hepta-

dihydro-4H-pyran-

fluoroisopropyl)phenyl

3-yl

649
phenyl
H
Cl
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

650
phenyl
H
F
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

651
4-nitrophenyl
H
F
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

652
4-cyanophenyl
H
F
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

653
2-fluorophenyl
H
F
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

654
4-fluorophenyl
H
F
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

655
4-trifluoromethyl
H
F
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

656
2,4-difluorophenyl
H
F
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

657
2-chloropyridine-
H
F
H
H
2,6-dimethyl-4-(hepta-

3-yl

fluoroisopropyl)phenyl

658
phenyl
H
H
CF₃
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

659
phenyl
H
H
H
F
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

660
phenyl
H
H
H
Cl
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

661
phenyl
H
H
H
Br
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

662
phenyl
H
H
H
I
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

663
phenyl
F
H
H
F
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

664
phenyl
H
Br
H
Br
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

665
phenyl
F
H
H
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

666
2-methylphenyl
F
H
H
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

667
4-methylphenyl
F
H
H
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

668
2-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

669
3-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

670
4-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

671
2-chlorophenyl
F
H
H
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

672
4-chlorophenyl
F
H
H
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

673
2-bromophenyl
F
H
H
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

674
2-iodophenyl
F
H
H
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

675
3-cyanophenyl
F
H
H
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

676
4-cyanophenyl
F
H
H
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

677
2-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

678
3-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

679
4-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

680
2-trifluoromethyl
F
H
H
H
2,6-dimethyl-4-(nona-

phenyl

fluoro-2-butyl)phenyl

681
4-trifluoromethyl
F
H
H
H
2,6-dimethyl-4-(nona-

phenyl

fluoro-2-butyl)phenyl

682
4-trifluorometh-
F
H
H
H
2,6-dimethyl-4-(nona-

oxyphenyl

fluoro-2-butyl)phenyl

683
2,3-difluoro-
F
H
H
H
2,6-dimethyl-4-(nona-

phenyl

fluoro-2-butyl)phenyl

684
2,4-difluoro-
F
H
H
H
2,6-dimethyl-4-(nona-

phenyl

fluoro-2-butyl)phenyl

685
2,5-difluoro-
F
H
H
H
2,6-dimethyl-4-(nona-

phenyl

fluoro-2-butyl)phenyl

686
2,6-difluoro-
F
H
H
H
2,6-dimethyl-4-(nona-

phenyl

fluoro-2-butyl)phenyl

687
2,4-dichloro-
F
H
H
H
2,6-dimethyl-4-(nona-

phenyl

fluoro-2-butyl)phenyl

688
2,6-dichloro-
F
H
H
H
2,6-dimethyl-4-(nona-

phenyl

fluoro-2-butyl)phenyl

689
3,4-dichloro-
F
H
H
H
2,6-dimethyl-4-(nona-

phenyl

fluoro-2-butyl)phenyl

690
2-chloro-4-nitro
F
H
H
H
2,6-dimethyl-4-(nona-

phenyl

fluoro-2-butyl)phenyl

691
2-chloro-4-fluoro
F
H
H
H
2,6-dimethyl-4-(nona-

phenyl

fluoro-2-butyl)phenyl

692
2-chloro-6-fluoro
F
H
H
H
2,6-dimethyl-4-(nona-

phenyl

fluoro-2-butyl)phenyl

693
4-chloro-2-fluoro
F
H
H
H
2,6-dimethyl-4-(nona-

phenyl

fluoro-2-butyl)phenyl

694
4-chloro-2-nitro
F
H
H
H
2,6-dimethyl-4-(nona-

phenyl

fluoro-2-butyl)phenyl

695
2,3,6-trifluoro
F
H
H
H
2,6-dimethyl-4-(nona-

phenyl

fluoro-2-butyl)phenyl

696
pyridine-2-yl
F
H
H
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

697
pyridine-3-yl
F
H
H
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

698
2-fluoropyridine-
F
H
H
H
2,6-dimethyl-4-(nona-

3-yl

fluoro-2-butyl)phenyl

699
2-chloropyridine-
F
H
H
H
2,6-dimethyl-4-(nona-

3-yl

fluoro-2-butyl)phenyl

700
2-chloropyridine-
F
H
H
H
2,6-dimethyl-4-(nona-

5-yl

fluoro-2-butyl)phenyl

701
2-methylthio
F
H
H
H
2,6-dimethyl-4-(nona-

pyridine-3-yl

fluoro-2-butyl)phenyl

702
pyrazine-2-yl
F
H
H
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

703
furan-2-yl
F
H
H
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

704
furan-3-yl
F
H
H
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

705
2-tetrahydro-
F
H
H
H
2,6-dimethyl-4-(nona-

furanyl

fluoro-2-butyl)phenyl

706
benzofuran-2-yl
F
H
H
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

707
thiophene-2-yl
F
H
H
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

708
phenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

709
2-methylphenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

710
4-methylphenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

711
2-fluorophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

712
3-fluorophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

713
4-fluorophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

714
2-chlorophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

715
4-chlorophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

716
2-bromophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

717
2-iodophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

718
3-cyanophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

719
4-cyanophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

720
2-nitrophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

721
3-nitrophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

722
4-nitrophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

723
2-trifluoromethyl
F
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

724
4-trifluoromethyl
F
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

725
4-trifluorometh-
F
H
H
H
2,6-dibromo-4-(hepta-

oxyphenyl

fluoro-n-propylthio)

phenyl

726
2,3-difluoro-
F
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

727
2,4-difluoro-
F
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

728
2,5-difluoro-
F
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

729
2,6-difluoro-
F
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

730
2,4-dichloro-
F
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

731
2,6-dichloro-
F
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

732
3,4-dichloro-
F
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

733
2-chloro-4-nitro
F
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

734
2-chloro-4-fluoro
F
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

735
2-chloro-6-fluoro
F
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

736
4-chloro-2-fluoro
F
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

737
4-chloro-2-nitro
F
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

738
2,3,6-trifluoro
F
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

739
pyridine-2-yl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

740
pyridine-3-yl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

741
2-fluoropyridine-
F
H
H
H
2,6-dibromo-4-(hepta-

3-yl

fluoro-n-propylthio)

phenyl

742
2-chloropyridine-
F
H
H
H
2,6-dibromo-4-(hepta-

3-yl

fluoro-n-propylthio)

phenyl

743
2-chloropyridine-
F
H
H
H
2,6-dibromo-4-(hepta-

5-yl

fluoro-n-propylthio)

phenyl

744
2-methylthio
F
H
H
H
2,6-dibromo-4-(hepta-

pyridine-3-yl

fluoro-n-propylthio)

phenyl

745
pyrazine-2-yl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

746
furan-2-yl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

747
furan-3-yl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

748
2-tetrahydro-
F
H
H
H
2,6-dibromo-4-(hepta-

furanyl

fluoro-n-propylthio)

phenyl

749
benzofuran-2-yl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

750
thiophene-2-yl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

751
phenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

752
2-methylphenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

753
4-methylphenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

754
2-fluorophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

755
3-fluorophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

756
4-fluorophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

757
2-chlorophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

758
4-chlorophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

759
2-bromophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

760
2-iodophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

761
3-cyanophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

762
4-cyanophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

763
2-nitrophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

764
3-nitrophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

765
4-nitrophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

766
2-trifluoromethyl
F
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

767
4-trifluoromethyl
F
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

768
4-trifluorometh-
F
H
H
H
2,6-dibromo-4-(hepta-

oxyphenyl

fluoro-n-propylsul-

finyl)phenyl

769
2,3-difluorophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

770
2,4-difluorophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

771
2,5-difluorophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

772
2,6-difluorophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

773
2,4-dichlorophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

774
2,6-dichlorophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

775
3,4-dichlorophenyl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

776
2-chloro-4-nitro
F
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

777
2-chloro-4-fluoro
F
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

778
2-chloro-6-fluoro
F
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

779
4-chloro-2-fluoro
F
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

780
4-chloro-2-nitro
F
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

781
2,3,6-trifluoro
F
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

782
pyridine-2-yl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

783
pyridine-3-yl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

784
2-fluoropyridine-
F
H
H
H
2,6-dibromo-4-(hepta-

3-yl

fluoro-n-propylsul-

finyl)phenyl

785
2-chloropyridine-
F
H
H
H
2,6-dibromo-4-(hepta-

3-yl

fluoro-n-propylsul-

finyl)phenyl

786
2-chloropyridine-
F
H
H
H
2,6-dibromo-4-(hepta-

5-yl

fluoro-n-propylsul-

finyl)phenyl

787
2-methylthio
F
H
H
H
2,6-dibromo-4-(hepta-

pyridine-3-yl

fluoro-n-propylsul-

finyl)phenyl

788
pyrazine-2-yl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

789
furan-2-yl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

790
thiophene-2-yl
F
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

791
phenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoro-n-propylthio)

phenyl

792
2-methylphenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoro-n-propylthio)

phenyl

793
4-methylphenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoro-n-propylthio)

phenyl

794
2-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoro-n-propylthio)

phenyl

795
3-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoro-n-propylthio)

phenyl

796
4-fluorophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoro-n-propylthio)

phenyl

797
2-chlorophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoro-n-propylthio)

phenyl

798
4-chlorophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoro-n-propylthio)

phenyl

799
2-bromophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoro-n-propylthio)

phenyl

800
2-iodophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoro-n-propylthio)

phenyl

801
3-cyanophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoro-n-propylthio)

phenyl

802
4-cyanophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoro-n-propylthio)

phenyl

803
2-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoro-n-propylthio)

phenyl

804
3-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoro-n-propylthio)

phenyl

805
4-nitrophenyl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoro-n-propylthio)

phenyl

806
2-trifluoromethyl
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

807
4-trifluoromethyl
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

808
4-trifluorometh-
F
H
H
H
2,6-dimethyl-4-(hepta-

oxyphenyl

fluoro-n-propylthio)

phenyl

809
2,3-difluoro-
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

810
2,4-difluoro-
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

811
2,5-difluoro-
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

812
2,6-difluoro-
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

813
2,4-dichloro-
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

814
2,6-dichloro-
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

815
3,4-dichloro-
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

816
2-chloro-4-nitro
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

817
2-chloro-4-fluoro
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

818
2-chloro-6-fluoro
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

819
4-chloro-2-fluoro
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

820
4-chloro-2-nitro
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

821
2,3,6-trifluoro
F
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

822
pyridine-2-yl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoro-n-propylthio)

phenyl

823
pyridine-3-yl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoro-n-propylthio)

phenyl

824
2-fluoropyridine-
F
H
H
H
2,6-dimethyl-4-(hepta-

3-yl

fluoro-n-propylthio)

phenyl

825
2-chloropyridine-
F
H
H
H
2,6-dimethyl-4-(hepta-

3-yl

fluoro-n-propylthio)

phenyl

826
2-chloropyridine-
F
H
H
H
2,6-dimethyl-4-(hepta-

5-yl

fluoro-n-propylthio)

phenyl

827
2-methylthio
F
H
H
H
2,6-dimethyl-4-(hepta-

pyridine-3-yl

fluoro-n-propylthio)

phenyl

828
pyrazine-2-yl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoro-n-propylthio)

phenyl

829
furan-2-yl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoro-n-propylthio)

phenyl

830
thiophene-2-yl
F
H
H
H
2,6-dimethyl-4-(hepta-

fluoro-n-propylthio)

phenyl

831
phenyl
Cl
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

832
2-fluorophenyl
Cl
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

833
2-chloropyridine-
Cl
H
H
H
2,6-dibromo-4-(hepta-

3-yl

fluoro-n-propylthio)

phenyl

(X₃, X₄=hydrogen atoms; G₁, G₂=oxygen atoms)

TABLE 3

Com-

pound

Nos.
Q₁
R₁
R₂
X₁
X₂
Q₂

1001
phenyl
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1002
2-methylphenyl
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1003
4-methylphenyl
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1004
2-fluorophenyl
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1005
3-fluorophenyl
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1006
4-fluorophenyl
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1007
2-chlorophenyl
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1008
4-chlorophenyl
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1009
2-bromophenyl
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1010
2-iodophenyl
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1011
3-cyanophenyl
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1012
4-cyanophenyl
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1013
2-nitrophenyl
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1014
3-nitrophenyl
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1015
4-nitrophenyl
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1016
2-trifluoro-
Me
H
H
H
2,6-dimethyl-4-(hepta-

methylphenyl

fluoroisopropyl)phenyl

1017
4-trifluoro-
Me
H
H
H
2,6-dimethyl-4-(hepta-

methylphenyl

fluoroisopropyl)phenyl

1018
4-trifluoro-
Me
H
H
H
2,6-dimethyl-4-(hepta-

methoxyphenyl

fluoroisopropyl)phenyl

1019
2,3-difluoro-
Me
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1020
2,4-difluoro-
Me
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1021
2,5-difluoro-
Me
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1022
2,6-difluoro-
Me
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1023
2,4-dichloro-
Me
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1024
2,6-dichloro-
Me
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1025
3,4-dichloro-
Me
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1026
2-chloro-4-
Me
H
H
H
2,6-dimethyl-4-(hepta-

nitrophenyl

fluoroisopropyl)phenyl

1027
2-chloro-4-
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluorophenyl

fluoroisopropyl)phenyl

1028
2-chloro-6-
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluorophenyl

fluoroisopropyl)phenyl

1029
4-chloro-2-
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluorophenyl

fluoroisopropyl)phenyl

1030
4-chloro-2-
Me
H
H
H
2,6-dimethyl-4-(hepta-

nitrophenyl

fluoroisopropyl)phenyl

1031
2,3,6-trifluoro
Me
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1032
3-(acetylamino)
Me
H
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1033
pyridine-2-yl
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1034
pyridine-3-yl
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1035
2-fluoropyr-
Me
H
H
H
2,6-dimethyl-4-(hepta-

idine-3-yl

fluoroisopropyl)phenyl

1036
2-chloropyr-
Me
H
H
H
2,6-dimethyl-4-(hepta-

idine-3-yl

fluoroisopropyl)phenyl

1037
2-chloropyr-
Me
H
H
H
2,6-dimethyl-4-(hepta-

idine-5-yl

fluoroisopropyl)phenyl

1038
2-trifluoro-
Me
H
H
H
2,6-dimethyl-4-(hepta-

methylpyr-

fluoroisopropyl)phenyl

idine-3-yl

1039
2-methylthio
Me
H
H
H
2,6-dimethyl-4-(hepta-

pyridine-3-yl

fluoroisopropyl)phenyl

1040
pyrazine-2-yl
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1041
furan-2-yl
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1042
furan-3-yl
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1043
2-tetrahydro-
Me
H
H
H
2,6-dimethyl-4-(hepta-

furanyl

fluoroisopropyl)phenyl

1044
benzofuran-2-yl
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1045
thiophene-2-yl
Me
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1046
phenyl
Me
H
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfony)phenyl

1047
2-methylphenyl
Me
H
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfony)phenyl

1048
4-methylphenyl
Me
H
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfony)phenyl

1049
2-fluorophenyl
Me
H
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfony)phenyl

1050
3-fluorophenyl
Me
H
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfony)phenyl

1051
4-fluorophenyl
Me
H
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfony)phenyl

1052
2-chlorophenyl
Me
H
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfony)phenyl

1053
4-chlorophenyl
Me
H
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfony)phenyl

1054
2-bromophenyl
Me
H
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfony)phenyl

1055
2-iodophenyl
Me
H
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfony)phenyl

1056
3-cyanophenyl
Me
H
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfony)phenyl

1057
4-cyanophenyl
Me
H
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfony)phenyl

1058
2-nitrophenyl
Me
H
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfony)phenyl

1059
3-nitrophenyl
Me
H
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfony)phenyl

1060
4-nitrophenyl
Me
H
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfony)phenyl

1061
2-trifluoro-
Me
H
H
H
2-bromo-4-(hepta-

methylphenyl

fluoroisopropyl)-6-

(methylsulfony)phenyl

1062
4-trifluoro-
Me
H
H
H
2-bromo-4-(hepta-

methylphenyl

fluoroisopropyl)-6-

(methylsulfony)phenyl

1063
4-trifluoro-
Me
H
H
H
2-bromo-4-(hepta-

methoxyphenyl

fluoroisopropyl)-6-

(methylsulfony)phenyl

1064
2,3-difluoro-
Me
H
H
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfony)phenyl

1065
2,4-difluoro-
Me
H
H
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfony)phenyl

1066
2,5-difluoro-
Me
H
H
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfony)phenyl

1067
2,6-difluoro-
Me
H
H
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfony)phenyl

1068
2,4-dichloro-
Me
H
H
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfony)phenyl

1069
2,6-dichloro-
Me
H
H
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfony)phenyl

1070
3,4-dichloro-
Me
H
H
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfony)phenyl

1071
2-chloro-4-
Me
H
H
H
2-bromo-4-(hepta-

nitrophenyl

fluoroisopropyl)-6-

(methylsulfony)phenyl

1072
2-chloro-4-
Me
H
H
H
2-bromo-4-(hepta-

fluorophenyl

fluoroisopropyl)-6-

(methylsulfony)phenyl

1073
2-chloro-6-
Me
H
H
H
2-bromo-4-(hepta-

fluorophenyl

fluoroisopropyl)-6-

(methylsulfony)phenyl

1074
4-chloro-2-
Me
H
H
H
2-bromo-4-(hepta-

fluorophenyl

fluoroisopropyl)-6-

(methylsulfony)phenyl

1075
4-chloro-2-
Me
H
H
H
2-bromo-4-(hepta-

nitrophenyl

fluoroisopropyl)-6-

(methylsulfony)phenyl

1076
2,3,6-trifluoro
Me
H
H
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfony)phenyl

1077
pyridine-2-yl
Me
H
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfony)phenyl

1078
pyridine-3-yl
Me
H
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfony)phenyl

1079
2-fluoropyr-
Me
H
H
H
2-bromo-4-(hepta-

idine-3-yl

fluoroisopropyl)-6-

(methylsulfony)phenyl

1080
2-chloropyr-
Me
H
H
H
2-bromo-4-(hepta-

idine-3-yl

fluoroisopropyl)-6-

(methylsulfony)phenyl

1081
2-chloropyr-
Me
H
H
H
2-bromo-4-(hepta-

idine-5-yl

fluoroisopropyl)-6-

(methylsulfony)phenyl

1082
2-methylthio
Me
H
H
H
2-bromo-4-(hepta-

pyridine-3-yl

fluoroisopropyl)-6-

(methylsulfony)phenyl

1083
pyrazine-2-yl
Me
H
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfony)phenyl

1084
furan-2-yl
Me
H
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfony)phenyl

1085
thiophene-2-yl
Me
H
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfony)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-trifluoro-
Me
H
H
H
2-n-propyl-6-iodo-4-

methylphenyl

(heptafluoroisopropyl)

phenyl

1102
4-trifluoro-
Me
H
H
H
2-n-propyl-6-iodo-4-

methylphenyl

(heptafluoroisopropyl)

phenyl

1103
4-trifluoro-
Me
H
H
H
2-n-propyl-6-iodo-4-

methoxyphenyl

(heptafluoroisopropyl)

phenyl

1104
2,3-difluoro-
Me
H
H
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1105
2,4-difluoro-
Me
H
H
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1106
2,5-difluoro-
Me
H
H
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1107
2,6-difluoro-
Me
H
H
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1108
2,4-dichloro-
Me
H
H
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1109
2,6-dichloro-
Me
H
H
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1110
3,4-dichloro-
Me
H
H
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1111
2-chloro-4-
Me
H
H
H
2-n-propyl-6-iodo-4-

nitrophenyl

(heptafluoroisopropyl)

phenyl

1112
2-chloro-4-
Me
H
H
H
2-n-propyl-6-iodo-4-

fluorophenyl

(heptafluoroisopropyl)

phenyl

1113
2-chloro-6-
Me
H
H
H
2-n-propyl-6-iodo-4-

fluorophenyl

(heptafluoroisopropyl)

phenyl

1114
4-chloro-2-
Me
H
H
H
2-n-propyl-6-iodo-4-

fluorophenyl

(heptafluoroisopropyl)

phenyl

1115
4-chloro-2-
Me
H
H
H
2-n-propyl-6-iodo-4-

nitrophenyl

(heptafluoroisopropyl)

phenyl

1116
2,3,6-trifluoro
Me
H
H
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1117
pyridine-2-yl
Me
H
H
H
2-n-propyl-6-iodo-4-

(heptafluoroisopropyl)

phenyl

1118
pyridine-3-yl
Me
H
H
H
2-n-propyl-6-iodo-4-

(heptafluoroisopropyl)

phenyl

1119
2-fluoropyr-
Me
H
H
H
2-n-propyl-6-iodo-4-

idine-3-yl

(heptafluoroisopropyl)

phenyl

1120
2-chloropyr-
Me
H
H
H
2-n-propyl-6-iodo-4-

idine-3-yl

(heptafluoroisopropyl)

phenyl

1121
2-chloropyr
Me
H
H
H
2-n-propyl-6-iodo-4-

idine-5-yl

(heptafluoroisopropyl)

phenyl

1122
2-methylthio
Me
H
H
H
2-n-propyl-6-iodo-4-

pyridine-3-yl

(heptafluoroisopropyl)

phenyl

1123
pyrazine-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-(hepta-

fluoro-n-propylthio)

phenyl

1126
phenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1127
2-methylphenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1128
4-methylphenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1129
2-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1130
3-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1131
4-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1132
2-chlorophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1133
4-chlorophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1134
2-bromophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1135
2-iodophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1136
3-cyanophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1137
4-cyanophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1138
2-nitrophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1139
3-nitrophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1140
4-nitrophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1141
2-trifluoro-
Me
H
H
H
2,6-dibromo-4-(hepta-

methylphenyl

fluoro-n-propylthio)

phenyl

1142
4-trifluoro-
Me
H
H
H
2,6-dibromo-4-(hepta-

methylphenyl

fluoro-n-propylthio)

phenyl

1143
4-trifluoro-
Me
H
H
H
2,6-dibromo-4-(hepta-

methoxyphenyl

fluoro-n-propylthio)

phenyl

1144
2,3-difluoro-
Me
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1145
2,4-difluoro-
Me
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1146
2,5-difluoro-
Me
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1147
2,6-difluoro-
Me
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1148
2,4-dichloro-
Me
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1149
2,6-dichloro-
Me
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1150
3,4-dichloro-
Me
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1151
2-chloro-4-
Me
H
H
H
2,6-dibromo-4-(hepta-

nitrophenyl

fluoro-n-propylthio)

phenyl

1152
2-chloro-4-
Me
H
H
H
2,6-dibromo-4-(hepta-

fluorophenyl

fluoro-n-propylthio)

phenyl

1153
2-chloro-6-
Me
H
H
H
2,6-dibromo-4-(hepta-

fluorophenyl

fluoro-n-propylthio)

phenyl

1154
4-chloro-2-
Me
H
H
H
2,6-dibromo-4-(hepta-

fluorophenyl

fluoro-n-propylthio)

phenyl

1155
4-chloro-2-
Me
H
H
H
2,6-dibromo-4-(hepta-

nitrophenyl

fluoro-n-propylthio)

phenyl

1156
2,3,6-trifluoro
Me
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1157
pyridine-2-yl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1158
pyridine-3-yl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1159
2-fluoropyr-
Me
H
H
H
2,6-dibromo-4-(hepta-

idine-3-yl

fluoro-n-propylthio)

phenyl

1160
2-chloropyr-
Me
H
H
H
2,6-dibromo-4-(hepta-

idine-3-yl

fluoro-n-propylthio)

phenyl

1161
2-chloropyr-
Me
H
H
H
2,6-dibromo-4-(hepta-

idine-5-yl

fluoro-n-propylthio)

phenyl

1162
2-methylthio
Me
H
H
H
2,6-dibromo-4-(hepta-

pyridine-3-yl

fluoro-n-propylthio)

phenyl

1163
pyrazine-2-yl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1164
furan-2-yl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1165
thiophene-2-yl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1166
phenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1167
2-methylphenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1168
4-methylphenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1169
2-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1170
3-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1171
4-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1172
2-chlorophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1173
4-chlorophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1174
2-bromophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1175
2-iodophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1176
3-cyanophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1177
4-cyanophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1178
2-nitrophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1179
3-nitrophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1180
4-nitrophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1181
2-trifluoro-
Me
H
H
H
2,6-dibromo-4-(hepta-

methylphenyl

fluoro-n-propylthio)

phenyl

1182
4-trifluoro-
Me
H
H
H
2,6-dibromo-4-(hepta-

methylphenyl

fluoro-n-propylthio)

phenyl

1183
4-trifluoro-
Me
H
H
H
2,6-dibromo-4-(hepta-

methoxyphenyl

fluoro-n-propylthio)

phenyl

1184
2,3-difluoro-
Me
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1185
2,4-difluoro-
Me
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1186
2,5-difluoro-
Me
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1187
2,6-difluoro-
Me
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1188
2,4-dichloro-
Me
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1189
2,6-dichloro-
Me
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1190
3,4-dichloro-
Me
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1191
2-chloro-4-
Me
H
H
H
2,6-dibromo-4-(hepta-

nitrophenyl

fluoro-n-propylthio)

phenyl

1192
2-chloro-4-
Me
H
H
H
2,6-dibromo-4-(hepta-

fluorophenyl

fluoro-n-propylthio)

phenyl

1193
2-chloro-6-
Me
H
H
H
2,6-dibromo-4-(hepta-

fluorophenyl

fluoro-n-propylthio)

phenyl

1194
4-chloro-2-
Me
H
H
H
2,6-dibromo-4-(hepta-

fluorophenyl

fluoro-n-propylthio)

phenyl

1195
4-chloro-2-
Me
H
H
H
2,6-dibromo-4-(hepta-

nitrophenyl

fluoro-n-propylthio)

phenyl

1196
2,3,6-trifluoro
Me
H
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1197
pyridine-2-yl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1198
pyridine-3-yl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1199
2-fluoropyr-
Me
H
H
H
2,6-dibromo-4-(hepta-

idine-3-yl

fluoro-n-propylthio)

phenyl

1200
2-chloropyr-
Me
H
H
H
2,6-dibromo-4-(hepta-

idine-3-yl

fluoro-n-propylthio)

phenyl

1201
2-chloropyr-
Me
H
H
H
2,6-dibromo-4-(hepta-

idine-5-yl

fluoro-n-propylthio)

phenyl

1202
2-methylthio
Me
H
H
H
2,6-dibromo-4-(hepta-

pyridine-3-yl

fluoro-n-propylthio)

phenyl

1203
pyrazine-2-yl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1204
furan-2-yl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1205
thiophene-2-yl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1206
2-fluorophenyl
Et
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1207
pyridine-3-yl
Et
H
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1208
phenyl
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1209
2-methylphenyl
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1210
3-methylphenyl
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1211
4-methylphenyl
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1212
2-nitrophenyl
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1213
3-nitrophenyl
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1214
4-nitrophenyl
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1215
2-cyanophenyl
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1216
3-cyanophenyl
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1217
4-cyanophenyl
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1218
2-fluorophenyl
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1219
3-fluorophenyl
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1220
4-fluorophenyl
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1221
2-chlorophenyl
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1222
4-chlorophenyl
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1223
2-bromophenyl
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1224
2-iodophenyl
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1225
2-trifluoro-
Me
H
F
H
2,6-dimethyl-4-(hepta-

methylphenyl

fluoroisopropyl)phenyl

1226
4-trifluoro-
Me
H
F
H
2,6-dimethyl-4-(hepta-

methylphenyl

fluoroisopropyl)phenyl

1227
4-trifluoro-
Me
H
F
H
2,6-dimethyl-4-(hepta-

methoxyphenyl

fluoroisopropyl)phenyl

1228
2,3-difluoro-
Me
H
F
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1229
2,4-difluoro-
Me
H
F
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1230
2,5-difluoro-
Me
H
F
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1231
2,6-difluoro-
Me
H
F
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1232
2,4-dichloro-
Me
H
F
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1233
2,6-dichloro-
Me
H
F
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1234
3,4-dichloro-
Me
H
F
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1235
2-fluoro-4-
Me
H
F
H
2,6-dimethyl-4-(hepta-

nitrophenyl

fluoroisopropyl)phenyl

1236
4-fluoro-2-
Me
H
F
H
2,6-dimethyl-4-(hepta-

nitrophenyl

fluoroisopropyl)phenyl

1237
2-chloro-4-
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluorophenyl

fluoroisopropyl)phenyl

1238
4-chloro-2-
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluorophenyl

fluoroisopropyl)phenyl

1239
2-chloro-6-
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluorophenyl

fluoroisopropyl)phenyl

1240
2-chloro-4-
Me
H
F
H
2,6-dimethyl-4-(hepta-

nitrophenyl

fluoroisopropyl)phenyl

1241
4-chloro-2-
Me
H
F
H
2,6-dimethyl-4-(hepta-

nitrophenyl

fluoroisopropyl)phenyl

1242
2,3,6-trifluoro
Me
H
F
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1243
pyridine-2-yl
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1244
pyridine-3-yl
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1245
2-chloropyr-
Me
H
F
H
2,6-dimethyl-4-(hepta-

idine-3-yl

fluoroisopropyl)phenyl

1246
2-fluoropyr-
Me
H
F
H
2,6-dimethyl-4-(hepta-

idine-3-yl

fluoroisopropyl)phenyl

1247
2-chloropyr-
Me
H
F
H
2,6-dimethyl-4-(hepta-

idine-5-yl

fluoroisopropyl)phenyl

1248
2-methylthio
Me
H
F
H
2,6-dimethyl-4-(hepta-

pyridine-3-yl

fluoroisopropyl)phenyl

1249
pyrazine-2-yl
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1250
furan-2-yl
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1251
furan-3-yl
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1252
2-tetrahydro-
Me
H
F
H
2,6-dimethyl-4-(hepta-

furanyl

fluoroisopropyl)phenyl

1253
benzofuran-2-
Me
H
F
H
2,6-dimethyl-4-(hepta-

yl

fluoroisopropyl)phenyl

1254
thiophene-2-yl
Me
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1255
phenyl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1256
2-methylphenyl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1257
3-methylphenyl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1258
4-methylphenyl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1259
2-nitrophenyl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1260
3-nitrophenyl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1261
4-nitrophenyl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1262
2-cyanophenyl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1263
3-cyanophenyl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1264
4-cyanophenyl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1265
2-fluorophenyl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1266
3-fluorophenyl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1267
4-fluorophenyl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1268
2-chlorophenyl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1269
4-chlorophenyl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1270
2-bromophenyl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1271
2-iodophenyl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1272
2-trifluoro-
Me
H
F
H
2,6-dimethyl-4-(nona-

methylphenyl

fluoro-2-butyl)phenyl

1273
4-trifluoro-
Me
H
F
H
2,6-dimethyl-4-(nona-

methylphenyl

fluoro-2-butyl)phenyl

1274
4-trifluoro-
Me
H
F
H
2,6-dimethyl-4-(nona-

methoxyphenyl

fluoro-2-butyl)phenyl

1275
2,3-difluoro-
Me
H
F
H
2,6-dimethyl-4-(nona-

phenyl

fluoro-2-butyl)phenyl

1276
2,4-difluoro-
Me
H
F
H
2,6-dimethyl-4-(nona-

phenyl

fluoro-2-butyl)phenyl

1277
2,5-difluoro-
Me
H
F
H
2,6-dimethyl-4-(nona-

phenyl

fluoro-2-butyl)phenyl

1278
2,6-difluoro-
Me
H
F
H
2,6-dimethyl-4-(nona-

phenyl

fluoro-2-butyl)phenyl

1279
2,4-dichloro-
Me
H
F
H
2,6-dimethyl-4-(nona-

phenyl

fluoro-2-butyl)phenyl

1280
2,6-dichloro-
Me
H
F
H
2,6-dimethyl-4-(nona-

phenyl

fluoro-2-butyl)phenyl

1281
3,4-dichloro-
Me
H
F
H
2,6-dimethyl-4-(nona-

phenyl

fluoro-2-butyl)phenyl

1282
2-fluoro-4-
Me
H
F
H
2,6-dimethyl-4-(nona-

nitrophenyl

fluoro-2-butyl)phenyl

1283
4-fluoro-2-
Me
H
F
H
2,6-dimethyl-4-(nona-

nitrophenyl

fluoro-2-butyl)phenyl

1284
2-chloro-4-
Me
H
F
H
2,6-dimethyl-4-(nona-

fluorophenyl

fluoro-2-butyl)phenyl

1285
4-chloro-2-
Me
H
F
H
2,6-dimethyl-4-(nona-

fluorophenyl

fluoro-2-butyl)phenyl

1286
2-chloro-6-
Me
H
F
H
2,6-dimethyl-4-(nona-

fluorophenyl

fluoro-2-butyl)phenyl

1287
2-chloro-4-
Me
H
F
H
2,6-dimethyl-4-(nona-

nitrophenyl

fluoro-2-butyl)phenyl

1288
4-chloro-2-
Me
H
F
H
2,6-dimethyl-4-(nona-

nitrophenyl

fluoro-2-butyl)phenyl

1289
2,3,6-trifluoro
Me
H
F
H
2,6-dimethyl-4-(nona-

phenyl

fluoro-2-butyl)phenyl

1290
pyridine-2-yl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1291
pyridine-3-yl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1292
2-fluoropyr-
Me
H
F
H
2,6-dimethyl-4-(nona-

idine-3-yl

fluoro-2-butyl)phenyl

1293
2-chloropyr-
Me
H
F
H
2,6-dimethyl-4-(nona-

idine-3-yl

fluoro-2-butyl)phenyl

1294
2-chloropyr-
Me
H
F
H
2,6-dimethyl-4-(nona-

idine-5-yl

fluoro-2-butyl)phenyl

1295
2-methylthio
Me
H
F
H
2,6-dimethyl-4-(nona-

pyridine-3-yl

fluoro-2-butyl)phenyl

1296
pyrazine-2-yl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1297
furan-2-yl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1298
furan-3-yl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1299
2-tetrahydro-
Me
H
F
H
2,6-dimethyl-4-(nona-

furanyl

fluoro-2-butyl)phenyl

1300
benzofuran-2-yl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1301
thiophene-2-yl
Me
H
F
H
2,6-dimethyl-4-(nona-

fluoro-2-butyl)phenyl

1302
phenyl
Me
H
F
H
2-bromo-4-(hepta-

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1303
2-methylphenyl
Me
H
F
H
2-bromo-4-(hepta-

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1304
4-methylphenyl
Me
H
F
H
2-bromo-4-(hepta-

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1305
2-fluorophenyl
Me
H
F
H
2-bromo-4-(hepta-

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1306
3-fluorophenyl
Me
H
F
H
2-bromo-4-(hepta-

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1307
4-fluorophenyl
Me
H
F
H
2-bromo-4-(hepta-

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1308
2-chlorophenyl
Me
H
F
H
2-bromo-4-(hepta-

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1309
4-chlorophenyl
Me
H
F
H
2-bromo-4-(hepta-

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1310
2-bromophenyl
Me
H
F
H
2-bromo-4-(hepta-

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1311
2-iodophenyl
Me
H
F
H
2-bromo-4-(hepta-

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1312
3-cyanophenyl
Me
H
F
H
2-bromo-4-(hepta-

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1313
4-cyanophenyl
Me
H
F
H
2-bromo-4-(hepta-

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1314
2-nitrophenyl
Me
H
F
H
2-bromo-4-(hepta-

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1315
3-nitrophenyl
Me
H
F
H
2-bromo-4-(hepta-

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1316
4-nitrophenyl
Me
H
F
H
2-bromo-4-(hepta-

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1317
2-trifluoro
Me
H
F
H
2-bromo-4-(hepta-

methylphenyl

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1318
4-trifluoro-
Me
H
F
H
2-bromo-4-(hepta-

methylphenyl

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1319
4-trifluoro-
Me
H
F
H
2-bromo-4-(hepta-

methoxyphenyl

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1320
2,3-difluoro-
Me
H
F
H
2-bromo-4-(hepta-

phenyl

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1321
2,4-difluoro-
Me
H
F
H
2-bromo-4-(hepta-

phenyl

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1322
2,5-difluoro-
Me
H
F
H
2-bromo-4-(hepta-

phenyl

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1323
2,6-difluoro-
Me
H
F
H
2-bromo-4-(hepta-

phenyl

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1324
2,4-dichloro-
Me
H
F
H
2-bromo-4-(hepta-

phenyl

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1325
2,6-dichloro-
Me
H
F
H
2-bromo-4-(hepta-

phenyl

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1326
3,4-dichloro-
Me
H
F
H
2-bromo-4-(hepta-

phenyl

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1327
2-chloro-4-
Me
H
F
H
2-bromo-4-(hepta-

nitrophenyl

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1328
2-chloro-4-
Me
H
F
H
2-bromo-4-(hepta-

fluorophenyl

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1329
2-chloro-6-
Me
H
F
H
2-bromo-4-(hepta-

fluorophenyl

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1330
4-chloro-2-
Me
H
F
H
2-bromo-4-(hepta-

fluorophenyl

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1331
4-chloro-2-
Me
H
F
H
2-bromo-4-(hepta-

nitrophenyl

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1332
2,3,6-trifluoro
Me
H
F
H
2-bromo-4-(hepta-

phenyl

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1333
pyridine-2-yl
Me
H
F
H
2-bromo-4-(hepta-

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1334
pyridine-3-yl
Me
H
F
H
2-bromo-4-(hepta-

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1335
2-fluoropyr-
Me
H
F
H
2-bromo-4-(hepta-

idine-3-yl

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1336
2-chloropyr-
Me
H
F
H
2-bromo-4-(hepta-

idine-3-yl

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1337
2-chloropyr-
Me
H
F
H
2-bromo-4-(hepta-

idine-5-yl

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1338
2-methylthio
Me
H
F
H
2-bromo-4-(hepta-

pyridine-3-yl

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1339
pyrazine-2-yl
Me
H
F
H
2-bromo-4-(hepta-

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1340
furan-2-yl
Me
H
F
H
2-bromo-4-(hepta-

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1341
thiophene-2-yl
Me
H
F
H
2-bromo-4-(hepta-

fluoroiosopropyl)-6-

(methylsulfonyl)

phenyl

1342
phenyl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1343
2-methylphenyl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1344
4-methylphenyl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1345
2-fluorophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1346
3-fluorophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1347
4-fluorophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1348
2-chlorophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1349
4-chlorophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1350
2-bromophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1351
2-iodophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1352
3-cyanophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1353
4-cyanophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1354
2-nitrophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1355
3-nitrophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1356
4-nitrophenyl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1357
2-trifluoro-
Me
H
F
H
2-n-propyl-6-iodo-4-

methylphenyl

(heptafluoroiso-

propyl)phenyl

1358
4-trifluoro-
Me
H
F
H
2-n-propyl-6-iodo-4-

methylphenyl

(heptafluoroiso-

propyl)phenyl

1359
4-trifluoro-
Me
H
F
H
2-n-propyl-6-iodo-4-

methoxyphenyl

(heptafluoroiso-

propyl)phenyl

1360
2,3-difluoro
Me
H
F
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroiso-

propyl)phenyl

1361
2,4-difluoro-
Me
H
F
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroiso-

propyl)phenyl

1362
2,5-difluoro-
Me
H
F
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroiso-

propyl)phenyl

1363
2,6-difluoro-
Me
H
F
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroiso-

propyl)phenyl

1364
2,4-dichloro-
Me
H
F
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroiso-

propyl)phenyl

1365
2,6-dichloro-
Me
H
F
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroiso-

propyl)phenyl

1366
3,4-dichloro-
Me
H
F
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroiso-

propyl)phenyl

1367
2-chloro-4-
Me
H
F
H
2-n-propyl-6-iodo-4-

nitrophenyl

(heptafluoroiso-

propyl)phenyl

1368
2-chloro-4-
Me
H
F
H
2-n-propyl-6-iodo-4-

fluorophenyl

(heptafluoroiso-

propyl)phenyl

1369
2-chloro-6-
Me
H
F
H
2-n-propyl-6-iodo-4-

fluorophenyl

(heptafluoroiso-

propyl)phenyl

1370
4-chloro-2-
Me
H
F
H
2-n-propyl-6-iodo-4-

fluorophenyl

(heptafluoroiso-

propyl)phenyl

1371
4-chloro-2-
Me
H
F
H
2-n-propyl-6-iodo-4-

nitrophenyl

(heptafluoroiso-

propyl)phenyl

1372
2,3,6-trifluoro
Me
H
F
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroiso-

propyl)phenyl

1373
pyridine-2-yl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1374
pyridine-3-yl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1375
2-fluoropyr-
Me
H
F
H
2-n-propyl-6-iodo-4-

idine-3-yl

(heptafluoroiso-

propyl)phenyl

1376
2-chloropyr-
Me
H
F
H
2-n-propyl-6-iodo-4-

idine-3-yl

(heptafluoroiso-

propyl)phenyl

1377
2-chloropyr-
Me
H
F
H
2-n-propyl-6-iodo-4-

idine-5-yl

(heptafluoroiso-

propyl)phenyl

1378
2-methylthio
Me
H
F
H
2-n-propyl-6-iodo-4-

pyridine-3-yl

(heptafluoroiso-

propyl)phenyl

1379
pyrazine-2-yl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1380
furan-2-yl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1381
thiophene-2-yl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1382
phenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

flouro-n-propylthio)

phenyl

1383
2-methylphenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

flouro-n-propylthio)

phenyl

1384
4-methylphenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

flouro-n-propylthio)

phenyl

1385
2-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

flouro-n-propylthio)

phenyl

1386
3-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

flouro-n-propylthio)

phenyl

1387
4-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

flouro-n-propylthio)

phenyl

1388
2-chlorophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

flouro-n-propylthio)

phenyl

1389
4-chlorophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

flouro-n-propylthio)

phenyl

1390
2-bromophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

flouro-n-propylthio)

phenyl

1391
2-iodophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

flouro-n-propylthio)

phenyl

1392
3-cyanophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

flouro-n-propylthio)

phenyl

1393
4-cyanophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

flouro-n-propylthio)

phenyl

1394
2-nitrophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

flouro-n-propylthio)

phenyl

1395
3-nitrophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

flouro-n-propylthio)

phenyl

1396
4-nitrophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

flouro-n-propylthio)

phenyl

1397
phenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

flouro-n-propylthio)

phenyl

1398
4-trifluoro-
Me
H
F
H
2,6-dibromo-4-(hepta-

methylphenyl

flouro-n-propylthio)

phenyl

1399
4-trifluoro-
Me
H
F
H
2,6-dibromo-4-(hepta-

methoxyphenyl

flouro-n-propylthio)

phenyl

1400
2,3-difluoro-
Me
H
F
H
2,6-dibromo-4-(hepta-

phenyl

flouro-n-propylthio)

phenyl

1401
2,4-difluoro-
Me
H
F
H
2,6-dibromo-4-(hepta-

phenyl

flouro-n-propylthio)

propyl)phenyl

1402
2,5-difluoro-
Me
H
F
H
2,6-dibromo-4-(hepta-

phenyl

flouro-n-propylthio)

propyl)phenyl

1403
2,6-difluoro-
Me
H
F
H
2,6-dibromo-4-(hepta-

phenyl

flouro-n-propylthio)

propyl)phenyl

1404
2,4-dichloro-
Me
H
F
H
2,6-dibromo-4-(hepta-

phenyl

flouro-n-propylthio)

propyl)phenyl

1405
2,6-dichloro-
Me
H
F
H
2,6-dibromo-4-(hepta-

phenyl

flouro-n-propylthio)

propyl)phenyl

1406
3,4-dichloro-
Me
H
F
H
2,6-dibromo-4-(hepta-

phenyl

flouro-n-propylthio)

propyl)phenyl

1407
2-chloro-4-
Me
H
F
H
2,6-dibromo-4-(hepta-

nitrophenyl

flouro-n-propylthio)

propyl)phenyl

1408
2-chloro-4-
Me
H
F
H
2,6-dibromo-4-(hepta-

fluorophenyl

flouro-n-propylthio)

propyl)phenyl

1409
2-chloro-6-
Me
H
F
H
2,6-dibromo-4-(hepta-

fluorophenyl

flouro-n-propylthio)

propyl)phenyl

1410
4-chloro-2-
Me
H
F
H
2,6-dibromo-4-(hepta-

fluorophenyl

flouro-n-propylthio)

propyl)phenyl

1411
4-chloro-2-
Me
H
F
H
2,6-dibromo-4-(hepta-

nitrophenyl

flouro-n-propylthio)

propyl)phenyl

1412
2,3,6-trifluoro
Me
H
F
H
2,6-dibromo-4-(hepta-

phenyl

flouro-n-propylthio)

propyl)phenyl

1413
pyridine-2-yl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1414
pyridine-3-yl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1415
2-fluoropyr-
Me
H
F
H
2,6-dibromo-4-(hepta-

idine-3-yl

flouro-n-propylthio)

propyl)phenyl

1416
2-chloropyr-
Me
H
F
H
2,6-dibromo-4-(hepta-

idine-3-yl

flouro-n-propylthio)

propyl)phenyl

1417
2-chloropyr-
Me
H
F
H
2,6-dibromo-4-(hepta-

idine-5-yl

flouro-n-propylthio)

propyl)phenyl

1418
2-methylthio
Me
H
F
H
2,6-dibromo-4-(hepta-

pyridine-3-yl

flouro-n-propylthio)

propyl)phenyl

1419
pyrazine-2-yl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1420
furan-2-yl
Me
H
F
H
2-n-propyl-6-iodo-4-

(heptafluoroiso-

propyl)phenyl

1421
thiophene-2-yl
Me
H
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1422
phenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1423
2-methylphenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1424
4-methylphenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1425
2-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1426
3-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1427
4-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1428
2-chlorophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1429
4-chlorophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1430
2-bromophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1431
2-iodophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1432
3-cyanophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1433
4-cyanophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1434
2-nitrophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1435
3-nitrophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1436
4-nitrophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1437
2-trifluoro-
Me
H
F
H
2,6-dibromo-4-(hepta-

methylphenyl

fluoro-n-propylsul-

finyl)phenyl

1438
4-trifluoro-
Me
H
F
H
2,6-dibromo-4-(hepta-

methylphenyl

fluoro-n-propylsul-

finyl)phenyl

1439
4-trifluoro-
Me
H
F
H
2,6-dibromo-4-(hepta-

methoxyphenyl

fluoro-n-propylsul-

finyl)phenyl

1440
2,3-difluoro-
Me
H
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

1441
2,4-difluoro-
Me
H
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

1442
2,5-difluoro-
Me
H
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

1443
2,6-difluoro-
Me
H
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

1444
2,4-dichloro-
Me
H
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

1445
2,6-dichloro-
Me
H
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

1446
3,4-dichloro-
Me
H
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

1447
2-chloro-4-
Me
H
F
H
2,6-dibromo-4-(hepta-

nitrophenyl

fluoro-n-propylsul-

finyl)phenyl

1448
2-chloro-4-
Me
H
F
H
2,6-dibromo-4-(hepta-

fluorophenyl

fluoro-n-propylsul-

finyl)phenyl

1449
2-chloro-6-
Me
H
F
H
2,6-dibromo-4-(hepta-

fluorophenyl

fluoro-n-propylsul-

finyl)phenyl

1450
4-chloro-2-
Me
H
F
H
2,6-dibromo-4-(hepta-

fluorophenyl

fluoro-n-propylsul-

finyl)phenyl

1451
4-chloro-2-
Me
H
F
H
2,6-dibromo-4-(hepta-

nitrophenyl

fluoro-n-propylsul-

finyl)phenyl

1452
2,3,6-trifluoro
Me
H
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

1453
pyridine-2-yl
Me
H
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1454
pyridine-3-yl
Me
H
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1455
2-fluoropyr-
Me
H
F
H
2,6-dibromo-4-(hepta-

idine-3-yl

fluoro-n-propylsul-

finyl)phenyl

1456
2-chloropyr-
Me
H
F
H
2,6-dibromo-4-(hepta-

idine-3-yl

fluoro-n-propylsul-

finyl)phenyl

1457
2-chloropyr-
Me
H
F
H
2,6-dibromo-4-(hepta-

idine-5-yl

fluoro-n-propylsul-

finyl)phenyl

1458
2-methylthio
Me
H
F
H
2,6-dibromo-4-(hepta-

pyridine-3-yl

fluoro-n-propylsul-

finyl)phenyl

1459
pyrazine-2-yl
Me
H
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1460
furan-2-yl
Me
H
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1461
thiophene-2-yl
Me
H
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1462
phenyl
Et
H
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1463
phenyl
Me
H
H
F
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1464
4-nitrophenyl
Me
H
H
F
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1465
4-cyanophenyl
Me
H
H
F
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1466
phenyl
Me
H
H
F
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1467
4-nitrophenyl
Me
H
H
F
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1468
4-cyanophenyl
Me
H
H
F
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1469
phenyl
Me
H
H
F
2-n-propyl-6-iodo-4-

(heptafluoroisopro-

pyl)phenyl

1470
4-nitrophenyl
Me
H
H
F
2-n-propyl-6-iodo-4-

(heptafluoroisopro-

pyl)phenyl

1471
4-cyanophenyl
Me
H
H
F
2-n-propyl-6-iodo-4-

(heptafluoroisopro-

pyl)phenyl

1472
phenyl
Me
H
H
F
2,6-dibromo-4-

(heptafluoro-n-pro-

pylthio)phenyl

1473
4-nitrophenyl
Me
H
H
F
2,6-dibromo-4-

(heptafluoro-n-pro-

pylthio)phenyl

1474
4-cyanophenyl
Me
H
H
F
2,6-dibromo-4-

(heptafluoro-n-pro-

pylthio)phenyl

1475
phenyl
Me
H
H
F
2,6-dibromo-4-

(heptafluoro-n-pro-

pylsulfonyl)phenyl

1476
4-nitrophenyl
Me
H
H
F
2,6-dibromo-4-

(heptafluoro-n-pro-

pylsulfonyl)phenyl

1477
4-cyanophenyl
Me
H
H
F
2,6-dibromo-4-

(heptafluoro-n-pro-

pylsulfonyl)phenyl

1478
phenyl
H
Me
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)

phenyl

1479
phenyl
H
Me
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

methyphenyl

1480
phenyl
H
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1481
2-fluorophenyl
H
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1482
phenyl
H
Et
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1483
phenyl
H
i-Pr
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1484
phenyl
H
acetyl
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1485
phenyl
H
Me
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1486
2-fluorophenyl
H
Me
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1487
phenyl
Me
Me
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1488
2-methylphenyl
Me
Me
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1489
4-methylphenyl
Me
Me
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1490
2-fluorophenyl
Me
Me
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1491
3-fluorophenyl
Me
Me
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1492
4-fluorophenyl
Me
Me
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1493
2-chlorophenyl
Me
Me
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1494
4-chlorophenyl
Me
Me
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1495
2-bromophenyl
Me
Me
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1496
2-iodophenyl
Me
Me
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1497
3-cyanophenyl
Me
Me
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1498
4-cyanophenyl
Me
Me
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1499
2-nitrophenyl
Me
Me
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1500
3-nitrophenyl
Me
Me
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1501
4-nitrophenyl
Me
Me
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1502
2-trifluoro-
Me
Me
H
H
2,6-dimethyl-4-(hepta-

methylphenyl

fluoroisopropyl)phenyl

1503
4-trifluoro-
Me
Me
H
H
2,6-dimethyl-4-(hepta-

methylphenyl

fluoroisopropyl)phenyl

1504
4-trifluoro-
Me
Me
H
H
2,6-dimethyl-4-(hepta-

methoxyphenyl

fluoroisopropyl)phenyl

1505
2,3-difluoro-
Me
Me
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1506
2,4-difluoro-
Me
Me
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1507
2,5-difluoro-
Me
Me
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1508
2,6-difluoro-
Me
Me
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1509
2,4-dichloro-
Me
Me
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1510
2,6-dichloro-
Me
Me
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1511
3,4-dichloro-
Me
Me
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1512
2-chloro-4-
Me
Me
H
H
2,6-dimethyl-4-(hepta-

nitrophenyl

fluoroisopropyl)phenyl

1513
2-chloro-4-
Me
Me
H
H
2,6-dimethyl-4-(hepta-

fluorophenyl

fluoroisopropyl)phenyl

1514
2-chloro-6-
Me
Me
H
H
2,6-dimethyl-4-(hepta-

fluorophenyl

fluoroisopropyl)phenyl

1515
4-chloro-2-
Me
Me
H
H
2,6-dimethyl-4-(hepta-

fluorophenyl

fluoroisopropyl)phenyl

1516
4-chloro-2-
Me
Me
H
H
2,6-dimethyl-4-(hepta-

nitrophenyl

fluoroisopropyl)phenyl

1517
2,3,6-trifluoro
Me
Me
H
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1518
pyridine-2-yl
Me
Me
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1519
pyridine-3-yl
Me
Me
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1520
2-fluoropyr-
Me
Me
H
H
2,6-dimethyl-4-(hepta-

idine-3-yl

fluoroisopropyl)phenyl

1521
2-chloropyr-
Me
Me
H
H
2,6-dimethyl-4-(hepta-

idine-3-yl

fluoroisopropyl)phenyl

1522
2-chloropyr-
Me
Me
H
H
2,6-dimethyl-4-(hepta-

idine-5-yl

fluoroisopropyl)phenyl

1522
2-methylthio
Me
Me
H
H
2,6-dimethyl-4-(hepta-

pyridine-3-yl

fluoroisopropyl)phenyl

1524
pyrazine-2-yl
Me
Me
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1525
furan-2-yl
Me
Me
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1526
thiophene-2-yl
Me
Me
H
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1527
phenyl
Me
Me
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1528
2-methylphenyl
Me
Me
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1529
4-methylphenyl
Me
Me
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1530
2-fluorophenyl
Me
Me
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1531
3-fluorophenyl
Me
Me
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1532
4-fluorophenyl
Me
Me
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1533
2-chlorophenyl
Me
Me
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1534
4-chlorophenyl
Me
Me
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1535
2-bromophenyl
Me
Me
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1536
2-iodophenyl
Me
Me
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1537
3-cyanophenyl
Me
Me
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1538
4-cyanophenyl
Me
Me
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1539
2-nitrophenyl
Me
Me
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1540
3-nitrophenyl
Me
Me
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1541
4-nitrophenyl
Me
Me
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1542
2-trifluoro-
Me
Me
H
H
2-bromo-4-(hepta-

methylphenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1543
4-trifluoro-
Me
Me
H
H
2-bromo-4-(hepta-

methylphenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1544
4-trifluoro-
Me
Me
H
H
2-bromo-4-(hepta-

methoxyphenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1545
2,3-difluoro-
Me
Me
H
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1546
2,4-difluoro-
Me
Me
H
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1547
2,5-difluoro-
Me
Me
H
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1548
2,6-difluoro-
Me
Me
H
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1549
2,4-dichloro-
Me
Me
H
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1550
2,6-dichloro-
Me
Me
H
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1551
3,4-dichloro-
Me
Me
H
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1552
2-chloro-4-
Me
Me
H
H
2-bromo-4-(hepta-

nitrophenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1553
2-chloro-4-
Me
Me
H
H
2-bromo-4-(hepta-

fluorophenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1554
2-chloro-6-
Me
Me
H
H
2-bromo-4-(hepta-

fluorophenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1555
4-chloro-2-
Me
Me
H
H
2-bromo-4-(hepta-

fluorophenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1556
4-chloro-2-
Me
Me
H
H
2-bromo-4-(hepta-

nitrophenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1557
2,3,6-trifluoro
Me
Me
H
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1558
pyridine-2-yl
Me
Me
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1559
pyridine-3-yl
Me
Me
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1560
2-fluoropyr-
Me
Me
H
H
2-bromo-4-(hepta-

idine-3-yl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1561
2-chloropyr-
Me
Me
H
H
2-bromo-4-(hepta-

idine-3-yl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1562
2-chloropyr-
Me
Me
H
H
2-bromo-4-(hepta-

idine-5-yl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1563
2-methylthio
Me
Me
H
H
2-bromo-4-(hepta-

pyridine-3-yl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1564
pyrazine-2-yl
Me
Me
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1565
furan-2-yl
Me
Me
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1566
thiophene-2-yl
Me
Me
H
H
2-bromo-4-(hepta-

fluoroisopropyl)-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-trifluoro-
Me
Me
H
H
2-n-propyl-6-iodo-4-

methylphenyl

(heptafluoroisopropyl)

phenyl

1583
4-trifluoro-
Me
Me
H
H
2-n-propyl-6-iodo-4-

methylphenyl

(heptafluoroisopropyl)

phenyl

1584
4-trifluoro-
Me
Me
H
H
2-n-propyl-6-iodo-4-

methoxyphenyl

(heptafluoroisopropyl)

phenyl

1585
2,3-difluoro-
Me
Me
H
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1586
2,4-difluoro-
Me
Me
H
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1587
2,5-difluoro-
Me
Me
H
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1588
2,6-difluoro-
Me
Me
H
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1589
2,4-dichloro-
Me
Me
H
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1590
2,6-dichloro-
Me
Me
H
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1591
3,4-dichloro-
Me
Me
H
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1592
2-chloro-4-
Me
Me
H
H
2-n-propyl-6-iodo-4-

nitrophenyl

(heptafluoroisopropyl)

phenyl

1593
2-chloro-4-
Me
Me
H
H
2-n-propyl-6-iodo-4-

fluorophenyl

(heptafluoroisopropyl)

phenyl

1594
2-chloro-6-
Me
Me
H
H
2-n-propyl-6-iodo-4-

fluorophenyl

(heptafluoroisopropyl)

phenyl

1595
4-chloro-2-
Me
Me
H
H
2-n-propyl-6-iodo-4-

fluorophenyl

(heptafluoroisopropyl)

phenyl

1596
4-chloro-2-
Me
Me
H
H
2-n-propyl-6-iodo-4-

nitrophenyl

(heptafluoroisopropyl)

phenyl

1597
2,3,6-trifluoro
Me
Me
H
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1598
pyridine-2-yl
Me
Me
H
H
2-n-propyl-6-iodo-4-

(heptafluoroisopropyl)

phenyl

1599
pyridine-3-yl
Me
Me
H
H
2-n-propyl-6-iodo-4-

(heptafluoroisopropyl)

phenyl

1600
2-fluoropyr-
Me
Me
H
H
2-n-propyl-6-iodo-4-

idine-3-yl

(heptafluoroisopropyl)

phenyl

1601
2-chloropyr-
Me
Me
H
H
2-n-propyl-6-iodo-4-

idine-3-yl

(heptafluoroisopropyl)

phenyl

1602
2-chloropyr-
Me
Me
H
H
2-n-propyl-6-iodo-4-

idine-5-yl

(heptafluoroisopropyl)

phenyl

1603
2-methylthio
Me
Me
H
H
2-n-propyl-6-iodo-4-

pyridine-3-yl

(heptafluoroisopropyl)

phenyl

1604
pyrazine-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
thiophene-2-yl
Me
Me
H
H
2-n-propyl-6-iodo-4-

(heptafluoroisopropyl)

phenyl

1607
phenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1608
2-methylphenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1609
3-methylphenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1610
4-methylphenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1611
2-nitrophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1612
3-nitrophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1613
4-nitrophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1614
2-cyanophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1615
3-cyanophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1616
4-cyanophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1617
2-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1618
3-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1619
4-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1620
2-chlorophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1621
4-chlorophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1622
2-bromophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1623
2-iodophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1624
2-trifluoro-
Me
Me
H
H
2,6-dibromo-4-(hepta-

methylphenyl

fluoro-n-propylthio)

phenyl

1625
4-trifluoro-
Me
Me
H
H
2,6-dibromo-4-(hepta-

methylphenyl

fluoro-n-propylthio)

phenyl

1626
4-trifluoro-
Me
Me
H
H
2,6-dibromo-4-(hepta-

methoxyphenyl

fluoro-n-propylthio)

phenyl

1627
2,3-difluoro-
Me
Me
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1628
2,4-difluoro-
Me
Me
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1629
2,5-difluoro-
Me
Me
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1630
2,6-difluoro-
Me
Me
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1631
2,4-dichloro-
Me
Me
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1632
2,6-dichloro-
Me
Me
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1633
3,4-dichloro-
Me
Me
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1634
2-fluoro-4-
Me
Me
H
H
2,6-dibromo-4-(hepta-

nitrophenyl

fluoro-n-propylthio)

phenyl

1635
4-fluoro-2-
Me
Me
H
H
2,6-dibromo-4-(hepta-

nitrophenyl

fluoro-n-propylthio)

phenyl

1636
2-chloro-4-
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluorophenyl

fluoro-n-propylthio)

phenyl

1637
4-chloro-2-
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluorophenyl

fluoro-n-propylthio)

phenyl

1638
2-chloro-6-
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluorophenyl

fluoro-n-propylthio)

phenyl

1639
2-chloro-4-
Me
Me
H
H
2,6-dibromo-4-(hepta-

nitrophenyl

fluoro-n-propylthio)

phenyl

1640
4-chloro-2-
Me
Me
H
H
2,6-dibromo-4-(hepta-

nitrophenyl

fluoro-n-propylthio)

phenyl

1641
2,3,6-trifluoro
Me
Me
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1642
pyridine-2-yl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1643
pyridine-3-yl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1644
2-fluoropyr-
Me
Me
H
H
2,6-dibromo-4-(hepta-

idine-3-yl

fluoro-n-propylthio)

phenyl

1645
2-chloropyri-
Me
Me
H
H
2,6-dibromo-4-(hepta-

dine-3-yl

fluoro-n-propylthio)

phenyl

1646
2-chloropyr-
Me
Me
H
H
2,6-dibromo-4-(hepta-

idine-5-yl

fluoro-n-propylthio)

phenyl

1647
2-methylthio
Me
Me
H
H
2,6-dibromo-4-(hepta-

pyridine-3-yl

fluoro-n-propylthio)

phenyl

1648
pyrazine-2-yl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1649
furan-2-yl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1650
furan-3-yl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1651
2-tetrahydro-
Me
Me
H
H
2,6-dibromo-4-(hepta-

furanyl

fluoro-n-propylthio)

phenyl

1652
benzofuran-2-yl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1653
thiophene-2-yl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1654
3,4-dinitro-
Me
Me
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1655
3-methoxy-4-
Me
Me
H
H
2,6-dibromo-4-(hepta-

nitrophenyl

fluoro-n-propylthio)

phenyl

1656
2,3,4-trifluoro
Me
Me
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1657
phenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1658
2-methylphenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1659
4-methylphenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1660
2-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1661
3-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1662
4-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1663
2-chlorophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1664
4-chlorophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1665
2-bromophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1666
2-iodophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1667
3-cyanophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1668
4-cyanophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1669
2-nitrophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1670
3-nitrophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1671
4-nitrophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1672
2-trifluoro-
Me
Me
H
H
2,6-dibromo-4-(hepta-

methylphenyl

fluoro-n-propylsul-

finyl)phenyl

1673
4-trifluoro-
Me
Me
H
H
2,6-dibromo-4-(hepta-

methylphenyl

fluoro-n-propylsul-

finyl)phenyl

1674
4-trifluoro-
Me
Me
H
H
2,6-dibromo-4-(hepta-

methoxyphenyl

fluoro-n-propylsul-

finyl)phenyl

1675
2,3-difluoro-
Me
Me
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

1676
2,4-difluoro-
Me
Me
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

1677
2,5-difluoro-
Me
Me
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

1678
2,6-difluoro-
Me
Me
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

1679
2,4-dichloro-
Me
Me
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

1680
2,6-dichloro-
Me
Me
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

1681
3,4-dichloro-
Me
Me
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

1682
2-chloro-4-
Me
Me
H
H
2,6-dibromo-4-(hepta-

nitrophenyl

fluoro-n-propylsul-

finyl)phenyl

1683
2-chloro-4-
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluorophenyl

fluoro-n-propylsul-

finyl)phenyl

1684
2-chloro-6-
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluorophenyl

fluoro-n-propylsul-

finyl)phenyl

1685
4-chloro-2-
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluorophenyl

fluoro-n-propylsul-

finyl)phenyl

1686
4-chloro-2-
Me
Me
H
H
2,6-dibromo-4-(hepta-

nitrophenyl

fluoro-n-propylsul-

finyl)phenyl

1687
2,3,6-trifluoro
Me
Me
H
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylsul-

finyl)phenyl

1688
pyridine-2-yl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1689
pyridine-3-yl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1690
2-fluoropyr-
Me
Me
H
H
2,6-dibromo-4-(hepta-

idine-3-yl

fluoro-n-propylsul-

finyl)phenyl

1691
2-chloropyr-
Me
Me
H
H
2,6-dibromo-4-(hepta-

idine-3-yl

fluoro-n-propylsul-

finyl)phenyl

1692
2-chloropyr-
Me
Me
H
H
2,6-dibromo-4-(hepta-

idine-5-yl

fluoro-n-propylsul-

finyl)phenyl

1693
2-methylthio
Me
Me
H
H
2,6-dibromo-4-(hepta-

pyridine-3-yl

fluoro-n-propylsul-

finyl)phenyl

1694
pyrazine-2-yl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1695
furan-2-yl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1696
thiophene-2-yl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsul-

finyl)phenyl

1697
phenyl
Me
Me
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1698
2-methylphenyl
Me
Me
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1699
4-methylphenyl
Me
Me
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1700
2-fluorophenyl
Me
Me
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1701
3-fluorophenyl
Me
Me
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1702
4-fluorophenyl
Me
Me
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1703
2-chlorophenyl
Me
Me
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1704
4-chlorophenyl
Me
Me
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1705
2-bromophenyl
Me
Me
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1706
2-iodophenyl
Me
Me
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1707
3-cyanophenyl
Me
Me
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1708
4-cyanophenyl
Me
Me
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1709
2-nitrophenyl
Me
Me
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1710
3-nitrophenyl
Me
Me
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1711
4-nitrophenyl
Me
Me
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1712
2-trifluoro-
Me
Me
F
H
2,6-dimethyl-4-(hepta-

methylphenyl

fluoroisopropyl)phenyl

1713
4-trifluoro-
Me
Me
F
H
2,6-dimethyl-4-(hepta-

methylphenyl

fluoroisopropyl)phenyl

1714
4-trifluoro-
Me
Me
F
H
2,6-dimethyl-4-(hepta-

methoxyphenyl

fluoroisopropyl)phenyl

1715
2,3-difluoro-
Me
Me
F
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1716
2,4-difluoro-
Me
Me
F
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1717
2,5-difluoro-
Me
Me
F
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1718
2,6-difluoro-
Me
Me
F
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1719
2,4-dichloro-
Me
Me
F
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1720
2,6-dichloro-
Me
Me
F
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1721
3,4-dichloro-
Me
Me
F
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1722
2-chloro-4-
Me
Me
F
H
2,6-dimethyl-4-(hepta-

nitrophenyl

fluoroisopropyl)phenyl

1723
2-chloro-4-
Me
Me
F
H
2,6-dimethyl-4-(hepta-

fluorophenyl

fluoroisopropyl)phenyl

1724
2-chloro-6-
Me
Me
F
H
2,6-dimethyl-4-(hepta-

fluorophenyl

fluoroisopropyl)phenyl

1725
4-chloro-2-
Me
Me
F
H
2,6-dimethyl-4-(hepta-

fluorophenyl

fluoroisopropyl)phenyl

1726
4-chloro-2-
Me
Me
F
H
2,6-dimethyl-4-(hepta-

nitrophenyl

fluoroisopropyl)phenyl

1727
2,3,6-trifluoro
Me
Me
F
H
2,6-dimethyl-4-(hepta-

phenyl

fluoroisopropyl)phenyl

1728
pyridine-2-yl
Me
Me
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1729
pyridine-3-yl
Me
Me
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1730
2-fluoropyr-
Me
Me
F
H
2,6-dimethyl-4-(hepta-

idine-3-yl

fluoroisopropyl)phenyl

1731
2-chloropyr-
Me
Me
F
H
2,6-dimethyl-4-(hepta-

idine-3-yl

fluoroisopropyl)phenyl

1732
2-chloropyr-
Me
Me
F
H
2,6-dimethyl-4-(hepta-

idine-5-yl

fluoroisopropyl)phenyl

1733
2-methylthio
Me
Me
F
H
2,6-dimethyl-4-(hepta-

pyridine-3-yl

fluoroisopropyl)phenyl

1734
pyrazine-2-yl
Me
Me
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1735
furan-2-yl
Me
Me
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1736
thiophene-2-yl
Me
Me
F
H
2,6-dimethyl-4-(hepta-

fluoroisopropyl)phenyl

1737
phenyl
Me
Me
F
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1738
2-methylphenyl
Me
Me
F
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1739
4-methylphenyl
Me
Me
F
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1740
2-fluorophenyl
Me
Me
F
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1741
3-fluorophenyl
Me
Me
F
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1742
4-fluorophenyl
Me
Me
F
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1743
2-chlorophenyl
Me
Me
F
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1744
4-chlorophenyl
Me
Me
F
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1745
2-bromophenyl
Me
Me
F
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1746
2-iodophenyl
Me
Me
F
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1747
3-cyanophenyl
Me
Me
F
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1748
4-cyanophenyl
Me
Me
F
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1749
2-nitrophenyl
Me
Me
F
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1750
3-nitrophenyl
Me
Me
F
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1751
4-nitrophenyl
Me
Me
F
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1752
2-trifluoro-
Me
Me
F
H
2-bromo-4-(hepta-

methylphenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1753
4-trifluoro-
Me
Me
F
H
2-bromo-4-(hepta-

methylphenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1754
4-trifluoro-
Me
Me
F
H
2-bromo-4-(hepta-

methoxyphenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1755
2,3-difluoro-
Me
Me
F
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1756
2,4-difluoro-
Me
Me
F
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1757
2,5-difluoro-
Me
Me
F
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1758
2,6-difluoro-
Me
Me
F
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1759
2,4-dichloro-
Me
Me
F
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1760
2,6-dichloro-
Me
Me
F
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1761
3,4-dichloro-
Me
Me
F
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1762
2-chloro-4-
Me
Me
F
H
2-bromo-4-(hepta-

nitrophenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1763
2-chloro-4-
Me
Me
F
H
2-bromo-4-(hepta-

fluorophenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1764
2-chloro-6-
Me
Me
F
H
2-bromo-4-(hepta-

fluorophenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1765
4-chloro-2-
Me
Me
F
H
2-bromo-4-(hepta-

fluorophenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1766
4-chloro-2-
Me
Me
F
H
2-bromo-4-(hepta-

nitrophenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1767
2,3,6-trifluoro
Me
Me
F
H
2-bromo-4-(hepta-

phenyl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1768
pyridine-2-yl
Me
Me
F
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1769
pyridine-3-yl
Me
Me
F
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1770
2-fluoropyr-
Me
Me
F
H
2-bromo-4-(hepta-

idine-3-yl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1771
2-chloropyr-
Me
Me
F
H
2-bromo-4-(hepta-

idine-3-yl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1772
2-chloropyr-
Me
Me
F
H
2-bromo-4-(hepta-

idine-5-yl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1773
2-methylthio
Me
Me
F
H
2-bromo-4-(hepta-

pyridine-3-yl

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1774
pyrazine-2-yl
Me
Me
F
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1775
furan-2-yl
Me
Me
F
H
2-bromo-4-(hepta-

fluoroisopropyl)-6-

(methylsulfonyl)phenyl

1776
thiophene-2-yl
Me
Me
F
H
2-bromo-4-(hepta-

fluoroisopropyl)-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-trifluoro-
Me
Me
F
H
2-n-propyl-6-iodo-4-

methylphenyl

(heptafluoroisopropyl)

phenyl

1793
4-trifluoro-
Me
Me
F
H
2-n-propyl-6-iodo-4-

methylphenyl

(heptafluoroisopropyl)

phenyl

1794
4-trifluoro-
Me
Me
F
H
2-n-propyl-6-iodo-4-

methoxyphenyl

(heptafluoroisopropyl)

phenyl

1795
2,3-difluoro-
Me
Me
F
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1796
2,4-difluoro-
Me
Me
F
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1797
2,5-difluoro-
Me
Me
F
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1798
2,6-difluoro-
Me
Me
F
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1799
2,4-dichloro-
Me
Me
F
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1800
2,6-dichloro-
Me
Me
F
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1801
3,4-dichloro-
Me
Me
F
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1802
2-chloro-4-
Me
Me
F
H
2-n-propyl-6-iodo-4-

nitrophenyl

(heptafluoroisopropyl)

phenyl

1803
2-chloro-4-
Me
Me
F
H
2-n-propyl-6-iodo-4-

fluorophenyl

(heptafluoroisopropyl)

phenyl

1804
2-chloro-6-
Me
Me
F
H
2-n-propyl-6-iodo-4-

fluorophenyl

(heptafluoroisopropyl)

phenyl

1805
4-chloro-2-
Me
Me
F
H
2-n-propyl-6-iodo-4-

fluorophenyl

(heptafluoroisopropyl)

phenyl

1806
4-chloro-2-
Me
Me
F
H
2-n-propyl-6-iodo-4-

nitrophenyl

(heptafluoroisopropyl)

phenyl

1807
2,3,6-trifluoro
Me
Me
F
H
2-n-propyl-6-iodo-4-

phenyl

(heptafluoroisopropyl)

phenyl

1808
pyridine-2-yl
Me
Me
F
H
2-n-propyl-6-iodo-4-

(heptafluoroisopropyl)

phenyl

1809
pyridine-3-yl
Me
Me
F
H
2-n-propyl-6-iodo-4-

(heptafluoroisopropyl)

phenyl

1810
2-fluoropyr-
Me
Me
F
H
2-n-propyl-6-iodo-4-

idine-3-yl

(heptafluoroisopropyl)

phenyl

1811
2-chloropyr-
Me
Me
F
H
2-n-propyl-6-iodo-4-

idine-3-yl

(heptafluoroisopropyl)

phenyl

1812
2-chloropyr-
Me
Me
F
H
2-n-propyl-6-iodo-4-

idine-5-yl

(heptafluoroisopropyl)

phenyl

1813
2-methylthio
Me
Me
F
H
2-n-propyl-6-iodo-4-

pyridine-3-yl

(heptafluoroisopropyl)

phenyl

1814
pyrazine-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
thiophene-2-yl
Me
Me
F
H
2-n-propyl-6-iodo-4-

(heptafluoroisopropyl)

phenyl

1817
phenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1818
2-methylphenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1819
4-methylphenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1820
2-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1821
3-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1822
4-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1823
2-chlorophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1824
4-chlorophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1825
2-bromophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1826
2-iodophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1827
3-cyanophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1828
4-cyanophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1829
2-nitrophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1830
3-nitrophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1831
4-nitrophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1832
2-trifluoro-
Me
Me
F
H
2,6-dibromo-4-(hepta-

methylphenyl

fluoro-n-propylthio)

phenyl

1833
4-trifluoro-
Me
Me
F
H
2,6-dibromo-4-(hepta-

methylphenyl

fluoro-n-propylthio)

phenyl

1834
4-trifluoro-
Me
Me
F
H
2,6-dibromo-4-(hepta-

methoxyphenyl

fluoro-n-propylthio)

phenyl

1835
2,3-difluoro-
Me
Me
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1836
2,4-difluoro-
Me
Me
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1837
2,5-difluoro-
Me
Me
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1838
2,6-difluoro-
Me
Me
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1839
2,4-dichloro-
Me
Me
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1840
2,6-dichloro-
Me
Me
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1841
3,4-dichloro-
Me
Me
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1842
2-chloro-4-
Me
Me
F
H
2,6-dibromo-4-(hepta-

nitrophenyl

fluoro-n-propylthio)

phenyl

1843
2-chloro-4-
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluorophenyl

fluoro-n-propylthio)

phenyl

1844
2-chloro-6-
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluorophenyl

fluoro-n-propylthio)

phenyl

1845
4-chloro-2-
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluorophenyl

fluoro-n-propylthio)

phenyl

1846
4-chloro-2-
Me
Me
F
H
2,6-dibromo-4-(hepta-

nitrophenyl

fluoro-n-propylthio)

phenyl

1847
2,3,6-trifluoro
Me
Me
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1848
pyridine-2-yl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1849
pyridine-3-yl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1850
2-fluoropyr-
Me
Me
F
H
2,6-dibromo-4-(hepta-

idine-3-yl

fluoro-n-propylthio)

phenyl

1851
2-chloropyr-
Me
Me
F
H
2,6-dibromo-4-(hepta-

idine-3-yl

fluoro-n-propylthio)

phenyl

1852
2-chloropyr-
Me
Me
F
H
2,6-dibromo-4-(hepta-

idine-5-yl

fluoro-n-propylthio)

phenyl

1853
2-methylthio
Me
Me
F
H
2,6-dibromo-4-(hepta-

pyridine-3-yl

fluoro-n-propylthio)

phenyl

1854
pyrazine-2-yl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1855
furan-2-yl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1856
thiophene-2-yl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1857
phenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1858
2-methylphenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1859
4-methylphenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1860
2-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1861
3-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1862
4-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1863
2-chlorophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1864
4-chlorophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1865
2-bromophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1866
2-iodophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1867
3-cyanophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1868
4-cyanophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1869
2-nitrophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1870
3-nitrophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1871
4-nitrophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1872
2-trifluoro-
Me
Me
F
H
2,6-dibromo-4-(hepta-

methylphenyl

fluoro-n-propylthio)

phenyl

1873
4-trifluoro-
Me
Me
F
H
2,6-dibromo-4-(hepta-

methylphenyl

fluoro-n-propylthio)

phenyl

1874
4-trifluoro-
Me
Me
F
H
2,6-dibromo-4-(hepta-

methoxyphenyl

fluoro-n-propylthio)

phenyl

1875
2,3-difluoro-
Me
Me
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1876
2,4-difluoro-
Me
Me
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1877
2,5-difluoro-
Me
Me
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1878
2,6-difluoro-
Me
Me
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1879
2,4-dichloro-
Me
Me
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1880
2,6-dichloro-
Me
Me
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1881
3,4-dichloro-
Me
Me
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1882
2-chloro-4-
Me
Me
F
H
2,6-dibromo-4-(hepta-

nitrophenyl

fluoro-n-propylthio)

phenyl

1883
2-chloro-4-
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluorophenyl

fluoro-n-propylthio)

phenyl

1884
2-chloro-6-
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluorophenyl

fluoro-n-propylthio)

phenyl

1885
4-chloro-2-
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluorophenyl

fluoro-n-propylthio)

phenyl

1886
4-chloro-2-
Me
Me
F
H
2,6-dibromo-4-(hepta-

nitrophenyl

fluoro-n-propylthio)

phenyl

1887
2,3,6-trifluoro
Me
Me
F
H
2,6-dibromo-4-(hepta-

phenyl

fluoro-n-propylthio)

phenyl

1888
pyridine-2-yl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1889
pyridine-3-yl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1890
2-fluoropyr-
Me
Me
F
H
2,6-dibromo-4-(hepta-

idine-3-yl

fluoro-n-propylthio)

phenyl

1891
2-chloropyr-
Me
Me
F
H
2,6-dibromo-4-(hepta-

idine-3-yl

fluoro-n-propylthio)

phenyl

1892
2-chloropyr-
Me
Me
F
H
2,6-dibromo-4-(hepta-

idine-5-yl

fluoro-n-propylthio)

phenyl

1893
2-methylthio
Me
Me
F
H
2,6-dibromo-4-(hepta-

pyridine-3-yl

fluoro-n-propylthio)

phenyl

1894
pyrazine-2-yl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1895
furan-2-yl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1896
thiophene-2-yl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylthio)

phenyl

1897
2-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(penta-

fluoroethyl)phenyl

1898
2-fluorophenyl
Me
H
H
H
2-bromo-4-(heptafluoro

isopropyl)-6-methyl-

phenyl

1899
2-fluorophenyl
Me
H
H
H
2-ethyl-4-(heptafluoro

isopropyl)-6-methyl-

phenyl

1900
2-fluorophenyl
Me
H
H
H
4-(heptafluoroisopro-

pyl)-2-iodo-6-methyl-

phenyl

1901
2-fluorophenyl
Me
H
H
H
2-chloro-6-ethyl-4-

(heptafluoroisopro-

pyl)phenyl

1902
2-fluorophenyl
Me
H
H
H
2-bromo-6-ethyl-4-

(heptafluoroisopro-

pyl)phenyl

1903
2-fluorophenyl
Me
H
H
H
2-ethyl-4-(heptafluoro

isopropyl)-6-iodophenyl

1904
2-fluorophenyl
Me
H
H
H
4-(heptafluoroisopro-

pyl)-2-isopropyl-6-

methylphenyl

1905
2-fluorophenyl
Me
H
H
H
2-bromo-4-(heptafluoro-

isopropyl)-6-n-propyl-

phenyl

1906
2-fluorophenyl
Me
H
H
H
2-bromo-4-(heptafluoro-

isopropyl)-6-(trifluoro-

methylthio)phenyl

1907
2-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(trifluoro-

methylthio)phenyl

1908
2-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(penta-

fluoroethylthio)phenyl

1909
2-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(nona-

fluoro-n-butylthio)phenyl

1910
2-fluorophenyl
Me
H
H
H
2,6-dichloro-4-(hepta-

fluoroisopropylsulfonyl)

phenyl

1911
2-fluorophenyl
Me
H
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsulfonyl)

phenyl

1912
2-fluorophenyl
Me
H
H
H
2-bromo-6-(heptafluoro-

isopropyloxy)-4-methyl-

pyridine-3-yl

1913
2-fluorophenyl
Me
H
H
H
2,4-dimethyl-6-(2,2,2-

trifluoro-1-trifluoro-

methylethoxy)pyridine-

3-yl

1914
2-fluorophenyl
Me
H
H
H
2-chloro-4-methyl-6-

(2,2,2-trifluoro-1-tri-

fluoromethylethoxy)pyr-

idine-3-yl

1915
2-fluorophenyl
Me
H
H
H
2-bromo-4-methyl-6-

(2,2,2-trifluoro-1-tri-

fluoromethylethoxy)

pyridine-3-yl

1916
2-fluorophenyl
Me
H
H
H
2-iodo-4-methyl-6-

(2,2,2-trifluoro-1-tri-

fluoromethylethoxy)pyr-

idine-3-yl

1917
2-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(penta-

fluoroethyl)phenyl

1918
2-fluorophenyl
Me
H
F
H
2-bromo-4-(heptafluoro-

isopropyl)-6-methyl-

phenyl

1919
2-fluorophenyl
Me
H
F
H
2-ethyl-4-(heptafluoro-

isopropyl)-6-methyl-

phenyl

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-(heptafluoro

isopropyl)-6-iodophenyl

1924
2-fluorophenyl
Me
H
F
H
4-(heptafluoroisopropyl)-

2-isopropyl-6-methyl-

phenyl

1925
2-fluorophenyl
Me
H
F
H
2-bromo-4-(heptafluoro-

isopropyl)-6-n-propyl-

phenyl

1926
2-fluorophenyl
Me
H
F
H
2-bromo-4-(heptafluoro-

isopropyl)-6-(trifluoro-

methylthio)phenyl

1927
2-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(trifluoro-

methylthio)phenyl

1928
2-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(penta-

fluoroethylthio)phenyl

1929
2-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(nona-

fluoro-n-butylthio)phenyl

1930
2-fluorophenyl
Me
H
F
H
2,6-dichloro-4-(hepta-

fluoroisopropylsulfonyl)

phenyl

1931
2-fluorophenyl
Me
H
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsulfonyl)

phenyl

1932
2-fluorophenyl
Me
H
F
H
2-bromo-6-(heptafluoro-

isopropyloxy)-4-methyl-

pyridine-3-yl

1933
2-fluorophenyl
Me
H
F
H
2,4-dimethyl-6-(2,2,2-

trifluoro-1-trifluoro-

methylethoxy)pyridine-

3-yl

1934
2-fluorophenyl
Me
H
F
H
2-chloro-4-methyl-6-

(2,2,2-trifluoro-1-tri-

fluoromethylethoxy)

pyridine-3-yl

1935
2-fluorophenyl
Me
H
F
H
2-bromo-4-methyl-6-

(2,2,2-trifluoro-1-tri-

fluoromethylethoxy)

pyridine-3-yl

1936
2-fluorophenyl
Me
H
F
H
2-iodo-4-methyl-6-

(2,2,2-trifluoro-1-tri-

fluoromethylethoxy)

pyridine-3-yl

1937
2-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(penta-

fluoroethyl)phenyl

1938
2-fluorophenyl
Me
Me
H
H
2-bromo-4-(heptafluoro-

isopropyl)-6-methyl-

phenyl

1939
2-fluorophenyl
Me
Me
H
H
2-ethyl-4-(heptafluoro-

isopropyl)-6-methyl-

phenyl

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-(heptafluoro

isopropyl)-6-iodophenyl

1944
2-fluorophenyl
Me
Me
H
H
4-(heptafluoroisopropyl)-

2-isopropyl-6-methyl-

phenyl

1945
2-fluorophenyl
Me
Me
H
H
2-bromo-4-(heptafluoro-

isopropyl)-6-n-propyl-

phenyl

1946
2-fluorophenyl
Me
Me
H
H
2-bromo-4-(heptafluoro-

isopropyl)-6-(trifluoro-

methylthio)phenyl

1947
2-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(trifluoro

methylthio)phenyl

1948
2-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(penta-

fluoroethylthio)phenyl

1949
2-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(nona-

fluoro-n-butylthio)

phenyl

1950
2-fluorophenyl
Me
Me
H
H
2,6-dichloro-4-(hepta-

fluoroisopropylsulfonyl)

phenyl

1951
2-fluorophenyl
Me
Me
H
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsulfonyl)

phenyl

1952
2-fluorophenyl
Me
Me
H
H
2-bromo-6-(heptafluoro-

isopropyloxy)-4-methyl-

pyridine-3-yl

1953
2-fluorophenyl
Me
Me
H
H
2,4-dimethyl-6-(2,2,2-tri-

fluoro-1-trifluoromethyl-

ethoxy)pyridine-3-yl

1954
2-fluorophenyl
Me
Me
H
H
2-chloro-4-methyl-6-

(2,2,2-trifluoro-1-tri-

fluoromethylethoxy)

pyridine-3-yl

1955
2-fluorophenyl
Me
Me
H
H
2-bromo-4-methyl-6-

(2,2,2-trifluoro-1-tri-

fluoromethylethoxy)

pyridine-3-yl

1956
2-fluorophenyl
Me
Me
H
H
2-iodo-4-methyl-6-

(2,2,2-trifluoro-1-tri-

fluoromethylethoxy)

pyridine-3-yl

1957
2-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(penta-

fluoroethyl)phenyl

1958
2-fluorophenyl
Me
Me
F
H
2-bromo-4-(heptafluoro-

isopropyl)-6-methyl-

phenyl

1959
2-fluorophenyl
Me
Me
F
H
2-ethyl-4-(heptafluoro-

isopropyl)-6-methyl

phenyl

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-(heptafluoro

isopropy)-6-iodophenyl

1964
2-fluorophenyl
Me
Me
F
H
4-(heptafluoroisopropyl)-

2-isopropyl-6-methyl

phenyl

1965
2-fluorophenyl
Me
Me
F
H
2-bromo-4-(heptafluoro-

isopropyl)-6-n-propyl-

phenyl

1966
2-fluorophenyl
Me
Me
F
H
2-bromo-4-(heptafluoro-

isopropyl)-6(trifluoro-

methylthio)phenyl

1967
2-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(trifluoro

methylthio)phenyl

1968
2-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(penta-

fluoroethylthio)phenyl

1969
2-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(nona-

fluoro-n-butylthio)

phenyl

1970
2-fluorophenyl
Me
Me
F
H
2,6-dichloro-4-(hepta-

fluoroisopropylsulfonyl)

phenyl

1971
2-fluorophenyl
Me
Me
F
H
2,6-dibromo-4-(hepta-

fluoro-n-propylsulfonyl)

phenyl

1972
2-fluorophenyl
Me
Me
F
H
2-bromo-6-(heptafluoro-

isopropyloxy)-4-methyl-

pyridine-3-yl

1973
2-fluorophenyl
Me
Me
F
H
2,4-dimethyl-6-(2,2,2-

trifluoro-1-trifluoro-

methylethoxy)pyridine-

3-yl

1974
2-fluorophenyl
Me
Me
F
H
2-chloro-4-methyl-6-

(2,2,2-trifluoro-1-tri-

fluoromethylethoxy)pyr-

idine-3-yl

1975
2-fluorophenyl
Me
Me
F
H
2-bromo-4-methyl-6-

(2,2,2-trifluoro-1-tri-

fluoromethylethoxy)

pyridine-3-yl

1976
2-fluorophenyl
Me
Me
F
H
2-iodo-4-methyl-6-

(2,2,2-trifluoro-1-tri-

fluoromethylethoxy)

pyridine-3-yl

(A₃, A₄=carbon atoms; X, R₂=hydrogen atoms; G₁, G₂=oxygen atoms; n=0)

TABLE 4

Compound

Nos.
Q₁
R₁
A₁
A₂
Q₂

2001
phenyl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2002
2-methylphenyl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2003
4-methylphenyl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2004
2-fluorophenyl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2005
3-fluorophenyl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2006
4-fluorophenyl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2007
2-chlorophenyl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2008
4-chlorophenyl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2009
2-bromophenyl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2010
2-iodophenyl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2011
3-cyanophenyl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2012
4-cyanophenyl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2013
2-nitrophenyl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2014
3-nitrophenyl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2015
4-nitrophenyl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2016
2-trifluoromethyl
H
N
C
2,6-dimethyl-4-heptafluoro

phenyl

isopropylphenyl

2017
4-trifluoromethyl
H
N
C
2,6-dimethyl-4-heptafluoro

phenyl

isopropylphenyl

2018
4-trifluoromethoxy
H
N
C
2,6-dimethyl-4-heptafluoro

phenyl

isopropylphenyl

2019
2,3-difluorophenyl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2020
2,4-difluorophenyl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2021
2,5-difluorophenyl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2022
2,6-difluorophenyl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2023
2,4-dichlorophenyl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2024
2,6-dichlorophenyl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2025
3,4-dichlorophenyl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2026
2-chloro-4-nitro
H
N
C
2,6-dimethyl-4-heptafluoro

phenyl

isopropylphenyl

2027
2-chloro-4-fluoro
H
N
C
2,6-dimethyl-4-heptafluoro

phenyl

isopropylphenyl

2028
2-chloro-6-fluoro
H
N
C
2,6-dimethyl-4-heptafluoro

phenyl

isopropylphenyl

2029
4-chloro-2-fluoro
H
N
C
2,6-dimethyl-4-heptafluoro

phenyl

isopropylphenyl

2030
4-chloro-2-nitro
H
N
C
2,6-dimethyl-4-heptafluoro

phenyl

isopropylphenyl

2031
2,3,6-trifluoro
H
N
C
2,6-dimethyl-4-heptafluoro

phenyl

isopropylphenyl

2032
pyridine-2-yl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2033
pyridine-3-yl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2034
pyridine-4-yl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2035
2-fluoropyridine-
H
N
C
2,6-dimethyl-4-heptafluoro

3-yl

isopropylphenyl

2036
2-chloropyridine-
H
N
C
2,6-dimethyl-4-heptafluoro

3-yl

isopropylphenyl

2037
2-chloropyridine-
H
N
C
2,6-dimethyl-4-heptafluoro

5-yl

isopropylphenyl

2038
2-methylthio
H
N
C
2,6-dimethyl-4-heptafluoro

pyridine-3-yl

isopropylphenyl

2039
pyrazine-2-yl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2040
furan-2-yl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2041
thiophene-2-yl
H
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

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-

propylthio)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-(heptafluoro-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-

phenyl

propylthio)phenyl

2058
4-trifluoromethyl
H
N
C
2,6-dibromo-4-(heptafluoro-n-

phenyl

propylthio)phenyl

2059
4-trifluoromethoxy
H
N
C
2,6-dibromo-4-(heptafluoro-n-

phenyl

propylthio)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-

phenyl

propylthio)phenyl

2068
2-chloro-4-fluoro
H
N
C
2,6-dibromo-4-(heptafluoro-n-

phenyl

propylthio)phenyl

2069
2-chloro- 6-fluoro
H
N
C
2,6-dibromo-4-(heptafluoro-n-

phenyl

propylthio)phenyl

2070
4-chloro-2-fluoro
H
N
C
2,6-dibromo-4-(heptafluoro-n-

phenyl

propylthio)phenyl

2071
4-chloro-2-nitro
H
N
C
2,6-dibromo-4-(heptafluoro-n-

phenyl

propylthio)phenyl

2072
2,3,6-trifluoro
H
N
C
2,6-dibromo-4-(heptafluoro-n-

phenyl

propylthio)phenyl

2073
pyridine-2-yl
H
N
C
2,6-dibromo-4-(heptafluoro-n-

propylthio)phenyl

2074
pyridine-3-yl
H
N
C
2,6-dibromo-4-(heptafluoro-n-

propylthio)phenyl

2075
2-fluoropyridine-
H
N
C
2,6-dibromo-4-(heptafluoro-n-

3-yl

propylthio)phenyl

2076
2-chloropyridine-
H
N
C
2,6-dibromo-4-(heptafluoro-n-

3-yl

propylthio)phenyl

2077
2-chloropyridine-
H
N
C
2,6-dibromo-4-(heptafluoro-n-

5-yl

propylthio)phenyl

2078
2-methylthio
H
N
C
2,6-dibromo-4-(heptafluoro-n-

pyridine-3-yl

propylthio)phenyl

2079
pyrazine-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
thiophene-2-yl
H
N
C
2,6-dibromo-4-(heptafluoro-n-

propylthio)phenyl

2082
phenyl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2083
2-methylphenyl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2084
4-methylphenyl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2085
2-fluorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2086
3-fluorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2087
4-fluorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2088
2-chlorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2089
4-chlorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2090
2-bromophenyl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2091
2-iodophenyl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2092
3-cyanophenyl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2093
4-cyanophenyl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2094
2-nitrophenyl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2095
3-nitrophenyl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2096
4-nitrophenyl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2097
2-trifluoromethyl
Me
N
C
2,6-dimethyl-4-heptafluoro

phenyl

isopropylphenyl

2098
4-trifluoromethyl
Me
N
C
2,6-dimethyl-4-heptafluoro

phenyl

isopropylphenyl

2099
4-trifluoromethoxy
Me
N
C
2,6-dimethyl-4-heptafluoro

phenyl

isopropylphenyl

2100
2,3-difluorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2101
2,4-difluorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2102
2,5-difluorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2103
2,6-difluorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2104
2,4-dichlorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2105
2,6-dichlorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2106
3,4-dichlorophenyl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2107
2-chloro-4-nitro
Me
N
C
2,6-dimethyl-4-heptafluoro

phenyl

isopropylphenyl

2108
2-chloro-4-fluoro
Me
N
C
2,6-dimethyl-4-heptafluoro

phenyl

isopropylphenyl

2109
2-chloro-6-fluoro
Me
N
C
2,6-dimethyl-4-heptafluoro

phenyl

isopropylphenyl

2110
4-chloro-2-fluoro
Me
N
C
2,6-dimethyl-4-heptafluoro

phenyl

isopropylphenyl

2111
4-chloro-2-nitro
Me
N
C
2,6-dimethyl-4-heptafluoro

phenyl

isopropylphenyl

2112
2,3,6-trifluoro
Me
N
C
2,6-dimethyl-4-heptafluoro

phenyl

isopropylphenyl

2113
pyridine-2-yl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2114
pyridine-3-yl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2115
2-fluoropyridine-
Me
N
C
2,6-dimethyl-4-heptafluoro

3-yl

isopropylphenyl

2116
2-chloropyridine-
Me
N
C
2,6-dimethyl-4-heptafluoro

3-yl

isopropylphenyl

2117
2-chloropyridine-
Me
N
C
2,6-dimethyl-4-heptafluoro

5-yl

isopropylphenyl

2118
2-methylthio
Me
N
C
2,6-dimethyl-4-heptafluoro

pyridine-3-yl

isopropylphenyl

2119
pyrazine-2-yl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2120
furan-2-yl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2121
thiophene-2-yl
Me
N
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

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-

phenyl

propylthio)phenyl

2138
4-trifluoromethyl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-

phenyl

propylthio)phenyl

2139
4-trifluoromethoxy
Me
N
C
2,6-dibromo-4-(heptafluoro-n-

phenyl

propylthio)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-

propythio)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-

phenyl

propylthio)phenyl

2148
2-chloro-4-fluoro
Me
N
C
2,6-dibromo-4-(heptafluoro-n-

phenyl

propylthio)phenyl

2149
2-chloro-6-fluoro
Me
N
C
2,6-dibromo-4-(heptafluoro-n-

phenyl

propylthio)phenyl

2150
4-chloro-2-fluoro
Me
N
C
2,6-dibromo-4-(heptafluoro-n-

phenyl

propylthio)phenyl

2151
4-chloro-2-nitro
Me
N
C
2,6-dibromo-4-(heptafluoro-n-

phenyl

propylthio)phenyl

2152
2,3,6-trifluoro
Me
N
C
2,6-dibromo-4-(heptafluoro-n-

phenyl

propylthio)phenyl

2153
pyridine-2-yl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-

propylthio)phenyl

2154
pyridine-3-yl
Me
N
C
2,6-dibromo-4-(heptafluoro-n-

propylthio)phenyl

2155
2-fluoropyridine-
Me
N
C
2,6-dibromo-4-(heptafluoro-n-

3-yl

propylthio)phenyl

2156
2-chloropyridine-
Me
N
C
2,6-dibromo-4-(heptafluoro-n-

3-yl

propylthio)phenyl

2157
2-chloropyridine-
Me
N
C
2,6-dibromo-4-(heptafluoro-n-

5-yl

propylthio)phenyl

2158
2-methylthio
Me
N
C
2,6-dibromo-4-(heptafluoro-n-

pyridine-3-yl

propylthio)phenyl

2159
pyrazine-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
thiophene-2-yl
Me
N
C
2,6-dibromo-4-(heptafluoro-

n-propylthio)phenyl

2162
phenyl
H
C
N
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2163
phenyl
H
C
N-oxide
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2164
phenyl
H
N-oxide
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

2165
2-fluorophenyl
H
N-oxide
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

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-heptafluoro

isopropylphenyl

2169
2-fluorophenyl
Me
N-oxide
C
2,6-dimethyl-4-heptafluoro

isopropylphenyl

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

(R₁, R₂, X₁, X₂, X₃, X₄=hydrogen atoms; Q₁=phenyl)

TABLE 5

Com-

pound

Nos.
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-(methyl-

sulfonyl)phenyl

2211
S
O
2-bromo-4-(heptafluoroisopropyl)-6-(methyl-

sulfonyl)phenyl

2212
S
S
2-bromo-4-(heptafluoroisopropyl)-6-(methyl-

sulfonyl)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-dichloro-4-(heptafluoro-n-propylthio)phenyl

2221
S
S
2,6-dichloro-4-(heptafluoro-n-propylthio)phenyl

The physical properties of the compound represented by the general formula (1) of the present invention are shown in Table 6 below. Tetramethylsilane is used as an internal standard substance to record shift values of ¹H-NMR as shown herein, unless otherwise particularly mentioned.

TABLE 6

Compound

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,), 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-.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, 7.8Hz), 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 7.45-7.61(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)

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).

1244
(CDCl₃) δ 2.29(6H, s), 3.52(3H, s), 7.21-7.23(1H, m),

7.28-7.30(1H, m), 7.35(2H, m), 7.41(1H, m), 7.72(2H,

m), 8.01(1H, t, J = 6.8 Hz), 8.53(2H, 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).

Typical compounds of the compound represented by the general formula (2) that is an active ingredient of the insecticide of the present invention are illustrated in Table 7 below, but the present invention is not restricted thereto.

TABLE 7

Compound

No.
X₂
R₃
R₄
R₅
Q₃

3000
F
2,2,2-trifluoro
H
H
2,6-dimethyl-4-(hepta

ethyl

fluoroisopropyl)

phenyl

3001
H
1,3-difluoro
H
H
2,6-dimethyl-4-(hepta

2-propyl

fluoroisopropyl)

phenyl

3002
F
2-chloroethyl
H
H
2,6-dimethyl-4-(hepta

fluoroisopropyl)

phenyl

Typical compounds of the compound represented by the general formula (3) that is an active ingredient of the fungicide of the present invention are illustrated in Table 8 below, but the present invention is not restricted thereto.

Incidentally, in Table 8, Me refers to a methyl group, i-Pr refers to an isopropyl group, and t-Bu refers to a tertiary butyl group.

TABLE 8

Compound

No.
R11
R12
R13
R14
R15
R16
R17
R18

3003
i-Pr
H
i-Pr
H
H
H
H

3004
i-Pr
H
t-Bu
H
H
H
H

3005
i-Pr
H
i-Pr
H
H
H
H

Typical compounds of the compound represented by the general formula (4) that is an active ingredient of the fungicide of the present invention are illustrated in Table 9 below, but the present invention is not restricted thereto.

Incidentally, in Table 9, Me refers to a methyl group, i-Pr refers to an isopropyl group, and t-Bu refers to a tertiary butyl group.

TABLE 9

Compound

No.
R21
R22
R23
R24
R25
R26
R27
R28

3006
F3CCH2
H
i-Pr
H
H
H
H

3007
F3CCH2
H
t-Bu
H
H
H
H

3008
F3CCH2
H
i-Pr
H
H
H
H

The insecticidal and fungicidal composition of the present invention exhibits excellent insecticidal and fungicidal effects and exerts an accurate control effect on harmful diseases and insect pests. As such insect pests, there can be exemplified, for example, LEPIDOPTERA such as swift moth (Endoclyta excrescens), grape tree-borer (Endoclyta sinensis), swift moth (Palpifer sexnotata), strawberry tortrix moth (Acleris comariana), summer fruit tortrix moth (Adoxophyes orana fasciata), small tea tortrix moth (Adoxophyes sp.), Asiatic leaf roller (Archips breviplicanus), apple tortrix (Archips fuscocupreanus), brown oak tortrix (Archips xylosteanus), tortrix moth (Bactra furfurana), tobacco leaf worm (Cnephasia cinereipalpana), nut fruit tortrix (Cydia kurokoi), greenish chestnut moth (Eucoenogenes aestuosa), Manchurian fruit moth (Grapholita inopinata), oriental fruit moth (Grapholita molesta), oriental tea tortrix moth (Homona magnanima), leaf roller (Hoshinoa adumbratana), soybean pod borer (Leguminivora glycinivorella), adzuki bean pod worm (Matsumuraeses azukivora), soybean pod worm (Matsumuraeses falcana), soybean pod worm (Matsumuraeses phaseoli), mulberry leaf roller (Olethreutes mori), apple fruit licker (Spilonota lechriaspis), eye-spotted bud moth (Spilonota ocellana), European grape berry moth (Eupoecillia ambiguella), arrowhead moth (Phalonidia mesotypa), mugwort moth (Phtheochroides clandestine), codling moth (Cydia pomonella), grape berry moth (Endopiza viteana), mulberry bagworm (Bambalina sp.), giant bagworm (Eumeta japonica), tea bagworm (Eumeta minuscula), European grain moth (Nemapogon granellus), case making clothes moth (Tinea translucens), pear leaf miner (Bucculatrix pyrivorella), peach leaf miner (Lyonetia clerkella), apple leaf miner (Lyonetia prunifoliella), soybean leaf roller (Caloptilia soyella), tea leaf roller (Caloptilia theivora), apple leaf miner (Caloptilia zachrysa), persimmon leaf miner (Cuphodes diospyrosella), apple leaf miner (Phyllonorycter ringoniella), pear bark miner (Spulerina astaurota), citrus leaf miner (Phyllocnistis citrella), grape leaf miner (Phyllocnistis toparcha), allium leaf miner (Acrolepiopsis sapporensis), yam leaf miner (Acrolepiopsis suzukiella), diamondback moth (Plutella xylostella), apple fruit moth (Argyresthia conjugella), grape clearwing moth (Paranthrene regalis), cherry tree borer (Synanthedon hector), persimmon fruit moth (Stathmopoda masinissa), sweet potato leaf folder (Brachmia triannulella), pink bollworm (Pectinophora gossypiella), potato tuber moth (Phthorimaea operculella), peach fruit moth (Carposina niponensis), pear leaf worm (Illiberis pruni), Chinese cochlid (Latoia sinica), oriental moth (Monema flavescens), pear stinging caterpillar (Narosoideus flavidorsalis), green stinging caterpillar (Parasa consocia), persimmon cochlid (Scopelodes contracus), rice striped stem borer (Chilo suppressalis), rice leaffolder (Cnaphalocrocis medinalis), yellow peach moth (Conogethes punctiferalis), cucumber moth (Diaphania indica), pear fruit moth (Ectomyelois pyrivorella), tobacco moth (Ephestia elutella), Mediterranean flour moth (Ephestia kuehniella), limabean pod borer (Etiella zinckenella), persimmon bark borer (Euzophera batangensis), mulberry pyralid (Glyphodes pyloalis), cabbage webworm (Hellulla undalis), rice leaf roller (Marasmia exigua), legume pod borer (Maruca testulalis), cotton leaf roller (Notarcha derogate), Asian corn borer (Ostrinia furnacalis), adzuki bean borer (Ostrinia scapulalis), butterbur borer (Ostrinia zaguliaevi), bluegrass webworm moth (Parapediasia teterrella), peppered moth (Pleuroptya ruralis), Indian-meal moth (Plodia interpunctella), yellow stem borer (Scirpophaga incertulas), common straight swift butterfly (Parnara guttata), large swallowtail butterfly (Papilio helenus), papilionid butterfly (Papilio machaon hippocrates), citrus swallowtail butterfly (Papilio xuthus), Eastern pale clouded yellow (Colias erate poliographus), small white butterfly (Pieris rapae crucivora), long-tailed pea-blue (Lampides boeticus), orange moth (Angerona prunaria), Japanese giant looper (Ascotis selenaria), giant geometrid moth (Biston robustum), plum cankerworm (Cystidia couaggaria), pine moth (Dendrolimus spectabilis), tent moth (Malacosoma neustria testacea), apple caterpillar (Odonestis pruni japonensis), coffee hawk moth (Cephonodes hylas), hawk moth (Acosmeryx castanea), scarce chocolate-tip (Clostera anachoreta), poplar tip moth (Clostera anastomosis), black-marked prominent (Phalera flavescens), drab-brown moth (Phalerodonta manleyi), lobster moth (Stauropus fagi persimilis), tea tussock moth (Euproctis pseudoconspersa), brown tail moth (Euproctis similis), oriental tussock moth (Euproctis subflava), Asian gypsy moth (Lymantria dispar), white-spotted tussock moth (Orgyia thyellina) fall webworm moth (Hyphantria cunea), mulberry tiger moth (Spilosoma imparilis), three-spotted plusia (Acanthoplusia agnata), sweet potato leaf worm (Aedia leucomelas), black cutworm (Agrotis ipsilon), turnip moth (Agrotis segetum), cotton looper (Anomis flava), hibiscus leaf caterpillar (Anomis mesogona), beet semi-looper (Autographa nigrisigna), tiger moth (Trichoplusia ni), American boll worm (Helicoverpa armigera), oriental tobacco budworm (Helicoverpa assulta), flax budworm (Heliothis maritima), cabbage moth (Mamestra brassicae), green rice semilooper (Naranga aenescens), growth-blocking peptide (Pseudaletia separata), pink stem borer (Sesamia inferens), Japanese lawn grass cutworm (Spodoptera depravata), beet armyworm (Spodoptera exigua), oriental leafworm moth (Spodoptera litura), apple dagger moth (Triaena intermedia), sorrel cutworm (Viminia rumicis), spotted cutworm moth (Xestia c-nigrum) and the like;

Heteroptera of HEMIPTERA such as globular stink bug (Megacopta punctatissimum), black-shouldered shield bug (Carpocoris purpureipennis), sloe bug (Dolycoris baccarum), cabbage bug (Eurydema pulchrum), cabbage bug (Eurydema rugosum), 2-spotted sesame bug (Eysarcoris guttiger), white-spotted larger spined bug (Eysarcoris lewisi), white-spotted bug (Eysarcoris parvus), white-spotted stink bug (Eysarcoris ventralis), fruit-piercing stink bug (Glaucias subpunctatus), red-striped stink bug (Graphosoma rubrolineatum), brown marmorated stink bug (Halyomorpha mista), rice stink bug (Lagynotomus elongatus), eastern green stink bug (Nezara antennata), southern green stink bug (Nezara viridula), redbanded shield bug (Piezodorus hybneri), brownwinged green bug (Plautia stali), black rice bug (Scotinophara lurida), shield bug (Starioides iwasakii), winter cherry bug (Acanthocoris sordidus), Coreid bug (Anacanthocoris striicornis), narrow squash bug (Cletus punctiger), slender rice bug (Cletus trigonus), leaf-footed bug (Molipteryx fulginosa), paddy bug (Leptocorisa acuta), rice bug (Leptocorisa chinensis), rice bug (Leptocorisa oratorius), bean bug (Riptortus clavatus), carrot bug (Aeschynteles maculatus), plant bug (Liorhyssus hyalinus), oriental chinch bug (Cavelerius saccharivorus), chinch bug (Macropes obnubilus), ground bug (Pachybrachius luridus), lygaeid bug (Paromius exguus), seed bug (Togo hemipterus), red cotton bug (Dysdercus cingulatus), red bug (Dysdercus poecilus), chrysanthemum lace bug (Galeatus spinifrons), lace bug (Metasalis populi), silver magnolia lace bug (Stephanitis fasciicarina), pear lace bug (Stephanitis nashi), azalea lace bug (Stephanitis pyrioides), chestnut lace bug (Uhlerites debile), walnut lace bug (Uhlerites latius), alfalfa plant bug (Adelphocoris lineolatus), plant bug (Adelphocoris triannulatus), green leaf bug (Apolygus lucorum), pale green plant bug (Apolygus spinolai), sweet potato yellow bug (Creontiades pallidifer), tobacco leaf bug (Cyrtopeltis tennuis), plant bug (Ectometopterus micantulus), plant bug (Halticiellus insularis), apple leaf bug (Heterocordylus flavipes), mirid bug (Lygus disponsi), lygus bug (Lygus saundersi), mirid bug (Orthotylus flavosparsus), plant bug (Stenodema calcaratum), mired plant bug (Stenotus binotatus), sorghum plant bug (Stenotus rubrovittatus), broken back bug (Taylorilygus pallidulus), rice leaf bug (Trigonotylus coelestialium) and the like;

Homoptera such as large brown cicada (Graptopsaltria nigrofuscata), spittle bug (Aphrophora costalis), pine spittle bug (Aphrophora flavipes), grape spittle bug (Aphrophora vitis), spittle bug (Clovia punctata), meadow spittle bug (Philaenus spumarius), black-tipped leafhopper (Bothrogonia japonica), green leafhopper (Cicadella viridis), white leafhopper (Cofana spectra), oak leafhopper (Aguriahana quercus), polyphagous leafhopper (Alnetoidia alneti), citrus leafhopper (Apheliona ferruginea), grape leafhopper (Arboridia apicalis), small green leafhopper (Edwardsiana flavescens), rose leafhopper (Edwardsiana rosae), spruce leafhopper (Empoasca abietis), tea green leafhopper (Empoasca onukii), yellow rice leafhopper (Thaia subrufa), small citrus leafhopper (Zyginella citri), aster leafhopper (Macrosteles fascifrons), green rice leafhopper (Nephotettix cincticeps), green rice leafhopper (Nephotettix nigropictus), green leafhopper (Nephotettix virescens), apple leafhopper (Orientus ishidai), zigzag leafhopper (Recilia dorsalis), wheat leafhopper (Sorhoanus tritici), leafhopper (Speusotettix subfusculus), small brown plant hopper (Laodelphax striatellus), brown plant hopper (Nilaparvata lugens), planthopper (Numata muiri), maize plahthopper (Peregrinus maidis), sugarcane planthopper (Perkinsiella saccharicida), white backed planthopper (Sogatella furcifera), panicum planthopper (Sogatella panicicola), mulberry psyllid (Anomoneura mori), psyllid (Calophya nigridorsalis), Asian citrus psyllid (Diaphorina citri), psyllid (Mesohomotoma camphorae), abies sucker (Psylla abieti), jumping plant louse (Psylla alni), Japanese louse (Psylla jamatonica), apple psyllid (Psylla mali), black apple sucker (Psylla malivorella), larger pear sucker (Psylla pyrisuga), Tobira sucker (Psylla tobirae), camphor sucker (Trioza camphorae), sucker (Trioza quercicola), spiny whitefly (Aleurocanthus spiniferus), grape whitefly (Aleurolobus taonabae), sweet potato whitefly (Bemisia tabaci), citrus whitefly (Dialeurodes citri), greenhouse whitefly (Trialeurodes vaporariorum), silver leaf whitefly (Bemisia argentifolii), grape phylloxera (Viteus vitifolii), root aphid (Aphidounguis mali), woolly apple aphid (Eriosoma lanigerum), sugarcane root aphid (Geoica lucifuga), pea aphid (Acyrthosiphon pisum), spiraea aphid (Aphis citricola), cowpea aphid (Aphis craccivora), willow aphid (Aphis farinose yanagicola), cotton-melon aphid (Aphis gossypii), foxglove aphid (Aulacorthum solani), leafcurl plum aphid (Brachycaudus helichrysi), cabbage aphid (Brevicoryne brassicae), tulip bulb aphid (Dysaphis tulipae), European birch aphid (Euceraphis punctipennis), mealy plum aphid (Hyalopterus pruni), mustard aphid (Lipaphis erysimi), chrysanthemum aphid (Macrosiphoniella sanborni), potato aphid (Macrosiphum euphorbiae), bean aphid (Megoura crassicauda), pear aphid (Melanaphis siphonella), apple leaf-curling aphid (Myzus malisuctus), plum aphid (Myzus mumecola), green peach aphid (Myzus persicae), onion aphid (Neotoxoptera formosana), apple aphid (Ovatus malicolens), waterlily aphid (Rhopalosiphum nymphaeae), wheat aphid (Rhopalosiphum padi), rice root aphid (Rhopalosiphum rufiabdominalis), wormwood root aphid (Sappaphis piri), pear aphid (Schizaphis piricola), corn leaf aphid (Sitobion akebiae), rose aphid (Sitobion ibarae), black citrus aphid (Toxoptera aurantii), black citrus aphid (Toxoptera citricidus), peach aphid (Tuberocephalus momonis), Formosan lettuce aphid (Uroleucon formosanum), greenbug aphid (Schizaphis graminum), giant mealybug (Drosicha corpulenta), cottony cushion scale (Icerya purchasi), Matsumoto mealybug (Crisicoccus matsumotoi), pine mealybug (Crisicoccus pini), pear mealybug (Dysmicoccus wistariae), citrus mealybug (Planococcus citri), Japanese mealybug (Planococcus kraunhiae), citrus mealybug (Pseudococcus citriculus), comstock mealybug (Pseudococcus comstocki), Indian white wax scale (Ceroplastes ceriferus), pink wax scale (Ceroplastes rubens), soft scale (Coccus discrepans), brown soft scale (Coccus hesperidum), citricola scale (Coccus pseudomagnoliarum), Chinese white-wax scale (Ericerus pela), European fruit scale (Lecanium corni), European peach scale (Lecanium persicae), citrus cottony scale (Pulvinaria aurantii), cottony citrus scale (Pulvinaria citricola), cottony mulberry scale (Pulvinaria kuwacola), black scale (Saissetia oleae), citrus scale (Andaspis kashicola), California red scale (Aonidiella aurantii), citrus yellow scale (Aonidiella citrina), coconut scale (Aspidiotus destructor), oleander scale (Aspidiotus hederae), Florida red scale (Chrysomphalus ficus), San Jose scale (Comstockaspis perniciosa), dupla scale (Duplaspidiotus claviger), purple scale (Lepidosaphes beckii), oystershell scale (Lepidosaphes ulmi), pear scale (Lepholeucaspis japonica), pear scale (Parlatoreopsis pyri), armored scale (Parlatoria camelliae), tea black scale (Parlatoria theae), black parlatoria scale (Parlatoria ziziphi), fern scale (Pinnaspis aspidistrae), camphor scale (Pseudaonidia duplex) Japanese camellia scale (Pseudaonidia paeoniae), white peach scale (Pseudaulacaspis pentagona), white prunicola Scale (Pseudaulacaspis prunicola), arrowhead scale (Unaspis yanonensis) and the like;

COLEOPTERA such as brown chafer (Adoretus tenuimaculatus), cupreous chafer (Anomala cuprea), soybean beetle (Anomala rufocuprea), flower chafer (Eucetonia pilifera), flower beetle (Eucetonia roelofsi), yellowish elongate chafer (Heptophylla picea), cockchafer (Melolontha japonica), Japanese cockchafer (Mimela splendens), smaller green flower chafer (Oxycetonia jucunda), Japanese beetle (Popillia japonica), variegated carpet beetle (Anthrenus verbasci), black carpet beetle (Attagenus unicolor japonicus), cigarette beetle (Lasioderma serricorne), powder post beetle (Lyctus brunneus), corn sap beetle (Carpophilus dimidiatus), dried fruit beetle (Carpophilus hemipterus), herbivorous ladybird beetle (Epilachna vigintioctomaculata), spotted ladybird beetle (Epilachna vigintioctopunctata), Mexican bean beetle (Epilachna varivestis), black fungus beetle (Alphitobius laevigatus), beetle (Neatus picipes), flour beetle (Palorus ratzeburgii), depressed flour beetle (Palorus subdepressus), yellow mealworm beetle (Tenebrio molitor), rust red flour beetle (Tribolium castaneum), red flour beetle (Tribolium confusum), Japanese blister beetle (Epicauta gorhami), long-horn beetle (Aeolesthes chrysothrix), white-spotted longicorn beetle (Anoplophora malasiaca), Japanese pine sawyer beetle (Monochamus alternatus), yellow-spotted longicorn beetle (Psacothea hilaris) grape borer (Xylotrechus pyrrhoderus), monkeypod roundheaded borer (Xystrocera globosa), bean weevil (Acanthoscelides obtectus), Chinese bean weevil (Callosobruchus chinensis), southern cowpea weevil (Callosobruchus maculatus), cucurbit leaf beetle (Aulacophora femoralis), leaf beetle (Basilepta balyi), tortoise beetle (Cassida nebulosa), brown-blackish beetle (Chaetocnema concinna), chrysomelid leaf beetle (Colasposoma dauricum), asparagus leaf beetle (Criiceris quatuordecimpunctata), rice rootworm (Donacia provosti), alder chrysomelid beetle (Linaeidea aenea), leaf beetle (Luperomorpha tunebrosa), two-striped leaf beetle (Medythia nigrobilineata), rice leaf beetle (Oulema oryzae), tropical legume leaf beetle (Pagria signata), daikon leaf beetle (Phaedon brassicae), crucifer flea beetle (Phyllotreta striolata), Colorado potato beetle (Leptinotarsa decemlineata), corn root worm (Diabrotica sp.), weevil (Involvulus cupreus), peach curculio (Rhynchites heros), sweet potato weevil (Cylas formicarius), apple blossom weevil (Anthonomus pomorum), weevil (Ceuthorhynchidius albosuturalis), chestnut weevil (Curculio sikkimensis), rice-plant weevil (Echinocnemus squameus), West Indian sweet potato weevil (Euscepes postfasciatus), lesser clover leaf weevil (Hypera nigrirostris), Alfalfa weevil (Hypera postica), rice water weevil (Lissorhoptrus oryzophilus), Australian tomato weevil (Listroderes costirostris), common leaf weevil (Phyllobius armatus), Japanese weevil (Sitona japonicus), boll weevil (Anthonomus grandis), rice weevil (Sitophilus oryzae), maize weevil (Sitophilus zeamais), hunting billbug (Sphenophrus venatus vestitus), pine shoot beetle (Tomicus piniperda) and the like;

THYSANOPTERA such as grass thrips (Anaphothrips obscurus), cocksfoot thrips (Chirothrips manicatus), black tea thrips (Dendrothrips minowai), flower thrips (Frankliniella intonsa), thrips (Frankliniella lilivora), greenhouse thrips (Heliothrips haemorrhoidalis), composite thrips (Microcephalothrips abdominalis), oriental soybean thrips (Mycterothrips glycines), mulberry thrips (Pseudodendrothrips mori), yellow tea thrips (Scirtothrips dorsalis), redbanded thrips (Selenothrips rubrocinctus), oriental rice thrips (Stenchaetothrips biformis), thrips (Thrips alliorum), loquat thrips (Thrips coloratus), Eurasian yellow flower thrips (Thrips flavus), banana flower thrips (Thrips hawaiiensis), chrysanthemum thrips (Thrips nigropilosus), melon thrips (Thrips palmi), western flower thrips (Frankliniella occidentalis), light brown soybean thrips (Thrips setosus), gladiolus thrips (Thrips simplex), onion thrips (Thrips tabaci), rye thrips (Haplothrips aculeatus), Chinese thrips (Haplothrips chinensis), predatory thrips (Haplothrips kurdjumovi), red clover thrips (Haplothrips niger), thrips (Leeuwenia pasanii), camphor thrips (Liothrips floridensis), lily thrips (Liothrips vaneeckei), thrips (Litotetothrips pasaniae), Japanese gall-forming thrips (Ponticulothrips diospyrosi) and the like;

ORTHOPTERA such as American cockroach (Periplaneta americana) smokybrown cockroach (Periplaneta fuliginosa), Japanese cockroach (Periplaneta japonica), German cockroach (Blattella germanica), wild cockroach (Blattella lituricollis), Northern cone-headed long horn grasshopper (Homorocoryphus jezoensis), walker (Homorocoryphus lineosus), mole cricket (Gryllotalpa sp.), small rice grasshopper (Oxya hyla intricata), rice grasshopper (Oxya yezoensis), migratory locust (Locusta migratoria) and the like;

DIPTERA such as rice crane fly (Tipula aino), fungus gnat (Bradysia agrestis), soybean pod gall midge (Asphondylia sp.), melon fly (Dacus cucurbitae), oriental fruit fly (Dacus dorsalis), Japanese orange fly (Dacus tsuneonis), Japanese cherry fruit fly (Rhacochlaena japonica), rice leaf miner (Hydrellia griseola), rice whorl maggot (Hydrellia sasakii), fruit fly (Drosophila suzukii), rice stem maggot (Chlorops oryzae), wheat stem maggot (Meromyza nigriventris), rice leaf miner (Agromyza oryzae), garden pea leaf miner (Chromatomyia horticola), tomato leaf miner (Liriomyza bryoniae), stone leek leaf miner (Liriomyza chinensis), American serpentine leaf miner (Liriomyza trifolii), vegetable leaf miner (Liriomyza sativae), pea leaf miner (Liriomyza huidobrensis), onion maggot (Delia antiqua), onion maggot (Delia platura), beet leaf miner (Pegomya cunicularia), green bottle fly (Phormia regina), house fly (Musca domestica), mosquito (Culex pipiens pallens), malaria vector (Anopheles sinensis), Asian tiger mosquito (Aedes albopictus), mosquito (Culex pipiens molestus) and the like;

HYMENOPTERA such as cabbage sawfly (Athalia japonica), turnip sawfly (Athalia rosae ruficornis), apple argid sawfly (Arge mali) large rose sawfly (Arge pagana), oriental chestnut gall wasp (Dryocosmus kuriphilus), wood ant (Formica japonica) and the like;

ACARINA such as broad mite (Polyphagotarsonemus latus), cyclamen mite (Steneotarsonemus pallidus), fungus mite (Tarsonemus waitei), straw itch mite (Pyemotes ventricosus), blue oat mite (Penthaleus major), citrus flat mite (Brevipalpus lewisi), privet mite (Brevipalpus obovatus), pineapple flat mite (Dolichotetranychus floridanus), persimmon false spider mite (Tenuipalpus zhizhilashviliae), flat mite (Brevipalpus phoenicis), Tuckerellid mite (Tuckerella pavoniformis), clover mite (Bryobia praetiosa), brown almond mite (Bryobia rubrioculus), apricot spider mite (Eotetranychus boreus), spider mite (Eotetranychus geniculatus), spider mite (Eotetranychus pruni), 6-spotted mite (Eotetranychus sexmanaculatus), tetranychid mite (Eotetranychus smithi), red spider mite (Eotetranychus uncatus), sugi spider mite (Oligonychus hondoensis), southern red mite (Oligonychus ilicis), larch mite (Oligonychus karamatus), citrus red mite (Panonychus citri), European red mite (Panonychus ulmi), carmine spider mite (Tetranychus cinnabarinus), tea red spider mite (Tetranychus kanzawai), 2-spotted spider mite (Tetranychus urticae), hawthorn spider mite (Tetranychus viennensis), pink tea rust mite (Acaphylla theae), tulip bulb mite (Aceria tulipae), pink citrus rust mite (Aculops pelekassi), plum rust mite (Aculus fockeui), apple rust mite (Aculus schlechtendali), ribbed tea mite (Calacarus carinatus), grape leaf rust mite (Calepitrimerus vitis), pear rust mite (Epitrimerus pyri), Japanese pear rust mite (Eriophyes chibaensis), flour mite (Acarus siro), brown legged grain mite (Aleuroglyphus ovatus), bulb mite (Rhizoglyphus robini), mould mite (Tyrophagus putrescentiae), tropical rat mite (Ornithonyssus bacoti), scrub typhus mite (Leptotrombidium akamushi), moth (Leptotrombidium scutellaris), chigger mite (Leptotrombidium pallidum) and the like;

TYLENCHIDA such as bent grass nematode (Anguina agrostis) ear-cockle nematode (Anguina tritici), potato rot nematode (Ditylenchus destructor), tobacco stunt nematode (Tylenchorhynchus claytoni), sugar cane stylet nematode (Tylenchorhynchus martini), stunt nematode (Tylenchorhynchus sp.), rice root nematode (Hirschmanniella imamuri), rice root nematode (Hirschmanniella oryzae), coffee root-lesion nematode (Pratylenchus coffeae), lesion nematode (Pratylenchus convallariae), root lesion nematode (Pratylenchus fallax), root lesion nematode of tea (Pratylenchus loosi), California root lesion nematode (Pratylenchus neglectus), Cobb's root lesion nematode (Pratylenchus penetrans), plant root lesion nematode (Pratylenchus sp.), Steiner's spiral nematode (Helicotylenchus dihystera), grass spiral nematode (Helicotylenchus erythrinae), spiral nematode (Helicotylenchus sp.), lance nematode (Hoplolaimus sp.), reniform nematode (Rotylenchulus reniformis), British spiral nematode (Scutellonema brachyurum), oat nematode (Bidera avenae), cactus cyst nematode (Cactodera cacti), cyst nematode (Cryphodera sp.), gold-plated nematode (Globodera rostochiensis), Japanese cyst nematode (Heterodera elachista), soybean cyst nematode (Heterodera glycines), clover cyst nematode (Heterodera trifolii), peanut root-knot nematode (Meloidogyne arenaria), camellia root-knot nematode (Meloidogyne camelliae), root-knot nematode (Meloidogyne graminis), northern root-knot nematode (Meloidogyne hapla), southern root-knot nematode (Meloidogyne incognita), root-knot nematode (Meloidogyne sp.), citrus root nematode (Tylenchulus semipenetrans), fungivorous nematode (Aphelenchus avenae) and the like;

DORYLAIMIDA such as needle nematode (Longidorus martini), needle nematode (Longidorus sp.), American dagger nematode (Xiphinema americanum), dagger nematode (Xiphinema sp.), stubby root nematode (Trichodorus sp.) and the like;

THYSANURA such as oriental silverfish (Ctenolepisma villosa), silverfish (Lepisma saccharina), firebrat (Thermobia domestica) and the like;

ISOPTERA such as drywood termite (Cryptotermes domesticus), Formosan subterranean termite (Coptotermes formosanus), Japanese subterranean termite (Reticulitermes speratus), fungus-growing termite (Odontotermes formosanus) and the like;

PSOCOPTERA such as booklouse (Liposcelis bostrychophilus) and the like;

SIPHONAPTERA such as dog flea (Ctenocephalides canis) and the like;

ANOPLURA such as body louse (Pediculus humanus humanus) and the like;

CHILOPODA such as house centipede (Thereuronema tuberculata) and the like;

DIPLOPODA such as flat-backed millipede (Oxidus gracilis) and the like; and

MOLLUSCA such as terrestrial slug (Incilaria bilineata) and the like.

Furthermore, as such diseases, rice blast (Pyricularia oryzae) can be cited.

As the application methods of the insecticidal and fungicidal composition of the present invention, there can be exemplified, for example, application to the plant itself (foliar spraying), application to the nursery box (nursery box application), application to the soil (soil treatments such as soaking into soil, mixture into soil, side dressing, dispersion on soil or spraying on soil), application of paddy water (submerged application or rice field application), application to the seed (seed treatment) and the like.

The insecticidal and fungicidal composition of the present invention is generally prepared into conveniently usable forms according to an ordinary manner for preparation of agricultural and horticultural chemicals. That is, the composition may be blended with a suitable inert carrier, optically along with an adjuvant, in a proper proportion and prepared into a suitable preparation form such as a suspension, emulsifiable concentrate, soluble concentrate, wettable powder, granules, dust, tablets or the like through dissolution, separation, suspension, mixing, impregnation, adsorption or adhering.

The inert carrier which can be used in the present invention may be either solid or liquid. Such a material which can be an inert solid carrier includes, for example, soybean flour, cereal flour, wood flour, bark flour, saw dust, powdered tobacco stalks, powdered walnut shells, bran, powdered cellulose, extraction residue of vegetables, synthetic polymers such as powdered synthetic resins, inorganic mineral powder such as clays (for example, kaolin, bentonite, acid clay and the like), talcs (for example, talc, pyrophyllite and the like), silica powders or flakes (for example, diatomaceous earth, silica sand, mica, white carbon [synthetic, high-dispersion silicic acid, also called finely divided hydrated silicon, hydrated silicic acid, some of commercially available products contain calcium silicate as the major component]) activated carbon, powdered sulfur, pumice stone, calcined diatomite, brick groats, fly ash, sand, calcium carbonate powder, calcium phosphate powder and other inorganic mineral powders, chemical fertilizers (for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride and the like), compost and the like. These carriers can be used singly or in combination of two or more kinds.

A material which can be the inert liquid carrier is selected from such a material which itself has solvency or which does not have such solvency but is capable of dispersing an effective ingredient compound with the aid of an adjuvant. The following are typical examples of the carrier and can be used singly or in combination of two or more kinds. Examples thereof include water, alcohols (for example, methanol, ethanol, isopropanol, butanol, ethylene glycol and the like), ketones (for example, acetone, methylethyl ketone, methylisobutyl ketone, diisobutyl ketone, cyclohexanone and the like), ethers (for example, ethyl ether, dioxane, cellosolve, diisopropyl ether, tetrahydrofuran and the like) aliphatic hydrocarbons (for example, kerosene, mineral oil and the like), aromatic hydrocarbons (for example, benzene, toluene, xylene, solvent naphtha, alkyl naphthalene and the like), halogenated hydrocarbons (for example, dichloromethane, chloroform, carbon tetrachloride, chlorobenzene and the like), esters (for example, ethyl acetate, butyl acetate, ethyl propionate, diisobutyl phthalate, dibutyl phthalate, dioctyl phthalate and the like), amides (for example, dimethylformamide, diethylformamide, dimethylacetamide and the like) and nitriles (for example, acetonitrile and the like).

As an adjuvant, typical adjuvants mentioned below can be exemplified. These adjuvants can be used depending on purposes and used singly or in combination of two or more kinds or cannot be used at all in some cases.

To emulsify, disperse, dissolve and/or wet a compound as an active ingredient, a surfactant is used. Examples thereof include surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene resinates, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylarylsulfonates, naphthalenesulfonates, lignin sulfonates, higher alcohol sulfate esters and the like.

Furthermore, to stabilize the dispersion of a compound as an active ingredient, adhere it and/or bind it, the following adjuvants can be used. Examples thereof include casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose, gum Arabic, polyvinyl alcohols, pine oil, bran oil, bentonite, Xanthan gum, lignin sulfonates and the like.

In order to improve the fluidity of a solid product, the following adjuvants can be used. For example, adjuvants such as waxes, stearates, alkyl phosphates and the like can be used. Adjuvants such as naphthalenesulfonic acid condensation products and polycondensates of phosphates may be used as a peptizer for suspendible products. As a defoaming agent, adjuvants such as silicon oils can also be used.

Incidentally, the insecticidal and fungicidal composition of the present invention is stable to light, heat, oxidation and the like. However, an anti-oxidant or an ultraviolet absorber, for example, a phenol derivative such as BHT (2,6-di-t-butyl-4-methylphenol) and BHA (butylated hydroxyanisole), a bisphenol derivative or arylamines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, condensates of phenetidine and acetone, or a stabilizer such as a benzophenone-based compound is added in a proper amount when necessary, whereby it is possible to obtain a composition with much stabilized effect.

The weight ratio of the active compound in the present invention can be varied in a relatively wide range. The fungicidal active compound represented by the general formula (3) or (4) is contained from 0.02 to 50 weight parts and preferably from 0.1 to 20 weight parts per 1 weight part of the insecticidal active compound represented by the general formula (1) or (2). Furthermore, the content of the active ingredient of the insecticidal and fungicidal composition of the present invention is usually from 0.1 weight % to 20 weight % for dust formulation, from 5 weight % to 50 weight % for emulsifiable concentrate, from 10 weight % to 90 weight % for wettable powder, from 0.1 weight % to 20 weight % for granule, and from 10 weight % to 90 weight % for flowable formulation. On the other hand, the amount of the carrier in each formulation is usually from 60 weight % to 99 weight % for dust formulation, from 40 weight % to 95 weight % for emulsifiable concentrate, from 10 weight % to 90 weight % for wettable powder, from 80 weight % to 99 weight % for granule, and from 10 weight % to 90 weight % for flowable formulation. Meanwhile, the amount of the adjuvant is usually from 0.1 weight % to 20 weight % for dust formulation, from 1 weight % to 20 weight % for emulsifiable concentrate, from 0.1 weight % to 20 weight % for wettable powder, from 0.1 weight % to 20 weight % for granule, and from 0.1 weight % to 20 weight % for flowable formulation.

In order to control various kinds of diseases and insect pests, the insecticidal and fungicidal composition of the present invention may be applied to crops which are expected to create diseases and insect pests or places where such creation is not desired in an amount effective in controlling diseases and insect pests as intact, as appropriately diluted with water or the like, or as suspended, and used accordingly. The amount thereof is varied according to various factors such as purpose, target diseases and insect pests, reared status of crops, occurrence trend of diseases and insect pests, weather, environmental conditions, the type of formulation, method of application, place of application, time of application and the like. However, generally, the active ingredient is preferably used at a concentration of from 0.0001 to 5000 ppm and preferably from 0.01 to 1000 ppm. Furthermore, the amount of the composition applied per 10 a is generally from 1 to 500 g as the active ingredient.

The insecticidal and fungicidal composition of the present invention may be used singly for preventing various diseases and insect pests which are injurious to paddy rice, fruit trees, vegetables, other crops, flowers and the like. Also, it may be used in combination of one or more kinds of other insecticides and/or fungicides in order to obtain an excellent control effect.

When the insecticidal and fungicidal composition of the present invention is used in combination with one or more kinds of other insecticides and/or fungicides, the insecticidal and fungicidal composition of the present invention may be used as a mixed solution with other insecticides and/or fungicides, or the insecticidal and fungicidal composition of the present invention may be used as a mixture with other insecticides and/or fungicides at the time of application of the agrochemicals. In addition to the above insecticides and fungicides, the insecticidal and fungicidal composition of the present invention can be used as a mixture with a plant protection agent such as a herbicide, a fertilizer, a soil conditioner, a plant growth regulator and the like or a material, whereby a multi-purpose composition with an excellent effect can be prepared.

EXAMPLES

The typical examples for preparing the compound represented by the general formula (1) of the present invention are illustrated below with reference to the following Examples. However, the present invention is not restricted to these Examples.

Example 1-1
Preparation of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-nitrobenzamide

To a solution of 20.0 g of 2,6-dimethyl-4-heptafluoroisopropylaniline and 11.0 g of pyridine added to 100 ml of tetrahydrofuran and stirred at room temperature was introduced dropwise 13.0 g of 3-nitrobenzoyl chloride dissolved in 20 ml of tetrahydrofuran little by little. The reaction solution was stirred at room temperature for 10 hours, and then ethyl acetate and water were added thereto. Solution separation was performed for taking out an organic layer. The organic layer was dried over anhydrous magnesium sulfate. The solution was filtered off, the filtrate was collected, and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was washed with a mixed solvent of hexane and diisopropyl ether to obtain 26.0 g of the desired product (Yield: 85%) 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

To a solution of 0.90 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-nitrobenzamide and 1.56 g of anhydrous stannous chloride added to 25 ml of ethanol and stirred at room temperature was added 2 ml of concentrated hydrochloric acid, and the resulting mixture was stirred at 60 degree centigrade for 1 hour. The reaction solution was returned to room temperature, poured into water, and then neutralized with potassium carbonate. Ethyl acetate was added thereto, the insoluble substance was filtered off, and then the organic layer was separated and dried over anhydrous magnesium sulfate. The solution was filtered off, the filtrate was collected, and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was washed with hexane to obtain 0.44 g of the desired product (Yield: 53%) 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 of 0.25 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide and 0.06 g of pyridine added to 5 ml of tetrahydrofuran and stirred at room temperature was introduced dropwise 0.09 g of benzoyl chloride dissolved in 1 ml of tetrahydrofuran. The reaction solution was stirred at room temperature for 1 hour, and then ethyl acetate and 1N hydrochloric acid were added thereto for separating an organic layer. The organic layer was washed with saturated baking soda solution one time and then dried over anhydrous magnesium sulfate. The solution was filtered off, the filtrate was collected and the solvent was removed under a reduced pressure to precipitate a solid. The precipitated solid was washed with diisopropyl ether to obtain 0.29 g of the desired product (Yield: 92%) as a white solid.

¹H-NMR (DMSO-d₆, ppm) δ2.37 (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 solution of 0.18 g of 60% sodium hydride suspended in 15 ml of tetrahydrofuran was introduced dropwise 2.0 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-nitrobenzamide dissolved in 5 ml of tetrahydrofuran at room temperature. The reaction solution was stirred at room temperature for 30 minutes, and then 0.65 g of methyl iodide dissolved in 5 ml of tetrahydrofuran was introduced dropwise. Subsequently, the reaction solution was heated to 50 degree centigrade and stirred for 4 hours and then returned to room temperature, and ethyl acetate and water were added thereto. An organic layer was separated, washed with water one time, and then dried over anhydrous magnesium sulfate. The solvent was removed under a reduced pressure. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane:ethyl acetate=6:1) to obtain 1.73 g of the desired product (Yield: 84%) as a white solid.

¹H-NMR (CDCl₃, ppm) δ2.31 (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

A solution of 1.50 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl-N-methyl 3-nitrobenzamide and 0.15 g of 10% palladium carbon added to 20 ml of methanol was stirred in an ordinary pressure, in a hydrogen atmosphere for 2 hours. The catalyst was filtered out and then the solvent was removed under a reduced pressure. Subsequently, the precipitated solid was washed with hexane to obtain 1.24 g of the desired product (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)

A desired title product was prepared according to the conditions as described in Example 1-3 as a white solid.

¹H-NMR (DMSO-d₆, ppm) δ2.29 (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-chloropyridine-3-yl)carbonylamino]benzamide (Compound No. 106)

To a solution of 0.6 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide and 0.4 g of pyridine added to 10 ml of tetrahydrofuran was added 0.35 g of 2-chloronicotic acid chloride hydrochloride, and the resulting solution was stirred at room temperature for 4 hours. Ethyl acetate was added thereto and then the reaction solution was washed with saturated baking soda solution two times, and the solvent was removed under a reduced pressure. The precipitated solid was washed with a mixed solvent of hexane and diisopropyl ether and dried to obtain 0.64 g of the desired product (Yield: 75%) as a white solid.

¹H-NMR (DMSO-d₆, ppm) δ2.30 (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-[(pyridine-3-yl)carbonylamino]benzamide (Compound No. 101)

A solution of 99 mg of nicotic acid and 153 mg of 1,1′-oxalyldiimidazole added to 10 ml of acetonitrile was stirred at room temperature for 15 minutes and at 40 degree centigrade for 40 minutes. The reaction solution was returned to room temperature, and then 300 mg of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzamide was added thereto and stirred at 60 degree centigrade for 5 hours. Subsequently, the solvent was removed under a reduced pressure to obtain a residue. While ethyl was added to the resulting residue, the organic layer was washed with saturated baking soda solution two times, and the solvent was removed under a reduced pressure again. The obtained residue was purified by silica gel column chromatography using an eluent (development solvent; hexane:ethyl acetate=1:3) to obtain 70 mg of the desired product (Yield: 18%) as a white solid.

¹H-NMR (DMSO-d₆, ppm) δ2.30 (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).

Example 5-1
Preparation of N-methyl-2-bromo-4-heptafluoroisopropyl-6-methylaniline

To a solution of 1.0 g of N-methyl-4-heptafluoroisopropyl-2-methylaniline added to 5 ml of N,N-dimethylformamide was introduced dropwise 0.8 g of N-bromosuccinic acid imide dissolved in 3 ml of N,N-dimethylformamide. The resulting solution was stirred at room temperature for 5 hours, and then ethyl acetate and water were added thereto for separating an organic layer. The organic layer was washed with water two times, and then dried over anhydrous magnesium sulfate and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane:ethyl acetate=9:1) to obtain 0.86 g of the desired product (Yield: 68%) as red oil.

¹H-NMR (CDCl₃, ppm) δ2.41 (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)

A desired title product was prepared from N-methyl-2-bromo-4-heptafluoroisopropyl-6-methylaniline according to the conditions as described in Example 1 as a white solid.

¹H-NMR (DMSO-d₆, ppm) δ2.41 (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 solution of 40 mg of 60% sodium hydride suspended in 10 ml of tetrahydrofuran was introduced dropwise 0.3 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl-N-methyl 3-(benzoylamino)benzamide dissolved in 5 ml of tetrahydrofuran at room temperature. The reaction solution was stirred at room temperature for 1 hour, and then 0.16 g of methyl iodide dissolved in 5 ml of tetrahydrofuran was introduced dropwise. Subsequently, the reaction solution was heated to 50 degree centigrade, stirred for 4 hours and then returned to room temperature, and ethyl acetate and water were added thereto. An organic layer was separated and washed with water one time, and then dried over anhydrous magnesium sulfate. The solvent was removed under a reduced pressure. The resulting residue was washed with diisopropyl ether to obtain 1.73 g of the desired product (Yield: 84%) as a white solid.

¹H-NMR (DMSO-d₆, ppm) δ2.20 (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 a Lawson reagent were added to 10 ml of toluene, and the resulting solution was heated and stirred at a reflux temperature for 6 hours. The reaction solution was concentrated under a reduced pressure for removing the solvent, and then the resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane:ethyl acetate=3:1) to obtain 0.07 g of the desired product (Yield: 20%).

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)

A desired title product was prepared from N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-aminobenzthioamide according to the conditions as described in Example 1-3.

¹H-NMR (CDCl₃, ppm) δ2.38 (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 a Lawson reagent added to 10 ml of toluene was stirred at 70 degree centigrade for 6 hours. The reaction solution was concentrated under a reduced pressure, and the resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane:ethyl acetate=3:1) to prepare 0.18 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(phenylthiocarbonylamino)benzamide (Yield: 47%) and 0.05 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(phenylthiocarbonylamino)benzthioamide (Yield: 13%) respectively.

Physical Properties of Compound No. 2202

¹H-NMR (CDCl₃, ppm) δ2.36 (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).

Physical Properties of Compound No. 2203

¹H-NMR (CDCl₃, ppm) δ2.38 (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-heptafluoroisopropyl)phenyl 3-nitrobenzamide

Using N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-nitrobenzamide and benzyl bromide, a desired title product was prepared according to the method as described in Example 6.

Example 9-2
Preparation of N-benzyl-N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(2-fluorobenzoylamino)benzamide

Using N-benzyl-N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-nitrobenzamide and 2-fluorobenzoyl chloride, a desired title product was prepared according to the method as 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

Using N-benzyl-N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-(2-fluorobenzoylamino)benzamide and ethyl iodide, a desired title product was prepared according to the method as 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 added to 10 ml of methanol was stirred at 45 degree centigrade in a hydrogen atmosphere for 6 hours. The catalyst was filtered out and then the solvent was removed under a reduced pressure. Subsequently, the resulting residue was purified by silica gel (NH Silica by Fuji Silysia Chemical Ltd.) column chromatography using an eluent (development solvent; hexane:ethyl acetate=1:1) to obtain 0.30 g of the desired product (Yield: 32%) as a white solid.

¹H-NMR (DMSO-d₆, ppm) δ1.17 (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).

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 in accordance with the method as described in Example 1-1 and 0.87 g of potassium fluoride (spray drying product) were added to 25 ml of N,N-dimethylformamide dried using molecular sieves, and the mixture was heated and stirred at 150 degree centigrade for 3 hours. The reaction solution was returned to room temperature, and then ethyl acetate and water were added thereto for solution separation. An organic layer was separated, washed with water two times, and dried over anhydrous magnesium sulfate. The solution was filtered off, the filtrate was collected and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane:ethyl acetate=4:1) to obtain 1.02 g of the desired product (Yield: 45%) 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)

A desired title product was prepared according to the method as 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-dimethylformamide were introduced to 30 ml of toluene, and then 3.7 g of thionyl chloride was added thereto. The resulting solution was stirred at 80 degree centigrade for 1 hour and then stirred under a reflux condition for 2 hours. The solution was cooled down to room temperature, the solvent was removed under a reduced pressure, the resulting residue was dissolved in 10 ml of tetrahydrofuran, and 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. The solution was stirred at room temperature for 2 hours, and then ethyl acetate was introduced thereinto. The organic layer was washed successively with water and saturated baking soda solution, and dried over anhydrous magnesium sulfate. Then, the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane:ethyl acetate=4:1) to obtain 5.9 g of the desired product (Yield: 46%) as a white solid.

¹H-NMR (CDCl₃, ppm) δ2.11 (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

A desired title product was obtained according to the conditions as described in Example 1-2 as a white solid.

¹H-NMR (DMSO-d₆, ppm) δ2.26 (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 from 0 to 5 degree centigrade and stirred, and 2.50 g of N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl 3-amino-4-fluorobenzamide was added thereto. The reaction solution was stirred for 15 minutes, and then 18 ml of 37% aqueous formaldehyde solution was added dropwise thereto. The solution was stirred at 0 degree centigrade for 1 hour and at room temperature for 3 hours. To the reaction solution cooled down to 0 degree centigrade again was added 28% ammonia water for neutralization and ethyl acetate was added thereto for separating an organic layer. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane:ethyl acetate=4:1) to obtain 1.74 g of the desired product (Yield: 67%) as an amorphous substance.

¹H-NMR (CDCl₃, ppm) δ2.32 (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 can be prepared in accordance with the method as 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)

Using 4-nitrobenzoyl chloride, a desired title product was obtained according to the conditions as described in Example 1-3 as a white solid.

¹H-NMR (DMSO-d₆, ppm) δ2.23 (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 2,6-dibromo-4-heptafluoroisopropylaniline

To a solution of 2.0 g of 4-heptafluoroisopropylaniline added to 5 ml of N,N-dimethylformamide was introduced 2.73 g of N-bromosuccinic acid imide dissolved in 10 ml of N,N-dimethylformamide at 5 degree centigrade. The reaction solution was returned to room temperature and stirred for 2 hours, and then ethyl acetate and water were added thereto for separating an organic layer. The organic layer was further washed with water one time. After the solvent was removed under a reduced pressure, the resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane:ethyl acetate=20:1) to obtain 2.20 g of the desired product (Yield: 69%) as orange oil.

¹H-NMR (CDCl₃, ppm) δ4.89 (2H, broad-s), 7.59 (2H, s).

Example 12-2
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 degree centigrade for 20 hours. The resulting solution was returned to room temperature, and then ethyl acetate and 1N hydrochloric acid were added thereto. An organic layer was separated and then washed with saturated baking soda solution. The solvent was removed under a reduced pressure and the resulting residue was dissolved in a mixed solvent of 8 ml of tetrahydrofuran and 2 ml of methanol. Subsequently, the reaction solution was cooled down to 5 degree centigrade, 0.30 g of sodium hydroxide was added thereto, the mixture was stirred for 2 hours, and then ethyl acetate and water were added thereto. An organic layer was separated and washed with saturated baking soda solution, and then dried over anhydrous magnesium sulfate. The solvent was removed under a reduced pressure to obtain a residue. The resulting residue was washed with hexane to obtain 2.19 g of the desired product (Yield: 73%) as a light brown solid.

¹H-NMR (DMSO-d₆, ppm) δ7.92 (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 12-3
Preparation of N-(2,6-dibromo-4-heptafluoroisopropyl)phenyl 3-aminobenzamide

A desired title product was obtained according to the conditions as described in Example 1-2 as a white solid.

¹H-NMR (DMSO-d₆, ppm) δ5.39 (2H, broad-s), 6.77-6.80 (1H, m), 7.13-7.20 (3H, m), 8.02 (2H, s), 10.35 (1H, s).

Example 12-4
Preparation of N-(2,6-dibromo-4-heptafluoroisopropyl)phenyl 3-(2-fluorobenzoyl)aminobenzamide (Compound No. 8)

Using 2-fluorobenzoyl chloride, a desired title product was obtained according to the conditions as described in Example 1-3 as a white solid.

¹H-NMR (DMSO-d₆, ppm) δ7.33-7.40 (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 13-1
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 was added 5.91 g of 1-iodoheptafluoro-n-propane. The resulting mixture was stirred at room temperature for 3 hours, diluted with ether, and then washed with aqueous 1N sodium hydroxide solution, and purified by silica gel column chromatography using an eluent (development solvent; hexane:ethyl acetate=4:1) to obtain 1.85 g of the desired product (Yield: 63%).

¹H-NMR (CDCl₃, ppm) δ3.95 (2H, s), 6.66 (2H, d, J=8.8 Hz), 7.40 (2H, d, J=8.8 Hz).

Example 13-2
Preparation of 2,6-dibromo-4-(heptafluoro-n-propylthio)aniline

To a solution of 0.77 g of 4-(heptafluoro-n-propylthio)aniline added to 15 ml of N,N-dimethylformamide was introduced 0.98 g of N-bromosuccinic acid imide. The resulting solution was stirred at 60 degree centigrade for 2 hours, and then ether and water were added thereto for separating an organic layer. The organic layer was washed with water two times, and then dried over anhydrous magnesium sulfate. The solvent was removed under a reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane:ethyl acetate=9:1) to obtain 1.19 g of the desired product (Yield: 100%) as red oil.

¹H-NMR (CDCl₃, ppm) δ4.98 (2H, broad-s), 7.66 (2H, s).

Example 13-3
Preparation of N-{2,6-dibromo-4-(heptafluoro-n-propylthio)}phenyl 3-nitrobenzamide

To a solution of 1.08 g of 2,6-dibromo-4-(heptafluoro-n-propylthio)aniline and 0.4 g of pyridine added to 20 ml of tetrahydrofuran and stirred at room temperature was introduced dropwise 0.55 g of 3-nitrobenzoyl chloride dissolved in 20 ml of tetrahydrofuran little by little. The reaction solution was stirred at room temperature for 10 hours, and then ethyl acetate and water were added thereto. An organic layer was separated and dried over anhydrous magnesium sulfate. The solution was filtered out, the filtrate was collected, and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane:ethyl acetate=4:1) to obtain 0.86 g of the desired product (Yield: 48%) as a white solid.

¹H-NMR (CDCl₃, ppm) δ7.73 (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 13-4
Preparation of N-{2,6-dibromo-4-(heptafluoro-n-propylthio)}phenyl 3-aminobenzamide

To a solution of 0.97 g of N-{2,6-dibromo-4-(heptafluoro-n-propylthio)}phenyl 3-nitrobenzamide and 0.95 g of anhydrous stannous chloride added to 20 ml of ethanol and stirred at room temperature was added 2 ml of concentrated hydrochloric acid, and the resulting mixture was heated and stirred at 60 degree centigrade for 1 hour. The reaction solution was returned to room temperature, poured into water, and then neutralized with potassium carbonate. Ethyl acetate was added thereto, the insoluble substance was filtered out, and then an organic layer was separated and dried over anhydrous magnesium sulfate. The solution was filtered off, the filtrate was collected, and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was washed with hexane to obtain 0.75 g of the desired product (Yield: 81%) as a white solid.

¹H-NMR (CDCl₃, ppm) δ3.89 (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 13-5
Preparation of N-(2,6-dibromo-4-heptafluoro-n-propylthio)phenyl 3-(benzoylamino)benzamide (Compound No. 263)

To a solution of 0.10 g of N-(2,6-dibromo-4-heptafluoro-n-propylthio)phenyl 3-aminobenzamide and 0.02 g of pyridine added to 5 ml of tetrahydrofuran and stirred at room temperature was introduced dropwise 0.03 g of benzoyl chloride dissolved in 1 ml of tetrahydrofuran. The resulting mixture was stirred at room temperature for 1 hour, and then ethyl acetate and 1N hydrochloric acid were added thereto for separating an organic layer. The organic layer was washed with saturated baking soda solution one time and then dried over anhydrous magnesium sulfate. The solution was filtered off, the filtrate was collected, and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane:ethyl acetate=3:1) to obtain 0.10 g of the desired product (Yield: 67%) as a white solid.

¹H-NMR (CDCl₃, ppm) δ7.47-7.57 (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 13-6
Preparation of N-(2,6-dibromo-4-heptafluoro-n-propylthio)phenyl 3-[(2-chloropyridine-3-yl)carbonylamino]benzamide (Compound No. 309)

To a solution of 0.15 g of N-(2,6-dibromo-4-heptafluoro-n-propylthio)phenyl 3-aminobenzamide and 0.03 g of pyridine added to 5 ml of tetrahydrofuran was added 0.05 g of 2-chloronicotic acid chloride hydrochloride, and the mixture was stirred at room temperature for 4 hours. Ethyl acetate was added thereto, and then the solution was washed with saturated baking soda solution two times, and the solvent was removed under a reduced pressure. The precipitated solid was purified by silica gel column chromatography using an eluent (development solvent; hexane:ethyl acetate=3:1) to obtain 0.17 g of the desired product (Yield: 92%) as an amorphous substance.

¹H-NMR (CDCl₃, ppm) δ7.44 (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, 4.5 Hz).

Example 13-7
Preparation of N-(2,6-dibromo-4-heptafluoro-n-propylsulfinyl)phenyl 3-nitrobenzamide

To a solution of 0.5 g of N-(2,6-dibromo-4-heptafluoro-n-propylthio)phenyl 3-nitrobenzamide added to 15 ml of chloroform and stirred at room temperature was introduced 0.5 g of m-chloroperbenzoic acid. The mixture was stirred at room temperature for 2 days, and then an aqueous solution of sodium sulfite was added thereto and stirred. While solution separation was performed, the reaction solution was washed with aqueous sodium hydroxide solution and saturated salt water, and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane:ethyl acetate=4:1) to obtain 0.36 g of the desired product (Yield: 70%) as a white solid.

¹H-NMR (CDCl₃, ppm) δ7.76-7.82 (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 13-8
Preparation of N-(2,6-dibromo-4-heptafluoro-n-propylsulfinyl)phenyl 3-aminobenzamide

Using N-(2,6-dibromo-4-heptafluoro-n-propylsulfinyl)phenyl 3-nitrobenzamide, a desired title product was obtained according to the method as described in Example 1-2.

¹H-NMR (CDCl₃, ppm) δ6.90-6.94 (1H, m), 7.28-7.33 (3H, m), 7.73 (1H, s), 8.02 (1H, s), 8.25 (1H, s).

Example 13-9
Preparation of N-(2,6-dibromo-4-heptafluoro-n-propylsulfinyl)phenyl 3-(benzoylamino)benzamide (Compound No. 335)

Using N-(2,6-dibromo-4-heptafluoro-n-propylsulfinyl)phenyl 3-aminobenzamide, a desired title product was obtained according to the method as 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 13-10
Preparation of 2,6-dimethyl-4-heptafluoro-n-propylthioaniline

3.0 g (1.3 mmole) of 2,6-dibromo-4-heptafluoro-n-propylthioaniline, 3.0 g (21.9 mmole) of potassium carbonate, 0.75 g (0.65 mmole) of tetrakis(triphenylphosphine)palladium and 0.17 g (1.3 mmole) of trimethylboroxin were added to 20 ml of DMF, and the resulting solution was stirred at 135 degree centigrade for 6 hours. The reaction solution was returned to room temperature, and then the insoluble substance was removed with celite, and the filtrate was concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane:ethyl acetate=12:1 to 4:1) to obtain 1.17 g of the desired product (Yield: 55%) as oil.

¹H-NMR (CDCl₃, ppm) δ2.17 (6H, s), 3.86 (2H, broad-s), 7.22 (2H, s).

Example 14
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 37% aqueous formaldehyde solution, 2.0 g of 10% palladium carbon and 200 ml of ethyl acetate was stirred in an ordinary pressure, in a hydrogen atmosphere at room temperature. An insoluble substance of the reaction solution was filtered out and the filtered product was washed with ethyl acetate. The filtrate was collected and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was washed with diisopropyl ether to obtain 13.5 g of the desired product (Yield: 65%) as a white solid.

¹H-NMR (CDCl₃, ppm) δ2.35 (6H, s), 2.91 (3H, s), 6.82 (1H, d, J=7.3 Hz), 7.18-7.52 (7H, m).

Example 15-1
Preparation of 3-(benzoylamino)benzoic acid

To a solution of 1.37 g of 3-aminobenzoic acid and 0.4 g of sodium hydroxide added to 50 ml of water was added dropwise a solution of 1.41 g of benzoyl chloride and 0.4 g of sodium hydroxide dissolved in 5 ml of water under an ice bath at the same time, and the resulting mixture was stirred at room temperature for 6 hours. 1N hydrochloric acid was added to the reaction solution which was adjusted to pH 1, and then the precipitated solid was filtered off and collected to obtain 1.92 g of the desired product (Yield: 80%) as a white solid.

¹H-NMR (CDCl₃, ppm) δ7.40-7.56 (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 15-2
Preparation of 3-(benzoylamino)benzoic acid chloride

To a solution of 1.5 g of 3-(benzoylamino)benzoic acid suspended in 10 ml of toluene was added 2 ml of thionyl chloride and the resulting mixture was stirred under a reflux condition for 2 hours. The reaction solution was returned to room temperature, and then the solvent was removed under a reduced pressure to obtain 1.53 g of the desired product (Yield: 95%) as a white solid.

¹H-NMR (CDCl₃, ppm) δ7.51-7.62 (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 benzoic acids which can be easily available, the following compounds can be prepared in accordance with the methods as described in Examples 15-1 and 15-2.

3-[(2-fluorobenzoyl)amino]benzoic acid chloride
3-[(3-fluorobenzoyl)amino]benzoic acid chloride
3-[(4-fluorobenzoyl)amino]benzoic acid chloride
3-[(2-chlorobenzoyl)amino]benzoic acid chloride
3-[(3-chlorobenzoyl)amino]benzoic acid chloride
3-[(4-chlorobenzoyl)amino]benzoic acid chloride
3-[(3-cyanobenzoyl)amino]benzoic acid chloride
3-[(4-cyanobenzoyl)amino]benzoic acid chloride
3-[(2-methylbenzoyl)amino]benzoic acid chloride
3-[(3-methylbenzoyl)amino]benzoic acid chloride
3-[(4-methylbenzoyl)amino]benzoic acid chloride
3-[(2-nitrobenzoyl)amino]benzoic acid chloride
3-[(3-nitrobenzoyl)amino]benzoic acid chloride
3-[(4-nitrobenzoyl)amino]benzoic acid chloride
3-[(2-trifluoromethylbenzoyl)amino]benzoic acid chloride
3-[(3-trifluoromethylbenzoyl)amino]benzoic acid chloride
3-[(4-trifluoromethylbenzoyl)amino]benzoic acid chloride
3-[(2-trifluoromethoxybenzoyl)amino]benzoic acid chloride
3-[(3-trifluoromethoxybenzoyl)amino]benzoic acid chloride
3-[(4-trifluoromethoxybenzoyl)amino]benzoic acid chloride
3-[(2,3-difluorobenzoyl)amino]benzoic acid chloride
3-[(2,4-difluorobenzoyl)amino]benzoic acid chloride
3-[(2,5-difluorobenzoyl)amino]benzoic acid chloride
3-[(2,6-difluorobenzoyl)amino]benzoic acid chloride
3-[(3,4-difluorobenzoyl)amino]benzoic acid chloride
3-[(pyridine-3-yl)carbonylamino]benzoic acid chloride
3-[(2-fluoropyridine-3-yl)carbonylamino]benzoic acid chloride
3-[(2-chloropyridine-3-yl)carbonylamino]benzoic acid chloride
3-[(2,4-dichlorobenzoyl)amino]benzoic acid chloride
3-[(2,6-dichlorobenzoyl)amino]benzoic acid chloride
3-[(3,4-dichlorobenzoyl)amino]benzoic acid chloride
3-[(2-chloro-4-fluorobenzoyl)amino]benzoic acid chloride
3-[(4-chloro-2-fluorobenzoyl)amino]benzoic acid chloride
3-[(2-chloro-6-fluorobenzoyl)amino]benzoic acid chloride
3-[(2,3,6-trifluorobenzoyl)amino]benzoic acid chloride

Example 15-3
Preparation of N-(2,6-dimethyl-4-heptafluoro-n-propylthio)phenyl 3-(benzoylamino)benzamide (Compound No. 260)

To a solution of 0.1 g of 2,6-dimethyl-4-(heptafluoro-n-propylthio)aniline and 0.03 g of pyridine added to 5 ml of tetrahydrofuran and stirred at room temperature was introduced dropwise 0.09 g of 3-(benzoylamino)benzoic acid chloride dissolved in 1 ml of tetrahydrofuran. The resulting mixture was stirred at room temperature for 1 hour, and then ethyl acetate and 1N hydrochloric acid were added thereto for separating an organic layer. The organic layer was washed with saturated baking soda solution one time and then dried over anhydrous magnesium sulfate. The solution was filtered off, the filtrate was collected, and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane:ethyl acetate=3:1) to obtain 0.10 g of the desired product (Yield: 53%) as a white solid.

¹H-NMR (CDCl₃, 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 16-1
Preparation of 2,6-dimethyl-4-[1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline

While 24.4 g of 2,6-dimethylaniline and 50.0 g of hexafluoroacetone hydrate were mixed at room temperature, 0.5 g of p-toluenesulfonic acid monohydrate was added thereto. The reaction solution was stirred at 100 degree centigrade. After disappearance of the starting raw material was confirmed by means of TLC, to the reaction solution were added ethyl acetate and 1N aqueous sodium hydroxide solution for solution separation and extraction. Anhydrous magnesium sulfate was added to an organic layer, and the organic layer was dried and then filtered off. The filtrate was concentrated under a reduced pressure, and then hexane was added to the residue for washing. The suspension was filtered off and the resulting filtered product was vacuum-dried at room temperature to obtain 24.3 g of the desired product (Yield: 69%) in the form of powder.

¹H-NMR (CDCl₃, ppm) δ2.20 (6H, s), 3.26 (1H, broad-s), 3.76 (2H, broad-s), 7.25 (2H, s).

Example 16-2
Preparation of N-[2,6-dimethyl-4-{1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl}phenyl] 3-nitrobenzamide

At room temperature, 5.0 g of 2,6-dimethyl-4-[1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline, 3.9 g of 3-nitrobenzoyl chloride and 2.1 g of pyridine were introduced to 50 ml of tetrahydrofuran in a reaction vessel, and the resulting mixture was stirred at room temperature. After disappearance of the starting raw material was confirmed by means of TLC, to the reaction solution was added saturated baking soda solution and stirred for a while. Subsequently, ethyl acetate and water were added to the reaction solution for solution separation. Anhydrous magnesium sulfate was added to the separated organic layer, the organic layer was dried and filtered off. The filtrate was evaporated to dryness and the resulting solid was pulverized to obtain 7.5 g of the desired product (Yield: 95%) in the form of powder.

¹H-NMR (DMSO-d₆, ppm) δ2.26 (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 16-3
Preparation of N-[2,6-dimethyl-4-{1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl} 3-aminobenzamide

A solution of 8.0 g of N-[2,6-dimethyl-4-{1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl}phenyl] 3-nitrobenzamide and 0.8 g of 10% palladium carbon added to 50 ml of methanol was stirred in a hydrogen atmosphere at room temperature. After disappearance of the starting raw material was confirmed by means of TLC, the reaction solution was filtered off and the obtained filtrate was concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane:ethyl acetate=3:1) to obtain 6.3 g of the desired product (Yield: 85%) in the form of powder.

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 16-4
Preparation of N-[2,6-dimethyl-4-{1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl}phenyl] 3-(benzoylamino)benzamide

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 disappearance of the starting raw material was confirmed by means of TLC, the reaction solution was filtered off and the obtained filtrate was concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane:ethyl acetate=3:1) to obtain 6.3 g of the desired product (Yield: 85%) in the form of powder.

¹H-NMR (DMSO-d₆, ppm) δ2.26 (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 was prepared according to Example 16-4.

¹H-NMR (DMSO-d₆, ppm) δ2.34 (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 16-5
Preparation of N-[2,6-dimethyl-4-{1-chloro-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl} 3-(benzoylamino)benzamide

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. Thereafter, the mixture was heated and stirred under a reflux condition. After disappearance of the starting raw material was confirmed by means of TLC, the reaction solution was cooled down and concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane:ethyl acetate=3:1) to obtain 6.2 g of the desired product (Yield: 75%) in the form of powder.

¹H-NMR (DMSO-d₆, ppm) δ2.34 (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 16-6
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)ethyl}phenyl] 3-(benzoylamino)benzamide and 165 mg of potassium fluoride were introduced to 20 ml of N,N-dimethylformamide. Thereafter, the mixture was heated to 120 degree centigrade and stirred for 4 hours. After the reaction solution was cooled down to room temperature, ethyl acetate and water were added thereto for separating an organic layer. Anhydrous magnesium sulfate was added thereto, the organic layer was dried and filtered off, and the filtrate was concentrated under a reduced pressure. The resulting residue was washed with diisopropyl ether. The suspension was filtered off and the obtained filtered product was vacuum-dried at room temperature to obtain 250 mg of the desired product (Yield: 85%) in the form of powder. The physical properties were described in Example 1-3.

Example 16-7
Preparation of N-[2,6-dimethyl-4-{1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl}phenyl] 3-(benzoylamino)benzamide

At room temperature, 2.0 g of 2,6-dimethyl-4-[1-hydroxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline, 2.7 g of 3-(benzoylamino)benzoyl chloride and 1.2 g of pyridine were introduced to 50 ml of tetrahydrofuran, and the resulting solution was stirred at room temperature. After disappearance of the starting raw material was confirmed by means of TLC, saturated baking soda solution was added to the reaction solution and the mixture was stirred for a while. Ethyl acetate and water were added to the reaction solution for solution separation. To the separated organic layer was added anhydrous magnesium sulfate, and the organic layer was dried and filtered off. The filtrate was evaporated to dryness under a reduced pressure and the resulting solid was pulverized to obtain 3.4 g of the desired product (Yield: 95%) in the form of powder. The physical properties were described in Example 16-4.

Example 16-8
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. Next, 480 mg of 2,2-difluoro-1,3-dimethyl-2-imidazolidinone was added dropwise thereto and stirred at room temperature for 8 hours. Water was added to the reaction solution and an organic layer was separated. Anhydrous magnesium sulfate was added thereto, and the organic layer was dried and filtered off. The obtained filtrate was evaporated to dryness under a reduced pressure and the resulting solid was pulverized to obtain 180 mg of the desired product (Yield: 60%) in the form of powder. The physical properties were described in Example 1-3.

Next, typical formulation examples of the present invention will be illustrated. However, the present invention is not restricted to these formulation examples. Incidentally, in the formulation examples, part(s) refers to weight part(s).

Formulation Example 1

30 parts of the compound (3006), 3 parts of the compound (1245) 22 parts of bentonite, 42 parts of talc and 3 parts of Sorpol 5060 (a surfactant, a product of Toho Chemical Industry, Co., Ltd., product name) were uniformly kneaded, granulated using a basket granulating machine, and then dried to obtain 100 parts of a granule.

Formulation Example 2

2 parts of the compound (1217), 15 parts of the compound (3003), 58 parts of bentonite, 21 parts of talc, 1 part of dodecylbenzenesulfonic acid soda, 1 part of polyoxyethylene alkylaryl ether and 2 parts of lignin sulfonic acid soda were added, uniformly kneaded, granulated using a basket granulating machine, and then dried to obtain 100 parts of a granule.

Formulation Example 3

10 parts of the compound (639), 30 parts of the compound (3007), 40 parts of diatomaceous earth, 5 parts of Sorpol 5039 (a mixture of an anionic surfactant and white carbon, a product of Toho Chemical Industry, Co., Ltd., product name) and 15 parts of white carbon were uniformly mixed and pulverized to obtain a wettable powder.

Formulation Example 4

30 parts of the compound (3004), 20 parts of the compound (3001), 43 parts of kaolinite, 5 parts of Sorpol 5039 (a mixture of an anionic surfactant and white carbon, a product of Toho Chemical Industry, Co., Ltd., product name) and 2 parts of white carbon were uniformly mixed and pulverized to obtain a wettable powder.

Formulation Example 5

10 parts of the compound (601), 5 parts of Sorpol 3074 (a nonionic surfactant, a product of Toho Chemical Industry, Co., Ltd., product name), 5 parts of a 1% aqueous solution of Xanthan gum, 40 parts of water and 10 parts of ethylene glycol were uniformly dissolved. Subsequently, 30 parts of the compound (3008) were added thereto and the resulting mixture was well stirred, followed by wet grinding with a sand mill to obtain a flowable formulation.

Formulation Example 6

5 parts of the compound (3005), 0.5 part of the compound (210), 94.3 parts of clay and 0.2 part of Driless A were uniformly mixed to obtain a powder formulation.

Furthermore, to make sure that the insecticidal and fungicidal composition of the present invention has excellent insecticidal and fungicidal activities, the following test examples are illustrated. However, the present invention is not restricted to these test examples.

Test Example 1
Insecticidal Test on Rice Striped Stem Borer (Chilo suppressalis) and Control Test on Rice Blast (Pyricularia oryzae) by Nursery Box Application of Paddy Rice

Rice (cultivar: koshihikari) cultured in a nursery box was treated with a granule formulation of a prescribed amount, and then 4 seedlings thereof planted in a 1/5000a pot were transplanted to 8 pots. After 14 days from the treatment, canopies in 4 pots were cut and put into a plastic cup (diameter: 10 cm, height: 10 cm) along with 10 two-year-old larvae of Chilo suppressalis. After 4 days, the mortality was examined (4 replications). Furthermore, after 30 days from the treatment, the other 4 pots were put into an artificial weather chamber (set condition: 25 degree centigrade, 12-12 hr light-dark cycle), and a spore suspension of Pyricularia oryzae was spray-inoculated. The humidity at the weather chamber was kept high and, after 7 days, the number of Pyricularia oryzae lesions was examined. The control value was calculated according to the following equation (4 replications). The results are shown in Table 10. In the Table, gai represents the amount of active ingredients (g).

Control Value=(1−number of lesions in the treated area/number of lesions in the untreated area)×100

TABLE 10

Pyricu-

Amount of

laria

treated

oryzae

chemical
Mortality
Control

Supplied chemical
(gai/box)
(%)
value

Compound 106 + Compound 3003
5 + 15
100
100

Compound 106 + Compound 3004
5 + 15
100
100

Compound 106 + Compound 3005
5 + 15
100
100

Compound 106 + Compound 3006
5 + 7.5
100
100

Compound 106 + Compound 3007
5 + 7.5
100
100

Compound 106 + Compound 3008
5 + 7.5
100
100

Compound 1217 + Compound 3003
5 + 15
100
100

Compound 1217 + Compound 3004
5 + 15
100
100

Compound 1217 + Compound 3005
5 + 15
100
100

Compound 1217 + Compound 3006
5 + 7.5
100
100

Compound 1217 + Compound 3007
5 + 7.5
100
100

Compound 1217 + Compound 3008
5 + 7.5
100
100

Compound 1245 + Compound 3003
5 + 15
100
100

Compound 1245 + Compound 3004
5 + 15
100
100

Compound 1245 + Compound 3005
5 + 15
100
100

Compound 1245 + Compound 3006
5 + 7.5
100
100

Compound 1245 + Compound 3007
5 + 7.5
100
100

Compound 1245 + Compound 3008
5 + 7.5
100
100

Compound 639 + Compound 3003
5 + 15
100
100

Compound 639 + Compound 3004
5 + 15
100
100

Compound 639 + Compound 3005
5 + 15
100
100

Compound 639 + Compound 3006
5 + 7.5
100
100

Compound 639 + Compound 3007
5 + 7.5
100
100

Compound 639 + Compound 3008
5 + 7.5
100
100

Compound 1246 + Compound 3003
5 + 15
100
100

Compound 1246 + Compound 3004
5 + 15
100
100

Compound 1246 + Compound 3005
5 + 15
100
100

Compound 1246 + Compound 3006
5 + 7.5
100
100

Compound 1246 + Compound 3007
5 + 7.5
100
100

Compound 1246 + Compound 3008
5 + 7.5
100
100

Compound 106
5
95
4

Compound 1217
5
95
0

Compound 1245
5
97.5
5

Compound 639
5
95
5

Compound 1246
5
97.5
0

Compound 3003
15
0
100

Compound 3004
15
0
100

Compound 3005
15
0
100

Compound 3006
7.5
0
100

Compound 3007
7.5
0
100

Compound 3008
7.5
0
100

Untreated plot

0
0

Test Example 2
Insecticidal Test on Rice Striped Stem Borer (Chilo suppressalis) and Control Test on Rice Blast (Pyricularia oryzae) by Submerged Application of Paddy Rice

A granule formulation of a prescribed amount was used in a submerged application for 4 pots of 1/5000a rice (cultivar: koshihikari; 4 leaf stage) pots. After 7 days from the treatment, canopies in 2 pots were cut and put into a plastic cup (diameter: 10 cm, height: 10 cm) along with 10 two-year-old larvae of Chilo suppressalis. After 4 days, the mortality was examined (2 replications). Furthermore, after 14 days from the treatment, the other 2 pots were put into an artificial weather chamber (set condition: 25 degree centigrade, 12-12 hr light-dark cycle), and a spore suspension of Pyricularia oryzae was spray-inoculated. The humidity at the weather chamber was kept high and, after 7 days, the number of Pyricularia oryzae lesions was examined. The control value was calculated according to the following equation (2 replications). The results are shown in Table 11. In the Table, gai represents the amount of active ingredients (g).

Control Value=(1−number of lesions in the treated area/number of lesions in the untreated area)×100

TABLE 11

Pyricu-

laria

Amount of

oryzae

treated
Mortality
Control

Supplied chemical
chemical
(%)
value

(gai/10a)

Compound 106 + Compound 3003
300 + 450
100
100

Compound 106 + Compound 3004
300 + 450
100
100

Compound 106 + Compound 3005
300 + 450
100
100

Compound 106 + Compound 3006
300 + 225
100
100

Compound 106 + Compound 3007
300 + 225
100
100

Compound 106 + Compound 3008
300 + 225
100
100

Compound 1217 + Compound 3003
300 + 450
100
100

Compound 1217 + Compound 3004
300 + 450
100
100

Compound 1217 + Compound 3005
300 + 450
100
100

Compound 1217 + Compound 3006
300 + 225
100
100

Compound 1217 + Compound 3007
300 + 225
100
100

Compound 1217 + Compound 3008
300 + 225
100
100

Compound 1245 + Compound 3003
300 + 450
100
100

Compound 1245 + Compound 3004
300 + 450
100
100

Compound 1245 + Compound 3005
300 + 450
100
100

Compound 1245 + Compound 3006
300 + 225
100
100

Compound 1245 + Compound 3007
300 + 225
100
100

Compound 1245 + Compound 3008
300 + 225
100
100

Compound 639 + Compound 3003
300 + 450
100
100

Compound 639 + Compound 3004
300 + 450
100
100

Compound 639 + Compound 3005
300 + 450
100
100

Compound 639 + Compound 3006
300 + 225
100
100

Compound 639 + Compound 3007
300 + 225
100
100

Compound 639 + Compound 3008
300 + 225
100
100

(gai/box)

Compound 1246 + Compound 3003
300 + 450
100
100

Compound 1246 + Compound 3004
300 + 450
100
100

Compound 1246 + Compound 3005
300 + 450
100
100

Compound 1246 + Compound 3006
300 + 225
100
100

Compound 1246 + Compound 3007
300 + 225
100
100

Compound 1246 + Compound 3008
300 + 225
100
100

Compound 106
300
90
3

Compound 1217
300
95
5

Compound 1245
300
95
0

Compound 639
300
90
0

Compound 1246
300
95
4

Compound 3003
450
0
100

Compound 3004
450
0
100

Compound 3005
450
0
100

Compound 3006
225
0
100

Compound 3007
225
5
100

Compound 3008
225
0
100

Untreated plot

0
0

Test Example 3
Insecticidal Test on Rice Striped Stem Borer (Chilo suppressalis) and Control Test on Rice Blast (Pyricularia oryzae) of Paddy Rice

A liquid chemical which was prepared to the prescribed concentration was sprayed on 4 pots of rice (cultivar: koshihikari; 4 leaf stage) pots. After air-drying, canopies in 2 pots were cut and put into a plastic cup (diameter: 10 cm, height: 10 cm) along with 10 two-year-old larvae of Chilo suppressalis. After 4 days, the mortality was examined (2 replications). Furthermore, after 1 day from spraying, the other 2 pots were put into an artificial weather chamber (set condition: 25 degree centigrade, 12-12 hr light-dark cycle), and a spore suspension of Pyricularia oryzae was spray-inoculated. The humidity at the weather chamber was kept high and, after 7 days, the number of Pyricularia oryzae lesions was examined. The control value was calculated according to the following equation (2 replications). The results are shown in Table 12.

Control Value=(1−number of lesions in the treated area/number of lesions in the untreated area)×100

TABLE 12

Pyricu-

laria

Amount of

oryzae

treated
Mortality
Control

Supplied chemical
chemical
(%)
value

(gai/10a)

Compound 601 + Compound 3003
100 + 150
100
100

Compound 601 + Compound 3004
100 + 150
100
100

Compound 601 + Compound 3005
100 + 150
100
100

Compound 601 + Compound 3006
100 + 60
100
100

Compound 601 + Compound 3007
100 + 60
100
100

Compound 601 + Compound 3008
100 + 60
100
100

Compound 1208 + Compound 3003
100 + 150
100
100

Compound 1208 + Compound 3004
100 + 150
100
100

Compound 1208 + Compound 3005
100 + 150
100
100

Compound 1208 + Compound 3006
100 + 60
100
100

Compound 1208 + Compound 3007
100 + 60
100
100

Compound 1208 + Compound 3008
100 + 60
100
100

Compound 210 + Compound 3003
100 + 150
100
100

Compound 210 + Compound 3004
100 + 150
100
100

Compound 210 + Compound 3005
100 + 150
100
100

Compound 210 + Compound 3006
100 + 60
100
100

Compound 210 + Compound 3007
100 + 60
100
100

Compound 210 + Compound 3008
100 + 60
100
100

Compound 3000 + Compound 3003
100 + 150
100
100

Compound 3000 + Compound 3004
100 + 150
100
100

Compound 3000 + Compound 3005
100 + 150
100
100

Compound 3000 + Compound 3006
100 + 60
100
100

Compound 3000 + Compound 3007
100 + 60
100
100

Compound 3000 + Compound 3008
100 + 60
100
100

(gai/box)

Compound 3001 + Compound 3003
100 + 150
100
100

Compound 3001 + Compound 3004
100 + 150
100
100

Compound 3001 + Compound 3005
100 + 150
100
100

Compound 3001 + Compound 3006
100 + 60
100
100

Compound 3001 + Compound 3007
100 + 60
100
100

Compound 3001 + Compound 3008
100 + 60
100
100

Compound 3002 + Compound 3003
100 + 150
100
100

Compound 3002 + Compound 3004
100 + 150
100
100

Compound 3002 + Compound 3005
100 + 150
100
100

Compound 3002 + Compound 3006
100 + 60
100
100

Compound 3002 + Compound 3007
100 + 60
100
100

Compound 3002 + Compound 3008
100 + 60
100
100

Compound 601
100
95
2

Compound 1208
100
95
5

Compound 210
100
95
0

Compound 3000
100
90
3

Compound 3001
100
95
0

Compound 3002
100
90
3

Compound 3003
150
0
100

Compound 3004
150
0
100

Compound 3005
150
0
100

Compound 3006
60
0
100

Compound 3007
60
5
100

Compound 3008
60
0
100

Untreated plot

0
0

Insecticidal and fungicidal composition

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