PESTICIDAL DIARYL - HETEROCYCLYL DERIVATIVES

The present invention relates to novel pesticidal allylAryl heterocycle derivatives and use thereof as pesticides.

In Patent Documents 1 to 4, it is described that some kinds of 5-membered heterocyclic compounds or nitrogen-containing heterocyclic compounds are useful as an agent for controlling harmful organisms.

[Prior Art Literatures]

WO 2007/123853, Japanese Patent Publication No. 2008-110971, WO 2010/020522, WO 2010/043315.

[Summary of the Invention]

Inventors of the present invention conducted extensive research to develop a novel compound which is highly effective as pesticides and has a broad spectrum of use. As a result, the inventors found that the novel allylAryl heterocycle derivatives represented by the following Formula (I), and N-oxide and salts thereof have a high activity, a broad spectrum of use and safety, and also are effective against harmful insects that are resistant to an organic phosphorous agent or a carbamate agent.

In the formula, R' represents Ci-12 alkyl or Ci-12 haloalkyl,

1 represents 0 or 1,

U represents CH ₂ , S=0 or S0 ₂ ,

Ai, A2, A3 and A4 each independently represent C-Y or N, with the proviso that two of Ai, A2, A3 and A4 may simultaneously represent N, or two Ys may form, together with the carbon atom to which they are bound, a benzene ring or a 5- to 6-membered heteroaromatic ring when Ai and A2 represent C-Y,

Bi, B2, B3 and B4 each independently represent C-X or N,

L represents (CR'R ² ),!, n represents 1, 2 or 3, R ¹ and R ² each independently represent hydrogen, cyano, Ci-12 alkyl, C3-8 cycloalkyl, C3-8 cycloalkyl-Ci-12 alkyl, C2-6 alkenyl, C2-6 alkynyl, Ci-12 alkoxy-carbonyl or Ci-12 thioalkoxy-carbonyl, and herein, each group from Ci-12 alkyl to Ci-12 thioalkoxy-carbonyl above may be optionally substituted with halogen, or R ¹ and R ² may form, together with the carbon atom to which they are bound, a 3- to 6- membered hydrocarbon ring, or R ¹ may form, together with Y of A2, C2-3 alkylene when n represents 1 and A2 represents C-Y,

R ³ represents hydrogen, amino, hydroxy, cyano, Ci-12 alkyl, Ci-12 alkoxy, Ci-12 alkyl- carbonylamino, Ci-12 alkylamino, C3-8 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, Ci-12 alkyl-carbonyl, -CH2- R ⁵ , -C(=0)R ⁵ or C(=S)R ⁵ , and herein, each group from Ci-12 alkyl to Ci-12 alkyl-carbonyl above may be optionally substituted,

R ⁴ represents hydrogen, cyano, formyl, thioformyl, Ci-12 alkyl-carbonyl, Ci-12 alkyl- thiocarbonyl, Ci-12 alkylamino-carbonyl, Ci-12 alkylamino-thiocarbonyl, C2-24 (total carbon number) dialkylamino-carbonyl, C2-24 (total carbon number) dialkylamino-thiocarbonyl, Ci-12 alkoxyamino- carbonyl, Ci-12 alkoxyamino-thiocarbonyl, Ci-12 alkoxy-carbonyl, Ci-12 alkoxy-Ci-12 alkyl-carbonyl, Ci-12 thioalkoxy-Ci-12 alkyl-carbonyl, Ci-12 alkylsulfenyl-Ci-12 alkyl-carbonyl, Ci-12 alkylsulfonyl-Ci-12 alkyl- carbonyl, Ci-12 alkoxy-thiocarbonyl, Ci-12 thioalkoxy-carbonyl, Ci-12 thioalkoxy-thiocarbonyl, Ci-12 alkylsulfonyl, C3-8 cycloalkyl-carbonyl, C3-8 cycloalkyl-Ci-12 alkyl-carbonyl, C2-12 alkenyl-carbonyl, C2-12 alkynyl-carbonyl, C3-8 cycloalkylamino-carbonyl, C2-12 alkenylamino-carbonyl, C2-12 alkynylamino- carbonyl, -C(=0)R ⁵ or C(=S)R ⁵ , and herein, each group from Ci-12 alkyl-carbonyl to C2-12 alkynylamino- carbonyl above may be optionally substituted, or R ³ and R ⁴ may form, together with the nitrogen atom to which they are bound, a 3- to 6- membered heterocycle, and herein, the heterocycle may be optionally substituted with X, keto, thioketo, or nitroimino, X and Y, which may be the same or different from each other, represent hydrogen, halogen, nitro, cyano, hydroxy, mercapto, SF5, amino, Ci-12 alkyl, C3-8 cycloalkyl, Ci-12 alkoxy, Ci-12 alkylthio, Ci- 12 alkylsulfinyl, Ci-12 alkylsulfonyl, Ci-12 alkylsulfonyloxy, Ci-12 alkylaminosulfonyl, C2-24 (total carbon number) dialkylaminosulfonyl, Ci-12 alkylcarbonylamino, benzoylamino, tri(Ci-i2 alkyl)silyl, Ci-12 alkoxyimino, Ci-12 alkylsulfinylimino, Ci-12 alkylsulfonylimino, Ci-12 alkoxy-carbonyl, Ci-12 alkylcarbonyl, aminocarbonyl, Ci-12 alkylamino-carbonyl, amino-thiocarbonyl, Ci-12 alkylamino- thiocarbonyl, C2-24 (total carbon number) dialkylamino-carbonyl or C2-24 (total carbon number) dialkylamino-thiocarbonyl, and herein, each group from Ci-12 alkyl to C2-24 (total carbon number) dialkylamino-thiocarbonyl above may be optionally substituted, and R ⁵ represents a phenyl group which may be optionally substituted or a 5- to 6-membered heterocyclic group that contains at least one hetero atom optionally selected from N, O, and S and may be optionally substituted.

[Detailed Description of The preferred Enbodiments]

For the descriptions hereinbelow, unless specifically described otherwise, definition of the symbols in each formula has the same meanings as those described above.

The compounds having the Formula (I) of the present invention can be prepared according to the following preparation method (a) and/or (b).

Preparation method (a)

A method of reacting the compounds that are represented by the following formula

Formula (Int. 1):

with the compounds that are represented by the following formula in an appropriate diluent, if necessary, in the presence of a base.

Formula (Int. 2):

In the above formula, Li independently represents halogen or C haloalkylsulfonyloxy, or two Li represent =0 when U represents CEb.

Preparation method (b) : A method of oxidizing the compounds that are represented by the following formula with an appropriate oxidizing agent, if necessary, in the presence of a catalyst when U is S0 ₂ . -2):

(1-2) In the present specification, the term "alkyl" indicates linear or branched Ci-12 alkyl, for example, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl and the like, preferably Ci-6 alkyl, and more preferably C alkyl. In addition, for an alkyl moiety that is included as a part of the constitution in other groups, those described in the above for the "alkyl" can be also exemplified.

The term "alkyl substituted with halogen" means "haloalkyl" and it indicates a carbon chain in which at least one hydrogen on linear or branched Ci-12 alkyl, preferably Ci-6 alkyl, and more preferably C alkyl is substituted with a halogen(s), for example, CH2F, CHF2, CF3, CF2CI, CFCI2, CF2Br, CF2CF3, CFHCF3, CH2CF3, CFCICF3, CCI2CF3, CF2CH3, CF2CH2F, CF2CHF2, CF2CF2CI, CF ₂ CF ₂ Br, CFHCH3, CFHCHF2, CFHCHF2, CHFCF3, CHFCF2CI, CHFCF ₂ Br, CFCICF3, CCI2CF3, CF ₂ CF ₂ CF ₃ , CH2CF2CF3, CF2CH2CF3, CF2CF2CH3, CHFCF2CF3, CF2CHFCF3, CF2CF2CHF2, CF2CF2CH2F, CF2CF2CF2CI, CF ₂ CF ₂ CF ₂ Br, CH(CHF ₂ )CF ₃ , CH(CF ₃ )CF ₃ , CF(CF ₃ )CF ₃ , CF(CF ₃ )CF ₂ Br, CF2CF2CF2CF3, CH(CF ₃ )CF ₂ CF ₃ or CF(CF ₃ )CF ₂ CF ₃ . Perfluoroalkyls in which each substitutable hydrogen on alkyl is substituted with fluorine are also included. The haloalkyl may be further substituted.

The term "alkoxy" indicates linear or branched Ci-12, preferably C e, and more preferably C alkoxy, for example, methoxy, ethoxy, n-propoxy, i-propoxy, n-, iso-, sec- or tert-butoxy, pentyloxy, or hexyloxy. The alkoxy may be further substituted. The term "halogen" and the halogen moiety in a group which is substituted with halogen represent fluorine, chlorine, bromine, and iodine, preferably fluorine, chlorine and bromine.

The term "cycloalkyl" represents C3-8 cycloalkyl including cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl, preferably C3-7 cycloalkyl, and more preferably C3-6 cycloalkyl.

In addition, for a cycloalkyl moiety that is included as a part of the constitution in other groups, those described in the above for the "cycloalkyl" can be also exemplified.

The term " cycloalkyl substituted with halogen" represents "halocycloalkyl" including fluorocyc lopropyl, chlorocyc lopropyl, difluorocyc lopropyl, dichlorocyc lopropyl, and undecafluorocyclohexyl.

The term "alkenyl" represents C2-12 alkenyl, preferably C2-5 alkenyl including vinyl, allyl, 1 - propenyl, 1 - (or 2-, or 3-) butenyl, 1 -pentenyl and the like, and more preferably C2-4 alkenyl. The term "alkynyl" represents C2-12 alkynyl, preferably C2-5 alkynyl including ethynyl, propargyl, 1-propynyl, butan-3-ynyl, pentan-4-ynyl and the like, and more preferably C2-4 alkynyl.

The term "heterocycle" represents a 5- or 6-membered heterocyclic group which contains at least one of N, O and S as a hetero atom. The cycle represents a fused heterocyclic group which may be benzo-fused and the carbon atom of the cycle may be substituted with oxo or thioxo.

Specific examples of the heterocycle include pyrrolidinyl, piperidinyl, morpholinyl, and thiomorpholinyl (examples of the saturated), dihydropyrrolyl, dihydroisoxazolyl, dihydropyrazolyl, dihydrooxazolyl, dihydrothiazolyl (examples of the partially saturated), furyl, thienyl, pyrrolyl, isoxazolyl, pyrazolyl, oxazolyl, isothiazolyl, thiazolyl, imidazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, benzoxazolyl, benzothiazolyl, quinolyl and the like. The heterocycle may be further substituted with any substituent group.

With respect to the compounds having the Formula (I) of the present invention, examples of the preferred compounds include the followings.

R' represents Ci-6 alkyl or Ci-6 haloalkyl,

Ai, A2, A3 and A4 each independently represent C-Y or N,

Bi, B2, B3 and B4 each independently represent C-X or N,

X and Y each independently represent hydrogen, halogen, nitro, cyano, hydroxy, mercapto, amino, SF5, Ci-6 alkyl, C3-7 cycloalkyl, Ci-6 alkoxy, Ci-6 alkylthio, Ci-6 alkylsulfinyl, Ci-6 alkylsulfonyl, Ci-6 alkylsulfonyloxy, Ci-6 alkylaminosulfonyl, di(Ci-6 alkyl)amino-sulfonyl, Ci-6 alkyl-carbonylamino, benzoylamino, tri(Ci-6 alkyl)silyl, Ci-6 alkoxyimino, Ci-6 alkylsulfinylimino, Ci-6 alkylsulfonylimino, Ci- 6 alkoxy-carbonyl, Ci-6 alkyl-carbonyl, aminocarbonyl, Ci-6 alkylamino-carbonyl, amino thiocarbonyl, Ci-6 alkylamino-thiocarbonyl, di(Ci_6 alkyl)amino-carbonyl or di(Ci_6 alkyl)amino-thiocarbonyl, and herein, each group from Ci-6 alkyl to di(Ci_6 alkyl)amino-thiocarbonyl above may be optionally substituted with halogen,

R ¹ and R ² each independently represent hydrogen, cyano, Ci-6 alkyl, C3-7 cycloalkyl, C3-7 cycloalkyl-Ci-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, Ci-6 alkoxy-carbonyl or Ci-6 thioalkoxy-carbonyl, and herein, each group from Ci-6 alkyl to Ci-6 thioalkoxy-carbonyl above may be optionally substituted with halogen, or R ¹ and R ² may form, together with the carbon atom to which they are bound, a 3- to 6- membered hydrocarbon ring, or R ¹ may form, together with Y of A2, C2-3 alkylene when n represents 1 and A2 represents C-Y,

R ³ represents hydrogen, amino, hydroxy, cyano, Ci-6 alkyl, Ci-6 alkoxy , Ci-6 alkyl- carbonylamino, Ci-6 alkylamino, C3-7 cycloalkyl, C2-6 alkenyl, C2-6 alkynyl, Ci-6 alkyl-carbonyl, -CH2-R ⁵ , -C(=0)R ⁵ or C(=S)R ⁵ , and herein, each group from Ci-6 alkyl to Ci-6 alkyl-carbonyl above may be optionally substituted with halogen,

R ⁴ represents hydrogen, cyano, formyl, thioformyl, Ci-6 alkyl-carbonyl, Ci-6 alkyl-thiocarbonyl, Ci-6 alkylamino-carbonyl, Ci-6 alkylamino-thiocarbonyl, di(Ci_6 alkyl)amino-carbonyl, di(Ci_6 alkyl)amino-thiocarbonyl, Ci-6 alkoxyamino-carbonyl, Ci-6 alkoxyamino-thiocarbonyl, Ci-6 alkoxy- carbonyl, Ci-6 alkoxy-Ci-6 alkyl-carbonyl, Ci-6 thioalkoxy-Ci-6 alkyl-carbonyl, Ci-6 alkylsulfenyl-Ci-6 alkyl-carbonyl, Ci-6 alkylsulfonyl-Ci-6 alkyl-carbonyl, Ci-6 alkoxy-thiocarbonyl, Ci-6 thioalkoxy- carbonyl, Ci-6 thioalkoxy-thiocarbonyl, Ci-6 alkylsulfonyl, C3-7 cycloalkyl-carbonyl, C3-7 cycloalkyl-Ci-6 alkyl-carbonyl, C2-6 alkenyl-carbonyl, C2-6 alkynyl-carbonyl, C3-7 cycloalkylamino-carbonyl, C2-6 alkenylamino-carbonyl, C ₂ -6 alkynylamino-carbonyl, -C(=0)R ⁵ or C(=S)R ⁵ , and herein, each group from Ci-6 alkyl-carbonyl to C2-6 alkynylamino-carbonyl above may be optionally substituted with halogen, and

R ⁵ represents a phenyl group which may be optionally substituted or a 5- to 6-membered heterocyclic group that contains at least one hetero atom optionally selected from N, O, and S and may be optionally substituted.

Among the compounds having the Formula (I), examples of the particularly preferred compounds include the followings.

R' represents C alkyl or C haloalkyl,

Ai, A2, A3 and A4 each independently represent C-Y or N,

Bi, B2, B3 and B4 each independently represent C-X or N,

X and Y each independently represent hydrogen, halogen, nitro, cyano, hydroxy, mercapto, amino, SF5, CM alkyl, C3-6 cycloalkyl, CM alkoxy, CM alkylthio, CM alkylsulfinyl, CM alkylsulfonyl, CM alkylsulfonyloxy, C alkylaminosulfonyl, di(Ci- ₄ alkyl)amino-sulfonyl, C alkyl-carbonylamino, benzoylamino, tri(Ci_4 alkyl)silyl, CM alkoxyimino, CM alkylsulfinylimino, CM alkylsulfonylimino, Ci_ 4 alkoxy-carbonyl, Ci _-4 alkyl-carbonyl, aminocarbonyl, CM alkylamino-carbonyl, amino thiocarbonyl, CM alkylamino-thiocarbonyl, di(Ci _-4 alkyl)amino-carbonyl or di(Ci_4 alkyl)amino-thiocarbonyl, and herein, each group from C alkyl to di(Ci_4 alkyl)amino-thiocarbonyl above may be optionally substituted with halogen,

R ¹ and R ² each independently represent hydrogen, cyano, C alkyl, C3-6 cycloalkyl, C3-6 cycloalkyl-Ci-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, CM alkoxy-carbonyl or CM thioalkoxy-carbonyl, and herein, each group from CM alkyl to CM thioalkoxy-carbonyl above may be optionally substituted with halogen, or R ¹ and R ² may form, together with the carbon atom to which they are bound, a 3- to 6- membered hydrocarbon ring, or R ¹ may form, together with Y of A2, C2-3 alkylene when n represents 1 and A2 represents C-Y,

R ³ represents hydrogen, amino, hydroxy, cyano , CM alkyl, CM alkoxy, CM alkyl- carbonylamino, CM alkylamino, C3-6 cycloalkyl, C2-4 alkenyl, C2-4 alkynyl, CM alkyl-carbonyl, -CH2-R ⁵ , -C(=0)R ⁵ or C(=S)R ⁵ , and herein, each group from CM alkyl to CM alkyl-carbonyl above may be optionally substituted with halogen,

R ⁴ represents hydrogen, cyano, formyl, thioformyl, CM alkyl-carbonyl, CM alkyl-thiocarbonyl, CM alkylamino-carbonyl, CM alkylamino-thiocarbonyl, di(Ci- ₄ alkyl)amino-carbonyl, di(Ci _-4 alkyl)amino-thiocarbonyl, Ci _-4 alkoxyamino-carbonyl, CM alkoxyamino-thiocarbonyl, CM alkoxy- carbonyl, Ci-4 alkoxy-Ci-4 alkyl-carbonyl, CM thioalkoxy-Ci-4 alkyl-carbonyl, CM alkylsulfenyl-Ci-4 alkyl-carbonyl, CM alkylsulfonyl-Ci-4 alkyl-carbonyl, CM alkoxy-thiocarbonyl, CM thioalkoxy- carbonyl, Ci-4 thioalkoxy-thiocarbonyl, CM alkylsulfonyl, C3-6 cycloalkyl-carbonyl, C3-6 cycloalkyl-Ci-4 alkyl-carbonyl, C2-4 alkenyl-carbonyl, C2-4 alkynyl-carbonyl, C3-6 cycloalkylamino-carbonyl, C2-4 alkenylamino-carbonyl, C ₂ - ₄ alkynylamino-carbonyl, -C(=0)R ⁵ or C(=S)R ⁵ , and herein, each group from CM alkyl-carbonyl to C2-4 alkynylamino-carbonyl above may be optionally substituted with halogen, and

R ⁵ represents a phenyl group which may be optionally substituted or a 5- to 6-membered heterocyclic group that contains at least one hetero atom optionally selected from N, O, and S and may be optionally substituted.

Further, among the compounds having the Formula (I), examples of the most preferred compounds include the followings.

R' represents CF3,

Ai, A2, A3 and A4 each independently represent C-Y or N,

Bi, B2, B3 and B4 each independently represent C-X or N, X and Y each independently represent hydrogen, halogen, C alkyl or C haloalkyl, and particularly preferably hydrogen, methyl, chloro, bromo or CF3,

R ¹ represents hydrogen, or may form, together with Y of A2, C2-3 alkylene when n represents 1 and A2 represents C-Y,

R ² represents hydrogen or CM alkyl, and particularly preferably hydrogen or methyl,

R ³ represents hydrogen or CM alkyl,

R ⁴ represents hydrogen, CM alkyl-carbonyl, CM haloalkyl-carbonyl, C3-6 cycloalkyl-carbonyl, CM alkoxy-Ci-4 alkyl-carbonyl, CM thioalkoxy-Ci-4 alkyl-carbonyl, CM alkylsulfenyl-Ci-4 alkyl- carbonyl, CM alkylsulfonyl-Ci-4 alkyl-carbonyl or CM alkylamino-carbonyl, and particularly preferably CM alkyl-carbonyl, CM haloalkyl-carbonyl or C3-6 cycloalkyl-carbonyl.

Examples of the subgroups of the compounds having the Formula (I) of the present invention w.

Wherein, X ¹ , X ² , X ³ , X ⁴ and X ⁵ have the same meanings as those defined with respect to X; Y , Y ² , Y ³ and Y ⁴ have the same meanings as those defined with respect to Y; and R ¹ , R ² , R ³ and R ⁴ have

Wherein, X ¹ , X ² , X ³ , X ⁴ and X ⁵ have the same meanings as those defined with respect to X; Y , Y ² and Y ⁴ have the same meanings as those defined with respect to Y; and m, R ² , R ³ and R ⁴ have the same meanings as those described above. (l-2-a)

Y„ R1 R2

Wherein, X ¹ , X ² , X ³ , X ⁴ and X ⁵ have the same meanings as those defined with respect to X; Y , Y ² , Y ³ and Y ⁴ have the same meanings as those defined with respect to Y; and R ¹ , R ² , R ³ and R ⁴ have

Wherein, X ¹ , X ² , X ³ , X ⁴ and X ⁵ have the same meanings as those defined with respect to X; Y , Y ² and Y ⁴ have the same meanings as those defined with respect to Y; and m, R ² , R ³ and R ⁴ have the

Wherein, X ¹ , X ² , X ³ , X ⁴ and X ⁵ have the same meanings as those defined with respect to X; Y , Y ² , Y ³ and Y ⁴ have the same meanings as those defined with respect to Y; and R ¹ , R ² , R ³ and R ⁴ have

Wherein, X ¹ , X ² , X ³ , X ⁴ and X ⁵ have the same meanings as those defined with respect to X; Y , Y ² and Y ⁴ have the same meanings as those defined with respect to Y; and m, R ² , R ³ and R ⁴ have the same meanings as those described above. The compound of Formula (Int. 1) in Preparation method (a) is obtained by hydrolysis of the compound of Formula (Int. 3), which can be produced with reference to the method described in Japanese Patent Application No. 2009-250744, in an appropriate solvent like water-containing ethanol ochloric acid:

Representative examples of the compound of Formula (Int. 3) include N- {4-[5-(3,5- dichlorophenyl)-2-oxo-5-(trifluoromethyl)-l,3- oxazolidin-3-yl]-2-(trifluoromethyl)benzyl}propane amide, N- {4-[5-(3,5-dichlorophenyl)-2-oxo-5-(trifluoromethyl)-l,3- oxazolidin-3-yl]-2-

(trifluoromethyl)benzyl}cyclopropane carboxamide, N- {4-[2-oxo-5-(3,4,5-trichlorophenyl)-5- (trifluoromethyl)-l,3- oxazolidin-3-yl]-2-(trifluoromethyl)benzyl}propane amide, N- {4-[2-oxo-5-(3,4,5- trichlorophenyl)-5-(trifluoromethyl)-l,3- oxazolidin-3-yl]-2-(trifluoromethyl)benzyl}cyclopropane carboxamide, 2-cyclopropyl-N- {4-[2-oxo-5-(3,4,5-trichlorophenyl)-5- (trifluoromethyl)-l,3-oxazolidin- 3-yl]-2-(trifluoromethyl)benzyl} acetamide, N- {4-[2-oxo-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)- 1,3- oxazolidin-3-yl]-2-(trifluoromethyl)benzyl} acetamide, 3,3,3-trifluoro-N- {4-[2-oxo-5-(3,4,5- trichlorophenyl)-5- (trifluoromethyl)-l,3-oxazolidin-3-yl]-2-(trifluoromethyl)be nzyl}propane amide, N- (l- {4-[2-oxo-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-l,3- oxazolidin-3-yl]phenyl}ethyl)propane a m i d e , N-(l S)-l- {4-[2-oxo-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-l,3- oxazolidin-3- yl]phenyl} ethyl)cyclopropane carboxamide, N-(lR)-l- {4-[2-oxo-5-(3,4,5-trichlorophenyl)-5- (trifluoromethyl)-l,3-oxazolidin-3-yl]phenyl} ethyl)cyclopropane carboxamide, N-[4- {2-oxo-5- (trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-l,3-oxazolid in-3-yl} -2-(trifluoromethyl)benzyl]propane a m i d e , N-[4- {5-[3,5-bis(trifluoromethyl)phenyl]-2-oxo-5-(trifluoromethyl )-l,3-oxazolidin-3-yl}-2- (trifluoromethyl)benzyl]propane amide, N- {5-[5-(3,5-dichlorophenyl)-2-oxo-5-(trifluoromethyl)-l,3- oxazolidin-3-yl]-2,3-dihydro-lH-inden-l-yl}propane amide, and N- {5-[2-oxo-5-(3,4,5-trichlorophenyl)- 5-(trifluoromethyl)-l,3- oxazolidin-3-yl]-2,3-dihydro-lH-inden-l -yl} cyclopropane carboxamide. The reaction of the Preparation method (a) can be carried out in a suitable diluent, and examples thereof include aliphatic hydrocarbons (e.g. hexane, cyclohexane, heptane etc.), aliphatic halogenated hydrocarbons (e.g. dichloromethane, chloroform, carbon tetrachloride, dichloroethane, etc.), aromatic hydrocarbons (e.g. benzene, toluene, xylene, chlorobenzene etc.), ethers (e.g. diethyl ether, dibutyl ether, dimethoxyethane (DME), tetrahydrofuran, dioxane etc.), esters (e.g. ethyl acetate, ethyl propionate etc.), acid amides (e.g. dimethylformamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone etc.), nitriles (e.g. acetonitrile, propionitrile etc.), dimethylsulfoxide (DMSO), water or mixed solvents thereof and the like. Examples of the base for Preparation method (a) include alkali metal bases like lithium hydride, sodium hydride, potassium hydride, butyl lithium, tert-butyl lithium, trimethylsilyl lithium, lithium hexamethyl disilazide, sodium carbonate, potassium carbonate, cesium carbonate, tripotassium phosphate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, sodium-tert- butoxide, and potassium-tert-butoxide, organic bases like triethylamine, diisopropylethylamine, tributylamine, N-methylmorpholine, N,N-dimethylaniline, Ν,Ν-diethylaniline, 4-tert-butyl-N,N- dimethylaniline, pyridine, picoline, lutidine, diazabicyclo undecene, diazabicyclo octane, and imidazole, and the like.

Preparation method (a) can be carried out within a substantially wide temperature range. It may be generally carried out at the temperature from about -78°C to about 200°C, preferably from about - 10°C to about 150°C. Said reaction is desirably carried out at normal pressure although it may be carried out under elevated or reduced pressure. The reaction time is from 0.1 to 72 hours, preferably from 0.1 to 24 hours.

For carrying out Preparation method (a), for example, by reacting from 1 to 3 mole of base and from 1 to 3 mole of the compound of Formula (Int. 2) with 1 mole of the compound of Formula (Int. 1) in a diluent, for example toluene, the compound having the Formula (I) of the present invention can be obtained.

Representative examples of the compound of Formula (Int. 1) include N-[4- {[3,3,3-trifluoro-2- hydroxy-2-(3,4,5-trichlorophenyl)propyl]amino}-2-(trifluorom ethyl)benzyl]propane amide, and N-[4- {[3,3,3-trifluoro-2-hydroxy-2-(3,4,5-trichlorophenyl)propyl] amino} -2- (trifluoromethyl)benzyl]cyclopropane carboxamide.

Representative examples of the compound of Formula (Int. 2) include formaldehyde, thionyl chloride, and sulfuryl chloride.

Preparation method (b) can be carried out with reference to the method described in Journal of Organic Chemistry, 2006, 71, 1258-1261, etc.

The compound of Formula (1-2), which is a starting material for Preparation method (b), is included in the compounds of the present invention, and representative examples thereof include N- {4- [2-oxide-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-l,2,3 -oxathiazolin-3-yl]-2-

(trifluoromethyl)benzyl}propane amide, N- {4-[2-oxide-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)- l,2,3-oxathiazolin-3-yl]-2-(trifluoromethyl)benzyl}cycloprop ane carboxamide , and N- {5-[2-oxide-5- (3 ,4,5-trichlorophenyl)-5-(trifluoromethyl)- 1 ,2,3-oxathiazolin-3-yl] -2,3-dihydro- 1 H-inden- 1 -yl)propane amide. Examples of the diluent used for Preparation method (b) include methylene chloride, chloroform, dichloroethane, and acetonitrile.

Examples of the oxidizing agent used for Preparation method (b) include sodium periodate.

Examples of the catalyst used for Preparation method (b) include ruthenium (III) chloride.

For carrying out Preparation method (b), for example, by reacting from 0.01 to 0.1 mole of catalyst, for example ruthenium (III) chloride, and from 1 to 5 mole of oxidizing agent, for example sodium periodate, with 1 mole of the compound of Formula (1-2) in a diluent, for example methylene chloride, acetonitrile, the compound having the Formula (1-3) that is included in the compounds having the Formula (I) of the present invention can be obtained.

As shown in Scheme 1 , Preparation methods (a) and (b) can be performed according to an appropriate synthetic process.

Further, as shown in Scheme 2, hydrolysis of the compound of Formula (Int. 4), which can be produced with reference to the method described in Japanese Patent Application No. 2009-250744 described above, can give the compound of Formula (Int. 5), the compound of Formula (Int. 6) can be synthesized therefrom according to Preparation method (a) and/or (b), and subsequently the compound having the Formula (1-4), (1-5) or (1-6) that is included in the compounds having the Formula (I) of the present invention can be produced by following the method described in Japanese Patent Application No. 2009-250744 described above.

(Scheme 2)

Some of the compounds having the Formula (I) of the present invention may have an asymmetric carbon, and therefore an optical isomer is included therein.

The compounds having the Formula (I) of the present invention exhibit a potent pesticidal effect, and therefore can be used as pesticides. Furthermore, the active compounds having the Formula (I) of the present invention exhibit a selective controlling effect against noxious pests without causing any damages on crop plants that are cultivated. Therefore, the compounds of the present invention can be used for controlling a wide variety of harmful organisms including, for example, harmful sucking insects, chewing insects and other plant parasitic pests, stored grain pests, hygienic pests etc., and can be applied for the removal and eradication of them.

Examples of the pests include the pests described below.

As an insect, coleopteran pests, such as Callosobruchus Chinensis, Sitophilus zeamais, Tribolium castaneum, Epil achna vigintio ctomaculata, Agriote s o gurae fus cic o llis , Anomala rufocupre a, Leptmotarsadecemlineata, Diabrotica spp., Monochamus alternatus endai, Lissorhoptrus oryzophilus, Lyctus brunneus; lepidopteran pests, such as Lymantria dispar, Malacosoma neustria, Pieris rapae crucivora, Spodoptera litura, Mamestra brassicae, Chilo suppressalis, Ostrinia nubilalis, Cadra cautella, Adoxophyes honmai, Cydia pomonella, Agrotis segetum, Galleria mellonella, Plutella xylostella, Heliothis virescens, Phyllocnistis citrella; hemipterous pests, such as Nephotettix cincticeps, Nilaparvata lugens, Pseudococcus comstocki,

Unaspis yanonensis, Myzus persicas, Aphis pomi, Aphis gossypii, Lipaphis erysimi, Stephanitis nashi, Nezara spp., Trialeurodes vaporariorum, Psylla spp.; thysanoptera pests, such as Thrips palmi, Franklinella occidentalis; orthopteran pests, such as Gryllotalpa africana, Locusta migratoria; blattaria pests, such as Blatella germanica, Periplaneta americana, Reticulitermes speratus,

Coptotermes formosanus; dipterous pests, such as Musca domestica, Aedes aegypti, Delia platura, Culex pipiens pallens, Anopheles sinensis, Culex tritaeniorhynchus, Liriomyza trifolii and the like can be mentioned.

Further, as mites, Tetranychus cinnabarinus, Tetranychus urticae, Panonychus citri, Aculops pelekassi, Tarsonemus spp. and the like can be mentioned.

In addition, as nematodes, Meloidogyne incognita, Bursaphelenchus xylophilus, Aphelenchoides besseyi, Heterodera glycines, Pratylenchus spp. and the like can be mentioned.

In veterinary medicine field, i.e., veterinary science, the active compounds of the present invention can be effectively used against various harmful animal parasites, particularly, ectoparasites or endoparasites. The term "endoparasites" include in particular worms (tapeworm, eelworm, trematode and the like) and Plasmodium (coccidium and the like). The term "ectoparasites" include in general and preferably an arthropod, in particular insects (fly (a fly which can sting and suck), larva of parasitic fly, sucking lice, crab lice, bird lice, flea, and the like) or acaroid mites (ticks and the like, for example, hard tick and soft tick) or mites (itch mite, chigger mite, bird mite and the like). These parasites are as follows: from Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; particularly, for representative examples, Linognathus setosus, Linognathus vituli, Linognathus ovillus, Linognathus oviformis, Linognathus pedalis, Linognathus stenopsis, Haematopinus asini macrocephalus, Haematopinus eurystemus, Haematopinus suis, Pediculus humanus capitis, Pediculus humanus corporis, Phylloera vastatrix, Phthirus pubis, and Solenopotes capillatus; from Mallophagida and Amblycerina and Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.; particularly, for representative examples, Bovicola bovis, Bovicola ovis, Bovicola limbata, Damalina bovis, Trichodectes canis, Felicola subrostratus, Bovicola caprae, Lepikentron ovis, and Werneckiella equi; from Diptera and Nematocerina and Brachycerina, for example, Aedes spp., Anopheles ssp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp. , Haematopota spp., Philipomyia spp, Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp., Tipula spp.; particularly, for representative examples, Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles gambiae, Anopheles maculipennis, Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Fannia canicularis, Sarcophaga carnaria, Stomoxys calcitrans, Tipula paludosa, Lucilia cuprina, Lucilia sericata, Simulium reptans, Phlebotomus papatasi, Phlebotomus longipalpis, Odagmia ornata, Wilhelmia equina, Boophthora erythrocephala, Tabanus bromius, Tabanus spodopterus, Tabanus atratus, Tabanus sudeticus, Hybomitra ciurea, Chrysops caecutiens, Chrysops relictus, Haematopota pluvialis, Haematopota italica, Musca autumnalis, Musca domestica, Haematobia irritans irritans, Haematobia irritans exigua, Haematobia stimulans, Hydrotaea irritans, Hydrotaea albipuncta, Chrysomya chloropyga, Chrysomya bezziana, Oestrus ovis, Hypoderma bovis, Hypoderma lineatum, Przhevalskiana silenus, Dermatobia hominis, Melophagus ovinus, Lipoptena capreoli, Lipoptena cervi, Hippobosca variegata, Hippobosca equina, Gasterophilus intestinalis, Gasterophilus haemorroidalis, Gasterophilus interrnis, Gasterophilus nasalis, Gasterophilus nigricornis, Gasterophilus pecorum, Braula coeca; from Siphonapterida, for example, Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp. ; particularly, for representative examples, Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, and Xenopsylla cheopis; from Heteropterida, for example, Cimex spp., Triatoma spp., Rhodnius spp., and Panstrongylus spp.; from Blattarida, for example, Blatta orientalis, Periplaneta americana, Blattela germanica, and Supella spp. (for example, Suppella longipalpa); from Acari (Acarina), Metastigmata and Mesostigmata, for example, Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Dermanyssus spp., Rhipicephalus spp. (original genus of heteroxenous mites), Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp.; particularly, for representative examples, Argas persicus, Argas reflexus, Ornithodorus moubata, Otobius megnini, Rhipicephalus (Boophilus) microplus, Rhipicephalus (Boophilus) decoloratus, Rhipicephalus (Boophilus) annulatus, Rhipicephalus (Boophilus) calceratus, Hyalomma anatolicum, Hyalomma aegypticum, Hyalomma marginatum, Hyalomma transiens, Rhipicephalus evertsi, Ixodes ricinus, Ixodes hexagonus, Ixodes canisuga, Ixodes pilosus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysalis cinnabarina, Haemaphysalis otophila, Haemaphysalis leachi, Haemaphysalis longicorni, Dermacentor marginatus, Dermacentor reticulatus, Dermacentor pictus, Dermacentor albipictus, Dermacentor andersoni, Dermacentor variabilis, Hyalomma mauritanicum, Rhipicephalus sanguineus, Rhipicephalus bursa, Rhipicephalus appendiculatus, Rhipicephalus capensis, Rhipicephalus turanicus, Rhipicephalus zambeziensis, Amblyomma americanum, Amblyomma variegatum, Amblyomma maculatum, Amblyomma hebraeum, Amblyomma cajennense, Dermanyssus gallinae, Ornithonyssus bursa, Ornithonyssus sylviarum, and Varroa jacobsconi; from Actinedida (Prostigmata) and Acaridida (Astigmata), for example, Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp, Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.; particularly, for representative examples, Cheyletiella yasguri, Cheyletiella blakei, Demodex canis, Demodex bovis, Demodex ovis, Demodex caprae, Demodex equi, Demodex caballi, Demodex suis, Neotrombicula autumnalis, Neotrombicula desaleli, Neoschonegastia xerothermobia, Trombicula akamushi, Otodectes cynotis, Notoedres cati, Sarcoptis canis, Sarcoptes bovis, Sarcoptes ovis, Sarcoptes rupicaprae (=S. caprae), Sarcoptes equi, Sarcoptes suis, Psoroptes ovis, Psoroptes cuniculi, Psoroptes equi, Chorioptes bovis, Psoergates ovis, Pneumonyssoidic mange, Pneumonyssoides caninum, and Acarapis woodi.

The active compounds of the present invention are also useful for removing an arthropod, a worm and a plasmodium which attacks an animal. Examples of the animal include an agricultural animals such as a cow, a sheep, a goat, a horse, a pig, a donkey, a camel, a buffalo, a rabbit, a chicken, a turkey, a duck, a goose, a cultured fish, a honey bee, etc. In addition, a pet which is also called as a companion animal, for example, a dog, a cat, a caged bird, an aquarium fish, and a laboratory animal (e.g., a hamster, a guinea pig, a rat, a mouse and the like) are also included.

With control of the arthropod, larvae, and/or plasmodium by using the active compound of the present invention, death ratio of a host animal can be reduced and productivity (for meat, milk, wool, leather, egg, and honey) and health of the animal can be improved. As a result, it is intended to achieve economically more favorable and simple animal breeding.

For example, it is preferable that sucking of host blood by a parasite is either prevented or inhibited (if possible). Parasite removal can be useful for preventing infection which is caused by inflammatory pathogens.

The term "removal" that is used in the present specification regarding a veterinary medicine field means that the active compounds are effective for reducing the occurrence ratio of each parasite in the animal infected with it to a harmless level. More specifically, the term "removal" that is used in the present specification means that the active compounds are effective for destroying parasites, inhibiting growth or propagation thereof.

In the present invention, substances having pesticidal effects against harmful pests encompassing all of such pests are referred to as pesticides.

When used as pesticides, the active compounds of the present invention can be prepared in the form of a common preparation. Such preparation form may include, for example, liquids, emulsions, wettable powders, granulated wettable powders, suspensions, powders, foams, pastes, tablets, granules, aerosols, natural or synthetic agents impregnated with the active compounds, microcapsules, coating agents for seeds, formulations equipped with a combustion device (the combustion device can be a smoke or fog cartridge, a can or a coil, etc.) and ULV [cold mist, warm mist], and the like.

These preparations can be produced by known methods per se. For example, they can be prepared by mixing the active compounds with extenders, namely, liquid diluents or carriers; liquefied gas diluents or carriers; solid diluents or carriers and, optionally, with surfactants, namely, emulsifiers and/or dispersants and/or foam formers and the like.

In case of using water as an extender, for example, organic solvents can be used as auxiliary solvents. Liquid diluents or carriers may include, for example, aromatic hydrocarbons (e.g. xylene, toluene, alkyl naphthalene etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (e.g. chlorobenzenes, ethylene chlorides, methylene chlorides etc.), aliphatic hydrocarbons (e.g. cyclohexanes or paraffins (e.g. mineral oil fractions)), alcohols (e.g. butanol, glycol and ethers or esters thereof, etc.), ketones (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone etc.), strong polar solvents (e.g. dimethyl formamide, dimethyl sulfoxide etc.), water and the like. Liquefied gas diluent or carrier may include those presented as gas at atmospheric pressure and temperature, for example, bulan, propane, nitrogen gas, carbon dioxide, and aerosol propellant such as halogenated hydrocarbons.

Examples of the solid diluents may include ground natural minerals (for example, kaolins, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, etc.) and ground synthetic minerals (for example, highly dispersed silicic acid, alumina and silicate, etc.) and the like.

Examples of the solid carriers for granules may include crushed and fractionated rocks (for example, calcite, marble, pumice, sepiolite and dolomite, etc.), synthetic granules of inorganic or organic powders, and fine granules of organic materials (for example, sawdust, coconut shells, maize cobs and tobacco stalks, etc.) and the like.

Examples of the emulsifiers and/or foam formers may include nonionic and anionic emulsifiers [for example, polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (for example, alkylaryl polyglycol ether), alkyl sulfonates, alkyl sulfates and aryl sulfonates] and albumin hydrolyzates and the like. The dispersants include lignin sulfite waste liquid and methyl cellulose.

Binders may also be used in the preparations (powders, granules and emulsion). Examples of the binders may include carboxymethyl cellulose, and natural or synthetic polymers (for example, gum Arabic, polyvinyl alcohol and polyvinyl acetate, etc).

Colorants may also be used. Examples of the colorants may include inorganic pigments (for example, iron oxide, titanium oxide and Prussian blue, etc.), organic dyes such as Alizarin dyes, azo dyes or metal phthalocyanine dyes, and further, trace elements such as salts of iron, manganese, boron, copper, cobalt, molybdenum or zinc.

The preparation may generally include the above active components in an amount from 0.1 to 95% by weight, preferably from 0.5 to 90% by weight. The active compounds of the Formula (I) of the present invention can be provided as mixtures with other active compounds such as pesticides, poison baits, sterilizing agents, acaricidal agents, nematocides, fungicides, growth regulating agents, herbicides, and the like in the form of commercially useful preparation or a usage form prepared from such preparation. The pesticides may include, for example, organic phosphorous agents, carbamate agents, carboxylate agents, chlorinated hydrocarbon agents, neonicotinoid pesticides, and pesticidal substances produced by microorganisms, etc. Further, the active compounds of the Formula (I) of the present invention can be provided as mixtures with synergists. Such preparation and usage form may include those that are commercially useful. The synergists are not necessarily active by themselves. Rather, they are the compounds which enhance the activity of the active compounds. The amount of the active compounds of the Formula (I) of the present invention in a commercially useful form may vary over a broad range.

The concentration of the active compounds of the Formula (I) of the present invention for actual use can be, for example, in the range from 0.0000001 to 95% by weight, preferably from 0.00001 to 90% by weight. The compounds of the Formula (I) of the present invention can be used according to any common methods that are appropriate for a usage form.

The active compounds of the present invention have stability that is effective for alkaline substances present in lime materials when the compounds are used against hygienic pests and storage pests. In addition, they exhibit excellent residual effectiveness in woods and soils. Generally, when the active compounds of the present invention are used for the treatment of animals, they can be directly applied to the animal. Preferably, the compounds are applied in the form of pharmaceutical composition which may include a vehicle, an auxiliary agent, or both, that are known in the art and pharmaceutically acceptable.

For a veterinary medicine field and animal breeding, the active compounds can be applied (administered) according to various known ways, for example; intraintestinal administration with a tablet, a capsule, a drink, a drinkable medicine, granules, paste, and bolus administration, feed-through method, suppository; non-intraintestinal administration based on skin application such as injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), embedding, intranasal application, bathing or immersion, spray, pouring, dropping, washing and scattering, and by using a molding article containing the active compounds such as a necklace, an earmark, a tag, a leg brace, a halter, a marking device and the like. The active compounds of the present invention can be formulated into an appropriate formulation form that can be applied with a shampoo, aerosol, a non-pressurized spray, for example, a pump spray and a vaporizer spray, etc.

When used for livestock, fouls, pets and the like, the active compounds of the present invention can be used as a formulation which includes them in an amount from 1 to 80%> by weight (for example, powders, wettable powders (WP), emulsion, emulsifiable concentrate (EC), fluid, homogeneous solution and suspension concentrate (SC)), and the formulation can be applied as it is or after dilution (for example, dilution of 100 to 10,000 times), or as a chemical bath as an alternative method.

When used in a veterinary medicine field, the active compounds of the present invention can be used in combination with appropriate synergistic agents or other active compounds, for example, acaricides, insecticides, parasticides, anti-plasmodium agents, etc.

The active compounds of the present invention have low toxicity, and therefore can be safely used for warm-blooded animals.

[EXAMPLES]

Hereinbelow, the present invention is described in greater detail with reference to the following examples. However, the present invention is not limited thereto.

Synthetic example 1

S ynth e s i s o f N- {4-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-l,3- oxazolidin-3-yl]-2-

N- {4-[2-oxo-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-l,3- oxazolidin-3-yl]-2-(trifluoro- methyl)benzyl}propane amide (542 mg) was added to a solution of 1,4-dioxane (10 mL), water (10 mL) and potassium hydroxide (108 mg), and stirred at 70°C for 1 hour. After the reaction, 1,4-dioxane was distilled off under reduced pressure, and cone, hydrochloric acid (70 mg) was added and stirred under ice cooling. The resultant was extracted with ethyl acetate, washed with water and saturated brine, and the organic layer is dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residues were purified by silica-gel column chromatography to give N-[4- {[3,3,3-trifluoro-2-hydroxy- 2-(3,4,5-trichlorophenyl)propyl]amino} -2-(trifluoromethyl)benzyl]propane amide (503 mg).

1H-NMR (CDC13) 5:1.14 (3H, t), 2.21 (2H, q), 3.63-3.66 (1H, m), 3.88-3.93 (1H, m), 3.98-4.00 (1H, m), 4.40-4.43 (3H, m), 5.74 (1H, br s), 6.70-6.71 (1H, m), 6.86 (1H, s), 7.27-7.30 (1H, m), 7.64 (2H, s)

Step 2

Synthesis of N- {4-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-l,3- oxazolidin-3-yl]-2- (trifluoromethyl)benzyl}propane amide

N-[4- {[3,3,3-Trifluoro-2-hydroxy-2-(3,4,5-trichlorophenyl) propyl] amino} -2-

(trifluoromethyl)benzyl]propane amide (250 mg) and formaldehyde (70 mg) were added to toluene (20 mL), and stirred at 90°C for 5 hours. After the reaction, the solvent was distilled off under reduced pressure and the residues were purified by silica-gel column chromatography to give N- {4-[5- (3,4,5- trichlorophenyl)-5-(trifluoromethyl)-l ,3-oxazolidin-3-yl]-2-(trifluoromethyl)benzyl}propane amide (100 mg).

1H-NMR (CDC13) 8: 1.13-1.16 (3H, m), 2.18-2.23 (3H, m), 3.77-3.81 (1 H, m), 4.12-4.15 (1H, m), 4.50(2H, d), 5.20 (2H, d), 5.73 (1H, br s), 6.67 (1H, d), 6.77 (1H, d), 7.48 (1H, d), 7.59 (2H, s)

Synthetic example 2 Synthesis of N- {4-[2-oxide-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-l, 2,3-oxathiazolin-3- -2-(trifluoromethyl)benzyl}propane amide (No. 3-17)

N-[4- {[3,3,3-Trifluoro-2-hydroxy-2-(3,4,5-trichlorophenyl)propyl] amino} -2-(trifluoro- methyl)benzyl]propane amide (160 mg), triethylamine (130 mg), and N,N-dimethyl-4-aminopyridine (4 mg) were added to dichloromethane (10 niL), and under ice cooling, added dropwise with thionyl chloride (57 mg). After the dropwise addition, the mixture was stirred for 2.5 hours at room temperature. After the reaction, the solvent was distilled off under reduced pressure and the residues were purified by silica-gel column chromatography to give N- {4-[2-oxide-5-(3,4,5-trichlorophenyl)-5- (trifluoromethyl)-l,2,3-oxathiazolin-3-yl]-2-(trifluoromethy l)benzyl}propane amide (157 mg).

1H-NMR (CDC13) δ: 1H-NMR (CDC13) 8: 1.14-1.16 (3H, m), 2.17-2.27 (2H, m), 4.09-4.74 (4H, m), 5.80 (1H, br s), 7.22-7.65 (5H, m)

Synthetic example 3

Synthesis of N- {4-[2,2-dioxide-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl )-l,2,3-oxathiazolin- -yl]-2-(trifluoromethyl)benzyl}propane amide (No. 5-17)

N- {4-[2-Oxide-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-l, 2,3-oxathiazolin-3-yl]-2-(tri- fluoromethyl)benzyl} propane amide (190 mg) was dissolved in dichloromethane ( 1.5 mL) and acetonitrile (1.5 mL). Under ice cooling, ruthenium (III) chloride (5 mg) was added and stirred for 10 minutes. Subsequently, sodium periodate (111 mg) and phosphate buffer solution (pH 7, 1.5 mL) were added thereto and stirred for 2 hours under ice cooling. Temperature was raised to room temperature and the mixture was filtered using Celite. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residues were purified by silica-gel column chromatography to give N- {4-[2,2-dioxide-5-(3,4,5-trichlorophenyl)- 5-(trifluoromethyl)- l,2,3-oxathiazolin-3-yl]-2-(trifluoromethyl)benzyl}propane amide (157 mg).

1H-NMR (CDC13) δ:7.68-7.47 (4H, m), 7.29 (1H, m), 5.87 (1H, m), 4.67-4.23 (4H, m), 2.28-2.18 (2H, m), 1.18-1.11 (3H, t) Compounds having the Formula (I) of the present invention and novel intermediates that are obtained according to the methods similar to the Synthetic example above or the methods described in detail above are described in Tables 1 to 6 and Tables 7 to 1 1, respectively. Their NMR measurement data are described in the NMR table. Further, each compound obtained from the Synthetic examples above is also described in the corresponding table.

Abbreviated symbols in the tables are as follows.

Me: methyl, Et: ethyl, Pr: propyl, Bu: butyl, n-: normal, cyclo-: cyclo, tert-: tertiary.

Further, the compound given with "-a" in compound number indicates S form for the stereo h R ¹ and R ² are bound, "-b" indicates R form.

Wherein, X ¹ , X ⁵ , Y ¹ , Y ² , Y ⁴ , R ² and R ³ represent hydrogen.

Table 1

Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

1-1 CI H CI CF ₃ H H

1-2 CI H CI CF ₃ H MeCO

1-3 CI H CI CF ₃ H EtCO

1-4 CI H CI CF ₃ H n-PrCO

1-5 CI H CI CF ₃ H cyclo-PrCO

1-6 CI H CI CF ₃ H cyclo-PrCH ₂ CO

1-7 CI H CI CF ₃ H CF ₃ CH ₂ CO

1-8 CI H CI CF ₃ H CH ₃ SCH ₂ CO

1-9 CI H CI CF ₃ H CH ₃ SOCH ₂ CO

1-10 CI H CI CF ₃ H CH ₃ S0 ₂ CH ₂ CO

1-11 CI H CI CF ₃ H CH ₃ OCH ₂ CH ₂ CO

1-12 CI H CI CF ₃ H CH ₃ OCH(Me)CH ₂ CO

1-13 CI H CI CF ₃ H EtNHCO

1-14 CI H CI CF ₃ H tert-BuOC(=0)

1-15 CI CI CI CF ₃ H H

1-16 CI CI CI CF ₃ H MeCO

1-17 CI CI CI CF ₃ H EtCO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

1-18 CI CI CI CF ₃ H n-PrCO

1-19 CI CI CI CF ₃ H cyclo-PrCO

1-20 CI CI CI CF ₃ H cyclo-PrCH ₂ CO

1-21 CI CI CI CF ₃ H CF ₃ CH ₂ CO

1-22 CI CI CI CF ₃ H CH ₃ SCH ₂ CO

1-23 CI CI CI CF ₃ H CH ₃ SOCH ₂ CO

1-24 CI CI CI CF ₃ H CH ₃ S0 ₂ CH ₂ CO

1-25 CI CI CI CF ₃ H CH ₃ OCH ₂ CH ₂ CO

1-26 CI CI CI CF ₃ H CH ₃ OCH(Me)CH ₂ CO

1-27 CI CI CI CF ₃ H EtNHCO

1-28 CI CI CI CF ₃ H tert-BuOC(=0)

1-29 CI CI CI CI H H

1-30 CI CI CI CI H MeCO

1-31 CI CI CI CI H EtCO

1-32 CI CI CI CI H n-PrCO

1-33 CI CI CI CI H cyclo-PrCO

1-34 CI CI CI CI H cyclo-PrCH ₂ CO

1-35 CI CI CI CI H CF ₃ CH ₂ CO

1-36 CI CI CI CI H CH ₃ SCH ₂ CO

1-37 CI CI CI CI H CH ₃ SOCH ₂ CO

1-38 CI CI CI CI H CH ₃ S0 ₂ CH ₂ CO

1-39 CI CI CI CI H CH ₃ OCH ₂ CH ₂ CO

1-40 CI CI CI CI H CH ₃ OCH(Me)CH ₂ CO

1-41 CI CI CI CI H EtNHCO

1-42 CI CI CI CI H tert-BuOC(=0)

1-43 CI CI CI Me H H

1-44 CI CI CI Me H MeCO

1-45 CI CI CI Me H EtCO

1-46 CI CI CI Me H n-PrCO

1-47 CI CI CI Me H cyclo-PrCO

1-48 CI CI CI Me H cyclo-PrCH ₂ CO

1-49 CI CI CI Me H CF ₃ CH ₂ CO

1-50 CI CI CI Me H CH ₃ SCH ₂ CO

1-51 CI CI CI Me H CH ₃ SOCH ₂ CO

1-52 CI CI CI Me H CH ₃ S0 ₂ CH ₂ CO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

1-53 CI CI CI Me H CH ₃ OCH ₂ CH ₂ CO

1-54 CI CI CI Me H CH ₃ OCH(Me)CH ₂ CO

1-55 CI CI CI Me H EtNHCO

1-56 CI CI CI Me H tert-BuOC(=0)

1-57 CI CI CI H H H

1-58 CI CI CI H H MeCO

1-59 CI CI CI H H EtCO

1-60 CI CI CI H H n-PrCO

1-61 CI CI CI H H cyclo-PrCO

1-62 CI CI CI H H cyclo-PrCH ₂ CO

1-63 CI CI CI H H CF ₃ CH ₂ CO

1-64 CI CI CI H H CH ₃ SCH ₂ CO

1-65 CI CI CI H H CH ₃ SOCH ₂ CO

1-66 CI CI CI H H CH ₃ S0 ₂ CH ₂ CO

1-67 CI CI CI H H CH ₃ OCH ₂ CH ₂ CO

1-68 CI CI CI H H CH ₃ OCH(Me)CH ₂ CO

1-69 CI CI CI H H EtNHCO

1-70 CI CI CI H H tert-BuOC(=0)

1-71 CF ₃ H H CF ₃ H H

1-72 CF ₃ H H CF ₃ H MeCO

1-73 CF ₃ H H CF ₃ H EtCO

1-74 CF ₃ H H CF ₃ H n-PrCO

1-75 CF ₃ H H CF ₃ H cyclo-PrCO

1-76 CF ₃ H H CF ₃ H cyclo-PrCH ₂ CO

1-77 CF ₃ H H CF ₃ H CF ₃ CH ₂ CO

1-78 CF ₃ H H CF ₃ H CH ₃ SCH ₂ CO

1-79 CF ₃ H H CF ₃ H CH ₃ SOCH ₂ CO

1-80 CF ₃ H H CF ₃ H CH ₃ S0 ₂ CH ₂ CO

1-81 CF ₃ H H CF ₃ H CH ₃ OCH ₂ CH ₂ CO

1-82 CF ₃ H H CF ₃ H CH ₃ OCH(Me)CH ₂ CO

1-83 CF ₃ H H CF ₃ H EtNHCO

1-84 CF ₃ H H CF ₃ H tert-BuOC(=0)

1-85 CF ₃ H H CI H H

1-86 CF ₃ H H CI H MeCO

1-87 CF ₃ H H CI H EtCO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

1-88 CF ₃ H H CI H n-PrCO

1-89 CF ₃ H H CI H cyclo-PrCO

1-90 CF ₃ H H CI H cyclo-PrCH ₂ CO

1-91 CF ₃ H H CI H CF ₃ CH ₂ CO

1-92 CF ₃ H H CI H CH ₃ SCH ₂ CO

1-93 CF ₃ H H CI H CH ₃ SOCH ₂ CO

1-94 CF ₃ H H CI H CH ₃ S0 ₂ CH ₂ CO

1-95 CF ₃ H H CI H CH ₃ OCH ₂ CH ₂ CO

1-96 CF ₃ H H CI H CH ₃ OCH(Me)CH ₂ CO

1-97 CF ₃ H H CI H EtNHCO

1-98 CF ₃ H H CI H tert-BuOC(=0)

1-99 CF ₃ H H Me H H

1-100 CF ₃ H H Me H MeCO

1-101 CF ₃ H H Me H EtCO

1-102 CF ₃ H H Me H n-PrCO

1-103 CF ₃ H H Me H cyclo-PrCO

1-104 CF ₃ H H Me H cyclo-PrCH ₂ CO

1-105 CF ₃ H H Me H CF ₃ CH ₂ CO

1-106 CF ₃ H H Me H CH ₃ SCH ₂ CO

1-107 CF ₃ H H Me H CH ₃ SOCH ₂ CO

1-108 CF ₃ H H Me H CH ₃ S0 ₂ CH ₂ CO

1-109 CF ₃ H H Me H CH ₃ OCH ₂ CH ₂ CO

1-110 CF ₃ H H Me H CH ₃ OCH(Me)CH ₂ CO

1-111 CF ₃ H H Me H EtNHCO

1-112 CF ₃ H H Me H tert-BuOC(=0)

1-113 CF ₃ H H H H H

1-114 CF ₃ H H H H MeCO

1-115 CF ₃ H H H H EtCO

1-116 CF ₃ H H H H n-PrCO

1-117 CF ₃ H H H H cyclo-PrCO

1-118 CF ₃ H H H H cyclo-PrCH ₂ CO

1-119 CF ₃ H H H H CF ₃ CH ₂ CO

1-120 CF ₃ H H H H CH ₃ SCH ₂ CO

1-121 CF ₃ H H H H CH ₃ SOCH ₂ CO

1-122 CF ₃ H H H H CH ₃ S0 ₂ CH ₂ CO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

1-123 CF ₃ H H H H CH ₃ OCH ₂ CH ₂ CO

1-124 CF ₃ H H H H CH ₃ OCH(Me)CH ₂ CO

1-125 CF ₃ H H H H EtNHCO

1-126 CF ₃ H H H H tert-BuOC(=0)

1-127 CF ₃ H CF ₃ CF ₃ H H

1-128 CF ₃ H CF ₃ CF ₃ H MeCO

1-129 CF ₃ H CF ₃ CF ₃ H EtCO

1-130 CF ₃ H CF ₃ CF ₃ H n-PrCO

1-131 CF ₃ H CF ₃ CF ₃ H cyclo-PrCO

1-132 CF ₃ H CF ₃ CF ₃ H cyclo-PrCH ₂ CO

1-133 CF ₃ H CF ₃ CF ₃ H CF ₃ CH ₂ CO

1-134 CF ₃ H CF ₃ CF ₃ H CH ₃ SCH ₂ CO

1-135 CF ₃ H CF ₃ CF ₃ H CH ₃ SOCH ₂ CO

1-136 CF ₃ H CF ₃ CF ₃ H CH ₃ S0 ₂ CH ₂ CO

1-137 CF ₃ H CF ₃ CF ₃ H CH ₃ OCH ₂ CH ₂ CO

1-138 CF ₃ H CF ₃ CF ₃ H CH ₃ OCH(Me)CH ₂ CO

1-139 CF ₃ H CF ₃ CF ₃ H EtNHCO

1-140 CF ₃ H CF ₃ CF ₃ H tert-BuOC(=0)

1-141 CF ₃ H CF ₃ CI H H

1-142 CF ₃ H CF ₃ CI H MeCO

1-143 CF ₃ H CF ₃ CI H EtCO

1-144 CF ₃ H CF ₃ CI H n-PrCO

1-145 CF ₃ H CF ₃ CI H cyclo-PrCO

1-146 CF ₃ H CF ₃ CI H cyclo-PrCH ₂ CO

1-147 CF ₃ H CF ₃ CI H CF ₃ CH ₂ CO

1-148 CF ₃ H CF ₃ CI H CH ₃ SCH ₂ CO

1-149 CF ₃ H CF ₃ CI H CH ₃ SOCH ₂ CO

1-150 CF ₃ H CF ₃ CI H CH ₃ S0 ₂ CH ₂ CO

1-151 CF ₃ H CF ₃ CI H CH ₃ OCH ₂ CH ₂ CO

1-152 CF ₃ H CF ₃ CI H CH ₃ OCH(Me)CH ₂ CO

1-153 CF ₃ H CF ₃ CI H EtNHCO

1-154 CF ₃ H CF ₃ CI H tert-BuOC(=0)

1-155 CF ₃ H CF ₃ Me H H

1-156 CF ₃ H CF ₃ Me H MeCO

1-157 CF ₃ H CF ₃ Me H EtCO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

1-158 CF ₃ H CF ₃ Me H n-PrCO

1-159 CF ₃ H CF ₃ Me H cyclo-PrCO

1-160 CF ₃ H CF ₃ Me H cyclo-PrCH ₂ CO

1-161 CF ₃ H CF ₃ Me H CF ₃ CH ₂ CO

1-162 CF ₃ H CF ₃ Me H CH ₃ SCH ₂ CO

1-163 CF ₃ H CF ₃ Me H CH ₃ SOCH ₂ CO

1-164 CF ₃ H CF ₃ Me H CH ₃ S0 ₂ CH ₂ CO

1-165 CF ₃ H CF ₃ Me H CH ₃ OCH ₂ CH ₂ CO

1-166 CF ₃ H CF ₃ Me H CH ₃ OCH(Me)CH ₂ CO

1-167 CF ₃ H CF ₃ Me H EtNHCO

1-168 CF ₃ H CF ₃ Me H tert-BuOC(=0)

1-169 CF ₃ H CF ₃ H H H

1-170 CF ₃ H CF ₃ H H MeCO

1-171 CF ₃ H CF ₃ H H EtCO

1-172 CF ₃ H CF ₃ H H n-PrCO

1-173 CF ₃ H CF ₃ H H cyclo-PrCO

1-174 CF ₃ H CF ₃ H H cyclo-PrCH ₂ CO

1-175 CF ₃ H CF ₃ H H CF ₃ CH ₂ CO

1-176 CF ₃ H CF ₃ H H CH ₃ SCH ₂ CO

1-177 CF ₃ H CF ₃ H H CH ₃ SOCH ₂ CO

1-178 CF ₃ H CF ₃ H H CH ₃ S0 ₂ CH ₂ CO

1-179 CF ₃ H CF ₃ H H CH ₃ OCH ₂ CH ₂ CO

1-180 CF ₃ H CF ₃ H H CH ₃ OCH(Me)CH ₂ CO

1-181 CF ₃ H CF ₃ H H EtNHCO

1-182 CF ₃ H CF ₃ H H tert-BuOC(=0)

1-183 CI CI CF ₃ CF ₃ H H

1-184 CI CI CF ₃ CF ₃ H MeCO

1-185 CI CI CF ₃ CF ₃ H EtCO

1-186 CI CI CF ₃ CF ₃ H cyclo-PrCO

1-187 CI CI CF ₃ CF ₃ H CH ₃ SCH ₂ CO

1-188 CI CI CF ₃ CF ₃ H CF ₃ CH ₂ CO

1-189 CI CI CF ₃ CF ₃ H EtNHCO

1-190 CI CI CF ₃ CF ₃ H tert-BuOC(=0)

1-191 CI H CF ₃ CF ₃ H H

1-192 CI H CF ₃ CF ₃ H MeCO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

1-193 CI H CF ₃ CF ₃ H EtCO

1-194 CI H CF ₃ CF ₃ H cyclo-PrCO

1-195 CI H CF ₃ CF ₃ H CH ₃ SCH ₂ CO

1-196 CI H CF ₃ CF ₃ H CF ₃ CH ₂ CO

1-197 CI H CF ₃ CF ₃ H EtNHCO

1-198 CI H CF ₃ CF ₃ H tert-BuOC(=0)

1-199 F H CF ₃ CF ₃ H H

1-200 F H CF ₃ CF ₃ H MeCO

1-201 F H CF ₃ CF ₃ H EtCO

1-202 F H CF ₃ CF ₃ H cyclo-PrCO

1-203 F H CF ₃ CF ₃ H CH ₃ SCH ₂ CO

1-204 F H CF ₃ CF ₃ H CF ₃ CH ₂ CO

1-205 F H CF ₃ CF ₃ H EtNHCO

1-206 F H CF ₃ CF ₃ H tert-BuOC(=0)

1-207 H F CF ₃ CF ₃ H H

1-208 H F CF ₃ CF ₃ H MeCO

1-209 H F CF ₃ CF ₃ H EtCO

1-210 H F CF ₃ CF ₃ H cyclo-PrCO

1-211 H F CF ₃ CF ₃ H CH ₃ SCH ₂ CO

1-212 H F CF ₃ CF ₃ H CF ₃ CH ₂ CO

1-213 H F CF ₃ CF ₃ H EtNHCO

1-214 H F CF ₃ CF ₃ H tert-BuOC(=0)

1-215 CI H CI Br H H

1-216 CI H CI Br H MeCO

1-217 CI H CI Br H EtCO

1-218 CI H CI Br H n-PrCO

1-219 CI H CI Br H cyclo-PrCO

1-220 CI H CI Br H cyclo-PrCH ₂ CO

1-221 CI H CI Br H CF ₃ CH ₂ CO

1-222 CI H CI Br H CH ₃ SCH ₂ CO

1-223 CI H CI Br H CH ₃ SOCH ₂ CO

1-224 CI H CI Br H CH ₃ S0 ₂ CH ₂ CO

1-225 CI H CI Br H CH ₃ OCH ₂ CH ₂ CO

1-226 CI H CI Br H CH ₃ OCH(Me)CH ₂ CO

1-227 CI H CI Br H EtNHCO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

1-228 CI H CI Br H tert-BuOC(=0)

1-229 CI CI CI Br H H

1-230 CI CI CI Br H MeCO

1-231 CI CI CI Br H EtCO

1-232 CI CI CI Br H n-PrCO

1-233 CI CI CI Br H cyclo-PrCO

1-234 CI CI CI Br H cyclo-PrCH ₂ CO

1-235 CI CI CI Br H CF ₃ CH ₂ CO

1-236 CI CI CI Br H CH ₃ SCH ₂ CO

1-237 CI CI CI Br H CH ₃ SOCH ₂ CO

1-238 CI CI CI Br H CH ₃ S0 ₂ CH ₂ CO

1-239 CI CI CI Br H CH ₃ OCH ₂ CH ₂ CO

1-240 CI CI CI Br H CH ₃ OCH(Me)CH ₂ CO

1-241 CI CI CI Br H EtNHCO

1-242 CI CI CI Br H tert-BuOC(=0)

1-243 CF ₃ H H Br H H

1-244 CF ₃ H H Br H MeCO

1-245 CF ₃ H H Br H EtCO

1-246 CF ₃ H H Br H n-PrCO

1-247 CF ₃ H H Br H cyclo-PrCO

1-248 CF ₃ H H Br H cyclo-PrCH ₂ CO

1-249 CF ₃ H H Br H CF ₃ CH ₂ CO

1-250 CF ₃ H H Br H CH ₃ SCH ₂ CO

1-251 CF ₃ H H Br H CH ₃ SOCH ₂ CO

1-252 CF ₃ H H Br H CH ₃ S0 ₂ CH ₂ CO

1-253 CF ₃ H H Br H CH ₃ OCH ₂ CH ₂ CO

1-254 CF ₃ H H Br H CH ₃ OCH(Me)CH ₂ CO

1-255 CF ₃ H H Br H EtNHCO

1-256 CF ₃ H H Br H tert-BuOC(=0)

1-257 CF ₃ H CF ₃ Br H H

1-258 CF ₃ H CF ₃ Br H MeCO

1-259 CF ₃ H CF ₃ Br H EtCO

1-260 CF ₃ H CF ₃ Br H n-PrCO

1-261 CF ₃ H CF ₃ Br H cyclo-PrCO

1-262 CF ₃ H CF ₃ Br H cyclo-PrCH ₂ CO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

1-263 CF ₃ H CF ₃ Br H CF ₃ CH ₂ CO

1-264 CF ₃ H CF ₃ Br H CH ₃ SCH ₂ CO

1-265 CF ₃ H CF ₃ Br H CH ₃ SOCH ₂ CO

1-266 CF ₃ H CF ₃ Br H CH ₃ S0 ₂ CH ₂ CO

1-267 CF ₃ H CF ₃ Br H CH ₃ OCH ₂ CH ₂ CO

1-268 CF ₃ H CF ₃ Br H CH ₃ OCH(Me)CH ₂ CO

1-269 CF ₃ H CF ₃ Br H EtNHCO

1-270 CF ₃ H CF ₃ Br H tert-BuOC(=0)

1-271 Br H Br CF ₃ H H

1-272 Br H Br CF ₃ H MeCO

1-273 Br H Br CF ₃ H EtCO

1-274 Br H Br CF ₃ H n-PrCO

1-275 Br H Br CF ₃ H cyclo-PrCO

1-276 Br H Br CF ₃ H cyclo-PrCH ₂ CO

1-277 Br H Br CF ₃ H CF ₃ CH ₂ CO

1-278 Br H Br CF ₃ H CH ₃ SCH ₂ CO

1-279 Br H Br CF ₃ H CH ₃ SOCH ₂ CO

1-280 Br H Br CF ₃ H CH ₃ S0 ₂ CH ₂ CO

1-281 Br H Br CF ₃ H CH ₃ OCH ₂ CH ₂ CO

1-282 Br H Br CF ₃ H CH ₃ OCH(Me)CH ₂ CO

1-283 Br H Br CF ₃ H EtNHCO

1-284 Br H Br CF ₃ H tert-BuOC(=0)

1-285 Br H Br CI H H

1-286 Br H Br CI H MeCO

1-287 Br H Br CI H EtCO

1-288 Br H Br CI H n-PrCO

1-289 Br H Br CI H cyclo-PrCO

1-290 Br H Br CI H cyclo-PrCH ₂ CO

1-291 Br H Br CI H CF ₃ CH ₂ CO

1-292 Br H Br CI H CH ₃ SCH ₂ CO

1-293 Br H Br CI H CH ₃ SOCH ₂ CO

1-294 Br H Br CI H CH ₃ S0 ₂ CH ₂ CO

1-295 Br H Br CI H CH ₃ OCH ₂ CH ₂ CO

1-296 Br H Br CI H CH ₃ OCH(Me)CH ₂ CO

1-297 Br H Br CI H EtNHCO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

1-298 Br H Br CI H tert-BuOC(=0)

1-299 Br H Br Br H H

1-300 Br H Br Br H MeCO

1-301 Br H Br Br H EtCO

1-302 Br H Br Br H n-PrCO

1-303 Br H Br Br H cyclo-PrCO

1-304 Br H Br Br H cyclo-PrCH ₂ CO

1-305 Br H Br Br H CF3CH2CO

1-306 Br H Br Br H CH3SCH2CO

1-307 Br H Br Br H CH3SOCH2CO

1-308 Br H Br Br H CH3SO2CH2CO

1-309 Br H Br Br H CH3OCH2CH2CO

1-310 Br H Br Br H CH ₃ OCH(Me)CH ₂ CO

1-311 Br H Br Br H EtNHCO

1-312 Br H Br Br H tert-BuOC(=0)

1-313 Br H Br Me H H

1-314 Br H Br Me H MeCO

1-315 Br H Br Me H EtCO

1-316 Br H Br Me H n-PrCO

1-317 Br H Br Me H cyclo-PrCO

1-318 Br H Br Me H cyclo-PrCH ₂ CO

1-319 Br H Br Me H CF3CH2CO

1-320 Br H Br Me H CH3SCH2CO

1-321 Br H Br Me H CH3SOCH2CO

1-322 Br H Br Me H CH3SO2CH2CO

1-323 Br H Br Me H CH3OCH2CH2CO

1-324 Br H Br Me H CH ₃ OCH(Me)CH ₂ CO

1-325 Br H Br Me H EtNHCO

1-326 Br H Br Me H tert-BuOC(=0)

1-327 Br H Br H H H

1-328 Br H Br H H MeCO

1-329 Br H Br H H EtCO

1-330 Br H Br H H n-PrCO

1-331 Br H Br H H cyclo-PrCO

1-332 Br H Br H H cyclo-PrCH ₂ CO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

1-367 Br H Br H Me EtNHCO

1-368 Br H Br H Me tert-BuOC(=0)

1-369 CI CI CI H Me H

1-370 CI CI CI H Me MeCO

1-370-a CI CI CI H Me MeCO

1-371 CI CI CI H Me EtCO

1-371-a CI CI CI H Me EtCO

1-371-b CI CI CI H Me EtCO

1-372 CI CI CI H Me n-PrCO

1-373 CI CI CI H Me cyclo-PrCO

1-373-a CI CI CI H Me cyclo-PrCO

1-374 CI CI CI H Me cyclo-PrCH ₂ CO

1-374-a CI CI CI H Me cyclo-PrCH ₂ CO

1-375 CI CI CI H Me CF ₃ CH ₂ CO

1-375-a CI CI CI H Me CF ₃ CH ₂ CO

1-376 CI CI CI H Me CH ₃ SCH ₂ CO

1-377 CI CI CI H Me CH ₃ SOCH ₂ CO

1-378 CI CI CI H Me CH ₃ S0 ₂ CH ₂ CO

1-379 CI CI CI H Me CH ₃ OCH ₂ CH ₂ CO

1-379-a CI CI CI H Me CH ₃ OCH ₂ CH ₂ CO

1-380 CI CI CI H Me CH ₃ OCH(Me)CH ₂ CO

1-381 CI CI CI H Me EtNHCO

1-382 CI CI CI H Me tert-BuOC(=0)

1-383 CF ₃ H H H Me H

1-384 CF ₃ H H H Me MeCO

1-385 CF ₃ H H H Me EtCO

1-386 CF ₃ H H H Me n-PrCO

1-387 CF ₃ H H H Me cyclo-PrCO

1-388 CF ₃ H H H Me cyclo-PrCH ₂ CO

1-389 CF ₃ H H H Me CF ₃ CH ₂ CO

1-390 CF ₃ H H H Me CH ₃ SCH ₂ CO

1-391 CF ₃ H H H Me CH ₃ SOCH ₂ CO

1-392 CF ₃ H H H Me CH ₃ S0 ₂ CH ₂ CO

1-393 CF ₃ H H H Me CH ₃ OCH ₂ CH ₂ CO

1-394 CF ₃ H H H Me CH ₃ OCH(Me)CH ₂ CO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

1-395 CF ₃ H H H Me EtNHCO

1-396 CF ₃ H H H Me tert-BuOC(=0)

1-397 CF ₃ H CF ₃ H Me H

1-398 CF ₃ H CF ₃ H Me MeCO

1-398-a CF ₃ H CF ₃ H Me MeCO

1-399 CF ₃ H CF ₃ H Me EtCO

1-399-a CF ₃ H CF ₃ H Me EtCO

1-399-b CF ₃ H CF ₃ H Me EtCO

1-400 CF ₃ H CF ₃ H Me n-PrCO

1-401 CF ₃ H CF ₃ H Me cyclo-PrCO

1-401-a CF ₃ H CF ₃ H Me cyclo-PrCO

1-402 CF ₃ H CF ₃ H Me cyclo-PrCH ₂ CO

1-402-a CF ₃ H CF ₃ H Me cyclo-PrCH ₂ CO

1-403 CF ₃ H CF ₃ H Me CF ₃ CH ₂ CO

1-403-a CF ₃ H CF ₃ H Me CF ₃ CH ₂ CO

1-404 CF ₃ H CF ₃ H Me CH ₃ SCH ₂ CO

1-405 CF ₃ H CF ₃ H Me CH ₃ SOCH ₂ CO

1-406 CF ₃ H CF ₃ H Me CH ₃ S0 ₂ CH ₂ CO

1-407 CF ₃ H CF ₃ H Me CH ₃ OCH ₂ CH ₂ CO

1-407-a CF ₃ H CF ₃ H Me CH ₃ OCH ₂ CH ₂ CO

1-408 CF ₃ H CF ₃ H Me CH ₃ OCH(Me)CH ₂ CO

1-409 CF ₃ H CF ₃ H Me EtNHCO

1-410 CF ₃ H CF ₃ H Me tert-BuOC(=0)

1-411 CI CI CF ₃ H Me H

1-412 CI CI CF ₃ H Me MeCO

1-413 CI CI CF ₃ H Me EtCO

1-414 CI CI CF ₃ H Me cyclo-PrCO

1-415 CI CI CF ₃ H Me CH ₃ SCH ₂ CO

1-416 CI CI CF ₃ H Me CF ₃ CH ₂ CO

1-417 CI CI CF ₃ H Me EtNHCO

1-418 CI CI CF ₃ H Me tert-BuOC(=0)

1-419 CI H CF ₃ H Me H

1-420 CI H CF ₃ H Me MeCO

1-421 CI H CF ₃ H Me EtCO

1-422 CI H CF ₃ H Me cyclo-PrCO

Wherein, X ¹ , X ⁵ , Y ¹ , Y ² , Y ⁴ and R ³ represent hydrogen.

Table 2

Compound No. X ² X ³ X ⁴ R ⁴ m

2-1 CI H CI H 1 Compound No. X ² X ³ X ⁴ R ⁴ m

2-37 CI CI CI CH ₃ SOCH ₂ CO ¹

2-38 CI CI CI CH ₃ S0 ₂ CH ₂ CO ¹

2-39 CI CI CI CH ₃ OCH ₂ CH ₂ CO ¹

2-40 CI CI CI CH ₃ OCH(Me)CH ₂ CO ¹

2-41 CI CI CI EtNHCO ¹

2-42 CI CI CI tert-BuOC(=0) ¹

2-43 CF ₃ H H H ¹

2-44 CF ₃ H H MeCO ¹

2-45 CF ₃ H H EtCO ¹

2-46 CF ₃ H H n-PrCO ¹

2-47 CF ₃ H H cyclo-PrCO ¹

2-48 CF ₃ H H cyclo-PrCH ₂ CO ¹

2-49 CF ₃ H H CF ₃ CH ₂ CO ¹

2-50 CF ₃ H H CH ₃ SCH ₂ CO ¹

2-51 CF ₃ H H CH ₃ SOCH ₂ CO ¹

2-52 CF ₃ H H CH ₃ S0 ₂ CH ₂ CO ¹

2-53 CF ₃ H H CH ₃ OCH ₂ CH ₂ CO ¹

2-54 CF ₃ H H CH ₃ OCH(Me)CH ₂ CO ¹

2-55 CF ₃ H H EtNHCO ¹

2-56 CF ₃ H H tert-BuOC(=0) ¹

2-57 CF ₃ H CF ₃ H ¹

2-58 CF ₃ H CF ₃ MeCO ¹

2-59 CF ₃ H CF ₃ EtCO ¹

2-60 CF ₃ H CF ₃ n-PrCO ¹

2-61 CF ₃ H CF ₃ cyclo-PrCO ¹

2-62 CF ₃ H CF ₃ cyclo-PrCH ₂ CO ¹

2-63 CF ₃ H CF ₃ CF ₃ CH ₂ CO ¹

2-64 CF ₃ H CF ₃ CH ₃ SCH ₂ CO ¹

2-65 CF ₃ H CF ₃ CH ₃ SOCH ₂ CO ¹

2-66 CF ₃ H CF ₃ CH ₃ S0 ₂ CH ₂ CO ¹

2-67 CF ₃ H CF ₃ CH ₃ OCH ₂ CH ₂ CO ¹

2-68 CF ₃ H CF ₃ CH ₃ OCH(Me)CH ₂ CO ¹

2-69 CF ₃ H CF ₃ EtNHCO ¹

2-70 CF ₃ H CF ₃ tert-BuOC(=0) ¹

2-71 CI CI CF ₃ H ¹ Compound No. X ² X ³ X ⁴ R ⁴ m

2-72 CI CI CF ₃ MeCO ¹

2-73 CI CI CF ₃ EtCO ¹

2-74 CI CI CF ₃ cyclo-PrCO ¹

2-75 CI CI CF ₃ CH ₃ SCH ₂ CO ¹

2-76 CI CI CF ₃ CF ₃ CH ₂ CO ¹

2-77 CI CI CF ₃ EtNHCO ¹

2-78 CI CI CF ₃ tert-BuOC(=0) ¹

2-79 CI H CF ₃ H ¹

2-80 CI H CF ₃ MeCO ¹

2-81 CI H CF ₃ EtCO ¹

2-82 CI H CF ₃ cyclo-PrCO ¹

2-83 CI H CF ₃ CH ₃ SCH ₂ CO ¹

2-84 CI H CF ₃ CF ₃ CH ₂ CO ¹

2-85 CI H CF ₃ EtNHCO ¹

2-86 CI H CF ₃ tert-BuOC(=0) ¹

2-87 F H CF ₃ H ¹

2-88 F H CF ₃ MeCO ¹

2-89 F H CF ₃ EtCO ¹

2-90 F H CF ₃ cyclo-PrCO ¹

2-91 F H CF ₃ CH ₃ SCH ₂ CO ¹

2-92 F H CF ₃ CF ₃ CH ₂ CO ¹

2-93 F H CF ₃ EtNHCO ¹

2-94 F H CF ₃ tert-BuOC(=0) ¹

2-95 H F CF ₃ H ¹

2-96 H F CF ₃ MeCO ¹

2-97 H F CF ₃ EtCO ¹

2-98 H F CF ₃ cyclo-PrCO ¹

2-99 H F CF ₃ CH ₃ SCH ₂ CO ¹

2-100 H F CF ₃ CF ₃ CH ₂ CO ¹

2-101 H F CF ₃ EtNHCO ¹

2-102 H F CF ₃ tert-BuOC(=0) ¹

2-103 CI H CI H 2

2-104 CI H CI MeCO 2

2-105 CI H CI EtCO 2

2-106 CI H CI n-PrCO 2 Compound No. X ² X ³ X ⁴ R ⁴ m

2-142 CI CI CI CH ₃ OCH(Me)CH ₂ CO 2

2-143 CI CI CI EtNHCO 2

2-144 CI CI CI tert-BuOC(=0) 2

2-145 CF ₃ H H H 2

2-146 CF ₃ H H MeCO 2

2-147 CF ₃ H H EtCO 2

2-148 CF ₃ H H n-PrCO 2

2-149 CF ₃ H H cyclo-PrCO 2

2-150 CF ₃ H H cyclo-PrCH ₂ CO 2

2-151 CF ₃ H H CF ₃ CH ₂ CO 2

2-152 CF ₃ H H CH ₃ SCH ₂ CO 2

2-153 CF ₃ H H CH ₃ SOCH ₂ CO 2

2-154 CF ₃ H H CH ₃ S0 ₂ CH ₂ CO 2

2-155 CF ₃ H H CH ₃ OCH ₂ CH ₂ CO 2

2-156 CF ₃ H H CH ₃ OCH(Me)CH ₂ CO 2

2-157 CF ₃ H H EtNHCO 2

2-158 CF ₃ H H tert-BuOC(=0) 2

2-159 CF ₃ H CF ₃ H 2

2-160 CF ₃ H CF ₃ MeCO 2

2-161 CF ₃ H CF ₃ EtCO 2

2-162 CF ₃ H CF ₃ n-PrCO 2

2-163 CF ₃ H CF ₃ cyclo-PrCO 2

2-164 CF ₃ H CF ₃ cyclo-PrCH ₂ CO 2

2-165 CF ₃ H CF ₃ CF ₃ CH ₂ CO 2

2-166 CF ₃ H CF ₃ CH ₃ SCH ₂ CO 2

2-167 CF ₃ H CF ₃ CH ₃ SOCH ₂ CO 2

2-168 CF ₃ H CF ₃ CH ₃ S0 ₂ CH ₂ CO 2

2-169 CF ₃ H CF ₃ CH ₃ OCH ₂ CH ₂ CO 2

2-170 CF ₃ H CF ₃ CH ₃ OCH(Me)CH ₂ CO 2

2-171 CF ₃ H CF ₃ EtNHCO 2

2-172 CF ₃ H CF ₃ tert-BuOC(=0) 2

2-173 CI CI CF ₃ H 2

2-174 CI CI CF ₃ MeCO 2

2-175 CI CI CF ₃ EtCO 2

2-176 CI CI CF ₃ cyclo-PrCO 2

Wherein, X ¹ , X ⁵ , Y ¹ , Y ² , Υ ⁴ , R ² and R ³ represent hydrogen.

Table 3

Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

3-1 CI H CI CF ₃ H H

3-2 CI H CI CF ₃ H MeCO

3-3 CI H CI CF ₃ H EtCO

3-4 CI H CI CF ₃ H n-PrCO

3-5 CI H CI CF ₃ H cyclo-PrCO

3-6 CI H CI CF ₃ H cyclo-PrCH ₂ CO

3-7 CI H CI CF ₃ H CF ₃ CH ₂ CO

3-8 CI H CI CF ₃ H CH ₃ SCH ₂ CO

3-9 CI H CI CF ₃ H CH ₃ SOCH ₂ CO

3-10 CI H CI CF ₃ H CH ₃ S0 ₂ CH ₂ CO

3-11 CI H CI CF ₃ H CH ₃ OCH ₂ CH ₂ CO

3-12 CI H CI CF ₃ H CH ₃ OCH(Me)CH ₂ CO

3-13 CI H CI CF ₃ H EtNHCO

3-14 CI H CI CF ₃ H tert-BuOC(=0)

3-15 CI CI CI CF ₃ H H

3-16 CI CI CI CF ₃ H MeCO

3-17 CI CI CI CF ₃ H EtCO

3-18 CI CI CI CF ₃ H n-PrCO

3-19 CI CI CI CF ₃ H cyclo-PrCO

3-20 CI CI CI CF ₃ H cyclo-PrCH ₂ CO

3-21 CI CI CI CF ₃ H CF ₃ CH ₂ CO

3-22 CI CI CI CF ₃ H CH ₃ SCH ₂ CO

3-23 CI CI CI CF ₃ H CH ₃ SOCH ₂ CO

3-24 CI CI CI CF ₃ H CH ₃ S0 ₂ CH ₂ CO

3-25 CI CI CI CF ₃ H CH ₃ OCH ₂ CH ₂ CO

3-26 CI CI CI CF ₃ H CH ₃ OCH(Me)CH ₂ CO

3-27 CI CI CI CF ₃ H EtNHCO

3-28 CI CI CI CF ₃ H tert-BuOC(=0) Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

3-29 CI CI CI CI H H

3-30 CI CI CI CI H MeCO

3-31 CI CI CI CI H EtCO

3-32 CI CI CI CI H n-PrCO

3-33 CI CI CI CI H cyclo-PrCO

3-34 CI CI CI CI H cyclo-PrCH ₂ CO

3-35 CI CI CI CI H CF3CH2CO

3-36 CI CI CI CI H CH3SCH2CO

3-37 CI CI CI CI H CH3SOCH2CO

3-38 CI CI CI CI H CH3SO2CH2CO

3-39 CI CI CI CI H CH3OCH2CH2CO

3-40 CI CI CI CI H CH ₃ OCH(Me)CH ₂ CO

3-41 CI CI CI CI H EtNHCO

3-42 CI CI CI CI H tert-BuOC(=0)

3-43 CI CI CI Me H H

3-44 CI CI CI Me H MeCO

3-45 CI CI CI Me H EtCO

3-46 CI CI CI Me H n-PrCO

3-47 CI CI CI Me H cyclo-PrCO

3-48 CI CI CI Me H cyclo-PrCH ₂ CO

3-49 CI CI CI Me H CF3CH2CO

3-50 CI CI CI Me H CH3SCH2CO

3-51 CI CI CI Me H CH3SOCH2CO

3-52 CI CI CI Me H CH3SO2CH2CO

3-53 CI CI CI Me H CH3OCH2CH2CO

3-54 CI CI CI Me H CH ₃ OCH(Me)CH ₂ CO

3-55 CI CI CI Me H EtNHCO

3-56 CI CI CI Me H tert-BuOC(=0)

3-57 CI CI CI H H H

3-58 CI CI CI H H MeCO

3-59 CI CI CI H H EtCO

3-60 CI CI CI H H n-PrCO

3-61 CI CI CI H H cyclo-PrCO

3-62 CI CI CI H H cyclo-PrCH ₂ CO

3-63 CI CI CI H H CF3CH2CO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

3-64 CI CI CI H H CH ₃ SCH ₂ CO

3-65 CI CI CI H H CH ₃ SOCH ₂ CO

3-66 CI CI CI H H CH ₃ S0 ₂ CH ₂ CO

3-67 CI CI CI H H CH ₃ OCH ₂ CH ₂ CO

3-68 CI CI CI H H CH ₃ OCH(Me)CH ₂ CO

3-69 CI CI CI H H EtNHCO

3-70 CI CI CI H H tert-BuOC(=0)

3-71 CF ₃ H H CF ₃ H H

3-72 CF ₃ H H CF ₃ H MeCO

3-73 CF ₃ H H CF ₃ H EtCO

3-74 CF ₃ H H CF ₃ H n-PrCO

3-75 CF ₃ H H CF ₃ H cyclo-PrCO

3-76 CF ₃ H H CF ₃ H cyclo-PrCH ₂ CO

3-77 CF ₃ H H CF ₃ H CF ₃ CH ₂ CO

3-78 CF ₃ H H CF ₃ H CH ₃ SCH ₂ CO

3-79 CF ₃ H H CF ₃ H CH ₃ SOCH ₂ CO

3-80 CF ₃ H H CF ₃ H CH ₃ S0 ₂ CH ₂ CO

3-81 CF ₃ H H CF ₃ H CH ₃ OCH ₂ CH ₂ CO

3-82 CF ₃ H H CF ₃ H CH ₃ OCH(Me)CH ₂ CO

3-83 CF ₃ H H CF ₃ H EtNHCO

3-84 CF ₃ H H CF ₃ H tert-BuOC(=0)

3-85 CF ₃ H H CI H H

3-86 CF ₃ H H CI H MeCO

3-87 CF ₃ H H CI H EtCO

3-88 CF ₃ H H CI H n-PrCO

3-89 CF ₃ H H CI H cyclo-PrCO

3-90 CF ₃ H H CI H cyclo-PrCH ₂ CO

3-91 CF ₃ H H CI H CF ₃ CH ₂ CO

3-92 CF ₃ H H CI H CH ₃ SCH ₂ CO

3-93 CF ₃ H H CI H CH ₃ SOCH ₂ CO

3-94 CF ₃ H H CI H CH ₃ S0 ₂ CH ₂ CO

3-95 CF ₃ H H CI H CH ₃ OCH ₂ CH ₂ CO

3-96 CF ₃ H H CI H CH ₃ OCH(Me)CH ₂ CO

3-97 CF ₃ H H CI H EtNHCO

3-98 CF ₃ H H CI H tert-BuOC(=0) Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

3-99 CF ₃ H H Me H H

3-100 CF ₃ H H Me H MeCO

3-101 CF ₃ H H Me H EtCO

3-102 CF ₃ H H Me H n-PrCO

3-103 CF ₃ H H Me H cyclo-PrCO

3-104 CF ₃ H H Me H cyclo-PrCH ₂ CO

3-105 CF ₃ H H Me H CF ₃ CH ₂ CO

3-106 CF ₃ H H Me H CH ₃ SCH ₂ CO

3-107 CF ₃ H H Me H CH ₃ SOCH ₂ CO

3-108 CF ₃ H H Me H CH ₃ S0 ₂ CH ₂ CO

3-109 CF ₃ H H Me H CH ₃ OCH ₂ CH ₂ CO

3-110 CF ₃ H H Me H CH ₃ OCH(Me)CH ₂ CO

3-111 CF ₃ H H Me H EtNHCO

3-112 CF ₃ H H Me H tert-BuOC(=0)

3-113 CF ₃ H H H H H

3-114 CF ₃ H H H H MeCO

3-115 CF ₃ H H H H EtCO

3-116 CF ₃ H H H H n-PrCO

3-117 CF ₃ H H H H cyclo-PrCO

3-118 CF ₃ H H H H cyclo-PrCH ₂ CO

3-119 CF ₃ H H H H CF ₃ CH ₂ CO

3-120 CF ₃ H H H H CH ₃ SCH ₂ CO

3-121 CF ₃ H H H H CH ₃ SOCH ₂ CO

3-122 CF ₃ H H H H CH ₃ S0 ₂ CH ₂ CO

3-123 CF ₃ H H H H CH ₃ OCH ₂ CH ₂ CO

3-124 CF ₃ H H H H CH ₃ OCH(Me)CH ₂ CO

3-125 CF ₃ H H H H EtNHCO

3-126 CF ₃ H H H H tert-BuOC(=0)

3-127 CF ₃ H CF ₃ CF ₃ H H

3-128 CF ₃ H CF ₃ CF ₃ H MeCO

3-129 CF ₃ H CF ₃ CF ₃ H EtCO

3-130 CF ₃ H CF ₃ CF ₃ H n-PrCO

3-131 CF ₃ H CF ₃ CF ₃ H cyclo-PrCO

3-132 CF ₃ H CF ₃ CF ₃ H cyclo-PrCH ₂ CO

3-133 CF ₃ H CF ₃ CF ₃ H CF ₃ CH ₂ CO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

3-134 CF ₃ H CF ₃ CF ₃ H CH ₃ SCH ₂ CO

3-135 CF ₃ H CF ₃ CF ₃ H CH ₃ SOCH ₂ CO

3-136 CF ₃ H CF ₃ CF ₃ H CH ₃ S0 ₂ CH ₂ CO

3-137 CF ₃ H CF ₃ CF ₃ H CH ₃ OCH ₂ CH ₂ CO

3-138 CF ₃ H CF ₃ CF ₃ H CH ₃ OCH(Me)CH ₂ CO

3-139 CF ₃ H CF ₃ CF ₃ H EtNHCO

3-140 CF ₃ H CF ₃ CF ₃ H tert-BuOC(=0)

3-141 CF ₃ H CF ₃ CI H H

3-142 CF ₃ H CF ₃ CI H MeCO

3-143 CF ₃ H CF ₃ CI H EtCO

3-144 CF ₃ H CF ₃ CI H n-PrCO

3-145 CF ₃ H CF ₃ CI H cyclo-PrCO

3-146 CF ₃ H CF ₃ CI H cyclo-PrCH ₂ CO

3-147 CF ₃ H CF ₃ CI H CF ₃ CH ₂ CO

3-148 CF ₃ H CF ₃ CI H CH ₃ SCH ₂ CO

3-149 CF ₃ H CF ₃ CI H CH ₃ SOCH ₂ CO

3-150 CF ₃ H CF ₃ CI H CH ₃ S0 ₂ CH ₂ CO

3-151 CF ₃ H CF ₃ CI H CH ₃ OCH ₂ CH ₂ CO

3-152 CF ₃ H CF ₃ CI H CH ₃ OCH(Me)CH ₂ CO

3-153 CF ₃ H CF ₃ CI H EtNHCO

3-154 CF ₃ H CF ₃ CI H tert-BuOC(=0)

3-155 CF ₃ H CF ₃ Me H H

3-156 CF ₃ H CF ₃ Me H MeCO

3-157 CF ₃ H CF ₃ Me H EtCO

3-158 CF ₃ H CF ₃ Me H n-PrCO

3-159 CF ₃ H CF ₃ Me H cyclo-PrCO

3-160 CF ₃ H CF ₃ Me H cyclo-PrCH ₂ CO

3-161 CF ₃ H CF ₃ Me H CF ₃ CH ₂ CO

3-162 CF ₃ H CF ₃ Me H CH ₃ SCH ₂ CO

3-163 CF ₃ H CF ₃ Me H CH ₃ SOCH ₂ CO

3-164 CF ₃ H CF ₃ Me H CH ₃ S0 ₂ CH ₂ CO

3-165 CF ₃ H CF ₃ Me H CH ₃ OCH ₂ CH ₂ CO

3-166 CF ₃ H CF ₃ Me H CH ₃ OCH(Me)CH ₂ CO

3-167 CF ₃ H CF ₃ Me H EtNHCO

3-168 CF ₃ H CF ₃ Me H tert-BuOC(=0) Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

3-169 CF ₃ H CF ₃ H H H

3-170 CF ₃ H CF ₃ H H MeCO

3-171 CF ₃ H CF ₃ H H EtCO

3-172 CF ₃ H CF ₃ H H n-PrCO

3-173 CF ₃ H CF ₃ H H cyclo-PrCO

3-174 CF ₃ H CF ₃ H H cyclo-PrCH ₂ CO

3-175 CF ₃ H CF ₃ H H CF ₃ CH ₂ CO

3-176 CF ₃ H CF ₃ H H CH ₃ SCH ₂ CO

3-177 CF ₃ H CF ₃ H H CH ₃ SOCH ₂ CO

3-178 CF ₃ H CF ₃ H H CH ₃ S0 ₂ CH ₂ CO

3-179 CF ₃ H CF ₃ H H CH ₃ OCH ₂ CH ₂ CO

3-180 CF ₃ H CF ₃ H H CH ₃ OCH(Me)CH ₂ CO

3-181 CF ₃ H CF ₃ H H EtNHCO

3-182 CF ₃ H CF ₃ H H tert-BuOC(=0)

3-183 CI CI CF ₃ CF ₃ H H

3-184 CI CI CF ₃ CF ₃ H MeCO

3-185 CI CI CF ₃ CF ₃ H EtCO

3-186 CI CI CF ₃ CF ₃ H cyclo-PrCO

3-187 CI CI CF ₃ CF ₃ H CH ₃ SCH ₂ CO

3-188 CI CI CF ₃ CF ₃ H CF ₃ CH ₂ CO

3-189 CI CI CF ₃ CF ₃ H EtNHCO

3-190 CI CI CF ₃ CF ₃ H tert-BuOC(=0)

3-191 CI H CF ₃ CF ₃ H H

3-192 CI H CF ₃ CF ₃ H MeCO

3-193 CI H CF ₃ CF ₃ H EtCO

3-194 CI H CF ₃ CF ₃ H cyclo-PrCO

3-195 CI H CF ₃ CF ₃ H CH ₃ SCH ₂ CO

3-196 CI H CF ₃ CF ₃ H CF ₃ CH ₂ CO

3-197 CI H CF ₃ CF ₃ H EtNHCO

3-198 CI H CF ₃ CF ₃ H tert-BuOC(=0)

3-199 F H CF ₃ CF ₃ H H

3-200 F H CF ₃ CF ₃ H MeCO

3-201 F H CF ₃ CF ₃ H EtCO

3-202 F H CF ₃ CF ₃ H cyclo-PrCO

3-203 F H CF ₃ CF ₃ H CH ₃ SCH ₂ CO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

3-204 F H CF ₃ CF ₃ H CF ₃ CH ₂ CO

3-205 F H CF ₃ CF ₃ H EtNHCO

3-206 F H CF ₃ CF ₃ H tert-BuOC(=0)

3-207 H F CF ₃ CF ₃ H H

3-208 H F CF ₃ CF ₃ H MeCO

3-209 H F CF ₃ CF ₃ H EtCO

3-210 H F CF ₃ CF ₃ H cyclo-PrCO

3-211 H F CF ₃ CF ₃ H CH ₃ SCH ₂ CO

3-212 H F CF ₃ CF ₃ H CF ₃ CH ₂ CO

3-213 H F CF ₃ CF ₃ H EtNHCO

3-214 H F CF ₃ CF ₃ H tert-BuOC(=0)

3-215 CI H CI Br H H

3-216 CI H CI Br H MeCO

3-217 CI H CI Br H EtCO

3-218 CI H CI Br H n-PrCO

3-219 CI H CI Br H cyclo-PrCO

3-220 CI H CI Br H cyclo-PrCH ₂ CO

3-221 CI H CI Br H CF ₃ CH ₂ CO

3-222 CI H CI Br H CH ₃ SCH ₂ CO

3-223 CI H CI Br H CH ₃ SOCH ₂ CO

3-224 CI H CI Br H CH ₃ S0 ₂ CH ₂ CO

3-225 CI H CI Br H CH ₃ OCH ₂ CH ₂ CO

3-226 CI H CI Br H CH ₃ OCH(Me)CH ₂ CO

3-227 CI H CI Br H EtNHCO

3-228 CI H CI Br H tert-BuOC(=0)

3-229 CI CI CI Br H H

3-230 CI CI CI Br H MeCO

3-231 CI CI CI Br H EtCO

3-232 CI CI CI Br H n-PrCO

3-233 CI CI CI Br H cyclo-PrCO

3-234 CI CI CI Br H cyclo-PrCH ₂ CO

3-235 CI CI CI Br H CF ₃ CH ₂ CO

3-236 CI CI CI Br H CH ₃ SCH ₂ CO

3-237 CI CI CI Br H CH ₃ SOCH ₂ CO

3-238 CI CI CI Br H CH ₃ S0 ₂ CH ₂ CO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

3-239 CI CI CI Br H CH ₃ OCH ₂ CH ₂ CO

3-240 CI CI CI Br H CH ₃ OCH(Me)CH ₂ CO

3-241 CI CI CI Br H EtNHCO

3-242 CI CI CI Br H tert-BuOC(=0)

3-243 CF ₃ H H Br H H

3-244 CF ₃ H H Br H MeCO

3-245 CF ₃ H H Br H EtCO

3-246 CF ₃ H H Br H n-PrCO

3-247 CF ₃ H H Br H cyclo-PrCO

3-248 CF ₃ H H Br H cyclo-PrCH ₂ CO

3-249 CF ₃ H H Br H CF ₃ CH ₂ CO

3-250 CF ₃ H H Br H CH ₃ SCH ₂ CO

3-251 CF ₃ H H Br H CH ₃ SOCH ₂ CO

3-252 CF ₃ H H Br H CH ₃ S0 ₂ CH ₂ CO

3-253 CF ₃ H H Br H CH ₃ OCH ₂ CH ₂ CO

3-254 CF ₃ H H Br H CH ₃ OCH(Me)CH ₂ CO

3-255 CF ₃ H H Br H EtNHCO

3-256 CF ₃ H H Br H tert-BuOC(=0)

3-257 CF ₃ H CF ₃ Br H H

3-258 CF ₃ H CF ₃ Br H MeCO

3-259 CF ₃ H CF ₃ Br H EtCO

3-260 CF ₃ H CF ₃ Br H n-PrCO

3-261 CF ₃ H CF ₃ Br H cyclo-PrCO

3-262 CF ₃ H CF ₃ Br H cyclo-PrCH ₂ CO

3-263 CF ₃ H CF ₃ Br H CF ₃ CH ₂ CO

3-264 CF ₃ H CF ₃ Br H CH ₃ SCH ₂ CO

3-265 CF ₃ H CF ₃ Br H CH ₃ SOCH ₂ CO

3-266 CF ₃ H CF ₃ Br H CH ₃ S0 ₂ CH ₂ CO

3-267 CF ₃ H CF ₃ Br H CH ₃ OCH ₂ CH ₂ CO

3-268 CF ₃ H CF ₃ Br H CH ₃ OCH(Me)CH ₂ CO

3-269 CF ₃ H CF ₃ Br H EtNHCO

3-270 CF ₃ H CF ₃ Br H tert-BuOC(=0)

3-271 Br H Br CF ₃ H H

3-272 Br H Br CF ₃ H MeCO

3-273 Br H Br CF ₃ H EtCO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

3-274 Br H Br CF ₃ H n-PrCO

3-275 Br H Br CF ₃ H cyclo-PrCO

3-276 Br H Br CF ₃ H cyclo-PrCH ₂ CO

3-277 Br H Br CF ₃ H CF ₃ CH ₂ CO

3-278 Br H Br CF ₃ H CH ₃ SCH ₂ CO

3-279 Br H Br CF ₃ H CH ₃ SOCH ₂ CO

3-280 Br H Br CF ₃ H CH ₃ S0 ₂ CH ₂ CO

3-281 Br H Br CF ₃ H CH ₃ OCH ₂ CH ₂ CO

3-282 Br H Br CF ₃ H CH ₃ OCH(Me)CH ₂ CO

3-283 Br H Br CF ₃ H EtNHCO

3-284 Br H Br CF ₃ H tert-BuOC(=0)

3-285 Br H Br CI H H

3-286 Br H Br CI H MeCO

3-287 Br H Br CI H EtCO

3-288 Br H Br CI H n-PrCO

3-289 Br H Br CI H cyclo-PrCO

3-290 Br H Br CI H cyclo-PrCH ₂ CO

3-291 Br H Br CI H CF ₃ CH ₂ CO

3-292 Br H Br CI H CH ₃ SCH ₂ CO

3-293 Br H Br CI H CH ₃ SOCH ₂ CO

3-294 Br H Br CI H CH ₃ S0 ₂ CH ₂ CO

3-295 Br H Br CI H CH ₃ OCH ₂ CH ₂ CO

3-296 Br H Br CI H CH ₃ OCH(Me)CH ₂ CO

3-297 Br H Br CI H EtNHCO

3-298 Br H Br CI H tert-BuOC(=0)

3-299 Br H Br Br H H

3-300 Br H Br Br H MeCO

3-301 Br H Br Br H EtCO

3-302 Br H Br Br H n-PrCO

3-303 Br H Br Br H cyclo-PrCO

3-304 Br H Br Br H cyclo-PrCH ₂ CO

3-305 Br H Br Br H CF ₃ CH ₂ CO

3-306 Br H Br Br H CH ₃ SCH ₂ CO

3-307 Br H Br Br H CH ₃ SOCH ₂ CO

3-308 Br H Br Br H CH ₃ S0 ₂ CH ₂ CO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

3-344 CI H CI H Me n-PrCO

3-345 CI H CI H Me cyclo-PrCO

3-345-a CI H CI H Me cyclo-PrCO

3-346 CI H CI H Me cyclo-PrCH ₂ CO

3-347 CI H CI H Me CF3CH2CO

3-348 CI H CI H Me CH3SCH2CO

3-349 CI H CI H Me CH3SOCH2CO

3-350 CI H CI H Me CH3SO2CH2CO

3-351 CI H CI H Me CH3OCH2CH2CO

3-352 CI H CI H Me CH ₃ OCH(Me)CH ₂ CO

3-353 CI H CI H Me EtNHCO

3-354 CI H CI H Me tert-BuOC(=0)

3-355 Br H Br H Me H

3-356 Br H Br H Me MeCO

3-357 Br H Br H Me EtCO

3-358 Br H Br H Me n-PrCO

3-359 Br H Br H Me cyclo-PrCO

3-360 Br H Br H Me cyclo-PrCH ₂ CO

3-361 Br H Br H Me CF3CH2CO

3-362 Br H Br H Me CH3SCH2CO

3-363 Br H Br H Me CH3SOCH2CO

3-364 Br H Br H Me CH3SO2CH2CO

3-365 Br H Br H Me CH3OCH2CH2CO

3-366 Br H Br H Me CH ₃ OCH(Me)CH ₂ CO

3-367 Br H Br H Me EtNHCO

3-368 Br H Br H Me tert-BuOC(=0)

3-369 CI CI CI H Me H

3-370 CI CI CI H Me MeCO

3-370-a CI CI CI H Me MeCO

3-371 CI CI CI H Me EtCO

3-371-a CI CI CI H Me EtCO

3-371-b CI CI CI H Me EtCO

3-372 CI CI CI H Me n-PrCO

3-373 CI CI CI H Me cyclo-PrCO

3-373-a CI CI CI H Me cyclo-PrCO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

3-374 CI CI CI H Me cyclo-PrCH ₂ CO

3-374-a CI CI CI H Me cyclo-PrCH ₂ CO

3-375 CI CI CI H Me CF ₃ CH ₂ CO

3-375-a CI CI CI H Me CF ₃ CH ₂ CO

3-376 CI CI CI H Me CH ₃ SCH ₂ CO

3-377 CI CI CI H Me CH ₃ SOCH ₂ CO

3-378 CI CI CI H Me CH ₃ S0 ₂ CH ₂ CO

3-379 CI CI CI H Me CH ₃ OCH ₂ CH ₂ CO

3-379-a CI CI CI H Me CH ₃ OCH ₂ CH ₂ CO

3-380 CI CI CI H Me CH ₃ OCH(Me)CH ₂ CO

3-381 CI CI CI H Me EtNHCO

3-382 CI CI CI H Me tert-BuOC(=0)

3-383 CF ₃ H H H Me H

3-384 CF ₃ H H H Me MeCO

3-385 CF ₃ H H H Me EtCO

3-386 CF ₃ H H H Me n-PrCO

3-387 CF ₃ H H H Me cyclo-PrCO

3-388 CF ₃ H H H Me cyclo-PrCH ₂ CO

3-389 CF ₃ H H H Me CF ₃ CH ₂ CO

3-390 CF ₃ H H H Me CH ₃ SCH ₂ CO

3-391 CF ₃ H H H Me CH ₃ SOCH ₂ CO

3-392 CF ₃ H H H Me CH ₃ S0 ₂ CH ₂ CO

3-393 CF ₃ H H H Me CH ₃ OCH ₂ CH ₂ CO

3-394 CF ₃ H H H Me CH ₃ OCH(Me)CH ₂ CO

3-395 CF ₃ H H H Me EtNHCO

3-396 CF ₃ H H H Me tert-BuOC(=0)

3-397 CF ₃ H CF ₃ H Me H

3-398 CF ₃ H CF ₃ H Me MeCO

3-398-a CF ₃ H CF ₃ H Me MeCO

3-399 CF ₃ H CF ₃ H Me EtCO

3-399-a CF ₃ H CF ₃ H Me EtCO

3-399-b CF ₃ H CF ₃ H Me EtCO

3-400 CF ₃ H CF ₃ H Me n-PrCO

3-401 CF ₃ H CF ₃ H Me cyclo-PrCO

3-401-a CF ₃ H CF ₃ H Me cyclo-PrCO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

3-402 CF ₃ H CF ₃ H Me cyclo-PrCH ₂ CO

3-402-a CF ₃ H CF ₃ H Me cyclo-PrCH ₂ CO

3-403 CF ₃ H CF ₃ H Me CF ₃ CH ₂ CO

3-403-a CF ₃ H CF ₃ H Me CF ₃ CH ₂ CO

3-404 CF ₃ H CF ₃ H Me CH ₃ SCH ₂ CO

3-405 CF ₃ H CF ₃ H Me CH ₃ SOCH ₂ CO

3-406 CF ₃ H CF ₃ H Me CH ₃ S0 ₂ CH ₂ CO

3-407 CF ₃ H CF ₃ H Me CH ₃ OCH ₂ CH ₂ CO

3-407-a CF ₃ H CF ₃ H Me CH ₃ OCH ₂ CH ₂ CO

3-408 CF ₃ H CF ₃ H Me CH ₃ OCH(Me)CH ₂ CO

3-409 CF ₃ H CF ₃ H Me EtNHCO

3-410 CF ₃ H CF ₃ H Me tert-BuOC(=0)

3-411 CI CI CF ₃ H Me H

3-412 CI CI CF ₃ H Me MeCO

3-413 CI CI CF ₃ H Me EtCO

3-414 CI CI CF ₃ H Me cyclo-PrCO

3-415 CI CI CF ₃ H Me CH ₃ SCH ₂ CO

3-416 CI CI CF ₃ H Me CF ₃ CH ₂ CO

3-417 CI CI CF ₃ H Me EtNHCO

3-418 CI CI CF ₃ H Me tert-BuOC(=0)

3-419 CI H CF ₃ H Me H

3-420 CI H CF ₃ H Me MeCO

3-421 CI H CF ₃ H Me EtCO

3-422 CI H CF ₃ H Me cyclo-PrCO

3-423 CI H CF ₃ H Me CH ₃ SCH ₂ CO

3-424 CI H CF ₃ H Me CF ₃ CH ₂ CO

3-425 CI H CF ₃ H Me EtNHCO

3-426 CI H CF ₃ H Me tert-BuOC(=0)

3-427 F H CF ₃ H Me H

3-428 F H CF ₃ H Me MeCO

3-429 F H CF ₃ H Me EtCO

3-430 F H CF ₃ H Me cyclo-PrCO

3-431 F H CF ₃ H Me CH ₃ SCH ₂ CO

3-432 F H CF ₃ H Me CF ₃ CH ₂ CO

3-433 F H CF ₃ H Me EtNHCO

Wherein, X ¹ , X ⁵ , Y ¹ , Y ² , Y ⁴ and R ³ represent hydrogen.

Table 4

Compound No. X ² X ³ X ⁴ R ⁴ m

4-13 CI H CI EtNHCO ¹

4-14 CI H CI tert-BuOC(=0) ¹

4-15 Br H Br H ¹

4-16 Br H Br MeCO ¹

4-17 Br H Br EtCO ¹

4-18 Br H Br n-PrCO ¹

4-19 Br H Br cyclo-PrCO ¹

4-20 Br H Br cyclo-PrCH ₂ CO ¹

4-21 Br H Br CF ₃ CH ₂ CO ¹

4-22 Br H Br CH ₃ SCH ₂ CO ¹

4-23 Br H Br CH ₃ SOCH ₂ CO ¹

4-24 Br H Br CH ₃ S0 ₂ CH ₂ CO ¹

4-25 Br H Br CH ₃ OCH ₂ CH ₂ CO ¹

4-26 Br H Br CH ₃ OCH(Me)CH ₂ CO ¹

4-27 Br H Br EtNHCO ¹

4-28 Br H Br tert-BuOC(=0) ¹

4-29 CI CI CI H ¹

4-30 CI CI CI MeCO ¹

4-31 CI CI CI EtCO ¹

4-32 CI CI CI n-PrCO ¹

4-33 CI CI CI cyclo-PrCO ¹

4-34 CI CI CI cyclo-PrCH ₂ CO ¹

4-35 CI CI CI CF ₃ CH ₂ CO ¹

4-36 CI CI CI CH ₃ SCH ₂ CO ¹

4-37 CI CI CI CH ₃ SOCH ₂ CO ¹

4-38 CI CI CI CH ₃ S0 ₂ CH ₂ CO ¹

4-39 CI CI CI CH ₃ OCH ₂ CH ₂ CO ¹

4-40 CI CI CI CH ₃ OCH(Me)CH ₂ CO ¹

4-41 CI CI CI EtNHCO ¹

4-42 CI CI CI tert-BuOC(=0) ¹

4-43 CF ₃ H H H ¹

4-44 CF ₃ H H MeCO ¹

4-45 CF ₃ H H EtCO ¹

4-46 CF ₃ H H n-PrCO ¹

4-47 CF ₃ H H cyclo-PrCO ¹ Compound No. X ² X ³ X ⁴ R ⁴ m

4-48 CF ₃ H H cyclo-PrCH ₂ CO ¹

4-49 CF ₃ H H CF ₃ CH ₂ CO ¹

4-50 CF ₃ H H CH ₃ SCH ₂ CO ¹

4-51 CF ₃ H H CH ₃ SOCH ₂ CO ¹

4-52 CF ₃ H H CH ₃ S0 ₂ CH ₂ CO ¹

4-53 CF ₃ H H CH ₃ OCH ₂ CH ₂ CO ¹

4-54 CF ₃ H H CH ₃ OCH(Me)CH ₂ CO ¹

4-55 CF ₃ H H EtNHCO ¹

4-56 CF ₃ H H tert-BuOC(=0) ¹

4-57 CF ₃ H CF ₃ H ¹

4-58 CF ₃ H CF ₃ MeCO ¹

4-59 CF ₃ H CF ₃ EtCO ¹

4-60 CF ₃ H CF ₃ n-PrCO ¹

4-61 CF ₃ H CF ₃ cyclo-PrCO ¹

4-62 CF ₃ H CF ₃ cyclo-PrCH ₂ CO ¹

4-63 CF ₃ H CF ₃ CF ₃ CH ₂ CO ¹

4-64 CF ₃ H CF ₃ CH ₃ SCH ₂ CO ¹

4-65 CF ₃ H CF ₃ CH ₃ SOCH ₂ CO ¹

4-66 CF ₃ H CF ₃ CH ₃ S0 ₂ CH ₂ CO ¹

4-67 CF ₃ H CF ₃ CH ₃ OCH ₂ CH ₂ CO ¹

4-68 CF ₃ H CF ₃ CH ₃ OCH(Me)CH ₂ CO ¹

4-69 CF ₃ H CF ₃ EtNHCO ¹

4-70 CF ₃ H CF ₃ tert-BuOC(=0) ¹

4-71 CI CI CF ₃ H ¹

4-72 CI CI CF ₃ MeCO ¹

4-73 CI CI CF ₃ EtCO ¹

4-74 CI CI CF ₃ cyclo-PrCO ¹

4-75 CI CI CF ₃ CH ₃ SCH ₂ CO ¹

4-76 CI CI CF ₃ CF ₃ CH ₂ CO ¹

4-77 CI CI CF ₃ EtNHCO ¹

4-78 CI CI CF ₃ tert-BuOC(=0) ¹

4-79 CI H CF ₃ H ¹

4-80 CI H CF ₃ MeCO ¹

4-81 CI H CF ₃ EtCO ¹

4-82 CI H CF ₃ cyclo-PrCO ¹ Compound No. X ² X ³ X ⁴ R ⁴ m

4-83 CI H CF ₃ CH ₃ SCH ₂ CO ¹

4-84 CI H CF ₃ CF ₃ CH ₂ CO ¹

4-85 CI H CF ₃ EtNHCO ¹

4-86 CI H CF ₃ tert-BuOC(=0) ¹

4-87 F H CF ₃ H ¹

4-88 F H CF ₃ MeCO ¹

4-89 F H CF ₃ EtCO ¹

4-90 F H CF ₃ cyclo-PrCO ¹

4-91 F H CF ₃ CH ₃ SCH ₂ CO ¹

4-92 F H CF ₃ CF ₃ CH ₂ CO ¹

4-93 F H CF ₃ EtNHCO ¹

4-94 F H CF ₃ tert-BuOC(=0) ¹

4-95 H F CF ₃ H ¹

4-96 H F CF ₃ MeCO ¹

4-97 H F CF ₃ EtCO ¹

4-98 H F CF ₃ cyclo-PrCO ¹

4-99 H F CF ₃ CH ₃ SCH ₂ CO ¹

4-100 H F CF ₃ CF ₃ CH ₂ CO ¹

4-101 H F CF ₃ EtNHCO ¹

4-102 H F CF ₃ tert-BuOC(=0) ¹

4-103 CI H CI H 2

4-104 CI H CI MeCO 2

4-105 CI H CI EtCO 2

4-106 CI H CI n-PrCO 2

4-107 CI H CI cyclo-PrCO 2

4-108 CI H CI cyclo-PrCH ₂ CO 2

4-109 CI H CI CF ₃ CH ₂ CO 2

4-110 CI H CI CH ₃ SCH ₂ CO 2

4-111 CI H CI CH ₃ SOCH ₂ CO 2

4-112 CI H CI CH ₃ S0 ₂ CH ₂ CO 2

4-113 CI H CI CH ₃ OCH ₂ CH ₂ CO 2

4-114 CI H CI CH ₃ OCH(Me)CH ₂ CO 2

4-115 CI H CI EtNHCO 2

4-116 CI H CI tert-BuOC(=0) 2

4-117 Br H Br H 2 Compound No. X ² X ³ X ⁴ R ⁴ m

4-118 Br H Br MeCO 2

4-119 Br H Br EtCO 2

4-120 Br H Br n-PrCO 2

4-121 Br H Br cyclo-PrCO 2

4-122 Br H Br cyclo-PrCH ₂ CO 2

4-123 Br H Br CF ₃ CH ₂ CO 2

4-124 Br H Br CH ₃ SCH ₂ CO 2

4-125 Br H Br CH ₃ SOCH ₂ CO 2

4-126 Br H Br CH ₃ S0 ₂ CH ₂ CO 2

4-127 Br H Br CH ₃ OCH ₂ CH ₂ CO 2

4-128 Br H Br CH ₃ OCH(Me)CH ₂ CO 2

4-129 Br H Br EtNHCO 2

4-130 Br H Br tert-BuOC(=0) 2

4-131 CI CI CI H 2

4-132 CI CI CI MeCO 2

4-133 CI CI CI EtCO 2

4-134 CI CI CI n-PrCO 2

4-135 CI CI CI cyclo-PrCO 2

4-136 CI CI CI cyclo-PrCH ₂ CO 2

4-137 CI CI CI CF ₃ CH ₂ CO 2

4-138 CI CI CI CH ₃ SCH ₂ CO 2

4-139 CI CI CI CH ₃ SOCH ₂ CO 2

4-140 CI CI CI CH ₃ S0 ₂ CH ₂ CO 2

4-141 CI CI CI CH ₃ OCH ₂ CH ₂ CO 2

4-142 CI CI CI CH ₃ OCH(Me)CH ₂ CO 2

4-143 CI CI CI EtNHCO 2

4-144 CI CI CI tert-BuOC(=0) 2

4-145 CF ₃ H H H 2

4-146 CF ₃ H H MeCO 2

4-147 CF ₃ H H EtCO 2

4-148 CF ₃ H H n-PrCO 2

4-149 CF ₃ H H cyclo-PrCO 2

4-150 CF ₃ H H cyclo-PrCH ₂ CO 2

4-151 CF ₃ H H CF ₃ CH ₂ CO 2

4-152 CF ₃ H H CH ₃ SCH ₂ CO 2 Compound No. X ² X ³ X ⁴ R ⁴ m

4-153 CF ₃ H H CH ₃ SOCH ₂ CO 2

4-154 CF ₃ H H CH ₃ S0 ₂ CH ₂ CO 2

4-155 CF ₃ H H CH ₃ OCH ₂ CH ₂ CO 2

4-156 CF ₃ H H CH ₃ OCH(Me)CH ₂ CO 2

4-157 CF ₃ H H EtNHCO 2

4-158 CF ₃ H H tert-BuOC(=0) 2

4-159 CF ₃ H CF ₃ H 2

4-160 CF ₃ H CF ₃ MeCO 2

4-161 CF ₃ H CF ₃ EtCO 2

4-162 CF ₃ H CF ₃ n-PrCO 2

4-163 CF ₃ H CF ₃ cyclo-PrCO 2

4-164 CF ₃ H CF ₃ cyclo-PrCH ₂ CO 2

4-165 CF ₃ H CF ₃ CF ₃ CH ₂ CO 2

4-166 CF ₃ H CF ₃ CH ₃ SCH ₂ CO 2

4-167 CF ₃ H CF ₃ CH ₃ SOCH ₂ CO 2

4-168 CF ₃ H CF ₃ CH ₃ S0 ₂ CH ₂ CO 2

4-169 CF ₃ H CF ₃ CH ₃ OCH ₂ CH ₂ CO 2

4-170 CF ₃ H CF ₃ CH ₃ OCH(Me)CH ₂ CO 2

4-171 CF ₃ H CF ₃ EtNHCO 2

4-172 CF ₃ H CF ₃ tert-BuOC(=0) 2

4-173 CI CI CF ₃ H 2

4-174 CI CI CF ₃ MeCO 2

4-175 CI CI CF ₃ EtCO 2

4-176 CI CI CF ₃ cyclo-PrCO 2

4-177 CI CI CF ₃ CH ₃ SCH ₂ CO 2

4-178 CI CI CF ₃ CF ₃ CH ₂ CO 2

4-179 CI CI CF ₃ EtNHCO 2

4-180 CI CI CF ₃ tert-BuOC(=0) 2

4-181 CI H CF ₃ H 2

4-182 CI H CF ₃ MeCO 2

4-183 CI H CF ₃ EtCO 2

4-184 CI H CF ₃ cyclo-PrCO 2

4-185 CI H CF ₃ CH ₃ SCH ₂ CO 2

4-186 CI H CF ₃ CF ₃ CH ₂ CO 2

4-187 CI H CF ₃ EtNHCO 2

Wherein, X ¹ , X ⁵ , Y ¹ , Y ² , Y ⁴ , R ² and R ³ represent hydrogen.

Table 5

Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

5-1 CI H CI CF ₃ H H

5-2 CI H CI CF ₃ H MeCO

5-3 CI H CI CF ₃ H EtCO

5-4 CI H CI CF ₃ H n-PrCO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

5-5 CI H CI CF ₃ H cyclo-PrCO

5-6 CI H CI CF ₃ H cyclo-PrCH ₂ CO

5-7 CI H CI CF ₃ H CF ₃ CH ₂ CO

5-8 CI H CI CF ₃ H CH ₃ SCH ₂ CO

5-9 CI H CI CF ₃ H CH ₃ SOCH ₂ CO

5-10 CI H CI CF ₃ H CH ₃ S0 ₂ CH ₂ CO

5-11 CI H CI CF ₃ H CH ₃ OCH ₂ CH ₂ CO

5-12 CI H CI CF ₃ H CH ₃ OCH(Me)CH ₂ CO

5-13 CI H CI CF ₃ H EtNHCO

5-14 CI H CI CF ₃ H tert-BuOC(=0)

5-15 CI CI CI CF ₃ H H

5-16 CI CI CI CF ₃ H MeCO

5-17 CI CI CI CF ₃ H EtCO

5-18 CI CI CI CF ₃ H n-PrCO

5-19 CI CI CI CF ₃ H cyclo-PrCO

5-20 CI CI CI CF ₃ H cyclo-PrCH ₂ CO

5-21 CI CI CI CF ₃ H CF ₃ CH ₂ CO

5-22 CI CI CI CF ₃ H CH ₃ SCH ₂ CO

5-23 CI CI CI CF ₃ H CH ₃ SOCH ₂ CO

5-24 CI CI CI CF ₃ H CH ₃ S0 ₂ CH ₂ CO

5-25 CI CI CI CF ₃ H CH ₃ OCH ₂ CH ₂ CO

5-26 CI CI CI CF ₃ H CH ₃ OCH(Me)CH ₂ CO

5-27 CI CI CI CF ₃ H EtNHCO

5-28 CI CI CI CF ₃ H tert-BuOC(=0)

5-29 CI CI CI CI H H

5-30 CI CI CI CI H MeCO

5-31 CI CI CI CI H EtCO

5-32 CI CI CI CI H n-PrCO

5-33 CI CI CI CI H cyclo-PrCO

5-34 CI CI CI CI H cyclo-PrCH ₂ CO

5-35 CI CI CI CI H CF ₃ CH ₂ CO

5-36 CI CI CI CI H CH ₃ SCH ₂ CO

5-37 CI CI CI CI H CH ₃ SOCH ₂ CO

5-38 CI CI CI CI H CH ₃ S0 ₂ CH ₂ CO

5-39 CI CI CI CI H CH ₃ OCH ₂ CH ₂ CO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

5-40 CI CI CI CI H CH ₃ OCH(Me)CH ₂ CO

5-41 CI CI CI CI H EtNHCO

5-42 CI CI CI CI H tert-BuOC(=0)

5-43 CI CI CI Me H H

5-44 CI CI CI Me H MeCO

5-45 CI CI CI Me H EtCO

5-46 CI CI CI Me H n-PrCO

5-47 CI CI CI Me H cyclo-PrCO

5-48 CI CI CI Me H cyclo-PrCH ₂ CO

5-49 CI CI CI Me H CF ₃ CH ₂ CO

5-50 CI CI CI Me H CH ₃ SCH ₂ CO

5-51 CI CI CI Me H CH ₃ SOCH ₂ CO

5-52 CI CI CI Me H CH ₃ S0 ₂ CH ₂ CO

5-53 CI CI CI Me H CH ₃ OCH ₂ CH ₂ CO

5-54 CI CI CI Me H CH ₃ OCH(Me)CH ₂ CO

5-55 CI CI CI Me H EtNHCO

5-56 CI CI CI Me H tert-BuOC(=0)

5-57 CI CI CI H H H

5-58 CI CI CI H H MeCO

5-59 CI CI CI H H EtCO

5-60 CI CI CI H H n-PrCO

5-61 CI CI CI H H cyclo-PrCO

5-62 CI CI CI H H cyclo-PrCH ₂ CO

5-63 CI CI CI H H CF ₃ CH ₂ CO

5-64 CI CI CI H H CH ₃ SCH ₂ CO

5-65 CI CI CI H H CH ₃ SOCH ₂ CO

5-66 CI CI CI H H CH ₃ S0 ₂ CH ₂ CO

5-67 CI CI CI H H CH ₃ OCH ₂ CH ₂ CO

5-68 CI CI CI H H CH ₃ OCH(Me)CH ₂ CO

5-69 CI CI CI H H EtNHCO

5-70 CI CI CI H H tert-BuOC(=0)

5-71 CF ₃ H H CF ₃ H H

5-72 CF ₃ H H CF ₃ H MeCO

5-73 CF ₃ H H CF ₃ H EtCO

5-74 CF ₃ H H CF ₃ H n-PrCO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

5-75 CF ₃ H H CF ₃ H cyclo-PrCO

5-76 CF ₃ H H CF ₃ H cyclo-PrCH ₂ CO

5-77 CF ₃ H H CF ₃ H CF ₃ CH ₂ CO

5-78 CF ₃ H H CF ₃ H CH ₃ SCH ₂ CO

5-79 CF ₃ H H CF ₃ H CH ₃ SOCH ₂ CO

5-80 CF ₃ H H CF ₃ H CH ₃ S0 ₂ CH ₂ CO

5-81 CF ₃ H H CF ₃ H CH ₃ OCH ₂ CH ₂ CO

5-82 CF ₃ H H CF ₃ H CH ₃ OCH(Me)CH ₂ CO

5-83 CF ₃ H H CF ₃ H EtNHCO

5-84 CF ₃ H H CF ₃ H tert-BuOC(=0)

5-85 CF ₃ H H CI H H

5-86 CF ₃ H H CI H MeCO

5-87 CF ₃ H H CI H EtCO

5-88 CF ₃ H H CI H n-PrCO

5-89 CF ₃ H H CI H cyclo-PrCO

5-90 CF ₃ H H CI H cyclo-PrCH ₂ CO

5-91 CF ₃ H H CI H CF ₃ CH ₂ CO

5-92 CF ₃ H H CI H CH ₃ SCH ₂ CO

5-93 CF ₃ H H CI H CH ₃ SOCH ₂ CO

5-94 CF ₃ H H CI H CH ₃ S0 ₂ CH ₂ CO

5-95 CF ₃ H H CI H CH ₃ OCH ₂ CH ₂ CO

5-96 CF ₃ H H CI H CH ₃ OCH(Me)CH ₂ CO

5-97 CF ₃ H H CI H EtNHCO

5-98 CF ₃ H H CI H tert-BuOC(=0)

5-99 CF ₃ H H Me H H

5-100 CF ₃ H H Me H MeCO

5-101 CF ₃ H H Me H EtCO

5-102 CF ₃ H H Me H n-PrCO

5-103 CF ₃ H H Me H cyclo-PrCO

5-104 CF ₃ H H Me H cyclo-PrCH ₂ CO

5-105 CF ₃ H H Me H CF ₃ CH ₂ CO

5-106 CF ₃ H H Me H CH ₃ SCH ₂ CO

5-107 CF ₃ H H Me H CH ₃ SOCH ₂ CO

5-108 CF ₃ H H Me H CH ₃ S0 ₂ CH ₂ CO

5-109 CF ₃ H H Me H CH ₃ OCH ₂ CH ₂ CO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

5-110 CF ₃ H H Me H CH ₃ OCH(Me)CH ₂ CO

5-111 CF ₃ H H Me H EtNHCO

5-112 CF ₃ H H Me H tert-BuOC(=0)

5-113 CF ₃ H H H H H

5-114 CF ₃ H H H H MeCO

5-115 CF ₃ H H H H EtCO

5-116 CF ₃ H H H H n-PrCO

5-117 CF ₃ H H H H cyclo-PrCO

5-118 CF ₃ H H H H cyclo-PrCH ₂ CO

5-119 CF ₃ H H H H CF ₃ CH ₂ CO

5-120 CF ₃ H H H H CH ₃ SCH ₂ CO

5-121 CF ₃ H H H H CH ₃ SOCH ₂ CO

5-122 CF ₃ H H H H CH ₃ S0 ₂ CH ₂ CO

5-123 CF ₃ H H H H CH ₃ OCH ₂ CH ₂ CO

5-124 CF ₃ H H H H CH ₃ OCH(Me)CH ₂ CO

5-125 CF ₃ H H H H EtNHCO

5-126 CF ₃ H H H H tert-BuOC(=0)

5-127 CF ₃ H CF ₃ CF ₃ H H

5-128 CF ₃ H CF ₃ CF ₃ H MeCO

5-129 CF ₃ H CF ₃ CF ₃ H EtCO

5-130 CF ₃ H CF ₃ CF ₃ H n-PrCO

5-131 CF ₃ H CF ₃ CF ₃ H cyclo-PrCO

5-132 CF ₃ H CF ₃ CF ₃ H cyclo-PrCH ₂ CO

5-133 CF ₃ H CF ₃ CF ₃ H CF ₃ CH ₂ CO

5-134 CF ₃ H CF ₃ CF ₃ H CH ₃ SCH ₂ CO

5-135 CF ₃ H CF ₃ CF ₃ H CH ₃ SOCH ₂ CO

5-136 CF ₃ H CF ₃ CF ₃ H CH ₃ S0 ₂ CH ₂ CO

5-137 CF ₃ H CF ₃ CF ₃ H CH ₃ OCH ₂ CH ₂ CO

5-138 CF ₃ H CF ₃ CF ₃ H CH ₃ OCH(Me)CH ₂ CO

5-139 CF ₃ H CF ₃ CF ₃ H EtNHCO

5-140 CF ₃ H CF ₃ CF ₃ H tert-BuOC(=0)

5-141 CF ₃ H CF ₃ CI H H

5-142 CF ₃ H CF ₃ CI H MeCO

5-143 CF ₃ H CF ₃ CI H EtCO

5-144 CF ₃ H CF ₃ CI H n-PrCO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

5-145 CF ₃ H CF ₃ CI H cyclo-PrCO

5-146 CF ₃ H CF ₃ CI H cyclo-PrCH ₂ CO

5-147 CF ₃ H CF ₃ CI H CF ₃ CH ₂ CO

5-148 CF ₃ H CF ₃ CI H CH ₃ SCH ₂ CO

5-149 CF ₃ H CF ₃ CI H CH ₃ SOCH ₂ CO

5-150 CF ₃ H CF ₃ CI H CH ₃ S0 ₂ CH ₂ CO

5-151 CF ₃ H CF ₃ CI H CH ₃ OCH ₂ CH ₂ CO

5-152 CF ₃ H CF ₃ CI H CH ₃ OCH(Me)CH ₂ CO

5-153 CF ₃ H CF ₃ CI H EtNHCO

5-154 CF ₃ H CF ₃ CI H tert-BuOC(=0)

5-155 CF ₃ H CF ₃ Me H H

5-156 CF ₃ H CF ₃ Me H MeCO

5-157 CF ₃ H CF ₃ Me H EtCO

5-158 CF ₃ H CF ₃ Me H n-PrCO

5-159 CF ₃ H CF ₃ Me H cyclo-PrCO

5-160 CF ₃ H CF ₃ Me H cyclo-PrCH ₂ CO

5-161 CF ₃ H CF ₃ Me H CF ₃ CH ₂ CO

5-162 CF ₃ H CF ₃ Me H CH ₃ SCH ₂ CO

5-163 CF ₃ H CF ₃ Me H CH ₃ SOCH ₂ CO

5-164 CF ₃ H CF ₃ Me H CH ₃ S0 ₂ CH ₂ CO

5-165 CF ₃ H CF ₃ Me H CH ₃ OCH ₂ CH ₂ CO

5-166 CF ₃ H CF ₃ Me H CH ₃ OCH(Me)CH ₂ CO

5-167 CF ₃ H CF ₃ Me H EtNHCO

5-168 CF ₃ H CF ₃ Me H tert-BuOC(=0)

5-169 CF ₃ H CF ₃ H H H

5-170 CF ₃ H CF ₃ H H MeCO

5-171 CF ₃ H CF ₃ H H EtCO

5-172 CF ₃ H CF ₃ H H n-PrCO

5-173 CF ₃ H CF ₃ H H cyclo-PrCO

5-174 CF ₃ H CF ₃ H H cyclo-PrCH ₂ CO

5-175 CF ₃ H CF ₃ H H CF ₃ CH ₂ CO

5-176 CF ₃ H CF ₃ H H CH ₃ SCH ₂ CO

5-177 CF ₃ H CF ₃ H H CH ₃ SOCH ₂ CO

5-178 CF ₃ H CF ₃ H H CH ₃ S0 ₂ CH ₂ CO

5-179 CF ₃ H CF ₃ H H CH ₃ OCH ₂ CH ₂ CO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

5-180 CF ₃ H CF ₃ H H CH ₃ OCH(Me)CH ₂ CO

5-181 CF ₃ H CF ₃ H H EtNHCO

5-182 CF ₃ H CF ₃ H H tert-BuOC(=0)

5-183 CI CI CF ₃ CF ₃ H H

5-184 CI CI CF ₃ CF ₃ H MeCO

5-185 CI CI CF ₃ CF ₃ H EtCO

5-186 CI CI CF ₃ CF ₃ H cyclo-PrCO

5-187 CI CI CF ₃ CF ₃ H CH ₃ SCH ₂ CO

5-188 CI CI CF ₃ CF ₃ H CF ₃ CH ₂ CO

5-189 CI CI CF ₃ CF ₃ H EtNHCO

5-190 CI CI CF ₃ CF ₃ H tert-BuOC(=0)

5-191 CI H CF ₃ CF ₃ H H

5-192 CI H CF ₃ CF ₃ H MeCO

5-193 CI H CF ₃ CF ₃ H EtCO

5-194 CI H CF ₃ CF ₃ H cyclo-PrCO

5-195 CI H CF ₃ CF ₃ H CH ₃ SCH ₂ CO

5-196 CI H CF ₃ CF ₃ H CF ₃ CH ₂ CO

5-197 CI H CF ₃ CF ₃ H EtNHCO

5-198 CI H CF ₃ CF ₃ H tert-BuOC(=0)

5-199 F H CF ₃ CF ₃ H H

5-200 F H CF ₃ CF ₃ H MeCO

5-201 F H CF ₃ CF ₃ H EtCO

5-202 F H CF ₃ CF ₃ H cyclo-PrCO

5-203 F H CF ₃ CF ₃ H CH ₃ SCH ₂ CO

5-204 F H CF ₃ CF ₃ H CF ₃ CH ₂ CO

5-205 F H CF ₃ CF ₃ H EtNHCO

5-206 F H CF ₃ CF ₃ H tert-BuOC(=0)

5-207 H F CF ₃ CF ₃ H H

5-208 H F CF ₃ CF ₃ H MeCO

5-209 H F CF ₃ CF ₃ H EtCO

5-210 H F CF ₃ CF ₃ H cyclo-PrCO

5-211 H F CF ₃ CF ₃ H CH ₃ SCH ₂ CO

5-212 H F CF ₃ CF ₃ H CF ₃ CH ₂ CO

5-213 H F CF ₃ CF ₃ H EtNHCO

5-214 H F CF ₃ CF ₃ H tert-BuOC(=0) Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

5-215 CI H CI Br H H

5-216 CI H CI Br H MeCO

5-217 CI H CI Br H EtCO

5-218 CI H CI Br H n-PrCO

5-219 CI H CI Br H cyclo-PrCO

5-220 CI H CI Br H cyclo-PrCH ₂ CO

5-221 CI H CI Br H CF ₃ CH ₂ CO

5-222 CI H CI Br H CH ₃ SCH ₂ CO

5-223 CI H CI Br H CH ₃ SOCH ₂ CO

5-224 CI H CI Br H CH ₃ S0 ₂ CH ₂ CO

5-225 CI H CI Br H CH ₃ OCH ₂ CH ₂ CO

5-226 CI H CI Br H CH ₃ OCH(Me)CH ₂ CO

5-227 CI H CI Br H EtNHCO

5-228 CI H CI Br H tert-BuOC(=0)

5-229 CI CI CI Br H H

5-230 CI CI CI Br H MeCO

5-231 CI CI CI Br H EtCO

5-232 CI CI CI Br H n-PrCO

5-233 CI CI CI Br H cyclo-PrCO

5-234 CI CI CI Br H cyclo-PrCH ₂ CO

5-235 CI CI CI Br H CF ₃ CH ₂ CO

5-236 CI CI CI Br H CH ₃ SCH ₂ CO

5-237 CI CI CI Br H CH ₃ SOCH ₂ CO

5-238 CI CI CI Br H CH ₃ S0 ₂ CH ₂ CO

5-239 CI CI CI Br H CH ₃ OCH ₂ CH ₂ CO

5-240 CI CI CI Br H CH ₃ OCH(Me)CH ₂ CO

5-241 CI CI CI Br H EtNHCO

5-242 CI CI CI Br H tert-BuOC(=0)

5-243 CF ₃ H H Br H H

5-244 CF ₃ H H Br H MeCO

5-245 CF ₃ H H Br H EtCO

5-246 CF ₃ H H Br H n-PrCO

5-247 CF ₃ H H Br H cyclo-PrCO

5-248 CF ₃ H H Br H cyclo-PrCH ₂ CO

5-249 CF ₃ H H Br H CF ₃ CH ₂ CO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

5-250 CF ₃ H H Br H CH ₃ SCH ₂ CO

5-251 CF ₃ H H Br H CH ₃ SOCH ₂ CO

5-252 CF ₃ H H Br H CH ₃ S0 ₂ CH ₂ CO

5-253 CF ₃ H H Br H CH ₃ OCH ₂ CH ₂ CO

5-254 CF ₃ H H Br H CH ₃ OCH(Me)CH ₂ CO

5-255 CF ₃ H H Br H EtNHCO

5-256 CF ₃ H H Br H tert-BuOC(=0)

5-257 CF ₃ H CF ₃ Br H H

5-258 CF ₃ H CF ₃ Br H MeCO

5-259 CF ₃ H CF ₃ Br H EtCO

5-260 CF ₃ H CF ₃ Br H n-PrCO

5-261 CF ₃ H CF ₃ Br H cyclo-PrCO

5-262 CF ₃ H CF ₃ Br H cyclo-PrCH ₂ CO

5-263 CF ₃ H CF ₃ Br H CF ₃ CH ₂ CO

5-264 CF ₃ H CF ₃ Br H CH ₃ SCH ₂ CO

5-265 CF ₃ H CF ₃ Br H CH ₃ SOCH ₂ CO

5-266 CF ₃ H CF ₃ Br H CH ₃ S0 ₂ CH ₂ CO

5-267 CF ₃ H CF ₃ Br H CH ₃ OCH ₂ CH ₂ CO

5-268 CF ₃ H CF ₃ Br H CH ₃ OCH(Me)CH ₂ CO

5-269 CF ₃ H CF ₃ Br H EtNHCO

5-270 CF ₃ H CF ₃ Br H tert-BuOC(=0)

5-271 Br H Br CF ₃ H H

5-272 Br H Br CF ₃ H MeCO

5-273 Br H Br CF ₃ H EtCO

5-274 Br H Br CF ₃ H n-PrCO

5-275 Br H Br CF ₃ H cyclo-PrCO

5-276 Br H Br CF ₃ H cyclo-PrCH ₂ CO

5-277 Br H Br CF ₃ H CF ₃ CH ₂ CO

5-278 Br H Br CF ₃ H CH ₃ SCH ₂ CO

5-279 Br H Br CF ₃ H CH ₃ SOCH ₂ CO

5-280 Br H Br CF ₃ H CH ₃ S0 ₂ CH ₂ CO

5-281 Br H Br CF ₃ H CH ₃ OCH ₂ CH ₂ CO

5-282 Br H Br CF ₃ H CH ₃ OCH(Me)CH ₂ CO

5-283 Br H Br CF ₃ H EtNHCO

5-284 Br H Br CF ₃ H tert-BuOC(=0) Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

5-285 Br H Br CI H H

5-286 Br H Br CI H MeCO

5-287 Br H Br CI H EtCO

5-288 Br H Br CI H n-PrCO

5-289 Br H Br CI H cyclo-PrCO

5-290 Br H Br CI H cyclo-PrCH ₂ CO

5-291 Br H Br CI H CF3CH2CO

5-292 Br H Br CI H CH3SCH2CO

5-293 Br H Br CI H CH3SOCH2CO

5-294 Br H Br CI H CH3SO2CH2CO

5-295 Br H Br CI H CH3OCH2CH2CO

5-296 Br H Br CI H CH ₃ OCH(Me)CH ₂ CO

5-297 Br H Br CI H EtNHCO

5-298 Br H Br CI H tert-BuOC(=0)

5-299 Br H Br Br H H

5-300 Br H Br Br H MeCO

5-301 Br H Br Br H EtCO

5-302 Br H Br Br H n-PrCO

5-303 Br H Br Br H cyclo-PrCO

5-304 Br H Br Br H cyclo-PrCH ₂ CO

5-305 Br H Br Br H CF3CH2CO

5-306 Br H Br Br H CH3SCH2CO

5-307 Br H Br Br H CH3SOCH2CO

5-308 Br H Br Br H CH3SO2CH2CO

5-309 Br H Br Br H CH3OCH2CH2CO

5-310 Br H Br Br H CH ₃ OCH(Me)CH ₂ CO

5-311 Br H Br Br H EtNHCO

5-312 Br H Br Br H tert-BuOC(=0)

5-313 Br H Br Me H H

5-314 Br H Br Me H MeCO

5-315 Br H Br Me H EtCO

5-316 Br H Br Me H n-PrCO

5-317 Br H Br Me H cyclo-PrCO

5-318 Br H Br Me H cyclo-PrCH ₂ CO

5-319 Br H Br Me H CF3CH2CO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

5-354 CI H CI H Me tert-BuOC(=0)

5-355 Br H Br H Me H

5-356 Br H Br H Me MeCO

5-357 Br H Br H Me EtCO

5-358 Br H Br H Me n-PrCO

5-359 Br H Br H Me cyclo-PrCO

5-360 Br H Br H Me cyclo-PrCH ₂ CO

5-361 Br H Br H Me CF3CH2CO

5-362 Br H Br H Me CH3SCH2CO

5-363 Br H Br H Me CH3SOCH2CO

5-364 Br H Br H Me CH3SO2CH2CO

5-365 Br H Br H Me CH3OCH2CH2CO

5-366 Br H Br H Me CH ₃ OCH(Me)CH ₂ CO

5-367 Br H Br H Me EtNHCO

5-368 Br H Br H Me tert-BuOC(=0)

5-369 CI CI CI H Me H

5-370 CI CI CI H Me MeCO

5-370-a CI CI CI H Me MeCO

5-371 CI CI CI H Me EtCO

5-371-a CI CI CI H Me EtCO

5-371-b CI CI CI H Me EtCO

5-372 CI CI CI H Me n-PrCO

5-373 CI CI CI H Me cyclo-PrCO

5-373-a CI CI CI H Me cyclo-PrCO

5-374 CI CI CI H Me cyclo-PrCH ₂ CO

5-374-a CI CI CI H Me cyclo-PrCH ₂ CO

5-375 CI CI CI H Me CF3CH2CO

5-375-a CI CI CI H Me CF3CH2CO

5-376 CI CI CI H Me CH3SCH2CO

5-377 CI CI CI H Me CH3SOCH2CO

5-378 CI CI CI H Me CH3SO2CH2CO

5-379 CI CI CI H Me CH3OCH2CH2CO

5-379-a CI CI CI H Me CH3OCH2CH2CO

5-380 CI CI CI H Me CH ₃ OCH(Me)CH ₂ CO

5-381 CI CI CI H Me EtNHCO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

5-382 CI CI CI H Me tert-BuOC(=0)

5-383 CF ₃ H H H Me H

5-384 CF ₃ H H H Me MeCO

5-385 CF ₃ H H H Me EtCO

5-386 CF ₃ H H H Me n-PrCO

5-387 CF ₃ H H H Me cyclo-PrCO

5-388 CF ₃ H H H Me cyclo-PrCH ₂ CO

5-389 CF ₃ H H H Me CF ₃ CH ₂ CO

5-390 CF ₃ H H H Me CH ₃ SCH ₂ CO

5-391 CF ₃ H H H Me CH ₃ SOCH ₂ CO

5-392 CF ₃ H H H Me CH ₃ S0 ₂ CH ₂ CO

5-393 CF ₃ H H H Me CH ₃ OCH ₂ CH ₂ CO

5-394 CF ₃ H H H Me CH ₃ OCH(Me)CH ₂ CO

5-395 CF ₃ H H H Me EtNHCO

5-396 CF ₃ H H H Me tert-BuOC(=0)

5-397 CF ₃ H CF ₃ H Me H

5-398 CF ₃ H CF ₃ H Me MeCO

5-399 CF ₃ H CF ₃ H Me MeCO

5-400 CF ₃ H CF ₃ H Me EtCO

5-401 CF ₃ H CF ₃ H Me EtCO

5-402 CF ₃ H CF ₃ H Me EtCO

5-403 CF ₃ H CF ₃ H Me n-PrCO

5-404 CF ₃ H CF ₃ H Me cyclo-PrCO

5-405 CF ₃ H CF ₃ H Me cyclo-PrCO

5-406 CF ₃ H CF ₃ H Me cyclo-PrCH ₂ CO

5-407 CF ₃ H CF ₃ H Me cyclo-PrCH ₂ CO

5-408 CF ₃ H CF ₃ H Me CF ₃ CH ₂ CO

5-409 CF ₃ H CF ₃ H Me CF ₃ CH ₂ CO

5-410 CF ₃ H CF ₃ H Me CH ₃ SCH ₂ CO

5-411 CF ₃ H CF ₃ H Me CH ₃ SOCH ₂ CO

5-412 CF ₃ H CF ₃ H Me CH ₃ S0 ₂ CH ₂ CO

5-413 CF ₃ H CF ₃ H Me CH ₃ OCH ₂ CH ₂ CO

5-414 CF ₃ H CF ₃ H Me CH ₃ OCH ₂ CH ₂ CO

5-415 CF ₃ H CF ₃ H Me CH ₃ OCH(Me)CH ₂ CO

5-416 CF ₃ H CF ₃ H Me EtNHCO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

5-417 CF ₃ H CF ₃ H Me tert-BuOC(=0)

5-418 CI CI CF ₃ H Me H

5-419 CI CI CF ₃ H Me MeCO

5-420 CI CI CF ₃ H Me EtCO

5-421 CI CI CF ₃ H Me cyclo-PrCO

5-422 CI CI CF ₃ H Me CH ₃ SCH ₂ CO

5-423 CI CI CF ₃ H Me CF ₃ CH ₂ CO

5-424 CI CI CF ₃ H Me EtNHCO

5-425 CI CI CF ₃ H Me tert-BuOC(=0)

5-426 CI H CF ₃ H Me H

5-427 CI H CF ₃ H Me MeCO

5-428 CI H CF ₃ H Me EtCO

5-429 CI H CF ₃ H Me cyclo-PrCO

5-430 CI H CF ₃ H Me CH ₃ SCH ₂ CO

5-431 CI H CF ₃ H Me CF ₃ CH ₂ CO

5-432 CI H CF ₃ H Me EtNHCO

5-433 CI H CF ₃ H Me tert-BuOC(=0)

5-434 F H CF ₃ H Me H

5-435 F H CF ₃ H Me MeCO

5-436 F H CF ₃ H Me EtCO

5-437 F H CF ₃ H Me cyclo-PrCO

5-438 F H CF ₃ H Me CH ₃ SCH ₂ CO

5-439 F H CF ₃ H Me CF ₃ CH ₂ CO

5-440 F H CF ₃ H Me EtNHCO

5-441 F H CF ₃ H Me tert-BuOC(=0)

5-442 H F CF ₃ H Me H

5-443 H F CF ₃ H Me MeCO

5-444 H F CF ₃ H Me EtCO

5-445 H F CF ₃ H Me cyclo-PrCO

5-446 H F CF ₃ H Me CH ₃ SCH ₂ CO

5-447 H F CF ₃ H Me CF ₃ CH ₂ CO

5-448 H F CF ₃ H Me EtNHCO

5-449 H F CF ₃ H Me tert-BuOC(=0)

5-450 OCF ₃ H H CF ₃ H EtCO

5-451 SCF ₃ H H CF ₃ H EtCO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

5-452 SOCF ₃ H H CF ₃ H EtCO

5-453 SO2CF3 H H CF ₃ H EtCO

Wherein, X ¹ , X ⁵ , Y ¹ , Y ² , Y ⁴ and R ³ represent hydrogen.

Table 6

Compound No. X ² X ³ X ⁴ R ⁴ m

6-24 Br H Br CH ₃ S0 ₂ CH ₂ CO ¹

6-25 Br H Br CH ₃ OCH ₂ CH ₂ CO ¹

6-26 Br H Br CH ₃ OCH(Me)CH ₂ CO ¹

6-27 Br H Br EtNHCO ¹

6-28 Br H Br tert-BuOC(=0) ¹

6-29 CI CI CI H ¹

6-30 CI CI CI MeCO ¹

6-31 CI CI CI EtCO ¹

6-32 CI CI CI n-PrCO ¹

6-33 CI CI CI cyclo-PrCO ¹

6-34 CI CI CI cyclo-PrCH ₂ CO ¹

6-35 CI CI CI CF ₃ CH ₂ CO ¹

6-36 CI CI CI CH ₃ SCH ₂ CO ¹

6-37 CI CI CI CH ₃ SOCH ₂ CO ¹

6-38 CI CI CI CH ₃ S0 ₂ CH ₂ CO ¹

6-39 CI CI CI CH ₃ OCH ₂ CH ₂ CO ¹

6-40 CI CI CI CH ₃ OCH(Me)CH ₂ CO ¹

6-41 CI CI CI EtNHCO ¹

6-42 CI CI CI tert-BuOC(=0) ¹

6-43 CF ₃ H H H ¹

6-44 CF ₃ H H MeCO ¹

6-45 CF ₃ H H EtCO ¹

6-46 CF ₃ H H n-PrCO ¹

6-47 CF ₃ H H cyclo-PrCO ¹

6-48 CF ₃ H H cyclo-PrCH ₂ CO ¹

6-49 CF ₃ H H CF ₃ CH ₂ CO ¹

6-50 CF ₃ H H CH ₃ SCH ₂ CO ¹

6-51 CF ₃ H H CH ₃ SOCH ₂ CO ¹

6-52 CF ₃ H H CH ₃ S0 ₂ CH ₂ CO ¹

6-53 CF ₃ H H CH ₃ OCH ₂ CH ₂ CO ¹

6-54 CF ₃ H H CH ₃ OCH(Me)CH ₂ CO ¹

6-55 CF ₃ H H EtNHCO ¹

6-56 CF ₃ H H tert-BuOC(=0) ¹

6-57 CF ₃ H CF ₃ H ¹

6-58 CF ₃ H CF ₃ MeCO ¹ Compound No. X ² X ³ X ⁴ R ⁴ m

6-59 CF ₃ H CF ₃ EtCO ¹

6-60 CF ₃ H CF ₃ n-PrCO ¹

6-61 CF ₃ H CF ₃ cyclo-PrCO ¹

6-62 CF ₃ H CF ₃ cyclo-PrCH ₂ CO ¹

6-63 CF ₃ H CF ₃ CF ₃ CH ₂ CO ¹

6-64 CF ₃ H CF ₃ CH ₃ SCH ₂ CO ¹

6-65 CF ₃ H CF ₃ CH ₃ SOCH ₂ CO ¹

6-66 CF ₃ H CF ₃ CH ₃ S0 ₂ CH ₂ CO ¹

6-67 CF ₃ H CF ₃ CH ₃ OCH ₂ CH ₂ CO ¹

6-68 CF ₃ H CF ₃ CH ₃ OCH(Me)CH ₂ CO ¹

6-69 CF ₃ H CF ₃ EtNHCO ¹

6-70 CF ₃ H CF ₃ tert-BuOC(=0) ¹

6-71 CI CI CF ₃ H ¹

6-72 CI CI CF ₃ MeCO ¹

6-73 CI CI CF ₃ EtCO ¹

6-74 CI CI CF ₃ cyclo-PrCO ¹

6-75 CI CI CF ₃ CH ₃ SCH ₂ CO ¹

6-76 CI CI CF ₃ CF ₃ CH ₂ CO ¹

6-77 CI CI CF ₃ EtNHCO ¹

6-78 CI CI CF ₃ tert-BuOC(=0) ¹

6-79 CI H CF ₃ H ¹

6-80 CI H CF ₃ MeCO ¹

6-81 CI H CF ₃ EtCO ¹

6-82 CI H CF ₃ cyclo-PrCO ¹

6-83 CI H CF ₃ CH ₃ SCH ₂ CO ¹

6-84 CI H CF ₃ CF ₃ CH ₂ CO ¹

6-85 CI H CF ₃ EtNHCO ¹

6-86 CI H CF ₃ tert-BuOC(=0) ¹

6-87 F H CF ₃ H ¹

6-88 F H CF ₃ MeCO ¹

6-89 F H CF ₃ EtCO ¹

6-90 F H CF ₃ cyclo-PrCO ¹

6-91 F H CF ₃ CH ₃ SCH ₂ CO ¹

6-92 F H CF ₃ CF ₃ CH ₂ CO ¹

6-93 F H CF ₃ EtNHCO ¹ Compound No. X ² X ³ X ⁴ R ⁴ m

6-94 F H CF ₃ tert-BuOC(=0) ¹

6-95 H F CF ₃ H ¹

6-96 H F CF ₃ MeCO ¹

6-97 H F CF ₃ EtCO ¹

6-98 H F CF ₃ cyclo-PrCO ¹

6-99 H F CF ₃ CH ₃ SCH ₂ CO ¹

6-100 H F CF ₃ CF ₃ CH ₂ CO ¹

6-101 H F CF ₃ EtNHCO ¹

6-102 H F CF ₃ tert-BuOC(=0) ¹

6-103 CI H CI H 2

6-104 CI H CI MeCO 2

6-105 CI H CI EtCO 2

6-106 CI H CI n-PrCO 2

6-107 CI H CI cyclo-PrCO 2

6-108 CI H CI cyclo-PrCH ₂ CO 2

6-109 CI H CI CF ₃ CH ₂ CO 2

6-110 CI H CI CH ₃ SCH ₂ CO 2

6-111 CI H CI CH ₃ SOCH ₂ CO 2

6-112 CI H CI CH ₃ S0 ₂ CH ₂ CO 2

6-113 CI H CI CH ₃ OCH ₂ CH ₂ CO 2

6-114 CI H CI CH ₃ OCH(Me)CH ₂ CO 2

6-115 CI H CI EtNHCO 2

6-116 CI H CI tert-BuOC(=0) 2

6-117 Br H Br H 2

6-118 Br H Br MeCO 2

6-119 Br H Br EtCO 2

6-120 Br H Br n-PrCO 2

6-121 Br H Br cyclo-PrCO 2

6-122 Br H Br cyclo-PrCH ₂ CO 2

6-123 Br H Br CF ₃ CH ₂ CO 2

6-124 Br H Br CH ₃ SCH ₂ CO 2

6-125 Br H Br CH ₃ SOCH ₂ CO 2

6-126 Br H Br CH ₃ S0 ₂ CH ₂ CO 2

6-127 Br H Br CH ₃ OCH ₂ CH ₂ CO 2

6-128 Br H Br CH ₃ OCH(Me)CH ₂ CO 2 Compound No. X ² X ³ X ⁴ R ⁴ m

6-129 Br H Br EtNHCO 2

6-130 Br H Br tert-BuOC(=0) 2

6-131 CI CI CI H 2

6-132 CI CI CI MeCO 2

6-133 CI CI CI EtCO 2

6-134 CI CI CI n-PrCO 2

6-135 CI CI CI cyclo-PrCO 2

6-136 CI CI CI cyclo-PrCH ₂ CO 2

6-137 CI CI CI CF ₃ CH ₂ CO 2

6-138 CI CI CI CH ₃ SCH ₂ CO 2

6-139 CI CI CI CH ₃ SOCH ₂ CO 2

6-140 CI CI CI CH ₃ S0 ₂ CH ₂ CO 2

6-141 CI CI CI CH ₃ OCH ₂ CH ₂ CO 2

6-142 CI CI CI CH ₃ OCH(Me)CH ₂ CO 2

6-143 CI CI CI EtNHCO 2

6-144 CI CI CI tert-BuOC(=0) 2

6-145 CF ₃ H H H 2

6-146 CF ₃ H H MeCO 2

6-147 CF ₃ H H EtCO 2

6-148 CF ₃ H H n-PrCO 2

6-149 CF ₃ H H cyclo-PrCO 2

6-150 CF ₃ H H cyclo-PrCH ₂ CO 2

6-151 CF ₃ H H CF ₃ CH ₂ CO 2

6-152 CF ₃ H H CH ₃ SCH ₂ CO 2

6-153 CF ₃ H H CH ₃ SOCH ₂ CO 2

6-154 CF ₃ H H CH ₃ S0 ₂ CH ₂ CO 2

6-155 CF ₃ H H CH ₃ OCH ₂ CH ₂ CO 2

6-156 CF ₃ H H CH ₃ OCH(Me)CH ₂ CO 2

6-157 CF ₃ H H EtNHCO 2

6-158 CF ₃ H H tert-BuOC(=0) 2

6-159 CF ₃ H CF ₃ H 2

6-160 CF ₃ H CF ₃ MeCO 2

6-161 CF ₃ H CF ₃ EtCO 2

6-162 CF ₃ H CF ₃ n-PrCO 2

6-163 CF ₃ H CF ₃ cyclo-PrCO 2 Compound No. X ² X ³ X ⁴ R ⁴ m

6-164 CF ₃ H CF ₃ cyclo-PrCH ₂ CO 2

6-165 CF ₃ H CF ₃ CF ₃ CH ₂ CO 2

6-166 CF ₃ H CF ₃ CH ₃ SCH ₂ CO 2

6-167 CF ₃ H CF ₃ CH ₃ SOCH ₂ CO 2

6-168 CF ₃ H CF ₃ CH ₃ S0 ₂ CH ₂ CO 2

6-169 CF ₃ H CF ₃ CH ₃ OCH ₂ CH ₂ CO 2

6-170 CF ₃ H CF ₃ CH ₃ OCH(Me)CH ₂ CO 2

6-171 CF ₃ H CF ₃ EtNHCO 2

6-172 CF ₃ H CF ₃ tert-BuOC(=0) 2

6-173 CI CI CF ₃ H 2

6-174 CI CI CF ₃ MeCO 2

6-175 CI CI CF ₃ EtCO 2

6-176 CI CI CF ₃ cyclo-PrCO 2

6-177 CI CI CF ₃ CH ₃ SCH ₂ CO 2

6-178 CI CI CF ₃ CF ₃ CH ₂ CO 2

6-179 CI CI CF ₃ EtNHCO 2

6-180 CI CI CF ₃ tert-BuOC(=0) 2

6-181 CI H CF ₃ H 2

6-182 CI H CF ₃ MeCO 2

6-183 CI H CF ₃ EtCO 2

6-184 CI H CF ₃ cyclo-PrCO 2

6-185 CI H CF ₃ CH ₃ SCH ₂ CO 2

6-186 CI H CF ₃ CF ₃ CH ₂ CO 2

6-187 CI H CF ₃ EtNHCO 2

6-188 CI H CF ₃ tert-BuOC(=0) 2

6-189 F H CF ₃ H 2

6-190 F H CF ₃ MeCO 2

6-191 F H CF ₃ EtCO 2

6-192 F H CF ₃ cyclo-PrCO 2

6-193 F H CF ₃ CH ₃ SCH ₂ CO 2

6-194 F H CF ₃ CF ₃ CH ₂ CO 2

6-195 F H CF ₃ EtNHCO 2

6-196 F H CF ₃ tert-BuOC(=0) 2

6-197 H F CF ₃ H 2

6-198 H F CF ₃ MeCO 2

Wherein, X ¹ , X ⁵ , Y ¹ , Y ² , Y ⁴ , R ² and R ³ represent hydrogen.

Table 7

Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

7-17 CI CI CI CF ₃ H EtCO

7-18 CI CI CI CF ₃ H n-PrCO

7-19 CI CI CI CF ₃ H cyclo-PrCO

7-20 CI CI CI CF ₃ H cyclo-PrCH ₂ CO

7-21 CI CI CI CF ₃ H CF ₃ CH ₂ CO

7-22 CI CI CI CF ₃ H CH ₃ SCH ₂ CO

7-23 CI CI CI CF ₃ H CH ₃ SOCH ₂ CO

7-24 CI CI CI CF ₃ H CH ₃ S0 ₂ CH ₂ CO

7-25 CI CI CI CF ₃ H CH ₃ OCH ₂ CH ₂ CO

7-26 CI CI CI CF ₃ H CH ₃ OCH(Me)CH ₂ CO

7-27 CI CI CI CF ₃ H EtNHCO

7-28 CI CI CI CF ₃ H tert-BuOC(=0)

7-29 CI CI CI CI H H

7-30 CI CI CI CI H MeCO

7-31 CI CI CI CI H EtCO

7-32 CI CI CI CI H n-PrCO

7-33 CI CI CI CI H cyclo-PrCO

7-34 CI CI CI CI H cyclo-PrCH ₂ CO

7-35 CI CI CI CI H CF ₃ CH ₂ CO

7-36 CI CI CI CI H CH ₃ SCH ₂ CO

7-37 CI CI CI CI H CH ₃ SOCH ₂ CO

7-38 CI CI CI CI H CH ₃ S0 ₂ CH ₂ CO

7-39 CI CI CI CI H CH ₃ OCH ₂ CH ₂ CO

7-40 CI CI CI CI H CH ₃ OCH(Me)CH ₂ CO

7-41 CI CI CI CI H EtNHCO

7-42 CI CI CI CI H tert-BuOC(=0)

7-43 CI CI CI Me H H

7-44 CI CI CI Me H MeCO

7-45 CI CI CI Me H EtCO

7-46 CI CI CI Me H n-PrCO

7-47 CI CI CI Me H cyclo-PrCO

7-48 CI CI CI Me H cyclo-PrCH ₂ CO

7-49 CI CI CI Me H CF ₃ CH ₂ CO

7-50 CI CI CI Me H CH ₃ SCH ₂ CO

7-51 CI CI CI Me H CH ₃ SOCH ₂ CO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

7-52 CI CI CI Me H CH ₃ S0 ₂ CH ₂ CO

7-53 CI CI CI Me H CH ₃ OCH ₂ CH ₂ CO

7-54 CI CI CI Me H CH ₃ OCH(Me)CH ₂ CO

7-55 CI CI CI Me H EtNHCO

7-56 CI CI CI Me H tert-BuOC(=0)

7-57 CI CI CI H H H

7-58 CI CI CI H H MeCO

7-59 CI CI CI H H EtCO

7-60 CI CI CI H H n-PrCO

7-61 CI CI CI H H cyclo-PrCO

7-62 CI CI CI H H cyclo-PrCH ₂ CO

7-63 CI CI CI H H CF ₃ CH ₂ CO

7-64 CI CI CI H H CH ₃ SCH ₂ CO

7-65 CI CI CI H H CH ₃ SOCH ₂ CO

7-66 CI CI CI H H CH ₃ S0 ₂ CH ₂ CO

7-67 CI CI CI H H CH ₃ OCH ₂ CH ₂ CO

7-68 CI CI CI H H CH ₃ OCH(Me)CH ₂ CO

7-69 CI CI CI H H EtNHCO

7-70 CI CI CI H H tert-BuOC(=0)

7-71 CF ₃ H H CF ₃ H H

7-72 CF ₃ H H CF ₃ H MeCO

7-73 CF ₃ H H CF ₃ H EtCO

7-74 CF ₃ H H CF ₃ H n-PrCO

7-75 CF ₃ H H CF ₃ H cyclo-PrCO

7-76 CF ₃ H H CF ₃ H cyclo-PrCH ₂ CO

7-77 CF ₃ H H CF ₃ H CF ₃ CH ₂ CO

7-78 CF ₃ H H CF ₃ H CH ₃ SCH ₂ CO

7-79 CF ₃ H H CF ₃ H CH ₃ SOCH ₂ CO

7-80 CF ₃ H H CF ₃ H CH ₃ S0 ₂ CH ₂ CO

7-81 CF ₃ H H CF ₃ H CH ₃ OCH ₂ CH ₂ CO

7-82 CF ₃ H H CF ₃ H CH ₃ OCH(Me)CH ₂ CO

7-83 CF ₃ H H CF ₃ H EtNHCO

7-84 CF ₃ H H CF ₃ H tert-BuOC(=0)

7-85 CF ₃ H H CI H H

7-86 CF ₃ H H CI H MeCO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

7-87 CF ₃ H H CI H EtCO

7-88 CF ₃ H H CI H n-PrCO

7-89 CF ₃ H H CI H cyclo-PrCO

7-90 CF ₃ H H CI H cyclo-PrCH ₂ CO

7-91 CF ₃ H H CI H CF ₃ CH ₂ CO

7-92 CF ₃ H H CI H CH ₃ SCH ₂ CO

7-93 CF ₃ H H CI H CH ₃ SOCH ₂ CO

7-94 CF ₃ H H CI H CH ₃ S0 ₂ CH ₂ CO

7-95 CF ₃ H H CI H CH ₃ OCH ₂ CH ₂ CO

7-96 CF ₃ H H CI H CH ₃ OCH(Me)CH ₂ CO

7-97 CF ₃ H H CI H EtNHCO

7-98 CF ₃ H H CI H tert-BuOC(=0)

7-99 CF ₃ H H Me H H

7-100 CF ₃ H H Me H MeCO

7-101 CF ₃ H H Me H EtCO

7-102 CF ₃ H H Me H n-PrCO

7-103 CF ₃ H H Me H cyclo-PrCO

7-104 CF ₃ H H Me H cyclo-PrCH ₂ CO

7-105 CF ₃ H H Me H CF ₃ CH ₂ CO

7-106 CF ₃ H H Me H CH ₃ SCH ₂ CO

7-107 CF ₃ H H Me H CH ₃ SOCH ₂ CO

7-108 CF ₃ H H Me H CH ₃ S0 ₂ CH ₂ CO

7-109 CF ₃ H H Me H CH ₃ OCH ₂ CH ₂ CO

7-110 CF ₃ H H Me H CH ₃ OCH(Me)CH ₂ CO

7-111 CF ₃ H H Me H EtNHCO

7-112 CF ₃ H H Me H tert-BuOC(=0)

7-113 CF ₃ H H H H H

7-114 CF ₃ H H H H MeCO

7-115 CF ₃ H H H H EtCO

7-116 CF ₃ H H H H n-PrCO

7-117 CF ₃ H H H H cyclo-PrCO

7-118 CF ₃ H H H H cyclo-PrCH ₂ CO

7-119 CF ₃ H H H H CF ₃ CH ₂ CO

7-120 CF ₃ H H H H CH ₃ SCH ₂ CO

7-121 CF ₃ H H H H CH ₃ SOCH ₂ CO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

7-122 CF ₃ H H H H CH ₃ S0 ₂ CH ₂ CO

7-123 CF ₃ H H H H CH ₃ OCH ₂ CH ₂ CO

7-124 CF ₃ H H H H CH ₃ OCH(Me)CH ₂ CO

7-125 CF ₃ H H H H EtNHCO

7-126 CF ₃ H H H H tert-BuOC(=0)

7-127 CF ₃ H CF ₃ CF ₃ H H

7-128 CF ₃ H CF ₃ CF ₃ H MeCO

7-129 CF ₃ H CF ₃ CF ₃ H EtCO

7-130 CF ₃ H CF ₃ CF ₃ H n-PrCO

7-131 CF ₃ H CF ₃ CF ₃ H cyclo-PrCO

7-132 CF ₃ H CF ₃ CF ₃ H cyclo-PrCH ₂ CO

7-133 CF ₃ H CF ₃ CF ₃ H CF ₃ CH ₂ CO

7-134 CF ₃ H CF ₃ CF ₃ H CH ₃ SCH ₂ CO

7-135 CF ₃ H CF ₃ CF ₃ H CH ₃ SOCH ₂ CO

7-136 CF ₃ H CF ₃ CF ₃ H CH ₃ S0 ₂ CH ₂ CO

7-137 CF ₃ H CF ₃ CF ₃ H CH ₃ OCH ₂ CH ₂ CO

7-138 CF ₃ H CF ₃ CF ₃ H CH ₃ OCH(Me)CH ₂ CO

7-139 CF ₃ H CF ₃ CF ₃ H EtNHCO

7-140 CF ₃ H CF ₃ CF ₃ H tert-BuOC(=0)

7-141 CF ₃ H CF ₃ CI H H

7-142 CF ₃ H CF ₃ CI H MeCO

7-143 CF ₃ H CF ₃ CI H EtCO

7-144 CF ₃ H CF ₃ CI H n-PrCO

7-145 CF ₃ H CF ₃ CI H cyclo-PrCO

7-146 CF ₃ H CF ₃ CI H cyclo-PrCH ₂ CO

7-147 CF ₃ H CF ₃ CI H CF ₃ CH ₂ CO

7-148 CF ₃ H CF ₃ CI H CH ₃ SCH ₂ CO

7-149 CF ₃ H CF ₃ CI H CH ₃ SOCH ₂ CO

7-150 CF ₃ H CF ₃ CI H CH ₃ S0 ₂ CH ₂ CO

7-151 CF ₃ H CF ₃ CI H CH ₃ OCH ₂ CH ₂ CO

7-152 CF ₃ H CF ₃ CI H CH ₃ OCH(Me)CH ₂ CO

7-153 CF ₃ H CF ₃ CI H EtNHCO

7-154 CF ₃ H CF ₃ CI H tert-BuOC(=0)

7-155 CF ₃ H CF ₃ Me H H

7-156 CF ₃ H CF ₃ Me H MeCO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

7-157 CF ₃ H CF ₃ Me H EtCO

7-158 CF ₃ H CF ₃ Me H n-PrCO

7-159 CF ₃ H CF ₃ Me H cyclo-PrCO

7-160 CF ₃ H CF ₃ Me H cyclo-PrCH ₂ CO

7-161 CF ₃ H CF ₃ Me H CF ₃ CH ₂ CO

7-162 CF ₃ H CF ₃ Me H CH ₃ SCH ₂ CO

7-163 CF ₃ H CF ₃ Me H CH ₃ SOCH ₂ CO

7-164 CF ₃ H CF ₃ Me H CH ₃ S0 ₂ CH ₂ CO

7-165 CF ₃ H CF ₃ Me H CH ₃ OCH ₂ CH ₂ CO

7-166 CF ₃ H CF ₃ Me H CH ₃ OCH(Me)CH ₂ CO

7-167 CF ₃ H CF ₃ Me H EtNHCO

7-168 CF ₃ H CF ₃ Me H tert-BuOC(=0)

7-169 CF ₃ H CF ₃ H H H

7-170 CF ₃ H CF ₃ H H MeCO

7-171 CF ₃ H CF ₃ H H EtCO

7-172 CF ₃ H CF ₃ H H n-PrCO

7-173 CF ₃ H CF ₃ H H cyclo-PrCO

7-174 CF ₃ H CF ₃ H H cyclo-PrCH ₂ CO

7-175 CF ₃ H CF ₃ H H CF ₃ CH ₂ CO

7-176 CF ₃ H CF ₃ H H CH ₃ SCH ₂ CO

7-177 CF ₃ H CF ₃ H H CH ₃ SOCH ₂ CO

7-178 CF ₃ H CF ₃ H H CH ₃ S0 ₂ CH ₂ CO

7-179 CF ₃ H CF ₃ H H CH ₃ OCH ₂ CH ₂ CO

7-180 CF ₃ H CF ₃ H H CH ₃ OCH(Me)CH ₂ CO

7-181 CF ₃ H CF ₃ H H EtNHCO

7-182 CF ₃ H CF ₃ H H tert-BuOC(=0)

7-183 CI CI CF ₃ CF ₃ H H

7-184 CI CI CF ₃ CF ₃ H MeCO

7-185 CI CI CF ₃ CF ₃ H EtCO

7-186 CI CI CF ₃ CF ₃ H cyclo-PrCO

7-187 CI CI CF ₃ CF ₃ H CH ₃ SCH ₂ CO

7-188 CI CI CF ₃ CF ₃ H CF ₃ CH ₂ CO

7-189 CI CI CF ₃ CF ₃ H EtNHCO

7-190 CI CI CF ₃ CF ₃ H tert-BuOC(=0)

7-191 CI H CF ₃ CF ₃ H H Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

7-192 CI H CF ₃ CF ₃ H MeCO

7-193 CI H CF ₃ CF ₃ H EtCO

7-194 CI H CF ₃ CF ₃ H cyclo-PrCO

7-195 CI H CF ₃ CF ₃ H CH ₃ SCH ₂ CO

7-196 CI H CF ₃ CF ₃ H CF ₃ CH ₂ CO

7-197 CI H CF ₃ CF ₃ H EtNHCO

7-198 CI H CF ₃ CF ₃ H tert-BuOC(=0)

7-199 F H CF ₃ CF ₃ H H

7-200 F H CF ₃ CF ₃ H MeCO

7-201 F H CF ₃ CF ₃ H EtCO

7-202 F H CF ₃ CF ₃ H cyclo-PrCO

7-203 F H CF ₃ CF ₃ H CH ₃ SCH ₂ CO

7-204 F H CF ₃ CF ₃ H CF ₃ CH ₂ CO

7-205 F H CF ₃ CF ₃ H EtNHCO

7-206 F H CF ₃ CF ₃ H tert-BuOC(=0)

7-207 H F CF ₃ CF ₃ H H

7-208 H F CF ₃ CF ₃ H MeCO

7-209 H F CF ₃ CF ₃ H EtCO

7-210 H F CF ₃ CF ₃ H cyclo-PrCO

7-211 H F CF ₃ CF ₃ H CH ₃ SCH ₂ CO

7-212 H F CF ₃ CF ₃ H CF ₃ CH ₂ CO

7-213 H F CF ₃ CF ₃ H EtNHCO

7-214 H F CF ₃ CF ₃ H tert-BuOC(=0)

7-215 CI H CI Br H H

7-216 CI H CI Br H MeCO

7-217 CI H CI Br H EtCO

7-218 CI H CI Br H n-PrCO

7-219 CI H CI Br H cyclo-PrCO

7-220 CI H CI Br H cyclo-PrCH ₂ CO

7-221 CI H CI Br H CF ₃ CH ₂ CO

7-222 CI H CI Br H CH ₃ SCH ₂ CO

7-223 CI H CI Br H CH ₃ SOCH ₂ CO

7-224 CI H CI Br H CH ₃ S0 ₂ CH ₂ CO

7-225 CI H CI Br H CH ₃ OCH ₂ CH ₂ CO

7-226 CI H CI Br H CH ₃ OCH(Me)CH ₂ CO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

7-227 CI H CI Br H EtNHCO

7-228 CI H CI Br H tert-BuOC(=0)

7-229 CI CI CI Br H H

7-230 CI CI CI Br H MeCO

7-231 CI CI CI Br H EtCO

7-232 CI CI CI Br H n-PrCO

7-233 CI CI CI Br H cyclo-PrCO

7-234 CI CI CI Br H cyclo-PrCH ₂ CO

7-235 CI CI CI Br H CF ₃ CH ₂ CO

7-236 CI CI CI Br H CH ₃ SCH ₂ CO

7-237 CI CI CI Br H CH ₃ SOCH ₂ CO

7-238 CI CI CI Br H CH ₃ S0 ₂ CH ₂ CO

7-239 CI CI CI Br H CH ₃ OCH ₂ CH ₂ CO

7-240 CI CI CI Br H CH ₃ OCH(Me)CH ₂ CO

7-241 CI CI CI Br H EtNHCO

7-242 CI CI CI Br H tert-BuOC(=0)

7-243 CF ₃ H H Br H H

7-244 CF ₃ H H Br H MeCO

7-245 CF ₃ H H Br H EtCO

7-246 CF ₃ H H Br H n-PrCO

7-247 CF ₃ H H Br H cyclo-PrCO

7-248 CF ₃ H H Br H cyclo-PrCH ₂ CO

7-249 CF ₃ H H Br H CF ₃ CH ₂ CO

7-250 CF ₃ H H Br H CH ₃ SCH ₂ CO

7-251 CF ₃ H H Br H CH ₃ SOCH ₂ CO

7-252 CF ₃ H H Br H CH ₃ S0 ₂ CH ₂ CO

7-253 CF ₃ H H Br H CH ₃ OCH ₂ CH ₂ CO

7-254 CF ₃ H H Br H CH ₃ OCH(Me)CH ₂ CO

7-255 CF ₃ H H Br H EtNHCO

7-256 CF ₃ H H Br H tert-BuOC(=0)

7-257 CF ₃ H CF ₃ Br H H

7-258 CF ₃ H CF ₃ Br H MeCO

7-259 CF ₃ H CF ₃ Br H EtCO

7-260 CF ₃ H CF ₃ Br H n-PrCO

7-261 CF ₃ H CF ₃ Br H cyclo-PrCO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

7-262 CF ₃ H CF ₃ Br H cyclo-PrCH ₂ CO

7-263 CF ₃ H CF ₃ Br H CF ₃ CH ₂ CO

7-264 CF ₃ H CF ₃ Br H CH ₃ SCH ₂ CO

7-265 CF ₃ H CF ₃ Br H CH ₃ SOCH ₂ CO

7-266 CF ₃ H CF ₃ Br H CH ₃ S0 ₂ CH ₂ CO

7-267 CF ₃ H CF ₃ Br H CH ₃ OCH ₂ CH ₂ CO

7-268 CF ₃ H CF ₃ Br H CH ₃ OCH(Me)CH ₂ CO

7-269 CF ₃ H CF ₃ Br H EtNHCO

7-270 CF ₃ H CF ₃ Br H tert-BuOC(=0)

7-271 Br H Br CF ₃ H H

7-272 Br H Br CF ₃ H MeCO

7-273 Br H Br CF ₃ H EtCO

7-274 Br H Br CF ₃ H n-PrCO

7-275 Br H Br CF ₃ H cyclo-PrCO

7-276 Br H Br CF ₃ H cyclo-PrCH ₂ CO

7-277 Br H Br CF ₃ H CF ₃ CH ₂ CO

7-278 Br H Br CF ₃ H CH ₃ SCH ₂ CO

7-279 Br H Br CF ₃ H CH ₃ SOCH ₂ CO

7-280 Br H Br CF ₃ H CH ₃ S0 ₂ CH ₂ CO

7-281 Br H Br CF ₃ H CH ₃ OCH ₂ CH ₂ CO

7-282 Br H Br CF ₃ H CH ₃ OCH(Me)CH ₂ CO

7-283 Br H Br CF ₃ H EtNHCO

7-284 Br H Br CF ₃ H tert-BuOC(=0)

7-285 Br H Br CI H H

7-286 Br H Br CI H MeCO

7-287 Br H Br CI H EtCO

7-288 Br H Br CI H n-PrCO

7-289 Br H Br CI H cyclo-PrCO

7-290 Br H Br CI H cyclo-PrCH ₂ CO

7-291 Br H Br CI H CF ₃ CH ₂ CO

7-292 Br H Br CI H CH ₃ SCH ₂ CO

7-293 Br H Br CI H CH ₃ SOCH ₂ CO

7-294 Br H Br CI H CH ₃ S0 ₂ CH ₂ CO

7-295 Br H Br CI H CH ₃ OCH ₂ CH ₂ CO

7-296 Br H Br CI H CH ₃ OCH(Me)CH ₂ CO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

7-297 Br H Br CI H EtNHCO

7-298 Br H Br CI H tert-BuOC(=0)

7-299 Br H Br Br H H

7-300 Br H Br Br H MeCO

7-301 Br H Br Br H EtCO

7-302 Br H Br Br H n-PrCO

7-303 Br H Br Br H cyclo-PrCO

7-304 Br H Br Br H cyclo-PrCH ₂ CO

7-305 Br H Br Br H CF3CH2CO

7-306 Br H Br Br H CH3SCH2CO

7-307 Br H Br Br H CH3SOCH2CO

7-308 Br H Br Br H CH3SO2CH2CO

7-309 Br H Br Br H CH3OCH2CH2CO

7-310 Br H Br Br H CH ₃ OCH(Me)CH ₂ CO

7-311 Br H Br Br H EtNHCO

7-312 Br H Br Br H tert-BuOC(=0)

7-313 Br H Br Me H H

7-314 Br H Br Me H MeCO

7-315 Br H Br Me H EtCO

7-316 Br H Br Me H n-PrCO

7-317 Br H Br Me H cyclo-PrCO

7-318 Br H Br Me H cyclo-PrCH ₂ CO

7-319 Br H Br Me H CF3CH2CO

7-320 Br H Br Me H CH3SCH2CO

7-321 Br H Br Me H CH3SOCH2CO

7-322 Br H Br Me H CH3SO2CH2CO

7-323 Br H Br Me H CH3OCH2CH2CO

7-324 Br H Br Me H CH ₃ OCH(Me)CH ₂ CO

7-325 Br H Br Me H EtNHCO

7-326 Br H Br Me H tert-BuOC(=0)

7-327 Br H Br H H H

7-328 Br H Br H H MeCO

7-329 Br H Br H H EtCO

7-330 Br H Br H H n-PrCO

7-331 Br H Br H H cyclo-PrCO

Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

7-366 Br H Br H Me CH ₃ OCH(Me)CH ₂ CO

7-367 Br H Br H Me EtNHCO

7-368 Br H Br H Me tert-BuOC(=0)

7-369 CI CI CI H Me H

7-370 CI CI CI H Me MeCO

7-370-a CI CI CI H Me MeCO

7-371 CI CI CI H Me EtCO

7-371-a CI CI CI H Me EtCO

7-371-b CI CI CI H Me EtCO

7-372 CI CI CI H Me n-PrCO

7-373 CI CI CI H Me cyclo-PrCO

7-373-a CI CI CI H Me cyclo-PrCO

7-374 CI CI CI H Me cyclo-PrCH ₂ CO

7-374-a CI CI CI H Me cyclo-PrCH ₂ CO

7-375 CI CI CI H Me CF ₃ CH ₂ CO

7-375-a CI CI CI H Me CF ₃ CH ₂ CO

7-376 CI CI CI H Me CH ₃ SCH ₂ CO

7-377 CI CI CI H Me CH ₃ SOCH ₂ CO

7-378 CI CI CI H Me CH ₃ S0 ₂ CH ₂ CO

7-379 CI CI CI H Me CH ₃ OCH ₂ CH ₂ CO

7-379-a CI CI CI H Me CH ₃ OCH ₂ CH ₂ CO

7-380 CI CI CI H Me CH ₃ OCH(Me)CH ₂ CO

7-381 CI CI CI H Me EtNHCO

7-382 CI CI CI H Me tert-BuOC(=0)

7-383 CF ₃ H H H Me H

7-384 CF ₃ H H H Me MeCO

7-385 CF ₃ H H H Me EtCO

7-386 CF ₃ H H H Me n-PrCO

7-387 CF ₃ H H H Me cyclo-PrCO

7-388 CF ₃ H H H Me cyclo-PrCH ₂ CO

7-389 CF ₃ H H H Me CF ₃ CH ₂ CO

7-390 CF ₃ H H H Me CH ₃ SCH ₂ CO

7-391 CF ₃ H H H Me CH ₃ SOCH ₂ CO

7-392 CF ₃ H H H Me CH ₃ S0 ₂ CH ₂ CO

7-393 CF ₃ H H H Me CH ₃ OCH ₂ CH ₂ CO Compound No. X ² X ³ X ⁴ Y ³ R ¹ R ⁴

7-394 CF ₃ H H H Me CH ₃ OCH(Me)CH ₂ CO

7-395 CF ₃ H H H Me EtNHCO

7-396 CF ₃ H H H Me tert-BuOC(=0)

7-397 CF ₃ H CF ₃ H Me H

7-398 CF ₃ H CF ₃ H Me MeCO

7-398-a CF ₃ H CF ₃ H Me MeCO

7-399 CF ₃ H CF ₃ H Me EtCO

7-399-a CF ₃ H CF ₃ H Me EtCO

7-399-b CF ₃ H CF ₃ H Me EtCO

7-400 CF ₃ H CF ₃ H Me n-PrCO

7-401 CF ₃ H CF ₃ H Me cyclo-PrCO

7-401-a CF ₃ H CF ₃ H Me cyclo-PrCO

7-402 CF ₃ H CF ₃ H Me cyclo-PrCH ₂ CO

7-402-a CF ₃ H CF ₃ H Me cyclo-PrCH ₂ CO

7-403 CF ₃ H CF ₃ H Me CF ₃ CH ₂ CO

7-403-a CF ₃ H CF ₃ H Me CF ₃ CH ₂ CO

7-404 CF ₃ H CF ₃ H Me CH ₃ SCH ₂ CO

7-405 CF ₃ H CF ₃ H Me CH ₃ SOCH ₂ CO

7-406 CF ₃ H CF ₃ H Me CH ₃ S0 ₂ CH ₂ CO

7-407 CF ₃ H CF ₃ H Me CH ₃ OCH ₂ CH ₂ CO

7-407-a CF ₃ H CF ₃ H Me CH ₃ OCH ₂ CH ₂ CO

7-408 CF ₃ H CF ₃ H Me CH ₃ OCH(Me)CH ₂ CO

7-409 CF ₃ H CF ₃ H Me EtNHCO

7-410 CF ₃ H CF ₃ H Me tert-BuOC(=0)

7-411 CI CI CF ₃ H Me H

7-412 CI CI CF ₃ H Me MeCO

7-413 CI CI CF ₃ H Me EtCO

7-414 CI CI CF ₃ H Me cyclo-PrCO

7-415 CI CI CF ₃ H Me CH ₃ SCH ₂ CO

7-416 CI CI CF ₃ H Me CF ₃ CH ₂ CO

7-417 CI CI CF ₃ H Me EtNHCO

7-418 CI CI CF ₃ H Me tert-BuOC(=0)

7-419 CI H CF ₃ H Me H

7-420 CI H CF ₃ H Me MeCO

7-421 CI H CF ₃ H Me EtCO

Wherein, X ¹ , X ⁵ , Y ¹ , Y ² , Y ⁴ and R ³ represent hydrogen. Table 8

Compound No. X ² X ³ X ⁴ R ⁴ m

8-35 CI CI CI CF ₃ CH ₂ CO ¹

8-36 CI CI CI CH ₃ SCH ₂ CO ¹

8-37 CI CI CI CH ₃ SOCH ₂ CO ¹

8-38 CI CI CI CH ₃ S0 ₂ CH ₂ CO ¹

8-39 CI CI CI CH ₃ OCH ₂ CH ₂ CO ¹

8-40 CI CI CI CH ₃ OCH(Me)CH ₂ CO ¹

8-41 CI CI CI EtNHCO ¹

8-42 CI CI CI tert-BuOC(=0) ¹

8-43 CF ₃ H H H ¹

8-44 CF ₃ H H MeCO ¹

8-45 CF ₃ H H EtCO ¹

8-46 CF ₃ H H n-PrCO ¹

8-47 CF ₃ H H cyclo-PrCO ¹

8-48 CF ₃ H H cyclo-PrCH ₂ CO ¹

8-49 CF ₃ H H CF ₃ CH ₂ CO ¹

8-50 CF ₃ H H CH ₃ SCH ₂ CO ¹

8-51 CF ₃ H H CH ₃ SOCH ₂ CO ¹

8-52 CF ₃ H H CH ₃ S0 ₂ CH ₂ CO ¹

8-53 CF ₃ H H CH ₃ OCH ₂ CH ₂ CO ¹

8-54 CF ₃ H H CH ₃ OCH(Me)CH ₂ CO ¹

8-55 CF ₃ H H EtNHCO ¹

8-56 CF ₃ H H tert-BuOC(=0) ¹

8-57 CF ₃ H CF ₃ H ¹

8-58 CF ₃ H CF ₃ MeCO ¹

8-59 CF ₃ H CF ₃ EtCO ¹

8-60 CF ₃ H CF ₃ n-PrCO ¹

8-61 CF ₃ H CF ₃ cyclo-PrCO ¹

8-62 CF ₃ H CF ₃ cyclo-PrCH ₂ CO ¹

8-63 CF ₃ H CF ₃ CF ₃ CH ₂ CO ¹

8-64 CF ₃ H CF ₃ CH ₃ SCH ₂ CO ¹

8-65 CF ₃ H CF ₃ CH ₃ SOCH ₂ CO ¹

8-66 CF ₃ H CF ₃ CH ₃ S0 ₂ CH ₂ CO ¹

8-67 CF ₃ H CF ₃ CH ₃ OCH ₂ CH ₂ CO ¹

8-68 CF ₃ H CF ₃ CH ₃ OCH(Me)CH ₂ CO ¹

8-69 CF ₃ H CF ₃ EtNHCO ¹ Compound No. X ² X ³ X ⁴ R ⁴ m

8-70 CF ₃ H CF ₃ tert-BuOC(=0) ¹

8-71 CI CI CF ₃ H ¹

8-72 CI CI CF ₃ MeCO ¹

8-73 CI CI CF ₃ EtCO ¹

8-74 CI CI CF ₃ cyclo-PrCO ¹

8-75 CI CI CF ₃ CH ₃ SCH ₂ CO ¹

8-76 CI CI CF ₃ CF ₃ CH ₂ CO ¹

8-77 CI CI CF ₃ EtNHCO ¹

8-78 CI CI CF ₃ tert-BuOC(=0) ¹

8-79 CI H CF ₃ H ¹

8-80 CI H CF ₃ MeCO ¹

8-81 CI H CF ₃ EtCO ¹

8-82 CI H CF ₃ cyclo-PrCO ¹

8-83 CI H CF ₃ CH ₃ SCH ₂ CO ¹

8-84 CI H CF ₃ CF ₃ CH ₂ CO ¹

8-85 CI H CF ₃ EtNHCO ¹

8-86 CI H CF ₃ tert-BuOC(=0) ¹

8-87 F H CF ₃ H ¹

8-88 F H CF ₃ MeCO ¹

8-89 F H CF ₃ EtCO ¹

8-90 F H CF ₃ cyclo-PrCO ¹

8-91 F H CF ₃ CH ₃ SCH ₂ CO ¹

8-92 F H CF ₃ CF ₃ CH ₂ CO ¹

8-93 F H CF ₃ EtNHCO ¹

8-94 F H CF ₃ tert-BuOC(=0) ¹

8-95 H F CF ₃ H ¹

8-96 H F CF ₃ MeCO ¹

8-97 H F CF ₃ EtCO ¹

8-98 H F CF ₃ cyclo-PrCO ¹

8-99 H F CF ₃ CH ₃ SCH ₂ CO ¹

8-100 H F CF ₃ CF ₃ CH ₂ CO ¹

8-101 H F CF ₃ EtNHCO ¹

8-102 H F CF ₃ tert-BuOC(=0) ¹

8-103 CI H CI H 2

8-104 CI H CI MeCO 2 Compound No. X ² X ³ X ⁴ R ⁴ m

8-140 CI CI CI CH ₃ S0 ₂ CH ₂ CO 2

8-141 CI CI CI CH ₃ OCH ₂ CH ₂ CO 2

8-142 CI CI CI CH ₃ OCH(Me)CH ₂ CO 2

8-143 CI CI CI EtNHCO 2

8-144 CI CI CI tert-BuOC(=0) 2

8-145 CF ₃ H H H 2

8-146 CF ₃ H H MeCO 2

8-147 CF ₃ H H EtCO 2

8-148 CF ₃ H H n-PrCO 2

8-149 CF ₃ H H cyclo-PrCO 2

8-150 CF ₃ H H cyclo-PrCH ₂ CO 2

8-151 CF ₃ H H CF ₃ CH ₂ CO 2

8-152 CF ₃ H H CH ₃ SCH ₂ CO 2

8-153 CF ₃ H H CH ₃ SOCH ₂ CO 2

8-154 CF ₃ H H CH ₃ S0 ₂ CH ₂ CO 2

8-155 CF ₃ H H CH ₃ OCH ₂ CH ₂ CO 2

8-156 CF ₃ H H CH ₃ OCH(Me)CH ₂ CO 2

8-157 CF ₃ H H EtNHCO 2

8-158 CF ₃ H H tert-BuOC(=0) 2

8-159 CF ₃ H CF ₃ H 2

8-160 CF ₃ H CF ₃ MeCO 2

8-161 CF ₃ H CF ₃ EtCO 2

8-162 CF ₃ H CF ₃ n-PrCO 2

8-163 CF ₃ H CF ₃ cyclo-PrCO 2

8-164 CF ₃ H CF ₃ cyclo-PrCH ₂ CO 2

8-165 CF ₃ H CF ₃ CF ₃ CH ₂ CO 2

8-166 CF ₃ H CF ₃ CH ₃ SCH ₂ CO 2

8-167 CF ₃ H CF ₃ CH ₃ SOCH ₂ CO 2

8-168 CF ₃ H CF ₃ CH ₃ S0 ₂ CH ₂ CO 2

8-169 CF ₃ H CF ₃ CH ₃ OCH ₂ CH ₂ CO 2

8-170 CF ₃ H CF ₃ CH ₃ OCH(Me)CH ₂ CO 2

8-171 CF ₃ H CF ₃ EtNHCO 2

8-172 CF ₃ H CF ₃ tert-BuOC(=0) 2

8-173 CI CI CF ₃ H 2

8-174 CI CI CF ₃ MeCO 2

Wherein, X ¹ , X ⁵ , Y ¹ , Y ² and Y ⁴ represent hydrogen.

Table 9

Compound No. X ² X ³ X ⁴ Y ³

9-1 CI H CI CF ₃

9-2 CI H CI CI

9-3 CI H CI Br

9-4 CI H CI Me

9-5 CI H CI H

9-6 Br H Br CF ₃

9-7 Br H Br CI

9-8 Br H Br Br

9-9 Br H Br Me

9-10 Br H Br H

9-11 CI CI CI CF ₃

9-12 CI CI CI CI

9-13 CI CI CI Me

9-14 CI CI CI H

9-15 CF ₃ H H CF ₃

9-16 CF ₃ H H CI

9-17 CF ₃ H H Me

9-18 CF ₃ H H H

9-19 CF ₃ H CF ₃ CF ₃

9-20 CF ₃ H CF ₃ CI

9-21 CF ₃ H CF ₃ Me

9-22 CF ₃ H CF ₃ H

9-23 CI CI CF ₃ CF ₃

9-24 CI H CF ₃ CF ₃

9-25 F H CF ₃ CF ₃

9-26 H F CF ₃ CF ₃

9-27 OCF ₃ H H CF ₃

Wherein, X ¹ , X ⁵ , Y ¹ , Y ² and Y ⁴ represent hydrogen.

Table 10

Compound No. X ² X ³ X ⁴ Y ³

10-1 CI H CI CF ₃

10-2 CI H CI CI

10-3 CI H CI Br

10-4 CI H CI Me

10-5 CI H CI H

10-6 Br H Br CF ₃

10-7 Br H Br CI

10-8 Br H Br Br

10-9 Br H Br Me

10-10 Br H Br H

10-11 CI CI CI CF ₃

10-12 CI CI CI CI

10-13 CI CI CI Me

10-14 CI CI CI H

10-15 CF ₃ H H CF ₃

10-16 CF ₃ H H CI

10-17 CF ₃ H H Me

10-18 CF ₃ H H H

10-19 CF ₃ H CF ₃ CF ₃

10-20 CF ₃ H CF ₃ CI

10-21 CF ₃ H CF ₃ Me

10-22 CF ₃ H CF ₃ H

Wherein, X ¹ , X ⁵ , Y ¹ , Y ² and Y ⁴ represent hydrogen.

Table 11

Compound No. X ² X ³ X ⁴ Y ³

11-1 CI H CI CF ₃

11-2 CI H CI CI

11-3 CI H CI Br

11-4 CI H CI Me

11-5 CI H CI H

11-6 Br H Br CF ₃

11-7 Br H Br CI

11-8 Br H Br Br

11-9 Br H Br Me

11-10 Br H Br H

11-11 CI CI CI CF ₃

11-12 CI CI CI CI

11-13 CI CI CI Me

11-14 CI CI CI H

11-15 CF ₃ H H CF ₃ Compound No. X ² X ³ X ⁴ Y ³

11-16 CF ₃ H H CI

11-17 CF ₃ H H Me

11-18 CF ₃ H H H

11-19 CF ₃ H CF ₃ CF ₃

11-20 CF ₃ H CF ₃ CI

11-21 CF ₃ H CF ₃ Me

11-22 CF ₃ H CF ₃ H

11-23 CI CI CF ₃ CF ₃

11-24 CI H CF ₃ CF ₃

11-25 F H CF ₃ CF ₃

11-26 H F CF ₃ CF ₃

11-27 OCF ₃ H H CF ₃

11-28 SCF ₃ H H CF ₃

11-29 SOCF ₃ H H CF ₃

11-30 S0 ₂ CF ₃ H H CF ₃

(NMR Table)

Table 12

Compound

IH-NMR

No.

IH-NMR (CDC13) δ: 1.13-1.16 (3H, m), 2.18-2.23 (3H, m), 3.77-3.81 (IH, m), 4.12-

1-17 4.15 (IH, m), 4.50 (2H, d), 5.20 (2H, d), 5.73 (IH, br s), 6.67 (IH, d), 6.77 (IH, d), 7.48

(IH, d), 7.59 (2H, s).

IH-NMR (CDC13) δ: 7.59 (2H, s), 7.48 (IH, d), 6.77 (IH, d), 6.68 (IH, d), 5.88 (IH, s),

1-19

5.20 (2H, d), 4.52 (2H, d), 1.30 (IH, m), 0.98 (2H, m), 0.73 (2H, m).

IH-NMR (CDC13) δ: 1.14-1.16 (3H, m), 2.17-2.27 (2H, m), 4.09-4.74 (4H, m), 5.80

3-17

(IH, br s), 7.22-7.65 (5H, m).

IH-NMR (CDC13) δ: 7.64 (3H, m), 7.33 (2H, d), 5.97 (IH, s), 4.56 (4H, m), 1.34 (IH,

3-19

m), 1.02-0.97 (2H, m), 0.80-0.75 (2H, m).

IH-NMR (CDC13) δ: 7.47 (2H, m), 7.21-7.00 (2H, m), 6.34 (IH, m), 4.58-4.05 (3H, m),

3-20

3.60 (IH, m), 2.01 (2H, m), 0.84-0.66 (IH, m), 0.50-0.39 (2H, m), 0.00 (2H, m).

IH-NMR (CDC13) δ: 1.11-1.18 (3H, m), 2.16-2.24 (2H, m), 4.07-4.40 (4H, m), 5.82

3-73

(IH, br s), 7.21-7.92 (7H, m).

IH-NMR (CDC13) δ: 7.63 (2H, s), 7.48-7.33 (3H, m), 7.14 (IH, m), 6.66 (IH, d), 4.68

3-382

(IH, m), 4.24 (IH, m), 4.15 (IH, m), 1.43 (12H, m). Compound

IH-NMR

No.

IH-NMR (CDC13) δ: 1.04-1.07 (3H, m), 1.64-1.74 (IH, m), 2.08-2.18 (2H, m), 2.42-

4-3 2.46 (IH, m), 2.69-2.85 (2H, m), 4.10-4.27 (IH, m), 4.46-4.57 (IH, m), 5.27-5.30 (IH, m), 6.04-6.07 (IH, m), 6.80-7.01 (2H, m), 7.10-7.23 (IH, m), 7.36-7.44 (3H, m).

IH-NMR (CDC13) δ: 7.68-7.47 (4H, m), 7.29 (IH, m), 5.87 (IH, m), 4.67-4.23 (4H, m),

5-17

2.28-2.18 (2H, m), 1.18-1.11 (3H, t).

lH-NMR (CDC13) e: 7.73-7.18 (5H, m), 6.11 (IH, m), 4.40 (4H, m), 1.43-1.31 (lH, m),

5-19

0.95 (2H, m), 0.78 (2H, m).

IH-NMR (CDC13) δ: 7.66-7.55 (3H, m), 7.37-7.19 (2H, m), 6.38 (IH, m), 4.64-4.55

5-20 (2H, m), 4.38 (IH, m), 4.23 (IH, m), 2.19-2.13 (2H, m), 0.97-0.85 (IH, m), 0.63-0.55

(2H, m), 0.17 (2H, m).

IH-NMR (CDC13) δ: 7.60 (2H, m), 7.32 (4H, m), 6.11 (IH, m), 5.18-5.08 (IH, m), 4.56

5-374-a (IH, m), 4.23 (I H, m), 2.15 (2H, m), 1.46 (3H, m), 0.96 (IH, m), 0.61 (2H, m), 0.19

(2H, m).

IH-NMR (CDC13) δ: 7.60 (2H, m), 7.46-7.39 (2H, m), 7.27 (2H, m), 6.46 (IH, m),

5-375-a

5.12-5.03 (IH, m), 4.59 (IH, m), 4.28 (IH, m), 3.01 (2H, m), 1.51-1.43 (3H, m).

IH-NMR (CDC13) δ: 1.20 (3H, t), 1.81-1.84 (IH, m), 2.26 (2H, q), 2.62-2.65 (IH, m),

6-3 2.89-2.97 (2H, m), 4.24 (IH, d), 4.60 (IH, d), 5.50-5.56 (2H, m), 7.13-7.16 (IH, m),

7.28-7.32 (2H, m), 7.46 (2H, s), 7.52 (IH, s).

IH-NMR (CDC13) δ: 1.14 (3H, t), 2.21 (2H, q), 3.63-3.66 (IH, m), 3.88-3.93 (IH, m),

7-17 3.98-4.00 (IH, m), 4.40-4.43 (3H, m), 5.74 (IH, br s), 6.70-6.71 (IH, m), 6.86 (IH, s),

7.27-7.30 (IH, m), 7.64 (2H, s).

1H-NMR (CDC13) δ: 7.64 (2H, m), 7.10 (lH, m), 6.75 (lH, m), 6.54 (lH, m), 6.11 (IH,

7-19 m), 5.53 (IH, m), 4.35 (2H, m), 4.22-4.14 (IH, m), 3.76 (2H, m), 1.37 (IH, m), 0.92

(2H, m), 0.79 (2H, m).

IH-NMR (CDC13) δ: 7.65 (2H, s), 6.84 (IH, d), 6.64 (IH, d), 6.33 (IH, s), 4.88 (IH, s),

7-20 4.45 (2H, d), 4.09 (IH, s), 3.77 (2H, m), 2.17 (2H, m), 0.89 (IH, m), 0.62-0.56 (2H, m),

0.16 (2H, m).

IH-NMR (CDC13) δ: 3.21 (2H, d), 3.65-3.68 (IH, m), 3.87-3.91 (IH, m), 4.48 (2H, d),

7-21

6.74 (IH, d), 6.86 (IH, s), 6.95 (IH, br s), 7.27-7.29 (IH, m), 7.64 (2H, s).

IH-NMR (CDC13) δ: 1.14 (3H, t), 2.19-2.22 (2H, m), 3.69-3.72 (IH, m), 3.96-4.00 (2H,

7-73 m), 4.45 (2H, d), 5.70 (IH, br s), 6.75 (IH, d), 6.86 (IH, s), 7.35 (IH, d), 7.56-7.59 (IH, m), 7.69 (IH, d), 7.80 (IH, d.), 7.91 (IH, s).

IH-NMR (CDC13) δ: 7.63 (2H, m), 7.33-7.02 (3H, m), 6.55 (IH, m), 5.74 (IH, m), 5.14

7-371-a

(IH, m), 5.00 (IH, m), 3.73 (2H, m), 2.23-2.13 (2H, m), 1.46-1.40 (3H, d), 1.13 (3H, t). Compound

1H-NMR

No.

1H-NMR (CDC13) δ: 7.63 (2H, m), 7.08 (2H, m), 6.59 (2H, m), 5.84 (1H, m), 5.01 -4.94

7-373-a (1H, m), 4.70 (1H, m), 3.92-3.54 (2H, m), 1.49-1.42 (3H, m), 1.36-1.27 (1H, m), 0.92

(2H, m), 0.71 (2H, m).

1H-NMR (CDC13) δ: 4.33 (1H, dd), 4.67 (1 H, dd), 7.31-7.39 (2H, m), 7.62 (2H, d),

9-11

7.83-7.86 (1H, m).

10-11 1H-NMR (CDC13) δ: 4.36 (1H, d), 4.73 (1H, d), 7.57-7.64 (4H, m), 7.92 (1H, d).

1H-NMR (CDC13) δ: 3.77 (1H, dd), 3.93 (1H, dd), 4.47 (1H, br s), 6.78-6.81 (1H, m),

11-11

6.92 (1H, d), 7.58-7.61 (3H, m).

Unless other methods are mentioned specifically, the sample solution preparation was prepared as follows.

Solvent: 3 parts by weight of dimethyl formamide Emulsifier: 1 part by weight of polyoxyethylene alkyl phenyl ether

To prepare a suitable concoction including the active compound, 1 part by weight of the active compound was mixed with the above amount of the solvent containing the above amount of the emulsifier, and the resulting mixture was diluted with water to predetermined concentrations.

Biological Test Example 1 : Test on Tetranychus urticae (Test method)

50 to 100 of adult Tetranychus urticae were inoculated to leaves at 2-leaf stage of Egyptian bean planted in pots of 6 cm in diameter, to which, 1 day later, the above prepared water diluted solution of the active compound at the predetermined concentration was sufficiently sprayed with a spray gun. After the compounds were sprayed, the pots were left in a greenhouse and the acaricidal ratio was calculated seven days later. 100% acaricidal ratio means death of all the mites, while 0%> acaricidal ratio means none of the mites were dead.

(Test result)

In the Biological Test Example 1 above, the following compounds as a representative example showed a pest-controlling efficacy of 100% acaricidal ratio at 100 ppm of an effective component concentration: Compound No. 1-17, 1-19, 5-17, 5-19, 5-20, 5-374-a and 5-375-a. Biological Test Example 2: Test on Aulacophora femoralis (Test method)

Leaves of cucumbers were immersed in the water-diluted solution containing the active compound at the predetermined concentration which was prepared above and, after the solution was air- dried, the resultant leaves were put onto sterilized black soil in a plastic cup, into which five of the 2nd- instar larvae of Aulacophora femoralis were then released. The cup was covered with a lid and maintained in a temperature controlled room at 25°C having humidity of 50 to 60%. Seven days later, the number of dead larvae was counted to calculate the pesticidal ratio. 100%) pesticidal ratio means death of all the larvae, while 0%> pesticidal ratio means no dead larvae. (Test result)

In the Biological Test Example 2 above, the following compounds as a representative example showed a pest-controlling efficacy of 100% pesticidal ratio at 100 ppm of an effective component concentration: Compound No. 1-17, 1-19, 3-17, 3-19, 3-20, 5-17, 5-19, 5-20, 5-374-a, 5-375-a and 7-19.

Biological test example 3 : Test on larvae of Spodoptera litura (a method using artificial feeds) (Test method)

Powdery artificial feeds (trade name: SILK MATE, manufactured by Nihon Nosan Kogyo, Japan, 2.3 g) were added to a plastic cup (diameter: 7.5 cm, height: 4 cm) to achieve a certain thickness. Water-diluted liquid (5 mL) of the active compound prepared above having predetermined concentration was evenly poured thereto and allowed to stand until the feeds are solidified. Five of the 3rd-instar larvae of Spodoptera litura were released in each cup, and covered with a lid. The cups were put in a temperature controlled room at 25°C having humidity of 50 to 60%>, and the number of dead larvae after 7 days was determined to calculate the pesticidal ratio. 100%) pesticidal ratio means death of all the larvae, while 0%> pesticidal ratio means no dead larvae.

(Test result) In the Biological Test Example 3 above, the following compounds as a representative example showed a pest-controlling efficacy of 100% pesticidal ratio at 100 ppm of an effective component concentration: Compound No. 1-17, 1-19, 3-17, 3-19, 3-20, 4-3, 5-17, 5-19, 5-20, 5-374-a, 5-375-a, 6-3, 7-19 and 10-11.