DD241845A5 - INSECTICIDE COMPOSITION - Google Patents

Abstract

The invention relates to insecticidal compositions containing as active ingredient N-aryl-3-aryl-4,5-dihydro-1H-pyrazole-1-carboxamides including N-aryl-3-aryl-4,5-dihydro-1H-pyrazole-1 thiocarboxamides and N-aryl-3-aryl-4,5-dihydro-1H-pyrazole-1-iminocarboxamides which are disubstituted at the 4-position or monosubstituted at the 4-position. The new active ingredients are biologically particularly easily degradable.

Description

The invention relates to a novel insecticidal composition.

Characteristic of the known technical solutions:

The search for insecticides that have a combination of excellent insecticidal Virksamkeit and ira essentially no toxicity, is an ongoing process because aer knowledge of the possible toxicity of many known insecticides for animals and humans.

Certain pyrazoline derivatives have been disclosed as being "insecticidally effective."

DE-OS 2 304 584 discloses substituted pyrazoline compounds having biocidal activity in the 1,3- or 1,3,5-positions of the pyrazole ring. DE-OS 2 304 584 corresponds to US Pat. No. 3,991,083; 4 095 026 and 4 OlO 271.

U.S. Patent 4,156,007; 4,070,365 and 4,174,393 disclose substituted pyrazoline compounds having insecticidal activity in the 1,3 and 4 positions of the pyrazoline ring.

U.S. Patent Nos. 4,140,707 and 4,140,792 disclose in the 1,3,5-digit

tions of the pyrazoline ring, substituted pyrazoline compounds

-Z-

which have arthropodzide properties.

It is believed that currently known compounds are prone to photostability and biodegradability problems. These compounds tend to decompose faster than desired when applied to the outer plant parts due to exposure of the sunlight to these compounds. In addition, when known compounds are applied to the soil, they show poor biodegradability, resulting in an undesirable residue remaining in the soil.

Object of the invention:

It is therefore an object of the invention to provide novel insecticidal compositions whose active ingredients have improved lightfastness and biodegradability.

Explanation of the essence of the invention;

According to the invention, the novel insecticidal composition contains compounds of the formula I as active ingredient:

in which mean:

A unsubstituted or substituted aryl; B unsubstituted or substituted aryl; U 0, S or N-O;

I U * t

V is hydrogen, (C _x -C f -) - cycloalkyl, unsubstituiartes

4 or substituted aryl or R-Q;

Y. lower straight-chain or branched-chain, unsubstituted

substituted or substituted (C ₁ -C ₆ ) -alkyl, unsubstituted

substituted or substituted aryl

or X

a group of the formula --C - G in which X is 0, S or

NQ represents,

Z is hydrogen, (C ₂ -C, -) - "cycloalkyl, unsubstituted or substituted aryl or R"-Q; with the proviso that Z is not hydrogen, when Y is alkyl or aryl and Z is not methyl, when Y is methyl,

Q is hydrogen, halogen, cyano, nitro, OR ", R OR, CO ₂ R ¹ , NR ¹ COR ² , OR ⁴ OR ¹ , CR ¹ R ² R ³ , CONR ¹ R ² , NR ¹ R ² , N (COR ¹ ) COR ² , OSR ¹ , SR ¹ , SOR ¹ , SO ₂ R ¹ , NR ¹ SOR ² , R ⁴ SR ¹ , OR ⁴ SR ¹ , SR ⁴ SR ¹ , SNHSR ¹ , SNMSOgR ¹ , CONHSR ¹ , OCOR ¹ , R ¹ , .. C (SNR ¹ JR ² , COR ¹ , N ₃ , OSOgR ¹ , NR ¹ SO ₂ R ² , NR ¹ CSR ² , alkenyl (CR ³ = CR ² R ³ ), alkynyl (C = CR ¹ ), or aryl;

12-R, R and R independently of one another are hydrogen, halogen, cyano, nitro, hydroxy, an alkoxy group (OR) having up to four carbon atoms, an amino group (NH ₂ ), an alkylamino group (NHR) having up to six carbon atoms, a Dialkylamino group (NH ₂ ) having independently up to six carbon atoms in each alkyl moiety, a carboxy group (CO ₂ H), a carbalkoxy group (CO ₂ R) of up to six carbon atoms, an alkylcarbonyl group (COR) of up to six carbon atoms, an alkanoyloxy group) OCOR) having up to six carbon atoms, a carboxamide group (COMH ₂ , CONHR or CONR ₂ ) with independently up to six carbon atoms in each alkyl component, a carbamoyloxy group (OCONH, OCONHR or OCONR ₂ ) with independent

up to six carbon atoms in each alkyl moiety, a sulfhydryl, a sulfinyl group (-60R) of up to six carbon atoms, a sulfonyl group (-SO ₂ R) of up to six carbon atoms, a sulfonate group (-OSO ^ R) of up to six Carbon atoms, an alkylthio group (SR) of up to six carbon atoms, a sulfonamide (SO ₂ NH ₂ -SO ₂ NR ₂ ) having independently up to six carbon atoms in each alkyl moiety, an amido group (NRCOR) having independently up to six carbon atoms in each alkyl moiety , an alkylsulfonaraid (NRSO ₂ R) having independently up to six carbon atoms in each alkyl moiety, an alkylthiocarbonyl group (CSR) of up to six carbon atoms, a thioarnido group (NRCSR) independently having up to six carbon atoms in each alkyl moiety, an alkylfulfonamide (NRSOR) independently up to six carbon atoms in each alkyl moiety, an imido group (N (COR) COR) having independently up to six carbon atoms fa toraen in jederAlkylkomponente, an unsubstituted or substituted, straight or verzvveigtkettiges lower (C ^ -CG) alkyl, (C, -C _ß) cycloalkyl or aryl, wherein the substituent may be on the alkyl moiety one or more identical or different, Hydroxy, halogen, cyano, nitro or an alkoxy group (OR) of up to four carbon atoms, an amino group (NH ₂ ), an alkylamino group (NMR) of up to six carbon atoms, a dialkylamino group (NR ₂ ) having independently up to six carbon atoms in each alkyl moiety, a carboxy group (CO ₂ H), a carbalkoxy group (CO ₂ R) of up to six carbon atoms, an alkylcarbonyl group (COR) of up to six carbon atoms, an alkanoyloxy group (OCOR) of up to six carbon atoms, a carboxamide group (CONH ₂ , CONHR or CONR ₂ ) having independently up to six carbon atoms in each alkyl moiety, a carbamoyloxy group (OCONH ₂ , OCONHR

or OCONRp) having independently up to six carbon atoms in each alkyl moiety, a sulfhydryl, a sulfinyl group (-SOR) of up to six carbon atoms, a sulfonyl group (-SO ₂ R) of up to six carbon atoms, a sulfonate group (-OSO ₂ R) having up to six carbon atoms, an alkylthio group (SR) having up to six carbon atoms, a sulfone amide (SO ₂ NH ₂ , SO ₂ NHR or SO ₂ NR ₂ ) having, independently, up to six carbon atoms in each alkyl component, an amino group ( NRCOR) having independently up to six carbon atoms in each alkyl moiety, an alkylsulfonamide (NRSO ₂ R) having independently up to six carbon atoms in each alkyl moiety, an alkylthiocarbonyl group (CSR) of up to six carbon atoms, a thioamido group (NRCSR) of independently up to six Carbon atoms in each alkyl moiety, an alkylsulfonamide (NRSOR) having independently up to six carbon atoms in each alkyl moiety, an iridido group (34 (COR) COR) mi t is independently up to six carbon atoms in each alkyl moiety, or an aryl group wherein R is an alkyl group of the specified number of carbon atoms;

12, wherein R and R are independently for each

Carbon atom of a chain;

G (C 1 -C 8) -cycloalkyl, unsubstituted or substituted aryl or R ⁴ -Q ;

η is an integer from 0 to 10.

Furthermore, the compositions contain at least one agronomically acceptable carrier »

In formula I, halogen can be selected from fluorine, chlorine, bromine or 3OD.

Cycloalkyl can be selected from cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyciononyl, cyclodocyl, cycloundecyl and cyclododecyl.

Aryl can be selected from phenyl optionally substituted with 1 to 7 substituents independently selected from W; Naphthyl optionally substituted with 1 to 7 substituents independently selected from W; a 5-membered heterocyclic ring having up to 2 nitrogen atoms, up to 2 oxygen atoms, up to 2 sulfur atoms and up to 4 carbon nucleus atoms, optionally substituted by 1 to 4 substituents independently selected from W; or a 6-membered heterocyclic ring having up to 3 nitrogen atoms, up to 2 oxygen atoms, up to 2 sulfur atoms and 1 to 5 carbon nucleus atoms, optionally substituted by 1 to 4 substituents independently selected from VV. Representative examples of 5- and 6-membered heterocyclic rings include pyrryl, furyl, thiophenyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, pyridinyl, pyrimidyl, etc.

A process for preparing 1-substituted-4-substituted-4,5-dihydro-1H-pyrazoles (active ingredient), dissolving an 1-substituted-4,5-dihydro-1H-pyrazole in an aprotic solvent, mixing a strong one Base with the resulting solution, deprotonation at the 4-position of the pyrazole ring and then adding an alkylating or Äcylierungsmittels, wherein the dissolved in the aprotic solvent l-substituted-4,5-dihydro-1'ri-pyrazole a 1 -subs tit 4-substituted onusubstituier t it must be 4,5-dihydro-lH-pyrazole, if the required end product is an l-substituted-4,4-disubstituted-4,5-dihydro-lH-pyrazole.

- 7 -

A second process for the preparation of compounds wherein Y is a group of formula

-CG (group B) involves the treatment of a beta-dicarbonyl compound of formula II;

" / \

AC-CH ₂ - C - G · - II

wherein A, X and G are as hereinbefore defined, with a mixture of hydrazine and formaldehyde to produce a 3-aryl-4-mono-substituted-4,5-dihydropyrazole of formula III; ,

A C - G

CH

H wherein A, X and G are as defined above.

Treatment of the dihydropyreasyl of formula III with an aryl isocyanate provides the N-aryl-3-aryl-4-mono-substituted-4,5-dihydropropyrazole-1-carboxamides.

Further treatment of this 1-substituted-4-mono-substituted-4,5-dihydropyrazole-1-carboxamide with a base followed by an alkylating agent or acylating agent gives the M-aryl-3-aryl-4,4-disubstituted-4-active , 5-dihydropyrazol-i-carboxamide.

-S

The compounds used as active ingredient are N-aryl-3-aryl-4 _# 5-dihydro-1H-pyro-2-ol-1-carboxamides which are disubstituted at the 4-position of the pyrazole ring and 4,5-dihydro-1H- pyrazole-1-carboxamides monosubstituted at the 4-position of the pyrazole ring, the monosubstituted compounds having 1-oxo or 1-thiono functionality at the 4-position of the pyrazole ring. The substituents which may be covalently bonded to the 4-position of the monosubstituted or disubstituted pyrazole ring are defined by Y and Z in formula I. It should be noted that certain compounds of the invention may exist as geometric isolates, ie enantiomers or diastereomers. The invention includes compounds and compositions as described herein comprising substantially pure dextrorotatory, levorotatory or racemic mixtures of the compounds.

The 4,5-dihydro-1H-pyrazole-1-carboxamides according to the invention are intended to comprise 4,5-dihydro-1H-pyrazole-1-thiocarboxamides and 4,5-dihydro-1H-pyrazole-1-iminocarboxamides. When U in Formula I is oxygen then the compound is an oxocarboxamide, when U in Formula I is sulfur then the compound is a thiocarboxamide and when U is NQ then the compound is an iminocarboxamide, the preferred U substituent is oxygen ,

The relationship between Y and Z is such when Y is lower (straight) or branched, unsubstituted or substituted (C ₁ -C ₅ ) alkyl, unsubstituted or substituted aryl, (group A), Z is (Cv-C, -) - cycloalkyl, unsubstituted or substituted aryl or RQ, with the proviso that Z is not hydrogen and Z is not methyl, when C is (group B),

Y - C-G, where X and G are the same as described above for formula I

_ g -

have deutunq, Z may be hydrogen, (C -C _A) -cycloalkyl, unsubstituted or substituted aryl or R -Q.

The only compounds of the invention which may be monosubstituted at the 4-position of the pyrazole ring (i.e., where Z is hydrogen) are those in which Y is X.

- C -, and these monosubstituted compounds

0 s

Il

have necessarily 1-oxo (-C) or 1-thiono (-C) functionality at the 4-position of the pyrazole ring. Otherwise, the compounds according to the invention are disubstituted at the A position of the pyrazole ring.

Possible Z substituents when Y is A include, but are not limited to, alkyl, aryl, aralkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, cyanoalkyl, carboalkoxy, carboalkoxyakyl, carboxamido, carboxyamidoalkyl, N-alkylcarboxamido, N-alkylcarboxamidoalkyl , N, N-dialkylcarboxamido, N, N-dialkylcarboxamidoalkyl, hydroxyalkyl, ketoalkyl, ketoaryl, thionoalkly, thionoaryl, iminoalkyl, iminoaryl, halogen, hydroxy, carboxy, dithiocarboxy, dithiocarboxyalkyl or dithiocarboalkoxy.

Preferred Z substituents when Y is group A are phenyl, 4-chlorophenyl, carbomethoxy, carboethoxy, dimethylcarbamoyl, acetyl, propionyl, benzoyl, butyl, 2-methylthiomethyl, 3-cyanopropyl, 2-methylsulfonylethyl or carbomethoxymethyl.

Possible Z substituents when Y has 1-oxo or 1-thiono functionality (group B) as illustrated in formula I include, but are not limited to: hydrogen, alkyl, aryl, aralkyl, haloalkyl, alkoxyalkyl , Alkylthioalkyl, alkylsulfinylalkyl, cyanoalkyl, carboalkoxy, carboalkoxyalkyl,

- 10 -

Carboxamido, carboxymidylalkyl, N-alkylcarboxamides, N-alkylcarboxamidoalkyl, N, N-dialkylcarboxamido, N, N-dialkylcarboxamidoalkyl, hydroxyalkyl, ketoalkyl, ketoaryl, thionoalkyl, thioncaryl, iminoalkyl, iminoaryl, halogen, hydroxy, carboxy, dithiocarboxy, dithiocarboxyalkyl or dithiocarboalkoxy.

Preferred Z substituents when Y is 1-oxo or 1-thiono functionality (group B) are hydrogen, methyl, phenyl, 4-chlorophenyl, 4-trifluoromethylphenyl, 4-trifluoromethoxyphenyl, 4-irifluorothiomethoxyphenyl, 4-difluoromethoxyphenyl or 4- Difluorbromthiomethoxyphenyl. The most preferred substituent is methyl.

When said compounds are monosubstituted at the 4-position (group B), the compounds having 1-oxo functionality at the Y substituent are preferred.

Examples of substituents for G include hydrogen, alkoxy, thioalkoxy, alkyl, hydroxy, alkoxyalkyl, thioalkoxy ^ alkyl, alkoxyalkoxy, thioalkoxyalkoxy, amino, alkylamino, dialkylamino, carbalkoxy, cyano, ketoalkyl and alkyl substituted by alkoxy, thioalkoxy, carbalkoxy, cyano or alkylheteroalkyl. Preferred G substituents include methyl, ethyl, methoxy, ethoxy, hydroxy. Dimethylamino and phenyl. Most preferred are methoxy, ethoxy or dimethylamino.

Substituant A may be aryl or substituted aryl. The preferred A substituent is unsubstituted or substituted phenyl, and most preferably substituted phenyl. While the phenyl group may be substituted by up to 5 substituents, it is preferred that it be unsubstituted or monosubstituted or disubstituted by the same or different substituents, and most preferably that the phenyl group be replaced by the para substituent monosubsti-

A4

Preferred phenyl substituents include fluoro, chloro, bromo, trifluoromethyl, trifluoromethoxy, difluoromethoxy or methyl. The most

Preferred substituents are chlorine, bromine, trifluoromethyl, trifluoromethoxy or difluoromethoxy at the 4-position on the benzene ring. ; - "'.'''." / .. ^y:; '/' _:. ':. '': '' : '.;. '

Substituent B may be aryl or substituted aryl. The preferred B substituent is unsubstituted or substituted phenyl, and most preferred is substituted phenyl having up to two identical or different substituents in the 3- and / or 4-position. When substituent B is monosubstituted, the phenyl group is preferably substituted in the para position. Preferred substituents include fluoro, chloro, bromo, trifluoromethyl, trifluoromethoxy, difluoromethoxy, carbomethoxy, carboethoxy, carboisopropoxy, methylthio or methylsulfonyl. The most preferred substituents include chloro, bromo, carbomethoxy, carboethoxy, carboisopropoxy, difluoromethoxy, trifluoromethoxy, trifluoromethyl, methylthio or methylsulfonyl.

Representative examples of substituent V include alkyl, branched alkyl, cycloalkyl, aryl, or R-Q wherein Q and R are as defined for formula I above. Preferably V is hydrogen, lower straight or branched chain, unsubstituted or substituted (C ₁ - C ₆ ) alkyl, lower (C 1 -C 15) alkoxy, lower (C 1 -C ₆ ) alkylsulfenyl, unsubstituted or substituted arylsulfenyl, lower (C 1 -C 6) carboalkoxy, cyano, lower (C 1 -C 6) alkylheteroalkyl, wherein is alkoxy, lower (C ^ -C ^ J-alkylsulfenyl, lower (C ₁ -C ₄₎ -Cärboalkoxy, cyano or lower (C ^ CJ-heteroalkyl Am - the substituent on the alkyl is lower (C ₁ -C.). Most preferred are hydrogen, methyl, methylsulfenyl, 2-nitrophenylsulfenyl, carbomethoxy, acetyl, trifluoroacetyl, formyl or methoxalyl.

  )

Aryl may be selected from phenyl optionally substituted with 1 to 5 substituents independently selected from W;

Naphthyl optionally substituted with 1 to 7 substituents independently selected from W; a 5-membered heterocyclic ring containing up to 2 nitrogen atoms, up to 2 oxygen atoms, up to 2 sulfur atoms and up to 4 carbon nucleus atoms, optionally substituted by 1 to 4 substituents independently selected from W; or a 6-membered heterocyclic ring having up to 3 nitrogen atoms, up to 2 oxygen atoms, up to 2 sulfur atoms and 1 to 5 carbon nucleus atoms, optionally substituted by 1 to 4 substituents independently selected from W. Representative examples of 5- and 6-membered heterocyclic rings include pyrryl, furyl, thiophenyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, pyridyl, pyrimidyl, etc.

W is halogen, cyano, nitro, R ¹ , CO ₂ R ¹ , CONR ¹ R ² , CR ¹ SCR ² R ³ , CSCR ¹ , SR ¹ , OR ¹ , NR ¹ R ² , SOR ¹ , SO ₂ R ¹ , OSOgR ¹ , NR ¹ COR ² , SF ₅ ,

, OCF ₃ , OCF ₂ H, SCF ₃ , OCF ₂ Br, SCF ₂ Br, SCF ₂ Cl, SCFgH, NR SO ₂ R ² or N (C0R ¹ ) C0R ² .

Since l-substituted-4-substituted-4,5-dihydro-iH-pyrazoles of the formula I can have acidic or basic characteristic groups, they can form new salts with suitable bases or acids, which also have pesticidal activity. Typical salts are the agronomically acceptable metal salts, ammonium salts and acid addition salts. The metal salts include those in which the metal cation is an alkali metal cation such as sodium, potassium, lithium, etc .; Alkaline earth metal cation such as calcium, magnesium, barium, strontium, etc .; or heavy metal cation such as zinc, manganese, copper (II), copper (I), iron (III), iron (II), titanium, aluminum, etc. Among the ammonium salts are those in which the ammonium cation has the formula NR R R R, where each of R, R,

7, R and R independently represent a hydrogen atom, a hydroxy group, a (C ₁ -C 4) -alkoxy group, - a (C ₁ -C ₂₀ ) -alkyl group, a

(C ₃ -C 6) -alkenyl group ₍ a (C ₃ -C ₈ ) -alkynyl group, a (C ₂ -C ₃ ) -hydroxyalkyl group, a (C ₂ -C ₈ ) -alkoxyalkyl group, a (Co-CgJ-arainoalkyl group), a (C ₂ -Cg) -haloalkyl group, an amino group, a (C ₁ -C ₄ ) -alkyl or (C ₁ -C ₄ ) -dialkylamino group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted phenylalkyl group having up to four Carbon atoms in the alkyl moiety, or any two of R, R, R or R can be taken together to form with the nitrogen atom a 5- or 6-membered heterocyclic ring, optionally with up to an additional heteroatom (e.g., oxygen , Nitrogen or sulfur) in the ring, and preferably saturated, such as piperidino, morpholine pyrrolidino, piperazino, etc., or any three

C g ~ J Q

R, R, R or R may be taken together to form with the nitrogen atom a 5- or 6-membered aromatic heterocyclic ring such as piperazole or pyridine. When the ammonium group contains a substituted phenyl or substituted phenylalkyl group, the substituents are generally selected from halogen atoms, (C ₁ -C ₄ ) -alkyl groups, (C ₁ -C ₄ ) -alkoxy groups, hydroxyl groups, nitro groups, trifluoromethyl groups, cyano groups, amino groups, (C ₁ -C ₄ ) alkylthio groups, etc. Such substituted phenyl groups preferably have up to two such substituents. Representative ammonium cations include ammonium, dimethylammonium, 2-ethylhexylammonium, bis (2-hydroxyethyl) aramonium, tris (2-hydroxyethyl) ammonium, dicyclohexylammonium, J> octylammonium, 2-hydroxyethylammonium, morpholinium, piperidinium, 2-phenethylammonium, 2-methylbenzylammonium, jn Hexylammonium, triethylammonium, trimethylammonium, tri (i2-butyl) -ammonium, methoxyethylammonium, diisopropylararnonium, pyridinium, dialkylammonium, pyrazolium, propargylammonium, dimethylhydrazinium, octadecylammonium, 4-dichlorophenylaramonium, 4-nitrobenzylammonium, benzyltrimethylammonium, 2-hydroxyethyldirethyloctadecylammonium, 2-hydroxyethyldiethyloctylammonium, decyltrimethylammonium, Hexyltriethylammonium, 4-Methylbenzyltrimethylammonium are etc. Among ate acid addition salts

those in which the anion is an agronomically acceptable anion such as hydrochloride, hydrobromide, sulfate, nitrate, perchlorate, acetate, oxalate, etc.

Representative examples of compounds of the invention covered by formula I are listed below.

The examples given under group A include compounds in which Y is a group A substituent corresponding to the meaning explained above for formula I. The examples listed under group B include compounds in which Y is a group B substituent corresponding to the meaning explained above for formula I.

Group A

N, 3,4-tris (4 * -chlorophenyl) -4-tnethyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3,4-tris (4-chlorophenyl) -N, 4-dimethyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-bromophenyl) -4 ~ carboraethoxy-4-methyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N, 3-bis (4-chlorophenyl) -4- (l-ethylpropyl) -4-niethyl-4,5-dihydro-lH-pyrazol-1-carboxaraid

N, 3-bis (4-chlorophenyl) -4- (l-hydroxy-l- (4-fluorophenyl) methyl) -4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

^N, N, 3-Bis (4-chlorophenyl) -4- (1-hydroxyethyl) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4- (l-raethylethyl) -4-raethyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4- (1-methylpropyl) -4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4- (2,3-dibromopropyl) -4-methyl-4,5-dihydrö-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4- (2,3-dichloropropyl) -4-inethyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4- (2-acetoxyethyl) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4- (2-ethylthioethyl) -4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N _# 3-bis (4-chlorophenyl) -4- (2-hydroxyethyl) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N , 3-bis (4-chlorophenyl) -4- (2-hydroxypropyl) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N, 3-bis- (4-chlorophenyl) -4- (2-methoxyethoxymethyl) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4- (2-methoxyethyl) -4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4- (2-methylpropyl) -4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

U, 3-bis (4-chlorophenyl) -4- (2-methylpropyl) -N, 4-dimethyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4- (2-methylsulfonylethyl) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4- (2-methylsulfoxylethyl) -4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N, 3 ~ Bis (4-chlorophenyl) -4- (2-methylthioethyl) -4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4- (2-phenylthioethyl) -4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3 ~ Bis (4-chlorophenyl) -4- (3-azidopropyl) -4-methyl-4,5-dihydrolH-pyrazol-1-carboxaraid

N, 3-bis (4-chlorophenyl) -4- (3-butenyl) -4-methyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N, 3-bis (4-chlorophenyl) -4- (3-chloropropyl) -4-methyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N, 3-bis (4-chlorophenyl) -4- (3-cyanopropyl) -4-methyl-4,5-dihydro-IH-pyrazol-l-carboxaniid

N, 3-bis (4-chlorophenyl) -4- (4-chlorobenzoyl) -4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N, 3-bis (4-chlorophenyl) -4- (4-chlorobutyl) -4-methyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N, 3-bis (4-chlorophenyl) -4- (4-methoxybutyl) -4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4- (5-hexenyl) -4-methyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N, 3-bis (4-chlorophenyl) -4-acetyl-4-methy1-4,5-dihydro-IH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-allyl-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-benzoyl-4-methyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-benzyl-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N _f 3-3is (4-chlorophenyl) -4-butyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-butyl-N, 4-dimethyl-4,5-dihydro-lH-pyrazol-1-carbocamid

N, 3-bis (4-chlorophenyl) -4-carbo (2-dirnethylaminoethoxy) -4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbo (2-dimethylaminoethoxy) -4-methyl-4, S-dihydro-lH-pyrazol-l-carboxamidhydrochloridsalz

N, 3-bis (4-chlorophenyl) -4-carbo (2-methylsulfonylethoxy) -4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

H ₁ 3-Bis (4-chlorophenyl) -4-carbo (2-methylthioethoxy) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbobutoxy-4-methyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N, 3-bis (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-IH-pyrazol-l-carboxaraid

N, 3-bis (4-chlorophenyl) -4-carboisopropoxy-4-methyl-4,5-dihydro-lH-pyrazol-1-carboxaraid

N, 3-bis (4-chlorophenyl) -4-carbomethyloxy-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbomethoxy-4-ethyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N _# 3-bis (4-chlorophenyl) -4-carbomethoxy-4-methyl-N-acetyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbomethoxy-N, 4-dimethyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbomethoxy-N- (1-carbomethoxy-prop-2-yl-thio) -4-methyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N, 3-3is- (4-chlorophenyl) -4-carbomethoxy-N- (2-nitrophenylsulphenyl) -4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N, _J 3-Bis- (4-chlorophenyl) -4-carbomethoxy-N- (3-cyanopropylthio) -4-methyl-4,5-dihydrc-1H-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbomethoxy-N-acetyl-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxthioamid

N, 3-3is- (4-chlorophenyl) -4-carboraethoxy-N-carboethoxy-4-methyl ^ iS-dihydro-lH-pyrazol-l-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbomethoxy-N-carbomethoxythio-4-methyl-4 _L 5-dihydro-1H-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbornethoxy-N-carbophenoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbomethoxy-N-carbovinyloxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N, 3-bis (4-chlorophenyl) ~ 4-carbomethoxy-N-dimethylcarbamoyl-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbomethoxy-N-fQrmyl-4-methyl-4,5-dihydro-lH-pyra2ol-l-carboxamide

N _, 3-Bis (4-chlorophenyl) -4-carbomethoxy-N-methoxymethyl-4-methyl-i-dihydro-1H-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbomethoxy-N-methyloxallyl-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N, 3-bis (4-chlorophenyl) -4-carborethoxy-N-ethylthio-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbomethoxy-N-phenylthio-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N, 3-bis- (4-chlorophenyl) -4-carborethoxy-N-propylthio-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbomethoxy-N-trifluoroacetyl-4-raethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

M, 3-bis (4-chlorophenyl) -4-carboraet: hoxymethyl-4-methyl-4,5-dihydro-lH-pyrazol-1-carboxatnid

N, 3-bis (4-chlorophenyl) -4-carbomethylthiomethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N, 3-8is- (4-chlorophenyl) -4-carbopropoxy-4-raethyl-4,5-dihydro-IH-pyrazol-l-carboxaraid

N, 3-bis (4-chlorophenyl) -4-carboxy-4-methyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-carboxy ~ 4-methyl-4,5-dihydro-IH-pyrazol-1-carboxaniidnatriumsalz

N, 3-bis (4-chlorophenyl) -4-cyano-4-raethyl-4,5-dihydro-lH-pyrazol-1-carboxainid

N, 3-bis (4-chlorophenyl) -4-cyclohexyl-4-methyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N, 3-bis (4-chlorophenyl) -4-diethylcarboxamido-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-dimethylcarboxamido-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N, 3-3is- (4-chlorophenyl) -4-dimethylthiocarbamoyl-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N, 3-bis (4-chlorophenyl) -4-ethyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide.

N, 3-bis (4-chlorophenyl) -4-hexyl-4-raethyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-isobutyryl-4-methyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N, 3-bis (4-chlorophenyl) -4-methoxymethyl-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-methylthiomethyl-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-methylthiothiocarbonyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-pentyl-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-phenyl-N, 4-dimethyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N, 3-bis (4-chlorophenyl) -4-phenyl-N-acetyl ~ 4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-phenyl-N-benzoyl-4-methyl-4,5-

ψ dihydro-1H-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-phenyl-N-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-phenyl-N-carbomethoxythio-4-methyl-4,5-dihydro-lH-pyrazol-1-carboxatnid

H, 3-bis (4-chlorophenyl) -4-phenyl-N-cyano-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxaraid

N, 3-bis (4-chlorophenyl) -4-phenyl-N-methoxymethyl-4-methyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N, 3-bis (4-chlorophenyl) -4-phenyl-N-propionyl-4-methyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N, 3-8is- (4-chlorophenyl) -4-phenyl-N-triraethylacetyl-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3 ~ Bis (4-chlorophenyl) -4-pivaloyl-4-methyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-propionyl-4-raethyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N, 3-bis (4-chlorophenyl) -4-propyl-4-methyl-4,5-dihydro-lH-pyrazol-1-carboxaniid

N, 3-bis (4-dichlorophenyl) -4-phenyl-4-methyl-4, 5-dihydro-IH-pyrazol-l-carboxaraid

N, 3-bis (4-fluorophenyl) -4-butyl-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-3is (4-trifluoromethylphenyl) -4-carbomethoxy-4-methyl-4,5-dihydrp-lH-pyrazol-l-carboxaraid

N- (l-naphthyl) -3- (4-chlorophenyl) -4-carbomethoxy-4,5-dihydrolH-pyrazole-1-carboxamide

N- (2,4-dinitrophenyl) -3- (4-chlorophenyl) -4-carboniethoxy-4- _t, 5-dihydro-1H-pyrazole-1-carboxamide

N- (2-fluoro-4-trifluoromethylphenyl) -3- (3-Chiot ^ -trxfiuormethylphenyl) -4- (3-raethylthiopropyl)--4-methyl-dihydro ~ 4.5

lH-pyrazole-1-carboxamide

N- (2-Fluo-4-trifluoromethylphenyl) -3- (3-chloro-trifluoroethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxaraid

N- (2-Fluoro-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoro-methylphenyl) -4-phenyl-4-me-th1, 4, 5-dihydro-1H-pyrazole-1-carboxamide

N- (2-fluoro-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (2-fluoro-4-trifluorinethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (2-fluoro-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4 _f 5-dihydro-lH-pyrazol-l-carboxamide

N- (2-methyl-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N- (2-methyl-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (2-Methyl-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide -

N- (2-methyl-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazol-l-carbox-

amide

N- (2-methyl-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4- carboethoxy ι ^ -methyl ^ .S-dihydro-lH-pyrazol-l-carboxamide

N- (2-methyl-4-trifluoroethylphenyl) -3- (4-chlorophenyl) -Aphenyl -4-methyl-4 _# 5-dihydro-IH-pyrazole-1-carboxamide

N- (3,4-dichlorophenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N- (3,4-dichlorophenyl) -3- (4-chlorophenyl) -4 ~ phenyl-4-methyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (3 _/ 4-dichlorophenyl) -3-phenyl-4-carbomethoxy-4-methyl-4,5 · dihydro-1H-pyrazole-1-carboxamide

N- (3-3rom-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydrolH-pyra2ol-l-carboxamide

N- (3-bromo-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4 _# 5-dihydro-1H-pyrazole-1-carboxamide

V) N- (3-bromo-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-Brora-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyra2ol-lcarboxamid

N- (3-bromo-4-trifluorinethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy ^ -methyl ^ .S-dihydro-lH-pyrazol-l-carboxamide

N- (3-bromo-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-

methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazol-lcarboxamid

N- (3-bromophenyl) -3- (3-chiοr-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazol-carboxamide-l

N- (3-bromophenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-bromophenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (3-Carboethoxyphenyl) -3- (3-chloro-4-trifluoromethylphenoxy) 4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-1H-pyrazole-1

carboxamide

N- (3-Carboethoxyphenyl) -3- (3-chloro-4-trifluoromethylphenyl) 4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

4-phenyl-4-methyl-4 _f S-dihydro-lH-pyrazol-l-carboxamide

N- (3-carboethoxyphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-carboethoxyphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-raethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-carboethoxyphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-Carboisopropoxyphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-1H-pyrazole-1

carboxamide

N- (3-Carboisopropoxyphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxaraid

N-CS-carboisopropoxyphenyl J-S-CS-chloro-trifluoromethylphenyl) 4-phenyl-4-n-ethyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-Carboisopropoxyphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N- (3-Carboisopropoxyphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxaniid

N- (3-Carboisopropoxyphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4,5-dih _/ ydro-lH-pyrazol-l-carboxamide

N- (3-Carbornenethoxyphenyl) -3- (3-chloro-trifluorinated phenyl) 4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-1H-pyrazole-1- C () carboxamide

N- (3-carbomethoxyphenyl) -3- (3-Chiot ^ trifluoromethylphenyl) -4-caΓboethoxy-4-raethyl-4,5-dihydΓo-lH-pyΓazol l caΓboxamid

N- (3-carbomethoxyphenyl) -3- (3-Chiot ^ trifluoromethylphenyl) -4-phenyl-4-methyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N- (3-carbomethoxyphenyl) -3- (4-chlorophenyl) -4- (3-raethylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (3-carbomethoxyphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-1-carboxaraid

N- (3-carbomethoxyphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-chloro-4-trifluorraethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N- (3-chloro-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-iH-pyrazole-1-carboxamide

te = S ä % f "J

N- (3-chloro-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxylazole ~

N- (3-chloro-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyra2ol-l-aarbGX-

N- (3-chloro-4-trifluorroethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy ^ -methyl ^ .S-dxhydro-lH-pyrazol-l-carboxamide

N- (3-chloro-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-chlorophenyl) -3- (4-chlorophenyl) -4-carboraethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxaraid

N- (3-chlorophenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4 _# 5-dihydro-1H-pyrazole-1-carboxamide

N- (3-cyano-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-raethyl-4,5-dihydro-

lH-pyrazole-1-carboxamide

N- (3-cyano-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoro

raethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (3-Cyano-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-4- _t, 5-dihydro-1H-pyrazole-1-carboxamide

N- (3-cyano-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide.

N- (3-cyano-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-cyano-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4 _# 5-dihydro-1H-pyrazol-1-carboxamide

trifluorinethylphenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazol-1-carboxaraid

N- (3-di-fluoromethoxy-4-trifluoromethylphenyl) -3- (3-chloro-4- j trifluorraethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N- (3-difluoromethoxy-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4 ~ methyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N- ( 3-Difluoromethoxy-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N- (3-Difluoro-ethoxy-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-Difluoromethoxy-4-trifluoroethylphenyl) -3- (4-chlorophenyl) 4-phenyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-Difluoro-methoxyphenyl) -3- (3-chloro-4-trifluoromethyl-phenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-Difluoromethoxyphenyl) -3- (3-chloro-4-trifluoromethylphenyl) 4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-di-fluorene-thoxyphenyl) -3- (3-chloro-trifluoro-1-phenyl) -4-phenyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carbamide

N- (3-difluoromethoxyphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (3-difluoromethoxyphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-difluoromethoxyphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl ^ jS-dihydro-lH-pyrazol-l-carboxamide

N-iS-DimethylsulfonaraidophenylJ-S-iS-chloro ^ trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-methyl-4 _f 5-dihydro-lH-pyrazole-1-carboxamide

N- (3-Diraethylsulfonamidophenyl) -3- (3-chloro-4-triflubrmethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-lcarboxamid

N- (3-Dimethylsulfonarnidophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phsnyl-4-methyl-4,5-dihydro-lH-pyrazol-l-carbox-

N- (3-Dimethylsulfonaraidophenyl) -3- (4-chlorophenyl) -4- (3-

methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazol-lcarboxamid

N- (3-Dimethylsulfonamidophenyl) -3- (4-chlorphsnyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-Dimethylsulfonamidophenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4 _# 5-dihydro-1H-pyrazole-1-carboxamide

N- (3-fluoro-4-trifluoroolylthyl-phenyl) -3- (3-chloro-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-

lH-pyrazol-1-carboxamide

Ν- (3-Fluoro-4-trifluoromethyl-phenyl) -3- (3-chloro-4-trifluoro-methyl-phenyl) -4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-fluoro-trifluorothyl-phenyl) -3- (3-chloro-trifluoromethylphenyl) -4-phenyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-Fluoro-4-trifluoroethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-fluoro-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (3-fluoro-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazol-1-carboxaraid

N- (3-Methoxy-4-trifluoromethylphenyl) -3- (3-chloro-1-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-IH-pyrazole-1 carboxaraid

N- (3-Methoxy-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluorinated phenyl) -4-carboethoxy-4-methyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N- (3-Methoxy-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-methoxy-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-methoxy-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-ciihydro-lH-pyrazol-l-carboxamide

N- (3-methoxy-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (3-methyl-4-trifluoro-ethylphenyl) -3- (3-chloro-trifluoromethyl-phenyl) -4- (3-methyl-1-propyl) -4-methyl-4, 5-dihydro-1, 5-pyrazole; carboxamide

N- (3-methyl-4-trifluoromethylphenyl) -3- (3-Chiot ^ trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (3-methyl-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazol-l-

carboxamide

N- (3-Hethyl-4-trifluorraethylphenyl) -3- (4-chlorophenyl) -4- (3 x

methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazol-lcarboxamid

N- (3-methyl-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

jsj_ (3-methyl-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-ethyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-methylsulfonyl-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-methyl-4, S-dihydro-lH-pyrazol-l-carboxaraid

N- (3-methylsulfonyl-4-trifluoromethylphenyl) -3- (3-chlοr-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N- (3-methylsulfonyl-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluorraethylphenyl) -4-phenyl-4-methyl-4,5-dihydro-IH-pyrazol-1-carboxaraid

N- (3-methylsulfonyl-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazol-l-

carboxamide

N- (3-methylsulfonyl-4-trifluoro-ethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-methylsulfonyl-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-methylsulfonylphenyl) -3- (3-chloro-3-trifluorinated phenyl) 4- (3-methylthiopryl) -4-methyl-4,5-dihydro-1H-pyrazole-1

carboxamide

N- (3-methylsulfonylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-cahenoethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-caΓboxaraid

N- (3-methylsulfonyl-phenyl-3- (3-chloro-4-trifluoromethyl-phenyl) -4-phenyl-4-yl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-methylsulfonylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-methylsulfonylphenyl) -3- (4-chlorophenyl) -4-carboathoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-methylsulfonylphenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (3-methylsulfonylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-methylthio-4-trifluorroethylphenyl) -3- (3-chloro-4-trifluorraethylphenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-

dihydro-lH-pyrazol-1-carboxaraid

N- (3-Me, methylthio-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carbethoxy-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (3-methylthio-4-trifluoromethylphenyl) -3- (3-chloro-4-tri-

fluoromethylphenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (3-methylthio-4-trifluoroethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4 _# 5-dihydro-1H-pyra-2-ol

carboxamide

N- (3-methylthio-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-methylthio-4-trifluorinethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (3-methylthiophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazol-l-

carboxamide

N- (3-methylthiophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4 ~ methyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (3-methylthiophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-4 ₁ 5-dihydro-1H-pyrazole-1-carboxamide

N- (3-methylthiophenyl) -3- (4-chlorophenyl) -4- (3-raethylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-methylthiophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazole ~ l-carboxamide

N- (3-methylthiophenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazol-i-carboxamide

N- (3-methylthiophenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (3-nitro-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-) -H-pyrazole-1-carboxamide

N- (3-nitro-4-tertiaryfluorophenyl) -3- (3-chloro-3-trifluoromethyl)

methylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (3-nitro-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-4 _f 5-dihydro-lH-pyrazol-lcarboxamid

N- (3-nitro-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4- (3

methylthiopropyl) -4-raethyl-4,5-dihydro-lH-pyrazol-lcarboxamid

N- (3-nitro-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carbo§thoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxatnid

N- (3-nitro-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazol-l-caröoxamid

N- (3-trifluoromethoxy-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-trifluoromethoxy-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluorniethylphenyl) -4-carboethoxy-4-tnethyl-4,5-dihydro-

IH-pyrazole-l-carboxamide

N- (3-trifluoromethoxy-4-trifluoromethylphenyl) -3- (3-chloro-4-

trifluoromethylphenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (3-trifluoromethoxy-4-trifluoromethylphenyl) -3- (4-chlorophenyl) 4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-trifluoroethoxy-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-caΓboxafnid

N- (3-trifluoromethoxy-4-trifluoromethylphenyl) -3- (4-chlorophenyl) 4-phenyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-trifluorophenoxyphenyl) -3- (3-chloro-trifluoromethylphenyl) 4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-1H-pyrazole-1

carboxamide

N- (3-trifluorophenoxyphenyl) -3- (3-chloro-trifluoromethylphenyl) 4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-trifluoroethoxyphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxaraid

N- (3-trifluoromethoxyphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (3-trifluoromethoxyphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4 _# 5-dihydro-1H-pyrazole-1-carboxamide

N- (3-trifluoromethoxyphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4 _/ 5-dihydro-1H-pyrazole-1-carboxamide

N- (3-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) 4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-1H-pyrazole-1

carboxaraid

N- (3-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide ₅ .

N- (3-trifluoromethylphenyl) -3- (3-chloro-trifluorothylphenyl) -4-phenyl-4-methyl-4,5-dxhydro-1H-pyrazole-1-carboxamide

N- (3-Trifluorraethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-raethyl-4,5-dihydro-lH-pyrazol-l-carboxaraid

N- (3-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxaraid

N- (4- (3-methylthiopropyl) phenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-LH

pyrazol-1-carboxaraid

N- (4- (3-methylthiopropyl) phenyl) -3- (4-chlorophenyl) -4- (3-

methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazol-lcarboxamid

N- (4-bromophenyl) -3- (3-chloro-4-trifluorraethylphenyl) -4- (3-raethylthiopropyl) -4-acetyl-4,5-dihydro-lH-pyrazol-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-ca'rbomethoxy-4,5-dihydro-lH-pyrazol-l-

carboxamide

F4 (4-8roniphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-ethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N ~ (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazol-lcarboxamid

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-methyl-N- (2-methoxyethylsulfenyl) -4,5-

dihydro-lH-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (3-chloro-trifluorothylphenyl) -4- (3-methylthiopropyl) -4-methyl-N- (2-nitrophenylsulfenyl) -4,5-dihydro-1H-pyrazole-1 -carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluorinethy! Phenyl) -4- (3

meth ^ lthiopropyl) -4-methyl-N-acetyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-ethyl-N-carboethoxy-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-ethyl-N-carbomethoxy-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3

methylthiopropyl) -4-methyl-N-carboraethoxycarbonyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-methyl-N-carbomethoxysulfenyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Bromophenyl) -3- (3-chloro-trifluoroenylene phenyl) -4- (3-methylthiopropyl) -4-methyl-N-dimethylcarbamoyl-4,5-dihydro

IH-pyrazole-l-carboxamide

N- (4-Broraphenyl) -3- (3-chloro-trifluorinated phenyl) -4- (3-methylthiopropyl) -4-methyl-N-formyl-4,5-dihydro-1H-pyrazole-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-methyl-N-methoxymethyl-4,5-dihydro-LH

pyrazole-1-carboxamide

N -. (4-.Bromphenyl) -3- (3-chloro-4-trxfluormethylphenyl) -4- (3-raethylthiopΓopyl) -4-Inethyl- ^ 3-methyl-4 _# 5-dihydΓO-lH-pyΓa2ol-

1-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-methyl-N-methylsulphenyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N- (4-8romphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-methyl-N-trifluoroacetyl-4,5-dihydro-LH

pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4- (2-chloroallyl) -4,5-dihydro-IH-pyrazol-i-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4- (2-methylthioethyl) -4,5-dihydro-lH-pyra2ol-l-

carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4- (3-cyanopropyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4- (4-chlorophenyl) -4,5-dihydro-IH-pyrazole-l-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy ~ 4- (4-difluoromethoxyphenyl) -4,5-dihydro-lH-pyrazol-l-

carboxamide

M - (4> 3-Methyl-phenyl) -3- (3-chloro-4-trifluoromethyl-phenyl) -4-carboethoxy-4- (4-trifluoro-araoxyphenyl) -4 _L 5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Bro (n-phenyl) -3- (3-chloro-4-trifluoromethyl-phenyl) -4-carboethoxy-4- (4-trifluoromethyl-phenyl) -4 _i 5-dihydro-1H-pyra-2-ol

carboxamide

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carbo-8-thoxy-4-acetyl-4 _# 5-dihydro-1H-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-allyl-4,5-dihydro-1H-pyrazole-1-carboxaraid

N- (4-bromophenyl) -3- (3-chloF-4 ~ trifluoromethylphenyl) -4-carboethoxy-4-benzyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-carbomethoxy-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Srphenyl) -3- (3-chloro-4-trifluoroethylphenyl) -4-carboethoxy-4-ethyl-4, S-dihydro-1H-pyrazole-1-carboxamide

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-rnethallyI-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoro-ethylphenyl) -4-carbo-methoxy-4-dethoxymethyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxaraid

jsj_ (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-N- (2-methoxyethylsulfenyl) -4,5-dihydro-LH

pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-raethyl-N- (2-nitrophenylsulfenyl) -4,5-dihydro-LH

pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (3-Chiot ^ trifluoromethylphenyl) -4-carboethoxy-4-methyl-N-acetyl-4,5-dihydro-lH-pyra2ol-l-carboxamide

M- (4-Broraphenyl) -3- (3-chloro-trifluorinated phenyl) -4-carboethoxy-4-ethyl-N-caΓboethoxy-4,5-dihydro-1H-pyo-2a-ol

carboxamide

M_ (4_3romphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-N-caΓbotnethoxy-4,5-dihydΓö-lH-pyΓa2ol-l-

carboxamide

N- (4-bromophenyl) -3- (3-chloro-trifluorothylphenyl) -4-chloroethoxy-4-methyl- ^ 3-carbomethoxy-cyanocarbonyl-4,5-dihydroloH-

pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-N-carbomethoxysulfenyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluorraethylphenyl) -4-carboethoxy-4-methyl-N-dimethylcaΓbamoyl-4,5-dihydΓO-lH-pyΓazol-

1-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-N-formyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4 ~ trifluoromethylphenyl) -4-carboethoxy-4 ~ raethyl-N-methoxyraethyl-4,5-dihydro-lH-pyrazol-i-

carboxatnid

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-N-methyl-4 _# 5-dihydro-1H-pyrazole-1-carboxamide

M- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-N-methylsulphenyl ~ 4,5-dihydro-lH-pyrazol-l-

carboxamide

N- (4-bromophenyl) -3- (3-chloro-trifluorothyl-phenyl) -4-chloroethoxy-methyl-N-trifluoroacetyl-.s-dihydro-1H-pyrazole-1;

carboxamide

iM (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methylthiomethyl-4,5-dihydro-lH-pyrazol-l-carboxaraid

N- (4-Broniphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-phenyl-4 _# 5-dihydro-1H-pyrazole-1-l-carboxamide

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-methyl-4- (2-chloroallyl) -4 _/ 5-dihydro-1H-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-methyl-4- (2-methylthioethyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-raethyl-4- (3-cyanopropyl) -4, S-dihydro-lH-pyrazol-l-carboxamide

N- (4-Broraphenyl) -3- (3-chloro-4-trifluormethylphenyI) -4-methyl-4- (4-chlorophenyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-methyl ~ 4- (4-difluormethoxyphanyl) -4 _i S-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluorraethylphenyl) -4-methyl-

4- (4-trifluoromethoxyphenyl) -4,5-dihydro-lH-pyrazol-lcarboxamid

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-methyl-4- (4-trifluoromethylphenyl) -4,5-dihydro-lH-pyrazol-lcarboxamid

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-methyl-4-acetyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-3romphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-tnethyl-4-allyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (3-'chlor-4-trifluoromethylphenyl) -4-methyl-

4-benzyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N_ (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-raethyl-4-carbomethoxy-4,5-dihydro-lH-pyra2ol-l-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-methyl-4-ethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Bromo-phenyl) -3- (3-chloro-4-trifluoromethyl-phenyl) -4-methyl-4-tetrahydro-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-ethyl-4-niethoxy-ethyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-methyl. 4-methylthiomethyl-4,5-dihydro-1H-pyrazole-1-carboxamide

M '' (4 "bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-methyl-4-phenyl-4 _, 5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4- (2-chloroallyl) -4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluorraethylphenyl) -4-phenyl-4- (2-methylthioethyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-3romphenyl) -3- (3-Chiot ^ trifluoromethylphenyl) -4-phenyl-4- (3-cyanopropyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trxfluormethylphenyl) -4-phenyl-4- (4-chlorophenyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Brompheriyl) -3- (3-chloro ^ trifluoromethylphenyl) -4-phenyl-4- (4-difluoromethoxyphenyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluorinethylphenyl) -4-phenyl-

4- (4-trifluoromethoxyphenyl) -4,5-dihydro-lH-pyrazol-lcarboxamid

N- (4-Bromophenyl) -3- (3-chloro-3-trifluoromethylphenyl) -4-phenyl-4- (4-trifluoromethylphenyl) -4, S-dihydro-1H-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (3-chloro-trifluorothylphenyl) -4-phenyl-4-acetyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Bromophenyl) -3- (3-chloro-1-trifluoromethyl-phenyl) -4-phenyl-4-allyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-benzyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-carbomethoxy-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Bromophenyl) -3- (3-chloro-1-trifluoromethyl-phenyl) -4-phenyl-4-ethyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl 4-methallyl-4, S-dihydro-1H-pyrazole-1-carboxamide

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methoxymethyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (3-Chiot ^ -trifluorraethylphenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxaraid

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-N- (2-methoxyethylsulfenyl) -4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Broraphenyl) -3- (3-Chiot ^ trifluoromethylphenyl) -4-phenyl-4-methyl-N- (2-nitrophenylsulfenyl) -4,5-dihydro-lH ~ pyrazol-l-

carboxamide

N- (4-bromophenyl) -3- (3-Chiot ^ trifluoromethylphenyl) -4-phenyl-

4-methyl-N-acetyl-4,5-dihydro-1-i-pyrazole-1-carboxamide j »

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl = 4-methyl-N-carboethoxy-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (3-cblor-4-trifluoromethylphenyl) -4-phenyl-4-methyl-N-carbomethoxy-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-N-carborothethoxycarbonyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-pheny1-4-methyl-N-carbornethoxysulfenyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trif1uormethylphenyl) -4-phenyl 4-methyl-N-4-dimethylcaΓbamoyl _ί 5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-

ν.

4-methyl-N-formyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (3-chloro-3- (trifluoromethylphenyl) -4-phenyl-4-methyl-N-methoxyniethyl-4,5-dxhydro-1H-pyrazole-1-carboxanilide

N- (4-bromophenyl) -3- (3-chloro-4-, trifluoromethylphenyl) -4-phenyl-4-methyl-N-methyl-4,5-dih'ydro-lH-pyrazol-l-carboxamide

W- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-N-ethylsulfenyl-4 _# 5-dihydro-1H-pyrazol-1-carboxaraid

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-N-trifluoroacetyl-4,5-dihydro-lH-pyra2ol-l-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluormethy! Phenyl) -4-phenyl-4-methylthiomethyl-4, '5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Broraphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-acetyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-carbomethoxy-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-ethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-N- (2-methoxyethylsulfenyl) -4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-N- (2-nitrophenylsulfenyl) -4,5-dihydro-IH-pyrazol-lcarboxamid

N- (4-bromophenyl) -3- (4-chlorophenyl) -4 - (3-methylthiopropyl) -4-methyl-N-acetyl-4,5-dxhydro-lH-pyrazol-l-carboxamide

N- (4-Broraphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-N-carboethoxy-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-3romphenyl) -3- (4-chlorophenyl) -4- (3-rnethylthiopropyl) -4-methyl-N-carboinethoxy-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-N-carboroethoxysulfenyl-4,5-dihydro-lH-pyrazol-lcarboxaraid

N- (4_Bromphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-N-dimethylcarbamoyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4- (3-rnethylthiopropyl) -4-methyl-N-formyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-N-raethoxymethyl-4,5-dihydro-lH ~ pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-raethyl-N-tnethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-N-methylsulphenyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl} -4-methyl-N-trifluoroacetyl-4,5-dihydro-lH-pyrazöl-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methylthiomethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) ~ 4-phenyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N_ (4_Bromphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (2-chloroallyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

ISL (4-Broraphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (2-methylthioethyl) -4,5-dihydro-lH-pyrazol-l - carboxamide

N- (4-8romphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (3-cyanopropyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

} sj_ (4-Bromo-phenyl) -3- (4-chloro-phenyl) -4-carboethoxy-4- (4-chloro-phenyl) -4,5-dxhydro-1H-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (4-difluoromethoxyphenyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-3romphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (4-trifluoromethoxyphenyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (4-trifluoromethylphenyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-acetyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4 ~ chlorophenyl) -4-carboethoxy ~ 4-allyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-benzyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-carbomethoxy ~ 4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) ~ 4-carboethoxy-4-ethyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methallyl-4,5 dihydro-lH-pyra2ol-l-carboxaraid

N- (4-Broraphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-raethoxymethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyra2ol-l ~ carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-raethyl-N- (2-methoxyethylsulfenyl) -4,5-dihydro-lH-pyra2ol-l-carboxamide

N- (4-bromo-phenyl) -3- (4-chloro-2-phenyl) -4-carboethoxy-4-methyl-N- (2-nitrophenylsulfenyl) -4 _# 5-dihydro-1H-pyra-2-ol-1-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-acetyl-4,5-dihydro-lH-pyra2ol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-carboethoxy-4,5-dihydro-lH-pyra2ol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-carbomethoxy-4,5-dihydro-lH-pyra2ol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-raethyl-N-carbomethoxycarbonyl-4,5-dihydro-lH-pyra2ol-l-carboxamide

N- (4-Broniphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-carbomethoxysulfenyl-4,5-dihydro-lHrpyra2ol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) ~ 4-carboethoxy-4-methyl-N-dimethylcarbamoyl-4,5-dihydro-lH-pyra2ol-l-carboxamide

N- (4-Broraphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-raethyl-N-forrayl ^ jS-dihydro-lH-pyrazol-l-carboxaraid

N- (4-bromophenyl) -3- (4 ^ chlorophenyl) -4-carboethoxy-4-methyl-N-methoxyraethyl-4,5-dlhydro-lH-pyrazol-l-carboxamide

N- (4-3romphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Broraphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-raethyl-N-methylsulphenyl-4,5-dxhydro ~ lH-pyrazol-l-carboxaniid

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-trifluoroacetyl ^^ - dihydro-lH-pyrazol-l-carboxaraid

N- (4-bromo-phenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-5-methyl-1-methyl-1-dihydro-1H-pyrazole-1-carboxamide

N- (4-Brotnphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-phenyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-raethyl-4- (2-chloroallyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Bromophenyl) -3- (4-chlorophenyl) -4-diethyl-4- (2-methylthioethyl) -4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Broraphenyl) -3- (4-chlorophenyl) -4-methyl-4- (3-cyanopropyl) -4,5-dihydro-iH-pyrazole-1-carboxamide

N- (4-Bromophenyl) _r 3- (4-chlorophenyl) -4-raethyl-4- (4-chlorophenyl) .beta., S-dihydro-1H-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-methyl-4- (4-difluoromethoxyphenyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-methyl-4- (4-trifluoromethoxyphenyl) -4,5-dihydro-lH-pyra2ol-l-carboxaraid

N- (4-bromophenyl) -3- (4-chlorophenyl) ~ 4-methyl-4- (4-trifluoromethylphenyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-ßromphenyl) -3- (4-chlorophenyl) -4-methyl-4-acetyl-4,5-dihydro ~ lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-methyl-4-allyl-4,5-dihydro-lH-pyrazole-1-carboxamide

M- (4-bromophenyl) -3- (4-chlorophenyl) -4-raethyl-4-benzyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (4-chlorphsnyl) -4-methyl-4-carbomethoxy-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-methyl-4-ethyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-Bromophenyl) -3- (4-chlorophenyl) -4-methyl-4-methallyl-4 _# 5-dihydro-1H-pyrazole-1-carboxamide

N- (4-3romphenyl) -3- (4-chlorophenyl) -4-methyl-4-methoxymethyl-4, S-dihydro-lH-pyrazol-l-carboxaraid

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-methyl-4-methylthioraethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-3romphenyl) -3- (4-chlorophenyl) -4-methyl-4-phenyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-Brornphenyl) -3- (4-chlorophenyl) -4-phenyl-4- (2-chloroallyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-phenyl-4- (2-methylthioethyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Broraphenyl) -3- (4-chlorophenyl) -4-phenyl-4- (3-cyanopropyl) 4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4 ~ Bromophenyl) -3- (4-chlorophenyl) ~ 4-phenyl-4- (4-chlorophenyl) 4 _f S-dihydro-lH-pyrazol-l-carboxainid

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-phenyl-4- (4-difluoromethoxyphenyl) -4, S-dihydro-lH-pyrazol-l-carboxamide

N - (4-Broraphenyl) -3- (4-chlorophenyl) -4-phenyl-4- (4-trifluoro-methoxyphenyl) -4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4_Bromphenyl) -3- (4-chlDrphenyl) -4-phenyl-4- (4-trifluoromethylphenyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Biphenyl) -3- (4-chlorophenyl) -4-phenyl-4-a'cetyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-phenyl-4-allyl-4,5-dihydrp-lH-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (4-chloro-phenyl.) - 4-phenyl-4 ~ benzy1-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-phenyl-carbohene-thoxy-4, B-dihydro-1H-pyrazole-1-carboxaraid

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-phenyl-4-ethyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-phenyl-4-methallyl-4,5-dihydro-lH-pyrazol-l-carboxamide

fsj- (4-BrQmphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methoxymethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-phenyl-4-tnethyl-4,5-dihydro-lH-pyrazole-1-carboxamide

M -. (4-bromophenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-N- (2-methoxyethylsulfenyl) -4,5-dihydro-lH-pyra2ol-l-carboxatnid

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-phenyl-4-raethyl-N- (2-nitrophenylsulfenyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

H- (4-bromophenyl) -3- (4-chlorophenyl) -4-phenyl-4-raethyl-N-acetyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4 ^ phenyl-4-raethyl-N-carboethoxy-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-N-carbomethoxy ^ .S-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-phenyl-4-raethyl-iM-carbomethoxycarbonyl-4,5-dihydro-lH-pyrazole-I-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-N-carbomethoxy3ulfenyl-4,5-dihydro-lH-pyrazol-l-carboxaraid

N- (4-3romphenyl) -3-r (4-chlorpSTenyl) -4-phenyl-4-methyl-N-diraethylearbamoyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-3romphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-N-formyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-N-methoxyraethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-N-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-N-methylsulphenyl ^ .S-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-N-trifluoroacetyl-4, S-dihydro-lH-pyrazol-l-carboxamide

M- (4-bromophenyl) -3- (4-chlorophenyl) ^ - phenyl ^ -methylthiomethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

M- (4-Broraphenyl) -3- (4-fluorophenyl) -R4-butyl-4-methyl-4,5-dihydro-lH-pyrazol-1-carboxaraid

N- (4-bromophenyl) -3- (4-fluorophenyl) -4-carbomethoxy-4-raethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3-phenyl-4-carbornethoxy-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-Carboethoxyphenyl) -3- (3-cblor-4-trifluoromethylphenyl) -4-caOHetoxy-4-methyl-4 _L 5-dihydro-1H-pyrazole-1-caΓ-carboxamide

U- (4-Carboethoxyphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Carboethoxyphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Carboisopropoxyphenyl) -3- (3-chloro-4-trifluorinethylphenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-Carboisopropoxyphenyl) -3- (3-chloro-4-trifluorinethylphenyl) of 4-carboethoxy-4-methyl-4 _f 5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Carboisopropoxyphenyl) -3- (3-chloro-4-trifluoroethylphenyl) 4-phenyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Carboisopropoxyphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (4-Carboisopropoxyphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxaraid

N- (4-Carboisopropoxyphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4 _f S-dihydro-lH-pyrazol-l-carboxamide

N- (4-Garbornethoxyphenyl) -3- {3-chloro-4-trifluoromethylphenyl) -. 4- (3-methylthiopropyl) -4-methyl-4 _f 5-dihydro-lH-pyrazol-lcarboxamid

N- (4-Carbornethoxyphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-raethyl-4, B-dihydro-lH-pyrazol-l-carboxamide

N- (4-carbomethoxyphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-4- _t, 5-dihydro-1H-pyrazole-1-carboxaraid

N- (4-Carbomethoxyphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Carbomethoxyphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Carbornethoxyphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-bromo-3-methyl-phenyl) -3- (4-chlorophenyl) -4-carbornethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Chiot-S-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (4_Chlorphenyl) -3- (3,4-dichlorophenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N -. (4-Ghlorphenyl) -3- (4-bromophenyl) -4-butyl-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

LSI (4-chlorophenyl) -3- (4-bromophenyl) -4-butyl-4-rnethyl-N- (lmethylethyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

M_ (4_Chlorphenyl) -3- (4-bromophenyl) -4-carbomethoxy-4-raethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N - (4-chlorophenyl) -3- (4-fluorophenyl) -4-butyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide .

N - (4-Ghlorphenyl) -3- (4-fluorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-chlorophenyl) -3- (4-methylphenyl) -4-carboroneethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-chlorophenyl) -3- (4-methoxyphenyl) -4-carbomethoxy-4-methyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (4-chlorophenyl) -3- (4-methylsulfonylphenyl) -4-carbornethoxy-4-methyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (4-chlorophenyl) -3- (4-methylthiophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-chlorophenyl) -3- (4-trifluoromethylphenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-chlorophenyl) -3-phenyl-4-carboethoxy-4-methyl-4 _f 5-dihydro-lH-pyrazole-1-carboxamide

N- (4_Chlorphenyl) -3-phenyl-4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-chlorophenyl) -3-phenyl-4-dimethylcärboxamido-4-methyl-4,5-dihydro-lH-pyrazbl-l-carboxamide

N- (4-chlorophenyl) -3-phenyl-N, 4-bis-carboraethoxy-4-methyl-4,5-dihydro-lH-pyra2ol-l-carboxamide

N- (4-chlorophenyl) -4-methyl-3,4-diphenyl-4,5-dihydro-lH-pyrazol-1-carboxatnid

N- (4-Difluoro-methoxyphenyl) -3- (3-chloro-4-trifluoro-ethyl-phenyl) -4- (3-methyl-thiopropyl) -4-methyl-4,5-dihydro-1H-pyrazole-1

carboxamide

N- (4-Difluoromethoxyphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-cahenoethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Difluoro-methoxyphenyl) -3- (3-chloro-4-trifluoroethylphenyl) -4-phenyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-difluoromethoxyphenyl) -3- (4-chlorophenyl) -4- (3-methylthxopropyl) -4-methyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (4-Difluoromethoxyphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4 _# 5-dihydro-1H-pyrazole-1-carboxamide

M- (4-Difluorinethoxyphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Dimethylaminoxyphenyl) -3- (4-chlorophenyl) -4-carbornethoxy-4-methyl-4 _f S-dihydro-lH-pyrazol-l-carboxamide

N- (4-Dimethylsulfonamidophenyl) -3- (3-chloro-4-trifluorinethyl-

phenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-dimethylsulfonamidophenyl) -3- (3-chloro-4-trifluorideethyl)

phenyl) -4-carboethoxy-4-methyl-4- _t, 5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Dimethylsulfonamidophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

H- (4-Dimethylsulfonamidophenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

JS *

N- (4-Dimethylsulfonamidophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-raethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-DimethyIsulfonamidophenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4,5 ~ dihydro-lH-pyrazol-l-carboxamide

N- (4-fluorophenyl) -3- (4-bromophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxaraid

N- (4-fluorophenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (4-fluorophenyl) -3- (4-fluorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-fluorophenyl) -3-phenyl-4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-Dodphenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-iH-pyrazol-l-carboxamide

N- (4-methoxyphenyl) -3- (4-chlorophenyl) -4-carbornethoxy-4-tnethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-methylphenyl) -3- (4-chlorophenyl) -4-carbornethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carbo.xamid

N- (4-M _e thylsulfonylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) · 4- (3-methylthiopropyl) -4-methyl-4 _f 5-dihydro-lH-pyrazole-1-carboxamide

N- (4-methylsulfonylphenyl) -3- (3-chloro-1-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-methylsulfonyl-phenyl) -3- (3-chloro-4-trifluoro-ethyl-phenyl) -4-phenyl-4-methyl-4,5-dihydro-1H-pyrazole-1-caΓ-carboxamide

Isi (4-methylsulfonylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N- (4-methylsulfonylphenyl) -3- (4-chlοrphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N- (4-methylsulfonylphenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-methylsulfonylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4 _# 5-dihydro-IH-pyrazole-1-carboxamide

N- (4-Methylsulfoxylphenyl) -3- (4-chlorophenyl) -4-carbornethoxy-4-methyl-4,5-dihydro-iH-pyrazol-l-carboxamide

N- (4-methylthiophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazol-1-carboxaraid

N- (4-methylthiophenyl) -3- (3-chloro «^ - trifluortnethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-methylthiophenyl) -3- (3-chloro-4-trifluorinethylphenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-methylthiophenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-raethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-methylthiophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-inethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-methylthiophenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dxhydro-lH-pyrazol-l-carboxamide

N- (4-methylthiophenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxainid

N- (4-Nitrophenyl) -3- (3-chloro-trifluoroethylphenyl) -4- (3-methylthiopropyl) -4-methyl-4, S-dihydro-1H-pyrazole-1-carboxamide

N- (4-nitrophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-nitrophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxaniid

N- (4-nitrophenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-nitrophenyl) -3- (4-chiοrphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-nitrophenyl) -3- (4-chlorophenyl) -4-carbornethoxy-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-nitrophenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazol-1-carboxatnid

N- (4-phenylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-4 B _{f-dihydro-lH-pyrazol-l-carboxamide}

N- (4-phenylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-trifluoromethoxyphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-rnethylthiopropyl) -4-methyl-4,5-dihydro-LH

pyrazole-1-carboxamide

N- (4-trifluoromethoxyphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-lcarboxamid

M- (4-trifluoromethoxyphenyl) -3- (3-chloro-4-trifluorinethylphenyl) -4-phenyl-4-raethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethoxyphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethoxyphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Trifluormethcxyphenyl) -3- (4-chlorophenyl) -4-carbo0iethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethoxyphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (Trimethylammoniumphenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamidjodid

N- (4-trifluoromethylphenyl) -3- (3-chloro-1-trifluoromethylphenyl) 4- (3-methylthiopropyl) -4-acetyl-4,5-dihydro-1H-pyrazole:

carboxaraid

N- (4-trifluoromethylphenyl) -3- (3-chloro ^ trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-carbomethoxy-4,5-dihydro-lH-pyrazole

1-carboxamide

M- (4-trifluorothyl-phenyl) -3- (3-chloro-tert-trifluoromethylphenyl) -

4- (3-raethylthiopropyl) -4-ethyl-4,5-dihydro-lH-pyra2ol-lcarboxamid

N- (4_Trifluorraethylphenyl) -3- (3-chloro-4-trifluorraethylphenyl) -4- (3-methylthiopropyl) -4-methyl-4,5-dihydro-lH-pyrazol-l-

carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-metiiylthiopropyl) -4-methyl-N- (2-methoxyethylsulfenyl) -

4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) 4- (3-methylthiopropyl) -4-methyl-N- (2-nitrophenylsulfenyl) -

4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) ·

4- (3-methylthiopropyl) -4-methyl-N-acetyl-4,5-dihydro-lH-pyräzol-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) · 4- (3-methylthiopropyl) -4-methyl-N-carboethoxy-4 _f 5-dihydro-LH

pyrazole-1-carboxamide

N- (4-trifluoroethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-methyl-N-carbomethoxy-4,5-dihydro-1H-pyrazole-1-carboxamide

N - (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) 4- (3-methylthiopropyl) -4-methyl-N-carbomethoxycarbonyl-4,5-

dihydro-lH-pyrazole-1-carboxamide

W- (4-trifluoroethylphenyl) -3- (3-chloro-4-trifluoro-ethylphenyl) 4- (3-methylthiopropyl) -4-methyl-N-carboniethoxysulfenyl-4,5-

dihydro-lH-pyrazole-1-carboxamide

N- (4-trifluorinatedethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) 4- (3-methylthiopropyl) -4-methyl-N-dimethylcarbamoyl-4,5-

dihydro-lH-pyrazole-1-carboxamide

M- (4-trifluoroethylphenyl) -3- (3-chloro-1-trifluoromethylphenyl) 4- (3-methylthiopropyl) -4-methyl-N-formyl-4,5-dihydro-1H

pyrazol-l-carboxaroid

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) 4- (3-methylthiopropyl) -4-methyl-N-methoxy-methyl-4,5-dihydro-

lH-pyrazol-1-carboxamide

N- (4-trifluoroethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) 4- (3-methylthiopropyl) -4-methyl-N-ethyl-4,5-dihydro-1H

pyrazol-i-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro ^ trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-methyl-N-methylsulphenyl-4,5-dihydro-

IH-pyrazole-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) 4- (3-methylthiopropyl) -4-methyl-N-trifluoroacetyl-4,5-dihydro-

IH-pyrazole-l-carboxamide

N- (4-trifluoroethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4- (2-chloroallyl) -4,5-dihydro-1H-pyra-2-ol

carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoro-ethylphenyl) -4-carboethoxy-4- (2-methylthioethyl) -4,5-dihydro-1H-pyrazole-1

carboxamide

N- (4-trifluorothylphenyl) -3- (3-chloro-trifluorinated phenyl) -4-carboethoxy-4- (3-cyanopropyl) -4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-1-trifluoromethylphenyl) -4-carboethoxy-4- (4-chlorophenyl) -4,5-dihydro-1H-pyrazole-1

carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-1-trifluoromethylphenyl) ·

4-carboethoxy-4- (4-difluoromethoxyphenyl) -4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4- (4-trifluorooctylthoxyphenyl) -4,5-dihydro-1-l-H-pyrazole-1-carboxamide

N- (4-trifluorothylphenyl) -3- (3-chloro-4-trifluoroolylthylphenyl) 4-carboethoxy-4- (4-trifluoromethylphenyl) -4,5-dihydro-IH-pyrazole-1-carboxamide

N- (4-trifluorothylphenyl) -3- (3-chloro-trifluoromethylphenyl) -4-carboethoxy-4-acetyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N- (4-trifluorothylphenyl) -3- (3-chloro-trifluoromethylphenyl) -4-carboethoxy-4-allyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-benzyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluorothylphenyl) -3- (3-chloro-trifluoromethyl-phenyl) -4-carboethoxy-4-carboethethoxy-4,5-dihydro-IH-pyrazole-1-carboxamide

-τ SV "1

N- (4-trifluoromethylphenyl) -3- (3-chloro-1-trifluoromethyl-phenyl) -4-carboethoxy-4-ethyl-4, S-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro) -trifluorinated phenyl) 4-carboethoxy-4-methallyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluorinated phenyl) -3- (3-chloro-4-trifluoroethylphenyl) 4-carboethoxy-4-methoxymethyl-4,5-dihydro-1H-pyrazole · l-

carboxamide

N- (4-trifluoromethylphenyl) -3- (3-trifluoromethylphenyl Chiot ^) - ^x j -.- 4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-Chiot ^ trifluoromethylphenyl) -4-carboethoxy-4-methyl-N- (2-methoxyethylsulfenyl) -4,5-dihydro-IH-.pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-N- (2-nitrophenylsulfenyl) -4,5-dihydrolH-pyrazole-1-carboxamide -

N- (4-trifluoromethylphenyl) -3- (3-chloro-1-trifluoromethyl-phenyl) -4-carboethoxy-4-methyl-N-acetyl-4,5-dihydro-1H-pyrazole-1

carboxamide

N- (4-trifluoromethylphenyl) -3- (3-trifluoromethylphenyl Chiot ^) of 4-carboethoxy-4-methyl-N-carboethoxy-4 _ί 5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro ^ trifluoromethylphenyl) -4-carboethoxy-4-methyl-N-carbomethoxy-4,5-dihydro-lH-pyrazole

1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-N-carbomethoxycarbonyl-4,5-dihydro-: LH

pyrazole-1-carboxamide

N- (4-trifluorothyl-phenyl) -3- (3-chloro-trifluorinated-phenyl) -carboethoxy-methyl-N-carboroneethoxysulfenyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-Chiot - ^ - trifluoromethylphenyl) -4-carboethoxy-4-methyl-N-dimethylcarbamoyl-4 ₁ 5-dihydro-LH

pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro · ^ trifluoromethylphenyl) -4-carboethoxy-4-methyl-N-formyl-4,5-dihydro-lH ~ pyrazole: L-

carboxamide "

N- (4-Trifluorraethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-N-methoxymethyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-N-methyl-4,5-dihydro-lH-pyrazol-l-carbox ·

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-raethyl-N-methylsulphenyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -

4-carboethoxy-4-methyl-N-trifluoroacetyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluormethy! Phenyl) -4-carfaoethoxy-4-methylthiomethyl-4,5-dihydro-lH-pyrazol-lcarboxamid

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-phenyl-4,5-dihydro-lH-pyrazol-l-carboxaraid

N- (4-trifluorothylphenyl) -3- (S-chloro-S-trifluoromethylphenyl) -4-methyl-4- (2-chloroallyl) -4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (S-chloro-1-trifluoromethylphenyl) -4-methyl-4- (2-methylthioethyl) -4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-1-trifluoromethyl-phenyl) -4-methyl-4- (3-cyanopropyl) -4 _> 5-dihydro-1H-pyrazole-1-carboxamide

j- (4-trifluoromethylphenyl) -3- (3-Chiot ^ trifluoromethylphenyl) -4-methyl-4- (4-chlorophenyl) -4,5-dihydro-lH-pyrazol-l-carboxafnid

N- (4-trifluoromethylphenyl) -3- (3-Chiot ^ trifluoromethylphenyl) -4-methyl-4- (4-difluorinethoxyphenyl) -4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-methyl-4- (4-trifluoromethoxyphenyl) -4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-Trifluorraethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-methyl-4- (4-trifluoromethylphenyl) -4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-fnethyl-4-acetyl-4,5-dihydro-lH-pyrazol-l-carboxaraid

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-methyl-4-allyl-4 _# 5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-methyl-4-benzyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-methyl-4-carbornethoxy-4,5-dihydro-IH-pyrazole-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-1-trifluoromethyl-phenyl) -4-methyl-4-ethyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-A-trifluoromethylphenyl) -4-methyl-4-methallyl-4, S-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-1-trifluoromethyl-phenyl) -4-methyl-4-methoxymethyl-4, S-dihydro-1H-pyrazole-1-carboxamide

Ν_ (4-trifluoromethylphenyl) -3- (3-chloro-1-trifluoromethylphenyl) -methyl-methylthiomethyl-1-dihydro-1H-pyrazole-1-carboxamide

U- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-methyl-4-phenyl-4, S-dihydro-1H-pyrazole-1-carboxamide

M- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4- (2-chloroallyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4- (2-methylthioethyl) -4,5-dihydro-lH-pyrazol-lcarboxamid

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4- (3-cyanopropyl) -4 _i 5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4- (4-chlorophenyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4- (4-difluoromethoxyphenyl) -4,5-dihydro-lH-pyrazol-lcarboxamid

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4- (4-trifluorraethoxyphenyl) -4,5-dihydro-lH-pyrazol-lcarboxamid

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4- (4-trifluörmethylphenyl) -4,5-dihydro-IH-pyrazol-lcarboxamid

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-acetyl-4 _f S-dihydro-lH-pyrazol-l-carboxamide *

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluorinethylphenyl) -4-phenyl-4-allyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoroethylphenyl) -4-phenyl-4-benzyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-carbomethoxy-4,5-dihydro-1H-pyrazole-1-carboxamide

Ν- (4-trifluoroethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-ethyl-4,5-dihydro-1H-pyrazole-1-carboxamide

M- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) 4-phenyl-4-methallyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-1-trifluoromethylphenyl) -4-phenyl-4-methoxymethyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) 4-phenyl-4-methyl-4, S-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-N- (2-methoxyethylsulfenyl) -4,5-dihydro-IH-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-N- (2-nitrophenylsulfenyl) -4,5-dihydro-1H-

pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (S-chloro- ₁ -trifluoromethylphenyl) -4-phenyl-4-methyl- ^] -acetyl-4,1-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-Chiot ^ trifluoromethylphenyl) -4-phenyl-4-methyl-N-carboethoxy-4,5-dihydro-lH-pyrazol-l-

carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro ^ trifluoromethylphenyl) -4-phenyl-4-methyl-N-carbornethoxy-4,5-dihydro-lH-pyrazole-1-carboxamide

j N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-N-carboroneethoxycarbonyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N- (4-Trifluorraethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-N-carbomethoxysulfenyl-4,5 ^ dihydro-lH-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-N-dimethylcarbamoyl-4,5-dihydro-lH-paryzol-

1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) - ^J 4-phenyl-4-methyl-N-foΓmyl-4,5-dihydΓO-lH-pyΓazol l caΓboxamid

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-N-methoxymethyl-4,5-dihydro-lH-pyrazol-lcarboxamid

N_ (4-trifluoromethylphenyl) -3- (3 ~ chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-N-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-N-methylsulphenyl-4,5-dihydro-lH-pyrazol-lcarboxamid

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluorinethylphenyl) -4-phenyl-4-methyl-N-trifluoroacetyl-4,5-dihydro-lH-pyrazol-l-

carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -1-phenyl-1'-methylthiomethyl-1, S-dihydro-1H-pyrazole-1-carboxamide

N- (4-Trifluorinethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-acetyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoroethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-carboroneethoxy-4 _# 5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Trifluorraethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-ethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-3 "fluoromethylphenyl) -Z- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4, S-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-N- (2-methoxyethylsulfenyl) -4,5-dihydro-LH

pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl-4-methyl-N- (2-nitrophenylsulfenyl) -4 _# 5-dihydro-1H-

pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-N-acetyl-4 _f 5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-N-carboethoxy-4,5-dihydro-lH-pyrazol-lcarboxamid

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-N-carbomethoxy-4,5-dihydro-lH-pyrazol-l-

carboxamide

M - (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-N-carboroneethoxycarbonyl-4 _# 5-dihydro-IH-pyrazole-1-carboxamide

N -. (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4- (3-methyIthio-

propylJ ^ -methyl ^ .S-N-carbomethoxysulfenyl-dihydro-lH-pyrazol-l-carboxatnid

M- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropylJ ^ -methyl-N-dimethylcarbamoyl ^ .S-dihydro-lH-pyrazole

1-carboxamide

N -. (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4- (3-raethylthiopropyl) -4-raethyl-N-formyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N -. (4_Trifluormethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-N-methoxymethyl-4,5 ~ dihydro-lH-pyrazol-l-

carboxaraid

N- (4-Trifluortnethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-N-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-N-methylsulphenyl ^ .S-dihydro-lH-pyrazol-lcarboxamid

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-ethyl-N-trifluoroacetyl-4 _, 5-dihydro-1H-pyrazole-1

carboxamide

N- (4-Trifluorraethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-

(2-chloroallyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (2-methylthioethyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Trifluorinethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (3-cyanopropyl) -4, S-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (4-chlorophenyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (4-difluorraethoxyphenyl) -4,5-dihydro-lH-pyra2ol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (4-trifluoromethoxyphenyl) -4,5-dihydro-lH-pyrazol-l-carboxainid

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (4-trifluorinethylphenyl) -4,5-dxhydro-IH-pyrazol-l-carboxaraid

N- (4-Trifluorinethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-acetyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-allyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Trifluorinethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-benzyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Trifluorraethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-carbomethoxy ^ jS-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-ethyl ^^ - dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methallyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methoxymethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydrp-lH-pyrazole: L-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N- (2-methoxyethylsulfenyl) -4,5-dihydro-lH-pyrazole: l-

carboxamide

Ν- (4-Trifluorinethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-raethyl-N- (2-nitrophenylsulfenyl) -4,5-dihydro-lH-pyrazol-l-

carboxamide

IM- (4-Trifluorraethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-roethyl-N-acetyl-4,5-dihydro-lH-pyra2ol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-carboethoxy-4,5-dihydro-lH-pyrazol-l-carboxajnid

^ 4- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-carboinethoxy ^ .S-dihydro-lH-pyrazol-l-carboxatnid

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-

methyl-N-caΓbomethoxycaphenyl-4 _# 5-dihydΓO-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-isl-carborne thoxysulf enyl-4,5-dihydro-1H-pyrazole-1-carboxamide

H- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-dimethylcarbamoyl-.S-dihydro-1H-pyrazole-1-carboxarax

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-forrayl-4 _J 5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Trifluorinethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-methoxymethyl ^ .S-dihydro-iH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-raethyl-4,5-dihydro-lH-pyrazol-l-carboxaraid

N- (4-Trifluortnethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-methylsulphenyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (4-Trifluorinethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-trifluora, cetyl-4,5-dihydro-lH-pyra2ol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4 -., Methylthioethyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-phenyl ^ iS-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-dimethylcarbamo "yl-4-methyl-4 _f S-dihydro-lH-pyrazol-i-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-methyl-4- (2-chloroallyl) -4,5-dihydro-lH-pyrazol-l-carboxamide,

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-methyl-4- (2-methylthioethyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-methyl-4- (3-cyanopropyl) -4,5-dihydro-iH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-methy1-4- (4-chlorophenyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-methyl-4- (4-difluoromethoxyphenyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylsulfinyl) -3- (4-chlorophenyl) -4-methyl-4- (4-trifluoromethoxyphenyl) -4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-methyl-4- ( A- trifluoromethyphenyl) -4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-methyl-4-acetyl-4 _# 5-dihydro-1H-pyrazole-1-carboxamide

, N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-methyl-4-allyl - ^ S-dihydro-lH-pyrazol-l-carboxamide.

N- (4-Trifluormethyphenyl) -3- (4-chlorophenyl) -4-methyl-4-benzyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Trifluortnethylphenyl) -3- (4-chlorophenyl) -4-methyl-4-carbomethoxy-4,5-dihydro-lH-pyrazol-l-carboxainid

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-methyl-4-ethyl ^ .S-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-methyl-4-methallyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-methyl-4-methoxymethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Trifluorraethylphenyl) -3- (4-chlorophenyl) -4-methyl-4-methylthiomethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-methyl-4-phenyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4- (2-chloroallyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4- (2-methylthioethyl) -4,5-dihydro-LH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4- (3-cyanopropyl) -4, S-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4- (4-chlorophenyl) -4,5-dihydro-lH-pyrazol-l-carboxainid

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4- (4-difluoromethoxyphenyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4- (4-trifluoromethoxyphenyl) -4,5-dihydro-lH-pyrazol-l-carboxaraid

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4- (4-trifluoromethylphenyl) -4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-acetyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-allyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-benzyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-carbornethoxy-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-ethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methallyl-4 _# 5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methoxymethyl-4,5-dihydro-lH-pyra2ol-l-carboxamide

N- (4-Trifluorinethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4,5-dihydro-LH-pyrazol-l-carboxafflid

M- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-

methyl-N- (2-methoxyethylsulfenyl) -4,5-dihydro-lH-pyrazol-l ·

carboxaraid

Ν- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-

raethyl-N- (2-nitrophenylsulfenyl) -4,5-dihydro-lH-pyrazol-l-

carboxamide

{G- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-tnethyl-N-acetyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-raethyl-N-carboethoxy-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-N-carbomethoxy-4 _# 5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-N-carbomethoxycarbonyl ^ .S-dihydro-lH-pyrazol-l-

carboxaraid

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-N-carbomethoxysulfenyl-4,5-dihydro-lH-pyrazol-l-

carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-N-dimethylcarbamoyl-4,5-dihydro-lH-pyrazol-l-

carboxamide

N- (4-T rif luorme thylphenyl) 3- (4-chlorophenyl) -4-phenyl-4-methyl-N-forrayl-4,5-dihydro-1H-pyrazol-1-carboxaraid

N- (4-trifluoroethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-N-methoxymethyl-4 _L 5-dihydro-1H-pyrazole-1-carboxamide

M- (4-.Trifluormethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-N-methyl ^ .S-dihydro-lH-pyrazol-l-carboxamide

N -. (4_Trifluormethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-N-methylsulphenyl-4,5-dihydro-lH-pyra2ol-l-carbox.amid

N. (4-trifluorothylthylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-N-trifluoroacetyl ^^ S-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-ΠJethylthiomethyl-4 _J-5 dihydΓO-lH-pyΓa2ol l caΓboxaπlid

N- (4-Trifluorraethylphenyl) -3-phenyl-4-carboethoxy-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3-phenyl-4-carboraethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3-phenyl-4-dimethylcarbamoyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N-phenyl-3- (3-chloro-4-trifluoroethylphenyl) -A- (3-methylthiopropyl) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N-phenyl-3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-ethyl-4,5-dihydro-1H-pyrazole-1-carboxamide.

N-phenyl-3- (3-chloro-4-trxfluormethylphenyl) -4-phenyl-4-methyl ^ jS-dihydro-lH-pyrazol-l-carboxatnid

2 4 18

N-phenyl-3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4, 5-dihydro-lH-pyrazol-l-carboxatnid

N-phenyl-3- (4-chlorophenyl} -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N-phenyl-3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N-phenyl-3- (4-chlorophenyl) -4-phenyl-4-tnethyl-4,5-dihydro-IH-pyrazole-l-carboxamide

Group B

M- (3,4-dichlorophenyl) -3- (4-chlorophenyl) -4-carbornethoxy-4-methyl-4,5-dihydro-lH-pyrazole

N- (3,4-Dibhlorophenyl) -3-phenyl-4-carbomethoxy-4-methyl-4 _J 5-dihydro-1H-pyrazole-1-carboxamide

N, 3-bis (4-bromophenyl) -4-carbomethoxy-4-methyl-4,5-dihydrolH-pyrazole-1-carboxamide

N, 3-bis ~ (4-chlorophenyl) -4- (4-chlorobenzoyl) -4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-acetyl-4-methyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-acetyl-4-phenyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-benzoyl-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbo (2-dimethylaminoethoxy) -4-methyl-4 _f S-dihydro-lH-pyrazol-l-carboxamide

N _# 3-bis (4-chlorophenyl) -4-carbo (2-dimethylaminoethoxy) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide hydrochloride salt

N, 3-bis (4-chlorophenyl) -4-carbo (2-methylsulfonylethoxy) -4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbo (2-methylthioethoxy) -4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbobutoxy-4-methyl-4,5-dihydro-IH-pyrazol-l-carboxaraid

N, 3-bis (4-chlorophenyl) -4-carboet.hoxy-4,5-dihydro.-lHTPyrazol-1-carboxamide

N, 3-3is (4-chlorophenyl) -4-carboethoxy-4-methyl-4 _, 5-dihydrolH-pyrazole-1-carboxamide

N, 3-3is (4-chlorophenyl) -4-carboisopropoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbomethyloxy-4-methyl-4,5-dihydrolH-pyrazol-l-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbornethoxy-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbomethoxy-4-ethyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbornethoxy-4-methy1-4,5-dihydro-IH-pyrazole-1-carboxamide

N, 3-bis- (4-chlorophenyl) -4-carboroneethoxy-4-methyl-4,5-dihydro-IH-pyrazole-1-carboxthioamide

N, 3-bis (4-chlorophenyl) -4-carbotnethoxy-4-methyl-N-acetyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbornethoxy-4-phenyl-4,5-dihydro-IH-pyrazol-l-carboxatnid

N , 3-bis (4-chlorophenyl) -4-carboroneethoxy-N, 4-dimethyl-4,5-dihydro-1H-pyrazole-1-carboxamide

^f N, 3-Bis (4-chlorophenyl) -4-carbomethoxy-N- (1-carbomethoxy-prop-2-yl-thio) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-carboroethoxy-N- (2-nitrophenylsulfenyl) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N , 3-bis (4-chlorophenyl) -4-carbomethoxy-N- (3-cyanopropylthio) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbomethoxy-N-acetyl-4-Riethyl-4,5-dihydro-lH-pyrazol-l-carboxthioamid

N, 3-bis (4-chlorophenyl) -4-carbomethoxy-N-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxaraid

N, 3-bis (4-chlorophenyl) -4-carbornethoxy-N-carbornethoxythio-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbornethoxy-N-carbophenoxy-4-methy1-4,5-dihydro-lH-pyrazol-l-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbornethoxy-N-carbovinyloxy-4-methyl-4,5-dihydro-lH ~ pyrazol-l-carboxamide

N, _J 3-Bis- (4-chlorophenyl) -4-carbomethoxy-N-dimethylcarbamoyl-4-methyl-4, ^ -dihydro-1H-pyrazole-1-carboxaraid

N.S.-bis-i ^ ^ chlorphenylJ -carboniethoxy-N-formyl ^ -methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N _< 3-bis (4-chlorophenyl) -4-carborethoxy-N-methoxymethyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N _# 3-bis (4-chlorophenyl) -4-carbomethoxy-N-methyloxallyl-4-methyl ^ f S -dihydro-1H-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbomethoxy-N-methyl-4-tnethylthio

4,5-dihydro-lH-pyrazol-l-carboxamide

N _# 3-bis (4-chlorophenyl) -4-carbomethoxy-N-phenylthio-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbomethoxy-N-propylthio-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-carboraethoxy-N-trifluoracetyI-4-methyl-4,5-dihydro-iH-pyrazol-l-carboxamide

N, 3-bis (4-chlorophenyl) -4-carbomethylthiomethoxy-4-methyl-4,5-dihydro-lH-pyrazol ^ l-carboxaraid

N, 3-bis (4-chlorophenyl) -4-carbopropoxy-4-methyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N _t 3-bis (4-chlorophenyl) -4-carboxy-4,5-dihydro-1H-pyrazole-1-carboxamide

N _f 3-bis (4-chlorophenyl) -4-carboxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N _f 3-Bis (4-chlorophenyl) -4-carboxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide sodium salt

N _# 3-bis (4-chlorophenyl) -4-carboxy-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-diethylcarboxamido-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-dimethylcarbamoyl-4, 5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-dimethylcarboxamido-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N, 3-bis (4 ^ chlorophenyl) -4-dimethylthiocarbamoyl-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N, 3-bis (4-chlorophenyl) -4-isobutyryl-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-methylthiothiocarbonyl-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N, 3-bis (4-chlorophenyl) -4-pivaloyl-4-methyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-propionyl-4-methyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N, 3-bis (4-trifluoromethylphenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N- (1-Naphthy1) -3- (4-chlorophenyl) -4-carbornethoxy-4,5-dihydro-IH-pyrazole-l-carboxamide

N- (2,4-Dxnitrophenyl) -3- (4-chlorophenyl) -4-carbornethoxy-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (2-fluoro-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dxhydro-lH-pyrazole-1-carboxamide

N- (2-fluoro-4-trifluorinethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-raethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

λ N- (2-methyl-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoroethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (2-methyl-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4, S-dihydror-1H-pyrazole-1-carboxamide

N- (3-Bromo-4-trifluorinated phenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-bromo-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4, S-dihydro-lH-pyrazol-l-carboxamxd

N- (3-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carbo-ethoxy-4-methyl-4,5-dxhydro-1H-pyrazole-1-carboxamide

Isi (3-bromophenyl) -3- (4-chlorophenyl) -4-carbatoethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxaraid

N- (3-carboethoxyphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxaraxd

N- (3-carboethoxyphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl ^^ - dihydro-lH-pyrazol-l-carboxamide

N- (3-Carboisopropoxyphenyl) -3- (S-chloro-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-Carboisopropoxyphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4rraethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3 ~ carbomethoxyphenyl) -3- (3-trifluoromethylphenyl Chiot ^) of 4-carboethoxy-4-methyl-4 _f S-dihydro-lH-pyrazol-l-carboxamide

M- (3-Carboraethoxyphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxaraid

N- (3-GhIoTl-trifluoromethylphenyl) -3- (3-chloro-trifluoromethylphenyl) -4-carboethoxyhoxy-1-methyl-, 5-dihydro-1H-pyrazole-1-carboxamide

N- (3-chloro-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-chlorophenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide ,

N- (3-cyano-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N- (S-Cyano ^ trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (3-difluoromethoxy-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N- (3-Difluoromethoxy-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-difluoromethoxyphenyl) -3- (3-chloro-4-trifluoromethylphenyl) - _; 4-carboethoxy-4-methyl-4, S-dihydro-lH-pyrazol-l-carboxamide

fsl- (3-Difluoromethoxyphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-1S-dihydro-1H-pyrazole-1-carboxamicl

N- (3-Dimethylsulfona (nidophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-

carboxamide

N- (3-dimethylsulfonamidophenyl) -3- (4-chlorophenyl) -4-carbo- "" ethoxy-4-methyl-4,5-dihydrolo-1H-pyrazole-1-caΓ-carboxamide

N- (3-fluoro-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-

carboxamide

N- (3-fluoro-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-methoxy-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluorinated phenyl) -4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-methoxy-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4, S-dihydro-lH-pyrazol-l-carboxaraid

N- (3-methyl-4-trifluoromethylphenyl) -3- (3-Chiot ^ trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazole. 1-carboxamide

N- (3-methyl-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N_ (3-methylthiophenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl ^ jS-dihydro-lH-pyrazol-l-carboxatnid

N- (3-methylsulfonyl-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-IH-pyrazole-1-carboxamide,

N- (3-methylsulfonyl-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-methylsulfonylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-methylsulfonylphenyl) -3- (4-chlorphertyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxaraid

N- (3-methylsulfonylphenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydrd-lH-pyrazol-l-carboxamide

N- (3-methylthio-4-trifluoroethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxaride

H- (3-methylthio-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3-methylthiophenyl) -3- (3-chloro-4-trifluorinethylphenyl) -4-caΓboethoxy-4-raethyl-4,5-dihydΓO-lH-pyΓazol l caΓboxamid

TM (3-methylthiophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-nitro-4-trifluorinethylphenyl) -3- (3-chloro-4-trifluoro

methylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-1-carboxaraid

N- (3-nitro-4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4 ~ methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-trifluoroethoxy-4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethyl-phenyl) -4-carboethoxy-4-methyl-4 _# 5-dihydro-1H-pyrazole-1-carboxamide.

N- (3-trifluoromethoxy-4-trifluorraethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydΓo-lH-pyΓa2ol-l-carboxamide

~ \ N- (3-Trifluorinethoxyphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4 _Jr 5-dihydro-lH-pyrazol-l-carboxamide

N- (3-trifluoromethoxyphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4 _f 5-dihydro-lH-pyrazol-l-carboxamide

N- (3-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4 _ί 5-dihydro-lH-pyrazol-l-carboxamide

N- (3-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (3-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carbornethoxy- ^ 4-methyl-4 ₄ 5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromo-3-methylphenyl) -3- (4-chlorophenyl) -4-carbornethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluorraethylphenyl) -4- (3-methylthiopropyl) -4-acetyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-carbomethoxy-4,5-dihydro-lH-pyrazol-l-

carboxamide

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy ^ - ^ - chloroallylJ ^ jB-dihydro-1H-pyrazole-1-carboxamide

N- (4-Bromophenyl) -3- (S-chloro-trifluorinated phenyl) -4-carboethoxy-4- (2-methylthioethyl) -4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Bromophenyl) -3- (3-chloro) -trifluorinated phenyl) -4-carboethoxy-4- (3-cyanopropyl) -4,5-dihydro-1H-pyrazole-1-carboxamide

_s N- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4- (4-chlorophenyl) -4 _i 5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoroethylphenyl) -4-carboethoxy-4- (4-difluoroethoxyphenyl) -4,5-dihydro-IH-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4- (4-trifluoromethoxyphenyl) -4, 5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4- (4-trifluoromethylphenyl) -4,5-dihydro-lH-pyrazol-1-carboxatnid

N- (4-Broraphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-acetyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (3-chloro-1-trifluoromethyl-phenyl) -4-carboethoxy-4-allyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-benzyl-4,5-dihydro-IH-pyrazole-1-carboxamide

fe -τ I

M- (4-Borraphenyl) -3- (3-chloro-4-trifluoroethylphenyl) -4-carboethoxy-4-carbomethoxy-4 _# 5-dihydro-1H-pyra-2-ol-1-carboxamide

M- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-ethyl-4,5-dihydro-1H-pyrazole-1-carboxamide

fsi- (4-bromo-phenyl) -3- (3-chloro-P 1 -trifluoromethylphenyl) -4-ca rboethoxy-4-methallyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Broraphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methoxymethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromo-phenyl) -3- (3-chloro-trifluoromethylphenyl) -4-chloroethoxy-methyl-f, dihydro-1H-pyrazole-1-carboxaraid

N- (4-Brotnphenyl) -3- (3-chlοr-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-N- (2-raethoxyethylsulfenyl) -4,5-dihydro-LH

pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-tnethyl-N- (2-nitrophenylsulfenyl) -4,5-dihydro-LH

pyrazole-1-carboxamide

N- (4-3romphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-N-acetyl-4,5-dihydΓo-lH-pyΓazol l caΓboxamid

N- (4-3romphenyl) -3- (3-chloro-4-trifluorraethylphenyl) -4-carboethoxy-4-methyl - ^^ _{l-caΓboethoxy-4/5} dihydΓO-lH-pyΓazol-l-

carboxamide

N- (4-Broraphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy ^ -methyl-N-carbomethoxy ^ jS-dihydro-lH-pyrazol-l-

 carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluorinethylphenyl) -4-carbo-

ethoxy ^ -methyl ^ .S-N-carbomethoxycarbonyl-dihydro-lH-pyrazole-1-carboxamide

N- (4-Bromophenyl) -3- (3-chloro-trifluoromethylphenyl) -4-carboethoxy-4-methyl-N-carboroneethoxy-sulfenyl-4 _# 5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-N-dimethylcarbamoyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluorraethylphenyl) -4-carboethoxy-4-methyl-N-formyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluorinethylphenyl) -4-carboe.thoxy-4-methyl-N-methoxymethyl-4,5-dihydro-lH-pyrazol-l-

carboxamide

N- (4-bromophenyl) -3- (3-Chiot ^ trifluoromethylphenyl) -4-carboethoxy-4-methyl-N-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (3-c-silyl-4-trifluoromethylphenyl) -4-carbo-ethoxy-4-methyl-N-methylsulfenyl-4,5-dihydro-1H-pyrazole-1-carboxamide.

N- (4-bromophenyl) -3- (3-Chiot ^ -trifluorraethylphenyl) -4-carboethoxy-4-methyl-N-trifluoroacetyl-4,5-dihydro-lH-pyrazol-l-

carboxamide

N- (4-Broraphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methylthiomethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-phenyl-4,5-dihydro-lH-pyrazol-i-carboxamide

· - 93 -

N- (4-Bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-methyl-4-acetyl-4,5-dihydro-1H-pyrazole-1-carboxamide

tis (4-bromophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-methyl-4-carbomethoxy-4, S-dihydro-1H-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (3-chloro) -trifluorophenyl) -4-phenyl-4-acetyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Bromophenyl) -3- (3-chloro-1-trifluoromethyl-phenyl) -4-phenyl-4-carbomethoxy-4 _/ 5-dihydro-1H-pyrazole-1-carboxaraid

N- (4-bromophenyl) -3- (4-chlorophenyl) -4- (3-methylth: iopropyl) -4-acetyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Bromophenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-carbomethoxy-4 _# 5-dihydro-1H-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (2-chloroallyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (2-methylthioethyl) -4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (3-cyanopropyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (4-chlorophenyl) -4,5-dihydro-IH-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (4-difluoromethoxyphenyl) -4,5-dihydro-lH-pyrä-zol-1-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (4-trifluormethoxyphqnyl) -4,5-dihydro-IH-pyrazole-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (4-trifluoromethylphenyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-acetyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-ailyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-benzyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-3romphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-carbomethoxy-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carhoethoxy-4-ethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methallyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -R3- (4-chlorophenyl) -4-carboethoxy-4-methoxymethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-8-rophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N- (2-methoxyethylsulfenyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N- (2-nitrophenylsulfenyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-acetyl ^ jS-dihydro-lH-pyrazol-l-carboxamide

N- (4-Bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-carboethoxy-4 _# 5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Broraphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-carbomethoxy ^ jS-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-carbomethoxycarbonyl ^ jS-dihydro-lH-pyrazol-l-carboxamide

N- (4-Bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-carboroneethoxysulfenyl-4 _/ 5-dihydro-1H-pyrazol-1-carboxamide

O '

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-dimethylcarbamoyl ^ jS-dihydro-lH-pyrazol-l-carboxamide

N- (4-Bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-formyl-4,5-dihydro-1H-pyrazole-1-carboxamide ^Λ

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-methoxymethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-methyl-4,5-dihydro-lH-pyrazole: L-carboxamide

'' - i'J N - (4-3romphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-methylsulfenyl-4 _# 5-dihydro-IH-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carhoethoxy-4-methyl-N-trifluoroacetyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methylthiomethyl-4, S-dihydro-1H-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-phenyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-carbornethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-methyl-4-acetyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-Bromophenyl) -3- (4-chlorophenyl) -4-methyl-4-carbomethoxy- 4, S-dihydro-1H-pyrazole-1-carboxamide

N- (4-Broraphenyl) -3- (4-chlorophenyl) -4-phenyl-4-acetyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-phenyl-4-carbomethoxy-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3- (4-fluorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-bromophenyl) -3-phenyl-4-carbomethoxy-4-raethyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-carboethoxyphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-carboethoxyphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Carboethoxyphenyl) -3- (4-chlorophenyl) -4-carbomethoxy- 4, 5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Carboisopropoxyphenyl) -3- (3-chloro-4-trifluoromethylphenyl) 4- (3-methylthiopropyl) -4-methyl-4 _J 5-dihydro-1H-pyrazole-1

carboxaniid

- 97 -

N- (4-Carboisopropoxyphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-LH-pyrazole-1-carboxamide

N - (4-Carboisopropoxyphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

| N] - (4-Carboisopropoxyphenyl) -3- (4-chlorophenyl) -4- (3-methylthioprQpyl) -4-methyl-4 _J-5 dihydror-lH-pyrazol-l-carboxamide

N- (4-Carboisopropoxyphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxaraid

N- (4-Carboisopropoxyphenyl) -3- (4-chlorophenyl) -4-phenyl-4-niethyl ^ jS-dihydro-lH-pyrazol-l-carboxaraid

N- (4-carbomethoxyphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4- (3-methylthiopropyl) -4-methyl- A, 5-dihydro-1H-pyrazole-1-carboxamide

N- (4-carbomethoxyphenyl) -3- (3-chloro-4-1-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-carbomethoxyphenyl) -3- (3-chloro-trifluorothylphenyl) -4-phenyl-4-methyl-4,5-dxhydro-1H-pyrazole-1-carboxamide

N- (4-Carbomethoxyphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-methyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (4-Carbomethoxyphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Carbomethoxyphenyl) -3- (4-chlorophenyl) -4-carbornethoxy-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Garbomethoxyphenyl) -3- (4-chlorophenyl) -4-phenyl-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-chloro-3-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyra2ol-l-carboxamide

N- (4-chlorophenyl) -3- (4-bromophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-chlorophenyl) -3- (4-fluorophenyl) -4-carbomethoxy-4-methyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (4-.Chlorphenyl) -3- (4-methoxyphenyl) -4-carbomethoxy-4-methyl-

4,5-dihydro-lH-pyrazol ^ l-carboxamide

N- (4-chlorophenyl) -3- (4-methylphenyl) -4-carbornethoxy-4-methyl-4, 5-dihydno-lH-pyrazol-l-carboxamide

N- (4-Chloro-phenyl) -3- (4-methylsulfonyl-phenyl) -4-carbomethoxy-4-methyl-S-dihydro-1H-pyrazole-1-carboxamide

N- (4-chlorophenyl) -3- (4-methylthiophenyl) -4-carbomethoxy-4-methyl ^^ -dihydro-1H-pyrazole-1-carboxamide ν

N- (4-chlorophenyl) -3- (4-trifluoromethylphenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-chlorophenyl) -3-phenyl-4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-Chlοrphenyl) -3-phenyl-4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-chlorophenyl) -3-phenyl-4-dimethylcarboxamido-4-methyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N- (4-chlorophenyl) -3-phenyl-N _f 4-bis-carboroneethoxy-4-methyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N- (4-Di-fluoro-thoxyphenyl) -3- (3-chloro-4-trifluoroolylthylphenyl) -4-carboethoxy-4-methyl-4 _# 5-dihydro-1H-pyrazole: ol-1-carboxamide

N- (4-difluoromethoxyphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5 ~ dihydro-iH-pyrazol-l ~ carboxamide

N- (4-Dxraethylaminoxyphenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-raethyl-4,5-dihydro-pyrazol-l-.lh-carboxamide

N- (4-dinethylsulfonamidophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-ethyl-4,15-dihydro-1H-pyrazole- ₁

J) carboxamide

N- (4-Dimethylsulfonamidophenyl5-3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4 _f 5-dihydro-lH-pyrazol-l-carboxamide

N- (4-fluorophenyl) -3- (4-chlorophenyl) -4-carbo1iiethoxy-4-raethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-fluorophenyl) -3- (4-broraphenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-fluorophenyl) -3- (4-fluorophenyl) -4-carbomethoxy-4-methyl "4,5-dihydro-1H-pyrazole-1-carboxaraid "

N- (4-fluorophenyl) -3-phenyl-4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-0odphenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Hethoxyphenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxaniid

N- (4-methylphenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide ¹

N- (4_Methylsulfonylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH ~ pyrazol-l-carboxaniid

M_ (4-methylsulfonylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (4-methylsulfonylphenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxatnid

M- (4-Hethylsulfonylphenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxaraid

N- (4-methylthiophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-4, o-dihydro-lH-pyrazol-l-carboxamide

N- (4-methylthiophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-raethyl ^ .S-dihydro-lH-pyrazol-l-carboxatnid

N- (4-methylthiophenyl) -3- (4-chlorophenyl) -4-carboraethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxatnid

N- (4-Nitrophenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-raethyl-4 _L S -dihydro-1H-pyrazole-1-carboxaraid

N- (4-nitrophenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-nitrophenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4,5-dihydro-lH-pyrazol-1-carboxainid

N- (4-trifluoromethoxyphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-cahenoethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-caΓ-carboxamide

N- (4-trifluoromethoxyphenyl) -3- (4-chlorophenyl) ~ 4-carboethoxy-4-methyl-4,5 ~ dihydro-lH-pyrazol-l-carboxamide

M- (4-Trimethylammoniumphenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-raethyl-4,5-dihydro-lH-pyrazol-l-carboxamide ^ .odid

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-dimethylcarbamoyl-4-methyl-4 ₁ 5-dihydro-1H-pyrazole-1-carboxanilide

ISI (4-trifluoromethoxyphenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-trifluoromethylpheriyl) -4- (3-methylthiopropyl) -4-acetyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluorothylphenyl) -3- (3-chloro-4-trifluorinated phenyl) -4- (3-methylthiopropyl) -4-carbomethoxy-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4- (2-chloroallyl) -4 _J 5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4- (2-methylthioethyl) -4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4- (3-cyanopropyl) -4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4- (4-chlorophenyl) -4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro) - trifluorinated phenyl) 4-carboethoxy-4- (4-difluoromethoxyphenyl) -4,5-dihydro-IH-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4- (4-trifluoromethoxyphenyl) -4,5-dihydro-1H-

pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro ^ trifluoromethylphenyl) -4-carboethoxy-4- (4-trifluoromethylphenyl) -4,5-dihydro-LH

pyrazole-1-carboxamide

M- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluorraethylphenyl) -4-carboethoxy-4-acetyl-4,5 ~ dihydro-lH-pyrazol-l-carboxainid

M- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-allyl-4,5-dihydro-lH-pyrazol-1-carboxaraid

\

· '.'

M- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-benzyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-carbornethoxy-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-ethyl-4,5-dihydro-lH-pynazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methallyl-4,5-dihydro-lH-pyrazol-1-carboxatnid

N- (4-trifluoromethylphenyl) -3- (3-chloro-1-trifluoromethyl-phenyl) -4-carboethoxy-4-methoxymethyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-tri fluorine thylphenyl) -3- (3-chloro ^ -trifluorme thylphenyl) 4-carboethoxy-4-methyl-4 _f S-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-trifluorothylphenyl) -4-carboethoxy-4-methyl-N- (2-methoxyethylsulfenyl) -4,5-dihydrolH-pyrazole-1-carboxamide

N- (4-TrifluormethylphenylJ-S- (S-Chiot ^ trifluoromethylphenyl) -4-carboethoxy-4-methyl-N- (2-nitrophenylsulfenyl) -4,5-dihydro-

lH-pyrazol-1-carboxamide

<J N- (4-trifluoromethylphenyl) -3- (3-chloro-trifluoromethylphenyl) -4-carboethoxy-4-methyl-N-acetyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-caOHethoxy-4-methyl-N-caΓboethoxy-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluorophenyl) -3- (3-chloro-3-trifluoromethylphenyl) -4-caethoxy-4-methyl-N-caΓbhomethoxy-4 _# 5-dihydro-1H-pyrazole

1-carboxamide

f -: \ N- (4-trifluorothylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-N-carbomethoxycarbonyl-4,5-dihydro-1H-pyrazole-1 -carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-N-carbomethoxysulfenyl-4,5-dihydro-1H-

pyrazol-1-carboxaraid

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl-1-10-dimethylcarbamoyl-4,5-dihydro-1H-

pyrazole-1-carboxamide

M- (4-trifluoromethylphenyl) -3- (3-chloro-tert-trifluorophenyl) -4-carboethoxy-4-methyl-N-formyl-4,5-dihydro-1H-pyrazole-1

carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluorinated phenyl)

4-carboethoxy-4-methyl ^ ί-methoxymethyl-4,5-dihydro-lH-pyrazol-1-carboxaraid

N- (4-trifluoromethylphenyl) -3- (3-chloro-1-trifluoromethylphenyl) -4-carboethoxy-4-methyl-N-methyl-4,5-dihydro-1H-pyrazole-1

carboxamide

M- (4-Trifiuormethylphenyl) -3- (3-chloro-4-trifluorinethylphenyl) ·

4-carboethoxy-4-methyl-N-fflethyl3ulfeπyl-4,5-dihydro-lH-pyrazole-1-carboxamide

M- (4-trifluoromethylphenyl) -3- (3-chloro-4 * trifluorinethylphenyl) -

4-carboethoxy-4-methyl-N-trifluoroacetyl-4,5-dihydro-lH-pyrazole-1-carboxamide

M- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methylthiomethyl-4,5-dihydro-1H-pyrazole-1

carboxamide

M- (4-trifluoromethylphenyl) -3- (3-chloro-trifluorothylphenyl) -4-carboethoxy-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethyl-phenyl) -3- (3-chloro-4-trifluoro-ethyl-phenyl) -4-methyl-4-acetyl-4,5-dihydro-1H-pyrazole-1-carboxanilide

M- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-methyl-4-carbomethoxy-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-acetyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Trifluorinethylphenyl) -3- (3-chloro-4-trifluoromethylphenyl) -4-phenyl-4-carbomethoxy-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4_Trifluormethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropylJ ^ -acetyl ^ jS-dihydro-lH-pyrazol-l-carboxamide

N- (4-Trxfluormethylphenyl) -3- (4-chlorophenyl) -4- (3-methylthiopropyl) -4-carbomethoxy-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (2-chloroallyl) -4 _# 5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (2-methylthioethyl) -4 _L 5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (S-cyanopropylJ ^^ S-dihydro-lH-pyrazol-l-carboxatnid

N- (4-trifluoro-ethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (4-chloro-phenyl) -4 _# 5-dihydro-1H-pyra-2-ol-1-carboxaraid

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (4-difluoromethoxyphenyl) -4 _# 5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoroethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (4-trifluoro-araoxyphenyl) -4- _f, 5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- (4-trifluoromethylphenyl) -4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-acetyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Trifluorraethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-allyl ^ jS-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-ben2yl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-carboethoxy ^ / S-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-ethyl ^ iS-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoroethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-raethallyl-4,5-dihydro-1H-pyrazole-1-carboxamide) '

N- (4-Trifluorenethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methoxymethyl-4, S-dihydro-lH-pyrazol-l-carboxamide

N- (4-Trifluorinethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-Trifluorraethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-iZ-methoxyethylsulfenylJ ^ iS-dihydro-lH-pyrazol-l-

carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N- (2-nitrophenylsulfenyl) -4,5-dihydro-lH-pyrazol-l- carboxamide

N- (4-Trifluoroethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-acetyl-4 _# 5-dihydro-1H-pyra-2-ol-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-carboethoxy ^ .S-dihydro-lH-pyrazol-l-carboxamide

N- (4-Trifluormethy! Phenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-carboraethoxy-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-carbornethoxycarbonyl-4,5-dihydro-lH ~ pyrazol-lcarboxamid

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-carbomethoxysulfonyl-4 _# 5-dihydro-1H-pyrazole-1

carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-dimethylcarbamoyl ^ 4,5-dihydro-lH-pyra2ol-l-carboxamide

W N - (4-trifluoroethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-ethyl-N-formyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Trifluorinethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-methoxymethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-N-methylsulphenyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4- ^ <: J methyl-N-trifluoroacetyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methylthiomethyl-4, B ^ ihydro-lH-pyrazol-l-carboxamide

N- (4-Trifluorinethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-phenyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chiοrphenyl) -4-carbornethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-methyl-4-acetyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-methyl-4-carbomethoxy ^ .S-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4-acetyl ^^ S-dihydro-lH-pyrazol-i-carboxamide

N- (4-trifluoro-ethyl-phenyl) -3- (4-chlorophenyl) -p-phenyl-1-carbomethoxy-1-S-dihydro-1H-pyrazole-1-carboxamide

N- (4-Trifiuorraethylphenyl) -3-phenyl-4-carboethoxy-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3-phenyl-4-carbomethoxy-4-tnethyl-4,5-dihydro-lH-pyrazol-l-carboxamide

N- (4-trifluoromethylphenyl) -3-phenyl-4-dimethylcarbamoyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N-phenyl-3- (3-chloro-4-trifluoromethylphenyl) -4-carboethoxy-4-methyl ^ .S-dihydro-lH-pyrazol-l-carboxamide

N-phenyl-3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydrolH-pyrazole-1-carboxamide

N-phenyl-3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazol-1-carboxaraid

The invention includes unique methods for preparing 1-substituted-4-substituted-4,5-dihydro-1H-pyrazoles. One such method involves dissolving a 1-substituted-4 ₁ 5-dihydro-1H-pyrazole in an aprotic solvent, mixing a strong base with the resulting solution,

Deprotonation at the 4-position of the pyrazole ring and subsequent addition of an alkylating or acylating agent, wherein the l-substituted-4,5-dihydro-1H-pyrazole dissolved in the aprotic solvent is a 1-substituted-4-monosubstituted-4,5- Dihydro-lH-pyrazole must be when the required end product is an l-substituted-4,4-disubstituted-4,5-dihydro-lH-pyrazole. Methods for preparing 1-substituted-4-mono-substituted-4,5-dihydrol-H-pyrazole and 1-substituted-1-substituted-1-S-dihydro-1H-pyrazole are known to those skilled in the art (See, for example, U.S. Patent No. 4,156,007 ) and are described in Examples A to CJ.

In aer embodiment of the method which can be dissolved in the aprotic solvent l-substituted-4,5-dihydro-lH-pyrazol added to the base or the base may be the dissolved in the aprotic solvent l-substituted-4,5-dihydro -lH-pyrazole are added. Oede's 1-substituted-4,5-dihydro-1H-pyrazole can be dissolved in the aprotic solvent. Examples of 1-substituted-.S-dihydro-1H-pyrazoles which can be used in the process of the invention include, but are not limited to:

N, 3,4-tris (4-chlorophenyl) -4,5-dihydro-lH-pyrazol-lcarboxamid

N, 3-bis (3,4-dichlorophenyl) -4-phenyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-chrorphenyl) -4-phenyl-4,5-dihydro-lH-pyrazol-lcarboxamid

N, 3-bis (4-chlorophenyl) -4- (2-methylethyl) -4,5-dihydro-IH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4- (2-methylpropyl) -4,5-dihydro-IH-pyrazol-1-carboxaraid

N, 3-bis (4-chlorophenyl) -4- (4-chlorobutyl) -4,5-dihydro-IH-pyrazole-1-carboxamide

N, 3-bis (4-chlorophenyl) -4-cyclohexyl-4,5-dihydro-lH-pyrazol-1-carboxaraid

N t 3-bis (4-chlorophenyl) -4-ethyl-4,5-dihydro-IH-pyrazol-lcarboxamid

N, 3-3is- (4-chlorophenyl) -4-phenyl-4,5-dihydro-IH-pyrazol-lthiocarboxamid

N, (3-chlorophenyl) -3- (4-chlorophenyl) -4-phenyl-4,5-dihydro-lH-pyrazol-1-carboxaniid

N_ (4-bromophenyl) -3- (4-fluorophenyl) -4-methyl-4,5-dihydro-lH-pyrazol-1-carboxaraid

N-4-Carboethoxyphenyl) -3- (4-chlorophenyl) -4-phenyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N- (4-Carboisopropoxyphenyl) -3- (4-chlorophenyl) -4-phenyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (2,4-dichlorophenyl) -3- (4-chlorophenyl) -4-phenyl-4,5-dihydro-IH-pyrazol-l-carboxaraid

N- (2-pyridyl) -3- (4-chlorophenyl) -4-phenyl-4,5-dihydro-lH-pyrazol-1-carbpxamid

- Ill -

N- (3,4-dichlorophenyl) -3,4-bis- (4-chlorophenyl) -4,5-dihydro-IH-pyrazole-l-carboxamide

N- (3 _# 4-dichlorophenyl) -3- (4-difluoromethoxyphenyl) -4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (3,5-dichlorophenyl) -3- (4-chlorophenyl) -4-phenyl-4,5-dihydrolH-pyrazole-1-carboxamide

N- (3-chlorophenyl) -3- (4-chlorophenyl) -4-phenyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (3-cyanophenyl) -3- (4-chlorophenyl) -4-phenyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (3-phenoxyphenyl) -3- (4-chlorophenyl) -4-phen.yl-4,5-dihydro-IH-pyrazole-l-carboxamide

N- (3-pyridyl) -3- (4-chlorophenyl) -4-phenyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N- (3-Trifluorinethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-phenyl-4,5-dihydro-lH-pyrazol-1-carboxaraid

N "3-Bis- (4-trifluorinethylphenyl) -4-phenyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N, 3-bis (4-trifluoromethylphenyl) -4-methyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-methyl-4,5-dihydro-IH-pyrazol-1-carboxaraid

N- (4-bromophenyl) -3- (4-chlorophenyl) -4-phenyl-4,5-dihydro-lH-pyrazol-1-carboxaraid

N- (4-carboethoxyphenyl) -3,4-diphenyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-Carboethoxyphenyl) -3- (4-chlorophenyl) -4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamide

N- (4-Carboisopropoxyphenyl) -3,4-diphenyl-4,5-dihydro-lH-pyrazol-l-carboxamld

N- (4-Carboisoproppxyphenyl) -3- (4-chlorophenyl) -4-phenyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-Carbomethoxyphenyl) -3- (4-chlorophenyl) -4-phenyl-4,5-dihydro-lH-pyrazol-1-carboxatnid

M- (4-chlorophenyl) -3,4-diphenyl-4,5-dihydro-lH-pyrazol-lcarboxamid

N- (4-chlorophenyl) -3- (3,4-dichlorophenyl) -4-phenyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N- (4-chlorophenyl) -3- (4-bromophenyl) -4-methyl-4,5-dihydro-IH-pyrazol-1-carboxamxd

N- (4-chlorophenyl) -3- (4-difluoromethoxyphenyl) -4-phenyl-4,5-dihydro-lH-pyrazol-1-carboxaraid

N- (4-chlorophenyl) -3- (4-fluorophenyl) -4-methyl-4,5-dihydro-IH-pyrazole-1-carboxamide

in ~ τ ·

M (4-chlorophenyl) -3-phenyl-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-Difluorinethoxyphenyl) -3- (4-chlorophenyl) -4-phenyl-4,5-dihydro-lH-pyrazol-l-carboxaniid

N- (4-fluorophenyl) -3- (4-chlorophenyl) -4-phenyl-4,5-dihydro-IH-pyrazole-1-carboxamide

N- (4-nitrophenyl) -3- (4-chlorophenyl) -4-phenyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N. (4-phenoxyphenyl) -3- (4-chlorophenyl) -4-phenyl-4,5-dihydro-IH-pyrazole-l-carboxamide

N- (4-phenyl) -3- (4-chlorophenyl) -4-phenyl-4,5-dihydro-lH-pyrazole-1-carboxamide

N- (4-pyridyl) -3- (4-chlorophenyl) -4-phenyl-4,5-dihydro-IH-pyrazole-1-carboxamide

The base used is preferably a strong base, i. h, a base whose strength is sufficient to deprotonate the 4,5-dihydro-1H-pyrazole at the 4-position of the pyrazole ring. Therefore, a base is required whose corresponding acid has a pKa of at least about 10.

Suitable bases for use in the process include, but are not limited to, alkali metal hydroxides, alkaline earth hydroxides, alkali metal alkoxides, alkaline earth alkoxides, alkali metal hydrides, alkaline earth hydrides, alkali metal oxides, alkaline earth oxides, alkali metal amides, alkaline earth amides, alkyllithium, aryllithium or other strong bases known to those skilled in the art. The preferred bases are alkali metal amides. The most preferred base is lithium diisopropylamide.

The reaction must be carried out in the presence of an aprotic solvent. Suitable aprotic solvents are those which are not significantly deprotonated under reaction conditions. Aprotic solvents useful in carrying out the process of the present invention include, but are not limited to, dialkyl ethers, tetrahydrofuran, aliphatic hydrocarbons, aromatic hydrocarbons, aliphatic alcohols, amines, ammonia, dialkylamides, dialkyl sulfoxides, dialkyl sulfones, polyalkyl phosphoric acids, and other solvents known to those skilled in the art , Preferred solvents are dialkyl ethers, ammonia, tetrahydrofuran and amines. The most preferred solvent is tetrahydrofuran.

The alkylating and / or acylating agents useful for carrying out the process of the invention vary with the particular compound synthesized. For example, to effect methylation, suitable alkylating agents would include, but are not limited to, methyl chloride, methyl bromide, methyl iodide, methylaryl sulfenates, methyl alkyl sulfonates, methyl sulfate, trimethyloxonium salts, methyl halo sulfonates, and other methylating agents known to those skilled in the art. Preferred methylating agents are methyl chloride, methyl bromide, methyl iodide and methyl sulfate. The most preferred methylating agent is methyl iodide. Examples of acylating agents include, but are not limited to: alkanoyl chlorides, aroyl chlorides, alkyl chloroformates, aryl chloroformates, alkyl carbonates, aryl carbonates, alkyl isocyanates, aryl isocyanates, alkyl isothiocyanates, aryl isothiocyanates, dialkylcarbamoyl chlorides, alkyl chlorothioformates, aryl chlorothioformates, dialkyl carbodiimides, alkylaryl carbodiimides, diaryl carbodiimides, carbon dioxide and carbon disulfide. Those skilled in the art will be able to choose other suitable alkylating agents and / or acylating agents to introduce other Y groups.

The reaction temperature can be varied within a considerable range. In general, the reaction is carried out at a temperature of about - 120 ⁰ C to about 200 ⁰ C, preferably at a temperature of about -78 ⁰ C to about 100 ⁰ C. The reaction can be carried out under normal pressure. The most favorable temperature is -10 ⁰ C. The yield can be improved by conducting the reaction at temperatures from -80 ⁰ C to -30 ⁰ C using is performed by acylating agents.

To carry out the process, the substances are preferably used in stoichiometric amounts. An excess of one or the other component brings no significant benefits. After completion of the reaction, acetic acid is added to neutralize the reaction.

A second process for obtaining compounds of the invention wherein Y is a group of formula

C-G (group B) involves treating a beta-dicarbonyl compound of formula II

if if

AC-CH ₀ -CG II

wherein A, X and G have the meanings described above for formula I, with a mixture of hydrazine and formaldehyde hyd to produce a 3-aryl-4-monosubstituted-4,5-dihydropyrazoles of the formula

f ·

Il

CH ₂

Il

wherein A, X and G have the meanings explained above for formula I. The treatment of the dihydropyrazole of formula III with an aryl isocyanate gives the N-aryl-3-aryl-4-monosubstituted-4,5-dihydropyrazole-1-carboxamides according to the invention.

Further treatment of this 1-substituted-4-mono-substituted-4,5-dihydropyrazole-1-carboxamide with a base and then with an alkylating agent or acylating agent gives the N-aryl-3-aryl-4,4-disubstituted-4,5 invention -dihydropyrazole-1-carboxamides ·

In carrying out the process for obtaining a 3-aryl-4-mono-substituted-4,5-dihydropyrazole of formula III, any beta-dicarbonyl compound of formula II can be used. Examples of beta-dicarbonyl compounds that can be used in the process of the invention include, but are not limited to:

2-endo-norbornyl-3- (3-chloro-4-difluormethylphenyl) -3-oxopropanoate;

2-endo-norbornyl-3- (4-chlorophenyl) -3-oxo-propanoate;

2-Methylthiöethyl ~ 3- (3-methyl-4-trifluoromethylphenyl) -3-oxopropanoate;

2-Methylthioethy1-3- (4-chlorophenyl) -3-oxo-propanoate;

3'-trifluoromethylbenzyl 3- (3-chloro-4-difluoromethoxyphenyl) -3-oxo-propanoate;

3'-trifluoromethylbenzyl-3- (4-chlorophenyl) -3-oxo-propanoate; 3- (3-methyl-4-trifluoromethylphenyl) -3-oxo-propanamide;

N, N-Diethyl-3- (3-fluoro-4-trifluoromethylphenyl) -3-oxo-propanamide;

N, N-dimethyl-3- (3-chloro-3-trifluorophenyl) -3-oxo-propanamide;

N-Cyclopentyl-3- (4-chloro-3-trifluoromethylphenyl) -3-oxo-propanamide;

N-ethyl-N-methyl-S-CS-chloro ^ difluormethylphenyl) -3-oxo-propanamide; ...

N-methyl-N-phenyl-3- (3-chloro-4-trifluorrnethoxyphenyl) -3-oxo-propanamide; N-phenyl-3- (2-chloro-4-trifluoromethylphenyl) -3-oxo-propanamide; N-Propyl-3- (3-bromo-4-trifluoromethylphenyl) -3-oxo-propanamide; Allyl-3- (3-chloro-4-trifluoromethylphenyl) -3-oxo-propanoate; Allyl-3- (4-chlorophenyl) -3-oxo-propanoate; Cyclopentyl-3- (4-chlqr-3-trifluoromethylphenyl) -3-oxo-propanoate; Cyclopentyl-3- (4-chlorophenyl) -3-oxo-propanoate; Ethyl-3- (3-fluoro-4-trifluoromethylphenyl) -3-oxo-dithiopropanoat; Ethyl-3- (3-f1uor-4-phenyl trifluormethy!) -3-oxo-propanoate; Ethyl-3- (4-chlorophenyl) -3-oxo-propanoate;

Methyl-3- (3-chloro-4-trifluoromethylphenyl) -3-oxo-dithiopropanoat;

- 113 -

Methyl 3- (3-chloro-4-trifluoroethylphenyl) -3-oxo-propanoate; Methyl-3- (4-chlorophenyl) -3-oxo-propanoate; Phenyl-3- (2-chloro-4-trifluoromethylphenyl) -3-oxo-dithiopropanoat;

Phenyl-3- (2-chloro-4-trifluoromethylphenyl) -3-oxo-propanoate; Phenyl-3- (4-chlorophenyl) -3-oxo-propanoate; Propyl-3- (3-bromo-4-trifluoromethylphenyl) -3-oxo-dithiopro-

nannfi 1 * ♦

panoat;

Propyl-3 ~ (3-bromo-4-trifluoromethylphenyl) -3-oxo-propanoate; Propyl-3- (4-chlorophenyl) -3-oxo-propanoate;

t-Butyl-3- (3-chloro-4-trifluoromethoxyphenyl) -3-oxo-propanoate; or

t-Butyl-3- (4-chlorophenyl) -3-propanoate.

Preferably, a substantially equimolar mixture of hydrazine and formaldehyde is used.

The reaction may be carried out in the presence or absence of a solvent. Suitable solvents are those which impart some solubility to the constituents of the reaction mixture. Suitable solvents useful in the practice of the process include, but are not limited to: water, dialkyl ethers, tetrahydrofuran, aliphatic hydrocarbons, aromatic hydrocarbons, aliphatic alcohols, tertiary amines, dialkyl

amides, dialkyl sulfoxides, dialkyl sulfones, polyalkyl phosphoramides, and other solvents known to those skilled in the art. Preferred solvents are aliphatic alcohols, tetrahydrofuran and tertiary amines. The most preferred solvent is methanol »

Due to the basic nature of hydrazine, the reaction can be carried out in the presence or absence of an additional base. Suitable additional bases for use in this method include, but are not limited to:

rS, "alkali metal hydroxide, alkaline earth hydroxide, alkali metal alkoxide, X}

Alkaline earth oxide, alkali metal oxide, alkaline earth oxide, tertiary. Amines, amidines, guanidines and other professionals known bases · _s

The reaction temperature can be varied within a considerable range. In general, the reaction is carried out at a temperature of about - 120 ⁰ C to about 200 ⁰ C, preferably at a temperature of about - 78 ⁰ C to about 100 ⁰ C. The reaction can take place under normal pressure · The most favorable temperature is about 20 ⁰ C.

Treatment of the dihydropyrazole of formula III with an Oj aryl isocyanate gives the M-aryl-3-aryl-4-monosubstituted-4,5-dihydropyrazole-1-carboxamides according to the invention.

In carrying out the process for the preparation of an inventive 3-aryl-4-mono-substituted-4,5-dihydropyrazol-1-carboxamide may be any aryl isocyanate of the formula IV

B-N = C = O IV

wherein B has the meaning explained in formula I, can be used. Examples of aryl isocyanates that can be used in the process of the invention include, but are not limited to:

3,4-dichlorophenyl; S-bromo ^ -diroethylaminophenylisocyanat; S-bromo - ^ - raethylphenyl isocyanate; 3-bromo-4-methylphenylisothiocyanat; S-bromo ^ -trifluormethylphenylisocyanat; 3-bromodifluoromethoxyphenyl isocyanate ; 3-Broradifluorthioraethoxyphenylisocyanat; 3-bromophenyl; 3-Carboethoxyphenylisocyanat; 3-Carboisopropoxyphenylisocyanat; 3-Carbomethoxyphenylisocyanat; S ^ Ghlor- bromdifluormethoxyphenylisocyanat; S-chloro ^ bromdifluorthiomethoxyphenylisocyanat; 3-chloro-4-bromophenyl; S-chloro ^ -carboethoxyphenylisocyanat; S-chloro ^ -carboisopropoxyphenylisocyanat; S-chloro ^ -carbomethoxyphenylisocyanat; 3-chloro-4-cyanophenyl isocyanate;

3-chloro-4-difluormethoxyphenylisocyanat; 3-chloro ~ 4-dimethylaminophenyl isocyanate; 3-chloro-4-fluorphenylisGcyanat; 3-chloro-4- £ ι odphenylisocyanat S-chloro - ^ - tnethylphenylisocyanat;

~ S-chloro-methylsulfinylphenyl isocyanate;

  y '-

S-chloro-methylsulfonylphenyl isocyanate ; S-chloro ^ -methylthiophenylisocyanat; S-chloro ^ -nitrophenylisocyanat; 3-Chiot ^ -trxfluormethoxyphenylisocyanat; S-chloro ^ -trifluorraethylphenylisocyanat; 3-chlorophenyl isocyanate; S-Cyano ^ -carbomethoxyphenylisocyanat; S-cyano - ^ - carbomethoxyphenylisothiocyanat; 3-cyanophenyl;

3-difluoromethoxy-4-methylthiophenylisocyanat; 3-Difluormethoxyphenylisocyanat; 3-Dimethylatninophenylisocyanat;

3-fluoro-4 ~ bromphenyixsocyanat; S-fluoro - ^ - carboethoxyphenylisocyanat; S-fluoro - ^ - carboethoxyphenylxsothiocyanat; S-fluoro - ^ - cyanophenyl; S-fluoro - ^ - Cyanophenylisothiocyanate; 3-fluorophenyl; 3-Dod-4 ~ difluormethoxyphenylisocyanat; 3-0od-4-fluorophenyl isocyanate; 3-Dodphenylispcyanat; 3-methyl-4-trifluorraethoxyphenylisocyanat; 3-methylphenyl; 3-Methylsulfinylphenylisocyanat; 3-Methylsulfonylphenylisocyanat; 3-methylthio-4-raethylsulfinylphenylisocyanat; 3-methylthiophenyl isocyanate S-methythio ^ -bro-ridexfluoromethoxyphenyl isocyanate; S-nitro ^ -bromdifluorthiomethoxyphenylisocyanat; S-nitro ^ -bromdifluorthioraethoxyphenylisothiocyanat;

3-nitrophenyl;

S ^ Trifluorinethoxy -methylsulfonylphenylisocyanat; S-trifluoromethoxy ^ -nitrophenylisocyanat; - '

3-trifluoromethoxy-4-nitrophenyl isothiocyanate; 3-Trlfluormethoxyphenylisocyanat; S-trifluoromethyl ^ -carboisopropoxyphenylisocyanat; S-trifluoromethyl ^ -carboisothiopropoxyphenylisothiocyanat; 3-Trifluorraethyl-4 - ^ odphenylisocyanat;. 3-Trifluorniethylphenylisocyanat; ^ -Brotndifluormethoxyphenylisocyanat; 4-Bromdifluorthioraethoxyphenylisocyanat; 4 "Broraphenylisocyanat; 4-bromophenyl isothiocyanate; 4-Carboethoxyphenyl isocyanate \ 4-Carboisopropoxyphenyl isocyanate; 4-Carbomethoxyphenylisocyanat; 4-chlorophenyl; 4-Chlorphenylisothxocyanat;

4-cyanophenyl; 4-Difluormethoxyphenylisocyanat; 4-Difluormethoxyphenylisothiocyanat; 4-Dimethylarainophenylisocyanat; 4-fluorophenyl isocyanate; 4-0odphenylisocyanat; 4-methylphenyl; 4-methylsulfinylphenyl isocyanate ϊ 4-methylsulfonylphenyl isocyanate ; 4-methylthiophenyl isocyanate, 4-nitrophenyl isocyanate; 4-Pentafluorsulfuranylphenylisocyanat; 4-trifluoromethoxyphenyl isocyanate; 4-Trifluormethoxyphenylisothiocyanat; 4-trifluoromethylphenyl; 4-trifluoromethylphenyl; or phenylisocyanate ·

The reaction may be carried out in the presence or absence of a solvent. "Suitable solvents are those which impart some solubility to the constituents of the reaction mixture and do not react to any appreciable extent with the aryl isocyanate." Suitable solvents useful in the practice of the invention but not limited to: dialkyl ethers, chlorinated hydrocarbons, tetrahydrofuran, aliphatic hydrocarbons, aromatic hydrocarbons, aliphatic alcohols, tertiary amines, dialkylamides, ν>, dialkyl sulfoxides, dialkyl sulfones, polyalkyl phosphoramides, and solvents known to those skilled in the art. Preferred solvents are chlorinated hydrocarbons, tetrahydrofuran and tertiary amines. The most preferred solvent is methylene chloride.

The reaction temperature can be varied within a considerable range. In general, the reaction is carried out at a temperature of about - 120 ⁰ C to about 200 ⁰ C, preferably at a temperature of about -78 ⁰ C to about 100 ⁰ C. The reaction can take place under normal pressure. The cheapest temperature is 45 ⁰ C.

The further treatment of this 1-substituted-4-monosubstituted ^ iS-dihydropyrazol-1-carboxaraid with a base and then with an alkylating agent or acylating agent gives the N-aryl-3-aryl-4,4-disubstituted-4 according to the invention, 5-dihydropyrazol-l-carboxamides.

The methods for carrying out this reaction have been described above and are further illustrated below in Example 77, Method C.

After the preparation of compounds included by formula I according to one of the preceding methods, the

salts according to the invention be prepared by a suitable method recognized in the art «, for example by reacting a metal hydroxide, a metal hydride or an aroin or ammonium salt such. B, a halide, hydroxide or alkoxide with the free acid, or reacting a quaternary ammonium salt such as chloride of a bromide, nitrate, etc. with a metal salt of the invention in a suitable solvent. When metal hydroxides are used as reagents, suitable solvents include water, glyme, dioxane, tetrahydrofuran, methanol, ethanol, isopropanol, etc. When metal hydrides are used as reagents, suitable solvents include nonhydroxylic solvents such as dioxane, glyme * tetrahydrofuran, diethyl ether, hydrocarbons such as toluene, Xylene, hexane, pentane, heptane and octane, dimethylformamide, etc. When amines are used as reagents, suitable solvents include alcohols such as methanol or ethanol, hydrocarbons such as toluene, xylene, hexane, etc., tetrahydrofuran, glyme, dioxane or water Reagents employed include suitable solvents such as water, alcohols such as methanol or ethanol, glyme, tetrahydrofuran, etc. When the ammonium salt is not a hydroxide or alkoxide, an additional base such as potassium or sodium hydroxide, hydride or alkoxide is generally used. The particular choice of solvent depends on the relative solubility of the starting materials and the resulting salts, and slurries can be better used to recover the salts than solutions of certain reagents. In general, equivalent amounts of the starting reagents are used, and the salt formation reaction is carried out at about 0 ^° C to about 100 ^° C, preferably at about room temperature.

The acid addition salts of the present invention may be prepared by any suitable art-recognized method, such as reacting hydrochloric, hydrobromic, sulfuric, nitric,

Phosphoric, acetic, propionic, benzoic acid or other suitable acid with a compound of the invention having basic functionality in a suitable solvent. Suitable solvents include water, alcohols, ethers, esters, ketones, haloalkanes, etc. The particular choice of solvent depends on the relative solubility of the starting materials and the resulting salts, and slurries can be better used to obtain the salts than solutions of certain reagents generally, equivalent molar amounts of the initial _r - used _passage% substances, and the salt formation reaction is conducted at a temperature of about -100 J ⁰ C to about 100 ⁰ C, preferably at about room temperature executed.

Ausföhrunqsbeispiele:

The invention is illustrated by, but is not limited to, the following examples. Table I lists typical 1-substituted-4-substituted-4,5-dihydro-1H-pyrazoles of this invention.

The structures were confirmed by NMR and in some cases by IR and / or elemental analysis. According to Table I ζ- ~ \, described in Examples A to D, the preparation of representative precursors and intermediates. Following Examples A to 0, specific illustrative preparation methods of compounds of Examples 2, 5, 34, 51, 61, 74 (see Method C, Example 77), 77, 92, 95, 98, 115, 130, 138, 145, 147, 150 and 160. Those skilled in the art will recognize that except for the compounds where Z is hydrogen, the Y and Z substituents may be interchanged without departing from the spirit or scope of the invention.

Table I

γ-c-CH,

ι *

A-C-N ^

Ν-C-N

"Β

Example No.,

-C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4

-C ^ H.Cl-4 6 4

-CcHXl-4 6 4

-C ₆ H ₄ Cl- ⁴ -C -HX1-4

-C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4

.C ₆ H ₄ Cl-4 .C ₆ H ₄ Cl-4 C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4

.C ^ .H.Cl-4 6

-C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 .C ₆ H ₄ Cl-4

-CO ₂ CH ₂ CH ₂ SCH ₃

^C 6 ^H 5 -CH ₂ CH (CH ₃ )

-CH ₂ CH ₃ CH ₃

-CH ₂ CH ₃

nvHoCH ··

-CH (CH ₃ ) ₂ -CH ₂ CH (CH ₃ ) ₂

^C 6 ^H 5

* ₄ Cl-4 -CH (CH ₃ ) CH ₂ CH ₃

-C ₆ H ₄ Cl-4

^C 6 ^H 5

Z CH ₃ V U Melting point OC CH ₃ H 0 solid fuel CH ₃ H O 151-153 CH ₃ H 0 128-130 -CH ₂ C ₆ H ₅ H 0 134-136 ^C 6 ^H 5 H 0 oil ^C 6 ^H 5 H 0 solid fuel ^C 6 ^H 5 H 0 solid fuel ^C 6 ^H 5 H 0 solid fuel -CH ₂ CgH ₅ H 0 solid fuel C ₆ H ₅ H 0 solid fuel -CH ₂ CH ₂ CH ₂ CH ₂ Cl H 0 foam H 0 solid fuel

Table I (continued)

Example no.

A.

13 -C-.HX1-4

14 -C ₆ H ₄ Cl-4

15 -C ₆ H ₄ Cl-4

16 -C ₆ H ₄ Cl-4

17 -C ₆ H ₄ Cl-4

18 -C ₆ H ₄ Cl-4

19 -C ₆ H ₄ Cl-4

20 -C ₆ H ₄ Cl-4

21 -C ₆ H ₄ Cl-4

22 -C ₆ H ₄ Cl-4

23 -C ₆ H ₄ Cl-4

24 -C ₆ H ₄ Cl-4

25 -C ₆ H ₄ Br-4

26 -C ₆ H ₄ Br-4

27 -C ₆ H ₄ Cl-4

-C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 .C ₆ H ₄ Cl-4

-Cc.H.Cl-4 6

-C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -CHXl-4

O

-C.-H.C1-4 6

-C ₆ H ₄ Cl-4

-CH (CHj) ₂ -CHgCHgCHgCHj -CH (CH ₃₎ CH ₂ CHj -CHgCHgCH ₂ CHgCl

^C 6 ^H 5 ^C 6 ^H 5

^C 6 ^H 5 C ₆ H ₅

^C 6 ^H 5 -CH (CHgCHj) ₂

-CH

λΟΗ · »-CHgCHgCHgCHj -CHgCHgCHgGggj

2 ^C 6 ^H 5 H U. melting point I CH ₃ H 0 solid fuel ro φ ^CH 3 H 0 Foam ι CH ₃ H 0 foam CH ₃ H 0 89-92 CH ₃ H 0 oil -CHgCH-Chg H 0 oil -CHgCOgCHgC ΪΗ ₃ Η 0 161-165 -CHgCN H 0 138-142 -CH ₂ SCH ₃ H 0 156-158 -CHgOCHj H 0 69-71 ^C 6 ^H 5 H 0 88-93 CH ₃ CH ₃ -CH (CH ₃₎ H 0 130-135 CH ₃ H 0 0 oil oil 0 Semisolid

Table I (continued)

example

C ₆ H ₄ Cl ~ 4

C ₆ H ₄ Cl-4

C ₆ H ₄ F - *

C ₆ H ₄ Cl-4 C ₆ H ₄ Cl-4 C ₆ H ₄ Cl-4

C ₁₅ -H "Cl-4 6

C ₆ H ₄ Cl-4 C ₆ H ₄ Cl-4 C ₆ H ₄ Cl-4

-C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4

-C ^ H.Cl-4 o

-C ₆ H ₄ Cl-4

^G 6 ^H 4 ^Br " ⁴ -C ₆ H ₄ F-4

-C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -CH.Cl-4

D

-C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4

-CHpCH »CH ₃

C HpC HpC H ν

-CH (CH ₂ CH ₃ J ₂

-CH ₂ SCH ₃

-CH ₂ OCH ₃

-CH ₂ CH ₂ CH ₂ CH ₃

-CH ₂ CH ₂ CH ₂ CH ₃

-CHpCH

-CH ₂ CH ₂ CH ₂ CH ₂ OCH ₃

-CH ₂ CH ₂ CH ₂ GN

CH ₃

-CH ₂ CH ₂ OCOCH ₃

-CH ₂ OCH ₂ CH ₂ OCH ₃

CH ₃

CH,

CH ₃

-CH ₂ CHaCH ₂

-CH ₂ CH ₂ OCH ₃

-CH ₂ CH ₂ CHeCH ₂

-CH ₂ CH ₂ CH ₂ CH ₂ CHeCH ₂ -CH ₂ CH ₂ SC ₆ H ₅

V U Melting point ° C H 0 oil H 0 solid fuel H 0 oil H 0 foam H 0 oil H 0 oil H 0 solid fuel H 0 solid fuel H 0 oil H 0 oil H 0 solid fuel H 0 oil H 0 60-65 H 0 solid fuel H 0 125-128 H 0 solid fuel

Table I (continued)

Example no. A B Y Z CH ₃ V H U melting point 44 -CgH ₄ Cl-4 -CgH ₄ Cl-4 -COCH ₃ -CH (OH) CH ₃ H 0 solid fuel 45 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 CH ₃ CH ₃ H 0 46 -C ₆ H ₄ Cl-4 -CgH ₄ Cl-4 -CcH.Cl-4 O 4 -C ₆ H ₄ Cl-4 H 0 solid fuel 47 -C ₆ H ₄ Cl-4 -CgH ₄ Cl-4 CH ₃ H 0 solid fuel 48 -CgH ₄ Cl-4 CgHjClg- 2,4 ^C 6 ^H 5 CH ₃ H 0 179-181 49 -CgH ₃ Cl ₂ -S, / I · CgH ₄ Cl-4 ^C 6 ^H 5 ^C 6 ^H 11 H 0 110-114 50 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 CH ₃ CH ₃ CH ₃ 0 162-164 51 -CgH ₄ Cl-4 -C ₆ H ₄ Cl-4 ^C 6 ^H 5 C ₆ H ₅ H 0 132-135 52 -C _c H.Cl-4 O 4 / -C ₆ H ₄ Cl-4 -CH (OH) CH ₃ ^C 6 ^H 5 H 0 foam 53 -CgH ₄ Cl-4 -C ₆ H ₄ Cl-4 -COCH ₃ CH ₃ CH ₃ 0 foam 54 -C ₄ -H. Cl-4 ο 4 -CgH ₄ Cl-4 -CH ₂ CH (CHj) ₂ CH ₃ H 0 oil 55 -C ₆ H ₄ Cl-4 CgH ₃ C ^ -S, 4 C ₆ H ₅ CH ₃ H 0 solid fuel 56 -C ₆ H ₄ Cl-4 -C ₆ H ₃ Cl ₂ -S, 5 ^G 6 ^W 5 CH ₃ H 0 solid fuel 57 -C ₆ H ₄ Cl-4 -C.-H.C1-3 O 4 ^C 6 ^H 5 CH ₃ CH ₃ 0 solid fuel 58 -C-HXl-4D 4 -CgH ₄ Cl-4 -C ₆ H ₄ Cl-4 CH ₃ H 0 solid fuel 59 -CgH ₄ Cl-4 C ₆ H ₃ Cl ₂ -S, 5 -CgH ₄ Cl-4 0 solid fuel

Table I (continued)

Example no. A B Y ^CH 3 Z ^C 6 ^H 5 V H U Melting point on 60 -C ₆ H ₃ Cl ₂ -S ^ i C ₆ HjCl ₂ -3.5 ^C 6 ^H 5 CH ₃ H 0 solid fuel 61 -C ₆ H ₃ Cl-S ^ V -0 ^, 010-3,4 ο 3 2 ^C 6 ^H 5 CH ₃ H 0 solid fuel 62 f ^ U ^^ Tt y V ^ f » Π» \ j <& * *% ^ J t I -CgHjClg-3,5 CH ₃ / ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ CH ₃ 0 solid fuel 63 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl ^ -CHgOH ^C 6 ^H 5 H 0 oil 64 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -CHgOCOCH ₃ ^C 6 ^H 5 H 0 140-147 65 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -CHgCHgCHgCl CH ₃ H 0 146-150 66 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -COgH ^G 6 ^H 5 H 0 solid fuel 67 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -COgH CH ₃ H 0 solid fuel 68 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -COgNa. CH ₃ H 0 solid fuel 69 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -CHgCHgSCH ₃ ^CH 3 H 0 solid fuel 70 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 CH ₃ -CHgCH (OH) CHj H 0 oil 71 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -CH ₂ CH ₂ SCH ₂ CH ₃ CH ₃ H 0 solid fuel 72 -C ₆ H ₄ Cl- ⁴ -C ₆ H ₄ Cl-4 CH ₃ -CHGCHGCHGN ₃ H 0 oil 73 -C ₆ H ₄ Cl-4 -CH ^ Cl-4 ο ** -CO ₂ CH ₃ H H 0 oil 74 -C..H.C1-4 6 4 -C ₆ H ₄ Cl-4 -COgH H H 0 138-150 75 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 0 solid fuel

Table I (continued)

Example no. A B -C ₆ H ₄ Cl-4 Y ^C 6 ^H 5 Z V U Melting point oc - 133 - 76 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -CO ₂ CH ₃ -CHnCO oCH-, H 0 solid fuel 77 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -CO ₂ CH ₃ CH ₃ H 0 125.5 to 126.5 78 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -CH ₂ CO ₂ H ^C 6 ^H 5 H 0 solid fuel 79 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 C ₆ H ₅ ^C 6 ^H 5 H 0 solid fuel 80 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 CH ₃ CH ₃ CN 0 solid fuel 81 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -CH ₂ CH ₃ , -CH ₂ CH ₂ SO ₂ C 0 solid fuel 82 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -CH ₂ CH ₂ SOCH ₃ -CO ₂ CH ₂ CH ₃ ^C 6 ^H 5 -CH ₂ CH ₃ H 0 solid fuel 83 84 85 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 ^C 6 ^H 5 -C ₆ H ₄ Cl-4 -CH ₂ CO ₂ CH ₃ CH ₃ CH ₃ CH ₃ XXX 0 0 0 Solid 175-176 86 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 ^C 6 ^H 5 CH ₃ H 0 oil 87 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 CH ₃ CH ₃ -COCH ₃ 0. foam 88 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -CO ₂ CH ₂ SCH ₃ -SCH ₃ H 0 oil 89 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -COCH ₂ CH ₃ CH ₃ H 0 oil 90 -C ₆ H ₄ Cl-4 -C ₆ H ₄ (CO ₂ CH ₂ CH ₃ ) -4 C ₆ H ₅ CH ₃ H 0 solid fuel 91 -C-.H.C1-4 -C ₆ H ₄ Cl-4 ο -CON (CH,) CH ₃ H 0 81-83 92 -Q ₆ H ₄ Cl-4 CH ₃ H 0 194-197

Tabel l e I (continued)

Example no. A -C ₆ H ₄ Cl-4 93 -C ₆ H ₄ Cl-4 ^ ** t * l ^^ 1 λ ν / ^ "Π λ v ^ J · l * 94 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 95 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 96 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 97 98 6 4 fy tJ f \ "1 / t -C ₆ H ₄ (CO ₂ 99 -C ₆ H ₄ Cl-4 -CaH.CI-4 6 4 .100 -C ₆ H ₄ Cl-4 -Ο, -ΗΧΐ-4 D 4 101 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 102 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 103 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 104 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 105 -C ^ .H.Cl-4 6 4 6 4 106 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 107 ^C 6 ^H 5

CH

-CH 2 ^CH Goh 3 CO 2 ^CH gCH C ₆ H 5 CO 2 ^CH 3 -CS gCH 3 C ₆ H 5 gCHGCH ₃ CO gCH gCH

-COgCHgCHgCH ₃

CN

CH ₃

CH ₃

CH ₃

CH ₃

CH ₃

CH ₃

CH ₃

CH,

-COgCH (CH _{3) 2} g -COgCH chgn (CH ₃₎ g CH ₃ -CO ₂ CHgCHgN (GH ₃₎ HCl CH

-COgCH ₃

-CHgCHBrCHgBr

-COgCH ₃

CH CH.

H H H

U O O O

-CH ₂ OCH ₃ O

CH ₃

-CO _n CH-

O O O O O O O Q

CH

'2 ^W ' 3 HO

H O

melting point

solid fuel

solid fuel

oil

117-120

solid fuel

foam

solid fuel

solid fuel

solid fuel

solid fuel

solid fuel

100-103

solid fuel

oil

Table I (continued)

Example no. A B Y Z CH ₃ V H IJ Melting point ⁰ C 108 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -CO ₂ CH ₂ CH ₂ SO ₂ CH ₃ CH ₃ H O foam 109 -C ₆ H ₄ Cl- * -C ₆ H ₄ Cl-4 -COCgH ₄ Cl-4 -CH ₂ CHClCH ₂ Cl H 0 foam 110 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 CH ₃ CH ₃ H 0 solid fuel 111 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -COCH ₂ CH ₂ CH ₃ CH ₃ H 0 solid fuel 112 -C ₅ H ₄ Cl- * 6. 4 -COC ₆ H ₅ CH ₃ CH ₃ H -COCH ₃ 0 foam 113 114 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -C.-H.Cl-4 D 4 -CON (CH ₂ CH ₃ J ₂ -CO ₂ CH ₃ XXXX 04 04 04 04 -COCH ₃ HH -COCH ₂ CH ₃ 0 0 Solid 147-149 115 116 117 118 -C ₆ H ₄ Cl-4 C ₆ H ₅ C ₆ H ₅ -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -C..H.C1-4 6 4 -C ₄ -H. Cl-4 O 4 -CON (CH ₃ J ₂ -CO ₂ CH ₂ CH ₃ -CON (CH ₃ J ₂ C ₆ H ₅ CH ₃ CH ₃ -COC (CH ₃ J ₃ -CO ₂ CH ₃ OOOO oil 04 oil ^w I solid solid 119 120 -C ₆ H ₄ Cl- * -C ₆ H ₄ Cl-4 -C ₆ H ₄ ClU -C ₆ H ₄ Cl-4 ^C 6 ^H 5 ^C 6 ^H 5 H H 0 0 Solid solid 121 -C - H, Cl-4 o 4 -C ₆ H ₄ Cl-4 -CON (CH ₃ J ₂ CH ₃ -COC ₆ H ₅ 0 solid fuel 122 -C ₆ H ₄ Cl-4 -C ^ H. Cl-4 O 4 ^C 6 ^H 5 CH ₃ -COCF ₃ 0 solid fuel 123 -C-.H.C1-4 ο 4 -C ₆ H ₄ Cl-4 -CO ₂ CH ₃ CH ₃ CHO 0 oil 124 -C ₆ H ₄ Cl-4 _p M Cl -A 0 4 -CO ₂ CH ₃ 0

Table I (continued)

Example no. A B Y 2 V U melting point 125 -C ₆ H ₄ C1 ~ 4 -C ₆ H ₄ Cl-4 -CO ₂ CHj CH ₃ -CH ₂ OCH ₃ 0 solid fuel 126 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -CO ₂ CHj CH ₃ -CO ₂ CH ₂ CHj 0 solid fuel 127 -C ₆ H ₄ C1 ~ 4 -C ₆ H ₄ Cl-4 -CO ₂ CHj CH ₃ -CO ₂ CHeCH ₂ 0 solid fuel 128 -C ₆ H ₄ C1 ~ 4 -C ₆ H ₄ Cl-4 -CO ₂ CHj CH ₃ -CO ₂ C ₆ H ₅ 0 solid fuel 129 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -CSN (CHj) ₂ ^CH 3 H 0 solid fuel 130 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -CO ₂ CH ₃ CH ₃ H S 69-78 131 - ^C 6 ^H 4 ^C1 "" ⁴ -C ₆ H ₄ Cl-4 -CO ₂ CHj CH ₃ -COCHj S 138-141 132 C ₆ H ₅ ~ C ₆ H ₄ F-4 -CO ₂ CHj CHj H 0 115-119 133 ^C 6 ^H 5 -C ₆ H ₄ Br-4 -CO ₂ CHj CH ₃ H 0 130-136 134 -C ₆ H ₄ F-4 -C ₆ H ₄ Cl-4 -CO ₂ CHj CH ₃ H 0 168-173 135 -C ₆ H ₄ F-4 -C ₆ H ₄ Br-4 -CO ₂ CHj CH ₃ H 0 154-158 136 -C ₆ H ₄ F-4 -C ₆ H ₄ F-4 -CO ₂ CHj CH ₃ H 0 143-145 137 -C ₆ H ₄ Ql-4 -C ₆ H ₄ Cl-4 -CO ₀ CH, CH ₃ -CO ₂ CH ₃ 0 100-103 138 139 -C ₆ H ₄ Cl-4 ^C 6 ^H 5 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -CO ₂ CH ₃ -CO ₂ CH ₃ ^CH 3 CH ₃ -CON (CHj) ₂ -CO ₂ CHj 0 0 Solid solid 140 -C H.Br _ß-4 ο 4 -C ₆ H ₄ F-4 -CO ₂ CHj CH ₃ ' H 0 oil 141 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -CO ₂ CHj CH ₃ -COCO ₂ CH ₃ 0 78-87

Table I (continued)

Example no. A B -C ₆ H ₄ F-4 142 -C ₆ H ₄ Cl-4 -CgH ₄ Br-4 143 -CJH _A Cl ~ 4 o ** -C ₆ H ₄ Cl-4 144 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 145 -C - H. C1-4 D 4 -C ₆ H ₄ Cl-4 146 -C ₆ H ₄ Br-4 -C ₆ H ₄ Br-4 147 -C ₆ H ₄ Br-4 -C ₆ H ₄ Cl-4 148 -C ₆ H ₄ CF ₃ -4 -C ₆ H ₄ CF ₃ -4 149 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 150 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 151 -C ₆ H ₄ Cl-4 -C ₆ H ₄ CF ₃ -4 * "* w * f ti * I ^> Γί C wm 152 153 "* 6 4 3" * -C ₆ H ₄ Cl-4 C * U F \ C ^ U ^ 154 -C ₆ H ₄ Cl-4 -C ₆ H ₄ SCH ₃ -4 155 -e ₆ H ₄ ci-4

Y Z V H U melting point -CO ₂ CH ₃ CH ₃ H 0 148-151 -CO ₂ CH ₃ CH ₃ -SCO ₂ CH ₃ 0 105-110 ° 6 ^H 5 ^CH 3 -SCO ₂ CH ₃ 0 foam -CO ₂ CH ₃ CH ₃ H 0 foam -CO ₂ CH ₃ CH ₃ H 0 oil -CO ₂ CH ₃ ^CH 3 H O 114-117 -CO ₂ CH ₃ CH ₃ H 0 145-149 -CO ₂ CH ₃ CH ₃ -SCH ₂ CH ₂ CH ₃ 0 143-146 -CO ₂ CH ₃ -CO ₂ CH ₃ CH ₃ CH ₃ H 0 0 mm mm »oil -CO ₂ CH ₃ CH ₃ H 0 165-167 -CO ₂ CH ₃ CH ₃ H 0 58-60 -CO ₂ CH ₃ CH ₃ H 0 120-122 -CO ₂ CH ₃ CH ₃ 0 114-116

Table I (continued)

Example no. A B Y Z V H U Melting point ⁰ C ι 156 -C ₆ H ₄ Cl-4 -C ₆ H ₄ S0 ₂ CHj-4 -CO ₂ CH ₃ CH ₃ H 0 179-182 Oi oil ω 157 -C ₆ H ₄ Cl-4 -C ₆ H ₄ CHj-4 -CO ₂ CH ₃ CH ₃ -SC ₆ H ₅ 0 122-125 120-123 158 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -CO ₂ CH ₃ CH ₃ -SCH ₂ CH ₂ CH ₂ CN 0 solid fuel 145-146 159 -C ₆ H ₄ Cl- ⁴ -C ₆ H ₄ Cl-4 -CO ₂ CH ₃ CH ₃ ψζ -SCH 0 oil 73-75 160 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -CO ₂ CH ₃ CH ₃ CH ₂ CU ₂ CH ₃ 0 211-212 t -SCH ₃ oil 161 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -CO ₂ CH ₃ CH ₃ H 0 solid fuel 162 6 4 -C ₆ H ₄ SOCH ₃ ^ -CO ₂ CH ₃ CH ₃ H 0 163 -C ₆ H ₄ Cl-4 -C ₆ H ₄ I-4 -CO ₂ CH ₃ CH ₃ H 0 164 -C ₆ H ₄ Cl-4 -C ₆ H ₄ N (CH ₃ ) ₂ -4 -CO ₂ CH ₃ CH ₃ H 0 165 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -COCH (CH ₃ J ₂ CHj H 0 166 -C..H.C1-4O4 -C ₆ H ₄ Cl-4 -COC (CH ₃ ) ₃ CHj H 0 167 -C ₆ H ₄ (N (CH ₃ ) Jr) -4 -CO ₂ CH ₃ CHj H 0 168 -C ₆ H ₄ Cl-4 -C ₆ H ₄ (n (CH ₃ ) ₂ O) -4 -CO ₂ CH ₃ ^CH 3 H 0 169 -C ₆ H ₄ Cl-4 - ^C 6 ^H 4 ^Cf V ³ -CO ₂ CH ₃ CH ₃ H 0 170 -C ₆ H ₄ Cl-4 -CJH.C1-3 0 4 -CO ₂ CH ₃ CH ₃ 0

A B Table I (cont 3 Y -CO ₂ CH ₃ Z CH ₃ V U Melting point o _c Example no. -C ₆ H ₄ Cl-4 -C ₆ H ₄ SCH ₃ - 3- ³ -CO ₂ CH ₃ CH ₃ H 0 solid fuel 171 -CβH.Cl-4 O 4 -C ₆ H ₄ SO ₂ CH CH ₃ -CHOHC ₆ H ₄ F-4 H 0 foam 172 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 -CO ₂ CH ₃ CH ₃ H 0 186-187 173 -C ₆ H ₄ CH ₃ -4 -C ₆ H ₄ Cl-4 -CO ₂ CH ₃ CH ₃ H 0 127-128 174 -C ₆ H ₄ OCH ₃ -4 -C ₆ H ₄ Cl-4 -CO ₂ CH ₃ -CH ₂ CH ₃ H 0 148-149 175 -CJ-I ,, Cl -4 D 4 -C ₆ H ₄ Cl-4 -CON (CH ₃ ) ₂ CH ₃ H 0 141-143 176 -C ₆ H ₄ Cl-4 -C ₆ H ₄ CF ₃ -4 -CO ₂ CH ₃ CH ₃ H 0 152-155 177 -C ₆ H ₄ SCH ₃ -4 -Ce.H.Cl-4b 4 -CO ₂ CH ₃ CH ₃ H 0 131-133 ' 178 ^C 6 ^H 5 -C ₆ H ₄ CF ₃ -4 , 4 -CO ₂ CH ₃ CH ₃ H 0 Oil 133-135 ω 179 ^C 6 ^H 5 -C ₆ H ₃ Cl ₂ -S -CO ₂ CH ₃ CH ₃ H 0 127-130 180 -C ₆ H ₄ SO ₂ CH ₃ ^ -C ₆ H ₄ Cl-4 -CO ₂ CH ₃ CH ₃ H 0 205-207 181 -C ₆ H ₄ Cl-4 ^C 6 ^H 5 .4 -CO ₂ CH ₃ CH ₃ H 0 116-119 182 -C ₆ H ₄ Cl-4 -CH-JCl ₀ -S DJ C. -CO ₂ -Q-CH ₃ CH ₃ H 0 132-134 183 -C ₆ H ₄ Cl-4 -C ₆ H ₄ Cl-4 CH (CH ₃ ) ₂ -CO ₂ CH ₂ CH ₃ CH ₃ H 0 176-178 184 -C ₆ H ₄ Cl-4 ~ ^C 6 ^H 4 ^CF 3 ~ ⁴ H 0 κ 122-124 4s. 185

Table I (continued)

example

No. A

186 187 188 189 190

191 192 193 194 195 196

-C ₆ H ₄ Cl-4

-0 ^, 01-4 0

-C ₆ H ₄ Cl-4

-C _Ä HXl-4 6

-C ₆ H ₄ Cl-4

C ₆ H ₅

-4

-C ₆ H ₄ Cl-4 C ₆ H ₅

-C _c H "Cl-4 6

-C ₆ H ₄ 0CF ₃ -4

-C ₆ H ₄ CO ₂ CH ₂ CH ₃ ^

-CO ₂ CH ₃ -CO ₂ CH ₃ -CO ₂ CH ₃ -CO ₂ CH ₃ -CO ₂ CH ₃

-CO ₂ CH ₃ -CO ₂ CH ₂ CH ₃ -CO ₂ CH ₃ -CO ₂ CH ₃

-CON (CH ₃ J ₂ CH ₃

CH,

CH,

CH,

CH, CH, CH, CH,

-C ₆ H ₄ Cl-4

CH,

-COH (CH ₃ ) ₂

V U Melting point ° C H 0 47-49 H 0 154-155 H 0 122-130 H 0 138-140 H. 0 138-141 H O 188-190 H 0 149-150 H 0 196-198 H 0 135-140 H 0 186-188 H 0 dl

141 Example A

Preparation of 4-chlorophenylbenzene ketone

Into a 2 liter 4-necked flask equipped with a mechanical stirrer and reflux condenser was added 155 g (1.0 mole) of phenylacetyl chloride and 500 ml (4.9 mole) of chlorobenzene. A total of 145 g (1.08 mol) of anhydrous aluminum chloride was added portionwise over a period of 10 minutes. The mixture self-heated to 55 ^° C. and evolved HCl gas over the next 30 minutes # The mixture was stirred for a further 30 minutes at about 50 ^° C. and then poured onto about 500 g of ice and 110 ml of concentrated aqueous HCl. The organic layer (lower) was separated and the aqueous layer was washed with ethyl ether.

/ Wash «The combined organic layers were washed with water, dilute aqueous NaOH and water and then concentrated in vacuo. The resulting crude solid was recrystallized from 2200 ml of hexane,

_ψ wherein 132 g of 4-Chlorphenylbenzy! ketone. Melting point 85 - 90 ° C _{f were} recovered.

Example B

Preparation of 2-phenyl-4'-chlorophenylacrylophenone Into a 1000 ml round bottom flask equipped with a reflux condenser was added 100 g of 4-chlorophenylbenzyl ketone (0.43 mol), 400 ml of methanol, 50 ml of 37% formalin (0.67 f.-y mol), 5 g of piperidine and 5 g of acetic acid. That arise. The mixture was refluxed for 2 hours, concentrated in vacuo, partitioned between ethyl ether and water, washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo to give 98 g of 2-phenyl-1'-chlorophenylacrylophenone, an oil ,

Example C Preparation of 3- (4-chlorophenyl) -4-phenyll-4,5-dihydro-1H-

pyrazole

In a 500 ml round bottomed flask equipped with a reflux condenser, 98 g of 2-phenyl-4 * -chlorophenylacrylophenone (0.40 mol), 200 ml of n-propanol and 50 ml of hydrazine monohydrate (1.0 mol) were mixed Refluxed for 1 hr, cooled slightly, and 100 ml of methanol was added. The resulting solution was cooled in an ice bath and the resulting solid was filtered off and washed twice with cold ethyl ether to yield 55 g of a white solid. Melting point 156 - 162 ° C.

Example D

Preparation of N, 3-bis (4-chlorophenyl) -4-phenyl-4,5-dihydro-IH-pyrazole-1-carboxamide

In a 500 ml Rurid flask, 55 g of 3- (4-chlorophenyl) -4-phenyl-4,5-dihydro-1H-pyrazole were suspended in 250 ml of diethyl ether. The suspension was heated to reflux and 33 g of 4-chlorophenyl isocyanate were added at such a rate as to maintain reflux. After cooling and standing overnight, the precipitated product was filtered off to give 78 g of white solid, m.p. 173-175 ⁰ C,

Example E '

Preparation of 3-dimethylamino-2-niethyl-4'chlorpropiophenon In a 500 ml round bottom flask equipped with a reflux condenser, 84 g 4 chloropropiophenone (0.50 MoI) ,. 50 g of dimethylamine hydrochloride (0.61 mol), 20 g of paraformaldehyde (0.67 mol), 50 ml of ethanol and 10 ml of concentrated aqueous hydrochloric acid mixed. The mixture was refluxed for 18 hours, cooled and partitioned between ethyl ether and water. The ether layer was discarded, and the

aqueous layer was basified with sodium hydroxide and the resulting mixture was extracted twice with fresh ethyl ether. The combined organic layers were washed with brine, dried over magnesium sulfate and concentrated in vacuo to give 105 g of 3-dimethylamino-2-methyl-4- ^f- chloropropiophenone, an oil.

Example F

Preparation of 3- (4-chlorophenol) -4-methyl-4.5-dihydro-1H-pyrazole

Into a 500 ml round bottomed flask equipped with a reflux condenser was added 100 g of 3-diraethylamino-2-methyl-4-chloro - ("*) propiophenone (0.47 mol), 200 ml of n-propanol, 48 Hydrazine monohydrate (0.96 mol) and 5 g of 50% sodium hydroxide were added. The mixture was refluxed for 2 hours. The solvent was removed in vacuo and the mixture was partitioned between methylene chloride and water The organic layer was washed three times with water The organic layer contains 82 g (0.42 mol) of 3- (4-chlorophenyl) -4-methyl-4,5-dihydro-1H-pyrazole, an air-sensitive solid.

Example G

Preparation of N _t 3-Bis-f4-chlorphenvl ') - 4-Methyl-4,5-dihydro l H-pyrazole-1-carboxamide

, To a 500 ml round bottom flask was added 82 g (0.42 mol) of 3- (4-chlorophenyl) -4-methyl-4,5-dihydro-1H-pyrazole dissolved in 300 ml of methylene chloride, and the solution became A solution of 64.5 g of 4-chlorophenyl isocyanate (0.42 mol) in 100 ml of methylene chloride was added at such a rate as to maintain reflux. After stirring for a further 30 minutes, the solvent was removed in vacuo, and resulting oil was crystallized from ethyl ether to give 140 g of N, 3-bis (4-chloro)

phyllo) -4-metyl-4,5-dihydro-1H-pyrazole-1-carboxylate · melting point 139-140 C ·

Example H

Preparation of 5 _{t-Dichlorphenylbenzylcarbinol} 4 In a 1000-ml three-necked flask equipped with RDckflußkühler and addition funnel, was added 8.8 g Magnesiuradrehspäne (0.36 mol) and 400 al of diethyl ether. After activation of the magnesium with 0.02 g of Dod, the mixture was heated to reflux and a solution of 44 g (0.35 mol) of benzyl chloride in ethyl ether was added at such a rate that reflux was maintained. When the reaction subsided, a solution of 50 g of J (0.29 mol) of 3,4-dichlorobenzaldehyde in 75 ml of diethyl ether was added at such a rate as to maintain reflux. After 15 minutes, the reaction was quenched with water and acidified with dilute hydrochloric acid. The organic layer was washed with brine, dried and concentrated in vacuo to give 75 g of 3,4-dichlorophenylbenzylcarbinol which was used without further purification.

Example Σ

Preparation of 3,4-dichlorophenylbenzyl ketone Into a 500 ml round bottomed flask was added 75 g of crude 3,4-dichlorophenylbenzylcarbinol and 300 ml of acetone. The reaction mixture was cooled to ⁰ ° C. and a solution of 20 g of chromium trioxide and 17.25 ml of concentrated sulfuric acid in 60 ml of water was added at such a rate that the internal temperature remained below 5 ^° C. After stirring for a further 15 minutes, the reaction was quenched with 10 ml of isopropanol and the reaction mixture was partitioned between ethyl ether and water. The organic

Layer was washed with brine, dried and concentrated. The resulting crude ketone was crystallized from hexane to yield 51 g of 3,4-dichlorophenyl benzyl ketone.

Example CJ

Preparation of Methvl-3-f4-chXorphenvX) -3-keto-propanoate Into a 1000 ml three-flask equipped with a funnel and condenser was added 15.4 g of 60% sodium hydride (0.63 mol) Sodium hydride was washed twice with hexane and then suspended in 300 ml of tetrahydrofuran and 29 g of dimethyl carbonate (0.32 mol). The reaction mixture was brought to reflux and a solution of 50 g (0.32 : 1 mol) of 4-chloroacetophenone in 50 ml of tetrahydrofuran was added over a period of 30 minutes. After hydrogen evolution ceased, the reaction mixture was cooled and poured onto ice. The aqueous layer was made acidic with hydrochloric acid and extracted with ethyl ether. The organic layer was dried, concentrated and 15 Torr, boiling point 180-205 ⁰ C, distilled to give 40 g of methyl 3- (4-chlorophenyl) -3-keto-propanoate arisen ·

Example 2

Preparation of N, 3-bis-f, 4-chlorophenyl) -4-methyl-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamide

To 2.1 g of diisopropylamine dissolved in 15 ml of tetrahydrofuran and cooled in an ice-salt bath was added 8.0 ml of a 2.7 M solution of n-butyl lithium in hexane, stirring for 5 minutes, adding a solution of 4.2 g of N, 3-Bis (4-chlorophenyl) -4-phenyl-4,5-dihydro-1H-pyrazole-1-earboxamide (Example D) in 15 ml of tetrahydrofuran and the resulting solution was stirred for 15 minutes. This solution became 1.0 ml of iodomethane was added, and after 15 minutes, 1.0 ml of acetic acid was added

The resulting solution was filtered, evaporated in vacuo to give 4.3 g of N, 3-bis (4-chlorophenyl) -4-phenyl-4-methyl-4 , 5-dihydro-lH-pyrazole-1-carboxamide, mp 151-158 ⁰ C, was recovered · the NMR and IR data were consistent with the structure ·

Example 5

Preparation of N, 5-bis-f4-chlorophenyl-4-benzyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide

To 2.1 g of diisopropylamine dissolved in 15 ml of tetrahydrofuran and cooled in an ice-salt bath, 8.0 ml of a 2.7 M solution of n-butyllithium in hexane were added. After stirring for 5 minutes, a solution of 3.4 g of N, 3 was obtained. Bis (4-chlorophenyl) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide (Example G) in 15 ml of tetrahydrofuran and the resulting solution was stirred for 15 minutes. 5 ml of benzylbromide and after 5 minutes 1.5 ml of acetic acid were added. The reaction mixture was partitioned between diethyl ether and water and the organic layer was dried over anhydrous magnesium sulfate. The resulting solution was filtered, evaporated in vacuo to give 3.90 g of N, 3-bis (4-chlorophenyl) -4-benzyl-4-ethyl-4,5-dihydro-1H-pyrazole-1-carboxamide oil, formed · The NMR and IR data were consistent with the structure

Example 34

Preparation of N-f4-3romphenyl) -3- (4-fluorophenyl) -4-butyl-1-4 - met'nyl-4 _> 5-dihydro-1H-pyrazole-1-carboxamide To 2.1 g in 15 ml Tetrahydrofuran dissolved and cooled in an ice salt bath diisopropylamine were added 8.0 ml of a 2.7 M solution of n-Butyllithium in hexane. After stirring for 5 minutes, a solution of 3.7 g of N- (4-bromophenyl) -3- (4-fluorophenyl) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide was added

(prepared from 4-fluoropropiophenone and 4-bromophenyl isocyanate according to one of the analogous methods described above in Examples E, F and G) in 15 ml of tetrahydrofuran, and the resulting solution was stirred for 15 minutes. To this solution was added 1.5 ml of 1 After 10 minutes, 1.5 ml of acetic acid was added. The reaction mixture was partitioned between diethyl ether and water and the organic layer was dried over anhydrous magnesium sulfate. The resulting solution was filtered, evaporated in vacuo and chromatographed to give 2.9 g N- (4-bromophenyl) -3- (4-fluorophenyl) -4-butyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide, an oil which solidified on standing The NMR and IR data were consistent with the structure

Example 51

Preparation of , N, 3-3is (4-chlorophenyl) -N, 4-dirnethyl-4-phegyl ^ / S-dihydro-1H-pyrazole-1-carboxamide To a 100 ml round bottomed flask was added 0.40 g ( 0.01 mol) of 60% sodium hydride. The sodium hydride was washed twice with hexane, and 10 ml of dimethylformamide was added. Subsequently, 2.1 g (0.05 mol) of N, 3-bis (4-chlorophenyl) -4-methyl-4-phenyl-4,5 When hydrogen evolution ceased, 1 ml of dodemethane was added and the mixture was stirred for 1 hour. The reaction mixture was partitioned between ether and water, and the organic layer was dried, filtered, concentrated and chromatographed to give 1.5 g of N, 3-bis (4-chlorophenyl) -N, 4-dimethyl-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamide were. Melting point 132 to 135 ⁰ C. The NMR and IR data were consistent with the structure.

Example 61

Preparation of N, 3-bis (3,4-dichlorophenyl) -4-methyl-4-phenyll-4,5-dihydro-1H-pyrazole-1-carboxamide 3,4-Dichloro -phenylbenzyl ketone was used, essentially following the procedures of the present invention in Examples B, C and D, to prepare N, 3-bis (3-4-dichlorophenyl) -4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxaraid, which was substantially according to the procedures given in Example 2, to give N _t 3-bis (3,4-dichlorophenyl) -4-raethyl-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxaraid, an oil, which became solid on standing. The NMR and IR data were consistent with the structure.

Example 77

Preparation of N _> 3-bis-4- (4-chlorophenyl) -4-carbomethoxy-4-hydroxy-4,5-dihydro-1H-pyrazole-1-carboxamide Method A

To 2.1 ml of diisopropylamine dissolved in 15 ml of tetrahydrofuran and cooled in an ice-salt bath was added 8.0 ml of a 2.7 M solution of n-butyllithium in hexane. After stirring for 5 minutes, a solution of 3.4 g of N, 3-bis (4-chlorophenyl) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide in 7 ml of tetrahydrofuran was added and the resulting solution was stirred for 15 minutes. To this solution was added 1.5 ml of dimethyl carbonate and after 15 minutes 1.5 ml of acetic acid. * The reaction mixture was partitioned between diethyl ether and water, and the organic layer was dried over anhydrous magnesium sulfate. The resulting solution was filtered, evaporated in vacuo to give 3.0 g of N, 3-bis (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide , Melting point 122 ⁰ C. The NMR and IR data were consistent with the structure.

Method B

To 3.4 g of N, 3-bis (4-chlorophenyl) -4-niethyl-4 _# 5-dihydro-1H-pyrazole-1-carboxamide and 1.1 g of diisopropylarain, dissolved in 20 ml of tetrahydrofuran and in a cooled at -20 C acetone bath was cooled; 8.0 ml of a 2.7 M solution of butyllithium in hexane were added. The resulting solution was stirred for 20 minutes and then cooled to -70 ⁰ C · To this solution was added 0.9 ral Methylchlorforraiat · The Reaktionsgeraisch was stirred for 10 minutes and then allowed to warm over a period of 10 minutes at room temperature. The reaction was quenched with 1.0 mL of acetic acid and the reaction mixture was partitioned between diethyl ether and water, and the organic phase was dried over anhydrous magnesium sulfate. The resulting solution was filtered, evaporated in vacuo to give 2.9 g of N, 3 -Bis (4-chlorophenyl) -4-carbomethoxy-4-ethyl-4,5-dihydro-1H-pyrazole-1-carboxamide. The NMR and IR data were consistent with the structure.

Method , C

To 20.0 g of methyl 3- (4-chlorophenyl) -3-keto-propanoate in 100 ml of methanol was added a mixture of 4.7 g of hydrazine monohydrate and 7.6 g of 37% formalin in 50 ml of methanol. The reaction mixture was stirred at room temperature for 1 hr. The methanol was then removed in vacuo and the product was dissolved in 400 ml of methylene chloride and washed five times with 100 rd portions of water. The methylene chloride layer was dried over anhydrous magnesium sulfate and evaporated in vacuo to give 22 g of 3- (4-chlorophenyl) -4-carbomethoxy-4,5-dihydro-1H-pyrazole-1-carboxamide, which were purified in the next reaction without further purification were used.

To 22 g of 3- (4-chlorophenyl) -4-carbomethoxy-4,5-dihydro-1H-pyrazole obtained in the previous reaction was added

200 ml of methylene chloride, and the resulting solution was brought to reflux, whereupon 14.5 g of 4-chlorophenyl isocyanate in 25 ml of methylene chloride were added at such a rate that a controlled reflux was maintained after the mixture was refluxed for an additional 15 minutes when it was cooled, filtered and evaporated in vacuo to give 14 g of N, 3-bis (4-chlorophenyl) -4-carbomethoxy-4,5-dihydro-1H-pyrazole-1-carboxamide (Example 74) , which were purified by column chromatography * The NMR and IR data were consistent with the structure.

To 0.9 ml of diisopropylamine in 10 ml of tetrahydrofuran, which was under a nitrogen atmosphere and cooled to -30 ° C, was added 2.4 ml of a 2.6 M solution of n-butyllithium in hexane. To this reaction mixture was added 1.0 g of 3- (4-chlorophenyl) -4-carbomethoxy-4,5-dihydro-1H-pyrazole in 5 ml of tetrahydrofuran. 0.6 ml CJodmethan was added after stirring ISminütigem ψ, and the mixture was warmed to room temperature and stirred for one hour. Quenching with 1.4 ml of 105% aqueous acetic acid and 5 ml of water and normal ether water treatment gave 1.1 g of N, 3-bis (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-1H- pyrazol-1-carboxaraid, melting point 138-150 ⁰ C. the NMR and IR data were consistent with the structure.

Method D

To 1.3 g (23 mmol) of potassium hydroxide dissolved in 15 ml of dimethyl sulfoxide (DMSO) was added n-butyllithium (21.6 mmol). After stirring for 15 minutes, a solution of 3.4 g (10 mmol) of N, 3-bis (4-chlorophenyl) -4-methyl-4,5-dihydro-IH-pyrazole-1-carboxamide in 15 ml of DMSO was added, and the resulting solution was stirred at 100 ^° C. for 30 minutes. Subsequently, the resulting solution was cooled to 25 ⁰ C. To these

To this solution was added 1.5 ml (17 mmol) of dimethyl carbonate and, after 15 minutes, 1.5 ml (25 mmol) of acetic acid. The reaction mixture was partitioned between methylene chloride and water, and the organic layer was dried over anhydrous magnesium sulfate. The resulting solution was filtered, evaporated in vacuo to give 3.0 g (7x5 mmol) of N, 3-bis (4-chlorophenyl) i-4-carbomethoxy-4- (ethyl-4, 5-dihydroxy) -4- lH-pyrazole-1-carboxaraid, mp 125 ⁰ G, were recovered.

Method E >

To 3.1 ml (23 mmol) dissolved in 15 ml of tetrahydrofuran and cooled to -40 ⁰ C diisopropylamine 8.0 ml of a 2.7 M solution of n-butyllithium (21.6 mmol) was added in five minutes of stirring hexane · After To this was added a solution of 3.4 g (10 mmol) of N, 3-bis (4-chlorophenyl) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide in 7 ml of tetrahydrofuran, and , resulting solution was stirred for 30 minutes · Then the resulting solution was cooled to -65 ⁰ C. To this solution was added 1.5 ml (19 mmol) of methyl chloroformate, and after 15 minutes, 1.5 ml (25 mmol) of acetic acid was added. The reaction mixture was partitioned between diethyl ether and water, and the organic layer was dried over anhydrous magnesium sulfate. The resulting solution was filtered, evaporated in vacuo to give 3.0 g (7.5 mmol) of N, 3-bis (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-1H- pyrazole-l-carboxamide, melting point 125 ⁰ C, were obtained.

Method F.

To 5.3 ml (25 mmol) in 15 ml of 1,2-dimethoxyethane (DME) and dissolved to -40 ⁰ C chilled hexamethyldisilazane were added 8.0 ml of a 2.7 M solution of n-3utyllithium (21.6 mmol) added in hexane. After stirring for 5 minutes, a solution of 3.4 g (10 mmol) of N, 3-bis (4-chlorophenyl) -4-methyl-4,5-di-

hydrochloro-1H-pyrazole-1-carboxamide in 7 ml of DME, and the resulting solution was stirred for 30 minutes. The resulting solution was then cooled to -65 ⁰ C. To this solution was added 1.0 ml (12 mmol) of methyl chloroformate and after 15 minutes 1.0 ml (16 mmol) of acetic acid. The reaction mixture was partitioned between toluene and water, and the organic layer was dried over anhydrous magnesium sulfate. The resulting solution was filtered, evaporated in vacuo to give 3.0 g (7.5 mmol) of N, 3-8is (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-1H-pypazole. 1-carboxamide, melting point 125 ⁰ C, were recovered.

Method G

To 15 ml diethyl ether chilled to -40 ⁰ C 8.0 ml of a 2.7 M solution of s-butyl lithium (21.6 mmol) were added in cyclohexane. After stirring for 5 minutes, a solution of 3.4 g (10 mmol) of N, 3-bis- (4-chlorophenyl) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxanidine in 7 ml of 1.2 -Dimethoxyethane, and the resulting solution was stirred for 10 minutes. The resulting solution was then cooled to -50 ⁰ C. To this solution was added 1.0 mmol (13 mmol) of methyl chloroformate and after 5 minutes 1.5 ml (25 mmol) of acetic acid. The reaction mixture was partitioned between diethyl ether and water, and the organic layer was dried over anhydrous magnesium sulfate. The resulting solution was filtered, evaporated in vacuo to give 3.0 g (7.5 mmol) of N, 3-bis (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole. 1-carboxamide, melting point 125 ⁰ C, were recovered.

Example 92 Preparation of Ν, -3-sis (4-chloro-phenyl) -4-dimethycarbamoyu-1

4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide

In a 3000-necked three-necked flask equipped with a mechanical stirrer,

Thermometer and funnel were added 65 ml

Diisopropylamine (0.47 mol), 155 g (0.45 mol) of N, 3-bis (4-chlorophenyl) -4-hydroxyethyl-4,5-dihydro-1H-pyrazole-1-carboxamide and 1000 ml of tetrahydrofuran · the atmosphere was exchanged with nitrogen and the Geraisch was cooled to an internal temperature of -20 ⁰ C · Subsequently, 375 ml of 2.6 M n-butyllithium in hexane (0.97 mol) was added at such a rate that the internal temperature was kept below -10 ⁰ C · the mixture was stirred for another 30 minutes at -20 ⁰ C and then cooled to -60 ⁰ C, whereupon 45 ml of dimethylcarbamoyl chloride (0.49 mol) was added in one portion · After stirring for 15 minutes was the Reaction with 35 ml of acetic acid and 100 ml of water quenched. After warming to room temperature, the organic layers were separated, dried over magnesium sulfate and concentrated in vacuo. Crystallization from ethyl ether gave 125 g of N, 3-bis (4-chlorophenyl) -4-dimethylcarbamoyl -4-methyl-4,5-dihydro-lH-pyrazol-l-carboxamide id, melting point 194 to 197 ⁰ C, NMR and IR data were consistent with the structure ·

Example 95 .

Preparation of N, 3-bis-4- (chlorophenylV ^ -carboethoxy) - dihydro-1H-pyrazole-1-carboxamide

To 3.2 g of N, 3-bis (4-chlorophenyl) -4,5-dihydro-lH-pyrazol-lcarboxamid, which were dissolved in 20 ml tetrahydrofuran and cooled in an acetone bath maintained at -20 ⁰ C, \ were ; ß 1.5 ml of diisopropylamine and 8.0 ml of a 2.7 M solution of butyl lithium in hexane added · The resulting solution was stirred for 20 minutes and then cooled to -70 ⁰ C · this solution was added 0.5 ml! Ethyl chloroformate added. The reaction mixture was stirred for 10 minutes and then allowed to warm to room temperature over a period of 10 minutes. The reaction was quenched with 1.0 ml of acetic acid, the reaction mixture was partitioned between diethyl ether and water, and the organic layer was dried over anhydrous magnesium sulfate.

The resulting solution was filtered in vacuo to yield 3.3 g of N, 3-bis (4-chlorophenyl) -4-carboethoxy-4,5-dihydro-1H-pyrazole-1-carboxamide and IR data agreed with the structure.

Example 98

Preparation of N.3rBis-4-f4-chlorophenol-4-dithiocarbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide. To 2.3 g in 15 ml of tetrahydrofuran juice and diisopropylarain cooled in an ice-salt bath was added 8 Added 0 ml of a 2.7 M solution of n-butyllithium in hexane. After stirring for 5 minutes, a solution of 3.4 g of N, 3-bis- (4-chlorophenyl) -N-methyl-S-dihydro-1H-pyrazole-1-carboxamide in 7 ml of tetrahydrofuran was added and the resulting Solution was stirred for 15 minutes. To this solution was added 1.5 ml of carbon disulfide, and after 15 minutes, 1.5 ml of methyl iodide was added. Stirring was continued for one hour. The reaction mixture was partitioned between diethyl ether and water and the organic layer was dried over anhydrous magnesium sulfate. The resulting solution was filtered and evaporated in vacuo to give 2.7 g of N, 3-bis (4-chlorophenyl) -4-dithiocarbomethoxy. 4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide were recovered. The NMR and IR data were consistent with the structure.

^ Example 115

Preparation of N, 3-Bis- (4-chlorophenyl) -4-dimethylcarbamoyl-1-methyl-N-acetyl-1S-dihydro-1H-pyrazole-1-carboxamide To a 50 ml round-bottom flask was added 0.45 g of 60 % sodium hydride (0.011 mol) filled. The Natriurahydrid was washed twice with hexane and suspended in 15 ml of tetrahydrofuran. A solution of 2.0 g (0.005 mol) of N, 3-bis (4-chlorophenyl) -4-dimethylcarbamoyl-methyl / S-dihydro-1H-pyrazole-1-carboxamide in 5 ml of tetrahydrofuran was added slowly , As the

1 ml of acetic anhydride was added and the mixture was stirred for 5 minutes. The reaction mixture was partitioned between ethyl ether and brine, dried, concentrated and chromatographed

acetyl- ^ S-dihydro-1H-pyrazole-1-carboxylate nide, an oil, formed. The NMR and IR values were in agreement with the structure Qberein »

Example 130

Preparation of N, 3-3is (4-chlorophenol) -4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-thiocarboxamide 4-Chlorophenylisothiocyanate and 3- (4-chlorophenyl) -4-methyl ~ 4,5-dihydro-lH-pyrazole was used essentially according to the procedures given in Example G to give N, 3-bis (4-chlorophenyl) -4-methyl-4,5-dihydro-1H-pyrazole-1 -thiocarboxaraid, which was used essentially according to the procedure given in Example 77, Method A, to give N, 3-bis- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-1H- to produce pyrazole-1-thiocarboxamide. Melting point 69 to 78 ⁰ C. The NMR and IR data were consistent with the structure ·

Example 138

Preparation of N, 3-bis (4-chlorophenyl) -4-carbomethoxy-4-methyl-N-dimethylcarbamovl-4,5-dihydro-1H-pyrazole-1-carboxamide N, 3-bis- (4-chlorophenyl) 4-Carbomethoxy-4-methyl-4,5-dihydrolH-pyrazole-1-carboxamide was treated with diraethylcarbamoyl chloride essentially according to the procedure given in Example 115 to give N, 3-bis (4-chlorophenyl) -4-carbomethoxy 4-methyl-N-dimethylcarbamoyl-4,5-dihydro-1H-pyrazole-i-carboxaraid, an oil which solidified upon standing for a long time. The NMR and IR data were consistent with the structure.

Example 145 Preparation of N.3-bis-f4-chlorophenyl-4-carbomethoxy-4-

methyl-N "carbomethoxythio" 4,5 "dihydro" 1H "pyrazole-1-carboxamide N _# 3-bis- (4-chloro-phenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-

IH-pyrazole-1-carboxaraid was prepared essentially according to the method described in

Example 115 treated with carbomethoxysulfenyl chloride to give N, 3-bis (4-chlorophenyl) -4-carbomethoxy-methyl-N-carbomethoxythio ^ / S-dihydro-1H-pyrazole-1-carboxamide, a foam * The NMR and IR data were

They were in line with the structure.

Example 149

Preparation of N- (4-trifluoromethvl) -3-f4-chlorophenyl ^ -4-carborothethoxy-4-tnethy1-4,5-dihydro-1H-pvrazole-1-carboxafluoride 4-trifluoromethylphenyl isocyanate and 3- (4-chlorophenyl) - 4-Methyl-4/5-dihydro-1H-pyrazole was used essentially according to the procedures set forth in Example G to give N- (4-trifluoromethyl) -3- (4-chlorophenyl) -4-methyl-4, 5-dihydro-1H-pyrazole-1-carboxaraid, which was used essentially according to the procedure given in Example 77, Method A, with the exception that methyl chloroformate was used as the acylating agent, to give N- (4-trifluoromethyl) To prepare -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide, m.p. 143-146 ° C. The NMR and IR data were consistent with the structure match ·

Example 149 - B

Preparation of H- ( 4-trifluoromethylphenyl) -3- (4-chlorophenol) -4-carbomethoxy-4-fluoro-4,5-dihydro-1H-pyrazole-1-c3-pyramidamide To 3.1 ml (23 mmol) Dissolved in 15 ml of tetrahydrofuran and cooled to -45 ⁰ C diisopropylamine 8.0 ml of a 2.7 M solution of n-butyllithium (21.6 mmol) in hexane were added · After stirring for 5 minutes, a solution of 3.8 G

(10 mmol) N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxaraid in 7 ml of tetrahydrofuran was added, and the resulting solution was allowed to stand for 30 minutes stirred for a long time. "Subsequently, the resulting solution was cooled to -65 ⁰ C. To this solution was added 1.5 ml (19 mmol) of methyl chloroformate, and after 15 minutes, 1.5 ml (25 mmol) of acetic acid was added. The reaction mixture was partitioned between diethyl ether and water, and the organic layer was dried over anhydrous magnesium sulfate. The resulting solution was filtered, evaporated in vacuo to give 4.1 g (9.3 mmol) of N- (4-trifluoromethylphenyl) -3-. (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide, melting point 154 C,

Example 149 - C

Preparation of N-f 4 -trifluoromethylphenyl-3- (4-chlorophenyl) -4-carboethoxy-4-roethyl-4,5-dihydro-1H-pyrazole-1-carboxylate To 0.9 g (23 mmol) on 20 ⁰ C chilled potassium hydride in 15 ml of dimethyl sulfoxide was added a solution of 3.8 g (10 ramol) of N- (4-Trifluormethy! phenyl) -3- (4-chlorophenyl) -4-methy1-4,5-dihydro-LH pyrazole-1-carboxamide in toluene, and the resulting solution was stirred for 45 minutes. The resulting solution was then cooled to -25 ⁰ C. To this solution was added 1.0 ml (13 mmol) of diethyl carbonate and / T ^ s after 60 minutes, 1.5 ml (25 mmol) of acetic acid.

The reaction mixture was partitioned between toluene and water, and the organic layer was dried over anhydrous sodium sulfate. The resulting solution was filtered, evaporated in vacuo to give 4.0 g (9.0 mmol) of N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl-4-carboethoxy-4-methyl-4,5-dihydrochloride). lH-pyrazole-1-carboxamide, melting point 123 ⁰ C emerged.

Example 149 - D

Preparation of N- (4-trifluoromethylphenyD-S-1-chlorophenyl)

nvl) ~ 4 "carbomethoxv-4-Methyl" 4.5 "dihydro-lH" -pvrazol 'l-car-

boxamid

To 3.1 ml (23 mmol) dissolved in 15 ml toluene and cooled to -15 ⁰ C Diisopropylarain 8.0 ml of a 2.7 M solution of n-butyllithium (21.6 ramol) was added in five minutes of stirring hexane · After was a solution of 3.8 g (10 mmol) of N- (4-trifluoro-ethylphenyl) -3- (4-chlorophenyl) -4-methyl-4,5-di, -hydro-1H-pyrazole-1-carboxamide in 15 ml tuplets added and the resulting solution was stirred for 30 minutes · then, the resulting solution to -65 ⁰ C was cooled. To this solution was added 1.5 ml (19 mmoles) of methyl chloroformate, and after 5 minutes, 1.5 ml (25 mmoles) of acetic acid was added. The reaction mixture was partitioned between toluene and water and the organic layer was dried over anhydrous magnesium sulfate. The resulting solution was filtered, evaporated in vacuo to give 4.1 g (9.3 mmol) of N- (4-trifluoromethylphenyl) -3-. (4-chlorophenyl) -4-carbomethoxy-4-methy1-4,5-dihydro-lH-pyrazole-1-carboxamide, mp 154 ⁰ C, were recovered.

Example 149 - E

Preparation of N-f4-trifluorofluorophenyl ") - 3- (4-chlorophenyl)

nvl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-car-

boxamide <.

To 0.9 g (22 mmol) of potassium hydride suspended in 15 ml of toluene and cooled on OC was added a solution of 3.8 g (10 mmol) of N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-methyl 4,5-dihydro-1H-pyrazole-1-carboxamide in 7 ml of toluene, and the resulting solution was stirred for 60 minutes. The resulting solution was subsequently added

-45 ⁰ C cooled. To this solution was added 1.0 ml (13 mmol) of methyl chloroformate, and after 5 minutes, 1.0 ml (16 mmol) of acetic acid was added. The reaction mixture was partitioned between toluene and water, and the organic layer was dried over anhydrous magnesium sulfate. The resulting solution was filtered, evaporated in vacuo to give 4.0 g (9.0 mmol) of N- (4-trifluoromethylphenyl) -. 3 -. (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-lH-pyrazole-1-carboxamide, mp 154 ⁰ C, emerged.

Example 149 - F

Preparation of N- (4-trifluoromethvlphenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide. To 1.3 g (25 mmol) at 50 ⁰ C stirred sodium methoxide in 15 ml of dimethyl sulfoxide, a solution of 3.8 g (10 mmol) of N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-raethy1-4,5-dihydro-lH- pyrazole-1-carboxamide in 15 ml of xylenes, and the resulting solution was stirred for 60 minutes. Subsequently, the resulting solution was cooled to OC. To this solution was added 1.0 ml (13 mmol) of dimethyl carbonate and after 15 minutes 1.5 ml (25 mmol) of acetic acid. The reaction mixture was partitioned between xylenes and water, and the organic layer was azeotropically dried. The resulting solution was evaporated in vacuo to give 4.0 g (9.0 mmol) of N- (4-trifluoroethylphenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-1H Pyrazole-1-carboxamide, melting point 154 ⁰ C emerged.

Example 150 Preparation of N, 3-bis (4-chlorophenyl) -4-carbomethoxy-4-

Methyl-N-f2-nitrophenylsulphenyl ') - 4,5-dihydro-lH-pyrazol-l-

carboxamide

N, 3-Bis- (4-chlorophenyl-4-carbomethoxy-4-methyl-4,5-dihydrolH-pyrazole-1-carboxamide was prepared essentially according to the method described in

Example 115 is treated with 2-nitrophenylsulfenyl chloride to give N, 3-bis (4-chlorophenyl) -4-carbomethoxy-4-methyl-N- (2-nitrophenylsulfenyl) -4,5-dihydro-IH-pyrazole -l-carboxamide was recovered. The NMR and IR data were consistent with the structure »

Example ISO Preparation of N, 3-bis (4-chlorophenyl) -4-carbomethoxy-4-

fflethy _[ l-N- (l-carbomethoxy-prop-2-yl-thio) -4,5-dihydro-LH

pyrazole-1-carboxamide

N, 3-Bis (4-chlorophenyl) -4-carbomethoxy-4-methyl-4 _# 5-dihydro-IH-pyrazole-1-carboxamide was prepared essentially according to the procedure given in Example 115 with (1-carbomethoxy-prop 2-yl) disulfide, whereby N, 3-bis (4-chlorophenyl) -4-carboroethoxy-4-ethyl-N- (1-carbomethoxy-prop-2-yl-thio) -4,5-dihydro -lH-pyrazole-1-carboxamide was recovered. The NMR and

IR data was consistent with the structure. Example 185 - A

Preparation of N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl-4-carboethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide To 0.9 g (23 mmol) in 15 ml A solution of 4.0 g (10 mmol) of N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-methyl-4,5-dihydro-1H-4-methyl-4,5-dihydro-1H, dissolved in anhydrous ammonia and cooled to -40C. pyrazol-l-carboxamide added in 7.ml tetrahydrofuran, and the resulting solution was stirred minutes. Subsequently, the resulting solution was cooled to -65 ⁰ C. to this solution was added 1.5 ml (12.5 ramol) of diethyl carbonate and after 15 The reaction mixture was partitioned between diethyl ether and water and the organic layer was dried over anhydrous magnesium sulfate. The resulting solution was filtered, evaporated in vacuo to give 4.2 g

> i

(9.0 ramol) of N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-carboethoxy-4-methyl-4,5-dihydro-lH-pyrazol-l-carboxaraid, melting point 124 ⁰ C won, were ·

Example 185 - B

Preparation of N- (4-trifluoromethylphenvl ') - 3-f4-chlorophenyl) -4-carboethoxy-4-methyl-4 _# 5-dihydro-1H-pyrazole-1-carboxafluid To 3.1 ml (23 mmol) in 15 8 ml of a 2.7 M solution of n-butyllithium (21.6 mmol) in hexane were added to ¹ ml of toluene and diisopropylamine cooled to -45 ° C. After stirring for 5n hours, a solution of 3.8 g ( 10 mmol) of N- (4-trifluoromethylphenyl) -3- (4-chlorophenyl) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxaraid in 10 ml of toluene, and the resulting solution became Stirred for 30 minutes. The resulting solution was then cooled to -65.degree. To this solution was added 1.5 ml (15 mmol) of ethyl chloroformate and after 15 minutes 1.0 ml (16 mmol) of acetic acid. The reaction mixture was partitioned between toluene and water, and the organic layer was dried over anhydrous magnesium sulfate. The resulting solution was filtered, evaporated in vacuo to give 4.1 g (9.0 mmol) of N- (4-trifluoromethylphenyls 1-3 - (4-chloro-phenyl) -4-carboet hoxy-4-me thy 1-4, 5-dihydro ro-IH-pyrazole-l-carboxaraid, melting point 124 ⁰ C, were obtained.

Example 186 - A

Preparation of M- (4-trifluoromethoxyphenvl) -3- (4-chlorophenyl) -

4-carboroethoxy-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide. Potassium t-butane dissolved in 2.5 g (23 mmol) in 15 ml of t-butanol.

A solution of 4.0 g (10 mmol) of N- (4-trifluoromethoxyphenyl) -3- (4-chlorophenyl) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxaride in 7 ml of tetrahydrofuran was added and the resulting solution was stirred at 60 ⁰ C for 30 minutes. Subsequently, the resulting solution was at 25 ⁰ C.

cooled. To this solution was added 1.0 mL (12.5 mmol) of methyl chloroformate and after 15 minutes 1.0 mL (16 mmol) of acetic acid. The reaction mixture was partitioned between ethyl acetate and water and the organic layer was dried over anhydrous magnesium sulfate The solution was filtered, evaporated in vacuo to give 4.1 g (9.0 mmol) of N- (4-trifluoromethoxyphenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro-1H Pyrazole-lcarboxamid, melting point 47 ⁰ C, were obtained.

Example 186 - B

Preparation of N- (4-trifluoromethoxyphenvl) -3-f4-chlorophenyl ') - 4-carboethethoxy-4-methyl-4, S-dihydro-1H-pyrazole-1-carboxamide

To 3.1 ml (23 mmol) dissolved in 15 ml of tetrahydrofuran and cooled to -40 ⁰ C diisopropylamine 8.0 ml of a 2.7 M solution of n-butyllithium (21.6 mmol) were added in hexane '· After five minutes of Stirring was added a solution of 4.0 g (10 mmol) of N- (4-trifluoromethoxyphenyl) -3- (4-chlorophenyl) -4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide in 7 ml of tetrahydrofuran added and the resulting solution was stirred for 30 minutes · then the resulting solution was cooled to -65 ⁰ C. To this solution was added 1.0 ml (12.5 mmol) of methyl chloroformate and after 15 minutes 1.0 ml (16 mmol) of acetic acid. The reaction mixture was partitioned between diethyl ether and water and the organic layer was dried over anhydrous magnesium sulfate. The resulting solution was filtered, evaporated in vacuo to give 4.1 g (9.0 mmol) of N- (4-trifluoro-methoxyphenyl) -3- (4-chlorophenyl) -4-carbomethoxy-4-methyl-4,5-dihydro -LH-pyrazole-l-carboxamide, melting point 47 ⁰ C emerged.

Surprisingly, many of the compounds according to the invention have a better pesticidal activity than the known dihydropyrazoles. The compounds according to the invention thus represent a real enrichment of the field.

For example, certain l-substituted-4-substituted-4-dihydro-1H-pyrazoles of the present invention are present at a level of from about 2 ppm (parts per million) to about 15 ppm against the "Southern Army Worm" (Spodoptera eridania); from about 0.1 ppm to about 10 ppm against the Mexican bean beetle ( Epilachna varivestis ) and from about 1 ppm to about 10 ppm against the Baura bean capsule beetle ( Anthonomus grandis grandis ) *.

Because of their strong initial pesticidal activity and excellent residual pesticidal activity, the compounds of the present invention can be used in low doses for pest control. The dosage will depend on a number of factors, for example, the active ingredient used, the pest species, the formulation used, the condition of the pest-infested crop, and the prevailing weather conditions. Generally, one dose can be used for pest control in agriculture and horticulture corresponding to about 0.1 grams to about 1000 grams of active ingredient per hectare,

, and a dose of about 5 grams to about 200 grams of active ingredient

^w per hectare is preferred.

Representative pests that can be controlled by the compounds of the invention include:

,

American cockroach ( Periplanta americana )

Bean Leaf Beetle ( Cerotoma trifurcata ) "Bean Leaf Beetle" Bean Leaf Roller ( Urbanus proteus ) "Bean Leaf Roller" Black Carpenter Ant ( Camponotus Pennsylvanicus ) "Black

Roßameise "

Caterpillar of the Ypsilene Owl ( Agroti.s ipsilon ) ·; 'Baurawollkapselkäf er C Anthonotnus grandis gjandis' ) Colorado beetle ( Lepitinotarsa decetnlineata ) Fall Armyworm ( Spodoptera frugiperda ) 'Herbstheerwurm' German cockroach ( Blatella cjermanica )

Green Dune Beetle ( Cotinis nitida ) "Green Ounic Beetle" House Cricket ( Ancheta domesticus ) 'Housefly ( Musca domestica )

Mexican Bean Beetle ( Epilachna varivestis ) "Mexican

Bean beetle "

Potato Leaf Hopper ( Empoasca fabae ) "Potato Leaf Hopper" Red Harvester Ant f Poffonomyrfflex barbatus ) "Red Harvest Ant" Red Imported Fire Ant ( Solenopsis invicta ) "Red Knotted Ant"

Redlegged Grasshopper ( Melanopus femurrubrum ) " Rotbeiniqe

Field grasshopper "

Southern Armyworm ( Spodoptera eridania ) "Southern Army"

worm"

Southern Corn Rootworm ( Diabrotica undecimpunctata howardi )

"Southern Corn Rootworm" Tobacco Budworm (" Heliothis virescens ") "Tobacco Budworm"

The compounds of the invention can be used for practical applications in the form of compositions or formulations. In these compositions and formulations, the active ingredient is mixed with conventional inert (i.e., plant tolerant and / or pest control) pesticidal diluents or extenders such as solid carrier material or liquid carrier material useful in conventional pesticide compositions or formulations. On request you can

also additives such as surfactants, stabilizers, antifoams and antidrift agents are used.

Examples of compositions and formulations according to the invention are aqueous solutions and dispersions, oily solutions and oil dispersions, pastes, dusts, wettable powders, emulsifiable concentrates, free-flowing agents, granules, baits, invert emulsions, aerosol compositions and incense candles.

Injectable powders, pastes, flowables and emulsifiable concentrates are concentrated preparations which are diluted with water before or during use.

Bait agents are preparations which generally contain a food or other insect attractant substance and at least one lethal or non-lethal toxin. Lethal toxins kill insects when they eat the bait agent, while non-lethal toxins kill the behavior and physiology of the insect to combat it change·

Invert emulsions are mainly used for air application, where large areas are treated with a comparatively small amount of preparation. The invert emulsion can be prepared in the sprayer just before and even during the spraying process by emulsifying water in an oil solution or an oil dispersion of the active ingredient becomes

Compositions and formulations are prepared in a known manner, for example by stretching the active compounds with conventional dispersible liquid diluents and / or dispersible solid carriers.

for pesticides, optionally using carrier excipients, e.g. For example, where water is used as a diluent, organic solvents can be added as co-solvents. The following are mainly suitable for use as conventional carrier vehicles for this purpose: Aerosol propellant which are gaseous at normal temperatures and pressures, such as halogenated hydrocarbons, e.g. B, dichlorodifluoromethane and trifluorochloromethane, as well as butane, propane, nitrogen and carbon dioxide; inert dispersible liquid diluents including inert organic solvents such as aromatic hydrocarbons (e.g., benzene, toluene, xylene, alkylnaphthalene, etc.), halogenated, especially chlorinated, aromatic hydrocarbons (eg, chlorobenzenes, etc.), cycloalkanes (z Cyclohexane, etc.), paraffins (ζζΒΒ petroleum or mineral oil fractions), chlorinated aliphatic hydrocarbons (eg, methylene chloride, chloroethylene, etc.), vegetable oils (eg, soybean oil, cottonseed oil, corn oil, etc.). Alcohols (· ζ · Β methanol, ethanol, propanol, butanol, glycol, etc. _#) as well as ethers and esters thereof (ζ · Β · GIycolmonomethylether etc #), amines (eg # ethanolamine, etc.) (, amides ζ · Β · dimethylformamide etc .), Acetonitrile, ketones (ζ · Β · acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.) and / or water; solid carriers including ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly dispersed silicic acid, alumina and silicates; Solid carriers for granules include crushed and classified natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic flours, and granules of organic material such as sawdust, coals and granules.

kusnut shells, corncobs and tobacco stalks. The following may be considered primarily for use as conventional carrier adjuvant: emulsifiers such as cationic and / or nonionic and / or anionic emulsifiers (e.g., polyethylene oxide esters of fatty acids, polyethylene oxide ethers of fatty alcohols, alkyl sulfates, alkyl sulfonates, aryl sulfonates, albumin hydrolysates, etc., and especially alkylaryl polyglycol ethers , Magnesium stearate, sodium egg acetate, etc.), and / or dispersants such as lignin, liquors, methylcellulose, etc.

Adhesives such as carboxymethyl cellulose and natural and synthetic polymers in the form of. Powders, granules or latexes such as gum arabic, polyvinyl alcohol and polyvinyl acetate can be used in the formulations.

If desired, colorants may be used in the compositions and formulations containing the compounds of the present invention such as, for example, inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes and trace salts such as salts of iron, manganese, boron , Copper, cobalt, molybdenum and zinc.

The active compounds according to the invention can be used alone or in the form of mixtures with one another and / or with such solid and / or liquid dispersible carrier vehicles and / or with other known compatible active substances, in particular crop protection agents such as other arthropodicides, nematicides, fungicides, bactericides, rodenticides, herbicides, fertilizers, Growth regulants, synergists, etc., or in the form of certain dosage preparations prepared therefrom for specific applications such as solutions, emulsions, suspensions, powders, pastes and granules based on

168 are ready for use, these are used

As regards commercial preparations, they are generally mixtures of carrier compositions in which the active substance is present in an amount of substantially between about 0.001 and 99% by weight and preferably between about 0.005 to 90 parts by weight of the mixture Use or field-appropriate carrier composition mixtures generally contain the active compound in an amount of substantially between about 0.00001 to 95% by weight, preferably 0.00005 to 90% by weight of the mixture. The invention thus comprises total compositions comprising mixtures of a conventional dispersible carrier as (1) a dispersible inert finely divided carrier solid and / or (2) a dispersible carrier liquid such as an inert organic solvent and / or water, preferably a surfactant amount of a carrier vehicle adjuvant (ζζΒ) a surfactant such as an emulsifier tel and / or dispersing agent) and an amount of active compound effective for the purpose in question

The active compounds may be applied by conventional methods as insecticidal sprays, such as conventional dilute high dilution spray, low dilution spray, ULV spray, spray, aerosol and dust spray. When low dilution applications are required, a solution of the compound is usually used. In the ULV process, a liquid composition containing the active compound is usually applied as a spraying agent (e.g., mist) by means of a sputtering apparatus in finely divided form (average particle size).

size of about 50 to about 100 microns or less) using airborne crop spraying methods. Typically, only a few liters per hectare are needed, and often amounts of about 15 to 1000 g / ha, preferably about 40 to 600 g / hectare sufficient · In the ULV process, it is possible to use highly concentrated liquid compositions with the liquid carrier vehicles containing from about 20 to about 95% by weight of active compound.

In addition, the invention encompasses methods of selective pest control or control which involve applying to a particular controlled or toxic amount (ζ · Β of a pesticidally effective amount) of the particular active compound of the invention, alone or together with a carrier vehicle as described above, at least one of: b) its habitat (ie the place to be protected, eg a growing crop or an area on which the crop is to be cultivated). The finished formulations or compositions are used in a conventional manner, for example by spraying, atomizing, evaporating, spreading, dusting, blasting, spraying, sprinkling, pouring, smoking, dry fertilizing, wet fertilizing, wet fertilizing, sludge thickening, top crusts and the like.

It will, of course, be understood that the concentration of the particular active compound used in admixture with the carrier vehicle depends on such factors as the type of equipment used, the method of application, the area to be treated, the types of pests to be controlled and the degree of infestation , Therefore, it is possible in special cases to exceed or fall short of the aforementioned concentration ranges.

Granulated preparations are prepared, for example, by taking up the active ingredient in a solvent and using the resulting solution, as may be the case in the presence of a binder, around a granulated carrier material, never porous granules (eg pumice and attaton) or mineral nonporous Granules (eg dried coffee grounds and shredded tobacco stalks) to be impregnated

A granulated preparation (often referred to as a "pellet") may optionally be prepared by pressing the active ingredient together with powdered minerals in the presence of lubricants and binders, and grinding and molding the composite to the desired grain size.

Dusting agents can be obtained by intimately mixing the active ingredient with an inert solid support material in a concentration of about 1 to about 50% by weight. Examples of suitable solid support materials are talc, kaolin, whistling clay, diatomaceous earth, dolomite, gypsum, chalk, bentonite attapulgite and colloidal SiO ₂ or mixtures of these and similar substances. Optionally, organic support materials such as ground walnut shells may be used.

Injection powder and flowable preparations are prepared by mixing about 10 to about 99 parts by weight of a solid inert carrier such. The above carrier materials comprise from about 1 to about 30 parts by weight of active ingredient, from about 1 to about 5 parts by weight of a dispersing agent such as the lignosulfonates or alkylnaphthalene sulfonates known for this purpose, and preferably from about 0.5 to about 5 parts by weight of a wetting agent such as fatty alcohol sulfates or alkylarylsulfonates of fatty acid condensation products.

 A

 Ί

For the preparation of emulsifiable concentrates, the active compound is dissolved or finely divided in a suitable solvent, the solvent preferably being poorly miscible with water and an emulsifying agent being added to the resulting solution. Examples of suitable solvents are xylene, toluene, high-boiling aromatic petroleum distillates, for example solvent naphtha , Distilled tar oil and mixtures of these liquids. Examples of suitable emulsifying agents are alkylphenoxypolyglycol ethers, polyoxyethylene sorbitan esters of fatty acids or polyoxyethylene sorbitol esters of fatty acids. The concentration of the active compound in these emulsifiable concentrates is not strictly limited and may vary between about 2 and about 50 mass. Another suitable liquid highly concentrated primary composition as an emulsifiable concentrate is a solution of the active ingredient in a liquid that is readily miscible with water, for example acetone, the egg dispersing agent and, if appropriate, a mixing agent are added. If such a primary composition is diluted with water shortly before or during the spraying process, an aqueous dispersion of the active ingredient is obtained.

An aerosol preparation according to the invention is obtained in the usual way by mixing the active ingredient or a solution thereof in a suitable solvent into a volatile liquid suitable for use as a propellant, for example as a mixture of chlorine and fluorine derivatives of methane and ethane. Incense or incense, which produces pesticidal smoke upon firing, is obtained by ingesting the active ingredient in a flammable mixture containing, for example, a sugar or a wood, preferably in ground form, as a fuel, a substance in support of combustion such as ammonium nitrate or potassium chlorate, and

In addition, it may contain a combustion retarding substance, for example kaolin, bentonite and / or colloidal silica.

A bait agent contains a food or other pest-craved substance, a carrier, the poison, and may optionally contain other substances commonly used in preparations of this kind, such as a preservative for preventing bacterial or fungal growth, a waterproofing agent for preventing disintegration moist conditions and dyes or colorants as described above ·

In addition to the abovementioned constituents, the preparations according to the invention may also contain other substances used in preparations of this type.

For example, a lubricant such as calcium stearate or magnesium stearate may be added to a wettable powder or mixture to be granulated. In addition, for example, adhesives such as polyvinyl alcohol cellulose derivatives or other colloidal materials such as casein may be added to increase the adhesiveness of the pesticide to the surface to be protected.

Representative illustrative examples of compositions and formulations containing compounds of the invention are listed below as Examples K through S.

Example 1 <

Granules ingredient toxin

Triton ^R X-305 (binder) Agsorb ^R 24/48 (extender)

Preparation: The toxin and Triton X-305 are dissolved in methylene chloride and the mixture is added to the Agsorb with constant mixing. »Then the methylene chloride is allowed to evaporate.

Dimensions% 25 0 25 0 50 99

, L _ component Example L Dimensions% Toxic Talc dusts 1.0 99.0

Preparation: The toxin is dissolved in an excess of acetone and the talcum soaked with the mixture. Then the acetone is allowed to evaporate.

Example M Spray powder Component Massel

---------, _. , it

Toxic substance 25,0

Toxic substances 6,3

Duponal WA Dry (wetting agent) 2.0

Reax 45A (dispersant) 5.0

Bard clay (extender) 31.7

HiSil ^R 233 (extender) 30.0

Production: The toxin is absorbed by the bard tone and HiSiI carriers. Then Duponal and

Reax added, and the gesarate dry mixture is mixed until it is homogeneous. The composition is then raicronized to a fine particle size,

Example N Emulsifiable concentrate Constituent massel

Toxic substance 13.5 Toxic substances 1.5

Sponto ^R 232T (emulsifier) 6.0

Sponto ^R 234T (emulsifier) 4.0

Cyclohexanone (solvent) 22.5

Tenneco ^R 500-100 (solvent) 52.5

manufacture; All ingredients are mixed together with constant stirring until a homogeneous clear solution is obtained.

Example 0

Aeros ol

Constituent massel

Toxic substance 0,5

Freon 12 99.5

Preparation: The ingredients are mixed and packaged under pressure in a suitable container equipped with a safety syringe valve.

Example P

Incense or incense powder ingredient

Toxic substance 1.0

Wood dust 96.0

Strength 3.0

Preparation: Toxin, wood dust and starch are mixed together and then formed into a candle using a small amount of water to activate the starch.

Example Q bait

Method A mass component

Toxic substance 1.00 Wheat bran (carrier and lure) 89.95

Haissirup (lure) 7,00

Λ corn oil (lure) 2.00

Kathon ^R 4200 (preservative) 0.05

Production: Corn oil and corn syrup are added to aer 1 / Veizenkleie with appropriate mixing. The toxin and Kathon are premixed with an excess of acetone, and this solution is added to the wheat bran base with continued mixing. Then the acetone is allowed to evaporate,

Method B

Ingredient mass%

Toxic substance ν 0,06

Granulated sugar (carrier and attractant) 99,94

Example R

pellet

As per Example Q, Method A, with the following addition: The bait composition is molded into 1/4 inch diameter and 3/8 inch long pellets using a suitable die presser.

Example S Flowable agent Constituent massel

Toxic substance 25,0 Toxic substances 6,3

Duponal WA Dry (wetting agent) 2.0 Reax ^R 45A (dispersing agent) 5.0

HiSil ^R 233 (extender) 30.0 Kelzan ^R (thickener) 0.5

Water 31.2

Preparation: The toxicant is taken up by the HiSiI® vehicle. Duponal and Reax are then added and the whole dry mixture is mixed until homogeneous.

The composition is then micronized to a fine particle size. The resulting powder is suspended in water and Kelzan is added

Compositions and formulations according to the invention may also contain known pesticidal compounds. This extends the spectrum of activity of the preparation and synergism can be effected.

The following known insecticidal, fungicidal and acaricidal compounds are suitable for use in such a combined preparation.

Insecticides like:

1. Chlorinated hydrocarbons, for example, 2,2-bis (p-chlorophenyl) -l, l, l-trichloroethane and hexachloroepoxyoctahydrodimethanonaphthalene;

2. carbamates, for example N-methyl-1-naphthylcarbamate;

3. dinitrophenols, for example, 2-methyl-4,6-dinitrophenyl and 2- {2-butyl) -4,6-dinitrophenyl-3,3-dimethylacrylate;

4. organophosphorus compounds such as dimethyl 2-methoxycarbonyl-1-niethylvinyl phosphate, 0,0-diethyl-O-p-nitrophenyl phosphorothioate; N-Monomethylamide of 0,0-dimethyldithiophosphorylacetic acid j

5 * diphenyl sulfides, for example p-chlorobenzyl or p-chlorobenzyl sulfide and 2,4 _f 4 ^f -5-tetrachloride diphenyl sulfide;

6 »diphenyl sulfonates, for example p-chlorophenylbenzenesulfonate;

7 · methylcarbinols, for example 4,4-dichloro-1-trichloromethylbenzhydrol;

8. quinoxaline compounds such as ethylquinoxaline dithiocarbonate; 9 · Amidines such as N '- (4-chloro-O-tolyl) -N, N-diethylformamidine;

10 »Pyrethroids like Allethrin;

11 · Biological agents such as Bacillus thuringiensis preparations; 12 · organotin compounds such as tricyclohexyltin hydroxide;

Fungicides like:

Mercury-containing organic compounds such as phenylmercuric acetate and methylmercury cyanoguanide;

14 · organotin compounds, for example triphenyltin hydroxide and triphenyltin acetatej

15 * Alkylenebisdithiocarbamates, for example zintfethylenebisthiocarbamate and manganoethylenebisthiocarbamate, and also ''. , '

16. 2,4-dinitro-6- (2-octylphenyl crotonate), 1-bis (dichloroamino) phosphoryl-3-phenyl-5-amino-1, 2-4-triazole, 6-methylquinoxaline-2,3-dithiocarbonate, 1,4-Oithioantraquinone-2,3-dicarbonitrile, N-trichloromethylthiophthalimide, N-trichloromethylthiotetrahydrophthalimide, N- (1,1,2,2-tetrachloroethylthio) -tetrahydrophthalimide, N-dichlorofluoromethylthio-N-phenyl-N'-dimethylsulfonyldiamide and tetrachloro is opht ha loni tr il.

Biological effectiveness

It has been found by biological examination and evaluation that the compounds according to the invention possess pesticidal activity and are able to control larvae and adult forms of pests, especially the "Mexican bean beetle", "Southern armyworm" and boll weevil the compounds according to the invention are active against pyrethroid-resistant pests such as Colorado beetle and housefly

In evaluating the pesticidal activity of the compounds according to the invention, the following test methods were used · Evaluations were carried out on the following insects:

Trivial name Latin name

Mexican Bean Beetle ("Mexican ψ bean beetle") Epilachna variyestis

Southern Armyworra ("Southern

HeerwurnT) Spodoptera eridania

Cotton boll weevil Anthonomus grandis grandis

A test solution containing 600 parts per million (ppm) was prepared by dissolving the test compound in a solvent (acetone: methanol, 1: 1), adding a surfactant, and then water to produce an acetone: methanol: water system of 10 : 10: 80 Prepared A 1: 1 mixture of an alkylarylpolyether alcohol (sold under the trademark Triton X-155) and an n-modified phthal glycerol alkyl resin (sold under the trademark Triton * 8-1956) was added in an equivalent amount of 1 ounce per 100 Gallons of test solution used as a surfactant ·

Analogous solutions are prepared by serially diluting the 600 ppm test solution with water and surfactant to give concentrations of 150; 38; 10; 2.5; 0.6; To obtain 0.15 and 0.038 ppm. Not all compounds are tested at each of the various concentrations listed above. Certain concentrations of a particular compound tested are evaluated by results obtained in a less definite range-finding trial. The test concentrations of a compound are those which are most likely to be the reaction of a particular test insect to different doses of a particular compound

For the test with the "Mexican Bean Beetle" and the "Southern Army Worm", seedlings of the lima bean ( Phaseolus limensis Var.Woods ' Prolific) were sprayed in 3-inch pots to run down with the test solutions using a DeViI-bite nebulizer 20 psig (1 psig = 7.031 ♦ 10 at top pressure, d.s.b.). When the plants were dry, each was placed in a plastic box (7.5 inches long χ 5.25 inches wide χ 3.75 inches deep). Each box was then filled with 10 third instar larvae of the "Mexican Bean Beetle" or "the "Southern army worm" occupied · The box was then closed with a lid equipped with protected ventilation holes ·

Cotton seedlings (G pssyρium hirsutum Var · Acala) are treated in the same way for the cotton boll beetle . Ten young adult cotton boll beetles are placed in each plastic box containing the treated plant which has been allowed to dry. The boxes are then closed as above.

  , ,

All boxes containing the treated plants are stored consistently under fluorescent light at 80 + 5 ^° F on open shelves throughout the exposure period. The plants are watered as needed and replaced with untreated plants when completely depleted, such as in ineffective treatments or untreated control plants the case would be *

Six days after treatment, mortality is determined in percent for each test species and spray concentration. The following table (Table II) gives for representative compounds of the invention the mortality data as a percentage of killed insects at the indicated concentration.

Table II MMMWMM-lllllWillWI · fc *. Biological evaluation

,, . , ; , , Test insect,, -, '-', ·. ';

"Mexican" Southern Cotton Capsule BeisDiel Bean Beetle "Army Beetle" Beetle No * 10 ppm 2.5 ppm 38 ppm 10 ppm 53 ppm 10 ppm

2 100 70 100 100 100 100 16 60 40 90 0 100 90 66 100 10 100 100 100 80 77 100 90 a World Cup WW 100 100 100 84 90 80 100 90 90 20 92 ww 100 100 20 100 90 105 , 100 100 100 90 100 100 114 100 100 100 80 100 100 123 100 80 WW Ml 70 100 100 124 100 100 100 ^b 100 ^b , 100 100 141 MWWW 100 100 100 100 100 143 - 100 mm WW 100 100 149 - VAT * 100 ... 100 - 152 - 100 100 100 100 100 186 100 100 100 90

181 To Table II

a) Not tested at the specified concentration ·

b) The originally applied maximum concentration was 2.5 ppm and did not kill the insects. The "Southern Army Worm" experiment was repeated, with the results reported, and at 2.5 ppm, the destruction was again O % .

c) The maximum concentration applied was 2.5 ppm, bringing a 100 . % ± destruction.

It is understood that this description and the examples of, a more detailed explanation serve and not limitation and that various modifications and changes may be made without © ind departing from the essence and scope of the invention as defined in the appended claims, ·

Claims (33)

claims; V is hydrogen, (Co-Gg) -cycloalkyl, unsubstituted or. substituted aryl or R -Q; Y represents lower straight or branched chain, unsubstituted or substituted (C 1 -C 6) -alkyl, unsubstituted or substituted aryl or a group of the formula -C-G in which X represents O, S or N-Q; Z is hydrogen, (Co-Cg) -cycloalkyl, unsubstituted or substituted aryl or R-Q, with the proviso that Z is not hydrogen, when Y is alkyl or aryl and Z is not methyl, vs Y is methyl; q is hydrogen, halogen, cyano, nitro, OR, R OR, COR 41 123 12 12 12, ag, ya, ir,,, 2, OR4OR1, CR1R2R3, CONR1R2, NR1R2, NR1COR2, N (COR1) COR2, CSR1, SR1 , SOR1, SO2R1, NR1SOR2, R4SR1, OR4SR1, SR4SR1, SNHSR1, SNHSO2R1, CONHSR1, OCOR1, R1, C (= NR1) R2, COR1, No, OSO2R1, NR1SO2R2, NR1CSR2, alkenyl (CR1 = CR2R3), alkynyl ( CSCR) or aryl; 3 "1 ^ C-R, wherein Σ represents O or S of claim 26, cyano, lower (C ₁ -C 4) alkylheteroalkyl wherein the substituent or alkyl moiety is lower (C ₁ -C 4) alkoxy, lower (C ₁ -C 4) alkylsulfenyl, unsubstituted or substituted phenylsulfenyl, lower (C ₁ -C *) - carboalkoxy, cyano or lower (C 1 -C 4) -alkylheteroalkyl; Υ lower straight-chain or branched-chain, unsubstituted or substituted (Cj-Cg) alkyl or unsubstituted or substituted phenyl; and Z is lower (C 1 -C 4) alkyl or unsubstituted or substituted phenyl, provided that Z is not methyl, where Y is methyl. 1 ? 3 4 A, U, Y, Z, Q, R, R, R, R, R, G and η have the meaning explained in claim 3 and
B is substituted phenyl; and Y is hydrogen, unsubstituted or substituted phenyl or RQ; and agronomically acceptable salts thereof. 1 P 3 4. A, B, ü, V, Q, R, R, R, R, R, G and η are as defined in claim 1, and Il Y is a group of the formula -C-G wherein X is O, S or H-Q; and Z is hydrogen, (C 1 -C 12 cycloalkyl, unsubstituted or substituted aryl or R -Q; and agronomically acceptable salts thereof. 2. Composition according to claim 1, characterized in that Composition according to Claim 2, characterized in that R, R ¹ , R ² , R ^ and R, G, Q and η are as defined in claim 2 Have meaning and A is unsubstituted or substituted phenyl; B is unsubstituted or substituted phenyl; ü is 0 or S; Y is hydrogen, (C, -Cg) -cycloalkyl, unsubstituted or substituted phenyl or R -Q; Y is a group of formula Jq ^ q where Σ is Ό or S; and Z is hydrogen, (C 1 -C 4) cycloalkyl, unsubstituted or substituted phenyl or RQ;
and agronomically acceptable salts thereof. 4Z is unsubstituted or monosubstituted phenyl or R-Q with the proviso that Z is not hydrogen and Z is not methyl when Y is methyl; and agronomically acceptable salts thereof · 4. Z is unsubstituted a or substituted phenyl or R -y is with the proviso that Z is not hydrogen and Z is not "methyl when Y is methyl; and agronomically acceptable salts thereof. • 4
Aryl or R-y is, provided that Z is not w Is hydrogen and Z is not methyl when Y is methyl; and agronomically acceptable salts thereof · Composition according to claim 3, characterized in that 5. A composition according to claim 4, characterized in that U, Y, W, R, R, R ² , R, R ⁴ , G and η have the meaning set out in claim 4, and α is unsubstituted or monosubstituted or disubstituted P is phenyl;
B is monosubstituted or disubstituted phenyl; Y is hydrogen or RQ; and Z is hydrogen, unsubstituted or substituted phenyl or R -W is;
and agronomically acceptable salts thereof «. 6. The composition according to claim 5, characterized in that 7 · Anapruoh composition according to 6, characterized in that jk monosubstituiertea phenyl iat, wherein the Subatitaent Pluor, chlorine, bromine, trifluoromethyl, trifluoromethoxy, Difluormetho- xy or methyl is}
B monosubstituted phenyl, wherein the substituent is Pluor, chlorine, bromine, trifluoromethyl, trifluoromethoxy, difluoromethoxy, carbomethoxy, carboethoxy, Carboiaopropoxy, methylthio or methylsulfonylate; ü is 0; V is hydrogen, such as straight or branched chain, unaubatiertiert or substituted (Cj-Cg) -alkyl, lowerea (C ₁ -Cg) -alkoxy, lower (C ₁ -Cg) -alkylaulfenyl, unaubatituiertea or aubatituiertea Arylaulfenyl, CR, wherein X represents O or S, and R has the meaning as described in Anapruch 6, cyano, lower alkyl (Cj-Cg) alkyl heteroalkyl, wherein the substituent or the alkyl moiety is lower (Cj-C.) Alkoxy, lower (Cj-C ^ -Alkylaulfenyl, unsubstituted or substituted with phenylsulfenyl, lower acyl (Cj-C ^) -carboalkoxy, cyano or lower heteroalkyl; Y is -C- G ; Z y / Aaserstoff, lower (Cj-C,) - alkyl or unsubstituted or substituted phenyl; and G is hydroxy, lower (C 1 -C 3) alkyl, lower (C 1 -C 4) alkoxy, lower (C 1 -C 4) alkylamino, lower alkyl dialkylamino having independently one to four carbon atoms of each alkyl moiety or phenyl. 8. A composition according to claim 7, characterized in that A 4-chlorophenyl, 4-bromophenyl, 4-trifluoromethylphenyl, 4- Trifluoromethoxyphenyl or 4-difluoromethoxyphenyl; B 4-chlorophenyl, 4-bromophenyl, 4-carbomethoxyphenyl, 4-carbomethoxyphenyl, 4-carboisoproposyphenyl, 4-difluoromethoxy phenyl, 4-trifluoromethoxyphenyl, 4-trifluoromethylphenyl, 4-methylthiophenyl or 4-methylsulfonylphenyl 1st; U Oat; V is hydrogen, methyl, methylsulfenyl, 2-NLtrophenylsulfenyl, Garbomethoxy, acetyl, TrLfluoracetyl, formyl or methoxalyl is;
0 Y is -G; G; Z is hydrogen, methyl, phenyl, 4-chlorophenyl, 4-trifluoromethylphenyl, 4-trifluoromethoxyphenyl, 4-trifluorothiomethoxyphenyl, 4-difluoromethoxyphenyl or 4-difluorobromothiomethoxyphenyl G is hydroxy, methyl, ethyl, methoxy, ethoxy, dimethylamines or phenyl; 9 · Composition according to claim 8, characterized in that A is 4-chlorophenyl; B is 4-chlorophenyl; U is 0; V is hydrogen; Y is -C-G; Z is methyl; and G is methoxy. A composition according to claim 8, characterized in that A is 4-chlorophenyl; B is 4-chlorophenyl; U is 0; V is hydrogen; Y is -C-G; Z is methyl; and G is ethoxy. 11. A composition according to claim 8, characterized in that A is 4-chlorophenyl; B is 4-chlorophenyl; U is O; Y is hydrogen; Y is -C-G; Z is methyl; and G Dimethylamine »is · Composition according to Claim 8, characterized in that-A is 4-chlorophenyl; B is 4-chlorophenyl; ü is 0; Y is carbomethoxy; , 0 Y is -C-G; Z is methyl; and G is methoxy. 12 3 4. Y, Z, y, R, R ¹ , R, R ^J , R, G and η have the meaning explained in claim 5 and
A is monosubstituted phenyl;
B is monosubstituted phenyl;
U is 0; and Y -C -gate; and agronomically acceptable salts thereof « 12 3 R, R and R are independently hydrogen, halogen, cyano, nitro, hydroxy, an alkoxy group (OR) of up to four carbon atoms, an amino group (NH ₂ ), an alkylamino group (NHR) of up to six carbon atoms, a dialkylmino group (NR ₂ ) having independently up to six carbon atoms in each alkyl moiety, a carboxy group (CO ₂ H), a carbalkoxy group (CO ₂ R) having up to six carbon atoms, an alkylcarbonyl group (COR) having up to six carbon atoms, an alkanoyloxy group (OCOR) having bis - a ία 8 5 - 237: za six carbon atoms, a carboxamide group (COIHg, CONHR or COUR ₂ ) having independently up to six carbon atoms in each alkyl moiety, a carbamoyloxy group (OCONH ₂ , OCOlTHR or OCQNRg) independently having up to six carbon atoms in each alkyl moiety, a sulfhydryl, a sulfinyl group ( -SOR) having up to six carbon atoms, a sulfonyl group (-SOgR) having up to six carbon atoms, a sulfonate group (-OSOgR) having up to six carbon atoms, an alkylthio group (SR) having up to six carbon atoms, a sulfonamide (SOgMHg, SOgWHR or SOgNRp) having independently up to six carbon atoms in each alkyl moiety, an amido group (NRCOR) independently having up to six carbon atoms in each alkyl moiety, an alkylsulfonamide (NRSOgR) having independently up to six carbon atoms in each alkyl moiety, an alkylthiocarbonyl group (CSR) with bis to six carbon atoms, one thioamide group (NRCSR) with independently up to six Koh in each alkyl moiety, an alkylsulfonamide (NRSOR) having independently up to six carbon atoms in each alkyl moiety, an imido group (1 (COR) COR) having independently up to six carbon atoms in each alkyl moiety, an unsubstituted or substituted straight or branched chain lower (Cj -Cg) -alkyl, (CyCg) -cycloalkyl or aryl, in which the substituent on the alkyl component can be one or more identical or different hydroxy, halogen, cyano, nitro or an alkoxy group (OR) with up to four carbon atoms, an amino group ( NHg), an alkylamino group (NHR) of up to six carbon atoms, a dialkylamino group (NRg) independently having up to six carbon atoms in each alkyl moiety, a carboxy group (COgH), a carbalkoxy group (COgR) of up to six carbon atoms, an alkylcarbonyl group (COR ) having up to six carbon atoms, an alkanoyloxy group (OCOR) having up to six carbon atoms, a Carbosamidgrup pe (CONHg, CONHR or CONRg) having independently up to six carbon atoms in each alkyl moiety, a carbamoyloxy group (OCONHg, OCONHR or OCONRg) having independently up to six carbon atoms in each alkyl moiety, a sulfhydryl, a sulfinyl group (-SOR). - ϊ »7 ώ ** I ö 4 ^) having up to six carbon atoms, a sulfonyl group (-SO ₂ having up to six carbon atoms, a sulfonate group (-OSO ₂ R) having up to six carbon atoms, an alkylthio group (SR) having up to six carbon atoms, a sulfonamide (SO ₂ UH ₂ , SOgHHR or SOgNRg) having independently up to six carbon atoms in each alkyl moiety, an amido group (HRCOR) independently having up to six carbon atoms in each alkyl moiety, an alkylsulfonamide (HRSOgR) having independently up to six carbon atoms in each alkyl moiety, an alkylthiocarbonyl group (CSR) having up to six carbon atoms, a thioamido group (HRCSR) independently having up to six carbon atoms in each alkyl moiety, an alkylsulfonamide (HRSOR) having independently up to six carbon atoms in each alkyl moiety, an imido group (H (COR) COR) having independently up to six Carbon atoms in each alkyl component, or an aryl group, wherein R is an alkyl group with the specified number v on carbon atoms,
> G (C - Cg) -cycloalkyl, unsubstituted or substituted Aryl or R-Q; and η is an integer of 0 to 10; and agronomically acceptable salts thereof; and (2) comprises an agronomically acceptable carrier. A composition according to claim 8, characterized in that *. A is 4-chlorophenyl; B is 4-chlorophenyl; ü is 0; Y is acetyl; Y is -C-G; Z is methyl and G is methoxy. Composition according to Claim 8, characterized in that Ά is 4-chlorophenyl; B is 4-chlorophenyl; U is 0; Y is trifluoroacetyl; Y is -C-G; Z is methyl; and G is methoxy · Composition according to Claim 8, characterized in that A is 4-chlorophenyl; B '4-chlorophenyl is j U is O; V is formyl; Y is -C-G; Z is methyl; and G is methoxy · 16. The composition according to claim 8, characterized in that Δ. 4-chlorophenyl is; B is 4-chlorophenyl; ü is O; V is methoxalyl; Y is -C-G; Z is methyl; and G is methoxy · Composition according to Claim 8, characterized in that α is 4-chlorophenyl; B is 4-bromophenyl; U is 0; V is hydrogen; Y is -C-G; Z is methyl; and G is methoxy · 18. A composition according to claim 8, characterized in that A 4-chlorophenylate; B is 4-trifluoromethylphenyl; ü is 0; V is hydrogen; Y is -C-G; Z is methyl; and G is methoxy. Composition according to Claim 8, characterized in that Α is 4-trifluoromethylphenyl;
B is 4-trifluoromethylphenyl;
UO iat; Y is hydrogen; Υ -GG is;
Z is methyl; and
G methoxyate · 20. The composition according to claim 8, characterized in that A 4-chlorophenyl iat;
Ψ B is 4-trifluoromethoxyphenyl;
U is 0; Y is hydrogen; Y is -C-G; Z is methyl; and
G methoxyate · Composition according to Claim 8, characterized in that A is 4-bromophenyl;
B is 4-trifluoromethylphenyl;
0 iat; , V is hydrogen;
0 Y is -G-G; Z is methyl; and
G methoxy iat. Composition according to Claim 1, characterized in that A, B, U, V, Q, R, R, E, R, R ⁴ and η are as defined in Claim 1 and Y is lower straight or branched chain, unsubstituted or sub-substituted (C ₁ -Cg) alkyl or unsubstituted or substituted aryl; and Z (C, -C ₍ ;) - cycloalkyl, unsubatituted or substituted Composition according to Claim 2, characterized in that V, Y, Z, Y, R, R, R ² , R, R and η are as defined in claim 22 and Ά unsubstituted or substituted phenyl is B unsubstituted or substituted phenyl; and U is 0 or S;
and agronomically acceptable salts thereof. 24. A composition according to claim 23, characterized in that U, Y, Q, R, R ¹ , R ² , R ³ , R ⁴ and η are as defined in claim 23, and α is substituted phenyl; B is substituted phenyl; V is unsubstituted or substituted phenyl or R -Q is; and 25. A composition according to claim 24, characterized in that ü, Y, Z, g, R, R, R ² , R, R and η are as defined in claim 24 J clarified meaning and A is mono-substituted or disubstituted phenyl; B is monosubstituted or disubstituted phenyl; and V is hydrogen or R-Q; and agronomically acceptable salts thereof. 26. A composition according to claim 25 »characterized in that V, Y, Q, R, R, R ² , R ^, R and η have the meaning explained in claim 25 and α is monosubstituted phenyl; B is monosubstituted, phenyl; U is 0; and 27 »Composition according to claim 26, characterized in that A is monosubstituted phenyl wherein the substituent is fluoro, chloro, bromo, trifluoromethyl, trifluoromethoxy, difluoromethoxy or methyl; B is monosubstituted phenyl; wherein the substituent is fluoro, chloro, bromo, trifluoromethyl, trifluoromethoxy, difluoromethoxy, carboroethoxy, carboethoxy, carboisopropoxy, methyl-) thio or methylsulfonyl;
U is 0; Y is hydrogen, lower straight or branched chain, unsubstituted or substituted (C - Cg) alkyl, lower (C ₁ -CG) -alkoxy, lower (Cj-Cg) -ülkylsulfenyl, unsubstitu- _Ψ iertes or substituted arylsulfenyl, 28. A composition according to claim 27, characterized by A 4-chlorophenyl, 4-bromophenyl, 4-trifluoromethylmethyl, 4- Trifluoromethoxyphenyl or 4-difluoromethoxyphenyl iat; B-4-chlorophenyl, 4-bromophenyl, 4-carbomethoxyphenyl, 4-carboxyethoxyphenyl, 4-carboisopropoxyphenyl, 4-difluoromethoxy • "433" phenyl, 4-trifluoromethoxyphenyl, 4-trifluoromethylphenyl, 4-methylthiophenyl or 4-methylsulfonylphenyl; U is O; V is hydrogen, methyl, methyl salfenyl, 2-nitrophenylsulfenyl, carbomethoxy, acetyl, trifluoroacetyl, pormyl or methoxalyl; Y is ethyl, n-propyl, η-butyl, 3-chloropropyl, 4-bromopropyl or phenyl is j and Z is methyl, ethyl, n-propyl, η-butyl or phenyl. 29. A composition according to claim 28, characterized in that A is 4-chlorophenyl; B is 4-chlorophenyl; U is 0; V is hydrogen; Y is phenyl; and Z is methyl. "· 30. A composition according to claim 28, characterized in that A is 4-chlorophenyl; B is 4-chlorophenyl; ü is 0; V is hydrogen; Y is η-butyl; and Z is methyl. 31. The composition according to claim 28, characterized in that A is 4-chlorophenyl; B is 4-chlorophenyl; U is 0; Vaser is; Y is 3-chloropropyl; and Z is methyl. 32. Composition according to one of the preceding claims, characterized in that the compound is present in from about 0.00001 to about 99% mass of the composition. A composition according to claim 32, characterized in that the compound is present in from about 0.00005 to about 90% of the composition.