Herbicidal 4-benzoylisoxazoles are described in a number of patent publications for example European Patent Publication Numbers 0418175, 0487357, 0527036, 0527037, 0560482 and 0560483.

Herbicidal 2-cyano-1,3-diones are described in European Patent Publication Numbers 0213892, 0496630 and 0496631 and International Patent Publication No. WO 95/25099. Herbicidal 5-phenylisoxazoles are described in European Patent Publication Number 0524018.

Herbicidal 4-benzoylpyrazoles are described in European Patent Publication Numbers 0352543 and 0282944 as well as DE 19518054.

However none of the above publications disclose or suggest the presence of an aromatic heterocyclic ring linked by a ring nitrogen atom (optionally via methylene) to the benzoyl ring or the related compounds described and claimed hereinafter.

The present invention provides phenyl derivatives of formula (I): wherein: A represents a group (A-1), (A-2), (A-3) or (A-4):

z represents one or two; when z represents two the XR3 groups may be the same or different; R represents hydrogen or -Co2R4; R1 represents: - lower alkyl or lower haloalkyl; or a cycloalkyl group containing from three to six carbon atoms optionally substituted by one or more R12 groups or one or more halogen atoms; Ra represents lower alkyl, lower haloalkyl, lower alkenyl or lower alkynyl; Rb represents hydrogen, lower alkyl, lower haloalkyl, lower alkoxy, halogen, -S(O)xR4, -C02R4, -CH2OR4, -CH2SR4 or cyclopropyl; x represents zero, one or two; R2 represents:- halogen; lower alkyl which is substituted by one or more groups -OR5; a cycloalkyl group containing from three to six carbon atoms; or a group selected from nitro, cyano, -CO2R5, -NR5R6, -S(o)pR7, -O(CH2)mORS, -COR5, -N(R8)S02R7, -OR7, -OH, -OSO2R7, -(CR9R1 O)tS(O)qR7, -CONR5R6, -N(R8)-C(Z)=Y, -C(R9R10)NR8R1 1, -CH2P(=O)RSaRSb, R12 SF5 and benzyl optionally substituted by from one to five groups R13 which may be the same or different; or two groups R2, together with adjacent carbon atoms of the phenyl ring form a second phenyl ring or a 5- or 6-membered saturated or unsaturated heterocyclic ring which is fused to the first ring and contains one or two oxygen or sulphur atoms and is optionally substituted by one or more halogen, lower alkyl, lower haloalkyl or lower alkoxy groups, or one of the ring carbon atoms of the heterocyclic ring forms part of a carbonyl group or an oxime or lower alkoxyimine derivative thereof; (examples of the optionally substituted fused ring systems when formed include thiochroman, chroman, 2H-thiochromene, 2H-chromene, 4H-thiochromene, 4H-chromene, isothiochroman, isochroman, isothiochromene, isochromene, 1,3-benzodithiole, 1,3-

benzodioxole, 1,3-benzoxathiole, 1,4-benzodithiin, 1,4-benzoxathiin, 1,4-benzoxathian, 1,3-benzoxathian, 3,1 -benzoxathian and 1,3- benzodithian); n represents zero or an integer from one to three; where n is greater than one the groups R2 may be the same or different; m represents one, two or three; p and q represent zero, one or two; t represents one, two, three or four (preferably one); when t is more than one, R9 and R10 may be the same or different; R3 represents a 5-membered heteroaromatic ring of formula (II): in which D, E, G and J independently represent CRl4 or a nitrogen atom, with at least one of D, E, G and J representing CR14 (when more than one CR14 group is present they may be the same or different); or two adjacent groups CR14 may form a phenyl or 5- to 7- membered heteroaromatic ring which is fused to the first ring and is optionally substituted by one or more groups Rl 5; and when present the 5- to 7- membered heterocyclic ring contains from one to four heteroatoms in the ring which may be the same or different selected from nitrogen, oxygen and sulphur; X represents -(CR9R10)v-; R4 represents:- lower alkyl or lower haloalkyl; R5 and R6 which may be the same of different, each represents hydrogen or R12; R5a and R5b which may be the same of different, each represents lower alkyl or lower alkoxy; R7 represents:- R12; or a cycloalkyl group containing from three to six carbon atoms; or a group -(CH2)w-[phenyl optionally substituted by from one to five groups R13 which may be the same or different]; w represents zero or one;

R8 represents:- hydrogen, R7, or OR1 6; R9 and R10 independently represent hydrogen, lower alkyl or lower haloalkyl (preferably containing up to three carbon atoms); R11 represents -So2R7 or R12 represents:- lower alkyl, lower haloalkyl, lower alkenyl, lower haloalkenyl, lower alkynyl or lower haloalkynyl; R13 represents a group selected halogen, R17 nitro, cyano, -Co2R5, -S(O)pR 16, -OR16 and -NR5R6; R14 represents:- a group selected from hydrogen, halogen, R17, nitro, cyano, -Co2R5, -S(O)pRl6, -ORl6, -NR5R6 and cyclopropyl; R15 represents halogen, or R12; R16 represents lower alkyl or lower haloalkyl; R17 represents a straight- or branched- chain alkyl group containing one to three carbon atoms optionally substituted by one or more halogen atoms; Y is oxygen or sulphur (preferably Y represents oxygen); Z represents a group selected from R12, -NR18R19, -SR7 and -OR7; R18 and R19 independently represent hydrogen or R7; Q represents hydrogen, lower alkyl, lower haloalkyl, lower alkenyl, lower haloalkenyl, lower alkynyl, lower haloalkynyl, -CH2CN, -So2R4, -SO2R20, -(CSH2S)C(O)R112, -(CUH2u)C(O)R20, -CH20CO2R12, -CH2NHC(O)R1 2, -CH2NHCO2R1 2, -COCH20C(O)Rl 6, -COCH2OR12, -COCH20R20, -CONR5R6, -CONR20R21, -CONR22R23, -CO2R12, -CO2R20, -P(O)R5aR5b and lower alkyl substituted by a group selected from -CONR9R1 0, OR9, -NR5R6, -CO2R9, R20 and -S(O)pRl2; R20 represents phenyl optionally substituted by one to five groups selected from halogen, lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, nitro, cyano, -S(o)pR7 and -NR5R6; R21 represents R5 or R20;

R22 and R23 together with the adjacent nitrogen atom represent a piperidine, pyrrolidine, piperazine or morpholine ring; s and u represent zero or one to six; and wherein v represents the value zero when A represents a formula (A-l), (A-2) or (A-3); or when A represents a formula (A-4), v represents the value zero or one; and agriculturally acceptable salts and metal complexes thereof; which possess valuable herbicidal properties.

In the description unless otherwise specified the following terms are generally defined thus:- 'lower alkyl' means a straight- or branched- chain alkyl group having one to six carbon atoms; 'lower haloalkyl1 means a straight- or branched- chain alkyl group having one to six carbon atoms, substituted by one or more halogens; 'lower alkoxy' means a straight- or branched- chain alkoxy group having one to six carbon atoms; 'lower haloalkoxy' means a straight- or branched- chain alkoxy group having one to six carbon atoms, substituted by one or more halogens; 'lower alkenyl' means a straight- or branched- chain alkenyl group having two to six carbon atoms; 'lower haloalkenyl' means a straight- or branched- chain alkenyl group having two to six carbon atoms, substituted by one or more halogens; 'lower alkynyl' means a straight- or branched- chain alkynyl group having three to six carbon atoms; 'lower haloalkynyl' means a straight- or branched- chain alkynyl group having three to six carbon atoms, substituted by one or more halogens; 'halogen' means a fluorine, chlorine, bromine or iodine atom.

By the term "agriculturally acceptable salts" is meant salts the cations or anions of which are known and accepted in the art for the formation of salts for agricultural or horticultural use. Preferably the salts are water-soluble. Suitable salts with bases include alkali metal (eg. sodium and potassium), alkaline earth metal (eg. calcium and magnesium), ammonium and amine (eg. diethanolamine,

triethanolamine, octylamine, morpholine and dioctylmethylamine) salts.

Suitable acid addition salts, formed by compounds of formula (I) containing an amino group, include salts with inorganic acids, for example hydrochlorides, sulphates, phosphates and nitrates and salts with organic acids, for example acetic acid.

Furthermore in certain cases the substituents R and R1 to R23 may contribute to optical isomerism and/or stereoisomerism. All such forms are embraced by the present invention.

The compounds of the invention, in certain aspects of their properties, for example their control of weeds found in maize and soya such as Abutilon theoohrasti, or in rice for example Echinochloa orvzicola and Lindernia procumbens, show advantageous properties over known compounds.

The present invention includes 4-benzoylisoxazole derivatives of formula (Ia): wherein X represents -(CR9Rl0)v- and v represents zero.

The present invention includes 5-phenylisoxazole derivatives of formula (Ib): wherein X represents -(CR9Rl0)v- and v represents zero.

The present invention includes 2-cyano-1,3-dione derivatives of formula (Ic):

wherein X represents -(CR9Rl0)v- and v represents zero.

Compounds of formula (Ic) may exist in enolic tautomeric forms that may give rise to geometric isomers around the enolic double bond.

By the term "metal complexes" is meant compounds in which one or both of the oxygen atoms of the 1,3-dione of formula (Ic) act as chelating agents to a metal cation. Examples of such cations include zinc, manganese, cupric, cuprous, ferric, ferrous, titanium and aluminium.

The present invention also includes 4-benzoylpyrazole derivatives of formula (Id): wherein X represents -(CR Rl0)v- and v represents zero or one.

In the description that follows, reference to compounds of formula (I) means reference to a compound of formula (Ia), (Ib), (Ic) or (Id).

Compounds of formula (Ia) above are preferred.

Compounds in which one XR3 group is present are preferred (preferably the XR3 group is at the 2- or 4- position on phenyl).

Compounds in which the 2- and 4-positions of phenyl are substituted are also preferred.

Compounds wherein X represents -(CH2)V- are preferred.

Compounds in which v represents zero are especially preferred.

Preferably R3 is selected from pyrazol-l-yl, imidazol-1-yl, 1 ,2,4-triazol- 1 -yl, 1 ,2,3-triazol- 1 -yl, 1,2,3-triazol-2-yl and

1,2,3 ,4-tetrazol- 1 -yl (1,2,3 -triazol- 1 -yl and 1,2,3-triazol-2-yl are more preferred, and 1,2,4-triazol-l-yl is most preferred).

Preferably R3 is a ring of formula (II) wherein R14 represents hydrogen, halogen or R1 7.

In formula (I) above, preferably the 5- and 6- positions of phenyl are unsubstituted.

Preferably R represents hydrogen or CO2R4 wherein R4 represents a straight- or branched- chain alkyl group containing up to three carbon atoms.

Preferably R1 represents cyclopropyl or l-methylcyclopropyl (cyclopropyl is especially preferred).

Preferably R2 represents halogen, a straight- or branched- chain alkyl group containing up to four carbon atoms optionally substituted by one or more halogen atoms; a group selected from nitro, cyano, -S(O)pR7 -OR7 and -CH2S(O)qR7 wherein R7 represents lower alkyl or lower haloalkyl; or benzyl optionally substituted by -S(O) pRl6 wherein R16 represents lower alkyl; or two groups R2 together with adjacent carbon atoms of the phenyl ring form a second phenyl ring.

Preferably n represents one or two.

Compounds of formula (Id) wherein Q represents -SO2R20, CH2COR20 or CH2R20 are preferred.

Compounds of formula (Id) wherein Ra represents methyl or ethyl are preferred.

Compounds of formula (Id) wherein Rb represents hydrogen, C1 -3 alkyl, haloalkyl or cyclopropyl are preferred (methyl is especially preferred).

A preferred class of compounds of formula (Ia) above are those wherein: - R represents hydrogen or -Co2R4; R1 represents cyclopropyl or 1-methylcyclopropyl; R2 represents:- a straight- or branched- chain alkyl group containing up to four carbon atoms optionally substituted by one or more halogen atoms; or

a group selected from halogen, nitro, -S(o)pR7, -oR7, -CH2S(O)qR7> -CH2NR8R1 1, -N(R8)So2R7, -N(R8)Co2R7, -CH2P(O)R5aR5b and benzyl optionally substituted by -S(O)pRl 6; or two groups R2 together with adjacent carbon atoms of the phenyl ring form a second phenyl ring; n represents zero, one or two; R3 represents a 5-membered heteroaromatic ring of formula (II) which is selected from pyrazol-l-yl, imidazol-l-yl, 1,2,4-triazol-l-yl, 1,2,3,-triazol-1-yl, 1,2,3-triazol-2-yl, 1,2,3,4-tetrazol-1-yl, indazol-1-yl, benzotriazol-l-yl, benzimidazol-l-yl and indol-l-yl, which are substituted by one or two groups R14 (and wherein one or two R3 groups are present); R4 represents methyl or ethyl; R7 and R8 independently represent lower alkyl or lower haloalkyl; R11 represents -So2R7 or C02R7; K14 represents hydrogen, halogen, a straight- or branched- chain alkyl group containing up to three carbon atoms optionally substituted by one or more halogen atoms; or -S(O)pRl6, NO2 or CO2R5 wherein R5 represents lower alkyl; and R16 represents lower alkyl.

A particularly preferred class of compounds of formula (Ia) above are those wherein:- R represents hydrogen or -Co2R4 wherein R4 represents ethyl; R1 represents cyclopropyl; R2 represents:- halogen; a straight- or branched- chain alkyl group containing up to four carbon atoms optionally substituted by one or more halogen atoms; or a group selected from -S(o)pR7, ~CH2S(O)qR7 -OR7 and benzyl optionally substituted by -S(O)pRl6; or two groups R2 together with adjacent carbon atoms of the phenyl ring form a second phenyl ring; or two groups R2 together with adjacent carbon atoms form a 1,4- benzoxathian ring; R3 represents a pyrazol-1-yl, imidazol-1-yl, 1,2,3-triazol-1-yl, 1,2,3 -triazol-2-yl, 1 ,2,4-triazol- 1 -yl, 1,2,3,4-tetrazol-1 -yl or benz-1,2,3-

triazol-1-yl ring substituted by one or two R14 groups, wherein R14 represents hydrogen, optionally halogenated methyl or -S(O)pRl6; R7 and K16 represent methyl or ethyl; and n represents 0, 1 or 2.

A further particularly preferred class of compounds of formula (Ia) above are those wherein:- R represents hydrogen or -C02R4 wherein R4 represents ethyl; R1 represents cyclopropyl; R2 represents:- halogen; a straight- or branched- chain alkyl group containing up to four carbon atoms optionally substituted by one or more halogen atoms; or a group selected from -S(o)pR7, CH2S(O)qR7, -OR7 and benzyl optionally substituted by -S(O)pRl 6; or two groups R2 together with adjacent carbon atoms of the phenyl ring form a second phenyl ring; R3 represents a pyrazol-l-yl, imidazol-l-yl, 1 ,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, 1,2,4-triazol-l-yl or 1,2,3 ,4-tetrazol- 1 -yl ring substituted by one or two R14 groups, wherein R14 represents hydrogen, optionally halogenated methyl or -S(O)pR16; R7 and R16 represent methyl or ethyl; and n represents 0, 1 or 2.

A further particularly preferred class of compounds of formula (Ia) above are those wherein:- R represents hydrogen or -C02R4 wherein R4 represents ethyl; R1 represents cyclopropyl; R2 represents:- halogen, optionally halogenated methyl, -S(O)pCH3, OCH3 or benzyl optionally substituted by -S(O)pCH3; R3 represents imidazol-l-yl, 1,2,3 -triazol- 1 -yl, 1,2,3-triazol-2-yl or 1,2,4-triazol-l-yl, optionally substituted on the ring carbon atoms by one or two methyl groups; and n represents one or two.

A most preferred class of compounds of formula (Ia) above are those wherein:- R represents hydrogen or -Co2R4 wherein R4 represents ethyl;

R1 represents cyclopropyl; R2 represents 2-CF3 and R3 represents 4-(1,2,3-triazol-1-yl), 4- (1,2,3-triazol-2-yl) or 4-(1,2,4-triazol-1-yl); or R2 represents 4-CF3 and R3 represents 2-(1,2,3-triazol-1-yl), 2- (1,2,3-triazol-2-yl) or 2-(1,2,4-triazol-1-yl).

A preferred class of compounds of formula (Id) above are those wherein:- Ra represents methyl or ethyl; Q represents a group selected from hydrogen, lower alkyl, lower alkenyl, lower alkynyl, -So2R4, -S02R20, -(CSH2S)C(O)r12, and -(CUH2u)C(o)R20; or methyl or ethyl substituted by CO2R9 or R20; s and u represent zero or one; R2 represents:- a straight- or branched- chain alkyl group containing up to three carbon atoms optionally substituted by one or more halogen atoms; or a group selected from halogen, nitro, -S(O)pR12, -OR12, -CH2S(O)qR12, -CH2NK8K1 1, -N(R8)SO2R12, and -N(R8)CO2R12; or benzyl optionally substituted by -S(O)pR16; n represents zero, one or two; X represents -(CH2)v-; R3 represents a 5-membered heteroaromatic ring of formula (II) which is selected from pyrazol-l-yl, imidazol-l-yl, 1,2,4-triazol-1-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, 1,2,3,4-tetrazol-1-yl and benzimidazol-1-yl, the ring systems of which are substituted by one or two R14 groups; z represents one; Rb represents hydrogen or methyl; R8, R9 and R12 independently represent C14 alkyl or haloalkyl; R11 represents -SO2R12 or C02R12; R16 represents C14 alkyl; and R17 represents phenyl optionally substituted by C 1-3 alkyl.

A particularly preferred class of compounds of formula (Id) above are those wherein:- Ra represents methyl;

Q represents a group selected from hydrogen, C14 alkyl, C2-4 alkenyl, C34 alkynyl, -So2R4, -SO2R20, -(CSH2S)C(O)R12, and -(CUH2u)C(O)R20; or methyl or ethyl substituted by a group selected from CO2K9 and R20; s and u represent zero or one; R2 represents:- a straight- or branched- chain alkyl group containing up to three carbon atoms optionally substituted by one or more halogen atoms; or a group selected from halogen, nitro, S(O)pR12 -OR12 and -CH2S(O)qR12; or benzyl optionally substituted by -S(O)pR16; n represents one; X represents a bond; R3 is selected from pyrazol-l-yl, imidazol-l-yl, 1,2,4-triazol-1-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl and 1,2,3,4-tetrazol-1-yl, the ring systems of which are substituted by one or two R14 groups; z represents one; Rb represents hydrogen or methyl; R9, R12 R14 and R16 represent C14 alkyl; and R20 represents phenyl optionally substituted by methyl.

A further particularly preferred class of compounds of formula (Id) above are those wherein:- Ra represents methyl; Rb represents hydrogen or methyl; Q represents a group selected from hydrogen, C 1 4 alkyl, C24 alkenyl, C34 alkynyl, -So2R4, -SO2R20, -(CH2)5C(O)R12, and -(CH2)uC(O)R20; or methyl or ethyl substituted by a group selected from C02R9 and R20; s and u represent zero or one; R2 represents:- a straight- or branched- chain alkyl group containing up to three carbon atoms optionally substituted by one or more halogen atoms; n represents one; X represents a bond; R3 represents a 1,2,4-triazol-1-yl ring;

z represents one; R9 and R12 represent C14 alkyl; and R20 represents phenyl optionally substituted by methyl.

A further particularly preferred class of compounds of formula (Id) above are those wherein:- Ra represents methyl; Rb represents hydrogen or methyl; Q represents a group selected from hydrogen, C 1-4 alkyl, C24 alkenyl, C34 alkynyl, -So2R4, -SO2R20, -C(O)R12, and -(CH2)UC(O)R20; or -CH2R20; u represents zero or one; R2 represents:- halogen or a straight- or branched- chain alkyl group containing up to three carbon atoms substituted by one or more halogen atoms; n and z represent one; X represents a bond; R3 represents a 1,2,4-triazol-1-yl ring; R12 and R16 represent C14 alkyl; and R20 represents phenyl optionally substituted by methyl.

A further particularly preferred class of compounds of formula (Id) above are those wherein:- Ra represents methyl; Rb represents hydrogen or methyl; R2 represents:- optionally halogenated methyl; n represents one; Q represents -SO2R20, CH2COR20 or CH2R20; X represents a bond; R3 represents a 1,2,4-triazol-1-yl ring; z represents one; and R20 represents phenyl optionally substituted by methyl.

Particularly important compounds of the invention include: ethyl 5 -cyclopropyl4- [4-(1,2,4-triazol-1 -yl)-2- trifluoromethylbenzoyl]isoxazole-3-carboxylate (Compound 1)

ethyl 5-cyclopropyl4-[4-(3-methylthio- 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]isoxazole-3-carboxylate (Compound 2) ethyl 5-cyclopropyl-4- [4-(1,2,4-triazol- 1 -yl)naphth-1- oyl]isoxazole-3-carboxylate (Compound 3) ethyl 5-cyclopropyl-4-[2-chloro4-(1 ,2,4-triazol-1- yl)benzoyl]isoxazole-3-carboxylate (Compound 4), ethyl 5-cyclopropyl-4- [2-iodo4-( 1 ,2,4-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 5) ethyl 5-cyclopropyl-4-[2-methyl4-( 1 ,2,4-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 6) ethyl 5-cyclopropyl-4-[2-benzyl-4-(1,2,4-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 7) ethyl 5-cyclopropyl-4-[4-(imidazol- I -yl)-2- trifluoromethylbenzoyl]isoxazole-3-carboxylate (Compound 8) ethyl 5-cyclopropyl-4-[4-(imidazol- 1 -yl)naphth- 1 -oyl]isoxazole-3 - carboxylate (Compound 9) ethyl 5-cyclopropyl4-[2-chloro-4-(imidazol- I - yl)benzoyl]isoxazole-3-carboxylate (Compound 10) ethyl 5-cyclopropyl-4-[4-(imidazol-1-yl)-2- iodobenzoyl]isoxazole-3-carboxylate (Compound 11) ethyl 5-cyclopropyl-4-[4-(pyrazol- 1-yl)-2- trifluoromethylbenzoyl]isoxazole-3-carboxylate (Compound 12) ethyl 5-cyclopropyl-4- [2-chloro-4-(pyrazol- 1- yl)benzoyl]isoxazole-3-carboxylate (Compound 13) 5-cyclopropyl4-[4-( 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]isoxazole (Compound 14) 5-cyclopropyl-4-[2-(1,2,4-triazol- 1 -yl)benzoyl]isoxazole (Compound 15) 5-cyclopropyl-4-[2-(pyrazol-1-yl)benzoyl]isoxazole (Compound 16) ethyl 5-cyclopropyl-4-[2-( 1 ,2,4-triazol- 1 -yl)benzoyl]isoxazole-3 - carboxylate (Compound 17) ethyl 5-cyclopropyl-4-[2-(1,2,4-triazol-1-yl)-4- trifluoromethylbenzoyl]isoxazole-3-carboxylate (Compound 18) ethyl 5-cyclopropyl-4- [4-(3 -methylsulphinyl- 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]isoxazole-3-carboxylate (Compound 19)

ethyl 5 -cyclopropyl-4- [4-(3 -methylsulfonyl- 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]isoxazole-3-carboxylate(Compound 20) ethyl 5-cyclopropyl-4- [2,3 -bis-(methylthio)-4-( 1 ,2,4-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 21) ethyl 5-cyclopropyl4-[2,3-bis-(methylthio)4-(imidazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 22) ethyl 5-cyclopropyl-4-[3 -fluoro-2-methylthio-4-( 1 ,2,4-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 23) ethyl 5-cyclopropyl-4- [2-methylthio-3 ,4-bi s-( 1 ,2,4-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 24) ethyl 5-cyclopropyl-4-[3 -bromo-2-methylthio4-( 1 ,2,4-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 25) ethyl 5-cyclopropyl-4- [2-methylthio4-( 1 ,2,4-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 26) ethyl S-cyclopropyl-4- [2-methylthio4-(imidazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 27) ethyl 5-cyclopropyl-4- [2-ethyl-3 -methylthio4-( 1 ,2,4-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 28) ethyl 5-cyclopropyl-4- [2-isobutyl4-( 1 ,2,4-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 29) ethyl 5-cyclopropyl-4- [2-isobutyl-4-(imidazol- 1 yl)benzoyl]isoxazole-3-carboxylate (Compound 30) ethyl 5-cyclopropyl-4-[3-methoxy-2-methylthio-4-(1,2,4-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 31) ethyl 5 -cyclopropyl-4- [2,3 -bis-(methylthio)4-( 1,2,3 -triazol-2- yl)benzoyl]isoxazole-3-carboxylate (Compound 32) ethyl 5 -cyclopropyl-4- [3 -bromo-2 -methylthio4-(1,2,3 -triazol-2- yl)benzoyl]isoxazole-3-carboxylate (Compound 33) ethyl 5-cyclopropyl-4-[3 -bromo-2-methylthio-4-(1,2,3 -triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 34) ethyl 5-cyclopropyl-4-[2-methylthio-4-( 1,2,3-triazol-2- yl)benzoyl]isoxazole-3-carboxylate (Compound 35) ethyl 5-cyclopropyl-4- [2,3 -bis-(methylthio)-4-(3 -methyl- 1,2,4- triazol-l-yl)benzoyl]isoxazole-3-carboxylate (Compound 36) ethyl 5-cyclopropyl-4-[3-bromo-2-methylthio-4-(3-methyl-1,2,4- triazol-1-yl)benzoyl]isoxazole-3-carboxylate (Compound 37)

ethyl 5-cyclopropyl-4-[3-bromo-2-methylthio-4-(5-methyl-1,2,4- triazol4-yl)benzoyl]isoxazole-3 -carboxylate (Compound 38) ethyl 5 -cyclopropyl-4- [2-methylthiomethyl-4-(1,2,4-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 39) ethyl 5-cyclopropyl-4-[2,3-bis-(methylthio)-4-(tetrazol-1- yl)benzoyl]isoxazole-3-carboxylate (Compound 40) ethyl 5-cyclopropyl-4-[2-methylthio-4-(tetrazol-1- yl)benzoyl]isoxazole-3-carboxylate (Compound 41) ethyl 5-cyclopropyl-4-[2-ethyl-3 -methylthio-4-(tetrazol- 1- yl)benzoyl]isoxazole-3-carboxylate (Compound 42) ethyl 5 -cyclopropyl4- [2-ethyl-3 -methylthio4-(1,2,3 -triazol-2- yl)benzoyl]isoxazole-3-carboxylate (Compound 43) ethyl 5-cyclopropyl-4-[2-ethyl-3-methylthio-4-(1,2,3-triazol- 1 - yl)benzoyl]isoxazole-3 -carboxylate (Compound 44) ethyl 5-cyclopropyl-4- [2-isobutyl-4-(1,2, ,2,3-triazol-1- yl)benzoyl]isoxazole-3-carboxylate (Compound 45) ethyl 5-cyclopropyl-4-[2-methylthio-4-(3 methyl 2,4-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 46) ethyl 5-cyclopropyl-4-[2-ethyl-3-methylthio-4-(3-methyl-1,2,4- triazol-1-yl)benzoyl]isoxazole-3-carboxylate (Compound 47) ethyl 5-cyclopropyl-4-[2-isobutyl-4-(3-methyl- 1,2,4-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 48) 2-cyano-3-cyclopropyl- 1 -[4-(1 ,2,4-triazol- 1 -yl)-2- trifluoromethylphenyl]propan- 1,3-dione (Compound 49) 5-cyclopropyl4-[2-methylthio-4-( 1 ,2,4-triazol- 1 - yl)benzoyl]isoxazole (Compound 51) 5-cyclopropyl-4-[2-methyl-4-(1,2,4-triazol-1-yl)- benzoyl]isoxazole (Compound 56) 5-cyclopropyl-4-[2-methylsulfinyl-4-(1,2,4-triazol- 1 - yl)benzoyl]isoxazole (Compound 91) 5-cyclopropyl-4-[2-methylsulfonyl-4-(1,2,4-triazol- 1 - yl)benzoyl]isoxazole (Compound 92) ethyl 5-cyclopropyl-4-[3-fluoro-2-methylthio4-(imidazoi- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 116) ethyl 5-cyclopropyl-4-[2-methyl-4-(1,2,3,4-tetrazol-1- yl)benzoyl]isoxazole-3-carboxylate (Compound 129)

ethyl 5-cyclopropyl-4- [2-chloro-4-(1,2,3 ,4-tetrazol-l- yl)benzoyl]isoxazole-3-carboxylate (Compound 132) ethyl 5 -cyclopropyl-4- [2-trifluoromethyl-4-(1,2,3 -triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 154) ethyl 5-cyclopropyl4-[2-methylthio-4-( 1 ,2,3-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 155) ethyl 5-cyclopropyl4-[2-methyl4-(1,2,3-triazol-1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 158) ethyl 5-cyclopropyl-4- [2-chloro-4-(1,2,3 -triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 160) ethyl 5-cyclopropyl-4- [2-trifluoromethyl-4-( 1,2,3 -triazol-2- yl)benzoyl]isoxazole-3-carboxylate (Compound 167) ethyl 5-cyclopropyl-4-[2-chloro-4-(1,2,3-triazol-2- yl)benzoyl]isoxazole-3-carboxylate (Compound 173) ethyl 5-cyclopropyl-4-[2-methylthio-4-(1,2,3-benztriazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 184) 5-cyclopropyl-4-[2-( 1 ,2,4-triazol- 1 -yl)-4- trifluoromethylbenzoyl]isoxazole (Compound 246) ethyl 5-cyclopropyl-4-[2-(1 ,2,3 ,4-tetrazol- 1 -yl)-4- trifluoromethylbenzoyl]isoxazole-3 -carboxylate (Compound 291) ethyl 5-cyclopropyl-4-[2-( 1,2,3 -triazol- 1 -yl)-4- trifluoromethylbenzoyl]isoxazole-3-carboxylate (Compound 311) ethyl 5-cyclopropyl-4-[2-(1,2,3-triazol-2-yl)-4- trifluoromethylbenzoyl]isoxazole-3-carboxylate (Compound 321) 2-cyano-3-cyclopropyl- 1 -[2-( 1 ,2,4-triazol- 1 -yl)-4- trifluoromethylphenyl]propan-1,3-dione (Compound 424) 5-cyclopropyl-4- [8-( 1 ,2,4-triazol- 1 -yl)- 1 ,4-benzoxathian-5 - oyl]isoxazole (Compound 428) ethyl 5-cyclopropyl-4- [8-( 1,2,3 ,4-tetrazol- 1 -yl)- 1 ,4-benzoxathian- 5-oyl]isoxazole-3-carboxylate (Compound 429) ethyl 5-cyclopropyl-4-[8-( 1 ,2,3-triazol-2-yl)- 1,4-benzoxathian-5- oyl]isoxazole-3-carboxylate (Compound 430) ethyl 5-cyclopropyl4-[3-methoxy-2-methylthio4-( 1 ,2,3-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 431) ethyl 5-cyclopropyl4-[8-( 1,2,3 -benztriazol- 1 -yl)- 1,4- benzoxathian-5-oyl]isoxazole-3-carboxylate (Compound 432)

ethyl 5-cyclopropyl4- [3-methoxy-2-methylthio4-(imidazol 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 433) ethyl 5-cyclopropyl-4-[2-isobutyl-4-(5-methyl-1,2,4-triazol-1- yl)benzoyl]isoxazole-3-carboxylate (Compound 434) I ,3 -dimethyl-5 -hydroxy-4-[4-(1,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl] - 1 H-pyrazole (Compound 501) 1 ,3-dimethyl-5-phenacyloxy-4- [4-( 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]-1H-pyrazole (Compound 502) 1,3-dimethyl-5-methoxy-4-[4-(1,2,4-triazol-1-yl)-2- trifluoromethylbenzoy1]- 1H-pyrazoie (Compound 503) 5 -ethoxy- 1,3 -dimethyl-4- ,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoy1]- 1H-pyrazole (Compound 504) 1 ,3-dimethyl-5-isopropyloxy-4- [4-( 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl] - 1 H-pyrazole (Compound 505) 5-benzyloxy- 1,3 -dimethyl-4-[4-(1,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoy1]- 1H-pyrazole (Compound 506) 1,3-dimethyl-5-methoxycarbonylmethoxy-4-[4-(1,2,4-triazol-1- yl)-2-trifluoromethylbenzoyl]- 1 H-pyrazole (Compound 507) 1,3-dimethyl-5-[1-(methoxycarbonyl)ethoxy]-4-[4-(1,2,4-triaz ol- 1 -yl)-2-trifluoromethylbenzoyl]- 1 H-pyrazole (Compound 508) 1,3-dimethyl-5-allyloxy-4-[4-(1,2,4-triazol-1-yl)-2- trifluoromethylbenzoy1]- 1H-pyrazole (Compound 509) 1,3 -dimethyl-5-propargyloxy4- [4-( 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]-1 H-pyrazole (Compound 510) 5 -benzenesulfonyloxy- 1,3-dimethyl-4-[4-(1,2,4-triazol-1 -yl)-2- trifluoromethylbenzoy1]- 1H-pyrazole (Compound 511) 5-acetyloxy- 1,3 -dimethyl4- [4-( 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]-1H-pyrazole (Compound 512) 5-benzoyloxy-1,3-dimethyl-4-[4-(1,2,4-triazol-1-yl)-2- trifluoromethylbenzoyl]-1H-pyrazole (Compound 513) 1,3 -dimethyl-5-pivaloyloxy-4- [4-( 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]-1H-pyrazole (Compound 514) 1,3 -dimethyl-5 -p-toluenesulfonyloxy-4- [4-( 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]-1H-pyrazole (Compound 515) 1,3-dimethyl-5-isopropylsulfonyloxy-4-[4-(1,2,4-triazol-1-yl )-2- trifluoromethylbenzoy1]- 1H-pyrazoie (Compound 516)

5-hydroxy- 1 -methyl-4-[4-(1,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]- 1 H-pyrazole (Compound 517) 1,3-dimethyl-5-p-toluenesulfonyloxy-4-[4-(1,2,4-triazol-1-yl )-2- chlorobenzoyl]- 1 H-pyrazole (Compound 546) 1,3-dimethyl-5-hydroxy-4-[4-(1,2,4-triazol-1-yl)-2- chlorobenzoyl]-1H-pyrazole (Compound 1116) 1-methyl-5-benzoyloxy-4-[4-(1,2,4-triazol-1-yl)-2- trifluoromethylbenzoyl]-1H-pyrazole (Compound 1117) 1-methyl-5-pivaloyloxy-4-[4-(1,2,4-triazol-1-yl)-2- trifluoroemthylbenzoyl]-1H-pyrazole (Compound 1118) 1 -methyl-5-benzenesulfonyloxy-4- [4-( 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]- 1 H-pyrazole (Compound 1119) 1-methyl-5-p-toluenesulfonyloxy-4-[4-(1,2,4-triazol-1-yl)-2- trifluoromethylbenzoyl]-1H-pyrazole (Compound 1120) 1,3-dimethyl-5-acetoxy-4-[2-chloro-4-(1,2,4-triazol-1-yl)ben zoyl]- 1H-pyrazole (Compound 1121) 1,3 -dimethyl-5 -pivaloyloxy-4- [2-chloro-4-( 1 ,2,4-triazol- 1 - yl)benzoyl]- 1 H-pyrazole (Compound 1122) 1,3-dimethyl-5-benzenesulfonyloxy-4-[2-chloro-4-(1,2,4-triaz ol-1- yl)benzoyl]-lH-pyrazole (Compound 1123) 1,3-dimethyl-5-isopropylsulfonyloxy-4-[2-chloro-4-(1,2,4-tri azol- 1 -yl)benzoyl]- 1 H-pyrazole(Compound 1124) 1,3 -dimethyl-5-methoxy-4- [2-chloro-4-( 1 ,2,4-triazol- 1 - yl)benzoyl]-lH-pyrazole (Compound 1125) 1,3 -dimethyl-5-phenacyloxy-4-[2-chloro-4-(1,2,4-triazol- 1 - yl)benzoyl]-lH-pyrazole (Compound 1126) 1,3-dimethyl-5-benzyloxy-4-[2-chloro-4-(1,2,4-triazol-1- yl)benzoyl]-lH-pyrazole (Compound 1127) 1,3 -dimethyl-5-propargyloxy4-[2-chloro4-( 1 ,2,4-triazol- 1- yl)benzoyl]-lH-pyrazole (Compound 1128) 1,3-dimethyl-5-allyloxy-4-[2-chloro-4-(1,2,4-triazol-1- yl)benzoyl]-lH-pyrazole (Compound 1129) 1 -methyl-5-acetoxy-4-[4-(1,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]-1H-pyrazole (Compound 1130) 1-methyl-5-benzyloxy-4-[4-(1,2,4-triazol-1-yl)-2- trifluoromethylbenzoyl]-1H-pyrazole (Compound 1131) and

1-methyl-5-allyloxy-4-[4-(1,2,4-triazol-1-yl)-2- trifluoromethylbenzoyl]- 1 H-pyrazole (Compound 1132).

The following compounds of formula (Ia) in which R1 represents cyclopropyl and the group (XR3)z is attached either to the 4-position of the phenyl ring (Table 1), or to the 2-position of the phenyl ring (Table 2), or to the 3-position of the phenyl ring (Table 3) form part of the present invention. Note that in the Tables that follow, Me means methyl, Et means ethyl, Pr means propyl, cPr means cyclopropyl, Bu means butyl, and Ph means phenyl. Where subscripts do not appear in the Table it will be understood that in appropriate cases they are present (e.g. CF3 means CF3 etc.). Where a second XR3 group is present in the phenyl ring, its locant is shown in the Tables under the (XR3)z column.

TABLE 1 Cpd R (R2)n (XR3)z No. 1 CO2Et 2-CF3 1,2,4-triazol- 1 -yl 2 CO2Et 2-CF3 3 -SMe- 1,2,4-triazol- 1 -yl 4 CO2Et 2-C1 1 ,2,4-triazol- 1 -yl 5 CO2Et 2-I 1,2,4-triazol-1-yl 6 CO2Et 2-Me 1,2,4-triazol-1-yl 7 CO2Et 2-CH2Ph 1,2,4-triazol-1-yl 8 CO2Et 2-CF3 imidazol- 1 -yl 10 CO2Et 2-C1 imidazol- 1 -yl 11 CO2Et 2-I imidazol-l-yl 12 CO2Et 2-CF3 pyrazol-1-yl 13 CO2Et 2-Cl pyrazol-1-yl 14 H 2-CF3 1,2,4-triazol-1-yl 19 CO2Et 2-CF3 3-SOMe-I ,2,4-triazol- 1 -yl 20 CO2Et 2-CF3 3-SO2Me- 1 ,2,4-triazol- 1 -yl 21 CO2Et 2-SMe-3-SMe 1,2,4-triazol- 1 -yl 22 CO2Et 2-SMe-3-SMe imidazol-1-yl 23 CO2Et 2-SMe-3-F 1,2,4-triazol-i-yl 24 CO2Et 2-SMe 1 ,2,4-triazol- 1 -yl-3-(1,2,4-triazol- 1 -yl 25 CO2Et 2-SMe-3-Br 1,2,4-triazol-1-yl 26 CO2Et 2-SMe 1,2,4-triazol-i-yl 27 CO2Et 2-SMe imidazol-1-yl 28 CO2Et 2-Et-3-SMe 1,2,4-triazol-1-yl 29 CO2Et 2-iBu 1,2,4-triazol- 1 -yl 30 CO2Et 2-iBu imidazol-1-yl Cpd R (R2)n (XR3)z No. 31 CO2Et 2-SMe-3-OMe 1,2,4-triazol-1-yl 32 CO2Et 2-SMe-3-SMe 1,2,3-triazol-2-yl 33 CO2Et 2-SMe-3-Br 1,2,3-triazol-2-yl 34 CO2Et 2-SMe-3-Br 1,2,3-triazol- 1 -yl 35 CO2Et 2-SMe 1,2,3-triazol-2-yl 36 CO2Et 2-SMe-3-SMe 3-Me-1,2,4-triazol- l-yl 37 CO2Et 2-SMe-3-Br 3 -Me- ,2,4-triazol- 1 -yl 38 CO2Et 2-SMe-3-Br 5-Me-1,2,4-triazol-1-yl 39 CO2Et 2-CH2SMe 1,2,4-triazol-l-yl 40 CO2Et 2-SMe-3-SMe terrazol-1-yl 41 CO2Et 2-SMe tetrazol-1-yl 42 CO2Et 2-Et-3-SMe tetrazol- I -yl 43 CO2Et 2-Et-3-SMe 1,2,3-triazol-2-yl 44 CO2Et 2-Et-3-SMe l,2,3-triazol-i-yl 45 CO2Et 2-iBu 1,2,3-triazol-1-yl 46 CO2Et 2-SMe 3-Me-1,2,4-triazol-1-yl 47 CO2Et 2-Et-3-SMe 3-Me-1,2,4-triazol-1 1 -yl 48 CO2Et 2-iBu 3-Me-1,2,4-triazol-1-yl 50 CO2Et 2-CH2SMe 1,2,4-triazol- 1 -yl 51 H 2-SMe 1,2,4-triazol-1-yl 52 H 2-CH2SMe 1,2,4-triazol-1-yl 53 H 2-SMe-3-F 1 ,2,4-triazol- 1 -yl 54 H 2-Et-3-SMe 1,2,4-triazol-1-yl 55 H 2-iBu 1,2,4-triazol-1-yl 56 H 2-Me 1,2,4-triazol-1-yl 57 H 2-I 1,2,4-triazol-1-yl 58 H 2-SMe-3-Br 1,2,4-triazol-1-yl 59 H 2-C1 1,2,4-triazol-l-yl 60 H 2-SMe-3-SMe 1,2,4-triazol-1-yl 61 CO2Et 2-NO2 1,2,4-triazol-1-yl 62 CO2Et 2-SOMe 1,2,4-triazol-1-yl 63 CO2Et 2-SO2Me 1,2,4-triazol- 1 -yl 64 CO2Et 2-CH2SOMe 1,2,4-triazol- 1 -yl 65 CO2Et 2-CH2SO2Me 1,2,4-triazol- 1 -yl 66 CO2Et 2-SMe-3-Cl 1 ,2,4-triazol- i-yl 67 CO2Et 2-SOMe-3-Cl 1,2,4-triazol-l-yl 68 CO2Et 2-SO2Me-3-Cl 1,2,4-triazol-i-yl 69 CO2Et 2-SOMe-3-OMe 1,2,4-triazol-1-yl 70 CO2Et 2-SO2Me-3-OMe 1,2,4-triazol- 1 -yl 71 CO2Et 2-Br 1,2,4-triazol-1-yl 72 CO2Et 2-OMe 1,2,4-triazol-1-yl Cpd R (R2)n (XR3)z No. 73 CO2Et 2-Me-3-SMe 1,2,4-triazol-1-yl 74 CO2Et 2-Me-3-SOMe 1,2,4-triazol- 1 -yl 75 CO2Et 2-Me-3-SO2Me 1,2,4-triazol- 1 -yl 76 CO2Et 2-OMe-3-SMe 1,2,4-triazol- 1 -yl 77 CO2Et 2-OMe-3-SOMe 1,2,4-triazol-1-yl 78 CO2Et 2-OMe-3-SO2Me 1,2,4-triazol-1-yl 79 CO2Et 2-NmeSO2Me 1,2,4-triazol- 1 -yl 80 CO2Et 2-NmeCO2Me 1,2,4-triazol-1-yl 81 CO2Et 2-CH2Ph 1,2,4-triazol-1-yl 82 CO2Et 2-CH2[(2-MeS)Ph] 1,2,4-triazol- 1 -yl 83 CO2Et 2-CH2[(2-MeSO)Ph] 1,2,4-triazol-1-yl 84 CO2Et 2-CH2[(2-MeSO2)Ph] 1,2,4-triazol-1-yl 85 CO2Et 2-CH2N(Me)SO2Me 1 ,2,4-triazol- 1 -yl 86 CO2Et 2-CH2N(Me)CO2Me 1,2,4-triazol-1-yl 87 CO2Et 2-CH2P(O)(OEt)2 1,2,4-triazol-1 -yl 88 CO2Et - 1 ,2,4-triazol- 1 -yl-2-(1,2,4-triazol- 1 -yl) 89 CO2Et - 1,2,4-triazol-1-yl-2-(imidazol-1-yl) 90 CO2Et 2-N02 1,2,4-triazol-1-yl 91 H 2-SOMe 1 ,2,4-triazol-1 -yl 92 H 2-SO2Me 1 ,2,4-triazol- 1 -yl 93 H 2-CH2SOMe 1,2,4-triazol-1-yl 94 H 2-CH2SO2Me 1,2,4-triazol-1-yl 95 H 2-SMe-3-OMe 1,2,4-triazol-1-yl 96 H 2-SOMe-3-OMe 1,2,4-triazol-1-yl 97 H 2-SO2Me-3-OMe 1,2,4-triazol-1-yl 98 H 2-OMe-3-SMe 1,2,4-triazol-l-yl 99 H 2-OMe-3-SOMe 1,2,4-triazol-1-yl 100 H 2-OMe-3-SO2Me 1,2,4-triazol-1-yl 101 H 2-OMe 1,2,4-triazol-1-yl 102 H - 1 ,2,4-triazol- 1 -yl-2-(1,2,4-triazol- 1 -yl) 103 H - 1,2,4-triazol-1 -yl-2-(imidazol- 1 -yl) 104 H 2-CF3 imidazol-1-yl 105 H 2-SMe imidazol-1-yl 106 H 2-CH2SMe imidazol- 1 -yl 107 H 2-SMe-3-F imidazol-1-yl 108 H 2-Et-3-SMe imidazol-1-yl 109 H 2-iBu imidazol-1-yl 110 H 2-Me imidazol-1-yl 111 H 2-I imidazol-l-yl 112 H 2-SMe-3-Br imidazol-1-yl 113 H 2-C1 imidazol-1-yl Cpd R (R2)n (XR3)z No. 114 H 2-SMe-3-SMe imidazol-1-yl 115 CO2Et 2-CH2SMe imidazol-l-yl 116 CO2Et 2-SMe-3-F imidazol-1-yl 117 CO2Et 2-Et-3-SMe imidazol- l-yI 118 CO2Et 2-Me imidazol-1-yl 119 CO2Et 2-SMe-3-Br imidazol-1-yl 120 CO2Et 2-SMe imidazol-1-yl-3-(1,2,4-triazol-1-yl) 121 H 2-CF3 imidazol-1-yl 122 H 2-SMe imidazol-1-yl 123 H 2-CH2SMe imidazol-1-yl 124 H 2-Me imidazol-1-yl 125 CO2Et 2-CF3 tetrazol- 1 -yl 126 CO2Et 2-CH2SMe tetrazol-1-yl 127 CO2Et 2-SMe-3-F tetrazol- 1 -yl 128 CO2Et 2-iBu tetrazol-1-yl 129 CO2Et 2-Me tetrazol-l-yl 130 CO2Et 2-I tetrazol- 1 -yl 131 CO2Et 2-SMe-3-Br tetrazol- 1 -yl 132 CO2Et 2-C1 tetrazol-1-yl 133 CO2Et 2-SMe tetrazol-1-yl-3-(1,2,4-triazol-1-yl) 134 H 2-CF3 tetrazol-1-yl 135 H 2-SMe tetrazol- 1 -yl 136 H 2-CH2SMe tetrazol-1-yl 137 H 2-Me tetrazol-1-yl 138 CO2Et 2-CF3 benzimidazol-1-yl 139 CO2Et 2-SMe benzimidazol-1-yl 140 CO2Et 2-CH2SMe benzimidazol- 1-yl 141 CO2Et 2-SMe-3-F benzimidazol- 1 -yl 142 CO2Et 2-Et-3-SMe benzimidazol-l-yl 143 CO2Et 2-iBu benzimidazol-1-yl 144 CO2Et 2-Me benzimidazol-1-yl 145 CO2Et 2-I benzimidazol- 1 -yl 146 CO2Et 2-SMe-3-Br benzimidazol-1-yl 147 CO2Et 2-C1 benzimidazol-1-yl 148 CO2Et 2-SMe-3-SMe benzimidazol- 1 -yl 149 CO2Et 2-SMe benzimidazol- 1 -yl-3-(1,2,4-triazol-1-yl) 150 H 2-CF3 benzimidazol- 1 -yl 151 H 2-SMe benzimidazol-1-yl 152 H 2-CH2SMe benzimidazol-1-yl 153 H 2-Me benzimidazol-l-yl 154 CO2Et 2-CF3 1,2,3-triazol-1-yl Cpd R (R2)n (XR3)z No. 155 CO2Et 2-SMe 1,2,3-triazol-1-yl 156 CO2Et 2-CH2 SMe 1,2,3-triazol-1-yl 157 CO2Et 2-SMe-3-F 1,2,3-triazol-1-yl 158 CO2Et 2-Me 1 ,2,3-triazol- 1-yl 159 CO2Et 2-I 1,2,3-triazol-1-yl 160 CO2Et 2-C1 1,2,3-triazol-1-yl 161 CO2Et 2-SMe-3-SMe 1,2,3-triazol-1-yl 162 CO2Et 2-SMe 1 ,2,3-triazol- 1 yl-3-(1 ,2,4-triazol- 1 -yl) 163 H 2-CF3 1 ,2,3-triazol- 1 -yl 164 H 2-SMe 1,2,3-triazol-1-yl 165 H 2-CH2SMe 1,2,3-triazol-1-yl 166 H 2-Me 1,2,3-triazol-1-yl 167 CO2Et 2-CF3 1,2,3-triazol-2-yl 168 CO2Et 2-CH2SMe 1 ,2,3-triazol-2-yl 169 CO2Et 2-SMe-3-F 1,2,3-triazol-2-yl 170 CO2Et 2-iBu 1,2,3-triazol-2-yl 171 CO2Et 2-Me 1 1,2,3-triazol-2-yl 172 CO2Et 2-I 1 ,2,3-triazol-2-yl 173 CO2Et 2-C1 1 ,2,3-triazol-2-yl 174 CO2Et 2-SMe 1,2,3 ,2,3-triazol-2-yl-3-( 1 2,4-triazol- 1 -yl) 175 H 2-CF3 1 ,2,3-triazol-2-yl 176 H 2-SMe 1,2,3-triazol-2-yl 177 H 2-CH2SMe 1,2,3-triazol-2-yl 178 H 2-Me 1 ,2,3-triazol-2-yl 179 CO2Et 2-CF3 3-Methylpyrazol-1-yl 180 CO2Et 2-SMe 3-Methylpyrazol- 1 -yl 181 CO2Et 2-CH2SMe 3-Methylpyrazol- 1 -yl 182 CO2Et 2-Me 3-Methylpyrazol-1-yl 183 CO2Et 2-CF3 benzotriazol- 1 -yl 184 CO2Et 2-SMe benzotriazol- 1 -yl 185 CO2Et 2-CH2SMe benzotriazol- 1 -yl 186 CO2Et 2-Me benzotriazol-1 -yI 187 CO2Et 2-CF3 benzotriazol-2-yl 188 CO2Et 2-SMe benzotriazol-2-yl 189 CO2Et 2-CH2SMe benzotriazol-2-yl 190 CO2Et 2-Me benzotriazol-2-yl 191 CO2Et 2-CF3 5-MeS-tetrazol- 1 -yl 192 CO2Et 2-SMe 5-MeS-tetrazol-1-yl 193 CO2Et 2-CH2SMe 5-MeS-tetrazol- 1 -yl 194 CO2Et 2-Me 5-MeS-tetrazol- 1 -yl 195 CO2Et 2-CD3 5-MeS-tetrazol-1-yl Cpd R (R2)n (XR3)z No. 196 CO2Et 2-SMe 5 -MeS-tetrazol- 1 -yl 197 CO2Et 2-CH2SMe 5-MeS-tetrazol-1-yl 198 CO2Et 2-Me 5-MeS-tetrazol-1-yl 199 CO2Et 2-CF3 indol- l-yI 200 CO2Et 2-SMe indol-l-yl 201 CO2Et 2-CII2SMe indol-1-yl 202 CO2Et 2-Me indol-1-yl 203 CO2Et 2-SMe pyrazol-1-yl 204 CO2Et 2-CH2SMe pyrazol-1-yl 205 CO2Et 2-Me pyrazol-1-yl 206 CO2Et 2-CF3 2-NO2-imidazol- 1 -yl 207 CO2Et 2-CF3 4-N02-imidazol-1-yl 208 CO2Et 2-CF3 3 -Et-imidazol- I-yl 209 CO2Et 2-CF3 4-CO2Me-imidazol-l-yl 210 CO2Et 2-CF3 5-SMe-tetrazol-1-yl 211 CO2Et 2-CF3 indazol-l-yl 428 H 2,3-SCH2CH2O- 1 ,2,4-triazol- 1 -yl 429 CO2Et 2,3-SCH2CH20- 1,2,3,4-tetrazol-1-yl 430 CO2Et 2,3-SCH2CH2O- 1,2,3-triazol-1-yl 431 CO2Et 2-SMe-3-OMe 1,2,3-triazol-1-yl 432 CO2Et 2,3-SCH2CH20- benz- 1,2,3 -triazol- 1 -yl 433 CO2Et 2-SMe-3-OMe imidazol-1-yl 434 CO2Et 2-iBu 5-Me-1,2,4-triazol-1-yl 435 CO2Et 2-F 1,2,4-triazol-1-yl 436 H 2-F 1 ,2,4-triazol- 1 -yl 437 H 2-Br 1,2,4-triazol-1-yl TABLE 2 Cpd. R (R2)n (XR3)z No. 15 H - 1,2,4-triazol-1-yl 16 H - pyrazol- l-yl 17 CO2Et - 1,2,4-triazol-1-yl 18 CO2Et 4-CF3 1,2,4-triazol-1-yl 212 CO2Et 4-SMe 1,2,4-triazol-1-yl 213 CO2Et 4-F 1,2,4-triazol-1-yl 214 CO2Et 4-Cl 1,2,4-triazol-1-yl 215 CO2Et 4-Br 1,2,4-triazol-1-yl 216 CO2Et 4-I 1,2,4-triazol-1-yl 217 CO2Et 4-Me 1,2,4-triazol-1-yl 218 CO2Et 4-OMe 1,2,4-triazol-1-yl Cpd. R (R2)n (XR3)z No. 219 CO2Et 4-SOMe 1,2,4-triazol-1-yl 220 CO2Et 4-SO2Me 1,2,4-triazol- 1 -yl 221 CO2Et 3-SMe 1,2,4-triazol-1-yl 222 CO2Et 3-CF3 1,2,4-triazol- 1 -yl 223 CO2Et 3-SMe-4-F 1,2,4-triazol-1-yl 224 CO2Et 3-F 1,2,4-triazol-1-yl 225 CO2Et 3-Cl 1,2,4-triazol-1-yl 226 CO2Et 3-Br 1,2,4-triazol-1-yl 227 CO2Et 3-I 1,2,4-triazol-1-yl 228 CO2Et 3-Me 1,2,4-triazol- 1 -yl 229 CO2Et 3-OMe 1,2,4-triazol-1-yl 230 CO2Et 3-SOMe 1,2,4-triazol-1-yl 231 CO2Et 3-SO2Me 1,2,4-triazol-1-yl 232 CO2Et 3-SOMe-4-F 1,2,4-triazol-1-yl 233 CO2Et 3-SO2Me-4-F 1,2,4-triazol-1 -yl 234 CO2Et 3-SMe-4-OMe 1,2,4-triazol-1-yl 235 CO2Et 3-SOMe4-OMe 1,2,4-triazol-1-yl 236 CO2Et 3-SO2Me-4-OMe 1,2,4-triazol-1 -yl 237 CO2Et 3-SMe-4-SMe 1,2,4-triazol-1-yl 238 CO2Et 3-SO2Me-4-SO2Me 1,2,4-triazol-1-yl 239 CO2Et 3-Me-4-F 1,2,4-triazol-1-yl 240 CO2Et 3-Me-4-SMe 1,2,4-triazol-1-yl 241 CO2Et 3-CH2SOMe 1,2,4-triazol-1-yl 242 CO2Et 3-CH2SO2Me 1 ,2,4-triazol- 1-yl 243 CO2Et 3,4-C12 1,2,4-triazol-1-yl 244 CO2Et 3,4-F2 1,2,4-triazol-1-yl 245 CO2Et 3-CH2SO2Me 1,2,4-triazol-1-yl 246 H 4-CF3 1,2,4-triazol-1-yl 247 H 4-SMe 1,2,4-triazol-1-yl 248 H 4-F 1,2,4-triazol-1-yl 249 H 4-Cl 1,2,4-triazol-1-yl 250 H 4-Br 1,2,4-triazol-1-yl 251 H 4-I 1,2,4-triazol-1-yl 252 H 4-Me 1,2,4-triazol-1-yl 253 H 4-OMe 1,2,4-triazol-1-yl 254 H 4-SOMe 1,2,4-triazol-1-yl 255 H 4-SO2Me 1,2,4-triazol-1-yl 256 H 3-SMe 1,2,4-triazol-1-yl 257 H 3-CF3 1 ,2,4-triazol-1 -yl 258 H 3-SMe-4-F 1,2,4-triazol-1-yl Cpd. R (R2)n (XR3)z No. 259 H 3-F 1,2,4-triazol- 1 -yl 260 H 3-Cl 1,2,4-triazol-1-yl 261 H 3-Br 1,2,4-triazol-1-yl 262 H 3-I 1 ,2,4-triazol- l-yl 263 H 3-Me 1,2,4-triazol- 1 -yl 264 H 3-OMe 1,2,4-triazol-1-yl 265 H 3-SOMe 1,2,4-triazol-1-yl 266 H 3-SO2Me 1,2,4-triazol-1-yl 267 H 3-SOMe-4-F 1,2,4-triazol-1-yl 268 H 3-SO2Me-4-F 1,2,4-triazol-1-yl 269 H 3 -SMe-4-OMe 1,2,4-triazol-1-yl 270 H 3 -SOMe-4-OMe 1,2,4-triazol- 1 -yl 271 H 3-SO2Me-4-OMe 1,2,4-triazol-1-yl 272 H 3-SMe-4-SMe 1,2,4-triazol-1-yl 273 H 3-SO2Me-4-SO2Me 1,2,4-triazol-1-yl 274 H 3-Me-4-F 1,2,4-triazol-1-yl 275 H 3-Me4-SMe 1,2,4-triazol-1-yl 276 H 3-CH2SOMe 1,2,4-triazol-1-yl 277 H 3-CH2SO2Me 1,2,4-triazol-1-yl 278 H 3,4-C12 1,2,4-triazol-1-yl 279 H 3,4-F2 1,2,4-triazol-1-yl 280 H 3-CH2SO2Me 1,2,4-triazol-l-yl 281 CO2Et 4-CF3 imidazol- 1 -yl 282 CO2Et 4-SMe imidazol- 1 -yl 283 CO2Et 4-F imidazol-1-yl 284 CO2Et 4-Cl imidazol- 1 -yl 285 CO2Et 4-Br imidazol-l-yl 286 H 4-CF3 imidazol-1-yl 287 H 4-SMe imidazol- 1 -yl 288 H 4-F imidazol-l-yl 289 H 4-C1 imidazol-l-yl 290 H 4-Br imidazol-l-yl 291 CO2Et 4-CF3 tetrazol-1-yl 292 CO2Et 4-SMe tetrazol-1-yl 293 CO2Et 4-F tetrazol-1-yl 294 CO2Et 4-Cl tetrazol-l-yl 295 CO2Et 4-Br tetrazol-1-yl 296 H 4-CF3 tetrazol-l-yl 297 H 4-SMe tetrazol-l-yl 298 H 4-F tetrazol-l-yl Cpd. R (R2)n (XR3)z No. 299 H 4-Cl tetrazol-1-yl 300 H 4-Br tetrazol- l-yl 301 CO2Et 4-CF3 benzimidazol-1-yl 302 CO2Et 4-SMe benzimidazol-l-yl 303 CO2Et 4-F benzimidazol-1-yl 304 CO2Et 4-Cl benzimidazol-1-yl 305 CO2Et 4-Br benzimidazol-l-yl 306 H 4-CF3 benzimidazol-1-yl 307 H 4-SMe benzimidazol-1-yl 308 H 4-F benzimidazol-l-yl 309 H 4-Cl benzimidazol-1-yl 310 H 4-Br benzimidazol- l-yl 311 CO2Et 4-CF3 1,2,3-triazol-l-yl 312 CO2Et 4-SMe 1,2,3-triazol-1-yl 313 CO2Et 4-F 1,2,3-triazol-1 -yl 314 CO2Et 4-Cl 1,2,3-triazol-1-yl 315 CO2Et 4-Br 1,2,3-triazol-1-yl 316 H 4-CF3 1,2,3-triazol-1-yl 317 H 4-SMe 1,2,3-triazol-1-yl 318 H 4-F 1,2,3-triazol-1-yl 319 H 4-Cl 1,2,3-triazol-1-yl 320 H 4-Br 1,2,3-triazol-1-yl 321 CO2Et 4-CF3 1,2,3-triazol-2-yl 322 CO2Et 4-SMe 1,2,3-triazol-2-yl 323 CO2Et 4-F 1,2,3-triazol-2-yl 324 CO2Et 4-C1 1,2,3-triazol-2-yl 325 CO2Et 4-Br 1,2,3 -triazol-2-yl 326 H 4-CF3 1,2,3-triazol-2-yl 327 H 4-SMe 1,2,3-triazol-2-yl 328 H 4-F 1,2,3-triazol-2-yl 329 H 4-Cl 1,2,3-triazol-2-yl 330 H- 4-Br 1,2,3-triazol-2-yl TABLE 3 Cpd R (R2)n (XR3)z No. 331 H - 1,2,4-triazol-1-yl 332 CO2Et - 1,2,4-triazol-1-yl 333 CO2Et 2-CF3 1,2,4-triazol-1-yl Cpd R (R2)n (XR3)z No. 334 CO2Et 2-SMe 1,2,4-triazol-1 -yl 335 CO2Et 2-F 1,2,4-triazol-l-yl 336 CO2Et 2-Cl 1,2,4-triazol-1-yl 337 CO2Et 2-Br 1,2,4-triazol-1-yl 338 CO2Et 2-SOMe 1,2,4-triazol-1 -yl 339 CO2Et 2-SO2Me 1,2,4-triazol-1-yl 340 CO2Et - 1 ,2,4-triazol- 1 -yl-2-(1,2,4-triazol- 1 -yl) 341 CO2Et 2-SMe-4-CF3 1,2,4-triazol-1-yl 342 CO2Et 2-SMe-4-F 1,2,4-triazol-1-yl 343 CO2Et 2-SMe-4-Br 1,2,4-triazol-1-yl 344 CO2Et 2-SMe-4-Cl 1,2,4-triazol-1-yl 345 CO2Et 4-Cl 1 ,2,4-triazol- 1 -yl-2-(1,2,4-triazol- 1 -yl) 346 CO2Et 2-SO2Me-4-SO2Me 1,2,4-triazol-1-yl 347 CO2Et 2-SMe-4-SMe 1,2,4-triazol-l-yl 348 CO2Et 2-CH2SMe 1,2,4-triazol-l-yl 349 H 2-CF3 1,2,4-triazol-l-yl 350 H 2-SMe 1,2,4-triazol-1-yl 351 H 2-SO2Me 1,2,4-triazol-1-yl 352 H - imidazol- 1 -yl 353 CO2Et - imidazol-1-yl 354 CO2Et 2-CF3 imidazol-l-yl 355 CO2Et 2-SMe imidazol-1-yl 356 CO2Et 2-F imidazol-l-yl 357 CO2Et 2-Cl imidazol- 1 -yl 358 CO2Et 2-Br imidazol-l-yl 359 CO2Et 2-SOMe imidazol-l-yl 360 CO2Et 2-SO2Me imidazol-1-yl 361 CO2Et - imidazol-1-yl-2-(1,2,4-triazol-1-yl) 362 CO2Et 2-SMe-4-CF3 imidazol-1-yl 363 CO2Et 2-SMe-4-F imidazol-1-yl 364 CO2Et 2-SMe-4-Br imidazol-l-yl 365 CO2Et 2-SMe-4-Cl imidazol-1-yl 366 CO2Et 4-Cl imidazol-1-yl-2-(1,2,4-triazol-1-yl) 367 CO2Et 2-SO2Me4-SO2Me imidazol- 1 -yl 368 CO2Et 2-SMe-4-SMe imidazol- 1 -yl 369 CO2Et 2-CH2SMe imidazol-1-yl 370 H 2-CF3 imidazol-1-yl 371 H 2-SMe imidazol-1-yl 372 H 2-SO2Me imidazol-1-yl 373 H - tetrazol-1-yl Cpd R (R2)n (XR3)z No. 374 CO2Et - tetrazol-l-yl 375 CO2Et 2-CF3 tetrazol-1-yl 376 CO2Et 2-SMe tetrazol-l-yl 377 CO2Et 2-F tetrazol-1-yl 378 CO2Et 2-Cl tetrazol-l-yl 379 CO2Et 2-Br tetrazol-1-yl 380 CO2Et 2-SOMe tetrazol-l-yl 381 CO2Et 2-SO2Me tetrazol-l-yl 382 CO2Et - tetrazol-1-yl-2-(1,2,4-triazol-1-yl) 383 CO2Et 2-SMe-4-CF3 tetrazol-l-yl 384 CO2Et 2-SMe-4-F tetrazol- 1 -yl 385 CO2Et 2-SMe-4-Br tetrazol-l-yl 386 CO2Et 2-SMe-4-Cl tetrazol-l-yl 387 CO2Et 4-Cl tetrazol-1-yl-2-(1,2,4-triazol-1-yl) 388 CO2Et 2-SO2Me4-SO2Me tetrazol-l -yl 389 CO2Et 2-SMe-4-SMe tetrazol-1-yl 390 CO2Et 2-CH2SMe tetrazol-1-yl 391 H 2-CF3 tetrazol-l-yl 392 H 2-SMe tetrazol-l-yl 393 H 2-SO2Me tetrazol-l-yl 394 H - 1,2,3-triazol-1-yl 395 CO2Et - 1,2,3-triazol-l-yl 396 CO2Et 2-CF3 1,2,3-triazol- 1 -yl 397 CO2Et 2-SMe 1,2,3-triazol- 1 -yl 398 CO2Et 2-F 1,2,3-triazol-l-yl 399 CO2Et 2-C1 1,2,3-triazol-1-yl 400 CO2Et 2-Br 1,2,3-triazol- 1 -yl 401 CO2Et 2-SOMe 1,2,3-triazol-1-yl 402 CO2Et 2-SO2Me 1,2,3-triazol-1-yl 403 CO2Et - 1 ,2,3-triazol- 1 -yl-2-(1,2,4-triazol-1-yl) 404 CO2Et 2-SMe-4-CF3 1,2,3-triazol-1-yl 405 CO2Et 2-SMe4-F 1,2,3-triazol-1-yl 406 CO2Et 2-SMe-4-Br 1,2,3 -triazol- 1 -yl 407 CO2Et 2-SMe-4-Cl 1,2,3-triazol-1-yl 408 CO2Et 4-C1 1 ,2,3-triazol- 1 -yl-2-(1,2,4-triazol- 1 -yl) 409 CO2Et 2-SO2Me-4-SO2Me 1,2,3-triazol-1-yl 410 CO2Et 2-SMe-4-SMe 1,2,3-triazol-1-yl 411 CO2Et 2-CH2SMe 1,2,3-triazol-1-yl 412 H 2-CF3 1,2,3-triazol-1-yl 413 H 2-SMe 1,2,3-triazol-1-yl

Cpd R (R2)n (XR3)z No. 414 H 2-SO2Me 1,2,3-triazol-1-yl The following compounds of formula (Ie) wherein n represents 0 or 1 shown in Table 4 also form part of the invention.

TABLE 4 Cpd.No. R (R2)n (XR3)z 3 CO2Et H 4-(1,2,4-triazol-1-yl) 9 CO2Et H 4-(imidazol-1-yl) 415 CO2Et H 2-(1,2,4-triazol-1-yl) 416 CO2Et H 3-(1,2,4-triazol-1-yl) 417 H H 4-(1,2,4-triazol-1-yl) 418 H H 4-(imidazol-1-yl) 419 H H 2-(1,2,4-triazol-1-yl) 420 H H 3-(1,2,4-triazol-1-yl) The following compounds of formula (Ic) shown in Table 5 wherein R1 represents cyclopropyl also form part of the invention.

TABLE 5 Cpd.No. (R2)n (R3)x 49 2-CF3 4-(1,2,4-triazol-1-yl) 421 2-SMe 4-(1,2,4-triazol-1-yl) 422 2-Cl 4-(1,2,4-triazol-1-yl) 423 2-Me 4-(1,2,4-triazol-1-yl) 424 4-CF3 2-(1,2,4-triazol-1-yl) 425 4-SMe 2-(1,2,4-triazol-1-yl) 426 4-Cl 2-(1,2,4-triazol-1-yl) 427 4-Me 2-(1,2,4-triazol-1-yl)

The following compounds of formula (Id) in which Ra represents methyl, and the group (XR3)z is attached either to the 4-position of the phenyl ring (Table 6), or to the 2-position of the phenyl ring (Table 7), or to the 3-position of the phenyl ring (Table 8), also form part of the present invention.

TABLE 6 Cpd Rb Q (R2)n (XR3)z No. 501 Me H 2-CF3 1,2,4-triazol- 1 -yl 502 Me CH2COPh 2-CF3 1,2,4-triazol- 1 -yl 503 Me Me 2-CF3 1,2,4-triazol- 1 -yl 504 Me Et 2-CF3 1 ,2,4-triazol-1 -yl 505 Me iPr 2-CF3 1,2,4-triazol- 1 -yl 506 Me CH2Ph 2-CF3 1,2,4-triazol- 1 -yl 507 Me CH2CO2Me 2-CF3 1,2,4-triazol-1-yl 508 Me CH(CO2Me)Me 2-CF3 1,2,4-triazol-1-yl 509 Me CH2CH=CH2 2-CF3 1,2,4-triazol-1-yl 510 Me prop-2-ynyl 2-CF3 1,2,4-triazol-1-yl 511 Me SO2Ph 2-CF3 1,2,4-triazol-1-yl 512 Me COMe 2-CF3 1,2,4-triazol-1-yl 513 Me COPh 2-CF3 1,2,4-triazol-1-yl 514 Me COtBu 2-CF3 1,2,4-triazol-1-yl 515 Me SO2(4-Me Ph) 2-CF3 1,2,4-triazol-1-yl 516 Me S02iPr 2-CF3 1,2,4-triazol-1-yl 517 H H 2-CF3 1,2,4-triazol-1-yl 518 Me CH2CO(4-Me Ph) 2-CF3 1,2,4-triazol-1-yl 519 Me S02(4-Me Ph) 2-CF3 1,2,3-triazol-1-yl 520 Me SO2(4-Me Ph) 2-CH2SMe 1,2,3-triazol-1-yl 521 Me SO2(4-Me Ph) 2-C1 1,2,3-triazol-1-yl 522 Me S02(4-Me Ph) 2-Me 1,2,3-triazol-1-yl 523 Me S02(4-Me Ph) 2-SMe 1,2,3-triazol-14l 524 Me S02(4-Me Ph) 2-SMe-3-Br 1,2,3-triazol-1-yl 525 Me S02(4-Me Ph) 2-SMe-3-F 1,2,3-triazol-1-yl 526 Me SO2(4-Me Ph) 2-SMe-3-SMe 1,2,3-triazol-1-yl 527 Me S02(4-Me Ph) 2-CF3 1,2,3-triazol-2-yl 528 Me S02(4-Me Ph) 2-CH2SMe 1,2,3-triazol-2-yl 529 Me S02(4-Me Ph) 2-Cl 1,2,3-triazol-2-yl 530 Me S02(4-Me Ph) 2-Me 1 ,2,3-triazol-2-y1 531 Me S02(4-Me Ph) 2-SMe 1,2,3-triazol-2-yl 532 Me SO2(4-Me Ph) 2-SMe-3-Br 1,2,3-triazol-2-yl Cpd Rb Q (R2)n (XR3)z No. 533 Me SO2(4-Me Ph) 2-SMe-3-F 1,2,3-triazol-2-yl 534 Me SO2(4-Me Ph) 2-SMe-3-SMe 1,2,3-triazol-2-yl 535 Me SO2(4-Me Ph) 2-Br 1,2,4-triazol-1-yl 536 Me SO2(4-Me Ph) 2-CH2[(2-MeS)Ph] l,2,4-triazol-1-yl 537 Me S02(4-Me Ph) 2-CH2[(2-MeSO)Ph] 1,2,4-triazol-1-yl 538 Me S02(4-Me Ph) 2-CH2[(2-MeSO2)Ph] 1,2,4-triazol-1-yl 539 Me S02(4-Me Ph) 2-CH2N(Me)CO2Me 1,2,4-triazol-1-yl 540 Me S02(4-Me Ph) 2-CH2N(Me)SO2Me 1 ,2,4-triazol- 1 -yl 541 Me S02(4-Me Ph) 2-CH2Ph 1,2,4-triazol-1-yl 542 Me SO2(4-Me Ph) 2-CH2SMe 1,2,4-triazol-1-yl 543 Me CH2CO(4-Me Ph) 2-CH2SMe 1,2,4-triazol-1-yl 544 Me S02(4-Me Ph) 2-CH2SO2Me 1,2,4-triazol-1-yl 545 Et S02(4-Me Ph) 2-CH2SOMe 1,2,4-triazol-1-yl 546 Me S02(4-Me Ph) 2-Cl 1,2,4-triazol-1-yl 547 Me S02(4-Me Ph) 2-Me 1,2,4-triazol-1-yl 548 Me S02(4-Me Ph) 2-Me-3-SMe 1,2,4-triazol-1-yl 549 Me S02(4-Me Ph) 2-Me-3-SO2Me 1,2,4-triazol-1-yl 550 Me S02(4-Me Ph) 2-Me-3-SOMe 1,2,4-triazol-1-yl 551 Me S02(4-Me Ph) 2-NMeCO2Me 1,2,4-triazol-1-yl 552 Me S02(4-Me Ph) 2-NMeSO2Me 1,2,4-triazol-1-yl 553 Me SO2(4-Me Ph) 2-OMe 1,2,4-triazol-1-yl 554 Me SO2(4-Me Ph) 2-OMe-3-SMe 1,2,4-triazol-1-yl 555 Me S02(4-Me Ph) 2-OMe-3-SO2Me 1,2,4-triazol-1-yl 556 Me SO2(4-Me Ph) 2-OMe-3-SOMe 1,2,4-triazol-1-yl 557 Me SO2(4-Me Ph) 2-SMe 1,2,4-triazol-1-yl 558 Me 02(4-Me Ph) 2-SMe-3-Br 1,2,4-triazol-1-yl 559 Me SO2(4-Me Ph) 2-SMe-3-Cl 1,2,4-triazol-1-yl 560 Me S02(4-Me Ph) 2-SMe-3-F 1,2,4-triazol-1-yl 561 Me SO2(4-Me Ph) 2-SMe-3-OMe 1,2,4-triazol-1-yl 562 Me SO2(4-Me Ph) 2-SMe-3-SMe 1,2,4-triazol-1-yl 563 Me SO2(4-Me Ph) 2-SO2Me 1,2,4-triazol-1-yl 564 Me SO2(4-Me Ph) 2-SO2Me-3-Cl 1,2,4-triazol-1-yl 565 Me SO2(4-Me Ph) 2-SO2Me-3-OMe 1,2,4-triazol-1-yl 566 Me SO2(4-Me Ph) 2-SOMe 1,2,4-triazol-1-yl 567 Me SO2(4-Me Ph) 2-SOMe-3-Cl 1,2,4-triazol-1-yl 568 Me SO2(4-Me PH) 2-SOMe-3-OMe 1,2,4-triazol-l-yl 569 Me 02(4-Me Ph) 2-N02 1,2,4-triazol-1-yl 570 Me SO2(4-Me Ph) 2-CF3 imidazol-1-yl 571 Me SO2(4-Me Ph) 2-CH2SMe imidazol-1-yl 572 Me SO2(4-Me Ph) 2-Cl imidazol-1-yl 573 Me SO2(4-Me Ph) 2-Me imidazol-1-yl Cpd Rb Q (R2)n (XR3)z No. 574 Me SO2(4-Me Ph) 2-SMe imidazol-1-yl 575 Me SO2(4-Me Ph) 2-SMe-3-Br imidazol-l-yl 576 Me SO2(4-Me Ph) 2-SMe-3-F imidazol-1-yl 577 Me SO2(4-Me Ph) 2-SMe-3-SMe imidazol-1-yl 578 Me S02(4-Me Ph) 2-CF3 pyrazol-l-yl 579 Me SO2(4-Me Ph) 2-CH2SMe pyrazol-1-yl 580 Me SO2(4-Me Ph) 2-Cl pyrazol-1-yl 581 Me SO2(4-Me Ph) 2-Me pyrazol-1-yl 582 Me SO2(4-Me Ph) 2-SMe pyrazol-l-yl 583 Me SO2(4-Me Ph) 2-CF3 tetrazol-1-yl 584 Me SO2(4-Me Ph) 2-SMe tetrazol-1-yl 585 Me SO2(4-Me Ph) 2-SMe-3-SMe tetrazol-1-yl 586 Me CH2CO(4-Me Ph) 2-CF3 1,2,3-triazol-1-yl 587 Me CH2CO(4-Me Ph) 2-CH2SMe 1,2,3-triazol-1-yl 588 Me CH2CO(4-Me Ph) 2-C1 1,2,3-triazol-1-yl 589 Me CH2CO(4-Me Ph) 2-Me 1,2,3-triazol-1-yl 590 Me CH2CO(4-Me Ph) 2-SMe 1,2,3-triazol-l-yl 591 Me CH2CO(4-Me Ph) 2-SMe-3-Br 1,2,3-triazol-1-yl 592 Me CH2CO(4-Me Ph) 2-SMe-3-F 1,2,3-triazol-1-yl 593 Me CH2CO(4-Me Ph) 2-SMe-3-SMe 1,2,3-triazol-1-yl 594 Me CH2CO(4-Me Ph) 2-CF3 1 ,2,3-triazol-2-yl 595 Me CH2CO(4-Me Ph) 2-CH2SMe 1,2,3-triazol-2-yl 596 Me CH2CO(4-Me Ph) 2-Cl 1,2,3-triazol-1-yl 597 Me CH2CO(4-Me Ph) 2-Me 1,2,3-triazol-1-yl 598 Me CH2CO(4-Me Ph) 2-SMe 1,2,3-triazol-2-yl 599 Me CH2CO(4-Me Ph) 2-SMe-3-Br 1,2,3-triazol-2-yl 600 Me CH2CO(4-Me Ph) 2-SMe-3-F 1,2,3-triazol-2-yl 601 Me CH2CO(4-Me Ph) 2-SMe-3-SMe 1,2,3-triazol-2-yl 602 Me CH2CO(4-Me Ph) 2-Br 1,2,4-triazol-1-yl 603 Et SO2(4-Me Ph) 2-CF3 1,2,4-triazol-1-yl 604 Me CH2CO(4-Me Ph) 2-CH2[(2-MeS)Ph] 1,2,4-triazol-1-yl 605 Me CH2CO(4-Me Ph) 2-CH2[(2-MeSO)Ph] 1,2,4-triazol-1-yl 606 Me CH2CO(4-Me Ph) 2-CH2[(2-MeSO2)Ph] 1,2,4-triazol-1-yl 607 Me CH2CO(4-Me Ph) 2-CH2N(Me)CO2Me 1 ,2,4-triazol- 1 -yl 608 Me CH2CO(4-Me Ph) 2-CH2N(Me)SO2Me 1,2,4-triazol-1-yl 609 Me CH2CO(4-Me Ph) 2-CH2Ph l,2,4-triazol-1-yl 610 Me CH2(4-Me Ph) 2-CH2SMe 1,2,4-triazol-1-yl 611 Et SO2(4-Me Ph) 2-CH2SMe 1,2,4-triazol-1-yl 612 Me CH2CO(4-Me Ph) 2-CH2SO2Me 1,2,4-triazol-1-yl 613 Et CH2CO(4-Me Ph) 2-CH2SOMe 1,2,4-triazol-1-yl 614 Me CH2CO(4-Me Ph) 2-C1 1,2,4-triazol-1-yl Cpd Rb Q (R2)n (XR3)z No. 615 Me CH2CO(4-Me Ph) 2-Me 1,2,4-triazol-1-yl 616 Me CH2CO(4-Me Ph) 2-Me-3-SMe 1,2,4-triazol-1-yl 617 Me CH2CO(4-Me Ph) 2-Me-3-SO2Me 1,2,4-triazol-1-yl 618 Me CH2CO(4-Me Ph) 2-Me-3-SOMe 1,2,4-triazol-1-yl 619 Me CH2CO(4-Me Ph) 2-NMeCO2Me 1,2,4-triazol-1-yl 620 Me CH2CO(4-Me Pb) 2-NMeSO2Me # 1,2,4-triazol-1-yl 621 Me CH2CO(4-Me Ph) 2-OMe 1,2,4-triazol-1-yl 622 Me CH2CO(4-Me Ph) 2-OMe-3-SMe 1,2,4-triazol-1-yl 623 Me CH2CO(4-Me Ph) 2-OMe-3-SO2Me 1,2,4-triazol-1-yl 624 Me CH2CO(4-Me Ph) 2-OMe-3-SOMe 1,2,4-triazol-1-yl 625 Me CH2CO(4-Me Ph) 2-SMe 1,2,4-triazol-1-yl 626 Me CH2CO(4-Me Ph) 2-SMe-3-Br 1,2,4-triazol-1-yl 627 Me CH2CO(4-Me Ph) 2-SMe-3-Cl 1,2,4-triazol-l-yl 628 Me CH2CO(4-Me Ph) 2-SMe-3-F 1,2,4-triazol-1-yl 629 Me CH2CO(4-Me Ph) 2-SMe-3-OMe 1 ,2,4-triazol- 1 -yl 630 Me CH2CO(4-Me Ph) 2-SMe-3-SMe 1,2,4-triazol-1-yl 631 Me CH2CO(4-Me Ph) 2-SO2Me 1 ,2,4-triazol- 1 -yl 632 Me CH2CO(4-Me Ph) 2-SO2Me-3-Cl 1 ,2,4-triazol-1 -yl 633 Me CH2CO(4-Me Ph) 2-SO2Me-3-OMe 1,2,4-triazol-1-yl 634 Me CH2CO(4-Me Ph) 2-SOMe 1,2,4-triazol-l-yl 635 Me CH2CO(4-Me Ph) 2-SOMe-3-Cl 1,2,4-triazol-1-yl 636 Me CH2CO(4-Me Ph) 2-SOMe-3-OMe 1,2,4-triazol-l-yl 637 Me CH2CO(4-Me Ph) 2-NO2 1,2,4-triazol-1-yl 638 Me CH2CO(4-Me Ph) 2-CF3 imidazol-l-yl 639 Me CH2CO(4-Me Ph) 2-CH2SMe imidazol-l-yl 640 Me CH2CO(4-Me Ph) 2-Cl imidazol-1-yl 641 Me CH2CO(4-Me Ph) 2-Me imidazol- 1 -yl 642 Me CH2CO(4-Me Ph) 2-SMe imidazol-l-yl 643 Me CH2CO(4-Me Ph) 2-SMe-3-Br imidazol-1-yl 644 Me CH2CO(4-Me Ph) 2-SMe-3-F imidazol-1-yl 645 Me CH2CO(4-Me Ph) 2-SMe-3-SMe imidazol-l-yl 646 Me CH2CO(4-Me Ph) 2-CF3 pyrazol-1-yl 647 Me CH2CO(4-Me Ph) 2-CH2SMe pyrazol-1-yl 648 Me CH2CO(4-Me Ph) 2-Cl pyrazol-1-yl 649 Me CH2CO(4-Me Ph) 2-Me pyrazol-1-yl 650 Me CH2CO(4-Me Ph) 2-SMe pyrazol-l-yl 651 Me CH2CO(4-Me Ph) 2-CF3 tetrazol-1-yl 652 Me CH2CO(4-Me Ph) 2-SMe tetrazol-l-yl 653 Me CH2CO(4-Me Ph) 2-SMe-3-SMe tetrazol-1-yl 654 Me CH2(4-Me Ph) 2-CF3 1,2,3-triazol-1-yl 655 Me CH2(4-Me Ph) 2-CH2SMe 1,2,3-triazol-1-yl Cpd Rb Q (R2)n (XR3)z No. 656 Me CH2(4-Me Ph) 2-Cl 1,2,3-triazol-1-yl 657 Me CH2(4-Me Ph) 2-Me 1,2,3-triazol-1-yl 658 Me CH2(4-Me Ph) 2-SMe 1,2,3-triazol-1-yl 659 Me CH2(4-Me Ph) 2-SMe-3-Br 1,2,3-triazol-l-yl 660 Me CH2(4-Me Ph) 2-SMe-3-F 1,2,3-triazol-1-yl 661 Me CH2(4-Me Ph) 2-SMe-3-SMe 1,2,3-triazol-1-yl 662 Me CH2(4-Me Ph) 2-CF3 1,2,3-triazol-2-yl 663 Me CH2(4-Me Ph) 2-CH2SMe 1,2,3-triazol-2-yl 664 Me CH2(4-Me Ph) 2-Cl 1,2,3-triazol-2-yl 665 Me CH2(4-Me Ph) 2-Me 1,2,3-triazol-2-yl 666 Me CH2(4-Me Ph) 2-SMe 1,2,3-triazol-2-yl 667 Me CH2(4-Me Ph) 2-SMe-3-Br 1 ,2,3-triazol-2-yl 668 Me CH2(4-Me Ph) 2-SMe-3-F 1,2,3-triazol-2-yl 669 Me CH2(4-Me Ph) 2-SMe-3-SMe 1 ,2,3-triazol-2-yl 670 Me CH2(4-Me Ph) 2-Br 1,2,4-triazol-l-yl 671 Me CH2(4-Me Ph) 2-CH2[(2-MeS)Ph] 1,2,4-triazol-1-yl 672 Me CH2(4-Me Ph) 2-CH2[(2-MeSO)Phl 1,2,4-triazol-1-yl 673 Me CH2(4-Me Ph) 2-CH2[(2-MeSO2)Ph] 1,2,4-triazol-1-yl 674 Me CH2(4-Me Ph) 2-CH2N(Me)CO2Me 1 ,2,4-triazol- 1 -yl 675 Me CH2(4-Me Ph) 2-CH2N(Me)SO2Me 1,2,4-triazol-l-yl 676 Me CH2(4-Me Ph) 2-CH2Ph 1,2,4-triazol-1-yl 677 Et CH2CO(4-Me Ph) 2-CH2SMe 1,2,4-triazol-1-yl 678 Et CH2(4-Me Ph) 2-CH2SMe 1,2,4-triazol-1-yl 679 Me CH2(4-Me Ph) 2-CH2SO2Me 1,2,4-triazol-1-yl 680 Et CH2(4-Me Ph) 2-CH2SMe 1,2,4-triazol-1-yl 681 Me CH2(4-Me Ph) 2-Cl 1,2,4-triazol-1-yl 682 Me CH2(4-Me Ph) 2-Me 1,2,4-triazol-l-yl 683 Me CH2(4-Me Ph) 2-Me-3-SMe 1,2,4-triazol-1-yl 684 Me CH2(4-Me Ph) 2-Me-3-SO2Me 1,2,4-triazol-1-yl 685 Me CH2(4-Me Ph) 2-Me-3-SOMe 1,2,4-triazol-1-yl 686 Me CH2(4-Me Ph) 2-NMeCO2Me 1,2,4-triazol-1-yl 687 Me CH2(4-Me Ph) 2-NMeSO2Me 1,2,4-triazol-1-yl 688 Me CH2(4-Me Ph) 2-OMe 1,2,4-triazol-1-yl 689 Me CH2(4-Me Ph) 2-OMe-3-SMe 1,2,4-triazol-l-yl 690 Me CH2(4-Me Ph) 2-OMe-3-SO2Me 1,2,4-triazol-1-yl 691 Me CH2(4-Me Ph) 2-OMe-3-SOMe 1,2,4-triazol-l-yl 692 Me CH2(4-Me Ph) 2-SMe 1 ,2,4-triazol- 1 -yl 693 Me CH2(4-Me Ph) 2-SMe-3-Br 1,2,4-triæol-1-yl 694 Me CH2(4-Me Ph) 2-SMe-3-Cl 1,2,4-triazol-1-yl 695 Me CH2(4-Me Ph) 2-SMe-3-F 1,2,4-triazol-1-yl 696 Me CH2(4-Me Ph) 2-SMe-3-OMe 1,2,4-triazol-l-yl Cpd Rb Q (R2)n (XR3)z No. 697 Me CH2(4-Me Ph) 2-SMe-3-SMe 1,2,4-triazol-1-yl 698 Me CH2(4-Me Ph) 2-SO2Me 1,2,4-triazol-1-yl 699 Me CH2(4-Me Ph) 2-SO2Me-3-CI 1,2,4-triazol-1-yl 700 Me CH2(4-Me Ph) 2-SO2Me-3-OMe 1,2,4-triazol-1-yl 701 Me CH2(4-Me Ph) 2-SOMe 1,2,4-triazol-1-yl 702 Me CH2(4-Me Ph) 2-SOMe-3-Cl 1,2,4-triazol-1-yl 703 Me CH2(4-Me Ph) 2-SOMe-3-OMe 1,2,4-triazol-1-yl 704 Me CH2(4-Me Ph) 2-NO2 1,2,4-triazol-1-yl 705 Me CH2(4-Me Ph) 2-CF3 imidazol-1-yl 706 Me CH2(4-Me Ph) 2-CH2SMe imidazol-l-yl 707 Me Ch2(4-Me Ph) 2-Cl imidazol-1-yl 708 Me CH2(4-Me Ph) 2-Me imidazol-1-yl 709 Me CH2(4-Me Ph) 2-SMe imidazol-1-yl 710 Me CH2(4-Me Ph) 2-SMe-3-Br imidazol-1-yl 711 Me CH2(4-Me Ph) 2-SMe-3-F imidazol-1-yl 712 Me CH2(4-Me Ph) 2-SMe-3-SMe imidazol-1-yl 713 Me CH2(4-Me Ph) 2-CF3 pyrazol-1-yl 714 Me CH2(4-Me Ph) 2-CH2SMe pyrazol-1-yl 715 Me CH2(4-Me Ph) 2-Cl pyrazol-1-yl 716 Me CH2(4-Me Ph) 2-Me pyrazo1- 1 -y1 717 Me CH2(4-Me Ph) 2-SMe pyrazol-1-yl 718 Me CH2(4-Me Ph) 2-CF3 tetrazol- 1 -yl 719 Me CH2(4-Me Ph) 2-SMe tetrazol-l-yl 720 Me CH2(4-Me Ph) 2-SMe-3-SMe tetrazol-l-yl 721 Me S02(4-Me Ph) 2-CF3 3-Me- 1 ,2,4-triazol- 1 -yl 722 Me CH2CO(4-Me Ph) 2-CF3 3-Me-1,2,4-triazol-1-yl 723 Me CH2(4-Me Ph) 2-CF3 3-Me-1,2,4-triazol-1-yl 724 Me SO2(4-Me Ph) 2-CF3 CH2(1,2,4-triazol-1-yl) 725 Me CH2CO(4-Me Ph) 2-CF3 CH2(1,2,4-triazol-1-yl) 1114 Me CH2CO(4-Me Ph) 2-Cl-3-Me 1 ,2,4-triazol- 1 -yl 1115 Me SO2(4-Me Ph) 2-Cl-3-Me 1,2,4-triazol-1-yl 1116 Me H 2-Cl 1,2,4-triazol-1-yl 1117 H COPh 2-CF3 1,2,4-triazol-1-yl 1118 H COtBu 2-CF3 1,2,4-triazol-1-yl 1119 H SO2Ph 2-CF3 1,2,4-triazol-1-yl 1120 H 502(4-Me Ph) 2-CF3 1,2,4-triazol-1-yl 1121 Me COMe 2-Cl 1,2,4-triazol-1-yl 1122 Me COtBu 2-Cl 1,2,4-triazol-1-yl 1123 Me SO2Ph 2-Cl 1,2,4-triazol-1-yl 1124 Me SO2iPr 2-Cl 1,2,4-triazol-1-yl 1125 Me Me 2-Cl 1,2,4-triazol-1-yl Cpd Rb Q (R2)n (XR3)z No. 1126 Me CH2COPh 2-Cl 1,2,4-triazol-1-yl 1127 Me CH2Ph 2-Cl 1,2,4-triazol-1-yl 1128 Me prop-2-ynyl 2-Cl 1,2,4-triazol-l-yl 1129 Me CH2CH=CH2 2-Cl 1 ,2,4-triazol- 1 -yl 1130 H COMe 2-CF3 1,2,4-triazol-1-yl 1131 H CH2Ph 2-CF3 1,2,4-triazol-1-yl 1132 H CH2CH=CH2 2-CF3 1,2,4-triazol-l-yl 1133 Me H 2-Br 1,2,4-triazol-1-yl 1134 H H 2-Br 1 *2,4-triazol-1 -yl 1135 H H 2-F 1,2,4-triazol-1-yl 1136 H H 2-Cl 1,2,4-triazol-l-yl 1137 H H 2-SMe 1,2,4-triazol-l-yl 1138 H H 2-SOMe 1,2,4-triazol-1-yl 1139 H H 2-SO2Me 1,2,4-triazol-1-yl 1140 H H 2-Me 1,2,4-triazol-1-yl 1141 Me H 2-F 1,2,4-triazol-1-yl 1142 Me H 2-SMe 1,2,4-triazol-1-yl 1143 Me H 2-SOMe 1,2,4-triazol-1-yl 1144 Me H 2-SO2Me 1 ,2,4-triazol- 1 -yl 1145 Me H 2-Me 1,2,4-triazol-1-yl 1146 cPr H 2-F 1,2,4-triazol-1-yl 1147 cPr H 2-Cl 1,2,4-triazol-1-yl 1148 cPr H 2-Br 1,2,4-triazol-1-yl 1149 cPr H 2-SMe 1 ,2,4-triazol- 1 -yl 1150 cPr H 2-SOMe 1,2,4-triazol-1-yl 1151 cPr H 2-SO2Me 1,2,4-triazol-1-yl 1152 cPr H 2-Me 1 ,2,4-triazol- 1 -yl 1153 cPr S02(4-Me Ph) 2-CF3 1,2,4-triazol-1-yl 1154 cPr CH2CO(4-Me Ph) 2-CF3 1 ,2,4-triazol- 1 -yl 1155 cPr CH2(4-Me Ph) 2-CF3 1,2,4-triazol-1-yl 1156 cPr H 2-CF3 1,2,4-triazol-l-yl TABLE 7 Cpd Rb Q (R2)n (XR3)z No. 726 Me SO2(4-Me Ph) 4-Br 1,2,3-triazol-1-yl 727 Me SO2(4-Me Ph) 4-CF3 1,2,3-triazol-1-yl 728 Me SO2(4-Me Ph) 4-Cl 1,2,3-triazol-1-yl 729 Me S02(4Me Ph) 4-F 1,2,3 triazol-1-yl 730 Me SO2(4-Me Ph) 4-SMe 1,2,3-triazol-1-yl Cpd Rb Q (R2)n (XR3)z No. 731 Me SO2(4-Me Ph) 4-Br 1,2,3-triazol-2-yl 732 Me 502(4-Me Pb) 4-CF3 1,2,3-triazol-2-yl 733 Me 502(4-Me Ph) 4-Cl 1,2,3-triazol-2-yl 734 Me S02(4-Me Ph) 4-F 1,2,3-triazol-2-yl 735 Me SO2(4-Me Ph) 4-SMe 1,2,3-triazol-2-yl 736 Me SO2(4-Me Ph) 3,4-C12 1,2,4-triazol-1-yl 737 Me SO2(4-Me Ph) 3,4-F2 1,2,4-triazol-1-yl 738 Me SO2(4-Me Ph) 3-Br 1,2,4-triazol-l-yl 739 Me SO2(4-Me Ph) 3-CF3 1,2,4-triazol-1-yl 740 Me SO2(4-Me Ph) 3-CH2SO2Me 1,2,4-triazol-1-yl 741 Me CH2CO(4-Me Ph) 3-CH2SO2Me 1,2,4-triazol-1-yl 742 Me SO2(4-Me Ph) 3-CH2SOMe 1,2,4-triazol-1-yl 743 Me SO2(4-Me Ph) 3-Cl 1,2,4-triazol-1-yl 744 Me SO2(4-Me Ph) 3-F 1,2,4-triazol-1-yl 745 Me SO2(4-Me Ph) 3-Me 1,2,4-triazol-1-yl 746 Me SO2(4-Me Ph) 3-Me-4-F 1,2,4-triazol-1-yl 747 Me SO2(4-Me Ph) 3-Me-4-SMe 1,2,4-triazol-1-yl 748 Me SO2(4-Me Ph) 3-OMe 1,2,4-triazol-1-yl 749 Me SO2(4-Me Ph) 3-SMe 1,2,4-triazol-1-yl 750 Me SO2(4-Me Ph) 3-SMe-4-F 1,2,4-triazol-1-yl 751 Me SO2(4-Me Ph) 3-SMe-4-OMe 1,2,4-triazol-1-yl 752 Me SO2(4-Me Ph) 3-SMe-4-SMe 1,2,4-triazol-1-yl 753 Me SO2(4-Me Ph) 3-SO2Me 1,2,4-triazol-1-yl 754 Me SO2(4-Me Ph) 3-SO2Me-4-F 1,2,4-triazol-1-yl 755 Me SO2(4-Me Ph) 3-SO2Me-4-OMe 1,2,4-triazol-1-yl 756 Me SO2(4-Me Ph) 3-SO2Me-4-SO2Me 1,2,4-triazol-1-yl 757 Me SO2(4-Me Ph) 3-SOMe 1,2,4-triazol-1-yl 758 Me SO2(4-Me Ph) 3-SOMe-4-F 1,2,4-triazol-1-yl 759 Me SO2(4-Me Ph) 3-SOMe-4-OMe 1,2,4-triazol-1-yl 760 Me SO2(4-Me Ph) 4-Br 1,2,4-triazol-1-yl 761 Me H 4-CF3 1,2,4-triazol-1-yl 762 Me CH2COPh 4-CF3 1,2,4-triazol-I-yl 763 Me Me 4-CF3 1,2,4-triazol-1-yl 764 Me Et 4-CF3 1 ,2,4-triazol- 1 -yl 765 Me iPr 4-CF3 1,2,4-triazol-1-yl 766 Me CH2Ph 4-CF3 1,2,4-triazol-1-yl 767 Me CH2CO2Me 4-CF3 1,2,4-triazol-1-yl 768 Me CH(CO2Me)Me 4-CF3 1,2,4-triazol-1-yl 769 Me CH2CH=CH2 4-CF3 1 ,2,4-triazol- 1 -yl 770 Me prop-2-ynyl 4-CF3 1,2,4-triazol-1-yl 771 Me SO2Ph 4-CF3 1,2,4-triazol-1-yl Cpd Rb Q (R2)n (XR3)z No. 772 Me COMe 4-CF3 1 ,2,4-triazol- 1 -yl 773 Me COtBu 4-CF3 1,2,4-triazol-1-yl 774 Me SO2(4-Me Ph) 4-CF3 1 ,2,4-triazol- 1 -yl 775 Me S02iPr 4-CF3 1 ,2,4-triazol- 1 -yl 776 Me CH2CO(4-Me Ph) 4-CF3 1,2,4-triazol-1-yl 777 H SO2(4-Me Ph) 4-CF3 1,2,4-triazol-l-yl 778 H H 4-CF3 1,2,4-triazol-1-yl 779 Me SO2(4-Me Ph) 4-Cl 1,2,4-triazol-1-yl 780 Me SO2(4-Me Ph) 4-F 1,2,4-triazol-1-yl 781 Me SO2(4-Me Ph) 4-Me 1,2,4-triazol-l-yl 782 Me SO2(4-Me Ph) 4-OMe 1,2,4-triazol-1-yl 783 Me SO2(4-Me Ph) 4-SMe 1,2,4-triazol-1-yl 784 Me SO2(4-Me Ph) 4-SO2Me 1,2,4-triazol-l-yl 785 Me S02(4-Me Ph) 4-SOMe 1 ,2,4-triazol- 1 -yl 786 Me SO2(4-Me Ph) - 1,2,4-triazol-l-yl 787 Me SO2(4-Me Ph) 4-Br imidazol-l-yl 788 Me SO2(4-Me Ph) 4-CF3 imidazol-l-yl 789 Me SO2(4-Me Ph) 4-Cl imidazol-1-yl 790 Me SO2(4-Me Ph) 4-F imidazol-l-yl 791 Me SO2(4-Me Ph) 4-SMe imidazol-1-yl 792 Me SO2(4-Me Ph) - pyrazol-l-yl 793 Me SO2(4-Me Ph) 4-Br tetrazol-1-yl 794 Me SO2(4-Me Ph) 4-CF3 tetrazol-1-yl 795 Me SO2(4-Me Ph) 4-Cl tetrazol-1-yl 796 Me SO2(4-Me Ph) 4-F tetrazol-1-yl 797 Me S02(4-Me Ph) 4-SMe tetrazol-l-yl 798 Me SO2(4-Me Ph) 4-Br benzimidazol-1-yl 799 Me SO2(4-Me Ph) 4-CF3 benzimidazol-1-yl 800 Me SO2(4-Me Ph) 4-Cl benzimidazol-1-yl 801 Me SO2(4-Me Ph) 4-F benzimidazol-1-yl 802 Me SO2(4-Me Ph) 4-SMe benzimidazol-l-yl 803 Me CH2CO(4-Me Ph) 4-Br 1,2,3-triazol-l-yl 804 Me CH2CO(4-Me Ph) 4-CF3 1,2,3-triazol-l-yl 805 Me CH2CO(4-Me Ph) 4-Cl 1,2,3-triazol-1-yl 806 Me CH2CO(4-Me Ph) 4-F 1,2,3-triazol-1-yl 807 Me CH2CO(4-Me Ph) 4-SMe 1,2,3-triazol-1-yl 808 Me CH2CO(4-Me Ph) 4-Br 1,2,3-triazol-2-yl 809 Me CH2CO(4-Me Ph) 4-CF3 1,2,3-triazol-2-yl 810 Me CH2CO(4-Me Ph) 4-Cl 1,2,3-triazol-2-yl 811 Me CH2CO(4-Me Ph) 4-F 1,2,3-triazol-2-yl 812 Me CH2CO(4-Me Ph) 4-SMe 1,2,3-triazol-2-yl Cpd Rb Q (R2)n (XR3)z No. 813 Me CH2CO(4-Me Ph) 3,4-Cl2 1,2,4-triazol-1-yl 814 Me CH2CO(4-Me Ph) 3,4-F2 1,2,4-triazol-1-yl 815 Me CH2CO(4-Me Ph) 3-Br 1,2,4-triazol-1-yl 816 Me CH2CO(4-Me Ph) 3-CF3 1 ,2,4-triazol- 1 -y1 817 Me CH2(4-Me Ph) 3-CH2SO2Me 1,2,4-triazol-1-yl 818 H SO2(4-Me Ph) 3-CH2SO2Me 1,2,4-triazol-1-yl 819 Me CH2CO(4-Me Ph) 3-CH2SOMe 1,2,4-triazol-1-yl 820 Me CH2CO(4-Me Ph) 3-Cl 1,2,4-triazol-1-yl 821 Me CH2CO(4-Me Ph) 3-F 1,2,4-triazol-1-yl 822 Me CH2CO(4-Me Ph) 3-Me 1,2,4-triazol-1-yl 823 Me CH2CO(4-Me Ph) 3-Me-4-F 1,2,4-triazol-1-yl 824 Me CH2CO(4-Me Ph) 3-Me-4-SMe 1,2,4-triazol-1-yl 825 Me CH2CO(4-Me Ph) 3-OMe 1,2,4-triazol-1-yl 826 Me CH2CO(4-Me Ph) 3-SMe 1,2,4-triazol-1-yl 827 Me CH2CO(4-Me Ph) 3-SMe-4-F 1,2,4-triazol-1-yl 828 Me CH2CO(4-Me Ph) 3-SMe-4-OMe 1,2,4-triazol-1-yl 829 Me CH2CO(4-Me Ph) 3-SMe-4-SMe 1,2,4-triazol-1-yl 830 Me CH2CO(4-Me Ph) 3-SO2Me 1,2,4-triazol-1-yl 831 Me CH2CO(4-Me Ph) 3-SO2Me-4-F 1 ,2,4-triazol- 1 -yl 832 Me CH2CO(4-Me Ph) 3-SO2Me-4-OMe 1 ,2,4-triazol-1-yl 833 Me CH2CO(4-Me Ph) 3-SO2Me-4-SO2Me 1,2,4-triazol-1-yl 834 Me CH2CO(4-Me Ph) 3-SOMe 1,2,4-triazol-1-yl 835 Me CH2CO(4-Me Ph) 3-SOMe-4-F 1,2,4-triazol-1-yl 836 Me CH2CO(4-Me Ph) 3-SOMe-4-OMe 1,2,4-triazol-l-yl 837 Me CH2CO(4-Me Ph) 4-Br 1,2,4-triazol-1-yl 838 H CH2CO(4-Me Ph) 4-CF3 1,2,4-triazol-1-yl 839 Me CH2CO(4-Me Ph) 4-Cl 1,2,4-triazol-1-yl 840 Me CH2CO(4-Me Ph) 4-F 1,2,4-triazol-l-yl 841 Me CH2CO(4-Me Ph) 4-Me 1,2,4-triazol-1-yl 842 Me CH2CO(4-Me Ph) 4-OMe 1,2,4-triazol-1-yl 843 Me CH2CO(4-Me Ph) 4-SMe 1,2,4-triazol-l-yl 844 Me CH2CO(4-Me Ph) 4-SO2Me 1,2,4-triazol-l-yl 845 Me CH2CO(4-Me Ph) 4-SOMe 1 ,2,4-triazol- 1 -y1 846 Me CH2CO(4-Me Ph) - 1,2,4-triazol-1-yl 847 Me CH2CO(4-Me Ph) 4-Br imidazol-1-yl 848 Me CH2CO(4-Me Ph) 4-CF3 imidazol-1-yl 849 Me CH2CO(4-Me Ph) 4-Cl imidazol-1-yl 850 Me CH2CO(4-Me Ph) 4-F imidazol-1-yl 851 Me CH2CO(4-Me Ph) 4-SMe imidazol- 1 -yl 852 Me CH2CO(4-Me Ph) - pyrazol-1-yl 853 Me CH2CO(4-Me Ph) 4-Br tetrazol-1-yl Cpd Rb Q (R2)n (XR3)z No. 854 Me CH2CO(4-Me Ph) 4-CF3 tetrazol-l-yl 855 Me C.H2CO(4-Me Pb) 4-Cl tetrazol-l-yl 856 Me CH2CO(4-Me Ph) 4-F tetrazol-1-yl 857 Me CH2CO(4-Me Pb) 4-SMe tetrazol-1-yl 858 Me CH2CO(4-Me Ph) 4-Br benzimidazol-l-yl 859 Me CH2CO(4-Me Ph) 4-CF3 benzimidazol-1-yl 860 Me CH2CO(4-Me Ph) 4-Cl benzimidazol-l-yl 861 Me CH2CO(4-Me Ph) 4-F benzimidazol-l-yl 862 Me CH2CO(4-Me Ph) 4-SMe benzimidazol-l-yl 863 Me CH2(4-Me Ph) 4-Br 1,2,3-triazol-1-yl 864 Me CH2(4-Me Ph) 4-CF3 1,2,3-triazol-1-yl 865 Me CH2(4-Me Ph) 4-Cl 1,2,3-triazol-1-yl 866 Me CH2(4-Me Ph) 4-F 1,2,3-triazol-1-yl 867 Me CH2(4-Me Ph) 4-SMe 1,2,3-triazol-1-yl 868 Me CH2(4-Me Ph) 4-Br l,2,3-triazol-2-yl 869 Me CH2(4-Me Ph) 4-CF3 1,2,3-triazol-2-yl 870 Me CH2(4-Me Ph) 4-Cl 1,2,3-triazol-2-yl 871 Me CH2(4-Me Ph) 4-F 1,2,3-triazol-2-yl 872 Me CH2(4-Me Ph) 4-SMe 1,2,3-triazol-2-yl 873 Me CH2(4-Me Ph) 3,4-C12 1,2,4-triazol-1-yl 874 Me CH2(4-Me Ph) 3,4-F2 1,2,4-triazol-l-yl 875 Me CH2(4-Me Ph) 3-Br 1,2,4-triazol-1-yl 876 Me CH2(4-Me Ph) 3-CF3 1,2,4-triazol-1-yl 877 H CH2CO(4-Me Ph) 3-CH2SO2Me 1,2,4-triazol-1-yl 878 H CH2(4-Me Ph) 3-CH2SO2Me 1,2,4-triazol-1-yl 879 Me CH2(4-Me Ph) 3-CH2SOMe 1,2,4-triazol-1-yl 880 Me CH2(4-Me Ph) 3-Cl 1,2,4-triazol-1-yl 881 Me CH2(4-Me Ph) 3-F 1,2,4-triazol-1-yl 882 Me CH2(4-Me Ph) 3-Me 1,2,4-triazol-1-yl 883 Me CH2(4-Me Ph) 3-Me-4-F 1,2,4-triazol-1-yl 884 Me CH2(4-Me Ph) 3-Me-4-SMe 1,2,4-triazol-1-yl 885 Me CH2(4-Me Ph) 3-OMe 1,2,4-triazol-1-yl 886 Me CH2(4-Me Ph) 3-SMe 1,2,4-triazol-1-yl 887 Me CH2(4-Me Ph) 3-SMe-4-F 1,2,4-triazol-1-yl 888 Me CH2(4-Me Ph) 3-SMe-4-OMe 1,2,4-triazol-1-yl 889 Me CH2(4-Me Ph) 3-SMe-4-SMe 1,2,4-triazol-l-yl 890 Me CH2(4-Me Ph) 3-SO2Me 1,2,4-triazol-1-yl 891 Me CH2(4-Me Ph) 3-SO2Me-4-F 1,2,4-triazol-1-yl 892 Me CH2(4-Me Ph) 3-SO2Me-4-OMe 1,2,4-triazol-1-yl 893 Me CH2(4-Me Ph) 3-SO2Me-4-SO2Me 1,2,4-triazol-1-yl 894 Me CH2(4-Me Ph) 3-SOMe 1,2,4-triæol-1-yl Cpd Rb Q (R2)n (XR3)z No. 895 Me CH2(4-Me Ph) 3-SOMe-4-F 1,2,4-triazol-1-yl 896 Me CH2(4-Me Ph) 3-SOMe-4-OMe 1,2,4-triazol-1-yl 897 Me CH2(4-Me Ph) 4-Br 1,2,4-triazol-1-yl 898 Me CH2(4-Me Ph) 4-CF3 1 ,2,4-triazol- 1 -yl 899 Me CH2(4-Me Ph) 4-Cl 1,2,4-triazol-1-yl 900 Me CH2(4-Me Ph) 4-F 1 ,2,4-triazol- 1 -yl 901 Me CH2(4-Me Ph) 4-Me 1,2,4-triazol-1-yl 902 Me CH2(4-Me Ph) 4-OMe 1,2,4-triazol-1-yl 903 Me CH2(4-Me Ph) 4-SMe 1,2,4-triazol-1-yl 904 Me CH2(4-Me Ph) 4-SO2Me 1,2,4-triazol-1-yl 905 Me CH2(4-Me Ph) 4-SOMe 1,2,4-triazol-1-yl 906 Me CH2(4-Me Ph) - 1,2,4-triazol-1-yl 907 Me CH2(4-Me Ph) 4-Br imidazol-l-yl 908 Me CH2(4-Me Ph) 4-CF3 imidazol-l-yl 909 Me CH2(4-Me Ph) 4-Cl imidazol-l-yl 910 Me CH2(4-Me Ph) 4-F imidazol- 1 -yl 911 Me CH2(4-Me Ph) 4-SMe imidazol-l-yl 912 Me CH2(4-Me Ph) - pyrazol-1-yl 913 Me CH2(4-Me Ph) 4-Br tetrazol- 1 -yl 914 Me CH2(4-Me Ph) 4-CF3 tetrazol-1-yl 915 Me CH2(4-Me Ph) 4-Cl tetrazol- 1 -yl 916 Me CH2(4-Me Ph) 4-F tetrazol- 1 -yl 917 Me CH2(4-Me Ph) 4-SMe tetrazol-1-yl 918 Me CH2(4-Me Ph) 4-Br benzimidazol-1-yl 919 Me CH2(4-Me Ph) 4-CF3 benzimidazol-1-yl 920 Me CH2(4-Me Ph) 4-Cl benzimidazol-l-yl 921 Me CH2(4-Me Ph) 4-F benzimidazol- 1 -yl 922 Me CH2(4-Me Ph) 4-SMe benzimidazol-1-yl 923 Me SO2(4-Me Ph) 4-Br CH2-(triazol-1-yl) 924 Me SO2(4-Me Ph) 4-Cl CH2-(triazol-1-yl) 925 Me SO2(4-Me Ph) 4-F CH2-(triazol-1-yl) 926 Me SO2(4-Me Ph) 4-CF3 CH2-(triazol-1-yl) 927 Me SO2(4-Me Ph) 4-OF3 CH2-(triazol-1-yl) 928 Me SO2(4-Me Ph) 4-Me CH2-(triazol-1-yl) 1157 Me H 4-F 1,2,4-triazol-1-yl 1158 Me H 4-Cl 1,2,4-triazol-1-yl 1159 Me H 4-Br 1,2,4-triazol-1-yl 1160 Me H 4-SMe 1,2,4-triazol-1-yl 1161 Me H 4-SOMe 1,2,4-triazol-1-yl 1162 Me H 4-SO2Me 1,2,4-triazol-1-yl 1163 Me H 4-Me 1,2,4-triazol-1-yl Cpd Rb Q (R2)n (XR3)z No. 772 Me COMe 4-CF3 I ,2,4-triazol- 1 -yl 773 Me COtBu 4-CF3 1,2,4-triazol-1-yl 774 Me SO2-(4-Me Ph) 4-CF3 1 ,2,4-triazol- 1 -y1 775 Me S02iPr 4-CF3 1,2,4-triazol-1-yl 776 Me CH2C0(4-Me Ph) 4-CF3 1,2,4-triazol-1-yl 777 H 502(4-Me Ph) 4-CF3 1,2,4-triazol-1-yl 778 H H 4-CF3 1,2,4-triazol-l-yl 779 Me SO2(4-Me Ph) 4-Cl 1,2,4-triazol-1-yl 780 Me SO2(4-Me Ph) 4-F 1,2,4-triazol-1-yl 781 Me SO2(4-Me Ph) 4-Me 1 ,2,4-triazol-1 -y1 782 Me SO2-(4-Me Ph) 4-OMe 1,2,4-triazol-1-yl 783 Me SO2-(4-Me Ph) 4-SMe 1,2,4-triazol-l-yl 784 Me SO2(4-Me Ph) 4-SO2Me 1,2,4-triazol-1-yl 785 Me SO2(4-Me Ph) 4-SOMe 1,2,4-triazol-1-yl 786 Me SO2(4-Me Ph) - 1,2,4-triazol-1-yl 787 Me SO2(4-Me Ph) 4-Br imidazol-1-yl 788 Me SO2(4-Me Ph) 4-CF3 imidazol-1-yl 789 Me SO2(4-Me Ph) 4-Cl imidazol-1-yl 790 Me 502(4-Me Ph) 4-F imidazol-l-yl 791 Me SO2(4-Me Ph) 4-SMe imidazol-1-yl 792 Me 502(4-Me Ph) - pyrazol-l-yl 793 Me SO2(4-Me Ph) 4-Br tetrazol-1-yl 794 Me SO2(4-Me Ph) 4-CF3 tetrazol-1-yl 795 Me SO2(4-Me Ph) 4-Cl tetrazol-1-yl 796 Me SO2(4-Me Ph) 4-F tetrazol-1-yl 797 Me S02(4-Me Ph) 4-SMe tetrazol-1-yl 798 Me SO2(4-Me Ph) 4-Br benzimidazol-1-yl 799 Me 502(4-Me Ph) 4-CF3 benzimidazol-l-yl 800 Me SO2(4-Me Ph) 4-Cl benzimidazol-1-yl 801 Me SO2(4-Me Ph) 4-F benzimidazol-1-yl 802 Me SO2(4-Me Ph) 4-SMe benzimidazol-1-yl 803 Me CH2CO(4-Me Ph) 4-Br 1,2,3-triazol-l-yl 804 Me CH2CO(4-Me Ph) 4-CF3 1,2,3-triazol-1-yl 805 Me CH2CO(4-Me Ph) 4-Cl 1,2,3-triazol-l-yl 806 Me CH2CO(4-Me Ph) 4-F 1,2,3-trazol-1-yl 807 Me CH2CO(4-Me Ph) 4-SMe 1,2,3-triazol-l-yl 808 Me CH2CO(4-Me-Ph) 4-Br 1,2,3-triazol-2-yl 809 Me CH2CO(4-Me-Ph) 4-CF3 1,2,3-triazol-2-yl 810 Me CH2CO(4-Me-Ph) 4-Cl 1,2,3-triazol-2-yl 811 Me CH2CO(4-Me Ph) 4-F 1,2,3-triazol-2-yl 812 Me CH2CO(4-Me Ph) 4-SMe 1,2,3-triazol-2-yl Cpd Rb Q (R2)n (XR3)z No. 941 Me SO2(4-Me Ph) 2-SO2Me-4-SO2Me 1,2,3-triazol-1-yl 942 Me SO2(4-Me Ph) 2-SO2Me 1,2,3-triazol-1-yl 943 Me SO2(4-Me Ph) 2-Br 1,2,4-triazol-1-yl 944 Me H 2-CF3 1 ,2,4-triazol- 1 -yl 945 Me CH2COPh 2-CF3 1 ,2,4-triazol- 1 -yl 946 Me Me 2-CF3 1 ,2,4-triazol- 1 -yl 947 Me Et 2-CF3 1,2,4-triazol-1-yl 948 Me iPr 2-CF3 1,2,4-triazol-1-yl 949 Me CH2Ph 2-CF3 1 ,2,4-triazol- 1 -yl 950 Me CH2CO2Me 2-CF3 1,2,4-triazol-1-yl 951 Me CH(CO2Me)Me 2-CF3 1,2,4-triazol-1-yl 952 Me CH2CH=CH2 2-CF3 1,2,4-triazol-1-yl 953 Me prop-2-ynyl 2-CF3 1,2,4-triazol-1-yl 954 Me SO2Ph 2-CF3 1,2,4-triazol-1-yl 955 Me COMe 2-CF3 1,2,4-triaozl-1-yl 956 Me COPh 2-CF3 1,2,4-triazol-1-yl 957 Me COtBu 2-CF3 1,2,4-triazol-1-yl 958 Me SO2(4-Me Ph) 2-CF3 1,2,4-triazol-1-yl 959 Me SO2iPr 2-CF3 1 ,2,4-triazol- 1 -yl 960 Me CH2(4-Me Ph) 2-CF3 1 ,2,4-triazol- 1 -yl 961 Me CH2CO(4-Me Ph) 2-CF3 1,2,4-triazol-1-yl 962 Me S02(4-Me Ph) 2-CH2SMe 1,2,4-triazol-1-yl 963 Me SO2(4-Me Ph) 2-Cl 1,2,4-triazol-1-yl 964 Me S02(4-Me Ph) 2-F 1 ,2,4-triazol- 1 -yl 965 Me SO2(4-Me Ph) 2-SMe 1,2,4-triazol-1-yl 966 Me SO2(4-Me Ph0 2-SMe-4-Br 1,2,4-triazol-1-yl 967 Me S02(4-Me Ph) 2-SMe-4-CF3 1,2,4-triazol-l-yl 968 Me SO2(4-Me Ph) 2-SMe-4-Cl 1,2,4-triazol-1-yl 969 Me SO2(4-Me Ph) 2-SMe-4-F 1,2,4-triazol-1-yl 970 Me SO2(4-Me Ph) 2-SMe-4-SMe 1,2,4-triazol-1-yl 971 Me SO2(4-Me Ph) 2-SO2Me 1,2,4-triazol-1-yl 972 Me SO2(4-Me Ph) 2-SO2Me-4-SO2Me 1,2,4-triazol-1-yl 973 Me SO2(4-Me Ph) 2-SO2Me 1,2,4-triazol-1-yl 974 Me SO2(4-Me Ph) 2-Br imidazol-1-yl 975 Me SO2(4-Me Ph) 2-CF3 imidazol-1-yl 976 Me SO2(4-Me Ph) 2-CH2SMe imidazol-1-yl 977 Me SO2(4-Me Ph) 2-Cl imidazol-1-yl 978 Me SO2(4-Me Ph) 2-F imidazol-1-yl 979 Me SO2(4-Me Ph) 2-SMe imidazol-1-yl 980 Me SO2(4-Me Ph) 2-SMe-4-Br imidazol-1-yl 981 Me SO2(4-Me Ph) 2-SMe-4-CF3 imidazol-1-yl Cpd Rb Q (R2)n (XR3)z No. 982 Me SO2(4-Me Ph) 2-SMe-4-Cl imidazol-l-yl 983 Me S02(4-Me Ph) 2-SMe-4-F imidazol-1-yl 984 Me SO2(4-Me Ph) 2-SMe-4-SMe imidazol-1-yl 985 Me S02(4-Me Ph) 2-SO2Me imidazol-1-yl 986 Me SO2(4-Me Ph) 2-SO2Me-4-SO2Me imidazol-1-yl 987 Me SO2(4-Me Ph) 2-SO2Me imidazol-1-yl 988 Me SO2(4-Me Ph) 2-Br tetrazol-1-yl 989 Me SO2(4-Me Ph) 2-CF3 tetrazol-1-yl 990 Me SO2(4-Me Ph) 2-CH2SMe tetrazol-1-yl 991 Me SO2(4-Me Ph) 2-Cl tetrazol-1-yl 992 Me SO2(4-Me Ph) 2-F tetrazol-1-yl 993 Me SO2(4-Me Ph) 2-SMe tetrazol-1-yl 994 Me SO2(4-Me Ph) 2-SMe-4-Br tetrazol-1-yl 995 Me SO2(4-Me Ph) 2-SMe-4-CF3 tetrazol-1-yl 996 Me SO2(4-Me Ph) 2-SMe-4-Cl tetrazol-1-yl 997 Me SO2(4-Me Ph) 2-SMe-4-F tetrazol-l-yl 998 Me SO2(4-Me Ph) 2-SMe-4-SMe tetrazol-1-yl 999 Me SO2(4-Me Ph) 2-SO2Me tetrazol-1-yl 1000 Me SO2(4-Me Ph) 2-SO2Me-4-SO2Me tetrazol-1-yl 1001 Me SO2(4-Me Ph) 2-SO2Me tetrazol-1-yl 1002 Me CH2CO(4-Me Ph) 2-Br 1,2,3-triazol-1-yl 1003 Me CH2CO(4-Me Ph) 2-CF3 1,2,3-triazol-1-yl 1004 Me CH2CO(4-Me Ph) 2-CH2SMe 1,2,3-triazol-1-yl 1005 Me CH2CO(4-Me Ph) 2-Cl 1,2,3-triazol-1-yl 1006 Me CH2CO(4-Me Ph) 2-F 1,2,3-triazol-1-yl 1007 Me CH2CO(4-Me Ph) 2-SMe 1,2,3-triazol- 1 -yl 1008 Me CH2CO(4-Me Ph) 2-SMe-4-Br 1,2,3-triazol-1-yl 1009 Me CH2CO(4-Me Ph) 2-SMe-4-CF3 1,2,3-triazol-1-yl 1010 Me CH2CO(4-Me Ph) 2-SMe-4-Cl 1,2,3-triazol-1-yl 1011 Me CH2CO(4-Me Ph) 2-SMe-4-F 1 ,2,3-triazol- 1-yl 1012 Me CH2CO(4-Me Ph) 2-SMe-4-SMe 1,2,3-triazol-l-yl 1013 Me CH2CO(4-Me Ph) 2-SO2Me 1,2,3-triazol-1-yl 1014 Me CH2CO(4-Me Ph) 2-SO2Me-4-SO2Me 1,2,3-triazol-1-yl 1015 Me CH2CO(4-Me Ph) 2-SOMe 1,2,3-triazol-1-yl 1016 Me CH2CO(4-Me Ph) 2-Br 1,2,4-triazol-1-yl 1017 H CH2CO(4-Me Ph) 2-CF3 1,2,4-triazol-l-yl 1018 Me CH2CO(4-Me Ph) 2-CH2SMe 1,2,4-triazol-1-yl 1019 Me CH2CO(4-Me Ph) 2-Cl 1,2,4-triazol-1-yl 1020 Me CH2CO(4-Me Ph) 2-F 1,2,4-triazol-1-yl 1021 Me CH2CO(4-Me Ph) 2-SMe 1,2,4-triazol-1-yl 1022 Me CH2CO(4-Me Ph) 2-SMe-4-Br 1 ,2,4-triazol- 1 -yl Cpd Rb Q (R2)n (XR3)z No. 1023 Me CH2CO(4-Me Ph) 2-SMe-4-CF3 1,2,4-triazol-1-yl 1024 Me CH2CO(4-Me Ph) 2-SMe-4-Cl 1,2,4-triazol-1-yl 1025 Me CH2CO(4-Me Ph) 2-SMe-4-F 1 ,2,4-triazol- 1 -yl 1026 Me CH2CO(4-Me Ph) 2-SMe-4-SMe 1,2,4-triazol-1-yl 1027 Me CH2CO(4-Me Ph) 2-SO2Me 1,2,4-triazol-1-yl 1028 Me CH2CO(4-Me Ph) 2-SO2Me-4-SO2Me 1,2,4-triazol-1-yl 1029 Me CH2CO(4-Me Ph) 2-SOMe 1,2,4-triazol-1-yl 1030 Me CH2CO(4-Me Ph) 2-Br imidazol-l-yl 1031 Me CH2CO(4-Me Ph) 2-CF3 imidazol-1-yl 1032 Me CH2CO(4-Me Ph) 2-CH2SMe imidazol-l-yl 1033 Me CH2CO(4-Me Ph) 2-Cl imidazol-1-yl 1034 Me CH2CO(4-Me Ph) 2-F imidazol-1-yl 1035 Me CH2CO(4-Me Ph) 2-SMe. imidazol-1-yl 1036 Me CH2CO(4-Me Ph) 2-SMe-4-Br imidazol-l-yl 1037 Me CH2CO(4-Me Ph) 2-SMe-4-CF3 imidazol-1-yl 1038 Me CH2CO(4-Me Ph) 2-SMe-4-Cl imidazol-1-yl 1039 Me CH2CO(4-Me Ph) 2-SMe-4-F imidazol-1-yl 1040 Me CH2CO(4-Me Ph) 2-SMe-4-SMe imidazol-1-yl 1041 Me CH2CO(4-Me Ph) 2-SO2Me imidazol-1-yl 1042 Me CH2CO(4-Me Ph) 2-SO2Me-4-SO2Me imidazol-1-yl 1043 Me CH2CO(4-Me Ph) 2-SOMe imidazol- 1 -yl 1044 Me CH2CO(4-Me Ph) 2-Br ~ tetrazol- 1 -yl 1045 Me CH2CO(4-Me Ph) 2-CF3 tetrazol-1-yl 1046 Me CH2CO(4-Me Ph) 2-CH2SMe tetrazol-l-yl 1047 Me CH2CO(4-Me Ph) 2-Cl tetrazol-1-yl 1048 Me CH2CO(4-Me Ph) 2-F tetrazol- 1 -yl 1049 Me CH2CO(4-Me Pb) 2-SMe tetrazol- 1 -yl 1050 Me CH2CO(4-Me Ph) 2-SMe-4-Br tetrazol-1-yl 1051 Me CH2CO(4-Me Ph) 2-SMe-4-CF3 tetrazol- 1 -yl 1052 Me CH2CO(4-Me Ph) 2-SMe-4-Cl tetrazol-1-yl 1053 Me CH2CO(4-Me Ph) 2-SMe-4-F tetrazol-1-yl 1054 Me CH2CO(4-Me Ph) 2-SMe-4-SMe tetrazol-1-yl 1055 Me CH2CO(4-Me Ph) 2-SO2Me tetrazol-1-yl 1056 Me CH2CO(4-Me Ph) 2-SO2Me-4-SO2Me tetrazol-1-yl 1057 Me CH2CO(4-Me Pb) 2-SOMe tetrazol-1-y1 1058 Me CH2(4-Me Ph) 2-Br 1,2,3-triazol-1-yl 1059 Me CH2(4-Me Ph) 2-CF3 1,2,3-triazol-1-yl 1060 Me CH2(4-Me Ph) 2-CH2SMe 1,2,3-triazol-1-yl 1061 Me CH2(4-Me Ph) 2-Cl 1,2,3-triazol-1-yl 1062 Me CH2(4-Me Ph) 2-F 1,2,3-triazol-1-yl 1063 Me CH2(4-Me Ph) 2-SMe 1,2,3-triazol-1-yl Cpd Rb Q (R2)n (XR3)z No. 1064 Me CH2(4-Me Ph) 2-SMe-4-Br 1,2,3-triazol-1-yl 1065 Me CH2(4-Me Ph) 2-SMe-4-CF3 1,2,3-triazol-1-yl 1066 Me CH2(4-Me Ph) 2-SMe-4-Cl 1,2,3-triazol-l-yl 1067 Me CH2(4-Me Ph) 2-SMe-4-F 1,2,3-triazol-1-yl 1068 Me CH2(4-Me Ph) 2-SMe-4-SMe 1,2,3-triazol-1-yl 1069 Me CH2(4-Me Ph) 2-SO2Me 1,2,3-triazol-1-yl 1070 Me CH2(4-Me Ph) 2-SO2Me-4-SO2Me 1,2,3-triazol-1-yl 1071 Me CH2(4-Me Ph) 2-SOMe 1,2,3-triazol-1-yl 1072 Me CH2(4-Me Ph) 2-Br 1,2,4-triazol-1-yl 1073 H CH2(4-Me Ph) 2-CF3 1,2,4-triazol-1-yl 1074 Me CH2(4-Me Ph) 2-CH2SMe 1,2,4-triazol-1-yl 1075 Me CH2(4-Me Ph) 2-Cl 1,2,4-triazol-1-yl 1076 Me CH2(4-Me Ph) 2-F 1,2,4-triazol-1-yl 1077 Me CH2(4-Me Ph) 2-SMe 1,2,4-triazol-1-yl 1078 Me CH2(4-Me Ph) 2-SMe-4-Br 1 ,2,4-triazol- 1 -yl 1079 Me CH2(4-Me Ph) 2-SMe-4-CF3 l,2,4-triazol-1-yl 1080 Me CH2(4-Me Ph) 2-SMe-4-Cl 1,2,4-triazol-1-yl 1081 Me CH2(4-Me Ph) 2-SMe-4-F 1 ,2,4-triazol- 1 -yI 1082 Me CH2(4-Me Ph) 2-SMe-4-SMe 1,2,4-triazol-1-yl 1083 Me CH2(4-Me Ph) 2-SO2Me 1,2,4-triazol-1-yl 1084 Me CH2(4-Me Ph) 2-SO2Me-4-SO2Me 1,2,4-triazol-1-yl 1085 Me CH2(4-Me Ph) 2-SOMe 1,2,4-triazol-1-yl 1086 Me CH2(4-Me Ph) 2-Br imidazol-1-yl 1087 Me CH2(4-Me Ph) 2-CF3 imidazol-1-yl 1088 Me CH2(4-Me Ph) 2-CH2SMe imidazol-1-yl 1089 Me CH2(4-Me Ph) 2-Cl imidazol-1-yl 1090 Me CH2(4-Me Ph) 2-F imidazol- 1 -yl 1091 Me CH2(4-Me Ph) 2-SMe imidazol- 1 -yl 1092 Me CH2(4-Me Ph) 2-SMe-4-Br imidazol-1-yl 1093 Me CH2(4-Me Ph) 2-SMe-4-CF3 imidazol-1-yl 1094 Me CH2(4-Me Ph) 2-SMe-4-Cl imidazol-1-yl 1095 Me CH2(4-Me Ph) 2-SMe-4-F imidazol-1-yl 1096 Me CH2(4-Me Ph) 2-SMe-4-SMe imidazol- 1 -yl 1097 Me CH2(4-Me Ph) 2-SO2Me imidazol-1-yl 1098 Me CH2(4-Me Ph) 2-SO2Me-4-SO2Me imidazol-1-yl 1099 Me CH2(4-Me Ph) 2-SOMe imidazol-1-yl 1100 Me CH2(4-Me Ph) 2-Br tetrazol-1-yl 1101 Me CH2(4-Me Ph) 2-CF3 tetrazol-1-yl 1102 Me CH2(4-Me Ph) 2-CH2SMe tetrazol-1-yl 1103 Me CH2(4-Me Ph) 2-Cl tetrazol-1-yl 1104 Me CH2(4-Me Ph) 2-F tetrazol-1-yl

Cpd Rb Q (R2)n (XR3)z No. 1105 Me CH2(4-Me Ph) 2-SMe tetrazol-l-yl 1106 Me CH2(4-Me Ph) 2-SMe4-Br tetrazol-1-yl 1107 Me CH2(4-Me Ph) 2-SMe-4-CF3 tetrazol-1-yl 1108 Me CH2(4-Me Ph) 2-SMe-4-Cl tetrazol-1-yl 1109 Me CH2(4-Me Ph) 2-SMe-4-F tetrazol-1-yl 1110 Me CH2(4-Me Ph) 2-SMe-4-SMe tetrazol- 1 -yl 1111 Me CH2(4-Me Ph) 2-SO2Me tetrazol-1-yl 1112 Me CH2(4-Me Ph) 2-SO2Me-4-SO2Me tetrazol-l-yl 1113 Me CH2(4-Me Ph) 2-SOMe tetrazol-l-yl The following compounds of formula (Id) also form part of the present invention.

TABLE 9 Cpd No. Ra Rb Q (R2)n (XR3)z 1188 Et H H 2-CF3 4-( 1 ,2,4-triazol- 1 -yl) 1189 Et H SO2(4-Me Ph) 2-CF3 4-(1,2,4-triazol-1-yl) 1190 Et H CH2CO(4Me Ph) 2-CF3 4-(1,2,4-triazol-1-yl) 1191 Et H CH2(4Me Ph) 2-CF3 4-(1,2,4-triazol-1-yl) 1192 Et Me H 2-CF3 4-( 1 ,2,4-triazol- 1 -yl) 1193 Et Me SO2(4-Me Ph) 2-CF3 4-(1,2,4-triazol-1-yl) 1194 Et Me CH2CO(4Me Ph) 2-CF3 4-(1,2,4-triazol-1-y1) 1195 Et Me CH2(4Me Ph) 2-CF3 4-(1,2,4-triazol-1-yl) 1196 Et H H 4-CF3 2-(1,2,4-triazol-1-yl) 1197 Et H SO2(4-Me Ph) 4-CF3 2-(1,2,4-triazol-1-yl) 1198 Et H CH2CO(4Me Ph) 4-CF3 2-(1,2,4-triazol-1-yl) 1199 Et H CH2(4Me Ph) 4-CF3 2-(1,2,4-triazol-1-yl) 1200 Et Me H 4-CF3 2-(1,2,4-triazol-1-yl) 1201 Et Me SO2(4-Me Ph) 4-CF3 2-(1,2,4-triazol-1-yl) 1202 Et Me CH2CO(4Me Ph) 4-CF3 2-(1,2,4-triazol-1-yl) 1203 Et Me CH2(4Me Ph) 4-CF3 2-(1,2,4-triazol-1-yl) Compounds of formula (I) may be prepared by the application or adaptation of known methods (i.e. methods heretofore used or described in the literature), for example as hereinafter described.

In the following description where symbols appearing in formulae are not specifically defined, it is to be understood that they are "as hereinbefore defined" in accordance with the first definition of each symbol in the specification.

It is to be understood that in the descriptions of the following processes the sequences may be performed in different orders, and that suitable protecting groups may be required to achieve the compounds sought.

It is understood that when a process of the invention leads to the formation of a mixture of (Ia) and (Ib), these compounds may be separated by known methods.

According to a feature of the present invention compounds of formula (Ia) or (Ib) in which R represents hydrogen and R1, R2, R3, X, z and n are as defined above may be prepared by the reaction of a compound of formula (III): wherein L is a leaving group and Rl, R2, R3, X, z and n are as hereinbefore defined, with hydroxylamine or a salt of hydroxylamine.

Hydroxylamine hydrochloride is generally preferred. Generally L is alkoxy, for example ethoxy, or N,N-dialkylamino, for example dimethylamino. The reaction is generally carried out in an organic solvent such as ethanol or acetonitrile or a mixture of a water-miscible organic solvent and water, preferably in a ratio of organic solvent: water of from 1:99 to 99: 1, optionally in the presence of a base or acid acceptor such as triethylamine or sodium acetate at a temperature from room temperature to the boiling point of the solvent. Compounds of formula (III) wherein X represents -(CR9R1 0)v and v represents zero are novel and as such constitute a further feature of the present invention.

According to a further feature of the present invention compounds of formula (Ia) in which R represents hydrogen and R1, R2, R3, X, z and n are as defined above may be prepared by the reaction of a compound of formula (IV):

wherein R1 is as hereinbefore defined and Y' represents a carboxy group or a reactive derivative thereof (such as a carboxylic acid chloride or carboxylic ester), or a cyano group, with an appropriate organometallic reagent such as a Grignard reagent or an organolithium reagent. The reaction is generally carried out in an inert solvent such as ether or tetrahydrofuran at a temperature from OOC to the reflux temperature of the mixture.

According to a further feature of the present invention compounds of formula (Ia) or (Ib) wherein R represents -C02R4 and R1, R2, R3, X, z and n are as defined above, may be prepared by the reaction of a salt of a compound of formula (V): wherein R1, R2, R3, X, z and n are as hereinbefore defined with a compound of formula R402CC(Z1)=NOH wherein R4 is as hereinbefore defined and Z1 represents halogen preferably chlorine.

Preferred salts include sodium or magnesium salts. The reaction is generally performed in an inert solvent such as dichloromethane or acetonitrile at a temperature between room temperature and the reflux temperature of the mixture. The salt of a compound of formula (V) is generally prepared in-situ by treating the compound of formula (V) with a base. Examples of suitable bases include alkaline earth metal alkoxides such as magnesium methoxide. Compounds of formula (V) wherein X represents -(CR9R1 0)v- and v represents zero are novel and therefore constitute a further feature of the present invention.

According to a further feature of the present invention compounds of general formula (Ib) in which R represents hydrogen and R1, R2, R3,

X, z and n are as defined above may be prepared by the reaction of a compound of formula (VI): in which D1 represents a carboxy group, or a reactive derivative thereof (such as a carboxylic acid chloride or carboxylic ester), or a cyano group, with an appropriate organometallic reagent (for example Grignard or organolithium reagent), preferably of formula RlMl in which M1 is a metal halide such as magnesium bromide or a metal such as lithium. The reaction is generally carried out in an inert solvent such as ether or tetrahydrofuran, at a temperature from OOC to the reflux temperature of the solvent. Compounds of formula (VI) wherein X represents -(CR9R10)v- and v represents zero are novel and therefore constitute a further feature of the invention.

According to a further feature of the present invention compounds of formula (Ia) and (Ib) wherein R, R1, R2, R3, X, z and n are as defined above, may be prepared by the reaction of a compound of formula (VII) or (VIII) respectively: wherein R, Rl, R;, Rb, z and n are as defined above and Y2 represents a leaving group for example halogen (preferably fluoro), with a compound of formula R3-H. The reaction is generally performed in the presence of a base, for example sodium hydride or caesium carbonate, in an inert solvent, for example N,N-dimethylformamide at a

temperature from OOC to 100°C. The reaction is preferably carried out using compounds in which Rrepresents -C02R4.

According to a further feature of the present invention compounds of formula (Ic) may be prepared from the corresponding compound of formula (Ia) or (Ib) in which R is as defined above. Where R represents a hydrogen atom the reaction is preferably carried out by treatment with a base. Examples of suitable bases include alkali or alkaline earth metal hydroxides, alkoxides such as sodium ethoxide or organic bases such as triethylamine. Where R represents -C02R4 the conversion is generally carried out by a hydrolytic reaction. The hydrolytic reaction may be performed in the presence of an acid or base. Acidic hydrolysis may be achieved for example using aqueous hydrochloric acid. Basic hydrolysis may be achieved for example using sodium hydroxide in a mixture of alcohol and water. The reactions are preferably carried out at a temperature between 200C and the reflux temperature of the mixture.

According to a further feature of the present invention, compounds of formula (Ic) in which R1, R2, R3, X, z and n are as defined above may also be prepared by the reaction of a benzoyl chloride of formula (IX): wherein R2, R3, X, z and n are as hereinbefore defined, with a beta-ketonitrile of formula (X): R1 C(=O)CH2CN (x) wherein R1 is as hereinbefore defined. The reaction is generally performed in the presence of a base, in a solvent or solvent mixture.

Suitable bases include metal hydrides, hydroxides or alkoxides (e.g. sodium or lithium hydride, sodium hydroxide, potassium hydroxide, magnesium ethoxide or magnesium methoxide). Suitable solvents include for example tetrahydrofuran; hydrocarbons such as toluene; or halogenated hydrocarbons such as dichloromethane. The reaction is

generally performed at a temperature from OOC to the reflux temperature.

According to a further feature of the present invention, compounds of formula (Ic) in which R1, R2, R3, X, z and n are as defined above may also be prepared by the reaction of an acid chloride of formula K1 COCI wherein R1 is as hereinbefore defined, with a beta-ketonitrile of formula (XI): wherein R2, R3, X, z and n are as hereinbefore defined. The reaction is generally performed under the same conditions as described above for the reaction of compounds of formula (IX) with compounds of formula (X).

According to a further feature of the present invention compounds of formula (Ic) in which R1, R2, R3, X, z and n are as defined above may also be prepared by the reaction of a benzoyl chloride of formula (IX) above wherein R2, R3, X, z and n are as hereinbefore defined, with a beta-ketonitrile of formula (X) wherein R1 is as hereinbefore defined, via an intermediate of formula (XII): wherein R1, R2, R3, X, z and n are as hereinbefore defined. The formation of the intermediate of formula (XII) may be carried out in the presence of a mild base such as an organic base e.g. triethylamine, in an inert solvent such as acetonitrile or dichloromethane at a temperature between room temperature and the reflux temperature of the mixture.

The rearrangement of the intermediate of formula (XII) to a compound of formula (Ic) is generally carried out in situ in an inert solvent such as

acetonitrile or dichloromethane in the presence of a catalyst such as a source of cyanide. Examples of such sources of cyanide are acetone cyanohydrin or an alkali metal cyanide such as potassium cyanide, optionally in the presence of a crown ether such as 1 8-crown-6.

According to a further feature of the present invention compounds of formula (Ic) in which R1, R2, R3, X, z and n are as defined above, may be prepared by the reaction of an acid chloride of formula RlCOCl wherein R1 is as hereinbefore defined, with a beta-ketonitrile of formula (XI) wherein R2, R3, X, z and n are as hereinbefore defined via an intermediate of formula (XIII): wherein R1, R2, R3, X, z and n are as hereinbefore defined. The formation and rearrangement of the intermediate of formula (XIII) is generally carried out under the same conditions as described above for the formation and rearrangement of compounds of formula (XII).

According to a feature of the present invention compounds of formula (Id) wherein Ra, Rb, R2, R3, X, n and z are as defined above and Q represents hydrogen may be prepared by the reaction of a compound of formula (XIV): wherein Ra and Rb are as defined above, with a carboxylic acid of formula (XV):

wherein R2, R3, X, n and z are as defined above. The compounds of formula (XIV) may exist as the tautomer (XIVa) and both forms may be used. The reaction is generally performed in the presence of a coupling agent, generally a carbodiimide such as N,N1- dicyclohexylcarbodiimide. One to 1.5 equivalents of the coupling agent are generally used. The reaction is preferably conducted in the presence of a base such as an alkali metal carbonate preferably potassium carbonate, and in a solvent such as an alcohol for example t-amyl alcohol, t-butanol or i-propanol, and at a temperature of about 200C to the reflux temperature of the solvent and preferably 50-1 000C.

According to a further feature of the present invention compounds of formula (Id) wherein Ra, Rb, R2, R3, X, n and z are as defined above and Q represents hydrogen may also be prepared by the reaction of a compound of formula (XIV) or (XIVa) above with an acid chloride of formula (IX) wherein R2, R3, X, n and z are as defined above, to give an ester of formula (XVI): followed by rearrangement to give the compound of formula (Id).

The first stage of this process to give the ester intermediates of formula (XVI) is generally performed in the presence of a base such as potassium carbonate, triethylamine or pyridine, and in a solvent such as toluene, acetone, dichloromethane, acetonitrile or tetrahydrofuran, at a temperature of from 0-600C. The rearrangement process to give the compounds of formula (Id) wherein Q is hydrogen is generally performed using a Lewis acid such as aluminium chloride; or preferably

using a base for example potassium carbonate or calcium hydroxide.

One to ten equivalents of the base are used, optionally in the presence of a solvent such as acetone, methyl ethyl ketone, t-amyl alcohol, t- butanol, dioxan, toluene or xylene, at a temperature of 50-1 500C. The rearrangement process is preferably performed in the presence of a catalytic amount of the corresponding compound of formula (XIV).

Alternatively the rearrangement process may be performed in the presence of a source of cyanide in the presence of a base. Cyanide sources include metal cyanides for example alkali metal cyanides such as sodium cyanide, hydrogen cyanide, or cyanhydrins of dialkyl ketones preferably acetone cyanhydrin. Generally up to 0.5 equivalent (preferably 0.1 equivalent) of cyanide source is employed. Suitable bases include trialkylamines such as triethylamine, or pyridine or alkali metal carbonates such as potassium carbonate. Generally 1-4 equivalents (preferably 2 equivalents) of the base is used. Solvents which may be used include toluene, acetonitrile, dichloromethane or preferably 1,2-dichloroethane. The reaction is generally performed at a temperature of from 00C-600C (generally at 200C-300C).

Compounds of formula (XVI) are novel and as such constitute a further feature of the invention.

According to a further feature of the present invention compounds of formula (Id) wherein Ra, Rb, R2, R3, X, n and z are as defined above and Q represents hydrogen may also be prepared by the reaction of a compound of formula (XIV) above with an aryl halide of formula (XVII): wherein R2, R3, X, n and z are as defined above and T represents a bromine or iodine atom, in the presence of carbon monoxide and a palladium, nickel, cobalt or rhodium catalyst preferably bis(triphenylphosphine)palladium (II) chloride. The reaction is conducted in the presence of a base generally a trialkylamine such as

triethylamine in a solvent which may be water and a phase transfer catalyst for example tetrabutylammonium bromide.

According to a further feature of the present invention compounds of formula (Id) wherein Ra, Rb, R2, R3, X, n and z are as defined above and Q represents According to a further feature of the present invention compounds of formula (Id) wherein Ra, Rb, R2, R3, X, n and z are as defined above and Q represents -S02R4, -S02R20, -COR12, -COR20, -COCH20C(O)R16, -COCH2OR12, -COCH2OR20, -CONR5R6, -CONR20R21, -CoNR22R23, -C02R12, -CO2R20 or -P(O)RSaRSb, may be prepared by the reaction of the corresponding compound of formula (Id) wherein Q represents hydrogen, with an appropriately substituted sulphonyl halide, acyl halide, phosphonyl halide or phosphinyl halide (chlorides are the preferred halides). The reaction is generally performed using the same conditions as are employed for the above preparation of compounds of formula (Id) wherein Q represents alkyl and related derivatives.

According to a further feature of the present invention compounds in which p or q is one or two may be prepared by the oxidation of the sulphur atom of the corresponding compounds in which p or q is 0 or 1.

The oxidation of the sulphur atom is generally carried out using for example 3-chloroperoxybenzoic acid in an inert solvent such as dichloromethane at a temperature from -400C to room temperature.

Intermediates in the preparation of compounds of formula (Ia), (Ib), (Ic) and (Id) may be prepared by the application or adaptation of known methods.

Compounds of formula (III) may be prepared by the reaction of compounds of formula (V) with either a trialkyl orthoformate such as triethyl orthoformate or a dimethylformamide dialkyl acetal such as dimethylformamide dimethyl acetal.

The reaction with a trialkyl orthoformate can be carried out in the presence of acetic anhydride at the reflux temperature of the mixture and the reaction with dialkylformamide dialkyl acetal can be carried out optionally in the presence of an inert solvent at a temperature from room temperature to the reflux temperature of the mixture.

Compounds of formula (V) may be prepared by the reaction of an acid chloride of formula (IX) with a metal salt of a compound of formula (XVIII): wherein R1 is as hereinbefore defined, to give a compound of formula (XIX): wherein R1, R2, R3, X, z and n are as hereinbefore defined, which is subsequently decarboxylated to give a compound of formula (V).

Generally the reaction to produce the compound of formula (XIX) is performed in a solvent such as a lower alcohol, preferably methanol, in the presence of a metal, preferably magnesium. The reaction may also be performed using a pre-prepared metal salt of a compound of formula (XVIII). The decarboxylation is generally performed by refluxing the compound of formula (XIX) in the presence of a catalyst, such as para-toluenesulphonic acid or trifluoroacetic acid, in an inert solvent e.g. toluene or 1,2-dichloroethane.

Compounds of formula (V) may also be prepared by the reaction of a benzoic acid ester of formula (XX): wherein R2, R3, X, z and n are as hereinbefore defined and R24 represents a lower alkyl group (preferably methyl), with a compound of formula (XXI):

R1-C(O)-CH3 (XXI) wherein R1 is as hereinbefore defined. The reaction is generally performed in a solvent such as ether, tetrahydrofuran or N,N- dimethylformamide, in the presence of a base, preferably an alkali metal base such as sodium hydride, at a temperature from OOC to the reflux temperature. A number of compounds of formula (XX) wherein X represents -(CR9R10)v- and v represents zero are novel and as such constitute a further feature of the present invention.

Intermediates of formula (VII) or (VIII) may be prepared by any of the processes described above for the preparation of a compound of formula (Ia) or (Ib) from the corresponding compounds of formula (III), (IV), (V) or (VI).

Acid chlorides of formula (IX) may be prepared by the reaction of a benzoic acid of formula (XV) with a chlorinating agent, for example thionyl chloride at the reflux temperature of the mixture. In some cases the benzoyl chlorides may also be prepared by reaction of the benzoic acid with oxalyl chloride in a solvent such as 1,2-dichloroethane at from ambient to reflux temperature.

A number of the benzoic acids of formula (XV) wherein X represents -(CR9R10)v- and v represents zero are novel and as such constitute a further feature of the present invention.

Esters of formula (XX) may be prepared from acids of formula (XV) according to known methods.

Compounds of general formula (VI) wherein D1 is -C02-alkyl or -CN may be prepared by the reaction of compounds of general formula (XXII): wherein G1 represents C02-alkyl or -CN and L is as hereinbefore defined, with a salt of hydroxylamine such as hydroxylamine hydrochloride, in a solvent such as ethanol or acetonitrile, optionally in

the presence of a base or acid acceptor such as triethylamine or sodium acetate.

Compounds of general formula (VI) in which D1 represents a carboxylic acid or carboxylic acid chloride may be prepared from the corresponding compound of general formula (VI) in which D1 represents a carboxylic ester group by the hydrolysis of said ester group and conversion, as necessary, of the acid thus obtained to the acid chloride, e.g. by heating with thionyl chloride.

Compounds of general formula (XXII) may be prepared by the reaction of a ketonitrile of formula (XI) or a ketoester of formula (XXIII): with either triethyl orthoformate in the presence of acetic anhydride at the reflux temperature of the mixture or with dimethylformamide dimethylacetal optionally in an inert solvent such as toluene at a temperature from room temperature to the reflux temperature of the mixture.

Beta-ketonitriles of formula (X) may be prepared from acid chlorides of formula R1 COCl by a number of methods well known in the chemical literature. For example, see Krauss, et al, Synthesis, 1983, 308, or Muth, et al, J. Org. Chem, 1960, 25, 736. Alternatively beta- ketonitriles of formula (X) may be prepared by the reaction of an ester of formula Rl-CO2Et, wherein R1 is as hereinbefore defined, with acetonitrile. This reaction is described in the literature, for example see the article by Abramovitch and Hauser, J.Am. Chem. Soc., 1942, 64 2720.

Beta-ketonitriles of formula (XI) may be prepared from benzoyl chlorides of formula (IX) or from corresponding ethyl benzoates in a manner analogous to the preparation of beta-ketonitriles of formula (X) set forth above.

Benzoic acids of formula (XV) or esters of formula (XX) in which R2, R3, R24, X, z and n are as defined above, may be prepared by the reaction of the corresponding compound of formula (XV) or (XX) in which R3 is replaced by a Y2 (Y2 is as defined above preferably fluorine), with a compound of formula R3-H using the same procedure as described above for the preparation of compounds of formula (Ia) and (Ib) from compounds of formula (VII) and (VIII).

Intermediates of formula (IV), (XIV), (XVIII), (XXI) and (XXIII), are known or may be prepared by the application or adaptation of known methods.

Those skilled in the art will appreciate that some compounds of formula (I) may be prepared by the interconversion of other compounds of formula (I) and such interconversions constitute yet more features of the present invention.

The following non-limiting Examples illustrate the preparation of compounds of formula (I) and the Reference Examples illustrate the preparation of intermediates in their synthesis. NMR Spectra are recorded as d (ppm) in deuterochloroform as solvent (unless ortherwise stated).

Example 1 Ethyl 5-cyclopropyl4-(4-fluoro-2- trifluoromethyl)benzoylisoxazole-3-carboxylate (0.74g) was added to a suspension of sodium hydride (60%, 0.12g) and 1,2,4-triazole (0.21g) in dry N,N-dimethylformamide at 200C. The solution was stirred for 3 hours, poured into water, extracted (ethyl acetate), dried (magnesium sulphate) and evaporated. The residue was purified by chromatography to give ethyl 5-cyclopropyl-4-[4-(1,2,4-triazol-1-yl)-2- trifluoromethylbenzoyl] isoxazole-3-carboxylate as a colourless solid (Compound 1, 0.79g), NMR 1.25(m,2H), 1.40(m,2H), 1.19(t,3H), 2.46(m, 1 H), 4.09(q,2H), 7.65(d, 1 H), 8.00(dd, 1 H), 8.1 6-8.23(m,3H), 8.80(s, 1 H).

By proceeding in a similar manner the following compounds were also prepared: ethyl 5-cyclopropyl-4-[4-(3-methylthio- 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]isoxazole-3-carboxylate (Compound 2), NMR

1.25(m,2H), 1.38(m,2H), 1.1 9(t,3H), 2.47(m,1H), 2.70(s,3H), 4.09(q,2H), 7.61(d,1H), 7.92(dd,1H), 8.12(d,1H), 8.66(s,1H); ethyl 5-cyclopropyl-4-[4-( 1 ,2,4-triazol- 1 -yl)naphth- 1 - oyl]isoxazole-3-carboxylate (Compound 3), NMR 1.18(m,2H), 1.37(m,2H), 1.92(t,3H), 2.39(m,1H), 3.92(q,2H), 7.50-7.85(m,5H), 8.28(s,1H), 8.48(s,1H), 8.58(d,1H); ethyl 5-cyclopropyl-4- [2-chloro-4-(1,2,4-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 4), NMR 1.20- 1.40(m,4H), 1.23(t,3H), 2.45(m,1H), 4.15(q,2H), 7.62-7.90(m,3H), 8.15(s,lH), 8.69(s,1H); ethyl 5-cyclopropyl4-[2-iodo4-( 1 ,2,4-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 5), NMR 1.20- 1.40(m,4H), 1.24(t,3H), 2.40(m, 1 H), 4.15(q,2H), 7.52(d,1H),7.78(m,1H), 8.15(s,1H), 8.37(m,1H), 8.66(s,1H); ethyl 5-cyclopropyl-4-[2-methyl-4-( 1 ,2,4-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 6), NMR 1.15- 1.40(m,4H), 1.1 9(t,3H), 2.32(m,1H), 2.64(s,3H), 4.11(q,2H), 7.55(m,2H), 7.70(s,1H), 8. 14(s,1H), 8.65(s,1H); ethyl 5-cyclopropyl4- [2-benzyl-4-( 1 ,2,4-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 7), NMR 1.15- 1.30(m,4H), 1.22(t,3H), 2.00(m,1H), 4.1 8(q,2H), 4.34(s,2H),7.20- 7.65(m,8H), 8.11(s,1H), 8.55(s,1H); ethyl 5-cyclopropyl4-[4-(imidazol-1 -yl)-2- trifluoromethylbenzoyl]isoxazole-3-carboxylate (Compound 8), NMR 1.25(m,2H), 1.38(m,2H), 1.1 9(t,3H), 2.50(m,1H), 4.09(q,2H), 7.28(d,1H), 7.39(d,1H), 7.64(m,2H), 7.82(d,1H), 7.98(s,1H); ethyl 5-cyclopropyl-4- [4-(imidazol- 1 -yl)naphth- 1 -oyl] isoxazole-3 - carboxylate (Compound 9), NMR 1.25(m,2H), 1.38(m,2H), 0.90(t,3H), 2.42(m,1 H), 3.90(q,2H), 7.25-7.80(m,7H), 8.60(d, 1 H); ethyl 5-cyclopropyl-4-[2-chloro-4-(imidazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 10), NMR 1.20- 1.45(m,4H), 1.23(t,3H), 2.46(m,1H), 4.16(q,2H), 7.23-7.53(m,4H), 7.65(d,1H),7.95(s,lH); ethyl 5-cyclopropyl-4-[4-(imidazol- 1-yl)-2- iodobenzoyl]isoxazole-3-carboxylate (Compound 11), NMR 1.18-

1.42(m,4H), 1.23(t,3H), 2.40(m, 1 H), 4.14(q,2H), 7.25(s,1H),7.33(m,1H), 7.50(m,2H),7.93(s,1H), 8.02(m,1H); ethyl 5-cyclopropyl-4-[4-(pyrazol-1-yl)-2- trifluoromethylbenzoyl]isoxazole-3-carboxylate (Compound 12), NMR 1.20-1.40(m,4H), 1.21(t,3H), 2.40(m, 1 H), 4.10(q,2H), 6.57(m,1H), 7.59(d,1H), 7.80(d, 1 H), 7.92(dd,1H), 8.04(d, 1 H), 8.20(d,1H); ethyl 5-cyclopropyl1-4[2-chloro-4-(pyrazol-1- yl)benzoyl]isoxazole-3-carboxylate (Compound 13), NMR 1.18- 1 .40(m,4H), 1 .23(t,3H), 2.38(m, 1H), 4.1 8(q,2H), 6.54(m,lH), 7.58- 8.04(m,5H).

By proceeding in a similar manner and heating at 500C the following compounds were also prepared: ethyl 5-cyclopropyl-4-[2,3-bis-(methylthio)-4-(1,2,4-triazol-1- yl)benzoyl]isoxazole-3-carboxylate (Compound 21), NMR 1.2 (t,3H), 1.1 - 1.4 (m,4H) , 2.1 (s,3H), 2.4 (bs,4H) , 4.1 (q,2H) , 7.3 (d,1H) , 7.4 (d,lH), 8.1 (s,lH) ,8.6 (s,lH); ethyl 5-cyclopropyl-4-[2,3-bis-(methylthio)-4-(imidazol-1- yl)benzoyl]isoxazole-3-carboxylate (Compound 22), NMR 1.2 (t,3H), 1.2 - 1.4 (m,4H), 2.0 (s,3H) ,2.4 (s,3H) ,2.5 (m,lH) ,4.1 (q,2H) ,7.2 - 7.4 (m,4H), 7.8 (s,lH); ethyl 5-cyclopropyl-4-[3-fluoro-2-methylthio-4-(1,2,4-triazol-1- yl)benzoyl]isoxazole-3-carboxylate (Compound 23), NMR 1.2 (t,3H), <BR> <BR> <BR> 1.2 - 1.4 (m,4H) ,2.3 (m,lH) ,2.4 (s,3H) 4.1 (q,2H) , 7.3 (d,1H), 7.8<BR> <BR> <BR> <BR> <BR> <BR> <BR> (m,1H) , 8.1 (s,1H) , 8.7 (s,lH); ethyl 5-cyclopropyl-4-[2-methylthio-3,4-bis-(1,2,4-triazol-1- yl)benzoyl]isoxazole-3-carboxylate (Compound 24), NMR 1.2 (t,3H), 1.1 - 1.4 (m,4H) , 2.0 (s,3H) ,2.5 (m,1H), 4.1 (q,2H), 7.6 (d,1H) , 7.7 (d,lH), 7.9 (s,lH), 8.0 (s,lH)8.2 (s,lH); ethyl 5-cyclopropyl-4-[3-bromo-2-methylthio-4- 1 ,2,4-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 25), NMR 1.2 (t,3H), 1.2 - 1.4 (m,4H) , 2.4 (s,3H) , 2.5 (m,lH), 4.2 (q,2H) , 7.4 (d,1H), 7.5 (d,1H), 8.2 (s,1H), 8.5 (s,1H); ethyl 5-cyclopropyl-4-[2-methylthio-4-(1,2,4-triazol-1- yl)benzoyl]isoxazole-3-carboxylate (Compound 26), NMR 1.1 (t,3H), 1.0 - 1.3 (m,4H), 2.2 (m,1H), 2.5 (s,3H), 4.1 (q,2H), 7.3 (d,1H), 7.6 (d,lH), 7.7 (s,lH), 8.1 (s,lH) , 8.6 (s,1H);

ethyl 5-cyclopropyl-4-[2-methylthio-4-(imidazol-1- yl)benzoyl]isoxazole-3-carboxylate (Compound 27), NMR 1.1 (t,3H), 1.0 - 1.3 (m,4H), 2.1 (m,1H), 2.4 (s,3H), 4.1 (q,2H), 7.1 (d,1H), 7.2 (s,1H), 7.3 (d,2H), 7.5 (d,1H), 7.8 (s,1H); ethyl 5-cyclopropyl-4-[2-ethyl-3-methylthio-4-(1,2,4-triazol-1- yl)benzoyl]isoxazole-3-carboxylate (Compound 28), NMR 1.1 (t,3H), 1.2 (t,3H), 1.0 - 1.3 (m,4H) , 2.3 (m,1H) , 2.9 (s,3H) , 3.1 (q,2H) , 4.1 (q,2H), 7.3 (s,2H), 8.1 (s,lH), 8.7 (s,lH); ethyl 5-cyclopropyl-4-[2-isobutyl-4-(1,2,4-triazol-1- yl)benzoyl]isoxazole-3-carboxylate (Compound 29), NMR 0.9 (d,6H), <BR> <BR> <BR> 1.2 (t,3H), 1.1 - 1.3 (m,4H), 2.0 (m,lH), 2.2 (m,lH) ,2.8 (d,2H) ,4.1 (q,2H), 7.5 (m,2H), 7.6 (s,lH), 8.1 (s,1H) , 8.6 (s,lH); ethyl 5-cyclopropyl-4-[2-isobutyl-4-(imidazol-1- yl)benzoyl]isoxazole-3-carboxylate (Compound 30), NMR 0.9 (d,6H), <BR> <BR> <BR> 1.2 (t,3H), 1.1 - 1.4 (m,4H) ,2.0 (m,1H) 2.2 (m,lH), 2.8 (d,2H) 4.1 (q,2H) , 7.2 - 7.4 (m,4H) , 7.5 (d,lH), 8.0 (s,lH); ethyl 5-cyclopropyl-4-[3-methoxy-2-methylthio-4-(1,2,4-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 31), NMR 1.1 (t,3H), <BR> <BR> <BR> 1.1 - 1.3 (m,4H) ,2.3 (m,lH) ,2.4 (s,3H) '3.7 (s,3H) ,4.1 (q,2H) ,7.2 (d,lH), 7.7 (d,lH), 8.1 (s,1H) , 8.9 (s,lH); ethyl 5-cyclopropyl-4-[2,3-bis-(methylthio)-4-(1,2,3-triazol-2- yl)benzoyl]isoxazole-3-carboxylate (Compound 32), NMR 1.2 (t,3H), <BR> <BR> <BR> 1.2 - 1.4 (m,4H) , 2.1 (s,3H), 2.4 (s,3H) ,2.5 (m,1H) ,4.1 (q,2H) , 7.4 (d,1H), 7.5 (d,1H), 7.9 (s,2H); ethyl 5-cyclopropyl-4-[3-bromo-2-methylthio-4-(1,2,3-triazol-2- yl)benzoyl]isoxazole-3-carboxylate (Compound 33), NMR 1.3 (t,3H), 1.2 - 1.4 (m,4H) , 2.4 (m,1H), 2.4 (s,3H), 4.2 (q,2H), 7.4 (d,lH), 7.5 (d,lH), 7.9 (s,2H); ethyl 5-cyclopropyl-4- [3-bromo-2-methylthio-4-( 1,2,3 -triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 34), NMR 1.2 (t,3H), 1.2 - 1.4 (m,4H), 2.4 (s,3H), 2.5 (m,1H) , 4.2 (q,2H), 7.4 (d,1H) , 7.5 (d,lH), 7.9 (s,lH), 8.0 (s,lH); ethyl 5-cyclopropyl-4-[2-methylthio-4-(1,2,3-triazol-2- yl)benzoyl]isoxazole-3-carboxylate (Compound 35), NMR 1.1 - 1.4 (m,4H), 1.1 (t,3H), 2.2 (m,lH), 2.6 (s,3H) , 4.1 (q,2H) , 7.6 (d,lH), 7.9 (m,3H), 8.1 (s,1H);

ethyl 5-cyclopropyl-4-[2,3-bis-(methylthio)-4-(3-methyl-1,2,4- triazol-l-yl)benzoyl]isoxazole-3-carboxylate (Compound 36), NMR 1.2 (t,3H), 1.1 - 1.4 (m,4H), 2.1 (s,3H), 2.3 (m,1H), 2.4 (s,3H), 2.5 (s,3H), 4.1 (q,2H) , 7.4 (d,lH) , 7.5 (d,lH) , 8.5 (s,lH); ethyl 5 -cyclopropyl4- [3 -bromo-2-methylthio-4-(3 -methyl-1,2,4- triazol-1-yl)benzoyl]isoxazole-3-carboxylate (Compound 37), NMR 1.2 (t,3H), 1.2 - 1.4 (m,4H) , 2.3 (m,lH), 2.4 (s,3H), 2.5 (s,3H) , 4.2 (q,2H) , 7.4 (d,lH) , 7.5 (d,lH), 8.4 (s,lH); ethyl 5-cyclopropyl-4-[3 -bromo-2-methylthio-4-(5 -methyl-1,2,4- triazol-4-yl)benzoyl]isoxazole-3-carboxylate (Compound 38), NMR 1.2 - 1.4 (m,4H) , 1.3 (t,3H) , 2.3 (s,3H), 2.4 (s,3H) , 2.5 (m,lH) , 4.1 (q,2H), 7.4 (m,2H), 8.0 (s,lH).

By proceeding in a similar manner and heating at 1 000C the following compounds were also prepared: ethyl 5-cyclopropyl-4-[2-methylthiomethyl-4-(1,2,4-triazol-1- yl)benzoyl]isoxazole-3-carboxylate (Compound 39), NMR 1.2 (t,3H), 1.2 - 1.4 (m,4H) , 2.0 (s,3H) , 2.1 (m,lH) , 4.0 (s,2H) , 4.1 (q,2H) , 7.5 (d,lH), 7.6 (d,lH), 7.8 (s,lH), 8.1 (s,lH), 8.6 (s,lH); ethyl 5-cyclopropyl-4-[2,3-bis-(methylthio)-4-(tetrazol-1- yl)benzoyl]isoxazole-3-carboxylate (Compound 40), NMR 1.2 (t,3H), 1.2 - 1.4 (m,4H) , 2.2 (s,3H) , 2.4 (s,3H) , 2.5 (m,lH) , 4.1 (q,2H) , 7.5 (d,lH), 7.6 (d,lH), 9.1 (s,lH); ethyl 5-cyclopropyl-4-[2-methylthio-4-(tetrazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 41), NMR 1.2 (t,3H), 1.1 - 1.4 (m,4H) , 2.3 (m,lH), 2.6 (s,3H) , 4.2 (q,2H) , 7.4 (d,lH) , 7.7 (d,lH), 7.8 (s,lH), ,9.1 (s,lH); ethyl 5 -cyclopropyl-4- [2-ethyl-3 -methylthio-4-(tetrazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 42), NMR 1.1 (t,3H), 1.2 (t,3H) , 1.1 - 1.4 (m,4H) , 1.9 (s,3H) , 2.4 (m,1H) , 3.1 (q,2H) , 4.0 (q,2H), 7.4 (m,2H), 9.1 (s,lH); ethyl 5-cyclopropyl-4-[2-ethyl-3-methylthio-4-(1,2,3-triazol-2- yl)benzoyl]isoxazole-3-carboxylate (Compound 43), NMK 1.1 - 1.4 <BR> <BR> <BR> (m,4H) , 1.2 (t,3H) , 1.3 (t,3H) ,2.0 (s,3H) 2.3 (m,lH) ,3.2 (q,2H) ,4.1 (q,2H), 7.4 (s,2H), 7.9 (s,2H); ethyl 5 -cyclopropyl-4-[2-ethyl-3 -methylthio4-(1,2,3 -triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 44), NMR 1.1 - 1.4

(m,4H) , 1.2 (t,3H) , 1.3 (t,3H) , 1.9 (s,3H) , 2.4 (m,1H) , 3.1 (q,2H) , 4.1 (q,2H) , 7.4 (s,2H) , 7.9 (s,1H), 8.2 (s,lH); ethyl 5-cyclopropyl-4-[2-isobutyl-4-(1,2,3-triazol-1- yl)benzoyl]isoxazole-3-carboxylate (Compound 45), NMR 0.9 (d,6H), <BR> <BR> <BR> 1.1 (t,3H), 1.0 - 1.3 (m,4H), 1.9 (m,lH) ,2.1 (m,lH) ,2.7 (d,2H) 4.1 (q,2H), 7.5 (d,1H), 7.6 (d,1H), 7.7 (s,1H), 7.8 (s,1H), 8.0 (s,1H); ethyl t-cyclopropyl-4-[2-methylthio-4-(3-methyl- 1 ,2,4-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 46), NMK 1.1 (t,3H), 1.1 - 1.4 (m,4H) , 2.2 (m,lH), 2.5 (s,3H) , 2.6 (s,3H) , 4.1 (q,2H), 7.3 (d,1H), 7.6 (d,1H), 7.7 (s,1H), 8.5 (s,1H); ethyl 5 -cyclopropyl-4- [2-ethyl-3 -methylthio-4-(3 -methyl-1,2,4- triazol-a-yl)benzoyl]isoxazole-3-carboxylate (Compound 47), NMR 1.1 - 1.3 (m,7H), 1.2 (t,3H), 1.9 (s,3H), 2.0 (s,3H) ,2.2 (m,lH) , 3.1 (q,2H), 4.1 (q,2H) , 7.2 (s,lH) , 7.3 (s,2H), 8.5 (s,lH); ethyl 5-cyclopropyl-4- [2-isobutyl-4-(3 -methyl- 1 ,2,4-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 48), NMK 0.9 (d,6H), 1.1 - 1.3 (m,4H), 1.2 (t,3H), 2.0 (m,lH), ,2.1 (m,1H), 2.5 (s,3H), ,2.8 (d,2H), 4.2 (q,2H) , 7.5 (m,2H) , 7.6 (m,lH), 8.5 (s,lH); ethyl 5-cyclopropyl-4-[2-chloro-4-(1,2,3,4-tetrazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 132), NMR 1.2- 1.3(m,5H), 1.3(m,2H), 2.5(m,1H), 4.1(q,2H), 7.7(m,2H), 7.9(d,1H), 9.1(s,1H); ethyl 5-cyclopropyl-4- [2-methyl-4-( 1,2,3 ,4-tetrazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 129), NMR 1.1 - 1.2(m,5H), 1.3(m,2H), 2.3(m,1H), 2.6(s,3H), 4.0(q,2H), 7.5(m,2H), 7.6(s,1H), 9.0(s,1H); ethyl 5-cyclopropyl-4- [8-(1,2,3,4-tetrazol-1 -yl)- 1 ,4-benzoxathian- 5-oyl]isoxazole-3-carboxylate (Compound 429), NMR 1.1-1.3(m,7H), 2.2(m,1H), 3.1(t,2H), 4.1 (q,2H), 4.5(t,2H), 7.3(d, 1 H), 7.5(d, 1 H), 9.1(s,1H); ethyl 5-cyclopropyl-4-[2-chloro-4-(1,2,3-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 160), NMR 1.2(m,5H), 1.3(m,2H), 2.4(m,1H), 4.1(q,2H), 7.7(d,1H), 7.8(d,1H), 7.9(s,1H), 7.9(s,1H), 8.1(s,1H); ethyl 5-cyclopropyl-4- [2-chloro-4-(1,2,3 -triazol-2- yl)benzoyl]isoxazole-3-carboxylate (Compound 173), NMR 1.2(m,5H),

1.3(m,2H), 2.4(m,1H), 4.1(q,2H), 7.6(d,lH), 7.9(s,2H), 8.1(d,1H), 8.2(s,1H); ethyl 5-cyclopropyl-4-[2-trifluoromethyl-4-(1,2,3 -triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 154), NMR l.l(t,3H), 1.2(m,2H), 1.4(m,2H), 2.5(m, 1 H), 4.1(q,2H), 7.6(d, 1 H), 7.9(s,1H), 8.0(d,1H), 8.1(s,1H), 8.2(s,lH); ethyl 5-cyclopropyl-4-[2-trifluoromethyl-4-(1,2,3-triazol-2- yl)benzoyl]isoxazole-3-carboxylate (Compound 167), NMR 1.1 - 1.2(m,5H), 1.3(m,2H), 2.3(m,1H), 4.0(q,2H), 7.5(d,1H), 7.8(s,2H), 8.2(d,1H), 8.5(s,lH); ethyl 5 -cyclopropyl-4- [2-methyl-4-(1,2,3 -triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 158), NMR 1.2(m,5H), 1.3(m,2H), 2.3(m,1H), 2.6(s,3H), 4.1 (q,2H), 7.5(d,1 H), 7.6(d, 1 H), 7.7(s,1H), 7.9(s,1H), 8.0(s,1H); ethyl 5-cyclopropyl-4-[8-(1 ,2,3-triazol-2-yl)- 1,4-benzoxathian-5- oyl]isoxazole-3-carboxylate (Compound 430), NMR 1.1-1.3(m,7H), 2.2(m,lH), 3.1(t,2H), 4.1 (q,2H), 4.4(t,2H), 7.1 (d, 1 H), 7.2(d,1H), 7.8(s,2H); ethyl 5-cyclopropyl-4-[3-methoxy-2-methylthio-4-(1,2,3-triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 431), NMK 1.1 - 1.2(m,5H), 1.3(m,2H), 2.3-2.4(m,4H), 3.6(s,3H), 4.0(q,2H), 7.2(d,lH), 7.7(d,1H), 7.8(s,1H), 8.2(s,lH); ethyl 5-cyclopropyl-4- [2-methylthio4-( 1,2,3 -benztriazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 184), NMR l.l(m,5H), 1.2(m,2H), 2.2(m,1H), 2.5(s,3H), 4.1(q,2H), 7.4(t,1H), 7.5(m,2H), 7.7(m,2H), 7.8(s,1H), 8.1(d,lH); ethyl 5-cyclopropyl-4-[2-methylthio-4-( 1,2,3 -triazol- 1 - yl)benzoyl]isoxazole-3-carboxylate (Compound 155), NMR 1.1- 1 .2(m,5H), 1 .3(m,2H), 2.3(m,1H), 2.6(s,3 H), 4.1 (q,2H), 7.4(d,1H), 7.6(d,1H), 7.9(s,2H), 8.1(s,1H) and ethyl 5-cyclopropyl4-[8-( 1 ,2,3-benztriazol- 1 -yl)- 1,4- benzoxathian-5-oyl]isoxazole-3-carboxylate (Compound 432), NMR 1.1-1.3(m,7H), 2.2(m,1H), 3.1(t,2H), 4.1(q,2H), 4.4(t,2H), 7.2- 7.5(m,5H), 8.1(d,1H).

By proceeding in a similar manner but using 1,2,4-triazole 1- sodium salt and heating at 500C the following compounds were also prepared: ethyl 5-cyclopropyl-4-[3-fluoro-2-methylthio-4-(imidazol-1- yl)benzoyl]isoxazole-3-carboxylate (Compound 116), NMR 1.1 (t,3H), 1.2-1.3(m,4H), 2.4(m,4H), 4.1 (q,2H), 7.1-7.3(m,4H), 7.8(s,1H); ethyl 5-cyclopropyl-4-[3 -methoxy-2-methylthio-4-(imidazol- - yl)benzoyl]isoxazole-3-carboxylate (Compound 433), NMR 1 .2(t,3H), 1.2-1.3(m,4H), 2.3-2.4(m,4H), 3.5(s,3H), 4.0(q,2H), 7.1-7.3(m,4H), 7.8(s,1H) and ethyl 5-cyclopropyl-4-[2-isobutyl-4-(5-methyl- 1 ,2,4-triazol- 1 - yl)benzoyl]isoxazole-3 -carboxylate (Compound 434), NMR 0.9(d,6H), 1.2-1.3(m,7H), 2.0(m,1H), 2.2(m,1H), 2.6(s,3H), 2.8(d,2H), 4.2(q,2H), 7.4(m,2H), 7.5(d,1H), 7.9(s,1H).

Example 2 Hydroxylamine hydrochloride (0.45 g) was added to a stirred solution of 3-cyclopropyl-2-dimethylaminomethylene- 1 - [4-( 1,2,4- triazol-l-yl)-2-trifluoromethylphenyl]propan-1,3-dione in ethanol.

After 2 hours, water was added and the mixture extracted with dichloromethane, washed with water, dried (magnesium sulphate) and evaporated. This residue was purified by chromatography eluting with hexane/ethyl acetate (1:1) to give 5-cyclopropyl-4-[4-(1,2,4-triazol-1- yl)-2-trifluoromethylbenzoyl]isoxazole (Compound 14, 1.56g)as a yellow solid, NMR 1.28(m,2H), 1.38(m,lH), 1.65(m,lH), 7.67(d,lH), 8.03(m,1H), 8.18(m,3H), 8.72(s,1H).

By proceeding in a similar manner the following compounds were also prepared: 5-cyclopropyl-4-[2-(1,2,4-triazol- 1 -yl)benzoyl] isoxazole (Compound 15), NMR 1.20-1.3 5(m,4H), 2.60(m, 1 H), 7.5 5-7.76(m,3H), 7.99(s,1H), 8.07(s,1H), 8.38(s,1H); 5-cyclopropyl-4-[2-(pyrazol-1 -yl)benzoyl]isoxazole (Compound 16), NMR 1.12-1.30(m,4H), 2.70(m,1H), 6.34(m,1H),7.47-7.65(m,4H), 7.71(m,1H), 7.92(s,1H); 5-cyclopropyl-4-[8-( 1 ,2,4-triazol- 1 -yl)- 1 ,4-benzoxathian-5- oyl]isoxazole (Compound 428), NMR 1.1-1.3(m,4H), 2.7(m,1H), 3.0-

3.2(m,2H), 4.6(q,2H), 7.2(d,2H), 7.6(d, 1 H), 8.0(s,1H), 8.2(s,1H), 8.8(s,1H); 5 -cyclopropyl-4- [2-methylthio4-( 1 ,2,4-triazol- 1 - yl)benzoyl]isoxazole (Compound 51), NMR 1.2(m,2H), 1.3(m,2H), 2.5(s,3H), 2.6(m,1H), 7.4(d,1H), 7.5(d,1H), 7.7(s,1 H), 8.1 (s,lH), 8.2(s,1H), 8.6(s,1H); 5-cyclopropyl-4-[2-methyl-4-( 1 ,2,4-triazol- 1 -yl)- benzoyl]isoxazole (Compound 56), NMR l.l(m,2H), 1.3(m,2H), 2.4(s,3H), 2.5(m,1H), 7.4(d,lH), 7.5(d,lH), 7.6(s,lH),8.0(s,1H), 8.2(s,1H), 8.6(s,1H); and 5-cyclopropyl-4- [2-( 1 ,2,4-triazol- 1 -yl)-4- trifluoromethylbenzoyl]isoxazole (Compound 246), NMR 1.2- 1.4(m,4H), 2.6(m,1H), 7.6(d, 1 H), 7:9(m,2H), 8.0(s,2H), 8.5(s,1H).

Example 3 To a suspension of magnesium turnings (0.20g) and methanol was added a catalytic amount of carbon tetrachloride at 200C.The mixture was stirred until dissolved, and a suspension of 3-cyclopropyl- 1 -[2- (1 ,2,4-triazol- 1 -yl)phenyl]propan- 1,3 -dione (1.44g) in methanol was added. The mixture was warmed to 600C, then evaporated and the residue dissolved in toluene. Ethyl chloroximidoacetate (0.91g) was added and the mixture stirred overnight. Aqueous hydrochloric acid was added and the organic layer washed (water), dried (magnesium sulphate), evaporated and the residue purified by chromatography eluting with ethyl acetate/hexane to give ethyl 5-cyclopropyl-4-[2- (1,2,4-triazol- 1 -yl)benzoyl]isoxazole-3 -carboxylate (Compound 17, 1.1 g), NMR 1.20(t.3H), 1 .20(m,2H) , 1 .28(m,2H), 2.33(m,1H), 4.11(q,2H), 7.50-7.77(m,4H), 8.01 (s,1H), 8.41(s,lH).

Example 4 A mixture of 18-crown-6 (1.06g) and 37% w/w potassium fluoride on basic alumina (0.69g) was added portionwise to a mixture of ethyl 5- cyclopropyl-4-(2-fluoro-4-trifluoromethylbenzoyl)isoxazole-3 - carboxylate (1.48g) and 1,2,4-triazole (0.28g) in acetonitrile. The mixture was refluxed for 9.5 hours, evaporated and the residue purified by chromatography, eluting with ethyl acetate/hexane to give ethyl 5- cyclopropyl-4-[2-( 1 ,2,4-triazol- 1 -yl)-4- trifluoromethylbenzoyl]isoxazole-3-carboxylate (Compound 18, 0.77g)

as an orange gum, NMR 1.21(t,3H), 1.25(m,2H), 1.30(m,2H), 2.45(m,1H), 4.12(q,2H), 7.72(d,2H),7.80(d,2H),7.85(s, 1H),8.04(s,lH), 8.46(s,1H).

By proceeding in a similar manner the following compounds were also prepared: ethyl 5-cyclopropyl-4-[2-(1 ,2,3-triazol-1 -yl)-4- trifluoromethylbenzoyl]isoxazole-3-carboxylate (Compound 311), NMR l.l(t,3H), 1.1-1.2(m,4H), 2.4(m,lH), 4.2(q,2H), 7.7(m,4H), 8.2(s,1H); ethyl 5-cyclopropyl-4-[2-( 1,2,3 -triazol-2-yl)-4- trifluoromethylbenzoyl]isoxazole-3-carboxylate (Compound 321), NMR l.l(t,3H), 1.1-1.2(m,4H), 2.3(m,lH), 4.0(q,2H), 7.6(s,1H), 7.7(d,1H), 7.8(d,2H), 7.9(s,1H) and ethyl 5 -cyclopropyl4-[2-( 1,2,3 ,4-tetrazol- 1 -yl)-4- trifluoromethylbenzoyl]isoxazole-3 -carboxylate (Compound 291), NMR 1.2(t,3H), 1.2-1.5(m,4H), 2.4(m,1H), 4.l(q,2H), 7.6(d,1H), 7.8(d,lH), 7.9(s,1H), 9.1(s,1H).

Example 5 m-Chloroperbenzoic acid (0.18g) was added to a stirred solution of ethyl 5-cyclopropyl4- [4-(3 -methylthio- 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]isoxazole-3-carboxylate (0.44g) in dichloromethane at 200C. After 2 hours the mixture was washed with sodium metabisulphite solution and potassium carbonate solution. The organic layer was dried (magnesium sulphate), evaporated and the residue purified by chromatography to give ethyl 5-cyclopropyl-4-[4-(3- methylsulphinyl- l ,2,4-triazol- 1 -yl)-2-trifluoromethylbenzoyl] isoxazole- 3-carboxylate (Compound 19, 0.3g), NMR 1.25(m,2H), 1.40(m,2H), 1.20(t,3H), 2.48(m,1H), 3.13(s,3H), 4.09(q,2H), 7.78(d, 1 H), 8.05(dd,1H), 8.22(s,1H), 8.93(s,1H).

By proceeding in a similar manner the following compounds were also prepared: ethyl 5-cyclopropyl-4-[4-(3 -methylsulfonyl- 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]isoxazole-3-carboxylate (Compound 20), NMR 1.25(m,2H), 1.40(m,2H), 1.20(t,3H), 2.50(m,1H), 3.38(s,3H), 4.09(q,2H), 7.68(d,1H), 8.03(dd,1H), 8.20(d,1H), 8.88(s,1H), 5-cyclopropyl-4-[2-methylsulfinyl-4-( 1 ,2,4-triazol- 1 - yl)benzoyl]isoxazole (Compound 91), NMR 1.2(m,2H), 1.3(m,2H),

2.6(m,1H), 3.0(s,3H), 7.9(d,1H), 8.0(d,1H), 8.1(s,1H), 8.3(s,1H), 8.6(s,lH), 8.8(s,1H); and 5-cyclopropy-4-[2-methylsulfonyl-4-(1,2,4-triazol-1- yl)benzoyl]isoxazole (Compound 92), NMR 1.2(m,2H), 1.3(m,2H), 2.5(m,1H), 3.3(s,3H), 7.6(d,lH), 8. 1(m,3H), 8.4(s,1 H), 8.7(s,1H).

Example 6 A mixture of 5-cyclopropyl-4-[4-( 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]isoxazole (0.3g) and triethylamine (3ml) was stirred in dichloromethane for 1.25 hours, washed with citric acid and the organic phase dried (magnesium sulphate) and evaporated to give 2- cyano-3-cyclopropyl- 1 -[4-( 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylphenyl]propan-1,3-dione as an orange solid (Compound 49, 0.24g), NMR 1 .33(m,2H),1 .50(m,2H), 1 .38(m, 1 H),7.78(d,1H), 8.05(m,1H), 8.20(m,2H), 8.85(m,1H).

Example 7 Sodium methoxide (17mg) followed by sodium hydroxide (2M solution) was added to a solution of 5-cyclopropyl-4-[2-(1,2,4-triazol-1- yl)-4-trifluoromethylbenzoyl]isoxazole (0.1 g), stirred overnight, acidified (2M hydrochloric acid) and extracted (dichloromethane). The extract was dried (magnesium sulphate) and evaporated to give 2-cyano- <BR> <BR> 3-cyclopropyl- 1 -[2-(1,2,4-triazol- 1 -yl)4-trifluoromethylphenyl]propan- 1,3-dione (Compound 424), NMR 1.2(m,2H), 1.3(m,2H), 2.1(m,1H), 7.7(m,3H), 8.0(s,1H), 8.5(s,lH), 1 5(bs,1 H).

Example 8 To a solution of 1,3-dimethyl-5-[4-(1,2,4-triazol.1-yl)-2- <BR> <BR> trifluoromethylbenzoyloxy]-1H-pyrazole (1.93g) in in t-amyl alcohol was added a catalytic amount of 1 ,3-dimethyl-5-hydroxy- 1 H-pyrazole and potassium carbonate (0.76g) at 200C. The reaction mixture was warmed to 1000C, stirred for 4 hours and cooled. After extraction with ether the aqueous layer was acidified (aqueous citric acid), extracted (dichloromethane), dried (magnesium sulfate) and evaporated to give 1 ,3-dimethyl-5.hydroxy4-[4-( 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]-lH-pyrazole as an orange glassy solid (Compound 501, 1.85g), NMR 1.70(s,3H), 3.65(s,3H), 7.69(1H), 8.00(1H), 8.15(1H), 8.18(s,1H), 8.71(s,1H). By proceeding in a similar manner the following compounds were also prepared:

5-hydroxy-1-methyl-4-[4-1,2,4-triazol-1-yl)-2- trifluoromethylbenzoy1]- 1H-pyrazole (Compound 517), NMR 3.73(3H,s), 7.33(1H,s), 7.73(1H,d), 8.00(1H,d), 8.18(2H), 8.71(1H); and 1,3-dimethyl-5-hydroxy-4-[4-(1,2,4-triazol- 1 -yl)-2- chlorobenzoyl]-lH-pyrazole (Compound 1116), NMR 1.82 (s, 3H), 3.65 (s,3H), 7.47 (d, 1H), 7.76 (d, 1H), 7.90 (d, 1H), 8.16 (s, 1H), 8.67 (s, 1H).

Example 9 To a solution of 1,3-dimethyl-5-hydroxy-4-[4-(1,2,4-triazol-1-yl)- 2-trifluoromethylbenzoyl]- 1 H-pyrazole (0.35g) in N,N- dimethylformamide was added phenacyl chloride (0.17g) and potassium carbonate (0.15g) at 200C. The mixture was stirred for 4 hours, diluted with ether and washed with water. The organic layer was dried (magnesium sulfate), evaporated and the residue purified by chromatography to give 1,3-dimethyl-5-phenacyloxy-4-[4-(1,2,4-triazol- 1 -yl)-2-trifluoromethylbenzoyl] 1 H-pyrazole (Compound 502, 0.37g), NMR 1.74(s,3H), 3.86(s,3H), 5.85(s,2H), 7.45-7.65(4H), 7.80-7.98(3H), 8.10(1H), 8.16(s,1H), 8.68(s,lH).

By proceeding in a similar manner the following compounds were also prepared: 1,3-dimethyl-5-methoxy-4-[4-(1,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl] 1 H-pyrazole (Compound 503), NMR <BR> <BR> 2.03(s,3H),3.65(s,3H),3.83(s,3H),7.60(1 H),7.96(l H),8. 12(1 H),8. 1 7(s,1 H),8.70(s,1H); 5 -ethoxy- 1 ,3-dimethyl-4-[4-( 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl] 1 H-pyrazole (Compound 504), NMR <BR> <BR> 1.18(t,3H),2.04(s,3H),3.62(s,3H),4.07(q,2H),7.60(1 H),7.95(1 H),8.13(1 <BR> <BR> <BR> <BR> <BR> <BR> H),8.18(s,1H),8.70(s,lH); 1,3-dimethyl-5-isopropyloxy-4-[4-(1,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoy1]- 1H-pyrazole (Compound 505), NMR 1.19(d,6H),1.99(s,3H),3.65(s,3H),4.60(sep,1H),7.59(1H),7.95( 1H),8.14( lH),8.17(s,1H),8.69(s,1H); 5-benzyloxy- 1,3-dimethyl-4-[4-(1,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoy1]- 1H-pyrazole (Compound 506), NMR 2.02(s,3H),3.43(s,3H), 5.08(s,2H),7.15- 7.32(5H),7.53(1H),7.90(1H),8.08(1H),8.17(s,1H),8.64(s,1H);

1,3-dimethyl-5-methoxycarbonylmethoxy-4-[4-(1,2,4-triazol-1- yl)-2-trifluoromthylbenzoyl]-1H-pyrazole (Compound 507), NMR 1.75(s,3H),3.77(s,3H),3.79(s,3H),5.03(s,2H),7.54(1H),7.98(1H ),8.13(1 H),8.17(s,1H),8.71(s,lH); 1,3-dimethyl-5-[1-(methoxycarbonyl)ethoxy]-4-[4-(1,2,4-triaz ol- l-yl)-2-trifluoromethylbenzoyl]-1H-pyrazole (Compound 508), NMR 1.65(d,3H),1.72(s,3H),3.74(s,3H),3.78(s,3H),5.41(q,1H),7.52( 1H),7.97( lH),8.13(1H),8.17(s,1H),8.71(s,1H); 1,3-dimethyl-5-allyloxy-4-[4-(1,2,4-triazol-1-yl)-2- trifluoromethylbenzoy1]- 1H-pyrazole (Compound 509), NMR 2.01(s,3H),3 .65(s,3H),4.56(d,2H),5.20-5 .30(m,2H),5.65- 5.90(m,1H),7.58(1H),7.96(1H),8.12(1H),8.17(s,1H),8.71(s,1H) 1,3-dimethyl-5-propargyloxy-4-[4-(1,2,4-triazol-1-yl)-2- trifluoromethylbenzoyl]-lH-pyrazole (Compound 510), NMR 1.88(s,3H),2.56(m,1H),3.73(s,1H),4.91(d,1H),7.58(1H),7.97(1H ),8.14(1 H),8.17(s,1H),8.71(s,1H); 1,3-dimethyl-5-methoxy-4-[2-chloro-4-(1,2,4-triazol-1- yl)benzoyl]-lH-pyrazole (Compound 1125), NMR 2.09 (s, 3H), 3.65 (s, 3H), 3.85 (s, 3H), 7.52 (d, 1H), 7.70 (d, 1H), 7.87 (s, lH), 8.15 (s, 1H), 8.65 (s, 1H); 1,3-dimethyl-5-phenacyloxy-4-[2-chloro-4-(1,2,4-triazol-1- yl)benzoyl]-lH-pyrazole (Compound 1126), NMR 1.83 (s, 3H), 3.85 (s, 3H), 5.85(s, 2H), 7.38-7.52 (m, 3H), 7.55-7.73 (m, 2H), 7.79-7.92 (m, 3H), 8.13 (s, 1H), 8.60 (s, 1H); 1 ,3-dimethyl-5-benzyloxy-4-[2-chloro-4-( 1,2,4-triazol-l- yl)benzoyl]-lH-pyrazole (Compound 1127), NMR 2.10 (s, 3H), 3.43 (s, 3H), 5.06 (s, 2H), 7.17-7.34 (m, 5H), 7.50 (d, 1H), 7.66 (d, 1H), 7.81 (s, 1H), 8.15 (s, 1H), 8.58 (s, 1H); 1,3,-dimethyl-5-propargyloxy-4-[2-chloro-4-(1,2,4-triazol-1- yl)benzoyl]-lH-pyrazole (Compound 1128), NMR 1.99 (s, 3H), 2.55 (s, 1H), 3.73 (s, 3H), 4.88 (s, 2H), 7.51 (d, 1H), 7.70 (d, 1H), 7.87 (s, 1H), 8.15 (s,lH), 8.64 (s, 1H); 1,3-dimethyl-5-allyloxy-4-[2-chloro-4-(1,2,4-triazol- 1 - yl)benzoyl]-lH-pyrazole (Compound 1129), NMR 2.08 (s, 3H), 3.65 (s, 3H), 4.56 (s, 3H), 5.19-5.34 (m, 2H), 5.82 (m, 1H), 7.51 (d, 1H), 7.69 (d, 1H), 7.99 (s, 1H), 8.17 (s, 1H), 8.63 (s, 1H);

1-methyl-5-benzyloxy-4-[4-(1,2,4-triazol-1-yl)-2- trifluoromethylbenzoy1]-1 H-pyrazole (Compound 1131), NMR 3.52 (s, 3H), 5.58 (s, 2H), 7.24 (s, 1H), 7.59 (d, 1H), 7.94 (d, 1H), 8.14 (s, 1H), 8.18 (s, 1H), 8.69 (s, 1H); and 1 -methyl-5-allyloxy-4-[4-(1,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]-lH-pyrazole (Compound 1132), NMR 3.72 (s, 3H), 5.08 (d, 2H), 5.31 (dd, 1H), 5.41 (dd, 1H), 6.03 (m, 1H), 7.25 (d, 1H), 7.60 (d, 1H), 7.95 (dd, 1H), 8.11-8.20 (m, 2H), 8.70 (s, 1H).

Example 10 To a solution of 1,3-dimethyl-5-hydroxy-4-[4-(1,2,4-triazol-1-yl)- 2-trifluoromethylbenzoyl]-lH-pyrazole (0.1g) in dichloromethane was added benzenesulfonyl chloride (0.06g) and triethylamine (0.04g) at 200C. The mixture was stirred for 4 hours, extracted with ether and washed with water. The organic layer was dried (magnesium sulfate), evaporated and the residue purified by chromatography to give 5- benzenesulfonyloxy- l ,3-dimethyl-4-[4-(1,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]-1H-pyrazole (Compound 511, 0.05g), NMR 2.17(s,3H),3.59(s,1H),7.52(3H),7.66(1H),7.83(3H),8.05(1H), 8.19(s,1H). 8.67(s,lH).

By proceeding in a similar manner the following compounds were also prepared: 5-acetyloxy-1,3-dimethyl-4-[4-(1,2,4-triazol-1-yl)-2- trifluoromethylbenzoyl]-1H-pyrazole (Compound 512), NMR 2.06(s,3H),2.16(s,3H),3.63(s,3H),7.52(1H),7.98(1H),8.13(1H), 8.17(s,1 H),8.70(s,1H); 5-benzoyloxy- 1,3-dimethyl-4-[4-(1,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]-1H-pyrazole (Compound 513), NMR <BR> <BR> 2.51(s,3H),3.64(s,3H),7.25(2H),7.40(2H),7.55(1H),7.70(2H),7. 78(1H),8 <BR> <BR> <BR> <BR> <BR> .06(s,1H),8.22(s,1H); 1,3 -dimethyl-5-pivaloyloxy4 [4-( 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl] 1 H-pyrazole (Compound 514), NMR <BR> <BR> 1.1 8(s,9H),2.14(s,3H),3.60(s,3H),7.55(1H),7.92(1H),8. 1 0(1H),8. 1 7(s,1 H),8.67(s,1H); 1,3 -dimethyl-5-p-toluenesulfonyloxy4-[4-( 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoy1]- 1H-pyrazole (Compound 515), NMR

2.21(s,3H),2.41 (s,3H),3.58(s,3H),7.28(2H),7.52(1 H),7.70(2H), 7.75(1H), 8.04(1H), 8.19(s,1H), 8.67(s,lH); 1,3 ,3-dimethyl-5-isopropylaulfonyloxy-4- [4-( 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]- 1 H-pyrazole (Compound 516), NMR a.57(d,6H),1.88(s,3H),3.84(s,3H),3.85(sep,1H),7.62(1H),7.98( 1H),8.15( 1H),8.18(s,1H),8.72(s,1H); 1 -methyl-5-benzoyloxy-4-[4-(1,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]-1H-pyrazole (Compound 1117), NMR 3.77 (s, 3H), 7.30-7.46 (m, 2H), 7.49-7.60 (m, 2H), 7.74 (dd, 1H), 7.82 (s, 1H), 7.90-8.00 (m, 3H), 8.11 (s, 1H), 8.46 (s, 1H); 1 -methyl-5 -pivaloyloxy-4- [4-( 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]-lH-pyrazole (Compound 1118), NMR 1.40 (s, 9H), 3.72 (s, 3H), 7.47 (s, 1H), 7.63 (d, 1H), 7.95 (d, 1H), 8.12 (s, 1H), 8.17 (s, 1H), 8.70 (s, 1H); 1 -methyl-5 -benzenesulfonyloxy-4- [4-( 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]-1H-pyrazole (Compound 1119), NMR 3.85 (s, 3H), 7.40-7.80 (m, 5H), 7.85-8.25 (m, 5H), 8.69 (s, 1H); 1 -methyl-5-p-toluenesulfonyloxy-4-[4-(1,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]-1H-pyrazole (Compound 1120), NMR 2.45 (s, 3H), 3.84 (s, 3H), 7.36 (s, 1H), 7.39 (s, 1H), 7.47-7.50 (m, 2H), 7.85- 7.95 (m, 3H), 8.08 (d, 1H), 8.18 (s, 1H), 8.69 (s, 1H); 1,3-dimethyl-5-acetoxy-4-[2-chloro-4-(1,2,4-triazol-1- yl)benzoyl]-lH-pyrazole (Compound 1121), NMR 2.07 (s, 3H), 3.63 (s, 3H), 7.44 (d, 1H), 7.68 (d, 1H), 8.87 (s, 1H), 8.14 (s, 1H), 8.64 (s, 1H); 1,3-dimethyl-5-pivaloyloxy-[2-chloro-4-(1,2,4-triazol-1- yl)benzoyl]-lH-pyrazole (Compound 1122), NMR 1.24 (s, 9H), 2.17 (s, 3H), 3.61 (s, 3H), 7.48 (d, 1H), 7.65 (d, 1H),7.84 (s, 1H), 8.14 (s, 1H), 8.62 (s, 1H); 1,3-dimethyl-5-benzensulfonyloxy-4-[2-chloro-4-(1,2,4-triazo l- l-yl)benzoyl]-lH-pyrazole (Compound 1123), NMR 2.29 (s, 3H), 3.55 (s, 3H), 7.25-7.90 (m, 8H), 8.16 (s, 1H), 8.62 (s, 1H); 1,3 ,3-dimethyl-5-p-toluenesulfonyloxy-4- [4-( 1,2 ,4-triazol- 1 -yl)-2- chlorobenzoyl]-lH-pyrazole (Compound 546), NMR 2.32 (s, 3H), 2.41 (s, 3H), 3.54 (s, 3H), 7.23-7.32 (m, 2H), 7.46 (d, 1H), 7.55-7.65 (m, 3H), 7.75 (s, 1H), 8.16 (s, 1H), 8.63 (s, 1H);

1,3 -dimethyl-5 -isopropylsulfonyloxy-4- [2-chloro-4-(1,2,4-triazol- l-yl)benzoyl]-lH-pyrazole(Compound 1124), NMR 1.66 (d, 6H), 2.02 (s, 3H), 3.78 (heptet, 1H), 3.92 (s, 3H), 7.56 (s, 1H), 7.70 (d, 1H), 7.87 (d, 1H), 8.15 (s, 1H), 8.66 (s, 1H); and 1 -methyl-5-acetoxy-4-[4-(1,2,4-triazol- 1 -yl)-2- trifluoromethylbenzoyl]-1H-pyrazole (Compound 1130), NMR 2.40 (s, 3H), 3.75 (s, 3H), 7.48 (s, 3H), 7.63 (d, 1H), 7.96 (d, 1H), 8.14 (s, 1H), 8.17 (s, 1H), 8.70 (s, 1H).

Reference Example 1 A mixture of magnesium turnings (1.12g) and methanol was heated under reflux until dissolved, then a solution of 3-cyclopropyl- 1 - (4-fluoro-3-trifluoromethylphenyl)propan 1 ,3-dione (11 .5g) in methanol added at 200C. Acetonitrile was added and the mixture heated under reflux for four hours, evaporated and dissolved in dichloromethane. A solution of ethyl chloroximidoacetate (6.72g) in dichloromethane was added and the mixture stirred overnight. Hydrochloric acid (2M) was added and the organic layer was washed with water, dried (magnesium sulphate), evaporated and the residue purified by chromatography eluting with ethyl acetate/hexane to give ethyl 5-cyclopropyl-4-(4- fluoro-2-trifluoromethylbenzoyl)isoxazole-3 -carboxylate as a colourless solid (11.75g), NMR 1.05-1.3(m,4H), 1.2(t,3H), 2.1 (m,1 H), 2.38(s,3H), 4.17(q,2H), 4.3(s,2H), 6.72(d, 1 H), 6.86(m,1H), 7.06(m,2H), 7.2(m,2H), 7.45(m,1 H).

By proceeding in a similar manner the following compounds were also prepared: ethyl 5-cyclopropyl4-(4-fluoro-2-methylbenzoyl)isoxazole-3 carboxylate, NMR 1.13-1.35(m,4H), 1.69(t,3H), 2.30(m,1H), 4.10(q,2H), 6.78-7.05(m,2H), 7.40(m, 1 H); ethyl 5-cyclopropyl-4-(2-chloro4-fluorobenzoyl)isoxazole-3- carboxylate, NMR 1.22(m,2H), 1.35(m,2H), 1.22(t,2H), 2.40(m,1H), 4.14(q,2H), 7.08(m,1H),7.20(m,1H), 7.53(m,1H); ethyl 5-cyclopropyl4-(4-fluoro-2-iodobenzoyl)isoxazole-3- carboxylate, NMR 1 .22(m,2H), 1.3 5(m,2H), 1 .22(t,3H), 2.3 5(m, 1 H), 4.14(q,2H), 7.1 5(m,1H), 7.40(m,1H), 7.70(m,1H);

ethyl 5-cyclopropyl4-(4-fluoronaphthoyl)isoxazole-3 carboxylate, NMR 1.13-1.38(m,4H), 0.88(t,3H), 2.32(m,1H), 3.90(q,2H), 7. 12(m,1H), 7.59(m,3H), 8.20(d,1H),8.68(d,1H); ethyl 5-cyclopropyl-4- [(2-fluoro-4- trifluoromethyl)benzoyl]isoxazole-3 -carboxylate, NMR 1.27(m,2H), 1 .35(m,2H), 1.1 8(t,3H), 2.49(m,1H), 4.1 6(q,2H), 7.39(d, 1 H), 7.55(d,1H), 7.90(t,1H); ethyl 5-cyclopropyl-4-[(2-benzyl-4-fluoro)benzoyl]isoxazole-3- carboxylate, NMR 1.20(m,2H), 1.25(m,2H), 1.20(t,3H), 2.00(m,1H), 4.15(q,2H), 4.27(s,2H), 6.93(m,2H), 7.15-7.35(m,5H), 7.42(m,1H); ethyl 4-(2-isobutyl-4-fluorobenzoyl)-5-cyclopropyl-isoxazole-3- carboxylate, NMR 0.92(d,6H), 1.15(m,2H), 1.21(t,3H), 1.29(m,2H), 1.95(sep,7H), 2.72(d,2H), 4.17(q,2H), 6.89-7.03(m,2H), 7.42(m,1H); ethyl 4-(3 ,4-difluoro-2-methylthiobenzoyl)-5 -cyclopropyl- isoxazole-3-carboxylate, NMR 1.2(t,3H), 1.22(m,2H), 1.39(m,2H), 2.41 (m, 1 H), 2.5(s,3H), 4.19(q,2H), 7.1-7.22(m,2H); ethyl 4-(3 -bromo-4-fluoro-2-methylthiobenzoyl)-5 -cyclopropyl- isoxazole-3-carboxylate, NMR 1.21(m,2H), 1.25(t,3H), 1.32(m,2H), 2.4(m,1H), 2.41(s,3H), 4.18(q,2H), 7. 12(t,1H), 7.35(dd,1H); ethyl 4-(2-ethyl-4-fluoro-3-methylthiobenzoyl)-5-cyclopropyl- isoxazole-3-carboxylate, NMR 1.1 - 1.4 (m,4H), 1.1 (t,3H) , 1.2 (t,3H), 2.2 (m,lH), 2.4 (s,3H) , 3.1 (q,2H) , 4.1 (q,2H) , 6.9 (t,lH), 7.3 (m,lH); ethyl 4-(4-fluoro-3-methoxy-2-methylthiobenzoyl)-5-cyclopropyl- isoxazole-3-carboxylate, NMR 1.18(m,2H), 1.22(t,3H), 1.28(m,2H), 2.32(m,1H), 2.42(s,3H), 4.03(s,3H), 4.15(q,2H), 7.09(d,1H), 7.1 l(s,1H); ethyl 4-(4-fluoro-2-methylthiomethylbenzoyl)-5-cyclopropyl- isoxazole-3-carboxylate, NMR 1.16(m,2H), 1.71 (t,3H), 1.78(m,2H), 2.06(s,3H), 2.1 8(m, 1 H), 4.02(s,2H), 4.19(q,2H), 6.98(m,1H), 7.25(dd,1H), 7.47(dd,1H); and ethyl 5-cyclopropyl4- [8-fluoro- 1 ,4-benzoxathian-5-oyl]isoxazole- 3-carboxylate, NMR 1.1 -1.2(m,5H), 1.3(m,2H), 2.2(m,1H), 3.1 (t,2H), 4.2(q,2H), 4.5(t,2H), 6.8(m,1H), 7.1(m,1H).

Reference Example 2 To a stirred solution of 3-cyclopropyl-1-[4-fluoro-2,3-bis- (methylthio)phenyl]-propan- 1 ,3-dione in dry toluene was added ethyl cyanoformate (0.35g) and zinc acetate (0.015g). The mixture was stirred

at 900C for 1.5 hours, then allowed to cool. Hydroxylamine hydrochloride (0.3g) and sodium acetate (0.055g) was added and the mixture stirred at 600C for 1 hour. Water was added and the mixture extracted (ether), dried (magnesium sulphate)and evaporated to give ethyl 4-[4-fluoro-2,3-bis-(methylthio)-benzoyl]-5-cyclopropylisoxa zole- 3-carboxylate as a yellow oil, NMR 1.2 (t,3H), 1.1 - 1.4 (m,4H) , 2.3 (m,1H) , 2.4 (s,3H) , 2.6 (s,3H) , 4.1 (q,2H), 7.1 (m,lH), (m,2H).

Reference Example 3 Oxalyl chloride (6.5ml) and a catalytic amount of N,N- dimethylformamide was added to a suspension of 4-fluoro-2- trifluoromethylbenzoic acid (10.0g) in dry dichloromethane. The mixture was stirred to give a clear solution. Meanwhile a solution of t- butyl 3-cyclopropyl-3-oxopropionate (12.33g) in methanol was added to a stirred mixture of magnesium turnings (1.40g) in methanol. The mixture was heated at 600C for 0.75 hours, cooled and evaporated.

Toluene was added and the mixture was re-evaporated. The residue was redissolved in toluene and the above solution of 4-fluoro-2- trifluoromethylbenzoyl chloride (9.19g) added. The mixture was stirred at 200C for 24 hours, then hydrochloric acid (2M) added and the stirring continued for a further 1 hour. The organic phase was washed with hydrochloric acid (2 M) and water, dried (magnesium sulphate) and 4- toluenesulphonic acid (0.5g) and toluene were added. The mixture was stirred at reflux for 2 hours, cooled and washed in turn with saturated sodium bicarbonate solution and water, dried (magnesium sulphate) and evaporated to give 3-cyclopropyl-l-(4-fluoro-2- trifluoromethylphenyl)propan- 1 ,3-dione (11.50g) as a red oil, NMR 1.0(m,2H), 1.2(m,2H), 1 .7(m, 1 H), 5.8(s,1H), 7.2-7.6(m,3H).

By proceeding in a similar manner the following compounds were also prepared: 3-cyclopropyl- 1 -(2-fluoro-4-trifluoromethylphenyl)propan- 1,3- dione, NMR 1.0(m,2H), 1.22(m,2H), 6.43(s,lH),7.38(dd, lH),7.48(d,1H), 8.08(m,1H); 3-cyclopropyl- 1 -(4-fluoro-2-iodophenyl)propan- 1 ,3-dione, NMR 1.05(m,2H), 1.25(m,2H), 1 .78(m,1H), 5.95(s,1H), 7. 12(m,1H), 7.43(m,1H), 7.65(m,1H);

3 -cyclopropyl- 1 -(4-fluoro-2-methylphenyl)propan- 1,3 -dione, NMR 0.98(m,2H), 1.20(m,2H), 1.75(m,1H), 2.50(s,3H), 5.90(s,1H), 6.92(m,2H),7.48(m,1H); 1 -(2-chioro-4-fluorophenyl)-3-cyclopropylpropan- 1,3 -dione, NMR 1.02(m,2H), 1.22(m,2H), 1.68(m,1H), 6.15(s,1H), 7.05(m,1H), 7.20(m,1H), 7.65(m,1H); l-(2-benzyl-4-fluorophenyl)-3-cyclopropylpropan-1,3-dione, NMR 0.98(m,2H), 1.16(m,2H), 1.68(m,1H), 4.20(s,2H), 5.82(s,1H), 6.80-7.50(m,8H); 3-cyclopropyl- 1 -(4-fluoro-3 -methoxy-2-methylthiophenyl)propan- 1,3-dione, NMR 0.98(m,2H), 1.31(m,2H), 1.82(m,1H), 2.41(s,3H), 4.05(s,3H), 6.02(s,1H), 7.10-7.40(m,2H), 1 6.0(bs,1H); 3-cyclopropyl- 1 -(4-fluoro-2-isobutylphenyl)propan- 1,3 -dione, NMR 0.87(d,6H), 0.98(m,2H), 1.31(m,2H), 1.74(m,1H), 1.85(m,1H), 2.72(d,2H), 5.88(s,1H), 6.90-6.99(m,2H), 7.41 (q,1 H); 1 -(3-bromo-4-fluoro-2-methylthiophenyl)-3-cyclopropylpropan- 1 ,3-dione, NMR 1.01 (m,2H), 1.23(m,2H), 1.76(m,1H), 2.45(s,3H), 5.97(s,1H), 7.10-7.40(m,2H); 3 -cyclopropyl- 1 -(3,4-difluoro-2-methylthiophenyl)propan- 1,3 - dione, NMR 0.98(m,2H), 1.25(m,2H), 1.75(m,lH), 2.52(s,3H), 6.02(s,1H), 7.10-7.40(m,2H); 3-cyclopropyl- 1 -[2,3-bis-(methylthio)-4-fluorophenyl]propan- 1,3- dione, NMR 0.98(m,2H), 1.25(m,2H), 1.82(m,lH), 2.42 (s,3H), 2.51 (s,3H), 5.95(s,1H), 7.09(t,lH), 7.32(q, lH); 3-cyclopropyl- 1 -(4-fluoro- 1 -naphthyl)propan- 1,3 -dione; 3-cyclopropyl-1-(2-ethyl-4-fluoro-3-methylthiophenyl)propan- 1,3- dione, as an orange oil, NMR 0.95(m,2H), 1.15(m,2H), 1.7(m,1H), 2.4(s,3H), 3.05(q,2H), 5.85(s,1H), 7.0(t,1H), 7.3(t,1H), 1 6.0(bs,1H); 3-cyclopropyl-1-[8(1,2,4-triazol-1-yl)-1,4-benzoxathian-5- yl]propan- 1 ,3-dione, NMR 0.9(m,2H), 1.1 (m,2H), 1 .6(m, 1 H), 3 .0(t,2H), 4.5(t,2H), 6.0(s,1H), 7.2(d,1H), 7.5(d,1H), 8.0(s, 1H), 8.7(s, 1H), 15.9(bs,1H); 3-cyclopropyl- 1 - [2-methylthio-4-(1,2,4-triazol- 1 - yl)phenyl]propan-1,3-dione, NMR 0.9(m,2H), 1.2(m,2H), 1.7(m,1H), 2.5(s,3H), 6. 1(s,1H), 7.3(d,1H), 7.6(m,2H), 8.1 (s, 1H), 8.6(s,1H), 1 6.0(bs, 1H);

3 -cyclopropyl- 1 -[2-methyl4-( 1 ,2,4-triazol- 1 -yl)phenyl]propan- <BR> <BR> 1 ,3-dione; <BR> <BR> <BR> <BR> <BR> <BR> 3 -cyclopropyl- 1 -[2-(1,2,4-triazol- 1 -yl)-4- trifluoromethylphenyl]propan- 1,3-dione, NMR 0.9(m,2H), 1.1 (m,.2H), 1 .5(m,1H), 3.7(s,1H), 5.5(s,1H), 7.1(d,1H), 7.2(m,1H), 7.7(m,1H), 8.1(s,1H), 8.3(s,1H); and 3-cyclopropyl-1-[8-fluoro-1,4-benzoxathian-5-yl]propan-1,3- dione, NMR 1.2(m,2H), 1.4(m,2H), 1.7(m,1H), 3.0(t,2H), 4.5(t,2H), 6.0(s,lH), 6.8(m,1H), 7. 1-7.3(m,1H), 1 6.0(bs,1H).

Reference Example 4 A mixture of 3-cyclopropyl- 1 -[4-( 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylphenyl]propan- 1,3-dione (1.56g) and N,N- dimethylformamide-dimethylacetal (5 ml) in toluene was heated at 800C for 3 hours. The mixture was then evaporated to give 3- cyclopropyl-2-dimethylaminomethylene- 1 - [4-( 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylphenyl]propan-1,3-dione . This was used directly in the next stage.

By proceeding in a similar manner the following compounds were also prepared: <BR> <BR> <BR> 3-cyclopropyl-2-dimethylaminomethylene- 1 - [2-( 1,2 ,4-triazol- 1 - <BR> <BR> <BR> <BR> <BR> <BR> yl)phenyl]propan 1 ,3-dione; <BR> <BR> <BR> <BR> <BR> <BR> 3-cyclopropyl-2.dimethylaminomethylene- 1- [2-(pyrazol- 1 - <BR> <BR> <BR> <BR> <BR> <BR> yl)phenyl]propan- 1 ,3-dione; 3-cyclopropyl-2-dimethylaminomethylene-1-[8-(1,2,4-triazol-1 - yl)- 1 ,4-benzoxathian-5-yl]propan- 1 ,3-dione; 3 -cyclopropyl-2-dimethylaminomethylene 1 - [2-methylthio-4- (1 ,2,4-triazol- 1 -yl)phenyl]propan- 1 ,3-dione; 3-cyclopropyl-2-dimethylaminomethylene -1 -[2-methyl-4-(1 ,2,4- triazol- 1 -yl)phenyl]propan 1 ,3-dione; and 3-cyclopropyl-2-dimethylaminomethylene 1 - [2-( 1 ,2,4-triazol- 1 - yl)-4-trifluoromethylphenyl]propan- 1,3 -dione.

Reference Example 5 A solution of methyl [4-(1,2,4-triazol-1 -yl)-2- trifluoromethyl]benzoate(1.73g) and methyl cyclopropyl ketone (1 .07g) in tetrahydrofuran (10ml) was added dropwise to a suspension of sodium hydride (60% dispersion in mineral oil, 0.55g) in

tetrahydrofuran at 600C. The mixture was refluxed for 2 hours and then cooled to 200C. Ether and dilute citric acid were added and the organic layer washed (water), dried (magnesium sulfate) and evaporated. The residue was purified by chromatography eluting with ethyl acetate/hexane to give 3 -cyclopropyl- 1 -[4-( 1 ,2,4-triazol- 1 -yl)-2- trifluoromethylphenyl]propan- 1,3 -dione.

By proceeding in a similar manner the following compounds were also prepared: 3 -cyclopropyl- 1 -[2-( 1 ,2,4-triazol- 1 -yl)phenyl]propan- 1,3 -dione, NMR 0.95(m,2H), 1.10(m,1H),1.60(m,1H), 5.51 (s,lH), 7.50- 7.78(m,4H), 8.12(s,1H), 8.30(s,1H); 3-cyclopropyl- 1 -[2-(pyrazol- 1 -yl)phenyl]propan- 1,3 -dione, NMR 0.90(m,2H), 1.05(m,2H), 1.52(m,1H), 5.28(s,lH), 6.40-6.52(m,2H), 7.41-85(m,5H); and 3 -cyclopropyl- 1 - [4-fluoro-2-methylthiomethylphenyljpropan- 1,3 - dione, NMR 1.05(m,2H), 1.25(m,lH),1.65(m,l H), 2.06(s,3H), 3.98(s,2H), 6.02(s,lH), 6.95-7.43(m,3H), 16.20(br.s,1H).

Reference Example 6 To a solution of methyl 4-fluoro-2-trifluoromethylbenzoate (4.95g) in N,N-dimethylformamide was added 1,2,4-triazole (2.0g) and potassium carbonate (4.0g) at 200C and the mixture stirred for 4 hours at 600C. The mixture was diluted (ether), washed (aqueous citric acid) and dried (magnesium sulfate). The residue was purified by chromatography to give methyl 4-(1,2,4-triazol-1-yl)-2- trifluoromethylbenzoate (5.07g), NMR 3.98(s,3H),7.94- 8.05(2H),8.15(2H),8.71(s,1H).

By proceeding in a similar manner the following compounds were also prepared: methyl 8-( 1 ,2,4-triazol- 1 -yl)- 1 ,4-benzoxathian-5 -carboxylate, NMR 3.2(t,2H), 3.9(s,3H), 4.5(t,2H), 7.6(d,1H), 7.8(d,1H), 8.l(s,1H), 8.8(s,1H).

By proceeding in a similar manner but using 1,2,4-triazole 1 - sodium salt the following compounds were also prepared: methyl 2-methylthio-4-(l ,2,4-triazol-l -yl)benzoate, mp 155- 1560C; methyl 2-methyl4-( 1 ,2,4-triazol- 1 -yl)benzoate, mp 106-1 070C.

Reference Example 7 A solution of lithium hydroxide monohydrate (0.1 6g) in water was added to a solution of methyl 8-(1,2,4-triazol-1-yl)-1,4-benzoxathian-5- carboxylate (0.36g) in methanol and stirred at 200C for 18 hours. The mixture was evaporated, diluted (water), washed (ether) and acidified with hydrochloric acid to give 8-(1,2,4-triazol-1-yl)-1,4-benzoxathian-5- carboxylic acid (0.32g), mp3 03-3 050C.

By proceeding in a similar manner but using potassium hydroxide as base the following compounds were also prepared: 2-methylthio-4-(1,2,4-triazol-1-yl)benzoic acid, NMR 2.5(s,3H), 7.7(m,2H), 8.0(d,lH), 8.3(s,lH), 9.5(s,lH), 13.2(bs,lH); 2-methyl-4-(1,2,4-triazol-1-yl)benzoic acid, NMR 2.6(s,3H), 7.8(d,lH), 7.9(s,1H), 8.0(d,lH), 8.3(s,lH), 9.4(s, 1 H), 13.0(bs,lH); 2-(1,2,4-triazol-1-yl)-4-trifluoromethylbenzoic acid, NMR 7.9- 8.1 (m,3H), 8.2(s,lH), 9.0(s,1H), 1 3.6(bs,l H); and 8-fluoro-l ,4-benzoxathian-5-carboxylic acid, NMR 3.0(t,2H), 4.4(t,2H), 6.8(m,lH), 7.6(m,lH).

Reference Example 8 A solution of methyl 3-(2-chloroethoxy)-4-fluoro-2- methylthiobenzoate (3.46g) in N,N-dimethylformamide was heated at 1 400C for 18 hours, cooled, diluted (water) and extracted (ether). The extract was washed (water), dried (magnesium sulphate) and evaporated to give methyl 8-fluoro-l,4-benzoxathian-5.carboxylate (2.96g), NMR 3.1(t,2H), 3.9(s,3H), 4.5(t,2H), 6.8(m,lH), 7.6(m,lH).

By proceeding in a similar manner the following compounds were also prepared: ethyl 8-fluoro- 1 ,4-benzoxathian-5-carboxylate, NMR 1.4(t,3H), 3.l(m,2H), 4.3(q,2H), 4.5(m,2H), 6.8(m,1H), 7.6(m,1H).

Reference Example 9 A mixture of methyl 4-fluoro-3-hydroxy-2-methylthiobenzoate (3.06g), 2-bromo-1-chloroethane (1.3ml) and potassium carbonate (2.15g) was stirred in dry acetonitrile at reflux for 18 hours, cooled, diluted (water), brought to pH1 1 with sodium hydroxide (2M) and extracted (ether). The organic phase was washed (water), dried (magnesium sulphate) and evaporated to give methyl 3-(2-

chloroethoxy)-4-fluoro-2-methylthiobenzoate (3.46g), used directly in the next stage.

By proceeding in a similar manner the following compound was also prepared: ethyl 3-(2-chloroethoxy)-2,4-difluorobenzoate, NMR 1.4(t,3H), 3.8(m,2H), 4.3-4.4(m,4H), 6.9(m, 1 H), 7.7(m,1H).

Reference Example 10 A mixture of ethyl 3-(2-chloroethoxy)-2,4-difluorobenzoate (54.5g), and sodium methoxide (15.9g) in dry tetrahydrofuran was stirred at 200C for 2 days under nitrogen, evaporated and mixed with ether and water. The organic phase was washed (water), dried (magnesium sulphate) and evaporated to give ethyl 3-(2-chloroethoxy)- 4-fluoro-2-methylthiobenzoate (59.9g), NMR 1.4(t,3H), 2.5(s,3H), 3.8(m,2H), 4.3-4.4(m,4H), 7.0(m,1H), 7.3(m,1H).

Reference Example 11 By proceeding according to the method in Example 4 there was prepared from methyl 2-fluoro-4-trifluoromethylbenzoate, 2-(1,2,4- triazol-l-yl)-4-trifluoromethylbenzoic acid, NMR 3.8(s,3H), 7.8(m,2H), 8.1(m,2H), 8.4(s,1H).

Reference Example 12 To a suspension of 4-(1,2,4-triazol-1-yl)-2-trifluoromethylbenzoic acid (2.57g) and a catalytic amount of N,N-dimethylformamide in dichloromethane was added oxalyl chloride (2.2ml) dropwise at 200C.

The mixture was stirred for 3 hours and evaporated. To a suspension of the residue in acetone was added 1,3-dimethyl-5-hydroxy-lH-pyrazole (1.23g) and potassium carbonate (0.76g) dropwise at 200C. The mixture was stirred for 0.5 hour and water and dichloromethane added. The organic layer was dried (magnesium sulfate), evaporated and the residue purified by chromatography to give 1,3-dimethyl-5-[4-(1,2,4-triazol-1- yl)-2-trifluoromethylbenzoyloxy] - 1 H-pyrazole (1.93 g), NMR 2.27(s,3H), 3.71(s,3H), 6.12(s,lH), 8.05-8.28(4H), 8.76(s,lH).

By proceeding in a similar manner the following compounds were also prepared:

1 -methyl-5-[4-(1,2,4-triazol- 1 -yl)-2-trifluoromethylbenzoyloxy]- 1H-pyrazole, NMR 3.8(s,3H), 6.33(1H), 7.48(1H), 8.08(d,1H), 8.2(d,lH), 8.21(s,1H), 8.76(s,1H); and 1,3 -dimethyl-5-[4-( 1 ,2,4-triazol- 1 -yl)-2-chlorobenzoyloxy]- 1 H- pyrazole, NMR 2.28 (s, 3H), 3.75 (s, 3H), 7.77 (d, 1H), 7.99 (s, 1H), 8.16-8.25 (m, 2H), 8.69 (s, 1H).

Reference Example 13 To a solution of methyl 4-fluoro-2-trifluoromethylbenzoate (4.95g) in N,N-dimethylformamide was added 1,2,4-triazole (2.0g) and potassium carbonate (4.0g) at 200C and the mixture stirred for 4 hours at 600C. The mixture was diluted (ether), washed (aqueous citric acid) and dried (magnesium sulfate). The residue was purified by chromatography to give methyl 4-(1,2,4-triazol-1-yl)-2- trifluoromethylbenzoate (5.07g), NMR 3.98(s,3H),7.94- 8.05(2H),8.15(2H),8.71(s,lH).

By proceeding in a similar manner the following compound was also prepared: methyl 2-chloro4-(1,2,4-triazol-1 -yl)benzoate, NMR 3.97 (s, 3H), 7.68 (d, 1H), 7.89 (s, 1H), 8.02 (s, 1H), 8.14 (s, 1H), 8.70 (s, 1H).

Reference Example 14 To a solution of methyl 4-(1,2,4-triazol-1-yl)-2- trifluoromethylbenzoate (5.07g) in methanol was added aqueous sodium hydroxide (1.50g) at 200C. The mixture was stirred for 4 hours, partially evaporated and extracted with ether. The aqueous layer was acidified (aqueous citric acid) and extracted with ethyl acetate. The organic layer was dried (magnesium sulfate), and evaporated to give 4-(1,2,4-triazol- l-yl)-2-trifluoromethylbenzoic acid (3.32g), NMR 8.25(1H), 8.34- 8.42(3H), 1 0.00(s,1H).

By proceeding in a similar manner the following compound was also prepared: 2-chloro4-(1,2,4-triazol-1-yl)benzoic acid, NMR 7.71 (d, 1H), 7.93 (s, 1H), 8.05-8.18 (m, 1H), 8.82 (s, 1H).

According to a further feature of the present invention, there is provided a method for controlling the growth of weeds (i.e. undesired vegetation) at a locus which comprises applying to the locus a

herbicidally effective amount of at least one phenyl derivative of formula (I) or an agriculturally acceptable salt or metal complex thereof.

For this purpose, the phenyl derivatives are normally used in the form of herbicidal compositions (i.e. in association with compatible diluents or carriers and/or surface active agents suitable for use in herbicidal compositions), for example as hereinafter described.

The compounds of formula (I) show herbicidal activity against dicotyledonous (i.e. broad-leafed) and monocotyledonous (i.e. grass) weeds by pre- and/or post-emergence application.

By the term "pre-emergence application" is meant application to the soil in which the weed seeds or seedlings are present before emergence of the weeds above the surface of the soil. By the term "post- emergence application" is meant application to the aerial or exposed portions of the weeds which have emerged above the surface of the soil.

For example, the compounds of formula (I) may be used to control the growth of: broad-leafed weeds, for example, Abutilon theophrasti, Amaranthus retroflexus, Bidens tilosa, Chenopodium album, Galium aparine, Ipomoea sDD. e.g. Ipomoea purpurea, Sesbania exaltata, Sinapis arvensis, Solanum nigrum and Xanthium strumarium, and grass weeds, for example Alopecurus myosuroides, Avena fatua, Digitaria sanguinalis, Echinochloa crus-galli, Sorghum bicolor, Eleusine indica and Setaria spp, e.g. Setaria faberii or Setaria viridis, and sedges, for example, Cyperus esculentus.

The amounts of compounds of formula (I) applied vary with the nature of the weeds, the compositions used, the time of application, the climatic and edaphic conditions and (when used to control the growth of weeds in crop-growing areas) the nature of the crops. When applied to a crop-growing area, the rate of application should be sufficient to control the growth of weeds without causing substantial permanent damage to the crop. In general, taking these factors into account, application rates from 0.01kg to 2kg of active material per hectare give good results.

However, it is to be understood that higher or lower application rates may be used, depending upon the particular problem of weed control encountered.

The compounds of formula (I) may be used to control selectively the growth of weeds, for example to control the growth of those species hereinbefore mentioned, by pre- or post-emergence application in a directional or non-directional fashion, e.g. by directional or non- directional spraying, to a locus of weed infestation which is an area used, or to be used, for growing crops, for example cereals, e.g. wheat, barley, oats, maize and rice, soya beans, field and dwarf beans, peas, lucerne, cotton, peanuts, flax, onions, carrots, cabbage, oilseed rape, sunflower, sugar beet, and permanent or sown grassland before or after sowing of the crop or before or after emergence of the crop. For the selective control of weeds at a locus of weed infestation which is an area used, or to be used, for growing of crops, e.g. the crops hereinbefore mentioned, application rates from 0:01kg to 1.0kg, and preferably from 0.025kg to 0.25kg, of active material per hectare are particularly suitable.

The compounds of formula (I) may also be used to control the growth of weeds, especially those indicated above, by pre- or post- emergence application in established orchards and other tree-growing areas, for example forests, woods and parks, and plantations, e.g. sugar cane, oil palm and rubber plantations. For this purpose they may be applied in a directional or non- directional fashion (e.g. by directional or non-directional spraying) to the weeds or to the soil in which they are expected to appear, before or after planting of the trees or plantations at application rates from 0.25kg to 2.0kg, and preferably from 0.25kg to 1.0kg of active material per hectare.

The compounds of formula (I) may also be used to control the growth of weeds, especially those indicated above, at loci which are not crop-growing areas but in which the control of weeds is nevertheless desirable.

Examples of such non-crop-growing areas include airfields, industrial sites, railways, roadside verges, the verges of rivers, irrigation and other waterways, scrublands and fallow or uncultivated land, in particular where it is desired to control the growth of weeds in order to reduce fire risks. When used for such purposes in which a total herbicidal effect is frequently desired, the active compounds are normally applied at dosage rates higher than those used in crop-growing

areas as hereinbefore described. The precise dosage will depend upon the nature of the vegetation treated and the effect sought.

Pre- or post-emergence application, and preferably pre-emergence application, in a directional or non-directional fashion (e.g. by directional or non-directional spraying) at application rates from 0.5kg to 2.0kg, and preferably from 0.5kg to 1.0kg, of active material per hectare are particularly suitable for this purpose.

When used to control the growth of weeds by pre-emergence application, the compounds of formula (I) may be incorporated into the soil in which the weeds are expected to emerge. It will be appreciated that when the compounds of formula (I) are used to control the growth of weeds by post-emergence application, i.e. by application to the aerial or exposed portions of emerged weeds, the compounds of formula (I) will also normally come into contact with the soil and may also then exercise a pre-emergence control on later-germinating weeds in the soil.

Where especially prolonged weed control is required, the application of the compounds of formula (I) may be repeated if required.

According to a further feature of the present invention, there are provided compositions suitable for herbicidal use comprising one or more of the phenyl derivatives of formula (I) or an agriculturally acceptable salt or metal complex thereof; in association with, and preferably homogeneously dispersed in, one or more compatible agriculturally- acceptable diluents or carriers and/or surface active agents [i.e. diluents or carriers and/or surface active agents of the type generally accepted in the art as being suitable for use in herbicidal compositions and which are compatible with compounds of formula (I)].

The term "homogeneously dispersed" is used to include compositions in which the compounds of formula (I) are dissolved in other components.

The term "herbicidal compositions" is used in a broad sense to include not only compositions which are ready for use as herbicides but also concentrates which must be diluted before use. Preferably, the compositions contain from 0.05 to 90% by weight of one or more compounds of formula (I).

The herbicidal compositions may contain both a diluent or carrier and surface-active (e.g. wetting, dispersing, or emulsifying) agent.

Surface-active agents which may be present in herbicidal compositions

of the present invention may be of the ionic or non-ionic types, for example sulphoricinoleates, quaternary ammonium derivatives, products based on condensates of ethylene oxide with alkyl and polyaryl phenols, e.g. nonyl- or octyl-phenols, or carboxylic acid esters of anhydrosorbitols which have been rendered soluble by etherification of the free hydroxy groups by condensation with ethylene oxide, alkali and alkaline earth metal salts of sulphuric acid esters and sulphonic acids such as dinonyl- and dioctyl-sodium suiphonosuccinates and alkali and alkaline earth metal salts of high molecular weight sulphonic acid derivatives such as sodium and calcium lignosulphonates and sodium and calcium alkylbenzene sulphonates.

Suitably, the herbicidal compositions according to the present invention may comprise up to 10% by weight, e.g. from 0.05% to 10% by weight, of surface-active agent but, if desired, herbicidal compositions according to the present invention may comprise higher proportions of surface-active agent, for example up to 15% by weight in liquid emulsifiable suspension concentrates and up to 25% by weight in liquid water soluble concentrates.

Examples of suitable solid diluents or carriers are aluminium silicate, talc, calcined magnesia, kieselguhr, tricalcium phosphate, powdered cork, absorbent carbon black and clays such as kaolin and bentonite. The solid compositions (which may take the form of dusts, granules or wettable powders) are preferably prepared by grinding the compounds of formula (I) with solid diluents or by impregnating the solid diluents or carriers with solutions of the compounds of formula (I) in volatile solvents, evaporating the solvents and, if necessary, grinding the products so as to obtain powders. Granular formulations may be prepared by absorbing the compounds of formula (I) (dissolved in suitable solvents, which may, if desired, be volatile) onto the solid diluents or carriers in granular form and, if desired, evaporating the solvents, or by granulating compositions in powder form obtained as described above. Solid herbicidal compositions, particularly wettable powders and granules, may contain wetting or dispersing agents (for example of the types described above), which may also, when solid, serve as diluents or carriers.

Liquid compositions according to the invention may take the form of aqueous, organic or aqueous-organic solutions, suspensions and emulsions which may incorporate a surface-active agent. Suitable liquid diluents for incorporation in the liquid compositions include water, glycols, tetrahydrofurfuryl alcohol, acetophenone, cyclohexanone, isophorone, toluene, xylene, mineral, animal and vegetable oils and light aromatic and naphthenic fractions of petroleum (and mixtures of these diluents). Surface-active agents, which may be present in the liquid compositions, may be ionic or non-ionic (for example of the types described above) and may, when liquid, also serve as diluents or carriers.

Powders, dispersible granules and liquid compositions in the form of concentrates may be diluted with water or other suitable diluents, for example mineral or vegetable oils, particularly in the case of liquid concentrates in which the diluent or carrier is an oil, to give compositions ready for use.

Liquid concentrates in which the diluent or carrier is an oil may be used without further dilution using the electrostatic spray technique.

Herbicidal compositions according to the present invention may also contain, if desired, conventional adjuvants such as adhesives, protective colloids, thickeners, penetrating agents, spreading agents, stabilisers, sequestering agents, anti-caking agents, colouring agents and corrosion inhibitors. These adjuvants may also serve as carriers or diluents.

Herbicidal compositions according to the present invention may also comprise the compounds of formula (I) in association with, and preferably homogeneously dispersed in, one or more other pesticidally active compounds and, if desired, one or more compatible pesticidally acceptable diluents or carriers, surface-active agents and conventional adjuvants as hereinbefore described.

Examples of other pesticidally active compounds which may be included in, or used in conjunction with, the herbicidal compositions of the present invention include herbicides, for example to increase the range of weed species controlled for example alachlor [2-chloro-2,6'- diethyl-N-(methoxy-methyl)-acetanilide], atrazine [2-chloro-4- ethylamino-6-isopropylamino-1,3,5-triazine], bromoxynil [3,5-dibromo-

4-hydroxybenzonitrile], chlortoluron [N'-(3 -chloro-4-methylphenyl)- N,N-dimethylurea], cyanazine [2-chioro-4-(l -cyano-l- methylethylamino)-6-ethylamino- 1,3 ,5-triazine], 2,4-D [2,4- dichlorophenoxy-acetic acid], dicamba [3,6-dichloro-2-methoxybenzoic acid], difenzoquat [1,2- dimethyl-3,5-diphenyl-pyrazolium salts], flampropmethyl [methyl N-2-(N- benzoyl-3-chloro-4-fluoroanilino)- propionate], fluometuron [N'-(3-trifluoro- methylphenyl)-N,N- dimethylurea], isoproturon [N'-(4-isopropylphenyl)-N,N-dimethylurea], insecticides, e.g. synthetic pyrethroids, e.g permethrin and cypermethrin, and fungicides, e.g. carbamates, e.g. methyl N-(1-butyl-carbamoyl- benzimidazol-2-yl)carbamate, and triazoles e.g. 1 -(4-chloro-phenoxy)- 3,3 -dimethyl- 1 -(1 ,2,4-triazol- 1 -yl)-butan-2-one.

Pesticidally active compounds and other biologically active materials which may be included in, or used in conjunction with, the herbicidal compositions of the present invention, for example those hereinbefore mentioned, and which are acids, may, if desired, be utilised in the form of conventional derivatives, for example alkali metal and amine salts and esters.

The following Examples illustrate herbicidal compositions according to the present invention. The following trade marks appear in the Examples: Synperonic, Solvesso, Arylan, Arkopon, Sopropon, Tixosil, Soprophor, Attagel, Rhodorsil.

Example C1: An emulsifiable concentrate is formed from: Active ingredient (Compound 1) 20% w/v N-Methylpyrrolidinone (NMP) 25% w/v Calcium dodecylbenzenesulphonate 70% (CaDDBS) (Arylan CA) 4% w/v Nonylphenol ethylene oxide propylene oxide condensate (NPEOPO) (Synperonic NPE 1800) 6% w/v Aromatic solvent (Solvesso) to 100 volumes by stirring NMP, active ingredient (Compound 1), CaDDBS, NPEOPO and Aromatic solvent until a clear solution is formed, and adjusting to volume with Aromatic solvent.

Example C2 A wettable powder is formed from: Active ingredient (Compound 1) 50% w/w Sodium dodecylbenzenesulphonate (Arylan SX85) 3% w/w Sodium methyl oleoyl taurate (Arkopon T) 5% w/w Sodium polycarboxylate (Sopropon T36) 1% w/w Microfine silicon dioxide (Tixosil 38) 3% w/w China clay 38% w/w by blending the above ingredients together and grinding the mixture in an air jet mill.

Example C3 A suspension concentrate is formed from: Active ingredient (Compound 1) 50% w/v Antifreeze (Propylene glycol) 5% w/v Ethoxylated tristyrylphenol phosphate (Soprophor FL) 0.5% w/v Nonyl phenol 9 mole ethoxylate (Ethylan BCP) 0.5% w/v Sodium polycarboxylate (Sopropon T36) 0.2% w/v Attaclay (Attagel) 1.5% w/v Antifoam (Rhodorsil AF426R) 0.003% w/v Water to 100 volumes by stirring the above ingredients together and milling in a bead mill.

Example C4 A water dispersible granule is formed from: Active ingredient (Compound 1) 50% w/w Sodium dodecylbenzenesulphonate (Arylan SX 85) 3% w/w Sodium methyl oleoyl taurate (Arkopon T) 5% w/w Sodium polycarboxylate (Sopropon T36) 1% w/w Binder (Sodium lignosulphonate) 8% w/w

China clay 30% w/w Microfine silicon dioxide (Tixosil 38) 3% w/w by blending the above ingredients together, grinding the mixture in an air jet mill and granulating by addition of water in a suitable granulation plant (e.g. Fluid bed drier) and drying. Optionally the active ingredient may be ground either on its own or admixed with some or all of the other ingredients.

The compounds of the invention have been used in herbicidal applications according to the following procedures.

METHOD OF USE OF HERBICIDAL COMPOUNDS: TEST METHOD A a) General Appropriate quantities of the compounds used to treat the plants were dissolved in acetone to give solutions equivalent to application rates of up to 1000g test compound per hectare (g/ha). These solutions were applied from a standard laboratory herbicide sprayer delivering the equivalent of 290 litres of spray fluid per hectare. The weed species used in the test were as follows:- Broadleaf weeds: Abutilon theophrasti, Amaranthus retroflexus, Galium aparine, Inomoea Duwurea, Xanthium strumarium; Grassweeds: Alorecums mvosuroides, Avena fatua, Echinochloa crus-nalli, Setaria viridis; Sedges: Cvperus esculentus.

The crop species used in the test were as follows:- Cotton, Soya, Maize, Rice and Wheat. b) Weed control : Pre-emergence The seeds were sown in 70 mm square, 75 mm deep plastic pots in non-sterile soil

The compounds of the invention were applied to the soil surface, containing the seeds, as described in (a). A single pot of each crop and each weed was allocated to each treatment, with unsprayed controls and controls sprayed with acetone alone.

After treatment the pots were placed on capillary matting kept in a glass house, and watered overhead . Visual assessment of crop damage was made 20-24 days after spraying. The results were expressed as the percentage reduction in growth or damage to the crop or weeds, in comparison with the plants in the control pots. c) Weed control : Post-emergence The weeds and crops were sown directly into John Innes potting compost in 75 mm deep, 70 mm square pots except for Amaranthus which was pricked out at the seedling stage and transferred to the pots one week before spraying. The plants were then grown in the greenhouse until ready for spraying with the compounds used to treat the plants.

The compounds used to treat the plants were applied to the plants as described in (a). A single pot of each crop and weed species was allocated to each treatment, with unsprayed controls and controls sprayed with acetone alone.

After treatment the pots were placed on capillary matting in a glass house, and watered overhead once after 24 hours and then by controlled sub-irrigation. Visual assessment of crop damage and weed control was made 20-24 days after spraying. The results were expressed as the percentage reduction in growth or damage to the crop or weeds, in comparison with the plants in the control pots.

TEST METHOD B Paddy post-emergence application in greenhouse Paddy field soil was filled in 170 cm2 plastic pots, a suitable amount of water and chemical fertilisers were added thereto and kneaded to convert it to a state of a paddy.

Paddy rice plants (variety; Koshihikari), that had been grown in advance in a greenhouse to a stage of two leaves, were transplanted to each pot (two seedlings per pot). Then in each pot there were sown predetermined amounts of seeds of Echinochloa orvzicola, Monochoria

vaginalis, Lindernia procumbens and Scirnus iuncoides respectively, and water was added to a depth of 3 cm.

After having grown the plants in a greenhouse until Echinochloa orvzicola reached a stage of 1.5 leaves, solutions were prepared in 100% acetone using compounds described in the Examples so that they contained active ingredients in an amount equivalent to 75, 300 and 1200 g/ha. The solutions were applied by dropping with a pipette.

After 21 days from the application with the chemicals, herbicidal effects on each weed and phytotoxicity on paddy rice plants were visually assessed, and the results expressed as the percentage reduction in growth or damage to the crop or weeds in comparison with the plants in the control pots.

When applied pre- or post-emergence in Test Method A at 1000g/ha or less compounds 1, 4-6, 8, 12, 15-17, 19-29, 39, 502, 517, 546 and 1116-1128 of the invention gave at least 80% reduction in growth of one or more of the weed species; at levels of application toxic to the weeds these compounds were selective in at least one of the crop species.

When applied at 1200 g/ha or less, in Test Method B, compounds 1-15, 18-27,49, 501-507, 509-517, 546 and 1116-1132 ofthe invention gave at least 90% reduction in growth of one or more of the weed species listed above.