Abstract:
Fungicidal pyrimidine derivatives and the use as a fungicide of the compounds of formula (1):                            
     wherein R 1  is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 3 -C 6 cycloalkoxy, C 1 -C 6 alylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, phenyl, pyridinyl or azolyl groups, (being optionally substituted by one or more substituents); or N(R 4 )C(O)R 5 , R 2  is polyfluoroalkyl, R 3  is fluorine, chlorine, bromine or iodine; ethenyl or ethynyl (being optionally substituted by one or more of halogen), R 4  and R 5  are, independently, H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl groups, (being optionally substituted by one or more of halogen or cyano); or R 4  and R 5  can join together to form a 5 or 6-membered ring, Q is a heteroaromatic ring selected from the following ring system; imidazol-1-yl, pyrazol-1-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, 1,2,4-triazol-1-yl, 1,2,4-triazol-1-yl, benzimidazol-1-yl or tetrazol-5-yl groups, (being optionally substituted by one or more of substituents).

Description:
BACKGROUND OF THE INVENTION 
     1. Field of the Invention 
     The present invention relates to novel pyrimidine derivatives, which have fungicidal activity. The preparation and use, in agriculture and horticulture, of agrochemical compositions containing these novel fungicidal pyrimidines are also disclosed. 
     2. Description of the Related Art 
     It is known in the art that certain pyrimidine derivatives such as those disclosed in PCT application WO 2003-000659 have fungicidal and insecticidal properties, WO 2002-067694 have pesticidal properties, EP 337943 have herbicidal and plant growth regulatory properties, U.S. Pat. No. 4,474,599 have herbicidal properties and in the art that PCT application WO 94-08975 have herbicidal and fungicidal properties. In the arts that WO 2002-047690, WO 99-02503, WO 96-33972 and U.S. Pat. No. 3,149,109 also have description about heteroaromatic substituted pyrimidine derivatives. 
     SUMMARY OF THE INVENTION 
     In accordance with the present invention, pyrimidine derivatives are provided having the formula (1):                           
     Wherein 
     R 1  is H, C 1 -C 6 alkyl (being optionally substituted by one or more of halogen), C 2 -C 6 alkenyl (being optionally substituted by one or more of halogen), C 2 -C 6 alkynyl (being optionally substituted by one or more of halogen or trialkylsilyl), C 1 -C 6 alkoxy (being optionally substituted by one or more of halogen), C 2 -C 6 alkenyloxy (being optionally substituted by one or more of halogen), C 2 -C 6 alkynyloxy (being optionally substituted by one or more of halogen), C 1 -C 6 alkylthio (being optionally substituted by one or more of halogen), C 1 -C 6 alkylsulfinyl (being optionally substituted by one or more of halogen), C 1 -C 6 alkylsulfonyl (being optionally substituted by one or more of halogen), phenyl (being optionally substituted by one or more of halogen, alkyl, haloalkyl or alkoxy), pyridin-2-yl (being optionally substituted by one or more of halogen, alkyl, haloalkyl or phenyl), pyridin-3-yl (being optionally substituted by one or more of halogen, alkyl, haloalkyl or phenyl), pyridinyl (being optionally substituted by one or more of halogen, alkyl, haloalkyl or phenyl), imidazol-1-yl (being optionally substituted by one or more of halogen, alkyl or alkoxyl pyrazol-1-yl (being optionally substituted by one or more of halogen, alkyl or alkoxy) or N(R 4 )C(O)R 5 , 
     R 2  is haloC 1 -C 6 alkyl, 
     R 3  is halogen, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl groups, (being optionally substituted by one or more of halogen), 
     R 4  and R 5  are, independently, H, C 1 -C 6 alkyl (being optionally substituted by one or more of halogen or cyano); or R 4  and R 5  can join together to form a 5 or 6-membered ring, 
     Q is a heteroaromatic ring selected from the following ring system; imidazol-1-yl, pyrazol-1-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, 1,2,4-triazol-1-yl, 1,2,4-triazol-4-yl, benzimidazol-1-yl or tetrazol-5-yl groups (being optionally substituted by one or more of halogen, cyano, hydroxy, mercapto, alkyl, haloalkyl, alkoxy, alkoxycarbonyl, amino, alkylamino, haloalkoxy, alkylthio or aralkylthio). 
     The present invention is directed to agrochemical compositions comprising as an active ingredient at least one of the novel pyrimidine derivatives of the present invention, as well as to the use of these active ingredients or compositions for plant disease control and in particular as fungicides useful in agriculture and horticulture. 
     For a better understanding of the present invention, reference is made to the following description and its scope will be pointed out in the appended claims. 
    
    
     DETAILED DESCRIPTION OF THE INVENTION 
     For purposes of the present invention the general terms used hereinabove and hereinbelow have the following meanings, unless otherwise defined: 
     Alkyl groups are, in accordance with the number of carbon atoms, straight-chain or branched and will typically be methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-amyl, tert-amyl, 1-hexyl or 3-hexyl. 
     Halogen and halo substituents will be understood generally as meaning fluoro, chloro, bromo, iodo, 
     Haloalkyl can contain identical or different halogenatoms, typically fluoromethyl, difluoromethyl, difluorochloromethyl, trifluoromethyl, chloromethyl, trichloromethyl. 
     Alkoxy is typically methoxy, ethoxy, propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, sec-butyloxy and tert-butyloxy. 
     Alkenyl and alkynyl groups preferably contain from 2 to 6, more preferably from 2 to 4, carbon atoms. They can be in the form of straight or branched chains, and, where appropriate, the alkenyl groups can be of either (E) or (Z)-configuration. Examples are vinyl, ethynyl, propynyl. 
     The present invention provides the use as fungicides of pyrimidine derivatives having the following formula (1):                           
     Wherein R 1  is H, C 1 -C 6 alkyl (being optionally substituted by one or more of halogen), C 2 -C 6 alkenyl (being optionally substituted by one or more of halogen), C 2 -C 6 alkynyl (being optionally substituted by one or more of halogen or trialkylsilyl), C 1 -C 6 alkoxy (being optionally substituted by one or more of halogen), C 2 -C 6 alkenyloxy (being optionally substituted by one or more of halogen), C 2 -C 6 alkynyloxy (being optionally substituted by one or more of halogen), C 1 -C 6 alkylthio (being optionally substituted by one or more of halogen), C 1 -C 6 alkylsulfinyl (being optionally substituted by one or more of halogen), C 1 -C 6 alkylsulfonyl (being optionally substituted by one or more of halogen), phenyl (being optionally substituted by one or more of halogen, alkyl, haloalkyl or alkoxy), pyridin-2-yl (being optionally substituted by one or more of halogen, alkyl, haloalkyl or phenyl), pyridin-3-yl (being optionally substituted by one or more of halogen, alkyl, haloalkyl or phenyl), pyridin-4-yl (being optionally substituted by one or more of halogen, alkyl, haloalkyl or phenyl), imidazol-1-yl (being optionally substituted by one or more of halogen, alkyl or alkoxy), pyrazol-1-yl (being optionally substituted by one or more of halogen, alkyl or alkoxy) or N(R 4 )C(O)R 5 , 
     R 2  is haloC 1 -C 6 akyl, R 3  is halogen, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl groups, (being optionally substituted by one or more of halogen), R 4  and R 5  are, independently, H, C 1 -C 6 alkyl (being optionally substituted by one or more of halogen or cyano); or R 4  and R 3  can join together to form a 5 or 6membered ring, 
     Q is a heteroaomatic ring selected from the following ring system; imidazol-1-yl, pyrazol-1-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, 1,2,4-triazol-1-yl, 1,2,4-triazol-4-yl, benzimidazol-1-yl or tetrazol-5-yl groups (being optionally substituted by one or more of halogen, cyano, hydroxy, mercapto, alkyl, haloalkyl, alkoxy, alkoxycarbonyl, amino, alkylamino, haloalkoxy, alkylthio or aralkylthio). 
     Examples of specific compounds of formula (1) which are of use as fungicides include the compounds listed in Table 1. 
     The pyrimidine derivative represented by the formula (1) in the invention can be prepared by the following process.                           
     The preparation of 5-halogenated 4chloropyrimidines (wherein R 1 =H, alkyl phenyl, pyridine-2-yl, pyridine-3-yl or pyridine-4-yl) such as 14 as intermediates that can be used for the synthesis of compounds within the scope of the present invention is detailed in Scheme 1. Pyrimidinones of structure 1-2 can be synthesized by condensation of a β-keto-ester with amidine (or amidine salt) in a suitable solvent such as methanol, ethanol, isopropanol or the like in the presence of a base such as sodium or potassium alkoxide. The pyrimidinones 1-2 thus obtained can be halogenated by treatment with a suitable halogenating agent such as bromine, chlorine, iodine monochloride, N-bromosuccinimide, N-chlorosuccinimide or N-iodosuccinimide in a suitable solvent such as dichloromethane, chloroform, carbon tetrachloride, acetonitrile or N,N-dimethylformamide to give a halogenated pyrimidinone at 5-position of structure 1-3 (wherein R 3 =Cl, Br, I). The pyrimidinone can be chlorinated by treatment with phosphoryl chloride, phosphorous pentachloride, phosphorous trichloride or mixtures thereof or with chloromethylenedimethylammonium chloride added separately of prepared in situ by treatment of N,N-dimethylformamide with thionyl chloride, phosgene or the like in dichloromethane, chloroform, tetrahydrofuran, dioxane, ether or other suitable solvent to give a 4-chloropyrimidine of structure 1-4.                           
     The 4-chloropyrimidines (wherein R=alkyl) such as 2-5 as intermediates, that can be used for the synthesis of compounds within the scope of the present invention, can be prepared according to  Journal of Heterocyclic Chemistry, Vol . 20, 219 (1983). The method for the preparation is detailed in Scheme 2.                           
     The preparation of 2-alkylsulfonyl-4-chloropyrimidines such as 3-2 as intermediates that can be used for the synthesis of compounds within the scope of the present invention is detailed in Scheme 3. A 2-alkylthio-4-chloropyrimidine 3-1 is treated with oxidizing agent such as hydrogen peroxide or m-chloroperbenzoic acid in a suitable solvent such as dichloromethane, chloroform, acetic acid or the like to give a 2-alkylsulfonyl-4-chloropyrimidine of structure 3-2.                           
     The preparation of 2-alkoxy-4-chloropyrimidines such as 4-2 as intermediates that can be used for the synthesis of compounds within the scope of the present invention is detailed in Scheme 4. A 2-alkylsulfonyl-4-chloropyrimidine 4-1 is treated with an alcohol in the presence of a base such as sodium hydride, sodium bis(trimethylsilyl)amide, potassium tert-butoxide or the like to give a 2-alkoxy-4-chloropyrimidine of structure 4-2.                           
     The preparation of 2-alkylcarbonylamino-4-chloropyrimidines such as 5-3 as intermediates that can be used for the synthesis of compounds within the scope of the present invention is detailed in Scheme 5. A 2-alkysulfonyl-4-chloropyrimidine 5-1 is treated with a carboxylic amide 5-2 in the presence of a base such as sodium hydride, sodium bis(trimethylsilyl)amide, potassium tert-butoxide or the like to give a 2-alkoxy-4-chloropyrimidine of structure 5-3.                           
     The preparation of 5-halogeno-4-methoxypyrimidines such as 6-2 as intermediates that can be used for the synthesis of compounds within the scope of the present invention is detailed in Scheme 6. A 4-chloropyrimidine of structure 6-1 is treated with sodium methoxide in a suitable solvent such as methanol, tetrahydrofuran or the like to give a 4methoxypyrimidine of structure 6-2.                           
     The preparation of 5-alkenylpyrimidinones such as 7-4 as intermediates that can be used for the synthesis of compounds within the scope of the present invention is detailed in Scheme 7. A 5-halogenooxypyrimidine 7-1 (halogen=Br or I) is treated with alkenyltributyltin 7-2 in the presence of a catalyst such as tetrakis(triphenylphosphine)palladium(0), dichlorobis(triphenylphosphine)palladium(II), triphenylarsinepalladium(0) or the like in a suitable solvent such as N,N-dimethylformamide, acetonitrlile, dioxane, tetrahydrofuran, toluene or other suitable solvent to give a 5-alkeny-4-methoxypyrimidine of structure 7-3. The 5-alkenyl-4-methoxypyrimidine thus obtained is treated with 6N-HCl under reflux to give a 5-alkenylpyrimidinone of structure 7-4.                           
     The preparation of 5-alkynyl-4-methoxypyrimidines such as 8-3 as intermediates that can be used for the synthesis of compounds within the scope of the present invention is detailed in Scheme 8. A 5-halogeno-4-methoxypyrimidine 8-1 (halogen=Br or I) is treated with alkyne 8-2 in the presence of amine such as triethylamine, n-propylamine, N,N-diisopropylethylamine or the like, copper(I) iodide and catalyst such as tetrakis(triphenylphosphine)palladium(0), dichlorobis(triphenylphosphine)palladium(II) or the like in a suitable solvent such as N,N-dimethylformamide, acetonitrlile, dioxane, tetrahydrofuran, toluene or other suitable solvent to give a 5-alkynyl-4-methoxypyrimidine of structure 8-3.                           
     The preparation of 5-fluoro-4-methoxypyrimidines such as 9-2 as intermediates that can be used for the synthesis of compounds within the scope of the present invention is detailed in Scheme 9. A 5-halogeno-4-methoxypyrimidine 9-1 (halogen=Br or I) is treated with n-butyl lithium under dry ice cooling, then with fluorinating agent such as N-fluorobenzenesulfonimide, 1-fluoropyridinium tetrafluoroborate or the like in a suitable solvent such as tetrahydrofurwan, ether or other suitable solvent to give a 5-fluoro-4-methoxypyrimidine of structure 9-2.                           
     The preparation of some 4-azolylpyrimidines such as 10-3 within the scope of the present invention is detailed in Scheme 10. An azole 10-1 is condensed with a 4-chloropyrimidine 10-2 in a suitable solvent such as dimethysulfoxide, acetonitrile, tetrahydrofuran, toluene, isopropanol or the like in the presence or absence of a base such as sodium hydride, sodium hydroxide, potassium carbonate, 1,8-diazabicyclo-([5,4,0]-undec-7-ene, N,N-diisopropylethylamine or the like at or above room temperature to give a 4-azolylpyrimidine of structure 10-3.                           
     The preparation of some 4-tetrazolyl pyrimidines such as 11-3, 11-4 and 11-5 within the scope of the present invention is detailed in Scheme 11. A 4-chloropyrimidine 11-1 is treated with cyanating agent such as sodium or potassium cyanide in a suitable solvent such as water, isopropanol, acetonitrile, propionitrile, tetrahydrofuran, N,N-dimethylformamide, dimethylsulfoxide or mixture thereof, or other suitable solvent to give a 4-cyanopyrimidine of structure 11-2. The 4-chloropyrimidine 11-1 can first be activated by addition of 4-(dimethylamino)pyridine prior to be added cyanating agent. The 4-cyanopyrimidine thus obtained is treated with sodium azide in a suitable solvent such as water, isopropanol, acetonitrile, propionitrile, tetrahydrofuran, N,N-dimethylformamide, dimethylsulfoxide or mixture thereof or other suitable solvent to give 4-tetrazolylpyrimidine of structure 11-3. This reaction can be accelerated by adding zinc bromide or other zinc halides. The 4-tetrazolylpyrimidine thus obtained can be methylated by treatment with trimethylsilyldiazomethane or alkylated by treatment with a suitable alkylating agent such as dimethyl sulfate, diethyl sulfate, methyl iodide, isopropyl iodide or the like in the presence or absence of an inorganic base such as sodium hydroxide, potassium hydroxide, sodium hydride and potassium carbonate or organic base such as triethylamine and pyridine to give a alkylated tetrazolylpyrimidine of structure 11-4 or 11-5. 
     The compounds of the present invention can show excellent fungicidal activity against wide varieties of fungi, and therefore, the compounds can be useful for plant disease control in the farming of agricultural and horticultural crops including ornamental flowers, turf and forage crops. 
     The examples for the plant diseases might to be controlled with the compounds of the present invention are given in the following. 
     
       
         
               
               
             
           
               
                   
               
             
             
               
                 Paddy rice 
                   
               
               
                 Blast 
                 ( Pyricularia oryzae ) 
               
               
                 Sheath blight 
                 ( Rhizoctonia solani ) 
               
               
                 Bakanae disease 
                 ( Gibberella fujikuroi ) 
               
               
                 Helminthosporium leaf spot 
                 ( Cochliobolus miyabeanus ) 
               
               
                 Barley 
               
               
                 Loose smut 
                 ( Ustilago muda ) 
               
               
                 Wheat 
               
               
                 Scab 
                 ( Gibberella zeae ) 
               
               
                 Leaf rust 
                 ( Puccinia recondita ) 
               
               
                 Eye spot 
                 ( Pseudocercosporella herpotrichoides ) 
               
               
                 Glume blotch 
                 ( Leptosphaeria nodorum ) 
               
               
                 Powdery mildew 
                 ( Erysiphe graminis f sp. tritici ) 
               
               
                 Fusarium snow blight 
                 ( Micronectriella nivalis ) 
               
               
                 Potato 
               
               
                 Late blight 
                 ( Phytophthora infestans ) 
               
               
                 Gray mold 
                 ( Botrytis cinerea ) 
               
               
                 Ground nut 
               
               
                 Leaf spot 
                 ( Mycosphaerella aradius ) 
               
               
                 Sugar beat 
               
               
                 Cercospora leaf spot 
                 ( Cercospora beticola ) 
               
               
                 Soybean 
               
               
                 Gray mold 
                 ( Botrytis cinerea ) 
               
               
                 Kidney beans 
               
               
                 Gray mold 
                 ( Botrytis cinerea ) 
               
               
                 Cucumber 
               
               
                 Powdery mildew 
                 ( Sphaerotheca fuliginea ) 
               
               
                 Sclerotinia rot 
                 ( Sclerotinia sclerotiorum ) 
               
               
                 Gray mold 
                 ( Botrytis cinerea ) 
               
               
                 Downy mildew 
                 ( Pseudoperonospora cubensis ) 
               
               
                 Tomato 
               
               
                 Leaf mold 
                 ( Cladosporium fulvum ) 
               
               
                 Late blight 
                 ( Phytophthora infestans ) 
               
               
                 Gray mold 
                 ( Botrytis cinerea ) 
               
               
                 Egg plant 
               
               
                 Black rot 
                 ( Corynespora melongenae ) 
               
               
                 Onion 
               
               
                 Gray mold neck rot 
                 ( Botrytis allii ) 
               
               
                 Strawberry 
               
               
                 Powdery mildew 
                 ( Sphaerotheca humuli ) 
               
               
                 Gray mold 
                 ( Botrytis cinerea ) 
               
               
                 Apple 
               
               
                 Powdery mildew 
                 ( Podosphaera leucotricha ) 
               
               
                 Scab 
                 ( Venturia inaequalis ) 
               
               
                 Blossow blight 
                 ( Monilinia mali ) 
               
               
                 Persimmon 
               
               
                 Anthracnose 
                 ( Gloeosporium kala ) 
               
               
                 Peach 
               
               
                 Brown rot 
                 ( Monilinia fructicola ) 
               
               
                 Grape 
               
               
                 Powdery mildew 
                 ( Uncinula necator ) 
               
               
                 Downy mildew 
                 ( Plasmopara viticola ) 
               
               
                 Gray mold 
                 ( Botrytis cinerea ) 
               
               
                 Pear 
               
               
                 Rust 
                 ( Gymnosporangium asiaticum ) 
               
               
                 Black spot 
                 ( Alternaria kikuchiana ) 
               
               
                 Tea-plant 
               
               
                 Leaf spot 
                 ( Pestalotia theae ) 
               
               
                 Anthracnose 
                 ( Colletotrichum theae-sinensis ) 
               
               
                 Orange 
               
               
                 Scab 
                 ( Elsinoe fawcetti ) 
               
               
                 Blue mold 
                 ( Penicillium italicum ) 
               
               
                 Turf 
               
               
                 Sclerotinia snow blight 
                 ( Sclerotinia borealis ) 
               
               
                   
               
             
          
         
       
     
     In recent years, it is known that various pathogenic fungi have developed their resistance to benzimidazole fungicides and ergosterol biosynthesis inhibitors and that such fungicides have been insufficient in their fungicidal effectiveness. Therefore, it is required to provide new compounds useful as a fungicide which are effective to the resistant-strain of such pathogenic fungi as well. The compounds of the present invention are the ones which can be a fungicide having excellent fungicidal effectiveness not only to the acceptible-strains of pathogenic fungi but also to the resistant-strains of pathogenic fungi to benzinidazole fungicides and ergosterol biosynthesis inhibitors. 
     The compounds of the present invention can be utilized as an antifouling agent for preventing the adhesion of aqueous organisms to structures, such as the bottom of a ship and fishing nets, in water and sea. 
     Also, the compounds of the present invention can be contained in paints and fibers and thereby used as an antimicrobial agent for walls, bathtubs, shoes and clothes. 
     Furthermore, some of the compounds of the present invention can show insecticidal, acaricidal and herbicidal activities. 
     In the practical application of the compounds of the present invention obtained as described above, the compounds can be used in the state as it is without formulation, or, for the use as agricultural plant protection chemicals, the compounds can be applied in forms of general formulations for agricultural plant protection chemicals, such as wettable powders, granules, powders, emulsifiable concentrates, aqueous solutions, suspensions and flowables. For the additives and carriers to be used in the formulations described above, vegetable powders, such as soybean powder and wheat powder, mineral fine powders, such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite and clay, and organic and inorganic compounds, such as sodium benzoate, urea and Glauber&#39;s salt, can be used, when the compounds are formulated into solid formulations. Whereas, when the compounds are formulated into liquid formulations, petroleum fractions, such as kerosine, xylene and solvent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohols, acetone, trichloro ethylene, methylisobutyl ketone, mineral oils, vegetable oils and water, can be used as the solvent. In these formulations, surface active agents may be added to the formulations in order to make the formulations homogeneous and stable, if appropriate. 
     The content of the compound of the present invention as the active principle in the formulations is preferably in a range of from 5 to 70%. 
     The wettable powders, the emulsifiable concentrates and the flowable formulation comprising the compound of the present invention prepared as described above can be applied in a form prepared by diluting the formulations with water to the suspension or the emulsion at a desired concentrations, while the powders and the granules of the said compound can be directly applied to plants without dilution. 
     The compounds of the present invention can demonstrate sufficient effectiveness on plant diseases independently; however, it is also possible to use the said compound in admixing with 1 or more of other fungicides, insecticides, acaricides or synergists. 
     The followings are the examples for the fungicides, insecticides, acaricides, nematocides and plant growth regulators, those which are usable in admixing with the compounds of the present invention. 
     Fungicides 
     Copper-Based Fungicides 
     Basic copper chloride, basic copper sulfate, etc. 
     Sulphur-based Fungicides 
     Thiram, maneb, mancozeb, polycarbamate, propineb, ziram, zineb, etc. 
     Polyhaloalkylthio Fungicides 
     Captan, dichlofluanid, folpet, etc. 
     Organochlorine Fungicides 
     Chlorothalonil, fthalide, etc. 
     Organophosphorous Fungicides 
     IBP, EDDP, tolcolofos-methyl, pyrazophos, fosetyl-Al, etc. 
     Benzimidazole Fungicides 
     Thiophanate-methyl, benomyl, carbendazim, thiabendazole, etc. 
     Dicarboxyimide Fungicides 
     Oxycarboxine, mepronyl, flutolanil, techlofthalam, trichiamide, pencycuron, etc. 
     Acyl Alanine Fungicides 
     Metalaxyl, oxadixyl, furalaxyl etc. 
     EBI Fungicides 
     Triadimefon, triadomenol, bitertanol, microbutanil, hexaconazol, propiconazole, triflumizole, procloraz, peflazoate, fenarimol, pyrifenox, trifolin, flusilazole, etaconazole, diclobutrazol, fluotrimazole, flutriafen, penconazole, diniconazole, cyproconazole, imazalil, tridemorph, fenpropimorph, buthiobate, etc. 
     Antibiotics 
     Polyoxin, blasticidin-S, kasugamycin, validamycin, streptomycin sulfate, etc. 
     Others 
     Propamocarb hydrochloride salt, quintozene, hydroxyisoxazole, metasulfocarb, anilazine, isoprothiolane, probenazole, quinomethionate, dithianone, dinocap, dichlomezine, mepaniprim, ferimzone, fluazinam, pyroquilon, tricyclazole, oxolinic acid, dithianone, iminoctazine acetate salt, cymoxanil, pyrrolenitrine, metasulfocarb, diethofensarb, binapacryl, lecithin, sodium hydrogencarbonate, fenaninosulf, dodine, dimnethomorph, fenazine oxide, etc. 
     Insecticides and Acaricides 
     Organophosphorous and Carbamate Insecticides 
     Fenthion, fenitrothion, diazinon, chlorpyrifos, ESP, vamidothion, fenthoate, dimethoate, formothion, malathon, trichlorfon, thiometon, phosmet, dichlorvos, acephate, EPBP, methyl parathion, oxydimeton methyl, ethion, salithion, cyanophos, isoxathion, pyridafenthion, phosalon, methydathion, sulprofos, chlorfenvinphos, tetrachlorvinphos, dimethylvinphos, propaphos, isofenphos, ethylthiometon, profenofos, pyraclophos, monocrotophos, azinphos methyl, aldicarb, methomyl, thiodicarb, carbofuran, carbosulfan, benfuracarb, furathiocarb, propoxur, BPMC, MTMC, MIPC, carbaryl, pirimicarb, ethiofencarb, fenoxycarb, cartap, thiocyclam, bensultap, etc. 
     Pyrethroid Insecticides 
     Permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropathrin, pyrethrin, allethrin, tetramethrin, resmethrin, dimethrin, propathrin, fenothrin, prothrin, fluvalinate, cyfluthrin, cyhalothrin, flucythrinate, ethofenprox, cycloprothrin, tralomethrin, silafluophen, brofenprox, acrinathrin, etc. 
     Benzoyl Urea-Based Insecticides and Others: 
     Diflubenzuron, chlorfluazuron, hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen, methoprene, benzoepin, diaphenthiuron, imidacloprid, fipronil, nicotine sulfate, rotenone, meta-aldehyde, machine oil  Bacillus thuringiensis , microbial insecticides such as insect-pathogenic viruses, etc. 
     Nematocides 
     Fenamiphos, phosthiazate, etc. 
     Acaricides 
     Chlorbenzilate, phenisobromolate, dicofol, amitra BPPS, benzomate, hexythiazox, fenbutatin oxide, polynactin, quinomethionate, CPCBS, tetradifon, avermectin, milbemectin, chlofentezin, cyhexatin, pyridaben, fenpyroxymate, tebufenpyrad, pyrimidifen, fenothiocarb, dienochlor, etc. 
     Plant Growth Regulators 
     Gibberellines (Gibberelline A 3 , Gibberelline A 4 , Gibberelline A 7 , etc.), IAA, and NAA. 
     EXAMPLES 
     The following examples serve to provide further appreciation of the invention but are not meant in any way to restrict the effective scope of the invention. The structures of isolated novel compounds were confirmed by NMR, Mass, and/or other appropriate analysis. 
     Example 1 
     5-Bromo-2-methylthio-6-trifluoromethyl-3H-pyrimidin-4-one 
     2-Methylthio-4-trifluoromethyl-3H-pyrimidin-4-one (20.0 g). was dissolved in acetonitrile (100 ml) and N-bromosuccinimide (18.7 g) was added at room temperature with stirring. The mixture was refluxed fbr 5 hr and the solvent was removed under reduced pressure. The precipitates were mixed with water, filtered off and dried. The solid thus obtained was mixed with hot hexane and filtered off to give 5-bromo-2-methylthio-6-trifluoromethyl-3H-pyrimidin-4-one (25.3 g) as colorless needles, mp 215-216° C. 
     Example 2 
     5-Iodo-2-isopropylthio-6-trifluoromethyl-3H-pyrimidin-4-one 
     2-Isopropylthio-6-trifluoromethyl-3H-pyrimidin-4-one (23.3 g) was dissolved in acetonitrile (230 ml) and N-iodosuccinimide (24.2 g) was added at room temperature with stirring. The mixture was refluxed for 2.5 hr and the solvent was removed under reduced pressure. The precipitates were dissolved in ethyl acetate, and then washed with aqueous sodium thiosulfate, water and brine, respectively. The ethyl acetate layer was dried over magnesium sulfite and the solvent was removed under reduced pressure to give 5-iodo-2-isopropylthio-6-trifluoromethyl-3H-pyrimidin-4-one (34.8 g) as pale yellow needles, mp 212-215° C. 
     Example 3 
     5-Iodo-2-(pyridin-2-yl)-6-trifluoromethyl-3H-pyrimidin-4-one 
     2-(Pyridin-2-yl)-6-trifluoromethyl-3H-pyrimidin-4-one (15.0 g) was dissolved in DMP (150 ml) and N-iodosuccinimide (33.6 g) was added at room temperature with stirring. The mixture was stirred under heating (130-135° C.) for 6 hr. and then cooled to room temperature. The reaction mixture was added ethyl acetate (150 ml), and then washed with aqueous sodium thiosulfate, water and brine, respectively. The ethyl acetate layer was dried over magnesium sulfate and the solvent was removed under reduced pressure to give crude 5-iodo-2-(pyridine-2-yl)-6-trifluoromethyl-3H-pyrimidin-4-one. It was recrystallized from toluene as pale brown needles (10.2 g), mp 186-187° C. 
     Example 4 
     4-Chloro-5-iodo-2-methylthio-6-trifluoromethylpyrimidine 
     5-Iodo-2-methylthio-6-trifluoromethyl-3H-pyrimidin-4-one (11.8 g) was dissolved in phosphoryl chloride (40 ml) and phosphorous pentachloride (7.9 g) was added at room temperature with stirring. The mixture was refluxed for 3 hr and the phosphoryl chloride was removed under reduced pressure. The residue was poured onto icy water and extracted with chloroform. The chloroform layer was washed with water and brine, respectively and dried over magnesium sulfate. The solvent was removed under reduced pressure to give 4-chloro-5-iodo-2-methylthio-6-trifluoromethylpyrimidine (12.2 g) as pale brown crystalline solid, mp 55-56° C. 
     Example 5 
     4-Chloro-5-iodo-2-isopropylsulfonyl-6-trifluoromethypyrimidine 
     4-Chloro-5-iodo-2-isopropylthio-6-trifluoromethypyrimidine (15.0 g) was dissolved in dichloromethane (150 ml) and m-chloroperbenzoic acid (75%, 27.1 g) was added portionwise under ice cooling with stirring. After stirring over night at room temperature, precipitated solid (m-chlorobenzoic acid) was removed by filtration. The reaction mixture was added aqueous sodium thiosulfate dropwise under ice cooling, then precipitated solid (m-chlorobenzoic acid) was removed by filtration again. The water layer was separated, and the dichloromethane layer was washed with aqueous sodium bicarbonate and brine, respectively and dried over magnesium sulfate. The solvent was removed under reduced pressure to give 4-chloro-5-iodo-2-isopropylsulfonyl-6-trifluoromethypyrimidine (14.3 g) as pale yellow crystalline solid, mp 67-69° C. 
     Example 6 
     5-Iodo-4-methoxy-2-methyl-6-trifluoromethylpyrimidine 
     4-Chloro-5-iodo-2-methyl-6-trifluoromethylpyrimidine (23.0 g) was dissolved in methanol (150 ml) and sodium methoxide (30% methanol solution, 12.8 g) was added under ice cooling with stirring. After stirring over night at room temperature, the solvent was removed under reduced pressure. The residue was mixed with water and extracted with benzene, and then benzene layer was washed with water and brine, respectively and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate). The crude fraction was concentrated, and then washed with cold hexane to give 5-iodo-4-methoxy-2-methyl-6-trifluoromethylpyrimidine (13.0 g) as colorless crystalline solid, mp 44-45° C. 
     Example 7 
     5-Ethynyl-4-methoxy-2-methylt-6-trifluoromethylpyrimidine 
     5-Iodo-4-methoxy-2-methyl-6-trifluoromethylpyrimidine (5.0 g) was dissolved in DMF (50 ml) and N,N-diisopropylethylamine (6.5 g), copper(I) iodide (0.3 g), dichlorobis(triphenylphosphine)palladium(II) (1.12 g) and trimethylsilylacetylene (15.4 g) was added at room temperature with stirring. The mixture was heated (50° C.) in nitrogen atmosphere for 7 hr and cool to room tempeature. The reaction mixture was added methyl tert-butyl ether (MTBE) (200 ml). The insoluble matter was removed by filtration through Celite and the filtrate was washed with water and brine, respectively. The MTBE solution was dried over magnesium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give crude 4-methoxy-2-methyl-6-trifluoromethyl-5-trimethylsilylethynylpyrimidine (5.3 g) as pale yellow oil. This crude 4-methoxy-2-methyl-6-trifluoromethyl-5-trimethylsilylethynylpyrimidine (5.2 g) was dissolved in THF (100 ml) and tetrabutylammonium fluoride (1M THF solution, 18 ml) was added under ice cooling with stirring. After stirring 30 min at this temperature, the reaction mixture was added water in one portion under ice cooling and extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine, respectively and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane ethyl acetate) to give 5-ethynyl-4-methoxy-2-methyl-6-trifluoromethylpyrimidine (1.92 g) as colorless crystalline solid, mp 77° C. 
     Example 8 
     5-(1-Chlorovinyl)-2-methyl-6-trifluoromethyl-3H-pyrimidin-4-one 
     5-ethynyl-4-methoxy-2-methyl-6-trifluoromethylpyrimidine (1.92 g) was added 6N-HCl (20 ml) with stirring and refluxed for 2 hr. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with brine and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexanethyl acetate). The crude fraction was concentrated, and then washed with hexane to give 5-(1-chlorovinyl)-2-methyl-6-trifluoromethyl-3H-pyrimidin-4-one (1.62 g) as colorless crystalline solid, mp 164-166° C. 
     Example 9 
     5-Fluoro-2,4-dimethoxy-6-trifluoromethypyrimidine 
     5-Bromo-2,4-dimethoxy-6-trifluoromethypyrimidine (0.50 g) was dissolved in dry THF (5 ml) at room temperature under nitrogen atmosphere. The mixture was cooled to −70° C., and then added n-butyllithium (1.6M in hexane, 1.2 ml) dropwise below −50° C., and then added N-fluoro-bisphenylsulfonimide (0.61 g) TBF (5 ml) solution at once and the temperature was raised up to room temperature and then added water. The reaction mixture was extacted with benzene. The benzene layer was washed with water and brine, respectively and dried over magnesium sulfate. The solvent was removed under reduced pressure to give 5-fluoro-2,4-dimethoxy-6-trifluoromethypyrimidine (0.30 g) as pale yellow oil, ESI-MS 227 [M+H] + . 
     Example 10 
     4-Cyano-5-iodo-2-methylthio-6-trifluoromethylpyrimidine 
     4-Chloro-5-iodo-2-methylthio-6-trifluoromethylpyrimidine (5.00 g) was dissolved in propionitrile (125 ml) and 4-(dimethylamino)-pyridine (1.81 g) was added at room temperature with stirring. After several minutes, precipitates appeared, however, it was stirred over night at room temperature. The slurry was cooled to ice bath temperature, and then added sodium cyanide (1.04 g) water (10 ml) solution. The mixture was warmed to room temperature and stirred 3 hr. The reaction mixture was added water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine, respectively and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica get column chromatography (hexane-ethyl acetate) to give 4-cyano-5-iodo-2-methylthio-6-trifluoromiethylpyrimidine (2.56 g) as yellow solid, mp 68-69° C. 
     Example 11 
     4-Imidazol-1-yl-5-iodo-2-isopropylthio-6-trifluoromehyl-pyrimidine 
     4-Chloro-5-iodo-2-isopropylthio-6-trifluoromethylpyrimidine (3.0 g) was dissolved in acetonitrile (30 ml) and imidazole (1.6 g) was added at room temperature with stirring. The mixture was refluxed fbr 3 hr and then the solvent was removed under reduced pressure. The residue was added water and precipitates was filtered off to give crude 4-imidazol-1-yl-5-iodo-2-isopropylthio-6-trifluoromethyl-pyrimidine. It was recryslized from methanol-water mixture as colorless needles (2.61 g), mp 118-120° C. 
     Example 12 
     Ethyl 1-(5-iodo-2-isopropylthio-6-trifluororethylpyrimidin-4-yl)-3-trifluoromethyl-1H-pyrazol-4-carboxylate 
     4-Chloro-5-iodo-2-isopropylthio-6-trifluoromethylpyrimidine (0.30 g) was dissolved in dimethylsulfoxide (3.0 ml) and ethyl 3-trifluoromethyl-1H-pyrazole-4-carboxylate (0.16 g) and 1,8-diazabicyclo-[5,4,0]-under-7-ene (0.12 g) was added at room temperature with stirring. The mixture was heated to 80° C. and stirred for 2 hr. After cooling to room temperature, the mixture was added water and extracted with benzene. The benzene layer was washed with water and brine, respectively and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give ethyl 1-(5-iodo-2-isopropylthio-6-trifluoromethylpyrimidin-4-yl)-3-trifluoromethyl-1H-pyrazole-4-carboxylate (0.30 g) as colorless crystalline solid, mp 107-108° C. 
     Example 13 
     4-Imidazol-1-yl-5-iodo-2-prop-2-ynyloxy-6-trifluoromethyl-pyrimidine 
     4-Chloro-5-iodo-2-isopropylsulfonyl-6-trifluoromethypyrimidine (0.79 g) was dissolved in tetrahydrofuran (5.0 ml) and added propargyl alcohol (0.11 g). The mixture was cooled to ice bath temperature and added sodium hydride (oily 80%, 57 mg). The mixture was stirred at that temperature for 10 minutes, and then added imidazole (0.39 g) at the same temperature. The mixture was stirred at that temperature for 30 minutes, and then it warmed to room temperature. After stirring over night, the mixture was added water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine, respectively and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-THF). The fraction was triturated by hexane to give 4-imidazol-1-yl-5-iodo-2-prop-2-ynyloxy-6-trifluoromethyl-pyrimidine (0.20 g) as colorless crystalline solid, mp 128-129° C. 
     Example 14 
     1-(4-Imidazol-1-yl-5-iodo-6-trifluoromethylpyrimidin-2-yl)-pyrrolidin-2-one 
     4-Chloro-5-iodo-2-isopropylsulfonyl-6-trifluoromethypyrimidine (0.50 g) was dissolved in tetrahydrofuran (5.0 ml) and added 2-pyrrolidinone (0.10 g). The mixture was cooled to ice bath temperature and added sodium hydride (oily 80%, 36 mg). The mixture was stirred at that temperature for 10 minutes, and then added imidazole (0.25 g) at the same temperature. The mixture was stirred at that temperature for 30 minutes, and then it warmed to room temperature After stirg over night, the mixture was added water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine, respectively and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-THF) to give 1-(4-imidazol-1-yl-5-iodo-6-trifluoromethylpyrimidin-2-yl)-pyrrolidin-2-one (0.20 g) as colorless crystalline solid, mp 195-197° C. 
     Example 15 
     5-Iodo-2-methylthio-4-(2H-tetrazol-5-yl)-6-trifluoromethyl-pyrimidine 
     4-Cyano-5-iodo-2-methylthio-6-trifluoromethylpyrimidine (0.50 g) was dissolved in isopropanol (5 ml) and added water (10 ml), sodium azide (0.19 g) and zinc bromide (0.16 g) with stirring in room temperature. The mixture was refluxed for 3 hr and then cooled to room temperature and then added 3N-HCl to acidify. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine, respectively and dried over magnesium sulfate. The solvent was removed under reduced pressure to give 5-iodo-2-methylthio-4-(2H-tetrazol-5-yl)-6-trifluoromethyl-pyrimidine (0.5 g) as colorless crystalline solid, mp 196-200° C. 
     Example 16 
     5-Iodo-2-methylthio-4-(2-methyl-2H-tetrazol-5-yl)-6-trifluoromethyl-pyrimidine 
     5-Iodo-2-methylthio-4-(2H-tetrazol-5-yl)trifluoromethyl-pyrimidine (0.25 g) was added benzene (4 ml) and methanol (1 ml). The mixture was added trimethylsilyldiazomethane (2M in hexane, 1 ml) at room temperature dropwise and stirred over night. The solvent was removed under reduced pressure to give crude 5-iodo-2-methylthio-4-(2-methyl-2H-tetrazol-5-yl)-4-trifluoromethyl-pyrimidine. It was recrystallized from hexane-benzene as colorless crystalline solid, mp 113-118° C. 
     Example 17 
     5-(1-Chlorovinyl)-4-imidazol-1-yl-2-methyl-6-trifluoromethyl-pyrimidine 
     4-Chloro-5-(1-chlorovinyl)-2-methyl-6-trifluoromethylpyrimidine (1.83 g) was dissolved in acetonitrile (20 ml) under stirring in room temperature. The mixture was added imidazole (1.45 g) and refluxed 3 hr and then cooled to room temperature and added water. The mixture was extracted with chloroform. The chloroform layer was washed with water and brine, respectively and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-THF) to give 5-(1-chlorovinyl)-4-imidazol-1-yl-2-methyl-6-trifluoromethyl-pyrimidine (1.34 g) as pale brown oil.  1 H-NMR (δ, ppm); 2.82 (s, 3H), 5.78 (d, 1H), 6.03 (d, 1H), 7.21 (br, 1H), 7.87 (br, 1H), 8.55 (br, 1H). 
     Example 18 
     5-Ethynyl-4-imidazol-1-yl-2-methyl-6-trifluoromethylpyrimidine 
     5-(1-Chlorovinyl)-4-imidazol-1-yl-2-methyl-6-trifluoromethyl-pyrimidine (0.20 g) was dissolved in dimethylsulfoxide (2 ml) and 1,8-diazabicyclo-[5,4,0]-undec-7-ene (0.11 g) was added at room temperature with stirring. The mixture was stirred for 2 hr in room temperature and then added water. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed water and brine, respectively and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-THF) to give 5-Ethynyl-4-imidazol-1-yl-2-methyl-6-trifluoromethylpyrimidine (0.11 g) as colorless crystalline solid, mp 121-122° C. 
     Example 19 
     5-Fluoro-2,4-diimidazol-1-yl-6-trifluoromethylpyrimidine 
     2,4-Dichloro-5-fluoro-6-trifluoromethylpyrimidine (2.74 g) was dissolved in acetonitrile (30 ml) and imidazole (3.97 g) was added at room temperature with stirring. The mixture was stirred over night and then the solvent was removed under reduced pressure. The residue was added water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine, respectively and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was triturated with carbon tetrachloride to give crude, 5-fluoro-2,4-diimidazol-1-yl-6-trifluoromethylpyrimidine. It was recrystallized from isopropanol as colorless crystalline solid, mp 142-150° C. (decomposed). 
     Test Example 1 
     Test on Apple Scab Control (Preventive Application) 
     The emulsifiable concentrate prepared for the compound according to the present invention was diluted so as to prepared the solution at a concentration of 100 ppm, and the diluted solution was the sprayed to apple young trees (variety, Kokko, at 3-4 leaf stage) grown in an unglazed pot. The spayed solution was naturally dried, then conidia of apple scab fungus ( Venturia inaequalis ) were inoculated onto the test apples. The inoculated apple trees were placed in a room being maintained at 20° C. and high humidity with repeated lighting of 12 hours intervals, and the apple trees are allowed to stand in the room for two weeks. After that period, assessment was made to determine the control efficacy by checking the infestation degree by the fungus on the leaves in comparison with the control apple trees. As a result, the compounds having the following compound numbers showed to have excellent control performance value higher than 75% on the disease. Note that the compound numbers in the following correspond to the same compound numbers in the Table 1. 
     Compound Nos.; 47, 48, 54, 68, 78, 86, 90, 128, 145, 238, 256, 274, 292, 328, 346, 401, 474, 531, 568, 586 
     Test Example 2 
     Test on Kidney Bean Gray Mold Control 
     Flowers of Kidney bean (variety; Nagauzura) grown in a flat vessel for culturing seedlings were cut, and the cut flowers were dipped into a solution prepared by diluting the emulsifiable concentrate prepared fbr the compound of the present invention at a concentration of 100 ppm based on the active ingredient. After the dipping, the flowers were dried at a room temperature. Then, spore solution of snap bean gray mold fuingus ( Botrytis cinerea ) was sprayed to the flowers. The flowers sprayed with spores of the gray mold fungus were placed on the leaves which were detached from healthy Kidney bean plants, and those leaves were placed in a room being maintained at 20° C. and high humidity with repeated lighting of 12 hours intervals, and the Kidney bean leaves were incubated in the room for 7 days. Then, the infestation degree by the fungus on the leaves was checked in comparison to the control healthy leaves to determine the control efficacy. As a result, the compounds of the following compound numbers showed to have excellent control performance. Note that the compound numbers in the following correspond to the same compound numbers in the Table 1. 
     Compound Nos.; 47, 48, 54, 68, 90, 184, 238, 256, 274, 292, 531, 568 
     Test Example 3 
     Test on  Pythium aphanidermatum  “In Vitro” Control of Growth 
     The compound was prepared according to the present invention was diluted to achieve a final concentration of 100 ppm, and the diluted solution was used to saturate ½ inch-diameter, cellulose discs (Schleicher &amp; Schuell catalog #740-E). The treated cellulose discs were then air dried for 90 minutes in a class 11 biosafety cabinet to eliminate external free moisture. Replicated treated discs and untreated discs were placed onto Difco Corn meal agar in 80 mm plastic petri plates. The discs (2 treated and one untreated in each of two petri plates) were each inoculated with a 4 mm square block of agar containing an actively growing culture of  Pythium aphanidermatum . The inoculated plates were incubated at 23° C. with diurnal lighting with 12 hour intervals. Radial growth of  Pythium aphanidermatum  on the treated and untreated discs was measured at 24 and 48 hours after inoculation. Percent of growth inhibition was determined by comparing radial growth on the untated check discs to the growth on the treated discs. As a result, the compounds listed below had an excellent suppression performance value compared to the untreated check. Note that the compound numbers listed below correspond to the same compound numbers in Table 1. 
     Compound Nos.; 1, 47, 256, 346, 401, 474, 531, 586 
     Test Example 4 
     Test on  Sclerotinia sclerotiorum  “In Vitro” Control of Growth 
     The compound prepared according to the present invention was diluted to achieve a final concentration of 100 ppm, and the diluted solution was used to satrate ½ inch-diameter, cellulose discs (Schleicher &amp; Schuell catalog #740-E). The treated cellulose discs were then air dried for 90 minutes in a class II biosafety cabinet to eliminate external free moisture. Replicated treated discs and untreated discs were placed onto acidified Difco Potato Dextrose agar in 80 mm plastic petri plates. The discs (2 treated and one untrtated in each of two petri plates) were each inoculated with a 4 mm square block of agar containing an actively growing culture of  Sclerotinia sclerotiorum . The inoculated plates were incubated at 23° C. with diurnal lighting with 12 hour intervals. Radial growth of  Sclerotinia sclerotiorum  on the treated and untreated discs was measured at 48 and 96 hours after inoculation. Percent of growth inhibition was determined by comparing radial growth on the untreated check discs to the growth on the treated discs. As a result, the compounds listed below had an excellent suppression performance value compared to the untreated check. Note that the compound numbers listed below correspond to the same compound numbers in Table 1. 
     Compound Nos. 1, 47, 48, 128, 145, 256, 401, 474, 531, 568, 586 
     
       
         
               
               
             
               
               
               
               
               
               
             
               
               
               
               
               
               
             
           
               
                 TABLE 1 
               
             
             
               
                   
               
               
                   
                 (1) 
               
               
                 
                   
                             
                     
                         
                         
                     
                   
                 
               
               
                   
               
             
          
           
               
                 No. 
                 R1 
                 R2 
                 R3 
                 Q 
                 mp (° C.) 
               
               
                   
               
             
          
           
               
                 1 
                 SCH3 
                 CF3 
                 I 
                 1,2,4-triazol-1-yl 
                 93-94 
               
               
                 2 
                 SCH3 
                 CF2CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 3 
                 SCH3 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
                 196-200 
               
               
                   
                   
                   
                   
                   
                 dec 
               
               
                 4 
                 SCH3 
                 CF2CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 5 
                 SCH3 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
                 113-118 
               
               
                 6 
                 SCH3 
                 CF2CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 7 
                 SCH3 
                 CF3 
                 I 
                 3-(p-acetoxybenzylthio)-1,2,4-triazol-1-yl 
               
               
                 8 
                 SCH3 
                 CF3 
                 I 
                 3-amino-1,2,4-triazol-1-yl 
               
               
                 9 
                 SCH3 
                 CF3 
                 I 
                 3-bromo-1,2,4-triazol-1-yl 
               
               
                 10 
                 SCH3 
                 CF3 
                 I 
                 3-chloro-1,2,4-triazol-1-yl 
               
               
                 11 
                 SCH3 
                 CF3 
                 I 
                 3-cyano-1,2,4-triazol-1-yl 
               
               
                 12 
                 SCH3 
                 CF3 
                 I 
                 3-fluoro-1,2,4-triazol-1-yl 
               
               
                 13 
                 SCH3 
                 CF3 
                 I 
                 3-hydroxy-1,2,4-triazol-1-yl 
               
               
                 14 
                 SCH3 
                 CF3 
                 I 
                 3-mercapto-1,2,4-triazol-1-yl 
               
               
                 15 
                 SCH3 
                 CF3 
                 I 
                 3-methoxy-1,2,4-triazol-1-yl 
               
               
                 16 
                 SCH3 
                 CF3 
                 I 
                 3-methylamino-1,2,4-triazol-1-yl 
               
               
                 17 
                 SCH3 
                 CF3 
                 I 
                 3-methylthio-1,2,4-triazol-1-yl 
               
               
                 18 
                 SCH3 
                 CF3 
                 I 
                 3-trifluoromethyl-1,2,4-triazol-1-yl 
               
               
                 19 
                 SCH3 
                 CF3 
                 I 
                 5-(p-acetoxybenzylthio)imidazol-1-yl 
               
               
                 20 
                 SCH3 
                 CF3 
                 I 
                 5-(p-acetoxybenzylthio)-1,2,4-triazol-1-yl 
                 141-143 
               
               
                 21 
                 SCH3 
                 CF3 
                 I 
                 4-aminoimidazol-1-yl 
               
               
                 22 
                 SCH3 
                 CF3 
                 I 
                 5-amino-1,2,4-triazol-1-yl 
               
               
                 23 
                 SCH3 
                 CF3 
                 I 
                 4-bromoimidazol-1-yl 
               
               
                 24 
                 SCH3 
                 CF3 
                 I 
                 5-bromo-1,2,4-triazol-1-yl 
               
               
                 25 
                 SCH3 
                 CF3 
                 I 
                 4-chloroimidazol-1-yl 
               
               
                 26 
                 SCH3 
                 CF3 
                 I 
                 5-chloro-1,2,4-triazol-1-yl 
               
               
                 27 
                 SCH3 
                 CF3 
                 I 
                 4-cyanoimidazol-1-yl 
               
               
                 28 
                 SCH3 
                 CF3 
                 I 
                 5-cyano-1,2,4-triazol-1-yl 
               
               
                 29 
                 SCH3 
                 CF3 
                 I 
                 4-fluoroimidazol-1-yl 
               
               
                 30 
                 SCH3 
                 CF3 
                 I 
                 5-fluoro-1,2,4-triazol-1-yl 
               
               
                 31 
                 SCH3 
                 CF3 
                 I 
                 4-hydroxyimidazol-1-yl 
               
               
                 32 
                 SCH3 
                 CF3 
                 I 
                 5-hydroxy-1,2,4-triazol-1-yl 
               
               
                 33 
                 SCH3 
                 CF3 
                 I 
                 4-mercaptoimidazol-1-yl 
               
               
                 34 
                 SCH3 
                 CF3 
                 I 
                 5-mercapto-1,2,4-triazol-1-yl 
               
               
                 35 
                 SCH3 
                 CF3 
                 I 
                 4-methoxyimidazol-1-yl 
               
               
                 36 
                 SCH3 
                 CF3 
                 I 
                 5-methoxy-1,2,4-triazol-1-yl 
               
               
                 37 
                 SCH3 
                 CF3 
                 I 
                 4-methylaminoimidazol-1-yl 
               
               
                 38 
                 SCH3 
                 CF3 
                 I 
                 5-methylamino-1,2,4-triazol-1-yl 
               
               
                 39 
                 SCH3 
                 CF3 
                 I 
                 4-methylimidazol-1-yl 
                 147-148 
               
               
                 40 
                 SCH3 
                 CF2CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 41 
                 SCH3 
                 CF3 
                 I 
                 4-methylthioimidazol-1-yl 
               
               
                 42 
                 SCH3 
                 CF3 
                 I 
                 5-methylthio-1,2,4-triazol-1-yl 
               
               
                 43 
                 SCH3 
                 CF3 
                 I 
                 4-trifluoromethylimidazol-1-yl 
               
               
                 44 
                 SCH3 
                 CF3 
                 I 
                 5-trifluoromethyl-1,2,4-triazol-1-yl 
               
               
                 45 
                 SCH3 
                 CF3 
                 I 
                 benzimidazol-1-yl 
                 128 
               
               
                 46 
                 SCH3 
                 CF2CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 47 
                 SCH3 
                 CF3 
                 I 
                 imidazol-1-yl 
                 137-139 
               
               
                 48 
                 SCH3 
                 CF2CF3 
                 I 
                 imidazol-1-yl 
                 112-114 
               
               
                 49 
                 SCH3 
                 CF3 
                 I 
                 pyrazol-1-yl 
                 115-116 
               
               
                 50 
                 SCH3 
                 CF3 
                 F 
                 2H-tetrazol-5-yl 
               
               
                 51 
                 SCH3 
                 CF3 
                 F 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 52 
                 SCH3 
                 CF3 
                 Cl 
                 2H-tetrazol-5-yl 
                 177-178 
               
               
                 53 
                 SCH3 
                 CF3 
                 Cl 
                 2-methyl-2H-tetrazol-5-yl 
                 128-130 
               
               
                 54 
                 SCH3 
                 CF3 
                 Br 
                 1,2,4-triazol-1-yl 
                 85-87 
               
               
                 55 
                 SCH3 
                 CF3 
                 Br 
                 2H-tetrazol-5-yl 
                 192-193 
               
               
                 56 
                 SCH3 
                 CF3 
                 Br 
                 2-methyl-2H-tetrazol-5-yl 
                 102-105 
               
               
                 57 
                 SCH3 
                 CF3 
                 Br 
                 imidazol-1-yl 
                 89-90 
               
               
                 58 
                 SCH2CH3 
                 CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 59 
                 SCH2CH3 
                 CF2CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 60 
                 SCH2CH3 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 61 
                 SCH2CH3 
                 CF2CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 62 
                 SCH2CH3 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 63 
                 SCH2CH3 
                 CF2CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 64 
                 SCH2CH3 
                 CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 65 
                 SCH2CH3 
                 CF2CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 66 
                 SCH2CH3 
                 CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 67 
                 SCH2CH3 
                 CF2CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 68 
                 SCH2CH3 
                 CF3 
                 I 
                 imidazol-1-yl 
                 106-109 
               
               
                 69 
                 SCH2CH3 
                 CF2CF3 
                 I 
                 imidazol-1-yl 
               
               
                 70 
                 SCH2CH3 
                 CF3 
                 F 
                 2H-tetrazol-5-yl 
               
               
                 71 
                 SCH2CH3 
                 CF3 
                 F 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 72 
                 SCH2CH3 
                 CF3 
                 Cl 
                 2H-tetrazol-5-yl 
               
               
                 73 
                 SCH2CH3 
                 CF3 
                 Cl 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 74 
                 SCH2CH3 
                 CF3 
                 Br 
                 2H-tetrazol-5-yl 
               
               
                 75 
                 SCH2CH3 
                 CF3 
                 Br 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 76 
                 SCH(CH3)2 
                 CF3 
                 I 
                 1,2,3-triazol-1-yl 
                 157-159 
               
               
                 77 
                 SCH(CH3)2 
                 CF3 
                 I 
                 1,2,3-triazol-2-yl 
                 167-169 
               
               
                 78 
                 SCH(CH3)2 
                 CF3 
                 I 
                 1,2,4-triazol-1-yl 
                 70-71 
               
               
                 79 
                 SCH(CH3)2 
                 CF2CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 80 
                 SCH(CH3)2 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 81 
                 SCH(CH3)2 
                 CF2CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 82 
                 SCH(CH3)2 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 83 
                 SCH(CH3)2 
                 CF2CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 84 
                 SCH(CH3)2 
                 CF3 
                 I 
                 2-methylimidazol-1-yl 
                 133-135 
               
               
                 85 
                 SCH(CH3)2 
                 CF3 
                 I 
                 4-ethoxycarbonyl-3- 
                 107-108 
               
               
                   
                   
                   
                   
                 trifluoromethylpyrazol-1-yl 
               
               
                 86 
                 SCH(CH3)2 
                 CF3 
                 I 
                 4-methylimidazol-1-yl 
                 138-140 
               
               
                 87 
                 SCH(CH3)2 
                 CF2CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 88 
                 SCH(CH3)2 
                 CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 89 
                 SCH(CH3)2 
                 CF2CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 90 
                 SCH(CH3)2 
                 CF3 
                 I 
                 imidazol-1-yl 
                 118-120 
               
               
                 91 
                 SCH(CH3)2 
                 CF2CF3 
                 I 
                 imidazol-1-yl 
               
               
                 92 
                 SCH(CH3)2 
                 CF3 
                 F 
                 2H-tetrazol-5-yl 
               
               
                 93 
                 SCH(CH3)2 
                 CF3 
                 F 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 94 
                 SCH(CH3)2 
                 CF3 
                 Cl 
                 2H-tetrazol-5-yl 
               
               
                 95 
                 SCH(CH3)2 
                 CF3 
                 Cl 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 96 
                 SCH(CH3)2 
                 CF3 
                 Br 
                 2H-tetrazol-5-yl 
               
               
                 97 
                 SCH(CH3)2 
                 CF3 
                 Br 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 98 
                 S(O)2CH3 
                 CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 99 
                 S(O)2CH3 
                 CF2CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 100 
                 S(O)2CH3 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 101 
                 S(O)2CH3 
                 CF2CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 102 
                 S(O)2CH3 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 103 
                 S(O)2CH3 
                 CF2CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 104 
                 S(O)2CH3 
                 CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 105 
                 S(O)2CH3 
                 CF2CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 106 
                 S(O)2CH3 
                 CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 107 
                 S(O)2CH3 
                 CF2CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 108 
                 S(O)2CH3 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 109 
                 S(O)2CH3 
                 CF2CF3 
                 I 
                 imidazol-1-yl 
               
               
                 110 
                 S(O)2CH3 
                 CF3 
                 F 
                 2H-tetrazol-5-yl 
               
               
                 111 
                 S(O)2CH3 
                 CF3 
                 F 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 112 
                 S(O)2CH3 
                 CF3 
                 Cl 
                 2H-tetrazol-5-yl 
               
               
                 113 
                 S(O)2CH3 
                 CF3 
                 Cl 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 114 
                 S(O)2CH3 
                 CF3 
                 Br 
                 1,2,4-triazol-1-yl 
                 158-159 
               
               
                 115 
                 S(O)2CH3 
                 CF3 
                 Br 
                 2H-tetrazol-5-yl 
               
               
                 116 
                 S(O)2CH3 
                 CF3 
                 Br 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 117 
                 pyridin-4-yl 
                 CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 118 
                 pyridin-4-yl 
                 CF2CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 119 
                 pyridin-4-yl 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 120 
                 pyridin-4-yl 
                 CF2CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 121 
                 pyridin-4-yl 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 122 
                 pyridin-4-yl 
                 CF2CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 123 
                 pyridin-4-yl 
                 CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 124 
                 pyridin-4-yl 
                 CF2CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 125 
                 pyridin-4-yl 
                 CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 126 
                 pyridin-4-yl 
                 CF2CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 127 
                 pyridin-4-yl 
                 CF2CF3 
                 I 
                 imidazol-1-yl 
               
               
                 128 
                 pyridin-4-yl 
                 CF3 
                 I 
                 imidazol-1-yl 
                 230 
               
               
                   
                   
                   
                   
                   
                 dec 
               
               
                 129 
                 pyridin-4-yl 
                 CF3 
                 F 
                 2H-tetrazol-5-yl 
               
               
                 130 
                 pyridin-4-yl 
                 CF3 
                 F 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 131 
                 pyridin-4-yl 
                 CF3 
                 Cl 
                 2H-tetrazol-5-yl 
               
               
                 132 
                 pyridin-4-yl 
                 CF3 
                 Cl 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 133 
                 pyridin-4-yl 
                 CF3 
                 Br 
                 2H-tetrazol-5-yl 
               
               
                 134 
                 pyridin-4-yl 
                 CF3 
                 Br 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 135 
                 pyridin-2-yl 
                 CF3 
                 I 
                 1,2,4-triazol-1-yl 
                 169-171 
               
               
                 136 
                 pyridin-2-yl 
                 CF2CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 137 
                 pyridin-2-yl 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 138 
                 pyridin-2-yl 
                 CF2CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 139 
                 pyridin-2-yl 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 140 
                 pyridin-2-yl 
                 CF2CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 141 
                 pyridin-2-yl 
                 CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 142 
                 pyridin-2-yl 
                 CF2CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 143 
                 pyridin-2-yl 
                 CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 144 
                 pyridin-2-yl 
                 CF2CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 145 
                 pyridin-2-yl 
                 CF3 
                 I 
                 imidazol-1-yl 
                 243-245 
               
               
                 146 
                 pyridin-2-yl 
                 CF2CF3 
                 I 
                 imidazol-1-yl 
               
               
                 147 
                 pyridin-2-yl 
                 CF3 
                 I 
                 pyrazol-1-yl 
                 145-146 
               
               
                 148 
                 pyridin-2-yl 
                 CF3 
                 F 
                 2H-tetrazol-5-yl 
               
               
                 149 
                 pyridin-2-yl 
                 CF3 
                 F 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 150 
                 pyridin-2-yl 
                 CF3 
                 Cl 
                 2H-tetrazol-5-yl 
               
               
                 151 
                 pyridin-2-yl 
                 CF3 
                 Cl 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 152 
                 pyridin-2-yl 
                 CF3 
                 Cl 
                 imidazol-1-yl 
                 129-130 
               
               
                 153 
                 pyridin-2-yl 
                 CF3 
                 Br 
                 2H-tetrazol-5-yl 
               
               
                 154 
                 pyridin-2-yl 
                 CF3 
                 Br 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 155 
                 pyridin-2-yl 
                 CF3 
                 Br 
                 imidazol-1-yl 
                 140 
               
               
                 156 
                 pyrazol-1-yl 
                 CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 157 
                 pyrazol-1-yl 
                 CF2CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 158 
                 pyrazol-1-yl 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 159 
                 pyrazol-1-yl 
                 CF2CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 160 
                 pyrazol-1-yl 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 161 
                 pyrazol-1-yl 
                 CF2CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 162 
                 pyrazol-1-yl 
                 CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 163 
                 pyrazol-1-yl 
                 CF2CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 164 
                 pyrazol-1-yl 
                 CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 165 
                 pyrazol-1-yl 
                 CF2CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 166 
                 pyrazol-1-yl 
                 CF3 
                 I 
                 imidazol-1-yl 
                 175-180 
               
               
                   
                   
                   
                   
                   
                 dec 
               
               
                 167 
                 pyrazol-1-yl 
                 CF2CF3 
                 I 
                 imidazol-1-yl 
               
               
                 168 
                 pyrazol-1-yl 
                 CF3 
                 F 
                 2H-tetrazol-5-yl 
               
               
                 169 
                 pyrazol-1-yl 
                 CF3 
                 F 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 170 
                 pyrazol-1-yl 
                 CF3 
                 Cl 
                 2H-tetrazol-5-yl 
               
               
                 171 
                 pyrazol-1-yl 
                 CF3 
                 Cl 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 172 
                 pyrazol-1-yl 
                 CF3 
                 Br 
                 2H-tetrazol-5-yl 
               
               
                 173 
                 pyrazol-1-yl 
                 CF3 
                 Br 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 174 
                 phenyl 
                 CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 175 
                 phenyl 
                 CF2CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 176 
                 phenyl 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 177 
                 phenyl 
                 CF2CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 178 
                 phenyl 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 179 
                 phenyl 
                 CF2CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 180 
                 phenyl 
                 CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 181 
                 phenyl 
                 CF2CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 182 
                 phenyl 
                 CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 183 
                 phenyl 
                 CF2CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 184 
                 phenyl 
                 CF3 
                 I 
                 imidazol-1-yl 
                 179-180 
               
               
                 185 
                 phenyl 
                 CF2CF3 
                 I 
                 imidazol-1-yl 
               
               
                 186 
                 phenyl 
                 CF3 
                 F 
                 2H-tetrazol-5-yl 
               
               
                 187 
                 phenyl 
                 CF3 
                 F 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 188 
                 phenyl 
                 CF3 
                 Cl 
                 2H-tetrazol-5-yl 
               
               
                 189 
                 phenyl 
                 CF3 
                 Cl 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 190 
                 phenyl 
                 CF3 
                 Br 
                 2H-tetrazol-5-yl 
               
               
                 191 
                 phenyl 
                 CF3 
                 Br 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 192 
                 OCH3 
                 CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 193 
                 OCH3 
                 CF2CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 194 
                 OCH3 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 195 
                 OCH3 
                 CF2CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 196 
                 OCH3 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 197 
                 OCH3 
                 CF2CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 198 
                 OCH3 
                 CF3 
                 I 
                 3-(p-acetoxybenzylthio)-1,2,4-triazol-1-yl 
               
               
                 199 
                 OCH3 
                 CF3 
                 I 
                 3-amino-1,2,4-triazol-1-yl 
               
               
                 200 
                 OCH3 
                 CF3 
                 I 
                 3-bromo-1,2,4-triazol-1-yl 
               
               
                 201 
                 OCH3 
                 CF3 
                 I 
                 3-chloro-1,2,4-triazol-1-yl 
               
               
                 202 
                 OCH3 
                 CF3 
                 I 
                 3-cyano-1,2,4-triazol-1-yl 
               
               
                 203 
                 OCH3 
                 CF3 
                 I 
                 3-fluoro-1,2,4-triazol-1-yl 
               
               
                 204 
                 OCH3 
                 CF3 
                 I 
                 3-hydroxy-1,2,4-triazol-1-yl 
               
               
                 205 
                 OCH3 
                 CF3 
                 I 
                 3-mercapto-1,2,4-triazol-1-yl 
               
               
                 206 
                 OCH3 
                 CF3 
                 I 
                 3-methoxy-1,2,4-triazol-1-yl 
               
               
                 207 
                 OCH3 
                 CF3 
                 I 
                 3-methylamino-1,2,4-triazol-1-yl 
               
               
                 208 
                 OCH3 
                 CF3 
                 I 
                 3-methylthio-1,2,4-triazol-1-yl 
               
               
                 209 
                 OCH3 
                 CF3 
                 I 
                 3-trifluoromethyl-1,2,4-triazol-1-yl 
               
               
                 210 
                 OCH3 
                 CF3 
                 I 
                 5-(p-acetoxybenzylthio)imidazol-1-yl 
               
               
                 211 
                 OCH3 
                 CF3 
                 I 
                 5-(p-acetoxybenzylthio)-1,2,4-triazol-1-yl 
               
               
                 212 
                 OCH3 
                 CF3 
                 I 
                 4-aminoimidazol-1-yl 
               
               
                 213 
                 OCH3 
                 CF3 
                 I 
                 5-amino-1,2,4-triazol-1-yl 
               
               
                 214 
                 OCH3 
                 CF3 
                 I 
                 4-bromoimidazol-1-yl 
               
               
                 215 
                 OCH3 
                 CF3 
                 I 
                 5-bromo-1,2,4-triazol-1-yl 
               
               
                 216 
                 OCH3 
                 CF3 
                 I 
                 4-chloroimidazol-1-yl 
               
               
                 217 
                 OCH3 
                 CF3 
                 I 
                 5-chloro-1,2,4-triazol-1-yl 
               
               
                 218 
                 OCH3 
                 CF3 
                 I 
                 4-cyanoimidazol-1-yl 
               
               
                 219 
                 OCH3 
                 CF3 
                 I 
                 5-cyano-1,2,4-triazol-1-yl 
               
               
                 220 
                 OCH3 
                 CF3 
                 I 
                 4-fluoroimidazol-1-yl 
               
               
                 221 
                 OCH3 
                 CF3 
                 I 
                 5-fluoro-1,2,4-triazol-1-yl 
               
               
                 222 
                 OCH3 
                 CF3 
                 I 
                 4-hydroxyimidazol-1-yl 
               
               
                 223 
                 OCH3 
                 CF3 
                 I 
                 5-hydroxy-1,2,4-triazol-1-yl 
               
               
                 224 
                 OCH3 
                 CF3 
                 I 
                 4-mercaptoimidazol-1-yl 
               
               
                 225 
                 OCH3 
                 CF3 
                 I 
                 5-mercapto-1,2,4-triazol-1-yl 
               
               
                 226 
                 OCH3 
                 CF3 
                 I 
                 4-methoxyimidazol-1-yl 
               
               
                 227 
                 OCH3 
                 CF3 
                 I 
                 5-methoxy-1,2,4-triazol-1-yl 
               
               
                 228 
                 OCH3 
                 CF3 
                 I 
                 4-methylaminoimidazol-1-yl 
               
               
                 229 
                 OCH3 
                 CF3 
                 I 
                 5-methylamino-1,2,4-triazol-1-yl 
               
               
                 230 
                 OCH3 
                 CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 231 
                 OCH3 
                 CF2CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 232 
                 OCH3 
                 CF3 
                 I 
                 4-methylthioimidazol-1-yl 
               
               
                 233 
                 OCH3 
                 CF3 
                 I 
                 5-methylthio-1,2,4-triazol-1-yl 
               
               
                 234 
                 OCH3 
                 CF3 
                 I 
                 4-trifluoromethylimidazol-1-yl 
               
               
                 235 
                 OCH3 
                 CF3 
                 I 
                 5-trifluoromethyl-1,2,4-triazol-1-yl 
               
               
                 236 
                 OCH3 
                 CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 237 
                 OCH3 
                 CF2CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 238 
                 OCH3 
                 CF3 
                 I 
                 imidazol-1-yl 
                 111-113 
               
               
                 239 
                 OCH3 
                 CF2CF3 
                 I 
                 imidazol-1-yl 
               
               
                 240 
                 OCH3 
                 CF3 
                 F 
                 2H-tetrazol-5-yl 
               
               
                 241 
                 OCH3 
                 CF3 
                 F 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 242 
                 OCH3 
                 CF3 
                 Cl 
                 2H-tetrazol-5-yl 
               
               
                 243 
                 OCH3 
                 CF3 
                 Cl 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 244 
                 OCH3 
                 CF3 
                 Br 
                 2H-tetrazol-5-yl 
               
               
                 245 
                 OCH3 
                 CF3 
                 Br 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 246 
                 OCH2C°CH 
                 CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 247 
                 OCH2C°CH 
                 CF2CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 248 
                 OCH2C°CH 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 249 
                 OCH2C°CH 
                 CF2CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 250 
                 OCH2C°CH 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 251 
                 OCH2C°CH 
                 CF2CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 252 
                 OCH2C°CH 
                 CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 253 
                 OCH2C°CH 
                 CF2CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 254 
                 OCH2C°CH 
                 CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 255 
                 OCH2C°CH 
                 CF2CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 256 
                 OCH2C°CH 
                 CF3 
                 I 
                 imidazol-1-yl 
                 128-129 
               
               
                 257 
                 OCH2C°CH 
                 CF2CF3 
                 I 
                 imidazol-1-yl 
               
               
                 258 
                 OCH2C°CH 
                 CF3 
                 F 
                 2H-tetrazol-5-yl 
               
               
                 259 
                 OCH2C°CH 
                 CF3 
                 F 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 260 
                 OCH2C°CH 
                 CF3 
                 Cl 
                 2H-tetrazol-5-yl 
               
               
                 261 
                 OCH2C°CH 
                 CF3 
                 Cl 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 262 
                 OCH2C°CH 
                 CF3 
                 Br 
                 2H-tetrazol-5-yl 
               
               
                 263 
                 OCH2C°CH 
                 CF3 
                 Br 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 264 
                 OCH2CH3 
                 CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 265 
                 OCH2CH3 
                 CF2CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 266 
                 OCH2CH3 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 267 
                 OCH2CH3 
                 CF2CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 268 
                 OCH2CH3 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 269 
                 OCH2CH3 
                 CF2CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 270 
                 OCH2CH3 
                 CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 271 
                 OCH2CH3 
                 CF2CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 272 
                 OCH2CH3 
                 CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 273 
                 OCH2CH3 
                 CF2CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 274 
                 OCH2CH3 
                 CF3 
                 I 
                 imidazol-1-yl 
                 103-105 
               
               
                 275 
                 OCH2CH3 
                 CF2CF3 
                 I 
                 imidazol-1-yl 
               
               
                 276 
                 OCH2CH3 
                 CF3 
                 F 
                 2H-tetrazol-5-yl 
               
               
                 277 
                 OCH2CH3 
                 CF3 
                 F 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 278 
                 OCH2CH3 
                 CF3 
                 Cl 
                 2H-tetrazol-5-yl 
               
               
                 279 
                 OCH2CH3 
                 CF3 
                 Cl 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 280 
                 OCH2CH3 
                 CF3 
                 Br 
                 2H-tetrazol-5-yl 
               
               
                 281 
                 OCH2CH3 
                 CF3 
                 Br 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 282 
                 OCH2CH2CH3 
                 CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 283 
                 OCH2CH2CH3 
                 CF2CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 284 
                 OCH2CH2CH3 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 285 
                 OCH2CH2CH3 
                 CF2CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 286 
                 OCH2CH2CH3 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 287 
                 OCH2CH2CH3 
                 CF2CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 288 
                 OCH2CH2CH3 
                 CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 289 
                 OCH2CH2CH3 
                 CF2CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 290 
                 OCH2CH2CH3 
                 CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 291 
                 OCH2CH2CH3 
                 CF2CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 292 
                 OCH2CH2CH3 
                 CF3 
                 I 
                 imidazol-1-yl 
                 84-86 
               
               
                 293 
                 OCH2CH2CH3 
                 CF2CF3 
                 I 
                 imidazol-1-yl 
               
               
                 294 
                 OCH2CH2CH3 
                 CF3 
                 F 
                 2H-tetrazol-5-yl 
               
               
                 295 
                 OCH2CH2CH3 
                 CF3 
                 F 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 296 
                 OCH2CH2CH3 
                 CF3 
                 Cl 
                 2H-tetrazol-5-yl 
               
               
                 297 
                 OCH2CH2CH3 
                 CF3 
                 Cl 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 298 
                 OCH2CH2CH3 
                 CF3 
                 Br 
                 2H-tetrazol-5-yl 
               
               
                 299 
                 OCH2CH2CH3 
                 CF3 
                 Br 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 300 
                 OCH2CF2H 
                 CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 301 
                 OCH2CF2H 
                 CF2CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 302 
                 OCH2CF2H 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 303 
                 OCH2CF2H 
                 CF2CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 304 
                 OCH2CF2H 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 305 
                 OCH2CF2H 
                 CF2CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 306 
                 OCH2CF2H 
                 CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 307 
                 OCH2CF2H 
                 CF2CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 308 
                 OCH2CF2H 
                 CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 309 
                 OCH2CF2H 
                 CF2CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 310 
                 OCH2CF2H 
                 CF3 
                 I 
                 imidazol-1-yl 
                 97-98 
               
               
                 311 
                 OCH2CF2H 
                 CF2CF3 
                 I 
                 imidazol-1-yl 
               
               
                 312 
                 OCH2CF2H 
                 CF3 
                 F 
                 2H-tetrazol-5-yl 
               
               
                 313 
                 OCH2CF2H 
                 CF3 
                 F 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 314 
                 OCH2CF2H 
                 CF3 
                 Cl 
                 2H-tetrazol-5-yl 
               
               
                 315 
                 OCH2CF2H 
                 CF3 
                 Cl 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 316 
                 OCH2CF2H 
                 CF3 
                 Br 
                 2H-tetrazol-5-yl 
               
               
                 317 
                 OCH2CF2H 
                 CF3 
                 Br 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 318 
                 OCH(CH3)2 
                 CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 319 
                 OCH(CH3)2 
                 CF2CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 320 
                 OCH(CH3)2 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 321 
                 OCH(CH3)2 
                 CF2CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 322 
                 OCH(CH3)2 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 323 
                 OCH(CH3)2 
                 CF2CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 324 
                 OCH(CH3)2 
                 CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 325 
                 OCH(CH3)2 
                 CF2CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 326 
                 OCH(CH3)2 
                 CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 327 
                 OCH(CH3)2 
                 CF2CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 328 
                 OCH(CH3)2 
                 CF3 
                 I 
                 imidazol-1-yl 
                 97-98 
               
               
                 329 
                 OCH(CH3)2 
                 CF2CF3 
                 I 
                 imidazol-1-yl 
               
               
                 330 
                 OCH(CH3)2 
                 CF3 
                 F 
                 2H-tetrazol-5-yl 
               
               
                 331 
                 OCH(CH3)2 
                 CF3 
                 F 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 332 
                 OCH(CH3)2 
                 CF3 
                 Cl 
                 2H-tetrazol-5-yl 
               
               
                 333 
                 OCH(CH3)2 
                 CF3 
                 Cl 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 334 
                 OCH(CH3)2 
                 CF3 
                 Br 
                 2H-tetrazol-5-yl 
               
               
                 335 
                 OCH(CH3)2 
                 CF3 
                 Br 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 336 
                 imidazol-1-yl 
                 CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 337 
                 imidazol-1-yl 
                 CF2CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 338 
                 imidazol-1-yl 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 339 
                 imidazol-1-yl 
                 CF2CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 340 
                 imidazol-1-yl 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 341 
                 imidazol-1-yl 
                 CF2CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 342 
                 imidazol-1-yl 
                 CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 343 
                 imidazol-1-yl 
                 CF2CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 344 
                 imidazol-1-yl 
                 CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 345 
                 imidazol-1-yl 
                 CF2CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 346 
                 imidazol-1-yl 
                 CF3 
                 I 
                 imidazol-1-yl 
                 &gt;160   
               
               
                   
                   
                   
                   
                   
                 dec 
               
               
                 347 
                 imidazol-1-yl 
                 CF2CF3 
                 I 
                 imidazol-1-yl 
               
               
                 348 
                 imidazol-1-yl 
                 CF3 
                 F 
                 2H-tetrazol-5-yl 
               
               
                 349 
                 imidazol-1-yl 
                 CF3 
                 F 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 350 
                 imidazol-1-yl 
                 CF3 
                 F 
                 imidazol-1-yl 
                 142-150 
               
               
                   
                   
                   
                   
                   
                 dec 
               
               
                 351 
                 imidazol-1-yl 
                 CF3 
                 Cl 
                 2H-tetrazol-5-yl 
               
               
                 352 
                 imidazol-1-yl 
                 CF3 
                 Cl 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 353 
                 imidazol-1-yl 
                 CF3 
                 Br 
                 2H-tetrazol-5-yl 
               
               
                 354 
                 imidazol-1-yl 
                 CF3 
                 Br 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 355 
                 H 
                 CF3 
                 I 
                 1,2,4-triazol-1-yl 
                 115-116 
               
               
                 356 
                 H 
                 CF2CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 357 
                 H 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 358 
                 H 
                 CF2CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 359 
                 H 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 360 
                 H 
                 CF2CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 361 
                 H 
                 CF3 
                 I 
                 3-(p-acetoxybenzylthio)-1,2,4-triazol-1-yl 
               
               
                 362 
                 H 
                 CF3 
                 I 
                 3-amino-1,2,4-triazol-1-yl 
               
               
                 363 
                 H 
                 CF3 
                 I 
                 3-bromo-1,2,4-triazol-1-yl 
               
               
                 364 
                 H 
                 CF3 
                 I 
                 3-chloro-1,2,4-triazol-1-yl 
               
               
                 365 
                 H 
                 CF3 
                 I 
                 3-cyano-1,2,4-triazol-1-yl 
               
               
                 366 
                 H 
                 CF3 
                 I 
                 3-fluoro-1,2,4-triazol-1-yl 
               
               
                 367 
                 H 
                 CF3 
                 I 
                 3-hydroxy-1,2,4-triazol-1-yl 
               
               
                 368 
                 H 
                 CF3 
                 I 
                 3-mercapto-1,2,4-triazol-1-yl 
               
               
                 369 
                 H 
                 CF3 
                 I 
                 3-methoxy-1,2,4-triazol-1-yl 
               
               
                 370 
                 H 
                 CF3 
                 I 
                 3-methylamino-1,2,4-triazol-1-yl 
               
               
                 371 
                 H 
                 CF3 
                 I 
                 3-methylthio-1,2,4-triazol-1-yl 
               
               
                 372 
                 H 
                 CF3 
                 I 
                 3-trifluoromethyl-1,2,4-triazol-1-yl 
               
               
                 373 
                 H 
                 CF3 
                 I 
                 5-(p-acetoxybenzylthio)imidazol-1-yl 
               
               
                 374 
                 H 
                 CF3 
                 I 
                 5-(p-acetoxybenzylthio)-1,2,4-triazol-1-yl 
               
               
                 375 
                 H 
                 CF3 
                 I 
                 4-aminoimidazol-1-yl 
               
               
                 376 
                 H 
                 CF3 
                 I 
                 5-amino-1,2,4-triazol-1-yl 
               
               
                 377 
                 H 
                 CF3 
                 I 
                 4-bromoimidazol-1-yl 
               
               
                 378 
                 H 
                 CF3 
                 I 
                 5-bromo-1,2,4-triazol-1-yl 
               
               
                 379 
                 H 
                 CF3 
                 I 
                 4-chloroimidazol-1-yl 
               
               
                 380 
                 H 
                 CF3 
                 I 
                 5-chloro-1,2,4-triazol-1-yl 
               
               
                 381 
                 H 
                 CF3 
                 I 
                 4-cyanoimidazol-1-yl 
               
               
                 382 
                 H 
                 CF3 
                 I 
                 5-cyano-1,2,4-triazol-1-yl 
               
               
                 383 
                 H 
                 CF3 
                 I 
                 4-fluoroimidazol-1-yl 
               
               
                 384 
                 H 
                 CF3 
                 I 
                 5-fluoro-1,2,4-triazol-1-yl 
               
               
                 385 
                 H 
                 CF3 
                 I 
                 4-hydroxyimidazol-1-yl 
               
               
                 386 
                 H 
                 CF3 
                 I 
                 5-hydroxy-1,2,4-triazol-1-yl 
               
               
                 387 
                 H 
                 CF3 
                 I 
                 4-mercaptoimidazol-1-yl 
               
               
                 388 
                 H 
                 CF3 
                 I 
                 5-mercapto-1,2,4-triazol-1-yl 
               
               
                 389 
                 H 
                 CF3 
                 I 
                 4-methoxyimidazol-1-yl 
               
               
                 390 
                 H 
                 CF3 
                 I 
                 5-methoxy-1,2,4-triazol-1-yl 
               
               
                 391 
                 H 
                 CF3 
                 I 
                 4-methylaminoimidazol-1-yl 
               
               
                 392 
                 H 
                 CF3 
                 I 
                 5-methylamino-1,2,4-triazol-1-yl 
               
               
                 393 
                 H 
                 CF3 
                 I 
                 4-methylimidazol-1-yl 
                 173-175 
               
               
                 394 
                 H 
                 CF2CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 395 
                 H 
                 CF3 
                 I 
                 4-methylthioimidazol-1-yl 
               
               
                 396 
                 H 
                 CF3 
                 I 
                 5-methylthio-1,2,4-triazol-1-yl 
               
               
                 397 
                 H 
                 CF3 
                 I 
                 4-trifluoromethylimidazol-1-yl 
               
               
                 398 
                 H 
                 CF3 
                 I 
                 5-trifluoromethyl-1,2,4-triazol-1-yl 
               
               
                 399 
                 H 
                 CF3 
                 I 
                 benzimidazol-1-yl 
                 119-120 
               
               
                 400 
                 H 
                 CF2CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 401 
                 H 
                 CF3 
                 I 
                 imidazol-1-yl 
                 108-109 
               
               
                 402 
                 H 
                 CF2CF3 
                 I 
                 imidazol-1-yl 
               
               
                 403 
                 H 
                 CF3 
                 F 
                 2H-tetrazol-5-yl 
               
               
                 404 
                 H 
                 CF3 
                 F 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 405 
                 H 
                 CF3 
                 Cl 
                 2H-tetrazol-5-yl 
               
               
                 406 
                 H 
                 CF3 
                 Cl 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 407 
                 H 
                 CF3 
                 Br 
                 2H-tetrazol-5-yl 
               
               
                 408 
                 H 
                 CF3 
                 Br 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 409 
                 C°CSi(CH3)3 
                 CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 410 
                 C°CSi(CH3)3 
                 CF2CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 411 
                 C°CSi(CH3)3 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 412 
                 C°CSi(CH3)3 
                 CF2CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 413 
                 C°CSi(CH3)3 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 414 
                 C°CSi(CH3)3 
                 CF2CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 415 
                 C°CSi(CH3)3 
                 CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 416 
                 C°CSi(CH3)3 
                 CF2CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 417 
                 C°CSi(CH3)3 
                 CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 418 
                 C°CSi(CH3)3 
                 CF2CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 419 
                 C°CSi(CH3)3 
                 CF3 
                 I 
                 imidazol-1-yl 
                 oil 
               
               
                 420 
                 C°CSi(CH3)3 
                 CF2CF3 
                 I 
                 imidazol-1-yl 
               
               
                 421 
                 C°CSi(CH3)3 
                 CF3 
                 F 
                 2H-tetrazol-5-yl 
               
               
                 422 
                 C°CSi(CH3)3 
                 CF3 
                 F 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 423 
                 C°CSi(CH3)3 
                 CF3 
                 Cl 
                 2H-tetrazol-5-yl 
               
               
                 424 
                 C°CSi(CH3)3 
                 CF3 
                 Cl 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 425 
                 C°CSi(CH3)3 
                 CF3 
                 Br 
                 2H-tetrazol-5-yl 
               
               
                 426 
                 C°CSi(CH3)3 
                 CF3 
                 Br 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 427 
                 CH3 
                 CF3 
                 vinyl 
                 imidazol-1-yl 
                 oil 
               
               
                 428 
                 CH3 
                 CF3 
                 I 
                 1,2,4-triazol-1-yl 
                 119-121 
               
               
                 429 
                 CH3 
                 CF2CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 430 
                 CH3 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
                 180-182 
               
               
                 431 
                 CH3 
                 CF2CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 432 
                 CH3 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
                 131-133 
               
               
                 433 
                 CH3 
                 CF2CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 434 
                 CH3 
                 CF3 
                 I 
                 3-(p-acetoxybenzylthio)-1,2,4-triazol-1-yl 
               
               
                 435 
                 CH3 
                 CF3 
                 I 
                 3-amino-1,2,4-triazol-1-yl 
               
               
                 436 
                 CH3 
                 CF3 
                 I 
                 3-bromo-1,2,4-triazol-1-yl 
               
               
                 437 
                 CH3 
                 CF3 
                 I 
                 3-chloro-1,2,4-triazol-1-yl 
               
               
                 438 
                 CH3 
                 CF3 
                 I 
                 3-cyano-1,2,4-triazol-1-yl 
               
               
                 439 
                 CH3 
                 CF3 
                 I 
                 3-fluoro-1,2,4-triazol-1-yl 
               
               
                 440 
                 CH3 
                 CF3 
                 I 
                 3-hydroxy-1,2,4-triazol-1-yl 
               
               
                 441 
                 CH3 
                 CF3 
                 I 
                 3-mercapto-1,2,4-triazol-1-yl 
               
               
                 442 
                 CH3 
                 CF3 
                 I 
                 3-methoxy-1,2,4-triazol-1-yl 
               
               
                 443 
                 CH3 
                 CF3 
                 I 
                 3-methylamino-1,2,4-triazol-1-yl 
               
               
                 444 
                 CH3 
                 CF3 
                 I 
                 3-methylthio-1,2,4-triazol-1-yl 
               
               
                 445 
                 CH3 
                 CF3 
                 I 
                 3-trifluoromethyl-1,2,4-triazol-1-yl 
               
               
                 446 
                 CH3 
                 CF3 
                 I 
                 5-(p-acetoxybenzylthio)imidazol-1-yl 
               
               
                 447 
                 CH3 
                 CF3 
                 I 
                 5-(p-acetoxybenzylthio)-1,2,4-triazol-1-yl 
               
               
                 448 
                 CH3 
                 CF3 
                 I 
                 4-aminoimidazol-1-yl 
               
               
                 449 
                 CH3 
                 CF3 
                 I 
                 5-amino-1,2,4-triazol-1-yl 
               
               
                 450 
                 CH3 
                 CF3 
                 I 
                 4-bromoimidazol-1-yl 
               
               
                 451 
                 CH3 
                 CF3 
                 I 
                 5-bromo-1,2,4-triazol-1-yl 
               
               
                 452 
                 CH3 
                 CF3 
                 I 
                 4-chloroimidazol-1-yl 
               
               
                 453 
                 CH3 
                 CF3 
                 I 
                 5-chloro-1,2,4-triazol-1-yl 
               
               
                 454 
                 CH3 
                 CF3 
                 I 
                 4-cyanoimidazol-1-yl 
               
               
                 455 
                 CH3 
                 CF3 
                 I 
                 5-cyano-1,2,4-triazol-1-yl 
               
               
                 456 
                 CH3 
                 CF3 
                 I 
                 4-fluoroimidazol-1-yl 
               
               
                 457 
                 CH3 
                 CF3 
                 I 
                 5-fluoro-1,2,4-triazol-1-yl 
               
               
                 458 
                 CH3 
                 CF3 
                 I 
                 4-hydroxyimidazol-1-yl 
               
               
                 459 
                 CH3 
                 CF3 
                 I 
                 5-hydroxy-1,2,4-triazol-1-yl 
               
               
                 460 
                 CH3 
                 CF3 
                 I 
                 4-mercaptoimidazol-1-yl 
               
               
                 461 
                 CH3 
                 CF3 
                 I 
                 5-mercapto-1,2,4-triazol-1-yl 
               
               
                 462 
                 CH3 
                 CF3 
                 I 
                 4-methoxyimidazol-1-yl 
               
               
                 463 
                 CH3 
                 CF3 
                 I 
                 5-methoxy-1,2,4-triazol-1-yl 
               
               
                 464 
                 CH3 
                 CF3 
                 I 
                 4-methylaminoimidazol-1-yl 
               
               
                 465 
                 CH3 
                 CF3 
                 I 
                 5-methylamino-1,2,4-triazol-1-yl 
               
               
                 466 
                 CH3 
                 CF3 
                 I 
                 4-methylimidazol-1-yl 
                 155-156 
               
               
                 467 
                 CH3 
                 CF2CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 468 
                 CH3 
                 CF3 
                 I 
                 4-methylthioimidazol-1-yl 
               
               
                 469 
                 CH3 
                 CF3 
                 I 
                 5-methylthio-1,2,4-triazol-1-yl 
               
               
                 470 
                 CH3 
                 CF3 
                 I 
                 4-trifluoromethylimidazol-1-yl 
               
               
                 471 
                 CH3 
                 CF3 
                 I 
                 5-trifluoromethyl-1,2,4-triazol-1-yl 
               
               
                 472 
                 CH3 
                 CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 473 
                 CH3 
                 CF2CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 474 
                 CH3 
                 CF3 
                 I 
                 imidazol-1-yl 
                 145-148 
               
               
                 475 
                 CH3 
                 CF2CF3 
                 I 
                 imidazol-1-yl 
               
               
                 476 
                 CH3 
                 CF3 
                 F 
                 2H-tetrazol-5-yl 
               
               
                 477 
                 CH3 
                 CF3 
                 F 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 478 
                 CH3 
                 CF3 
                 ethynyl 
                 imidazol-1-yl 
                 121-122 
               
               
                 479 
                 CH3 
                 CF3 
                 Cl 
                 2H-tetrazol-5-yl 
               
               
                 480 
                 CH3 
                 CF3 
                 Cl 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 481 
                 CH3 
                 CF3 
                 Br 
                 2H-tetrazol-5-yl 
               
               
                 482 
                 CH3 
                 CF3 
                 Br 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 483 
                 CH3 
                 CF3 
                 Br 
                 imidazol-1-yl 
                 72-73 
               
               
                 484 
                 CH3 
                 CF3 
                 1-chloro- 
                 imidazol-1-yl 
                 oil 
               
               
                   
                   
                   
                 vinyl 
               
               
                 485 
                 CH2CH3 
                 CF3 
                 I 
                 1,2,4-triazol-1-yl 
                 50-51 
               
               
                 486 
                 CH2CH3 
                 CF2CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 487 
                 CH2CH3 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 488 
                 CH2CH3 
                 CF2CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 489 
                 CH2CH3 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 490 
                 CR2CH3 
                 CF2CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 491 
                 CH2CH3 
                 CF3 
                 I 
                 3-(p-acetoxybenzylthio)-1,2,4-triazol-1-yl 
               
               
                 492 
                 CH2CH3 
                 CF3 
                 I 
                 3-amino-1,2,4-triazol-1-yl 
               
               
                 493 
                 CH2CH3 
                 CF3 
                 I 
                 3-bromo-1,2,4-triazol-1-yl 
               
               
                 494 
                 CH2CH3 
                 CF3 
                 I 
                 3-chloro-1,2,4-triazol-1-yl 
               
               
                 495 
                 CH2CH3 
                 CF3 
                 I 
                 3-cyano-1,2,4-triazol-1-yl 
               
               
                 496 
                 CH2CH3 
                 CF3 
                 I 
                 3-fluoro-1,2,4-triazol-1-yl 
               
               
                 497 
                 CH2CH3 
                 CF3 
                 I 
                 3-hydroxy-1,2,4-triazol-1-yl 
               
               
                 498 
                 CH2CH3 
                 CF3 
                 I 
                 3-mercapto-1,2,4-triazol-1-yl 
               
               
                 499 
                 CH2CH3 
                 CF3 
                 I 
                 3-methoxy-1,2,4-triazol-1-yl 
               
               
                 500 
                 CH2CH3 
                 CF3 
                 I 
                 3-methylamino-1,2,4-triazol-1-yl 
               
               
                 501 
                 CH2CH3 
                 CF3 
                 I 
                 3-methylthio-1,2,4-triazol-1-yl 
               
               
                 502 
                 CH2CH3 
                 CF3 
                 I 
                 3-trifluoromethyl-1,2,4-triazol-1-yl 
               
               
                 503 
                 CH2CH3 
                 CF3 
                 I 
                 5-(p-acetoxybenzylthio)imidazol-1-yl 
               
               
                 504 
                 CH2CH3 
                 CF3 
                 I 
                 5-(p-acetoxybenzylthio)-1,2,4-triazol-1-yl 
               
               
                 505 
                 CH2CH3 
                 CF3 
                 I 
                 4-aminoimidazol-1-yl 
               
               
                 506 
                 CH2CH3 
                 CF3 
                 I 
                 5-amino-1,2,4-triazol-1-yl 
               
               
                 507 
                 CH2CH3 
                 CF3 
                 I 
                 4-bromoimidazol-1-yl 
               
               
                 508 
                 CH2CH3 
                 CF3 
                 I 
                 5-bromo-1,2,4-triazol-1-yl 
               
               
                 509 
                 CH2CH3 
                 CF3 
                 I 
                 4-chloroimidazol-1-yl 
               
               
                 510 
                 CH2CH3 
                 CF3 
                 I 
                 5-chloro-1,2,4-triazol-1-yl 
               
               
                 511 
                 CH2CH3 
                 CF3 
                 I 
                 4-cyanoimidazol-1-yl 
               
               
                 512 
                 CH2CH3 
                 CF3 
                 I 
                 5-cyano-1,2,4-triazol-1-yl 
               
               
                 513 
                 CH2CH3 
                 CF3 
                 I 
                 4-fluoroimidazol-1-yl 
               
               
                 514 
                 CH2CH3 
                 CF3 
                 I 
                 5-fluoro-1,2,4-triazol-1-yl 
               
               
                 515 
                 CH2CH3 
                 CF3 
                 I 
                 4-hydroxyimidazol-1-yl 
               
               
                 516 
                 CH2CH3 
                 CF3 
                 I 
                 5-hydroxy-1,2,4-triazol-1-yl 
               
               
                 517 
                 CH2CH3 
                 CF3 
                 I 
                 4-mercaptoimidazol-1-yl 
               
               
                 518 
                 CH2CH3 
                 CF3 
                 I 
                 5-mercapto-1,2,4-triazol-1-yl 
               
               
                 519 
                 CH2CH3 
                 CF3 
                 I 
                 4-methoxyimidazol-1-yl 
               
               
                 520 
                 CH2CH3 
                 CF3 
                 I 
                 5-methoxy-1,2,4-triazol-1-yl 
               
               
                 521 
                 CH2CH3 
                 CF3 
                 I 
                 4-methylaminoimidazol-1-yl 
               
               
                 522 
                 CH2CH3 
                 CF3 
                 I 
                 5-methylamino-1,2,4-triazol-1-yl 
               
               
                 523 
                 CH2CH3 
                 CF3 
                 I 
                 4-methylimidazol-1-yl 
                 110-111 
               
               
                 524 
                 CH2CH3 
                 CF2CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 525 
                 CH2CH3 
                 CF3 
                 I 
                 4-methylthioimidazol-1-yl 
               
               
                 526 
                 CH2CH3 
                 CF3 
                 I 
                 5-methylthio-1,2,4-triazol-1-yl 
               
               
                 527 
                 CH2CH3 
                 CF3 
                 I 
                 4-trifluoromethylimidazol-1-yl 
               
               
                 528 
                 CH2CH3 
                 CF3 
                 I 
                 5-trifluoromethyl-1,2,4-triazol-1-yl 
               
               
                 529 
                 CH2CH3 
                 CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 530 
                 CH2CH3 
                 CF2CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 531 
                 CH2CH3 
                 CF3 
                 I 
                 imidazol-1-yl 
                 124 
               
               
                 532 
                 CH2CH3 
                 CF2CF3 
                 I 
                 imidazol-1-yl 
               
               
                 533 
                 CH2CH3 
                 CF3 
                 F 
                 2H-tetrazol-5-yl 
               
               
                 534 
                 CH2CH3 
                 CF3 
                 F 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 535 
                 CH2CH3 
                 CF3 
                 Cl 
                 2H-tetrazol-5-yl 
               
               
                 536 
                 CH2CH3 
                 CF3 
                 Cl 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 537 
                 CH2CH3 
                 CF3 
                 Br 
                 2H-tetrazol-5-yl 
               
               
                 538 
                 CH2CH3 
                 CF3 
                 Br 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 539 
                 6-phenylpiridin-2-yl 
                 CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 540 
                 6-phenylpiridin-2-yl 
                 CF2CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 541 
                 6-phenylpiridin-2-yl 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 542 
                 6-phenylpiridin-2-yl 
                 CF2CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 543 
                 6-phenylpiridin-2-yl 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 544 
                 6-phenylpiridin-2-yl 
                 CF2CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 545 
                 6-phenylpiridin-2-yl 
                 CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 546 
                 6-phenylpiridin-2-yl 
                 CF2CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 547 
                 6-phenylpiridin-2-yl 
                 CF3 
                 I 
                 benzimidzol-1-yl 
               
               
                 548 
                 6-phenylpiridin-2-yl 
                 CF2CF3 
                 I 
                 benzimidzol-1-yl 
               
               
                 549 
                 6-phenylpiridin-2-yl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 550 
                 6-phenylpiridin-2-yl 
                 CF2CF3 
                 I 
                 imidazol-1-yl 
               
               
                 551 
                 6-phenylpiridin-2-yl 
                 CF3 
                 F 
                 2H-tetrazol-5-yl 
               
               
                 552 
                 6-phenylpiridin-2-yl 
                 CF3 
                 F 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 553 
                 6-phenylpiridin-2-yl 
                 CF3 
                 Cl 
                 2H-tetrazol-5-yl 
               
               
                 554 
                 6-phenylpiridin-2-yl 
                 CF3 
                 Cl 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 555 
                 6-phenylpiridin-2-yl 
                 CF3 
                 Br 
                 2H-tetrazol-5-yl 
               
               
                 556 
                 6-phenylpiridin-2-yl 
                 CF3 
                 Br 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 557 
                 6-phenylpiridin-2-yl 
                 CF3 
                 Br 
                 imidazol-1-yl 
                 136-138 
               
               
                 558 
                 6-methylpiridin-2-yl 
                 CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 559 
                 6-methylpiridin-2-yl 
                 CF2CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 560 
                 6-methylpiridin-2-yl 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 561 
                 6-methylpiridin-2-yl 
                 CF2CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 562 
                 6-methylpiridin-2-yl 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 563 
                 6-methylpiridin-2-yl 
                 CF2CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 564 
                 6-methylpiridin-2-yl 
                 CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 565 
                 6-methylpiridin-2-yl 
                 CF2CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 566 
                 6-methylpiridin-2-yl 
                 CF3 
                 I 
                 benzimidzol-1-yl 
               
               
                 567 
                 6-methylpiridin-2-yl 
                 CF2CF3 
                 I 
                 benzimidzol-1-yl 
               
               
                 568 
                 6-methylpiridin-2-yl 
                 CF3 
                 I 
                 imidazol-1-yl 
                 141-143 
               
               
                 569 
                 6-methylpiridin-2-yl 
                 CF2CF3 
                 I 
                 imidazol-1-yl 
               
               
                 570 
                 6-methylpiridin-2-yl 
                 CF3 
                 F 
                 2H-tetrazol-5-yl 
               
               
                 571 
                 6-methylpiridin-2-yl 
                 CF3 
                 F 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 572 
                 6-methylpiridin-2-yl 
                 CF3 
                 Cl 
                 2H-tetrazol-5-yl 
               
               
                 573 
                 6-methylpiridin-2-yl 
                 CF3 
                 Cl 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 574 
                 6-methylpiridin-2-yl 
                 CF3 
                 Br 
                 2H-tetrazol-5-yl 
               
               
                 575 
                 6-methylpiridin-2-yl 
                 CF3 
                 Br 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 576 
                 2-oxopyrrolidin-1-yl 
                 CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 577 
                 2-oxopyrrolidin-1-yl 
                 CF2CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 578 
                 2-oxopyrrolidin-1-yl 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 579 
                 2-oxopyrrolidin-1-yl 
                 CF2CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 580 
                 2-oxopyrrolidin-1-yl 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 581 
                 2-oxopyrrolidin-1-yl 
                 CF2CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 582 
                 2-oxopyrrolidin-1-yl 
                 CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 583 
                 2-oxopyrrolidin-1-yl 
                 CF2CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 584 
                 2-oxopyrrolidin-1-yl 
                 CF3 
                 I 
                 benzimidzol-1-yl 
               
               
                 585 
                 2-oxopyrrolidin-1-yl 
                 CF2CF3 
                 I 
                 benzimidzol-1-yl 
               
               
                 586 
                 2-oxopyrrolidin-1-yl 
                 CF3 
                 I 
                 imidazol-1-yl 
                 195-197 
               
               
                 587 
                 2-oxopyrrolidin-1-yl 
                 CF2CF3 
                 I 
                 imidazol-1-yl 
               
               
                 588 
                 2-oxopyrrolidin-1-yl 
                 CF3 
                 F 
                 2H-tetrazol-5-yl 
               
               
                 589 
                 2-oxopyrrolidin-1-yl 
                 CF3 
                 F 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 590 
                 2-oxopyrrolidin-1-yl 
                 CF3 
                 Cl 
                 2H-tetrazol-5-yl 
               
               
                 591 
                 2-oxopyrrolidin-1-yl 
                 CF3 
                 Cl 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 592 
                 2-oxopyrrolidin-1-yl 
                 CF3 
                 Br 
                 2H-tetrazol-5-yl 
               
               
                 593 
                 2-oxopyrrolidin-1-yl 
                 CF3 
                 Br 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 594 
                 CH3 
                 CF3 
                 I 
                 1-methyl-1H-tetrazol-5-yl 
                 110-112 
               
               
                 595 
                 SCH3 
                 CF3 
                 I 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 596 
                 SCH2CH3 
                 CF3 
                 I 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 597 
                 OCH3 
                 CF3 
                 I 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 598 
                 OCH2CH3 
                 CF3 
                 I 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 599 
                 H 
                 CF3 
                 I 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 600 
                 CH2CH3 
                 CF3 
                 I 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 601 
                 phenyl 
                 CF3 
                 I 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 602 
                 imidazol-1-yl 
                 CF3 
                 I 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 603 
                 pyridin-2-yl 
                 CF3 
                 I 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 604 
                 pyridin-3-yl 
                 CF3 
                 I 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 605 
                 pyridin-4-yl 
                 CF3 
                 I 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 606 
                 CH3 
                 CF3 
                 Br 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 607 
                 SCH3 
                 CF3 
                 Br 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 608 
                 SCH2CH3 
                 CF3 
                 Br 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 609 
                 OCH3 
                 CF3 
                 Br 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 610 
                 OCH2CH3 
                 CF3 
                 Br 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 611 
                 H 
                 CF3 
                 Br 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 612 
                 CH2CH3 
                 CF3 
                 Br 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 613 
                 phenyl 
                 CF3 
                 Br 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 614 
                 imidazol-1-yl 
                 CF3 
                 Br 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 615 
                 pyridin-2-yl 
                 CF3 
                 Br 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 616 
                 pyridin-3-yl 
                 CF3 
                 Br 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 617 
                 pyridin-4-yl 
                 CF3 
                 Br 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 618 
                 CH3 
                 CF3 
                 Cl 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 619 
                 SCH3 
                 CF3 
                 Cl 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 620 
                 SCH2CH3 
                 CF3 
                 Cl 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 621 
                 OCH3 
                 CF3 
                 Cl 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 622 
                 OCH2CH3 
                 CF3 
                 Cl 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 623 
                 H 
                 CF3 
                 Cl 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 624 
                 CH2CH3 
                 CF3 
                 Cl 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 625 
                 phenyl 
                 CF3 
                 Cl 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 626 
                 imidazol-1-yl 
                 CF3 
                 Cl 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 627 
                 pyridin-2-yl 
                 CF3 
                 Cl 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 628 
                 pyridin-3-yl 
                 CF3 
                 Cl 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 629 
                 pyridin-4-yl 
                 CF3 
                 Cl 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 630 
                 CH3 
                 CF3 
                 F 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 631 
                 SCH3 
                 CF3 
                 F 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 632 
                 SCH2CH3 
                 CF3 
                 F 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 633 
                 OCH3 
                 CF3 
                 F 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 634 
                 OCH2CH3 
                 CF3 
                 F 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 635 
                 H 
                 CF3 
                 F 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 636 
                 CH2CH3 
                 CF3 
                 F 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 637 
                 phenyl 
                 CF3 
                 F 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 638 
                 imidazol-1-yl 
                 CF3 
                 F 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 639 
                 pyridin-2-yl 
                 CF3 
                 F 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 640 
                 pyridin-3-yl 
                 CF3 
                 F 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 641 
                 pyridin-4-yl 
                 CF3 
                 F 
                 1-methyl-1H-tetrazol-5-yl 
               
               
                 642 
                 SCH2F 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 643 
                 SCH2Cl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 644 
                 SCF3 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 645 
                 S(O)CH3 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 646 
                 S(O)CF3 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 647 
                 S(O)2CF3 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 648 
                 6-phenylpyridin-4-yl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 649 
                 6-phenylpyridin-4-yl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 650 
                 6-chloropyridin-4-yl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 651 
                 5- 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                   
                 trifluoromethylpyridin- 
               
               
                   
                 4-yl 
               
               
                 652 
                 6-phenylpyridin-3-yl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 653 
                 6-methylpyridin-3-yl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 654 
                 6-chloropyridin-3-yl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 655 
                 6- 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                   
                 trifluoromethylpyridin- 
               
               
                   
                 3-yl 
               
               
                 656 
                 pyridin-3-yl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 657 
                 6-chloropyridin-2-yl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 658 
                 6- 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                   
                 trifluoromethylpyridin- 
               
               
                   
                 2-yl 
               
               
                 659 
                 3-methylpyrazol-1-yl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 660 
                 3-methoxypyrazol-1-yl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 661 
                 3-chloropyrazol-1-yl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 662 
                 2-tolyl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 663 
                 3-tolyl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 664 
                 4-tolyl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 665 
                 2-chlorophenyl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 666 
                 3-chlorophenyl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 667 
                 4-chlorophenyl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 668 
                 2-methoxyphenyl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 669 
                 3-methoxyphenyl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 670 
                 4-methoxyphenyl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 671 
                 2- 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                   
                 (trifluoromethyl)phenyl 
               
               
                 672 
                 3- 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                   
                 (trifluoromethyl)phenyl 
               
               
                 673 
                 4- 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                   
                 (trifluoromethyl)phenyl 
               
               
                 674 
                 OCH2CF3 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 675 
                 OCH2C°CCH2Cl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 676 
                 OCH═CHCF3 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 677 
                 4-methylimidazol-1-yl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 678 
                 4-methoxyimidazol-1- 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                   
                 yl 
               
               
                 679 
                 4-chloroimidazol-1-yl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 680 
                 C°CCH2Cl 
                 CF3 
                 I 
                 imidazol-1-yl 
               
               
                 681 
                 CF3 
                 CF3 
                 I 
                 1,2,4-triazol-1-yl 
                 137-138 
               
               
                 682 
                 CF3 
                 CF2CF3 
                 I 
                 1,2,4-triazol-1-yl 
               
               
                 683 
                 CF3 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 684 
                 CF3 
                 CF2CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 685 
                 CF3 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 686 
                 CF3 
                 CF2CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 687 
                 CF3 
                 CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 688 
                 CF3 
                 CF2CF3 
                 I 
                 4-methylimidazol-1-yl 
               
               
                 689 
                 CF3 
                 CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 690 
                 CF3 
                 CF2CF3 
                 I 
                 benzimidazol-1-yl 
               
               
                 691 
                 CF3 
                 CF2CF3 
                 I 
                 imidazol-1-yl 
               
               
                 692 
                 CF3 
                 CF3 
                 I 
                 imidazol-1-yl 
                 105-106 
               
               
                 693 
                 CF3 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 694 
                 CF3 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 695 
                 CF3 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 696 
                 CF3 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 697 
                 CF3 
                 CF3 
                 I 
                 2H-tetrazol-5-yl 
               
               
                 698 
                 CF3 
                 CF3 
                 I 
                 2-methyl-2H-tetrazol-5-yl 
               
               
                 699 
                 CH═CHCH2Cl 
                 CF3 
                 I 
                 imidazol-1-yl