Fungicidal pyrimidine derivatives

Abstract

Fungicidal pyrimidine derivatives and the use as a fungicide of the compounds of formula (1): wherein R1 is H, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C1-C6alkoxy, C3-C6cycloalkoxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, phenyl, pyridinyl or azolyl groups, (being optionally substituted by one or more substituents); or N(R4)C(O)R5, R2 is polyfluoroalkyl, R3 is fluorine, chlorine, bromine or iodine; ethenyl or ethynyl (being optionally substituted by one or more of halogen), R4 and R5 are, independently, H, C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl groups, (being optionally substituted by one or more of halogen or cyano); or R4 and R5 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 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 2002-067684 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

R¹ is H, C₁-C₆alkyl (being optionally substituted by one or more of halogen), C₂-C₆alkenyl (being optionally substituted by one or more of halogen), C₂-C₆alkynyl (being optionally substituted by one or more of halogen or trialkylsilyl), C₁-C₆alkoxy (being optionally substituted by one or more of halogen), C₂-C₆alkenyloxy (being optionally substituted by one or more of halogen), C₂-C₆alkynyloxy (being optionally substituted by one or more of halogen), C₁-C₆alkylthio (being optionally substituted by one or more of halogen), C₁-C₆alkylsulfinyl (being optionally substituted by one or more of halogen), C₁-C₆alkylsulfonyl (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(R⁴)C(O)R⁵,

• R² is haloC₁-C₆alkyl,
• R³ is halogen, C₂-C₆alkenyl or C₂-C₆alkynyl groups, (being optionally substituted by one or more of halogen),
• R⁴ and R⁵ are, independently, H, C₁-C₆alkyl (being optionally substituted by one or more of halogen or cyano); or R⁴ and R⁵ 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 R¹ is H, C₁-C₆alkyl (being optionally substituted by one or more of halogen), C₂-C₆alkenyl (being optionally substituted by one or more of halogen), C₂-C₆alkynyl (being optionally substituted by one or more of halogen or trialkylsilyl), C₂-C₆alkoxy (being optionally substituted by one or more of halogen), C₂-C₆alkenyloxy (being optionally substituted by one or more of halogen), C₂-C₆alkynyloxy (being optionally substituted by one or more of halogen), C₁-C₆alkylthio (being optionally substituted by one or more of halogen), C₁-C₆alkylsulfinyl (being optionally substituted by one or more of halogen), C₁-C₆alkylsulfonyl (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(R⁴)C(O)R⁵,

• R² is haloC₁-C₆alkyl, R³ is halogen, C₂-C₆alkenyl or C₂-C₆alkynyl groups, (being optionally substituted by one or more of halogen), R⁴ and R⁵ are, independently, H, C₁-C₆alkyl (being optionally substituted by one or more of halogen or cyano); or R⁴ and R⁵ 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).

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 4-chloropyrimidines (wherein R¹═H, alkyl, phenyl, pyridine-2-yl, pyridine-3-yl or pyridine-4-yl) such as 1-4 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 R³═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.

SCHEME 5

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-alkylsulfonyl-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 4-methoxypyrimidine 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-halogeno-4-methoxypyrimidine 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-alkenyl-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 tetrahydrofuran, 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 nuda)
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 kaki)
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 mlold                 (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 susceptible-strains of pathogenic fungi but also to the resistant-strains of pathogenic fungi to benzimidazole 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'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, tolclofos-methyl, pyrazophos, fosetyl-Al, etc.

Benzimidazole Fungicides

Thiophanate-methyl, benomyl, carbendazim, thiabendazole, etc.

Dicarboxyimide Fungicides

Oxycarboxine, mepronyl, flutolanil, techlofthalam, trichlamide, 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, diethofencarb, binapacryl, lecithin, sodium hydrogencarbonate, fenaminosulf, dodine, dimethomorph, 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, amitraz, 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 A₃, Gibberelline A₄, Gibberelline A₇, 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-6-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 for 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 sulfate 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 DMF (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-methyl-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 temperature. 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 (hexane-ethyl 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) THF (5 ml) solution at once and the temperature was raised up to room temperature and then added water. The reaction mixture was 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 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 gel column chromatography (hexane-ethyl acetate) to give 4-cyano-5-iodo-2-methylthio-6-trifluoromethylpyrimidine (2.56 g) as yellow solid, mp 68-69° C.

Example 11

4-Imidazol-1-yl-5-iodo-2-isopropylthio-6-trifluoromethyl-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 for 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 recrystallized from methanol-water mixture as colorless needles (2.61 g), mp 118-120° C.

Example 12

Ethyl 1-(5-iodo-2-isopropylthio-6-trifluoromethylpyrimidin-4-yl)-3-trifluoromethyl-1H-pyrazole-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]-undec-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 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) 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)-6-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)-6-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. ¹H-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.; 23, 25, 39, 47, 48, 54, 68, 78, 86, 90, 128, 145, 238, 256, 274, 292, 328, 346, 377, 379, 393, 399, 401, 474, 531, 568, 586, 700, 722, 724, 1026, 1028, 1032

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 for 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 fungus (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 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.; 23, 25, 39, 47, 48, 54, 68, 90, 184, 238, 256, 274, 292, 355, 356, 359, 377, 379, 393, 399, 402, 432, 485, 489, 523, 531, 568, 599, 600, 681, 702, 704, 722, 724, 1010, 1026, 1028, 1030, 1032, 1070, 1072, 1076

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 & 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 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 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, 256, 346, 355, 393, 399, 401, 402, 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 saturate ½ inch-diameter, cellulose discs (Schleicher & 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 untreated 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, 39, 47, 48, 128, 145, 256, 355, 393, 399, 401, 402, 474, 485, 523, 531, 568, 586

TABLE 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	115-117
24	SCH3	CF3	I	5-bromo-1,2,4-triazol-1-yl
25	SCH3	CF3	I	4-chloroimidazol-1-yl	103-104
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	l,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-trifluoromethylpyrazol-1-yl	107-108
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	imidazal-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-tetrazal-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	201-204
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	>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	83-84
357	H	CF3	I	2H-tetrazol-5-yl	191-194
358	H	CF2CF3	I	2H-tetrazol-5-yl
359	H	CF3	I	2-methyl-2H-tetrazol-5-yl	122-125
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-acetoxybenzy1thio)-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	138-140
378	H	CF3	I	5-bromo-1,2,4-triazol-1-yl
379	H	CF3	I	4-chloroimidazol-1-yl	123-124
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	115-116
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	80-85
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-yI
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-chlorovinyl	imidazol-1-yl	oil
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	165- 167
488	CH2CH3	CF2CF3	I	2H-tetrazol-5-yl
489	CH2CH3	CF3	I	2-methyl-2H-tetrazol-5-yl	112-113
490	CH2CH3	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-y1
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-cbloro-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-yI
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-phenylpyridin-2-yl	CF3	I	1,2,4-triazol-1-yl
540	6-phenylpyridin-2-yl	CF2CF3	I	1,2,4-triazol-1-yl
541	6-phenylpyridin-2-yl	CF3	I	2H-tetrazol-5-yl
542	6-phenylpyridin-2-yl	CF2CF3	I	2H-tetrazol-5-yl
543	6-phenylpyridin-2-yl	CF3	I	2-methyl-2H-tetrazol-5-yl
544	6-phenylpyridin-2-yl	CF2CF3	I	2-methyl-2H-tetrazol-5-yl
545	6-phenylpyridin-2-yl	CF3	I	4-methylimidazol-1-yl
546	6-phenylpyridin-2-yl	CF2CF3	I	4-methylimidazol-1-yl
547	6-phenylpyridin-2-yl	CF3	I	benzimidazol-1-yl
548	6-phenylpyridin-2-yl	CF2CF3	I	benzimidazol-1-yl
549	6-phenylpyridin-2-yl	CF3	I	imidazol-1-yl
550	6-phenylpyridin-2-yl	CF2CF3	I	imidazol-1-yl
551	6-phenylpyridin-2-yl	CF3	F	2H-tetrazol-5-yl
552	6-phenylpyridin-2-yl	CF3	F	2-methyl-2H-tetrazol-5-yl
553	6-phenylpyridin-2-yl	CF3	Cl	2H-tetrazol-5-yl
554	6-phenylpyridin-2-yl	CF3	Cl	2-methyl-2H-tetrazol-5-yl
555	6-phenylpyridin-2-yl	CF3	Br	2H-tetrazol-5-yl
556	6-phenylpyridin-2-yl	CF3	Br	2-methyl-2H-tetrazol-5-yl
557	6-phenylpyridin-2-yl	CF3	Br	imidazol-1-yl	136-138
558	6-methylpyridin-2-yl	CF3	I	1,2,4-triazol-1-yl
559	6-methylpyridin-2-yl	CF2CF3	I	1,2,4-triazol-1-yl
560	6-methylpyridin-2-yl	CF3	I	2H-tetrazol-5-yl
561	6-methylpyridin-2-yl	CF2CF3	I	2H-tetrazol-5-yl
562	6-methylpyridin-2-yl	CF3	I	2-methyl-2H-tetrazol-5-yl
563	6-methylpyridin-2-yl	CF2CF3	I	2-methyl-2H-tetrazol-5-yl
564	6-methylpyridin-2-yl	CF3	I	4-methylimidazol-1-yl
565	6-methylpyridin-2-yl	CF2CF3	I	4-methylimidazol-1-yl
566	6-methylpyridin-2-yl	CF3	I	benzimidazol-1-yl
567	6-methylpyridin-2-yl	CF2CF3	I	benzimidazol-1-yl
568	6-methylpyridin-2-yl	CF3	I	imidazol-1-yl	141-143
569	6-methylpyridin-2-yl	CF2CF3	I	imidazol-1-yl
570	6-methylpyridin-2-yl	CF3	F	2H-tetrazol-5-yl
571	6-methylpyridin-2-yl	CF3	F	2-methyl-2H-tetrazol-5-yl
572	6-methylpyridin-2-yl	CF3	Cl	2H-tetrazol-5-yl
573	6-methylpyridin-2-yl	CF3	Cl	2-methyl-2H-tetrazol-5-yl
574	6-methylpyridin-2-yl	CF3	Br	2H-tetrazol-5-yl
575	6-methylpyridin-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	benzimidazol-1-yl
585	2-oxopyrrolidin-1-yl	CF2CF3	I	benzimidazol-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	117-119
600	CH2CH3	CF3	I	1-methyl-1H-tetrazol-5-yl	96-97
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-tetrazal-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-methylpyridin-4-yl	CF3	I	imidazol-1-yl
650	6-chloropyridin-4-yl	CF3	I	imidazol-1-yl
651	6-trifluoromethylpyridin-4-y	CF3	I	imidazol-1-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-trifluoromethylpyridin-3-y	CF3	I	imidazol-1-yl
656	pyridin-3-yl	CF3	I	imidazol-1-yl
657	6-chloropyridin-2-yl	CF3	I	imidazol-1-yl
658	3-trifluoromethylpyridin-2-y	CF3	I	imidazol-1-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-(trifluoromethyl)phenyl	CF3	I	imidazol-1-yl
672	3-(trifluoromethyl)phenyl	CF3	I	imidazol-1-yl
673	4-(trifluoromethyl)phenyl	CF3	I	imidazol-1-yl
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-yl	CF3	I	imidazol-1-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	F	2H-tetrazol-5-yl
694	CF3	CF3	F	2-methyl-2H-tetrazol-5-yl
695	CF3	CF3	Cl	2H-tetrazol-5-yl
696	CF3	CF3	Cl	2-methyl-2H-tetrazol-5-yl
697	CF3	CF3	Br	2H-tetrazol-5-yl
698	CF3	CF3	Br	2-methyl-2H-tetrazol-5-yl
699	CH═CHCH2Cl	CF3	I	imidazol-1-yl
700	SCH3	CF3	I	4,5-dichloroimidazol-1-yl	114-115
701	SCH3	CF2CF3	I	4,5-dichloroimidazol-1-yl
702	SCH3	CF3	I	3-methyl-1,2,4-triazol-1-yl	84-85
703	SCH3	CF2CF3	I	3-methyl-1,2,4-triazol-1-yl
704	SCH3	CF3	I	3-methyl-1,2,4-triazol-2-yl	150-151
705	SCH3	CF2CF3	I	3-methyl-1,2,4-triazol-2-yl
706	SCH3	CF3	I	2-ethyl-2H-tetrazol-5-yl
707	SCH3	CF2CF3	I	2-ethyl-2H-tetrazol-5-yl
708	SCH3	CF3	I	1-ethyl-1H-tetrazol-5-yl
709	SCH3	CF2CF3	I	1-ethyl-1H-tetrazol-5-yl
710	SCH3	CF3	I	2-isopropyl-2H-tetrazol-5-yl
711	SCH3	CF2CF3	I	2-isopropyl-2H-tetrazol-5-yl
712	SCH3	CF3	I	1-isopropyl-1H-tetrazol-5-yl
713	SCH3	CF2CF3	I	1-isopropyl-1H-tetrazol-5-yl
714	SCH3	CF3	I	2-propargyl-2H-tetrazol-5-yl
715	SCH3	CF2CF3	I	2-propargyl-2H-tetrazol-5-yl
716	SCH3	CF3	I	1-propargyl-1H-tetrazol-5-yl
717	SCH3	CF2CF3	I	1-propargyl-1H-tetrazol-5-yl
718	SCH3	CF3	I	4,5-dimethylimidazol-1-yl	168-170
719	SCH3	CF2CF3	I	4,5-dimethylimidazol-1-yl
720	SCH3	CF3	I	4,5-dibromoimidazol-1-yl	118-120
721	SCH3	CF2CF3	I	4,5-dibromoimidazol-1-yl
722	SCH3	CF3	I	4-trifluoromethylimidazol-1-yl	90-92
723	SCH3	CF2CF3	I	4-trifluoromethylimidazol-1-yl
724	SCH3	CF3	I	4-cyanoimidazol-1-yl	147-149
725	SCH3	CF2CF3	I	4-cyanoimidazol-1-yl
726	SCH3	CF3	I	4,5-diiodoimidazol-1-yl	157-160
727	SCH3	CF2CF3	I	4,5-diiodoimidazol-1-yl
728	SCH2CH3	CF3	I	4,5-dichloroimidazol-1-yl
729	SCH2CH3	CF2CF3	I	4,5-dichloroimidazol-1-yl
730	SCH2CH3	CF3	I	3-methyl-1,2,4-triazol-1-yl
731	SCH2CH3	CF2CF3	I	3-methyl-1,2,4-triazol-1-yl
732	SCH2CH3	CF3	I	3-methyl-1,2,4-triazol-2-yl
733	SCH2CH3	CF2CF3	I	3-methyl-1,2,4-triazol-2-yl
734	SCH2CH3	CF3	I	2-ethyl-2H-tetrazol-5-yl
735	SCH2CH3	CF2CF3	I	2-ethyl-2H-tetrazol-5-yl
736	SCH2CH3	CF3	I	1-ethyl-1H-tetrazol-5-yl
737	SCH2CH3	CF2CF3	I	1-ethyl-1H-tetrazol-5-yI
738	SCH2CH3	CF3	I	2-isopropyl-2H-tetrazol-5-yl
739	SCH2CH3	CF2CF3	I	2-isopropyl-2H-tetrazol-5-yl
740	SCH2CH3	CF3	I	l-isopropyl-1H-tetrazol-5-yl
741	SCH2CH3	CF2CF3	I	1-isopropyl-1H-tetrazol-5-yl
742	SCH2CH3	CF3	I	2-propargyl-2H-tetrazol-5-yl
743	SCH2CH3	CF2CF3	I	2-propargyl-2H-tetrazol-5-yl
744	SCH2CH3	CF3	I	1-propargyl-1H-tetrazol-5-yl
745	SCH2CH3	CF2CF3	I	1-propargyl-1H-tetrazol-5-yl
746	SCH2CH3	CF3	I	4,5-dimethylimidazol-1-yl
747	SCH2CH3	CF2CF3	I	4,5-dimethylimidazol-1-yl
748	SCH2CH3	CF3	I	4,5-dibromoimidazol-1-yl
749	SCH2CH3	CF2CF3	I	4,5-dibromoimidazol-1-yl
750	SCH2CH3	CF3	I	4-trifluoromethylimidazol-1-yl
751	SCH2CH3	CF2CF3	I	4-trifluoromethylimidazol-1-yl
752	SCH2CH3	CF3	I	4-cyanoimidazol-1-yl
753	SCH2CH3	CF2CF3	I	4-cyanoimidazol-1-yl
754	SCH2CH3	CF3	I	4,5-diiodoimidazol-1-yl
755	SCH2CH3	CF2CF3	I	4,5-diiodoimidazol-1-yl
756	SCH(CH3)2	CF3	I	4,5-dichloroimidazol-1-yl
757	SCH(CH3)2	CF2CF3	I	4,5-dichloroimidazol-1-yl
758	SCH(CH3)2	CF3	I	3-methyl-1,2,4-triazol-1-yl
759	SCH(CH3)2	CF2CF3	I	3-methyl-1,2,4-triazol-1-yl
760	SCH(CH3)2	CF3	I	3-methyl-1,2,4-triazol-2-yl
761	SCH(CH3)2	CF2CF3	I	3-methyl-1,2,4-triazol-2-yl
762	SCH(CH3)2	CF3	I	2-ethyl-2H-tetrazol-5-yl
763	SCH(CH3)2	CF2CF3	I	2-ethyl-2H-tetrazol-5-yl
764	SCH(CH3)2	CF3	I	1-ethyl-1H-tetrazol-5-yl
765	SCH(CH3)2	CF2CF3	I	1-ethyl-1H-tetrazol-5-yl
766	SCH(CH3)2	CF3	I	2-isopropyl-2H-tetrazol-5-yl
767	SCH(CH3)2	CF2CF3	I	2-isopropyl-2H-tetrazol-5-yl
768	SCH(CH3)2	CF3	I	1-isopropyl-1H-tetrazol-5-yl
769	SCH(CH3)2	CF2CF3	I	1-isopropyl-1H-tetrazol-5-yl
770	SCH(CH3)2	CF3	I	2-propargyl-2H-tetrazol-5-yl
771	SCH(CH3)2	CF2CF3	I	2-propargyl-2H-tetrazol-5-yl
772	SCH(CH3)2	CF3	I	1-propargyl-1H-tetrazol-5-yl
773	SCH(CH3)2	CF2CF3	I	1-propargyl-1H-tetrazol-5-yl
774	SCH(CH3)2	CF3	I	4,5-dimethylimidazol-1-yl
775	SCH(CH3)2	CF2CF3	I	4,5-dimethylimidazol-1-yl
776	SCH(CH3)2	CF3	I	4,5-dibromoimidazol-1-yl
777	SCH(CH3)2	CF2CF3	I	4,5-dibromoimidazol-1-yl
778	SCH(CH3)2	CF3	I	4-trifluoromethylimidazol-1-yl
779	SCH(CH3)2	CF2CF3	I	4-trifluoromethylimidazol-1-yl
780	SCH(CH3)2	CF3	I	4-cyanoimidazol-1-yl
781	SCH(CH3)2	CF2CF3	I	4-cyanoimidazol-1-yl
782	SCH(CH3)2	CF3	I	4,5-diiodoimidazol-1-yl
783	SCH(CH3)2	CF2CF3	I	4,5-diiodoimidazol-1-yl
784	pyridin-2-yl	CF3	I	4,5-dichloroimidazol-1-yl
785	pyridin-2-yl	CF2CF3	I	4,5-dichloroimidazol-1-yl
786	pyridin-2-yl	CF3	I	3-methyl-1,2,4-triazol-1-yl
787	pyridin-2-yl	CF2CF3	I	3-methyl-1,2,4-triazol-1-yl
788	pyridin-2-yl	CF3	I	3-methyl-1,2,4-triazol-2-yl
789	pyridin-2-yl	CF2CF3	I	3-methyl-1,2,4-triazol-2-yl
790	pyridin-2-yl	CF3	I	2-ethyl-2H-tetrazol-5-yl
791	pyridin-2-yl	CF2CF3	I	2-ethyl-2H-tetrazol-5-yl
792	pyridin-2-yl	CF3	I	1-ethyl-1H-tetrazol-5-yl
793	pyridin-2-yl	CF2CF3	I	1-ethyl-1H-tetrazol-5-yl
794	pyridin-2-yl	CF3	I	2-isopropyl-2H-tetrazol-5-yl
795	pyridin-2-yl	CF2CF3	I	2-isopropyl-2H-tetrazol-5-yl
796	pyridin-2-yl	CF3	I	1-isopropyl-1H-tetrazol-5-yl
797	pyridin-2-yl	CF2CF3	I	1-isopropyl-1H-tetrazol-5-yl
798	pyridin-2-yl	CF3	I	2-propargyl-2H-tetrazol-5-yl
799	pyridin-2-yl	CF2CF3	I	2-propargyl-2H-tetrazol-5-yl
800	pyridin-2-yl	CF3	I	1-propargyl-1H-tetrazol-5-yl
801	pyridin-2-yl	CF2CF3	I	1-propargyl-1H-tetrazol-5-yl
802	pyridin-2-yl	CF3	I	4,5-dimethylimidazol-1-yl
803	pyridin-2-yl	CF2CF3	I	4,5-dimethylimidazol-1-yl
804	pyridin-2-yl	CF3	I	4,5-dibromoimidazol-1-yl
805	pyridin-2-yl	CF2CF3	I	4,5-dibromoimidazol-1-yl
806	pyridin-2-yl	CF3	I	4-trifluoromethylimidazol-1-yl
807	pyridin-2-yl	CF2CF3	I	4-trifluoromethylimidazol-1-yl
808	pyridin-2-yl	CF3	I	4-cyanoimidazol-1-yl
809	pyridin-2-yl	CF2CF3	I	4-cyanoimidazol-1-yl
810	pyridin-2-yl	CF3	I	4,5-diiodoimidazol-1-yl
811	pyridin-2-yl	CF2CF3	I	4,5-diiodoimidazol-1-yl
812	phenyl	CF3	I	4,5-dichloroimidazol-1-yl
813	phenyl	CF2CF3	I	4,5-dichloroimidazol-1-yl
814	phenyl	CF3	I	3-methyl-1,2,4-triazol-1-yl
815	phenyl	CF2CF3	I	3-methyl-1,2,4-triazol-1-yl
816	phenyl	CF3	I	3-methyl-1,2,4-triazol-2-yl
817	phenyl	CF2CF3	I	3-methyl-1,2,4-triazol-2-yl
818	phenyl	CF3	I	2-ethyl-2H-tetrazol-5-yl
819	phenyl	CF2CF3	I	2-ethyl-2H-tetrazol-5-yl
820	phenyl	CF3	I	1-ethyl-1H-tetrazol-5-yl
821	phenyl	CF2CF3	I	1-ethyl-1H-tetrazol-5-yl
822	phenyl	CF3	I	2-isopropyl-2H-tetrazol-5-yl
823	phenyl	CF2CF3	I	2-isopropyl-2H-tetrazol-5-yl
824	phenyl	CF3	I	1-isopropyl-1H-tetrazol-5-yl
825	phenyl	CF2CF3	I	1-isopropyl-1H-tetrazol-5-yl
826	phenyl	CF3	I	2-propargyl-2H-tetrazol-5-yl
827	phenyl	CF2CF3	I	2-propargyl-2H-tetrazol-5-yl
828	phenyl	CF3	I	1-propargyl-1H-tetrazol-5-yl
829	phenyl	CF2CF3	I	1-propargyl-1H-tetrazol-5-yl
830	phenyl	CF3	I	4,5-dimethylimidazol-1-yl
831	phenyl	CF2CF3	I	4,5-dimethylimidazol-1-yl
832	phenyl	CF3	I	4,5-dibromoimidazol-1-yl
833	phenyl	CF2CF3	I	4,5-dibromoimidazol-1-yl
834	phenyl	CF3	I	4-trifluoromethylimidazol-1-yl
835	phenyl	CF2CF3	I	4-trifluoromethylimidazol-1-yl
836	phenyl	CF3	I	4-cyanoimidazol-1-yl
837	phenyl	CF2CF3	I	4-cyanoimidazol-1-yl
838	phenyl	CF3	I	4,5-diiodoimidazol-1-yl
839	phenyl	CF2CF3	I	4,5-diiodoimidazol-1-yl
840	OCH3	CF3	I	4,5-dichloroimidazol-1-yl
841	OCH3	CF2CF3	I	4,5-dichloroimidazol-1-yl
842	OCH3	CF3	I	3-methyl-1,2,4-triazol-1-yl
843	OCH3	CF2CF3	I	3-methyl-1,2,4-triazol-1-yl
844	OCH3	CF3	I	3-methyl-1,2,4-triazol-2-yl
845	OCH3	CF2CF3	I	3-methyl-1,2,4-triazol-2-yl
846	OCH3	CF3	I	2-ethyl-2H-tetrazol-5-yl
847	OCH3	CF2CF3	I	2-ethyl-2H-tetrazol-5-yl
848	OCH3	CF3	I	1-ethyl-1H-tetrazol-5-yl
849	OCH3	CF2CF3	I	1-ethyl-1H-tetrazol-5-yl
850	OCH3	CF3	I	2-isopropyl-2H-tetrazol-5-yl
851	OCH3	CF2CF3	I	2-isopropyl-2H-tetrazol-5-yl
852	OCH3	CF3	I	1-isopropyl-1H-tetrazol-5-yl
853	OCH3	CF2CF3	I	1-isopropyl-lH-tetrazol-5-yl
854	OCH3	CF3	I	2-propargyl-2H-tetrazol-5.yl
855	OCH3	CF2CF3	I	2-propargyl-2H-tetrazol-5-yl
856	OCH3	CF3	I	1-propargyl-1H-tetrazol-5-yl
857	OCH3	CF2CF3	I	1-propargyl-1H-tetrazol-5-yl
858	OCH3	CF3	I	4,5-dimethylimidazol-1-yl
859	OCH3	CF2CF3	I	4,5-dimethylimidazol-1-yl
860	OCH3	CF3	I	4,5-dibromoimidazol-1-yl
861	OCH3	CF2CF3	I	4,5-dibromoimidazol-1-yl
862	OCH3	CF3	I	4-trifluoromethylimidazol-1-yl
863	OCH3	CF2CF3	I	4-trifluoromethylimidazol-1-yl
864	OCH3	CF3	I	4-cyanoimidazol-1-yl
865	OCH3	CF2CF3	I	4-cyanoimidazol-1-yl
866	OCH3	CF3	I	4,5-diiodoimidazol-1-yl
867	OCH3	CF2CF3	I	4,5-diiodoimidazol-1-yl
868	OCH2C≡CH	CF3	I	4,5-dichloroimidazol-1-yl
869	OCH2C≡CH	CF2CF3	I	4,5-dichloroimidazol-1-yl
870	OCH2C≡CH	CF3	I	3-methyl-1,2,4-triazol-1-yl
871	OCH2C≡CH	CF2CF3	I	3-methyl-1,2,4-triazol-1-yl
872	OCH2C≡CH	CF3	I	3-methyl-1,2,4-triazol-2-yl
873	OCH2C≡CH	CF2CF3	I	3-methyl-1,2,4-triazol-2-yl
874	OCH2C≡CH	CF3	I	2-ethyl-2H-tetrazol-5-yl
875	OCH2C≡CH	CF2CF3	I	2-ethyl-2H-tetrazol-5-yl
876	OCH2C≡CH	CF3	I	1-ethyl-1H-tetrazol-5-yl
877	OCH2C≡CH	CF2CF3	I	1-ethyl-1H-tetrazol-5-yl
878	OCH2C≡CH	CF3	I	2-isopropyl-2H-tetrazol-5-yl
879	OCH2C≡CH	CF2CF3	I	2-isopropyl-2H-tetrazol-5-yl
880	OCH2C≡CH	CF3	I	1-isopropyl-1H-tetrazol-5-yl
881	OCH2C≡CH	CF2CF3	I	1-isopropyl-1H-tetrazol-5-yl
882	OCH2C≡CH	CF3	I	2-propargyl-2H-tetrazol-5-yl
883	OCH2C≡CH	CF2CF3	I	2-propargyl-2H-tetrazol-5-yl
884	OCH2C≡CH	CF3	I	1-propargyl-1H-tetrazol-5-yl
885	OCH2C≡CH	CF2CF3	I	1-propargyl-1H-tetrazol-5-yl
886	OCH2C≡CH	CF3	I	4,5-dimethylimidazol-1-yl
887	OCH2C≡CH	CF2CF3	I	4,5-dimethylimidazol-1-yl
888	OCH2C≡CH	CF3	I	4,5-dibromoimidazol-1-yl
889	OCH2C≡CH	CF2CF3	I	4,5-dibromoimidazol-1-yl
890	OCH2C≡CH	CF3	I	4-trifluoromethylimidazol-1-yl
891	OCH2C≡CH	CF2CF3	I	4-trifluoromethylimidazol-1-yl
892	OCH2C≡CH	CF3	I	4-cyanoimidazol-1-yl
893	OCH2C≡CH	CF2CF3	I	4-cyanoimidazol-1-yl
894	OCH2C≡CH	CF3	I	4,5-diiodoimidazol-1-yl
895	OCH2C≡CH	CF2CF3	I	4,5-diiodoimidazol-1-yl
896	OCH2CH3	CF3	I	4,5-dichloroimidazol-1-yl
897	OCH2CH3	CF2CF3	I	4,5-dichloroimidazol-1-yl
898	OCH2CH3	CF3	I	3-methyl-1,2,4-triazol-1-yl
899	OCH2CH3	CF2CF3	I	3-methyl-1,2,4-triazol-1-yl
900	OCH2CH3	CF3	I	3-methyl-1,2,4-triazol-2-yl
901	OCH2CH3	CF2CF3	I	3-methyl-1,2,4-triazol-2-yl
902	OCH2CH3	CF3	I	2-ethyl-2H-tetrazol-5-yl
903	OCH2CH3	CF2CF3	I	2-ethyl-2H-tetrazol-5-yl
904	OCH2CH3	CF3	I	1-ethyl-1H-tetrazol-5-yl
905	OCH2CH3	CF2CF3	I	1-ethyl-1H-tetrazol-5-yl
906	OCH2CH3	CF3	I	2-isopropyl-2H-tetrazol-5-yl
907	OCH2CH3	CF2CF3	I	2-isopropyl-2H-tetrazol-5-yl
908	OCH2CH3	CF3	I	1-isopropyl-1H-tetrazol-5-yl
909	OCH2CH3	CF2CF3	I	1-isopropyl-1H-tetrazol-5-yl
910	OCH2CH3	CF3	I	2-propargyl-2H-tetrazol-5-yl
911	OCH2CH3	CF2CF3	I	2-propargyl-2H-tetrazol-5-yl
912	OCH2CH3	CF3	I	1-propargyl-1H-tetrazol-5-yl
913	OCH2CH3	CF2CF3	I	1-propargyl-1H-tetrazol-5-yl
914	OCH2CH3	CF3	I	4,5-dimethylimidazol-1-yl
915	OCH2CH3	CF2CF3	I	4,5-dimethylimidazol-1-yl
916	OCH2CH3	CF3	I	4,5-dibromoimidazol-1-yl
917	OCH2CH3	CF2CF3	I	4,5-dibromoimidazol-1-yl
918	OCH2CH3	CF3	I	4-trifluoromethylimidazol-1-yl
919	OCH2CH3	CF2CF3	I	4-trifluoromethylimidazol-1-yl
920	OCH2CH3	CF3	I	4-cyanoimidazol-1-yl
921	OCH2CH3	CF2CF3	I	4-cyanoimidazol-1-yl
922	OCH2CH3	CF3	I	4,5-diiodoimidazol-1-yl
923	OCH2CH3	CF2CF3	I	4,5-diiodoimidazol-1-yl
924	OCH2CH2CH3	CF3	I	4,5-dichloroimidazol-1-yl
925	OCH2CH2CH3	CF2CF3	I	4,5-dichloroimidazol-1-yl
926	OCH2CH2CH3	CF3	I	3-methyl-1,2,4-triazol-1-yl
927	OCH2CH2CH3	CF2CF3	I	3-methyl-1,2,4-triazol-1-yl
928	OCH2CH2CH3	CF3	I	3-methyl-1,2,4-triazol-2-yl
929	OCH2CH2CH3	CF2CF3	I	3-methyl-1,2,4-triazol-2-yl
930	OCH2CH2CH3	CF3	I	2-ethyl-2H-tetrazol-5-yl
931	OCH2CH2CH3	CF2CF3	I	2-ethyl-2H-tetrazol-5-yl
932	OCH2CH2CH3	CF3	I	1-ethyl-1H-tetrazol-5-yl
933	OCH2CH2CH3	CF2CF3	I	1-ethyl-1H-tetrazol-5-yl
934	OCH2CH2CH3	CF3	I	2-isopropyl-2H-tetrazol-5-yl
935	OCH2CH2CH3	CF2CF3	I	2-isopropyl-2H-tetrazol-5-yl
936	OCH2CH2CH3	CF3	I	1-isopropyl-1H-tetrazol-5-yl
937	OCH2CH2CH3	CF2CF3	I	1-isopropyl-1H-tetrazol-5-yl
938	OCH2CH2CH3	CF3	I	2-propargyl-2H-tetrazol-5-yl
939	OCH2CH2CH3	CF2CF3	I	2-propargyl-2H-tetrazol-5-yl
940	OCH2CH2CH3	CF3	I	1-propargyl-1H-tetrazol-5-yl
941	OCH2CH2CH3	CF2CF3	I	1-propargyl-1H-tetrazol-5-yl
942	OCH2CH2CH3	CF3	I	4,5-dimethylimidazol-1-yl
943	OCH2CH2CH3	CF2CF3	I	4,5-dimethylimidazol-1-yl
944	OCH2CH2CH3	CF3	I	4,5-dibromoimidazol-1-yl
945	OCH2CH2CH3	CF2CF3	I	4,5-dibromoimidazol-1-yl
946	OCH2CH2CH3	CF3	I	4-trifluoromethylimidazol-1-yl
947	OCH2CH2CH3	CF2CF3	I	4-trifluoromethylimidazol-1-yl
948	OCH2CH2CH3	CF3	I	4-cyanoimidazol-1-yl
949	OCH2CH2CH3	CF2CF3	I	4-cyanoimidazol-1-yl
950	OCH2CH2CH3	CF3	I	4,5-diiodoimidazol-1-yl
951	OCH2CH2CH3	CF2CF3	I	4,5-diiodoimidazol-1-yl
952	OCH2CF2H	CF3	I	4,5-dichloroimidazol-1-yl
953	OCH2CF2H	CF2CF3	I	4,5-dichloroimidazol-1-yl
954	OCH2CF2H	CF3	I	3-methyl-1,2,4-triazol-1-yl
955	OCH2CF2H	CF2CF3	I	3-methyl-1,2,4-triazol-1-yl
956	OCH2CF2H	CF3	I	3-methyl-1,2,4-triazol-2-yl
957	OCH2CF2H	CF2CF3	I	3-methyl-1,2,4-triazol-2-yl
958	OCH2CF2H	CF3	I	2-ethyl-2H-tetrazol-5-yl
959	OCH2CF2H	CF2CF3	I	2-ethyl-2H-tetrazol-5-yl
960	OCH2CF2H	CF3	I	1-ethyl-1H-tetrazol-5-yl
961	OCH2CF2H	CF2CF3	I	1-ethyl-1H-tetrazol-5-yl
962	OCH2CF2H	CF3	I	2-isopropyl-2H-tetrazol-5-yl
963	OCH2CF2H	CF2CF3	I	2-isopropyl-2H-tetrazol-5-yl
964	OCH2CF2H	CF3	I	1-isopropyl-1H-tetrazol-5-yl
965	OCH2CF2H	CF2CF3	I	1-isopropyl-1H-tetrazol-5-yl
966	OCH2CF2H	CF3	I	2-propargyl-2H-tetrazol-5-yl
967	OCH2CF2H	CF2CF3	I	2-propargyl-2H-tetrazol-5-yl
968	OCH2CF2H	CF3	I	1-propargyl-1H-tetrazol-5-yl
969	OCH2CF2H	CF2CF3	I	1-propargyl-1H-tetrazol-5-yl
970	OCH2CF2H	CF3	I	4,5-dimethylimidazol-1-yl
971	OCH2CF2H	CF2CF3	I	4,5-dimethylimidazol-1-yl
972	OCH2CF2H	CF3	I	4,5-dibromoimidazol-1-yl
973	OCH2CF2H	CF2CF3	I	4,5-dibromoimidazol-1-yl
974	OCH2CF2H	CF3	I	4-trifluoromethylimidazol-1-yl
975	OCH2CF2H	CF2CF3	I	4-trifluoromethylimidazol-1-yl
976	OCH2CF2H	CF3	I	4-cyanoimidazol-1-yl
977	OCH2CF2H	CF2CF3	I	4-cyanoimidazol-1-yl
978	OCH2CF2H	CF3	I	4,5-diiodoimidazol-1-yl
979	OCH2CF2H	CF2CF3	I	4,5-dilodoimidazol-1-yl
980	OCH(CH3)2	CF3	I	4,5-dichloroimidazol-1-yl
981	OCH(CH3)2	CF2CF3	I	4,5-dichloroimidazol-1-yl
982	OCH(CH3)2	CF3	I	3-methyl-1,2,4-triazol-1-yl
983	OCH(CH3)2	CF2CF3	I	3-methyl-1,2,4-triazol-1-yl
984	OCH(CH3)2	CF3	I	3-methyl-1,2,4-triazol-2-yl
985	OCH(CH3)2	CF2CF3	I	3-methyl-1,2,4-triazol-2-yl
986	OCH(CH3)2	CF3	I	2-ethyl-2H-tetrazol-5-yl
987	OCH(CH3)2	CF2CF3	I	2-ethyl-2H-tetrazol-5-yl
988	OCH(CH3)2	CF3	I	1-ethyl-1H-tetrazol-5-yl
989	OCH(CH3)2	CF2CF3	I	1-ethyl-1H-tetrazol-5-yl
990	OCH(CH3)2	CF3	I	2-isopropyl-2H-tetrazol-5-yl
991	OCH(CH3)2	CF2CF3	I	2-isopropyl-2H-tetrazol-5-yl
992	OCH(CH3)2	CF3	I	1-isopropyl-1H-tetrazol-5-yl
993	OCH(CH3)2	CF2CF3	I	1-isopropyl-1H-tetrazol-5-yl
994	OCH(CH3)2	CF3	I	2-propargyl-2H-tetrazol-5-yl
995	OCH(CH3)2	CF2CF3	I	2-propargyl-2H-tetrazol-5-yl
996	OCH(CH3)2	CF3	I	1-propargyl-1H-tetrazol-5-yl
997	OCH(CH3)2	CF2CF3	I	1-propargyl-1H-tetrazol-5-yl
998	OCH(CH3)2	CF3	I	4,5-dimethylimidazol-1-yl
999	OCH(CH3)2	CF2CF3	I	4,5-dimethylimidazol-1-yl
1000	OCH(CH3)2	CF3	I	4,5-dibromoimidazol-1-yl
1001	OCH(CH3)2	CF2CF3	I	4,5-dibromoimidazol-1-yl
1002	OCH(CH3)2	CF3	I	4-trifluoromethylimidazol-1-yl
1003	OCH(CH3)2	CF2CF3	I	4-trifluoromethylimidazol-1-yl
1004	OCH(CH3)2	CF3	I	4-cyanoimidazol-1-yl
1005	OCH(CH3)2	CF2CF3	I	4-cyanoimidazol-1-yl
1006	OCH(CH3)2	CF3	I	4,5-diiodoimidazol-1-yl
1007	OCH(CH3)2	CF2CF3	I	4,5-diiodoimidazol-1-yl
1008	H	CF3	I	4,5-dichloroimidazol-1-yl
1009	H	CF2CF3	I	4,5-dichloroimidazol-1-yl
1010	H	CF3	I	3-methyl-1,2,4-triazol-1-yl	109-111
1011	H	CF2CF3	I	3-methyl-1,2,4-triazol-1-yl
1012	H	CF3	I	3-methyl-1,2,4-triazol-2-yl
1013	H	CF2CF3	I	3-methyl-1,2,4-triazol-2-yl
1014	H	CF3	I	2-ethyl-2H-tetrazol-5-yl
1015	H	CF2CF3	I	2-ethyl-2H-tetrazol-5-yl
1016	H	CF3	I	1-ethyl-1H-tetrazol-5-yl
1017	H	CF2CF3	I	1-ethyl-1H-tetrazol-5-yl
1018	H	CF3	I	2-isopropyl-2H-tetrazol-5-yl
1019	H	CF2CF3	I	2-isopropyl-2H-tetrazol-5-yl
1020	H	CF3	I	1-isopropyl-1H-tetrazol-5-yl
1021	H	CF2CF3	I	1-isopropyl-1H-tetrazol-5-yl
1022	H	CF3	I	2-propargyl-2H-tetrazol-5-yl
1023	H	CF2CF3	I	2-propargyl-2H-tetrazol-5-yl
1024	H	CF3	I	1-propargyl-1H-tetrazol-5-yl
1025	H	CF2CF3	I	1-propargyl-1H-tetrazol-5-yl
1026	H	CF3	I	4,5-dimethylimidazol-1-yl	145-148
1027	H	CF2CF3	I	4,5-dimethylimidazol-1-yl
1028	H	CF3	I	4,5-dibromoimidazol-1-yl	88-90
1029	H	CF2CF3	I	4,5-dibromoimidazol-1-yl
1030	H	CF3	I	4-trifluoromethylimidazol-1-yl	109-110
1031	H	CF2CF3	I	4-trifluoromethylimidazol-1-yl
1032	H	CF3	I	4-cyanoimidazol-1-yl	117-119
1033	H	CF2CF3	I	4-cyanoimidazol-1-yl
1034	H	CF3	I	4,5-diiodoimidazol-1-yl
1035	H	CF2CF3	I	4,5-diiodoimidazol-1-yl
1036	CH3	CF3	I	4,5-dichloroimidazol-1-yl
1037	CH3	CF2CF3	I	4,5-dichloroimidazol-1-yl
1038	CH3	CF3	I	3-methyl-1,2,4-triazol-1-yl	107-110
1039	CH3	CF2CF3	I	3-methyl-1,2,4-triazol-1-yl
1040	CH3	CF3	I	3-methyl-1,2,4-triazol-2-yl	146-148
1041	CH3	CF2CF3	I	3-methyl-1,2,4-triazol-2-yl
1042	CH3	CF3	I	2-ethyl-2H-tetrazol-5-yl
1043	CH3	CF2CF3	I	2-ethyl-2H-tetrazol-5-yl
1044	CH3	CF3	I	1-ethyl-1H-tetrazol-5-yl
1045	CH3	CF2CF3	I	1-ethyl-1H-tetrazol-5-yl
1046	CH3	CF3	I	2-isopropyl-2H-tetrazol-5-yl
1047	CH3	CF2CF3	I	2-isopropyl-2H-tetrazol-5-yl
1048	CH3	CF3	I	1-isopropyl-1H-tetrazol-5-yl
1049	CH3	CF2CF3	I	1-isopropyl-1H-tetrazol-5-yl
1050	CH3	CF3	I	2-propargyl-2H-tetrazol-5-yl
1051	CH3	CF2CF3	I	2-propargyl-2H-tetrazol-5-yl
1052	CH3	CF3	I	1-propargyl-1H-tetrazol-5-yl
1053	CH3	CF2CF3	I	1-propargyl-1H-tetrazol-5-yl
1054	CH3	CF3	I	4,5-dimethylimidazol-1-yl	132-135
1055	CH3	CF2CF3	I	4,5-dimethylimidazol-1-yl
1056	CH3	CF3	I	4,5-dibromoimidazol-1-yl
1057	CH3	CF2CF3	I	4,5-dibromoimidazol-1-yl
1058	CH3	CF3	I	4-trifluoromethylimidazol-1-yl	103-106
1059	CH3	CF2CF3	I	4-trifluoromethylimidazol-1-yl
1060	CH3	CF3	I	4-cyanoimidazol-1-yl	145-147
1061	CH3	CF2CF3	I	4-cyanoimidazol-1-yl
1062	CH3	CF3	I	4,5-diiodoimidazol-1-yl	200-202
1063	CH3	CF2CF3	I	4,5-diiodoimidazol-1-yl
1064	CH2CH3	CF3	I	4,5-dichloroimidazol-1-yl
1065	CH2CH3	CF2CF3	I	4,5-dichloroimidazol-1-yl
1066	CH2CH3	CF3	I	3-methyl-1,2,4-triazol-1-yl
1067	CH2CH3	CF2CF3	I	3-methyl-1,2,4-triazol-1-yl
1068	CH2CH3	CF3	I	3-methyl-1,2,4-triazol-2-yl
1069	CH2CH3	CF2CF3	I	3-methyl-1,2,4-triazol-2-yl
1070	CH2CH3	CF3	I	2-ethyl-2H-tetrazol-5-yl	60-61
1071	CH2CH3	CF2CF3	I	2-ethyl-2H-tetrazol-5-yl
1072	CH2CH3	CF3	I	1-ethyl-1H-tetrazol-5-yl	99-100
1073	CH2CH3	CF2CF3	I	1-ethyl-1H-tetrazol-5-yl
1074	CH2CH3	CF3	I	2-isopropyl-2H-tetrazol-5-yl	63-64
1075	CH2CH3	CF2CF3	I	2-isopropyl-2H-tetrazol-5-yl
1076	CH2CH3	CF3	I	1-isopropyl-1H-tetrazol-5-yl	98-99
1077	CH2CH3	CF2CF3	I	1-isopropyl-1H-tetrazol-5-yl
1078	CH2CH3	CF3	I	2-propargyl-2H-tetrazol-5-yl	64
1079	CH2CH3	CF2CF3	I	2-propargyl-2H-tetrazol-5-yl
1080	CH2CH3	CF3	I	1-propargyl-1H-tetrazol-5-yl	oil
1081	CH2CH3	CF2CF3	I	1-propargyl-1H-tetrazol-5-yl
1082	CH2CH3	CF3	I	4,5-dimethylimidazol-1-yl
1083	CH2CH3	CF2CF3	I	4,5-dimethylimidazol-1-yl
1084	CH2CH3	CF3	I	4,5-dibromoimidazol-1-yl
1085	CH2CH3	CF2CF3	I	4,5-dibromoimidazol-1-yl
1086	CH2CH3	CF3	I	4-trifluoromethylimidazol-1-yl
1087	CH2CH3	CF2CF3	I	4-trifluoromethylimidazll-1-yl
1088	CH2CH3	CF3	I	4-cyanoimidazol-1-yl
1089	CH2CH3	CF2CF3	I	4-cyanoimidazol-1-yl
1090	CH2CH3	CF3	I	4,5-diiodoimidazol-1-yl
1091	CH2CH3	CF2CF3	I	4,5-diiodoimidazol-1-yl
1092	CF3	CF3	I	4,5-dichloroimidazol-1-yl
1093	CF3	CF2CF3	I	4,5-dichloroimidazol-1-yl
1094	CF3	CF3	I	3-methyl-1,2,4-triazol-1-yl
1095	CF3	CF2CF3	I	3-methyl-1,2,4-triazol-1-yl
1096	CF3	CF3	I	3-methyl-1,2,4-triazol-2-yl
1097	CF3	CF2CF3	I	3-methyl-1,2,4-triazol-2-yl
1098	CF3	CF3	I	2-ethyl-2H-tetrazol-5-yl
1099	CF3	CF2CF3	I	2-ethyl-2H-tetrazol-5-yl
1100	CF3	CF3	I	1-ethyl-1H-tetrazol-5-yl
1101	CF3	CF2CF3	I	1-ethyl-1H-tetrazol-5-yl
1102	CF3	CF3	I	2-isopropyl-2H-tetrazol-5-yl
1103	CF3	CF2CF3	I	2-isopropyl-2H-tetrazol-5-yl
1104	CF3	CF3	I	1-isopropyl-1H-tetrazol-5-yl
1105	CF3	CF2CF3	I	1-isopropyl-1H-tetrazol-5-yl
1106	CF3	CF3	I	2-propargyl-2H-tetrazol-5-yl
1107	CF3	CF2CF3	I	2-propargyl-2H-tetrazol-5-yl
1108	CF3	CF3	I	1-propargyl-1H-tetrazol-5-yl
1109	CF3	CF2CF3	I	1-propargyl-1H-tetrazol-5-yl
1110	CF3	CF3	I	4,5-dimethylimidazol-1-yl
1111	CF3	CF2CF3	I	4,5-dimethylimidazol-1-yl
1112	CF3	CF3	I	4,5-dibromoimidazol-1-yl
1113	CF3	CF2CF3	I	4,5-dibromoimidazol-1-yl
1114	CF3	CF3	I	4-trifluoromethylimidazol-1-yl
1115	CF3	CF2CF3	I	4-trifluoromethylimidazol-1-yl
1116	CF3	CF3	I	4-cyanoimidazol-1-yl
1117	CF3	CF2CF3	I	4-cyanoimidazol-1-yl
1118	CF3	CF3	I	4,5-diiodoimidazol-1-yl
1119	CF3	CF2CF3	I	4,5-diiodoimidazol-1-yl

Claims

1. Pyrimidine derivatives represented by the formula (1),

2. A fungicide for agricultural and horticultural use, comprising one or more of the pyrimidine derivatives represented by a formula (1)