WO2005019207A1 - Fungicidal pyrimidine derivatives - Google Patents

Fungicidal pyrimidine derivatives Download PDF

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Publication number
WO2005019207A1
WO2005019207A1 PCT/US2004/020114 US2004020114W WO2005019207A1 WO 2005019207 A1 WO2005019207 A1 WO 2005019207A1 US 2004020114 W US2004020114 W US 2004020114W WO 2005019207 A1 WO2005019207 A1 WO 2005019207A1
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Prior art keywords
tetrazol
triazol
och
halogen
optionally substituted
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PCT/US2004/020114
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French (fr)
Inventor
Charles R. Semer, Iv
Thomas A. Kucharek
Yuki Nakagawa
Sergey Bobrov
Masahiro Haramoto
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Nippon Soda Co Ltd
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Nippon Soda Co Ltd
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Priority claimed from US10/642,552 external-priority patent/US6818631B1/en
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/38—One sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/56—One oxygen atom and one sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings

Definitions

  • Pyrimidinones of structure 1-2 can be synthesized by condensation of a ⁇ -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.
  • Dicarboxyimide Fungicides Oxycarboxine, mepronyl, flutolanil, techlofthalam, trichlamide, pencycuron, etc. Acyl Alanine Fungicides Metalaxyl, oxadixyl, furalaxyl etc.
  • 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 201 and high humidity with repeated lighting of 12 hours intervals, and the apple trees are allowed to stand in the room for two weeks.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Fungicidal pyrimidine derivatives and the use as a fungicide of the compounds of formula (1): wherein R1 is H, C1-C6 alkyl, C2-C 6 alkenyl, C2-C6 alkynyl, C3-C6cycloalkyl, C1 C 6 alkoxy, C3-C 6 cycloalkoxy, C1-C6alkylthio, C1-C 6 alkylsulfinyl, 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-C 6 alkyl, C2-C6alkenyl or C2-C 6 alkynyl 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-l-yl, 1,2,3-triazol-l-yl, 1,2,3-triazol-2-yl, 1,2,4-triazol-l-yl, 1,2,4-triazol-4-yl, benzimidazol-l-yl or tetrazol-5-yl groups, (being optionally substituted by one or more of substituents).

Description

Fungicidal Pyrimidine derivatives 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, IP 337943 have herbicidal and plant growth regulatory properties, US 4474599 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 US 3149109 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):
Figure imgf000002_0001
<1 > , Wherein R1 is H, Ci-Cealkyl (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), Cx-Cgalkoxy (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), C^Cealkylthio (being optionally substituted by one or more of halogen), Ci-Cealkylsulfinyl (being optionally substituted by one or more of halogen), Ci-Cβalkylsulfonyl (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(0)R5, R2 is haloCrCealkyl,
R3 is halogen, C2-C6alkenyl or C2-C6alkynyl groups, (being optionally substituted by one or more of halogen),
R4 and R5 are, independently, H, Cx-Cealkyl (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-l-yl, l,2,3-triazol-2-yl, 1,2,4-triazol-l-yl, l,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 aetive 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):
Figure imgf000004_0001
(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), Ci-Cealkylthio (being optionally substituted by one or more of halogen), Cx-Cgalkylsulfinyl (being optionally substituted by one or more of halogen), CrC6alkylsulfonyl (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(0)R5, R2 is haloC Cealkyl, R3 is halogen, C2-C6alkenyl or C2-C6alkynyl groups, (being optionally substituted by one or more of halogen), R4 and R5 are, independently, H, Cx- C6alkyl (being optionally substituted hy 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-l-yl, l,2,3-triazol-2-yl, 1,2,4-triazol-l-yl, l,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.
SCHEME 1
Figure imgf000005_0001
1 -1 1-2
halogenating agent
Figure imgf000005_0002
1-3 1 -4 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 thμs 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=C1, 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.
SCHEME 2
Figure imgf000006_0001
2-1 2-2
alkylating agent halogenating agent
Figure imgf000006_0002
2-3 chlorination
Figure imgf000006_0003
Figure imgf000006_0004
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.
SCHEME 3
Figure imgf000007_0001
3-1 3-2
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-chloiOpyrimidine of structure 3-2.
SCHEME 4
Figure imgf000007_0002
4-1 4-2
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
Figure imgf000008_0001
5-1 5-2 5-3
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.
SCHEME 6
Figure imgf000008_0002
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.
SCHEME 7
Figure imgf000009_0001
7-4
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-HC1 under reflux to give a 5-alkenylpyrimidinone of structure 7-4.
SCHEME 8
Figure imgf000009_0002
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)paHadium(0), dichlorobis(triphenylphosphine)paUadium(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.
SCHEME 9 n-BuLi fluorinating agent
Figure imgf000010_0001
Figure imgf000010_0002
9-1 9-2
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.
SCHEME 10
Figure imgf000010_0003
10-1 10-2 10-3
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.
SCHEME 11
NalsL
Figure imgf000011_0001
Figure imgf000011_0002
11-3 11-4 11 -5
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. ydroxide, 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 orvzae) Sheath blight (Rhizoctonia solani) Bakanae disease (Gibberella fuiikuroi) Helminthosporium leaf spot (Cochliobolus miyabeanus)
Barley Loose smut ( Ustϊlago n uda)
Wheat Scab (Gibberella zeae) Leaf rust (Puccinia recondita) Eye spot (Pseudocercosporella herpotrichoides) Glume blotch (Leptosphaeria nodorurώ Powdery mildew (Ervsiphe graminis fsp. 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 (βclerotinia 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 fa wcetti) Blue mlold (Penicillium italicum) Turf Sclerotinia snow blight (β erotinia 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-trifl.uoromethyl-3H-pyrimidin-4-one (20.0g) was dissolved in acetonitrile (100ml) and N-bromosuccinimide (18.7g) 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 (25.3g) as colorless needles, mp 215-216°C. Example 2: 5-Iodo-2-isopropylthio-6-trifl.uoromethyl-3H-pyrimidin-4-one: 2-Isopropylthio-6-trifluoromethyl-3H-pyrimidin-4-one (23.3g) was dissolved in acetonitrile (230ml) and N-iodosuccinimide (24.2g) 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-trifl.uoromethyl-3H-pyrimidin-4-one (34.8g) 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 (15.0g) was dissolved in DMF (150ml) and N-iodosuccinimide (33.6g) 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 (150ml), 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-trifl.uoromethyl-3H-pyrimidin-4-one. It was recrystallized from toluene as pale brown needles (10.2g), mp 186-187°C. Example 4: 4-Chloro-5-iodo-2-methylthio-6-trifluoromethylpyrimidine: 5-Iodo-2-methylthio-6-trifluoromethyl-3H-pyrimidin-4-one (11.8g) was dissolved in phosphoryl chloride (40ml) and phosphorous pentachloride (7.9g) 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 (12.2g) as pale brown crystalline solid, mp 55-56°C Example 5: 4-Chloro-5-iodo-2-isopropylsulfonyl-6-trifiuoromethypyrimidine: 4-Chloro-5-iodo-2-isopropylthio-6-trifluoromethypyrimidine (15.0g) was dissolved in dichloromethane (150ml) and m-chloroperbenzoic acid (75%, 27. lg) 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 (14.3g) as pale yellow crystalline solid, mp 67-69°C. Example 6: 5-Iodo-4-methoxy-2-methyl-6-trifl.uoromethylpyrimidine: 4-Chloro-5-iodo-2-methyl-6-trifl.uoromethylpyrimidine (23.0g) was dissolved in methanol (150ml) and sodium methoxide (30% methanol solution, 12.8g) 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 (13.0g) 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-trifluoromethylpyriinidine (5.0g) was dissolved in DMF (50ml) and N,N-diisopropylethylamine (6.5g), copper(t) iodide (0.3g), dichlorobis(triphenylphosphine)palladium(II) (1.12g) and trimethylsilylacetylene (15.4g) 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) (200ml). 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 (5.3g) as pale yellow oil. This crude 4-methoxy-2- methyl-6-trifl.uoromethyl-5-trimethylsilylethynylpyrimidine (5.2g) was dissolved in THF (100ml) and tetrabutylammonium fluoride (1M THF solution, 18ml) 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 (1.92g) as colorless crystalline solid, mp 77°C. Example 8: 5-(l-Chlorovinyl)-2-methyl-6-trifluoromethyl-3H-pyrimidin-4-one: 5-ethynyl-4-methoxy-2-methyl-6-trifl.uoromethylpyrimidine (1.92g) was added 6N-HC1 (20ml) 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- (l-chlorovinyl)-2-methyl-6-trifluoromethyl-3H-pyrimidin-4-one (1.62g) as colorless crystalline solid, mp 164-166°C. Example 9: 5-Fluoro-2,4-dimethoxy-6-trifluoromethypyrimidine: 5-Bromo-2,4-dimethoxy-6-trifluoromethypyrimidine (0.50g) was dissolved in dry THF (5ml) at room temperature under nitrogen atmosphere. The mixture was cooled to -70°C, and then added n-butyllithium (1.6M in hexane, 1.2ml) dropwise below -50°C, and then added N-fluoro-bisphenylsulfonimide (0.6 lg) THF (5ml) 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 (0.30g) as pale yeUow oil, ESI-MS 227 |M+H]+. Example 10: 4-Cyano-5-iodo-2-methylthio-6-trifluoromethylpyrimidine: 4-Chloro-5-iodo-2-methylthio-6-trifluoromethylpyrimidine (5.00g) was dissolved in propionitrile (125ml) and 4-(dimethylamino)-pyridine (1.81g) 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 (1.04g) water (10ml) 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 (2.56g) as yellow solid, mp 68-69°C. Example 11: 4-Imidazol- l-yl-5-iodo-2-isopropylthio-6-trifluoromethyl- pyrimidine:
4-Chloro-5-iodo-2-isopropylthio-6-trifluoromethylpyrimidine (3.0g) was dissolved in acetonitrile (30ml) and imidazole (1.6g) 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-l-yl-5-iodo-2-isopropyltbio-6-trifluoromethyl-pyrimidine. It was recrystallized from methanol-water mixture as colorless needles (2.6 lg), mp 118-120°C. Example 12: Ethyl l-(5-iodo-2-isopropylthio-6-trifluoromethylpyrimidin-4-yl)- 3-trifluoromethyl-lH-pyrazole-4-carboxylate: 4-Chloro-5-iodo-2:isopropylthio-6-trifl.uoromethylpyrimidine (0.30g) was dissolved in dimethylsulfoxide (3.0ml) and ethyl 3-trifluoromethyl-lH-pyrazole-4-carboxylate (0.16g) and l,8-diazabicyclo-[5,4,0]-undec-7-ene (0.12g) was added at room temperature with stirring. The mixture was heated to 80°C and stirred for 2hr. 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 l-(5-iodo-2-isopropylthio- 6-trifl.uoromethylpyrimidin-4-yl)-3-trifluoromethyl- lH-pyrazole-4-carboxylate (0.30g) as colorless crystalline solid, mp 107-108°C. Example 13: 4-Imidazol- l-yl-5-iodo-2-prop-2-ynyloxy-6-triffuoromethyl- pyrimidine:
4-Chloro-5-iodo-2-isopropylsulfonyl-6-trifl.uoromethypyrimidine (0.79g) was dissolved in tetrahydrofuran (5.0ml) and added propargyl alcohol (O.llg). The mixture was cooled to ice bath temperature and added sodium hydride (oily 80%, 57mg). The mixture was stirred at that temperature for 10 minutes, and then added imidazole (0.39g) 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-l-yl-5-iodo- 2-prop-2-ynyloxy-6-trifluoromethyl- pyrimidine (0.20g) as colorless crystalline solid, mp 128-129°C. Example 14: l-(4-Imidazol- l-yl-5-iodo-6-trifluoromethylpyrimidm-2-yl)- pyrrolidin-2-one:
4-Chloro-5-iodo-2-isopropylsulfonyl-6-trifluoromethypyrimidine (0.50g) was dissolved in tetrahydrofuran (5.0ml) and added 2-pyrrolidinone (0.10g). The mixture was cooled to ice bath temperature and added sodium hydride (oily 80%, 36mg). The mixture was stirred at that temperature for 10 minutes, and then added imidazole (0.25g) 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 l-(4-imidazol-l-yl-5-iodo-6-trifluoromethylpyrimidin-2-yl)- pyrrolidin-2-one (0.20g) 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 (0.50g) was dissolved in isopropanol (5ml) and added water (10ml), sodium azide (0.19g) and zinc bromide (0.16g) with stirring in room temperature. The mixture was refluxed for 3 hr and then cooled to room temperature and then added 3N-HC1 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-trifluoiOmethyl- pyrimidine (0.5g) as colorless crystalline solid, mp 196-200°C. Example 16: 5-Iodo-2-methylthio-4-(2-methyl-2H-tetrazol-5-yl)- 6- tri uoromethyl-pyrimidine
5-Iodo-2-methylthio-4-(2H-tetrazol-5-yl)-6-trifl.uoromethyl- pyrimidine (0.25g) was added benzene (4ml) and methanol (1ml). The mixture was added trimethylsilyldiazomethane (2M in hexane, 1ml) 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-(l-Chlorovinyl)-4-imidazol- l-yl-2-methyl-6-trifluoromethyl- pyrimidine:
4-Chloro-5-(l-chlorovinyl)-2-methyl-6-trifluoromethylpyrimidine (1.83g) was dissolved in acetonitrile (20ml) under stirring in room temperature. The mixture was added imidazole (1.45g) 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-(l-chlorovinyl)-4-imidazol-l-yl-2-methyl-6- trifluoromethyl-pyrimidine (1.34g) as pale brown oil. Η-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- l-yl-2-methyl-6-trifluoromethylpyrimidine: 5-(l-Chlorovinyl)-4-imidazol- l-yl-2-methyl-6-trifluoromethyl-pyrimidine (0.20g) was dissolved in dimethylsulfoxide (2ml) and l,8-diazabicyclo-[5,4,0]-undec-7-ene (O.llg) 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-l-yl- 2-methyl-6-trifluoromethylpyrimidine (O.llg) as colorless crystalline solid, mp 121- 122°C. Example 19: 5-Fluoro-2,4-diimidazol- l-yl-6-trifluoromethylpyrimidine: 2,4-Dichloro-5-fluoro-6-trifluoromethylpyrimidine (2.74g) was dissolved in acetonitrile (30ml) and imidazole (3.97g) 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-l-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 201 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 20t 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 V. 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 Vi 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
Figure imgf000026_0001
R1 R2 R3 Q mp (°C) SCH3 CF3 I 1,2,4-triazol-l-yl 93-94 SCH3 CF2CF3 I 1,2,4-triazol-l-yl SCH3 CF3 I 2H-tetrazol-5-yl 196-200 dec SCH3 CF2CF3 I 2H-tetrazol-5-yl SCH3 CF3 I 2-methyl-2H-tetrazol-5-yl 113-118 SCH3 CF2CF3 I 2-methyl-2H-tetrazol-5-yl SCH3 CF3 I 3-(p-acetoxybenzylthio)-l,2,4-triazol-l-yl SCH3 CF3 I 3-a ino-l,2,4-triazol-l-yl SCH3 CF3 I 3-bromo- 1, 2, 4-triazol- 1-yl SCH3 CF3 I 3-chloro- 1, 2, 4-triazol- 1-yl SCH3 CF3 I 3-cyano- 1,2, 4-triazol-l-yl SCH3 CF3 I 3-fluoro-l,2,4-triazol-l-yl SCH3 CF3 I 3-hydroxy-l,2,4-triazol-l-yl SCH3 CF3 I 3-mercapto- 1, 2, 4-triazol- 1-yl SCH3 CF3 I 3-rαethoxy-l,2,4-triazol- 1-yl SCH3 CF3 I 3-metb.ylamino- 1,2, 4-triazol- 1-yl SCH3 CF3 I 3-metb.yltbio- 1, 2, 4-triazol- 1-yl SCH3 CF3 I 3-trifluorometb.yl-l,2,4-triazol-l-yl SCH3 CF3 I 5-(p-acetoxybenzylthio)i idazol-l-yl SCH3 CF3 I 5-(p-acetoxybenzylthio)-l,2,4-triazol-l-yl 141-143 SCH3 CF3 I 4-aminoimidazol- 1-yl SCH3 CF3 I 5-amino- 1,2,4-triazol- 1-yl SCH3 CF3 I 4-brorαoimidazol- 1-yl 115-117 SCH3 CF3 I 5-bromo-l,2, 4-triazol- 1-yl SCH3 CF3 I 4-chloroimidazol- 1-yl 103-104 SCH3 CF3 I 5-chloro-l,2, 4-triazol- 1-yl SCH3 CF3 I 4-cyanoimidazol- 1-yl SCH3 CF3 I 5-cyano-l,2, 4-triazol-l-yl SCH3 CF3 I 4-£luoroimidazol- 1-yl SCH3 CF3 I 5-fluoro- 1, 2; 4-triazol- 1-yl SCH3 CF3 I 4-b.ydroxyimidazol- 1-yl SCH3 CF3 I 5-hydroxy- 1,2,4-triazol-l-yl SCH3 CF3 I 4-mercaptoimidazol- 1-yl SCH3 CF3 I 5-mercapto-l,2,4-triazol-l-yl SCH3 CF3 I 4-methoxyimidazol- 1-yl SCH3 GF3 I 5-rαethoxy-l,2,4-triazol-l-yl SCH3 CF3 I 4-methylaminoimidazol- 1-yl SCH3 CF3 I 5-methylamino- 1,2,4-triazol-l-yl SCH3 CF3 I 4- ethylimidazol- 1-yl 147-148 SCH3 CF2CF3 I 4-methylimidazol-l-yl SCH3 CF3 I 4-methylthioimidazol- 1-yl SCH3 CF3 I 5-methylthio-l,2,4-triazol-l-yl SCH3 CF3 I 4-trifluororαetb.ylimidazol- 1-yl SCH3 CF3 I 5-trifluoromethyl- 1,2,4-triazol-l-yl SCH3 CF3 I benzimidazol- 1-yl 128 SCH3 CF2CF3 I benzimidazol- 1-yl SCH3 CF3 I imidazol-1-yl 137-139 SCH3 CF CF3 I imidazol-1-yl 112-114 SCH3 CF3 I pyrazol-1-yl 115-116 SCH3 CF3 F 2H-tetrazol-5-yl SGH3 CF3 F 2-methyl-2H-tetrazol-5-yl SCH3 CF3 Cl 2H-tetrazol-5-yl 177-178 SCH3 CF3 Cl 2-methyl-2H-tetrazol-5-yl 128-130 SCH3 CF3 Br 1,2,4-triazol-l-yl 85-87 SCH3 CF3 Br 2H-tetrazol-5-yl 192-193 SCH3 CF3 Br 2-methyl-2H-tetrazol-5-yl 102-105 SCH3 CF3 Br imidazol-1-yl 89-90
SCΞI2CH3 CF3 I 1,2,4-triazol-l-yl
SCH2CH3 CF2CF3 I 1,2,4-triazol-l-yl
SCH2CH.3 GF3 I 2H-tetrazol-5-yl
SCH2C-H CF2CF3 I 2H-tetrazol-5-yl
SCH2CH3 CF3 I 2-methyl-2H-tetrazol-5-yl
SCH2CH.3 CF2CF3 I 2-methyl-2H-tetrazol-5-yl
SCH2CΪI3 CF3 I 4-methylimidazol- 1-yl
SCH2CIΪ3 CF2CF3 I 4-methylimidazol- 1-yl
SCH CJI3 CF3 I benzimidazol- 1-yl CF2CF3 I benzimidazol- 1-yl
SCΪ12C-E13 CF3 I imidazol-1-yl 106-109
SCΞΪ2CH3 CF2CF3 I imidazol-1-yl CF3 F 2H-tetrazol-5-yl
Figure imgf000027_0001
CF3 F 2-methyl-2H-tetrazol-5-yl
SCH2CIΪ3 CF3 Cl 2H-tetrazol-5-yl
SCH2CH3 CF3 Cl 2-methyl-2H-tetrazol-5-yl
SCH2CH3 CF3 Br 2H-tetrazol-5-yl
SCH2CH3 CF3 Br 2-methyl-2H-tetrazol-5-yl
SCH(CH3)2 CF3 I 1,2,3-triazol-l-yl 157-159
SCH(CH3)2 CF3 I l,2,3-triazol-2-yl 167-169
SCH(CH3)2 CF3 I 1,2,4-triazol-l-yl 70-71
SCH(CH3)2 CF2CF3 I 1,2,4-triazol-l-yl
SCH(CH3)2 CF3 I 2H-tetrazol-5-yl
SCH(CH3)2 CF2CF3 I 2H-tetrazol-5-yl
SCH(CH3)2 CF3 I 2-methyl-2H-tetrazol-5-yl
SCH(CH3)2 CF2CF3 I 2-methyl-2H-tetrazol-5-yl
SCH(CH3)2 CF3 I 2-methylimidazol- 1-yl 133-135
SCH(CH3)2 CF3 I 4-ethoxycarbonyl-3-triiluoromethylpyrazol-l-yl 107-108
SCH(CH3)2 CF3 I 4-methylimidazol- 1-yl 138-140
SCH(CH3)2 CF2CF3 I 4-methylimidazol- 1-yl
SCH(CH3)2 CF3 I benzimidazol- 1-yl 89 SCH(CH3)2 CF2CF3 I benzimidazol- 1-yl
90 SCH(CH3)2 CF3 I imidazol-1-yl 118-120
91 SCH(CH3)2 CF2CF3 I imidazol-1-yl
92 SCH(CH3)2 CF3 F 2H-tetrazol-5-yl
93 SCH(CH3)2 CF3 F 2-methyl-2H-tetrazol-5-yl
94 SCH(CH3)2 CF3 Cl 2H-tetrazol-5-yl
95 SCH(CH3)2 CF3 Cl 2-methyl-2H-tetrazol-5-yl
96 SCH(CH3)2 CF3 Br 2H-tetrazol-5-yl
97 SCH(CH3)2 CF3 Br 2-methyl-2H-tetrazol-5-yl
98 S(0)2CH3 CF3 I 1,2,4-triazol-l-yl
99 S(0)2CH3 CF2CF3 I 1,2,4-triazol-l-yl
100 S(0)2CH3 CF3 I 2H-tetrazol-5-yl
101 S(0)2CH3 CF2CF3 I 2H-tetrazol-5-yl
102 S(0)2CH3 CF3 I 2-methyl-2H-tetrazol-5-yl
103 S(0)2CH3 CF2CF3 I 2-methyl-2H-tetrazol-5-yl
104 S(0)2CH3 CF3 I 4-methylimidazol- 1-yl
105 S(0)2CH3 CF2CF3 I 4-methylimidazol- 1-yl
106 S(0)2CH3 CF3 I benzimidazol- 1-yl
107 S(0)2CH3 CF2CF3 I benzimidazol- 1-yl
108 S(0)2CH3 CF3 I _f*»- imidazol-1-yl
109 S(0)2CH3 CF2CF3 I imidazol-1-yl
110 S(0)2CH3 CF3 F 2H-tetrazol-5-yl
111 S(0)2CH3 CF3 F 2-methyl-2H-tetrazol-5-yl
112 S(0)2CH3 CF3 Cl 2H-tetr azol- 5 -yl
113 S(0)2CH3 CF3 Cl 2-methyl-2H-tetrazol-5-yl
114 S(0)2CH3 CF3 Br 1,2,4-triazol-l-yl 158-159
115 S(0)2CH3 CF3 Br 2H-tetrazol-5-yl
116 S(0)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-l-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-l-yl 169-171 136 pyridin-2-yl CF2CF3 I 1,2,4-triazol-l-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-l-yl
157 pyrazol-1-yl CF2CF3 I 1,2,4-triazol-l-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-l-yl
175 phenyl CF2CF3 I 1,2,4-triazol-l-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-methyUmidazol- 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 CF CF3 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-l-yl
193 OCH3 CF2CFg I 1,2,4-triazol-l-yl
194 OCH3 CFg 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-l-yl
199 OCH3 CF3 I 3-amino-l,2, 4-triazol- 1-yl
200 OCH3 CF3 I 3-brorαo- 1, 2,4-triazol- 1-yl
201 OCH3 CF3 I 3-chloro-l,2,4-triazol-l-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-l,2,4-triazol-l-yl
206 OCH3 CF3 I 3-methoxy-l, 2,4-triazol- 1-yl
207 OCH3 CFg I 3-methylamino-l, 2,4-triazol- 1-yl
208 OCH3 CF3 I 3-methylthio- 1,2,4-triazol-l-yl
209 OCHg CF3 I 3-trifluoromethyl- 1,2,4-triazol- 1-yl
210 OCHg CF3 I 5-(p-acetoxybenzylthio)imidazol-l-yl
211 OCHg CF3 I 5-(p-acetoxybenzylthio)-l,2, 4-triazol- 1-yl
212 OCHg CF3 I 4-aminoimidazol- 1-yl
213 OCH3 CF3 I 5-amino- 1,2,4-triazol-l-yl
214 OCH3 CF3 I 4-bromoimidazol- 1-yl
215 OCH3 CF3 I 5-bromo- 1,2,4-triazol-l-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 OCHg CF3 I 5-cyano- 1,2,4-triazol- 1-yl
220 OCHg CF3 I 4-fluoroimidazol- 1-yl
221 OCHg 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 CFg I 4-mercaptoimidazol- 1-yl 225 OCH3 CFg I 5-mercapto-l,2,4-triazol-l-yl 226 OCH3 CFg I 4-methoxyimidazol- 1-yl 227 OCH3 CFg I 5-methoxy- 1,2,4-triazol- 1-yl 228 OCH3 CFg I 4-methylaminoimidazol- 1-yl 229 OCH3 CFg 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 OCHg CF3 I 4-methylthioimidazol-l-yl
233 OCHg CF3 I 5-methylthio- 1,2,4-triazol-l-yl
234 OCHg 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 CF CF3 I benzimidazol- 1-yl
238 OCHg 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 OCHg 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 OCHg CF3 Br 2-methyl-2H-tetrazol-5-yl
246 OCBjC≡CH CF3 I 1,2,4-triazol- 1-yl
247 OCH2C≡CH CF2CF3 I 1,2,4-triazol-l-yl
248 OCH2G≡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 CFg F 2H-tetrazol-5-yl
259 OCH2C≡CH CFg F 2-methyl-2H-tetrazol-5-yl
260 OCH2C--CH CFg 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-l-yl
265 OCH2CII3 CF2CF3 I 1,2,4-triazol-l-yl
266 OC-H.2CH3 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 OCXI2CII3 CF2CF3 I 4-methyl i τrι idazol- 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 CFg 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 0 CH2 CH2 CH CF3 I 1,2,4-triazol-l-yl
283 OCH2CH2CH3 CF2CF3 I 1,2,4-triazol-l-yl
284 0 CH2 CH.2 CH-3 CF3 I 2H-tetrazol-5-yl
285 0 CH2 CH.2 CH.3 CF2CF3 I 2H-tetrazol-5-yl
286 0 CH-2 CH2 CH3 CF3 I 2-methyl-2H-tetrazol-5-yl
287 0 CH.2 CH2 CH CF2CF3 I 2-methyl-2H-tetrazol-5-yl
288 0 CH2 CH2 CH3 CF3 I 4-methylimidazol- 1-yl
289 0 CH2 CH2 CH3 CF2CF3 I 4-methylimidazol- 1-yl
290 0 CH2 CH2 CH3 CF3 I benzimidazol- 1-yl
291 OCH2CH2CH3 CF2CF3 I benzimidazol- 1-yl
292 OCH2CH2 H3 CF3 I imidazol-1-yl 84-86
293 OCH CH2 H3 CF2CF3 I imidazol-1-yl
294 OCH2CH2CH3 CF3 F 2H-tetrazol-5-yl
295 OCH2CH2CH3 CF3 F 2-methyl-2H-tetrazol-5-yl
296 0 CH2 CH2 CH-3 CFg Cl 2H-tetrazol-5-yl
297 0 CH2 CH2 CH.3 CFg Cl 2-methyl-2H-tetrazol-5-yl
298 0 CH2 CH2 CH3 CF3 Br 2H-tetrazol-5-yl
299 0 CH2 CH2 CH-3 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-l-yl
302 OCH CF2H 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 CF2CFg I benzimidazol- 1-yl
310 OCH2CF2H CFg I imidazol-1-yl 97-98 311 OCH2CF2H CF2CFg I imidazol-1-yl 312 OCH2CF2H CF3 F 2H-tetr azol- 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-l-yl 319 OCH(CH3)2 CF2CF3 I 1,2,4-triazol-l-yl 320 OCH(CH3)2 CF3 I 2H-tetrazol-5-yl 321 OCH(CH3)2 CF2GF3 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 CFg F 2H-tetrazol-5-yl
331 OCH(CH3)2 CFg F 2-methyl-2H-tetrazol-5-yl
332 OCH(CH3)2 CFg Cl 2H-tetrazol-5-yl
333 OCH(CH3)2 CFg Cl 2-methyl-2H-tetrazol-5-yl
334 OCH(CH3)2 CFg Br 2H-tetrazol-5-yl
335 OCH(CH3)2 CFg Br 2-methyl-2H-tetrazol- 5 -yl
336 imidazol-1-yl CF3 I 1,2,4-triazol-l-yl
337 imidazol-1-yl CF2CF3 I 1,2,4-triazol-l-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 CF2CFg I benzimidazol- 1-yl
346 imidazol-1-yl CFg I imidazol- 1-yl > 160 dec
347 imidazol-1-yl CF2CFg I imidazol- 1-yl
348 imidazol-1-yl CFg 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-l-yl 115-116
356 H CF2CF3 I 1,2,4-triazol-l-yl 83-84
357 H CF3 I 2H-tetrazol-5-yl 191-194
358 H CF2CF3 I 2H-tetrazol-5-yl
359 H CFg 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-arαino- 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-l-yl 365 H CF3 I 3-cyano- 1,2,4-triazol-l-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-l-yl 369 H CF3 I 3-methoxy-l, 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-trifl.uoromethyl- 1,2,4-triazol- 1-yl
373 H CF3 I 5-(p-acetoxybenzylthio)imidazol-l-yl
374 H CF3 I 5-(p-acetoxybenzylthio)-l,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-l-yl 138-140
378 H CF3 I 5-bromo- 1, 2,4-triazol- 1-yl
379 H CF3 I 4-chloroimidazol-l-yl 123-124
380 H CF3 I 5-chloro-l,2,4-triazol-l-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-l,2,4-triazol-l-yl
389 H CF3 I 4-methoxyimidazol- 1-yl
390 H CF3 I 5-methoxy-l,2,4-triazol-l-yl
391 H CF3 I 4-methylaminoimidazol- 1-yl
392 H CF3 I 5-methylamino-l,2,4-triazol-l-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-l-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 CFg 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 CFg I 1,2,4-triazol-l-yl
410 C≡CSi(CHg)g CF2CFg I 1,2,4-triazol-l-yl
411 C≡CSi(CH3)g CF3 I 2H-tetrazol-5-yl
412 C≡CSi(CH3)3 CF2CF3 I 2H-tetrazol-5-yl
413 C-.CSi(CHg)3 CF3 I 2-methyl-2H-tetrazol- 5 -yl
414 C≡CSi(CH3)g 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(CHg)g CFg F 2-methyl-2H-tetrazol-5-yl
423 C≡CSi(CHg)g CFg Cl 2H-tetrazol-5-yl
424 C≡CSi(CH3)3 CFg Cl 2-methyl-2H-tetrazol-5-yl
425 C≡CSi(CH3)3 CFg Br 2H-tetrazol-5-yl
426 C≡CSi(CH3)3 CFg Br 2-methyl-2H-tetrazol-5-yl
427 CH3 CF3 vinyl imidazol- 1-yl oil
428 CH3 CF3 1,2,4-triazol-l-yl 119-121
429 CH3 CF2CF3 1,2,4-triazol-l-yl
430 CH3 CF3 2H-tetrazol-5-yl 180-182
431 CH3 CF2CFg 2H-tetrazol-5-yl
432 CH3 CF3 2-methyl-2H-tetrazol-5-yl 131-133
433 CH3 CF2CF3 , 2-methyl-2H-tetrazol-5-yl
434 CH3 CF3 3-(p-acetόxybenzylthio)- 1,2,4-triazol-l-yl
435 CH3 CF3 3-amino-l,2,4-triazol-l-yl
436 CH3 CF3 3-bromo- 1,2,4-triazol-l-yl
437 CH3 CF3 3-chloro- 1,2,4-triazol-l-yl
438 CH3 CF3 3-cyano- 1,2,4-triazol- 1-yl
439 CH3 CFg 3 -fluor o- 1,2, 4-triazol- 1 -yl
440 CH3 CFg 3-hydroxy-l,2, 4-triazol- 1-yl
441 CH3 CF3 3-mercapto- 1,2,4-triazol-l-yl
442 CH3 CF3 3-methoxy-l, 2,4-triazol- 1-yl
443 CH3 CF3 3-methylamino-l,2,4-triazol-l-yl
444 CH3 CF3 3-methylthio-l, 2,4-triazol- 1-yl
445 CH3 CF3 3-trifluoromethyl- 1,2,4-triazol- 1-yl
446 CH3 CF3 5-(p-acetoxybenzylthio)irαidazol-l-yl
447 CH3 CF3 5-(p-acetoxybenzylthio)-l,2,4-triazol-l-yl
448 CH3 CF3 4-aminoimidazol- 1-yl
449 CH3 CF3 5-amino- 1,2,4-triazol-l-yl
450 CH3 CFg 4-bromoimidazol-l-yl 80-85
451 CH3 CFg 5-bromo- 1,2,4-triazol-l-yl
452 . CH3 CFg 4-chloroimidazol- 1-yl
453 CH3 CF3 5-chloro- 1,2,4-triazol- 1-yl
454 CH3 CF3 4-cyanoimidazol- 1-yl
455 CH3 CF3 5-cyano- 1,2,4-triazol-l-yl
456 CH3 CF3 4-fluoroimidazol-l-yl
457 CH3 CF3 5-fluoro- 1,2,4-triazol-l-yl
458 CH3 CF3 4-hydroxyimidazol- 1-yl
459 CH3 CFg 5 -hydroxy- 1 , 2, 4-triazol- 1-yl 460 CH3 CFg 4-mercaptoimidazol- 1-yl 461 CH3 CF3 5-mercapto- 1,2, 4-triazol- 1-yl 462 CH3 CF3 4-methoxyimidazol- l:yl 463 CH3 CF3 5-methoxy-l,2,4-triazol-l-yl 464 CHg CF3 4-methylaminoimidazol- 1-yl 465 CH3 CF3 I 5-methylamino- 1,2, 4-triazol-l-yl
466 CH3 CF3 I 4-methylimidazol- 1-yl 155-156
467 CH3 CF CF3 I 4-methylimidazol- 1-yl
468 CH3 CF3 I 4-methylthioimidazol- 1-yl
469 CH3 CF3 I 5-methylthio- 1, 2, 4-triazol-l-yl
470 CH3 CF3 I 4-trifluoromethylimidazol- 1-yl
471 CH3 CF3 I 5-trifluoromethyl- 1,2,4-triazol-l-yl
472 CHg CF3 I benzimidazol-1-yl
473 CHg CF2CFg 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 1,2,4-triazol-l-yl 50-51
486 CH2CH3 CF2CFg 1,2,4-triazol-l-yl
487 CH2CHg CFg 2H-tetrazol-5-yl 165-167
488 CH2CHg CF2CF3 2H-tetrazol-5-yl
489 CH2CHg CF3 2-methyl-2H-tetrazol-5-yl 112-113
490 CH2CHg CF2CF3 2-methyl-2H-tetrazol-5-yl
491 CH2CH3 CF3 3-(p-acetoxybenzylthio)- 1,2,4-triazol- 1-yl
492 CH CH3 CF3 3-amino- 1,2,4-triazol-l-yl
493 CH2CH3 CFg 3-bromo- 1,2,4-triazol-l-yl
494 CH2CH3 CFg 3-chloro- 1, 2, 4-triazol- 1-yl
495 CH2CH3 CF3 3-cyano- 1,2,4-triazol- 1-yl
496 CH2CH3 CF3 3-fluoro-l,2,4-triazol-l-yl
497 CH2CH3 CF3 3-hydroxy-l,2,4-triazol-l-yl
498 CH2CH3 CF3 3-mercapto-l,2,4-triazol-l-yl
499 CH CH3 CF3 3-methoxy- 1,2, 4-triazol- 1-yl
500 CH2CH3 CF3 3-methylamino- 1,2, 4-triazol- 1-yl 501 CH2CH3 CFg 3-methylthio- 1,2,4-triazol- 1-yl 502 CH2CH3 CFg 3-trifl.uoromethyl- 1, 2, 4-triazol- 1-yl 503 CH2CH3 CF3 5-(p-acetoxybenzylthio)imidazol-l-yl 504 CH2CH3 CF3 5-(p-acetoxybenzylthio)- 1,2,4-triazol-l-yl 505 CH2CH3 CFg 4-aminoimidazol- 1-yl 506 CH2CHg CF3 5-amino- 1,2, 4-triazol-l-yl 507 CH2CH3 CF3 4-bromoimidazol- 1-yl 508 CH2CH3 CF3 5-bromo- 1,2,4-triazol-l-yl 509 CH2CH3 CF3 4-chloroimidazol- 1-yl 510 CH2CH3 CFg 5-chloro-l,2,4-triazol-l-yl 511 CH2CH3 CFg 4-cyanoimidazol- 1-yl 512 CH2CH3 CF3 I 5-cyano-l,2, 4-triazol- 1-yl
513 CH2CH3 CFg I 4-fluoroimidazol- 1-yl
514 CH2CH3 CFg I 5-fl.uoro-l,2, 4-triazol-l-yl
515 CH2CH3 CFg I 4-hydroxyimidazol- 1-yl
516 CH2CH3 CFg I 5-hydroxy- 1,2,4-triazol-l-yl
517 CH2CH3 CFg I 4-mercaptoimidazol- 1-yl
518 CH2CH3 CFg 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 CH2CHg CF3 I 4-methylaminoimidazol- 1-yl
522 CH2CHg CF3 I 5-methylamino- 1,2,4-triazol-l-yl
523 CH2CH3 CF3 I 4-methylimidazol- 1-yl 110-111
524 CH2CH3 CF2CF3 I 4-methylimidazol- 1-yl
525 CH2CH3 CF3 I 4-methylthioimidazol- 1-yl
526 CH2CH3 CF3 I 5-methylthio- 1,2,4-triazol- 1-yl
527 CH2CH3 CF3 I 4-trifhιoromethylimidazol- 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 CF2CFg 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-rαethyl-2H-tetrazol-5-yl
537 CH CH3 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-l-yl
540 6-phenylpyridin -2-yl CF2CFg I 1,2,4-triazol-l-yl
541 6-phenylpyridin-2-yl CFg 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 CF CF3 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-l-yl 559 6-methylpyridin-2-yl CF2CF3 I 1,2,4-triazol-l-yl
560 6-methylpyridin-2-yl CFg 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 CF2CFg 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 CFg Br 2-methyl-2H-tetrazol-5-yl
576 2-oxopyrroUdin- 1-yl CF3 I 1,2,4-triazol-l-yl
577 2-oxopyrrolidin- 1-yl CF2CF3 I 1,2,4-triazol-l-yl
578 2-oxopyrrolidin- 1-yl CF3 I 2H-tetrazol-5-yl
579 2-oxopyrroHdin-l-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-l-yl CF3 I 4-methylimidazol- 1-yl
583 2-oxopyrrolidin- 1-yl CF2CF3 I 4-methylimidazol- 1-yl
584 2-oxopyrrolidin-l-yl CF3 I benzimidazol-1-yl
585 2-oxopyrrolidin-l-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-oxopyrroUdin- 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-l-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- lH-tetrazol-5-yl 110-112
595 SCH-3 CF3 I 1-methyl- lH-tetrazol-5-yl
596 SCH2CH3 CF3 I 1-methyl- lH-tetrazol-5-yl
597 OCHg CF3 I 1-methyl- lH-tetrazol-5-yl
598 OCH2CH3 CF3 I 1-methyl- lH-tetrazol-5-yl
599 H CF3 I 1-methyl- lH-tetrazol-5-yl 117-119
600 CH2CHg CF3 I 1-methyl- lH-tetrazol-5-yl 96-97
601 phenyl CF3 I 1-methyl- lH-tetrazol-5-yl
602 imidazol- 1-yl CF3 I 1-methyl- lH-tetrazol-5-yl
603 pyridin-2-yl CFg I 1-methyl- lH-tetrazol-5-yl
604 pyridin-3-yl CFg I 1-methyl- lH-tetrazol-5-yl
605 pyridin-4-yl CF3 I 1-methyl- lH-tetrazol-5-yl 606 CH3 CF3 Br 1-methyl- lH-tetrazol-5-yl
607 SCH3 CF3 Br 1-methyl- lH-tetrazol-5-yl
608 SCH2CH3 CF3 Br 1-methyl- lH-tetrazol-5-yl
609 OCH3 CF3 Br 1 -methyl- lH-tetr azol- 5-yl
610 OCH2CH3 CF3 Br 1-methyl- lH-tetrazol-5-yl
611 H CF3 Br 1-methyl- lH-tetrazol-5-yl
612 CH2CH3 CF3 Br 1-methyl- lH-tetrazol-5-yl
613 phenyl CFg Br 1-methyl- lH-tetrazol-5-yl
614 imidazol- 1-yl CFg Br 1-methyl- lH-tetrazol-5-yl
615 pyridin-2-yl CFg Br 1-methyl- lH-tetrazol-5-yl
616 pyridin-3-yl CFg Br 1-methyl- lH-tetrazol-5-yl
617 pyridin-4-yl CF3 v 1-methyl- lH-tetrazol-5-yl
618 CHg CF3 Cl 1-methyl- lH-tetrazol-5-yl
619 SCH3 CF3 Cl 1-methyl- lH-tetrazol-5-yl
620 SCH2CH3 CF3 Cl 1-methyl- lH-tetrazol-5-yl
621 OCH3 CF3 Cl 1-methyl- lH-tetrazol-5-yl
622 OCH2CH3 CF3 Cl 1-methyl- lH-tetrazol-5-yl
623 H CF3 Cl 1-methyl- lH-tetrazol-5-yl
624 CH2CH3 CFg Cl 1-methyl- lH-tetrazol-5-yl
625 phenyl CFg Cl 1-methyl- lH-tetrazol-5-yl
626 imidazol- 1-yl CFg Cl 1-methyl- lH-tetrazol- 5 -yl
627 pyridin-2-yl CFg Cl 1 -methyl- lH-tetrazol- 5-yl
628 pyridin-3-yl CF3 Cl 1 -methyl- lH-tetr azol- 5-yl
629 pyridin-4-yl CF3 Cl 1-methyl- lH-tetrazol-5-yl
630 CHg CF3 F 1-methyl- lH-tetrazol-5-yl
631 SCHg CF3 F 1-methyl- lH-tetrazol-5-yl
632 SCH2CH.3 CF3 F 1-methyl- lH-tetrazol-5-yl
633 OCHg CF3 F 1-methyl- lH-tetrazol-5-yl
634 OCH2CH3 CF3 F 1-methyl- lH-tetrazol-5-yl
635 H CF3 F 1-methyl- lH-tetrazol-5-yl
636 CH CH3 CF3 F l-methyl-lH-tetrazol-5-yl
637 phenyl CF3 F 1-methyl- lH-tetrazol-5-yl
638 imidazol- 1-yl CF3 F 1-methyl- lH-tetrazol-5-yl
639 pyridin-2-yl CF3 F 1-methyl- lH-tetrazol-5-yl
640 pyridin-3-yl CF3 F 1-methyl- lH-tetrazol-5-yl
641 pyridin-4-yl CF3 F 1-methyl- lH-tetrazol-5-yl
642 SCH2F CF3 imidazo .1-1-yl
643 SCH2C1 CF3 imidazo ιl-1-yl
644 SCF3 CF3 imidazo 1' -1-yl
645 S(0)CH3 CF3 imidazo '1-ι-yi
646 S(0)CF3 CF3 imidazo 1-1-yl
647 S(0)2CF3 CF3 imidazo 1-1-yl
648 6-phenylpyridin-4-yl CF3 imidazo 1-1-yl
649 6-methylpyridin-4-yl CF3 imidazo 'i-i-yi
650 6-chloropyridin-4-yl CF3 imidazo '1-1-yl
651 '. -trifluoromethylpyridin-4-y CF3 imidazo 'i-i-yi
652 6-phenylpyridin-3-yl CF3 imidazo '1-1-yl 653 6-methylpyridin-3-yl CF3 I imidazol- 1-yl
654 6-chloropyridin-3-yl CF3 I imidazol- 1-yl
655 3 -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 -trifl.uoromethylpyridin-2-y CF3 I imidazol- 1-yl
659 3-methylpyrazol- 1-yl CF3 I imidazol- 1-yl
660 3-methoxypyrazol-l-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 CFg I imidazol- 1-yl
672 3-(trifluoromethyl)phenyl CFg I imidazol- 1-yl
673 4-(trifluoromethyl)phenyl CFg I imidazol- 1-yl
674 OCH2CF3 CFg I imidazol-1-yl
675 0CH2C≡CCH2C1 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≡CCH2C1 CF3 I imidazol- 1-yl
681 CF3 CF3 I 1,2,4-triazol-l-yl 137-138
682 CF3 CF2CF3 I 1,2,4-triazol-l-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 CFg I 4-methylimidazol- 1-yl
688 CF3 CF2CF3 I 4-methylimidazol- 1-yl
689 CF3 CF3 I benzimidazol- 1-yl
690 CFg CF2CF3 I benzimidazol- 1-yl
691 CF3 CF2CF3 I imidazol- 1-yl
692 CF3 CFg I imidazol- 1-yl 105-106
693 CF3 CFg F 2H-tetrazol-5-yl
694 CF3 CFg 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=CHCH2C1 CF3 I imidazol- 1-yl 700 SCH3 CFg I 4, 5-dichloroimidazol- 1-yl 114-115
701 SCH3 CF2CF3 I 4,5-dichloroimidazol-l-yl
702 SCH3 CF3 I 3-methyl- 1,2, 4-triazol- 1-yl 84-85
703 SCHg CF2CF3 I 3-methyl- 1,2, 4-triazol- 1-yl
704 SCH3 CF3 I 3-methyl- l,2,4-triazol-2-yl 150-151
705 SCH3 CF2CF3 I 3-methyl- l,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- lH-tetrazol-5-yl
709 SCH3 CF2CF3 I l-ethyl-lH-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- lH-tetrazol-5-yl
713 SCH3 CF2CF3 I 1-isopropyl- lH-tetrazol- 5 -yl
714 SCH3 CF3 I 2-prop argyl-2H-tetrazol-5-yl
715 SCHg CF2CF3 I 2-propargyl-2H-tetrazol-5-yl
716 SCHg CF3 I 1-propargyl- lH-tetrazol-5-yl
717 SCHg CF2CF3 I 1-propargyl- lH-tetrazol-5-yl
718 SCHg CF3 I 4, 5-dimethylimidazol- 1-yl 168-170
719 SCH3 CF2CF3 I 4, 5-dimethylimidazol- 1-yl
720 SCHg CF3 I 4, 5-dibromoimidazol- 1-yl 118-120
721 SCHg CF2CF3 I 4, 5-dibromoimidazol- 1-yl
722 SCHg CF3 I 4-trifluoromethylimidazol- 1-yl 90-92
723 SCHg CF2CF3 I 4-trifluoromethyl i m idazol- 1-yl
724 SCHg CF3 I 4-cyanoimidazol- 1-yl 147-149
725 SCH3 CF2CF3 I 4-cyanoimidazol- 1-yl
726 SCHg CF3 I 4, 5-diiodoimidazol- 1-yl 157-160
727 SCHg CF2CFg I 4, 5-diiodoimidazol- 1-yl
728 SCH2CH.3 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-l,2, 4-triazol-l-yl
732 SCH2CH3 CF3 I 3-methyl- l,2,4-triazol-2-yl
733 SCH2CH3 CF2CF3 I 3-methyl- l,2,4-triazol-2-yl
734 SCH2CH.3 CF3 I 2-ethyl-2H-tetrazol-5-yl
735 SCΗ.2CH3 CF2CFg I 2-ethyl-2H-tetrazol-5-yl
736 SCH2CH3 CF3 I 1-ethyl- lH-tetrazol-5-yl
737 SCH2CH3 CF2CF3 I 1-ethyl- lH-tetrazol-5-yl
738 SCH2CH.3 CF3 I 2-isopropyl-2H-tetrazol-5-yl 739 SCH2CH3 CF2CF3 I 2-isopropyl-2H-tetrazol-5-yl 740 SCH2CH3 CF3 I 1-isopropyl- lH-tetr azol- 5-yl 741 SCH2CH3 CF2CF3 I 1-isopropyl- lH-tetrazol-5-yl 742 SCH2CH3 CF3 I 2-prop ar gyl-2H-tetrazol- 5 -yl 743 SCH2CH3 CF2CF3 I 2-prop ar gyl- 2H-tetrazol- 5 -yl 744 SCH2CH3 CF3 I 1-propargyl- lH-tetrazol-5-yl 745 SCH2CH.3 CF2CF3 I 1-propargyl- lH-tetrazol-5-yl 746 SCH2CH3 CF3 I 4, 5-dimethylimidazol- 1-yl 747 SCH2CH3 CF2CF3 I 4, 5-dimethylimidazol- 1-yl
748 SCH CH3 CFg I 4, 5-dibromoimidazol- 1-yl
749 SCH2CH3 CF2CF3 I 4, 5-dibromoimidazol- 1 -yl
750 SCH2CH CF3 I 4-trifluoromethylimidazol- 1-yl
751 SCH2CH3 CF2CF3 I 4-trifluoromethylimidazol- 1-yl
752 SCH2CHg CFg I 4-cyanoimidazol- 1-yl
753 SCH2CH3 CF2CF3 I 4-cyanoimidazol- 1-yl
754 SCH CH3 CFg I 4, 5-diiodoimidazol- 1-yl
755 SCH CH3 CF2CF3 I 4, 5-diiodoimidazol- 1-yl
756 SCH(CH3)2 CFg I 4,5-dichloroimidazol-l-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- lH-tetrazol-5-yl
765 SCH(CH3)2 CF2CF3 I 1-ethyl- lH-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- lH-tetrazol-5-yl
769 SCH(CH3)2 CF2CF3 I 1-isopropyl- lH-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- lH-tetrazol-5-yl
773 SCH(CH3)2 CF2CF3 I 1-propargyl- lH-tetrazol-5-yl
774 SCH(CH3)2 CF3 I 4, 5-dimethylimidazol- 1-yl
775 SCH(CH3)2 CF2CF3 I 4,5-dimethylimidazol-l-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 CF2CFg 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-l,2,4-triazol-l-yl 787 pyridin-2-yl CF2CFg I , 3 -methyl- 1, 2, 4-triazol- 1-yl 788 pyridin-2-yl CFg I 3-methyl- 1,2, 4-triazol-2-yl 789 pyridin-2-yl CF2CF3 I 3-methyl-l,2,4-triazol-2-yl 790 pyridin-2-yl CFg I 2-ethyl-2H-tetrazol-5-yl 791 pyridin-2-yl CF CF3 I 2-ethyl-2H-tetrazol-5-yl 792 pyridin-2-yl CF3 I 1-ethyl- lH-tetrazol-5-yl 793 pyridin-2-yl CF2CF3 I 1-ethyl- lH-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- lH-tetrazol-5-yl
797 pyridin-2-yl CF2CF3 I 1-isopropyl- lH-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- lH-tetrazol-5-yl
801 pyridin-2-yl CF2CF3 I 1-propargyl- lH-tetrazol-5-yl
802 pyridin-2-yl CF3 I 4,5-dimethyKmidazol-l-yl
803 pyridin-2-yl CF2CF3 I 4,5-dimethyUmidazol-l-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-trifluoromethyHmidazol- 1-yl
807 pyridin-2-yl CF2CF3 I 4-trifluoromethylimidazol- 1-yl
808 pyridrn-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-l-yl
815 phenyl CF2 F I 3-methyl- 1,2,4-triazol-l-yl
816 phenyl CF3 I 3-methyl-l,2,4-triazol-2-yl
817 phenyl CF2CF3 I 3-methyl-l,2,4-triazol-2-yl
818 phenyl CF3 I , 2-ethyl-2H-tetrazol-5-yl
819 phenyl CF2 F I 2-ethyl-2H-tetrazol-5-yl
820 phenyl CF3 I 1-ethyl- lH-tetrazol-5-yl
821 phenyl CF2CF3 I 1-ethyl- lH-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- lH-tetrazol-5-yl
825 phenyl CF2CF3 I 1-isopropyl- lH-tetrazol-5-yl
826 phenyl CFg I 2-propargyl-2H-tetrazol-5-yl
827 phenyl CF2CF3 I 2-propargyl-2H-tetrazol-5-yl
828 phenyl CF3 I 1-propargyl- lH-tetrazol-5-yl
829 phenyl CF CF3 I 1-propargyl- lH-tetr azol- 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-l-yl 833 phenyl CF2CF3 I 4, 5-dibromoimidazol- 1-yl 834 phenyl CF3 . I 4-trifluoromethylimidazol- 1-yl 835 phenyl CF2CF3 I 4-trifluoromethyUmidazol- 1-yl 836 phenyl CFg I 4-cyanoimidazol- 1-yl 837 phenyl CF2CF 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-l-yl 841 OCHg CF2CF3 I 4,5-dichloroimidazol-l-yl
842 OCH3 CF3 I 3-methyl-l,2,4-triazol-l-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-l,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- lH-tetrazol-5-yl
849 OCHg CF2CF3 I 1-ethyl- lH-tetrazol-5-yl
850 OCHg CF3 I 2-isopropyl-2H-tetrazol-5-yl
851 OCHg CF2CF3 I 2-isopropyl-2H-tetrazol-5-yl
852 OCHg CF3 I 1-isopropyl- lH-tetrazol-5-yl
853 OCH3 CF2CF3 I 1-isopropyl- lH-tetrazol-5-yl
854 OCH3 CFg I 2-propargyl-2H-tetrazol-5-yl
855 OCH3 CF2CF3 I 2-propargyl-2H-tetrazol-5-yl
856 OCH3 CFg I 1-propargyl- lH-tetrazol-5-yl
857 OCH3 CF2CFg I 1-propargyl- lH-tetrazol-5-yl
858 OCH3 CFg I 4, 5-dimethylimidazol- 1-yl
859 OCH3 CF2CF3 I 4, 5-dimethyKmidazol- 1-yl
860 OCHg CF3 I 4,5-dibromoimidazol-l-yl
861 OCH3 CF2CF3 I 4,5-dibromoimidazol-l-yl
862 OCH3 CF3 I 4-trifluoromethylimidazol- 1-yl
863 OCHg CF2CF3 I 4-trifluoromethylimidazol- 1-yl
864 OCH3 CF3 I 4-cyanoimidazol- 1-yl
865 OCH3 CF CF3 I 4-cyanoimidazol- 1-yl
866 OCH3 CF3 I 4,5-diiodoimidazol-l-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- l,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 CFg I 1-ethyl- lH-tetrazol-5-yl 877 OCHzC≡CH CF2CFg I 1-ethyl- lH-tetrazol-5-yl 878 OCH2C≡CH CF8 " I 2-isopropyl-2H-tetrazol-5-yl 879 OCH2C≡CH CF2CFg I 2-isopropyl-2H-tetrazol-5-yl 880 OCH2C--CH CF3 I 1-isopropyl- lH-tetrazol-5-yl 881 OCH2C≡CH CF2CF3 I 1-isopropyl- lH-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 CFg I 1-propargyl- lH-tetrazol-5-yl 885 OCH2C≡CH CF2CFg I 1-propargyl- lH-tetrazol-5-yl 886 OCH2C≡CH CFg I 4, 5-dimethylimidazol- 1 -yl 887 OCH2C≡CH CF2CFg I 4,5-dimethylimidazol-l-yl 888 OCH2CsCH CFg I 4, 5-dibromoimidazol- 1-yl
889 OCH2C≡CH CF2CF3 I 4,5-dibromoimidazol-l-yl
890 OCH2C≡CH CF3 I 4-trifluoromethylimidazol- 1-yl
891 OCH2CsCH 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-dϋodoimidazol-l-yl
895 OCH2C≡CH CF2CF3 ] 4,5-dnodoimidazol-l-yl
896 OCH2CH3 CF3 1 4,5-dichloroimidazol-l-yl
897 OCH2CH3 CF2CF3 I 4, 5-dichloroimidazol- 1-yl
898 OCH CH3 CF3 I 3-methyl- 1,2,4-triazol-l-yl
899 OCH CH3 CF2CF3 I 3-methyl-l,2,4-triazol-l-yl
900 OCH2CH3 CFg 1 3-methyl- l,2,4-triazol-2-yl
901 OCH2CH3 CF2CF3 ] 3-methyl-l,2,4-triazol-2-yl
902 OCH2CH3 CF3 I 2-ethyl-2H-tetrazol-5-yl
903 OCH2CH3 CF2CF3 ; 2-ethyl-2H-tetrazol-5-yl
904 OCH2CH3 CF3 ] 1-ethyl- lH-tetrazol-5-yl
905 OCH2CH3 CF2CF3 j 1-ethyl- lH-tetrazol-5-yl
906 OCH2CH3 CF3 ] 2-isopropyl-2H-tetrazol-5-yl
907 OCH2CH3 CF2CF3 2-isopropyl-2H-tetrazol-5-yl
908 OCH2CH3 CF3 ] 1-isopropyl- lH-tetrazol-5-yl
909 OCH2CH3 CF2CF3 1-isopropyl- lH-tetrazol-5-yl
910 OCH2CH3 CF3 ] 2-propargyl-2H-tetrazol-5-yl
911 OCH2CH3 CF2CF3 2-prop ar yl-2H-tetrazol- 5 -yl
912 OCH2CH3 CF3 ] 1-propargyl- lH-tetrazol-5-yl
913 OCH2CH3 CF2CF3 1-propargyl- lH-tetrazol-5-yl
914 OCH2CH3 CF3 ] 4, 5-dimethyHmidazol- 1-yl
915 OCH2CH3 CF2CF3 4, 5-dimethylimidazol- 1-yl
916 OCH2CH3 CF3 ] 4,5-dibromoimidazol-l-yl
917 OCH2CH3 CF2CF3 4,5-dibromoimidazol-l-yl
918 OCH2CH3 CFg ] 4-trifluoromethyHmidazol- 1-yl
919 OCH2CH3 CF2CFg 4-trifluoromethyHmidazol- 1-yl
920 OCH2CH3 CFg ] 4-cyanoimidazol- 1-yl
921 OCH2CH3 CF2CF3 ] 4-cyanoimidazol- 1-yl
922 OCH CH3 CF3 4,5-dnodoimidazol-l-yl
923 OCH2CH3 CF2CF3 4, 5-diiodoimidazol- 1-yl
924 OCH2CH CH3 CFg 4,5-dichloroimidazol-l-yl
925 OCH2CH2CH3 CF2CF3 4,5-dichloroimidazol-l-yl
926 OCH2CH2CH3 CF3 [ 3-methyl-l,2,4-triazol-l-yl
927 OCH2CH CHg CF2CF3 [ 3-methyl-l,2,4-triazol-l-yl
928 OCH CH2CH3 CF3 I 3-methyl-l,2,4-triazol-2-yl
929 OCH2CH2CH3 CF2CF3 I 3-methyl-l,2,4-triazol-2-yl
930 OCH2CH2CH3 CF3 I 2-ethyl-2H-tetrazol-5-yl
931 OCH CH2CH CF2CF3 I 2-ethyl-2H-tetrazol-5-yl 932 OCH2CH2CHg CF3 [ 1-ethyl- lH-tetrazol-5-yl 933 OCH CH2CHg CF2CF3 [ 1-ethyl- lH-tetrazol-5-yl 934 OCH CH2CH3 CF3 I 2-isopropyl-2H-tetrazol-5-yl 935 OCH2CH2CH CF2CF3 I 2-isopropyl-2H-tetrazol-5-yl
936 OCH2CH2CH3 CF3 I 1-isopropyl- lH-tetrazol-5-yl
937 OCH2CH CHg CF2CF3 I 1-isopropyl- lH-tetrazol-5-yl
938 OCH CH CHg CF3 I 2-prop ar gyl- 2H-tetr azol- 5 -yl
939 OCH2CH CHg CF2CF3 I 2-propargyl-2H-tetrazol-5-yl
940 OCH CH CH3 CFg I 1-propargyl- lH-tetrazol-5-yl
941 OCH2CH2CH3 CF2CF3 I 1-propargyl- lH-tetrazol-5-yl
942 OCH2CH2CH3 CF3 I 4,5-dimethyHmidazol-l-yl
943 OCH2CH CH3 CF2CF3 I 4, 5-dimethyHmidazol- 1-yl
944 OCH2CH2CH3 CF3 I 4,5-dibromoimidazol-l-yl
945 OCH2CH2CH3 CF2CF3 I 4, 5-dibromoimidazol- 1-yl
946 OCH2CH2CH3 CF3 I 4-trifluoromethyHmidazol- 1-yl
947 OCH CH2CH3 CF2CFg I 4-trifluoromethyHmidazol- 1-yl
948 OCH2CH2CHg CF3 I 4-cyanoimidazol- 1-yl
949 OCH CH2CHg CF2CF3 I 4-cyanoimidazol- 1-yl
950 OCH2CH2CH3 CF3 I 4,5-diiodoirαidazol-l-yl
951 OCH2CH2CH3 CF2CF3 I 4,5-diiodoimidazol-l-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-l,2,4-triazol-l-yl
955 OCH2CF2H CF2CF3 I 3-methyl-l,2,4-triazol-l-yl
956 OCH2CF2H CF3 I 3-methyl- 1, 2,4-triazol-2-yl
957 OCH2CF2H CF2CF3 I 3-methyl- l,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 OCH2CF H CF3 I 1-ethyl- lH-tetrazol-5-yl
961 OCH2CF2H CF2CFg I 1-ethyl- lH-tetrazol-5-yl
962 OCH2CF2H CF3 I 2-isopropyl-2H-tetrazol-5-yl
963 OCH2CF2H CF CF3 I 2-isopropyl-2H-tetrazol-5-yl
964 OCH2CF2H CF3 I 1-isopropyl- lH-tetrazol-5-yl
965 OCH2CF2H CF2CF3 I 1-isopropyl- lH-tetrazol-5-yl
966 OCH2CF2H CF3 I 2-prop ar gyl- 2H-tetrazol- 5 -yl
967 OCH2CF2H CF2CF3 I 2-propargyl-2H-tetrazol-5-yl
968 OCH2CF2H CF3 I 1-propargyl- lH-tetrazol-5-yl
969 OCH2CF2H CF2CF3 I 1-propargyl- lH-tetrazol-5-yl
970 OCH2CF2H CF3 I 4,5-dimethyHmidazol-l-yl
971 OCH2CF2H CF2CF3 I 4, 5-dimethylimidazol- 1-yl
972 OCH2CF2H CF3 I 4, 5-dibromoimidazol- 1-yl
973 OCH2CF2H CF2CFg I 4, 5-dibromoimidazol- 1-yl
974 OCH2CF2H CF3 I 4-trifluoromethyHmidazol- 1 -yl
975 OCH2CF2H CF2CF3 I 4-trifluoromethyHmidazol- 1-yl
976 OCH2CF2H CF3 I 4-cyanoimidazol-l-yl 977 OCH2CF2H CF2CF3 I 4-cyanoimidazol-l-yl 978 OCH2CF2H CF3 I 4, 5-diiodoimidazol- 1-yl 979 OCH2CF2H CF2CF3 I 4,5-diiodoimidazol-l-yl 980 OCH(CH3)2 CF3 I 4,5-dichloroimidazol-l-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-l,2,4-triazol-2-yl
985 OCH(CHg)2 CF2CF3 I 3-methyl-l,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- lH-tetrazol-5-yl
989 OCH(CH3)2 CF2CF3 I 1-ethyl- lH-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- lH-tetrazol-5-yl
993 OCH(CH3)2 CF2CF I 1-isopropyl- lH-tetrazol-5-yl
994 OCH(CH3)2 CF3 I 2-propargyl-2H-tetrazol-5-yl
995 OCH(CH3)2 CF CF3 I 2-propargyl-2H-tetrazol-5-yl
996 OCH(CH3)2 CF3 I 1-propargyl- lH-tetr azol- 5-yl
997 OCH(CH3)2 CF2CF3 I 1-pr op argyl- lH-tetr azol- 5 -yl
998 OCH(CH3)2 CF3 I 4,5-dimethyHmidazol-l-yl
999 OCH(CH3)2 CF CF3 I 4, 5-dimethyHmidazol- 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-trifluoromethyHmidazol- 1-yl
1003 OCH(CH3)2 CF2CF3 I 4-trifluoromethyHmidazol- 1-yl
1004 OCH(CH3)2 CF3 I 4-cyanoimidazol- 1-yl
1005 OCH(CH3)2 CF CF3 I 4-cyanoimidazol- 1-yl
1006 OCH(CH3)2 CF3 I 4, 5-diiodoimidazol- 1-yl
1007 OCH(CH3)2 CF2CF I 4, 5-dnodoimidazol- 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-l,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- lH-tetrazol-5-yl
1017 H CF2CF3 I 1-ethyl- lH-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- lH-tetrazol-5-yl
1021 H CF2CF3 I 1-isopropyl- lH-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- lH-tetrazol-5-yl
1025 H CF2CF3 I 1 -prop argyl- lH-tetrazol- 5 -yl
1026 H CFg I 4, 5-dimethyHmidazol- 1-yl 145-148
1027 H CF2CF3 I 4,5-dimethyHmidazol-l-yl
1028 H CF3 I 4,5-dibromoimidazol-l-yl 88-90 1029 H CF2CF3 I 4,5- dibromoimidazol- 1-yl
1030 H CF3 I 4-trifluoromethyHmidazol- 1-yl 109-110
1031 H CF2CF3 I 4-trifluoromethyHmidazol- 1-yl
1032 H CF3 I 4-cyanoimidazol-l-yl 117-119
1033 H CF2CF3 I 4-cyanoimidazol-l-yl
1034 H CF3 I 4,5-dnodoimidazol-l-yl
1035 H CF2CF3 I 4, 5-dnodoimidazol- 1-yl
1036 CH3 CFg I 4, 5-dichloroimidazol- 1-yl
1037 CH3 CF2CF3 I 4, 5 - dichloroimidazol- 1-yl
1038 CH3 CF3 I 3-methyl-l,2,4-triazol-l-yl 107-110
1039 CH3 CF2CF3 I 3-methyl-l,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-l,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- lH-tetrazol- 5 -yl
1045 CH3 CF2CF3 I 1-ethyl- lH-tetrazol-5-yl
1046 CH3 CFg I 2-isopropyl-2H-tetrazol-5-yl
1047 CH3 CF2CFg I 2-isopropyl-2H-tetrazol-5-yl
1048 CH3 CFg I 1-isopropyl- lH-tetrazol-5-yl
1049 CH3 CF2CFg I 1-isopropyl- lH-tetrazol-5-yl
1050 CH3 CFg I 2-propargyl-2H-tetrazol-5-yl
1051 CH3 CF2CFg I 2-propargyl-2H-tetrazol-5-yl
1052 CH3 CFg I 1-propargyl- lH-tetrazol-5-yl
1053 CH3 CF2CFg I 1-propargyl- lH-tetrazol-5-yl
1054 CH3 CFg I 4, 5-dimethyHmidazol- 1-yl 132-135
1055 CH3 CF CFg I 4, 5-dimethyUmidazol- 1-yl
1056 CH3 CFg I 4, 5-dibromoimidazol- 1-yl
1057 CH3 CF2CF3 I 4,5-dibromoimidazol-l-yl
1058 CH3 CFg I 4-trifluoromethyHmidazol- 1-yl 103-106
1059 CH3 CF2CFg I 4-trifluoromethyHmidazol- 1-yl
1060 CH3 CFg I 4-cyanoimidazol- 1-yl 145-147
1061 CH3 CF2CFg I 4-cyanoimidazol- 1-yl
1062 CHg CFg I 4, 5-dnodoimidazol- 1-yl 200-202
1063 CH3 CF2CF3 I 4, 5-dnodoimidazol- 1-yl
1064 CH2CH3 CFg I 4, 5-dichloroimidazol- 1-yl
1065 CH2CH3 CF2CFg I 4,5-dichloroimidazol-l-yl
1066 CH2CH3 CFg I 3-methyl-l,2,4-triazol-l-yl
1067 CH2CH3 CF2CF3 I 3-methyl- 1, 2,4-triazol- 1-yl
1068 CH CH3 CFg I 3-methyl-l,2,4-triazol-2-yl
1069 CH2CH3 CF2CFg I 3-methyl- l,2,4-triazol-2-yl
1070 CH2CH3 CFg 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- lH-tetr azol- 5-yl 99-100 1073 CH2CH3 CF2CF3 I 1-ethyl- lH-tetr azol- 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- lH-tetrazol-5-yl 98-99
1077 CH2CHg CF2CF3 I 1-isopropyl- lH-tetrazol-5-yl
1078 CH CH3 CF3 I 2-propargyl-2H-tetrazol-5-yl 64
1079 CH2CH3 CF2CF3 I 2-prop ar gyl- 2H-tetr azol- 5 -yl
1080 CH2CH3 CF3 I 1 -prop argyl- lH-tetr azol- 5 -yl oil
1081 CH2CH3 CF2CF3 I 1-propargyl- lH-tetrazol-5-yl
1082 CH2CH3 CF3 I 4, 5-dimethyHmidazol- 1-yl
1083 CH2CH3 CF2CF3 I 4,5-dimethyHmidazol-l-yl
1084 CH2CH3 CF3 I 4, 5-dibromoimidazol- 1-yl
1085 CH2CH3 CF2CF3 I 4,5-dibromoimidazol-l-yl
1086 CH2CH3 CF3 I 4-trifluoromethyHmidazol- 1-yl
1087 CH2CH3 CF2CF3 I 4-trifluoromethyHmidazol- 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-l-yl
1094 CF3 CF3 I 3-methyl-l,2, 4-triazol-l-yl
1095 CF3 CF2CF3 I 3-methyl- 1,2, 4-triazol- 1-yl
1096 CF3 CF3 I 3-methyl-l,2,4-triazol-2-yl
1097 CF3 CF2CFg I 3-methyl-l,2,4-triazol-2-yl
1098 CF3 CFg I 2-ethyl-2H-tetrazol-5-yl
1099 CF3 CF2CFg I 2-ethyl-2H-tetrazol-5-yl
1100 CF3 CFg I 1-ethyl- lH-tetrazol-5-yl
1101 CF3 CF2CFg I 1-ethyl- lH-tetrazol-5-yl
1102 CF3 CFg I 2-isopropyl-2H-tetrazol- 5 -yl
1103 CF3 CF2CF3 I 2-isopropyl-2H-tetrazol-5-yl
1104 CF3 CF3 I 1-isopropyl- lH-tetrazol-5-yl
1105 CFg CF2CF3 I 1-isopropyl- lH-tetrazol-5-yl
1106 CF3 CF3 I 2-prop ar gyl- 2H-tetr azol- 5 -yl
1107 . CF3 CF2CF3 I 2-prop ar gyl-2H-tetr azol- 5 -yl
1108 CF3 CF3 I 1-propargyl- lH-tetrazol-5-yl
1109 CF3 CF2CF3 I 1-propargyl- lH-tetrazol-5-yl
1110 CF3 CF3 I 4, 5-dimethyHmidazol- 1-yl
1111 CF3 CF2CF3 I 4, 5-dimethyHmidazol- 1-yl
1112 CF3 CF3 I 4,5-dibromoimidazol-l-yl 1113 CF3 CF2CF3 I 4,5-dibromoimidazol-l-yl 1114 CF3 CF3 I 4-trifluoromethylimidazol- 1-yl 1115 CF3 CF2CF3 I 4-trifluoromethyHmidazol- 1-yl 1116 CF3 CF3 I 4-cyanoimidazol-l-yl 1117 CF3 CF2CF3 I 4-cyanoimidazol-l-yl 1118 CF3 CF3 I 4, 5-dnodoimidazol- 1-yl 1119 CF3 CF2CF3 I 4,5-cUiodoimidazol- 1-yl

Claims

Claims
1. Pyrimidine derivatives represented by the formula (1),
Figure imgf000050_0001
(1 ) wherein R1 is H, Ci-Cgalkyl (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), C^Cealkoxy (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), Cx-Cealkylthio (being optionally substituted by one or more of halogen), Cx-Cβalkylsulfinyl (being optionally substituted by one or more of halogen), C-L-Cealkylsulfonyl (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(0)R5, R2 is polyfluoroC1-C6alkyl,
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, CrC6alkyl (being optionally substituted by one or more of halogen); 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-l-yl, l,2,3-triazol-2-yl, 1,2,4-triazol-l-yl, l,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).
2. A fungicide for agricultural and horticultural use, comprising one or more of the pyrimidine derivatives represented by a formula (1)
Figure imgf000051_0001
(1)
wherein R1 is H, Cι-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), CpCβalkoxy (being optionally substituted by one or more of halogen), C2-C6alkenyloxy (being optionally substituted by one or more of halogen), C2-
Cβalkynyloxy (being optionally substituted by one or more of halogen), Ci-Cβalkylthio (being optionally substituted by one or more of halogen), Ci-Cgalkylsulfϊnyl (being optionally substituted by one or more of halogen), Ci-Cβalkylsulfonyl (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(0)R5,
R2 is polyfluoroCi-C6alkyl,
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, Cι-C6alkyl (being optionally substituted by one or more of halogen); 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-l-yl, l,2,3-triazol-2-yl, 1,2,4-triazol-l-yl, l,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), as the active principle and carrier.
PCT/US2004/020114 2003-08-15 2004-06-23 Fungicidal pyrimidine derivatives Ceased WO2005019207A1 (en)

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WO2007083692A1 (en) * 2006-01-23 2007-07-26 Kumiai Chemical Industry Co., Ltd. Aminopyridine derivative and plant disease control agent for agricultural or horticultural use
WO2009019099A1 (en) * 2007-08-09 2009-02-12 Basf Se Tetrasubstituted pyrimidine derivatives for controlling phytopathogenic fungi
WO2009138712A3 (en) * 2008-05-13 2010-09-16 Syngenta Limited Chemical compounds
WO2019141972A1 (en) * 2018-01-16 2019-07-25 Globachem Nv Agricultural chemicals
WO2023136142A1 (en) * 2022-01-17 2023-07-20 日本曹達株式会社 Heteroarylpyrimidine compound and pest control agent

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WO2021095577A1 (en) * 2019-11-14 2021-05-20 ユニマテック株式会社 Fluorine-containing pyrazole compound and method for producing same

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007083692A1 (en) * 2006-01-23 2007-07-26 Kumiai Chemical Industry Co., Ltd. Aminopyridine derivative and plant disease control agent for agricultural or horticultural use
WO2009019099A1 (en) * 2007-08-09 2009-02-12 Basf Se Tetrasubstituted pyrimidine derivatives for controlling phytopathogenic fungi
WO2009138712A3 (en) * 2008-05-13 2010-09-16 Syngenta Limited Chemical compounds
WO2019141972A1 (en) * 2018-01-16 2019-07-25 Globachem Nv Agricultural chemicals
CN111601796A (en) * 2018-01-16 2020-08-28 环球化学股份有限公司 Agricultural chemicals
US11440900B2 (en) 2018-01-16 2022-09-13 Globachem Nv Agricultural chemicals
WO2023136142A1 (en) * 2022-01-17 2023-07-20 日本曹達株式会社 Heteroarylpyrimidine compound and pest control agent

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