EP0046337A2
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EP
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Triazole compounds, a process for preparing them, their use as plant and pharmaceutical fungicides and as plant growth regulators and compositions containing them
Assignee: Imperial Chemical Industries Ltd
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Filing: 1981-07-16
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Granted: —
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Expires: 2001-07-16
Abstract
Abstract Racemic compounds of formula: and stereoisomers thereof, wherein R' is alkyl, cyclo alkyl or optionally substituted phenyl; R 2 is a heterocyclic group; and Az is 1 ,2,4-triazolyl radical; and their acid addition salts, ethers, esters and metal complexes; have fungicidal activity useful in the agricultural and pharmaceutical fields. They are also capable of regulating plant growth.
Inventors
- 👤 Peter Hilary Freeman
- 👤 Paul Anthony Worthington
- 👤 William George Rathmell
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-28 06:50
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/12; A; A01; A01N; A01N43/00; A01N43/64; A01N43/647; A01N43/653; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
52 words
A racemic compound having the general formula (1) : and stereoisomers thereof, wherein R 1 is alkyl, cycloalkyl (e.g. cyclopropyl, cyclopentyl or cyclohexyl) or optionally substituted phenyl and R 2 is a heterocyclic group; and Az is a 1, 2, 4-triazolyl radical; and acid addition salts, metal complexes, ethers and esters thereof.
Claim 2
Dependent Claim
52 words
A racemic compound having the general formula (1) : and stereoisomers thereof, wherein R 1 is alkyl, cycloalkyl (e.g. cyclopropyl, cyclopentyl or cyclohexyl) or optionally substituted phenyl and R 2 is a heterocyclic group; and Az is a 1, 2, 4-triazolyl radical; and acid addition salts, metal complexes, ethers and esters thereof.
Claim 3
Dependent Claim
20 words
A compound according to claim 1 wherein Az is a 1, 2, 4-triazol-1-yl radical or a 1, 2, 4-triazol-4-yl radical.
Claim 4
Dependent Claim
37 words
A triazole compound according to claim 1 or claim 2 wherein R 1 is an alkyl group which is a straight or branched chain alkyl group having from 1 to 6, especially 1 to 4, carbon atoms.
Claim 5
Dependent Claim
32 words
A triazole compound according to claim 1 or claim 2 wherein R 1 is phenyl or phenyl substituted with halogen, C l-5 alkyl, C l-4 alkoxy, halo-alkoxy, trifluoromethyl, nitro, phenyl or phenoxy.
Claim 6
Dependent Claim
70 words
A triazole compound according to any of claims 1, 2 and 4 wherein R 1 is phenyl, 2-, 3-, or 4-chlorophenyl, 2, 4- or 2,6-dichlorophenyl, 2-, 3-, or 4-fluorophenyl, 2,4-or 2,6-difluorophenyl, 2-, 3-, or 4-bromophenyl, 2-chloro-4-fluorophenyl, 2-chloro-6-fluorophenyl, 2-, 3-, or 4-methoxyphenyl, 2-, 3-, or 4-nitrophenyl, 2-, 3-, or 4-methylphenyl, 2-, 3-, or 4-t-butylphenyl, 2-, 3-, or 4-trifluoromethylphenyl, 2-, 3-, or 4-phenoxyphenyl, and 2-, 3-, or 4-phenylphenyl (2-, 3-, or 4-biphenylyl).
Claim 7
Dependent Claim
27 words
A triazole compound according to any of claims 1 to wherein R 2 is an unsubstituted, or halo- or alkyl-substituted, thiophene, furan, pyridine, pyrimidine or pyrrole ring.
Claim 8
Dependent Claim
39 words
A compound having the formula : wherein R 1 is phenyl, 2- or 4-, chloro- or fluoro-, phenyl, or 2, 4-dichlorophenyl, or 2, 4-difluorophenyl, and R 2 is 2-thienyl, 2-[5-chlorothienyl, 2-furyl, 2-(5-- butylfuryl), 2-, 3- or 4-pyridyl or 2-thienyl.
Claim 9
Dependent Claim
39 words
A compound having the formula : wherein R 1 is phenyl, 2- or 4-, chloro- or fluoro-, phenyl, or 2, 4-dichlorophenyl, or 2, 4-difluorophenyl, and R 2 is 2-thienyl, 2-[5-chlorothienyl, 2-furyl, 2-(5-- butylfuryl), 2-, 3- or 4-pyridyl or 2-thienyl.
Claim 10
Dependent Claim
20 words
A compound according to claim 4 wherein R 1 is phenyl or halophenyl and R 2 is 2-[5-chlorothienyl] or 2-thienyl.
Claim 11
Dependent Claim
3 words
The compound :
Claim 12
Dependent Claim
3 words
The compound :
Claim 13
Dependent Claim
81 words
A process for preparing a compound as defined in any of claims 1 to 9 which comprises reacting a compound of general formula (II) or (III) : in which R 1 and R 2 are as defined in any of the preceeding claims and X is a halogen atom (preferably a chlorine or bromine atom), with 1, 2, 4-triazole, either in the presence of an acid-binding agent or in the form of one of its alkali metal salts, in a solvent.
Claim 14
Dependent Claim
83 words
Ill A process according to claim 10 wherein the compounds of general formula (II) and (III) are prepared by reacting a compound of general formula (IVa) or (IVb) : wherein R 1 , R and X are as defined above with, respectively, a Grignard compound of general formula (Va) or (Vb) : wherein R 1 and R 2 are as defined above and Y is a halogen (preferably chlorine, bromine or iodine) in a convenient solvent such as diethyl ether or tetrahydrc furan.
Claim 15
Dependent Claim
56 words
A process according to claim 10 wherein the compounds of general formula (II) wherein R 1 is unsubstituted or substituted phenyl and R 2 is a heterocyclic group are prepared by reacting the appropriate ketone of general formula (VI) wherein R 1 and R 2 are as defined with dimethyl oxosulphonium methylide or dimethyl sulphonium methylide.
Claim 16
Dependent Claim
27 words
A process according to claim 12 wherein the ketone of general formula (VI) is prepared, using the Friedel-Crafte reaction, or by methods set cut in the literatures
Claim 17
Dependent Claim
18 words
As novel intermediates epoxides and halohydrins as defined in claim 10 and ketones as defined in clair.. 12.
Claim 18
Dependent Claim
33 words
A plant fungicidal composition comprising, as an active ingredient, a compound according to any of claims 1 tc 9, or a salt, metal complex, ether cr ester thersef and carrier or diluent therefor.
Claim 19
Dependent Claim
62 words
A method of combating fungal diseases in a plant, or for regulating plant growth, which method compriser applying to the plant, to seed of the plant, or to the locus of the plant or seed, a compound, or a salt, metal complex, ether or ester therefor, as defined in any of clains to 9, or a composition as defined in claim 15.
Claim 20
Dependent Claim
36 words
A pharmaceutical or veterinary composition which comprises a compound according to any of claims 1 to 9, or a salt, metal complex, ether or ester thereof, together with a pharmaceutically or veterinary acceptable diluent or carrier.
Claim 21
Dependent Claim
42 words
18 A method of treatment of candidiasis or human dermatophyte infections which comprises administering to a human or animal an effective amount of a compound as claimed in any cf claims 1 to 9 or a composition as claimed in claim 16.
References Cited (Backward Citations)
No citation records indexed.
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