EP0243014A1
Expired / Lapsed
EP
⏱️ 0.0 years remaining
Fungicides
Assignee: Imperial Chemical Industries Ltd
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Filing: 1987-03-31
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Granted: —
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Expires: 2007-03-31
Abstract
Abstract Compounds of formula (1): and stereoisomers thereof, wherein W is R 1 O 2 -C=CH-ZR 2 , wherein R' and R 2 , which are the same or different, are alkyl or fluoroalkyl groups, and Z is either an oxygen or sulphur atom; A is an oxygen or sulphur atom,-NR 3 -, or-CR 4 R 5 -; X, Y and Z 1 , which are the same or different, are hydrogen or halogen atoms, or hydroxy, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted heteroarylalkyl, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted arylalkoxy, optionally substituted aryloxy, optionally substituted heteraryloxy. optionally substituted acyioxy, optionally substituted amino, optionally substituted acylamino, optionally substituted arylazo, nitro, cyano,-CO 2 R 6 ,-CONR 7 R 8 ,-COR 9 -CR=NR 10 , -CR=NOR 10 or -N=CR 11 R 12 groups; or the groups X and Y, when they are in adjacent positions on the ring, optionally join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; and R, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R" and R", which are the same or different, are hydrogen atoms (provided that R 4 and R 5 are not hydrogen) or optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted heterarylalkyl, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl or optionally substituted heteroaryl groups; and metal complexes thereof. The compounds are useful in agriculture, especially as fungicides but also as insecticides and plant growth regulators.
Inventors
- 👤 Vivienne Margaret Anthony
- 👤 John Martin Clough
- 👤 Paul De Fraine
- 👤 Kevin Beautement
- 👤 Christopher Richard Ayles Godfrey
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-07 12:46
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/30; C07D207/32; C07D207/33; C07D207/337; A; A01; A01N; A01N43/00; A01N43/02; A01N43/04; A01N43/06; A01N43/34; A01N43/36; A01N43/38; A01N43/48; A01N43/58; C07D209/00; C07D209/02; C07D209/04; C07D209/10; C07D209/18; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/54; C07D307/77; C07D307/78; C07D307/79; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/24; C07D333/50; C07D333/52; C07D333/54; C07D333/60
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
282 words
A compound of formula (I) : and stereoisomers thereof, wherein W is R 1 O 2 C-C=CH-ZR 2 , wherein R i and R 2 , which are the same or different, are alkyl or fluoroalkyl groups, and Z is either an oxygen or sulphur atom; A is an oxygen or sulphur atom, -NR 3 -, or -CR 4 R 5- ; X, Y and Z 1 , which are the same or different, are hydrogen or halogen atoms, or hydroxy, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted heteroarylalkyl, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted arylalkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted acyloxy, optionally substituted amino, optionally substituted acylamino, optionally substituted arylazo, nitro, cyano, -CO 2 R 6 , -CONR 7 R 8, - COR 9 , -CR=NR 10 , -CR=NOR 10 , or -N=CR 11 R 12 groups or the groups X and Y, when they are in adjacent positions on the ring, optionally join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; and R, R 3, R4, R 5 , R6, R7, R 8 , R 9 , R 10 , R 11 and R 12 , which are the same or different, are hydrogen atoms (provided that R 4 and R 5 are not both hydrogen) or optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted heteroarylalkyl, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl or optionally substituted heteroaryl groups; and metal complexes thereof.
Claim 2
Dependent Claim
282 words
A compound of formula (I) : and stereoisomers thereof, wherein W is R 1 O 2 C-C=CH-ZR 2 , wherein R i and R 2 , which are the same or different, are alkyl or fluoroalkyl groups, and Z is either an oxygen or sulphur atom; A is an oxygen or sulphur atom, -NR 3 -, or -CR 4 R 5- ; X, Y and Z 1 , which are the same or different, are hydrogen or halogen atoms, or hydroxy, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted heteroarylalkyl, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted arylalkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted acyloxy, optionally substituted amino, optionally substituted acylamino, optionally substituted arylazo, nitro, cyano, -CO 2 R 6 , -CONR 7 R 8, - COR 9 , -CR=NR 10 , -CR=NOR 10 , or -N=CR 11 R 12 groups or the groups X and Y, when they are in adjacent positions on the ring, optionally join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; and R, R 3, R4, R 5 , R6, R7, R 8 , R 9 , R 10 , R 11 and R 12 , which are the same or different, are hydrogen atoms (provided that R 4 and R 5 are not both hydrogen) or optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted heteroarylalkyl, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl or optionally substituted heteroaryl groups; and metal complexes thereof.
Claim 3
Dependent Claim
88 words
A compound according to claim 1 wherein X, Y and Z 1 are selected from the group consisting of hydrogen, halogen, C 1-4 alkyl, aryl(C 1-4 )alkyl, heteroaryl(C 1-4 )alkyl, heteroaryloxy(C 1-4 )alkyl, heteroaryloxy, aryloxy(C 1-4 )alkyl, C 1-4 alkoxy, aryl(C 1-4 )alkoxy, aryloxy, aryl(C 2-4 )alkenyl, heteroaryl(C 2-4 )alkenyl, aryl(C 2-4 )alkynyl, heteroaryl(C 2 _ 4 )alkynyl, cyano, C 1-4 alkoxycarbonyl and aryloxycarbonyl, one of X, Y and Z 1 being other than hydrogen and in a position on the heterocyclic ring adjacent to the group W.
Claim 4
Dependent Claim
18 words
A compound according to claim 1 or 2 in which R 1 and R 2 are both methyl.
Claim 5
Dependent Claim
38 words
A compound of formula (IA): wherein.X, which is in a position adjacent to the acrylate group, is halogen, C 1-4 alkyl, halo(C 1-4 )-alkyl, aryl(C 1-4 )alkyl, aryloxy(C 1-4 )alkyl, aryl(C 2 _ 4 )alkenyl, aryloxy or acyl.
Claim 6
Dependent Claim
38 words
A compound of formula (IA): wherein.X, which is in a position adjacent to the acrylate group, is halogen, C 1-4 alkyl, halo(C 1-4 )-alkyl, aryl(C 1-4 )alkyl, aryloxy(C 1-4 )alkyl, aryl(C 2 _ 4 )alkenyl, aryloxy or acyl.
Claim 7
Dependent Claim
53 words
A compound of formula (IB): wherein R 3 is hydrogen, C 1-4 alkyl or aryl(C 1-4 )-alkyl; X is hydrogen, C 1-4 alkyl, aryl(C 1-4 )alkyl, aryl(C 2-4 )alkenyl or acyl; and Y and Z 1 are hydrogen; or when X is hydrogen, Y and Z 1 together form a fused benzene ring.
Claim 8
Dependent Claim
53 words
A compound of formula (IB): wherein R 3 is hydrogen, C 1-4 alkyl or aryl(C 1-4 )-alkyl; X is hydrogen, C 1-4 alkyl, aryl(C 1-4 )alkyl, aryl(C 2-4 )alkenyl or acyl; and Y and Z 1 are hydrogen; or when X is hydrogen, Y and Z 1 together form a fused benzene ring.
Claim 9
Dependent Claim
269 words
A process for preparing a compound of formula (I) according to claim 1 which comprises: (i) treating a ketoester of formula (II): with a phosphorane of formula Ph 3 P + . - CH(ZR 2 ) in a convenient solvent; or (ii) eliminating the elements of the alcohol R 2 ZH from an acetal of formula (X): under either acidic or basic conditions; or when Z is oxygen, (iii) treating a compound of formula (XIII): wherein R 13 is a metal atom with a species R 2 Q , or wherein R 13 is hydrogen successively with a base and a species R 2 Q; or (iv) successively treating an acrylic acid derivative of formula (XII): with bromine, a reagent of formula R 2 0M and sodium hydrogen sulphate, or when Z is sulphur, (v) treating a ketoester of formula (II) with a lithio-species of formula (CH 3 ) 3 SiCH(Li)SR 2 ; or (vi) treating an enol of formula (XIII) wherein R 13 is hydrogen, with a thiol of formula R 2 SH under acidic conditions optionally in the presence of a dehydrating agent; or (vii) treating a beta-chloroacrylate of formula (XV): with a thiolate of formula R 2 SM; or (viii) treating a beta-sulphonyloxyacrylate of formula (XVI): with a thiolate of formula R 2 SM; wherein A, X , Y , Z, Z 1 , R 1 and R 2 have the meanings given in claim 1, Ph is phenyl, R 13 is hydrogen or a metal atom, Q is a leaving group, and M is a metal atom or a metal atom with an associated halogen.
Claim 10
Dependent Claim
13 words
The intermediate chemicals of formulae (II) and (IX) to (XVII) as defined herein.
Claim 11
Dependent Claim
13 words
The intermediate chemicals of formulae (II) and (IX) to (XVII) as defined herein.
Claim 12
Dependent Claim
27 words
A fungicidal composition comprising, as an active ingredient, a fungicidally effective amount of a compound according to claim 1 and a fungicidally acceptable carrier or diluent therefor.
Claim 13
Dependent Claim
29 words
A method of combating fungi which comprises applying to plants or seeds, or to their locus, a compound according to claim 1 or a composition according to claim 8.
Claim 14
Dependent Claim
29 words
An insecticidal or plant growth regulating composition comprising, as an active ingredient, an effective amount of a compound according to claim 1 and an acceptable carrier or diluent therefor.
Claim 15
Independent Claim
27 words
A method of killing insect pests which method comprises administering to the insect or to its locus, an effective amount of an insecticidal compound of formula (I).
Claim 16
Independent Claim
27 words
A method of killing insect pests which method comprises administering to the insect or to its locus, an effective amount of an insecticidal compound of formula (I).
Claim 17
Dependent Claim
28 words
A method of regulating plant growth which comprises applying to a plant an effective amount of a plant growth regulating compound of formula (I) according to claim 1.
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