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1. (EP0527182) PREPARATION OF PROPENOIC ACID DERIVATIVES.

Office : European Patent Office
Application Number: 91908886 Application Date: 01.05.1991
Publication Number: 0527182 Publication Date: 17.02.1993
Publication Kind : A1
Designated States: DE, FR, GB
Prior PCT appl.: Application Number:GB1991000695 ; Publication Number: Click to see the data
IPC:
C 07C
A01N 37/36
C 07D
A01N 43/78
C07C 323/56
C07D 277/36
C07D 277/74
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
323
Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
50
containing thio groups and carboxyl groups bound to the same carbon skeleton
51
having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
56
the carbon skeleton containing six-membered aromatic rings
A HUMAN NECESSITIES
01
AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
N
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
37
Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
36
containing at least one carboxylic group or a thio-analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio-analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
277
Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
02
not condensed with other rings
20
having two or three double bonds between ring members or between ring members and non-ring members
32
with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
36
Sulfur atoms
A HUMAN NECESSITIES
01
AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
N
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
43
Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
72
having rings with nitrogen atoms and oxygen or sulfur atoms, as ring hetero atoms
74
five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
78
1,3-Thiazoles; Hydrogenated 1,3-thiazoles
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
323
Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
50
containing thio groups and carboxyl groups bound to the same carbon skeleton
51
having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
56
the carbon skeleton containing six-membered aromatic rings
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
277
Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
02
not condensed with other rings
20
having two or three double bonds between ring members or between ring members and non-ring members
32
with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
36
Sulfur atoms
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
277
Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
60
condensed with carbocyclic rings or ring systems
62
Benzothiazoles
68
with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
70
Sulfur atoms
74
Sulfur atoms substituted by carbon atoms
CPC:
C07D 277/36
A01N 37/36
A01N 43/78
C07C 323/56
C07D 277/74
Y02P 20/55
Applicants: SCHERING AGROCHEMICALS LTD
Inventors: FOSTER R W G SCHERING AGROCHEM
Priority Data: 9009916 02.05.1990 GB
Title: (DE) HERSTELLUNG VON PROPENSÄUREDERIVATEN.
(EN) PREPARATION OF PROPENOIC ACID DERIVATIVES.
(FR) PREPARATION DE DERIVES D'ACIDE PROPENOIQUE.
Abstract:
(EN) Compounds of formula (I) and salts thereof, wherein m is 0 to 18, R1 is alkyl, and R is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, optionally substituted heterocyclyl(thio)carbonyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted N-substituted iminomethylene or substituted heterocyclylidenemethyl are obtained by (A) attaching a protecting group, W, on the hydroxy group of a compound of formula (II) to give a compound of formula (III); (B) replacing a hydrogen on the methyl of the compound of formula (III) with a leaving group, Z, to give a compound of formula (IV); (C) treating the compound of formula (IV) with a compound of formula (V): R-(CH2)m-SH to give a compound of formula (VI) and (D) removing the protecting group. The compounds of formula (I) are novel and have fungicidal activity and are intermediates for the preparation of other useful fungicidal compounds. Many of the compounds of formula (VI) are also fungicidal.
(FR) Cette invention décrit des composés représentés par la formule (I) et des sels de ces composés, où m représente 0 à 18, R1 représente un alkyle et R représente un aryle, un hétéroaryle, un hétérocyclyle, un hétérocyclyl(thio)carbonyle, un alcényle, un alkynyle, un iminoéthylène N-substitué, ou un hétérocyclylidèneméthyle, tous facultativement substitués. Ces composés sont obtenus (A) en attachant un groupe protecteur, W, au groupe hydroxyle d'un composé ayant la formule (II) pour produire un composé ayant la formule (III), (B) en remplaçant un hydrogène sur le méthyle du composé de la formule (III) par un groupe à substituer, Z, pour produire un composé de formule (IV), (C) en traitant le composé de formule (IV) avec un composé de formule (V): R-(CH2)m-SH pour produire un composé de formule (VI) et (D) en enlevant le groupe protecteur. Les composés de formule (I) sont nouveaux et font preuve d'une activité fongicide. Ils sont aussi des intermédiaires pour la préparation d'autres composés fongicides utiles. Plusieurs des composés de formule (VI) sont aussi fongicides.
Also published as:
WO/1991/017152