Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1994-05-06
1996-09-24
Ford, John M.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
544296, 544284, 544254, 544262, 544300, 544301, 544310, 544312, 544316, 544317, 544319, 544327, 544333, 544334, 544335, 504239, 504240, 504241, 504243, C07D23932, C07D40312, C07D40314, A01N 4354
Patent
active
055590810
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP92/02558, filed Nov. 2, 1992.
This invention concerns herbicidal sulfonamides, processes for their preparation, and compositions containing them.
EP 363040 and WO 91/10653 each disclose herbicidal sulfonanilides related to those of the present invention.
In one aspect, the invention provides novel sulfonamides of the formula: ##STR2## and salts thereof, where:
A represents a substituted or unsubstituted benzene ring, or a 5-membered substituted or unsubstituted heteroaromatic ring;
Q is --O--, --S-- or a group --CXX'--;
X and X', which may be the same or different, are each hydrogen, halogen, cyano, an optionally-substituted alkyl group, or a group --OR.sup.a, --SR.sup.a, or --COR.sup.b ; or one of X and X' represents hydroxy and the other is as defined above; or X and X' together represent .dbd.O or .dbd.S;
R.sup.a is an optionally-substituted alkyl, aryl or acyl group;
R.sup.b is an optionally-substituted alkyl or aryl group, or a group --OR.sup.c or --NR.sup.c R.sup.d ;
R.sup.c and R.sup.d, which may be the same or different, are each hydrogen, or an optionally-substituted alkyl or aryl group;
Y is nitrogen or a group CR.sup.9 ;
R.sup.1 is an optionally-substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl, benzoheterocyclyl or amino group;
R.sup.2 is hydrogen, an optionally-substituted alkyl or carboxylic acyl group, or a group --SO.sub.2 R.sup.1 ;
R.sup.3 and R.sup.4, which may be the same or different, are each hydrogen, halo, an optionally-substituted alkyl, alkoxy, cycloalkyl or amino group, or an optionally-substituted heterocyclyl group; and
R.sup.9 represents hydrogen or an optionally-substituted alkyl group;
with the proviso that, when Q is --O-- or --S--, the ring A is a 5-membered substituted or unsubstituted heteroaromatic ring;
and with the proviso that, when R.sup.1 is substituted alkyl, it is not a group of the formula: ##STR3## where X" is oxygen or sulfur, and R.sup.6, R.sup.7 and R.sup.8 are each hydrogen or optionally-substituted alkyl.
When A is a 5-membered heteroaromatic ring, it is preferably a substituted or unsubstituted thiophene, furan, pyrrole, thiazole, isothiazole, pyrazole, imidazole, oxazole or isoxazole ring.
In the ring A, any substituent on a carbon atom thereof is preferably halo, cyano, a group --COOR.sup.10 (where R.sup.10 represents hydrogen or an optionally-substituted alkyl group), or an optionally-substituted alkyl, alkoxy, aryloxy, heterocyclyloxy or amino group. Preferred such substituent groups are fluoro and chloro.
Any substituent on a nitrogen atom of the ring A is preferably a substituted or unsubstituted alkyl, alkoxy, amino or aryl group, especially a methyl group.
Any alkyl group present in the molecule is preferably of 1 to 8 carbon atoms, especially of 1 to 6 carbon atoms, and particularly of 1 to 4 carbon atoms. Specific preferred unsubstituted alkyl or alkyl-containing groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, methoxy, ethoxy and n-propoxy.
When any alkyl group in the molecule is substituted, this may for example be by one or more halogen atoms (eg fluorine, chlorine or bromine), alkoxy or alkylthio groups of 1 to 4 carbon atoms (eg methoxy or ethoxy), hydroxy, nitro, mercapto, amino, substituted amino, carbamoyl, substituted carbamoyl, thiocarbamoyl, substituted thiocarbamoyl, cyano, acyl, aryl or heteroaryl groups. Specific preferred substituted alkyl-containing groups include chloromethyl, bromomethyl, dichloromethyl, trifluoromethyl, difluoromethoxy, cyanomethyl, methoxyethyl and ethoxyethyl.
Any alkenyl or alkynyl group in the molecule is preferably of 2 to 6 carbon atoms, for example vinyl, allyl or propargyl. Any such alkenyl or alkynyl group is preferably unsubstituted, though it may if desired be substituted for example by halogen.
Any cycloalkyl group in the molecule is preferably of 3 to 7, especially of 5 or 6 carbon atoms, especially a cyclopentyl or cyclohexyl group. It is preferably unsubstituted.
Any aryl group in the molecule is preferably a phenyl group, w
REFERENCES:
Furya et al, Chemical Abstracts, vol. 105, entry 42476 (1986).
Gates Peter S.
Jones Graham P.
Saunders David E.
Agrevo UK Limited
Ford John M.
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