Anilide derivatives as fungicides

Details Anilide derivatives as fungicides Anilide derivatives as fungicides

1996-09-18

1998-05-26

Rotman, Alan L.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514188, 546 6, 546292, 546288, 546289, C07F 314, C07D21364, A01N 4340

Patent

active

057565244

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/GB 95/00570 filed 03/16/95.


FIELD OF THE INVENTION

This invention relates to new derivatives of anthranilic acid useful as fungicides.


PRIOR ART

DE 2417216 discloses inter alia, N-phenylcarbamoylpyridine compounds as fungicides in which the pyridine is substituted by chlorine and the phenyl can be substituted by carboxy. In J. Agric. Biol. Chem 44(9), 2143, 1980, certain N-benzoylanthranilates are described as fungicides. Similar compounds are disclosed in GB 1,563,664 and Japanese Kokai 53130655. We have found that certain novel anthranilic acid derivatives also have valuable fungicidal activity and also have advantages over compounds disclosed in these publications.


DISCLOSURE OF THE INVENTION

According to the invention there is provided a compound of formula I ##STR2##
X is O or S;
A is a 6 membered heteroaryl group comprising at least one nitrogen atom, which is optionally substituted by one or more of the group R.sup.2 ;
R.sup.1 is alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl, Y.sup.1 --X-- or amino, (each of which is optionally substituted), halogen, cyano, nitro, acyl, acyloxy, optionally substituted heterocyclyl or optionally substituted phenyl; or two adjacent groups together with the carbon atoms to which they are attached can form an optionally substituted benzo ring;
R.sup.2 has the same meaning as R.sup.1 or two adjacent groups together with the carbon atoms to which they are attached can form an optionally substituted heterocyclic ring;
Y is alkyl, cycloalkyl, cycloalkenyl, alkenyl or alkynyl, each of which is optionally substituted, hydrogen or acyl;
Y.sup.1 has the same meaning as Y or is optionally substituted phenyl or optionally substituted heterocyclyl
Z is C(.dbd.X.sup.1)--X.sup.2 --R.sup.3, cyano, optionally substituted heterocyclyl, --C(R.sup.5).dbd.N--OR.sup.6 or --C(R.sup.5).dbd.N--NR.sup.6 R.sup.7 ;
R.sup.3 is alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl, phenyl or heterocyclyl, each of which is optionally substituted, hydrogen or an inorganic or organic cationic group.
X.sup.1 and X.sup.2, which may be the same or different, are O or S;
R.sup.5, R.sup.6 and R.sup.7, which may be the same or different, are alkyl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl, phenyl or heterocyclyl, each of which is optionally substituted or hydrogen or R.sup.6 and R.sup.7 together with the atom(s) to which they are attached can form a ring;
n is 0 to 4,
together with complexes with metal salts, as well as salts with bases of compounds which are acids and salts with acids of compounds which are bases, with the proviso that when Y is hydrogen and
i) when Z is carboxy, methoxycarbonyl or ethoxycarbonyl ring A is not unsubstituted pyridyl or pyrazinyl; and
ii) when Z is carboxy and n is 0, A is not 2-chloro-3-pyridyl, 6-(2-diethylaminoethoxy)-3-pyridyl or a 2-pyridyl group.
Alkyl groups are preferably of 1 to 20, eg 1 to 6, carbon atoms. Alkenyl and alkynyl groups are generally of 3 to 6 carbon atoms. Cycloalkyl or cycloalkenyl groups are preferably of 3 to 8 carbon atoms.
Substituents, when present on any alkyl, cycloalkyl, cycloalkenyl, alkenyl or alkynyl moiety include halogen, azido, cyano, optionally substituted alkoxy, optionally substituted alkylthio, hydroxy, nitro, optionally substituted amino, acyl, acyloxy, optionally substituted phenyl, optionally substituted heterocyclyl, optionally substituted phenoxy and optionally substituted heterocyclyloxy.
Cycloalkyl or cycloalkenyl groups may also be substituted by alkyl.
Substituents when present on any phenyl group are usually one or more of the same groups as defined for R.sup.1.
The term heterocyclyl includes both aromatic and non- aromatic heterocyclyl groups. Heterocyclyl groups are generally 5, 6 or 7-membered rings containing up to 4 hetero atoms selected from nitrogen, oxygen and sulfur. Examples of heterocyclyl groups are furyl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, imidazolyl, dioxolanyl, oxazolyl, thiazolyl, imidazolyl, imidazolinyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazol

REFERENCES:
Chemical Abstracts, vol. 77(17)abst.No. 114,078(b),Oct. 23, 1972.
Chemical Abstracts, vol. 84(7)abst.No. 39,707v Feb. 16, 1976.
Chemical Abstracts, vol. (3),abst.No. 15765u, Jan. 16, 1978.
O. Kirino et al., "Fungicidal Activity of N-benzoylanthranilates and Related Compounds", Agricultural and Biological Chemistry, vol. 44, No. 9, 1980, Tokyo, Japan, pp. 2143-2147.

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