Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1996-02-02
1998-11-24
McKane, Joseph
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
504253, 5462681, 5462761, A01N 4340, C07D40112
Patent
active
058406549
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP94/00969 filed Mar. 25, 1994.
The present invention is concerned with certain 2,6-substituted pyridines, their preparation and use as herbicides.
Pyridines and pyridine derivatives have many uses, for example, as pharmaceuticals, pesticides (herbicides, acaricides, anthelmintics, bird repellants), feed supplements, solvents, reagents, intermediates, and chemicals for the polymer and textile industry. Various 2,6-diaryloxy- or -diarylmethoxy-pyridine derivatives have been investigated for such uses, the compounds often having additional substitution of the central pyridine ring.
The dibenzyloxy analogue of 2,6-diphenoxy-pyridine, in addition to being mentioned in JP-A-63250324, EP-A-180188 and J. Med. Chem, 10(2), pages 320 to 325, all medical research publications, was prepared as an example of the herbicidal compounds proposed in U.S. Pat. No. 3,535,328 and the divisional published as U.S. Pat. No. 3,687,959. Both texts are predominantly directed to the herbicidal, fungicidal, and, for the compounds claimed in U.S. Pat. No. 3,535,328, nematocidal and insecticidal activity, of amido or aminothioethoxy derivatives. No herbicidal activity data is given for the disclosed 2,6-dibenzyloxypyridine.
Applicants copending European Patent Applciation 92304795, filed 27th May 1992, (ref. T.1632 EPC) describes how certain substituted forms of 2,6-diphenoxypyridine and 2,6-dibenzyloxypyridine, and also the related asymmetric 2-phenoxy-6-benzyloxy pyridines, have a spectrum of herbicidal activity significantly different from the unsubstituted analogues in possessing post-emergence action against both grass-type plants and also broadleaf plants. Certain of those compounds are known per se, and said application claims their herbicidal application.
It has now been found, and forms the subject of the present invention, that good herbicidal activity is also present in related, novel pyridine derivatives having nitrogen-containing heteroaromatic substituents. In one embodiment, the present invention therefore provides 2,6-substituted pyridines of the formula I: ##STR1## wherein X represents an oxygen or sulphur atom; A represents an optionally substituted 5 or 6 membered nitrogen-containing heteroaromatic group; B represents an optionally substituted 5 or 6 membered cyclic hydrocarbon, alkyl, alkenyl, alkynyl, aryl or aralkyl group, or one of the meanings for A; R represents a halogen atom or an alkyl, haloalkyl, alkoxy, alkylthio or dialkylamino group; and m represents 0, 1 or 2.
Group A is suitably pyridyl, especially 4-pyridyl or pyrazolyl, especially 5-pyrazolyl, and group B is suitably one of such groups, or phenyl or benzyl. The groups A and B may be the same or different, and are preferably substituted, in particular having a substituent at the meta position (except for B-benzyl). The substituent groups may be any of those customarily employed in the modification and/or development of pesticidal compounds and are especially substituents that maintain or enhance the herbicidal activity associated with the compounds of the present invention, or influence persistence of action, soil or plant penetration, or any other desirable property of such herbicidal compounds. There may be one or more of the same or different substituents present in each radical.
Optional substituents in groups A and/or B include halogen atoms and nitro, cyano, alkyl, haloalkyl, alkoxy, alkylthio and aryl groups. Preferred substituents are a halogen, especially chlorine, atom, or an alkyl or haloalkyl group of 1 to 6 carbon atoms.
An alkyl group, either as a substituent on one or other of groups A and B, or as group R, may have a straight or branched chain, suitably containing up to 12, preferably 1 to 6, carbon atoms. In a haloalkyl group, whether as a substituent on one or other of groups A and B, or as group R, the halogen atom may be one or more fluorine, chlorine, bromine or iodine atoms, with fluorine being preferred and trifluoromethyl the preferred haloalkyl group.
Preferred compounds are those wherein each
REFERENCES:
patent: 3535328 (1970-10-01), Zielinski
patent: 3687959 (1972-08-01), Zielinski
patent: 4046553 (1977-09-01), Takahashi et al.
patent: 4213774 (1980-07-01), Schurter et al.
patent: 4267336 (1981-05-01), Nishiyama et al.
patent: 4309547 (1982-01-01), Koch et al.
patent: 4317913 (1982-03-01), Cartwright
patent: 4324627 (1982-04-01), Cartwright
patent: 4325729 (1982-04-01), Rempfler et al.
patent: 4493730 (1985-01-01), Kimura et al.
patent: 5155113 (1992-10-01), Fujii
patent: 5374604 (1994-12-01), Kleeman et al.
CA Registry No.: 142802-49-1; 142802-50-4; 142802-51-5; 142802-52-6; 141212-69-3; 139140-52-6; 129452-57-9; 129452-27-3; 12620907-2; 126209-12-9; 96591-92-3; and 94377-81-2, CAS Registry Handbook, 1992.
J. Med. Chem 10, 320-325, Mertes et al., Approaches to . . . deazauridine, 1996.
CA 113: 132173v Pyrazole . . . Active Ingredients.
Haga et al., p. 652, 1990.
CA 116: 106314; Preparation . . . Fungicides. Ohsumi et al., p. 781, 1992.
American Cyanamid Company
Mazzarese Joseph M.
McKane Joseph
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