Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ester doai
Patent
1988-06-27
1990-02-20
Ford, John M.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ester doai
564200, 514628, 558414, C07C10334, C07C12200, A01N 3734, A01N 3718
Patent
active
049027158
DESCRIPTION:
BRIEF SUMMARY
The invention concerns certain 4-monohalo-2,2-dimethyl-3-oxobutyric acid anilides substituted on the phenyl radical and the use of these compounds as fungicidal-active materials.
The use of 4-chloro-3-oxobutyric acid anilide in seed material disinfection is described by C. H. Arndt (Plant Diseases Reporter 34, p. 334 (1950), correspondingly in Chemical Abstracts, 45, 2129 (1951)). From EP-PS 7 089 (published on the 16th September 1981, N. Haberle et al., Consortium fur Elekrochemische Industrie GmbH) is known the use of 2-methylpent-4-enoic acid 3',4'-dichloroanilide and 2-methylbut-3-enoic acid 3',5'-dichloroanilide against spores of Fusarium nivale and Tilletia tritici.
It was the task of the invention to make available fungicides with broader activity spectrum. Furthermore, it was the task of the present invention to make available fungicides which manifest satisfactory action even in the case of small applied amounts. Furthermore, it was the task of the invention to prepare fungicidal-active materials with high compatibility for cultivated plants.
In the scope of the present invention, these tasks are solved by compounds of the formula ##STR2## wherein X is a halogen atom, R the same or different substituents in any desired position of the benzene ring, namely, halogen atoms, C.sub.1 -C.sub.3 -alkyl groups, trifluoromethyl groups or cyano groups and n a whole number with a value of 1, 2 or 3.
As residues X, Cl, Br, I, especially Br, are preferred.
As residues R are preferred F, Cl, Br, I, methyl groups, trifluoromethyl groups and cyano groups.
Increasedly effective as fungicides are compounds of the formula (I) in which X stands for a chlorine, bromine or iodine atom and R.sub.n signifies a trifluoromethyl radical in 3-position or, in all, 3 methyl radicals each in the 2, 4 and 6 position.
The compounds of formula (I) according to the invention can be prepared, for example, in that one reacts compounds of the formula ##STR3## wherein Y signifies a chlorine or bromine atom, with compounds of the formula ##STR4## In the formulae (II) and (III), X, R and n can, in each case, have the same meanings as in formula (I).
The reaction is preferably carried out in the presence of substances binding hydrogen halides, especially in the presence of tertiary amines. Examples of such tertiary amines are tributylamine, N,N-dimethylaniline, pyridine and the like.
The reaction is preferably carried out in a solvent. Examples of suitable solvents are acetic acid ethyl ester, acetone, diethyl ether, dioxan and the like.
In order to suppress side reactions, such as the formation of the corresponding 3,3-dimethylpyrrolidine-2,4-diones, it is recommended to carry out the reaction at relatively low temperature and in the presence of a solvent.
Temperatures of 5.degree. C. to 35.degree. C., especially of 10.degree. C. to 25.degree. C., are preferred. The solvents are preferably used substantially free of water.
Those compounds of the formula (I), in which X signifies an iodine atom, are expediently prepared by Finkelstein reaction from the corresponding compounds of the formula (I), in which X signifies a chlorine or bromine atom, i.e. by reaction with alkali metal iodide in acetone or a solvent of similar properties.
The compounds of formula (II) used as starting materials are obtainable, for example, by the reaction of dimethylketene with alpha-haloacetic acid halides according to DE-OS 33 08 175.
The starting materials of formula (III) are commercially available or can be prepared according to known processes.
In the following Tab. 1 are set out examples of the compounds of formula (I) according to the invention.
TAB. NO. 1 __________________________________________________________________________
active melting
material sum point in
No. chemical designation
formula .degree.C.
__________________________________________________________________________
1 4-chloro-2,2-dimethyl-3-oxo-
C.sub.12 H.sub.13 ClFNO.sub.2
111
butyric acid 2'-fluoroanilide
2 4-chloro-2,2-dimethyl-3-oxo-
C.sub.12 H.sub.13 ClFNO.sub.
REFERENCES:
patent: 4552983 (1985-11-01), Tenud et al.
W. T. Brady et al, "The Reaction of Dimethylketen With Some Acid Halides", J.O.C.S.(C), 1970, pp. 2522-2523.
Haberle Norman
Reutter Anneliese
Schilling Bernd
Brookens Ronald G.
Ford John M.
Jones S. Preston
The Dow Chemical Company
Whittenbaugh Robert C.
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