Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1988-06-15
1990-02-13
Springer, David B.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C07D207404
Patent
active
049008404
DESCRIPTION:
BRIEF SUMMARY
The invention concerns certain N-substituted 3-halosuccinimides, a process for their preparation, as well as the use of these compounds as fungicidal-active materials.
In DE-AS 20 12 656 and in JP Kokai 75 129 743 are described some N-substituted 3-halosuccinimides as fungicidal-active materials.
It was the task of the invention to prepare new substances with high fungicidal effectiveness. A further task of the present invention was to make available fungicidal-active substances with wide activity spectrum. In particular, it was the task of the present invention to prepare substances which still show satisfectory effectiveness against fungus strains in which a substantial resistance towards N-(3,5-dichlorophenyl)-substituted dicarboximides is present. Furthermore, it was, in particular, the task of the present invention to make available fungicidal substances which show good effectivenesses not only against Botrytis cinerea but also against the types of fungus frequently accompanying this fungus, such as for example Alternaria types or Penicillium types.
In the scope of the present invention, these tasks were solved in that compounds of the formula ##STR2## were synthesised, wherein R signifies a chlorine, bromine or iodine atom, n 0, 1, 2 or 3, X, X' and Z each the same or different residues, namely, hydrogen atoms, fluorine atoms or methyl groups and Y a hydrogen, fluroine, chlorine or bromine atom or a methyl group, with the proviso that for n=0 and at the same time R=Cl, at least one of the residues X, X', Y and Z is not a hydrogen atom and that when Z does not signify a hydrogen atom, at least one of the residues X, X' and Y also does not signify a hydrogen atom.
Preferred are compounds of the formulae ##STR3## wherein R, n, X, Y have the same meanings as for formula (I), whereby the residues X are, in each case, the same residues and L and N signify the same or different residues, namely, methyl groups or fluroine atoms, and M signifies a hydrogen atom or a methyl group.
Especially preferred because of their fungicidal effectiveness are those compounds of the formulae (II) and (III) for which R signifies a bromine atom, especially those of the formula ##STR4## wherein n, X and Y have the meanings given for formula (I), whereby the residues X are, in each case, the same residues.
In formula (IV), the residues X preferably each signify two hydrogen atoms or two methyl groups.
Because of its especially high fungicidal effectiveness, the compound of the formula ##STR5## is especially preferred.
The 3-halosuccinimides of formula (I) according to the invention are optically active because of a centre of asymmetry on the carbon atom in 3-position on the heterocycle. It is entirely possible that one of the enantiomers in question (3-R- or 3-S-enantiomer) contributes more strongly than the other to the desired action. By the expression "compounds of the formula" are, in every case, to be understood the optically pure 3-R- or 3-S-enantiomers, as well as all mixtures of at least one 3-R- with at least one 3-S-isomer, for example the corresponding racemates.
The compounds according to the invention are, for example, preparable as follows:
1. By reaction of compounds of the formula ##STR6## with those of the formula t,0051 ##STR7## to give the corresponding hemi-amides and ring closure in the presence of agents promoting the condensation, for example acetyl chloride;
2. By reaction of compounds of the formula ##STR8## (preparable according to 1. from maleic acid anhydride and compounds of the formula (VII) with hydrogen halides of the formula HR in a suitable solvent, for example trichloromethane.
3. It is especially advantageous when, for the preparation of compounds of the formula (I) according to the invention, compounds of the formula ##STR9## are reacted with those of the formula signifies a chlorine or bromine atom, and, if R signifies an iodine atom, the so obtained product of the formula ##STR10## is subsequently reacted in per se known manner with alkali metal iodide, preferably sodium iodide, preferably
REFERENCES:
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patent: 4276090 (1981-06-01), Becker et al.
Pyriadi, J. Org. Chem., 37, pp. 4184-4186 (1972).
Cotter et al., J. Org. Chem., 26, 10-15 (1960).
Feuer et al., J. Amer. Chem. Soc., 80, 5873-5877 (1958).
Feuer, J. Org. Chem., 36, 3372-3376 (1971).
Pyriadi et al., J. Org. Chem., 36, 821-823 (1971).
Haberle Norman
Reutter Anneliese
Brookens Ronald G.
Jones S. Preston
Springer David B.
The Dow Chemical Company
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