Pyrazolecarboxamide derivative and fungicide containing it as ac

Details Pyrazolecarboxamide derivative and fungicide containing it as ac Pyrazolecarboxamide derivative and fungicide containing it as ac

1986-03-31

1988-05-03

Jiles, Henry R.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

548376, 548377, 548378, A01N 4356, C07D23114, C07D23116

Patent

active

047420740

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to a pyrazolecarboxamide derivative (referred to as "present compound" hereinafter) represented by the formula ##STR2## wherein R.sup.1 and R.sup.2 which are identical or different and represent a hydrogen atom, a halogen atom, a methyl group, an ethyl group or a trifluoromethyl group, R.sup.3 represents a hydrogen atom or a methyl group and n represents 0 or 1, and a method for preparing the same and a fungicide containing the derivative as an active ingredient.
The inventors have made extensive research on pyrazolecarboxamide compounds and as a result, have found that the present compound represented by the formula [I] has preventive, curative and systemic controlling effects on plant microbes. The present invention is based on this finding.
The following are plant diseases on which the present compound has an excellent controlling effect; Rhizoctonia solani and Rhizoctonia oryzae, R. solani III B on rice plant; Puccinia striiformis, P. graminis, P. recondita, P. hordei, Rhizoctonia cerealis, Typhula incarnata, T. ishikariensis, Ustilago tritici and U. nuda on wheat; Rhizoctonia solani and Corticium rolfsii on various crops; Rhizoctonia solani on potato and beet; Gymnosporangium haraeanum on pear; Venturia inaequaris on apple; Rhizoctonia solani, Corticium rolfsii, Uromyces trifolii and Typhula incarnata, T. ishikariensis on pasture and lawn.
The present compound can be produced, for example, by the following methods. ##STR3## wherein R.sup.1, R.sup.2, R.sup.3 and n are as defined above, X represents a halogen atom and Ar represents a group having the formula: ##STR4## (wherein R.sup.3 and n are as defined above).
That is, a carboxylic acid halide represented by the formula [II], e.g., carboxylic acid chloride, carboxylic acid bromide and carboxylic acid fluoride, is reacted with a 4-aminoindane derivative represented by the formula [III] to obtain the present compound represented by the formula [I].
Reaction solvents are not essential for the above method, but generally inert solvents are used. As examples of the solvents, the following may be listed; hydrocarbons such as benzene, toluene, xylene, etc., halogenated hydrocarbons such as chloroform, dichloromethane, chlorobenzene, etc., ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, etc., ketones such as acetone, methyl isobutyl ketone, etc., esters such as ethyl acetate, etc., nitriles such as acetonitrile, etc., dimethylsulfoxide, sulfolane, dimethylformamide, dimethylacetamide, etc. and mixtures thereof.
The reaction may be carried out in the presence of an acid accepting agent. Examples of the acid accepting agent are organic bases such as triethylamine, pyridine, N,N-dimethylaniline, 4-dimethylaminopyridine, etc. and inorganic bases such as sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, etc.
Reaction temperature has no special limitation, but usually is 0.degree. C.-150.degree. C.
Amount of the starting compounds used in this reaction is generally 0.8-1.5 mol of the 4-aminoindane derivative represented by the formula [III] per 1 mol of the carboxylic acid halide represented by the formula [II]. ##STR5## wherein Ar is as defined above and R.sup.1' and R.sup.2' which are identical or different represent a methyl group or an ethyl group.
That is, firstly a diketone represented by the formula [IV] is reacted with an isocyanate represented by the formula [V] to obtain a carbamoyl diketone represented by the formula [VI], which is then reacted with methylhydrazine to obtain the present compound.
Reaction solvent is not essential for the reaction of the diketone represented by the formula [IV] with the isocyanate represented by the formula [V], but ordinarily inert solvents are used.
As examples of the solvents, the following are listed; hydrocarbons such as benzene, toluene, etc., halogenated hydrocarbons such as chloroform, dichloromethane, chlorobenzene, etc., ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane,

REFERENCES:
patent: 4134987 (1979-01-01), Huppatz
patent: 4460603 (1984-07-01), Chan

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