Microbicidal agents based on quinolonecarboxylic acid

Claim 1

A method of combating a plant fungus on plants or parts thereof which comprises applying to the fungus an effective amount for combating said fungus of a 1-cyclopropyl-1,4-dihydro-4-oxo-quinolinecarboxylic acid of the formula ##STR121## in which R 1 is hydrogen, fluorine, chlorine, bromine or nitro, R 2 is hydrogen, chlorine, fluorine or the group ##STR122## R 3 and R 4 each independently is alkyl or hydroxyalkyl which has 1 to 4 carbon atoms, or R 3 and R 4 , together with the nitrogen atom on which they are positioned, form a 5-membered or 6-membered saturated or partially unsaturated heterocyclic ring which can optionally contain in its ring oxygen, sulphur or an SO, SO 2 or NR 5 group and which is optionally substituted by at least one member selected from the group consisting of alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, phenyl and hydroxyl, R 5 is hydrogen, alkyl which has 1 to 12 carbon atoms and is optionally substituted by hydroxyl and alkoxy with 1 to 4 carbon atoms, or is phenylalkyl which has 1 to 3 carbon atoms in the alkyl part and is optionally substituted by nitro, amino or the group --O--CH 2 --O--, or is phenyl which is optionally substituted by at least one member selected from the group consisting of halogen, halogenoalkyl with 1 or 2 carbon atoms and with up to 5 halogen atoms, hydroxy, alkoxy with 1 to 3 carbon atoms, the group --O--CH 2 --O--, pyridyl, pyrimidinyl and the grouping ##STR123## A is an optionally substituted alkylene chain with 1 to 4 carbon atoms, R 6 is hydrogen, alkyl with 1 to 6 carbon atoms, or phenyl which is optionally substituted by at least one member selected from the group consisting of hydroxyl, methoxy and halogen, X is oxygen or the groupings ═NOR', ═N--NH--R" or (OR"') 2 , R' is hydrogen, alkyl with 1 to 6 carbon atoms, cycloalkyl with 5 or 6 carbon atoms, benzyl, chlorobenzyl or tetrahydropyranyl, R" is methyl, phenyl, carbamoyl or thiocarbamoyl, and R"' is methyl or ethyl, or (OR"') 2 represents ##STR124## or an acid addition, alkali metal, alkaline earth metal or heavy metal salt thereof which is tolerated by plants, or a hydrate thereof.

Claim 2

A method of combating a plant fungus on plants or parts thereof which comprises applying to the fungus an effective amount for combating said fungus of a 1-cyclopropyl-1,4-dihydro-4-oxo-quinolinecarboxylic acid of the formula ##STR121## in which R 1 is hydrogen, fluorine, chlorine, bromine or nitro, R 2 is hydrogen, chlorine, fluorine or the group ##STR122## R 3 and R 4 each independently is alkyl or hydroxyalkyl which has 1 to 4 carbon atoms, or R 3 and R 4 , together with the nitrogen atom on which they are positioned, form a 5-membered or 6-membered saturated or partially unsaturated heterocyclic ring which can optionally contain in its ring oxygen, sulphur or an SO, SO 2 or NR 5 group and which is optionally substituted by at least one member selected from the group consisting of alkyl with 1 to 6 carbon atoms, alkenyl with 2 to 6 carbon atoms, phenyl and hydroxyl, R 5 is hydrogen, alkyl which has 1 to 12 carbon atoms and is optionally substituted by hydroxyl and alkoxy with 1 to 4 carbon atoms, or is phenylalkyl which has 1 to 3 carbon atoms in the alkyl part and is optionally substituted by nitro, amino or the group --O--CH 2 --O--, or is phenyl which is optionally substituted by at least one member selected from the group consisting of halogen, halogenoalkyl with 1 or 2 carbon atoms and with up to 5 halogen atoms, hydroxy, alkoxy with 1 to 3 carbon atoms, the group --O--CH 2 --O--, pyridyl, pyrimidinyl and the grouping ##STR123## A is an optionally substituted alkylene chain with 1 to 4 carbon atoms, R 6 is hydrogen, alkyl with 1 to 6 carbon atoms, or phenyl which is optionally substituted by at least one member selected from the group consisting of hydroxyl, methoxy and halogen, X is oxygen or the groupings ═NOR', ═N--NH--R" or (OR"') 2 , R' is hydrogen, alkyl with 1 to 6 carbon atoms, cycloalkyl with 5 or 6 carbon atoms, benzyl, chlorobenzyl or tetrahydropyranyl, R" is methyl, phenyl, carbamoyl or thiocarbamoyl, and R"' is methyl or ethyl, or (OR"') 2 represents ##STR124## or an acid addition, alkali metal, alkaline earth metal or heavy metal salt thereof which is tolerated by plants, or a hydrate thereof.