Kresoxim-methyl

Описание

Kresoxim-methyl is a strobilurin fungicide. It inhibits conidial germination of V. inaequalis isolates from apple orchards (EC₅₀s = 0.00033-0.0078 mg/L). Kresoxim-methyl also inhibits mycelial growth (EC₅₀ = 0.240 mg/L) and is fungicidal against Saprolegnia (MIC = 1 mg/L). It increases intracellular calcium levels and disrupts the mitochondrial membrane potential in mouse cortical cultures in a concentration-dependent manner. Kresoxim-methyl is toxic to goldfish (C. auratus; LC₅₀ = 0.807 mg/L).

Использование

Kresoxim-methyl is used for the control of several diseases (scab, mildews, blast, sheath blight and others) on a range of crops including apples, pears, vines, sugar beet and cereals.

Определение

ChEBI: A carboxylic ester that is the methyl ester of (2E)-(methoxyimino){2-[(2-methylphenoxy)methyl]phenyl}acetic acid. A fungicide for the control of scab on apples and pears and other fungal diseases on a wide range of crops.

Опасность

Moderately toxic by skin contact. Low tox-icity by ingestion and inhalation.

Профиль безопасности

Moderately toxic by skin contact. Low toxicity by ingestion and inhalation. Questionable carcinogen with experimental data reported. When heated to decomposition it emits toxic vapors of NOx.

Метаболический путь

By hepatocyte suspensions prepared from goats, pigs, hens, and rats that have been cryopreserved and thawed, BAS 490 F is metabolized via the same pathways as observed using fresh rat hepatocytes. The rate of hydrolysis of 14C-BAS 490 F leading to a carboxylic acid derivative seems to be constant between the cryopreserved and fresh hepatocytes except for goats. The oxidation reaction at the methyl group of the phenoxy ring, leading to the hydroxymethyl analog of the carboxylic acid of BAS 490 F, significantly decreases after cryopreservation, whereas the formation of (E)-2-methoxyimino-2[2-(4- hydroxy-2-methylphenyloxymethyl)phenyl] acetic acid by hydroxylation at the 4-position of the phenoxy ring remains at a constant rate. In pig hepatocytes, the two hydroxylated metabolites of the phenoxy ring, carboxy BAS 409 F and (E)-2-methoxyimino-2-o- hydroxymethylphenyl acetic acid, are formed to a lesser extent after cryopreservation.

Метаболизм

Kresoxim-methyl is rapidly metabolized in mammalian systems to the virtually inactive carboxylic acid, accounting for its low toxicity and high level of selectivity. Atharvest residues in cereals and top fruit are <0.05 mg/kg and <1 mg/kg in grapes and vegetables. The soil DT₅₀ = <3 days, and the Koc is 219 to 372. For the main metabolite, the Koc is 17 to 24. Hydrolytic stability tests indicate a DT₅₀ of 34 days at pH 7 but only 7 h at pH 9.