| Identification | More | [Name]
Mepronil | [CAS]
55814-41-0 | [Synonyms]
2-methyl-n-(3-(1-methylethoxy)phenyl)benzamide
2-METHYL-N-(3-PROPAN-2-YLOXYPHENYL)-BENZAMIDE
3'-Isopropoxy-2-methylbenzanilide
BASITAC
BASITAC(R)
MEPRONIL
2-methyl-n-(3-(1-methylethoxy)phenyl)-benzamid
b1-2459
Benzamide, 2-methyl-N-(3-(1-methylethoxy)phenyl)-
kco-1
N-(3-Isopropoxyphenyl)-2-methylbenzamide
MEPRONIL PESTANAL
2-Methyl-3'-isopropoxybenzanilide
mepronil (bsi,draft-iso,jmaf)
MEPRONILSTANDARD
3'-iso-propoxy-2-toluanilide
BI 2459
3'-Isopropyloxy-2-methylbenzanilide | [Molecular Formula]
C17H19NO2 | [MDL Number]
MFCD00144739 | [Molecular Weight]
269.34 | [MOL File]
55814-41-0.mol |
| Hazard Information | Back Directory | [Uses]
Mepronil is an benzanilide based fungicide found in the raw materials of herbal medicine. | [Uses]
Mepronil is used to control Basidiomycetes diseases in rice,
cereals, potatoes, vegetables, sugar beet, fruit, vines, tobacco, turf grass
and other crops. | [Definition]
ChEBI: A member of the class of benzamides, obtained by formal condensation of the carboxy group of 2-methylbenzoic acid with the amino group of 3-(ispropyloxy)aniline. A fungicide used to control diseases caused by Basidomycetes including Rhizoctonia | [Metabolic pathway]
Mepronil is an analogue of flutolanil containing a 2-methyl group as
opposed to the 2-trifluoromethyl group. The compounds have the same
mode of action and are metabolised via similar routes except that the
methyl group of mepronil provides an extra site for metabolic attack.
The compound is metabolised by dealkylation and hydroxylation at
both the methyl and isopropyl groups and by aryl hydroxylation. Some
hydrolysis occurs in plants and animals. | [Degradation]
Mepronil is stable to light, heat and air and in solution over a pH range of
3-10. It is hydrolysed under strongly alkaline conditions (PM). Mepronil
on a silica gel surface exposed to sunlight between September and
December (Japan) was 66% degraded with an estimated half-life of 36
days. This could be shortened by the addition of the photosensitiser xanthone
(Yumita and Yamamoto, 1982). Irradiation of an aqueous solution
with UV light at 30 °C afforded 32% degradation in 80 hours. 14C-Aniline
and 14C-carbonyl labelling was used in these experiments. Carbonyl label
afforded marpally more metabolites, indicating that some amide bond
cleavage occurred. Twelve photo-products were identified and four
unknowns were detected. Aqueous photolysis afforded somewhat fewer
products than the surface irradiation. Hydroxylation occurred initially at
four positions in the molecule and these were followed by further oxidation,
hydrolysis, cyclisation or cleavage. The products are shown in
Scheme 1. The major products (5-10%) of surface photolysis were compounds
2, 3 and 4 and on aqueous photolysis were 6 and 13 with an
unknown derived only from carbonyl labelling. |
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