FLUTOLANIL

FLUTOLANIL Basic information
Product Name:FLUTOLANIL
Synonyms:3'-Isopropoxy-2-trifluoromethylbenzanilide;Flutalanil;N-[3-(Isopropyloxy)phenyl]-2-(trifluoromethyl)benzamide;NNF 136;MONCUT;MONCUT(R);FLUTOLANIL, 250MG, NEAT;flutolanil (bsi,draft e-iso,draft f-iso)
CAS:66332-96-5
MF:C17H16F3NO2
MW:323.31
EINECS:
Product Categories:F;Fungicides;Amide structurePesticides&Metabolites;E-GMethod Specific;Endocrine Disruptors (Draft)Alphabetic;Pesticides;FA - FL;Alpha sort;EPA
Mol File:66332-96-5.mol
FLUTOLANIL Structure
FLUTOLANIL Chemical Properties
Melting point 108° (Araki, Yabutani); mp 104-105° (Araki, 1985)
Boiling point 339.1±42.0 °C(Predicted)
density 1.2463 (estimate)
vapor pressure 6.5 x 10-6 Pa (25 °C)
storage temp. 0-6°C
solubility Chloroform (Slightly), Methanol (Slightly)
Water Solubility 6.53 mg l-1 (20 °C)
pka12.44±0.70(Predicted)
form Solid
color White to Pale Orange
LogP3.700
EPA Substance Registry SystemFlutolanil (66332-96-5)
Safety Information
RTECS CV5581320
Hazardous Substances Data66332-96-5(Hazardous Substances Data)
ToxicityLD50 in male and female rats, male and female mice (mg/kg): >10,000, >10,000 orally; in male and female rats (mg/kg): >5000 dermally (Araki)
MSDS Information
FLUTOLANIL Usage And Synthesis
UsesAgricultural fungicide.
UsesFlutolanil is used to control Basidiomycetes diseases in rice, cereals, sugar beet and other crops.
UsesFlutolanil is a fungicide that has been used for controlling brown patch on creeping bentgrass fairways.
DefinitionChEBI: Flutolanil is a member of the class of benzamides, obtained by formal condensation of the carboxy group of 2-(trifluoromethyl)benzoic acid with the amino group of 3-(ispropyloxy)aniline. A fungicide used to control a range of pathogens especially Rhizoctonia spp. on rice, turf and other crops. It has a role as an EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor and an antifungal agrochemical. It is a member of benzamides, an aromatic ether, a member of (trifluoromethyl)benzenes and a benzanilide fungicide.
Safety ProfileLow toxicity by ingestion, skincontact, intraperitoneal, and subcutaneous routes. Whenheated to decomposition it emits toxic vapors of NOx andF??.
Metabolic pathwayFlutolanil is an analogue of mepronil in which the methyl group is replaced by trifluoromethyl. Both compounds have systemic activity. This change in structure should render flutolanil more biostable by hindering hydrolysis and removing the option of methyl hydroxylation and further oxidation. This seems to be borne out in practice in that most of the metabolism of flutolanil occurs via O-dealkylation and aryl hydroxylation. Hydrolysis has not been detected.
DegradationFlutolanil is a stable arylamide with no particularly weak link in its comparatively simple chemistry. It is stable over the pH range 3-11 and it is stable to heat (PM). It is stable in sunlight (PM) but it was slowly degraded in 50% aqueous ethanol solution irradiated with a high pressure mercury lamp whilst bubbling oxygen through the solution (Tsao and Eto, 1991). The study was conducted using non-radiolabelled compound. No degradation occurred in the absence of oxygen. Even under these conditions, the addition of photosensitisers was required to give a reasonable amount of breakdown. With 5% acetone in the solution, 20% degradation was obtained in 8 hours. Almost no decomposition occurred on a glass surface in 8 hours unless a sensitiser (e.g. benzophenone) was added. This gave 40% decomposition.
The products in solution and on surfaces were different, as shown in Scheme 1. The major product (80%) in solution was 2-(trifluoromethyl)- benzamide (2). The benzoic acid (3) was identified as a minor product. The N-ethoxycarbonyl derivative (4) was due to reaction with the solvent. Amide bond cleavage was postulated to occur via oxidation in the aniline ring (Tsao and Eto, 1991; Yumita et al., 1984). The resulting phenolic products and anilines were converted into unidentified polar polymers.
No product 2 was obtained by irradiation on a glass surface (Tsao and Eto, 1991). Under these conditions 3'-hydroxy-2-(trifluoromethyl)benzanilide (5), i.e. dealkylated flutolanil, and a rearrangement product (6) were the main products. Flutolanil is therefore an extremely stable compound which undergoes slow photo-oxidation rather than aqueous photolysis.

Trichloroisocyanuric acid FLUOROIMIDE DITHIANON Fluxapyroxad 3-ISOPROPOXYANILINE METHYL-(2-TRIFLUOROMETHYL-BENZYL)-AMINE 2-(TRIFLUOROMETHYL)BENZYLAMINE FLUTOLANIL SOLUTION 100UG/ML IN METHANOL 1ML 2-(TRIFLUOROMETHYL)BENZAMIDE Mepronil 2-(Trifluoromethyl)benzaldehyde FLUTOLANIL

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