66332-96-5

Flutolanil is a systemic fungicide. It has a low aqueous solubility, volatile with a marginal risk of leaching to groundwater. It is persistent in both soils and aquatic systems. Although it has a low mammalian toxicity it does show some potential to bioaccumulate. No serious risks to human health have been identified. It is moderately toxic to birds and most aquatic organisms and earthworms but has a low toxicity to honeybees.

The pure product is white, odorless crystals. Its mp is 108°C (102-103°C) and its vapor pressure is 1.77×10-9 Pa (20°C). Its solubility at 20°C is: acetone 642 g/L, methanol 606 g/L (480 g/L), chloroform 341 g/L (238 g/L), toluene 56 g/L (65 g/L), xylene 29 g/L, hexane 3 g/L, and water 9.6 mg/L. Its partition coefficient is 3.7. It is stable in aqueous solutions with a pH of 3-9. It shows no decomposition when heated at 100°C for 5 hours or stored at 50°C for 14 days. Its decomposition rate is 1% under fluorescent light (17,000 lx, 96 hours), indicating good stability to heat and light. Its half-life in soil is 40-60 days.

Flutolanil(66332-96-5) is used to control Basidiomycetes diseases in rice, cereals, sugar beet and other crops.

Agricultural fungicide.

Flutolanil 40SC Fungicide(66332-96-5) is a systemic fungicide for control of Basidiomycete diseases on turf. This product has shown excellent safety on Kentucky bluegrass, annual bluegrass, annual and perennial ryegrass, red fescue, tall fescue, bentgrass, Bermudagrass, zoysiagrass, and St. Augustine grass. Flutolanil 40SC Fungicide may be tank mixed with other labeled fungicides.

ChEBI: 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.

Flutolanil is commercially produced through a multi-step synthesis involving substituted anilines and heterocyclic intermediates, optimised for systemic fungicidal activity. It begins with the preparation of 2-trifluoromethylbenzanilide derivatives, which are key to its fungicidal properties. These intermediates are constructed by reacting 2-trifluoromethylbenzoic acid with aniline under acylation conditions, typically using reagents like thionyl chloride or phosphorus oxychloride to form the amide bond. The resulting compound is then further functionalised with a phenyl-substituted isoxazole ring, introduced via cyclisation reactions involving hydroxylamine and beta-diketones. The process is carried out under controlled temperature and solvent conditions to ensure high yield and purity.

MONCUT

Low toxicity by ingestion, skincontact, intraperitoneal, and subcutaneous routes. Whenheated to decomposition it emits toxic vapors of NOx andF??.

Flutolanil 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.

Flutolanil(66332-96-5) 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.

Flutolanil(66332-96-5) is a SDHI (Succinate-dehydrogenase inhibitor) with narrow spectrum. Flutolanil has inhibitory effect against development of each step of the infection cycle. Inhibition of invasion from sclerotium and mycelial growth result in preventive and curative effect in infection, respectively。

Fungicide