66332-96-5

Basic information

• Product Name: FLUTOLANIL
• Synonyms: NNF 136;3'-Isopropoxy-2-trifluoromethylbenzanilide;Flutalanil;N-[3-(Isopropyloxy)phenyl]-2-(trifluoromethyl)benzamide;α,α,α-trifluoro-3'-isopropoxy-o-toluanilide;Flutolanil 250mg [66332-96-5];Flutolanil 0.1;alpha,alpha,alpha-trifluoro-3’-isopropoxy-o-toluanilide
• CAS NO: 66332-96-5
• Molecular Formula: C₁₇H₁₆F₃NO₂
• Molecular Weight: 323.31
• Product Categories: F;Fungicides;Pesticides;Amide structurePesticides&Metabolites;E-GMethod Specific;Endocrine Disruptors (Draft)Alphabetic;FA - FL;Alpha sort;EPA
• Mol File: 66332-96-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 108° (Araki, Yabutani); mp 104-105° (Araki, 1985)
• Boiling Point: 339.1 °C at 760 mmHg
• Flash Point: 158.9 °C
• Appearance: /
• Density: 1.2463 (estimate)
• Vapor Pressure: 9.38E-05mmHg at 25°C
• Refractive Index: 1.543
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 12.44±0.70(Predicted)
• Water Solubility: 6.53 mg l-1 (20 °C)
• CAS DataBase Reference: FLUTOLANIL(CAS DataBase Reference)
• NIST Chemistry Reference: FLUTOLANIL(66332-96-5)
• EPA Substance Registry System: FLUTOLANIL(66332-96-5)

Safety Data

• RTECS: CV5581320
• Hazardous Substances Data: 66332-96-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 66332-96-5 differently. You can refer to the following data:
1. Agricultural fungicide.
2. Flutolanil is used to control Basidiomycetes diseases in rice, cereals, sugar beet and other crops.
3. Flutolanil is a fungicide that has been used for controlling brown patch on creeping bentgrass fairways.

Safety Profile

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

Metabolic pathway

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.

Degradation

Flutolanil 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.

InChI:InChI=1/C17H16F3NO2/c1-11(2)23-13-7-5-6-12(10-13)21-16(22)14-8-3-4-9-15(14)17(18,19)20/h3-11H,1-2H3,(H,21,22)

Upstream product

• 41406-00-2 3-isopropoxyaniline 
• 312-94-7 2-trifluoromethylbenzoyl chloride 

Downstream Products

• 360-64-5 2-(trifluoromethyl)benzamide 
• 134314-54-8 N-ethoxycarbonyl-2-(trifluoromethyl)benzamide 
• 433-97-6 2-trifluoromethylbenzoic acid 
• 69392-32-1 3'-hydroxy-2-(trifluoromethyl)benzanilide 
• 134314-55-9 2'-amino-4'-isopropoxyphenyl 2-trifluoromethyl ketone 

Relevant articles and documents

PRESERVATIVE FOR PRESERVING WOOD AND METHOD FOR TREATING WOOD

The present invention relates to a preservative for preserving wood comprising 5-methyl-2-trifluoromethylfuran-3-carboxylic acid anilide derivative represented by the following formula, wherein R represents an iropropyl group or an isopropoxy group as an active ingredient. The preservative for preserving wood has an excellent preservative effect on various wood-decay fungi at an extremely low dose, is economically efficient, and imposes a small burden on the environment. The present invention also relates to a method for treating wood using the preservative.

Fungicidal composition for seed dressing

The present invention relates to a fungicidal composition intended for the protection of the multiplication products of cultivated plants, containing: (a) 2-(4-chlorobenzylidene)-5,5-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)-1-cyclopentanol; (b) one or more fungicides suitable for the protection of the said multiplication products, optionally one or more insecticides, (c), an agriculturally acceptable inert vehicle and an agriculturally acceptable surfactant. The invention also relates to a method for protecting the multiplication products of plants against fungal diseases using these compositions.