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FLUTOLANIL

CAS No.
66332-96-5
Chemical Name:
FLUTOLANIL
Synonyms
MONCUT;NNF 136;MONCUT(R);Flutalanil;FLUTOLANIL;Flutolanil 0.1;FLUTOLANIL STANDARD;Flufenacet Impurity 3;FLUTOLANIL, 250MG, NEAT;Flutolanil Solution, 1000ppm
CBNumber:
CB9478268
Molecular Formula:
C17H16F3NO2
Molecular Weight:
323.31
MDL Number:
MFCD00176914
MOL File:
66332-96-5.mol
Last updated:2023-05-25 18:01:23

FLUTOLANIL 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)
form Solid
Water Solubility 6.53 mg l-1 (20 °C)
pka 12.44±0.70(Predicted)
color White to Pale Orange
LogP 3.700
FDA UNII 2USL6Y9JZ4
Pesticides Freedom of Information Act (FOIA) Flutolanil
EPA Substance Registry System Flutolanil (66332-96-5)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS09
Signal word  Warning
Hazard statements  H410
Precautionary statements  P273-P391-P501
RTECS  CV5581320
Toxicity LD50 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)

FLUTOLANIL price More Price(3)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TRC F599430 Flutolanil 66332-96-5 500mg $180 2021-12-16 Buy
American Custom Chemicals Corporation AGR0000176 FLUTOLANIL 98.00% 66332-96-5 50ML $2728 2021-12-16 Buy
AHH MT-51868 Flutolanil 98% 66332-96-5 50ml $410 2021-12-16 Buy
Product number Packaging Price Buy
F599430 500mg $180 Buy
AGR0000176 50ML $2728 Buy
MT-51868 50ml $410 Buy

FLUTOLANIL Chemical Properties,Uses,Production

Uses

Flutolanil is a fungicide that has been used for controlling brown patch on creeping bentgrass fairways.

Uses

Flutolanil is used to control Basidiomycetes diseases in rice, cereals, sugar beet and other crops.

Uses

Agricultural fungicide.

Definition

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.

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.

41406-00-2
312-94-7
66332-96-5
Synthesis of FLUTOLANIL from 3-ISOPROPOXYANILINE and 2-(Trifluoromethyl)benzoyl chloride

FLUTOLANIL Suppliers

Global( 84)Suppliers
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Finetech Industry Limited 027-87465837 19945049750 sales@finetechnology-ind.com China 9591 58
J & K SCIENTIFIC LTD. 010-82848833 400-666-7788 jkinfo@jkchemical.com China 96815 76
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) FLUTOLANIL STANDARD α,α,α-trifluoro-3'-isopropoxy-o-toluanilide Flutolanil 250mg [66332-96-5] Flutolanil 0.1 A,A,A-TRIFLUORO-3'-ISOPROPOXY-O-TOLUANILIDE FLUTOLANIL alpha,alpha,alpha-trifluoro-3’-isopropoxy-o-toluanilide n-(3-(1-methylethoxy)phenyl)-2-(trifluoromethyl)-benzamid n-(3-(1-methylethoxy)phenyl)-2-(trifluoromethyl)benzamide N-(3-Isopropoxyphenyl)-2-(trifluoromethyl)benzamide Flutolanil Solution, 1000ppm Flutolanil@1000 μg/mL in Acetone Flutolanil @100 μg/mL in MeOH FlutolanilSolution,1,000mg/L,1ml Flutolanil Reference Material Flutolanil Solution in Toluene, 1000μg/mL Flufenacet Impurity 3 66332-96-5 C17H16F3NO2 F Fungicides Pesticides Amide structurePesticides&Metabolites E-GMethod Specific Endocrine Disruptors (Draft)Alphabetic FA - FL Alpha sort EPA