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Details

Stereochemistry ACHIRAL
Molecular Formula C17H16F3NO2
Molecular Weight 323.3096
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUTOLANIL

SMILES

CC(C)OC1=CC(NC(=O)C2=C(C=CC=C2)C(F)(F)F)=CC=C1

InChI

InChIKey=PTCGDEVVHUXTMP-UHFFFAOYSA-N
InChI=1S/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)

HIDE SMILES / InChI
Flutolanil is a systemic fungicide for use specifically against basidiomycetes. It inhibits the hyphal growth and infection cushion formation. It is effective against silver scurf, daylily rust, snow mold, yellow patch (R cerealis), southern blight (Sclerotium rolfsii), red thread (Laetisaria fuciformis), fairy ring, all strains of brown patch (Rhizoctonia solani) and even Asian soybean rust (Phakopsora pachyrhizi). Flutolanil is used in crops such as artichokes, beetroot, Brussel sprouts, etc. It has season-long efficacy when applied to seed potatoes. It can be applied to foliage, to soil, or paddy water and as a seed treatment. Flutolanil is extremely safe for both crops and operator. Biochemical mode of action of flutolanil seems to be inhibition of a succinate dehydrogenase complex, an important enzyme complex in the respiratory chain of basidiomycetous fungi but not of fungi in other classes.

CNS Activity

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
The effects of fungicides on the phylloplane yeast populations of creeping bentgrass.
2002 Jun
Pesticide exposure in dwellings near bulb growing fields in The Netherlands: an explorative study.
2004
Investigation of the estrogenic activities of pesticides from Pal-dang reservoir by in vitro assay.
2007 Dec 15
Assessment of human pregnane X receptor involvement in pesticide-mediated activation of CYP3A4 gene.
2007 May
Assessment of pesticide residues in freshwater areas affected by rice paddy effluents in Southern Japan.
2010 Jan
Temperature, moisture, and fungicide effects in managing Rhizoctonia root and crown rot of sugar beet.
2010 Jul
Evaluation of core cultivation practices to reduce ecological risk of pesticides in runoff from Agrostis palustris.
2010 Jun
Patents

Sample Use Guides

The absorption and metabolism of orally administered flutolanil were investigated in two studies in rats, in which the concentrations of residues in tissues were also determined. No studies of toxicokinetics have been performed in other species. The animals received either a single dose of 20 mg/kg bw [14C]flutolanil; consecutive doses of 20 mg/kg bw per day of unlabelled flutolanil for 14 days followed by single dose of [14C]flutolanil on day 15; or a single dose of 1000 mg/kg [14C]flutolanil.
Route of Administration: Oral
Toxicity of the fungicide Flutolanil was in vitro tested against 20 isolates of Macrophomina phaseolina and cotton seedlings of ten commercial cotton cultivars. The isolates were recovered from roots of cotton plants obtained from different cotton-growing areas in Egypt. Most of the tested isolates were sensitive to Flutolanil; however, they varied in sensitivity. Twenty-five percent of the isolates were highly sensitive where IC50 ranged from < 1 to 5.1 µg/ml, 20% of the isolates were sensitive where IC50 ranged from 15 to 30 µg/ml, 45% of the isolates were moderately sensitive where IC50 ranged from 46 to 58.5 µg/ml, and 10% of the isolates were not much sensitive (tolerant) where IC50 was > 100 µg/ml. Flutolanil was very safe on both shoots and roots of the tested cultivars (IC50 > 100 µg/ml). Treating cotton seeds with Flutolanil resulted in highly significant (P < 0.01) reductions in pathogenicity of 18 isolates and a significant reduction (P < 0.05) in pathogenicity of isolate M29. M1 was the only isolate, which was insensitive to the application of Flutolanil. In vivo toxicity to Flutolanil was not correlated with its in vitro toxicity. However, a highly significant correlation (r = 0.60, P < 0.01) was observed between pathogenicity of isolates and the in vivo toxicity of the fungicide.
Name Type Language
FLUTOLANIL
ISO   MI  
Common Name English
N-(3-(1-METHYLETHOXY)PHENYL)-2-(TRIFLUOROMETHYL)BENZAMIDE
Systematic Name English
FLUTOLANIL [ISO]
Common Name English
FLUTOLANIL [MI]
Common Name English
O-TRIFLUOROMETHYL-M'-ISOPROPOXYBENZOIC ANILIDE
Common Name English
MONCUT
Brand Name English
NNF-136
Code English
PROSTAR
Brand Name English
.ALPHA.,.ALPHA.,.ALPHA.-TRIFLUORO-3'-ISOPROPOXY-O-TOLUANILIDE
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 128975
Created by admin on Fri Dec 15 18:17:12 GMT 2023 , Edited by admin on Fri Dec 15 18:17:12 GMT 2023
Code System Code Type Description
ALANWOOD
flutolanil
Created by admin on Fri Dec 15 18:17:12 GMT 2023 , Edited by admin on Fri Dec 15 18:17:12 GMT 2023
PRIMARY
EPA CompTox
DTXSID8024109
Created by admin on Fri Dec 15 18:17:12 GMT 2023 , Edited by admin on Fri Dec 15 18:17:12 GMT 2023
PRIMARY
MERCK INDEX
m5511
Created by admin on Fri Dec 15 18:17:12 GMT 2023 , Edited by admin on Fri Dec 15 18:17:12 GMT 2023
PRIMARY Merck Index
PUBCHEM
47898
Created by admin on Fri Dec 15 18:17:12 GMT 2023 , Edited by admin on Fri Dec 15 18:17:12 GMT 2023
PRIMARY
CAS
66332-96-5
Created by admin on Fri Dec 15 18:17:12 GMT 2023 , Edited by admin on Fri Dec 15 18:17:12 GMT 2023
PRIMARY
MESH
C475882
Created by admin on Fri Dec 15 18:17:12 GMT 2023 , Edited by admin on Fri Dec 15 18:17:12 GMT 2023
PRIMARY
CHEBI
81792
Created by admin on Fri Dec 15 18:17:12 GMT 2023 , Edited by admin on Fri Dec 15 18:17:12 GMT 2023
PRIMARY
FDA UNII
2USL6Y9JZ4
Created by admin on Fri Dec 15 18:17:12 GMT 2023 , Edited by admin on Fri Dec 15 18:17:12 GMT 2023
PRIMARY