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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

Molecular Formula C17H16F3NO2
Molecular Weight 323.3096
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Bioassay of various pesticides by microcalorimetry measuring the metabolic heat of yeast.
2004
Flutolanil and carboxin resistance in Coprinus cinereus conferred by a mutation in the cytochrome b560 subunit of succinate dehydrogenase complex (Complex II).
2004 Oct
Investigation of the estrogenic activities of pesticides from Pal-dang reservoir by in vitro assay.
2007 Dec 15
Pesticides in water and sediment from littoral area of Lake Biwa.
2009 Jun
Crystallization of mitochondrial rhodoquinol-fumarate reductase from the parasitic nematode Ascaris suum with the specific inhibitor flutolanil.
2009 Sep 1
Evaluation of core cultivation practices to reduce ecological risk of pesticides in runoff from Agrostis palustris.
2010 Jun
Impact of environmental chemicals on key transcription regulators and correlation to toxicity end points within EPA's ToxCast program.
2010 Mar 15
Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays.
2011 Feb 27
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:17:12 UTC 2023
Edited
by admin
on Fri Dec 15 18:17:12 UTC 2023
Record UNII
2USL6Y9JZ4
Record Status Validated (UNII)
Record Version
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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 UTC 2023 , Edited by admin on Fri Dec 15 18:17:12 UTC 2023
Code System Code Type Description
ALANWOOD
flutolanil
Created by admin on Fri Dec 15 18:17:12 UTC 2023 , Edited by admin on Fri Dec 15 18:17:12 UTC 2023
PRIMARY
EPA CompTox
DTXSID8024109
Created by admin on Fri Dec 15 18:17:12 UTC 2023 , Edited by admin on Fri Dec 15 18:17:12 UTC 2023
PRIMARY
MERCK INDEX
m5511
Created by admin on Fri Dec 15 18:17:12 UTC 2023 , Edited by admin on Fri Dec 15 18:17:12 UTC 2023
PRIMARY Merck Index
PUBCHEM
47898
Created by admin on Fri Dec 15 18:17:12 UTC 2023 , Edited by admin on Fri Dec 15 18:17:12 UTC 2023
PRIMARY
CAS
66332-96-5
Created by admin on Fri Dec 15 18:17:12 UTC 2023 , Edited by admin on Fri Dec 15 18:17:12 UTC 2023
PRIMARY
MESH
C475882
Created by admin on Fri Dec 15 18:17:12 UTC 2023 , Edited by admin on Fri Dec 15 18:17:12 UTC 2023
PRIMARY
CHEBI
81792
Created by admin on Fri Dec 15 18:17:12 UTC 2023 , Edited by admin on Fri Dec 15 18:17:12 UTC 2023
PRIMARY
FDA UNII
2USL6Y9JZ4
Created by admin on Fri Dec 15 18:17:12 UTC 2023 , Edited by admin on Fri Dec 15 18:17:12 UTC 2023
PRIMARY