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
SMILES
CC(C)OC1=CC(NC(=O)C2=CC=CC=C2C(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)
| 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.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays. | 2011-02-27 |
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| Flutolanil [N-(3-isopropoxyphen-yl)-2-(trifluoro-meth-yl)benzamide]. | 2010-09-04 |
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| Temperature, moisture, and fungicide effects in managing Rhizoctonia root and crown rot of sugar beet. | 2010-07 |
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| Evaluation of core cultivation practices to reduce ecological risk of pesticides in runoff from Agrostis palustris. | 2010-06 |
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| Pesticide transport with runoff from creeping bentgrass turf: Relationship of pesticide properties to mass transport. | 2010-06 |
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| Impact of environmental chemicals on key transcription regulators and correlation to toxicity end points within EPA's ToxCast program. | 2010-03-15 |
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| Pesticide residues in coastal waters affected by rice paddy effluents temporarily stored in a wastewater reservoir in southern Japan. | 2010-02 |
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| Assessment of pesticide residues in freshwater areas affected by rice paddy effluents in Southern Japan. | 2010-01 |
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| Toxicity of agricultural chemicals in Daphnia magna. | 2009-12 |
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| Pesticide transport with runoff from turf: observations compared with TurfPQ model simulations. | 2009-10-31 |
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| Crystallization of mitochondrial rhodoquinol-fumarate reductase from the parasitic nematode Ascaris suum with the specific inhibitor flutolanil. | 2009-09-01 |
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| Daily variation of pesticides in surface water of a small river flowing through paddy field area. | 2009-06 |
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| Pesticides in water and sediment from littoral area of Lake Biwa. | 2009-06 |
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| Investigation of the estrogenic activities of pesticides from Pal-dang reservoir by in vitro assay. | 2007-12-15 |
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| Assessment of human pregnane X receptor involvement in pesticide-mediated activation of CYP3A4 gene. | 2007-05 |
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| Flutolanil and carboxin resistance in Coprinus cinereus conferred by a mutation in the cytochrome b560 subunit of succinate dehydrogenase complex (Complex II). | 2004-10 |
|
| Bioassay of various pesticides by microcalorimetry measuring the metabolic heat of yeast. | 2004 |
|
| Pesticide exposure in dwellings near bulb growing fields in The Netherlands: an explorative study. | 2004 |
|
| [Effects of rice cleaning and cooking process on the residues of flutolanil, fenobucarb, silafluofen and buprofezin in rice]. | 2003-02 |
|
| The effects of fungicides on the phylloplane yeast populations of creeping bentgrass. | 2002-06 |
|
| Integrated biological and chemical control of damping-off caused by Rhizoctonia solani using Bacillus subtilis RB14-C and flutolanil. | 2001 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24039478
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
Edited
Mon Mar 31 19:09:12 GMT 2025
by
admin
on
Mon Mar 31 19:09:12 GMT 2025
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| Record UNII |
2USL6Y9JZ4
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| Record Status |
Validated (UNII)
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| Record Version |
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EPA PESTICIDE CODE |
128975
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admin on Mon Mar 31 19:09:12 GMT 2025 , Edited by admin on Mon Mar 31 19:09:12 GMT 2025
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flutolanil
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DTXSID8024109
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m5511
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47898
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66332-96-5
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C475882
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81792
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2USL6Y9JZ4
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