Insecticidal, repellent and fungicidal properties of novel trifluoromethylphenyl amides
| Autor: | Daniel R. Swale, Jeffrey R. Bloomquist, Maia Tsikolia, Monique R. Coy, Natasha M. Agramonte, James J. Becnel, Katelyn C. Chalaire, Kenneth J. Linthicum, Gary G. Clark, Ulrich R. Bernier, David E. Wedge, Nurhayat Tabanca |
|---|---|
| Rok vydání: | 2013 |
| Předmět: |
Insecticides
animal structures Health Toxicology and Mutagenesis Aedes aegypti Plant pathogenic fungi Medicinal chemistry DEET Lethal Dose 50 chemistry.chemical_compound Anopheles albimanus Trifluoromethylphenyl amides Aedes Organic chemistry Animals Pesticides Fipronil Trifluoromethyl biology fungi Fungi General Medicine Pesticide biology.organism_classification Amides Fungicides Industrial Fungicide Drosophila melanogaster chemistry Insect Repellents Larva Drosophila Female Agronomy and Crop Science |
| Zdroj: | Pesticide Biochemistry and Physiology. 107(1):138-147 |
| ISSN: | 0048-3575 |
| DOI: | 10.1016/j.pestbp.2013.06.006 |
| Popis: | Twenty trifluoromethylphenyl amides were synthesized and evaluated as fungicides and as mosquito toxicants and repellents. Against Aedes aegypti larvae, N-(2,6-dichloro-4-(trifluoromethyl)phenyl)-3,5-dinitrobenzamide (1e) was the most toxic compound (24 h LC50 1940 nM), while against adults N-(2,6-dichloro-4-(trifluoromethyl)phenyl)-2,2,2-trifluoroacetamide (1c) was most active (24 h LD50 19.182 nM, 0.5 μL/insect). However, the 24 h LC50 and LD50 values of fipronil against Ae. aegypti larvae and adults were significantly lower: 13.55 nM and 0.787 × 10(-4) nM, respectively. Compound 1c was also active against Drosophila melanogaster adults with 24 h LC50 values of 5.6 and 4.9 μg/cm(2) for the Oregon-R and 1675 strains, respectively. Fipronil had LC50 values of 0.004 and 0.017 μg/cm(2) against the two strains of D. melanogaster, respectively. In repellency bioassays against female Ae. aegypti, 2,2,2-trifluoro-N-(2-(trifluoromethyl)phenyl)acetamide (4c) had the highest repellent potency with a minimum effective dosage (MED) of 0.039 μmol/cm(2) compared to DEET (MED of 0.091 μmol/cm(2)). Compound N-(2-(trifluoromethyl)phenyl)hexanamide (4a) had an MED of 0.091 μmol/cm(2) which was comparable to DEET. Compound 4c was the most potent fungicide against Phomopsis obscurans. Several trends were discerned between the structural configuration of these molecules and the effect of structural changes on toxicity and repellency. Para- or meta- trifluoromethylphenyl amides with an aromatic ring attached to the carbonyl carbon showed higher toxicity against Ae. aegypti larvae, than ortho- trifluoromethylphenyl amides. Ortho- trifluoromethylphenyl amides with trifluoromethyl or alkyl group attached to the carbonyl carbon produced higher repellent activity against female Ae. aegypti and Anopheles albimanus than meta- or para- trifluoromethylphenyl amides. The presence of 2,6-dichloro- substitution on the phenyl ring of the amide had an influence on larvicidal and repellent activity of para- trifluoromethylphenyl amides. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect