Monoterpenoid Isovalerate Esters as Long-Lasting Spatial Mosquito Repellents

Klimavicz, James S.; Corona, Caleb; Norris, Edmund J.; Coats, Joel R.

doi:10.1021/bk-2018-1289.ch011

Cited by 5 publications

(3 citation statements)

References 23 publications

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“…Procedure C. This procedure is adapted from the protocol by Klimavicz et al Aryl amine (1 equiv), carboxylic acid (1.2 equiv), and 4-dimethylaminopyridine (0.15 equiv) were dissolved in dichloromethane (1 mL/mmol) and cooled to 0 °C. N , N ′-Dicyclohexylcarbodiimide (1.05 equiv) in dichloromethane (2 mL/mmol) was added dropwise over 5 min, and the mixture was stirred for 0.25 h at 0 °C.…”

Section: Materials and Methodsmentioning

confidence: 99%

Resistance-Breaking Insecticidal Activity of New Spatial Insecticides against Aedes aegypti

Richoux

Liu

Norris

et al. 2021

J. Agric. Food Chem.

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The use of N-aryl amide derivatives as spatially acting insecticides remains relatively unexplored. To expand this knowledge, we synthesized eighty-nine N-aryl amide analogues and screened them for mortality against an insecticide-susceptible strain of Aedes aegypti mosquitoes, Orlando (OR), using a vapor exposure glass tube assay. Of the screened compounds, twenty-two produced >92% mortality at 24 h and warranted further investigation to determine LC50 values. Fifteen of these analogues had LC50 values within 2 orders of magnitude of transfluthrin, and of significant interest, N-(2,6-dichloro-4-(trifluoromethyl)phenyl)-2,2,3,3,3-pentafluoropropanamide (compound 70) was nearly as potent as transfluthrin and exhibited greater toxicity than metofluthrin when screened against OR A. aegypti. Compounds exhibiting potent toxicity against OR A. aegypti or whose structure–activity relationship potentially offered beneficial insights into structure optimization were screened against the insecticide-resistant, Puerto Rico (PR), strain of A. Aegypti, and it was discovered that not only did these N-arylamides typically show little resistance, some such as N-(2,6-dichloropyridin-4-yl)-2,2,3,3,4,4,4-heptafluorobutanamide (compound 36) and 2,2,3,3,4,4,4-heptafluoro-N-(3,4,5-trifluorophenyl)butanamide (compound 40) were actually more potent against the PR mosquitoes. Due to this promising insecticidal activity, five compounds were administered orally to mice to determine acute oral rodent toxicity. All five compounds were found to have mouse oral toxicity LD50 values well above the minimum safe level as set by the Innovative Vector Control Consortium (50 mg/kg). In addition to the promising biological activity documented here, we report the structure–activity relationship analysis used to guide the derivatization approach taken and to further inform future efforts in the development of N-arylamides as potential resistance-breaking, spatially acting insecticides.

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Section: Materials and Methodsmentioning

confidence: 99%

Resistance-Breaking Insecticidal Activity of New Spatial Insecticides against Aedes aegypti

Richoux

Liu

Norris

et al. 2021

J. Agric. Food Chem.

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“…Small amounts of iso-valeric acid in wine adds a smokey, spicy, or medicinal smell [ 107 ], but an excess of iso-valeric acid in wine is generally seen as a defect, as it can smell sweaty, leathery, or like a barnyard [ 108 ]. Iso-valeric acid is a clear colorless liquid that is a natural volatile fatty acid found in a wide variety of plants and essential oils, which is an important raw material for the production of fragrance iso-valerate [ 109 , 110 ]. Iso-valeric acid is used not only in cheese, baked foods, meat products, and cream/fruit flavors but also in the preparation of medicines, spices, condiments, etc.…”

Section: The Production and Applications Of The Individual Volatile Fatty Acidsmentioning

confidence: 99%

A Glimpse of the World of Volatile Fatty Acids Production and Application: A review

et al. 2022

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Sustainable provision of chemicals and materials is undoubtedly a defining factor in guaranteeing economic, environmental, and social stability of future societies. Among the most sought-after chemical building blocks are volatile fatty acids (VFAs). VFAs such as acetic, propionic, and butyric acids have numerous industrial applications supporting from food and pharmaceuticals industries to wastewater treatment. The fact that VFAs can be produced synthetically from petrochemical derivatives and also through biological routes, for example, anaerobic digestion of organic mixed waste highlights their provision flexibility and sustainability. In this regard, this review presents a detailed overview of the applications associated with petrochemically and biologically generated VFAs, individually or in mixture, in industrial and laboratory scale, conventional and novel applications.

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“…Upon completion, the crude mixture was concentrated under reduced pressure with a rotoevaporator and purified on a silica gel column. Ester synthesis (Scheme 1) utilized an approach 20 where alcohol (1 equiv), carboxylic acid (1.2 equiv), and 4-dimethylaminopyridine (0.15 equiv) were dissolved in dichloromethane (1 mL/mmol) and cooled to 0 °C. N,N′-Dicyclohexylcarbodiimide (1.05 equiv) in dichloromethane (2 mL/mmol) was added dropwise over 5 min, and the mixture was stirred for 0.25 h at 0 °C.…”

Section: ■ Introductionmentioning

confidence: 99%

Structural Exploration of Novel Pyrethroid Esters and Amides for Repellent and Insecticidal Activity against Mosquitoes

Richoux,

Yang,

Norris

et al. 2023

J. Agric. Food Chem.

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The emergence of pyrethroid-resistant mosquitoes is a worldwide problem that necessitates further research into the development of new repellents and insecticides. This study explored the modification of existing pyrethroid acids to identify structural motifs that might not be affected by kdr active site mutations that elicit pyrethroid resistance. Because synthetic pyrethroids almost always contain activity-dependent chiral centers, we chose to focus our efforts on exploring alkoxy moieties of esters obtained with 1R-trans-permethrinic and related acids, which we showed in previous studies to have repellent and/or repellent synergistic properties. To this end, compounds were synthesized and screened for spatially acting repellency and insecticidal activity against the susceptible, Orlando, and pyrethroid-resistant, Puerto Rico, strains of Aedes aegypti mosquito. Screening utilized a highthroughput benchtop glass tube assay, and the compounds screened included a mixture of branched, unbranched, aliphatic, halogenated, cyclic, non-cyclic, and heteroatom-containing esters. Structure−activity relationships indicate that n-propyl, n-butyl, npentyl, cyclobutyl, and cyclopentyl substituents exhibited the most promising repellent activity with minimal kdr cross resistance. Preliminary testing showed that these small alcohol esters can be synergistic with phenyl amides and pyrethroid acids. Further derivatization of pyrethroid acids offer an interesting route to future active compounds, and while mosquitoes were the focus of this work, pyrethroid acids and esters have potential for use in reducing pest populations and damage in cropping systems as well.

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Monoterpenoid Isovalerate Esters as Long-Lasting Spatial Mosquito Repellents

Cited by 5 publications

References 23 publications

Resistance-Breaking Insecticidal Activity of New Spatial Insecticides against Aedes aegypti

Resistance-Breaking Insecticidal Activity of New Spatial Insecticides against Aedes aegypti

A Glimpse of the World of Volatile Fatty Acids Production and Application: A review

Structural Exploration of Novel Pyrethroid Esters and Amides for Repellent and Insecticidal Activity against Mosquitoes

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