Synthesis and biological potency of anilino‐triazine insecticides

Johnson, Timothy C.; Brown, Annette Vitale; Bryan, Kristy K; Guenthenspberger, Katherine K; Hunter, Ricky; Martín, Timothy; Niyaz, Noormohamed M.; Tisdell, Gene F; Trullinger, Tony K.

doi:10.1002/ps.4593

Cited by 1 publication

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References 7 publications

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“…The diet assays for biological testing used insects supplied from in‐house colonies maintained at Corteva Agriscience™ (Indianapolis, IN, USA). Primary and secondary insecticidal screening was performed as previously described . Pure active ingredients were used for all diet assays.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, stability and insecticidal activity of 2‐arylstilbenes

Horty

Daeuble

Castetter

et al. 2019

Pest Management Science

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BACKGROUND: A chemical scaffold-hopping approach from known 3-hydroxyl-3-methylglutaryl-CoA (HMG-CoA) reductase inhibitors identified (E/Z)-2-arylstilbenes as novel insecticidal hits against two lepidopteran species, Spodoptera exigua and Trichoplusia ni. A structure-activity relationship (SAR) study of the aryl substituents and the E/Z conformations was carried out in an effort to improve insecticidal potency. RESULTS:A series of (E/Z)-2-arylstilbenes was prepared and separated to evaluate their insecticidal potency against lepidopterous species in diet-feeding assays. The results showed that the (Z)-2-arylstilbenes were more active than their corresponding (E)-isomers, and a stereoselective synthesis was utilized to expand the SAR of the (Z)-2-arylstilbenes. (Z)-4'-Fluoro-3 ′ -methyl-2-(2,4-difluorostyryl)-4-fluoro-5-methoxy-1,1 ′ -biphenyl was the most potent analog in this study with strong activity against S. exigua, T. ni, Helicoverpa zea, Plutella xylostella and Pseudoplusia includens.CONCLUSION: The (Z)-2-arylstilbenes were found to have strong insecticidal potency against five lepidopteran species. Ultimately, synthetic efforts could not improve insecticidal potency to commercial levels, and a lack of UV stability led to efforts being discontinued.

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Section: Methodsmentioning

confidence: 99%