Studies toward understanding the<scp>SAR</scp>around the sulfoximine moiety of the sap‐feeding insecticide sulfoxaflor

Buysse, Ann; Nugent, Benjamin M.; Wang, Nick X.; Benkő, Zoltán; Breaux, Nneka; Rogers, Richard B.; Zhu, Yujie

doi:10.1002/ps.4351

Cited by 10 publications

(13 citation statements)

References 20 publications

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“…Insecticide bioassays on M. persicae were conducted as previously described. 10 blank, and were replicated four to six times. Treated plants were held at 26 ∘ C, with a 16:8 h light/dark photoperiod.…”

Section: Myzus Persicae Bioassaymentioning

confidence: 99%

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Discovery of novel insecticidal 3‐aminopyridyl ureas

Lambert

Buysse

Wessels

2019

Pest Management Science

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BACKGROUND: Commercial compound databases represent rich sources of potential starting points for pharmaceutical and agrochemical product development. Routine insecticidal screening of compounds ordered from these sources led to the identification of a 3-aminopyridyl urea with activity against Myzus persicae (Sulzer) (green peach aphid). Based on this activity and its structural novelty, further exploration of the chemical space around this hit was initiated. RESULTS:A series of ureas based on the structure of the initial hit were synthesized and screened for insecticidal activity. A broad range of tail groups derived from cyclic secondary amines were explored, and many of these compounds were found to be insecticidally active. However, only compounds featuring a 3-aminopyridine or 4-aminopyridazine head group exhibited significant insecticidal potency. Although activity against M. persicae was consistently observed, these ureas were largely inactive against another key sap-feeding insect pest, Bemisia tabaci (Glennadius) (sweetpotato whitefly). CONCLUSIONS: Follow-up of an insecticide hit identified from commercial compound acquisition led to the discovery of a novel class of ureas with activity against M. persicae. Despite considerable effort to identify related compounds with additional insecticidal spectrum, however, activity on other important pests remains limited. WT Lambert, AM Buysse, FJ Wessels 2.1.13 4-(Cyclopropylmethyl)-3-oxo-N-(pyridin-3-yl)piperazine-1carboxamide (22) The title compound (95.8 mg, 27% yield) was isolated as an off-white solid: m.p. 172-175 ∘ C; 1 H NMR (400 MHz, CDCl 3 ) 8.67 (d, J = 2.4 Hz, 1H), 8.28 (dd, J = 4.7, 1.4 Hz, 1H), 8.04 (ddd, J = 8.4, Pest Manag Sci 2020; 76: 497-508

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Section: Myzus Persicae Bioassaymentioning

confidence: 99%

“…Because 3-substituted pyridines are ubiquitous among commercial sap-feeding insecticides, we opted to explore this substructure further. Relevant examples of 3-pyridyl-containing insecticides include afidopyropen, 5 pymetrozine, 6 imidacloprid, 7 flupyradifurone, 8 flonicamid, 9 and sulfoxaflor 10 (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Discovery of novel insecticidal 3‐aminopyridyl ureas

Lambert

Buysse

Wessels

2019

Pest Management Science

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“…The next article also focuses on SAR studies, but in a much more advanced project. Nugent et al (Dow AgroSciences) detail their efforts around the sap‐feeding insecticide sulfoxaflor. In particular, this article focuses on the optimization and SAR around the sulfoximine moiety.…”

Section: Research Articlesmentioning

confidence: 99%

Innovations in Agrochemical Discovery and the Role of Metabolism, Bioavailability and Formulations

Lorsbach¹,

Sparks²

2017

Pest Management Science

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“…The research on sulfoxaflor mainly focused on the sulfoximine group [7,9] and lack the studies on the pyridine moiety. Meanwhile, the antifungal activity of sulfoximine compounds was hardly reported.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, and biological activity of sulfoximine derivatives

Liu

Wang

Yong

et al. 2021

Journal of Heterocyclic Chem

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In order to discover new pesticides with novel modes of action and further study the sulfoximine scaffolds, 30 novel sulfoximine derivatives were designed, synthesized, and evaluated for their insecticidal and antifungal activities. The preliminary bioassay results showed that the insecticidal activity of target compounds was weak, only I-12 displayed 80.39% larvicidal activity against Nilaparvata lugen, slightly lower than sulfoxaflor (97.87%) at 100 μg/ml. However, most of the compounds also displayed fair to good fungicidal activities against eight representative phytopathogenic fungi, and I-5 showed slightly lower fungicidal activity against Sclerotinia scleotiorum than the control drug difenoconazole (2.26 μg/ml) with an EC 50 of 8.75 μg/ml. The structure-activity relationship showed that the compound exhibited better antifungal activity when the R was 2.4-disubstituted phenyl. Our studies suggested that sulfoximine scaffolds may also have potential plant-fungal activity. This is the first report on the use of sulfoximide scaffolds as fungicides.

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Studies toward understanding theSARaround the sulfoximine moiety of the sap‐feeding insecticide sulfoxaflor

Cited by 10 publications

References 20 publications

Discovery of novel insecticidal 3‐aminopyridyl ureas

Discovery of novel insecticidal 3‐aminopyridyl ureas

Innovations in Agrochemical Discovery and the Role of Metabolism, Bioavailability and Formulations

Design, synthesis, and biological activity of sulfoximine derivatives

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