Synthesis of Novel Pesticidal N,N′-Disubstituted Sulfamide Derivatives Using Sulfur(VI) Fluorine Exchange Click Reaction

Abstract

Sulfur(VI) fluorine exchange click reaction was applied to the highly efficient synthesis of new N,N′-disubstituted sulfamide (R 1 NH−SO 2 −NHR 2 ) derivatives as pesticide candidates. Bioassays were conducted to evaluate both insecticidal and fungicidal activities of the target compounds. Preliminary results showed that the target molecules exhibited good bioactivities. In particular, insecticidal activities of compounds D25 and D21 against Plutella xylostella (LC 50 = 2.42 and 3.87 μg•mL −1 ) were superior or adequate to that of commercial insecticide indoxacarb (LC 50 = 3.99 μg•mL −1 ). Moreover, some compounds could also exhibit satisfactory fungicidal activity toward plant pathogens Pyricularia grisea, Botrytis cinerea, and Thanatephorus cucumeris. This work could bring new insights into the application of heterocyclic N,N′-disubstituted sulfamides as novel pesticides.

Palladium-Catalyzed Direct Synthesis and Insecticidal Activity of Arylmatrine Derivatives

“…This work commenced with the direct preparation of arylated analogues of matrine (1a−19a and 1b−19b) via Pd-catalyzed cross-coupling reactions with various aryl bromides (1−19). Initially, the reaction conditions were optimized using as a coupling partner bromobenzene (1).…”

“…Column chromatography was carried out using silica gel H (Qingdao Sea Chemical Factory, Qingdao, People's Republic of China) under pressure. 1 H and 13 C NMR spectra were recorded in CDCl 3 at ambient temperature on a Bruker AV 600 nuclear magnetic resonance instrument. Chemical shifts were recorded in ppm relative to tetramethylsilane as the internal standard.…”

“…I nsect pests seriously endanger food security, causing both quality loss and yield reduction in agricultural production worldwide. 1 To date, many strategies, including biological control and chemical control, have been exploited to avoid pest attack on crops. 2 However, long-term repeated or irrational use of existing pesticides has led to drug resistance of pests, accompanied by serious environmental problems.…”

“…Insect pests seriously endanger food security, causing both quality loss and yield reduction in agricultural production worldwide . To date, many strategies, including biological control and chemical control, have been exploited to avoid pest attack on crops .…”

Synthesis and Anti‐Fungal/Oomycete Activity of Novel Sulfonamide Derivatives Containing Camphor Scaffold

“…[16 -18] For crop protection, amisulbrom, chesulfamide, cyazofamid and N,N-disubstituted sulfamides have been utilized as fungicides to treat various fungal diseases. [19][20][21] On the other hand, diaryl ether moiety can be observed in many herbicides and fungicides. [22] For example, one novel succinate dehydrogenase inhibitor (SDHI), flubeneteram have been commercialized in 2021, which demonstrated excellent protective activity toward Rhizoctonia solani and Fusarium graminearum.…”