N-PERFLUOROALKANESULFONYL SULFILIMINES:SYNTHESIS AND X-RAY STRUCTURE ANALYSIS

N-Perfluoroalkanesulfonyl S,S-dialkyl sulfilimines R_fSO_2N=SR^1R^2 were prepared in high yields by condensation of N-sulfinylperfluoroalkane- sulfonamides R_fSO_2NSO with sulfones.The X-ray structrue analysis of R_fSO_2N=SMe_2 shows that the S^IVNs^VI group contains a delocalized d-π bond system.

Design, Synthesis, Structure-Activity Relationship and Insecticidal Activities of Trifluoromethyl-Containing Sulfiliminyl and Sulfoximinyl Phthalic Acid Diamide Structure

Due to a novel mode action,low toxicity to mammals and low residue characteristics,phthalic acid diamides have aroused considerable interests in agricultural chemistry.With introduction of N-cyano,N-trifluoroacetyl,N-carbamoylsulfiliminyl and sulfoximinyl substituents into phthalamides,12 novel derivatives containing trifluoromethyl moiety were designed and synthesized.All title compounds were characterized by ^(1)H NMR and high-resolution mass spectrometry.The preliminary results of biological activity assessment indicated that some title compounds exhibited moderate to good insecticidal activities against oriental armyworm(Pseudaletia separata Walker).In particular,Va gave higher activity against oriental armyworm and diamondback moth.The present work reported that the new trifluoromethylated diamides incorporating N-trifluoroacetylsulfoximinyl moieties are potential lead compounds for further structure optimization,providing some insight into the relating structure-activity relationship.

The exploration of chiral N-cyano sulfiliminyl dicarboxamides on insecticidal activities

Due to new mechanism of action and ecofriendly characteristics,dicarboxamide insecticides have attracted more and more attentions in modern pest management.A series of 20 dual chiral N-cyano sulfilimines containing two centers（carbon and sulfur） were designed and synthesized.All title compounds were determined by ^1H NMR,high-resolution mass spectrometry（HRMS） and optical polarimeter.The preliminary results indicated that some of them exhibited favourable insecticidal activities against oriental armyworm（Pseudaletia separata Walker）.These isomers exhibited different impact on activity following the sequence as（Sc,Ss） 〉（Sc,Rs）,and the rule of title compounds＇ activity against oriental armyworm was 3-CF3≥2—CH3—4—Cl〉2,3,4-trifluro in the anilide moiety.The results indicated that these groups such as 3-CF3,2—CH3—4—Cl or 2,3,4-trifluro were inefficient to replace heptafluoroisopropyl group for high larvicidal activity,which provided some guidance for the further modifications of sulfiliminyl dicarboxamides.

Hydrogen selenide,a vital metabolite of sodium selenite,uncouples the sulfilimine bond and promotes the reversal of liver fibrosis

Sodium selenite has alleviating effects on liver fibrosis;however,its therapeutic molecular mechanism remains unclear.Herein,hydrogen selenide,a major metabolite of Na_(2)SeO_(3),was tested to uncouple the sulfilimine bond in collagen IV,the biomarker of liver fibrosis.A mouse model of liver fibrosis was constructed via a CCl_(4)-induced method,followed by the administration of 0.2 mg kg−1 Na_(2)SeO_(3)via gavage three times per week for 4 weeks.Changes in H2Se,NADPH,and H_(2)O_(2)levels were monitored in real time by using NIR-H2Se,DCI-MQ-NADPH,and H_(2)O_(2)probes in vivo,respectively.H_(2)Se continuously accumulated in the liver throughout the Na_(2)SeO_(3)treatment period,but the levels of NADPH and H_(2)O_(2)decreased.The expression of collagen IV was analyzed through Western blot and liquid chromatography-mass spectrometry.Results confirmed that the sulfilimine bond of collagen IV in the fibrotic mouse livers could be broken by H2Se with the Na_(2)SeO_(3)treatment.Therefore,the therapeutic effect of Na_(2)SeO_(3)on liver fibrosis could be mainly attributed to H_(2)Se that uncoupled the sulfilimine bond to induce collagen IV degradation.This study provided a reasonable explanation for the molecular mechanism of the in vivo function of Na_(2)SeO_(3)and the prevention of liver fibrosis by administering inorganic selenium.