Synthesis and herbicidal activity of 2-acylimino-3-phenyl-1,3-thiazolines—A new family of bleaching herbicides—

Abstract

A novel series of substituted 2-acylimino-1,3-thiazolines was synthesized and their herbicidal activity against upland weeds and selectivity against crops was assessed. The structure-activity relationships were probed by substitution of the thiazoline nucleus and/or an imino group. Highest activity was seen with compounds which contain two substituents: a methyl group at the 5-position of the thiazoline nucleus and a trifluoroacetyl or a difluoroacetyl group on an imino moiety. Among the compounds examined, 2-(N-difluoroacetylimino)-5-methyl-3-(3-trifluoromethylphenyl)-1,3-thiazoline applied at rates between 62.5 and 125 g a.i./ha, showed excellent broadspectrum pre-emergence herbicidal activity against grass and broadleaf weeds without injury to cotton.

Evaluation of the Anti-Schistosoma mansoni Activity of Thiosemicarbazones and Thiazoles

“…Likewise, hydrazones, thiazolidinone, and their bioisoster thiazole derivatives are known for their potential pharmaceutical applications and possess antimicrobial (23), antischistosomal (24), antifungal (25), antimalarial (26), herbicidal (27), antiviral (28), antidiabetic (29), and antioxidant (30) properties. Thiazole derivatives have been used to prepare various drugs that are important for antimicrobial (31), antibacterial (32,33), antifungal (32), antiinflammatory (34), and antitubercular (35) treatment, and some of the thiazole derivatives are used as antiprotozoals (36).…”

Synthesis of 3,4‐Dialkyl‐5‐(1‐oxo‐ethyl)‐3H‐thiazole‐2‐thiones Derivatives and Their Pesticidal Activity

“…The basic 1-(3-alkyl-4-methyl-2-thioxo-2,3-dihydro-thiazol-5-yl)-ethanones 1,2 were synthesized by interaction of N-alkyl-dithiocarbamate sodium salt with 3-chloro-pentane-2,4-dion (Scheme 1). The latter with substituted hidrazines, ureas and thioureas were formed corresponding hydrazones (3,4), ureayl-imino and thioureayl-imino derivatives (5,6). The interaction of ketones 1,2 with hydroxylamine hydrochloride in alkaline solution lead to 1-(3-alkyl-4-methyl-2-thioxo-2,3-dihydro-thiazol-5-yl)-ethanone oximes (7,8) formation.…”

“…By interaction of N-methyl(ethyl)-dithiocarbamate sodium salt with 3-chloro-pentane-2,4-dion the 1-(3-alkyl-4methyl-2-thioxo-2,3-dihydro-thiazol-5-yl)-ethanones 1,2 and corresponding oximes 7,8 were synthesized. On the basis of the mentioned compounds hydrazono (3,4), ureayl and thioureayl (5,6) derivatives, substituted oximes (9,10) and azinyl oximes (11,12) were obtained. The structures of synthesized compounds were confirmed by proton nuclear magnetic resonance spectroscopy and elemental analysis.…”

Synthesis and Biological Study of Some 4‐oxo‐Thiazolidine Derivatives of 2‐Aminothiazole

“…Heterocycles containing thiazolidine moity are of interest because they show some pharmacological and biological activities. Thiazolidines derivatives were reported to possess antifungal, 12,13 antibacterial, antiinflammatory, 14,15 herbicidal, 16 antibiotic agents, 17 antidiabetic 18 and analgesic 19 activities etc. All above biological activities of thiazole and thiazolidine derivatives aroused our attention and promoted us to synthesize a new series of N-[2-{2-(substituted phenyl)-4-oxo-5-(substituted benzylidene)-1,3-thiazolidine}-iminoethyl]-2-aminothiazole, 5a-5m by conventional and microwave methods.…”