Synthesis and Herbicidal Evaluation of Novel Uracil Derivatives Containing Benzothiazol‐2‐yl Moiety

Abstract

In order to search for novel Protox inhibitors with high efficiency, broad‐spectrum activity, and safety to crops, commercially herbicide butafenacil was used as lead compound for further optimization, a series of title compounds 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i were designed and synthesized by introducing benzothiazol‐2‐yl moiety into the uracil skeleton. The bioassays indicated that some of the target compounds displayed moderate herbicidal activities in the post‐emergence treatment.

Modern Approaches to the Synthesis and Transformations of Practically Valuable Benzothiazole Derivatives

“…They also possess antimicrobial [ 14 , 15 , 16 , 17 , 18 , 19 , 20 ], antioxidant [ 20 ], anti-inflammatory [ 21 , 22 , 23 , 24 ], analgesic [ 24 ], antidepressant [ 25 , 26 ], anticonvulsant [ 27 , 28 , 29 ], anti-diabetic [ 21 , 30 ], antitumor [ 31 , 32 , 33 , 34 , 35 ], antituberculosis [ 14 , 36 ] activity. Their derivatives show also antimalarial [ 37 , 38 ], insecticide [ 39 ] and herbicide effect [ 40 ]. They are also used as key intermediates in fine organic synthesis and the resins’ components [ 41 ].…”

“…The ring-substituted 2-aminobenzothiazoles formed in situ from diaminodiaryl disulfides enter the three-component domino reaction, which includes diacylation of diaminodiaryl disulfide, oxidative S-cyanation by CuCN, cyclization via nucleophilic attack of the thiocyanate carbon atom and, finally, intermolecular acyl group migration to the exocyclic nitrogen atom (Scheme 12) [54]. Acylation of 6-substituted 2-aminobenzothiazoles by polysubstituted benzoic acids containing the uracil moiety affords benzamides 13a-i possessing herbicide activity (Scheme 13) [40]. Scheme 13.…”

“…Acylation of 6-substituted 2-aminobenzothiazoles by polysubstituted benzoic acids containing the uracil moiety affords benzamides 13a-i possessing herbicide activity (Scheme 13) [40]. Scheme 13.…”

Utility of 6-Aminouracils for Building Substituted and Heteroannulated Pyrimidines: A Comprehensive Review

“…1,2 Uracil (pyrimidine-2,4(1H,3H)-dione) is a common and naturally occurring pyrimidine derivative and represents one of the four nucleobases in the nucleic acid (RNA). 3 Numerous derivatives of uracil have incredible utility in biology and in medicinal chemistry 4 such as anticancer, 5 antitumor, 6 antineoplastic, 7 antiprotozoal, 8 anti-HIV, 9 anti-HCMV, 10 antitubercular, 11 antiviral, 12 antifungal, 13 antibacterial, 14 insecticidal, 15 herbicidal, 16 and antimicrobial activities. 17 Azo-uracils have been used as hypotonic drugs.…”

Synthesis of biologically active derivatives of 2-aminobenzothiazole

“…1 Molecules with a benzothiazole moiety have a pronounced spectrum of biological activity, exhibiting, along with antiviral, 2 – 5 also antimicrobial, 6 – 10 anti-inflammatory, 10 – 15 antidiabetic, 14 analgesic, 12 , 13 antioxidant, 6 , 14 , 15 antidepressant, 16 anticonvulsant, 17 , 18 antianginal, 19 antitumor, 20 , 21 immunomodulatory effects. BTA derivatives also have anthelmintic, 6 , 7 antimalarial, 23 fungicidal, 6 , 24 insecticidal, 24 , 25 and herbicidal 26 effects.…”