Synthesis and phytotoxic activity of novel acylthiourea and 2H-1,2,4-thiadiazolo[2,3-.ALPHA.]pyrimidine derivatives

Abstract

Eight N- [3-(2,4-dichlorophenyl)-5-methylisoxazol-4-ylcarbonyl]-N′-(4,6-disubstituted pyrimidin-2-yl)thioureas and eight 5,7-disubstituted-2-[3-(2,4-dichlorophenyl)-5-methyl isoxazol-4-ylcarbonylimino]-2H-1,2,4-thiadiazolo[2,3-α]pyrimidines were synthesized by multi-step reactions in yields of 50-85%. The structures of the target compounds were confirmed by IR, 1 H NMR spectra and elemental analyses. Phytotoxic activities against Echinochloa crus-galli L., Digitaria ciliaris L., Brassica napus L. and Chenopodium serotinum L. were evaluated by the culture dish method. Preliminary bioassay results indicated that some target compounds exhibited good phytotoxic activity at a dose of 100 mg/L, with an inhibitory rate of 76.0-85.6% on root growth, even higher than the control herbicide, fenoxaprop-P-ethyl.

A review on the chemistry, coordination, structure and biological properties of 1-(acyl/aroyl)-3-(substituted) thioureas

“…[343] Their insecticidal activities against oriental armyworm (Mythimna separata), mosquito larvae (Culex pipiens pallens) and diamondback moth (Plutella xylostella) were evaluated and indicated that the introduction of the 1-(acyl) thiourea group into some structures is important for retention of insecticidal activity. [343] N- [3-(2,4-dichlorophenyl)-5-methylisoxazol-4-ylcarbonyl]-N -(4,6-di-substituted pyrimidin-2-yl)thioureas [344] exhibit good phytotoxic activity against Echinochloa crusgalli L., Digitaria ciliaris L., Brassica napus L. and Chenopodium serotinum L.…”

Steroidal[17,16-d]pyrimidines derived from dehydroepiandrosterone: A convenient synthesis, antiproliferation activity, structure-activity relationships, and role of heterocyclic moiety

“…It is well known that pyrimidine core has wide occurrence in nature 4 , and which has also represent a typical class of heterocyclic scaffold in various compounds applied in the field of medicinal chemistry 5 6 7 8 9 10 11 12 13 14 15 , agrochemicals 16 17 18 19 20 21 22 23 24 , and materials 25 26 27 28 29 . Up to now, many pyrimidines analogues have been demonstrated to exhibit wide pharmacological activities mainly including anticancer, antiviral, antibacterial, antimalarial, antituberculosis activities.…”

A Convenient Synthesis and Biological Research of Novel 5,6,7,8‐Tetrahydro‐1,6‐naphthyridin‐2(1H)‐one Derivatives Hydrochloride as Cytotoxic Agents

“…Nitrogen is the most favorite heteroelement in life science research, and heterocyclic compounds containing N attract great interest of the researchers . Naphthyridine is an important member of N‐containing compounds, and its derivatives have gained special attention of researchers on account of their variety of interesting biological activities in medicinal chemistry.…”