Design, synthesis, insecticidal, and acaricidal activities of novel pyrimidinamine derivatives containing a biphenyl ether

Abstract

A series of original pyrimidinamine derivatives containing a biphenyl ether moiety were designed and synthesized. Their structures were confirmed by 1H NMR, MS, and elemental analyses. Their insecticidal activities against lepidopteran and hemiptera insects and acaricidal activities were tested. The results of bioassay demonstrated that 9k showed the best activity (LC50 = 2.08 mg/L) against Tetranychus urticae, which is comparable with the positive control, spirotetramat (LC50 = 2.27 mg/L), and 9g showed better activity (LC50 = 0.52 mg/L) against Aphis fabae than the positive control, imidacloprid (LC50 = 1.02 mg/L), and relatively good activity (LC50 = 2.49 mg/L) against T urticae. Their structure‐activity relationships indicated that both an ethyl group on the 4‐position of the pyrimidine ring and alkyl chain as a para‐substituent group of the benzene ring showed good biological activity.

Synthesis and herbicidal activity of pyrimidyl‐1,2,4‐triazole derivatives containing aryl sulfonyl moiety

“…For over a century, pyrimidines have drawn considerable attention owing to their wide distribution in nature [1]. Pyrimidine derivatives incorporating functional groups at the 2‐, 4‐, 5‐, and 6‐positions have been found to display diverse bioactivities, such as antimicrobial [2], antifungal [3], insecticidal [4], herbicidal [5,6], and plant growth regulating [7]. To date, numerous commercial pyrimidine herbicides have been employed worldwide in croplands [8].…”

Synthesis and Antifungal and Insecticidal Activities of Novel N-Phenylbenzamide Derivatives Bearing a Trifluoromethylpyrimidine Moiety

“…Plant fungal diseases and insect pests have drawn widespread attention because of their enormous damage toward agriculture [14]. e traditional commercial fungicides and insecticides used to prevent and control plant diseases could increase the yield, improve the quality of agricultural products, and also not reduced huge loss annually [5,6].…”

“…Pyrimidine is one of best important chemical scaffolds for application in pesticide chemistry, medicinal chemistry, and material chemistry. Many of pyrimidine derivatives play an important role of bioactive compounds, such as antifungal [9,10], antibacterial [11,12], acaricidal [13,14] insecticidal [15,16], herbicidal [17,18], and antiviral [19,20] activities. Meanwhile, N-phenylbenzamide, a key active fragment in pesticide chemistry, is usually used as a pesticide active fragment and exhibit extensive biological activities, such as antiviral, antifungal, antibacterial, herbicidal, and insecticidal activities [21].…”

Design, Synthesis, and Structure–Activity Relationship of Novel Spiropyrimidinamines as Fungicides against Pseudoperonospora cubensis

“…Zhang et al showed that pyrimidinamine derivatives containing phenyloxazole had remarkable insecticidal activity against Aphis fabae . Li et al disclosed that pyrimidinamine derivatives containing a biphenyl ether displayed good insecticidal activity against Tetranychus urticae . In our previous study, a new pyrimidinamine derivative containing an aryloxy pyridine moiety was delivered by replacing the benzene ring of diflumetorim with an aryloxy pyridine as a promising candidate for control of Plasmopara viticola .…”