Development of Agrochemicals Regulating Metamorphosis and Diapause

保幼激素（JH）和蜕皮激素参与昆虫的变态、生殖和胚胎发生、滞育、行为等多种生理功能，具有抗JH和抗蜕皮激素活性的化合物，即昆虫生长调节剂，为昆虫的选择性控制提供了一种有前景的方法，也为昆虫的生理生化研究提供了一种有效的工具。本研究旨在设计合成一系列新型的昆虫生长调节剂。各种1，5-二取代咪唑抑制体外JH III生物合成在离体咽侧体从蟑螂，Diploptera punctata，并引起了显着的积累的甲基法尼酸，这表明抑制甲基法尼酸环氧酶。在所测试的化合物中，1-异丁基-5-（3-苄氧基苯基）-咪唑显示出最高的活性。大量的1-取代咪唑和3-吡啶基醚以及1，5-二取代咪唑诱导早熟 ...更多信息 家蚕幼虫的变态过程。这些化合物引起早熟化蛹的活性被同时应用的虫酰肼（一种非甾体蜕皮甾类激动剂）完全抵消，表明这些化合物暂时抑制幼虫血淋巴中的蜕皮甾类滴度以诱导早熟化蛹。已发现多种1，5-二取代咪唑类化合物对褐稻虱、褐飞虱和灰飞虱的幼虫具有延迟毒力。在所测试的一系列化合物中，1-异丁基-和1-新戊基-5-（3-三氟乙氧基苯基）咪唑显示出最高的活性。1-取代咪唑类终止了天蚕（Antheraea yamai）pharate一龄幼虫的滞育。1-[5-（4-乙基苯氧基）戊基]咪唑显示出与KK-42相当的活性，KK-42是迄今为止最有效的化合物。将KK-42注射到预定产生滞育卵的家蚕（Daizo品系）的五龄幼虫中，诱导蛾产生非滞育卵。少

Since juvenile hormone (JH) and ecdysteroids are involved in many physiological functions in insects such as metamorphosis, reproductive and embryogenic events, diapause, and behavior, compounds with anti-JH and anti-ecdysteroid activity, insect growth regulators, offer a prospective method for selective insect control as well as an effective tool in studies of insect biochemistry and physiology. In this research project, the design and synthesis of a novel series of insect growth regulators were carried out. Various 1,5-disubstituted imidazoles inhibited in vitro JH III biosynthesis in isolated corpora allata from the cockroach, Diploptera punctata, and caused a significant accumulation of methyl farnesoate, suggesting an inhibition of methyl farnesoate epoxidase. Among the compounds tested, 1-Isobutyl-5-(3-benzyloxyphenyl)-imidazole showed the highest activity. A large number of 1-substituted imidazoles and 3-pyridyl etheres as well as 1,5-disubstituted imidazoles induced precocious … More metamorphosis in the larvae of the silkworm, Bombyxmori. The activity of these compounds to cause precocious pupation was completely counteracted by the simultaneous application of tebufenozide, a non-steroidal ecdysteroid agonist, indicating that these compounds temporarily depressed the ecdysteroid titer in the larval hemolymph to induce precocious pupation. A variety of 1,5-disubstituted imidazoles-have been found to show delayd toxicity against the larvae of the brown rice planthopper, Nilaparvata lugens and Laodelphax striatellus. Of the series of compounds tested, 1-isobutyl-and 1-neopentyl-5-(3-trifluoroethoxyphenyl) imidazoles showed the highest activity. 1-Substituted imidazoles terminated the diapause in the pharate first-instar larvae of the silkmoth, Antheraea yamamai. 1-[5-(4-Ethylphenoxy) pentyl] imidazole showed activity comparable to that of KK-42, the most effective compound so far. The injection of KK-42 into fifth instar larvae of the silkworm (Daizo strain), which had been destined to produce diapause eggs, induced the moths to lay non-diapause eggs. Less