A Convenient Synthesis of N', N'-Disubstituted N-Fluorophenylformamidines by Using Microwave and Their Insecticidal Activities

Phenylformamidine derivatives are well known as insecticides for their specific activity against the insects. It has now been established that they show insecticidal activity as agonists on the octopamine receptor which is located in the synapse membrane. The reaction of triethylorthoformate and fluoroanilines gave formimidates (1) in good yields and N',N'-Disubstituted N-fluorophenylformamidine derivatives were synthesized more easily by using microwave. This microwave reaction condition gave products in high yields and faster reaction time than conventional methods. All the compounds were screened for their biological activity agaist harmful insects of plant hoppers, moths, aphids and mites. Synthetic compounds of 2-I-a, 2-I-c, 2-I-d, 2-II-d showed good activity against mites and plant hoppers.

마이크로웨이브를 이용한 N', N'-Disubstituted N-Fluorophenylformamidine 유도체의 편리한 합성과 살충활성

Phenylformamidine계 유도체들은 곤충의 신경전달 물질인 octopamine과 경쟁적으로 octopamine receptor에 작용하여 살충 활성을 나타낸다. 불소를 함유한 4-fluoro-2-methylaniline과 2-fluoro-4-methylaniline을 트리에틸오르토포메이트와 반응시켜 얻은 중간체 formimidate(1)을 마이크로웨이브 조건하에서 반응시켜 짧은 반응시간 내에서 높은 수율로 새로운 화합물인 다양한 N', N'-fluorophenylformamidine 유도체들을 합성하였으며 이들 화합물의 복숭아 흑진딧물, 배추좀나방, 점박이응애, 그리고 벼멸구 등에 대한 살충활성을 시험하였다. 2-I-a, 2-I-c, 2-I-d, 2-II-d 화합물들이 응에류와 멸구유에 좋은 살충활성을 보여주었다.