신농약 개발을 목적으로 isosterism 이론을 근거로 하여 선도화합물인 2-imino-1,3-thiazoline 의 분자 수정을 통하여 분자내에 1,3-thiazoline과 urea기가 포함된 새로운 화합물 4를 디자인하였다. N-Alkylthiourea 5와 bromoacetonitrile을 에탄올 용액 중에서 반응시켜 위치 선택적으로 생성된 2,4-diimino-1,3-thiazolidine 브롬산 염 6을 isocyanate 유도체와 반응하여 화합물 4의 tautomer인 화합물 8을 얻었다. 합성된 화합물 13종을 대표적인 6종의 식물병원균, 벼 도열병, 벼 잎집무늬마름병, 오이 잿빛곰팡이병, 토마토 역병, 밀 붉은녹병, 보리 흰가루병 등에 대한 in vivo 항균력 시험을 하였다. 합성된 화합물 8의 벼 도열병원균에 대한 항균력은 2-phenylimino-1,3-thiazoline 1과 비교할 때 매우 낮았으며, 일부 화합물에서 밀붉은녹병에 대한 미약한 항균력을 나타냈다.
For the purpose of a development of new agrochemical fungicides, new compound 4 in which 1,3-thiazoline scaffold as well as urea moiety in the structure was designed through molecular modification of lead compound, 2-imino-1,3-thiazone based on isosterism. The reaction of N-alkylthiourea 5 and bromoacetonitrile in ethanol gave 2,4-diimino-1,3-thiazolidine hydrobromide 6 regioselectively, which was treated with isocyanates gave the corresponding 8 which is tautomer of 4. Antifungal screening (in vivo) of the synthesized compound 8 against typical plant diseases, which include rice blast, rice sheath blight, cucumber gray mold, tomato late blight, wheat leaf rust, and barley powdery mildew, was carried out. Antifungal activities against rice blast of the compound 8 were weaker than those of 2-phenylimino-1,3-thiazoline 1. Some compounds showed weak antifungal activities against wheat leaf rust.
