细交链孢菌酮酸（Tenuazonic acid，简称TA）即 3-乙酰基-4-羟基-5-仲丁基吡咯啉-2-酮，为链格孢菌(Alternaria)的代谢产物，是一种天然毒素。因其具有一定的药物活性，对革兰阳氏细菌和白血病细胞肿瘤有抑制作用，而一直用于抗细菌、真菌、肿瘤药物的研究。后来，人们还发现细交链孢菌酮酸对杂草具有明显的除草活性，几乎对所有常见杂草都有效。细交链孢菌酮酸是生物源天然代谢物，在进入土壤后，很快钝化并失去活性，因而具有相当高的环境安全性。近年来，具有植物生长调节活性、除草活性和抑菌活性的氨基酸酯Schiff碱类化合物的研究越来越受到关注。为了筛选具有更好生物活性、低毒、易降解的新化合物，同时为研究TA衍生物结构与生物活性的关系提供更多信息，我们设计并合成了一系列具有氨基酸酯Schiff碱结构的吡咯啉-2-酮类化合物，并进行了除草活性和杀菌活性测定。 以天然氨基酸为原料，通过与氯化亚砜和醇反应生成氨基酸酯盐酸盐，同时以取代苯胺为原料，与氯乙酸乙酯反应合成N-取代甘氨酸乙酯。然后分别用氨基酸酯盐酸盐和N-取代甘氨酸乙酯与双乙烯酮、甲醇钠反应，得到5个细交链孢菌酮酸及其类似物，然后分别与8种不同的氨基酸酯盐酸盐反应得到22个结构新颖的3-(1′-烃氧甲酰基甲基亚胺基)乙基-4-羟基吡咯啉-2-酮类衍生物，并用元素分析、质谱、红外光谱和氢核磁共振谱对目标化合物进行了结构表征。 随后采用油菜平皿法和稗草平皿法测定了目标化合物的除草活性。结果表明，在100mg/L浓度下，化合物4b、4g、4h、4j和4o对油菜根长的抑制率达到了80%以上，化合物4g和4h对稗草芽长的抑制率也达到了80%以上。同时采用菌丝生长抑制法测定了目标化合物对3种植物病原菌（小麦纹枯菌、小麦赤霉菌和黄瓜炭疽菌）的抑菌率。结果表明，在100mg/L浓度下，化合物4b、4g、4h、4j、4m和4o对黄瓜炭疽菌具有较好的抑制作用，抑制率达到60%以上，抑菌效果明显高于TA。

Tenuazonic acid (TA, 3-Acetyl-4-hydroxy-5-sec-butylpyrroline-2-one) was an important mycotoxin from Alternaria alternate. Originally, it was found that TA exhibited good medical activities against gram-positive bacteria and leukemia tumor cells and was used to research new antibacterial, antifungal and antineoplastic drugs. In recent years, people also founded that TA presented obvious and extensive herbicidal activities. As a kind of natural product, TA can be degraded rapidly by the soil microorganisms, and is friendly with the environment. During these years, more and more compounds possessing the structures of amino acid ester and Schiff base, which displayed the activities of plant growth regulator, herbicide and fungicide were synthesized. In order to find novel, degradable and low-toxic compounds with better biological activities, and provide more valuable information concerning the structure-activity relationships of TA derivatives. Twenty-two compounds possessing the structures of pyrroline-2-one, amino acid ester and Schiff base were designed and synthesized, and their herbicidal and fungicidal activities were also evaluated. Amino acid ester hydrochlorides were synthesized with natural amino acids and thionyl chloride, and N-arylglycine ethyl esters were prepared with anilines and ethyl chloroacetate. The N-arylglycine ethyl esters and amino acid ester hydrochlorides were reacted with diketen, MeONa, respectively, to give 5 intermediates 3-acetyl-4-hydroxypyrroline-2-one derivatives. Then, these intermediates were reacted with 8 different amino acid ester hydrochlorides to obtain 22 novel 3-(1′-alkyloxycarbonylmethylimino)ethyl-4-hydroxylpyrroline-2-one derivatives. Structures of the target compounds were confirmed by 1H NMR, MS, IR spectra and elemental analysis. The herbicidal activities of the target compounds were evaluated by the petri dish test method with Brassica napus (as a sample of annual dicotyledonous plant) and Echinochloa crusgalli (as a sample of annual monocotyledonous plant). The tested results indicated that the compounds 4b, 4g, 4h, 4j and 4o against Brassica napus, and 4g, 4h against Echinochloa crusgalli all exhibited over 80% of inhibition rates at the concentration of 100 mg/L. The antifungal activities of the target compounds were tested by the mycelial growth petri dish test method against 3 kinds of plant fungi Rhizoctonia cerealis, Colletotrichum orbiculare and Fusarium graminearum. The results indicated that the compounds 4b, 4g, 4h, 4j, 4m and 4o showed selective inhibition rates over 60% against Colletotrichum orbiculare at the concentration of 100 mg/L, the antifungal activities is obviously better than that of TA.