Abstract

A series of ferrocenyl chalcones using acetylferrocene, with ferrocenyl group at the keto carbonyl group, and different aldehydes were synthesized and their bioefficacy evaluation was done against Sclerotium rolfsii, Alternaria solani and Meloidogyne incognita. In continuation of our quest for potent crop protection products, in the present study, a series of 18 substituted ferrocenyl chalcones were synthesized in which ferrocenyl group was attached to the aldehyde moiety, using ferrocenecarboxyaldehyde and different acetophenones by microwave method (MM) and conventional method (CM) [cf: MM 1 to 5 min; CM 12–40 h] and characterized by various techniques viz. IR, LC-HRMS, ¹H-NMR and ¹³C-NMR. In vitro fungicidal activity showed that compound, (2E)-1-(5-Chloro-2-hydroxyphenyl)-3-ferrocenyl-prop-2-en-1-one (34) (ED₅₀ = 21.50 mg L⁻¹) was found to be most active against S. rolfsii and compound, (2E)-1-(4-Bromophenyl)-3-ferrocenyl-prop-2-en-1-one (21) (ED₅₀ = 31.14 mg L⁻¹) showed highest activity against A. solani. As regards nematicidal activity, compound (2E)-1-(3-Bromophenyl)-3-ferrocenyl-prop-2-en-1-one (29) was more potent with LC₅₀ values of 11.95, 8.07 and 4.34 mg L⁻¹ at 24, 48 and 72 h, respectively. QSAR study revealed that MLR for S. rolfsii (r ² = 0.9834, q ²= 0.8975) and A. solani (r ² = 0.9807, q ²= 0.8713) and PLS for M. incognita (r ² = 0.9023, q ²= 0.7818) were the best models.

摘要

合成了一系列使用乙酰基二茂铁的二茂铁基查耳酮，其中二茂铁基在酮基羰基上，并合成了不同的醛类，并对罗勒菌，链格孢菌和根结线虫的生物功效进行了评估。为了继续寻求有效的农作物保护产品，在本研究中，通过微波法（MM）和常规方法，使用二茂铁羧醛和不同的苯乙酮，合成了18个取代的二茂铁基查耳酮，其中二茂铁基与醛部分相连。 （CM）[比照：MM 1至5分钟；CM 12–40 h]，并通过各种技术来表征。红外，LC-HRMS，¹ H-NMR和¹³核磁共振。体外杀真菌活性表明，化合物（2 E）-1-（5-氯-2-羟基苯基）-3-二茂铁基-丙-2-烯-1-酮（34）（ED ₅₀ = 21.50 mg L ^-1）被发现对S. rolfsii和化合物（2 E）-1-（4-溴苯基）-3-二茂铁基-丙-2-烯-1-酮（21）（ED ₅₀ = 31.14 mg L ^-1）表现出最高的抗农杆菌。关于杀线虫活性，化合物（2 E）-1-（3-溴苯基）-3-二茂铁基-丙-2-烯-1-酮（29）在LC ₅₀下更有效分别在24、48和72小时时的11.95、8.07和4.34 mg L ^-1值。QSAR研究表明，对于MLR白绢病菌（- [R ² = 0.9834，q ² = 0.8975）和A.菌（- [R ² = 0.9807，q ² = 0.8713）和PLS为南方根结线虫（- [R ² = 0.9023，q ² = 0.7818）是最好的模型。