Fungicidal Activities of α-Methoxyphenylacetic Acid Derivatives

Abstract

A number of a-alkoxyphenylacetic acid derivatives were synthesized and their fungicidal activities were examined. Studies of structure-activity relationships revealed strong fungicidal activity when the substituent at the a-position was a methoxy group and a substituted phenoxymethyl group was introduced to the 2-position of the benzene ring of the phenylacetic acid moiety. When a substituted phenoxy group was introduced to this position, the fungicidal activity was very weak. It was also shown that N-methylphenylacetamide derivatives had stronger activities than phenylacetic acid methyl ester derivatives. Among the compounds synthesized in this study, 2-[2-(2, 5-dimethylphenoxymethyl)phenyl] -2-methyl-Nmethylacetamide (35) showed the most potent fungicidal activity against a wide range of crop diseases.

2-Chloro-2,2-difluoroacetophenone: A Non-ODS-Based Difluorocarbene Precursor and Its Use in the Difluoromethylation of Phenol Derivatives

“…Difluoromethoxy (OCF 2 H) functionality plays an important role in many bioactive organic molecules and in liquid crystal materials for display applications . Although aliphatic difluoromethoxy-containing compounds have important applications such as anesthetics, recently, more attention has been paid to the compounds bearing an aromatic difluoromethoxy group, i.e., aryl difluoromethyl ethers. − Many aryl difluoromethyl ethers have found applications such as enzyme inhibitors, anti-HIV agents, antimicrobial agents, potassium channel activators, fungicides, pestcides, herbcides, and smectic phase liquid crystals …”

“…1 Although aliphatic difluoromethoxy-containing compounds have important applications such as anesthetics, recently, more attention has been paid to the compounds bearing an aromatic difluoromethoxy group, i.e., aryl difluoromethyl ethers. [1][2][3][4][5][6][7][8][9] Many aryl difluoromethyl ethers have found applications such as enzyme inhibitors, 2 anti-HIV agents, 3 antimicrobial agents, 4 potassium channel activators, 5 fungicides, 6 pestcides, 7 herbcides, 8 and smectic phase liquid crystals. 9 Despite the fact that numerous structurally diverse aryl difluoromethyl ethers were synthesized during the past half century, efficient synthetic methods are few.…”

Cytotoxic Evaluation and Determination of Organic and Inorganic Eluates from Restorative Materials

“…In this material, MOPA was found to be the dominant compound among the substances eluted, and its concentration was significantly higher at one month observation period in methanolic solutions. MOPA was eluted only from Activa Bioactive Restorative and, along with its derivatives, has fungicidal activity against specific fungal strains [ 51 , 52 ]. Additionally, during the analysis, this material presented a complex initiation system, which could possibly relate to the three chemical reactions taking place during the setting process.…”

Organic Eluates Derived from Intermediate Restorative Dental Materials

“…MOPA was found to be the dominant compound among the other eluted components of the ACTIVA TM extract. Previous studies have proven the fungicidal activities of MOPA [39] and its corresponding derivatives [40] against specific fungal strains. Acetophenone (ACP), and mostly its derivatives like 2,2-dimethoxy-2-phenyl acetophenone (DMPA), are widely spread as type I photoinitiators yielding free-radicals due to a unimolecular bond cleavage [41][42][43][44][45].…”