Acid-Catalyzed Rearrangements of Nopinic Acid

Herz, Werner; Wahlborg, Harold J.

doi:10.1021/jo01050a503

Cited by 6 publications

(1 citation statement)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The precursor compounds, 1-methyl-4-isopropenyl-2,6-cyclohexadiene (11), 1-methyl-2-acetoxy-4-isopropenyl-2,6-cyclohexadiene (12), 4-isopropyl-1,3-cyclohexadiene-carboxylic acid (13), 4-isopropyl-1,3-cyclohexadiene-1-methanol (14), and 4-isopropyl-1,3-cyclohexadienecarboxylic acid methyl ester (15) were prepared following published procedures. [8][9][10][11] 2. General synthetic procedure for ascaridole (1) and its derivatives (2-10) To each precursor compound such as a-terpine and etc.…”

mentioning

confidence: 99%

Synthesis and nematocidal activity of ascaridole derivatives against Meloidogyne incognita and Aphelenchoides besseyi

2007

View full text Add to dashboard Cite

A series of ascaridole derivatives 1-10 were successfully synthesized and their structures were characterized by 1 H, 13C NMR and high-resolution mass spectroscopy. The nematocidal activities of these compounds were evaluated and the results indicated that these derivatives have better nematocidal activities against Meloidogyne incognita than Aphelenchoides besseyi. Interestingly, cis-isomers of Z-3,6-epidioxy-1-methyl-4-isopropylcyclohexene (2) and Z-3,6-epidioxy-1-methyl-4-isopropenylcyclohexene (4) are more active than their corresponding trans-isomers. Among them, 1,4-epidioxy-4-isopropyl-2-cyclohexenoic acid (8) and 1,4-epidioxy-4-isopropyl-2-cyclohexenecarboxylic acid methyl ester (10) exhibited significant higher nematocidal activities than those of other analogs; therefore the carboxylic acid or carboxyl ester substituent on the ring might be essential for high nematocidal activity. Compared with the toxicity of a commercial nematocide, Oxamyl, these derivatives can be considered effective and promising.

show abstract

mentioning

confidence: 99%