Investigations on fungicides

Abstract

SUMMARY The structure/anti‐fungal relationships of a group of 137 sulphur‐containing compounds were studied by observation of their effects on the mycelial growth of six fungi, Pythium ultimum, Sclerotinia fructigena, Verticillium albo‐atrum, Alternaria solani, Botrytis cinerea and Aspergillus niger, and the germination of spores of Botrytis cinevea. These compounds consist of (a) salts and (b) carboxy‐alkyl and ‐alkenyl esters of both alkyl‐ and aryl‐substituted dithiocarbamic and hydroxydithioformic acids, (c) certain cyclic derivatives of (b), and (d) alkyl and aryl isothiocyanates. Short homologous series were selected to assess the importance of physico‐chemical properties in fungitoxicity, whilst certain aryl‐substituents were used on the basis of their contrasting electronic effects. Derivatives of alkoxydithioformic acids showed higher toxicity than those of N‐alkyl‐substituted dithiocarbamic acids, except for a series of β‐(N‐alkylthio‐carbamoylthio)acrylic acids. The fungitoxicity of esters of alkyl‐substituted dithiocarbamic or hydroxydithioformic acids showed little change on increasing the size of the alkyl substituent or ester grouping. The fungitoxicity of compounds derived from N‐aryldithiocarbamic acids varied considerably with the nature of the N‐substituent.

2-{[Bis(propan-2-yl)carbamothioyl]sulfanyl}acetic acid

“…Compound 1 was prepared in good yield (60%) from a two-step reaction, that is, the in situ reaction of N,N-diisopropylamine, carbon disulfide, and sodium hydroxide to generate the dithiocarbamate, which was then reacted with sodium chloroacetate; this procedure follows several literature precedents [1,[5][6][7][8]. The final product was characterized by spectroscopy ( 1 H and 13 C{ 1 H} NMR, IR, and UV); see Supplementary Materials for original spectra.…”

“…Recent [1,2] interest in organotin compounds containing this dithiocarbamate ester of a carboxylic acid arises from the known cytotoxicity or potential anticancer activity of organotin carboxylates [3] and organotin dithiocarbamates [4]. Compound 1 has been known for over 50 years being first described in 1963 [5][6][7][8]. Original interest in this compound and related species revolved around potential fungicidal activity [5], antibacterial investigations [6], and herbicidal activity [8].…”

“…Compound 1 has been known for over 50 years being first described in 1963 [5][6][7][8]. Original interest in this compound and related species revolved around potential fungicidal activity [5], antibacterial investigations [6], and herbicidal activity [8]. Despite these investigations, detailed spectroscopic characterization of 1 and studies to determine its crystal structure are lacking.…”

Structure-activity relations in antifungal agents. A survey

“…For this reason we have used log P values for the ion pair, RCOONa, in correlating these compounds instead of log P for the neutral RCOOH. Equation 35 will not be considered with the others since this work was done at pH 5.6 rather than the pH 6.5 employed in the other work. Two equations (6 and 7) are for killing action and have, as expected, a lower mean intercept of 2.3 while five equations (8, [48][49][50][51] are for inhibitory action and have a mean intercept of 3.5±0.7.…”

Triton-B Catalyzed One Pot Multicomponent Synthesis of Isothiocyanates in Non-Aqueous Medium

“…Isothiocyanates are a group of vital class of compounds utilized in natural products, synthetic and medicinal fields as antimicrobial [1,2], antitumor [3][4][5][6], antiproliferatives [7], enzyme inhibitors for the HIV virus [8,9] and other biological assays of DNA and protein [10][11][12]. Isothiocyanates are also used as effective synthetic intermediates in nucleophilic addition and cycloaddition reactions.…”