42404-06-8Relevant articles and documents
Acid- and base-catalyzed hydrolysis of chloroacetamide herbicides
Carlson, Daniel L.,Than, Khoi D.,Roberts, A. Lynn
, p. 4740 - 4750 (2006)
Despite the prevalence of chloroacetamides as herbicides, little is known about the rates or products of acid- or base-catalyzed hydrolysis of these compounds. Mechanisms of acid-catalyzed reactions may parallel those catalyzed by (hydr)oxide minerals, while base-catalyzed processes have as important counterparts reactions with environmental nucleophiles (such as reduced sulfur species). The current study systematically investigates how the structure of nine chloroacetamides affects their reactivity in 2 N NaOH, 2 N HCl, or 6 N HCl at 25 or 85°C. Base-catalyzed hydrolysis proceeds either through an intermolecular SN2 reaction to hydroxy-substituted derivatives or (in a few cases) through amide cleavage, while both amide and ether group cleavages are observed under acidic conditions. Our results reveal that subtle differences in chloroacetamide structure [notably the type of (alkoxy)alkyl substituent] can dramatically influence reactivity and reaction mechanism. Hydroxy-substituted, morpholinone, and secondary aniline derivatives were identified upon reaction for several years in deionized water at circumneutral pH.
Herbicidal N-isopropylheteroaryloxyacetanilides
-
, (2008/06/13)
Herbicidal N-isopropylheteroaryloxyacetanilides of the formula STR1 in which A stands for nitrogen or the group C--R3 where R3 stands for halogen, cyano, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, alk
Substituted o-[aminosulfonyl]-glycolic anilides
-
, (2008/06/13)
New and valuable substituted O-[aminosulfonyl]-glycolic anilides and a process for controlling the growth of unwanted plants with these compounds.