42404-06-8

Usage

Uses

Propachlor-2-hydroxy is a metabolite or photodegrdation product of propachlor herbicide.

Upstream product

• 1918-16-7 2-chloro-N-(1-methylethyl)-N-phenylacetamide 

Downstream Products

• 139504-62-4 5-(1-methyl-2-chloro-2,3,3-trifluoro-1-cyclobutyl)-1,3,4-thiadiazol-2-yl-oxyacetic acid-N-isopropyl-anilide 

Relevant academic research and scientific papers

Acid- and base-catalyzed hydrolysis of chloroacetamide herbicides

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.

Kinetics and Mechanism of the Nucleophilic Displacement Reactions of Chloroacetanilide Herbicides: Investigation of α-Substituent Effects

The ease with which α-chloroacetanilide herbicides undergo displacement reactions with strong nucleophiles, and their recalcitrance toward weak ones, is intimately related to their herbicidal properties and environmental chemistry. In this study, we investigate the kinetics and mechanisms of nucleophilic substitution reactions of propachlor and alachlor in aqueous solution. The role played by the α-amide group was examined by including several structurally related analogs of propachlor possessing modified α substituents. The overall second-order nature of the reaction, the negative ΔS? values, the weak influence of ionic strength on reactivity, and structure-reactivity trends together support an intermolecular SN2 mechanism rather than an intramolecular reaction for α-chlomacetanilides as well as the a-chlorothioacetanilide analog of propachlor. In contrast, the α-methylene analog exhibits kinetics and a salt effect consistent with anchimeric assistance by the aniline nitrogen. Electronic interactions with the α-anilide substituent, rather than neighboring group participation, can be inferred to govern the reactivity of α-chloroacetanilides toward nucleophiles.

Herbicidal N-isopropylheteroaryloxyacetanilides

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

Phenyl alpha-acyloxyacetamide derivatives and their therapeutic use

Therapeutic as well as preventive measures to alleviate the symptoms of dermatologic and other conditions and disorders with phenyl alpha-acyloxyacetamide derivatives is disclosed. Dermatologic and other conditions and disorders in humans in which the compounds may be useful include pruritus, atopic dermatitis, eczema, psoriasis, acne, dry skin, dandruff, malodors of integumental areas; and various aches, pains and discomforts of skin, joints and other body parts. The phenyl alpha-acyloxyacetamide derivatives include, for example, N-ethyl phenyl alpha-acetoxyacetamide, N-benzyl phenyl-alpha-acetoxyacetamide, N-phenethyl phenyl-alpha-acetoxyacetamide, N-benzyl diphenyl-alpha-acetoxyacetamide and N-phenethyl diphenyl-alpha-acetoxyacetamide. The compositions containing the active ingredients are also useful for treatment of skin conditions or disorders, and musculoskeletal disorders, of domestic animals, for example dogs, such as dry skin, scurf, eczema, mange, prurigo, malodors, arthritis or myositis. Some phenyl-alpha-acyloxyacetamide derivatives may have a tranquilizing effect.

Substituted o-[aminosulfonyl]-glycolic anilides

New and valuable substituted O-[aminosulfonyl]-glycolic anilides and a process for controlling the growth of unwanted plants with these compounds.