The Preparation and Bacteriostatic Activity of Halogenated Carbanilates

Beaver, D. J.; Roman, Daniel P.; Stoffel, P. J.

doi:10.1021/jm00341a006

Cited by 11 publications

(4 citation statements)

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“…°Substituted phenyl carbanilates were recrystallized from dioxane and phenyl and alkyl carbanilates from hexanechloroform.6 Cottin and Mocotte (1964) = Beaver et al (1963)…”

mentioning

confidence: 99%

Structure-reactivity relationships in the hydrolytic degradation of propham, chlorpropham, swep, and related carbamates

Bergon¹,

Calmon²

1983

J. Agric. Food Chem.

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The alkaline hydrolysis of propham, chlorpropham, and swep to carbanilic acids was investigated for sodium hydroxide concentrations ranging from 0.01 to 4.0 N. The dependence of the observed pseudo-first-order rate constants on the hydroxide ion concentration was in agreement with the rate laws of the two reaction mechanisms-ElcB and Bh2-that can be involved in the hydrolysis of carbamates. The values of the ionization constants of propham (pKa = 15.0), chlorpropham (pKa = 14.45), and swep (pKa = 13.9) account for their behavior in aqueous media. The Hammett p value of 0.98 obtained for the hydrolysis of a series of isopropyl carbanilates, the activation entropy of swep and the changeover in reaction mechanism, from ElcB to BA,2, observed in the hydrolysis of alkyl and aryl 3,4-dichlorocarbanilates are decisive arguments supporting the involvement of a B&2 reaction scheme in the hydrolysis of propham, chlorpropham, and swep. The formation of phenyl isocyanate during the degradation of these herbicidal carbanilates can therefore be ruled out.

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“…°Substituted phenyl carbanilates were recrystallized from dioxane and phenyl and alkyl carbanilates from hexanechloroform.6 Cottin and Mocotte (1964) = Beaver et al (1963)…”

mentioning

confidence: 99%

Structure-reactivity relationships in the hydrolytic degradation of propham, chlorpropham, swep, and related carbamates

Bergon¹,

Calmon²

1983

J. Agric. Food Chem.

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“…There has been a growing interest, during the last few years, in the synthesis and biological evaluation of compounds containing the N*-N*-S* or 0*-N*-S* tridentate ligand system (3,(6)(7)(8)(9) or arylazo grouping (10,12). This interest stems mainly from certain interesting antituberculous activities of disubstituted thiocarbamides (1,11). As a part of a general study directed towards the development of antituberculous agents, the above mentioned rationale led to the examination of the synthesis and biological properties of /V-aryl-/V-2-(4-phenyl-5-arylazothiazolyl)thiocarbamides having N*-N*-S* ligand and arylazo grouping and a modified azomethine linkage.…”

Section: Literature Citedmentioning

confidence: 99%

Potential antituberculous agents. 3. N-Aryl-N'-2-(4-phenyl-5-arylazothiazolyl)thiocarbamides

Srivastava¹,

Upadhyaya²,

Sharma³

1976

J. Chem. Eng. Data

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“…0-[(Substituted)carbamoyl]-3hyclroxypropionitriles (Table I). All of these derivatives were prepared in a similar manner using the method of Beaver et al (1963). A mixture consisting of 0.033 m of the appropriate isocyanate and 0.033 m of 3-hydroxvpropionitrile was heated in an oil bath at 80°for 6 hr under anhydrous conditions.…”

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confidence: 99%

Homeosterically related plant growth regulators. I. Synthesis

Skinner¹,

Sargent²

1973

J. Agric. Food Chem.

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At rates of application ranging from 1.5 to 3.0 kg of ai / ha, PH 40-51 proved to be an effective and safe black grass herbicide in autumn-sown wheat. At these dosages, a number of important broad-leaved weeds are also satisfactorily controlled. The apparent effectiveness against wild oats in cereals merits further evaluation. Studies on the synthesis of PH 40-51 have so far not resulted in a process which is economically acceptable. LITERATURE CITED

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The Preparation and Bacteriostatic Activity of Halogenated Carbanilates

Cited by 11 publications

References 0 publications

Structure-reactivity relationships in the hydrolytic degradation of propham, chlorpropham, swep, and related carbamates

Structure-reactivity relationships in the hydrolytic degradation of propham, chlorpropham, swep, and related carbamates

Potential antituberculous agents. 3. N-Aryl-N'-2-(4-phenyl-5-arylazothiazolyl)thiocarbamides

Homeosterically related plant growth regulators. I. Synthesis

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