Herbicidal Activity, Molecular Size vs. Herbicidal Activity of Anilides

Huffman, C. W.; Allen, S. E.

doi:10.1021/jf60110a012

Cited by 17 publications

(4 citation statements)

References 3 publications

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“…The herbicida! activity of 3,4dichloroanilides was investigated by Huffman and Allen (1960). They observed that the 7V-acetyl and formyl derivatives were phytotoxic, but were not as effective as propanil.…”

Section: Methodsmentioning

confidence: 99%

“…Replacement of the ethoxy group takes place readily; however, we found that the analogous acetyl compound could not be obtained by this method and much more vigorous conditions are required (Fieser and Fieser, 1967). The herbicidal activity of 3,4-dichloroanilides was investigated by Huffman and Allen (1960). They observed that the N-acetyl and formyl derivatives were phytotoxic, but were not as effective as propanil.…”

Section: (No Halogen)mentioning

confidence: 99%

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Metabolism of 3,4-dichloroaniline in soils

Kearney¹,

Plimmer²

1972

J. Agric. Food Chem.

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Section: Methodsmentioning

confidence: 99%

Section: (No Halogen)mentioning

confidence: 99%

Metabolism of 3,4-dichloroaniline in soils

Kearney¹,

Plimmer²

1972

J. Agric. Food Chem.

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“…The chlorinated anilines, azobenzene derivatives and metabolites such as nitro-, nitroso-, and hydroxylamino aromatics, phenoxazines etc., are found to be phytotoxic, 115 mutagenic, carcinogenic, 4 -36 ' 113 -114 toxic to mammalian cells, 3 ' 116 and have an antimicrobial activity. 29 ' 117 Some are responsible for methemoglobin in biological systems and anemia.…”

Section: Toxicity Of Reaction Products and Metabolitesmentioning

confidence: 99%

Fate of anilines and related compounds in the environment. A review

Adrian

Andreux²,

Viswanathan

et al. 1989

Toxicological & Environmental Chemistry

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The environmental aspects of the fate of anilines and related compounds are examined. They include the ecotoxicological aspects, the physico-chemical and (bio)chemical reactions in the gas phase, aquatic environments, plants and soil. The particularity of this class of substances is the formation of "bound residues" in high quantities, up to 95% in soil within one vegetation period. Some new results on the catalytically induced incorporation of anilines in soil organic matter are presented.

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“…); and IPC (isopropyl-Nphenylcarbamate) was a gift from Pittsburgh Plate Glass Co. (Pittsburgh, Pa.). Acetanilide, 4-nitroacetanilide, a-chloroacetanilide, and formanilide were purchased (Aldrich Chemical Co., Inc., Milwaukee, Wis.), and propionanilide, butyranilide, p-acetaniside, and 4-chloroacetanilide were synthesized by the acylation of their corresponding arylamines by the appropriate acid chloride as described by Huffman and Allen (7). The products were recrystallized from suitable solvents until all detectable arylamine had been removed.…”

Section: Methodsmentioning

confidence: 99%

Herbicide Transformation

Lanzilotta¹,

Pramer²

1970

Applied Microbiology

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Replacement cultures liberated 3,4-dichloroaniline (DCA) from 3,4-dichloropropionanilide (propanil). The kinetics of the conversion suggest a requirement for de novo enzyme synthesis, but the system was not influenced by chloramphenicol or puromycin. Enzyme activity was detected when acetanilide (Km = 0.195 mM) was used to replace propanil as substrate. Fungal acylamidase (E.C. 3.5.1., an aryl acylamine amidohydrolase) was concentrated by salt precipitation and characterized. The Fusarium solani acylamidase exhibited an optimum at pH 7.5 to 9.0 and was inactivated in 10 min at 50 C. The enzyme was not sensitive to methyl-carbamate or organophosphate insecticides, but the herbicide, Ramrod (N-isopropyl-2-chloroacetanilide), acted as a competitive inhibitor of acetanilide hydrolysis (Ki = 0.167 mM). Hydrolysis rates were decreased by various para substitutions of acetanilide. Chloro substitution in the acyl moiety of acetanilide also reduced the rate of hydrolysis. 3,4-Dichloroacetanilide was less susceptible to enzyme action than acetanilide, but 3,4-dichloropropionanilide was hydrolyzed much more rapidly than propionanilide. The fungal acylamidase was highly specific for N-acetylarylamines. It did not catalyze hydrolysis of formanilide, butyranilide, dicryl, Karsil, fenuron, monuron, or isopropyl-N-phenylcarbamate. It appears to differ from acylamidases that have been isolated from rice, rat liver, chick kidney, and Neurospora.

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Herbicidal Activity, Molecular Size vs. Herbicidal Activity of Anilides

Cited by 17 publications

References 3 publications

Metabolism of 3,4-dichloroaniline in soils

Metabolism of 3,4-dichloroaniline in soils

Fate of anilines and related compounds in the environment. A review

Herbicide Transformation

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