Metabolism of a Pyrrolidine Urea Herbicide in Corn and Weeds

Holm, Robert E.; Stallard, Don E.

doi:10.1017/s0043174500036419

Cited by 10 publications

(4 citation statements)

References 11 publications

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“…cis-2,5-Dimethyl-l-pyrrolidinecarboxanilides have been shown to inhibit photochemical activity (Hill reaction) of isolated spinach chloroplasts (Holm and Stallard, 1974). trans-2,5-Dimethyl-l-pyrrolidinecarboxanilides were completely inactive.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and herbicidal activity of pyrrolidinecarboxanilides

Pyne¹,

Szabo²,

Holm³

1974

J. Agric. Food Chem.

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A series of pyrrolidinecarboxanilides and pyrrolidinethiocarboxanilides has been prepared and found to be herbicidally active. Substitution of methyl groups in the cis configuration at the 2 and 5 positions of the pyrrolidine ring of the carboxanilides increased the herbicidal activity, while methyl groups in the trans configuration reduced or eliminated the activity. In general, the thiocarboxanilides were less active than the corresponding carboxanilides. Pyrrolidinecarboxanilides were very active inhibitors of the Hill reaction and the degree of inhibition correlated with the accumulation of nitrite in tissue. cis-2,5-Dimethyl-l-pyrrolidinecarboxanilide, one of the most herbicidally active compounds in the series, has undergone extensive field testing and is being developed as a selective corn herbicide.Synthesis and biological evaluation of a series of pyrrolidine and alkylpyrrolidinecarboxanilides were initiated after several were found to have pre-and postemergence herbicidal activity. Synthesized compounds were evaluated in standard greenhouse herbicide tests and in special tests using isolated chloroplasts and excised leaf sections. From this work one compound, cis-2,5-dimethyl-l-pyrrolidinecarboxanilide ( l ) , has been selected for further development and commercialization.@ YH-C-9 N c FJ CH, 1 Compound 1, known by the trade name Rowtate, has been field tested for 2 years as a selective corn herbicide. In these tests, Rowtate has controlled broadleaf and certain grassy weeds in corn at 2-3 kgfha, depending on soil type. MATERIALS AND METHODSPhenyl isocyanates and thioisocyanates were purchased from commercial sources or were prepared by the reaction of phosgene and the appropriate aniline in ethyl acetate.

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Section: Resultsmentioning

confidence: 99%

“…The Hill reaction assay was performed using chloroplasts isolated from spinach leaves according to the procedure published previously (Holm and Stallard, 1974).…”

Section: Methodsmentioning

confidence: 99%

Synthesis and herbicidal activity of pyrrolidinecarboxanilides

Pyne¹,

Szabo²,

Holm³

1974

J. Agric. Food Chem.

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“…Part of the corn seed was treated with 0 5'/o Protect. Corn plants were harvested at various times after planting and extracted using a procedure which removed 95" " of the radioactivity from the tissue and separated 5328 from its water soluble metabolites (Holm & Stallard, 1974).…”

Section: Resultsmentioning

confidence: 99%

“…The soil was washed from the roots which were separated from the shoots for subsequent extraction. The extraction procedure for the purification and indentification of 5328 and its water soluble metabolites was described previously (Holm & Stallard, 1974).…”

Section: Methodsmentioning

confidence: 99%

Increased metabolism of a pyrrolidine urea herbicide in corn by a herbicide antidote

Holm

Szabo

1974

Weed Research

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Corn, cotton, and sorghum plants were injured by high rates of 5328 (rM-2.5-dimeihyI-l-pyiToIidinccarboxanilide) when it was applied lo the soil surface al planting time. Tlic injury was severe al 35-84 kg^ha {eight times recommended dosage) and in com resulted in complete inhihiiion of adventitious root development and reduced shoot and primary and secondary root growth. Treatment of the seeds with 0 5''o Protect (1,8-naphthaIic anhydride) prior to planting dramatically decreased the injurious effect of 5328 on corn, sorghum, and cotton. Using '*C-5328 in corn, it was shown that Prolccl did not allcr herbicide uptake. However, the rate of conversion of the herbicide molecule in corn tissue lo water soluble, nonhcrbicidal metabolites was markedly enhanced in plants grown from Proteci-treated seeds. Accroissement du metabolisme d'une pyrrolidine ur^e herbicide dans le mats par un aniidoieDes plantes de mats, de eoton, de sorgho, ont iti endommagccs par des doses fortes de 5328 (cis-2,S-d']mtihyl-]• pyrroiidine-curboxanitide) quand ce produit a Hi applique k la surface du sol au moment du semis. Lcs degats ont ^te imporiants & 35,84 kg/ha (huit fois la dose recommandSe) el il en est r6sult6 pour le mats une inhibition complete du d6veloppement des racines adveniives et une reduction de la croissance de la lige et des racines primaires et secondaircs. Le Iraitement des semences avec du 'Protect' ^ 0,5 "" (anhydride 1,8-naphlalique) avant le semis a r^duit d'une fa^on inattendue les effects toxiques du 5328 sur le mais, le sorgho et le coton. L'utilisation du '''C-5328 dans le mals ^ permis dc montrer que le "Protect' ne modifie pas l'absorption de rherbicidc. Cependant le laux de conversion dans le lissu de mals, de la molecule herbicide en metabolites non herbicides et hydrosolubles a 6t^ accru de fa^on marqu^ dans les plantes issues de semences trait^cs avec le "Protect". Gesteigerrer Metabolismus elites PyrroIidliAarnstoffherbizids in Mais durch ein Herbizidantidote Mais. Baumwolte und Hirse wurden durch hohe Aufwandmcngcn von 5328 (cis-2.5-Dimcthyl-l-pyrrolidincarboxanilid) geschSdigt, wenn das Herbizid zur Saat auf den Bodert ausgebrachl wurde. Die Schadigung war bei 35,84 kg.'ha (das Achlfache der empfohlenen Aufwandmenge) sehr stark. Dabei wurde bei Mais die Entwicklung der Adventivwurzein vijilig gehemmi und das Sprosswachstum, sowie das Wachstum der Primar-und SekundSrwurzeln vermindert. Die Behandlung des Saatguts mit 0,5°; Proiect (Naphlhulsaurcanhydrid) vor der Saat vermindcrte die schadigende Wirkung von 5328 bei Mais. Hirse und Baumwollc enischeidcnd. Uniersuchungen mit '•*C-5328 und Mais zeigten. dass Protect die Herbi/idaulnahme nicht bceinflusste. Die Umwandlung des Herbi/idmolektlls im Maisgewebe in wasserlOsliche, nicht-berbizide Meiaboliten war in Plianzcn aus Proteclbehandeliem Saatgut deutlich gesteigerl.

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A new synthesis of 2,5‐dimethyl‐1‐pyrroline

METZ¹,

Scozzie²

1975

Journal of Heterocyclic Chem

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Metabolism of a Pyrrolidine Urea Herbicide in Corn and Weeds

Cited by 10 publications

References 11 publications

Synthesis and herbicidal activity of pyrrolidinecarboxanilides

Synthesis and herbicidal activity of pyrrolidinecarboxanilides

Increased metabolism of a pyrrolidine urea herbicide in corn by a herbicide antidote

A new synthesis of 2,5‐dimethyl‐1‐pyrroline

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