Metabolism of Herbicides, Metabolism and Translocation of 3-Amino-1,2,4-triazole by Canada Thistle

Herrett, Richard A.; Bagley, William P.

doi:10.1021/jf60131a006

Cited by 20 publications

(14 citation statements)

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“…From this it may be hypothesized that aminotriazole itself does not possess phytocidal properties but has to be metabolized into X3 before any phytocidal effect can occur. The phytocidal and physiological properties of X3 are very similar to those of Unknown III, a metabolite reported by Herrett & Bagley (1964), but X3 and Unknown HI differ in chromatographie behaviour and are unlikely to be identical. The metabolite X3 showed a tendency to hydrolyse back to aminotriazole in vitro, but this process appeared quite slow.…”

Section: Metabolism Of Aminotriazole In Oatssupporting

confidence: 51%

“…Hereafter in this paper, the two main metabolites will be designated Unknown I and Unknown II. The two main aminotriazole metabolites discussed are both considered to be detoxication products (Herrett & Linck, 1961;Herrett & Bagley, 1964). Volger (1969) also reported phytocidally inactive aminotriazole metabolites from bracken [Pteridium aquilinum (L.) Kuhn).…”

Section: Introductionmentioning

confidence: 99%

“…Aminotriazole is reported to be readily mobile in both symplast and apoplast (Crafts, 1964;Lund-Hoie & Bayer, 1968;Lund-Hoie & Bylterud, 1969), but there is some controversy about the form ir which aminotriazole is translocated. It is supposed to be translocated out ofthe leaf as an amine glucoside (Rogers, 1957;Herrett & Linck, 1961;Fredrick & Centile, 1960;Racusen, 1958) or in an activated form called Unknown III (Herrett & Bagley, 1964). However, in the coniferous species Abies concolor Hoopes and Pinus ponderosa Dougl.…”

Section: Introductionmentioning

confidence: 99%

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THE CORRELATION OF THE PHYTOCIDAL EFFECT OF 3‐AMlNO‐1,2,4‐TRlAZOLE WITH THE GROWTH STAGE OF OAT PLANTS

Lund‐Hoöie

1970

Weed Research

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Summary. Studies of the metabolic fate of aminotriazole in oat plants, cv. Condor, and the translocation patterns of aminotriazole, metabolites and carbohydrates were made to explain why oat plants at the 2–3‐leaf stage and plants at a later growth stage differ in susceptibility to aminotriazole. Using spot application of 3‐amino‐1,2,4‐triazole‐5−14Cand a method of exposing isolated leaves of oat plants to 14CO2, it was revealed that aminotriazole itself was translocated to negligible extent. There was rapid metabolism of aminotriazole in the leaves to a highly phytotoxic product, which appeared to be quite mobile within the plants. The tolerance of oat plants at the 2–3‐leaf stage to low rates of aminotriazole was caused by (1) a high detoxication rate of the phytotoxic metabolite at this stage, (2) a lesser accumulation of the phytotoxic product in the top leaf in plants at the 2–3‐Ieaf stage. Carbohydrates were used for comparison. The smaller accumulation could be explained by a high degree of cleavage of the aminotriazole‐14 C nucleus which in turn ended in evolution of 14CO2. In plants at the reproductive stage, these processes were considerably less obvious. The phytotoxic metabolite was degraded into three more products all of which appeared to be non‐toxic to oat and wheat plants. One of these products was found to accumulate in the seeds. A tendency for the phytotoxic metabolite to accumulate was also observed, especially when the aminotriazole was applied to oat plants at the reproductive stage. Corrélation de l'effet phytodde du 3‐amino‐1,2,4‐triazole avec le stade de croissance ds l'avoine Reésumeé. Des études sur les transformations meétaboliqucs de l'aminotriazole dans des avoines de la variété Condor, et sur les modaliteés de migration de l'aminotriazole, des meétabolites et des hydrates de carbone, ont eété entreprises pour expliquer pourquoi les avoines au stade 2/3 feuilles et à un stade de deéveloppement plus tardif preéntaient des différences de sensibilitéà l'aminotriazole. L'utilisation d'applications ponctuelles de 3‐amino‐1,2,4‐triazole‐5‐14C et d'une meéthode d'exposition des feuilles isolées d'avoine au 14CO2 montra que l'aminotriazole lui‐meême eétait transporteé en quantite négligeable dans les avoines. Ce fait fut expliqué par la métabolisation rapide de l'aminotriazole dans les feuilles et sa transformation en un produit extrêmement toxiquc, qui se révé1a treès mobile à l'apos;intérieur des plantes. La résistance des avoines au stade 2/3 feuilles à de faibles doses d'aminotriazote réault a (1) d'un taux élevé de détoxification du métabolite phytotoxique à ce stade, (2) d'une accumulation plus faible du produit phytotoxique dans la feuille supérieure des plantes, au stade 2/3 feuilles. Les hydrates de carbone furent utilisés pour la comparaison. L'accumulation plus faible pourrait être expliquée par un haut degré de clivage du noyau de l‘aminotriazole‐14C qui, à son tour, achève son évolution en 14CO 2. Dans les plantes au stade de la reproduction, ces processus furent beaucoup moin...

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Section: Metabolism Of Aminotriazole In Oatssupporting

confidence: 51%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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THE CORRELATION OF THE PHYTOCIDAL EFFECT OF 3‐AMlNO‐1,2,4‐TRlAZOLE WITH THE GROWTH STAGE OF OAT PLANTS

Lund‐Hoöie

1970

Weed Research

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“…Unknown II was also stable in 6N HCl for 5 h at lOO^C (Racusen, 1958). Herrett & Bagley (1964) reported that tbe metabolite Unknown III, isolated from Cirsium arvense, was more phytotoxic than aminotriazole and caused very fast discoloration and necrosis. It did not react with ninhydrin and it was readily hydrolysed.…”

Section: Properties Of Metabolite Amentioning

confidence: 99%

TRANSLOCATION OF ¹⁴C‐ASSIMILATES AND 3‐AMINO‐1,2,4‐TRIAZOLE AND ITS METABOLITES IN AGROPYRON REPENS

1972

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Summary. Translocation of 3‐amino‐1,2,4‐triazole‐5‐14C (14C‐aminotriazole) was compared to that of 14C‐assimilates in couch grass (Agropyron repens (L.) Beauv.) at three different growth stages. Assimilates of 14CO2 were translocated from the treated shoot to other shoots and rhizomes at the 2–3‐leaf and 3–4‐leaf stages of development. Much less labelled material was translocated into untreated shoots at the 5‐leaf stage. More 14C‐assimilates were translocated to the roots than to untreated shoots at all developmental stages. The translocation patterns of 14C‐aminotriazole and 14C‐assimilates were similar. Two metabolites, A and B, were formed from 14C‐aminotriazole, which chromatographed identically to previously described metabolites in Cirsium arvense (L.) Scop. A was further metabolized into B. Labelled aminotriazole and its two metabolites were translocated throughout the plants. Metabolite A was phytotoxic when concentrated and re‐applied to couch grass, but its properties were not those of Unknown II from Cirsium arvense. They were the same as those of Unknown III. Whether or not metabolite A and Unknown III are identical was not established. Migration des substances assimilables marquées au 14 C, du 3 amino‐1,2,4‐triazole et de ses métabolites chez Agropyron repens

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“…Since the discovery of 3-amino-l,2,4-triazole (aminotriazoie) as a herbicide and growth regulator (Hall, Johnson & Leinweber, 1954;Shaw & Swanson, 1953), the metabolism of this compound in various plant species has been studied by several workers (Carter, 1965;Carter & Naylor, 1960Fang, Fallin & Khanna, 1967;Fredrick & Gentile, 1965;Herrett & Bagley, 1964;Herrett & Linck, 1961;Massini, 1963;Miller & Hall, 1961;Racusen, 1958;Rogers, 1957;Shimabukuro & Linck, 1965;Smith, Bayer & Foy, 1968;Williams, Cox & Eagon, 1965). It has been reported that several metaljolites of aminotriazoie are formed rapidly in plants, but only two major metabolites (Unknown I and Unknown II) have received particular attention.…”

Section: Introductionmentioning

confidence: 99%

AMINOTRIAZOLE METABOLISM IN CIRSIUM ARVENSE (L.) SCOP. AND PISUM SATIVUM L.

Smith

Chang

1973

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Summary. Excised leaves as well as intact plants of Canada thistle (Cirsium arvense (L.) Scop.) metabolized 3‐amino‐l,2,4‐triazole (aminotriazole) to three major products, Unknowns II, 1a and 1b. Unknown II was identical to β‐(3‐amino‐l,2,4‐triazolyl‐l‐)α‐alanine. Unknowns 1a and 1b, previously described as one product, were separated by electrophoresis and thin layer chromatography. Unknown 1a appeared to be a metabolic product of Unknown II while Unknown 1B was derived from Unknown 1a. An enzyme preparation from pea (Pisum sativum L. cv. Thompson Laxton) seedlings capable of synthesizing tryptophan from indole and serine was also able to metabolize aminotriazole. Tryptophan synthesis with the enzyme preparation was inhibited by aminotriazole and evidence suggests that aminotriazole metabolism may follow a similar pathway to tryptophan synthesis. Métabolisme de l'aminotriazole chez Cirsium arvense (L.) Scop, et Pisum sativum L.

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Metabolism of Herbicides, Metabolism and Translocation of 3-Amino-1,2,4-triazole by Canada Thistle

Cited by 20 publications

References 2 publications

THE CORRELATION OF THE PHYTOCIDAL EFFECT OF 3‐AMlNO‐1,2,4‐TRlAZOLE WITH THE GROWTH STAGE OF OAT PLANTS

THE CORRELATION OF THE PHYTOCIDAL EFFECT OF 3‐AMlNO‐1,2,4‐TRlAZOLE WITH THE GROWTH STAGE OF OAT PLANTS

TRANSLOCATION OF ¹⁴C‐ASSIMILATES AND 3‐AMINO‐1,2,4‐TRIAZOLE AND ITS METABOLITES IN AGROPYRON REPENS

AMINOTRIAZOLE METABOLISM IN CIRSIUM ARVENSE (L.) SCOP. AND PISUM SATIVUM L.

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Metabolism of Herbicides, Metabolism and Translocation of 3-Amino-1,2,4-triazole by Canada Thistle

Cited by 20 publications

References 2 publications

THE CORRELATION OF THE PHYTOCIDAL EFFECT OF 3‐AMlNO‐1,2,4‐TRlAZOLE WITH THE GROWTH STAGE OF OAT PLANTS

THE CORRELATION OF THE PHYTOCIDAL EFFECT OF 3‐AMlNO‐1,2,4‐TRlAZOLE WITH THE GROWTH STAGE OF OAT PLANTS

TRANSLOCATION OF 14C‐ASSIMILATES AND 3‐AMINO‐1,2,4‐TRIAZOLE AND ITS METABOLITES IN AGROPYRON REPENS

AMINOTRIAZOLE METABOLISM IN CIRSIUM ARVENSE (L.) SCOP. AND PISUM SATIVUM L.

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TRANSLOCATION OF ¹⁴C‐ASSIMILATES AND 3‐AMINO‐1,2,4‐TRIAZOLE AND ITS METABOLITES IN AGROPYRON REPENS