Excretion balance, metabolic fate, and tissue residues following treatment of rats with thidiazuron cotton defoliant

Crecelius, Cheryl S.; Knowles, Charles O.

doi:10.1021/jf60216a010

Cited by 11 publications

(28 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The major metabolites formed were glucosides, derived from either direct glucosylation of thidiazuron or via hydroxylation and subsequent glycosylation at the para-position of the phenyl ring. Although the metabolism of thidiazuron in plant systems has not been reported previously, studies have been performed with animals such as rats and goats where the major metabolites obtained were 4-hydroxyphenyltbidiazuron and phenylurea (Benezet et al 1978, Crecelius andKnowles 1978). In a study of the metabolism of N,N'-diphenylurea (a weakly active phenylurea-type cytokinin) in tobacco tissues, the only metabolite identified contained a glucosyl substitution at the phenyl ring (Burrows and Leworthy 1976).…”

Section: Discussionmentioning

confidence: 99%

“…In a study of the metabolism of N,N'-diphenylurea (a weakly active phenylurea-type cytokinin) in tobacco tissues, the only metabolite identified contained a glucosyl substitution at the phenyl ring (Burrows and Leworthy 1976). Thus it appears that hydroxylation of the phenyl ring of phenylurea compounds is a common feature in both animal and plant systems, but cleavage of the urea bridge (Benezet et al 1978, Crecehus andKnowles 1978) or glucosylation (present data) is more specific for certain types of organisms.…”

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

The metabolism of [¹⁴C]‐tMdiaziiroii in callus tissues of Phaseolus lunatus

Mok

1985

Physiologia Plantarum

View full text Add to dashboard Cite

The metabolism of [14C]‐thidiazuron (N‐phenyl‐N'‐l,2,3‐tbiadiazol‐5‐ylurea), a compound with extremely high cytokinin activity, was examined in callus cultures of Phaseolus lunatus L. cv. Kingston. No appreciable metabolism of the compound was detected in short‐term studies (up to 48 h). When tissues were grown on medium containing [14C]‐thidiazuron for longer periods (12 to 33 days), several major metabolites were isolated. The array of radioactive metabolites was the same using [14C]‐thidiazuron with the label in the phenyl ring, the urea bridge or the thiadiazol ring, indicating no degradation of the thidiazuron molecule. Enzyme digestion followed by HPLC and TLC analyses was used to identify major metabolites. α‐Gtacosidase degraded two of the metabolites to thidiazuron and a third was converted to N‐p‐hydroxyphenyl‐N2‐l,2,3‐thiadiazol‐5‐ylurea. Limited tests of the O‐glycosyl derivatives for cytokinin activity indicated that they are much less active than the parent compound. Bioassays involving hydroxylated derivatives of thidiazuron indicated that the p‐hydroxyphenyl derivative was 10000 limes less active than the parent compound, and the oetho‐ and mete‐derivatives had 1000 and 100 times lower activity, respectively, than thidiazuron. These results suggest that thidiazuron itself is the active compound and that metabolism of thidiazuron in Phaseolus tissues only involves modification of the intact structure, yielding metabolites that are less cytokinin‐active.

show abstract

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

The metabolism of [¹⁴C]‐tMdiaziiroii in callus tissues of Phaseolus lunatus

Mok

1985

Physiologia Plantarum

View full text Add to dashboard Cite

show abstract

“…Heart, brain, spleen, uterus, fat, and muscle contained <100 ppb. By the seventh day on untreated food more than 50% of the radiocarbon in the tissues had cleared (Crecelius and Knowles, 1978). Radiocarbon-containing residues in tissues 14 from goats and hens treated with multiple doses of thidiazuron-C also were low .…”

Section: Mammalian Metabolism Of Substituted Urea Pesticidesmentioning

confidence: 98%

“…14 Tissues from rats treated with a single oral dose of thidiazuron-Chad 7 <20 ppb of radiocarbon (Crecelius and Knowles, 1978). Tissue residues in 14 rats on a dietary supplement of 6.6 ppm of thidiazuron-C for 9 days showed a rapid increase at the onset of the experiment followed by a plateau which remained until rats were replaced on an untreated diet.…”

Section: Mammalian Metabolism Of Substituted Urea Pesticidesmentioning

confidence: 99%

See 1 more Smart Citation

Excretion balance, metabolic fate, and tissue residues of N-Phenyl-N'-1,2,5-Thiadiazol-3-Ylurea (Photothidiazuron) in rats

Johnson¹

View full text Add to dashboard Cite

"Thidiazuron (DROPP[copyright]) or N-phenyl-N'-1,2,3-thiadiazol-5-ylurea is a promising new cotton defoliant currently being developed by NOR-AM Agricultural Products, Incorporated. In addition to its defoliating activity, thidiazuron demonstrates strong inhibition of regrowth with no adverse effect on the opening or quality of fiber of mature bolls not open at the time of application (Anonymous, 1975). These attributes indicate this could be a useful product. With the possibility of widespread use of thidiazuron in cotton growing regions, it is necessary to consider the result of its photodegradation. The major thidiazuron conversion product, which occurs on the plant surface, is photothidiazuron or N-phenyl-N'-1,2,5-thiadiazol-3-ylurea (Anonymous, 1976). This new compound is the result of a rearrangement in the thiadiazol moiety (Anonymous, 1976). Thidiazuron and photothidiazuron are classified chemically as substituted ureas. This includes a broad group of compounds varying greatly in their molecular substituents and commercial uses. However, most substituted ureas are herbicides, and therefore, the orientation of research has been directed to plant and soil situations. Research data pertaining to the effects of substituted ureas upon mammalian and other animal systems is very limited (Geissbuhler, et al., 1975). Since it is possible that leaves and other parts of a thidiazuron treated cotton plant may be incorporated into livestock feed or eaten by other animals, it is essential to examine certain of the properties of photothidiazuron in relation to mammalian systems. The purpose of this study was to determine the excretion balance, metabolic fate, and tissue residues of photothidiazuron in rats. Specifically, the objectives were: 1. To determine the excretion balance, metabolic fate, and tissue residues after the administration of a single oral dose of photothidiazuron-14 aniline- C to male rats, 2. To investigate the degradation of photothidiazuron by rat liver subcellular fractions and by a model hydroxylation system, and 3. To identify major photothidiazuron metabolites."--Introduction.

show abstract

Excretion balance, metabolic fate, and tissue residues ofN-phenyl-N?-1,2,5-thiadiazol-3-ylurea (photothidiazuron) in rats

Johnson

Knowles

1979

Arch. Environ. Contam. Toxicol.

View full text Add to dashboard Cite

Excretion balance, metabolic fate, and tissue residues following treatment of rats with thidiazuron cotton defoliant

Cited by 11 publications

References 4 publications

The metabolism of [¹⁴C]‐tMdiaziiroii in callus tissues of Phaseolus lunatus

The metabolism of [¹⁴C]‐tMdiaziiroii in callus tissues of Phaseolus lunatus

Excretion balance, metabolic fate, and tissue residues of N-Phenyl-N'-1,2,5-Thiadiazol-3-Ylurea (Photothidiazuron) in rats

Excretion balance, metabolic fate, and tissue residues ofN-phenyl-N?-1,2,5-thiadiazol-3-ylurea (photothidiazuron) in rats

Contact Info

Product

Resources

About

Excretion balance, metabolic fate, and tissue residues following treatment of rats with thidiazuron cotton defoliant

Cited by 11 publications

References 4 publications

The metabolism of [14C]‐tMdiaziiroii in callus tissues of Phaseolus lunatus

The metabolism of [14C]‐tMdiaziiroii in callus tissues of Phaseolus lunatus

Excretion balance, metabolic fate, and tissue residues of N-Phenyl-N'-1,2,5-Thiadiazol-3-Ylurea (Photothidiazuron) in rats

Excretion balance, metabolic fate, and tissue residues ofN-phenyl-N?-1,2,5-thiadiazol-3-ylurea (photothidiazuron) in rats

Contact Info

Product

Resources

About

The metabolism of [¹⁴C]‐tMdiaziiroii in callus tissues of Phaseolus lunatus

The metabolism of [¹⁴C]‐tMdiaziiroii in callus tissues of Phaseolus lunatus