141-83-3Relevant articles and documents
Aerobic soil metabolism of metsulfuron-methyl
Li,Zimmerman,Gorman,Reiser,Fogiel,Haney
, p. 434 - 445 (1999)
A laboratory study was conducted to determine the degradation rates and identify major metabolites of the herbicide metsulfuron-methyl in sterile and non-sterile aerobic soils in the dark at 20°C. Both [phenyl-U-14C]- and [triazine-2-14C]metsulfuron-methyl were used. The soil was treated with [14C]metsulfuron-methyl (0.1 mg kg-1) and incubated in flow-through systems for one year. The degradation rate constants, DT50, and DT90 were obtained based on the first-order and biphasic models. The DT50 (time required for 50% of applied chemical to degrade) for met sulfuron-methyl, estimated using a biphasic model, was approximately 10 days (9-11 days, 95% confidence limits) in the non-sterile soil and 20 days (12-32 days, 95% confidence limits) in the sterile soil. One-year cumulative carbon dioxide accounted for approximately 48% and 23% of the applied radioactivity in the [phenyl-U-14C] and [triazine-2-14C]metsulfuron-methyl systems, respectively. Seven metabolites were identified by HPLC or LC/MS with synthetic standards. The degradation pathways included O-demethylation, cleavage of the sulfonylurea bridge, and triazine ring opening. The triazine ring-opened products were methyl 2- [[[[[[[(acetylamino)carbonyl]amino]carbonyl]amino] carbonyl]- amino]sulfonyl]benzoate in the sterile soil and methyl 2- 1[[[[[amino](aminocarbonyl)imino]methyl] amino]carbonyl]amino]sulfonyl]benzoate in the non-sterile soil, indicating that different pathways were operable.
Anionic amidinourea-metal(II) tautomers: MN2O2or MN4?
Hatanaka, Masashi
, p. 162 - 172 (2015)
Structures of amidinourea-metal complexes have been obscured by subtle tautomerism and crystal waters. To clarify the most stable form of the tautomers, bis(amidinourea)copper(II) anhydride and the alkyl derivatives were synthesized under basic conditions, and the stability of the CuN2O2 chromophore was suggested. From substituent effects of chelations, UV-vis spectra, IR/Raman spectra, and DFT calculations, it was suggested that the bis(amidinourea)copper-(II) has a CuN2O2 chromophore, not CuN4 chromophore. The mutual exclusion rule of IR/Raman spectra supported the trans-CuN2O2 chromophore. Systematic calculations on bis(amidinourea)-Cu(II), -Ni(II), -Pd(II), -Zn(II), and -Cd(II) chelates revealed that the robust stability of CuN2O2 chromophores originates from quasi aromaticity in the six-membered chelate rings. cis- or trans-CuN4 stability reported in the early references is suspicious.
Kinetics and mechanism of oxidation of metformin hydrochloride by hexamolybdocobaltate(III) in acidic medium
Sawant,Patil,Gokavi
, p. 15 - 20 (2021/01/06)
The oxidation of metformin hydrochloride by Anderson-Evans type hexamolybdocobaltate(III) anion was investigated under pseudo-first-order condition in acidic medium at 298 K. The rate of reaction is accelerated by increase in the concentration of H+ ion. The decrease in the reaction rate with increase in the concentration of the oxidant [H6CoMo6O24]3- anion and added molybdate ion kinetically indicate existence of the prior equilibria between various forms of the oxidant. In present study, the oxidant exists in monomers [H6CoMo6O24]3-anion, [H5CoMo5O20]2- anion and dimer [H4Co2Mo10O38]6- forms between the pH 2 and 1. The active oxidant species is [H5CoMo5O20]2-anion. Under experimental conditions, the reaction involves direct electron-transfer from metformin center to oxidant anion generating free radical in rate determining step. The fast hydrolysis of formed free radical in presence of second oxidant molecule leads to formation of carbonyl imino functional group in the oxidation product. The ionic strength and solvent polarity had no significant effect on the rate of reaction. FT-IR spectra of metformin and its oxidation product sample were recorded and analyzed. The FT-IR spectra show the change in frequency of the functional groups of oxidation product than that of the pure MET. The formation of oxidation product was confirmed by high performance liquid chromatography associated with electron impact mass spectroscopy (LC/EI-MS). Thermodynamic parameters are evaluated by temperature variation kinetic data and are in support of the proposed mechanism. The probable mechanism is proposed leading to complicated rate law as a result of involvement of prior equillibria between various forms of the oxidant.
Retinoidal pyrimidinecarboxylic acids. Unexpected diaza-substituent effects in retinobenzoic acids
Ohta, Kiminori,Kawachi, Emiko,Inoue, Noriko,Fukasawa, Hiroshi,Hashimoto, Yuichi,Itai, Akiko,Kagechika, Hiroyuki
, p. 1504 - 1513 (2007/10/03)
Several pyridine- and pyrimidine-carboxylic acids were synthesized as ligand candidates for retinoid nuclear receptors, retinoic acid receptors (RARs) and retinoic X receptors (RXRs). Although the pyridine derivatives, 6-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl]pyridine- 3-carboxylic acid (2b) and 6-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carboxamido]pyridin e-3-carboxylic acid (5b) are more potent than the corresponding benzoic acid-type retinoids, Am80 (2a) and Am580 (5a), the replacement of the benzene ring of Am580 (5a), Am555 (6a), or Am55 (7a) with a pyrimidine ring caused loss of the retinoidal activity both in HL-60 cell differentiation assay and in RAR transactivation assay using COS-1 cells. On the other hand, pyrimidine analogs (PA series, 10 and 11) of potent RXR agonists (retinoid synergists) with a diphenylamine skeleton (DA series, 8 and 9) exhibited potent retinoid synergistic activity in HL-60 cell differentiation assay and activated RXRs. Among the synthesized compounds, 2-[N-n-propyl-N-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)amino] pyrimidine-5-carboxylic acid (PA013, 10e) is most active retinoid synergist in HL-60 assay.
Mechanism of Reactions of Some N1-Substituted Biguanides with Chromium(VI) in Aqueous Sulphuric Acid Media
Banerjee, Rupendranath,Bhattacharya, Anamika,Das, Prabir K.,Chakraburtty, Amiya K.
, p. 1557 - 1560 (2007/10/02)
N1-Phenylbiguanide RHN-C(=X)NH-C(=NH)NH2 (R=Ph, X=NH) reacts quantitatively in aqueous sulphuric acid media with CrVI and CeIV to produce 1,4-benzoquinone, carbamimidoylurea (R=H, X=O), and ammonium ion.N1-(4-Methoxyphenyl)biguanide (R=4-MeOC6H4, X=NH) reacts similarly except that, instead of a quinone, more extensively oxidized products are produced.Phenylbiguanide (pbg) itself, in acid solution, undergoes slow hydrolysis, and anilinium ion is one of the products.The hydrolyzed solution reacts rapidly with CrVI and CeIV.None of the other six biguanides investigated and three other structurally related compounds reacts with CrVI under the experimental conditions.The kinetics of the reactions is in accord with the rate law (i).A typical (i) value of k is (0.25 +/- 0.03)*10-5 s-1 at 20 deg C, =1.0 mol dm-3, and / =2.0 mol dm-3, and when determined from experiments with an excess of CrVI (first-order kinetics observed) agrees closely with that determined in the presence of an excess of pbg (zero-order kinetics) and also that determined for reactions with CeIV.These results have been interpreted in terms of a mechanism involving the acid-promoted hydrolysis of phenylbiguanide , the oxidant functioning as an analytical assay of the anilinium product.
Heterocyclic amidino substituted ureas and their pharmaceutical uses
-
, (2008/06/13)
This invention relates to methods for the prophylactic and curative treatment of gastrointestinal and cardiovascular disorders and parasitic infections in humans and animals, using a class of hetrocyclic amidino substituted urea and thiourea compounds, a novel class of heterocyclic amidino substituted urea and thiourea compounds and pharmaceutical compositions and animal feed additives including the same.
Platinum complexes of antitumor agents
-
, (2008/06/13)
Platinum chelates of substituted hydrazine car-boximidamides which are useful as antitumor agents.
Platinum complexes of antitumor agents
-
, (2008/06/13)
The compounds are the class of substituted hydrazine carboximidamides which are useful for inducing the regression and/or palliation of leukemia and related cancers in mammals when administered in amounts of from about one mg. to about 1.2 gm. per square meter of body surface area per day.
Synthesis of Guanidino-1,3,5-triazines Using DMF
Iio, Kokoro,Ichikawa, Eiichi
, p. 2735 - 2736 (2007/10/02)
2,4,6-Triguanidino-1,3,5-triazine and 2,4,6-tris(3-methylguanidino)-1,3,5-triazine were synthesized in 42 and 52percent yields, respectively, by the cyclotrimerization of cyanoguanidine and 1-methyl-3-cyanoguanidine using DMF as a solvent in the presence of hydrogen chloride. 1-Phenyl-3-cyanoguanidine, 1,2-dimethyl-3-cyanoguanidine, and 2-imidazolidinylidenecyanamide, however, were cyclodimerized to the corresponding guanidino-1,3,5-triazines in a similar manner.
