Synthesis, crystal structure, and herbicidal activity of pyrimidinyl benzylamine analogues containing a phosphonyl group

Tang, Wu; Yu, Zhi-Hua; Shi, Dashuang

doi:10.1002/hc.20589

Cited by 33 publications

(13 citation statements)

References 15 publications

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“…Ia−Ir are known compounds, and their spectra data can also be found in the literature. 32 Data Results from testing on the GH2 screen, with positive controls. Scores are given as percent phytotoxicity score.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Synthesis and Biological Activity Evaluation of Novel α-Amino Phosphonate Derivatives Containing a Pyrimidinyl Moiety as Potential Herbicidal Agents

Chen

Tang

Che

et al. 2015

J. Agric. Food Chem.

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To find novel high-activity and low-toxicity herbicide lead compounds with novel herbicidal mode of action, series of novel α-amino phosphonate derivatives containing a pyrimidinyl moiety, I, II, III, and IV, were designed and synthesized by Lewis acid (magnesium perchlorate) catalyzed Mannich-type reaction of aldehydes, amines, and phosphites. Their structures were clearly identified by spectroscopy data (IR, (1)H NMR, (31)P NMR, EI-MS) and elemental analyses. The bioassay [in vitro, in vivo (GH1 and GH2)] showed that most compounds I exhibited good herbicidal activities; for example, the activities of compounds Ib, Ic, Ig, Ii, Ik, and Im were as good as the positive control herbicides (acetochlor, atrazine, mesotrione, and glyphosate). However, their structural isomers II and III and analogues IV did not display any herbicidal activities in vivo, although some of them possessed selective inhibitory activity against Arabidopsis thaliana in vitro. Interestingly, it was found that compounds IVs, IVt, and IVl showed selective insecticidal activities against Aphis species or Plutella xylostella, respectively. Their preliminary herbicidal mode of action and structure-activity relationships were also studied.

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Section: ■ Materials and Methodsmentioning

confidence: 99%

Synthesis and Biological Activity Evaluation of Novel α-Amino Phosphonate Derivatives Containing a Pyrimidinyl Moiety as Potential Herbicidal Agents

Chen

Tang

Che

et al. 2015

J. Agric. Food Chem.

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“…[27,28] The Pyrimidines containing α-aminophosphonate skeleton are of great interest according to their herbicidal activities. [16] Thus, diethyl chromonyl α-aminophosphonate 1 was reacted with thiourea, guanidinium carbonate and cyanoguanidine as 1,3-bi-nucleophiles in ethanolic sodium ethoxide to yield the corresponding pyrimidinyl α-aminophosphonates 14−16, respectively (Scheme 6).…”

Section: Methodsmentioning

confidence: 99%

“…[10] α-Aminophosphonates containing five-and six-membered heterocycles at α-position are known. [11][12][13][14][15][16] To the best our knowledge, α-aminophosphonates possess sevenmembered heterocycles at α-position have not been reported hitherto. Moreover a basic difficulty in the synthesis of parent α-heterocyclic α-aminophosphonate is an applicability of known regular procedures for synthesis of the typical α-aminophosphonates.…”

Section: Introductionmentioning

confidence: 99%

Cleavage of Diethyl Chromonyl α-Aminophosphonate with Nitrogen and Carbon Nucleophiles: A Synthetic Approach and Biological Evaluations of A Series of Novel Azoles, Azines and Azepines Containing α-Aminophosphonate and Phosphonate Groups

Ali

Abdel‐Aziz

El-Edfawy

et al. 2014

Proceedings of the 18th International Electronic Conference on Synthetic Organic Chemistry

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A convenient synthetic approach leading to synthesize a series of novel substituted azoles, azines and azepines linked to α-aminophosphonate moiety was achieved. The methodology depends on ring-opening and ring-closure (RORC) of chromone ring of diethyl chromonyl α-aminophosphonate 1 via its reaction with nitrogen nucleophiles such as primary amines, 1,2-, 1,3-and 1,4-bi-nucleophiles in ethanolic sodium ethoxide. Also, treatment of compound 1 with some acyclic and cyclic active methylene compounds under the same reaction conditions afforded interesting novel isolated and fused pyridine systems bearing phosphonate groups at α-position. The screening of antimicrobial activity for the synthesized compounds indicates that connection of pyrazole, oxazepine and benzodiazepine rings with α-aminophosphonate moiety exhibited good antimicrobial effects. Also, evaluation of their antioxidant properties exemplifies that the compounds having 1,5benzoxazepinyl and 1,5-benzodiazepinyl units in combination with α-aminophosphonic diester moiety are the most powerful antioxidant agents.

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“…A distinct advantage of EPM as a weedicide is that, this compound has an herbicidal activity 1.5-2 times higher and requires an application rate 1/5-1/10 lower than bensulfuron-methyl (a broad-spectrum herbicide) on Echinochloa crusgalli and Leptochloa chinensis (Iwakami et al 2015;Shibayama 2001;Song et al 2010). Notably, EPM can prevent the growth of E. crusgalli and L. chinensis populations and suppress them effectively over long periods, while being non-toxic, and eventually increasing the yield of paddy rice and subsequent crops (e.g., rape, cabbage, Astragalus smicus, wheat, and potato) (Iwafune et al 2010;Qin et al 2017;Tang et al 2010;Yoshii et al 2020). Nevertheless, few studies have lucubrated the environmental behaviors of EPM after it was widely used as herbicide in the farming industry.…”

Section: Introductionmentioning

confidence: 99%

Environmental Behaviors of (E)-Pyriminobac-methyl in Agricultural Soils

Zhou

Jia

et al. 2021

Preprint

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(E)-Pyriminobac-methyl (EPM), a pyrimidine benzoic acid esters herbicide, has a high potential as weedicide; nevertheless, its environmental behaviors are still not well understood. In this study, we systematically investigated for the first time the adsorption–desorption, degradation, and leaching behaviors of EPM in agricultural soils from five exemplar sites in China (characterized by different physicochemical properties) through laboratory simulation experiments. The EPM adsorption–desorption results were well fitted by the Freundlich model (R2 > 0.9999). In the analyzed soils, the Freundlich adsorption (i.e., Kf-ads) and desorption (i.e., Kf-des) coefficients of EPM varied between 0.85–32.22 mg1−1/n L1/n kg−1 and between 0.78–5.02 mg1−1/n L1/n kg−1, respectively. Moreover, the degradation of EPM reflected first-order kinetics: its half-life ranged between 37.46–66.00 d depending on the environmental conditions, and abiotic degradation was predominant in the degradation of this compound. The mobility of EPM in the five soils varied from immobile to highly mobile. The groundwater ubiquity score ranged between 0.9765–2.7160, indicating that EPM posed threat to groundwater quality. Overall, the results of this study demonstrate the easy degradability of EPM, as well as its high adsorption affinity and low mobility in soils with abundant organic matter content and high cation exchange capacity. Under such conditions, there is a relatively low contamination risk for groundwater systems in relation to this compound. Overall, our findings provide a solid basis for predicting the environmental impacts of EPM.

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Synthesis, crystal structure, and herbicidal activity of pyrimidinyl benzylamine analogues containing a phosphonyl group

Abstract: A series of pyrimidinyl benzylamine analogues containing a phosphonyl group (2)

Cited by 33 publications

References 15 publications

Synthesis and Biological Activity Evaluation of Novel α-Amino Phosphonate Derivatives Containing a Pyrimidinyl Moiety as Potential Herbicidal Agents

Synthesis and Biological Activity Evaluation of Novel α-Amino Phosphonate Derivatives Containing a Pyrimidinyl Moiety as Potential Herbicidal Agents

Cleavage of Diethyl Chromonyl α-Aminophosphonate with Nitrogen and Carbon Nucleophiles: A Synthetic Approach and Biological Evaluations of A Series of Novel Azoles, Azines and Azepines Containing α-Aminophosphonate and Phosphonate Groups

Environmental Behaviors of (E)-Pyriminobac-methyl in Agricultural Soils

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