Synthesis of hydrazine derivatives as plant growth inhibitors

Huffman, C. W.; Godar, Edith M.; Ohki, Kenneth.; Torgeson, Dewayne C.

doi:10.1021/jf60160a035

Cited by 25 publications

(10 citation statements)

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“…Hydrazide fragments, the important natural nitrogenous substructures that easily form hydrogen bonds with various biological enzymes, are found in many bioactive compounds with antibacterial, anticancer, anticoagulant, anti‐inflammatory, antifungal, antimalarial, antiviral, insecticidal or herbicidal property. In the last decade, the studies on synthesis and agricultural bioactivity of hydrazide derivatives have attracted considerable attentions .…”

Section: Introductionmentioning

confidence: 99%

“…Strikingly, Zhang et al verified the antifungal mechanism of 3-acylaminoquinazolinone derivatives as chitinase inhibitors, and found a carbonyl group at the N-3 position of quinazolin-4(3H)-one nucleus plays a key role in inhibiting chitinous biosynthesis. [15] Hydrazide fragments, the important natural nitrogenous substructures that easily form hydrogen bonds with various biological enzymes, [20] are found in many bioactive compounds with antibacterial, [21] anticancer, [22] anticoagulant, [23] anti-inflammatory, [24] antifungal, [25] antimalarial, [26] antiviral, [27] insecticidal [28] or herbicidal [29] property. In the last decade, the studies on synthesis and agricultural bioactivity of hydrazide derivatives have attracted considerable attentions.…”

Section: Introductionmentioning

confidence: 99%

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Design, Synthesis and 3D‐QSAR of New Quinazolin‐4(3H)‐one Derivatives Containing a Hydrazide Moiety as Potential Fungicides

Wang

Yan

et al. 2018

ChemistrySelect

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A series of quinazolin‐4(3H)‐one derivatives containing a hydrazide moiety were designed, synthesized and characterized in detail via FT‐IR, 1H NMR, 13C NMR and HRMS spectra. The antifungal activities against Rhizoctonia solani (Rs) and Fusarium graminearum (Fg) were evaluated in vitro. The bioassay results indicated that most of the title compounds exhibited significant antifungal activities against Rs and Fg. Strikingly, the EC50 values of some title compounds against Rs are obviously superior to that of the positive control carbendazim. Based on the antifungal bioassay results against Rs, the comparative molecular filed analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA) models were generated to investigate the structure‐activity relationship of title compounds against Rs. The analytical results indicated that these two models exhibited good predictive accuracies and could provide significant structural insights for the design of bioactive quinazolin‐4(3H)‐one derivatives containing a hydrazide moiety.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and 3D‐QSAR of New Quinazolin‐4(3H)‐one Derivatives Containing a Hydrazide Moiety as Potential Fungicides

Wang

Yan

et al. 2018

ChemistrySelect

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“…Because of the significant value in pharmaceuticals, the synthesis and bioactivity of 4(3 H )-quinazolinone and its derivatives have drawn considerable interest. On the other hand, hydrazide has been widely used as a functional fragment in drug design owing to a lot of its derivatives exhibiting various bioactivities, such as anticancer, antibacterial, antifungal, insecticidal, and herbicidal activities. Tebufenozide and chromafenozide (Figure ) are two compounds bearing a hydrazide group, which have been launched as commercial insecticides …”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Structure–Activity Relationship of Quinazolinone Derivatives as Potential Fungicides

Peng

Yin

et al. 2021

J. Agric. Food Chem.

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Plant diseases caused by phytopathogenic fungi reduce the yield and quality of crops. To develop novel antifungal agents, we designed and synthesized eight series of quinazolinone derivatives and evaluated their anti-phytopathogenic fungal activity. The bioassay results revealed that compounds KZL-15, KZL-22, 5b, 6b, 6c, 8e, and 8f exhibited remarkable antifungal activity in vitro. Especially, compound 6c displayed the highest bioactivity against Sclerotinia sclerotiorum, Pellicularia sasakii, Fusarium graminearum, and Fusarium oxysporum, displaying appreciable IC50 values (50% inhibitory concentration) of 2.46, 2.94, 6.03, and 11.9 μg/mL, respectively. A further mechanism interrogation revealed abnormal mycelia, damaged organelles, and changed permeability of cell membranes in S. sclerotiorum treated with compound 6c. In addition, the in vivo bioassay indicated that compound 6c possessed comparable curative and protective effects (87.3 and 90.7%, respectively) to the positive control azoxystrobin (89.5 and 91.2%, respectively) at 100 μg/mL concentration against S. sclerotiorum. This work validated the potential of compound 6c as a new and promising fungicide candidate, contributing to the exploration of potent antifungal agents.

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“…Hydrazine (N 2 H 4 ) is an important biochemical reagent, which can be used as a metal corrosion inhibitor (Cruz Vieira et al 2002), antibacterial drugs (Balsamo et al 1983), plant growth regulators (Huffman et al 1968), hydrazine fuel cell (Serov and Kwak 2010), and be used in rocket propulsion Propellant system (Zelnick Sanford et al 2003;Mo et al 2000). It is widely used in various chemical industries.…”

Section: Introductionmentioning

confidence: 99%

A multi-responsive coumarin–benzothiazole fluorescent probe for selective detection of biological thiols and hydrazine

Chen

Shang

et al. 2021

J Anal Sci Technol

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Biothiols play important roles in various physiological and biological processes, which closely related to many diseases. Hydrazine is widely used in the chemical industry, but it is harmful to humans and animals. Therefore, it is very important to develop a fluorescent probe that can simultaneously detect biological thiols and hydrazine. In this work, a new fluorescent probe (2E,4Z)-2-(benzo[d]thiazol-2-yl)-5-chloro-5-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)penta-2,4-dienenitrile (BCD) was synthesized by integrating coumarin and benzothiazole acetonitrile. Featured with four binding sites and different bonding mechanism between probe with biothiols and hydrazine, this probe exhibited fluorescent turn-on for distinguishing Cys, Hcy, GSH and hydrazine with 760-, 8-, 6- and 637-fold fluorescent intensity increase at 502, 479, 476 and 458 nm, respectively, through different excitation wavelengths. Research on the effect of pH on the fluorescent performance of BCD shows that the probe exhibits superior stability in a weakly alkaline to weakly acidic environment, which will facilitate the detection of biological thiols or hydrazine hydrate by BCD. Selectivity studies have shown that the probe has high specificity to biological thiols and hydrazine, which is of great significance to the application of BCD.

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Synthesis of hydrazine derivatives as plant growth inhibitors

Cited by 25 publications

References 1 publication

Design, Synthesis and 3D‐QSAR of New Quinazolin‐4(3H)‐one Derivatives Containing a Hydrazide Moiety as Potential Fungicides

Design, Synthesis and 3D‐QSAR of New Quinazolin‐4(3H)‐one Derivatives Containing a Hydrazide Moiety as Potential Fungicides

Design, Synthesis, and Structure–Activity Relationship of Quinazolinone Derivatives as Potential Fungicides

A multi-responsive coumarin–benzothiazole fluorescent probe for selective detection of biological thiols and hydrazine

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