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Synthesis, insecticidal, and antibacterial activities of novel neonicotinoid analogs with dihydropyridine.

He Y, Hu D, Lv M, Jin L, Wu J, Zeng S, Yang S, Song B - Chem Cent J (2013)

Bottom Line: A synthetic route to obtain neonicotinoid analogs with dihydropyridine by the reaction of intermediates 2 (pyridyl (thiazolyl) methyl-2-substituted-methyl-ideneimidazolidine) and intermediates 1 (cyanoacrylates) and different aromatic aldehydes in acetonitrile under reflux conditions is presented.The effects of different solvents, bases, and reaction time on the reaction of 3a were investigated.The results of this study suggest that neonicotinoid analogs with dihydropyridine could cause N. lugens death and restrain P. solanacearum growth.

View Article: PubMed Central - HTML - PubMed

Affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang, China. basong@gzu.edu.

ABSTRACT

Background: Nilaparvata lugens, a major pest in rice-growing areas, is extremely difficult to manage. Neonicotinoids have increasingly been used in crop protection and animal health care against N. lugens. To discover new bioactive molecules and pesticides, we combined the active structure of cyanoacrylates, aromatic aldehydes, and substituted pyridyl (thiazolyl) methyl-2-substituted-methylidene-imidazolidine derivatives for the design and synthesis of a series of novel neonicotinoid analogs with dihydropyridine.

Results: A series of neonicotinoid analogs with dihydropyridine were synthesized. Their structures were characterized by IR, 1H NMR, 13C NMR, and elemental analysis and their insecticidal and antibacterial activities were assessed. Preliminary biological activity tests showed that all of the title compounds feature insecticidal activities against N. lugens at 500 mg/L. Moreover, some compounds showed promising antibacterial activities against Pseudomonas solanacearum (e.g., Tobacco bacterial wilt and Tomato bacterial wilt) at a dose of 200 mg/L.

Conclusion: A synthetic route to obtain neonicotinoid analogs with dihydropyridine by the reaction of intermediates 2 (pyridyl (thiazolyl) methyl-2-substituted-methyl-ideneimidazolidine) and intermediates 1 (cyanoacrylates) and different aromatic aldehydes in acetonitrile under reflux conditions is presented. The effects of different solvents, bases, and reaction time on the reaction of 3a were investigated. The results of this study suggest that neonicotinoid analogs with dihydropyridine could cause N. lugens death and restrain P. solanacearum growth.

No MeSH data available.


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Synthetic route to the title compounds 3.
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C1: Synthetic route to the title compounds 3.

Mentions: Neonicotinoid insecticides have many mutual molecular characteristics. The presence of a strong electron-withdrawing pharmacophoric group, such as CN or NO2, is an essential structural characteristic of these insecticides [21,22]. Amide derivatives have shown promising insecticidal activity [23-26]. In our previous work, we synthesized cyanomethylene heterocycles, such as compound V (Figure 1), by the reaction of different cyanoacrylate derivatives with N-((6-chloropyridin-3-yl) methyl) ethane-1,2-diamine, yielding several compounds that showed good insecticidal activity [27]. The elementary structure of CH-IMI was maintained and the cyclization gain pyridine ring involved an amide moiety. Based on these results, neonicotinoid analogs with dihydropyridine were prepared (Scheme 1). All of the compounds were characterized by IR, 1H NMR, 13C NMR, and elemental analysis. Preliminary biological evaluations revealed that most of the compounds exhibit insecticidal activity against N. lugens. Compounds 3a, 3c, and 3e exhibited ≥90.3% activity at a dose of 500 mg/L. Moreover, some of the compounds showed promising antibacterial activities against Pseudomonas solanacearum. Compound 3a showed particularly potent antibacterial activity that reached 88.1% against tomato bacterial wilt at a dose of 200 mg/L.


Synthesis, insecticidal, and antibacterial activities of novel neonicotinoid analogs with dihydropyridine.

He Y, Hu D, Lv M, Jin L, Wu J, Zeng S, Yang S, Song B - Chem Cent J (2013)

Synthetic route to the title compounds 3.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3649916&req=5

C1: Synthetic route to the title compounds 3.
Mentions: Neonicotinoid insecticides have many mutual molecular characteristics. The presence of a strong electron-withdrawing pharmacophoric group, such as CN or NO2, is an essential structural characteristic of these insecticides [21,22]. Amide derivatives have shown promising insecticidal activity [23-26]. In our previous work, we synthesized cyanomethylene heterocycles, such as compound V (Figure 1), by the reaction of different cyanoacrylate derivatives with N-((6-chloropyridin-3-yl) methyl) ethane-1,2-diamine, yielding several compounds that showed good insecticidal activity [27]. The elementary structure of CH-IMI was maintained and the cyclization gain pyridine ring involved an amide moiety. Based on these results, neonicotinoid analogs with dihydropyridine were prepared (Scheme 1). All of the compounds were characterized by IR, 1H NMR, 13C NMR, and elemental analysis. Preliminary biological evaluations revealed that most of the compounds exhibit insecticidal activity against N. lugens. Compounds 3a, 3c, and 3e exhibited ≥90.3% activity at a dose of 500 mg/L. Moreover, some of the compounds showed promising antibacterial activities against Pseudomonas solanacearum. Compound 3a showed particularly potent antibacterial activity that reached 88.1% against tomato bacterial wilt at a dose of 200 mg/L.

Bottom Line: A synthetic route to obtain neonicotinoid analogs with dihydropyridine by the reaction of intermediates 2 (pyridyl (thiazolyl) methyl-2-substituted-methyl-ideneimidazolidine) and intermediates 1 (cyanoacrylates) and different aromatic aldehydes in acetonitrile under reflux conditions is presented.The effects of different solvents, bases, and reaction time on the reaction of 3a were investigated.The results of this study suggest that neonicotinoid analogs with dihydropyridine could cause N. lugens death and restrain P. solanacearum growth.

View Article: PubMed Central - HTML - PubMed

Affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang, China. basong@gzu.edu.

ABSTRACT

Background: Nilaparvata lugens, a major pest in rice-growing areas, is extremely difficult to manage. Neonicotinoids have increasingly been used in crop protection and animal health care against N. lugens. To discover new bioactive molecules and pesticides, we combined the active structure of cyanoacrylates, aromatic aldehydes, and substituted pyridyl (thiazolyl) methyl-2-substituted-methylidene-imidazolidine derivatives for the design and synthesis of a series of novel neonicotinoid analogs with dihydropyridine.

Results: A series of neonicotinoid analogs with dihydropyridine were synthesized. Their structures were characterized by IR, 1H NMR, 13C NMR, and elemental analysis and their insecticidal and antibacterial activities were assessed. Preliminary biological activity tests showed that all of the title compounds feature insecticidal activities against N. lugens at 500 mg/L. Moreover, some compounds showed promising antibacterial activities against Pseudomonas solanacearum (e.g., Tobacco bacterial wilt and Tomato bacterial wilt) at a dose of 200 mg/L.

Conclusion: A synthetic route to obtain neonicotinoid analogs with dihydropyridine by the reaction of intermediates 2 (pyridyl (thiazolyl) methyl-2-substituted-methyl-ideneimidazolidine) and intermediates 1 (cyanoacrylates) and different aromatic aldehydes in acetonitrile under reflux conditions is presented. The effects of different solvents, bases, and reaction time on the reaction of 3a were investigated. The results of this study suggest that neonicotinoid analogs with dihydropyridine could cause N. lugens death and restrain P. solanacearum growth.

No MeSH data available.


Related in: MedlinePlus