Insecticidal and Neuroblocking Potencies of Variants of the Imidazolidine Moiety of Imidacloprid-Related Neonicotinoids and the Relationship to Partition Coefficient and Charge Density on the Pharmacophore

Kagabu, Shinzo; Ishihara, R; Hieda, Yosuke; Nishimura, Keiichiro; Naruse, Yuji

doi:10.1021/jf0623440

Cited by 58 publications

(60 citation statements)

References 42 publications

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“…Interestingly, the activity strongly depends on the tether length, and the hexamethylene derivative (34) was the highest. The minimal lethal dose of as low as 2.2 nmol is comparable to 2.5 nmol of imidacloprid (1).…”

Section: )mentioning

confidence: 89%

Pharmacophore of neonicotinoid insecticides

Kagabu

2008

J. Pestic. Sci.

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Our recent study related to neonicotinoid pharmacophore was presented. The first topic described on the QSAR study with 17 variants of 2-nitroiminoimizolidine. The insect neuroblocking potency is proportionally related both to the Mulliken charge on the nitro oxygen atom and log P. The second raised the functional possibility of the 3-fluoropropyl group as an H-bond acceptor for the neonicotinoid skeleton. Its 2-nitroiminoimidazolidine derivative actually showed the insecticidal tendency common to the neonicotinoids bearing a 6-chloro-3-pyridylmethyl group, although the activating strength was not as high as expected. The third introduced a new type of neonicotinoid compounds of alkylene-tethered twin-structure. The insecticidal activity against American cockroaches was dependent on the tether length and maximized at the hexamethylene with the minimum lethal dose of 2.2 nmol/insects, comparable to that of imidacloprid.

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Section: )mentioning

confidence: 89%

Pharmacophore of neonicotinoid insecticides

Kagabu

2008

J. Pestic. Sci.

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“…8) Here either, we cannot calculate any significant stereoelectronic differences between these inversely dihalogenated derivatives, considering the equivalent potency against green rice leafhoppers of 6-chloronicotinyl-nitromethyleneimidazolidine and 6-fluoro derivative. 9) One of the remarkable features of neonicotinoids is their excellent activity against sucking insects, 3) and it is undeniable that the notable systemicity shown by the log P value of 0.53 of imidacloprid 6) contributes to insecticidal prominence. The measured log P values for the positional isomers, 2 and 3a, were 0.79 and 0.98 at 25°C, respectively, which indicates that the 6-chloro-5-fluoro derivative (2) is apparently more hydrophilic than the isomer (3a).…”

Section: Insecticidal Activitymentioning

confidence: 99%

Preparation of 5-chloro-6-fluoroimidacloprid analogs and comparison of their insecticidal activity in a laboratory test with a 6-chloro-5-fluoro analog

2007

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Five new neonicotinoid compounds bearing a 5-chloro-6-fluoronicotinyl group were prepared and their insecticidal activity against brown rice planthopper, green peach aphid and common cutworm under laboratory conditions was compared with 1-(6-chloro-5-fluoronicotinyl)-2-nitroiminoimidazolidine. 5-Fluoroimidacloprid controlled the two hemipteras at 0.2 ppm at the same dose level of imidacloprid, while the positional isomers showed far lower activity. None of the tested compounds controlled the lepidoptera at 200 ppm.

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“…4) Since the first product, imidacloprid (IMI), was discovered, a number of molecular modifications have been attempted of the neonicotinoid insecticide class to find potential effectors. [5][6][7][8][9][10] New chemical entities seem to be designed based on the binding model referring to the existing products; consequently, most are compliant with the Lipinski rule. Recently, we devised a unique neonicotinoid structure of alkylene-tethered twin neonicotinoids and reported their biological properties.…”

Section: Introductionmentioning

confidence: 99%

Unexpected plant-systemic insecticidal properties of alkylene-tethered bis-imidacloprid derivatives

et al. 2010

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Alkylene-tethered bis-imidacloprid (bis-IMI) derivatives were evaluated for insecticidal activity after foliar dipping, foliar spraying and under systemic conditions. Insecticidal activity on the dipped leaves was dependent on the tether length, and heptamethylene (C7) and octamethylene (C8) derivatives, their best compounds, almost completely controlled the green peach aphid (Myzus persicae) at 10 mg l Ϫ1, while all divalent compounds were weak against the tobacco cutworm (Spodoptera litura). C6 and C7 derivatives were examined for residual and systemic activity. Complete control of the green peach aphid by both compounds was observed on evaluation 72 hr after insect release on the eleventh day after foliar treatment, and the C7 derivative showed distinguished systemic activity against the brown plant hopper (N. Lugens) and the green peach aphid. The bis-IMIs should be disqualified as insecticidal candidates on virtual screening criteria owing to its high log P value, large molecular mass and excessive numbers of hydrogen-bond acceptors and rotatable bonds. Additional criteria may be necessary to account for the plant-mobile insecticidal behavior of such novel structures as bis-IMIs.

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Insecticidal and Neuroblocking Potencies of Variants of the Imidazolidine Moiety of Imidacloprid-Related Neonicotinoids and the Relationship to Partition Coefficient and Charge Density on the Pharmacophore

Cited by 58 publications

References 42 publications

Pharmacophore of neonicotinoid insecticides

Pharmacophore of neonicotinoid insecticides

Preparation of 5-chloro-6-fluoroimidacloprid analogs and comparison of their insecticidal activity in a laboratory test with a 6-chloro-5-fluoro analog

Unexpected plant-systemic insecticidal properties of alkylene-tethered bis-imidacloprid derivatives

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