Insecticidal and Neuroblocking Activities of Acetamiprid and Related Compounds

Kiriyama, Kazuhisa; Itazu, Yuki; Kagabu, Shinzo; Nishimura, Keiichiro

doi:10.1584/jpestics.28.8

Cited by 26 publications

(23 citation statements)

References 21 publications

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“…With compound 2, the frequency decreased to zero around 13 min after the start of treatment at 1:3 Â 10 À6 M. With compound 18, however, some discharges were still counted even 20 min after the start of treatment at 5:7 Â 10 À4 M, this being the highest concentration tested. By estimating in a similar manner to that for the previous electrophysiological experiments, 21,22,[32][33][34] the blocking concentration for compounds 18, 26 and 27 was almost the same in a range of 0.6-1.0 mM. The much larger values than for prototype 2 of 4.5 mM are due to the evidently weak neuroblocking activity of these acetals.…”

Section: Resultssupporting

confidence: 64%

Prodrug-Oriented Molecular Design of Neonicotinoids: Preparation of Imidacloprid-Related 5,5-Dimethoxy-1,3-diazacyclohexane Derivatives and Their Insecticidal Activity

Kagabu

Hibi

Nishimura

2005

Bioscience, Biotechnology, and Biochemistry

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Prodrug-oriented molecular design was attempted for the potent acyclic neonicotinoid insecticide, clothianidin (1-(2-chloro-5-thiazolylmethyl)-3-methyl-2-nitroguanidine). Molecules bearing a CH 2 COCH 2 bridge linking the 1,3-NH ends of clothianidin or their acetals would possibly be hydrolyzed, regenerating the mother compounds. This strategy was used to prepare seven acetals of clothianidin-based molecules that combined 2-chloro-5-thiazolylmethyl, 6-chloro-3-pyridylmethyl or 3-tetrahydrofurfuryl with a nitroimine, cyanoimine or nitromethylene group. The key intermediate, 1,3-diamino-2,2-dimethoxypropane, was prepared from the dihydroxyacetone dimer in four steps. A selected acetal showed a characteristic nerve-impulse pattern for neonicotinoids on an excised American cockroach ganglion, although the neuroblocking activity was fairly low. Some acetals were highly insecticidal against the pea aphid at 0.8-20 ppm 7 days after a spray treatment, this being in a contrast to their far weaker activity by injection into American cockroaches. The biological results suggest that the intrinsic insecticidal activities of the acetals are weak, but would exhibit enhanced activity if hydrolyzed in an external environment.

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Section: Resultssupporting

confidence: 64%

Prodrug-Oriented Molecular Design of Neonicotinoids: Preparation of Imidacloprid-Related 5,5-Dimethoxy-1,3-diazacyclohexane Derivatives and Their Insecticidal Activity

Kagabu

Hibi

Nishimura

2005

Bioscience, Biotechnology, and Biochemistry

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“…We have thus far observed the activity enhancement of neonicotinoid compounds by the presence of PB and NIA. 1,8,14,16,17,[21][22][23]30,31) Also, in the present case, the potency improvement was observed in all compounds. The high synergistic effect for compound 23 was noticeable; the potency was enhanced by factor 2.…”

Section: )supporting

confidence: 74%

“…Interestingly, the derivatives of imidazolidine, oxazolidine and pyrrolidine (18,20,22) were apparently higher than the commercialized thiazolidine derivative (23) in activity. As for the appending heteroaromatic nucleus, the activity of the chloropyridyl residue was greater than the chlorothiazolyl, as in the nitro compounds.…”

Section: Insecticidal Potency and The Synergistic Effectmentioning

confidence: 88%

“…8,17,[21][22][23][24][25] In brief, a nerve preparation containing the abdominal fifth and sixth ganglia of a male adult American cockroach was excised and placed in a saline solution. One of two bundles of the nerve cord was taken up 60 S. Kagabu et al Journal of Pesticide Science Alone Ratio…”

Section: Neurophysiological Assaymentioning

confidence: 99%

“…19) In this respect, we can predict that the synergistic ratio will be larger for a compound with a larger electron density at the target site(s). The synergistic ratio order of 4, 1.7 and 1.1 among the derivatives of pyrrolidine (22), imidazolidine (18), oxazolidine (20), respectively, can be explained by the order of their Mulliken charge magnitudes on their C4s (Table 2) under the assumption that the metabolites of the pyrrolidine and the oxazolidine derivatives have similar activity tendency to the imidazolidine one. The obviously low synergistic ratio of 0.4 for nitromethylene-pyrrolidine (4) compared with 1.7 for cyanoimine derivative (22) despite having the almost same charge values was noted.…”

Section: )mentioning

confidence: 99%

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Insecticidal and neuroblocking potencies of variants of the thiazolidine moiety of thiacloprid and quantitative relationship study for the key neonicotinoid pharmacophore

Kagabu

Nishimura

Naruse

et al. 2008

Journal of Pesticide Science

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The pharmacophore of the neonicotinoid insecticide thiacloprid, cyanoiminothiazolidine, was modified to heterocycles such as imidazolidine, pyrrolidine and oxazolidine (the central ring hereafter). Their 6-chloro-3-pyridylmethyl or 5-chloro-3-thiazolylmethyl derivatives were examined for insecticidal activity against the American cockroach by injection and neuroblocking activity using the cockroach ganglion. The derivatives showed strong insecticidal activity with the minimum lethal dose (MLD) of about 10 nmol, which were however mostly weaker than the corresponding nitromethylene or nitroimine compounds. The activity was enhanced in the presence of synergists. The neuroblocking effect of cyanoimino compounds was at the micromolar level. Quantitative analysis for 23 variants of the key pharmacophore, constructed with the central ring conjugated to an NCN, CHNO 2 , or NNO 2 , showed that the neuroblocking potency is proportional to the Mulliken charge on the nitro oxygen atom or cyano nitrogen atom. The optimum log P value was evaluated as 1.19. The equation for the insecticidal-vs. the neuroblocking-potencies indicated that both potencies are related proportionally with each other when the other factors are the same.

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Nervous System

2007

Modern Crop Protection Compounds

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Insecticidal and Neuroblocking Activities of Acetamiprid and Related Compounds

Cited by 26 publications

References 21 publications

Prodrug-Oriented Molecular Design of Neonicotinoids: Preparation of Imidacloprid-Related 5,5-Dimethoxy-1,3-diazacyclohexane Derivatives and Their Insecticidal Activity

Prodrug-Oriented Molecular Design of Neonicotinoids: Preparation of Imidacloprid-Related 5,5-Dimethoxy-1,3-diazacyclohexane Derivatives and Their Insecticidal Activity

Insecticidal and neuroblocking potencies of variants of the thiazolidine moiety of thiacloprid and quantitative relationship study for the key neonicotinoid pharmacophore

Nervous System

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