Relationship between Insecticidal and Nerve-Excitatory Activities of Imidacloprid and Its Alkylated Congeners at the Imidazolidine NH Site

Nishimura, Keiichiro; Tanaka, Masahiro; Iwaya, Kazuko; Kagabu, Shinzo

doi:10.1006/pest.1998.2384

Cited by 37 publications

(57 citation statements)

References 18 publications

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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: 73%

“…Yield (propargyl propyl benzenephosphonate; NIA) was the same sample used in our previous studies. 8,[14][15][16][17] NIA was originally an inhibitor of the hydrolytic metabolism of pyrethroids, 18) and was found to be a synergist for neonicotinoids in insecticidal tests. 14) Recently, Nishiwaki et al evidenced the interference of the enzymatic hydroxylation at the imidazolidine ring of imidacloprid by NIA.…”

Section: -(2-chloropyridin-5-ylmethyl)-2-(cyanoimino)-oxazolidinementioning

confidence: 99%

“…8,[14][15][16][17] Various volumes (1-10 ml) of each compound dissolved in methanol containing some amount of dimethyl sulfoxide (DMSO) were injected into the abdomen of a cockroach. Organic solvents alone in this range did not have a toxic effect.…”

Section: Insecticidal Test Against American Cockroachesmentioning

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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Section: )supporting

confidence: 73%

Section: -(2-chloropyridin-5-ylmethyl)-2-(cyanoimino)-oxazolidinementioning

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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“…an increase in impulse frequencies immediately after the treatment followed by a drop to a level lower than the control. 4,[14][15][16][17] The concentration needed to block of nerve impulses (BC) was 100 mM. This was much larger than the corresponding concentration of compound 1, a tethered bis-imidacloprid (Table 1).…”

Section: Resultsmentioning

confidence: 97%

“…4,[14][15][16][17] Various volumes (1-10 ml) of each compound dissolved in dimethyl sulfoxide (DMSO) containing some amount of methanol were injected into the abdomen. Organic solvents alone in this range did not have any toxic effect.…”

Section: Insecticidal Testmentioning

confidence: 99%

1,6-Bis[1-(2-chloro-5-thiazolylmethyl)-2-nitroiminoimidazolidin-3-yl]hexane and 1,3,5-tris[1-(6-chloronicotinyl)-2-nitroiminoimidazolidin-3-ylmethyl]benzene-Synthesis and insecticidal and neuroblocking activities in American cockroaches, Periplaneta americana

2006

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A chlorothiazole-based hexamethylene divalent neonicotinoid and trivalent 1,3,5-tris[1-(6-chloronicotinyl)-2-nitroiminoimidazolidin-3-ylmethyl]benzene were synthesized, and tested for the insecticidal activity using American cockroaches by injection without (alone) and with synergists, piperonyl butoxide and propargyl propyl benzenephosphonate. The minimal lethal dose (MLD) in mol was 8.9 for the divalent compound alone, which was 4 times larger than that of the corresponding chloropyridylbased dimer. The MLD was 34 nmol for the trivalent compound, somewhat larger than for the divalent 1,3-xylenyl analog (20 nmol). The synergists combined enhanced their effectiveness about 8-20 times. Neurophysiological measurements were conducted using a nerve preparation containing the abdominal fifth and sixth ganglia of an American cockroach. The trivalent compound showed a pattern characteristic of neonicotinoids and its neuroblocking potency was 100 mM.

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Characterization of nicotinic acetylcholine receptors from the insectsAphis craccivora,Myzus persicae, andLocusta migratoria by radioligand binding assays: Relation to thiamethoxam action

Wiesner

Kayser

2000

J. Biochem. Mol. Toxicol.

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Thiamethoxam, a new neonicotinoid insecticide acting at nicotinic acetylcholine receptors, was characterized in competition binding assays with [3‐H]‐imidacloprid, a specific nicotinic ligand, using membranes from the aphids Aphis craccivora and Myzus persicae, and from the locust Locusta migratoria. In all insects, Scatchard analysis suggested two binding sites for imidacloprid with Kd values in the range of 1 nM and 10 nM, respectively. The Hill values were significantly below 1 (range of 0.63 to 0.85). In contrast to imidacloprid and nicotine, the potency of thiamethoxam to displace [3‐H]‐imidacloprid varied considerably among these insects. Thiamethoxam was more active than nicotine on Aphis receptors but 100‐fold less in Locusta, a nontarget insect. Comparable relations were found to nithiazine. In Myzus, the inhibition curve for thiamethoxam was shallow. This suggested a heterogeneous receptor population displaying a range of binding affinities to thiamethoxam in this aphid. In all three insects, the other neonicotinoid insecticides studied competed with [3‐H]‐imidacloprid in the same order: thiacloprid > imidacloprid ≥ acetamiprid > nitenpyram. N‐Methylation of imidacloprid strongly reduced the affinity to the imidacloprid site, whereas N‐demethylation of thiamethoxam resulted in a comparable increase of affinity. Supplementary assays were performed with (−)‐[3‐H]‐nicotine and [3‐H]‐α‐bungarotoxin on locust membranes. Overall, the data suggested that the outstanding insecticidal properties of thiamethoxam may be due to either a different binding site on nicotinic receptors, or receptor isoforms, or specific pharmakokinetic behavior, rather than to exceptional affinity to one of the examined binding sites. © 2000 John Wiley & Sons, Inc. J Biochem Toxicol 14:221–230, 2000

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Relationship between Insecticidal and Nerve-Excitatory Activities of Imidacloprid and Its Alkylated Congeners at the Imidazolidine NH Site

Cited by 37 publications

References 18 publications

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

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

1,6-Bis[1-(2-chloro-5-thiazolylmethyl)-2-nitroiminoimidazolidin-3-yl]hexane and 1,3,5-tris[1-(6-chloronicotinyl)-2-nitroiminoimidazolidin-3-ylmethyl]benzene-Synthesis and insecticidal and neuroblocking activities in American cockroaches, Periplaneta americana

Characterization of nicotinic acetylcholine receptors from the insectsAphis craccivora,Myzus persicae, andLocusta migratoria by radioligand binding assays: Relation to thiamethoxam action

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