3-(6-Chloronicotinyl)-2-nitromethylene-thiazolidine as a New Class of Insecticide Acting against Lepidoptera Species

Shiokawa, Kohzoh; Moriya, Keiichi; Shibuya, Katsuhiko; Hattori, Yoshikazu; Tsuboi, Sadao; Kagabu, Shinzo

doi:10.1271/bbb.56.1364

Cited by 24 publications

(15 citation statements)

References 1 publication

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“…increased hydrophobicity may lead to an improved penetration through cuticle. The S analog of 6-Cl-PMNI was claimed to have an excellent activity on lepidopteran pests (Shiokawa et al, 1992). Acetamiprid, although binding is inferior to others, was far higher in hydrophobicity (log P 0.80) than imidacloprid (0.59) and nitenpyram (-0.64) and was effective on lepidopteran pests (Matsuda and Takahashi, 1996).…”

Section: Hydrophobicity Is An Important Factor Contributing To Insectmentioning

confidence: 99%

Structural factors contributing to insecticidal and selective actions of neonicotinoids

Yamamoto

Tomizawa

Saito

et al. 1998

Arch. Insect Biochem. Physiol.

132

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Nicotinoids and neonicotinoids are characterized by the presence of the 3‐pyridylmethylamine moiety in their structure. In the former, the amino nitrogen atom is ionized, while in the latter the corresponding nitrogen atom is not ionized but bears a partial positive charge. Both types of insecticides interact with nicotinic acetylcholine receptor (nAChR) of insect origin. The poor interaction of neonicotinoids with vertebrate nAChR was shown by its poor binding affinity to the nAChR from Torpedo electric organ and rat brain and poor activation with nAChR expressed in Xenopus oocytes. The full positive charge was essential to interact with the vertebrate nAChR, while the 3‐pyridylmethylamine moiety with a partial positive charge was enough to interact with the insect nAChR. For penetration into the insect central nervous system, hydrophobicity seemed to play an important role, as indicated by the binding of the injected compounds to the housefly head nAChR. The ionization reduced hydrophobicity and limited the penetration of nicotinoids, resulting in less insecticidal activity. Among neonicotinoids, nitromethylene type compounds, though far higher in binding affinity, were less hydrophobic than the corresponding nitroimine type, and the net result was better or inferior insecticidal activity. A chlorine atom at the 6 position of the 3‐pyridyl group found in commercialized neonicotinoids contributes to increased binding affinity and more importantly hydrophobicity, thus increasing insecticidal activity. N‐Me‐imidacloprid was found to be a propesticide of imidacloprid. Arch. Insect Biochem. Physiol. 37:24–32, 1998. © 1998 Wiley‐Liss, Inc.

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Section: Hydrophobicity Is An Important Factor Contributing To Insectmentioning

confidence: 99%

Structural factors contributing to insecticidal and selective actions of neonicotinoids

Yamamoto

Tomizawa

Saito

et al. 1998

Arch. Insect Biochem. Physiol.

132

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“…Neonicotinoids such as those shown in Figure 1 are relatively new insecticides structurally related each other, and are originated from imidacloprid, which has been put on the market since 1992 [1–3]. Neonicotinoid insecticides are similar to nicotinoids in binding to the nicotinic acetylcholine receptor of insects [4,5].…”

Section: Introductionmentioning

confidence: 99%

Development of Immunoassay Based on Monoclonal Antibody Reacted with the Neonicotinoid Insecticides Clothianidin and Dinotefuran

Uchigashima

Watanabe

Ito

et al. 2012

Sensors

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Enzyme-linked immunosorbent assay (ELISA) based on a monoclonal antibody (MoAb) was developed for the neonicotinoid insecticide clothianidin. A new clothianidin hapten (3-[5-(3-methyl-2-nitroguanidinomethyl)-1,3-thiazol-2-ylthio] propionic acid) was synthesized and conjugated to keyhole limpet hemocyanin, and was used for monoclonal antibody preparation. The resulting MoAb CTN-16A3-13 was characterized by a direct competitive ELISA (dc-ELISA). The 50% of inhibition concentration value with clothianidin was 4.4 ng/mL, and the working range was 1.5–15 ng/mL. The antibody showed high cross-reactivity (64%) to dinotefuran among the structurally related neonicotinoid insecticides. The recovery examinations of clothianidin for cucumber, tomato and apple showed highly agreement with the spiked concentrations; the recovery rate was between 104% and 124% and the coefficient of variation value was between 1.8% and 15%. Although the recovery rate of the dc-ELISA was slightly higher than that of HPLC analysis, the difference was small enough to accept the dc-ELISA as a useful method for residue analysis of clothianidin in garden crops.

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“…Imidacloprid, 1‐(6‐chloro‐3‐pyridylmethyl)‐N‐nitroimidazolidin‐2‐ylideneamine (Figure 1), was the result of further structural developments of the prototype nitromethylenes (Kagabu et al , 1992; Shiokawa et al , 1992; Moriya et al , 1993). It is a potent insecticide, active on a variety of insect species, is selectively toxic to insects over vertebrates (Moriya et al , 1993) and has a higher potency for insect over vertebrate nicotinic AChRs (Zwart et al , 1994).…”

Section: Introductionmentioning

confidence: 99%

Effects of the α subunit on imidacloprid sensitivity of recombinant nicotinic acetylcholine receptors

Matsuda

Buckingham

Freeman

et al. 1998

British J Pharmacology

125

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1 Imidacloprid is a new insecticide with selective toxicity for insects over vertebrates. Recombinant (a4b2) chicken neuronal nicotinic acetylcholine receptors (AChRs) and a hybrid nicotinic AChR formed by co-expression of a Drosophila melanogaster neuronal a subunit (SAD) with the chicken b2 subunit were heterologously expressed in Xenopus oocytes by nuclear injection of cDNAs. The agonist actions of imidacloprid and other nicotinic AChR ligands ((+)-epibatidine, (7)-nicotine and acetylcholine) were compared on both recombinant nicotinic AChRs by use of two-electrode, voltage-clamp electrophysiology. 2 Imidacloprid alone of the 4 agonists behaved as a partial agonist on the a4b2 receptor; (+)-epibatidine, (7)-nicotine and acetylcholine were all full, or near full, agonists. Imidacloprid was also a partial agonist of the hybrid Drosophila SAD chicken b2 receptor, as was (7)-nicotine, whereas (+)-epibatidine and acetylcholine were full agonists. 3 The EC 50 of imidacloprid was decreased by replacing the chicken a4 subunit with the Drosophila SAD a subunit. This a subunit substitution also resulted in an increase in the EC 50 for (+)-epibatidine, (7)-nicotine and acetylcholine. Thus, the Drosophila (SAD) a subunit contributes to the greater apparent anity of imidacloprid for recombinant insect/vertebrate nicotinic AChRs. 4 Imidacloprid acted as a weak antagonist of ACh-mediated responses mediated by SADb2 hybrid receptors and as a weak potentiator of ACh responses mediated by a4b2 receptors. This suggests that imidacloprid has complex eects upon these recombinant receptors, determined at least in part by the a subunit.

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3-(6-Chloronicotinyl)-2-nitromethylene-thiazolidine as a New Class of Insecticide Acting against Lepidoptera Species

Abstract: 1-(6-Chloronicotinyl)-2-nitroimino-imidazolidine (common name: imidacloprid) and related imidazolidine compounds control effectively hemiptera and other sucking insects. 1) However their activity level against lepidoptera species is not high enough for practical use. 2) Imidazolidines

Cited by 24 publications

References 1 publication

Structural factors contributing to insecticidal and selective actions of neonicotinoids

Structural factors contributing to insecticidal and selective actions of neonicotinoids

Development of Immunoassay Based on Monoclonal Antibody Reacted with the Neonicotinoid Insecticides Clothianidin and Dinotefuran

Effects of the α subunit on imidacloprid sensitivity of recombinant nicotinic acetylcholine receptors

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