1-Diazinylmethyl-2-nitromethylene- and 2-Nitroimino-imidazolidines as New Potential Insecticides

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

doi:10.1584/jpestics.18.119

Cited by 21 publications

(11 citation statements)

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“…Stability of cotmpoun`ts 6, 21, 23, and 32 uncler hydbolytic conditions ( Degraclation by simulated sunlight (Table V) The photolysis experiment was carried out in a mixed solvent of acetonitrile and water because of the insuMcient 7 solubility of some compounds in water alone, A notable general phenomenon for photolysis was that the nitromethylene derivatives decomposed more rapidly than the nitroimine and cyanoimine partners. A pertinent example is that chloronicotinyl-2-nitromethyleneimidazolidine (6) decomposed by 57% with 1.5h of irradiation, while the halfilife period fbr imidacloprid (21) was 3,Oh and cyanoimine (23) decayed by only 2% in 24h. Oxazolidine (16), thiazolidine (17), and pyrrolidine (18), which bear a nitremethylene group, decomposed mostly within an hour.…”

Section: 25mentioning

confidence: 99%

“…t".si:1$tSclged,eLc?X,"?･fis,2d,;,h,e, However, the listed intrinsic activity expressed by binding 1690; NMR j. (90MHz, DMSO-d,), 3.22 (4H, br, s), 4.25 (2H, s), 6.45 aMnity or Ki values, the minimum concentration in "M to (2H, s), 7･46 (IH, d, J==8,1 Hz), 7,70 (IH, dd, J==8.1 and 2,4Hz), 8.27 31:d.gOtt,? (l,Al,O,"&Y,bt2ehtsfi2d.,"; f6'kgi{f,-'c?N`,"oZ'cfg"i the concentration in ppm to kill 909t6 of the green rice preparationqf22.AsolutionofN-(6-chloro-3-pyridyl)rnethy]ethyleneleathopper in greenhouse tests (Table I).…”

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confidence: 99%

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Stability Comparison of Imidacloprid and Related Compounds under Simulated Sunlight, Hydrolysis Conditions, and to Oxygen

Kagabu

Medej

1995

Bioscience, Biotechnology, and Biochemistry

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Lipophilicity and the tendency for decomposition of imidac}oprid and related compounds by oxygen, hydrolytic mediums, and simulated sunlight were studied to see whether these physicochemical faetors haye any relation to the biological actiyity of the compounds in vitro, in a greenhouse, or under field conditions. Lipophi]icity indices based on HPLC bore no definite relationship with the binding aMnity to the acetylcholine receptor. Howeyer, the compounds haying high insecticidal potential in greenhouse tests were generally less hydrophilic. In neutral water or in an oxygen-saturated solution, the compounds tested were completely stable.Aneyidentdifferencewasobseryedintheirbehayiortowardthesunlightwayelength,thenitromethylene compounds decomposing far more rapidly than nitroimines like imidacloprid. The photolability of the nitromethylenes is ascribed to their longer maximum absorption wayelength of oyer 320nm. Imidacloprid(21),1-(6-chloronicotinyl)-2-nitroiminoimidespecially connected with the in vivo behavior of the azolidine, is a new insecticide with high activity especially molecules. However, we have not dealt here with the against sucking pests.2) The cliscovery of this compound behavior in soil, another important degradation pathway was the result of seeking improved activity by changing the for pesticides. structure of the originally announced insecticide, 2nitromethylenetetrahydrothiazine (SKI-71; 33).3) We have Materials and Methods prepared about 2000 compounds and selected imidacloprid Matexiais. The reagents and solvents used were of ttnalyticul grade. The for commercial use based on, above all, its insecticidal following compounds were prepared aocording to the descriptions in the gg`.

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Section: 25mentioning

confidence: 99%

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confidence: 99%

Stability Comparison of Imidacloprid and Related Compounds under Simulated Sunlight, Hydrolysis Conditions, and to Oxygen

Kagabu

Medej

1995

Bioscience, Biotechnology, and Biochemistry

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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). Bai et al (1991) found that imidacloprid depolarizes an identified cockroach motor neurone and displaces [ 125 I]‐α‐bungarotoxin binding to cockroach nerve cord preparations, establishing its action on native, α‐bungarotoxin‐sensitive insect nicotinic AChRs.…”

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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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“…In the present study, our focus was on the deprotonated 6‐hydroxynicotinic acid (6OHNic) ion. The hydroxynicotinic acids (2‐, 4‐, 5‐ and 6‐hydroxy) are widely used in the manufacture of industrial products, and 6OHNic is an important precursor to many modern insecticides. At a more fundamental level, the hydroxypyridines are important model systems for study of the tautomerization of N‐heterocyclic compounds.…”

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Infrared multiple‐photon dissociation spectroscopy of deprotonated 6‐hydroxynicotinic acid

Stipdonk

Kullman²,

Berden

2014

Rapid Comm Mass Spectrometry

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1-Diazinylmethyl-2-nitromethylene- and 2-Nitroimino-imidazolidines as New Potential Insecticides

Cited by 21 publications

References 2 publications

Stability Comparison of Imidacloprid and Related Compounds under Simulated Sunlight, Hydrolysis Conditions, and to Oxygen

Stability Comparison of Imidacloprid and Related Compounds under Simulated Sunlight, Hydrolysis Conditions, and to Oxygen

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

Infrared multiple‐photon dissociation spectroscopy of deprotonated 6‐hydroxynicotinic acid

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