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Fri Nov 15 02:06:22 EST 2002

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Search: acetamiprid


1

Biorational agents--mechanism and importance in IPM and IRM programs for controlling agricultural pests.

Full Author Name: Ishaaya, I; Kontsedalov, S; Mazirov, D; Horowitz, A R.

Ishaaya I, Kontsedalov S, Mazirov D, Horowitz AR.

Meded Rijksuniv Gent Fak Landbouwkd Toegep Biol Wet. 2001;66(2a):363-74.

[Article in English]


Department of Entomology, Agricultural Research Organization, Volcani Center, Bet Dagan 50250, Israel. vpisha@netvision.net.il

Among the new approaches for controlling agricultural pests is the development of novel compounds affecting specific processes in insects such as chitin synthesis inhibitors, juvenile hormone mimics and ecdysone agonists. In addition, efforts have been made to develop compounds acting selectively on groups of insects by inhibiting or enhancing biochemical sites such as respiration (diafenthiuron), the nicotinyl acetylcholine receptors (imidacloprid and acetamiprid), the GABA receptors (avermectins), the salivary glands of sucking pests (pymetrozine) and others. Among the most recent novel insecticides with selective properties are novaluron, thiamethoxam, emamectin and spinosad. Novaluron (Rimon) is a novel chitin synthesis inhibitor that acts by both ingestion and contact. It is a powerful suppressor of lepidopteran larvae such as Spodoptera littoralis and Helicoverpa armigera (by ingestion) and of whiteflies such as Bemisia tabaci and Trialeurodes vaporariorum (by contact). Thiamethoxam (Actarn), a novel neonicotinoid acts specifically on aphids and whiteflies. Emamectin (Proclaim), an avermectin derivative acts on GABA receptor affecting diversity of insects such as mites, lepidopterans and thrips. Spinosad (Tracer) seems to act on both acetylcholine and GABA receptors affecting diversity of insect species and is considered an important agent for controlling the western flower thrips.

Publication Types: 

  • Journal Article

ISSN: 1373-7503
NLM Unique ID: 100967625
Country: Belgium
Entry Date: 20021111
Entrez Date: 2002/11/12 4:0
MeSH Date: 2002/11/12 4:0
Citation Subset: IM
Publication Status: ppublish
Meded Rijksuniv Gent Fak Landbouwkd Toegep Biol Wet 2001;66(2a):363-74
MEDLINE Citation: NLM
PMID: 12425057 UI: 22312680 [PubMed - in process]
From PubMed

2

Toxicological and mechanistic studies on neonicotinoid cross resistance in Q-type Bemisia tabaci (Hemiptera: Aleyrodidae).

Full Author Name: Nauen, Ralf; Stumpf, Natascha; Elbert, Alfred.

Nauen R, Stumpf N, Elbert A.

Pest Manag Sci. 2002 Sep;58(9):868-75.

[Article in English]


Bayer AG, Agrochemicals Division, Building 6220, D-51368 Leverkusen, Germany. ralf.nauen@bayercropscience.com

The tobacco whitefly, Bemisia tabaci Gennadius (Homoptera: Aleyrodidae) is a serious pest in numerous cropping systems and has developed a high degree of resistance against several chemical classes of insecticides. One of the latest group of insecticides introduced to the market were the neonicotinoids (chloronicotinyls), acting agonistically on insect nicotinic acetylcholine receptors. Resistance to neonicotinoid insecticides has recently been shown to occur, especially in Q-type B tabaci in some places in Almeria, Spain, whereas control of B-type B tabaci in many other intense cropping systems worldwide has remained on high levels. Our study revealed that neonicotinoid-resistant Q-type strains from Almeria were often more than 100-fold less susceptible to thiamethoxam, acetamiprid and imidacloprid when tested in discontinuous systemic laboratory bioassays. The resistance factors were generally 2- to 3-fold lower in leaf-dip bioassays. In addition to the Spanish strains, we obtained two other highly neonicotinoid-cross-resistant B tabaci greenhouse populations, one from Italy (December 1999) and one from Germany (June 2001). A molecular diagnostic analysis revealed that both strains also belong to the (Spanish) subtype Q of the B tabaci species complex. The resistance levels of Q-type whitefly strains derived from Almeria greenhouses in 1999 remained stable for at least two years, even when maintained in the laboratory without any selection pressure. The biochemical mechanisms conferring resistance to neonicotinoids have not yet been elucidated in detail, but synergist studies suggested a possible involvement of microsomal monooxygenases. Furthermore, we checked two Almerian strains of B tabaci isolated in 1998 and 1999 and demonstrated that neonicotinoid resistance is not due to an altered [3H]imidacloprid binding site of nicotinic acetylcholine receptors.

Publication Types: 

  • Journal Article

ISSN: 1526-498X
NLM Unique ID: 100898744
Country: United States
Entry Date: 20020917
Entrez Date: 2002/9/18 10:0
MeSH Date: 2002/9/18 10:0
Citation Subset: IM
Publication Status: ppublish
Pest Manag Sci 2002 Sep;58(9):868-75
MEDLINE Citation: NLM
PMID: 12233176 UI: 22219478 [PubMed - in process]
From PubMed

3

Selective Toxicity of Neonicotinoids Attributable to Specificty of Insect and Mammalian Nicotinic Receptors.

Full Author Name: Tomizawa; Casida.

Tomizawa M, Casida JE.

Annu Rev Entomol. 2002 Aug 28;

[Article in English]


Selective Toxicity of Neonicotinoids Attributable to Specificty of Insect and Mammalian Nicotinic Receptors Motohiro Tomizawa (1) John E. Casida (2) (1) Department of Environmental Science, Policy Mana, University of California, Berkeley, Berkeley, CA 94720-3112 (2) Division of Insect Biology, University of California, Berkeley, Berkeley, CA 94720-3112 Author e-mail information: Motohiro Tomizawa - tomizawa@nature.berkeley.edu John E. Casida - ectl@nature.berkeley.edu Neonicotinoids, the most important new class of synthetic insecticides of the past three decades, are used to control sucking insects both on plants and on companion animals. Imidacloprid (the principal example), nitenpyram, acetamiprid, thiacloprid, thiamethoxam, and others act as agonists at the insect nicotinic acetylcholine receptor (nAChR). The botanical insecticide nicotine acts at the same target without the neonicotinoid level of effectiveness or safety. Fundamental differences between the nAChRs of insects and mammals confer remarkable selectivity for the neonicotinoids. Whereas ionized nicotine binds at an anionic subsite in the mammalian nAChR, the negatively tipped ("magic" nitro or cyano) neonicotinoids interact with a proposed unique subsite consisting of cationic amino acid residue(s) in the insect nAChR. Knowledge reviewed here of the functional architecture and molecular aspects of the insect and mammalian nAChRs and their neonicotinoid-binding site lays the foundation for continued development and use of this new class of safe and effective insecticides.

Publication Types: 

  • Journal Article

ISSN: 0066-4170
Journal Title Code: 6DN
NLM Unique ID: 0372367
Entry Date: 2002Sep4
Entrez Date: 2002/9/5 10:0
MeSH Date: 2002/9/5 10:0
http://ento.annualreviews.org/cgi/reprint/091801.112731
Article Identifier: 10.1146/annurev.ento.48.091801.112731 [doi], 091801.112731 [pii]
Publication Status: aheadofprint
Annu Rev Entomol 2002 Aug 28
MEDLINE Citation: NLM
PMID: 12208819 [PubMed - as supplied by publisher]
From PubMed

4

Determination of acetamiprid, imidacloprid, and nitenpyram residues in vegetables and fruits by high-performance liquid chromatography with diode-array detection.

Full Author Name: Obana, Hirotaka; Okihashi, Msahiro; Akutsu, Kazuhiko; Kitagawa, Yoko; Hori, Shinjiro.

Obana H, Okihashi M, Akutsu K, Kitagawa Y, Hori S.

J Agric Food Chem. 2002 Jul 31;50(16):4464-7.

[Article in English]


Osaka Prefectural Institute of Public Health, 1-3-69 Nakamichi, Higashinari, Osaka, 5370025 Japan. obana@iph.pref.osaka.jp

Determination of 3 neonicotinoid insecticides, nitenpyram, imidacloprid, and acetamiprid, was studied. Vegetables and fruits were extracted with acetonitrile. The crude extract was passed through a weak anion-exchange cartridge (PSA). The effluent was subjected to silica gel cartridge. Imidacloprid and acetamiprid were eluted with 10 mL of 4:6 (v/v) acetone/hexane, followed by nitenpyram with acetone (20 mL). Pesticides were determined by HPLC with a C-18 column and diode-array detection system. Imidacloprid and acetamiprid were recovered at about 90% at the spike levels with 0.2 and 2 mg/kg in cucumber, potato, tomato, eggplant, Japanese radish, and grape. Nitenpyram was recovered at 64-80%. Relative standard deviations were less than 10% throughout all the recovery tests. In the residue analysis, agriculturally incurred pesticides at 0.08-0.14 mg/kg were designated with UV spectra compared with respective reference standards.

Publication Types: 

  • Journal Article

MeSH Terms: 

  • Chromatography, High Pressure Liquid/*methods
  • Fruit/*chemistry
  • Imidazoles/analysis
  • Insecticides, Botanical/*analysis
  • Pesticide Residues/*analysis
  • Pyridines/analysis
  • Vegetables/*chemistry

Substances: 

  • 0 (Imidazoles)
  • 0 (Insecticides, Botanical)
  • 0 (Pesticide Residues)
  • 0 (Pyridines)
  • 0 (acetamiprid)
  • 0 (nitenpyram)
  • 105827-78-9 (imidacloprid)

ISSN: 0021-8561
NLM Unique ID: 0374755
Country: United States
Entry Date: 20020724
Date Completed: 20020911
Entrez Date: 2002/7/26 10:0
MeSH Date: 2002/9/12 10:1
Citation Subset: IM
http://dx.doi.org/10.1021/jf025539q
Article Identifier: jf025539q [pii]
Publication Status: ppublish
J Agric Food Chem 2002 Jul 31;50(16):4464-7
MEDLINE Citation: NLM
PMID: 12137461 UI: 22133379 [PubMed - indexed for MEDLINE]
From PubMed

5

Translocation and translaminar bioavailability of two neonicotinoid insecticides after foliar application to cabbage and cotton.

Full Author Name: Buchholz, Anke; Nauen, Ralf.

Buchholz A, Nauen R.

Pest Manag Sci. 2002 Jan;58(1):10-6.

[Article in English]


Bayer AG, Crop Protection, Research Insecticides, D-51368 Leverkusen, Germany.

A laboratory study was undertaken to investigate the leaf systemic properties and the translaminar aphicidal activity of two commercialised neonicotinoid (chloronicotinyl) insecticides. For that purpose [14C]imidacloprid was subjected to uptake and translocation studies in cabbage and cotton after foliar application. Foliar penetration and short-term translocation patterns of imidacloprid were similar in both plant species. Nevertheless imidacloprid penetrated twice as much into cabbage leaves as it did into cotton leaves. It showed a comparable translaminar behaviour and was entirely translocated acropetally, indicating its well-known xylem mobility. The translaminar and acropetal movement of imidacloprid and acetamiprid were quantified by simple laboratory bioassays using the green peach aphid, Myzus persicae (Sulzer), and the cotton aphid, Aphis gossypii (Glover), as typical homopteran pests for cabbage and cotton, respectively. A single dose (7.5 micrograms AI per leaf) applied to the upper leaf surface of cabbage and cotton was tested against aphids feeding on the lower leaf surface both close to and distant from the site of application 1, 5 and 12 days after treatment. The translaminar residual activity of imidacloprid on cabbage leaves was superior to that of acetamiprid, whereas its translaminar efficacy against A gossypii on cotton was inferior to that of acetamiprid. However, oral ingestion bioassays using an artificial double membrane feeding system revealed no significant differences in intrinsic activity between the two neonicotinoids tested.

Publication Types: 

  • Journal Article

MeSH Terms: 

  • Anabasine/chemistry
  • Animal
  • Aphids/*drug effects
  • Biological Transport
  • Brassica/*metabolism/parasitology
  • Carbon Radioisotopes
  • Cotton/*metabolism/parasitology
  • Imidazoles/administration & dosage/chemistry/*metabolism
  • Insecticides, Botanical/administration & dosage/chemistry/*metabolism
  • Plant Leaves/*metabolism/parasitology
  • Pyridines/chemistry/*metabolism

Substances: 

  • 0 (Carbon Radioisotopes)
  • 0 (Imidazoles)
  • 0 (Insecticides, Botanical)
  • 0 (Pyridines)
  • 0 (acetamiprid)
  • 105827-78-9 (imidacloprid)
  • 494-52-0 (Anabasine)

ISSN: 1526-498X
NLM Unique ID: 100898744
Country: United States
Entry Date: 20020212
Date Completed: 20020829
Entrez Date: 2002/2/13 10:0
MeSH Date: 2002/8/30 10:1
Citation Subset: IM
Publication Status: ppublish
Pest Manag Sci 2002 Jan;58(1):10-6
MEDLINE Citation: NLM
PMID: 11838278 UI: 21827976 [PubMed - indexed for MEDLINE]
From PubMed

6

Effect of selected insecticides on Homalodisca coagulata (Homoptera: Cicadellidae) and transmission of oleander leaf scorch in a greenhouse study.

Full Author Name: Bethke, J A; Blua, M J; Redak, R A.

Bethke JA, Blua MJ, Redak RA.

J Econ Entomol. 2001 Oct;94(5):1031-6.

[Article in English]


Department of Entomology, University of California, Riverside 92521, USA. bethke@citrus.ucr.edu

Homalodisca coagulata (Say) is a recent introduction to California. It is known to spread a strain of the bacterium Xylella fastidiosa Wells, Raju, Hung, Weisberg, Mandelco-Paul & Brenner that induces oleander leaf scorch disease in oleander, Nerium oleander L. Oleander leaf scorch is lethal to oleander and threatens to decimate one of the most important landscape shrubs in California. Towards developing a management strategy for H. coagulata-spread oleander leaf scorch, we documented the affects of selected insecticides on H. coagulata mortality, feeding behavior, and disease transmission in a greenhouse study. Oleanders treated with fenpropathrin, fenpropathrin + acephate, and imidacloprid caused significant mortality to caged H. coagulata within 4 h of exposure. Within 24 h, these pesticides caused nearly 100% mortality 3 wk after treatment. In other experiments, acetamiprid and fenpropathrin treatments reduced time spent feeding and total time on plants. H. coagulata on fenpropathrin-, acetamiprid-, and imidacloprid-treated oleander died in less than 13 min on average. Oleander leaf scorch transmission by H. coagulata was blocked by applications of foliar-applied acetamiprid, and soil-applied imidacloprid and thiamethoxam.

Publication Types: 

  • Journal Article

MeSH Terms: 

  • Animal
  • *Hemiptera/physiology
  • Insect Control/*methods
  • *Insect Vectors/physiology
  • *Insecticides
  • Plant Diseases/microbiology
  • Support, Non-U.S. Gov't
  • gamma Proteobacteria

Substances: 

  • 0 (Insecticides)

ISSN: 0022-0493
NLM Unique ID: 2985127R
Country: United States
Entry Date: 20011029
Date Completed: 20020103
Entrez Date: 2001/10/30 10:0
MeSH Date: 2002/1/5 10:1
Citation Subset: IM
Publication Status: ppublish
J Econ Entomol 2001 Oct;94(5):1031-6
MEDLINE Citation: NLM
PMID: 11681662 UI: 21537751 [PubMed - indexed for MEDLINE]
From PubMed

7

Insect nicotinic acetylcholine receptor: conserved neonicotinoid specificity of [(3)H]imidacloprid binding site.

Full Author Name: Zhang, A; Kayser, H; Maienfisch, P; Casida, J E.

Zhang A, Kayser H, Maienfisch P, Casida JE.

J Neurochem. 2000 Sep;75(3):1294-303.

[Article in English]


Environmental Chemistry and Toxicology Laboratory, Department of Environmental Science, Policy, and Management, University of California, Berkeley 94720-3112, USA.

The insect nicotinic acetylcholine receptor (nAChR) is a major target for insecticide action. The rapidly expanding use of neonicotinoid insecticides of varied structures makes it increasingly important to define similarities and differences in their action, particularly for the first-generation chloropyridinyl compounds versus the second-generation chlorothiazolyl derivatives. We have shown with Musca domestica that a convenient and relevant determination of the neonicotinoid insecticide target is a binding site assay with [(3)H]imidacloprid ([(3)H]IMI). This study uses membranes from the aphids MYZUS: persicae and Aphis craccivora and from heads of the flies DROSOPHILA: melanogaster and Musca domestica to characterize the [(3)H]IMI binding sites relative to their number and possible species variation in structure-activity relationships. With emphasis on commercial neonicotinoids, six potent chloropyridinyl compounds are compared with the corresponding six chlorothiazolyl analogues (syntheses are given for chemicals prepared differently than previously described). The preference for chloropyridinyl versus chlorothiazolyl is not dependent on the insect species examined but instead on other structural features of the molecule. The chlorothiazolyl substituent generally confers higher potency in the clothianidin and desmethylthiamethoxam series and the chloropyridinyl moiety in the imidacloprid, thiacloprid, acetamiprid, and nitenpyram series. Two chlorothiazolyl compounds compete directly with the chloropyridinyl [(3)H]IMI for the same binding sites in MYZUS: and DROSOPHILA: membranes. This study shows conserved neonicotinoid specificity of the [(3)H]IMI binding site in each of the four insect species examined.

Publication Types: 

  • Journal Article

MeSH Terms: 

  • Amino Acid Sequence
  • Animal
  • Aphids
  • Binding Sites
  • Cell Membrane/metabolism
  • Conserved Sequence
  • Drosophila
  • *Houseflies
  • Imidazoles/chemical synthesis/chemistry/*pharmacokinetics
  • Insecticides/*pharmacokinetics
  • Insects
  • Kinetics
  • Receptors, Nicotinic/*chemistry/*metabolism
  • Species Specificity
  • Structure-Activity Relationship
  • Support, U.S. Gov't, P.H.S.
  • Tritium

Substances: 

  • 0 (Imidazoles)
  • 0 (Insecticides)
  • 0 (Receptors, Nicotinic)
  • 10028-17-8 (Tritium)
  • 105827-78-9 (imidacloprid)

Grant Support: 

  • R01 ES08424/ES/NIEHS

ISSN: 0022-3042
NLM Unique ID: 2985190R
Country: United States
Entry Date: 20000912
Date Completed: 20000912
Date Revised: 20001218
Entrez Date: 2000/8/11 11:0
MeSH Date: 2000/9/19 11:1
Citation Subset: IM
http://www.jneurochem.org/cgi/pmidlookup?view=full&pmid=10936213
http://www.blackwell-synergy.com/rd.asp?abbrev=J%20Neurochem&vol=75&page=1294&goto=abstract
Publication Status: ppublish
J Neurochem 2000 Sep;75(3):1294-303
MEDLINE Citation: NLM
PMID: 10936213 UI: 20396206 [PubMed - indexed for MEDLINE]
From PubMed

8

Characterization of nicotinic acetylcholine receptors from the insects Aphis craccivora, Myzus persicae, and Locusta migratoria by radioligand binding assays: relation to thiamethoxam action.

Full Author Name: Wiesner, P; Kayser, H.

Wiesner P, Kayser H.

J Biochem Mol Toxicol. 2000;14(4):221-30.

[Article in English]


Novartis Crop Protection AG, Research Biochemistry, Basel, Switzerland.

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 > or = 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]-alpha-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.

Publication Types: 

  • Journal Article

MeSH Terms: 

  • Animal
  • Bungarotoxins/metabolism
  • Imidazoles/metabolism
  • Insecticides/*pharmacology
  • Insects/*metabolism
  • Nicotine/metabolism
  • Radioligand Assay
  • Receptors, Nicotinic/*metabolism
  • Species Specificity
  • Tritium

Substances: 

  • 0 (Bungarotoxins)
  • 0 (Imidazoles)
  • 0 (Insecticides)
  • 0 (Receptors, Nicotinic)
  • 10028-17-8 (Tritium)
  • 105827-78-9 (imidacloprid)
  • 54-11-5 (Nicotine)

ISSN: 1095-6670
NLM Unique ID: 9717231
Country: United States
Entry Date: 20000621
Date Completed: 20000621
Date Revised: 20001218
Entrez Date: 2000/5/2 9:0
MeSH Date: 2000/6/24 11:0
Citation Subset: IM
http://dx.doi.org/10.1002/(SICI)1099-0461(2000)14:4<221::AID-JBT7>3.0.CO;2-6
Article Identifier: 10.1002/(SICI)1099-0461(2000)14:4<221::AID-JBT7>3.0.CO;2-6 [pii]
Publication Status: ppublish
J Biochem Mol Toxicol 2000;14(4):221-30
MEDLINE Citation: NLM
PMID: 10789501 UI: 20248363 [PubMed - indexed for MEDLINE]
From PubMed

9

Minor structural changes in nicotinoid insecticides confer differential subtype selectivity for mammalian nicotinic acetylcholine receptors.

Full Author Name: Tomizawa, M; Casida, J E.

Tomizawa M, Casida JE.

Br J Pharmacol. 1999 May;127(1):115-22.

[Article in English]


Department of Environmental Science, Policy and Management, University of California, Berkeley 94720-3112, USA.

The major nitroimine insecticide imidacloprid (IMI) and the nicotinic analgesics epibatidine and ABT-594 contain the 6-chloro-3-pyridinyl moiety important for high activity and/or selectivity. ABT-594 has considerable nicotinic acetylcholine receptor (AChR) subtype specificity which might carry over to the chloropyridinyl insecticides. This study considers nine IMI analogues for selectivity in binding to immuno-isolated alpha1, alpha3 and alpha7 containing nicotinic AChRs and to purported alpha4beta2 nicotinic AChRs. Alpha1- and alpha3-containing nicotinic AChRs (both immuno-isolated by mAb 35, from Torpedo and human neuroblastoma SH-SY5Y cells, respectively) are between two and four times more sensitive to DN-IMI than to (-)-nicotine. With immuno-isolated alpha3 nicotinic AChRs, the tetrahydropyrimidine analogues of IMI with imine or nitromethylene substituents are 3-4 fold less active than (-)-nicotine. The structure-activity profile with alpha3 nicotinic AChRs from binding assays is faithfully reproduced in agonist potency as induction of 86rubidium ion efflux in intact cells. Alpha7-containing nicotinic AChRs of SH-SY5Y cells (immuno-isolated by mAb 306) and rat brain membranes show maximum sensitivity to the tetrahydropyrimidine analogue of IMI with the nitromethylene substituent. The purported alpha4beta2 nicotinic AChRs [mouse (Chao & Casida, 1997) and rat brain] are similar in sensitivity to DN-IMI, the tetrahydropyrimidine nitromethylene and nicotine. The commercial insecticides (IMI, acetamiprid and nitenpyram) have low to moderate potency at the alpha3 and purported alpha4beta2 nicotinic AChRs and are essentially inactive at alpha1 and alpha7 nicotinic AChRs. In conclusion, the toxicity of the analogues and metabolites of nicotinoid insecticides in mammals may involve action at multiple receptor subtypes with selectivity conferred by minor structural changes.

Publication Types: 

  • Journal Article

MeSH Terms: 

  • Animal
  • Antibodies, Monoclonal/pharmacology
  • Cholinergic Agents/chemistry/*pharmacology/toxicity
  • Electric Organ/drug effects/metabolism
  • Human
  • Imidazoles/chemistry/*pharmacology/toxicity
  • Insecticides/chemistry/*pharmacology/toxicity
  • Mice
  • Nicotine/pharmacology
  • Nicotinic Agonists/pharmacology
  • Radioligand Assay
  • Rats
  • Receptors, Nicotinic/*drug effects
  • Rubidium Radioisotopes/diagnostic use
  • Structure-Activity Relationship
  • Support, U.S. Gov't, P.H.S.
  • Torpedo
  • Tumor Cells, Cultured

Substances: 

  • 0 (Antibodies, Monoclonal)
  • 0 (Cholinergic Agents)
  • 0 (Imidazoles)
  • 0 (Insecticides)
  • 0 (Nicotinic Agonists)
  • 0 (Receptors, Nicotinic)
  • 0 (Rubidium Radioisotopes)
  • 105827-78-9 (imidacloprid)
  • 54-11-5 (Nicotine)

Grant Support: 

  • P01 ES00049/ES/NIEHS
  • R01 ES08424/ES/NIEHS

ISSN: 0007-1188
NLM Unique ID: 7502536
Country: England
Entry Date: 19990901
Date Completed: 19990901
Date Revised: 20001218
Entrez Date: 1999/6/16
MeSH Date: 1999/6/16 0:1
Citation Subset: IM
http://www.brjpharmacol.org/cgi/pmidlookup?view=full&pmid=10369463
Publication Status: ppublish
Br J Pharmacol 1999 May;127(1):115-22
MEDLINE Citation: NLM
PMID: 10369463 UI: 99296154 [PubMed - indexed for MEDLINE]
From PubMed

10

[125I]Azidonicotinoid photoaffinity labeling of insecticide-binding subunit of Drosophila nicotinic acetylcholine receptor.

Full Author Name: Tomizawa, M; Casida, J E.

Tomizawa M, Casida JE.

Neurosci Lett. 1997 Nov 21;237(2-3):61-4.

[Article in English]


Department of Environmental Science, Policy and Management, University of California, Berkeley 94720-3112, USA.

The novel synthetic nicotinoid insecticide imidacloprid is a high affinity ligand for the insect nicotinic acetylcholine receptor (nAChR). The goal of this study is to identify the ligand- and insecticide-binding subunit of Drosophila nAChR with a novel [125I]azidonicotinoid ([125I]AN) photoaffinity probe modeled on imidacloprid. [125I]AN photoaffinity labels a single polypeptide in Drosophila head membranes corresponding in molecular mass to 66 kDa at a specific site inhibited by various cholinergic ligands including (-)-nicotine, cytisine, carbachol, alpha-bungarotoxin and d-tubocurarine as well as the insecticides imidacloprid and acetamiprid, pharmacologically consistent with the ligand- and insecticide-binding subunit. The Drosophila nAChR, isolated with three putative subunits (69, 66 and 61 kDa) using a nicotinoid-agarose affinity column, is labeled by [125I]AN primarily at the 66 kDa subunit and secondarily at the 61 kDa subunit. Clearly, the novel synthetic nicotinoid insecticides are valuable contributors in exploring the structure and function of the Drosophila nAChR.

Publication Types: 

  • Journal Article

MeSH Terms: 

  • Animal
  • Brain/metabolism
  • Drosophila
  • Imidazoles/pharmacology
  • In Vitro
  • Insecticides/*metabolism
  • Membranes/metabolism
  • Photoaffinity Labels
  • Rats
  • Receptors, Nicotinic/*metabolism
  • Support, U.S. Gov't, P.H.S.

Substances: 

  • 0 (Imidazoles)
  • 0 (Insecticides)
  • 0 (Photoaffinity Labels)
  • 0 (Receptors, Nicotinic)
  • 105827-78-9 (imidacloprid)

Grant Support: 

  • P01 ES00049/ES/NIEHS

ISSN: 0304-3940
NLM Unique ID: 7600130
Country: Ireland
Entry Date: 19980305
Date Completed: 19980305
Date Revised: 20001218
Entrez Date: 1998/2/7
MeSH Date: 1998/2/7 0:1
Citation Subset: IM
Publication Status: ppublish
Neurosci Lett 1997 Nov 21;237(2-3):61-4
MEDLINE Citation: NLM
PMID: 9453215 UI: 98113960 [PubMed - indexed for MEDLINE]
From PubMed

11

Whitefly (Hemiptera: Aleyrodidae) binding site for imidacloprid and related insecticides: a putative nicotinic acetylcholine receptor.

Full Author Name: Chao, S L; Dennehy, T J; Casida, J E.

Chao SL, Dennehy TJ, Casida JE.

J Econ Entomol. 1997 Aug;90(4):879-82.

[Article in English]


Department of Environmental Science, Policy, and Management, University of California, Berkeley 94720-3112, USA.

Imidacloprid is used extensively to control sweetpotato whiteflies, Bemisia argentifolii Bellows & Perring [also known as B. tabaci (Gennadius) biotype B]. As a radioligand, [3H]imidacloprid binds rapidly to a single class of high-affinity sites in membrane preparations from whole adult whiteflies with an apparent dissociation constant of 2 nM and maximal binding capacity of 101 fmol/mg protein. Three related compounds (the nitromethylene analog of imidacloprid, acetamiprid, and nitenpyram) inhibit [3H]imidacloprid binding by 50% at 0.40, 2.9, and 57 nM, respectively. The pharmacological profile of the binding site (examined with imidacloprid and the analogs listed above, and nicotine, alpha-bungarotoxin, carbachol, acetylcholine [with paraoxon], and atropine) is consistent with that anticipated for a nicotinic acetylcholine receptor and correlates well with binding results for house fly, Musca domestica L., head membranes under the same conditions. Thus, [3H]imidacloprid is a suitable radioligand to investigate the putative nicotinic acetylcholine receptor of Bemisia and the possible modifications of this target site associated with selection of resistant strains.

Publication Types: 

  • Journal Article

MeSH Terms: 

  • Animal
  • Binding Sites
  • Hemiptera
  • Imidazoles/chemistry/*metabolism
  • Insecticides/chemistry/*metabolism
  • Insects/*metabolism
  • Kinetics
  • Molecular Structure
  • Receptors, Nicotinic/*metabolism
  • Support, U.S. Gov't, P.H.S.

Substances: 

  • 0 (Imidazoles)
  • 0 (Insecticides)
  • 0 (Receptors, Nicotinic)
  • 105827-78-9 (imidacloprid)

Grant Support: 

  • PO1 ES00049/ES/NIEHS

ISSN: 0022-0493
NLM Unique ID: 2985127R
Country: United States
Entry Date: 19970912
Date Completed: 19970912
Date Revised: 20001218
Entrez Date: 1997/8/1
MeSH Date: 1997/8/1 0:1
Citation Subset: IM
Publication Status: ppublish
J Econ Entomol 1997 Aug;90(4):879-82
MEDLINE Citation: NLM
PMID: 9260539 UI: 97407297 [PubMed - indexed for MEDLINE]
From PubMed

 

The following information was generated from the

Toxicology Literature Online Databank (TOXLINE),

a database of the National Library of Medicine's TOXNET system

(http://toxnet.nlm.nih.gov) on November 15, 2002.

Query: The word acetamiprid (All Fields).

Singular and plural forms were searched.

 

A NOVEL INSECTICIDE ACETAMIPRID

YAMADA Y

214TH AMERICAN CHEMICAL SOCIETY NATIONAL MEETING, LAS VEGAS, NEVADA, USA,

SEPTEMBER 7-11, 1997. ABSTRACTS OF PAPERS AMERICAN CHEMICAL SOCIETY; 214 (1-2).

1997. AGRO 17. [BIOSIS]

Method to determination of total residues of the insecticide acetamiprid and its

metabolites in crops by gas chromatography.

TOKIEDA M; OZAWA M; KOBAYASHI S; GOMYO T

JOURNAL OF PESTICIDE SCIENCE; 22 (2). 1997. 77-83. [BIOSIS]

RESIDUE DETERMINATION METHOD FOR THE INSECTICIDE ACETAMIPRID IN CROPS BY GAS

CHROMATOGRAPHY

TOKIEDA M; IIYOSHI K; SUGIOKA K; GOMYO T

JOURNAL OF PESTICIDE SCIENCE; 22 (2). 1997. 129-132. [BIOSIS]

MOSPILAN ACETAMIPRID NI-25. A NEW SYSTEMIC INSECTICIDE

MATSUDA M; TAKAHASHI H

AGROCHEMICALS JAPAN; 0 (68). 1996. 20-21. [BIOSIS]

NEONICOTINOIDS MODE OF ACTION AND SELECTIVITY

YAMAMOTO I

AGROCHEMICALS JAPAN; 0 (68). 1996. 14-15. [BIOSIS]

Method to determination of total residues of the insecticide acetamiprid and its metabolites in crops by gas chromatography.

Authors:

TOKIEDA M

OZAWA M

KOBAYASHI S

GOMYO T

Author Address: Analysis Chemicals Pesticide Residue, Nisso Chemical Analysis Serv. Co. Ltd., Takada, Odawara 250-02, Japan.

Source: JOURNAL OF PESTICIDE SCIENCE; 22 (2). 1997. 77-83.

Abstract:

BIOSIS COPYRIGHT: BIOL ABS. An analytical method has been developed for the determination of acetamiprid, (E)-N1-((6-chloro-3-pyridyl)methyl)-N2-cyano-N1-methylacetamidine (ATP) and its metabolites, IM-2-1, IM-0, IC-0 and IM-0-Glucose in crops by gas chromatography (GC). ATP and its metabolites in crops were extracted with methanol and derivatized to methyl 6-chloronicotinate (IC-0-Me) through alkali hydrolysis, potassium permanganate oxidation and then esterification by diazomethane, followed by column chromatography clean-up and GC determination. The limit of detection was 0.01 ppm and the recoveries of fortified samples ranged from 74 to 92%.

Medical Subject Headings (MeSH):

BIOCHEMISTRY/METHODS

HERBICIDES

PEST CONTROL

PESTICIDES

ARACHNIDA

ENTOMOLOGY/ECONOMICS

INSECTICIDES

PEST CONTROL

PESTICIDES

Keywords:

Biochemical Methods-General

Pest Control

Economic Entomology-Chemical and Physical Control

CAS Registry Numbers:

160430-64-8

160430-64-8

21543-49-7

5326-23-8

Language: English

Coden:

RESIDUE DETERMINATION METHOD FOR THE INSECTICIDE ACETAMIPRID IN CROPS BY GAS CHROMATOGRAPHY

Authors:

TOKIEDA M

IIYOSHI K

SUGIOKA K

GOMYO T

Source: JOURNAL OF PESTICIDE SCIENCE; 22 (2). 1997. 129-132.

Abstract:

BIOSIS COPYRIGHT: BIOL ABS. RRM RESEARCH ARTICLE PEST MANAGEMENT RESIDUE DETERMINATION ACETAMIPRID INSECTICIDE GAS CHROMATOGRAPHY ANALYTICAL METHOD

Medical Subject Headings (MeSH):

BIOCHEMISTRY/METHODS

HERBICIDES

PEST CONTROL

PESTICIDES

ARACHNIDA

ENTOMOLOGY/ECONOMICS

INSECTICIDES

PEST CONTROL

PESTICIDES

Keywords:

Biochemical Methods-General

Pest Control

Economic Entomology-Chemical and Physical Control

Language: English

Coden:

NNGAD

Entry Month: August, 1997

Year of Publication: 1997

Secondary Source ID: BIOSIS/97/18798

MOSPILAN ACETAMIPRID NI-25. A NEW SYSTEMIC INSECTICIDE

Authors:

MATSUDA M

TAKAHASHI H

Source: AGROCHEMICALS JAPAN; 0 (68). 1996. 20-21.

Abstract:

BIOSIS COPYRIGHT: BIOL ABS. RRM RESEARCH ARTICLE TEA TOBACCO FRUIT TREES VEGETABLES HEMIPTERA THYSANOPTERA LEPIDOPTERA COLEOPTERA ISOPTERA PEST HOST PEST MANAGEMENT ACETAMIPRID NI-25 SYSTEMIC INSECTICIDE MOSPILAN BIOLOGICAL CHARACTERISTICS FORMULATION MODE OF ACTION ECONOMIC ENTOMOLOGY HORTICULTURE AGRONOMY

Medical Subject Headings (MeSH):

BIOCHEMISTRY

SOIL

TOBACCO/GROWTH & DEVELOPMENT

VEGETABLES

PLANTS/GROWTH & DEVELOPMENT

HERBICIDES

PEST CONTROL

PESTICIDES

ARACHNIDA

ENTOMOLOGY/ECONOMICS

PLANTS

ARACHNIDA

ENTOMOLOGY/ECONOMICS

FRUIT

NUTS

ARACHNIDA

ENTOMOLOGY/ECONOMICS

INSECTICIDES

PEST CONTROL

PESTICIDES

ANIMAL

DISEASE

INSECTS/PARASITOLOGY

PLANTS

PLANTS

PLANTS

COLEOPTERA

HEMIPTERA

INSECTS

LEPIDOPTERA

INSECTS

Keywords:

Biochemical Studies-General

Agronomy-Tobacco Crops

Horticulture-Vegetables

Horticulture-General

Pest Control

Economic Entomology-Field

Economic Entomology-Fruits and Nuts

Economic Entomology-Chemical and Physical Control

Invertebrata

Angiospermae

Solanaceae

Theaceae

Coleoptera

Hemiptera

Isoptera

Lepidoptera

Thysanoptera

Language: English

Coden:

AGJAE

Entry Month: June, 1997

NEONICOTINOIDS MODE OF ACTION AND SELECTIVITY

Authors:

YAMAMOTO I

Source: AGROCHEMICALS JAPAN; 0 (68). 1996. 14-15.

Abstract:

BIOSIS COPYRIGHT: BIOL ABS. RRM JOURNAL ARTICLE PEST MANAGEMENT NEONICOTINOID INSECTICIDE IMIDACLOPRID NTN-33893 CONFIDOR GAUCHO ADMIRE NITENPYRAM TI-304 BESTGUARD ACETAMIPRID NI-25 MOSPILAN PESTICIDES MODE OF ACTION SELECTIVITY SAFETY

Medical Subject Headings (MeSH):

BIOCHEMISTRY

BIOPHYSICS

MACROMOLECULAR SYSTEMS

MOLECULAR BIOLOGY

POISONING

ANIMALS, LABORATORY

HERBICIDES

PEST CONTROL

PESTICIDES

ARACHNIDA

ENTOMOLOGY/ECONOMICS

INSECTICIDES

PEST CONTROL

PESTICIDES

Keywords:

Biochemical Studies-General

Biophysics-Molecular Properties and Macromolecules

Toxicology-General

Pest Control

Economic Entomology-Chemical and Physical Control

CAS Registry Numbers:

160430-64-8

160430-64-8

150824-47-8

105827-78-9

54-11-5

Language: English

Coden:

AGJAE

Entry Month: June, 1997

Year of Publication: 1996

Secondary Source ID: BIOSIS/97/07420