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1
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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: 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 |
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2
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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: 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 |
|
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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: 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 |
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|
4
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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: 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: 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: MeSH
Terms: - Animal
- *Hemiptera/physiology
- Insect Control/*methods
- *Insect
Vectors/physiology
- *Insecticides
- Plant Diseases/microbiology
- Support,
Non-U.S. Gov't
- gamma
Proteobacteria
Substances: 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: 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: 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: 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: 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 |
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10
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[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: 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: 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 |
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11
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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: 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: 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]