|
Insecticidal activity against Aphis craccivora (cowpea aphid) assessed as mortality at 15.625 ug/mL measured after 1 day
|
Aphis craccivora
|
60.0
%
|
|
Journal : J Agric Food Chem
Year : 2007
Volume : 55
Issue : 1
First Page : 143
Last Page : 147
|
Insecticidal activity against Aphis craccivora (cowpea aphid) assessed as mortality at 62.5 ug/mL measured after 1 day
|
Aphis craccivora
|
94.0
%
|
|
Journal : J Agric Food Chem
Year : 2007
Volume : 55
Issue : 1
First Page : 143
Last Page : 147
|
Hydrophobicity, log P of the compound in octanol-water by shaking-flask method
|
None
|
-0.18
|
|
Journal : J Agric Food Chem
Year : 2007
Volume : 55
Issue : 3
First Page : 812
Last Page : 818
|
Toxic effect in Periplaneta americana (American cockroach) assessed as paralyzed insects after 24 hr of abdomen compound injection by insecticidal assay
|
Periplaneta americana
|
9.19
|
|
Journal : J Agric Food Chem
Year : 2007
Volume : 55
Issue : 3
First Page : 812
Last Page : 818
|
Neuroblocking activity in Periplaneta americana (American cockroach) nicotinic acetylcholine receptor in abdominal fifth and sixth ganglia nerve assessed as neuroblocking concentration by neurophysiological test
|
Periplaneta americana
|
5.02
|
|
Journal : J Agric Food Chem
Year : 2007
Volume : 55
Issue : 3
First Page : 812
Last Page : 818
|
Insecticidal activity against Nephotettix cincticeps (green rice leafhopper) assessed as mortality measured after 4 days
|
Nephotettix cincticeps
|
0.32
ppm
|
|
Journal : J Agric Food Chem
Year : 2011
Volume : 59
Issue : 7
First Page : 2887
Last Page : 2896
|
Photolysis of the compound assessed as half life at 30 degC by 250 W sun lamp
|
None
|
1.0
hr
|
|
Journal : J Agric Food Chem
Year : 2011
Volume : 59
Issue : 7
First Page : 2887
Last Page : 2896
|
Hydrophobicity, log P of the compound in octanol-water by shaking-flask method
|
None
|
-0.18
|
|
Journal : J Agric Food Chem
Title : Importance of physicochemical properties for the design of new pesticides.
Year : 2011
Volume : 59
Issue : 7
First Page : 2909
Last Page : 2917
Authors : Akamatsu M.
Abstract : The physicochemical properties of candidate compounds play important roles in the design of new pesticides. Pesticides must be absorbed by pests, be transported to the target site, and then interact with proteins. Hydrophobicity is very important for these processes. Log P, where P is the partition coefficient in the 1-octanol/water system, is commonly used as a hydrophobic descriptor and correlates with membrane permeation and transport. It was recently reported that permeability by the parallel artificial membrane permeation assay (PAMPA) could be used to predict human oral absorption of passively transported compounds. PAMPA, which is a rapid high-throughput screening system, may be useful to predict pesticide absorption because PAMPA permeability can be calculated using log P and other parameters. Electronic and structural properties as well as hydrophobicity are important factors for protein-ligand interaction. To show the importance of physicochemical properties, the classic QSAR and CoMFA of neonicotinoids and prediction of bioavailability of pesticides in terms of membrane permeability in comparison with drugs are described.
|
Toxic effect in Periplaneta americana (American cockroach) assessed as paralyzed insects after 24 hr of abdomen compound injection by insecticidal assay
|
Periplaneta americana
|
10.19
|
|
Journal : J Agric Food Chem
Title : Importance of physicochemical properties for the design of new pesticides.
Year : 2011
Volume : 59
Issue : 7
First Page : 2909
Last Page : 2917
Authors : Akamatsu M.
Abstract : The physicochemical properties of candidate compounds play important roles in the design of new pesticides. Pesticides must be absorbed by pests, be transported to the target site, and then interact with proteins. Hydrophobicity is very important for these processes. Log P, where P is the partition coefficient in the 1-octanol/water system, is commonly used as a hydrophobic descriptor and correlates with membrane permeation and transport. It was recently reported that permeability by the parallel artificial membrane permeation assay (PAMPA) could be used to predict human oral absorption of passively transported compounds. PAMPA, which is a rapid high-throughput screening system, may be useful to predict pesticide absorption because PAMPA permeability can be calculated using log P and other parameters. Electronic and structural properties as well as hydrophobicity are important factors for protein-ligand interaction. To show the importance of physicochemical properties, the classic QSAR and CoMFA of neonicotinoids and prediction of bioavailability of pesticides in terms of membrane permeability in comparison with drugs are described.
|
Neuroblocking activity in Periplaneta americana (American cockroach) nicotinic acetylcholine receptor in abdominal fifth and sixth ganglia nerve assessed as neuroblocking concentration by neurophysiological test
|
Periplaneta americana
|
5.02
|
|
Journal : J Agric Food Chem
Title : Importance of physicochemical properties for the design of new pesticides.
Year : 2011
Volume : 59
Issue : 7
First Page : 2909
Last Page : 2917
Authors : Akamatsu M.
Abstract : The physicochemical properties of candidate compounds play important roles in the design of new pesticides. Pesticides must be absorbed by pests, be transported to the target site, and then interact with proteins. Hydrophobicity is very important for these processes. Log P, where P is the partition coefficient in the 1-octanol/water system, is commonly used as a hydrophobic descriptor and correlates with membrane permeation and transport. It was recently reported that permeability by the parallel artificial membrane permeation assay (PAMPA) could be used to predict human oral absorption of passively transported compounds. PAMPA, which is a rapid high-throughput screening system, may be useful to predict pesticide absorption because PAMPA permeability can be calculated using log P and other parameters. Electronic and structural properties as well as hydrophobicity are important factors for protein-ligand interaction. To show the importance of physicochemical properties, the classic QSAR and CoMFA of neonicotinoids and prediction of bioavailability of pesticides in terms of membrane permeability in comparison with drugs are described.
|
Binding affinity to freshwater snail Lymnaea stagnalis AChBP assessed as [3H]EPI binding by radioligand binding assay
|
Lymnaea stagnalis
|
80.0
nM
|
|
Journal : J Agric Food Chem
Title : Unique neonicotinoid binding conformations conferring selective receptor interactions.
Year : 2011
Volume : 59
Issue : 7
First Page : 2825
Last Page : 2828
Authors : Tomizawa M, Casida JE.
Abstract : Neonicotinoid agonists selectively act on the insect nicotinic acetylcholine receptor (nAChR). The molecular basis for this specificity is deciphered by comparisons of two acetylcholine binding proteins (AChBPs) with distinct pharmacological profiles that serve as structural homologues for the nAChR subtypes. Aplysia AChBP has high neonicotinoid sensitivity, whereas Lymnaea AChBP has low neonicotinoid sensitivity, pharmacologies reminiscent of insect and vertebrate nAChR subtypes, respectively. The ligand-receptor interactions for these AChBPs were established by chemical and structural neurobiology approaches. Neonicotinoids and nicotinoids bind in a single conformation with Aplysia AChBP, wherein the electronegative nitro or cyano pharmacophore of the neonicotinoid faces in a reversed orientation relative to the cationic nicotinoid functionality. For Lymnaea AChBP, the neonicotinoids have two binding conformations in this vertebrate receptor model, which are completely inverted relative to each other, whereas nicotinoids are nestled in only one conserved conformation. Therefore, the unique binding conformations of nicotinic agonists determine the selective receptor interactions.
|
Binding affinity to salt water mollusc Aplysia californica AChBP Y55W mutant assessed as [3H]acetamiprid binding by radioligand binding assay
|
Aplysia californica
|
1.7
nM
|
|
Journal : J Agric Food Chem
Title : Unique neonicotinoid binding conformations conferring selective receptor interactions.
Year : 2011
Volume : 59
Issue : 7
First Page : 2825
Last Page : 2828
Authors : Tomizawa M, Casida JE.
Abstract : Neonicotinoid agonists selectively act on the insect nicotinic acetylcholine receptor (nAChR). The molecular basis for this specificity is deciphered by comparisons of two acetylcholine binding proteins (AChBPs) with distinct pharmacological profiles that serve as structural homologues for the nAChR subtypes. Aplysia AChBP has high neonicotinoid sensitivity, whereas Lymnaea AChBP has low neonicotinoid sensitivity, pharmacologies reminiscent of insect and vertebrate nAChR subtypes, respectively. The ligand-receptor interactions for these AChBPs were established by chemical and structural neurobiology approaches. Neonicotinoids and nicotinoids bind in a single conformation with Aplysia AChBP, wherein the electronegative nitro or cyano pharmacophore of the neonicotinoid faces in a reversed orientation relative to the cationic nicotinoid functionality. For Lymnaea AChBP, the neonicotinoids have two binding conformations in this vertebrate receptor model, which are completely inverted relative to each other, whereas nicotinoids are nestled in only one conserved conformation. Therefore, the unique binding conformations of nicotinic agonists determine the selective receptor interactions.
|
Binding affinity to recombinant Gallus gallus (chicken) alpha4beta2 nicotinic acetylcholine receptor assessed as [3H]NIC binding by radioligand binding assay
|
Gallus gallus
|
60.0
nM
|
|
Journal : J Agric Food Chem
Title : Unique neonicotinoid binding conformations conferring selective receptor interactions.
Year : 2011
Volume : 59
Issue : 7
First Page : 2825
Last Page : 2828
Authors : Tomizawa M, Casida JE.
Abstract : Neonicotinoid agonists selectively act on the insect nicotinic acetylcholine receptor (nAChR). The molecular basis for this specificity is deciphered by comparisons of two acetylcholine binding proteins (AChBPs) with distinct pharmacological profiles that serve as structural homologues for the nAChR subtypes. Aplysia AChBP has high neonicotinoid sensitivity, whereas Lymnaea AChBP has low neonicotinoid sensitivity, pharmacologies reminiscent of insect and vertebrate nAChR subtypes, respectively. The ligand-receptor interactions for these AChBPs were established by chemical and structural neurobiology approaches. Neonicotinoids and nicotinoids bind in a single conformation with Aplysia AChBP, wherein the electronegative nitro or cyano pharmacophore of the neonicotinoid faces in a reversed orientation relative to the cationic nicotinoid functionality. For Lymnaea AChBP, the neonicotinoids have two binding conformations in this vertebrate receptor model, which are completely inverted relative to each other, whereas nicotinoids are nestled in only one conserved conformation. Therefore, the unique binding conformations of nicotinic agonists determine the selective receptor interactions.
|
Binding affinity to Drosophila brain nicotinic acetylcholine receptor assessed as [3H]IMI binding by radioligand binding assay
|
Drosophila
|
0.12
nM
|
|
Journal : J Agric Food Chem
Title : Unique neonicotinoid binding conformations conferring selective receptor interactions.
Year : 2011
Volume : 59
Issue : 7
First Page : 2825
Last Page : 2828
Authors : Tomizawa M, Casida JE.
Abstract : Neonicotinoid agonists selectively act on the insect nicotinic acetylcholine receptor (nAChR). The molecular basis for this specificity is deciphered by comparisons of two acetylcholine binding proteins (AChBPs) with distinct pharmacological profiles that serve as structural homologues for the nAChR subtypes. Aplysia AChBP has high neonicotinoid sensitivity, whereas Lymnaea AChBP has low neonicotinoid sensitivity, pharmacologies reminiscent of insect and vertebrate nAChR subtypes, respectively. The ligand-receptor interactions for these AChBPs were established by chemical and structural neurobiology approaches. Neonicotinoids and nicotinoids bind in a single conformation with Aplysia AChBP, wherein the electronegative nitro or cyano pharmacophore of the neonicotinoid faces in a reversed orientation relative to the cationic nicotinoid functionality. For Lymnaea AChBP, the neonicotinoids have two binding conformations in this vertebrate receptor model, which are completely inverted relative to each other, whereas nicotinoids are nestled in only one conserved conformation. Therefore, the unique binding conformations of nicotinic agonists determine the selective receptor interactions.
|
Insecticidal activity against Cnaphalocrocis medinalis measured 5 days after artificial infestation
|
Cnaphalocrocis medinalis
|
200.0
ppm
|
|
Journal : Biosci. Biotechnol. Biochem.
Year : 1992
Volume : 56
Issue : 8
First Page : 1364
Last Page : 1365
|
Insecticidal activity against Plutella xylostella (diamondback moth) measured 5 days after artificial infestation
|
Plutella xylostella
|
40.0
ppm
|
|
Journal : Biosci. Biotechnol. Biochem.
Year : 1992
Volume : 56
Issue : 8
First Page : 1364
Last Page : 1365
|
Insecticidal activity against Nephotettix cincticeps (green rice leafhopper) measured 5 days after artificial infestation
|
Nephotettix cincticeps
|
0.32
ppm
|
|
Journal : Biosci. Biotechnol. Biochem.
Year : 1992
Volume : 56
Issue : 8
First Page : 1364
Last Page : 1365
|
Insecticidal activity against Spodoptera litura measured 5 days after artificial infestation
|
Spodoptera litura
|
8.0
ppm
|
|
Journal : Biosci. Biotechnol. Biochem.
Year : 1992
Volume : 56
Issue : 8
First Page : 1364
Last Page : 1365
|
Insecticidal activity against Nephotettix cincticeps (green rice leafhopper) measured after 5 days
|
Nephotettix cincticeps
|
0.32
ppm
|
|
Journal : Biosci. Biotechnol. Biochem.
Year : 1992
Volume : 56
Issue : 2
First Page : 362
Last Page : 363
|
Insecticidal activity against Nephotettix cincticeps (green rice leafhopper) infested on rice leaf assessed as mortality after 5 days
|
Nephotettix cincticeps
|
0.32
ppm
|
|
Journal : Biosci. Biotechnol. Biochem.
Year : 1992
Volume : 56
Issue : 2
First Page : 364
Last Page : 365
|
Insecticidal activity against Nephotettix cincticeps (green rice leafhopper) in compound treated germinated rice seedlings assessed as mortality measured after 5 days
|
Nephotettix cincticeps
|
0.32
ppm
|
|
Journal : Biosci. Biotechnol. Biochem.
Year : 1993
Volume : 57
Issue : 1
First Page : 127
Last Page : 128
|
Displacement of [3H]alpha-bungarotoxin from nicotinic acetylcholine receptor in Apis mellifera (honey bee) head membrane
|
Apis mellifera
|
110.0
nM
|
|
Journal : J Pesticide Sci
Year : 2000
Volume : 25
Issue : 1
First Page : 37
Last Page : 39
|
Acute toxicity in po dosed Mus musculus ICR (mouse) assessed as mortality measured after 14 days
|
Mus musculus
|
30.0
mg.kg-1
|
|
Journal : J Pesticide Sci
Year : 2000
Volume : 25
Issue : 1
First Page : 37
Last Page : 39
|
Insecticidal activity against adult Laodelphax striatella (small brown planthopper) at 0.0005 ug topically applied measured after 24 hr
|
Laodelphax striatella
|
100.0
%
|
|
Journal : J Pesticide Sci
Year : 2000
Volume : 25
Issue : 1
First Page : 37
Last Page : 39
|
Insecticidal activity against adult Laodelphax striatella (small brown planthopper) at 0.0005 ug topically applied measured after 3 hr
|
Laodelphax striatella
|
70.0
%
|
|
Journal : J Pesticide Sci
Year : 2000
Volume : 25
Issue : 1
First Page : 37
Last Page : 39
|
Insecticidal activity against larvae of Myzus persicae (green peach aphid) infested eggplant petiole treated with compound solution measured after 5 days
|
Myzus persicae
|
0.09
ppm
|
|
Journal : J Pesticide Sci
Year : 2000
Volume : 25
Issue : 1
First Page : 37
Last Page : 39
|
Insecticidal activity against larvae of Laodelphax striatella (small brown planthopper) fed with compound solution dipped rice seedling measured after 5 days by test tube method
|
Laodelphax striatella
|
0.3
ppm
|
|
Journal : J Pesticide Sci
Year : 2000
Volume : 25
Issue : 1
First Page : 37
Last Page : 39
|
Lipophilicity, log P of the compound
|
None
|
-0.18
|
|
Journal : J Pesticide Sci
Year : 2008
Volume : 33
Issue : 1
First Page : 9
Last Page : 13
|
Neuroblocking potency in Periplaneta americana (American cockroach) central nerve cord
|
Periplaneta americana
|
5.02
|
|
Journal : J Pesticide Sci
Year : 2008
Volume : 33
Issue : 1
First Page : 9
Last Page : 13
|
Displacement of [3H]PCP from nAChR in Torpedo nobiliana electric organs membranes assessed as [3H]PCP binding level at 300 uM pre-treated with 0.5 uM alpha-bungarotoxin by scintillation counting method relative to untreated control
|
Torpedo nobiliana
|
142.0
%
|
|
Journal : J Pesticide Sci
Title : Pharmacological Effects of Imidacloprid and Its Related Compounds on the Nicotinic Acetyicholine Receptor with Its Ion Channel from the Torpedo Electric Organ
Year : 1995
Volume : 20
Issue : 1
First Page : 49
Last Page : 56
Authors : TOMIZAWA M, OTSUKA H, MIYAMOTO T, YAMAMOTO I
|
Displacement of [3H]PCP from nAChR in Torpedo nobiliana electric organs membranes assessed as [3H]PCP binding level at 300 uM in presence of 100 uM carbachol by scintillation counting method relative to untreated control
|
Torpedo nobiliana
|
94.6
%
|
|
Journal : J Pesticide Sci
Title : Pharmacological Effects of Imidacloprid and Its Related Compounds on the Nicotinic Acetyicholine Receptor with Its Ion Channel from the Torpedo Electric Organ
Year : 1995
Volume : 20
Issue : 1
First Page : 49
Last Page : 56
Authors : TOMIZAWA M, OTSUKA H, MIYAMOTO T, YAMAMOTO I
|
Displacement of [3H]PCP from nAChR in Torpedo nobiliana electric organs membranes assessed as [3H]PCP binding level at 300 uM by scintillation counting method relative to untreated control
|
Torpedo nobiliana
|
461.0
%
|
|
Journal : J Pesticide Sci
Title : Pharmacological Effects of Imidacloprid and Its Related Compounds on the Nicotinic Acetyicholine Receptor with Its Ion Channel from the Torpedo Electric Organ
Year : 1995
Volume : 20
Issue : 1
First Page : 49
Last Page : 56
Authors : TOMIZAWA M, OTSUKA H, MIYAMOTO T, YAMAMOTO I
|
Displacement of [3H]alpha-BGT from nAChR in Torpedo nobiliana electric organs membranes by scintillation counting method
|
Torpedo nobiliana
|
676000.0
nM
|
|
Journal : J Pesticide Sci
Title : Pharmacological Effects of Imidacloprid and Its Related Compounds on the Nicotinic Acetyicholine Receptor with Its Ion Channel from the Torpedo Electric Organ
Year : 1995
Volume : 20
Issue : 1
First Page : 49
Last Page : 56
Authors : TOMIZAWA M, OTSUKA H, MIYAMOTO T, YAMAMOTO I
|
Displacement of [3H]alpha-BGT from nAChR in Apis mellifera (honeybee) head homogenates
|
Apis mellifera
|
26.0
nM
|
|
Journal : J Pesticide Sci
Title : Pharmacological Characteristics of Insect Nicotinic Acetyicholine Receptor with Its Ion Channel and the Comparison of the Effect of Nicotinoids and Neonicotinoids
Year : 1995
Volume : 20
Issue : 1
First Page : 57
Last Page : 64
Authors : TOMIZAWA M, OTSUKA H, MIYAMOTO T, ELDEFRAWI ME, YAMAMOTO I
|
Displacement of [3H]PCP from nAChR in Apis mellifera (honeybee0 head homogenates
|
Apis mellifera
|
953000.0
nM
|
|
Journal : J Pesticide Sci
Title : Pharmacological Characteristics of Insect Nicotinic Acetyicholine Receptor with Its Ion Channel and the Comparison of the Effect of Nicotinoids and Neonicotinoids
Year : 1995
Volume : 20
Issue : 1
First Page : 57
Last Page : 64
Authors : TOMIZAWA M, OTSUKA H, MIYAMOTO T, ELDEFRAWI ME, YAMAMOTO I
|
Hydrophobicity, log K of the compound by HPLC
|
None
|
0.05
|
|
Journal : J Pesticide Sci
Title : Actions of imidacloprid, clothianidin and related neonicotinoids on nicotinic acetylcholine receptors of American cockroach neurons and their relationships with insecticidal potency
Year : 2006
Volume : 31
Issue : 1
First Page : 35
Last Page : 40
Authors : Ihara M, Brown LA, Ishida C, Okuda H, Sattelle DB, Matsuda K
|
Insecticidal activity against Periplaneta americana (American cockroach) assessed as killing measured per insect at 25 to 28 degC for 24 hr in presence of piperonyl butoxide
|
Periplaneta americana
|
10.1
|
|
Journal : J Pesticide Sci
Title : Actions of imidacloprid, clothianidin and related neonicotinoids on nicotinic acetylcholine receptors of American cockroach neurons and their relationships with insecticidal potency
Year : 2006
Volume : 31
Issue : 1
First Page : 35
Last Page : 40
Authors : Ihara M, Brown LA, Ishida C, Okuda H, Sattelle DB, Matsuda K
|
Agonist activity at Periplaneta americana (American cockroach) nAChR in terminal abdominal ganglion assessed as assessed as inward current by tight-seal whole cell patch clamp method relative to 100 uM ACh
|
Periplaneta americana
|
0.24
|
|
Journal : J Pesticide Sci
Title : Actions of imidacloprid, clothianidin and related neonicotinoids on nicotinic acetylcholine receptors of American cockroach neurons and their relationships with insecticidal potency
Year : 2006
Volume : 31
Issue : 1
First Page : 35
Last Page : 40
Authors : Ihara M, Brown LA, Ishida C, Okuda H, Sattelle DB, Matsuda K
|
Agonist activity at Periplaneta americana (American cockroach) nAChR in terminal abdominal ganglion assessed as assessed as inward current by tight-seal whole cell patch clamp method
|
Periplaneta americana
|
72.44
nM
|
|
Journal : J Pesticide Sci
Title : Actions of imidacloprid, clothianidin and related neonicotinoids on nicotinic acetylcholine receptors of American cockroach neurons and their relationships with insecticidal potency
Year : 2006
Volume : 31
Issue : 1
First Page : 35
Last Page : 40
Authors : Ihara M, Brown LA, Ishida C, Okuda H, Sattelle DB, Matsuda K
