sulfoxaflor: insecticide targeting sap-feeding pests; structure in first source
sulfoxaflor : A mixture of the four diastereoisomers arising from the two tetrahedral stereocentres of [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide (the sulfur atom and the carbon attached to position 3 of the pyridine ring). [Both E- and Z-isomers involving the S=N double bond and the cyano group exist, but they interconvert rapidly at r.t.]. A nicotinic acetylcholine receptor agonist in insects, sulfoxaflor is used as an insecticide, particularly for the control of aphids.
[methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide : A member of the class of pyridines that is 5-ethyl-2-trifluoromethylpyridine in which the ethyl group is substituted at position 1 by an N-cyano-S-methylsulfonimidoyl group. The insecticide sulfoxalor is a mixture of the four possible stereoisomers arising from the two tetrahedral stereocentres.
ID Source | ID |
---|---|
PubMed CID | 16723172 |
CHEMBL ID | 2230078 |
CHEBI ID | 133306 |
SCHEMBL ID | 520711 |
MeSH ID | M0560136 |
Synonym |
---|
CHEBI:133306 |
[methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide |
gf 2372 |
sulfoxaflor [iso] |
n-(methyloxido(1-(6-(trifluoromethyl)-3-pyridinyl)ethyl)-lambda4-sulfanylidene)cyanamide |
xde 208 |
gf 2032 |
unii-671w88oy8k |
946578-00-3 |
sulfoxaflor |
671w88oy8k , |
hsdb 8245 |
sulfoxaflor b |
transform |
sulfoxaflor a |
cyanamide, n-(methyloxido(1-(6-(trifluoromethyl)-3-pyridinyl)ethyl)-.lambda.4-sulfanylidene)- |
xde-208 |
methyl(1-(2-trifluoromethylpyridin-5-yl)ethyl)-n-cyanosulfoximine |
gf-2372 |
gf-2032 |
SCHEMBL520711 |
CHEMBL2230078 |
DTXSID0074687 |
AKOS027322695 |
[methyl(oxo){1-[6-(trifluoromethyl)-3-pyridyl]ethyl}-lambda6-sulfanylidene]cyanamide |
n-[methyl-oxo-[1-[6-(trifluoromethyl)-3-pyridyl]ethyl]-lambda6-sulfanylidene]cyanamide |
gf 2032; gf 2372; methyl[1-(2-trifluoromethylpyridin-5-yl)ethyl]-n-cyanosulfoximine; sulfoxaflor; transform; xde 208, cyanamide, n-[methyloxido[1-[6-(trifluoromethyl)-3-pyridinyl]ethyl]-?4-sulfanylidene]- |
[methyl-oxo-[1-[6-(trifluoromethyl)pyridin-3-yl]ethyl]-lambda6-sulfanylidene]cyanamide |
HY-118504 |
sulfoxaflor 100 microg/ml in acetonitrile |
Q14566721 |
gf 2032; gf 2372; xde 208 |
CS-0066179 |
n-(methyl(oxo)(1-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-l6-sulfanylidene)cyanamide |
cyanamide,n-[methyloxido[1-[6-(trifluoromethyl)-3-pyridinyl]ethyl]-l4-sulfanylidene]- |
WMB57800 |
cyanamide, n-[methyloxido[1-[6-(trifluoromethyl)-3-pyridinyl]ethyl]-.lamda.4-sulfanylidene]- |
Z3244811863 |
1ST20444 |
Sulfoxaflor is a fourth-generation neonicotinoid insecticide mainly used to control sap-feeding pests. It acts on the nicotinic acetylcholine receptor (nAChRs) in a similar way to neonicsotinoids. Sulfoxflor is widely used pesticide in agriculture.
Excerpt | Reference | Relevance |
---|---|---|
"Sulfoxaflor has been considered as a new tool for Nilaparvata lugens control in the field. " | ( Inheritance and fitness costs of sulfoxaflor resistance in Nilaparvata lugens (Stål). Ali, E; Jin, R; Li, J; Li, W; Li, Z; Liao, X; Mao, K; Wan, H, 2019) | 2.24 |
Excerpt | Reference | Relevance |
---|---|---|
"Sulfoxaflor showed lower lethality than imidacloprid to midges, with LC50 values of 84.1 (81.5-87.3), 66.3 (34.8-259), and 47.5 (29.5-306) μg/L for 96-h, 10-d, and 23-d exposures, respectively." | ( The neonicotinoid alternative sulfoxaflor causes chronic toxicity and impairs mitochondrial energy production in Chironomus kiinensis. Li, H; Liu, P; Wu, F; You, J, 2021) | 1.63 |
Excerpt | Reference | Relevance |
---|---|---|
"Sulfoxaflor treatment for 14 days led to reduced aggressiveness of S." | ( Toxicity and sublethal effects of sulfoxaflor on the red imported fire ant, Solenopsis invicta. Lu, Y; Pan, F; Wang, L, 2017) | 1.46 |
Sulfoxaflor can help assess the potential ecological risk of chiral pesticides to aquatic organisms.
Excerpt | Reference | Relevance |
---|---|---|
" This study provides important information on the enantioselective behavior and toxic effects of sulfoxaflor, which can help assess the potential ecological risk of chiral pesticides to aquatic organisms." | ( Enantioselective bioaccumulation and toxicity of rac-sulfoxaflor in zebrafish (Danio rerio). Chen, X; Deng, Y; Hu, D; Lu, P; Song, B; Wang, R; Xiao, X; Yang, Y, 2022) | 1.19 |
Excerpt | Reference | Relevance |
---|---|---|
" The proposed method was used to study the pharmacokinetic dissipation of sulfoxaflor stereoisomers in soil under greenhouse conditions." | ( Stereoselective separation and pharmacokinetic dissipation of the chiral neonicotinoid sulfoxaflor in soil by ultraperformance convergence chromatography/tandem mass spectrometry. Chen, Z; Cheng, Y; Dong, F; Liu, N; Liu, X; Pan, X; Tao, Y; Xu, J; Zheng, Y, 2014) | 0.86 |
Excerpt | Reference | Relevance |
---|---|---|
" Therefore, it is important to assess the potential effects of chronic exposure to sulfoxaflor, alone and in combination with fungicides, on pollinators." | ( Effects of chronic exposure to the new insecticide sulfoxaflor in combination with a SDHI fungicide in a solitary bee. Azpiazu, C; Bosch, J; Martins, C; Sgolastra, F, 2022) | 1.2 |
Excerpt | Relevance | Reference |
---|---|---|
" This finding triggered the inclusion of dose-response investigations of the potential key events for rodent liver carcinogenesis, concurrent with the hazard assessment studies." | ( An integrated approach for prospectively investigating a mode-of-action for rodent liver effects. Billington, R; Elcombe, C; Geter, DR; Gollapudi, BB; Kan, HL; LeBaron, MJ; McEwan, J; Murray, J; Rasoulpour, RJ; Terry, C; Thomas, J; Vardy, A; Wood, AJ, 2013) | 0.39 |
" The number of insects was counted before and 2, 3, 7 and 10 days after the application of pesticide in the test area within different dosage groups." | ( [Research on control effect of sulfoxaflor and flonicamid on Lonicera japonica]. Hou, SY; Li, JX; Wang, PS; Wang, YJ; Xue, J, 2018) | 0.77 |
Class | Description |
---|---|
pyridines | Any organonitrogen heterocyclic compound based on a pyridine skeleton and its substituted derivatives. |
sulfoximide | Compounds having the structure RS(=O)=NR. |
nitrile | A compound having the structure RC#N; thus a C-substituted derivative of hydrocyanic acid, HC#N. In systematic nomenclature, the suffix nitrile denotes the triply bound #N atom, not the carbon atom attached to it. |
organofluorine compound | An organofluorine compound is a compound containing at least one carbon-fluorine bond. |
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID1081834 | Insecticidal activity against DAS insecticide-resistant Bemisia tabaci B-biotype R-PBI (sweet potato whitefly) by leaf disk bioassay | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1081816 | Displacement of [3H]imidacloprid from nicotinic acetylcholine receptor in Myzus persicae (green peach aphid) homogenates by scintillation counting | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1081839 | Insecticidal activity against drug resistant Myzus persicae R-4013A (green peach aphid) by leaf disk bioassay | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1081840 | Insecticidal activity against Myzus persicae S-USIL (green peach aphid) by leaf disk bioassay | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1081818 | Drug metabolism in Drosophila melanogaster D.mel-2 cells over-expressing in CYP6G1 assessed as drug recovery measured 24 hr post dose by HPLC method | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1081826 | Resistance index, ratio of LC50 for drug resistant rothamsted-resistant Bemisia tabaci R-4991BT1 (sweet potato whitefly) to LC50 for DAS-susceptible Bemisia tabaci S-4971BT1 | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1081830 | Insecticidal activity against Bemisia tabaci SUD-S (sweet potato whitefly) by leaf disk bioassay | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1081821 | Insecticidal activity against Myzus persicae (green peach aphid) infested UV irradiated leaves of pepper plant exposed to compound at 124 ppm assessed as insect control efficacy post 3 days UV exposure relative to untreated control | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1081822 | Insecticidal activity against Myzus persicae (green peach aphid) infested UV irradiated leaves of pepper plant exposed to compound at 124 ppm assessed as insect control efficacy post 0 day UV exposure relative to untreated control | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1081841 | Insecticidal activity against Myzus persicae (green peach aphid) DAS lab strain by leaf disk bioassay | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1081838 | Insecticidal activity against Aphis gossypii (cotton aphid) DAS lab strain by leaf disk bioassay | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1081825 | Resistance index, ratio of LC50 for rothamsted-resistant Bemisia tabaci Q-biotype R-4971BT9 (sweet potato whitefly) to LC50 for Bemisia tabaci S-4971BT1 | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1112903 | Displacement of [3H]-methyl-SFX from nAChR in Myzus persicae 4106A (green peach aphid) membrane after 70 min | 2013 | Pest management science, May, Volume: 69, Issue:5 | Investigating the mode of action of sulfoxaflor: a fourth-generation neonicotinoid. |
AID1081836 | Insecticidal activity against Bemisia tabaci DAS (sweet potato whitefly) lab strain by leaf disk bioassay | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1112898 | Resistance index, ratio of LC50 for neonicotinoid-resistant Myzus persicae FRC-P (green peach aphid) to LC50 for Myzus persicae 4106A | 2013 | Pest management science, May, Volume: 69, Issue:5 | Investigating the mode of action of sulfoxaflor: a fourth-generation neonicotinoid. |
AID1112902 | Displacement of [3H]IMD from nAChR in Myzus persicae 4106A (green peach aphid) membrane after 70 min | 2013 | Pest management science, May, Volume: 69, Issue:5 | Investigating the mode of action of sulfoxaflor: a fourth-generation neonicotinoid. |
AID1112900 | Insecticidal activity against neonicotinoid-resistant Myzus persicae FRC-P (green peach aphid) fed on compound treated chinese cabbage discs after 72 hr | 2013 | Pest management science, May, Volume: 69, Issue:5 | Investigating the mode of action of sulfoxaflor: a fourth-generation neonicotinoid. |
AID1081828 | Resistance index, ratio of LC50 for drug resistant Myzus persicae R-4013A (green peach aphid) to LC50 for Myzus persicae S-USIL | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1081823 | Stability assessed as half life for photolysis in UV chamber at 1000 ppm by HPLC method | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1081837 | Insecticidal activity against Latrodectus hesperus DAS lab strain by leaf disk bioassay | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1081833 | Insecticidal activity against DAS-susceptible Bemisia tabaci S-4971BT1 (sweet potato whitefly) by leaf disk bioassay | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1112899 | Insecticidal activity against Myzus persicae 4106A (green peach aphid) fed on compound treated chinese cabbage discs after 72 hr | 2013 | Pest management science, May, Volume: 69, Issue:5 | Investigating the mode of action of sulfoxaflor: a fourth-generation neonicotinoid. |
AID1081829 | Insecticidal activity against rothamsted-resistant Bemisia tabaci Q-biotype R-CHLORAKA (sweet potato whitefly) by leaf disk bioassay | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1081824 | Resistance index, ratio of LC50 for rothamsted-resistant Bemisia tabaci Q-biotype R-CHLORAKA (sweet potato whitefly) to LC50 for Bemisia tabaci SUD-S | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1081832 | Insecticidal activity against rothamsted-resistant Bemisia tabaci R-4991BT1 (sweet potato whitefly) by leaf disk bioassay | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1081817 | Activation of Drosophila melanogaster nicotinic acetylcholine receptor alpha2 expressed in Xenopus laevis co-expressing chicken nicotinic acetylcholine receptor beta2 subunit by electrophysiology method | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1081819 | Drug metabolism in Drosophila melanogaster D.mel-2 cells deficient in CYP6G1 assessed as drug recovery measured 24 hr post dose by HPLC method | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1081842 | Insecticidal activity against Bemisia tabaci S-4971BT1 (sweet potato whitefly) by leaf disk bioassay | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1081831 | Insecticidal activity against rothamsted-resistant Bemisia tabaci Q-biotype R-4971BT9 (sweet potato whitefly) by leaf disk bioassay | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1081835 | Insecticidal activity against drug sensitive Bemisia tabaci DAS (sweet potato whitefly) lab strain by leaf disk bioassay | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1081827 | Resistance index, ratio of LC50 for DAS insecticide-resistant Bemisia tabaci B-biotype R-PB (sweet potato whitefly) to LC50 for drug sensitive Bemisia tabaci DAS lab strain | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
AID1081820 | Insecticidal activity against Myzus persicae (green peach aphid) infested UV irradiated leaves of pepper plant exposed to compound at 124 ppm assessed as insect control efficacy post 7 days UV exposure relative to untreated control | 2011 | Journal of agricultural and food chemistry, Apr-13, Volume: 59, Issue:7 | Discovery and characterization of sulfoxaflor, a novel insecticide targeting sap-feeding pests. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 0 (0.00) | 29.6817 |
2010's | 48 (37.21) | 24.3611 |
2020's | 81 (62.79) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.
| This Compound (38.82) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 6 (4.65%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 123 (95.35%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |