Discovery and Characterization of Sulfoxaflor, a Novel Insecticide Targeting Sap-Feeding Pests

Yuanming Zhu; Michael R. Loso; Gerald B. Watson; Thomas C. Sparks; Richard B. Rogers; Jim X. Huang; B. Clifford Gerwick; Jonathan M. Babcock; Donald Kelley; Vidyadhar B. Hegde; Benjamin M. Nugent; James M. Renga; Ian Denholm; Kevin Gorman; Gerrit J. DeBoer; James Hasler; Thomas Meade; James D. Thomas

doi:10.1021/jf102765x

Discovery and Characterization of Sulfoxaflor, a Novel Insecticide Targeting Sap-Feeding Pests

Yuanming Zhu, Michael R. Loso, Gerald B. Watson, Thomas C. Sparks, Richard B. Rogers, Jim X. Huang, B. Clifford Gerwick, Jonathan M. Babcock, Donald Kelley, Vidyadhar B. Hegde, Benjamin M. Nugent, James M. Renga, Ian Denholm, Kevin Gorman, Gerrit J. DeBoer, James Hasler, Thomas Meade, James D. Thomas

Research output: Contribution to journal › Article › peer-review

221 Citations (Scopus)

Abstract

The discovery of sulfoxaflor [N-[methyloxido[1-[6-(trifluoromethyl)-3-pyridinyl]ethyl]-lambda(4)-sulfanylidene] cyanamide] resulted from an investigation of the sulfoximine functional group as a novel bioactive scaffold for insecticidal activity and a subsequent extensive structure activity relationship study. Sulfoxaflor, the first product from this new class (the sulfoximines) of insect control agents, exhibits broad-spectrum efficacy against many sap-feeding insect pests, including aphids, whiteflies, hoppers, and Lygus, with levels of activity that are comparable to those of other classes of insecticides targeting sap-feeding insects, including the neonicotinoids. However, no cross-resistance has been observed between sulfoxaflor and neonicotinoids such as imidacloprid, apparently the result of differences in susceptibility to oxidative metabolism. Available data are consistent with sulfoxaflor acting via the insect nicotinic receptor in a complex manner. These observations reflect the unique structure of the sulfoximines compared with neonicotinoids.

Original language	English
Pages (from-to)	2950-2957
Number of pages	8
Journal	Journal of Agricultural and Food Chemistry
Volume	59
Issue number	7
DOIs	https://doi.org/10.1021/jf102765x
Publication status	Published - 13 Apr 2011

Keywords

DROSOPHILA
NEONICOTINOID INSECTICIDES
SULFIDES
MYZUS-PERSICAE
NICOTINIC ACETYLCHOLINE-RECEPTORS
insecticide resistance
sulfoximines
Q-BIOTYPE
HEMIPTERA APHIDIDAE
sulfoxaflor
RESISTANCE
EXPRESSION
Myzus persicae
BEMISIA-TABACI
nicotinic acetylcholine receptor

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Zhu, Y., Loso, M. R., Watson, G. B., Sparks, T. C., Rogers, R. B., Huang, J. X., Gerwick, B. C., Babcock, J. M., Kelley, D., Hegde, V. B., Nugent, B. M., Renga, J. M., Denholm, I., Gorman, K., DeBoer, G. J., Hasler, J., Meade, T., & Thomas, J. D. (2011). Discovery and Characterization of Sulfoxaflor, a Novel Insecticide Targeting Sap-Feeding Pests. Journal of Agricultural and Food Chemistry, 59(7), 2950-2957. https://doi.org/10.1021/jf102765x

@article{2549be15dc324615a1b1bf26b6996902,

title = "Discovery and Characterization of Sulfoxaflor, a Novel Insecticide Targeting Sap-Feeding Pests",

abstract = "The discovery of sulfoxaflor [N-[methyloxido[1-[6-(trifluoromethyl)-3-pyridinyl]ethyl]-lambda(4)-sulfanylidene] cyanamide] resulted from an investigation of the sulfoximine functional group as a novel bioactive scaffold for insecticidal activity and a subsequent extensive structure activity relationship study. Sulfoxaflor, the first product from this new class (the sulfoximines) of insect control agents, exhibits broad-spectrum efficacy against many sap-feeding insect pests, including aphids, whiteflies, hoppers, and Lygus, with levels of activity that are comparable to those of other classes of insecticides targeting sap-feeding insects, including the neonicotinoids. However, no cross-resistance has been observed between sulfoxaflor and neonicotinoids such as imidacloprid, apparently the result of differences in susceptibility to oxidative metabolism. Available data are consistent with sulfoxaflor acting via the insect nicotinic receptor in a complex manner. These observations reflect the unique structure of the sulfoximines compared with neonicotinoids.",

keywords = "DROSOPHILA, NEONICOTINOID INSECTICIDES, SULFIDES, MYZUS-PERSICAE, NICOTINIC ACETYLCHOLINE-RECEPTORS, insecticide resistance, sulfoximines, Q-BIOTYPE, HEMIPTERA APHIDIDAE, sulfoxaflor, RESISTANCE, EXPRESSION, Myzus persicae, BEMISIA-TABACI, nicotinic acetylcholine receptor",

author = "Yuanming Zhu and Loso, {Michael R.} and Watson, {Gerald B.} and Sparks, {Thomas C.} and Rogers, {Richard B.} and Huang, {Jim X.} and Gerwick, {B. Clifford} and Babcock, {Jonathan M.} and Donald Kelley and Hegde, {Vidyadhar B.} and Nugent, {Benjamin M.} and Renga, {James M.} and Ian Denholm and Kevin Gorman and DeBoer, {Gerrit J.} and James Hasler and Thomas Meade and Thomas, {James D.}",

year = "2011",

month = apr,

day = "13",

doi = "10.1021/jf102765x",

language = "English",

volume = "59",

pages = "2950--2957",

journal = "Journal of Agricultural and Food Chemistry",

issn = "0021-8561",

publisher = "American Chemical Society (ACS)",

number = "7",

}

Zhu, Y, Loso, MR, Watson, GB, Sparks, TC, Rogers, RB, Huang, JX, Gerwick, BC, Babcock, JM, Kelley, D, Hegde, VB, Nugent, BM, Renga, JM, Denholm, I, Gorman, K, DeBoer, GJ, Hasler, J, Meade, T & Thomas, JD 2011, 'Discovery and Characterization of Sulfoxaflor, a Novel Insecticide Targeting Sap-Feeding Pests', Journal of Agricultural and Food Chemistry, vol. 59, no. 7, pp. 2950-2957. https://doi.org/10.1021/jf102765x

TY - JOUR

T1 - Discovery and Characterization of Sulfoxaflor, a Novel Insecticide Targeting Sap-Feeding Pests

AU - Zhu, Yuanming

AU - Loso, Michael R.

AU - Watson, Gerald B.

AU - Sparks, Thomas C.

AU - Rogers, Richard B.

AU - Huang, Jim X.

AU - Gerwick, B. Clifford

AU - Babcock, Jonathan M.

AU - Kelley, Donald

AU - Hegde, Vidyadhar B.

AU - Nugent, Benjamin M.

AU - Renga, James M.

AU - Denholm, Ian

AU - Gorman, Kevin

AU - DeBoer, Gerrit J.

AU - Hasler, James

AU - Meade, Thomas

AU - Thomas, James D.

PY - 2011/4/13

Y1 - 2011/4/13

N2 - The discovery of sulfoxaflor [N-[methyloxido[1-[6-(trifluoromethyl)-3-pyridinyl]ethyl]-lambda(4)-sulfanylidene] cyanamide] resulted from an investigation of the sulfoximine functional group as a novel bioactive scaffold for insecticidal activity and a subsequent extensive structure activity relationship study. Sulfoxaflor, the first product from this new class (the sulfoximines) of insect control agents, exhibits broad-spectrum efficacy against many sap-feeding insect pests, including aphids, whiteflies, hoppers, and Lygus, with levels of activity that are comparable to those of other classes of insecticides targeting sap-feeding insects, including the neonicotinoids. However, no cross-resistance has been observed between sulfoxaflor and neonicotinoids such as imidacloprid, apparently the result of differences in susceptibility to oxidative metabolism. Available data are consistent with sulfoxaflor acting via the insect nicotinic receptor in a complex manner. These observations reflect the unique structure of the sulfoximines compared with neonicotinoids.

AB - The discovery of sulfoxaflor [N-[methyloxido[1-[6-(trifluoromethyl)-3-pyridinyl]ethyl]-lambda(4)-sulfanylidene] cyanamide] resulted from an investigation of the sulfoximine functional group as a novel bioactive scaffold for insecticidal activity and a subsequent extensive structure activity relationship study. Sulfoxaflor, the first product from this new class (the sulfoximines) of insect control agents, exhibits broad-spectrum efficacy against many sap-feeding insect pests, including aphids, whiteflies, hoppers, and Lygus, with levels of activity that are comparable to those of other classes of insecticides targeting sap-feeding insects, including the neonicotinoids. However, no cross-resistance has been observed between sulfoxaflor and neonicotinoids such as imidacloprid, apparently the result of differences in susceptibility to oxidative metabolism. Available data are consistent with sulfoxaflor acting via the insect nicotinic receptor in a complex manner. These observations reflect the unique structure of the sulfoximines compared with neonicotinoids.

KW - DROSOPHILA

KW - NEONICOTINOID INSECTICIDES

KW - SULFIDES

KW - MYZUS-PERSICAE

KW - NICOTINIC ACETYLCHOLINE-RECEPTORS

KW - insecticide resistance

KW - sulfoximines

KW - Q-BIOTYPE

KW - HEMIPTERA APHIDIDAE

KW - sulfoxaflor

KW - RESISTANCE

KW - EXPRESSION

KW - Myzus persicae

KW - BEMISIA-TABACI

KW - nicotinic acetylcholine receptor

U2 - 10.1021/jf102765x

DO - 10.1021/jf102765x

M3 - Article

SN - 0021-8561

VL - 59

SP - 2950

EP - 2957

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

IS - 7

ER -

Discovery and Characterization of Sulfoxaflor, a Novel Insecticide Targeting Sap-Feeding Pests

Abstract

Keywords

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