Progress in Plant Protection

Neonicotinoids – systemic insecticides in plant protection
Neonikotynoidy – insektycydy systemiczne w ochronie roślin

Monika Michel, e-mail: M.Michel@iorpib.poznan.pl

Instytut Ochrony Roślin - Państwowy Instytut Badawczy, Władysława Węgorka 20, 60-318 Poznań, Polska
Streszczenie

Neonicotinoids are the active substances of systemic insecticides that have a neuroactive effect, used in plant protection products to combat harmful insects. The aim of the study was to present synthetically the most important aspects regarding the properties of neonicotinoid compounds, their applications and analytical methods for determination based on a review of selected world literature.

 

Neonikotynoidy to substancje czynne insektycydów systemicznych o działaniu neuroaktywnym, stosowane w środkach ochrony roślin do zwalczania szkodliwych owadów. Celem pracy było syntetyczne przedstawienie najistotniejszych aspektów dotyczących właściwości związków neonikotynoidowych, ich zastosowania i analitycznych metod oznaczania w oparciu o przegląd wybranej literatury światowej.

Słowa kluczowe
neonicotionids; plant protection; physico-chemical characteristic; mode of action; residue determination; neonikotynoidy; ochrona roślin; charakterystyka fizykochemiczna; sposób działania; oznaczanie pozostałości
Referencje

Blasco C., Fernández M., Picó Y., Font G., Mańes J. 2002. Simultaneous determination of imidacloprid, carbendazim, methiocarb and hexythiazox in peaches and nectarines by liquid chromatography – mass spectrometry. Analytica Chimica Acta 461 (1): 109–116. DOI: 10.1016/S0003­-2670(02)00255-­6

 

Byrne F.J., Toscano N.C., Urena A.A., Morse J.G. 2005. Quantification of imidacloprid toxicity to avocado thrips, Scirtothrips perseae Nakahara (Thysanoptera: Thripidae), using a combined bioassay and ELISA approach. Pest Management Science 61 (8): 754–758. DOI: 10.1002/ps.1052

 

Casida J.E. 2010. Neonicotinoid metabolism: compounds, substituents, pathways, enzymes, organisms, and relevance. Journal of Agricultural and Food Chemistry 59 (7): 2923–2931. DOI: 10.1021/jf102438c

 

Casida J.E., Durkin K. 2013. Neuroactive insecticides: targets, selectivity, resistance, and secondary effects. Annual Review of Entomology 58: 99–117. DOI: 10.1146/annurev­-ento-­120811-­153645

 

Cutler P., Slater R., Edmunds J.F., Maienfisch P., Hall R.G., Earley G.P., Pitterna T., Pal S., Paul V.­-L., Goodchild J., Blacker M., Hagmann L., Crossthwaite A.J. 2013. Investigating the mode of action of sulfoxaflor: a fourth­generation neonicotinoid. Pest Management Science 69 (5): 607–619. DOI: 10.1002/ps.3413

 

EFSA 2013. EFSA identifies risks to bees from neonicotinoids. https://www.efsa.europa.eu/en/press/news/130116 [dostęp: 16.01.2013].

 

Eisenback B.M., Mullins D.E., Salom S.M., Kok L.T. 2008. Evaluation of ELISA for imidacloprid detection in eastern hemlock (Tsuga canadensis) wood and needle tissues. Pest Management Science 65 (2): 122–128. DOI: 10.1002/ps.1655

 

Fernández­-Alba A.R., Tejedor A., Agüera A., Contreras M., Garrido J. 2000. Determination of imidacloprid and benzimidazole residues in fruits and vegetables by liquid chromatography – mass spectrometry after ethyl acetate multiresidue extraction. Journal of AOAC International 83 (3): 748–755.

 

Ferrer I., Thurman E.M. 2007. Multi­-residue method for the analysis of 101 pesticides and their degradates in food and water samples by liquid chromatography/time­-of-­flight mass spectrometry. Journal of Chromatography A 1175 (1): 24–37. DOI: 10.1016/j. chroma.2007.09.092

 

Ferrier P.M., Rucker R.R., Thurman W.N., Burgett M. 2018. Economic Effects and Responses to Changes in Honey Bee Health. Economic Research Report 246. United States Department of Agriculture, Economic Research Service, March 2018, 54 ss.

 

Ford K.A., Casida J.E. 2008. Comparative metabolism and pharmacokinetics of seven neonicotinoid insecticides in spinach. Journal of Agricultural and Food Chemistry 56 (21): 10168–10175. DOI: 10.1021/jf8020909

 

Frenich A.G., Vidal J.L.M., Pastor­-Montoro E., Romero­-González R. 2008. High­-throughput determination of pesticide residues in food commodities by use of ultra­-performance liquid chromatography – tandem mass spectrometry. Analytical and Bioanalytical Chemistry 390 (3): 947–959. DOI: 10.1007/s00216­-007-­1746-­5

 

García­-Chao M., Agruńa M.J., Calvete G.F., Sakkas V., Llompart M., Dagnac T. 2010. Validation of an off line solid phase extraction liquid chromatography – tandem mass spectrometry method for the determination of systemic insecticide residues in honey and pollen samples collected in apiaries from NW Spain. Analytica Chimica Acta 672 (1–2): 107–113. DOI: 10.1016/j.aca.2010.03.011

 

Jeschke P., Nauen R. 2008. Neonicotinoids – from zero to hero in insecticide chemistry. Pest Management Science 64 (11): 1084–1098. DOI: 10.1002/ps.1631

 

Kagabu S. 1996. Studies on the synthesis and insecticidal activity of neonicotinoid compounds. Journal of Pesticide Science 21 (2): 231–239. DOI: 10.1584/jpestics.21.231

 

Kagabu S., Moriya K., Shibuya K., Hattori Y., Tsuboi S., Shiokawa K. 1992. 1­-(6-­halonicotinyl-­2-­nitromethylene­imidazolidines as potential new insecticides. Bioscience, Biotechnology, and Biochemistry 56 (2): 362–363. DOI: 10.1271/bbb.56.362

 

Kamel A. 2010. Refined methodology for the determination of neonicotinoid pesticides and their metabolites in honey bees and bee products by liquid chromatography – tandem mass spectrometry (LC­MS/MS). Journal of Agricultural and Food Chemistry 58 (10): 5926–5931. DOI: 10.1021/jf904120n

 

Kim H.­-J., Shelver W.L., Hwang E.-­C., Xu T., Li Q.X. 2006. Automated flow fluorescent immunoassay for part per trillion detection of the neonicotinoid insecticide thiamethoxam. Analytica Chimica Acta 571 (1): 66–73. DOI: 10.1016/j.aca.2006.04.084

 

Kmellár B., Fodor P., Pareja L., Ferrer C., Martínez­-Uroz M.A., Valverde A., Fernandez-­Alba A.R. 2008. Validation and uncertainty study of a comprehensive list of 160 pesticide residues in multi­class vegetables by liquid chromatography – tandem mass spectrometry. Journal of Chromatography A 1215 (1–2): 37–50. DOI: 10.1016/j.chroma.2008.10.121

 

Kmellár B., Pareja L., Ferrer C., Fodor P., Fernandez­-Alba A.R. 2011. Study of the effects of operational parameters on multiresidue pesticide analysis by LC­-MS/MS. Talanta 84 (2): 262–273. DOI: 10.1016/j.talanta.2010.12.006

 

Lara F.J., García­-Campańa A.M., Aaron J.-­J. 2010. Analytical applications of photoinduced chemiluminescence in flow systems – A review. Analytica Chimica Acta 679 (1–2): 17–30. DOI: 10.1016/j.aca.2010.09.001

 

Lehotay S.J., de Kok A., Hiemstra M., van Bodegraven P. 2005. Validation of a fast and easy method for the determination of residues from 229 pesticides in fruits and vegetables using gas and liquid chromatography and mass spectrometric detection. Journal of AOAC International 88 (2): 595–614.

 

Liu H., Song J., Zhang S., Qu L., Zhao Y., Wu Y., Liu H. 2005. Analysis of residues of imidacloprid in tobacco by high­performance liquid chromatography with liquid­-liquid partition cleanup. Pest Management Science 61 (5): 511–514. DOI: 10.1002/ps.987

 

Llorent­-Martínez E.J., Ortega­-Barrales P., Fernández-­de Córdova M.L., Ruiz-­Medina A. 2011. Trends in flow­-based analytical methods applied to pesticide detection: A review. Analytica Chimica Acta 684 (1–2): 30–39. DOI: 10.1016/j.aca.2010.10.036

 

Ma H., Xu Y., Li Q.X., Xu T., Wang X., Li J. 2009. Application of enzyme-­linked immunosorbent assay for quantification of the insecticides imidacloprid and thiamethoxam in honey samples. Food Additives and Contaminants: Part A 26 (5): 713–718. DOI: 10.1080/02652030802672638

 

MacBean C. (red.). 2012. A World Compendium. The Pesticide Manual. Sixteenth Edition. British Crop Production Council, Hampshire, UK, 561 ss. ISBN 978­-1901396-­86-­7.

 

MacDonald L.M., Meyer T.R. 1998. Determination of imidacloprid and triadimefon in white pine by gas chromatography/mass spectrometry. Journal of Agricultural and Food Chemistry 46 (8): 3133–3138. DOI: 10.1021/jf9800357

 

MRiRW 2018. Krajowy plan działania na rzecz ograniczenia ryzyka związanego ze stosowaniem środków ochrony roślin na lata 2018–2022. https://www.gov.pl/web/rolnictwo/stosowanie­-srodkow­-ochrony-­roslin­krajowy-­plan-­dzialania [dostęp: 17.07.2018].

 

Payá P., Anastassiades M., Mack D., Sigalova I., Tasdelen B., Oliva J., Barba A. 2007. Analysis of pesticide residues using the Quick Easy Cheap Effective Rugged and Safe (QuEChERS) pesticide multiresidue method in combination with gas and liquid chromatography and tandem mass spectrometric detection. Analytical and Bioanalytical Chemistry 389 (6): 1697–1714. DOI: 10.1007/s00216­-007-1610-­7

 

Pous X., Ruís M.J., Picó Y., Font G. 2001. Determination of imidacloprid, metalaxyl, myclobutanil, propham, and thiabendazole in fruits and vegetables by liquid chromatography – atmospheric pressure chemical ionization­mass spectrometry. Fresenius Journal of Analytical Chemistry 371 (2): 182–189. DOI: 10.1007/s002160100946

 

Radišić M., Grujić S., Vasiljević T., Laušević M. 2009. Determination of selected pesticides in fruit juices by matrix solid­-phase dispersion and liquid chromatography – tandem mass spectrometry. Food Chemistry 113 (2): 712–719. DOI: 10.1016/j.foodchem.2008.07.103

 

Romero­-González R., Frenich A.G., Vidal J.L.M., Prestes O.D., Grio S.L. 2011. Simultaneous determination of pesticides, biopesticides and mycotoxins in organic products applying a quick, easy, cheap, effective, rugged and safe extraction procedure and ultra­-high performance liquid chromatography – tandem mass spectrometry. Journal of Chromatography A 1218 (11): 1477–1485. DOI: 10.1016/j.chroma.2011.01.034

 

Shiokawa K., Tsuboi S., Iwaya K., Moriya K. 1994. Development of a chloronicotinyl insecticide, imidacloprid. Journal of Pesticide Science 19 (4): S209–S217. DOI: 10.1584/jpestics.19.4_S209

 

Shiokawa K., Tsuboi S., Kagabu S., Moriya K. 1986. (Nikon Bayer Agrochem K. K.): Jpn. Kokai Tokkyo Koho JP 61­-267575.

 

Singh S.B., Foster G.D., Khan S.U. 2004. Microwave­-assisted extraction for the simultaneous determination of thiamethoxam, imidacloprid, and carbendazim residues in fresh and cooked vegetable samples. Journal of Agricultural and Food Chemistry 52 (1): 105–109. DOI: 10.1021/jf030358p

 

Soloway S.B., Henry A.C., Kollmeyer W.D., Padgett W.M., Powell J.E., Roman S.A., Tieman C.H., Corey R.A., Horne C.A. 1978. Nitromethylene heterocycles as insecticides. s. 153–158. W: Pesticide and Venom Neurotoxicity (D.L. Shankland, R.M. Hollingworth, T. Smith Jr., red.). Springer US, Plenum Press, New York, 284 ss. ISBN 978­-1-­4615-­8834-­4. DOI: 10.1007/978-­1-­4615-­8834-­4

 

Soloway S.B., Henry A.C., Kollmeyer W.D., Padgett W.M., Powell J.E., Roman S.A., Tieman C.H., Corey R.A., Horne C.A. 1979. Nitromethylene insecticides. s. 206–217. W: Advances in Pesticide Science (H. Geissbüehler, G.T. Brooks, P.C. Kearney, red.). Pergamon Press, Oxford, 522 ss. ISBN 978­-0080239309.

 

Tomizawa M. 1994. Structure–activity relationships of nicotinoids and the related compounds. Journal of Pesticide Science 19 (4): S229–S240. DOI: 10.1584/jpestics.19.4_S229

 

Tomizawa M., Casida J.E. 2011. Neonicotinoid insecticides: highlights of a symposium on strategic molecular designs. Journal of Agricultural and Food Chemistry 59 (7): 2883–2886. DOI: 10.1021/jf103856c

 

Tomizawa M., Casida J.E. 2005. Neonicotinoid insecticide toxicology: Mechanisms of selective action. Annual Review of Pharmacology and Toxicology 45: 247–268. DOI: 10.1146/annurev.pharmtox.45.120403.095930

 

Totti S., Fernández M., Ghini S., Picó Y., Fini F., Mańes J., Girotti S. 2006. Application of matrix solid phase dispersion to the determination of imidacloprid, carbaryl, aldicarb, and their main metabolites in honeybees by liquid chromatography – mass spectrometry detection. Talanta 69 (3): 724–729. DOI: 10.1016/j.talanta.2005.11.012

 

Vilchez J.L., Valencia M.C., Navalón A., Molinero­-Morales B., Capitán­-Vallvey L.F. 2001. Flow injection analysis of the insecticide imidacloprid in water samples with photochemically induced fluorescence detection. Analytica Chimica Acta 439 (2): 299–305. DOI: 10.1016/S0003­-2670(01)01039-­X

 

Watanabe E. 2012. Review on Current Analytical Methods with Chromatographic and Nonchromatographic Techniques for New Generation Insecticide Neonicotinoids. s. 482–510. W: Insecticides – Advances in Integrated Pest Management (F. Perveen, red.). InTech, Rijeka, Croatia, 708 ss. ISBN 978­-953-­307-­780-­2.

 

Watanabe E., Baba K., Eun H. 2007. Simultaneous determination of neonicotinoid insecticides in agricultural samples by solid­-phase extraction cleanup and liquid chromatography equipped with diode­-array detection. Journal of Agricultural and Food Chemistry 55 (10): 3798–3804. DOI: 10.1021/jf063140m

 

Xu T., Jacobsen C.M., Cho I.K., Hara A.H., Li Q.X. 2006. Application of an enzyme­-linked immunosorbent assay for the analysis of imidacloprid in wiliwili tree, Erythrina sandwicensis O. Deg, for control of the wasp Quadrastichus erythrinae. Journal of Agricultural and Food Chemistry 54 (22): 8444–8449. DOI: 10.1021/jf062004e

 

Xu T., Wei K.­-Y., Wang J., Ma H.-­X., Li J., Xu Y.-­J., Li Q.X. 2010. Quantitative analysis of the neonicotinoid insecticides imidacloprid and thiamethoxam in fruit juices by enzyme­-linked immunosorbent assays. Journal of AOAC International 93 (1): 12–18.

Progress in Plant Protection (2020) : 0-0
Data pierwszej publikacji on-line: 2020-02-28 11:54:47
htpp://dx.doi.org/10.14199/ppp-2020-006
Pełny tekst (.PDF) BibTeX Mendeley Powrót do listy