New piperidinium surfactants with carbamate fragments as effective adjuvants in insecticide compositions based on imidacloprid.

Item request has been placed! ×
Item request cannot be made. ×
loading   Processing Request
  • Additional Information
    • Source:
      Publisher: Published for SCI by Wiley Country of Publication: England NLM ID: 100898744 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1526-4998 (Electronic) Linking ISSN: 1526498X NLM ISO Abbreviation: Pest Manag Sci Subsets: MEDLINE
    • Publication Information:
      Original Publication: West Sussex, UK : Published for SCI by Wiley, c2000-
    • Subject Terms:
    • Abstract:
      Background: Surfactants, particularly non-ionic ones, are widely used as adjuvants in pesticide formulations due to their ability to maintain pesticide effectiveness without changing solution properties, such as pH. While non-ionic surfactants are generally low-toxic, stable, and excellent dispersants with high solubilization capabilities, they may be less effective than cationic surfactants, which offer superior surface activity, transport properties, and antimicrobial action. This study investigates the efficacy of new piperidinium surfactants with carbamate fragments as adjuvants in insecticide formulations containing imidacloprid. The efficacy of these formulations is being assessed against greenhouse whitefly, a pest known to harm cultivated and ornamental flowering plants.
      Results: The aggregation behavior of piperidinium surfactants containing carbamate fragments was investigated, and their wetting effect was evaluated. Synthesized surfactants have lower CMC values compared to their methylpiperidinium analogue. The effect of piperidinium surfactants on the insecticide concentration on the surface and inside tomato leaves was assessed using spectrophotometric methods. It was found that the introduction of piperidinium surfactants with carbamate fragment at a concentration of 0.1% wt. allows for decrease in lethal concentration of imidacloprid up to 10 times, thereby testifying the marked increase in the effectiveness of imidacloprid against the greenhouse whitefly insect pest (Trialeurodes vaporariorum). It was shown that the main factors responsible for the enhanced efficacy of the insecticide were the ability of the surfactant to increase the concentration of imidacloprid on the leaf surfaces and improve their penetration into the plant.
      Conclusion: The presented work employed a comprehensive approach, which significantly increases the generalizability of the results obtained and provides the ability to predict the effect and target selection of adjuvants. © 2024 Society of Chemical Industry.
      (© 2024 Society of Chemical Industry.)
    • References:
      Jibrin MO, Liu Q, Jones JB and Zhang S, Surfactants in plant disease management: a brief review and case studies. Plant Pathol 70:495–510 (2021).
      Ohkouchi T and Tsuji K, Basic technology and recent trends in agricultural formulation and application technology. J Pestic Sci 47:155–171 (2022).
      Wang R, Xu X, Shi X, Kou J, Song H, Liu Y et al., Promoting efficacy and environmental safety of pesticide synergists via non‐ionic gemini surfactants with short fluorocarbon chains. Molecules 27:6753 (2022).
      Bao Z, Wu Y, Song R, Gao Y, Zhang S, Zhao K et al., The simple strategy to improve pesticide bioavailability and minimize environmental risk by effective and ecofriendly surfactants. Sci Total Environ 851:158169 (2022).
      Li D, Wu X, Yu X, Huang Q and Tao L, Synergistic effect of non‐ionic surfactants Tween 80 and PEG6000 on cytotoxicity of insecticides. Environ Toxicol Pharmacol 39:677–682 (2015).
      Hu X, Gong H, Li Z, Ruane S, Liu H, Pambou E et al., What happens when pesticides are solubilized in nonionic surfactant micelles. J Colloid Interface Sci 541:175–182 (2019).
      Ahmady AR, Hosseinzadeh P, Solouk A, Akbari S, Szulc AM and Brycki BE, Cationic gemini surfactant properties, its potential as a promising bioapplication candidate, and strategies for improving its biocompatibility: a review. Adv Colloid Interface Sci 299:102581 (2022).
      Luo S, Chen Z, Dong Z, Fan Y, Chen Y, Liu B et al., Uniform spread of high‐speed drops on superhydrophobic surface by live‐oligomeric surfactant jamming. Adv Mater 31:1904475 (2019).
      Vereshchagin AN, Frolov NA, Egorova KS, Seitkalieva MM and Ananikov VP, Quaternary ammonium compounds (QACs) and ionic liquids (ILs) as biocides: from simple antiseptics to tunable antimicrobials. Int J Mol Sci 22:6793 (2021).
      Gonçalves RA, Holmberg K and Lindman B, Cationic surfactants: a review. J Mol Liq 375:121335 (2023).
      Kobisy AS, Nassar HN, Tawfik SM, Elshatoury EH and Aiad I, Mitigation of eco‐unfriendly and costly microbial induced corrosion using novel synthesized Schiff base cationic surfactants. J Chem Technol Biotechnol 96:941–952 (2021).
      Wojcieszak M, Syguda A, Lewandowska A, Marcinkowska A, Siwińska‐Ciesielczyk K, Wilkowska M et al., Synthesis and surface properties of piperidinium‐based herbicidal ionic liquids as a potential tool for weed control. J Agric Food Chem 71:4550–4560 (2023).
      Kaczmarek DK, Rzemieniecki T, Gwiazdowska D, Kleiber T, Praczyk T and Pernak J, Choline‐based ionic liquids as adjuvants in pesticide formulation. J Mol Liq 327:114792 (2021).
      Elmasry N, Nasr H and Harraz N, Insecticidal, acaricidal and biochemical evaluation of some synthetic azobenzene‐hydrazone derivatives with nano cationic adjuvant. Aust J Entomol 6:100–107 (2021).
      Marcinkowska K, Sobiech Ł, Kuliszewska E and Skrzypczak G, Effect of gemini surfactants on the glyphosate efficacy. Przemysl Chemiczny 93:911–913 (2014).
      Mirgorodskaya АB, Kushnazarova RА, Lukashenko SS, Nikitin EN, Sinyashin KO, Nesterova LM et al., Carbamate‐bearing surfactants as effective adjuvants promoted the penetration of the herbicide into the plant. Colloids Surf A 586:124252 (2020).
      Mirgorodskaya AB, Kushnazarova RA, Zakharova LY, Ulyanova AA, Litvinov DY, Blinkov AO et al., Enhanced herbicidal action of clopyralid in the form of a supramolecular complex with a gemini surfactant. Agronomy 13:973 (2023).
      Wojcieszak M, Krupa B, Syguda A, Walkiewicz F, Wilkowska M, Kozak M et al., Surface activity and phytotoxicity of morpholinium herbicidal ionic liquids. J Mol Liq 362:119750 (2022).
      Stachowiak W, Szumski R, Homa J, Woźniak‐Karczewska M, Parus A, Strzemiecka B et al., Transformation of iodosulfuron‐methyl into ionic liquids enables elimination of additional surfactants in commercial formulations of sulfonylureas. Molecules 26:4396 (2021).
      Syguda A, Wojcieszak M, Materna K, Woźniak‐Karczewska M, Parus A, Ławniczak Ł et al., Double‐action herbicidal ionic liquids based on dicamba esterquats with 4‐CPA, 2,4‐D, MCPA, MCPP, and clopyralid anions. ACS Sustainable Chem Eng 8:14584–14594 (2020).
      Simon‐Delso N, Amaral‐Rogers V, Belzunces LP, Bonmatin JM, Chagnon M, Downs C et al., Systemic insecticides (neonicotinoids and fipronil): trends, uses, mode of action and metabolites. Environ Sci Pollut Res 22:5–34 (2015).
      Tonietto BD, Laurentino AOM, Costa‐Valle MT, Cestonaro LV, Antunes BP, Sates C et al., Imidacloprid‐based commercial pesticide causes behavioral, biochemical, and hematological impairments in Wistar rats. Environ Toxicol Pharmacol 94:103924 (2022).
      Borsuah JF, Messer TL, Snow DD, Comfort SD and Mittelstet AR, Literature review: global neonicotinoid insecticide occurrence in aquatic environments. Water 12:3388 (2020).
      Mirgorodskaya AB, Kushnazarova RA, Lukashenko SS, Voloshina AD, Lenina OA, Zakharova LY et al., Carbamate‐bearing surfactants: Micellization, solubilization, and biological activity. J Mol Liq 269:203–210 (2018).
      Mirgorodskaya AB, Kushnazarova RA, Lukashenko SS and Zakharova LY, Self‐assembly of mixed systems based on nonionic and carbamate‐bearing cationic surfactants as a tool for fabrication of biocompatible nanocontainers. J Mol Liq 292:111407 (2019).
      Kushnazarova RA, Mirgorodskaya AB, Lukashenko SS, Voloshina AD, Sapunova AS, Nizameev IR et al., Novel cationic surfactants with cleavable carbamate fragment: tunable morphological behavior, solubilization of hydrophobic drugs and cellular uptake study. J Mol Liq 318:113894 (2020).
      Nasruddin A, Jumardi J and Melina M, Population dynamics of Trialeurodes vaporariorum (Westwood) (Hemiptera: Aleyrodidae) and its populations on different planting dates and host plant species. Ann Agric Sci 66:109–114 (2021).
      Darshanee HLC, Ren H, Ahmed N, Zhang Z‐F, Liu Y‐H and Liu T‐X, Volatile‐mediated attraction of greenhouse whitefly Trialeurodes vaporariorum to tomato and eggplant. Front Plant Sci 8:1285 (2017).
      Jones DR, Plant viruses transmitted by whiteflies. Eur J Plant Pathol 109:195–219 (2003).
      Fiallo‐Olivé E, Pan L‐L, Liu S‐S and Navas‐Castillo J, Transmission of begomoviruses and other whitefly‐borne viruses: dependence on the vector species. Phytopathology 110:10–17 (2020).
      Kushnazarova RA, Mirgorodskaya AB, Kuznetsov DM, Tyryshkina AA, Voloshina AD, Gumerova SK et al., Modulation of aggregation behavior, antimicrobial properties and catalytic activity of piperidinium surfactants by modifying their head group with a polar fragment. J Mol Liq 336:116318 (2021).
      IRAC, IRAC susceptibility test method 015 https://irac-online.org/methods/trialeurodes-vaporariorum-bemisia-tabaci-adult/ (accessed 1 December, 2023).
      Barman M, Samanta S, Thakur H, Chakraborty S, Samanta A, Ghosh A et al., Effect of neonicotinoids on bacterial symbionts and insecticide‐resistant gene in whitefly, Bemisia tabaci. Insects 12:742 (2021).
      Abbott WS, A method of computing the effectiveness of an insecticide. J Econ Entomol 18:265–267 (1925).
      Finney DJ, Probit Analysis. Cambridge University Press, New York (1980).
      Mǎgeruşan L, Pogǎcean F, Cozar B‐I, Tripon S‐C and Pruneanu S, Harnessing graphene‐modified electrode sensitivity for enhanced ciprofloxacin detection. Int J Mol Sci 25:3691 (2024).
      Šesták Z, Čatskỳ J and Jarvis PG, Plant Photosynthetic Production: Manual of Methods, W. Junk (1971).
      OECD, guidelines for the testing of chemicals, section 3: Environmental fate and behavior https://read.oecd-ilibrary.org/environment/test-no-301-ready-biodegradability_9789264070349-en (accessed 22 November, 2023).
      Mirgorodskaya AB, Kushnazarova RA, Sharonova NL, Rakhmaeva AM, Tyryshkina AA, Kuznetsov DM et al., New piperidinium surfactants with a benzyl fragment in the head group: aggregation properties and the possibility of using to control plant pathogens. Russ Chem Bull 71:1679–1686 (2022).
      Dolzhenko OV and Dolzhenko TV, Imidacloprid and technologies of its application for potato seed plantings protection against aphids. Agrochemistry 2:65–70 (2021).
      Confidor® 200 SC Insecticide, https://www.crop.bayer.com.au/products/insecticides/confidor‐200‐sc‐insecticide#tab‐1 (accessed 25 April, 2024).
      Papchenkova GA and Makrushin AV, Effect of the insecticide Tanrec® on reproduction and vital activity of Daphnia magna Straus in a 15‐day test. Inland Water Biol 6:344–350 (2013).
      Zhiltsova EP, Valeeva FG, Kuznetsov DM, Kushnazarova RA, Vasilieva EA, Mirgorodskaya AB et al., Alkaline hydrolysis of paraoxon in micellar solutions of carbamate surfactant. Russ J Gen Chem 94:386–394 (2024).
      Banno T, Kawada K and Matsumura S, Creation of novel green and sustainable gemini‐type cationics containing carbonate linkages. J Surfactants Deterg 13:387–398 (2010).
      Banno T, Toshima K, Kawada K and Matsumura S, Synthesis and properties of gemini‐type cationic surfactants containing carbonate linkages in the linker moiety directed toward green and sustainable chemistry. J Surfactanst Deterg 12:249–259 (2009).
      Wang Y, Jiang Y, Geng T, Ju H and Duan S, Synthesis, surface/interfacial properties, and biological activity of amide‐based Gemini cationic surfactants with hydroxyl in the spacer group. Colloids Surf. A 563:1–10 (2019).
      Guziałowska‐Tic J and Jan Tic W, Environmentally friendly paint and varnish additives based on isobutyrate aldehyde condensation products, ed. by Wzorek M, Królczyk G, and Król A. E3S Web Conf 19:02031 (2017).
      Žgajnar Gotvajn A and Zagorc‐Končan J, Laboratory simulation of biodegradation of chemicals in surface waters: closed bottle and respirometric test. Chemosphere 38:1339–1346 (1999).
      Iqbal N, Khan NA, Ferrante A, Trivellini A, Francini A and Khan MIR, Ethylene role in plant growth, development and senescence: interaction with other phytohormones. Front Plant Sci 8:475 (2017).
      Li P, Lu Y‐J, Chen H and Day B, The lifecycle of the plant immune system. CRC Crit Rev Plant Sci 39:72–100 (2020).
    • Contributed Indexing:
      Keywords: adjuvant; insecticide; surfactant; wetting; whitefly greenhouse
    • Accession Number:
      0 (Insecticides)
      0 (Surface-Active Agents)
      0 (Neonicotinoids)
      3BN7M937V8 (imidacloprid)
      0 (Nitro Compounds)
      0 (Carbamates)
      0 (Piperidines)
    • Publication Date:
      Date Created: 20240722 Date Completed: 20241007 Latest Revision: 20241007
    • Publication Date:
      20241007
    • Accession Number:
      10.1002/ps.8329
    • Accession Number:
      39034816