Abstract
Adjuvants such as surfactants improve pesticide efficiency by multiple mechanisms. In particular surfactants increase the foliar uptake of herbicides, growth regulators, and defoliants. Therefore, the choice of the adjuvant in an agrochemical formulation is crucial. Surfactants include anionic, nonionic, amphoteric and cationic surfactants. This review describes the role and properties of new adjuvants for agriculture. In particular adjuvants such as glyphosate formulations are modified to decrease ecotoxicity.
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References
Abribat B, Anderson T, Oester D (2007) Alkoxylated polyglycosides, next generation glyphosate potentiators. In: Gaskin RE (ed) Proceedings of the 8th international symposium on adjuvants for agrochemicals, ISAA, Christchurch
Aladesanwa RD, Oladimeji MO (2005) Optimizing herbicidal efficacy of glyphosate isopropylamine salt through ammonium sulphate as surfactant in oil palm (Elaeis guineensis) plantation in a rainforest area of Nigeria. Crop Prot 24:1068–1073
Alberts E, Kalverboer AF, Hopkins B (1983) Mother infant dialog in the first days of life an observational study during breast-feeding. J Child Psychol Psychiatry 24:145–161
Anderson TH (2010) Sulphated glycerine, a new sequestrant and adjuvant for herbicide sprays. In: Baur P, Bonnet M (eds) Proceedings of the 9th international symposium on adjuvants for agrochemicals, Dynevo, Leverkusen, pp 301–306
Annual Book of ASTM Standards (2006) Volume 11.04, E 1519-06a, ASTM International, West Conshohocken. www.astm.org
Badawy MEI, Rabea EI, Rogge TM, Stevens CV, Smagghe G, Steurbaut W, Höfte M (2004) Synthesis and fungicidal activity of new N, O-acyl chitosan derivatives. Biomacromolecules 5:589–595
Baker EA, Hayes AL, Butler RC (1992) Physicochemical properties of agrochemicals: their effects on foliar penetration. Pestic Sci 34:167–182
Banduhn MC, Frazier HW (1978) G 3780A surfactant: biodegradation in nature waters. report no. MSL-0488. Monsanto Company, St. Louis
Bauer H, Schönherr J (1992) Determination of mobilities of organic compounds in plant cuticles and correlation with molar volumes. Pestic Sci 35:1–11
Bean M, Cutler J (2000) Agrochemical composition. EP Patent 1006792
Becker M, Kerstiens G, Schönherr J (1986) Water permeability of plant cuticles: permeance, diffusion and partition coefficients. Trees 1:54–60
Behler A, Clasen F (2006) Method for the alkoxylation of alkyl/alkylene polyglycosides. EP Patent 1716163
Beyers SW (1995) Acute toxicity of Rodeo® herbicide to Rio Grande silvery minnow as estimated by surrogate species: plains minnow and fathead minnow. Arch Environ Contam Toxicol 29:24–26
Blair AM (1975) The addition of ammonium salt or phosphate ester to herbicides to control Agropyron repens (L) Beaux. Weed Res 15:101–105
Bromilow RH, Chamberlain K (2000) The herbicide glyphosate and related molecules: physicochemical and structural factors determining their mobility in phloem. Pest Manag Sci 56:368–373
Bromilow RH, Chamberlain K, Evans A (1990) Physicochemical aspects of phloem translocation of herbicides. Weed Sci 38:305–314
Buchholz A, Peter B, Schönherr J (1998) Differences among plant species in cuticular permeabilities and solute mobilities are not caused by differential size selectivities. Planta 206:322–328
Buhler DD, Burnside OC (1983a) Effect of water quality, carrier volume, and acid on glyphosate phytotoxicity. Weed Sci 31:163–169
Buhler DD, Burnside OC (1983b) Effect of spray components on glyphosate toxicity to annual grasses. Weed Sci 35:124–130
Buhler DD, Burnside OC (1987) Effects of application variables on glyphosate phytotoxicity. Weed Technol 1:14–17
Burghardt M, Schreiber L, Riederer M (1998) Enhancement of the diffusion of active ingredients in barley leaf cuticular wax by monodisperse alcohol ethoxylates. J Agric Food Chem 46:1593–1602
Burval J, Chan JH (1995) Liquid phytoactive compositions. US Patent 5 468 718
Campbell P (2002) Alternatives to nonylphenol ethoxylates, Review of toxicity, biodegradation & technical-economic aspects. In: ToxEcology environmental consulting, Report for Environment Canada, Vancouver
Cano ML, Dorn PB (1996) Sorption of two model alcohol ethoxylate surfactants to sediments. Chemosphere 33:981–994
Casely JC, Coupland D (1985) Environmental and plant factors affecting glyphosate uptake, movement and activity. In: Grossbard E, Atkinson D (eds) The herbicide glyphosate. Butterworth and Co, London, pp 92–123
Chefetz B (2003) Sorption of phenanthrene and atrazine by plant cuticular fractions. Environ Toxicol Chem 22:2492–2498
Chellat F, Tabrizian M, Dumitriu S, Chornet E, Rivard CH, Yahia LH (2000) Study of biodegradation behavior of chitosan-xanthan microspheres in simulated physiological media. J Biomed Mater Res 53:592–599
Chen B, Li Y (2007) Sorption of 1-naphthol by plant cuticular fractions. J Environ Sci 19:1214–1220
Chen F, Wang Y, Zheng F, Wu Y, Liang W (2000) Studies on cloud point of agrochemical microemulsions. Colloids Surf A 175:257–262
Chen B, Li Y, Guo Y, Zhu L, Schnoor JL (2008) Role of the extractable lipids and polymeric lipids in sorption of organic contaminants onto plant cuticles. Environ Sci Technol 42:1517–1523
Contardo-Jara V, Klingelmann E, Wiegand C (2009) Bioaccumulation of glyphosate and its formulation Roundup® Ultra in Lumbriculus variegatus and its effects on biotransformation and antioxidant enzymes. Environ Pollut 157:57–63
Cordiner JL (2004) Challenges for the PSE community in formulations. Comput Chem Eng 29:83–92
Coret J, Chamel A (1995) Effects and possible mode of action of some nonionic surfactants on the diffusion of glyphosate and chlorotoluron across isolated plant cuticles. Pestic Sci 43:163–166
Coupland D (1988) Factors affecting the phloem translocation of foliage applied herbicides. In: Aitken RK, Clifford DR (eds) British plant growth regulation 18. British Plant Growth Regulation Group Monograph, pp 85–112
Crafts AS (1960) Evidence for hydrolysis of esters of 2,4-D during absorption by plants. Weeds 8:19–25
Cranmer JR, Linscott DL (1990) Droplet makeup and the effect on phytotoxicity of glyphosate in velvetleaf (Abutilon theophrasti). Weed Sci 38:406–410
Dayan FE, Cantrell CL, Duke SO (2009) Natural products in crop protection. Bioorg Med Chem 17:4022–4034
De Ruiter H, Uffing AJM, Meinen E, Prins A (1990) Influence of surfactants and plant species on leaf retention of spray solutions. Weed Sci 38:567–572
De Ruiter H, Straatman K, Meinen E (1993) The influence of a fatty amine surfactant on foliar absorption and translocation of the trolamine salt and iso-octyl ester of 2,4-D. Pestic Sci 38:145–154
De Ruiter H, Uffing AJM, Meinen E (1996) Influence of surfactants and ammonium sulfate on glyphosate phytotoxicity to quackgrass (Elytigia repens). Weed Technol 10:803–808
Denis MH, Delrot S (1993) Carrier-mediated uptake of glyphosate in broad bean (Vicia faba) via a phosphate transporter. Physiol Plantar 87:569–575
Denis MH, Delrot S (1997) Effects of salt and surfactants on foliar uptake and long distance transport of glyphosate. Plant Physiol Biochem 35:291–301
Devine MD, Hall LM (1990) Implications of sucrose transport mechanisms for the translocation of herbicides. Weed Sci 38:299–304
Dodds EC, Lawson W (1938) Molecular structure in relation to estrogenic activity: compounds without a phenanthrene nucleus. Proc R Soc Lond B Biol Sci 125:222–232
Duncan Yerkes CN, Weller SC (1996) Diluent volume influences susceptibility of field bindweed (Convolvulus arvensis) biotypes to glyphosate. Weed Technol 10:565–569
Edser C (2007) Multifaceted role for surfactants in agrochemicals. Focus Surfact 3:1–2
Feng PCC, Ryerse JS, Sammons RD (1998) Correlation of leaf damage with uptake and translocation of glyphosate in velvetleaf (Abutilon theophrasti). Weed Technol 12:300–307
Feng PCC, Ryerse JS, Jones CR, Sammons RD (1999) Analysis of surfactant leaf damage using microscopy and its relation to glyphosate or deuterium oxide uptake in velvetleaf (Abutilon theophrasti). Pest Sci 55:385–386
Feng PCC, Chiu T, Sammons RD, Ryerse JS (2003a) Droplet size affects glyphosate retention, absorption and translocation in corn. Weed Sci 51:443–448
Feng PCC, Chiu T, Sammons RD (2003b) Glyphosate efficacy is contributed by its tissue concentration and sensitivity in velvetleaf (Abutilon theophrasti). Pest Biochem Physiol 77:83–91
Fernández Cirelli A, Ojeda C, Castro MJL, Salgot M (2008) Surfactants in sludge- amended agricultural soils. A review. Environ Chem Lett 6:135–148
Folmar LC, Sanders OH, Julin AM (1979) Toxicity of the herbicide glyphosate and several of its formulations to fish and aquatic invertebrates. Arch Environ Contam Toxicol 8:269–278
Forgiarini A, Esquena J, Gonzalez C, Solans C (2001) Formation of nano-emulsions by low-energy emulsification methods at constant temperature. Langmuir 17:2076–2083
Forster WA, Zabkiewicz JA, Riederer M (2004) Mechanisms of cuticular uptake of xenobiotics into living plants: 1. Influence of xenobiotic dose on the uptake of three model compounds, applied in the absence and presence of surfactants into Chenopodium album, Hedera helix and Stephanotis floribunda leaves. Pest Manage Sci 60:1105–1113
Foy CL (1987) Adjuvants: terminology, classification, and mode of action. In: Chow PNP, Grant CA, Hinshalwood AM, Simundson E (eds) Adjuvants and agrochemicals. CRC Press, Boca Raton, pp 1–15
Foy CL (1989) Adjuvants for agrochemicals: introduction, historical overview and future outlook. In: Chow PNP, Grant CA, Hinshalwood AM, Simundsson E (eds) Adjuvants and agrochemicals: II recent development, application, and bibliography of agro adjuvants. CRC Press, Boca Raton, pp 2–9
Franz JE, Mao MK, Sikorski JA (1997) Glyphosate: a unique global herbicide. In: ACS monograph, vol. 189, American Chemical Society, Washington, DC, pp 163–175
Gardner SC, Grue CE (1996) Effects of rodeo® and garlon 3A on nontarget wetland species in central Washington. Environ Toxicol Chem 15:441–451
Garst R (1997) New solutions for agricultural applications. In: Hill K, Rybinski W, Stoll G (eds) Alkyl polyglycosides. VCH, Weinheim, pp 131–137
Gednalske JV, Herzfeld RW (1994) Homogenous herbicidal adjuvant blend comprising glyphosate ammonium sulfate and alkyl polysaccharide. US Patent 5 356 861
Geiger DR, Bestman HD (1990) Self-limitation of herbicide mobility by phytotoxic action. Weed Sci 38:324–329
Geiger DR, Shieh WJ, Fuchs MA (1999) Causes of selflimited translocation of glyphosate in Beta vulgaris plants. Pest Biochem Physiol 64:124–133
Giesy JP, Dobson S, Solomon KR (2000) Ecotoxicological risk assessment for Roundup® herbicide. Rev Environ Contam Toxicol 167:35–120
Giger W, Brunner PH, Schaffner C (1984) 4-Nonylphenol in sewage-sludge: accumulation of toxic metabolites from nonionic surfactants. Science 225:623–625
Goldsborough LG, Brown DJ (1993) Dissipation of glyphosate and aminomethylphosphonic acid in water and sediments of boreal forest ponds. Environ Toxicol Chem 12:1139–1147
Gougler JA, Geiger DR (1984) Carbon partitioning and herbicide translocation in glyphosate treated sugar beet (Beta vulgaris). Weed Sci 32:546–551
Green JM, Beestman GB (2007) Recently patented and commercialized formulation and adjuvant technology. Crop Prot 26:320–327
Harring T, Streibig JC, Husted S (1998) Accumulation of shikimic acid: a technique for screening glyphosate efficacy. J Agric Food Chem 46:4406–4412
Hartley GS, Brunskill RT (1958) Reflection of water droplets from surfaces. In: Danielli JF, Parkhurst KGA, Riddiford AC (eds) Surface phenomena in chemistry and biology. Pergamon Press, New York, pp 214–223
Hartzler B (2001) Glyphosate- a review. Iowa State University, Ames, Iowa
Heinemann A (2010) Megatrends in agriculture. In: Proceedings of the 8th international symposium on adjuvants for agrochemicals. ISAA Society, Freising, pp 19–20
Hejazi R, Amiji M (2003) Chitosan-based gastrointestinal delivery systems. J Control Release 89:151–165
Heldt N, Zhao J, Friberg S, Zhang Z, Slack G, Li Y (2000) Controlling the size of vesicles prepared from egg lecithin using a hydrotrope. Tetrahedron 56:6985–6990
Henry CJ, Higgins KF, Buhl KJ (1994) Acute toxicity and hazard assessment of Rodeo, X-77 Spreader, and Chem-Trol to aquatic invertebrates. Arch Environ Contam Toxicol 27:392–399
Hess FD, Foy CL (2000) Interaction of surfactants with plant cuticles. Weed Technol 14:807–813
Hochberg EG (1996) The market for agricultural pesticide inert ingredients and adjuvants. In: Foy CL, Pritchard DW (eds) Pesticide formulation and adjuvant technology. CRC Press, Boca Raton, pp 203–208
Holden WTC (1992) Future formulation trends – the likely impact of regulatory and legislative pressures. In: Brighton crop protection conference, vol. 11, BCPC, Brighton, pp 313–320
Holloway PJ (1993) Structure and chemistry of plant cuticles. Pestic Sci 37:203–232
Jeffree C (1996) Cuticles: an integrated functional approach. In: Kerstiens G (ed) Plant. BIOS scientific, Oxford
Jobling S, Sheahan D, Osborne JA, Matthiessen P, Sumpter JP (1996) Inhibition of testicular growth in rainbow trout (Oncorhynchus mykiss) exposed to estrogenic alkylphenolic chemicals. Environ Toxicol Chem 15:194–202
Jordan TN (1981) Effects of diluent volumes and surfactant on the phytotoxicity of glyphosate to bermuda grass (Cynodon dactylon). Weed Sci 29:79–83
Khot LR, Sankaran S, Maja JM, Ehsani R, Schuster EW (2012) Applications of nanomaterials in agricultural production and crop protection: a review. Crop Prot 35:64–70
Kim Y-S, Katase T, Sekine S, Inoue T, Makino M, Uchiyama T, Fujimoto Y, Yamashita N (2004) Variation in estrogenic activity among fractions of a commercial nonylphenol by high performance liquid chromatography. Chemosphere 54:1127–1134
Kindall HW, Pimentel D (1994) Constraints on the expansion of the global food supply. Ambio 23:198–205
Kinnberg K, Korsgaard B, Bjerregaard P, Jespersen A (2000) Effects of nonylphenol and 17 beta-estradiol on vitellogenin synthesis and testis morphology in male platyfish Xiphophorus maculatus. J Exp Biol 203:171–181
Kirkwood RC (1999) Recent developments in our understanding of the plant cuticle as a barrier to the foliar uptake of pesticides. Pestic Sci 55:69–77
Knowles A (2008) Recent developments of safer formulations of agrochemicals. Environmentalist 28:35–44
Krogh PH, Holmstrup M, Petersen SO, Jensen J (1997) Ecotoxicological assessment of sewage sludge in agricultural soil. In: Danish ministry for the environment, The Environmental Protection Agency, working report No. 69
Krogh KA, Halling-Sørensen B, Mogensen BB, Vejrup KV (2003) Environmental properties and effects of nonionic surfactant adjuvants in pesticides: a review. Chemosphere 50:871–901
Kumar MNVR, Muzzarelli RA, Muzzarelli C, Sashiwa H, Domb AJ (2004) Chitosan chemistry and pharmaceutical perspectives. Chem Rev 104:6017–6084
Lao SB, Zhang ZX, Xu HH, Jiang GB (2010) Novel amphiphilic chitosan derivatives: synthesis, characterization and micellar solubilization of rotenone. Carbohyd Polym 82:1136–1142
Lasic DD (1993) Liposomes from physics to applications. Elsevier, Amsterdam, pp 507–516
Laws SC, Carey SA, Ferrell JM, Bodman GJ, Cooper RL (2000) Estrogenic activity of octylphenol, nonylphenol, bisphenol A and methoxychlor in rats. Toxicol Sci 54:154–167
Lee PC, Lee W (1996) In vivo estrogenic action of nonylphenol in immature female rats. Bull Environ Contam Toxicol 57:341–348
Lee GWJ, Tadros TF (1982) Formation and stability of emulsions produced by dilution of emulsifiable concentrates. Part I. An investigation of the dispersion on dilution of emulsifiable concentrates containing cationic and non-ionic surfactants. Colloids Surf 5:105–115
Lee JF, Liao PM, Kuo CC, Yang HT, Chiou CT (2000) Influence of a nonionic surfactant (Trion X-100) on contaminant distribution between water and several soil solids. J Colloid Interface Sci 229:445–452
Lee HJ, Chattopadhyay S, Gong EY, Ahn RS, Lee K (2003) Antiandrogenic effects of bisphenol a and nonylphenol on the function of androgen receptor. Toxicol Sci 75:40–46
Lee JF, Hsu MH, Chao HP, Huang HC, Wang SP (2004) The effect of surfactants on the distribution of organic compounds in the soil solid/water system. J Hazard Mater 114:123–130
Li Y, Chen B (2009) Phenanthrene sorption by fruit cuticles and potato periderm with different compositional characteristics. J Agric Food Chem 57:637–644
Lindman B, Danielson I (1981) The definition of microemulsion. Colloid Surf 3:391–392
Liu SH, Campbell RA, Studens JA, Wagner RG (1996) Absorption and translocation of glyphosate in aspen (Populus tremuloides Michx.) as influenced by droplet size, droplet number, and herbicide concentration. Weed Sci 44:482–488
Mainx HG, Hofer P (2009) Alkylene oxide adducts of oligosaccharides. Patent WO 2009080215
Malec, AD, Figley, TM, Turpin, KL (2009) Ultra-high loading glyphosate concentrate. US Patent 20090318294
Marc J, Mulner-Lorillon O, Boulben S, Hureau D, Durand G, Belle R (2002) Pesticide Roundup® provokes cell division dysfunction at the level of CDK1/cyclin B activation. Chem Res Toxicol 15:326–331
Martinez TT, Brown K (1991) Oral and pulmonary toxicology of the surfactant used in Roundup® herbicide. Proc West Pharmacol Soc 34:43–46
Marvel JT, Brightwell BB, Suba L (1974) G 3780A surfactant: biodegradation, plant uptake, and 14C-distribution. In: Report 321, Monsanto Company, St. Louis
May OL, Culpepper AS, Cerny RE, Coots CB, Corkern CB, Cothren JT, Croon KA, Ferreira KL, Hart JL, Hayes RM, Huber SA, Martens AB, McCloskey WB, Oppenhuizen ME, Patterson MG, Reynolds DB, Shappley ZW, Subramani J, Witten TK, York AC, Mullinix BG (2002) Transgenic cotton with improved resistance to glyphosate herbicide. Crop Sci 44:234–240
McAllister RS, Haderlie LC (1985) Translocation of 14C-glyphosate and 14C-CO2-labeled photoassimilates in Canada thistle (Cirsium arvense). Weed Sci 33:153–159
Mercer GN (2007) A simple diffusion model of the effect of droplet size and spread. Area on foliar uptake of hydrophilic compounds. Pest Biochem Physiol 88:128–133
Minanaperez M, Gracia A, Lachaise J, Salager JL (1995) Solubilization of polar oils with extended surfactants. Colloid Surf A Physicochem Eng Asp 100:217–224
Morin F, Vera V, Nurit F, Tissut M, Marigo G (1997) Glyphosate uptake in Catharanthus roseus cells: role of a phosphate transporter. Pest Biochem Physiol 58:13–22
Muzik TJ (1976) Influence of environmental factors on toxicity to plants. In: Audus LJ (ed) Herbicides: physiology, biochemistry, ecology, 2nd edn. Academic, London, pp 203–247
Nadler-Hassar T, Goldshmidt A, Rubin B, Wolf S (2004) Glyphosate inhibits the translocation of green fluorescent protein and sucrose from a transgenic tobacco host to Cuscuta campestris Yunk. Planta 219:790–796
Nalewaja JD, Devilliers B, Matysiak R (1996) Surfactant and salt affect glyphosate retention and absorption. Weed Res 36:241–247
Nickel D, Föster T, von Rybinski W (1996) Physicochemical properties of alkyl polyglycosides. In: Hill K, Rybinski W, Stoll G (eds) Alkyl polyglucosides. VCH, Weinheim, pp 39–69
Odum J, Lefevre PA, Tittensor S, Paton D, Routledge EJ, Beresford NA, Sumpter JP, Ashby J (1997) The rodent uterotrophic assay: critical protocol features, studies with nonyl phenols, and comparison with a yeast estrogenicity assay. Regul Toxicol Pharmacol 25:176–188
Oparka KJ, Roberts AG (2001) Plasmodesmata. A not so open-and-shut case. Plant Physiol 125:123–126
Paganelli A, Gnazzo V, Acosta H, Lopez SL, Carrasco A (2010) Glyphosate-based herbicides produce teretogenic effects on vertebrates by impairing retinoic acid signaling. Chem Res Toxicol 23:1586–1595
Paveglio PL, Kilbride KM, Grue CE, Siemenstad CA, Fresh KL (1996) Use of Rodeo and X-77 spreader to control smooth cordgrass (Spartina alterniflora) in a southwestern Washington estuary: 1 environmental fate. Environ Toxicol Chem 15:961–968
Peixoto F (2005) Comparative effects of the Roundup® and glyphosate on mitochondrial oxidative phosphorylation. Chemosphere 61:1115–1122
Perkins MC, Roberts CJ, Briggs D, Davies MC, Friedmann A, Hart C, Bell G (2005) Macro and microthermal analysis of plant wax/surfactant interactions: plasticizing effects of two alcohol ethoxylated surfactants on an isolated cuticular wax and leaf model. Appl Surf Sci 243:158–165
Petracek PD, Fader RG, Knoche M, Bukovac MJ (1998) Surfactant-enhanced penetration of benzyladenine through isolated tomato fruit cuticular membranes. J Agric Food Chem 46:2346–2352
Pimentel D (1995) Amounts of pesticides reaching the target pests: environmental impacts and ethics. J Agric Environ Ethics 8:17–29
Pimentel D (1997) Techniques for reducing pesticide use. Wiley, New York
Pompeo MP, Mainx HG, Eskuchen R, Rosessing M, Abribat B (2005) APG Granules containing agrochemical active ingredients. US Patent 0,009,707
Pons M, Estelrich J (1996) Liposomes as an agrochemical tool: optimization of their production. Ind Crop Prod 5:203–208
Popp C, Burghardt M, Friedmann A, Riederer M (2005) Characterization of hydrophilic and lipophilic pathways of Hedera helix L. cuticular membranes: permeation of water and uncharged organic compounds. J Exp Bot 56:2797–2806
Price CE (1976) Penetration and translocation of herbicides and fungicides in plants. In: McFarlane NR (ed) Herbicides and fungicides-factors affecting their activity, vol 29, The chemical society special publication. Chemical Society, London, pp 42–66
Price CE (1983) The effect of environment on foliage uptake and translocation of herbicides. In: A.o.A. Biologists (ed) Aspects of applied biology 4: influence of environmental factors on herbicide performance and crop and weed biology, vol. 4, The Association of Applied Biologists, Warwick, pp 157–169
Prince LM (1977) Microemulsion. Academic, London
Rabea EI, Badawy MEI, Rogge TM, Stevens CV, Höfte M, Steurbaut W, Smagghe G (2005) Insecticidal and fungicidal activity of new synthesized chitosan derivatives. Pest Manag Sci 61:951–960
Ramsey RJL, Stephenson GR, Hall JC (2005) A review of effects of humidity, humectants, and surfactants composition on the absorption and efficacy of highly water-soluble herbicides. Pest Biochem Physiol 82:162–175
Reynhardt EC, Riederer M (1994) Structures and molecular dynamics of plant waxes. II Cuticular waxes from leaves of Fagus sylvatica L. and Hordeum vulgare L. Eur Biophys J 23:59–70
Richard EP Jr, Slife FW (1979) In vivo and in vitro characterization of the foliar entry of glyphosate in hemp dogbane (Apocynum cannabinum). Weed Sci 27:426–433
Riechers DE (1992) Surfactant effects on the plasma membrane as a mode of action in promoting glyphosate phytotoxicity. M.Sc. thesis, University of Illinois, Urbana-Champaign
Riechers DE, Wax LM, Liebl RA, Bush DR (1994) Surfactant-increased glyphosate uptake into plasma membrane vesicles isolated from common lambsquarters leaves. Plant Physiol 105:1419–1425
Riechers DE, Wax LM, Liebl RA, Bullock DG (1995) Surfactant effects on glyphosate efficacy. Weed Technol 9:281–285
Riederer M, Markstädter C (1996) Cuticular waxes: a critical assessment of current knowledge. In: Kerstiens G (ed) Plant cuticles – an integrated functional approach. Bios Scientific, Oxford, pp 189–200
Riederer M, Schreiber L (2001) Protecting against water loss: analysis of the barrier properties of plant cuticles. J Exp Bot 52:2023–2032
Risbud MV, Bhonda RR (2000) Polyacrylamide-chitosan hydrogels: in vitro biocompatibility and sustained antibiotic release studies. Drug Deliv 7:69–75
Roberts J (2010) Helena Chemical Company, Presentation to EPA
Ryerse JS, Feng PCC, Sammons RD (2001) Endogenous fluorescence identifies dead cells in plants. Microsc Today 1:22–24
Saito H, Shinoda K (1967) The solubilization of hydrocarbons in aqueous solutions of nonionic surfactants. J Colloid Interface Sci 24:10–15
Santier S, Chamel A (1998) Reassessment of the role of cuticular waxes in the transfer of organic molecules through plant cuticles. Plant Physiol Biochem 36:225–231
Satchivi NM, Stoller EW, Wax LM, Briskin DP (2000a) A nonlinear dynamic simulation model for xenobiotic transport and whole plant allocation following foliar application I. Conceptual foundation for model development. Pestic Biochem Physiol 68:67–84
Satchivi NM, Stoller EW, Wax LM, Briskin DP (2000b) A nonlinear dynamic simulation model for xenobiotic transport and whole plant allocation following foliar application II. Model validation. Pestic Biochem Physiol 68:85–95
Satchivi NM, Stoller EW, Wax LM, Briskin DP (2001) A nonlinear dynamic simulation model for xenobiotic transport and whole plant allocation following foliar application III. Influence of chemical properties, plant characteristics, and environmental parameters on xenobiotic absorption and translocation. Pestic Biochem Physiol 71:77–87
Satchivi NM, Stoller EW, Wax LM, Briskin DP (2006) A nonlinear, dynamic, simulation model for transport, and whole plant allocation of systemic xenobiotics following foliar application IV. Physiochemical properties requirements for optimum absorption and translocation. Pestic Biochem Physiol 84:83–97
Schönherr J (2000) Calcium chloride penetrates plant cuticles via aqueous pores. Planta 212:112–118
Schönherr J (2002) A mechanistic analysis of penetration of glyphosate salts across astomatous cuticular membrane. Pest Manag Sci 58:343–351
Schönherr J, Schreiber L (2004) Size selectivity of aqueous pores in astomatous cuticular membranes isolated from Populus canescens (Aiton) Sm. leaves. Planta 219:405–411
Schönherr J, Baur P, Buchholz A (1999) Modelling foliar penetration: its role in optimising pesticide delivery. In: Brooks GT, Roberst TR (eds) Pesticide chemistry and bioscience. Royal Society of Chemistry, Cambridge, pp 134–151
Schönherr J, Baur P, Uhlig BA (2000) Rates of cuticular penetration of 1-naphthylacetic acid (NAA) as affected by adjuvants, temperature, humidity and water quality. Plant Growth Regul 31:61–74
Schreiber L (1995) A mechanistic approach towards surfactant/wax interactions: effects of octaethyleneglycolmonododecylether on sorption and diffusion of organic chemicals in reconstituted cuticular wax of barley leaves. Pestic Sci 45:1–11
Schreiber L (2006) Review of sorption and diffusion of lipophilic molecules in cuticular waxes and the effects of accelerators on the solute mobilities. J Exp Bot 57:2515–2523
Servizi JA, Gordon RW, Martens DW (1987) Acute toxicity of Garlon 4 and Roundup® herbicides to Salmon, Daphnia, and trout. Bull Environ Contam Toxicol 39:15–22
Sharma SD, Kirkwood RC, Whateley T (1996) Effect of nonionic nonylphenol surfactants on surface physiological properties, uptake and distribution of asulam and diflufenican. Weed Res 36:227–239
Sherrick SL, Holt HA, Hess FD (1986) Absorption and translocation of MON 0818 adjuvant in field bindweed (Convolvulus amcnsis). Weed Sci 34:817–823
Soares A, Vijayram IA, Guieysse B, Murto M, Guieysse B, Mattiasson B (2005) Degradation of non-ionic surfactants under anaerobic conditions. In: Rittmann BE, van Loosdrecht MCM (eds) Third IWA leading-edge conference on water and wastewater treatment technologies. IWA Publishing, Sapporo
Solel Z, Edgington LV (1973) Transcuticular movement of fungicides. Phytopathology 63:505–510
Soto AM, Justicia H, Wray JW, Sonnenschein C (1991) P-Nonylphenol: an estrogenic xenobiotic released from “modified” polystyrene. Environ Health Perspect 92:167–173
Stephenson DO, Patterson MG, Faircloth WH, Lunsford JN (2004) Weed management with fomesafen preemergence in glyphosate-resistant cotton. Weed Technol 18:680–686
Stevens PJG, Bukovac MJ (1987) Studies on octylphenoxy surfactants. Part 1: effects of oxyethylene content on properties of potential relevance to foliar absorption. Pestic Sci 20:9–35
Stevens PJG, Baker EA, Anderson NH (1988) Factors affecting the foliar absorption and redistribution of pesticides. 2. Physicochemical properties of the active ingredient and the role of surfactant. Pestic Sci 24:31–53
Stewart WN (1993) Paleobotany and the evolution of plants, Secondth edn. Cambridge University Press, New York, 405
Stock D, Holloway PJ (1993) Possible mechanisms for surfactant-induced foliar uptake of agrochemicals. Pestic Sci 38:165–177
Stock D, Edgerton BM, Gaskin RE, Holloway PJ (1992) Surfactant enhanced foliar uptake of some organic compounds: interactions with two model polyoxyethylene aliphatic alcohols. Pestic Sci 34:233–242
Stock D, Holloway PJ, Grayson BT, Whitehouse P (1993) Development of a predictive uptake model to rationalise selection of polyoxyethylene surfactant adjuvants for foliage applied agrochemicals. Pestic Sci 37:233–245
Strey R (1996) Water – nonionic surfactant – systems, and the effect of additives. Berich Bunsen Gesell Phys Chem Chem Phys 100:182–189
Tabata A, Kashiwada S, Ohnishi Y, Ishikawa H, Miyamoto N, Itoh M, Magara Y (2001) Estrogenic influences of estradiol-17 beta, p-nonylphenol and bis-phenol-A on Japanese Medaka (Oryzias latipes) at detected environmental concentrations. Water Sci Technol 43:109–116
Tabira Y, Nakai M, Asai D, Yakabe Y, Tahara Y, Shinmyozu T, Noguchi M, Takatsuki M, Shimohigashi Y (1999) Structural requirements of para-alkylphenols to bind to estrogen receptor. Eur J Biochem 262:240–245
Tadros TF (1994) Surfactants in agrochemicals. Marcel Dekker, New York
Tadros TF (2005) Applications of surfactants in agrochemicals. In: Applied surfactants: principles and application. Wiley-VCH, Weinheim, pp 503–592
Tamura H, Knoche M, Bukovac MJ (2001) Evidence for surfactant solubilization of plant epicuticular wax. J Agric Food Chem 48:1809–1816
Thomas BA, Spicer RA (1987) The evolution and paleobiology of land plants, vol 2, Ecology, phytogeography and physiology series. Croom Helm, London, pp 309
Tice CM (2001) Selecting the right compounds for screening: does Lipinski’s rule of 5 for pharmaceuticals apply to agrochemicals. Pest Manag Sci 57:3–16
Tilman D, Cassman KG, Matson PA, Naylor R, Polasky S (2002) Agricultural sustainability and intensive production practices. Nature 418:671–677
Tominack RL (2000) Herbicide formulations. J Toxicol Clin Toxicol 38:129–135
Trapp S (2004) Plant uptake and transport models for neutral and ionic chemicals. Environ Sci Pollut Res 11:33–39
Tsui MTK, Chu LM (2003) Aquatic toxicity of glyphosate-based formulations: comparison between different organisms and the effects of environmental factors. Chemosphere 52:1189–1197
Tu M, Hurd C, Randall JM (2003) Weed control methods handbook, The Nature Conservancy, Utah State University, Utah
Urano K, Saito M, Murata C (1984) Adsorption of surfactants on sediments. Chemosphere 12:293–300
van Ginkel CG, Stroo CA, Kroon AGM (1993) Biodegradability of ethoxylated fatty amines: detoxification through a central fission of these surfactants. Sci Total Environ 134:689–697
Wade BR, Riechers DE, Libel RA, Wax LM (1993) The plasma membrane as a barrier to herbicide penetration and site for adjuvant action. Pestic Sci 37:195–202
Wan Kim T, Amrhein N (1995) Glyphosate toxicity: long-term analysis of shikimic acid accumulation and chlorophyll degradation in tomato plants. Kor J Weed Sci 15:141–147
Wan MT, Watts RG, Moul DJ (1989) Effects of different dilution water types on the acute toxicity to juvenile Pacific salmon and rainbow trout of glyphosate and its formulated products. Bull Environ Contam Toxicol 43:378–385
Wang CJ, Liu ZQ (2007) Foliar uptake of pesticides – present status and future challenge. Pest Biochem and Physiol 87:1–8
Wang L, Li X, Zhang G, Dong J, Eastoe J (2007) Oil-in-water nanoemulsions for pesticide formulations. J Colloid Interface Sci 314:230–235
White R, Jobling S, Hoare SA, Sumpter JP, Parker MG (1994) Environmentally persistent alkylphenolic compounds are estrogenic. Endocrinology 135:175–182
Williams GM, Kroes R, Munro IC (2000) Safety evaluation and risk assessment of the herbicide Roundup® and its active ingredient, glyphosate, for humans. Regul Toxicol Pharmacol 31:117–165
Wills GD, McWhorter CG (1988) Absorption and translocation of herbicides effect of environment, adjuvants, and inorganic salts, pesticide formulations. In: Chapter 8, ACS symposium series, Vol 371, American Chemical Society, Washington, pp 90–101
Woodburn A (2000) Glyphosate: production, pricing and use worldwide. Pest Manage Sci 56:309–312
Wyrill JB, Burnside OC (1976) Absorption, translocation, and metabolism of 2,4-D and glyphosate in common milkweed and hemp dogbane. Weed Sci 24:557–566
Yoshihara K, Ohshima H, Momozawa N, Sakai H, Abe M (1995) Binding constants of symmetric or antisymmetric electrolytes and aggregation numbers of oil-in-water type microemulsions with a nonionic surfactant. Langmuir 11:2979–2984
Zabkiewicz JA (2000) Adjuvants and herbicidal efficacy – present status and future prospects. Weed Res 40:139–149
Zabkiewicz JA (2003) Foliar interactions and uptake of agrichemical formulations – present limits and future potential. In: Voss G, Ramos G (eds) Chemistry of crop protection. Wiley VCH, Weinheim, pp 237–251
Zabkiewicz JA (2007) Spray formulation efficacy – holistic and futuristic perspectives. Crop Prot 26:312–319
Zhang C, Ping QN, Zhang H, Shen J (2003) Preparation of N-alkyl-O-sulfate chitosan derivatives and micellar solubilization of taxol. Carbohyd Polym 54:137–141
Zhang C, Qu GW, Sun YJ, Wu XL, Yao Z, Guo QL, Ding Q, Yuan S, Shen Z, Ping Q, Zhou H (2008) Pharmacokinetics, biodistribution, efficacy and safety of N-octyl-O-sulphate chitosan micelles loaded with paclitaxel. Biomaterials 29:1233–1241
Zhu L, Chen B, Tao S (2004) Sorption behavior of polycyclic aromatic hydrocarbons in soil-water system containing nonionic surfactant. Environ Eng Sci 21:263–272
Zhu H, Yu Y, Ozkan HE, Derksen RC, Krause CR (2008) Evaporation and wetted area of single droplets on waxy and hairy leaf surfaces. Commun Agric Appl Biol Sci 73:711–718
Zoller U (2009) Handbook of detergents. Part F: production, vol 142, Surfactant science series. Taylor and Francis Group, New York
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Castro, M.J.L., Ojeda, C., Cirelli, A.F. (2013). Surfactants in Agriculture. In: Lichtfouse, E., Schwarzbauer, J., Robert, D. (eds) Green Materials for Energy, Products and Depollution. Environmental Chemistry for a Sustainable World, vol 3. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-6836-9_7
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