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Fosetyl-Aluminium (302) Phosphonic Acid (301)

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Fosetyl-Aluminium (302) Phosphonic Acid (301) 1405 FOSETYL-ALUMINIUM (302) PHOSPHONIC ACID (301) The first draft was prepared by Mr D Lunn, Ministry for Primary Industries, Wellington, New Zealand EXPLANATION Fosetyl (and its aluminium salt) and phosphonic acid (formulated as the potassium or sodium salts) are systemic fungicides with protectant action against a number of oomycete and ascomycete fungi and some plant pathogenic bacteria in a range of fruit, vegetables and ornamental crops. They are rapidly absorbed through both leaves and roots and exhibit both acropetal and basipetal translocation. Their mode of action is by inhibiting germination of spores and by blocking development of mycelium, competing with phosphate as allosteric regulator of several enzymes. In addition, they can induce direct or indirect production of phytoalexin and pathogenesis-related proteins leading to an induction of plant defence mechanisms against fungal or bacterial pathogens. Authorisations exist in many countries for the use of fosetyl or its aluminium salt (fosetyl-Al) as a pre-plant dip, foliar, drench or drip-irrigation treatments and authorisations also exist for phosphonic acid (formulated as the monopotassium, dipotassium or sodium salts) in a number of countries for use as a trunk injection, pre-plant dip, foliar, soil and post-harvest treatments. Fosetyl and phosphonic acid were scheduled by the 48th Session of the CCPR as a new compounds for consideration by the 2017 JMPR. Residue and analytical aspects were considered for the first time by the present meeting. The Meeting was provided with studies on metabolism, analytical methods, supervised field trials, processing, freezer storage stability and environmental fate in soil. IDENTITIES For fosetyl-aluminium, pesticide specifications have been established by the Joint FAO/WHO Meeting on Pesticide Specifications (JMPS) and published as FAO Specifications and Evaluations for Agricultural Pesticides (2013). (http://www.fao.org/agriculture/crops/thematic-sitemap/theme/pests/jmps/en/). 1406 Fosetyl-Aluminium Fosetyl Fosetyl-aluminium ISO common fosetyl (refers to the acid) fosetyl-aluminium names: (derived name for the aluminium salt) IUPAC name: ethyl hydrogen phosphonate aluminium tris-ethylphosphonate Chemical Abstracts ethyl hydrogen phosphonate aluminium tris-O-ethylphosphonate names: Synonyms efosite efosite-Al phosphonic adid ethyl ester CAS number 15845-66-6 39148-24-8 Molecular mass: 110.0 354.1 Molecular formula C2 H7 O3 P C6 H18 Al O9 P3 Structural formula: Phosphonic acid (phosphorous acid) is the active constituent in authorised products containing either a mixture of mono- and di-potassium phosphonate ions (referred to as ‘potassium phosphonates’), or the ammonium or dibasic sodium phosphonates. The Meeting was provided with information only on the potassium phosphonates compound. Phosphonic acid Potassium phosphonates Common names: phosphonic acid potassium hydrogen dipotassium phosphonate phosphonate IUPAC name: phosphonic acid reaction mixture of potassium hydrogen phosphonate and dipotassium phosphonate Chemical Abstracts phosphonic acid reaction mixture of potassium hydrogen phosphonate and name: dipotassium phosphonate Synonyms phosphorous acid monopotassium phosphite potassium dihydrogen phosphite CAS number 13598-36-2 13977-65-6 13492-26-7 Molecular mass: 82 120.1 158.2 Molecular formula H3PO3 KH2PO3 K2HPO3 Structural formula: Formulations of fosetyl and fosetyl-aluminium are available in a number of formulations, often mixed with one or more other fungicides. Fosetyl-Aluminium 1407 Active ingredient Formulation types Other active ingredients fosetyl SL (Soluble concentrate) propamocarb fosetyl-aluminium WG (Water dispersible granule) - copper cymoxanil, folpet fenamidone fluopicolide folpet, iprovalicarb folpet iprovalicarb, mancozeb metiram-zinc WP (Wettable powder) - captan copper cymoxanil, folpet fenamidone, iprovalicarb mancozeb trifloxystrobin WS (water dispersible powder for thiabendazole, thiram slurry seed) Phosphonic acid is available as ammonium, sodium or potassium salts, and for consistency, the active ingredient content is usually expressed as the acid equivalent. Formulations of potassium phosphonates manufactured from technical concentrates containing about 32% phosphonate ions and up to 20.0% potassium include: Active ingredient Formulation types Phosphonic acid SL (Soluble concentrate) As potassium, sodium and/or amonium (phosphorous acid) salts of phosphonic acid PHYSICAL AND CHEMICAL PROPERTIES Fosetyl-aluminium Table 1 Physical and chemical data of fosetyl-aluminium (active ingredient and technical grade material) Test or Study & Test material purity and Findings and comments Reference Annex point specification Melting point Pure ai (99.1%) 215 °C R009286 Technical (97.6%) 207-210 °C M-179033-01-1 Boiling point Pure ai (99.1%) Not measured- decomposition at >190 °C R009286 Technical (97.6%) Not measured- decomposition at >190 °C M-179033-01-1 Relative density Pure ai (99.1%) 1.529 (20 °C) R009286 Technical (97.6%) 1.54 (20 °C) M-179033-01-1 Vapour pressure Pure ai (98%) < 10–7 Pa at 25 °C (extrapolated) R009300 M-179047-01-1 pH Technical (97.6%) 3.1 in 1% aqueous suspension R009295 M-179042-01-1 Henry’s law constant calculated KH < 3.2 Pa m³/mol (20 °C) R009300 M-179047-01-1 Appearance Pure ai (99.1%) white powder R009286 Technical (97.6%) white powder M-179033-01-1 Solubility in water Pure ai (99.1%) 111.3 g/L in pure water at pH 6 R009291 (20 °C) 111.4 g/L in buffer at pH 5.1 M-179038-01-1 109.8 g/Lin buffer at pH 8.6 1408 Fosetyl-Aluminium Test or Study & Test material purity and Findings and comments Reference Annex point specification Solubility in organic Technical (97.6%) Solvent Solubility (mg/L) R009291 solvents Dichloromethane 4 M-179038-01-1 (mg/L, 20 °C) Acetone 6 Acetonitrile: 1 Ethyl acetate: < 1 Methanol: 807 o-Xylene: 1 n-Octanol: 10 n-Heptane: < 1 Octanol/water Pure ai (99.1%) Log POW -2.11 at 21-23 °C R011712 partition coefficient M-184417-01-1 Hydrolysis Pure ai (99.1%) Stable (< 10% degradation) for 1 month at pH 5-9, 22 °C R000987 (sterile water in the DT50 5 days at pH 3 and 22 °C M-159693-01-1 dark) Technical (97.6%) Stable for 5 days at pH4-9, 50 °C C012596 M-159693-01-1 The JMPS evaluation of fosetyl-aluminium noted that when fosetyl-aluminium dissolves in sterile water it dissociates and the liberated aluminium (Al3+) ions tend to form aluminium hydroxide (which may precipitate or flocculate in the spray tank), while the liberated acidic fosetyl ions tend to be hydrolysed (more rapidly in biological systems), with the formation of phosphonic/phosphorous acid and ethanol. This complex behaviour in water has important implications for the product specifications and the data relating to water solubility, octanol/water partition coefficient and hydrolysis. Potassium phosphonates Table 2 Physical and chemical data of potassium phosphonates (technical grade material) Test or Study & Annex Test material purity and Findings and comments Reference point specification Melting point Technical concentrate 73 °C (acid) PPDB Boiling point Technical concentrate Decomposes before boiling PPDB Relative density Technical concentrate 1.651 (20 °C) PManual pH Technical concentrate 5.9-6.4 EFSA Appearance Technical concentrate Hygroscopic, delequescent white crystals PManual Solubility in water Technical concentrate 425 g/litre PManual (20 °C) 500 g/litre PPDB Dissociation constant Phosphonic acid pK1 = 2.0 , pK2 = 6.59 EFSA UV absorption Technical concentrate λmax = 198 nm - absorbance = 1.7859 EFSA No absorption after 200 nm Octanol/water partition Technical concentrate Not applicable (insoluble in n-octanol) PMRA coefficient EFSA: Conclusion on the peer review of the pesticide risk assessment of the active substance potassium phosphonates. EFSA Journal 2012;10(12):2963 PPDB: Pesticide Properties Database (http://sitem.herts.ac.uk/aeru/ppdb/en/index.htm) PManual: The Pesticide Manual, 15th Edition. BCPC METABOLISM AND ENVIRONMENTAL FATE The Meeting received metabolism studies for fosetyl-Al on plants (citrus, apples, grapes, pineapple and tomato) and animals (rats, lactating goats) and also received environmental fate and rotational crop studies for fosetyl-Al and phosphonic acid. In this evaluation, information relating to "phosphonic (phosphorous) acid" formed as a major metabolite is reported as the free acid. After application, aluminium tris-O-ethyl phosphonate (i.e. fosetyl-Al) dissociates into the O-ethyl phosphonate and aluminium ions. Any phosphonate formed Fosetyl-Aluminium 1409 from O-ethyl phosphonate in biological systems would never be present in the form of the free acid (i.e. phosphonic acid) under physiological and environmental conditions (pH 4 to 9). This conclusion is supported by the molecular structure and by the dissociation constant observed (dissociation constant for the first step of deprotonation: pKa = 2.0). Consequently, phosphonates in their fully protonated form are strong acids that spontaneously form salts in contact with soil or natural water with any suitable counter ion present (i.e. sodium, potassium, magnesium, calcium). With the ability to readily form salts in the environment, in terms of their acidic or alkaline character, phosphonates are similar to the salts of phosphoric acid (i.e. phosphates) in their environmental behaviour. In solution, phosphonic acid is in equilibrium with phosphorous acid, such that essentially all of the molecules are present as phosphonic acid The studies investigating the environmental fate of fosetyl-aluminium
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