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Calcium Chloride United States Department of Agriculture Agricultural Marketing Service | National Organic Program Document Cover Sheet https://www.ams.usda.gov/rules-regulations/organic/national-list/petitioned Document Type: ☐ National List Petition or Petition Update A petition is a request to amend the USDA National Organic Program’s National List of Allowed and Prohibited Substances (National List). Any person may submit a petition to have a substance evaluated by the National Organic Standards Board (7 CFR 205.607(a)). Guidelines for submitting a petition are available in the NOP Handbook as NOP 3011, National List Petition Guidelines. Petitions are posted for the public on the NOP website for Petitioned Substances. ☒ Technical Report A technical report is developed in response to a petition to amend the National List. Reports are also developed to assist in the review of substances that are already on the National List. Technical reports are completed by third-party contractors and are available to the public on the NOP website for Petitioned Substances. Contractor names and dates completed are available in the report. Insecticidal Soaps Crops 1 2 Identification of Petitioned Substance 3 4 Chemical Names: 10124-65-9 (Potassium laurate) 5 Potassium Oleate 67701-09-1 (Potassium salts of fatty acids C8-C18 6 Potassium Laurate saturated and C18 unsaturated) 7 Ammonium Nonanoate 8013-05-6 (Castor oil potassium salts) 8 84776-33-0 (Ammonium soaps of fatty acids C8 – 9 Other Names: C18) 10 Potassium Soaps 11 Potassium Salt of Fatty Acids Other Codes: 12 Oleic acid potassium salt EPA Registration No.: 66702-22-70051 (DES-X® 13 Potassium cis-9-octadecenoate Insecticidal Soap Concentrate) 14 Potassium cis-9-octadecenoic acid EPA Registration No.: 1021-1771 (PyGanic® 15 Lauric acid potassium salt Insecticide for Organic Crop Protection) 16 Potassium dodecanoate EPA Registration No.: 10163-324 (M-Pede® 17 Potassium dodecanoic acid Insecticide-Miiticide-Fungicide) 18 Castor oil potassium salts EPA Registration No.: 66702-7-39609 19 Ammonium Soaps (Ammonium soaps of fatty acids) 20 Ammonium Salt of Fatty Acids EPA PC Code: 031801 (Ammonium salts of fatty 21 Perlargonic Acid, Ammonium Salt acids (C8 – C18) 22 EC No.: 205-590-5 (Potassium oleate) 23 Trade Names: EC No.: 233-344-7 (Potassium laurate) 24 Safer® EC No.: 266-933-2 (Potassium salts of fatty acids 25 DES-X® C8-C18 saturated and C18 unsaturated) 26 M-Pede® EC No.: 232-388-4 (Castor oil potassium salts) 27 PyGanic® UNII No.: 74WHF607EU (Potassium oleate) 28 UNII No.: V4361R8N4Z (Potassium laurate) CAS Numbers: UNII No.: 54I68KEO6Y (Castor oil potassium 143-18-0 (Potassium oleate) salts) 29 30 Summary of Petitioned Use 31 32 Soap mixtures have been approved by the United States Department of Agriculture’s (USDA) National Organic 33 Program (NOP) for a range of uses pertaining to crop production. These uses are listed in 7 CFR 205.601 and 34 include applications such as synthetic substances to act as algicides/demossers ((a)(7)), herbicides ((b)(1)), 35 insecticides ((e)(8)), and animal repellants (d). There have been a variety of technical reports that have covered 36 the various applications of soaps within organic agricultural production, including as herbicides (USDA 2011, 37 USDA 2015a, USDA 2015b), animal repellants (USDA 2019a), and insecticides (USDA 1994). 38 39 The purpose of this report is to update the existing technical information available on insecticidal soaps based on 40 more current research (USDA 1994). 41 42 Characterization of Petitioned Substance 43 44 Composition of the Substance: 45 Most insecticidal soaps are composed of potassium salts (or ammonium salts, in some cases) of fatty acids (i.e., 46 fats) (PubChem 23665571, EPA 1992, USDA 1994, NPIC 2001, Jianu 2012, EPA 2013, Certis 2015, Vahabzadeh et 47 al. 2018, Gowan 2019). Insecticidal soaps are composed of a mixture of both saturated fats (all single carbon– ___________________________________ January 2, 2020 Technical Evaluation Report Page 1 of 16 Compiled by Savan Group for the USDA National Organic Program Technical Evaluation Report Insecticidal Soaps Crops 48 carbon bonds) and unsaturated fats (containing multiple carbon–carbon bonds) and contain a variety of carbon 49 chains (Anneken et al. 2012, AMVAC 2015, Thomas et al. 2016, USDA 2019a). 50 51 Most commercially relevant fatty acids consist of linear carbon chains with a length of six to twenty-two carbons, 52 with soaps frequently containing eight to eighteen carbon chains. Ammonium nonanoate (9 carbons) is among 53 the most prevalent short-chained soaps while potassium oleate and potassium laurate (18 carbons) are among the 54 most prevalent long-chained soaps (EPA 2000, USDA 2011, Anneken et al. 2012, EPA 2013, USDA 2015a, USDA 55 2015b, USDA 2019a). 56 57 Source or Origin of the Substance: 58 Insecticidal soaps are manufactured by subjecting natural fatty acids (from both animal and plant sources) 59 to the process of saponification (Equation 1 in Evaluation Question 2). The saponification process 60 hydrolyzes the linkages in the natural fatty acid (derived from animal fats or plant oils) in the presence of a 61 base, specifically potassium hydroxide (KOH) (Nora and Koenen 2010, USDA 2011, Anneken et al. 2012, 62 Jianu 2012). The cation (positively charged ion) for soap molecules is determined by the base used in its 63 production. Potassium soaps are derived from the treatment of fatty acids with potassium hydroxide 64 (KOH), while ammonium soaps are produced by saponification with ammonium hydroxide (NH4OH) or 65 ammonia (NH3, which forms NH4OH when dissolved in water) (Anneken et al. 2012, AMVAC 2015, USDA 66 2015a, USDA 2015b). 67 68 Properties of the Substance: 69 The chemical and physical properties of insecticidal soaps are dependent on the length of the carbon chain. 70 Longer carbon chains produce a more nonpolar molecule, which increases the hydrophobicity of the soap 71 product (Anneken et al. 2012, EPA 2013, USDA 2015a, USDA 2015b, USDA 2019a). As a result, long chain 72 insecticidal soaps have reduced water solubility compared to soaps with shorter carbon chains, which bear 73 a larger ratio of negative charge per molecular weight. 74 75 Since commercial soaps consist of a range of possible chain lengths (8–18), their water solubility varies 76 (although they trend toward low water solubility) (Anneken et al. 2012, USDA 2015a, USDA 2015b, USDA 77 2019a). The properties of mixed-chain potassium and ammonium soaps, including short and long chain 78 lengths with ammonium nonanoate (short, C9) and potassium oleate and potassium laurate (long, C18), are 79 summarized below in Table 1 (EPA 2000, EPA 2013, USDA 2015a, USDA 2015b, USDA 2019a). 80 81 Table 1. Properties of Insecticidal Soaps 82 Compound Potassium Potassium Potassium Potassium salts Ammonium Ammonium Oleate Laurate Soaps C8 – of Castor Oil Soaps C8 – C18 Nonanoate C18 CAS No. 143-18-0 10124-65-9 67701-09-1 8013-05-6 84776-33-0 63718-65-0 Molecular 320.6 g/mol 238.41 1101.7 g/mol N/A 175.27 g/mol Weight g/mol General Brown or Liquid Yellow to N/A Brown to Clear/pale Appearance yellow solid, amber white/clear liquid, clear to amber liquid, liquid, slight solution when musty or ammonia ammonia odor mixed with soap odor and/or soapy water, faint odor soapy odor Solubility 25 g/ 100 mL N/A Dispersible N/A Water Insoluble Water Soluble water in water Melting Point 235-240 oC N/A N/A N/A -1 oC N/A Boiling Point N/A N/A N/A N/A 101 oC 104.4 oC Specific 1.1 N/A 1.02 – 1.04 N/A 0.80 – 0.988 1.0 Gravity pH N/A N/A 8.60 - 10.2 7 – 10 8 – 9 83 Sources: AMVAC 2015, Certis 2015, Schultz Company 2016, BioSafe Systems 2017, Gowan 2019, PubChem 84 23675775, PubChem 72941488, PubChem 176286868, PubChem 23665571, PubChem 21902950 January 2, 2020 Page 2 of 16 Technical Evaluation Report Insecticidal Soaps Crops 85 86 Specific Uses of the Substance: 87 Soaps have a variety of uses for organic agricultural crop production, including as an herbicide for the 88 control of mosses, algae, and weeds (USDA 2015a, USDA 2015b). In addition, soaps are also used as animal 89 repellants and as insecticides (USDA 1994, USDA 2019a). Within organic agriculture, the application of 90 insecticidal soaps includes their use as “acaricides or mite control,” as stipulated in 7 CFR 205.601. 91 92 Insecticidal soaps are used for the treatment of many crops and ornamental species for the control of 93 aphids, whiteflies, mealy bugs, webworms, lace bugs, leafhoppers, thrips, and other sucking insects and 94 pests (NPIC 2001, Southside 2009, Sarwar and Salman 2015, Qureshi and Stansly 2016, Razze et al. 2016, 95 Alston et al. 2018). Insecticidal soaps are generally broad-spectrum insecticides that have shown little 96 toxicity to non-target species and are known to be effective across a range of crops (Rebek and Hillock 97 2016, NPIC 2001, Southside 2009, Razze et al. 2016, Alston et al. 2018, Vahabzadeh et al. 2018). 98 99 Approved Legal Uses of the Substance: 100 The United States Food and Drug Administration (FDA) has approved the use of “salts of volatile fatty 101 acids,” specifically “ammonium salts of mixed 5-carbon acids,” and the “ammonium salt of isobutyric 102 acid” for use “as a source of energy in dairy cattle feed” at 21 CFR 573.914. The FDA has also approved the 103 use of “salts of fatty acids” for use “in food and in the manufacture of food components” at 21 CFR 172.863. 104 However, this usage has not been extended to fatty acid salts with ammonium cations. 105 106 The United States Environmental Protection Agency (EPA) has described the manufacture of soap at 40 107 CFR 417.30 as the “neutralizing refined fatty acids with an alkaline material in approximately 108 stoichiometric amounts.” The EPA has designated “soap” as an inert ingredient permitted in minimum risk 109 pesticide products, which has been granted “exemptions for pesticides of a character not requiring [Federal 110 Insecticide, Fungicide, and Rodenticide Act] FIFRA regulation” at 40 CFR 152.25.
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