1,4 - DMN; 2,6 - DIPN

055802; 055803 UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

**MEMORANDUM DATE:**  August 22 , 2012 **SUBJECT** : Product Chemistry Scoping Document for the Registration Review of Dimethylnaphthalene (1,4 **Registration Review Case #: PC Code**  **s :**  **055802, 055803 CAS Numbers:**  **571 -**  **Chemical Class: Biochemical**  **Review Type: Product Chemistry FROM:**  Gina Burnett , M.S., Biologist

Biochemical Pesticides Branch Biopesticides & Pollution Prevention Division (7511P) **TO :**  Colin Walsh , Regulatory

Biochemical Pesticides Branch Biopesticides & Pollution Prevention Division (7511P) **AND :**  Leonard Cole , Regulatory

Biochemical Pesticides Branch Biopesticides & Pollution Prevention Division (7511P) **ACTION REQUESTED** A preliminary

assessment of available information on product chemistry data associated with the biopesticide s 1,4 - dimethylnaphthalene (1,4 in support of the development of a Registration Revie Registration Review

UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON, D.C. 20460

OFFICE OF CHEMICAL SAFETY AND POLLUTION PREVENTION

Product Chemistry

Scoping Document for the Registration Review of Dimethylnaphthalene (1,4 - DMN) and 2,6 - Diisopropylnaphthalene (2,6 **Registration Review Case #: 6029** 

**055802, 055803**

**- 58**  **- 4, 24157**  **- 81**  **- 1**  **Biochemical Review Type: Product Chemistry** 

M.S., Biologist /s/ 8/22/12 Biochemical Pesticides Branch Biopesticides & Pollution Prevention Division (7511P)

, Regulatory Action Leader Biochemical Pesticides Branch Biopesticides & Pollution Prevention Division (7511P)

, Regulatory Action Leader Biochemical Pesticides Branch Biopesticides & Pollution Prevention Division (7511P)

A preliminary

assessment of available information on product chemistry data associated with the imethylnaphthalene (1,4 - DMN) and 2,6 - diisopropylnaphthalene (2,6 in support of the development of a Registration Revie w Work Plan. Registration Review Case #: 6029 Product Chemistry

OFFICE OF CHEMICAL SAFETY AND POLLUTION PREVENTION

Product Chemistry

Scoping Document for the Registration Review of 1,4 -

Diisopropylnaphthalene (2,6 - DIPN) .

A preliminary

assessment of available information on product chemistry data associated with the iisopropylnaphthalene (2,6 - DIPN)1,4 - DMN; 2,6 - DIPN Registration Review Case #: 6029

055802; 055803 Product Chemistry **Introduction** The A genc y has determined that all necessary product chemistry information is available on the pesticide active ingredients 1,4 - dimethylenaphthalene (1,4 - DMN) and 2,6 - diisopropylnaphthalene (2,6 - DIPN) with the exception of the UV/Visible light absorption data requirement (OCSPP Guideline 830.7050). This data requirement has not been fulfilled for either chemical . The Agency requires UV/Visible light absorption data for all technical grade active ingredients. 1,4 - DMN is a biochemical pesticide intended for use as a growth regulator (potato sprout inhibitor) . The first product containing this active ingredient was registered with the Agency in 1994. Currently , there are four active registrations containing 1,4 - DMN; one manufacturing use product (MUP) and three end - use products (EPs). A tolerance exemption listed at 40 CFR 1180.1142 establishes an exemption from the requirement of a tolerance for residues of 1,4 - DMN wh en applied post harvest to potatoes in accordance with good agricultural practices . 2,6 - DIPN is also a biochemical pesticide intended for use as a growth regulator (potato sprout inhibitor) . The first product containing this active ingredient was registered with the Agency in 2003. Currently , there are two active regi strations containing 2,6 - DIPN . A tolerance for residues listed at 40 CFR 180.590 establishes residue levels for 2,6 - DIPN and its metabolites and degredates in potato, cattle, goat horse, milk and sheep. Concerning the product chemistry of 1,4 - DMN and 2,6 - DIPN, all biochemical pesticide data requirements for the technical grade active ingredient s have been satisfied and are summarized in Table s 3 and 4 , resp ectively . UV/Visible light absorption data is the only product chemistry data outstanding for the products currentl y registered. F uture registrations must adequatel y address all of the biochemical pesticides product chemistry data requirements.1,4 - DMN; 2,6 - DIPN Registration Review Case #: 6029

055802; 055803 Product Chemistry

3 **Table 1. Product Identity and Composition for 1,4**  **- DMN**  **Common Name** 1,4 - D imethylnaphthalene ( 1,4 - DMN ) **Chemical Name, IUPAC** Naphthalene, 1,4 - dimethyl **Molecular Weight** 156.22 **PC Code** 055802 **CAS Registry Number** 571 - 58 - 4 **Empirical Formula** C12H12 **Registration Review Case Number** 6029 **Chemical Structure**

**Table 2 . Product Identity and Composition for 2,6**  **- DIPN**  **Common Name** 2,6 - Diisopropylnaphthalene (2,6 - DIPN ) **Chemical Name, IUPAC** Nap hthalene, 2,6 - bis(1 - methylethyl) **Molecular Weight** 212.33 **PC Code** 055803 **CAS Registry Number** 24157 - 81 - 1 **Empirical Formula** C16H20 **Registration Review Case Number** 6029 **Chemical Structure**1,4 - DMN; 2,6 - DIPN Registration Review Case #: 6029

055802; 055803 Product Chemistry

4 **Product Chemistry Summary** The Agency

has conducted a review of the available product chemistry data and information for 1,4 - DMN . These data are summarized in Table 3, below. **Table 3 . Biochemical Pesticides Product Che**  **mi stry Data Requirements for 1,4**  **- DMN**  **Guideline No. Physical and Chemical** 

**Properties Status**  **1 Value**  **MRID 830.1100**  Product Identity and

Com position A Refer to Table 1. - **830.1200** Description of starting

materials, production and formulation process A CBI - **830.1400** Discussion of formation of

im purities A CBI - **830.1700** Preliminary analysis A CBI - **830.6302** Color A Pale yellow to colorless 43082506 **830.6303** Phy sical state A Liquid at room tem perature 43082506 **830.6304** Odor A Petroleum distillate 43082506 **830.6313** Stability to normal and

elevated temperatures, metals and metal ions A Stable at normal tem p.; 6 - 7% loss at elevated tem p.; stable in presence of metals. 43082509

**830.7000** pH A 5.9 at 25 o C 43082506 **830.7050** UV/Visible light absorption N/D - - **830.7200** Melting point/melting range N/A N/A; not a solid - **830.7220** Boiling point/boiling range A 264 o C 43280506 **830.7300** Density A 1.014 g/ml at 25 o C 43280506 **830.7520** Particle size, fiber length,

and diameter distribution N/A N/A; soluble in water - **830.7550 830.7560**  **830.7570** Partition coefficient (n Octanol/Water) N/A N/A; soluble in water - **830.7840** Water solubility A Soluble at 5.1ppm 43082507 **830.7950** Vapor pressure A 1.88x10 - 2 Torr at 25 o C 43082508 1. A= Acceptable. N/A=Not Applicable. N/D=Not Determined.1,4 - DMN; 2,6 - DIPN Registration Review Case #: 6029

055802; 055803 Product Chemistry

5 The Agency

has conducted a review of the available product chemistry data and information for 2,6 - DIPN . These data are summarized in Table 4 , below. **Table 4**  **. Biochemical Pesticides Product Chemistry Data Requirements for 2,6**  **- DIPN**  **Guideline No. Physical and Chemical** 

**Properties Status**  **1 Value**  **MRID 830.1100**  Product Identity and

Com position A Refer to Table 1. - **830.1200** Description of starting

materials, production and formulation process A CBI - **830.1400** Discussion of formation of

im purities A CBI - **830.1700** Preliminary analysis A CBI - **830.6302** Color A Munsell color systems: N 9.5 90.0% R 44614103 **830.6303** Phy sical state A Crystalline solid at 25 o C 44614103 **830.6304** Odor A No noticeable odor 44614103 **830.6313** Stability to normal and

elevated temperatures, metals and metal ions A Stable at normal and elevated tem peratures; stable in presence of Al and Zn, 7% reduction in presence of Cu 44614103

**830.7000** pH A 6.00 at 20 o C 44614103 **830.7050** UV/Visible light absorption N/D - - **830.7200** Melting point/melting range A 67.8 o C to 68.9 o C 44614103 **830.7220** Boiling point/boiling range N/A N/A; not a liquid - **830.7300** Density A 0.49 g/ml at 25 o C 44614103 **830.7520** Particle size, fiber length,

and diameter distribution N/A N/A; soluble in water - **830.7550 830.7560**  **830.7570** Partition coefficient (n Octanol/Water) A Soluble in 1 - octanol at 39,559ppm 44614103 **830.7840** Water solubility A 0.02ppm 44614103 **830.7950** Vapor pressure A 6.1x10 - 4 Torr at 2 5 o C 44614103 1. A= Acceptable. N/A=Not Applicable. N/D=Not Determined.1,4 - DMN; 2,6 - DIPN Registration Review Case #: 6029

055802; 055803 Product Chemistry

6 **References** Irving, J.W., Pesticide Assessment Guidelines, Subdivision M, Series: 151 - 17, (Phy sical and Chemical Properties). Study performed by

DARTEC, Inc. and submitted to EPA by Plate Chemical Co. MRID 446141 - 03. 1998 . Lorence, P.J., Vargyas, L.D., and J.R. Marat. 1,4 - DMN Batch H5510 - Color, Phy sical State, Odor, Boiling Point, Specific Gravity , PH, Flammability , Impact Explodability, Viscosity , Lab Project Number 4373 - 93 - 0226 - AS. Private study performed by

Ricerca, In c. and submitted to EPA by D - I - 1 - 4, Inc. MRID 430 825 - 06 . 1993. Lorence, P.J., Vargyas, L.D., and J.R. Marat. 1,4 - DMN Solubility, Lab Project Number 4373 - 93 - 0250 - AS . Private study

performed b y Ricerca, Inc. and submitted to EPA by D - I - 1 - 4, Inc. MRID 430825 - 07. 1993. Lorence, P.J., Vargyas, L.D., and J .R. Marat. 1,4 - DMN

– Vapor Pressure. Lab Project Number 4373 - 93 - 0249 - AS. Private study performed by

Ricerca, Inc. and submitted to EPA by D I - 1 - 4, Inc. MRID 430825 - 08 . 1993. Lorence, P.J., Vargyas, L.D., and J.R. Marat. 1,4 - DMN Stability, Lab Project Number 4373 - 93 - 0247 - AS. Private study

performed b y Ricerca, Inc. and submitted to EPA by D - I - 1 - 4, Inc. MRID 430825 - 09 . 1993. National Organic Standards Board Technical Advisory Panel (TAP) Review . 1,4 - dimethylnaphthalene for use as a post - harvest adjuvant . http://www.ams.usda.gov/AMSv1.0/getfile?dDocName=STELPRDC5057592 . 8/14/2012. PubChem. http://pubchem.ncbi.nlm.nih.gov/ . 8/14/2012 .