3 - decen- 2 - one DP Number: 373085

PC Code: 068403 EPA File Symbol No.: 5481 - LAI Ty pe of Review: Human Health Toxicity

OFFICE OF CHEMICAL SAFETY AND POLLUTION PREVENTION **UNITED ST AT**  **ES ENVIRONMENT AL**  **PROTECTION A GENCY** 

WASHINGTON, D.C. 20460

**MEMORANDUM DATE:**  January 3 , 201 3 **SUBJECT** : Preliminary Product Chemistry Assessment for the Registration Review of 1 -

Octen - 3 - ol (Octenol) and (R) - ( - ) - 1 - Octen - 3 - ol (R- Octenol) . **Registration Review Case Number:** 6033 **Chemical Class:** Biochemical **PC Code s**  **:** 069037 and 069038 **CAS Number:** 3391 - 86 - 4 and 3687 - 48 - 7 **Type of Review:** Product Chemistry Assessment **FROM:** Colin G. Walsh, M.S. , Biologi st /s/ 0 1 /03 /201 3

Biochemical Pesticides Branch Biopesticides & Pollution Prevention Division (7511P) **TO :**  Leonard Cole , Senior Regulatory Action Leader Biochemical Pesticides Branch Biopesticides & Pollution Prevention Division (7511P ) **ACTION REQUESTED** The following scoping document contains the preliminary product chemistry assessment for the biopesticide s , 1 - Octen - 3 - ol (Octenol) and (R) - ( - ) - 1 - Octen - 3 - ol (R- Octenol) , in support of the development of the Registration Review Preliminary Work Plan.Octenol and R- Octenol P C Code s : 069037 and 069038

Ty pe of Review: Product Chemistry Assessment (Registration Review)

2 **Introduction** The Agency has determined that all necessary product chemistry information is available on the pesticide active ingredients , 1 - Octen - 3 - ol (Octenol) and (R) - ( - ) - 1 - Octen - 3 - ol (ROctenol) . Octenol is a biochemical pesticide intended for use as an attractant for certain species of mosquitoes, biting flies, and other biting insects; however, the chemical itself does not kill insects. Octenol is ty

pically used in conjunction with carbon dioxide and electronic devices that in turn kill the trapped insects. This form of Octenol, 1 - Octen - 3 - ol, is the racemic mixture and includes all isomers of this chemical. The first product containing this active ingredient was registered with the Agency in 1996 . Currently, there are seven active registrations containing Octenol ; one manufacturing -use product (MP) and six end-use products (EPs). R- Octenol is also a biochemical pesticide intended for use as an attractant for certain species of mosquitoes and other biting insects; however, the chemical itself does not kill insects. As with Octenol, R- Octenol is typically used in conjunction with carbon dioxide and electronic devices that in turn kill the trapped insects. This form of Octenol, (R) - ( - ) - 1 - Octen - 3 - ol , is a single isomer from the racemic mix. The first product containing this active ingredient was registered with the Agency in 2007 . Currently, there are two active registrations containing R- Octenol ; one MP and one EP . Concerning the product chemistry of Octenol and R- Octenol, all biochemical pesticide data requirements for the technical grade active ingredients have been satisfied and are summarized in Table 3. UV/Visible light absorption data is the only product chemistry

data outstanding for the products currently

registered. Future registrations must adequatel y address all of the biochemical pesticides product chemistry data requirements.

**Table 1. Product Identity and Composition for**  **1 -**  **Octen -** **3 -**  **ol Common Name**  1 - Octen - 3 - ol (Octenol) **Chemical Name, IUPAC** oct - 1 - en - 3 - olOctenol and R- Octenol P C Code s : 069037 and 069038

Ty pe of Review: Product Chemistry Assessment (Registration Review)

3 **Molecular Weight** 128.21 **PC Code** 0 69037 **CAS Registry Number** 3391 - 86 - 4 **Empirical Formula** C 8 H 16 O **Registration Review Case Number** 6033 **Chemical Structure**

**Table 2. Produ ct Identity and Composition for (R)**  **- (**  **- )**  **- 1**  **- Octen**  **- 3**  **- ol**  **Common Name** (R) - ( - ) - 1 - Octen - 3 - ol (R- Octenol) **Chemical Name, IUPAC** oct - 1 - en - 3 - ol **Molecular Weight** 128.22 **PC Code** 069038 **CAS Registry Number** 3687 - 48 - 7 **Empirical Formula** C 8 H 16 O **Registration Review Case Number** 6033Octenol and R- Octenol P C Code s : 069037 and 069038

Ty pe of Review: Product Chemistry Assessment (Registration Review)

4 **Chemical Structure**

**Product Chemistry Summary** The Agency

has conducted review s of the available product chemistry data and information for Octenol and R- Octenol . During the registration of the active ingredient, R- Octenol, the registrant requested to bridge the physical and chemical characteristics from Octenol to R- Octenol. The bridging request was acceptable to the Agency (EPA, 2007 a) . These data are summarized in Table 3, below. **Table 3. Biochemical Pesticides Product Chemistry Data Requirements for**  **Octenol and R** **** **Octenol Guideline No.**  **Physical and Chemical**

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

Com position A Refer to Table s 1 and 2 . - **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 Colorless to p ale yellow 45415201 **830.6303** Physical state A Liquid at room tem perature 45415201 **830.6304** Odor A Earthy 45415201 **830.6313** Stability to normal and

elevated temperatures, A Stable at 54°C for 14 days; 45503901;

45585601Octenol and R- Octenol P C Code s : 069037 and 069038

Ty pe of Review: Product Chemistry Assessment (Registration Review)

5 metals and metal ions chemical not expected to be in contact with metals . **830.7000** pH N/A N/A; not soluble or dispersible in water - **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 175 o C at 760 mm Hg 45415201 **830.7300** Density A 0.84 g/ml at 25 o C 45415201 **830.7520** Particle size, fiber length,

and diameter distribution N/A N/A; not a solid - **830.7550 830.7560**  **830.7570** Partition coefficient (n Octanol/Water) A Kow = 105 (estimated) 45415201 **830.7840** Water solubility A 9.7 x 10 - 8 mo l/L (estimated) 45415201 **830.7950** Vapor pressure A 0.5 mm Hg at 20°C (estimated) 45415201 1. A= Acceptable. N/A=Not Applicable. N/D=Not Determined. **References** EPA. 2002. Memorandum from Paul Zubkoff to Todd Peterson. Chemistry Reviews of Bedoukian (2E) - 1 - octen - 3 - ol Technical . U.S. Environmental Protection Agency Office of Pesticide Programs. January 17, 2002. EPA. 2006. Memorandum from Russell S. Jones to Todd Peterson. Science Review in Support of the Registration of the Manufacturing Use Product , Roctenol, Containing 98% (R) - ( - ) - 1 - Octen 3 - ol, A New Active Ingredient. Review of Product Chemistry, Tier 1 Toxicity Studies and Waiver Requests, Tier 1 Non - Target Organism Waiver Requests, and Endangered Species Risk Assessment. U.S. Environmental Prote ction Agency Office of Pesticide Programs. November 7, 2006. EPA. 2007a. Memorandum from Nina Simeonova to Todd Peterson. Response to the deficiency letter submitted in support of application for registration of Roctenol TGAI, containing 98% (R) - ( - ) - 1 - octen - 3 - ol as its active ingredient. U.S. Environmental Protection Agency Office of Pesticide Programs. June 18, 2007. EPA. 2007b. Biopesticides Fact Sheet for 1 - Octen - 3 - ol (069037) & R- ( - ) - 1 - Octen - 3 - ol (069038). U.S. Environmental Protection Agency Office of Pesticide Programs. July 5, 2007. http://www.epa.gov/opp00001/chem_search/reg_actions/registration/fs_G - 126_05 - Jul - 07.pdfOctenol and R- Octenol P C Code s : 069037 and 069038

Ty pe of Review: Product Chemistry Assessment (Registration Review)

6 Maloney, R. 2001 . Product Chemistry of Bedoukian Octenol Technical. Unpublished study prepared b y Bedoukian Research, Inc. 34 p. MRID 45415201. Maloney, R. 2001 . Supplemental Product Chemistry for Bedoukian Octenol Technical. Unpublished study

prepared by

Bedoukian Research, Inc. 6 p. MRID 45503901. Maloney, R. 2002. Supplemental Product Chemistry for Bedoukian Octenol Technical. Unpublished study

prepared by

Bedoukian Research Inc. 10 p. MRID 45585601 Pesticide Chemical Search. http://iaspub.epa.gov/apex/pesticides/f?p=CHEMICALSEARCH:1 : . 01/03 /2013. PubChem. http://pubchem.ncbi.nlm.nih.gov/ . 01/0 3 /201 3 . cc: Colin G. Walsh, Leonard Cole , BPPD Science Review File, IHAD/ARS, Colin G. Walsh, FT, PY - S, January 3 , 201 3