              OFFICE OF CHEMICAL SAFETY
AND POLLUTION PREVENTION
                 UNITED STATES ENVIRONMENTAL PROTECTION AGENCY
                            WASHINGTON, D.C.  20460







MEMORANDUM

DATE:		January 3, 2013

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 Codes: 069037 and 069038
            CAS Number: 3391-86-4 and 3687-48-7
            Type of Review: Product Chemistry Assessment

FROM:		Colin G. Walsh, M.S., Biologist  /s/  01/03/2013	
            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 biopesticides, 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.  










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 (R-Octenol).

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 typically 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 adequately 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-ol
Molecular Weight
128.21
PC Code
069037
CAS Registry Number
3391-86-4
Empirical Formula
C8H16O
Registration Review Case Number
6033
Chemical Structure
                                       


Table 2. Product 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
C8H16O
Registration Review Case Number
6033
Chemical Structure
                                       



Product Chemistry Summary 
The Agency has conducted reviews 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, 2007a). 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 Composition
                                       A
Refer to Tables 1 and 2.
                                       -
830.1200
Description of starting materials, production and formulation process
                                       A
CBI
                                       -
830.1400
Discussion of formation of impurities
                                       A
CBI
                                       -
830.1700
Preliminary analysis
                                       A
CBI
                                       -
830.6302
Color
                                       A
Colorless to pale yellow
                                   45415201
830.6303
Physical state
                                       A
Liquid at room temperature
                                   45415201
830.6304
Odor
                                       A
Earthy
                                   45415201
830.6313
Stability to normal and elevated temperatures, metals and metal ions
                                       A
Stable at 54°C for 14 days; chemical not expected to be in contact with metals. 
                              45503901; 45585601
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] mol/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 Protection 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.pdf

Maloney, R. 2001. Product Chemistry of Bedoukian Octenol Technical. Unpublished study prepared by 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/. 01/03/2013.



cc: Colin G. Walsh, Leonard Cole, BPPD Science Review File, IHAD/ARS, Colin G. Walsh, FT, PY-S, January 3, 2013

