Spongy Moth Lures

Attachment 2 Statement of Work Spongy Moth lure (Lymantria dispar), (+) disparlure Background and General Information Pheromones are sensitive detectors of specific moths and non-indigenous forest insect pests which allow for monitoring insect populations and aid a variety of control strategies. Lymantria dispar (spongy moth) are one of the most serious exotic plant pests threatening United States (U.S.) agriculture. Living with spongy moth infestations, if not detected, monitored, and managed, would be damaging to U.S. agriculture and the forest industry. Further, the cost of eradication could be in the millions of dollars. The spongy moth pheromone is used to detect previously unknown infestations of spongy moth. Pheromone lure usage rates will vary from year to year, but the importance of this program is well established. Specifications (+) disparlure = (cis-7,8-Epoxy-2-methyloctadecane) Disparlure required purity: 1. Colorless clear liquid (slight straw discoloration may be tolerated) 2. Completely distillable at 110 degrees C < 0.5 mm (0.5% residue) 3. Refractive index n 1.4435 +/- 0.001 4. IR and NMR (match standard) 5. Contains > 95% cis-7,8-epoxy-2-methyloctadecane as measured by gas chromatography analysis on a 60 m X 0.25 mm i.d. capillary column coated with DB- 1 (non-polar), and programmed as follows: Two (2) min. isothermal at 100 degrees Celsius, then 10 degrees/min, to 250 degrees Celsius, where it is held for 10 minutes. A flame ionization detector is used for analysis. The retention times of disparlure on the DB-1 column with hydrogen carrier gas is given below. Other capillary columns of equivalent or better resolution may also give acceptable results. Compound Retention Time (Min.) • cis-7,8-epoxy-2-methyloctadecane +17.34 • trans-7,8-epoxy-2-methyloctadecane +17.21 The overall purity should be > 99% if the minor peaks whose area is less than 1% that of disparlure are ignored. 6. Optical rotation: a 25 +0.8/-. 0.2 (1 0% CC 1) Standards (+) Disparlure material shall meet the enantiomer purity and biological activity standards as described below to be accepted by the government. -- 1 of 7 -- Attachment 2 Enantiomer purity: • Based on measurements of intermediates; >99 (+) disparlure (cis-7,8-Epoxy-2- methyloctadecane) • Based on measurements using USDA analysis (Oliver & Waters, J. Chem. Ecology 21 (2), 199-211 [1995]; Oliver [2004], unpublished addendum to 1995 paper) • Based on USDA analysis contains less than 0.3% of the (-) isomer • The offeror shall submit with their offer the proposed method of synthesis along with the intended procedure for predicting the optical purity of the final product based on measured purity of the intermediates in the synthesis or the final product. Note – any confidential business information must be marked as such. a. Known published syntheses are: Iwaki, et al., J. Amer. Chem. Soc., 96, 7842 (1974) Mori, et al., Tetrahedron Letters, 17 (44) 3955 (1976) Farnum, et al., Tetrahedron Letters 18 (46), 4009 (1977) Mori et al., Tetrahedron 35 (7), 833 (1986) Mori, & Ebata, Tetrahedron Letter 42 (3), 313 (1988s) Satoh, et al., Tetrahedron Letter 29 (3), 313 (1988) Brevet & Mori, Synthesis 1992 (10), 1007 (1992) Keinan, et al., Tetrahedron Letters 33 (43), 6411 (1992) Mori, pp. 1-151 in: Total Synthesis Reference of Natural Products, Vol. 9 J. Ap Simon (ed.), John Wiley & Sons (1992; published online 2007). Product Evaluations The purity of the compound (pass or fail). The disparlure must be of the purity specified and the submitted sample must contain <0.3% (-)-disparlure. The contractor is required to submit samples of each production lot to the Government for chemical analysis and bioassay. After contract award, the contractor shall submit the following for each production lot prior to acceptance: • At least 250-mg sample of net (+) disparlure to the government from a previously untested lot* • Certificate of analysis • Safety Data Sheet • Description of the delivery lead time • Description of past performance • Written method of synthesis • Written information regarding the testing used to check quality and purity If the contractor is delivering more than one lot to meet contract requirements, then a 250-mg sample must be submitted from each lot for testing. -- 2 of 7 -- Attachment 2 *Lots are to be defined as: a product produced by continuous process; it is a specific identified amount produced in a unit of time or quantity in a manner that assures its having uniform character and quality. Product samples shall be shipped to: USDA-APHIS-PPQ-FPML ATTN: Allard Cosse 1398 W. Truck Rd. Buzzards Bay, MA 02542-1329 Phone: (508) 563-0985 All other information should be submitted to the Contracting Officer or their designated specialist. Upon award all product shipments must include: • Certificate of Analysis • Safety Data Sheet • Description of the delivery lead time • Written method of synthesis • Written information regarding product testing, quality, and purity: o Testing methods o Results of testing This information should be provided electronically to the individual placing the order. Packaging Must meet requirement to be reach the end destination intact and without damage. Also, the container shall be packaged in suitable cartons for shipment by common carriers. All shipping containers must be marked with: • Spongy Moth, Lymantria dispar lure • Quantity contained • Manufacture date • Expiration date • Contract # • Lot number The disparlure shall be packaged in quantities of 50 grams or less in each container. Each container must be labeled with the following information: • Company’s name • Spongy Moth, Lymantria dispar lure • Contract # • Manufacture date -- 3 of 7 -- Attachment 2 • Expiration date • Lot number Acceptance Received product will be tested chemically and biologically by the USDA Forest Pest Methods Laboratory in Buzzards Bay, MA. Chemical testing will allow conditional acceptance …