UNITED STATES ENVIRONMENTAL PROTECTI ON AGENCY WASHI NGTON, D.C. 20460
OFFICE OF PREVENTION, PESTICIDES AND TOXIC SUBSTANCES

May 2 0 , 2009

MEMORANDUM S UBJECT : Amendment to the New Oilseed Crop Group 20 ( 40 C FR § 180.41 (c) to

Add Calendula ( Calendula officinali s L. ) as a New Member of the C rop Group for ChemSAC Review

. MRID 467896

- 01

.
FROM : Bernard A. Schneider, Ph.D., Senior Plant Physiologist

Chemistry

and Exposure Branch Health Effects Division (7509P ) THROUGH : William Donovan, Ph.D. , C hairperson

HED Chemistry

Science Advisory

Council (ChemSAC) Health Effects Division (7509P) Jennifer Selwy

n, PMRA Rame Cromwell, FEAD (750 6P )

TO : Barbara Madden, Minor Use Officer

Risk Integration, Minor Use, and Emergency Response Branch (RIMUERB) Registration Division (7505P)

BACKGROUND AND RECOMMENDATIONS : It was brought to our attention in the USDA IR

- 4 ChemSAC Proposal for S

Metolachlor and Diquat Bromide Use in Calendu la officinalis for Nonfood Use Seed2

Production, May

5, 2009 that Calendula would be an appropriate crop to add to the ChemSAC approved Oilseed crop group 20 (January 12, 2007). The Federal Register Notice is being prepared to codify the Oilseed crop group. The timing is optimal for a pproving Calendula to be a member of the Oilseed crop group. The oilseed crop group not only will provide a benefit to our growers but also provides commodities that not only have beneficial edible food and feed items, nutritional and medicinal uses, cosm etic and industrial uses in paints, etc but an opportunity to develop oilseeds as biofuels to benefit U.S. and Canada alternatives to fossil fuels. I will discuss the Calendula crop and why I recommend that it would be a good addition to the Oilseed crop group. I have added information from Kathry n Homa’s well documented report and references, and input and documents from Neal Boughton, Director of Agronomy for Technology Crops Ltd., based in Winston

- Salem, North Carolina . In addition references from th e USDA Agricola and CRIS database are included. Also a separate presentation modified from Neal Boughton is provided in a separate PowerPoint presentation. HED Recommendation for Proposal to Add Calendula to the Oilseed Crop Group: I recommend ChemSA C concur to add Calendula to the Oilseed Crop Group and the Sunflower subgroup 20

- 09B based on its similarities in cultural practices, geographical location, pest problems, oil uses , and similarities to other members of the oilseed group

.
ABBREVIATED ANALYSIS:

BOTANICAL CHARACTERISTICS OF PROPOSED COMMODIT Y : Calendula is an annual flower that originated in southern Europe and the Eastern Mediterranean area. Currently , this plant is widely grown in the United States mostly as an o rnamental flower an d is grown in USDA Plant hardiness zones 2

– 9. Calendula is a member of the Asteraceae famil y which includes the following oilseeds: S

unflower, safflower, stokes aster, Niger seed, and v ernonia

. The exposure of the crop to pesticides would be simi lar to sunflower, since the flowers and seed heads are exposed. The other members of the Sunflower subgroup 20B are based on whether the seeds are partiall y exposed to pesticides applied during the growing season. The members of this subgroup include: C astor oil plant , Chinese tallowtree , Euphorbia , Evening primrose , Jojoba , Niger seed , Rose hip , Safflower , Stokes aster, Sunflower, Tallowwood , Tea oil plant , and Vernonia

. Utilization of all these oilseed crops is similar in that they are grown for th eir oil, seed and meal. Calendula has potential for industrial uses and for edible refined oil. For3

now most of the work is being conducted on Calendula as a replacement for tung oil which is a paint additive.

GROWTH AND DEVELOPMENT OF CALENDULA Calendula growth stages are very similar to the sunflower (See Table 4 Selected Growth Stages of Sunflower Using BBCH Identification Codes in Schneider, B. A. 2007. Crop Grouping Part IV Oilseed Crop Group Anal ysis, MRID 467896

- 01, January 8). Day s to first flower vary

from 50

– 75 day s. Flowering starts middle of June and flowers vary from 1.5

– 3.5 cm. Flowers may be orange or yellow. The p lant reaches 40 to 85 cm tall during the season . The seeds will ripen in earl y August with harvesting from August 1

– 15. In Canada research trials in prairie areas had calendula flowering at 51

– 75 day s and maturing at 144 days and mean seed yields of 216 kg/ha and harvesting from August

– earl y September

. Average calendic acid content of the seed is 45

– 50 % un der dryland conditions.

GEOGRAPHICAL DISRTIBUTION OF CALENDULA: Calendula is widely

adapted to areas of the U.S since it has ornamental uses and has been grown for many ye ars . It has been widel y research and developed as an industrial oilseed in many European countries, funded b y National Governments and the European Union, to support and develop new oil crop species. Canada has also researched this crop and it is being grown in Montana and Canada . Requirement limiting oilseed production is being ne ar an oilseed processing facility

. Due to the success of Calendula in Europe, contract production of Calendula is beginning in the United States and Canada. Currently , Technology

Crops Ltd , a company

that contracts the growing of many specialty oil crops including high oleic sunflowers and high erucic acid rapeseed, is looking to contract the production of Calendula in the state of Minnesota.

CALENDULA CULTURAL PRACTICES AND CROP ROTATIONS : Calendula should be planted when soil temperatures are > 46 ° F and the s eed s germinate rapidly . It can be planted as part of a no

- till or conventional till system at 1⁄2

- 3⁄4 inch deep and row widths similar to cereals with 6

– 7 plants per sq. ft. Seeds are planted with a grain drill at rate of 7

– 12 kg/ha and a plant population of 40

– 60 plants/m3. The rows are 12

– 25 cm wide but can vary up to 50 cm. The soil needs to be a sandy l oam to m edium c lays s oil with the following climatic factors: Average minimum temperature 45

- 55 F

Average maximum temperat ure 60

- 76 F Average rainfall of 1 1/2 to 2 inches/month Calendula has a higher frost tolerance than flax.4

CROP ROTATION S YSTEMS : Calendula can be in a crop rotation system with cereals grains, so yb eans, or fallow. CALENDULA PEST PROBLEMS : Very simil ar to other oilseed members of the Asteraceae family including annual grasses and broadleaf weeds that reduce yi elds and prevent proper growth and can contribute to seed contamination at harvest. Plant diseases such as powdery mildew, Botry tis and Sclerotinia are a problem as well as aster yellows. Insects such moth larvae ( Heliothis ) , cabbage loppers, and blister beetles have sometimes been a problem as well as the soy bean cy st nematode. CALENDULA HARVESTING AND PROCESSING: Another major constraint in maximizing Calendula oilseed production occurs at harvest time. Due to variations in Calendula seed maturity , harvesting for oilseed production is quite difficult. Many growers face a situation where some seeds have reached maturity, while other seeds r emain immature. Waiting for all seeds in the field to dry can lead to seed shedding and a significant reduction in yield. In order to harvest the oilseed properl y, the use of a desiccant prior to combining was shown to result in less seed loss compared to windrowing. Use of a desiccant may solve the harvesting problems. Like all oilseeds it needs to be stored at 9 % moisture

. Yields may vary from 0.7

– 9 T/ha at 91 % DM and oil percent will vary from 14.2

– 19.2%. The crop needs to be swathed at present due to lack of chemical desiccant approvals when 80 % of seed heads are brown and with a combine. Mechanical harvesting is used for all the oilseed crops including calendula, none are hand harvested, and grain combines are adapted to planting and harve sting. COMPARISON OF POTENTIAL RESIDUE LEVELS: Magness, Markle, and Compton in 1971 classified food and feed crops based on predicting the potential for pesticide residues based on exposure of the edible parts to applied pesticides , which led to the dev elopment of the crop groups. The oilseeds were classified in the Edible Food Oil Crop Category I and II. Category Iand II includes the food oil crops in which the source of oil is the seeds. Category Iinclude oilseeds that have the seed protected in a pod like canola. Category I I oil crops have the seeds partially exposed during development and include sunflower and safflower, and calendula is similar to this category , so all would be members of the Sunflower subgroup 20B with sunflower as the representative commodity . One would expect pesticide residues to be similar in most of the members of the oilseed crop group, and distinct oilseed crop subgroups may be based on potential of residue to be deposited on the seed.5

CALENDULA OIL USES: Calendula oil can be used for medicinal purpose, dyes, and food purposes including garnishes, butters, flavorings and colorings, and it has recently gained popularity

as an oilseed crop for industrial use. Research in the last ten years in Europe has shown that calendula offers the most immediate prospect of commercialization of many oilseeds and can be used in a number of valuable non

- food use products including paints, coatings and some industrial nylon products. It can also be used as a replacement for Tung oil which has to be imported and is expensive and getting harder to obtain. Calendula oil, which makes up 40 to 46% of the seed, contains 50

- 55% highl y conjugated calendic acid (octadeca

- 8,10:12

- trienoic acid) and 28

- 30% non

- conjugated linoenic acid. It has been discovered that the calendic fatty acid in this plant is the “most rapidly oxidized fatty

acid known in nature and has an extensive number of applications in the plastics, paints and coatings industries” Tung oil, which contains high levels of poly unsaturated fatty acids, currentl y serves as the reactive component in fast drying paints. Used widel y in Europe in paints and inks, “5,000 tons of tung oil is imported annually into the UK from China and South America at prices between $1,200 and $2, 300” Ithas been found that Calendula oil may be able to replace the “erratic” supply of tung oil in the future. Calendula is also important in the oil

- based paint industry , as it is a “diluents of white spirit, the volatile drying component that may so on be limited by legislation as it releases volatile organic compounds into the atmosphere” Replacing these harmful compounds in paints and inks with calendula oil

- based paints can result in less ground

- level ozone levels and smog

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OTHER HED CONSIDERA TIONS FOR CALEND ULA :
CHANGES TO EPA DATABASES: The proposed new Oilseed Crop Group 20 will affect the need to update many Risk Assessment Models, Residue Chemistry Guidelines, OPP databases, and/or HED Standard Operating Procedures (SOP).

HED SOP 2000 .1

– “ Guidance for Translation of Field Trial Data from Representative Commodities in the Crop Group Regulation to Other Commodities in Each Crop Group/Subgroup” issued September 12, 2000. There is no guidance in the SOP for the new Oilseed crop group, so the following guidance for translation of the representative commodities to other members of the subgroup will be provided below: The proposed new translations of field trials from the representative commodities to other commoditie s in the Sunflower subgroup 20B would be as follows:6

Crop Subgroup 20B: Sunflower subgroup Representative Commodity : Sunflower SUBGROUP COMMODITY REPRESENTATIVE COMMODITY Calendula Sunflower Castor oil plant Sunflower Chinese tallowtree Sun flower Euphorbia Sunflower Evening primrose Sunflower Jojoba Sunflower Niger seed Sunflower Rose hip Sunflower Safflower Sunflower Stokes aster Sunflower Sunflower Sunflower T allowwood Sunflower Tea oil plant Sunflower Vernoni a Sunflower

________________________________________________________________________ (5) H ealth Effects Division Dry Matter and Seeding Rate Database for the Oilseed Crop Group, prepared by

Dr’s. NG and B. A. Schneider , June 2006, are shown in Table 2 4 below: Health Effects Division Dry Matter and Seeding Rate Database. Oilseed Crop Group. Prepared b y Dr’s. NG and B. A. Schneider. June 2006

. Commodity % Dry Matter Calendula, seed 91.0 Rapeseed, seed 90.0, 91.0, 92.0 Rapeseed, meal 88.0, 90. 0 Rapeseed, forage 30.0 Safflower, seed 93.0, 94.0, 94.3 Safflower, meal 91.0, 92.0 Safflower, refined oil 0.0 Sunflower, seed 93.0, 95.0 Sunflower, meal 92.0 Sunflower, refined oil 0.07

CODEX CLASSIFICATION OF PROPOSED COMMODITIES AND EPA FOOD AND FEED COMMODITY VOCABULARY: Calendula is not in the Oilseed crop group for Codex. The I CGCC will submit calendula to be added to the Codex crop 23

. Codex has marigold flowers HH 737 herbs and spices same scientific names . The US also has the same scientific name for marigold in the Herb and Spice group 19. The genus Tagetes contains most of the marigolds used for its petals in poultry

feed. The oilseed Calendula will not be used for poultry feed.

TOLERANCE EXPRESSION GUIDANCE :
Until the Federal Register Notice is issued revising the Crop Group Regulation to establish the new Oilseed Crop Group 20 with three Crop subgroups the commodities approved for the crop group and subgroups will have to be listed as separate commodities at the same tolerance level. This also applied to the new Crop subgroups, the individual commodities will have to be listed separately with each at the same tolerance level. The ChemSAC approved crop group is sent to the Risk Integration, Minor Use, and Emergency

Respons e Branch (RIMUERB) of the Registration Division can immediately implement the new Crop Group and Crop Subgroups with new tolerance expressions located in the Section F submissions

. The tolerance expression examples will provide an expedited way

to establi sh tolerances in or on oilseed crops, especially for new reduced risk pesticides, without requiring additional residue data for all the crops noted. This will create a practice in the United States which is already formalized in Canada and promote international harmonization. Several tolerance expression examples for guidance purposes for use b y RIM UERB and HED reviewers will be listed below:

Example 1 : How will the Crop group and subgroups appear in the Federal Register for the proposed crop group re gulation [40CFR 180.41(c)]? This example is for the Field and External Affairs Division (FEAD) use in preparing the new Federal Register Regulation. The example follows the same format as the current Crop Grouping Regulation Federal Register Notice (FR 6 0, No.95, 5/17/95, 26626

- 26643). Answer to Example 1 : “Crop Group 20 : Oilseed Crop Group. (i) Representative commodities. Rapeseed, canola varieties onl y; sunflower, and cottonseed, undelinted seed. (ii) Table. The following Table 1 lists all the commodities listed in Crop Group 20 and identifies the related crop subgroups and includes cultivars , hy brids , and /or varieties of these commodities

.8

TABLE 1

- Crop Group 20 : Oilseed Crop Group Commodities Related crop subgroups Borage , Borago officinalis (L

. ) 20A Calendula, Calendula officinalis L. 20B Castor oil plant , Ricinus communis (L.) 20B Chinese tallowtree , Triadica sebifera (L.) Small 20B Cottonseed , Gossypium spp.L

. 20C Crambe, Crambe hispanica L. ; Crambe abyssinica Hochst. ex R.E. Fr. 20A Cuphea, Cuphea hyssopifolia Kunth 20A Echium, Echium plantagine um L 20A Euphorbia, Euphorbia esula L. 20B Evening primrose , Oenothera biennis (L.) 20B Flax seed, Linum usitatissimum L. 20A Gold of p leasure , Camelina sativa L. Crantz 20A H are's ear mustard , Conringia orientalis Dumort. 20A Jojoba, Simmo n dsia chinensis (Link) C.K. Schneid

. 20B Lesquerella, Lesquerella recurvata (Engelm. ex A. Gray) S. Watson 20A Lunaria, Lunaria annua L. 20A Meadowfoam, Limnanthes alba Hartw. Ex Benth. 20A Milkweed, Ascle

pias spp. L

. 20A Mustard seed , Brassica hirta , spp. 20A Niger seed, Guizotia abyssinica (L .f.) Cass. 20B O il radish , Raphanus sativus var. oleiformis Pers 20A Poppy seed, Papaver somniferum L. s ub sp. somniferum 20A Rap e seed , Brassica spp.; Brassica na pus L. 20A Rose hip , Rosa rubiginosa L. 20B Safflower , Carthamus tinctorious L. 20B Sesame, Sesamum indicum L. ; Sesamum radiatum Schumach. & Thonn. 20A Stokes aster, Stokesia laevis (Hill) Greene 20B Sunflower , Helianthus annuus L. 20B S weet rocket , Hesperis matronalis L. 20A T allowwood , Ximenia americana L. 20B Tea oil plant, Camellia oleifera C. Abel 20B Vernonia, Vernonia galamensis (Cass.) Less. 20B (iii) Table. The following Table 2 identifies the crop subgroups for Crop Group 20 , specifies the r epresentative commodities for each subgroup and lists all the commodities included in each subgroup. TABLE 2

- Crop Group 20: Subgroup Listing9

Representative commodities Commodities S ubgroup 20 A: Rapeseed subgroup. Rapeseed, canola varieties only. Borag e , Crambe , Cuphea , Echium, Flax seed , Gold of pleasure , Hare's ear mustard , Lesquerella , Lunaria, Meadowfoam , Milkweed, Mustard seed , Oil radish , Poppy seed , Rapeseed, Sesame, Sweet rocket, cultivars and/or hybrids of these. S ubgroup 20 B: Sunflower. Sun flower. Calendula , Castor oil plant , Chinese tallowtree , Euphorbia , Evening primrose/common , Jo

joba , Niger seed , Rose hip , Safflower , Stokes aster, Sunflower, Tallowwood , Tea oil plant , Vernonia

. S ubgroup 20 C: Cottonseed subgroup. Cotton, undelinted seed

. Cottonseed

Example 2 : How will Iexpress the tolerances on an interim basis until the Federal Register Notice is final for the Oilseed crop group 20, fo r example at a tolerance level of 1.5 ppm? This example will be useful for the Registration Divisi on (RD) and Health Effects Division (HED) to prepare tolerance tables. A ll the new proposed commodities will have to be listed separately from the crop group tolerance and at the same level as the crop group

. Answer to Example 2 : Commodity Parts per mil lion (ppm) Borage , seed 1.5 Calendula, seed 1.5 Castor oil plant , seed 1.5 Chinese tallowtree, seed 1.5 Cotton, undelinted seed 1.5 Crambe, seed 1.5 Cuphea, seed 1.5 Echium, seed 1.5 Euphorbia, seed 1.5 Evening primrose, seed 1.5 Flax, seed 1 .5 Gold of p leasure , seed 1.5 H are's ear mustard , seed 1.5 Jojoba, seed 1.5 Lesquerella, seed 1.5 Lunaria, seed 1.5 Meadowfoam, seed 1.5 Milkweed, seed 1.5 Mustard, seed 1.5 Niger seed, seed 1.5 Oil radish, seed 1.510

Commodity Parts per mil lion (ppm) Poppy , seed 1.5 Rapeseed, se ed 1.5 Rose hip, seed 1.5 Safflower, seed 1.5 Sesame, seed 1.5 Stokes aster, seed 1.5 Sunflower, seed 1.5 Sweet rocket, seed 1.5 Tallowwood, seed 1.5 Tea oil plant, seed 1.5 Vernonia, seed 1.5 Cultivars , varieties, and/or hy brids of those above c ommodities Example 3 : How will Iexpress the tolerances on an interim basis until the Federal Register Notice is final for the Sunflower subgroup 20B, for example at a tolerance level of 1.5 ppm? This example will be useful for the Registration Divisio n (RD) and Health Effects Division (HED) to prepare tolerance tables. Answer to Example 3 for the Sunflower subgroup 20B: Commodity Parts per million (ppm) Calendula, seed 1.5 Castor oil plant, seed 1.5 Chinese tallowtree, seed 1.5 Euphorbia, seed 1 .5 Evening primrose, seed 1.5 Jojoba, seed 1.5 Niger seed, seed 1.5 Rose hip, seed 1.5 Safflower, seed 1.5 Stokes aster, seed 1.5 Sunflower, seed 1.5 Tallowwood, seed 1.5 Tea oil plant, seed 1.5 Vernonia, seed 1.5 Cultivars , varieties, and/or hyb rids of those above commodities

REFERENCES : USDA CRIS PROJECTS: 1. PROJ NO: ND03500. 2008. INVESTIGATOR: Johnson, B. L.11

PERFORMING INSTITUTION: PLANT SCIENCES NORTH DAKOTA STATE UNIV FARGO, NORTH DAKOTA 58105 PRODUCTION PRACTICES FOR SUNFLOWER, ALTERNATIVE, AND NEW AGRONOMIC AND HORTICULTURAL CROPS Producers will benefit from improved production practices that generate higher yields and greater profits. This will be realized with sunflower, alternative, and new agronomic and horticultural crops grown in North Dakota and the northern Great Plains.

2. PROJ NO: ND06346 2005. INVESTIGATOR: Halvorson, M. PERFORMING INSTITUTION: NORTH CENTRAL RESEARCH EXTENSION CTR NORTH DAKOTA STATE UNIV FARGO, NORTH DAKOTA 58105 CROP MANAGEMENT PRACTICES FOR UNIQUE OILSEED AND LEGUME CROPS FOR THE NC REGION OF NORTH DAKOTA NON

- TECHNICAL SUMMARY: No information on best management practices for ne w alternative crops and soybeans exists for this area of North Dakota. This project will determine the best seeding dates for borage, camelina, and calendula . We will also determine the best row spacing, seeding rate, and tillage system for soybean production in western North Dakota. OBJECTIVES: Determine the effects of seeding date on character expression and perform ance of borage, calendula , and camelina in North Dakota. Determine the effect of swathing time on seed shatter and yield of borage. Determine the effect of row spacing, population and tillage system on the performance of soy beans. APPROACH: Will research five seeding dates to determine the best seeding date for borage, camelina, and calendula . The seeding dates will range from May 1 to June 15

3. PROJ NO: MONB00804 . 2007. INVESTIGATOR: Callan, N. W. PERFORMING INSTITUTION: WESTERN AGRI RES CENTER MON TA NA STATE UNIVERSITY BOZEMAN, MONTANA 59717 HORTICULTURAL CROP PRODUCTION Many small

- to
- medium sized Montana agricultural producers are turning to high

- value essential oil crops and medicinal and culinary herbs to diversify their farming operations and increase income in the face of declining returns for traditional commodities. There is currently little information available regarding cultural practices for specialty crops grown in Montana's climate. The purpose of this research is to provide agricultural producers with information about production practices for specialty crops in Montana. Biological plant disease control is emphasized.12

Other References: 1. Homa, Kathryn. 2009. IR

- 4 ChemSAC Proposal: S

- Metolachlor and Diquat Dibromide Use in Calendula officinalis for Non

- food Use Seed Production. USDA IR

- 4. May. 2. Froment, M., D. Masterbroek, and K. Van Gorp. 2008. A Growers Manual for Calendula officinalis L. 9pp. ADAS Bridge Research Centre, UK, Wetherlund Royal CEBECO Group Plant Research Institute. Netherlands. 3. Rose, J. 2009. Aromatic Plant Project. San Francisco, CA. (http://www.aromaticplantproject.com/marigold). 4. Kalvatcher, Z., R. W alder, and D. Gazaro. 1997. Anti HI V extracts from Calendula officinalis. Biomedical & Pharmaco therapy 51(4). 5. Calendula 2009. http://www.ienica.net/crops/calendula.htm 6. Re, T., D. Moony, E. Antignac, E. Dufour, I. Bark, V. Srinivasan, and G. Nohynek. 2009. Food and Chemistry In Press. 7. Dyer, T., S. Stymer, A. Green, and A. Carlson. 2008. High Value Oils from Plants. Plant J. 54(4): 640

- 655. 8. Okoh, O., A. Sadienenho, and A. Afolayon. 2007. The Effect of Age on Yield and Composition of the Essential Oils. Calendula officinalis. J. Applied Sciences. 7(23): 3806

- 3010 9. S inkard, A., R. Wilen, B. Barl, and M. Bandara. 2001. Evaluation of Calendula s an Industrial Oilseed Crop. University of Saskatchewan Agricultural Development Fund Final Report 19980314. ADF Project 98000314

- Res.65 BW. 16 pp. 10. Van Soest, L. 1993. New Crop Development in Europe. Pages 30

– 38 In J. Janick and J. Simon. New Crops> Wiley, NY. 11. Schumacher, J. 2006. Montana Oilseed Markets: Hi storical Price and Production Statistics. Agricultural Marketing Policy Paper No. 19. Montana State University November. 12. Richter, C. 2007. Commercial calendula Cultivation. Aromatic Plant Project. San Francisco, CA. 13. Dyer, J. and R. Mullen. 2005. Development and Potential of Genetically Engineered Oilseeds. Seed Science Research 15: 255

- 267. 14. Dyer, J. and R. Mullen. 2008. Engineering Plant Oils as High value Industrial Feedstocks for Biorefining the Need for Underpinning Cell Biology Research. Phy siologia Planatarum 132: 11

- 22.