1-Methylcyclopropene

Synthesis

The compound 1-methylcyclopropene is synthesized by the reaction of methallyl chloride and phenyllithium, which functions as a base:

The phenyllithium should be free of lithium halides. The corresponding reaction of allyl chloride and phenyllithium main affords cyclopropylbenzene.

Isomers

Methylcyclopropene can refer to either of two isomers: 1-methylcyclopropene, which is covered in this article, or 3-methylcyclopropene which is not. Of note is that the name '2-methylcyclopropene' would not be a correct name for 1-methylcyclopropene. Also of note is that the compound methylcyclopropane is yet a different chemical compound, specifically a cycloalkane with the formula .

Mechanism of action

Ethylene is a gas acting at trace levels (typically between a few tenths and a few thousands ppm in the gas atmosphere) throughout the life of a plant by stimulating or regulating various processes such as the ripening of climacteric fruit, the opening of flowers (dehiscence process), and the shedding of leaves (abscission process). The mechanism of action of 1-MCP involves its tightly binding to the ethylene receptor in plants, thereby blocking the effects of ethylene (competitive inhibitor).

Commercial use

The compound 1-MCP is used commercially to maintain the freshness of ornamental plants and flowers and preventing the ripening of fruits. It is used in enclosed sites, such as coolers, truck trailers, greenhouses, storage facilities, and shipping containers.

Under the brand name EthylBloc, 1-MCP was approved in by the U.S. Environmental Protection Agency for use on ornamental crops. For cut flowers, potted flowers, and bedding, nursery and foliage plants, 1-MCP prevents or delays wilting, leaf yellowing, opening, and death.

Under the brand name SmartFresh, 1-MCP is used in the agriculture industry by growers, packers, and shippers to prevent or delay the natural ripening process. The use of 1-MCP in agricultural products including apples, kiwifruit, tomatoes, bananas, plums, persimmons, avocados, and melons has been approved and accepted for use in more than 34 countries including the European Union and the United States. Although benefiting from fresher produce and lower cost, the consumer however may be purchasing fruit that is older than expected.

The compound 1-MCP is also being developed as a crop protection technique. By spraying 1-MCP on growing field crops during times of stress, the crops may be protected from moderate heat and drought conditions.

References

References

1. [https://patents.google.com/patent/US6017849 Daly James and Kourelis Bob, January 25, 2000. Synthesis methods, complexes and delivery methods for the safe and convenient storage, transport and application of compounds for inhibiting the ethylene response in plants. US Patent 6,017,849.]
2. (April 2003). "1-Methylcyclopropene: a review". Postharvest Biology and Technology.
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7. (1995). "Inhibition of ethylene-induced cellular senescence symptoms by 1-methylcyclopropene, a new inhibitor of ethylene action". Physiol. Plant..
8. Sisler E.C., Serek M.. (2003). "Compounds interacting with the ethylene receptor in plants". Plant Biol.
9. [https://web.archive.org/web/20030202061457/http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_224459.htm 1-Methylcyclopropene Fact Sheet], [[U.S. Environmental Protection Agency]]
10. Jim Daly. (2001). "EthylBloc — An Industry Perspective". Perishables Handling Quarterly.
11. [http://www.agrofresh.com/ethylbloc.html What is EthylBloc technology?] {{Webarchive. link. (2008-01-30 , at agrofresh.com)
12. [http://www.floralife.com/industry_professionals/our_products/ethylbloc.asp EthylBloc Ethylene Inhibitor] {{Webarchive. link. (2009-01-22 , at floralife.com)
13. [http://www.agrofresh.com/smartfresh.html SmartFresh Quality System] {{Webarchive. link. (2008-02-11 at agrofresh.com)
14. link. (2007-03-14 , by Leah Vyse, December 13, 2005.)
15. [http://farmindustrynews.com/crop-protection/0118-syngenta-agrofresh-alliance/ Syngenta-Agrofresh Alliance: New crop protection technology takes aim at row crops] {{Webarchive. link. (2008-06-26 , ''Farm Industry News'', Jan 18, 2008)