Progress 10/01/09 to 09/30/10
Outputs
OUTPUTS: The work has been published and patented and several oral presentations have been presented One of the problems found is that the synthetic procedure being used is not very effective (low yield) This is an important aspect for the use of these compouhnnds and it is being modified.This has been a major effort at this time. PARTICIPANTS: Dr Margrethe Serek, Ludovic Segilie, Heiko Mibus Of the Facylty of Natural Sciences, Institute for Ornimentals and Woody Plant Science Leibiz University of Hanover Germany did some testing of the compounds and presented papers at meetings. TARGET AUDIENCES: Not relevant to this project. PROJECT MODIFICATIONS: Not relevant to this project.
Impacts
The work being done will extend the range of the available ethylene action inhibitors to include outdoor treatments. These compounds as salts are not volatile thus they can be used as sprays.The parent compound (1-methylcyclopropene}must be used in an enclosed location because it is very volatile and would rapidly be lost.
Publications
- E.C.Sisler,L Seglie, H Mibus and Serek, M. 2010 Non-Volatile Derivative of 1_MCP Prevents Ethylene Responses in Ornamentals Acta. Hort.ISHS 880:311-315.
- Edward C. Sisler, Ludovica Seglie, Heiko Mibus, and Margrethe Serek, 2010,Preventing Ethylene Responces in Topical Crops. In Press.
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Progress 10/01/08 to 09/30/09
Outputs
OUTPUTS: PROGRESS: Outputs The evaluation of inhibitors of ethylene action has continued. These inhibitors can be used in the gas phase and also as the salt formed with a weak acid such as carbonic acid. Most of the studies have been done with N, N-dipropyl (1-cyclopropenylmethyl) amine or as the salt of the compound with a weak acid. Some of the plants tested were Rosa hyrida L., Dianthus caryophyllus L. Pelagonium zonal and Phalaenopsis Lila. All of these flowers were much improved the useful life and quality of the compound. In addition other compounds are being developed for use as inhibitors of the ethylene receptor. Among these are 3- pyrrolidine (1-cyclopropenylmethyl) amine and N, N-methyl, butyl (1-cyclopropenylmethyl) amine and their non-volatile salts for testing on various plants and plant parts. PARTICIPANTS: Not relevant to this project. TARGET AUDIENCES: Not relevant to this project. PROJECT MODIFICATIONS: Not relevant to this project.
Impacts
IMPACT: The production and testing of these compounds should be of value in extending the life of such things of flowers, altering fruit sets to advantage and to control other ethylene responses, Overall, the use of these compounds make it possible to turn ethylene responses on with ethylene and turn them off both in confined spaces with volatile 1-methylcyclopropene (1-MCP) and also outdoors with these newer compounds. Potential compounds to be converted to cyclopropenes and tested. 2-bromo 3-(pyrrolidineamino)propene 2-bromo-3-(N-methyl-N-butylamine)propene.
Publications
- No publications reported this period
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Progress 10/01/07 to 09/30/08
Outputs
OUTPUTS: Work has continued on cylopropenes inhibitors of ethylene action compounds which may be active as a gas or also in a non-volatile form. Plants parts such as flowers and leaves have been tested. These parts are thin and it should be possible to inactivate the receptor in either by the compounds as a gas or as a salt made from the compounds as a gas or as a salt made from acids such as acetic or carbonic acid. Flowers of plants tested were Petunia , Impatiens and the wild species Krigia dandelion which is related to the common dandelion flowers . All of these were protected by the gas and also water solution of the salt applied as a spray or used as a dip.' The shelf life of the flowers were extended several days longer when treated as compared to untreated flowers when exposed to ethylene. These experiments show that ethylene effects can be controlled in a large range of conditions both indoors and outdoors. PARTICIPANTS: Nothing significant to report during this reporting period. TARGET AUDIENCES: Nothing significant to report during this reporting period. PROJECT MODIFICATIONS: Nothing significant to report during this reporting period.
Impacts
Use of cycopropene compounds is now well known which extend the shelf life of fruits and vegetables in closed systems. Now this has been extended to outdoor uses. It now seems possible to develop other uses for these compounds. Ethylene controls many responces in plants and this may take a lot of different forms. When plants are injured, many produce wound ethylene. This may cause loss in yields and quality. These experiments may lead to control of these losses.
Publications
- Sisler, E. C. 2008 1-Alkenes:Ethylene action compounds or competitive inhibitors of ethylene in plants. Plant Science 175:145-148.
- Apelbaum A, Sisler E. C, Feng X, and Goren R 2008. Assessment of the potency of 1-substituted cyclopropenes to counteract ethylene-induced processes in plants. Plant Growth Regulation Plant Growth Regulation 55:101-113
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Progress 10/01/06 to 09/30/07
Outputs
Work continued on the development of cyclopropene compounds that can be applied as a salt to bananas. The reason for using bananas was that they can be easily obtained and are usually of good quality. Work on this project was in cooperation with a group in Israel on a BARD Grant. The application of the compounds in the US was with the salts of a nitrogen compound which requires an acid to form the salt. The Israeli group used a cyclopropene having an acid group attached and the salt was used with a base giving the salt. A number of acids were tested, all of which were somewhat successful. Weak acids consisted of acetic, formic,carbonic (formed from CO2) and phosphoric acid. Longer organic acids have a very obnoxious odor and were not tested. Hydrochloric acid was also tested some but care must be used since the compounds are not stable to strong acids. Tests were done by painting the salts of the compounds on banana peels. The mixture contained a wetting agent (usually
Tween 20), water, and the salt. Various amounts were used and after the painting the solution had dried they were exposed to ethylene after 24 hours had elapsed from the time of painting. The minimum amount of compound was recorded. It was much more than was required as a gas, and the compound only protected the peel. In practice, the plant material would not be exposed to ethylene after 24 hours(which ends the treatment time), and could remain on the plant material for many days thus extending the treatment time and penetration time. This has not yet been done. If the plant material were not treated with ethylene after 24 hours and the compounds were allowed to remain without ethylene a more realistic assessment of the method should be obtained.
Impacts
Cyclopropene compounds extend the life of fruits and vegetables and counteract other ethylene responses. To date only 1-MCP (1-methylcyclopropene) is commercially available. It is a volatile compound which means it must be used in an enclosure. The present research overcomes this shortcoming. The use as a spray or dip means it can in be used outdoors to do things like improve fruit set and counteract other ethylene responses outdoors. Although the process has been demonstrated using bananas, the practical use of these salts of cyclopropenes on other ethylene sensitive processes remains to be tested.
Publications
- Buanong,M. Heiko Mibus, Edward C. Sisler and Margrethe Serek 2007 Effect of 1-decylcyclopropene in improvement of the display life of Kalochanche (kalanchanchoe blossfeldiana Poelln.) Flowers. Acta Hort 755:409-413.
- Mibus H., M. Buanong, E.C. Sisler and M. Serek, 2007. New inhibitors of ethylene perception in improvement of display quality in miniature roses (Rosa hybrida L.). In: Advances in Plant Ethylene Research, eds. A. Ramina, C. Chang, J. Giovannoni, H. Klee, P. Perata and E. Woltering. Proceedings of the 7th International Symposium on the Plant Hormone Ethylene. Springer ISBN 978-1-4020-6013-7: 15-20
- Serek, M, Sisler, E. C., Woltering, E. J., Mibus, H. 2007 Chemical and Molecular Strategies to block ethylene perception for increased Flower life Proc on Quality Management Supply Chains Eds. S. Kanlayanarat et al. Acta Hort. 755:163-167
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Progress 10/01/05 to 09/30/06
Outputs
Work has continued on compounds to block the ethylene receptor Selection and characterization of compounds that could be used as sprays, and other outdoor situations. Compounds that could be applied either a gas or as the salt were tested. N,N-dialkyl (cyclopropenylmethyl)amine compounds were tested.Dimethyl, diethyl, dipropyl, and dibutyl compounds were prepared and tested for the minimum concentration needed and the time of protection against ethylene were given by the compound. Bananas were used as the major test material. The minimum amount required decreased from the dimethyl to dipropyl compound then increased considerably with dibutyl compound. This probably was due to the decrease in vapor pressure and diffusion caused by the increased weight. N-(1-methylcyclopropene)-aniline was also tested but required a high amount. All of the compounds protected the bananas peel for 26 days and the inner flesh for about 33 days. When the compounds were applied to bananas
as a water solution with a swab they protected for several days. Application was for 24 hours, and then ethylene was applied. Protection required higher amounts than when applied as a gas and was largely restricted to the peel. This probably was due to a lower diffusion rate. If the compounds were allowed more time, they probably would have protected at a lower level. The application of compounds to the peel was used as an assay system to determine the potency of different compounds.
Impacts
These results should provide additional parameters to develop compounds that will interact the ethylene receptor and prevent or delay ethylene responses. They should be applicable under a lot of different conditions and thus make the use of ethylene inhibitors practical while previous compounds were not because of their volatility..
Publications
- Serek, M. Sisler, EC Frello, S and Sirskandarajah 2006 Postharvest technology for extending the shelf life of ornamentals crops. Int.Jour of Postharvest Technology and Innovation 1:69-75. :
- Sisler EC, Grichko VP Serek M 2006 Compounds interacting with the ethylene receptor- agonists and antagonists. In Ethylene Action in Plants (NA Khan, Ed) Springer-Verlag pp 1-34.
- Sisler, EC 2006 The discovery and development of compounds counteracting ethylene at the receptor level. Biotechnology Advances 24:357-367.
- Serek, M. Woltering. EJ Sisler, EC, Frello, S and Sriskandarjah, S. 2006. Controlling ethylene responses in flowers at the receptor lrvr; Biotechnology Advances 24:368-381.
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Progress 10/01/04 to 09/30/05
Outputs
Progress: 2004/10 to 2005/10 During the year, work continued on the BARD Project and additional compounds were prepared and assayed in a banana assay. This was an assay done in the vapor state for the compounds They were them shipped to Israel for further assay and testing. During this period compounds containing a nitrogen compound were explored and the effect of structure was noted. Compounds such as N-(1-cyclopropenylmethyl}aniline and N,N-Di (1-Cyclopentylmethyl)amine were tested. The series N,N-Dimethyl(1-cyclopropenylmethyl)amine N,N-Diethyl(1-cyclopropenylmethyl)amine, and N,N-Dipropyl(1-cyclopropenylmethyl)amine were tested. The results of this study indicated the compounds such as the aniline derivative was less active than the others. The compounds that were disubstituted were more active and the longer the chain , the higher the activity. This is thought to be a hydrophobic effect with longer chain compounds being more hydrophobic which causes the compound
to bind to the receptor more rapidly. The final analysis of these compounds effectiveness in a spray will depend on the results
Impacts
: These results should provide additional parameters to develop compounds that will interact the ethylene receptor and prevent or delay ethylene responses. They should be applicable under a lot of different conditions and thus make the use of ethylene inhibitors practical while previous compounds were not because of their volatility..
Publications
- Serek, M. Sisler, E.C. Frello, S and Sirskandarajah. 2005 Postharvest technology for extending the shelf-life of ornamentals flowers.(International Conference on Postharvest Technology and Quality Management in Arid Tropics (Oman Jordon) Book of Abstracts 6.
- Publications: Saleh S. Grichko, V.P Sisler, EC and Glick, BR 2004 The effect of 1-cyclopropenyl butyl ether on early plant growth Jour Plant Growth Reg. (23:307-312.
- Serek, M. Muller, R. and Sisler, EC 2005 Jakosc sadzonek Rosliny Ozdobne 1:13.
- Sisler, EC Z Kebenei T Winkelmann and M. Serek 2005 Efficacy of new inhibitors of ethylene preception in improvement of display life of ornamental crops. 8th International Symposium Postharvest Physiology of Ornamental Plants. 10-14 08 2003, Holland. Acta Horticulture 669:315-319.
- Buanong M. Mibus, H, Sisler, E C and Serek, M. 2005. Efficacy of new inhibitors of perception in improvement of display quality of miniature potted roses (Rosa hybrida L. Plant Growth Regulation 47:29-38.)
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Progress 10/01/03 to 09/30/04
Outputs
Progress has continued on preparing and testing compound which interact with the ethylene rceptor. Many compounds that can be applied as a gas have already been reported. Recently an effort has been made to discover and prepare compounds that can be applied as a spray or related means of application such as a vase or in soil. The basic stradegy here id to apply compounds that can be converted into a salt for application and could again become the free compound inside the tissue. Organic acids would likely serve in this capacity. They could be applied as for example Na+, K+, or NH+4 salts Amino compounds could be applied as the hydrochloride salt. Amino compounds could be applied as the hydrochloride salt. Some compounds have been made and applied in the gaseous form to determine their relative activity. 3-cycloprop-1-enyl-prop1noic acid, and N-(1-cyclopropenylmethyl)ethylamine has been applied as a gas using banana fruits as an assay. Although some of the compounds
act at higher than desired levels, others are being tested, and it is felt some of the compounds will be in the desired range.
Impacts
Impact: These results should make it possible to develop ethylene receptor blocking (inhibitor)compounds to control ethylene responses under a lot of different conditions such as treating plants or plant parts with non-volatile compounds either above ground or underground.It should reduce spoilage an well as help to control yields
Publications
- Kebenei, Z, Sisler, E. C. Winklemann, T. and Serek, M (2003) Effect of 1-methycyclopropene and 1-octylcyclopropene on vase life of sweet pea (lathyrus odoratusL.) flowers. Jour. of Hort, Science and Biotech. 78-433-436.
- Grichko, V. Sisler, E.C. and Serek M. (2003) Anti-ethylene properties of monoterpenes and some other naturally occurring compounds in plants. SAAS Bulletin:Biochemestry and Biotechnology .16:20-27.
- Feng,X Apelbaum, A. Sisler,E. C. and Goren, R. (2004) Control of ethylene activity in various plant systems by structural analogs of 1-methylcyclopropene. Plant Growth Reg. 42:29-38.
- Serek M., E.C. Sisler and Muller, R.(2003) Nowy srodek przerlazajacy trwalosc, warzwy i kwiatow. Haslo ogrodnicze 4(2004):11-13
- Sisler, E.C. and M. Serek, (2003). Manipulating ethylene effects in horticultural crops by 1 MCP and related receptor blocking compounds. 2nd International Congress of Plant Physiology on sustainable plant productivity under changing environment, 1-8.2003, New Delhi, India. Indian Journal for Plant Physiology. Indian J. Plant Physiol. (special issue): 451-455
- Serek, M. Sisler, E. C. Winkelmann, T. and Kebenei, Z. (2004). Neue Inhibitoren der Ethgyleeneaufnahme. Das TASPO Magzin 2:24-26.
- Sisler, E.C. and M. Serek, (2003). Manipulating ethylene effects in horticultural crops by 1 MCP and related receptor blocking compounds. 2nd International Congress of Plant Physiology on sustainable plant productivity under changing environment, 1-8.2003, New Delhi, India. Indian Journal for Plant Physiology. Indian J. Plant Physiol. (special issue): 451-455
- Serek, M Sisler EC Frello, S. Sriskandarajah S. (2004) Stratagie per il miglioramento della vita plante ornamentali Italus Hortus 11:55-58
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Progress 10/01/02 to 09/30/03
Outputs
Work has continued on preparing compounds for inactivating the ethylene receptor and preventing ethylene responses. A BARD Grant which compliments this program was funded effective 10/1/2003. During this work, most of the chemical synthesis is done in the US and most of the testing is done in Israel. Work was started on preparing these compounds . In particular, compounds which could could be applied as sprays or otherwise applied to plants in vases and soil were sought. 1-(3-Hydroxylpropyl)-cyclopropene ,1 (2-Hydroxylethyl)-cyclopropene, N-(1 cyclopropenylmethyl)butyl-amine and 3-cycloprop-enyl-propanoic acid and its isopropylamine salt were tested and shown to be active in protecting banana fruits against ethylene. Likewise 1-cyclopropenemethyl hexyl ester was shown to be active. Most of these compounds protected for about 25 days, but the iisopropyl amine salt of 3-cycloprop-enyl-propanoic acid only protected for 16 days. The reason is unknown.Also a 24 hour
exposure to 1-cyclopropenemethyl hexyl ester did not protect bananas against ethylene if exposed to ethylene immediately after the 24 hour exposure, but became insensitive after standing an additional hours. Probably this was because at the end of the 24 hours, the cyclopropene had not yet inactivated the receptor, but after 48 hours without further treatment it had inactivated it. These compounds are being used as models for studying the parameters foractivity to produce other more versatile compounds, Some of these compounds have been supplied to the Israeli group to develop the techniques for utilizing the compounds in protecting plants against ethylene.
Impacts
Impact: These results should make it possible to develop ethylene receptor blocking (inhibitor)compounds to control ethylene responses under a lot of different conditions such as treating plants or plant parts with non-volatile compounds either above ground or underground.
Publications
- Sisler E.C. Goren R. and Serek, M. (2002) Probes for the ethylene receptor and antagonists for ethylene action. SAAS Bulletin:Biochemestry and Biotechnology 15:16-24.
- Serek, M., E.C. Sisler and M.S. Reid. (2002) Use of EthylBloc (1-MCP) to increase the life of ethylene-sensitive cut flowers and potted plants. Post-raccola e qualita delle produzioni florovivaistiche mediterranee, 24.11.2001, Napoli,Italy. Atti N. 21: 29-34.
- Sisler, E. C. and Serek M. (2003) Compounds interacting with the ethylene receptor in plants Plant Biology:5:473-480.
- Sisler, E. C , Goren, R. Abelbaum A. and Serek, M. (2003) 1-Substituted cyclopropenes: Effective blocking agents for the ethylene receptor in plants. Plant Growth Reg. 40:223-228.
- Kebenei, Z, Sisler, EC, Winkelmann, T. and Serek, M. (2003) Efficacy of inhibitors of ethylene perception in improvement of display life of kalanchoe (Kalanchoe blossfeldiana Poell.) flowers. Plant Biology and Technology 30:169-176.
- Sisler, E. C. (2002) Methods of blocking an ethylene response in plants using derivatives. United States Patent 6,365, 549 B2.
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Progress 10/01/01 to 09/30/02
Outputs
Work has proceeded along previous lines of work on ethylene receptor inhibitors. Some new compounds have been prepared, and testing is in progress. Some work has done on exploring the parameters for preparing new compounds. To do this compounds commercially available (alkenes) were used. These require continuous exposure but do give which compounds can interact with the receptor. It was found that compounds such as allylbenzene , 4-phenyl-1-butene and 2-vinylnaphthalene were active. Many monoterpenes were active. Other natural occuring compounds such as cinnamaldehyde, estragole, and eugenol were active inhibitors of the ethylene response. Both cis-2-hexene-1-ol and trans-2-hexene-1-ol were active. These experiments demonstrate that many more compounds are active than previously thought possible. This information will be used in preparing new compounds.
Impacts
These studies may make it possible to use a lot of different types of inhibitors for the control of ethylene responses. and make it possible to apply them in more ways.
Publications
- Serek, M. and Sisler, E. C. and Frello,S. (2002) Nyt Holdbarhedsmiddel. Garten Tidende 40:20
- Sisler, E. C. and Serek, M. (2002) Cyclopropenes interacting with ethylene binding sites. Technich postraccolta dei prodotti orthoflorofruiticoli pp27-28
- Serek, M. and Sisler, E. C. and Winkelmann (2002)Zulassung in Deutschland fur 2004 erwartet De GA Deutscher Gartenbau 44:40-41.
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