NO172983B - XANTATES AND ITS APPLICATION IN REGULATING PLANT GROWTH - Google Patents
XANTATES AND ITS APPLICATION IN REGULATING PLANT GROWTH Download PDFInfo
- Publication number
- NO172983B NO172983B NO901575A NO901575A NO172983B NO 172983 B NO172983 B NO 172983B NO 901575 A NO901575 A NO 901575A NO 901575 A NO901575 A NO 901575A NO 172983 B NO172983 B NO 172983B
- Authority
- NO
- Norway
- Prior art keywords
- xanthates
- xanthate
- growth
- plant
- dipropylene glycol
- Prior art date
Links
- 230000008635 plant growth Effects 0.000 title description 5
- 230000001105 regulatory effect Effects 0.000 title description 2
- 239000012991 xanthate Substances 0.000 claims description 43
- 241000196324 Embryophyta Species 0.000 claims description 30
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 claims description 17
- 229930002875 chlorophyll Natural products 0.000 claims description 11
- 235000019804 chlorophyll Nutrition 0.000 claims description 11
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 9
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 9
- 230000012010 growth Effects 0.000 claims description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 8
- 239000011591 potassium Chemical group 0.000 claims description 8
- 229910052700 potassium Inorganic materials 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical group OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 8
- KSUGAABGDUKBGT-UHFFFAOYSA-N carbonodithioic S,S-acid 2-(2-hydroxypropoxy)propan-1-ol Chemical group OC(=S)S.OC(=S)S.CC(COC(C)CO)O KSUGAABGDUKBGT-UHFFFAOYSA-N 0.000 claims description 7
- IDWGUSRAARELAE-UHFFFAOYSA-N carbonodithioic S,S-acid 2-[2-(2-hydroxyethoxy)ethoxy]ethanol Chemical group OC(=S)S.OC(=S)S.C(COCCOCCO)O IDWGUSRAARELAE-UHFFFAOYSA-N 0.000 claims description 7
- 244000207740 Lemna minor Species 0.000 claims description 6
- 239000000203 mixture Substances 0.000 description 23
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000006188 syrup Substances 0.000 description 9
- 235000020357 syrup Nutrition 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
- 239000012895 dilution Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 235000006439 Lemna minor Nutrition 0.000 description 4
- 235000001855 Portulaca oleracea Nutrition 0.000 description 3
- -1 aromatic hydroxy acids Chemical class 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000005648 plant growth regulator Substances 0.000 description 3
- 230000002786 root growth Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 239000007952 growth promoter Substances 0.000 description 2
- 150000001261 hydroxy acids Chemical class 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000003375 plant hormone Substances 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 230000000644 propagated effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 240000006541 Dactyloctenium aegyptium Species 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 101000993347 Gallus gallus Ciliary neurotrophic factor Proteins 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical class CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000009422 growth inhibiting effect Effects 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000026267 regulation of growth Effects 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Den foreliggende oppfinnelse vedrører nye xantater og anvendelser derav for å øke hastigheten av plantevekst og klorofyllkonsentrasjonen i planter. Derunder behandles planter med fortynnede løsninger av xantatene. The present invention relates to new xanthates and uses thereof to increase the rate of plant growth and the chlorophyll concentration in plants. Below that, plants are treated with diluted solutions of the xanthats.
Forskjellige derivater av organiske syrer er blitt fore-slått som plantevekstregulatorer. F.eks. beskriver vest-tysk patent 19 16 054 anvendelsen av alfa-hydroksy- eller alfa-ketoalkansyrer med 7-10 karbonatomer og deres derivater, spesielt amider, for å fremme veksten av planter under tørkebetingelser. US-patent 3 148 049 beskriver visse halogenerte ketosyrer, såsom halogenert acetoeddiksyre som plantevekstregulatorer. I 1970 rapporterte Mikami et al., Agr. Biol. Chem., 34, 977-979 forsøksresultater av en rekke hydroksysyrer som plantevekstregulatorer. Flere av disse, spesielt visse aromatiske hydroksysyrer, ble påvist å være rotvekstfremmende. Imidlertid forårsaket noen av disse enkle syrer, såsom glykolidsyre, snarere undertrykkelse av rotvekst enn fremming av rotvekst. Ingen av hydroksysyrene viste noen aktivitet i den anvendte rettvekst-fremming. US-patent 4 427 436 beskriver anvendelsen av et heterocyklisk xantat, etyl-3-benzothiazolinylmetylxantat, som inhibitor for veksten av soyabønner. Various derivatives of organic acids have been proposed as plant growth regulators. E.g. West German patent 19 16 054 describes the use of alpha-hydroxy or alpha-ketoalkanoic acids with 7-10 carbon atoms and their derivatives, especially amides, to promote the growth of plants under drought conditions. US Patent 3,148,049 discloses certain halogenated keto acids, such as halogenated acetoacetic acid, as plant growth regulators. In 1970, Mikami et al., Agr. Biol. Chem., 34, 977-979 experimental results of a number of hydroxy acids as plant growth regulators. Several of these, especially certain aromatic hydroxy acids, were shown to promote root growth. However, some of these simple acids, such as glycolic acid, caused suppression of root growth rather than promotion of root growth. None of the hydroxy acids showed any activity in the straight growth promoter used. US Patent 4,427,436 describes the use of a heterocyclic xanthate, ethyl 3-benzothiazolinyl methyl xanthate, as an inhibitor of soybean growth.
Det er nå overraskende funnet at visse xantater av glykoler virker som vekstfremmere og kan øke klorofyllkonsentrasjonen ved påføring på voksne planter. It has now surprisingly been found that certain xanthates of glycols act as growth promoters and can increase chlorophyll concentration when applied to adult plants.
Ifølge denne oppfinnelsen er xantatet valgt fra gruppen bestående av dipropylenglykolxantater med formelen According to this invention, the xanthate is selected from the group consisting of dipropylene glycol xanthates with the formula
hvor M er natrium eller kalium, dipropylenglykoldixantat med formelen hvor M er natrium eller kalium, trietylenglykolxantat med formelen hvor M er natrium eller kalium, eller trietylenglykoldixantat med formelen where M is sodium or potassium, dipropylene glycol dixanthate of the formula where M is sodium or potassium, triethylene glycol xanthate of the formula where M is sodium or potassium, or triethylene glycol dixanthate of the formula
hvor M er natrium eller kalium. where M is sodium or potassium.
Videre anvendes det ifølge denne oppfinnelse for å øke veksthastigheten av en plante ved at planten tilføres en effektiv mengde av ett eller flere xantater valgt fra denne gruppen. Furthermore, it is used according to this invention to increase the growth rate of a plant by supplying the plant with an effective amount of one or more xanthates selected from this group.
Ifølge denne oppfinnelse anvendes det også for å øke konsentrasjonen av klorofyll i en plante, ved at planten tilføres en effektiv mengde av ett eller flere xantater valgt fra denne gruppen. According to this invention, it is also used to increase the concentration of chlorophyll in a plant, by supplying the plant with an effective amount of one or more xanthates selected from this group.
Aktiviteten til xantatene som anvendes i denne oppfinnelsen, ble oppdaget når de ble prøvet i andegrassfremmingsmålingen til Mitchell og Livingston, "Methods of Studying Plant Hormones and Growth-Regulation Substances", USDA-ARS Agruculture Handbook, 336, s. 66-67 (1968). Dette forsøket viser at forskjellige xantater har vekstfremmende evner når de brukes i konsentrasjoner mellom 1 og 500 ppm (parts per million) på en vekt/volumbasis. Når xantatene var tilstede i konsentrasjoner på 0,1 ppm, ble ingen vekstøkning observert. Når på en annen side xantatene forelå i en konsentrasjon så høyt som 1000 ppm, ble vekstinhibering observert. For de prøvede xantater var den optimale vektsfremmingskonsentrasjon ca. 100 ppm. The activity of the xanthats used in this invention was discovered when tested in the andegrass promotion assay of Mitchell and Livingston, "Methods of Studying Plant Hormones and Growth-Regulation Substances", USDA-ARS Agriculture Handbook, 336, pp. 66-67 (1968 ). This experiment shows that various xanthats have growth promoting abilities when used in concentrations between 1 and 500 ppm (parts per million) on a weight/volume basis. When the xanthates were present at concentrations of 0.1 ppm, no growth enhancement was observed. On the other hand, when the xanthats were present at a concentration as high as 1000 ppm, growth inhibition was observed. For the tested xanthates, the optimal weight-promoting concentration was approx. 100 ppm.
En ytterligere fordel som ble oppnådd fra voksne planter i nærvær av xantater i denne oppfinnelsen, er at plantene akkumulerer mere klorofyll. Nærvær av slike xantater i vekstmediet, spesielt i konsentrasjoner på ca. 100 ppm på en vekt/volum-basis, øket sterkt mengden av klorofyll som ble akkulumert pr. mg plantevekt. A further advantage obtained from adult plants in the presence of xanthates in this invention is that the plants accumulate more chlorophyll. Presence of such xanthates in the growth medium, especially in concentrations of approx. 100 ppm on a weight/volume basis, greatly increased the amount of chlorophyll accumulated per mg plant weight.
Som angitt ovenfor, ble aktiviteten til xantatene som anvendes ifølge denne oppfinnelse oppdaget når de ble prøvet i andegrassfremmingsmålingen. Da denne målingen medfører dyrking av plantene på en vandig løsning, viser den anvendeligheten ved fremming av veksten til plantene i hydroponkultur. Likeledes er denne oppfinnelsen anvendelig når planter formeres ved hjelp av vekstkultur. Dette er en spesielt nyttig anvendelse av disse xantater, da mange planter nå formeres teknisk ved hjelp av vevskultur. As indicated above, the activity of the xanthats used in this invention was detected when tested in the duckweed promotion assay. As this measurement involves growing the plants in an aqueous solution, it shows the applicability of promoting the growth of the plants in hydroponic culture. Likewise, this invention is applicable when plants are propagated by means of growth culture. This is a particularly useful application of these xanthats, as many plants are now technically propagated by means of tissue culture.
De anvendte xantater i denne oppfinnelsen ses å produ-sere mer enn én vekstregulerende virkning på plantene. En spesielt vekstregulerende virkning plantene får avhenger selvfølgelig av en rekke variable, innbefattende xantatet eller blandingen av xantater som anvendes, konsentrasjonen og totale mengder av anvendte xantater, tidspunktet xantatene tilføres og typen planteart som behandles. Mengden av tilsatt materiale er en effektiv mengde som kreves for å oppnå den ønskede reaksjon. Generelt anvendes xantatene i fortynnede, vandige løsninger som inneholder xantatene i konsentrasjoner fra 1 til 500 ppm på en vekt/volum-basis. For de fleste formål er de foretrukne konsentrasjoner fra 10 ppm til 100 ppm. De best egnede konsentrasjoner for et spesielt formål er lette å bestemme ved velkjente utprøvningsforsøk, slik som dem som er gitt i eksemplene. The xanthates used in this invention are seen to produce more than one growth-regulating effect on the plants. A particularly growth-regulating effect the plants have depends of course on a number of variables, including the xanthate or mixture of xanthates used, the concentration and total amounts of xanthates used, the time the xanthates are added and the type of plant species being treated. The amount of material added is an effective amount required to achieve the desired reaction. In general, the xanthates are used in dilute, aqueous solutions containing the xanthates in concentrations from 1 to 500 ppm on a weight/volume basis. For most purposes, the preferred concentrations are from 10 ppm to 100 ppm. The most suitable concentrations for a particular purpose are readily determined by well-known assays such as those given in the Examples.
Løsninger av xantatene påføres lett plantene i vannet Solutions of the xanthates are easily applied to the plants in the water
som tilsettes for plantevekst. Dette vannet kan også inneholde nødvendige næringsmidler for plantene. Eventuelt kan løsninger av xantatene sprøytes på eller på annen måte tilføres røttene, stengelen, eller bladene til plantene. which is added for plant growth. This water can also contain necessary nutrients for the plants. Optionally, solutions of the xanthates can be sprayed on or otherwise supplied to the roots, stem or leaves of the plants.
De følgende spesifikke eksempler illustrerer den foreliggende oppfinnelse. De er ikke ment å begrense oppfinnelsen på noen måte. Når konsentrasjoner er gitt i ppm, er de på en vekt/volum-basis. Dipropylenglykolen som er anvendt som utgangsmateriale og for sammenligningsforsøk, fikk man fra Aldrich Chemical Company, Milwaukee, Wisconsin. Dietylen-glykolen som ble anvendt som utgangsmateriale, fikk man fra Union Carbide Corporation, New York City. Monoxantatene ble fremstilt ved langsom tilsetning av 1 mol karbondisulfid til en løsning av 1 mol av glykolen oppløst i en 50% vandig løsning inneholdende 1 mol kaliumhydroksyd. Blandingen ble avkjølt i is og rørt under tilsetningen. Etter tilsetningen fikk blandingen oppvarmes til romtemperatur under røring. De rå reaksjonsblandinger ble renset ved fortynning med 50 deler isopropylalkohol før blandingen ble filtrert, og moderluten ble konsentrert ved inndampning under redusert trykk ved 55"C. Løsningsmiddelrester ble fjernet fra blandingen ved ekstrak-sjon med eter og etylacetat. Det resterende xantat var en tung sirup. Dixantater av glykolene ble fremstilt på lignende måte som anvendes for monoxantatene, bortsett fra 2 mol kaliumhydroksyd og 2 mol karbondisulfid ble brukt pr. mol glykol. Tilstedeværelsen av xantatgruppen i hver av forbindelsene ble vist ved C<13> NMR-analyse. The following specific examples illustrate the present invention. They are not intended to limit the invention in any way. When concentrations are given in ppm, they are on a weight/volume basis. The dipropylene glycol used as starting material and for comparative experiments was obtained from Aldrich Chemical Company, Milwaukee, Wisconsin. The diethylene glycol used as starting material was obtained from Union Carbide Corporation, New York City. The monoxanthates were prepared by slowly adding 1 mole of carbon disulfide to a solution of 1 mole of the glycol dissolved in a 50% aqueous solution containing 1 mole of potassium hydroxide. The mixture was cooled in ice and stirred during the addition. After the addition, the mixture was allowed to warm to room temperature while stirring. The crude reaction mixtures were purified by dilution with 50 parts of isopropyl alcohol before the mixture was filtered, and the mother liquor was concentrated by evaporation under reduced pressure at 55°C. Solvent residues were removed from the mixture by extraction with ether and ethyl acetate. The remaining xanthate was a heavy syrup. Dixanthates of the glycols were prepared in a manner similar to that used for the monoxanthates, except 2 moles of potassium hydroxide and 2 moles of carbon disulfide were used per mole of glycol. The presence of the xanthate group in each compound was shown by C<13> NMR analysis.
Dipropylenglykol xantat ble fremstilt ved langsomt å tilsette et mol karbondisulfid til en løsning av et mol dipropylenglykol oppløst i en 50% vandig løsning inneholdende et mol kaliumhydroksyd. Blandingen ble avkjølt i is og rørt under tilsetningen. Etter tilsetningen fikk blandingen oppvarmes til romtemperatur i 1 time under røring. Den rå reaksjonsblanding ble renset ved fortynning med 50 deler isopropylalkohol før blandingen ble filtrert, og moderluten ble konsentrert ved fordampning under redusert trykk ved 55°C. Løsningsmiddelresten ble fjernet fra blandingen ved ekstrak-sjon med eter og etylacetat. Dipropylenglykol xantatresten var en tykk sirup. Tilstedeværelsen av dipropylenglykol xantat i den tykke sirup ble bekreftet ved C<13> NMR analyse. Dipropylene glycol xanthate was prepared by slowly adding one mole of carbon disulfide to a solution of one mole of dipropylene glycol dissolved in a 50% aqueous solution containing one mole of potassium hydroxide. The mixture was cooled in ice and stirred during the addition. After the addition, the mixture was allowed to warm to room temperature for 1 hour while stirring. The crude reaction mixture was purified by dilution with 50 parts of isopropyl alcohol before the mixture was filtered, and the mother liquor was concentrated by evaporation under reduced pressure at 55°C. The solvent residue was removed from the mixture by extraction with ether and ethyl acetate. The dipropylene glycol xanthate residue was a thick syrup. The presence of dipropylene glycol xanthate in the thick syrup was confirmed by C<13> NMR analysis.
Dipropylenglykol dixantat ble fremstilt ved langsomt å tilsette 2 mol karbondisulfid til en løsning av 1 mol dipropylenglykol oppløst i en 50% vandig løsning inneholdende 2 mol kaliumhydroksyd. Blandingen ble avkjølt i is og rørt under tilsetningen. Etter tilsetningen fikk blandingen oppvarmes til romtemperatur i 1 time under røring. Den rå reaksjonsblanding ble renset ved fortynning med 50 deler isopropylalkohol før blandingen ble filtrert, og moderluten ble konsentrert ved fordampning under redusert trykk ved 55°C. Løsningsmiddelresten ble fjernet fra blandingen ved ekstrak-sjon med eter og etylacetat. Dipropylenglykol dixantatresten var en tykk sirup. Tilstedeværelsen av dipropylenglykol dixantat i den tykke sirup ble bekreftet ved C<13> NMR analyse. Dipropylene glycol dixanthate was prepared by slowly adding 2 moles of carbon disulfide to a solution of 1 mole of dipropylene glycol dissolved in a 50% aqueous solution containing 2 moles of potassium hydroxide. The mixture was cooled in ice and stirred during the addition. After the addition, the mixture was allowed to warm to room temperature for 1 hour while stirring. The crude reaction mixture was purified by dilution with 50 parts of isopropyl alcohol before the mixture was filtered, and the mother liquor was concentrated by evaporation under reduced pressure at 55°C. The solvent residue was removed from the mixture by extraction with ether and ethyl acetate. The dipropylene glycol dixanthate residue was a thick syrup. The presence of dipropylene glycol dixanthate in the thick syrup was confirmed by C<13> NMR analysis.
Trietylenglykol xantat ble fremstilt ved langsomt å tilsette 1 mol karbondisulfid til en løsning av 1 mol trietylenglykol oppløst i en 50% vandig løsning inneholdende 1 mol kaliumhydroksyd. Blandingen ble avkjølt i is og rørt under tilsetningen. Etter tilsetningen fikk blandingen oppvarmes til romtemperatur i 1 time under røring. Den rå reaksjonsblanding ble renset ved fortynning med 50 deler isopropylalkohol før blandingen ble filtrert, og moderluten ble konsentrert ved fordampning under redusert trykk ved 55°C. Løsningsmiddelresten ble fjernet fra blandingen ved ekstrak-sjon med eter og etylacetat. Trietylenglykol xantatresten var en tykk sirup. Tilstedeværelsen av trietylenglykol xantat i den tykke sirup ble bekreftet ved C<13> NMR analyse. Triethylene glycol xanthate was prepared by slowly adding 1 mole of carbon disulfide to a solution of 1 mole of triethylene glycol dissolved in a 50% aqueous solution containing 1 mole of potassium hydroxide. The mixture was cooled in ice and stirred during the addition. After the addition, the mixture was allowed to warm to room temperature for 1 hour while stirring. The crude reaction mixture was purified by dilution with 50 parts of isopropyl alcohol before the mixture was filtered, and the mother liquor was concentrated by evaporation under reduced pressure at 55°C. The solvent residue was removed from the mixture by extraction with ether and ethyl acetate. The triethylene glycol xanthate residue was a thick syrup. The presence of triethylene glycol xanthate in the thick syrup was confirmed by C<13> NMR analysis.
Trietylenglykol dixantat ble fremstilt ved langsomt å tilsette 2 mol karbondisulfid til en løsning av 1 mol trietylenglykol oppløst i en 50% vandig løsning inneholdende 2 mol kaliumhydroksyd. Blandingen ble avkjølt i is og rørt under tilsetningen. Etter tilsetningen fikk blandingen oppvarmes til romtemperatur i 1 time under røring. Den rå reaksjonsblanding ble renset ved fortynning med 50 deler isopropylalkohol før blandingen ble filtrert, og moderluten ble konsentrert ved fordampning under redusert trykk ved 55°C. Løsningsmiddelresten ble fjernet fra blandingen ved ekstrak-sjon med eter og etylacetat. Trietylenglykol dixantatresten var en tykk sirup. Tilstedeværelsen av trietylenglykol dixantat i den tykke sirup ble bekreftet ved C<13> NMR analyse. Triethylene glycol dixanthate was prepared by slowly adding 2 moles of carbon disulfide to a solution of 1 mole of triethylene glycol dissolved in a 50% aqueous solution containing 2 moles of potassium hydroxide. The mixture was cooled in ice and stirred during the addition. After the addition, the mixture was allowed to warm to room temperature for 1 hour while stirring. The crude reaction mixture was purified by dilution with 50 parts of isopropyl alcohol before the mixture was filtered, and the mother liquor was concentrated by evaporation under reduced pressure at 55°C. The solvent residue was removed from the mixture by extraction with ether and ethyl acetate. The triethylene glycol dixanthate residue was a thick syrup. The presence of triethylene glycol dixanthate in the thick syrup was confirmed by C<13> NMR analysis.
Eksempel 1 Example 1
Andegrass (Lemna minor L.) ble dyrket etter den generelle fremgangsmåten til Mitchell og Livingston, "Metods of Studying Plant Hormones and Growth Regulating Substances", USDA-ARS Agruculture Handbook, 336, s. 66-67 (1968). Plantene ble dyrket på Nickells medium som beskrevet i håndboken, idet jern var tilstede som jern(II)ion chelatert med EDTA. Én plante på 3-blads stadiet ble plassert i hver kolbe. Kolbene ble inkubert ved 25°C i 16-18 timer under 300- til 500-fot lys i 16 timer pr. dag. Plantene ble høstet og tørket før plante-vekten ble målt. Alle rapporterte verdier representerer 3-5 Duckgrass (Lemna minor L.) was grown according to the general procedure of Mitchell and Livingston, "Methods of Studying Plant Hormones and Growth Regulating Substances", USDA-ARS Agroculture Handbook, 336, pp. 66-67 (1968). The plants were grown on Nickell's medium as described in the manual, iron being present as iron(II) ion chelated with EDTA. One plant at the 3-leaf stage was placed in each flask. The flasks were incubated at 25°C for 16-18 hours under 300- to 500-foot light for 16 hours per day. The plants were harvested and dried before the plant weight was measured. All reported values represent 3-5
replikater. replicates.
Eksperimenter ble utført, hvori forskjellige konsentrasjoner av xantater ble satt til andegrassvekstmediet. En kontroll ble kjørt, hvori det ikke var tilsatt noe xantat. Resultatene som er gitt i tabell 1 viser at veksten økes sterkt når forholdsvis små konsentrasjoner av xantatene er tilstede i mediet. Høyere konsentrasjoner av xantatene viser en vekstinhiberende virkning. Experiments were conducted in which different concentrations of xanthates were added to the duckweed growth medium. A control was run in which no xanthate was added. The results given in table 1 show that growth is strongly increased when relatively small concentrations of the xanthates are present in the medium. Higher concentrations of the xanthates show a growth-inhibiting effect.
Sammenligningsforsøket viser også at en utgangsglykol, hvorfra xantatene ble fremstilt, ikke viser noen vekstfremmende aktivitet ved de prøvede konsentrasjoner. The comparison test also shows that a starting glycol, from which the xanthats were produced, does not show any growth-promoting activity at the tested concentrations.
Eksempel 2 Example 2
Den generelle fremgangsmåte fra eksempel 1 ble fulgt, og klorofyllinnholdet i de høstete planter ble bestemt ved metoden til Kirk, "Planta", 78, 200-207 (1968). Prøver av det forveide, tørkete andegrass ble oppslemmet i 80% aceton. Blandingen ble homogenisert i 3 0 sekunder ved bruk av en POLYTRON® Brand Homogenizer (Brinkman Instruments, Westbury, New York). Blandingen ble sentrifugert og absorpsjonen til supernatanten ble avlest ved 663 og 645 nm. Fra disse avlesninger ble antallet mikrogram klorofyll pr. mg tørrvekt bestemt ved bruk av nomogrammet til Kirk. Resultatene som er gitt i tabell II viser at xantatene som brukes i fremgangsmåten i denne oppfinnelsen øker plantenes klorofyllinnhold. Økningen i klorofyllinnhold bemerkes spesielt når xantatene foreligger i vekstmediet i en konsentrasjon på ca. 100 ppm. The general procedure of Example 1 was followed and the chlorophyll content of the harvested plants was determined by the method of Kirk, "Planta", 78, 200-207 (1968). Samples of the preweighed, dried duckweed were slurried in 80% acetone. The mixture was homogenized for 30 seconds using a POLYTRON® Brand Homogenizer (Brinkman Instruments, Westbury, New York). The mixture was centrifuged and the absorbance of the supernatant was read at 663 and 645 nm. From these readings, the number of micrograms of chlorophyll per mg dry weight determined using Kirk's nomogram. The results given in Table II show that the xanthats used in the method of this invention increase the plants' chlorophyll content. The increase in chlorophyll content is particularly noticeable when the xanthates are present in the growth medium in a concentration of approx. 100 ppm.
Således er det åpenbart at ifølge oppfinnelsen tilveie-bringes en forbedret fremgangsmåte for å øke planteveksthastigheten og for å øke klorofyllinnholdet til planter som fullstendig tilfredsstiller hensiktene, målene og fordelene som er beskrevet ovenfor. Når oppfinnelsen er blitt beskrevet i forbindelse med spesielle utførelsesformer derav, er det klart at mange alternativer, modifikasjoner og variasjoner vil være åpenbare for en fagmann på området i lys av den fore-gående beskrivelse. Oppfinnelsestanken er uttrykt i de etterfølgende krav. Thus, it is obvious that according to the invention an improved method is provided for increasing the plant growth rate and for increasing the chlorophyll content of plants which fully satisfy the purposes, objectives and advantages described above. When the invention has been described in connection with particular embodiments thereof, it is clear that many alternatives, modifications and variations will be obvious to a person skilled in the art in light of the foregoing description. The inventive idea is expressed in the following claims.
Claims (8)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/105,936 US4806149A (en) | 1987-10-08 | 1987-10-08 | Method for regulating plant growth using xanthates |
PCT/US1988/003441 WO1989003383A1 (en) | 1987-10-08 | 1988-10-06 | Method for regulating plant growth using xanthates |
Publications (4)
Publication Number | Publication Date |
---|---|
NO901575D0 NO901575D0 (en) | 1990-04-06 |
NO901575L NO901575L (en) | 1990-05-11 |
NO172983B true NO172983B (en) | 1993-06-28 |
NO172983C NO172983C (en) | 1993-10-06 |
Family
ID=26777876
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO901575A NO172983C (en) | 1987-10-08 | 1990-04-06 | XANTATES AND ITS APPLICATION IN REGULATING PLANT GROWTH |
Country Status (1)
Country | Link |
---|---|
NO (1) | NO172983C (en) |
-
1990
- 1990-04-06 NO NO901575A patent/NO172983C/en unknown
Also Published As
Publication number | Publication date |
---|---|
NO172983C (en) | 1993-10-06 |
NO901575D0 (en) | 1990-04-06 |
NO901575L (en) | 1990-05-11 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4799953A (en) | Method for regulating plant growth using sulfur-containing organic acids | |
NO172983B (en) | XANTATES AND ITS APPLICATION IN REGULATING PLANT GROWTH | |
Gaspar et al. | Citrus leaf abscission. Regulatory role of exogenous auxin and ethylene on peroxidases and endogenous growth substances | |
Krotkov et al. | Utilization of acetate by tobacco leaves, as determined with C14 | |
US4806149A (en) | Method for regulating plant growth using xanthates | |
IL35659A (en) | 9-azolylfluorene-9-carboxylic acid derivatives,their production and their use for the regulation of plant growth | |
US3985539A (en) | 4,5-Dihalopyrrole-2-carbonitrile-containing terrestrial and aquatic hebicidal composition | |
Yoshikawa et al. | Synthesis and biological activity of benzaldehyde O-alkyloximes as abscisic acid mimics (Part 1) | |
Göring et al. | Proline accumulation induced by weak acids and IAA in coleoptiles of wheat seedlings | |
GB2135315A (en) | Hexanor-brassinolide-22-ethers having a plant growth-regulating action and their manufacture and use | |
SU1318160A3 (en) | Method for producing 1,2,3-thiadiazol-3-in-5-ilideneurea derivatives or acid-additive salts thereof with hydrochloric acid | |
NO172982B (en) | SULFUR, ORGANIC ACIDS AND USE THEREOF | |
US4505736A (en) | N-Phosphonomethylglycine derivatives and use as herbicides | |
EP0576116B1 (en) | Physiologically active substances of plant, process for the preparation thereof, and utilities thereof | |
GB2127022A (en) | 28-Methyl-brassinosteroid derivatives having a plant growth- regulating action and their manufacture and use | |
JP2004051485A (en) | Agricultural use antimicrobial agent/fungicide comprising cinnamic acid derivative as active ingredient | |
YosHIKAWA et al. | Synthesis and biological activities of isocoumarins | |
US2937187A (en) | Nu, nu'-di(phthalidyl-3) derivatives of aromatic diamines | |
CN116589419A (en) | 2-phenoxy-2- (1H-1, 2, 4-triazole) -acetophenone compound and preparation method and application thereof | |
JPS5874658A (en) | Novel bactericidal n-phenylalaninate homologues, manufacture and use | |
GB2127021A (en) | Brassinosteroid derivatives having a plant growth-regulating action and their manufacture and use | |
JPS58113107A (en) | Herbicide | |
CN113264836A (en) | Preparation and application of (7S) -11-methoxy-3, 7, 11-trimethyl-2, 4-ethyl dodecenoate | |
吉川博道 et al. | Synthesis and Biological Activities of Isocoumarins | |
JPH01113388A (en) | Herbicidal composition |