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WO1994015467A1 - Utilisation de composes pour conferer aux plantes une tolerance aux basses temperatures - Google Patents

Utilisation de composes pour conferer aux plantes une tolerance aux basses temperatures Download PDF

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WO1994015467A1
WO1994015467A1 PCT/CA1994/000005 CA9400005W WO9415467A1 WO 1994015467 A1 WO1994015467 A1 WO 1994015467A1 CA 9400005 W CA9400005 W CA 9400005W WO 9415467 A1 WO9415467 A1 WO 9415467A1
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loweralkyl
oxo
thio
hydroxy
halogen
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Suzanne R. Abrams
Lawrence V. Gusta
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National Research Council of Canada
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    • C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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Definitions

  • the invention generally relates to conferring low temperature tolerance to plants.
  • the invention includes the use of compounds in agricultural compositions to be applied to plants in the field to enhance their overall freezing resistance and/or chilling tolerance.
  • Brassica and native trees require a growth period at low temperatures (0 to 10°C) to trigger the appropriate genes involved in acclimation to freezing stresses. During this period of cold acclimation, numerous biochemical, physiological and metabolic functions are altered in plants.
  • the freezing tolerance of tissue cultures can be enhanced by treating cultures with abscisic acid.
  • abscisic acid for example, bromegrass cell suspension cultures treated with 75 ⁇ M ABA for 7 days can withstand freezing to -40°C (Reaney and Gusta 1987, Plant Physiol., 83:423).
  • results on whole plants are conflicting in that ABA can increase, decrease or have no effect on freezing tolerance.
  • chilling injury usually occurs between the temperature range of 17 to 0°C. It is distinguished from frost injury which occurs at subzero temperatures and involves the crystallization of water.
  • frost injury which occurs at subzero temperatures and involves the crystallization of water.
  • One of the first indications of chilling injury is wilting of the plant but the temperature at which chilling occurs at depends on both the species and cultivar.
  • cultivated crops such as tomato and beans are sensitive to temperatures below 17°C. As a result of exposure to these low temperatures, growth is inhibited which results in a delay in flowering, fruiting and maturity. Often flower seeds abort, seed set is reduced and the quality of the product is often unacceptable in the market place.
  • Daie et al. ((1981) J. Am. Hortic. 106:11-13) and Daie and Campbell ((1981) Plant Physiol. 67:26-28) examined the effect of low temperature (above 0°C) on ABA accumulation in chilling-sensitive plant species. They found that chilling sensitive species exhibited higher levels of ABA when exposed to 10°C. It has repeatedly been shown that exogenous ABA protects plants against a chilling stress (see for example Rikin et al. (1976), Bot. Gaz. 137:307-312; Bowman and Jansson (1980), Physiol. Plant 56:207-212; Eamus and Wilson (1983), J. Exp. Bot. 34:1000-1006 and Eamus (1986), J. Exp. Bot.
  • ABA at concentrations as low as 10 -8 M acts as an antitranspirant in partially closing stomata (N. Kondo, I. Maruta and K. Sugahara, 1980, Plant Cell. Physiol., 21:817).
  • Stomata may remain partially closed for as long as 4 days after treatment with 10 -4 M ABA and an acetylenic ABA aldehyde analog (H. Schaudolf, 1987, J. Plant Physiol., 131:433). This analog decreases water use in Helianthus annuus. Triticum aestivum and Lycopersicon esculentum while maintaining yield.
  • abscisic acid is expensive to produce commercially and secondly, the desired effect is only observed for short periods of time beause ABA, a naturally occurring hormone, is rapidly degraded by microorganisms found on the plants or by the plants themselves.
  • the present invention first relates to a composition for enhancing low temperature tolerance in plants which comprises an effective amount of at least one compound having the following formula (I) :
  • R is carboxyl, aldehyde, hydroxy, hydroxyloweralkyl, alkoxyloweralkyl, loweralkoxycarbonyl, loweracyloxy- loweralkyl, acetylloweralkyl, loweralkanoyl, loweralkylamino, diloweralkylamino, loweralkoxy, loweracyloxy, loweralkylthio, loweralkyl sulphonyl, loweralkyl sulphinyl, amino, carbonyl, halogen, thio, phosphate, sulfoxide, sulfone, deuterium or cycloalkyl or cycloalkoxy having from 4 to 6 carbon atoms which is optionally sbustituted by loweralkyl, halogen, oxygen, hydroxy or loweralkoxy;
  • R 1 is loweralkyl, hydrogen, oxo, hydroxyloweralkyl, loweralkoxy, halogen, thio, sulfoxide, sulfone, phosphate or deuterium;
  • R 2 is hydrogen, oxo, hydroxy, halogen, thio, phosphate, sulfoxide, sulfone or deuterium;
  • R 3 is oxo, thio, carboxyl, aldehyde, loweralkyl, hydroxyloweralkyl, alkoxyloweralkyl, loweralkoxycarbonyl, loweracyloxyloweralkyl, acetylloweralkyl, loweralkanoyl, loweralkylamino, diloweralkylamino, loweralkoxy, loweracyloxy, loweralkylthio, loweralkylhalide, loweralkyldeuterium, loweralkyl sulphonyl, loweralkyl sulphinyl, or carbonyl;
  • R 2 when R 2 is oxo or thio, R 2 may be linked to both C 1 and C 2 carbon atoms to form an epoxy or a thioepoxy ring;
  • R 4 is hydrogen, oxo, halogen, thio, phosphate, sulfoxide, sulfone, deuterium, hydroxy, loweralkylsiloxane, carboxyl, aldehyde, hydroxyloweralkyl, alkoxyloweralkyl, lower- alkoxycarbonyl, loweracyloxyloweralkyl, acetylloweralkyl, loweralkanoyl, loweralkylamino, diloweralkylamino, loweralkoxy, loweracyloxy, loweralkylthio, loweralkyl sulphonyl, loweralkyl sulphinyl, amino, carbonyl, cycloalkyl or cycloalkoxy having from 4 to 6 carbon atoms which is optionally substituted by loweralkyl, halogen
  • R 4 when R 4 is oxo or thio, R 4 may be linked to the carbon atom adjacent to R 5 to form an epoxy or thioepoxy ring;
  • R 5 is carboxyl, hydroxy, aldehyde, hydroxyloweralkyl, alkoxyloweralkyl, loweralkoxycarbonyl, loweracyloxyloweralkyl, acetylloweralkyl, acetoxyloweralkyl, loweralkanoyl, loweralkylamino, diloweralkylamino, loweralkoxy, loweracyloxy, loweralkylthio, loweralkyl sulphonyl, loweralkyl sulphinyl, amino, carbonyl, halogen, hydrogen, oxo, thio, phosphate, sulfoxide, sulfone or deuterium, and when R 5 is oxo, it may be linked to the carbon atom bearing R 3 ;
  • R 6 is loweralkyl, hydrogen, oxo, hydroxyloweralkyl, loweralkoxy, halogen, thio, sulfoxide, sulfone, phosphate or deuterium;
  • R 7 is carboxyl, hydroxy, aldehyde, hydroxyloweralkyl, alkoxyloweralkyl, loweralkoxycarbonyl, loweracyloxyloweralkyl, acetylloweralkyl, acetoxyloweralkyl, loweralkanoyl, loweralkylamino, diloweralkylamino, loweralkoxy, loweracyloxy, loweralkylthio, loweralkyl sulphonyl, loweralkyl sulphinyl, amino, carbonyl, halogen, hydrogen, oxo, thio, phosphate, sulfoxide, sulfone or deuterium, and when R 7 is oxo, it may be linked to the carbon atom bearing R 3 ; and wherein the dotted lines may each represent a single bond and the double dotted line represents either a double bond or a triple bond,
  • R 1 or R 6 is absent if the dotted line adjacent to R 1 and R 6 is a single bond
  • R 2 is absent if either of the dotted lines adjacent to R 2 is a single bond
  • the alkyl group bearing R 7 is absent if the dotted line adjacent to the alkyl group bearing R 7 is a single bond, and isomers and functional derivatives thereof,
  • R, R 1 , R 2 , R 4 , R 5 , R 6 or R 7 are phosphate, sulfoxide or sulfone.
  • compositions of the present invention can be applied in combination with other fungicides and/or other growth regulators such as auxins, ethylene, gibberellins, cytokinins and brassinolides to form agricultural solutions possessing freezing and/or chilling tolerance as well as germination enhancing properties.
  • other growth regulators such as auxins, ethylene, gibberellins, cytokinins and brassinolides
  • the agricultural compositions of the present invention are useful to increase plant resistance to water loss through stomata by stimulating the closure of plant stomata, to promote plant emergence, to act as hardeners or dehardeners and to promote freeze resistance in plants and to improve plant resistance to low temperature injury.
  • compositions of the present invention to stimulate the closure of stomata is especially beneficial when transplanting plants.
  • plants can experience tremendous shock, wilt and die. Closing the stomata of plants prior to transplanting has proved to be efficient in promoting quick recovery.
  • compositions of the present invention provide the possibility to either enhance or reduce temperature resistance of plants, to enhance plant resistance to herbicides, to overcome both low and high temperature dormancy and to improve drought and freeze resistance in plants.
  • compositions of the present invention can be synthesized in short efficient sequences from inexpensive starting materials.
  • the structures and stereochemistry of the synthesized compounds can then be easily established.
  • R is carboxyl, aldehyde, hydroxy, hydroxyloweralkyl, alkoxyloweralkyl, loweralkoxycarbonyl, loweracyloxy- loweralkyl, acetylloweralkyl, loweralkanoyl, loweralkylamino, diloweralkylamino, loweralkoxy, loweracyloxy, loweralkylthio, loweralkyl sulphonyl, loweralkyl sulphinyl, amino, carbonyl, halogen, thio, phosphate, sulfoxide, sulfone, deuterium or cycloalkyl or cycloalkoxy having from 4 to 6 carbon atoms which is optionally substituted by loweralkyl, halogen, oxygen, hydroxy or loweralkoxy;
  • R 1 is loweralkyl, hydrogen, oxo, hydroxyloweralkyl, loweralkoxy, halogen, thio, sulfoxide, sulfone, phosphate or deuterium;
  • R 2 is hydrogen, oxo, hydroxy, halogen, thio, phosphate, sulfoxide, sulfone or deuterium;
  • R 3 is oxo, thio, carboxyl, aldehyde, loweralkyl, hydroxyloweralkyl, alkoxyloweralkyl, loweralkoxycarbonyl, loweracyloxy- loweralkyl, acetylloweralkyl, loweralkanoyl, loweralkylamino, diloweralkylamino, loweralkoxy, loweracyloxy, loweralkylthio, loweralkylhalide, loweralkyldeuterium, loweralkyl sulphonyl, loweralkyl sulphinyl, or carbonyl;
  • R 2 when R 2 is oxo or thio, R 2 may be linked to both C 1 and C 2 carbon atoms to form an epoxy or a thioepoxy ring;
  • R 4 is hydrogen, oxo, halogen, thio, phosphate, sulfoxide, sulfone, deuterium, hydroxy, loweralkylsiloxane, carboxyl, aldehyde, hydroxyloweralkyl, alkoxyloweralkyl, loweralkoxycarbonyl, loweracyloxyloweralkyl, acetylloweralkyl, loweralkanoyl, loweralkylamino, diloweralkylamino, loweralkoxy, loweracyloxy, loweralkylthio, loweralkyl sulphonyl, loweralkyl sulphinyl, amino, carbonyl, cycloalkyl or cycloalkoxy having from 4 to 6 carbon atoms which is optionally substituted by loweralkyl, halogen,
  • R 4 when R 4 is oxo or thio, R 4 may be linked to the carbon atom adjacent to R 5 to form an epoxy or thioepoxy ring;
  • R 5 is carboxyl, hydroxy, aldehyde, hydroxyloweralkyl, alkoxyloweralkyl, loweralkoxycarbonyl, loweracyl- oxyloweralkyl, acetylloweralkyl, acetoxyloweralkyl, loweralkanoyl, loweralkylamino, diloweralkylamino, loweralkoxy, loweracyloxy, loweralkylthio, loweralkyl sulphonyl, loweralkyl sulphinyl, amino, carbonyl, halogen, hydrogen, oxo, thio, phosphate, sulfoxide, sulfone or deuterium, and when R 5 is oxo, it may be linked to the carbon atom bearing R 3 ;
  • R 6 is loweralkyl, hydrogen, oxo, hydroxyloweralkyl, loweralkoxy, halogen, thio, sulfoxide, sulfone, phosphate or deuterium;
  • R 7 is carboxyl, hydroxy, aldehyde, hydroxyloweralkyl, alkoxyloweralkyl, loweralkoxycarbonyl, loweracyloxy-
  • loweralkyl acetylloweralkyl, acetoxyloweralkyl, loweralkanoyl, loweralkylamino, diloweralkylamino, loweralkoxy, loweracyloxy, loweralkylthio, loweralkyl sulphonyl, loweralkyl sulphinyl, amino, carbonyl, halogen, hydrogen, oxo, thio, phosphate, sulfoxide, sulfone or deuterium, and when R 7 is oxo, it may be linked to the carbon atom bearing R 3 ; and wherein
  • the dotted lines may each represent a single bond and the double dotted line represents either a double bond or a triple bond,
  • R 1 or R 6 is absent if the dotted line adjacent to R 1 and R 6 is a single bond
  • R 2 is absent if either of the dotted lines adjacent to R 2 is a single bond
  • the alkyl group bearing R 7 is absent if the dotted line adjacent to the alkyl group bearing R 7 is a single bond, and isomers and functional derivatives thereof,
  • R 1 is CH 3
  • R 2 is oxo or OH
  • R 3 is CH 3
  • R 4 is oxo or H
  • R 5 is H
  • the present invention relates to a method for enhancing low temperature tolerance in plants which comprises treating plants with an effective amount of a solution comprising at least one compound having the following formula (I) :
  • R is carboxyl, aldehyde, hydroxy, hydroxyloweralkyl, alkoxyloweralkyl, loweralkoxycarbonyl, loweracyloxylowera lkyl , acetyl loweralkyl , loweralkanoyl , loweralkylamino , diloweralkylamino , loweralkoxy, loweracyloxy, loweralkylthio, loweralkyl sulphonyl, loweralkyl sulphinyl, amino, carbonyl, halogen, thio, phosphate, sulfoxide, sulfone, deuterium or cycloalkyl or cycloalkoxy having from 4 to 6 carbon atoms which is optionally substituted by loweralkyl, halogen, oxygen, hydroxy or loweralkoxy;
  • R 1 is loweralkyl, hydrogen, oxo, hydroxyloweralkyl, loweralkoxy, halogen, thio, sulfoxide, sulfone, phosphate or deuterium;
  • R 2 is hydrogen, oxo, hydroxy, halogen, thio, phosphate, sulfoxide, sulfone or deuterium;
  • R 3 is oxo, thio, carboxyl, aldehyde, loweralkyl, hydroxyloweralkyl, alkoxyloweralkyl, loweralkoxycarbonyl, loweracyloxy- loweralkyl, acetylloweralkyl, loweralkanoyl, loweralkylamino, diloweralkylamino, loweralkoxy, loweracyloxy, loweralkylthio, loweralkylhalide, loweralkyldeuterium, loweralkyl sulphonyl, loweralkyl sulphinyl, or carbonyl;
  • R 2 when R 2 is oxo or thio, R 2 may be linked to both C 1 and C 2 carbon atoms to form an epoxy or a thioepoxy ring;
  • R 3 when R 3 is oxo or thio, R 3 may be linked to the carbon atom adjacent to R 5 to form an epoxy or thioepoxy ring;
  • R 4 is hydrogen, oxo, halogen, thio, phosphate, sulfoxide, sulfone, deuterium, hydroxy, loweralkylsiloxane, carboxyl, aldehyde, hydroxyloweralkyl, alkoxyloweralkyl, lower- alkoxycarbonyl, loweracyloxyloweralkyl, acetylloweralkyl, loweralkanoyl, loweralkyl amino, diloweralkylamino, loweralkoxy, loweracyloxy, loweralkylthio, loweralkyl sulphonyl, loweralkyl sulphinyl, amino, carbonyl, cycloalkyl or cycloalkoxy having from 4 to 6 carbon atoms which is optionally substituted by loweralkyl,
  • R 4 when R 4 is oxo or thio, R 4 may be linked to the carbon atom adjacent to R 5 to form an epoxy or thioepoxy ring;
  • R 5 is carboxyl, hydroxy, aldehyde, hydroxyloweralkyl, alkoxyloweralkyl, loweralkoxycarbonyl, loweracyloxyloweralkyl, acetylloweralkyl, acetoxyloweralkyl, loweralkanoyl, loweralkylamino, diloweralkylamino, loweralkoxy, loweracyloxy, loweralkylthio, loweralkyl sulphonyl, loweralkyl sulphinyl, amino, carbonyl, halogen, hydrogen, oxo, thio, phosphate, sulfoxide, sulfone or deuterium, and when R 5 is oxo, it may be linked to the carbon atom bearing R 3 ;
  • R 6 is loweralkyl, hydrogen, oxo, hydroxyloweralkyl, loweralkoxy, halogen, thio, sulfoxide, sulfone, phosphate or deuterium;
  • R 7 is carboxyl, hydroxy, aldehyde, hydroxyloweralkyl, alkoxyloweralkyl, loweralkoxycarbonyl, loweracyloxyloweralkyl, acetylloweralkyl, acetoxyloweralkyl, loweralkanoyl, loweralkylamino, diloweralkylamino, loweralkoxy, loweracyloxy, loweralkylthio, loweralkyl sulphonyl, loweralkyl sulphinyl, amino, carbonyl, halogen, hydrogen, oxo, thio, phosphate, sulfoxide, sulfone or deuterium, and when R 7 is oxo, it may be linked to the carbon atom bearing R 3 ; and wherein
  • the dotted lines may each represent a single bond and the double dotted line represents either a double bond or a triple bond,
  • R 1 or R 6 is absent if the dotted line adjacent to R 1 and R 6 is a single bond
  • R 2 is absent if either of the dotted lines adjacent to R 2 is a single bond
  • the alkyl group bearing R 7 is absent if the dotted line adjacent to the alkyl group bearing R 7 is a single bond, and isomers and functional derivatives thereof,
  • an acceptable agricultural carrier comprising an agriculturally acceptable carrier cation when R, R 1 , R 2 , R 4 , R 5 , R 6 , or R 7 are phosphate, sulfoxide or sulfone, for the purpose of enhancing low temperature tolerance in plants.
  • a plant seed treated with the agricultural composition referred to above is also within the scope of the present invention.
  • Figure 1 represents the influence of compound PBI-11 on the emergence of Katepwa wheat seedlings at low temperature.
  • Figure 2 represents the influence of compound PBI-10 on the emergence of Tobin Canola seedlings
  • Figure 3 represents the influence of compound PBI-10 on the emergence of Westar Canola at low temperature.
  • Figure 4 represents the frost tolerance of winter rye treated with various compounds of the invention.
  • Figure 5 shows the regrowth of rye seedlings submitted to freezing conditions following a root drench treatment with ABA.
  • Figures 6a and 6b show the regrowth of rye seedlings submitted to freezing conditions following a root drench treatment with PBI-54.
  • Figure 7 represents the effect of chain bond order at C-4, C-5 and C-2', C-3' on freezing resistance of seedlings.
  • Figure 8 represents the effect of chain bond order at C-2', C-3' and C-1 of compounds of the invention on freezing resistance of rye seedlings.
  • Figure 9 represents the effect of chain bond order at C-4, C-5 and C-1 of compounds of the invention on freezing resistance of rye seedlings.
  • Figure 10 represents the effect of ring bond level at C-2', C-3' of compounds of the invention on freezing resistance of rye seedlings.
  • Figure 11 represents the effect of chain bond level at C-4, C-5 of compounds of the invention on freezing resistance of rye seedlings.
  • Figure 12 represents the effect of C-1 functionality of compounds of the invention on freezing resistance of rye seedlings.
  • Figure 13 represents the effect of ring bond order at C-2', C-3' , chain bond order at C-4, C-5 and functionality at C-1 of compounds of the invention on freezing resistance of rye seedlings.
  • Figure 14 represents the effect of ring bond order at C-2', C-3' and chain bond order at C-4, C-5 of compounds of the invention on freezing resistance of rye seedlings over time.
  • Figure 15 represents the effect of ring bond order at C-2', C-3' and of functionality at C-1 of compounds of the invention on freezing resistance of rye seedlings over time.
  • Figure 16 represents the effect of compounds of the invention on the induction of freezing tolerance in rye seedlings over time when applied as a foliar spray.
  • Figure 17 represents the effect of a foliar spray of seedlings of canola c.v. Touchdown with compounds of the invention on freezing resistance and low temperature growth.
  • Figure 18 represents the effect of a foliar spray of seedlings of canola c.v. Touchdown with compounds of the invention on low temperature growth.
  • halogen includes chlorine, bromine, iodine and fluorine.
  • loweralkyl, loweracyloxyloweralkyl, loweralkanoyl, loweralkoxycarbonyl, loweralkoxy and loweracyloxy wherever employed, include straight and branched alkyl, acyloxyloweralkyl, alkanoyl, alkoxy and acyloxy groups having 1 to 10 carbon atoms in the alkyl, acyloxy- loweralkyl, alkanoyl, alkoxycarbonyl, alkoxy or acyloxy moiety.
  • the invention relates to compounds which, when applied as a root drench or a foliar spray, are useful to confer low temperature tolerance to plants.
  • low temperature tolerance is intended to include temperatures associated with chilling injury (usually between 17 and 0°C), frost injury (subzero temperatures) or both.
  • a first group is useful as chilling tolerance enhancers
  • a second group is useful to confer freezing resistance to plants at subzero temperatures
  • a third group can be used either in chilling or freezing resistance applications.
  • all groups have the ability to enhance plant tolerance to low temperature injury, either at temperatures above or below freezing.
  • composition useful to provide low temperature tolerance to plants, comprises a compound having the following formula (I) :
  • R, R 1 , R 2 , R 4 , R 5 , R 6 or R 7 are phosphate, sulfoxide or sulfone.
  • R is carboxyl, aldehyde, hydroxy, hydroxyloweralkyl, alkoxyloweralkyl, loweralkoxycarbonyl, loweracyloxy- loweralkyl, acetylloweralkyl, loweralkanoyl, cycloalkyxo having from 4 to 6 carbon atoms, amino, carbonyl, halogen or thio;
  • R 1 is loweralkyl, hydrogen, oxo, hydroxyloweralkyl, loweralkoxy, halogen, thio, sulfoxide, sulfone, phosphate or deuterium;
  • R 2 is hydrogen, hydroxy, halogen or thio
  • R 3 is carboxyl, aldehyde, loweralkyl, hydroxyloweralkyl, alkoxyloweralkyl, loweralkoxycarbonyl, loweracyloxyloweralkyl, acetylloweralkyl, loweralkanoyl, loweralkylamino, diloweralkylamino, loweralkoxy, loweralkylhalide, loweracyloxy, loweralkylthio, loweralkyl sulphonyl, loweralkyl sulphinyl or carbonyl; and when R 2 is thio, R 2 may be linked to both C 1 and C 2 carbon atoms to form a thioepoxy ring;
  • R 4 is hydrogen, oxo, halogen, thio or amino
  • R 5 is hydrogen, oxo or nitrogen
  • R 6 is hydrogen
  • R 7 is hydrogen, oxo or nitrogen.
  • a more preferred group of compounds to be used in the composition of the present invention include those having the following formula IA:
  • R is hydroxy, aldehyde, carboxyl or loweralkoxyl
  • R 1 is loweralkyl
  • R 2 is hydroxy
  • R 3 is loweralkyl or loweralkylhalide
  • R 4 is oxo
  • R 5 and R 7 are hydrogen
  • the dotted line is optionally a single bond and the double dotted line is a double bond or a triple bond; and R 7 is absent when the dotted line adjacent to R 5 is a single bond.
  • composition of the present invention are the following compounds:
  • Some of the compounds used in the context of the present invention have chemical structures containing asymetric carbon atoms, and therefore can be obtained as optical isomers.
  • the present invention therefore intends to cover racemic mixtures as well as isolated optical isomers of the compounds of formulae I and IA, obtained through resolution techniques well-known to those skilled in the art. These isomers may also be obtained through appropriate chemical synthesis, some examples of which are set forth in the present application. Generally speaking, the compounds of formulae I and IA have been used as racemic mixtures unless otherwise indicated.
  • the ability of the agricultural compositions of the present invention to enhance low temperature tolerance in plants appears to be related to specific regions of the active compound they contain.
  • nature of the functional group of substituent R, the double bond configuration at C-2, C-3, the bond order at C-4, C-5 (for example either a trans double bond or a triple bond) as well as the saturation of the ring, especially the presence or absence of a double bond at C-2', C-3' can influence the low temperature tolerance activity.
  • the carbon numbering order used in the context of the present invention was taken from the usual carbon numbering of abscisic acid.
  • the nature of the other substituents on the molecule does not appear to be as critical in affecting overall low temperature tolerance activity even though some preferred substituents have been suggested above.
  • the activity associated with any one substituent can also be influenced by the presence of other substituents.
  • cis and trans compounds appear to be more active than their corresponding acetylenic analogs unless R is an ester.
  • cyclohexenones tend to demonstrate more activity than cyclohexanones regardless of the oxidation level at R.
  • other examples showed that an acetylenic side chain decreased the activity of cyclohenenones but increased the activity of cyclohexanones relative to their cis, trans counterparts.
  • the present invention also relates to novel compounds useful to confer low temperature tolerance to plants. These compounds have the following formula (I):
  • R is carboxyl, aldehyde, hydroxy, hydroxyloweralkyl, alkoxyloweralkyl, loweralkoxycarbonyl, loweracyloxyloweralkyl, acetylloweralkyl, loweralkanoyl, cycloalkoxy having from 4 to 6 carbon atoms, amino, carbonyl, halogen or thio;
  • R 1 is loweralkyl, hydrogen, oxo, hydroxyloweralkyl, loweralkoxy, halogen, thio, sulfoxide, sulfone, phosphate or deuterium;
  • R 2 is hydrogen, hydroxy, halogen or thio
  • R 3 is carboxyl, aldehyde, loweralkyl, hydroxyloweralkyl, alkoxyloweralkyl, loweralkoxycarbonyl, loweracyloxyloweralkyl, acetylloweralkyl, loweralkanoyl, loweralkylamino, diloweralkylamino, loweralkoxy, loweralkylhalide, loweracyloxy, loweralkylthio, loweralkyl sulphonyl, loweralkyl sulphinyl or carbonyl; a preferred group of the formula I compounds are those in which
  • R is carboxyl, aldehyde, hydroxy, hydroxyloweralkyl, alkoxyloweralkyl, loweralkoxycarbonyl, loweracyloxyloweralkyl, acetylloweralkyl, loweralkanoyl, cycloalkoxy having from 4 to 6 carbon atoms, amino, carbonyl, halogen or thio;
  • R 1 is loweralkyl, hydrogen, oxo, hydroxyloweralkyl, loweralkoxy, halogen, thio, sulfoxide, sulfone, phosphate or deuterium;
  • R 2 is hydrogen, hydroxy, halogen or thio
  • R 3 is carboxyl, aldehyde, loweralkyl, hydroxyloweralkyl, alkoxyloweralkyl, loweralkoxycarbonyl, loweracyloxyloweralkyl, acetylloweralkyl, loweralkanoyl, loweralkylamino, diloweralkylamino, loweralkoxy, loweralkylhalide, loweracyloxy, loweralkylthio, loweralkyl sulphonyl, loweralkyl sulphinyl or carbonyl;
  • R 2 when R 2 is thio, R 2 may be linked to both C 1 and C 2 carbon atoms to form a thioepoxy ring;
  • R 4 is hydrogen, oxo, halogen, thio or amino
  • R 5 is hydrogen, oxo or nitrogen
  • R 6 is hydrogen; R 7 is hydrogen, oxo or nitrogen.
  • novel compounds of the present invention are prepared by alkylation of an appropriate cyclohexanone derivative with an appropriate acetylide derivative. This method is well-known to those skilled in the art.
  • the compounds of the present invention can be applied to plant parts using various vehicles to insure that the chemicals are active.
  • the rate of application should be such that a sufficient amount of the composition containing the active ingredient is applied to the targeted plant part to obtain the desired plant response to low temperature exposure.
  • the excipients used in the composition of the present invention can be selected from a wide variety of agriculturally acceptable carriers.
  • a preferred carrier is water.
  • Agents having the ability to enhance chemical uptake such as surfactants in very small percentages in the range of 0.01 to 1% are preferably used in the composition of the present invention.
  • the rate of application depends on a number of factors, such as environmental conditions, type of crop and the like. It has also been found that timing and rate of application bear a relationship to one another and to the crop to which they are applied, such that the rate of application and the timing thereof bear a relationship to the yield increase. Also, it has been discovered that the activity of some of these compounds on plants is concentration dependent since the compounds seem to be interfering with the action of some of the plant's normal hormones.
  • compositions of the present invention vary from one species to another depending on the nature and concentration of the compound used and on the method of application of the compounds.
  • a given compound may possess germination enhancement properties in Canola while another compound may be active in wheat but not in Canola.
  • some of the compositions of the present invention are highly specific to certain plant species while others are highly specific to different plant species.
  • the compounds of the present invention once dissolved in the desired carrier, are preferably applied either as a root drench or as a foliar spray. As mentioned previously, the method of application can sometimes affect efficacy of the treatment.
  • the compounds be applied as a root drench rather than a foliar spray for optimal efficacy, although both methods can be used efficiently.
  • the composition can usually be applied at a rate of from about 0.000005 g to 1.5 kg per acre, in a total applied volume of from about 5 1 to 100 1 per acre.
  • Preferred concentrations of the active compound in the foliar composition usually range between 10 -2 ⁇ M and 10 -5 ⁇ M.
  • compositions are applied by means of a root drench, the concentrations of the active compounds are the same as in the case of a foliar spray. The only difference is the fact that the compositions are applied to the roots rather than the leaves. Even though root drench application appears to be more effective at least in some plant species, foliar sprays are sufficiently effective to be used in widespread commercial applications.
  • An indication of enhanced freezing resistance in plants through application of the composition of the present invention is the fact that the dry matter content of plant cells is increased during incubation at low temperatures. Increases of the plant's dry matter content is usually accompanied by decreases in the plant's water content. Decreases in water content usually signifies an increase in freezing resistance.
  • compositions of the present invention also possess the ability to enhance germination and emergence at low temperatures. Cool soils in the spring delay germination increase the risk of fungal infection and produce uneven stands.
  • the composition described above allows better plants yields at low germination temperatures. Any seed or plant treatment which enhances germination is of considerable importance for the establishment of grasses which are slow to germinate and only a certain percentage of the seedlings survive to produce a proper coverage.
  • compositions of the present invention also promote plant growth and development at suboptimal temperatures. This is especially important in countries such as Canada where springs are cool for prolonged periods of time. Promotion of growth and development in the spring results in earlier maturity and avoids the risks of early fall frost. Since the plants can grow and develop early in the spring, they avoid midsummer periods of heat and drought. This leads to an increase in both yield and crop quality.
  • compositions of the present invention when applied to plant roots, lead to a reduction of the plant's transpiration rate.
  • Water is pulled into the plant via its roots, when a plant transpires water from its leaves. If a plant is transpiring more water than can be pulled into the plant, an automatic mechanism in the plant closes the stomata before irreversible damage occurs. When water becomes available, the stomata open.
  • the transpiration rate of a plant is proportional to the degree at which the plant's stomata are opened. A low transpiration rate therefore indicates that the plant's stomata are practically closed. This property is useful to avoid shock when transplanting from one container to another or from a container to the field.
  • the compounds of the present invention are useful as seed treatment for agronomic, forestry and horticultural crops. As well, these compounds are useful in the malting and distilling industry, where high alpha- amylase activity in germinating barley is required.
  • Ketal 1.31 g, 5.5 mmol was reacted with Z-3-methylpent-2-en-4-yn-1-ol (0.65 g, 6.7 mmol) and n-butyllithium (1.6 M in hexane, 8 mL, 12.8 mmol) in dry THF by the procedure described for the preparation of Z-5-(5-hydroxy-3-methyl-pent-3-en-1-ynyl)-3,5,5- trimethyl-2-cyclohexen-1-one.
  • molybdenum hexacarbonyl could be used in the above procedure instead of vanadyl acetylacetonate but longer reaction time was required.
  • the ketodiol 17 (30 mg, 0.11 mmol) was oxidized with manganese oxide (420 mg, 4.8 mmol) to give the corresponding aldehyde by the procedure described in Example 17.
  • the crude aldehyde was usually oxidized to ester as described in Example 23 without purification.
  • the ketosilyl ether from Example 26 (5.7 g, 21 mmol) was treated with Z-3-methylpent-2-en-4-yn-1-ol (3.0 g, 32 mmol) and n-butyllithium (1.6 M in hexane, 40 mL, 63 mmol).
  • the keto-acetate (0.94 g, 3.2 mmol) was hydrolysed by stirring with 5M NaOH (1 mL) and methanol (25 mL) at room temperature for 1 h. After working up and purification, the desired product (+)-4(Z)-(4R,5S)-4- hydroxy-4-(5-hydroxy-3-methylpent-3-en-1-ynyl)-3,3,5- trimethylcyclohexanone was obtained as colorless crystals (0.80 g, 100%), mp 96.5-98.0°C; [a]D +22.3°C (c 0.53, CH3OH); ir, 1H and 13C nmr identical with those of the (-)-(4S, 5R) enantiomer .
  • (+)-4(Z)-(4R,5S)-4-Hydroxy-4-(5-hydroxy-3- methylpent-3-en-1-ynyl)-3,3,5-trimethylcyclohexanone was treated with 2,2-dimethylpropane-1,3-diol in benzene with a catalytic amount of p-toluenesulfonic acid to afford the ketal, [a]D +27.1°C (c 0.90, CH3OH).
  • the aldehyde was prepared by the oxidation of
  • (+)-(4S, 5S)-methyl dihydroabscisate was hydrolyzed with 2M KOH and methanol to give (+)-(4S, 5S)-dihydroabscisic acid as colorless crystals, 173-180°C; [a]D +63.5°C (c 1.17, CH3OH).
  • the product 36 was obtained pure by chromatography over silica (Chromatotron, elution with 50% ether 50% hexane, as an oil that gave: ir (CHCl3) 3600 (weak), 1710 (strong) cm-1; 1H nmr -
  • Example 40 Example 40
  • the ester 36 was saponified as for compound 30 to afford the enynoic acid 37 in 83% yield.
  • (+)-(1'R, 2'R)-5',6'-Dihydroabscisic alcohol PBI-91) .
  • IR n max cm -1 (neat): 3400 (OH), 1700 (C O).
  • Compound PBI-171 was characterized as the methyl ester PB-170, m.p. 138-148°C, which had the following spectral properties: IR n max cm -1 : 3600, 3450, 1700; EIMS: m/z 278 [M-18] + (7), 248 (5), 219 (14), 191 (100); CIMS (ammonia): m/z 314 [M+18] + (100), 297 [M+1] + (4), 296 [M] + (8), 279 [M-18+1] + (30); CIMS (isobutane) : m/z 297 [M+1] + (6), 279 [M-18+1] + (62), 249 (100); trimethylsilyl ether derivative CIMS (ammonia) : m/z 386 [M+18] + (27), 369 [M+1] + (9), 368 [M] + (12), 351 [M-18+1] + (45). Anal, found:
  • (-)-Methyl 7',7'-difluoroabscisate showed the following properties:
  • Example 48
  • the seeds were dried at 35°C to a moisture content of approximately 12 percent.
  • the seeds were then planted in a soil mixture of 1 part soil, 1 part peat and 1 part vermiculite at a uniform depth of 3 cm.
  • the seeds in the soil were then transferred to a ConViron Model E-15 controlled environment chamber maintained at 10°C, in the dark. The number of seeds which emerged was determined twice a day.
  • compositions containing compound PBI-10 on the emergence of Canola at 10°C.
  • 'Tobin' 7.4 g of 'Westar' canola were soaked for 8 hours at 25°C, in each of the following solutions: water; and one of 10, 1, or 0.1 ⁇ M PBI-10 in glass beakers. Beakers were sealed with aluminum foil to prevent evaporation and to exclude light. After incubation, solutions were removed and seeds were blotted dry with paper towels. Seeds were sandwiched between 4 layers of paper towels, which were daily changed and seeds were separated, and dried at 25°C, until their dried weight was close to their pre-soaking weight.
  • Compounds in Group 1 were ABA, PBI-01, PBI-04, PBI-05, PBI-06, PBI-07, PBI-10, PBI-11, PBI-14 and PBI-15; compounds in Group 2 were ABA, PBI-16, PBI-17, PBI-18, PBI-19, PBI-34, PBI-43, PBI-37, and PBI-47.
  • Compounds at the highest concentration 1000 or 100 ⁇ M
  • a control of Ericksson's media (Group 1) or Ericksson's media with and without 1% DMSO (Group 2) was used.
  • Bromegrass cells (1 gram), aseptically added to each concentration and control (s), were incubated for 1 week at 25°C in darkness on a rotary shaker at 150 rpm. Each treatment was repeated twice for Group 1 and 3 times for Group 2. After incubation, cells were removed and weighed to determine the growth of cells in each concentration. Cells were sampled for gm water / gm dry weight and for a Freeze Test to determine the lethal temperature for 50% (LT 50 ) of the cells.
  • TTC 2,3,5-triphenyltetrazolium chloride
  • the LT 50 is that part of the curve where the absorbance value of the frozen treatment in less than one half the value of the unfrozen control.
  • Group 2 the categories were as follows: 1) the hardeners were 0.01 to 10 ⁇ M PBI-34 and all of PBI-43; 2) PBI-16 gave no response; and 3) the dehardeners were PBI-17, PBI-18, PBI-19, PBI-37, and PBI-47 (Table 2).
  • the compounds induced categories of response. These categories were, as follows: 1) hardeners (lower LT 50 than the control); 2) same as the control; and 3) dehardeners (higher LT 50 than control). Tables 1 and 2 also show that each response was dependent on the concentration.
  • the plants were tested for frost tolerance using a controlled freeze test as follows. The plants were held at -2°C for two hours to equilibrate and then the leaves of the plants were nucleated with small ice crystals to initiate freezing of water in the plant.
  • the plants were cooled to -3°C and allowed to equilibrate at that temperature for 1 hour. Plants were then removed from this temperature and allowed to thaw slowly at 4°C. The remaining plants were then cooled to -4, -5, -6, -7 and -9°C using the same protocol as described above. The frosted plants were compared to an unfrozen control after two weeks of regrowth in a glass house maintained at 25°C. The results of the freeze test are summarized in Table 3.
  • Seedlings of Brassica napus c.v. Delta (a spring type brassica) were treated with compounds PBI-01, PBI-16, PBI-37, PBI-38, PBI-40, PBI-252, PBI-260 and ABA as described in Example 54.
  • the plants were grown similar to the plants grown in Example 54 and subjected to a frost test as described in Example 54.
  • the plants were subjected to frosts two, three and four days following treatment with ABA and the compounds referred to above. The results of this test are described in Table 4.
  • Results are based on the activity of 16 compounds which were applied to the roots of tender rye seedlings. Compounds were applied as a 10-4 M root drench on two consecutive days. LT 50 values were calculated from freeze tests performed 3, 4 and 6 days after the first application.
  • Figure 7 represents the interaction between chain bond order at C-4, C-5 and ring bond order at C-2', C-3' based on the induction of freezing tolerance in rye seedlings after compounds were applied as a root drench. Values are the average of 3 freeze tests performed 3, 4 and 6 days after treatment. It can be seen from this figure that altering the ring bond order did not increase nor decrease the effect of chain bond order on compound activity, or vice versa. Compounds with ring double bonds were more effective than ones with ring single bonds, and compounds with chain triple bonds were more effective than ones with a trans double bond.
  • Figure 8 represents the interaction between ring bond order at C-2', C-3' and C-1 functionality based on the induction of freezing tolerance in rye seedlings after compounds were applied as a root drench. Values are the average of 3 freeze tests performed 3, 4 and 6 days after treatment.
  • the highly significant ring bond order by functionally at C-1 interaction stemmed primarily from esters for which activity was the same regardless of ring bond order.
  • C-1 was an acid, aldehyde or alcohol
  • the effect of ring bond order was additive with double bonds imparting greater activity than single bonds.
  • ring bond order at C-2', C-3' altered the effectiveness of the compounds over time.
  • Compounds with a C-2', C-3' double bond were more active initially than ones with a C-2', C-3' single bond.
  • the activity of compounds with a C-2', C-3' single bond however, increased over time and was equal to compounds with a C-2', C-3' double bond by day 6. Determinations were carried out with preplanned contrasts between bond level for day 3 and day 6.
  • esterification decreased the activity of cyclohexenones. but did not affect the activity of cyclohexanones.
  • the reason for this interaction is not clear, but may be related to esterase activity and rates of hydrolysis if a free carboxyl group was required for activity.
  • the C-1 has to be at the acid oxidation level to induce freezing tolerance in a bromegrass cell suspension culture.
  • the greater activity of analogs with a triple bond at C-4, C-5 may also partially relate to the rate of hydrolysis as acetylenic esters were of equal activity to acetylenic acids, but dienoic esters were less active than dienoic acids.
  • Seedlings of a Graminae species winter rye (Secale cereale) cv Puma were grown at 25°C in a glass house. At the two to three leaf stage, seedlings grown in vermiculite received a foliar application of 100 ⁇ M ABA analogs. A mesting bottle was used for foliar applications and approximately 0.5 ml of solution per plant was applied. Sixteen compounds were tested for increasing the freezing tolerance of the rye. The plants were tested for freezing tolerance as described in Example 54. Following the controlled freeze test the plants were evaluated for frost tolerance after three weeks growth in a glasshouse at 25°C. Results are summarized in Figure 16. When compared to the results from a root application of the same analogs, lesser compounds showed a consistent response to time when applied as a foliar spray. However, compounds such as PBI-54 and PBI-11 maintained more consistent activities over time.
  • Foliar applied ABA may be rapidly ion trapped in the phloem which has a pH of 7.5.
  • Studies with radiolabelled ABA have shown that foliar applied ABA is translocated very slowly to strong sinks such as young leaves.
  • root applied ABA rapidly accumulates in the xylem stream.
  • the xylem sap is typically pH 5.5 to 6.5, therefore, ABA is not ion trapped and has access to all tissues that are continuous with the apoplast.
  • the crown is the critical region for survival in cereals, therefore, ABA must come into contact with this tissue if there is to be a response.
  • the crown contains the meristems in cereal seedlings, which are strong sinks for photosynthate. Xylem vessels also pass through the crown, therefore, both methods of application would expose the crown to ABA.
  • the marked differences in response to the method of application must be due to either lesser foliar uptake or the location of the ABA receptor (s) governing acclimation.
  • the location of the ABA receptor (s) for cold hardening is unknown, the situation may be analogous to that of stomata.
  • Stomatal receptors are on the plasma membrane and are sensitive to the apoplastic concentration of ABA.
  • Phaseolus vulgaris (beans) grown at 25°C in a peat mixture were soil drenched with approximately 50 mls of either water, ABA and the compounds PBI-03, PBI-19, PBI-16 and PBI-11 (all chemicals at 10 -6 M). The plants were held at 25°C with a 16 hour photoperiod. After seven days the plants were transferred to 25°C and allowed to grow for an additional 14 days. The plants were evaluated for injury (visually) based on a scale of 0 to 5 when 0 indicates no injury and 5 indicates complete necrosis.
  • Seeds of tomato (Lycopersicon esculentum cv. Swift) were sown to a 1:2 mix of peat moss and vermiculite in a glass house maintained at 25°C. At the two leaf stage the seedlings were transplanted a "Styrofoam tray" containing holes of 3 cm in diameter by 12 cm deep. The roots of the seedlings were covered with greenhouse grade vermiculite. Plants were grown in the glass house at a light intensity of 350 ⁇ mol/sec/m 2 and fertilized every third day with a 10% solution of a 20-20-20 (N-P-K) fertilizer. When the plants were 20 to 30 cm in height
  • ABA analogs PBI-01, PBI-37, PBI-40 and PBI-53 at either 1 or 10 ⁇ M. Racemic ABA at equivalent concentrations was also added to the tomato plants as a comparison treatment.
  • Plants treated with PBI-16 and PBI-37 had the lowest value transpiration rates. Plants treated with PBI-40, PBI-16 and PBI-37 flowered 4 days earlier than the control. According to statistical analysis these results are significant (Table 3). Plants treated with PBI-40 and racemic ABA suffered the lowest losses due to transplant shock in the field.
  • Tomato plants cv. Swift were grown as described previously in Example 59. The plants were treated with the following compounds: -ABA, PBI-37, PBI-40, PBI-11, PBI-63 and PBI-51.
  • the tomato plants were chilled for 0, 2, 4 and 6 days in one trial and for 0, 2, 4, 7 and 9 days in a second trial. For both cases, the chilling temperatures was 5°C.
  • the results of the treatments on chilling injury to tomatoes is shown in Tables 4 and 5.
  • the effect of the treatments on chilling injury to tomatoes is shown in Tables 4 and 5.
  • the effect of the treatments is shown in Table 8.
  • Tomato plants exposed to chilling temperatures were protected for 2 days. The trend was to afford protection for also 4 days of chilling temperatures. Plants treated with -ABA also flowered 6 to 13 days earlier than the controls. The compound PBI-37 flowered 3 to 10 days earlier than the controls.

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Abstract

Composition servant à conférer aux plantes agricoles une tolérance aux basses températures. Elle comporte une quantité efficace d'un composé répondant à la formule (I). La composition comprend des composés dont certains sont de nouveaux dérivés d'acide abscisique. On a également prévu des procédés de traitement de plantes et de tissus végétaux tels que les graines à l'aide de compositions du type précité.
PCT/CA1994/000005 1993-01-07 1994-01-07 Utilisation de composes pour conferer aux plantes une tolerance aux basses temperatures Ceased WO1994015467A1 (fr)

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0887017A4 (fr) * 1996-02-08 2002-06-12 Sagami Chem Res Accelerateur de croissance pour plantes
US8283481B2 (en) 2008-12-23 2012-10-09 National Research Council Of Canada Inhibitors of a 9-cis epoxycarotenoid dioxygenase
WO2012139890A1 (fr) 2011-04-15 2012-10-18 Bayer Cropscience Ag 5-(cyclohex-2-én-1-yl)-penta-2,4-diènes et 5-(cyclohex-2-én-1-yl)-pent-2-èn-4-ines substitués en tant que principes actifs contre le stress abiotique des végétaux
WO2012139891A1 (fr) 2011-04-15 2012-10-18 Bayer Cropscience Ag Vinyl- et alcinyl-cyclohexénols substitués en tant que principes actifs contre le stress abiotique des végétaux
WO2012139892A1 (fr) 2011-04-15 2012-10-18 Bayer Cropscience Ag 5-(bicyclo[4.1.0]hept-3-én-2-yl)-penta-2,4-diènes et 5-(bicyclo[4.1.0]hept-3-én-2-yl)-pent-2-èn-4-ines substitués en tant que principes actifs contre le stress abiotique des végétaux
EP2740720A1 (fr) * 2012-12-05 2014-06-11 Bayer CropScience AG Dérivés d'acides pent-2-en-4-ines bicycliques et tricycliques substitués et leur utilisation pour augmenter la tolérance au stress chez les plantes
EP2740356A1 (fr) * 2012-12-05 2014-06-11 Bayer CropScience AG Dérivés d'acides (2Z)-5(1-hydroxycyclohexyl)pent-2-en-4-ines substitués
WO2014086751A1 (fr) * 2012-12-05 2014-06-12 Bayer Cropscience Ag Utilisation de 1-(aryléthinyl)-cyclohexanols, 1-(hétéroaryléthinyl)-cyclohexanols, 1-(hétérocyclyléthinyl)-cyclohexanols et 1-(cyloalcényléthinyl)-cyclohexanols substitués comme principes actifs contre le stress abiotique des plantes
WO2016012362A1 (fr) 2014-07-22 2016-01-28 Bayer Cropscience Aktiengesellschaft Cyano-cycloalkylpenta-2,4-diènes, cyano-cycloalkylpent-2-èn-4-ynes, cyano-hétérocyclylpenta-2,4-diènes et cyano-hétérocyclylpent-2èn-4-ynes substitués utilisés comme principes actifs contre le stress abiotique des plantes
WO2016047532A1 (fr) * 2014-09-24 2016-03-31 国立大学法人静岡大学 Dérivé d'acide abscissique
WO2016187368A1 (fr) * 2015-05-19 2016-11-24 Valent Biosciences Corporation Dérivés d'acide (s)-abscissique pour une meilleure coloration du raisin
WO2016187369A1 (fr) * 2015-05-19 2016-11-24 Valent Biosciences Corporation Dérivés d'acide (s)-abscissique pour l'éclaircissage
WO2016187370A1 (fr) * 2015-05-19 2016-11-24 Valent Biosciences Corporation Dérivés d'acide (s)-abscissique pour améliorer la tolérance au stress des plantes

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EP0887017A4 (fr) * 1996-02-08 2002-06-12 Sagami Chem Res Accelerateur de croissance pour plantes
US8283481B2 (en) 2008-12-23 2012-10-09 National Research Council Of Canada Inhibitors of a 9-cis epoxycarotenoid dioxygenase
US9185914B2 (en) 2011-04-15 2015-11-17 Bayer Intellectual Property Gmbh Substituted 5-(cyclohex-2-en-1-yl)-penta-2,4-dienes and 5-(cyclohex-2-en-1-yl)-pent-2-en-4-ines as active agents against abiotic stress in plants
AU2012242124B2 (en) * 2011-04-15 2017-05-25 Bayer Intellectual Property Gmbh Substituted 5-(cyclohex-2-en-1-yl)-penta-2,4-dienes and 5-(cyclohex-2-en-1-yl)-pent-2-en-4-ynes as active agents against abiotic stress in plants
WO2012139892A1 (fr) 2011-04-15 2012-10-18 Bayer Cropscience Ag 5-(bicyclo[4.1.0]hept-3-én-2-yl)-penta-2,4-diènes et 5-(bicyclo[4.1.0]hept-3-én-2-yl)-pent-2-èn-4-ines substitués en tant que principes actifs contre le stress abiotique des végétaux
CN103596923A (zh) * 2011-04-15 2014-02-19 拜耳知识产权有限责任公司 作为在植物中抵抗非生物胁迫的活性剂的取代的5-(环己-2-烯-1-基)-戊-2,4-二烯和5-(环己-2-烯-1-基)-戊-2-烯-4-炔
US20140051577A1 (en) * 2011-04-15 2014-02-20 Jens Frackenpohl Substituted 5-(bicyclo[4.1.0]hept-3-en-2-yl)penta-2,4-dienes and 5-(bicyclo[4.1.0]hept-3-en-2-yl)pent-2-ene-4-ines as active agents against abiotic stresses in plants
US20140080704A1 (en) * 2011-04-15 2014-03-20 Jens Frackenpohl Substituted vinyl and alkinyl cyclohexenols as active agents against abiotic stress in plants
JP2014511868A (ja) * 2011-04-15 2014-05-19 バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー 植物における非生物的ストレスに対する活性薬剤としての置換５−（シクロヘキス−２−エン−１−イル）−ペンタ−２，４−ジエン類および５−（シクロヘキス−２−エン−１−イル）−ペント−２−エン−４−イン類
WO2012139890A1 (fr) 2011-04-15 2012-10-18 Bayer Cropscience Ag 5-(cyclohex-2-én-1-yl)-penta-2,4-diènes et 5-(cyclohex-2-én-1-yl)-pent-2-èn-4-ines substitués en tant que principes actifs contre le stress abiotique des végétaux
WO2012139891A1 (fr) 2011-04-15 2012-10-18 Bayer Cropscience Ag Vinyl- et alcinyl-cyclohexénols substitués en tant que principes actifs contre le stress abiotique des végétaux
EP2740356A1 (fr) * 2012-12-05 2014-06-11 Bayer CropScience AG Dérivés d'acides (2Z)-5(1-hydroxycyclohexyl)pent-2-en-4-ines substitués
EP2740720A1 (fr) * 2012-12-05 2014-06-11 Bayer CropScience AG Dérivés d'acides pent-2-en-4-ines bicycliques et tricycliques substitués et leur utilisation pour augmenter la tolérance au stress chez les plantes
WO2014086751A1 (fr) * 2012-12-05 2014-06-12 Bayer Cropscience Ag Utilisation de 1-(aryléthinyl)-cyclohexanols, 1-(hétéroaryléthinyl)-cyclohexanols, 1-(hétérocyclyléthinyl)-cyclohexanols et 1-(cyloalcényléthinyl)-cyclohexanols substitués comme principes actifs contre le stress abiotique des plantes
WO2016012362A1 (fr) 2014-07-22 2016-01-28 Bayer Cropscience Aktiengesellschaft Cyano-cycloalkylpenta-2,4-diènes, cyano-cycloalkylpent-2-èn-4-ynes, cyano-hétérocyclylpenta-2,4-diènes et cyano-hétérocyclylpent-2èn-4-ynes substitués utilisés comme principes actifs contre le stress abiotique des plantes
US10322995B2 (en) 2014-07-22 2019-06-18 Bayer Cropscience Aktiengesellschaft Substituted cyano cycloalkyl penta-2,4-dienes, cyano cycloalkyl pent-2-en-4-ynes, cyano heterocyclyl penta-2,4-dienes and cyano heterocyclyl pent-2-en-4-ynes as active substances against abiotic plant stress
JPWO2016047532A1 (ja) * 2014-09-24 2017-07-13 国立大学法人静岡大学 アブシジン酸誘導体
WO2016047532A1 (fr) * 2014-09-24 2016-03-31 国立大学法人静岡大学 Dérivé d'acide abscissique
US10125095B2 (en) 2014-09-24 2018-11-13 National University Corporation Shizuoka University Abscisic acid derivative
US9872492B2 (en) 2015-05-19 2018-01-23 Valent Biosciences Llc (S)-abscisic acid derivatives for thinning
WO2016187370A1 (fr) * 2015-05-19 2016-11-24 Valent Biosciences Corporation Dérivés d'acide (s)-abscissique pour améliorer la tolérance au stress des plantes
US9877480B2 (en) 2015-05-19 2018-01-30 Valent Biosciences Llc (S)-abscisic acid derivatives for enhanced grape coloration
WO2016187369A1 (fr) * 2015-05-19 2016-11-24 Valent Biosciences Corporation Dérivés d'acide (s)-abscissique pour l'éclaircissage
US10314307B2 (en) 2015-05-19 2019-06-11 Valent Biosciences Llc (S)-abscisic acid derivatives for improving plant stress tolerance
WO2016187368A1 (fr) * 2015-05-19 2016-11-24 Valent Biosciences Corporation Dérivés d'acide (s)-abscissique pour une meilleure coloration du raisin

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