WO2002051811A1 - Derivatives of acetic acid for increasing abiotic stress tolerance of cultivated plants - Google Patents

Derivatives of acetic acid for increasing abiotic stress tolerance of cultivated plants Download PDF

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Publication number
WO2002051811A1
WO2002051811A1 PCT/HU2001/000152 HU0100152W WO02051811A1 WO 2002051811 A1 WO2002051811 A1 WO 2002051811A1 HU 0100152 W HU0100152 W HU 0100152W WO 02051811 A1 WO02051811 A1 WO 02051811A1
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group
nitrogen
amino group
lower alkyl
general formula
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PCT/HU2001/000152
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English (en)
French (fr)
Inventor
Jeno Szilbereky
Gáborné BARLA SZABÓ
Gábor GALIBA
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Sinnex Muszaki Fejleszto És Tanácsadó Kft.
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Publication of WO2002051811A1 publication Critical patent/WO2002051811A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals

Definitions

  • the present invention relates to new acetic acid derivatives of the following general formula:
  • R 1 is a phenyl group or a five- or six-membered unsaturated heterocyclic ring containing nitrogen as heteroatom;
  • R 2 is a hydrogen atom or a lower alkyl group
  • X is an amino group optionally substituted with one or two lower alkyl groups; or a halogen atom, preferably chlorine or bromine;
  • Y is a hydroxyl group, a lower alkoxy group, an amino group optionally substituted with a five- or six-membered saturated heterocyclic ring containing two identical or different heteroatoms selected from nitrogen and oxygen atoms or with a lower carboxyalkyl group, or an amino group the substituents of which are replacing both of its hydrogen atoms and are forming with the enclosed nitrogen atom a five- or six-membered heterocyclic group containing two nitrogen atoms, where the other nitrogen atom is optionally substituted by a lower alkyl group; with the proviso that if R 2 is a hydrogen atom or a lower alkyl group, X is a halogen atom and Y is a lower alkoxy group, then R 1 can only be a five- or six-membered unsaturated heterocyclic ring containing nitrogen as a heteroatom.
  • R 1 is a phenyl group or a five- or six-membered unsaturated heterocyclic ring containing nitrogen as heteroatom;
  • R is a hydrogen atom or a lower alkyl group;
  • X is an amino group optionally substituted with one or two lower alkyl groups; or a halogen atom, preferably chlorine or bromine;
  • Y is a hydroxyl group, a lower alkoxy group, an amino group optionally substituted with a five- or six-membered saturated heterocyclic ring containing two identical or different heteroatoms selected from nitrogen and oxygen atoms or with a lower carboxyalkyl group, or an amino group the substituents of which are replacing both of its hydrogen atoms and are forming with the enclosed nitrogen atom a five- or six-membered heterocyclic group containing two nitrogen atoms, where the other nitrogen atom is optionally substituted by a lower alkyl group; and to that of the agriculturally acceptable salts of the above compounds, as well as compositions containing such compounds or their agriculturally acceptable salts, and methods for increasing abiotic stress tolerance of cultivated plants, and for inhibiting the senescence of seeds and enhancing their vigour under stress conditions.
  • Hungarian Patent Application No. P9700792 discloses in details the effects of the different extremities of the weather on the development of plants.
  • the same patent application describes the use of hydroxylamine derivatives. According to the description, these compounds bring the protective system of the plants into action as a response to extreme weather conditions, and as a result of the induced metabolic processes the cold, frost and drought tolerances of the plants improve.
  • the drawback of this procedure which hampers the protection of plants against the extremities of the weather is that plants respond differently to the extremities of the weather and the circumstances of the occurrence of said extremities (e.g. time, extent) are unpredictable.
  • the disadvantage of the hormones is that they affect the hormone system of the plants and modify, for instance, the hormonal equilibrium and the metabolic processes in the plants, therefore, they may result in unpredictable physiological changes. Thus, these compounds can only be applied in limited areas, with special care, after running greater number of special preliminary experiments than usual.
  • tefrahydrofurfuryl alcohol tetrahydrofurfuryl a ine or a combination thereof is used to increase the cold resistance of plants.
  • Hungarian Patent No. 181241 secunder or tertier beta-hydroxyethylamines, or the corresponding quaternary ammonium salts are recommended to enhance the tolerance of plants against cold and frost.
  • the compounds used in these methods need to be applied several times, also when the cold is over, preferably regularly, all-around the surface of the plant, therefore, these solutions are disadvantageous from application technique aspects.
  • the main disadvantage of these applications is that they are particularly labour- intensive.
  • Stimulating the growth of cultivated plants is possible as early as the sowing time and several methods are known in the art.
  • adenine derivatives are applied that increase the activity of plant cytokines thereby stimulating the germinating ability of the plants and the development of new shoots, moreover increase the yield of crop.
  • oxadiazol derivatives are used to stimulate plant growth.
  • seeds are coated with clavibacter microorganisms that effect the germination of the seeds advantageously.
  • R 1 is a phenyl group or a five- or six-membered unsaturated heterocyclic ring
  • R 2 is a hydrogen atom or a lower alkyl group
  • X is an amino group optionally substituted with one or two lower alkyl groups; or a halogen atom, preferably chlorine or bromine;
  • Y is a hydroxyl group, a lower alkoxy group, an amino group optionally substituted with a five- or six-membered saturated heterocyclic ring containing two identical or different heteroatoms selected from nitrogen and oxygen atoms or with a lower carboxyalkyl group, or an amino group the substituents of which are replacing both of its hydrogen atoms and are forming with the enclosed nitrogen atom a five- or six-membered heterocyclic group containing two nitrogen atoms, where the other nitrogen atom is optionally substituted by a lower alkyl group; are more beneficial to enhance cold, frost and drought tolerance of plants than the compounds used earlier.
  • R 1 is a phenyl or pyridil group
  • R 2 is a hydrogen atom or a lower alkyl group
  • X is an amino group or a halogen atom
  • Y is a hydroxyl, lower alkoxy or substituted amino group are preferred.
  • Especially beneficial compounds are those in which
  • R 1 is a pyridil group
  • R 2 is a hydrogen atom
  • X is an amino group or a chlorine atom
  • Y is a hydroxyl or substituted amino group.
  • the most beneficial compound according to the invention is [(pyridin-3- carboximidoyl)aminooxy] acetic acid.
  • Agriculturally acceptable salts of the compounds according to the invention formed with organic or inorganic acids are, for example, hydrochlorides, sulphates, nitrates, phosphates, acetates.
  • R 1 is a phenyl group or a five- or six-membered unsaturated heterocyclic ring containing nitrogen as heteroatom;
  • R l is a hydrogen atom or a lower alkyl group
  • X is an amino group optionally substituted with one or two lower alkyl groups; or a halogen atom, preferably chlorine or bromine;
  • Y is a hydroxyl group, a lower alkoxy group, an amino group optionally substituted with a five- or six-membered saturated heterocyclic ring containing two identical or different heteroatoms selected from nitrogen and oxygen atoms or with a lower carboxyalkyl group, or an amino group the substituents of which are replacing both of its hydrogen atoms and are forming with the enclosed nitrogen atom a five- or six-membered heterocyclic group containing two nitrogen atoms, where the other nitrogen atom is optionally substituted by a lower alkyl group; with the proviso that if R 2 is a hydrogen atom or a lower alkyl group, X is a halogen atom and Y is a lower alkoxy group, then R 1 can only be a five- or six-membered unsaturated heterocyclic ring containing nitrogen as a heteroatom; are new.
  • Fig. 1 is the representation of the root and shoot length of cold tolerant Dunghan Shaly (DuSh) and cold sensitive Javae and CAN8603 rice types at 18 °C after 21 days of germination.
  • Treatments blank column - control; bright column - 1 mg SIN- 5/100 seeds; dark column - 15 mg SIN-5/100 seeds. Results marked by *, ** and *** are significantly differ from control sample if *, p ⁇ 0.05, **, p ⁇ 0.01 and *** , pO.OOl, respectively.
  • Fig. 2 is the representation of the number of baby fruits after drought test.
  • plants were sprayed with different concentrations of aqueous solutions of SIN-5: control (DO) sprayed with water; Dl: 5 mg/1; D2: 10 mg/1; D3: 25 mg/1.
  • Result marked by * significantly differs from the control if p ⁇ 0.05.
  • Fig. 3 is the representation of the number of pods on soybean plants following the drought period. Before the water deprivation period plants were sprayed with different concentration aqueous solutions of compound SIN-5: control (DO): sprayed with water; Dl: 10 mg/1; D2: 25 mg/1; D3: 50 mg/1. Result marked by * significantly differs from the control ifp ⁇ 0.05.
  • Fig. 4 is the representation of the effect of coating corn caryopses with SIN-5 on fresh weight of corn plantlets after cultivation in gradient chamber for 37 days.
  • R 1 , X and Y are as defined for general formula (I) - or an acid-additional salt thereof is treated with a diazoting agent known er se (see Werner, Chemische Berichte 26, p. 1567, and Werner, Chemische Berichte 28, p. 1374).
  • alkali metal nitrites potassium or sodium nitrite
  • alkyl nitrites e.g. isoamyl nitrite
  • a hydrogen halide hydroochloric acid, hydrogen bromide, etc.
  • the reaction is carried out at the boiling point of the solvent in the presence of potassium tert-butylate or potassium hydroxide (Organic Reactions, 1953, Vol. 7, pages 343 and 373, Journal fur Praktician Chemie 66, p 353., Liebigs Ann. 250, p. 165).
  • a compound wherein Y is an optionally substituted amino group is to be produced, the corresponding amine of the formula Y-H is reacted with a compound of the general formula
  • the compounds according to the invention of the general formula (I) are equally suitable for the treatment of the seed, the seedling and the fully developed plant.
  • the compounds are applied to the plants or to the seeds by the general methods of plant protection.
  • the plant or its seed is treated with an acetic acid derivative of the general formula (I), wherein the substituents are as defined above, or with an agriculturally acceptable salt thereof.
  • the compound is applied in aqueous solution or as a preparation that contains usual auxiliary materials, in addition to the active ingredient, e.g. those aiding the coating, spraying, distribution and absorption of the active agent.
  • the dose and application concentration of the active ingredients of general formula (I) depend on the species or type of the plant to be protected and on the method of use.
  • the seeds of the plants are treated with the compounds of the general formula (I).
  • the seed is coated with a preparation suitable for coating, containing the active ingredient, it is preferably pearled, optionally pelleted or simply treated with the aqueous solution of the active ingredient, for example soaked in the aqueous solution of a compound of the general formula (I) or its salt.
  • the coating of the seeds is preferably achieved by pelleting with pelleting agents that contain a compound of the general formula (I) or its salt in 0.01-1 g/litre concentration and the usual ingredients and auxiliary materials.
  • the pelleting agents may contain additional active ingredients beside the compounds of the general formula (I), for example fungicides, additives promoting germination and microelements.
  • the pelleting agent is applied in small volume, for instance, when treating rice, capsicum, soya-bean or corn seed, 1 ml pearling agent is used per 100 seeds which is dried onto the seeds uniformly during constant stirring.
  • the plant is sprayed with a dispersion medium containing a compound of the general formula (I) or a salt thereof before or at the entry of the cold season.
  • aqueous solution of the active ingredient is used for spraying.
  • the spraying solution may contain additional active ingredients to the compounds of the general formula (I), such as fungicides and materials aiding spraying.
  • the plants are sprayed with a spraying preparation containing a compound of the general formula (I) before or at the entry of the dry season.
  • the preparations according to the invention that can be used to increase the resistance of cultivated plants against weather extremities contain a compound of the general formula (I) in an amount of 0.001-95 % by mass, wherein the substituents are as defined above, and also agriculturally acceptable solid or liquid vehicles and/or auxiliary materials.
  • the preparation usually contains water as vehicle.
  • the aqueous solution of the active ingredient is preferably a concentrate which should be diluted with water before use to the concentration given above.
  • the aqueous solutions contain surfactants
  • the solutions for treating seeds contain materials aiding pelleting or pearling, for example film forming materials.
  • the dispersion media may contain agents improving adhesion or spreading, light protecting agents, if desired, stabilising agents and other additives as auxiliary agents.
  • water dilutable ULN concentrates, emulsifyable concentrates, wettable powders, soluble granulates or microgranulates can be prepared. These preparations preferably contain anionic or non-ionic detergents to assist dilution with water.
  • Solid preparations preferably contain kaolin, diatomaceous earth or dolomite, but may contain any other solid vehicle generally used in such products.
  • For preparing microgranulates preferably perlit is used as a vehicle.
  • the composition according to the invention can be applied together with other pesticides or can be even combined with them, provided that their active ingredient is compatible with the active ingredient of the composition according to the invention. In the case of such applications the treatment with a composition according to the invention does not require additional processes, it can be carried out together with other protective treatments of cultivated plants.
  • IR (KBr): 3360, 3320, 2910, 2400, 1720, 1650, 1430, 1390, 1250, 1230, 1120, 1040, 1015, 940, 895, 840, 825, 700, 640, 518 c f 1 .
  • IR (KBr): 3415, 3200, 3060, 2960, 2860, 2820, 1670, 1580, 1560, 1480, 1450, 1420, 1335, 1260, 1240, 1105, 1070, 1040, 1020, 1000, 970, 955, 900, 860, 800, 760, 700, 665, 645, 610, 590 cm- 1 .
  • IR (KBr): 3440, 2920, 2650, 2530, 2430, 1670, 1580, 1560, 1470, 1440, 1400, 1350, 1300, 1270, 1260, 1240, 1220, 1090, 1050, 1020, 1005, 960, 900, 890, 800, 750, 700, 680, 650, 580 cm -1 .
  • the desired amount of compound SIN-5 is dissolved completely in 1 M sodium hydrogen carbonate.
  • 4 % aqueous solution of polyvinyl-alcohol (PNA) is prepared.
  • PNA polyvinyl-alcohol
  • In case of pelleting (pearling) corn seed 1 ml of 4 % PNA solution is mixed with 1 ml solution containing SI ⁇ -5 in 5-15 mg/ml concentration. 200 corn seeds are dampened in the resulting 2 ml solution in Petri-dishes by shaking. Then the coated seeds are allowed to dry overnight at room temperature.
  • crops with smaller seed size e.g. rice
  • 1 ml of pearling agent containing 1-15 mg of SIN-5 agent is applied for coating 200 seeds.
  • Results signed by *, ** and *** are significantly differ from control sample, if *, p ⁇ 0.05, **, p ⁇ 0.01 and ***, pO.OOl, respectively.
  • the CSNT is developed to predict the minimal expectable germination ratio under extreme conditions.
  • the ratio of those seeds that will reliably and well gemrinate in cold spring weather is 90 % if they were proved high vigour by the CSNT, while this value is only 60 % if they showed low vigour under experimental stress conditions. This leads to the conclusion that if an active agent improves the vigour of the seedlings it in fact improves the germinating ratio of the seed on the arable soil at soil temperatures lower than the optimum.
  • Results signed by * are significant compared to control group if p ⁇ 0.05.
  • paprika and soya seeds were treated with aqueous SIN-5 solutions of different concentration before sowing.
  • DO control
  • Dl 1 mg of SIN-5/100 seeds
  • D2 2 mg of SIN-5/100 seeds
  • D3 3 mg of SIN-5/100 seeds
  • Doses applied on soya-beans DO: control; Dl: 2.5 mg of SIN-5/100 seeds; D2: 5 mg of SIN-5/100 seeds; D3: 10 mg of SIN- 5/100 seeds.
  • Paprika plants were grown in pots, in vegetable mould rich in humus, in growth chamber.
  • the growing conditions were the following: 16/8 h day /night period was applied together with a 25/20 °C thermal cycle. The intensity of the illumination was 220 ⁇ mol m "2 s "1 . Plants were watered daily. In the case of the soya-beans 25/18 °C thermal cycle was applied and the intensity of the illumination was 330 ⁇ mol m " s " . Watering was suspended for a few days after the appearance of flowers until the first signs of blighting were shown on the leaves. Then the leaves were sprayed with SIN-5, applied in 3 different doses.
  • the intensity of the 16-hour daily illumination was 220 ⁇ mol m '2 s "1 . Plants were sprayed with a 10 mg/1 concentration aqueous SIN-5 solution once at the age of 3 weeks. Before germination caryopses were pelleted: DO control; Dl: 5 mg SIN-5/100 seeds.
  • the compounds investigated were applied with coating onto the plant seeds, by treating 100 seeds with 1 ml coating agent containing 1 mg agent dissolved in 2 % aqueous PNA solution.
  • the size of the parcels was 9.2 m x 3.75 m, the density of the sowing was 5 seeds/m.
  • the experimental arrangement was randomised block design with four repeats. Plants were sowed 4-8 cm deep, depending on the moisture of the soil, in 30 cm distance between plants, with 45 cm row distance. The date of sowing was 8 May. The number of emerged plants was recorded.
  • Treatments with SIN-5 were carried out on commercially produced lands of two SC hybrid seeds. Female parent seeds and the plants twice during their development were treated. Compound SIN-5 was applied for coating seeds in the following concentrations:
  • Half dose 5 mg of SIN-5 dissolved in 2 ml of 2 % aqueous PVA solution per 100 seeds.
  • Double dose 20 mg of SIN-5 dissolved in 2 ml of 2 % aqueous PVA solution per 100 seeds.
  • Beside seed treatment plants were sprayed with the SIN-5-solution (50 mg of SIN-5 was dissolved in 2 1 water and this amount was used per parcel) before tasseling.
  • One parcel consisted of four 6 m long row. The distance of the rows was 91 cm. In the case of hybrids the distance between plants was 20 cm which corresponds to a density of 48-50000 plants/hectare. In the case of inbred lines the distance between plants was 16 cm which corresponds to a density of 60-62000 plants/hectare.
  • the biological value (germinating capability, vigour) of newly produced seeds is generally good. During storage the quality of the seed deteriorates first slowly and later with an increasing rate while its vitality also decreases. A stand originating from fresh seeds can produce even 10-15% more than that consisting of genetically identical and of the same number of plants but originating from aged seeds. Deterioration of germinating ability and vigour can be slowed with different procedures one of which could be a chemical treatment.
  • Spraying solution of the following composition is prepared: compound SIN-5 20 parts of weight sodium-laurilsulphate 3 parts of weight sodium-ligninsulphonate 6 parts of weight water 63 parts of weight kaolin 8 parts of weight
  • Spraying solution of the following composition is prepared: compound SIN-5 20 parts of weight alkyl-arylsulphonate 5 parts of weight water 75 parts of weight
  • Coating agent of the following composition is prepared: compound SIN-5 0.25 parts of weight 2 % aqueous solution of polyvinyl-alcohol 99.75 parts of weight
  • the coating agent is applied in 0.01-0.02 % by mass of the seed.
  • a granulate of the following composition is prepared: compound SIN-5 10 parts of weight limestone grist 64 parts of weight ethyleneglycol 3 parts of weight high dispersity silicic acid 4 parts of weight sodium-ligninsulphonate 4 parts of weight water 15 parts of weight
  • the mixture of the components is grinded in a hammering mill to a grain size of less then 5 ⁇ m.
  • a powder composition of the following composition is prepared:
  • SIN-5 compound 50 parts of weight polyvinylpyrrolidon 10 parts of weight silicondioxide 25 parts of weight porcelain clay 15 parts of weight
  • a powder composition of the following composition is prepared:
  • SIN-5 compound 50 parts of weight calcium-ligninsulphonate 5 parts of weight isopropylnaphtalenesulphonate 1 parts of weight silicondioxide 4 parts of weight filling material (kaolin) 40 parts of weight
PCT/HU2001/000152 2000-12-22 2001-12-20 Derivatives of acetic acid for increasing abiotic stress tolerance of cultivated plants WO2002051811A1 (en)

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HU0005002A HUP0005002A2 (en) 2000-12-22 2000-12-22 Acetic acid derivatives, compositions containing the same their use for increasing the abiotic stress tolerance of cultivated plants, for inhibiting the aging of seeds and for increasing the seed-vigore during stress conditions
HUP0005002 2000-12-22

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2255626A1 (de) * 2009-05-27 2010-12-01 Bayer CropScience AG Verwendung von Succinat Dehydrogenase Inhibitoren zur Steigerung der Resistenz von Pflanzen oder Pflanzenteilen gegenüber abiotischem Stress

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Publication number Priority date Publication date Assignee Title
CN113979799B (zh) * 2021-10-21 2023-02-24 华中农业大学 一种提高耐渍性的种子包衣组合物及其制备方法和应用

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DE2640484A1 (de) * 1975-09-11 1977-04-07 Philagro Sa Amidoxim-derivate, ihre herstellung und verwendung
DE2808317A1 (de) * 1977-03-02 1978-09-07 Ciba Geigy Ag Pflanzenwuchsfoerdernde und pflanzenschuetzende mittel auf basis von oximaethern und -estern
JPH026453A (ja) * 1988-06-27 1990-01-10 Nippon Soda Co Ltd アミジン誘導体、その製造方法及び殺ダニ剤・農園芸用殺菌剤
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DE2640484A1 (de) * 1975-09-11 1977-04-07 Philagro Sa Amidoxim-derivate, ihre herstellung und verwendung
DE2808317A1 (de) * 1977-03-02 1978-09-07 Ciba Geigy Ag Pflanzenwuchsfoerdernde und pflanzenschuetzende mittel auf basis von oximaethern und -estern
JPH026453A (ja) * 1988-06-27 1990-01-10 Nippon Soda Co Ltd アミジン誘導体、その製造方法及び殺ダニ剤・農園芸用殺菌剤
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2255626A1 (de) * 2009-05-27 2010-12-01 Bayer CropScience AG Verwendung von Succinat Dehydrogenase Inhibitoren zur Steigerung der Resistenz von Pflanzen oder Pflanzenteilen gegenüber abiotischem Stress
WO2010136139A3 (de) * 2009-05-27 2011-06-30 Bayer Cropscience Aktiengesellschaft Verwendung von succinat dehydrogenase inhibitoren zur steigerung der resistenz von pflanzen oder pflanzenteilen gegenüber abiotischem stress

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