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WO2009095098A2 - Utilisation de benzothiadiazoles - Google Patents

Utilisation de benzothiadiazoles Download PDF

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Publication number
WO2009095098A2
WO2009095098A2 PCT/EP2008/064722 EP2008064722W WO2009095098A2 WO 2009095098 A2 WO2009095098 A2 WO 2009095098A2 EP 2008064722 W EP2008064722 W EP 2008064722W WO 2009095098 A2 WO2009095098 A2 WO 2009095098A2
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group
alkyl
substituted
halogen
hydrogen
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WO2009095098A3 (fr
Inventor
Uwe Conrath
Gudrun Schmitz
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Rheinisch Westlische Technische Hochschuke RWTH
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Rheinisch Westlische Technische Hochschuke RWTH
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms

Definitions

  • the present invention relates to the use of benzothiadiazoles as a protection against the effects of abiotic stress on plants.
  • Abiotic stresses such as drought, salt or extreme temperatures limit crop production significantly.
  • abiotic stress often causes reductions in overall crop yield or decreases in the quality of plants.
  • Crop losses and crop yield losses of major agricultural crops by abiotic stress represent a significant economic factor.
  • temperature stress such as chill, frost or heat and effects such as dryness or drought are major limiting factors of plant growth and productivity.
  • Plants often are exposed to cold, for example to temperatures below freezing after sowing. Freezing temperatures often cause plants to stall or suffer enduring damages. Particularly with regard to agricultural crop damages due to frost often cause immense losses in agriculture.
  • benzothiadiazoles furthermore can be used to protect plants against the effects of abiotic stress, especially of frost and drought.
  • UD 40102 / SAM AL Therefore, the object underlying the present invention was to provide a novel use of benzothiadiazoles.
  • X is selected from the group comprising hydrogen, halogen, hydroxy, methyl, methoxy and/or COOH;
  • Y is selected from the group comprising hydrogen, halogen, SO 3 H, nitro, hydroxy, and/or amino;
  • Z is selected from the group comprising cyano and/or -CO-A
  • U is selected from the group comprising oxygen and/or sulfur
  • U 1 is selected from the group comprising oxygen and/or -N(R 5 )-;
  • R is selected from the group comprising hydrogen, d-Cg-alkyl, d-Cg-alkyl that is substituted by halogen, cyano, nitro, hydroxy, U-Ci-C3-alkyl or by C2-C4- dialkylamino or is interrupted by the CO group, (T)-COOH or (T)COOCi-C 4 - alkyl, Cs-C ⁇ -alkenyl, halo-substituted Cs-C ⁇ -alkenyl, Cs-C ⁇ -alkynyl, halo- substituted Cs-C ⁇ -alkynyl, (T) n C3-C8-cycloalkyl, and/or a group selected from the group comprising
  • X a , X b and X c are each independently of each other selected from the group comprising hydrogen, halogen, hydroxy, cyano, COOH, Ci-C3-alkyl-OOC, C 1 - C 4 -alkyl, Ci-C 4 -alkoxy, and/or Ci-C 2 -haloalkyl having up to 5 halogen atoms, particularly fluorine atoms; or
  • X a is selected from the group comprising Ci-C2-halogenalkoxy having up to 5 halogen atoms, nitro, dimethylamino, phenyl, phenyloxy, benzyloxy, sulfamoyl and X b and X c are both hydrogen; or
  • X a is selected from the group comprising phenyl, phenyloxy and/or benzyloxy and X b is selected from the group comprising halogen and/or methyl and X c is hydrogen; or
  • X a , X b and X c together are 4 or 5 fluorine atoms; napht is a naphthyl radical that is unsubstituted or is substituted by halogen, methyl, methoxy or by nitro;
  • W is a 5- to 7-membered saturated or unsaturated heterocycle having from 1 to 3 hetero atoms selected from the group comprising O, N and S that is unsubstituted or is substituted by halogen, trifluoromethyl, cyano, Ci-C2-alkyl or by a C 1 -C 2 - alkoxycarbonyl-C2-C4-alkyleneimino radical, or is a monosaccharide radical; - A -
  • T is a bridge member selected from the group comprising -CH 2 -, -CH 2 CH 2 -, -CH(CH 3 )-, -CCH 3 (CH 3 )-, -CH 2 CH 2 CH 2 -, and/or -CH 2 CH 2 O-;
  • R 1 is selected from the group comprising hydrogen, Ci-Cs-alkyl, Ci-Cs-alkyl interrupted by an oxygen or sulfur atom, Ci-Cs-alkyl substituted by halogen, cyano, COOH or by Ci-C 2 -alkyl-OOC, Ci-Cs-alkyl interrupted by an oxygen or sulfur atom and substituted by halogen, cyano, COOH or by Ci-C 2 -alkyl-OOC, C 3 -C 5 -alkenyl, C 3 -C 5 -alkenyl substituted by Ci-C 3 -alkyl-OOC, C 3 -C 5 -alkynyl, C 3 -C 5 -alkynyl substituted by Ci-C 3 -alkyl-OOC, (T) n -C 3 -C 6 -cycloalkyl, (T) n -C 3 - C ⁇ -cycloalkyl substituted by Ci-C 3 -alkyl
  • R 2 is selected from the group comprising hydrogen, hydroxy, Ci-C 3 -alkyl, Ci-C 3 - alkyl substituted by cyano or Ci-C 3 -alkoxy, Ci-C4-alkoxy, a 3- to 6-membered saturated or unsaturated heterocycle containing O, N or S as hetero atoms;
  • R 1 and R 2 together with the atom to which they bond are a heterocycle W;
  • R 3 is selected from the group comprising hydrogen, cyano, Ci-C ⁇ -alkyl, phenyl, phenyl substituted by halogen, hydroxy, methyl, methoxy or COOH, and/or a heterocycle W;
  • R 4 is selected from the group comprising hydrogen, Ci-C ⁇ -alkyl, CONH 2 , CONH-
  • Ci-C 3 -alkanoyl Ci-C 3 -alkanoyl substituted by halogen or by Ci-C 3 -alkoxy, C 3 -Cs-alkenoyl and/or C 3 -Cs-alkenoyl substituted by halogen or by Ci-C 3 -alkoxy;
  • R 3 and R 4 together with the atom to which they bond are a heterocycle W or a carbocyclic ring W;
  • W is a carbocyclic radical having from 3 to 7 ring carbon atoms
  • R 5 is selected from the group comprising hydrogen and/or methyl
  • R 6 is selected from the group comprising hydrogen and/or Ci-C 4 -alkyl; n is O or 1. Furthermore, the invention relates to a composition for improving tolerance of a plant against abiotic stress, comprising a compound applicable in accordance with the invention as an active ingredient.
  • a singular application of a compound applicable according to the invention can improve the tolerance of a plant against abiotic stresses, especially against frost or drought.
  • a singular application of a compound applicable according to the invention already can provide a tolerance of the plant against cold lasting several days, weeks or months.
  • plants refers to all genera and species of higher and lower plants of the plant kingdom.
  • plants includes the mature plants, seed, shoots and seedlings, and also parts, such as tubers, seeds or fruits, plant organs, tissues, protoplasts, callus and other cultures, for example cell cultures, derived therefrom.
  • mature plants refers to plants at any developmental stage beyond that of the seedling.
  • seedling refers to a young immature plant at an early developmental stage.
  • Abiotic stress acting on a plant are for example temperature effects such as chill, frost or heat, effects of water such as dryness, drought, wet conditions, or chemical load such as lack of or excess of nutrients, mineral salts, heavy metals, nitrogen or oxygen and/or UV radiation.
  • the abiotic stress is selected from the group comprising drought stress, salinity stress, heat stress, cold stress, frost stress, low nitrogen conditions, low oxygen conditions, low nutrient conditions and/or UV radiation. It is an surprising advantage that the application of compounds according to general formula (I) can improve the tolerance of plants against abiotic stress factors, preferably against abiotic stress selected from the group comprising drought stress, salinity stress, cold or heat stress, and/or frost stress.
  • an improved tolerance of a plant against abiotic stress such as cold
  • an improved stability or resistance against abiotic stress such as cold
  • An improved resistance or tolerance against cold can provide the advantage that damages to a plant caused by frost or cold can be reduced or inhibited.
  • Such resistance against stress factors such as cold
  • Such resistance against stress factors particularly can be understood as an induction of a tolerance against stress factors, such as cold, in a plant.
  • Temperature ranges in which the compounds applicable according to the invention can provide and/or activate a protection of plants against cold are for example in the range from > - 14°C to ⁇ 10 0 C, preferably in the range from > - 14 0 C to ⁇ 4 0 C, more preferably in the range from > - 14 0 C to ⁇ 0 0 C.
  • hetero atoms also includes elements other than N, O and S, for example Si or P.
  • halogen according to the invention is to be understood as meaning fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine.
  • alkyl according to the invention is to be understood as meaning straight-chain or branched alkyl groups.
  • Preferred alkyl groups are selected from the group comprising methyl, ethyl and the isomers of propyl, butyl, pentyl, hexyl, heptyl or octyl, such as, for example, isopropyl, isobutyl, tert.-butyl, sec. -butyl and/or isopentyl.
  • cycloalkyl according to the invention is to be understood as meaning for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • alkenyl according to the invention is to be understood as meaning propen-1-yl, allyl, buten-1-yl, buten-2-yl or buten-3-yl, and chains having several double bonds.
  • alkynyl according to the invention is to be understood as meaning for example propyn-2-yl, butyn-1-yl, butyn-2-yl, pentyn-4-yl, preferably propargyl.
  • heterocycles according to the invention is to be understood as being, for example furan, tetrahydrofuran, thiophene, tetrahydropyran, pyrrole, pyrrolidine, imidazole, 1,2,4- triazole, piperidine, pyridine, pyrimidine, morpholine or azacyclo heptane.
  • Preferred heterocycles are selected from the group comprising furan-2-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-2-yl, l,3-dioxolan-5-yl, pyrrol- 1-yl, pyrrol-2-yl, pyrrolidin-1-yl, isoxazol-3-yl, isoxazol-4-yl, l,2-di-thiazolin-5-yl, imidazol-1-yl, 1,2,4- triazol-1-yl, 1,3,4-triazol-l-yl, thiophen-2-yl, piperidin-1-yl, piperidin-4-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, morpholin-1-
  • glycode radical is to be understood as being, for example, glucopyranosyl, galactopyranosyl, allofuranosyl or mannityl, the OH groups being free or acetylated or etherif ⁇ ed by methyl, benzyl or by isopropylidenyl.
  • the diisopropylidenyl derivatives are preferred, whilst of these in turn the following radicals selected from the group comprising diacetone-D-glucosidyl, 1,2,3,4-di-O-isopropyl-idene-D- galactopyranos-6-yl, 1 ,2,5,6-di-O-isopropylidene-D-mannit-3-yl, 1 ,2,5,6-di-O- isopropylidene-alpha-D-allofuranos-3-yl, D-glucofuranos-3-yl, D-galacto-pyranos-6-yl, D- mannit-3-yl, D-allofuranos-4-yl, mannopyranos-1-yl, 2-methyl-D-glucosid-6-yl, 1,2,5,6- tetraacetyl-D-galactopyranos-3-yl and/or 2,3,5-tria
  • preferred salts of the compounds according to general formula (I) comprise salts of the phytophysio logically tolerable 7-carboxylic acid with primary, secondary or tertiary amines or with inorganic bases.
  • Suitable cationic radicals for the compounds applicable according to the invention are for example metals and organic bases.
  • Alkali metals and alkaline earth metals are advantageous as metals, but any others may also come into consideration.
  • Suitable organic bases are amines, especially having aliphatic, aromatic, araliphatic and/or cycloaliphatic radicals.
  • Preferred cationic groups are for example cations of alkali metals, preferably selected from the group comprising Li + , Na + and/or K + , or cations of alkali earth metals, preferably selected from the group comprising Ca 2+ and/or Mg 2+ .
  • Further preferred cationic groups are for example quaternary ammonium salts which contain at least one nitrogen atom having four substitutes, wherein the substitutes preferably are selected from the group comprising H and/or Ci-Cs-alkyl radical.
  • Examples for ammonium cations are selected from the group comprising tetramethylammonium, tetraethylammonium, and/or tetra-n-butylammonium.
  • Suitable bases or compounds having basic character are inorganic bases or base formers, for example selected from the group comprising hydroxides, carbonates and/or hydrogen carbonates of alkali metals and alkaline earth metals, preferably LiOH, NaOH, KOH, Mg(OH) 2 or Ca(OH) 2 , and also NaHCO 3 , KHCO 3 , Na 2 CO 3 or K 2 CO 3 .
  • Salt-forming amines preferably are selected from the group comprising trimethylamine, triethylamine, tripropylamine, tributylamine, tribenzylamine, tricyclohexylamine, triamylamine, trihexylamine, N,N-dimethylaniline, N,N-dimethyltoluidine, N,N-dimethyl-p- aminopyridine, N-methylpyrrolidine, N-methylpiperidine, N-methylpyrrolidine, N- methylimidazole, N-methylpyrrole, N-methylmorpholine, N-methylhexamethyleneimine, pyridine, quinoline, alpha-picoline, beta-picoline, isoquinoline, pyrimidine, acridine, N,N,N',N'-tetramethylethylenediamine, N,N,N',N'-tetraethylethylenediamine, quinoxaline, N- propyldiisopropylamine,
  • Preferred compounds are selected from the group comprising benzo- 1,2,3- thiadiazolecarboxylic acid, benzo-l,2,3-thiadiazolethiocarboxylic acid, cyanobenzo- 1,2,3- thiadiazole, Benzo-l,2,3-thiadiazolecarboxylic acid amide, benzo-l,2,3-thiadiazolecarboxylic acid hydrazide, benzo-l,2,3-thiadiazole-7-carboxylic acid, benzo- 1,2, 3-thiadiazole-7- thiocarboxylic acid, 7-cyanobenzo-l,2,3-thiadiazole, benzo- l,2,3-thiadiazole-7-thiocarboxylic acid-S-methyl ester, benzo-l,2,3-thiadiazole-7-carboxylic acid amide, benzo- 1,2,3- thiadiazole-7-carboxylic acid hydrazide, alkyl benzo- 1,2,3-thiadia
  • the substituents X and Y are hydrogen.
  • the substituent Z is a group COA.
  • the substituent A is a group UR, wherein U is selected from the group comprising oxygen and/or sulphur. Preferably, U is sulphur.
  • the substituent R is selected from the group comprising hydrogen, Ci-Cs-alkyl, Ci-Cs-alkyl that is substituted by halogen, or by Ci-C3-alkoxy, Cs-C ⁇ -alkenyl, Cs-C ⁇ -alkenyl substituted by halogen, Cs-C ⁇ -alkynyl, Cs-C ⁇ -alkynyl substituted by halogen, benzyl, halo-substituted benzyl, and/or benzylmethoxy.
  • R selected from the group comprising hydrogen, d-Cg-alkyl, d-Cg-alkyl that is substituted by halogen or by Ci-C 3 -alkoxy, Cs-C ⁇ -alkenyl, Cs-C ⁇ -alkenyl substituted by halogen, Cs-C ⁇ -alkynyl, Cs-C ⁇ -alkynyl substituted by halogen, benzyl, halo-substituted benzyl, and/or benzylmethoxy.
  • the group COA is a group C0S(Ci-C 8 -alkyl).
  • the compounds are selected from the group comprising benzo-l,2,3-thiadiazole-7-carboxylic acid, benzo-l,2,3-thiadiazole-7-thiocarboxylic acid and/or their Ci-Cs-alkyl esters.
  • the d-Cg-alkyl ester is selected from the group comprising methyl ester, ethyl ester, isopropyl ester, n-butyl ester, tert-butyl ester, n-pentyl ester, n-hexyl ester, n-heptyl ester and/or n-octyl ester.
  • Ci-C 4 -alkyl esters particularly selected from the group comprising methyl ester, ethyl ester, isopropyl ester and/or tert-butyl ester.
  • methyl ester and ethyl ester are particularly preferred.
  • the compounds are selected from the group comprising benzo-l,2,3-thiadiazole-7- thiocarboxylic acid and/or its S-Ci-Cs-alkyl esters.
  • the S-Ci-Cs-alkyl esters are S-Ci-C4-alkyl esters selected from the group comprising S-methyl ester, S-ethyl ester, S-isopropyl ester and/or S-tert-butyl ester. Especially preferred are S-methyl ester and S-ethyl ester.
  • the compound is benzo-l,2,3-thiadiazole-7-thiocarboxylic acid-S-methyl ester.
  • a particularly preferred applicable compound has a structure according to general formula (II) as given as follows:
  • Preferred plants are selected from the group comprising cereals, beet, pomes, drupes and soft fruit, leguminous plants, oil plants, cucumber plants, fibre plants, citrus fruit, vegetables, lauraceae, or plants such as maize, tobacco, nuts, coffee, sugar cane, tea, vines, hops, bananas and natural rubber plants, and/or ornamentals.
  • Preferred cereals are selected from the group comprising wheat, barley, rye, oats, rice, spelt, flax seed, sorghum and/or related crops.
  • Preferred beet are selected from the group comprising sugar beet and/or fodder beet.
  • Preferred pomes, drupes and soft fruit are selected from the group comprising apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blueberries and/or blackberries.
  • Preferred leguminous plants are selected from the group comprising beans, lentils, peas, and/or soybeans.
  • Preferred oil plants are selected from the group comprising rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans, and/or groundnuts.
  • Preferred cucumber plants are selected from the group comprising cucumber, marrows, and/or melons.
  • Preferred fibre plants are selected from the group comprising cotton, flax, hemp and/or jute.
  • Preferred citrus fruit are selected from the group comprising oranges, lemons, grapefruit, and/or mandarins.
  • Preferred vegetables are selected from the group comprising spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes and/or paprika.
  • Preferred lauraceae are selected from the group comprising avocados, cinnamon and/or camphor.
  • Preferred ornamentals are selected from the group comprising flowers, shrubs, deciduous trees and/or conifers. In preferred embodiments the plants are selected from the group comprising cereals, fruit plants and/or vegetables.
  • Agricultural crops which are particularly suitable target crops for the application of the compounds according to the invention are selected from the group comprising cucumbers, tobacco, vines, rice, cereals, for example wheat, pears, pepper, potatoes, tomatoes and/or apples.
  • Further agricultural crops which are particularly suitable target crops for the application of the compounds applicable according to the invention are selected from the group comprising cotton, vegetables for example cucumber or beans, barley, grass, oats, coffee, maize, fruit plants, rice, rye, soybeans, vines, wheat, ornamentals, sugar cane and/or a plurality of seeds.
  • Particularly suitable cereals are selected from the group comprising barley, oats, rye and/or wheat.
  • Particularly suitable fruit plants are selected from the group comprising fruit trees, vines, soft fruit, berries, strawberries, blueberries and/or raspberries
  • Particularly suitable fruit trees are selected from the group comprising apple trees, pear trees, cherry trees, plum trees, prune plum trees, apricot trees and/or peach trees.
  • the present invention relates also to the use of the compounds applicable according to the invention to manufacture a composition particularly a composition for improving tolerance of a plant against abiotic stress, preferably for improving frost tolerance and/or tolerance against drought.
  • said composition comprises as an active ingredient a compound applicable according to the invention, particularly selected from the group comprising benzo- l,2,3-thiadiazole-7-thiocarboxylic acid and/or its S-Ci-Cs-alkylesters.
  • said composition comprises as an active ingredient benzo-l,2,3-thiadiazole-7-thiocarboxylic acid and/or its S-Ci-Cs-alkylesters.
  • said composition comprises as an active ingredient benzo-l,2,3-thiadiazole-7-thiocarboxylic acid-S-methyl ester.
  • said composition is formulated as a liquid, gel or solid form formulation.
  • the compounds according to general formula (I) are normally applied in the form of compositions and can be applied to the plant or to the surrounding thereof, simultaneously or in succession, with further compounds.
  • These further compounds can be fertilisers or micronutrient donors or other preparations that influence plant growth. They can also be selective herbicides, insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or application-promoting adjuvants customarily employed in the art of formulation.
  • Suitable carriers and adjuvants can be solid or liquid and correspond to the substances ordinarily employed in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackif ⁇ ers, thickeners, binders or fertilisers.
  • a preferred method of applying a compound according to general formula (I), or an agrochemical composition which contains at least one of said compounds, is foliar application.
  • the compounds according to general formula (I) can also penetrate the plant through the roots via the soil (systemic action) if the locus of the plant is impregnated with a liquid formulation, or if the compounds are applied in solid form to the soil, e.g. in granular form (soil application).
  • the compounds according to general formula (I) may, however, also be applied to seeds (coating) by impregnating the seeds either with a liquid formulation containing a compound according general formula (I), or coating them with a solid formulation (dressing).
  • other methods of application may be possible, for example the specific treatment of the plant stem or buds.
  • the compounds according to general formula (I) are used in unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation.
  • compounds according to general formula (I) are formulated in known manner e.g. into emulsif ⁇ able concentrates, coatable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations in e.g. polymer substances.
  • the methods of application such as spraying, atomising, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.
  • Advantageous rates of application are normally from 30 g to 5 kg of the compound applicable according to the invention per hectare, preferably from 100 g to 2 kg compound per hectare, most preferably from 100 g to 600 g compound per hectare.
  • compositions i.e. the compositions, preparations or mixtures containing the compound according to general formula (I) as active ingredient and, where appropriate, a solid or liquid adjuvant
  • extenders e.g. solvents, solid carriers and, where appropriate, surface-active compounds (surfactants).
  • Suitable solvents are for example aromatic hydrocarbons, preferably the fractions containing 8 to 12 carbon atoms, e.g.
  • xylene mixtures or substituted naphthalenes phthalates such as dibutyl phthalate or dioctyl phthalate, aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols and glycols and their ethers and esters, such as ethanol, ethylene glycol, ethylene glycol monomethyl or monoethyl ether, ketones such as cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethylformamide, as well as vegetable oils or epoxidised vegetable oils, such as epoxidised coconut oil or soybean oil; or water.
  • phthalates such as dibutyl phthalate or dioctyl phthalate
  • aliphatic hydrocarbons such as cyclohexane or paraffins
  • alcohols and glycols and their ethers and esters such as ethanol, ethylene glycol, ethylene glycol monomethyl or monoe
  • the solid carriers used e.g. for dusts and dispersible powders are normally natural mineral fillers such as calcite, talcum, kaolin, montmorillonite or attapulgite.
  • Suitable granulated adsorptive carriers are porous types, for example pumice, broken brick, sepiolite or bentonite, and suitable nonsorbent carriers are, for example, calcite or sand.
  • a great number of pregranulated materials of inorganic or organic nature can be used, e.g. especially dolomite or pulverised plant residues.
  • Particularly advantageous application-promoting adjuvants are also natural (animal or vegetable) or synthetic phospholipids of the series of the cephalins and lecithins.
  • suitable surface-active compounds are non-ionic, cationic and/or anionic surfactants having good emulsifying, dispersing and wetting properties.
  • surfactants is also understood as comprising mixtures of surfactants.
  • Cationic surfactants are preferably quaternary ammonium salts which contain, as N- substituent, at least one Cs -C22 alkyl radical and, as further substituents, unsubstituted or halogenated lower alkyl, benzyl or hydroxy-lower alkyl radicals.
  • the term "lower alkyl” according to the invention is to be understood as meaning particularly C 1 -C 8 alkyl radicals.
  • Suitable soaps are the alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts of higher fatty acids Of CiO-C 22 , e.g. the sodium or potassium salts of oleic or stearic acid or of natural fatty acid mixtures which can be obtained e.g. from coconut oil or tallow oil.
  • Synthetic surfactants that may be used are especially fatty alcohol sulfonates, fatty alcohol sulfates, sulfonated benzimidazole derivatives or alkylsulfonates.
  • the fatty alcohol sulfonates or sulfates are usually in the form of alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts and contain a Cs-C 22 alkyl radical.
  • Non- ionic surfactants are preferably polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, said derivatives containing 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon moiety and 6 to 18 carbon atoms in the alkyl moiety of the alkylphenols.
  • compositions may also contain further auxiliaries such as stabilisers, antifoams, viscosity regulators, binders, tackif ⁇ ers as well as fertilisers or other active ingredients for obtaining special effects.
  • auxiliaries such as stabilisers, antifoams, viscosity regulators, binders, tackif ⁇ ers as well as fertilisers or other active ingredients for obtaining special effects.
  • Agrochemical compositions preferably contain 10 % by weight to 90 % by weight, preferably 30 % by weight to 80 % by weight, particularly 50 % by weight to 60 % by weight, relating to the total weight of the agrochemical composition, of a compound according to formula (I).
  • the present invention relates also to a method for improving the resistance of a plant against abiotic stress, preferably for improving frost tolerance and/or tolerance against drought, wherein a compound according applicable to the invention is administered as an active ingredient to a plant and/or its surrounding.
  • benzo-l,2,3-thiadiazole-7-thiocarboxylic acid-S- methyl ester is administered as an active ingredient to a plant and/or its surrounding.
  • each of the herbaceous plant thale cress (botanical name: Arabidopsis thaliana) were distributed on potting soil (392 cm 3 , potting soil of Balster, Fr ⁇ ndenberg, Germany) in flower pots (7x7x 8cm, G ⁇ ttinger). Germination of the seeds was initiated by a stratification of 2 days at 4°C in the dark. Following, the plants were grown at 20 0 C, 65 % relative humidity, and 8 hours light per day in a growing chamber (approx. 3x5 m, York International). The plants were watered as necessary until the soil became evenly moist.
  • the plant tissue was initially frozen in liquid nitrogen and stored at -80 0 C in a freezer (Model C660 Premium, New Brunswick Scientific, Edison, NJ, USA) until further processing of the collected tissues.
  • the final concentration of the gene specific primers was 0.2 ⁇ M each. 2 ⁇ l of the diluted cDNA were used as template.
  • the conditions of the PCR reactions were as follows: An initial activation step for the polymerase was performed at 95°C for 10 minutes. Following, 40 amplification cycles at 95°C for 15 seconds each and an incubation at 60 0 C for 1 minute were performed. The Real-time DNA amplification was recorded and analysed by the software ABI PRISM 7000 SDS 1.0 Software (Applied Biosystems, Foster City, CA, USA). The expression of the gene coding for Actin2 was used as in internal standard for adjusting to minor differences in the amount of the DNA templates.
  • control plants Before treatment with 100 ⁇ M of benzo-l,2,3-thiadiazole-7-thiocarboxylic acid-S-methyl ester, control plants showed ca. 5% expression of the gene coding for the alternative oxidase Ia (AOXIa), relating to a relative graduation of 0 % to 100%.
  • AOXIa alternative oxidase Ia
  • the expression of AOXIa in the control plants increased only marginally to about 8%, 10%, and 8 % on the first, second, and third day, respectively, after treatment with benzo-l,2,3-thiadiazole-7-thiocarboxylic acid-S- methyl ester.
  • benzo-l,2,3-thiadiazole-7-thiocarboxylic acid-S-methyl ester induces the expression of the gene coding for alternative oxidase Ia (AOXIa) in thale cress. It is assumed that the gene product is involved in an increased production of heat and the frost tolerance in thale cress induced by benzo-l,2,3-thiadiazole-7-thiocarboxylic acid-S-methyl ester.
  • thale cress (scientific name: Arabidopsis thaliana) were distributed on potting soil (392 cm 3 , potting soil of Balster, Fr ⁇ ndenberg, Germany) in flower pots (7x7x8cm, G ⁇ ttinger). Germination of the seeds was initiated by stratification for 2 days at 4°C in the dark. Following, the plants were grown at 20 0 C, 65 % relative humidity, and 8 hours light per day in a growing chamber (approx. 3x5 m, York International). The plants were watered as necessary until the soil became evenly moist. On the day before treatment with benzo-l,2,3-thiadiazole-7-thiocarboxylic acid-S-methyl ester, the plants were watered for the last time and excess water was removed immediately before treatment.
  • the plants in 2 pots each were evenly sprayed with 1 ml of an aqueous solution of Bion® (Syngenta) containing 100 ⁇ M of benzo- l,2,3-thiadiazole-7-thiocarboxylic acid-S-methyl ester.
  • Another pot of plants received control treatment with 1 ml of an aqueous solution of Bion® containing all components in the same concentration as used for the treatment, except for benzo-l,2,3-thiadiazole-7-thiocarboxylic acid- S -methyl ester.
  • the solution was made by dissolving the active ingredient and formulation without active ingredient, respectively, in mains water using a laboratory mixer.
  • the plants were kept for 18 days in the growing chamber at 20 0 C, and 8 hours light per day with 65 % relative humidity. During this 18-day-period the plants were not watered at all. After 18 days the appearance of the plants was evaluated.

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  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pretreatment Of Seeds And Plants (AREA)

Abstract

La présente invention concerne l'utilisation de composés de formule générale (I), et notamment de benzothiadiazoles, comme protection contre les effets du stress abiotique sur les plantes.
PCT/EP2008/064722 2008-01-29 2008-10-30 Utilisation de benzothiadiazoles Ceased WO2009095098A2 (fr)

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DE102008006622.2 2008-01-29
DE102008006622A DE102008006622A1 (de) 2008-01-29 2008-01-29 Verwendung von Benzothiadiazolen

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WO2009095098A2 true WO2009095098A2 (fr) 2009-08-06
WO2009095098A3 WO2009095098A3 (fr) 2009-11-05

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2392210A1 (fr) * 2010-06-04 2011-12-07 Syngenta Participations AG Méthodes pour améliorer la tolérance des plantes au stress
WO2016073301A1 (fr) * 2014-11-03 2016-05-12 Syngenta Participations Ag Procédé pour améliorer la tolérance au stress abiotique du gazon
US9770028B1 (en) 2012-04-13 2017-09-26 Syngenta Participations Ag Method of improving turfgrass abiotic stress tolerance
US10517298B1 (en) 2012-04-13 2019-12-31 Syngenta Participations Ag Method of controlling phytopathogenic diseases on turfgrass
US10524474B1 (en) 2012-04-12 2020-01-07 Syngenta Participations Ag Method of controlling phytopathogenic diseases on turfgrass
US10568327B1 (en) 2012-04-12 2020-02-25 Syngenta Participations Ag Method of controlling phytopathogenic diseases on turfgrass
US11006632B2 (en) 2015-07-28 2021-05-18 Adam Mickiewicz University Foundation Application of 7-carboxybenzo[1,2,3]thiadiazole amides as plant stimulants

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GB1176799A (en) * 1966-10-21 1970-01-07 Shell Int Research Novel Biocides and their preparation
ATE82668T1 (de) 1987-08-21 1992-12-15 Ciba Geigy Ag Benzothiadiazole und ihre verwendung in verfahren und mitteln gegen pflanzenkrankheiten.
JPH0814471B2 (ja) * 1987-09-09 1996-02-14 三菱電機株式会社 誘導装置
ATE109139T1 (de) * 1989-03-08 1994-08-15 Ciba Geigy Ag Mittel zum schutz von pflanzen gegen krankheiten.
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ES2250658T3 (es) * 2001-07-02 2006-04-16 Ustav Organicke Chemie A Biochemie Akademie Ved Ceske Republiky El uso de 2-alfa, 3-alfa, 17-beta-trihidroxi-5-alfa-androstan-6-ona para el desarrollo de plantas disminuyendo el estres de la planta.

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2392210A1 (fr) * 2010-06-04 2011-12-07 Syngenta Participations AG Méthodes pour améliorer la tolérance des plantes au stress
US10524474B1 (en) 2012-04-12 2020-01-07 Syngenta Participations Ag Method of controlling phytopathogenic diseases on turfgrass
US10568327B1 (en) 2012-04-12 2020-02-25 Syngenta Participations Ag Method of controlling phytopathogenic diseases on turfgrass
US10555525B2 (en) 2012-04-13 2020-02-11 Syngenta Participations Ag Method of improving turfgrass abiotic stress tolerance
US9770028B1 (en) 2012-04-13 2017-09-26 Syngenta Participations Ag Method of improving turfgrass abiotic stress tolerance
US11737464B2 (en) 2012-04-13 2023-08-29 Syngenta Participations Ag Method of improving turfgrass abiotic stress tolerance
US10517298B1 (en) 2012-04-13 2019-12-31 Syngenta Participations Ag Method of controlling phytopathogenic diseases on turfgrass
US11234440B2 (en) 2012-04-13 2022-02-01 Syngenta Participations Ag Method for improving turfgrass abiotic stress tolerance
AU2015343427B2 (en) * 2014-11-03 2020-03-12 Syngenta Crop Protection Ag Method for improving turfgrass abiotic stress tolerance
WO2016073301A1 (fr) * 2014-11-03 2016-05-12 Syngenta Participations Ag Procédé pour améliorer la tolérance au stress abiotique du gazon
KR20170078692A (ko) * 2014-11-03 2017-07-07 신젠타 파티서페이션즈 아게 잔디 비생물 스트레스 관용성의 개선 방법
CN107072208A (zh) * 2014-11-03 2017-08-18 先正达参股股份有限公司 改进草坪草非生物胁迫耐受性的方法
US11395491B2 (en) 2014-11-03 2022-07-26 Syngenta Participations Ag Method for improving turfgrass abiotic stress tolerance
KR102551159B1 (ko) 2014-11-03 2023-07-03 신젠타 파티서페이션즈 아게 잔디 비생물 스트레스 관용성의 개선 방법
JP2017533219A (ja) * 2014-11-03 2017-11-09 シンジェンタ パーティシペーションズ アーゲー 芝草の非生物的ストレス耐性を向上させる方法
CN117561934A (zh) * 2014-11-03 2024-02-20 先正达参股股份有限公司 改进草坪草非生物胁迫耐受性的方法
US11006632B2 (en) 2015-07-28 2021-05-18 Adam Mickiewicz University Foundation Application of 7-carboxybenzo[1,2,3]thiadiazole amides as plant stimulants

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DE102008006622A1 (de) 2009-07-30

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