WO2000000031A1 - Herbizides mittel - Google Patents
Herbizides mittel Download PDFInfo
- Publication number
- WO2000000031A1 WO2000000031A1 PCT/EP1999/004374 EP9904374W WO0000031A1 WO 2000000031 A1 WO2000000031 A1 WO 2000000031A1 EP 9904374 W EP9904374 W EP 9904374W WO 0000031 A1 WO0000031 A1 WO 0000031A1
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- WIPO (PCT)
- Prior art keywords
- formula
- compound
- methine
- nitrogen
- ethyl
- Prior art date
Links
- 0 *Oc1c(-c2ccccc2)nnc(Cl)c1 Chemical compound *Oc1c(-c2ccccc2)nnc(Cl)c1 0.000 description 2
- KIEDNEWSYUYDSN-UHFFFAOYSA-N CC(C)(CON1Cc(cccc2)c2Cl)C1=O Chemical compound CC(C)(CON1Cc(cccc2)c2Cl)C1=O KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 description 1
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N CC(C)N(C(c1ccccc1N1)=O)S1(=O)=O Chemical compound CC(C)N(C(c1ccccc1N1)=O)S1(=O)=O ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 1
- MHULQDZDXMHODA-UHFFFAOYSA-N CC(CC1)(N(CC(C)(C)C2)C1=O)N2C(C(Cl)Cl)=O Chemical compound CC(CC1)(N(CC(C)(C)C2)C1=O)N2C(C(Cl)Cl)=O MHULQDZDXMHODA-UHFFFAOYSA-N 0.000 description 1
- RUUGSIXHWKTTFM-UHFFFAOYSA-N CCCN1c(cc(c(F)c2)N(C(C3=C4CCCC3)=O)C4=O)c2OCC1=O Chemical compound CCCN1c(cc(c(F)c2)N(C(C3=C4CCCC3)=O)C4=O)c2OCC1=O RUUGSIXHWKTTFM-UHFFFAOYSA-N 0.000 description 1
- MKQSWTQPLLCSOB-UHFFFAOYSA-N O=C(c([s]1)c(C(F)(F)F)nc1Cl)OCc1ccccc1 Chemical compound O=C(c([s]1)c(C(F)(F)F)nc1Cl)OCc1ccccc1 MKQSWTQPLLCSOB-UHFFFAOYSA-N 0.000 description 1
Classifications
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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
- A01N43/80—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
Definitions
- the present invention relates to a new herbicidal synergistic agent which contains a herbicidal active ingredient combination which is suitable for selective weed control in crops of useful plants, such as, for example, in crops of maize.
- the invention further relates to a method for controlling weeds in crops and the use of this new agent for this purpose.
- n 0 or 1 have herbicidal activity, as described, for example, in WO 97/43270.
- a new synergistic agent for selective weed control which, in addition to the usual inert formulation auxiliaries, comprises a mixture of a) a compound of the formula I as active ingredient
- n 0 or 1
- b a synergistically effective amount of one or more compounds selected from the compound of formula 2.1
- R 3 is ethyl, R 4 for methyl or ethyl and R 5 for -CH (Me) -CH 2 OMe, ⁇ S> -CH (Me) -CH 2 OMe. CH 2 OMe or CH 2 O-CH 2 CH 3 ; and the compound of formula 2.3
- R 10 is ethyl or n-propyl, Rn COO " 1/2 Ca ++ , -CH 2 -CH (Me) S-CH 2 CH 3 or the group
- R 12 is hydrogen, methoxy or ethoxy, R 13 Me, methoxy or fluorine, R M COOMe, fluorine or chlorine, R 15 hydrogen or Me, Y methine or nitrogen, Z methine or nitrogen and R 16 fluorine or chlorine; and the compound of formula 2.7
- R 17 is hydrogen or -C (O) -Sn-octyl; and the compound of formula 2.8
- R 18 is bromine or iodine; and the compound of formula 2.9
- R 20 is fluorine or chlorine and R 21 -CH 2 -CH (CI) -COOCH 2 CH 3 or -NH-SO 2 Me; and the compound of formula 2.11
- R 22 trifluoromethyl or chlorine; and the compound of formula 2.12 wherein R 23 is NH 2 or ⁇ S> NH 2 ; and the compound of formula 2.13
- Y nitrogen, methine or N-Me, Y 2 nitrogen, methine or Cl, Y 3 methine, Y 4 methine or Y 3 and Y 4 together sulfur or C-Cl, Y 5 nitrogen or methine, Y 6 for methyl or
- the combination of the active ingredient of the formula I with one or more active ingredients selected from the formulas 2 1 to 2 33 exceeds the additive action which is to be expected in principle on the weeds to be combated and thus limits the action of the individual active ingredients, in particular in expanded in two respects
- the application rates of the Emzel compounds of the formulas I and 2 1 to 2 33 are reduced with a consistently good effect This has resulted in a substantial broadening of the weed spectrum and an additional increase in the selectivity for the crops of crops, as is necessary and desirable in the event of an unintentional overdose of active ingredient.
- the agent according to the invention allows greater flexibility in subsequent crops while maintaining excellent control of the weeds in crop plants
- the agent according to the invention can be used against a large number of agronomically important weeds, such as Stella ⁇ a Nasturtium, Agrostis, Digitana, Avena, Setana, Sinapis, Lolium, Solanum, Phaseolus, Echinochloa, Scirpus, Monochona, Sagittana, Bromus, Alopecurus, Sorghum halepense, Rottusboellia , Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea Chrysanthemum, Gahum, Viola and Veronica can be used.
- the agent according to the invention is suitable for all application methods customary in agriculture such as pre-emergence application, post-emergence application and seed dressing.
- the agent according to the invention is suitable preferably for weed control in crops such as cereals, oilseed rape, sugar beet, sugar cane, plantations, rice, corn and soybeans and for non-selective weed control
- Cultures are also to be understood as those which have been made tolerant to herbicides or classes of herbicides by means of conventional breeding or genetic engineering methods
- the compound of the formula 2.9 in which R 19 is NO 2 , is known under the name mesotrione and is described, for example, in US Pat. No. 5,006,158.
- the compound of formula 2.21 and its preparation is described in US-A-5, 183,492, the compound of formula 2.22 is described under the name Isoxachlortole in AGROW No. 296, January 16, 1998, page 22.
- the compound of Formula 2.31 is called Fentrazamide in The 1997 British Crop Protection Conference - Weeds, Conference Proceedings Vol. 1, 2-8. Pages 67 to 72, the compound of formula 2.32 is described under the name JV 485 (isoxapropazole) in The 1997 British Crop Protection Conference - Weeds, Conference Proceedings Vol. 1, 3A-2, pages 93 to 98.
- Preferred synergistic mixtures according to the invention contain as active ingredients a compound of the formula I and either a compound of the formula 2.2.1 (2.2.1, aRS, 1'S (-) N- (1'-methyl-2'-methoxyethyl) -N-
- Another group of preferred synergistic mixtures according to the invention contain as active ingredients a compound of formula I, a compound of formula 2.2.1 (2.2.1, aRS, 1 'S (-) N- (1'methyl-2'-methoxyethyl) -N-
- R 7 is chlorine, R 8 is ethyl and R 9 isopropyl, or R 7 is chlorine, R 8 is ethyl and R 9 represents tert.-butyl, and of the formula 2.6, wherein R 12 is hydrogen, Z methine, R 13 is methyl, Y is nitrogen, R 14 is fluorine, R 15 is hydrogen, and R 16 is fluorine, or R 12 is methoxy, Z is methine, R 13 is Methoxy, Y methine, R 14 is chlorine, R 15 is methyl and R 16 is chlorine, and of the formula 2.7, in which R 17 is -C (O) -Sn-octyl, and of the formula 2.13, in which Y, nitrogen, Y 2 , Y 3 and Y 4 methine, R 24 dimethylaminocarbonyl and Y 5 methine, or Yi, Y
- the agent according to the invention contains the active ingredient of the formula I and the active ingredients of the formulas 2.1 to 2.33 in any mixing ratio, as a rule with an excess of one over the other component.
- the mixing ratios (weight ratios) between the active ingredient of the formula i and the mixing partners of the formulas 2.1 to 2.33 are between 1: 2000 to 2000: 1, in particular between 200: 1 and 1: 200.
- the application rate can vary within wide ranges and depends on the nature of the soil, the type of application (pre- or post-emergent; seed dressing; application in the seed furrow; no tillage application etc.), the crop, the weed to be controlled, the prevailing one climatic conditions and other factors determined by the type of application, time of application and target culture.
- the active substance mixture according to the invention can be applied at a rate of 1 to 5000 g of active substance mixture / ha.
- the mixtures of the compound of formula I with the compounds of formulas 2.1 to 2.33 can be used in unchanged form, i.e. as they arise in the synthesis. However, they are preferably processed in the customary manner with the auxiliaries customary in formulation technology, such as solvents, solid carriers or surfactants, e.g. to emulsifiable concentrates, directly sprayable or dilutable solutions, diluted emulsions, wettable powders, soluble powders, dusts, granules or microcapsules.
- the application methods such as spraying, atomizing, dusting, wetting, scattering or pouring, like the type of agent, are chosen in accordance with the intended goals and the prevailing conditions.
- formulations i.e. the agents, preparations or compositions containing the active compounds of the formulas I and 2.1 to 2.33 and, if appropriate, one or more solid or liquid formulation auxiliaries are prepared in a manner known per se, e.g. by intimately mixing and / or grinding the active ingredients with the formulation auxiliaries, e.g. Solvents or solid carriers.
- formulation auxiliaries e.g. Solvents or solid carriers.
- surface-active compounds surfactants
- surfactants can also be used in the preparation of the formulations.
- suitable surface-active compounds are nonionic, cationic and / or anionic surfactants and surfactant mixtures with good emulsifying, dispersing and wetting properties.
- suitable anionic, nonionic and cationic surfactants are listed, for example, in WO 97/34485. Pages 7 and 8.
- the herbicidal formulations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of active compound from the compound of the formula I with the compounds of the formulas 2.1 to 2.33, 1 to 99.9% by weight of a solid or liquid formulation auxiliary and 0 to 25% by weight, in particular 0.1 to 25% by weight, of a surfactant.
- agents While concentrated agents are usually preferred as commercial goods, the end user generally uses diluted agents.
- the agents can also contain other additives such as stabilizers e.g. optionally epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soybean oil), defoamers, e.g. Contain silicone oil, preservatives, viscosity regulators, binders, adhesives as well as fertilizers or other active ingredients.
- stabilizers e.g. optionally epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soybean oil), defoamers, e.g. Contain silicone oil, preservatives, viscosity regulators, binders, adhesives as well as fertilizers or other active ingredients.
- defoamers e.g. Contain silicone oil, preservatives, viscosity regulators, binders, adhesives as well as fertilizers or other active ingredients.
- Emulsifiable concentrates are:
- Active ingredient mixture 1 to 90%, preferably 5 to 20% surface-active agent: 1 to 30%, preferably 10 to 20% liquid carrier: 5 to 94%, preferably 70 to 85%
- Active ingredient mixture 0.1 to 10%, preferably 0.1 to 5% solid carrier: 99.9 to 90%, preferably 99.9 to 99%
- Active ingredient mixture 5 to 75%, preferably 10 to 50%
- Active ingredient mixture 0.5 to 90%, preferably 1 to 80% surface-active agent: 0.5 to 20%, preferably 1 to 15% solid carrier material: 5 to 95%, preferably 15 to 90%
- Active ingredient mixture 0.1 to 30%, preferably 0.1 to 15% solid carrier: 99.5 to 70%, preferably 97 to 85%
- Emulsion concentrates a) b) c) d)
- Active ingredient mixture 5% 10% 25% 50%
- Such concentrates can be used to prepare emulsions of any desired concentration by dilution with water.
- Active ingredient mixture 5% 10% 50% 90% 1-methoxy-3- (3-methoxy-propoxy) propane - 20% 20%
- the solutions are suitable for use in the form of tiny drops.
- Active ingredient mixture 5% 25% 50% 80%
- the active ingredient is mixed well with the additives and ground well in a suitable grinder.
- Spray powder is obtained which can be diluted with water to form suspensions of any desired concentration.
- Active ingredient mixture 0.1% 5% 15%
- the active ingredient is dissolved in methylene chloride, sprayed onto the carrier and that
- Active ingredient mixture 0.1% 5% 15%
- the finely ground active ingredient is evenly applied in a mixer to the carrier material moistened with polyethylene glycol. In this way, dust-free coating granules are obtained.
- Active ingredient mixture 0.1% 3% 5% 15%
- the active ingredient is mixed with the additives, ground and moistened with water. This mixture is extruded and then dried in an air stream.
- Active ingredient mixture 0.1% 1% 5%
- Ready-to-use dusts are obtained by mixing the active ingredient with the carrier substances and grinding them in a suitable mill.
- the finely ground active ingredient is intimately mixed with the additives. This gives a suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water.
- a synergistic effect is always present when the effect of the active ingredient combination of the compound of the formula I with the compounds of the formulas 2.1 to 2.33 is greater than the sum of the effect of the individually applied active ingredients.
- Y percent herbicidal activity when treated with a compound of the formulas 2.1 to 2.33 with q kg application rate per hectare compared to the untreated control.
- We expected herbicidal activity (percent herbicidal activity compared to the untreated control) after treatment with the compounds of the formulas I and 2.1 to 2.33 at an application rate of p + q kg of active ingredient per hectare. If the actually observed effect is greater than the expected value We, there is synergism.
- test plants are grown under greenhouse conditions in plastic pots up to the 2-3 leaf stage.
- a standard earth is used as a growing medium.
- the herbicides are applied alone or as a mixture to the test plants.
- Application takes place as an aqueous suspension of the test substances in 500 l of water / ha.
- the application rates depend on the optimal dosages determined under field conditions and greenhouse conditions.
- the compound of the formula I in which n is 0 is referred to as the compound of the formula Ia.
- the compound of the formula I in which n is 1 is referred to as the compound of the formula Ib.
- the present invention therefore also relates to a selective herbicidal composition for controlling grasses and weeds in crops of useful plants, in particular in crops of maize, which is a compound of the formula I, optionally one or more compounds selected from the compounds of the formulas 2.1 to 2.33 and contains a safener (antidote, antidote) and which protects the useful plants but not the weeds from the phytotoxic effect of the herbicide, and the use of this agent for weed control in useful plant crops.
- a safener antidote, antidote
- a selective herbicidal agent which is characterized in that, in addition to the usual inert formulation auxiliaries such as carriers, solvents and wetting agents, it is a mixture of active ingredients a) a herbicidally synergistically effective amount of a compound of the formula I and one or more compounds selected from the compounds of the formulas 2.1 to 2.33 and b) a herbicidally antagonistically effective amount of a compound selected from the compound of the formula 3.1
- a particularly preferred selective herbicidal composition contains a) a herbicide-synergistically effective amount of a compound of the formula I and a compound of the formula 2.2.1
- those selective herbicidal compositions according to the invention which contain a compound of the formula I, a compound of the formula 2.2 as herbicide-synergistically effective amount and a compound selected from the compounds of the formulas 3.1 to 3.1 1 as a herbicide-antagonistically effective amount.
- the invention further relates to a selective herbicidal composition which is characterized in that, in addition to customary inert formulation auxiliaries such as carriers, solvents and wetting agents, as active ingredient a mixture of a) a herbicidally active amount of a compound of the formula I and b) a herbicidal antagonistically effective amount of a compound selected from the compound of formula 3.1
- the invention further relates to a method for the selective control of weeds in crops, which consists in that the crops, their seeds or cuttings or their cropland with a herbicidally effective amount of the herbicide of the formula I, optionally one or more herbicides selected from the Compounds of the formulas 2.1 to 2.33 and a herbicide-antagonistically effective amount of a safener of the formulas 3.1 to 3.11 treated.
- the compounds of the formulas 3.1 to 3.1 1 are known and, for example, in the Pesticide Manual, eleventh ed., British Crop Protection Council, 1997 under entry numbers 61 (Formula 3.1, Benoxacor). 304 (Formula 3.2, Fenclorim), 154 (Formula 3.3, Cloquintocet), 462 (Formula 3.4, Mefenpyr-diethyl), 377 (Formula 3.5, Furilazole), 363 (Formula 3.8, Fluxofenim), 213 (Formula 3.9, Dichlormid) and 350 (Formula 3.10, Flurazole).
- the compound of formula 3.1 1 is known under the name MON 4660 (Monsanto).
- the compound of formula 3.6 (AC 304415) is described for example in EP-A-0 613 618, the compound of formula 3.7 in DE-A-2948535.
- Crops which can be protected by the safeners of the formulas 3.1 to 3.1 1 against the harmful action of the herbicides mentioned above include, in particular, cereals, cotton, soybeans, sugar beets, sugar cane, plantations, rapeseed, maize and rice, particularly in maize Consideration. Cultures are also to be understood as those which have been made tolerant to herbicides or classes of herbicides by means of conventional breeding or genetic engineering methods.
- the weeds to be controlled can be both monocot and dicot weeds, such as Stellaria, Agrostis, Digitaria, Avena, Apera, Brachiaria, Phalaris, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Panicum, Bromus, Alopecurus, Sorghum halepense, Sorghum bicolor, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica.
- Stellaria Agrostis, Digitaria, Avena, Apera, Brachiaria, Phalaris, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Panicum, Bromus, Alopecurus, Sorghum hale
- the cultivated areas are the soil areas already overgrown with the crop plants or filled with the seeds of these crop plants, as well as the soils intended for cultivation with these crop plants.
- a safener of the formula 3.1 to 3.11 can be used for the pretreatment of the seed of the crop (dressing the seed or the cuttings) or added to the soil before or after the seed. But he can also do it alone or applied together with the herbicide after emergence of the plants.
- the treatment of the plants or the seed with the safener can therefore in principle be carried out independently of the time of application of the herbicide. However, the treatment of the plant can also be carried out by simultaneous application of herbicide and safener (for example as a tank mix).
- the application rate of safener to herbicide largely depends on the type of application.
- the ratio of herbicides to safener is generally from 100: 1 to 1:10, preferably 20: 1 to 1: 1, before.
- 0.001 to 1.0 kg safener / ha preferably 0.001 to 0.25 kg safener / ha, are applied in the field treatment.
- the application rates of herbicides are generally between 0.001 to 2 kg / ha, but preferably between 0.005 to 0.5 kg / ha.
- the agents according to the invention are suitable for all application methods customary in agriculture, e.g. preemergent application, postemergent application and seed dressing suitable.
- safener solutions which contain the active compound in a concentration of 1 to 10,000, preferably 100 to 1000 ppm.
- the safeners of the formulas 3.1 to 3.1 1 or combinations of these safeners with the herbicide of the formula I and one or more herbicides selected from the formulas 2.1 to 2.33 are expediently processed together with the auxiliaries customary in formulation technology, for example to form emulsion concentrates , spreadable pastes, directly sprayable or dilutable solutions, diluted emulsions, wettable powders, soluble powders, dusts, granules or microcapsules.
- auxiliaries customary in formulation technology for example to form emulsion concentrates , spreadable pastes, directly sprayable or dilutable solutions, diluted emulsions, wettable powders, soluble powders, dusts, granules or microcapsules.
- Such formulations are described for example in WO 97/34485 on pages 9 to 13.
- the formulations are prepared in a known manner, for example by intimately mixing and / or grinding the active ingredients with liquid or solid formulation auxiliaries, such as, for example, solvents or solid carriers.
- liquid or solid formulation auxiliaries such as, for example, solvents or solid carriers.
- surface-active compounds surfactants
- Suitable solvents and solid carriers for this purpose are given, for example, on page 6 in WO 97/34485.
- formulas I, 2.1 to 2.33 and 3.1 to 3.1, 1 1 non-ionic, cationic and / or anionic surfactants and surfactant mixtures with good emulsifying, dispersing and wetting properties are suitable as surface-active compounds.
- suitable anionic, nonionic and cationic surfactants are listed, for example, in WO 97/34485 on pages 7 and 8.
- the surfactants commonly used in formulation technology which include in "Mc Cutcheon's Detergents and Emulsifiers Annual” MC Publishing Corp., Ridgewood New Jersey, 1981, Stumbleen, H., "Tensid-Taschenbuch", Carl Hanser Verlag, Kunststoff / Vienna, 1981 and M. and J. Ash, "Encyclopedia of Surfactants ", Vol III, Chemical Publishing Co., New York, 1980-81, are suitable for the preparation of the herbicidal compositions according to the invention.
- the herbicidal formulations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of active compound from the compound of the formula I, a compound selected from the compounds of the formulas 2.1 to 2.33 and the compounds of the formulas 3.1 to 3.1 1, 1 to 99.9% by weight of a solid or liquid formulation auxiliary and 0 to 25% by weight, in particular 0.1 to 25% by weight of a surfactant. While concentrated agents are usually preferred as commercial goods, the end user generally uses diluted agents.
- the agents can also contain further additives such as stabilizers, for example epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soybean oil), defoamers, for example silicone oil, preservatives, viscosity regulators, binders, adhesives and fertilizers or other active ingredients.
- stabilizers for example epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soybean oil)
- defoamers for example silicone oil
- preservatives for example silicone oil
- viscosity regulators binders
- adhesives and fertilizers or other active ingredients e.g., adhesives and fertilizers or other active ingredients.
- Seed dressing a) Dressing the seeds with an active ingredient of the formulas 3.1 to 3.11 formulated as a wettable powder by shaking in a vessel until uniformly distributed on the seed surface (dry dressing). About 1 to 500 g of active ingredient of the formulas 3.1 to 3.1 1 (4 g to 2 kg of wettable powder) are used per 100 kg of seed. b) dressing the seeds with an emulsion concentrate of the active ingredient of the formulas 3.1 to 3.1 1 according to method a) (wet dressing). c) Dressing by immersing the seed in a broth with 100-1000 ppm of active ingredient of the formulas 3.1 to 3.1 1 for 1 to 72 hours and, if appropriate, subsequently drying the seeds (immersion dressing).
- the dressing of the seeds or the treatment of the germinated seedlings are naturally the preferred methods of application because the treatment of the active ingredient is completely aimed at the target culture.
- 1 to 1000 g antidote, preferably 5 to 250 g antidote, are used per 100 kg of seed, depending on the method, which also allows the addition of other active substances or micronutrients, to deviate upwards or downwards from the specified limit concentrations ( Repeat stain).
- a liquid processing of a mixture of antidote and herbicide (mutual ratio between 10: 1 and 1: 100) is used, the amount of herbicide applied being 0.005 to 5.0 kg per hectare.
- Such tank mixes are applied before or after sowing.
- the active ingredients of the formulas 3.1 to 3.1 1 are introduced into the open seeded furrow as emulsion concentrate, wettable powder or as granules. After covering the seed furrow, the herbicide is applied in the pre-emergence process in the usual way.
- Emulsifiable concentrates are:
- Active ingredient mixture 1 to 90%, preferably 5 to 20% surface-active agent: 1 to 30%, preferably 10 to 20% liquid carrier: 5 to 94%, preferably 70 to 85%
- Active substance mixture 0.1 to 10%, preferably 0.1 to 5% solid carrier: 99.9 to 90%, preferably 99.9 to 99 °
- Active ingredient mixture 5 to 75%, preferably 10 to 50%
- Wettable powders active ingredient mixture: 0.5 to 90%, preferably 1 to 80% surface-active agent: 0.5 to 20%, preferably 1 to 15% solid carrier material: 5 to 95%, preferably 15 to 90%
- Active ingredient mixture 0.1 to 30%, preferably 0.1 to 15% solid carrier: 99.5 to 70%, preferably 97 to 85%
- Active substance mixture 5% 10% 25% 50%
- Such concentrates can be used to prepare emulsions of any desired concentration by dilution with water.
- Active ingredient mixture 5% 10% 50% 90%
- the solutions are suitable for use in the form of tiny drops.
- Active ingredient mixture 5% 25% 50% 80%
- the active ingredient is mixed well with the additives and ground well in a suitable grinder.
- Spray powder is obtained which can be diluted with water to form suspensions of any desired concentration.
- Active ingredient mixture 0.1% 5% 15%
- the active ingredient is dissolved in methylene chloride, sprayed onto the carrier and that
- Active ingredient mixture 0.1% 5% 15%
- Polyethylene glycol MG 200 1 .0% 2% 3%
- the finely ground active ingredient is evenly applied in a mixer to the carrier material moistened with polyethylene glycol. In this way, dust-free coating granules are obtained.
- Active ingredient mixture 0.1% 3% 5% 15%
- the active ingredient is mixed with the additives, ground and moistened with water. This mixture is extruded and then dried in an air stream.
- Ready-to-use dusts are obtained by mixing the active ingredient with the carrier substances and grinding them in a suitable mill.
- Active ingredient mixture 3% 10% 25% 50%
- the finely ground active ingredient is intimately mixed with the additives. This gives a suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water.
- test plants are grown in plastic pots up to the 4-leaf stage under greenhouse conditions. At this stage, the herbicides alone and the mixtures of the herbicides with the test substances to be tested as safeners are applied to the test plants. The application takes place as an aqueous suspension of Test substances, made from a 25% wettable powder (example F3, b)), with 500 l of water / ha. 3 weeks after application, the phytotoxic effect of the herbicides on the crop plants, such as corn and cereals, is evaluated using a percentage scale. 100% means test plant has died, 0% means no phytotoxic effect.
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
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Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP99931160A EP1089628A1 (de) | 1998-06-26 | 1999-06-24 | Herbizides mittel |
AU47768/99A AU4776899A (en) | 1998-06-26 | 1999-06-24 | Herbicide |
US09/748,347 US20010044382A1 (en) | 1998-06-26 | 2000-12-26 | Herbicide |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH137398 | 1998-06-26 | ||
CH1373/98 | 1998-06-26 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/748,347 Continuation US20010044382A1 (en) | 1998-06-26 | 2000-12-26 | Herbicide |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000000031A1 true WO2000000031A1 (de) | 2000-01-06 |
Family
ID=4208910
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1999/004374 WO2000000031A1 (de) | 1998-06-26 | 1999-06-24 | Herbizides mittel |
Country Status (4)
Country | Link |
---|---|
US (1) | US20010044382A1 (de) |
EP (1) | EP1089628A1 (de) |
AU (1) | AU4776899A (de) |
WO (1) | WO2000000031A1 (de) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000030447A1 (de) * | 1998-11-21 | 2000-06-02 | Aventis Cropscience Gmbh | Kombinationen aus herbiziden und safenern |
GB2350298A (en) * | 1999-05-28 | 2000-11-29 | Zeneca Ltd | The safening of 2-benzoylcyclohexane-1,3-dione herbicides with 1-phenyl-1,2,4-triazole, 1-phenyl-pyrazolin-3-carboxylate & 8-oxy-quinoline derivatives |
WO2000074488A1 (en) * | 1999-06-04 | 2000-12-14 | Aventis Agriculture Ltd. | Method of controlling weeds in transgenic crops |
WO2001017350A1 (en) * | 1999-09-08 | 2001-03-15 | Aventis Cropscience Uk Limited | New herbicidal compositions |
WO2001028341A2 (de) * | 1999-10-22 | 2001-04-26 | Aventis Cropscience Gmbh | Hydroxyphenylpyruvat-dioxygenaseinhibitor-herbizide in synergistischen mischungen |
WO2001054501A2 (en) * | 2000-01-25 | 2001-08-02 | Syngenta Participations Ag | Herbicidal composition |
EP1161868A1 (de) * | 2000-06-07 | 2001-12-12 | Aventis Cropscience S.A. | Herbizide Zusammensetzungen |
WO2002063957A2 (de) * | 2001-02-12 | 2002-08-22 | Bayer Cropscience Ag | Selektive herbizide auf basis von substituierten arylketonen und safenern |
WO2002071845A1 (de) * | 2001-03-14 | 2002-09-19 | Bayer Cropscience Ag | Herbizide auf basis von substituierten arylketonen |
WO2002087322A3 (en) * | 2001-04-27 | 2002-12-19 | Syngenta Participations Ag | Herbicidal composition |
WO2003022050A1 (de) * | 2001-09-13 | 2003-03-20 | Bayer Cropscience Gmbh | Kombinationen aus herbiziden und safenern |
WO2005104848A1 (en) * | 2004-04-30 | 2005-11-10 | Syngenta Participations Ag | Herbicidal composition |
WO2019166399A1 (en) * | 2018-02-28 | 2019-09-06 | Bayer Aktiengesellschaft | Method of reducing crop damage |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19836659A1 (de) * | 1998-08-13 | 2000-02-17 | Hoechst Schering Agrevo Gmbh | Herbizide Mittel für tolerante oder resistente Baumwollkulturen |
JP4839558B2 (ja) * | 2001-09-26 | 2011-12-21 | 住友化学株式会社 | 顆粒状水和剤 |
ES2333977T3 (es) * | 2004-10-05 | 2010-03-03 | Syngenta Limited | Derivados de isoxazolina y su uso como herbicidas. |
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WO1997022253A1 (en) * | 1995-12-20 | 1997-06-26 | Rhone-Poulenc Agriculture Limited | Herbicidal compositions containing 4-benzoylisoxazoles and a hydroxybenzonitrile |
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WO1999021842A1 (en) * | 1997-10-28 | 1999-05-06 | Zeneca Limited | Herbicidal 4-benzoylisoxazoles derivatives |
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1999
- 1999-06-24 EP EP99931160A patent/EP1089628A1/de not_active Withdrawn
- 1999-06-24 WO PCT/EP1999/004374 patent/WO2000000031A1/de not_active Application Discontinuation
- 1999-06-24 AU AU47768/99A patent/AU4776899A/en not_active Abandoned
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2000
- 2000-12-26 US US09/748,347 patent/US20010044382A1/en not_active Abandoned
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WO1997022253A1 (en) * | 1995-12-20 | 1997-06-26 | Rhone-Poulenc Agriculture Limited | Herbicidal compositions containing 4-benzoylisoxazoles and a hydroxybenzonitrile |
WO1997043270A1 (en) * | 1996-05-14 | 1997-11-20 | Novartis Ag | Isoxazole derivatives and their use as herbicides |
WO1999021842A1 (en) * | 1997-10-28 | 1999-05-06 | Zeneca Limited | Herbicidal 4-benzoylisoxazoles derivatives |
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WO2000030447A1 (de) * | 1998-11-21 | 2000-06-02 | Aventis Cropscience Gmbh | Kombinationen aus herbiziden und safenern |
GB2350298A (en) * | 1999-05-28 | 2000-11-29 | Zeneca Ltd | The safening of 2-benzoylcyclohexane-1,3-dione herbicides with 1-phenyl-1,2,4-triazole, 1-phenyl-pyrazolin-3-carboxylate & 8-oxy-quinoline derivatives |
WO2000074488A1 (en) * | 1999-06-04 | 2000-12-14 | Aventis Agriculture Ltd. | Method of controlling weeds in transgenic crops |
WO2001017350A1 (en) * | 1999-09-08 | 2001-03-15 | Aventis Cropscience Uk Limited | New herbicidal compositions |
US8642509B2 (en) | 1999-09-08 | 2014-02-04 | Aventis Cropscience Uk Limited | Herbicidal compositions |
HRP20020207B1 (en) * | 1999-09-08 | 2011-06-30 | Aventis Cropscience Uk Limited | New herbicidal compositions |
US20060240984A1 (en) * | 1999-09-08 | 2006-10-26 | Ken Pallett | Herbicidal compositions |
US7056863B1 (en) | 1999-10-22 | 2006-06-06 | Aventis Cropscience Gmbh | Synergistic herbicidal compositions herbicides from the group of the hydroxyphenylpyruvate dioxygenase inhibitors |
WO2001028341A2 (de) * | 1999-10-22 | 2001-04-26 | Aventis Cropscience Gmbh | Hydroxyphenylpyruvat-dioxygenaseinhibitor-herbizide in synergistischen mischungen |
WO2001028341A3 (de) * | 1999-10-22 | 2002-05-02 | Aventis Cropscience Gmbh | Hydroxyphenylpyruvat-dioxygenaseinhibitor-herbizide in synergistischen mischungen |
JP4880161B2 (ja) * | 2000-01-25 | 2012-02-22 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | 除草製剤 |
HRP20020669B1 (en) * | 2000-01-25 | 2011-07-31 | Syngenta Participations Ag | Herbicidal composition |
JP2003520861A (ja) * | 2000-01-25 | 2003-07-08 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | 除草製剤 |
CZ304537B6 (cs) * | 2000-01-25 | 2014-06-25 | Syngenta Participations Ag | Herbicidně selektivní kompozice a způsob kontroly nežádoucího rostlinného růstu |
WO2001054501A2 (en) * | 2000-01-25 | 2001-08-02 | Syngenta Participations Ag | Herbicidal composition |
WO2001054501A3 (en) * | 2000-01-25 | 2002-01-03 | Syngenta Participations Ag | Herbicidal composition |
EP1161868A1 (de) * | 2000-06-07 | 2001-12-12 | Aventis Cropscience S.A. | Herbizide Zusammensetzungen |
WO2002063957A2 (de) * | 2001-02-12 | 2002-08-22 | Bayer Cropscience Ag | Selektive herbizide auf basis von substituierten arylketonen und safenern |
WO2002063957A3 (de) * | 2001-02-12 | 2002-12-19 | Bayer Ag | Selektive herbizide auf basis von substituierten arylketonen und safenern |
WO2002071845A1 (de) * | 2001-03-14 | 2002-09-19 | Bayer Cropscience Ag | Herbizide auf basis von substituierten arylketonen |
US7196038B1 (en) | 2001-04-27 | 2007-03-27 | Syngenta Crop Protection, Inc. | Herbicidal composition |
WO2002087322A3 (en) * | 2001-04-27 | 2002-12-19 | Syngenta Participations Ag | Herbicidal composition |
HRP20040246B1 (en) * | 2001-09-13 | 2012-09-30 | Bayer Cropscience Ag | Herbicide and safening combinations |
CN1309302C (zh) * | 2001-09-13 | 2007-04-11 | 拜尔作物科学有限公司 | 除草剂与安全剂组合物 |
WO2003022050A1 (de) * | 2001-09-13 | 2003-03-20 | Bayer Cropscience Gmbh | Kombinationen aus herbiziden und safenern |
US6914035B2 (en) | 2001-09-13 | 2005-07-05 | Bayer Cropscience Gmbh | Combinations of herbicides and safeners |
AU2005237241B2 (en) * | 2004-04-30 | 2011-04-07 | Syngenta Limited | Herbicidal composition |
US8404618B2 (en) | 2004-04-30 | 2013-03-26 | Syngenta Limited | Herbicidal composition |
WO2005104848A1 (en) * | 2004-04-30 | 2005-11-10 | Syngenta Participations Ag | Herbicidal composition |
WO2019166399A1 (en) * | 2018-02-28 | 2019-09-06 | Bayer Aktiengesellschaft | Method of reducing crop damage |
CN111770684A (zh) * | 2018-02-28 | 2020-10-13 | 拜耳公司 | 减少作物损害的方法 |
US11219209B2 (en) | 2018-02-28 | 2022-01-11 | Bayer Aktiengesellschaft | Method of reducing crop damage |
Also Published As
Publication number | Publication date |
---|---|
EP1089628A1 (de) | 2001-04-11 |
AU4776899A (en) | 2000-01-17 |
US20010044382A1 (en) | 2001-11-22 |
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