EP2369931A2 - Association d'herbicides et de phytoprotecteurs - Google Patents

Association d'herbicides et de phytoprotecteurs

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Publication number
EP2369931A2
EP2369931A2 EP09756270A EP09756270A EP2369931A2 EP 2369931 A2 EP2369931 A2 EP 2369931A2 EP 09756270 A EP09756270 A EP 09756270A EP 09756270 A EP09756270 A EP 09756270A EP 2369931 A2 EP2369931 A2 EP 2369931A2
Authority
EP
European Patent Office
Prior art keywords
amino
chloro
cyclopropyl
pyrimidinecarboxylate
compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP09756270A
Other languages
German (de)
English (en)
Inventor
Christopher Hugh Rosinger
Erwin Hacker
Hartmut Ahrens
Hansjörg Dietrich
Frank Ziemer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Intellectual Property GmbH
Original Assignee
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Priority to EP09756270A priority Critical patent/EP2369931A2/fr
Publication of EP2369931A2 publication Critical patent/EP2369931A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

Definitions

  • the present invention relates to agrochemically active herbicide-safener combinations, to processes for their preparation and to their use for controlling harmful plants.
  • pyrimidine derivatives have herbicidal properties.
  • WO 2005/063721 A, WO 2007/082076 A and US 2007 0197391 describe pyrimidine derivatives which combat a broad spectrum of weeds.
  • some of these agents are not fully compatible with some important crops such as e.g. different cereals, corn or rice. Therefore, they can not be used in some crops to ensure the desired broad herbicidal activity against harmful plants.
  • EP-A 0 912 089, EP-A 1 019 368 and US 2007 0010399 describe safeners from the group of the acylsulfonamides or mixtures of these safeners with a wide variety of herbicides, but no herbicides of the formula (I) are disclosed as mixing partners.
  • WO 2007/120706 A describes mixtures of the pyrimidine derivatives of the formula (I) and certain safeners. By combining with safeners, the compatibility with crops should be increased. However, the compatibility of these mixtures is not satisfactory in some crops.
  • the subject of the present invention is therefore a composition containing
  • R 1 is cyclopropyl, 4-Br-phenyl or 4-CI-phenyl; X is chlorine or bromine; and R 2 represents hydrogen, Ci-Ci4-alkyl, C 2 -Ci4-alkoxyalkyl, C 3 -C 4 -
  • Alkoxyalkoxyalkyl C 2 -C 4 -hydroxyalkyl or benzyl
  • the herbicide-safener combinations according to the invention may contain additional other components, for example crop protection agents of another type and / or additives customary in plant protection and / or formulation auxiliaries, or be used together with them.
  • the herbicides (A) and the safeners (B) can be applied in a known manner, for example jointly (for example as a co-formulation or as a tank mixture) or also with a time offset (splitting), for example on the plants, plant parts, plant seeds or Surface on which the plants grow. It is possible, for example, the application of the individual active ingredients or herbicide-safener combination in several portions (sequence application), z. For applications pre-emergence, followed by post-emergence applications or early post-emergence applications, followed by mid-late post-emergence applications. Preference is given to the common or timely use of the active ingredients of the respective combination. It is also possible to use the individual active substances or the herbicide-safener combination for seed treatment.
  • the abovementioned formula (I) comprises all stereoisomers and mixtures thereof, in particular also racemic mixtures, and - as far as enantiomers are possible - both enantiomers and in particular the respective biologically active enantiomer.
  • Preferred herbicides (A) are compounds of the formula (I) and salts thereof, in which the radical
  • R 2 is hydrogen; C 1 -C 8 -alkyl; C 2 -C 8 alkoxyalkyl; C 3 -C 8 alkoxyalkoxyalkyl, or C 2 -C 8 hydroxyalkyl.
  • herbicides (A) are compounds of the formula (I) and salts thereof, in which the radical
  • R 2 is hydrogen or C 1 -C 2 -alkyl
  • herbicide (A) are compounds of the formula (I) and salts thereof, in which the radical
  • R 2 is C 5 -C 8 -alkyl, C 5 -C 8 -alkoxyalkyl, C 5 -C 8 -alkoxyalkoxyalkyl or C 5 -C 8 -hydroxyalkyl stands.
  • herbicides (A) are compounds of the formula (I) and their salts, which are selected from the group consisting of
  • the herbicide of the general formula (I) is selected from the group of the following compounds (1-1) to (I-3), (1-109), (1-163) and (1-164):
  • herbicide (A) more preferable are compounds of the formula (I) and their salts which are selected from the group consisting of
  • the compounds of formula (I) may further form salts by addition of a suitable inorganic or organic acid such as HCl, HBr, H 2 SO 4 or HNO 3 , but also oxalic acid or sulfonic acids to a basic group such as amino.
  • a suitable substituents which are present in deprotonated form, such as carboxylic acids, internal salts can in turn be protonatable groups as amino groups form. Salts can also be formed by replacing the hydrogen with a suitable cation for agriculture with suitable substituents, such as carboxylic acids.
  • salts are, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts with cations of the formula [NRR 1 R 11 R 1 "] * , where R to R "1 each independently represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl.
  • the compounds of the general formula (I) may also comprise N-oxides.
  • Corresponding pyridine-N-oxides are accessible via oxidation of the corresponding pyridines. Suitable oxidation methods are, for example, in Houben-Weyl, Methods of Organic Chemistry, Extension and follow-up volumes to the 4th edition, Volume E 7b, p 565 f. described.
  • radicals alkyl, alkoxyalkyl, hydroxyalkyl and alkoxyalkoxyalkyl can each be straight-chain or branched.
  • alkyl is understood to mean in particular the radicals methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, or the various isomers of pentyl or hexyl ,
  • alkoxyalkyl is understood to mean alkyl having an alkoxy substituent.
  • examples of the radical “alkoxyalkyl” include CH 3 OCH 2 , CH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 2 , CH 3 CH 2 CH 2 CH 2 OCH 2 , CH 3 CH 2 OCH 2 CH 2 , CH 3 CH 2 CH 2 CH 2 OCH 2 CH 2 or CH 3 CH 2 CH 2 CH 2 OCH 2 CHMe.
  • alkoxyalkoxy is understood as meaning alkoxy provided with an alkoxy substituent.
  • alkoxyalkoxyalkyl is understood as meaning a radical in which an alkoxyalkoxy substituent is attached to an alkyl radical.
  • alkoxyalkoxyalkyl include CH 3 OCH 2 OCH 21 CH 3 OCH 2 OCH 2 CH 21 CH 3 CH 2 OCH 3 OCH 2 and CH 3 OCH 3 CH 2 OCH 2 CH 2 .
  • hydroxyalkyl is understood to mean alkyl having a hydroxy substituent.
  • examples of “hydroxyalkyl” include HOCH 2 CH 2 , HOCH 2 CH 2 CH 2 and HOCH 2 CH 2 CH 2 CH 2 .
  • radicals with carbon atoms those having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, are generally preferred.
  • the present invention also provides mixtures comprising stereoisomers which are encompassed by formula (I) or by the formulas of component B (safener).
  • Such compounds of the formula (I) or of the formulas of the component B (safener) contain, for example, one or more asymmetrically substituted carbon atoms or sulfoxides.
  • the possible stereoisomers defined by their specific spatial form, such as enantiomers and diastereomers, are all encompassed by the formula (I) or by the formulas of component B (safener) and can be obtained by conventional methods from mixtures of stereoisomers or also by stereoselective reactions in combination be prepared with the use of stereochemically pure starting or auxiliary materials.
  • the application rates are generally lower, z.
  • 0.1 g to 800 g a.i./ha preferably 1 g to 500 g a.i./ha, more preferably 10 g to 400 g a.i./ha.
  • the herbicides of general formula (I) (A) are for combating
  • Harmful plants e.g. suitable in crops, for example in economically important crops e.g. monocotyledonous crops such as cereals (e.g., wheat, barley, rye, oats), rice, corn, millet, or dicotyledonous crops such as sugar beet, oilseed rape, cotton, sunflower and legumes, e.g. of the genera Glycine (eg Glycine max. (soy) as non-transgenic Glycine max.
  • monocotyledonous crops such as cereals (e.g., wheat, barley, rye, oats), rice, corn, millet, or dicotyledonous crops such as sugar beet, oilseed rape, cotton, sunflower and legumes, e.g. of the genera Glycine (eg Glycine max. (soy) as non-transgenic Glycine max.
  • Phaseolus eg conventional varieties such as STS strains
  • transgenic Glycine max eg RR soy or LL soy
  • Phaseolus Phaseolus
  • Pisum Phaseolus
  • Vicia and Arachis or vegetable crops from various botanical groups such as potato, leek, cabbage, carrot, tomato, onion, and permanent and plantation crops such as pome and stone fruit, soft fruit, wine, Hevea, bananas, sugar cane, coffee, tea, citrus , Nut orchards, lawns, palm tree crops and forest crops.
  • these cultures are also preferred, the use in cereals (eg wheat, barley, rye, oats), rice, corn, millet, sugar beet, sugar cane is particularly preferred , Sunflower, rapeseed and cotton.
  • cereals eg wheat, barley, rye, oats
  • rice, corn, millet, sugar beet, sugar cane is particularly preferred
  • Sunflower, rapeseed and cotton are particularly preferred.
  • Herbicide-safener combinations (A) + (B) are also useful in tolerant and non-tolerant mutant cultures and tolerant and non-tolerant transgenics Cultures, preferably corn, rice, cereals, oilseed rape and soy, for example those which are resistant to imidazolinone herbicides, atrazine, glufosinate or glyphosate.
  • the compounds of the general formula (I) are known from WO 2007/120706 A1 and can be obtained by the processes described therein.
  • the safeners contained as component (B) are understood to be compounds which are suitable for the phytotoxic effects of
  • Crop protection agents such as herbicides to reduce crops.
  • the safener compounds are selected from the following groups:
  • S1a Derivatives of dichlorophenylpyrazole monocarboxylic acid (S1a), preferably compounds such as ethyl 1- (2,4-dichlorophenyl) -5-methylpyrazole-3-carboxylate
  • S1b) derivatives of 1,5-diphenylpyrazole-3-carboxylic acid S1b
  • S1b preferably compounds such as 1- (2,4-dichlorophenyl) -5-phenylpyrazole-3-carboxylic acid ethyl ester (S-4), 1- (2- Chlorophenyl) -5-phenylpyrazole-3-carboxylic acid methyl ester (S-5) and related compounds as described, for example, in EP-A-268554;
  • S2a compounds of the (5-chloro-8-quinolinoxy) malonic acid (S2a) type, preferably compounds such as diethyl (5-chloro-8-quinolinoxy) malonate (S-6), (5-chloro-8-quinolinoxy) malonic acid ( S-7), (5-chloro-8-quinolinoxy) malonic acid methyl ethyl ester (S-8) and related
  • Pre-emergence safeners can be applied: "R-29148” (3-dichloroacetyl-2,2,5-trimethyl-1, 3-oxazolidine) from Stauffer
  • PPG-1292 N-allyl-N - [(1, 3-dioxolan-2-yl) -methyl] -dichloroacetamide
  • AD-67 or "MON 4660” (3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decane) of
  • RA 2 is halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy, CF 3 ; mA 1 or 2; vA is 0, 1, 2 or 3;
  • RB 1 , RB 2 independently of one another hydrogen, (C 1 -C 6 -alkyl, (C 3 -Ce) -
  • RB 3 is halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl or (C 1 -C 4 ) -alkoxy and mB is 1 or 2,
  • R 8 1 isopropyl
  • R 8 2 hydrogen
  • (R 8 3 ) 5-CI-2-OMe is (S-19) and
  • R 8 1 isopropyl
  • R 8 2 hydrogen
  • (R 8 3 ) 2-OMe is (S-20).
  • Rc 1, Rc 2 are independently hydrogen, (C 1 -Ce) -alkyl, (C 3 -C 8) - cycloalkyl, (C 3 -C 6) -alkenyl, (C 3 -C 6) alkynyl,
  • R c 3 is halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy, CF 3 mC is 1 or 2;
  • S7 compounds from the class of the diphenylmethoxyacetic acid derivatives (S7), eg methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S-35), ethyl diphenylmethoxyacetate (S-36) or diphenylmethoxyacetic acid (S-37) as described in WO 98/38856.
  • S7 diphenylmethoxyacetic acid derivatives
  • S-35 eg methyl diphenylmethoxyacetate
  • S-36 ethyl diphenylmethoxyacetate
  • S-37 diphenylmethoxyacetic acid
  • R 0 1 is halogen, (C r C4) alkyl, (dC 4) -haloalkyl, (Ci-C 4) alkoxy, (Ci-C 4) -
  • R 0 2 is hydrogen or (C 1 -C 4 ) -alkyl
  • R 0 3 is hydrogen, (C 1 -C 8 ) -alkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -alkynyl, or aryl, where each of the aforementioned C-containing radicals unsubstituted or by a or more, preferably up to three, identical or different radicals from the group consisting of halogen and alkoxy substituted; or their salts nD is 0, 1 or 2.
  • RE 1 is halogen, (C 1 -C 4 ) -alkyl, methoxy, nitro, cyano, CF 3 , OCF 3
  • nE is an integer of 0 to 4, RE 2 (CRCI 6) alkyl, (C 2 -C 6) alkenyl, (C 3 -C 6) -cycloalkyl, aryl; benzyl,
  • RE 3 is hydrogen or (Ci-C 6 ) alkyl.
  • Preferred herbicide-safener combinations comprising (A) a herbicidally effective amount of one or more compounds of formula (I) or their salts, and (B) an antidote effective amount of one or more safeners.
  • herbicidally effective amount means an amount of one or more herbicides which is suitable for negatively influencing plant growth.
  • Antidote effective amount means in the context of the invention, an amount of one or more safeners that is suitable, the phytotoxic
  • crop protection agents e.g., herbicides
  • the safeners (B) are suitable for reducing the phytotoxic effects that can occur when using herbicides of the general formula (I) in crops without significantly impairing the effectiveness of these herbicidal active compounds against harmful plants.
  • the field of application of conventional crop protection agents can be considerably extended, e.g. on crops in which the use of herbicides was previously not possible or only possible to a limited extent.
  • the required application rates of the safeners can vary within wide limits and are generally in the range from 0.001 to 5 kg, preferably 0.005 to 2.5 kg of active ingredient per hectare.
  • the herbicidal active compounds of the general formula (I) (A) and the safeners (B) can be applied together (for example as a finished formulation or in the tank-mix process) or in any desired sequence, for example by spraying, pouring and spraying or by granule scattering.
  • the weight ratio herbicide of the general formula (I) (A): safener (B) can vary within wide limits and is preferably in the range from 1: 10,000 to 10,000: 1, in particular from 1: 1000 to 1000: 1.
  • the particular optimum amounts of the general formula (I) (A) and safener (B) are dependent on the type of herbicide and the safener used and on the type and stage of development of the plant stock to be treated and can be determined from case to case by simple to identify routine preliminary tests.
  • the safeners (B) present in the herbicide-safener combination according to the invention can be used for pretreatment of the seed of the crop (for seed dressing, for example) or introduced into the seed furrow before sowing or together with the herbicide before or after be applied to the emergence of the plants.
  • Pre-emergence treatment includes both the treatment of the acreage (including any water on the acreage, eg in rice applications) before sowing and the treatment of the sown, but not overgrown cultivated areas.
  • the seeds e.g., granules, seeds or vegetative propagules such as tubers or sprout parts with buds
  • seedlings are pretreated with the safeners (B), optionally in combination with other agrochemical active ingredients.
  • the active ingredients may be e.g. by seed dressing or the active ingredients and the seed may be added to water or other solvents, and the active ingredients e.g. be absorbed by addition or diffusion in the dipping process or by swelling or pre-germination.
  • the young plants may be e.g. by spraying, dipping or pouring with the safeners, optionally in combination with other agrochemical active ingredients, brought into contact and then transplanted and optionally treated with the herbicides (A).
  • Seedling or seedling treatment can be carried out with the safeners (B) alone or together with other agrochemical active ingredients - such as fungicides, insecticides or plant-strengthening agents, fertilizers or to speed up the swelling and germination processes.
  • the safeners after the pretreatment application can then be applied again before, after or together with one or more herbicides of the formula (I), possibly also in combination with other known herbicides.
  • the pretreatment of the Seeds or seedlings can be achieved an improved long-term effect of safeners.
  • the present invention thus further provides a method for controlling unwanted plants in plant crops, which is characterized in that the components (A) and (B) of the herbicide-safener combination according to the invention on the plants (eg harmful plants such as mono- or dicots Weeds or unwanted crops), the seeds (eg grains, seeds or vegetative propagules such as tubers or sprouts with buds) or the area on which the plants grow (eg the acreage) are applied, eg together or separately.
  • the components (A) and (B) of the herbicide-safener combination according to the invention on the plants eg harmful plants such as mono- or dicots Weeds or unwanted crops
  • the seeds eg grains, seeds or vegetative propagules such as tubers or sprouts with buds
  • the area on which the plants grow eg the acreage
  • one or more safeners (B), preferably one or more, in particular one, compound of groups S1) to S12) before, after or simultaneously with the herbicide (s) of the general formula (I) (A) on the Plants, the seed or the area on which the plants grow (eg the acreage) are applied.
  • the safeners (B) are used for seed treatment.
  • Undesirable plants are understood to mean all plants that grow in places where they are undesirable. This can e.g. Harmful plants (e.g., mono- or dicotyledonous weeds or undesired crops), e.g. also those which are resistant to certain herbicidal active substances such as glyphosate, atrazine, glufosinate or imidazolinone herbicides.
  • Harmful plants e.g., mono- or dicotyledonous weeds or undesired crops
  • certain herbicidal active substances such as glyphosate, atrazine, glufosinate or imidazolinone herbicides.
  • Monocotyledonous weeds originate, for example, from the genera Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyrone, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum. Ischemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
  • Dicotyledonous weeds originate, for example, from the genera Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum.
  • Rorippa Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum, Euphorbia.
  • an effective amount of components (A) and (B) are used to control harmful plants in crops, for example, in economically important crops, e.g. monocotyledonous crops such as cereals (e.g., wheat, barley, rye, oats), rice, corn, millet, or dicotyledonous crops such as sugar beet, oilseed rape, cotton, sunflowers, and legumes, e.g. of the genera Glycine (eg Glycine max such as non-transgenic Glycine max.
  • monocotyledonous crops such as cereals (e.g., wheat, barley, rye, oats), rice, corn, millet, or dicotyledonous crops such as sugar beet, oilseed rape, cotton, sunflowers, and legumes, e.g. of the genera Glycine (eg Glycine max such as non-transgenic Glycine max.
  • Glycine e.g Glycine max such as non-transgenic Glycine
  • Phaseolus eg conventional strains like STS strains
  • transgenic Glycine max eg RR soy or LL soy
  • Phaseolus Phaseolus, Pisum, Vicia and Arachis, or vegetable crops from various botanical groups such as potato, leek, cabbage, carrot, tomato, onion, as well as permanent and plantation crops such as pome and stone fruit, soft fruit, wine, Hevea, bananas, sugar cane, coffee, tea, citrus, nut plantations, Lawn, Palm Cultures and Forest Cultures.
  • the invention also relates to the use of the herbicide-safener combinations according to the invention for controlling undesired plant growth, preferably in plant crops.
  • the herbicidal safener combinations according to the invention can be prepared by known processes, for example as mixed formulations of the individual components, if appropriate with further active ingredients, additives and / or customary formulation auxiliaries, which are then diluted with water in the customary manner, or as so-called tank mixtures by common use Dilution of the separately formulated or partially separately formulated individual components are prepared with water. Also possible is the staggered application (split application) of the separately formulated or partially separately formulated individual components. It is also possible to use the individual components or the herbicide-safener combinations in several portions (sequence application), for. After pre-emergence applications post-emergence or post-emergence applications, followed by mid-late post-emergence applications. Preference is given to the common or timely use of the active ingredients of the respective combination.
  • the herbicide-safener combination according to the invention can also be used for controlling harmful plants in crops of known or yet to be developed genetically modified plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties relate to z. B. the crop in terms of quantity, quality,
  • transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known.
  • Other special properties may be in a tolerance or resistance to abiotic stressors z. As heat, cold, drought, salt and ultraviolet radiation.
  • the application of the herbicide-safener combinations according to the invention or their salts in economically important transgenic crops of useful and ornamental plants eg.
  • cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or cultures of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables.
  • the herbicide-safener combinations according to the invention can be used in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
  • Conventional ways of producing new plants which have modified properties in comparison to previously occurring plants consist, for example, in classical breeding methods and the production of mutants.
  • new plants with altered properties can be generated by means of genetic engineering methods (see, for example, EP-A-0221044, EP-A-0131624). For example, several cases have been described
  • Transgenic crop plants with modified fatty acid composition (WO 91/13972). genetically modified crops with new content or secondary substances z.
  • nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences. With the help of standard methods z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added.
  • adapters or linkers can be attached to the fragments, see, for example, US Pat. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. CoId Spring Harbor Laboratory Press, ColD Spring Harbor, NY; or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996
  • the production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a cosuppression effect or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product.
  • DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
  • the synthesized Protein be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z.
  • the coding region can be linked to DNA sequences that ensure localization in a particular compartment.
  • sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).
  • the expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
  • the transgenic plant cells can be whole by known techniques
  • the transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants.
  • transgenic plants are available, the altered properties by
  • the herbicide-safener combinations according to the invention can be used in transgenic cultures which are resistant to growth substances, such.
  • B. Dicamba or against herbicides the essential plant enzymes, eg. As acetolactate synthases (ALS), EPSP synthases, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, resistant.
  • ALS acetolactate synthases
  • EPSP synthases glutamine synthase
  • HPPD hydroxyphenylpyruvate dioxygenases
  • the invention therefore also relates to the use of the herbicide-safener combinations according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
  • the application of the combinations according to the invention in economically important transgenic crops of useful and ornamental plants, eg. Cereals (e.g., wheat, barley, rye, oats), millet, rice, cassava, and corn, or also sugar beet, cotton, soy, rapeseed, potato, tomato, pea, and other vegetable crops.
  • the invention therefore also relates to the use of the herbicidally active agent according to the invention for controlling harmful plants in transgenic crop plants or crop plants which exhibit tolerance through selective breeding.
  • the herbicides (A) and the safeners (B) may be used together or separately in common formulations e.g. be applied for spraying, pouring, spraying and seed dressing, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active substance-impregnated natural and synthetic substances, Feinstverkapselitch in polymeric materials.
  • the formulations may contain the usual auxiliaries and additives.
  • formulations are prepared in a known manner, for example by mixing the active compounds with extenders, ie liquid solvents, liquefied gases under pressure and / or solid carriers, optionally with the use of surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
  • extenders ie liquid solvents, liquefied gases under pressure and / or solid carriers
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-forming agents.
  • organic solvents can also be used as auxiliary solvent.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as
  • Chlorobenzenes chloroethylenes, or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide or dimethyl sulfoxide, and water.
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide or dimethyl sulfoxide, and water.
  • Suitable solid carriers are: e.g. Ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and silicates; suitable solid carriers for granules are: e.g. crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: e.g.
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates and protein hydrolysates; suitable dispersants are: e.g. Ligninsulfitablaugen and methylcellulose.
  • Adhesives such as carboxymethylcellulose, natural and synthetic, powdery, granular or latex polymers may be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • Other additives may be mineral and vegetable oils.
  • Dyes such as inorganic pigments such as iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90 percent by weight.
  • herbicides (A) and safeners (B) can be used as such or in their formulations also in admixture with other agrochemical active substances, such as known herbicides, for controlling undesired plant growth, e.g. for weed control or to control undesirable crops, e.g. Ready-to-use formulations or tank mixes are possible.
  • herbicides (A) and safeners (B) may be used as such, in the form of their formulations or the forms of use prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules.
  • the application is done in customary, e.g. by pouring, spraying, spraying, sprinkling.
  • the active substances can be applied to the plants, parts of plants, the seed or the acreage (field soil), preferably to the seed or the green plants and plant parts and optionally additionally to the field soil.
  • One possibility of the application is the common application of the active ingredients in the form of tank mixes, with the optimally formulated concentrated formulations of the individual active ingredients are mixed together in the tank with water and the resulting spray mixture is discharged.
  • a common formulation of the combination of active ingredients (A) and (B) according to the invention has the advantage of easier applicability because the amounts of the
  • Components can already be set in the optimum ratio to each other.
  • the adjuvants in the formulation can be optimally matched to one another.
  • combination partners for the herbicidal-safener combination according to the invention in mixture formulations or in the tank mix are known, preferably herbicidal, active ingredients which inhibit, for example, acetolactate synthase, acetyl-coenzyme A carboxylase, PS I, PS II, HPPD , Phytoene desaturase, protoporphyrinogen oxidase, glutamine synthetase, cellulose biosynthesis, 5-enolpyruvylshikimate-3-phosphate synthetase.
  • active ingredients which inhibit, for example, acetolactate synthase, acetyl-coenzyme A carboxylase, PS I, PS II, HPPD , Phytoene desaturase, protoporphyrinogen oxidase, glutamine synthetase, cellulose biosynthesis, 5-enolpyruvylshikimate-3-phosphate synthetase.
  • herbicides known from the literature which can be combined with the mixtures according to the invention (note: the compounds are either with the "common name” according to the International Organization for Standardization (ISO) or with the chemical name , where appropriate together with a customary code number, and always include all forms of use such as acids, salts, esters and isomers such as stereoisomers and optical isomers, one and in some cases also several applications called forms):
  • the formulations present in commercial form are optionally diluted in the customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dust-like preparations, ground or scattered granules and sprayable solutions are usually no longer diluted with other inert substances before use.
  • Seeds or rhizome pieces of monocotyledonous and dicotyledonous harmful plants and of crop plants are placed in peat pots in sandy loam soil, covered with soil and grown in the greenhouse under good growth conditions.
  • harmful plants found in paddy-rice cultivation are cultivated in pots in which water is up to 2 cm above the soil surface. Ten to twenty days after sowing, the test plants are treated at one to three leaf stages.
  • the active ingredients are also added directly to the irrigation water (application in analogy to the so-called granular application) or sprayed on plants and irrigation water.
  • Crop plants were placed in peat pots in sandy loam soil and covered with soil.
  • the herbicidal safener active compound combinations according to the invention formulated as water-soluble powders or suspensions and, in parallel experiments, the correspondingly formulated individual active compounds were then applied to the surface of the cover soil in various dosages with a water application rate of 600 to 800 l / ha.
  • the pots were placed in the greenhouse and kept under good growth conditions for the weeds and the crops.
  • the visual assessment of plant damage or run-on damage occurred after emergence of the test plants after a test period of 2 to 4 weeks in comparison to untreated controls.
  • Seed grains of crops were mixed with the formulated as suspension or emulsion concentrates inventive safeners and water in bottles and shaken well, so that the seeds were evenly coated with the formulation of the respective safener.
  • the seeds or the accumulated plants were then tested in the pre-emergence or post-emergence method according to the experiments of Examples 3.3 and 3.2 with herbicides.

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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)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne une composition contenant (A) un ou plusieurs composés de formule (I), leurs N-oxydes ou leurs sels, R1 représentant un groupe cyclopropyle, 4-Br-phényle ou 4-Cl-phényle, X représentant un atome de chlore ou de brome et R2 représentant un atome d'hydrogène ou un groupe alkyle C1-C14, alcoxyalkyle C2-C14, alcoxyalcoxyalkyle C3-C14, hydroxyalkyle C2-C14 ou benzyle; et (B) un ou plusieurs phytoprotecteurs.
EP09756270A 2008-11-29 2009-11-21 Association d'herbicides et de phytoprotecteurs Withdrawn EP2369931A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP09756270A EP2369931A2 (fr) 2008-11-29 2009-11-21 Association d'herbicides et de phytoprotecteurs

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP08020784A EP2191720A1 (fr) 2008-11-29 2008-11-29 Combinaison d'herbicide-phytoprotecteur
EP09756270A EP2369931A2 (fr) 2008-11-29 2009-11-21 Association d'herbicides et de phytoprotecteurs
PCT/EP2009/008301 WO2010060578A2 (fr) 2008-11-29 2009-11-21 Association d'herbicides et de phytoprotecteurs

Publications (1)

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EP2369931A2 true EP2369931A2 (fr) 2011-10-05

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EP09756270A Withdrawn EP2369931A2 (fr) 2008-11-29 2009-11-21 Association d'herbicides et de phytoprotecteurs

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US (1) US20100137139A1 (fr)
EP (2) EP2191720A1 (fr)
CN (1) CN102227165A (fr)
AR (1) AR075483A1 (fr)
BR (1) BRPI0920968A2 (fr)
WO (1) WO2010060578A2 (fr)

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CN112841197B (zh) * 2019-11-12 2022-02-01 江苏清原农冠杂草防治有限公司 包含嘧啶羧酸苄酯类化合物和psii抑制剂的除草组合物及其应用
CN117099791B (zh) * 2023-10-23 2024-01-30 山东潍坊润丰化工股份有限公司 一种含精异丙甲草胺和扑草净的可分散液剂及其制备方法

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Publication number Publication date
EP2191720A1 (fr) 2010-06-02
BRPI0920968A2 (pt) 2015-08-18
US20100137139A1 (en) 2010-06-03
WO2010060578A3 (fr) 2011-04-21
WO2010060578A2 (fr) 2010-06-03
CN102227165A (zh) 2011-10-26
AR075483A1 (es) 2011-04-06

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