EP1298996A1 - Selektive herbizide auf basis von heteroaryloxy-acetamiden - Google Patents

Selektive herbizide auf basis von heteroaryloxy-acetamiden

Info

Publication number
EP1298996A1
EP1298996A1 EP01943335A EP01943335A EP1298996A1 EP 1298996 A1 EP1298996 A1 EP 1298996A1 EP 01943335 A EP01943335 A EP 01943335A EP 01943335 A EP01943335 A EP 01943335A EP 1298996 A1 EP1298996 A1 EP 1298996A1
Authority
EP
European Patent Office
Prior art keywords
methyl
ethyl
chloro
phenyl
dihydro
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Withdrawn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
EP01943335A
Other languages
German (de)
English (en)
French (fr)
Inventor
Dieter Feucht
Peter Dahmen
Mark Wilhelm Drewes
Rolf Pontzen
Mathias Kremer
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 CropScience AG
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
Priority claimed from DE10041619A external-priority patent/DE10041619A1/de
Priority to EP10158915.8A priority Critical patent/EP2243362B1/de
Priority to EP10158916.6A priority patent/EP2243363B1/de
Priority to EP10158913.3A priority patent/EP2243361B1/de
Priority to EP10158924A priority patent/EP2243366A3/de
Priority to EP10158925A priority patent/EP2243367A3/de
Priority to DK05005219.0T priority patent/DK1552746T3/en
Priority to EP10158933A priority patent/EP2243370A2/de
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Priority to EP05005219.0A priority patent/EP1552746B1/de
Priority to EP10158918A priority patent/EP2243365A3/de
Priority to EP10158929A priority patent/EP2243368A3/de
Priority to EP10158917.4A priority patent/EP2243364B1/de
Priority to EP10158932A priority patent/EP2243369A3/de
Publication of EP1298996A1 publication Critical patent/EP1298996A1/de
Withdrawn legal-status Critical Current

Links

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
    • A01N43/72—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 invention relates to new selective herbicidal, synergistic active ingredient combinations which consist of known heteroaryloxyacetamides on the one hand and known herbicidally active compounds and / or compounds which improve the tolerance of crop plants on the other hand and which are used with particularly good success for selective weed control in various crop plants can.
  • Heteroaryloxyacetamides as strong herbicides which are particularly effective against monocotyledon weeds, are the subject of a number of patent applications (cf. EP-A 5501, EP-A 18497, EP-A 29171, EP-A 94514, EP-A 100044, EP-A 100045, EP -A 161602, EP-A 195237, EP-A 348734, EP-A 348737, DE-A 4317323).
  • EP-A 5501, EP-A 18497, EP-A 29171, EP-A 94514, EP-A 100044, EP-A 100045, EP -A 161602, EP-A 195237, EP-A 348734, EP-A 348737, DE-A 4317323 are the subject of a number of patent applications.
  • active substance combinations are heteroaryloxyacetamides and other herbicidally active compounds to achieve a synergistic effect (cf. WO-A 94/02014, WO-A-96/07323, WO-A-96/11575, WO-A-96/17519 , WO-A-
  • the invention relates to selective herbicidal compositions, characterized by an effective content of an active ingredient combination consisting of
  • Ar represents phenyl which is optionally substituted by halogen, C 4 -C 4 -alkyl or C 4 -C 4 -haloalkyl,
  • Het is thiadiazolyl which is substituted by halogen or by C1-C4-alkyl or phenyl which is optionally substituted by halogen, and
  • R represents alkyl, alkenyl or alkynyl each having up to 4 carbon atoms
  • Ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazole carboxylate isoxadifen-ethyl
  • diethyl l- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole -3,5-dicarboxy-lat mefenpyr-diethyl
  • 2-dichloromethyl-2-methyl-1,3-dioxolane MG-191, 1,8-naphthalic acid anhydride, ⁇ - (1,3-dioxolane-2 -yl-methoximino) -phenylaceto-nitrile (oxabetrinil), 2,2-dichloro-N- (1,3-dioxolan-2-yl-methyl) -N- (2-propenyl) -acetamide (PPG-1292), 3-dichloroacetyl-2,2-dimethyl-oxazolidine (R-2
  • Ar preferably represents phenyl optionally substituted by fluorine, chlorine, bromine, methyl, ethyl or trifluoromethyl.
  • Het preferably stands for 1,2,4-thiadiazolyl or 1,3,4-thiadiazolyl, which by fluorine, chlorine, bromine or by optionally by fluorine and / or Chlorine substituted methyl, ethyl, n- or i-propyl or phenyl is substituted.
  • R preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 2-propenyl, l-methyl-2-propenyl, 2-butenyl, 2-propynyl, 1- Methyl 2-propynyl, 2-butynyl.
  • Ar particularly preferably represents phenyl optionally substituted by fluorine, chlorine, bromine, methyl or trifluoromethyl.
  • Het is particularly preferably 1,2,4-thiadiazolyl or 1,3,4-thiadiazolyl, which is substituted by fluorine, chlorine, bromine or by methyl, ethyl or phenyl which are optionally substituted by fluorine and / or chlorine.
  • R particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-
  • Ar very particularly preferably represents phenyl optionally substituted by fluorine or chlorine.
  • Het very particularly preferably represents 1,3,4-thiadiazolyl which is substituted by chlorine, bromine or by fluorine- and / or chlorine-substituted methyl.
  • R very particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
  • Examples of the compounds of the formula (I) to be used as mixture partners according to the invention are: Ni-propyl-N-phenyl- ⁇ - (5-trifluoromethyl-l, 3,4-thiadiazol-2-yl-oxy) -acetamide, Ni-propyl-N- (2-chlorophenyl) - ⁇ - (5th -trifluora ⁇ ethyl-l, 3,4-thiadiazol-2-yl-oxy) -acetamide, Ni-propyl-N- (3-chlorophenyl) - ⁇ - (5-trifluoromethyl-l, 3,4-thiadiazol-2 -yl-oxy) -acetamide, Ni-propyl-N- (4-chlorophenyl) - ⁇ - (5-trifluoromethyl-l, 3,4-thiadiazol-2-yl-oxy) - acetamide, Ni Propyl-N- (2-fluoro-phenyl) - ⁇ - (5-trifluoromethyl-1, 3,
  • the active substances of group 2 can be assigned to their chemical structure according to the following active substance classes:
  • Amides e.g. beflubutamide
  • aryl heterocycles e.g. azafenidin, benzfendizone
  • Butroxydim, Clefoxydim, Cycloxydim), dinitroanilines e.g. Benfluralin, Oryzalin
  • imidazoxones e.g. Imazamoxolinone
  • Isoxachlortole e.g. Isoxachlortole
  • pyridines e.g. Thiazopyr
  • pyrimidinyl (thio) benzoates e.g. Pyribenz-oxim, Pyriftalid, Pyriminobac-methyl, Pyrithiobac-sodium
  • sulfonylureas e.g.
  • Azimsulfuron Flupyrsulfuron-methyl-sodium, Foramsulfuron-methyl- Iodosulfuron sodium, mesosul Someon, trifloxysulfuron, triflusulfuron-methyl), tetrazolinones (e.g.
  • Fentrazamides Fentrazamides
  • triazoles e.g. amitroles
  • triazolinones e.g. flucarbazone-sodium, Procarbazone-sodium
  • triazolopyrimidines e.g. cloransulam-methyl, diclosulam, florasulam
  • triketones e.g. mesotrione
  • mixture components from the active ingredients of group 2 are:
  • Azimsulfuron Beflubuta id, Butafenacil-allyl, Cinidon-ethyl, Cloransulam-methyl, Clefoxydim, Diclosulam, Fenoxaprop-P-ethyl, Florasulam, Flupyrsul possiblyon-methyl-sodium, Foramsulmron, Imazamox, Iodosulfuron-methyl-sodium, Oxox, Isox , Procarbazone-sodium, pyriftalid, pyrithiobac-sodium, quinclorac, trifloxysulfuron.
  • beflubutamide is of particular interest as a mixture component.
  • butafenacil-allyl is of particular interest as a mixture component.
  • cinidon-ethyl is of particular interest as a mixture component.
  • Clefoxydim is also of particular interest as a mixture component.
  • cloransulam-methyl is also of particular interest as a mixture component.
  • flupyrsulfuron-methyl-sodium is of particular interest as a mixture component.
  • imazamox is also of particular interest as a mixture component.
  • iodosulfuron-methyl-sodium is of particular interest as a mixture component.
  • mesosullayson is also of particular interest as a mixture component.
  • oxaziclomefone is also of particular interest as a mixture component.
  • Procarbazone-sodium from this group is of particular interest as a mixture component.
  • agents according to the invention preferably contain one or two active substances from group 1, one to three active substances from group 2 and optionally an active substance from group 3.
  • the agents according to the invention contain an active ingredient of group 1, one or two active ingredients of group 2 and optionally an active ingredient of group 3.
  • Active ingredients of group 2 with a largely good crop tolerance have a particularly high herbicidal activity and can be used in various crops, in particular in barley, potatoes, corn, rice, soybeans and wheat, for the selective control of monocotyledonous and dicotyledonous weeds and that they can also be used for Control of monocot and dicot weeds in the semi and non-selective range can be used.
  • the herbicidal activity of the active compound combinations according to the invention consisting of compounds from groups 1 and 2 listed above is considerably higher than the sum of the effects of the individual active compounds.
  • the new active ingredient combinations are well tolerated in many crops, and the new active ingredient combinations also combat weeds that are otherwise difficult to control.
  • the new active ingredient combinations thus represent a valuable addition to the herbicides.
  • the synergistic effect of the active compound combinations according to the invention is particularly pronounced at certain concentration ratios.
  • the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges.
  • 1 part by weight of active Substance of the formula (I) 0.01 to 1000 parts by weight, preferably 0.02 to 500 parts by weight and particularly preferably 0.05 to 100 parts by weight of active ingredient or active ingredients of group 2.
  • the group 3 compounds listed above are particularly suitable, the harmful effect of active compounds of the formula ( I) and their salts, if appropriate also in combination with one or more of the active ingredients of group 2 mentioned above, to be completely removed from the crop plants without impairing the herbicidal activity against the weeds.
  • the advantageous effect of the crop plant compatibility of the active compound combinations according to the invention is also particularly pronounced at certain concentration ratios.
  • the weight ratios of the active ingredients in the active ingredient combinations can be varied within relatively large ranges. In general, 1 part by weight of active compound of the formula (I) or mixtures thereof are present
  • Active substances of group 2 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight and particularly preferably 0.1 to 10 parts by weight of active substance or active substances of group 3.
  • Plants are understood to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground plant parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds and
  • Roots, tubers and rhiozomes are listed.
  • the plant parts also include vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and parts of plants with the active compounds takes place directly or by acting on their surroundings, living space or storage space according to the customary treatment methods, for example by dipping, spraying, evaporating, atomizing, scattering, spreading and, in the case of propagation material, in particular seeds, by - or multi-layer wrapping.
  • the plants obtained by biotechnological and genetic engineering methods or by a combination of these methods those plants are emphasized which tolerate so-called 4-HPPD, EPSP and / or PPO materials, such as, for example, acuron plants.
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • the active ingredient combinations to be used according to the invention can be used both in conventional cultivation processes (row crops with a suitable row width) in plantation crops (for example wine, fruit, citrus) and in industrial and track systems, on paths and squares, but also for stubble treatment and with the minimum tillage process become. They are also suitable as burners (herb killing e.g. in potatoes) or as defoliants (e.g. in cotton). They are also suitable for use on fallow land. Other areas of application are tree nurseries, forestry, grassland and ornamental plant growing.
  • the active substance combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents and / or solid carriers
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • water is used as an extender, e.g. also organic
  • Solvents are used as auxiliary solvents.
  • the following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable
  • Oils 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 and dimethyl sulfoxide, and water.
  • ketones such as Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide
  • e.g. Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates,
  • Alkyl sulfates, aryl sulfonates and protein hydrolyzates Possible dispersants are: e.g. Lignin sulfate leachate and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarinv, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarinv, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active ingredients, preferably between 0.5 and 90%.
  • the active compound combinations according to the invention are generally used in the form of finished formulations.
  • the active substances contained in the active substance combinations can, however, also be mixed in individual formulations when used, that is to say applied in the form of tank mixtures.
  • the new combinations of active ingredients can furthermore also be used in a mixture with other known herbicides, ready-to-use formulations or tank mixes being possible.
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, growth agents, plant nutrients and agents which improve soil structure, is also possible.
  • mineral or vegetable oils which are compatible with plants (e.g. the commercial preparation "Oleo DuPont 11E") or ammonium salts such as e.g. Include ammonium sulfate or ammonium rhodanide.
  • the new combinations of active substances can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, dusting or scattering.
  • the active ingredient combinations according to the invention can be applied before and after emergence of the plants, that is to say in the pre-emergence and post-emergence process. They can also be worked into the soil before sowing.
  • X % damage by herbicide A (active ingredient of the formula I) at p kg / ha
  • Y % damage by herbicide B (active ingredient of the formula II) at q kg / ha
  • the effect of the combination is super-additive, that is, it shows a synergistic effect.

Landscapes

  • 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)
EP01943335A 2000-05-22 2001-05-09 Selektive herbizide auf basis von heteroaryloxy-acetamiden Withdrawn EP1298996A1 (de)

Priority Applications (12)

Application Number Priority Date Filing Date Title
EP10158932A EP2243369A3 (de) 2000-05-22 2001-05-09 Selektive Herbizide auf Basis von Heteroaryloxy-acetamiden
EP10158933A EP2243370A2 (de) 2000-05-22 2001-05-09 Selektive Herbizide auf Basis von Heteroaryloxy-acetamiden
EP10158913.3A EP2243361B1 (de) 2000-05-22 2001-05-09 Selektive Herbizide auf Basis von Heteroaryloxy-acetamiden
EP10158924A EP2243366A3 (de) 2000-05-22 2001-05-09 Selektive Herbizide auf Basis von Heteroaryloxy-acetamiden
EP10158925A EP2243367A3 (de) 2000-05-22 2001-05-09 Selektive Herbizide auf Basis von Heteroaryloxy-acetamiden
DK05005219.0T DK1552746T3 (en) 2000-05-22 2001-05-09 Selective herbicides based on heteroaryloxy-acetamides
EP05005219.0A EP1552746B1 (de) 2000-05-22 2001-05-09 Selektive Herbizide auf Basis von Heteroaryloxy-acetamiden
EP10158915.8A EP2243362B1 (de) 2000-05-22 2001-05-09 Selektive Herbizide auf Basis von Heteroaryloxy-acetamiden
EP10158916.6A EP2243363B1 (de) 2000-05-22 2001-05-09 Selektive Herbizide auf Basis von Heteroaryloxy-acetamiden
EP10158918A EP2243365A3 (de) 2000-05-22 2001-05-09 Selektive Herbizide auf Basis von Heteroaryloxy-acetamiden
EP10158929A EP2243368A3 (de) 2000-05-22 2001-05-09 Selektive Herbizide auf Basis von Heteroaryloxy-acetamiden
EP10158917.4A EP2243364B1 (de) 2000-05-22 2001-05-09 Selektive Herbizide auf Basis von Heteroaryloxy-acetamiden

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE10025306 2000-05-22
DE10025306 2000-05-22
DE10041619A DE10041619A1 (de) 2000-05-22 2000-08-24 Selektive Herbizide auf Basis von Heteroaryloxyacetamiden
DE10041619 2000-08-24
PCT/EP2001/005242 WO2001089301A1 (de) 2000-05-22 2001-05-09 Selektive herbizide auf basis von heteroaryloxy-acetamiden

Related Child Applications (5)

Application Number Title Priority Date Filing Date
EP10158917.4A Division EP2243364B1 (de) 2000-05-22 2001-05-09 Selektive Herbizide auf Basis von Heteroaryloxy-acetamiden
EP10158916.6A Division EP2243363B1 (de) 2000-05-22 2001-05-09 Selektive Herbizide auf Basis von Heteroaryloxy-acetamiden
EP05005219.0A Division EP1552746B1 (de) 2000-05-22 2001-05-09 Selektive Herbizide auf Basis von Heteroaryloxy-acetamiden
EP10158913.3A Division EP2243361B1 (de) 2000-05-22 2001-05-09 Selektive Herbizide auf Basis von Heteroaryloxy-acetamiden
EP10158915.8A Division EP2243362B1 (de) 2000-05-22 2001-05-09 Selektive Herbizide auf Basis von Heteroaryloxy-acetamiden

Publications (1)

Publication Number Publication Date
EP1298996A1 true EP1298996A1 (de) 2003-04-09

Family

ID=26005781

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01943335A Withdrawn EP1298996A1 (de) 2000-05-22 2001-05-09 Selektive herbizide auf basis von heteroaryloxy-acetamiden

Country Status (15)

Country Link
US (2) US6967188B2 (ja)
EP (1) EP1298996A1 (ja)
JP (1) JP2003533545A (ja)
KR (1) KR100781758B1 (ja)
CN (1) CN1430471A (ja)
AU (2) AU2001265936B2 (ja)
BR (1) BRPI0111008B1 (ja)
CA (1) CA2409215A1 (ja)
CZ (1) CZ301614B6 (ja)
HR (1) HRP20021022A2 (ja)
HU (1) HU230428B1 (ja)
MX (1) MXPA02011468A (ja)
PL (1) PL218432B1 (ja)
SK (1) SK287461B6 (ja)
WO (1) WO2001089301A1 (ja)

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