WO1997008160A1 - N-(1-isopropyl-2-methyl-1-propenyl)-heteroaryloxyacetamides et leur utilisation en tant qu'herbicides - Google Patents

N-(1-isopropyl-2-methyl-1-propenyl)-heteroaryloxyacetamides et leur utilisation en tant qu'herbicides Download PDF

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Publication number
WO1997008160A1
WO1997008160A1 PCT/EP1996/003521 EP9603521W WO9708160A1 WO 1997008160 A1 WO1997008160 A1 WO 1997008160A1 EP 9603521 W EP9603521 W EP 9603521W WO 9708160 A1 WO9708160 A1 WO 9708160A1
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WO
WIPO (PCT)
Prior art keywords
methyl
optionally substituted
compounds
formula
general formula
Prior art date
Application number
PCT/EP1996/003521
Other languages
German (de)
English (en)
Inventor
Hans-Jochem Riebel
Yukinoshi Watanabe
Markus Dollinger
Hans-Joachim Santel
Original Assignee
Bayer Aktiengesellschaft
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 Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU68716/96A priority Critical patent/AU6871696A/en
Publication of WO1997008160A1 publication Critical patent/WO1997008160A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • 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
    • A01N43/74—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 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/34—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/13—Oxygen atoms

Definitions

  • the invention relates to N- (l-isopropyl-2-methyl-l-propenyl) heteroaryloxyacetamide, a process for their preparation and their use as herbicides.
  • Het stands for optionally benzannellated and optionally substituted hetero aryl
  • R represents optionally substituted alkyl.
  • X represents halogen, alkylthio, alkylsulfinyl or alkylsulfonyl
  • the invention preferably relates to compounds of the formula (I) in which
  • R represents straight-chain or branched alkyl with 1 to 6 carbon atoms which is optionally substituted by halogen or C ] -C4-alkoxy.
  • the invention relates in particular to compounds of the formula (I) in which
  • R in each case represents methyl, ethyl, n- or i-propyl, n-, i- or s-butyl optionally substituted by fluorine, chlorine, methoxy or ethoxy.
  • reaction sequence in the method according to the invention are outlined by the following formula:
  • Formula (II) provides a general definition of the substituted heteroarenes to be used as starting materials in the process according to the invention for the preparation of the compounds of the general formula (I).
  • Het preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for Het;
  • X preferably represents fluorine, chlorine, bromine, C1-C4-alkylthio, C ⁇ -C4-alkylsulfinyl or Cj-C-i-alkylsulfonyl, in particular chlorine or methylsulfonyl.
  • the starting materials of the formula (II) are known and / or can be prepared by processes known per se (cf. J. Org. Chem. 27 (1962), 2589-2592; EP-A 5501; EP-A 18497; EP-A 165537; EP-A 308740; EP-A 348735; EP-A 348737).
  • Formula (III) provides a general definition of the N- (l-isopropyl-2-methyl-l-propenyl) hydroxyacetamides to be used as starting materials in the process according to the invention for the preparation of the compounds of the formula (I).
  • R preferably or in particular has the meaning which has already been given above as preferred or as particularly preferred for R in the description of the compounds of formula (I).
  • alkali metal acetate e.g. Sodium or potassium acetate
  • acid acceptors e.g. Potassium carbonate and triethylamine
  • N- (l-isopropyl-2-methyl-l-propenyl) chloroacetamides of the formula (IV) are known and / or can be prepared by processes known per se (cf. DE 2526868, US Pat. No. 4258196).
  • organic solvents are suitable as diluents for carrying out the process according to the invention.
  • these include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, pentane, hexane, heptane, petroleum ether, ligroin, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane, dichloromethane, chloroform, tetrachloromethane ; Ethers such as diethyl ether, diisopropyl ether, t-butyl methyl ether, t-pentyl methyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl or diethyl ether, diethylene glycol dimethyl ether or diethyl ether; Ketones such as acetone, butanone,
  • the process according to the invention is preferably carried out in the presence of a suitable reaction auxiliary.
  • a suitable reaction auxiliary All conventional inorganic or organic bases are suitable as such. These include, for example, alkali metal or
  • Alkaline earth metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates such as, for example, lithium, sodium, potassium or calcium hydride, lithium, sodium or potassium amide, sodium or Potassium methylate, sodium or potassium ethylate, sodium or potassium propylate, aluminum isopropylate, sodium or potassium tert-butoxide, sodium or potassium hydroxide,
  • Ammonium hydroxide sodium, potassium or calcium acetate, ammonium acetate, sodium, potassium or calcium carbonate, ammonium carbonate, sodium or potassium hydrogen carbonate, and basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine , N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethylaniline, N, N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-methyl- and 4-methyl-pyridine, 2,4 -Dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclo-octane ( DABCO), di
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between -50 ° C and + 150 ° C, preferably at temperatures between -30 ° C and + 100 ° C, in particular at temperatures between -10 C and + 50 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar.
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers.
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • Sonchus Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
  • Lactuca, cucumis, cucurbita Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sor ⁇ ghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittirpum, Eleocharis, Pas , Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
  • the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • the compounds for weed control in permanent crops e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land and can be used for selective weed control in annual crops.
  • the compounds of formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in dicotyledon crops, especially in the pre-emergence process.
  • the active ingredients can be converted into the usual formulations, such as
  • Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as very fine encapsulations in polymeric substances.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, that is liquid solvents and / or solid Carriers, where appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic 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, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as
  • Possible solid carriers are: e.g. Ammonium salts and natural rock flours, such as kaolins, clays, talc,
  • Chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder 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; come in as dispersants
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, 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, for example 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%.
  • the active compounds according to the invention can also be used in a mixture with known herbicides for combating weeds, finished formulations or tank mixes being possible.
  • herbicides for example anilides, such as e.g. Diflufenican and Propanil; Aryl carboxylic acids, e.g. Dichloropicolinic acid, dicamba and picloram; Aryloxyalkanoic acids, e.g. 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters, e.g. Diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; Azinones, e.g. Chloridazon and norflurazon; Carbamates, e.g. Chloropropham, desmedipham, phenmedipham and propham; Chloroacetanilides, e.g.
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
  • the active compounds 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, sprinkling.
  • the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 10 g and 10 kg of active ingredient per hectare of soil, preferably between 50 g and 5 kg per ha.
  • Methylsulfonyl-5-trifluoromethyl-l, 3,4-thiadiazole and 30 ml of acetone are added and the reaction mixture is stirred for approximately 18 hours at a maximum of 25 ° C. after removing the ice bath. It is then concentrated in a water jet vacuum, the residue is taken up in methylene chloride, washed with water, dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate in a water jet vacuum.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Amount of emulsifier and dilute the concentrate with water to the desired concentration is required.
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the active ingredient preparation is poured onto the floor.
  • the amount of water per unit area is expediently kept constant.
  • the concentration of active substance in the preparation is irrelevant, the only decisive factor is the amount of active substance applied per unit area.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • 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)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne de nouveaux N-(1-isopropyl-2-methyl-1-propényl)-hétéroaryloxyacétamides de formule (I), dans laquelle Het représente hétéroaryle éventuellement annelé en benzène et éventuellement substitué, et R représente alkyle éventuellement substitué. L'invention concerne également un procédé et de nouveaux produits intermédiaires pour leur préparation, ainsi que leur utilisation en tant qu'herbicides.
PCT/EP1996/003521 1995-08-22 1996-08-09 N-(1-isopropyl-2-methyl-1-propenyl)-heteroaryloxyacetamides et leur utilisation en tant qu'herbicides WO1997008160A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU68716/96A AU6871696A (en) 1995-08-22 1996-08-09 N-(1-isopropyl-2-methyl-1-propenyl)heteroaryloxyacetamides and the use thereof as herbicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19530767.4 1995-08-22
DE1995130767 DE19530767A1 (de) 1995-08-22 1995-08-22 N-(1-Isopropyl-2-methyl-1-propenyl) -heteroaryloxyacetamide

Publications (1)

Publication Number Publication Date
WO1997008160A1 true WO1997008160A1 (fr) 1997-03-06

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1996/003521 WO1997008160A1 (fr) 1995-08-22 1996-08-09 N-(1-isopropyl-2-methyl-1-propenyl)-heteroaryloxyacetamides et leur utilisation en tant qu'herbicides

Country Status (3)

Country Link
AU (1) AU6871696A (fr)
DE (1) DE19530767A1 (fr)
WO (1) WO1997008160A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999025702A1 (fr) * 1997-11-18 1999-05-27 American Cyanamid Company N-alcenyle heteroaryloxyacetamides herbicides
WO1999047491A1 (fr) * 1998-03-16 1999-09-23 Korea Research Institute Of Chemical Technology Oxyacetamides de fluorovinyle, leur procede de production et composition herbicide les contenant
US6339042B1 (en) 1999-11-29 2002-01-15 American Cyanamid Co. Herbicidal N-cyclohexadienyl heteroaryloxyacetamides
US6340655B1 (en) 1999-06-22 2002-01-22 American Cyanamid Co. Herbicidal emulsifiable concentrate compositions of dinitroaniline and oxyacetamide herbicides

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2526868A1 (de) * 1974-06-19 1976-01-08 Ciba Geigy Ag Neue ungesaettigte halogenacetamide und deren verwendung in herbiziden und pflanzenwachstumsregulierenden mitteln
EP0161602A2 (fr) * 1984-05-16 1985-11-21 Bayer Ag 6-Chlorobenzazolyloxyacétamide
EP0165537A2 (fr) * 1984-06-20 1985-12-27 Bayer Ag Procédé de préparation d'hétéroaryloxyacétamides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2526868A1 (de) * 1974-06-19 1976-01-08 Ciba Geigy Ag Neue ungesaettigte halogenacetamide und deren verwendung in herbiziden und pflanzenwachstumsregulierenden mitteln
EP0161602A2 (fr) * 1984-05-16 1985-11-21 Bayer Ag 6-Chlorobenzazolyloxyacétamide
EP0165537A2 (fr) * 1984-06-20 1985-12-27 Bayer Ag Procédé de préparation d'hétéroaryloxyacétamides

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999025702A1 (fr) * 1997-11-18 1999-05-27 American Cyanamid Company N-alcenyle heteroaryloxyacetamides herbicides
WO1999047491A1 (fr) * 1998-03-16 1999-09-23 Korea Research Institute Of Chemical Technology Oxyacetamides de fluorovinyle, leur procede de production et composition herbicide les contenant
US6310246B1 (en) * 1998-03-16 2001-10-30 Korea Research Institute Of Chemical Technology Fluorovinloxyacetamides, process for preparing same and herbicidal composition comprising same
US6340655B1 (en) 1999-06-22 2002-01-22 American Cyanamid Co. Herbicidal emulsifiable concentrate compositions of dinitroaniline and oxyacetamide herbicides
US6339042B1 (en) 1999-11-29 2002-01-15 American Cyanamid Co. Herbicidal N-cyclohexadienyl heteroaryloxyacetamides

Also Published As

Publication number Publication date
AU6871696A (en) 1997-03-19
DE19530767A1 (de) 1997-02-27

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