EP0764164A1 - N-heterocyclyl-heteroaryloxyacetamides - Google Patents

N-heterocyclyl-heteroaryloxyacetamides

Info

Publication number
EP0764164A1
EP0764164A1 EP95923207A EP95923207A EP0764164A1 EP 0764164 A1 EP0764164 A1 EP 0764164A1 EP 95923207 A EP95923207 A EP 95923207A EP 95923207 A EP95923207 A EP 95923207A EP 0764164 A1 EP0764164 A1 EP 0764164A1
Authority
EP
European Patent Office
Prior art keywords
pyrimidinyl
chlorine
fluorine
optionally substituted
formula
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Withdrawn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
EP95923207A
Other languages
German (de)
English (en)
Inventor
Heinz Förster
Hans-Joachim Diehr
Hans-Joachim Santel
Markus Dollinger
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 AG
Original Assignee
Bayer 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 AG filed Critical Bayer AG
Publication of EP0764164A1 publication Critical patent/EP0764164A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/36—Nitrogen atoms

Definitions

  • the invention relates to new N-heterocyclyl-heteroaryloxyacetamides, a process and new intermediates for their preparation and their use as herbicides.
  • R represents hydrogen or alkyl which is optionally substituted
  • Het 1 represents optionally benzanellated and optionally substituted hetero aryl
  • Her 2 represents optionally substituted monocyclic or bicyclic heterocyclic
  • Het 1 has the meaning given above and
  • X represents halogen, alkylthio, alkylsulfinyl or alkylsulfonyl
  • the invention preferably relates to compounds of the formula (I) in which
  • R for hydrogen, for CC 8 alkyl (which may be replaced by fluorine,
  • Pyrimidinyl, triazinyl and tetrahydropyranyl where the possible substituents are preferably selected from the series fluorine, chlorine, bromine, cyano, (in each case optionally substituted by fluorine and / or chlorine) -C 8 alkyl, C 2 -C 6 - Alkenyl, C 2 -C 6 alkynyl, C r C 6 alkoxy, C r C 6 alkylthio, C r C 6 alkylsulfonyl and C r C 6 alkylsulfonyl.
  • the invention relates in particular to compounds of the formula (I) in which
  • R for hydrogen, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl
  • Butinyl or stands for benzyl (which is optionally substituted by fluorine, chlorine, cyano, methyl, ethyl, methoxy or ethoxy),
  • Methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, and Her 2 stands for optionally substituted monocyclic or bicyclic heterocyclicl from the series furyl, benzofuryl, tetrahydrofuryl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, quinoline, tetrahydimropyridinyl, trinydyridinyl chloride, trinydyridinyl chloride the possible substituents are preferably selected from the series fluorine, chlorine, bromine, cyano, (each optionally substituted by fluorine and / or chlorine) methyl, ethyl, n- or i-propyl, n-, i-, s- or t- Butyl, prop
  • a very particularly preferred group of the compounds of the formula (I) according to the invention are those in which R and Het 1 have the meaning indicated above as being particularly preferred and Het 2 is furyl or thienyl (in particular thienyl).
  • 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 has 1 preferably or in particular that meaning which has already been given above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for Het 1 ;
  • X preferably represents fluorine, chlorine, bromine, C r C 4 -alkylthio, C r C 4 -alkylsulfonyl or C r C 4 -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 18 49.7; EP-A 165 537; EP-A 308 740; EP-A 348 735; EP-A 348 737).
  • Formula (III) provides a general definition of the hydroxyacetamides to be used further as starting materials in the process according to the invention.
  • Formula (III) has R and Her 2 preferably or in particular those meanings which have already been given above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for R and Her.
  • the starting materials of the formula (III) are known and / or can be prepared by processes known per se (cf. BE-A 897 675; DE-A 3 303 388; DE-A 3 331 873; EP-A 181 018; GB 2 114 566).
  • alkali metal hydroxides e.g. Sodium or potassium hydroxide
  • diluents e.g. Water, methanol and / or ethanol
  • reaction auxiliary e.g. Pyridine
  • amino heterocycles of the formula (V) required as precursors are known and / or can be prepared by processes known per se (cf. Bull. Soc. Chim. France 1986, 259-266).
  • 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, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles, such as acetonitrile, propionitrile or Benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylforman
  • 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 tertiary organic bases are suitable as such. These include, for example
  • 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 + 100 ° C, preferably at temperatures between -30 ° C and + 60 ° C, especially at temperatures between -20 ° C and + 20 ° 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 starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use one of the two components used in each case in a larger excess.
  • the reactions are generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is stirred for several hours at the temperature required in each case.
  • Working up in the process according to the invention is carried out in each case by customary methods (cf. the production examples).
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • Brassica, lactuca, cucumis, cucurbita Brassica, lactuca, cucumis, cucurbita.
  • Alopecurus apera. Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.
  • 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 for selective purposes Weed control can be used in annual crops.
  • the compounds of formula (I) according to the invention are particularly suitable for the selective control of monocotyledon weeds in dicotyledon crops, especially in the pre-emergence process.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymers Fabrics.
  • formulations are prepared in a known manner, e.g. B. 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.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • auxiliary solvents 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 substances such as cyclohexane or paraffins, 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 silicic acid, 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 and 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; suitable dispersants are: e.g. Lignin sulfite liquor 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 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 for weed control in a mixture with known herbicides, 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. Chlorpropham, desmedipham, phenmedipham and propham;
  • anilides such as e.g. Diflufenican and Propanil
  • Aryl carboxylic acids e.
  • Chloroacetanilides e.g. Alachlor, acetochlor, butachlor, metazachlor, metolochlor, pretilachlor and propachlor; Dinitroanilines, e.g. Oryzalin, pendimethalin and trifluralin; Diphenyl ethers, e.g. Acifluorfen, Bifenox, Fluoroglycfen, Fomesafen, Halosafen, Lactofen and Oxyfluorfen; Ureas, e.g. Chlorotoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron;
  • Dinitroanilines e.g. Oryzalin, pendimethalin and trifluralin
  • Diphenyl ethers e.g. Acifluorfen, Bifenox, Fluoroglycfen, Fomesafen, Halosafen, Lactofen and Oxyflu
  • Hydroxylamines e.g. Alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; Imidazolinones, e.g. Imazethapyr, imazamethabenz, imazapyr and imazaquin; Nitriles, e.g. Bromoxynil, dichlobenil and ioxynil; Oxyacetamides, e.g. Mefenacet; Sulfonylureas, e.g.
  • Amidosulfon bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primi sulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; Thiol carbamates, e.g. Butylates, cycloates, dialallates, EPTC, esprocarb, molinates, prosulfocarb, thiobencarb and triallates; Triazines, e.g.
  • Atrazin cyanazin, simazin, simetryne, terbutryne and terbutylazine; Triazinones, e.g. Hexazinone, metamitron and metribuzin; Others, such as Aminotriazole, Benfuresate, Bentazone, Cinmethylin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, Ethofumesate, Fluorochloridone, Glufosinate, Glyphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and Tridiphane.
  • Triazinones e.g. Hexazinone, metamitron and metribuzin
  • Others such as Aminotriazole, Benfuresate, Bentazone, Cinmethylin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, Ethofumesate, Fluorochloridone,
  • Insecticides acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure are 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 customary manner, for example by watering, spraying, spraying or scattering.
  • 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.
  • Example 26 The compound mentioned in Table 1 as Example 26 can expediently be prepared as follows:
  • Example 25 The compounds mentioned in Table 1 as Example 25 and Example 27 can be prepared in an analogous manner.
  • Solvent 5 parts by weight of acetone emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Seeds of the test plants are sown in normal soil. After 24 hours, the floor is poured with the active ingredient preparation. 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. After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • the compound according to Preparation Example 1 shows very good tolerance to crop plants, such as Beets, strong

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

Abstract

De nouveaux N-hétérocyclyl-hétéroaryloxyacétamides, à l'exception du composé 2-(2-benzothiazolyloxy)-N-(4-morpholinyl)-acétamide, ont la formule (I), dans laquelle R désigne hydrogène ou alcoyle, alcényle, alcinyle ou arylalcoyle le cas échéant substitués; Het1 désigne hétéroaryle le cas échéant cyclisé en benzène et substitué; et Het2 désigne hétérocyclyle monocyclique ou bicyclique le cas échéant substitué. L'invention concerne également un procédé et de nouveaux produits intermédiaires de préparation de ces nouveaux composés et leur utilisation comme herbicides.
EP95923207A 1994-06-10 1995-05-29 N-heterocyclyl-heteroaryloxyacetamides Withdrawn EP0764164A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4420337 1994-06-10
DE19944420337 DE4420337A1 (de) 1994-06-10 1994-06-10 N-Heterocyclyl-heteroaryloxyacetamide
PCT/EP1995/002034 WO1995034560A1 (fr) 1994-06-10 1995-05-29 N-heterocyclyl-heteroaryloxyacetamides

Publications (1)

Publication Number Publication Date
EP0764164A1 true EP0764164A1 (fr) 1997-03-26

Family

ID=6520296

Family Applications (1)

Application Number Title Priority Date Filing Date
EP95923207A Withdrawn EP0764164A1 (fr) 1994-06-10 1995-05-29 N-heterocyclyl-heteroaryloxyacetamides

Country Status (5)

Country Link
EP (1) EP0764164A1 (fr)
JP (1) JPH10501538A (fr)
AU (1) AU2786495A (fr)
DE (1) DE4420337A1 (fr)
WO (1) WO1995034560A1 (fr)

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5725556B1 (fr) * 1971-05-07 1982-05-29
DE2961415D1 (en) * 1978-05-20 1982-01-28 Bayer Ag Heteroaryloxy-acetamides, process for their preparation and their use as herbicides
FR2582514B1 (fr) * 1985-05-30 1988-02-19 Rhone Poulenc Sante Medicaments a base d'amides, nouveaux amides et leur preparation
JPS62153283A (ja) * 1985-12-27 1987-07-08 Tokuyama Soda Co Ltd ピラゾ−ル化合物
JPS63313773A (ja) * 1987-06-16 1988-12-21 Tokuyama Soda Co Ltd ピラゾ−ル化合物
JPH0684363B2 (ja) * 1989-08-23 1994-10-26 株式会社トモノアグリカ １、２、３―チアジアゾール誘導体、その製造法及び除草剤
JP2895196B2 (ja) * 1989-09-28 1999-05-24 株式会社トクヤマ リンゴ用摘花剤
JPH05112547A (ja) * 1991-08-28 1993-05-07 Tosoh Corp チアジアゾロキシ酢酸アミド誘導体及びそれを有効成分とする除草剤
JPH0692804A (ja) * 1992-09-11 1994-04-05 Tokuyama Soda Co Ltd リンゴ用摘花剤
JPH0733752A (ja) * 1993-07-16 1995-02-03 Sankyo Co Ltd ジフェニルピラジン誘導体及び除草剤

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9534560A1 *

Also Published As

Publication number Publication date
WO1995034560A1 (fr) 1995-12-21
AU2786495A (en) 1996-01-05
DE4420337A1 (de) 1995-12-14
JPH10501538A (ja) 1998-02-10

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