WO1996008488A1 - Heterocyclyl-1,2,4-oxa ou thiadiazolyloxyacetamides herbicides - Google Patents

Heterocyclyl-1,2,4-oxa ou thiadiazolyloxyacetamides herbicides Download PDF

Info

Publication number
WO1996008488A1
WO1996008488A1 PCT/EP1995/003411 EP9503411W WO9608488A1 WO 1996008488 A1 WO1996008488 A1 WO 1996008488A1 EP 9503411 W EP9503411 W EP 9503411W WO 9608488 A1 WO9608488 A1 WO 9608488A1
Authority
WO
WIPO (PCT)
Prior art keywords
optionally substituted
chlorine
fluorine
alkyl
alkoxy
Prior art date
Application number
PCT/EP1995/003411
Other languages
German (de)
English (en)
Inventor
Heinz Förster
Ulrich Heinemann
Hans-Joachim Santel
Markus Dollinger
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 AU35191/95A priority Critical patent/AU3519195A/en
Publication of WO1996008488A1 publication Critical patent/WO1996008488A1/fr

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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond
    • 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

  • HERBICIDE HETEROCYCLYL-1, 2, 4-OXA- BZW. -THIADIAZOLYLOXYACETAMIDE
  • the invention relates to new heterocyclyl-1,2,4-oxa- or -thiadiazolyloxyacetamides, a process for their preparation and their use as herbicides.
  • R 1 represents hydrogen or represents optionally substituted alkyl, alkenyl, alkynyl or aralkyl
  • R 2 represents optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, aryl, alkoxy, alkenyloxy or alkynyloxy, or
  • R 1 and R 2 together with the nitrogen atom to which they are attached form an optionally substituted, saturated or unsaturated nitrogen heterocycle which can contain further heteroatoms and to which a benzo group can be fused,
  • Q stands for oxygen or sulfur and
  • Het represents optionally substituted heterocyclyl.
  • R represents alkyl or arylalkyl, with hydroxyacetamides of the general formula (III)
  • R 1 and R 2 have the meaning given above, if appropriate in the presence of a diluent, if appropriate in the presence of an acid binder and if appropriate in the presence of a catalyst.
  • the invention preferably relates to compounds of the formula (I) in which
  • R 1 represents hydrogen, C 1 -C 8 alkyl (which may be replaced by fluorine, chlorine,
  • Cyano or C 1 -C 4 alkoxy is substituted) for C 2 -C 8 alkenyl (which is optionally substituted by fluorine and / or chlorine), for C 2 -C 8 -
  • Alkynyl or for benzyl (which may be replaced by fluorine, chlorine, C 1 -
  • Cycloalkyl (which is optionally substituted by chlorine and / or C 1 -C 3 alkyl), for C 5 - or C 6 cycloalkenyl, for benzyl (which is optionally substituted by fluorine, chlorine, C 1 -C 4 alkyl and / or C 1 -C 4 alkoxy is substituted) for phenyl (which is optionally substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, C 1 -C 4 alkyl, trifluoromethyl, C 1 -C 4 alkoxy and / or C. 1 -C 4 -
  • Alkylthio is substituted), represents C 1 -C 8 -alkoxy (which is optionally substituted by C 1 -C 4 -alkoxy), or represents C 3 -C 4 -alkenyloxy, or
  • R 1 and R 2 together with the nitrogen atom to which they are attached form a saturated or unsaturated five- to seven-membered nitrogen heterocycle which is optionally mono- to trisubstituted by C 1 -C 3 -alkyl and which is optionally benzene-fused,
  • Het stands for saturated or unsaturated, optionally benzannellated heterocyclyl with 2 to 8 carbon atoms and 1 to 4 heteroatoms - in particular nitrogen, oxygen and / or sulfur atoms - and the possible substituents are preferably selected from the following group:
  • the invention relates in particular to compounds of the formula (I) in which R 1 is methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, n-, i- or s-pentyl (which are each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy) , stands for propenyl, butenyl, propynyl or butynyl, R 2 for methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, n-, i- or s-pentyl, n-, i- or s-hexyl (which are each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy), for propenyl, butenyl, pentenyl, propynyl, butinyl or pentynyl,
  • Chlorine and / or methyl is substituted) or for phenyl (which is in each case optionally substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy or ethoxy), for methoxy, ethoxy, n- or i -Propoxy, n-, i- or s-butoxy, n-, i- or s-pentyloxy (which are each optionally substituted by methoxy or ethoxy), or
  • R 1 and R 2 together with the nitrogen atom to which they are attached, for piperidinyl optionally substituted one to three times by methyl and / or ethyl, for pyrrolidinyl optionally substituted once or twice by methyl and / or ethyl, for perhydroazepinyl or for 1,2,3,4-
  • Formula (II) provides a general definition of the alkylsulfonyl-1,2,4-oxa- or thiadiazole derivatives 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;
  • R preferably represents methyl, ethyl or benzyl and Q preferably represents oxygen or sulfur.
  • the starting materials of the formula (II) are known and / or can be prepared by processes known per se (cf. DE-A 4239727 / LeA 29431, DE-A 4341066 / LeA 29687, WO-A 94/10159).
  • the alkylsulfonyl-1,2,4-oxa- or -thiadiazole derivatives of the formula (II) are obtained if alkylthio-1,2,4-oxa- or -thiadiazole derivatives of the general formula (IV))
  • Het, Q and R have the meaning given above, with an oxidizing agent such as e.g. Hydrogen peroxide, optionally in the presence of a catalyst, e.g. Sodium molybdate, and optionally in the presence of a diluent, such as water and formic acid, at temperatures between -20 ° C and + 100 ° C (see DE-A-4239727).
  • an oxidizing agent such as e.g. Hydrogen peroxide
  • a catalyst e.g. Sodium molybdate
  • a diluent such as water and formic acid
  • Formula (III) provides a general definition of the hydroxyacetic acid amides to be used as starting materials in the process according to the invention for the preparation of compounds of the formula (I).
  • R 1 and R 2 preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R 1 and R 2 .
  • hydroxyacetic acid amides of the formula (III) are known and / or can be prepared by processes known per se (cf. US-P 4509971 and US-P 4645525, furthermore US-P 4334073, DE-OS 3038598, DE-OS 3038636, EP -A 37526, EP-A 348737, DE-OS 3819477).
  • the process according to the invention for the preparation of the new heterocyclyloxa- or thiadiazolyloxyacetamides of the formula (I) is preferably carried out using diluents.
  • diluents include hydrocarbons, such as toluene, xylene or cyclohexane, halogenated hydrocarbons, such as methylene chloride, ethylene chloride, chloroform or Chlorobenzene, ethers, such as, for example, diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, diisobutyl ether, glycol dimethyl ether, tetrahydrofuran and dioxane, alcohols, such as, for example Methanol, ethanol, propanol, isopropanol, butanol, isobutanol, sec-butanol or tert-butanol, ketones, such as, for example, acetone,
  • the salts used here are preferably chlorides or sulfates of alkali or alkaline earth metals, such as sodium chloride, potassium chloride or calcium chloride.
  • Sodium chloride is particularly preferred.
  • the process according to the invention is advantageously carried out using acid binders.
  • strongly basic alkali and alkaline earth metal compounds e.g. oxides such as e.g. Sodium, potassium, magnesium and calcium oxide, hydroxides such as e.g. Sodium, potassium, magnesium and calcium hydroxide, alcoholates such as e.g. Sodium and potassium tert-butoxide and / or carbonates, e.g. Sodium, potassium, magnesium and calcium carbonate used.
  • phase transfer catalyst may prove advantageous in some cases.
  • a phase transfer catalyst examples include: tetrabutylammonium chloride, tetrabutylammonium bromide, tributylmethylphosphonium bromide, trimethyl-C 13 / C 15 -alkyl-ammonium chloride, dibenzyl-dimethylammonium-methylsulfate, dimethyl-C 12 / C 14 -alkyl-benzylammonium-chloride, tetrabutylammonium chloride Krone-6, triethylbenzylammonium chloride, trimethylbenzylammonium chloride, tetraethylammonium bromide.
  • the reaction temperatures can be varied within a wide range in the process according to the invention. In general, temperatures between -50 ° C and +1 10 ° C, preferably at temperatures between -20 ° C
  • the process according to the invention is generally carried out at normal pressure; but it can also be carried out at elevated or reduced pressure, for example between 0.1 and 10 bar.
  • generally 0.5 to 5 mol, preferably 0.8 to 1.5 mol, of hydroxyacetic acid amide of the formula are employed per mol of alkylsulfonyl-1,2,4-oxa- or thiadiazole of the formula (II) (III) a.
  • the reaction components can be combined in any order. In each case, the reaction mixture is stirred until the end of the reaction and worked up by customary methods (cf. the preparation 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. used in the following plants: dicot weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirs Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
  • 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 weed control in annual cultures are used.
  • 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 compounds 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 prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • auxiliary solvents include 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, for example 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 and dimethyl sulfoxide, and water.
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzene
  • 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.
  • non-ionic 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 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 combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.
  • known herbicides are suitable for the mixtures, for example anilides, such as, for example, diflufenican and propanil; Aryl carboxylic acids, such as dichloropicolinic acid re, Dicamba and Picloram; Aryloxyalkanoic acids such as 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters, such as, for example, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; Azinones such as chloridazon and norflurazon; Carbamates such as chlorpropham, desmedipham, phenmedio
  • 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.
  • the preparation and use of the active ingredients according to the invention can be seen from the examples below.
  • 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 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. After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:
  • the compounds according to Preparation Examples 1, 9, 20, 37 and 56 show good activity against weeds with good tolerance to cultivated plants, such as barley and soy.

Landscapes

  • 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)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne de nouveaux hétérocyclyl-1,2,4-oxa ou thiadiazolyloxyacétamides de formule (1), dans laquelle R1 désigne l'hydrogène ou un alkyle, alcényle, alkinyle ou aralkyle, chacun de ces groupes étant éventuellement substitué, R2 désigne un alkyle, alcényle, alkinyle, cycloalkyle, cycloalcényle, aralkyle, aryle, alcoxy, alcényloxy ou alkinyloxy, chacun de ces groupes étant éventuellement substitué, ou bien R1 et R2 forment, conjointement avec l'atome d'azote auquel ils sont liés, un hétérocycle porteur d'azote, saturé ou insaturé, éventuellement substitué, pouvant contenir d'autres hétéro-atomes, et auxquels un groupe benzo peut être annelé, Q désigne un oxygène ou un soufre, et Het désigne un hétérocyclyle éventuellement substitué. L'invention concerne également un procédé de fabrication de ces composés et leur utilisation comme herbicides.
PCT/EP1995/003411 1994-09-13 1995-08-31 Heterocyclyl-1,2,4-oxa ou thiadiazolyloxyacetamides herbicides WO1996008488A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU35191/95A AU3519195A (en) 1994-09-13 1995-08-31 Herbicidal heterocyclyl-1,2,4-oxa- or thia-diazolyloxyacetamides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4432552.5 1994-09-13
DE19944432552 DE4432552A1 (de) 1994-09-13 1994-09-13 Heterocyclyl-1,2,4-oxa- bzw. -thiadiazolyloxyacetamide

Publications (1)

Publication Number Publication Date
WO1996008488A1 true WO1996008488A1 (fr) 1996-03-21

Family

ID=6528082

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/003411 WO1996008488A1 (fr) 1994-09-13 1995-08-31 Heterocyclyl-1,2,4-oxa ou thiadiazolyloxyacetamides herbicides

Country Status (3)

Country Link
AU (1) AU3519195A (fr)
DE (1) DE4432552A1 (fr)
WO (1) WO1996008488A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0018497A1 (fr) * 1979-04-06 1980-11-12 Bayer Ag Azolyloxy-acétamides, procédé pour leur préparation et leur utilisation comme herbicides
US5242890A (en) * 1988-07-07 1993-09-07 Korea Research Institute Of Chemical Technology 1,2,4-oxadiazole derivative, useful as selective herbicide
JPH05286969A (ja) * 1991-12-18 1993-11-02 Agro Kanesho Co Ltd チエニル−アゾリル−オキシアセトアミド誘導体、その製造方法及び該誘導体を有効成分とする除草剤

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0018497A1 (fr) * 1979-04-06 1980-11-12 Bayer Ag Azolyloxy-acétamides, procédé pour leur préparation et leur utilisation comme herbicides
US5242890A (en) * 1988-07-07 1993-09-07 Korea Research Institute Of Chemical Technology 1,2,4-oxadiazole derivative, useful as selective herbicide
JPH05286969A (ja) * 1991-12-18 1993-11-02 Agro Kanesho Co Ltd チエニル−アゾリル−オキシアセトアミド誘導体、その製造方法及び該誘導体を有効成分とする除草剤

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 120, no. 19, 9 May 1994, Columbus, Ohio, US; abstract no. 245115r, page 1053; *

Also Published As

Publication number Publication date
AU3519195A (en) 1996-03-29
DE4432552A1 (de) 1996-03-14

Similar Documents

Publication Publication Date Title
EP0661276A1 (fr) Dérivés de phénylsulfamoyl-pyrimidyl-urée à activité herbicidiques
EP0551821A1 (fr) Dérivés d'acides isoxazolecarboxyliques et leur utilisation comme herbicides
WO1995029902A1 (fr) Phenylaminosulfonylurees substituees utilisees comme herbicides
WO1995022532A1 (fr) Triazolinones substituees et leur utilisation comme herbicides
EP0784616A1 (fr) Sulfonylaminocarbonyltriazolinones comprenant des substituants lies par oxygene et soufre
DE4339863A1 (de) Substituierte Carbamoyltriazole
EP0572893A1 (fr) Fluoro-benzoxazolyloxyacetamides
EP0626380B1 (fr) N-(4-Fluorophényl)-hétéroaryloxyacétamides comme herbicides
EP0824528A1 (fr) Composes sulfonylamino(thio)carbonyltriazoline(thi)ones a substituants aryloxy ou arylthio utilises comme herbicides
EP0537539A1 (fr) 2-(2-Benzoxazolyl-oxy)-acetamides et leur utilisation comme herbicides
EP0758326A1 (fr) Alkylsulfinyl- et alkylsulfonyl-1,2,4,- thiadiazolyloxyacetamides et leur utilisation comme herbicides
EP0588183A1 (fr) Fluoro-benzothiazolyloxyacétamides
WO1995027711A1 (fr) Heterocyclyl-1,2,4-thiadiazolyloxyacetamides et leur utilisation comme herbicides
DE19530767A1 (de) N-(1-Isopropyl-2-methyl-1-propenyl) -heteroaryloxyacetamide
EP0528212A1 (fr) N-azinyl-N'-(2-éthylsulfinyl-phénylsulfonyl)urées comme herbicides
EP0537543A1 (fr) 2-(2-(fluorophényl)-1,3,4-thiadiazol-5-yl-oxy)-acétamides utiles comme herbicides
WO1995032193A1 (fr) Thiadiazolines substituees servant d'herbicides
WO1996008488A1 (fr) Heterocyclyl-1,2,4-oxa ou thiadiazolyloxyacetamides herbicides
EP0815093B1 (fr) Fluorthiadiazolyloxyacetamides herbicides
WO1993024474A1 (fr) Thiadiazolines et leur utilisation comme herbicides
DE19541401A1 (de) 2-[2-(2,6-Difluor-phenyl)-1,3,4-thiadiazol-5-yl-oxy]-acetamide
WO1997040021A1 (fr) N-(2-alkyl-phenylsulfonyl)-n'-(4,6-dimethoxy-2-pyrimidinyl)-(thio)urees herbicides
DE4438178A1 (de) N-Methyl-N-isopropyl-heteroaryloxyacetamide
WO1997008151A1 (fr) Sels de n-(2-cyclopropylcarbonyl-phenylaminosulfonyl)-n'-(4,6-dimethoxy-2-pyrimidinyl)-uree
EP0884304A2 (fr) Procédé pour la préparation du N-(Fluoro-4-phényl)-N-isopropyl-chloracétamide

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU BB BG BR BY CA CN CZ FI HU JP KR KZ LK MX NO NZ PL RO RU SK UA US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: CA