EP0652883A1 - Derives heterocycliques de pyrimidinedione et leur utilisation comme herbicides - Google Patents

Derives heterocycliques de pyrimidinedione et leur utilisation comme herbicides

Info

Publication number
EP0652883A1
EP0652883A1 EP93917695A EP93917695A EP0652883A1 EP 0652883 A1 EP0652883 A1 EP 0652883A1 EP 93917695 A EP93917695 A EP 93917695A EP 93917695 A EP93917695 A EP 93917695A EP 0652883 A1 EP0652883 A1 EP 0652883A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
haloalkyl
halogen
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Withdrawn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
EP93917695A
Other languages
German (de)
English (en)
Inventor
Matthias SCHÄFER
Karlheinz Drauz
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.)
Evonik Operations GmbH
Original Assignee
Degussa GmbH
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 Degussa GmbH filed Critical Degussa GmbH
Publication of EP0652883A1 publication Critical patent/EP0652883A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Definitions

  • the present invention relates to new types
  • EP-Bl 0 070 389) can be used as herbicides.
  • the object of the present invention therefore includes compounds of the formula I in which
  • X represents O, S, CH 2 , CHF, CF 2 , CHCl, CHBr, CHOCH 2 F, CHOCF 3 or CHOCH 2 CF 3 ,
  • n 1 or 2
  • R 1 and R 2 independently of one another, for hydrogen, hydroxy, halogen, (C 1 - C 4 ) alkyl, (C 1 - C 4 ) alkoxy, (C 1 - C 4 ) haloalkyl or (C 1 - C 4 ) Haloalkoxy stand,
  • R 3 and R 4 independently of one another, for hydrogen, hydroxy, halogen, cyano, (C 1 -C 4 ) alkyl,
  • w O or S
  • R 5 represents hydrogen or halogen
  • R 7 represents hydrogen, (C 1 - C 8 ) alkyl
  • CH CHCO 2 R 11
  • CO 2 N CR 14 R 15 , NO 2 , CN, NHSO 2 R 16 or
  • R 8 is hydrogen, (C 1 - C 3 ) alkyl
  • R 9 represents hydrogen, (C 1 - C 3 ) alkyl
  • R 10 for (C 1 -C 6 ) alkyl, (C 1 -C 6 ) haloalkyl
  • Cycloalkylalkyl (C 2 - C 4 ) carboxyalkyl
  • Halogen (C 1 -C 3 ) alkyl or (C 1 -C 3 ) haloalkyl;
  • R 12 and R 14 independently of one another, represent hydrogen or (C 1 -C 4 ) alkyl
  • R 13 and R 15 independently of one another, for
  • R 12 and R 13 as - (CH 2 ) 5 -, - (CH 2 ) 4 - or
  • -CH 2 CH 2 OCH 2 CH 2 - can be combined to form rings, it being possible for one or more H atoms in each ring to be optionally substituted by (C 1 - C 3 ) alkyl-, phenyl- or benzyl,
  • R 14 and R 15 together with the carbon to which they are attached can form a (C 3 -C 8 ) cycloalkyl group
  • R 16 represents (C 1 -C 4 ) alkyl or (C 1 -C 4 ) haloalkyl
  • R 17 represents hydrogen or (C 1 - C 3 ) alkyl
  • R 18 is (C 1 -C 6 ) alkyl, (C 3 -C 6 ) alkenyl or
  • n 0, 1 or 2.
  • alkyl alone or in the compound name such as “alkylthlo” or “haloalkyl”, includes a straight or branched chain, e.g. B. methyl,
  • Alkoxy includes methoxy, ethoxy, n-propyloxy, isopropyloxy and the various
  • Alkenyl includes straight or branched alkenes, e.g. B., 1-propenyl, 2-propenyl, 3-propenyl and the various butenyl isomers.
  • Cycloalkyl includes cyclopropyl, cyclobutyl,
  • Haloalkyl means fluorine, chlorine, bromine or iodine.
  • alkyl when “haloalkyl” is used in the compound name, alkyl can be partially or completely substituted with halogen atoms, which in turn can be the same or different.
  • haloalkyl examples include CH 2 CH 2 F, CF 2 CF 3 and CH 2 CHFCl.
  • X represents O, S, CH 2 , CHF, CF 2 , CHCl, CHBr, CHOCHF 2 , CHOCF 3 or CHOCH, CF 3 ,
  • R 1 and R 2 independently of one another, represent hydrogen, hydroxy, fluorine, chlorine, bromine, methyl or methoxy,
  • R 3 and R 4 independently of one another, for hydrogen, hydroxyl, fluorine, chlorine, bromo, cyan,
  • w 0 or S
  • n 0, 1, 2
  • R 6 represents halogen or CN
  • R 7 is hydrogen, (C 1 - C 4 ) alkyl, (C 1
  • CO 2 N CR 14 R 15 , NHSO 2 R 16 or NHSO 2 NHR 16 , R 8 represents hydrogen, (C 1 - C 3 ) alkyl or
  • R 9 represents hydrogen, (C 1 - C 3 ) alkyl or
  • R 1 0 (C 1 - C 4) alkyl, (C 1 - C 4) haloalkyl,
  • R 11 is for (C 1 -C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl,
  • Halogen (C 1 - C 3 ) alkyl or (C 1 - C 3 ) haloalkyl, (C 4 - C 8 ) trialkylsiiylalkyl, (C 3 - C 4 ) cyanoalkyl, (C 3 - C 6 ) halocycloalkyl, (C 3 - C 6 ) haloalkenyl.
  • R 14 and R 15 together with the carbon to which they are attached can form a (C 3 -C 6 ) cycloalkyl group
  • R 16 represents (C 1 -C 4 ) alkyl or (C 1 -C 4 ) haloalkyl
  • R 17 represents hydrogen or (C 1 -C 3 ) alkyl
  • R 18 is (C 1 -C 4 ) alkyl, (C 3 -C 4 ) alkenyl or
  • R 12 and R 13 When R 12 and R 13 are combined to form a ring, they form a pyrrolidinyl, piperidinyl or with the N atom to which they are attached
  • n 1 or 2
  • R 1 and R 2 represent hydrogen
  • R 3 and R 4 represent hydrogen, Q means
  • w O or S
  • R 5 represents hydrogen, fluorine or chlorine
  • R 6 represents chlorine, bromine or cyan
  • R 8 and R 9 independently of one another, are hydrogen
  • R 11 represents (C 1 -C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl,
  • R 12 represents hydrogen or (C 1 - C 2 ) alkyl
  • R 12 and R 13 can be - (CH 2 ) 5 -, -CH 2 ) 4 - or
  • -CH 2 CH 2 OCH 2 CH 2 - can be combined to form rings, where one or more H atoms in each ring can optionally be substituted by (C 1 - C 2 ) alkyl,
  • R 17 represents hydrogen or (C 1 - C 2 ) alkyl
  • R 18 is (C 1 -C 2 ) alkyl, (C 3 -C 4 ) alkenyl or
  • X represents CH 2 , O or S
  • n 1 or 2
  • R 1 and R 2 represent hydrogen
  • R 3 and R 4 represent hydrogen
  • R 5 represents fluorine or chlorine
  • R 6 represents chlorine
  • R 11 is for (C 1 -C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl,
  • the invention relates both to the individual possible stereoisomers of the formula I and to mixtures of these isomers.
  • novel heterocyclic compounds of general formula I are obtained according to the present invention when aryl isocyanates
  • R represents hydrogen, (C 1 -C 4 ) alkyl or active ester, according to method A, optionally in the presence of an acid acceptor and optionally in the presence of a thinner
  • Another object of the invention is
  • Another object of the invention is method D for the preparation of compounds of formula I, which is explained below, wherein m, X, R 1 , R 2 , R 3 , R 4 and Q have the meaning given above and wherein a compound of Formula II with a compound of formula XI, optionally in the presence of a
  • Acid acceptor and optionally in the presence of a diluent is brought to reaction and thereby
  • halogenated hydrocarbon such as chloroform
  • Organic bases are preferably used as bases, for example organic amines such as triethylamine or pyridine.
  • R H
  • the reaction is carried out in water as a solvent or, preferably, in a two-phase water / organic solvent system.
  • an inorganic base for example an alkali metal or
  • Hydrogen carbonate such as sodium hydroxide or also
  • Potassium carbonate or together with an organic base such as, for example, an organic amine such as triethylamine, and then compounds of the formula II, dissolved in an inert solvent such as, for example, toluene, chlorobenzene or chloroform, are added.
  • the reaction mixture is then kept at temperatures between -40 ° C. and + 50 ° C., preferably -10 ° C. and + 10 ° C., for several days, preferably between 3 and 50 hours.
  • the aqueous phase is then adjusted to a pH between 1 and 3 using acid, preferably an inorganic acid such as aqueous hydrochloric or sulfuric acid.
  • acid preferably an inorganic acid such as aqueous hydrochloric or sulfuric acid.
  • Amines of the formula III are known and can be prepared analogously to the known methods; see, for example, M.Seklya et al., Chem. Pharm. Bull 31 (1) 94 (1983); J.M. Cassal, A. Mariest, W.
  • heterocyclic compounds of general formula I have exceptional herbicidal properties.
  • the invention therefore also relates to herbicides
  • compositions containing an effective content of a compound of formula I and a carrier are advantageous
  • the invention also relates to a method for
  • Harmful plant control in which a herbicidally effective amount of a compound is applied to the harmful plants or their surroundings (before or after emergence)
  • Sprayable preparations can be stretched with suitable media and sprayed in quantities between a few and a few hundred liters per hectare. Highly concentrated preparations are mainly used as intermediates for other formulations.
  • the recipes contain, roughly speaking,
  • active ingredient (s) between 0.1 and 99% by weight of active ingredient (s) and at least one representative of group a) 0.1 to 20% of surface-active substances and b) approximately 1 to 99.9% of solid or liquid diluents. More specifically,
  • Active ingredient thinner active substances wetted powder 20 - 90 0 - 74 1 - 10
  • Active ingredient Thinner Active substances Aqueous suspensions 10 - 50 40 - 84 1 - 20
  • Active ingredients are sometimes desirable and are achieved by incorporating them into the recipe or by mixing in the container.
  • Granules and pellets can be produced by spraying the active ingredient onto preformed granular carriers or by agglomerating. See J.E. Browning, "Agglomeration", Chemical
  • the ingredients are mixed, roughly crushed in a hammer mill and then in a jet mill
  • a slurry of wettable powder with 25% solids is converted into a double-cone
  • the ingredients are mixed, ground in a hammer mill and then moistened with about 12% water.
  • the mixture is extruded into cylinders about 3 mm in diameter, which are cut into pellets about 3 mm in length. These can be used directly after drying; however, the dried pellets can be crushed so that the USS No. Pass through the 2C sieve (openings 0.84 mm diameter).
  • the on Granules remaining in the sieve USS No 40 (0.42 mm opening diameter) can be packaged for use while the fines are returned.
  • the active ingredient is dissolved in the solvent and the solution is sprayed onto dedusted granules in a double cone mixer. After the solution has been sprayed, the mixer is left to run for a short time, after which the granules are packaged.
  • Attapulgite clay 9% The ingredients are mixed and ground until they pass through a 100 mesh screen. This material is then fed to a fluid bed granulator, where the air flow is adjusted so that the material is easily whirled up and a fine jet of water is sprayed onto the whirled material. The fluidization and spraying are so long
  • desired size range usually 14 to 100 mesh (1410 to 149 ⁇ m), after which for the
  • the ingredients are mixed and ground together in a sand mill to create particles with
  • the ingredients are mixed and mixed in one
  • the ingredients are mixed and mixed in one
  • Example J Hammer mill ground to obtain particles substantially below 100 microns. The material is sieved through a USS No. 50 sieve and then packaged. Example J
  • the ingredients are mixed thoroughly, roughly ground in a hammer mill and then in one
  • the material is then mixed and packed again.
  • the ingredients are mixed and mixed in one
  • Example L Sand mill ground to obtain particles substantially below 5 microns in size.
  • the product can be used directly, stretched with oil or emulsified in water.
  • the active ingredient is mixed with attapulgite and then passed through a hammer mill to obtain particles substantially less than 200 microns.
  • the ground concentrate is then pulverized with the
  • the ingredients are ground together in a sand mill until the size of the solid particles is below about 5 microns, resulting thick suspension can be used directly, but is preferably used after stretching with oils or after emulsifying in water.
  • Biological examples
  • selective weed control in crops such as rice, wheat, barley, corn, soybeans, sugar beet and cotton.
  • the amount of the compounds according to the present invention to be applied depends on numerous factors, including the use as selective or universal herbicides, the particular crop, the type of weeds to be combated, the weather and climate, the selected recipe, the mode of application, the amount of leafy plants etc. In general, the compounds should be applied in amounts between 0.001 and 20 kg / ha, the lower amounts for lighter soils and / or soils
  • the compounds of the present invention can be used in combination with any other commercial herbicide.
  • the herbicidal properties of the compounds of the present invention have been found in a number of greenhouse experiments. The test methods and results are given below.
  • Seeds from digitaria spp, echinochloa crus-galli, setaria feberii, avena fatua, bromus secalinus, abutilon theophrasti, ipomoea spp., Xanthium pensylvanicum and sorghum tubers were placed and treated with the test chemicals dissolved in a non-phytotoxic solvent before germination.

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

Abstract

L'invention concerne des composés hétérocycliques. Les composés herbicides doivent agir à doses aussi faibles que possible en exerçant une haute sélectivité entre les plantes utiles et les mauvaises herbes. L'invention se propose de mettre au point de nouveaux composés chimiques pouvant être utilisés comme herbicides. Les nouveaux composés hétérocycliques ont la formule (I) dans laquelle X désigne O, S, CH2 ou CH2 substitué et Q désigne des benzols substitués. Ces composés peuvent être produits par exemple dans une formulation renfermant des substances tensioactives et des diluants solides ou liquides et utilisée afin de minimiser la croissance de végétation indésirable. L'invention concerne en outre des substances herbicides.
EP93917695A 1992-07-30 1993-07-29 Derives heterocycliques de pyrimidinedione et leur utilisation comme herbicides Withdrawn EP0652883A1 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE4225167 1992-07-30
DE4225167 1992-07-30
DE4225629 1992-08-03
DE4225629A DE4225629A1 (de) 1992-07-30 1992-08-03 Heterocyclische Verbindungen
PCT/EP1993/002027 WO1994003459A1 (fr) 1992-07-30 1993-07-29 Composes heterocycliques et leur utilisation comme herbicides

Publications (1)

Publication Number Publication Date
EP0652883A1 true EP0652883A1 (fr) 1995-05-17

Family

ID=25917054

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93917695A Withdrawn EP0652883A1 (fr) 1992-07-30 1993-07-29 Derives heterocycliques de pyrimidinedione et leur utilisation comme herbicides

Country Status (9)

Country Link
US (2) US5661107A (fr)
EP (1) EP0652883A1 (fr)
JP (1) JPH07509474A (fr)
CN (1) CN1085902A (fr)
AU (2) AU671476B2 (fr)
CA (1) CA2139585A1 (fr)
DE (1) DE4225629A1 (fr)
RU (1) RU95105602A (fr)
WO (1) WO1994003459A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4225629A1 (de) * 1992-07-30 1994-02-03 Degussa Heterocyclische Verbindungen
CN1202172A (zh) * 1995-10-25 1998-12-16 纳幕尔杜邦公司 具有除草作用的磺酰胺
CN108727367B (zh) * 2017-04-18 2021-01-05 山东先达农化股份有限公司 含吡啶并嘧啶二酮的苯并噁嗪酮类化合物及其制备方法和应用和除草剂组合物

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5888382A (ja) * 1981-11-24 1983-05-26 Ube Ind Ltd イミダゾピリミジン類の製法
US4725600A (en) * 1984-07-13 1988-02-16 Fujisawa Pharmaceutical Co., Ltd. Pyrimidine compounds having activity as a cardiotonic anti-hypertensive cerebrovascular vasodilator and anti-platelet aggregation agent
DE3788737T2 (de) * 1986-01-29 1994-05-05 Sumitomo Chemical Co Indazol-Verbindungen, Verfahren zu deren Herstellung, deren Anwendung und Zwischenprodukte.
EP0243734B1 (fr) * 1986-04-19 1991-07-17 MERCK PATENT GmbH Hydantoine optiquement active
GB8620060D0 (en) * 1986-08-18 1986-10-01 Roussel Lab Ltd Chemical compounds
DE3643748A1 (de) * 1986-12-20 1988-06-30 Hoechst Ag Bicylische imide, verfahren zu ihrer herstellung sowie ihre verwendung im pflanzenschutz
DE3712782A1 (de) * 1987-04-13 1988-11-03 Schering Ag Anellierte uracilderivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide mittel
US4927451A (en) * 1988-12-30 1990-05-22 Uniroyal Chemical Company, Inc. 3-aryldihydrouracils
US5270287A (en) * 1989-10-31 1993-12-14 Valent U.S.A. Corporation Method for defoliating and desiccating cotton
DE4225629A1 (de) * 1992-07-30 1994-02-03 Degussa Heterocyclische Verbindungen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9403459A1 *

Also Published As

Publication number Publication date
US5922647A (en) 1999-07-13
AU671476B2 (en) 1996-08-29
CA2139585A1 (fr) 1994-02-17
WO1994003459A1 (fr) 1994-02-17
AU4704393A (en) 1994-03-03
JPH07509474A (ja) 1995-10-19
AU671290B2 (en) 1996-08-22
RU95105602A (ru) 1997-05-10
CN1085902A (zh) 1994-04-27
DE4225629A1 (de) 1994-02-03
AU4704293A (en) 1994-03-03
US5661107A (en) 1997-08-26

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