WO1993012094A1 - Derives pyrimidinyl- ou triazinyl-oxy-(ou thio)-aldehydiques et leur utilisation comme herbicides ou regulateurs de la croissance des plantes - Google Patents

Derives pyrimidinyl- ou triazinyl-oxy-(ou thio)-aldehydiques et leur utilisation comme herbicides ou regulateurs de la croissance des plantes Download PDF

Info

Publication number
WO1993012094A1
WO1993012094A1 PCT/EP1992/002707 EP9202707W WO9312094A1 WO 1993012094 A1 WO1993012094 A1 WO 1993012094A1 EP 9202707 W EP9202707 W EP 9202707W WO 9312094 A1 WO9312094 A1 WO 9312094A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
phenyl
substituted
formula
hydrogen
Prior art date
Application number
PCT/EP1992/002707
Other languages
German (de)
English (en)
Inventor
Frank Zurmühlen
Klaus Bauer
Hermann Bieringer
Original Assignee
Hoechst Schering Agrevo 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 Hoechst Schering Agrevo Gmbh filed Critical Hoechst Schering Agrevo Gmbh
Priority to EP92923785A priority Critical patent/EP0618909A1/fr
Publication of WO1993012094A1 publication Critical patent/WO1993012094A1/fr

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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60—Three or more oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/30—Only oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6509—Six-membered rings
    • C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3

Definitions

  • the invention relates to compounds of the general formula (I)
  • R a , R b independently of one another hydrogen, alkyl, alkoxy, alkylthio,
  • X 1 , X 2 , X 3 and X 4 independently of one another O or S, preferably O, an aliphatic or araliphatic radical of the formula or
  • radicals are independently unsubstituted or mono- or polysubstituted by radicals from the group aikoxy, alkylthio, amino, alkylamino, dialkylamino, nitro, cyano, halogen, phenyl and substituted phenyl, or
  • Radical of the formula NR'R ", in which R 'and R" are independently of one another Are hydrogen, alkyl, benzyl or phenyl, or aminocarbonyl,
  • R 4 , R 5 independently of one another are hydrogen, alkyl, alkenyl, alkynyl,
  • R 4 and R 5 together with the connected N atom form a 3- to 7-membered heterocyclic ring which, in addition to the N atom, can contain further heteroatoms from the group N, O and S and are substituted by one or more alkyl groups or an oxo group can be,
  • R 6 , R 7 independently of one another are hydrogen, alkyl, alkenyl, alkynyl,
  • R 6 and R 7 together with the connected group -X 1 -CH-X 2 - a 4- to 8-membered heterocyclic ring which, in addition to the two heteroatoms, can contain further heteroatoms from the group N, O and S and by one or several alkyl groups can be substituted,
  • R 8 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, phenyl
  • R 9 , R 10 independently of one another are hydrogen, alkyl, alkenyl, alkynyl,
  • R 9 and R 10 together with the connected N atom form a 3- to 7-membered heterocyclic ring which, in addition to the N atom, can contain further heteroatoms from the group N, O and S and by one or several alkyl groups or one oxo group can be substituted, R 11 , R 12 independently of one another hydroxyl, alkyl, aikoxy, phenyl, substituted
  • R 13 is hydrogen or alkyl
  • R 14 is hydrogen, halogen, alkyl which is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, aikoxy, alkylthio, phenyl or substituted phenyl, or hydroxy, cyano, cycloalkyl, aryl, preferably phenyl, thienyl, naphthyl or Dihydronaphthyl, where aryl or cycloalkyl are unsubstituted or substituted,
  • R 15 , R 16 independently of one another are hydrogen or alkyl or
  • R 15 and R 16 together with the connected carbon atom form a 3- to 8-membered group
  • Ring which may contain an oxygen atom and which may be substituted by one or more alkyl groups,
  • R 17 is hydrogen or alkyl
  • R 18 is independently of R 19 is hydrogen or alkyl
  • R 19 is independently of R 18 alkyl, aryl or substituted aryl or
  • R 18 and R 19 together with the connected alkenylene group form a 3- to 8-membered ring which can contain an oxygen atom and can be substituted by one or more alkyl groups,
  • n is the number 0 or 1
  • alkyl, aikoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio radicals and the corresponding unsaturated and / or substituted radicals can each be straight-chain or branched. Unless specifically stated, the carbon atom chains for these radicals are or
  • Alkyl radicals also in the composite meanings ie aikoxy, haloalkyl etc., mean methyl, ethyl, n- or i-propyl, n-, i-, t- or 2- Butyl; Alkenyl and alkynyl radicals have the meaning of the alkyl radicals
  • haloalkyl means alkyl which is substituted by one or more atoms from the group halogen; Haloalkyl is, for example, CF 3 , CHF 2 , CH 2 CF 3 .
  • Aryl means, for example, phenyl, naphthyl,
  • Aryloxy means the corresponding aryl radicals which are bonded via an oxy group, preferably phenoxy.
  • Heteroaryl or heteroaryl in heteroaryloxy means, for example, pyridyl, pyrimidyl, pyridazyl, thienyl, furyl, pyrrolyl, pyrazolyl and imidazolyl, preferably pyridyl and thienyl, but also bicyclic or polycyclic aromatic or araliphatic compounds.
  • Substituted cycloalkyl means, for example, cycloalkyl which is substituted by radicals from the group alkyl and aikoxy.
  • Optionally substituted aryl, aryloxy, heteroaryl, heteroaryloxy, phenyl, phenoxy, benzyl and benzyloxy as well as bicyclic radicals with aromatic components preferably each represent the corresponding unsubstituted radical or represent a substituted radical derived therefrom, the substituents being for example one or more, preferably 1, 2 or 3 radicals from the group halogen, alkyl, haloalkyl, aikoxy, haloalkoxy, nitro, cyano, alkoxycarbonyl, alkylcarbonyl, alkanoyl, carbamoyl, mono- and dialkylaminocarbonyl, mono- and dialkylamino, alkylsulfinyl and
  • the invention also relates to all stereoisomers and their mixtures which are encompassed by formula (I) but are not specifically mentioned.
  • compounds of the formula (I) according to the invention in which Y is a nitrogen atom and Z is a nitrogen atom or a methine group.
  • R a , R b are independently hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, halogen, C 1 -C 4 haloalkoxy, C 1 -C 4 hafoalkyl , C 1 -C 4 alkylamino or di- (C 1 -C 4 -alkyl) amino, preferably methyl, methoxy, chlorine or methylamine, in particular one of the two methoxy radicals and the other radical methyl, methoxy, chlorine or methylamino
  • R 2 is hydrogen or tri- (C 1 -C 4 -alkyl) -silyI, preferably
  • R 3 C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy, C 2 -C 4 -
  • R 4 , R 5 independently of one another are hydrogen, C 1 -C 4 alkyl, C 2 -C 4 -
  • R 4 and R 5 together with the connected N atom form a 5- to 6-membered heterocyclic ring which, in addition to the N atom, has one or two more
  • R 6 , R 7 independently of one another are hydrogen, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -
  • R 6 and R 7 together with the connected group -X 1 -CH-X 2 - a 5- to 6-membered heterocyclic ring, which in addition to the two
  • Heteroatoms can contain a further heteroatom from the group N, O and S and can be substituted by one or more C 1 -C 4 alkyl groups,
  • R 8 is hydrogen, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 8 -
  • Cycloalkyl phenyl, substituted phenyl, benzyl, (C 1 -C 4 alkyl) carbonyl or benzoyl,
  • R 9 , R 10 independently of one another are hydrogen, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -
  • R 9 and R 10 together with the connected N atom form a 5- to 6-membered heterocyclic ring which, in addition to the N atom, has one or two more
  • Heteroatoms from the group N, O and S can contain and by one or more C 1 -C 4 alkyl groups and an oxo group can be substituted,
  • R 11 , R 12 independently of one another are hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, phenyl, substituted phenyl, phenoxy or substituted phenoxy,
  • R 13 is hydrogen or C 1 -C 4 -alkyl
  • R 14 is hydrogen, halogen, C 1 -C 4 alkyl which is unsubstituted or by
  • R 15 , R 16 independently of one another are hydrogen or C 1 -C 8 -alkyl or
  • Ring which may contain an oxygen atom and which may be substituted by one or more C 1 -C 4 alkyl groups,
  • R 17 is hydrogen or C 1 -C 4 alkyl
  • R 18 independently of R 19 is hydrogen or C 1 -C 4 alkyl
  • R 19 is independently of R 18 C 1 -C 4 alkyl, phenyl or substituted phenyl or
  • R 18 and R 19 together with the connected alkenylene group form a 5- or 6-membered ring which may contain an oxygen atom and which may be substituted by one or more C 1 -C 4 -alkyl groups, M + sodium or potassium cation and
  • n is the number 0 or 1, preferably 0,
  • Preferred compounds of the formula (I) according to the invention are those in which
  • R 2 is hydrogen or tri (C 1 -C 2 alkyl) silyl, preferably hydrogen
  • Trimethylsilyl or triethylsilyl in particular hydrogen, R 3 C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, the latter two radicals independently of one another unsubstituted or halogenated once or more or by C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, amino, (C 1 -C 4 -alkyl) -amino, di- (C 1 -C 4 alkyl) amino, nitro, cyano, phenyl and substituted phenyl are substituted, or
  • R 4 , R 5 independently of one another are hydrogen, C 1 -C 4 alkyl, cyclopentyl,
  • R 4 and R 5 together with the connected N atom form a 5- or 6-membered heterocyclic ring which, in addition to the N atom, is another
  • R 6 , R 7 independently of one another are hydrogen, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -
  • R 6 and R 7 together with the connected group -X 1 -CH-X 2 - a 5- to 6-membered heterocyclic ring which can be substituted by one or more methyl groups,
  • R 8 is hydrogen, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, cyclopentyl,
  • R 9 , R 10 independently of one another are hydrogen, C 1 -C 4 -alkyl, cyclopentyl,
  • R 9 and R 10 together with the connected N atom have a 5- to 6-membered heterocyclic ring, which is another in addition to the N atom
  • R 11 , R 12 independently of one another are hydroxy, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, phenyl, substituted phenyl, phenoxy or substituted phenoxy and
  • R 13 is hydrogen or C 1 -C 2 alkyl
  • R 1 is an aliphatic or araliphatic radical of the formula
  • R 14 is hydrogen, halogen, C 1 -C 6 alkyl which is unsubstituted or by.
  • R 15 , R 16 independently of one another are hydrogen or C 1 -C 4 -alkyl or
  • R 15 and R 16 together with the connected carbon atom have a 5- or 6-membered group
  • Ring which may contain an oxygen atom and which may be substituted by one or more C 1 -C 4 -alkyl groups,
  • R 1 particularly preferably denotes C 1 -C 4 -alkyl which is unsubstituted or substituted by methoxy or phenyl, or C 3 -C 6 -cycloalkyl which is unsubstituted or substituted by one to three methyl groups, in particular isopropyl, tert-butyl or Cyclopentyl.
  • A denotes a radical of the formula (A1) or (A2) mentioned.
  • Another object of the present invention is the method for
  • R a , R b , X, Y, Z and R 1 as in formula (I) are defined and Nuf 2 for a nucleofugic leaving group, e.g. B. from the group consisting of halogen, alkylsulfonyl and benzylsulfonyl, or c) a compound of formula (VI),
  • R a , R b , X, Y, Z and R 1 are as defined in formula (I),
  • Reaction conditions can be easily converted into it.
  • the reactions of variants a) and b) are preferably carried out in the presence of an inorganic or organic base.
  • bases therefor are, for example, inorganic bases from the group of alkali metal carbonates, such as Na 2 CO 3 , K 2 CO 3 , NaHCO 3 or KHCO 3 , alkali and alkaline earth metal hydrides such as NaH and KH, alkali metals such as sodium and potassium, and alkali metal hydroxides, how
  • Sodium hydroxide and potassium hydroxide, or organic bases such as triethylamine or DBU (1,8-diazabicyclo [5.4.0] undec-7-en) are suitable.
  • Methanol, ethanol and isopropanol, or ether such as.
  • diethyl ether diglyme, monoglyme, tetrahydrofuran and dioxane, or ketones, such as. B. acetone and methyl ethyl ketone, or esters such as ethyl acetate, or other aprotic polar
  • Solvents such as dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide and acetonitrile, or else water and mixtures of two or more of the solvents mentioned.
  • the reactions of variants c 1) to c 8) can be prepared analogously to conventional methods for reaction of aldehydes with nucleophiles and acetal preparation, for example, without a catalyst or under basic or acidic catalysis, are preferably carried out usually under weakly 'acidic conditions.
  • the two-stage Reaction according to c 4 ) can be carried out according to or analogously to the process for the preparation of mixed acetals, e.g. B. according to Chem. Ber. 103 (1970) 3918 ff.
  • the compounds of the formulas (VI) are new and also a subject of the invention.
  • the compounds of formula (I) according to the invention have excellent herbicidal activity against a broad spectrum of economically important mono- and dicotyledonous harmful plants. Also difficult to fight perennials
  • dicotyledon weed species the spectrum of activity extends to species such as Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea,
  • the substances according to the invention have excellent growth-regulating properties in crop plants. You grab regulate the plant's own metabolism and can thus be used to specifically influence plant ingredients and to facilitate harvesting, such as by triggering desiccation and stunted growth. Furthermore, they are also suitable for general control and inhibition of undesired vegetative growth without killing the plants. Inhibiting vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, as this can reduce or completely prevent gas storage.
  • the compounds of the formula (I) according to the invention can be used in the customary formulations, for example in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules.
  • the invention therefore also relates to herbicides and
  • Formulation components usually require systematic test series.
  • formulation types are wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions,
  • SC Suspension concentrates
  • CS capsule suspensions
  • DP dusts
  • pickling agents granules for spreading and soil application
  • granules GR
  • WG water-dispersible granules
  • SG water-soluble granules
  • Solvents and other additives are also known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluent and Carriers", 2nd Ed., Darland Books, Caldwell NJ, Hv Olphen, "Introduction to Clay Colloid Chemistry”; 2nd Ed., J Wiley & Sons, NY; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, NY 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ; Sisley and Wood, ⁇ ncyclopedia of Surface Active Agents ", Chem. Publ. Co. Inc., NY 1964; Schoenfeldt,
  • Manufacture fungicides, safeners, fertilizers and / or growth regulators e.g. in the form of a finished formulation or as a tank mix.
  • Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain not only a diluent or inert substance, but also ionic and / or nonionic surfactants (wetting agents, dispersing agents), e.g. polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines,
  • the herbicidal active ingredients are finely ground, for example in conventional apparatus such as hammer mills, fan mills and air jet mills, and simultaneously or subsequently with the
  • Formulation aids mixed.
  • Emulsifiable concentrates are obtained by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or even higher-boiling aromatics or hydrocarbons or mixtures the organic solvent with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
  • organic solvent for example butanol, cyclohexanone, dimethylformamide, xylene or even higher-boiling aromatics or hydrocarbons or mixtures the organic solvent with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
  • emulsifiers alkylarylsulfonic acid calcium salts such as Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as
  • Fatty acid polyglycol esters alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as, for. B. sorbitan fatty acid esters or polyoxethylene sorbitan esters such. B.
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solid substances e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates can be water or oil based. You can, for example, by wet grinding using commercially available bead mills and optionally adding surfactants, such as z. B. above with the others
  • Emulsions e.g. B. oil-in-water emulsions (EW) can be, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants such as z. B. are already listed above for the other types of formulation.
  • Granules can either by spraying the active ingredient
  • Carriers such as sand, kaolinite or granulated inert material. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers.
  • Water-dispersible granules are generally produced using the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • spray drying fluidized bed granulation
  • plate granulation mixing with high-speed mixers and extrusion without solid inert material.
  • spray granules see, for example, the process in "Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London; JE Browning, "Agglomeration”, Chemical and Engineering 1967, pages 147 ff; "Perry's Chemical Engineer's Handbook," 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.
  • the agrochemical preparations usually contain 0.1 to 99
  • the active substance concentration in wettable powders is e.g. about 10 to 90 wt .-%, the rest of 100 wt .-% consists of conventional formulation components.
  • the active substance concentration can be about 1 to 90, preferably 5 to 80,% by weight.
  • Dust-like formulations contain 1 to 30, preferably mostly 5 to 20% by weight of active ingredient, sprayable
  • Water-dispersible granules the active ingredient content depends in part on whether the active compound is liquid or solid and which granulation aids, fillers, etc. are used.
  • the active ingredient content of the water-dispersible granules is, for example, between 1 and 95% by weight,
  • the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreezes and solvents, fillers, carriers and dyes, defoamers,
  • Combination partners for the active substances according to the invention can be used, for example, known active substances, such as those found in e.g. from Weed Research 26, 441-445 (1986), or "The Pesticide Manual", 9th edition, The British Crop Protection Council, 1990/91, Bracknell, England, and the literature cited therein.
  • herbicides known from the literature which can be combined with the compounds of formula (I), z.
  • active substances to name the following active substances (Note: The
  • bromac ⁇ l bromobutide; bromofenoxim; bromoxynil; bromuron; buminafos;
  • busoxinone butachlor; butamifos; butenachlor; buthidazole; butralin; butylates;
  • CDAA i.e. H. 2-chloro-N, N-di-2-propenylacetamide
  • CDEC i.e. H.
  • chlomethoxyfen chloramben; chlorazifop-butyl, pirifenop-butyl; chlorbromuron;
  • chlororthal dimethyl chlorothiamide; cinmethylin; cinosulfuron; clethodim; clomazone; clomeprop; cloproxydim; clopyralid; cyanazine; cycloate; cycloxydim; cycluron;
  • fluorodifen fluoroglycofen-ethyl; fluridone; flurochloridone; fluroxypyr; flurtamone; fomesafen; fosamine; furyloxyfen; glufosinate; glyphosate; halosates; haloxyfop and its ester derivatives; hexazinone; Hw 52, d. H. N- (2,3-dichlorophenyl) -4- (ethoxymethoxy) benzamide; imazamethabenz-methyl; imazapyr; imazaquin;
  • met.zthiazuron metham; methazole; methoxyphenone; methyldymron;
  • nitrofluorfen norflurazon; orbencarb; oryzalin; oxadiazon; oxyfluorfen; paraquat; pebulate; pendimethalin; perfluidone; phenmedipham; phenisopham;
  • phenmedipham phenmedipham; picloram; piperophos; piributicarb; pirifenop-butyl; pretilachlor; primisulfuron-methyl; procyazine; prodiamine; profluralin; proglinazine-ethyl;
  • prometon prometryn; propachlor; propanil; propaquizafop and its
  • prynachlor pyrazolinates; pyrazone; pyrazosulfuron-ethyl; pyrazoxyfen; pyridate;
  • terbumeton terbuthylazine; terbutryn; TFH 450, i.e. H. N, N-Diethyl-3 - [(2-ethyl-6-methylphenyl) sulfonyl] -1H-1,2,4-triazole-1-carboxamide; thiazafluron;
  • thifensulfuron-methyl thifensulfuron-methyl
  • thiobencarb tiocarbazil
  • tralkoxydim tri-allate; triasulfuron; triazofenamide; tribenuron-methyl; triciopyr; tridiphane; trietazine; trifluralin;
  • the formulations present in the commercial form are optionally diluted in the usual manner, e.g. for spray powders, emulsifiable concentrates, dispersions and water-dispersible granules using water. Preparations in the form of dust, ground granules or scattering granules and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the compounds of the formula (I) are applied, for. B. in the post-emergence process by overhead application to the plants,
  • the compounds according to the invention can be carried out in the presence of crop plants.
  • the lances mean the crop plants or the soil the area under cultivation.
  • a dusting agent is obtained by mixing 10 parts by weight of a compound of the formula (I) and 90 parts by weight of talc as an inert substance and in a
  • Wettable powder is obtained by mixing 25 parts by weight of a compound of formula (I), 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyl taurine as a wetting and dispersing agent and grinding in a pin mill.
  • a dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of a compound of the formula (I) with 6 parts by weight
  • Alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight
  • Isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range e.g. approx. 255 to above 277 ° C) are mixed and ground in a grinder mill to a fineness of less than 5 microns.
  • a water-dispersible granulate is obtained by:
  • Seeds or rhizome pieces of monocotyledonous and dicotyledonous weed plants were placed in sandy loam in plastic pots and covered with soil.
  • Formulated in the form of wettable powders or emulsion concentrates were placed in sandy loam in plastic pots and covered with soil.
  • Compounds according to the invention have a good herbicidal pre-emergence activity against a broad spectrum of grasses and weeds.
  • the compounds (Ia) of Examples 1 and 11 from Table 1 the compounds (Ib) of Examples 25, 29, 37, 41, 49, 53 and 61 from Table 2 and the compounds (Ic) of Examples 1 and 5 from Table 3 very good herbicidal activity against harmful plants such as Sinapis alba, Stellaria media, Echinochloa crus-galli, Lolium multiflorum and Avena fatua in the pre-emergence process.
  • the compounds according to the invention formulated as wettable powder or as emulsion concentrates were mixed in different doses with a
  • Agents according to the invention have good herbicidal properties even after emergence
  • the compounds (Ia) of Examples 1 and 11 from Table 1 very good herbicidal activity against harmful plants such as Sinapis alba, Stellaria media,
  • Echinochloa crus-galli Lolium multiflorum and Avena fatua in the post-emergence process.

Landscapes

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

Abstract

Il est connu que des dérivés d'acide pyrimidinyloxy(thio)- et triazinyloxy(thio)-carboxylique présentent des propriétés herbicides et régulatrices de la croissance des plantes. Les matières actives connues des structures de ce type présentent toutefois partiellement des inconvénients au cours de leur utilisation, tels que, par exemple, une sélectivité insuffisante dans les cultures utiles importantes. L'invention a pour objet des dérivés pyrimidinyloxy(thio)- et triazinyloxy(thio)-aldéhydiques présentant des propriétés herbicides avantageuses, de formule (I) dans laquelle X, Y, Z, A, Ra et Rb sont tels que définis dans la revendication 1.
PCT/EP1992/002707 1991-12-10 1992-11-25 Derives pyrimidinyl- ou triazinyl-oxy-(ou thio)-aldehydiques et leur utilisation comme herbicides ou regulateurs de la croissance des plantes WO1993012094A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP92923785A EP0618909A1 (fr) 1991-12-10 1992-11-25 Derives pyrimidinyl- ou triazinyl-oxy-(ou thio)-aldehydiques et leur utilisation comme herbicides ou regulateurs de la croissance des plantes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4140717.2 1991-12-10
DE4140717 1991-12-10

Publications (1)

Publication Number Publication Date
WO1993012094A1 true WO1993012094A1 (fr) 1993-06-24

Family

ID=6446725

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1992/002707 WO1993012094A1 (fr) 1991-12-10 1992-11-25 Derives pyrimidinyl- ou triazinyl-oxy-(ou thio)-aldehydiques et leur utilisation comme herbicides ou regulateurs de la croissance des plantes

Country Status (4)

Country Link
EP (1) EP0618909A1 (fr)
AU (1) AU2945392A (fr)
CA (1) CA2125570A1 (fr)
WO (1) WO1993012094A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0630890A2 (fr) * 1993-06-24 1994-12-28 Nihon Bayer Agrochem K.K. Dérivés de pyrimidine
US5969134A (en) * 1994-10-14 1999-10-19 Basf Aktiengesellschaft Carboxylic acid derivatives, their preparation and use
US11426412B2 (en) 2017-10-18 2022-08-30 Jubilant Epipad LLC Imidazo-pyridine compounds as PAD inhibitors
US11459338B2 (en) 2017-11-24 2022-10-04 Jubilant Episcribe Llc Heterocyclic compounds as PRMT5 inhibitors
US11529341B2 (en) 2018-03-13 2022-12-20 Jubilant Prodel LLC Bicyclic compounds as inhibitors of PD1/PD-L1 interaction/activation
US11629135B2 (en) 2017-11-06 2023-04-18 Jubilant Prodell Llc Pyrimidine derivatives as inhibitors of PD1/PD-L1 activation
US11833156B2 (en) 2017-09-22 2023-12-05 Jubilant Epipad LLC Heterocyclic compounds as pad inhibitors

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0400741A1 (fr) * 1989-06-02 1990-12-05 Shell Internationale Researchmaatschappij B.V. Composés à activité herbicide

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0400741A1 (fr) * 1989-06-02 1990-12-05 Shell Internationale Researchmaatschappij B.V. Composés à activité herbicide

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0630890A2 (fr) * 1993-06-24 1994-12-28 Nihon Bayer Agrochem K.K. Dérivés de pyrimidine
EP0630890A3 (fr) * 1993-06-24 1995-01-11 Nihon Bayer Agrochem K.K. Dérivés de pyrimidine
US5969134A (en) * 1994-10-14 1999-10-19 Basf Aktiengesellschaft Carboxylic acid derivatives, their preparation and use
US11833156B2 (en) 2017-09-22 2023-12-05 Jubilant Epipad LLC Heterocyclic compounds as pad inhibitors
US11426412B2 (en) 2017-10-18 2022-08-30 Jubilant Epipad LLC Imidazo-pyridine compounds as PAD inhibitors
US11629135B2 (en) 2017-11-06 2023-04-18 Jubilant Prodell Llc Pyrimidine derivatives as inhibitors of PD1/PD-L1 activation
US11459338B2 (en) 2017-11-24 2022-10-04 Jubilant Episcribe Llc Heterocyclic compounds as PRMT5 inhibitors
US11529341B2 (en) 2018-03-13 2022-12-20 Jubilant Prodel LLC Bicyclic compounds as inhibitors of PD1/PD-L1 interaction/activation

Also Published As

Publication number Publication date
CA2125570A1 (fr) 1993-06-24
AU2945392A (en) 1993-07-19
EP0618909A1 (fr) 1994-10-12

Similar Documents

Publication Publication Date Title
EP0757679B1 (fr) Aminophenylsulfonylurees acylees, leur procede de preparation et leur utilisation comme herbicides ou comme regulateurs de croissance pour vegetaux
EP0574418B1 (fr) Arylsulfonylurees, leur procede de production et leur utilisation comme herbicides et regulateurs de la croissance
EP0706518B1 (fr) Aminophenyl-urees acylees, leur preparation et leur application comme herbicides et comme regulateurs de croissance vegetale
DE4335297A1 (de) Phenylsulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
EP0666852B1 (fr) Nouvelles phenylsulfonylurees, leur preparation et leur utilisation comme herbicides et comme regulateurs de croissance vegetale
DE4230933A1 (de) Hydroxylamino-phenylsulfonylharnstoffe, Darstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren
WO1995032951A1 (fr) Urees de phenylsulfonyle comportant des substituants d'azote, leurs procedes de preparation et leur utilisation comme herbicides et comme regulateurs de croissance pour vegetaux
WO1993012094A1 (fr) Derives pyrimidinyl- ou triazinyl-oxy-(ou thio)-aldehydiques et leur utilisation comme herbicides ou regulateurs de la croissance des plantes
EP0555770A1 (fr) N-Hétéroaryl-N'-(pyrid-2-yl-sulfonyl)-urées, procédé pour leur préparation et leur usage comme herbicides et régulateurs de croissance des plantes
EP0763028B1 (fr) Formylaminophenylsulfonylurees, leur procede de fabrication et leur utilisation en tant qu'herbicides et regulateurs de croissance des vegetaux
EP0541041A1 (fr) Dérivés d'acides pyrimidinyl- ou triazinyloxy-(ou -thio)-carboxyliques, procédé pour leur préparation et l'usage comme herbicides ou régulateurs de croissance des plantes
WO1994013619A1 (fr) Benzoylcyclohexenones, leur procede de preparation et leur utilisation comme herbicides et regulateurs de croissance des vegetaux
EP0715629B1 (fr) N-heteroaryl-n'-(pyrid-2-yl-sulfonyl)urees, leur procede de preparation et leur utilisation comme herbicides et regulateurs de croissance vegetale
DE4439676A1 (de) Schwefelsubstituierte Phenylsulfonylharnstoffe, Verfahren zu deren Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DE4304288A1 (de) Thienylsulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
EP0863707B1 (fr) 5-acylamino-2-alcoxycarbonylphenylsulfonylurees utilisees comme herbicides selectifs
EP0562510A1 (fr) Dérivés optiquement actifs d'acides carboxyliques substitués par des groupes pyrimidinyl- ou triazinyloxy-(ou -thio), procédé pour leur préparation et leur usage comme herbicide et régulateurs de croissance de plantes
WO1995006039A1 (fr) Nouveaux derives d'acide phenylglyoxylique, leurs procedes de preparation et leur utilisation comme herbicides et comme regulateurs de croissance vegetale
DE4324060A1 (de) N-Heteroaryl-N'-(pyrid-2-yl-sulfonyl)-harnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DE4311787A1 (de) Fluormethylsulfonyl-substituierte Pyridylsulfonylharnstoffe als Herbizide, Verfahren zu ihrer Herstellung und ihre Verwendung
DE19510078A1 (de) Formylaminophenylsulfonylharnstoffe, Verfahren zur Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DE4335587A1 (de) N-Heteroaryl-N'-(pyrid-2-yl-sulfonyl)-Harn- stoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DE4330893A1 (de) N-Heteroaryl-N'(pyrid-2-yl-sulfonyl)-harnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DE4328397A1 (de) N-Heteroaryl-N'(pyrid-2-yl-sulfonyl)-harnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU CA JP 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

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
WWE Wipo information: entry into national phase

Ref document number: 1992923785

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 2125570

Country of ref document: CA

ENP Entry into the national phase

Ref document number: 1994 244606

Country of ref document: US

Date of ref document: 19940711

Kind code of ref document: A

WWP Wipo information: published in national office

Ref document number: 1992923785

Country of ref document: EP

WWW Wipo information: withdrawn in national office

Ref document number: 1992923785

Country of ref document: EP