EP0738271A1 - Derives de l'acide phosphonique contenant un cycle triazole, utilises en tant qu'herbicides - Google Patents

Derives de l'acide phosphonique contenant un cycle triazole, utilises en tant qu'herbicides

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Publication number
EP0738271A1
EP0738271A1 EP95903443A EP95903443A EP0738271A1 EP 0738271 A1 EP0738271 A1 EP 0738271A1 EP 95903443 A EP95903443 A EP 95903443A EP 95903443 A EP95903443 A EP 95903443A EP 0738271 A1 EP0738271 A1 EP 0738271A1
Authority
EP
European Patent Office
Prior art keywords
formula
alkyl
hydrogen
compound
alkoxy
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Withdrawn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
EP95903443A
Other languages
German (de)
English (en)
Inventor
Ichiro Mori
Yoko Kimura
Shinichiro Matsunaga
Toshihito Nakano
Anthony Cornelius O'sullivan
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.)
Japat AG
Original Assignee
Japat 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
Priority claimed from GB9400178A external-priority patent/GB9400178D0/en
Priority claimed from GB9407233A external-priority patent/GB9407233D0/en
Application filed by Japat AG filed Critical Japat AG
Publication of EP0738271A1 publication Critical patent/EP0738271A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing heterocyclic radicals
    • 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
    • C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
    • C07F9/6518—Five-membered rings
    • 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
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom

Definitions

  • the present invention relates to novel triazoles which have a herbicidal action and are plant-growth-inhibiting, to processes for their preparation, to compositions containing them as active substances, and to their use for controlling weeds, especially selectively in crops, or for inhibiting plant growth.
  • Triazole compounds which have a herbicidal action are generally known.
  • WO 93/15610 and US-A-5,248,655 describe herbicidally active triazole compounds.
  • compounds of the formula (I) have a herbicidal and plant-growth-inhibiting action. They are therefore suitable as active substances in weed killers and in compositions for inhibiting plant-growth.
  • the triazoles according to the invention are those of the formula I
  • A is hydrogen, Cj-C -alkyl, C 2 -C 4 -alkenyl, triphenylmethyl, benzyl, a
  • Rj is hydrogen, C r C 6 -alkyl, OR 19 or NR 20 R 21 ;
  • R 2 is hydrogen, C r C 6 -alkyl, OR 19 or NR 20 R 21 , or R 2 and R 2 together form an oxo group;
  • R 3 is hydrogen, C r C 6 -alkyl, C r C 6 -alkoxy or represents together with R a chemical bond;
  • R 4 is hydrogen, C r C 4 -alkyl, C r C 4 -alkyl substituted by halogen, cyano, COOH,
  • C r C 4 -alkoxycarbonyl amino, di(C r C 4 )-alkylamino, C 1 -C 4 -alkylamino, phenyl, benzyl or an alkali metal, alkaline earth metal, ammonium, mono-, bis- or tris-C 1 -C 6 -alkylammonium, trialkylsulphonium, trialkylsulfoxonium, phosphonium or amidinium cation;
  • X is oxygen, S(O) m , NR 5 or CR 6 R 7 ;
  • Y is oxygen, S(O) p , NR 5 or CR ⁇ ;
  • Z is oxygen, S(O) q , NR 5 or CR 10 n;
  • m, p and q are each independently of the others 0, 1 or 2;
  • R 5 is hydrogen, C- j -Cg-alkyl which is unsubstituted or substituted by halogen, C
  • R 6 , R 7 , R 8 , R 9 , R 10 and R n are each independently of the others hydrogen, C r C 6 -alkyl which is unsubstituted or substituted by hydroxy, amino, C r C 4 -alkoxy, C 1 -C 4 -alkylamino or phenyl, which itself is unsubstituted or substituted by ⁇ -alkyl, halogen, C 1 -C 4 -haloalkyl, ⁇ -alkoxy, cyano, nitro, C r C 4 -alkylthio, C 1 -C 4 -alkylsulf ⁇ nyl, C 1 -C 4 -alkylsulfonyl or C 1 -C -alkoxycarbonyl; phenyl, benzyl which are unsubstituted or substituted by C j ⁇ -alkyl, halogen, C 1 -C -haloalkyl, C r
  • R 12 is hydrogen, a group or a group
  • R 13 is hydrogen, C---C 6 -alkyl, C r C 6 -alkoxy, hydroxy, C r C 6 -alkylcarbonyl, C- ⁇ -C 6 -alkoxycarbonyl, benzoyl which is unsubstituted or substituted by C r C 4 -alkyl, halogen, C r C 4 -haloalkyl, C-i ⁇ -alkoxy, cyano, nitro, C 1 -C 4 -alkylthio,
  • C 1 -C 4 -alkoxycarbonyl phenyl or by phenyl which itself is substituted by C 1 -C 4 -alkyl, halogen, C j ⁇ -haloalkyl, C- f Q ⁇ -alkoxy, cyano, nitro, C r C 4 -alkylthio, C 1 -C 4 -alkylsulf ⁇ nyl, C 1 -C 4 -alkylsulfonyl or C r C 4 -alkoxycarbonyl;
  • R 14 is hydrogen or Cj-C ⁇ -alkyl;
  • R 15 is C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl; or C r C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl substituted by halogen or C 1 -C 4 -alkoxy; or phenyl, benzyl; or phenyl, benzyl substituted by C r C 4 -alkyl, halogen, halomethyl, C r C 4 -alkoxy, cyano, nitro, C 1 -C 4 -alkoxycarbonyl, C r C 4 -alkylthio, C 1 -C -alkylsulfinyl or C C -alkylsulfonyl; R 16 is C r C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6
  • R 19 is hydrogen, a group
  • Q is oxygen or sulfur
  • R 2 o is hydrogen, C r C 6 -alkyl, C r C 6 -alkoxy, hydroxy, Cj- -alkylcarbonyl, Cj- -alkoxycarbonyl, benzoyl which is unsubstituted or substituted by C r C 4 -alkyl, halogen, C r C 4 -haloalkyl, C r C 4 -alkoxy, cyano, nitro, C r C 4 -alkylthio, C r C 4 -alkylsulf ⁇ nyl, C 1 -C 4 -alkylsulfonyl or C r C -alkoxycarbonyl; a group
  • C r C -alkoxycarbonyl phenyl or by phenyl which itself is substituted by C r C 4 -alkyl, halogen, C j ⁇ -haloalkyl, C 1 -C 4 -alkoxy, cyano, nitro, C r C 4 -alkylthio, C 1 -C -alkylsulfinyl, C r C 4 -alkylsulfonyl or C 1 -C 4 -alkoxycarbonyl;
  • R 21 is hydrogen or C j -Cg-alkyl;
  • R 22 is hydrogen, C r C -alkyl, C r C 4 -alkyl substituted by halogen, cyano, COOH, C r C 4 -alkoxycarbonyl, amino, di(C C 4 )-alkylamino, C r C 4 -alkylamino, phenyl, benzyl or an alkali metal, alkaline earth metal, ammonium, mono-, bis- or tris-alkylammonium, trialkylsulphonium, trialkylsulfoxonium, phosphonium or amidinium cation;
  • R- 23 is C r C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl; or C r C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl substituted by halogen or ⁇ -alkoxy; or phenyl
  • R 25 is hydrogen or C 1 -C 6 -alkyl
  • R 26 is hydrogen or C j -Cg-alkyl, with the proviso that a) at least two of the substituents X, Y and Z are carbon atoms, b) that R_ or R 2 is OR 1 or NR 20 R 21 if simultaneously X, Y and Z are carbon atoms and Qj is OR 12 and c) that Rj and R 2 are not simultaneously OR 19 , NR 20 R 2 ⁇ or both of them.
  • halogen is to be understood as being fluorine, chlorine, bromine and iodine, preferably fluorine, chlorine and bromine.
  • Alkyl is, for example, methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, sec -butyl, tert-butyl and the various isomeric pentyl or hexyl radicals.
  • Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl and 2,2,2-trichloroethyl.
  • Alkoxy is, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy; preferably methoxy.
  • Alkenyl is to be understood as being straight-chain or branched alkenyl, for example vinyl, allyl, methallyl, 1 -methyl vinyl, but-2-en-l-yl, 3-pentenyl, 2-hexenyl or 3-heptenyl.
  • Alkenyl radicals having a chain length of 2 or 3 carbon atoms are preferred.
  • alkynyl radicals occurring in the definitions of the substituents may be straight-chained or branched, for example ethynyl, propargyl, 3-butynyl, 1-methylpropargyl, 2-pentynyl or 2-hexynyl. Ethynyl and propargyl are preferred.
  • Alkoxycarbonyl is, for example: methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl and n-butoxycarbonyl, preferably methoxycarbonyl and ethoxy ⁇ carbonyl.
  • the formula I therefore also embraces all stereoisomers which are possible and which are in the form of enantiomers, diastereomers or their mixtures.
  • organic ammonium cation is intended to include ammonium cations prepared from low molecular weight amines, that is to say those having a molecular weight below about 300.
  • amines include alkylamines, alkenylamines, and alkanolamines containing not more than two amino groups, such as methylamine, ethylamine, n-propylamine, iso-propylamine, the four isomeric butylamines, n-amylamine, iso-amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methyl-ethylamine, methyl-isopropylamine, methyl-hexylamine, methyl-nonylamine, methyl-pen ta
  • Tetra-substituted ammonium cations are also included, for example tetramethylammonium, tetrabutylammonium, benzyltrimethylammonium, benzyltriethylammonium, tetra-ethylammonium and trimethylethylammonium cations.
  • Trialkylsulfonium cations include those, for example, in which each of the three alkyl groups, which are not necessary all the same, may contain from 1 to 6 carbon atoms.
  • Trialkylsulfoxonium cations likewise include those in which each of the three alkyl groups, which may be the same or different, may contain from 1 to 6 carbon atoms.
  • Phosphonium cations include, for example, cations in which the phosphorus atom bears four substituents, each of which may be an alkyl group of one to ten carbon atoms or a phenyl group, for example, the tetramethylphosphonium, tetrabutylphosphonium, and tetraphenylphosphonium cations.
  • DBU l,5-Diazabicyclo[5.4.0]undec-5-ene
  • Alkali metal cations include lithium, sodium and potassium; and alkaline earth metal cations include magnesium, calcium, strontium and barium.
  • Preferred compounds of the formula I are those, in which A is hydrogen.
  • Preferred compounds of the formula I which must be emphasised are those in which Q j is hydroxy or amino. Further preferred compounds of the formula I are those in which R ⁇ , R 2 , R 3 , R 4 and R 22 are hydrogen.
  • compounds of the formula I which are of particular interest are those in which X is CRgR-;, Y is CRgR-j and Z is NR 5 .
  • Further preferred compounds from amongst those of the formula I are those in which Qj is hydroxy and A, R 4 , R 6 , R 7 , R 8 , R 9 and R 2 are hydrogen.
  • a preferred individual compound from the scope of formula I is 2-Oxa-3-hydroxy-3-(l,2,4-triazol-3-yl)-cyclohexane phosphonic acid.
  • Preferred compounds of the formula I which are of particular interest are those, in which
  • a further subject of the present invention is a process for the preparation of compounds of the formula I which comprises a) for the preparation of a compound of the formula I, in which Q_ is hydroxy, reacting a compound of the formula II
  • R 1; R 2 , R 3 , X, Y and Z have the meanings given for formula I and A
  • R 4 and R 22 have the meanings given for formula I except for hydrogen, and optionally cleaving protecting groups A and/or R and R 22 and further converting them into a salt
  • R 12 is a group and A, R l5 R 2 , R 3 , R 4 , R 15 ,
  • R 16 , R 22 , X, Y and Z have the meanings given for formula I, reacting a compound of the formula IV
  • R-., R , R 3 , X, Y and Z have the meanings given for formula I and A
  • R 4 and R 2 have the meanings given for formula I except for hydrogen, in the presence of NaN 3 and CF 3 COOH to the corresponding azide and subsequently reducing the azide
  • Z Q is a leaving group, for example halogen, preferably chlorine, and Q 0 is for H 3 C, CH 3
  • R 13 and R 1 are as defined under formula I, and optionally cleaving the groups R and R 22 , for example with trimethylsilyl bromide and a solvent, for example dichlormethane, followed by treatment with an alcohol and propylene oxide, and further converting them into a salt,
  • A has the meanings given for formula I except for hydrogen and M is Sodium, Magnesium, Lithium, Cerium or Copper, with a compound of the formula
  • R-* , R 2 , R 3 , R 13 , X, Y and Z have the meanings given for formula I and R 4 and R 22 have the meanings given for formula I except for hydrogen in the presence of an inert solvent, or
  • R 3 , R 4 , R 2 , X, Y and Z have the meanings given for formula I and R 13 and R 14 have the meanings given above and converting said compound in the presence of sodium methylate and formyl hydrazine to the compound of the formula I.
  • Process a) is carried out in a manner or analogously as given by A.R. Katritzky, Tetrahedron 46 (1990), page 641 ff.
  • the protecting group A as triphenylmethyl, benzyl, a
  • Processes b), c), e) and f) are carried out in a manner or analogously as given in Chem. Rev. 1953, 52, pages 237 - 416 (b); D. Baldermann, Organic Synthesis 1981, 60, 104 (c); E. Ciganek, J. Org. Chem. 1992, 57, 4521; F.A. Davis, J. Org. Chem. 1977, 42, 398 and B. Lipschutz, Tetrahedron 1986, 27, 4241 (d) and S.L. Crooks, J. Med. Chem. 1986, 29, 1988 and T. Murakami, Heterocycles 1981, 15, 301 (e).
  • the meaning chlorine is preferred for the substituents X ! and X 2 .
  • R 4 and R 2 have the meanings given for formula I except for hydrogen, in an inert solvent, preferably dichloromethane, in the presence of N,O-bis(trimethylsilyl)acetamide and trimethylsilyl trifluoromethanesulfonate at temperatures of from -78°C to 40°C, preferably -20°C to 20°C, or
  • R 4 and R 22 have the meanings given for formula I except for hydrogen and R 28 is methyl or tert. -butyl, in an inert solvent, preferably dichloromethane, in the presence of a compound of the formula XV
  • R*-, R 3 , X, Y and Z have the meanings given for formula I, preferably Z is NR 5 and R 5 is benzyl, with a compound of the formula XVI
  • R 4 and R 2 have the meanings given for formula I except for hydrogen, preferably R 4 and R 22 are i-propyl, in an inert solvent, preferably dichloromethane, in the presence of a base and of a silylating agent, preferably trimethylsilyl trifluoromethanesulfonate or tert.-butyldimethylsilyltrifluoromethanesulfonate at temperatures of from -78°C to 40°C and cleavage of the resulting silyl ether with a cleaving agent, preferably tetrabutylammoniumfluoride in an inert solvent, preferably tetrahydrofurane, in the presence of a base.
  • a silylating agent preferably trimethylsilyl trifluoromethanesulfonate or tert.-butyldimethylsilyltrifluoromethanesulfonate at temperatures of from -78°C to 40°C and
  • Process variants 1), 2) and 3) have been developed specifically for the preparation of the active ingredients of the formula I.
  • the present invention therefore likewise relates to them.
  • Compounds of the formula Vm are known and are described, for example, in Danishefsky, S.; Webb ⁇ , R.RJ. Org. Chem. 1984, 49, 1955, Gue ⁇ y, P.; Neier, R.; Synthesis, 1984, 485; Kozikowski, A.P.; Park, P.; J Org. Chem., 1990, 55, 4688; Ziegler, F.E.; Bennet, G.B.; J. Am. Chem.
  • the compounds of the formula I are employed in unaltered form, as obtainable by the synthesis, or preferably together with the auxiliaries conventionally used in formulation technology, and they are therefore processed in a known manner to give, for example, emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules, and also encapsulations, for example in polymeric substances.
  • the application methods such as spraying, atomising, dusting, scattering or pouring, as well as the type of compositions are selected to suit the intended aims and the prevailing circumstances.
  • compositions, preparations or combinations comprising the active substance of the formula I and, if desired, one or more solid or liquid additives, are prepared in a known manner, for example by intimately mixing and/or grinding the active substances with extenders, for example with solvents, solid carriers and, if desired, surface-active compounds (surfactants).
  • extenders for example with solvents, solid carriers and, if desired, surface-active compounds (surfactants).
  • aromatic hydrocarbons in particular the fractions C 8 to C 12 , such as mixtures of alkylbenzenes, for example xylene mixtures or alkylated naphthalenes; aliphatic and cycloaliphatic hydrocarbons such as paraffins, cyclohexane or tetrahydronaphthalene; alcohols, such as ethanol, propanol or butanol; glycols as well as their ethers and esters, such as propylene glycol or dipropylene glycol ether, ketones such as cyclohexanone, isophorone or diacetone alcohol, strongly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or water; vegetable oils as well as their esters, such as rapeseed oil, castor oil or soybean oil; and if appropriate also silicone oils.
  • aromatic hydrocarbons in particular the fractions C 8 to C 12 , such as mixtures of alkylbenzenes, for example
  • Suitable surface-active compounds are non-ionic, cationic and/or anionic surfactants having good emulsifying, dispersing and wetting properties, depending on the nature of the active substance of the formula I to be formulated.
  • Surfactants are also to be understood as meaning mixtures of surfactants.
  • Anionic surfactants which are suitable can be either so-called water-soluble soaps or water-soluble synthetic surface-active compounds.
  • Suitable soaps which may be mentioned are the alkali metal salts, alkaline earth metal salts or substituted or unsubstituted ammonium salts of higher fatty acids (C 10 -C 22 ), such as the Na salts or K salts of oleic or stearic acid, or of natural mixtures of fatty acids which can be obtained, for example, from coconut oil or tallow oil. Mention must also be made of the fatty acid methyltaurinates.
  • the fatty alcohol sulfonates or fatty alcohol sulfates are generally in the form of alkali metal salts, alkaline earth metal salts or substituted or unsubstituted ammonium salts, and have an alkyl radical having 8 to 22 C atoms, alkyl also including the alkyl moiety of acyl radicals, for example the Na or Ca salt of ligninsulfonic acid, of the dodecylsulfuric ester or of a fatty alcohol sulfate mixture prepared from natural fatty acids.
  • This group also includes the salts of the sulfuric esters and sulfonic acids of fatty alcohol/ethylene oxide adducts.
  • the sulfonated benzimidazole derivatives preferably contain 2 sulfonyl groups and one fatty acid radical having 8 to 22 C atoms.
  • alkylarylsulfonates are the Na, Ca or triethanolamine salts of dodecylbenzenesulfonic acid, of dibutylnaphthalenesulfonic acid or of a naphthalenesulfonic acid/formaldehyde condensation product.
  • Suitable compounds are the corresponding phosphates, such as the salts of the phosphoric ester of a p-nonylphenol/(4- 14) -ethylene oxide adduct, or phospholipids.
  • Suitable non-ionic surfactants are mainly polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, of saturated or unsaturated fatty acids and of alkylphenols, which can contain 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to 18 carbon atoms in the alkyl radical of the alkylphenols.
  • non-ionic surfactants which are suitable are the water-soluble polyethylene oxide adducts with polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol which have 1 to 10 carbon atoms in the alkyl chain and which contain 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups.
  • the abovementioned compounds customarily contain 1 to 5 ethylene glycol units per propylene glycol unit.
  • non-ionic surfactants examples include nonylphenolpolyethoxyethanols, castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol.
  • Suitable substances are fatty acid esters of polyoxyethylenesorbitan, such as polyoxyethylenesorbitan trioleate.
  • the cationic surfactants are mainly quaternary ammonium salts, which contain at least one alkyl radical having 8 to 22 C atoms as N-substituents and which have lower halogenated or free alkyl, benzyl or lower hydroxyalkyl radicals as further substituents.
  • the salts are preferably in the form of halides, methylsulfates or ethylsulfates, for example stearyltrimethylammonium chloride or benzyldi(2-chloroethyl)ethylammonium bromide.
  • the pesticidal preparations contain 0.1 to 99 %, in particular 0.1 to 95 %, of the active substance of the formula 1, 1 to 99 % of a solid or liquid additive and 0 to 25 %, in particular 0.1 to 25 %, of a surfactant.
  • compositions are more preferred as commercial goods, the user generally uses dilute compositions.
  • the compositions can also comprise further additives such as stabilisers, for example epoxidised or unepoxidised vegetable oils (epoxidised coconut oil, rapeseed oil or soybean oil), defoamers, for example silicone oil, preservatives, viscosity regulators, binders, tackifiers, as well as fertilisers or other active substances for achieving specific effects.
  • stabilisers for example epoxidised or unepoxidised vegetable oils (epoxidised coconut oil, rapeseed oil or soybean oil), defoamers, for example silicone oil, preservatives, viscosity regulators, binders, tackifiers, as well as fertilisers or other active substances for achieving specific effects.
  • Emulsifiable concentrates Active ingredient: 1 to 20 , preferably 5 to 10 %
  • Surface-active agent 5 to 30 %
  • Liquid carrier 15 to 94 , preferably 70 to 85 %
  • Active ingredient 0.1 to 10 %, preferably 0J to 1 %
  • Solid carrier 99.9 to 90 %, preferably 99.9 to 99 %
  • Suspension concentrates Active ingredient: 5 to 75 %, preferably 10 to 50 % Water: 94 to 24 %, preferably 88 to 30 % Surface-active agent: 1 to 40 %, preferably 2 to 30 %
  • Wettable powders Active ingredient: 0.5 to 90 %, preferably 1 to 80 %
  • Surface-active agent 0.5 to 20 %, preferably 1 to 15 %
  • Solid carrier 5 to 95 %, preferably 15 to 90 %
  • Granules Active ingredient: 0.5 to 30 %, preferably 3 to 15 %
  • Solid carrier 99.5 to 70 %, preferably 97 to 85 %
  • the active substances of the formula I are sucessfully employed at application rates from 0.001 to 10 kg/ha, in particular 0.005 to 2 kg/ha.
  • the dosage rate which is required for the desired action can be determined by tests. It depends on the nature of the action, the development stage of the crop plant and the weed, as well as on the application (location, time, method) and, due to these parameters, can vary within wide limits. Controlled release of active substance
  • the dissolved active substance is applied to mineral granule carriers or polymerised granules (urea/formaldehyde) and allowed to dry. If desired, a coating can be applied (coated granules), which permits slow release of the active substance over a certain period.
  • Wettable powder a) b) c) Active ingredient according to
  • the active ingredient is mixed thoroughly with the additives and the mixture is ground thoroughly in a suitable mill. Wettable powders which can be diluted with water to give suspensions of any desired concentration are obtained.
  • Emulsion concentrates a) b) active ingredient according to
  • Emulsions of any desired concentation can be prepared from such concentrates by dilution with water.
  • Dusts a) b) Active ingredient according to
  • Ready-to-use dusts are obtained by intimate mixing of the carriers with the active ingredient.
  • the active ingredient is mixed with the additives and the mixture is ground and moistened with water. This mixture is extruded and the extrudate is then dried in a stream of air.
  • the finely ground active ingredient is applied uniformly to the kaolin, which has been moistene with polyethylene glycol, in a mixer. Dust-free coated granules are obtained in this manner.
  • a suspension concentrate is thus obtained, from which suspensions of any desired concentration can be prepared by dilution with water.
  • the compounds of the formula I are employed in unchanged form or, preferably, as compositions together with the auxiliaries customary in formulation technology, and are therefore processed in a known manner for example to emulsion concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules and also capsules in, for example, polymeric substances.
  • the methods of use such as spraying, misting, dusting, scattering or pouring, like the nature of the compositions, are chosen according to the desired effets and the given circumstances.

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

Abstract

Un triazole de la formule (I) dans laquelle les notations des radicaux sont décrites dans la revendication 1, présente de bonnes propriétés herbicides sélectives avant et après l'émergence végétale, et de régulation de la croissance végétale. Ces dérivés sont appropriés en tant que substances actives pour désherbants et pour des compositions destinées à inhiber la croissance végétale.
EP95903443A 1994-01-06 1995-01-03 Derives de l'acide phosphonique contenant un cycle triazole, utilises en tant qu'herbicides Withdrawn EP0738271A1 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
GB9400178 1994-01-06
GB9400178A GB9400178D0 (en) 1994-01-06 1994-01-06 Novel triazoles
GB9407233A GB9407233D0 (en) 1994-04-12 1994-04-12 Novel triazoles
GB9407233 1994-04-12
PCT/IB1995/000004 WO1995018811A1 (fr) 1994-01-06 1995-01-03 Derives de l'acide phosphonique contenant un cycle triazole, utilises en tant qu'herbicides

Publications (1)

Publication Number Publication Date
EP0738271A1 true EP0738271A1 (fr) 1996-10-23

Family

ID=26304129

Family Applications (1)

Application Number Title Priority Date Filing Date
EP95903443A Withdrawn EP0738271A1 (fr) 1994-01-06 1995-01-03 Derives de l'acide phosphonique contenant un cycle triazole, utilises en tant qu'herbicides

Country Status (8)

Country Link
EP (1) EP0738271A1 (fr)
JP (1) JPH09507243A (fr)
AU (1) AU1249495A (fr)
BR (1) BR9506458A (fr)
CA (1) CA2179822A1 (fr)
IL (1) IL112247A0 (fr)
MD (1) MD960284A (fr)
WO (1) WO1995018811A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113968883A (zh) * 2020-07-23 2022-01-25 南京工业大学 光学色酮衍生物及其制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0528760A1 (fr) * 1991-08-09 1993-02-24 Japat Ltd Nouveaux triazoles
GB9202779D0 (en) * 1992-02-10 1992-03-25 Ici Plc Novel compounds

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9518811A1 *

Also Published As

Publication number Publication date
AU1249495A (en) 1995-08-01
MD960284A (ro) 1998-07-31
WO1995018811A1 (fr) 1995-07-13
IL112247A0 (en) 1995-03-30
JPH09507243A (ja) 1997-07-22
CA2179822A1 (fr) 1995-07-13
BR9506458A (pt) 1997-10-28
MX9602657A (es) 1998-06-28

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