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WO1992019629A1 - Nouveaux composes de triazole - Google Patents

Nouveaux composes de triazole Download PDF

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Publication number
WO1992019629A1
WO1992019629A1 PCT/JP1992/000485 JP9200485W WO9219629A1 WO 1992019629 A1 WO1992019629 A1 WO 1992019629A1 JP 9200485 W JP9200485 W JP 9200485W WO 9219629 A1 WO9219629 A1 WO 9219629A1
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WO
WIPO (PCT)
Prior art keywords
group
formula
triazol
represented
compound
Prior art date
Application number
PCT/JP1992/000485
Other languages
English (en)
Inventor
Ichiro Mori
Genji Iwasaki
Alfred Scheidegger
Shinichi Koizumi
Kenji Hayakawa
Junichi Mano
Original Assignee
Japat Ltd.
Ciba-Geigy (Japan) Limited
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 Japat Ltd., Ciba-Geigy (Japan) Limited filed Critical Japat Ltd.
Priority to EP92908257A priority Critical patent/EP0636135A1/fr
Priority to JP4507777A priority patent/JPH06507156A/ja
Priority to CA002107082A priority patent/CA2107082A1/fr
Publication of WO1992019629A1 publication Critical patent/WO1992019629A1/fr

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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
    • 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
    • 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
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Definitions

  • This invention relates to novel triazole compounds, processes for preparing the same, compositions containing the same, as well as, applications of the compounds in the technical fields of herbicides and microbicides.
  • Triazole compounds which have a herbicidal action are generally known.
  • European Patent Application No. 0078 613 describes herbicidally active triazole compounds.
  • this invention relates to novel compounds represented by formula (1):
  • R 1 represents a hydrogen atom or a group A which is a protective group or is C 1 -C 4 -alkyl
  • X and Y jointly represent a carbonyl group together with the carbon atom to which they are bonded, or X and Y each independently represent a hydrogen atom or a -OR 2 group, wherein R 2 represents a hydrogen atom, a lower alkyl group, an acetyl group, a benzyl group or a silyl group represented by -SiR' 3 (wherein R' represents an alkyl group); and Z represents a -CH 2 PO(OR 3 ) 2 or -CH 2 OPO(OR 3 ) 2 group (wherein R 3 represents a hydrogen atom, a lower alkyl group, a benzyl group, a phenyl group, a cyanoethyl group, an allyl group, a CH 2 OH group, a COOR 5 group, or an alkali metal, alkaline earth
  • n 0 or 1
  • R 5 is a C 1 -C 6 -alkyl group.
  • This invention includes all of the isomers represented by the following formula of resonance structure:
  • R 1 , n, X, Y and Z have the meanings as definded in formula (1).
  • the present compound includes two kinds of compounds; one is phosphate compounds and the other phosphonate compounds.
  • Alkyl is, for example, methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, sec-butyl, tert-butyl and the various isomeric pentyl or hexyl radicals.
  • the term "lower alkyl group' is preferably methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, sec-butyl or tert-butyl.
  • the meaning -SiR 3 also includes, for example, -Si(CH 3 ) 3 , Si(C 2 H 5 ) 2 CH 3 or Si(CH 3 ) 2 -CH(CH 3 ) 3 .
  • -CH 2 OPO(OR 3 ) 2 can be prepared by: forming a ((1,2,4)-triazol-5-yI)propionic acid ester represented by formula (7):
  • R 4 represents an alkyl group
  • A has the same meaning as defined below, from a ((1,2,4)-triazol-5-yl)aldehyde represented by formula (6):
  • A represents a protective group
  • R' represents an alkyl group
  • a and R 4 have the same meanings as defined above, reducing the 3-alkylsilyloxy-3-((1,2,4)-triazol-5-yl)-propionic acid ester to form a 3-alkylsilyloxy-3-((1,2,4)-triazol-5-yl)-1-propanol represented by the formula (9):
  • R' and A have the same meanings as defined above; reacting the 3-alkylsilyloxy-3-((1,2,4)-triazol-5-yl)-1-propanol with a suitable phosphine compound followed by desilylation to form a
  • R 3 and A have the same meaning as defined above; and convening, as necessary, the 3-hydroxy-3-((1,2,4)-triazol-5-yl)propyl-phosphate to
  • the compounds of the formula (1), wherein n is 0 and Z represents -CH 2 OPO(OR 3 ) 2 can be prepared by: forming a 2-((1,2,4)-triazol-5-yl)-2-oxoacetic acid ester represented by formula (11):
  • R 4 represents an alkyl group
  • A has the same meaning as defined below, from a (1,2,4)-triazole represented by formula (12):
  • A represents a group which is a protective group or is C 1 -C 4 -alkyl; isomerizing the 2-((1,2,4)-triazol-5-yl)-2-oxoacetic acid ester thus formed to form 2-((1,2,4)-triazol-3- yl)-2-oxoacetic acid ester represented by formula (13):
  • a and R 4 have the same meanings as defined above; reducing the 2-((1,2,4)-triazol-3-yl)-2-oxoacetic acid ester followed by silylation to form 2-((1,2,4)-triazol-3-yl)-2-alkylsilyloxy-acetic acid ester represented by formula (14): wherein R' represents an alkyl group; and A and R 4 have the same meanings as defined above, reducing the 2-alkylsilyloxy-2-((1,2,4)-triazol-3-yl)acetic acid ester to form a 2-alkylsilyloxy-2-((1,2,4)-triazol-3-yl)-1-ethanol represented by formula (15):
  • a and R 3 have the same meaning as defined above; and converting, as necessary, the 2-hydroxy-2-((1,2,4)-triazol-3-yl)ethyl-phosphate to 2-hydroxy-2-((1,2,4)-triazol-3-yl)-ethyl-phosphate (mono or triester form); whereas the compounds of formula (1), wherein n is 1 and Z represents -CH 2 PO(OR 3 ) 2 can be prepared by reacting a (1,2,4)-triazole represented by formula (12):
  • A represents a group which is a protective group or is C 1 -C 4 -alkyl; with an aldehyde compound represented by the formula (23): wherein R 3 has the same meaning as defined above, to form a
  • R 3 and A have the same meanings as defined above; converting the 3-((1,2,4)- triazol-5-yl)-3-hydroxypropyl-phosphonate to 3-(1H-1,2,4-triazol-5-yl)-3-hydroxypropyl-phosphonic acid or phosphonate or oxidizing said 3-((1,2,4)triazol-5-yl)-3- hydroxypropyl-phosphonate to form a 3-((1,2,4)-triazol-5-yl)-3-oxopropyl-phosphonate represented by formula (25)
  • R 3 and A have the same meanings as defined above, followed by conversion into 3-(1H-1,2,4-triazol-5-yl)-3-oxopropyl-phosphonic acid or phosphonate.
  • a as a protective group may not be limited so long as it is conventionally used for inhibiting the reaction of triazole ring in synthetic organic chemistry and includes, for example, triphenylmethyl group, benzyl group, tert-butoxycarbonyl group, allyl group and sulfonyl group.
  • R 1 ' represents a hydrogen atom or C 1 -C 4 -alkyl
  • X and Y jointly represent a carbonyl group together with the carbon atom to which they are bonded, or X and Y each independently represent a hydrogen atom or a -OR 2 group, wherein R 2 represents a hydrogen atom, a lower alkyl group, an acetyl group, a benzyl group or a silyl group represented by -SiR' 3 (wherein R' represents an alkyl group); and Z' represents a
  • R 3 represents a hydrogen atom, a lower alkyl group, a benzyl group, a phenyl group, a cyanoethyl group, an allyl group, or an alkali metal, alkaline earth metal, ammonium, organic ammonium, trialkylsulphonium, trialkylsulfoxonium, phosphonium or amidinium cation; and
  • n 0 or 1; and the above intermediate compounds, and therefore constitute the gist of this invention.
  • Preferred compounds of the formula (1) are those, in which
  • R 1 represents a hydrogen atom or a group A which is a protective group
  • X and Y jointly represent a carbonyl group together with the carbon atom to which they are bonded, or X and Y each independently represent a hydrogen atom or a -OR 2 group, wherein R 2 represents a hydrogen atom, a lower alkyl group, an acetyl group, a benzyl group or a silyl group represented by -SiR' 3 (wherein R' represents an alkyl group); and Z represents a
  • R 3 represents a hydrogen atom, a lower alkyl group, a benzyl group, a phenyl group, a cyanoethyl group or an allyl group or a CH 2 OH group or a COOR 5 group,
  • n 1;
  • R 5 is an alkyl group, preferably a C 1 -C 4 -aIkyl group.
  • Preferred compounds of the formula (2) are those, in which R 1 ' represents a hydrogen atom ; X and Y jointly represent a carbonyl group together with the carbon atom to which they are bonded, or X and Y each independently represent a hydrogen atom or a -OR 2 group, wherein R 2 represents a hydrogen atom, a lower alkyl group, an acetyl group, a benzyl group or a silyl group represented by -SiR' 3 (wherein R' represents an alkyl group); and Z' represents a -CH 2 PO(OR 3 ) 2 or -CH 2 OPO(OR 3 ) 2 group (wherein R 3 represents a hydrogen atom, a lower alkyl group, a benzyl group, a phenyl group, a cyanoethyl group, an allyl group, or an alkali metal, alkaline earth metal, ammonium, organic ammonium, trialkylsulphonium, trialkylsul
  • n is 0 or 1, preferably 1.
  • the compounds of formula (I), in particular represented by formula (2), are distinguished by microbicidal and herbicidal properties which render them excellent for use in crops of useful plants, in particular in cereals, cotton, soya, rape, maize and rice.
  • the invention also relates to herbicidal and microbicidal compositions which comprise a novel active ingredient of formula (2), and methods for inhibition of plant growth.
  • the active ingredients of formula (2) are as a rule employed successfully at rates of application of 0.001 to 4 kg/ha, in particular 0.005 to 2 kg/ha.
  • the doses required for the desired action can be determined by experiments. It depends on the nature of the action, the development stage of the crop plant and of the weed and on the application conditions (location, time, method) and can, as a result of these parameters, be varied within wide ranges.
  • the compounds of formula (2) 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 formula (2) 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).
  • 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 sulf oxide 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 formula (2) 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
  • 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 butyl-ionic surfactants
  • nonylphenolpolyethoxyethanols castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and
  • 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
  • the pesticidal preparations contain 0.1 to 99 %, in particular 0.1 to 95 %, of the active substance of formula (2), 1 to 99 % of a solid or liquid additive and 0 to 25 %, in particular 0.1 to 25 %, of a surfactant.
  • 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 are:
  • Active ingredient 1 to 90 %, preferably 5 to 20 %
  • Liquid carrier 50 to 94 %, preferably 70 to 85 %
  • Active ingredient 5 to 75 %, preferably 10 to 50 %
  • the active substances of formula (2) 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.
  • 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.
  • This invention further relates to the use of at least one of the compounds represented by formula (2) as the active ingredient for inhibiting enzymes which participate in the biosynthesis of histidine.
  • a phosphate compound of this invention was prepared according to the flow charts shown below:
  • IR (neat, cm -1 ): 3430, 3150, 3070, 3000, 1730, 1600, 1530, 1490, 1470, 1450, 1400, 1375,
  • IR (neat, cm -1 ): 2950, 2930, 2855, 1735, 1595, 1490, 1470, 1445, 1370, 1250, 1170, 1103, 1030, 1000, 955, 880, 840, 780, 760, 700
  • IR (neat, cm -1 ): 3375, 3060, 3030, 2950, 2850, 2880, 1600, 1510, 1490, 1450, 1390, 1360, 1325, 1250, 1190, 1170, 1000, 1030, 985, 940, 905, 880, 840, 770, 700, 670, 640
  • IR (neat, cm -1 ): 3350, 3070, 3025, 2975, 2940,2910, 2875, 1720, 1670, 1600, 1510, 1495, 1478, 1450, 1395, 1370, 1345, 1330, 1250, 1170, 1100, 1020, 920, 880, 830, 800, 750, 705, 670, 640
  • a phosphate compound of this invention was prepared according to the flow charts shown below:
  • IR (neat, cm -1 ): 3060, 2955, 2925, 2900, 2860, 1760, 1738, 1595, 1490, 1470, 1460, 1445, 1370, 1360, 1340, 1330, 1250, 1130, 1030, 1000, 940, 880, 840, 780, 750, 700
  • IR NaCl, cm -1 : 3350, 2925, 2850, 1600, 1505, 1490, 1470, 1460, 1445, 1355, 1250, 1170, 1100, 1060, 1040, 955, 870, 840, 780, 750, 700
  • IR (neat, cm -1 ): 3060, 3040, 2950, 2925, 2880, 2855, 1517, 1492, 1475, 1380, 1350, 1310, 1285, 1215, 1070, 1060, 1130, 1085, 1010, 910, 878, 840, 780, 750, 700
  • a phosphonate compound of this invention was prepared according to the flow charts shown below:
  • the mixture was quenched to -78°C, and 5 ml of an aqueous NH 4 Cl was added thereto.
  • IR (NaCl) cm -1 3340, 1595, 1490, 1445, 1240, 1200, 1060, 1030, 960, 755, 700
  • the thus obtained compound corresponds to the substance of the Compound No. 1 in Table 1.
  • IR (NaCl) cm -1 2680, 1720, 1485, 1450, 1260, 1060, 1030, 960, 860, 801, 750, 700
  • Emulsions of any desired concentration can be prepared from such concentrates by diluting them with water.
  • glycol ether (15 mol of EO) 1 % 6 %
  • the finely-ground active substance is mixed intimately with the additives. This gives a suspension concentrate, from which suspensions of any desired concentration can be prepared by diluting it with water.
  • the compounds of the formula (2) are employed as such or preferably as compositions together with the auxiliaries customary in formulation technology, and they are therefore processed in a known manner to give, for example, emulsion concentrates, directly sprayable or dilutable solutions, dilute emulsions, sprayable 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.
  • Example B1 Herbicidal action before emergence of the plants
  • test plants are seeded out in plastic pots containing standard soil. Immediately after seeding, the pots are being sprayed with an aqueous suspension of the compound No. 102. The rate corresponds to 4000g a.i./ha.
  • the treated pots are then placed in the greenhouse at temperatures of 18°C (night) and 24°C (day). Appr. 3 weeks after treatment, the emerged plants are evaluated in terms of herbicidal symtoms:
  • test plants are seeded out in plastic pots containing standard soil and raised in the greenhouse at 18°C (night) and 24°C (day). Appr. 10 to 20 days after seeding (depending of individual growth-rate), foliar treatment takes place with an aqueous suspension of the compound No. 102. The rate corresponds to 2000g a.i./ha. Appr. 2 weeks after treatment, the emerged plants are evaluated in terms of herbicidal symtoms:

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  • Life Sciences & Earth Sciences (AREA)
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  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
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Abstract

Nouveau composé de triazole répondant à la formule (1) dans laquelle R1 représente un atome d'hydrogène ou un groupe A qui est un groupe protecteur ou un groupe alkyle C1-C4; X et Y représentent ensemble un groupe carbonyle avec l'atome de carbone auquel ils sont liés, ou bien X et Y représentent indépendamment l'un de l'autre un atome d'hydrogène ou un groupe -OR2 où R2 représente un atome d'hydrogène, un groupe alkyle inférieur, un groupe acétyle, un groupe benzyle ou un groupe silyle représenté par -SiR'3 (où R' représente un groupe alkyle); et Z représente un groupe -CH2PO(OR3)2 ou -CH2OPO(OR3)2 où R3 représente un atome d'hydrogène, un groupe alkyle inférieur, un groupe benzyle, un groupe phényle, un groupe cyanoéthyle, un groupe allyle, un groupe CH2OH, un groupe COOR5, ou bien un cation métal alcalin, un cation métal alcalino-terreux, un cation ammonium, un cation ammonium organique, un cation trialkylsulfonium, un cation trialkylsulfoxonium, un cation phosphorium ou d'amidinium; n vaut 0 ou 1; et R5 représente un groupe alkyle C1-C6. L'invention concerne également un procédé de préparation de ce nouveau composé, une composition contenant ledit composé, ainsi que l'utilisation de celui-ci dans le domaine des herbicides et des microbicides.
PCT/JP1992/000485 1991-04-27 1992-04-17 Nouveaux composes de triazole WO1992019629A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP92908257A EP0636135A1 (fr) 1991-04-27 1992-04-17 Nouveaux composes de triazole
JP4507777A JPH06507156A (ja) 1991-04-27 1992-04-17 トリアゾール化合物
CA002107082A CA2107082A1 (fr) 1991-04-27 1992-04-17 Composes triazole

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JP12551091 1991-04-27
JP3/125510 1991-04-27

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AU (1) AU1554492A (fr)
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993015610A1 (fr) * 1992-02-10 1993-08-19 Zeneca Limited Derives d'acide phosphonique renfermant un noyau triazole, et utilisation comme herbicides
WO1995014385A1 (fr) * 1993-11-24 1995-06-01 Agrevo Uk Limited Pesticides a base de phosphonate de triazole
WO2000024867A3 (fr) * 1998-10-23 2001-09-20 Du Pont Enzymes de biosynthese de l'histidine vegetale
US6489476B1 (en) 1998-09-09 2002-12-03 Metabasis Therapeutics, Inc. Heteroaromatic compounds containing a phosphonate group that are inhibitors of fructose-1,6-bisphosphatase
US7563774B2 (en) 2000-06-29 2009-07-21 Metabasis Therapeutics, Inc. Combination of FBPase inhibitors and antidiabetic agents useful for the treatment of diabetes
CN113683574A (zh) * 2021-09-06 2021-11-23 上海晋鲁医药科技有限公司 一种合成1-甲基-1h-1,2,4-三唑-3-甲酸甲酯的方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0065216A1 (fr) * 1981-05-08 1982-11-24 Hoechst Aktiengesellschaft S-(triazol-1.2.4-yl-5-méthyl-) (di)-thiophosph(on)ates et procédé pour les préparer
EP0078613A1 (fr) * 1981-11-02 1983-05-11 Imperial Chemical Industries Plc Dérivés d'acide propylphosphonique substitué, leur utilisation comme herbicides, compositions herbicides les contenant et procédé pour les préparer
EP0275821A1 (fr) * 1986-11-21 1988-07-27 Ciba-Geigy Ag Acides alcanediphosphoniques substitués

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EP0065216A1 (fr) * 1981-05-08 1982-11-24 Hoechst Aktiengesellschaft S-(triazol-1.2.4-yl-5-méthyl-) (di)-thiophosph(on)ates et procédé pour les préparer
EP0078613A1 (fr) * 1981-11-02 1983-05-11 Imperial Chemical Industries Plc Dérivés d'acide propylphosphonique substitué, leur utilisation comme herbicides, compositions herbicides les contenant et procédé pour les préparer
EP0275821A1 (fr) * 1986-11-21 1988-07-27 Ciba-Geigy Ag Acides alcanediphosphoniques substitués

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993015610A1 (fr) * 1992-02-10 1993-08-19 Zeneca Limited Derives d'acide phosphonique renfermant un noyau triazole, et utilisation comme herbicides
US5393732A (en) * 1992-02-10 1995-02-28 Zeneca Limited Triazole phosphoric acid derivatives and their use as herbicides
WO1995014385A1 (fr) * 1993-11-24 1995-06-01 Agrevo Uk Limited Pesticides a base de phosphonate de triazole
US6489476B1 (en) 1998-09-09 2002-12-03 Metabasis Therapeutics, Inc. Heteroaromatic compounds containing a phosphonate group that are inhibitors of fructose-1,6-bisphosphatase
US7312219B2 (en) 1998-09-09 2007-12-25 Metabasis Therapeutics, Inc. Heteroaromatic inhibitors of fructose 1,6-bisphosphatase
WO2000024867A3 (fr) * 1998-10-23 2001-09-20 Du Pont Enzymes de biosynthese de l'histidine vegetale
US6441271B1 (en) 1998-10-23 2002-08-27 E. I. Du Pont De Nemours And Company Plant histidine biosynthetic enzymes
US7563774B2 (en) 2000-06-29 2009-07-21 Metabasis Therapeutics, Inc. Combination of FBPase inhibitors and antidiabetic agents useful for the treatment of diabetes
CN113683574A (zh) * 2021-09-06 2021-11-23 上海晋鲁医药科技有限公司 一种合成1-甲基-1h-1,2,4-三唑-3-甲酸甲酯的方法
CN113683574B (zh) * 2021-09-06 2023-11-17 上海晋鲁医药科技有限公司 一种合成1-甲基-1h-1,2,4-三唑-3-甲酸甲酯的方法

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AU1554492A (en) 1992-12-21
JPH06507156A (ja) 1994-08-11
EP0636135A1 (fr) 1995-02-01
CA2107082A1 (fr) 1992-10-28

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