EP0440659A1 - Herbicides a base de phenyltriazolopyrimidine a substitution - Google Patents

Herbicides a base de phenyltriazolopyrimidine a substitution

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Publication number
EP0440659A1
EP0440659A1 EP89908575A EP89908575A EP0440659A1 EP 0440659 A1 EP0440659 A1 EP 0440659A1 EP 89908575 A EP89908575 A EP 89908575A EP 89908575 A EP89908575 A EP 89908575A EP 0440659 A1 EP0440659 A1 EP 0440659A1
Authority
EP
European Patent Office
Prior art keywords
och
chf
formula
compound
methyl
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.)
Pending
Application number
EP89908575A
Other languages
German (de)
English (en)
Inventor
Thomas Paul Selby
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of EP0440659A1 publication Critical patent/EP0440659A1/fr
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Definitions

  • R 1 is H or alkyl
  • EP-A-220,458 published May 6, 1987 (German priority September 28, 1985) and EP-A-217, 218, published April 8, 1987 (German priority
  • A is N, CH, C(alkyl) CBr or CCl.
  • R 1 includes phenyl and substituted phenyl.
  • R 1 is H, SCN, SCH 3 , Ph or CH 3 ;
  • R 2 is H or CH 3 and
  • R 3 is SH, SCH 2 Ph or SCH 2 CO 2 H.
  • This invention comprises compounds of Formula I, agriculturally suitable compositions containing them, and their method-of-use as preemergence and/or postemergence herbicides
  • G and G 1 are N or C
  • R 1 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl,
  • R 2 is halogen, NO 2 , OR 3 , S(O) n R 3 , OSO 2 R 3 , C 1 -C 4 haloalkyl, C 3 -C 4 halocycloalkyl, C 3 -C 4 haloalkynyl or C 2 -C 4 haloalkenyl;
  • R 3 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 3 -C 4 alkynyl, C 3 -C 4 haloalkynyl, or C 3 -C 4 halocycloalkyl;
  • R 4 is H, halogen, C 1 -C 3 alkoxy, C 1 -C 3 alkyl or CF 3 ;
  • R 5 is H, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, NO 2 , OR 3 , S(O) n R 3 , OSO 2 R 3 , phenyl, phenoxy, C 2 -C 4 alkoxycarbonyl, C 2 -C 4 al
  • n O, 1 or 2;
  • R 6 is H or F
  • X, Y and Z are independently CR 7 or N;
  • R 7 is H, CN, halogen, NO 2 , CO 2 R 3 , C 1 -C 3 alkyl, C 1 -C 3 haloalkyl or CONH 2 ;
  • Z can be CR 7 .
  • alkyl used either alone or in compound words such as
  • alkylthio denotes straight chain or branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl or the different butyl isomers.
  • Alkoxy denotes methoxy, ethoxy, n-propoxy, isopropoxy and the different butoxy isomers.
  • Alkenyl denotes straight chain or branched alkenes, e.g., vinyl, 1-propenyl, 2-propenyl,
  • Alkynyl denotes straight chain or branched alkynes, e.g., ethynyl, 1-propynyl, 2-propynyl and the different butynyl isomers.
  • halogen denotes fluorine, chlorine, bromine or iodine.
  • haloalkyl or halocycloalkyl denotes mono to per-halogentaed alkyl isomers e.g.
  • substitutent group is indicated by the C i -C j prefix where i and j are numbers from 1 to 4.
  • C 3 -C 4 alkenyl would designate propenyl through butenyl.
  • G is CH and G 1 is N (Formula la); or
  • G is N and G 1 is CH (Formula lb).
  • X is CR 7 ;
  • Y is N
  • X is CR 7 ;
  • Y is N
  • X is N
  • Y is CR 7 ;
  • Formula I is lb ;
  • X is N
  • Y is N
  • Z is CR 7 .
  • X is N
  • Y is N
  • Z is CR 7 .
  • X is N
  • Y is N
  • Formula I is lb
  • X is N
  • Y is N
  • R 6 is H
  • R 1 is C 1 -C 3 alkyl, SCH 3 , NHCH 3 , CH 2 OCH 3 or CH 2 SCH 3 . 11.
  • R 3 is CH 2 CH 2 F, CH 2 CF 3 , CH(CH 3 )CF 3 ,
  • R 5 is H, halogen, OCH 3 , OCF 2 H, OCH 2 CF 3 , SCF 3 , C 1 -C 3 alkyl, OCF 3 , OCH 2 CHF 2 , OCH 2 CF 3 , OCH 2 CH 2 F, SCHF 2 , CF 3 , CHF 2 , CF 2 Cl, CH 2 CF 3, CH 2 F, CCI 3 , CH 2 Cl or CN and R 5 is in the meta position.
  • R 1 is C 1 -C 3 alkyl. 15.
  • R 1 is C 1 -C 3 alkyl
  • R 3 is CH 2 CH 2 F, CH 2 CF 3 , CH(CH 3 )CF 3 ,
  • R 4 is H
  • R 5 is H, halogen, OCH 3 , OCF 2 H, OCH 2 CF 3 , SCF 3 , C 2 -C 3 alkyl, OCF 3 , OCH 2 CHF 2 , OCH 2 CH 2 F, SCHF 2 , CF 3 , CHF 2 , CF 2 Cl, CH 2 CF 3 , CH 2 F, CCl 3 , CH 2 Cl or CN and R 5 is in the meta position; and
  • R 6 is H.
  • R 1 is C 1 -C 3 alkyl
  • R 3 is CH 2 CH 2 F, CH 2 CF 3 , CH(CH 3 )CF 3 ,
  • R 4 is H
  • R 5 is H, halogen, OCH 3 , OCF 2 H, OCH 2 CF 3 , SCF 3 , C 2 -C 3 alkyl, OCF 3 , OCH 2 CHF 2 , OCH 2 CH 2 F, SCHF 2 , CF 3 , CHF 2 , CF 2 Cl, CH 2 CF 3 , CH 2 F, CCl 3 , CH 2 Cl or CN and R 5 is in the meta position;
  • R 6 is H
  • R 7 is CN. 17.
  • R 1 is C 1 -C 3 alkyl
  • R 2 is CF 3 , SCF 3 , SCF 2 H, OCF 3 , OCH 2 CHF 2 ,
  • CH CF 2 or 2, 2-diflurocyclopropane
  • R 3 is CH 2 CH 2 F, CH 2 CF 3 , CH(CH 3 )CF 3 ,
  • R 4 is H
  • R 5 is H, halogen, OCH 3 , OCF 2 H, OCH 2 CF 3 ,
  • R 6 is H
  • R 7 is CN.
  • R 1 is alkyl, alkenyl, alkoxyalkyl, alkyl substituted by halogen and R 2 , R 4 , R 5 and R 6 are defined as above.
  • This reaction is carried out by heating the reactants neat or in an inert polar protic or aprotic solvent at temperatures between 50° and 130°C. Suitable solvents are glacial acetic acid, ethanol, methanol, dimethylformamide, and dimethylsulfoxide.
  • Aminoheterocycles of Formula II can be prepared by synthetic methods reviewed in "The Chemistry of Heterocyclic Compounds” Volumes 6 (1953), 22 (1967), and 37 (1981), John Wiley & Sons.
  • Beta-diketones of Formula III can be synthesized by standard Claisen acylation procedures such as those taught by C. R. Hauser et. al. in Journal of American Chemical Society 67, pg. 284 (1945), 68, pg. 2742 (1946), 69 pg. 2649 (1947) and 70 pg . 4023 (1948).
  • a minor regio isomer la' can also be formed in the reaction shown in Scheme-1.
  • Compounds of Formula la are isolated pure, however, after aqueous workup, trituration, and subsequent purification by recrystallization or silica gel column chromatography. Silica gel column chromatography can also be used to isolate products of Formula la directly from the crude reaction residue obtained after reaction work up.
  • Scheme-2 illustrates the preparation of compounds of Formula la (where R 1 is hydrogen, alkylthio, or alkoxy and R 2 , R 4 , R 5 and R 6 are defined as above) by reaction of aminoheterocycles of Formula II with compounds of Formula IV where Q is a suitable leaving group such as dimethylamino, methylthio or methoxy.
  • Q is a suitable leaving group such as dimethylamino, methylthio or methoxy.
  • This reaction is carried out by heating reactants II and IV neat or in an inert polar protic or aprotic solvent such as glacial acetic acid, ethanol, methanol, dimethylformamide, or dimethylsufoxide at temperatures between 50° and 130°C.
  • Compounds of Formula IV can readily be prepared by one skilled in the art by known methods.
  • Scheme-4 illustrates the reaction of compounds of Formula VI (where K is O or S, G', X, Y, w, Z, R 1 , R 4 , R 5 and R 6 are defined as above) with an
  • alkylating agent of formula R 3 -Q' (where Q' is a suitable leaving group such as halogen and R 3 is defined as above) in a polar protic or aprotic solvent such as aqueous dioxane or dimethylformamide in the presence of a base such as a metal carbonate, metal hydroxide or metal alkoxide (where the metal is sodium or potassium) at temperatures between 0° and 70°C to give compounds of Formula Id.
  • Compounds of Formula VI can be prepared by the method shown in Scheme-1 where R 2 equals mercapto or hydroxyl.
  • Compounds of Formula IX can be prepared from compounds of Formula VII by reagents such as hydroxylamine-o-sulfonic acid, o-mesitylenesulfonyl hydroxylamine or o-diphenylphosphinylhydroxylamine as taught by K. T. Potts et al., J. Org, Chem.. 31, 260 (1961) and Y. Tamura et al., Tet. Lett.. 4133 (1972) and W. Klotzer et al., Synthesis. 592 (1982).
  • reagents such as hydroxylamine-o-sulfonic acid, o-mesitylenesulfonyl hydroxylamine or o-diphenylphosphinylhydroxylamine as taught by K. T. Potts et al., J. Org, Chem.. 31, 260 (1961) and Y. Tamura et al., Tet. Lett.. 4133 (1972) and W. Klo
  • Scheme-8 illustrates the preparation of compounds of Formula Ii from compounds of Formula X. The chemistry is analogous to that of Scheme-7.
  • Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable
  • Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation.
  • the formulations broadly, contain about 0.1% to 99% by weight of active ingredient (s) and at least one of
  • Wettable Powders 20-90 0-74 1-10 Oil Suspensions, 3-50 40-95 0-15
  • High Strength 90-99 0-10 0-2 Compositions Active ingredient plus at least one of a Surfactant or a Diluent equals 100 weight percent.
  • Emulsifiers Annual MC Publishing Corp., Ridgewood, New Jersey, as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.
  • compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Patent
  • Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering.
  • Example B The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged.
  • Example B The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged.
  • the ingredients are blended, coarsely hammer- milled and then air-milled to produce particles essentially all below 10 microns in diameter.
  • the product is reblended before packaging.
  • Example D A slurry of wettable powder containing 25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.
  • Example D A slurry of wettable powder containing 25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.
  • the ingredients are blended, hammer-milled and then moistened with about 12% water.
  • the mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings).
  • the granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.
  • the active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.
  • the ingredients are blended and milled to pass through a 100 mesh screen.
  • This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material.
  • the fluidization and spraying are continued until granules of the desired size range are made.
  • the spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1%.
  • the material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and
  • the ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns.
  • the material is sifted through a U.S.S. No. 50 screen and then packaged.
  • the ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size.
  • the material is reblended and then packaged.
  • the ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns.
  • the product can be used directly, extended with oils, or emulsified in water.
  • the active ingredient is blended with attapulgite and then passed through a hammer-mill to produce particles substantially all below 200 microns.
  • the ground concentrate is then blended with powdered pyrophyllite until homogeneous.
  • Test results indicate that compounds of the present invention are highly active preemergent and/or postemergent herbicides or plant growth regulants.
  • vegetation is desired, such as around storage tanks, industrial storage areas, parking lots, drive-in theaters, around billboards, highways, and railroad structures, and in fallow crop areas.
  • crops such as barley (Hordeum spp.), corn (Zea spp.), cotton (Gossypium spp.), pea (Pisum spp.), peanut (Arachis spp.), rape (Brassica spp.), rice (Oryza spp.), sorghum (Sorghum spp.), soybean ( Glycine spp.), sugar beet (Beta spp.), sunflower (Helianthus spp.), triticale (Triticum-Secale spp.), and wheat
  • Triticum spp. Some compounds are particularly useful for preemergence control of troublesome grass and selected small-seeded broadleaf weeds in barley, corn, cotton, rice, soybean, and wheat. In cereal crops such as barley, triticale, and wheat, some compounds are particularly useful for preemergence control of grass weeds such as blackgrass (Alopecurus myosuroides ) , foxtail (Setaria spp.), and wild oat (A ⁇ ena fatua) , and selected broadleaf weeds such as kochia (Kochia scoparia), lambsquarters (Chenopodium album ), and wild buckwheat (Polygonum convolvulus) .
  • grass weeds such as blackgrass (Alopecurus myosuroides ) , foxtail (Setaria spp.), and wild oat (A ⁇ ena fatua)
  • selected broadleaf weeds such as kochia (Kochia scoparia), lambsquarter
  • many compounds of this invention are useful for the control of weeds in plantation crops such as banana, citrus crops, cocoa, coffee, palm, rubber, sugar cane, etc.
  • Several of these compounds are also useful for weed control in fruit crops such as cranberries, apples, pears, cherries, etc.
  • Several compounds of this invention are also useful for weed control in fruit crops such as cranberries, apples, pears, cherries, etc.
  • the subject compounds are useful to modify plant growth.
  • the rates of application for compounds of this invention are determined by a number of factors, including their use as plant growth modifiers or as herbicides, the crop species involved, the types .of weeds to be controlled, weather and climate,
  • the subject compounds should be applied at levels of around 0.004 to 20 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for plant growth modification or for situations where only short-term persistence is required, such as a herbicide for fallow land.
  • Preferred rates of application are from 0.025 to 2.0 kg/ha.
  • One skilled in the art can easily determine the application rate needed for the desired level of weed control.
  • the compounds of the invention may be used in combination with any other commercial herbicide, representative examples of which are those of the sulfonylurea, triazine, triazole, uracil, urea, amide, diphenyl ether, carbamate, imidazolinone, cineole and bipyridylium types.
  • Plants ranged in height from two to eighteen cm (two to three leaf stage) for postemergence treatments.
  • Treated plants and controls were maintained in a greenhouse for approximately sixteen days, after which all species were compared to controls and visually evaluated.
  • the ratings, summarized in Table A, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control.
  • a dash (-) response means no test result.
  • test chemicals preemergence with test chemicals dissolved in a non-phytotoxic solvent.
  • these crop and weed species were also treated with postemergence applications of test chemicals. Plants ranged in height from two to eighteen cm (two to three leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for approximately 24 days, after which all species were compared to controls and visually evaluated.
  • Preemergence and postemergence application rates for each compound are listed in Table B. Plant response ratings, summarized in Table B, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result.
  • Plastic pots were partially filled with silt loam soil. The soil was then saturated with water.
  • Japonica and Indica rice (Oryza sativa ) seedlings at the 2.0 to 2.5 leaf stage, seeds selected from barnyardgrass (Echinochloa crus-galli) , bulrush (Scirpus mucronatus) , duck salad (Heteranthera limosa ) , and umbrella sedge ( Cyperus difformis ) , and sprouted tubers of arrowhead (Sagittaria spp.) and/or waterchestnut (Eleocharis spp.) were planted into this soil.
  • Plant response ratings are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control.
  • blackgrass (Alopecurus myosuroides) , bluegrass (Poa annua) , catchweed bedstraw (Galium aparine) ,
  • cheatgrass (Bromus secalinus), downy brome (Bromus tectorum ) , field pennycress (Thlaspi arvense) , field violet (Viola arvensis), green foxtail (Setaria viridis) , Italian ryegrass (Lolium multiflorum ), ivyleaf
  • Plants ranged in height from two to twenty-four cm (two to three leaf stage) for postemergence treatments.
  • Blackgrass and wild oat were treated postemergence at two growth stages -- the first stage being at two to three leaves and the second stage being approximately at four leaves or in the initial stages of tillering.
  • Treated plants and controls were maintained in a greenhouse for approximately 21 days, after which all species were compared to controls and visually evaluated. Rates of application of each compound are listed in Table D. Plant response ratings, summarized in Table D, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result.
  • test compounds were also applied postemergence to these crop and weed species. For postemergence applications, plants were from two to twenty-five cm tall.
  • Treated plants and controls were maintained in a greenhouse for approximately 24 days, after which all species were compared to controls and visually evaluated. Test rates for each compound are listed in Table G. The ratings, summarized in Table G, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result.
  • Plants ranged in height from four to twenty cm (two to three leaf stage) when
  • Treated plants and controls were grown under greenhouse conditions for approximately twenty-four days, after which all plants treated with the test chemical were compared to untreated controls and visually evaluated for injury response.
  • Application rates for the test chemical are shown in Table I. Plant response ratings, summarized in Table I, are from 0 to 100 where 0 is no injury and 100 is complete control. A dash (-) response means no test result.

Landscapes

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

Abstract

De nouvelles phényltriazolopyrimidines à substitution de la formule (I) dans laquelle G et G1 représentent N ou C; R1 représente halogène, CN ou un groupe organique; R2 représente halogène, NO2 ou un groupe organique; R4 représente H, halogène, ou un groupe organique; R5 représente H, halogène, NO2, CN, ou un groupe organique; R6 représente H ou F; X, Y et Z représentent indépendamment CR7 ou N; et R7 représente H, CN, halogène, NO2 ou un groupe organique; présentent une activité herbicide. On peut notamment les utiliser pour le désherbage sélectif dans les cultures céréalières.
EP89908575A 1988-07-19 1989-07-18 Herbicides a base de phenyltriazolopyrimidine a substitution Pending EP0440659A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US221155 1980-12-29
US22115588A 1988-07-19 1988-07-19
US33512189A 1989-04-07 1989-04-07
US335121 1989-04-07

Publications (1)

Publication Number Publication Date
EP0440659A1 true EP0440659A1 (fr) 1991-08-14

Family

ID=26915548

Family Applications (2)

Application Number Title Priority Date Filing Date
EP89908575A Pending EP0440659A1 (fr) 1988-07-19 1989-07-18 Herbicides a base de phenyltriazolopyrimidine a substitution
EP89307254A Expired - Lifetime EP0353902B1 (fr) 1988-07-19 1989-07-18 Phényltriazolopyrimidines substitués comme herbicides

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP89307254A Expired - Lifetime EP0353902B1 (fr) 1988-07-19 1989-07-18 Phényltriazolopyrimidines substitués comme herbicides

Country Status (9)

Country Link
EP (2) EP0440659A1 (fr)
JP (1) JPH03506033A (fr)
KR (1) KR900701787A (fr)
CN (1) CN1040197A (fr)
AU (1) AU617508B2 (fr)
BR (1) BR8907566A (fr)
DE (1) DE68906324T2 (fr)
ES (1) ES2055073T3 (fr)
WO (1) WO1990001030A1 (fr)

Families Citing this family (18)

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US5110347A (en) * 1990-11-26 1992-05-05 E. I Du Pont De Nemours And Company Substituted fused heterocyclic herbicides
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EP0642512A1 (fr) * 1993-03-25 1995-03-15 Ciba-Geigy Ag Herbicides a base de triazolopyrimidines
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TWI312347B (en) * 2001-02-08 2009-07-21 Eisai R&D Man Co Ltd Bicyclic nitrogen-containing condensed ring compounds
DE20205819U1 (de) * 2002-04-12 2003-08-21 Kinetics Germany GmbH, 63863 Eschau Vorrichtung zur Bereitstellung von hochreinen Prozesschemikalien
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DE68906324T2 (de) 1993-10-21
CN1040197A (zh) 1990-03-07
AU617508B2 (en) 1991-11-28
AU3967789A (en) 1990-02-19
JPH03506033A (ja) 1991-12-26
EP0353902B1 (fr) 1993-05-05
WO1990001030A1 (fr) 1990-02-08
BR8907566A (pt) 1991-06-18
EP0353902A1 (fr) 1990-02-07
ES2055073T3 (es) 1994-08-16
KR900701787A (ko) 1990-12-04
DE68906324D1 (de) 1993-06-09

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