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WO1990012012A1 - Herbicides de phenyltriazolopyrimidines substituees - Google Patents

Herbicides de phenyltriazolopyrimidines substituees Download PDF

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Publication number
WO1990012012A1
WO1990012012A1 PCT/US1990/000152 US9000152W WO9012012A1 WO 1990012012 A1 WO1990012012 A1 WO 1990012012A1 US 9000152 W US9000152 W US 9000152W WO 9012012 A1 WO9012012 A1 WO 9012012A1
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WO
WIPO (PCT)
Prior art keywords
och
chf
methyl
ocf
compound
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.)
Ceased
Application number
PCT/US1990/000152
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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 WO1990012012A1 publication Critical patent/WO1990012012A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • 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
    • 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

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 ;
  • 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
  • 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,.
  • n 0, 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- ⁇ ropenyl, 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-halogenated 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 Ia); 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 ;
  • X is N
  • Y is CR 7 ;
  • 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, CCl 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 1 -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 1 -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 Ia 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 Ia directly from the crude reaction residue obtained after reaction work up.
  • Scheme-2 illustrates the preparation of compounds of Formula Ia (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.
  • 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, micro- biological 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 hammermilled 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,
  • 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) , lambsquarters
  • some compounds are particularly useful for the control of barnyardgrass (Echinochloa crus-galli) .
  • Utility in rice includes, but is not limited to, upland rice and both direct-seeded and paddy rice.
  • cotton some compounds are particularly useful for the control of barnyardgrass (Echinochloa crus-galli), bermudagrass
  • 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.
  • a partial listing follows: Common Name Chemical Name
  • DPX-M6316 3-[[[[[(4-methoxy-6-methyl-1,3,5-triazin- 2-yl)amino]carbonyl]amino]sulfonyl]- 2-thiophenecarboxylic acid, methyl ester
  • paraquat 1,1'-dimethyl-4,4'-dipyridinium ion pebulate S-propyl butylethylcarbamothioate pendimethalin N-(1-ethylpropyl)-3,4-dimethyl-2,6- dinitrobenzenamine
  • PPG-1013 5-[2-chloro-4-(trifluoromethyl)- phenoxy]-2-nitroacetophenone
  • 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.
  • Plastic pots were partially filled with silt loam soil. The soil was then saturated with water.
  • Indica and Japonica rice (Oryza sati ⁇ a) 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 waterchestnut
  • 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
  • Table D 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.
  • Treated plants and controls were maintained in a greenhouse for approximately 21 days, after which all species were compared to controls and visually evaluated.
  • Response ratings summarized in Table F, 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.
  • 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
  • a dash (-) response means no test result.
  • Plants ranged in height from four to twenty cm (two to three leaf stage) when

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

Abstract

L'invention concerne de nouvelles phényltriazolopyrimidines substituées de la formule (I), dans laquelle G et G1 représentent N ou C; R¿1? représente halogène, NO2 ou un groupe organique; R4 représente halogène, NO2 ou un groupe organique; R4 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; ces nouvelles phenyltriazolopyrimidines présentant une activité herbicide. On peut les utiliser inter alia dans la régulation sélective de mauvaises herbes dans les cultures céréalières.
PCT/US1990/000152 1989-04-07 1990-01-17 Herbicides de phenyltriazolopyrimidines substituees Ceased WO1990012012A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US33512189A 1989-04-07 1989-04-07
US335,121 1989-04-07
USPCT/US89/03039 1989-07-18

Publications (1)

Publication Number Publication Date
WO1990012012A1 true WO1990012012A1 (fr) 1990-10-18

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994021640A1 (fr) * 1993-03-25 1994-09-29 Ciba-Geigy Ag Herbicides a base de triazolopyrimidines

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4178449A (en) * 1978-04-17 1979-12-11 American Cyanamid Company Pyrazolo[1,5-a]pyrimidines and imidazo-[1,5-a]pyrimidines
EP0142152A2 (fr) * 1983-11-14 1985-05-22 The Dow Chemical Company 1,2,4-Triazolo[1,5-a]pyrimidine sulfonamides et compositions et méthodes pour contrôler la végétation non-désirable et supprimer la nitrification d'azote ammonium du sol
EP0244097A2 (fr) * 1986-04-30 1987-11-04 Schering Agrochemicals Limited Herbicides de pyrazolopyrimidine

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4178449A (en) * 1978-04-17 1979-12-11 American Cyanamid Company Pyrazolo[1,5-a]pyrimidines and imidazo-[1,5-a]pyrimidines
EP0142152A2 (fr) * 1983-11-14 1985-05-22 The Dow Chemical Company 1,2,4-Triazolo[1,5-a]pyrimidine sulfonamides et compositions et méthodes pour contrôler la végétation non-désirable et supprimer la nitrification d'azote ammonium du sol
EP0244097A2 (fr) * 1986-04-30 1987-11-04 Schering Agrochemicals Limited Herbicides de pyrazolopyrimidine

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Vol. 58, No. 8, 15 April 1963, (Columbus, Ohio, US), W. RIED et al.: "Syntheses and Reactions of Pyrazolo (1,5-a)Pyrimidines. II.", * see column 9075a, & Ann. 660, 104-17 (1962); cf. CA 56, 7317b* *
CHEMICAL ABSTRACTS, Vol. 83, No. 15, 13 October 1975, (Columbus, Ohio, US), T. OKABE et al.: "Biological Activities of 1,3,4-Thiadiazolo(3,2-a)Pyrimidines and s-Triazolo(1,5-a)Pyrimidines", see pages 140-141* Abstract 127285r & J. Fac. Agric. Kyushu Univ. 1975, 19(2-3), 91-102* *
CHEMICAL ABSTRACTS, Vol. 87, No. 3, 18 July 1977, (Columbus, Ohio, US), K. MAZUYUKI et al.: "Control of Seedling Growth by Pseudopurine Pyrimidine Derivatives", see page 153* Abstract 17148Y & J. Fac. Agric., Kyushu Univ. 1977, 21(2-3), 99-105* *
Chemische Berichte, Vol. 95, No. 9, 1962, Verlag Chemie GmbH, (Weinheim, DE), R. GOMPPER et al.: "Pyrazole und Isoxazole aus Ketenmercaptalen", pages 2881-2884 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994021640A1 (fr) * 1993-03-25 1994-09-29 Ciba-Geigy Ag Herbicides a base de triazolopyrimidines

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