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WO1991010653A1 - Pyrimidines et triazines herbicides - Google Patents

Pyrimidines et triazines herbicides Download PDF

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Publication number
WO1991010653A1
WO1991010653A1 PCT/US1990/007417 US9007417W WO9110653A1 WO 1991010653 A1 WO1991010653 A1 WO 1991010653A1 US 9007417 W US9007417 W US 9007417W WO 9110653 A1 WO9110653 A1 WO 9110653A1
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WO
WIPO (PCT)
Prior art keywords
compound
growth
controlling
effective amount
compresses
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/US1990/007417
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English (en)
Inventor
Steven Powell Artz
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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 WO1991010653A1 publication Critical patent/WO1991010653A1/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
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
    • C07D251/20—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with no nitrogen atoms directly attached to a ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

  • This invention relates to certain herbicidal pyrimidines and triazines, agriculturally suitable compositions thereof and a method for their use as general or selective preemergent or postemergent herbicides or as plant growth regulants.
  • New compounds effective for controlling the growth of undesired vegetation are in constant demand.
  • such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few.
  • Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer.
  • herbicides are desired which will control all plant growth.
  • JP Kokai Hei 1[1989]-301668 discloses mandelic acid derivatives as herbicides:
  • J. Chem. Res.(S) 1977, 186 discloses benzyl pyrimidines as intermediates to herbicides but includes no herbicidal test data for these
  • JP KOKAI HEI 2 [1990] -56469 (unofficial English translation) discloses as herbicides the following structures:
  • Z is CH or N
  • R is a formyl group or CO 2 R 1 ;
  • R 1 is H, lower alkyl, lower alkoxyalkyl or lower alkylthioalkyl.
  • EP-A-360,163 discloses herbicidal compounds of the formula:
  • agriculturally suitable salts agriculturally suitable salts, agricultural
  • compositions containing them and their method-of-use for the control of unwanted weeds both preemergence and postemergence are also present.
  • A is CR 2 , N or N-O
  • X is H, F, Cl, CH 3 , OH, C(O)NR 12 R 13 , CO 2 R 14 or CN;
  • R 1 is H, CHO, C(OCH 3 ) 2 H, CO 2 R 5 or C(O)SR 11 ;
  • R 3 is C 1 -C 2 alkyl, C 1 -C 2 alkoxy, OCF 2 H or Cl;
  • R 4 is C 1 -C 2 alkyl
  • R 5 is H; M; C 1 -C 3 alkyl; C 2 -C 3 haloalkyl;
  • R 6 is H, F, Cl, CH 3 , OCH 3 or S(O) n CH 3 ;
  • R 7 is Cl, C 1 -C 2 alkyl or SCH 3 ;
  • R 8 is C 1 -C 2 alkyl, CO 2 (C 1 -C 2 alkyl) or
  • R 9 is H or CH 3 ;
  • R 10 is C 1 -C 3 alkyl or phenyl optionally
  • R 11 is C 1 -C 2 alkyl or benzyl
  • R 12 is H or CH 3 ;
  • R 13 is H or CH 3 ;
  • n 0, 1 or 2;
  • M is a alkali metal atom or an alkaline earth metal atom, an ammonium group or an alkylammonium group
  • Z is CH or N.
  • alkyl used either alone or in compound words such as
  • R 6 is H
  • R 3 is OCH 3 ;
  • X is H
  • R 6 is H or 3-F
  • R 3 is OCH 3 ;
  • R 14 is C 1 -C 3 alkyl, allyl, propargyl or benzyl; 5.
  • R 1 is CO 2 R 5 ;
  • R 5 is H or M
  • the compounds of this invention are biologically active as herbicides both post and preemergent with selectivity to crops including barley, wheat, corn and cotton.
  • the compounds of Formula I can be prepared by one or more of the following methods described in Eguations 1 to 4.
  • the compounds of Formula I can be prepared by the reaction of an anion, formed from intermediate II and a base, with heterocycle III as shown in
  • Q-1 to Q-6, Z, R 3 and R 4 are as previously
  • R 1 is C(OMe) 2 H
  • X is H.
  • a dry inert solvent such as hexane, benzene, diethyl ether or
  • tetrahydrofuran THF
  • Appropriate bases include hindered amine bases, such as lithium
  • LDA diisopropylamide
  • alkyllithiums such as methyllithium or magnesium salts, such as ethyl magnesium bromide.
  • R 1 contains an acidic group
  • a second equivalent base is required.
  • the reaction can be carried out from low temperatures -78°C (dry ice/acetone) up to the reflux point of the solvent. Generally, a lower temperature is preferred for anion formation, while the coupling of the anion II and III proceeds readily at higher temperatures.
  • R 1 contains an acidic group such as CO 2 H
  • the reaction is extracted into aqueous base, and the water layer acidified.
  • carboxylate can be alkylated in situ to give an alkyl or benzyl ester.
  • the product is either collected by filtration or extracted with an organic solvent and concentrated. The residue is further purified by trituration, crystallization or chromatography in the appropriate solvent. If the R 1 group contains no acidic group, i.e., an isopropylester, then the reaction is quenched with brine, the organic layer separated and concentrated followed by the
  • the compounds of Formula I can be prepared by the reaction of a cyanomethyl derivative IV with heterocycle III as shown in Equation 2a followed by oxidation, then reduction to give the alcohol, which can be converted to the halomethyl derivative (X is F or Cl), or further reduced to the methylene
  • R is equivalent to R 5
  • R 1 is C(OMe) 2 H, Br, CN, CH 2 OSiMe 2 CMe 3 or CO 2 R 5 ;
  • R 5 is H, M, CHMe 2 or CMe 3 ;
  • a and R 6 are as previously defined.
  • Equation 2a wherein Y is Cl, Br, I, CH 3 SO 2 or PhCH 2 SO 2 , is carried out under basic conditions.
  • the starting materials can be premixed in an inert solvent such as diethylether, THF or
  • a strong base such as an alkali metal hydride, i.e., NaH, or a hindered metallated base, i.e., LDA or potassium t-butoxide.
  • Another order of addition for any Y value can be the formation of the anion of acetonitrile IV in an inert solvent, followed by its addition to the heterocycle in an inert solvent. Yields are generally increased with the use of dry solvents and dry inert
  • Diarylketones V can be reduced directly to the diarylmethanes via Equation 2e by Wolff-Kishner conditions as taught by Cram et al., J. Am. Chem.
  • the diarylketones V can also be reduced
  • Equation 2h shows that compounds of Formula I
  • Equation 2i is carried out in a similar fashion to 2a wherein an appropriate base is reacted with the aryl acetate followed by addition of heterocycle III.
  • cyanomethanes and arylacetates of Formula IV are either known in the art or prepared by simple modifications thereof. Cyanomethanes are most conveniently prepared by nucleophilic reaction of a metal cyanide, i.e., NaCN, with a benzyl halide in a suitable solvent, such as dimethylformamide,
  • the compounds of Formula I can be prepared by a cross-coupling reaction between an aryl boronic acid and a bromomethyl heterocycle with a catalyst as shown in Equation 3.
  • T, Z, R 3 and R 4 are as previously defined;
  • R 1 is C(OMe 2 )H, CH 2 OH, CO 2 R 5 or CON(H,CH 3 )- (alkyl, alkylsilyl);
  • R 5 is H, M, isopropyl or t-butyl.
  • the reaction is carried out by mixing the bromide (VII) with a transition metal catalyst, such as Ni(O) or Pd(O), preferably Pd(PPh 3 ) 4 in a suitable solvent, such as toluene or glyme, followed by the addition of boronic acid VI and the base, such as an alkoxide, hydroxide or carbonate, for example NaOEt, NaOH or Na 2 CO 3 in a suitable solvent such as water or ethanol.
  • a suitable solvent such as toluene or glyme
  • boronic acid VI and the base such as an alkoxide, hydroxide or carbonate, for example NaOEt, NaOH or Na 2 CO 3 in a suitable solvent such as water or ethanol.
  • the reaction mixture is stirred from 1 to 24 hours at room temperature to reflux.
  • Bromomethanes VII can be prepared by well known methods for conversion from alcohols and from methyl groups. A representative example is described in
  • the reaction is carried out by reacting IV with hydrogen chloride in an alcohol to form an imidate which is converted to the amidine salt, VIII, with ammonia.
  • the pyrimidinol IX is formed by
  • Heterocycles of Formula III are generally known in the art or can be prepared by simple modifications thereof.
  • preparation of chlorotriazines is described in J . Am. Chem. Soc . , 1951 , 73, 2989, while chloropyrimidines are described in J. Chem. Soc. (C), 1966, 2031.
  • alkylsulfonyl and benzylsulfonyl heterocycles can also be prepared by the general reference above and more specifically by alkylation of thiols, as described in J. Med. Chem., 1984, 27, 1621-1629, followed by oxidation, most commonly by m-chloroperoxybenzoic acid.
  • R 1 groups of Equations 1 to 4 can be converted into the claimed R 1 groups by techniques well known to one skilled in the art.
  • benzyl alcohols can be oxidized to aldehydes with many reagents, including pyridinium chlorochromate (PCC) and/or further oxidized to the carboxylate with potassium permanganate (KMnO 4 ).
  • PCC pyridinium chlorochromate
  • KMnO 4 potassium permanganate
  • the base may be an alkali metal such as sodium metal or potassium metal, an alkali metal or alkaline earth metal hydride such as sodium hydride, potassium hydride or calcium hydride, a carbonate such as sodium carbonate, potassium
  • the organic base may be ammonia, an alkylamine (primary amine), a dialkylamine (secondary amine) or a
  • trialkylamine (tertiary amine).
  • 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
  • Active ingredient plus at least one of a
  • Surfactant or a Diluent equals 100 weight percent Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.
  • 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
  • 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.
  • Example G The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.
  • Example G The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.
  • Example G The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.
  • 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.
  • Example I The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.
  • the active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then 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 a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening).
  • the concentrate may be formulated further if necessary.
  • Example O 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.
  • Example O 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 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.
  • a herbicidally effective amount of the compounds of the invention is applied at rates from 0.004 to 20 kg/ha with a preferred rate range of 0.025 to 2 kg/ha.
  • 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
  • Herbicidal properties of the compounds that follow were determined in greenhouse tests. Test results and procedures follow.
  • soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (AbutiIon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avena fatua) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated with
  • barnyardgrass Echinochloa crus-galli
  • blackgrass Alopecurus myosuroides
  • chickweed Stellaria media
  • cocklebur Xanthium pensylvanicum
  • corn Zea mays
  • cotton Gossypium hirsutum
  • crabgrass Echinochloa crus-galli
  • blackgrass Alopecurus myosuroides
  • chickweed Stellaria media
  • cocklebur Xanthium pensylvanicum
  • corn Zea mays
  • cotton Gossypium hirsutum
  • crabgrass Echinochloa crus-galli
  • blackgrass Alopecurus myosuroides
  • chickweed Stellaria media
  • cocklebur Xanthium pensylvanicum
  • corn Zea mays
  • cotton Gossypium hirsutum
  • Croperus rotundus tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. At the same time, 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 eighteen to twenty-four days, after which all species were compared to controls and visually evaluated. Plant response ratings,
  • preemergence application to water that covered the soil surface
  • postemergence application to plants that were in the one-to-four leaf stage
  • a sandy loam soil was used for the preemergence and postemergence tests, while a silt loam soil was used in the paddy test. Water depth was approximately 2.5 cm for the paddy test and was maintained at this level for the duration of the test.
  • Plantings of these species were adjusted to produce plants of appropriate size for the postemergence portion of the test.
  • Plant species in the paddy test consisted of barnyardgrass (Echinochloa crus-galli), rice (Oryza sativa), and umbrella sedge (Cyperus difformis). All plant species were grown using normal greenhouse practices. Visual evaluations of injury expressed on treated plants, when compared to

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth 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)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Cette invention concerne certaines triazines et pyrimidines de sulfonylurée herbicides, utiles pour le désherbage total et/ou sélectif, la sélectivité étant importante pour les cultures agricoles.
PCT/US1990/007417 1990-01-11 1990-12-27 Pyrimidines et triazines herbicides Ceased WO1991010653A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US46335690A 1990-01-11 1990-01-11
US463,356 1990-01-11
US54239090A 1990-06-22 1990-06-22
US542,390 1990-06-22

Publications (1)

Publication Number Publication Date
WO1991010653A1 true WO1991010653A1 (fr) 1991-07-25

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Cited By (20)

* Cited by examiner, † Cited by third party
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EP0461079A3 (en) * 1990-06-07 1992-03-04 Sandoz Ltd. Substituted phthalides and heterocyclic phthalides
WO1993009099A3 (fr) * 1991-11-07 1993-06-10 Schering Agrochemicals Ltd Herbicides contenant des sulfonamides
EP0549524A1 (fr) * 1991-12-06 1993-06-30 Sandoz Ltd. Phthalides substitués et phthalides hétérocycliques et leur usage en agriculture
EP0567133A1 (fr) * 1992-04-23 1993-10-27 Kumiai Chemical Industry Co., Ltd. Dérivés de l'acide picolinique et compositions herbicides
US5403816A (en) * 1990-10-25 1995-04-04 Kumiai Chemical Industry Co., Ltd. Picolinic acid derivative and herbicidal composition
US5561101A (en) * 1990-06-07 1996-10-01 Sandoz Ltd. Substituted phthalides and heterocyclic phthalides
WO1996041799A1 (fr) * 1995-06-12 1996-12-27 Hoechst Schering Agrevo Gmbh Sulfonamides utilises comme herbicides et comme regulateurs de croissance vegetale
US5716901A (en) * 1993-02-18 1998-02-10 Sandoz Ltd. Synergistic herbicidal compositions of dimethenamid, sulcotrione, and atrazine
US5721191A (en) * 1993-02-18 1998-02-24 Sandoz Ltd. Synergistic herbicidal compositions of dimethenamid and sulfonylureas
US5877117A (en) * 1988-12-29 1999-03-02 Anderson; Richard J. Potentiating herbicidal compositions of auxin transport inhibitors and quinclorac
US5877115A (en) * 1993-02-18 1999-03-02 Sandoz Ltd. Dicamba and dimethenamid synergistic herbicidal compositions
US5888936A (en) * 1993-02-18 1999-03-30 Sandoz Ltd. Synergistic herbicidal compositions of dimethenamid and phenmedipham
RU2133746C1 (ru) * 1994-03-22 1999-07-27 Кумиай Кемикал Индастри Ко., Лтд. Производные никотиновой кислоты, способ их получения и гербицидная композиция
US5977024A (en) * 1997-11-03 1999-11-02 Basf Corporation Mixtures and methods for suppressing precipitation of chloroacetamides
US6107248A (en) * 1988-12-29 2000-08-22 Anderson; Richard J. Potentiating herbicidal compositions of auxin transport inhibitors and growth regulators
US6428814B1 (en) 1999-10-08 2002-08-06 Elan Pharma International Ltd. Bioadhesive nanoparticulate compositions having cationic surface stabilizers
RU2266904C2 (ru) * 1992-07-07 2005-12-27 Агрево Ю-кей Лимитед Производные сульфонамидов, способ их получения, композиция и способ уничтожения сорняков
US7459283B2 (en) 2002-02-04 2008-12-02 Elan Pharma International Limited Nanoparticulate compositions having lysozyme as a surface stabilizer
EP2050338A1 (fr) 1993-02-18 2009-04-22 Basf Se Compositions herbicides
US8754228B2 (en) 2011-11-16 2014-06-17 Paresh T. Gandhi Nicotine derivatives

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9105297D0 (en) * 1991-03-13 1991-04-24 Schering Agrochemicals Ltd Herbicides

Citations (3)

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US5888937A (en) * 1988-12-29 1999-03-30 Anderson; Richard J. Potentiating herbicidal compositions of auxin transport inhibitors and phenoxy butyric acid herbicides
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US5403816A (en) * 1990-10-25 1995-04-04 Kumiai Chemical Industry Co., Ltd. Picolinic acid derivative and herbicidal composition
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EP0549524A1 (fr) * 1991-12-06 1993-06-30 Sandoz Ltd. Phthalides substitués et phthalides hétérocycliques et leur usage en agriculture
EP0567133A1 (fr) * 1992-04-23 1993-10-27 Kumiai Chemical Industry Co., Ltd. Dérivés de l'acide picolinique et compositions herbicides
RU2266904C2 (ru) * 1992-07-07 2005-12-27 Агрево Ю-кей Лимитед Производные сульфонамидов, способ их получения, композиция и способ уничтожения сорняков
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US5900389A (en) * 1993-02-18 1999-05-04 Fenderson; John M. Synergistic herbicidal compositions of dimethenamid and urea herbicidies
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US5888936A (en) * 1993-02-18 1999-03-30 Sandoz Ltd. Synergistic herbicidal compositions of dimethenamid and phenmedipham
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US5908809A (en) * 1993-02-18 1999-06-01 Fenderson; John M. Synergistic herbicidal compositions of dimethenamid and uracil herbicides
US5895773A (en) * 1993-02-18 1999-04-20 Fenderson; John M. Herbicidal compositions comprising dimethenamid and a pyridazinone herbicide
US5922643A (en) * 1993-02-18 1999-07-13 Sandoz Ltd. Herbicidal compositions comprising dimethenamid and aryloxyphenoxy herbicides
EP2050338A1 (fr) 1993-02-18 2009-04-22 Basf Se Compositions herbicides
US5928996A (en) * 1993-02-18 1999-07-27 Sandoz Ltd. Synergistic herbicidal compositions of dimethenamid and dinitroaniline herbicides
EP2272342A2 (fr) 1993-02-18 2011-01-12 Basf Se Compositions herbicides
US5990046A (en) * 1993-02-18 1999-11-23 Sandoz Ltd. Herbicidal compositions comprising dimethenamid and diketone or triketone herbicides
US5877115A (en) * 1993-02-18 1999-03-02 Sandoz Ltd. Dicamba and dimethenamid synergistic herbicidal compositions
US5721191A (en) * 1993-02-18 1998-02-24 Sandoz Ltd. Synergistic herbicidal compositions of dimethenamid and sulfonylureas
US5716901A (en) * 1993-02-18 1998-02-10 Sandoz Ltd. Synergistic herbicidal compositions of dimethenamid, sulcotrione, and atrazine
RU2133746C1 (ru) * 1994-03-22 1999-07-27 Кумиай Кемикал Индастри Ко., Лтд. Производные никотиновой кислоты, способ их получения и гербицидная композиция
WO1996041799A1 (fr) * 1995-06-12 1996-12-27 Hoechst Schering Agrevo Gmbh Sulfonamides utilises comme herbicides et comme regulateurs de croissance vegetale
US5977024A (en) * 1997-11-03 1999-11-02 Basf Corporation Mixtures and methods for suppressing precipitation of chloroacetamides
US7288267B2 (en) 1999-10-08 2007-10-30 Elan Pharma International Ltd. Bioadhesive nanoparticulate compositions having cationic surface stabilizers
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