WO2001094339A1 - Substituted pyridine herbicides - Google Patents
Substituted pyridine herbicides Download PDFInfo
- Publication number
- WO2001094339A1 WO2001094339A1 PCT/EP2001/006430 EP0106430W WO0194339A1 WO 2001094339 A1 WO2001094339 A1 WO 2001094339A1 EP 0106430 W EP0106430 W EP 0106430W WO 0194339 A1 WO0194339 A1 WO 0194339A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- alkoxy
- formula
- crc
- halogen
- Prior art date
Links
- 0 Cc1c(*)[n](C)nc1C Chemical compound Cc1c(*)[n](C)nc1C 0.000 description 16
- ABDKAPXRBAPSQN-UHFFFAOYSA-N COc1ccccc1OC Chemical compound COc1ccccc1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N C1CCOCC1 Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- RTLAJYPVXKNGFV-UHFFFAOYSA-N CC#Cc1ccccc1OC Chemical compound CC#Cc1ccccc1OC RTLAJYPVXKNGFV-UHFFFAOYSA-N 0.000 description 1
- PKNQRTZIRVEJAU-UHFFFAOYSA-N COCCOCCOCCOCc1nc(C(F)(F)F)ccc1C(C(C(C1CC2CC1)=O)=C2O)=O Chemical compound COCCOCCOCCOCc1nc(C(F)(F)F)ccc1C(C(C(C1CC2CC1)=O)=C2O)=O PKNQRTZIRVEJAU-UHFFFAOYSA-N 0.000 description 1
- QAFBMWOMWTUAOI-UHFFFAOYSA-N OC(C1CC2CC1)C(C(C(CCC(C(F)(F)F)N1)C1OC1COC1)=O)C2=O Chemical compound OC(C1CC2CC1)C(C(C(CCC(C(F)(F)F)N1)C1OC1COC1)=O)C2=O QAFBMWOMWTUAOI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Definitions
- the present invention relates to novel herbicidally active pyridine ketones, to processes for their preparation, to compositions which comprise these compounds, and to their use for controlling weeds, in particular in crops of useful plants, or for inhibiting plant growth.
- R 2 is a C ⁇ C 8 alkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl group which is mono- or polysubstituted by halogen, hydroxyl, amino, formyl, nitro, cyano, mercapto, carbamoyl, d-Cealkoxy,
- R 5 is hydroxyl, C C 6 alkoxy, C 3 -C 6 cycloalkyloxy, CrCealkoxy-C Cealkoxy,
- R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R5 1 and R 52 independently of one another are hydrogen,
- R 15 and R 2 ⁇ independently of one another are hydrogen, d-C 4 alkyl, d-C 4 haloalkyl,
- C 2 -C 4 alkylene chain which may be interrupted by oxygen and/or carbonyl and/or sulfur, with the proviso that the oxygen and sulfur atoms are separated by at least one methylene group; or R 14 and R 18 together form a C 2 -C 4 alkylene chain; or
- R 22 and R 18 together form a C 2 -C 4 alkylene chain; or R 18 together with R 22 or R 14 forms a direct bond; or R 16 and R ⁇ 8 together form a C 2 -C 4 alkylene chain;
- R 13 is hydroxyl, O " M ⁇ where M + is an alkali metal cation or ammonium cation, halogen, d-C 12 alkylsulfonyloxy, amino, C C 4 alkylthio, d-C ⁇ 2 alkylsulfinyl, d-C 12 alkylsulfonyl,
- R 29 R 30 NC(O)NH-, C C 18 alkylcarbonyloxy, C 2 -C ⁇ 8 alkenylcarbonyloxy, C 2 -C 18 alkynyl- carbonyloxy, C 3 -C 6 cycloalkylcarbonyloxy, d-C ⁇ 2 alkoxycarbonyloxy, d-C 12 alkylthio- carbonyloxy, d-C ⁇ 2 alkylthiocarbamoyl, where the alkyl, alkenyl and alkynyl groups may be substituted by halogen, d-C 6 alkoxy, d-C 6 alkylthio, d-C 6 alkylsulfinyl, CrC 6 alkylsulfonyl or cyano; or R 13 is phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonylamino, phenylsul
- Het-i, Het 2 , Het 3 , Het 4 and Het 5 independently of one another are a five- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic or partially saturated and may contain 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and where each ring system may not contain more than 2 oxygen atoms and not more than 2 sulfur atoms, and where the ring system itself can be substituted by d-C 6 alkyl, d-Cehaloalkyl, C C 6 alkoxy, d-C 6 haloalkoxy, d-C 6 alkylthio, d-C 6 alkylsulfinyl, C C 6 alkyl- sulfonyl, di(C -C alkyl)aminosulfonyl, di(C 1 -C 4 alkyl)amino, halogen, cyano, nitro or phenyl, and where the substituents on
- R25, 26, R27, 28, R29, R30 and R 33 independently of one another are hydrogen or d-C 6 alkyl; or
- R 2 3 and R 24 together or R 25 and R 26 together or R 27 and R 28 together or R 29 and R 30 together are pyrolidino, piperidino, morpholino, thiomorphoiino, which may be mono- or polysubstituted by methyl groups; or Q is Q 2
- R 3 is hydrogen, d-C 4 alkyl, C C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl or benzyl, where the phenyl group may be mono- or polysubstituted by d-C 6 alkyl, d-C 6 halo- alkyl, C C 6 alkoxy, C-
- R 35 is hydrogen, C ⁇ -C 4 alkyl, C C 4 haIoalkyl, C 3 -C 6 cycloalkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl or benzyl, where the phenyl group may be mono- or polysubstituted by C ⁇ -C 6 alkyl, d-C 6 halo- alkyl, d-C 6
- R 36 is phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylsulfonylamino, phenylsulfonyloxy or benzoyloxy, where the phenyl groups for their part may be mono- or polysubstituted by halogen, nitro, cyano, d-C alkyl, d-C 4 haloalkyl, C- ⁇ -C 4 alkoxy, C C 4 halo- alkoxy, or R 36 is a group Het 7 -thio, Het 8 -sulfinyl, Het 9 -sulfonyl, Het 10 -(CO)O or Het ⁇ N(R 47 ); in which Het 7 , Het 8 , Het 9 , Het 10 and Het ⁇ independently of one another are a five- to ten-membered monocyclic or fused bicyclic ring system which may
- HaloalkyI groups preferably have a chain length of from 1 to 6 carbon atoms.
- Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1 ,1 -difluoro- 2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl; preferably trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and dichlorofluoromethyl.
- Alkoxy groups preferably have a chain length of from 1 to 6 carbon atoms.
- Alkoxy is, for example, methoxy, ethoxy, propoxy, i-propoxy, n-butoxy, isobutoxy, sec-butoxy and tert- butoxy and also the isomeric pentyloxy and hexyloxy radicals; preferably methoxy and ethoxy.
- Alkylcarbonyl is preferably acetyl or propionyl.
- Alkylthio is, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, preferably methylthio and ethylthio.
- alkoxyalkoxy groups are: methoxymethoxy, methoxyethoxy, methoxypropoxy, ethoxymethoxy, ethoxyethoxy, propoxymethoxy or butoxybutoxy.
- Alkylamino is, for example, methylamino, ethylamino, n-propylamino, isopropylamino or the isomeric butylamines.
- Dialkylamino is, for example, dimethylamino, methylethylamino, diethylamino, n-propylmethylamino, dibutylamino and diisopropylamino.
- Phenyl also as part of a substituent such as phenoxy, benzyl, benzyloxy, benzoyl, phenylthio, phenylalkyl, phenoxyalkyl, may be substituted.
- the substituents can be in ortho, meta and/or para position.
- the preferred substituent positions are the ortho and para positions to the ring attachment point.
- Preferred quartemary ammonium bases which are suitable for salt formation correspond, for example, to the formula [N(R a RbRcRa )]OH, in which R a , R b , Re and R d independently of one another are C- ⁇ -C 4 alkyl.
- R a , R b , Re and R d independently of one another are C- ⁇ -C 4 alkyl.
- Other suitable tetraalkylammonium bases with other anions can be obtained, for example, by anion exchange reactions.
- R51 and R 52 independently of one another are in particular hydrogen, d-C 4 alkyl, CrCealkoxy-d-Cealkyl or d-Cealkoxy-C Cealkyl which is substituted by d-C 6 alkoxy, where in a preferred group of compounds of the formula I additionally Q is Q 2 and Ri is methylene.
- the isomerization of the ester derivatives of the formulae Ilia, lllb and lllc to derivatives of the formula I (in which R 13 and R 36 are hydroxyl) can be carried out, for example, similarly to EP-A-0 353 187, EP-A-0 316 491 or WO 97/46530 in the presence of a base such as an alkylamine, for example triethylamine, a carbonate, for example potassium carbonate, and a catalytic amount of DMAP or a source of cyanide, such as acetone cyanohydrin or potassium cyanide.
- a base such as an alkylamine, for example triethylamine
- a carbonate for example potassium carbonate
- a catalytic amount of DMAP or a source of cyanide such as acetone cyanohydrin or potassium cyanide.
- amide for example N,N-dimethylformamide (DMF), a sulfoxide, for example dimethyl sulfoxide (DMSO), or a nitrile, for example acetonitrile.
- the ketene thioacetal of the formula VI that is formed is cyclized with the aid of hydroxylamine hydrochloride in the presence of a base such as sodium acetate in a solvent such as an alcohol, for example ethanol, or an ether, for example tetrahydrofuran, to give the isomeric compounds of the formulae Ic and Id (in which n is 0). This cyclization reaction is carried out at temperatures of from 0°C to 100°C.
- R g is as defined under formula I and M + is an alkali metal ion (cf., for example, WO 96/26192).
- R 01 H, C C 4 alkyl
- the starting materials used are, for example, appropriately substituted amines, or hydroxylamines directly, or alkylsulfonamides, mercaptans, thiophenols, phenols, heterocyclic amines or heterocyclic thiols in the presence of a base, for example 5-ethyl-2-methylpyridine, diisopropylethylamine, triethylamine, sodium bicarbonate, sodium acetate or potassium carbonate.
- a base for example 5-ethyl-2-methylpyridine, diisopropylethylamine, triethylamine, sodium bicarbonate, sodium acetate or potassium carbonate.
- the compounds of the formulae I) and lla are known and can be prepared similarly as described, for example, in WO 92/07837, JP 10265441 , DE-A-3818958, EP-A-0 338 992, DE-A-3902818, EP-A-0 278 742, WO 98/29412, JP 02059566, US-A-5,089,046, GB-A- 2205316, WO 00/27821 or EP-A-0 384 736.
- the required intermediates of the formula lb are synthesized similarly to known processes as described, for example, in WO 00/15615, WO/00/39094 or WO 97/46530, or they can be prepared for example, according to generally known conversion methods such as the Stille (see, for example Angew. Chem. 1986, 98(6), 504- 19), Heck (see, for example, Angew. Chem. 1994, 106 (23/24), 2473-506), Sonogashira (see, for example, "Comprehensive Organometallic Synthesis", Pergamon Verlag, Oxford, Vol 3, 1991, page 521 ff.) or Wittig (for example C.
- Stille see, for example Angew. Chem. 1986, 98(6), 504- 19
- Heck see, for example, Angew. Chem. 1994, 106 (23/24), 2473-506
- Sonogashira see, for example, "Comprehensive Organometallic Synthesis", Pergamon Verlag, Oxford, Vol 3,
- aprotic inert organic solvents are hydrocarbons such as benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons such as dichloromethane, trichloromethane, tetrachloromethane or chlorobenzene, ethers such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane, nitriles such as acetonitrile or propionitrile, amides such as N,N-dimethylformamide, diethylformamide or N-methylpyrrolidinone.
- hydrocarbons such as benzene, toluene, xylene or cyclohexane
- chlorinated hydrocarbons such as dichloromethane, trichloromethane, tetrachloromethane or chlorobenzene
- ethers such as diethyl
- reaction temperatures are advantageously between -20°C and +120°C.
- the reactions are slightly exothermic and, as a rule, they can be carried out at room temperature.
- the mixture may be heated briefly to the boiling point of the reaction mixture.
- the reaction times can also be shortened by adding a few drops of base as reaction catalyst.
- the compounds of the formula I can be isolated in the customary manner by concentrating and/or by evaporating the solvent and purified by recrystallization or trituration of the solid residue in solvents in which they are not readily soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons.
- the compounds of the formula I can be employed as herbicides as such, i.e. as obtained from synthesis. However, they are preferably processed in the customary manner together with the auxiliaries conventionally used in the art of formulation, for example to give emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcapsules.
- auxiliaries conventionally used in the art of formulation, for example to give emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcapsules.
- Such formulations are described, for example, in WO 97/34485 on pages 9 to 13.
- the application methods such as spraying, atomizing, dusting, wetting, scattering or pouring, as well as the type of composition, are chosen to suit the intended aims and the prevailing
- compositions, preparations or products which comprise the active ingredient of the formula I or at least one active ingredient of the formula I and, as a rule, one or more solid or liquid formulation auxiliaries are prepared in the known manner, for example by intimately mixing and/or grinding the active ingredients together with the formulation auxiliaries, for example solvents or solid carriers.
- formulation auxiliaries for example solvents or solid carriers.
- surface-active compounds surfactants
- solvents and solid carriers are indicated for example in WO 97/34485 on page 6.
- Suitable surface-active compounds are, depending on the nature of the active ingredient of the formula I to be formulated, nonionic, cationic and/or anionic surfactants and surfactant mixtures which have good emulsifying, dispersing and wetting properties.
- suitable anionic, nonionic and cationic surfactants are enumerated, for example, in WO 97/34485 on pages 7 and 8.
- the herbicidal formulations comprise 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of herbicide, 1 to 99.9% by weight, in particular 5 to 99.8% by weight, of a solid or liquid formulation auxiliary and 0 to 25% by weight, in particular 0.1 to 25% by weight, of a surfactant.
- concentrated compositions are more preferred as commercially available goods, the end consumer uses, as a rule, dilute compositions.
- the compositions can also comprise further additives such as stabilizers, for example epoxidized or non-epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soya oil), antifoams, e.g. silicone oil, preservatives, viscosity regulators, binders, tackifiers and fertilizers or other active ingredients.
- the active ingredients of the formula I are applied to the plant or its environment at rates of 0.001 to 4 kg/ha, in particular 0.005 to 2 kg/ha.
- the dosage required for the desired action can be determined by experiments. It depends on the type of the action, the developmental stage of the crop plant and of the weed, and on the application (location, timing, method) and can, owing to these parameters, vary within wide limits.
- the compounds of the formula I are distinguished by herbicidal and growth-inhibitory properties which allow them to be employed in crops of useful plants, in particular in cereals, cotton, soya, sugar beet, sugar cane, plantation crops, rapeseed, maize and rice and for the non-selective control of weeds.
- Crops are also to be understood as including those which have been rendered tolerant to herbicides or classes of herbicides by means of conventional plant-breeding or genetic-engineering methods.
- the weeds to be controlled may be both mono- and dicotyledonous weeds such as Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica.
- Stellaria Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium
- Example H3 4-Hvdroxy-3-f2-(2-methoxyethoxymethyl)-6-trifluoromethylpyridine-3-carbonvn- bicyclof3.2.1 loct-3-en-2-one:
- the viscous oil obtained by eluting with a mixture of toluene, ethyl alcohol, dioxane, triethylamine and water (100:40:20:20:5 parts by volume) is dissolved in ethyl acetate and washed successively with 10% hydrochloric acid and water.
- the organic solution is dried over Na 2 SO 4 and concentrated, giving 2.14 g (38%) of pure 3-(2-hydroxy-4-oxobicyclo[3.2.1]oct-2-ene-3- carbonyl)-6-trifluoromethylpyridin-2-ylmethyl acetate in the form of an oil.
- Example H5 4-Hvdroxy-3-(2-oxiranylmethoxymethyl-6-trifluoromethylpyridine-3-carbonyl)- bicyclo[3.2.1 loct-3-en-2-one:
- Example H6 (5-Hydroxy-1 ,3-dimethyl-1 H-pyrazol-4-yl)-
- the reaction solution is stirred at room temperature for four hours and then concentrated.
- the syrup that remains is chromatographed on silica gel.
- the viscous oil obtained by eluting with a mixture of toluene, ethyl alcohol, dioxane, triethylamine and water (100:40:20:20:5 parts by volume) is dissolved in ethyl acetate and washed successively with 10% hydrochloric acid and water.
- A423 CH CHCH 2 r -CH, H CF 3 O 0
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims
Priority Applications (19)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PL358807A PL216038B1 (en) | 2000-06-09 | 2001-06-07 | Substituted pyridine herbicides |
AU2001262344A AU2001262344B2 (en) | 2000-06-09 | 2001-06-07 | Substituted pyridine herbicides |
US10/297,685 US6838564B2 (en) | 2000-06-09 | 2001-06-07 | Substituted pyridine herbicides |
HU0301243A HU228428B1 (en) | 2000-06-09 | 2001-06-07 | Substituted pyridine herbicides |
DE60120964T DE60120964T2 (en) | 2000-06-09 | 2001-06-07 | SUBSTITUTED PYRIDINES WITH HERBICIDAL EFFECT |
EP01936439A EP1286985B1 (en) | 2000-06-09 | 2001-06-07 | Substituted pyridine herbicides |
MXPA02011977 MX244506B (en) | 2000-06-09 | 2001-06-07 | Substituted pyridine herbicides. |
SK1723-2002A SK287483B6 (en) | 2000-06-09 | 2001-06-07 | Substituted pyridines, method for their preparation, herbicidal and plant growth regulating composition, and their use |
CA2410345A CA2410345C (en) | 2000-06-09 | 2001-06-07 | Substituted pyridine herbicides |
JP2002501888A JP4965050B2 (en) | 2000-06-09 | 2001-06-07 | Substituted pyridine herbicides |
ROA200201526A RO122034B1 (en) | 2000-06-09 | 2001-06-07 | Substituted pyridines to be used as herbicides |
BRPI0111981-8A BR0111981B1 (en) | 2000-06-09 | 2001-06-07 | substituted pyridine herbicides, process for their preparation, herbicidal composition and plant growth inhibitor and processes for controlling and inhibiting plant growth. |
AU6234401A AU6234401A (en) | 2000-06-09 | 2001-06-07 | Substituted pyridine herbicides |
UA2003010242A UA74191C2 (en) | 2000-06-09 | 2001-07-06 | Substituted pyridines as herbicides and intermediary products |
HR20020969A HRP20020969B1 (en) | 2000-06-09 | 2002-12-06 | Substituted pyridine herbicides |
HK03105194.0A HK1054376B (en) | 2000-06-09 | 2003-07-17 | Substituted pyridine herbicides |
US10/893,792 US7378375B1 (en) | 2000-06-09 | 2004-07-16 | Substituted pyridine herbicides |
US12/126,238 US7691785B2 (en) | 2000-06-09 | 2008-05-23 | Substituted pyridine herbicides |
HR20080664A HRP20080664A2 (en) | 2000-06-09 | 2008-12-19 | Substituted pyridine herbicides |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH11512000 | 2000-06-09 | ||
CH1151/00 | 2000-06-09 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10297685 A-371-Of-International | 2001-06-07 | ||
US10/893,792 Division US7378375B1 (en) | 2000-06-09 | 2004-07-16 | Substituted pyridine herbicides |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001094339A1 true WO2001094339A1 (en) | 2001-12-13 |
Family
ID=4560183
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2001/006430 WO2001094339A1 (en) | 2000-06-09 | 2001-06-07 | Substituted pyridine herbicides |
Country Status (27)
Country | Link |
---|---|
US (3) | US6838564B2 (en) |
EP (2) | EP1574510B1 (en) |
JP (1) | JP4965050B2 (en) |
CN (3) | CN1824662B (en) |
AR (1) | AR031243A1 (en) |
AT (1) | ATE330953T1 (en) |
AU (2) | AU6234401A (en) |
BR (1) | BR0111981B1 (en) |
CA (1) | CA2410345C (en) |
CZ (1) | CZ303727B6 (en) |
DE (1) | DE60120964T2 (en) |
DK (1) | DK1286985T3 (en) |
ES (1) | ES2266199T3 (en) |
GT (1) | GT200100103A (en) |
HK (2) | HK1054376B (en) |
HR (2) | HRP20020969B1 (en) |
HU (1) | HU228428B1 (en) |
IN (1) | IN2002CH02005A (en) |
MX (1) | MX244506B (en) |
PL (1) | PL216038B1 (en) |
PT (1) | PT1286985E (en) |
RO (3) | RO122911B1 (en) |
RU (1) | RU2326866C2 (en) |
SK (1) | SK287483B6 (en) |
UA (1) | UA74191C2 (en) |
WO (1) | WO2001094339A1 (en) |
ZA (1) | ZA200209878B (en) |
Cited By (60)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003013247A1 (en) * | 2001-08-09 | 2003-02-20 | Syngenta Participations Ag | Pyridylpropynyloxyphenyl derivatives for use as herbicides |
WO2003047342A1 (en) * | 2001-12-03 | 2003-06-12 | Syngenta Participations Ag | Herbicidal composition |
WO2003047343A1 (en) * | 2001-12-03 | 2003-06-12 | Syngenta Participations Ag | Herbicidal composition |
WO2003047344A1 (en) * | 2001-12-03 | 2003-06-12 | Syngenta Participations Ag | Herbicidal composition |
EP1352890A1 (en) | 2002-04-09 | 2003-10-15 | Syngenta Participations AG | Process for the preparation of bicyclic diketone salts |
WO2003092380A1 (en) * | 2002-04-29 | 2003-11-13 | Bayer Cropscience Aktiengesellschaft | 2,6 substituted pyridine-3-carbonyl derivatives serving as plant protection agents having herbicidal action |
WO2003106448A2 (en) * | 2002-06-14 | 2003-12-24 | Syngenta Participations Ag | Novel herbicides |
EP1388285A2 (en) * | 2002-08-07 | 2004-02-11 | Syngenta Participations AG | Herbicidal composition |
WO2004033431A2 (en) * | 2002-10-04 | 2004-04-22 | Arena Pharmaceuticals, Inc. | Hydroxypyrazoles for use against metabolic-related disorders |
WO2004058712A2 (en) * | 2002-12-30 | 2004-07-15 | Syngenta Participations Ag | Herbicidally active nicotinoyl derivates |
WO2004078729A1 (en) * | 2003-03-07 | 2004-09-16 | Syngenta Participations Ag | Process for the production of substituted nicotinic acid esters |
US6855831B2 (en) | 2002-04-09 | 2005-02-15 | Syngenta Crop Protection, Inc. | Process for the preparation of cyclic diketones |
WO2005013696A1 (en) * | 2003-07-29 | 2005-02-17 | Syngenta Participation Ag | Method of controlling weeds in transgenic crops |
WO2005058831A1 (en) * | 2003-12-12 | 2005-06-30 | Syngenta Participations Ag | Novel herbicides |
WO2005085205A1 (en) * | 2004-03-05 | 2005-09-15 | Nissan Chemical Industries, Ltd. | Substituted pyrazole compound and herbicide |
WO2005105745A1 (en) | 2004-04-30 | 2005-11-10 | Syngenta Participations Ag | Process for the production of cyclic diketones |
WO2006059103A2 (en) * | 2004-12-03 | 2006-06-08 | Peakdale Molecular Limited | Pyridine based compounds useful as intermediates for pharmaceutical or agricultural end-products |
WO2006066871A1 (en) * | 2004-12-22 | 2006-06-29 | Syngenta Participations Ag | Pyridine ketones with herbicidal effect |
EP1982978A1 (en) * | 2006-02-02 | 2008-10-22 | Kumiai Chemical Industry Co., Ltd. | Pyridone derivative and herbicide |
WO2009011321A1 (en) | 2007-07-13 | 2009-01-22 | Ishihara Sangyo Kaisha, Ltd. | Herbicidal composition |
EP2092825A1 (en) | 2008-02-21 | 2009-08-26 | Bayer CropScience Aktiengesellschaft | Herbicidal combinations comprising a herbicide of the class of the diamino-s-triazines |
WO2010001084A2 (en) | 2008-06-09 | 2010-01-07 | Syngenta Participations Ag | Herbicide composition |
EP2147600A1 (en) | 2008-07-21 | 2010-01-27 | Bayer CropScience AG | Method for weed control in lawn |
US20100216638A1 (en) * | 2007-05-29 | 2010-08-26 | Syngenta Crop Protection, Inc. | Herbicidally active bicyclic 1,3-dione compounds |
EP2241185A1 (en) | 2005-12-23 | 2010-10-20 | Basf Se | A method for controlling aquatic weeds |
EP2255637A1 (en) | 2009-05-02 | 2010-12-01 | Bayer CropScience AG | Method for weed control in lawn or turf |
EP2258177A2 (en) | 2006-12-15 | 2010-12-08 | Rohm and Haas Company | Mixtures comprising 1-methylcyclopropene |
WO2011095461A1 (en) | 2010-02-04 | 2011-08-11 | Syngenta Participations Ag | Pyridazine derivatives, processes for their preparation and their use as fungicides |
WO2011104183A1 (en) | 2010-02-24 | 2011-09-01 | Syngenta Participations Ag | Novel microbicides |
WO2012001040A1 (en) | 2010-07-02 | 2012-01-05 | Syngenta Participations Ag | Novel microbiocidal dioxime ether derivatives |
WO2012013754A1 (en) | 2010-07-29 | 2012-02-02 | Syngenta Participations Ag | Novel microbiocidal dioxime ether derivatives |
WO2012041874A1 (en) | 2010-10-01 | 2012-04-05 | Syngenta Participations Ag | Fungicidal compositions |
WO2012066122A1 (en) | 2010-11-18 | 2012-05-24 | Syngenta Participations Ag | 2 - (pyridin- 2 -yl) -quinazoline derivatives and their use as microbicides |
WO2012069652A2 (en) | 2010-11-26 | 2012-05-31 | Syngenta Participations Ag | Fungicide mixtures |
WO2012110517A1 (en) | 2011-02-15 | 2012-08-23 | Bayer Cropscience Ag | Synergistic combinations containing a dithiino-tetracarboxamide fungicide and a herbicide, safener or plant growth regulator |
WO2012116939A1 (en) | 2011-02-28 | 2012-09-07 | Basf Se | Composition comprising a pesticide, a surfactant and an alkoxylate of 2-propylheptylamine |
DE102011080004A1 (en) | 2011-07-28 | 2012-09-13 | Bayer Cropscience Ag | Use of seed treatment agents, comprising carbamate fungicides as safeners, for preventing or reducing phytotoxic effects of herbicides on useful plants, preferably cultivated plants |
DE102011080007A1 (en) | 2011-07-28 | 2012-09-13 | Bayer Cropscience Ag | Use of seed treatment agents comprising conazole or triazole fungicides e.g. as safeners for avoiding or reducing phytotoxic effects of herbicides e.g. carbamate, thiocarbamate and haloacetanilide, on crops, preferably cultural crops |
DE102011080020A1 (en) | 2011-07-28 | 2012-09-13 | Bayer Cropscience Ag | Use of seed treatment agents, comprising dicarboximide fungicides as safeners, for preventing or reducing phytotoxic effects of herbicides on useful plants, preferably cultivated plants |
DE102011079991A1 (en) | 2011-07-28 | 2012-09-13 | Bayer Crop Science Ag | Use of seed treating-agent comprising nicotinoid insecticide as a safener for avoiding or reducing phytotoxic effects of herbicide on useful plants, preferably crop plants |
DE102011079997A1 (en) | 2011-07-28 | 2012-09-13 | Bayer Corpscience Ag | Use of seed treatment agents comprising pyrazole insecticides e.g. as safeners for avoiding or reducing phytotoxic effects of herbicides e.g. carbamate, thiocarbamate and haloacetanilide, on crops, preferably cultural crops |
WO2012123416A1 (en) | 2011-03-15 | 2012-09-20 | Bayer Cropscience Ag | N-(1,2,5-oxadiazol-3-yl)pyridinecarboxamides and use thereof as herbicides |
DE102011080016A1 (en) | 2011-07-28 | 2012-10-25 | Bayer Cropscience Ag | Use of seed treatment active substance comprising strobilurin fungicides, e.g. as safeners for avoiding or reducing phytotoxic effects of herbicides on useful plants, preferably crop plants, and in crop plants protective agents |
DE102011080010A1 (en) | 2011-07-28 | 2012-10-25 | Bayer Cropscience Ag | Use of seed treatment agents comprising anilide and thiazole fungicides, e.g. as safeners for avoiding or reducing phytotoxic effects of herbicides e.g. carbamate, thiocarbamate and haloacetanilide, on crops, preferably cultural crops |
DE102011080001A1 (en) | 2011-07-28 | 2012-10-25 | Bayer Cropscience Ag | Use of seed treatment active substance comprising carbamate insecticides, e.g. as safeners for avoiding or reducing phytotoxic effects of herbicides on useful plants, preferably crop plants, and in crop plants protective agents |
WO2013011010A1 (en) | 2011-07-19 | 2013-01-24 | Syngenta Participations Ag | Fungizide mixtures |
WO2013026866A2 (en) | 2011-08-23 | 2013-02-28 | Syngenta Participations Ag | Novel microbiocides |
WO2013189777A1 (en) | 2012-06-21 | 2013-12-27 | Basf Se | Adjuvant comprising a 2-propylheptylamine alkoxylate, sugar-based surfactant, and drift-control agent and/or humectant |
US8674106B2 (en) | 2004-06-17 | 2014-03-18 | Addex Pharma Sa | Alkynyl derivatives as modulators of metabotropic glutamate receptors |
WO2014060502A1 (en) | 2012-10-19 | 2014-04-24 | Bayer Cropscience Ag | Active compound combinations comprising carboxamide derivatives |
US8969247B2 (en) | 2005-12-23 | 2015-03-03 | Basf Se | Method for controlling aquatic weeds |
US9040538B2 (en) | 2009-05-21 | 2015-05-26 | Universite Laval | Pyrimidines as novel therapeutic agents |
US9119400B2 (en) | 2010-02-04 | 2015-09-01 | Sumitomo Chemical Company, Limited | Method of controlling weeds |
WO2016001119A1 (en) | 2014-07-01 | 2016-01-07 | Bayer Cropscience Aktiengesellschaft | Insecticide and fungicide active ingredient combinations |
US9265252B2 (en) | 2011-08-10 | 2016-02-23 | Bayer Intellectual Property Gmbh | Active compound combinations comprising specific tetramic acid derivatives |
US9314022B2 (en) | 2007-04-25 | 2016-04-19 | Syngenta Crop Protection, Llc | Fungicidal compositions |
WO2019007888A1 (en) | 2017-07-06 | 2019-01-10 | Bayer Aktiengesellschaft | Insecticidal active ingredient combinations |
WO2019007887A1 (en) | 2017-07-06 | 2019-01-10 | Bayer Aktiengesellschaft | Insecticide and fungicide active ingredient combinations |
CN114716320A (en) * | 2022-06-08 | 2022-07-08 | 山东潍坊润丰化工股份有限公司 | Compound, preparation method thereof and application of compound in preparation of fluroxypyr intermediate |
WO2024132649A1 (en) | 2022-12-20 | 2024-06-27 | Syngenta Crop Protection Ag | Herbicidal compositions |
Families Citing this family (44)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GT200100103A (en) * | 2000-06-09 | 2002-02-21 | NEW HERBICIDES | |
BRPI0510492B1 (en) * | 2004-04-30 | 2015-07-21 | Syngenta Participations Ag | Process for the production of cyclic diketones, as well as their intermediates |
BR112012030008B1 (en) | 2010-05-27 | 2019-07-02 | Syngenta Participations Ag | PLANT PHYTOTOXICITY AND / OR INJURY ASSESSMENT SYSTEM, PESTICIDE-TREATED PLANT SELECTION METHOD AND PESTICIDES SELECTION METHOD |
EP2545774A1 (en) | 2011-07-12 | 2013-01-16 | Cheminova A/S | Aqueous HPPD inhibitor suspension concentrate compositions comprising smectite clay |
US11653588B2 (en) | 2018-10-26 | 2023-05-23 | Deere & Company | Yield map generation and control system |
US11957072B2 (en) | 2020-02-06 | 2024-04-16 | Deere & Company | Pre-emergence weed detection and mitigation system |
US11079725B2 (en) | 2019-04-10 | 2021-08-03 | Deere & Company | Machine control using real-time model |
US11589509B2 (en) | 2018-10-26 | 2023-02-28 | Deere & Company | Predictive machine characteristic map generation and control system |
US11641800B2 (en) | 2020-02-06 | 2023-05-09 | Deere & Company | Agricultural harvesting machine with pre-emergence weed detection and mitigation system |
US11178818B2 (en) | 2018-10-26 | 2021-11-23 | Deere & Company | Harvesting machine control system with fill level processing based on yield data |
US11467605B2 (en) | 2019-04-10 | 2022-10-11 | Deere & Company | Zonal machine control |
US12069978B2 (en) | 2018-10-26 | 2024-08-27 | Deere & Company | Predictive environmental characteristic map generation and control system |
US11672203B2 (en) | 2018-10-26 | 2023-06-13 | Deere & Company | Predictive map generation and control |
US11240961B2 (en) | 2018-10-26 | 2022-02-08 | Deere & Company | Controlling a harvesting machine based on a geo-spatial representation indicating where the harvesting machine is likely to reach capacity |
US11778945B2 (en) | 2019-04-10 | 2023-10-10 | Deere & Company | Machine control using real-time model |
US11234366B2 (en) | 2019-04-10 | 2022-02-01 | Deere & Company | Image selection for machine control |
BR112022006856A2 (en) * | 2019-10-08 | 2022-07-05 | Shenyang Sinochem Agrochemicals R & D Co Ltd | CARBOXYLATE COMPOUND CONTAINING ALKENE AND ITS USE |
US12035648B2 (en) | 2020-02-06 | 2024-07-16 | Deere & Company | Predictive weed map generation and control system |
US11477940B2 (en) | 2020-03-26 | 2022-10-25 | Deere & Company | Mobile work machine control based on zone parameter modification |
US11845449B2 (en) | 2020-10-09 | 2023-12-19 | Deere & Company | Map generation and control system |
US12069986B2 (en) | 2020-10-09 | 2024-08-27 | Deere & Company | Map generation and control system |
US11895948B2 (en) | 2020-10-09 | 2024-02-13 | Deere & Company | Predictive map generation and control based on soil properties |
US12013245B2 (en) | 2020-10-09 | 2024-06-18 | Deere & Company | Predictive map generation and control system |
US11849672B2 (en) | 2020-10-09 | 2023-12-26 | Deere & Company | Machine control using a predictive map |
US11983009B2 (en) | 2020-10-09 | 2024-05-14 | Deere & Company | Map generation and control system |
US11592822B2 (en) | 2020-10-09 | 2023-02-28 | Deere & Company | Machine control using a predictive map |
US11727680B2 (en) | 2020-10-09 | 2023-08-15 | Deere & Company | Predictive map generation based on seeding characteristics and control |
US11675354B2 (en) | 2020-10-09 | 2023-06-13 | Deere & Company | Machine control using a predictive map |
US11825768B2 (en) | 2020-10-09 | 2023-11-28 | Deere & Company | Machine control using a predictive map |
US11844311B2 (en) | 2020-10-09 | 2023-12-19 | Deere & Company | Machine control using a predictive map |
US11474523B2 (en) | 2020-10-09 | 2022-10-18 | Deere & Company | Machine control using a predictive speed map |
US11650587B2 (en) | 2020-10-09 | 2023-05-16 | Deere & Company | Predictive power map generation and control system |
US11849671B2 (en) | 2020-10-09 | 2023-12-26 | Deere & Company | Crop state map generation and control system |
US11711995B2 (en) | 2020-10-09 | 2023-08-01 | Deere & Company | Machine control using a predictive map |
US11946747B2 (en) | 2020-10-09 | 2024-04-02 | Deere & Company | Crop constituent map generation and control system |
US11871697B2 (en) | 2020-10-09 | 2024-01-16 | Deere & Company | Crop moisture map generation and control system |
US11889788B2 (en) | 2020-10-09 | 2024-02-06 | Deere & Company | Predictive biomass map generation and control |
US11874669B2 (en) | 2020-10-09 | 2024-01-16 | Deere & Company | Map generation and control system |
US11927459B2 (en) | 2020-10-09 | 2024-03-12 | Deere & Company | Machine control using a predictive map |
US11864483B2 (en) | 2020-10-09 | 2024-01-09 | Deere & Company | Predictive map generation and control system |
US11635765B2 (en) | 2020-10-09 | 2023-04-25 | Deere & Company | Crop state map generation and control system |
US11889787B2 (en) | 2020-10-09 | 2024-02-06 | Deere & Company | Predictive speed map generation and control system |
US12082531B2 (en) | 2022-01-26 | 2024-09-10 | Deere & Company | Systems and methods for predicting material dynamics |
US12058951B2 (en) | 2022-04-08 | 2024-08-13 | Deere & Company | Predictive nutrient map and control |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5260262A (en) * | 1991-12-06 | 1993-11-09 | Monsanto Company | Substituted pyridine compounds having herbicidal activity |
WO2000015615A1 (en) * | 1998-09-15 | 2000-03-23 | Syngenta Participations Ag | Pyridine ketones useful as herbicides |
WO2000039094A1 (en) * | 1998-12-23 | 2000-07-06 | Syngenta Participations Ag | Substituted pyridine herbicides |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL85347A0 (en) | 1987-02-11 | 1988-07-31 | May & Baker Ltd | Cyclic diones |
IT1219633B (en) | 1987-06-05 | 1990-05-24 | Sandoz Ag | BENZOIL-2H-PIRAN-3,5-4H, 6H-DIODES REPLACED, THEIR PREPARATION AND THEIR USE AS HERBICIDES |
EP0316491A1 (en) | 1987-11-19 | 1989-05-24 | Stauffer Agricultural Chemicals Company, Inc. | Herbicidal 2-pyridyl and 2-pyrimidine carbonyl 1,3-cyclohexanediones |
HUT50312A (en) | 1988-02-01 | 1990-01-29 | Sandoz Ag | Herbicide composition containing new dion-compounds and process for producing these compounds |
US5089046A (en) | 1988-04-04 | 1992-02-18 | Sandoz Ltd. | Aryl and heteroaryl diones |
HU206242B (en) | 1988-04-18 | 1992-10-28 | Sandoz Ag | Herbicidal compositions comprising substituted benzoyl bicyclodione derivatives as active ingredient |
IL91083A (en) | 1988-07-25 | 1993-04-04 | Ciba Geigy | Cyclohexanedione derivatives, their preparation and their use as herbicides |
JPH0259566A (en) | 1988-08-26 | 1990-02-28 | Nippon Soda Co Ltd | Production of 4-hydroxy-2h-pyran-2-one |
IT1230768B (en) | 1989-02-21 | 1991-10-29 | Agrimont Spa | DERIVATIVES OF 3,4 DEIDRO PIPERIDIN 5 ONE FOR HERBICIDE ACTIVITIES. |
JPH05503106A (en) | 1990-10-25 | 1993-05-27 | サンド・リミテッド | Heterocyclic dione derivatives as insecticides and plant growth regulators |
US5235060A (en) | 1991-07-11 | 1993-08-10 | E. I. Du Pont De Nemours And Company | Certain three component ionic substituted pyridine compounds as intermediates for preparation as herbicides |
US6063732A (en) | 1996-03-15 | 2000-05-16 | Novartis Crop Protection, Inc. | Herbicidal synergistic composition and method of weed control |
US6297198B1 (en) * | 1996-05-14 | 2001-10-02 | Syngenta Participations Ag | Isoxazole derivatives and their use as herbicides |
EP0922032A1 (en) | 1996-06-06 | 1999-06-16 | E.I. Du Pont De Nemours And Company | Herbicidal pyridinyl and pyrazolylphenyl ketones |
BR9714497A (en) | 1996-12-27 | 2000-03-21 | Nippon Soda Co | Derivatives of substituted piperidinedione, and, herbicides. |
WO1998041089A1 (en) | 1997-03-14 | 1998-09-24 | Novartis Ag | Novel herbicides |
JP3929545B2 (en) | 1997-03-25 | 2007-06-13 | 株式会社エス・ディー・エス バイオテック | Method for producing 3-acetyl-cyclopentanecarboxylic acid ester |
CA2349244A1 (en) | 1998-11-05 | 2000-05-18 | Basf Aktiengesellschaft | Method for producing 1-substituted 5-hydroxypyrazoles |
AR027928A1 (en) * | 2000-01-25 | 2003-04-16 | Syngenta Participations Ag | HERBICIDE COMPOSITION |
GT200100103A (en) | 2000-06-09 | 2002-02-21 | NEW HERBICIDES |
-
2001
- 2001-06-04 GT GT200100103A patent/GT200100103A/en unknown
- 2001-06-07 AU AU6234401A patent/AU6234401A/en active Pending
- 2001-06-07 ES ES01936439T patent/ES2266199T3/en not_active Expired - Lifetime
- 2001-06-07 AR ARP010102734A patent/AR031243A1/en active IP Right Grant
- 2001-06-07 AT AT01936439T patent/ATE330953T1/en active
- 2001-06-07 RO ROA200600864A patent/RO122911B1/en unknown
- 2001-06-07 RU RU2002135642/04A patent/RU2326866C2/en active IP Right Revival
- 2001-06-07 CZ CZ20023979A patent/CZ303727B6/en not_active IP Right Cessation
- 2001-06-07 SK SK1723-2002A patent/SK287483B6/en not_active IP Right Cessation
- 2001-06-07 MX MXPA02011977 patent/MX244506B/en active IP Right Grant
- 2001-06-07 DE DE60120964T patent/DE60120964T2/en not_active Expired - Lifetime
- 2001-06-07 AU AU2001262344A patent/AU2001262344B2/en not_active Expired
- 2001-06-07 BR BRPI0111981-8A patent/BR0111981B1/en not_active IP Right Cessation
- 2001-06-07 PT PT01936439T patent/PT1286985E/en unknown
- 2001-06-07 EP EP05011024A patent/EP1574510B1/en not_active Expired - Lifetime
- 2001-06-07 CN CN200510119289XA patent/CN1824662B/en not_active Expired - Lifetime
- 2001-06-07 HU HU0301243A patent/HU228428B1/en unknown
- 2001-06-07 EP EP01936439A patent/EP1286985B1/en not_active Expired - Lifetime
- 2001-06-07 DK DK01936439T patent/DK1286985T3/en active
- 2001-06-07 WO PCT/EP2001/006430 patent/WO2001094339A1/en active Application Filing
- 2001-06-07 PL PL358807A patent/PL216038B1/en unknown
- 2001-06-07 US US10/297,685 patent/US6838564B2/en not_active Expired - Lifetime
- 2001-06-07 CN CNA2006100998916A patent/CN1951918A/en active Pending
- 2001-06-07 CA CA2410345A patent/CA2410345C/en not_active Expired - Lifetime
- 2001-06-07 CN CNB018108903A patent/CN1231476C/en not_active Expired - Lifetime
- 2001-06-07 RO ROA200201526A patent/RO122034B1/en unknown
- 2001-06-07 RO ROA200600863A patent/RO122965B9/en unknown
- 2001-06-07 JP JP2002501888A patent/JP4965050B2/en not_active Expired - Lifetime
- 2001-07-06 UA UA2003010242A patent/UA74191C2/en unknown
-
2002
- 2002-12-04 IN IN2005CH2002 patent/IN2002CH02005A/en unknown
- 2002-12-05 ZA ZA200209878A patent/ZA200209878B/en unknown
- 2002-12-06 HR HR20020969A patent/HRP20020969B1/en not_active IP Right Cessation
-
2003
- 2003-07-17 HK HK03105194.0A patent/HK1054376B/en not_active IP Right Cessation
-
2004
- 2004-07-16 US US10/893,792 patent/US7378375B1/en not_active Expired - Lifetime
-
2006
- 2006-12-22 HK HK06114148.6A patent/HK1094197A1/en not_active IP Right Cessation
-
2008
- 2008-05-23 US US12/126,238 patent/US7691785B2/en not_active Expired - Fee Related
- 2008-12-19 HR HR20080664A patent/HRP20080664A2/en not_active Application Discontinuation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5260262A (en) * | 1991-12-06 | 1993-11-09 | Monsanto Company | Substituted pyridine compounds having herbicidal activity |
WO2000015615A1 (en) * | 1998-09-15 | 2000-03-23 | Syngenta Participations Ag | Pyridine ketones useful as herbicides |
WO2000039094A1 (en) * | 1998-12-23 | 2000-07-06 | Syngenta Participations Ag | Substituted pyridine herbicides |
Cited By (97)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003013247A1 (en) * | 2001-08-09 | 2003-02-20 | Syngenta Participations Ag | Pyridylpropynyloxyphenyl derivatives for use as herbicides |
WO2003047342A1 (en) * | 2001-12-03 | 2003-06-12 | Syngenta Participations Ag | Herbicidal composition |
WO2003047343A1 (en) * | 2001-12-03 | 2003-06-12 | Syngenta Participations Ag | Herbicidal composition |
WO2003047344A1 (en) * | 2001-12-03 | 2003-06-12 | Syngenta Participations Ag | Herbicidal composition |
AU2002361967B2 (en) * | 2001-12-03 | 2006-06-08 | Syngenta Participation Ag | Herbicidal composition |
EP1352890A1 (en) | 2002-04-09 | 2003-10-15 | Syngenta Participations AG | Process for the preparation of bicyclic diketone salts |
US7135574B2 (en) | 2002-04-09 | 2006-11-14 | Syngenta Crop Protection, Inc. | Process for the preparation of cyclic diketones |
US6911547B1 (en) | 2002-04-09 | 2005-06-28 | Syngenta Crop Protection, Inc. | Process for the preparation of bicyclic diketone salts |
US6855831B2 (en) | 2002-04-09 | 2005-02-15 | Syngenta Crop Protection, Inc. | Process for the preparation of cyclic diketones |
WO2003092380A1 (en) * | 2002-04-29 | 2003-11-13 | Bayer Cropscience Aktiengesellschaft | 2,6 substituted pyridine-3-carbonyl derivatives serving as plant protection agents having herbicidal action |
US7439207B2 (en) | 2002-04-29 | 2008-10-21 | Bayer Cropscience Ag | 2,6 substituted pyridine-3-carbonyl derivatives serving as plant protection agents having herbicidal action |
JP2005526840A (en) * | 2002-04-29 | 2005-09-08 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 2,6-substituted pyridine-3-carbonyl derivatives useful as plant protection products having herbicidal action |
AU2003276976B2 (en) * | 2002-06-14 | 2009-08-27 | Syngenta Participations Ag | Nicotinoyl derivatives as herbicidal compounds |
WO2003106448A3 (en) * | 2002-06-14 | 2004-03-04 | Syngenta Participations Ag | Nicotinoyl derivatives as herbicidal compounds |
WO2003106448A2 (en) * | 2002-06-14 | 2003-12-24 | Syngenta Participations Ag | Novel herbicides |
EP1388285A3 (en) * | 2002-08-07 | 2004-03-17 | Syngenta Participations AG | Herbicidal composition |
EP1842426A3 (en) * | 2002-08-07 | 2012-07-25 | Syngenta Participations AG | Herbicidal composition |
EP1388285A2 (en) * | 2002-08-07 | 2004-02-11 | Syngenta Participations AG | Herbicidal composition |
EP1842426A2 (en) * | 2002-08-07 | 2007-10-10 | Syngeta Participations AG | Herbicidal composition |
WO2004033431A2 (en) * | 2002-10-04 | 2004-04-22 | Arena Pharmaceuticals, Inc. | Hydroxypyrazoles for use against metabolic-related disorders |
WO2004033431A3 (en) * | 2002-10-04 | 2004-07-29 | Arena Pharm Inc | Hydroxypyrazoles for use against metabolic-related disorders |
JP2006515305A (en) * | 2002-12-30 | 2006-05-25 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | New herbicide |
WO2004058712A2 (en) * | 2002-12-30 | 2004-07-15 | Syngenta Participations Ag | Herbicidally active nicotinoyl derivates |
US7776888B2 (en) | 2002-12-30 | 2010-08-17 | Syngenta Crop Protection, Inc. | Herbicides |
WO2004058712A3 (en) * | 2002-12-30 | 2004-09-16 | Syngenta Participations Ag | Herbicidally active nicotinoyl derivates |
CN100418963C (en) * | 2002-12-30 | 2008-09-17 | 辛根塔参与股份公司 | Novel herbicides |
CN100357273C (en) * | 2003-03-07 | 2007-12-26 | 辛根塔参与股份公司 | Process for the production of substituted nicotinic acid esters |
WO2004078729A1 (en) * | 2003-03-07 | 2004-09-16 | Syngenta Participations Ag | Process for the production of substituted nicotinic acid esters |
US7488824B2 (en) | 2003-03-07 | 2009-02-10 | Syngenta Crop Protection, Inc. | Process for the production of substituted nicotinic acid esters |
WO2005013696A1 (en) * | 2003-07-29 | 2005-02-17 | Syngenta Participation Ag | Method of controlling weeds in transgenic crops |
WO2005058831A1 (en) * | 2003-12-12 | 2005-06-30 | Syngenta Participations Ag | Novel herbicides |
WO2005085205A1 (en) * | 2004-03-05 | 2005-09-15 | Nissan Chemical Industries, Ltd. | Substituted pyrazole compound and herbicide |
EP1756059A1 (en) | 2004-04-30 | 2007-02-28 | Syngeta Participations AG | Process for the production of cyclic diketones |
WO2005105745A1 (en) | 2004-04-30 | 2005-11-10 | Syngenta Participations Ag | Process for the production of cyclic diketones |
US8674106B2 (en) | 2004-06-17 | 2014-03-18 | Addex Pharma Sa | Alkynyl derivatives as modulators of metabotropic glutamate receptors |
US8883826B2 (en) | 2004-06-17 | 2014-11-11 | Addex Pharma Sa | Alkynyl derivatives as modulators of metabotropic glutamate receptors |
WO2006059103A2 (en) * | 2004-12-03 | 2006-06-08 | Peakdale Molecular Limited | Pyridine based compounds useful as intermediates for pharmaceutical or agricultural end-products |
WO2006059103A3 (en) * | 2004-12-03 | 2007-02-22 | Peakdale Molecular Ltd | Pyridine based compounds useful as intermediates for pharmaceutical or agricultural end-products |
WO2006066871A1 (en) * | 2004-12-22 | 2006-06-29 | Syngenta Participations Ag | Pyridine ketones with herbicidal effect |
US7745495B2 (en) | 2004-12-22 | 2010-06-29 | Syngenta Crop Protection, Inc. | Pyridine ketones with herbicidal effect |
US8969247B2 (en) | 2005-12-23 | 2015-03-03 | Basf Se | Method for controlling aquatic weeds |
EP2241185A1 (en) | 2005-12-23 | 2010-10-20 | Basf Se | A method for controlling aquatic weeds |
EP1982978A4 (en) * | 2006-02-02 | 2010-12-15 | Kumiai Chemical Industry Co | Pyridone derivative and herbicide |
EP1982978A1 (en) * | 2006-02-02 | 2008-10-22 | Kumiai Chemical Industry Co., Ltd. | Pyridone derivative and herbicide |
EP2258177A2 (en) | 2006-12-15 | 2010-12-08 | Rohm and Haas Company | Mixtures comprising 1-methylcyclopropene |
US11647749B2 (en) | 2007-04-25 | 2023-05-16 | Syngenta Participations Ag | Fungicidal compositions |
US10143201B2 (en) | 2007-04-25 | 2018-12-04 | Syngenta Crop Protection, Llc | Fungicidal compositions |
US9642365B2 (en) | 2007-04-25 | 2017-05-09 | Syngenta Crop Protection, Llc | Fungicidal compositions |
US9314022B2 (en) | 2007-04-25 | 2016-04-19 | Syngenta Crop Protection, Llc | Fungicidal compositions |
US20100216638A1 (en) * | 2007-05-29 | 2010-08-26 | Syngenta Crop Protection, Inc. | Herbicidally active bicyclic 1,3-dione compounds |
US8828908B2 (en) | 2007-05-29 | 2014-09-09 | Syngenta Limited | Herbicidally active bicyclic 1,3-dione compounds |
US8435928B2 (en) | 2007-07-13 | 2013-05-07 | Ishihara Sangyo Kaisha, Ltd. | Herbicidal composition |
EP3023006A1 (en) | 2007-07-13 | 2016-05-25 | Ishihara Sangyo Kaisha, Ltd. | Herbicidal composition |
WO2009011321A1 (en) | 2007-07-13 | 2009-01-22 | Ishihara Sangyo Kaisha, Ltd. | Herbicidal composition |
EP2092825A1 (en) | 2008-02-21 | 2009-08-26 | Bayer CropScience Aktiengesellschaft | Herbicidal combinations comprising a herbicide of the class of the diamino-s-triazines |
EA018972B1 (en) * | 2008-06-09 | 2013-12-30 | Зингента Партисипейшнс Аг | Herbicide composition |
WO2010001084A3 (en) * | 2008-06-09 | 2010-10-28 | Syngenta Participations Ag | Herbicide composition |
US9456604B2 (en) | 2008-06-09 | 2016-10-04 | Syngenta Crop Protection, Llc | Herbicide composition |
WO2010001084A2 (en) | 2008-06-09 | 2010-01-07 | Syngenta Participations Ag | Herbicide composition |
WO2010009819A2 (en) | 2008-07-21 | 2010-01-28 | Bayer Cropscience Ag | Method for weed control in lawn |
EP2147600A1 (en) | 2008-07-21 | 2010-01-27 | Bayer CropScience AG | Method for weed control in lawn |
EP2255637A1 (en) | 2009-05-02 | 2010-12-01 | Bayer CropScience AG | Method for weed control in lawn or turf |
US9040538B2 (en) | 2009-05-21 | 2015-05-26 | Universite Laval | Pyrimidines as novel therapeutic agents |
US9315521B2 (en) | 2009-05-21 | 2016-04-19 | UNIVERSITé LAVAL | Pyrimidines as novel therapeutic agents |
WO2011095461A1 (en) | 2010-02-04 | 2011-08-11 | Syngenta Participations Ag | Pyridazine derivatives, processes for their preparation and their use as fungicides |
US9119400B2 (en) | 2010-02-04 | 2015-09-01 | Sumitomo Chemical Company, Limited | Method of controlling weeds |
WO2011104183A1 (en) | 2010-02-24 | 2011-09-01 | Syngenta Participations Ag | Novel microbicides |
WO2012001040A1 (en) | 2010-07-02 | 2012-01-05 | Syngenta Participations Ag | Novel microbiocidal dioxime ether derivatives |
WO2012013754A1 (en) | 2010-07-29 | 2012-02-02 | Syngenta Participations Ag | Novel microbiocidal dioxime ether derivatives |
WO2012041874A1 (en) | 2010-10-01 | 2012-04-05 | Syngenta Participations Ag | Fungicidal compositions |
EP3175712A1 (en) | 2010-10-01 | 2017-06-07 | Syngenta Participations Ag | Fungicidal compositions |
WO2012066122A1 (en) | 2010-11-18 | 2012-05-24 | Syngenta Participations Ag | 2 - (pyridin- 2 -yl) -quinazoline derivatives and their use as microbicides |
WO2012069652A2 (en) | 2010-11-26 | 2012-05-31 | Syngenta Participations Ag | Fungicide mixtures |
WO2012110517A1 (en) | 2011-02-15 | 2012-08-23 | Bayer Cropscience Ag | Synergistic combinations containing a dithiino-tetracarboxamide fungicide and a herbicide, safener or plant growth regulator |
WO2012116939A1 (en) | 2011-02-28 | 2012-09-07 | Basf Se | Composition comprising a pesticide, a surfactant and an alkoxylate of 2-propylheptylamine |
WO2012123416A1 (en) | 2011-03-15 | 2012-09-20 | Bayer Cropscience Ag | N-(1,2,5-oxadiazol-3-yl)pyridinecarboxamides and use thereof as herbicides |
WO2013011010A1 (en) | 2011-07-19 | 2013-01-24 | Syngenta Participations Ag | Fungizide mixtures |
DE102011080001A1 (en) | 2011-07-28 | 2012-10-25 | Bayer Cropscience Ag | Use of seed treatment active substance comprising carbamate insecticides, e.g. as safeners for avoiding or reducing phytotoxic effects of herbicides on useful plants, preferably crop plants, and in crop plants protective agents |
DE102011080004A1 (en) | 2011-07-28 | 2012-09-13 | Bayer Cropscience Ag | Use of seed treatment agents, comprising carbamate fungicides as safeners, for preventing or reducing phytotoxic effects of herbicides on useful plants, preferably cultivated plants |
DE102011080010A1 (en) | 2011-07-28 | 2012-10-25 | Bayer Cropscience Ag | Use of seed treatment agents comprising anilide and thiazole fungicides, e.g. as safeners for avoiding or reducing phytotoxic effects of herbicides e.g. carbamate, thiocarbamate and haloacetanilide, on crops, preferably cultural crops |
DE102011080016A1 (en) | 2011-07-28 | 2012-10-25 | Bayer Cropscience Ag | Use of seed treatment active substance comprising strobilurin fungicides, e.g. as safeners for avoiding or reducing phytotoxic effects of herbicides on useful plants, preferably crop plants, and in crop plants protective agents |
DE102011080007A1 (en) | 2011-07-28 | 2012-09-13 | Bayer Cropscience Ag | Use of seed treatment agents comprising conazole or triazole fungicides e.g. as safeners for avoiding or reducing phytotoxic effects of herbicides e.g. carbamate, thiocarbamate and haloacetanilide, on crops, preferably cultural crops |
DE102011079997A1 (en) | 2011-07-28 | 2012-09-13 | Bayer Corpscience Ag | Use of seed treatment agents comprising pyrazole insecticides e.g. as safeners for avoiding or reducing phytotoxic effects of herbicides e.g. carbamate, thiocarbamate and haloacetanilide, on crops, preferably cultural crops |
DE102011079991A1 (en) | 2011-07-28 | 2012-09-13 | Bayer Crop Science Ag | Use of seed treating-agent comprising nicotinoid insecticide as a safener for avoiding or reducing phytotoxic effects of herbicide on useful plants, preferably crop plants |
DE102011080020A1 (en) | 2011-07-28 | 2012-09-13 | Bayer Cropscience Ag | Use of seed treatment agents, comprising dicarboximide fungicides as safeners, for preventing or reducing phytotoxic effects of herbicides on useful plants, preferably cultivated plants |
US9265252B2 (en) | 2011-08-10 | 2016-02-23 | Bayer Intellectual Property Gmbh | Active compound combinations comprising specific tetramic acid derivatives |
WO2013026866A2 (en) | 2011-08-23 | 2013-02-28 | Syngenta Participations Ag | Novel microbiocides |
WO2013189777A1 (en) | 2012-06-21 | 2013-12-27 | Basf Se | Adjuvant comprising a 2-propylheptylamine alkoxylate, sugar-based surfactant, and drift-control agent and/or humectant |
WO2014060502A1 (en) | 2012-10-19 | 2014-04-24 | Bayer Cropscience Ag | Active compound combinations comprising carboxamide derivatives |
WO2016001119A1 (en) | 2014-07-01 | 2016-01-07 | Bayer Cropscience Aktiengesellschaft | Insecticide and fungicide active ingredient combinations |
WO2019007888A1 (en) | 2017-07-06 | 2019-01-10 | Bayer Aktiengesellschaft | Insecticidal active ingredient combinations |
WO2019007887A1 (en) | 2017-07-06 | 2019-01-10 | Bayer Aktiengesellschaft | Insecticide and fungicide active ingredient combinations |
CN114716320A (en) * | 2022-06-08 | 2022-07-08 | 山东潍坊润丰化工股份有限公司 | Compound, preparation method thereof and application of compound in preparation of fluroxypyr intermediate |
CN115232008A (en) * | 2022-06-08 | 2022-10-25 | 山东潍坊润丰化工股份有限公司 | Compound, preparation method thereof and application of compound in preparation of fluroxypyr intermediate |
WO2023237027A1 (en) * | 2022-06-08 | 2023-12-14 | 山东潍坊润丰化工股份有限公司 | Compound, method for preparing same, and use thereof in preparing bicyclopyrone intermediate |
CN115232008B (en) * | 2022-06-08 | 2024-05-17 | 山东潍坊润丰化工股份有限公司 | Compound, preparation method thereof and application of compound in preparation of fluroxypyr intermediate |
WO2024132649A1 (en) | 2022-12-20 | 2024-06-27 | Syngenta Crop Protection Ag | Herbicidal compositions |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7691785B2 (en) | Substituted pyridine herbicides | |
AU2001262344A1 (en) | Substituted pyridine herbicides | |
CA2354387C (en) | Substituted pyridine herbicides | |
CA2396587C (en) | Pyridine ketone herbicide compositions | |
EP1601653B1 (en) | Process for the production of substituted nicotinic acid esters | |
AU2002361967B2 (en) | Herbicidal composition | |
US6673938B1 (en) | Substituted pyridine herbicides | |
WO2005013696A1 (en) | Method of controlling weeds in transgenic crops | |
MXPA01006486A (en) | Substituted pyridine herbicides |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG US UZ VN YU ZA ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2001262344 Country of ref document: AU |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2001936439 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2410345 Country of ref document: CA |
|
ENP | Entry into the national phase |
Ref document number: 2002 200201526 Country of ref document: RO Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: PA/a/2002/011977 Country of ref document: MX |
|
WWE | Wipo information: entry into national phase |
Ref document number: PV2002-3979 Country of ref document: CZ Ref document number: IN/PCT/2002/2005/CHE Country of ref document: IN |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2002/09878 Country of ref document: ZA Ref document number: 200209878 Country of ref document: ZA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 17232002 Country of ref document: SK Ref document number: 10297685 Country of ref document: US Ref document number: P20020969A Country of ref document: HR |
|
ENP | Entry into the national phase |
Ref document number: 2002 501888 Country of ref document: JP Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 018108903 Country of ref document: CN |
|
ENP | Entry into the national phase |
Ref document number: 2002135642 Country of ref document: RU Kind code of ref document: A Ref country code: RU Ref document number: RU A |
|
WWP | Wipo information: published in national office |
Ref document number: 2001936439 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: PV2002-3979 Country of ref document: CZ |
|
REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |
|
WWG | Wipo information: grant in national office |
Ref document number: 2001262344 Country of ref document: AU |
|
WWG | Wipo information: grant in national office |
Ref document number: 2001936439 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref document number: PI0111981 Country of ref document: BR |
|
WWE | Wipo information: entry into national phase |
Ref document number: P20080664A Country of ref document: HR |