WO1999007698A1 - (hetero)aryloxypyrazoles utilises comme herbicides - Google Patents

(hetero)aryloxypyrazoles utilises comme herbicides Download PDF

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Publication number
WO1999007698A1
WO1999007698A1 PCT/EP1998/004730 EP9804730W WO9907698A1 WO 1999007698 A1 WO1999007698 A1 WO 1999007698A1 EP 9804730 W EP9804730 W EP 9804730W WO 9907698 A1 WO9907698 A1 WO 9907698A1
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WO
WIPO (PCT)
Prior art keywords
fluorine
chlorine
optionally substituted
cyano
methyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP1998/004730
Other languages
German (de)
English (en)
Inventor
Karl-Heinz Linker
Joachim Kluth
Markus Dollinger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Priority to AU90707/98A priority Critical patent/AU9070798A/en
Publication of WO1999007698A1 publication Critical patent/WO1999007698A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P13/00—Herbicides; Algicides
    • 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
    • C07D401/12—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 chain containing hetero atoms as chain links
    • 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
    • C07D405/12—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 chain containing hetero atoms as chain links

Definitions

  • the invention relates to new (hetero) aryloxypyrazoles, a process for their preparation and their use as herbicides.
  • A represents nitrogen or the groups C-H or C-halogen
  • Rl represents cyano or haloalkyl
  • R. represents hydrogen, cyano or halogen
  • R.3 represents hydrogen, halogen or in each case optionally substituted alkyl or alkoxy,
  • R4 stands for cyano or the grouping -CO-R ⁇ , R ⁇ represents hydrogen or optionally substituted alkyl,
  • R 6 represents the groupings -OR 7 or -N (R 8 R 9 ),
  • R 7 represents hydrogen or optionally substituted alkyl, alkenyl,
  • R 8 represents hydrogen or represents optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, and
  • R 9 has the same meaning as R 8 , but without being identical to R 8 in each individual case, or together with R 8 represents alkanediyl which may be interrupted by oxygen.
  • the invention preferably relates to compounds of the formula (I) in which
  • A represents nitrogen or the groups C-H, C-F or C-Cl
  • R * represents cyano or alkyl having 1 to 6 carbon atoms substituted by fluorine and / or chlorine,
  • R ⁇ represents hydrogen, cyano, fluorine, chlorine or bromine
  • R 3 represents hydrogen, fluorine, chlorine, bromine or alkyl or alkoxy, each optionally substituted by fluorine and / or chlorine, each having 1 to 6 carbon atoms,
  • R ⁇ stands for cyano or the grouping -CO-R ", R ⁇ represents hydrogen or alkyl having 1 to 6 carbon atoms optionally substituted by fluorine and / or chlorine,
  • R 6 represents the groupings -OR 7 or -N (R 8 R 9 ),
  • R 7 represents hydrogen, in each case optionally substituted by fluorine and / or chlorine alkyl, alkenyl or alkynyl each having up to 6 carbon atoms or by cycloalkyl optionally having fluorine, chlorine and / or methyl having 3 to 6 carbon atoms,
  • R 8 for hydrogen, for optionally substituted by fluorine, chlorine, methoxy or ethoxy alkyl with 1 to 6 carbon atoms, for each optionally substituted by fluorine and / or chlorine alkenyl or alkynyl each with 2 to 6 carbon atoms, for each optionally substituted by fluorine, chlorine and / or methyl substituted cycloalkyl or cycloalkylalkyl with 3 to 6
  • R 9 has the same meaning as R 8 , but without being identical to R 8 in each individual case, or together with R 8 represents alkanediyl having 2 to 6 carbon atoms which may be interrupted by oxygen.
  • the invention relates in particular to compounds of the formula (I) in which A represents nitrogen or the groups CH, CF or C-Cl,
  • Rl represents cyano or trifluoromethyl
  • R2 represents hydrogen, cyano, fluorine, chlorine or bromine
  • R 3 represents hydrogen, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n-, each optionally substituted by fluorine and / or chlorine. or i-propoxy,
  • R4 stands for cyano or the grouping -CO-R °
  • R5 represents hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by fluorine and / or chlorine,
  • R 6 represents the groupings -OR 7 or -N (R 8 R 9 ),
  • R 7 for hydrogen, for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl optionally substituted by fluorine and / or chlorine,
  • R 8 for hydrogen, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, for each optionally substituted by fluorine and / or chlorine Propenyl, butenyl, propynyl or butynyl, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by fluorine, chlorine and / or methyl, each optionally substituted by nitro, cyano, fluorine, chlorine, Bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, Methoxy,
  • R 9 has the same meaning as R 8 , but without being identical to R 8 in each individual case, or together with R 8 for ethane-1,2-diyl (dimethylene), propane-1,3-diyl (trimethylene), Butane-1,4-diyl, (tetramethylene), pentane-1,5-diyl (pentamethylene), hexane-1,6-diyl (hexamethylene) or 3-oxapentane-1,5-diyl.
  • hydrocarbon chains such as alkyl
  • the hydrocarbon chains are also straight-chain or branched, in each case in conjunction with heteroatoms, such as in alkoxy.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.
  • the new (hetero) aryloxypyrazoles of the general formula (I) are notable for strong and selective herbicidal activity.
  • R 3 , R ⁇ and R ⁇ have the meaning given above,
  • halogen compounds to be used as starting materials in the process according to the invention for the preparation of compounds of the formula (I) are generally defined by the formula (II).
  • R ⁇ and R ⁇ preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R * and R ⁇ ;
  • X preferably represents fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • the starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. J. Fluorine Chem. 30 (1985), 251-258; J. Heterocycl. Chem. 28 (1991), 971-976).
  • Formula (III) provides a general definition of the hydroxypyrazoles to be used as starting materials in the process according to the invention for the preparation of compounds of the formula (I).
  • R 3 , R4 and R ⁇ preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R 3 , R ⁇ and R ⁇ were specified.
  • the starting materials of the general formula (III) are known and / or can be prepared by processes known per se (cf. Chem. Ber. 109 (1976), 253-260; loc. Cit. 112 (1979), 1712-1716; loc. cit. 116 (1983), 1525-1530; DE-A-22 19 484).
  • the reaction auxiliaries for the process according to the invention for the preparation of compounds of the general formula (I) are generally the usual organic or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkanolates, such as, for example, sodium, potassium or calcium acetate, lithium, sodium, potassium or Calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, Sodium or potassium methoxide, ethanolate, n or i propanolate, n, i, s or t butanolate; also basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethyl-cyclohexylamine, dicyclohexy
  • Inert organic solvents are particularly suitable as diluents for carrying out the process according to the invention. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated
  • Hydrocarbons such as gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl s
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred at the required temperature for several hours. Working up is carried out according to customary methods (cf. the production examples).
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • the compounds are suitable for total weed control, for example on industrial and rail tracks and on paths and squares with and without tree cover.
  • the compounds for weed control in permanent crops for example forest, ornamental wood, fruit, wine , Citrus, nut, banana, coffee, tea, gum, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture fields and for selective weed control in annual crops
  • the compounds of formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both in the pre-emergence and in the post-emergence process
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, Powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as very fine encapsulations in polymeric substances.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, that is liquid solvents and / or solid
  • Carriers where appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as
  • Possible solid carriers are: e.g. Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust,
  • natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth
  • synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, se
  • coconut shells, corn cobs and tobacco stems as emulsifying and / or foaming agents are possible: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite waste liquor and
  • Methyl cellulose Methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.
  • herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (sodium), aclonifen, alachlor, alloxydim (sodium),
  • Cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Difenzoquat, Diflufenican, Dime requirementson, Dimepiperate, Dimethachlor, Di- methametryn, dimethenamid, dinitramine, diphenamide, diquat, dithiopyr, diuron,
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, spraying or scattering.
  • the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is watered with the active ingredient preparation.
  • the amount of water per unit area is expediently kept constant.
  • the active ingredient concentration in the preparation is irrelevant, the decisive factor is only the amount of active ingredient per unit area
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Test plants with a height of 5-15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area.
  • the concentration of the spray liquor is chosen so that in
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

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

Abstract

L'invention concerne des (hétéro)aryloxypyrazoles de la formule générale (I) dans laquelle les restes R1 et R5 ont les significations mentionnées dans la description. L'invention concerne en outre un procédé permettant de préparer lesdits composés et leur utilisation comme herbicides.
PCT/EP1998/004730 1997-08-11 1998-07-29 (hetero)aryloxypyrazoles utilises comme herbicides Ceased WO1999007698A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU90707/98A AU9070798A (en) 1997-08-11 1998-07-29 (hetero)aryloxypyrazoles used as herbicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19734664A DE19734664A1 (de) 1997-08-11 1997-08-11 (Hetero)Aryloxypyrazole
DE19734664.2 1997-08-11

Publications (1)

Publication Number Publication Date
WO1999007698A1 true WO1999007698A1 (fr) 1999-02-18

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PCT/EP1998/004730 Ceased WO1999007698A1 (fr) 1997-08-11 1998-07-29 (hetero)aryloxypyrazoles utilises comme herbicides

Country Status (3)

Country Link
AU (1) AU9070798A (fr)
DE (1) DE19734664A1 (fr)
WO (1) WO1999007698A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004074257A1 (fr) * 2003-02-18 2004-09-02 F. Hoffmann-La Roche Ag Inhibiteurs de transcriptase inverse non nucleoside

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8324265B2 (en) * 2005-11-21 2012-12-04 Shionogi & Co., Ltd. Heterocyclic compounds having type I 11β hydroxysteroid dehydrogenase inhibitory activity

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5071696A (fr) * 1973-11-01 1975-06-13
US4298749A (en) * 1978-07-04 1981-11-03 Basf Aktiengesellschaft Pyrazole ether derivatives
EP0295233A2 (fr) * 1987-06-08 1988-12-14 Monsanto Company 3-(4-Nitrophénoxy)pyrazoles et leur utilisation comme herbicides
WO1993004044A1 (fr) * 1991-08-20 1993-03-04 Korea Research Institute Of Chemical Technology Derives d'uree de benzoyle contenant du pyrazole, composition et utilisation
WO1997018196A1 (fr) * 1995-11-15 1997-05-22 Zeneca Limited Composes herbicides a base de pyrazole substitue

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5071696A (fr) * 1973-11-01 1975-06-13
US4298749A (en) * 1978-07-04 1981-11-03 Basf Aktiengesellschaft Pyrazole ether derivatives
EP0295233A2 (fr) * 1987-06-08 1988-12-14 Monsanto Company 3-(4-Nitrophénoxy)pyrazoles et leur utilisation comme herbicides
WO1993004044A1 (fr) * 1991-08-20 1993-03-04 Korea Research Institute Of Chemical Technology Derives d'uree de benzoyle contenant du pyrazole, composition et utilisation
WO1997018196A1 (fr) * 1995-11-15 1997-05-22 Zeneca Limited Composes herbicides a base de pyrazole substitue

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 83, no. 13, 29 September 1975, Columbus, Ohio, US; abstract no. 114400z, page 559; XP002084574 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004074257A1 (fr) * 2003-02-18 2004-09-02 F. Hoffmann-La Roche Ag Inhibiteurs de transcriptase inverse non nucleoside
RU2305680C2 (ru) * 2003-02-18 2007-09-10 Ф.Хоффманн-Ля Рош Аг Ненуклеозидные ингибиторы обратной транскриптазы, их применение, фармацевтическая композиция для ингибирования вич

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DE19734664A1 (de) 1999-02-18
AU9070798A (en) 1999-03-01

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