WO1996020146A1 - Werwendung von pyrazolderivaten mit hydrophoben resten als nitrifikationsinhibitoren - Google Patents
Werwendung von pyrazolderivaten mit hydrophoben resten als nitrifikationsinhibitoren Download PDFInfo
- Publication number
- WO1996020146A1 WO1996020146A1 PCT/EP1995/004953 EP9504953W WO9620146A1 WO 1996020146 A1 WO1996020146 A1 WO 1996020146A1 EP 9504953 W EP9504953 W EP 9504953W WO 9620146 A1 WO9620146 A1 WO 9620146A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- halogen
- radicals
- alkyl
- pyrazole derivatives
- pyrazole
- Prior art date
Links
- 0 Cc1c(C)[n](C)nc1* Chemical compound Cc1c(C)[n](C)nc1* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
- C08J3/243—Two or more independent types of crosslinking for one or more polymers
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
- C05G3/00—Mixtures of one or more fertilisers with additives not having a specially fertilising activity
- C05G3/90—Mixtures of one or more fertilisers with additives not having a specially fertilising activity for affecting the nitrification of ammonium compounds or urea in the soil
-
- 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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D231/16—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2321/00—Characterised by the use of unspecified rubbers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P60/00—Technologies relating to agriculture, livestock or agroalimentary industries
- Y02P60/20—Reduction of greenhouse gas [GHG] emissions in agriculture, e.g. CO2
- Y02P60/21—Dinitrogen oxide [N2O], e.g. using aquaponics, hydroponics or efficiency measures
Definitions
- the present invention relates to the use of pyrazole derivatives of the formula I.
- R 1 , R 2 and R 3 C ⁇ ⁇ to C 2 o-alkyl, C 3 - to C ⁇ -cycloalkyl, C 5 - to C 20 -Ar l or C ⁇ - to C 2 o-alkylaryl, these 4 radicals can be substituted once or twice by halogen and / or hydroxyl, as well as halogen, nitro or hydrogen and
- the invention further relates to new pyrazole derivatives which are suitable for this use and to processes for their preparation.
- nitrification inhibitors In order to provide plants with the nitrogen they need, they are known to be fertilized with ammonium compounds. However, ammonium compounds are microbially converted to nitrate in the soil in a relatively short time (nitrification). However, because nitrate is washed out of the soil more easily than ammonium and the washed-out portion is no longer available for plant nutrition, rapid nitrification is undesirable. In order to make better use of the fertilizer, it has therefore been proposed to add nitrification inhibitors to the soil.
- pyrazole derivatives as nitrification inhibitors is also described in US Pat. No. 4,969,946.
- the nitrogen atoms in the pyrazole ring are unsubstituted and several of the ring carbon atoms are substituted by halogen or methyl.
- DE-A 3 704 359 relates to agents which inhibit nitrification. They contain as active ingredient pyrazole derivatives which have a radical of the formula on a nitrogen atom of the pyrazole ring
- R f is a substituted or unsubstituted organic radical or a hydroxyl radical.
- nitrification inhibitors are known from EP-A 0 160 804. These are pyrazole derivatives in which a nitrogen atom in the pyrazole ring carries a substituted oxicarbonyl, sulfinyl or sulfonyl radical.
- DE-A 4 018 395 lists derivatives of l-cyanyl-3-methylpyrazole and its acid addition products or coordination compounds as nitrification inhibitors.
- SU-A 1 470 737 discloses N-hydroxymethyl derivatives of pyrazole.
- the object of the present invention was therefore to provide substances which act as nitrification inhibitors and which do not have the disadvantages mentioned.
- pyrazole derivatives of the formula I particularly preferably contain units of 4-halopyrazoles such as 4-bromo-pyrazole and 4-chloropyrazole, methylpyrazoles such as 4-methylpyrazole and 3-methylpyrazole and 4-halo-3-methylpyrazoles such as
- Ci to C 2 o-alkyl radicals where 1 to 4, preferably 1 or 2, hydrogen atoms through a radical of the formula II
- radicals R 4 with the meaning given under (a) include unsubstituted branched and above all unbranched C 6 -C 20 -alkyl radicals, in particular those with an even number of carbon atoms, such as C 6 -C 10 -, C 12 -, C 14 -, Ci 6 - # or Ci ⁇ residues are particularly preferred.
- radicals R 4 with the meaning given under (b) are in particular Ci to C ⁇ -alkyl radicals in which 2, preferably a hydrogen atom, are substituted by a radical of the formula II is considered, wherein particularly preferred compounds are those of the formula Ia.
- R 5 , R 6 and R 7 are those which are also preferred as substituents R 1 , R 2 or R 3 .
- Compounds in which R 1 and R 5 , R 2 and R 6 and R 3 and R 7 each have the same meaning are particularly easily accessible, as are those in which R 1 and R 7 , R 2 and R 6 and R in each case 3 and R 5 each have the same meaning.
- R 1 , R 2 or R 3 and one or 2 of the radicals R 5 , R 6 or R 7 are halogen, preferably CI or F, or is methyl or ethyl, for example the compound in which R 3 and R 5 are hydrogen, R 1 and R 7 are methyl and R 2 and R 6 are hydrogen or in R 3 and R 7 are hydrogen, R 1 and R 5 are methyl and R 2 and R 6 is hydrogen.
- the pyrazole derivatives of formula I can be in free form or in the form of their salts, i.e. be used as acid addition or coordination compound.
- These salts are preferably derived from mineral acids such as hydrochloric acid, sulfuric acid, phosphoric acid or nitric acid.
- the compounds are accessible by generally known methods, for example as described in EP-A 0 474 037.
- a suitable hydrazine derivative reacts with a suitable derivative of a but-2-ene (1,4) diol, but-1-ene (3,4) diol or but-1-in-3-ol the corresponding pyrazole derivatives.
- pyrazole derivatives of the formula I which have a radical R 4 with the meaning given under (a) can also be prepared in a simple manner by using a pyrazole derivative of the formula III
- radicals R x , R v and R z are the same radicals which are also suitable as radicals R 1 , R 2 , R 3 , R 5 , R 6 or R 7 , with a C 6 - to C 2 o ⁇ haloalkane (haloalkane a) which carries at least one iodine, bromine or chlorine atom and optionally one or two further halogen atoms.
- haloalkane a which carries at least one iodine, bromine or chlorine atom and optionally one or two further halogen atoms.
- a haloalkane (a) which carries one substitutable halogen atom more than the desired number in the substituent R 4 . It is generally known in the art how the reaction conditions are to be selected that the substitution of an iodine, bromine or chlorine atom in the haloalkane (a) used takes place only once. The desired result can be achieved, for example, by using the haloalkanes (a) in a high molecular excess, based on the pyrazole derivatives of the formula III.
- a radical R in a pyrazole derivative of the formula III in a pyrazole derivative of the formula I has a radical R 1 , a radical R y a radical R 2 and a radical R z corresponds to a radical R 3 .
- the pyrazole derivatives or formula I in which the radical R 4 has the meaning given under (b) are obtained in an analogous manner to those in which the radical R 4 has the meaning given under (a) from a pyrazole derivative of Formula III and a C ⁇ ⁇ to C 2 o ⁇ di- to tetrahaloalkane (haloalkane b), wherein at least 2 of the halogen atoms are iodine, chlorine or bromine.
- the pyrazole derivatives of the formula Ib can be obtained from a pyrazole derivative of the formula III and dibromo, diiodo or dichloromethane.
- both pyrazole derivatives of the formula Ib in each of which R 1 and R 5 , and R 3 and R 7 each have the same meaning as well as those in which R 1 and R 7 and R 3 and R 5 each have the same meaning.
- the number of iodine, chlorine or bromine atoms in the haloalkane (b) which are substituted by a pyrazole derivative of the formula III can be determined by the choice of the stoichiometric ratios.
- the reaction of the haloalkanes (a) or (b) with a pyrazole derivative of the formula III is advantageously carried out at from 0 to 80 ° C. under atmospheric pressure in an inert solvent, for example a polyglycol, acetonitrile or dimethyl sulfoxide, in the presence of, based on the starting product of the formula III, in approximately equimolar amounts of an organic or inorganic base, for example an alkali metal hydroxide or a tertiary amine, and catalytic amounts of a phase transfer catalyst.
- Suitable phase transfer catalysts are C 2 -C 3 o-alkylammonium hydroxides, for example octyltriethylammonium hydroxide, or polyether bonds, for example a crown ether.
- the pyrazole derivatives of the formula I are used as nitrification inhibitors by the generally customary processes.
- they can be applied directly to the floor in the form of a powder or in granulated form and in the form of an aqueous suspension.
- nitrification inhibitors with a mineral fertilizer, in particular a nitrogen fertilizer, are also advantageously used. Such mixtures preferably contain 500 to 10,000 ppm by weight of nitrification inhibitor, based on the mineral fertilizer. Mixtures of the type described in DE-A 4 128 828 have proven particularly useful. According to this preferred teaching, granules of mineral fertilizers are impregnated with a nitrification inhibitor by spraying them with a solution or suspension of the nitrification inhibitor and drying them again. The sealing of the impregnated granules with a praffin wax proposed in DE-A 4 128 828 is generally not necessary due to the substantially lower volatility of the nitrification inhibitors according to the invention. The nitrification inhibitors are usually applied to the soil in amounts of 100 g / ha to 10 kg / ha.
- the pyrazole derivatives of the formula I which can be prepared in a simple manner from inexpensive starting products are notable for their use as nitrification inhibitors above all in that they effectively inhibit the nitrification of ammonium nitrogen in the soil over a long period of time.
- these compounds are hardly toxic, have a low vapor pressure and are well sorbed in the soil. As a result, they are neither released into the atmosphere to any appreciable extent by sublimation, nor are they easily washed out by water. This results on the one hand in economic advantages such as a high level of economy due to the longer-lasting effect of the nitrification inhibitors and on the other hand in ecological advantages such as a reduction in the pollution of air and surface water and groundwater.
- the vapor pressure was measured at 20 ° C in accordance with OECD Guideline 79/831 / EEC V, updated version from February 1990, part A4.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Soil Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP95942160A EP0799168A1 (de) | 1994-12-23 | 1995-12-14 | Werwendung von pyrazolderivaten mit hydrophoben resten als nitrifikationsinhibitoren |
JP8520169A JPH10511336A (ja) | 1994-12-23 | 1995-12-14 | 疎水性基を有するピラゾール誘導体の硝化抑制剤としての使用 |
AU43450/96A AU4345096A (en) | 1994-12-23 | 1995-12-14 | Use of pyrazole derivatives with hydrophobic groups as nitrification inhibitors |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP4446194.1 | 1994-12-23 | ||
DE4446194A DE4446194A1 (de) | 1994-12-23 | 1994-12-23 | Verwendung von Pyrazolderivaten mit hydrophoben Resten als Nitrifikationsinhibitoren |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1996020146A1 true WO1996020146A1 (de) | 1996-07-04 |
Family
ID=6536849
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1995/004953 WO1996020146A1 (de) | 1994-12-23 | 1995-12-14 | Werwendung von pyrazolderivaten mit hydrophoben resten als nitrifikationsinhibitoren |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0799168A1 (de) |
JP (1) | JPH10511336A (de) |
AU (1) | AU4345096A (de) |
CA (1) | CA2208529A1 (de) |
DE (1) | DE4446194A1 (de) |
WO (1) | WO1996020146A1 (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3124473A1 (de) | 2015-07-31 | 2017-02-01 | Ludwig-Maximilians-Universität München | Bis (3,4,5-trinitropyrazolyl)methan und bis (3,5-dinitro-4-aminopyrazolyl)methan als explosivestoffe |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19631764A1 (de) | 1996-08-06 | 1998-02-12 | Basf Ag | Neue Nitrifikationsinhibitoren sowie die Verwendung von Polysäuren zur Behandlung von Mineraldüngemitteln die einen Nitrifikationsinhibitor enthalten |
DE19645313A1 (de) | 1996-11-04 | 1998-05-07 | Basf Ag | Substituierte 3-Benzylpyrazole |
DE10343277A1 (de) | 2003-09-18 | 2005-04-21 | Piesteritz Stickstoff | N-(1H-Azolyl-methyl)amide, Verfahren zu ihrer Herstellung und ihre Verwendung als Nitrifikationsinhibitoren |
DE102006015705B4 (de) | 2006-04-04 | 2018-07-19 | Skw Stickstoffwerke Piesteritz Gmbh | 1,2-Bis-(azol-1-yl)-ethan-1,2-diol-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Nitrifikationsinhibitoren |
DE102008020785B4 (de) | 2008-04-25 | 2021-11-04 | Skw Stickstoffwerke Piesteritz Gmbh | Verwendung von einfachen Derivaten von 5-Amino-1,2,4-thiadiazol zur Hemmung bzw. Steuerung der Nitrifikation |
DE102011120098B4 (de) | 2011-12-02 | 2021-02-11 | Skw Stickstoffwerke Piesteritz Gmbh | N-(1H-Pyrazolyl-methyl)formamide, Verfahren zu ihrer Herstellung und ihre Verwendung als Nitrifikationsinhibitoren |
BR112020016426A2 (pt) * | 2018-02-28 | 2020-12-15 | Basf Se | Uso de um composto alcoxi pirazol n-funcionalizado, composição para uso na redução de nitrificação, mistura agroquímica, método para reduzir a nitrificação e método para tratar um fertilizante |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1592516A (en) * | 1977-11-02 | 1981-07-08 | Fahlberg List Magdeberg Chemis | Method for inhibiting or regulating the nitrification of ammonium nitrogen in cultivated soils |
US4522642A (en) * | 1984-06-25 | 1985-06-11 | The Dow Chemical Company | Soil treating method and composition for conserving nitrogen in soil |
EP0278445A1 (de) * | 1987-02-12 | 1988-08-17 | BASF Aktiengesellschaft | Azolhalbaminal-Derivate und ihre Verwendung als Nitrifikationsinhibitoren |
US4969946A (en) * | 1986-01-29 | 1990-11-13 | The Dow Chemical Company | Soil treating method and composition for conserving nitrogen in naturally alkaline soil |
-
1994
- 1994-12-23 DE DE4446194A patent/DE4446194A1/de not_active Withdrawn
-
1995
- 1995-12-14 AU AU43450/96A patent/AU4345096A/en not_active Abandoned
- 1995-12-14 CA CA002208529A patent/CA2208529A1/en not_active Abandoned
- 1995-12-14 WO PCT/EP1995/004953 patent/WO1996020146A1/de not_active Application Discontinuation
- 1995-12-14 EP EP95942160A patent/EP0799168A1/de not_active Withdrawn
- 1995-12-14 JP JP8520169A patent/JPH10511336A/ja active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1592516A (en) * | 1977-11-02 | 1981-07-08 | Fahlberg List Magdeberg Chemis | Method for inhibiting or regulating the nitrification of ammonium nitrogen in cultivated soils |
US4522642A (en) * | 1984-06-25 | 1985-06-11 | The Dow Chemical Company | Soil treating method and composition for conserving nitrogen in soil |
US4969946A (en) * | 1986-01-29 | 1990-11-13 | The Dow Chemical Company | Soil treating method and composition for conserving nitrogen in naturally alkaline soil |
EP0278445A1 (de) * | 1987-02-12 | 1988-08-17 | BASF Aktiengesellschaft | Azolhalbaminal-Derivate und ihre Verwendung als Nitrifikationsinhibitoren |
Non-Patent Citations (4)
Title |
---|
BULL. SOC. CHIM. FR, FR * |
CHEMICAL ABSTRACTS, vol. 78, no. 3, 22 January 1973, Columbus, Ohio, US; abstract no. 16094, DZIOMKO ET AL: "Bis(3, 4, 5-trialkyl-1-pyrazolyl)methanes" page 387; * |
CHEMICAL ABSTRACTS, vol. 99, no. 1, 4 July 1983, Columbus, Ohio, US; abstract no. 5562, CLARAMUNT, ROSA MARIA ET AL: "(N-polyazolyl)methanes. II. Synthesis and reactivity of 1,1'-methylenedipyrazoles" page 509; * |
METODY POLUCH. KHIM. REAKTIV. PREP., no. 23, USSR, pages 58 - 60 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3124473A1 (de) | 2015-07-31 | 2017-02-01 | Ludwig-Maximilians-Universität München | Bis (3,4,5-trinitropyrazolyl)methan und bis (3,5-dinitro-4-aminopyrazolyl)methan als explosivestoffe |
WO2017021029A1 (en) | 2015-07-31 | 2017-02-09 | Ludwig-Maximilians-Universität München | Bis(3,4,5-trinitropyrazolyl)methane and bis(3,5-dinitro-4-aminopyrazolyl)methane as explosives |
Also Published As
Publication number | Publication date |
---|---|
CA2208529A1 (en) | 1996-07-04 |
JPH10511336A (ja) | 1998-11-04 |
EP0799168A1 (de) | 1997-10-08 |
AU4345096A (en) | 1996-07-19 |
DE4446194A1 (de) | 1996-06-27 |
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