AU2001246537A1 - 1h-pyrazole derivatives, method for the production thereof and their use for inhibiting and controlling nitrification - Google Patents
1h-pyrazole derivatives, method for the production thereof and their use for inhibiting and controlling nitrificationInfo
- Publication number
- AU2001246537A1 AU2001246537A1 AU2001246537A AU4653701A AU2001246537A1 AU 2001246537 A1 AU2001246537 A1 AU 2001246537A1 AU 2001246537 A AU2001246537 A AU 2001246537A AU 4653701 A AU4653701 A AU 4653701A AU 2001246537 A1 AU2001246537 A1 AU 2001246537A1
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- aryl
- cycloalkyl
- radical
- alkylaryl
- 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.)
- Abandoned
Links
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 title abstract 2
- 230000002401 inhibitory effect Effects 0.000 title abstract 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 abstract 8
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 4
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- -1 cyano, carbonyl Chemical group 0.000 abstract 1
- 230000002209 hydrophobic effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003217 pyrazoles Chemical class 0.000 abstract 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Fertilizers (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention concerns the use of hydrophobic, thermostable and not easily volatile 1H pyrazole derivatives of general formula (I) and to their acid addition products as agents for inhibiting or controlling nitrification, wherein R<1> and R<3> independently represent H or a C1-C4-alkyl radical; R<2> represents H, halogen or a C1-C4-alkyl radical or R<1> and R<2> together represent a five or six-membered cycloalkyl radical; R<4> represents C1-C20-alkyl, C3-C8-cycloalkyl, C6-C10-aryl or alkylaryl with C1-C4-alkyl and C6-C10-aryl groups and R<5> represents H, C1-C20-alkyl, C3-C8-cycloalkyl, C6-C10-aryl or alkylaryl with C1-C4-alkyl and C6-C10-aryl groups, whereby radicals R<4> and R<5> may be substituted, for example, by halogen, hydroxyl, by a trimethylsilyl, amino, nitro, cyano, carbonyl, carboxyl or a carboxyalkyl group having 1 to 5 C atoms. The invention also concerns novel pyrazole derivatives of formula (I), wherein R<1> represents a C1-C4-alkyl radical; R<2> = H, halogen or a C1-C4-alkyl radical; R<1> and R<2> together represent a five or six-membered cycloalkyl radical; R<3> = H, R<4> = C1-C20-alkyl, C3-C8-cycloalkyl; C6-C10-aryl or alkylaryl with C1-C4-alkyl and C6-C10-aryl groups and R<5> = H, C1-C20-alkyl, C3-C8-cycloalkyl, C6-C10-aryl or alkylaryl with C1-C4-alkyl and C6-C10-aryl groups.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10018604 | 2000-04-14 | ||
| DE10018604 | 2000-04-14 | ||
| PCT/EP2001/004117 WO2001079178A1 (en) | 2000-04-14 | 2001-04-10 | 1h-pyrazole derivatives, method for the production thereof and their use for inhibiting and controlling nitrification |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2001246537A1 true AU2001246537A1 (en) | 2001-10-30 |
Family
ID=7638798
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2001246537A Abandoned AU2001246537A1 (en) | 2000-04-14 | 2001-04-10 | 1h-pyrazole derivatives, method for the production thereof and their use for inhibiting and controlling nitrification |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1272472B1 (en) |
| AT (1) | ATE291014T1 (en) |
| AU (1) | AU2001246537A1 (en) |
| DE (2) | DE10117821A1 (en) |
| WO (1) | WO2001079178A1 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10224823A1 (en) * | 2002-06-05 | 2003-12-24 | Piesteritz Stickstoff | 1H-pyrazole derivatives, process for their preparation and their use as nitrification inhibitors |
| DE10343277A1 (en) | 2003-09-18 | 2005-04-21 | Piesteritz Stickstoff | N- (1H-Azolyl-methyl) amides, process for their preparation and their use as nitrification inhibitors |
| DE102008020785B4 (en) | 2008-04-25 | 2021-11-04 | Skw Stickstoffwerke Piesteritz Gmbh | Use of simple derivatives of 5-amino-1,2,4-thiadiazole to inhibit or control nitrification |
| DE102011120098B4 (en) | 2011-12-02 | 2021-02-11 | Skw Stickstoffwerke Piesteritz Gmbh | N- (1H-pyrazolyl-methyl) formamides, process for their preparation and their use as nitrification inhibitors |
| DE102017201608A1 (en) | 2017-02-01 | 2018-08-02 | Eurochem Agro Gmbh | 3,4-dimethylpyrazole-containing mixture and its use |
| CN107641057B (en) * | 2017-11-06 | 2023-10-17 | 黑龙江省农业科学院土壤肥料与环境资源研究所 | Special fertilizer for saline-alkali soil corn in cold region |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3704359A1 (en) * | 1987-02-12 | 1988-08-25 | Basf Ag | AZOLHALBAMINAL DERIVATIVES AND THEIR USE AS NITRIFICATION INHIBITORS |
| DE19631764A1 (en) * | 1996-08-06 | 1998-02-12 | Basf Ag | Use of poly acids to treat mineral fertilisers - where the fertiliser contains nitrification inhibitor in mineral fertiliser, especially new or known pyrazole compound, to reduce volatility |
| DE19822340B4 (en) * | 1998-05-19 | 2008-02-28 | Skw Stickstoffwerke Piesteritz Gmbh | Thermostable low volatility alkyl-1H-1-pyrazolylmethanamine derivatives and their use as nitrification inhibitors |
-
2001
- 2001-04-10 AU AU2001246537A patent/AU2001246537A1/en not_active Abandoned
- 2001-04-10 WO PCT/EP2001/004117 patent/WO2001079178A1/en not_active Ceased
- 2001-04-10 DE DE10117821A patent/DE10117821A1/en not_active Withdrawn
- 2001-04-10 AT AT01919446T patent/ATE291014T1/en not_active IP Right Cessation
- 2001-04-10 EP EP01919446A patent/EP1272472B1/en not_active Expired - Lifetime
- 2001-04-10 DE DE50105621T patent/DE50105621D1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO2001079178A1 (en) | 2001-10-25 |
| EP1272472B1 (en) | 2005-03-16 |
| DE50105621D1 (en) | 2005-04-21 |
| EP1272472A1 (en) | 2003-01-08 |
| DE10117821A1 (en) | 2001-10-31 |
| ATE291014T1 (en) | 2005-04-15 |
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