CS273620B2 - Herbicide and method of its active substance production - Google Patents
Herbicide and method of its active substance production Download PDFInfo
- Publication number
- CS273620B2 CS273620B2 CS705886A CS705886A CS273620B2 CS 273620 B2 CS273620 B2 CS 273620B2 CS 705886 A CS705886 A CS 705886A CS 705886 A CS705886 A CS 705886A CS 273620 B2 CS273620 B2 CS 273620B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- formula
- nitro
- malonate
- active ingredient
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 13
- 239000013543 active substance Substances 0.000 title description 4
- 239000004009 herbicide Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 22
- -1 alkaline earth metal salt Chemical class 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 239000004480 active ingredient Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical class OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- SBILOPRQKYWAQS-UHFFFAOYSA-N 3-oxo-3-(2-phenoxybenzoyl)oxypropanoic acid Chemical compound C1=CC=C(C=C1)OC2=CC=CC=C2C(=O)OC(=O)CC(=O)O SBILOPRQKYWAQS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical class CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 claims 1
- 229910001508 alkali metal halide Inorganic materials 0.000 claims 1
- 150000008045 alkali metal halides Chemical class 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- DFFDSQBEGQFJJU-UHFFFAOYSA-N butyl hydrogen carbonate Chemical compound CCCCOC(O)=O DFFDSQBEGQFJJU-UHFFFAOYSA-N 0.000 claims 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical group CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
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- 238000003756 stirring Methods 0.000 description 9
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- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
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- OAQIJHWWDSEJDY-UHFFFAOYSA-N diethyl 2-(4-fluoro-2-nitrobenzoyl)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)C(=O)C1=CC=C(F)C=C1[N+]([O-])=O OAQIJHWWDSEJDY-UHFFFAOYSA-N 0.000 description 2
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- 239000011734 sodium Substances 0.000 description 1
- IPWNRWMOCMQKDB-UHFFFAOYSA-M sodium 2-chloro-4-(trifluoromethyl)phenolate Chemical compound ClC1=C(C=CC(=C1)C(F)(F)F)[O-].[Na+] IPWNRWMOCMQKDB-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RVULBHWZFCBODE-UHFFFAOYSA-M sodium;5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical compound [Na+].C1=C([N+]([O-])=O)C(C(=O)[O-])=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 RVULBHWZFCBODE-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/48—Nitro-carboxylic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU853797A HU196884B (en) | 1985-10-01 | 1985-10-01 | Herbicides comprising phenoxy-benzoyl-malon ester derivatives as active ingredient and process for producing the active ingredients |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS705886A2 CS705886A2 (en) | 1990-08-14 |
| CS273620B2 true CS273620B2 (en) | 1991-03-12 |
Family
ID=10965547
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS705886A CS273620B2 (en) | 1985-10-01 | 1986-10-01 | Herbicide and method of its active substance production |
Country Status (14)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5925795A (en) * | 1996-09-16 | 1999-07-20 | Zeneca Limited | Processes for the preparation of aryl-β-diketones, arylpyrimidine ketones and crop protection intermediates |
-
1985
- 1985-10-01 HU HU853797A patent/HU196884B/hu not_active IP Right Cessation
-
1986
- 1986-09-08 IL IL79974A patent/IL79974A/xx unknown
- 1986-09-18 CH CH3682/86A patent/CH676595A5/de not_active IP Right Cessation
- 1986-09-24 DE DE19863632492 patent/DE3632492A1/de not_active Withdrawn
- 1986-09-25 DD DD86294689A patent/DD249840A5/de not_active IP Right Cessation
- 1986-09-25 DD DD86301113A patent/DD255729A5/de not_active IP Right Cessation
- 1986-09-30 FR FR8613597A patent/FR2587998B1/fr not_active Expired
- 1986-09-30 JP JP61230188A patent/JPS6281353A/ja active Pending
- 1986-09-30 SU SU864028283A patent/SU1676435A3/ru active
- 1986-09-30 SE SE8604148A patent/SE8604148L/ not_active Application Discontinuation
- 1986-09-30 GB GB8623486A patent/GB2181133B/en not_active Expired
- 1986-09-30 AU AU63266/86A patent/AU595834B2/en not_active Ceased
- 1986-10-01 NL NL8602481A patent/NL8602481A/nl not_active Application Discontinuation
- 1986-10-01 BE BE0/217241A patent/BE905534A/fr not_active IP Right Cessation
- 1986-10-01 CS CS705886A patent/CS273620B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL79974A0 (en) | 1986-12-31 |
| FR2587998A1 (fr) | 1987-04-03 |
| HUT41590A (en) | 1987-05-28 |
| CH676595A5 (enrdf_load_stackoverflow) | 1991-02-15 |
| GB2181133B (en) | 1989-03-22 |
| FR2587998B1 (fr) | 1988-08-05 |
| NL8602481A (nl) | 1987-05-04 |
| GB8623486D0 (en) | 1986-11-05 |
| DE3632492A1 (de) | 1987-04-16 |
| AU6326686A (en) | 1987-04-09 |
| BE905534A (fr) | 1987-02-02 |
| AU595834B2 (en) | 1990-04-12 |
| JPS6281353A (ja) | 1987-04-14 |
| DD249840A5 (de) | 1987-09-23 |
| SE8604148L (sv) | 1987-04-02 |
| SE8604148D0 (sv) | 1986-09-30 |
| HU196884B (en) | 1989-02-28 |
| SU1676435A3 (ru) | 1991-09-07 |
| GB2181133A (en) | 1987-04-15 |
| CS705886A2 (en) | 1990-08-14 |
| DD255729A5 (de) | 1988-04-13 |
| IL79974A (en) | 1990-09-17 |
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