DE3126479A1 - 2'-phenylhydrazino-2-cyanacrylsaeureester, verfahren zu ihrer herstellung, diese enthaltende herbizide und ihre anwendung als herbizide - Google Patents
2'-phenylhydrazino-2-cyanacrylsaeureester, verfahren zu ihrer herstellung, diese enthaltende herbizide und ihre anwendung als herbizideInfo
- Publication number
- DE3126479A1 DE3126479A1 DE19813126479 DE3126479A DE3126479A1 DE 3126479 A1 DE3126479 A1 DE 3126479A1 DE 19813126479 DE19813126479 DE 19813126479 DE 3126479 A DE3126479 A DE 3126479A DE 3126479 A1 DE3126479 A1 DE 3126479A1
- Authority
- DE
- Germany
- Prior art keywords
- chlorine
- phenylhydrazino
- parts
- compounds
- weight
- 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.)
- Withdrawn
Links
- 239000004009 herbicide Substances 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 title abstract description 16
- 239000000460 chlorine Substances 0.000 claims abstract description 41
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 13
- -1 methylsulphonyl Chemical group 0.000 claims abstract description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims abstract description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 7
- 150000004031 phenylhydrazines Chemical class 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229940067157 phenylhydrazine Drugs 0.000 claims description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- 150000002431 hydrogen Chemical class 0.000 abstract description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 11
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
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- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 description 2
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- 238000010790 dilution Methods 0.000 description 2
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- 230000012010 growth Effects 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
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- MULHANRBCQBHII-UHFFFAOYSA-N (2,4,6-trichlorophenyl)hydrazine Chemical compound NNC1=C(Cl)C=C(Cl)C=C1Cl MULHANRBCQBHII-UHFFFAOYSA-N 0.000 description 1
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
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- KBLAMUYRMZPYLS-UHFFFAOYSA-N 2,3-bis(2-methylpropyl)naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 KBLAMUYRMZPYLS-UHFFFAOYSA-N 0.000 description 1
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- REEXLQXWNOSJKO-UHFFFAOYSA-N 2h-1$l^{4},2,3-benzothiadiazine 1-oxide Chemical compound C1=CC=C2S(=O)NN=CC2=C1 REEXLQXWNOSJKO-UHFFFAOYSA-N 0.000 description 1
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- 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
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 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
- C07D231/14—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
- C07D231/38—Nitrogen 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
- 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
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (25)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813126479 DE3126479A1 (de) | 1981-07-04 | 1981-07-04 | 2'-phenylhydrazino-2-cyanacrylsaeureester, verfahren zu ihrer herstellung, diese enthaltende herbizide und ihre anwendung als herbizide |
| AT81108815T ATE11136T1 (de) | 1980-12-05 | 1981-10-23 | 5-amino-1-phenylpyrazol-4-carbonsaeureester, verfahren zu ihrer herstellung, diese enthaltende herbizide und ihre anwendung als herbizide. |
| DE8181108815T DE3168194D1 (en) | 1980-12-05 | 1981-10-23 | 5-amino-1-phenylpyrazole-4-carboxylic acids, process for their preparation, herbicides containing them and their use as herbicides |
| EP81108816A EP0053699B1 (de) | 1980-12-05 | 1981-10-23 | 2'-Phenylhydrazino-2-cyanacrylsäureester und diese enthaltende Herbizide |
| AT81108816T ATE4705T1 (de) | 1980-12-05 | 1981-10-23 | 2'-phenylhydrazino-2-cyanacrylsaeureester und diese enthaltende herbizide. |
| EP81108815A EP0053698B1 (de) | 1980-12-05 | 1981-10-23 | 5-Amino-1-phenylpyrazol-4-carbonsäureester, Verfahren zu ihrer Herstellung, diese enthaltende Herbizide und ihre Anwendung als Herbizide |
| GR66329A GR75122B (cs) | 1980-12-05 | 1981-10-23 | |
| DE8181108816T DE3160972D1 (en) | 1980-12-05 | 1981-10-23 | 2'-phenyl-hydrazino-2-cyanacrylic-acid esters and herbicides containing them |
| GR66332A GR74695B (cs) | 1980-12-05 | 1981-10-23 | |
| US06/322,673 US4420324A (en) | 1980-12-05 | 1981-11-18 | 5-Amino-1-di-or tri-substituted phenylpyrazole-4-carboxylic acid methyl esters |
| US06/322,674 US4376645A (en) | 1980-12-05 | 1981-11-18 | 2'-Phenylhydrazino-2-cyanoacrylic acid esters and herbicides containing these compounds |
| IL64309A IL64309A0 (en) | 1980-12-05 | 1981-11-18 | 2'-phenylhydrazino-2-cyano acrylic acid esters,their manufacture and their use as herbicides |
| IL64308A IL64308A (en) | 1980-12-05 | 1981-11-18 | Herbicidal compositions containing 5-amino-1-phenylpyrazole-4-carboxylic acid esters and some novel compounds of this type |
| CA000390773A CA1176271A (en) | 1980-12-05 | 1981-11-24 | 2'-phenylhydrazino-2-cyanoacrylic acid esters and herbicides containing these compounds |
| CA000390754A CA1164879A (en) | 1980-12-05 | 1981-11-24 | 5-amino-1-phenylpyrazole-4-carboxylic acid esters, their preparation, herbicides containing these compounds and the use of these compounds as herbicides |
| DD81235152A DD201750A5 (de) | 1980-12-05 | 1981-11-26 | Herbizide mittel |
| DD81235151A DD201091A5 (de) | 1980-12-05 | 1981-11-26 | Herbizide mittel |
| CS889381A CS229644B2 (en) | 1981-07-04 | 1981-12-01 | Herbicide |
| AR287696A AR229598A1 (es) | 1980-12-05 | 1981-12-03 | Esteres 5-amino-1-fenilpirazol-4-carboxilicos,un procedimiento para la obtencion de los mismos y composiciones herbicidas que los contienen como agente activo |
| BR8107888A BR8107888A (pt) | 1980-12-05 | 1981-12-04 | Composicoes herbicidas,baseadas em derivados de acido 2'-fenilhidrazino-acrilico |
| DK537281A DK537281A (da) | 1980-12-05 | 1981-12-04 | 2!-phenylhydrazino-2-cyanoacrylsyreestere til anvendelse som herbicider |
| BR8107887A BR8107887A (pt) | 1980-12-05 | 1981-12-04 | Composicoes herbicidas,baseadas em derivados de acido aminopirazol-carboxilico |
| AU78276/81A AU7827681A (en) | 1980-12-05 | 1981-12-04 | Phenylhydrazine-2-cyano-acrylic acid esters |
| DK537181A DK537181A (da) | 1980-12-05 | 1981-12-04 | Herbicidt virkende 5-amino-1-phenylpyrazol-4-carboxylsyreestere |
| IE2850/81A IE51728B1 (en) | 1980-12-05 | 1981-12-04 | 5-amino-1-phenylpyrazole-4-carboxylic acid esters,their preparation,herbicides containing these compounds and the use of these compounds as herbicides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813126479 DE3126479A1 (de) | 1981-07-04 | 1981-07-04 | 2'-phenylhydrazino-2-cyanacrylsaeureester, verfahren zu ihrer herstellung, diese enthaltende herbizide und ihre anwendung als herbizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3126479A1 true DE3126479A1 (de) | 1983-01-27 |
Family
ID=6136146
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813126479 Withdrawn DE3126479A1 (de) | 1980-12-05 | 1981-07-04 | 2'-phenylhydrazino-2-cyanacrylsaeureester, verfahren zu ihrer herstellung, diese enthaltende herbizide und ihre anwendung als herbizide |
Country Status (2)
| Country | Link |
|---|---|
| CS (1) | CS229644B2 (cs) |
| DE (1) | DE3126479A1 (cs) |
-
1981
- 1981-07-04 DE DE19813126479 patent/DE3126479A1/de not_active Withdrawn
- 1981-12-01 CS CS889381A patent/CS229644B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS229644B2 (en) | 1984-06-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |