DE2928468C2 - - Google Patents
Info
- Publication number
- DE2928468C2 DE2928468C2 DE19792928468 DE2928468A DE2928468C2 DE 2928468 C2 DE2928468 C2 DE 2928468C2 DE 19792928468 DE19792928468 DE 19792928468 DE 2928468 A DE2928468 A DE 2928468A DE 2928468 C2 DE2928468 C2 DE 2928468C2
- Authority
- DE
- Germany
- Prior art keywords
- pyridazinone
- phenyl
- water
- amino
- dichloro
- 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.)
- Expired
Links
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- VKWCOHVAHQOJGU-UHFFFAOYSA-N 4,5-dichloro-2-phenylpyridazin-3-one Chemical compound O=C1C(Cl)=C(Cl)C=NN1C1=CC=CC=C1 VKWCOHVAHQOJGU-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- HAKJEHJYRKVCIU-UHFFFAOYSA-N 4-amino-5-chloro-2-phenylpyridazin-3-one Chemical compound O=C1C(N)=C(Cl)C=NN1C1=CC=CC=C1 HAKJEHJYRKVCIU-UHFFFAOYSA-N 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 238000010790 dilution Methods 0.000 claims description 4
- 239000012895 dilution Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- 235000010288 sodium nitrite Nutrition 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 7
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 6
- 239000005493 Chloridazon (aka pyrazone) Substances 0.000 description 5
- 239000004009 herbicide Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000002363 herbicidal effect Effects 0.000 description 3
- 238000005576 amination reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 2
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- BXQYQBFZTKKPHI-UHFFFAOYSA-M sodium;nitrite;hydrochloride Chemical compound [Na+].Cl.[O-]N=O BXQYQBFZTKKPHI-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having 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
- C07D237/14—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT8326478 | 1978-07-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2928468A1 DE2928468A1 (de) | 1980-02-07 |
| DE2928468C2 true DE2928468C2 (enrdf_load_stackoverflow) | 1988-09-08 |
Family
ID=11319752
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792928468 Granted DE2928468A1 (de) | 1978-07-28 | 1979-07-13 | Verfahren zur herstellung von 4,5- dichlor-2-phenyl-3-(2h)-pyridazinon aus 4-amino-5-chlor-2-phenyl-3(2h)-pyridazinon |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2928468A1 (enrdf_load_stackoverflow) |
-
1979
- 1979-07-13 DE DE19792928468 patent/DE2928468A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2928468A1 (de) | 1980-02-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: WEICKMANN, H., DIPL.-ING. FINCKE, K., DIPL.-PHYS. |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |