DE1567157C3 - Carbonsäurehydrazide, Verfahren zu deren Herstellung, sowie deren Verwendung als Saatgutbehandlungsmittel - Google Patents
Carbonsäurehydrazide, Verfahren zu deren Herstellung, sowie deren Verwendung als SaatgutbehandlungsmittelInfo
- Publication number
- DE1567157C3 DE1567157C3 DE19651567157 DE1567157A DE1567157C3 DE 1567157 C3 DE1567157 C3 DE 1567157C3 DE 19651567157 DE19651567157 DE 19651567157 DE 1567157 A DE1567157 A DE 1567157A DE 1567157 C3 DE1567157 C3 DE 1567157C3
- Authority
- DE
- Germany
- Prior art keywords
- carboxylic acid
- acid hydrazides
- general formula
- phenylhydrazide
- seed treatment
- 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
- 238000000034 method Methods 0.000 title claims description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title claims description 5
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 title claims description 5
- 239000003795 chemical substances by application Substances 0.000 title description 7
- 238000011282 treatment Methods 0.000 title description 5
- 239000004480 active ingredient Substances 0.000 claims description 14
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 claims description 7
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 239000005745 Captan Substances 0.000 claims description 4
- 229940117949 captan Drugs 0.000 claims description 4
- 241000233866 Fungi Species 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 231100000419 toxicity Toxicity 0.000 claims description 3
- 230000001988 toxicity Effects 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052753 mercury Inorganic materials 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 230000003071 parasitic effect Effects 0.000 claims description 2
- 150000004031 phenylhydrazines Chemical class 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 229960002447 thiram Drugs 0.000 claims 2
- 239000000417 fungicide Substances 0.000 claims 1
- 231100000086 high toxicity Toxicity 0.000 claims 1
- 235000021110 pickles Nutrition 0.000 claims 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 206010061217 Infestation Diseases 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 229940005605 valeric acid Drugs 0.000 description 5
- 244000075850 Avena orientalis Species 0.000 description 4
- 235000007319 Avena orientalis Nutrition 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ZNJWOBGDQWUAKX-UHFFFAOYSA-N CCCCC(N(C(C=C1Cl)=CC=C1Cl)N)=O Chemical compound CCCCC(N(C(C=C1Cl)=CC=C1Cl)N)=O ZNJWOBGDQWUAKX-UHFFFAOYSA-N 0.000 description 2
- 241000209219 Hordeum Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- 241001459558 Monographella nivalis Species 0.000 description 2
- 241000228454 Pyrenophora graminea Species 0.000 description 2
- 241000514371 Ustilago avenae Species 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 125000000068 chlorophenyl group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- YMJSQPNVQRHZDW-UHFFFAOYSA-N (3,4-dichlorophenyl)hydrazine Chemical compound NNC1=CC=C(Cl)C(Cl)=C1 YMJSQPNVQRHZDW-UHFFFAOYSA-N 0.000 description 1
- -1 4-chlorophenyl- Chemical group 0.000 description 1
- FCCBBYPEQBSEPJ-UHFFFAOYSA-N C(CCCC)(=O)N(C1=CC=C(C=C1)[N+](=O)[O-])N Chemical compound C(CCCC)(=O)N(C1=CC=C(C=C1)[N+](=O)[O-])N FCCBBYPEQBSEPJ-UHFFFAOYSA-N 0.000 description 1
- DUKYJDJRPZQGFR-UHFFFAOYSA-N C=CC(N(C(C=C1)=CC(Cl)=C1Cl)N)=O Chemical compound C=CC(N(C(C=C1)=CC(Cl)=C1Cl)N)=O DUKYJDJRPZQGFR-UHFFFAOYSA-N 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241000221566 Ustilago Species 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000001609 comparable effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESC037720 | 1965-09-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1567157A1 DE1567157A1 (de) | 1969-10-09 |
| DE1567157B2 DE1567157B2 (de) | 1974-02-21 |
| DE1567157C3 true DE1567157C3 (de) | 1974-10-03 |
Family
ID=7434415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651567157 Expired DE1567157C3 (de) | 1965-09-14 | 1965-09-14 | Carbonsäurehydrazide, Verfahren zu deren Herstellung, sowie deren Verwendung als Saatgutbehandlungsmittel |
Country Status (7)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9206803A (pt) * | 1991-11-22 | 1995-05-02 | Uniroyal Chemical Ltd | Derivados inseticidas de fenilhidrazina |
| FR2754254B1 (fr) * | 1996-10-09 | 1998-10-30 | Rhone Poulenc Agrochimie | Fongicides a groupes hydroximiques et hydrazoniques |
-
1965
- 1965-09-14 DE DE19651567157 patent/DE1567157C3/de not_active Expired
-
1966
- 1966-08-23 BE BE685849D patent/BE685849A/xx unknown
- 1966-08-30 ES ES0330752A patent/ES330752A1/es not_active Expired
- 1966-08-30 GB GB3865566A patent/GB1085697A/en not_active Expired
- 1966-09-04 IL IL2644366A patent/IL26443A/xx unknown
- 1966-09-09 LU LU51918A patent/LU51918A1/xx unknown
- 1966-09-13 NL NL6612874A patent/NL153520B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1085697A (en) | 1967-10-04 |
| NL153520B (nl) | 1977-06-15 |
| NL6612874A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-03-15 |
| ES330752A1 (es) | 1967-06-16 |
| IL26443A (en) | 1970-05-21 |
| LU51918A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-11-09 |
| BE685849A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-02-23 |
| DE1567157A1 (de) | 1969-10-09 |
| DE1567157B2 (de) | 1974-02-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |