DE1542993C3 - Verwendung von N-Cyanoalkylchloracetamiden als Pflanzenfungizide - Google Patents
Verwendung von N-Cyanoalkylchloracetamiden als PflanzenfungizideInfo
- Publication number
- DE1542993C3 DE1542993C3 DE1542993A DE1542993A DE1542993C3 DE 1542993 C3 DE1542993 C3 DE 1542993C3 DE 1542993 A DE1542993 A DE 1542993A DE 1542993 A DE1542993 A DE 1542993A DE 1542993 C3 DE1542993 C3 DE 1542993C3
- Authority
- DE
- Germany
- Prior art keywords
- chloroacetamides
- cyanoalkyl
- plants
- powdery mildew
- plant
- 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
- 239000000417 fungicide Substances 0.000 title claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 241000221785 Erysiphales Species 0.000 claims description 11
- 241000233866 Fungi Species 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 16
- 240000008067 Cucumis sativus Species 0.000 description 9
- 206010061217 Infestation Diseases 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- 241000317981 Podosphaera fuliginea Species 0.000 description 6
- 230000006735 deficit Effects 0.000 description 6
- 235000009849 Cucumis sativus Nutrition 0.000 description 5
- -1 alkyl radical Chemical class 0.000 description 5
- 238000011835 investigation Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 240000007594 Oryza sativa Species 0.000 description 3
- 231100000674 Phytotoxicity Toxicity 0.000 description 3
- 244000171263 Ribes grossularia Species 0.000 description 3
- 235000002357 Ribes grossularia Nutrition 0.000 description 3
- 240000006677 Vicia faba Species 0.000 description 3
- 235000002096 Vicia faba var. equina Nutrition 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000010410 dusting Methods 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 241001051088 Sphaerotheca humuli Species 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- WECIKJKLCDCIMY-UHFFFAOYSA-N 2-chloro-n-(2-cyanoethyl)acetamide Chemical compound ClCC(=O)NCCC#N WECIKJKLCDCIMY-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920006266 Vinyl film Polymers 0.000 description 1
- UOCSGYATURFZKY-UHFFFAOYSA-N acetamide;chloroethane Chemical compound CCCl.CC(O)=N UOCSGYATURFZKY-UHFFFAOYSA-N 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- AGSPXMVUFBBBMO-UHFFFAOYSA-N beta-aminopropionitrile Chemical compound NCCC#N AGSPXMVUFBBBMO-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical class Cl* 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 235000021186 dishes Nutrition 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- TXSXJLMEOQAASX-QHHAFSJGSA-N phenyl (e)-but-2-enoate Chemical compound C\C=C\C(=O)OC1=CC=CC=C1 TXSXJLMEOQAASX-QHHAFSJGSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4378565 | 1965-07-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1542993A1 DE1542993A1 (de) | 1970-07-23 |
| DE1542993B2 DE1542993B2 (de) | 1973-10-18 |
| DE1542993C3 true DE1542993C3 (de) | 1974-05-16 |
Family
ID=12673395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1542993A Expired DE1542993C3 (de) | 1965-07-21 | 1966-07-20 | Verwendung von N-Cyanoalkylchloracetamiden als Pflanzenfungizide |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3442929A (OSRAM) |
| DE (1) | DE1542993C3 (OSRAM) |
| DK (1) | DK111223B (OSRAM) |
| GB (1) | GB1090608A (OSRAM) |
| NL (1) | NL6610214A (OSRAM) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3102068A (en) * | 1961-10-10 | 1963-08-27 | Michigan State University Of A | Method of controlling bacterial diseases of fruit trees |
-
1966
- 1966-07-18 GB GB32127/66A patent/GB1090608A/en not_active Expired
- 1966-07-19 US US566236A patent/US3442929A/en not_active Expired - Lifetime
- 1966-07-20 NL NL6610214A patent/NL6610214A/xx unknown
- 1966-07-20 DK DK376466AA patent/DK111223B/da unknown
- 1966-07-20 DE DE1542993A patent/DE1542993C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL6610214A (OSRAM) | 1967-01-23 |
| US3442929A (en) | 1969-05-06 |
| DK111223B (da) | 1968-07-01 |
| GB1090608A (en) | 1967-11-08 |
| DE1542993A1 (de) | 1970-07-23 |
| DE1542993B2 (de) | 1973-10-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2919511A1 (de) | 2,4-disubstituierte-5-thiazolcarbonsaeuren und deren derivate, sowie ihre verwendung als schutzstoffe gegen herbizidschaeden | |
| DE2433680A1 (de) | 2,3-dihydro-2,2-dimethyl-7-benzofuranylmethylcarbamat-n-aminosulfenyl-derivate, verfahren zu deren herstellung und diese verbindungen enthaltende insektizide zusammensetzungen | |
| DE2603877C2 (de) | Oxadiazolinonverbindungen, ihre Herstellung und sie enthaltendes Mittel | |
| DE2509416C2 (de) | Dinitrobenzotrifluoride, Verfahren zu deren Herstellung und diese enthaltende pestizide Zusammensetzungen | |
| DE1542993C3 (de) | Verwendung von N-Cyanoalkylchloracetamiden als Pflanzenfungizide | |
| DE2265535C3 (de) | Herbizide Mittel und ihre Verwendung als Pflanzenwuchsregler | |
| DE3144526C2 (OSRAM) | ||
| DE2147873C2 (de) | Verfahren zur Unkrautbekämpfung mit Hilfe von 6-Nitrophenolestern | |
| DE1567153C3 (de) | Neue N-Carbamoyloxydicarbonsäureimide | |
| DE2061133A1 (de) | Pestizide Verbindung,Verfahren zu ihrer Herstellung und Verwendung | |
| DE3785704T2 (de) | Substituiertes benzimidazolfungizid. | |
| DE2605828A1 (de) | Phenoxybenzylester von spirocarbonsaeuren | |
| DE2104857C3 (de) | N-Benzylcarboxamide, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide | |
| DE1161078B (de) | Mittel zur Bekaempfung von Insekten, Spinnen und Milben, deren Eiern und von Pilzen | |
| DE2167007C3 (de) | Phosphortionamidate mit herbizider Wirkung | |
| DE2342073C3 (de) | Verwendung von Bis-(trialkylzinn)oxiden zur Bekämpfung von Milben auf Nutzpflanzen | |
| CH624961A5 (OSRAM) | ||
| DE1939010C3 (de) | Aryloxymonothioessigsäureester und ihre Verwendung als herbicide Mittel | |
| DE2739098C2 (OSRAM) | ||
| DE2027058C3 (de) | N-acylierte Carbamate, Verfahren zur Herstellung derselben und diese Verbindungen enthaltende Schädlingsbekämpfungsmittel | |
| DE2260763B2 (de) | Bekämpfung von schädlichen Organismen mit Dihalogenpropansulfonsäureesterderivaten | |
| AT339089B (de) | Schadlingsbekampfungsmittel | |
| DE2319778A1 (de) | Neue thioureidobenzolverbindungen, herstellung dieser verbindungen und milbentoetendes und fungizides mittel | |
| DE2748450A1 (de) | Neue benzoyl-n'-trichloraethylidenhydrazine und neue fungizide zubereitungen | |
| AT261313B (de) | Verfahren zur Bekämpfung von phytopathogenen Pilzen oder erdbewohnenden Nematoden |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |