DE1543217B1 - 2,6-Dinitro-4-alkylphenol esters and their use in fungicidal agents - Google Patents
2,6-Dinitro-4-alkylphenol esters and their use in fungicidal agentsInfo
- Publication number
- DE1543217B1 DE1543217B1 DE19651543217 DE1543217A DE1543217B1 DE 1543217 B1 DE1543217 B1 DE 1543217B1 DE 19651543217 DE19651543217 DE 19651543217 DE 1543217 A DE1543217 A DE 1543217A DE 1543217 B1 DE1543217 B1 DE 1543217B1
- Authority
- DE
- Germany
- Prior art keywords
- dinitrophenyl
- hexyl
- ethyl
- crotonate
- dinitro
- 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.)
- Granted
Links
- 239000000417 fungicide Substances 0.000 title claims description 4
- 150000002148 esters Chemical class 0.000 title description 6
- -1 4- (1-n-propyl-n-pentyl) -2,6-dinitrophenyl Chemical group 0.000 claims description 27
- 241000221785 Erysiphales Species 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- BYFMHWHQZPWKQA-UHFFFAOYSA-N CCCCCC(CC)C1=CC([N+]([O-])=O)=C(OC(=O)C(C)=C)C([N+]([O-])=O)=C1 Chemical compound CCCCCC(CC)C1=CC([N+]([O-])=O)=C(OC(=O)C(C)=C)C([N+]([O-])=O)=C1 BYFMHWHQZPWKQA-UHFFFAOYSA-N 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 6
- 241000209219 Hordeum Species 0.000 description 6
- 235000007340 Hordeum vulgare Nutrition 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- KQEDZYSQYRALEB-QHHAFSJGSA-N (E)-2-(2,6-dinitrophenyl)but-2-enoic acid Chemical compound C/C=C(\C1=C(C=CC=C1[N+](=O)[O-])[N+](=O)[O-])/C(=O)O KQEDZYSQYRALEB-QHHAFSJGSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 206010039509 Scab Diseases 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000008029 eradication Effects 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- YTUQXGGWNCHKOJ-UHFFFAOYSA-N (2,6-dinitro-4-nonylphenyl) butanoate Chemical compound CCCCCCCCCC1=CC([N+]([O-])=O)=C(OC(=O)CCC)C([N+]([O-])=O)=C1 YTUQXGGWNCHKOJ-UHFFFAOYSA-N 0.000 description 1
- DRNFDNXPTCNHIV-UHFFFAOYSA-N (2,6-dinitro-4-octan-3-ylphenyl) prop-2-enoate Chemical compound C(C=C)(=O)OC1=C(C=C(C=C1[N+](=O)[O-])C(CCCCC)CC)[N+](=O)[O-] DRNFDNXPTCNHIV-UHFFFAOYSA-N 0.000 description 1
- KLZNCAYLXQDTIK-UHFFFAOYSA-N (2,6-dinitrophenyl) benzoate Chemical compound [O-][N+](=O)c1cccc(c1OC(=O)c1ccccc1)[N+]([O-])=O KLZNCAYLXQDTIK-UHFFFAOYSA-N 0.000 description 1
- 125000003456 2,6-dinitrophenyl group Chemical group [H]C1=C([H])C(=C(*)C(=C1[H])[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
- RQQGKHZHIROOGO-UHFFFAOYSA-N 2-(2,6-dinitrophenyl)acetic acid Chemical compound OC(=O)CC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O RQQGKHZHIROOGO-UHFFFAOYSA-N 0.000 description 1
- YEKTTWKHFNBULP-UHFFFAOYSA-N C(C)(=O)OC1=C(C=C(C=C1[N+](=O)[O-])C(CCCCC)CC)[N+](=O)[O-] Chemical compound C(C)(=O)OC1=C(C=C(C=C1[N+](=O)[O-])C(CCCCC)CC)[N+](=O)[O-] YEKTTWKHFNBULP-UHFFFAOYSA-N 0.000 description 1
- PXRHGLSNOCAFPA-UHFFFAOYSA-N C=C(C(O)=O)C(C([N+]([O-])=O)=CC=C1)=C1[N+]([O-])=O Chemical compound C=C(C(O)=O)C(C([N+]([O-])=O)=CC=C1)=C1[N+]([O-])=O PXRHGLSNOCAFPA-UHFFFAOYSA-N 0.000 description 1
- QGIVAEUWQXCBKT-UHFFFAOYSA-N CCCCCC(CC)C(C=C1[N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(C1=CC=CC=C1)=O Chemical compound CCCCCC(CC)C(C=C1[N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(C1=CC=CC=C1)=O QGIVAEUWQXCBKT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 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
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical class OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical class C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-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
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/39—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups
- C07C205/42—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/43—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Die Erfindung betrifft Ester von 2,6-Dinitro-4-aIkylphenolen, nämlichThe invention relates to esters of 2,6-dinitro-4-alkylphenols, viz
1. 4-(l-n-Propyl-n-butyl)-2,6-dinitrophenylcrotonat, 1. 4- (l-n-propyl-n-butyl) -2,6-dinitrophenyl crotonate,
2. 4-(l-n-Propyl-n-pentyl)-2,6-dinitrophenylcrotonat, 2. 4- (l-n-propyl-n-pentyl) -2,6-dinitrophenyl crotonate,
3. 4-(l-Äthyl-n-pentyI)-2,6-dinitrophenyl-crotonat,3. 4- (1-ethyl-n-pentyI) -2,6-dinitrophenyl crotonate,
4. 4-( 1 -Äthyl-n-hexyl)-2,6-dinitrophenyl-acetat,4. 4- (1-ethyl-n-hexyl) -2,6-dinitrophenyl acetate,
5. 4-( 1 -ÄthyI-n-hexyl)-2,6-dinitrophenyl-isobutyrat,5. 4- (1-EthyI-n-hexyl) -2,6-dinitrophenyl isobutyrate,
6. 4-( 1 -Äthyl-n-hexyl)-2,6-dinitrophenyI-acrylat,6. 4- (1-ethyl-n-hexyl) -2,6-dinitrophenyl acrylate,
7. 4-( 1 -Äthyl-n-hexyl^o-dinitrophenyl-methacrylat. 7. 4- (1-Ethyl-n-hexyl ^ o-dinitrophenyl methacrylate.
8. 4-(l-Äthyl-n-hexyl)-2,6-dinitrophenyl-/?,/>-dimethylacrylat,
9. 4-(l-Äthyl-n-hexyl)-2,6-dinitrophenyl-benzoat,8. 4- (l-ethyl-n-hexyl) -2,6-dinitrophenyl - /?, /> - dimethylacrylate,
9. 4- (l-ethyl-n-hexyl) -2,6-dinitrophenyl benzoate,
10. 4-(l-Äthyl-n-hexyl)-2,6-dinitrophenyl-a-chlorpropionat, 10. 4- (l-ethyl-n-hexyl) -2,6-dinitrophenyl-a-chloropropionate,
11. 4-( 1 -Äthyl-n-hexyl )-2,6-dinitrophenyl-^-chlorpropionat, 11. 4- (1-ethyl-n-hexyl) -2,6-dinitrophenyl - ^ - chloropropionate,
12. 4-(l-n-Propyl-n-hexyl)-2,6-dinitrophenylcrotonat, 12. 4- (l-n-propyl-n-hexyl) -2,6-dinitrophenyl crotonate,
13. 4-(l-n-Butyl-n-hexyl)-2,6-dinitrophenyl-crotonat,13. 4- (l-n-Butyl-n-hexyl) -2,6-dinitrophenyl crotonate,
14. 4-(l-n-Pentyl-n-hexyl)-2,6-dinitrophenyl-crotonat14. 4- (1-n-Pentyl-n-hexyl) -2,6-dinitrophenyl crotonate
mit den folgenden Kennwerten:with the following characteristics:
und ihre Verwendung als Wirkstoffe in fungiziden Mitteln, insbesondere zur Bekämpfung von Mehltau. Ester von 2,6-Dinitro-4-alkylphenolen mit gesättigten und ungesättigten Carbonsäuren sind bereits bekannt (vgl. die USA.-Patentschrift 2526 660, in der unter anderem Crotonsäureester des 4-Capryl-2,6-dinitro-phenols beschrieben ist). In der USA.-Patentschrift 2 861915 werden die 4-Pentensäureester, in der USA.-Patentschrift 2862022 (entsprechend deutscher Ausiegeschrift 1 053 859) die Methacrylsäureester, in der deutschen Auslegeschrift 035 960 die Sorbinsäureester und in der britischen Patentschrift 935 398 die Alkansäureester von 4-Alkyl-2,6-dinitrophenolen beschrieben.and their use as active ingredients in fungicidal agents, in particular for combating powdery mildew. Esters of 2,6-dinitro-4-alkylphenols with saturated and unsaturated carboxylic acids are already available known (see. The USA. Patent 2526 660, in which, inter alia, crotonic acid ester of 4-caprylic-2,6-dinitro-phenol is described). In the United States patent 2 861915 the 4-pentenoic acid esters, in U.S. Patent 2862022 (corresponding to German Ausiegeschrift 1 053 859) the methacrylic acid esters, in the German Ausiegeschrift 035 960 the sorbic acid esters and in British Patent 935 398 the alkanoic acid esters of 4-alkyl-2,6-dinitrophenols are described.
ORIGINAL INSPECTEDORIGINAL INSPECTED
Die Phytotoxizität der Ester gemäß der Erfindung ist geringer als die der entsprechenden Stamm-2,6-dinitro-4-alkylphenole. The phytotoxicity of the esters according to the invention is less than that of the corresponding parent 2,6-dinitro-4-alkylphenols.
Die neuen Verbindungen gemäß der Erfindung können hergestellt werden, indem man in an sich bekannter Weise das entsprechende 2,6-Dinitro-4-alkylphenol oder ein funktionelles Derivat dieses Phenols mit einem Acylierungsderivat der entsprechenden Säure verestert. Vorzugsweise wird ein Alkaliphenoxyd, beispielsweise das Natrium- oder Kaliumphenoxyd, des Phenols in Lösung in einem inerten organischen Lösungsmittel mit einem Halogenid der Säure umgesetzt. The new compounds according to the invention can be prepared by using a method known per se Put the corresponding 2,6-dinitro-4-alkylphenol or a functional derivative of this phenol with esterified with an acylation derivative of the corresponding acid. Preferably an alkali phenoxide, for example sodium or potassium phenoxide, of phenol in solution in an inert organic Solvent reacted with a halide of the acid.
Die in diesem Verfahren als Ausgangsmaterialien verwendeten Dinitroalkylphenole können durch Dinitrieren der entsprechenden Alkylphenole in an sich bekannter Weise erhalten werden. Vorzugsweise wird das 4-Alkylphenol in Lösung in einem inerten organischen Lösungsmittel, insbesondere einem Kohlenwasserstoff oder einem halogenierten Kohlenwasserstoff, unter Rühren zu wäßriger Salpetersäure, die wenigstens 2 Äquivalente Schwefelsäure enthält, zugesetzt, nach Beendigung der Zugabe die Temperatur des Reaktionsgemisches erhöht, um die Nitrierung zu Ende zu führen, nach Beendigung der Umsetzung das Reaktionsgemisch gekühlt und das nitrierte Phenol von dem Reaktionsgemisch abgetrennt.The dinitroalkylphenols used as starting materials in this process can be obtained by dinitration the corresponding alkylphenols can be obtained in a manner known per se. Preferably will the 4-alkylphenol in solution in an inert organic Solvents, in particular a hydrocarbon or a halogenated hydrocarbon, added with stirring to aqueous nitric acid containing at least 2 equivalents of sulfuric acid, after the addition has ended, the temperature of the reaction mixture is increased in order to end the nitration to lead, after completion of the reaction, the reaction mixture is cooled and the nitrated phenol separated from the reaction mixture.
Die für die Herstellung der 2,6-Dinitroalkylphenole verwendeten 4-Alkylphenole können hergestellt werden, indem man ein p-Hydroxybenzoketon mit dem entsprechenden Alkylmagnesiumhalogenid umsetzt, so daß ein tertiäres Carbinol erhalten wird, das Carbinol dehydratisiert und das gebildete^ Olefin dann, beispielsweise unter Verwendung von Palladium/Aktivkohle in Äthanol, katalytisch hydriert. For the production of the 2,6-Dinitroalkylphenole 4-alkylphenols used can be produced by reacting a p-hydroxybenzoketone with the corresponding alkyl magnesium halide, so that a tertiary carbinol is obtained, the carbinol is dehydrated and the olefin formed then catalytically hydrogenated, for example using palladium / activated carbon in ethanol.
Die Dehydratation kann beim Erwärmen spontan erfolgen oder durch Verwendung eines sauren Katalysators, beispielsweise Kaliumhydrogensulfat, p-Toluolsulfonsäure oder Schwefelsäure, herbeigeführt werden. Bei Anwendung eines solchen Verfahrens wird erreicht, daß die 4-Alkylgruppe genau die gewünschte Verzweigung aufweist. In manchen Fällen kann es vorteilhaft sein, den Methyläther des Benzoketons zu verwenden, um die Löslichkeit in dem für die Umsetzung verwendeten Lösungsmittel zu verbessern und bzw. oder Nebenreaktionen zu vermeiden, wobei das Produkt der Reduktion des Olefins dann demethyliert werden muß.Dehydration can occur spontaneously when heated or by using an acidic one Catalyst, for example potassium hydrogen sulfate, p-toluenesulfonic acid or sulfuric acid, brought about will. Using such a method it is achieved that the 4-alkyl group does exactly that has desired branching. In some cases it can be beneficial to use the methyl ether of the benzoketone to be used to improve the solubility in the solvent used for the reaction and / or to avoid side reactions, the product being the reduction of the olefin then has to be demethylated.
Die Verbindungen gemäß der Erfindung können mit einem flüssigen oder festen Träger oder Verdünnungsmittel und gewünschtenfalls weiteren Wirkstoffen, beispielsweise anderen Fungiziden oder mit Akariziden oder Insektiziden und Netz-, Dispergier- oder Emulgiermitteln zu Schädlingsbekämpfungsmitteln in der Form von Lösungen, Emulsionen oder Aerosolen, Stäuben, netzbaren Pulvern, Granulaten, Pellets oder Pasten, oder zu Raucherzeugern, die die Verbindung zusammen mit einer festen pyrotechnischen Komponente enthalten, verarbeitet werden.The compounds according to the invention can be mixed with a liquid or solid carrier or diluent and, if desired, further active ingredients, for example other fungicides or with Acaricides or insecticides and wetting agents, dispersants or emulsifiers for pesticides in the form of solutions, emulsions or aerosols, dusts, wettable powders, granulates, Pellets or pastes, or to make smoke generators that connect together with a solid pyrotechnic Component included, are processed.
Die Ester gemäß der Erfindung wirken insbesondere gegen Mehltau und zwar zumindest gegen Apfelmehltau oder Gerstenmehltau. Beispielsweise haben die obigen Verbindungen 4 und 5 LD95-Werte von 50 bzw. 35 ppm gegen Sporen von Venturia inaequalis, den Erreger des Apfelschorfs und ergeben eine 99%ige Ausrottung von Apfelschorf bei einer Konzentration von 300 ppm.The esters according to the invention are particularly effective against powdery mildew, at least against apple powdery mildew or barley powdery mildew. For example, the above compounds 4 and 5 have LD 95 values of 50 and 35 ppm, respectively, against spores of Venturia inaequalis, the causative agent of apple scab, and result in 99% eradication of apple scab at a concentration of 300 ppm.
Prüfung gegen GerstenmehltauTesting against barley powdery mildew
Töpfe mit je 10 Gerstensämlingen wurden in sechs Gruppen gehalten, wobei jede Gruppe je einen Topf für jede Behandlung enthielt. Die Sämlinge wurden infiziert, indem man Sporen von infizierten Pflanzen darüberblies, nachdem alle Blätter mit Ausnahme des ältesten von jeder Pflanze entfernt waren.Pots with 10 barley seedlings each were kept in six groups, with each group having one pot for each treatment included. The seedlings were infected by taking spores from infected plants blew over it after removing all but the oldest leaves from each plant.
Nachdem die Infektion sich ausreichend entwickelt hatte, wurde die anwesende Menge Mehltau ermittelt, indem man die Blätter wie folgt bewertete:After the infection had developed sufficiently, the amount of powdery mildew present was determined, by evaluating the leaves as follows:
0 = kein Mehltau anwesend0 = no powdery mildew present
1 = 0 bis 3% der Blattfläche mit Mehltau1 = 0 to 3% of the leaf area with powdery mildew
infiziertinfected
2 = 4 bis 7% der Blattfläche mit Mehltau2 = 4 to 7% of the leaf area with powdery mildew
infiziertinfected
3 = 8 bis 17% der Blattfläche mit Mehltau3 = 8 to 17% of the leaf area with powdery mildew
infiziertinfected
4 = 18 bis 41% der Blattfläche mit Mehltau4 = 18 to 41% of the leaf area with powdery mildew
infiziertinfected
5 = 42 bis 100% der Blattfläche mit Mehltau5 = 42 to 100% of the leaf area with powdery mildew
infiziertinfected
Dann wurden die Pflanzen 15 Sekunden lang in eine Lösung mit einer Wirkstoffkonzentration von 20 ppm und einer Konzentration an Natriumdioctylsulfosuccinat von 300 ppm getaucht.The plants were then immersed for 15 seconds Solution with an active ingredient concentration of 20 ppm and a concentration of sodium dioctyl sulfosuccinate submerged at 300 ppm.
Nach der Behandlung wurden die Pflanzen 4 Tage in einem kühlen Gewächshaus gehalten, wonach sie nach der obigen Bewertungsskala bewertet wurden. Nur aktiver Mehltau wurde bewertet.After the treatment, the plants were kept in a cool greenhouse for 4 days, after which they were rated according to the above rating scale. Only active powdery mildew was assessed.
Für jede Versuchspflanze wurde die mittlere Bewertungsziffer je Blatt ermittelt, und diese Bewertungsziffern wurden für eine statistische Analyse verwendet. Die prozentuale Ausrottung wurde berechnet, indem man die mittlere Bewertungsziffer je Blatt (der sechs Versuchspflanzen kombiniert) mit der mittleren Bewertungsziffer je Blatt der unbehandelten Sämlinge verglich.The mean evaluation number per leaf was determined for each test plant, and these evaluation numbers were used for statistical analysis. Percent eradication was calculated by the mean evaluation number per leaf (of the six test plants combined) with the mean evaluation number compared per leaf of the untreated seedlings.
Die Ergebnisse sind in der folgenden Tabelle zusammengestellt: The results are summarized in the following table:
mehltau, %of barley
powdery mildew,%
Fortsetzungcontinuation
mehltau, %of barley
powdery mildew,%
von Gersten
mehltau, %
20 ppmextermination
of barley
powdery mildew,%
20 ppm
substanzen
DComparison
substances
D.
phenyl-butyrat
(bekannt aus britischer
Patentschrift 935 398)4-nonyl-2,6-dinitro-
phenyl butyrate
(known from British
Patent specification 935 398)
Die Wirkung einiger Verbindungen gemäß der Erfindung gegen Apfelmehltau war wie folgt:The action of some compounds according to the invention against apple powdery mildew was as follows:
ppmtration,
ppm
mehltauof apple
mildew
ORIGINAL INSPECTEDORIGINAL INSPECTED
Claims (15)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3203264A GB1113783A (en) | 1964-08-06 | 1964-08-06 | Improvements in or relating to esters of 4-alkyl-2,6-dinitrophenols and pesticides containing them |
| GB3203264 | 1964-08-06 | ||
| GB2989065 | 1965-07-14 | ||
| GB2989065 | 1965-07-14 | ||
| DEM0066192 | 1965-08-02 | ||
| US6758370A | 1970-08-27 | 1970-08-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1543217B1 true DE1543217B1 (en) | 1972-06-29 |
| DE1543217C DE1543217C (en) | 1973-01-25 |
Family
ID=
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2526660A (en) * | 1946-07-06 | 1950-10-24 | Rohm & Haas | Capryldintrophenyl crotonate |
| DE1035960B (en) * | 1956-06-22 | 1958-08-07 | Hoechst Ag | Pest control agents, especially with acaricidal and ovicidal effects |
| US2861915A (en) * | 1956-06-01 | 1958-11-25 | Rohm & Haas | Dinitrophenyl 4-pentenoates |
| US2862022A (en) * | 1956-06-01 | 1958-11-25 | Rohm & Haas | Dinitroalkylphenyl methacrylates |
| DE1053859B (en) * | 1956-06-01 | 1959-03-26 | Rohm & Haas | Pest repellants |
| GB935398A (en) * | 1961-06-02 | 1963-08-28 | R I A F Societa Azionaria Roma | Process for preparing esters of alkyl nitrophenols useful as fungicides |
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2526660A (en) * | 1946-07-06 | 1950-10-24 | Rohm & Haas | Capryldintrophenyl crotonate |
| US2861915A (en) * | 1956-06-01 | 1958-11-25 | Rohm & Haas | Dinitrophenyl 4-pentenoates |
| US2862022A (en) * | 1956-06-01 | 1958-11-25 | Rohm & Haas | Dinitroalkylphenyl methacrylates |
| DE1053859B (en) * | 1956-06-01 | 1959-03-26 | Rohm & Haas | Pest repellants |
| DE1071410B (en) * | 1956-06-01 | 1960-06-02 | Rohm & Haas Company, Philadelphia, Pa. (V. St. A.) | Pesticides. 31I. 5. 57th V. St. America |
| DE1035960B (en) * | 1956-06-22 | 1958-08-07 | Hoechst Ag | Pest control agents, especially with acaricidal and ovicidal effects |
| GB935398A (en) * | 1961-06-02 | 1963-08-28 | R I A F Societa Azionaria Roma | Process for preparing esters of alkyl nitrophenols useful as fungicides |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1113783A (en) | 1968-05-15 |
| NL6510269A (en) | 1966-02-07 |
| CH516278A (en) | 1971-12-15 |
| IL24078A (en) | 1970-12-24 |
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