DE709435C - - Google Patents
Info
- Publication number
- DE709435C DE709435C DENDAT709435D DE709435DA DE709435C DE 709435 C DE709435 C DE 709435C DE NDAT709435 D DENDAT709435 D DE NDAT709435D DE 709435D A DE709435D A DE 709435DA DE 709435 C DE709435 C DE 709435C
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- coch
- groups
- aliphatic
- acid esters
- 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.)
- Active
Links
- 150000001875 compounds Chemical class 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- 230000000749 insecticidal Effects 0.000 claims description 5
- 239000002917 insecticide Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000468 ketone group Chemical group 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 125000004432 carbon atoms Chemical group C* 0.000 claims 1
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 241000238631 Hexapoda Species 0.000 description 3
- 230000000875 corresponding Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- NZZIMKJIVMHWJC-UHFFFAOYSA-N Dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 description 2
- -1 Ethylacetyl Chemical group 0.000 description 2
- 125000002587 enol group Chemical group 0.000 description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000000241 respiratory Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JRMAQQQTXDJDNC-UHFFFAOYSA-M 2-ethoxy-2-oxoacetate Chemical compound CCOC(=O)C([O-])=O JRMAQQQTXDJDNC-UHFFFAOYSA-M 0.000 description 1
- YRKCREAYFQTBPV-UHFFFAOYSA-N Acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 1
- SESFRYSPDFLNCH-UHFFFAOYSA-N Benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 210000000056 organs Anatomy 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
Classifications
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
DEUTSCHES REICHGERMAN EMPIRE
AUSGEGEBEN AW
16. AUGUST 1941ISSUED AW
AUGUST 16, 1941
REICHSPATENTAMTREICH PATENT OFFICE
PATENTSCHRIFTPATENT LETTERING
M 709435 KLASSE 451 GRUPPE 3oi M 709435 CLASS 451 GROUP 3oi
U 14198 IVaJ45lU 14198 IVaJ45l
ist als Erfinder genannt worden.has been named as the inventor.
Kilgore Development Corporation in Washington InsektentötungsmittelKilgore Development Corporation in Washington Insecticides
Patentiert im Deutschen Reich vom 8. Februar 1938 an Patenterteilung bekanntgemacht am 10. Juli 1941 ·Patented in the German Reich on February 8, 1938 Patent granted on July 10, 1941
Die Erfindung bezieht sich auf die Herstellung von insektentötenden Mitteln und besteht in Lösungen oder Suspensionen, welche besonders wirksame Stoffe enthalten. Diese wirksamen Stoffe bestehen erfindungsgemäß aus Verbindungen, welche eine Methylengruppe zwischen zwei Ketogruppen enthalten. Es handelt sich also um Verbindungen, welche an der Methylengruppe bewegliche Wasserstoffatome enthalten. Diese Verbindungen existieren bekanntlich ■ in zwei tautormeren Formen: der Ketoform und der Enolform. Erfindungsgemäß kommen vor allem folgende Vertreter in Frage:The invention relates to the manufacture of insecticides and consists in solutions or suspensions which contain particularly effective substances. These According to the invention, active substances consist of compounds which have a methylene group contained between two keto groups. So it is a matter of connections, which mobile hydrogen atoms on the methylene group contain. As is well known, these compounds exist in two more authoritative forms Forms: the keto form and the enol form. According to the invention, the following are especially important Representative in question:
•5 . i. AcetylacetonCH3COCH2COCH3,• 5. i. Acetylacetone CH 3 COCH 2 COCH 3 ,
2. Dibenzoylmethan C6H5COCH2COC6H5,2. Dibenzoylmethane C 6 H 5 COCH 2 COC 6 H 5 ,
3. Benzoylaoeton CeH5(COCH2COCH3,3. Benzoylaoeton CeH 5 (COCH 2 COCH 3 ,
4. Äthylacetylbrenztraubenester4. Ethylacetyl pyruve ester
ao CH3COCH2COCOOc2H5, ao CH 3 COCH 2 COCOOc 2 H 5 ,
5. Äthylbenzoylbrenztraubenester5. Ethylbenzoyl pyruve ester
C0H5COCH2COCOOc2H5.C 0 H 5 COCH 2 COCOOc 2 H 5 .
Die Verbindungen entsprechend den Vertretern ι, 2 und 3 können in bekannter Weise nach der Claisenkondensation vermittels metallischen Natriums hergestellt werden. Die Verbindungen entsprechend den Vertretern 4 und 5 können in ähnlicher Weise unter Verwendung von. zweibasischen Estern, wie z.B. Äthyloxalat, hergestellt werden. In den genannten Verbindungen können die am Anfang stehenden Methyl- oder Phenylgruppen sowie die am Ende hinter der letzten Ketogruppe bzw. hinter der Carboxylgruppe stehen- den Methyl- oder Äthylgruppen durch andere aliphatische, aromatische bzw. aliphatischaromatische Gruppen ersetzt werden.The compounds corresponding to the representatives ι, 2 and 3 can in a known manner after the Clais condensation by means of metallic sodium. the Compounds corresponding to Representatives 4 and 5 can be used in a similar manner from. dibasic esters such as ethyl oxalate. In the mentioned Compounds can be the methyl or phenyl groups at the beginning as well as those at the end behind the last keto group or behind the carboxyl group- the methyl or ethyl groups by other aliphatic, aromatic or aliphatic-aromatic Groups are replaced.
Die beweglichen Wasserstoffatome der erfindungsgemäß zu vierwendenden Produkte wirken anscheinend derart, daß die Verbindungen in der Enolform besonders Sauerstoff aufnehmen. Gelangen also diese Stoffe in die Atmungsorgane von Insekten, so findet· eine Lahmlegung der Atmungsvorgänge und somit eine wirksame Tötung der Insekten statt.The mobile hydrogen atoms of the products to be used according to the invention apparently act in such a way that the compounds in the enol form particularly oxygen take up. If these substances get into the respiratory organs of insects, then one finds Paralysis of the respiratory processes and thus an effective killing of the insects takes place.
Des weiteren wurde gefunden, daß man mit Vorteil' speziell gammasubstitüierte ,Alpha-, Gammadiketocarbonsäureester verwendet, wo-, bei aliphatische oder fettaromatische Gruppen^· in Gämmastellung sich befinden und wobpiS diese Substituenten mehr als ein Kohlenstdfe- ; atom enthalten sollen. Als solche kommen Jits'; Betracht Verbindungen von der allgemeinen Formel RCOCh2COCOOR', wobei R z.B.It has also been found that it is advantageous to use specifically gamma-substituted, alpha, gammadiketocarboxylic acid esters, where aliphatic or fatty aromatic groups are in the gummy position and these substituents have more than one carbon; atom should contain. As such come jits'; Consider compounds of the general formula RCOCh 2 COCOOR ', where R is for example
ίο Isobutylgruppen und R' einen beliebigen aliphatischen oder fettaromatischen Rest darstellen. ίο isobutyl groups and R 'any aliphatic or represent a fatty aromatic residue.
Als weitere Beispiele seien hier insonderheit genannt: a-^-Diketoisokaprylsäuremethylester, -äthylester, -butylester, -isopropylester sowie die entsprechenden Cyclohexylester, Benzylester, Amylester und Allylester. Des weiteren kommen in Betracht beliebige Ester der α-γ-D'iketokapronsäure, a-^-Diketolsokaprylsäure, Die genannten Verbindungen können in beliebiger Weise entweder als solche oder gelöst bzw. suspendiert in geeigneten Flüssigkeiten, wie z. B. Ligroin, zur Anwendung gelangen. Dabei können diese Flüssigkeiten z.B. durch Zerstäuben zur Anwendung gebracht werden. Die vorgeschlagenen Ester haben weiterden Vorteil, daß sie hochsiedend, nichtflüchtig sind und zudem noch andere erwünschte physikalische Eigenschaften, wie geringen Geruch, besitzen.As further examples are mentioned here in particular: a - ^ - Diketoisokaprylsäuremethylester, -äthylester, -butylester, -isopropylester as well as the corresponding cyclohexylester, benzylester, amylester and allylester. Any esters of α-γ- d'iketokaproic acid, a - ^ - diketolsocaprylic acid can also be used. B. ligroin, are used. These liquids can be used, for example, by atomization. The proposed esters also have the advantage that they are high-boiling, non-volatile and also have other desirable physical properties, such as low odor.
Es wurden 12 ecm einer 5 0/0igen Lösung Dibenzoylmethan in Kerosen mit Benzol i^ijs,: Hilfslösungsmittel hergestellt. Das! Lö-&äi|iigsmittel, Kerosen mit Benzol, ist an sich Njnwirksam gegen Insekten. Für den Versuch wurden ungefähr 100 gewöhnliche Hausfliegen, muscä domestica, in eine geschlossene Kammer gebracht und das Tötungsmittel in diese Kammer hineingestäubt. 24 Stunden .danach waren 37% der Fliegen getötet.12 ecm of a 50/0 solution of dibenzoylmethane in kerosene were prepared with benzene i ^ ijs,: auxiliary solvents. That ! Solvents, kerosene with benzene, are in themselves not effective against insects. For the experiment, about 100 common house flies, musca domestica, were placed in a closed chamber and the killing agent was dusted into this chamber. 24 hours after that, 37% of the flies were killed.
Claims (3)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE709435C true DE709435C (en) |
Family
ID=577098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT709435D Active DE709435C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE709435C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3760087A (en) * | 1970-01-19 | 1973-09-18 | Hoffmann La Roche | Perfume compositions containing ethyl 2,4-dioxohexanoate |
-
0
- DE DENDAT709435D patent/DE709435C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3760087A (en) * | 1970-01-19 | 1973-09-18 | Hoffmann La Roche | Perfume compositions containing ethyl 2,4-dioxohexanoate |
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