DE1058306B - Pest repellants - Google Patents
Pest repellantsInfo
- Publication number
- DE1058306B DE1058306B DEB46837A DEB0046837A DE1058306B DE 1058306 B DE1058306 B DE 1058306B DE B46837 A DEB46837 A DE B46837A DE B0046837 A DEB0046837 A DE B0046837A DE 1058306 B DE1058306 B DE 1058306B
- Authority
- DE
- Germany
- Prior art keywords
- methylenedioxy
- propyl
- nitrobenzene
- allethrin
- compounds
- 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.)
- Pending
Links
- 241000607479 Yersinia pestis Species 0.000 title 1
- SYSWOELRQPHJBC-UHFFFAOYSA-N 5-nitro-6-propyl-1,3-benzodioxole Chemical compound C1=C([N+]([O-])=O)C(CCC)=CC2=C1OCO2 SYSWOELRQPHJBC-UHFFFAOYSA-N 0.000 claims description 6
- 150000002828 nitro derivatives Chemical class 0.000 claims description 6
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 4
- ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 claims description 3
- 239000000575 pesticide Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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 group [H]* 0.000 claims description 2
- 230000000749 insecticidal effect Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 7
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 7
- 229940024113 allethrin Drugs 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 4
- 229960005235 piperonyl butoxide Drugs 0.000 description 4
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 description 3
- -1 methylenedioxy compounds Chemical class 0.000 description 3
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 3
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- SNWQAKNKGGOVMO-UHFFFAOYSA-N 5-nitro-1,3-benzodioxole Chemical compound [O-][N+](=O)C1=CC=C2OCOC2=C1 SNWQAKNKGGOVMO-UHFFFAOYSA-N 0.000 description 1
- NRZWECORTTWSEF-UHFFFAOYSA-N 6-nitro-1,3-benzodioxole-5-carbaldehyde Chemical compound C1=C(C=O)C([N+](=O)[O-])=CC2=C1OCO2 NRZWECORTTWSEF-UHFFFAOYSA-N 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 241000254179 Sitophilus granarius Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
- A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Schädlingsbekämpfungsmittel Es sind verschiedene Abkömmlinge des Methylendioxybenzols als Synergisten für insektizide Verbindungen der Pyrethrumklasse bekannt. Insbesondere hat sich das Piperonylbutoxyd genannte 1-(2'-n-Propyl-4',5'-methylendioxyphenyl)-2,5,8-trioxadodekan für diese Zwecke bewährt.Pesticides There are various derivatives of methylenedioxybenzene known as synergists for insecticidal compounds of the pyrethrum class. In particular 1- (2'-n-propyl-4 ', 5'-methylenedioxyphenyl) -2,5,8-trioxadodecane, called piperonyl butoxide proven for these purposes.
Es wurde nun gefunden, daß Nitroverbindungen des Methylendioxybenzols der allgemeinen Formel in der R Wasserstoff oder einen Alkyl-, Alkenyl-, Carbonyl-, Carboxyl- oder Carbalkoxyrest bedeutet, eine ausgezeichnete synergistische Wirksamkeit gegenüber Verbindungen der Pyrethrumklasse entfalten. Derartige Nitroverbindungen des Methylendioxybenzols sind z. B. 1,2-Methylendioxy-4-nitrobenzol, 1-n-Propyl-3,4-methylendioxy-6-nitrobenzol, 1-Propenyl- oder 1-Allyl-3,4-methylendioxy-6-nitro-benzol, 6-Nitropiperonal und 6-Nitropiperonylsäure.It has now been found that nitro compounds of methylenedioxybenzene of the general formula in which R is hydrogen or an alkyl, alkenyl, carbonyl, carboxyl or carbalkoxy radical, display excellent synergistic activity against compounds of the pyrethrum class. Such nitro compounds of methylenedioxybenzene are z. B. 1,2-methylenedioxy-4-nitrobenzene, 1-n-propyl-3,4-methylenedioxy-6-nitrobenzene, 1-propenyl- or 1-allyl-3,4-methylenedioxy-6-nitro-benzene, 6 -Nitropiperonal and 6-nitropiperonyl acid.
Im Vergleich mit den bekannten Synergisten ist die Herstellung dieser Nitroverbindungen besonders wirtschaftlich, weil sie aus leicht zugänglichen Methylendioxyverbindungen durch Nitrierung in einfacher Weise nach bekannten Methoden darstellbar sind. Ein besonderer Vorteil dieser Nitroverbindungen ist die überraschend geringe Toxizität gegenüber Warmblütlern und außerdem ihre gute Beständigkeit gegen Licht- und Lufteinwirkung im Vergleich mit den bisher für die vorliegenden Zwecke benutzten, leicht oxydablen Methylendioxyverbindungen. Gegenüber dem bekannten Propionyl-dioxymethylenpropylbenzol haben die erfindungsgemäß zuverwendenden Nitroverbindungen eine bessere synergistische Wirkung. Beispiel 1 Auf Glasplatten von 8 - 8 cm, die mit den acetonischen Lösungen der weiter unten angegebenen Wirkstoffe behandelt wurden, werden nach Verdunsten des Lösungsmittels für 10 Minuten Kornkäfer gebracht. Darauf werden die Käfer in saubere Beobachtungsgefäße übergeführt und die Mortalität in 24 Stunden bestimmt.In comparison with the known synergists, the production of this one Nitro compounds are particularly economical because they are made from easily accessible methylenedioxy compounds can be prepared in a simple manner by known methods by nitration. A A particular advantage of these nitro compounds is their surprisingly low toxicity to warm-blooded animals and also their good resistance to light and air in comparison with the easily oxidizable ones previously used for the present purposes Methylenedioxy compounds. Compared to the well-known propionyl-dioxymethylene-propylbenzene the nitro compounds to be used according to the invention have a better synergistic one Effect. Example 1 On glass plates of 8 - 8 cm, which contain the acetone solutions The active ingredients listed below are treated after evaporation of the solvent brought grain weevils for 10 minutes. Thereupon the beetles are in Transferring clean observation vessels and determining the mortality in 24 hours.
0,5 mg Pyrethrin.................. unwirksam 0,5 mg Pyrethrin -f-
5 mg Piperonylbutoxyd = 1-(2'-n-Propyl-4',5'-methylendioxyphenyl) -2,5,8-trioxadodekan
. . . . . . . . . . . . . . . . . . . . . . . . . 1001)ioige Abtötung 0,5 mg Pyrethrin
+ 5 mg 1-n-Propyl-3,4-methylendioxy-6-nitrobenzol . . 99°/oige Abtötung Beispiel
2 Glasgefäße von 250 cm3 Inhalt werden mit 1 ccm acetonischer Lösungen der weiter
unten angegebenen Wirkstoffe behandelt. Nach Verdunsten des Lösungsmittels werden
4 Tage alte Stubenfliegen in die Gefäße eingesetzt. Die Bestimmung der Mortalität
erfolgt nach 2 Stunden.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB46837A DE1058306B (en) | 1957-11-19 | 1957-11-19 | Pest repellants |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB46837A DE1058306B (en) | 1957-11-19 | 1957-11-19 | Pest repellants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1058306B true DE1058306B (en) | 1959-05-27 |
Family
ID=6968055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB46837A Pending DE1058306B (en) | 1957-11-19 | 1957-11-19 | Pest repellants |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1058306B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019175713A1 (en) * | 2018-03-14 | 2019-09-19 | Basf Corporation | New catechol molecules and their use as inhibitors to p450 related metabolic pathways |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE856973C (en) * | 1949-04-22 | 1952-11-24 | Rex Res Corp | Process for the manufacture of insecticides |
| DE913716C (en) * | 1946-04-01 | 1954-06-18 | Nat Distillers Products Corp | Pest repellants |
| DE948653C (en) * | 1954-11-27 | 1956-09-06 | Riedel De Haeen Ag | Pest repellants |
| DE953878C (en) * | 1955-05-12 | 1956-12-06 | Basf Ag | Process for the preparation of insecticidal derivatives of tetrahydrofuran |
-
1957
- 1957-11-19 DE DEB46837A patent/DE1058306B/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE913716C (en) * | 1946-04-01 | 1954-06-18 | Nat Distillers Products Corp | Pest repellants |
| DE856973C (en) * | 1949-04-22 | 1952-11-24 | Rex Res Corp | Process for the manufacture of insecticides |
| DE948653C (en) * | 1954-11-27 | 1956-09-06 | Riedel De Haeen Ag | Pest repellants |
| DE953878C (en) * | 1955-05-12 | 1956-12-06 | Basf Ag | Process for the preparation of insecticidal derivatives of tetrahydrofuran |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019175713A1 (en) * | 2018-03-14 | 2019-09-19 | Basf Corporation | New catechol molecules and their use as inhibitors to p450 related metabolic pathways |
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