US2103195A - Insecticide - Google Patents
Insecticide Download PDFInfo
- Publication number
- US2103195A US2103195A US151915A US15191537A US2103195A US 2103195 A US2103195 A US 2103195A US 151915 A US151915 A US 151915A US 15191537 A US15191537 A US 15191537A US 2103195 A US2103195 A US 2103195A
- Authority
- US
- United States
- Prior art keywords
- rotenone
- compound
- acid
- dichloroacetic acid
- water
- 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 - Lifetime
Links
- 239000002917 insecticide Substances 0.000 title description 3
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 42
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 34
- 229940080817 rotenone Drugs 0.000 description 32
- 150000001875 compounds Chemical class 0.000 description 28
- 229960005215 dichloroacetic acid Drugs 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000284 extract Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000003513 alkali Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 241000913832 Deguelia Species 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001294739 Cracca Species 0.000 description 2
- 241000522187 Derris Species 0.000 description 2
- 241000219997 Lonchocarpus Species 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- JUVIOZPCNVVQFO-HBGVWJBISA-N rotenone Chemical compound O([C@H](CC1=C2O3)C(C)=C)C1=CC=C2C(=O)[C@@H]1[C@H]3COC2=C1C=C(OC)C(OC)=C2 JUVIOZPCNVVQFO-HBGVWJBISA-N 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical group CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 description 1
- 241000213914 Tephrosia <angiosperm> Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 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
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Definitions
- My invention relates to a heretofore unknown compound made from a chemical combination of rotenone and dichloroacetic acid.
- the object of my invention is to produce this new compound which has valuable properties as an insecticide, and is of considerable importance in the development of new and shortened methods for the analysis of materials containing rotenone.
- My invention is a new chemical compound and contains 75.35 per cent by weight of rotenone and 24.65 per cent by weight of dichloroacetic acid.
- the empirical formula of this new com- 5 pound is therefore C23H220aC2I-I202CI2.
- This new compound would be classified in the art as an addition compound, and may also be referred to as a solvate.
- This new compound differs markedly from all other known addition com- 30 pounds, or solvates, of rotenone in that it is a compound of rotenone and a strong, or highly ionized, acid.
- dichloroacetic acid is far superior to other fatty acids and chlorinated fatty acids in solvent power for V rotenone is particularly important from the standpoint of ease of preparation of the new compound.
- the compound of my invention may be prepared in several ways. It may be produced from rotenone by dissolving said rotenone in dichloroacetic acid, heating the solution and adding water to obtain a crystalline product therefrom, said product being my invention.
- This addition compound of rotenone and dichloroacetic acid is also produced from extracts of the roots of plants of the genus Derrz's deguelia, extracts of the roots of plants of the genus Lonchocarpus, extracts of the roots of plants of the genus Tephrosia 'cracca, or from extracts of any other plant material containing rotenone. This is accomplished by dissolving any 40 of the above mentioned extracts in dichloroacetic acid, heating the solution, adding a. suitable quantity of hot water and allowing the whole to cool. The material which crystallizes out is substantially the product covered by my invention.
- the preferred method for the purification of the product thus obtained is to dissolve it in hot dichloroacetic acid, add a suitable quantity of hot water, allow the whole to cool, and separate the material, which crystallizes out, by filtration or other similar means employed to separate substances.
- Example I 2 grams of rotenone is dissolved in a mixture of 20 cc. of dlchloroacetic acid and 5 cc. of water. The solution is warmed to a temperature of 50 C. and 150 cc. of water at the same temperature added slowly with continuous stirring, when crystallization occurs. This mix ture is cooled to 20 C. and'the crystalli'n'e compound filtered off and washed with water at 20 C. until all excess dichloroacetic acid is removed.
- the crystalline product is dried to constantweight in a current of air at 40 C.
- the product so obtained is the pure addition compound of rotenone and dichloroacetic acid, which is the product covered by this invention.
- Example II grams of the extract from the roots of Derris deguelia sp. is dissolved in a mix"- ture of 25 cc. of dichloroacetic acid and 5 cc. of water. The solution is heated to a temperature ofe50 C. and '70 cc. of water at the same temperature added slowly with continuous stirring; This mixture is cooled to C. and the separated material filtered off, washed with water at 20 C. until all excess dichloroacetic acid is removed, and dried'to constant Weight at 40 C. The product so obtained is substantially the addition compound'of rotenone and dichloroacetic 2. A new chemical combination ,of rotenone and dichloroacetic acid having the empirical formula C23H220e.C2H202C12.
- a process formaking a chemical compound of" rotenone and dichloroacetic acid which comprises essentially dissolving" rot'endri'e iri' dichloroacetic acid, adding water and Separating the resulting crystalline product.
- a process for making a chemical compound of rotenone and dichloroacetic acid which comprises essentially dissolving an extract of the roots of plants of the genus Derris deguelia, in dichloroacetic acid, adding water and separating the resulting crystalline product.
- a -process for making a chemical compound of rotenone and dichloroacetic acid which comprises essentially dissolving an extract of the rootsofplants of the genus Lonchocarpus in dichloroacetic'acid, adding water and separating the resulting crystalline product.
- a process for making a chemical compound of rotenone anddichloroacetic acid which comprises essentially dissolving an extract of the roots ofplants of the genus Tcphrosz'a cracca in dichloroacetic acid, adding'water and separatin 1 the resulting crystalline product; 7; A-processyfor makinga chemical compound of rotenone'and dichloroaceticaizid; which com-
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- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Agronomy & Crop Science (AREA)
- Mycology (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Dec. 21, 1937 UNITED STATES INSECTICIDE Howard A. Jones, Washington, D. 0., dedicated to the free use of the People of the United States of America No Drawing. Application July 3, 1937,
Serial No. 151,915
8 Claims. (01. 2c0 54) (Granted under the act of March 3, 1883, as
amended April 30, 1928; 370 0. G. 757) r This application is made under the act of March 3, 1883, as amended by the act of April 30, 1928, and the invention herein described, and claimed, if patented, may be manufactured and 5 used by or for the Government of the United States for governmental purposes without the payment to me of any royalty thereon.
I hereby dedicate the invention herein described to the free use of the People of the 10 United States of America to take effect on the granting of a patent to me.
My invention relates to a heretofore unknown compound made from a chemical combination of rotenone and dichloroacetic acid.
15 The object of my invention is to produce this new compound which has valuable properties as an insecticide, and is of considerable importance in the development of new and shortened methods for the analysis of materials containing rotenone.
My invention is a new chemical compound and contains 75.35 per cent by weight of rotenone and 24.65 per cent by weight of dichloroacetic acid. The empirical formula of this new com- 5 pound is therefore C23H220aC2I-I202CI2. This new compound would be classified in the art as an addition compound, and may also be referred to as a solvate. This new compound differs markedly from all other known addition com- 30 pounds, or solvates, of rotenone in that it is a compound of rotenone and a strong, or highly ionized, acid.
I have prepared this new chemical compound and have found that it possesses distinctly different physical and chemical properties from those of both rotenone and dichloroacetic acid. The compound crystallizes in colorless, lath-like crystals,- while rotenone crystalizes in flat, hexagonal-shaped plates. This compound also dif- 40 fers chemically from rotenone in that it possesses an acidic group which may be titrated with alkali by dissolving the compound in a waterimmiscible solvent such as chloroform and shaking this solution with water while adding 45 the alkali. Because of this fact the compound is useful in the development of shorter analytical procedures for the determination of rotenone. Rotenone itself does not possess any such acidic group and cannot be titrated with alkali in this 50 way.
The inventor has already reported in the literature an addition compound of rotenone and acetic acid in which the molecular ratio is two mols of rotenone to one of acetic acid. I have 55 also found that other fatty acids and chlorinated fatty acids combine with rotenone in this mol. ratio. Thus propionic acid and alpha-chloropropionic acid form compounds in which the molecular ratio is two mols of rotenone to one of acid. However, the present compound of ro- 5 tenone and dichloroacetic acid is entire-1y different from these in the fact-that it is the only one which has thus far been found in which rotenone combines With an acid in a moi. ratio of one to one. This is particularly advantageous in the application of this compound to use in analytical procedures in that a much larger titer of alkali is obtained than with other compounds in which rotenone combines with acids,
and the resulting methods are correspondingly more accurate. The fact that dichloroacetic acid is far superior to other fatty acids and chlorinated fatty acids in solvent power for V rotenone is particularly important from the standpoint of ease of preparation of the new compound.
Furthermore the fusion of rotenone and dichloroacetic acid has resulted in a product possessing insecticidal properties different from those possessed by rotenone acting alone, and dichlog5 roacetic acid acting alone.
The compound of my invention may be prepared in several ways. It may be produced from rotenone by dissolving said rotenone in dichloroacetic acid, heating the solution and adding water to obtain a crystalline product therefrom, said product being my invention.
This addition compound of rotenone and dichloroacetic acid is also produced from extracts of the roots of plants of the genus Derrz's deguelia, extracts of the roots of plants of the genus Lonchocarpus, extracts of the roots of plants of the genus Tephrosia 'cracca, or from extracts of any other plant material containing rotenone. This is accomplished by dissolving any 40 of the above mentioned extracts in dichloroacetic acid, heating the solution, adding a. suitable quantity of hot water and allowing the whole to cool. The material which crystallizes out is substantially the product covered by my invention. The preferred method for the purification of the product thus obtained is to dissolve it in hot dichloroacetic acid, add a suitable quantity of hot water, allow the whole to cool, and separate the material, which crystallizes out, by filtration or other similar means employed to separate substances.
The methods of producing my compound are illustrated by the following examples:
Example I.2 grams of rotenone is dissolved in a mixture of 20 cc. of dlchloroacetic acid and 5 cc. of water. The solution is warmed to a temperature of 50 C. and 150 cc. of water at the same temperature added slowly with continuous stirring, when crystallization occurs. This mix ture is cooled to 20 C. and'the crystalli'n'e compound filtered off and washed with water at 20 C. until all excess dichloroacetic acid is removed.
The crystalline product is dried to constantweight in a current of air at 40 C. The product so obtained is the pure addition compound of rotenone and dichloroacetic acid, which is the product covered by this invention.
Example II grams of the extract from the roots of Derris deguelia sp. is dissolved in a mix"- ture of 25 cc. of dichloroacetic acid and 5 cc. of water. The solution is heated to a temperature ofe50 C. and '70 cc. of water at the same temperature added slowly with continuous stirring; This mixture is cooled to C. and the separated material filtered off, washed with water at 20 C. until all excess dichloroacetic acid is removed, and dried'to constant Weight at 40 C. The product so obtained is substantially the addition compound'of rotenone and dichloroacetic 2. A new chemical combination ,of rotenone and dichloroacetic acid having the empirical formula C23H220e.C2H202C12.
3. A process formaking a chemical compound of" rotenone and dichloroacetic acid, which comprises essentially dissolving" rot'endri'e iri' dichloroacetic acid, adding water and Separating the resulting crystalline product.
41 A process for making a chemical compound of rotenone and dichloroacetic acid, which comprises essentially dissolving an extract of the roots of plants of the genus Derris deguelia, in dichloroacetic acid, adding water and separating the resulting crystalline product.
5; A -process for making a chemical compound of rotenone and dichloroacetic acid, which comprises essentially dissolving an extract of the rootsofplants of the genus Lonchocarpus in dichloroacetic'acid, adding water and separating the resulting crystalline product.
6. A process for making a chemical compound of rotenone anddichloroacetic acid, which comprises essentially dissolving an extract of the roots ofplants of the genus Tcphrosz'a cracca in dichloroacetic acid, adding'water and separatin 1 the resulting crystalline product; 7; A-processyfor makinga chemical compound of rotenone'and dichloroaceticaizid; which com-
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US151915A US2103195A (en) | 1937-07-03 | 1937-07-03 | Insecticide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US151915A US2103195A (en) | 1937-07-03 | 1937-07-03 | Insecticide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2103195A true US2103195A (en) | 1937-12-21 |
Family
ID=22540787
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US151915A Expired - Lifetime US2103195A (en) | 1937-07-03 | 1937-07-03 | Insecticide |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2103195A (en) |
-
1937
- 1937-07-03 US US151915A patent/US2103195A/en not_active Expired - Lifetime
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