USRE22700E - Paul mtjller - Google Patents
Paul mtjller Download PDFInfo
- Publication number
- USRE22700E USRE22700E US22700DE USRE22700E US RE22700 E USRE22700 E US RE22700E US 22700D E US22700D E US 22700DE US RE22700 E USRE22700 E US RE22700E
- Authority
- US
- United States
- Prior art keywords
- paul
- mtjller
- compounds
- line
- insecticide
- 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
- 150000001875 compounds Chemical class 0.000 description 11
- 230000000749 insecticidal Effects 0.000 description 6
- 239000002917 insecticide Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 241001124076 Aphididae Species 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- JUVIOZPCNVVQFO-HBGVWJBISA-N Rotenone Natural products 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HFFLGKNGCAIQMO-UHFFFAOYSA-N Chloral Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- 229960002327 Chloral Hydrate Drugs 0.000 description 1
- RNFNDJAIBTYOQL-UHFFFAOYSA-N Chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N Diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 210000004400 Mucous Membrane Anatomy 0.000 description 1
- SNICXCGAKADSCV-JTQLQIEISA-N Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- 229960002715 Nicotine Drugs 0.000 description 1
- 210000001331 Nose Anatomy 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 210000003800 Pharynx Anatomy 0.000 description 1
- 229940080817 Rotenone Drugs 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 230000000844 anti-bacterial Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- XDLDASNSMGOEMX-UHFFFAOYSA-N benzene benzene Chemical compound C1=CC=CC=C1.C1=CC=CC=C1 XDLDASNSMGOEMX-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 229930015196 nicotine Natural products 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
Definitions
- This invention relates to insecticides. For combatting insects of all kind such as flies.
- sonous character also used for the protection of plants, but it cannot be used in inhabited rooms.
- Both the first mentioned agents show the disadvantage of smelling disagreeably in -spite of the admixture of strong perfuming agent. when they are used in form of petroleum solutions.
- heating takes place after some time. which first increases up to about 60 C. and then slowly decreases again. Stirring is continued until the reaction mass has cooled down to room temperature and contains solid particles. Then it.is poured into much water whereby the 'raw condensation product separates out in a solid term. It is well washed out and. after being recrystallised from alcohol, it is obtained in form of white. line crystals which show a weakly fruitas these halogenated not exert even in finely dispersed form any'irritating eilect on the mucous membranes ofthe eyes. nose'or throat.
- the said compounds correspond to the followins general formula wherein X represents chlorine atoms and! and 2 mean certain aromatic radicals of the benzene se es.
- the said compounds can be used as powder or, when dissolved or emulsified, in solvents or diluents. but they can also be used together with other inert substances inactive by themselves or in combination with' insecticide agents.
- OJHIOI and'an insectieiw carrier selected from the group consisting'o: powder, solvent free from,
- a contact insecticide comprising a solution 0! the chemical compound .-di(p-chlorophenyl)-p,p,p-trlchlorethane in a. petroleum solvent.
- a contact insecticide comprising the chemical compound .-di(p-ch1orophenyl) -fi.B-fl-trichlorethane and a carrier therefor consisting of an aqueous emulsion.
- a contact insecticide comprising a solution of the chemical compound modu o-chlorophenyli-pfip-trichlorethane in a. solvent tree from ether.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Reicsued Dec. 4, 1945 UNITED STATES PATENT OFFICE DEVITALIZING COMPOSITION OF MATTER Paul Miilier, Basel, Switaerland, assirncr to the iirm J. B. Geiry A. G., Basel. Switzerland No Drawing. Orisinal No. 2,329,074.
1943, Serial No. 881,768, March 4.
tember l, 1941. Serial No. 005-431 Application for dated Seprel'ssue July 16, 1945,
5 Claims. (0!. 167-30) This invention relates to insecticides. For combatting insects of all kind such as flies.
' stinging flies, moths. beetles. plant-lice and so on.
there are mostly used petroleum solutions of pyrethrine or rotenone or aqueous emulsions of such compounds. Nicotine is. in spite of its .poi-
sonous character, also used for the protection of plants, but it cannot be used in inhabited rooms. Both the first mentioned agents show the disadvantage of smelling disagreeably in -spite of the admixture of strong perfuming agent. when they are used in form of petroleum solutions. In
Therefore, it is very surprising that-the con-- densation products of 1 molecule of choral with.
2 molecules of certain compounds with replaceable hydrogen from the benzene series.,show, beside the sure killing eifect on insects, only a very weak and not at all disagreeable odor and do The following example illustrates the present invention. The parts are by weight, unless otherwise stated.
Example .By treatinmwhile strongly stirring, a mixture of z'molecules of benzene or chlorobenzene with one molecule of chloral or chloralhydrate with an excess of concentrated sulfuric acid (of 100.
per cent strength) heating takes place after some time. which first increases up to about 60 C. and then slowly decreases again. Stirring is continued until the reaction mass has cooled down to room temperature and contains solid particles. Then it.is poured into much water whereby the 'raw condensation product separates out in a solid term. It is well washed out and. after being recrystallised from alcohol, it is obtained in form of white. line crystals which show a weakly fruitas these halogenated not exert even in finely dispersed form any'irritating eilect on the mucous membranes ofthe eyes. nose'or throat.
The said compounds correspond to the followins general formula wherein X represents chlorine atoms and! and 2 mean certain aromatic radicals of the benzene se es.
The said compounds can be used as powder or, when dissolved or emulsified, in solvents or diluents. but they can also be used together with other inert substances inactive by themselves or in combination with' insecticide agents.
They are very stable in neutral'or well as in acid or weakly alkaline solutions and their preparation is technically very simple.
The preparation of the described compounds is known (0. Zeidler. 13.7. i181).
ilmsicide. bactericide or odor. The formulas of 'these compounds are the following ones:
h The first compound melts at 64 6.. the second one at 103-105 0. (about the preparation see also 0. Fischer. 8.7. 1191). These two diphenylmethane compounds react surely against files, by spraying 5 com. of an alcoholic solution of 5 per cent strength per cubic metre of room. Death takes place, for files, within 2 hours: already after 10-15 minutes nearly all flies are so paralyzed that they can no longer fly. Moths. plant-lice or other pests are also destroyed within a very short 'time'by the sprayed compounds. Instead of solutions in alcohol. petroleum or similar solvents one may; in many cases. also use aqueous emulsions. Their efllciency does not thereby decrease even on lcn storage, which is the case-for many known insecticide preparations.
What I claim is: l. (in insecticidal composition of matter comprising the combination of the active ingredient c.e-di (p-chiorophenyl) -p.p.p-trichlorethane of the formula cimci etc-4m:
OJHIOI and'an insectieiw carrier selected from the group consisting'o: powder, solvent free from,
ether. and aqueous emulsion.
therefor.
3. A contact insecticide comprising a solution 0! the chemical compound .-di(p-chlorophenyl)-p,p,p-trlchlorethane in a. petroleum solvent.
4. A contact insecticide comprising the chemical compound .-di(p-ch1orophenyl) -fi.B-fl-trichlorethane and a carrier therefor consisting of an aqueous emulsion.
5. A contact insecticide comprising a solution of the chemical compound modu o-chlorophenyli-pfip-trichlorethane in a. solvent tree from ether.
PAUL mm.
CERTIFICATE OF CORRECTION.
Reissue No. 22,700. December 1;, 191 5,
PAUL HELLER.
It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows: Page 1, first column, line 51, after "all" insert --e--; line 51, for "or well" read --ae well--; and second column, line 25, between the formulae insert the word "and"; line 55, for "insecticidal" read --ineecticide--; and that the said Letters Patent should be read with this correction therein that the some may conform to the record of the case in the Patent Office.
Signed and sealed this 18th day of December, A. D. 1915.
Leslie Frazer (Seal) First Assistant Cmnmieeioner of-Patents.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| USRE22700E true USRE22700E (en) | 1945-12-04 |
Family
ID=2089454
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US22700D Expired USRE22700E (en) | Paul mtjller |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | USRE22700E (en) |
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2430586A (en) * | 1945-07-26 | 1947-11-11 | Sherwin Williams Co | Dihalophenyl alkyl carbinol pesticides |
| US2442653A (en) * | 1946-12-10 | 1948-06-01 | Us Rubber Co | Insecticides |
| US2442652A (en) * | 1945-06-19 | 1948-06-01 | Us Rubber Co | Insecticides |
| US2442760A (en) * | 1945-07-09 | 1948-06-08 | Dow Chemical Co | Dichlorodiphenyltrichloroethane and cyclohexyldiphenylether insecticidal composition |
| US2448405A (en) * | 1945-06-23 | 1948-08-31 | Allied Chem & Dye Corp | Xanthone-ddt insecticide |
| US2448665A (en) * | 1945-06-22 | 1948-09-07 | Elmer E Fleck | Low-temperature noncrystallizing ddt-alkylated naphthalene insecticide |
| US2452759A (en) * | 1944-09-22 | 1948-11-02 | Velsicol Corp | Insecticide containing methylated naphthalene and 4,4' dichloro-di-phenyl-trichloroethane |
| US2460377A (en) * | 1945-10-02 | 1949-02-01 | Celanese Corp | Filaments of plasticized lower fatty acid esters of cellulose |
| US2490958A (en) * | 1945-05-15 | 1949-12-13 | Ciba Ltd | Pest-combating compositions and spraying liquids of enhanced adhering capacity |
| US2491632A (en) * | 1944-09-09 | 1949-12-20 | Stauffer Chemical Co | Methods of producing insecticidal compositions containing relatively small quantities of 2,2-bis(p-chlorophenyl) - 1,1,1 - trichlorethane |
| US2510870A (en) * | 1946-05-09 | 1950-06-06 | Dow Chemical Co | Insecticidal composition comprising 1.1-di-(4-chlorophenyl)-2.2.2-trichloro-ethane and 1.1-di-(monochloro-phenyl)-ethane |
| US2515803A (en) * | 1945-05-17 | 1950-07-18 | Segessemann Ernest | Sulfonated 1, 1, 1-trichloro-2,2-bis (p-chlorophenyl) ethane |
| US2520551A (en) * | 1945-04-27 | 1950-08-29 | Lowell B Kilgore | N-substituted oxyacetamides |
| US2524590A (en) * | 1946-04-22 | 1950-10-03 | Carsten F Boe | Emulsion containing a liquefied propellant gas under pressure and method of spraying same |
| US2526648A (en) * | 1946-08-29 | 1950-10-24 | Freed William Vance | Noncaking ddt powder containing carbon black |
| US2534278A (en) * | 1950-12-19 | Crystallization point depressants | ||
| US2540239A (en) * | 1945-02-05 | 1951-02-06 | Boyle Midway Inc | Insecticidal paint |
| US2556888A (en) * | 1946-08-26 | 1951-06-12 | Sherwin Williams Co | Water reducible 1,1-bis (p-chlorophenyl) 2,2,2 trichloroethane pest control compositions stabilized with methyl cellulose |
| US2556300A (en) * | 1945-10-22 | 1951-06-12 | Standard Oil Dev Co | Insecticidal composition |
| US2568035A (en) * | 1947-04-11 | 1951-09-18 | Goodrich Co B F | Horticultural composition comprising ddt and polyethylene polysulfide |
| US2581174A (en) * | 1945-04-13 | 1952-01-01 | Cross Mary Forbes | Insecticides |
| US2600668A (en) * | 1947-06-12 | 1952-06-17 | Nat Distillers Prod Corp | Insecticidal composition comprising ddt, pyrethrins, and piperonyl butoxide |
| US2786012A (en) * | 1954-01-28 | 1957-03-19 | Calcium Carbonate Company | Compositions and method of producing a calcium carbonate carrier for insecticides |
| US2990321A (en) * | 1958-07-28 | 1961-06-27 | Bornstein Joseph | Bis-(halophenyl)-fluoroaliphatic compounds as ddt synergists |
-
0
- US US22700D patent/USRE22700E/en not_active Expired
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2534278A (en) * | 1950-12-19 | Crystallization point depressants | ||
| US2491632A (en) * | 1944-09-09 | 1949-12-20 | Stauffer Chemical Co | Methods of producing insecticidal compositions containing relatively small quantities of 2,2-bis(p-chlorophenyl) - 1,1,1 - trichlorethane |
| US2452759A (en) * | 1944-09-22 | 1948-11-02 | Velsicol Corp | Insecticide containing methylated naphthalene and 4,4' dichloro-di-phenyl-trichloroethane |
| US2540239A (en) * | 1945-02-05 | 1951-02-06 | Boyle Midway Inc | Insecticidal paint |
| US2581174A (en) * | 1945-04-13 | 1952-01-01 | Cross Mary Forbes | Insecticides |
| US2520551A (en) * | 1945-04-27 | 1950-08-29 | Lowell B Kilgore | N-substituted oxyacetamides |
| US2490958A (en) * | 1945-05-15 | 1949-12-13 | Ciba Ltd | Pest-combating compositions and spraying liquids of enhanced adhering capacity |
| US2515803A (en) * | 1945-05-17 | 1950-07-18 | Segessemann Ernest | Sulfonated 1, 1, 1-trichloro-2,2-bis (p-chlorophenyl) ethane |
| US2442652A (en) * | 1945-06-19 | 1948-06-01 | Us Rubber Co | Insecticides |
| US2448665A (en) * | 1945-06-22 | 1948-09-07 | Elmer E Fleck | Low-temperature noncrystallizing ddt-alkylated naphthalene insecticide |
| US2448405A (en) * | 1945-06-23 | 1948-08-31 | Allied Chem & Dye Corp | Xanthone-ddt insecticide |
| US2442760A (en) * | 1945-07-09 | 1948-06-08 | Dow Chemical Co | Dichlorodiphenyltrichloroethane and cyclohexyldiphenylether insecticidal composition |
| US2430586A (en) * | 1945-07-26 | 1947-11-11 | Sherwin Williams Co | Dihalophenyl alkyl carbinol pesticides |
| US2460377A (en) * | 1945-10-02 | 1949-02-01 | Celanese Corp | Filaments of plasticized lower fatty acid esters of cellulose |
| US2556300A (en) * | 1945-10-22 | 1951-06-12 | Standard Oil Dev Co | Insecticidal composition |
| US2524590A (en) * | 1946-04-22 | 1950-10-03 | Carsten F Boe | Emulsion containing a liquefied propellant gas under pressure and method of spraying same |
| US2510870A (en) * | 1946-05-09 | 1950-06-06 | Dow Chemical Co | Insecticidal composition comprising 1.1-di-(4-chlorophenyl)-2.2.2-trichloro-ethane and 1.1-di-(monochloro-phenyl)-ethane |
| US2556888A (en) * | 1946-08-26 | 1951-06-12 | Sherwin Williams Co | Water reducible 1,1-bis (p-chlorophenyl) 2,2,2 trichloroethane pest control compositions stabilized with methyl cellulose |
| US2526648A (en) * | 1946-08-29 | 1950-10-24 | Freed William Vance | Noncaking ddt powder containing carbon black |
| US2442653A (en) * | 1946-12-10 | 1948-06-01 | Us Rubber Co | Insecticides |
| US2568035A (en) * | 1947-04-11 | 1951-09-18 | Goodrich Co B F | Horticultural composition comprising ddt and polyethylene polysulfide |
| US2600668A (en) * | 1947-06-12 | 1952-06-17 | Nat Distillers Prod Corp | Insecticidal composition comprising ddt, pyrethrins, and piperonyl butoxide |
| US2786012A (en) * | 1954-01-28 | 1957-03-19 | Calcium Carbonate Company | Compositions and method of producing a calcium carbonate carrier for insecticides |
| US2990321A (en) * | 1958-07-28 | 1961-06-27 | Bornstein Joseph | Bis-(halophenyl)-fluoroaliphatic compounds as ddt synergists |
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