DE1174104B - Insecticides - Google Patents
InsecticidesInfo
- Publication number
- DE1174104B DE1174104B DEB64999A DEB0064999A DE1174104B DE 1174104 B DE1174104 B DE 1174104B DE B64999 A DEB64999 A DE B64999A DE B0064999 A DEB0064999 A DE B0064999A DE 1174104 B DE1174104 B DE 1174104B
- Authority
- DE
- Germany
- Prior art keywords
- minutes
- parts
- formula
- substance
- active ingredients
- 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
- 239000002917 insecticide Substances 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- 241000257226 Muscidae Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 150000003580 thiophosphoric acid esters Chemical class 0.000 description 2
- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- FYRVMZSKWATEMP-UHFFFAOYSA-N 4-bromo-2,5-dichlorophenol;sodium Chemical compound [Na].OC1=CC(Cl)=C(Br)C=C1Cl FYRVMZSKWATEMP-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000238631 Hexapoda Species 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000008096 xylene 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Internat. Kl.: A Ol ηBoarding school Class: A Ol η
Deutsche Kl.: 451-9/36 German class: 451-9 / 36
Nummer: 1174 104Number: 1174 104
Aktenzeichen: B 64999 IV a / 451File number: B 64999 IV a / 451
Anmeldetag: 30. November 1961Filing date: November 30, 1961
Auslegetag: 16. Juli 1964Opening day: July 16, 1964
Die Erfindung betrifft insektizide Mittel, die als Wirkstoff eine oder mehrere Verbindungen der allgemeinen Formel IThe invention relates to insecticidal compositions which, as active ingredients, contain one or more compounds of the general Formula I.
RiORiO
R2OR 2 O
enthalten. In dieser Formel bedeuten Ri und Ra die Methyl- oder die Äthylgruppe.contain. In this formula, Ri and Ra mean the methyl or the ethyl group.
Es wurde gefunden, daß die erfindungsgemäßen Verbindungen hervorragende insektizide Mittel sind, insbesondere in ihrer Dauerwirkung gegenüber Insekten. Sie sind wesentlich besser wirksam als strukturell sehr ähnlich gebaute bekannte Verbindungen. Beispielsweise wurde die Wirksamkeit des O,O-Dimethyl - O - 2,5 - dichlor - 4 - bromphenylthiophosphats (Substanz 2) gegen Hausfliegen vergleichend gegenüber der Wirksamkeit des bekannten 0,0-Dimethyl - O - 2,4,5 - trichlorphenylthiophosphats (Substanz 1) bei verschiedenen Konzentrationen getestet. Dabei wurden wäßrige Suspensionen der Wirkstoffe Insektizide MittelIt has been found that the compounds according to the invention are excellent insecticidal agents, especially in their long-term effect on insects. They are much more effective than structurally very similar known connections. For example, the effectiveness of the O, O-dimethyl - O - 2,5 - dichloro - 4 - bromophenyl thiophosphate (Substance 2) against house flies compared to the effectiveness of the known 0,0-dimethyl - O - 2,4,5 - trichlorophenylthiophosphate (substance 1) tested at different concentrations. Aqueous suspensions of the active ingredients were used as insecticidal agents
Anmelder:Applicant:
C. H. Boehringer Sohn, Ingelheim/RheinC. H. Boehringer Sohn, Ingelheim / Rhine
Als Erfinder benannt:Named as inventor:
Dr. Richard Sehring,Dr. Richard Sehring,
Dr. Karl Zeile, Ingelheim/RheinDr. Karlzeile, Ingelheim / Rhine
auf Filtrierpapier aufgetragen und das Wasser abgedampft. Auf das so behandelte Papier wurden Hausfliegen sofort oder nach bestimmten Zeitabständen aufgebracht und die LT50 bestimmt. Unter der LT50 versteht man die Zeit, in der 50% der Tiere getötet wurden.applied to filter paper and the water evaporated. On the paper treated in this way House flies applied immediately or after certain time intervals and the LT50 determined. Under the LT50 means the time in which 50% of the animals were killed.
Das Ergebnis dieser Vergleichsversuche geht aus folgender Tabelle hervor:The result of these comparative tests is shown in the following table:
Substanz 1
Substanz 2Substance 1
Substance 2
Substanz 1
Substanz 2Substance 1
Substance 2
Konzentrationconcentration
1%1%
1%1%
2,5%2.5%
Sofort
LT50 Immediately
LT 50
130 Minuten
110 Minuten130 minutes
110 minutes
70 Minuten
60 Minuten Woche
LT50 70 minutes
60 minutes a week
LT 50
Minuten
MinutenMinutes
Minutes
Minuten
MinutenMinutes
Minutes
2 Wochen
LT502 weeks
LT50
250 Minuten
200 Minuten250 minutes
200 minutes
240 Minuten
160 Minuten240 minutes
160 minutes
3 Wochen LT60 3 weeks LT 60
290 Minuten 230 Minuten290 minutes 230 minutes
250 Minuten 190 Minuten250 minutes 190 minutes
4 Wochen LT60 4 weeks LT 60
500 Minuten 400 Minuten500 minutes 400 minutes
500 Minuten 250 Minuten500 minutes 250 minutes
Neben der überlegenen Dauerwirkung der beanspruchten Wirkstoffe zeigen dieselben zusätzlich eine besonders geringe Toxizität gegenüber Warmblütern. Die LD50 (weiße Maus, ρ. ο.) liegt durchschnittlich über 2000 mg/kg.In addition to the superior long-term effect of the claimed active ingredients, they also show a particularly low toxicity to warm-blooded animals. The LD50 (white mouse, ρ. Ο.) Is average over 2000 mg / kg.
Die Anwendung der neuen Wirkstoffe erfolgt in der in der Schädlingsbekämpfung üblichen Weise. Die Wirkstoffe können für sich allein oder in Mischung mit anderen Wirkstoffen, z. B. in Form von Suspensionen, Lösungen, Streupulvern oder Pasten zur Anwendung gelangen. Die bevorzugte Wirkstoffkonzentration beträgt 0,01 bis 3%.The new active ingredients are used in the manner customary in pest control. the Active ingredients can be used alone or in a mixture with other active ingredients, e.g. B. in the form of suspensions, Solutions, powders or pastes are used. The preferred concentration of active ingredient is 0.01 to 3%.
Die Herstellung der neuen Thiophosphorsäureester der Formel I erfolgt in an sich bekannter Weise, z. B. durch Umsetzung der Alkalisalze von Phenolen der allgemeinen Formel IIThe new thiophosphoric acid esters of the formula I are prepared in a manner known per se, for. B. by reacting the alkali salts of phenols of the general formula II
ClCl
HOHO
mit OjO-Dialkylthiophosphorsäurechlorid. Die Reak-with OjO-dialkylthiophosphoric acid chloride. The Rea-
409 630/377409 630/377
tion wird in einem inerten organischen Lösungsmittel, beispielsweise Chlorbenzol, bei erhöhten Temperaturen, vorzugsweise bei 40 bis 12O0C, vorgenommen. Zu den Verbindungen der Formel I gelangt man auch, wenn man Thiophosphorsäuredichlorid der Formel IIItion is, for example, at elevated temperatures, made in an inert organic solvent chlorobenzene preferably at 40 to 12O 0 C. The compounds of the formula I can also be obtained if thiophosphoric acid dichloride of the formula III
IOIO
mit Alkoholaten umsetzt.with alcoholates.
Die neuen Thiophosphorsäureester der Formel I sind zum Teil farblose Öle, zum Teil kristalline Substanzen. The new thiophosphoric acid esters of the formula I are partly colorless oils and partly crystalline substances.
Der O^-Dimethyl-O^S-dichlor^-bromphenylthiophosphorsäureester wird beispielsweise folgendermaßen hergestellt:The O ^ -Dimethyl-O ^ S-dichloro ^ -bromophenylthiophosphoric acid ester is made, for example, as follows:
272,9 g2,5-Dichlor-4-bromphenolnatrium (1,0MoI) werden in 700 ecm Chlorbenzol suspendiert und mit 176,6 g Ο,Ο-Dimethylthiophosphorsäurechlorid (1,1 Mol) versetzt und unter Rühren 8 Stunden auf 10O0C erhitzt. Dem Reaktionsansatz wurden 5 g Kaliumbromid als Katalysator hinzugefügt.272.9 g of 2,5-dichloro-4-bromophenol sodium (1.0 mol) are suspended in 700 ecm of chlorobenzene, and 176.6 g of Ο, Ο-dimethylthiophosphoric acid chloride (1.1 mol) are added and the mixture is kept at 10O 0 C for 8 hours with stirring heated. 5 g of potassium bromide were added as a catalyst to the reaction mixture.
Nach beendeter Umsetzung wird vom Kochsalz abfiltriert, die Lösung mit verdünnter Natronlauge gewaschen und anschließend mit Natriumsulfat getrocknet. Nach Abdestillieren des Chlorbenzols erhält man ein farbloses Öl.After the reaction has ended, the sodium chloride is filtered off and the solution is washed with dilute sodium hydroxide solution washed and then dried with sodium sulfate. Obtains after distilling off the chlorobenzene one colorless oil.
Ausbeute an Rohprodukt: 95% der Theorie. Die Reinigung erfolgt durch Destillation. Kp.0,01 140 bis 142° C.Yield of crude product: 95% of theory. The purification is carried out by distillation. Bp 0.01 140 up to 142 ° C.
Die folgenden Beispiele sollen die Erfindung näher erläutern.The following examples are intended to explain the invention in more detail.
StäubemittelDust
2 Teile Wirkstoff werden auf 98 Teile Kaolin aufgedüst und homogen vermählen.2 parts of active ingredient are sprayed onto 98 parts of kaolin and ground homogeneously.
SuspensionsmittelSuspending agent
25 Teile Wirkstoff werden auf 73 Teile Kieselgur aufgedüst und nach Zusatz von 2 Teilen naphthalinsulfonsäuren! Natrium homogen vermählen. Diese Mischung wird mit Wasser bis zur gewünschten Konzentration versetzt.25 parts of active ingredient are sprayed onto 73 parts of kieselguhr and, after adding 2 parts of naphthalenesulfonic acids! Grind the sodium homogeneously. This mixture is mixed with water until desired Concentration shifted.
Beispiel 3 EmulsionExample 3 Emulsion
20 Teile Wirkstoff werden in 75 Teilen Xylol gelöst und 5 Teile Ricinolbutylestersulfonat zugesetzt. Diese Lösung wird in Wasser bis zur gewünschten Konzentration suspendiert.20 parts of active ingredient are dissolved in 75 parts of xylene and 5 parts of ricinol butyl ester sulfonate are added. These Solution is suspended in water to the desired concentration.
Claims (1)
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE625198D BE625198A (en) | 1961-11-30 | ||
NL123753D NL123753C (en) | 1961-11-30 | ||
NL286081D NL286081A (en) | 1961-11-30 | ||
DEB64999A DE1174104B (en) | 1961-11-30 | 1961-11-30 | Insecticides |
CH1352062A CH416210A (en) | 1961-11-30 | 1962-11-19 | Pesticides |
GB44057/62A GB956343A (en) | 1961-11-30 | 1962-11-21 | Halophenyl thiophosphates |
FR916346A FR1344586A (en) | 1961-11-30 | 1962-11-22 | Insecticides |
BR145028/62A BR6245028D0 (en) | 1961-11-30 | 1962-11-29 | PROCESS FOR THE PREPARATION OF NEW THIOPHOSPHORIC AND COMPOSITE ESTERS PERMITTED THROUGH THESE |
OA50125A OA00144A (en) | 1961-11-30 | 1964-05-27 | Insecticides. |
US502302A US3275718A (en) | 1961-11-30 | 1965-10-22 | O, o-dialkyl-o-(2, 5-dichloro-4-bromophenyl)-thiophosphates |
MY76/65A MY6500076A (en) | 1961-11-30 | 1965-12-30 | Halophenyl thiophosphates |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB64999A DE1174104B (en) | 1961-11-30 | 1961-11-30 | Insecticides |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1174104B true DE1174104B (en) | 1964-07-16 |
Family
ID=6974600
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEB64999A Pending DE1174104B (en) | 1961-11-30 | 1961-11-30 | Insecticides |
Country Status (8)
Country | Link |
---|---|
BE (1) | BE625198A (en) |
BR (1) | BR6245028D0 (en) |
CH (1) | CH416210A (en) |
DE (1) | DE1174104B (en) |
GB (1) | GB956343A (en) |
MY (1) | MY6500076A (en) |
NL (2) | NL123753C (en) |
OA (1) | OA00144A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH466276A (en) * | 1964-11-20 | 1968-12-15 | Ciba Geigy | Process for the production of new aromatic phosphoric acid esters or phosphonic acid esters |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1025199B (en) * | 1950-03-30 | 1958-02-27 | Dow Chemical Co | Pest repellants |
DE1099530B (en) * | 1959-01-07 | 1961-02-16 | Bayer Ag | Process for the preparation of chlorine-substituted alkylthionophosphonic acid-O-alkyl-O-phenyl esters |
-
0
- NL NL286081D patent/NL286081A/xx unknown
- BE BE625198D patent/BE625198A/xx unknown
- NL NL123753D patent/NL123753C/xx active
-
1961
- 1961-11-30 DE DEB64999A patent/DE1174104B/en active Pending
-
1962
- 1962-11-19 CH CH1352062A patent/CH416210A/en unknown
- 1962-11-21 GB GB44057/62A patent/GB956343A/en not_active Expired
- 1962-11-29 BR BR145028/62A patent/BR6245028D0/en unknown
-
1964
- 1964-05-27 OA OA50125A patent/OA00144A/en unknown
-
1965
- 1965-12-30 MY MY76/65A patent/MY6500076A/en unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1025199B (en) * | 1950-03-30 | 1958-02-27 | Dow Chemical Co | Pest repellants |
DE1099530B (en) * | 1959-01-07 | 1961-02-16 | Bayer Ag | Process for the preparation of chlorine-substituted alkylthionophosphonic acid-O-alkyl-O-phenyl esters |
Also Published As
Publication number | Publication date |
---|---|
BR6245028D0 (en) | 1973-05-15 |
CH416210A (en) | 1966-06-30 |
OA00144A (en) | 1966-03-15 |
NL286081A (en) | |
BE625198A (en) | |
MY6500076A (en) | 1965-12-31 |
NL123753C (en) | |
GB956343A (en) | 1964-04-22 |
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