DE1211146B - Process for the preparation of thiophosphoric acid esters - Google Patents
Process for the preparation of thiophosphoric acid estersInfo
- Publication number
- DE1211146B DE1211146B DEST20444A DEST020444A DE1211146B DE 1211146 B DE1211146 B DE 1211146B DE ST20444 A DEST20444 A DE ST20444A DE ST020444 A DEST020444 A DE ST020444A DE 1211146 B DE1211146 B DE 1211146B
- Authority
- DE
- Germany
- Prior art keywords
- acid esters
- preparation
- thiophosphoric acid
- general formula
- low molecular
- 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
- 238000000034 method Methods 0.000 title claims description 8
- 150000003580 thiophosphoric acid esters Chemical class 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- GYXHHICIFZSKKZ-UHFFFAOYSA-N 2-sulfanylacetamide Chemical compound NC(=O)CS GYXHHICIFZSKKZ-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 241000238631 Hexapoda Species 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 241000257159 Musca domestica Species 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 241000238675 Periplaneta americana Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- -1 dithiophosphoric acid ester Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 235000013312 flour Nutrition 0.000 description 5
- 231100000167 toxic agent Toxicity 0.000 description 5
- 241000258913 Oncopeltus fasciatus Species 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 231100000518 lethal Toxicity 0.000 description 3
- 230000001665 lethal effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000003440 toxic substance Substances 0.000 description 3
- 241000255925 Diptera Species 0.000 description 2
- 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 2
- 241000257226 Muscidae Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 241001454295 Tetranychidae Species 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- JDFDHBSESGTDAL-UHFFFAOYSA-N 3-methoxypropan-1-ol Chemical compound COCCCO JDFDHBSESGTDAL-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 244000207543 Euphorbia heterophylla Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000184861 Juglans nigra Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 229920003091 Methocel™ Polymers 0.000 description 1
- NSJNRJYQQPRCLF-UHFFFAOYSA-N N-methyl-2-sulfanylacetamide Chemical compound CNC(=O)CS NSJNRJYQQPRCLF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241001510001 Periplaneta brunnea Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000007529 inorganic bases Chemical class 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
- 239000003350 kerosene Substances 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229940096992 potassium oleate Drugs 0.000 description 1
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 1
- ARENMZZMCSLORU-UHFFFAOYSA-N propan-2-yl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OC(C)C)=CC=CC2=C1 ARENMZZMCSLORU-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Verfahren zur Herstellung von Thiophosphorsäureestern Die Erfindung betrifft ein Verfahren zur Herstellung von Thiophosphorsäureestern der allgemeinen Formel in der R eine niedermolekulare Alkylgruppe, z. B. die Methyl-, Äthyl-, n-Propyl-, Isobutyl- oder n-Butylgruppe, und R1 und R2 ein Wasserstoffatom oder eine niedermolekulare Alkylgruppe bedeuten.Process for the preparation of thiophosphoric acid esters The invention relates to a process for the preparation of thiophosphoric acid esters of the general formula in which R is a low molecular weight alkyl group, e.g. B. the methyl, ethyl, n-propyl, isobutyl or n-butyl group, and R1 and R2 represent a hydrogen atom or a low molecular weight alkyl group.
Die Thiophosphorsäureester werden in an sich bekannter Weise durch
Umsetzen von etwa 1 Mol einer O,O-Dialkyl-S-halogenmethylthionothiolphosphorsäure
mit etwa 1 Mol eines 2-Mercaptoacetamids hergestellt. Die Umsetzung wird durch das
folgende Reaktionsschema dargestellt:
Äthylenglykolmonoäthyläther, Propylenglykolmonomethyläther, Trimethylenglykolmonomethyläther, verwendet. Als basische Kondensationsmittel werden vorzugsweise anorganische Basen, wie Alkalimetallcarbonate, z. B. Natriumcarbonat und Kaliumcarbonat, Alkalimetallhydroxyde, z. B. Natriumhydroxyd und Kaliumhydroxyd, verwendet.Ethylene glycol monoethyl ether, propylene glycol monomethyl ether, trimethylene glycol monomethyl ether, used. The basic condensation agents are preferably inorganic bases, such as alkali metal carbonates, e.g. B. sodium carbonate and potassium carbonate, alkali metal hydroxides, z. B. sodium hydroxide and potassium hydroxide are used.
Beispiel 1 4,0 g Natriumhydroxyd werden in 10 ccm Wasser gelöst und zu 90 ccm denaturiertem Athylalkohol gegeben; die erhaltene Lösung wird mit Schwefelwasserstoff gesättigt, wobei Natriumhydrosulfid erhalten wird. 4,7 g 2-Chloracetamid werden zu der Natriumhydrosulfidlösung gegeben, und das erhaltene Gemisch wird 1/2 Stunde am Rückflußkühler erhitzt; dann werden 11,7 g O,O-Diäthyl-S-chlormethylthionothiolphosphorsäure in das Reaktions--gemisch eingeführt und dieses 2 Stunden am Rückflußkühler erhitzt. Nach dem Abkühlen der Mischung auf Raumtemperatur wird das Reaktionsprodukt in 200 ccm Wasser gegossen und das wäßrige Gemisch mit Benzol extrahiert. Der organische Extrakt wird über wasserfreiem Magnesiumsulfat getrocknet und filtriert; das Lösungsmittel wird dann bei.verringertem Druck abdestilliert, und es wird-ein sHchwachgelbes Öl mit einem Brechungsindex n25 von 1,5616 erhalten. Die Ausbeute beträgt 700/0.example 1 4.0 g of sodium hydroxide are dissolved in 10 cc of water and added to 90 cc of denatured ethyl alcohol; the resulting solution is saturated with hydrogen sulfide to give sodium hydrosulfide. 4.7 g of 2-chloroacetamide are added to the sodium hydrosulfide solution and the resulting mixture is refluxed for 1/2 hour; then 11.7 g of O, O-diethyl-S-chloromethylthionothiolphosphoric acid are introduced into the reaction mixture and this is heated under the reflux condenser for 2 hours. After the mixture has cooled to room temperature, the reaction product is poured into 200 cc of water and the aqueous mixture is extracted with benzene. The organic extract is dried over anhydrous magnesium sulfate and filtered; the solvent is then distilled off at reduced pressure, and a pale yellow oil with a refractive index n25 of 1.5616 is obtained. The yield is 700/0.
Beispiel 2 Natriumäthylat wird durch Lösen von 1,13 g Natrium in 80 ccm Äthanol hergestellt. In diese Lösung werden zunächst 5,3 - g 2-Mercapto-N-methylacetamid und dann 11,7 g O,O-Diäthyl-S-chlormethylthionothiolphosphorsäure gegeben; das erhaltene Gemisch wird 4 Stunden am Rückflußkühler erhitzt.Example 2 Sodium ethylate is prepared by dissolving 1.13 g of sodium in 80 cc of ethanol. First 5.3 g of 2-mercapto-N-methylacetamide and then 11.7 g of O, O-diethyl-S-chloromethylthionothiolphosphoric acid are added to this solution; the resulting mixture is refluxed for 4 hours.
Nach dem Abkühlen der Reaktionsmischung auf Raumtemperatur wird filtriert und das Filtrat unter vermindertem Druck destilliert, wobei der Rückstand in dem Destillierkolben 140"C bei 20 mm nicht überschreitet. Es werden 11 g eines orangefarbigen Ols mit einem Brechungsindex n205 von 1,5424 erhalten.After the reaction mixture has cooled to room temperature, it is filtered and the filtrate is distilled under reduced pressure, the residue in the Alembic does not exceed 140 "C at 20 mm. It will be 11 g of an orange Ols with a refractive index n205 of 1.5424 were obtained.
Die nach dem Verfahren der Erfindung herstellbaren Thiophosphorsäureester sind wirksam bei der Bekämpfung von verschiedenen Pflanzenkrankheiten, die durch niedere Insekten, z. B. Küchenschaben, Oncopeltus fasciatus, amerikanische Reismehlkäfer, Hausfliegen, Gewächshausspinnmilben, hervorgerufen werden. Die Verbindungen können unmittelbar auf den ausgewachsenen Organismus des Krankheitsträgers und in einigen Fällen auf die Eier aufgebracht werden. In beiden Fällen wird der Organismus des Krankheitsträgers getötet oder bekämpft. The thiophosphoric acid esters which can be prepared by the process of the invention are effective in combating various plant diseases caused by lower insects, e.g. B. Cockroaches, Oncopeltus fasciatus, American flour beetle, House flies, greenhouse spider mites. The connections can directly on the adult organism of the disease carrier and in some Cases to be applied to the eggs. In both cases the organism of the Carrier killed or fought.
Das Einarbeiten der toxischen Verbindungen in geeignete pestizide Mischungen erfolgt in bekannter Weise. Als Trägerstoffe für die herstellbaren Verbindungen können beispielsweise Talkum, natürlich vorkommende Tonerde, Diatomeenerde, verschiedene Mehle, z. B. Walnußschalenmehl, Weizenmehl, Soja- -bohnenmehl, oder Baumwollsamen verwendet werden. Incorporating the toxic compounds into appropriate pesticides Mixing takes place in a known manner. As a carrier for the compounds that can be produced For example, talc, naturally occurring clay, diatomaceous earth, various Flours, e.g. B. walnut shell flour, wheat flour, soy bean flour, or cottonseed be used.
Die herstellbaren Verbindungen können auch als Lösung oder Dispersion verwendet werden. So kann man sie in einem Lösungsmittel, z. B. Kerosin Schweröl, Xylol oder alkylierten Naphthalinen, lösen und diese organischen Lösungen unmittelbar verwenden. Meistens werden jedoch wäßrige Dispersionen verwendet, die durch Dispergieren einer konzentrierten Lösung der toxischen Verbindungen in einem geeigneten organischen Lösungsmittel in Wasser meistens mit Hilfe von oberflächenaktiven Mitteln erhalten werden. Als oberflächenaktive Mittel, die anionisch, kationisch oder nichtionisch sein können, werden z. B. Natriumstearat, Kaliumoleat und andere alkalische Metallseifen und Detergentien,-wie Natriumlaurylsulfat, Natriumnaphthalin- sulfonat, Natriumalkylnaphthalinsulfonat, Methylcellulose, Fettalkoholäther, Polyglykolfettsäureester und andere polyoxyäthylenoberflächenaktive Mittel, verwendet. Der Mengenanteil dieser Mittel beträgt meistens 1 bis 15 Gewichtsprozent, bezogen auf die toxische Verbindung. The compounds that can be produced can also be used as a solution or dispersion be used. So you can in a solvent such. B. Kerosene heavy oil, Xylene, or alkylated naphthalenes, dissolve and these organic solutions immediately use. In most cases, however, aqueous dispersions are used which are produced by dispersing a concentrated solution of the toxic compounds in a suitable organic Solvents in water mostly obtained with the help of surfactants will. As surfactants that are anionic, cationic or nonionic can be z. B. sodium stearate, potassium oleate and other alkaline metal soaps and detergents, such as sodium lauryl sulfate, sodium naphthalene sulfonate, sodium alkylnaphthalene sulfonate, Methyl cellulose, fatty alcohol ethers, polyglycol fatty acid esters and other polyoxyethylene surfactants Means, used. The proportion of these agents is usually 1 to 15 percent by weight, based on the toxic compound.
Acaricidtest: Gewächshausspinnmilben, Tetranychus telarius (Linn.), werden bei den Acaricidtests verwendet. Junge Pintobohnenpflanzeli werden mit mehreren hundert Milben infiziert. Dispersionen der Testverbindungen werden durch Lösen von 0,1 g der toxischen Verbindung in 10 ccm Aceton hergestellt. Diese Lösung wird dann mit Wasser, das 0,0150in »VATSOL« (Natriumsalz von Isopropylnaphthalinsulfonat) und 0,0050/o »METHOCEL« (methylierte Zellulose) als Emulgierungsmittel enthält, mit so viel Wasser verdünnt, daß sich Konzentrationen des aktiven Bestandteils von 0,25 bis 0,0050in ergeben. Die Testsuspensionen werden dann auf die infizierten Pintobohnenpflanzen aufgesprüht. Acaricid test: greenhouse spider mites, Tetranychus telarius (Linn.), are used in the acaricid tests. Young pinto bean plants are made with several a hundred mites infected. Dispersions of the test compounds are made by dissolving 0.1 g of the toxic compound in 10 cc of acetone prepared. This solution then becomes with water, which is 0.0150 in "VATSOL" (sodium salt of isopropylnaphthalene sulfonate) and 0.0050 / o »METHOCEL« (methylated cellulose) as an emulsifying agent, diluted with so much water that concentrations of the active ingredient of 0.25 to 0.0050in. The test suspensions are then applied to the infected Pinto bean plants sprayed on.
Nach 7 und 14 Tagen werden die Pflanzen sowohl auf postembryonale Formen der Milbe als auch auf Eier untersucht. Der Prozentsatz der Abtötungen wird durch Vergleich mit Kontrollpflanzen bestimmt, die nicht besprüht wurden, und die 500/oige tödliche Menge wird auf Grund von bekannten Verfahren berechnet. In der nachfolgenden Tabelle sind die Werte für die 500/oige tödliche Menge angegeben.After 7 and 14 days the plants are both postembryonic Forms of the mite and eggs were examined. The percentage of killings will be determined by comparison with control plants that were not sprayed, and the 500% lethal amount is calculated on the basis of known methods. In the The table below shows the values for the 500% lethal amount.
Insektiiidtest: Drei Insektenarten werden dem Insektizidtest unterworfen: 1. Hausfliege (HF) Musca domestica (Linn.) 2. Amerikanische Küchenschabe (AR) Periplaneta americana (Linn.) 3. Oncopeltus fasciatus (MWB) Oncopeltus fasciatus (Dallas) Das bei den Insekten angewendete Verfahren entspricht dem Milbentestverfahren. Die Testinsekten werden in Papphülsen mit einem Durchmesser von 7,8 cm und einer Höhe von 4 cm gegeben. Die Käfige sind mit Zellophanböden und perforierten Deckeln versehen. Es werden 10 bis 25 Insekten je Käfig verwendet. Nahrung und Wasser werden in jeden Käfig gegeben. Die in den Käfigen befindlichen Insekten werden mit der aktiven Verbindung bei verschiedenen Konzentrationen besprüht. Nach 24 und 72 Stunden werden Auszählungen vorgenommen, um die lebenden und toten Insekten zu bestimmen. Insecticide test: Three types of insects are subjected to the insecticide test: 1. House fly (HF) Musca domestica (Linn.) 2. American cockroach (AR) Periplaneta americana (Linn.) 3. Oncopeltus fasciatus (MWB) Oncopeltus fasciatus (Dallas) Das The method used on the insects corresponds to the mite test method. The test insects are placed in cardboard tubes with a diameter of 7.8 cm and a height of 4 cm. The cages have cellophane bottoms and perforated lids. It will 10 to 25 insects used per cage. Food and water are in each cage given. The insects in the cages will be with the active compound sprayed at different concentrations. After 24 and 72 hours, there are counts made to determine the living and dead insects.
Der unter Verwendung von Hausfliegen vorgenommene Test weicht folgendermaßen ab: Die toxische Verbindung wird in einem flüchtigen Lösungsmittel, vorzugsweise Aceton, gelöst, die aktive Verbindung wird in eine Petrischale pipettiert, luftgetrocknet und in eine Papphülse gegeben. Fünfundzwanzig weibliche Fliegen werden in die Hülse eingesperrt. Die Fliegen werden kontinuierlich dem bekannten Rückstand der aktiven Verbindung, der sich in dem Käfig befindet, ausgesetzt. Nach 24 und 48 Stunden werden Auszählungen vorgenommen, um die lebenden und toten Insekten zu bestimmen: Die Werte fur die 500/oige tödliche Menge werden nach bekannten Verfahren errechnet. Die nach den Beispielen 1 und 2 herstellbaren Verbindungen wurden mit der aus Beispiel 7 der deutschen Auslegeschrift 1123 863 bekannten Verbindung verglichen. The test made using house flies deviates as follows ab: The toxic compound is in a volatile solvent, preferably Acetone, dissolved, the active compound is pipetted into a Petri dish, air-dried and put in a cardboard tube. Twenty-five female flies are poded locked up. The flies are continuously the known residue of the active Compound, which is located in the cage, exposed. After 24 and 48 hours will be Counts are made to determine the live and dead insects: the values for the 500% lethal amount are calculated according to known methods. The after Compounds which can be prepared in Examples 1 and 2 were compared with that of Example 7 the German Auslegeschrift 1123 863 known connection compared.
Vergleichsversuche
AR Amerikanische Küchenschabe (Periplaneta americana). AR American cockroach (Periplaneta americana).
MWB WolfsmilchkäTer (Oncopeltus fasciatus).MWB milkweed box (Oncopeltus fasciatus).
2 SM Zweifleckmilbe (Tetranychus telarius). 2 SM two-spot mite (Tetranychus telarius).
* Milligramm je Kilogramm des Körpergewichts der eingesetzten Ratten. * Milligrams per kilogram of the body weight of the rats used.
** Xlg = Mikrogramm.** Xlg = micrograms.
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DE1123863B (en) * | 1958-01-28 | 1962-02-15 | Rhone Poulenc Sa | Pest repellent with insecticidal and acaricidal effects |
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DE1123863B (en) * | 1958-01-28 | 1962-02-15 | Rhone Poulenc Sa | Pest repellent with insecticidal and acaricidal effects |
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