DE2111672A1 - Phosphonoglyoxylic acid esters - with insecticidal activity - Google Patents
Phosphonoglyoxylic acid esters - with insecticidal activityInfo
- Publication number
- DE2111672A1 DE2111672A1 DE19712111672 DE2111672A DE2111672A1 DE 2111672 A1 DE2111672 A1 DE 2111672A1 DE 19712111672 DE19712111672 DE 19712111672 DE 2111672 A DE2111672 A DE 2111672A DE 2111672 A1 DE2111672 A1 DE 2111672A1
- Authority
- DE
- Germany
- Prior art keywords
- weight
- parts
- radical
- phosphono
- ester
- 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
- 230000000749 insecticidal effect Effects 0.000 title description 3
- HISRLFWNBVQMKW-UHFFFAOYSA-N 2-oxo-2-phosphonoacetic acid Chemical class OC(=O)C(=O)P(O)(O)=O HISRLFWNBVQMKW-UHFFFAOYSA-N 0.000 title 1
- 150000002148 esters Chemical class 0.000 claims abstract description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 3
- -1 alkyl radical Chemical class 0.000 claims description 11
- 241000238631 Hexapoda Species 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 claims 1
- 150000002912 oxalic acid derivatives Chemical class 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 150000003018 phosphorus compounds Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 5
- 241001490249 Bactrocera oleae Species 0.000 abstract description 2
- 241000255579 Ceratitis capitata Species 0.000 abstract description 2
- 241000953886 Fannia canicularis Species 0.000 abstract description 2
- 241000736227 Lucilia sericata Species 0.000 abstract description 2
- 241000257159 Musca domestica Species 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 239000005949 Malathion Substances 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 229960000453 malathion Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- KBLAMUYRMZPYLS-UHFFFAOYSA-N 2,3-bis(2-methylpropyl)naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 KBLAMUYRMZPYLS-UHFFFAOYSA-N 0.000 description 1
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000257229 Musca <genus> Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 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
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Substances ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 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
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4062—Esters of acids containing the structure -C(=X)-P(=X)(XR)2 or NC-P(=X)(XR)2, (X = O, S, Se)
- C07F9/4065—Esters of acids containing the structure -C(=X)-P(=X)(XR)2, (X = O, S, Se)
-
- 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
- C07F9/1654—Compounds containing the structure P(=X)n-X-acyl, P(=X)n-X-heteroatom, P(=X)n-X-CN (X = O, S, Se; n = 0, 1)
- C07F9/1656—Compounds containing the structure P(=X)n-X-C(=X)- (X = O, S, Se; n = 0, 1)
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3247—Esters of acids containing the structure -C(=X)-P(=X)(R)(XH) or NC-P(=X)(R)(XH), (X = O, S, Se)
- C07F9/3252—Esters of acids containing the structure -C(=X)-P(=X)(R)(XH) or NC-P(=X)(R)(XH), (X = O, S, Se) containing the structure -C(=X)-P(=X)(R)(XR), (X = O, S, Se)
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/409—Compounds containing the structure P(=X)-X-acyl, P(=X) -X-heteroatom, P(=X)-X-CN (X = O, S, Se)
- C07F9/4093—Compounds containing the structure P(=X)-X-C(=X)- (X = O, S, Se)
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5337—Phosphine oxides or thioxides containing the structure -C(=X)-P(=X) or NC-P(=X) (X = O, S, Se)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural 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)
Abstract
Description
Phosphono-glyoxylester Die vorliegende Erfindung betrifft wertvolle neue Phosphonoglyoxylester mit insektizider Wirkung, Schädlingsbekämpfungsmittel, die diese Verbindung als Wirkstoffe enthalten und Verfahren zur Bekämpfung von Schädlingen mit diesen Verbindungen. Phosphono-glyoxyl esters The present invention relates to valuable ones new insecticidal phosphonoglyoxyl esters, pesticides, which contain this compound as active ingredients and methods for controlling pests with these connections.
Es ist bereits bekannt, Phosphorsäureester, bexspielsweìse das O,O-Dimethyl-S(1,2-bis-carbäthoxy-äthyl-)phosphordithloat (Malathion) zur Bekämpfung von Schädlingen zu verwenden.It is already known to use phosphoric acid esters, for example O, O-dimethyl-S (1,2-bis-carbethoxy-ethyl) phosphorodithloate (Malathion) to use to control pests.
Seine Wirkung befriedigt jedoch nicht, Es wurde gefunden, daß Phosphono-glyoxylester der allgemeinen Formel in der R1 und R2 Je einen niederen Alkyl- oder niederen Alkoxyrest und R4 einen niederen Alkoxyrest, einen Phenoxyrest oder einen niederen Dialkylaminorest und n 0 oder 1 bedeutet, eine starke insektizide Wirkung haben. Die Wirkung zeigt sich insbesondere dann, wenn die Stoffe von den Insekten gefressen werden (Fraßgift). Die Verbindungen sind daher insbesondere geeignet zur gezielten Bekämpfung von Insekten, Larven oder Adulten auf ihren Fraßpflanzen oder im Nährboden oder durch Verwendung von Fraßk'ödern, die mit den Wirkstoffen vermischt oder imprägniert sind.However, its effect is unsatisfactory. It has been found that phosphono-glyoxyl esters of the general formula in which R1 and R2 are each a lower alkyl or lower alkoxy radical and R4 is a lower alkoxy radical, a phenoxy radical or a lower dialkylamino radical and n is 0 or 1, have a strong insecticidal effect. The effect is particularly evident when the substances are eaten by the insects (food poison). The compounds are therefore particularly suitable for the targeted control of insects, larvae or adults on their feeding plants or in the nutrient medium or by using feeding baits which are mixed or impregnated with the active ingredients.
Besonders hervorzuheben ist die gute Wirkung bei der Bedämpfung von Musca domestica-, Fannia canicularis, Ceratitis capitata, Dacus oleae und Lucilia sericata.Particularly noteworthy is the good effect when it comes to damping Musca domestica-, Fannia canicularis, Ceratitis capitata, Dacus oleae and Lucilia sericata.
Die neuen Phosphono-glyoxylester der oben genannten Formel können hergestellt werden durch Umsetzung einer Phosphorver-5/71 bindung der Formel in der R1 und R2 die oben genannten Bedeutungen haben und R3 einen Methoxy- oder Äthoxyrest oder Thiomethyl- oder Thioäthylrest bedeutet mit einem Oxalylhalogenidester der Formel in der R4 die oben genannte Bedeutung hat und X Halogen bedeutet. Die Umsetzung kann in Gegenwart oder Abwesenheit von Lösungsmitteln bei Temperaturen zwischen 20 und 130 oC entsprechend der folgenden Reaktionsgleichung durchgeführt werden. The new phosphono-glyoxyl esters of the above formula can be prepared by reacting a phosphorus compound of the formula in which R1 and R2 have the meanings given above and R3 denotes a methoxy or ethoxy radical or thiomethyl or thioethyl radical with an oxalyl halide ester of the formula in which R4 has the abovementioned meaning and X is halogen. The reaction can be carried out in the presence or absence of solvents at temperatures between 20 and 130 oC according to the following reaction equation.
Beispiel 1 25,0 Teile (Gewichtsteile) Trimethylphosphit werden zu einem Gemisch aus 27,5 Teilen Oxalylchloridäthylester und 50 Teilen Benzol langsam zugesetzt. Die Reaktionslösung wird auf einer Temperatur von 25 bis 30°C gehalten und anschlieBend 2 Stunden unter Rückfluß erhitzt. Danach wird das Lösungsmittel abdestilliert und das ReaktXionsgemisch noch 1 Stunde bei 100 oO nachgerührt. Anschließend wird im Vakuum destilliert, das Produkt wird bei 130 OC / 0,02 Torr aufgefangen. Ausbeute: 31,2 Teile C- 74 % d. Th. Es hat folgende Konstitutionsformel In entsprechender Weise können die folgenden Verbindungen hergestellt werden: Kp. n20 D 0,05/1400 1,4535 1,4659 1,4235 1,5172 0,5/1450 1,4407 0,5/145-150° 1,4563 1,4295 0,4/140-144° 1,4302 Die erfindungsgemäßen Wirkstoffe können als Lösungen, Emulsionen, Suspensionen oder Stäubemittel angewendet werden. Die Anwendungsformen richten sich ganz nach den Verwendungszwecken; sie sollen in jedem Fall eine feine Verteilung der wirksamen Substanz gewährleisten.Example 1 25.0 parts (parts by weight) of trimethyl phosphite are slowly added to a mixture of 27.5 parts of oxalyl chloride ethyl ester and 50 parts of benzene. The reaction solution is kept at a temperature of 25 to 30 ° C and then refluxed for 2 hours. The solvent is then distilled off and the reaction mixture is stirred for a further 1 hour at 100,000. It is then distilled in vacuo and the product is collected at 130 ° C./0.02 Torr. Yield: 31.2 parts of C- 74% of theory. Th. It has the following constitutional formula The following connections can be established in a corresponding manner: Kp. N20 D 0.05 / 1400 1.4535 1.4659 1.4235 1.5172 0.5 / 1450 1.4407 0.5 / 145-150 ° 1.4563 1.4295 0.4 / 140-144 1.4302 The active compounds according to the invention can be used as solutions, emulsions, suspensions or dusts. The forms of application depend entirely on the intended use; they should ensure a fine distribution of the active substance in each case.
Zur Herstellung von direkt versprühbaren Lösungen können Kohlenwasserstoffe mit Siedepunkten höher als 150 °C, z. B.Hydrocarbons can be used to produce solutions that can be sprayed directly with boiling points higher than 150 ° C, e.g. B.
Tetrahydronaphthalin oder alkylierte Naphthaline, oder organische Flüssigkeiten mit Siedepunkten höher als 150 °C und einer oder mehreren funktionellen Gruppen, z. B. der Ketogruppe, der Äthergruppe, der Estergruppe oder der Amidgruppe, wobei diese Gruppe als Substituent an einer Kohlenwasserstoffkette stehen oder Bestandteil eines heterocyclischen Ringes sein kann, als Spritzflüssigkeiten verwendet werden.Tetrahydronaphthalene or alkylated naphthalenes, or organic Liquids with boiling points higher than 150 ° C and one or more functional Groups, e.g. B. the keto group, the ether group, the ester group or the amide group, where this group is a substituent on a hydrocarbon chain or is a component a heterocyclic ring can be used as spray liquids.
Wässrige Anwendungsformen können aus Emulsionskonzentraten, Pasten oder netzbaren Pulvern (Spritzpulvern) durch Zusatz von Wasser bereitet werden. Zur Herstellung von Emulsionen können dir Substanzen ale solche oder in einem Lösungsmittel gelöst, mittels Netz- oder Dispergiermitteln, z. B. Polyäthylenoxidadditionsprodukten in Wasser oder organischen Lösungsmitteln homogenisiert werden. Es können aber auch aus wirksamer Substanz, Emulgier- oder Dispergiermittel und eventuell Lösungsmittel bestehende Eonzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind.Aqueous application forms can be made from emulsion concentrates, pastes or wettable powders (wettable powders) can be prepared by adding water. To produce emulsions, you can use substances alone or in a solvent dissolved, by means of wetting or dispersing agents, e.g. B. polyethylene oxide addition products be homogenized in water or organic solvents. But it can also of active substance, emulsifying or dispersing agent and possibly solvent existing concentrates can be produced which are suitable for dilution with water are.
Stäubemittel können durch Nischen oder gemeinsames Vermahlen der wirksamen Substanzen mit einem festen Trägerstoff, z. B.Dusts can be made effective by niching or grinding together Substances with a solid carrier, e.g. B.
Kieselgur, Talkum, Ton oder Düngemittel hergestellt werden.Diatomite, talc, clay or fertilizers can be produced.
Der folgende Versuch erläutert die Anwendung der Wirkstoffe und zeigt ihre Uberlegenheit gegenüber einem bekannten Wirkstoff.The following experiment explains the use of the active ingredients and shows their superiority over a known active ingredient.
Für den Versuch wurden folgende Wirkstoffe verwendet: Malathion (Vergleichsmittel) (erfindungagemäß) (gemäß der Erfindung) Je 100 hungrige Stubenfliegen (Musca domestica) werden in Käfigen von 8 Liter Inhalt 100 mg Milchzucker vermischt mit Wirkstoffsubstanz als Futter geboten. Nach 24 Stunden wird die Mortalitätsrate ermittelt.The following active ingredients were used for the experiment: Malathion (comparative agent) (according to the invention) (according to the invention) For every 100 hungry houseflies (Musca domestica), 100 mg lactose mixed with active substance are offered as feed in 8 liter cages. The mortality rate is determined after 24 hours.
Ergebnis: Wirkstoff Wirkstoffmenge im Milchzucker Mortalität % mg 1. 0,2 96 2. 0,1 100 3. 0,1 100 Die Wirkstoffe 2 und 3 sind bereite in wesentlich geringerer Menge als der Wirkstoff 1 gut wirksam.Result: Active ingredient Amount of active ingredient in lactose mortality% mg 1. 0.2 96 2. 0.1 100 3. 0.1 100 The active ingredients 2 and 3 are already essential less effective than the active ingredient 1.
Beispiel 2 Man vermischt 80 Gewichtsteile der Verbindung 2 mit 20 Gewichtsteilen N-Methyl-α-pyrrolidon und erhält eine Lösung, die zur Ånwndung. in Form kleinster Trophen geeignet ist. Example 2 80 parts by weight of compound 2 are mixed with 20 Parts by weight of N-methyl-α-pyrrolidone and receives a solution that is used for Ånwndung. in the form of the smallest trophies.
Beispiel 3 2O Gewichtsteiie der Verbindung 5 werden in einer Mischung gelöst, die aus 80 Gewichtsteilen Xylol-, 10 Gewichtsteilen des Anlagerungsproduktes von 8 bis 10 Mol Äthylenoxid an 1 Mol Ölsäure-N-monoäthanolamid, 5 Gewichtsteilen Calciumsalz der Dodecylbenzolsulfonsäure und 5 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Äthylenoxid an 1 Mol Ricinusöl besteht. Durch Ausgießen und feines Verteilen der Lösung in lÜO 000 Gewicht steilen Wasser erhalt man eine wässrige Dispersion, die 0,02 Gcwichtsprosent des Wirkstoffs enthält. Example 3 20 parts by weight of compound 5 are in a mixture dissolved, the 80 parts by weight of xylene, 10 parts by weight of the adduct from 8 to 10 moles of ethylene oxide to 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight Calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct consists of 40 moles of ethylene oxide in 1 mole of castor oil. By pouring it out and distributing it finely the solution in 10 000 parts by weight of water gives an aqueous dispersion, which contains 0.02 percent by weight of the active ingredient.
Beispiel 4 20 Gewichtsteile der Verbindung 2 werden in einer Mischung gelöst, die aus 40 Gewichtsteilen Cyclohexanon, 30 Gewichtsteilen Issobutanol, 20 Gewichtsteilen des Anlagerungsproduktes von 7 Mol Äthylenoxid an 1 Mol Isooctylphenol und 10 Gewiahtflteilen des Anlangerungsproduktes von 40 Mol Äthylenoxid an 1 Mol Ricinusöl besteht. Durch EingieBen und feines Verteilen der Lösung in 100 000 Gewichtsteilen Wasser erhält man eine wässrige Dispersion, die 0,02 Gewichtsprozent des Wirkstoffs enthält. Example 4 20 parts by weight of compound 2 are in a mixture dissolved, the 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 Parts by weight of the adduct of 7 moles of ethylene oxide and 1 mole of isooctylphenol and 10 parts by weight of the addition product of 40 moles of ethylene oxide to 1 mole Castor oil consists. By pouring it in and distributing it finely the solution an aqueous dispersion containing 0.02 percent by weight is obtained in 100,000 parts by weight of water contains the active ingredient.
Beispiel 5 20 Gewichtsteile der Verbindung 3 werden in einer Mischung gelöst, die aus 25 Gewichtsteilen Oyclohexanol, 65 Gewichtsteilen einer Mineralölfraktion vom Siedepunkt 210 bis 280 °C und 10 Gewichtsteilen des Anlsgerungsproduktes von 40 Mol Äthylenoxid an 1 Mol Ricinusöl besteht. Durch Eingießen und feines Verteilen der Lösung in 100 000 Gewichtsteilen Wasser erhält man eine wässrige Dispersion, die 0,02 Gewrhtsprozent des Wirkstoffe enthält. Example 5 20 parts by weight of compound 3 are in a mixture dissolved that of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction from the boiling point 210 to 280 ° C and 10 parts by weight of the addition product of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring it in and distributing it finely the solution in 100,000 parts by weight of water gives an aqueous dispersion, which contains 0.02 percent by weight of the active ingredient.
Beispiel 6 20 Gewichtsteile des Wirkstoffe 2 werden mit 3 Gewichtsteilen des Natriumsalzes der Diisobutylnaphtalin-α-sulfonsäure, t7 Gewichtsteilen des Natriumsalzes einer Ligninsulfonsäure aus einer Sulfit-Ablauge und 60 Gewichtsteilen pulverfürmigem Kieselsäuregel gut vermischt and in einer Hammermühle vermahiene Durch feines Verteilen der Mischung in 20 00O Gewichtsteilen Wasser enthält man eine Spritzbrühe, die 0,1 Gewichtsprozent des Wirkstoffs enthält. Example 6 20 parts by weight of active ingredient 2 are mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, t7 parts by weight of the sodium salt of a lignosulphonic acid from a sulphite waste liquor and 60 parts by weight powdery silica gel well mixed and ground in a hammer mill Finely distributing the mixture in 20,000 parts by weight of water yields a spray mixture containing 0.1 percent by weight of the active ingredient.
Beispiel 7 3 Gewichtsteile der Verbindung 9 werden mit 97 Gewichtsteilen feinteiligem Kaolin innig vermischt. Man erhält auf diese Weise ein Stäubemittel, das 5 Gewichtaprozent des Wirkstoffs enthält. Example 7 3 parts by weight of compound 9 become 97 parts by weight finely divided kaolin intimately mixed. In this way a dust is obtained which contains 5 percent by weight of the active ingredient.
Beispiel 8 30 Gewichtsteile der Verbindung 2 werden mit einer Mischung aus 92 Gewichtsteilen pulverförmigem Kieselsäuregel und 8 Gewichtsteilen Paraffinöl, das auf die Oberfläche dieses Kieselsäuregels gesprüht wurde, iuning vermischt. Man erhält auf diese Weise eine Aufbereitung des Wirkstoffs mit guter Haftfähigkeit. Example 8 30 parts by weight of compound 2 are mixed with a mixture from 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil, which was sprayed onto the surface of this silica gel, iuning mixed. In this way, a preparation of the active ingredient with good adhesion is obtained.
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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DE19712111672 DE2111672A1 (en) | 1971-03-11 | 1971-03-11 | Phosphonoglyoxylic acid esters - with insecticidal activity |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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DE19712111672 DE2111672A1 (en) | 1971-03-11 | 1971-03-11 | Phosphonoglyoxylic acid esters - with insecticidal activity |
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DE2111672A1 true DE2111672A1 (en) | 1972-09-21 |
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DE19712111672 Pending DE2111672A1 (en) | 1971-03-11 | 1971-03-11 | Phosphonoglyoxylic acid esters - with insecticidal activity |
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DE (1) | DE2111672A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0106114A2 (en) * | 1982-09-10 | 1984-04-25 | Hoechst Aktiengesellschaft | Functional derivatives of acetic acid containing phosphorus, process for preparing them and herbicidal and growth regulating compositions containing them |
EP0196026A1 (en) * | 1985-03-28 | 1986-10-01 | Hoechst Aktiengesellschaft | Functional derivatives of phosphorus containing acetic acids, process for their preparation and herbicidal and plant growth regulator composition containing them |
WO2003011221A2 (en) * | 2001-07-30 | 2003-02-13 | University Of Southern California | PREPARATION AND USE OF α-KETO PHOSPHONATES |
-
1971
- 1971-03-11 DE DE19712111672 patent/DE2111672A1/en active Pending
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0106114A2 (en) * | 1982-09-10 | 1984-04-25 | Hoechst Aktiengesellschaft | Functional derivatives of acetic acid containing phosphorus, process for preparing them and herbicidal and growth regulating compositions containing them |
EP0106114A3 (en) * | 1982-09-10 | 1984-07-18 | Hoechst Aktiengesellschaft | Functional derivatives of acetic acid containing phosphorus, process for preparing them and herbicidal and growth regulating compositions containing them |
US4594098A (en) * | 1982-09-10 | 1986-06-10 | Hoechst Aktiengesellschaft | Phosphorus-containing functional derivatives of acetic acid, process for their preparation and herbicidal and growth-regulating agents containing them |
EP0196026A1 (en) * | 1985-03-28 | 1986-10-01 | Hoechst Aktiengesellschaft | Functional derivatives of phosphorus containing acetic acids, process for their preparation and herbicidal and plant growth regulator composition containing them |
WO2003011221A2 (en) * | 2001-07-30 | 2003-02-13 | University Of Southern California | PREPARATION AND USE OF α-KETO PHOSPHONATES |
WO2003011221A3 (en) * | 2001-07-30 | 2003-07-24 | Univ Southern California | PREPARATION AND USE OF α-KETO PHOSPHONATES |
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