DE1964921A1 - Phenyl phosphonate pesticides with insecti- - cidal and acaricidal activity - Google Patents
Phenyl phosphonate pesticides with insecti- - cidal and acaricidal activityInfo
- Publication number
- DE1964921A1 DE1964921A1 DE19691964921 DE1964921A DE1964921A1 DE 1964921 A1 DE1964921 A1 DE 1964921A1 DE 19691964921 DE19691964921 DE 19691964921 DE 1964921 A DE1964921 A DE 1964921A DE 1964921 A1 DE1964921 A1 DE 1964921A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- pesticides
- insecti
- cidal
- alkyl
- 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
- 239000000575 pesticide Substances 0.000 title claims abstract description 5
- 230000000895 acaricidal effect Effects 0.000 title description 2
- 230000000749 insecticidal effect Effects 0.000 title description 2
- QLZHNIAADXEJJP-UHFFFAOYSA-L dioxido-oxo-phenyl-$l^{5}-phosphane Chemical compound [O-]P([O-])(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-L 0.000 title 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 239000011230 binding agent Substances 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 241000607479 Yersinia pestis Species 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 abstract description 7
- 241001674044 Blattodea Species 0.000 abstract description 2
- 241000254173 Coleoptera Species 0.000 abstract description 2
- 241000255925 Diptera Species 0.000 abstract description 2
- 241000238876 Acari Species 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- NQRYGPXAYYDKJB-UHFFFAOYSA-N phenyl hydrogen phosphonate Chemical class OP(=O)OC1=CC=CC=C1 NQRYGPXAYYDKJB-UHFFFAOYSA-N 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- HWWKEEKUMAZJLL-UHFFFAOYSA-N 4-bromo-2,5-dichlorophenol Chemical compound OC1=CC(Cl)=C(Br)C=C1Cl HWWKEEKUMAZJLL-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-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
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- CXDBXTHJTZQPOJ-UHFFFAOYSA-M [Na+].CC=C.CC=C.CC=C.CC=C.[O-]S(=O)(=O)C1=CC=CC=C1 Chemical compound [Na+].CC=C.CC=C.CC=C.CC=C.[O-]S(=O)(=O)C1=CC=CC=C1 CXDBXTHJTZQPOJ-UHFFFAOYSA-M 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- CJZYIPIKCPFBSG-UHFFFAOYSA-N chloro(phenyl)phosphinic acid Chemical compound OP(Cl)(=O)C1=CC=CC=C1 CJZYIPIKCPFBSG-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- IBDMRHDXAQZJAP-UHFFFAOYSA-N dichlorophosphorylbenzene Chemical compound ClP(Cl)(=O)C1=CC=CC=C1 IBDMRHDXAQZJAP-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002355 dual-layer Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000009472 formulation Methods 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
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent 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
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4084—Esters with hydroxyaryl compounds
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)
Abstract
Description
Phenylphosphonsäureester Die Erfindung betrifft Phenylphosphonsäureester der Formel Verfahren Zu ihrer Herstellung und ihre Verwendung als Wirkstoffe in Schädlingsbekämpfungsmitteln in er Formel 1 und im folgenden haben die Substituenten R, X und Y nachstehende Bedeutungen: R ist ein Alkylrest mit 1 bis 3 Kohlenstoffatomen, X steht für ein Chlor- oder Bromatom, Y für ein Brom- oder Jodatom.Phenylphosphonic acid esters The invention relates to phenylphosphonic acid esters of the formula Process For their preparation and their use as active ingredients in pesticides in formula 1 and below, the substituents R, X and Y have the following meanings: R is an alkyl radical having 1 to 3 carbon atoms, X is a chlorine or bromine atom, Y is a bromine or iodine atom.
Die Verbindungen der Formel I erhält man nach üblichen Verfahren: 1. Man setzt ein Phenol der Formel in Form eines Salzes, vorzugsweise eines Alkalisalzes, oder in Gegenwart eines säurebidenden Mittels, z.B. einer tertiären organischen Base wie Triäthylamin, mit einem 0-Alkylphenylphosphonsäurechlorid der Formel um. Als Reaktionsmedium dienen Lösungsmittel wie Methyläthylketon, Dioxan, Tetrahydrofuran, Benzol und Tetrachlorkohlenstoff. Die Reaktionstemperatur beträgt vorzugsweise etwa 10 -80°C, man kann aber auch bei anderen Temperaturen zwischen schmelzpunkt und Siedepunkt des Gemischs arbeiten.The compounds of the formula I are obtained by customary processes: 1. A phenol of the formula is used in the form of a salt, preferably an alkali salt, or in the presence of an acid-binding agent, for example a tertiary organic base such as triethylamine, with an 0-alkylphenylphosphonic acid chloride of the formula around. Solvents such as methyl ethyl ketone, dioxane, tetrahydrofuran, benzene and carbon tetrachloride are used as the reaction medium. The reaction temperature is preferably about 10 -80 ° C, but you can also work at other temperatures between the melting point and boiling point of the mixture.
di 2. Ausgehend vom Phenylphosphonsäurechlorid stellt man zunächst durch Umsetzung mit einem Phenol der Formel II im Molverhältnis 1 : 1 die Verbindung der Formel her und setzt diese in Gegenwart einer Base mit einem Alkohol der Formel (v) um. aie e Reaktion kam in einem Überschuß des Alkohols oder in einem organischen Lösungsmittel erfolgen. Die Reaktionstemperatur beträgt vorzugsweise 10 bis 80°C, doch ist die Umsetzung auch bei anderen Temperaturen zwischen dem Schmelzpunkt und dem Siedepunkt t des Gemischs mögliche Die Umsetzung gemaß Verfahren 2 Kann auch, ausgehend vom Phenylphosphonsäuredichlorid, onne Isolierung der Zwischenprodukte der Formel IV durchgeführt werden Die neuen Verbindungen fallen in großer Reinheit als farblose Öle an. Sie erweisen sich im DUiinschichtchromatogramm als einheitlich. Als Laufmittel wurde eine Mischung von n-Hexan und Aceton im Verhältnis 4 : 1 oder 2 : 1 verwendet;,die erfindungsgemäßen Verbindungen sind im ultravioletten Licht als blaue Flecke sichtbar. Die Chromatogramme können mit einer verdünnten Kaliumpermanganatlösung entwickelt werden.di 2. Starting from the phenylphosphonic acid chloride, the compound of the formula is first prepared by reaction with a phenol of the formula II in a molar ratio of 1: 1 and reacts this in the presence of a base with an alcohol of the formula (v). A reaction occurred in an excess of the alcohol or in an organic solvent. The reaction temperature is preferably 10 to 80 ° C, but the reaction is also possible at other temperatures between the melting point and the boiling point of the mixture new compounds are obtained in great purity as colorless oils. They turn out to be uniform in the dual-layer chromatogram. A mixture of n-hexane and acetone in a ratio of 4: 1 or 2: 1 was used as the mobile phase; the compounds according to the invention are visible as blue spots in ultraviolet light. The chromatograms can be developed with a dilute potassium permanganate solution.
Die neuen Verbindungen sind insektizid und akarizid wirksam.The new compounds are insecticidal and acaricidal.
Sie können zB. zur Bekämpfung von Fliegen, Käfern, Schaben und Spinnmilben, insbesondere aber von Raupen verwendet werden. Die Anwendung erfolgt in Form der üblichen Zubereitungen, beispielsweise Suspensionen, Emulsionen, Streu- und Stäubemitteln oder im ULV-Yerfahren.You can for example. to control flies, beetles, cockroaches and spider mites, but especially used by caterpillars. The application is in the form of the customary preparations, for example suspensions, emulsions, scattering agents and dusts or in the ULV process.
Beispiele für die Formulierung sind nachstehend angegeben: Stäubemittel Zusammensetzung: 5 % Wirkstoff gemäß Formel I 94 % Talkum 1 % Methylcellulose Die Bestandteile werden zur Herstellung des Stäubemittels homogen-vermahlen.Examples of the formulation are given below: Dust Composition: 5% active ingredient according to formula I 94% talc 1% methyl cellulose Die Components are ground homogeneously to produce the dust.
Suspentionspulver Zusammensetzung: 50 % Wirkstoff gemäß- Formel 1 40 % Kaolin 9 % Dispergiermittel (z.3. Lignlnsulfonat) 1 % Netzmittel (z.B. Natriumtetrapropylenbenzolsulfonat) Die Bestandteile werden vermahlen und d.as Mittel für die Anwendung so in Wasser suspendiert, daß die Wirkstoffkonzentration etwa 0,01 bis 0,5 % beträgt.Suspension powder Composition: 50% active ingredient according to formula 1 40% kaolin 9% dispersant (e.g. 3rd lignin sulfonate) 1% wetting agent (e.g. sodium tetrapropylene benzene sulfonate) The ingredients are ground and the agent for use in water suspended so that the active ingredient concentration is about 0.01 to 0.5%.
Emulsion Zusammensetzung: 25 % Wirkstoff gemäß Formel 1 70 % Dimethylformamid (oder Aceton) 5 5' Emulgator (z.B. Nonylphenolpolyglykoläther) Die Bestandteile werden in üblicher Weise zu einem Konzentrat verarbeitet. Dieses wird zur Anwendung in gewünschter Weise mit Wasser verdünnt, z.B. zu einer 0,01 bis 0,1 $ igen Emulsion.Emulsion Composition: 25% active ingredient according to formula 1 70% dimethylformamide (or acetone) 5 5 'emulsifier (e.g. nonylphenol polyglycol ether) The ingredients are processed into a concentrate in the usual way. This becomes the application diluted in the desired manner with water, e.g. to a 0.01 to 0.1% emulsion.
Die Herstellung der Wirkstoffe ist in den folgenden Beispielen näher erläutert.The preparation of the active ingredients is detailed in the following examples explained.
Beispiel 1 0-Methyl-0-(2,5-dichlor-4-bromphenyl)-phenylphosphonat 60,5 g 2,5-Dichlor-4-bromphenol und 39,0 g 0-Methyl-phenylphosphonsäurechlorid werden in 15Q Volumenteilen Tetrachlorkohlenstoff vorgelegt.Example 1 0-Methyl-0- (2,5-dichloro-4-bromophenyl) -phenylphosphonate 60.5 g of 2,5-dichloro-4-bromophenol and 39.0 g of 0-methyl-phenylphosphonic acid chloride are used Submitted in 15Q parts by volume of carbon tetrachloride.
Bei einer Temperatur von 10-200 C tropft man langsam 25 g Triäthylamin zu und ruhrt einige Stunden weiter. Dann wäscht man di.e Salze mit Wasser aus, entfernt das noch vorhandene-Phenol mit verdünnter Natronlauge und dampft das Lösungsmittel ab. Als Rückstand erhält man die Titelverbindung; Ausbeute: 82,5 g, n20D 1,5911.At a temperature of 10-200 ° C., 25 g of triethylamine are slowly added dropwise closed and kept stirring for a few hours. The salts are then washed out with water and removed the phenol still present with dilute sodium hydroxide solution and the solvent evaporates away. The title compound is obtained as the residue; Yield: 82.5 g, n20D 1.5911.
Beispiel 2 0-Methyl-0-(2,5-dichlor-4-bromphenyl)-phenylphosphonat 97,5 g Phenylphosphonsäuredichlorid in 500 ml Toluol werden bei 10 - 200C langsam unter Rühren mit einer toluol. Lösung von 121 g 2,5-Dichlor-4-bromphenol und 50,5 g Triäthylamin versetzt. Man läßt das Reaktionsgemisch bei 200C ca. 30 Minuten nachreagieren und versetzt anschließend mit einer toluol. Lösung von 20 g Methanol und 50,5 g Triäthylamin.Example 2 0-Methyl-0- (2,5-dichloro-4-bromophenyl) -phenylphosphonate 97.5 g of phenylphosphonic acid dichloride in 500 ml of toluene are slow at 10-200C while stirring with a toluene. Solution of 121 g of 2,5-dichloro-4-bromophenol and 50.5 g triethylamine added. The reaction mixture is allowed to react further at 200 ° C. for about 30 minutes and then added a toluene. Solution of 20 g of methanol and 50.5 g Triethylamine.
Nach Ablauf der reaktion wird das entstandene Triäthylaminhydrochlorid abgesaugt, die organische Phase mit verdünnter Natronlauge gewaschen und mit Wasser ausgeschüttelt. Nach Abdestillieren des Lösungsmittels erhält man 170 g Titelverbindung, n20D 1,5911.After the reaction has ended, the resulting triethylamine hydrochloride is suctioned off, the organic phase washed with dilute sodium hydroxide solution and washed with water shaken out. After distilling off the solvent, 170 g of the title compound are obtained, n20D 1.5911.
Summenformel C13H10BrC1203P Analyse berechnet C: 39,40 H: 2,55 P:
7,83 gefunden C: 39,50 H: 2,58 P: 8,-00 Entsprechend den Beispielen 1 und 2 werden
folgende Verbindungen erhalten:
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691964921 DE1964921A1 (en) | 1969-12-24 | 1969-12-24 | Phenyl phosphonate pesticides with insecti- - cidal and acaricidal activity |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691964921 DE1964921A1 (en) | 1969-12-24 | 1969-12-24 | Phenyl phosphonate pesticides with insecti- - cidal and acaricidal activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1964921A1 true DE1964921A1 (en) | 1971-07-01 |
Family
ID=5754989
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691964921 Pending DE1964921A1 (en) | 1969-12-24 | 1969-12-24 | Phenyl phosphonate pesticides with insecti- - cidal and acaricidal activity |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1964921A1 (en) |
-
1969
- 1969-12-24 DE DE19691964921 patent/DE1964921A1/en active Pending
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