DE2532628A1 - Fluorine substd. carbamoylmethyl dithiophosphonates - useful as insecticides, acaricides and nematocides - Google Patents
Fluorine substd. carbamoylmethyl dithiophosphonates - useful as insecticides, acaricides and nematocidesInfo
- Publication number
- DE2532628A1 DE2532628A1 DE19752532628 DE2532628A DE2532628A1 DE 2532628 A1 DE2532628 A1 DE 2532628A1 DE 19752532628 DE19752532628 DE 19752532628 DE 2532628 A DE2532628 A DE 2532628A DE 2532628 A1 DE2532628 A1 DE 2532628A1
- Authority
- DE
- Germany
- Prior art keywords
- active ingredient
- fluorine
- compounds according
- formula
- acid esters
- 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
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- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- WUHVJSONZHSDFC-UHFFFAOYSA-N ethyl 2-chloro-2-fluoroacetate Chemical compound CCOC(=O)C(F)Cl WUHVJSONZHSDFC-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000020044 madeira Nutrition 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N methyl iso-propyl ketone Natural products CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material 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
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic 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
- C07F9/28—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
- C07F9/4075—Esters with hydroxyalkyl 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)
Abstract
Description
Fluorsubstituierte Carbaminylmethyldithioalkanphosphonsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide, Akarizide und Nematizide Die vorliegende Erfindung betrifft neue fluorsubstituierte Carbaminylmethyldithioalkanphosphonsäureester, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide, Akarizide und Nematizide. Fluorine-substituted carbaminylmethyldithioalkanephosphonic acid esters, Process for their production and their use as insecticides, acaricides and nematicides The present invention relates to new fluorine-substituted carbaminylmethyldithioalkanephosphonic acid esters, a process for their production and their use as insecticides, acaricides and nematicides.
Es ist bereits bekannt, daß Carbaminylmethyldithiophosphor-(phosphon)-säureester, z.B. O,O-Dimethyl-S-(N-methyl-carbaminylmethyl)-thionothiolphoaphor- und O-Äthyl-S-(N-methyl-carbaminylmethyl)-thionothiolithanphosphonsäureester, insektizide und akarizide Eigenschaften haben (vergleiche USA-Patentschrift 2.494.283 und Deutsche Auslegeschrift 1.137.ol3).It is already known that carbaminylmethyldithiophosphorus (phosphonic) acid esters, e.g. O, O-dimethyl-S- (N-methyl-carbaminylmethyl) -thionothiolphosphoric and O-ethyl-S- (N-methyl-carbaminylmethyl) -thionothiolithanphosphonic acid ester, have insecticidal and acaricidal properties (see U.S. Patent 2,494,283 and German Auslegeschrift 1.137.ol3).
Es wurde gefunden, daß die neuen fluorsubstituierten Carbaminylmethyldithioalkanphosphonsäureester der Formel in welcher R und R' PUr gleiche oder verschiedene Alkylreste lit 1 bis 6 Kohlenstoffatoien stehen, während R" und R"', die gleich oder verschieden sein können, Wasserstoff oder Alkyl sit 1 bis 4 Kohlenstoffatolen bedeuten, starke insektizide,akarizide und nematizide Eigenschaften besitzen.It has been found that the new fluorine-substituted carbaminylmethyldithioalkanephosphonic acid esters of the formula in which R and R 'PUr are identical or different alkyl radicals having 1 to 6 carbon atoms, while R "and R"', which can be identical or different, denote hydrogen or alkyl sit 1 to 4 carbon atoms, strong insecticidal, acaricidal and nematicidal properties own.
Die Verbindungen der Formel (I) liegen im allgemeinen in Form von Racematen vor.The compounds of formula (I) are generally in the form of Racemates before.
Weiterhin wurde gefunden, daß die neuen fluorsubstituierten Carbaminylmethyldithioalkanphosphonsäureester der Formel (I) erhalten werden, wenn man O-Alkyldithioalkanphosphonsäureester der Formel in welcher R und R' die oben angegebene Bedeutung haben und M fUr Wasserstoff, ein Alkali-, Erdalkali- bzw.It has also been found that the new fluorine-substituted carbaminylmethyldithioalkanephosphonic acid esters of the formula (I) are obtained if O-alkyldithioalkanephosphonic acid esters of the formula in which R and R 'have the meaning given above and M stands for hydrogen, an alkali, alkaline earth or
AmmoniumSquivalent steht, mit Fluoracetamid-Derivaten der Formel in welcher R" und R"' die oben angegebene Bedeutung haben und Hal für Halogen, insbesondere Chlor oder Brom, steht, gegebenenfalls in Gegenwart von Säureakzeptoren und gegebenenfalls in Anwesenheit von Lösungs- oder Verdünnungslitteln umsetzt.Ammonium equivalent with fluoroacetamide derivatives of the formula in which R "and R"'have the meaning given above and Hal represents halogen, in particular chlorine or bromine, optionally reacted in the presence of acid acceptors and optionally in the presence of solvents or diluents.
überraschenderweise zeigen die erfindungsgemäßen fluorsubstituierten Carbaminylmethyldithioalkanphosphonsäureester eine bessere insektizide, akarizide und nematizide Wirkung als die entsprechenden aus dem Stand der Technik vorbekannten Carbaminylmethyldithiophosphor(phosphon)-sAureester analoger Konstitution und gleicher Wirkungsrichtung. Die Produkte gemäß vorliegender Erfindung stellen somit eine echte Bereicherung der Technik dar.Surprisingly, the fluorine-substituted compounds according to the invention show Carbaminylmethyldithioalkanephosphonic acid ester a better insecticidal, acaricidal and nematicidal activity than the corresponding previously known from the prior art Carbaminylmethyldithiophosphorus (phosphonic) acid ester of analogous constitution and the same Direction of action. The products according to the present invention thus represent a real one Enrichment of technology.
Verwendet man beispielsweise das Kaliumuals des O-iao-Propyläthandithiophosphonsäureesters und Fluor-chlor-N-methylacetauid als Ausgangsmaterialien, so kann der Reaktionsablauf durch das folgende Formelschema wiedergegeben werden: Die zu verwendenden Ausgangsstoffe sind durch die Formeln (II) und (III) eindeutig allgemein definiert. Vorzugsweise stehen darin Jedoch R für geradkettiges oder verzweigtes Alkyl mit 1 bis 4, R' für geradkettiges oder verzweigtes Alkyl mit 1 bis 3 Kohlenstoffatomen, R n für Wasserstoff, Methyl und Äthyl und R"' für Methyl und Äthyl.If, for example, the potassium ual of the O-iao-propylethiophosphonic acid ester and fluorochloro-N-methylacetauide are used as starting materials, the course of the reaction can be represented by the following equation: The starting materials to be used are clearly and generally defined by the formulas (II) and (III). Preferably, however, R stands for straight-chain or branched alkyl with 1 to 4, R 'for straight-chain or branched alkyl with 1 to 3 carbon atoms, R n for hydrogen, methyl and ethyl and R "' for methyl and ethyl.
Die als Ausgangsstoffe zu verwendenden O-Alkyldithioalkanphosphonsäureester (11) sind aus der Literatur bekannt und nach allgemein üblichen Verfahren herstellbar (vergleiche z.B. Deutsche Auslegeschrift 1.101.417), ebenso wie die Fluoracetamid-Derivate (III), die z.B. durch Umsetzen von Aminen mit Fluorchloressigsäurealkylestern (Herstellung siehe Org. Syntheses Coll. Vol. IV, S. 423) gewonnen werden können.The O-alkyldithioalkanephosphonic acid esters to be used as starting materials (11) are known from the literature and can be produced by generally customary processes (compare e.g. German Auslegeschrift 1.101.417), as well as the fluoroacetamide derivatives (III), which e.g. by reacting amines with fluorochloroacetic acid alkyl esters (manufacture see Org. Syntheses Coll. Vol. IV, p. 423) can be obtained.
Als Beispiele für die O-Alkyldithioalkanphosphonsäureester (II) seien im einzelnen genannt: 0-Methyl-, 0-Äthyl-, O-n-Propyl-, O-iso-Propyl-, O-n-Butyl-, O-iso-Butyl-, O-sec.-Butyl-, O-tert.-Butylmethan- bzw. -äthan-, -n-propan-, -iso-propandithiophosphonsäureester und die entsprechenden Alkali-, Erdalkali- und Ammoniumsalze.Examples of the O-alkyldithioalkanephosphonic acid esters (II) are specifically mentioned: 0-methyl-, 0-ethyl-, O-n-propyl-, O-iso-propyl-, O-n-butyl-, O-iso-butyl, O-sec-butyl, O-tert-butyl methane or -ethane, -n-propane, -iso-propanedithiophosphonic acid ester and the corresponding alkali, alkaline earth and ammonium salts.
Als Beispiele für die verfahrensgemäß umzusetzenden Fluoracetamid-Derivate (III) seien im einzelnen genannt: N-Methyl-, N-Äthyl-, N,N-Dimethyl-, N,N-Diäthyl-fluorchloracetamid.As examples of the fluoroacetamide derivatives to be reacted according to the process (III) may be mentioned in detail: N-methyl-, N-ethyl-, N, N-dimethyl-, N, N-diethyl-fluorochloroacetamide.
Das Verfahren zur Herstellung der erfindungsgemäßen Verbindungen wird bevorzugt unter Mitverwendung geeigneter Lösungs-und Verdünnungsmittel durchgeführt. Als solche kommen praktisch alle inerten organischen Solventien infrage. Hierzu gehören insbesondere aliphatische und aromatische, gegebenenfalls chlorierte Kohlenwasserstoffe, wie Benzol, Toluol, Xylol, Benzin, Methylenchlorid, Chloroform, Tetrachlorkohlenstoff, Chlorbenzol, oder Äther, z.B. Diäthyl- und DibutylEther, Dioxan, ferner Ketone, beispielsweise Aceton, Methyläthyl-, Methylisopropyl- und Methylisobutylketon, außerdem Nitrile, wie Aceto- und Propionitril.The process for making the compounds of the invention is preferably carried out with the use of suitable solvents and diluents. Practically all inert organic solvents can be used as such. For this include in particular aliphatic and aromatic, optionally chlorinated hydrocarbons, such as benzene, toluene, xylene, Gasoline, methylene chloride, chloroform, Carbon tetrachloride, chlorobenzene, or ethers, e.g. diethyl and dibutyl ethers, Dioxane, also ketones, for example acetone, methylethyl, methylisopropyl and Methyl isobutyl ketone, as well as nitriles such as aceto- and propionitrile.
Als Saureakzeptoren können alle üblichen Säurebindemittel Verwendung finden. Besonders bewährt haben sich Alkalicarbonate und -alkoholate, wie Natrium- und Kaliumcarbonat, Natrium- und Kaliummethylat bzw. -äthylat, ferner aliphatische, aromatische oder heterocyclische Amine, beispielsweise Triäthylamin, Trimethylamin, Dimethylanilin, Dimethylbenzylamin und Pyridin.All customary acid binders can be used as acid acceptors Find. Alkali carbonates and alcoholates, such as sodium and potassium carbonate, sodium and potassium methylate or ethylate, also aliphatic, aromatic or heterocyclic amines, for example triethylamine, trimethylamine, Dimethylaniline, dimethylbenzylamine and pyridine.
Die Reaktionstemperatur kann innerhalb eines größeren Bereichs variiert werden. Im allgemeinen arbeitet man zwischen o und 12o0C, vorzugsweise bei 30 bis 6o0C.The reaction temperature can vary within a relatively wide range will. In general, the temperature is between 0 and 120 ° C., preferably at 30 to 6o0C.
Die Umsetzung läßt man gewöhnlich bei NormaldrucX ablaufen0 Zur Durchführung des Verfahrens setzt man die Ausgangsstoffe im allgemeinen im äquimolaren Verhältnis ein. Ein Überschuß der einen oder anderen Komponente bringt keine wesentlichen Vorteile. Vorzugsweise legt man die Phosphonsäureesterkomponente (II) in Salzform in einem der oben genannten Lösungsmittel vor und versetzt die Lösung mit dem Fluoracetamid-Derivat (III).The reaction is usually allowed to proceed at normal pressure In the process, the starting materials are generally set in an equimolar ratio a. An excess of one or the other component has no significant advantages. The phosphonic acid ester component (II) is preferably put in salt form in one the above-mentioned solvents and the solution is mixed with the fluoroacetamide derivative (III).
Nach beendeter Reaktion, die meist bei erhöhter Temperatur durchgeführt wird, fügt man ein organisches Lösungsmittel zu der Mischung und arbeitet die organische Phase in Ublicher Weise durch Waschen, Trocknen und "Andestillieren" auf.After the reaction has ended, which is usually carried out at an elevated temperature one adds an organic solvent to the mixture and works the organic Phase in the usual way by washing, drying and "partial distillation".
Die neuen Verbinduagen fallen in Form von Ölen an, die sich nicht unzersetzt destillieren lassen, Jedoch durch sogenanntes "kndestillieren", d. h. durch längeres Erhitzen unter vermindertem Druck auf mäßig erhöhte Temperaturen von den letzten flüchtigen Anteilen befreit und auf diese Weise gereinigt werden. Zu ihrer Charakterisierung dient der Brechungsindex.The new compounds are in the form of oils that are not Let it distill without decomposition, but by so-called "undistillieren", d. H. by prolonged heating under reduced Pressure on moderately increased Temperatures freed from the last volatile components and cleaned in this way will. The refractive index is used to characterize them.
Wie bereits mehrfach erwähnt, zeichnen sich die erfindungsgemäßen fluorsubstituierten Carbaminylmethyldithioalkanphosphonsäureester durch eine hervorragende insektizide, akarizide und nematizide Wirksamkeit aus. Sie wirken gegen Pflanzen-, Hygiene- und Vorratsschädlinge und besitzen bei geringer Phytotoxizität sowohl eine gute Wirkung gegen saugende als auch fressende Insekten und Milben.As already mentioned several times, the inventive fluorine-substituted carbaminylmethyldithioalkanephosphonic acid ester by an excellent insecticidal, acaricidal and nematicidal effectiveness. They work against plant, Hygiene and storage pests and have both a low phytotoxicity good effect against sucking and eating insects and mites.
Aus diesem Grunde können die erfindungsgemäßen Verbindungen mit Frfolg im Pflanzenschutz sowie auf dem Hygiene- und Vorratsschutzsektor als Schädlingsbekämpfungsmittel eingesetzt werden.For this reason, the compounds according to the invention can be used successfully in crop protection as well as in the hygiene and stored product protection sector as pesticides can be used.
Zu den saugenden Insekten gehören im wesentlichen Blattläuse (Aphidae) wie die grtine Pfirsichblattlaus (Myzus persicae), die schwarze Bohnen- (Doralis fabae), Hafer- (Rhopalosiphum padi), Erbsen- (Macrosiphum pisi) und Kartofellaus (Macrosiphum solanifolil), ferner die Johannisbeergallen- (Cryptomyzus korschelti), mehlige Apfel- (Sappaphis mali), mehlige Pflaumen-(Hyalopterus arundinis) und schwarze Kirschenblattlaus (Myzus cerasi), außerdem Schild- und Schmierläuse (Coccina), z.B. die Efeuschild- (Aspidiotus hederae) und Napfschildlaus (Lecanium hesperidum) sowie die Schmierlaus (Pseudococcus maritimus); Blasenfüße (Thysanoptera) wie Hercinothrips femoralis und Wanzen, beispielsweise die Rüben- (Piesma quadrata), Baumwoll-(Dysdercus intermedius), Bett- (Cimex lectularius), Raub-(Rhodnius prolixus) und Chagaswanze (Triatoma infestans), ferner Zikaden, wie Euscelis bilobatus und Nephotettix bipunctatus.The sucking insects mainly include aphids (Aphidae) like the green peach aphid (Myzus persicae), the black bean (Doralis fabae), oat (Rhopalosiphum padi), pea (Macrosiphum pisi) and potato lice (Macrosiphum solanifolil), also the currant gall (Cryptomyzus korschelti), floury apple (Sappaphis mali), floury plum (Hyalopterus arundinis) and black Cherry aphid (Myzus cerasi), also scale and mealybugs (Coccina), e.g. the ivy shield (Aspidiotus hederae) and cup scale (Lecanium hesperidum) as well the mealybug (Pseudococcus maritimus); Bladder feet (Thysanoptera) such as Hercinothrips femoralis and bed bugs, for example beetroot (Piesma quadrata), cotton (Dysdercus intermedius), bed bug (Cimex lectularius), predatory bug (Rhodnius prolixus) and Chagas bug (Triatoma infestans), also cicadas such as Euscelis bilobatus and Nephotettix bipunctatus.
Bei den beißenden Insekten wären vor allem zu nennen Schmetterlingsraupen (Lepidoptera) wie die Kohlschabe (Plutella maculipennis), der Schwammspinner (Lymantria dispar), Goldafter (Euproctis chrysorrhoea) und Ringelspinner (Malacosoma neustria), weiterhin die Kohl- (Mamestra brassicae) und die Saateule (Agrotis segetum), der große Kohlweißling (Pieris brassicae), kleine Frostspanner (Cheimatobia brumata), Eichenwickler (Tortrix viridana), der Heer- (Laphygma frugiperda) und aegyptische Baumwollwurm (Prodenia litura), ferner die Gespinst-(Hyponomeuta padella), Mehl- (Ephestit kühniella ) und große Wachsmotte (Galleria mellonella), Weiterhin zählen zu den beißenden Insekten Käfer (Coleoptera) z.B. Korn- (Sitophilus granarius = Calandra granaria), Kartoffel- (Leptinotarsa decemlineata), Ampfer- (Gastrophysa viridula), Meerrettichblatt- (Phaedon cochleariae), Rapsglanz-(Meligethes aeneus), Himbeer- (Byturus tomentosus), Speisebohnen- (Bruchidius = Acanthoscelides obtectus), Speck-(Dermestes frischij, Khapra- (Trogoderma granarium), rotbrauner Reismehl- (Tribolium castaneum), Mais- (Calandra oder Sitophilus zeamais), Brot- (Stegobium paniceum), gemeiner Mehl- (Tenebrio molitor) und Getreideplattkäfer (Oryzaephilus surinamensis), aber auch im Boden lebende Arten z. B. DrahtwUrmer (Agriotes spec.) und Engerlinge (Melolontha melolontha); Schaben wie die Deutsche (HIattella germanica), Amerikanische (Periplaneta americana), Madeira- (Leucophaea oder Rhyparobia maderae), Orientalische (Blatta orientalis), Riesen- (Blaberus giganteus) und schwarze Riesenschabe (Blaberus fuscus) sowie Henschoutedenia flexivitta; ferner Orthopteren z.B. das Heimchen (Gryllus domesticus); Termiten wie die Erdtermite (Reticulitermes flavipes) und Hymenopteren wie Ameisen, beispielsweise die Wiesenameise (Lasius niger).Among the biting insects, butterfly caterpillars should be mentioned above all (Lepidoptera) such as the cabbage moth (Plutella maculipennis), the gypsy moth (Lymantria dispar), golden afters (Euproctis chrysorrhoea) and ring moth (Malacosoma neustria), furthermore the cabbage (Mamestra brassicae) and the seed owl (Agrotis segetum), the large cabbage white butterfly (Pieris brassicae), small frostworm (Cheimatobia brumata), Oak moth (Tortrix viridana), the army (Laphygma frugiperda) and Egyptian Cotton worm (Prodenia litura), also the web (Hyponomeuta padella), flour (Ephestit kühniella) and large wax moth (Galleria mellonella), Farther are among the biting insects beetles (Coleoptera) e.g. corn (Sitophilus granarius = Calandra granaria), potato (Leptinotarsa decemlineata), dock (Gastrophysa viridula), horseradish leaf (Phaedon cochleariae), rapeseed (Meligethes aeneus), Raspberry (Byturus tomentosus), table bean (Bruchidius = Acanthoscelides obtectus), Bacon (Dermestes frischij, Khapra (Trogoderma granarium), red-brown rice flour (Tribolium castaneum), corn (Calandra or Sitophilus zeamais), bread (Stegobium paniceum), common meal beetle (Tenebrio molitor) and grain beetle (Oryzaephilus surinamensis), but also species living in the ground, e.g. B. Wireworms (Agriotes spec.) and white grubs (Melolontha melolontha); Cockroaches like the Germans (HIattella germanica), American (Periplaneta americana), Madeira (Leucophaea or Rhyparobia maderae), Oriental (Blatta orientalis), giant (Blaberus giganteus) and giant black cockroach (Blaberus fuscus) and Henschoutedenia flexivitta; also orthopteres e.g. the House crickets (Gryllus domesticus); Termites such as the terrestrial termites (Reticulitermes flavipes) and Hymenoptera such as ants, for example the meadow ant (Lasius niger).
Die Dipteren umfassen im wesentlichen Fliegen wie die Tau-(Drosophila melanogaster), Mittelmeerfrucht- (Ceratitis capitata), Stuben- (Musca domestica), kleine Stuben- (Fannia canicularis), Glanz- (Phormia regina) und Schmeißfliege (Calliphora erythrocephala) sowie den Wadenstecher (Stomoxys calcitrans); ferner NUcken, z.B. Stechmücken wie die Gelbfieber- (Aedes aegypti), Haus- (Culex pipiens) und Malariamcicke (Anopheles stephensi), Zu den Milben (Acari) zählen besonders die Spinnmilben (Tetranychidae) wie die Bohnen- (Tetranychus telarius = Tetranychus althaeae oder Tetranychus urticae) und die Obstbaumspinnmilbe (Paratetranychus pilosus = Panonychus ulmi), Gallmilben, z.B. die Johannisbeergailmilbe (Eriophyes ribis) und Tarsonemiden beispielsweise die Triebspitzenmilbe (Hemitarsonemus latus) und Cyclamenmilbe (Tarsonemus pallidus); schließlich Zecken wie die Lederzecke (Ornithodorus moubata).The Diptera essentially comprise flies like the Tau (Drosophila melanogaster), Mediterranean fruit (Ceratitis capitata), room (Musca domestica), small house fly (Fannia canicularis), gloss fly (Phormia regina) and blowfly (Calliphora erythrocephala) and the calf stick (Stomoxys calcitrans); furthermore NUcken, e.g. Mosquitoes such as the yellow fever (Aedes aegypti), house (Culex pipiens) and malarial mosquitoes (Anopheles stephensi), The mites (Acari) are especially those Spider mites (Tetranychidae) such as the bean (Tetranychus telarius = Tetranychus althaeae or Tetranychus urticae) and the fruit tree spider mite (Paratetranychus pilosus = Panonychus ulmi), gall mites, e.g. the currant gail mite (Eriophyes ribis) and tarsonemids, for example the shoot tip mite (Hemitarsonemus latus) and Cyclamen mite (Tarsonemus pallidus); finally ticks like the leather tick (Ornithodorus moubata).
Bei der Anwendung gegen Hygiene- und Vorratsschädlinge, besonders Fliegen und Sticken, zeichnen sich die Verfahrensprodukte außerdem durch eine hervorragende Residualwirkung auf Holz und Ton sowie eine gute Alkalistabilität auf gekälkten Unterlagen aus.When used against hygiene and storage pests, especially Flying and embroidery, the process products are also characterized by excellent Residual effect on wood and clay as well as good alkali stability on limed Documents from.
Die erfindungsgemäßen Wirkstoffe haben bei geringer Warmblütertoxizität starke nematizide Eigenschaften und können deshalb zur Bekämpfung von Nematoden, insbesondere phytopathogenen Nematoden verwendet werden. Dazu gehören im wesentlichen Blattnematoden (Arphelenchoides), wie das Chrysanthemumälchen (A. ritzemabosi), das Erdbeerälchen (A. fragariae), das Reisälchen (A. oryzae); Stengelnematoden (Ditylenchus), wie das Stockälchen (D. Dipsaci); Wurzelgallennematoden (Meloidogyne), wie M. arenaria und M. incognita; zystenbildende Nematoden (Heterodera), wie die Kartoffelnematode (H. rostochiensis), die Rübennematode (H. schachtii); sowie freilebende Wurzelnematoden z.B. der Gattungen Pratylenchus, Paratylenchus, Rotylenchus, Xiphinema und Radopholus.The active ingredients according to the invention have low toxicity to warm-blooded animals strong nematicidal properties and can therefore be used to combat nematodes, in particular phytopathogenic nematodes can be used. This essentially includes Leaf nematodes (Arphelenchoides), such as the chrysanthemum male (A. ritzemabosi), the strawberry elbow (A. fragariae), the rice elbow (A. oryzae); Stem nematodes (Ditylenchus), like the little stick (D. Dipsaci); Root knot nematodes (Meloidogyne) such as M. arenaria and M. incognita; cyst-forming nematodes (Heterodera), such as the potato nematode (H. rostochiensis), the beet nematode (H. schachtii); as well as free-living root nematodes e.g. of the genera Pratylenchus, Paratylenchus, Rotylenchus, Xiphinema and Radopholus.
Die erfindungsgemäßen Wirkstoffe können in die üblichen Formulierungen übergeführt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Pasten und Granulate. Diese werden in bekannter Weise hergestellt, z.B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln, unter Druck stehenden verflüssigten Gasen und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln. Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen infrage: Aromaten, wie Xylol, Toluol, Benzol oder Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chloräthylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, Alkohole, wie Butanol oder Glycol sowie deren Äther und Ester, Ketone, wie Aceton, Methyläthylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser; mit verflüssigten gasförmigen Streckmitteln oder Trägerstoffen sind solche Flüssigkeiten gemeint, welche bei normaler Temperatur und unter Normaldruck gasförmig sind, z.B. Aerosol-Treibgase, wie Halogenkohlenwasserstoffe, z.B. Freon; als feste Trägerstoffe: natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, M¢ntmorillonit oder Diatomeenerde und synthetische Gesteinsüiehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate; als Emulgier- und/oder schaumerzeugende Mittel: nichtionogene und anionische Emulgatoren, wie Polyoxyäthylen-Fettsäure-Ester, Polyoxyäthylen-Fettalkohol-Äther, z.B. Alkylaryl-polyglykol-äther, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiweißhydrolysate; als-Dispergiermittel: z.B. Lignin, Sulfitablaugen und Methylcellulose.The active compounds according to the invention can be used in the customary formulations such as solutions, emulsions, suspensions, powders, pastes and granulates. These are produced in a known manner, e.g. by mixing the active ingredients liquefied pressurized liquids with extenders, i.e. liquid solvents Gases and / or solid carriers, optionally using surface-active substances Agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents Means. In the case of using water as an extender, e.g. organic Solvents can be used as co-solvents. As a liquid solvent are essentially: aromatics, such as xylene, toluene, benzene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, Chlorethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. petroleum fractions, alcohols such as butanol or glycol and their Ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or Cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, as well as water; with liquefied gaseous extenders or carriers such liquids are meant which are at normal temperature and under normal pressure are gaseous, e.g., aerosol propellants such as halogenated hydrocarbons, e.g., freon; as solid carrier materials: natural rock flour, such as kaolins, clays, talc, Chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock soles, such as finely divided silica, aluminum oxide and silicates; as emulsifying and / or Foaming agents: non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, Polyoxyethylene fatty alcohol ethers, e.g. alkylaryl polyglycol ethers, alkyl sulfonates, Alkyl sulfates, aryl sulfonates and protein hydrolysates; as a dispersant: e.g. Lignin, sulphite waste liquors and methyl cellulose.
Die erfindungsgemäßen Wirkstoffe können in den Formulierungen in Mischung mit anderen- bekannten Wirkstoffen vorliegen.The active compounds according to the invention can be mixed in the formulations with other known active ingredients.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 land 95 Gewichtsprozent Wirkstoff, vorzugsweise zwischen 0,5 und 90 %.The formulations generally contain between 0.1 and 95 percent by weight Active ingredient, preferably between 0.5 and 90%.
Die Wirkstoffe können als solche, in Form ihrer Formulierungen oder in den daraus bereiteten Anwendungsformen, wie gebrauchsfertige Lösungen, Emulsionen, Schäume, Suspensionen, Pulver, Pasten, lösliche Pulver, Stäubmittel und Granulate angewendet werden. Die Anwendung geschieht in üblicher Weise, z.B. durch Verspritzen, Versprühen, Vernebeln, Verstäuben, Verstreuen, Verräuchern, Vergasen, Gießen, Beizen oder Inkrustieren.The active ingredients can be used as such, in the form of their formulations or in the application forms prepared therefrom, such as ready-to-use solutions, emulsions, Foams, suspensions, powders, pastes, soluble powders, dusts and granules be applied. It is used in the usual way, e.g. by spraying, Spraying, atomizing, dusting, scattering, smoking, gasifying, pouring, pickling or encrusting.
Die Wirkstoffkonzentrationen in den anwendungsfertigen Zubereitungen können in größeren Bereichen variiert werden. Im allgemeinen liegen sie zwischen 0,0001 und 10 46, vorzugsweise zwischen 0,01 und 1 %.The active ingredient concentrations in the ready-to-use preparations can be varied in larger areas. In general, they are between 0.0001 and 10 46, preferably between 0.01 and 1%.
Die Wirkstoffe können auch mit gutem Erfolg im Ultra-Low-Volume-Verfahren (ULV) verwendet werden, wo es möglich ist, Formulierungen bis zu 95 % oder sogar den 100 -igen Wirkstoff allein auszubringen.The active ingredients can also be used with good success in the ultra-low-volume process (ULV) used where possible, formulations up to 95% or even to apply the 100% active ingredient alone.
Beispiel A Grenzkonzentrations-Test / Bodeninsekten I Testinsekt: Phorbia antiqua-Maden im Boden Lösungsmittel: 3 Gewichtsteile Aceton Emulgator: 1 Gewichtsteil Alkylarylpolyglykoläther Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel, gibt die angegebene Menge Emulgator zu und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.Example A Limit Concentration Test / Soil Insect I Test Insect: Phorbia antiqua maggots in the soil Solvent: 3 parts by weight acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether for the production of an appropriate active ingredient preparation mixing 1 part by weight of active ingredient with the specified amount of solvent, add the specified amount of emulsifier and dilute the concentrate with water the desired concentration.
Die Wirkstoffzubereitung wird innig mit dem Boden vermischt.The active ingredient preparation is intimately mixed with the soil.
Dabei spielt die Konzentration des Wirkstoffs in der Zubereitung praktisch keine Rolle, entscheidend ist allein die Wirkstoffgewichtsmenge pro Volumeneinheit Boden, welche in ppm (= mg/l) angegeben wird. Man füllt den Boden in Töpfe und läßt diese bei Raumtemperatur stehen.The concentration of the active ingredient in the preparation plays a practical role Doesn't matter, the only decisive factor is the amount of active ingredient by weight per unit volume Soil, which is given in ppm (= mg / l). The bottom is filled into pots and left these stand at room temperature.
Nach 24 Stunden werden die Testtiere in den behandelten Boden gegeben und nach weiteren 2 bis 7 Tagen wird der Wirkungsgrad des Wirkstoffs durch Auszählen der toten und lebenden Testinsekten in 96 bestimmt. Der Wirkungsgrad ist 100 5', wenn alle Testinsekten abgetötet worden sind, er ist 0 96, wenn noch genau so viele Testinsekten leben wie bei der unbehandelten Kontrolle.After 24 hours, the test animals are placed in the treated soil and after another 2 to 7 days, the effectiveness of the active ingredient is determined by counting of the dead and live test insects determined in 96. The efficiency is 100 5 ', when all test insects have been killed, it is 0 96, if just as many Test insects live as in the untreated control.
Wirkstoffe, Aufwandmengen und Resultate gehen aus der nachfolgenden
Tabelle 1 hervor:
Tabelle 1 Grenzkonzentrations-Test / Bodeninsekten
I (Phorbia antiqua-Maden im Boden)
Die Wirkstoffzubereitung wird innig mit dem Boden vermischt.The active ingredient preparation is intimately mixed with the soil.
Dabei spielt die Konzentration des Wirkstoffs in der Zubereitung praktisch keine Rolle, entscheidend ist allein die Wirkstoffgewichtsmenge pro Volumeneinheit Boden, welche in ppm (= mg/l) angegeben wird. Man füllt den Boden in Töpfe und läßt diese bei Raumtemperatur stehen.The concentration of the active ingredient in the preparation plays a practical role Doesn't matter, the only decisive factor is the amount of active ingredient by weight per unit volume Soil, which is given in ppm (= mg / l). The bottom is filled into pots and left these stand at room temperature.
Nach 24 Stunden werden die Testtiere in den behandelten Boden gegeben und nach weiteren 2 bis 7 Tagen wird der Wirkungsgrad des Wirkstoffs durch Auszählen der toten und lebenden Testinsekten in,' bestimmt. Der Wirkungsgrad ist 100 5', wenn alle Testinsekten abgetötet worden sind, er ist 0 5', wenn noch genau so viele Testinsekten leben wie bei der unbehandelten Kontrolle.After 24 hours, the test animals are placed in the treated soil and after another 2 to 7 days, the effectiveness of the active ingredient is determined by counting of the dead and living test insects in, 'intended. The efficiency is 100 5 ', when all test insects have been killed, it is 0 5 ', if just as many Test insects live as in the untreated control.
Wirkstoffe, Aufwandmengen und Resultate gehen aus der nachfolgenden
Tabelle 2 hervor:
Tabelle 2 Grenzkonzentrations-Test / Bodeninsekten
II (Tenebrio molitor-Larven im Boden)
Die Wirkstoffzubereitung wird innig mit Boden vermischt, der mit den Testnematoden stark verseucht ist. Dabei spielt die Konzentration des Wirkstoffs in der Zubereitung praktisch keine Rolle, entscheidend ist allein die Wirkstoffmenge pro Volumeneinheit Boden, welche in ppm angegeben wird. Man füllt den behandelten Boden in Töpfe, sät Salat ein und hält die Töpfe bei einer Gewächshaus-Temperatur von 27 0C.The active ingredient preparation is intimately mixed with the soil with the Test nematode is heavily contaminated. The concentration of the active ingredient plays a role here Practically no role in the preparation, the only decisive factor is the amount of active ingredient per unit volume of soil, which is given in ppm. One fills the treated one Ground in pots, sow lettuce and keep the pots at a greenhouse temperature from 27 0C.
Nach vier Wochen werden die Salatwurzeln auf Nematodenbefall (Wurzelgallen) untersucht und der Wirkungsgrad des Wirkstoffs in % bestimmt. Der Wirkungsgrad ist 100 5', wenn der Befall vollständig vermieden wird, er ist 0 5', wenn der Befall genau so hoch ist wie bei den Kontrollpflanzen in unbehandeltem, aber in gleicher Weise verseuchtem Boden.After four weeks, the lettuce roots are checked for nematode infestation (root galls) investigated and determined the efficiency of the active ingredient in%. The efficiency is 100 5 'if the infestation is completely avoided, it is 0 5' if the infestation is exactly as high as in the control plants in untreated, but the same Way contaminated soil.
Wirkstoffe, Aufwandmengen und Resultate gehen aus der nachfolgenden
Tabelle 3 hervor:
Tabelle 3 Grenzkonzentrations-Test / Nematoden
(Moloidogyne incognita)
Mit der Wirkstoffzubereitung besprüht man Kohlblätter (Brassica oleracea) taufeucht und besetzt sie mit Raupen der Kohlschabe (Plutella maculipennis).Cabbage leaves (Brassica oleracea) are sprayed with the preparation of the active compound dewy and populated with caterpillars of the cabbage moth (Plutella maculipennis).
Nach den angegebenen Zeiten wird die Abtötung in % bestimmt.After the specified times, the destruction is determined in%.
Dabei bedeutet 100 5', daß alle Raupen abgetötet wurden; 0 % bedeutet, daß keine Raupen abgetötet wurden.100 5 'means that all the caterpillars have been killed; 0% means that no caterpillars were killed.
Wirkstoffe, Wirkstoffkonzentrationen, Auswertungszeiten und Resultate
gehen aus der nachfolgenden Tabelle 4 hervor:
T a b e l l e 4 (Plutella-Test)
Mit der Wirkstoffzubereitung werden Bohnenpflanzen (Phaseolus vulgaris), die stark von allen Entwicklungsstadien der gemeinen Spinnmilbe oder Bohnenspinnmilbe (Tetranychus urticae) befallen sind, tropfnaß besprüht.Bean plants (Phaseolus vulgaris), which strongly differ from all stages of development of the common spider mite or bean spider mite (Tetranychus urticae) are infected, sprayed dripping wet.
Nach den angegebenen Zeiten wird die Abtötung in 96 bestimmt.After the specified times, the destruction in 96 is determined.
Dabei bedeutet 100 5', daß alle Spinnmilben abgetötet wurden; 0 96 bedeutet, daß keine Spinnmilben abgetötet wurden.100 5 'means that all spider mites have been killed; 0 96 means that no spider mites have been killed.
Wirkstoffe, Wirkstoffkonzentrationen, Auswertungszeiten und Resultate
gehen aus der nachfolgenden Tabelle 5 hervor:
Tabelle 5 (Tetranychus-Test)
In analoger Weise können die folgenden Verbindungen hergestellt werden:
Zu 45 g einer wässrigen (4c bis 5o5'ig; entsprechend o,4 bis 0,5 Mol) Dimethylaminlösung fügt man bei 50C 42 g (o,3 Mol) Fluorchloressigsäureäthylester (hergestellt nach Org.To 45 g of an aqueous (4c to 50%; corresponding to 0.4 to 0.5 mol) Dimethylamine solution is added at 50 ° C. 42 g (0.3 mol) of ethyl fluorochloroacetate (manufactured according to Org.
Syntheses Coll. Vol. IV, S. 423) und rührt das Gemisch 4 Stunden bei O bis 5°C. Anschließend zieht man bei maximal 40°C Badtemperatur das Wasser ab, destilliert den Rückstand unter vermindertem Druck und erhält so 20 g (47 96 der Theorie) Fluor-chlor-N,N-dimethylacetamid in Form einer farblosen Flüssigkeit mit dem Siedepunkt 53 0C / 0,01 Torr und dem Brechungsindex nD24: 1,4530.Syntheses Coll. Vol. IV, p. 423) and the mixture is stirred for 4 hours 0 to 5 ° C. The water is then drawn off at a maximum bath temperature of 40 ° C, the residue is distilled under reduced pressure and thus receives 20 g (47 96 der Theory) Fluoro-chloro-N, N-dimethylacetamide in the form of a colorless liquid with the boiling point 53 0C / 0.01 Torr and the refractive index nD24: 1.4530.
In gleicher Weise können die folgenden Verbindungen erhalten werden: Siedepunkt 51OC/O 01 Torr; Brechungsindex n D: 1,4444 Siedepunkt 65-68°C/0,1 Torr; Schmelzpunkt: 320CIn the same way, the following compounds can be obtained: Boiling point 51OC / O 01 Torr; Refractive index n D: 1.4444 boiling point 65-68 ° C / 0.1 Torr; Melting point: 320C
Claims (6)
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0353574A1 (en) * | 1988-08-04 | 1990-02-07 | Bayer Ag | S-(haloalkyl)-dithiophosphoric(phosphonic) acid esters, process for their preparation and their use for combatting pests |
EP0417558A2 (en) * | 1989-09-12 | 1991-03-20 | Bayer Ag | S-haloalkyl(di)(tri)(thio)phosphoric(phosphonic)acid(amide) esters |
-
1975
- 1975-07-22 DE DE19752532628 patent/DE2532628A1/en active Pending
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0353574A1 (en) * | 1988-08-04 | 1990-02-07 | Bayer Ag | S-(haloalkyl)-dithiophosphoric(phosphonic) acid esters, process for their preparation and their use for combatting pests |
EP0417558A2 (en) * | 1989-09-12 | 1991-03-20 | Bayer Ag | S-haloalkyl(di)(tri)(thio)phosphoric(phosphonic)acid(amide) esters |
EP0417558A3 (en) * | 1989-09-12 | 1992-06-03 | Bayer Ag | S-haloalkyl(di)(tri)(thio)phosphoric(phosphonic)acid(amide) esters |
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