CH627476A5 - Pesticide - Google Patents
Pesticide Download PDFInfo
- Publication number
- CH627476A5 CH627476A5 CH198477A CH198477A CH627476A5 CH 627476 A5 CH627476 A5 CH 627476A5 CH 198477 A CH198477 A CH 198477A CH 198477 A CH198477 A CH 198477A CH 627476 A5 CH627476 A5 CH 627476A5
- Authority
- CH
- Switzerland
- Prior art keywords
- carbon atoms
- radical
- dichloro
- formula
- cyanophenyl
- Prior art date
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- 239000000575 pesticide Substances 0.000 title claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- LIDUSYSXQFAHHK-UHFFFAOYSA-N 2,5-dichloro-4-hydroxybenzonitrile Chemical compound OC1=CC(Cl)=C(C#N)C=C1Cl LIDUSYSXQFAHHK-UHFFFAOYSA-N 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 150000004707 phenolate Chemical class 0.000 claims description 3
- 241000607479 Yersinia pestis Species 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 229940031826 phenolate Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- -1 2,5-dichloro-4-cyanophenyl Chemical group 0.000 description 8
- 229910019142 PO4 Inorganic materials 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 6
- 239000010452 phosphate Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 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 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000238660 Blattidae Species 0.000 description 1
- GJPYESGAIZJIGC-UHFFFAOYSA-N C(C)(C)[ClH]P(=S)(C)Cl Chemical compound C(C)(C)[ClH]P(=S)(C)Cl GJPYESGAIZJIGC-UHFFFAOYSA-N 0.000 description 1
- QXHSLSJFHFRLTN-UHFFFAOYSA-N C(C)[ClH]P(=S)(C1=CC=CC=C1)Cl Chemical compound C(C)[ClH]P(=S)(C1=CC=CC=C1)Cl QXHSLSJFHFRLTN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 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
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
-
- 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
- A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
- A01N57/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34 containing aromatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—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)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Die Erfindung betrifft ein Schädlingsbekämpfungsmittel, enthaltend einen Thiono- bzw. Thionothiolphosphor- sowie Thionophosphonsäureester der Formel I The invention relates to a pesticide containing a thionophosphorus or thionophiol acid and thionophosphonic acid ester of the formula I.
5R1° 5R1 °
R, R,
0 0
10 10th
CN (I); CN (I);
die Verwendung der Verbindung zur Schädlingsbekämpfung und 15 Verfahren zu ihrer Herstellung. the use of the pest control compound and 15 methods of making it.
In der Formel I und im folgenden haben die Substituenten Rj und R2 die nachstehende Bedeutung: In Formula I and below, the substituents Rj and R2 have the following meanings:
R] bedeutet einen Alkylrest mit 1 bis 3 Kohlenstoffatomen; R2 bezeichnet einen Alkylrest mit 1 bis 3 Kohlenstoffatomen, einen Phenylrest, einen Alkoxyrest mit 1 bis 3 Kohlenstoffatomen oder einen Alkylthiorest mit 1 bis 4 Kohlenstoffatomen. R] represents an alkyl radical having 1 to 3 carbon atoms; R2 denotes an alkyl radical with 1 to 3 carbon atoms, a phenyl radical, an alkoxy radical with 1 to 3 carbon atoms or an alkylthio radical with 1 to 4 carbon atoms.
Hervorzuheben sind diejenigen Verbindungen der Formel I, in denen die Alkyl-, Alkoxy- und Alkylmercaptogruppen 1 bis 2 C-Atome enthalten. To be emphasized are those compounds of formula I in which the alkyl, alkoxy and alkyl mercapto groups contain 1 to 2 carbon atoms.
Die Verbindungen der Formel I erhält man nach üblichen Methoden durch Umsetzung eines Phosphorsäurechlorids der Formel The compounds of formula I are obtained by customary methods by reacting a phosphoric acid chloride of the formula
20 20th
25 25th
30 30th
CN (I), CN (I),
50 50
55 55
60 60
Ri0>. Ri0>.
P P
^C1 ^ C1
(II) (II)
35 35
mit 2,5-Dichlor-4-cyanophenol with 2,5-dichloro-4-cyanophenol
Cl Cl
40 40
45 45
in Form eines Phenolats oder in Gegenwart eines säurebindenden Mittels. in the form of a phenolate or in the presence of an acid-binding agent.
Die Umsetzung erfolgt vorteilhaft in einem geeigneten organischen Lösungsmittel, z. B. Toluol, Dioxan, Tetrahydrofuran, Methyläthylketon, oder auch in Wasser bei Temperaturen von etwa 30 bis 90° C. Die geeigneten Phenolate können sich z.B. von Alkalibasen oder von organischen Basen, wie Triäthylamin, Äthylpiperidin, Trimethylamin, ableiten. The reaction is advantageously carried out in a suitable organic solvent, e.g. B. toluene, dioxane, tetrahydrofuran, methyl ethyl ketone, or also in water at temperatures of about 30 to 90 ° C. The suitable phenolates can e.g. derived from alkali bases or from organic bases such as triethylamine, ethylpiperidine, trimethylamine.
Die rohen Ester werden in der Regel zur Reinigung in einem geeigneten organischen Lösungsmittel aufgenommen und die Lösung mit verdünnter Natronlauge und Wasser gewaschen, getrocknet und gegebenenfalls mit Aktivkohle behandet und eingeengt. The crude esters are generally taken up for cleaning in a suitable organic solvent and the solution is washed with dilute sodium hydroxide solution and water, dried and, if appropriate, treated with activated carbon and concentrated.
Die neuen Verbindungen bleiben als farblose bis hellgelbe Öle von genügender Reinheit zurück. Teilweise sind die Ester kristallin. Im allgemeinen sind die Verbindungen im Hochvakuum ohne merkliche Zersetzung destillierbar. The new compounds remain as colorless to light yellow oils of sufficient purity. Some of the esters are crystalline. In general, the compounds can be distilled in a high vacuum without noticeable decomposition.
Soweit die Ausgangsstoffe noch nicht beschrieben wurden, 65 können sie nach an sich bekannten Verfahren gewonnen werden. - Die Ester der Formel I können als Wirkstoffe in Schädlingsbekämpfungsmitteln verwendet werden, sie wirken stark insektizid und akarizid, beispielsweise auch gegen resistente Spinnmilben, Insofar as the starting materials have not yet been described, 65 they can be obtained by processes known per se. - The esters of formula I can be used as active ingredients in pesticides, they have a strong insecticidal and acaricidal action, for example also against resistant spider mites,
3 3rd
627 476 627 476
ausserdem haben sie eine fungizide Wirkung, insbesondere gegen echten Mehltau. they also have a fungicidal effect, especially against powdery mildew.
Die gute Wirksamkeit der neuen Verbindungen zeigt sich z. B. beim Vergleich zwischen dem Handelsprodukt The good effectiveness of the new compounds is shown, for. B. when comparing the commercial product
0,0-Diäthyl-0-(4-brom-2,5-dichlorphenyl)-thionophosphat 0.0-diethyl 0- (4-bromo-2,5-dichlorophenyl) thionophosphate
(A) und der erfindungsgemässen Verbindung 0,0-Diäthyl-0-(2,5-dichlor-4-cyanophenyl)-thionophosphat (A) and the compound 0.0-diethyl-0- (2,5-dichloro-4-cyanophenyl) thionophosphate according to the invention
(B) (B)
an orientalischen Schaben (Kontrolle nach 2 Tagen, Abtö-tung in %): on oriental cockroaches (control after 2 days, mortality in%):
Wirkstoff 0,6 ppm 1,0 ppm 2,5 ppm Active ingredient 0.6 ppm 1.0 ppm 2.5 ppm
A 0 10 30 A 0 10 30
B 60 90 100 B 60 90 100
Für die Anwendung werden Verbindungen der Formel I zu den üblichen Formulierungen verarbeitet, z. B. zu Emulsionen, Suspensionen, Streu-und Stäubemitteln. Die Anwendungskonzentrationen liegen im allgemeinen zwischen etwa 0,01 und 5 Gew.-%. Sie können jedoch auch höher gewählt werden, z. B. für die Anwendung der Wirkstoffe in ULV-Formulierungen, die bis zu etwa 90 Gew.-% Wirkstoff enthalten können. For use, compounds of the formula I are processed to give the customary formulations, e.g. B. to emulsions, suspensions, scattering and dusting agents. The application concentrations are generally between about 0.01 and 5% by weight. However, they can also be chosen higher, e.g. B. for the use of active ingredients in ULV formulations, which can contain up to about 90 wt .-% active ingredient.
Formulierungsbeispiele a) Emulsionskonzentrate 20 Gew.-Teile eines Wirkstoffs gemäss der Erfindung werden in 75 Gew.-Teilen Xylol gelöst und mit 5 Gew.-TeilenNonylphe-nolpolyglycoläther versetzt. Diese Lösung wird für die Anwendung mit Wasser emulgiert. Der Wirkstoffgehalt der Emulsionen beträgt im allgemeinen zwischen 0,01 und 0,1 Gew.-%. 30 Formulation examples a) Emulsion concentrates 20 parts by weight of an active ingredient according to the invention are dissolved in 75 parts by weight of xylene and 5 parts by weight of nonylphenol polyglycol ether are added. This solution is emulsified with water for use. The active substance content of the emulsions is generally between 0.01 and 0.1% by weight. 30th
b) Stäubemittel b) dusts
2 Gew.-Teile 0,0-Diäthyl-0-(2,5-dichlor-4-cyanophenyl)-thionophat werden auf 98 Gew.-Teile Kaolin aufgedüst und mit diesem homogen vermählen. 2 parts by weight of 0.0-diethyl-0- (2,5-dichloro-4-cyanophenyl) thionophate are sprayed onto 98 parts by weight of kaolin and mixed homogeneously with it.
c) Suspensionspulver 35 25 Gew.-Teile eines erfindungsgemässen Wirkstoffs werden auf 73 Gew.-Teile Kieselgur aufgedüst und nach Zusatz von 2 Teilen Natrium-naphthalinsulfonat homogen vermählen. Für die Anwendung wird das erhaltene Suspensionspulver mit Wasser bis zur gewünschten Konzentration (vorzugsweise 0,01—0,1 40 Gew.-% Wirkstoff) vermischt. c) suspension powder 35 25 parts by weight of an active ingredient according to the invention are sprayed onto 73 parts by weight of diatomaceous earth and, after addition of 2 parts of sodium naphthalenesulfonate, homogeneously ground. For use, the suspension powder obtained is mixed with water to the desired concentration (preferably 0.01-0.1 40% by weight of active ingredient).
Die Herstellung der Verbindungen der Formel I ist in den folgenden Beispielen näher erläutert. The preparation of the compounds of the formula I is explained in more detail in the following examples.
(0,75 Mol) 15%igerwässriger Natronlauge gelöst, mit 150 ml Dichloräthan versetzt und bei einer Temperatur von 60—65° C unter kräftigem Rühren mit 170 g 0,0-Diäthyl-thionophosphor-säurechlorid umgesetzt. Nach etwa 1,5 Stunden ist die Reaktion 5 beendet. Die organische Phase wird abgetrennt und mit 1 n Natronlauge und Wasser gewaschen. Nach dem Abdestillieren des Lösungsmittels wird das überschüssige Phosphorsäurechlorid bei ca. 1 Torr abgezogen. (0.75 mol) 15% aqueous sodium hydroxide solution dissolved, mixed with 150 ml dichloroethane and reacted at a temperature of 60-65 ° C with vigorous stirring with 170 g of 0.0-diethyl-thionophosphoric acid chloride. Reaction 5 is complete after about 1.5 hours. The organic phase is separated off and washed with 1N sodium hydroxide solution and water. After the solvent has been distilled off, the excess phosphoric acid chloride is drawn off at about 1 torr.
Die Ausbeute beträgt 228 g (96% d. Th.). The yield is 228 g (96% of theory).
io Die Verbindung wird entsprechend Beispiel 1 zur Kristallisation gebracht, Fp. 58°C. io The compound is brought to crystallization according to Example 1, mp. 58 ° C.
Beispiel 3 Example 3
15 0,0-Dimethyl-0-(2,5-dichlor-4-cyanophenyl)-thionophosphat 15 0.0-Dimethyl-0- (2,5-dichloro-4-cyanophenyl) thionophosphate
Die Verbindung wird entsprechend Beispiel 1 oder Beispiel 2 aus 0,0-Dimethyl-thionophosphorsäurechlorid und 2,5-Dichlor-4-cyanophenol hergestellt. The compound is prepared according to Example 1 or Example 2 from 0.0-dimethyl-thionophosphoric chloride and 2,5-dichloro-4-cyanophenol.
20 Brechungsindex: n2o 1,6032; Ausbeute: 82% d. Th. 20 refractive index: n2o 1.6032; Yield: 82% of theory Th.
Beispiel 4 Example 4
0,0-Di-n-propyl-0-(2,5-dichlor-4-cyanophenyl)-thionophosphat 0.0-di-n-propyl-0- (2,5-dichloro-4-cyanophenyl) thionophosphate
25 25th
45 45
Beispiel 1 example 1
0,0-Diäthyl-0-(2,5-dichlor-4-cyanophenyl)-thionophosphat 0,0-diethyl-0- (2,5-dichloro-4-cyanophenyl) thionophosphate
18,8 g 2,5-Dichlor-4-cyanophenol werden in 100 ml Tetrahy-drofuran gelöst und mit 14,0 g Kaliumcarbonat versetzt. Hierbei 50 bildet sich das Kaliumsalz des Phenols. Unter Rühren wird bei 50 - 60° C langsam 0,0-Diäthyl-thionophosphorsäurechlorid eingetropft und anschliessend 3 Stunden im Wasserbad unter Rück-fluss erhitzt. Die Reaktionslösung wird filtriert und eingeengt. Der Rückstand wird in 1,2-Dichloräthan gelöst und mit verdünn- 55 ter Natronlauge ausgeschüttelt. Nach dem Trocknen der Dichlor- 18.8 g of 2,5-dichloro-4-cyanophenol are dissolved in 100 ml of tetrahydrofuran and mixed with 14.0 g of potassium carbonate. The potassium salt of the phenol forms here. While stirring, 0.0-diethyl-thionophosphoric acid chloride is slowly added dropwise at 50-60 ° C. and then heated under reflux in a water bath for 3 hours. The reaction solution is filtered and concentrated. The residue is dissolved in 1,2-dichloroethane and shaken out with dilute sodium hydroxide solution. After drying the dichloro-
äthanlösung mit Natriumsulfat wird filtriert und das Lösungsmittel im Vakuum vollständig entfernt. Ethane solution with sodium sulfate is filtered and the solvent is completely removed in vacuo.
Ausbeute 33,5 g (98,5% d. Th.). 60 Yield 33.5 g (98.5% of theory). 60
Die Substanz ist dünnschichtchromatographisch einheitlich. Aus einer Mischung von Cyclohexan und Methanol kann die Verbindung kristallin erhalten werden; Fp 58° C. The substance is uniform by thin layer chromatography. The compound can be obtained in crystalline form from a mixture of cyclohexane and methanol; Mp 58 ° C.
Analog Beispiel 1 wird durch Umsetzung von 0,0-Di-n-propyl-thionophosphorsäurechlorid mit 2,5-Dichlor-4-cy ano-phenol die Titelverbindung hergestellt. Analogously to Example 1, the title compound is prepared by reacting 0.0-di-n-propyl-thionophosphoric chloride with 2,5-dichloro-4-cy ano-phenol.
Brechungsindex: n2o 1,5834; Ausbeute 81% d. Th. Refractive index: n2o 1.5834; Yield 81% of theory Th.
Beispiel 5 Example 5
0-Äthyl-0-(2,5-dichlor-4-cyanophenyl)-äthylthionophosphonat 0-ethyl-0- (2,5-dichloro-4-cyanophenyl) ethylthionophosphonate
Die Titelverbindung wird entsprechend Beispiel 1 oder Beispiel 2 aus 2,5-Dichlor-4-cyanophenol und O-Äthyl-äthyl-thio-nophosphonsäurechlorid hergestellt. The title compound is prepared in accordance with Example 1 or Example 2 from 2,5-dichloro-4-cyanophenol and O-ethyl-ethyl-thio-nophosphonic acid chloride.
Brechungsindex: n2o 1,5983; Ausbeute 74% d. Th. Refractive index: n2o 1.5983; Yield 74% of theory Th.
Beispiel 6 Example 6
0-Isopropyl-0-(2,5-dichlor-4-cyanophenyl)-methylthionophos-phonat 0-isopropyl-0- (2,5-dichloro-4-cyanophenyl) methylthionophosphonate
Analog Beispiel 1 oder Beispiel 2 erhält man aus 2,5-Dichlor-4-cyanophenol und O-Isopropyl-methylthionophosphonsäure-chlorid die Titelverbindung. Analogously to Example 1 or Example 2, the title compound is obtained from 2,5-dichloro-4-cyanophenol and O-isopropyl-methylthionophosphonic acid chloride.
Brechungsindex: n2o 1,6023; Ausbeute 78% d. Th. Refractive index: n2o 1.6023; Yield 78% of theory Th.
Beispiel 7 Example 7
0-Äthyxl-0-(2,5-dichlor-4-cyanophenyl)-phenylthionophos-phonat 0-Ethyl-0- (2,5-dichloro-4-cyanophenyl) phenylthionophosphate
Die Titelverbindung wird analog Beispiel 1 oder 2 aus O-Äthyl-phenylthionophosphonsäurechlorid und 2,5-Dichlor-4-cyanophenol erhalten. The title compound is obtained analogously to Example 1 or 2 from O-ethyl-phenylthionophosphonic acid chloride and 2,5-dichloro-4-cyanophenol.
Brechungsindex: n2i> 1,5221; Ausbeute 87% d. Th. Refractive index: n2i> 1.5221; Yield 87% of theory Th.
Beispiel 8 Example 8
0-Äthyl-S-n-propyl-0-(2,5-dichlor-4-cyanophenyl)-thionothiol-phosphat 0-ethyl-S-n-propyl-0- (2,5-dichloro-4-cyanophenyl) thionothiol phosphate
Beispiel 2 Example 2
0,0-Diäthyl-0-(2,5-dichlor-4-cyanophenyl)-thionophosphat 132 g (0,7 Mol) 2,5-Dichlor-4-cyanophenol werden in 200 m 0.0-Diethyl-0- (2,5-dichloro-4-cyanophenyl) thionophosphate 132 g (0.7 mol) of 2,5-dichloro-4-cyanophenol are in 200 m
65 Die Titelverbindung wird entsprechend Beispiel 1 durch Umsetzung von O-Äthyl-S-n-propyl-thionothiolphosphorsäu-rechlorid mit 2,5-dichlor-4-cyanophenol erhalten. Brechungsindex: n2!) 1,5703; Ausbeute 78% d. Th. 65 The title compound is obtained according to Example 1 by reacting O-ethyl-S-n-propyl-thionothiolphosphoric acid chloride with 2,5-dichloro-4-cyanophenol. Refractive index: n2!) 1.5703; Yield 78% of theory Th.
627 476 627 476
Entsprechend den obigen Beispielen können ferner erhalten werden: According to the above examples, the following can also be obtained:
0,S-Dimethyl-0-(2,5-dichlor-4-cyanophenyl)-thionothiol-phosphat; 0, S-dimethyl-0- (2,5-dichloro-4-cyanophenyl) thionothiol phosphate;
0,S-Diäthyl-0-(2,5-dichlor-4-cyanophenyl)-thionothiolpho-sphat; 0, S-diethyl-0- (2,5-dichloro-4-cyanophenyl) thionothiolphosphate;
0,S-DiisopropyI-0-(2,5-dichlor-4-cyanophenyl)-thiono-thiolphosphat; 0, S-diisopropyl-0- (2,5-dichloro-4-cyanophenyl) thionothiol phosphate;
0-Äthyl-S-n-isopropyl-0-(2,5-dichlor-4-cyanophenyl)-thio-nothiolphosphat; 0-ethyl-S-n-isopropyl-0- (2,5-dichloro-4-cyanophenyl) thio-nothiol phosphate;
0-Äthyl-S-n-butyl-0-(2,5-dichlor-4-cyanophenyl)-thiono-thiolphosphat; 0-ethyl-S-n-butyl-0- (2,5-dichloro-4-cyanophenyl) thionothiol phosphate;
0-Äthyl-S-tert.-butyl-0-(2,5-dichlor-4-cyanophenyl)-thio-nothiolphosphat. 0-ethyl-S-tert-butyl-0- (2,5-dichloro-4-cyanophenyl) thio-nothiol phosphate.
M M
Claims (4)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762607176 DE2607176A1 (en) | 1976-02-21 | 1976-02-21 | THIONO or THIONOTHIOL PHOSPHORUS AND THIONOPHOSPHONIC ACID ESTER |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH627476A5 true CH627476A5 (en) | 1982-01-15 |
Family
ID=5970586
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH198477A CH627476A5 (en) | 1976-02-21 | 1977-02-17 | Pesticide |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS52102257A (en) |
| BE (1) | BE851629A (en) |
| CH (1) | CH627476A5 (en) |
| DE (1) | DE2607176A1 (en) |
| DK (1) | DK141937C (en) |
| ES (1) | ES456104A1 (en) |
| FR (1) | FR2341588A1 (en) |
| GB (1) | GB1530112A (en) |
| IL (1) | IL51491A (en) |
| IT (1) | IT1083471B (en) |
| NL (1) | NL7701731A (en) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1281570A (en) * | 1960-03-07 | 1962-01-12 | Yashima Kagaku Kogyo Kabushiki | New phosphoric and thio-phosphoric esters, their preparation process and insecticides containing them |
| NL7310390A (en) * | 1972-02-07 | 1975-01-28 | Celamerck Gmbh & Co Kg | Thiophosphoric - and thiophosphonic esters - by transesterification using a weak base as catalyst |
| FR2239475A2 (en) * | 1972-02-07 | 1975-02-28 | Celamerck Gmbh & Co Kg | Thiophosphoric - and thiophosphonic esters - by transesterification using a weak base as catalyst |
| AT321943B (en) * | 1972-02-07 | 1975-04-25 | Oicelamerck Gmbh & Co Kg | Process for the preparation of thionophosphorus or thionophosphonic acid esters |
-
1976
- 1976-02-21 DE DE19762607176 patent/DE2607176A1/en not_active Withdrawn
-
1977
- 1977-02-17 CH CH198477A patent/CH627476A5/en not_active IP Right Cessation
- 1977-02-18 IL IL51491A patent/IL51491A/en unknown
- 1977-02-18 DK DK70577A patent/DK141937C/en active
- 1977-02-18 JP JP1701377A patent/JPS52102257A/en active Pending
- 1977-02-18 BE BE175103A patent/BE851629A/en unknown
- 1977-02-18 GB GB6983/77A patent/GB1530112A/en not_active Expired
- 1977-02-18 NL NL7701731A patent/NL7701731A/en not_active Application Discontinuation
- 1977-02-18 IT IT48124/77A patent/IT1083471B/en active
- 1977-02-19 ES ES456104A patent/ES456104A1/en not_active Expired
- 1977-02-21 FR FR7704959A patent/FR2341588A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL7701731A (en) | 1977-08-23 |
| GB1530112A (en) | 1978-10-25 |
| DK70577A (en) | 1977-08-22 |
| ES456104A1 (en) | 1978-02-01 |
| IL51491A (en) | 1980-12-31 |
| BE851629A (en) | 1977-08-18 |
| DK141937B (en) | 1980-07-21 |
| FR2341588A1 (en) | 1977-09-16 |
| DK141937C (en) | 1980-12-01 |
| DE2607176A1 (en) | 1977-09-01 |
| IL51491A0 (en) | 1977-04-29 |
| IT1083471B (en) | 1985-05-21 |
| JPS52102257A (en) | 1977-08-27 |
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| Date | Code | Title | Description |
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| PL | Patent ceased |