CH335067A - Process for the preparation of new halogen and phosphorus containing compounds - Google Patents
Process for the preparation of new halogen and phosphorus containing compoundsInfo
- Publication number
- CH335067A CH335067A CH335067DA CH335067A CH 335067 A CH335067 A CH 335067A CH 335067D A CH335067D A CH 335067DA CH 335067 A CH335067 A CH 335067A
- Authority
- CH
- Switzerland
- Prior art keywords
- 2pcc12c00
- preparation
- containing compounds
- phosphorus containing
- formula
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims description 4
- 229910052736 halogen Inorganic materials 0.000 title claims description 4
- 150000002367 halogens Chemical class 0.000 title claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 title claims description 4
- 239000011574 phosphorus Substances 0.000 title claims description 4
- -1 aryl trichloroacetate Chemical compound 0.000 claims description 5
- 229940066528 trichloroacetate Drugs 0.000 claims description 2
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 241000607479 Yersinia pestis Species 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UAMJIPWXLGMBPW-UHFFFAOYSA-N (4-chlorophenyl) 2,2,2-trichloroacetate Chemical compound ClC1=CC=C(OC(=O)C(Cl)(Cl)Cl)C=C1 UAMJIPWXLGMBPW-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000252254 Catostomidae Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 208000001034 Frostbite Diseases 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000034303 cell budding Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-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
- 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
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000009736 wetting Methods 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
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Herstellung von neuen Halogen und Phosphor enthaltenden Verbindungen Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung neuer Halogen und Phosphor enthaltenden Verbindungen, die als Sehädlingsbekämpfimgsmittel Verwendung finden können und der allgemeinen Formel
EMI1.6
entsprechen, worin R und R1 gleiche oder v er- schiedene, niedrigmolekulare, aliphatische Reste und R2 einen aromatischen Rest. bedeuten.
Die aliphatisehen Reste R und R1 können geradkettig, verzweigt, gesättigt oder ungesättigt sein; ferner können sie substituiert oder unsubstituiert sein. Genannt seien zum Beispiel folgende Gruppen: 1Iethyl-, Äthyl-, Propyl-, Isopropyl-, Bu- tyl-, Allyl-, 2-Chloräthyl-, ferner Radikale mit Rhodan-, Cyan- oder Estergruppen. Die Reste können gleich oder verschieden sein.
Der aromatische Rest R, kann ein- oder mehrkernig sein und kann gegebenenfalls noch Kernsub- stituenten tragen; erwähnt seien Pheny 1-, 2- oder 4-Chlorphenyl-, 2,4-Dimethylpheny 1-, 4- llethoxyphenyl-, 4-Nitrophenyl-, Naphthyl- oder 4-Diphenyl-reste.
Das erfindungsgemässe Verfahren ist dadurch gekennzeichnet, dass man eine Verbindung der allgemeinen Formel
EMI1.40
worin R und R1 die oben gegebene Bedeutung haben, mit einem Trichloressigsäiuearylester umsetzt.
Da bei der Umsetzung die Reaktion oft exotherm verläuft, ist es gegebenenfalls notwendig, die Komponenten unter Kühlung zu vereinigen und mit inerten Lösungsmitteln wie Benzol, Toluol, Äther, Dioxan, Hexan oder tiefsiedendem Benzin zu verdünnen. Die Reaktion wird vorteilhaft durch Erwärmen auf etwa 50 bis 120 beendet. Bei geeigneter Wahl der Reaktionskomponenten lassen sich die Kondensationsprodukte unter vermindertem Druck destillieren.
Die Bekämpfung der Schädlinge wird nach üblichen Verfahren vorgenommen, z. B. durch Behandlung der zu schützenden Körper mit den neuen Verbindungen in Form von Stäube- oder Spritzmitteln, z. B. als Lösungen bzw. Suspensionen, die mit Wasser oder geeigneten organischen Lösungsmitteln, nie z.
B. Alkohol, Petroleum, Teerdestillaten u. a., zubereitet worden sind; auch können wässrige Lösungen bzw. wässrige Emulsionen von organischen Lösungsmitteln, die die wirksamen Stoffe enthalten, zum Bestreichen, Bespritzen oder Tauchen der zu schützenden Gegenstände dienen.
<Desc/Clms Page number 2>
Die Spritz- und Stäubemittel können die üblichen inerten Füllstoffe oder Zeichnungsmittel, wie z. B.
Kaolin, Gips oder Bentonit oder weitere Zusätze, wie Sulfitcellulose- ablauge, Cellulosederivate und dergleichen, ferner zur Verbesserung der Netzfähigkeit und Haftfestigkeit die üblichen Netz- und Haftmittel beigemischt. enthalten. Die Schäd- lingsbekämpfimgspräparate können in Pulverform, in Form von wässrigen Dispersionen resp. Pasten oder als selbstdispergierende öle hergestellt werden.
Die neuen Verbindungen können als einzige Wirkstoffe in einem Schädlingsbekämpfungsmittel vorhanden sein oder auch in Kombination mit. andern Insekticiden und/oder Fungiciden. Die Verwendung solcher Präparate im Pflanzenschutz erfolgt nach den üblichen Spritz- und Stäubeverfahren.
Gegenüber bekannten Schädlingsbekämpfungsmitteln, bei welchen der Rest R:, der eingangs erwähnten Formel einen alipliatisehen Rest bedeutet, besitzen die Verbindungen der vorliegenden Erfindung im allgemeinen den Vorteil, dass sie bei guter Wirksamkeit gegen- über den Schädlingen eine geringere Toxieität für Warmblüter aufweisen.
In den folgenden Beispielen bedeuten Teile Gewichtsteile. Das Verhältnis von Gewichtsteil zu Volumteil ist das gleiche wie dasjenige zwischen dem Kilogramm und dem Liter. Die Temperaturen sind in Celsiusgraden angegeben.
Beispiel 1 Zu einer Lösung von 6,6 Teilen Trimethyl- phosphit in 10 Volumteilen Benzol werden 13,6 Teile Trichloressigsäure-p-chlorphenol- ester zugegeben. Hierauf wird auf etwa 60 aufgeheizt., worauf die Reaktion unter Gasentwicklung einsetzt. Wenn dieselbe nachlässt und die Temperatur zu fallen beginnt, wird während 20 Minuten auf dem Dampfbad unter Rückflusskühlung erwärmt, worauf die Reaktion beendet. ist. Das Benzol wird im Vakuum abdestilliert, worauf man 17,3 Teile des Reaktionsproduktes der Formel
EMI2.32
erhält. Das Produkt destilliert bei 130 bis 135 /0,05 mm. Es ist eine farblose Flüssigkeit, die in Wasser unlöslich, in organischen Lösungsmitteln löslich ist.
Beispiel 2 In gleicher Weise wie in Beispiel 1 beschrieben können auch die folgenden Verbindungen hergestellt werden.
EMI2.33
Nr. Formel Siedepunkt 1 (C2H50)2PCC12C00-@ 0,02 mm 1I @@ 127-128o 0 2 (CHsO)2PCC12C00- 0,04 mm 125-1270 Il 0 3 (C2IH50)2PCC12C00-@-C1 0,04 mm 1I 135-140 0 4 (C2H50)2PCC12C00 _ 1I 0 Cl
<Desc/Clms Page number 3>
EMI3.1
Nr.
Formel Siedepunkt 5 (CH30)2PCC12C00@ _ 1I O Cl mm 6 (C21:150)2PCC12C00 0,04 -## 138-142 f1 O Cl 7 (CH30)2PCC12C00-O 0,03 mm 1I 115-125 O Cl (C2H50 )2PCC12C0 0- < > 1I CH3 O 9 (CH30)2PCC12C00 0,05 mm 1I @- 127-1290 0 CH3 10 (C2H50)2PCCI2C00-/--\-Cl 140-1450 'II O CH3 11 (CH30)2PCC12C00-@-C1 0,1 mm 1I 155-156 \CH3 12 (C2H50)2PCC12C00- < --:#z-N02 - 1I O 13 (CH30)2PCC12C00-/---,\-N02 - 1I O 14 (C2H50)2PCC1zC00-@ C5H11 0,03 mm 1I 155-1600 O mm 15 (CH30)2PCC12C00 --/# C5H11 0,03 153-155 Il 0
<Desc/Clms Page number 4>
EMI4.1
Nr.
Formel Siedepunkt 16 (C21150)2PCC12C0 0 -@-0 CH3 0,04 mm 154--155 1I 0 17 (CH30)2PCC12C00- 7--\ -OCH3 - 0 1s (C2H50)2PCC12C00-@- _ 1I 0 19 (CH30)2PCC12C00- < :DII - 0 20 (C2H50)2PCC12C00 0,04 mm 1I < 163-168 0 21 (CH30)2PCC12C00-O 0,07 mm 11 150-165 O 22 (C2H50)2PCC12C00- 0,03 mm 1I 165-175 O 23 (CH30)2PCC12C00- ö "J - 24 (C2H50)2PCC12C00@-CH3 0,04 mm 1I 140-141 0 25 (CH30)2PCC12c00-# -C113 0,2 mm 11 120-130o O 26 (C2H50)2PCC12C00-//---\*#' 0,04 mm 11 \1--/ 140-142 0 C113 27 (CH30)2PCC12C00@@ 0,06 mm 1I 135-1370 0 \C113
<Desc/Clms Page number 5>
EMI5.1
Nr.
Formel Siedepunkt 28 (C21-150)2PCC12C00 0,04 mm 1I l27-133 CH3 29 (CH30)2PCC12C00 0,04 mm 125-l27 1I 0 Cl-13 30 (C2H50)2PCC12C00- /-CH3 3'66 1I 0 CH3 31 (CH30)2PCC12C00-/-CH3 3'p4 1I 0 0 CH3 Verwendungsbeispiel Man mischt 5 Teile der nach Beispiel 1 erhältlichen Verbindung, 10 Teile Octylphe- nolpolyglykoläther, 5 Teile Ölsäure und 80 Teile Mineralöl. Man erhält ein selbst- dispergierendes Öl, da.ss sich ausgezeichnet als Winterspritzmittel eignet.
Bei Anwendung als 1 0/aige Spritzbrühe bei Obstbäumen kurz vor dem Austrieb im Frühjahr werden die überwinternden Stadien der Obstbaumsehädlinge, wie Wintereier von Blattläusen, Eier von Frostspannern oder Blattsaugern, ferner die überwinternden Schildläuse ab-
<Desc / Clms Page number 1>
Process for the production of new halogen and phosphorus-containing compounds The present invention relates to a process for the production of new halogen and phosphorus-containing compounds which can be used as pest control agents and which have the general formula
EMI1.6
correspond, where R and R1 are identical or different, low molecular weight, aliphatic radicals and R2 is an aromatic radical.
The aliphatic radicals R and R1 can be straight-chain, branched, saturated or unsaturated; they can also be substituted or unsubstituted. The following groups may be mentioned, for example: 1-ethyl, ethyl, propyl, isopropyl, butyl, allyl, 2-chloroethyl, and also radicals with rhodium, cyano or ester groups. The radicals can be the same or different.
The aromatic radical R 1 can be mononuclear or polynuclear and can optionally also carry nuclear substituents; Pheny 1-, 2- or 4-chlorophenyl, 2,4-dimethylphenyl 1-, 4-methoxyphenyl, 4-nitrophenyl, naphthyl or 4-diphenyl radicals may be mentioned.
The inventive method is characterized in that one compound of the general formula
EMI1.40
wherein R and R1 have the meaning given above, is reacted with an aryl trichloroacetate.
Since the reaction is often exothermic during the reaction, it may be necessary to combine the components with cooling and to dilute them with inert solvents such as benzene, toluene, ether, dioxane, hexane or low-boiling gasoline. The reaction is advantageously terminated by heating to about 50-120. With a suitable choice of the reaction components, the condensation products can be distilled under reduced pressure.
The pests are controlled by conventional methods, e.g. B. by treating the body to be protected with the new compounds in the form of dusts or sprays, e.g. B. as solutions or suspensions with water or suitable organic solvents, never z.
B. alcohol, petroleum, tar distillates u. a., have been prepared; Aqueous solutions or aqueous emulsions of organic solvents which contain the active substances can also be used for painting, spraying or dipping the objects to be protected.
<Desc / Clms Page number 2>
The spraying and dusting agents can be the usual inert fillers or drawing agents, such as. B.
Kaolin, gypsum or bentonite or other additives, such as sulphite cellulose waste liquor, cellulose derivatives and the like, and the usual wetting agents and adhesives are also added to improve the wetting ability and adhesive strength. contain. The pest control preparations can be in powder form, in the form of aqueous dispersions, respectively. Pastes or as self-dispersing oils.
The new compounds can be present as the only active ingredients in a pesticide or in combination with. other insecticides and / or fungicides. The use of such preparations in crop protection takes place according to the usual spray and dusting methods.
Compared with known pesticides in which the radical R :, of the formula mentioned at the outset denotes an aliphatic radical, the compounds of the present invention generally have the advantage that they are more effective than pests and are less toxic to warm-blooded animals.
In the following examples, parts mean parts by weight. The ratio of part by weight to part by volume is the same as that between the kilogram and the liter. The temperatures are given in degrees Celsius.
EXAMPLE 1 13.6 parts of p-chlorophenol trichloroacetate are added to a solution of 6.6 parts of trimethyl phosphite in 10 parts by volume of benzene. This is followed by heating to about 60, whereupon the reaction begins with evolution of gas. When this subsides and the temperature begins to drop, reflux is carried out on the steam bath for 20 minutes, after which the reaction is terminated. is. The benzene is distilled off in vacuo, whereupon 17.3 parts of the reaction product of the formula
EMI2.32
receives. The product distills at 130 to 135 / 0.05 mm. It is a colorless liquid that is insoluble in water, soluble in organic solvents.
Example 2 In the same manner as described in Example 1, the following compounds can also be prepared.
EMI2.33
Formula Boiling point 1 (C2H50) 2PCC12C00- @ 0.02 mm 1I @@ 127-128o 0 2 (CHsO) 2PCC12C00- 0.04 mm 125-1270 Il 0 3 (C2IH50) 2PCC12C00 - @ - C1 0.04 mm 1I 135-140 0 4 (C2H50) 2PCC12C00 _ 1I 0 Cl
<Desc / Clms Page number 3>
EMI3.1
No.
Formula Boiling point 5 (CH30) 2PCC12C00 @ _ 1I O Cl mm 6 (C21: 150) 2PCC12C00 0.04 - ## 138-142 f1 O Cl 7 (CH30) 2PCC12C00-O 0.03 mm 1I 115-125 O Cl ( C2H50) 2PCC12C0 0- <> 1I CH3 O 9 (CH30) 2PCC12C00 0.05 mm 1I @ - 127-1290 0 CH3 10 (C2H50) 2PCCI2C00 - / - \ - Cl 140-1450 'II O CH3 11 (CH30) 2PCC12C00 - @ - C1 0.1 mm 1I 155-156 \ CH3 12 (C2H50) 2PCC12C00- <-: # z-N02 - 1I O 13 (CH30) 2PCC12C00 - / ---, \ - N02 - 1I O 14 (C2H50) 2PCC1zC00- @ C5H11 0.03 mm 1I 155-1600 O mm 15 (CH30) 2PCC12C00 - / # C5H11 0.03 153-155 Il 0
<Desc / Clms Page number 4>
EMI4.1
No.
Formula boiling point 16 (C21150) 2PCC12C0 0 - @ - 0 CH3 0.04 mm 154--155 1I 0 17 (CH30) 2PCC12C00- 7 - \ -OCH3 - 0 1s (C2H50) 2PCC12C00 - @ - _ 1I 0 19 ( CH30) 2PCC12C00- <: DII - 0 20 (C2H50) 2PCC12C00 0.04 mm 1I <163-168 0 21 (CH30) 2PCC12C00-O 0.07 mm 11 150-165 O 22 (C2H50) 2PCC12C00- 0.03 mm 1I 165-175 O 23 (CH30) 2PCC12C00- ö "J - 24 (C2H50) 2PCC12C00 @ -CH3 0.04 mm 1I 140-141 0 25 (CH30) 2PCC12c00- # -C113 0.2 mm 11 120-130o O 26 (C2H50) 2PCC12C00 - // --- \ * # '0.04 mm 11 \ 1 - / 140-142 0 C113 27 (CH30) 2PCC12C00 @@ 0.06 mm 1I 135-1370 0 \ C113
<Desc / Clms Page number 5>
EMI5.1
No.
Formula boiling point 28 (C21-150) 2PCC12C00 0.04 mm 1I l27-133 CH3 29 (CH30) 2PCC12C00 0.04 mm 125-l27 1I 0 Cl-13 30 (C2H50) 2PCC12C00- / -CH3 3'66 1I 0 CH3 31 (CH30) 2PCC12C00 - / - CH3 3'p4 1I 0 0 CH3 Example of use 5 parts of the compound obtainable according to Example 1, 10 parts of octylphenol polyglycol ether, 5 parts of oleic acid and 80 parts of mineral oil are mixed. The result is a self-dispersing oil that is ideally suited as a winter spray.
When used as a 1 0 / aige spray mixture on fruit trees shortly before budding in spring, the wintering stages of the fruit tree pests, such as winter eggs from aphids, eggs from frostbite or leaf suckers, and also the wintering scale insects.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH335067T | 1955-09-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH335067A true CH335067A (en) | 1958-12-31 |
Family
ID=4503425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH335067D CH335067A (en) | 1955-09-12 | 1955-09-12 | Process for the preparation of new halogen and phosphorus containing compounds |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH335067A (en) |
-
1955
- 1955-09-12 CH CH335067D patent/CH335067A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1445949A1 (en) | Process for the preparation of pyrimidine derivatives | |
| DE1068699B (en) | Process for the preparation of thiol or thionothiol phosphoric acid esters | |
| DE1062237B (en) | Process for the preparation of O, O-dialkylthiolphosphoric acid and -thiolthionophosphoric acid-S-gamma-cyanallyl esters | |
| CH335067A (en) | Process for the preparation of new halogen and phosphorus containing compounds | |
| DE1518692C3 (en) | Pesticides containing N- <2-ethyl-4-bromophenyl) -N ', N'-dimethylformamidine | |
| DE1139492B (en) | Process for the production of dithiolphosphonic acid esters | |
| CH468153A (en) | Insecticides | |
| DE974569C (en) | Pest repellants | |
| DE2221500A1 (en) | ISOTHIOURA COMPOUNDS, PROCESS FOR THEIR PRODUCTION AND THEIR USE AS MICROBICIDES | |
| CH331847A (en) | Process for the preparation of new compounds containing halogen and phosphorus | |
| DE1140776B (en) | Pest repellants | |
| DE2232076A1 (en) | ORGANIC PHOSPHORIC ACID ESTERS, PROCESS FOR THEIR PRODUCTION AND THEIR USE AS INSECTICIDES, ACARICIDES AND NEMATOCIDES | |
| DE1300113B (en) | Phosphoric dithiophosphate and process for their preparation | |
| DE1074034B (en) | Process for the preparation of thiophosphoric acid esters | |
| CH303952A (en) | Process for the manufacture of a pesticide. | |
| DE2321522C2 (en) | Insecticidal agent for combating caterpillar feeding on leaves | |
| AT229632B (en) | Pesticides containing organic phosphorus compounds | |
| DE1136328B (en) | Process for the production of dithiolphosphoric acid esters | |
| DE975092C (en) | Pest repellants | |
| DE2608506A1 (en) | NEW PHOSPHORUS COMPOUNDS, THEIR PRODUCTION AND COMPOSITIONS WITH THESE COMPOUNDS | |
| CH307235A (en) | Process for the manufacture of a pesticide. | |
| CH343177A (en) | Use of organic phosphorus compounds as pesticides | |
| DE2111672A1 (en) | Phosphonoglyoxylic acid esters - with insecticidal activity | |
| DE2150098B2 (en) | 1 ^ -triazolyl-S-phosphoric acid esters, their preparation and pesticides containing them | |
| CH392980A (en) | Pesticides containing organic phosphorus compounds |