CH303952A - Process for the manufacture of a pesticide. - Google Patents
Process for the manufacture of a pesticide.Info
- Publication number
- CH303952A CH303952A CH303952DA CH303952A CH 303952 A CH303952 A CH 303952A CH 303952D A CH303952D A CH 303952DA CH 303952 A CH303952 A CH 303952A
- Authority
- CH
- Switzerland
- Prior art keywords
- condensation product
- compound
- phosphorus
- moles
- phosphite
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000000575 pesticide Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 17
- 241000607479 Yersinia pestis Species 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000007859 condensation product Substances 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 claims 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 claims 1
- -1 carboxylic acid halide Chemical class 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 150000003254 radicals Chemical group 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000007921 spray 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
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 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
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 239000002253 acid Substances 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
- 239000000443 aerosol Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 238000009835 boiling Methods 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
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- BJQNLIAFYAFGLD-UHFFFAOYSA-N dodecyl diethyl phosphite Chemical compound CCCCCCCCCCCCOP(OCC)OCC BJQNLIAFYAFGLD-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 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
- 210000003746 feather Anatomy 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000013305 food Nutrition 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
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002917 insecticide Substances 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
- 239000007788 liquid Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 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
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- SJHCUXCOGGKFAI-UHFFFAOYSA-N tripropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC(C)C SJHCUXCOGGKFAI-UHFFFAOYSA-N 0.000 description 1
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent 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
-
- 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
-
- 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)]
- C07F9/42—Halides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
Description
Verfahren zur Herstellung eines Schädlingsbekämpfungsmittels: Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung eines Schädlings- bekä.mpfimgsmittels, das dadurch gekennzeich net ist,
dass man als aktive Verbindung eine Halogen und Phosphor enthaltende Verbin dung mit der Atomgruppierung
EMI0001.0008
worin A1 und A" über ein Heteroatoni an (las Phosphoratom gebundene organische Reste und Hal ein Halogenatom bedeuten, mit. min destens einem inerten Trägerstoff mischt.
Die Verbindungen der genannten Formel stellen im allgemeinen hervorragend geeignete 1Iittel zur Bekämpfung tierischer Schädlinge dar; sie wirken auf deren verschiedene Ent wicklungsstufen, wie Eier, Larven, Imagines, wobei eine Wirkung als Kontakt-, Frass- oder Atmungsgift. in Betracht kommt.
Es können die verschiedensten Körper ge genüber Schädlingen geschützt werden. Als derartige zii schützende Körper kommen in Frage z. B. Luft, insbesondere in Räumüich- keiten, dann Flüssigkeiten, wie z. B. Wasser in Teichen, und schliesslich jegliche tote und lebende feste Unterlage, wie z.
B. beliebige Gegenstände in bewohnten Zimmern, in Kel lern, in Estrichen, in Stallungen, ferner Pelze, Federn, MTolle und dergleichen, sowie Lebe wesen des Pflanzen- und Tierreiches in ihren verschiedensten Entwicklungszuständen, so fern sie gegenüber den Schädlingsbekämp fungsmitteln unempfindlich sind.
Die Bekämpfung der Schädlinge mit den nach vorliegendem Verfahren hergestellten Mitteln kann nach üblichen Verfahren vorge nommen werden. Die neuen Mittel können in Form von Räucher-, Stäube- oder Spritzmit- teln verwendet werden, z. B. als Lösungen bzw. Suspensionen, die mit Wasser oder ge eigneten organischen Lösungsmitteln, wie z. B.
Alkohol, Petroleum, Teerdestillaten u. a., zu bereitet worden sind; auch können wässerige Lösungen bzw. wässerige Emulsionen von or ganischen Lösungsmitteln, die die wirksamen Stoffe enthalten, zum Bestreichen, Bespritzen oder Tauehen der zu schützenden Gegenstände dienen. Zur Herstellung von als Ärosole zu verwendenden Präparaten können als Lö- sungs- und Treibmittel z. B. Fluortrichlor- methan und Difluor-dichlormethan herange zogen werden.
Die Spritz- und Stäubmittel können die üblichen inerten Füllstoffe oder Zeichnungs mittel, wie z. B. Kaolin, Gips oder Bentonit oder weitere Zusätze, wie Sulfitcelluloseab- lauge, Gellulosederivate und dergleichen, fer ner zur Verbesserung der Netz- und Haft festigkeit die üblichen Netz- -und Haftmittel beigemischt enthalten.
Die Schädlingsbekämp- funggspräparate können in Pulverform, in Form von wässerigen Dispersionen -resp. Pa- sten oder als selbstdispergierende Öle herge stellt werden.
Die Verbindungen der eingangs genannten Formel können als einzige Wirkstoffe in einem Schädlingsbekämpfungsmittel vorhanden sein oder auch in Kombination mit. andern Insek- ticiden und/oder Fungiciden.
Die für die erfindungsgemässen Schäd- lingsbekämpf ungsmittel her anzuziehenden Ver bindungen der eingangs erwähnten allgemei nen Formel können hergestellt werden, wenn man 2 Mol einer Verbindung der allgemeinen Formel
EMI0002.0011
worin R1, Rg und R3 organische Reste, und X und Y -0-, -S-, -NH- oder >NRl bedeuten, mit.
1 Mol eines Carbonsä.ureha- logenids der allgemeinen Formel
EMI0002.0020
worin R4 einen Rest wie R.1, Wasserstoff oder ein Halogenatom und Hal ein Halogenatom bedeuten, unter Abspaltung von 2 Mol einer Verbindung Hal-R3 umsetzt.
Die als Ausgangsmaterialien benützbaren Verbindungen der allgemeinen Formel
EMI0002.0027
leiten sich vom 3wertigen Phosphor ab, wäh rend die Kondensationsprodukte Derivate des 5wertigen Phosphors sind. Unter den Verbindungen der soeben an geführten Formel sind. diejenigen, in denen die Symbole N und Y für Sauerstoff stehen, am leichtesten zugä.nglieh. Sie entsprechen der allgemeinen Formel
EMI0002.0033
und können nach bekannten Methoden herge stellt werden.
Die aliphatisehen Reste, die durch die Symbole R1, R= und R3 dargestellt werden, können geradkettig, verzweigt, gesättigt, oder ungesättigt sein; ferner können sie substi tuiert oder nnsubstituiert sein. Genannt seien z.
B. folgende Gruppen: 3lethyl-, Äthyl-, Pro py1-, Isopropyl-, Butyl-, Hexyl-, 2--@thylbutyl-, Oetyl-, 2-Butyl-oetyl-, Lauryl-, Octadeeyl-, Allyl-, 2-Chloräthyl-., ferner Radikale mit.
Rhodan-, Cyan- oder Estergruppen. Die 3 Reste R1, R. und R; können gleich oder ver schieden sein. Beispielsweise \seien folgende Verbindungen genannt:
Trimethylphosphit, Triäthylphosphit, Tripropylphosphit, Diäthyl- laurylphosphit oder Tri-2-eliloräthy lphospliit. Die aromatischen Radikale. die dureli R1, R:., und R3 dargestellt werden. können ein- oder mehrkernig sein und können gegebenenfalls noch Kernsubstituenten tragen:
erwähnt seien Phenyl-, 2- oder 4-Chlorphenyl-, 2.4-Dielilor- phenyl-, -I-I\Titropheny 1-, -1-llethoxyplienyl-, Naphthyl- oder 1-Diplienyl-reste. Es können Verbindungen verwendet werden, in denen alle 3 Reste R1, R. und R.3 ein aromatisches Hadilzal darstellen.
Vorzugsweise werden sol- elie Verbindungen herangezogen, in denen das Sz-mbol R:, für einen niedrigmolekularen ali- phatisehen Rest stellt, wie 2,1-Diehlorphenyl- diäthylp'hosphit oder p-Clilorplienyl-dimetlivl- phosphit. Von den araliphatisehen Radikalen, die durch Ri., R" und R;
dargestellt werden, sei der Benzvl-, von den eveloalipliatisehen der Cyelohexyl- und von den heterocyclischen der Tetrahy drofurfiirylrest erwähnt.
Unter den für die Kondensation benütz baren Carbonsäurehalogeniden werden vor zugsweise die Carbonsäureehloride herange zogen. Geeignete Säurechloride sind beispiels weise diejenigen von mindestens zweifach ha- log, genierten Essigsäuren, insbesondere das Tri- eliloi@essi-säurechlorid.
Die Kondensation erfolgt durch Umset zung der Komponenten in dem oben erwähn ten Mengenverhältnis. Sie führt zu einheit lichen Produkten. Weil die Reaktion oft exotherin verläuft, ist es gegebenenfalls not- vendig, die Komponenten unter Kühlung zu vereiiii@gen und mit inerten Lösungsmitteln, wie Benzol, Toluol, Ätlier, Dioxan, Hexan oder tiefsiedendem Benzin zu verdünnen. Die Re aktion wird vorteilhaft durch Erwärmen auf etwa<B>50-1200</B> C beendet.
Bei geeigneter Wahl der Reaktionskomponenten lassen sich die Kondensationsprodukte unter vermindertem Druck destillieren.
Zu 3Jisehungen von Produkten gelangt man, wenn man an Stelle von 2 Mol einer Verbindung, der allgemeinen Formel
EMI0003.0030
Worin Ri, R2, R;,, K und Y die eingangs gegebene Bedeutung haben, je 1 Mol von zwei verschiedenen Verbindungen der soeben an geführten allgemeinen Formel verwendet.
Im folgenden sei die Herstellung von Ver bindungen beschrieben, die in den erfindungs gemässen Schädlingsbekämpfungsmitteln ver wendet werden können.
Zu einer Lösung von 9,0 Teilen Trichlor- aeetylehlorid in 30 Volumteilen trockenem Äther wird unter Rühren bei -5 eine Lösung von 1.7,6 Teilen Triäthylphosphit in 70 Volumteilen Äther langsam zugegeben.
.Jede Zugabe bewirkt eine heftige Reaktion und Temperatursteigerung. Nachdem alles eingetragen ist, wird die Reaktionsmisehung 30 Minuten bei Raumtemperatur stehenge lassen, während 30 Minuten unter Rückfluss zum Kochen erhitzt und hierauf der Äther abdestilliert. Der sich anfangs bildende kri stallinische Körper löst sich im Verlaufe der Reaktion wieder. Nachdem der Äther entfernt ist, wird bei 100-110 C im Vakuum zuerst alles Flüchtige entfernt und anschliessend der Rückstand fraktioniert. Bei 136-138 /0,1 mm destilliert unter teilweiser, geringer Zerset- 7ung das Kondensationsprodukt als ein farb loses Öl.
Verwendet man an Stelle des Triäthyl- phosphites eine äquivalente Menge Triisopro- pylphosphit oder Trimethylphosphit, so ge langt man zu Produkten mit ähnlichen Eigen schaften.
Method for the production of a pest control agent: The present invention relates to a method for the production of a pest control agent, which is characterized in that
that the active compound is a compound containing halogen and phosphorus with the atom group
EMI0001.0008
where A1 and A "are organic radicals bonded to the phosphorus atom via a heteroatom and Hal is a halogen atom, mixed with at least one inert carrier.
The compounds of the formula mentioned are generally eminently suitable agents for combating animal pests; they act on their various stages of development, such as eggs, larvae, and imagines, with an effect as a contact, food or respiratory poison. comes into consideration.
A wide variety of bodies can be protected against pests. As such zii protective bodies come into question z. B. air, especially in rooms, then liquids such. B. water in ponds, and finally any dead and living solid surface, such.
B. any objects in inhabited rooms, in cellars, in screeds, in stables, also furs, feathers, MTolls and the like, as well as creatures of the plant and animal kingdom in their various stages of development, as far as they are insensitive to pesticides.
The control of the pests with the agents prepared by the present process can be carried out by customary methods. The new agents can be used in the form of incense, dust or spray, z. B. as solutions or suspensions with water or ge suitable organic solvents such. B.
Alcohol, petroleum, tar distillates, etc. a., to have been prepared; Aqueous solutions or aqueous emulsions of organic solvents which contain the active substances can also be used to paint, spray or thaw the objects to be protected. For the production of preparations to be used as aerosols, solvents and propellants such as B. fluorotrichloromethane and difluorochloromethane are used.
The spray and dust can medium, the usual inert fillers or drawing, such as. B. kaolin, gypsum or bentonite or other additives such as sulphite cellulose liquor, cellulose derivatives and the like, also contain the usual wetting agents and adhesives mixed in to improve the wetting and adhesive strength.
The pest control preparations can be in powder form, in the form of aqueous dispersions - resp. Pastes or as self-dispersing oils.
The compounds of the formula mentioned at the outset can be present as the only active ingredients in a pesticide or else in combination with. other insecticides and / or fungicides.
The compounds of the general formula mentioned at the beginning to be used for the pesticides according to the invention can be prepared by adding 2 moles of a compound of the general formula
EMI0002.0011
wherein R1, Rg and R3 are organic radicals, and X and Y are -0-, -S-, -NH- or> NRl, with.
1 mol of a carboxylic acid halide of the general formula
EMI0002.0020
wherein R4 is a radical such as R.1, hydrogen or a halogen atom and Hal is a halogen atom, converts Hal — R3 with elimination of 2 mol of a compound.
The compounds of the general formula which can be used as starting materials
EMI0002.0027
derive from trivalent phosphorus, while the condensation products are derivatives of pentavalent phosphorus. Among the compounds of the formula just given are. those in which the symbols N and Y represent oxygen are most easily accessible. They correspond to the general formula
EMI0002.0033
and can be Herge using known methods.
The aliphatic radicals which are represented by the symbols R1, R R and R3 can be straight-chain, branched, saturated or unsaturated; they can also be substituted or unsubstituted. For example
B. the following groups: 3lethyl, ethyl, propy1, isopropyl, butyl, hexyl, 2 - @ thylbutyl, oetyl, 2-butyl-oetyl, lauryl, octadeeyl, allyl, 2-Chloräthyl-., Also radicals with.
Rhodane, cyano or ester groups. The 3 residues R1, R. and R; can be the same or different. For example \ the following connections are mentioned:
Trimethyl phosphite, triethyl phosphite, tripropyl phosphite, diethyl lauryl phosphite or tri-2-eliloräthy lphospliit. The aromatic radicals. the dureli R1, R:., and R3 are represented. can be mononuclear or polynuclear and can optionally also carry core substituents:
Phenyl, 2- or 4-chlorophenyl, 2,4-Dielilor- phenyl, -I-I \ Titropheny 1-, -1-llethoxyphenyl, naphthyl or 1-diplienyl radicals may be mentioned. It is possible to use compounds in which all 3 radicals R1, R. and R.3 represent an aromatic hadilzal.
It is preferred to use those compounds in which the Sz-mbol R: represents a low molecular weight aliphatic radical, such as 2,1-dichlorophenyl diethyl phosphite or p-chloroplienyl dimethyl phosphite. Of the Araliphatic radicals indicated by Ri., R "and R;
the Benzyl radical, the cyelohexyl radical from the eveloalipliatis and the tetrahydrofurfuryl radical from the heterocyclic ones.
Among the carboxylic acid halides usable for the condensation, the carboxylic acid chlorides are preferably used. Suitable acid chlorides are, for example, those of at least doubly halogenated acetic acids, in particular the trilillo @essi acid chloride.
The condensation takes place through the implementation of the components in the proportions mentioned above. It leads to uniform products. Because the reaction is often exothermic, it may be necessary to multiply the components with cooling and to dilute them with inert solvents such as benzene, toluene, etlier, dioxane, hexane or low-boiling gasoline. The reaction is advantageously terminated by heating to about 50-1200C.
With a suitable choice of the reaction components, the condensation products can be distilled under reduced pressure.
3Jisehungen of products are obtained if instead of 2 mol of a compound of the general formula
EMI0003.0030
Wherein Ri, R2, R; ,, K and Y have the meaning given at the beginning, each 1 mol of two different compounds of the general formula just given is used.
The following describes the production of compounds that can be used in the pesticides according to the invention.
To a solution of 9.0 parts of trichloroetyl chloride in 30 parts by volume of dry ether, a solution of 1.7.6 parts of triethyl phosphite in 70 parts by volume of ether is slowly added while stirring at -5.
Each addition causes a violent reaction and temperature increase. After everything has been entered, the reaction mixture is left to stand for 30 minutes at room temperature, refluxed for 30 minutes and the ether is then distilled off. The initially formed crystalline body dissolves again in the course of the reaction. After the ether has been removed, all volatiles are first removed at 100-110 C in vacuo and the residue is then fractionated. At 136-138 / 0.1 mm, the condensation product distills as a colorless oil with partial, slight decomposition.
If an equivalent amount of triisopropyl phosphite or trimethyl phosphite is used in place of the triethyl phosphite, products with similar properties are obtained.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH303952T | 1951-09-25 |
Publications (1)
Publication Number | Publication Date |
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CH303952A true CH303952A (en) | 1954-12-31 |
Family
ID=4491902
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CH303952D CH303952A (en) | 1951-09-25 | 1951-09-25 | Process for the manufacture of a pesticide. |
Country Status (1)
Country | Link |
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CH (1) | CH303952A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1034410B (en) * | 1955-05-20 | 1958-07-17 | California Spray Chemical Corp | Insecticidal agent |
US2934469A (en) * | 1956-01-30 | 1960-04-26 | Monsanto Chemicals | Phosphinylvinyl phosphates |
US2983645A (en) * | 1955-05-20 | 1961-05-09 | California Research Corp | Reaction product of triethyl phosphite and trichloroacetyl chloride as an insecticide |
-
1951
- 1951-09-25 CH CH303952D patent/CH303952A/en unknown
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1034410B (en) * | 1955-05-20 | 1958-07-17 | California Spray Chemical Corp | Insecticidal agent |
US2983645A (en) * | 1955-05-20 | 1961-05-09 | California Research Corp | Reaction product of triethyl phosphite and trichloroacetyl chloride as an insecticide |
US2934469A (en) * | 1956-01-30 | 1960-04-26 | Monsanto Chemicals | Phosphinylvinyl phosphates |
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