DE1670983C3 - Pyridazinyl phosphorus (phosphonic) or thionophosphorus (phosphonic) acid esters, process for their preparation and their use - Google Patents
Pyridazinyl phosphorus (phosphonic) or thionophosphorus (phosphonic) acid esters, process for their preparation and their useInfo
- Publication number
- DE1670983C3 DE1670983C3 DE19681670983 DE1670983A DE1670983C3 DE 1670983 C3 DE1670983 C3 DE 1670983C3 DE 19681670983 DE19681670983 DE 19681670983 DE 1670983 A DE1670983 A DE 1670983A DE 1670983 C3 DE1670983 C3 DE 1670983C3
- Authority
- DE
- Germany
- Prior art keywords
- phosphonic
- phosphorus
- och
- thionophosphorus
- pyridazinyl
- 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.)
- Expired
Links
- -1 Pyridazinyl phosphorus Chemical compound 0.000 title claims description 9
- 239000002253 acid Substances 0.000 title claims description 8
- 150000002148 esters Chemical class 0.000 title claims description 3
- ZVAYUUUQOCPZCZ-UHFFFAOYSA-N 4-(diethoxyphosphorylmethyl)aniline Chemical compound CCOP(=O)(OCC)CC1=CC=C(N)C=C1 ZVAYUUUQOCPZCZ-UHFFFAOYSA-N 0.000 title description 5
- 238000000034 method Methods 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 6
- 241000238876 Acari Species 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000004458 analytical method Methods 0.000 description 15
- BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 description 5
- 239000005983 Maleic hydrazide Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 241000255925 Diptera Species 0.000 description 3
- 230000000895 acaricidal Effects 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000000749 insecticidal Effects 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- 241000276498 Pollachius virens Species 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002035 prolonged Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Description
OC2H5 OC 2 H 5
in der R1 -OCH5. -CH3. -C1H,. Phenyl; R, — OCH,. — OCH3; R3 — OC1H5. — OCH3. -CH3. — C H5, Phenyl und X Sauerstoff oder Schwefel darstellt.in the R 1 -OCH 5 . -CH 3 . -C 1 H ,. Phenyl; R, - OCH ,. - OCH 3 ; R 3 - OC 1 H 5 . - OCH 3 . -CH 3 . - CH 5 , phenyl and X represents oxygen or sulfur.
2. Verfahren zur Herstellung der Verbindungen gemäß Anspruch 1, dadurch gekennzeichnet, daß man in an sich bekannter Weise Phosphor-. Phosphon- bzw. Thionophosphor-(-phosphon-)-säureesterhalotienide der Formel2. Process for the preparation of the compounds according to claim 1, characterized in that one in a known manner phosphorus. Phosphonic or thionophosphorus (- phosphonic) - acid ester halides the formula
R1(R3) XR 1 (R 3 ) X
\il\ il
P-HaIP-HaI
C2H5O(R2)C 2 H 5 O (R 2 )
3535
mit Maleinsäurehydrazid in Gegenwart von Säurebindemitteln umsetzt, wobei R1, R2. Rj und X die im Anspruch 1 angegebene Bedeutung besitzen. Hai ein Halogenatom ist.with maleic hydrazide in the presence of acid binders, where R 1 , R 2 . Rj and X have the meaning given in claim 1. Hai is a halogen atom.
3. Insektizide und akarizide Mittel, gekennzeichnet durch einen Gehalt an Verbindungen gemäß Anspruch 1.3. Insecticidal and acaricidal agents, labeled by a content of compounds according to claim 1.
4545
In den deutschen Ausletieschriften 10 18 870 und 18 871 sowie der US-PS~ 27 59 938 werden bereits O,O-Dialkyi-O-[pyridazinyl-(3)]- bzw. -O-[pyrid- »zinon-(6)-yl-(3)j-phosphor- bzw. -thiono-phosphorsäureester beschrieben, welche insektizide und akarizidc Eigenschaften besitzen. Man kann diese Verbindungen unter anderem durch Umsetzung äquimolarer Mengen der entsprechenden Ο,Ο-Dialkyl-(thiono)phosphorsäurcesterchloride und Maleinsäurehydrazid herstellen.In the German Ausletie writings 10 18 870 and 18 871 and US-PS ~ 27 59 938 are already O, O-Dialkyi-O- [pyridazinyl- (3)] - or -O- [pyrid- »Zinon- (6) -yl- (3) j-phosphorus or -thiono-phosphoric acid ester described which insecticidal and acaricidal properties have. You can do this Compounds, inter alia, by reacting equimolar amounts of the corresponding Ο, Ο-dialkyl (thiono) phosphoric acid ester chlorides and produce maleic hydrazide.
Die Erfindung betrifft die in den Ansprüchen gekennzeichneten Pyridazinyl - phosphor - (phosphonl- bzw. - thionophosphor - (phosphonl - säureester, das Verfahren zu ihrer Herstellung und ihre Verwendung.The invention relates to the pyridazinyl phosphorus (phosphonl- or - thionophosphorus (phosphonic acid esters, the process for their preparation and their use.
Die neuen Produkte zeichnen sich durch hervorragende insektizide und akarizidc Eigenschaften aus. Sie besitzen ausgezeichnete Wirkung sowohl gegen fressende als auch saugende Insekten sowie gegenüberThe new products are characterized by excellent insecticidal and acaricidal properties. They have an excellent effect against both eating and sucking insects as well as against
M
!ί
CHCH
M.
! ί
CH
NHNH
NH
P-HaI + CH
ί Il
P-HaI + CH
ί
P—Hal-t
CH5O\ H
P — Hold
CH 5 O
ii X
ii
PI! ■
P.
t πCH
t π
i C.
i
H ■' X
H ■ '
C ί
C.
il -'X
il - '
[Hl![Hl!
C X R,C X R,
O -- PO - P
OCH,OCH,
In vorgenannten Gleichungen haben die Symbol R1. R2. R3. X und Hai die in dop. Ansprüchen auge gebene Bedeutung.In the above equations, the symbols have R 1 . R 2 . R 3 . X and Hai in dop. Claims given importance.
Bei Durchführung der Umsetzung verwendet mai das freie Maleinsäurehydrazid und läßt die Reaktio in Gegenwart von Säurebindernitteln ablaufen. Al besonders geeignet erwiesen sich Alkalialkoholat und -carbonate, ferner tertiäre aliphatische. arom;: tische oder heterocyclische Amine.When carrying out the implementation used mai the free maleic hydrazide and allows the reaction to proceed in the presence of acid-binding agents. Al Alkali alcoholates and carbonates, as well as tertiary aliphatic ones, have proven particularly suitable. arom ;: table or heterocyclic amines.
Das Verfahren wird bevorzugt unter Mitverwendun geeigneter Lösungs- und Verdünnungsmittel durcl geführt. Als solche kommen praktisch alle inerte organischen Solventicn oder Gemische derselben i Betracht, wie Kohler Wasserstoffe. Äther, ferner KiThe process is preferably carried out using suitable solvents and diluents guided. Practically all inert organic solvents or mixtures thereof come as such Consider how Kohler's hydrogens. Ether, furthermore Ki
tone; besonders, bewährt haben sich für den genannten Zweck jedoch niedrigsiedende aliphatische Alkohole, beispielsweise Methanol, Äthanol sowie vor allem Nitrile, z. B. Accio- und Propionilrü, ferner Dimethylformamid. tone; especially, have proven themselves for the said Purpose, however, low-boiling aliphatic alcohols, such as methanol, ethanol and above all Nitriles, e.g. B. Accio- and Propionilrü, also dimethylformamide.
Bei Durchführung der Umsetzung kann die Reaktionstemperatur innerhalb eines größeren Intervalls variiert werden, lin allgemeinen arbeitet man zwischen 30 und 70 C. Die umzusetzenden Ausgangsmalerialien sowie die Säurebindemittel werden im allgemeinen in äquimolaren Mengen eingesetzt.When carrying out the reaction, the reaction temperature can be within a relatively wide range can be varied, lin in general one works between 30 and 70 C. The starting materials to be converted as well as the acid binding agents are in general used in equimolar amounts.
Für den Fall, daß in den eingesetzten (Thiono)-Phosphor-(phosphon)-säureestcrhaiogeniden die Reste gleich sind, verwendet man 2 Mol Eslcrhalogenid pro Mol Maleinsäurehydrazid. Ai.dcrnfaHs wi.d zunächst 1 Mol Esterhaiogenid der FormelIn the event that the (Thiono) -Phosphor- (phosphonic) -äurestcrhaiogeniden used the radicals are the same, 2 moles of Eslcrhalogenid per mole of maleic hydrazide are used. Ai.dcrnfaHs wi.d first 1 mole of ester halide of the formula
R, XR, X
P-HaIP-HaI
C2H5OC 2 H 5 O
inner Rühren zu dem vorgelegten Male-nsäurchy- «lrazid getropft und nach einigen Stunden das Reaktionsgemisch mit einem Mol Esterhaiogenid der Formelinternal stirring to the submitted Male-nsäurchy- «Lazide was added dropwise and after a few hours the reaction mixture with one mole of ester halide of the formula
R, XR, X
\ I!\ I!
P-HaIP-HaI
versetzt.offset.
Nach Vereinigung der Ausgangskomponenten ist es vorteilhaft, die Mischung zwecks Vervollständigung der Umsetzung noch längere Zeit (3 bis 7 Stunden) zu rühren. Man erhält dann Verfahrensprodukte in guten Ausbeuten und großer Reinheit.After combining the starting components, it is advantageous to mix the mixture for the purpose of completion the reaction to stir for a longer time (3 to 7 hours). Process products are then obtained in good yields and great purity.
Die Phosphor- und Phosphon- bzw. Thionophosphor-(-phosphon-)-säurecster gemäß vorliegender Erfindung fallen teilweise in Form farbloser bis gelbgefärbter viskoser, wasserunlöslicher öle an, die durch sogenanntes »Andestilliercn«, d. h. längeres Erhitzen unter vermindertem Druck auf mäßig erhöhte Temperaturen von den letzten flüchtigen Anteilen befreit und auf diese Weise gereinigt werden können. Einige stellen kristallisierte Verbindungen dar, die sich durch Umkristallisieren aus den gebräuchlichen Lösungsmitteln gut reinigen lassen. Ihre Struktur ergibt sich aus den IR- und NMR-Spcktren.The phosphorus and phosphonic or thionophosphorus - (- phosphonic -) - acid esters according to the present invention fall partly in the form of colorless to yellow-colored viscous, water-insoluble oils, which are produced by so-called "distillation", d. H. prolonged heating freed from the last volatile constituents under reduced pressure to moderately elevated temperatures and can be cleaned in this way. Some represent crystallized compounds that stand out through Recrystallize well from the common solvents. Your structure arises from the IR and NMR spectra.
Die eriindungsgemäßen Verbindungen werden mit Erfolg im Pflanzenschulz zur Bekämpfung von schädlichen saugenden und fressenden Insekten und Dipteren sowie dort und auf dem vcterinär-mcdizinischen Sektor gegen Milben (Acarina) angewendet. Besonders hervorzuheben ist in diesem Zusammenhang die ausgezeichnete Wirksamkeit der Produkte gegen phosphorsäureestcr-resistcnte Stämme von Spinnmilben.The compounds according to the invention are successfully used in plant cultivation for combating harmful ones sucking and eating insects and dipteras as well as there and on the veterinary-medical Sector used against mites (acarina). Particularly noteworthy in this context is the excellent one Effectiveness of the products against phosphoric acid ester-resistant strains of spider mites.
Bei der Anwendung gegen Hygiene- und Vorratsschädlinge, besonders Fliegen und Mücken, zeichnen sich die neuen Produkte außerdem durch eine hervorragende Residualwirkung auf Holz und Ton sowie eine gute Alkalislabilität auf gekalkten Unterlagen aus.Draw when used against hygiene and storage pests, especially flies and mosquitoes The new products also have an excellent residual effect on wood and clay as well good alkali lability on limed substrates.
Je nach ihrem Anwendungszweck können die neuen Wirkstoffe in die üblichen Formulierungen übergeführt weiden, wie Lösungen, Emulsionen, Suspensionen, Pulver. Pasten und Granulate. Diese werden in bekannter Weise hergestellt.Depending on their intended use, the new active ingredients can be converted into the customary formulations graze, such as solutions, emulsions, suspensions, powders. Pastes and granules. These are in produced in a known manner.
Die Formulierungen enthalten im allgemeinen zwischen 0.1 bis 95 Gewichtsprozent Wirkstoff; vorzugsweise Bereiche liegen zwischen 0,5 und 90%.The formulations generally contain between 0.1 to 95 percent by weight of active ingredient; preferably Ranges are between 0.5 and 90%.
Die Vv'irkstoffköuzcnlranonen können, zwischen 0,(MXX)I und 20% und zwischen 0,01 und 5% variiert werden.The Vv'aktstoffköuzcnlranonen can, between 0, (MXX) I and 20% and between 0.01 and 5%.
Die folgenden Beispiele erläutern die Erfindung näher:The following examples explain the invention in more detail:
S OCH,S OCH,
I! / I! /
O —PO -P
/•N/ • N
C) - PC) - P
OC2H5 OC 2 H 5
OC1H5 OC 1 H 5
S OC2H5 S OC 2 H 5
Man löst 33 g (0.3 Mol) Maleinsäurehydrazid in 150ml Acetonitril. Diese lösung wird mit 60g (0.6 Mol) Triäthylamin versetzt. Anschließend tropfi man bei 40 C 116 g (0.6 Mol) O.O-Diäth\l-thionophosphorsäureesterchlorid zum Reaktionsgemisch und hält letzteres 3 Stunden bei dieser Temperatur. Danach wird die Mischung noch mehreie Stunden bei Zimmertemperatur gerührt, dann das ausgefallene Triälhylammoniumhydrochlorid abgesaugt, das FiI-iral mit etwas Wasser versetzt und in Chloroform aufgenommen. Die Chloroformschicht trocknet man. zieht d-is Lösungsmittel unter stark vermindertem Druck ab und destilliert das Reaktionsprodukt. Es schmilzt bei 78 C.33 g (0.3 mol) of maleic hydrazide are dissolved in 150 ml of acetonitrile. This solution comes with 60g (0.6 mol) of triethylamine added. Then drip one at 40 C 116 g (0.6 mol) O.O-dieth \ l-thionophosphoric acid ester chloride to the reaction mixture and keeps the latter for 3 hours at this temperature. The mixture is then kept at for several hours Stirred at room temperature, then the precipitated Triälhylammoniumhydrochlorid sucked off, the FiI-iral mixed with a little water and taken up in chloroform. The chloroform layer is dried. d-is solvent is drawn off under greatly reduced pressure and the reaction product is distilled. It melts at 78 C.
Die Aasbeute beträgt 105 g (84% der Theorie).The yield is 105 g (84% of theory).
Analyse für C12H22N2O6P2S2 (Molgewicht 416):
Berechnet ... N 6.74. P 14.92. S 15.40°,,:
gefunden .... N 7.21. P 14,82. S 14.76%.Analysis for C 12 H 22 N 2 O 6 P 2 S 2 (molecular weight 416):
Calculated ... N 6.74. P 14.92. S 15.40 ° ,,:
found .... N 7.21. P 14.82. S 14.76%.
Brechungsindex: n'i = 1,5159.Refractive index: n'i = 1.5159.
In analoger Weise können die folgenden Verbindungen hergestellt werden:The following connections can be established in an analogous manner:
4545 S CH,S CH,
O — PO - P
/; N N/ ; N N
VnVn
OCH5 OCH 5
OPOP
Il \Il \
S OC2H5 S OC 2 H 5
Jp.: 55 C.Jp .: 55 C.
Ausbeute: 26"ο der Theorie.Yield: 26 "ο the theory.
Analyse für C20H22N2O4P2S2 (Molgewicht 480):Analysis for C 20 H 22 N 2 O 4 P 2 S 2 (molecular weight 480):
Berechnet ... N 5.83. P 12,92. S 13.33%:
gefunden .... N 6.31. P 12.49. S 12,85%.Calculated ... N 5.83. P 12.92. S 13.33%:
found .... N 6.31. P 12.49. S 12.85%.
Fp.: 68 CM.p .: 68 C.
Ausbeute: 83.5% der Theorie.Yield: 83.5% of theory.
Analyse für C111H22N2O5P2S2 (Molgeurehf 4481: Berechnet ... N 6.24. P 11X3. S 14.29",,: uefunden .... N 6.21. P 13.93. S 13.94",,.Analysis for C 111 H 22 N 2 O 5 P 2 S 2 (Molgeurehf 4481: Calculated ... N 6.24. P 11X3. S 14.29 ",,: found .... N 6.21. P 13.93. S 13.94" ,, .
ii
S Il
S.
Fp.: 112 C.Fp .: 112 C.
Ausbeute: 49% der Theorie.Yield: 49% of theory.
Analyse Tür C10H1^N2O4P2S2 (Molgewicht 356|: Berechnet ... N 7.87. S 17.9S%: gefunden .... N 7.58. S 17.10",,.Analysis Door C 10 H 1 ^ N 2 O 4 P 2 S 2 (molecular weight 356 |: calculated ... N 7.87. S 17.9S%: found .... N 7.58. S 17.10 ",,.
S C2H5 SC 2 H 5
ο ρο ρ
OCH.,OCH.,
"N"N
!I ■-N ! I ■ -N
CH5 CH 5
C)C)
S OCMl5 S OCMl 5
Ip: 64 C.Ip: 64 C.
Ausbeute: 56",. der Theorie.Yield: 56 ",. Of theory.
Analyse für C12H22N2O4P2S, (Molgewicht 384): Berechne! ... N 7.29. P 16.15. SI6.6S",,: !•efunden .... N 7.45. P 16.18, S 16.62",,. O OC2H5 Analysis for C 12 H 22 N 2 O 4 P 2 S, (molecular weight 384): Calculate! ... N 7.29. P 16.15. SI6.6S ",,:! • found .... N 7.45. P 16.18, S 16.62" ,,. O OC 2 H 5
O-O-
J N Y N
C)C2H5 C) C 2 H 5
I ; 5 I ; 5
ο- ρο- ρ
O OC2H5 O OC 2 H 5
Ausbeute- 58",. der 1 heorie. Analyse für C12H22N2O..P2 !Molgewicht 384i:Yield 58 ",. Of the 1 theoretical analysis for C 12 H 22 N 2 O..P 2 ! Molecular weight 384i:
Berechnet . . . N 7.30. P) 6.) 5%: gefunden .... N 6.73. P 16.4S",,.Calculated . . . N 7.30. P) 6.) 5%: found .... N 6.73. P 16.4S ",,.
S OC2H, O PS OC 2 H, OP
; OC2H, ; OC 2 H,
N NN N
CH1 O- PCH 1 O-P
S OC2H,S OC 2 H,
Brechungsindex: /i. -- 1.5268. Ausbeute: 82",, der 1 heorie.Refractive index: / i. - 1.5268. Yield: 82 ", the 1 theory.
Analyse für C11H2nN2O5P2S2 (Mohewicht Berechnet ... N 7.26. P 16.07. S 16.59",,; gefunden .... N 7.37. P 16.26. S 15.95",,.Analysis for C 11 H 2n N 2 O 5 P 2 S 2 (Mohew weight Calculated ... N 7.26. P 16.07. S 16.59 ",,; found .... N 7.37. P 16.26. S 15.95" ,,.
S OC2Il, O P j OC2H*S OC 2 Il, OP j OC 2 H *
•••; N ' N••• ; N 'N
O P S OC2H,OPS OC 2 H,
Brechungsindex: n' - 1.5229. Ausbeute: Kl % der I heorie.Refractive index: n '- 1.5229. Yield: Kl% of I theory.
Analyse für C12H22N2O,P2S2 (Molgewicht 400):Analysis for C 12 H 22 N 2 O, P 2 S 2 (molecular weight 400):
Berechnet ... N 7.00. P 15.50. S 16.00",,: ücfunden .... N 7.32. P 15.44. S 15.50%.Calculated ... N 7.00. P 15.50. S 16.00 ",,: found .... N 7.32. P 15.44. S 15.50%.
S OCH5 S OCH 5
ο —ρο —ρ
I!I!
VnVn
OCM-UOCM-U
OC2IUOC 2 IU
ο—ρο — ρ
Il \ Il \Il \ Il \
O OC2H5 O OC 2 H 5
Brechungsindex: ιι'γ' = 1,4909. Ausbeute: 67.5% der Theorie.Refractive index: ιι'γ '= 1.4909. Yield: 67.5% of theory.
Analyse für C12H22O7N2P2S (Molgewicht 400):Analysis for C 12 H 22 O 7 N 2 P 2 S (molecular weight 400):
Berechnet ... N 7,00. P 15.50. S 8.00%; gefunden .... N 7.05. P 15.03. S 8.83%.Calculated ... N 7.00. P 15.50. S 8.00%; found .... N 7.05. P 15.03. S 8.83%.
S C0H,SC 0 H,
Il / ο—ρIl / ο-ρ
OC2H5 OC 2 H 5
VnVn
CH,CH,
ο—ρο — ρ
Il \Il \
S OC2H5 S OC 2 H 5
Ausbeute: 54% der Theorie. Analyse für C15H2nN2C)4P2S2 (Molgewicht 418):Yield: 54% of theory. Analysis for C 15 H 2n N 2 C) 4 P 2 S 2 (molecular weight 418):
Berechnet ... N 6.69. P 14.83. S 15,31%: gefunden .... N 7.35. P 15.24. S 15.47%.Calculated ... N 6.69. P 14.83. S 15.31%: found .... N 7.35. P 15.24. S 15.47%.
O — PO - P
OC2H5 OC 2 H 5
C2H5 O—PC 2 H 5 O-P
Il \Il \
S OC2H5 S OC 2 H 5
Ausbeute: 50% der Theorie. Analyse für C111H22N2O4P2S2 (Molgewicht 432):Yield: 50% of theory. Analysis for C 111 H 22 N 2 O 4 P 2 S 2 (molecular weight 432):
Berechnet ... N 6.50; ccfundcn .... N 6.34%.Calculated ... N 6.50; ccfundcn .... N 6.34%.
S C11H5 SC 11 H 5
I! /I! /
O—PO-P
OC2H5 OC 2 H 5
OC7H,OC 7 H,
O—PO-P
O OC2H5 O OC 2 H 5
Ausbeute: 77,5% der Theorie.Yield: 77.5% of theory.
S/C„HS O—PS / C "H S O-P
OC2H5 OC 2 H 5
;/N; / N
OCH, O —POCH, O -P
Il \ S OCH3 Il \ S OCH 3
Brechungsindex: Ut' = 1.5728. Ausbeute: 69% der Theorie.Refractive index: Ut '= 1.5728. Yield: 69% of theory.
* Analyse Tür C14H18N2O5P2S2 (Molgewicht* Analysis door C 14 H 18 N 2 O 5 P 2 S 2 (molecular weight
Berechnet ... N 6,67. P 14.78. S 15,25%: gefunden .... N 6.03. P 14.94. S 14.97%.Calculated ... N 6.67. P 14.78. S 15.25%: found .... N 6.03. P 14.94. S 14.97%.
« S CH,«S CH,
Ii / "Ii / "
O— PO— P
OCH5 OCH 5
C2H5 O — PC 2 H 5 O-P
Il \Il \
S OC2H5 S OC 2 H 5
Brechungsindex:«? = 1.5343. Ausbeute: 35% der Theorie.Refractive index: «? = 1.5343. Yield: 35% of theory.
Analyse für C11H2nN2O4P2S2 (Molgewicht 37iAnalysis for C 11 H 2n N 2 O 4 P 2 S 2 (molecular weight 37i
Berechnet ... N 7.57. P 16.76. S 17.29%: gefunden N 7.83. P 16.08. S 16.%",,Calculated ... N 7.57. P 16.76. S 17.29%: found N 7.83. P 08/16. S 16.% ",,
s cn,s cn,
II/' " ο—ρII / '"ο — ρ
Ο—PΟ — P
och.oh
OCH5 OCH 5
O OC2H5 O OC 2 H 5
Brechungsindex:»!6 = 1,5019. Ausbeute: 87.5% der Theorie.Refractive index: »! 6 = 1.5019. Yield: 87.5% of theory.
Analyse für C11H20N2OnP2S (Molgewicht 370):Analysis for C 11 H 20 N 2 O n P 2 S (molecular weight 370):
Berechnet ... N 7,56, P 16,75. S 8.65%; gefunden .... N 7,40, P 17,18. S 8.79%.Calculated ... N 7.56, P 16.75. S 8.65%; found .... N 7.40, P 17.18. S 8.79%.
1010
IlM.
Il
ilil
i;i;
o—O-
Ausbeute: 71% der Theorie. Analyse für C12H22N2O11P2S (Molgewicht 384):Yield: 71% of theory. Analysis for C 12 H 22 N 2 O 11 P 2 S (molecular weight 384):
Berechnet ... N 7,31 %: 20 gefunden .... N 7,84%.Calculated ... N 7.31%: 20 found .... N 7.84%.
Claims (1)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681670983 DE1670983C3 (en) | 1968-02-02 | 1968-02-02 | Pyridazinyl phosphorus (phosphonic) or thionophosphorus (phosphonic) acid esters, process for their preparation and their use |
| CH1922668A CH547313A (en) | 1968-02-02 | 1968-12-23 | PROCESS FOR THE PRODUCTION OF PHOSPHORUS-, PHOSPHONE-THIONPHOSPHORUS- OR THIONPHOSPHONIC ACID ESTERS OR ESTERAMIDES. |
| IL31318A IL31318A (en) | 1968-02-02 | 1968-12-24 | Phosphoric,phosphonic or thionophosphoric(-phosphonic)acid esters of pyridazinediol,their preparation and pest control compositions containing them |
| DK15469AA DK120707B (en) | 1968-02-02 | 1969-01-10 | Insecticidal and acaricidally active phosphoric, phosphonic or thionophosphoric (- phosphonic) - acid esters. |
| CS388A CS151500B2 (en) | 1968-02-02 | 1969-01-21 | |
| US793169*A US3547920A (en) | 1968-02-02 | 1969-01-22 | Phosphoric,phosphonic,thionophosphoric and thionophosphonic acid esters |
| GB1232564D GB1232564A (en) | 1968-02-02 | 1969-01-30 | |
| FR6902167A FR2001232A1 (en) | 1968-02-02 | 1969-01-31 | |
| NL6901586A NL6901586A (en) | 1968-02-02 | 1969-01-31 | |
| BE727723D BE727723A (en) | 1968-02-02 | 1969-01-31 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0054716 | 1968-02-02 | ||
| DE19681670983 DE1670983C3 (en) | 1968-02-02 | 1968-02-02 | Pyridazinyl phosphorus (phosphonic) or thionophosphorus (phosphonic) acid esters, process for their preparation and their use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1670983A1 DE1670983A1 (en) | 1971-04-01 |
| DE1670983B2 DE1670983B2 (en) | 1975-06-12 |
| DE1670983C3 true DE1670983C3 (en) | 1976-01-29 |
Family
ID=
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