AT219618B - Process for the production of new phosphoric acid amides or thiophosphoric acid amides - Google Patents
Process for the production of new phosphoric acid amides or thiophosphoric acid amidesInfo
- Publication number
- AT219618B AT219618B AT134160A AT134160A AT219618B AT 219618 B AT219618 B AT 219618B AT 134160 A AT134160 A AT 134160A AT 134160 A AT134160 A AT 134160A AT 219618 B AT219618 B AT 219618B
- Authority
- AT
- Austria
- Prior art keywords
- sep
- acid amides
- oxygen
- sulfur
- production
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000003578 thiophosphoric acid amides Chemical class 0.000 title description 3
- 150000003012 phosphoric acid amides Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000005265 dialkylamine group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229910019142 PO4 Inorganic materials 0.000 description 9
- 239000010452 phosphate Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- MJKVTPMWOKAVMS-UHFFFAOYSA-N 3-hydroxy-1-benzopyran-2-one Chemical compound C1=CC=C2OC(=O)C(O)=CC2=C1 MJKVTPMWOKAVMS-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical compound O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- PEQJBOMPGWYIRO-UHFFFAOYSA-N n-ethyl-3,4-dimethoxyaniline Chemical compound CCNC1=CC=C(OC)C(OC)=C1 PEQJBOMPGWYIRO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- -1 phosphoryl halide Chemical class 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/6552—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/6552—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring
- C07F9/65522—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring condensed with carbocyclic rings or carbocyclic ring systems
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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Herstellung von neuen Phosphorsäure- bzw.
Thiophosphorsäureamiden
In der niederländischen Patentschrift Nr. 86689 wird unter anderem die Herstellung von phosphorsauren und thionophosphorsauren Estern von Abkömmlingen von Pyron-und Tetronsäure angegeben, welche Ester zur Bekämpfung von Schädlingen zu verwenden sind.
Weiter ist beschrieben, dass man durch Reaktion eines Phosphorylhalogenids oder eines N-Alkyldi- amidophosphory1chlorids mit einem Metallsalz einer hydroxylierten aromatischen ringstickstoffhaltigen Verbindung Verbindungen herstellen kann, welche insektizide Wirkung haben. Mit Namen sind nur Bis (N, N-dimethylamido)- 8-hydroxychinolylphosphat und Bis (N, N-dimethylamido)-2-hydroxypyridylphos- phat genannt worden. Besonders die Abkömmlinge von Hydroxychinolin und insbesondere von 8-Hydroxychinolin haben eine stark insektizide Wirkung.
Von Bis (N, N-dimethylamido) -2-hydroxychinolylphosphat wurde jedoch ausgeführt, dass diese Verbindung keine physiologische Wirkung aufweist und namentlich keine Kontaktwirkung gegenüber normalen Blattläusen.
Gegenstand der Erfindung ist nun ein Verfahren zur Herstellung von neuen Phosphorsäure-bzw. Thio- phosphorsäureamiden der allgemeinen Formel
EMI1.1
in welcher Q der Rest einer Verbindung mit ringsauerstoffhaltigem heterocyclischem Kern ist, von dem eines der Kohlenstoffatome ein doppeltgebundenes Sauerstoffatom aufweist, X und X Sauerstoff oder Schwefel und R, R, R und R niedrige Alkylgruppen darstellen und X an ein Kohlenstoffatom des heterocyclischen Kernes von Q gebunden ist.
Der heterocyclische Kern von Q kann z. B. durch Alkyl- und Alkoxygruppen substituiert sein oder mit einem substituierten oder nicht substituierten Benzolring einen Teil eines kondensierten Ringsystems bil-
EMI1.2
Q kann den Rest von substituierter oder nicht substituierterTetronsäure, 1, 2-Pyron, 1, 4-Benzopyron, 1, 2-Benzopyron und 2, 3-Benzopyron sein. Besonders wenn Q den Rest eines 1, 4-Pyrons bezeichnet und besonders wenn dieser durch niedrige Alkylreste und niedrige Alkoxygruppen substituiert ist, kann man Verbindungen mit einer guten Wirkung gegen Schimmel erhalten. So hat z. B.
Bis (N, N-dimethylamido)- -O-(2-äthoxy-3,5-dimethyl-1,4-pyronyl)-6-phosphat in Versuchen mit Gerstenmehltau eine Kontakt-
<Desc/Clms Page number 2>
wirkung gezeigt, die zehnmal grösser als die des 2, 4-Dinitro-6- (l'-methylheptyl)-l-phenylkrotonats ist.
Die Herstellung der erfindungsgemäss erhältlichen Verbindungen kann derart durchgeführt werden, dass der Amidophosphorylrest oder der Amidothionophosphorylrest in einem Arbeitsgang eingeführt wird oder derart, dass dies in zwei Reaktionsstufen stattfindet. Bei diesem Verfahren lässt man die Verbindung Q-X-H, vorzugsweise in Anwesenheit eines halogenwasserstoffsäurebindenden Mittels, oder die Verbindung Q-X-Me, in welchen Formeln Q und Xi die obenerwähnte Bedeutung haben und Me ein Metall- atom, vorzugsweise Natrium oder Kalium, bezeichnet, mit einer Verbindung der allgemeinen Formel
EMI2.1
EMI2.2
EMI2.3
EMI2.4
<Desc/Clms Page number 3>
YTabehe II gibt hinter der betreffenden Nummer des Beispiels den Namen der dabei erhaltenen Verbindung an ; sie enthält in den zusätzlichen Beispielen 6 und 7 auch S-haltige Verbindungen.
Tabelle I
EMI3.1
<tb>
<tb> Beispiel <SEP> Ausgangsstoffe <SEP> Verdünnungs- <SEP> Reaktions- <SEP> Ausbeute <SEP> physikalische
<tb> mittel <SEP> Temperatur C <SEP> in% <SEP> Konstanten
<tb> 1 <SEP> 2-Äthoxy-3,5-dimethyl- <SEP> Tolüol <SEP> zirka <SEP> 110 <SEP> 84 <SEP> Fp=66-68 C
<tb> - <SEP> 6-hydroxy-l, <SEP> 4-pyron <SEP>
<tb> 2 <SEP> 2-Methoxy-3, <SEP> 5-dimethyl- <SEP> Toluol <SEP> zirka <SEP> 110 <SEP> 44 <SEP> Öl
<tb> - <SEP> 6-hydroxy-1, <SEP> 4-pyron <SEP>
<tb> 3 <SEP> 2- <SEP> Methyl- <SEP> 6-hydroxy- <SEP> Toluol <SEP> zirka <SEP> 110 <SEP> 36 <SEP> öl
<tb> -1,
4-pyro
<tb> 4 <SEP> a-Methyltetronsäure <SEP> Toluol <SEP> zirka <SEP> 110 <SEP> 31 <SEP> Fp <SEP> = <SEP> 42-48 C
<tb> 5 <SEP> 4- <SEP> Hydroxycumarin <SEP> Pyridin <SEP> zirka <SEP> 110 <SEP> 83 <SEP> Fp <SEP> = <SEP> 65-67 C
<tb>
EMI3.2
EMI3.3
<tb>
<tb> Tabelle <SEP> II
<tb> Beispiel <SEP> Rrodukt
<tb> 1 <SEP> Bis <SEP> (N, <SEP> N-dimethylamido)-O-(2-äthoxy-3,5-dimethyl-1,4-pyronyl)-6-phosphat
<tb> 2 <SEP> bis(N,N-dimethylamido)-O-(2-methoxy-3,5-dimethyl-1,4-pyronyl)-6-phosphat
<tb> 3 <SEP> Bis <SEP> (N, <SEP> N-dimethylamido)-0- <SEP> (2-methyl-l, <SEP> 4-pyronyl)-6-phosphat <SEP>
<tb> 4 <SEP> Bis(N,N-dimethylamido)-O-(2-dero-3-methyl-2,5-dihydrofuranyl)-4-phosphat
<tb> 5 <SEP> Bis(N,N-dimethylamido)-O-cumarinyl-4-phosphat
<tb> 6 <SEP> Bis <SEP> (N, <SEP> N-dimethylamido) <SEP> (2-äthoxy-3,5-dimethyl-1,4-pyronyl)-6-phosphat
<tb> 7 <SEP> Bis <SEP> (N,
N-dimethylamido)-s-(a-äthoxy-3,5-dimethyl-1,4-pyronyl)-6-thionophosphat
<tb>
EMI3.4
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the production of new phosphoric acid resp.
Thiophosphoric acid amides
In the Dutch patent specification No. 86689, inter alia, the production of phosphoric acid and thionophosphoric acid esters of derivatives of pyronic and tetronic acid is indicated, which esters are to be used for controlling pests.
It is also described that by reacting a phosphoryl halide or an N-alkyldiamidophosphoryl chloride with a metal salt of a hydroxylated aromatic compound containing ring nitrogen, compounds can be produced which have an insecticidal effect. Only bis (N, N-dimethylamido) - 8-hydroxyquinolyl phosphate and bis (N, N-dimethylamido) -2-hydroxypyridyl phosphate have been named. The derivatives of hydroxyquinoline and in particular of 8-hydroxyquinoline have a strong insecticidal effect.
For bis (N, N-dimethylamido) -2-hydroxyquinolyl phosphate, however, it was stated that this compound has no physiological effect and specifically no contact effect against normal aphids.
The invention now relates to a process for the production of new phosphoric acid or. Thiophosphoric acid amides of the general formula
EMI1.1
in which Q is the remainder of a compound with a ring oxygen-containing heterocyclic nucleus, one of the carbon atoms having a double-bonded oxygen atom, X and X being oxygen or sulfur and R, R, R and R being lower alkyl groups and X to a carbon atom of the heterocyclic nucleus of Q is bound.
The heterocyclic nucleus of Q can e.g. B. be substituted by alkyl and alkoxy groups or form part of a condensed ring system with a substituted or unsubstituted benzene ring
EMI1.2
Q can be the radical of substituted or unsubstituted tetronic acid, 1,2-pyrone, 1,4-benzopyrone, 1,2-benzopyrone and 2,3-benzopyrone. Particularly if Q denotes the radical of a 1,4-pyron and especially if this is substituted by lower alkyl radicals and lower alkoxy groups, compounds with a good effect against mold can be obtained. So has z. B.
Bis (N, N-dimethylamido) - -O- (2-ethoxy-3,5-dimethyl-1,4-pyronyl) -6-phosphate in experiments with barley powdery mildew a contact
<Desc / Clms Page number 2>
Effect shown that is ten times greater than that of 2,4-dinitro-6- (l'-methylheptyl) -l-phenylcrotonate.
The compounds obtainable according to the invention can be prepared in such a way that the amidophosphoryl radical or the amidothionophosphoryl radical is introduced in one operation or in such a way that this takes place in two reaction stages. In this process, the compound QXH, preferably in the presence of a hydrohalic acid binding agent, or the compound QX-Me, in which formulas Q and Xi have the meaning mentioned above and Me denotes a metal atom, preferably sodium or potassium, is left with a compound the general formula
EMI2.1
EMI2.2
EMI2.3
EMI2.4
<Desc / Clms Page number 3>
YTabehe II gives the name of the compound obtained after the relevant number of the example; in the additional examples 6 and 7 it also contains S-containing compounds.
Table I.
EMI3.1
<tb>
<tb> Example <SEP> Starting materials <SEP> Dilution <SEP> Reaction <SEP> Yield <SEP> physical
<tb> medium <SEP> temperature C <SEP> in% <SEP> constants
<tb> 1 <SEP> 2-ethoxy-3,5-dimethyl- <SEP> toluene <SEP> approx. <SEP> 110 <SEP> 84 <SEP> mp = 66-68 ° C
<tb> - <SEP> 6-hydroxy-l, <SEP> 4-pyrone <SEP>
<tb> 2 <SEP> 2-methoxy-3, <SEP> 5-dimethyl- <SEP> toluene <SEP> approx. <SEP> 110 <SEP> 44 <SEP> oil
<tb> - <SEP> 6-hydroxy-1, <SEP> 4-pyrone <SEP>
<tb> 3 <SEP> 2- <SEP> methyl- <SEP> 6-hydroxy- <SEP> toluene <SEP> approx. <SEP> 110 <SEP> 36 <SEP> oil
<tb> -1,
4-pyro
<tb> 4 <SEP> a-methyltetronic acid <SEP> toluene <SEP> approx. <SEP> 110 <SEP> 31 <SEP> Fp <SEP> = <SEP> 42-48 C
<tb> 5 <SEP> 4- <SEP> Hydroxycoumarin <SEP> Pyridine <SEP> approx. <SEP> 110 <SEP> 83 <SEP> Fp <SEP> = <SEP> 65-67 C
<tb>
EMI3.2
EMI3.3
<tb>
<tb> Table <SEP> II
<tb> Example <SEP> product
<tb> 1 <SEP> bis <SEP> (N, <SEP> N-dimethylamido) -O- (2-ethoxy-3,5-dimethyl-1,4-pyronyl) -6-phosphate
<tb> 2 <SEP> bis (N, N-dimethylamido) -O- (2-methoxy-3,5-dimethyl-1,4-pyronyl) -6-phosphate
<tb> 3 <SEP> to <SEP> (N, <SEP> N-dimethylamido) -0- <SEP> (2-methyl-l, <SEP> 4-pyronyl) -6-phosphate <SEP>
<tb> 4 <SEP> bis (N, N-dimethylamido) -O- (2-dero-3-methyl-2,5-dihydrofuranyl) -4-phosphate
<tb> 5 <SEP> bis (N, N-dimethylamido) -O-coumarinyl-4-phosphate
<tb> 6 <SEP> to <SEP> (N, <SEP> N-dimethylamido) <SEP> (2-ethoxy-3,5-dimethyl-1,4-pyronyl) -6-phosphate
<tb> 7 <SEP> to <SEP> (N,
N-dimethylamido) - (a-ethoxy-3,5-dimethyl-1,4-pyronyl) -6-thionophosphate
<tb>
EMI3.4
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL236443 | 1959-02-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT219618B true AT219618B (en) | 1962-02-12 |
Family
ID=19751587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT134160A AT219618B (en) | 1959-02-23 | 1960-02-22 | Process for the production of new phosphoric acid amides or thiophosphoric acid amides |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT219618B (en) |
| BE (1) | BE587903A (en) |
| CH (1) | CH411453A (en) |
| DK (1) | DK96092C (en) |
| FR (1) | FR1288728A (en) |
| GB (1) | GB947156A (en) |
-
1960
- 1960-02-19 GB GB597460A patent/GB947156A/en not_active Expired
- 1960-02-20 DK DK65560A patent/DK96092C/en active
- 1960-02-20 CH CH189660A patent/CH411453A/en unknown
- 1960-02-22 AT AT134160A patent/AT219618B/en active
- 1960-02-22 BE BE587903A patent/BE587903A/en unknown
- 1960-02-23 FR FR819253A patent/FR1288728A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK96092C (en) | 1963-05-27 |
| BE587903A (en) | 1960-08-22 |
| FR1288728A (en) | 1962-03-30 |
| CH411453A (en) | 1966-04-15 |
| GB947156A (en) | 1964-01-22 |
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