DE1793838C2 - 3-Isoxazolylthiono-phosphorsäure-(-phosphonsäure-Werivate und Verfahren zu ihrer Herstellung - Google Patents
3-Isoxazolylthiono-phosphorsäure-(-phosphonsäure-Werivate und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1793838C2 DE1793838C2 DE1793838A DE1793838A DE1793838C2 DE 1793838 C2 DE1793838 C2 DE 1793838C2 DE 1793838 A DE1793838 A DE 1793838A DE 1793838 A DE1793838 A DE 1793838A DE 1793838 C2 DE1793838 C2 DE 1793838C2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- isoxazolylthionophosphoric
- preparation
- bath temperature
- derivatives
- 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
- 238000000034 method Methods 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 3
- KWJDAFWWZNEPTO-UHFFFAOYSA-N dihydroxy-(1,2-oxazol-3-yloxy)-sulfanylidene-lambda5-phosphane Chemical compound C1=CON=C1OP(=S)(O)O KWJDAFWWZNEPTO-UHFFFAOYSA-N 0.000 title description 2
- 229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 4
- 150000003016 phosphoric acids Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 241000238631 Hexapoda Species 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- -1 methoxy, ethoxy Chemical group 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 3
- 241000254032 Acrididae Species 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical group 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 241000238876 Acari Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000002026 Apamea apamiformis Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- YOABUJDGQWJXAI-UHFFFAOYSA-N OP(O)(OC1=CC=NO1)=O Chemical class OP(O)(OC1=CC=NO1)=O YOABUJDGQWJXAI-UHFFFAOYSA-N 0.000 description 1
- JPVRYIILUJHBGO-UHFFFAOYSA-N P(O)(O)=O.O1N=C(C=C1)OP(O)(O)=S Chemical class P(O)(O)=O.O1N=C(C=C1)OP(O)(O)=S JPVRYIILUJHBGO-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000126 substance 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
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
- C07F9/653—Five-membered rings
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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
worin bedeuten:
Ri Methyl, Äthyl;
R2 Methoxy, Äihoxy oder Phenyl;
R3 Wasserstoff, Halogen oder Methyl und R4 Wasserstoff, Methyl oder Phenyl.
2. Verfahren zur Herstellung der Verbindungen nach Ansprach 1, dadurch gekennzeichnet, daß man
in an sich bekannter Weise eine Verbindung der Formel:
MO-C C-R,
Il Il ' ο
(ii)
worin M für Wasserstoff, Alkalimetall oder Ammonium steht, gegebenenfalls in Anwesenheit eines
säurebindenden Mittels, mit einer Verbindung der Formel:
R1O S
\ll
P-Cl
(Hl)
umsetzt
15
20
25 Aus der DT-PS 9106 52 sind insektizid wirkende
5-lsoxazolylphosphorsäurederivate bekannt Diese lassen
jedoch hinsichtlich ihrer Insektiziden Wirkung gegen eine Reihe von Schadinsekten erheblich zu
wünschen übrig.
Der Gegenstand der Erfindung ist demgegenüber in den Ansprüchen näher definiert
Es hat sich gezeigt, daß die 3-Isoxazolylthino-phosphorsäure-(-phosphorsäure-)derivate
gemäß der Erfindung als Insektizide gegen eine Reihe von Schadinsekten, wie Fliegen, Küchenschaben, Reiswürmer, Pflanzeninsekten,
Grashüpfer, Heuschrecken, Milben, Blattlause, hochwirksam und den aus der DT-PS 91 06 52
bekannten Verbindungen wirkungsmäßig überlegen sind.
Beim Verfahren zur Herstellung der 3-lsoxazolylthiono-phosphorsäure-(-phosphorsäure-)derivate
bedeutet in der Formel Il M z. B. ein Nailrium- oder Kaliumatom.
Als säurebindende Mittel kommen z. 3. Alkalimetallalkoholate, -hydroxide, -carbonate oder -bicarbonate
oder organische Basen in Betracht.
Das Verfahren gemäß der Erfindung läßt sich durch folgendes Reaktionsschema darstellen:
P-Cl + MO-C
/ Il
N (IU)
(H) R1O X
C-R3 » P-O-C C-R3
C-R3 » P-O-C C-R3
Il / Il Il
C-R4 R2 N C-R4
(D
Sofern von einer Verbindung der Formel (II) ausgegangen wird, in welcher M die Bedeutung von
Wasserstoff besitzt, sollte die Umsetzung in Gegenwart eines säurebindenden Mittels durchgeführt werden.
Beispiele für erfindungsgemäße 3-Isoxazolylthionophosphorsäure-(-phosphorsäure-)derivate
der Formel (I) sind:
3-Isoxazolylthiono-phosphorsäure(-phosphonsäurc-)derivate
0,0-Diäthyl-0-3-isoxazolylphosphorothioat 0,0-Diäthyl-0-(5-methyl-3-isoxazolyl)-phosphorothioat
O,O-Diäthyl-O-(5-methyl-3-isoxazolyl)-phosphorothioat
O.O-Dimcthyl-O-C'i-methyl-S-isoxa/olyn-phosphorothioat
O,O-Diiithyl-O-(4,5-dimethyl-3-isoxa/.olyl)-phosphomthioat
O1O-D iiithyl-O-(5-phcnyl-3-isox:i/olyl)-phosphorothioal
Kp. 90"C/0,2 mm Hg (Badtemperatur) Kp. 123 C/0,2mm Hg (Badtemperatur)
Kp. 120-123"C70,2mm Hg (Badtemperatur)
Kp. 120u(70,2 mm Hg (Badtemperatur)
Kp. 110 il70,2 mm Hg (Badtemperatur)
Kp. 160'(70,15 mm Hg (Badtemneratur)
Fortsetzung
7 0,0-Diäthyl-0-(5-methyl-4-brom-3-isoxazoIyl)- Kp. 153 °C/0,2 mm Kg (Badtemperatur)
phosphorothioat
8 0-Äthyl-0-(3-isoxazolyl)-phenylphosphorothioat Kp. 140°C/0,l mm Hg (Badtemperatur)
9 O-Athyl-O-{5-methyl-3-isoxazolyI-phenyiphosphorothioat Kp. 135-140°C/0,l mm Hg
(Badtemperatur)
10 O-Äthyl-O-(5-methy]-4-brom-3-isoxazolyl-phenyl- Kp. I3O-135°C/O,O5 mm Hg
phosphorothioat (Badtemperatur)
11 O-Äthyl-O-(4,5-dimethyl-3-isoxazolyl)-phenyl- Kp. 140°C/0,04 mm Hg
phosphorothioat (Badtemperatur)
12 O-Älhyl-CMS-phenylO-isoxazolyO-phenylphosphoro- gelbes Öl*)
thioat
13 O,O-Dimethyl-O-(5-phenyI-3-isoxazolyl)-phosphorothioat gelbes Öl*)
*) Nach Reinigung durch Silikagcl-Chromatographie lur die llemenUiranalysc.
Claims (1)
1. 3-IsoxazoIylthiono-phosphorsäure-(phosphorsäure-)derivate
der Formel:
R.o §
Ρ—Ο—C C-R3
Il Il
N. C-R4
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5083565 | 1965-08-20 | ||
| JP5414465 | 1965-09-04 | ||
| JP5553765 | 1965-09-11 | ||
| JP5602565 | 1965-09-13 | ||
| JP4320266 | 1966-07-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1793838B1 DE1793838B1 (de) | 1978-01-05 |
| DE1793838C2 true DE1793838C2 (de) | 1978-08-31 |
Family
ID=27522303
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1567137A Expired DE1567137C3 (de) | 1965-08-20 | 1966-08-19 | Insektizides Mittel auf der Basis von Phosphorsäureisoxazolyiestern |
| DE1793838A Expired DE1793838C2 (de) | 1965-08-20 | 1966-08-19 | 3-Isoxazolylthiono-phosphorsäure-(-phosphonsäure-Werivate und Verfahren zu ihrer Herstellung |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1567137A Expired DE1567137C3 (de) | 1965-08-20 | 1966-08-19 | Insektizides Mittel auf der Basis von Phosphorsäureisoxazolyiestern |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3759941A (de) |
| DE (2) | DE1567137C3 (de) |
| GB (1) | GB1115585A (de) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4094974A (en) * | 1977-02-24 | 1978-06-13 | Stauffer Chemical Company | Isoxazole phosphates and phosphonates |
| JPS6026119B2 (ja) * | 1977-06-09 | 1985-06-21 | 三共株式会社 | 有機リン酸エステル類およびそれを含有する殺虫殺ダニ剤 |
| US4380539A (en) * | 1981-03-11 | 1983-04-19 | E. I. Du Pont De Nemours And Company | Nematocidal composition containing O,O-diethyl O-(5-phenylisoxazol-3-yl)phosphorothioate and an ethanimidothioate |
| US6099850A (en) * | 1981-10-26 | 2000-08-08 | Battelle Memorial Institute | Termite and boring insect barrier for the protection of wooden structures |
| US6331308B1 (en) | 1981-10-26 | 2001-12-18 | Battelle Memorial Institute | Method and apparatus for providing long term protection from intrusion by insects and other cold blooded animals |
| US6060076A (en) * | 1981-10-26 | 2000-05-09 | Battelle Memorial Institute | Method and apparatus for providing long term protection from intrusion by insects and other cold blooded animals |
| US5925368A (en) * | 1981-10-26 | 1999-07-20 | Battelle Memorial Institute | Protection of wooden objects in direct contact with soil from pest invasion |
| FR2528665A1 (fr) * | 1982-06-21 | 1983-12-23 | Rhone Poulenc Agrochimie | Compositions insecticides et acaricides a base d'isoxathion et d'un pyrethroide et traitements phytosanitaires effectues au moyen de ces compositions |
| US6572872B2 (en) | 1989-09-01 | 2003-06-03 | Battelle Memorial Institute | Method and apparatus for providing long term protection from intrusion by insects and other cold blooded animals |
| US6319511B1 (en) | 1989-09-01 | 2001-11-20 | Battelle Memorial Institute | Termite and boring insect barrier for the protection of wooden structures |
| US6852328B1 (en) | 1989-09-01 | 2005-02-08 | Battelle Memorial Institute K1-53 | Method and device for protection of wooden objects proximate soil from pest invasion |
| US5856271A (en) * | 1995-06-07 | 1999-01-05 | Battelle Memorial Institute | Method of making controlled released devices |
| US5985304A (en) | 1998-02-25 | 1999-11-16 | Battelle Memorial Institute | Barrier preventing wood pest access to wooden structures |
| DE19953775A1 (de) | 1999-11-09 | 2001-05-10 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE10015310A1 (de) * | 2000-03-28 | 2001-10-04 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE10042736A1 (de) | 2000-08-31 | 2002-03-14 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE102007045955A1 (de) | 2007-09-26 | 2009-04-09 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| BRPI0924451B1 (pt) | 2009-03-25 | 2017-12-26 | Bayer Intellectual Property Gmbh | Combinations of active substances and their uses, as well as methods for the control of animal pests and method for the manufacture of insecticides and acaricides |
| CN113767924B (zh) * | 2021-08-13 | 2022-08-23 | 上海应用技术大学 | 异噁唑类化合物在杀虫剂中的应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA529113A (en) * | 1951-04-20 | 1956-08-14 | J. R. Geigy A.-G. | Phosphoric acid esters |
| BE589122A (de) * | 1959-03-28 | 1900-01-01 | ||
| FR1404889A (fr) * | 1963-08-13 | 1965-07-02 | Bayer Ag | Procédé de fabrication d'esters d'acides: phosphoriques, phosphoniques, phosphiniques, ou thionophosphoriques, thionophosphoniques, ou thionophosphiniques |
-
1966
- 1966-08-19 DE DE1567137A patent/DE1567137C3/de not_active Expired
- 1966-08-19 DE DE1793838A patent/DE1793838C2/de not_active Expired
- 1966-08-22 GB GB37608/66A patent/GB1115585A/en not_active Expired
-
1970
- 1970-05-05 US US00034867A patent/US3759941A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE1567137C3 (de) | 1979-01-25 |
| DE1567137A1 (de) | 1970-07-23 |
| US3759941A (en) | 1973-09-18 |
| DE1567137B2 (de) | 1978-05-03 |
| GB1115585A (en) | 1968-05-29 |
| DE1793838B1 (de) | 1978-01-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8328 | Change in the person/name/address of the agent |
Free format text: HENKEL, G., DR.PHIL. FEILER, L., DR.RER.NAT. HAENZEL, W., DIPL.-ING., PAT.-ANW., 8000 MUENCHEN |