DE2133200C3 - Dichlorvinylthionophosphorsäureesteramide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide, Akarizide und Nematozide - Google Patents
Dichlorvinylthionophosphorsäureesteramide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide, Akarizide und NematozideInfo
- Publication number
- DE2133200C3 DE2133200C3 DE2133200A DE2133200A DE2133200C3 DE 2133200 C3 DE2133200 C3 DE 2133200C3 DE 2133200 A DE2133200 A DE 2133200A DE 2133200 A DE2133200 A DE 2133200A DE 2133200 C3 DE2133200 C3 DE 2133200C3
- Authority
- DE
- Germany
- Prior art keywords
- acid ester
- dichlorovinylthionophosphoric
- iso
- methyl
- ester amides
- 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 Dichlorovinylthionophosphoric acid ester amides Chemical class 0.000 title claims description 97
- 238000000034 method Methods 0.000 title description 5
- 230000000895 acaricidal effect Effects 0.000 title description 4
- 230000001069 nematicidal effect Effects 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000642 acaricide Substances 0.000 title 1
- 239000002917 insecticide Substances 0.000 title 1
- 239000005645 nematicide Substances 0.000 title 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 7
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- ZSSBYOXGEIGBLA-UHFFFAOYSA-N 3-phenylpropa-1,2-dienylbenzene Chemical group C=1C=CC=CC=1C=C=CC1=CC=CC=C1 ZSSBYOXGEIGBLA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 4
- 125000006226 butoxyethyl group Chemical group 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 4
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 4
- 230000000749 insecticidal effect Effects 0.000 description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 4
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 4
- 125000005999 2-bromoethyl group Chemical group 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 3
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 150000002440 hydroxy compounds Chemical class 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 3
- 125000003136 n-heptyl 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])* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 3
- 125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- MNRWIFMPVCLIDS-UHFFFAOYSA-N 2,2-dichloroethenyl dihydrogen phosphate Chemical compound OP(O)(=O)OC=C(Cl)Cl MNRWIFMPVCLIDS-UHFFFAOYSA-N 0.000 description 1
- NYTPAANIMXKHJA-UHFFFAOYSA-N 2-methylprop-1-en-1-amine Chemical compound CC(C)=CN NYTPAANIMXKHJA-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 241000341511 Nematodes Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- KRCWTDLNIQKGJM-UHFFFAOYSA-N [P].S(=O)(=O)(Cl)Cl Chemical compound [P].S(=O)(=O)(Cl)Cl KRCWTDLNIQKGJM-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N methyl iso-propyl ketone Natural products CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- QROGIFZRVHSFLM-UHFFFAOYSA-N prop-1-enylbenzene Chemical group CC=CC1=CC=CC=C1 QROGIFZRVHSFLM-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008096 xylene 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/20—Esters of thiophosphoric acids containing P-halide groups
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2412—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of unsaturated acyclic alcohols
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)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE785787D BE785787A (fr) | 1971-07-03 | Nouveaux esteramides dichlorovinyliques d'acide thionophosphorique, leur procede de preparation et leur application comme insecticides, acaricides et nematicides | |
| DE2133200A DE2133200C3 (de) | 1971-07-03 | 1971-07-03 | Dichlorvinylthionophosphorsäureesteramide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide, Akarizide und Nematozide |
| BR4250/72A BR7204250D0 (pt) | 1971-07-03 | 1972-06-29 | E nematicidas a base destes processo para a obtencao de amidas de esteres de acido dicloroviniltiofosforico e composicoes inseticidas acaricida |
| IL7239801A IL39801A (en) | 1971-07-03 | 1972-06-30 | Thionophosphoric acid ester amides,their preparation and their use as insecticides,acaricides and nematocides |
| AU44112/72A AU462759B2 (en) | 1971-07-03 | 1972-06-30 | Novel thionophosphoric acid ester amides and their use as insecticides, acaricides and nematocides |
| NL7209217A NL7209217A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-07-03 | 1972-06-30 | |
| CH988972A CH534700A (de) | 1971-07-03 | 1972-06-30 | Verfahren zur Herstellung von Dichlorvinylthionophosphorsäureesteramiden |
| ES404468A ES404468A1 (es) | 1971-07-03 | 1972-07-01 | Procedimiento para la obtencion de amidas de esteres de a- cidos dicloroviniltionofosforicos. |
| IT26521/72A IT962349B (it) | 1971-07-03 | 1972-07-01 | Dicloroviniltionofosforesteramidi procedimento per la loro prepara zione e loro impiego come insetti cidi acaricidi e nematocidi |
| TR16932A TR16932A (tr) | 1971-07-03 | 1972-07-03 | Dikloroviniltionofosforik asid ester amidleri,bunlarin imaline mahsus usuller ve bunlarin insektisid,akarisid ve nematisid olarak kullanilmalari |
| ZA724541A ZA724541B (en) | 1971-07-03 | 1972-07-03 | Novel thionphosphoric acid ester amides and their use as insecticides acaricides and nematocides |
| FR7223951A FR2144729B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-07-03 | 1972-07-03 | |
| GB3095672A GB1348365A (en) | 1971-07-03 | 1972-07-03 | Thionophosphoric acid ester amides and their use as insecticides acaricides and nematocides |
| US510835A US3917754A (en) | 1971-07-03 | 1974-09-30 | Dichlorovinylthionophosphoric acid ester amides |
| US05/510,836 US4013795A (en) | 1971-07-03 | 1974-09-30 | Combating pests with dichlorovinylthionophosphoric acid ester amides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2133200A DE2133200C3 (de) | 1971-07-03 | 1971-07-03 | Dichlorvinylthionophosphorsäureesteramide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide, Akarizide und Nematozide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2133200A1 DE2133200A1 (de) | 1973-01-11 |
| DE2133200B2 DE2133200B2 (de) | 1979-05-17 |
| DE2133200C3 true DE2133200C3 (de) | 1980-01-10 |
Family
ID=5812610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2133200A Expired DE2133200C3 (de) | 1971-07-03 | 1971-07-03 | Dichlorvinylthionophosphorsäureesteramide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide, Akarizide und Nematozide |
Country Status (13)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE794293A (fr) * | 1972-01-21 | 1973-07-19 | Bayer Ag | Nouveaux diesteramides d'acide dichlorovinylthionophosphorique, leur procede de preparation et leur application comme insecticides et acaricides |
-
0
- BE BE785787D patent/BE785787A/xx unknown
-
1971
- 1971-07-03 DE DE2133200A patent/DE2133200C3/de not_active Expired
-
1972
- 1972-06-29 BR BR4250/72A patent/BR7204250D0/pt unknown
- 1972-06-30 NL NL7209217A patent/NL7209217A/xx not_active Application Discontinuation
- 1972-06-30 AU AU44112/72A patent/AU462759B2/en not_active Expired
- 1972-06-30 IL IL7239801A patent/IL39801A/xx unknown
- 1972-06-30 CH CH988972A patent/CH534700A/de not_active IP Right Cessation
- 1972-07-01 ES ES404468A patent/ES404468A1/es not_active Expired
- 1972-07-01 IT IT26521/72A patent/IT962349B/it active
- 1972-07-03 ZA ZA724541A patent/ZA724541B/xx unknown
- 1972-07-03 GB GB3095672A patent/GB1348365A/en not_active Expired
- 1972-07-03 TR TR16932A patent/TR16932A/xx unknown
- 1972-07-03 FR FR7223951A patent/FR2144729B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BR7204250D0 (pt) | 1974-10-22 |
| BE785787A (fr) | 1973-01-03 |
| AU462759B2 (en) | 1975-07-03 |
| ZA724541B (en) | 1973-03-28 |
| GB1348365A (en) | 1974-03-13 |
| ES404468A1 (es) | 1975-06-01 |
| NL7209217A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-01-05 |
| DE2133200A1 (de) | 1973-01-11 |
| IL39801A (en) | 1975-06-25 |
| IT962349B (it) | 1973-12-20 |
| CH534700A (de) | 1973-03-15 |
| TR16932A (tr) | 1973-11-01 |
| DE2133200B2 (de) | 1979-05-17 |
| FR2144729A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-02-16 |
| FR2144729B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-08-06 |
| AU4411272A (en) | 1974-01-03 |
| IL39801A0 (en) | 1972-08-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EHV | Ceased/renunciation |