CH526586A - Verfahren zur Herstellung neuer Thiophosphorsäureamidester - Google Patents
Verfahren zur Herstellung neuer ThiophosphorsäureamidesterInfo
- Publication number
- CH526586A CH526586A CH1564271A CH1564271A CH526586A CH 526586 A CH526586 A CH 526586A CH 1564271 A CH1564271 A CH 1564271A CH 1564271 A CH1564271 A CH 1564271A CH 526586 A CH526586 A CH 526586A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- general formula
- compound
- hydrogen
- formula iii
- Prior art date
Links
- -1 thio phosphoric acid imide esters Chemical class 0.000 title claims abstract description 10
- 230000002141 anti-parasite Effects 0.000 title abstract 2
- 239000003096 antiparasitic agent Substances 0.000 title abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 241000244206 Nematoda Species 0.000 claims description 7
- 239000000460 chlorine Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 241000238631 Hexapoda Species 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Chemical group 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- 230000001069 nematicidal effect Effects 0.000 abstract description 4
- 230000000895 acaricidal effect Effects 0.000 abstract description 3
- 239000000642 acaricide Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 239000005645 nematicide Substances 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000006378 damage Effects 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 230000000749 insecticidal effect Effects 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 241001425390 Aphis fabae Species 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 241001388466 Bruchus rufimanus Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 240000006677 Vicia faba Species 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical group C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 3
- 241000238876 Acari Species 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- 229910001369 Brass Inorganic materials 0.000 description 2
- 241000254000 Carausius morosus Species 0.000 description 2
- 241000122098 Ephestia kuehniella Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000244199 Panagrellus redivivus Species 0.000 description 2
- 241000253999 Phasmatodea Species 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 239000010951 brass Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 241001143309 Acanthoscelides obtectus Species 0.000 description 1
- 241000907225 Bruchidius Species 0.000 description 1
- 241000254001 Carausius Species 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 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
- 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
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 241000233835 Tradescantia Species 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 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
- 235000010633 broth Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- RJBIAAZJODIFHR-UHFFFAOYSA-N dihydroxy-imino-sulfanyl-$l^{5}-phosphane Chemical compound NP(O)(O)=S RJBIAAZJODIFHR-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- RDULEYWUGKOCMR-UHFFFAOYSA-N ethyl 2-chloro-3-oxobutanoate Chemical compound CCOC(=O)C(Cl)C(C)=O RDULEYWUGKOCMR-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000003031 feeding effect Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- WQYSXVGEZYESBR-UHFFFAOYSA-N thiophosphoryl chloride Chemical compound ClP(Cl)(Cl)=S WQYSXVGEZYESBR-UHFFFAOYSA-N 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
- 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
-
- 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
- C07F9/26—Amides of acids of phosphorus containing P-halide groups
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1564271A CH526586A (de) | 1969-07-18 | 1969-07-18 | Verfahren zur Herstellung neuer Thiophosphorsäureamidester |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1102869A CH526585A (de) | 1969-07-18 | 1969-07-18 | Verfahren zur Herstellung neuer Thiophosphorsäureamidester |
| CH1564271A CH526586A (de) | 1969-07-18 | 1969-07-18 | Verfahren zur Herstellung neuer Thiophosphorsäureamidester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH526586A true CH526586A (de) | 1972-08-15 |
Family
ID=4369307
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1564371A CH526587A (de) | 1969-07-18 | 1969-07-18 | Verfahren zur Herstellung neuer Thiophosphorsäureamidester |
| CH1564271A CH526586A (de) | 1969-07-18 | 1969-07-18 | Verfahren zur Herstellung neuer Thiophosphorsäureamidester |
| CH1102869A CH526585A (de) | 1969-07-18 | 1969-07-18 | Verfahren zur Herstellung neuer Thiophosphorsäureamidester |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1564371A CH526587A (de) | 1969-07-18 | 1969-07-18 | Verfahren zur Herstellung neuer Thiophosphorsäureamidester |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1102869A CH526585A (de) | 1969-07-18 | 1969-07-18 | Verfahren zur Herstellung neuer Thiophosphorsäureamidester |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS57131707A (xx) |
| AT (1) | AT315199B (xx) |
| CH (3) | CH526587A (xx) |
| CS (1) | CS199225B2 (xx) |
| PL (1) | PL81290B1 (xx) |
| SU (3) | SU497779A3 (xx) |
| TR (1) | TR17496A (xx) |
| ZA (1) | ZA704936B (xx) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8514853D0 (en) * | 1985-06-12 | 1985-07-17 | Sandoz Ltd | Controlling termites |
| JPH073627U (ja) * | 1992-07-07 | 1995-01-20 | 幸雄 中濱 | 医療ベッド用電動昇降機 |
-
1969
- 1969-07-18 CH CH1564371A patent/CH526587A/de not_active IP Right Cessation
- 1969-07-18 CH CH1564271A patent/CH526586A/de not_active IP Right Cessation
- 1969-07-18 CH CH1102869A patent/CH526585A/de not_active IP Right Cessation
-
1970
- 1970-07-16 CS CS705023A patent/CS199225B2/cs unknown
- 1970-07-16 SU SU1703109A patent/SU497779A3/ru active
- 1970-07-16 TR TR17496A patent/TR17496A/xx unknown
- 1970-07-16 PL PL1970142106A patent/PL81290B1/pl unknown
- 1970-07-16 SU SU1467354A patent/SU434637A3/ru active
- 1970-07-17 ZA ZA704936A patent/ZA704936B/xx unknown
- 1970-07-17 AT AT654170A patent/AT315199B/de not_active IP Right Cessation
-
1971
- 1971-10-04 SU SU1703106A patent/SU539531A3/ru active
-
1979
- 1979-09-17 JP JP54119986A patent/JPS57131707A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AT315199B (de) | 1974-05-10 |
| JPS57131707A (en) | 1982-08-14 |
| PL81290B1 (xx) | 1975-08-30 |
| SU497779A3 (ru) | 1975-12-30 |
| TR17496A (tr) | 1975-07-23 |
| CH526587A (de) | 1972-08-15 |
| CH526585A (de) | 1972-08-15 |
| ZA704936B (en) | 1972-02-23 |
| SU434637A3 (ru) | 1974-06-30 |
| SU539531A3 (ru) | 1976-12-15 |
| CS199225B2 (en) | 1980-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |