PL101873B1 - A method of producing new estero-amides of phosphoric acids - Google Patents
A method of producing new estero-amides of phosphoric acids Download PDFInfo
- Publication number
- PL101873B1 PL101873B1 PL1976204562A PL20456276A PL101873B1 PL 101873 B1 PL101873 B1 PL 101873B1 PL 1976204562 A PL1976204562 A PL 1976204562A PL 20456276 A PL20456276 A PL 20456276A PL 101873 B1 PL101873 B1 PL 101873B1
- Authority
- PL
- Poland
- Prior art keywords
- radical
- carbon atoms
- methyl
- formula
- alkyl radical
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 150000003016 phosphoric acids Chemical class 0.000 title description 2
- -1 phosphoric acid ester amides Chemical class 0.000 claims description 31
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 239000011734 sodium Substances 0.000 claims description 11
- 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 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- QECVIPBZOPUTRD-UHFFFAOYSA-N N=S(=O)=O Chemical class N=S(=O)=O QECVIPBZOPUTRD-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 1
- 239000003701 inert diluent Substances 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 210000001699 lower leg Anatomy 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 159000000000 sodium salts Chemical class 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- YFAIEMNQOFRDEC-UHFFFAOYSA-N 1-chloro-n-methylmethanesulfonamide Chemical compound CNS(=O)(=O)CCl YFAIEMNQOFRDEC-UHFFFAOYSA-N 0.000 description 1
- XQJKFDKSLYEAAD-UHFFFAOYSA-N 2,5-dichloro-n-methylbenzenesulfonamide;sodium Chemical compound [Na].CNS(=O)(=O)C1=CC(Cl)=CC=C1Cl XQJKFDKSLYEAAD-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 101100231508 Caenorhabditis elegans ceh-5 gene Proteins 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- XLFFZTRASSYJRX-UHFFFAOYSA-N [Ni]C1=CC=CC=C1 Chemical compound [Ni]C1=CC=CC=C1 XLFFZTRASSYJRX-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000005998 bromoethyl group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-N disulfuric acid Chemical class OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- JPZKJABGOSPYDD-UHFFFAOYSA-N n-benzylmethanesulfonamide Chemical compound CS(=O)(=O)NCC1=CC=CC=C1 JPZKJABGOSPYDD-UHFFFAOYSA-N 0.000 description 1
- BCQYERJJTKTDOS-UHFFFAOYSA-N n-butylmethanesulfonamide;sodium Chemical compound [Na].CCCCNS(C)(=O)=O BCQYERJJTKTDOS-UHFFFAOYSA-N 0.000 description 1
- ARVFJXQBYGRUAE-UHFFFAOYSA-N n-methylbenzenesulfonamide;sodium Chemical compound [Na].CNS(=O)(=O)C1=CC=CC=C1 ARVFJXQBYGRUAE-UHFFFAOYSA-N 0.000 description 1
- MKSNNGCYPOHJFH-UHFFFAOYSA-N n-methylbutane-1-sulfonamide;sodium Chemical compound [Na].CCCCS(=O)(=O)NC MKSNNGCYPOHJFH-UHFFFAOYSA-N 0.000 description 1
- UHNHTTIUNATJKL-UHFFFAOYSA-N n-methylmethanesulfonamide Chemical compound CNS(C)(=O)=O UHNHTTIUNATJKL-UHFFFAOYSA-N 0.000 description 1
- AUSDMZUIKMAAEN-UHFFFAOYSA-N n-prop-2-enylbenzenesulfonamide Chemical compound C=CCNS(=O)(=O)C1=CC=CC=C1 AUSDMZUIKMAAEN-UHFFFAOYSA-N 0.000 description 1
- TYVZEADQWCCODY-UHFFFAOYSA-N n-prop-2-enylmethanesulfonamide Chemical compound CS(=O)(=O)NCC=C TYVZEADQWCCODY-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2479—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1)
- C07F9/2483—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1) containing the structure P(=X)n-N-S (X = O, S, Se; n = 0, 1)
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (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)
Description
Przedmiotem wynalazku jest sposób wytwarza¬
nia nowych estro-amidów kwasów fosforowych
o wzorze ogólnym 1, /w którym R1 oznacza rodnik
alkilowy lub etylowy, R2 oznacza rodnik alkilowy
o 1—6 atomach wegla, alkenylowy, aryloalkilowy
lub grupe o wzorze ogólnym 4, w którym A ozna¬
cza rodnik alkilowy o 1—6 atomach wegla lub
atom chlorowca i m oznacza liczbe 0, 1, 2 lub 3,
R3 oznacza rodnik alkilowy o 1—6 atomach wegla
ewentualnie podstawiony atomem chlorowca lub
oznacza grupe o wzorze ogólnym 5, w którym B
oznacza atom 'Chlorowca, rodnik alkilowy o 1—6
atomach, wegla, grupe nitrowa lub grupe alkoksy-.
Iowa o 1—6 atomach wegla, k oznacza liczbe 0, 1,
2 lub 3 i X oznacza atom tlenu lub siarki.
Nowe zwiazki o wzorze 1 maja bardzo dobre
dzialanie owadobójcze, roztoozobójcze, nicieniobój-
cze i wykazuja lepsza skutecznosc i szersze spek¬
trum dzialania niz zwiazki o podobnej budowie
chemicznej, zwlaszcza sa bardzo skuteczne na prze-
dziorkowate, które uodpornily sie na rózne znane
pestycydy fosforoorganiczne.
Korzystnie we wzorze 1, R2 oznacza rodnik alki¬
lowy o 1—4 atomach wegla, rodnik alkenylowy
taki jak rodnik winylowy, alilowy, propenylowy
i metalilowy, korzystnie alilowy, rodnik aryloalki¬
lowy zwlaszcza benzylowy i 2-fenyloetylowy, ko¬
rzystnie benzylowy, nie podstawiony rodnik feny¬
lowy lub rodnik fenyIowy zawierajacy 1—3,
zwlaszcza 1—2 podstawników,, takich jak atomy
2
chlorowców, rodniki alkilowe o 1—4 atomach
wegla, zwlaszcza metylowe i R3 oznacza rodnik
alkilowy o 1—4 atomach wegla, chlorowcowany
rodnik alkilowy o 1—4 atomach wegla, na przy¬
klad bromoetylowy, 2-chloroetylowy, 2-bromoetylo-
wy, 3-chloropropylowy, 3-chlorobutylowy, 4-chlo-
robutylowy, lnnietylo^-chloropropylowy, 1-metylo-
-3-chloropropylowy, 1-chilorometyloetylowy, 1-
chlorometylo-2-chloroetylowy, zwlaszcza chlorome-
tylowy, nie podstawiony rodnik fenylowy lub rod¬
nik fenylowy zawieraja-cy 1—3 podstawników, któ¬
re stanowia rodniki alkilowe o 1—4 atomach
wegla, zwlaszcza metylowe, atomy chlorowców,
zwlaszcza ichloru i bromu, grupy alkoksylowe
o 1—4 atomach wegla i grupy nitrowe.
Sposób wedlug wynalazku polega na tym, ze ha¬
logenki tio- lub dwutiofosforylu o wzorze ogólnym
2, w którym R1 i X maja wyzej podane znaczenie,
Hal oznacza atom chlorowca, poddaje sie reakcji
z sola sulfonyloamklu o wzorze ogólnym 3,
w którym R2 i R3 maja wyzej podane znaczenie
M2 oznacza atom metalu alkalicznego.
W stosowanych w sposobie wedlug wynalazku
zwiazkach o wzorze 2 i 3 Hal oznacza korzystnie
atom chloru, a M2 oznacza korzystnie atoim potasu
lub sodu.
Przykladami stosowanych halogenków (tio) lub
dwutiofosforylowych o wzorze 2 sa nastepujace
zwiazki: chlorek O-metylo-S-nnpropylotiofosfoicylu,
chlorek O-etylo-S-n-propylotiofosforylu, chlorek 0-
101 873101 873
3
^etylo-S-n-propylotiofosforylu i chlorek 0-etylo-S-
-^n-propylotiofosforylu i chlorek 0-etylonS-n-propy-
lotiofosforylu. ^
Przykladami soli sulfonamidów o wzorze 5 sa
nastepujace zwiazki:, sól sodowa N-metylometano-
suilfonoamidu, sól sodowa N-metyloetanosulfona-
midu, sól sodowa N-metylo-n-butanosulfonamidu,
sól sodowa N-metylobenzenosulfonamidu, sól sodo¬
wa N-metylo-4^hlorobenzenosulfonarciidu, sól I so¬
dowa N-metylo-2,5-dwuchlorobenzenosulfonamidu,
sól sodowa N-metylo-4-metoksybenzenosulfonanii-
du, sól sodowa N-(metylo-2-(metoksy-5-chlorobenize-
nosulfioinamidu, sól sodowa N-metylo-2-nitrobenze-
nosiulfonamddu, sól sodowa N-etylometanosulfona-
midu, sól sodowa N-izo-propylometanosulfonaimidu,
sól sodowa N-izo-propylobenzeno&ulfonamidu, sól
sodowa N-n-butylometanosulfonamidu, sól sodowa
N-alilometanosulfonamidu, sól #sodowa N-alilo-
benzenosulfonamidu, sól sodowa metanosulfon-
amidu, sól sodowa benzenosulfonilidu, sól so¬
dowa metanosulfono-4-chloroanilidu, sól sodowa
metanosulfono-4-metyiloaniilidu, sól sodowa me-
' tanosulfono-2-metylo-4-chloro-anilidu, sól so¬
dowa N^benzylometanosulfonamidu, sól sodowa
metanosulfono-N-2-metyloanilidu, sól metanosul-
fono-N-2,4-dwumetyloanilidu, sól sodowa me-
tanosulfono-N-2,4-dwuchloroanilidu, sól sodowa
metanosulfono-N-2-metylo-4-chloroanilidu, sól so¬
dowa N-metylochlorometanosulfonamidu, . sól
sodowa N-metylo-4-beomobenzenosulfonamidu i sól
sodowa N-metylo-2,4,5—trójchlorobenzenosulfona-
midu i odpowiednie sole potasowe.
Sposób wedlug wynalazku mozna przedstawic
schematami 1 i 2.
Sposób wedlug wynalazku prowadzi sie korzyst¬
nie w rozpuszczalniku lub rozcienczalniku. Jako
rozpuszczalniki stosuje sie na przyklad wode, obo¬
jetne rozpuszczalniki organiczne, takie jak alifa¬
tyczne, alieykliozne i aromatyczne weglowodory,
ewentualnie chlorowane, np. heksan, cykloheksan,
eter naftowy, ligroine, benzen, toluen, ksylen,
chlorek metylenu, chloroform czterochlorek wegla,
chlorek etylenu, trójchloroetylen i chlorobenzein,
etery, np eter etylowy, eter metyloetylowy, eter
izopropylowy, eter butylowy, tlenek propylenu,
dioksan i czterowodorofuran, ketony, np. aceton,
keton metylowoetylowy, metylowoizopropylowy
i metyilowoizobutylowy, mitryle, np. acetonitryl,
propionitryl i akrylonitryl, alkohole, np. metanol,
etanol, izopropynol, Il^rzed., butanoliiglikol, estry
np. octan etylu i octan amylu kwasów i sulfo-
tlenki, np. sulfotlenek dwumetylowy i zasady np.
pirydyne.
Sposób wedlug wynalazku mozna prowadzic
w szerokim zakresie temperatur. Na ogól proces
prowadzi sie w granicach od temperatury .—20°C
do temperatury wrzenia mieszaniiny, korzystnie
'w temperaturze 0—100°C.
Proces prowadzi sie korzystnie pod cisnieniem
atmosferycznym, chociaz mozna równiez stosowac
cisnienie podwyzszone i zmniejszone.
Nizej .podaje sie przyklady otrzymywania zwiaz¬
ków sposobem wedlug wynalazku.
Przyklad I. Dysperguje sie 21 g metanosulfo-
noanilidu sodu w 150 ml toluenu i dodaje sie 20 g
chloirku 0-etylOnS-n-propylotiofosforylu. Mieszanine
ogrzewa sie w temperaturze 80—90°C przez 3—4
godzimy do zakonczenia reakcji.
Po ustaleniu reakcji mieszanine reakcyjna chlo¬
dzi sde do temperatury pokojowej, przemywa woda
i l%wodnym roztworem wodorotlenku sodu, po¬
nownie woda. Mieszanine osusza sie za pomoca
bezwodnego siarczanu sodu. Z osuszonej miesza-*
niny reakcyjnej oddestylowuje sie toluen pod
zmniejszonym cisnieniem otrzymujac 25 g estru 0-
-etylo-S-n-propylowego kwasu N-fenykHN-meta-
nosulfonyloamidotiofosforowego o wzorze 6 w po¬
staci bezbarwnego oleju (n^0 = 1,5400)
Wedlug przykladów otrzymuje sie zwiazki ze¬
stawione w tablicy 1.
T a b 1 i c & 1
Zwiazki o wzorze"* 1
Przyklad
T
II
III
IV
V
(VI
VII
viii •
IX
-X
R1
2
C2H6
c2h5 y
CHg
C2H6
' c2n
C2H5
C2H5
C2Hs
c2h$
R2
3
CHg
CHg
CHg
CHg
CHg
CHg
CHg.
CHg
CHg
R3
4
C2HS
aa-C4H*
CeHe
C6HI5
2,5-Cl-C6H5
p-CH3-C6H4
p-OCH8-C6H4
p-OCHgmCl-C6H^
o-N02-C6H4
Wlasciwosc fizyczna
n *? = 1,4986
n^= 1,4952
,n g = 1,5245
n ^° = 1,5190
n £° = 1,5394
n *J = 1^350
n£°= 1,5556
n ^ = 1,557:2
.11^ = 1,5420101 873
.1
XI
XII
XJEEI
XIV
XV
XVI
XVII
XVII
XIX
1 xx
1 XXI
XXII
2
C2H5
C2H5
C2H5
C2H6
c2n
C2H6
C2I^5
C2H5
C2H,5
C2I^5
C2H5
C2H5
3
C2Hs
1-C3H3
i-C2H7
i-C3H7
m-C4H9
-CH2CH2=CH.2
-CH2CH2^Cxi2
C6H5
p-Cl-C6H6
p-CHjCgl^
2CH34C1-C6H3
-CH2-CgH5
4
CH*
CH.
CHaCl
Cfik
CH3
CH,
CgH5
CgHg
CH*
CI^
CH3
CH3
c.d. tablicy 1
1
n ^ = 1,4972
mg = 1,5010
mg =1,5009
n g = 1,5037
n g = 1,4898
mg = 1,5038
ng= 1,5404
mg = 1,5550
. mg = 1,5371
n g = 1,5367
mg =1,5380
n g = 1,5444
Przyklad II. Dysperguje sie 13,1 g 'soli sodo¬
wej N-metylometanosulfonamidu w 1Ó0 ml acetoni-
trylu. Dodaje sie 21,9 g chlorku 0-etylo-S-n-pro-
pylodwutiofosforylu, w temperaturze pokojowej
i stopniowo ogrzewajac mieszanine miesza sie przez
4 godziny w temperaturze 40—50°C. Po zakoncze¬
niu reakcji oddestylowuje sie acetonitryl, do pozo¬
stalosci dodaje sie toluen po czym mieszanine prze¬
mywa sie woda, 1%-owym wodnym roztworem wo¬
dorotlenku sodu i ponownie woda.
Po osuszeniu warstwy tbluenowej bezwodnym
siarczanem sodu, usuwa sie toluen pod zmniejszo¬
nym cisnieniem, usuwa sie przez kilka godzin
w temperaturze 70°C (1 mm Hg otrzymujac 22 g
estru 0-etylo-S-n-propylowego kwasu N-metylo-N-
-metanosulfonyloamidodwutiofosforowego o wzorze
7 w postaci bezbarwnego oleju (ng = 1,5295).
Wedlug przykladu XXIII otrzymuje sie zwiazek
o wzorze 1 podane w tablicy 2.
Zwiazki o wzorze 1
Przyklad
1
XXIV
XXV
XXVI
XXVII
XXVIII
XXIX
xxx-
XXXI
XXXII
XXXIII
XXXIV
xxxv
XXXVI
XXXVII
XXXVIII
XXXIX
XL
R1
2
C^Hg
C2H5
C2H5
C2H5
C2H5
C2H5
C2H5
C2H5
C2H5
CH3
C2H5
C2H5
C2H5
C2Hr
C2H5
C2H5
C2H6
R2
3
CHS
CH3
CII3
CHis
C2H5
l-C^Hy
-CH2GH= CHg
-Cj-H^OH ==(JH2
CeH5
CII3
O-CH3-C5H4
2,4^Cl-C6Hg
2,4-Cl-C6H8
2-CH3,4Cl-C6H8
CHS
CH^
CK3
R3
4
C2H5
C6H5
P-CI-C5H4
2,4-Cl-CeH3
CH3
CH3
CHS
C6H6
CH3
CH3
CH3
CH3
CH3
C6H$
CH2C1
pBr-C6H4
2,4,5-Cl-C6H2
Wlasciwosc fizyczna
|
n^J = 1,5214
mg = 1,5440
mg = 1,5535
n^J = 1,5735
mg = 1,5220
mg = 1,5060
mg = 1,5245
mg = 1,5410
ng = 1,5530
mg = 1,5030
ng = 1,5359
ng = 1,5300
ng = 1,5390
ng = 1,5429
mg = 1,5075
ng = 1,5532
tJtop. = 99—101101 873
Claims (3)
1. Sposób wytwarzania estro- amidów kwasów fosforowych o wzorze 1, w którym R1 oznacza rod¬ nik metylowy lub etylowy, R2 oznacza rodnik alki¬ lowy o 1—6 atomach wegla, rodnik alkenylowy, aryloalkilowy lub grupe o wzorze ogólnym 4, w którym A oznacza rodnik alkilowy o 1—6 ato¬ mach wegla lub atom chlorowca i m oiznacza liczbe 0, 1, 2 lub 3, a izwlaszcza R2 oznacza rodnik alki¬ lowy o 1—4 atomach wegla, rodnik alilowy, ben¬ zylowy, mepodstawiony rodnik fenylowy lub rod¬ nik fenyIowy jedno- lub idxwu-podstawiooiy atomem chloru i rodnikiem metylowym, R3 oznacza rodnik alkilowy o 1—6 atomach wegla ewentualnie pod¬ stawiony atomem chlorowca lub gupa o wzorze ogólnym 5, w którym B oznacza atom chlorowca, rodnik alkilowy o 1—6 atomach wegla, grupe mi¬ trowa lub alkoksylowa o 1—6 atomach wegla, i K oznacza liczbe 0, 1, 2 lub 3, a izwlaszcza R3 8 oznacza rodnik alkilowy o 1—4 atomach wegla i ohlorometylowy, niepodstawiony rodnik fenylowy lub rodnik fenylowy jedno- lub trój-podstawiony atomem chloru, bromu, rodnikiem metylowym, 5 grupa metyloksylowa lub nitrowa, X oznacza atom tlenu lub siarki, znamienny tym, ze halogenki tLo (dwutio)-fosforylu o wzorze ogólnym 2, w którym R1 i X maja znaczenie wyzej podane i Hal oznacza atom chlorowca, zwlaszcza chloru, poddaje sie re- 10 akcji z sola isulfonyloamidu o wzorze ogólnym 3, w którym R2 i R3 maja wyzej podane znaczenie i M2 oznacza atom metalu alkalicznego, zwlaszcza atom sodu lub potasu.
2. Sposób iwedlug zastrz. 1, znamienny tym, ze 15 reakcje prowadzi sie w temperaturze od —20° do temperatury wrzenia mieszaniny reakcyjnej, zwlasz¬ cza w temperaturze 0—100QC.
3. Sposób wedlug zatrz. 2, znamienny tym, ze reakcje prowadzi sie w srodowisku obojetnego roz- 20 puszczalnika lub rozcienczalnika.101 873 R O X \H P-M' CH3CH2CH2S FT \ 3 SD2R WZÓR r'q x \ll ,P - Hal s CHoCH^CH-3 WZÓR 2 ¦<2f m <$ B, R' 2 / scyr WZÓR 3 WZÓR U C,H,Ov O 2 5 \ll WZÓR 5 ff W P - N / \ ^HoCH^Cr>p S02CH3 WZÓR 6 ZM£> S 2 5\ll ,P CH. -N, / V CH3CH2CH2S S02CH3 WZÓR 7101 873 C H O O ChL 2H5°\|| / 3 P - Cl + (ULSOlN. / 2 5 2 \ CHCH^S Na C2H5°\i? /CH3 y~\ + Naa CH0CHXHJS 9CLCJ-L 3 2 2 2 2 5 SCHEMAT 1 C2H5\f ^ p-a + ch3so2nx CH CH2CH2S Na C2H5°X § ^ .P-N + NaCL CHoCH^CrUS SO^CrU SCHEMAT 2 LDA Nr 2 - Typo — zam. 191/79 — 95 egz. Cena zl 45.—
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50113705A JPS5238022A (en) | 1975-09-22 | 1975-09-22 | Insecticides, miticides, and nematocides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL101873B1 true PL101873B1 (pl) | 1979-02-28 |
Family
ID=14619069
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1976192532A PL101231B1 (pl) | 1975-09-22 | 1976-09-20 | Srodek owadobojczy,roztoczobojczy i nicieniobojczy |
| PL1976204563A PL101874B1 (pl) | 1975-09-22 | 1976-09-20 | A method of producing new estero-amides of phosphoric acids |
| PL1976204558A PL101863B1 (pl) | 1975-09-22 | 1976-09-20 | A method of producing a new salt of amidothiophosphoric acids |
| PL1976204562A PL101873B1 (pl) | 1975-09-22 | 1976-09-20 | A method of producing new estero-amides of phosphoric acids |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1976192532A PL101231B1 (pl) | 1975-09-22 | 1976-09-20 | Srodek owadobojczy,roztoczobojczy i nicieniobojczy |
| PL1976204563A PL101874B1 (pl) | 1975-09-22 | 1976-09-20 | A method of producing new estero-amides of phosphoric acids |
| PL1976204558A PL101863B1 (pl) | 1975-09-22 | 1976-09-20 | A method of producing a new salt of amidothiophosphoric acids |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4134979A (pl) |
| JP (1) | JPS5238022A (pl) |
| AR (1) | AR219286A1 (pl) |
| AT (1) | AT347181B (pl) |
| AU (1) | AU507454B2 (pl) |
| BE (1) | BE846423A (pl) |
| BG (1) | BG27530A3 (pl) |
| BR (1) | BR7606275A (pl) |
| CA (1) | CA1081247A (pl) |
| CH (1) | CH622678A5 (pl) |
| CS (1) | CS194778B2 (pl) |
| DD (1) | DD127419A5 (pl) |
| DE (1) | DE2642054A1 (pl) |
| DK (1) | DK140804B (pl) |
| EG (1) | EG12121A (pl) |
| ES (1) | ES451762A1 (pl) |
| FR (1) | FR2324641A1 (pl) |
| GB (1) | GB1527400A (pl) |
| IL (1) | IL50505A (pl) |
| NL (1) | NL7610487A (pl) |
| PH (1) | PH12930A (pl) |
| PL (4) | PL101231B1 (pl) |
| PT (1) | PT65613B (pl) |
| RO (1) | RO69679A (pl) |
| SE (1) | SE7610466L (pl) |
| SU (1) | SU609456A3 (pl) |
| TR (1) | TR19274A (pl) |
| ZA (1) | ZA765669B (pl) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS604839B2 (ja) * | 1976-09-20 | 1985-02-06 | 日本特殊農薬製造株式会社 | 有機リン酸アミドエステル，その製法及び殺虫，殺ダニもしくは殺センチュウ剤 |
| DE3112064A1 (de) * | 1981-03-27 | 1982-10-07 | Basf Ag, 6700 Ludwigshafen | N-sulfonylierte thiolphosphoresteramide, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von insektiziden, spinnmilben und nematoden |
| US4804654A (en) * | 1986-04-07 | 1989-02-14 | E. I. Du Pont De Nemours And Company | Certain N-(R-sulfonyl) phosphonamidothioates and dithioates |
| CN87103208A (zh) * | 1986-04-07 | 1988-08-17 | 国际壳牌研究有限公司 | 膦酰胺化合物 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3176600A (en) * | 1962-06-06 | 1965-04-06 | Tokar George | Cam controlled diaphragm and focus coaction |
| US3904710A (en) * | 1971-08-19 | 1975-09-09 | Exxon Research Engineering Co | Pesticidal O,S{40 -dialkyl S-phenylthioalkyl dithiophosphates and preparation thereof |
| US3917845A (en) * | 1973-03-27 | 1975-11-04 | Chevron Res | O,S-dihydrocarbyl-N-alkylthio- or N-arylthio phosphoroamidothioates as insecticides |
-
1975
- 1975-09-22 JP JP50113705A patent/JPS5238022A/ja active Granted
-
1976
- 1976-08-31 RO RO7687407A patent/RO69679A/ro unknown
- 1976-09-16 US US05/723,834 patent/US4134979A/en not_active Expired - Lifetime
- 1976-09-16 GB GB38383/76A patent/GB1527400A/en not_active Expired
- 1976-09-17 CH CH1183576A patent/CH622678A5/de not_active IP Right Cessation
- 1976-09-17 IL IL50505A patent/IL50505A/xx unknown
- 1976-09-17 PH PH18914A patent/PH12930A/en unknown
- 1976-09-17 BG BG7634226A patent/BG27530A3/xx unknown
- 1976-09-17 PT PT65613A patent/PT65613B/pt unknown
- 1976-09-17 CS CS766055A patent/CS194778B2/cs unknown
- 1976-09-18 DE DE19762642054 patent/DE2642054A1/de not_active Withdrawn
- 1976-09-18 EG EG569/76A patent/EG12121A/xx active
- 1976-09-20 PL PL1976192532A patent/PL101231B1/pl unknown
- 1976-09-20 AU AU17930/76A patent/AU507454B2/en not_active Expired
- 1976-09-20 PL PL1976204563A patent/PL101874B1/pl unknown
- 1976-09-20 SU SU762398006A patent/SU609456A3/ru active
- 1976-09-20 PL PL1976204558A patent/PL101863B1/pl unknown
- 1976-09-20 PL PL1976204562A patent/PL101873B1/pl unknown
- 1976-09-20 DD DD194869A patent/DD127419A5/xx unknown
- 1976-09-21 BR BR7606275A patent/BR7606275A/pt unknown
- 1976-09-21 CA CA261,684A patent/CA1081247A/en not_active Expired
- 1976-09-21 NL NL7610487A patent/NL7610487A/xx not_active Application Discontinuation
- 1976-09-21 AT AT699276A patent/AT347181B/de not_active IP Right Cessation
- 1976-09-21 SE SE7610466A patent/SE7610466L/xx unknown
- 1976-09-21 DK DK424776AA patent/DK140804B/da unknown
- 1976-09-21 ZA ZA765669A patent/ZA765669B/xx unknown
- 1976-09-21 TR TR19274A patent/TR19274A/xx unknown
- 1976-09-22 AR AR264800A patent/AR219286A1/es active
- 1976-09-22 BE BE170801A patent/BE846423A/xx unknown
- 1976-09-22 FR FR7628517A patent/FR2324641A1/fr active Granted
- 1976-09-22 ES ES451762A patent/ES451762A1/es not_active Expired
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