GB814264A - New pesticidal basic esters of phosphorus-containing acids - Google Patents
New pesticidal basic esters of phosphorus-containing acidsInfo
- Publication number
- GB814264A GB814264A GB2833356A GB2833356A GB814264A GB 814264 A GB814264 A GB 814264A GB 2833356 A GB2833356 A GB 2833356A GB 2833356 A GB2833356 A GB 2833356A GB 814264 A GB814264 A GB 814264A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- diethyl
- benzyl
- phenylamino
- ethanol
- 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
- 239000002253 acid Substances 0.000 title abstract 3
- 230000000361 pesticidal effect Effects 0.000 title abstract 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title 1
- 150000007513 acids Chemical class 0.000 title 1
- 150000002148 esters Chemical class 0.000 title 1
- 229910052698 phosphorus Inorganic materials 0.000 title 1
- 239000011574 phosphorus Substances 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 15
- -1 alkyl radicals Chemical class 0.000 abstract 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 9
- 150000001875 compounds Chemical class 0.000 abstract 7
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000003118 aryl group Chemical group 0.000 abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 3
- 239000003513 alkali Substances 0.000 abstract 3
- 239000011230 binding agent Substances 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 229940126062 Compound A Drugs 0.000 abstract 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 abstract 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 abstract 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Substances 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 150000001342 alkaline earth metals Chemical group 0.000 abstract 2
- 150000005840 aryl radicals Chemical class 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 abstract 2
- RDYMFSUJUZBWLH-UHFFFAOYSA-N endosulfan Chemical class C12COS(=O)OCC2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl RDYMFSUJUZBWLH-UHFFFAOYSA-N 0.000 abstract 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 abstract 2
- 239000003701 inert diluent Substances 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 238000010992 reflux Methods 0.000 abstract 2
- 150000007944 thiolates Chemical class 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 abstract 1
- FOLYKNXDLNPWGC-UHFFFAOYSA-N 1-chloro-3-methoxypropan-2-ol Chemical compound COCC(O)CCl FOLYKNXDLNPWGC-UHFFFAOYSA-N 0.000 abstract 1
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 abstract 1
- XCEYKKJMLOFDSS-UHFFFAOYSA-N 4-chloro-n-methylaniline Chemical compound CNC1=CC=C(Cl)C=C1 XCEYKKJMLOFDSS-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- 229910020667 PBr3 Inorganic materials 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 abstract 1
- 239000004141 Sodium laurylsulphate Substances 0.000 abstract 1
- 239000000440 bentonite Substances 0.000 abstract 1
- 229910000278 bentonite Inorganic materials 0.000 abstract 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 abstract 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- KMJJJTCKNZYTEY-UHFFFAOYSA-N chloro-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(Cl)(=S)OCC KMJJJTCKNZYTEY-UHFFFAOYSA-N 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 229930003836 cresol Natural products 0.000 abstract 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 abstract 1
- LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 abstract 1
- PHHWLDOIMGFHOZ-UHFFFAOYSA-L disodium;dinaphthalen-1-ylmethanedisulfonate Chemical compound [Na+].[Na+].C1=CC=C2C(C(C=3C4=CC=CC=C4C=CC=3)(S(=O)(=O)[O-])S([O-])(=O)=O)=CC=CC2=C1 PHHWLDOIMGFHOZ-UHFFFAOYSA-L 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 239000003925 fat Substances 0.000 abstract 1
- 239000003292 glue Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 abstract 1
- 235000019341 magnesium sulphate Nutrition 0.000 abstract 1
- DWQGKMSNZGJKJS-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]ethanamine Chemical compound CCNCC1=CC=C(Cl)C=C1 DWQGKMSNZGJKJS-UHFFFAOYSA-N 0.000 abstract 1
- KEVOWRWHMCBERP-UHFFFAOYSA-N n-benzyl-4-methylaniline Chemical compound C1=CC(C)=CC=C1NCC1=CC=CC=C1 KEVOWRWHMCBERP-UHFFFAOYSA-N 0.000 abstract 1
- 239000012299 nitrogen atmosphere Substances 0.000 abstract 1
- 235000015097 nutrients Nutrition 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 150000003017 phosphorus Chemical class 0.000 abstract 1
- 150000003018 phosphorus compounds Chemical class 0.000 abstract 1
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 abstract 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 abstract 1
- 229940116357 potassium thiocyanate Drugs 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- YMPPRYJBYFNJTO-UHFFFAOYSA-M sodium;diethoxy-oxido-sulfanylidene-$l^{5}-phosphane Chemical compound [Na+].CCOP([O-])(=S)OCC YMPPRYJBYFNJTO-UHFFFAOYSA-M 0.000 abstract 1
- BYMVZHORNHZYPQ-UHFFFAOYSA-N sodium;diethyl phosphite Chemical compound [Na+].CCOP([O-])OCC BYMVZHORNHZYPQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000000375 suspending agent Substances 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 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
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
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)
Abstract
The invention comprises phosphorus compounds of formula A=P(OR)(OR1)-B-L-NR2R3 wherein A and B, which may be the same or different, represent oxygen or sulphur, R and R1 stand for like or unlike alkyl radicals, L represents a straight or branched chain aliphatic hydrocarbon radical which may be interrupted by an oxygen atom and R2 and R3, which may be the same or different, stand for alkyl, aryl or aralkyl radicals provided that R2 and R3 are not both alkyl or both aryl radicals. The aryl and aralkyl radicals may be substituted, e.g. by halogen, alkyl or alkoxy radicals. They may be prepared by reacting a compound A= P(OR)(OR1)-Y, where Y stands for halogen, either with a compound HBLNR2R3 in the presence of an acid-binding agent or with a compound MBLNR2R3, where M is a metal atom, such as an alkali or alkaline earth metal atom, preferably in an inert diluent such as benzene. Copper powder may be used as a catalyst. Suitable acid-binding agents include sodium carbonate or organic bases such as HBLNR2R3. When A and B are different, reaction below about 50 DEG C. gives the thionate isomer, whereas reaction at elevated temperatures, such as above about 110 DEG C., gives the thiolate isomer. This is also formed by heating the thionate form, e.g. above about 110 DEG C. Another method of preparation comprises reacting a compound A=P(OR)(OR1)-B-M1, where M1 is a metal atom, e.g. an alkali or alkaline earth metal atom or ammonium, with a compound YLNR2R3, preferably in an inert diluent such as benzene or ethanol. This method always gives the thiolate isomer, where A and B are different irrespective of the temperature. A further method of preparing compounds of formula O=P(OR)(OR1)-S-L-NR2R3 comprises reacting a compound M-O-P(OR)(OR1) with a compound NCS-L-NR2R3, preferably in an inert solvent. The products are pesticides (see Group VI). In examples: (1) sodium diethyl phosphite is prepared by the action of sodium on diethyl phosphite in benzene and reacted with N - ethyl - N - b - thiocyanoethyl - p - toluidine to give O,O1 - diethyl S - 2 - (N - ethyl - N - p - tolylamino) - ethyl phosphorothiolate; (2) N-b - bromoethyl - N - methyl - p - chloroaniline; (4) N,N - dibenzyl - b - chloroethylamine; (17) b - (N - benzyl - N - ethylamino) - ethyl bromide; and (23) b - (N - benzyl - N - phenylamino) - ethyl chloride are heated with sodium O,O1-diethyl phosphorothioate in ethanol or benzene to give O,O1-diethyl S - 2 - (N - methyl - N - p -chlorphenylamino) - ethyl phosphorothiolate, O,O1 - diethyl S-2-(N,N1-dibenzylamino) ethyl phosphorothiolate, O,O1-diethyl S-b -(N-benzylN-ethylamino) ethyl phosphorothiolate and O,O1 - diethyl S - b - (N - benzyl - N - phenylamino) ethyl phosphorothiolate respectively; (3) O,O1-diethyl S-1-(N-ethyl-N-phenylamino)-3-methoxyprop-2 -yl phosphorothiolothionate ; (5) O,O1-diethyl S-2-(N,N-dibenzylamino) ethyl phosphorothiolothionate; (10) O,O1-diethyl S-2-(N - benzyl - N - phenylamino) ethyl phosphorothiolate; (12) O,O1-diethyl S-2-(N-ethyl-N-phenylamino) ethyl phosphorothiolothionate; and (18) O,O1 - diethyl S - b - (N - benzyl - N - ethylamino) ethyl phosphorothiolothionate are prepared by adding O,O1-diethyl hydrogen phosphorothiolothionate to an ethanolic solution of sodium ethoxide and then refluxing with a - (N - ethyl - N - phenyl) amino - b - chloro - g - methoxypropane, N,N - dibenzyl - b - chloroethylamino hydrochloride, b - (N - benzyl - N - phenylamino) ethyl chloride hydrochloride, N-ethyl - N - b - chloroethylaniline and b -(N-benzyl-N-ethylamino)-ethyl chloride hydrochloride respectively; (6) O,O1 - diethyl - O11 - b - (N - methyl - N - phenylamino) ethyl phosphate; (8) O,O1 - diethyl O11 - b - (N - benzyl - N - phenylamino) ethyl phosphate; (19) O,O1 - diethyl O11 - b - (N - p - chlorobenzyl - N - ethylamino) ethyl phosphate; and (22) O,O1-diethyl S - b - (N - benzyl - N - phenylamino) ethyl phosphorothiolate are prepared by refluxing diethyl phosphorochloridate with the sodium salts (prepared by reaction of sodium metal with the compound) in benzene or toluene solution in a nitrogen atmosphere of b -(N-methyl-N-phenylamino) ethanol, b -(N-benzyl-N-phenylamino) ethanol, b - (N - p - chlorobenzyl - N - ethylamino) ethanol and b -(N-benzyl-N-phenylamino) ethyl mercaptan respectively; (7) O,O1 - diethyl S - b - (N - ethyl - N - phenylamino) ethyl phosphorothiolate; (9) O,O1-diethyl S - b - (N - benzyl - N - phenylamino) ethyl phosphorothiolate; (13) O,O1-diethyl S-2-(N - benzyl - N - p - methoxyphenylamino) ethyl phosphorothiolate; (16) O,O1-diethyl S - b - (N - phenyl - N - b 1 - phenylethylamino) ethyl phosphorothiolate; (20) O,O1-diethyl S - 1 - (N - methyl - N - phenylamino) - prop - 2 - yl phosphorothiolate; and (21) O,O1-diethyl S - b - (N - methyl - N - p - methoxyphenylamino) ethyl phosphorothiolate are prepared similarly from O,O1-diethyl phosphorochloridothionate and b - (N - ethyl - N - phenylamino) ethanol, b - (N - benzyl - N - phenylamino)-ethanol, b - (N - benzyl - N - p - methoxyphenylamino) ethanol, b - (N - phenyl - N - b 1 - phenylethylamino) ethanol, b - (N - methyl - N - phenylamino) isopropanol and N-methyl-N-b -hydroxyethyl-p-anisidine respectively; (15) O-ethyl - O1 - n - propyl phosphorochloridothionate is similarly reacted with b -(N-benzyl-N-p-tolylamino) ethanol to give O-ethyl-O1-n-propyl S - b - (N - benzyl - N - p - tolylamino) ethyl phosphorothiolate; (14) diethyl phosphorochloridothionate is reacted similarly but at 20-25 DEG C. with b -(N-benzyl-N-phenylamino)-ethanol sodium salt to give O,O1-diethyl-O11-b -(N-benzyl-N-phenylamino) ethyl phosphorothionate. Starting materials prepared are: N-ethyl-N-b -thiocyanoethyl-p-toluidine by interacting potassium thiocyanate and N-ethyl-N-b -bromoethyl-p-toluidine in acetone at about 20-25 DEG C.; N - b - bromoethyl - N - methyl - p - chloroaniline by interacting ethylene dibromide and N-methyl - p - chloroaniline; a - (N - ethyl - N - phenylamino) - b - chloro - g - methoxypropane by interacting thionyl chloride and the corresponding alcohol which may be obtained from N-ethylaniline and 1-chloro-3-methoxy-propan-2-ol; b - (N - benzyl - N - p - tolylamino) ethanol from N - benzyl - p - toluidine and ethylene chlorhydrin; b - (N - phenyl - N - b 1 - phenylethylamino) ethanol from b -hydroxyethylaniline and b -phenylethyl bromide; b -(N-benzyl-N-ethylamino) ethyl bromide from PBr3 and the corresponding alcohol; b - (N - benzyl - N - ethylamino) ethyl chloride hydrochloride from thionyl chloride and the corresponding alcohol; b -(N-p-chlorobenzyl-N-ethylamino)-ethanol from N-ethyl-p-chlorobenzylamine and ethylene chlorhydrin; b - (N - benzyl - N - phenylamino) ethyl mercaptan by reacting the corresponding chloride with thiourea and decomposing the resulting thiouronium salt with alkali.ALSO:Pesticidal compositions comprise phosphorus esters of formula A=P(OR)(OR1)-B-L-NR2R3 wherein A and B, which may be the same or different, stand for oxygen or sulphur, R and R1 stand for like or unlike alkyl radicals, L stands for a straight or branched chain aliphatic hydrocarbon radical which may be interrupted by an oxygen atom, and R2 and R3, which may be the same or different, stand for alkyl, aryl or aralkyl radicals provided that R2 and R3 are not both alkyl or both aryl radicals. The aryl and aralkyl radicals may be substituted, e.g. by halogen, alkyl or alkoxy radicals (for preparation see Group IV (b)). They may be used with carriers such as water, organic solvents, talc, chalk, kieselguhr or bentonite. Suspending or dispersing agents such as sodium dinaphthylmethane disulphonate or sodium lauryl sulphate, binders such as spindle oil, glycerol, wool fat, glue or resin, and plant nutrients such as urea and magnesium sulphate may also be present. In Example 11, a composition is prepared comprising O,O1-diethyl S-b -(N-benzyl-N-phenylamine) ethyl phosphorothiolate, diacetone alcohol, water and a condensation product of an alkyl cresol with ethylene oxide.
Publications (1)
Publication Number | Publication Date |
---|---|
GB814264A true GB814264A (en) | 1959-06-03 |
Family
ID=1741043
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2833356A Expired GB814264A (en) | 1956-09-17 | New pesticidal basic esters of phosphorus-containing acids |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB814264A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006060654A2 (en) * | 2004-12-01 | 2006-06-08 | Divergence, Inc. | Pesticidal compositions and methods |
CN112513056A (en) * | 2018-07-27 | 2021-03-16 | 上饶市康可得生物科技有限公司 | Preparation method of trimethyl ammonium ethyl phosphono diethyl iodide |
-
1956
- 1956-09-17 GB GB2833356A patent/GB814264A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006060654A2 (en) * | 2004-12-01 | 2006-06-08 | Divergence, Inc. | Pesticidal compositions and methods |
WO2006060654A3 (en) * | 2004-12-01 | 2006-12-14 | Divergence Inc | Pesticidal compositions and methods |
CN112513056A (en) * | 2018-07-27 | 2021-03-16 | 上饶市康可得生物科技有限公司 | Preparation method of trimethyl ammonium ethyl phosphono diethyl iodide |
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