US3463839A - Alpha-haloalkyl phosphonothioates - Google Patents
Alpha-haloalkyl phosphonothioates Download PDFInfo
- Publication number
- US3463839A US3463839A US701795A US3463839DA US3463839A US 3463839 A US3463839 A US 3463839A US 701795 A US701795 A US 701795A US 3463839D A US3463839D A US 3463839DA US 3463839 A US3463839 A US 3463839A
- Authority
- US
- United States
- Prior art keywords
- ethyl
- methyl
- chloro
- sodium
- carbon atoms
- 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 - Lifetime
Links
- 125000004432 carbon atom Chemical group C* 0.000 description 31
- 125000000217 alkyl group Chemical group 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 18
- -1 trichlorophenyl Chemical group 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 12
- 239000000203 mixture Substances 0.000 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 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000004009 herbicide Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 5
- 235000013312 flour Nutrition 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XNEARKLZHZRZQE-UHFFFAOYSA-N P(O)(Cl)=S Chemical compound P(O)(Cl)=S XNEARKLZHZRZQE-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000000068 chlorophenyl group Chemical group 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000002363 herbicidal effect Effects 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 229950005499 carbon tetrachloride Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229940051043 cresylate Drugs 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000006501 nitrophenyl group Chemical group 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 2
- ZRKMQKLGEQPLNS-UHFFFAOYSA-N 1-Pentanethiol Chemical compound CCCCCS ZRKMQKLGEQPLNS-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 125000004965 chloroalkyl group Chemical group 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 125000004188 dichlorophenyl group Chemical group 0.000 description 2
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 125000005059 halophenyl group Chemical group 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
- 229940031826 phenolate Drugs 0.000 description 2
- 150000003018 phosphorus compounds Chemical class 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YNMZZHPSYMOGCI-UHFFFAOYSA-N undecan-3-one Chemical compound CCCCCCCCC(=O)CC YNMZZHPSYMOGCI-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- CUNWUEBNSZSNRX-RKGWDQTMSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O CUNWUEBNSZSNRX-RKGWDQTMSA-N 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical class OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
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- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ITHKUADHDKZENI-UHFFFAOYSA-N 2-chloroethanethiol Chemical compound SCCCl ITHKUADHDKZENI-UHFFFAOYSA-N 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- QNIWMSRDAQBYHO-UHFFFAOYSA-N 2-methyldecan-4-one Chemical compound CCCCCCC(=O)CC(C)C QNIWMSRDAQBYHO-UHFFFAOYSA-N 0.000 description 1
- FWMKPJYJDJSEHR-UHFFFAOYSA-N 2-propylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CCC)=CC=C21 FWMKPJYJDJSEHR-UHFFFAOYSA-N 0.000 description 1
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- 125000003438 dodecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- HGELWZQRZUOEOJ-UHFFFAOYSA-N ethyl-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCP(O)(O)=S HGELWZQRZUOEOJ-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 229910000286 fullers earth Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229940100242 glycol stearate Drugs 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 1
- FUWGSUOSJRCEIV-UHFFFAOYSA-N phosphonothioic O,O-acid Chemical compound OP(O)=S FUWGSUOSJRCEIV-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 229940096992 potassium oleate Drugs 0.000 description 1
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical group [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000003499 redwood Nutrition 0.000 description 1
- 239000010458 rotten stone Substances 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical group [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- KWFOMJTYKROHLX-UHFFFAOYSA-M sodium;2,4,5-trichlorophenolate Chemical compound [Na+].[O-]C1=CC(Cl)=C(Cl)C=C1Cl KWFOMJTYKROHLX-UHFFFAOYSA-M 0.000 description 1
- AUPJTDWZPFFCCP-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCCN(C)CCS([O-])(=O)=O AUPJTDWZPFFCCP-GMFCBQQYSA-M 0.000 description 1
- AXKBOWBNOCUNJL-UHFFFAOYSA-M sodium;2-nitrophenolate Chemical compound [Na+].[O-]C1=CC=CC=C1[N+]([O-])=O AXKBOWBNOCUNJL-UHFFFAOYSA-M 0.000 description 1
- RTVVXRKGQRRXFJ-UHFFFAOYSA-N sodium;2-sulfobutanedioic acid Chemical class [Na].OC(=O)CC(C(O)=O)S(O)(=O)=O RTVVXRKGQRRXFJ-UHFFFAOYSA-N 0.000 description 1
- CFPLEOLETMZLIB-UHFFFAOYSA-M sodium;4-chlorophenolate Chemical compound [Na+].[O-]C1=CC=C(Cl)C=C1 CFPLEOLETMZLIB-UHFFFAOYSA-M 0.000 description 1
- KRZQYDMOEZDDGE-UHFFFAOYSA-N sodium;octan-1-olate Chemical compound [Na+].CCCCCCCC[O-] KRZQYDMOEZDDGE-UHFFFAOYSA-N 0.000 description 1
- LWLVRCRDPVJBKL-UHFFFAOYSA-M sodium;prop-2-ynoate Chemical compound [Na+].[O-]C(=O)C#C LWLVRCRDPVJBKL-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 229960005078 sorbitan sesquioleate Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Chemical class OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000002023 wood 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
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4078—Esters with 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4084—Esters with hydroxyaryl compounds
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/42—Halides thereof
Definitions
- R is alkyl of 1 to 8 carbon atoms
- R is selected from the group consisting of alkyl of 1 to 8 carbon atoms, phenyl, chlorophenyl and benzyl, R and R taken together are CH (CH CH where n is an integer from 1 to 3 inclusive;
- R is selected from the group consisting of alkyl of 1 to 8 carbon atoms and chloroalkyl having 1 to 3 carbon atoms;
- R is selected from the group consisting of alkyl of 1 to 8 carbon atoms, alkenyl of 3 to 8 carbon atoms, phenyl, alkylphenyl having 1 to 4 carbon atoms in the alkyl group, chlorophenyl, dichlorophenyl, trichlorophenyl, nitrophenyl and and
- X is halogen of atomic weight 35 to 80.
- the compounds are useful as herbicides.
- the present invention relates to oc-ChlOIOfilkYl phosphononthioates.
- Another object is to devise a novel method of preparing such compounds.
- a further object is to prepare novel herbicides.
- An additional object is to prepare herbicides having selective post emergent herbicide activity.
- R is alkyl containing 1 to 8 carbon atoms
- R is alkyl containing 1 to 8 carbon atoms
- phenyl, halophenyl or benzyl or R and R taken together is
- n is an integer from 1 to 3 inclusive
- R is alkyl containing 1 to 8 carbon atoms or hal oalkyl containing 1 to 3 carbon atoms
- the alkyl groups contain 1 to 4 carbon atoms.
- Examples of compounds within the present invention are O,S-dimethyl-u-chloroisopropylphosphonothioate, O-methyl-S-ethyl-a-chloroisopropylphosphonothioate, O,S-diethylwt-chloroisopropylphosphonothioate, 0-propargyl-S-ethyl-ot-chloroisopropylphosphonothioate, O-o-chlorophenyl-S-ethyl-a-chloroisopropylphosphonothioate, O-mchlorophenyl-S-ethyl-a-chloroisopropylphosphonothioate, O-p-chlorophenyl-S-ethyl-wchloroisopropylphosphonothioate, O-2,4-dichlorophenyl-S-ethyl-a-chloroisopropylphosphonot
- the compounds of the present invention are prepared by reacting equimolar amounts of a compound having the formula R OMe with a phosphorus containing compound having the formula A SR3
- the reaction of the present invention can be carried out with excess of alcoholate or phenolate if desired.
- the reaction is carried out at a temperature from room temperature up to 60 C.
- an appropriate solvent is also used such as an alcohol, e.g., methyl alcohol, ethyl alcohol, isopropyl alcohol, n-propyl alcohol, butyl alcohol or hexyl alcohol, dioxane or a hydrocarbon, e.g. toluene, xylene, benzene, hexane, petroleum ether, aromatic naphtha or the like.
- Examples of starting alcoholates and phenolates are sodium methylate, potassium methylate, lithium methylate, calcium ethylate, sodium ethylate, potassium ethylate, sodium octylate, sodium propylate, sodium isopropylate, potassium butylate, sodium secondary butylate, sodium phenolate, potassium phenolate, sodium O-cresylate, potassium m-cresylate, sodium p-cresyl-ate, sodium xylenylate, sodium p-chlorophenolate, sodioacetoacetic acid ester, sodium allylate, sodium propargylate, sodium salt of trimethylene chlorohydrin, sodium O-nitrophenolate, sodium-2,4,6-dichloropheno1ate, sodium 2,4,5-trichlorophenolate.
- the starting phosphorus compounds there can be used S-ethy1-ot-chloroisopropyl phosphonochloridothioate, S-methyl-a-chloroisopropyl phosphonochloridothioate,
- the starting phosphorus compounds are prepared by reacting 1) phosphorus trichloride or phosphorus tribromide With (2) a ketone having the formula and '(3) a mercaptan having the formula R SH. Equimolar quantities of the three reactants are employed.
- ketones which can be used are acetone, methyl ethyl ketone, diethyl ketone, methyl propyl ketone, methyl isopropyl ketone, ethyl butyl ketone, dipropyl ketone, methyl t-butyl ketone, isobutyl hexyl ketone, ethyl octyl ketone, acetophenone, phenyl acetone and p-chloroacetophenone, cyclopentanone, cyclohexanone and cyclobutanone.
- mercaptans which can be employed are methyl mercaptan, ethyl mercaptan, propyl mercaptan, isopropyl mercaptan, butyl mercaptan, secondary butyl mercaptan, t-butyl mercaptan, amyl mercaptan, hexyl mercaptan, octyl mercaptan, Z-ethylhexyl mercaptan, 3-chloropr0pyl mercaptan and chloroethyl mercaptan.
- EXAMPLE 2 Metallic sodium (0.07 mole) was added portionwise to 100 ml. of ethanol and the mixture was stirred until all the sodium was dissolved. To this ethanolic solution of sodium ethylate was added dropwise S-ethyl-a-chloro isopropyl-chloridophosphonothiate (0.07 mole). An exothermic reaction took place and the mixture temporarily reached 60 C. and immediate precipitation of sodium chloride occurred. The mixture was agitated for 2 hours and allowed to stand for an additional 15 hours at room temperature, until a pH of 7 was obtained.
- the compounds of the present invention can be used alone as herbicides but it has been found desirable to apply them to the plants or soil surrounding the plants, together with inert solids to form dusts or, more preferably, suspended in a suitable liquid diluent, preferably comprising water. They can be applied at widely varying rates, e.g. from 0.1-30 lbs./ acre.
- the active ingredient can be from 0.01 to 95% by weight of the entire composition when it is employed in such formulations.
- organic solvents as carriers, e.g., hydrocarbons such as benzene, toluene, xylene, kerosene, diesel oil, fuel oil, and petroleum naphtha, ketones such as acetone, methyl ethyl ketone and cyclohexanone, chlorinated hydrocarbons such as carbon tetrachloride, chloroform, trichloroethylene and perchloroethylene, esters such as ethyl acetate, amyl acetate and butyl acetate, ethers, e.g., ethylene glycol monomethyl ether and diethylene glycol monomethyl ether, alcohols, e.g., ethanol, methanol, isopropanol, amyl alcohol, ethylene glycol, propylene glycol, butyl carbitol acetate and glycerine.
- hydrocarbons such as benzene, toluene, xylene, kerosene, diesel
- novel herbicides can also be applied as aerosols, e.g., by dispersing them in air by means of a compressed gas such as dichlorodifluoromethane or trichlorofiuoromethane and other Freons, for example.
- a compressed gas such as dichlorodifluoromethane or trichlorofiuoromethane and other Freons, for example.
- the herbicides of the present invention can also be applied with adjuvants or carriers such as talc, pyrophyllite, synthetic fine silica, attapulgus clay (attaclay), kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite, fullers earth, cottonseed hulls, wheat flour, soybean flour, pumice, tripoli, wood flour, walnut shell flour, redwood flour and lignin.
- adjuvants or carriers such as talc, pyrophyllite, synthetic fine silica, attapulgus clay (attaclay), kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite, fullers earth, cottonseed hulls, wheat flour, soybean flour, pumice, tripoli, wood flour, walnut shell flour, redwood flour and lignin.
- a surface active agent in the herbicidal compositions of the present invention.
- Such surface active or wetting agents are advantageously employed in both the solid and liquid compositions.
- the surface active agent can be anionic, cationic or nonionic in character.
- Typical classes of surface active agents include alkyl sulfonate salts, alkylaryl sulfonate salts, alkyl sulfate salts, alkyl-amide sulfonate salts, alkylaryl polyether alcohols, fatty acid esters of polyhydric alcohols and the alkylene oxide addition products of such esters, and addition products of long chain mercaptans and alkylene oxides.
- Typical examples of such surface active agents include the sodium alkylbenzene sulfonates having 10 to 18 carbon atoms in the alkyl group, alkylphenol ethylene oxide condensation products, e.g., p-isooctylphenol condensed with 10 ethylene oxide units, soaps, e.g., sodium stearate and potassium oleate, sodium salt of propylnaphthalene sulfonic acid (di-Z-ethylhexyl) ester of sodium sulfosuccinic acid, sodium lauryl sulfate, sodium salt of the sulfonated monoglyceride of cocoanut fatty acids, sorbitan sesquioleate, lauryl trimethyl ammonium chloride, octadecyl trimethyl ammonium chloride, polyethylene glycol lauryl ether, polyethylene esters of fatty acids and rosin acids, e.g., Ethofat 7 and 13, sodium N-
- O,S-diethyl-a-chloroispropyl-phosphonothioate (Compound No. 3) it will be observed showed selectivity at the lbs./acre rate, affecting oats and leaving wheat relatively unharmed.
- O-phenyl-S-ethyla-chloroisopropyl phosphonothioate showed strong general herbicidal activity at 2 lbs/acre.
- R is alkyl of 1 to 8 carbon atoms
- R is selected from the group consisting of alkyl of 1 to 8 carbon atoms, phenyl, chlorophenyl and benzyl, R and R taken together are CH (CH ),,CH where n is an integer from 1 to 3 inclusive;
- R is selected from the group consisting of alkyl of 1 to 8 carbon atoms and chloroalkyl having 1 to 3 carbon atoms;
- R is selected from the group consisting of alkyl of 1 to 8 carbon atoms, alkenyl of 3 to 8 carbon atoms, phenyl, alkylphenyl having 1 to 4 carbon atoms in the alkyl group, chlorophenyl, dichlorophenyl, trichlorophenyl, nitrophenyl and (7113 -o-oHo000,H,,
- each alkyl group has 1 to 4 carbon atoms.
- each alkyl group has 1 to 4 carbon atoms.
- each alkyl group has 1 to 4 carbon atoms.
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Description
United States Patent 3,463,839 ALPHA-HALOALKYL PHOSPHONOTHIOATES Erik A. Regel, Mission, Kans., assignor to Chemagro gorporation, Kansas City, Mo., a corporation of New ork No Drawing. Original application Sept. 15, 1964, Ser. No. 396,753, new Patent No. 3,385,688, dated May 28, 1968. Divided and this application Nov. 16, 1967, Ser. No. 701,795
Int. Cl. C07f 9/40; A01n 9/36 US. Cl. 260-958 12 Claims ABSTRACT OF THE DISCLOSURE Compounds are prepared having R1 0 OR;
II/ P where R is alkyl of 1 to 8 carbon atoms, R is selected from the group consisting of alkyl of 1 to 8 carbon atoms, phenyl, chlorophenyl and benzyl, R and R taken together are CH (CH CH where n is an integer from 1 to 3 inclusive; R is selected from the group consisting of alkyl of 1 to 8 carbon atoms and chloroalkyl having 1 to 3 carbon atoms; R, is selected from the group consisting of alkyl of 1 to 8 carbon atoms, alkenyl of 3 to 8 carbon atoms, phenyl, alkylphenyl having 1 to 4 carbon atoms in the alkyl group, chlorophenyl, dichlorophenyl, trichlorophenyl, nitrophenyl and and X is halogen of atomic weight 35 to 80. The compounds are useful as herbicides.
This application is a continuation-in-part of application Ser. No. 357,761, filed Apr. 6, 1964, now Patent 3,346,669 and is a divisional application of application Ser. No. 396,753, filed Sept. 15, 1964 and now Patent 3,385,688.
The present invention relates to oc-ChlOIOfilkYl phosphononthioates.
It is an object of the present invention to prepare novel u-chloroalkyl phosphonothioates.
Another object is to devise a novel method of preparing such compounds.
A further object is to prepare novel herbicides.
An additional object is to prepare herbicides having selective post emergent herbicide activity.
Still further objects and the entire scope of applicability of the present invention will become apparent from the detailed description given hereinafter; it should be understood, however, that the detailed description and specific examples, while indicating preferred embodiments of the invention are given by way of illustration only, since various changes and modifications within the spirit and scope of the invention will become apparent to those skilled in the art from this detailed description.
It has now been found that these objects can be attained by preparing compounds having the formula where R, is alkyl containing 1 to 8 carbon atoms, R is alkyl containing 1 to 8 carbon atoms, phenyl, halophenyl or benzyl or R and R taken together is Where n is an integer from 1 to 3 inclusive; R is alkyl containing 1 to 8 carbon atoms or hal oalkyl containing 1 to 3 carbon atoms, and R is alkyl of 1 to 8 carbon atoms, alkenyl of 3 to 8 carbon atoms, alkinyl of 3 to 8 carbon atoms, phenyl, halophenyl, dihalophenyl, alkylphenyl, nitrophenyl, trihalophenyl or i C=CHO 0 0111 and X is halogen of atomic weight 35 to 80. For the best results the alkyl groups contain 1 to 4 carbon atoms.
Examples of compounds within the present invention are O,S-dimethyl-u-chloroisopropylphosphonothioate, O-methyl-S-ethyl-a-chloroisopropylphosphonothioate, O,S-diethylwt-chloroisopropylphosphonothioate, 0-propargyl-S-ethyl-ot-chloroisopropylphosphonothioate, O-o-chlorophenyl-S-ethyl-a-chloroisopropylphosphonothioate, O-mchlorophenyl-S-ethyl-a-chloroisopropylphosphonothioate, O-p-chlorophenyl-S-ethyl-wchloroisopropylphosphonothioate, O-2,4-dichlorophenyl-S-ethyl-a-chloroisopropylphosphonothiate, O-methyl-S-butyl-a-chloroisopropylphosphonothioate, O-ethyl-S-butyl-a-chlorois0pr0py1phosphonothiate, O-phenyl-S-butyl-a-chloroisopropylphosphonothioate, O-rnethyl-S-secondary butyl-a-chloroisopropylphosphonothioate, O-p-nitrophenyl-S-methyl-a-chloro-a-methyl propylphosphonothioate, O-methyl-S-ethyl-a-chloro-a-methyl propylphosphonothioate, O,S-diethyl-oc-chloro-u-tmethyl propylphosphonothioate, O-isopropenyl carboxyethyl-Sethyl-a-chloro-a-methyl propylphosphonothioate, O-2,4,S-trichlorophenyl-S-ethyl-a-chloro-a-methyl propylphosphonothioate, O-mmethylphenyl-S-ethyl-u-chloro-u-methyl propylphosphonothioate, O-phenyl-S=buty1-a-chloro-a-methyl propylphosphonothioate, O-methyl-Sethyl-oc-chloro-a-methyl isoamylphosphonothioate,
3 O,S-diethyl-a-chloro-a-ethyl propylphosphonothioate, O-methyl-S-ethyl-a-chloro-a-ethyl amylphosphonothioate, O,S-dimethyl-ot-chlorocyclopentylphosphonothioate, O,S-diethyl-u-chlorocyclopentylphosphonothioate, O-ethyl-S-propyl-a-chlorocyclopentylphosphonothioate, O,S-diethyl-u-chlorocyclohexylphosphonothioate, O-ethyl-S-butyl-a-chlorocyclohexylphosphonothioate, O,S-diethyl-a-bromoisopropylphosphonothioate, O,S-dimethyl-a-bromoisopropylphosphonothioate, O-propyl-S-butyl-a-bromo-u-methyl propylphosphonothioate, O,S-dipropyl-a-chlorocyclobutylphosphonothioate, O-octyl-S-methyl-a-chloroisopropylphosphonothioate, O-ethyl-S-octyl-u-chloroisopropylphosphonothioate, O-methyl-S-3-chloropropyl-a-chloroisopropylphosphonothioate, O-ethyl-S-chloromethyl-u-chloroisopropylphosphonothioate, O-allyl-S-methyl-a-chloroispropylphosphonothiate, 0-2-0ctenyl-S-ethyl-a-chloroisopropylphosphonothioate, 0-2-0ctinyl-S-propyl-a-chloroisopropylphosphonothioate, O-2,4-xylyl-S-methyl-u-chloroisopropylphosphonothioate, O-4butylphenyl-S-ethyl-a-chloroisopropylphosphonothioate, O,Sdimethyl-ot-chloro-a-methyl nonylphosphonothioate, O,S-dimethyl-a-octyl nonylphosphonothioate, O-methyl-S-ethyl-a-chloro-ot-benzyl ethylphosphonothioate, O,S-diethyl-a-chloro-a-phenyl ethylphosphonothioate, O-methyl-S-butyl-tx-chlor0a-p-chlor0phenyl ethylphosphonothioate, O-2,4-dichlorophenyl-S-ethyl-a-chloroisopropylphosphonothioate, and O,S-dibutylu-chloro-ot-methyl propylphosphonothioate.
The compounds of the present invention are prepared by reacting equimolar amounts of a compound having the formula R OMe with a phosphorus containing compound having the formula A SR3 The reaction of the present invention can be carried out with excess of alcoholate or phenolate if desired.
The reaction is carried out at a temperature from room temperature up to 60 C. Usually an appropriate solvent is also used such as an alcohol, e.g., methyl alcohol, ethyl alcohol, isopropyl alcohol, n-propyl alcohol, butyl alcohol or hexyl alcohol, dioxane or a hydrocarbon, e.g. toluene, xylene, benzene, hexane, petroleum ether, aromatic naphtha or the like.
Examples of starting alcoholates and phenolates are sodium methylate, potassium methylate, lithium methylate, calcium ethylate, sodium ethylate, potassium ethylate, sodium octylate, sodium propylate, sodium isopropylate, potassium butylate, sodium secondary butylate, sodium phenolate, potassium phenolate, sodium O-cresylate, potassium m-cresylate, sodium p-cresyl-ate, sodium xylenylate, sodium p-chlorophenolate, sodioacetoacetic acid ester, sodium allylate, sodium propargylate, sodium salt of trimethylene chlorohydrin, sodium O-nitrophenolate, sodium-2,4,6-dichloropheno1ate, sodium 2,4,5-trichlorophenolate.
As the starting phosphorus compounds there can be used S-ethy1-ot-chloroisopropyl phosphonochloridothioate, S-methyl-a-chloroisopropyl phosphonochloridothioate,
S-butyl-ot-chloroisopropyl phosphonochloridothioate,
S-secondary butyl-a-chloroisopropyl phosphonochloridothioate,
S-methyl-OL-ChlOI'O-Ot-H'lfithYl propylphosphonochloridothioate,
S-ethyl-a-chloro-a-methyl propylphosphonochloridothioate,
S-butyl-a-chloro-a-methyl propyl-phosphonochloridothioate,
S-ethyl-u-chloro-u-methyl-isoamylphosphonochloridothioate,
S-ethyl-a-chloro-a-ethyl propylphosphonochloridothioate,
S-ethyl-a-chloro-oc-ethyl amylphosphonochloridothionate,
S-methyl-tx-chlorocyclopentylphosphonochloridothioate,
s-ethyl-a-chlorocyclopentylphosphonochloridothioate,
s-propyl-a-chlorocyclopentylphosphonochloridothioate,
S-ethyl-a-chlorocyclohexylphosphonochloridothioate,
S-butyl-a-chlor0cyclohexylphosphonochloridothioate,
S-ethyl-a-bromoisopropylphosphonobromidothioate,
S-methyl-a-bromoisopropylphosphonobromidothioate,
S-butyl-u-bromo-u-methyl propylphosphonochloridothioate,
s-propyl-u-chlorocyclobutylphosphonochloridothioate,
S-octyl-ot-chloroisopropylphosphonochloridothioate,
S-3-chloropropyl-a-chloroisopropylphosphonochloridothioate,
S-chloromethyl-ot-chloroisopropylphosphonochloridothioate,
S-propyl-a-chloroisopropylphosphonochloridothioate,
S-methyl-a-chloro-a-methyl nonylphosphonochloridothioate,
Selhyl-OL-ChlOI'O-0t-b6I1ZY1 ethylphosphonochloridothioate,
s-ethyl-u-chloro-a phenyl ethylphosphonochloridothioate,
S-butyl-a-chloro-a-p-chlorophenylethylphosphonochloridothioate,
S-isopropyl-u-ch10roisopropylphosphonochloridothioate,
S-isobutyl-u-chloroisopropylphosphonochloridothioate,
S-methyl-a-chloro-a-methyl butylphosphonochloridothioate,
S-6thyl-0c-ChlOI'O-0L-II1lhyl hexylphosphonochloridothioate,
S-ethyl-u-chloro-u-ethyl amylphosphonochloridothioate,
S-ethyl-a-chloro-a-propyl butylphosphonochloridothioate,
S-ethyl-a-chloro-rx-methyl heptylphos-phonochloridothioate.
The starting phosphorus compounds are prepared by reacting 1) phosphorus trichloride or phosphorus tribromide With (2) a ketone having the formula and '(3) a mercaptan having the formula R SH. Equimolar quantities of the three reactants are employed.
Representative ketones Which can be used are acetone, methyl ethyl ketone, diethyl ketone, methyl propyl ketone, methyl isopropyl ketone, ethyl butyl ketone, dipropyl ketone, methyl t-butyl ketone, isobutyl hexyl ketone, ethyl octyl ketone, acetophenone, phenyl acetone and p-chloroacetophenone, cyclopentanone, cyclohexanone and cyclobutanone.
Representative mercaptans which can be employed are methyl mercaptan, ethyl mercaptan, propyl mercaptan, isopropyl mercaptan, butyl mercaptan, secondary butyl mercaptan, t-butyl mercaptan, amyl mercaptan, hexyl mercaptan, octyl mercaptan, Z-ethylhexyl mercaptan, 3-chloropr0pyl mercaptan and chloroethyl mercaptan.
EXAMPLE 1 S-ethyl-a-chloro-a-methyl propylphosphonochloridothioate Butanone (1 mole) and phosphorus trichloride (1 mole) were mixed at 0 C. and ethylmercaptan (1 mole) 1 was added dropwise while the mixture was kept below 10 C. by cooling and agitation. Hydrogen chloride was liberated and reaction mixture became yellow. After the addition of ethylmercaptan was completed the mixture was allowed to warm up to C. and agitation was 2 continued until hydrogen chloride evolution ceased. Carbontetrachloride (200 ml.) was added and the resulting solution was washed with water until the solution was almost neutral (pH 6). The carbon tetrachloride solution was dried over anhydrous sodium sulfate, filtered 25 When PBr is used in place of PC1 examples of the starting compounds formed are shown in Table 2.
Refractive R R R R B.P. index Me Me Me Br M.P Me- Et Et Br 1 5655 Me Me El: Br 100/0.005 1 5745 The compounds of the present invention are prepared as shown in Example 2.
EXAMPLE 2 Metallic sodium (0.07 mole) was added portionwise to 100 ml. of ethanol and the mixture was stirred until all the sodium was dissolved. To this ethanolic solution of sodium ethylate was added dropwise S-ethyl-a-chloro isopropyl-chloridophosphonothiate (0.07 mole). An exothermic reaction took place and the mixture temporarily reached 60 C. and immediate precipitation of sodium chloride occurred. The mixture was agitated for 2 hours and allowed to stand for an additional 15 hours at room temperature, until a pH of 7 was obtained. The mixture was then diluted with benzene and the benzene solution Washed with water, dried over anhydrous sodium sulfate, filtered and the solvent evaporated in a vacuum. The re' sulting crude O,S-diethyl a chloroisopropylphosphonothioate (0.06 mole) was obtained as a colourless oil. After purification by distillation in vacuum 0.05 mole of the pure ester was'obtained (72% yield) B.P. 70 C., n
The compounds of the present invention made by 'reacting the appropriate S-substituted-haloalkylhalothioate with the appropriate sodium alcoholate or phenolate in TAB E 1 the manner shown in Example 2 are set forth 1n Table 3.
TABLE 3 1 0 SR:
R1 0 OR; 0-1 H R ll R 2 R2 (El SR3 Compound Boiling Point Refractive o. R R- R R C./mm Hg. index 01 (48) 68/0.01 1. 5270 25 Cl -60/0.005 1. 5166 23 isoPr C1 70/0.02 1. 5055 C1 -85/0.04 1 5085 25 $001311 01 75/0.02 1 5058 ISOBu Cl 75/0.04 1 5052 Cl 75/0.15 1 5265 28 Cl /O.1 1 5095 25 Cl 1 5186 25 C1 C1 C1 C1 Me 01 --(CHz)4- C1 --(CH2)4- C1 2)r- Cl M 01 C1 C1 C1 Bu Cl C1(CH2)3 O1 Pinanyl Cl C1(CHa)s 01 Me 01 E1: 01 Me Cl El: 01 El; 01 31 Pr C1 32 lsoBu isoBu E1; 01 33 (CH2)5- E1; 01
TABLE 3.-Continued Compound Refractive N0. 1 R2 R3 R4 B.P. index Me Me 4953/0.005 1 4911 El; Me 58-62/0.008 1 5000 E1; E1; 80/0.02 1. 4825 E1; CHzC=CH 79/0.007 1. 4941" Et Ph 125/0.005 1. 5385 Et o-OlPh l30/0.005 1 5515 Et m-ClPh 135/0.01 1 5477 El; pClPh 128132/0.01 1 5477 Et 2,4-ClzPh 140/0.005 1 5574 Bu Me 7274/0.01 1 4812 Bu Et 96/0.01 1. 4861 B11 Ph l33/0.002 1. 5285 Bu p-OlPll 170/0.002 1. 5365 secBu Me 5962/0 05 1. 4897 Me p-NOzPh 180/0.07 1 5677 Et Me 81/0.06 1. 4972 Et Et 72/0.02 1 4932 El; 125130/0.04 1 5047 El; 2,4,5-Cl3Ph 168/0.3 1. 5638 Et m-CHaPh 128/0.01 1 5350 Bu Ph 150/0.005 1 5295 E1: Me 75/0.08 1. 4883 E1: Et 77/0.03 1. 4916 El; Me 10370.04 1. 4935 Me Me 83/0.08 l. 5127 26 ICHZCHZCHZ Et Et; 82/0.02 1. 4967 27 (llH CH CHa Pr Et 97/0.0l 1. 5028 28 CHQCHQCHZ Et Et 99/0.03 1. 5077 CH OHI 29 CHzCHzCH: Bu Et 130/0.01 1. 4981 CHzCHg 1 -C=CHCO1EC By substituting S-ethyl-a-brornoisopropylbromidophosphonothioate in Example 2 for the corresponding chlorido compound there was produced Qs-diethyl-a-bromoisopropylphosphonothioate, B.P. 79 C., 0.02 mm.; Refraction Index 1.5056 This is identified as compound 30 in the subsequent tables.
The compounds of the present invention can be used alone as herbicides but it has been found desirable to apply them to the plants or soil surrounding the plants, together with inert solids to form dusts or, more preferably, suspended in a suitable liquid diluent, preferably comprising water. They can be applied at widely varying rates, e.g. from 0.1-30 lbs./ acre.
There can also be added surface active agents or wetting agents and inert solids in the liquid formulations. The active ingredient can be from 0.01 to 95% by weight of the entire composition when it is employed in such formulations.
In place of water there can be employed organic solvents as carriers, e.g., hydrocarbons such as benzene, toluene, xylene, kerosene, diesel oil, fuel oil, and petroleum naphtha, ketones such as acetone, methyl ethyl ketone and cyclohexanone, chlorinated hydrocarbons such as carbon tetrachloride, chloroform, trichloroethylene and perchloroethylene, esters such as ethyl acetate, amyl acetate and butyl acetate, ethers, e.g., ethylene glycol monomethyl ether and diethylene glycol monomethyl ether, alcohols, e.g., ethanol, methanol, isopropanol, amyl alcohol, ethylene glycol, propylene glycol, butyl carbitol acetate and glycerine. Mixtures of water and organic solvents, either as solutions or emulsions, can be employed.
The novel herbicides can also be applied as aerosols, e.g., by dispersing them in air by means of a compressed gas such as dichlorodifluoromethane or trichlorofiuoromethane and other Freons, for example.
The herbicides of the present invention can also be applied with adjuvants or carriers such as talc, pyrophyllite, synthetic fine silica, attapulgus clay (attaclay), kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite, fullers earth, cottonseed hulls, wheat flour, soybean flour, pumice, tripoli, wood flour, walnut shell flour, redwood flour and lignin.
As stated it is frequently desirable to incorporate a surface active agent in the herbicidal compositions of the present invention. Such surface active or wetting agents are advantageously employed in both the solid and liquid compositions. The surface active agent can be anionic, cationic or nonionic in character.
Typical classes of surface active agents include alkyl sulfonate salts, alkylaryl sulfonate salts, alkyl sulfate salts, alkyl-amide sulfonate salts, alkylaryl polyether alcohols, fatty acid esters of polyhydric alcohols and the alkylene oxide addition products of such esters, and addition products of long chain mercaptans and alkylene oxides. Typical examples of such surface active agents include the sodium alkylbenzene sulfonates having 10 to 18 carbon atoms in the alkyl group, alkylphenol ethylene oxide condensation products, e.g., p-isooctylphenol condensed with 10 ethylene oxide units, soaps, e.g., sodium stearate and potassium oleate, sodium salt of propylnaphthalene sulfonic acid (di-Z-ethylhexyl) ester of sodium sulfosuccinic acid, sodium lauryl sulfate, sodium salt of the sulfonated monoglyceride of cocoanut fatty acids, sorbitan sesquioleate, lauryl trimethyl ammonium chloride, octadecyl trimethyl ammonium chloride, polyethylene glycol lauryl ether, polyethylene esters of fatty acids and rosin acids, e.g., Ethofat 7 and 13, sodium N-methyl-N-oleyltaurate, Turkey Red Oil, sodium dibutylnaphthalene sulfonate, sodium lignin sulfonate (Marasperse N), polyethylene glycol stearate, sodium dodecylbenzene sulfonate, tertiary dodecyl polyethylene glycol thioether (Nonionic 218), long chain ethylene oxide-propylene oxide condensation products, e.g.,
O,S-diethyl-a-chloroispropyl-phosphonothioate (Compound No. 3) it will be observed showed selectivity at the lbs./acre rate, affecting oats and leaving wheat relatively unharmed. On the other hand O-phenyl-S-ethyla-chloroisopropyl phosphonothioate showed strong general herbicidal activity at 2 lbs/acre. O-methyl-S-ethyla-chloro-a-butyl propyl-phosphonothioate and O,S-dimethyl-a-chrocyclopentylphosphonothioate both showed general herbicidal activity at 5 lbs./ acre.
I claim:
where R is alkyl of 1 to 8 carbon atoms, R is selected from the group consisting of alkyl of 1 to 8 carbon atoms, phenyl, chlorophenyl and benzyl, R and R taken together are CH (CH ),,CH where n is an integer from 1 to 3 inclusive;
R is selected from the group consisting of alkyl of 1 to 8 carbon atoms and chloroalkyl having 1 to 3 carbon atoms;
R is selected from the group consisting of alkyl of 1 to 8 carbon atoms, alkenyl of 3 to 8 carbon atoms, phenyl, alkylphenyl having 1 to 4 carbon atoms in the alkyl group, chlorophenyl, dichlorophenyl, trichlorophenyl, nitrophenyl and (7113 -o-oHo000,H,,
and X is halogen of atomic weight 35 to 80. 2. O-alkyl-S-alkyl a-chloro a-alkyl alkylphosphonothioate wherein each alkyl group has 1 to 8 carbon atoms.
3. O-alkyl-S-alkyl u-chloro-u-methyl alkylphosphonothioate wherein each alkyl group has 1 to 8 carbon atoms.
4. A compound according to claim 3 wherein each alkyl group has 1 to 4 carbon atoms.
5. O-ethyl S-ethyl 0t-ChiOI'OiSOPI'OPYIPhOSPhOIlOthiO- ate.
6. O-phenyl S-alkyl a-chloro-a-alkyl alkylphosphothioate wherein each alkyl group has 1 to 8 carbon atoms.
7. A compound according to claim 6 wherein each alkyl group has 1 to 4 carbon atoms.
8. O-phenyl-S-ethyl a-chloroisopropylphosphonothioate.
9. O-methyl S-ethyl-a-chloro a-ethyl amylphosphonothioate.
10. O-alkyl-S-alkyl u-chlorocycloalkylphosphonothioate wherein each alkyl group has 1 to -8 carbon atoms and the cycloalkyl group has 5 to 6 carbon atoms.
11. A compound according to claim 10 wherein each alkyl group has 1 to 4 carbon atoms.
12. O,S-dimethyl a-chlorocyclopentylphosphonothioate.
References Cited UNITED STATES PATENTS 2,910,402 10/ 1959 Fairchild 260-961 XR 3,094,405 6/1963 Toy et al. 260-9 (R CHARLES B. PARKER, Primary Examiner ANTON H. SUTTO, Assistant Examiner US. Cl. X.R.
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US357761A US3346669A (en) | 1964-04-06 | 1964-04-06 | Halo-phosphorus compounds and process for their preparation |
US396753A US3385688A (en) | 1964-04-06 | 1964-09-15 | Phosphonothioates as herbicides |
US70179567A | 1967-11-16 | 1967-11-16 |
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US2910402A (en) * | 1958-02-21 | 1959-10-27 | Du Pont | Compositions and methods for destroying insects |
US3094405A (en) * | 1961-02-08 | 1963-06-18 | Stauffer Chemical Co | Defoliant methods using thio esters of chloromethyl phosphonous and chloromethyl phosphonic acids |
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US3094405A (en) * | 1961-02-08 | 1963-06-18 | Stauffer Chemical Co | Defoliant methods using thio esters of chloromethyl phosphonous and chloromethyl phosphonic acids |
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