CA1133918A - Cyclic n-¬(phosphinyl and phosphinothioyl) -amino| thiomethylcarbamates - Google Patents
Cyclic n-¬(phosphinyl and phosphinothioyl) -amino| thiomethylcarbamatesInfo
- Publication number
- CA1133918A CA1133918A CA320,756A CA320756A CA1133918A CA 1133918 A CA1133918 A CA 1133918A CA 320756 A CA320756 A CA 320756A CA 1133918 A CA1133918 A CA 1133918A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- thio
- alkyl
- amino
- 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
Links
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 title claims abstract description 13
- -1 phosphinothioyl Chemical group 0.000 title claims description 77
- 125000004122 cyclic group Chemical group 0.000 title 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 32
- 241000238631 Hexapoda Species 0.000 claims abstract description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 91
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 80
- 150000001875 compounds Chemical class 0.000 claims description 72
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 67
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 67
- 125000004432 carbon atom Chemical group C* 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 241000607479 Yersinia pestis Species 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 229910052717 sulfur Chemical group 0.000 claims description 10
- 239000011593 sulfur Chemical group 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- AGQBACJHLLKTPN-UHFFFAOYSA-N CN(C(O)=O)SN[PH2]=S Chemical class CN(C(O)=O)SN[PH2]=S AGQBACJHLLKTPN-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- PZMWQNVHRKYXMS-UHFFFAOYSA-N CSC(C)=NOC(=O)NCSN(C)P1(=S)OCCCO1 Chemical compound CSC(C)=NOC(=O)NCSN(C)P1(=S)OCCCO1 PZMWQNVHRKYXMS-UHFFFAOYSA-N 0.000 claims description 2
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 claims 3
- KOCKDGSZGFZECV-UHFFFAOYSA-N CSC(C)=NOC(=O)NCSN(C(C)C)P1(=S)OCCCO1 Chemical compound CSC(C)=NOC(=O)NCSN(C(C)C)P1(=S)OCCCO1 KOCKDGSZGFZECV-UHFFFAOYSA-N 0.000 claims 2
- GZPNVOTUUNLHDH-UHFFFAOYSA-N methyl N-[[propan-2-yl-(4,4,6-trimethyl-2-sulfanylidene-1,3,2lambda5-dioxaphosphinan-2-yl)amino]sulfanylmethylcarbamoyloxy]ethanimidothioate Chemical compound CSC(C)=NOC(=O)NCSN(C(C)C)P1(=S)OC(C)CC(C)(C)O1 GZPNVOTUUNLHDH-UHFFFAOYSA-N 0.000 claims 2
- RBJUFUQERQBMOC-UHFFFAOYSA-N CSC(C)=NOC(=O)NCSN(C(C)C)P1(=S)OCCO1 Chemical compound CSC(C)=NOC(=O)NCSN(C(C)C)P1(=S)OCCO1 RBJUFUQERQBMOC-UHFFFAOYSA-N 0.000 claims 1
- YPELIRUMIKSVMG-UHFFFAOYSA-N O1CC(C)(C)COP1(=S)N(SCNC(=O)ON=C(C)SC)C1CCCCC1 Chemical compound O1CC(C)(C)COP1(=S)N(SCNC(=O)ON=C(C)SC)C1CCCCC1 YPELIRUMIKSVMG-UHFFFAOYSA-N 0.000 claims 1
- CFCWQLRRWWXPDT-UHFFFAOYSA-N O1CC(CC)(CC)COP1(=S)N(SCNC(=O)ON=C(C)SC)C1CCCCC1 Chemical compound O1CC(CC)(CC)COP1(=S)N(SCNC(=O)ON=C(C)SC)C1CCCCC1 CFCWQLRRWWXPDT-UHFFFAOYSA-N 0.000 claims 1
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 47
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 abstract description 40
- 238000009472 formulation Methods 0.000 abstract description 22
- 241000238876 Acari Species 0.000 abstract description 9
- 241000244206 Nematoda Species 0.000 abstract description 5
- 239000000376 reactant Substances 0.000 abstract description 5
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 abstract description 5
- 230000000361 pesticidal effect Effects 0.000 abstract description 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 abstract description 3
- APHZYEGZGSKAJT-UHFFFAOYSA-N aminosulfanyl N-methylcarbamate Chemical class CNC(OSN)=O APHZYEGZGSKAJT-UHFFFAOYSA-N 0.000 abstract description 2
- TXPBNIAUPLAOKZ-UHFFFAOYSA-N ClSN[PH2]=O Chemical compound ClSN[PH2]=O TXPBNIAUPLAOKZ-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 34
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 238000004458 analytical method Methods 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000003921 oil Substances 0.000 description 20
- 235000019198 oils Nutrition 0.000 description 20
- 239000004480 active ingredient Substances 0.000 description 18
- 241001521235 Spodoptera eridania Species 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 241000255993 Trichoplusia ni Species 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 239000004094 surface-active agent Substances 0.000 description 10
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 9
- 150000002923 oximes Chemical class 0.000 description 9
- 239000000575 pesticide Substances 0.000 description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- 241000254175 Anthonomus grandis Species 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 229960004132 diethyl ether Drugs 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 231100001225 mammalian toxicity Toxicity 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 241000257159 Musca domestica Species 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- MPTGKIPTVOWUDD-UHFFFAOYSA-N 2-methyl-1,3-dithiane-2-carbaldehyde Chemical compound O=CC1(C)SCCCS1 MPTGKIPTVOWUDD-UHFFFAOYSA-N 0.000 description 4
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 4
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 4
- 229940045803 cuprous chloride Drugs 0.000 description 4
- RJBIAAZJODIFHR-UHFFFAOYSA-N dihydroxy-imino-sulfanyl-$l^{5}-phosphane Chemical compound NP(O)(O)=S RJBIAAZJODIFHR-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000238818 Acheta domesticus Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 231100000674 Phytotoxicity Toxicity 0.000 description 3
- 241000485664 Protortonia cacti Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002250 absorbent Substances 0.000 description 3
- 230000002745 absorbent Effects 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000428 dust Substances 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000000885 phytotoxic effect Effects 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ZBEWVJOWXJNDGJ-UHFFFAOYSA-N 1,3-dithiolan-2-one Chemical compound O=C1SCCS1 ZBEWVJOWXJNDGJ-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- 241000256118 Aedes aegypti Species 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- 244000045232 Canavalia ensiformis Species 0.000 description 2
- 241000256244 Heliothis virescens Species 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 240000007049 Juglans regia Species 0.000 description 2
- 235000009496 Juglans regia Nutrition 0.000 description 2
- 241000238814 Orthoptera Species 0.000 description 2
- 235000010617 Phaseolus lunatus Nutrition 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
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- 239000006184 cosolvent Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
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- 244000144972 livestock Species 0.000 description 2
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- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
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- 150000003839 salts Chemical class 0.000 description 2
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- YWKHXXBSRZPNBV-UHFFFAOYSA-N (2-propan-2-yloxyphenyl) n-[(n-diethoxyphosphinothioylanilino)sulfanylmethyl]carbamate Chemical compound C=1C=CC=CC=1N(P(=S)(OCC)OCC)SCNC(=O)OC1=CC=CC=C1OC(C)C YWKHXXBSRZPNBV-UHFFFAOYSA-N 0.000 description 1
- JNYAEWCLZODPBN-KVTDHHQDSA-N (2r,3r,4r)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@@H](O)[C@H]1O JNYAEWCLZODPBN-KVTDHHQDSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- LRBDQLCVYKZZHD-UHFFFAOYSA-N 2-ethyl-1,3-dithiane-2-carbaldehyde Chemical compound CCC1(C=O)SCCCS1 LRBDQLCVYKZZHD-UHFFFAOYSA-N 0.000 description 1
- CNXDLZCBSCSSJC-UHFFFAOYSA-N 2-methyl-1,3-dithiolane-2-carbaldehyde Chemical compound O=CC1(C)SCCS1 CNXDLZCBSCSSJC-UHFFFAOYSA-N 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
- MQFPSSOEXVDRHY-UHFFFAOYSA-N 5,5-dimethyl-n-propan-2-yl-2-sulfanylidene-1,3,2$l^{5}-dioxaphosphinan-2-amine Chemical compound CC(C)NP1(=S)OCC(C)(C)CO1 MQFPSSOEXVDRHY-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
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- 240000002470 Amphicarpaea bracteata Species 0.000 description 1
- 235000000073 Amphicarpaea bracteata Nutrition 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000238658 Blattella Species 0.000 description 1
- LLZMSPKJNHNGNS-UHFFFAOYSA-N C(C)P(=S)(CC)CNSCNC(OC1=CC=CC=2CC(OC21)(C)C)=O Chemical compound C(C)P(=S)(CC)CNSCNC(OC1=CC=CC=2CC(OC21)(C)C)=O LLZMSPKJNHNGNS-UHFFFAOYSA-N 0.000 description 1
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- KLOYISNMNAGUFP-UHFFFAOYSA-N CCC1(CC)COP(=S)OC1 Chemical compound CCC1(CC)COP(=S)OC1 KLOYISNMNAGUFP-UHFFFAOYSA-N 0.000 description 1
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- 150000001298 alcohols Chemical class 0.000 description 1
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- 239000012736 aqueous medium Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- AISZOMRXKKCPIS-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioylsulfanylacetate Chemical compound CCOC(=O)CSP(=S)(OCC)OCC AISZOMRXKKCPIS-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
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- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
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- 239000002917 insecticide Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- GYKXQTKSWLAUIT-UHFFFAOYSA-N m-cumenyl methylcarbamate Chemical group CNC(=O)OC1=CC=CC(C(C)C)=C1 GYKXQTKSWLAUIT-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- PUZQFWKUYSHJQQ-UHFFFAOYSA-N methyl n-[[(5,5-dimethyl-2-sulfanylidene-1,3,2$l^{5}-dioxaphosphinan-2-yl)-propan-2-ylamino]sulfanylmethylcarbamoyloxy]ethanimidothioate Chemical compound CSC(C)=NOC(=O)NCSN(C(C)C)P1(=S)OCC(C)(C)CO1 PUZQFWKUYSHJQQ-UHFFFAOYSA-N 0.000 description 1
- FJAJUICHLVUILZ-UHFFFAOYSA-N methyl n-[[diethoxyphosphinothioyl(propan-2-yl)amino]sulfanylmethylcarbamoyloxy]ethanimidothioate Chemical compound CCOP(=S)(OCC)N(C(C)C)SCNC(=O)ON=C(C)SC FJAJUICHLVUILZ-UHFFFAOYSA-N 0.000 description 1
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical class CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 1
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- 230000003129 miticidal effect Effects 0.000 description 1
- 125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VSVLZHLRBOPTRA-UHFFFAOYSA-N n-cyclohexyl-5,5-dimethyl-2-sulfanylidene-1,3,2$l^{5}-dioxaphosphinan-2-amine Chemical compound O1CC(C)(C)COP1(=S)NC1CCCCC1 VSVLZHLRBOPTRA-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—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)
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus as a ring member
-
- 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
- C07F9/657154—Cyclic esteramides of oxyacids of phosphorus
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87495978A | 1978-02-03 | 1978-02-03 | |
| US874,959 | 1978-02-03 | ||
| US05/962,266 US4208409A (en) | 1977-02-04 | 1978-11-20 | N-[(phosphinyl or phosphinothioyl)amino]thio-methylcarbamates and pesticidal methods |
| US962,266 | 1978-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1133918A true CA1133918A (en) | 1982-10-19 |
Family
ID=27128362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA320,756A Expired CA1133918A (en) | 1978-02-03 | 1979-02-02 | Cyclic n-¬(phosphinyl and phosphinothioyl) -amino| thiomethylcarbamates |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS5828879B2 (it) |
| AU (1) | AU521661B2 (it) |
| BR (1) | BR7900672A (it) |
| CA (1) | CA1133918A (it) |
| CH (1) | CH638815A5 (it) |
| DD (1) | DD141779A5 (it) |
| DE (1) | DE2902647A1 (it) |
| DK (1) | DK45379A (it) |
| EG (1) | EG14058A (it) |
| ES (1) | ES477417A1 (it) |
| FR (1) | FR2422673B1 (it) |
| GB (1) | GB2015527B (it) |
| HU (1) | HU184209B (it) |
| IL (1) | IL56502A (it) |
| IT (1) | IT1202876B (it) |
| NL (1) | NL7900857A (it) |
| OA (1) | OA06176A (it) |
| PL (1) | PL115203B1 (it) |
| YU (1) | YU24179A (it) |
-
1979
- 1979-01-24 DE DE19792902647 patent/DE2902647A1/de not_active Withdrawn
- 1979-01-24 AU AU43607/79A patent/AU521661B2/en not_active Ceased
- 1979-01-25 IL IL56502A patent/IL56502A/xx unknown
- 1979-02-02 BR BR7900672A patent/BR7900672A/pt unknown
- 1979-02-02 CA CA320,756A patent/CA1133918A/en not_active Expired
- 1979-02-02 NL NL7900857A patent/NL7900857A/xx not_active Application Discontinuation
- 1979-02-02 HU HU79UO153A patent/HU184209B/hu unknown
- 1979-02-02 ES ES477417A patent/ES477417A1/es not_active Expired
- 1979-02-02 GB GB7903755A patent/GB2015527B/en not_active Expired
- 1979-02-02 FR FR7902723A patent/FR2422673B1/fr not_active Expired
- 1979-02-02 DK DK45379A patent/DK45379A/da not_active Application Discontinuation
- 1979-02-02 CH CH106979A patent/CH638815A5/de not_active IP Right Cessation
- 1979-02-02 IT IT19865/79A patent/IT1202876B/it active
- 1979-02-02 DD DD79210794A patent/DD141779A5/de unknown
- 1979-02-02 JP JP54011322A patent/JPS5828879B2/ja not_active Expired
- 1979-02-02 YU YU00241/79A patent/YU24179A/xx unknown
- 1979-02-03 PL PL1979213213A patent/PL115203B1/pl unknown
- 1979-02-03 EG EG69/79A patent/EG14058A/xx active
- 1979-02-03 OA OA56726A patent/OA06176A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7900857A (nl) | 1979-08-07 |
| FR2422673A1 (fr) | 1979-11-09 |
| GB2015527B (en) | 1982-04-21 |
| DE2902647A1 (de) | 1979-08-09 |
| AU521661B2 (en) | 1982-04-22 |
| DD141779A5 (de) | 1980-05-21 |
| PL115203B1 (en) | 1981-03-31 |
| DK45379A (da) | 1979-08-04 |
| BR7900672A (pt) | 1979-09-04 |
| GB2015527A (en) | 1979-09-12 |
| JPS54115377A (en) | 1979-09-07 |
| YU24179A (en) | 1983-02-28 |
| IT1202876B (it) | 1989-02-15 |
| JPS5828879B2 (ja) | 1983-06-18 |
| HU184209B (en) | 1984-07-30 |
| IL56502A (en) | 1983-11-30 |
| FR2422673B1 (fr) | 1985-06-28 |
| EG14058A (en) | 1984-06-30 |
| IT7919865A0 (it) | 1979-02-02 |
| AU4360779A (en) | 1979-08-09 |
| PL213213A1 (it) | 1980-02-25 |
| OA06176A (fr) | 1981-06-30 |
| ES477417A1 (es) | 1980-07-01 |
| CH638815A5 (de) | 1983-10-14 |
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