CA1086644A - Phosphorus-containing fungicides - Google Patents
Phosphorus-containing fungicidesInfo
- Publication number
- CA1086644A CA1086644A CA247,826A CA247826A CA1086644A CA 1086644 A CA1086644 A CA 1086644A CA 247826 A CA247826 A CA 247826A CA 1086644 A CA1086644 A CA 1086644A
- Authority
- CA
- Canada
- Prior art keywords
- thiophosphite
- radical
- fungicidal composition
- composition according
- 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
- 239000000417 fungicide Substances 0.000 title claims abstract description 5
- 229910052698 phosphorus Inorganic materials 0.000 title claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims description 3
- 239000011574 phosphorus Substances 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- -1 alkenyloxyalkyl radical Chemical class 0.000 claims abstract description 46
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 150000001768 cations Chemical class 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 39
- 230000000855 fungicidal effect Effects 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 241000233866 Fungi Species 0.000 claims description 11
- 239000004480 active ingredient Substances 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 239000011734 sodium Substances 0.000 claims description 11
- 239000011575 calcium Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
- 239000011149 active material Substances 0.000 claims description 8
- 229910052791 calcium Inorganic materials 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 8
- 239000011777 magnesium Chemical group 0.000 claims description 7
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical compound [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- 208000031888 Mycoses Diseases 0.000 claims description 5
- 239000012141 concentrate Substances 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 239000004563 wettable powder Substances 0.000 claims description 5
- 241000235349 Ascomycota Species 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- KPQGFNDKTRFTLX-UHFFFAOYSA-N barium(2+) dioxido(sulfido)phosphane Chemical compound P([S-])([O-])[O-].[Ba+2].P([S-])([O-])[O-].[Ba+2].[Ba+2] KPQGFNDKTRFTLX-UHFFFAOYSA-N 0.000 claims description 4
- KHGQAGLWQRCYAT-UHFFFAOYSA-N disodium ethylsulfanyl(dioxido)phosphane Chemical compound P(SCC)([O-])[O-].[Na+].[Na+] KHGQAGLWQRCYAT-UHFFFAOYSA-N 0.000 claims description 4
- 239000000945 filler Substances 0.000 claims description 4
- 229910001385 heavy metal Inorganic materials 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 241000221198 Basidiomycota Species 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 3
- 230000001070 adhesive effect Effects 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- UONFDRFWKRFEDU-UHFFFAOYSA-N 2-hydroxy-1,3,2-dioxaphosphinane Chemical class OP1OCCCO1 UONFDRFWKRFEDU-UHFFFAOYSA-N 0.000 claims description 2
- GRZZTYUZNNKOFW-UHFFFAOYSA-N 2-hydroxy-1,3,2-dioxaphospholane Chemical class OP1OCCO1 GRZZTYUZNNKOFW-UHFFFAOYSA-N 0.000 claims description 2
- SJDGTRIOQBZYSU-UHFFFAOYSA-N NP(O)(O)O Chemical class NP(O)(O)O SJDGTRIOQBZYSU-UHFFFAOYSA-N 0.000 claims description 2
- XGTBHLSBVIDRQX-UHFFFAOYSA-N P(SC(CO)C)([O-])[O-].[Ca+2] Chemical compound P(SC(CO)C)([O-])[O-].[Ca+2] XGTBHLSBVIDRQX-UHFFFAOYSA-N 0.000 claims description 2
- DCRVFPUBNKJBDQ-UHFFFAOYSA-N P(SCC)([O-])[O-].[Ba+2] Chemical compound P(SCC)([O-])[O-].[Ba+2] DCRVFPUBNKJBDQ-UHFFFAOYSA-N 0.000 claims description 2
- HFAXJARKRJNZBV-UHFFFAOYSA-N P(SCC)([O-])[O-].[Ca+2] Chemical compound P(SCC)([O-])[O-].[Ca+2] HFAXJARKRJNZBV-UHFFFAOYSA-N 0.000 claims description 2
- RFYBNOZYOOWYBK-UHFFFAOYSA-N P(SCCCO)([O-])[O-].[Mg+2] Chemical compound P(SCCCO)([O-])[O-].[Mg+2] RFYBNOZYOOWYBK-UHFFFAOYSA-N 0.000 claims description 2
- MLQDHGSEUBWFOB-UHFFFAOYSA-N P([S-])([O-])[O-].[Ca+2].P([S-])([O-])[O-].[Ca+2].[Ca+2] Chemical compound P([S-])([O-])[O-].[Ca+2].P([S-])([O-])[O-].[Ca+2].[Ca+2] MLQDHGSEUBWFOB-UHFFFAOYSA-N 0.000 claims description 2
- 230000000895 acaricidal effect Effects 0.000 claims description 2
- 239000000642 acaricide Substances 0.000 claims description 2
- 239000000443 aerosol Substances 0.000 claims description 2
- 229910052788 barium Chemical group 0.000 claims description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical group [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 2
- OISOEVXHXBNOKU-UHFFFAOYSA-N calcium dioxido(propan-2-ylsulfanyl)phosphane Chemical compound P(SC(C)C)([O-])[O-].[Ca+2] OISOEVXHXBNOKU-UHFFFAOYSA-N 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 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 2
- 150000005690 diesters Chemical class 0.000 claims description 2
- 238000010790 dilution Methods 0.000 claims description 2
- 239000012895 dilution Substances 0.000 claims description 2
- WSICUDWROFOGMI-UHFFFAOYSA-N disodium 3-dioxidophosphanylsulfanyl-2,2-dimethylpropan-1-ol Chemical compound P(SCC(CO)(C)C)([O-])[O-].[Na+].[Na+] WSICUDWROFOGMI-UHFFFAOYSA-N 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 150000003949 imides Chemical class 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 230000000149 penetrating effect Effects 0.000 claims description 2
- VXTFGYMINLXJPW-UHFFFAOYSA-N phosphinane Chemical class C1CCPCC1 VXTFGYMINLXJPW-UHFFFAOYSA-N 0.000 claims description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims 3
- 206010061217 Infestation Diseases 0.000 claims 2
- 239000002270 dispersing agent Substances 0.000 claims 2
- 230000002538 fungal effect Effects 0.000 claims 2
- 239000004552 water soluble powder Substances 0.000 claims 2
- KACIRHQYMPINJM-UHFFFAOYSA-N CC(C(C)SP(O)O)O.N.N Chemical compound CC(C(C)SP(O)O)O.N.N KACIRHQYMPINJM-UHFFFAOYSA-N 0.000 claims 1
- MKBVMLHYBFOOQV-UHFFFAOYSA-N CC(C)(CO)CSP(O)O.C1=CC=NC=C1.C1=CC=NC=C1 Chemical compound CC(C)(CO)CSP(O)O.C1=CC=NC=C1.C1=CC=NC=C1 MKBVMLHYBFOOQV-UHFFFAOYSA-N 0.000 claims 1
- YYQVPMPRLHJUMI-UHFFFAOYSA-N CC(C)(CO)CSP(O)O.N.N Chemical compound CC(C)(CO)CSP(O)O.N.N YYQVPMPRLHJUMI-UHFFFAOYSA-N 0.000 claims 1
- XHZZMQMDKTYUOA-UHFFFAOYSA-N CC(CO)SP(O)O.N.N Chemical compound CC(CO)SP(O)O.N.N XHZZMQMDKTYUOA-UHFFFAOYSA-N 0.000 claims 1
- GVYPARLOFIXWFR-UHFFFAOYSA-N CC(CSP(O)O)O.N.N Chemical compound CC(CSP(O)O)O.N.N GVYPARLOFIXWFR-UHFFFAOYSA-N 0.000 claims 1
- NXNACSKSQUUAND-UHFFFAOYSA-N CCNCC.CCNCC.CC(C)(CO)CSP(O)O Chemical compound CCNCC.CCNCC.CC(C)(CO)CSP(O)O NXNACSKSQUUAND-UHFFFAOYSA-N 0.000 claims 1
- KJCZRQYWTCTIJX-UHFFFAOYSA-N CCNCC.CCNCC.CC(C)SP(O)O Chemical compound CCNCC.CCNCC.CC(C)SP(O)O KJCZRQYWTCTIJX-UHFFFAOYSA-N 0.000 claims 1
- PGYLMBMZZMBSPQ-UHFFFAOYSA-N CCNCC.CCNCC.CC(CO)SP(O)O Chemical compound CCNCC.CCNCC.CC(CO)SP(O)O PGYLMBMZZMBSPQ-UHFFFAOYSA-N 0.000 claims 1
- QGEWOKPEVDYTAQ-UHFFFAOYSA-N CCNCC.CCNCC.CC(CSP(O)O)O Chemical compound CCNCC.CCNCC.CC(CSP(O)O)O QGEWOKPEVDYTAQ-UHFFFAOYSA-N 0.000 claims 1
- DEAFWBBUYXCWIJ-UHFFFAOYSA-N CCNCC.CCNCC.CCSP(O)O Chemical compound CCNCC.CCNCC.CCSP(O)O DEAFWBBUYXCWIJ-UHFFFAOYSA-N 0.000 claims 1
- ZPQIHURIBNOPLI-UHFFFAOYSA-N CCNCC.CCNCC.OCCCSP(O)O Chemical compound CCNCC.CCNCC.OCCCSP(O)O ZPQIHURIBNOPLI-UHFFFAOYSA-N 0.000 claims 1
- ZWJUENLCKCRQEB-UHFFFAOYSA-N CCSP(O)O.N.N Chemical compound CCSP(O)O.N.N ZWJUENLCKCRQEB-UHFFFAOYSA-N 0.000 claims 1
- 239000001692 EU approved anti-caking agent Substances 0.000 claims 1
- CXXABORPPMKKTP-UHFFFAOYSA-N OCCCSP(O)O.N.N Chemical compound OCCCSP(O)O.N.N CXXABORPPMKKTP-UHFFFAOYSA-N 0.000 claims 1
- RXQBXEIMYYZLFD-UHFFFAOYSA-N OCCSP(O)O.N.N Chemical compound OCCSP(O)O.N.N RXQBXEIMYYZLFD-UHFFFAOYSA-N 0.000 claims 1
- RJRLAKNZAIETSG-UHFFFAOYSA-N P(SC(C(O)C)C)([O-])[O-].[Ca+2] Chemical compound P(SC(C(O)C)C)([O-])[O-].[Ca+2] RJRLAKNZAIETSG-UHFFFAOYSA-N 0.000 claims 1
- MRHMVGNWXGSAOH-UHFFFAOYSA-N P(SCC(CO)(C)C)([O-])[O-].[Ca+2] Chemical compound P(SCC(CO)(C)C)([O-])[O-].[Ca+2] MRHMVGNWXGSAOH-UHFFFAOYSA-N 0.000 claims 1
- BGPMZXKAKPFLQS-UHFFFAOYSA-N P(SCC(CO)(C)C)([O-])[O-].[Mg+2] Chemical compound P(SCC(CO)(C)C)([O-])[O-].[Mg+2] BGPMZXKAKPFLQS-UHFFFAOYSA-N 0.000 claims 1
- WVVSZYFIVZMLLX-UHFFFAOYSA-N P(SCC(O)C)([O-])[O-].[Na+].[Na+] Chemical compound P(SCC(O)C)([O-])[O-].[Na+].[Na+] WVVSZYFIVZMLLX-UHFFFAOYSA-N 0.000 claims 1
- DIZHXRWYGQRFJZ-UHFFFAOYSA-N P(SCC)([O-])[O-].[Mg+2] Chemical compound P(SCC)([O-])[O-].[Mg+2] DIZHXRWYGQRFJZ-UHFFFAOYSA-N 0.000 claims 1
- FUXOPEHQZYWEIV-UHFFFAOYSA-N P(SCCC)([O-])[O-].[Ca+2] Chemical compound P(SCCC)([O-])[O-].[Ca+2] FUXOPEHQZYWEIV-UHFFFAOYSA-N 0.000 claims 1
- QGJPKZYMNIUBFB-UHFFFAOYSA-N P(SCCCO)([O-])[O-].[Ca+2] Chemical compound P(SCCCO)([O-])[O-].[Ca+2] QGJPKZYMNIUBFB-UHFFFAOYSA-N 0.000 claims 1
- QAXPMOJNVAEYIL-UHFFFAOYSA-N P([S-])([O-])[O-].[Na+].[Na+].[Na+] Chemical compound P([S-])([O-])[O-].[Na+].[Na+].[Na+] QAXPMOJNVAEYIL-UHFFFAOYSA-N 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- QXZILXDSULYPQH-UHFFFAOYSA-N calcium 1-dioxidophosphanylsulfanylpropan-2-ol Chemical compound P(SCC(C)O)([O-])[O-].[Ca+2] QXZILXDSULYPQH-UHFFFAOYSA-N 0.000 claims 1
- PFPGYRCCFPKXEL-UHFFFAOYSA-N disodium 2-dioxidophosphanylsulfanylpropan-1-ol Chemical compound P(SC(CO)C)([O-])[O-].[Na+].[Na+] PFPGYRCCFPKXEL-UHFFFAOYSA-N 0.000 claims 1
- UYDYBRSVOLEGMP-UHFFFAOYSA-N disodium dioxido(propan-2-ylsulfanyl)phosphane Chemical compound P(SC(C)C)([O-])[O-].[Na+].[Na+] UYDYBRSVOLEGMP-UHFFFAOYSA-N 0.000 claims 1
- 238000010410 dusting Methods 0.000 claims 1
- 239000004495 emulsifiable concentrate Substances 0.000 claims 1
- 239000003995 emulsifying agent Substances 0.000 claims 1
- 239000002917 insecticide Substances 0.000 claims 1
- ZVWAPUQPUYOZEK-UHFFFAOYSA-N magnesium 3-dioxidophosphanylsulfanylbutan-2-ol Chemical compound P(SC(C(O)C)C)([O-])[O-].[Mg+2] ZVWAPUQPUYOZEK-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 239000004546 suspension concentrate Substances 0.000 claims 1
- 238000009736 wetting Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- TYQTYRXEMJXFJG-UHFFFAOYSA-N phosphorothious acid Chemical compound OP(O)S TYQTYRXEMJXFJG-UHFFFAOYSA-N 0.000 abstract description 3
- 125000000232 haloalkynyl group Chemical group 0.000 abstract description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000004971 nitroalkyl group Chemical group 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 33
- 150000002500 ions Chemical class 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 244000046052 Phaseolus vulgaris Species 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 241000233614 Phytophthora Species 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000036961 partial effect Effects 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
- 244000099147 Ananas comosus Species 0.000 description 3
- 240000004160 Capsicum annuum Species 0.000 description 3
- 241000518994 Conta Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009109 curative therapy Methods 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-O diethylammonium Chemical compound CC[NH2+]CC HPNMFZURTQLUMO-UHFFFAOYSA-O 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000003449 preventive effect Effects 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 235000007119 Ananas comosus Nutrition 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 240000009088 Fragaria x ananassa Species 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 241001483078 Phyto Species 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000010902 straw Substances 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- LABRPRANVKSMGP-UHFFFAOYSA-N 1,3,2-dioxaphosphinane Chemical class C1COPOC1 LABRPRANVKSMGP-UHFFFAOYSA-N 0.000 description 1
- QFMDFTQOJHFVNR-UHFFFAOYSA-N 1-[2,2-dichloro-1-(4-ethylphenyl)ethyl]-4-ethylbenzene Chemical compound C1=CC(CC)=CC=C1C(C(Cl)Cl)C1=CC=C(CC)C=C1 QFMDFTQOJHFVNR-UHFFFAOYSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- YVSBRIIXGWWSEV-UHFFFAOYSA-N 3-hydroxypropylsulfanylphosphonous acid Chemical class C(CO)CSP(O)O YVSBRIIXGWWSEV-UHFFFAOYSA-N 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000233685 Bremia lactucae Species 0.000 description 1
- BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 241000222199 Colletotrichum Species 0.000 description 1
- 244000241257 Cucumis melo Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- 101100478173 Drosophila melanogaster spen gene Proteins 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 240000001812 Hyssopus officinalis Species 0.000 description 1
- 235000010650 Hyssopus officinalis Nutrition 0.000 description 1
- 101100384355 Mus musculus Ctnnbip1 gene Proteins 0.000 description 1
- 101100513476 Mus musculus Spen gene Proteins 0.000 description 1
- 229910003873 O—P—O Inorganic materials 0.000 description 1
- 241000169463 Peronospora sp. Species 0.000 description 1
- 244000025272 Persea americana Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 241000233637 Phytophthora palmivora Species 0.000 description 1
- 241000626605 Phytophthora phaseoli Species 0.000 description 1
- 241000031556 Phytophthora sp. Species 0.000 description 1
- 241001281803 Plasmopara viticola Species 0.000 description 1
- 241001501939 Prionailurus iriomotensis Species 0.000 description 1
- 241000342307 Pseudoperonospora humuli Species 0.000 description 1
- 241000022563 Rema Species 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 1
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005452 alkenyloxyalkyl group Chemical group 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 159000000009 barium salts Chemical class 0.000 description 1
- 235000001046 cacaotero Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229920003211 cis-1,4-polyisoprene Polymers 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-O ethylaminium Chemical compound CC[NH3+] QUSNBJAOOMFDIB-UHFFFAOYSA-O 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 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
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
- 229920000940 maneb Polymers 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 229940099990 ogen Drugs 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- HNSYHCVBZGSRGQ-UHFFFAOYSA-N tripotassium dioxido(sulfido)phosphane Chemical class P([S-])([O-])[O-].[K+].[K+].[K+] HNSYHCVBZGSRGQ-UHFFFAOYSA-N 0.000 description 1
- 230000001018 virulence Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- 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
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
-
- 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
- C07F9/201—Esters of thiophosphorus acids
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7508642A FR2303476A1 (fr) | 1975-03-14 | 1975-03-14 | Composition fongicide a base de thiophosphites |
| FR7508642 | 1975-03-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1086644A true CA1086644A (en) | 1980-09-30 |
Family
ID=9152798
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA247,826A Expired CA1086644A (en) | 1975-03-14 | 1976-03-12 | Phosphorus-containing fungicides |
Country Status (25)
| Country | Link |
|---|---|
| JP (3) | JPS51128435A (it) |
| AR (1) | AR228418A1 (it) |
| AU (1) | AU507474B2 (it) |
| BE (1) | BE839514A (it) |
| BG (2) | BG24944A3 (it) |
| BR (1) | BR7601525A (it) |
| CA (1) | CA1086644A (it) |
| CH (1) | CH610185A5 (it) |
| CS (2) | CS193082B2 (it) |
| DD (1) | DD125771A5 (it) |
| DE (1) | DE2606761C2 (it) |
| ES (1) | ES446025A1 (it) |
| FR (1) | FR2303476A1 (it) |
| GB (1) | GB1525339A (it) |
| GR (1) | GR60033B (it) |
| HU (1) | HU177025B (it) |
| IL (1) | IL49203A (it) |
| IT (1) | IT1058002B (it) |
| NL (1) | NL183889C (it) |
| OA (1) | OA05271A (it) |
| PH (1) | PH14304A (it) |
| PL (2) | PL99758B1 (it) |
| PT (1) | PT64902B (it) |
| SU (1) | SU651649A3 (it) |
| ZA (1) | ZA761522B (it) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6021553B2 (ja) * | 1979-09-14 | 1985-05-28 | 三菱マテリアル株式会社 | 白色導電性被覆粉末およびその製造法 |
-
1975
- 1975-03-14 FR FR7508642A patent/FR2303476A1/fr active Granted
-
1976
- 1976-02-19 DE DE2606761A patent/DE2606761C2/de not_active Expired
- 1976-03-05 NL NLAANVRAGE7602309,A patent/NL183889C/xx not_active IP Right Cessation
- 1976-03-11 CS CS77458A patent/CS193082B2/cs unknown
- 1976-03-11 CS CS761595A patent/CS193066B2/cs unknown
- 1976-03-12 SU SU762333104A patent/SU651649A3/ru active
- 1976-03-12 BG BG033550A patent/BG24944A3/xx not_active Expired
- 1976-03-12 PH PH18206A patent/PH14304A/en unknown
- 1976-03-12 DD DD191815A patent/DD125771A5/xx unknown
- 1976-03-12 BR BR7601525A patent/BR7601525A/pt unknown
- 1976-03-12 PT PT64902A patent/PT64902B/pt unknown
- 1976-03-12 AU AU11919/76A patent/AU507474B2/en not_active Expired
- 1976-03-12 CH CH312476A patent/CH610185A5/xx not_active IP Right Cessation
- 1976-03-12 BG BG032598A patent/BG24938A3/xx unknown
- 1976-03-12 ZA ZA761522A patent/ZA761522B/xx unknown
- 1976-03-12 CA CA247,826A patent/CA1086644A/en not_active Expired
- 1976-03-12 IL IL49203A patent/IL49203A/xx unknown
- 1976-03-12 BE BE165119A patent/BE839514A/xx not_active IP Right Cessation
- 1976-03-12 AR AR262536A patent/AR228418A1/es active
- 1976-03-12 ES ES446025A patent/ES446025A1/es not_active Expired
- 1976-03-12 HU HU76PI509A patent/HU177025B/hu unknown
- 1976-03-12 GB GB9986/76A patent/GB1525339A/en not_active Expired
- 1976-03-13 OA OA55765A patent/OA05271A/xx unknown
- 1976-03-13 PL PL1976187915A patent/PL99758B1/pl unknown
- 1976-03-13 JP JP51027599A patent/JPS51128435A/ja active Granted
- 1976-03-13 GR GR50298A patent/GR60033B/el unknown
- 1976-03-13 PL PL1976200283A patent/PL101317B1/pl unknown
- 1976-03-15 IT IT48579/76A patent/IT1058002B/it active
-
1984
- 1984-07-05 JP JP59140407A patent/JPS6069086A/ja active Granted
-
1985
- 1985-05-28 JP JP11517985A patent/JPS6133191A/ja active Granted
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |