ZA200602091B - Use of alcohol-oxyalkylates in the form of adjuvants for benzamidoxime fungicidal derivatives, appropriate agents and kits - Google Patents

Info

Publication number

ZA200602091B

ZA200602091B ZA200602091A ZA200602091A ZA200602091B ZA 200602091 B ZA200602091 B ZA 200602091B ZA 200602091 A ZA200602091 A ZA 200602091A ZA 200602091 A ZA200602091 A ZA 200602091A ZA 200602091 B ZA200602091 B ZA 200602091B

Authority

ZA

South Africa

Prior art keywords

composition according

alcohol

alkyl

weight

wherei

Prior art date

2003-08-14

Links

• Espacenet
• Global Dossier
• Discuss

• MXOQNVMDKHLYCZ-UHFFFAOYSA-N benzamidoxime Chemical compound ON=C(N)C1=CC=CC=C1 MXOQNVMDKHLYCZ-UHFFFAOYSA-N 0.000 title claims description 32
• 230000000855 fungicidal effect Effects 0.000 title claims description 13
• 239000002671 adjuvant Substances 0.000 title description 14
• 239000003795 chemical substances by application Substances 0.000 title description 5
• 239000000203 mixture Substances 0.000 claims description 134
• 235000019441 ethanol Nutrition 0.000 claims description 110
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 87
• 150000001875 compounds Chemical class 0.000 claims description 40
• 239000004435 Oxo alcohol Substances 0.000 claims description 19
• 125000004432 carbon atom Chemical group C* 0.000 claims description 17
• 239000001257 hydrogen Substances 0.000 claims description 16
• 229910052739 hydrogen Inorganic materials 0.000 claims description 16
• 150000002923 oximes Chemical class 0.000 claims description 15
• 229910052736 halogen Inorganic materials 0.000 claims description 14
• 150000002367 halogens Chemical class 0.000 claims description 14
• 238000005984 hydrogenation reaction Methods 0.000 claims description 14
• VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 11
• IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 11
• JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 claims description 11
• 239000005810 Metrafenone Substances 0.000 claims description 10
• AMSPWOYQQAWRRM-UHFFFAOYSA-N metrafenone Chemical compound COC1=CC=C(Br)C(C)=C1C(=O)C1=C(C)C=C(OC)C(OC)=C1OC AMSPWOYQQAWRRM-UHFFFAOYSA-N 0.000 claims description 10
• ZMYFCFLJBGAQRS-IRXDYDNUSA-N (2R,3S)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@@]1(CN2N=CN=C2)[C@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IRXDYDNUSA-N 0.000 claims description 8
• 239000005767 Epoxiconazole Substances 0.000 claims description 8
• 125000001424 substituent group Chemical group 0.000 claims description 7
• 239000005869 Pyraclostrobin Substances 0.000 claims description 6
• 239000011737 fluorine Substances 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 claims description 6
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 5
• 229960004756 ethanol Drugs 0.000 claims description 5
• QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
• VEPOHXYIFQMVHW-PVJVQHJQSA-N (2r,3r)-2,3-dihydroxybutanedioic acid;(2s,3s)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.O1CCN(C)[C@@H](C)[C@@H]1C1=CC=CC=C1 VEPOHXYIFQMVHW-PVJVQHJQSA-N 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• ZMYFCFLJBGAQRS-IAGOWNOFSA-N (2S,3R)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@]1(CN2N=CN=C2)[C@@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IAGOWNOFSA-N 0.000 claims description 2
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
• 239000000539 dimer Substances 0.000 claims description 2
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
• YLQLIQIAXYRMDL-UHFFFAOYSA-N propylheptyl alcohol Chemical compound CCCCCC(CO)CCC YLQLIQIAXYRMDL-UHFFFAOYSA-N 0.000 claims description 2
• 125000001544 thienyl group Chemical group 0.000 claims description 2
• VMXUWOKSQNHOCA-UKTHLTGXSA-N ranitidine Chemical compound [O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-UKTHLTGXSA-N 0.000 claims 2
• LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims 1
• NNLXOLJQTHDVIO-UHFFFAOYSA-N 6-(difluoromethoxy)-2,3-difluoro-n-(2-phenylacetyl)benzamide Chemical compound FC(F)OC1=CC=C(F)C(F)=C1C(=O)NC(=O)CC1=CC=CC=C1 NNLXOLJQTHDVIO-UHFFFAOYSA-N 0.000 claims 1
• 125000003226 pyrazolyl group Chemical group 0.000 claims 1
• -1 polyoxyethylene Polymers 0.000 description 111
• 239000000417 fungicide Substances 0.000 description 51
• 239000003054 catalyst Substances 0.000 description 36
• 239000000306 component Substances 0.000 description 33
• 150000001336 alkenes Chemical class 0.000 description 31
• 235000013350 formula milk Nutrition 0.000 description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
• 150000001298 alcohols Chemical class 0.000 description 22
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• 238000006243 chemical reaction Methods 0.000 description 20
• 241000196324 Embryophyta Species 0.000 description 18
• 238000007037 hydroformylation reaction Methods 0.000 description 17
• 238000000034 method Methods 0.000 description 16
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 15
• 229910017052 cobalt Inorganic materials 0.000 description 15
• 239000010941 cobalt Substances 0.000 description 15
• 229910052799 carbon Inorganic materials 0.000 description 14
• GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 14
• 239000002253 acid Substances 0.000 description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
• 238000006471 dimerization reaction Methods 0.000 description 12
• 230000008569 process Effects 0.000 description 12
• 229910052751 metal Inorganic materials 0.000 description 11
• 239000002184 metal Substances 0.000 description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
• 125000002947 alkylene group Chemical group 0.000 description 10
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
• 150000007513 acids Chemical class 0.000 description 9
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• VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical class CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 8
• 239000000460 chlorine Substances 0.000 description 8
• 229910052801 chlorine Inorganic materials 0.000 description 8
• 238000009472 formulation Methods 0.000 description 8
• 238000005649 metathesis reaction Methods 0.000 description 8
• 239000003921 oil Substances 0.000 description 8
• 229910052703 rhodium Inorganic materials 0.000 description 8
• 239000010948 rhodium Substances 0.000 description 8
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
• 125000003545 alkoxy group Chemical group 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• 238000007046 ethoxylation reaction Methods 0.000 description 7
• 150000002430 hydrocarbons Chemical class 0.000 description 7
• PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
• MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 7
• 239000004094 surface-active agent Substances 0.000 description 7
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• 241000233866 Fungi Species 0.000 description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
• 239000003085 diluting agent Substances 0.000 description 6
• 150000002500 ions Chemical class 0.000 description 6
• 150000003254 radicals Chemical class 0.000 description 6
• 239000011541 reaction mixture Substances 0.000 description 6
• 150000003839 salts Chemical class 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
• UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 5
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
• 229940022663 acetate Drugs 0.000 description 5
• 150000001299 aldehydes Chemical class 0.000 description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
• 229910052794 bromium Inorganic materials 0.000 description 5
• 229910002091 carbon monoxide Inorganic materials 0.000 description 5
• 229940060037 fluorine Drugs 0.000 description 5
• 235000019000 fluorine Nutrition 0.000 description 5
• 229930195733 hydrocarbon Natural products 0.000 description 5
• 150000002431 hydrogen Chemical class 0.000 description 5
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 5
• 238000002360 preparation method Methods 0.000 description 5
• 239000007921 spray Substances 0.000 description 5
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• 229910052725 zinc Inorganic materials 0.000 description 5
• 239000011701 zinc Substances 0.000 description 5
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
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• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
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• 230000009471 action Effects 0.000 description 4
• 239000013543 active substance Substances 0.000 description 4
• 230000008901 benefit Effects 0.000 description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
• TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 4
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• 230000000875 corresponding effect Effects 0.000 description 4
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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• 230000001747 exhibiting effect Effects 0.000 description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
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• 239000000126 substance Substances 0.000 description 4
• 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 4
• 239000011573 trace mineral Substances 0.000 description 4
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• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
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