CA2245537C - Compositions herbicides stables contenant des chelates de metal de composes herbicides diones - Google Patents
Compositions herbicides stables contenant des chelates de metal de composes herbicides diones Download PDFInfo
- Publication number
- CA2245537C CA2245537C CA 2245537 CA2245537A CA2245537C CA 2245537 C CA2245537 C CA 2245537C CA 2245537 CA2245537 CA 2245537 CA 2245537 A CA2245537 A CA 2245537A CA 2245537 C CA2245537 C CA 2245537C
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- group containing
- optionally substituted
- halogen
- alkyl
- 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
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- 239000000203 mixture Substances 0.000 title claims abstract description 123
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 98
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 72
- 239000002184 metal Substances 0.000 title claims abstract description 72
- 150000001875 compounds Chemical class 0.000 title claims abstract description 70
- 239000007788 liquid Substances 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 24
- 239000004009 herbicide Substances 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 85
- 125000000217 alkyl group Chemical group 0.000 claims description 64
- 125000005843 halogen group Chemical group 0.000 claims description 58
- 239000013522 chelant Substances 0.000 claims description 46
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
- -1 cyano, phenyl Chemical group 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 229910052723 transition metal Inorganic materials 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 150000003624 transition metals Chemical class 0.000 claims description 6
- 239000012266 salt solution Substances 0.000 claims description 5
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 4
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 claims description 4
- 239000005489 Bromoxynil Substances 0.000 claims description 4
- 239000005574 MCPA Substances 0.000 claims description 4
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 4
- 150000008061 acetanilides Chemical class 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 239000005624 Tralkoxydim Substances 0.000 claims description 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- OLZQTUCTGLHFTQ-UHFFFAOYSA-N octan-2-yl 2-(4-amino-3,5-dichloro-6-fluoropyridin-2-yl)oxyacetate Chemical group CCCCCCC(C)OC(=O)COC1=NC(F)=C(Cl)C(N)=C1Cl OLZQTUCTGLHFTQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 claims description 3
- LDRGJXWZXUGHER-UHFFFAOYSA-N 2-(4-chloro-2-methylsulfonylbenzoyl)-3-cyclopropyl-3-oxopropanenitrile Chemical compound CS(=O)(=O)C1=CC(Cl)=CC=C1C(=O)C(C#N)C(=O)C1CC1 LDRGJXWZXUGHER-UHFFFAOYSA-N 0.000 claims description 2
- ZTTKDUXKVPEXCG-UHFFFAOYSA-N 2-cyano-3-cyclopropyl-1-(2-mesyl-4-trifluoromethylphenyl)propan-1,3-dione Chemical compound CS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1C(=O)C(C#N)C(=O)C1CC1 ZTTKDUXKVPEXCG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 18
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 2
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims 2
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims 2
- 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 claims 2
- KPUREKXXPHOJQT-UHFFFAOYSA-N mesotrione Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O KPUREKXXPHOJQT-UHFFFAOYSA-N 0.000 claims 2
- JEAYJWVIAQIJHS-UHFFFAOYSA-N 2-(2-chloro-3-ethoxy-4-ethylsulfonylbenzoyl)-3-cyclopropyl-3-oxopropanenitrile Chemical compound C1=C(S(=O)(=O)CC)C(OCC)=C(Cl)C(C(=O)C(C#N)C(=O)C2CC2)=C1 JEAYJWVIAQIJHS-UHFFFAOYSA-N 0.000 claims 1
- DUDUWVJPQXZLJZ-UHFFFAOYSA-N 2-(4-bromo-2-methylsulfonylbenzoyl)-3-cyclopropyl-3-oxopropanenitrile Chemical compound CS(=O)(=O)C1=CC(Br)=CC=C1C(=O)C(C#N)C(=O)C1CC1 DUDUWVJPQXZLJZ-UHFFFAOYSA-N 0.000 claims 1
- MAPXZHNGBCCSFO-UHFFFAOYSA-N [4-(2,6-dioxocyclohexanecarbonyl)-3-nitrophenyl] methanesulfonate Chemical compound [O-][N+](=O)C1=CC(OS(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O MAPXZHNGBCCSFO-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000003801 milling Methods 0.000 claims 1
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 claims 1
- 238000009472 formulation Methods 0.000 abstract description 64
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 description 32
- 239000000126 substance Substances 0.000 description 29
- 238000003860 storage Methods 0.000 description 26
- 239000010949 copper Substances 0.000 description 24
- 239000008346 aqueous phase Substances 0.000 description 19
- 229910052802 copper Inorganic materials 0.000 description 18
- 229910021645 metal ion Inorganic materials 0.000 description 18
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000004480 active ingredient Substances 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 239000008187 granular material Substances 0.000 description 8
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000001188 haloalkyl group Chemical group 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000012669 liquid formulation Substances 0.000 description 5
- 239000003094 microcapsule Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000000969 carrier Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000013068 control sample Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000012430 stability testing Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 230000006978 adaptation Effects 0.000 description 3
- 239000013011 aqueous formulation Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000009920 chelation Effects 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000013020 final formulation Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000011369 resultant mixture Substances 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 229910001428 transition metal ion Inorganic materials 0.000 description 3
- 240000006995 Abutilon theophrasti Species 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 description 2
- 244000152970 Digitaria sanguinalis Species 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- 244000020551 Helianthus annuus Species 0.000 description 2
- 235000003222 Helianthus annuus Nutrition 0.000 description 2
- 240000007218 Ipomoea hederacea Species 0.000 description 2
- 241000441237 Lolium lowei Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 235000007199 Panicum miliaceum Nutrition 0.000 description 2
- 244000234609 Portulaca oleracea Species 0.000 description 2
- 235000001855 Portulaca oleracea Nutrition 0.000 description 2
- 240000006394 Sorghum bicolor Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 244000067505 Xanthium strumarium Species 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229960000892 attapulgite Drugs 0.000 description 2
- 244000022203 blackseeded proso millet Species 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
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- 230000009969 flowable effect Effects 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 125000004438 haloalkoxy group Chemical group 0.000 description 2
- 229910003480 inorganic solid Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000004519 manufacturing process Methods 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
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- 239000008096 xylene Substances 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZOGDSYNXUXQGHF-XIEYBQDHSA-N Butroxydim Chemical compound CCCC(=O)C1=C(C)C=C(C)C(C2CC(=O)C(\C(CC)=N\OCC)=C(O)C2)=C1C ZOGDSYNXUXQGHF-XIEYBQDHSA-N 0.000 description 1
- 101100008046 Caenorhabditis elegans cut-2 gene Proteins 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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- 239000004375 Dextrin Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 235000003403 Limnocharis flava Nutrition 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
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- 235000006923 Sorghum x drummondii Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
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- 150000001412 amines Chemical class 0.000 description 1
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- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
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- 229910000365 copper sulfate Inorganic materials 0.000 description 1
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- 229960003280 cupric chloride Drugs 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
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- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
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- 229910052731 fluorine Inorganic materials 0.000 description 1
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- OUBCNLGXQFSTLU-UHFFFAOYSA-N nitisinone Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1C(=O)C1C(=O)CCCC1=O OUBCNLGXQFSTLU-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
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- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000008654 plant damage Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Chélates de métal de composés herbicides diones représenté par la formule (I). Ces chélates sont chimiquement stables pendant des durées prolongées dans des conditions de température normales ou extrêmes. L'invention concerne également des formulations herbicides liquides chimiquement stables contenant des chélates de métal des composés herbicides représentés par la formule (I), de l'eau, un solvant organique ou un herbicide liquide associé, ainsi que des procédés servant à préparer des compositions herbicides chimiquement stables contenant ces chélates de métal.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59560596A | 1996-02-02 | 1996-02-02 | |
| US08/595,605 | 1996-02-02 | ||
| PCT/GB1997/000302 WO1997027748A1 (fr) | 1996-02-02 | 1997-02-03 | Compositions herbicides stables contenant des chelates de metal de composes herbicides diones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2245537A1 CA2245537A1 (fr) | 1997-08-07 |
| CA2245537C true CA2245537C (fr) | 2006-10-17 |
Family
ID=29422182
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2245537 Expired - Lifetime CA2245537C (fr) | 1996-02-02 | 1997-02-03 | Compositions herbicides stables contenant des chelates de metal de composes herbicides diones |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2245537C (fr) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9206381B2 (en) | 2011-09-21 | 2015-12-08 | Ecolab Usa Inc. | Reduced misting alkaline cleaners using elongational viscosity modifiers |
| US9637708B2 (en) | 2014-02-14 | 2017-05-02 | Ecolab Usa Inc. | Reduced misting and clinging chlorine-based hard surface cleaner |
| US10370626B2 (en) | 2016-05-23 | 2019-08-06 | Ecolab Usa Inc. | Reduced misting acidic cleaning, sanitizing, and disinfecting compositions via the use of high molecular weight water-in-oil emulsion polymers |
| US10392587B2 (en) | 2016-05-23 | 2019-08-27 | Ecolab Usa Inc. | Reduced misting alkaline and neutral cleaning, sanitizing, and disinfecting compositions via the use of high molecular weight water-in-oil emulsion polymers |
| US11540512B2 (en) | 2017-03-01 | 2023-01-03 | Ecolab Usa Inc. | Reduced inhalation hazard sanitizers and disinfectants via high molecular weight polymers |
| US11834633B2 (en) | 2019-07-12 | 2023-12-05 | Ecolab Usa Inc. | Reduced mist alkaline cleaner via the use of alkali soluble emulsion polymers |
-
1997
- 1997-02-03 CA CA 2245537 patent/CA2245537C/fr not_active Expired - Lifetime
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9206381B2 (en) | 2011-09-21 | 2015-12-08 | Ecolab Usa Inc. | Reduced misting alkaline cleaners using elongational viscosity modifiers |
| US9637708B2 (en) | 2014-02-14 | 2017-05-02 | Ecolab Usa Inc. | Reduced misting and clinging chlorine-based hard surface cleaner |
| US10220421B2 (en) | 2014-02-14 | 2019-03-05 | Ecolab Usa Inc. | Reduced misting and clinging chlorine-based hard surface cleaner |
| US10821484B2 (en) | 2014-02-14 | 2020-11-03 | Ecolab Usa Inc. | Reduced misting and clinging chlorine-based hard surface cleaner |
| US11331696B2 (en) | 2014-02-14 | 2022-05-17 | Ecolab Usa Inc. | Reduced misting and clinging chlorine based hard surface cleaner |
| US10370626B2 (en) | 2016-05-23 | 2019-08-06 | Ecolab Usa Inc. | Reduced misting acidic cleaning, sanitizing, and disinfecting compositions via the use of high molecular weight water-in-oil emulsion polymers |
| US10392587B2 (en) | 2016-05-23 | 2019-08-27 | Ecolab Usa Inc. | Reduced misting alkaline and neutral cleaning, sanitizing, and disinfecting compositions via the use of high molecular weight water-in-oil emulsion polymers |
| US11008538B2 (en) | 2016-05-23 | 2021-05-18 | Ecolab Usa Inc. | Reduced misting alkaline and neutral cleaning, sanitizing, and disinfecting compositions via the use of high molecular weight water-in-oil emulsion polymers |
| US11540512B2 (en) | 2017-03-01 | 2023-01-03 | Ecolab Usa Inc. | Reduced inhalation hazard sanitizers and disinfectants via high molecular weight polymers |
| US11834633B2 (en) | 2019-07-12 | 2023-12-05 | Ecolab Usa Inc. | Reduced mist alkaline cleaner via the use of alkali soluble emulsion polymers |
| US12281286B2 (en) | 2019-07-12 | 2025-04-22 | Ecolab Usa Inc. | Reduced mist alkaline cleaner via the use of alkali soluble emulsion polymers |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2245537A1 (fr) | 1997-08-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20170203 |