CA2938806C - Emulsifiable concentrate comprising pesticide, alkyl lactate, and lactamide - Google Patents

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Publication number

CA2938806C

CA2938806C CA2938806A CA2938806A CA2938806C CA 2938806 C CA2938806 C CA 2938806C CA 2938806 A CA2938806 A CA 2938806A CA 2938806 A CA2938806 A CA 2938806A CA 2938806 C CA2938806 C CA 2938806C

Authority

CA

Canada

Prior art keywords

weight

emulsifiable concentrate

pheny1

chloro

methyl

Prior art date

2014-02-14

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.)

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• -1 alkyl lactate Chemical compound 0.000 title claims abstract description 84
• 239000000575 pesticide Substances 0.000 title claims abstract description 71
• 239000004495 emulsifiable concentrate Substances 0.000 title claims abstract description 48
• SXQFCVDSOLSHOQ-UHFFFAOYSA-N lactamide Chemical compound CC(O)C(N)=O SXQFCVDSOLSHOQ-UHFFFAOYSA-N 0.000 title claims abstract description 38
• 244000038559 crop plants Species 0.000 claims abstract description 24
• 239000000839 emulsion Substances 0.000 claims abstract description 24
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
• 238000000034 method Methods 0.000 claims abstract description 23
• 238000002156 mixing Methods 0.000 claims abstract description 16
• 241000233866 Fungi Species 0.000 claims abstract description 13
• 239000002689 soil Substances 0.000 claims abstract description 13
• 241000238876 Acari Species 0.000 claims abstract description 12
• 241000238631 Hexapoda Species 0.000 claims abstract description 12
• 230000003032 phytopathogenic effect Effects 0.000 claims abstract description 12
• 230000001276 controlling effect Effects 0.000 claims abstract description 10
• 238000002360 preparation method Methods 0.000 claims abstract description 7
• 230000008635 plant growth Effects 0.000 claims abstract description 6
• 230000001105 regulatory effect Effects 0.000 claims abstract description 6
• 230000008569 process Effects 0.000 claims abstract description 5
• 239000000203 mixture Chemical group 0.000 claims description 47
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
• 150000001408 amides Chemical class 0.000 claims description 19
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 241001465754 Metazoa Species 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 230000001225 therapeutic effect Effects 0.000 claims description 5
• SFBIZPBTKROSDE-UHFFFAOYSA-N octyl 2-hydroxypropanoate Chemical compound CCCCCCCCOC(=O)C(C)O SFBIZPBTKROSDE-UHFFFAOYSA-N 0.000 claims description 4
• FECDACOUYKFOOP-UHFFFAOYSA-N 2-ethylhexyl 2-hydroxypropanoate Chemical compound CCCCC(CC)COC(=O)C(C)O FECDACOUYKFOOP-UHFFFAOYSA-N 0.000 claims description 2
• 239000012141 concentrate Substances 0.000 abstract description 59
• 241000607479 Yersinia pestis Species 0.000 abstract description 7
• 239000003112 inhibitor Substances 0.000 description 28
• 150000001875 compounds Chemical class 0.000 description 23
• 240000008042 Zea mays Species 0.000 description 16
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 16
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 16
• 235000005822 corn Nutrition 0.000 description 16
• 239000013078 crystal Substances 0.000 description 16
• 239000000178 monomer Substances 0.000 description 15
• 239000002904 solvent Substances 0.000 description 15
• 239000004215 Carbon black (E152) Substances 0.000 description 13
• 239000002736 nonionic surfactant Substances 0.000 description 13
• 235000014113 dietary fatty acids Nutrition 0.000 description 12
• 229920000642 polymer Polymers 0.000 description 12
• 150000003871 sulfonates Chemical class 0.000 description 12
• 239000000194 fatty acid Substances 0.000 description 11
• 229930195729 fatty acid Natural products 0.000 description 11
• 239000000417 fungicide Substances 0.000 description 11
• 229930195733 hydrocarbon Natural products 0.000 description 11
• 150000002430 hydrocarbons Chemical class 0.000 description 11
• 239000004094 surface-active agent Substances 0.000 description 10
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
• 241000196324 Embryophyta Species 0.000 description 9
• 239000005788 Fluxapyroxad Substances 0.000 description 9
• 239000005822 Propiconazole Substances 0.000 description 9
• 230000015572 biosynthetic process Effects 0.000 description 9
• 229920001577 copolymer Polymers 0.000 description 9
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
• SXSGXWCSHSVPGB-UHFFFAOYSA-N fluxapyroxad Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(F)=C(F)C(F)=C1 SXSGXWCSHSVPGB-UHFFFAOYSA-N 0.000 description 9
• STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 9
• 239000003945 anionic surfactant Substances 0.000 description 8
• 150000004665 fatty acids Chemical class 0.000 description 8
• 229920000867 polyelectrolyte Polymers 0.000 description 8
• 239000005760 Difenoconazole Substances 0.000 description 7
• BQYJATMQXGBDHF-UHFFFAOYSA-N difenoconazole Chemical compound O1C(C)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 BQYJATMQXGBDHF-UHFFFAOYSA-N 0.000 description 7
• 238000009472 formulation Methods 0.000 description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
• ZVXKYWHJBYIYNI-UHFFFAOYSA-N 1h-pyrazole-4-carboxamide Chemical compound NC(=O)C=1C=NNC=1 ZVXKYWHJBYIYNI-UHFFFAOYSA-N 0.000 description 6
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
• 239000002671 adjuvant Substances 0.000 description 6
• 125000000217 alkyl group Chemical group 0.000 description 6
• 150000002193 fatty amides Chemical class 0.000 description 6
• 238000011049 filling Methods 0.000 description 6
• 150000003839 salts Chemical class 0.000 description 6
• 239000007921 spray Substances 0.000 description 6
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 5
• CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
• 239000005869 Pyraclostrobin Substances 0.000 description 5
• BTANRVKWQNVYAZ-UHFFFAOYSA-N Sec-butyl alcohol Natural products CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 5
• 239000013543 active substance Substances 0.000 description 5
• YXXPNGIZHZHBTQ-UHFFFAOYSA-N butan-2-ol Chemical compound CC[C](C)O YXXPNGIZHZHBTQ-UHFFFAOYSA-N 0.000 description 5
• 239000003086 colorant Substances 0.000 description 5
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
• 239000002917 insecticide Substances 0.000 description 5
• KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 5
• 239000000463 material Substances 0.000 description 5
• 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 description 5
• 150000003467 sulfuric acid derivatives Chemical class 0.000 description 5
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 4
• 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 4
• XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
• 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
• 150000001298 alcohols Chemical class 0.000 description 4
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
• MBHXIQDIVCJZTD-RVDMUPIBSA-N flufenoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=C(C(F)(F)F)C=C1Cl MBHXIQDIVCJZTD-RVDMUPIBSA-N 0.000 description 4
• 239000003630 growth substance Substances 0.000 description 4
• 239000004009 herbicide Substances 0.000 description 4
• 239000007788 liquid Substances 0.000 description 4
• 239000000047 product Substances 0.000 description 4
• 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 description 4
• 239000000243 solution Substances 0.000 description 4
• 238000005507 spraying Methods 0.000 description 4
• 238000003786 synthesis reaction Methods 0.000 description 4
• QFNFRZHOXWNWAQ-UHFFFAOYSA-N triclopyricarb Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NC(Cl)=C(Cl)C=C1Cl QFNFRZHOXWNWAQ-UHFFFAOYSA-N 0.000 description 4
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 3
• 102000015782 Electron Transport Complex III Human genes 0.000 description 3
• 108010024882 Electron Transport Complex III Proteins 0.000 description 3
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• 229940123669 Mitochondrial electron transport inhibitor Drugs 0.000 description 3
• NWBJYWHLCVSVIJ-UHFFFAOYSA-N N-benzyladenine Chemical compound N=1C=NC=2NC=NC=2C=1NCC1=CC=CC=C1 NWBJYWHLCVSVIJ-UHFFFAOYSA-N 0.000 description 3
• 229910019142 PO4 Inorganic materials 0.000 description 3
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• 229910052799 carbon Inorganic materials 0.000 description 3
• 239000003795 chemical substances by application Substances 0.000 description 3
• 239000012895 dilution Substances 0.000 description 3
• 238000010790 dilution Methods 0.000 description 3
• QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 3
• 238000002474 experimental method Methods 0.000 description 3
• NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 3
• 235000019198 oils Nutrition 0.000 description 3
• JTHLRRZARWSHBE-UHFFFAOYSA-N pent-4-yn-2-ol Chemical compound CC(O)CC#C JTHLRRZARWSHBE-UHFFFAOYSA-N 0.000 description 3
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
• 235000021317 phosphate Nutrition 0.000 description 3
• 150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
• 229920006395 saturated elastomer Polymers 0.000 description 3
• 238000003756 stirring Methods 0.000 description 3
• ROZUQUDEWZIBHV-UHFFFAOYSA-N tecloftalam Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(=O)NC1=CC=CC(Cl)=C1Cl ROZUQUDEWZIBHV-UHFFFAOYSA-N 0.000 description 3
• 150000003852 triazoles Chemical class 0.000 description 3
• YNWVFADWVLCOPU-MDWZMJQESA-N (1E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1/C(C(O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MDWZMJQESA-N 0.000 description 2
• KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
• IAQLCKZJGNTRDO-UHFFFAOYSA-N 1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2CC(ON=2)C=2C(=CC=CC=2F)F)CC1 IAQLCKZJGNTRDO-UHFFFAOYSA-N 0.000 description 2
• PFFIDZXUXFLSSR-UHFFFAOYSA-N 1-methyl-N-[2-(4-methylpentan-2-yl)-3-thienyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound S1C=CC(NC(=O)C=2C(=NN(C)C=2)C(F)(F)F)=C1C(C)CC(C)C PFFIDZXUXFLSSR-UHFFFAOYSA-N 0.000 description 2
• 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 2
• WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
• XTDZGXBTXBEZDN-UHFFFAOYSA-N 3-(difluoromethyl)-N-(9-isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl)-1-methylpyrazole-4-carboxamide Chemical compound CC(C)C1C2CCC1C1=C2C=CC=C1NC(=O)C1=CN(C)N=C1C(F)F XTDZGXBTXBEZDN-UHFFFAOYSA-N 0.000 description 2
• BMTZEAOGFDXDAD-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride Chemical compound [Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 BMTZEAOGFDXDAD-UHFFFAOYSA-M 0.000 description 2
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
• NRTLIYOWLVMQBO-UHFFFAOYSA-N 5-chloro-1,3-dimethyl-N-(1,1,3-trimethyl-1,3-dihydro-2-benzofuran-4-yl)pyrazole-4-carboxamide Chemical compound C=12C(C)OC(C)(C)C2=CC=CC=1NC(=O)C=1C(C)=NN(C)C=1Cl NRTLIYOWLVMQBO-UHFFFAOYSA-N 0.000 description 2
• GOFJDXZZHFNFLV-UHFFFAOYSA-N 5-fluoro-1,3-dimethyl-N-[2-(4-methylpentan-2-yl)phenyl]pyrazole-4-carboxamide Chemical compound CC(C)CC(C)C1=CC=CC=C1NC(=O)C1=C(F)N(C)N=C1C GOFJDXZZHFNFLV-UHFFFAOYSA-N 0.000 description 2
• PCCSBWNGDMYFCW-UHFFFAOYSA-N 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(C)(C=2C=CC(OC=3C=CC=CC=3)=CC=2)OC(=O)N1NC1=CC=CC=C1 PCCSBWNGDMYFCW-UHFFFAOYSA-N 0.000 description 2
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• 239000005738 Bixafen Substances 0.000 description 2
• 239000005740 Boscalid Substances 0.000 description 2
• 239000005746 Carboxin Substances 0.000 description 2
• LBGPXIPGGRQBJW-UHFFFAOYSA-N Difenzoquat Chemical compound C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 LBGPXIPGGRQBJW-UHFFFAOYSA-N 0.000 description 2
• 239000005762 Dimoxystrobin Substances 0.000 description 2
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
• 239000005772 Famoxadone Substances 0.000 description 2
• 239000005774 Fenamidone Substances 0.000 description 2
• 239000005898 Fenoxycarb Substances 0.000 description 2
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• 239000005562 Glyphosate Substances 0.000 description 2
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
• 101000615488 Homo sapiens Methyl-CpG-binding domain protein 2 Proteins 0.000 description 2
• UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
• 239000005798 Isofetamid Substances 0.000 description 2
• 239000005799 Isopyrazam Substances 0.000 description 2
• 239000005800 Kresoxim-methyl Substances 0.000 description 2
• JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
• VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
• 102100021299 Methyl-CpG-binding domain protein 2 Human genes 0.000 description 2
• WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
• CCCGEKHKTPTUHJ-UHFFFAOYSA-N N-[9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC2=C1C1CCC2C1=C(Cl)Cl CCCGEKHKTPTUHJ-UHFFFAOYSA-N 0.000 description 2
• XQJQCBDIXRIYRP-UHFFFAOYSA-N N-{2-[1,1'-bi(cyclopropyl)-2-yl]phenyl}-3-(difluoromethyl)-1-methyl-1pyrazole-4-carboxamide Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1C(C2CC2)C1 XQJQCBDIXRIYRP-UHFFFAOYSA-N 0.000 description 2
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• CJPQIRJHIZUAQP-MRXNPFEDSA-N benalaxyl-M Chemical compound CC=1C=CC=C(C)C=1N([C@H](C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-MRXNPFEDSA-N 0.000 description 2
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• 230000004071 biological effect Effects 0.000 description 2
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• 229960003168 bronopol Drugs 0.000 description 2
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• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
• 150000003857 carboxamides Chemical class 0.000 description 2
• GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 description 2
• 150000007942 carboxylates Chemical class 0.000 description 2
• 239000004359 castor oil Substances 0.000 description 2
• 235000019438 castor oil Nutrition 0.000 description 2
• 239000003093 cationic surfactant Substances 0.000 description 2
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