US20010051145A1 - Copolymers and their use as drift control agents - Google Patents
Copolymers and their use as drift control agents Download PDFInfo
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- US20010051145A1 US20010051145A1 US09/784,536 US78453601A US2001051145A1 US 20010051145 A1 US20010051145 A1 US 20010051145A1 US 78453601 A US78453601 A US 78453601A US 2001051145 A1 US2001051145 A1 US 2001051145A1
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- 239000000178 monomer Substances 0.000 claims abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 239000001301 oxygen Substances 0.000 claims abstract description 10
- 230000003252 repetitive effect Effects 0.000 claims abstract description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004437 phosphorous atom Chemical group 0.000 claims abstract description 7
- 229910052698 phosphorus Chemical group 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 239000011593 sulfur Chemical group 0.000 claims abstract description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 5
- 238000004132 cross linking Methods 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 239000000575 pesticide Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 5
- 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 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 11
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 14
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- 239000002253 acid Substances 0.000 description 9
- 0 *#*(=O)(NC(=O)C(CC)CC)=S(=O)=O.C.C Chemical compound *#*(=O)(NC(=O)C(CC)CC)=S(=O)=O.C.C 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
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- 150000002148 esters Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
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- 239000002245 particle Substances 0.000 description 3
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- QENRKQYUEGJNNZ-UHFFFAOYSA-N 2-methyl-1-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound CC(C)C(S(O)(=O)=O)NC(=O)C=C QENRKQYUEGJNNZ-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- NPNVICDFKJTBPY-UHFFFAOYSA-N C.C.CCC(C)(C)C(=O)N(C)C Chemical compound C.C.CCC(C)(C)C(=O)N(C)C NPNVICDFKJTBPY-UHFFFAOYSA-N 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- QYPPRTNMGCREIM-UHFFFAOYSA-N methylarsonic acid Chemical compound C[As](O)(O)=O QYPPRTNMGCREIM-UHFFFAOYSA-N 0.000 description 2
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 2
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 description 2
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
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- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 239000000230 xanthan gum Substances 0.000 description 2
- 229920001285 xanthan gum Polymers 0.000 description 2
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- 229940082509 xanthan gum Drugs 0.000 description 2
- GXEKYRXVRROBEV-FBXFSONDSA-N (1r,2s,3r,4s)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid Chemical compound C1C[C@@H]2[C@@H](C(O)=O)[C@@H](C(=O)O)[C@H]1O2 GXEKYRXVRROBEV-FBXFSONDSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-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-JGWLITMVSA-N 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 description 1
- CYIGRWUIQAVBFG-UHFFFAOYSA-N 1,2-bis(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOCCOC=C CYIGRWUIQAVBFG-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
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- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- MZHCENGPTKEIGP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-UHFFFAOYSA-N 0.000 description 1
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 1
- NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 description 1
- CLQMBPJKHLGMQK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=CC=C1C(O)=O CLQMBPJKHLGMQK-UHFFFAOYSA-N 0.000 description 1
- GOCUAJYOYBLQRH-UHFFFAOYSA-N 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl GOCUAJYOYBLQRH-UHFFFAOYSA-N 0.000 description 1
- YUVKUEAFAVKILW-UHFFFAOYSA-N 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 YUVKUEAFAVKILW-UHFFFAOYSA-N 0.000 description 1
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- 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 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
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- GQQIAHNFBAFBCS-UHFFFAOYSA-N 2-[2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)-4-fluorophenoxy]acetic acid Chemical compound C1=C(Cl)C(OCC(=O)O)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F GQQIAHNFBAFBCS-UHFFFAOYSA-N 0.000 description 1
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- MPPOHAUSNPTFAJ-UHFFFAOYSA-N 2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 MPPOHAUSNPTFAJ-UHFFFAOYSA-N 0.000 description 1
- CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 description 1
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- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 1
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- 239000005595 Picloram Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
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- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000012271 agricultural production Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- VGPYEHKOIGNJKV-UHFFFAOYSA-N asulam Chemical compound COC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VGPYEHKOIGNJKV-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 208000014347 autosomal dominant hyaline body myopathy Diseases 0.000 description 1
- OTSAMNSACVKIOJ-UHFFFAOYSA-N azane;carbamoyl(ethoxy)phosphinic acid Chemical compound [NH4+].CCOP([O-])(=O)C(N)=O OTSAMNSACVKIOJ-UHFFFAOYSA-N 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 description 1
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 1
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- 239000001110 calcium chloride Substances 0.000 description 1
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- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
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- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
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- 239000003638 chemical reducing agent Substances 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
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- 125000005131 dialkylammonium group Chemical group 0.000 description 1
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- GQOKIYDTHHZSCJ-UHFFFAOYSA-M dimethyl-bis(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C=CC[N+](C)(C)CC=C GQOKIYDTHHZSCJ-UHFFFAOYSA-M 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
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- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
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- 238000001914 filtration Methods 0.000 description 1
- BGZZWXTVIYUUEY-UHFFFAOYSA-N fomesafen Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)C)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 BGZZWXTVIYUUEY-UHFFFAOYSA-N 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
- 229940097068 glyphosate Drugs 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate 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
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 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
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- WXUNXXKSYBUHMK-UHFFFAOYSA-N methyl 4-methyl-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoate;methyl 5-methyl-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoate Chemical compound COC(=O)C1=CC=C(C)C=C1C1=NC(C)(C(C)C)C(=O)N1.COC(=O)C1=CC(C)=CC=C1C1=NC(C)(C(C)C)C(=O)N1 WXUNXXKSYBUHMK-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical group COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- NDNKHWUXXOFHTD-UHFFFAOYSA-N metizoline Chemical compound CC=1SC2=CC=CC=C2C=1CC1=NCCN1 NDNKHWUXXOFHTD-UHFFFAOYSA-N 0.000 description 1
- 229960002939 metizoline Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- JITOKQVGRJSHHA-UHFFFAOYSA-M monosodium methyl arsenate Chemical compound [Na+].C[As](O)([O-])=O JITOKQVGRJSHHA-UHFFFAOYSA-M 0.000 description 1
- OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-UHFFFAOYSA-N 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 1
- SHIGCAOWAAOWIG-UHFFFAOYSA-N n-prop-2-enylformamide Chemical compound C=CCNC=O SHIGCAOWAAOWIG-UHFFFAOYSA-N 0.000 description 1
- JXTHEWSKYLZVJC-UHFFFAOYSA-N naptalam Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1=CC=CC2=CC=CC=C12 JXTHEWSKYLZVJC-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 239000003090 pesticide formulation Substances 0.000 description 1
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920001510 poly[2-(diisopropylamino)ethyl methacrylate] polymer Polymers 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- 239000003128 rodenticide Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000019351 sodium silicates Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 229940075554 sorbate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 230000008719 thickening 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
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 1
- UZNHKBFIBYXPDV-UHFFFAOYSA-N trimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)NCCC[N+](C)(C)C UZNHKBFIBYXPDV-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000007966 viscous suspension Substances 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
- A01N25/10—Macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
- C08F220/585—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine and containing other heteroatoms, e.g. 2-acrylamido-2-methylpropane sulfonic acid [AMPS]
Definitions
- the present invention relates to the use of water-soluble or water-swellable copolymers based on acrylamidoalkylsulfonic acid salts as drift control agents in crop protection compositions.
- Pesticides are applied in a highly efficient manner to agricultural production fields using spray tanks in airplanes, tractors and other devices. To achieve an application of the active substances which is as accurate as possible, it is necessary to obtain a spray cone which is as narrow as possible, and to avoid a drift of the spray mist from the target area.
- the drift of the spray cone is determined substantially by the droplet size.
- the drift effect can be reduced considerably by adding suitable drift control agents to pesticide formulations, which drift control agents increase the size of the droplets in the spray mist.
- the formulations modified by drift control agents additionally have to be insensitive to shear forces to which they are exposed in the spray pumps and nozzles. Drift control agents are furthermore required to have good biological degradability, compatibility with the other components of the crop protection composition and high storage and temperature stability.
- aqueous compositions can be modified by adding water-soluble polymers, for example polyacrylamides, acrylamide/acrylic acid polymers, sodium polyacrylate, carboxymethylcellulose, hydroxyethylcellulose, methylcellulose, polysaccharides and natural and synthetic guar gum
- water-soluble polymers for example polyacrylamides, acrylamide/acrylic acid polymers, sodium polyacrylate, carboxymethylcellulose, hydroxyethylcellulose, methylcellulose, polysaccharides and natural and synthetic guar gum
- the invention provides copolymers consisting essentially of from 1 to 90% by weight of the repetitive structural unit of the formula (1)
- R 1 is hydrogen or methyl
- Z is a C 1 -C 4 -alkylene group
- X is hydrogen, an alkali metal or ammonium, from 10 to 99% by weight of a repetitive structural unit which is derived from olefinically unsaturated comonomers containing at least one oxygen, nitrogen, sulfur or phosphorus atom and from 0 to 20% by weight of crosslinking structures originating from monomers having at least two olefinic double bonds.
- R 2 hydrogen or methyl
- R 3 C 1 -C 22 -alkylene
- R 4 C 1 -C 22 -alkyl or hydrogen
- X ammonium, lithium, sodium, potassium, an amine or a mixture of these substances and 99-1% by weight of structural units of the formula (3)
- R 5 hydrogen or methyl
- R 6 and R 7 independently of one another are hydrogen or C 2 -C 22 -alkyl.
- the preferred monomer of the formula (1) is 2-acrylamido-2-methylpropanesulfonic acid and its salts, preferably the ammonium salt.
- Suitable olefinically unsaturated monomers containing at least one oxygen, nitrogen, sulfur or phosphorus atom are, for example, styrenesulfonic acid, acrylamidopropylmethylenesulfonic acid (AMPS), vinylsulfonic acid, vinylphosphonic acid, allylsulfonic acid, methallylsulfonic acid, acrylic acid, methacrylic acid and maleic acid (and its anhydride) and the salts of the acids mentioned above with mono- and divalent counterions.
- Preferred counterions are lithium, sodium, potassium, magnesium, calcium, ammonium, monoalkylammonium, dialkylammonium, trialkylammonium or tetraalkylammonium, where the alkyl substituents of the amines independently of one another are C 1 -C 22 -alkyl radicals which may be substituted by 0 to 3 hydroxyalkyl groups, the alkyl chain length of which may vary in a range from C 2 -C 10 . Additionally, it is also possible to use mono- to triethoxylated ammonium compounds with a different degree of ethoxylation. Particularly preferred counterions are sodium and ammonium.
- the degree of neutralization of the mole fraction of the acids described above may also differ from 100%. Suitable are all degrees of neutralization between 0 and 100%, the range between 70 and 100% being particularly preferred.
- esters of acrylic or methacrylic acid with aliphatic, aromatic or cycloaliphatic alcohols having a carbon number of C 1 -C 22 , open-chain or cyclic are suitable.
- N-vinylamides (vinyllactams) of a ring size of from 3 to 9, for example N-vinylformamide (VIFA), N-vinylmethylformamide, N-vinylmethylacetamide (VIMA), N-vinylacetamide, N-vinylpyrrolidone (NVP) and N-vinylcaprolactam.
- VFA N-vinylformamide
- VIMA N-vinylmethylacetamide
- N-vinylacetamide N-vinylpyrrolidone
- N-vinylcaprolactam N-vinylcaprolactam.
- Amides of acrylic or methacrylic acid can also be used as monomers. Examples which may be mentioned are, inter alia, acrylamide, N,N-dimethylacrylamide, N,N-diethylacrylamide, methacrylamide, alkoxylated acrylamides or methacrylamides (for example MAPTAC, APTAC).
- Suitable monomers are 2- and 4-vinylpyridine, vinyl acetate, glycidyl methacrylate, acrylonitrile, vinylphosphonic acid and esters or alkali metal, alkaline earth metal or ammonium salts thereof, DADMAC and vinylsulphonic acid or its corresponding Na + , K + , Li + , Mg 2+ or Ca 2+ salts. It is, of course, also possible for combinations of the monomers listed to be present. As already mentioned, the sum of the comonomers used can be from 9.99 to 98.99% of the total mass of the polymer.
- the polymers used according to the invention as drift control agents in crop protection compositions can be crosslinked, i.e.
- Suitable crosslinkers are, in particular, methylenebisacrylamide or methylenebismethacrylamide, esters of unsaturated mono- or polycarboxylic acids of polyols, such as diacrylate or triacrylate or methacrylates, for example butanediol or ethylene glycol diacrylate or methacrylate, and also trimethylolpropane tri(meth)acrylate and allyl compounds, such as allyl (meth)acrylate, triallyl cyanurate, diallyl maleate, polyallyl esters, tetraallyloxyethane, triallylamine, tetraallylethylenediamine, allyl esters of phosphoric acid and derivatives of vinylphosphonic acid, furthermore, allyl or vinyl ethers, for example dipropylene glycol diallyl ether, polyglycol diallyl ether, triethylene glycol divinyl ether, hydroquinone dial
- the polymers according to the invention are prepared by free-radical copolymerization in C 1 -C 6 -alcohols, preferably in tert-butanol.
- the polymerization can be carried out at in a temperature range of from 0 to 150° C., preferably between 10 and 100° C., and at atmospheric pressure or else under elevated or reduced pressure. As usual, the polymerization can also be carried out in an atmosphere of protective gas, preferably under nitrogen.
- the customary chemical polymerization initiators for example organic or inorganic peroxides, such as benzoyl peroxide, tert-butyl hydroperoxide, methylene ketone peroxide, cumene hydroperoxide, azo compounds, such as, for example, azodiisobutyronitrile, and also inorganic peroxy compounds, such as (NH 4 ) 2 S 2 O 8 or K 2 S 2 O 8 or H 2 O 2 , if appropriate in combination with reducing agents, such as sodium hydrogen sulfite and iron(II) sulfate or redox systems which, as reducing component, comprise an aliphatic or aromatic sulfonic acid, such as benzenesulfonic acid and toluenesulfonic acid, or derivatives of these acids, such as, for example, Mannich adducts of sulfinic acid, aldehydes and
- the polymers have a number-average molecular weight of from 1000 to 20 000 000 g/mol. Preference is given to a molecular weight of from 20 000 to 5 000 000, in particular 100 000 to 1 500 000 g/mol.
- the invention provides furthermore pesticide preparations comprising a copolymer of repetitive structural units of the formula (1), of structural units which are derived from olefinically unsaturated compounds containing an oxygen, nitrogen, sulfur or phosphorus atom and crosslinking structures as described above.
- These pesticide preparations may also comprise copolymers of the monomers of the formulae (2) and (3).
- the pesticide preparations comprise the customary active compounds, such as herbicides, insecticides, fungicides, acaricides, bactericides, molluscides, nematicides or rodenticides. Preference is given to herbicidal preparations.
- Suitable herbicidally active compounds are in particular glyphosate, but also acifluorfen, asulam, benazolin, bentazone, bilanafos, bromacil, bromoxynil, chloramben, clopyralid, 2,4-D, 2,4-DB, dalapon, dicamba, dichlorprop, diclofop, endothall, fenach, fenoxaprop, glamprop, fluazifop, flumiclorac, fluoroglacofen, fomesafen, fosamine, glufosinate, haloxyfop, imazapic, imazamethabenz, imazamox, imazapyr, imazaquin, imazethapyr, ioxynil, MCPA, MCPB, mecoprop, methylarsonic acid/MSMA, naptalam, picloram, quinclorac, quizalofop, 2,3,6-TBS-TCA.
- the preparations according to the invention may comprise the copolymers based on acrylamidoalkylsulfonic acid salts as drift control agents in virtually any amount. Preference is given to the following preparations:
- Formulations as tank-mix and ready-to-use compositions comprise from 0.01 to 10% by weight, preferably from 0.0025 to 2% by weight, of pesticide and from 0.0001% by weight to 5% by weight, preferably from 0.0025 to 2%, particularly preferably from 0.02 to 1%, of the copolymer according to the invention.
- the weight ratio of copolymer to pesticide can in this case be from 1:10 to 500:1, in particular from 1:4 to 4:1.
- Concentrate formulations which are diluted prior to use, may comprise the pesticide in amounts of from 5 to 60% by weight, preferably from 20 to 40%, and the copolymer based on acrylamidoalkylsulfonic acid salts in amounts of from 3 to 50% by weight.
- the weight ratio of copolymer to pesticide can be from 1:20 to 1:1, preferably from 1:10 to 1:2.
- the formulations according to the invention may comprise further thickeners, antigelling agents, antifreeze, solvents, dispersants, emulsifiers, preservatives, adjuvants, binders, antifoams, thinners and wetting agents.
- the thinner used can be xanthan gum and/or cellulose, for example carboxy-, methyl-, ethyl- or propylcellulose, in amounts of from 0.01 to 5% by weight, based on the finished composition.
- Suitable solvents are monopropylene glycol and animal and mineral oils.
- Suitable dispersants and emulsifiers are nonionic, amphoteric, cationic and anionic surfactants.
- Suitable for use as preservatives are organic acids and esters thereof, for example ascorbic acid, ascorbic acid palmitate, sorbate, benzoic acid, methyl- and propyl-4-hydroxybenzoate, propionate, phenol, for example 2-phenylphenate,
- Suitable antifoams are polysilicones.
- Adjuvants that are available are polyglycerol esters, alcohol ethoxylates, alkylpolysaccharides, fatty amine ethoxylates, sorbitan and sorbitol ethoxylate derivatives and derivatives of alk(en)ylsuccinic anhydride.
- Suitable diluents, absorbents or carriers are carbon black, talc, kaolin, aluminum stearate, calcium stearate or magnesium stearate, sodium tripolyphosphate, sodium tetraborate, sodium sulfate, silicates and sodium benzoate.
- the wetting agents used can be alcohol ethoxylates/propoxylates.
- Polymer 1 was prepared as follows:
- This reaction vessel was flashed with nitrogen gas, and in a gentle countercurrent of nitrogen, 245 g of acrylamido-2-methylpropanesulfonic acid AMPS 2404® (registered trade mark of Lubrizol) were introduced.
- the AMPS did not dissolve completely in the tert-butanol, and some of it was present as a solid-in-liquid dispersion.
- the pH of this mixture was below pH 1.
- gaseous ammonia was introduced above the liquid phase until the pH of the dispersion was between pH 7 and 8. After the desired pH range had been reached, stirring was continued for 1 hour, and the pH was monitored continuously.
- the reaction vessel was once more flashed with nitrogen, and 105 g of acrylamide were introduced.
- the pH was checked once more and, if required, adjusted to a range of pH 7-8.
- a constant stream of nitrogen was passed through the solution for at least 1 hour.
- the residual oxygen content was checked using an oxygen electrode. If the measured residual oxygen content in the liquid phase is above the value of 1 ppm, the liquid phase has to be inertized again, until this value is reached.
- 1.5 g of AIBN were added in a gentle stream of nitrogen, and the reaction vessel was heated to 60° C. Shortly after an internal temperature of 60° C. had been reached, introduction of nitrogen gas was terminated, the polymerization reaction typically starting after a few minutes, which could be detected by an increase in temperature of 10-15° C. Approximately 30 minutes after the polymerization reaction had started, the temperature maximum had been passed, and the temperature in the reaction vessel was increased to the boiling point of tert-butanol, using the heating bath.
- reaction product present as a viscous suspension of polymers in tert-butanol, was separated off by filtering off the tert-butanol, followed by dying in a vacuum drying cabinet.
- Dry matter 96% by weight (2.5% by weight of tert-butanol, 1.5% by weight of water)
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Abstract
Description
- The present invention relates to the use of water-soluble or water-swellable copolymers based on acrylamidoalkylsulfonic acid salts as drift control agents in crop protection compositions.
- Pesticides are applied in a highly efficient manner to agricultural production fields using spray tanks in airplanes, tractors and other devices. To achieve an application of the active substances which is as accurate as possible, it is necessary to obtain a spray cone which is as narrow as possible, and to avoid a drift of the spray mist from the target area.
- The drift of the spray cone is determined substantially by the droplet size. The smaller the droplets, the longer the residence time in the air and the higher the tendency to evaporate and/or to drift horizontally and to miss the target location. The drift effect can be reduced considerably by adding suitable drift control agents to pesticide formulations, which drift control agents increase the size of the droplets in the spray mist. The formulations modified by drift control agents additionally have to be insensitive to shear forces to which they are exposed in the spray pumps and nozzles. Drift control agents are furthermore required to have good biological degradability, compatibility with the other components of the crop protection composition and high storage and temperature stability. It is well known in the prior art that the rheological properties of aqueous compositions can be modified by adding water-soluble polymers, for example polyacrylamides, acrylamide/acrylic acid polymers, sodium polyacrylate, carboxymethylcellulose, hydroxyethylcellulose, methylcellulose, polysaccharides and natural and synthetic guar gum
- (U.S. Pat. No. 4,413,087, US 4,505,827, US 5,874,096).
- Unsatisfactory is the viscoelastic behavior of the additives when shear and pressure forces are applied.
- Under mechanical stress in the spraying device, the viscosity is lowered and the droplet size in the spray mist is reduced.
- It is a further disadvantage that the polymers used for modifying the viscosity of the aqueous preparations lose some of their thickening action in the presence of electrolytes, for example sodium chloride, calcium chloride and magnesium sulfate. Cellulose derivatives are highly electrolyte-tolerant but not temperature-stable enough. Biopolymers, such as xanthan gum, are electrolyte- and thermostable, but expensive and poorly storage-stable.
- Both for economical and ecological reasons, there are attempts to find suitable drift control agents which effectively increase the droplet volumes of the aqueous compositions, even under the influence of shear forces, in the presence of electrolytes and under thermal stress, and which reduce the drift of the spray cone.
- Polymers of acrylamido-2-methyl-propanesulfonic acid and acrylamide and their use as additives in cement slurries for cementing deep underground drillings are known from DE 197 52 093.
- Surprisingly, it has been found that water-soluble and water-swellable copolymers based on acrylamidoalkylsulfonates and olefinically unsaturated monomers containing at least one oxygen, nitrogen, sulfur or phosphorus atom and from 0 to 20% by weight of a suitable crosslinker are very good thickeners for aqueous preparations and, when these compositions are sprayed, effect an increase in the particle size and a reduction of the spray cone. In addition, the polymers used according to the invention have good viscosity properties. Under the action of shear forces, the particle volumes are reduced only slightly. In addition, the compositions according to the invention have high electrolyte, temperature and storage stability.
-
- in which R1 is hydrogen or methyl, Z is a C1-C4-alkylene group and X is hydrogen, an alkali metal or ammonium, from 10 to 99% by weight of a repetitive structural unit which is derived from olefinically unsaturated comonomers containing at least one oxygen, nitrogen, sulfur or phosphorus atom and from 0 to 20% by weight of crosslinking structures originating from monomers having at least two olefinic double bonds.
-
-
- where R5=hydrogen or methyl, R6 and R7 independently of one another are hydrogen or C2-C22-alkyl.
- The preferred monomer of the formula (1) is 2-acrylamido-2-methylpropanesulfonic acid and its salts, preferably the ammonium salt. Suitable olefinically unsaturated monomers containing at least one oxygen, nitrogen, sulfur or phosphorus atom are, for example, styrenesulfonic acid, acrylamidopropylmethylenesulfonic acid (AMPS), vinylsulfonic acid, vinylphosphonic acid, allylsulfonic acid, methallylsulfonic acid, acrylic acid, methacrylic acid and maleic acid (and its anhydride) and the salts of the acids mentioned above with mono- and divalent counterions. Preferred counterions are lithium, sodium, potassium, magnesium, calcium, ammonium, monoalkylammonium, dialkylammonium, trialkylammonium or tetraalkylammonium, where the alkyl substituents of the amines independently of one another are C1-C22-alkyl radicals which may be substituted by 0 to 3 hydroxyalkyl groups, the alkyl chain length of which may vary in a range from C2-C10. Additionally, it is also possible to use mono- to triethoxylated ammonium compounds with a different degree of ethoxylation. Particularly preferred counterions are sodium and ammonium. The degree of neutralization of the mole fraction of the acids described above may also differ from 100%. Suitable are all degrees of neutralization between 0 and 100%, the range between 70 and 100% being particularly preferred.
- Furthermore suitable are esters of acrylic or methacrylic acid with aliphatic, aromatic or cycloaliphatic alcohols having a carbon number of C1-C22, open-chain or cyclic.
- N-vinylamides (vinyllactams) of a ring size of from 3 to 9, for example N-vinylformamide (VIFA), N-vinylmethylformamide, N-vinylmethylacetamide (VIMA), N-vinylacetamide, N-vinylpyrrolidone (NVP) and N-vinylcaprolactam. Amides of acrylic or methacrylic acid can also be used as monomers. Examples which may be mentioned are, inter alia, acrylamide, N,N-dimethylacrylamide, N,N-diethylacrylamide, methacrylamide, alkoxylated acrylamides or methacrylamides (for example MAPTAC, APTAC). Other suitable monomers are 2- and 4-vinylpyridine, vinyl acetate, glycidyl methacrylate, acrylonitrile, vinylphosphonic acid and esters or alkali metal, alkaline earth metal or ammonium salts thereof, DADMAC and vinylsulphonic acid or its corresponding Na+, K+, Li+, Mg2+ or Ca2+ salts. It is, of course, also possible for combinations of the monomers listed to be present. As already mentioned, the sum of the comonomers used can be from 9.99 to 98.99% of the total mass of the polymer. The polymers used according to the invention as drift control agents in crop protection compositions can be crosslinked, i.e. they contain compounds having at least two double bonds which are polymerized into the polymer. Suitable crosslinkers are, in particular, methylenebisacrylamide or methylenebismethacrylamide, esters of unsaturated mono- or polycarboxylic acids of polyols, such as diacrylate or triacrylate or methacrylates, for example butanediol or ethylene glycol diacrylate or methacrylate, and also trimethylolpropane tri(meth)acrylate and allyl compounds, such as allyl (meth)acrylate, triallyl cyanurate, diallyl maleate, polyallyl esters, tetraallyloxyethane, triallylamine, tetraallylethylenediamine, allyl esters of phosphoric acid and derivatives of vinylphosphonic acid, furthermore, allyl or vinyl ethers, for example dipropylene glycol diallyl ether, polyglycol diallyl ether, triethylene glycol divinyl ether, hydroquinone diallyl ether, multifunctional alcohols, tetraethylene glycol diacrylate, trimethylolpropane diallyl ether, methylene-bis-acrylamide or divinylbenzene.
- The polymers according to the invention are prepared by free-radical copolymerization in C1-C6-alcohols, preferably in tert-butanol.
- The polymerization can be carried out at in a temperature range of from 0 to 150° C., preferably between 10 and 100° C., and at atmospheric pressure or else under elevated or reduced pressure. As usual, the polymerization can also be carried out in an atmosphere of protective gas, preferably under nitrogen.
- For initiating the polymerization, it is possible to use high-energy fields or the customary chemical polymerization initiators, for example organic or inorganic peroxides, such as benzoyl peroxide, tert-butyl hydroperoxide, methylene ketone peroxide, cumene hydroperoxide, azo compounds, such as, for example, azodiisobutyronitrile, and also inorganic peroxy compounds, such as (NH4)2S2O8 or K2S2O8 or H2O2, if appropriate in combination with reducing agents, such as sodium hydrogen sulfite and iron(II) sulfate or redox systems which, as reducing component, comprise an aliphatic or aromatic sulfonic acid, such as benzenesulfonic acid and toluenesulfonic acid, or derivatives of these acids, such as, for example, Mannich adducts of sulfinic acid, aldehydes and amino compounds.
- In general, the polymers have a number-average molecular weight of from 1000 to 20 000 000 g/mol. Preference is given to a molecular weight of from 20 000 to 5 000 000, in particular 100 000 to 1 500 000 g/mol.
- The invention provides furthermore pesticide preparations comprising a copolymer of repetitive structural units of the formula (1), of structural units which are derived from olefinically unsaturated compounds containing an oxygen, nitrogen, sulfur or phosphorus atom and crosslinking structures as described above. These pesticide preparations may also comprise copolymers of the monomers of the formulae (2) and (3). In addition to these copolymers serving as drift control agents, the pesticide preparations comprise the customary active compounds, such as herbicides, insecticides, fungicides, acaricides, bactericides, molluscides, nematicides or rodenticides. Preference is given to herbicidal preparations. Suitable herbicidally active compounds are in particular glyphosate, but also acifluorfen, asulam, benazolin, bentazone, bilanafos, bromacil, bromoxynil, chloramben, clopyralid, 2,4-D, 2,4-DB, dalapon, dicamba, dichlorprop, diclofop, endothall, fenach, fenoxaprop, glamprop, fluazifop, flumiclorac, fluoroglacofen, fomesafen, fosamine, glufosinate, haloxyfop, imazapic, imazamethabenz, imazamox, imazapyr, imazaquin, imazethapyr, ioxynil, MCPA, MCPB, mecoprop, methylarsonic acid/MSMA, naptalam, picloram, quinclorac, quizalofop, 2,3,6-TBS-TCA.
- The preparations according to the invention may comprise the copolymers based on acrylamidoalkylsulfonic acid salts as drift control agents in virtually any amount. Preference is given to the following preparations:
- Formulations as tank-mix and ready-to-use compositions comprise from 0.01 to 10% by weight, preferably from 0.0025 to 2% by weight, of pesticide and from 0.0001% by weight to 5% by weight, preferably from 0.0025 to 2%, particularly preferably from 0.02 to 1%, of the copolymer according to the invention. The weight ratio of copolymer to pesticide can in this case be from 1:10 to 500:1, in particular from 1:4 to 4:1.
- Concentrate formulations, which are diluted prior to use, may comprise the pesticide in amounts of from 5 to 60% by weight, preferably from 20 to 40%, and the copolymer based on acrylamidoalkylsulfonic acid salts in amounts of from 3 to 50% by weight. Here, the weight ratio of copolymer to pesticide can be from 1:20 to 1:1, preferably from 1:10 to 1:2.
- In addition to the copolymers based on acrylamidoalkylsulfonic acid salts, the formulations according to the invention may comprise further thickeners, antigelling agents, antifreeze, solvents, dispersants, emulsifiers, preservatives, adjuvants, binders, antifoams, thinners and wetting agents.
- The thinner used can be xanthan gum and/or cellulose, for example carboxy-, methyl-, ethyl- or propylcellulose, in amounts of from 0.01 to 5% by weight, based on the finished composition. Suitable solvents are monopropylene glycol and animal and mineral oils. Suitable dispersants and emulsifiers are nonionic, amphoteric, cationic and anionic surfactants.
- Suitable for use as preservatives are organic acids and esters thereof, for example ascorbic acid, ascorbic acid palmitate, sorbate, benzoic acid, methyl- and propyl-4-hydroxybenzoate, propionate, phenol, for example 2-phenylphenate,
- 1,2-benzisothiazolin-3-one, formaldehyde, sulfurous acid and salts thereof. Suitable antifoams are polysilicones. Adjuvants that are available are polyglycerol esters, alcohol ethoxylates, alkylpolysaccharides, fatty amine ethoxylates, sorbitan and sorbitol ethoxylate derivatives and derivatives of alk(en)ylsuccinic anhydride. Suitable diluents, absorbents or carriers are carbon black, talc, kaolin, aluminum stearate, calcium stearate or magnesium stearate, sodium tripolyphosphate, sodium tetraborate, sodium sulfate, silicates and sodium benzoate.
- The wetting agents used can be alcohol ethoxylates/propoxylates.
- To assess the effect of the copolymers used according to the invention, from the sodium salt of 2-acrylicamido-2-methylsulfonate and acrylamide, on the drift potential of an aqueous formulation, the mean droplet volumes of the spray mist and the distribution of the droplet size were determined both under normal conditions and under the action of shear forces and compared with the values determined for pure water.
TABLE 1 Mean diameter (μm) of the droplets Diameter (μm) Without shear With shear Substance forces forces Water 262 260 Emigen DPR 476.1 296.3 Polymer 1 510 420 - At a temperature of 20° C., an aqueous solution of 0.12 g/l of polymer 2000 or 12.00 g/l of Emigen DPR/I was sprayed using a Teejet XR8003 VS spray nozzle (tip@ 40 psi) from a distance of 30 cm on to an Aerometrics PDPA laser measuring system (325 volts), and the particle diameter of 10 000 droplets was determined. In each case, the measurement was carried out in three repetitions. Using a rotary pump at a rotation speed of 4.0 gal/min and a total of 12 rotations, the aqueous solutions were, at a temperature of 20° C., subjected to shear forces, and the droplet diameters were determined.
TABLE 2 Percentage of droplets < 150 μm, in % by volume % by volume Without shear With shear Substance forces forces Water 19.0 19.0 Emigen DPR 6.6 16.6 Polymer 1 7.0 9.5 - Polymer 1 was prepared as follows:
- Copolymer of 70% by weight of AMPS and 30% by weight of AM, ammonium salt
- 1700 g of rectified tert-butanol were initially charged in a 3 liter Quickfit flask fitted with anchor stirrer, reflux condenser with waste-gas washer, combined thermometer/pH-meter and gas inlet tube, and admixed with 50 ml of distilled water. The reaction vessel was located in a thermostatted heating bath.
- This reaction vessel was flashed with nitrogen gas, and in a gentle countercurrent of nitrogen, 245 g of acrylamido-2-methylpropanesulfonic acid AMPS 2404® (registered trade mark of Lubrizol) were introduced. The AMPS did not dissolve completely in the tert-butanol, and some of it was present as a solid-in-liquid dispersion. The pH of this mixture was below pH 1. Using the gas inlet tube, gaseous ammonia was introduced above the liquid phase until the pH of the dispersion was between pH 7 and 8. After the desired pH range had been reached, stirring was continued for 1 hour, and the pH was monitored continuously. The reaction vessel was once more flashed with nitrogen, and 105 g of acrylamide were introduced. After the acrylamide had been introduced, the pH was checked once more and, if required, adjusted to a range of pH 7-8. A constant stream of nitrogen was passed through the solution for at least 1 hour. After this inertization time, the residual oxygen content was checked using an oxygen electrode. If the measured residual oxygen content in the liquid phase is above the value of 1 ppm, the liquid phase has to be inertized again, until this value is reached. Subsequently 1.5 g of AIBN were added in a gentle stream of nitrogen, and the reaction vessel was heated to 60° C. Shortly after an internal temperature of 60° C. had been reached, introduction of nitrogen gas was terminated, the polymerization reaction typically starting after a few minutes, which could be detected by an increase in temperature of 10-15° C. Approximately 30 minutes after the polymerization reaction had started, the temperature maximum had been passed, and the temperature in the reaction vessel was increased to the boiling point of tert-butanol, using the heating bath.
- Under gentle reflux, the material, which was now viscous, was stirred for another two hours.
- The reaction product, present as a viscous suspension of polymers in tert-butanol, was separated off by filtering off the tert-butanol, followed by dying in a vacuum drying cabinet.
- Yield: 365 g of polymer 1
- Ammonium salt of poly (acrylamido-2-methylpropanesulfonic acid-co-acrylamide)
- Dry matter: 96% by weight (2.5% by weight of tert-butanol, 1.5% by weight of water)
- k-value of a 0.5% by weight strength solution: 212
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
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US20050085391A1 (en) * | 2001-12-22 | 2005-04-21 | Meyer Gerd R. | Aqueous plant-protection formulations |
US20060142159A1 (en) * | 2001-12-22 | 2006-06-29 | Meyer Gerd R | Plant-protective agents in the form of suspensions |
WO2011128236A2 (en) | 2010-04-14 | 2011-10-20 | Lamberti Spa | Process for preparing diluted agrochemical spray formulations with improved drift control |
WO2014040120A1 (en) * | 2012-09-11 | 2014-03-20 | Vitel Australia Pty Ltd | Effervescent tablet for spray drift reduction and method of use |
DE102014211826A1 (en) | 2014-06-20 | 2015-12-24 | Evonik Degussa Gmbh | Use of defoamers as anti-drift additives |
Families Citing this family (18)
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DE10206468A1 (en) * | 2002-02-16 | 2003-08-28 | Clariant Gmbh | Pesticides |
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- 2000-02-16 DE DE10007044A patent/DE10007044A1/en not_active Withdrawn
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2001
- 2001-02-03 DK DK01911587T patent/DK1278787T3/en active
- 2001-02-03 AT AT01911587T patent/ATE357849T1/en not_active IP Right Cessation
- 2001-02-03 KR KR1020027010565A patent/KR20020075423A/en not_active Withdrawn
- 2001-02-03 CA CA002400424A patent/CA2400424A1/en not_active Abandoned
- 2001-02-03 WO PCT/EP2001/001170 patent/WO2001060877A1/en active IP Right Grant
- 2001-02-03 JP JP2001560258A patent/JP2003523421A/en not_active Withdrawn
- 2001-02-03 IL IL15121501A patent/IL151215A0/en unknown
- 2001-02-03 CN CN01805860A patent/CN1406256A/en active Pending
- 2001-02-03 DE DE50112269T patent/DE50112269D1/en not_active Expired - Lifetime
- 2001-02-03 BR BRPI0108410-0A patent/BR0108410B1/en not_active IP Right Cessation
- 2001-02-03 ES ES01911587T patent/ES2283395T3/en not_active Expired - Lifetime
- 2001-02-03 EP EP01911587A patent/EP1278787B1/en not_active Expired - Lifetime
- 2001-02-03 MX MXPA02007986A patent/MXPA02007986A/en active IP Right Grant
- 2001-02-15 US US09/784,536 patent/US6391962B2/en not_active Expired - Lifetime
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US20050085391A1 (en) * | 2001-12-22 | 2005-04-21 | Meyer Gerd R. | Aqueous plant-protection formulations |
US20060142159A1 (en) * | 2001-12-22 | 2006-06-29 | Meyer Gerd R | Plant-protective agents in the form of suspensions |
WO2011128236A2 (en) | 2010-04-14 | 2011-10-20 | Lamberti Spa | Process for preparing diluted agrochemical spray formulations with improved drift control |
WO2014040120A1 (en) * | 2012-09-11 | 2014-03-20 | Vitel Australia Pty Ltd | Effervescent tablet for spray drift reduction and method of use |
DE102014211826A1 (en) | 2014-06-20 | 2015-12-24 | Evonik Degussa Gmbh | Use of defoamers as anti-drift additives |
Also Published As
Publication number | Publication date |
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CA2400424A1 (en) | 2001-08-23 |
EP1278787B1 (en) | 2007-03-28 |
KR20020075423A (en) | 2002-10-04 |
DK1278787T3 (en) | 2007-08-06 |
DE10007044A1 (en) | 2001-08-23 |
US6391962B2 (en) | 2002-05-21 |
BR0108410B1 (en) | 2011-01-25 |
ATE357849T1 (en) | 2007-04-15 |
MXPA02007986A (en) | 2002-11-29 |
IL151215A0 (en) | 2003-04-10 |
EP1278787A1 (en) | 2003-01-29 |
WO2001060877A1 (en) | 2001-08-23 |
JP2003523421A (en) | 2003-08-05 |
ES2283395T3 (en) | 2007-11-01 |
DE50112269D1 (en) | 2007-05-10 |
CN1406256A (en) | 2003-03-26 |
BR0108410A (en) | 2003-03-11 |
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