WO1999055645A1 - Agricultural adjuvant - Google Patents
Agricultural adjuvant Download PDFInfo
- Publication number
- WO1999055645A1 WO1999055645A1 PCT/US1999/006553 US9906553W WO9955645A1 WO 1999055645 A1 WO1999055645 A1 WO 1999055645A1 US 9906553 W US9906553 W US 9906553W WO 9955645 A1 WO9955645 A1 WO 9955645A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- weight
- surfactant
- component
- nonionic surfactant
- Prior art date
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- 239000002671 adjuvant Substances 0.000 title claims abstract description 30
- 239000000203 mixture Substances 0.000 claims abstract description 175
- 239000002736 nonionic surfactant Substances 0.000 claims abstract description 34
- 239000003337 fertilizer Substances 0.000 claims abstract description 18
- 239000003945 anionic surfactant Substances 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- -1 fatty acid ester Chemical class 0.000 claims description 55
- 125000004432 carbon atom Chemical group C* 0.000 claims description 47
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 45
- 229930195729 fatty acid Natural products 0.000 claims description 45
- 239000000194 fatty acid Substances 0.000 claims description 45
- 239000004094 surface-active agent Substances 0.000 claims description 40
- 235000000346 sugar Nutrition 0.000 claims description 33
- 150000004665 fatty acids Chemical class 0.000 claims description 28
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 24
- 150000002191 fatty alcohols Chemical class 0.000 claims description 19
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 18
- 150000002193 fatty amides Chemical class 0.000 claims description 18
- 150000002195 fatty ethers Chemical class 0.000 claims description 18
- 239000003921 oil Substances 0.000 claims description 18
- 235000019198 oils Nutrition 0.000 claims description 18
- 125000005456 glyceride group Chemical group 0.000 claims description 15
- 239000004359 castor oil Substances 0.000 claims description 14
- 235000019438 castor oil Nutrition 0.000 claims description 14
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 14
- 239000000758 substrate Substances 0.000 claims description 14
- 229910019142 PO4 Inorganic materials 0.000 claims description 12
- 239000010452 phosphate Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000002480 mineral oil Substances 0.000 claims description 11
- 239000000618 nitrogen fertilizer Substances 0.000 claims description 11
- 229920000847 nonoxynol Polymers 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000003208 petroleum Substances 0.000 claims description 10
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 7
- 150000004702 methyl esters Chemical class 0.000 claims description 7
- 125000004494 ethyl ester group Chemical group 0.000 claims description 6
- 239000002280 amphoteric surfactant Substances 0.000 claims description 5
- 239000003093 cationic surfactant Substances 0.000 claims description 5
- IEORSVTYLWZQJQ-UHFFFAOYSA-N 2-(2-nonylphenoxy)ethanol Chemical group CCCCCCCCCC1=CC=CC=C1OCCO IEORSVTYLWZQJQ-UHFFFAOYSA-N 0.000 claims description 4
- CSGLCWIAEFNDIL-UHFFFAOYSA-O azanium;urea;nitrate Chemical group [NH4+].NC(N)=O.[O-][N+]([O-])=O CSGLCWIAEFNDIL-UHFFFAOYSA-O 0.000 claims description 4
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 claims description 4
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 claims description 4
- 229940073769 methyl oleate Drugs 0.000 claims description 4
- 125000000837 carbohydrate group Chemical group 0.000 claims 3
- 235000010446 mineral oil Nutrition 0.000 claims 3
- 239000004064 cosurfactant Substances 0.000 description 19
- 238000006116 polymerization reaction Methods 0.000 description 15
- 239000004009 herbicide Substances 0.000 description 13
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 150000001720 carbohydrates Chemical group 0.000 description 8
- 239000000417 fungicide Substances 0.000 description 7
- 150000003014 phosphoric acid esters Chemical class 0.000 description 7
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- 150000004996 alkyl benzenes Chemical class 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 229940077388 benzenesulfonate Drugs 0.000 description 4
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 4
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- LINPVWIEWJTEEJ-UHFFFAOYSA-N methyl 2-chloro-9-hydroxyfluorene-9-carboxylate Chemical compound C1=C(Cl)C=C2C(C(=O)OC)(O)C3=CC=CC=C3C2=C1 LINPVWIEWJTEEJ-UHFFFAOYSA-N 0.000 description 4
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 4
- 239000005648 plant growth regulator Substances 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 239000003760 tallow Substances 0.000 description 4
- WOMTYMDHLQTCHY-UHFFFAOYSA-N 3-methylamino-1,2-propanediol Chemical compound CNCC(O)CO WOMTYMDHLQTCHY-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 244000060011 Cocos nucifera Species 0.000 description 3
- 235000013162 Cocos nucifera Nutrition 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 150000008051 alkyl sulfates Chemical class 0.000 description 3
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229930182830 galactose Natural products 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229960004063 propylene glycol Drugs 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- JCZPMGDSEAFWDY-SQOUGZDYSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanamide Chemical compound NC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO JCZPMGDSEAFWDY-SQOUGZDYSA-N 0.000 description 2
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 2
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 2
- XLGVHAQDCFITCH-UHFFFAOYSA-N 2,3-dihydroxypropanamide Chemical compound NC(=O)C(O)CO XLGVHAQDCFITCH-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- YOOPHLDCWPOWDX-QCICJENWSA-N beta-D-GlcpA-(1->6)-beta-D-Galp Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)O[C@@H]1CO[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](C(O)=O)O1 YOOPHLDCWPOWDX-QCICJENWSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 2
- 229940088623 biologically active substance Drugs 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical compound C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 150000002016 disaccharides Chemical class 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- HSEMFIZWXHQJAE-UHFFFAOYSA-N hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(N)=O HSEMFIZWXHQJAE-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 2
- 229940116335 lauramide Drugs 0.000 description 2
- 125000001483 monosaccharide substituent group Chemical group 0.000 description 2
- 150000002772 monosaccharides Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 229940087291 tridecyl alcohol Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LCDOBQBPGARYNY-VFRRUGBOSA-N (2R,3R)-N-decan-2-yl-2,3,4-trihydroxybutanamide Chemical compound CCCCCCCCC(C)NC(=O)[C@H](O)[C@H](O)CO LCDOBQBPGARYNY-VFRRUGBOSA-N 0.000 description 1
- RRBHVVXZCRBUSA-GHMZBOCLSA-N (2r,3r)-2,3,4-trihydroxy-n-octylbutanamide Chemical compound CCCCCCCCNC(=O)[C@H](O)[C@H](O)CO RRBHVVXZCRBUSA-GHMZBOCLSA-N 0.000 description 1
- MDSNRZIKSHAKQJ-IAGOWNOFSA-N (2r,3r)-2,3,4-trihydroxy-n-tetradecylbutanamide Chemical compound CCCCCCCCCCCCCCNC(=O)[C@H](O)[C@H](O)CO MDSNRZIKSHAKQJ-IAGOWNOFSA-N 0.000 description 1
- NHZGTVBIVDEEFL-HUUCEWRRSA-N (2r,3r)-n-dodecyl-2,3,4-trihydroxybutanamide Chemical compound CCCCCCCCCCCCNC(=O)[C@H](O)[C@H](O)CO NHZGTVBIVDEEFL-HUUCEWRRSA-N 0.000 description 1
- CXNPLSGKWMLZPZ-GIFSMMMISA-N (2r,3r,6s)-3-[[(3s)-3-amino-5-[carbamimidoyl(methyl)amino]pentanoyl]amino]-6-(4-amino-2-oxopyrimidin-1-yl)-3,6-dihydro-2h-pyran-2-carboxylic acid Chemical compound O1[C@@H](C(O)=O)[C@H](NC(=O)C[C@@H](N)CCN(C)C(N)=N)C=C[C@H]1N1C(=O)N=C(N)C=C1 CXNPLSGKWMLZPZ-GIFSMMMISA-N 0.000 description 1
- CSLZWNYEHKZPEL-HZSPNIEDSA-N (2r,3s,4r)-n-decyl-2,3,4,5-tetrahydroxypentanamide Chemical compound CCCCCCCCCCNC(=O)[C@H](O)[C@@H](O)[C@H](O)CO CSLZWNYEHKZPEL-HZSPNIEDSA-N 0.000 description 1
- GQSHHCDEBSCCRR-OWCLPIDISA-N (2r,3s,4r)-n-dodecyl-2,3,4,5-tetrahydroxypentanamide Chemical compound CCCCCCCCCCCCNC(=O)[C@H](O)[C@@H](O)[C@H](O)CO GQSHHCDEBSCCRR-OWCLPIDISA-N 0.000 description 1
- 229940116368 1,2-benzisothiazoline-3-one Drugs 0.000 description 1
- TUBQDCKAWGHZPF-UHFFFAOYSA-N 1,3-benzothiazol-2-ylsulfanylmethyl thiocyanate Chemical compound C1=CC=C2SC(SCSC#N)=NC2=C1 TUBQDCKAWGHZPF-UHFFFAOYSA-N 0.000 description 1
- CJUUXVFWKYRHAR-UHFFFAOYSA-M 1-Naphthaleneacetic acid sodium salt Chemical compound [Na+].C1=CC=C2C(CC(=O)[O-])=CC=CC2=C1 CJUUXVFWKYRHAR-UHFFFAOYSA-M 0.000 description 1
- SVPKNMBRVBMTLB-UHFFFAOYSA-N 2,3-dichloronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=C1 SVPKNMBRVBMTLB-UHFFFAOYSA-N 0.000 description 1
- YTQQIHUQLOZOJI-UHFFFAOYSA-N 2,3-dihydro-1,2-thiazole Chemical compound C1NSC=C1 YTQQIHUQLOZOJI-UHFFFAOYSA-N 0.000 description 1
- ZIWPNENWXIHHRV-UHFFFAOYSA-N 2,3-dihydroxy-n-octylpropanamide Chemical compound CCCCCCCCNC(=O)C(O)CO ZIWPNENWXIHHRV-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 1
- FOZDDTHPIZJCPA-UHFFFAOYSA-N 2-(2,6-diethylphenyl)-5-methylisoindole-1,3-dione Chemical compound CCC1=CC=CC(CC)=C1N1C(=O)C2=CC(C)=CC=C2C1=O FOZDDTHPIZJCPA-UHFFFAOYSA-N 0.000 description 1
- PNTSMIMYOILILJ-UHFFFAOYSA-N 2-(2-chloro-4-methylphenoxy)acetic acid Chemical compound CC1=CC=C(OCC(O)=O)C(Cl)=C1 PNTSMIMYOILILJ-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
- NMWKWBPNKPGATC-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2-benzofuran-1(3H)-one Chemical compound ClC1=C(Cl)C(Cl)=C2COC(=O)C2=C1Cl NMWKWBPNKPGATC-UHFFFAOYSA-N 0.000 description 1
- AKKPXGYDZXXJLI-UHFFFAOYSA-N 4-(3,5-dichloroanilino)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)NC1=CC(Cl)=CC(Cl)=C1 AKKPXGYDZXXJLI-UHFFFAOYSA-N 0.000 description 1
- QCPASDYEQAVIJF-UHFFFAOYSA-N 4-chloro-3-methyl-1,3-benzothiazol-2-one Chemical compound C1=CC=C2SC(=O)N(C)C2=C1Cl QCPASDYEQAVIJF-UHFFFAOYSA-N 0.000 description 1
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- 238000006722 reduction reaction Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05C—NITROGENOUS FERTILISERS
- C05C1/00—Ammonium nitrate fertilisers
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
- C05G3/00—Mixtures of one or more fertilisers with additives not having a specially fertilising activity
- C05G3/50—Surfactants; Emulsifiers
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
- C05G5/00—Fertilisers characterised by their form
- C05G5/20—Liquid fertilisers
Definitions
- the present invention generally relates to adjuvants used to formulate agricultural compositions. More particularly, the invention relates to a novel adjuvant composition which, when used in combination with a biologically active ingredient, significantly potentiates the performance of the product.
- various agricultural materials such as insecticides, insect repellents, fungicides, bactericides, herbicides, and plant growth regulators may be formulated into various products for use on crops and ornamental plants, for controlling weeds, insects and the like. These products may be applied in the form of a liquid or a semi-solid dispersion. Regardless of the method of application, it is advantageous to include within the product an adjuvant in order to enhance the effectiveness and performance of the agricultural product's active ingredient, thereby requiring less actives to be used to perform a certain function.
- an oil component selected from the group consisting of a fatty acid 2 ester, a seed oil, a petroleum oil, a fatty acid, a fatty alcohol, a fatty ether, an fatty amide, a glyceride and mixtures thereof;
- a nonionic surfactant selected from the group consisting of sugar surfactants, alkoxylated fatty alcohols, alkoxylated fatty acids, alkoxylated fatty ethers, alkoxylated fatty amides, ethoxylated seed oils, ethoxylated mineral oils, nonylphenol ethoxylates, alkoxylated alkyl phenols, ethoxylated glycerides, castor oil ethoxylates and mixtures thereof;
- the present invention is also directed to an agricultural composition containing:
- an oil component selected from the group consisting of a fatty acid ester, a seed oil, a petroleum oil, a fatty acid, a fatty alcohol, a fatty ether, a fatty amide, a glyceride and mixtures thereof;
- a nonionic surfactant selected from the group consisting of sugar surfactants, alkoxylated fatty alcohols, alkoxylated fatty acids, alkoxylated fatty ethers, alkoxylated fatty amides, ethoxylated seed oils, ethoxylated mineral oils, nonylphenol ethoxylates, alkoxylated alkyl phenols, ethoxylated glycerides, castor oil ethoxylates and mixtures thereof;
- the present invention is also directed to a process for treating an agricultural substrate involving contacting the substrate with the above- disclosed agricultural composition.
- the term "agricultural substrate”, as used herein, means a plant.
- the adjuvant composition of the present invention is a combination of at least three adjuvant components, namely, an oil component, certain nonionic surfactants, an anionic component and a fertilizer component.
- Suitable oil components include those selected from the group consisting of a fatty acid ester, a seed oil, a petroleum oil, a fatty acid, a fatty alcohol, a fatty ether, a fatty amide, a glyceride and mixtures thereof.
- Fatty acid esters which may be used are those having the general formula:
- R 2 COOC n H 2n+1 wherein R 2 is an alkyl radical having from about 4 to about 22 carbon atoms, and n is a number from 1-4. They are derived by the esterification of a fatty acid with an alkanol.
- Preferred fatty acid esters are methyl and ethyl esters derived from the esterification of unsaturated fatty acids having from about 18 to about 22 carbon atoms. Particularly preferred methyl esters include methyl oleate, methyl laurate and methyl soyate.
- Preferred ethyl esters include ethyl oleate and ethyl canolate.
- Suitable fatty acids from which the fatty acid esters may be derived include, but are not limited to, coconut and other vegetable oils, tallow, etc.
- Alkoxylated fatty acid esters may also be employed. These include fatty acid esters such as those listed above which are alkoxylated with ethylene oxide, propylene oxide and combinations thereof.
- Fatty alcohols which may be employed in the present invention are saturated or unsaturated, branched or linear C 8 -C 20 alcohols.
- High molecular weight alcohols may be produced synthetically by the Oxo and Ziegler processes. Those having from 8 to 11 carbon atoms are generally oily liquids. On the other hand, those having greater than 11 carbon atoms are generally solids.
- Other methods of production are (1) reduction of vegetable seed oils and their fatty acids with sodium, (2) catalytic hydrogenation at 4 elevated temperatures and pressures, and (3) hydrolysis of spermaceti and sperm oil by saponification and vacuum fractional distillation.
- the more important commercial saturated alcohols are octyl, decyl, lauryl, myristyl, cetyl and stearyl.
- the commercially important unsaturated alcohols include oleyl, linoleyl and linolenyl. Guerbet alcohol ethoxylates may also be employed as a carrier component.
- the fatty acids which may be employed in the present invention are those composed of a chain of alkyl groups containing from 4 to 22 carbon atoms and characterized by a terminal carboxyl group.
- the fatty acids may be saturated such as, for example, butyric, lauric, palmitic and stearic or unsaturated such as, for example, oleic, linoleic and linolenic.
- the fatty ethers which may be employed are those generally derived from fatty alcohols, such as those listed above, by the elimination of water. They are generally characterized by the formula ROR wherein R is an alkyl group containing from 4 to 22 carbon atoms.
- Suitable seed oils are those derived from seeds and nuts and include, but are not limited to, castor, coconut, soybean, and the like. Preferred seed oils include soybean oil.
- Useful petroleum oils include, but are not limited to, petroleum and petroleum-derived oils.
- Preferred petroleum oils include mineral oils.
- Suitable glycerides include those derived from glycerol and a C ⁇ fatty acid. Preferred glycerides include glycerol mono/di oleate.
- Suitable nonionic surfactants for use in the present invention include sugar surfactants, alkoxylated fatty alcohols, alkoxylated fatty acids, alkoxylated fatty ethers, alkoxylated fatty amides, ethoxylated seed oils, ethoxylated mineral oils, nonylphenol ethoxylates, alkoxylated alkyl phenols, ethoxylated glycerides, castor oil ethoxylates, and mixtures thereof.
- Suitable sugar surfactants include those selected from the group consisting of an alkyl polyglycoside, an alkyl glucose ester, an aldobionamide, 5 a gluconamide, a glyceramide, a glyceroglycolipid, a polyhydroxy fatty acid amide and mixtures thereof.
- the alkyl polyglycosides which may be employed in the present invention are those corresponding to the formula: R 1 0(Z) a wherein R t is a monovalent organic radical having from about 6 to about 30 carbon atoms; Z is saccharide residue having 5 or 6 carbon atoms; a is a number having a value from 1 to about 6.
- the alkyl polyglucosides which can be used in the compositions and processes according to the invention are commercially available, for example, as APG® surfactants, GLUCOPON® surfactants, AGRIMUL® surfactants, or PLANTAREN® surfactants from Henkel Corporation, Ambler, PA, 19002. Examples of such surfactants include but are not limited to:
- AGRIMUL® PG 2067 Surfactant - an alkylpolyglycoside in which the alkyl group contains 8 to 10 carbon atoms and having an average degree of polymerization of 1.7.
- AGRIMUL® 2072 Surfactant - an alkyl polyglycoside in which the alkyl group contains 8 to 16 carbon atoms and having an average degree of polymerization of 1.6.
- AGRIMUL® 2065 Surfactant - an alkyl polyglycoside in which the alkyl group contains 12 to 16 carbon atoms and having an average degree of polymerization of 1.6.
- AGRIMUL® PG 2069 Surfactant - an alkyl polyglycoside in which the alkyl group contains 9 to 11 carbon atoms and having an average degree of polymerization of 1.6.
- AGRIMUL® 2062 Surfactant - an alkyl polyglycoside in which the alkyl group contains 12 to 16 carbon atoms and having an average degree of polymerization of 1.4.
- PLANTAREN® 2000 Surfactant - a C 8-16 alkyl polyglycoside in which the 6 alkyl group contains 8 to 16 carbon atoms and having an average degree of polymerization of 1.4.
- PLANTAREN® 1300 Surfactant - a C 12 . 16 alkyl polyglycoside in which the alkyl group contains 12 to 16 carbon atoms and having an average degree of polymerization of 1.6.
- alkyl polyglycoside surfactant compositions which are comprised of mixtures of compounds of formula I wherein Z represents a moiety derived from a reducing saccharide containing 5 or 6 carbon atoms; a is zero; and R 1 is an alkyl radical having from 8 to 20 carbon atoms.
- the composition is characterized in that it has increased surfactant properties and an HLB in the range of about 10 to about 16 and a non-Flory distribution of glycosides, which is comprised of a mixture of an alkyl monoglycoside and a mixture of alkyl polyglycosides having varying degrees of polymerization of 2 and higher in progressively decreasing amounts, in which the amount by weight of polyglycoside having a degree of polymerization of 2, or mixtures thereof with the polyglycoside having a degree of polymerization of 3, predominate in relation to the amount of monoglycoside, said composition having an average degree of polymerization of about 1.8 to about 3.
- compositions also known as peaked alkyl polyglucosides, can be prepared by separation of the monoglycoside from the original reaction mixture of alkyl monoglycoside and alkyl polyglycosides after removal of the alcohol. This separation may be carried out by molecular distillation and normally results in the removal of about 70-95% by weight of the alkyl monoglycosides.
- Preferred alkyl polyglycosides are those in which the alkyl group 7 contains from 8 to 12 carbon atoms and having an average degree of polymerization of 1.6 to 1.7.
- the most preferred alkyl polyglycosides are those which have alkyl groups containing 8 to 10 carbon atoms and having an average degree of polymerization of 1.7 and those which have alkyl groups containing 9 to 11 carbon atoms and having an average degree of polymerization of 1.6.
- alkyl glucose ester sugar cosurfactants are generally disclosed in U.S. Patent Nos. 5,109,127 and 5,190,747, the entire contents of both being incorporated herein by reference. These sugar cosurfactants have the general formula:
- R represents a fatty acid residue of 6 to 20 carbon atoms, preferably 6 to 12 carbon atoms and R 1 represents an alkyl group having 2 to 6 carbon atoms.
- alkyl glucose esters are 1 -ethyl-6- caprylglucoside, 1-ethyl-6-laurylglucoside, 1-butyl-6-caprylglucoside, 1-ethyl- 6-palmitylglucoside and 1-ethyl-6-oleylglucoside.
- aldobionamide sugar cosurfactants are generally disclosed in U.S. Patent No. 5,310,542 and in published European Patent Application No. 550,281 , both of which are incorporated herein by reference.
- An Aldobionamide is generally defined as the amide of an aldobionic acid or aldobionolactone and an aldobionic acid in turn is defined as a sugar substance (e.g., any cyclic sugar) in which the aldehyde group has been replaced by a carboxylic acid which upon drying is capable of cyclizing to form an aldonolactone.
- the aldobionamides can be based on compounds comprising two saccharide units, e.g., lactobionamides, maltobionamides, cellobionamides, melibionamides, or gentiobionamides, or they can be based 8 on compounds comprising more than two saccharide units provided that the polysaccharide has a terminal sugar unit with an aldehyde group available.
- the preferred aldobionamides of the present invention are lactobionamides of the formula:
- R 1 and R 2 are the same or different and are selected from hydrogen and an aliphatic hydrocarbon radical containing up to about 36 carbon atoms (e.g., alkyl groups and alkenyl groups, which groups may also include a heteroatom such as N, O, S, present, for instance, as an amide, carboxy, ether and/or saccharide moiety) except that R and R 2 cannot simultaneously be hydrogen.
- the aliphatic hydrocarbon radical preferably contains up to 24 carbon atoms, most preferably from 8 to 18 carbon atoms.
- lactobionamides are N-propyl lactobionamide, N-pentyl lactobionamide, N-decyl lactobionamide, N-hexadecyl lactobionamide, N- oleyl lactobionamide, N-dodecyl-N-methyl lactobionamide, and N- dodecyloxypropyl lactobionamide.
- gluconamide sugar cosurfactants are generally disclosed in U.S. Patent 5,352,386, the entire contents of which are incorporated herein by reference. These cosurfactants have the general formula: HOCH 2 -(CHOH) m -C(0)-NHR wherein m is an integer from 2 to 5; and R is a straight or branched, saturated or unsaturated aliphatic hydrocarbon having 4 to about 24 carbon atoms, preferably 8 to 24 carbon atoms, which R group can also contain a heteroatom selected from the group consisting of oxygen, nitrogen and sulfur.
- Representative examples of such cosurfactants are N-octylerythronamide, N- 9 decylerythronamide, N-dodecylerythronamide, N-tetradecylerythronamide, N- decylxylonamide and N-dodecylxylonamide.
- glyceramide sugar cosurfactants are generally disclosed in U.S. Patent 5,352,387, the entire contents of which are incorporated herein by reference. These cosurfactants have the general formula:
- R is a C 8 to C 24 straight or branched chained, saturated or unsaturated aliphatic hydrocarbon in which the R group may also be substituted by a heteroatom selected from oxygen, nitrogen and sulfur.
- Representative examples of such cosurfactants are N-octylglyceramide, N- decylglyceramide and N-hexadecylglyceramide.
- the glyceroglycolipid sugar cosurfactants are generally disclosed in U.S. Patent 5,358,656 and published European Patent Application No. 550,279, the disclosure of each of which is incorporated herein by reference.
- the glyceroglycolipids can be of the formula:
- a 1 is a saccharide, preferably having one or more saccharide units, more preferably a mono or disaccharide and most preferably a monosaccharide such as glucose or galactose;
- R and R are the same or different and are hydrogen, a branched or unbranched hydrocarbon radical having from 1 to about 24, preferably from about 6 to about 18 carbon atoms;
- B is OH or a NR 2 R 3 group, wherein R 2 and R 3 may be the same or different and are hydrogen, a branched or unbranched hydrocarbon radical having 1 to 24, preferably from 6 to 18 carbon atoms, and NRR and B are positionally interchangeable.
- cosurfactants are 3- (butylamino)-2-hydroxypropyl- ⁇ -D-galactopyranoside, 3-(octylamino)-2- hydroxypropyl- ⁇ -D-galactopyranoside, 3-(eicosylamino)-2-hydroxypropyl- ⁇ -D- galactopyranoside, 3-(butylamino)-2-hydroxypropyl- ⁇ -D-glucopyranoside, and 3-(pentylamino)-2-hydroxypropyl- ⁇ -D-mannopyranoside.
- Other glyceroglycolipid cosurfactants are disclosed in published
- A'-O-CH ⁇ CH RO-C ⁇ OR wherein A 1 is from 1 to 4 saccharide units and more preferably represents a mono or disaccharide, and most preferably a monosaccharide, for example, glucose or galactose; R and R, are the same or different and are hydrogen, or a branched or unbranched, saturated or unsaturated, hydrocarbon radical having from 1 to 24 carbon atoms, preferably from 6 to 18 carbon atoms.
- cosurfactants are 3-(butyloxy)-2- hydroxypropyl- ⁇ -D-galactopyranoside, 3-(eicosyloxy)-2-hydroxypropyl- ⁇ -D- galactopyranoside, 3-(decyloxy)-2-hydroxypropyl- ⁇ -D-galactopyranoside, 3- (butyloxy)-2-hydroxypropyl- ⁇ -D-glucopyranoside, 3-(octyloxy)-2- hydroxypropyl- ⁇ -D-mannopyranoside, 3-(tetradecyloxy)-2-hydroxypropyl- ⁇ -D- lactoside, 3-(octadecyloxy)-2-hydroxypropyl- ⁇ -D-maltoside, 3-(octyloxy)-2- hydroxypropyl- ⁇ -D-galactotrioside, and 3-(dodecyloxy)-2-hydroxypropyl- ⁇ -D- cellotrioside.
- polyhydroxy fatty acid amide sugar cosurfactants are generally disclosed in U.S. Patent Nos. 5,174,927, 5,223,179 and 5,332,528, the entire disclosure of each of which is incorporated herein by reference.
- the polyhydroxy fatty acid amide surfactant component of the present invention comprises compounds of the structural formula:
- R 2 C(0)N(R 1 )Z wherein: R 1 is H, ⁇ -0 4 hydrocarbyl, 2-hydroxy ethyl, 2-hydroxy propyl or a mixture thereof, preferably ( C 4 alkyl, more preferably C, or C 2 alkyl, most preferably C alkyl (i.e., methyl); and R 2 is a C 5 -C 31 hydrocarbyl, preferably straight chain C 7 -C 19 alkyl or alkenyl, more preferably straight chain C 9 -C 17 alkyl or alkenyl, most preferably straight chain C ⁇ -C ⁇ alkyl or alkenyl, or mixture thereof; and Z is a polyhydroxy hydrocarbyl having a linear hydrocarbyl chain with at least 3 hydroxyls directly connected to the chain, or an alkoxylated derivative (preferably ethoxylated or propoxylated) thereof.
- Z preferably will be derived from a reducing sugar in a reductive amination reaction; more preferably Z is a glycityl.
- Suitable reducing sugars include glucose, fructose, maltose, lactose, galactose, mannose, and xylose.
- raw 11 materials high dextrose corn syrup, high fructose corn syrup, and high maltose corn syrup can be utilized as well as the individual sugars listed above. These corn syrups may yield a mix of sugar components for Z. It should be understood that it is by no means intended to exclude other suitable raw materials.
- Z preferably will be selected from the group consisting of -CH 2 -(CHOH)n-CH 2 OH, -CH(CH 2 OH)-(CHOH) n .
- Most preferred are glycityls wherein n is 4, particularly -CH 2 -(CHOH) 4 -CH 2 OH.
- R 1 can be, for example, N-methyl, N-ethyl, N-propyl, N-isopropyl, N-butyl, N-2-hydroxy ethyl, or N-2-hydroxy propyl.
- R 2 C(0)N ⁇ can be, for example, cocamide, stearamide, oleamide, lauramide, myristamide, capricamide, palmitamide, tallowamide, etc.
- Z can be 1-deoxyglucityl, 2-deoxyfructityl, 1-deoxymaltityl,
- cosurfactants are N-methyl-N-1- deoxyglucityl cocoamide and N-methyl-N-1 -deoxyglucityl tallowamide.
- R is a C 7 -C 21 hydrocarbyl species, i.e., coconut, tallow, palm fatty alkyl and oleyl
- R 1 is a C to C 6 hydrocarbyl or substituted hydrocarbyl species, i.e., N-alkyl-N-(1 ,2-propanediol) and N-hydroxyalkyl-N-1 ,2-propane diol fatty acid amides.
- cosurfactants are the tallow amide of 3-[2-(hydroxyethyl)amino]-1 ,2-propanediol (HEAPD), the palmitate amide of 3-methylamino-1 ,2-propanediol (MAPD) and the lauramide of MAPD.
- HAPD tallow amide of 3-[2-(hydroxyethyl)amino]-1 ,2-propanediol
- MAPD palmitate amide of 3-methylamino-1 ,2-propanediol
- lauramide of MAPD lauramide of MAPD.
- Alkoxylated fatty alcohols include fatty alcohols such as those listed above which are alkoxylated with ethylene oxide, propylene oxide and combinations thereof. 12
- Alkoxylated fatty acids include fatty acids such as those listed above which are alkoxylated with ethylene oxide, propylene oxide and combinations thereof.
- Alkoxylated fatty ethers include fatty ethers such as those listed above which are alkoxylated with ethylene oxide, propylene oxide and combinations thereof.
- Alkoxylated fatty amides include fatty amides such as those listed above which are alkoxylated with ethylene oxide, propylene oxide and combinations thereof.
- Suitable alcohol ethoxylates include C8-18 alcohols ethoxylated with from about 2 to about 30 moles of ethylene oxide.
- Suitable ethoxylated seed oils include those containing from about 1 to about 200 moles of ethylene oxide.
- examples of ethoxylated mineral oils include those containing from about 1 to about 200 moles of ethylene oxide.
- Suitable nonylphenol ethoxylates include those ethoxylated with from about 4 to about 70 moles of ethylene oxide.
- a particularly preferred nonylphenol ethoxylate is a combination of an NP-9 with an NP-6.
- Alkoxylated alkyl phenols include alkyl phenols such as those listed above which are alkoxylated with ethylene oxide, propylene oxide and combinations thereof.
- Ethoxylated glycerides which may be employed in the adjuvant composition of the present invention include those based on C ⁇ fatty acids containing from about 1 to about 200 moles of ethylene oxide.
- Suitable castor oil ethoxylates include those containing from about 1 to about 200 moles of ethylene oxide.
- nonionic surfactants for use in the adjuvant composition of the present invention include a mixture of an alkyl polyglycoside and a castor oil containing from about 5 to about 54 moles of ethylene oxide in a ratio by weight of 1 :2 to about 1 :20.
- the anionic surfactants that can be used in the compositions according to the invention are selected from the group consisting of an 13 ethoxylated partial phosphate ester, an alkyl sulfate and, an alkyl ether sulfate, a branched alkyl benzene sulfonate, a linear alkyl benzene sulfonate and an alpha olefin sulfonate.
- the preferred anionic surfactant is an ethoxylated partial phosphate ester.
- the ethoxylated partial phosphate esters are partial phosphate esters of polyoxyalkylene ethers.
- partial esters are prepared by methods well known to those skilled in the art such as, for example, by reaction of a monofunctional polyoxyalkylene ether with phosphoric acid, diphosphorus pentoxide, polyphosphoric acid, or phosphorus oxytrichloride.
- phosphoric acid diphosphorus pentoxide
- polyphosphoric acid polyphosphoric acid
- phosphorus oxytrichloride phosphorus oxytrichloride
- a preferred ethoxylated partial phosphate ester is phosphoric acid partially esterified with nonyl phenol (EO)-9, (nonyl phenol ethoxylated with 9 moles of ethylene oxide).
- the alkyl sulfates that can be used in the compositions according to the invention are those wherein the alkyl group has from about 6 to about 22 carbon atoms.
- the alkyl ether sulfates that can be used in the compositions according to the invention are those wherein the alkyl group has from about 6 to about 22 carbon atoms.
- the branched alkyl benzene sulfonates that can be used in the compositions according to the invention are those wherein the alkyl group can be branched and has from about 6 to about 22 carbon atoms.
- the linear alkyl benzene sulfonates that can be used in the compositions according to the invention are those wherein the alkyl group is an essentially unbranched alkyl group having from about 6 to about 22 carbon atoms.
- the alpha olefin sulfonates that can be used in the compositions according to the invention are those wherein the alkyl group has from about 6 to about 22 carbon atoms.
- Suitable fertilizer components include, but are not limited to, nitrogenous fertilizers such as urea ammonium nitrate, as well as those of the sulfate type such as liquid ammonium sulfate. It should be noted, however, that any fertilizer suitable for application onto an agricultural substrate, may be utilized, without departing from the spirit of the invention.
- an adjuvant composition containing: (a) from about .5 to about 95% by weight, preferably from about 5 to about 90% by weight, and most preferably from about 10 to about 80% by weight, of an oil component; (b) from about .5 to about 35% by weight, preferably from about 1 to about 25% by weight, and most preferably from about 5 to about 20% by weight, of a nonionic surfactant; (c) from about .1 to about 25% by weight, preferably from about .5 to about 15% by weight, and most preferably from about 1 to about 10% by weight, of an anionic component; and (d) from about .1 to about 70% by weight, preferably from about .5 to about 60% by weight, and most preferably from about 1 to about 50% by weight, of a fertilizer, preferably a nitrogenous fertilizer.
- Auxiliary components may also be added to the adjuvant composition of the present invention, in order to further enhance the properties thereof.
- examples thereof include, but are not limited to, water-soluble silicone surfactants, oil-soluble silicone surfactants, cationic surfactants, amphoteric surfactants, and the like.
- Suitable water-soluble silicone surfactants include, but are not limited to, EO/PO polyether-trisiloxane copolymers such as BREAKTHRU® S240, commercially available from Goldschmidt Chemical Corp.
- Suitable oil-soluble silicone surfactants include, but are not limited to,
- EO/PO polyether-polymethylsiloxane-copolymers such as BREAKTHRU® OE 441 , commercially available from Goldschmidt ChemicaLCorp.
- Anionic surfactants which may be employed include, but are not limited to, phosphate esters, an ethoxylated partial phosphate ester, an alkyl sulfate and, an alkyl ether sulfate, a branched alkyl benzene sulfonate, a linear alkyl benzene sulfonate and an alpha olefin sulfonate.
- the preferred anionic surfactant is an ethoxylated partial phosphate ester.
- the ethoxylated partial phosphate esters are partial phosphate esters of polyoxyalkylene ethers.
- partial esters are prepared by methods well known to those skilled in the art such as, for example, by reaction of a monofunctional polyoxyalkylene ether with phosphoric acid, diphosphorus pentoxide, polyphosphoric acid, or phosphorus oxytrichloride. These partial phosphate esters are described in 15
- a preferred ethoxylated partial phosphate ester is phosphoric acid partially esterified with nonyl phenol (EO)-9, (nonyl phenol ethoxylated with 9 moles of ethylene oxide).
- Cationic surfactants which may be employed include, but are not limited to, ethoxylated amines such as ethoxylated tallow amine.
- Amphoteric surfactants which may be employed include, but are not limited to, amino acids and their derivatives, amino acid salts, imidazolinium derivatives, alkyl betaines and amidopropyl analogues. In the event that such auxiliary components are employed, they will be present in the adjuvant composition of the present invention in an amount ranging from about 1 to about 25% by weight, preferably from about 4 to about 20% by weight, and most preferably from about 7 to about 18% by weight.
- methyl or ethyl esters of fatty acids or other pH sensitive components such as sulfonylurea pesticides
- the pH may be adjusted by using, for example, potassium hydroxide, ammonium hydroxide, sodium hydroxide, triethanolamine, monoethanolamine and aminoethylethanolamine.
- the adjuvant composition thus formed can then be combined with a biologically active substance such as a fungicide, bactericide, bacteriostat, herbicide/plant growth regulator, and the like, to formulate an agricultural composition for use on agricultural substrates.
- a biologically active substance such as a fungicide, bactericide, bacteriostat, herbicide/plant growth regulator, and the like.
- Suitable biologically active materials which can be used to make agricultural compositions according to the invention include, but are not limited to, fungicides such as 3,3'-ethylenebis (tetrahydro-4,6-dimethyl-2H-1 ,3,5-thiadiazine-2-thione), zinc or manganese ethylenebis(dithiocarbamate), bis-(dimethyldithiocarbamoyl)disulfide, zinc propylenebis (dithiocarbamate), bis(dimethyldithiocarbamoyl) 16 ethylenediamine; nickel dimethyldithiocarbamate, methyl-1(butylcarbamoyl)-2-benzimidazolecarbamate,
- fungicides such as 3,3'-ethylenebis (tetrahydro-4,6-dimethyl-2H-1 ,3,5-thiadiazine-2-thione), zinc or manganese ethylenebis(dithiocarbamate), bis-(dimethyldithiocar
- 5-methyl-10-butoxycarbonylamino-10, 11 -dehydrodibenzo (b,f)azepine pyridine fungicides such as zinc bis(1-hydroxy-2(1H)pyridinethionate and 2-pyridinethiol-1 -oxide sodium salt;
- N-(2,6-diethylphenyl)-4-methylphthalimide N-(2,6-diethylphenyl)-4-methylphthalimide; dicarboxyimide fungicides such as
- Plant growth regulators which may also be employed include but are not limited to N-methoxycaronyl-N'-4-methylphenylcarbamoylethylisourea and
- 2-methylthio-4-ethylamino-6-isopropylamino-s-triazine phenoxy herbicides such as 2,4-dichlorophenoxyacetic acid and methyl, ethyl, and butyl esters thereof.
- 2-chloro-4-methylphenoxyacetic acid 4-chloro-2-methylphenoxyacetic acid and ethyl 2-methyl-4-chlorophenoxybutylate
- diphenylether herbicides such as 2,4,6-trichlorophenyl-4'-nitrophenylether,2,4-dichlorophenyl-4'-nitrophenylethe r and 3,5-dimethylphenyl-4'-nitrophenylether
- urea herbicides such as
- the agricultural compositions according to the invention may also contain, for example, dyes, additional cosurfactants, emulsifiers and solvents where required.
- the present invention also provides a process for treating an agricultural substrate involving contacting the substrate with the above- disclosed agricultural composition. 19
- the above-formulated adjuvant compositions exhibited acceptable storage stability, in view of the presence of a fertilizer component in the composition.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU37404/99A AU3740499A (en) | 1998-04-29 | 1999-04-29 | Agricultural adjuvant |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US8339698P | 1998-04-29 | 1998-04-29 | |
US60/083,396 | 1998-04-29 | ||
US29204999A | 1999-04-14 | 1999-04-14 | |
US09/292,049 | 1999-04-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1999055645A1 true WO1999055645A1 (en) | 1999-11-04 |
Family
ID=26769244
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1999/006553 WO1999055645A1 (en) | 1998-04-29 | 1999-04-29 | Agricultural adjuvant |
Country Status (2)
Country | Link |
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AU (1) | AU3740499A (en) |
WO (1) | WO1999055645A1 (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002069705A1 (en) * | 2001-02-19 | 2002-09-12 | Cognis Deutschland Gmbh & Co. Kg | Adjuvants for biological pesticides |
WO2002090295A1 (en) * | 2001-05-04 | 2002-11-14 | Norsk Hydro Asa | Agricultural composition and conditioning agent |
CN102186943B (en) * | 2008-10-15 | 2015-04-29 | 纳尔科公司 | A composition for dust control and limiting moisture re-absorption |
EP2894963A4 (en) * | 2012-09-13 | 2016-06-01 | Rhodia Operations | Wettable peat moss, method of preparation, and method of use |
EP3103782A1 (en) | 2015-06-10 | 2016-12-14 | Przedsiebiorstwo Produkcyjno-Consultingowe Adob Sp. z o.o. s.k. | A combination of surfactants for liquid aqueous fertilizer composition |
WO2020154687A1 (en) * | 2019-01-25 | 2020-07-30 | AMVAC Hong Kong Limited | Agricultural adjuvant comprising microfibrillated cellulose |
EP4064839A4 (en) * | 2019-11-26 | 2023-12-06 | Oro Agri Europe S.A. | An agricultural adjuvant |
US11998005B2 (en) | 2018-06-15 | 2024-06-04 | Nouryon Chemicals International B.V. | Herbicidal formulations comprising glyphosate and COTE-based adjuvants |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4997642A (en) * | 1981-12-24 | 1991-03-05 | Sandoz Ltd. | Stable oil-in-water emulsions |
US5123950A (en) * | 1987-12-08 | 1992-06-23 | Rikagaku Kenkyusho | Coated agricultural chemicals |
-
1999
- 1999-04-29 WO PCT/US1999/006553 patent/WO1999055645A1/en active Application Filing
- 1999-04-29 AU AU37404/99A patent/AU3740499A/en not_active Abandoned
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4997642A (en) * | 1981-12-24 | 1991-03-05 | Sandoz Ltd. | Stable oil-in-water emulsions |
US5123950A (en) * | 1987-12-08 | 1992-06-23 | Rikagaku Kenkyusho | Coated agricultural chemicals |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002069705A1 (en) * | 2001-02-19 | 2002-09-12 | Cognis Deutschland Gmbh & Co. Kg | Adjuvants for biological pesticides |
WO2002090295A1 (en) * | 2001-05-04 | 2002-11-14 | Norsk Hydro Asa | Agricultural composition and conditioning agent |
HRP20030862B1 (en) * | 2001-05-04 | 2009-06-30 | Yara International Asa | Agricultural composition and conditioning agent |
CN102186943B (en) * | 2008-10-15 | 2015-04-29 | 纳尔科公司 | A composition for dust control and limiting moisture re-absorption |
EP2894963A4 (en) * | 2012-09-13 | 2016-06-01 | Rhodia Operations | Wettable peat moss, method of preparation, and method of use |
EP3103782A1 (en) | 2015-06-10 | 2016-12-14 | Przedsiebiorstwo Produkcyjno-Consultingowe Adob Sp. z o.o. s.k. | A combination of surfactants for liquid aqueous fertilizer composition |
US11998005B2 (en) | 2018-06-15 | 2024-06-04 | Nouryon Chemicals International B.V. | Herbicidal formulations comprising glyphosate and COTE-based adjuvants |
WO2020154687A1 (en) * | 2019-01-25 | 2020-07-30 | AMVAC Hong Kong Limited | Agricultural adjuvant comprising microfibrillated cellulose |
US11358905B2 (en) | 2019-01-25 | 2022-06-14 | Amvac Chemical Corporation | Microfibrillated cellulose as rheology modifier in high ionic strength agricultural formulations |
EP4064839A4 (en) * | 2019-11-26 | 2023-12-06 | Oro Agri Europe S.A. | An agricultural adjuvant |
Also Published As
Publication number | Publication date |
---|---|
AU3740499A (en) | 1999-11-16 |
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