NZ626024B2 - Macrostructure forming surfactants useful as spray drift control agents in pesticide spraying applications - Google Patents
Macrostructure forming surfactants useful as spray drift control agents in pesticide spraying applications Download PDFInfo
- Publication number
- NZ626024B2 NZ626024B2 NZ626024A NZ62602412A NZ626024B2 NZ 626024 B2 NZ626024 B2 NZ 626024B2 NZ 626024 A NZ626024 A NZ 626024A NZ 62602412 A NZ62602412 A NZ 62602412A NZ 626024 B2 NZ626024 B2 NZ 626024B2
- Authority
- NZ
- New Zealand
- Prior art keywords
- alkyl
- oil
- saturated
- alkyl group
- surfactant
- Prior art date
Links
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 109
- 239000007921 spray Substances 0.000 title claims abstract description 94
- 238000005507 spraying Methods 0.000 title claims abstract description 42
- 239000003795 chemical substances by application Substances 0.000 title description 17
- 239000000575 pesticide Substances 0.000 title description 16
- 239000002245 particle Substances 0.000 claims abstract description 70
- 239000003905 agrochemical Substances 0.000 claims abstract description 31
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000003595 mist Substances 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 137
- 239000003921 oil Substances 0.000 claims description 74
- 239000000203 mixture Substances 0.000 claims description 46
- 239000003760 tallow Substances 0.000 claims description 44
- -1 ate Chemical compound 0.000 claims description 39
- 235000010469 Glycine max Nutrition 0.000 claims description 36
- 241000209149 Zea Species 0.000 claims description 36
- 235000017060 Arachis glabrata Nutrition 0.000 claims description 35
- 240000005781 Arachis hypogaea Species 0.000 claims description 35
- 235000010777 Arachis hypogaea Nutrition 0.000 claims description 35
- 235000018262 Arachis monticola Nutrition 0.000 claims description 35
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 35
- 235000005822 corn Nutrition 0.000 claims description 35
- 235000005824 corn Nutrition 0.000 claims description 35
- 235000020232 peanut Nutrition 0.000 claims description 35
- 235000004443 Ricinus communis Nutrition 0.000 claims description 33
- KWIUHFFTVRNATP-UHFFFAOYSA-N Trimethylglycine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 19
- 238000009472 formulation Methods 0.000 claims description 15
- 150000001408 amides Chemical class 0.000 claims description 14
- 230000002363 herbicidal Effects 0.000 claims description 14
- 239000004009 herbicide Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 235000013162 Cocos nucifera Nutrition 0.000 claims description 13
- 240000007170 Cocos nucifera Species 0.000 claims description 13
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 13
- 239000000194 fatty acid Substances 0.000 claims description 13
- 238000007046 ethoxylation reaction Methods 0.000 claims description 12
- 239000011780 sodium chloride Substances 0.000 claims description 12
- 229960003237 betaine Drugs 0.000 claims description 10
- 150000003512 tertiary amines Chemical class 0.000 claims description 10
- RPNUMPOLZDHAAY-UHFFFAOYSA-N DETA Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 7
- NEHMKBQYUWJMIP-UHFFFAOYSA-N Chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 7
- 229940050176 Methyl Chloride Drugs 0.000 claims description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 7
- 101700082413 tant Proteins 0.000 claims description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 6
- 239000005562 Glyphosate Substances 0.000 claims description 6
- 150000004665 fatty acids Chemical class 0.000 claims description 6
- 229940097068 glyphosate Drugs 0.000 claims description 6
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 6
- 239000005561 Glufosinate Substances 0.000 claims description 5
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N Glufosinate Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 claims description 5
- ZBCBWPMODOFKDW-UHFFFAOYSA-N Diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N ethanolamine Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
- 239000005631 2,4-D Substances 0.000 claims description 3
- 239000005504 Dicamba Substances 0.000 claims description 3
- IWEDIXLBFLAXBO-UHFFFAOYSA-N Dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- XDDAORKBJWWYJS-UHFFFAOYSA-O Glyphosate Chemical compound OC(=O)C[NH2+]CP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-O 0.000 claims 1
- 241000229754 Iva xanthiifolia Species 0.000 claims 1
- 229940035295 Ting Drugs 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 239000006185 dispersion Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 230000000694 effects Effects 0.000 description 12
- IUQJDHJVPLLKFL-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)acetate;dimethylazanium Chemical compound CNC.OC(=O)COC1=CC=C(Cl)C=C1Cl IUQJDHJVPLLKFL-UHFFFAOYSA-N 0.000 description 11
- 238000003972 agrochemical formulation Methods 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 239000002502 liposome Substances 0.000 description 8
- XDDAORKBJWWYJS-UHFFFAOYSA-N Glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 6
- 150000003973 alkyl amines Chemical class 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 229920002907 Guar gum Polymers 0.000 description 5
- 239000000665 guar gum Substances 0.000 description 5
- 235000010417 guar gum Nutrition 0.000 description 5
- 229960002154 guar gum Drugs 0.000 description 5
- 238000005429 turbidity Methods 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- MXWJVTOOROXGIU-UHFFFAOYSA-N Atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 3
- 229920000126 Latex Polymers 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000749 insecticidal Effects 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000004816 latex Substances 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- 238000010587 phase diagram Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- UCSJYZPVAKXKNQ-HZYVHMACSA-N 1-[(1S,2R,3R,4S,5R,6R)-3-carbamimidamido-6-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- LKPLKUMXSAEKID-UHFFFAOYSA-N Pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 2
- JUVIOZPCNVVQFO-HBGVWJBISA-N Rotenone Natural products O([C@H](CC1=C2O3)C(C)=C)C1=CC=C2C(=O)[C@@H]1[C@H]3COC2=C1C=C(OC)C(OC)=C2 JUVIOZPCNVVQFO-HBGVWJBISA-N 0.000 description 2
- QMGVPVSNSZLJIA-FVWCLLPLSA-N Strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 2
- BFWMWWXRWVJXSE-UHFFFAOYSA-M Triphenyltin hydroxide Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFWMWWXRWVJXSE-UHFFFAOYSA-M 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 230000000855 fungicidal Effects 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- INFDPOAKFNIJBF-UHFFFAOYSA-N paraquat Chemical compound C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 INFDPOAKFNIJBF-UHFFFAOYSA-N 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XERJKGMBORTKEO-VZUCSPMQSA-N (1E)-2-(ethylcarbamoylamino)-N-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 description 1
- SAPGTCDSBGMXCD-UHFFFAOYSA-N (2-chlorophenyl)-(4-fluorophenyl)-pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(F)C=C1 SAPGTCDSBGMXCD-UHFFFAOYSA-N 0.000 description 1
- DBTMGCOVALSLOR-DEVYUCJPSA-N (2S,3R,4S,5R,6R)-4-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](CO)O[C@H](O)[C@@H]2O)O)O[C@H](CO)[C@H]1O DBTMGCOVALSLOR-DEVYUCJPSA-N 0.000 description 1
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3aR,7aS)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- OYIKARCXOQLFHF-UHFFFAOYSA-N (5-cyclopropyl-1,2-oxazol-4-yl)-[2-methylsulfonyl-4-(trifluoromethyl)phenyl]methanone Chemical compound CS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 OYIKARCXOQLFHF-UHFFFAOYSA-N 0.000 description 1
- PPDBOQMNKNNODG-NTEUORMPSA-N (5E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol Chemical compound C1=NC=NN1CC1(O)C(C)(C)CC\C1=C/C1=CC=C(Cl)C=C1 PPDBOQMNKNNODG-NTEUORMPSA-N 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- CKPCAYZTYMHQEX-NBVRZTHBSA-N (E)-1-(2,4-dichlorophenyl)-N-methoxy-2-pyridin-3-ylethanimine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=N/OC)/CC1=CC=CN=C1 CKPCAYZTYMHQEX-NBVRZTHBSA-N 0.000 description 1
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- CJPQIRJHIZUAQP-INIZCTEOSA-N (S)-benalaxyl Chemical compound CC=1C=CC=C(C)C=1N([C@@H](C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-INIZCTEOSA-N 0.000 description 1
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- VJYIFXVZLXQVHO-UHFFFAOYSA-N 1-(2-chlorophenyl)sulfonyl-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 VJYIFXVZLXQVHO-UHFFFAOYSA-N 0.000 description 1
- JWUCHKBSVLQQCO-UHFFFAOYSA-N 1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(F)C=CC=1C(C=1C(=CC=CC=1)F)(O)CN1C=NC=N1 JWUCHKBSVLQQCO-UHFFFAOYSA-N 0.000 description 1
- LQDARGUHUSPFNL-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COC(F)(F)C(F)F)CN1C=NC=N1 LQDARGUHUSPFNL-UHFFFAOYSA-N 0.000 description 1
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 1
- MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 description 1
- PFFIDZXUXFLSSR-UHFFFAOYSA-N 1-methyl-N-[2-(4-methylpentan-2-yl)-3-thienyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound S1C=CC(NC(=O)C=2C(=NN(C)C=2)C(F)(F)F)=C1C(C)CC(C)C PFFIDZXUXFLSSR-UHFFFAOYSA-N 0.000 description 1
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- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-Dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 1
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 1
- KWLVWJPJKJMCSH-UHFFFAOYSA-N 2-(4-chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-yn-1-yloxy)acetamide Chemical compound C1=C(OCC#C)C(OC)=CC(CCNC(=O)C(OCC#C)C=2C=CC(Cl)=CC=2)=C1 KWLVWJPJKJMCSH-UHFFFAOYSA-N 0.000 description 1
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- IRCMYGHHKLLGHV-UHFFFAOYSA-N 2-ethoxy-3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl methanesulfonate Chemical compound C1=C(OS(C)(=O)=O)C=C2C(C)(C)C(OCC)OC2=C1 IRCMYGHHKLLGHV-UHFFFAOYSA-N 0.000 description 1
- 229940044120 2-n-octyl-4-isothiazolin-3-one Drugs 0.000 description 1
- SOUGWDPPRBKJEX-UHFFFAOYSA-N 3,5-dichloro-N-(1-chloro-3-methyl-2-oxopentan-3-yl)-4-methylbenzamide Chemical compound ClCC(=O)C(C)(CC)NC(=O)C1=CC(Cl)=C(C)C(Cl)=C1 SOUGWDPPRBKJEX-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
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- VJQYLJSMBWXGDV-UHFFFAOYSA-N tiadinil Chemical compound N1=NSC(C(=O)NC=2C=C(Cl)C(C)=CC=2)=C1C VJQYLJSMBWXGDV-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical group COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);N-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 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
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
-
- 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
- A01N25/02—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 liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- 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
- A01N25/02—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 liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
- A01N25/06—Aerosols
-
- 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
- A01N25/30—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 characterised by the surfactants
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
-
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
- A01N39/04—Aryloxy-acetic acids; Derivatives thereof
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
-
- 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
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
- A01N59/16—Heavy metals; Compounds thereof
- A01N59/20—Copper
Abstract
The disclosure relates to an aqueous agrochemical spray solution comprising at least one agrochemical active and at least one surfactant, wherein said spray solution comprises a dispersed phase comprising dispersed particles which have an average particle size between 1 to 100 microns, wherein the concentration of said dispersed particles is from 0.001 to 5 wt%, and wherein said nitrogen containing surfactant comprises a compound selected from the group defined in the specification, and wherein said aqueous agrochemical spray solution is capable of reducing the volume of the fine droplets in mist whose size is less than 150 microns during spraying by at least 20% compared to the same aqueous spray solution without the presence of the said surfactant. The disclosure also relates to a method of reducing spray drift using said solution. oncentration of said dispersed particles is from 0.001 to 5 wt%, and wherein said nitrogen containing surfactant comprises a compound selected from the group defined in the specification, and wherein said aqueous agrochemical spray solution is capable of reducing the volume of the fine droplets in mist whose size is less than 150 microns during spraying by at least 20% compared to the same aqueous spray solution without the presence of the said surfactant. The disclosure also relates to a method of reducing spray drift using said solution.
Description
tructure forming surfactants useful as spray drift control agents in pesticide
spraying applications
Field of the Invention
The present invention relates to a surfactant composition and a method capable of
forming a dispersion system with macrostructures in s environment resulting in reduced
number of fine droplets in mist during ng agricultural pesticide solutions when the size of
the sed particles is between 1 — 100 um and the concentration of the dispersed particles is
between 0.001 — 5 wt%. NZ 723294 is a divisional from the present application. The
description of the present invention and the invention ofNZ 723294 is retained herein for claiity
and completeness.
Background of the Invention
The drift of spray from pesticide applications can expose people, wildlife, and the
environment to pesticide es that can cause health and environmental effects and property
damage. Spray drift can prevent a substantial portion of the pesticide from reaching its ed
target, requiring more of the pesticide to e adequate coverage of the target.
In practice, two chemical approaches have been used to reduce the amount of drifting of
small droplets during spraying of an aqueous pesticide solution.
In the first approach, high molecular weight water soluble rs such as a guar gum,
xanthan gum, polyacrylamides, polyethylene oxide, and other ethylenically unsaturated
monomers are employed as drift l agents in the agricultural application. It has been
lly accepted that polymers which give optimum spray drift control are either non—ionic
(e.g., acrylamide homopolymer) or have relatively low anionic content (e. g. 5 to 30 wt. %) and
also have vely high intrinsic viscosity, for instance above 6 dl/g. Guar gum is one of the
most widely used drift control agent in the current world market. It is believed that the rs
produce an enhanced extensional viscosity during spraying which is the main reason for the
improved drift control over spraying water. Unfortunately, these polymers have various
drawbacks. One drawback is that their solutions tend to Show rsible lose of their y due
to the fact that high molecular weight polymers undergo mechanical degradation of the polymer
chain. Another drawback is that it takes a long time for the high molecular weight polymers to
evenly disperse or dissolve in s liquids which may lead to many large and undissolved
particles that could plug the spraying nozzle. Still another drawback of polymers as drift control
agents is that the polymers are difficult to build into a high salt premix pesticide formulation
without gelling or phase separation. In addition, the polymer drift control agents perform mainly
one task — to control drift of small droplets during spraying.
In the second approach, a crop oil concentrate (COC) is employed which contains an
emulsifier and a hydrophobic substance such as a mineral oil or a methyl ester. COC can forms
oil-in—water (o/w) ons upon dilution in water which can reduce the fine droplets during
spraying, hence for its application as a drift control agent. r, CDC is not recommended if
the agrochemical formulation is a herbicide and contains a water soluble salts as the active
ingredients such as isopropylamine salt of glyphosate because COC may reduce the efficacy of
the active ient.
Spray pattern plays an important role in small ts drifting. When water is sprayed,
many small liquid droplets form a mist which easily drifts away with wind. When an aqueous
spraying solution containing a drift control agent such as guar gum is sprayed, the sprayed
pattern is modified so that the number of small droplets is much d. Reduction of the
number of small droplets increases the size of the droplets when the spray volume remains the
same. In fact, the size increase in a typical spraying solution containing guar gum as the drift
control agent is often too much so’that there are a lot of coarse droplets which tend to bounce off
the plant leave and be wasted. Over the years, researchers have discovered that the optimum
spray n has a droplet size distribution between 100 — 400 um.
It is the object of the claimed invention to provide a surfactant composition and a method
capable of forming a dispersion system with macrostructures in aqueous environment resulting in
reduced number of fine droplets in mist during spraying agricultural pesticide solutions, n
the size of the sed particles is between 1 — 100 um and the concentration of the dispersed
particles is between 0.001 — 5 wt%, or to at least provide the public with a useful .
Summary of the Invention
In one aspect, there is provided an aqueous agrochemical spray solution comprising at
least one agrochemical active and at least one nitrogen containing surfactant, wherein said
spray
solution comprises a sed phase comprising sed particles which have an average
particle size between 1 to 100 microns, wherein the concentration of said dispersed particles is
[followed by page 2a]
from 0.001 to 5 wt%, and wherein said nitrogen containing surfactant ses a
compound selected from the group consisting of:
(i) a di-alkyl di-methyl quaternary surfactant with a counterion of chloride, bromide,
methylsulfate, carbonate, or bicarbonate, wherein the alkyl group is 2, saturated or non-
saturated, linear or branched alkyl group derived from oil of coco, soy, palm, castor, tallow, corn,
lard, peanut or tall, including the epoxydized version of the oil;
(ii) an alkyl dimethylamidopropylamine n the alkyl group is C 12-C22, saturated or
non-saturated, linear or branched alkyl group derived from oil of coco, soy, coconut, palm,
castor, tallow, corn, lard, peanut or tall, including the epoxydized version of the oil;
(iii) an alkyl dimethylamidopropylamine oxide or alkyl dimethylamidopropylamine
betaine wherein the alkyl group is 2, saturated or non~saturated, linear or ed alkyl
group derived from oil of coco, soy, palm, castor, tallow, corn, lard, peanut or tall, including the
epoxydized version of the oil;
(iv) an alkyl amidoamine ethoxylate wherein the alkyl amidoamine ethoxylate is a
product derived from alkyl fatty acid and diethylenetriamine followed by ethoxylation, and
wherein the alkyl group is Cl2-C22, saturated or non-saturated, linear or branched alkyl
group
derived from oil of coco, soy, coconut, palm, castor, tallow, corn, lard, peanut or tall, including
the epoxydized n of the oil;
(v) an alkyl oxylated with 2E0 methyl chloride nary surfactant, wherein the
alkyl group is Cl6—C22, saturated or non-saturated, linear or branched alkyl group derived from
oil of coco, soy, palm, , tallow, corn, lard, peanut or tall, including the ized version
of the oil;
(Vi) a tertiary amine surfactant of the formula:
R1 R3
wherein R1 represents a straight or branched chain (Cu—C22) alkyl and R2 and R3 independently
[followed by page 2b]
represent a straight or branched chain (C1-C22) alkyl;
(vii) a tertiary amine oxide surfactant of the formula:
R4\ i /R6
wherein R4 is a straight or branched chain (Clo-C22) alkyl or an alkyletherpropyl, and R5 and R6
independently are ht or branched chain (C1-C2?) alkyl or lates or propoxylates of the
formula:
I’m/i C2H4OihH 37:}C2H3(CH3)OtH
wherein n is an integer from 1 to 20;
(viii) an alkoxylated amineoxide derived from alkoxylated alkylamine, wherein the alkyl
group is C12-C22, ted or non-saturated, linear or branched alkyl group derived from oil of
coco, soy, palm, castor, tallow, corn, lard, peanut or tall, including the epoxydized version of the
oil; and
(ix) an alkoxylated amide.
In a further aspect, there is provided a method of reducing the spray drift of an aqueous
agrochemical spray solution upon ng with a spraying apparatus, which ses adding at
least one nitrogen containing tant to said aqueous agrochemical spray solution in an
amount effective to form a dispersed phase comprising dispersed particles which have an
e particle size between 1 to 100 microns, wherein the concentration of said dispersed
particles is from 0.001 to 5 wt%, and wherein said s spray solution is capable of reducing
the volume of the fine droplets in mist whose size is less than 150 microns during spraying by at
least 20% compared to the same aqueous spray solution Without the presence of the said
[followed by page 20]
surfactant, and n said nitrogen containing surfactant comprises a compound
selected from the group consisting of:
(i) a di-alkyl hyl quaternary surfactant with a counterion of chloride, bromide,
methylsulfate, carbonate, or bicarbonate, wherein the alkyl group is C12-C22, saturated or non-
saturated, linear or branched alkyl group derived from oil of coco, soy, palm, castor, tallow, corn,
lard, peanut or tall, including the epoxydized version of the oil;
(ii) an alkyl dimethylamidopropylamine wherein the alkyl group is C12-C22, saturated or
non-saturated, linear or branched alkyl group derived from oil of coco, soy, coconut, palm,
castor, tallow, corn, lard, peanut or tall, including the epoxydized version of the oil;
(iii) an alkyl dimethylamidopropylamine oxide or alkyl dimethylamidopropylamine
betaine wherein the alkyl group is 2, saturated or non—saturated, linear or branched alkyl
group d from oil of coco, soy, palm, castor, tallow, corn, lard, peanut or tall, including the
ized n of the oil
(iv) an alkyl amidoamine ethoxylate wherein the alkyl amidoamine ethoxylate is a
product derived from alkyl fatty acid and diethylenetriamine ed by ethoxylation, and
wherein the alkyl group is C12—C22, saturated or non-saturated, linear or branched alkyl group
derived from oil of coco, soy, coconut, palm, castor, tallow, corn, lard, peanut or tall, including
the epoxydized n of the oil
(V) an alkyl di—ethoxylated with 2130 methyl chloride quaternary surfactant, wherein the
alkyl group is C16—C22, saturated or non—saturated, linear or branched alkyl group derived from
oil of coco, soy, palm, castor, tallow, corn, lard, peanut or tall, including the epoxydized version
of the oil;
(Vi) a ry amine surfactant of the a:
R1 R3
wherein R1 represents a straight or branched chain (Cu—C22) alkyl and R2 and R3 independently
[followed by page 2d]
represent a straight or branched chain (C1-C22) alkyl;
(vii) a ry amine oxide surfactant of the formula:
R4\ I /R6
wherein R4 is a straight or branched chain (Clo-C22) alkyl or an alkyletherpropyl, and RS and R6
ndently are ht or branched chain (Cl—ng) alkyl or ethoxylates or propoxylates of the
formula:
14C2H4OEH gACZHfiCHQO n H
wherein n is an integer from 1 to 20;
(viii) an alkoxylated amineoxide d from alkoxylated alkylamine, wherein the alkyl
group is C12-C22, saturated or non-saturated, linear or branched alkyl group derived from oil of
coco, soy, palm, castor, tallow, corn, lard, peanut or tall, including the epoxydized version of the
oil; and
(ix) an an lated amide.
In a further aspect, there is provided a use of a en containing surfactant in an
aqueous agrochemical spray solution comprising at least one agrochemical active in an amount
effective to form a dispersed phase comprising dispersed particles which have an average
particle size between 1 to 100 s, wherein the concentration of said dispersed particles is
from 0.001 to 5 wt%, to provide an aqueous spray solution that has a reduced volume of the fine
droplets in mist whose size is less than 150 microns during spraying of at least 20% compared to
the volume of the fine droplets in mist whose size is less than 150 microns in the same aqueous
spray solution without said surfactant, and wherein said nitrogen containing surfactant comprises
a compound selected from the group consisting of:
[followed by page 2e]
(i) a di-alkyl di-methyl nary surfactant with a counterion of chloride, bromide,
methylsulfate, carbonate, or bicarbonate, wherein the alkyl group is C12—C22, saturated or non-
saturated, linear or branched alkyl group derived from oil of coco, soy, palm, castor, tallow, corn,
lard, peanut or tall, including the epoxydized version of the oil;
(ii) an alkyl dimethylamidopropylamine wherein the alkyl group is C12—C22, saturated
or non—saturated, linear or branched alkyl group derived from oil of coco, soy, coconut, palm,
castor, , corn, lard, peanut or tall, including the epoxydized version of the oil;
(iii) an alkyl dimethylamidopropylamine oxide or alkyl dimethylamidopropylamine
e wherein the alkyl group is ClZ—C22, saturated or non—saturated, linear or ed alkyl
group derived from oil of coco, soy, palm, castor, tallow, corn, lard, peanut or tall, including the
epoxydized version of the oil;
(iv) an alkyl amidoamine late wherein the alkyl amidoamine ethoxylate is a
product derived from alkyl fatty acid and diethylenetriamine followed by lation, and
wherein the alkyl group is C12-C22, saturated or turated, linear or branched alkyl group
derived from oil of coco, soy, coconut, palm, castor, tallow, corn, lard, peanut or tall, including
the ized version of the oil;
(v) an alkyl di—ethoxylated with 2E0 methyl chloride quaternary surfactant, wherein the
alkyl group is Cl6—C22, saturated or non-saturated, linear or branched alkyl group derived from
oil of coco, soy, palm, castor, tallow, corn, lard, peanut or tall, including the epoxydized n
of the oil;
(vi) a tertiary amine surfactant of the formula:
R1 R3
wherein R1 represents a straight or branched chain (Cu-C22) alkyl and R2 and R3 independently
represent a straight or branched chain (Cl-sz) alkyl;
[followed by page 2f]
(vii) a tertiary amine oxide surfactant of the formula:
R4\ I /R6
wherein R4 is a straight or branched chain (Clo—C22) alkyl or an alkyletherpropyl, and R5 and R6
independently are straight or branched chain (Cl-sz) alkyl or ethoxylates or propoxylates of the
formula:
214C2H4OLEH E,{C2H3(CH3)O n H
wherein n is an r from 1 to 20;
(viii) an alkoxylated amineoxide derived from alkoxylated alkylamine, wherein the alkyl
group is 2, ted or non-saturated, linear or branched alkyl group derived from oil of
coco, soy, palm, , tallow, corn, lard, peanut or tall, including the epoxydized version of the
oil; and
(ix) an alkoxylated amide.
The present ion relates to a surfactant composition and a method capable of
g a dispersion system with macrostructures in aqueous environment resulting in reduced
number of fine droplets in mist during spraying agricultural pesticide solutions, wherein the size
of the dispersed particles is between 1 -— 100 um and the concentration of the dispersed particles
is between 0.001 — 5 wt%.
[followed by page 3]
The present invention also relates to an agrochemical formulation sing an active
ingredient and at least one surfactant, wherein the said agrochemical formulation is capable of
forming a aqueous agrochemical spray solution containing a dispersed phase sing
dispersed particles which have an average particle size between 1 to 100 microns, wherein the
concentration of said dispersed particles is from about 0,001 to 5 wt%, and wherein said
aqueous
spray on is e of reducing the volume of the fine droplets in mist whose size is less
than 150 s during spraying by at least 20% compared to the same
aqueous spray solution
without the presence of the said surfactant.
The present invention fiarther relates to an aqueous agrochemical
spray solution
comprising at least one emical active and at least one surfactant, wherein said spray
on comprises a dispersed phase sing dispersed particles which have an
average
particle size between 1 to 100 microns, n the concentration of said dispersed particles is
from about 0.001 to 5 wt%, and wherein said s agrochemical
spray solution is capable of
ng the volume ofthe fine droplets in mist whose size is less than 150 microns during
spraying by at least 20% compared to the same aqueous spray solution without the presence of
the said surfactant.
The present invention also relates to a method of reducing the
spray drift of an aqueous
agrochemical spray solution upon spraying with a spraying apparatus, which comprises adding at
least one surfactant to said aqueous agrochemical spray solution in an amount effective to form
dispersed phase comprising dispersed particles which have an average particle size between 1 to
100 microns, wherein the concentration of said dispersed particles is from about 0.001 to 5 wt%,
and wherein said aqueous spray solution is capable of reducing the volume of the fine droplets in
mist whose size is less than 150 s during spraying by at least 20% ed to the
same
aqueous spray solution t the presence of the said tant.
Detailed Description ofthe Invention
One embodiment ofthe present invention relates to a ready to
spray agrochemical
formulation, wherein said agrochemical formulation is a dispersion comprising a pesticide, a
surfactant, and water capable of reducing drift during ng.
Another embodiment ofthe present invention relates to a concentrated agrochemical
formulation comprising a pesticide and a surfactant, wherein said concentrated agrochemical
WO 98220
formulation is capable of forming a dispersion when diluted in water, wherein said dispersion is
e ofreducing drift during spraying. The concentrated agrochemical formulation can be a
solid formulation, a clear liquid formulation, or a stable turbid liquid formulation.
Still r embodiment of the present ion relates to a surfactant capable of
forming a dispersion when added into a spray tank to form the ready to spray aqueous
agro chemical formulation, wherein said dispersion is capable of reducing drift during spraying.
cally, in the above mentioned embodiments the said dispersion is characterized in
having a dispersed particle size from l — 100 um and a tration of the dispersed particles
from about 0.001% to 5 wt%, in another embodiment from about 0.001% to 0.1%, still in
another embodiment from about 0.01% to 1%, and yet still in another embodiment from 1% to
3%, and wherein said formulation is capable of reducing the volume ofthe fine droplets in mist
whose size is less than 150 run during ng the said dispersion by at least 20%. In one
embodiment, the said dispersion is characterized in having a dispersed particle size from 2 — 20
um (in another embodiment, 20-60 pm) and a concentration of the dispersed particles from 0.001
to 5 wt%, in another embodiment from about 0.001 to 0.1%, still in another ment from
about 0.01 to 1%, and yet still in another embodiment from 1 to 3%, and n said
formulation is capable of reducing the volume of the fine droplets in mist whose size is less than
150 pm during spraying the said dispersion by at least 20%. In another embodiment, the said
dispersion is characterized in having a dispersed particle size from 5 — 10 um (in yet another
embodiment, 4-40 mm) and a concentration ofthe dispersed particles from 0.001 to 5 wt%, in
another embodiment from about 0.001 to 0.1 wt%, still in r embodiment fi‘om about 0.01
to 1 wt%, and yet still in another embodiment from 1 to 3 wt%, and wherein said formulation is
capable cing the volume ofthe fine drOplets in mist whose size is less than 150 pm during
spraying the said dispersion by at least 20%. The said at least 20% reduction in volume ofthe
fine droplets in mist during spraying is ed by having the said surfactant in the formulation.
The preferred dispersion system is substantially free of
crop oils used in COC.
The dispersed particles in the dispersion system are lly vesicles 0r liposomes. The
dispersed particles may trap additives, if present, in it. However, preferably it is substantially
free of crOp oils used in COC. The size distribution ofthe dispersed les, throughout the
context, is an average number and can be bimodal or multimodal. We discovered that both the
size and amount of dispersed particles are important in spray drift control. That is the
presence of
W0 201 3/098220
dispersed particles is necessary for the dispersion system to exhibit good anti-drift ty and
the concentration of dispersed particles plays an important role in determining the fine droplets
amount during spraying. If there are too many dispersed particles, there is little or no reduction in
spray drift. If there are too few dispersed particles, lly indicated by the clarity of the
on, the anti-drift performance is also not good. Only when the number and size of dispersed
particles are properly balanced spray drift reduction is significant.
lly, spray solutions meeting the above ia are characterized by the ce of
haziness.
Throughout the context, the surfactant means a single surfactant, a blend of surfactants,
or a surfactant composition comprising a surfactant, a polymer such as guar gum or a cellulosic
derived r, diluents such as water or glycols, or other additives. An added benefit is that
certain surfactants can provide additional adjuvancy to the pesticide system.
Surfactants employable in this regard include, but are not limited to cationic or
quaternary surfactants, nonionic surfactants, amphoteric surfactants, anionic tants, and all
known surfactants in the industry including silicone surfactants, polymeric surfactants, and
fluoral surfactants. Not all surfactants in each ry are suitable and even with a suitable
surfactant, it has to meet the criteria. Non-limiting examples ofuseful surfactant according to
the present invention are: di-tallow dimethyl quaternary surfactants, preferably di-tallow
dimethyl chloride, Cl6-C22 amine ethoxylate with 2130 and its oxide and betaine, Cl6-C22
amine cthoxylatc quaternary with 2 E0, C 12-C22 dimothylaminopropyl amine and its oxide and
betaine, ClZ-C18 dimethyl amine oxide, ClZ-C18 dimethyl betaine, and C12-C18 amidoamine
ethoxylate derived from DETA (diethylenetriamine) and its oxide and betaine; preferably the
arbon chains are d from coco, tallow, soy, corn, castor, coconut, palm, canola, lard,
, or tall oil fatty acid mentioned usly.
In one embodiment, the surfactant is a nitrogen containing surfactant. The nitrogen
containing surfactant may be di-alkyl di—rnethyl quaternary surfactant with a counterion of
chloride, bromide, methylsulfate, carbonate, or bicarbonate; an alkyl
dimethylamidopropylamine; an alkyl dimethylamidopropylamine oxide or alkyl
dimethylamidopropylamine betaine; an alkyl amidoamine ethoxylate wherein the alkyl
amidoamine ethoxylate is a product derived from alkyl fatty acid and diethylenetriamine
ed by ethoxylation; an alkyl di-ethoxylated with 2E0 methyl chloride quaternary
2012/076535
surfactant. The alkyl group in the above-mentioned nitrogen containing surfactant is C 12-C22
(in one embodiment, C16-C22), saturated or non-saturated, linear or branched alkyl group
derived from oil of coco, soy, palm, castor, tallow, corn, lard, peanut or tall, including the
ized version ofthe oil.
The nitrogen containing surfactant may also be a tertiary amine surfactant ofthe formula:
wherein R1 represents a straight or branched chain (Cm-(322) alkyl and R2 and R3 independently
represent a straight or branched chain (C1—C3) alkyl. r, the nitrogen containing surfactant
may also be a tertiary amine oxide surfactant ofthe formula:
R4 I R6
l 0 '
wherein R4 is a straight or branched chain (Cm-C22) alkyl or an alkyletherpropyl, and R5 and R6
independently are ht or branched chain (Cl-ng) alkyl or ethoxylates or propoxylates of the
formula:
Zea/{CZH‘iOiBH 24C2H3(CH3)0 n H
wherein n is an r from 1 to 20. In one embodiment, the tertiary amine oxide is coco
yl amineoxide.
Furthermore, the nitrogen containing surfactant may be an alkoxylated amineoxide
derived from alkoxylated alkylamine, wherein the alkyl group is C l2—C22, saturated or non-
ted, linear or ed alkyl group derived from oil of coco, soy, palm, castor, tallow, corn,
lard, peanut or tall, including the epoxydized version ofthe oil. In one embodiment, the
alkoxylated amineoxide is an ethoxylated alkyl amineoxide with two ethoxylation units (2130).
The nitrogen containing surfactant may also be an alkoxylated amide. The alkoxylated
amide may be a reaction product of fatty acid with diethanolamine. r, the alkoxylated
amide may be ethoxylated with 2 — 20 ethoxylation units.
Alternatively, the lated amide may be a reaction product of fatty acid with
monoethanolamine, which may also be ethoxylated with 2 — 20 ethoxylation units.
Because ofthe ce of a dispersed particle phase, the spray solution lly has a
haze or turbidity in it. In other words, a clear spray solution will generally not have good drift
control property. Correlating the haziness with good drift control is a very helpful and important
tool. This discovery provides a convenient tool for farmers to judge r the drift control
agents they have added to the spray tank work or not because they can simply look at the spray
solution appearance and know the result without doing complicated experiment. This discovery
is also important for a ator who is deveIOping drift control formulations. The
presence of
ss in a spray solution is a necessary condition for a good drift control.
The 00mpositions ofthe invention can be prepared in the manner known to the skilled
artisan, including but not limited to in-can and tank mix and application ofthe final formulation
may be pre- or post-emergence. Post-emergence application results in particular advantages.
In one embodiment, the agrochemical formulation is a herbicide formulation having
improved drift control comprising the tant drift control agent in accordance with the
ion. Examples of suitable herbicides e, but are not limited to:
acctochlor, acifluorfcn, aclonifcn, alachlor, amctryn, amidosulfuron, aminopyralid,
amitrole, anilofos, asularn, atrazine, azafenidin, azimsulfuron, benazolin, benfluralin,
bensulfuron-methyl, one, bifenox, binalafos, bispyribac—sodium, bromacil, bromoxynil,
lor, butroxidim, cafenstrole, amide, carfentrazone-ethyl, chloridazon, Chlorimuron—
ethyl, chlorobromuron, chlorotoluron, chlorsulfuron, cinidon-ethyl, cinosulfuron, clethodim,
Clomazone, Clopyralid, Cloransulam-methyl, Clorsulfuron, Cyanazine, Cycloate,
Cyclosulfamuron, Cycloxydim, Dalapon, Desmedipham, Dicarnba, Dichlobenil, Dichlormid,
Diclosulam, Diflufenioan, Dimefuron, peate, achlor, Dimethenamid, ,
Diuron, Esprocarb, Ethalfluralin, Ethametsulfuron-methyl, Ethofumesate, Ethoxysulfuron,
Fentrazamide, Flazasulfuron, Florasulam, Fluchloralin, Flufenacet, Flumetsulam, Flumioxazin,
Fluometuron, Flupyrsulfuron-methyl, Flurochloridone, Fluroxypyr, Flurtamone, Fomesafen,
Foramsulfuron, Glyphosate, Glufosinate, Hexazinone, Irnazamethabenz-m, Imazamox, mazapic,
W0 201 3/098220 PCT/EPZO1 2/076535
Iinazapyr, Iinazaquin, Imazethapyr, Imazosulfiiron, Iodosulfuron, onynil, Isoproturon, Isoxaben,
Isoxaflutole, Lactofen, Lenacil, Linuron, Mefenacet, Mesosulfuron-Methyl, Mesotrione,
Metamitron, Metazachlor, Methabenzthiazuron, Metobromuron, Metolachlor, Metosulam,
Metoxuron, Metribuzin, Metsulfuron—methyl, Molinate, MSMA, Napropamide, Nicosulfuron,
Norflurazon, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxyfluorfen, Paraquat,
Pendimethalin, Phenmedipham, Picloram, Pretilachlor, Profoxydim, Prometryn, Propanil,
Propisochlor, Propoxycarbazone, Propyzamide, Prosulfocarb, Prosulfuron, Pyraflufen-ethyl,
sulfuron, Pyridate, Pyrithiobac, Quinclorac, Quinmerac, Rimsulfuron, Sethoxydim,
Simazine, S-Metolachlor, ricne, Sulfentrazone, Sulfosulfiiron, Tebuthiuron,
Tepraloxydim, Terbuthylazine, Terbutryn, Thifensulfiiron—methyl, Thiobencarb, xydim,
late, Triasulfiaron, uron-methyl, Triclopyr, Trifloxysulfuron, Trifluralin,
Triflusulfuron—methyl, Tritosulfuron, and mixtures and combinations thereof. Preferred
herbicides are Acetochlor, Atrazine, a, Glufosinate, Paraquat, and mixtures and
combinations thereof. More preferred herbicides are sate, Atrazine, Dicamba, and
Glufosinate and mixtures and combinations thereof. The most preferred herbicides are salts of
glyphosate and inate-ammonium. When the herbicide is an acid, it can be used in the acid
form, though it is preferred that the herbicide be in the salt form selected from at least one of the
group ofan amine, lithium, sodium, ammonium or potassium. It shall be pointed out that when a
pesticide s in the text as a l name without specifying the counterions, it means both
its acid form and salt form throughout the context.
In another embodiment, the agrochemical ation is a ide formulation having
improved drift control comprising the surfactant drift control agent in accordance with the
invention. Examples of suitable fungicides include, but are not limited to:
Acibenzolar-S-methyl, rph, amisulbrom, anilazine, azaconazole, azoxystrobin, benalaxyl,
benodanil, benomyl, benthiavalicarb, binapacryl, biphenyl, anol, blasticidin—S, boscalid,
bromuconazole, bupirimate, captafol, captan, carbendaziin, carboxin, carpropamid, chloroneb,
chlorothalonil, linate, copper, cyazofamid, cyflufenamid, cymoxanil, cyproconazole,
cyprodinil, dichlofluanid, diclocymet, diclomezine, dicloran, diethofencarb, difenoconazole,
diflumetorim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole, p, dithianon,
dodemorph, , phos, enestrobin, onazole, etaconazole, ethaboxam, ethirimol,
etridiazole, famoxadone, fenamidone, fenarimcl, fenbuconazole, fenfuram, fenhexamid,
fenoxanil, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin de, fentin
hydroxide, , ferimzone, am, fludioxonil, flumorph, fluopicolide, fluoxastrobin,
fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-Al, fthalide,
fuberidazole, xyl, furametpyr, guazatine, hexaconazole, hymexazole, imazalil,
imibenconazole, iminoctadine, rb, ipconazole, iprobenfos (IBP), iprodione, iprovalicarb,
isoprothiolane, isotianil, mycin, kresoxim—methyl, laminarin, mancozeb, mandipropamid,
maneb, material of biological, mepanipyrim, mepronil, meptyldinocap, metalaxyl, metalaxyl-M,
metconazole, methasulfocarb, metiram, metominostrobin, metrafenone, mineral oils, organic
oils, myclobutanil, naftifine, nuarimol, octhilinone, ofurace, origin, orysastrobin, oxadixyl,
oxolinic acid, oxpoconazole, oxycarboxin, oxytetracycline, pefi1razoate,penconazole,
uron, penthiopyrad, phophorous acid and, picoxystro bin, lin, polyoxin, potassium
bicarbonate, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb,
proquinazid, prothiocarb, prothioconazole, pyraclostrobin, pyrazophos, pyribencarb,
pyributicarb, pyrifenox, pyrimethanil, pyroquilon, quinoxyfen, quintozene (PCNB), salts,
silthiofam, nazole, spiroxamine, streptomycin, r, nazole, teclofthalam,
ene (TCNB), terbinafine, tetraconazole, ndazole, thifluzamide, thiophanate,
anate-methyl, thiram, tiadinil, tolclofosmethyl, tolylfluanid, triadimefon, triadimenol,
triazoxide, tricyclazole, tridemorph, trifloxystrobin, izole, triforine, triticonazole,
validamycin, valiphenal, Vinclozolin, zineb, ziram, and zoxamide, and mixtures and
2O combinations thereof
Still another embodiment of the present invention is an insecticide formulation having
improved drift control comprising the surfactant drift l agent in accordance with the
invention. Examples of suitable insecticides include, but are not limited to: kerosene or borax,
botanicals or natural organic nds (nicotine, pyrethrin, strychnine and rotenone),
chorinated hydrocarbon (DDT, lindane, chlordane), phosphates (malathion and diazinon),
carbamates (carbaiyl and propoxur), fumigants (naphthalene) and benzene (mothballs), synthetic
pyrethroids, and es and combinations thereof.
Yet still another embodiment ofthe present invention is a mixture of
any herbicide,
fungicide, and insecticide selected form the above groups having improved drift control
comprising the surfactant drifi control agent in accordance with the invention.
The above listings of specific surfactants and pesticides are not intended to be inclusive
of all possibilities.
The invention will now be illustrated by the following non-limiting examples.
We used Sympatec Helos-R series laser diffraction system to e the drOplets distribution
during spraying (Spray condition: 40 psi, Teejet 8002 vs. nozzle)
Samples description:
Table l. The chemicals discussed in the current patent
Description
Silwet‘fi‘ L-77 kyleneoxide Modified Heptameth ltrisiloxane
LLDDMA 50% ac. 2,4-D dimethylamine salt, a ide
Di—tallow dimethyl chloride quaternary surfactant, 75% in isoprOpyl
® 2HT—75 IPA alcohol
Di-tallow dimethyl chloride quaternary tant, 75% in propylene
Arquad® 2HT-75 PG - lycol
Ethomeen® T/12 Ethoxylated tallowamine-2EO
Etho c uad® C/12 Ethox rlated cocoamine-ZEO meth l chloride uaterna surfactant
Ethoquad® E/12 Ethoxylated erucylamine-ZEO methyl de quaternary surfactant
Armeen® APA T Tallow dimethylamidopropylamine
Ethomeen® T/20 Ethoxylated tallowamine-l OEO
Aromox® C/12 Cocoaminc oxide with 2 E0 (30%? active)
DR—ZOO Hydrox prep lmodified guar um
Example 1: Effect of the size of dispersed particles on anti—drift performance.
Pure water produces a lot of fine droplets during spraying (usually 47 ~ 50 % vol. with
size < 150 um) which is prone to drift. Adding 0.2% Silwet® L-77 to water formed a hazy
sion and this dispersion was able to reduce the fine droplets to ~24% (a ~50% reduction in
fines). This system is considered to have good anti-drift property. However, after homogenizing,
the same hazy sample turn clear and the percent fine droplets produced while spraying the clear
sample went back up to 47% (about the same level as water). (See the following table).
Table 2. The impact of vesicle size on the spray drift prOperty of Silwet L-77 solution
Vesicle Dynamic Spray Drift
Treatment ance size surface tension (vol. % < 150
PCT/EPZO] 2/076535
——_——
——_——
0.2% Silwet®
L-77 Stirred Hazy/turbid Large Low -24
0.2% sawed) Stirred then
L-77 homo enized Clear Small —-Lower 47
In this case, the volume percents ofthe dispersed Silwet® L—77 les (vesicles) in the stirred
only sample and the homogenized sample remained the same e the concentrations ofL-77
were the same. The result that a homogenized 0.2% L-77 (clear with small les) produced as
high amount of fines as water while a stirred only 0.2% L-77 (hazy with large les)
produced ~ 50% less fine droplets during spraying suggests that the particles size in a dispersion
plays a key role in determining the fine droplets amount during spraying. The result points out
that the spray solution with an anti-drift agent should be properly agitated so as not reduce the
particle size too much.
Example 2: Effect of the tration of dispersed Silwet L-77 les on anti-drift
performance.
The good rift property of a hazy 0.2% Silwet L-77 could also be lost by adding
small amount of certain additives. We observed that the large vesicles present in the stirred only
sample of 0.2% Silwet® L-77 (example 1) disappeared (system became clear) after adding small
amount (0.05%) 2,4-D DMA ae or many other additives. ln this case, adding 2,4—D DMA is
believed to modify the microstructure of the dispersed particles so as to decrease the amount of
the dispersed les to such a low concentration that the system became clear. The good anti-
drifi property of a hazy ® L-77 system lose its anti-drift property when it became clear
after adding 2,4-D DMA. The clear L-77 system produced a lot of fines droplets as water did
during spraying. Many alcohol ethoxylates with a few ethylene oxide units behaved similarly to
Silwet® L—77. We believe the dispersion of alcohol ethoxylates was also a vesicle or me
dispersion. It is showed in this example that the presence of dispersed droplets (in vesicle or
liposome form) is necessary for this dispersion system to exhibit good anti-drift property and the
concentration of particles plays an important role in determining the fine droplets amount during
spraying.
PCT/EP201 2/076535
This example trates that general conclusions about the anti-drift property of a surfactant
cannot be drawn. An anti-drift agent such as alcohol ethoxylates can loss their anti-drift property
in real ide formulations due to the disappearance of the dispersed macrostructure or the
turbidity.
Exam 1e 3: Effect of the concentration of dis ersed uaternarv surfactant articles on
anti—drift performance in DI water alone.
Various samples varying in concentration of Arquad® 2HT ned by drying Arquad®
2HT~75 IPA) in DI water were sprayed. The following table showed the impact of Arquad® 2HT
concentrations on the % volume of droplets whose size was less than 150 um. Details are shown
in the following table.
Table 3: The impact ofArquad® 2HT quaternary surfactant concentrations on the % volume of
ts whose size was less than 150 um
Percent reduction in
Arquad® 2HT volume of fine droplets <
quaternary % vol. (<150 150 pm when compared
surfactant Appearance 2150/um mm) to water
—00%—-_—20_0%
050% T_urbid_urbid=::—'-=_22" 0.25%
0.06% 738 28 39
0.03% Slightly
turbid 41
0.02% Slightly
turbid 36
0.01% Slightly 222 29
turbid 36
0 ) Clear 162 46 0
The turbidity in the dispersion was caused by the presence of the vesicle or liposome ofArquad
2HT. The results showed that, even at a low concentration of 0.01 % Arquadf“ 2HT, the system
was turbid and the spray drift control was very good with a reduction of about 36% ofthe fine
droplets. The drift control y was pretty nt between studied concentration range
between 0.01 and 1% Arquad® 2HT. No sed elongated Viscosity, which was deemed to be
PCT]EP201 2/076535
necessary as sed in literature, was apparent in this system. We also measured the size of the
sed particles by a particle size analyzer based on laser diffraction techniques. The result
showed that the patterns of the particle size distribution for this system were r at ent
concentration. The distribution mainly had two nominal peaks, one peaked at about 20 um
(much bigger peak) and the other at 200 um in size.
Exam le 4: Effect of the concentration of dis ersed articles Ar uad® 2HT on anti-drift
performance.
A milky sample, 5.0% ae 2.4—1) DMA + 5.0% ai Arquad® 2HT-75 PG, was d with
water. The fine droplets amount during spraying went through a minimum corresponding to the
haziness rance) of the sample. The result is shown in the following table.
Table 4. Effect of the concentration of dispersed particles (Arquad® 2HT) and solution
appearance on anti—drift performance of a 2,4-D herbicide system.
wt% ai of Arquad® 2HT-75PG Spray Drift vol. Comment
Milky Too many particles. Poor anti-
Still too many particles. Poor
Good antidrifi mance
0625 Good anti—drift performance
0.3125 Good antidrift performance
0.15625 : est anti-drift performance
0-078125 Good antidrifi performance
Number ofparticles getting a
little lower and the system
starts to loss anti-drift
0.0390625 slightly hazy 33 performance
Number ofparticles getting
very slightly even lower and the system lose
0.0195 hazy 37 good anti-drift mance
This example showed that Arquad® 2HT is useful as an anti-drift agent for a pesticide
(cg, 2,4-D DMA).
The dispersion is a dispersion of di-tallow dimethyl quaternary tant in 2,4-D DMA
spray solution. We believe the dispersed particles are in the form of vesicles or liposomes.
This result shows again that the amount ofvesicles is important in spray drift control. If
the number of vesicles is too many, there is no reduction is spray drift. If the number ofvesicles
is too little indicated by the clarity ofthe solution, the rift performance is also not good.
Only when the number ofvesicles is in the right place, the spray drift reduction is significant.
e 5: Di—tallow dimethyl quaternary surfactant (Arquad 2HT-75 IPA) can produce ~50%
reduction in fine drOplets (< 150 um, compare sample 1, 6, and 15) in the following table.
Table 5. The fine droplet volume (less than 150 um) and its appearance in ent spray
solution
Ethoxylated tallow Di-tallow dimethyl Spray
amine-10130 wt% nary Solution
surfactant wt% Appearance
active
—-_-—
_-—-_
27.69
.0 v: 0.5 30.91
h—l as 02 27.55
28.54
_. o 9.10 \1to 0.7 29.36
31-43
0-2 32-95
1-2 3867
m—54-81
-—-—--
———-—
’1‘: The appearance of freshly made #12 sample was Turbid and the
spray data showed only 32.95
% of the spray droplet was under 150 micron. However, it turned clear when the sample was
stored at room temperature overnight. The spray data showed the volume of
spray droplet under
150 micron was same as 2,4-D DMA alone.
The microstructures (vesicles) were ed under the light-microscopic only for the samples
showing a good drifting control property. Figure l is the microstructure ed for sample #1
in table 5.
The size of the marked particles shown in Figure l ranged from ~ 45 to ~ 2. The very small
particles couldn’t be measured accurately with the light—microscope.
The data can also be plotted in a phase diagram format (Figure 2).
SUBSTITUTE SHEET (RULE 26)
PCTfEP2012/076535
In the phase diagram, the region below the phase boundary curve was clear. In this region, there
was no reduction in fine droplets compared to water. At composition 20:70:10, the initial sample
was hazy and the % fine droplet was 33%. r, after overnight, the sample tum clear and
the % fine droplet became 50% (i.e., no reduction in fine droplets vs. water). In the region above
the phase boundary, the samples were hazy due to the presence of vesicles. However, not all
compositions in this hazy region possess the y to reduce fine droplets (e.g.,
SUBSTITUTE SHEET (RU LE 26)
2012/076535
composition 4025255). The best fine droplet ion region was found to be around
composition 60:10:30.
One of the components used in this example, en® T/20, is an alkylamine
ethoxylate which is a common nt for glyphosate which is the most popular tank mix
herbicide. As it is shown in the phase diagram, Ethomeen T/ZO itself doesn’t have drift control
property in this system. In fact, Ethomeen T/20 can disrupt the formation of the macrostructure
such as vesicle or liposome produced by many drift control surfactant systems, rendering the
surfactant useless in controlling the drift. The result showed in this example demonstrates that
Arquad ZHT is capable of controlling the drift even in the presence of alkylamine ethoxylate.
The presence of glyphosate in this example didn’t affect the spray drift result very much.
The drift reduction was only affected by the surfactant tration and composition
It is again showed that the presence of dispersed droplets (in vesicle or liposome form),
or the presence of haziness, is necessary for this system to exhibit good anti-drift property.
Exam 1e 6: The effect of Ar and 2 HT on the drift otential of 2 4-D DMA and Roundu ®
Weather Max svstems
Table 6. The effect of Arquad 2 HT on the drift potential of 2,4—D DMA and Roundup® Weather
Max systems
V01. % ion of
appearance fine droplets < l50
mm from water
It is showed that the presence of dispersed dr0p1ets (in vesicle or liposome form) is
necessary for this sion system to exhibit good anti-drift property, however, the
concentration ofthe surfactant was also critical for optimize the drift ion property.
Exam 1e 7: Effect of various surfactants and surfactant blends on dro let size durin
spraving 1% 2:4-D DMA svstem
Table 7. Individual Surfactants Effect on Spray Droplet size Distribution
(0.025% surfactant in 1% ac. 2,4-D DMA)
V01. % Reduction
(urn) 150 um from water
None clear 163.21 -5
1.0% a.e. 0.025% ai.
1.0% a.e. 0.025% a.i.
1.0% a c 0.025% a.i.
1.0% a.e. 0.025% a.i.
The data showed that individual surfactant alone was not able to reduce the amount of fine
droplets in 1% ac. 2,4-D DMA because the spray ons were clear (no dispersed particles).
Table 8. Effect of Surfactant Blend on Particle Size bution
(0.025% surfactants in 1% ac. 2,4—D DMA)
Vol. % Reduction of fine
Ratio droplets < 150 pm from
(surfl :suer)
All samples except #lwere a little hazy..
This example shows that the combination of surfactant is critical to achieve good drift control.
PCTIEP201 2/076535
Example 8:
The amount offine droplets during spraying of a d latex product (Primal® AC261
high gloss latex paint, studied concentration range 0.2% - 2.0%) was studied. The data in this
example shows that the amount ofpermanent spheres (latex particles) or presence of solid
particles does not contribute to reduction of fine droplets in a spray solution. That is, it further
demonstrated that the presence ofnon-permanent dispersed droplets such as vesicle (or
liposome) is necessary for a dispersion system to exhibit good rifi property.
Table 9. The concentration effect of Primal AC261 on the fine deduction of the spray solutions.
Spray on concentration Mean ofthe droplet (um) % Reduction of fine droplets
of Primal® AC261 < 150 pm (vol. %) from
2.0% 148.71
The data demonstrate that the necessary conditions for a spray solution to have significant fine
droplets (< 150 micron) number reduction are (1) the spray must s some turbidity, and (2)
the turbidity must come from a non-permanent sed phase comprising a surfactant in water.
Claims (16)
1. An aqueous emical spray solution comprising at least one agrochemical active and at least one nitrogen containing surfactant, wherein said spray solution comprises a dispersed phase comprising dispersed particles which have an average particle size between 1 to 100 s, wherein the concentration of said dispersed particles is from 0.001 to 5 wt%, and wherein said nitrogen containing surfactant ses a compound selected from the group ting of: (i) a di—alkyl di-methyl quaternary surfactant with a counterion of chloride, bromide, 10 methylsulfate, ate, or bicarbonate, wherein the alkyl group is Cl2—C22, saturated or non- saturated, linear or branched alkyl group d from oil of coco, soy, palm, castor, tallow, corn, lard, peanut or tall, including the epoxydized version of the oil; (ii) an alkyl dimethylamidopropylamine wherein the alkyl group is C12-C22, saturated or non—saturated, linear or ed alkyl group derived from oil of coco, soy, coconut, palm, 15 castor, tallow, corn, lard, peanut or tall, including the epoxydized version of the oil; (iii) an alkyl dimethylamidopropylamine oxide or alkyl dimethylamidopropylamine betaine wherein the alkyl group is 2, saturated or turated, linear or branched alkyl group d from oil of coco, soy, palm, castor, tallow, corn, lard, peanut or tall, including the epoxydized version of the oil; 20 (iv) an alkyl mine ethoxylate wherein the alkyl amidoamine ethoxylate is a product derived from alkyl fatty acid and diethylenetriamine followed by ethoxylation, and wherein the alkyl group is ClZ-CZZ, saturated or non-saturated, linear or branched alkyl group derived from oil of coco, soy, coconut, palm, castor, tallow, corn, lard, peanut or tall, including the epoxydized version of the oil; 25 (v) an alkyl di—ethoxylated with 2E0 methyl chloride quaternary surfactant, wherein the alkyl group is C16—C22, saturated or non—saturated, linear or branched alkyl group derived from oil of coco, soy, palm, castor, tallow, corn, lard, peanut or tall, including the epoxydized version of the oil; (vi) a tertiary amine surfactant of the formula: R1 R3 wherein R1 represents a straight or branched chain (Cu-C22) alkyl and R2 and R3 independently represent a straight or ed chain (Ci-€22) alkyl; and (Vii) an alkoxylated amide.
2. The aqueous agrochemical spray solution of claim 1, wherein the alkyl group of any one of (i), (ii), (iii) or (iv) is C16-C22.
3. The aqueous agrochemical spray solution of claim 1, wherein the alkoxylated amide of 10 (Vii) is a reaction t of fatty acid with diethanolamine or monoethanolamine, or is ethoxylated with 2 to 20 ethoxylation units.
4. An aqueous agrochemical spray solution of any one of claims 1 to 3 wherein said at least one nitrogen containing tant is capable of reducing the volume of the fine droplets in mist 15 whose size is less than 150 microns during spraying by at least 20% compared to the same s spray solution without the presence of the said nitrogen containing surfactant.
5. An aqueous agrochemical spray solution of any one of claims 1 to 4, wherein the aqueous agrochemical spray solution is hazy.
6. An aqueous agrochemical spray solution of any one of claims 1 to 5, wherein the agrochemical active is a herbicide formulation.
7. An aqueous agrochemical spray solution of claim 6, wherein the ide ation 25 comprises a salt of sate, a salt of 2,4-D, a salt of dicamba, a salt of glufosinate, or a combination and/or mixture thereof.
8. A method of reducing the spray drift of an aqueous agrochemical spray solution upon spraying with a spraying apparatus, which comprises adding at least one nitrogen containing surfactant to said aqueous agrochemical spray solution in an amount ive to form a dispersed phase comprising dispersed particles which have an average le size between 1 to 100 microns, wherein the concentration of said dispersed particles is from 0.001 to 5 Wt%, and wherein said aqueous spray on is capable of ng the volume of the fine droplets in mist whose size is less than 150 microns during spraying by at least 20% compared to the same aqueous spray solution without the presence of the said surfactant, and wherein said nitrogen containing surfactant comprises a compound selected from the group consisting of: 10 (i) a di—alkyl di-methyl quaternary surfactant with a counterion of chloride, bromide, methylsulfate, carbonate, or bicarbonate, n the alkyl group is C12—C22, saturated or non- saturated, linear or branched alkyl group derived from oil of coco, soy, palm, castor, tallow, corn, lard, peanut or tall, including the epoxydized version of the oil; (ii) an alkyl dimethylamidopropylamine wherein the alkyl group is ClZ—C22, saturated or 15 non—saturated, linear or branched alkyl group derived from oil of coco, soy, coconut, palm, castor, tallow, corn, lard, peanut or tall, including the epoxydized version of the oil; (iii) an alkyl ylamidopropylamine oxide or alkyl dimethylamidopropylamine betaine wherein the alkyl group is (312—022, saturated or non-saturated, linear or branched alkyl group derived from oil of coco, soy, palm, castor, tallow, com, lard, peanut or tall, including the 20 epoxydized version of the oil (iv) an alkyl amidoamine ethoxylate wherein the alkyl amidoamine late is a product derived from alkyl fatty acid and diethylenetriamine ed by ethoxylation, and wherein the alkyl group is 2, saturated or non-saturated, linear or branched alkyl group d from oil of coco, soy, coconut, palm, castor, tallow, corn, lard, peanut or tall, including 25 the epoxydized version of the oil (v) an alkyl di-ethoxylated with 2E0 methyl chloride quaternary surfactant, n the alkyl group is Cl6—C22, saturated or non-saturated, linear or branched alkyl group derived from oil of coco, soy, palm, castor, tallow, corn, lard, peanut or tall, including the epoxydized version of the oil; 30 (vi) a tertiary amine tant of the formula: wherein R1 represents a straight or branched chain 2) alkyl and R2 and R3 independently represent a straight or branched chain (Cl-sz) alkyl; and (Vii) an alkoxylated amide.
9. The method of claim 8, wherein the alkyl group of any one of (i), (ii), (iii) or (iv) is C16— C22.
10. The method of claim 8, wherein the alkoxylated amide of (vii) is a reaction product of 10 fatty acid with diethanolamine or monoethanolamine, or is ethoxylated with 2 to 20 ethoxylation units.
11. The method of any one of claims 8 to 10, wherein the agrochemical spray solution is a herbicide formulation.
12. The method of claim 11, wherein the herbicide formulation comprises a salt of glyphosate, a salt of 2,4—D, a salt of dicamba, a salt of glufosinate, or a combination and/or mixture thereof. 20
13. Use of a nitrogen ning surfactant in an aqueous agrochemical spray solution comprising at least one agrochemical active in an amount effective to form a dispersed phase comprising sed particles which have an average particle size between 1 to 100 microns, wherein the concentration of said dispersed particles is from 0.001 to 5 wt%, to provide an aqueous spray solution that has a reduced volume of the fine droplets in mist whose size is less 25 than 150 microns during spraying of at least 20% compared to the volume of the fine droplets in mist whose size is less than 150 microns in the same s spray solution without said surfactant, and wherein said nitrogen containing surfactant comprises a compound selected from the group consisting of: (i) a di—alkyl hyl quaternary surfactant with a counterion of chloride, bromide, sulfate, carbonate, or bicarbonate, wherein the alkyl group is C12-C22, saturated or non- saturated, linear or ed alkyl group derived from oil of coco, soy, palm, castor, tallow, corn, lard, peanut or tall, including the epoxydized version of the oil; (ii) an alkyl dimethylamidopropylamine wherein the alkyl group is C12—C22, saturated or non-saturated, linear or branched alkyl group derived from oil of coco, soy, coconut, palm, castor, tallow, corn, lard, peanut or tall, including the epoxydized n of the oil; (iii) an alkyl dimethylamidopropylamine oxide or alkyl dimethylamidopropylamine betaine wherein the alkyl group is C12—C22, saturated or non-saturated, linear or branched alkyl 10 group derived from oil of coco, soy, palm, castor, tallow, corn, lard, peanut or tall, including the epoxydized version of the oil; (iv) an alkyl amidoamine ethoxylate wherein the alkyl amidoamine ethoxylate is a product derived from alkyl fatty acid and diethylenetriamine followed by ethoxylation, and wherein the alkyl group is C12-C22, saturated or non-saturated, linear or branched alkyl group 15 derived from oil of coco, soy, coconut, palm, castor, tallow, corn, lard, peanut or tall, including the epoxydized version of the oil; (v) an alkyl di-ethoxylated with 2130 methyl chloride nary surfactant, wherein the alkyl group is C16—C22, saturated or non—saturated, linear or ed alkyl group derived from oil of coco, soy, palm, , tallow, corn, lard, peanut or tall, including the epoxydized version 20 of the oil; (vi) a tertiary amine surfactant of the formula: R1 R3 n R1 represents a straight or branched chain 2) alkyl and R2 and R3 independently represent a straight or branched chain (Cl-sz) alkyl; and 25 (vii) an alkoxylated amide.
14. The use of claim 13, wherein the alkyl group of any one of (i), (ii), (iii) or (iv) is C16- C22.
15. The use of claim 13, n the alkoxylated amide of (vii) is a reaction product of fatty acid with diethanolamine or monoethanolamine, or is ethoxylated with 2 to 20 ethoxylation units.
16. The aqueous agrochernical spray solution of claim 1, ntially as herein described with reference to any one of the Examples and/or
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161581395P | 2011-12-29 | 2011-12-29 | |
US61/581,395 | 2011-12-29 | ||
US201261648105P | 2012-05-17 | 2012-05-17 | |
US61/648,105 | 2012-05-17 | ||
PCT/EP2012/076535 WO2013098220A1 (en) | 2011-12-29 | 2012-12-21 | Macrostructure forming surfactants useful as spray drift control agents in pesticide spraying applications |
Publications (2)
Publication Number | Publication Date |
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NZ626024A NZ626024A (en) | 2016-09-30 |
NZ626024B2 true NZ626024B2 (en) | 2017-01-05 |
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