MXPA99001168A - Pesticidal compositions - Google Patents
Pesticidal compositionsInfo
- Publication number
- MXPA99001168A MXPA99001168A MXPA/A/1999/001168A MX9901168A MXPA99001168A MX PA99001168 A MXPA99001168 A MX PA99001168A MX 9901168 A MX9901168 A MX 9901168A MX PA99001168 A MXPA99001168 A MX PA99001168A
- Authority
- MX
- Mexico
- Prior art keywords
- grams
- solution
- water
- diisocyanate
- pesticide
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 71
- 230000000361 pesticidal effect Effects 0.000 title claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 121
- 239000000575 pesticide Substances 0.000 claims abstract description 32
- 239000000243 solution Substances 0.000 claims description 162
- 239000002253 acid Substances 0.000 claims description 48
- 239000004094 surface-active agent Substances 0.000 claims description 48
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 24
- 229920000642 polymer Polymers 0.000 claims description 21
- 239000002202 Polyethylene glycol Substances 0.000 claims description 20
- 230000002363 herbicidal effect Effects 0.000 claims description 20
- 239000004009 herbicide Substances 0.000 claims description 20
- 229920001223 polyethylene glycol Polymers 0.000 claims description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 19
- 150000001412 amines Chemical class 0.000 claims description 18
- -1 methylene diisocyanate-methylene diisocyanate-methylene diisocyanate methylene diisocyanate Chemical compound 0.000 claims description 18
- 239000002917 insecticide Substances 0.000 claims description 15
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 12
- 239000000417 fungicide Substances 0.000 claims description 12
- 230000000855 fungicidal effect Effects 0.000 claims description 11
- 239000004814 polyurethane Substances 0.000 claims description 10
- 150000003871 sulfonates Chemical class 0.000 claims description 10
- 150000007513 acids Chemical class 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 229920000162 poly(ureaurethane) Polymers 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 6
- 229920001477 hydrophilic polymer Polymers 0.000 claims description 6
- 229920002635 polyurethane Polymers 0.000 claims description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 150000003973 alkyl amines Chemical class 0.000 claims description 5
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- 229930195729 fatty acid Natural products 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- 150000002191 fatty alcohols Chemical class 0.000 claims description 5
- 239000003208 petroleum Substances 0.000 claims description 5
- LADXKQRVAFSPTR-UHFFFAOYSA-M sodium;2-hydroxyethanesulfonate Chemical class [Na+].OCCS([O-])(=O)=O LADXKQRVAFSPTR-UHFFFAOYSA-M 0.000 claims description 5
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 4
- 229920003226 polyurethane urea Polymers 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 3
- 241000607479 Yersinia pestis Species 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- JMGZBMRVDHKMKB-UHFFFAOYSA-L disodium;2-sulfobutanedioate Chemical compound [Na+].[Na+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O JMGZBMRVDHKMKB-UHFFFAOYSA-L 0.000 claims description 3
- 229920001519 homopolymer Polymers 0.000 claims description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002837 defoliant Substances 0.000 claims description 2
- 239000002274 desiccant Substances 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000001069 nematicidal effect Effects 0.000 claims description 2
- 239000005645 nematicide Substances 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims 5
- YTZRFUSYPGFDNC-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;2-methyloxirane;oxirane Chemical compound C1CO1.CC1CO1.CCC(CO)(CO)CO YTZRFUSYPGFDNC-UHFFFAOYSA-N 0.000 claims 2
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 claims 2
- 150000004665 fatty acids Chemical class 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 239000007788 liquid Substances 0.000 abstract description 15
- 238000002156 mixing Methods 0.000 abstract description 12
- 239000012948 isocyanate Substances 0.000 abstract description 9
- 150000002513 isocyanates Chemical class 0.000 abstract description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 abstract description 8
- 229920005862 polyol Polymers 0.000 abstract description 7
- 150000003077 polyols Chemical class 0.000 abstract description 7
- 150000002009 diols Chemical class 0.000 abstract description 6
- 239000000470 constituent Substances 0.000 abstract description 4
- 150000004072 triols Chemical class 0.000 abstract description 4
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 54
- 239000005562 Glyphosate Substances 0.000 description 49
- 229940097068 glyphosate Drugs 0.000 description 49
- 239000010408 film Substances 0.000 description 38
- 239000003517 fume Substances 0.000 description 26
- 238000009472 formulation Methods 0.000 description 22
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 22
- 239000000499 gel Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000005303 weighing Methods 0.000 description 16
- 241000196324 Embryophyta Species 0.000 description 15
- 229910052782 aluminium Inorganic materials 0.000 description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 11
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 235000019737 Animal fat Nutrition 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000005056 polyisocyanate Substances 0.000 description 8
- 229920001228 polyisocyanate Polymers 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 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 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 6
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 6
- 230000003247 decreasing effect Effects 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 244000025254 Cannabis sativa Species 0.000 description 5
- 240000005046 Urochloa mutica Species 0.000 description 5
- 230000000895 acaricidal effect Effects 0.000 description 5
- 239000000642 acaricide Substances 0.000 description 5
- 238000009825 accumulation Methods 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 239000005747 Chlorothalonil Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 229960005286 carbaryl Drugs 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Substances [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- JFRQLKNEDLLXOQ-UHFFFAOYSA-N 1,3-diisocyanato-2,4-dimethylbenzene Chemical compound CC1=CC=C(N=C=O)C(C)=C1N=C=O JFRQLKNEDLLXOQ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- UOAMTSKGCBMZTC-UHFFFAOYSA-N dicofol Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 UOAMTSKGCBMZTC-UHFFFAOYSA-N 0.000 description 3
- 231100000673 dose–response relationship Toxicity 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 239000000017 hydrogel Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- 239000005586 Nicosulfuron Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- GPGLBXMQFQQXDV-UHFFFAOYSA-N Primisulfuron Chemical compound OC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 GPGLBXMQFQQXDV-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 2
- 239000003090 pesticide formulation Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- YNWVFADWVLCOPU-MDWZMJQESA-N (1E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1/C(C(O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MDWZMJQESA-N 0.000 description 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
- PCKNFPQPGUWFHO-SXBRIOAWSA-N (Z)-flucycloxuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1)=CC=C1CO\N=C(C=1C=CC(Cl)=CC=1)\C1CC1 PCKNFPQPGUWFHO-SXBRIOAWSA-N 0.000 description 1
- IAKOZHOLGAGEJT-UHFFFAOYSA-N 1,1,1-trichloro-2,2-bis(p-methoxyphenyl)-Ethane Chemical compound C1=CC(OC)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(OC)C=C1 IAKOZHOLGAGEJT-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- PAUHLEIGHAUFAK-UHFFFAOYSA-N 1-isocyanato-1-[(1-isocyanatocyclohexyl)methyl]cyclohexane Chemical compound C1CCCCC1(N=C=O)CC1(N=C=O)CCCCC1 PAUHLEIGHAUFAK-UHFFFAOYSA-N 0.000 description 1
- KDLIYVDINLSKGR-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanatophenoxy)benzene Chemical compound C1=CC(N=C=O)=CC=C1OC1=CC=C(N=C=O)C=C1 KDLIYVDINLSKGR-UHFFFAOYSA-N 0.000 description 1
- XFNJVKMNNVCYEK-UHFFFAOYSA-N 1-naphthaleneacetamide Chemical compound C1=CC=C2C(CC(=O)N)=CC=CC2=C1 XFNJVKMNNVCYEK-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- NPNBMYIARMQHND-UHFFFAOYSA-N 2-[ethyl(phosphono)amino]acetic acid Chemical class C(C)N(CC(=O)O)P(=O)(O)O NPNBMYIARMQHND-UHFFFAOYSA-N 0.000 description 1
- SNZYOYGFWBZAQY-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;2-methyloxirane Chemical compound CC1CO1.CCC(CO)(CO)CO SNZYOYGFWBZAQY-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- PWVXXGRKLHYWKM-UHFFFAOYSA-N 5-[2-(benzenesulfonyl)ethyl]-3-[(1-methylpyrrolidin-2-yl)methyl]-1h-indole Chemical compound CN1CCCC1CC(C1=C2)=CNC1=CC=C2CCS(=O)(=O)C1=CC=CC=C1 PWVXXGRKLHYWKM-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- 239000005878 Azadirachtin Substances 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000005484 Bifenox Substances 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 239000005493 Chloridazon (aka pyrazone) Substances 0.000 description 1
- 239000005944 Chlorpyrifos Substances 0.000 description 1
- 239000005500 Clopyralid Substances 0.000 description 1
- 239000005504 Dicamba Substances 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 239000005573 Linuron Substances 0.000 description 1
- SUSRORUBZHMPCO-UHFFFAOYSA-N MC-4379 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 SUSRORUBZHMPCO-UHFFFAOYSA-N 0.000 description 1
- 239000005983 Maleic hydrazide Substances 0.000 description 1
- BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 description 1
- 239000005802 Mancozeb Substances 0.000 description 1
- 239000005583 Metribuzin Substances 0.000 description 1
- VWYHWAHYVKZKHI-UHFFFAOYSA-N N=C=O.N=C=O.C1=CC(N)=CC=C1C1=CC=C(N)C=C1 Chemical compound N=C=O.N=C=O.C1=CC(N)=CC=C1C1=CC=C(N)C=C1 VWYHWAHYVKZKHI-UHFFFAOYSA-N 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- XBXFGOSIPGWNLZ-UHFFFAOYSA-N O=C1C=C(CC(C)(C)C1)C.N=C=O Chemical compound O=C1C=C(CC(C)(C)C1)C.N=C=O XBXFGOSIPGWNLZ-UHFFFAOYSA-N 0.000 description 1
- 241000577218 Phenes Species 0.000 description 1
- 239000005595 Picloram Substances 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- HUTDUHSNJYTCAR-UHFFFAOYSA-N ancymidol Chemical compound C1=CC(OC)=CC=C1C(O)(C=1C=NC=NC=1)C1CC1 HUTDUHSNJYTCAR-UHFFFAOYSA-N 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- VEHPJKVTJQSSKL-UHFFFAOYSA-N azadirachtin Natural products O1C2(C)C(C3(C=COC3O3)O)CC3C21C1(C)C(O)C(OCC2(OC(C)=O)C(CC3OC(=O)C(C)=CC)OC(C)=O)C2C32COC(C(=O)OC)(O)C12 VEHPJKVTJQSSKL-UHFFFAOYSA-N 0.000 description 1
- FTNJWQUOZFUQQJ-NDAWSKJSSA-N azadirachtin A Chemical compound C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C\C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-NDAWSKJSSA-N 0.000 description 1
- FTNJWQUOZFUQQJ-IRYYUVNJSA-N azadirachtin A Natural products C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C/C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-IRYYUVNJSA-N 0.000 description 1
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- SFNPDDSJBGRXLW-UITAMQMPSA-N butocarboxim Chemical compound CNC(=O)O\N=C(\C)C(C)SC SFNPDDSJBGRXLW-UITAMQMPSA-N 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 1
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 1
- WEBQKRLKWNIYKK-UHFFFAOYSA-N demeton-S-methyl Chemical compound CCSCCSP(=O)(OC)OC WEBQKRLKWNIYKK-UHFFFAOYSA-N 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000013401 experimental design Methods 0.000 description 1
- 239000013020 final formulation Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- IXORZMNAPKEEDV-OBDJNFEBSA-N gibberellin A3 Chemical compound C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 IXORZMNAPKEEDV-OBDJNFEBSA-N 0.000 description 1
- 150000002332 glycine derivatives Chemical class 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000003673 groundwater Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- CONWAEURSVPLRM-UHFFFAOYSA-N lactofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CONWAEURSVPLRM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- NNKVPIKMPCQWCG-UHFFFAOYSA-N methamidophos Chemical compound COP(N)(=O)SC NNKVPIKMPCQWCG-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229940057847 polyethylene glycol 600 Drugs 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 229940079862 sodium lauryl sarcosinate Drugs 0.000 description 1
- ADWNFGORSPBALY-UHFFFAOYSA-M sodium;2-[dodecyl(methyl)amino]acetate Chemical compound [Na+].CCCCCCCCCCCCN(C)CC([O-])=O ADWNFGORSPBALY-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Abstract
A pesticidal composition including isocyanate capped high molecular weight diols, triols and polyols. A pesticide and water are combined with hydrophilic isocyanate end-capped prepolymers in order to significantly improve the efficacy of the pesticide. The liquid pesticidal compositions of the present invention can be prepared by simply mixing the various constituents. The order of addition can be used effectively to cap free isocyanate groups in the hydrophilic prepolymer.
Description
PESTICIDE COMPOSITIONS
BACKGROUND OF THE INVENTION
Glyphosate, or N-fos fonomet ilglicina
(HOOCCH2NHCHzPO (OH) L), is a well-known translocalized, postemergence, broad-spectrum herbicide. The commercially typical formulation contains about 41% of the glyphosate salt of isopropylamine and is believed to contain about 12% by weight of an ethoxylated animal fat amine surfactant. Glyphosate is a relatively insoluble acid, and is therefore formulated and typically applied as a salt, such as the sodium or ammonium salt of isopropylamine.
Surfactants are typically incorporated into the formulation to improve the activity of glyphosate. However the term "surfactant" is ambiguous, as the form supplied by the manufacturers is not necessarily a simple compound, nonetheless
REF .: 29347 can be a mixture. For example, with ethoxylated surfactants, the degree of ethoxylation can be and is typically a statistical mixture. The literature in particular describes the use of surfactants in glyphosate compositions and in particular, Weed Science, Vol. 25, pp. 275-287 (1977) demonstrated the need to include a surfactant in glyphosate formulations. Conventional glyphosate formulations include the use of surfactants such as siloxanes to improve the rain-setting properties of glyphosate formulations. However, the commercialization of glyphosate formulations has been hampered by the cost of incorporating such surfactants into the formulations, and by the hydrolytic instability of such adjuvants. Other formulations including surfactants are set forth in US Patent Nos. 5362,705, 5,180,414 and 5,118,338.
Furthermore, in view of the environmental concern surrounding the use of chemical pesticides and the possibility that residues of these could contaminate food, groundwater, etc., a substantial reduction in the amount of pesticide necessary to make it cash.
It is therefore an object of the present invention to improve the rain-setting properties of pesticide formulations without the use of siloxane surfactants.
It is another object of the present invention to improve the effectiveness of these formulations in an environmentally friendly manner.
BRIEF DESCRIPTION OF THE INVENTION
The problem of the prior art has been solved by the present invention, which relates to a pesticidal composition including diols, triols and high molecular weight polyols terminated with isocyanate. more specifically, the present invention relates to a pesticidal composition in which a pesticide is combined with prepolymers with hydrophilic isocyanate termination in order to significantly improve the effectiveness of the pesticide. A combination of surfactant, pesticide and a hydrophilic polymer or hydrophilic prepolymer consisting of isocyanate-terminated prepolymers which are substantially comprised of units of ethylene oxide, propylene oxide or butylene oxide or a combination thereof demonstrate the increased efficacy over the conventional pesticide formulations. The pesticidal compositions of the present invention also exhibit controlled release, thereby improving their effectiveness. The liquid compositions of the present invention can be prepared by simply mixing the different constituents. The order of the addition can be effectively used, if desired, to terminate the free isocyanate groups in the hydrophilic polymer. Hydrophilic prepolymers consist of isocyanate-terminated prepolymers which substantially comprise units of ethylene oxide, propylene oxide or butylene oxide or a combination thereof described in the art as hydratable or water soluble. See Braatz et al., Of US Patent Nos. 4,886,866, and 5,091,176, the disclosure of which is incorporated herein by reference. In one embodiment, the water soluble prepolymer can be covalently linked to an amino group if present in the pesticide
(such as glyphosate), or the alcohol group in the pesticide (such as dicofol (commercially sold as "Kelthane"). In another embodiment, the prepolymer may react with water to form polyurethane and polyurea urethane polymer gels prior to incorporation to the pesticide In another embodiment, the prepolymer can form a reaction product with a surfactant by means of a covalent bond between the isocyanate groups of the prep -imer and a surfactant group in the reactive substance.
BRIEF DESCRIPTION OF THE DRAWINGS
Figure 1 is a graph comparing the response dose of the formulations of the present invention with the commercial grade Round-up® herbicide after 28 days;
Figure 2 is a graph comparing the response dose of the formulations of the present invention with the commercial grade Round-up® herbicide after 42 days;
Figure 3 is a graph comparing the fresh weight of Scottish grass shoots after the application of the formulations of the present invention with the commercial grade Round-up® herbicide after 70 days;
DETAILED DESCRIPTION OF THE INVENTION
The term "pesticide" or "economic poison" as used herein means any substance or mixture of substances intended to prevent, destroy, repel or mitigate any insect, rodent, nematode, fungi, or weed, or any other declared life form. as a plague; and any substance or mixture of substances intended for use as regulators of the plant, defoliants, or desiccants. Suitable herbicides that can be used in the present invention, alone or in combination, include (acids, esters, salts) of phenoxy acids, benzoic acid, (acids, esters, salts) of aryloxy phenoxypropionate,
(acids, esters) of sulfonyl ureas, imidazilinones, bipyridyl, (acids, salts) of diphenyl ether, salts and esters of 2,4-D cyclohexanedione, me tanarsonate, triazines, aliphatic carboxylic acids, lactofen, linuron, glyphosate, paraquat, bifenox, benzoni trilo, carbamate, thiocarbamate, PYRAZONE, GLUFOSINATO, DESMEDIFAM, TRICLORPYR, CLOPYRALID, QUINCLORAC, ETIOZINN, PICLORAM, BENTAZON, AMITROLE, ATRIZINE, METRIBUZIN, FENMEDIFAM, CLORMETQTJAT, UNICONALOLE, PRIMI SULFURON, BROMOXINIL and the like.
Suitable insecticides and nematocides include alpha-cypermitrin, azadirachtin, butocarboxim, diazinon, demeton-s-methyl, forats, cycloprate, propargite and the like.
Suitable fungicides include triabendazole, captan, chlorothalonil, copper salts, mancozeb, procymidone, triforin, tubeconazole and the like.
Suitable acarocides include tetradifon, pyridiben, methamidophos, flucycloxuron and the like.
Regulators for the growth of suitable plants include maleic hydrazide, gibberelic acid, uniconazole, chlormequat chloride, naphthalene acetamide, ancymidol, ethylozate and the like.
Those skilled in the art will recognize that several pesticides could be used in combination, depending on the desired effects.
Suitable surfactants or spray agents are those conventional in the art, as described in US Patent No. 3,853,530, the disclosure of which is incorporated herein by reference. Such surfactants include alkylbenzene and alkylnaphthalene sulfonates, polyoxyethylene alkylphenol, sulphated fatty alcohols, acid amines or amides, sodium isethionate esters of long chain acids, sodium sulfosuccinate esters, petroleum sulfonates of sulfonated fatty acid esters, N-amino acids. -acyl such as sarcocinates, alkyl polyglycosides, alkylethoxylated amines such as the ethoxylated animal fat amine, and the like. The surfactants could include additives such as glycols including polyethylene glycol, diethylene glycol, ethylene glycol, alcohols such as methanol, ethanol, 2-propanol, n-propanol, butanol, hexanol, heptanol and the siloxanes, etc. and mixtures of the aforementioned additives.
The prepolymers used as an initial material in the pressing invention provide hydrated polyurethane, polyurea urethane and polyurea polymer gels. Several polyurethane polymers have been previously identified. Several hydrogel polymers, prepared from various prepolymers, have been prepared and used for a wide variety of applications. Typically, hydrogels are formed by polyaerizing a hydrophilic monomer in an aqueous solution under conditions such that the prepolymer begins to coalesce, forming a three dimensional polymer network, which forms a gel in the solution in concentrated form. Polyurethane hydrogels are formed by polymerization of isocyanate-terminated prepolymers to create urea and urethane linkages. More specifically, the prepolymers are prepared from solutions of prepolymers terminated with high molecular weight isocyanate substantially or exclusively comprised of oxide units. ethylene, propylene oxide or butylene oxide or mixtures thereof. Preferably the prepolymers are derivatives of the polymer units of monomers (the prepolymer units) of at least 75% of which are oxyethylene-based diols or polyols having molecular weights of from about 100 to about 30,000, preferably 7,000 to 30,000, with essentially all the hydroxyl groups of these diols or polyols terminated with polyisocyanate. Suitable polyols include triols such as glycerol, trimethylolpropane, trimethylolethane and triethanolamine. The prepolymers useful in the invention are prepared by reacting selected diols, triols or polyols with polyisocyanate in an isocyanate to hydroxyl ratio of about 1.8 to about 2.2 so that essentially all of the hydroxyl groups are terminated with polyisocyanate. Aromatic, aliphatic or cycloaliphatic polyisocyanates could be used. The use of aliphatic polyisocyanates allows a greater degree of workability and / or ordering since the aliphatic isocyanate-terminated prepolymers typically require approximately 20 to 90 minutes to pass from the gel to the hydrated polymer state. Prepolymers terminated with aromatic polyisocyanates form gels more rapidly, in about 30 to 60 seconds. The aliphatic polyisocyanates are also preferred in view of the decreased toxicological considerations. Examples of di- and polyfunctional isocyanates are as follows: toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, commercial mixtures of toluene-2, 4 and 2,6-diisocyanate, iso-fordoisocyanate, ethylene diisocyanate, eylidene-diisocyanate , propylene-1, 2-diisocyanate, cyclohexylene-1,2-diisocyanate, cyclohexylene-1,4-diisocyanate, m-phenylene diisocyanate, 3, 3"-diphenyl-4, 4" -biphenylene diisocyanate, 1, 6 hexamethylene diisocyanate, 1,4-tetramethylene diisocyanate, 1, 10-decamethylene diisocyanate, cumen-2,4-diisocyanate, 1,5-naphthalene diisocyanate, methylene dicyclohexyl diisocyanate, 1,4-cyclohexylene diisocyanate, p-tetramethyl xylene diisocyanate, p phenylene diisocyanate, 4-methoxy-l, 3-phenylene diisocyanate, 4-chloro-l, 3-phenylene diisocyanate, 4-bromo-l, 3-phenylene diisocyanate, 4-ethoxy-l, 3-phenylene. diisocyanate, 2,4-dimethyl-1,3-phenylene diisocyanate, 2,4-dimethyl-1,3-phenylene diisocyanate, 5,6-dimethylisocyanate, 2,4-dimethyl-1, 3-phenylene diisocyanate, , 6-dimethyl-1,3-phenylene diisocyanate, 2,4-diisocyanate diphenylether, 4,4'-diisocyanatodiphenylether, benzidine diisocyanate, 4, β-dimethyl-1,3-phenylene diisocyanate, 9, 10-anthracene diisocyanate, 4 , 4'-diisocyanate dibenzyl, 3,3 '-dimethyl-4,4'-diisocyanatodiphenyl ethane, 2, β-dimethyl-4, 4'-diisocyanatodi phene, 2,4-di isocyanates, thiobenzene, 3,3' -dimethoxy-4,4'-diisocyanatodiphenyl, 1, 4, -antracendiisocyanate, 2, 5-fluorendiisocyanate, 1,8-naphthalene diisocyanate, 2, β-diisocyanatobenzfuran, 2,4,6-toluene triisocyanate, p, p ', p "-trifenilme tan triisocyanate, trifunctional trimer
(isocyanurate) of isophorone diisocyanate, trifunctional biuret of hexamethylene diisocyanate, trifunctional trifunctional (isocyanurate) of hexamethylene diisocyanate, 4,4 '-difenylmethane polymeric diisocyanate, xylylene diisocyanate and methyl ether xylylene diisocyanate.
The finishing of the diols or polyols with polyisocyanates to form prepolymers for use in the present invention is effected using stoichiometric amounts of surfactants. The ratio of the isocyanate group to hydroxyl should be between about 0.01 and about 10, preferably 0.1 to 3, more preferably 0.2 to 2.2. Larger ratios could be used but are not preferred since they could cause problems associated with excessive amount of monomer present in the final products. The termination reaction could be by any convenient method or procedure, such as about 20: to about 150"* C, under dry nitrogen, for about 2 hours to about 14 days, preferably in the absence of catalyst. ° at 100 ° C. The reaction is terminated when the isocyanate concentration approaches the theoretical values.
Preferred polymers include toluene diisocyanate polyethylene glycol tri ethylolpropane, homopolymer of methylene diisocyanate-methylene diisocyanate methylene diisocyanate polyethylene glycol polymer, toluene diisocyanate and polymer of ethylene oxide and propylene oxide with trimethylolpropane, isophorone isocyanate and ethylene oxide polymer of propylene oxide - trimethylolpropane, toluene diisocyanate polyethylene glycol trilactate, and polyethylene glycol terminated with toluene diisocyanate. These prepolymers are available under the registered name of HIPOL® from Hampshire Chemical Corp., and include HIPOL® PreMA®, HIPOL® 2000, HIPOL® 3000, HIPOL® 4000, HIPOL® 5000, and HIPOL® biodegradable.
Typically the ratio of pesticide to prepolymer is from about 0.001 to about 10.
In the case of glyphsate, for example, the neutralization of the glyphosate acid to form a herbicidally active glyphosate derivative can be effected with any suitable base, which includes metal alkali, rare earth alkali and ammonium hydroxides and alkylamines. Preferably glyphosate salts on neutralization include the N-phos fonomethalglycine salt of mono (trimethylamine), N-fos fonomet il glycine salt of mono (diethylamine), N-fos salt, monoisopropylamine fonomethylglycine salt, N-fos salt fonomet iliglicina of mono-n-propylamine, N-phosphono ethylglycine salt of mono (animal fat amine), monosodium salt of N-phosphonomethylglycine and the monopotassium salt of N-phosphonomethylglycine. Those skilled in the art will readily appreciate that the corresponding salts of di- and tri- N-fos fonomethylglycine can also be prepared by increasing the amount of the base accordingly added.
In the first embodiment of the present invention, the prepolymer can be incorporated into the solution as a reaction product with water. The amount of prepolymer used should be quite low in order to avoid gel formation immediately. Generally less than about 20% by weight, more preferably about 2 to 10% by weight, and more preferably about 3 to 7% by weight are suitable. If larger prepolymer amounts are desired, primary or secondary alkyl amine can be added to help prevent gel formation. Preferably the reaction is carried out from about the freezing point of the water to room temperature. The highest temperature can be used, although this improves the speed of gel formation. The pesticide is added after the prepolymer / water reaction is complete. The amount of pesticide used will depend on the amount desired in the final formulation, and can generally vary from about 0.1% to about 80% by weight. A clear and stable solution or suspension is obtained. In the case of glyphosate, the current commercial formulation employs approximately 36% glyphosate acid (41% as the isopropylamine salt). The addition of glyphosate acid causes the formation of a white suspension. The suspension is neutralized with a suitable base, preferably a hydroxide such as sodium, potassium or ammonium hydroxide, more preferably isopropylamine. Sufficient base is preferably added to form the monosal, although di- and tri-salts can also be formed with the addition of the base.
Surfactant may be added at any point after the reaction of the prepolymer with water, for example, immediately before the addition of pesticide, immediately before neutralization, or after neutralization. Preferably the amount of surfactant added is from about 0.1 to about 20% (w / w) of pesticide, with the actual amounts depending on the identification of the surfactant used. With the evaporation of water, strong elastic films are obtained. These films are water-insoluble hydratable films which after spray application of the formulation to the substrate. These hydratable films are desirable since they minimize or prevent the pesticide from being removed from the surface of the substrate being sprayed (such as a plant leaf). These hydratable films also greatly improve the fixation with the rain formulation.
In the second embodiment of the present invention, applicable to pesticides having a surfactant group capable of forming a covalent bond with the prepolymer, the prepolymer is incorporated into the formulation as a reaction product covalently linked with the pesticide. Specifically, in the case of glyphosate, the glyphosate acid is added directly to the prepolymer, and reacts with the free isocyanate groups present in the prepolymer to terminate it. Partial or complete termination with the isocyanate groups may be obtained, depending on the relative amount of glyphosate used. The resulting reaction product is neutralized with a suitable base as in the first embodiment. Surfactants may be added before or after neutralization. The amounts of the constituents used are similar to those set forth above with respect to the first embodiment.
In the third embodiment of the present invention, the isocyanate-terminated hydrophilic prepolymers are incorporated as a reaction product with a surfactant by means of a covalent bond between the isocyanate groups (-NCO) of the polymer and the surfactant groups typically available in the surfactants, such as the primary or secondary reactive amine groups (-NH, -NH2), the sulfhydryl groups (-SH), the hydroxyl groups (-OH) and the carboxylate groups "(-COOH)." As in the second In the embodiment, the one with the isocyanate groups in the prepolymer may be partial, or complete, depending on the relative amounts of surfactants used.
Preferably the surfactant is an ethoxylated alkylamine which may include alkyl or alkylarylethoxylates, which include a mixture of polyethylene glycol, diethylene glycol and ethylene glycol. Then the pesticide is added. In some cases suitable cationic or anionic surfactants can be used. The amounts of constituents used are similar to those discussed above with respect to the first embodiment.
The formulations of the present invention are preferably applied by spraying on the soil portions of the plants. The concentration of the active ingredient must be present in effective amounts of pesticide, which depend on the particular pesticide and the desired response.
EXAMPLE 1
28 grams of hydrophilic prepolymer HYPOL® PreMA® G-50 were added at room temperature to 972 grams of water. The solution was stirred for two hours to ensure complete reaction of the prepolymer with the water. 100 grams of glyphosate acid were added, and the pH was adjusted to 4.8 with isopropylamine. A clear solution was obtained.
Approximately 25% of the solution was allowed to dry on a fume hood overnight. A strong elastic film was obtained.
A part of the solution was diluted with approximately 1% glyphosate acid equivalent to 50 ml. of water and was also allowed to dry in a fume hood all night. A strong elastic film was obtained.
EXAMPLE 2
grams of hydrophilic prepolymer HYPOL® PreMA® G-50 was added at room temperature to a mixture of ethoxylated alkylamine (62.5 g) and water (907.5 g). The solution was stirred for two hours. 150 grams of glyphosate acid were added, and neutralized with isopropylamine at pH 4.8. A clear, stable solution was obtained.
Approximately 25% of the solution was allowed to dry in a fume hood overnight. A strong elastic film was obtained.
A part of the solution was diluted with approximately 1% glyphosate acid equivalent to 50 ml. of water and was also allowed to dry in a fume hood all night. A strong elastic film was obtained.
EXAMPLE 3
42 grams of a surfactant comprising approximately 50% ethoxylated animal fat amine (15 moles ethoxylated), 20% polyethylene glycol (600 molecular weight) and 30% ethylene and diethylene glycol with 928 grams of water were mixed at room temperature. . 30 grams of hydrophilic prepolymer HYPOL® PreMA® G-50 was added to the mixture and allowed to mix for two hours. 150 grams of glyphosate acid were added and the pH was adjusted with isopropylamine to 4.8. A clear, stable solution was obtained.
Approximately 25% of the solution was allowed to dry in a fume hood overnight. A strong elastic film was obtained.
A portion of the solution was diluted with approximately 1% glyphosate acid equivalent to 50 ml. of water and was also allowed to dry in a fume hood all night. A strong elastic film was obtained.
EXAMPLE 4
62.5 grams of a surfactant comprising approximately 50% ethoxylated animal fat amine (15 moles ethoxylated), 20% polyethylene glycol (600 molecular weight) and 30% ethylene and diethylene glycol were mixed at room temperature with 877.5 grams of Water. 60 grams of HYPOL® PreMA® G-50 were added to the mixture and stirring was allowed for three hours. 150 grams of glyphosate acid were mixed in the resulting solution. The suspension was neutralized with isopropylamine at pH 4.8. A clear, stable solution was obtained.
Approximately 25% of the solution was allowed to dry in a fume hood overnight. A strong elastic film was obtained.
A part of the solution was diluted with approximately 1% glyphosate acid equivalent to 50 ml. of water and was also allowed to dry in a 'fume hood all night. A strong elastic film was obtained
EXAMPLE 5
42 grams of a surfactant comprising approximately 50% ethoxylated animal fat amine (15 moles ethoxylated), 20% polyethylene glycol (600 molecular weight) and 30% ethylene and diethylene glycol with 897.5 grams of water were mixed at room temperature. . 60 grams of HYPOL® PreMA® were added
G-50 was added to the mixture and the solution was stirred for two hours, then 150 grams of glyphosate acid were added and the suspension was neutralized to pH 4.8 with isopropylamine.A clear, stable solution was obtained.
Approximately 25% of the solution was allowed to dry in a fume hood overnight. A strong elastic film was obtained.
A portion of the solution was diluted with approximately 1% glyphosate acid equivalent to 50 ml. of water and was also allowed to dry in a fume hood all night. A strong elastic film was obtained.
EXAMPLE 6
28 grams of hydrophilic prepolymer HYPOL® PreMA® G-50 were added at room temperature to 972 grams of water. The mixture was allowed to stir for 3 hours. 100 grams of glyphosate acid were added, and the pH was adjusted to 4.8 with isopropylamine. A clear solution was obtained.
Approximately 25% of the solution was allowed to dry in a fume hood overnight. A strong elastic film was obtained.
A portion of the solution was diluted with approximately 1% glyphosate acid equivalent to 50 ml. of water and was also allowed to dry in a fume hood all night. A strong elastic film was obtained.
EXAMPLE 7
grams of hydrophilic prepolymer HYPOL® PreMA® G-50 were added at room temperature to 907.5 grams of water. The solution was allowed to stir for 60 minutes. 150 grams of glyphosate acid were added, followed by 62.5 grams of Toximal TA-15 surfactant. The pH was adjusted from 2.85 to 4.1 with isopropylamine. A clear solution was obtained.
Approximately 25% of the solution was allowed to dry in a fume hood overnight. A strong elastic film was obtained.
A. portion of the solution was diluted with approximately 1% glyphosate acid equivalent to 50 ml. of water and was also allowed to dry in a fume hood all night. A strong elastic film was obtained.
EXAMPLE 8
60 grams of hydrophilic prepolymer HYPOL® PreMA® were added at room temperature.
G-50 to 870 grams of water. The solution was allowed to stir for 60 minutes. 150 grams of glyphosate acid were added, followed by 62.5 grams of Toximal TA-15 surfactant. The pH was adjusted to 3.85 with isopropylamine. A clear, stable solution was obtained.
Approximately 25% of the solution was allowed to dry in a fume hood overnight. A strong elastic film was obtained.
A portion of the solution was diluted with approximately 1% glyphosate acid equivalent to 50 ml. of water and was also allowed to dry in a fume hood all night. A strong elastic film was obtained.
EXAMPLE 9
grams of glyphosate acid in 90 grams of water were stirred at room temperature. 3 grams of HYPOL® PreMA® G-50 were added and allowed to mix for 1 hour. Then, 6 grams of Toximal TA-15 surfactant were added and the contents were neutralized to a pH of 4.0 with isopropylamine. A clear, stable solution was obtained.
Approximately 25% of the solution was allowed to dry in a fume hood overnight. A strong elastic film was obtained.
A portion of the solution was diluted with approximately 1% glyphosate acid equivalent to 50 ml. of water and was also allowed to dry in a fume hood all night. A strong elastic film was obtained.
EXAMPLE 10
grams of glyphosate acid in 85 grams of water were stirred at room temperature. Three grams of hydrophilic prepolymer HYPOL® PreMA® G-50 were added and allowed to mix by
61 minutes Then 6 grams of Toximal TA-15 surfactant were added and the contents were neutralized to a pH of 4.7 with isopropylamine. A clear, stable solution was obtained.
Approximately 25% of the solution was allowed to dry in a fume hood overnight. A strong elastic film was obtained.
A portion of the solution was diluted with approximately 1% glyphosate acid equivalent to 50 ml. of water and was also allowed to dry in a fume hood all night. A strong elastic film was obtained.
EXAMPLE 11
36 grams of glyphosate acid in 69 grams of water were stirred at room temperature. 3.3 grams of hydrophilic prepolymer HYPOL® PreMA® G-50 were added to this suspension and allowed to mix for 65 minutes. Then, 6 grams of Toximal TA-15 surfactant were added and the contents were neutralized to a pH of 5 with isopropylamine. A clear, stable solution was obtained.
Approximately 25% of the solution was allowed to dry in a fume hood overnight. A strong elastic film was obtained.
A portion of the solution was diluted with approximately 1% glyphosate acid equivalent to 50 ml. of water and was also allowed to dry in a fume hood all night. A strong elastic film was obtained.
EXAMPLE 12
62.5 grams of a surfactant comprising approximately 50% ethoxylated animal fat amine (15 moles ethoxylated), 20% polyethylene glycol (600 molecular weight) and 30% ethylene and diethylene glycol were stirred at room temperature at room temperature. grams of water 60 grams of hydrophilic prepolymer HYPOL® PreMA® G-50 was added to this mixture and the contents allowed to mix for 47 minutes. Then 109.6 grams of glyphosate acid were added and the contents neutralized to pH 4.75 with isopropylamine. A clear, stable solution was obtained.
Approximately 25% of the solution was allowed to dry in a fume hood overnight. A strong elastic film was obtained.
A portion of the solution was diluted with approximately 1% glyphosate acid equivalent to 50 ml. of water and was also allowed to dry in a fume hood all night. A strong elastic film was obtained.
EXAMPLE 13
At room temperature, 30 grams of hydrophilic prepolymer HYPOL® PreMA® G-50 was mixed for 47 minutes with 907.5 grams of water. Then 42 grams of a surfactant comprising approximately 50% ethoxylated animal fat amine (15 moles ethoxylate), 20% polyethylene glycol (600 molecular weight) and 30% ethylene and diethylene glycol were added and the solution was mixed by others. 45 minutes. 109.6 grams of glyphosate acid were added, and the contents neutralized to pH 4.64 with isopropylamine. A clear, stable solution was obtained.
Approximately 25% of the solution was allowed to dry in a fume hood overnight. A strong elastic film was obtained.
A portion of the solution was diluted with approximately 1% glyphosate acid equivalent to 50 ml. of water and was also allowed to dry in a smoke hood all night. A strong elastic film was obtained.
EXAMPLE 14
A study of the dose response during the summer / fall months was performed to evaluate the efficacy of the present invention, and the results are shown in Figures 1 and 2. The experimental design was a completely randomized block with four replicates. Damage to the plant was assessed visually each week during the study.
The Scottish grass was sprayed with the formulations of Examples 2, 3 and 4, as well as the commercial grade Round up®, at 0.375, 0.75 and 1.5 pounds of active ingredient per acre. The commercial Round up® effectively controlled the Scottish grass in the two largest application rates, all the formulations shown in Figures 1 and 2 showed a high degree of damage to the Scottish grass. The fresh weight data from the shoots confirmed the damage rates. The formulations of the present invention were more effective in reducing more the weight of the Scottish grass shoots than the commercial Round up® when applied at 0.375 lb / acre, and were visually equivalent to the Round up® herbicide in the two highest concentrations .
EXAMPLE 15
A simulated rain precipitation was applied in 15 minutes, 1 hour, 3 hours, 6 hours and 24 hours after application of the formulation, and the results are shown in Figure 3. The formulations of Examples 2, 3 and 4 of the present invention significantly did not develop well as the commercial herbicide Round up®
EXAMPLE 16
The samples of Examples 2, 3 and 4 above were sprayed in a tropical environment to test the efficacy in humid and heat conditions. The samples were sprayed on parcels of 2 meters x 20 meters, with a buffer zone of 1 meter in the plot maintained between plots. The plots were marked with ropes and stakes.
The variety of the seed in the plots was noted before the application and was defined as follows:
-40% broadleaf 58-68% pastures 2% evasive sign
Climatic conditions during spray application were noted as follows:
'Temperature: 30"C Humidity: 75% Full sun in numbered plots Light wind at zero Small variation in weather after two hours of spraying time
A sprayer with a motorized pump Solo (pressurized with air) was used to spray the plots. A fan nozzle 564 was recorded and walking at a speed of 40 meters / minutes. The pressure in the tank was 2Kg.
Duplicate samples were tested for both the dose response and the fixation properties with rain. Parcels were observed after 3 weeks, and all weeks were completed until death. The response of the dose and the results of fixation with the rain are as follows in a 3-month interval.
TABLE 1
DOSE RESPONSE
SAMPLE PROPORTION VISUALIZATIONS / (1 / hectare) REMEMBERING MALE
Example 2 4.5 60-70% of broadleaf plants died. No grass was reborn, 85-98% died
Example 3 4.5 Approximately 50-60% of broadleaf plants died. No grass was reborn 95-98% died
Example 4 4.5 Some broad-leaved plants remained, 94-95% died, 5-6% were reborn. The grass was not reborn, 100% died SPARK® 70% of the broadleaf plants were reborn, 30 a; they died, 25-35¡ of the pastures were reborn ROUND UPC 4.5 Almost all the seeds were reborn TABLE 2
Fixing with the rain
SAMPLE PROPORTION TIME OF REVISIONS (1 / hectare) ADDITION OF WATER AFTER
FROM SPRAYING
Example 2 4.5 1.5 hours Something of rebirth
E j emplo3 4.5 1.5 hours No grass was reborn; some broadleaf plants were reborn
Example 4 4.5 5 hours Only two broadleaf plants were found in the plot. No grass was found. Essentially there was complete death The plots with water were also observed after 3 weeks of spraying. The pastures in the plot were only yellow and did not go brown or died.
At the end of the 6 weeks, all the weeds in all the plots died. At 6-7 months, preliminary data indicated that the plots sprayed with samples of Examples 2, 3 and 4 were still exhibiting herbicidal activity and low sapling was observed.
EXAMPLE 17
In another plot, the sample of Example 4 was sprayed. The plot was divided in half, with the second part only adding water to 1.5 hours after spraying at a rate of approximately 10 liter of water / hectare to simulate the fall of rain. After 6 weeks, all the weeds in both plots died. At 3 months, on both sides of the plot they died equally. No difference was observed between the side with water and without water.
EXAMPLE 18
Two grams of HYPOL ® 2000 prepolymer were added to 95 g of water. The solution was stirred for 5 minutes. Then two grams of sodium lauryl sarcosinate were added to the solution. Twenty grams of glyphosate acid were added and the solution was neutralized with isopropylamine to a pH of about 4.8. A clear colorless solution was obtained which exhibited some viscosity.
EXAMPLE 19
grams of glyphosate acid in 98 grams of water were added. After 30 minutes of stirring, 2 grams of HYPOL® 2000 prepolymer were added. The solution was then neutralized with 10% w / w sodium hydroxide to a pH of 4.3. A stable, clear solution that was very liquid was formed, which indicated the compatibility of the compounds.
EXAMPLE 20
Three grams of hydrophilic prepolymer HYPOL® PreMA® G-50 was added to 97 grams of water and the solution was uniformly heated from 27 ° C to 46 for 30 minutes. The solution thickened but did not gel. The contents were shaken on a cold magnetic stir plate for another 34 minutes. At 36 C, 5 grams of glyphosate acid were added and the contents were neutralized with isopropylamine at a pH of 4.6.
The contents were divided in half, with one half stored while one was retained and the other was dried in a fume hood for 5 hours. A hard and thin film was formed which was rehydrated, with the addition of water, to form a thick non-soluble film. The contents were coated and allowed to remain at room temperature overnight. The movie did not dissolve again.
EXAMPLE 21
Eight grams of Toximal TA-15 surfactant were dissolved in water for a period of 1 hour. 2.8 grams of hydrophilic prepolymer HYPOL® PreMA® G-50 was added to the solution and allowed to mix for 180 minutes. 20 grams of glyphosate acid were added and the solution was neutralized with isopropylamine from a pH of 1.96 to 4.21. A clear, stable solution with a brown color (imparted by the surfactant) was obtained.
EXAMPLE 22
Thirty-six grams of glyphosate acid were added to 69 grams of water. then 3.3 grams of hydrophilic prepolymer HYPOL® PreMA® G-50 was added to the solution and the solution was allowed to stir for 180 minutes. The solution was neutralized with isopropylamine at pH 5.00. The solution seemed slightly cloudy but did not separate, indicating that all the components in this concentration are compatible..
EXAMPLE 23
125 grams 50% of ethoxylated animal fat amine (15 equivalents of ethoxy), 20% polyethylene glycol 600, and 30% diethyl glycol / ethylene were added to 1814.0 grams of water. 120 grams of HYPOL® PreMA® G-50 hydrophilic prepolymer were added to the solution and the solution was allowed to stir for 58 minutes. Then 219.2 grams of glyphosate acid were added and the pH neutralized to 4.79 with isopropylamine. The temperature was recorded at 34"C at this point, a clear and stable solution was obtained.
EXAMPLE 24
At room temperature, 3 grams of hydrophilic prepolymer HYPOL® PreMA® G-50 were dissolved in 100 grams of water. Then one gram of this solution was mixed with 100 grams of water, and 0.89 grams of "Home Orchard Spray", a commercially available fungicide / insecticide comprised of 14% Captain, 7.5% Malation and 15% Methoxychlor, was added to this mixture. It was continued mixing until all the solids had dissolved or dispersed. The resulting concentration is equivalent to the concentration recommended for commercial use of this product.
The solution showed no signs of accumulation after mixing until after 24 hours. This is consistent with a control solution using the "Home Orcherd Spray" and water at the recommended concentration.
EXAMPLE 25
At room temperature, 3 grams of hydrophilic prepolymer HYPOL® PreMA® G-50 were dissolved in 100 grams of water. Then 3.55 grams of this solution was mixed with 100 grams of water, and 3.5 grams of "Funginex", a commercially available fungicide containing 6.5% Triforin, was added to the mixture. The solution was mixed until all the fungicide dissolved. The resulting concentration is equivalent to the concentration recommended for commercial use of this product.
The solution showed no signs of accumulation after mixing until after 24 hours. This is consistent with a control solution using only the fungicide and water at the recommended concentration.
EXAMPLE 26
At room temperature, 3 grams of hydrophilic prepolymer HYPOL® PreMA® G-50 were dissolved in 100 grams of water. Then 3.55 grams of this solution was mixed with 100 grams of water, and 0.5 grams of "Sevin", a commercially available insecticide containing 21.3% Carbaril, was added to this mixture. The solution was mixed until all the insecticide dissolved. The resulting concentration is equivalent to the concentration recommended for commercial use of this product.
The solution showed no signs of accumulation after mixing until after 24 hours. This is consistent with a control solution using only the fungicide and water at the recommended concentration.
EXAMPLE 27
At room temperature, 3 grams of hydrophilic prepolymer HYPOL® PreMA® G-50 were dissolved in 100 grams of water. Then 3.55 grams of this solution was mixed with 100 grams of water, and 0.5 grams of "Daconil", a commercially available fungicide containing 29.6% Chlorothalonil, was added to this mixture. The solution was mixed until all the insecticide dissolved. The resulting concentration is equivalent to the concentration recommended for commercial use of this product.
The solution showed no signs of accumulation after mixing until after 24 hours. This is consistent with a control solution using only the fungicide and water at the recommended concentration.
EXAMPLE 28
At room temperature, 3 grams of hydrophilic prepolymer HYPOL® PreMA® G-50 were dissolved in 100 grams of water. Then 3.55 grams of this solution was mixed with 100 grams of water, and 0.5 grams of "Bonidel", a commercially available insecticide containing 12.6% Chlorpyrifos, was added to this mixture. The solution was mixed until all the insecticide dissolved. The resulting concentration is equivalent to the concentration recommended for commercial use of this product.
The solution showed no signs of accumulation after mixing until after 24 hours.
This is consistent with a control solution using only the fungicide and water at the recommended concentration.
EXAMPLE 29
At room temperature, 4 grams of hydrophilic prepolymer HYPOL® PreMA® G-50 were dissolved in 50 grams of Option II a liquid herbicide. This solution showed no signs of settling or gel formation due to the presence of the prepolymer in the solution. After five grams of this mixture were added to 195 grams of water, a milky solution resulted.
No solution showed signs of settlement after mixing. The properties of the diluted solution were consistent with a control solution prepared using only Option II and water.
EXAMPLE 30
0.3 grams of hydrophilic prepolymer HYPOL® PreMA® G-50 was dissolved at room temperature in 100 grams of water. Four grams of Nicosulfuron, an insecticide, was added to the prepolymer and the aqueous solution and mixed until the insecticide dissolved. The properties of this solution were consistent with a control solution prepared using only the insecticide and water, indicating compatibility with the prepolymer.
EXAMPLE 31
0.9 grams of hydrophilic prepolymer HYPOL® PreMA® G-50 was dissolved at room temperature in 300 grams of water. One gram of Nicosul furon, an acaricide, was added to the prepolymer and the aqueous solution and mixed until the acaricide was dissolved. The properties of this solution were consistent with a control solution prepared using only acaricide and water, indicating compatibility with the prepolymer.
EXAMPLE 32
At room temperature, 0.6 grams of hydrophilic prepolymer HYPOL® PreMA® G-50 was dissolved in 200 grams of water. 0.5 grams of Primisulfuron, a herbicide, was mixed, mixed with the 200 grams of prepolymer and the aqueous solution. The solution was mixed and then 1 ml was added. of Toximal TA-15 and the solution was mixed for an additional 30 minutes. A homogeneous mixture was never achieved. However, when a control solution was prepared only the herbicide, water and Toximal TA-15 were used in the same ratios as the sample, a comparable inhomogeneous solution was found.
EXAMPLE 33
At room temperature, 0.6 grams of hydrophilic prepolymer HYPOL® PreMA® G-50 was dissolved in 200 grams of water. 0.5 grams of ethyl chloroimuron, a herbicide, was mixed with the 200 grams of the prepolymer and the aqueous solution. The solution was mixed until it appeared that all the herbicide dissolved. The properties of this solution were consistent with a control solution prepared using only the herbicide and water.
EXAMPLE 34
0.6 grams Hydrophilic Prepolymer HYPOL® PreMA® was dissolved at room temperature
G-50 in 200 grams of water. 0.5 grams of Methyl Tifensulfuron, a herbicide, was mixed, mixed with the 200 grams of the prepolymer and the aqueous solution. The solution was mixed until it appeared that all the herbicide dissolved. The properties of this solution were consistent with a control solution prepared using only the herbicide and water.
EXAMPLE 35
0.6 grams Hydrophilic Prepolymer HYPOL® PreMA® was dissolved at room temperature
G-50 in 200 grams of water. 16 grams of Dicamba, a herbicide, were mixed with the 1500 grams of the prepolymer and the aqueous solution. The solution was mixed until it appeared that all of the herbicide dissolved or dispersed. The solution showed a rapid settlement of some insoluble solids and maintained a milky appearance. However, the solids remained in solution longer than a control of only the herbicide and water.
EXAMPLE 36
At room temperature, 0.5 grams of hydrophilic prepolymer HYPOL® PreMA® G-50 was dissolved in 25 grams of Kelthane, a liquid acaricide. This solution showed no signs of settling or gel formation due to the presence of the prepslimer in the mixture. 10 grams of this mixture were added to 190 grams of water. No problem was seen with mixing. Neither the solution showed signs of settlement after mixing. The properties of this solution were consistent with a control solution prepared using only acaricide and water.
EXAMPLE 37
0.3 grams of hydrophilic prepolymer HYPOL® PreMA® G-50 was dissolved at room temperature in 100 grams of water. 15 grams of Acetate, an insecticide, were mixed with the 85 grams of the prepolymer solution / until it seemed that all the insecticide had dissolved or dispersed. The solution was clear and showed no signs of settlement over time. The properties of this solution were consistent with a control solution prepared using only the insecticide and water.
EXAMPLE 38
At room temperature, 6 grams of hydrophilic prepolymer HYPOL® PreMA® G-50 were dissolved in 94 grams of water. The solution was mixed for 15 minutes. 45 grams of Cloromequat, a plant growth regulator, were added to the solution and mixed for an additional 15 minutes. There were no signs of settling or gel formation of the mixture after mixing or over time indicating compatibility of the compounds.
EXAMPLE 39
Weigh into a container and dissolved at room temperature, sixty grams of hydrophilic prepolymer HYPOL® PreMA® G-50 in 240 grams of deionized water. The solution was then placed in a jacketed beaker in which the constant temperature was maintained at 25 ° C. A magnetic stirrer was used to mix the solution in a controlled temperature environment. At regular intervals, small aliquots (1 ml) of the solution were collected. These aliquots were immediately mixed with 5 ml of a 0.01 N Di-n-butylamine solution. The samples were mixed for at least 30 minutes using a magnetic stirrer. These samples were then placed in a 55 'C oven overnight until all the liquid in the sample evaporated. Next, the samples were weighed and the weights recorded. A residue from clear to white was visible on the bottom of all sample bottles. Next, 10 ml of water was added to each bottle and allowed to settle for at least 1 hour. The liquid portion of the sample was then removed from the flasks and placed on a previously weighed aluminum weighing pan. Then the weighing dish and the flask were placed inside the oven at 55 ° C and kept inside the oven overnight and the water was allowed to evaporate. Each sample was weighed again and the new weight recorded. Changes in weight from the original values were calculated. The data showed that the percentage of the original solution that was dried in the flasks and dissolved in the 10 ml of water decreased while the reaction was allowed to be in progress. The samples collected at the end of the reaction formed clear and stable gels that were hydrophilic and partially soluble in water.
EXAMPLE 40
Thirty grams of hydrophilic prepolymer HYPOL® PreMA® G-50 were weighed into a container and dissolved in 270 grams of deionized water. The solution was then placed in a jacketed beaker in which the constant temperature was maintained at 25 ° C. A magnetic stirrer was used to mix the solution in a controlled temperature environment. At regular intervals, small aliquots (1 ml) of the solution were collected. These aliquots were immediately mixed with 5 ml of a 0.01 N Di-n-butylamine solution. The samples were mixed for at least 30 minutes using a magnetic stirrer. These samples were then placed in an oven at 55 ° C overnight until all the liquid in the sample was evaporated. Next, the samples were weighed and the weights recorded. A residue from clear to white was visible on the bottom of all sample bottles. Next, 10 ml of water was added to each bottle and allowed to settle for at least 1 hour. After the liquid portion of the sample was removed from the jars and placed on an aluminum weighing pan, it was previously weighed. After the weighing plate was placed and the bottle inside the oven at 55 ° C and kept inside the oven overnight and the water was allowed to evaporate. Each sample was weighed again and the new weight recorded. Changes in weight from the original values were calculated. The data showed that the percentage of the original solution that was dried in the flasks and dissolved in the 10 ml of water decreased while the reaction was allowed to be in progress. The samples collected at the end of the reaction formed clear and stable gels that were hydrophilic and partially soluble in water.
EXAMPLE 41
They were weighed into a container and dissolved at room temperature, thirty-seven grams of hydrophilic prepolymer
HYPOL® PreMA® G-50 in 273 grams of deionized water. The solution was then placed in a jacketed beaker in which the constant temperature was maintained at 25 ° C. A magnetic stirrer was used to mix the solution in a controlled temperature environment. At regular intervals, small aliquots (1 ml) of the solution were collected. These aliquots were immediately mixed with 5 ml of a 0.01 N Di-n-butylamine solution. The samples were mixed for at least 30 minutes using a magnetic stirrer. These samples were then placed in an oven at 55 ° C overnight until all the liquid in the sample was evaporated. Next, the samples were weighed and the weights recorded. A residue from clear to white was visible on the bottom of all sample bottles. Next, 10 ml of water was added to each bottle and allowed to settle for at least 1 hour. After the liquid portion of the sample was removed from the jars and placed on an aluminum weighing pan, it was previously weighed. Then the weighing plate and the flask were placed inside the oven at 55 ° C and kept inside the oven overnight and the water was allowed to evaporate. Each sample was weighed again and the new weight recorded. Changes in weight from the original values were calculated. The data showed that the percentage of the original solution that was dried in the flasks and dissolved "in the 10 ml of water decreased while the reaction was allowed to proceed." The samples collected at the end of the reaction formed clear gels and stable that were hydrophilic and partially soluble in water.
EXAMPLE 42
Thirty-four grams of HYPOL® PreMA® G-50 hydrophilic prepolymer were weighed into a container and dissolved at 276 grams of deionized water. The solution was then placed in a jacketed beaker in which the constant temperature was maintained at 25 JC. A magnetic stirrer was used to mix the solution in a controlled temperature environment. At regular intervals, small aliquots (1 ml) of the solution were collected. These aliquots were immediately mixed with 5 ml of a 0.01 N Di-n-butylamine solution. The samples were mixed for at least 30 minutes using a magnetic stirrer. These samples were then placed in an oven at 55 ° C overnight until all the liquid in the sample was evaporated. Next, the samples were weighed and the weights recorded. A residue from clear to white was visible on the bottom of all sample bottles. Next, 10 ml of water was added to each bottle and allowed to settle for at least 1 hour. After the liquid portion of the sample was removed from the jars and placed on an aluminum weighing pan, it was previously weighed. Then the weighing plate and the flask were placed inside the oven at 55 ° C and kept inside the oven overnight and the water was allowed to evaporate. Each sample was weighed again and the new weight recorded. Changes in weight from the original values were calculated. The data showed that the percentage of the original solution that was dried in the flasks and dissolved in the 10 ml of water decreased while the reaction was allowed to be in progress. The samples collected at the end of the reaction formed clear and stable gels that were hydrophilic and partially soluble in water.
EXAMPLE 43
Thirty-four grams of HYPOL® PreMA® G-50 hydrophilic prepolymer were weighed into a container and dissolved at 276 grams of deionized water. The solution was then placed in a jacketed beaker in which the constant temperature was maintained at 25 ° C. A magnetic stirrer was used to mix the solution in a controlled temperature environment. At regular intervals, small aliquots (1 ml) of the solution were collected. These aliquots were immediately mixed with 5 ml of a 0.01 N Di-n-butylamine solution. The samples were mixed for at least 30 minutes using a magnetic stirrer. These samples were then placed in an oven at 55 ° C overnight until all the liquid in the sample was evaporated. Next, the samples were weighed and the weights recorded. A residue from clear to white was visible on the bottom of all sample bottles. Next, 10 ml of water was added to each bottle and allowed to settle for at least 1 hour. After the liquid portion of the sample was removed from the jars and placed on an aluminum weighing pan, it was previously weighed. Then the weighing plate and the flask were placed inside the oven at 55 ° C and kept inside the oven overnight and the water was allowed to evaporate. Each sample was weighed again and the new weight recorded. Changes in weight from the original values were calculated. The data showed that the percentage of the original solution that was dried in the flasks and dissolved in the 10 ml of water decreased while the reaction was allowed to be in progress. The samples collected at the end of the reaction formed clear and stable gels that were hydrophilic and partially soluble in water.
EXAMPLE 44
Eight grams of hydrophilic prepolymer HYPOL® PreMA® G-50 was dissolved in 92 grams of water at 100 ° C, and the solution was mixed for seven hours. Then 14.19 grams of FUNGINEX, a fungicide containing 6.5% Triforine, was added to 50 grams of the prepolymer / water solution. An aliquot of this solution was placed in an aluminum weighing pan and allowed to dry in an oven at 60 ° C overnight. A strong elastic film was obtained.
3.2 grams of water / Triforin solution were diluted in two hundred grams of water. The resulting concentration of Triforine is equivalent to the concentration recommended for commercial use of the product. A stable solution was obtained and a tile was placed inside the aluminum weighing pan and allowed to dry in an oven at 60 ° C overnight. An elastic film was obtained.
EXAMPLE 45
Eight grams of HYPOL® PreMA® G-50 hydrophilic prepolymer were dissolved in 92 grams of water at 25"C, and the solution was mixed for seven hours, then 56.76 grams of SEVIN, an insecticide containing 21.3% Carbaryl, were added. to 150 grams of the prepolymer / water solution.An aliquot of this solution was placed in an aluminum weighing pan and allowed to dry in a 60"C oven overnight. A strong elastic film was obtained.
2.06 grams of water / carbaryl solution were diluted in 120 grams of water. The resulting concentration of Carbaryl is equivalent to the concentration recommended for commercial use of the product. A stable solution was obtained and a tile was placed inside the aluminum weighing pan and allowed to dry in an oven at 60 ° C overnight. An elastic film was obtained.
EXAMPLE 46
Eight grams of hydrophilic prepolymer HYPOL® PreMA® G-50 was dissolved in 92 grams of water at 25 ° C, and the solution was mixed for seven hours. Then 28.38 grams of DACONIL, a fungicide containing 29.6% Clorothalonil, was added to 75 grams of the prepolymer / water solution. The solution was mixed and appeared homogeneous and continued even after twenty-four hours. An aliquot of this solution was placed in an aluminum weighing pan and allowed to dry in an oven at 60 ° C overnight. A strong elastic film was obtained.
2.06 grams of water solution / Chlorothalonil were diluted in 120 grams of water. The resulting concentration of Chlorothalonil is equivalent to the concentration recommended for commercial use of the product. A stable solution was obtained and a tile was placed inside the aluminum weighing pan and allowed to dry in an oven at 60 ° C overnight. An elastic film was obtained.
It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present invention.
Having described the invention as above, the content of the following is claimed as property.
Claims (17)
1. A pesticide composition, characterized in that it comprises an aqueous solution of an pesticidally effective amount of pesticide; and a subgealing amount of a hydratable hydrophilic polyurethane or polyurea urethane polymer that forms a gel.
2. The pesticidal composition of claim 1, characterized in that said hydrophilic polymer is formed of a prepolymer selected from the group consisting of toluene diisocyanate polyethylene glycol trimethylolpropane, homopolymer of methylene diisocyanate-methylene diisocyanate-methylene diisocyanate methylene diisocyanate polyethylene glycol polymer, toluene diisocyanate and polymer of ethylene oxide and propylene oxide with trimethylolpropane, isophorone diisocyanate and polymer of ethylene oxide - propylene oxide - trimethylolpropane, toluene diisocyanate polyethylene glycol trilactate, and polyethylene glycol terminated with toluene diisocyanate.
3. The pesticidal composition of claim 1, characterized in that it also comprises an effective amount of an activating surfactant.
4. The pesticidal composition of claim 3, characterized in that it further comprises said surfactant selected from the group consisting of alkylbenzene and alkylnaphthalene sulfonates, polyoxyethylene alkylphenol, sulfated fatty alcohols, acid amines or amides, sodium isethionate esters of long chain acids, esters of sodium sulfosuccinate, petroleum sulfonates of sulfonated fatty acid esters, N-acyl amino acids such as sarcocinates, alkyl polyglucosides, ethoxylated alkylamines, alkyl ethoxylated alcohols, and quaternary alkyl or alkylarylamines mixtures.
5. The pesticidal composition of claim 1, characterized in that it further comprises an additive selected from the group consisting of the group consisting of polyethylene glycol, diethylene glycol, ethylene glycol, methanol, ethanol, 2-propanol, butanol, hexanol and heptanol.
6. A method for controlling pests, characterized in that it comprises administering to said pests or to the site thereof an effective amount of a composition comprising an aqueous solution of a pesticidally effective amount of a pesticide; an amount of subgelation of a hydrophilic polyurethane or polyurea urethane polymer that forms a hydratable gel.
7. The method of claim 6, characterized in that said composition further comprises an effective amount of an activating surfactant.
8. The method of claim 7, characterized in that said surfactant selected from the group consisting of alkylbenzene and alkylnaphthalene sulfonates, alkylphenol polyoxyethylene, sulfated fatty alcohols, amines or acid amides, sodium isethionate esters of long chain acids, sulfosuccinate esters of sodium, sulfonates of petroleum of esters of sulfonated fatty acids, N-acyl amino acids such as sarcocinates, alkyl polyglucosides, alkylethoxylated amines, alkyl ethoxylated alcohols, and mixtures of alkyl or alkylarylamines quaternary.
9. A delivery system for supplying a pesticidal composition to a substrate, characterized in that said delivery system comprises an aqueous solution of a subgelation amount of a hydrophilic polymer forming a hydratable gel selected from a group consisting of polyurethane urethane and polyurethane, and a pesticidally effective amount of pesticide; and means for supplying said solution to said substrate.
10. The delivery system of claim 9, characterized in that said pesticide is a member selected from the group consisting of an insecticide, a herbicide, a nematocide, a fungicide, a plant regulator, a defoliant, and a desiccant.
11. The delivery system of claim 9, characterized in that it further comprises an effective amount of an activating surfactant.
12. The delivery system of claim 11, characterized in that said surfactant is selected from the group consisting of alkylbenzene and alkylnaphthalene sulfonates., alkylphenol polyoxyethylene, sulfated fatty alcohols, amines or acidic amides, sodium isethionate esters of long chain acids, sodium sulfosuccinate esters, petroleum sulfonates of sulfonated fatty acid esters, N-acyl amino acids such as sarcocinates, alkyl polyglucosides , alkylethoxylated amines, alkyl ethoxylated alcohols, and mixtures of quaternary alkyl or alkylarylamines.
13. A method for formulating a pesticidal composition, characterized in that it comprises forming a hydrophilic polymer reaction product formed of a prepolymer selected from the group consisting of polyurea urethane, polyurea and polyurethane and an activating surfactant; adding to said reaction product a pesticidally effective amount of a pesticide.
14. A pesticide composition, characterized in that it comprises an elastic film formed with the evaporation of water from an aqueous solution of an pesticidally effective amount of pesticide; and a subgealing amount of a hydratable hydrophilic polyurethane or polyurea urethane polymer that forms a gel.
15. The pesticidal composition of claim 14, characterized in that said aqueous solution further comprises an activating surfactant.
16. The pesticidal composition of claim 14, characterized in that said hydrophilic polymer is formed of a prepolymer selected from the group consisting of toluene diisocyanate polyethylene glycol trimethylolpropane, homopolymer of methylene diisocyanate-methylene diisocyanate-methylene diisocyanate methylene diisocyanate polyethylene glycol polymer, toluene diisocyanate and polymer of ethylene oxide and propylene oxide with trimethylolpropane, isophorone diisocyanate and polymer of ethylene oxide - propylene oxide - trimethylolpropane, toluene diisocyanate polyethylene glycol trilactate, and polyethylene glycol terminated with toluene diisocyanate.
17. The. The pesticidal composition of claim 15, characterized in that said surfactant is selected from the group consisting of alkylbenzene and alkylnaphthalene sulfonates, polyoxyethylene alkylphenol, sulphated fatty alcohols, amines or acid amides, sodium isethionate esters of long chain acids, sulfosuccinate esters of sodium, sulfonates of petroleum of esters of sulfonated fatty acids, N-acyl amino acids such as sarcocinates, alkyl polyglucosides, alkylethoxylated amines, alkylethoxylated alcohols, and mixtures of alkyl or alkylarylamines quaternary.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08693375 | 1996-08-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA99001168A true MXPA99001168A (en) | 1999-09-01 |
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