NZ599091B - Granule composition containing herbicide and method for preparation thereof - Google Patents
Granule composition containing herbicide and method for preparation thereof Download PDFInfo
- Publication number
- NZ599091B NZ599091B NZ599091A NZ59909112A NZ599091B NZ 599091 B NZ599091 B NZ 599091B NZ 599091 A NZ599091 A NZ 599091A NZ 59909112 A NZ59909112 A NZ 59909112A NZ 599091 B NZ599091 B NZ 599091B
- Authority
- NZ
- New Zealand
- Prior art keywords
- water
- oxyfluorfen
- weight
- granule
- miscible
- Prior art date
Links
- 230000002363 herbicidal Effects 0.000 title claims abstract description 70
- 239000004009 herbicide Substances 0.000 title claims abstract description 35
- 239000008202 granule composition Substances 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 239000008187 granular material Substances 0.000 claims abstract description 176
- 239000005590 Oxyfluorfen Substances 0.000 claims abstract description 162
- OQMBBFQZGJFLBU-UHFFFAOYSA-N Oxyfluorfen Chemical compound C1=C([N+]([O-])=O)C(OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 OQMBBFQZGJFLBU-UHFFFAOYSA-N 0.000 claims abstract description 162
- 239000005587 Oryzalin Substances 0.000 claims abstract description 90
- UNAHYJYOSSSJHH-UHFFFAOYSA-N Oryzalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O UNAHYJYOSSSJHH-UHFFFAOYSA-N 0.000 claims abstract description 90
- 239000007788 liquid Substances 0.000 claims abstract description 83
- 239000000969 carrier Substances 0.000 claims abstract description 78
- 239000007787 solid Substances 0.000 claims abstract description 24
- 239000000203 mixture Substances 0.000 claims description 62
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 53
- 150000002894 organic compounds Chemical class 0.000 claims description 25
- -1 glycol ethers Chemical class 0.000 claims description 18
- 229960000892 attapulgite Drugs 0.000 claims description 17
- 229910052625 palygorskite Inorganic materials 0.000 claims description 17
- 229920001223 polyethylene glycol Polymers 0.000 claims description 16
- 239000004927 clay Substances 0.000 claims description 15
- 229910052570 clay Inorganic materials 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 229920002521 Macromolecule Polymers 0.000 claims description 11
- HWKQNAWCHQMZHK-UHFFFAOYSA-N Trolnitrate Chemical compound [O-][N+](=O)OCCN(CCO[N+]([O-])=O)CCO[N+]([O-])=O HWKQNAWCHQMZHK-UHFFFAOYSA-N 0.000 claims description 11
- 239000000440 bentonite Substances 0.000 claims description 11
- 229910000278 bentonite Inorganic materials 0.000 claims description 11
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Substances OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 11
- 238000011068 load Methods 0.000 claims description 11
- 238000001816 cooling Methods 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 150000002170 ethers Chemical class 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 6
- 239000002250 absorbent Substances 0.000 claims description 5
- 230000002745 absorbent Effects 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 229920002678 cellulose Polymers 0.000 claims description 4
- 239000001913 cellulose Substances 0.000 claims description 4
- 150000002334 glycols Chemical class 0.000 claims description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims 2
- 239000004698 Polyethylene (PE) Substances 0.000 claims 1
- 229920001515 polyalkylene glycol Polymers 0.000 claims 1
- 229920000573 polyethylene Polymers 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 62
- 239000000463 material Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 12
- 240000000161 Lagerstroemia indica Species 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 10
- 240000001949 Taraxacum officinale Species 0.000 description 10
- 231100000674 Phytotoxicity Toxicity 0.000 description 8
- 239000002202 Polyethylene glycol Substances 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 235000014079 dandelion Nutrition 0.000 description 8
- 235000009242 dandelion Nutrition 0.000 description 8
- 238000003860 storage Methods 0.000 description 8
- 241000057751 Allocasuarina littoralis Species 0.000 description 7
- PZZYQPZGQPZBDN-UHFFFAOYSA-N Aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 7
- 240000006694 Stellaria media Species 0.000 description 7
- 239000005995 Aluminium silicate Substances 0.000 description 6
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 6
- 240000008059 Nerium oleander Species 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 235000012211 aluminium silicate Nutrition 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 6
- 239000000428 dust Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000000007 visual effect Effects 0.000 description 6
- 239000001856 Ethyl cellulose Substances 0.000 description 5
- 240000007505 Fumaria officinalis Species 0.000 description 5
- 241000595422 Hypochaeris radicata Species 0.000 description 5
- 229920001249 ethyl cellulose Polymers 0.000 description 5
- 235000019325 ethyl cellulose Nutrition 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 241000404068 Cotula Species 0.000 description 4
- 235000006961 Fumaria officinalis Nutrition 0.000 description 4
- VAYOSLLFUXYJDT-RDTXWAMCSA-N LSD Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N(CC)CC)C2)=C3C2=CNC3=C1 VAYOSLLFUXYJDT-RDTXWAMCSA-N 0.000 description 4
- 229950002454 Lysergide Drugs 0.000 description 4
- 238000005054 agglomeration Methods 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinylpyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 3
- LZGUHMNOBNWABZ-UHFFFAOYSA-N N-nitro-N-phenylnitramide Chemical compound [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 description 3
- 229920003081 Povidone K 30 Polymers 0.000 description 3
- 235000002594 Solanum nigrum Nutrition 0.000 description 3
- 240000006258 Solanum nigrum Species 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 235000010419 agar Nutrition 0.000 description 3
- WMGSQTMJHBYJMQ-UHFFFAOYSA-N aluminum;magnesium;silicate Chemical compound [Mg+2].[Al+3].[O-][Si]([O-])([O-])[O-] WMGSQTMJHBYJMQ-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 235000010980 cellulose Nutrition 0.000 description 3
- 239000000084 colloidal system Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 3
- 239000008108 microcrystalline cellulose Substances 0.000 description 3
- 229940016286 microcrystalline cellulose Drugs 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N oxo-oxoalumanyloxy-[oxo(oxoalumanyloxy)silyl]oxysilane;dihydrate Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 235000005510 plains black nightshade Nutrition 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-Dichlorophenoxyacetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 2
- VUKAUDKDFVSVFT-UHFFFAOYSA-N 2-[6-[4,5-bis(2-hydroxypropoxy)-2-(2-hydroxypropoxymethyl)-6-methoxyoxan-3-yl]oxy-4,5-dimethoxy-2-(methoxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)-5-methoxyoxane-3,4-diol Chemical compound COC1C(OC)C(OC2C(C(O)C(OC)C(CO)O2)O)C(COC)OC1OC1C(COCC(C)O)OC(OC)C(OCC(C)O)C1OCC(C)O VUKAUDKDFVSVFT-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 description 2
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 description 2
- 229920002594 Polyethylene Glycol 8000 Polymers 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N Triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 238000004166 bioassay Methods 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 235000005824 corn Nutrition 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- KARVSHNNUWMXFO-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane;hydrate Chemical compound O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Al]O[Al]=O KARVSHNNUWMXFO-UHFFFAOYSA-N 0.000 description 2
- WRZXKWFJEFFURH-UHFFFAOYSA-N dodecaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO WRZXKWFJEFFURH-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052901 montmorillonite Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 229920001888 polyacrylic acid Polymers 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011164 primary particle Substances 0.000 description 2
- 239000011163 secondary particle Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- 238000004450 types of analysis Methods 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N Ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229960003563 Calcium Carbonate Drugs 0.000 description 1
- 240000000218 Cannabis sativa Species 0.000 description 1
- 241000219501 Casuarina Species 0.000 description 1
- 241001465373 Epilobium ciliatum Species 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- 229940095686 Granule Product Drugs 0.000 description 1
- 235000010678 Paulownia tomentosa Nutrition 0.000 description 1
- 239000005591 Pendimethalin Substances 0.000 description 1
- CHIFOSRWCNZCFN-UHFFFAOYSA-N Pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 1
- 229920002556 Polyethylene Glycol 300 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241000124033 Salix Species 0.000 description 1
- 241000207763 Solanum Species 0.000 description 1
- 241000193241 Solanum dulcamara Species 0.000 description 1
- 235000000336 Solanum dulcamara Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N Trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 244000153888 Tung Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- DGMCGTFMFPEQLT-UHFFFAOYSA-M aluminum;magnesium;silicon;hydroxide;tetradecahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.O.O.[OH-].[Mg].[Mg].[Al].[Al].[Si].[Si].[Si].[Si] DGMCGTFMFPEQLT-UHFFFAOYSA-M 0.000 description 1
- 235000019395 ammonium persulphate Nutrition 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 238000004164 analytical calibration Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 230000002498 deadly Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 244000037666 field crops Species 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000010150 least significant difference test Methods 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 238000001543 one-way ANOVA Methods 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 239000011044 quartzite Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000717 retained Effects 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001187 sodium carbonate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Abstract
Patent 599091 GRANULE COMPOSITION CONTAINING HERBICIDE AND METHOD FOR PREPARATION THEREOF Disclosed is a herbicidal broadcast granule comprising at least one of oxyfluorfen and oryzalin in solid form in an amount of no more than 8 per cent by weight oxyfluorfen and no more than 8 per cent by weight oryzalin based on the total granule and a water-miscible carrier liquid in which the at least one of oxyfluorfen and oryzalin is soluble in an amount of at least 8 per cent w/w at a temperature of 60 degrees C. eight oryzalin based on the total granule and a water-miscible carrier liquid in which the at least one of oxyfluorfen and oryzalin is soluble in an amount of at least 8 per cent w/w at a temperature of 60 degrees C.
Description
Patent Form No. 5
NEW ZEALAND
Patents Act 1953
COMPLETE SPECIFICATION
TITLE: GRANULE COMPOSITION CONTAINING HERBICIDE AND METHOD FOR
PREPARATION THEREOF
We Eureka! AgResearch Pty Ltd, of Unit 2, 25-27 Burns Road, Altona, Victoria, 3018, Australia, do
hereby declare the invention, for which we pray that a patent may be granted to us, and the
method by which it is to be performed, to be particularly described in and by the following
statement:
4003q
Granule Composition Containing Herbicide and Method for
Preparation Thereof
This application claims priority from Australian provisional application number
2011901213 filed on 1 April 2011, the contents of which are incorporated herein by
this reference.
Field
This invention relates to granular compositions that comprise at least one of the
herbicides oxyfluorfen and oryzalin and method for preparing the compositions. In
particular, the invention relates to granular compositions that comprise at least one of
oxyfluorfen and oryzalin in an amount of no more than 8% w/w oxyfluorfen and no
more than 8% w/w oryzalin.
Background
Oxyfluorfen and oryzalin are herbicides used for broad spectrum pre- and
post-emergent control of annual broadleaf and grassy weeds in a variety of tree
fruit, nut, vine, and field crops. They are also used in weed control in forestry uses.
Oxyfluorfen and oryzalin are difficult to formulate as a broadcast granule due to poor
solubility in many solvents. As a consequence of this poor solubility in many solvents
clay granules with these herbicides have been prepared using non-polar solvents
such as “Solvesso 150” which is a mixture of alkyl substituted aromatics which
provide good solubility.
Oxyfluorfen granules made utilising many solvents for oxyfluorfen tend form a fine
dust rich in oxyfluorfen during storage. We believe the formation of the dust is due to
the tendency of many of these solvents to gradually evaporate. This promotes the
formation of crystallites of oxyfluorfen at the surface of the granules. We believe that
solvent and oxyfluorfen in the granules are drawn to the granule surface to replace
material lost by evaporation by evaporation resulting in much of the oxyfluorfen
“blooming” onto the surface of the granule over time. The crystallites formed by
evaporation tend to dislodge from the granules in storage and handling, and fall to the
bottom of the container. The result is a dust of the active agent oxyfluorfen and a
non-uniform granule product that comprises “hot regions” with undesirably high
concentrations of herbicide and reduced loading on the interior of the granules. Also,
granules comprising oxyfluorfen are frequently used in confined spaces such as
sheds and greenhouses, and the presence of a strong solvent odour in the granules
is an impediment to a safe and pleasant work environment.
The discussion of documents, acts, materials, devices, articles and the like is included
in this specification solely for the purpose of providing a context for the present
invention. It is not suggested or represented that any or all of these matters formed
part of the prior art base or were common general knowledge in the field relevant to
the present invention as it existed before the priority date of each claim of this
application.
It would be desirable to provide a broadcast granule comprising at least one of
oxyfluorfen and oryzalin that is of more stable and consistent composition, and that
can readily be used in a confined work environment.
Summary
We provide a herbicidal broadcast granule comprising at least one of oxyfluorfen and
oryzalin in amounts of no more than 8% by weight oxyfluorfen and no more than 8%
by weight oryzalin, based on the total granule and a water-miscible carrier liquid in
which at least one of oxyfluorfen and oryzalin is soluble in an amount of at least 8%
w/w at a temperature of 60 C (more preferably at least 15%, more preferably at least
20% and still more preferably at least 25% w/w at 60 C).
In a preferred embodiment, we provide a herbicidal broadcast granule comprising at
least one of oxyfluorfen and oryzalin in solid form in an amount of no more than 8%
by weight oxyfluorfen and no more than 8% by weight oryzalin based on the total
granule and a water-miscible carrier liquid in which the at least one of oxyfluorfen and
oryzalin is soluble in an amount of at least 8% w/w at a temperature of 60 C.
In a preferred embodiment, we provide an oxyfluorfen broadcast granule comprising
no more than 8% by weight oxyfluorfen based on the total granule weight and a
water-miscible carrier liquid in which oxyfluorfen is soluble in an amount of at least 8%
on a weight/weight basis at a temperature of 60ºC, more preferably at least 15%, still
more preferably at least 20% and even more preferably at least 25% w/w at 60 C.
In a preferred embodiment, we provide a herbicidal broadcast granule comprising
oxyfluorfen in solid form in an amount of up to 8% by weight/weight oxyfluorfen based
on the total granule weight and a water-miscible carrier liquid in which oxyfluorfen is
soluble in an amount of at least 8% weight/weight at a temperature of 60ºC.
The carrier liquid preferably comprises a water miscible organic compound which is
preferably a liquid at 120 C preferably a liquid at 80 C. In one embodiment the
organic compound is a liquid at 60 C.
We further provide a method of forming a herbicidal broadcast granule comprising at
least one of oxyfluorfen and oryzalin in an amount of no more than 8% by weight
oxyfluorfen and no more than 8% oryzalin based on the total granule weight, the
method comprising:
providing a solution of at least one of oxyfluorfen and oryzalin in a
mixture at an elevated temperature of preferably at least 40 C (more preferably
at least 50 C, still more preferably at least 55 C and most preferably, about
60 C), the mixture comprising:
(i) water miscible carrier liquid in which at least one of oxyfluorfen and
oryzalin is soluble in an amount of at least 8% by weight at a
temperature of 60 C based on the weight of water miscible carrier liquid
and preferably in which at least one of oxyfluorfen and oryzalin is
soluble in an amount of at least 15% by weight at a temperature 60 C
based on the weight of water miscible solvent, and preferably in which
at least one of oxyfluorfen an oryzalin is soluble in an amount of at least
% by weight oxyfluorfen at a temperature 60 C based on the weight
of water miscible carrier liquid;
(ii) water comprising at least 10% of the water-miscible carrier liquid on a
weight/weight basis;
applying the mixture at an elevated temperature (preferably of at
least 40 C, more preferably at least 50 C, still more preferably at least
55 C and most preferably, about 60 C) to absorbent clay granules to
provide active herbicide loaded granules having a loading of at least oe
of oxyfluorfen and oryzalin of up to 8% by weight of the total weight of
loaded granules; and
preferably further comprising cooling the granules to precipitate
at least one of oxyfluorfen and oryzalin within the granules.
The mixture, in a preferred embodiment, is a solution comprising at least one of
exyfluorfen and oryzalin (preferably at least oxyfluorfen and most preferably both
oxyfluorfen and oryzalin) dissolved therein.
We further provide a method of forming a herbicidal broadcast granule comprising at
least one of oxyfluorfen and oryzalin in crystalline solid form in an amount of no
more than 8% by weight oxyfluorfen and no more than 8% oryzalin based on
the total granule weight, the method comprising:
providing a solution of at least one of oxyfluorfen and oryzalin in a water-
miscible carrier liquid at an elevated temperature of at least 40 C, in which
said at least one of oxyfluorfen and oryzalin is soluble in an amount of at least
8% by weight at a temperature of 60 C based on the weight of water-miscible
carrier liquid;
wherein the water-miscible carrier liquid comprises a water-miscible
organic compound and water in an amount of at least 10% on a weight by
weight basis of the water-miscible carrier liquid;
and
applying the solution at an elevated temperature to absorbent clay
granules to provide active herbicide loaded granules having a loading of at
least one of oxyfluorfen and oryzalin of up to 8% by weight of the total weight of
loaded granules; and
cooling the granules to precipitate at least one of oxyfluorfen and
oryzalin within the granules.
We further provide a method of forming an oxyfluorfen broadcast granule comprising
up to 8% by weight oxyfluorfen based on the total granule weight, the method
comprising:
providing a solution of oxyfluorfen in a mixture at an elevated
temperature of preferably at least 40 C (more preferably at least 50 C, still
more preferably at least 55 C and most preferably, about 60 C), the mixture
comprising:
(i) water miscible carrier liquid in which oxyfluorfen is soluble in an
amount of at least 8% by weight oxyfluorfen at a temperature of
60ºC based on the weight of water miscible carrier liquid, and
preferably in which oxyfluorfen is soluble in an amount of at least
% by weight oxyfluorfen at a temperature 60ºC based on the
weight of water miscible solvent, and preferably in which oxyfluorfen
is soluble in an amount of at least 20% by weight oxyfluorfen at a
temperature 60ºC based on the weight of water-miscible carrier
liquid;
(ii) water comprising at least 10% of the water-miscible carrier liquid on
a weight/weight basis;
applying the mixture at an elevated temperature (preferably of at least
o o o
40 C, more preferably at least 50 C, still more preferably at least 55 C and
most preferably, about 60 C) to absorbent clay granules to provide active
loaded granules having a loading of oxyfluorfen of up to 8% oxyfluorfen by
weight of the total weight of loaded granules; and
preferably further comprising cooling the granules to precipitate
oxyfluorfen within the granules.
We further provide a method of forming an oxyfluorfen broadcast granule comprising
oxyfluorfen in crystalline solid form in an amount up to 8% by weight
oxyfluorfen based on the total granule weight, the method comprising:
providing a solution of oxyfluorfen in a water-miscible carrier liquid at an
elevated temperature of at least 50 C, in which oxyfluorfen is soluble in an
amount of at least 25% by weight oxyfluorfen at a temperature of 60ºC based
on the weight of water-miscible carrier liquid; and
wherein the water-miscible carrier liquid comprises a water-miscible
organic compound and water in an amount of at least 10% on a weight by
weight basis of the water-miscible carrier liquid; and
wherein the solubility of oxyfluorfen in the water-miscible carrier liquid is
no more than 5% w/w at 20ºC by weight oxyfluorfen based on the weight of
the mixture; and
applying the solution at an elevated temperature of at least 50 C to clay
granules to provide active loaded granules having a loading of oxyfluorfen of
up to 8% oxyfluorfen by weight of the total active loaded granules absorbed
into the granules; and
cooling the granules to precipitate oxyfluorfen within the granules.
Generally we have found that the use of water soluble solvents and in particular the
mixture of water-miscible organic solvent and water to absorb the oxyfluorfen into the
granule reduces significantly the occurrence of fines in the granule composition
particularly with storage and handling of the granule composition. Further the ability
to use water-miscible organic solvents generally allows compositions to be prepared
without the odour problem caused by the water-immiscible aromatic hydrocarbons
previously used as solvent for manufacture of oxyfluorfen granules.
The preferred granules comprise oxyfluorfen in an amount of from 0.1% w/w to 8%
w/w of the granule composition, more preferably 0.5% w/w to 5% w/w and still more
preferably 0.5% w/w to 3% w/w of the granule composition.
The granules may contain oryzalin as the herbicidal active which may be the sole
active or may be in addition to oxyfluorfen. Oryzalin, in one set of embodiments, is
present in an amount in the range of from 0.1% w/w to 8% w/w of the granule
composition, more preferably 0.5% w/w to 4% w/w and still more preferably 0.5% w/w
to 1.5% w/w of the granule composition.
The granules may comprise other herbicides or active agents if desired. However, in
one embodiment, the granule comprises no more than 2% of herbicidal active other
than one or both of oxyfluorfen and oryzalin and more preferably no more than 1%
w/w other herbicide.
Throughout the description and the claims of this specification the word “comprise”
and variations of the word, such as “comprising” and “comprises” is not intended to
exclude other additives, components, integers or steps.
Detailed Description
In one aspect there is provided a herbicidal broadcast granule comprising at least one
of oxyfluorfen and oryzalin an an amount of no more than 8% by weight oxyfluorfen
based on the granule weight and no more than 8% w/w oryzalin based on the total
granule weight and a water-miscible carrier liquid in which at least one of oxyfluorfen
and oryzalin is soluble in an amount of at least 8% on a weight/weight basis at a
temperature of 60ºC, more preferably at least 15% and more preferably at least 20%
w/w at 60 C.
In a preferred aspect, there is provided an oxyfluorfen broadcast granule comprising
no more than 8% by weight oxyfluorfen based on the total granule weight and a
water-miscible carrier liquid in which oxyfluorfen is soluble in an amount of at least 8%
on a weight/weight basis at a temperature of 60 C, more preferably at least 15% and
more preferably at least 20%.
The water-miscible carrier liquid comprises a water-miscible organic compound and
preferably also comprises water. The ratio of water miscible organic compound to
water is preferably in the range of from 10:1 to 1:1 on a volume/volume basis, and
preferably the volume ratio is in the range 6:1 to 2:1.
The term water-miscible liquid carrier refers to a water-miscible organic compound,
optionally in admixture with water.
The term water miscible organic compound refers to compounds comprising carbon
and hydrogen and preferably at least carbon, hydrogen and oxygen and mixtures of
such compounds. Such compounds may optionally further comprise additional
elements such as sulfur, nitrogen, phosphorus or the like. Compounds which are
liquids at 120ºC (preferably liquid at 80ºC such as 60 C) are preferred and such
compounds consisting of the elements carbon, hydrogen and oxygen are particularly
preferred. The water-miscible organic liquid is preferably miscible in a 1 : 1 volume
ratio (or greater proportion of water-miscible organic liquid) with water at 20 C.
Examples of water-miscible organic carrier may, for example, be selected from the
group consisting of C to C alkyl mono ethers of di- and tri-(C to C alkylene) glycols
1 6 2 4
and poly(alkylene glycol) particularly polyethylene glycol. More preferred water-
miscible organic compounds are C to C alkyl mono ethers of at least one of
diethylene glycol and triethylene glycol and polyethylene glycols of molecular weight
from 200 to 10,000. One preferred class of water-miscible organic compounds are
diethylene glycol mono alkyl ethers and triethylene glycol mono alkyl ethers wherein
the alkyl is selected from methyl, ethyl, propyl and butyl and most preferably,
diethylene glycol monobutyl ether.
The oxyfluorfen is preferably present in the granule composition as a particulate solid,
preferably a crystalline particulate solid of solubility no more than 10% of the water-
miscible carrier liquid on a weight/weight basis at 20 C, preferably no more than 5%
and most preferably no more than 3% at 20 C.
The oryzalin may be present in the granule and when present is preferably a
crystalline particulate solid of solubility no more than 10% w/w in the water-miscible
carrier liquid at 20 C, preferably no more than 5% w/w and more preferably no more
than 3% and still more preferably no more than 1% w/w at 20 C.
The porous carrier granule is preferably a clay granule, preferably attapulgite or
bentonite. The granule is preferably a coarse broadcast granule and is preferably not
dispersible in water. The granule size is preferably in the range 0.2 – 4mm, more
preferably in the size range 0.5 – 1.5 mm.
Generally the granule composition may be free from surfactants although such
materials may be added if desired. Thus in one embodiment the granule composition
comprises less than 5% by weight surfactant (preferably less than 2% by weight and
still more preferably less than 1% by weight and most preferably is free of added
surfactant).
The oxyflurofen is preferably present in the granule in solid form and more preferably
in a form crystallised from a mixture of the water-miscible carrier liquid and water
absorbed into the granule at elevated temperature.
The water-miscible organic compounds are preferably selected from the group
consisting of glycol ethers, preferably mono-(C to C alkyl)ethers of di- or tri-(C to C
1 6 2 4
alkylene)glycols and preferably polyethylene glycols of molecular weight 200 to
,000. One group of such compounds are diethylene glycol mono alkyl ethers and
triethylene glycol mono alkyl ethers wherein the alkyl is selected from methyl, ethyl,
propyl and butyl, and most preferably diethylene glycol mono butyl ether.
The water-miscible carrier liquid is preferably present in the granule composition in an
amount of from 2% more preferably from 5% weight by weight. The upper limit will be
governed by the specific composition but is typically no more than 20%, preferably no
more than 15% and still more preferably no more than 12% weight by weight of the
total granule composition.
In one preference the water-miscible organic compound with a low degree of odour is
blended with water to provide a polar liquid blend. Preferably the volume/volume ratio
of water-miscible organic solvent to water is in the range 10:1 to 1:1.
In one set of embodiments the oxyfluorfen broadcast granule further comprising a
water soluble tackifying agent. The water soluble macromolecule (preferably a
polymer) is preferably a polymer and is preferably selected from the group consisting
of polyvinyl pyrrolidine and cellulosic polymers such as hydroxypropylmethyl cellulose
and ethyl cellulose. Polyethylene glycol may provide the role of water-miscible
organic compound and tackifying agent.
In one embodiment, the composition is a blend of polyethylene glycols of different
molecular weight, for example, one PEG of molecular weight up to 600 and one PEG
of molecular weight above 600 such as 800 or above.
Preferably the ratio of water-soluble macromolecule to water-miscible carrier liquid
(on a weight/weight basis) is in the range 0.03 to 0.15. More preferably the ratio of
the water-soluble macromolecule to polar liquid is about 0.05 – 0.1.
In one set of embodiments there is provided a method of forming an oxyfluorfen
broadcast granule comprising up to 8% by weight oxyfluorfen based on the total
granule weight, the method comprising:
providing a solution of oxyfluorfen in a mixture at an elevated
temperature of preferably at least 40 C ( more preferably at least 50 C, still
more preferably at least 55 C and most preferably, about 60 C), the mixture
comprising:
(i) water-miscible carrier liquid in which oxyfluorfen is soluble in an
amount of at least 8% by weight oxyfluorfen at a temperature of
60ºC based on the weight of water-miscible carrier liquid, and
preferably in which oxyfluorfen is soluble in an amount of at least
15% by weight oxyfluorfen at a temperature 60 C based on the
weight of water-miscible solvent, and preferably is which oxyfluorfen
is soluble in an amount of at least 20% by weight oxyfluorfen at a
temperature 60 C based on the weight of water-miscible solvent;
(ii) water comprising at least 10% of the water-miscible carrier liquid on
a weight/weight basis;
applying the mixture at an elevated temperature (preferably of at least
o o o
40 C, more preferably at least 50 C, still more preferably at least 55 C and
most preferably, about 60 C) to absorbent clay granules to provide active
loaded granules having a loading of oxyfluorfen of up to 8% oxyfluorfen by
weight of the total weight of loaded granules; and
preferably further comprising cooling the granules to precipitate
oxyfluorfen within the granules.
The weight ratio of water miscible organic liquid to water used in the method is
preferably in the range of from 10:1 to 1:1 on a weight/weight basis and wherein the
water miscible organic liquid is used in a ratio with water in which it is miscible at the
temperature at which the mixture is applied.
The water miscible organic liquid is preferably selected from the group consisting of
C to C alkyl mono ethers of di and tri C to C alkylene glycols, preferably C to C
1 6 2 4 1 6
alkyl mono ethers of at least one of diethylene glycol and triethylene glycol, more
preferably diethylene glycol mono alkyl ethers and triethylene glycol mono alkyl ethers
wherein the alkyl is selected from methyl, ethyl, propyl and butyl and most preferably,
diethylene glycol monobutyl ether.
The method will generally result in the oxyflurofen being at least partially crystallised
from the water miscible carrier liquid absorbed into the granule at elevated
temperature.
The cooling to provide crystallisation may take place under ambient conditions
following application of the mixture to the granules.
The mixture applied to the granular composition may in preferred embodiments
comprise in the range of from 10 to 80% by weight oxyfluorfen.
In one embodiment the granules of the invention further comprise an additional
herbicide particularly a dinitroaniline herbicide particularly oryzalin. Preferably the
dinitroaniline herbicide is chosen from the group consisting of oryzalin, pendimethalin
and trifluralin. Preferably the dinitroaniline herbicide is oryzalin. Preferably oryzalin
comprises 0.3 – 3% weight by weight of the final composition. In one set of
embodiments the composition of the invention comprises 1 – 3% weight oxyfluorfen
and further comprises 0.5 - 1.5% by weight oryzalin based on the weight of the total
composition. More preferably the granule composition comprises 1 – 3% oxyfluorfen
and further comprises 0.5 – 1.5% oryzalin on a weight/weight basis, and still more
preferably the broadcast granule comprises 1.5 – 2.5% oxyfluorfen and further
comprises 0.7 – 1.3% oryzalin.
More preferably the composition of the invention comprises about 2% by weight
oxyfluorfen and about 1% by weight oryzalin. The oxyfluorfen and oryzalin materials
are preferably dissolved together in the carrier liquid at elevated temperature of at
o o o
least 40 C, more preferably at least 50 C, still more preferably at least 55 C and most
preferably, about 60 C prior to application of said liquid to the carrier granule.
The loading of oxyfluorfen on the granules is in one set of embodiments in the range
of from 0.1% to 8% by weight, more preferably from 0.5% to 5% and most preferably
from 0.5 to 3% by weight.
When the granule composition comprises both oxyfluorfen and oryzalin it is preferred
that the method involves dissolving both oxyfluorfen and oryzalin in the mixture at
elevated temperature preferably at least 40 C, more preferably at least 50 C and still
more preferably at least 60 C and cooling the granule composition (preferably to
ambient temperature) after applying the mixture to the granules.
The granule composition comprises a solid carrier. Examples of solid carriers useful
for formulating the granular herbicides include clay, bentonite, talc, calcium
carbonate, sodium carbonate, zeeklite, sericite, acid clay, quartzite, diatomaceous
silica, pumice, zeolite, vermiculite, potassium chloride, urea, white carbon, ammonium
sulfate, sodium sulfate, perlite, magnesium sulfate, kaolin, attapulgite and the like;
The more preferred carriers are generally attapulgite and kaolin including sodium
kaoline and potassium kaolin and mixtures thereof.
In one embodiment, the granule composition is prepared by agglomeration of powder.
It is preferred, however, that the solid carrier used in preparing the granule
composition is not an agglomerate, that is, the granule composition is of primary
particles onto which the liquor comprising active agent oxyfluorfen and/or oryzalin and
water-miscible carrier liquid are absorbed at elevated temperature without
agglomeration of the particles. In other words the particles are un-agglomerated
primary particles as distinct from secondary particles formed by agglomeration of
primary powder particles much finer than the secondary particles. Granules formed
without agglomeration are generally less susceptible to formation of fines and are
more effective in delivering herbicide by broadcasting of the solid granules. The solid
carrier may constitute up to 97% by weight of the composition but will typically be up
to 95% by weight of the herbicidal granule composition such as up to 92% w/w or up
to 90% w/w. The solid carrier will generally be at least 65 %w/w of the herbicidal
granule composition such as at least 70 % w/w, at least 75 % w/w or at least 80 %
w/w of the herbicidal granule composition
In one embodiment of the method the mixture comprising carrier liquid and oxyfluorfer
and/or oryzalin is applied to granules in a rotatable drum by pouring the solution onto
granules in the drum and rotating the drum to distribute the liquid among the granules.
In a further aspect there is provided a method of controlling weeds comprising
broadcasting the herbicidal granules herein described onto land in which weed
control is needed. The herbicide may be broadcast as the solid granules onto the site
for weed control and the herbicide released from the granules by water from rainfall,
irrigation or other application of water onto the site on which the granules have been
broadcast.
The invention will now be described with reference to the following examples. It is to
be understood that the examples are provided by way of illustration of the invention
and that they are in no way limiting to the scope of the invention.
EXAMPLES
Excipient chemical descriptions
Substance CAS CHEMICAL NAME other info supplier
hydroxypropoxyl content Made by: Taian ruitai cellulose
7-12% wt, methoxyl Co Ltd, supplied by Redox
Rutocel 60RT6 90043 hydroxypropylmethyl cellulose content 28-30% wt. Chemicals
Bentone SD2 organic derivative of a bentonite clay Elementis specialties
Active gel 150 121990 smectite >87% Unimin
Veegum T 121990 smectite clay (magnesium aluminum silicate) R.T. Vanderbilt Company, Inc.
must be activated before
Cellulon PX microfibrous cellulose use CP Kelco
Microcrystalline cellulose 90046 microcrystalline cellulose Redox Chemicals
Commercial ethyl
cellulose has an ethoxy
content of 43-50% (ref
Ethyl cellulose 90043 cellulose, ethyl ether Merck index) Merck
CMC Carboxymethyl cellulose Lubrizol
Kollidon 30 90038 polyvinyl pyrrolidone BASF
Rhodopol 50MC 111382 xanthan gum Rhodia
Aerosil 200 76319 fumed silica Rhodia
Pemulen TR2-NF acrylates/ c10-30 alkyl acrylate crosspolymer The Lubrizol corporation
Carbopol 90034 Acrylic acid homopolymer The Lubrizol corporation
Agar 90020 agar-agar BDH Chemicals
Gelatine 90008 Davis (from supermarket)
Corn flour 90058 Starch Sigma-aldrich
Kaolin 13327 Aluminum silicate Hydroxide Redox chemicals
HT PRED DRY 13327 Kaolin BASF
PEG 8000 253223 Polyethylene glycol Merck
Airvol 203S 252135 Partially hydrolyzed Polyvinyl Alcohol 87-89% hydrolyzed Air products and chemicals
Butyl diglycol 1125 Diethylene glycol monobutyl ether 162.23 APS chemicals
Butyl diglysolv 1125 Diethylene glycol monobutyl ether 162.23 Huntsman
Attasorb 16/30 LVM 121747 Attapulgite clay/ fuller's earth BASF
Kiln dried bentonite 13029 Montmorillonite Arumpo Bentonite Pty Ltd
Water 77325 Water
Example 1
This Example provides data on the compatibility of various hydrophilic
macromolecules and colloids mixed with a water-miscible carrier liquor, the mixture
comprising a liquor made from 0.63 parts hydrophilic macromolecule or colloid, 2.1
parts oxyfluorfen technical grade (95% purity), 9.4 parts polar liquid blend (said blend
made by adding 2.1 parts of water to 7.3 parts of butyl diicinol = butyl diglysolv =
diethylene glycol monobutyl ether). Compatibility was assessed at 60 C and was
rated as positive if the resultant liquid remained substantially homogeneous over 30
minutes at this temperature.
Hydrophilic macromolecule Compatibility
Rutocel 60RT6 positive
Bentone SD2 positive
Active gel 150 negative
Veegum T negative
Cellulon PX negative
Microcrystalline cellulose negative
Ethyl cellulose positive
Carboxymethyl cellulose negative
Kollidon 30 (polyvinyl pyrrolidone) positive
Rhodopol 50MC negative
Aerosil 200 positive
Permulen TR2-NF negative
Carbopol negative
Agar negative
gelatine negative
Corn flour negative
kaolin negative
Polyethylene glycol (PEG) 8000 positive
Airvol 203S (PVA) negative
Example 2
In this example compositions were prepared by:
(a) making a liquor as in example 1, but with the further addition of 1 part
oryzalin for every 2 parts oxyfluorfen. This oryzalin acted as a colour marker for the
oxyfluorfen crystals. The said liquor included a water-miscible carrier liquor,
oxyfluorfen, oryzalin and a hydrophilic macromolecule or colloid;
(b) heating the resultant material to 60 C with stirring; and
(c) checking that the hot stirred resultant liquor is homogeneous and stable for
at least 30 mins, and if so, adding the hot resultant liquor to kiln dried “plus 300
micron” attapulgite. In this addition step 10.6 parts hot resultant liquor was added to
70 parts attapulgite;
(d) shaking the loaded hot attapulgite in a closed container to uniformity and
then weighing the uniform loaded attapulgite;
(e) allowing the loaded attapulgite to rest at room temperature for 30 minutes
after weighing;
(f) weighing the amount of rested loaded attapulgite retained on a 300 micron
sieve and (g) calculating the percentage of rested loaded material that passed
through the 300 micron sieve.
The above protocol was designed to measure the formation and dislodgement of fine
oxyfluorfen crystals from the loaded attapulgite in storage. Dislodgement of fine
material from the loaded carrier granules was the main failure mechanism for the
formulation.
Hydrophilic Percentage of Comments Colour of final
macromolecule loaded attapulgite product
included in liquor passing through
300 micron sieve
none 0.32 fine material orange
Rutocel 60RT6 0.21 relatively few fines yellow
Bentone SD2 0.54 fine material orange
Ethyl cellulose 0.1 relatively few fines yellow
Kollidon 30 0.1 relatively few fines yellow
Aerosil 200 1.0 fine material orange
Polyethylene glycol 0.32 fine material orange
PEG 8000
Note: The better formulations were noted to have an orange colour after drying and
storage at room temperature.
Example 3
Production of broadcast granule comprising 20g/kg oxyfluorfen and 10g/kg
oryzalin.
Component Concentration (g/kg)
Oxyfluorfen tech (95%) 21.05
Oryzalin tech (95%) 10.53
Rutocel 60RT6 6.30
Butyl Diglysolv 73.15
Water 21.10
Bentonite granules (kiln dried) 867.87
TOTAL 1000
Supplier details:
Butyl glysolv Company: Huntsman
Rutocel 60RT6 Company: Redox Pty Ltd
Bentonite granule (kiln dried) Company: Arumpo Bentonite Pty Ltd
Excipient chemical descriptions
Trade Name Chemical Name CAS No. Function
Hydroxymethyl propyl Hydrophilic
Rutocel 60RT6 90043
cellulose macromolecule
Ethylene glycol monobutyl
Butyl Glysolv 1112 Polar Solvent
ether
Water - 77325 Solvent
Bentonite (kiln dried) Montmorillonite 13029 Porous Carrier
Manufacturing procedure
The following manufacturing procedure has been developed on laboratory scale
equipment.
Method of preparation
Step 1 To a mixing vessel: Add Oxyfluorfen, Oryzalin, Butyl diglysolv and
Rutocel 60RT6.
Step 2 Mix together ingredients using the Dispermat® N1
Step 3 Add water to mixing vessel and mix with Dispermat® N1
Heat mixture to 65ºC to dissolve the active ingredients. A clear orange-
Step 4
coloured solution should result.
Step 5 Pour mixture over bentonite granule and mix until uniform.
Step 6 Allow mixture to dry.
Quality Control
At the completion of the manufacturing process a sample is provided to QC lab and
the following tests completed:
Physical tests Test method Limits
Oryzalin EUR1175 (see example 5) 7.5-12.5 g/kg
Oxyfluorfen EUR1175(see example 5) 15-25 g/kg
Appearance Visual Match to standard
State Visual Match to standard
Colour Visual Match to standard
Odour Olfactory Match to standard
pH MT 75 (CIPAC) 6 - 7 @ 19.7ºC
Bulk density Pour: 0.88 - .92 g/ml
MT 186 (CIPAC)
Tap: 0.92 – 0.96 g/ml
Dust content MT 171 (CIPAC) Non-dusty
Attrition resistance MT 178 (CIPAC) > 98%
Active Ingredient Stability
Active ingredient Limits Ambient Stability
temperature
2 weeks @ 54ºC
Oryzalin 7.5-12.5 g/kg 9.1 9.4
Oxyfluorfen 15-25 g/kg 18.6 20.3
Physical stability
Ambient 2 weeks @ 54ºC
Physical Test Limits
tests method
Appearance Visual n/a Yellow granules Yellow granules
State Visual n/a Solid Solid
Colour Visual n/a Yellow Yellow
Odour Olfactory n/a Characteristic Characteristic
pH MT 75 n/a 6.31 @ 19.7ºC 6.27 @ 19.4ºC
Bulk density n/a Pour: 0.90 g/ml Pour : 0.90 g/ml
MT 186
(CIPAC)
Tap: 0.94 g/ml Tap: 0.92 g/ml
Dust content MT171 Non-dusty
Non-dusty Non-dusty
(CIPAC)
Attrition MT178
> 98% 99.5% 99.6%
resistance
(CIPAC)
Packaging Storage
stability in HDPE No change
No distortions No distortions
(54ºC X on storage
2 weeks)
Example 4
Solubility of active agents at various water ratios with butyl diicinol (TUNG to
supply).
Various ratios of butyldiglycol and water were prepared and sufficient oxyfluorfen
added to provide a 17.3% w/w Oxyfluorfen material.
RATIO of butyl diglycol Solubility at 20ºC Solubility at 60ºC
to water
3.5: 1 (formulation) no Yes
100% water no No
100% butyl diglycol no Yes
1:1 no No
1:3.5 (reversed) no No
1:9 no No
9:1 no yes
Example 5
Determination of Oryzalin and Oxyfluorfen in a Granule by High Performance
Liquid Chromatography.
A 500mg sample of test granules was diluted with acetonitrile to 100ml to give an
assay solution.
Assay was by High Performance Liquid Chromatography using a 5 micron HS C-18
column and UV Vis detection. This gave a relationship between peak area and
analyte concentration which was used to calculate the concentration of oryzalin and
oxyfluorfen from a calibration curve previously derived from the analysis of standard
solutions.
A carefully prepared representative series of five samples was taken from a prepared
liquid formulation as well as a series of four samples ‘spiked’ with a known amount of
standard grade active ingredient.
Each sample was then analysed by RP-HPLC using an Alltech Adsorbosphere HS
(C18) 250mm x 4.6mm column and UV-Vis detection. The grams per kilogram
content of oryzalin and oxyfluorfen was determined from a calibration graph
(response of active ingredient versus concentration of active ingredient) derived from
the analysis of standard solutions.
This method is applicable to the determination of oryzalin and oxyfluorfen in granule
formulations, specifically 10 g/kg and 20 g/kg WG formulations in the matrix of
granules typical of the granules of the invention.
The HPLC was a GBC LC1120 iscoratic pump equipped with a GBC LC1200 UV-Vis
detector, data handling by WinChrom.
The analytical column was an Alltech Adsorbosphere HS (C18) column 250mm (l)
4.6mm (id).
The chromatographic conditions were:
Column: Alltech Adsorbosphere HS (C18) column 250mm (l)
4.6mm (id)
Column Temperature: Ambient
Mobile Phase: Eluent A: 85% acetonitrile : Eluent B: 15% MilliQ water
Injection Volume: 20 ul
Detector wavelength: 280 nm
Retention time: 3.9 min (Oryzalin) 6 min (Oxyfluorfen) @ 1.0mL/min
Chromatogram length: 10 min
Preparation of 10 g/kg oryzalin 20g/kg oxyfluorfen granule samples.
When analysing the granule a sample of approximately 500mg was weighed by
difference into 100ml volumetric flask and its mass was recorded accurately.
The sample was then dispersed with the minimum required amount of Acetonitrile,
made to the mark and inverted to ensure homogeneity.
It was demonstrated that all significant impurities of oryzalin and oxyfluorfen are
separated in the chromatogram. Therefore there was no interference from impurities
in the determination.
Example 6
Bioefficacy and comparison with prior art product.
Summary
At a plant nursery (Botanix) at Carrum Downs, Victoria, two granular products were
applied to the bare soil around the base of ornamental plants in the nursery pots. The
first granular product was designated Crop Culture Tour Ornamental Herbicide, it
contained Oryzalin 10 g/kg and Oxyfluorfen 20 g/kg, was a granule according to the
invention (see example 3). The second granular product also contained Oryzalin 10
g/kg and Oxyfluorfen 20 g/kg , and was designated Rout Ornamental Herbicide. This
second granular product was not a granule according to the invention, and was based
on the use of an aromatic (high-odour) water-insoluble carrier liquid to load active
ingredients into the granule.
The effect on the plant species and the level of weed control were assessed over the
following 4 months.
Results from this trial showed:
Crop Culture Tour Ornamental Herbicide (CC Tour) and Rout Ornamental Herbicide
were effective in controlling the weeds that were present. CC Tour achieved
equivalent levels of weed control to the industry standard.
There was no difference in the level of control when both products were applied at the
same rate.
None of the three plant species, Crepe Myrtle (Lagerstroemia indica), Black Sheoak
Casuarina littoralis or Double Rose Pink Oleander (Nerium oleander) showed signs of
herbicide phytotoxicity from the application of Crop Culture Tour or Rout Ornamental
Herbicide.
Trial Aims:
1. To evaluate Crop Culture Tour for pre-emergent control of various weeds in
nursery pots.
2. To compare Crop Culture Tour to the industry standard, Rout Ornamental
Herbicide.
Methods and Materials
Site Details:
Site
Site Botanix Plant Nursery
Co-operator Carl Soderlund
Contact 0419 117 286
Address Learmonth Road
Carrum Downs, Vic 3201
Soil
Type Loam potting mix pH 7.0
Moisture Good Drainage Good
Tilth Good Organic Matter High
Fertility Good
Trial
Design Randomised Plot Size Single pots Replications 4
Crop Types
Double Rose Pink
Common Name Crepe Myrtle Black Sheoak
Oleander
Species
Lagerstroemia indica Casuarina littoralis Nerium oleander
Site History
Chemicals Used * No chemicals used
Fertiliser Used * Nil
*21 Days prior and post trial application
Plot Size
Crepe Myrtle & Black Sheoak 40cm pots (0.1257 m )
Oleander 30cm pots (0.0707 m )
Application Details
Date: 152009 Time: 1:10 – 3:55 pm
Wind: SW 2-5 km/hr Temp: 11 - 13 C
Humidity: 56 % Cloud Cover: 80 %
Spray Order: 2, 3, 4, 5, 6, 7
Treatments were applied by gentling sprinkling the measured amount of each product
to the surface of the plant pot.
Formulations Used
Active Ingredient and
Code Details Formulation
Concentration
Oryzalin 10 g/kg
Crop Culture Tour
CC Tour granule
Ornamental Herbicide
Oxyfluorfen 20 g/kg
Oryzalin 10 g/kg
Rout Ornamental
Rout granule
Herbicide
Oxyfluorfen 20 g/kg
Treatments
Rate
TTT g per 40cm g per 30cm
Product Trial Code / BN
No. pot pot
kg/ha
1 Untreated -
2 CC Tour 50 0.628 0.354
3 CC Tour 100 1.257 0.707
4 CC Tour 200 2.514 1.414
Rout 50 0.628 0.354
6 Rout 100 1.257 0.707
7 Rout 200 2.514 1.414
Target Weeds
Double
Black
Common Name Scientific Name Crepe Myrtle Rose Pink
Sheoak
Oleander
Chickweed Stellaria media
Cotula Cotula australia
Dandelion Taraxacum officinale
Deadly Nightshade Solanum dulcamara
Flatweed Hypochaeris radicata
Flick Weed (Willow
Epilobium ciliatum
herb)
Fumitory, Pink Fumaria officinalis
Assessment Methods
(i) Plant Phytotoxicity
Each plant in each pot was observed to determine if there were any effects of
pesticide induced phytotoxicity compared to the plants in the untreated pots.
(ii) Weed Control
Weeds present in each plant pot were assessed at 134 days after application.
Analysis
Results were analysed using One-Way Analysis of Variance and where the Fcalc was
significant (P<0.05) mean plot values were compared using LSD, means sharing
common postscripts are not significantly different (LSD test, P<0.05).
Because the plant numbers were low, analyses were conducted on the total plants
per pot.
Analyses were conducted both including and excluding the untreated pots.
Assessment & Assessment Timings
Assessment Days After Assessment Type
Treatment
Number
1 35 Plant Phytotoxicity
2 76 Plant Phytotoxicity
3 134 Plant Phytotoxicity & Weed Counts
RESULTS
Efficacy
Weeds present in each plant pot were assessed 134 days after application (134DAT).
The weeds present varied for each of the plant species, Section 2.5, and although the
numbers were low this is a function of the pot size.
The weeds present are shown in tables 1, 2 and 3 below.
Table 1. Weeds per Pot - Black Sheoak (Casuarina littoralis) - 134 DAT
Deadly
Dandelion Flatweed Total
Weed Nightshade
Treatments
1. Untreated 3.5 2.0 1.8 7.3 a
2. CC Tour – 50 kg/ha 0.3 0.5 0.3 1.0 b ab
3. CC Tour – 100 kg/ha 0.3 0.0 0.5 0.8 b b
4. CC Tour - 200 kg/ha 0.5 0.0 0.0 0.5 b b
. Rout – 50 kg/ha 1.0 0.8 0.8 2.5 b a
6. Rout – 100 kg/ha 0.3 0.3 0.5 1.0 b ab
7. Rout – 200 kg/ha 0.3 0.0 0.0 0.3 b b
LSD (p<0.05) 2.683 1.645
Table 2. Weeds per Pot – Crepe Myrtle (Lagerstroemia indica) - 134 DAT
Weed Chickweed Cotula
Treatments
1. Untreated 2.5 3.5
2. CC Tour – 50 kg/ha 0.5 1.8
3. CC Tour – 100 kg/ha 0.3 0.0
4. CC Tour - 200 kg/ha 0.0 0.0
. Rout – 50 kg/ha 0.8 1.8
6. Rout – 100 kg/ha 0.3 0.5
7. Rout – 200 kg/ha 0.3 0.0
Weed Dandelion Flick Weed Total
Treatments
1. Untreated 1.8 2.5 10.3 a
2. CC Tour – 50 kg/ha 0.3 0.3 2.8 b ab
3. CC Tour – 100 kg/ha 0.3 0.3 0.8 b ab
4. CC Tour - 200 kg/ha 0.0 0.0 0.0 b b
. Rout – 50 kg/ha 0.3 0.5 3.3 b a
6. Rout – 100 kg/ha 0.3 0.0 1.0 b ab
7. Rout – 200 kg/ha 0.0 0.0 0.3 b b
LSD (p<0.05) 3.717 1.645
Table 3. Weeds per Pot - Double Rose Pink Oleander (Nerium oleander)- 134 DAT
Weed Chickweed Dandelion
Treatments
1. Untreated
2.0 1.5
2. CC Tour – 50 kg/ha
0.3 0.0
3. CC Tour – 100 kg/ha 0.3 0.0
4. CC Tour - 200 kg/ha
0.0 0.0
. Rout – 50 kg/ha
0.5 0.3
6. Rout – 100 kg/ha
0.3 0.0
7. Rout – 200 kg/ha
0.3 0.0
Weed Flick Weed Fumitory, Pink Total
Treatments
1. Untreated
1.5 2.5 7.5 a
2. CC Tour – 50 kg/ha
0.3 0.0 0.5 b
3. CC Tour – 100 kg/ha
0.3 0.0 0.5 b
4. CC Tour - 200 kg/ha
0.0 0.0 0.0 b
. Rout – 50 kg/ha
0.3 0.5 1.5 b
6. Rout – 100 kg/ha
0.3 0.0 0.5 b
7. Rout – 200 kg/ha
0.0 0.0 0.3 b
LSD (p<0.05) 2.816 NS
DISCUSSION
Weed Counts
For each plant species the weeds present in the pot were significantly reduced by the
addition of Crop Culture Tour or Rout, Tables 1, 2 & 3.
Equal rates of CC Tour and Rout gave the same (statistically) level of weed control in
each of three different plant species pots, Tables 1, 2 & 3.
For the weeds present in the Black Sheoak pots, Dandelion, Deadly Nightshade and
Flatweed, the low rate of Rout although not significantly different to the low rate of CC
Tour and 100 kg/ha Rout was significantly inferior to the 100 and 200 kg/ha rates of
CC Tour and Rout at 200 kg/ha, Table 1.
In the Crepe Myrtle pots, the weeds present; Chickweed, Cotula, Dandelion and
Flatweed, were controlled least by the low rate of Rout, which was not significantly
different to the CC Tour at 50 and 100 kg/ha, and Rout at 100 kg/ha, but was
significantly inferior to the high rate, 200 kg/ha of both CC Tour and Rout, Table 2.
For the weeds present in the Pink Oleander pots, Chickweed, Dandelion, Flick Weed
and Pink Fumitory, there was no difference in the weed control obtained with any rate
of CC Tour or Rout, although all were significantly superior to the untreated pots,
Table 3.
In summary, Crop Culture Tour Ornamental Herbicide and Rout Ornamental
Herbicide were effective in controlling the weeds in pots that contained three
ornamental plant species.
There was no difference in the level of control when both products were applied at the
same rate.
Plant Phytotoxicity
At each assessment there was no visible effect of the three plant species in either
product at all rates compared to the plants in the untreated pots.
CONCLUSIONS
1. CC Tour provided effective control of a range of grass and broadleaf weeds
present in this trial.
2. CC Tour achieved equivalent levels of weed control to the industry standard, Rout
Ornamental Herbicide, when applied at the same rate of product.
3. None of the three plant species, Crepe Myrtle (Lagerstroemia indica), Black
Sheoak Casuarina littoralis or Double Rose Pink Oleander (Nerium oleander)
showed signs of herbicide phytotoxicity from the application of Crop Culture Tour
or Rout Ornamental Herbicide.
Assessment Data
Black Sheoak
26-Nov-10 134DAT
Dandelion
Rep 1 2 3 4 total mean
1. Untreated 2.0 3.0 4.0 5.0 14 3.5
2. CC Tour – 50 kg/ha 1.0 0.0 0.0 0.0 1 0.3
3. CC Tour – 100
kg/ha 0.0 1.0 0.0 0.0 1 0.3
4. CC Tour - 200 kg/ha 0.0 0.0 0.0 2.0 2 0.5
. Rout – 50 kg/ha 2.0 1.0 1.0 0.0 4 1.0
6. Rout – 100 kg/ha 0.0 0.0 1.0 0.0 1 0.3
7. Rout – 200 kg/ha 0.0 1.0 0.0 0.0 1 0.3
Deadly Nightshade
Rep 1 2 3 4 total mean
1. Untreated 1.0 3.0 1.0 3.0 8 2.0
2. CC Tour – 50 kg/ha 0.0 1.0 0.0 1.0 2 0.5
3. CC Tour – 100
kg/ha 0.0 0.0 0.0 0.0 0 0.0
4. CC Tour - 200 kg/ha 0.0 0.0 0.0 0.0 0 0.0
. Rout – 50 kg/ha 1.0 0.0 1.0 1.0 3 0.8
6. Rout – 100 kg/ha 0.0 1.0 0.0 0.0 1 0.3
7. Rout – 200 kg/ha 0.0 0.0 0.0 0.0 0 0.0
Flatweed
Rep 1 2 3 4 total mean
1. Untreated 1.0 1.0 2.0 3.0 7 1.8
2. CC Tour – 50 kg/ha 1.0 0.0 0.0 0.0 1 0.3
3. CC Tour – 100
kg/ha 1.0 0.0 1.0 0.0 2 0.5
4. CC Tour - 200 kg/ha 0.0 0.0 0.0 0.0 0 0.0
. Rout – 50 kg/ha 0.0 1.0 1.0 1.0 3 0.8
6. Rout – 100 kg/ha 1.0 0.0 1.0 0.0 2 0.5
7. Rout – 200 kg/ha 0.0 0.0 0.0 0.0 0 0.0
Total Weeds
Rep 1 2 3 4 total mean
1. Untreated 4.0 7.0 7.0 11.0 29 7.3
2. CC Tour – 50 kg/ha 2.0 1.0 0.0 1.0 4 1.0
3. CC Tour – 100
kg/ha 1.0 1.0 1.0 0.0 3 0.8
4. CC Tour - 200 kg/ha 0.0 0.0 0.0 2.0 2 0.5
. Rout – 50 kg/ha 3.0 2.0 3.0 2.0 10 2.5
6. Rout – 100 kg/ha 1.0 1.0 2.0 0.0 4 1.0
7. Rout – 200 kg/ha 0.0 1.0 0.0 0.0 1 0.3
Crepe Myrtle
26-Nov-10 134DAT
Chickweed
Rep 1 2 3 4 total mean
1. Untreated 1.0 4.0 4.0 1.0 10 2.5
2. CC Tour – 50 kg/ha 1.0 0.0 0.0 1.0 2 0.5
3. CC Tour – 100
kg/ha 0.0 1.0 0.0 0.0 1 0.3
4. CC Tour - 200 kg/ha 0.0 0.0 0.0 0.0 0 0.0
. Rout – 50 kg/ha 1.0 0.0 0.0 2.0 3 0.8
6. Rout – 100 kg/ha 0.0 0.0 1.0 0.0 1 0.3
7. Rout – 200 kg/ha 0.0 1.0 0.0 0.0 1 0.3
Cotula
Rep 1 2 3 4 total mean
1. Untreated 5.0 5.0 3.0 1.0 14 3.5
2. CC Tour – 50 kg/ha 2.0 1.0 2.0 2.0 7 1.8
3. CC Tour – 100
kg/ha 0.0 0.0 0.0 0.0 0 0.0
4. CC Tour - 200 kg/ha 0.0 0.0 0.0 0.0 0 0.0
. Rout – 50 kg/ha 3.0 1.0 1.0 2.0 7 1.8
6. Rout – 100 kg/ha 0.0 0.0 2.0 0.0 2 0.5
7. Rout – 200 kg/ha 0.0 0.0 0.0 0.0 0 0.0
Dandelion
Rep 1 2 3 4 total mean
1. Untreated 1.0 1.0 2.0 3.0 7 1.8
2. CC Tour – 50 kg/ha 1.0 0.0 0.0 0.0 1 0.3
3. CC Tour – 100
kg/ha 0.0 0.0 1.0 0.0 1 0.3
4. CC Tour - 200 kg/ha 0.0 0.0 0.0 0.0 0 0.0
. Rout – 50 kg/ha 0.0 1.0 0.0 0.0 1 0.3
6. Rout – 100 kg/ha 0.0 0.0 1.0 0.0 1 0.3
7. Rout – 200 kg/ha 0.0 0.0 0.0 0.0 0 0.0
Flick Weed
Rep 1 2 3 4 total mean
1. Untreated 4.0 3.0 3.0 0.0 10 2.5
2. CC Tour – 50 kg/ha 0.0 0.0 1.0 0.0 1 0.3
3. CC Tour – 100
kg/ha 0.0 1.0 0.0 0.0 1 0.3
4. CC Tour - 200 kg/ha 0.0 0.0 0.0 0.0 0 0.0
. Rout – 50 kg/ha 1.0 0.0 1.0 0.0 2 0.5
6. Rout – 100 kg/ha 0.0 0.0 0.0 0.0 0 0.0
7. Rout – 200 kg/ha 0.0 0.0 0.0 0.0 0 0.0
Total Weeds
Rep 1 2 3 4 total mean
1. Untreated 11.0 13.0 12.0 5.0 41 10.3
2. CC Tour – 50 kg/ha 4.0 1.0 3.0 3.0 11 2.8
3. CC Tour – 100
kg/ha 0.0 2.0 1.0 0.0 3 0.8
4. CC Tour - 200 kg/ha 0.0 0.0 0.0 0.0 0 0.0
. Rout – 50 kg/ha 5.0 2.0 2.0 4.0 13 3.3
6. Rout – 100 kg/ha 0.0 0.0 4.0 0.0 4 1.0
7. Rout – 200 kg/ha 0.0 1.0 0.0 0.0 1 0.3
Oleander
26-Nov-10 134DAT
Chickweed
Rep 1 2 3 4 total mean
1. Untreated 3.0 0.0 4.0 1.0 8 2.0
2. CC Tour – 50 kg/ha 1.0 0.0 0.0 0.0 1 0.3
3. CC Tour – 100 kg/ha 0.0 1.0 0.0 0.0 1 0.3
4. CC Tour - 200 kg/ha 0.0 0.0 0.0 0.0 0 0.0
. Rout – 50 kg/ha 0.0 0.0 0.0 2.0 2 0.5
6. Rout – 100 kg/ha 0.0 0.0 1.0 0.0 1 0.3
7. Rout – 200 kg/ha 0.0 1.0 0.0 0.0 1 0.3
Dandelion
Rep 1 2 3 4 total mean
1. Untreated 1.0 3.0 1.0 1.0 6 1.5
2. CC Tour – 50 kg/ha 0.0 0.0 0.0 0.0 0 0.0
3. CC Tour – 100 kg/ha 0.0 0.0 0.0 0.0 0 0.0
4. CC Tour - 200 kg/ha 0.0 0.0 0.0 0.0 0 0.0
. Rout – 50 kg/ha 0.0 0.0 1.0 0.0 1 0.3
6. Rout – 100 kg/ha 0.0 0.0 0.0 0.0 0 0.0
7. Rout – 200 kg/ha 0.0 0.0 0.0 0.0 0 0.0
Flick Weed
Rep 1 2 3 4 total mean
1. Untreated 1.0 2.0 3.0 0.0 6 1.5
2. CC Tour – 50 kg/ha 1.0 0.0 0.0 0.0 1 0.3
3. CC Tour – 100 kg/ha 0.0 0.0 1.0 0.0 1 0.3
4. CC Tour - 200 kg/ha 0.0 0.0 0.0 0.0 0 0.0
. Rout – 50 kg/ha 0.0 1.0 0.0 0.0 1 0.3
6. Rout – 100 kg/ha 0.0 0.0 1.0 0.0 1 0.3
7. Rout – 200 kg/ha 0.0 0.0 0.0 0.0 0 0.0
Fumitory, Pink
Rep 1 2 3 4 total mean
1. Untreated 4.0 3.0 2.0 1.0 10 2.5
2. CC Tour – 50 kg/ha 0.0 0.0 0.0 0.0 0 0.0
3. CC Tour – 100 kg/ha 0.0 0.0 0.0 0.0 0 0.0
4. CC Tour - 200 kg/ha 0.0 0.0 0.0 0.0 0 0.0
. Rout – 50 kg/ha 1.0 0.0 1.0 0.0 2 0.5
6. Rout – 100 kg/ha 0.0 0.0 0.0 0.0 0 0.0
7. Rout – 200 kg/ha 0.0 0.0 0.0 0.0 0 0.0
Total Weeds
Rep 1 2 3 4 total mean
1. Untreated 9.0 8.0 10.0 3.0 30 7.5
2. CC Tour – 50 kg/ha 2.0 0.0 0.0 0.0 2 0.5
3. CC Tour – 100 kg/ha 0.0 1.0 1.0 0.0 2 0.5
4. CC Tour - 200 kg/ha 0.0 0.0 0.0 0.0 0 0.0
. Rout – 50 kg/ha 1.0 1.0 2.0 2.0 6 1.5
6. Rout – 100 kg/ha 0.0 0.0 2.0 0.0 2 0.5
7. Rout – 200 kg/ha 0.0 1.0 0.0 0.0 1 0.3
Example 7
The following granule compositions of the invention were prepared using polyethylene
glycols as the water-miscible carrier liquid.
Granule (a)
Component Concentration (g/kg)
Oxyfluorfen (96%) 21.05
Oryzalin (95%) 10.53
PEG 200 100
Attapulgite 868.42
TOTAL 1000
Granule (b)
Component Concentration (g/kg)
Oxyfluorfen (96%) 21.05
Oryzalin (95%) 10.53
PEG 300 100
Attapulgite 868.42
TOTAL 1000
Granule (c)
Component Concentration (g/kg)
Oxyfluorfen (96%) 21.05
Oryzalin (95%) 10.53
PEG 600 100
Attapulgite 868.42
TOTAL 1000
Granule (d)
Component Concentration (g/kg)
Oxyfluorfen (96%) 21.05
Oryzalin (95%) 10.53
PEG 200 70
PEG 600 70
Attapulgite 828.42
TOTAL 1000
Results:
Formulation number Results Liquid Concentrate
Dull yellow granule Recrystallizes at room temp.
Dull yellow granule Recrystallizes at room temp.
c Yellow granule Recrystallizes at room temp.
d Dull yellow granule Partial re-crystallization at
room temp. Slow process.
Over time granules a to d were found to form fine dust material which makes these
compositions less suited to long term storage and handling than the composition of
Example 3.
Claims (39)
1. A herbicidal broadcast granule comprising at least one of oxyfluorfen and oryzalin in solid form in an amount of no more than 8% by weight oxyfluorfen and no more than 8% by weight oryzalin based on the total granule and a water-miscible carrier liquid in which the at least one of oxyfluorfen and oryzalin is soluble in an amount of at least 8% w/w at a temperature of 60 C.
2. A herbicidal broadcast granule comprising oxyfluorfen in solid form in an amount of up to 8% by weight/weight oxyfluorfen based on the total granule weight and a water-miscible carrier liquid in which oxyfluorfen is soluble in an amount of at least 8% weight/weight at a temperature of 60ºC.
3. A herbicidal broadcast granule according to claim 1 or claim 2 wherein the solid form is a precipitate.
4. A herbicidal broadcast granule according to claim 1 or claim 2 wherein the solid form is a crystalline precipitate.
5. A herbicidal broadcast granule according to any one of claims 1 to 4 wherein oxyfluorfen is present in an amount of from 0.5 % w/w to 5 % w/w of the granule composition and oryzalin is present in an amount of from 0.5 % w/w to 4 % w/w of the granule composition.
6. A herbicidal broadcast granule according to any one of claims 1 to 5 wherein the water-miscible carrier liquid comprises water-miscible organic compound and water in a volume/volume ratio of water-miscible organic compound to water in the range of from 10:1 to 1:1.
7. A herbicidal broadcast granule according to any one of the previous claims comprising a hydrophilic tackifying macromolecule.
8. A herbicidal broadcast granule according to claim 7 wherein the hydrophilic tackifying macromolecule is selected from the group consisting of polyvinyl pyrrolidine and cellulosic polymers and polyethylene glycols.
9. A herbcidal broadcast granule according to any one of the previous claims wherein the oxyfluorfen is crystallised from a solution of the water-miscible carrier liquid absorbed into the granule at elevated temperature.
10. A herbicidal broadcast granule according to any one of the previous claims wherein oryzalin is present and is crystallised from solution of the water- miscible carrier liquid absorbed into the granule at elevated temperature.
11. A herbicidal broadcast granule according to any one of the previous claims wherein the oxyfluorfen has a solubility in the water-miscible carrier liquid of no more than 10% by weight/weight at 20 C.
12. A herbicidal broadcast granule according to claim 11 wherein the oxyfluorfen has a solubility in the water-miscible carrier liquid of no more than 5% by weight/weight at 20 C.
13. A herbicidal broadcast granule according to any one of the previous claims wherein the water-miscible carrier liquid is present in an amount of from 2% to 15 % by weight based on the total weight of the granule composition.
14. A herbicidal broadcast granule according to any one of the previous claims wherein the water-miscible carrier liquid comprises a water-miscible organic compound which is miscible in a 1 : 1 volume ratio with water at 20 C.
15. A herbicidal broadcast granule according to any one of the previous claims wherein the granules are of size in the range of from 0.2mm to 4mm.
16. A herbicidal broadcast granule according to claim 15 wherein the granules are of size in the range of from 0.5mm to 1.5mm.
17. A herbicidal broadcast granule according to any one of the previous claims wherein the water-miscible carrier liquid comprises a water-miscible organic compound selected from the group consisting of glycol ethers and polyalkylene glycols.
18. A herbicidal broadcast granule according to claim 17 wherein the water- miscible organic compound is selected from the group consisting of mono-(C to C alkyl)ethers of di- or tri-(C to C alkylene)glycols and polyethylene 6 2 4 glycols.
19. A herbicidal broadcast granule according to claim 17 wherein the water- miscible organic compound is selected from the group consisting of diethylene glycol mono alkyl ethers and triethylene glycol mono alkyl ethers wherein the alkyl is selected from methyl, ethyl, propyl and butyl.
20. A herbicidal broadcast granule according to claim 7 wherein the weight ratio of hydrophillic tackifying agent to water-miscible carrier liquid is in a weight by weight ratio in the range of from 0.03 to 0.15.
21. A herbicidal broadcast granule according to any one of the previous claims wherein the granule is a non-agglomerated granule.
22. A method of forming a herbicidal broadcast granule comprising at least one of oxyfluorfen and oryzalin in crystalline solid form in an amount of no more than 8% by weight oxyfluorfen and no more than 8% oryzalin based on the total granule weight, the method comprising: providing a solution of at least one of oxyfluorfen and oryzalin in a water- miscible carrier liquid at an elevated temperature of at least 40 C, in which said at least one of oxyfluorfen and oryzalin is soluble in an amount of at least 8% by weight at a temperature of 60 C based on the weight of water-miscible carrier liquid; wherein the water-miscible carrier liquid comprises a water-miscible organic compound and water in an amount of at least 10% on a weight by weight basis of the water-miscible carrier liquid; applying the solution at an elevated temperature to absorbent clay granules to provide active herbicide loaded granules having a loading of at least one of oxyfluorfen and oryzalin of up to 8% by weight of the total weight of loaded granules; and cooling the granules to precipitate at least one of oxyfluorfen and oryzalin within the granules.
23. The method according to claim 22 wherein the elevated temperature is at least 50 C and wherein said at least one of oxyfluorfen and oryzalin is soluble in an amount of at least 15% by weight at a temperature 60 C based on the weight of water-miscible carrier liquid.
24. The method according to claim 22 or claim 23 wherein the elevated temperature is at least 60 C.
25. A method of forming an oxyfluorfen broadcast granule comprising oxyfluorfen in crystalline solid form in an amount up to 8% by weight oxyfluorfen based on the total granule weight, the method comprising: providing a solution of oxyfluorfen in a water-miscible carrier liquid at an elevated temperature of at least 50 C, in which oxyfluorfen is soluble in an amount of at least 25% by weight oxyfluorfen at a temperature of 60ºC based on the weight of water-miscible carrier liquid; and wherein the water-miscible carrier liquid comprises a water-miscible organic compound and water in an amount of at least 10% on a weight by weight basis of the water-miscible carrier liquid; and wherein the solubility of oxyfluorfen in the water-miscible carrier liquid is no more than 5% w/w at 20ºC by weight oxyfluorfen based on the weight of the water miscible carrier liquid; and applying the solution at an elevated temperature of at least 50 C to clay granules to provide active loaded granules having a loading of oxyfluorfen of up to 8% oxyfluorfen by weight of the total active loaded granules absorbed into the granules; and cooling the granules to precipitate oxyfluorfen within the granules.
26. A method of according to any one of claims 22 to 25 wherein the water- miscible carrier liquid comprises volume/volume ratio of water-miscible organic compound to water in the range of from 10:1 to 1:1 and wherein the water-miscible organic compound is used in a ratio with water in which it is miscible at the temperature at which the solution is applied.
27. A method according to any one of claims 22 to 26 wherein the water-miscible organic compound is selected from the group consisting of C to C alkyl mono ethers of di and tri C to C alkylene glycols and polyethylene glycols.
28. A method according to claim 27 wherein the water-miscible organic compound is selected from the group consisting of diethylene glycol mono alkyl ethers and triethylene glycol mono alkyl ethers wherein the alkyl is selected from methyl, ethyl, propyl and butyl and polyethylene glycols of molecular weight 200 to 10,000.
29. A method according to any one of claims 22 to 28 wherein the solution applied to the granular composition comprises in the range of from 10% to 40% by weight oxyfluorfen.
30. A method according to any one of claims 22 to 29 wherein the solution applied to the granular composition comprises oryzalin in an amount in the range of from 5% w/w to 20% w/w.
31. A method according to any one of claims 22 to 30 wherein the loading of oxyfluorfen on the granules is from 0.5% to 5% w/w.
32. A method according to any one of claims 22 to 31 wherein the solution further comprises a hydrophillic polymer selected from the group consisting of cellulose polymers polyvinyl pyrolidone and polyethylene glycols.
33. A method according to any one of claims 22 to 32 wherein the solution further comprises oryzalin in an amount of from 0.5% w/w to 4% w/w of the granule composition.
34. A method according to any one of claims 22 to 33 applied to granules in a rotatable drum by pouring the solution on to granules in the drum and rotating the drum to distribute the liquid among the granules.
35. A method according to any one of claims 22 to 34 wherein the granules combined with the solution are formed of clay selected from the group consisting of attapulgite, bentonite and mixtures thereof.
36. A method according to any one of claims 22 to 35 wherein the granules to which the solution is applied are of size in the range of from 0.5 to 1.5mm.
37. A method according to any one claims 22 to 36 wherein the granule is a non- agglomerated granule.
38. The herbicidal broadcast granule according to any one of claims 1 to 21, substantially as hereinbefore described with reference to any of the Examples.
39. The method according to any one of claims 22 to 37, substantially as hereinbefore described with reference to any of the Examples.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2011901213 | 2011-04-01 | ||
AU2011901213A AU2011901213A0 (en) | 2011-04-01 | Granule composition containing herbicide and method for preparation thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
NZ599091A NZ599091A (en) | 2013-02-22 |
NZ599091B true NZ599091B (en) | 2013-05-23 |
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