WO2015200662A1 - Controlled-release sulfentrazone to safen plants - Google Patents
Controlled-release sulfentrazone to safen plants Download PDFInfo
- Publication number
- WO2015200662A1 WO2015200662A1 PCT/US2015/037740 US2015037740W WO2015200662A1 WO 2015200662 A1 WO2015200662 A1 WO 2015200662A1 US 2015037740 W US2015037740 W US 2015037740W WO 2015200662 A1 WO2015200662 A1 WO 2015200662A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formulation
- group
- sulfentrazone
- controlled
- release
- Prior art date
Links
- 238000013270 controlled release Methods 0.000 title claims abstract description 52
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 title claims description 83
- 239000000203 mixture Substances 0.000 claims abstract description 113
- 238000009472 formulation Methods 0.000 claims abstract description 78
- 239000002245 particle Substances 0.000 claims abstract description 76
- 239000011248 coating agent Substances 0.000 claims abstract description 53
- 238000000576 coating method Methods 0.000 claims abstract description 53
- 239000008187 granular material Substances 0.000 claims abstract description 45
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 44
- 239000004480 active ingredient Substances 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 28
- 239000007787 solid Substances 0.000 claims abstract description 13
- 231100000674 Phytotoxicity Toxicity 0.000 claims abstract description 10
- 239000004927 clay Substances 0.000 claims description 51
- 239000001993 wax Substances 0.000 claims description 41
- 239000003921 oil Substances 0.000 claims description 37
- 235000019198 oils Nutrition 0.000 claims description 37
- 108020001991 Protoporphyrinogen Oxidase Proteins 0.000 claims description 27
- 102000005135 Protoporphyrinogen oxidase Human genes 0.000 claims description 27
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 22
- 239000002480 mineral oil Substances 0.000 claims description 22
- 239000003112 inhibitor Substances 0.000 claims description 21
- 239000004203 carnauba wax Substances 0.000 claims description 17
- 235000013869 carnauba wax Nutrition 0.000 claims description 17
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 17
- 235000021388 linseed oil Nutrition 0.000 claims description 16
- 239000000944 linseed oil Substances 0.000 claims description 16
- 235000010446 mineral oil Nutrition 0.000 claims description 14
- -1 cyclic imide Chemical class 0.000 claims description 13
- 235000017060 Arachis glabrata Nutrition 0.000 claims description 12
- 244000105624 Arachis hypogaea Species 0.000 claims description 12
- 235000010777 Arachis hypogaea Nutrition 0.000 claims description 12
- 235000018262 Arachis monticola Nutrition 0.000 claims description 12
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 12
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 12
- 235000020232 peanut Nutrition 0.000 claims description 12
- 235000013871 bee wax Nutrition 0.000 claims description 11
- 239000012166 beeswax Substances 0.000 claims description 11
- 239000000377 silicon dioxide Substances 0.000 claims description 11
- 239000005995 Aluminium silicate Substances 0.000 claims description 9
- 235000012211 aluminium silicate Nutrition 0.000 claims description 9
- 229960000892 attapulgite Drugs 0.000 claims description 9
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 9
- 229910052625 palygorskite Inorganic materials 0.000 claims description 9
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 7
- 239000008158 vegetable oil Substances 0.000 claims description 7
- NYHLMHAKWBUZDY-QMMMGPOBSA-N (2s)-2-[2-chloro-5-[2-chloro-4-(trifluoromethyl)phenoxy]benzoyl]oxypropanoic acid Chemical compound C1=C(Cl)C(C(=O)O[C@@H](C)C(O)=O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NYHLMHAKWBUZDY-QMMMGPOBSA-N 0.000 claims description 6
- KNGWEAQJZJKFLI-UHFFFAOYSA-N 2,2-dimethyl-4h-1,3-benzodioxine-6-carbaldehyde Chemical compound O=CC1=CC=C2OC(C)(C)OCC2=C1 KNGWEAQJZJKFLI-UHFFFAOYSA-N 0.000 claims description 6
- OVQJTYOXWVHPTA-UHFFFAOYSA-N 2-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-nitropyrazol-3-amine Chemical compound NC1=C([N+]([O-])=O)C=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl OVQJTYOXWVHPTA-UHFFFAOYSA-N 0.000 claims description 6
- ONNQFZOZHDEENE-UHFFFAOYSA-N 2-[5-(but-3-yn-2-yloxy)-4-chloro-2-fluorophenyl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione Chemical compound C1=C(Cl)C(OC(C)C#C)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F ONNQFZOZHDEENE-UHFFFAOYSA-N 0.000 claims description 6
- ZGGSVBWJVIXBHV-UHFFFAOYSA-N 2-chloro-1-(4-nitrophenoxy)-4-(trifluoromethyl)benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(C(F)(F)F)C=C1Cl ZGGSVBWJVIXBHV-UHFFFAOYSA-N 0.000 claims description 6
- WYJOEQHHWHAJRB-UHFFFAOYSA-N 3-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenoxy]oxolane Chemical compound C1=C(OC2COCC2)C([N+](=O)[O-])=CC=C1OC1=CC=C(C(F)(F)F)C=C1Cl WYJOEQHHWHAJRB-UHFFFAOYSA-N 0.000 claims description 6
- DVOODWOZJVJKQR-UHFFFAOYSA-N 5-tert-butyl-3-(2,4-dichloro-5-prop-2-ynoxyphenyl)-1,3,4-oxadiazol-2-one Chemical group O=C1OC(C(C)(C)C)=NN1C1=CC(OCC#C)=C(Cl)C=C1Cl DVOODWOZJVJKQR-UHFFFAOYSA-N 0.000 claims description 6
- HZKBYBNLTLVSPX-UHFFFAOYSA-N 6-[(6,6-dimethyl-5,7-dihydropyrrolo[2,1-c][1,2,4]thiadiazol-3-ylidene)amino]-7-fluoro-4-prop-2-ynyl-1,4-benzoxazin-3-one Chemical compound C#CCN1C(=O)COC(C=C2F)=C1C=C2N=C1SN=C2CC(C)(C)CN21 HZKBYBNLTLVSPX-UHFFFAOYSA-N 0.000 claims description 6
- 239000002890 Aclonifen Substances 0.000 claims description 6
- 239000005484 Bifenox Substances 0.000 claims description 6
- 239000005492 Carfentrazone-ethyl Substances 0.000 claims description 6
- IRECWLYBCAZIJM-UHFFFAOYSA-N Flumiclorac pentyl Chemical group C1=C(Cl)C(OCC(=O)OCCCCC)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F IRECWLYBCAZIJM-UHFFFAOYSA-N 0.000 claims description 6
- HHMCAJWVGYGUEF-UHFFFAOYSA-N Fluorodifen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O HHMCAJWVGYGUEF-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- 239000005588 Oxadiazon Substances 0.000 claims description 6
- CHNUNORXWHYHNE-UHFFFAOYSA-N Oxadiazon Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(OC(=N2)C(C)(C)C)=O)=C1Cl CHNUNORXWHYHNE-UHFFFAOYSA-N 0.000 claims description 6
- 239000005590 Oxyfluorfen Substances 0.000 claims description 6
- 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 description 6
- NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical group C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 claims description 6
- DDBMQDADIHOWIC-UHFFFAOYSA-N aclonifen Chemical compound C1=C([N+]([O-])=O)C(N)=C(Cl)C(OC=2C=CC=CC=2)=C1 DDBMQDADIHOWIC-UHFFFAOYSA-N 0.000 claims description 6
- XOEMATDHVZOBSG-UHFFFAOYSA-N azafenidin Chemical compound C1=C(OCC#C)C(Cl)=CC(Cl)=C1N1C(=O)N2CCCCC2=N1 XOEMATDHVZOBSG-UHFFFAOYSA-N 0.000 claims description 6
- JEDYYFXHPAIBGR-UHFFFAOYSA-N butafenacil Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC=C(Cl)C(C(=O)OC(C)(C)C(=O)OCC=C)=C1 JEDYYFXHPAIBGR-UHFFFAOYSA-N 0.000 claims description 6
- NNKKTZOEKDFTBU-YBEGLDIGSA-N cinidon ethyl Chemical compound C1=C(Cl)C(/C=C(\Cl)C(=O)OCC)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1 NNKKTZOEKDFTBU-YBEGLDIGSA-N 0.000 claims description 6
- 239000007931 coated granule Substances 0.000 claims description 6
- MLKCGVHIFJBRCD-UHFFFAOYSA-N ethyl 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoate Chemical group C1=C(Cl)C(CC(Cl)C(=O)OCC)=CC(N2C(N(C(F)F)C(C)=N2)=O)=C1F MLKCGVHIFJBRCD-UHFFFAOYSA-N 0.000 claims description 6
- FOUWCSDKDDHKQP-UHFFFAOYSA-N flumioxazin Chemical compound FC1=CC=2OCC(=O)N(CC#C)C=2C=C1N(C1=O)C(=O)C2=C1CCCC2 FOUWCSDKDDHKQP-UHFFFAOYSA-N 0.000 claims description 6
- ZCNQYNHDVRPZIH-UHFFFAOYSA-N fluthiacet-methyl Chemical group C1=C(Cl)C(SCC(=O)OC)=CC(N=C2N3CCCCN3C(=O)S2)=C1F ZCNQYNHDVRPZIH-UHFFFAOYSA-N 0.000 claims description 6
- BGZZWXTVIYUUEY-UHFFFAOYSA-N fomesafen Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)C)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 BGZZWXTVIYUUEY-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 claims description 6
- OYJMHAFVOZPIOY-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1 OYJMHAFVOZPIOY-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 244000038559 crop plants Species 0.000 claims description 5
- 235000010523 Cicer arietinum Nutrition 0.000 claims description 4
- 244000045195 Cicer arietinum Species 0.000 claims description 4
- 244000068988 Glycine max Species 0.000 claims description 4
- 235000010469 Glycine max Nutrition 0.000 claims description 4
- 244000061176 Nicotiana tabacum Species 0.000 claims description 4
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 4
- 240000007594 Oryza sativa Species 0.000 claims description 4
- 235000007164 Oryza sativa Nutrition 0.000 claims description 4
- 240000000111 Saccharum officinarum Species 0.000 claims description 4
- 235000007201 Saccharum officinarum Nutrition 0.000 claims description 4
- 239000011247 coating layer Substances 0.000 claims description 4
- 235000009566 rice Nutrition 0.000 claims description 4
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- 230000002363 herbicidal effect Effects 0.000 description 22
- 239000004009 herbicide Substances 0.000 description 18
- 241000196324 Embryophyta Species 0.000 description 10
- 239000002689 soil Substances 0.000 description 10
- 238000002156 mixing Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 description 7
- 239000012876 carrier material Substances 0.000 description 7
- 239000002250 absorbent Substances 0.000 description 5
- 230000002745 absorbent Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 102100026816 DNA-dependent metalloprotease SPRTN Human genes 0.000 description 4
- 101710175461 DNA-dependent metalloprotease SPRTN Proteins 0.000 description 4
- 239000000969 carrier Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- IPPAUTOBDWNELX-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical group C1=C([N+]([O-])=O)C(C(=O)OCC(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 IPPAUTOBDWNELX-UHFFFAOYSA-N 0.000 description 2
- RUPBZQFQVRMKDG-UHFFFAOYSA-M Didecyldimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(C)CCCCCCCCCC RUPBZQFQVRMKDG-UHFFFAOYSA-M 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000001788 irregular Effects 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011859 microparticle Substances 0.000 description 2
- 229910052901 montmorillonite Inorganic materials 0.000 description 2
- 239000011253 protective coating Substances 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 241000209504 Poaceae Species 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000009418 agronomic effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 229920001222 biopolymer Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/26—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
Definitions
- the present invention is related to the field of agricultural formulations, specifically to herbicidal formulations.
- the invention also is related to granular formulations from which the crop protection active ingredient is controllably released.
- Sulfentrazone is a herbicide for the control of broadleaf weeds and some grasses in crops such as soybeans, chickpeas, tobacco, sugarcane, rice and turf.
- Sulfentrazone is absorbed by both roots and foliage, and is translocated within the plant from the point of uptake. Certain crops evidence phytotoxicity upon foliar application of sulfentrazone.
- US Patent Application Publication 2005/018952 discloses slow-release formulations useful for the preparation of seed- or particle-coated herbicidal compositions.
- the substrates to be coated can be plant seeds, or particles made of an ionic resin or other polymer, where the herbicide is covalently linked or ionically bound to the particle by strong interactions.
- the particles can be further microencapsulated, which can modulate the release of the herbicide.
- US Patent Application Publication 2007/0149409 discloses semi- stable complexes of pesticides with functionalized polymers with improved leaf retention, which can be in the form of granules or as coats for seeds and fertilizers. These again are based on ion exchangers and other mixed function substituted biopolymers that have the capacity to retain and or reversibly bind active ingredients.
- One aspect of the present invention is directed to a controlled-release particle or granule comprising a solid carrier core and at least one crop protection active ingredient-containing coating thereon.
- the form of the particle can be spherical, substantially spherical, non-spherical, or irregularly shaped.
- the carrier core of the controlled-release particle is a clay, a silica, peanut hull, a cellulosic, or other absorbent carrier material.
- the carrier core is a clay selected from the group consisting of montmorillonite clay, continental clay, kaolin clay, attapulgite clay and mixtures of two or more thereof, preferably montmorillonite clay.
- the particle is spherical or substantially spherical, and inert.
- the crop protection active ingredient coating comprises a herbicide, preferably a protoporphyrinogen IX oxidase (PPO) inhibitor.
- PPO protoporphyrinogen IX oxidase
- the PPO inhibitor is preferably selected from the group consisting of a diphenyl ether, an oxadiazole, a cyclic imide, and a pyrazole.
- the diphenyl ether is selected from the group consisting of acifluorfen, acifluorfen-sodium, aclonifen, bifenox, chlomitrofen (CNP), ethoxyfen, fluorodifen, fluoroglycofen-ethyl, fomesafen, furyloxyfen, lactofen, nitrofen, nitrofluorfen and oxyfluorfen.
- the oxadiazole is selected from the group consisting of oxadiargyl and oxadiazon.
- the cyclic imide is selected from the group consisting of azafenidin, butafenacil, cinidon-ethyl, flumiclorac-pentyl, flumioxazin, flumipropyn, flupropacil, fluthiacet-methyl, sulfentrazone, carfentrazone-ethyl and thidiazimin.
- the pyrazole is selected from the group consisting of ET-751 , JV 485 and nipyraclofen.
- the PPO inhibitor is sulfentrazone.
- the coating of active ingredient, preferably sulfentrazone is about 0.1 wt to about 5 wt based on the weight of the finished granular particle.
- the controlled-release particle further comprises a hydrophobic protectant coating, or overcoating, which is on the surface of the controlled-release particle, and on top of the active ingredient coating.
- the hydrophobic overcoating preferably comprises hydrophobic oils and/or waxes, including vegetable oils, mineral oils, synthetic oils, natural waxes, synthetic waxes, and mixtures of two or more thereof.
- the coating is selected from the group consisting of linseed oil, refined mineral oil, carnauba wax, and mixtures of two or more thereof.
- Another aspect of the present invention is directed to a controlled-release formulation
- a controlled-release formulation comprising a population of controlled-release particles or granules comprising a solid carrier core, at least one crop protection active ingredient- containing coating thereon and a hydrophobic overcoating, where the crop protection active ingredient coating comprises a herbicide.
- the form of the particles can be spherical, substantially spherical or non-spherical, or irregularly shaped.
- the particles are spherical or substantially spherical.
- the carrier core of the controlled-release particles is a clay, a silica, peanut hull, a cellulosic, or other absorbent carrier material.
- the carrier core is a clay selected from the group consisting of montmorillonite clay, continental clay, kaolin clay, attapulgite clay and mixtures of two or more thereof.
- the particles are inert.
- the controlled-release particles comprise a material selected from the group consisting of peanut hull, silica, cellulosics and clay.
- the particle material is a clay selected from the group consisting of montmorillonite clay, continental clay, kaolin clay, attapulgite clay and mixtures of two or more thereof, preferably montmorillonite clay.
- the herbicide of the active ingredient coating is a protoporphyrinogen IX oxidase (PPO) inhibitor.
- PPO protoporphyrinogen IX oxidase
- the PPO inhibitor is selected from the group consisting of a diphenyl ether, a oxadiazole, a cyclic imides, and a pyrazole.
- the diphenyl ether is selected from the group consisting of acifluorfen, acifluorfen-sodium, aclonifen, bifenox, chlomitrofen (CNP), ethoxyfen, fluorodifen, fluoroglycof en-ethyl, fomesafen, furyloxyfen, lactofen, nitrofen, nitrofluorfen and oxyfluorfen.
- the oxadiazole is selected from the group consisting of oxadiargyl and oxadiazon.
- the cyclic imide is selected from the group consisting of azafenidin, butafenacil, cinidon-ethyl, flumiclorac-pentyl, flumioxazin, flumipropyn, flupropacil, fluthiacet-methyl, sulfentrazone, carfentrazone-ethyl and thidiazimin.
- the pyrazole is selected from the group consisting of ET-751 , JV 485 and nipyraclofen.
- the PPO inhibitor is sulfentrazone.
- the coating of sulfentrazone is about 0.1 wt to about 5 wt based on the finished formulation.
- the protective coating comprises an oil selected from the group consisting of vegetable oils, mineral oils, synthetic oils, and mixtures of two or more thereof.
- the hydrophobic coating comprises at least one of linseed oil, refined mineral oil, carnauba wax, beeswax or any combinations thereof.
- Another aspect of the invention is directed to a method of reducing crop phytotoxicity to PPO inhibitors treatment, comprising: a) providing PPO inhibitor in a controlled-release formulation comprising particles comprising a carrier, a PPO inhibitor containing coating layer on the surface of said carrier, and a hydrophobic overcoating; b) applying said formulation to the area of interest; and c) reducing adherence of the particles to the crop plant.
- the crop can be selected from the group consisting of soybeans, chickpeas, tobacco, sugarcane, rice and turf.
- the invention is directed to a method of reducing crop phytotoxicity to sulfentrazone treatment, comprising: a) providing sulfentrazone in a controlled-release formulation comprising particles comprising a carrier, a sulfentrazone containing coating layer on the surface of said carrier, and a hydrophobic overcoating; b) applying said formulation to the area of interest; and c) reducing adherence of the particles to the crop plant.
- Another aspect of the invention is directed to a method of adjusting the release of sulfentrazone from a granular formulation, comprising coating a sulfentrazone- containing granular formulation with a hydrophobic oil and/or a hydrophobic wax in an amount effective to provide the desired release rate.
- the amount of the hydrophobic oil and/or wax is about 1 wt to about 10 wt based on the weight of the finished granular formulation.
- Another aspect of the invention is directed to a method of preparing a controlled-release granular formulation of sulfentrazone, comprising: a) providing a granular carrier selected from the group consisting of peanut hull, cellulosics, silica including sands, and clay; b) applying a solution of sulfentrazone in an appropriate solvent to provide sulfentrazone-coated granules; and c) overcoating said
- the sulfentrazone-coated granules with a hydrophobic oil or wax selected from the group consisting of linseed oil, refined mineral oil, natural and synthetic waxes including carnauba wax, and mixtures of two or more thereof.
- the solvent is preferably polypropylene glycol 200.
- the granular carrier is preferably montmorillonite clay.
- the granules are spherical or substantially spherical, and inert.
- Figure 1 shows a graph of sulfentrazone released in soil over time from various sulfentrazone formulations.
- the herbicidal controlled-release granular formulations of the present invention eliminate or reduce phytotoxicity on desired crops while at the same time extending release of active herbicide from the granule to improve the residual control of weeds.
- the hydrophobic ally coated granular formulations disclosed herein when appropriately applied to the foliage of a crop plant, do not significantly adhere to the foliage, but repel off the plant and fall to the soil surface.
- the slow release of the herbicidal active ingredient into the soil then provides desirable residual control of the target weeds without significant concomitant crop phytotoxicity.
- the hydrophobic overcoating on the granule controls the release of the herbicide, and can be adjusted to fine tune the release rate of the herbicide, thereby extending the weed control capacity of the formulation.
- the formulations and methods disclosed herein utilize simple hydrophobic oils and waxes as an overcoating or protective layer over the herbicide layer of the particle, in place of a granular particle based on heavily charged polymers that bind the layer of herbicide molecules.
- one aspect of the present invention is directed to a controlled-release particle or granule comprising a solid carrier core and at least one crop protection active ingredient-containing coating thereon.
- the form of the particle can be spherical, substantially spherical or non-spherical.
- the particle can also have an irregular shape or geometry.
- the particle can have a thickness or diameter ranging from about 500 microns to about 2500 microns.
- the particle is a microparticle having a D50 of about 600 microns to about 1500 microns.
- the carrier core of the controlled-release particle is a clay, a silica, peanut hull, a cellulosic, or other carrier material.
- the carrier material is absorbent.
- the carrier core is a clay selected from the group consisting of montmorillonite clay, continental clay, kaolin clay, attapulgite clay and mixtures of two or more thereof.
- the particle has a diameter ranging from about 500 microns to about 1500 microns when the solid particle has a spherical shape, with the measurement referring to the delivered product, prior to disintegration.
- the particle is inert and does not react with the active ingredient to chemically bind, either covalently or ionically, the herbicide or other active ingredient molecules.
- the crop protection active ingredient coating comprises a herbicide, preferably a protoporphyrinogen IX oxidase (PPO) inhibitor.
- PPO protoporphyrinogen IX oxidase
- the PPO inhibitor is preferably selected from the group consisting of a diphenyl ether, an oxadiazole, a cyclic imide, and a pyrazole.
- the diphenyl ether is selected from the group consisting of acifluorfen, acifluorfen-sodium, aclonifen, bifenox, chlomitrofen (CNP), ethoxyfen, fluorodifen, fluoroglycofen-ethyl, fomesafen, furyloxyfen, lactofen, nitrofen, nitrofluorfen and oxyfluorfen.
- the oxadiazole is selected from the group consisting of oxadiargyl and oxadiazon.
- the cyclic imide is selected from the group consisting of azafenidin, butafenacil, cinidon-ethyl, flumiclorac-pentyl, flumioxazin, flumipropyn, flupropacil, fluthiacet-methyl, sulfentrazone, carfentrazone-ethyl and thidiazimin.
- the pyrazole is selected from the group consisting of ET-751 , JV 485 and nipyraclofen.
- the PPO inhibitor is sulfentrazone.
- the coating of active ingredient is about 0.1 wt to about 5 wt based on the weight of the finished granular particle. In another embodiment the coating is about 0.15 wt to about 3 wt based on the finished granular particle. In a further embodiment the coating is about 0.2 wt to about 1 wt based on the finished granular particle. In one specific embodiment the sulfentrazone-containing coating is about 0.3 wt based on the finished granular particle.
- the controlled-release particle further comprises a hydrophobic protectant coating, or overcoating.
- the hydrophobic protectant coating is on the surface of the controlled-release particle, and on top of the active ingredient coating.
- Hydrophobic overcoatings preferably comprise hydrophobic oils and/or waxes, including vegetable oils, mineral oils, synthetic oils, natural waxes, synthetic waxes, and mixtures of two or more thereof.
- the hydrophobic protectant coating comprises an oil selected from the group consisting of vegetable oils, mineral oils, synthetic oils, and mixtures of two or more thereof.
- Preferred oils include linseed oil, refined mineral oil and mixtures of two or more thereof.
- Suitable refined mineral oils include ORCHEX® agricultural spray oils such as ORCHEX® 796 and ORCHEX® 692, available from Calumet Specialty Products Partners, L.P.
- the mineral oil may have a molecular weight ranging from 280-350 and a viscosity of 75 to 95 at 100 ° F, preferably 80 to 85, and more preferably at 82-83.
- the hydrophobic protectant coating comprises a wax selected from the group consisting of natural waxes, synthetic waxes and mixtures of two or more thereof.
- the wax is selected from the group consisting of carnauba wax, beeswax, synthetic waxes which are solid at temperatures below 50°C, and mixtures of two or more thereof.
- a preferred wax is carnauba wax.
- the coating is selected from the group consisting of linseed oil, refined mineral oil, carnauba wax, beeswax and mixtures of two or more thereof.
- the hydrophobic protectant coating of the controlled-release particle has a thickness ranging from about 1 micron to about 10 microns.
- Another aspect of the present invention is directed to a controlled-release formulation
- a controlled-release formulation comprising a population of controlled-release particles or granules comprising a solid carrier core, at least one crop protection active ingredient- containing coating thereon and a hydrophobic overcoating, where the crop protection active ingredient coating comprises a herbicide.
- the form of the particles can be spherical, substantially spherical or non-spherical.
- the particles can also have an irregular shape or geometry.
- the particles can have a thickness or diameter ranging from about 500 microns to about 2500 microns.
- the particles are microparticles having a D50 of about 600 microns to about 1500 microns.
- the carrier core of the controlled-release particles is a clay, a silica, peanut hull, a cellulosic, or other carrier material.
- the carrier material is absorbent.
- the carrier material is adsorbent.
- the carrier core is a clay selected from the group consisting of montmorillonite clay, continental clay, kaolin clay, attapulgite clay and mixtures of two or more thereof.
- the particles have diameters ranging from about 500 microns to about 1500 microns when the solid particles are spherical in shape.
- the particles are inert and do not react with the active ingredient to chemically bind, either covalently or ionically, the herbicide or other crop protection active ingredient molecule; however, the active ingredient can be either absorbed into or adsorbed onto the carrier.
- the controlled- release particles comprise a material selected from the group consisting of peanut hull, silica, cellulosics and clay.
- the particle material is a clay selected from the group consisting of montmorillonite clay, continental clay, kaolin clay, attapulgite clay and mixtures of two or more thereof.
- the clay is in the form of spherical or substantially spherical granules.
- the clay is montmorillonite clay.
- the herbicide of the active ingredient coating is a protoporphyrinogen IX oxidase (PPO) inhibitor.
- PPO protoporphyrinogen IX oxidase
- the PPO inhibitor is selected from the group consisting of a diphenyl ether, a oxadiazole, a cyclic imides, and a pyrazole.
- the diphenyl ether is selected from the group consisting of acifluorfen, acifluorfen-sodium, aclonifen, bifenox, chlomitrofen (CNP), ethoxyfen, fluorodifen, fluoroglycof en-ethyl, fomesafen, furyloxyfen, lactofen, nitrofen, nitrofluorfen and oxyfluorfen.
- the oxadiazole is selected from the group consisting of oxadiargyl and oxadiazon.
- the cyclic imide is selected from the group consisting of azafenidin, butafenacil, cinidon-ethyl, flumiclorac-pentyl, flumioxazin, flumipropyn, flupropacil, fluthiacet-methyl, sulfentrazone, carfentrazone-ethyl and thidiazimin.
- the pyrazole is selected from the group consisting of ET-751 , JV 485 and nipyraclofen.
- the PPO inhibitor is sulfentrazone.
- the coating of sulfentrazone is about 0.1 wt to about 5 wt based on the finished formulation, preferably about 0.15 wt to about 3 wt based on the finished formulation. In a further embodiment the coating is about 0.2 wt to about 1 wt based on the finished granular formulation. In a specific embodiment sulfentrazone is present in an amount of about 0.3 wt based on the finished formulation.
- the protective coating comprises an oil selected from the group consisting of vegetable oils, mineral oils, synthetic oils, and mixtures of two or more thereof.
- the oil is selected from the group consisting of linseed oil, refined mineral oil, other natural harvested oils, other synthetic oils, and mixtures of two or more thereof.
- the coating comprises a wax selected from the group consisting of natural waxes, synthetic waxes and mixtures of two or more thereof.
- the wax is selected from the group consisting of carnauba wax, beeswax and mixtures thereof.
- the hydrophobic coating comprises at least one of linseed oil, refined mineral oil, carnauba wax, beeswax or any combinations thereof.
- Another aspect of the invention is directed to a method of reducing crop phytotoxicity to sulfentrazone treatment, comprising: a) providing sulfentrazone in a controlled-release formulation comprising particles comprising a carrier, a sulfentrazone containing coating layer on the surface of said carrier, and a hydrophobic overcoating; b) applying said formulation to the area of interest; and c) reducing adherence of the particles to the crop plant.
- the crop is selected from the group consisting of soybeans, chickpeas, tobacco, sugarcane, rice and turf.
- Another aspect of the invention is directed to a method of adjusting the release of sulfentrazone from a granular formulation, comprising coating a sulfentrazone- containing granular formulation with a hydrophobic oil and/or a hydrophobic wax in an amount effective to provide the desired release rate.
- the amount of the hydrophobic oil and/or wax is about 1 wt to about 10 wt based on the weight of the finished granular formulation, preferably about 1.5 wt to about 5 wt based on the finished granular formulation.
- the amount of the hydrophobic oil and/or wax is about 2 wt to about 4 wt based on the finished granular formulation.
- the amount of the hydrophobic oil and/or wax is about 3 wt based on the weight of the finished granular formulation.
- Another aspect of the invention is directed to a method of preparing a controlled-release granular formulation of sulfentrazone, comprising: a) providing a granular carrier selected from the group consisting of peanut hull, cellulosics, silica and clay; b) applying a solution of sulfentrazone in an appropriate solvent to provide sulfentrazone-coated granules; and c) overcoating said sulfentrazone-coated granules with a hydrophobic oil or wax selected from the group consisting of linseed oil, refined mineral oil, carnauba wax, beeswax and mixtures of two or more thereof.
- a hydrophobic oil or wax selected from the group consisting of linseed oil, refined mineral oil, carnauba wax, beeswax and mixtures of two or more thereof.
- the solvent is polypropylene glycol 200.
- the granular carrier is montmorillonite clay.
- the clay is in the form of spherical granules.
- the granular carrier is inert.
- the granular carrier is spherical or substantially spherical in form.
- a variety of absorbent granular carriers are suitable for the presently disclosed granular formulations.
- Such granular carriers include materials selected from peanut hulls, clays, cellulosics such as paper, and other such carriers known in the formulation arts.
- Clays include montmorillonite, attapulgite, kaolin, and continental clays, as well as other clays known in the formulation arts.
- a preferred clay is montmorillonite.
- the granules are spherical or substantially spherical.
- Preferred granules include VergeTM granules and BIODAC® granules, available from Verge Granules, 410 N.
- VergeTM granules are inert dustless carrier granules made from clay.
- BIODAC® granules are inert dustless carrier granules made from cellulose/paper.
- Preparation Sulfentrazone was dissolved in polyethylene glycol 200 (PEG 200) under mild heating. Into a weighed sample of VergeTM granules under continuous mixing in a granular mixer (Hobart blender) at room temperature, the PEG 200 solution of sulfentrazone was sprayed onto the granules using a DeVilbiss compressed air driven sprayer. Mixing was continued until the solution was completely absorbed by the granules.
- PEG 200 polyethylene glycol 200
- Example 2 Sulfentrazone 0.3% Granule coated with carnauba wax
- Example 2 The method of Example 2 was used with the following modification. After the PEG 200 solution of sulfentrazone was sprayed onto the granules, warmed linseed oil (liquid at room temperature) was applied by DeVilbiss sprayer under continuous mixing. After all of the linseed oil was applied the granules were mixed until the materials were completely absorbed.
- Procedure 1 gram of each of the above Examples 1 through 4 was placed into a petri dish containing 17 mL of deionized water. The granules were visualized for time to dispersal, with data summarized in the following table.
- Procedure An in-vitro method of measuring the release of sulfentrazone in aqueous media was developed.
- a 1 -Liter container was filled to the mark with deionized water (water of any pH, salinity, mineral composition or temperature can be used).
- the water was at room temperature (approx. 20°C).
- a sample of treated granules encased in a container with one face being of 100 mesh (US) screen (equivalent to 150 micron mesh) was placed in the water.
- the water was agitated with a magnetic stirrer placed to the side of the container of granules. At various time points an aliquot of the solution was withdrawn from the beaker.
- a UV spectrum was run on the aliquot to measure the concentration of sulfentrazone.
- the UV assay was performed at a wavelength of 250 nm using a 1-cm cuvette. The aliquot was then added back to the test beaker, and the beaker was tightly covered to avoid evaporation of the solution. The change in sulfentrazone concentration over time was recorded.
- Trial 2 0.3% sulfentrazone on VergeTM Lph D140 + 3% carnauba wax coating
- SPARTAN® 4F is a flowable formulation containing four pounds of sulfentrazone per gallon, available from FMC Corporation. The formulations were applied to the top of the soil column. The columns were incubated for 1 hour and then eluted at Time 0 and seven days after treatment.
- the granules of Examples 1-4 start to release sulfentrazone immediately, but do not release their entire load when compared to the control formulations technical sulfentrazone and SPARTAN® 4F. Since the granules start to release AI (Active Ingredient) on contact with moisture, under dry agronomic conditions the dry granules would be expected to lie on the soil and not release AI until rain or irrigation occurred.
- AI Active Ingredient
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Abstract
Description
Claims
Priority Applications (8)
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UAA201700708A UA118799C2 (en) | 2014-06-27 | 2015-06-25 | Controlled-release sulfentrazone to safen plants |
MX2016017114A MX2016017114A (en) | 2014-06-27 | 2015-06-25 | Controlled-release sulfentrazone to safen plants. |
AP2016009622A AP2016009622A0 (en) | 2014-06-27 | 2015-06-25 | Controlled-release sulfentrazone to safen plants |
CA2951710A CA2951710C (en) | 2014-06-27 | 2015-06-25 | Controlled-release sulfentrazone to safen plants |
AU2015279763A AU2015279763B2 (en) | 2014-06-27 | 2015-06-25 | Controlled-release sulfentrazone to safen plants |
MYPI2016704721A MY184110A (en) | 2014-06-27 | 2015-06-25 | Controlled-release sulfentrazone to safen plants |
IL249405A IL249405B (en) | 2014-06-27 | 2016-12-06 | Controlled-release sulfentrazone to safen plants |
PH12016502434A PH12016502434A1 (en) | 2014-06-27 | 2016-12-06 | Controlled-release sulfentrazone to safen plants |
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US201462018145P | 2014-06-27 | 2014-06-27 | |
US62/018,145 | 2014-06-27 |
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AP (1) | AP2016009622A0 (en) |
AR (1) | AR100943A1 (en) |
AU (1) | AU2015279763B2 (en) |
CA (1) | CA2951710C (en) |
GT (1) | GT201600267A (en) |
IL (1) | IL249405B (en) |
MX (1) | MX2016017114A (en) |
MY (1) | MY184110A (en) |
PH (1) | PH12016502434A1 (en) |
UA (1) | UA118799C2 (en) |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN106818747A (en) * | 2016-12-15 | 2017-06-13 | 东莞市联洲知识产权运营管理有限公司 | A kind of coated slow-release plant growth regulator and preparation method and application |
US11753383B2 (en) | 2016-12-20 | 2023-09-12 | Fmc Corporation | Polymorphs of herbicidal sulfonamides |
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WO2001052650A2 (en) * | 2000-01-21 | 2001-07-26 | Ishihara Sangyo Kaisha, Ltd. | Herbicidal microemulsion |
US20060099233A1 (en) * | 2004-03-31 | 2006-05-11 | E.I.D. Parry (India) Limited | Granular formulation of neem seed extract and its process thereof |
US20070280981A1 (en) * | 2006-06-02 | 2007-12-06 | The Andersons, Inc. | Adherent biologically active ingredient carrier granule |
US20090081262A1 (en) * | 2005-08-02 | 2009-03-26 | Sol-Gel Technologies Ltd. | Metal oxide coating of water insoluble ingredients |
US20110028324A1 (en) * | 2008-01-25 | 2011-02-03 | Syngenta Crop Protection, Inc. | Herbicidal compositions |
-
2015
- 2015-06-23 UY UY0001036188A patent/UY36188A/en not_active Application Discontinuation
- 2015-06-23 AR ARP150102005A patent/AR100943A1/en active IP Right Grant
- 2015-06-25 MY MYPI2016704721A patent/MY184110A/en unknown
- 2015-06-25 AU AU2015279763A patent/AU2015279763B2/en not_active Ceased
- 2015-06-25 AP AP2016009622A patent/AP2016009622A0/en unknown
- 2015-06-25 WO PCT/US2015/037740 patent/WO2015200662A1/en active Application Filing
- 2015-06-25 UA UAA201700708A patent/UA118799C2/en unknown
- 2015-06-25 CA CA2951710A patent/CA2951710C/en active Active
- 2015-06-25 MX MX2016017114A patent/MX2016017114A/en unknown
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2016
- 2016-12-06 PH PH12016502434A patent/PH12016502434A1/en unknown
- 2016-12-06 IL IL249405A patent/IL249405B/en active IP Right Grant
- 2016-12-23 GT GT201600267A patent/GT201600267A/en unknown
Patent Citations (5)
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WO2001052650A2 (en) * | 2000-01-21 | 2001-07-26 | Ishihara Sangyo Kaisha, Ltd. | Herbicidal microemulsion |
US20060099233A1 (en) * | 2004-03-31 | 2006-05-11 | E.I.D. Parry (India) Limited | Granular formulation of neem seed extract and its process thereof |
US20090081262A1 (en) * | 2005-08-02 | 2009-03-26 | Sol-Gel Technologies Ltd. | Metal oxide coating of water insoluble ingredients |
US20070280981A1 (en) * | 2006-06-02 | 2007-12-06 | The Andersons, Inc. | Adherent biologically active ingredient carrier granule |
US20110028324A1 (en) * | 2008-01-25 | 2011-02-03 | Syngenta Crop Protection, Inc. | Herbicidal compositions |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN106818747A (en) * | 2016-12-15 | 2017-06-13 | 东莞市联洲知识产权运营管理有限公司 | A kind of coated slow-release plant growth regulator and preparation method and application |
US11753383B2 (en) | 2016-12-20 | 2023-09-12 | Fmc Corporation | Polymorphs of herbicidal sulfonamides |
Also Published As
Publication number | Publication date |
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MY184110A (en) | 2021-03-18 |
UA118799C2 (en) | 2019-03-11 |
CA2951710A1 (en) | 2015-12-30 |
AP2016009622A0 (en) | 2016-12-31 |
UY36188A (en) | 2016-09-30 |
AR100943A1 (en) | 2016-11-09 |
IL249405B (en) | 2021-03-25 |
PH12016502434A1 (en) | 2017-03-06 |
IL249405A0 (en) | 2017-02-28 |
AU2015279763B2 (en) | 2018-06-28 |
MX2016017114A (en) | 2017-05-03 |
AU2015279763A1 (en) | 2017-01-05 |
GT201600267A (en) | 2019-05-22 |
CA2951710C (en) | 2022-09-13 |
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