CA2160158C - Formulation solide pour la protection des cultures - Google Patents

Formulation solide pour la protection des cultures Download PDF

Info

Publication number: CA2160158C
Authority: CA; Canada
Prior art keywords: polyvinylpyrrolidone; pyrethroid insecticide; solid concentrate; pyrethroid; concentrate
Prior art date: 1993-04-08
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA002160158A

Other languages

English (en)

Other versions

CA2160158A1 (fr

Inventor

Robert Bryan Hammond

David John Wedlock

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Shell Internationale Research Maatschappij BV

Original Assignee

Shell Internationale Research Maatschappij BV

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1993-04-08

Filing date

1994-04-06

Publication date

2006-07-04

1994-04-06 Application filed by Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV

1994-04-06 Priority claimed from PCT/EP1994/001087 external-priority patent/WO1994023579A1/fr

1994-10-27 Publication of CA2160158A1 publication Critical patent/CA2160158A1/fr

2006-07-04 Application granted granted Critical

2006-07-04 Publication of CA2160158C publication Critical patent/CA2160158C/fr

2014-04-06 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000007787 solid Substances 0.000 title claims abstract description 47
239000000203 mixture Substances 0.000 title description 52
238000009472 formulation Methods 0.000 title description 41
239000001267 polyvinylpyrrolidone Substances 0.000 claims abstract description 52
229920000036 polyvinylpyrrolidone Polymers 0.000 claims abstract description 52
235000013855 polyvinylpyrrolidone Nutrition 0.000 claims abstract description 52
239000002728 pyrethroid Substances 0.000 claims abstract description 48
239000012141 concentrate Substances 0.000 claims abstract description 46
238000000034 method Methods 0.000 claims abstract description 38
239000002917 insecticide Substances 0.000 claims abstract description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 28
239000006185 dispersion Substances 0.000 claims abstract description 13
241001124076 Aphididae Species 0.000 claims abstract description 11
241000607479 Yersinia pestis Species 0.000 claims abstract description 11
KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical group CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 claims description 34
239000002904 solvent Substances 0.000 claims description 24
125000005843 halogen group Chemical group 0.000 claims description 15
239000005877 Alpha-Cypermethrin Substances 0.000 claims description 12
OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
239000005892 Deltamethrin Substances 0.000 claims description 8
229960002483 decamethrin Drugs 0.000 claims description 8
238000003801 milling Methods 0.000 claims description 8
239000000243 solution Substances 0.000 claims description 8
NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 claims description 7
238000001816 cooling Methods 0.000 claims description 6
239000005895 Esfenvalerate Substances 0.000 claims description 5
229960001591 cyfluthrin Drugs 0.000 claims description 5
QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 claims description 5
NYPJDWWKZLNGGM-RPWUZVMVSA-N esfenvalerate Chemical compound C=1C([C@@H](C#N)OC(=O)[C@@H](C(C)C)C=2C=CC(Cl)=CC=2)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-RPWUZVMVSA-N 0.000 claims description 5
-1 methylenedioxy groups Chemical group 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
238000001125 extrusion Methods 0.000 description 24
239000004480 active ingredient Substances 0.000 description 10
230000000052 comparative effect Effects 0.000 description 10
239000004546 suspension concentrate Substances 0.000 description 10
239000004615 ingredient Substances 0.000 description 8
241000253994 Acyrthosiphon pisum Species 0.000 description 6
125000001309 chloro group Chemical group Cl* 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000000839 emulsion Substances 0.000 description 6
239000000463 material Substances 0.000 description 6
239000002245 particle Substances 0.000 description 6
229920000642 polymer Polymers 0.000 description 6
239000003826 tablet Substances 0.000 description 6
230000002824 aphicidal effect Effects 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
239000008187 granular material Substances 0.000 description 5
238000012545 processing Methods 0.000 description 5
239000004094 surface-active agent Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
241000219843 Pisum Species 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000000155 melt Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
238000012360 testing method Methods 0.000 description 4
LQIAZOCLNBBZQK-UHFFFAOYSA-N 1-(1,2-Diphosphanylethyl)pyrrolidin-2-one Chemical compound PCC(P)N1CCCC1=O LQIAZOCLNBBZQK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
239000000945 filler Substances 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
239000012669 liquid formulation Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000007921 spray Substances 0.000 description 3
238000011282 treatment Methods 0.000 description 3
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
231100000111 LD50 Toxicity 0.000 description 2
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
230000000895 acaricidal effect Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
229910000323 aluminium silicate Inorganic materials 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
159000000007 calcium salts Chemical class 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
239000013065 commercial product Substances 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
230000004927 fusion Effects 0.000 description 2
230000009477 glass transition Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000178 monomer Substances 0.000 description 2
RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 2
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 2
239000001120 potassium sulphate Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
238000010008 shearing Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000006104 solid solution Substances 0.000 description 2
238000000935 solvent evaporation Methods 0.000 description 2
241000894007 species Species 0.000 description 2
239000008399 tap water Substances 0.000 description 2
235000020679 tap water Nutrition 0.000 description 2
239000004557 technical material Substances 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
ZXQYGBMAQZUVMI-RDDWSQKMSA-N (1S)-cis-(alphaR)-cyhalothrin Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-RDDWSQKMSA-N 0.000 description 1
SFHVXKNMCGSLAR-UHFFFAOYSA-N 2,2,3,3-tetramethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C(O)=O)C1(C)C SFHVXKNMCGSLAR-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
OBDJZIMVJOCSIR-UHFFFAOYSA-N 2-benzyl-2-(4-chlorophenyl)-3-methyl-3-phenoxybutanoic acid Chemical compound CC(C)(C(CC1=CC=CC=C1)(C2=CC=C(C=C2)Cl)C(=O)O)OC3=CC=CC=C3 OBDJZIMVJOCSIR-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
239000005946 Cypermethrin Substances 0.000 description 1
101000749842 Homo sapiens Leukocyte cell-derived chemotaxin 1 Proteins 0.000 description 1
101001108356 Homo sapiens Nardilysin Proteins 0.000 description 1
102100040448 Leukocyte cell-derived chemotaxin 1 Human genes 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
102100021850 Nardilysin Human genes 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical class CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000001348 alkyl chlorides Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
239000001166 ammonium sulphate Substances 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000001175 calcium sulphate Substances 0.000 description 1
235000011132 calcium sulphate Nutrition 0.000 description 1
YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical class [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000012656 cationic ring opening polymerization Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229960001701 chloroform Drugs 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
QQODLKZGRKWIFG-UHFFFAOYSA-N cyfluthrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-UHFFFAOYSA-N 0.000 description 1
ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 description 1
KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 1
229960005424 cypermethrin Drugs 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000000113 differential scanning calorimetry Methods 0.000 description 1
YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000000428 dust Substances 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
XQUXKZZNEFRCAW-UHFFFAOYSA-N fenpropathrin Chemical compound CC1(C)C(C)(C)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 XQUXKZZNEFRCAW-UHFFFAOYSA-N 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000000227 grinding Methods 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
231100000092 inhalation hazard Toxicity 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
UGWALRUNBSBTGI-ZKMZRDRYSA-N kadethrin Chemical compound C(/[C@@H]1C([C@@H]1C(=O)OCC=1C=C(CC=2C=CC=CC=2)OC=1)(C)C)=C1/CCSC1=O UGWALRUNBSBTGI-ZKMZRDRYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000004898 kneading Methods 0.000 description 1
239000005910 lambda-Cyhalothrin Substances 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
235000012243 magnesium silicates Nutrition 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
229960000490 permethrin Drugs 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
238000010094 polymer processing Methods 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000012254 powdered material Substances 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
239000002426 superphosphate Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
239000004562 water dispersible granule Substances 0.000 description 1
229920003169 water-soluble polymer Polymers 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1

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Agricultural Chemicals And Associated Chemicals (AREA)

CA002160158A 1993-04-08 1994-04-06 Formulation solide pour la protection des cultures Expired - Fee Related CA2160158C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
EP93302792.2		1993-04-08
EP93302792		1993-04-08
PCT/EP1994/001087 WO1994023579A1 (fr)	1993-04-08	1994-04-06	Formulation solide pour la protection des cultures

Publications (2)

Publication Number	Publication Date
CA2160158A1 CA2160158A1 (fr)	1994-10-27
CA2160158C true CA2160158C (fr)	2006-07-04

Family

ID=36648489

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002160158A Expired - Fee Related CA2160158C (fr)	1993-04-08	1994-04-06	Formulation solide pour la protection des cultures

Country Status (1)

Country	Link
CA (1)	CA2160158C (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2020245235A1 (fr) *	2019-06-05	2020-12-10	Bayer Aktiengesellschaft	Formulations stabilisées de produits phytosanitaires

1994
- 1994-04-06 CA CA002160158A patent/CA2160158C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2160158A1 (fr)	1994-10-27

Legal Events

Date	Code	Title	Description
2001-03-14	EEER	Examination request
2012-04-10	MKLA	Lapsed

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