CA2134465A1 - Reversible agricultural gel and paste formulations - Google Patents
Reversible agricultural gel and paste formulationsInfo
- Publication number
- CA2134465A1 CA2134465A1 CA002134465A CA2134465A CA2134465A1 CA 2134465 A1 CA2134465 A1 CA 2134465A1 CA 002134465 A CA002134465 A CA 002134465A CA 2134465 A CA2134465 A CA 2134465A CA 2134465 A1 CA2134465 A1 CA 2134465A1
- Authority
- CA
- Canada
- Prior art keywords
- amino
- methyl
- alkyl
- carbonyl
- sulfonylurea
- Prior art date
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 73
- 238000009472 formulation Methods 0.000 title claims abstract description 25
- 230000002441 reversible effect Effects 0.000 title description 72
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000004615 ingredient Substances 0.000 claims abstract description 14
- 230000009974 thixotropic effect Effects 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims description 63
- 239000003795 chemical substances by application Substances 0.000 claims description 45
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 40
- 229940100389 Sulfonylurea Drugs 0.000 claims description 38
- 239000000575 pesticide Substances 0.000 claims description 37
- 229920000867 polyelectrolyte Polymers 0.000 claims description 34
- -1 C1-C4 haloallcyl Chemical group 0.000 claims description 32
- 230000000361 pesticidal effect Effects 0.000 claims description 28
- 239000003792 electrolyte Substances 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
- 239000004094 surface-active agent Substances 0.000 claims description 26
- 239000000375 suspending agent Substances 0.000 claims description 25
- 239000004009 herbicide Substances 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 230000002363 herbicidal effect Effects 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 239000012736 aqueous medium Substances 0.000 claims description 10
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- 239000005496 Chlorsulfuron Substances 0.000 claims description 8
- 125000000129 anionic group Chemical group 0.000 claims description 8
- VJYIFXVZLXQVHO-UHFFFAOYSA-N chlorsulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 VJYIFXVZLXQVHO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
- 125000002091 cationic group Chemical group 0.000 claims description 7
- 230000000087 stabilizing effect Effects 0.000 claims description 7
- 239000000417 fungicide Substances 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 6
- 239000005623 Thifensulfuron-methyl Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 claims description 5
- BNYHRGTXRPWASY-UHFFFAOYSA-N nonylsulfonylurea Chemical compound CCCCCCCCCS(=O)(=O)NC(N)=O BNYHRGTXRPWASY-UHFFFAOYSA-N 0.000 claims description 5
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 claims description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
- 239000005586 Nicosulfuron Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical compound COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- ZINJLDJMHCUBIP-UHFFFAOYSA-N ethametsulfuron-methyl Chemical compound CCOC1=NC(NC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC)=N1 ZINJLDJMHCUBIP-UHFFFAOYSA-N 0.000 claims description 3
- 230000000855 fungicidal effect Effects 0.000 claims description 3
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 3
- 239000002917 insecticide Substances 0.000 claims description 3
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 claims description 3
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000005472 Bensulfuron methyl Substances 0.000 claims description 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 2
- 239000005584 Metsulfuron-methyl Substances 0.000 claims description 2
- BGNQYGRXEXDAIQ-UHFFFAOYSA-N Pyrazosulfuron-ethyl Chemical compound C1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OCC BGNQYGRXEXDAIQ-UHFFFAOYSA-N 0.000 claims description 2
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- NSWAMPCUPHPTTC-UHFFFAOYSA-N chlorimuron-ethyl Chemical group CCOC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(Cl)=CC(OC)=N1 NSWAMPCUPHPTTC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 claims 1
- 239000005752 Copper oxychloride Substances 0.000 claims 1
- IYUQMOCUQDDTSO-UHFFFAOYSA-N [Ca].[Cu].[Cu].[Cu].[Cu] Chemical group [Ca].[Cu].[Cu].[Cu].[Cu] IYUQMOCUQDDTSO-UHFFFAOYSA-N 0.000 claims 1
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims 1
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims 1
- 125000005133 alkynyloxy group Chemical group 0.000 claims 1
- HKMOPYJWSFRURD-UHFFFAOYSA-N chloro hypochlorite;copper Chemical compound [Cu].ClOCl HKMOPYJWSFRURD-UHFFFAOYSA-N 0.000 claims 1
- DTVOKYWXACGVGO-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-6-(trifluoromethyl)pyridine-3-carboxylate Chemical compound COC(=O)C1=CC=C(C(F)(F)F)N=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 DTVOKYWXACGVGO-UHFFFAOYSA-N 0.000 claims 1
- ZTYVMAQSHCZXLF-UHFFFAOYSA-N methyl 2-[[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoylsulfamoyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 ZTYVMAQSHCZXLF-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 claims 1
- VLCQZHSMCYCDJL-UHFFFAOYSA-N tribenuron methyl Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 VLCQZHSMCYCDJL-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 40
- 241000607479 Yersinia pestis Species 0.000 abstract description 2
- 239000003090 pesticide formulation Substances 0.000 abstract 1
- 239000012530 fluid Substances 0.000 description 107
- 230000035882 stress Effects 0.000 description 37
- 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 24
- 229910052708 sodium Inorganic materials 0.000 description 24
- 239000011734 sodium Substances 0.000 description 24
- 229920003023 plastic Polymers 0.000 description 23
- 239000004033 plastic Substances 0.000 description 23
- 239000000725 suspension Substances 0.000 description 22
- 239000002253 acid Substances 0.000 description 21
- 239000006185 dispersion Substances 0.000 description 20
- 238000003756 stirring Methods 0.000 description 17
- 238000007792 addition Methods 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 16
- 239000002563 ionic surfactant Substances 0.000 description 14
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- 239000000499 gel Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000000523 sample Substances 0.000 description 8
- 230000000007 visual effect Effects 0.000 description 8
- 239000013068 control sample Substances 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 125000001246 bromo group Chemical group Br* 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 4
- 239000005562 Glyphosate Substances 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 239000006013 carbendazim Substances 0.000 description 4
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 229940097068 glyphosate Drugs 0.000 description 4
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- QYPPRTNMGCREIM-UHFFFAOYSA-N methylarsonic acid Chemical compound C[As](O)(O)=O QYPPRTNMGCREIM-UHFFFAOYSA-N 0.000 description 4
- 238000003801 milling Methods 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 238000000518 rheometry Methods 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- 229910002012 Aerosil® Inorganic materials 0.000 description 3
- 239000005802 Mancozeb Substances 0.000 description 3
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 239000000084 colloidal system Substances 0.000 description 3
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound 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 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 238000009877 rendering Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 238000001238 wet grinding Methods 0.000 description 3
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 2
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- 239000005595 Picloram Substances 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 2
- RHKZVMUBMXGOLL-UHFFFAOYSA-N cyclopentolate hydrochloride Chemical compound Cl.C1CCCC1(O)C(C(=O)OCCN(C)C)C1=CC=CC=C1 RHKZVMUBMXGOLL-UHFFFAOYSA-N 0.000 description 2
- 229940075144 cylate Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 description 2
- 229920000940 maneb Polymers 0.000 description 2
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 2
- 230000001069 nematicidal effect Effects 0.000 description 2
- 239000005645 nematicide Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 239000004584 polyacrylic acid Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000001205 polyphosphate Substances 0.000 description 2
- 235000011176 polyphosphates Nutrition 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000011164 primary particle Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- XLNZEKHULJKQBA-UHFFFAOYSA-N terbufos Chemical compound CCOP(=S)(OCC)SCSC(C)(C)C XLNZEKHULJKQBA-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- GXEKYRXVRROBEV-FBXFSONDSA-N (1r,2s,3r,4s)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid Chemical compound C1C[C@@H]2[C@@H](C(O)=O)[C@@H](C(=O)O)[C@H]1O2 GXEKYRXVRROBEV-FBXFSONDSA-N 0.000 description 1
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 description 1
- URDNHJIVMYZFRT-KGLIPLIRSA-N (2r,3r)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pentan-3-ol Chemical compound C([C@H]([C@H](O)C(C)(C)C)N1N=CN=C1)C1=CC=C(Cl)C=C1Cl URDNHJIVMYZFRT-KGLIPLIRSA-N 0.000 description 1
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- XUNYDVLIZWUPAW-UHFFFAOYSA-N (4-chlorophenyl) n-(4-methylphenyl)sulfonylcarbamate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)OC1=CC=C(Cl)C=C1 XUNYDVLIZWUPAW-UHFFFAOYSA-N 0.000 description 1
- JWUCHKBSVLQQCO-UHFFFAOYSA-N 1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(F)C=CC=1C(C=1C(=CC=CC=1)F)(O)CN1C=NC=N1 JWUCHKBSVLQQCO-UHFFFAOYSA-N 0.000 description 1
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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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
- A01N47/14—Di-thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Catching Or Destruction (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87818992A | 1992-04-28 | 1992-04-28 | |
| US07/878,189 | 1992-04-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2134465A1 true CA2134465A1 (en) | 1993-11-11 |
Family
ID=25371553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002134465A Abandoned CA2134465A1 (en) | 1992-04-28 | 1993-04-27 | Reversible agricultural gel and paste formulations |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5538936A (OSRAM) |
| EP (1) | EP0637909B1 (OSRAM) |
| JP (1) | JPH07506112A (OSRAM) |
| CN (1) | CN1077842A (OSRAM) |
| AT (1) | ATE149074T1 (OSRAM) |
| AU (1) | AU681355B2 (OSRAM) |
| BR (1) | BR9306412A (OSRAM) |
| CA (1) | CA2134465A1 (OSRAM) |
| DE (1) | DE69308294T2 (OSRAM) |
| DK (1) | DK0637909T3 (OSRAM) |
| ES (1) | ES2098749T3 (OSRAM) |
| GR (1) | GR3023199T3 (OSRAM) |
| IL (1) | IL105520A (OSRAM) |
| TW (1) | TW280760B (OSRAM) |
| WO (1) | WO1993021763A1 (OSRAM) |
| ZA (1) | ZA932994B (OSRAM) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19506095A1 (de) * | 1994-03-04 | 1995-09-21 | Bayer Agrochem Kk | Schädlingsbekämpfungsmittel in Pastenform |
| ES2172774T3 (es) * | 1996-10-25 | 2002-10-01 | Monsanto Technology Llc | Composiciones y procedimiento para el tratamiento de plantas con sustancias quimicas exogenas. |
| AU738594B2 (en) | 1996-10-25 | 2001-09-20 | Monsanto Technology Llc | Composition and method for treating plants with exogenous chemicals |
| US6074987A (en) * | 1998-05-28 | 2000-06-13 | Bayer Corporation | Inhibiting phase separation in low viscosity water-based pesticide suspensions |
| FR2796271B1 (fr) | 1999-07-15 | 2002-01-11 | Oreal | Composition sans cire structuree sous forme rigide par un polymere |
| FR2796272B1 (fr) | 1999-07-15 | 2003-09-19 | Oreal | Composition sans cire structuree sous forme rigide par un polymere |
| FR2804018B1 (fr) | 2000-01-24 | 2008-07-11 | Oreal | Composition sans transfert structuree sous forme rigide par un polymere |
| AU7971201A (en) * | 2000-07-06 | 2002-01-14 | Huntsman Int Llc | Solid-suspending systems |
| JP3930430B2 (ja) | 2000-12-12 | 2007-06-13 | ロレアル | ポリマーの混合物を含む化粧品組成物 |
| AU2001220877A1 (en) | 2000-12-12 | 2002-06-24 | L'oreal S.A. | Cosmetic composition comprising heteropolymers and a solid substance and method of using same |
| FR2817739B1 (fr) | 2000-12-12 | 2005-01-07 | Oreal | Composition cosmetique coloree transparente ou translucide |
| US20030082126A9 (en) * | 2000-12-12 | 2003-05-01 | Pinzon Carlos O. | Cosmetic compositions containing heteropolymers and oil-soluble cationic surfactants and methods of using same |
| US7276547B2 (en) | 2000-12-12 | 2007-10-02 | L'oreal S.A. | Compositions comprising heteropolymers and at least one oil-soluble polymers chosen from alkyl celluloses and alkylated guar gums |
| US6835399B2 (en) | 2000-12-12 | 2004-12-28 | L'ORéAL S.A. | Cosmetic composition comprising a polymer blend |
| AU2001225389A1 (en) | 2000-12-12 | 2002-06-24 | L'oreal S.A. | Composition comprising at least one heteropolymer and at least one inert filler and methods for use |
| WO2002047624A1 (en) | 2000-12-12 | 2002-06-20 | L'oreal Sa | Cosmetic compositions containing at least one heteropolymer and at least one gelling agent and methods of using the same |
| US7025953B2 (en) | 2001-01-17 | 2006-04-11 | L'oreal S.A. | Nail polish composition comprising a polymer |
| FR2819399B1 (fr) | 2001-01-17 | 2003-02-21 | Oreal | Composition cosmetique contenant un polymere et une huile fluoree |
| AU2002254345B2 (en) * | 2001-09-26 | 2007-07-05 | Platte Chemical Co. | Herbicide compositions comprising imidazolinone acid |
| US6716420B2 (en) | 2001-10-05 | 2004-04-06 | L′Oreal | Methods of use and of making a mascara comprising at least one coloring agent and at least one heteropolymer |
| US7008629B2 (en) | 2002-07-22 | 2006-03-07 | L'ORéAL S.A. | Compositions comprising at least one heteropolymer and fibers, and methods of using the same |
| WO2007066208A1 (en) * | 2005-12-07 | 2007-06-14 | Bitrad Trust | Pesticidal combinations |
| CA2663446C (en) | 2006-09-22 | 2015-05-26 | Huntsman Petrochemical Corporation | Pesticide formulation with streaming birefringence |
| RU2009126591A (ru) * | 2006-12-13 | 2011-01-20 | ИННОВАФОРМ ТЕКНОЛОДЖИЗ, ЭлЭлСи (US) | Пестицидные агрегаты |
| MX2010008140A (es) * | 2008-02-20 | 2010-08-18 | Syngenta Participations Ag | Formulacion herbicida. |
| DK2544532T3 (en) | 2010-03-12 | 2017-06-06 | Monsanto Technology Llc | AGRICULTURAL GEL COMPOSITIONS |
| EP3975721A1 (en) * | 2019-05-28 | 2022-04-06 | Adama Makhteshim Ltd. | Dithiocarbamate fungicide macromolecular complexes |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL301648A (OSRAM) * | 1962-12-13 | |||
| US3157486A (en) * | 1962-12-20 | 1964-11-17 | Du Pont | Pesticidal dispersion and method for preparing the same |
| US3671215A (en) * | 1970-01-02 | 1972-06-20 | Velsicol Chemical Corp | Silvicidal composition and method |
| US3930838A (en) * | 1970-09-10 | 1976-01-06 | Montecatini Edison S.P.A. | S-benzyl-n,n-disec-butylthiocarbamate and its use as a rice field herbicide and a rice growth stimulant |
| BE786491A (fr) * | 1971-07-22 | 1973-01-19 | Ici Ltd | Compositions herbicides ameliorees |
| EP0088484A1 (en) * | 1982-02-04 | 1983-09-14 | Fbc Limited | Herbicidal thiadiazolyl N-aminoureas |
| BR8401507A (pt) * | 1983-04-04 | 1984-11-13 | Du Pont | Composicao aquosa estabilizada |
| US4936900A (en) * | 1983-04-04 | 1990-06-26 | E. I. Du Pont De Nemours And Company | Stabilized aqueous formulations of sulfonylurea salts |
| US4707189A (en) * | 1984-11-07 | 1987-11-17 | Hercules Incorporated | Biostable compositions and the aqueous solutions thereof as thickeners for aqueous-based systems |
| US4800036A (en) * | 1985-05-06 | 1989-01-24 | The Dow Chemical Company | Aqueous bleach compositions thickened with a viscoelastic surfactant |
| US4808215A (en) * | 1985-10-28 | 1989-02-28 | Calgon Corporation | Method of improving the flowability of agro-chemical slurries |
| FR2600862B1 (fr) * | 1986-03-10 | 1990-04-13 | Rhone Poulenc Chim Base | Compositions aqueuses contenant un compose cationique et de la gomme xanthane et procede de preparation. |
| US4910248A (en) * | 1987-12-21 | 1990-03-20 | Exxon Research And Engineering Company | Mixtures of colloidal rod-like viscoelastic fluids and anionic-alkyl containing copolymers |
| GB8906234D0 (en) * | 1989-03-17 | 1989-05-04 | Albright & Wilson | Agrochemical suspensions |
| FR2648014B1 (fr) * | 1989-06-13 | 1993-06-11 | Rhone Poulenc Agrochimie | Association herbicide a base de bromoxynil ou de l'un de ses derives a effet synergique |
| US5078732A (en) * | 1990-04-06 | 1992-01-07 | Ceniceros Robert C | Oral hygiene device for young children |
| US5139152A (en) * | 1990-07-18 | 1992-08-18 | Rhone-Poulenc Ag Company | Water dispersible gel formulations |
-
1993
- 1993-04-16 TW TW082102926A patent/TW280760B/zh active
- 1993-04-27 US US08/325,263 patent/US5538936A/en not_active Expired - Fee Related
- 1993-04-27 AU AU51551/93A patent/AU681355B2/en not_active Ceased
- 1993-04-27 CA CA002134465A patent/CA2134465A1/en not_active Abandoned
- 1993-04-27 EP EP93912325A patent/EP0637909B1/en not_active Expired - Lifetime
- 1993-04-27 DE DE69308294T patent/DE69308294T2/de not_active Expired - Fee Related
- 1993-04-27 BR BR9306412A patent/BR9306412A/pt not_active Application Discontinuation
- 1993-04-27 WO PCT/US1993/003711 patent/WO1993021763A1/en not_active Ceased
- 1993-04-27 DK DK93912325.3T patent/DK0637909T3/da active
- 1993-04-27 ES ES93912325T patent/ES2098749T3/es not_active Expired - Lifetime
- 1993-04-27 IL IL10552093A patent/IL105520A/en not_active IP Right Cessation
- 1993-04-27 AT AT93912325T patent/ATE149074T1/de not_active IP Right Cessation
- 1993-04-27 JP JP5519344A patent/JPH07506112A/ja active Pending
- 1993-04-28 CN CN93104982A patent/CN1077842A/zh active Pending
- 1993-04-28 ZA ZA932994A patent/ZA932994B/xx unknown
-
1997
- 1997-04-21 GR GR970400860T patent/GR3023199T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69308294T2 (de) | 1997-09-04 |
| AU5155193A (en) | 1993-11-29 |
| TW280760B (OSRAM) | 1996-07-11 |
| BR9306412A (pt) | 1998-09-15 |
| US5538936A (en) | 1996-07-23 |
| AU681355B2 (en) | 1997-08-28 |
| WO1993021763A1 (en) | 1993-11-11 |
| GR3023199T3 (en) | 1997-07-30 |
| DK0637909T3 (OSRAM) | 1997-03-17 |
| ATE149074T1 (de) | 1997-03-15 |
| IL105520A0 (en) | 1993-08-18 |
| DE69308294D1 (de) | 1997-04-03 |
| JPH07506112A (ja) | 1995-07-06 |
| EP0637909B1 (en) | 1997-02-26 |
| CN1077842A (zh) | 1993-11-03 |
| IL105520A (en) | 1996-12-05 |
| ES2098749T3 (es) | 1997-05-01 |
| EP0637909A1 (en) | 1995-02-15 |
| ZA932994B (en) | 1994-10-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |