CA2757055C - Solid forms of an azocyclic amide and fungicidal compositions comprising the same - Google Patents
Solid forms of an azocyclic amide and fungicidal compositions comprising the same Download PDFInfo
- Publication number
- CA2757055C CA2757055C CA2757055A CA2757055A CA2757055C CA 2757055 C CA2757055 C CA 2757055C CA 2757055 A CA2757055 A CA 2757055A CA 2757055 A CA2757055 A CA 2757055A CA 2757055 C CA2757055 C CA 2757055C
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- Prior art keywords
- compound
- water
- polymorph
- fungicides
- polymorph form
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- 239000000203 mixture Substances 0.000 title claims abstract description 397
- 239000007787 solid Substances 0.000 title claims abstract description 176
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 115
- 150000001408 amides Chemical class 0.000 title description 7
- 239000000417 fungicide Substances 0.000 claims abstract description 229
- 239000007788 liquid Substances 0.000 claims abstract description 157
- 238000000034 method Methods 0.000 claims abstract description 122
- 239000004094 surface-active agent Substances 0.000 claims abstract description 67
- 201000010099 disease Diseases 0.000 claims abstract description 51
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 51
- 239000000969 carrier Substances 0.000 claims abstract description 23
- 239000003085 diluting agent Substances 0.000 claims abstract description 22
- 239000002917 insecticide Substances 0.000 claims abstract description 13
- 244000000004 fungal plant pathogen Species 0.000 claims abstract description 8
- IAQLCKZJGNTRDO-UHFFFAOYSA-N 1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2CC(ON=2)C=2C(=CC=CC=2F)F)CC1 IAQLCKZJGNTRDO-UHFFFAOYSA-N 0.000 claims abstract 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 136
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 93
- 239000002904 solvent Substances 0.000 claims description 85
- 239000013078 crystal Substances 0.000 claims description 64
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 60
- BREATYVWRHIPIY-UHFFFAOYSA-N amisulbrom Chemical compound CN(C)S(=O)(=O)N1C=NC(S(=O)(=O)N2C3=CC(F)=CC=C3C(Br)=C2C)=N1 BREATYVWRHIPIY-UHFFFAOYSA-N 0.000 claims description 58
- 239000005727 Amisulbrom Substances 0.000 claims description 55
- GGKQIOFASHYUJZ-UHFFFAOYSA-N ametoctradin Chemical compound NC1=C(CCCCCCCC)C(CC)=NC2=NC=NN21 GGKQIOFASHYUJZ-UHFFFAOYSA-N 0.000 claims description 55
- 239000005726 Ametoctradin Substances 0.000 claims description 54
- 239000002002 slurry Substances 0.000 claims description 52
- 239000011541 reaction mixture Substances 0.000 claims description 49
- 239000007791 liquid phase Substances 0.000 claims description 33
- 238000002156 mixing Methods 0.000 claims description 31
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 11
- WYEMLYFITZORAB-UHFFFAOYSA-N boscalid Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC=C1NC(=O)C1=CC=CN=C1Cl WYEMLYFITZORAB-UHFFFAOYSA-N 0.000 claims description 7
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 claims description 7
- 239000005740 Boscalid Substances 0.000 claims description 6
- 239000005807 Metalaxyl Substances 0.000 claims description 6
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 claims description 6
- XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 claims description 5
- QNBTYORWCCMPQP-JXAWBTAJSA-N (Z)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/C(=O)N1CCOCC1 QNBTYORWCCMPQP-JXAWBTAJSA-N 0.000 claims description 5
- PCCSBWNGDMYFCW-UHFFFAOYSA-N 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(C)(C=2C=CC(OC=3C=CC=CC=3)=CC=2)OC(=O)N1NC1=CC=CC=C1 PCCSBWNGDMYFCW-UHFFFAOYSA-N 0.000 claims description 5
- 239000005736 Benthiavalicarb Substances 0.000 claims description 5
- 239000005754 Cyazofamid Substances 0.000 claims description 5
- 239000005756 Cymoxanil Substances 0.000 claims description 5
- 239000005761 Dimethomorph Substances 0.000 claims description 5
- 239000005772 Famoxadone Substances 0.000 claims description 5
- 239000005789 Folpet Substances 0.000 claims description 5
- 239000005802 Mancozeb Substances 0.000 claims description 5
- 239000005860 Valifenalate Substances 0.000 claims description 5
- VVSLYIKSEBPRSN-PELKAZGASA-N benthiavalicarb Chemical compound C1=C(F)C=C2SC([C@@H](C)NC(=O)[C@@H](NC(O)=O)C(C)C)=NC2=C1 VVSLYIKSEBPRSN-PELKAZGASA-N 0.000 claims description 5
- YXKMMRDKEKCERS-UHFFFAOYSA-N cyazofamid Chemical compound CN(C)S(=O)(=O)N1C(C#N)=NC(Cl)=C1C1=CC=C(C)C=C1 YXKMMRDKEKCERS-UHFFFAOYSA-N 0.000 claims description 5
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 claims description 5
- 230000003472 neutralizing effect Effects 0.000 claims description 5
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 claims description 5
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 claims description 4
- LQDARGUHUSPFNL-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COC(F)(F)C(F)F)CN1C=NC=N1 LQDARGUHUSPFNL-UHFFFAOYSA-N 0.000 claims description 4
- PFFIDZXUXFLSSR-UHFFFAOYSA-N 1-methyl-N-[2-(4-methylpentan-2-yl)-3-thienyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound S1C=CC(NC(=O)C=2C(=NN(C)C=2)C(F)(F)F)=C1C(C)CC(C)C PFFIDZXUXFLSSR-UHFFFAOYSA-N 0.000 claims description 4
- HZJKXKUJVSEEFU-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile Chemical compound C=1C=C(Cl)C=CC=1C(CCCC)(C#N)CN1C=NC=N1 HZJKXKUJVSEEFU-UHFFFAOYSA-N 0.000 claims description 4
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 claims description 4
- KWLVWJPJKJMCSH-UHFFFAOYSA-N 2-(4-chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-yn-1-yloxy)acetamide Chemical compound C1=C(OCC#C)C(OC)=CC(CCNC(=O)C(OCC#C)C=2C=CC(Cl)=CC=2)=C1 KWLVWJPJKJMCSH-UHFFFAOYSA-N 0.000 claims description 4
- 239000005730 Azoxystrobin Substances 0.000 claims description 4
- 239000005739 Bordeaux mixture Substances 0.000 claims description 4
- 239000005746 Carboxin Substances 0.000 claims description 4
- 239000005747 Chlorothalonil Substances 0.000 claims description 4
- 239000005752 Copper oxychloride Substances 0.000 claims description 4
- 239000005757 Cyproconazole Substances 0.000 claims description 4
- 239000005760 Difenoconazole Substances 0.000 claims description 4
- 239000005780 Fluazinam Substances 0.000 claims description 4
- 239000005781 Fludioxonil Substances 0.000 claims description 4
- 239000005782 Fluopicolide Substances 0.000 claims description 4
- 239000005797 Iprovalicarb Substances 0.000 claims description 4
- 239000005800 Kresoxim-methyl Substances 0.000 claims description 4
- NWUWYYSKZYIQAE-ZBFHGGJFSA-N L-(R)-iprovalicarb Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)N[C@H](C)C1=CC=C(C)C=C1 NWUWYYSKZYIQAE-ZBFHGGJFSA-N 0.000 claims description 4
- 239000005804 Mandipropamid Substances 0.000 claims description 4
- 239000005811 Myclobutanil Substances 0.000 claims description 4
- 239000005816 Penthiopyrad Substances 0.000 claims description 4
- 239000005818 Picoxystrobin Substances 0.000 claims description 4
- 239000005822 Propiconazole Substances 0.000 claims description 4
- 239000005824 Proquinazid Substances 0.000 claims description 4
- 239000005869 Pyraclostrobin Substances 0.000 claims description 4
- 239000005831 Quinoxyfen Substances 0.000 claims description 4
- 239000005837 Spiroxamine Substances 0.000 claims description 4
- 239000005839 Tebuconazole Substances 0.000 claims description 4
- 239000005840 Tetraconazole Substances 0.000 claims description 4
- 239000005857 Trifloxystrobin Substances 0.000 claims description 4
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 claims description 4
- USRKFGIXLGKMKU-ABAIWWIYSA-N benthiavalicarb-isopropyl Chemical compound C1=C(F)C=C2SC([C@@H](C)NC(=O)[C@H](C(C)C)NC(=O)OC(C)C)=NC2=C1 USRKFGIXLGKMKU-ABAIWWIYSA-N 0.000 claims description 4
- OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 claims description 4
- 229940118790 boscalid Drugs 0.000 claims description 4
- GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 claims description 4
- HKMOPYJWSFRURD-UHFFFAOYSA-N chloro hypochlorite;copper Chemical compound [Cu].ClOCl HKMOPYJWSFRURD-UHFFFAOYSA-N 0.000 claims description 4
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 claims description 4
- 229910000365 copper sulfate Inorganic materials 0.000 claims description 4
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 4
- BQYJATMQXGBDHF-UHFFFAOYSA-N difenoconazole Chemical compound O1C(C)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 BQYJATMQXGBDHF-UHFFFAOYSA-N 0.000 claims description 4
- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 claims description 4
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 claims description 4
- GBOYJIHYACSLGN-UHFFFAOYSA-N fluopicolide Chemical compound ClC1=CC(C(F)(F)F)=CN=C1CNC(=O)C1=C(Cl)C=CC=C1Cl GBOYJIHYACSLGN-UHFFFAOYSA-N 0.000 claims description 4
- FQKUGOMFVDPBIZ-UHFFFAOYSA-N flusilazole Chemical compound C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 FQKUGOMFVDPBIZ-UHFFFAOYSA-N 0.000 claims description 4
- ZOTBXTZVPHCKPN-HTXNQAPBSA-N kresoxim-methyl Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC=C1C ZOTBXTZVPHCKPN-HTXNQAPBSA-N 0.000 claims description 4
- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 claims description 4
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 claims description 4
- FLVBXVXXXMLMOX-UHFFFAOYSA-N proquinazid Chemical compound C1=C(I)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1 FLVBXVXXXMLMOX-UHFFFAOYSA-N 0.000 claims description 4
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 claims description 4
- WRPIRSINYZBGPK-UHFFFAOYSA-N quinoxyfen Chemical compound C1=CC(F)=CC=C1OC1=CC=NC2=CC(Cl)=CC(Cl)=C12 WRPIRSINYZBGPK-UHFFFAOYSA-N 0.000 claims description 4
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 claims description 4
- SOUGWDPPRBKJEX-UHFFFAOYSA-N 3,5-dichloro-N-(1-chloro-3-methyl-2-oxopentan-3-yl)-4-methylbenzamide Chemical compound ClCC(=O)C(C)(CC)NC(=O)C1=CC(Cl)=C(C)C(Cl)=C1 SOUGWDPPRBKJEX-UHFFFAOYSA-N 0.000 claims description 3
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 claims description 3
- 239000005750 Copper hydroxide Substances 0.000 claims description 3
- 239000005821 Propamocarb Substances 0.000 claims description 3
- 239000005863 Zoxamide Substances 0.000 claims description 3
- 229910001956 copper hydroxide Inorganic materials 0.000 claims description 3
- JHIPUJPTQJYEQK-ZLHHXESBSA-N orysastrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1CO\N=C(/C)\C(=N\OC)\C(\C)=N\OC JHIPUJPTQJYEQK-ZLHHXESBSA-N 0.000 claims description 3
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 claims description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 2
- MKIMSXGUTQTKJU-UHFFFAOYSA-N Propamocarb hydrochloride Chemical compound [Cl-].CCCOC(=O)NCCC[NH+](C)C MKIMSXGUTQTKJU-UHFFFAOYSA-N 0.000 claims description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 2
- BMWKXOOJBWCONP-UHFFFAOYSA-N 1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidine-4-carbothioamide Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C(N)=S)CC1 BMWKXOOJBWCONP-UHFFFAOYSA-N 0.000 claims 1
- PGONUFQCBRMACB-UHFFFAOYSA-N 2-bromo-1-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]ethanone Chemical compound FC1=CC=CC(F)=C1C1ON=C(C(=O)CBr)C1 PGONUFQCBRMACB-UHFFFAOYSA-N 0.000 claims 1
- 229940125904 compound 1 Drugs 0.000 abstract description 180
- 238000006243 chemical reaction Methods 0.000 abstract description 47
- 238000002360 preparation method Methods 0.000 abstract description 30
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 abstract description 21
- -1 alkali metal salt Chemical class 0.000 description 91
- 238000009472 formulation Methods 0.000 description 84
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 71
- 238000012360 testing method Methods 0.000 description 71
- 230000009471 action Effects 0.000 description 67
- 235000014113 dietary fatty acids Nutrition 0.000 description 66
- 239000000194 fatty acid Substances 0.000 description 66
- 229930195729 fatty acid Natural products 0.000 description 66
- 241000196324 Embryophyta Species 0.000 description 54
- 239000004480 active ingredient Substances 0.000 description 52
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- 150000004665 fatty acids Chemical class 0.000 description 34
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 32
- 241000233866 Fungi Species 0.000 description 30
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- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 24
- 229920001223 polyethylene glycol Polymers 0.000 description 23
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- 235000008504 concentrate Nutrition 0.000 description 22
- 239000012141 concentrate Substances 0.000 description 22
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 22
- 239000007921 spray Substances 0.000 description 22
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- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 20
- 229920006395 saturated elastomer Polymers 0.000 description 19
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- 238000000113 differential scanning calorimetry Methods 0.000 description 17
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 16
- 239000002671 adjuvant Substances 0.000 description 16
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 150000001298 alcohols Chemical class 0.000 description 15
- 239000012298 atmosphere Substances 0.000 description 15
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- 238000002474 experimental method Methods 0.000 description 15
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- 210000004027 cell Anatomy 0.000 description 14
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- 150000003626 triacylglycerols Chemical class 0.000 description 14
- 108010052164 Sodium Channels Proteins 0.000 description 13
- 102000018674 Sodium Channels Human genes 0.000 description 13
- 238000012512 characterization method Methods 0.000 description 13
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- 239000002736 nonionic surfactant Substances 0.000 description 12
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 12
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 11
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 11
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 11
- 240000003768 Solanum lycopersicum Species 0.000 description 11
- 244000061456 Solanum tuberosum Species 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 11
- 235000012216 bentonite Nutrition 0.000 description 11
- 230000003115 biocidal effect Effects 0.000 description 11
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- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- 235000008070 tepary bean Nutrition 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
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- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- ZDRNMODJXFOYMN-UHFFFAOYSA-N tridecyl acetate Chemical compound CCCCCCCCCCCCCOC(C)=O ZDRNMODJXFOYMN-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- MCVUKOYZUCWLQQ-UHFFFAOYSA-N tridecylbenzene Chemical class CCCCCCCCCCCCCC1=CC=CC=C1 MCVUKOYZUCWLQQ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ZQTYRTSKQFQYPQ-UHFFFAOYSA-N trisiloxane Chemical class [SiH3]O[SiH2]O[SiH3] ZQTYRTSKQFQYPQ-UHFFFAOYSA-N 0.000 description 1
- 108010013280 ubiquinol oxidase Proteins 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
- 229940045145 uridine Drugs 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- 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
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
-
- 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
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
- A01N59/16—Heavy metals; Compounds thereof
- A01N59/20—Copper
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Inorganic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17157309P | 2009-04-22 | 2009-04-22 | |
| US61/171,573 | 2009-04-22 | ||
| US31151210P | 2010-03-08 | 2010-03-08 | |
| US61/311,512 | 2010-03-08 | ||
| PCT/US2010/031546 WO2010123791A1 (en) | 2009-04-22 | 2010-04-19 | Solid forms of an azocyclic amide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2757055A1 CA2757055A1 (en) | 2010-10-28 |
| CA2757055C true CA2757055C (en) | 2017-01-17 |
Family
ID=42262664
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2757055A Active CA2757055C (en) | 2009-04-22 | 2010-04-19 | Solid forms of an azocyclic amide and fungicidal compositions comprising the same |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US8669277B2 (enExample) |
| EP (1) | EP2421861B1 (enExample) |
| JP (2) | JP6130667B2 (enExample) |
| KR (1) | KR101743309B1 (enExample) |
| CN (1) | CN102459256B (enExample) |
| AR (1) | AR076384A1 (enExample) |
| AU (1) | AU2010239456B2 (enExample) |
| CA (1) | CA2757055C (enExample) |
| CL (1) | CL2011002603A1 (enExample) |
| CO (1) | CO6400143A2 (enExample) |
| DK (1) | DK2421861T3 (enExample) |
| ES (1) | ES2402113T3 (enExample) |
| IL (1) | IL215206A (enExample) |
| MX (1) | MX2011011092A (enExample) |
| MY (1) | MY152264A (enExample) |
| NZ (1) | NZ595278A (enExample) |
| PE (2) | PE20120879A1 (enExample) |
| PL (1) | PL2421861T3 (enExample) |
| PT (1) | PT2421861E (enExample) |
| RU (1) | RU2528975C2 (enExample) |
| TW (1) | TWI508962B (enExample) |
| UY (1) | UY32567A (enExample) |
| WO (1) | WO2010123791A1 (enExample) |
| ZA (1) | ZA201106981B (enExample) |
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| ES2553620T3 (es) | 2009-12-21 | 2015-12-10 | Bayer Cropscience Ag | Bis(difluorometil)pirazoles como fungicidas |
| EP2588456A1 (en) | 2010-07-02 | 2013-05-08 | Syngenta Participations AG | Novel microbiocidal dioxime ether derivatives |
| WO2012010568A1 (en) | 2010-07-19 | 2012-01-26 | Syngenta Participations Ag | Microbicides |
| CN103003268A (zh) | 2010-07-19 | 2013-03-27 | 先正达参股股份有限公司 | 作为杀微生物剂的异噁唑、异噻唑、呋喃以及噻吩化合物 |
| CA2804355A1 (en) | 2010-07-29 | 2012-02-02 | Syngenta Participations Ag | Novel microbiocidal dioxime ether derivatives |
| CN103124723A (zh) | 2010-09-23 | 2013-05-29 | 先正达参股股份有限公司 | 新颖的杀微生物剂 |
| AR083112A1 (es) | 2010-10-01 | 2013-01-30 | Syngenta Participations Ag | Metodo para controlar enfermedades fitopatogenas y composiciones fungicidas utiles para dicho control |
| EP2624699B1 (en) * | 2010-10-07 | 2018-11-21 | Bayer CropScience Aktiengesellschaft | Fungicide composition comprising a tetrazolyloxime derivative and a thiazolylpiperidine derivative |
| CN103180307A (zh) | 2010-10-28 | 2013-06-26 | 先正达参股股份有限公司 | 新颖的杀微生物剂 |
| WO2012062844A1 (en) | 2010-11-12 | 2012-05-18 | Syngenta Participations Ag | Novel microbiocides |
| WO2012066122A1 (en) | 2010-11-18 | 2012-05-24 | Syngenta Participations Ag | 2 - (pyridin- 2 -yl) -quinazoline derivatives and their use as microbicides |
| EP2643302A1 (en) | 2010-11-23 | 2013-10-02 | Syngenta Participations AG | Insecticidal compounds |
| WO2012069601A1 (en) | 2010-11-25 | 2012-05-31 | Syngenta Participations Ag | Substituted quinazolines as fungicides |
| WO2012080376A1 (en) | 2010-12-17 | 2012-06-21 | Syngenta Participations Ag | Insecticidal compounds |
| EA201300894A1 (ru) | 2011-02-09 | 2014-01-30 | Зингента Партисипейшнс Аг | Инсектицидные соединения |
| WO2012117021A2 (en) | 2011-03-03 | 2012-09-07 | Syngenta Participations Ag | Novel microbiocidal oxime ethers |
| BR112013023798A2 (pt) | 2011-03-22 | 2016-09-20 | Syngenta Participations Ag | compostos inseticidas |
| WO2012143395A1 (en) | 2011-04-20 | 2012-10-26 | Syngenta Participations Ag | 4,5-dihydro-isoxazole derivatives as fungicides |
| WO2012175474A1 (en) | 2011-06-20 | 2012-12-27 | Syngenta Participations Ag | 1,2,3 triazole pesticides |
| EP2540718A1 (en) | 2011-06-29 | 2013-01-02 | Syngenta Participations AG. | Novel insecticides |
| WO2013007550A1 (en) | 2011-07-08 | 2013-01-17 | Syngenta Participations Ag | Fungicide mixtures |
| WO2013011010A1 (en) | 2011-07-19 | 2013-01-24 | Syngenta Participations Ag | Fungizide mixtures |
| WO2013026900A1 (en) | 2011-08-23 | 2013-02-28 | Syngenta Participations Ag | Pyridine derivatives as microbiocides |
| AR087609A1 (es) | 2011-08-23 | 2014-04-03 | Syngenta Participations Ag | Microbiocidas |
| HK1198385A1 (en) * | 2011-09-15 | 2015-04-17 | Bayer Intellectual Property Gmbh | Piperidine pyrazoles as fungicides |
| MX2014003994A (es) | 2011-10-03 | 2014-05-07 | Syngenta Participations Ag | Derivados insecticidas de 2-metoxobenzamida. |
| TWI577286B (zh) * | 2011-10-13 | 2017-04-11 | 杜邦股份有限公司 | 殺線蟲磺醯胺之固體形態 |
| BR112014010707A2 (pt) | 2011-11-04 | 2017-04-25 | Syngenta Participations Ag | compostos pesticidas |
| EP2773622A1 (en) | 2011-11-04 | 2014-09-10 | Syngenta Participations AG | Pesticidal compounds |
| EP2773617B1 (en) | 2011-11-04 | 2018-08-22 | Syngenta Participations AG | Pesticidal compounds |
| AU2012331256A1 (en) | 2011-11-04 | 2014-05-22 | Syngenta Participations Ag | Pesticidal compounds |
| WO2013092460A1 (en) | 2011-12-20 | 2013-06-27 | Syngenta Participations Ag | Cyclic bisoxime microbicides |
| TWI568721B (zh) * | 2012-02-01 | 2017-02-01 | 杜邦股份有限公司 | 殺真菌之吡唑混合物 |
| BR112014019622B8 (pt) | 2012-02-14 | 2020-05-26 | Syngenta Participations Ag | composto, seus usos, composição pesticida, material de propagação de plantas tratado e composições farmacêuticas |
| EP2641901A1 (en) | 2012-03-22 | 2013-09-25 | Syngenta Participations AG. | Novel microbiocides |
| EP2644595A1 (en) | 2012-03-26 | 2013-10-02 | Syngenta Participations AG. | N-Cyclylamides as nematicides |
| KR102140620B1 (ko) | 2012-08-30 | 2020-08-03 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 3,5-비스(할로알킬)-피라졸-4-카복실산 유도체의 탈카복실화 방법 |
| CN104755457A (zh) | 2012-10-31 | 2015-07-01 | 先正达参股股份有限公司 | 杀虫化合物 |
| BR112015014753B8 (pt) | 2012-12-20 | 2020-03-03 | Basf Agro Bv | composições, uso de uma composição, método para o combate de fungos fitopatogênicos e uso dos componentes |
| WO2014108286A1 (en) | 2013-01-09 | 2014-07-17 | Basf Se | Process for the preparation of substituted oxiranes and triazoles |
| BR112015018547A2 (pt) | 2013-02-04 | 2017-07-18 | Syngenta Participations Ag | microbiocidas |
| WO2014131572A1 (en) | 2013-02-27 | 2014-09-04 | Syngenta Participations Ag | Novel carboxamide compounds |
| JP6488278B2 (ja) | 2013-04-02 | 2019-03-20 | シンジェンタ パーティシペーションズ アーゲー | 殺虫性化合物 |
| BR112015025203B1 (pt) | 2013-04-02 | 2020-11-24 | Syngenta Participations Ag | compostos, processo para a produção de compostos, método de uso de compostos, métodos para controle de insetos, ácaros, nematódeos ou moluscos e para a proteção de plantas úteis e composição |
| WO2014167133A1 (en) | 2013-04-12 | 2014-10-16 | Syngenta Participations Ag | Fungicides comprising boron |
| WO2014173880A1 (en) | 2013-04-22 | 2014-10-30 | Syngenta Participations Ag | Novel microbiocides |
| MY183895A (en) | 2013-07-08 | 2021-03-17 | Syngenta Participations Ag | 4-membered ring carboxamides used as nematicides |
| US10512267B2 (en) | 2013-07-08 | 2019-12-24 | BASF Agro, B.V. | Compositions comprising a triazole compound and a biopesticide |
| WO2015004091A1 (en) | 2013-07-12 | 2015-01-15 | Syngenta Participations Ag | Nicotinamide derivatives and their use against nematodes |
| WO2015003991A1 (en) | 2013-07-12 | 2015-01-15 | Syngenta Participations Ag | Novel microbiocides |
| US9693551B2 (en) * | 2013-07-12 | 2017-07-04 | Valent U.S.A. Corporation | Pesticidal dispersible concentrate formulations |
| CN104336048A (zh) * | 2013-08-08 | 2015-02-11 | 陕西美邦农药有限公司 | 一种含氟噻唑吡乙酮与三唑类的杀菌组合物 |
| CN104336027B (zh) * | 2013-08-09 | 2018-07-10 | 陕西美邦农药有限公司 | 一种含氟噻唑吡乙酮的农药组合物 |
| WO2015036379A1 (en) * | 2013-09-13 | 2015-03-19 | Bayer Cropscience Ag | Fungicidal compositions containing thiazolylisoxazoline fungicide and biological fungicide |
| WO2015040141A1 (en) | 2013-09-23 | 2015-03-26 | Syngenta Participations Ag | Cyclobutylcarboxamides as nematicides |
| EA038104B1 (ru) | 2013-10-03 | 2021-07-07 | Зингента Партисипейшнс Аг | Фунгицидные композиции |
| US9783534B2 (en) * | 2013-10-17 | 2017-10-10 | Bayer Cropscience Aktiengesellschaft | Crystalline form of 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1, 3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulphonate |
| WO2015055764A1 (en) | 2013-10-18 | 2015-04-23 | Syngenta Participations Ag | 3-methanimidamid-pyridine derivatives as fungicides |
| US9750246B2 (en) | 2013-12-23 | 2017-09-05 | Syngenta Participations Ag | Insecticidal compounds |
| WO2015140071A1 (en) * | 2014-03-18 | 2015-09-24 | Bayer Cropscience Ag | Active compound combinations |
| WO2015181097A1 (en) * | 2014-05-28 | 2015-12-03 | Bayer Cropscience Ag | Process for preparing thiazole derivatives |
| CA2951177C (en) | 2014-06-25 | 2023-07-04 | BASF Agro B.V. | Pesticidal compositions |
| PL3214937T3 (pl) | 2014-11-07 | 2024-10-14 | Basf Se | Mieszaniny szkodnikobójcze |
| KR101673692B1 (ko) | 2014-11-07 | 2016-11-07 | 현대자동차주식회사 | 건식 실리카 입자를 포함하는 상변이 현탁 유체 조성물 및 이의 제조방법 |
| US10189799B2 (en) * | 2015-03-05 | 2019-01-29 | Bayer Cropscience Aktiengesellschaft | Process for preparing substituted phenylisoxazoline derivatives |
| CN105052945A (zh) * | 2015-09-09 | 2015-11-18 | 江苏省绿盾植保农药实验有限公司 | 一种含有氟吡菌胺和氟噻唑吡乙酮的杀菌剂组合物 |
| BR122022001869B1 (pt) * | 2015-12-10 | 2022-09-13 | Adama Makhteshim Ltd. | Composição de material agrícola, método de controle e prevenção de peste e de aperfeiçoamento do crescimento de planta, processo de preparo da composição de material agrícola e uso de um copolímero em bloco |
| BR112018015526A2 (pt) * | 2016-02-26 | 2018-12-26 | Basf Se | misturas fungicidas, composição fungicida, métodos para controlar fungos fitopatogênicos, para melhorar a saúde de plantas e para a proteção de material de propagação vegetal e material de propagação de plantas |
| RU2754614C2 (ru) | 2016-03-16 | 2021-09-03 | Басф Се | Применение тетразолинонов для борьбы с устойчивыми фитопатогенными грибами на злаковых культурах |
| CA3015456C (en) | 2016-03-16 | 2024-09-17 | Basf Se | USE OF TETRAZOLINONES TO CONTROL RESISTANT PLANT PATHOGENIC FUNGI ON FRUIT |
| US11241012B2 (en) | 2016-03-16 | 2022-02-08 | Basf Se | Use of tetrazolinones for combating resistant phytopathogenic fungi on soybean |
| KR101697258B1 (ko) * | 2016-09-05 | 2017-01-17 | 농업회사법인 주식회사 엘바이오텍 | 제독유황 분말 혼합물을 유효성분으로 함유하는 식물병 방제용 조성물 및 이의 용도 |
| EP3558956B1 (en) | 2016-12-20 | 2020-10-28 | Syngenta Participations AG | N-cyclobutyl-thiazol-5-carboxamides with nematicidal activity |
| KR101988442B1 (ko) * | 2017-06-30 | 2019-06-12 | 주식회사 삼양사 | 결정형 기능성 감미료 |
| CN109221163A (zh) * | 2017-07-10 | 2019-01-18 | 江苏龙灯化学有限公司 | 一种杀菌组合物 |
| CN109380241A (zh) * | 2017-08-07 | 2019-02-26 | 江苏龙灯化学有限公司 | 一种杀菌组合物 |
| US20190062173A1 (en) * | 2017-08-22 | 2019-02-28 | The Procter & Gamble Company | Process for making solid particles |
| WO2019048988A1 (en) | 2017-09-08 | 2019-03-14 | Pi Industries Ltd. | Novel fungidal heterocyclic compounds |
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| WO2021069700A1 (en) * | 2019-10-10 | 2021-04-15 | Myovant Sciences Gmbh | Crystalline solvated forms of n-(4-(1-(2,6-difluorobenzyl)-5- ((dimethylamino)methyl)-3-(6-methoxy-3-pyridazinyl)-2,4-dioxo-1,2,3,4- tetrahydrothieno[2,3-d]pyrimidin-6-yl)phenyl)-n'-methoxyurea |
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| GB9000130D0 (en) * | 1990-01-04 | 1990-03-07 | Ici Plc | Fungicides |
| GB0017617D0 (en) | 2000-07-18 | 2000-09-06 | Zeneca Ltd | Chemical process |
| US7598206B2 (en) * | 2004-12-23 | 2009-10-06 | Basf Aktiengesellschaft | Fungicidal mixtures |
| CN105165883B (zh) * | 2005-07-27 | 2018-01-30 | 巴斯夫欧洲公司 | 基于唑并嘧啶基胺的杀真菌混合物 |
| WO2008013622A2 (en) | 2006-07-27 | 2008-01-31 | E. I. Du Pont De Nemours And Company | Fungicidal azocyclic amides |
| TWI428091B (zh) | 2007-10-23 | 2014-03-01 | Du Pont | 殺真菌劑混合物 |
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