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
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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)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (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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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2516426B1 (de) | 2009-12-21 | 2015-09-16 | Bayer CropScience AG | Bis(difluormethyl)pyrazole als fungizide |
| US20130102631A1 (en) | 2010-07-02 | 2013-04-25 | Syngenta Crop Protection Llc | Novel microbiocidal dioxime ether derivatives |
| WO2012010567A1 (en) | 2010-07-19 | 2012-01-26 | Syngenta Participations Ag | Isoxazole, isothiazole, furane and thiophene compounds as microbicides |
| CN103003265A (zh) | 2010-07-19 | 2013-03-27 | 先正达参股股份有限公司 | 杀微生物剂 |
| AR082405A1 (es) | 2010-07-29 | 2012-12-05 | Syngenta Participations Ag | Derivados microbicidas de eteres de dioximas |
| EP2619181A1 (en) | 2010-09-23 | 2013-07-31 | Syngenta Participations AG | Novel microbiocides |
| AR083112A1 (es) | 2010-10-01 | 2013-01-30 | Syngenta Participations Ag | Metodo para controlar enfermedades fitopatogenas y composiciones fungicidas utiles para dicho control |
| JP5977242B2 (ja) * | 2010-10-07 | 2016-08-24 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | テトラゾリルオキシム誘導体とチアゾリルピペリジン誘導体を含んでいる殺菌剤組成物 |
| BR112013010336A2 (pt) | 2010-10-28 | 2016-07-05 | Syngenta Participations Ag | microbicidas |
| EP2638011A1 (en) | 2010-11-12 | 2013-09-18 | 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 |
| CN103221395A (zh) | 2010-11-23 | 2013-07-24 | 先正达参股股份有限公司 | 杀虫化合物 |
| WO2012069601A1 (en) | 2010-11-25 | 2012-05-31 | Syngenta Participations Ag | Substituted quinazolines as fungicides |
| CN103261188A (zh) | 2010-12-17 | 2013-08-21 | 先正达参股股份有限公司 | 杀虫化合物 |
| AR085318A1 (es) | 2011-02-09 | 2013-09-25 | Syngenta Participations Ag | Derivados de triazol que tienen actividad insecticida |
| WO2012117021A2 (en) | 2011-03-03 | 2012-09-07 | Syngenta Participations Ag | Novel microbiocidal oxime ethers |
| WO2012126881A1 (en) | 2011-03-22 | 2012-09-27 | Syngenta Participations Ag | Insecticidal compounds |
| 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 |
| AR087609A1 (es) | 2011-08-23 | 2014-04-03 | Syngenta Participations Ag | Microbiocidas |
| WO2013026900A1 (en) | 2011-08-23 | 2013-02-28 | Syngenta Participations Ag | Pyridine derivatives as microbiocides |
| WO2013037768A1 (de) | 2011-09-15 | 2013-03-21 | Bayer Intellectual Property Gmbh | Piperidinpyrazole als fungizide |
| EP2763966B1 (en) | 2011-10-03 | 2018-04-04 | Syngenta Participations AG | Insecticidal 2-methoxybenzamide derivatives |
| 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 |
| UY34426A (es) | 2011-11-04 | 2013-05-31 | Syngenta Participations Ag | Derivados de heteroarilcarboxamida, procesos de preparación, composiciones y sus usos en agricultura, veterinaria y control de plagas |
| BR112014010566A2 (pt) | 2011-11-04 | 2017-04-25 | Syngenta Participations Ag | compostos pesticidas |
| CN103930401B (zh) | 2011-11-04 | 2017-01-11 | 先正达参股股份有限公司 | 杀虫化合物 |
| EP2773631B1 (en) | 2011-11-04 | 2015-09-09 | 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 |
| US9718762B2 (en) | 2012-10-31 | 2017-08-01 | Syngenta Participations Ag | Insecticidal compounds |
| 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 |
| ES2746932T3 (es) | 2013-01-09 | 2020-03-09 | Basf Agro Bv | Proceso para la preparación de oxiranos y triazoles sustituidos |
| US9655363B2 (en) | 2013-02-04 | 2017-05-23 | Syngenta Participations Ag | Microbiocides |
| EP2961737B1 (en) | 2013-02-27 | 2017-07-26 | Syngenta Participations AG | Novel carboxamide compounds |
| BR112015025028B1 (pt) | 2013-04-02 | 2020-10-13 | Syngenta Participations Ag | compostos, processo para a produção de compostos, métodos para controle de insetos, ácaros, nematódeos ou moluscos e para proteção de plantas úteis e composição |
| WO2014161849A1 (en) | 2013-04-02 | 2014-10-09 | Syngenta Participations Ag | Insecticidal compounds |
| 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 |
| US10512267B2 (en) | 2013-07-08 | 2019-12-24 | BASF Agro, B.V. | Compositions comprising a triazole compound and a biopesticide |
| AU2014289431B2 (en) | 2013-07-08 | 2018-01-18 | Syngenta Crop Protection Ag | 4-membered ring carboxamides used as nematicides |
| WO2015006545A1 (en) * | 2013-07-12 | 2015-01-15 | Valent U.S.A. Corporation | Pesticidal dispersible concentrate formulations |
| 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 |
| 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 |
| CN113575594B (zh) * | 2013-10-03 | 2022-10-04 | 先正达参股股份有限公司 | 杀真菌组合物 |
| MX361771B (es) * | 2013-10-17 | 2018-12-17 | Bayer Cropscience Ag | Forma cristalina novedosa de 2-{3-[2-(1-{[3,5-bis(difluorometil)-1 h-pirazol-1-il]acetil}piperidin-4-il)-1,3-tiazol-4-il]-4,5-dihidr o-1,2-oxazol-5-il}-3-clorofenilmetanosulfonato. |
| WO2015055764A1 (en) | 2013-10-18 | 2015-04-23 | Syngenta Participations Ag | 3-methanimidamid-pyridine derivatives as fungicides |
| AU2014372693A1 (en) | 2013-12-23 | 2016-06-16 | Syngenta Participations Ag | Insecticidal compounds |
| WO2015140071A1 (en) * | 2014-03-18 | 2015-09-24 | Bayer Cropscience Ag | Active compound combinations |
| BR112016027819B1 (pt) * | 2014-05-28 | 2023-05-02 | Bayer Cropscience Aktiengesellschaft | Processo de preparação de derivados de tiazole |
| AU2015281187B2 (en) | 2014-06-25 | 2018-10-04 | BASF Agro B.V. | Pesticidal compositions |
| BR112017009282A2 (pt) | 2014-11-07 | 2018-01-30 | Basf Se | misturas fungicidas, composição pesticida, métodos para controlar pragas fitopatogênicas, para melhorar a fitossanidade e para proteção de material de propagação de plantas contra pragas, e, material de propagação de plantas. |
| KR101673692B1 (ko) * | 2014-11-07 | 2016-11-07 | 현대자동차주식회사 | 건식 실리카 입자를 포함하는 상변이 현탁 유체 조성물 및 이의 제조방법 |
| DK3265446T3 (da) | 2015-03-05 | 2019-10-28 | Bayer Cropscience Ag | Fremgangsmåde til fremstilling af substituerede phenylisoxazolinderivater |
| 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 |
| US20170172142A1 (en) * | 2015-12-10 | 2017-06-22 | Adama Makhteshim Ltd. | Polyelectrolyte-layer forming block copolymers and compositions and uses thereof |
| EP3419423A1 (en) * | 2016-02-26 | 2019-01-02 | Basf Se | Fungicidal mixtures comprising fluxapyroxad |
| BR112018068705B1 (pt) | 2016-03-16 | 2022-09-06 | Basf Se | Método para controlar fungos fitopatogênicos |
| CA3015744C (en) | 2016-03-16 | 2024-04-23 | Basf Se | Use of 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one for combating resistant phytopathogenic fungi on cereals |
| EP3429358A1 (en) | 2016-03-16 | 2019-01-23 | Basf Se | Use of tetrazolinones for combating resistant phytopathogenic fungi on fruits |
| KR101697258B1 (ko) * | 2016-09-05 | 2017-01-17 | 농업회사법인 주식회사 엘바이오텍 | 제독유황 분말 혼합물을 유효성분으로 함유하는 식물병 방제용 조성물 및 이의 용도 |
| WO2018114657A1 (en) | 2016-12-20 | 2018-06-28 | 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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| EP3982731A4 (en) * | 2019-06-15 | 2023-07-19 | JDM Scientific Research Organisation Private Limited | SYNERGISTIC FUNGICIDE COMPOSITION |
| BR112022000352A2 (pt) * | 2019-07-10 | 2022-05-10 | Gharda Chemicals Ltd | Processo para isolar cristais de isômero s de indoxacarbe |
| JP7713934B2 (ja) * | 2019-10-10 | 2025-07-28 | スミトモ ファーマ スウィッツァーランド ゲーエムベーハー | Ｎ－（４－（１－（２，６－ジフルオロベンジル）－５－（（ジメチルアミノ）メチル）－３－（６－メトキシ－３－ピリダジニル）－２，４－ジオキソ－１，２，３，４－テトラヒドロチエノ［２，３－ｄ］ピリミジン－６－イル）フェニル）－Ｎ’－メトキシ尿素の結晶溶媒和形 |
| JP2022551316A (ja) | 2019-10-10 | 2022-12-08 | ミオバント サイエンシズ ゲーエムベーハー | Ｎ－（４－（１－（２，６－ジフルオロベンジル）－５－（（ジメチルアミノ）メチル）－３－（６－メトキシ－３－ピリダジニル）－２，４－ジオキソ－１，２，３，４－テトラヒドロチエノ［２，３－ｄ］ピリミジン－６－イル）フェニル）－Ｎ’－メトキシ尿素の結晶形 |
| CN111357751A (zh) * | 2020-04-24 | 2020-07-03 | 青岛科技大学 | 一种含氟噻唑吡乙酮和丙氧喹啉的杀菌组合物 |
| CN111357746A (zh) * | 2020-04-24 | 2020-07-03 | 青岛科技大学 | 一种含氟噻唑吡乙酮和苯氧喹啉的杀菌组合物 |
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| US20240180159A1 (en) * | 2021-03-17 | 2024-06-06 | Syngenta Crop Protection Ag | New oil suspension concentrate composition |
| US20240196895A1 (en) * | 2021-03-30 | 2024-06-20 | Syngenta Crop Protection Ag | Formulation |
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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 |
| CN101822260A (zh) * | 2004-12-23 | 2010-09-08 | 巴斯夫欧洲公司 | 杀真菌混合物 |
| US8679514B2 (en) * | 2005-07-27 | 2014-03-25 | Basf Se | Fungicidal mixtures based on azolopyrimidinylamines |
| 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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