JP2015518023A5 - - Google Patents
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- Publication number
- JP2015518023A5 JP2015518023A5 JP2015514476A JP2015514476A JP2015518023A5 JP 2015518023 A5 JP2015518023 A5 JP 2015518023A5 JP 2015514476 A JP2015514476 A JP 2015514476A JP 2015514476 A JP2015514476 A JP 2015514476A JP 2015518023 A5 JP2015518023 A5 JP 2015518023A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- carboxamide
- pyrazole
- biphenyl
- trifluoromethyl
- 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.)
- Granted
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- 239000003112 inhibitor Substances 0.000 claims 17
- -1 benazole Chemical class 0.000 claims 15
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims 14
- 244000063299 Bacillus subtilis Species 0.000 claims 10
- 235000014469 Bacillus subtilis Nutrition 0.000 claims 10
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 8
- 102000000452 Acetyl-CoA carboxylase Human genes 0.000 claims 7
- 108010016219 Acetyl-CoA carboxylase Proteins 0.000 claims 7
- 108010018763 Biotin carboxylase Proteins 0.000 claims 7
- 230000000855 fungicidal effect Effects 0.000 claims 6
- 239000000417 fungicide Substances 0.000 claims 6
- 241000238876 Acari Species 0.000 claims 4
- 241000238631 Hexapoda Species 0.000 claims 4
- 241000244206 Nematoda Species 0.000 claims 4
- 230000000853 biopesticidal effect Effects 0.000 claims 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 4
- 239000002917 insecticide Substances 0.000 claims 4
- 235000005152 nicotinamide Nutrition 0.000 claims 4
- 239000011570 nicotinamide Substances 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 241000194103 Bacillus pumilus Species 0.000 claims 3
- 241000635201 Pumilus Species 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 244000000003 plant pathogen Species 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 235000013311 vegetables Nutrition 0.000 claims 3
- RUXHWBMJNBBYNL-UHFFFAOYSA-N 3-hydroxy-1,2-dihydropyrrol-5-one Chemical class OC1=CC(=O)NC1 RUXHWBMJNBBYNL-UHFFFAOYSA-N 0.000 claims 2
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 claims 2
- LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 239000005664 Spirodiclofen Substances 0.000 claims 2
- 239000005665 Spiromesifen Substances 0.000 claims 2
- 239000005931 Spirotetramat Substances 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 claims 2
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 claims 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims 2
- 235000013399 edible fruits Nutrition 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 230000001747 exhibiting effect Effects 0.000 claims 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 2
- 239000002207 metabolite Substances 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- PEQJBOMPGWYIRO-UHFFFAOYSA-N n-ethyl-3,4-dimethoxyaniline Chemical class CCNC1=CC=C(OC)C(OC)=C1 PEQJBOMPGWYIRO-UHFFFAOYSA-N 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims 2
- JGCSKOVQDXEQHI-UHFFFAOYSA-N phenazine-1-carboxylic acid Chemical compound C1=CC=C2N=C3C(C(=O)O)=CC=CC3=NC2=C1 JGCSKOVQDXEQHI-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- QJBZDBLBQWFTPZ-UHFFFAOYSA-N pyrrolnitrin Chemical compound [O-][N+](=O)C1=C(Cl)C=CC=C1C1=CNC=C1Cl QJBZDBLBQWFTPZ-UHFFFAOYSA-N 0.000 claims 2
- 230000035806 respiratory chain Effects 0.000 claims 2
- DTDSAWVUFPGDMX-UHFFFAOYSA-N spirodiclofen Chemical compound CCC(C)(C)C(=O)OC1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC11CCCCC1 DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 claims 2
- GOLXNESZZPUPJE-UHFFFAOYSA-N spiromesifen Chemical compound CC1=CC(C)=CC(C)=C1C(C(O1)=O)=C(OC(=O)CC(C)(C)C)C11CCCC1 GOLXNESZZPUPJE-UHFFFAOYSA-N 0.000 claims 2
- CLSVJBIHYWPGQY-GGYDESQDSA-N spirotetramat Chemical compound CCOC(=O)OC1=C(C=2C(=CC=C(C)C=2)C)C(=O)N[C@@]11CC[C@H](OC)CC1 CLSVJBIHYWPGQY-GGYDESQDSA-N 0.000 claims 2
- SBNFWQZLDJGRLK-RTWAWAEBSA-N (1R)-trans-phenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-RTWAWAEBSA-N 0.000 claims 1
- XDEHMKQLKPZERH-BYPYZUCNSA-N (2s)-2-amino-3-methylbutanamide Chemical compound CC(C)[C@H](N)C(N)=O XDEHMKQLKPZERH-BYPYZUCNSA-N 0.000 claims 1
- AESOVJYUXGEHCV-UHFFFAOYSA-N (5-bromo-2-methoxy-4-methylpyridin-3-yl)-(2,3,4-trimethoxy-6-methylphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C)=C1C(=O)C1=C(C)C(Br)=CN=C1OC AESOVJYUXGEHCV-UHFFFAOYSA-N 0.000 claims 1
- IAQLCKZJGNTRDO-LJQANCHMSA-N (R)-oxathiapiprolin Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2C[C@@H](ON=2)C=2C(=CC=CC=2F)F)CC1 IAQLCKZJGNTRDO-LJQANCHMSA-N 0.000 claims 1
- 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 1
- XODZOJBRMYSETR-UHFFFAOYSA-N 2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4-one Chemical compound O=C1N(CCCC)C(CCCC)=NC2=C1C=C(Cl)S2 XODZOJBRMYSETR-UHFFFAOYSA-N 0.000 claims 1
- DNBMPXLFKQCOBV-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl n-(1h-benzimidazol-2-yl)carbamate Chemical compound C1=CC=C2NC(NC(=O)OCCOCCOCC)=NC2=C1 DNBMPXLFKQCOBV-UHFFFAOYSA-N 0.000 claims 1
- QKJJCZYFXJCKRX-HZHKWBLPSA-N 2-[(2s,3s,6r)-6-[4-amino-5-(hydroxymethyl)-2-oxopyrimidin-1-yl]-3-[[(2s)-2-amino-3-hydroxypropanoyl]amino]-3,6-dihydro-2h-pyran-2-yl]-5-(diaminomethylideneamino)-2,4-dihydroxypentanoic acid Chemical compound O1[C@H](C(O)(CC(O)CN=C(N)N)C(O)=O)[C@@H](NC(=O)[C@H](CO)N)C=C[C@@H]1N1C(=O)N=C(N)C(CO)=C1 QKJJCZYFXJCKRX-HZHKWBLPSA-N 0.000 claims 1
- MQFJRLQNQOJQEI-HXUWFJFHSA-N 2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-1-[4-[4-[(5r)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2C[C@@H](ON=2)C=2C=CC=CC=2)CC1 MQFJRLQNQOJQEI-HXUWFJFHSA-N 0.000 claims 1
- MQFJRLQNQOJQEI-FQEVSTJZSA-N 2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-1-[4-[4-[(5s)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound CC1=CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2C[C@H](ON=2)C=2C=CC=CC=2)CC1 MQFJRLQNQOJQEI-FQEVSTJZSA-N 0.000 claims 1
- ZQMRDENWZKMOTM-UHFFFAOYSA-N 2-butoxy-6-iodo-3-propylchromen-4-one Chemical compound C1=C(I)C=C2C(=O)C(CCC)=C(OCCCC)OC2=C1 ZQMRDENWZKMOTM-UHFFFAOYSA-N 0.000 claims 1
- URSDKQVCLKINOM-UHFFFAOYSA-N 2-chloro-5-[2-chloro-3-(2,6-difluoro-4-methoxyphenyl)-5-methylimidazol-4-yl]pyridine Chemical compound FC1=CC(OC)=CC(F)=C1N1C(C=2C=NC(Cl)=CC=2)=C(C)N=C1Cl URSDKQVCLKINOM-UHFFFAOYSA-N 0.000 claims 1
- 229940061334 2-phenylphenol Drugs 0.000 claims 1
- ZVOWUYIDRJPVTD-UHFFFAOYSA-N 3,4,5-trichloropyridine-2,6-dicarbonitrile Chemical compound ClC1=C(Cl)C(C#N)=NC(C#N)=C1Cl ZVOWUYIDRJPVTD-UHFFFAOYSA-N 0.000 claims 1
- OSRHUTRVDLFDRE-UHFFFAOYSA-N 3-(4,4,5-trifluoro-3,3-dimethylisoquinolin-1-yl)-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)C(C3=NC(C(C4=C(F)C=CC=C43)(F)F)(C)C)=CC2=C1 OSRHUTRVDLFDRE-UHFFFAOYSA-N 0.000 claims 1
- JQNKSCBHXQAMHB-UHFFFAOYSA-N 3-(difluoromethyl)-n-[2-(4-ethynylphenyl)phenyl]-1-methylpyrazole-4-carboxamide Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(C#C)C=C1 JQNKSCBHXQAMHB-UHFFFAOYSA-N 0.000 claims 1
- DHTJFQWHCVTNRY-UHFFFAOYSA-N 3-[5-(4-chlorophenyl)-2,3-dimethyl-1,2-oxazolidin-3-yl]pyridine Chemical compound CN1OC(C=2C=CC(Cl)=CC=2)CC1(C)C1=CC=CN=C1 DHTJFQWHCVTNRY-UHFFFAOYSA-N 0.000 claims 1
- DNDLJUVNJLTMIE-UHFFFAOYSA-N 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine Chemical compound C=1C=C(Cl)C=CC=1C=1C(C)=NN=C(Cl)C=1C1=C(F)C=CC=C1F DNDLJUVNJLTMIE-UHFFFAOYSA-N 0.000 claims 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
- ZMYKITJYWFYRFJ-UHFFFAOYSA-N 4-oxo-4-(2-phenylethylamino)butanoic acid Chemical compound OC(=O)CCC(=O)NCCC1=CC=CC=C1 ZMYKITJYWFYRFJ-UHFFFAOYSA-N 0.000 claims 1
- GDGIVSREGUOIJZ-UHFFFAOYSA-N 5-amino-3h-1,3,4-thiadiazole-2-thione Chemical compound NC1=NN=C(S)S1 GDGIVSREGUOIJZ-UHFFFAOYSA-N 0.000 claims 1
- QKRORLUXLQYKAA-UHFFFAOYSA-N 5-chloro-n'-phenyl-n'-prop-2-ynylthiophene-2-sulfonohydrazide Chemical compound S1C(Cl)=CC=C1S(=O)(=O)NN(CC#C)C1=CC=CC=C1 QKRORLUXLQYKAA-UHFFFAOYSA-N 0.000 claims 1
- ZALZMUXMSIVXKA-UHFFFAOYSA-N 5-fluoro-2-[(4-fluorophenyl)methoxy]pyrimidin-4-amine Chemical compound C1=C(F)C(N)=NC(OCC=2C=CC(F)=CC=2)=N1 ZALZMUXMSIVXKA-UHFFFAOYSA-N 0.000 claims 1
- 230000002407 ATP formation Effects 0.000 claims 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
- HZRCGNGZXKSBNZ-UHFFFAOYSA-N CC1=NC=2N(C(=C1CCCCCCCC)N)N=CN2.FC=2C(=NC(=NC2)OCC2=CC=C(C=C2)C)N Chemical compound CC1=NC=2N(C(=C1CCCCCCCC)N)N=CN2.FC=2C(=NC(=NC2)OCC2=CC=C(C=C2)C)N HZRCGNGZXKSBNZ-UHFFFAOYSA-N 0.000 claims 1
- 239000005973 Carvone Substances 0.000 claims 1
- 239000005644 Dazomet Substances 0.000 claims 1
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 claims 1
- 102000015782 Electron Transport Complex III Human genes 0.000 claims 1
- 108010024882 Electron Transport Complex III Proteins 0.000 claims 1
- 239000005779 Fenpyrazamine Substances 0.000 claims 1
- 239000005780 Fluazinam Substances 0.000 claims 1
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims 1
- 239000005847 Triazoxide Substances 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 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 1
- 239000004067 bulking agent Substances 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 230000032823 cell division Effects 0.000 claims 1
- 239000002577 cryoprotective agent Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- ACMXQHFNODYQAT-UHFFFAOYSA-N cyflufenamid Chemical compound FC1=CC=C(C(F)(F)F)C(C(NOCC2CC2)=NC(=O)CC=2C=CC=CC=2)=C1F ACMXQHFNODYQAT-UHFFFAOYSA-N 0.000 claims 1
- OAWUUPVZMNKZRY-UHFFFAOYSA-N cyprosulfamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NC2CC2)C=C1 OAWUUPVZMNKZRY-UHFFFAOYSA-N 0.000 claims 1
- NMCCNOZOBBWFMN-UHFFFAOYSA-N davicil Chemical compound CS(=O)(=O)C1=C(Cl)C(Cl)=NC(Cl)=C1Cl NMCCNOZOBBWFMN-UHFFFAOYSA-N 0.000 claims 1
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 claims 1
- 230000007123 defense Effects 0.000 claims 1
- 229960003887 dichlorophen Drugs 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 239000002270 dispersing agent Substances 0.000 claims 1
- 239000003995 emulsifying agent Substances 0.000 claims 1
- 230000008686 ergosterol biosynthesis Effects 0.000 claims 1
- UTOHZQYBSYOOGC-UHFFFAOYSA-N fenpyrazamine Chemical compound O=C1N(C(C)C)N(C(=O)SCC=C)C(N)=C1C1=CC=CC=C1C UTOHZQYBSYOOGC-UHFFFAOYSA-N 0.000 claims 1
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 claims 1
- 235000021022 fresh fruits Nutrition 0.000 claims 1
- 238000003306 harvesting Methods 0.000 claims 1
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 230000008099 melanin synthesis Effects 0.000 claims 1
- 239000012528 membrane Substances 0.000 claims 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- KCIRYJNISRMYFI-UHFFFAOYSA-N mildiomycin Natural products NC(CO)C(=O)NC1C=CC(OC1C(O)(CC(O)CNC(=N)N)C(=O)O)N2CN=C(N)C(=C2)CO KCIRYJNISRMYFI-UHFFFAOYSA-N 0.000 claims 1
- 230000011278 mitosis Effects 0.000 claims 1
- CDXKAMHMYQAUSW-UHFFFAOYSA-N n'-[4-[(3-tert-butyl-4-cyano-1,2-thiazol-5-yl)oxy]-2-chloro-5-methylphenyl]-n-ethyl-n-methylmethanimidamide Chemical compound C1=C(Cl)C(N=CN(C)CC)=CC(C)=C1OC1=C(C#N)C(C(C)(C)C)=NS1 CDXKAMHMYQAUSW-UHFFFAOYSA-N 0.000 claims 1
- BLCKKNLGFULNRC-UHFFFAOYSA-L n,n-dimethylcarbamodithioate;nickel(2+) Chemical compound [Ni+2].CN(C)C([S-])=S.CN(C)C([S-])=S BLCKKNLGFULNRC-UHFFFAOYSA-L 0.000 claims 1
- GCIZLUZYQSYVSS-UHFFFAOYSA-N n-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloropyridine-3-carboxamide Chemical compound ClC1=CC=NC(Cl)=C1C(=O)NCC1=NC=C(Br)C=C1Cl GCIZLUZYQSYVSS-UHFFFAOYSA-N 0.000 claims 1
- HQUIFHINFGFWLJ-UHFFFAOYSA-N n-[(cyclopropylmethoxyamino)-[6-(difluoromethoxy)-2,3-difluorophenyl]methylidene]-2-phenylacetamide Chemical compound FC(F)OC1=CC=C(F)C(F)=C1C(NOCC1CC1)=NC(=O)CC1=CC=CC=C1 HQUIFHINFGFWLJ-UHFFFAOYSA-N 0.000 claims 1
- RRRNUBCOWJALGN-UHFFFAOYSA-N n-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloropyridine-3-carboxamide Chemical compound N=1C=C(Br)C=C(Cl)C=1C(C)NC(=O)C1=C(Cl)C=CN=C1Cl RRRNUBCOWJALGN-UHFFFAOYSA-N 0.000 claims 1
- PFOUYPVSYHSBMI-UHFFFAOYSA-N n-[2-(4-ethynylphenyl)phenyl]-5-fluoro-1,3-dimethylpyrazole-4-carboxamide Chemical compound CC1=NN(C)C(F)=C1C(=O)NC1=CC=CC=C1C1=CC=C(C#C)C=C1 PFOUYPVSYHSBMI-UHFFFAOYSA-N 0.000 claims 1
- AHJKPWGTBVOQFA-UHFFFAOYSA-N n-methyl-2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-n-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,3-thiazole-4-carboxamide Chemical compound C1CCC2=CC=CC=C2C1N(C)C(=O)C(N=1)=CSC=1C(CC1)CCN1C(=O)CN1N=C(C(F)(F)F)C=C1C AHJKPWGTBVOQFA-UHFFFAOYSA-N 0.000 claims 1
- AHJKPWGTBVOQFA-QFIPXVFZSA-N n-methyl-2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-n-[(1s)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide Chemical compound CN([C@@H]1C2=CC=CC=C2CCC1)C(=O)C(N=1)=CSC=1C(CC1)CCN1C(=O)CN1N=C(C(F)(F)F)C=C1C AHJKPWGTBVOQFA-QFIPXVFZSA-N 0.000 claims 1
- 235000010298 natamycin Nutrition 0.000 claims 1
- 229960003255 natamycin Drugs 0.000 claims 1
- NCXMLFZGDNKEPB-FFPOYIOWSA-N natamycin Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C[C@@H](C)OC(=O)/C=C/[C@H]2O[C@@H]2C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 NCXMLFZGDNKEPB-FFPOYIOWSA-N 0.000 claims 1
- 239000004311 natamycin Substances 0.000 claims 1
- 238000001668 nucleic acid synthesis Methods 0.000 claims 1
- 235000010292 orthophenyl phenol Nutrition 0.000 claims 1
- 239000000575 pesticide Substances 0.000 claims 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
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- BAUQXSYUDSNRHL-UHFFFAOYSA-N pyrimorph Chemical compound C1=CC(C(C)(C)C)=CC=C1C(C=1C=NC(Cl)=CC=1)=CC(=O)N1CCOCC1 BAUQXSYUDSNRHL-UHFFFAOYSA-N 0.000 claims 1
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- IYYIUOWKEMQYNV-UHFFFAOYSA-N sodium;ethoxy-oxido-oxophosphanium Chemical compound [Na+].CCO[P+]([O-])=O IYYIUOWKEMQYNV-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
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- URHWNXDZOULUHC-UHFFFAOYSA-N tert-butyl n-[6-[[[(1-methyltetrazol-5-yl)-phenylmethylidene]amino]oxymethyl]pyridin-2-yl]carbamate Chemical compound CN1N=NN=C1C(C=1C=CC=CC=1)=NOCC1=CC=CC(NC(=O)OC(C)(C)C)=N1 URHWNXDZOULUHC-UHFFFAOYSA-N 0.000 claims 1
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| US10306889B2 (en) | 2012-05-30 | 2019-06-04 | Bayer Cropscience Ag | Compositions comprising a biological control agent and an insecticide |
| AU2013269661B2 (en) | 2012-05-30 | 2016-10-27 | Bayer Cropscience Ag | Compositions comprising a biological control agent and an insecticide |
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| KR102095974B1 (ko) | 2012-05-30 | 2020-04-02 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 생물학적 방제제 및 살곤충제를 포함하는 조성물 |
| BR112014029224A2 (pt) | 2012-05-30 | 2017-06-27 | Bayer Cropscience Ag | composição que compreende um agente de controle biológico e um fungicida |
| KR102095979B1 (ko) | 2012-05-30 | 2020-04-02 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 생물학적 방제제 및 살곤충제를 포함하는 조성물 |
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| US9968097B2 (en) | 2012-05-30 | 2018-05-15 | Bayer Cropscience Ag | Composition comprising a biological control agent and a fungicide selected from inhibitors of the lipid membrane synthesis, the melanine biosynthesis, the nucleic acid synthesis or the signal transduction |
| MX373820B (es) | 2012-05-30 | 2020-03-24 | Bayer Cropscience Ag | Una composición que comprende un agente de control biológico y un fungicida seleccionado de inhibidores de la mitosis y la división celular y compuestos capaces de tener una acción en múltiples sitios. |
| NZ742943A (en) | 2012-05-30 | 2019-04-26 | Bayer Cropscience Ag | Compositions comprising a biological control agent and a fungicide from the group consisting of inhibitors of the respiratory chain at complex i or ii |
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2013
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- 2013-05-29 MX MX2014014121A patent/MX360058B/es active IP Right Grant
- 2013-05-29 US US14/404,018 patent/US9398770B2/en active Active
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- 2013-05-29 JP JP2015514476A patent/JP6130909B2/ja not_active Expired - Fee Related
- 2013-05-29 CN CN201710146020.3A patent/CN106962403B/zh not_active Expired - Fee Related
- 2013-05-29 IN IN9358DEN2014 patent/IN2014DN09358A/en unknown
- 2013-05-29 NZ NZ725224A patent/NZ725224A/en not_active IP Right Cessation
- 2013-05-29 CN CN201380029033.2A patent/CN104363758B/zh not_active Expired - Fee Related
- 2013-05-29 KR KR1020147033190A patent/KR102095976B1/ko not_active Expired - Fee Related
- 2013-05-29 EP EP13726744.9A patent/EP2854532B1/en active Active
- 2013-05-29 ES ES13726744T patent/ES2748624T3/es active Active
- 2013-05-29 BR BR112014029123A patent/BR112014029123A2/pt not_active Application Discontinuation
- 2013-05-29 WO PCT/EP2013/061033 patent/WO2013178663A1/en not_active Ceased
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2014
- 2014-11-04 IL IL235492A patent/IL235492A/en not_active IP Right Cessation
- 2014-11-19 CO CO14254017A patent/CO7310525A2/es unknown
- 2014-11-27 PH PH12014502653A patent/PH12014502653A1/en unknown
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2016
- 2016-06-21 US US15/187,817 patent/US9737078B2/en not_active Expired - Fee Related
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2017
- 2017-06-22 IL IL253138A patent/IL253138A0/en unknown
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