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
- 229960003536 phenothrin Drugs 0.000 claims 1
- 230000008635 plant growth Effects 0.000 claims 1
- 230000004260 plant-type cell wall biogenesis Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 235000010388 propyl gallate Nutrition 0.000 claims 1
- 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
- 229960002132 pyrrolnitrin Drugs 0.000 claims 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims 1
- MRUMAIRJPMUAPZ-UHFFFAOYSA-N quinolin-8-ol;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CN=C2C(O)=CC=CC2=C1 MRUMAIRJPMUAPZ-UHFFFAOYSA-N 0.000 claims 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 claims 1
- 230000019491 signal transduction Effects 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 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
- 230000002269 spontaneous effect Effects 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 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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- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 claims 1
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| WO2013178661A1 (en) | 2012-05-30 | 2013-12-05 | Bayer Cropscience Ag | Compositiions comprising a biological control agent and an insecticide |
| EP2854535A1 (en) | 2012-05-30 | 2015-04-08 | Bayer Cropscience AG | Compositions comprising a biological control agent and an insecticide |
| CN107027809A (zh) | 2012-05-30 | 2017-08-11 | 拜耳作物科学股份公司 | 包含生物防治剂和选自呼吸链复合物i或ii抑制剂的杀真菌剂的组合物 |
| EP2854536A1 (en) | 2012-05-30 | 2015-04-08 | Bayer Cropscience AG | Compositions comprising a biological control agent and an insecticide |
| WO2013178658A1 (en) | 2012-05-30 | 2013-12-05 | Bayer Cropscience Ag | Compositions comprising a biological control agent and an insecticide |
| EP3281526A1 (en) | 2012-05-30 | 2018-02-14 | Bayer CropScience Aktiengesellschaft | Composition comprising a biological control agent and a fungicide |
| NZ725994A (en) | 2012-05-30 | 2018-07-27 | Bayer Cropscience Ag | Composition comprising a biological control agent and a fungicide selected from inhibitors of the ergosterol biosynthesis |
| EP2854529B1 (en) | 2012-05-30 | 2018-01-17 | Bayer Cropscience AG | Compositions comprising a biological control agent and an insecticide |
| KR20150023475A (ko) | 2012-05-30 | 2015-03-05 | 바이엘 크롭사이언스 아게 | 생물학적 방제제, 및 지질막 합성, 멜라닌 생합성, 핵산 합성 또는 신호 전달의 억제제로부터 선택된 살진균제를 포함하는 조성물 |
| PT2854552T (pt) | 2012-05-30 | 2019-07-25 | Bayer Cropscience Ag | Composição compreendendo um agente de controlo biológico e um fungicida selecionado a partir de inibidores da biossíntese de aminoácidos ou proteínas, inibidores da produção de atp e inibidores da síntese da parede celular |
| WO2014071182A1 (en) | 2012-11-01 | 2014-05-08 | Massachusetts Institute Of Technology | Directed evolution of synthetic gene cluster |
| CN104974100A (zh) * | 2015-07-07 | 2015-10-14 | 江苏省农业科学院 | 来源于抗生素溶杆菌oh13的吩嗪类化合物及其制备方法与应用 |
| KR102804055B1 (ko) * | 2015-07-13 | 2025-05-08 | 피벗 바이오, 인크. | 식물 형질 개선을 위한 방법 및 조성물 |
| CN105002120B (zh) * | 2015-08-14 | 2018-01-30 | 潍坊万胜生物农药有限公司 | 一株蕈状芽孢杆菌及其应用 |
| CA3001001A1 (en) | 2015-10-05 | 2017-04-13 | Massachusetts Institute Of Technology | Nitrogen fixation using refactored nif clusters |
| CN107142226B (zh) * | 2016-03-01 | 2020-09-22 | 中国科学院武汉病毒研究所 | 一种枯草芽胞杆菌atr2及制备方法和应用 |
| JP6824519B2 (ja) * | 2016-09-29 | 2021-02-03 | 公立大学法人秋田県立大学 | ダイズ黒根腐病防除剤、ダイズ黒根腐病を抑制する微生物資材、及びダイズ黒根腐病防除方法 |
| CN106538604A (zh) * | 2016-09-30 | 2017-03-29 | 赵青娇 | 一种含吡唑萘菌胺的杀菌剂 |
| CN116904333A (zh) | 2017-01-12 | 2023-10-20 | 皮沃特生物公司 | 用于改良植物性状的方法及组合物 |
| BR122023022721A2 (pt) * | 2017-03-24 | 2023-12-26 | Novozymes Bioag A/S | Composição que compreende quantidades sinergicamente eficazes de yersinia entomophaga, ou um filtrado isento de células da mesma, e um inseticida químico; e método |
| CN111201234A (zh) * | 2017-07-17 | 2020-05-26 | 南京瑞捷医药科技有限公司 | 新型化合物及其作为acc抑制剂的用途 |
| MX2020004343A (es) | 2017-10-25 | 2021-01-08 | Pivot Bio Inc | Métodos y composiciones para mejorar microbios modificados que fijan nitrógeno. |
| CN111527057A (zh) | 2017-10-25 | 2020-08-11 | 皮沃特生物股份有限公司 | 靶向改良植物性状的固氮的基因靶标 |
| CN111394274B (zh) * | 2017-11-03 | 2021-10-22 | 南京农业大学 | 降解杀虫剂噻嗪酮和联苯菊酯的菌剂及其应用 |
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| WO2020065025A1 (en) | 2018-09-28 | 2020-04-02 | Bayer Aktiengesellschaft | Combination of bacterial biological control agent and fatty acids |
| WO2020190363A1 (en) | 2019-03-19 | 2020-09-24 | Massachusetts Institute Of Technology | Control of nitrogen fixation in rhizobia that associate with cereals |
| CA3129539A1 (en) | 2019-04-25 | 2020-10-29 | Min-Hyung RYU | High-throughput methods for isolating and characterizing ammonium-excreting mutant libraries generated by chemical mutagenesis |
| CN110200067B (zh) * | 2019-07-08 | 2021-08-27 | 桂林理工大学 | 一种黄秋葵的保鲜方法 |
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| CN116334021B (zh) * | 2023-03-30 | 2026-02-03 | 上海交通大学 | 一种多杀菌素酰基转移酶突变体及其应用 |
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| WO2011154494A2 (en) * | 2010-06-09 | 2011-12-15 | Syngenta Participations Ag | Pesticidal mixtures comprising isoxazoline derivatives |
| EP2651220A1 (en) | 2010-12-15 | 2013-10-23 | Syngenta Participations AG | Pesticidal mixtures |
| PE20141468A1 (es) | 2010-12-21 | 2014-11-05 | Bayer Cropscience Lp | Mutantes tipo papel de lija de bacillus y metodos de uso de los mismo para mejorar el crecimiento vegetal, promover la salud de plantas y controlar enfermedades y plagas |
| EP3281526A1 (en) | 2012-05-30 | 2018-02-14 | Bayer CropScience Aktiengesellschaft | Composition comprising a biological control agent and a fungicide |
| KR20150023475A (ko) | 2012-05-30 | 2015-03-05 | 바이엘 크롭사이언스 아게 | 생물학적 방제제, 및 지질막 합성, 멜라닌 생합성, 핵산 합성 또는 신호 전달의 억제제로부터 선택된 살진균제를 포함하는 조성물 |
| TR201816257T4 (tr) | 2012-05-30 | 2018-11-21 | Bayer Cropscience Ag | Bir biyolojik kontrol ajanı ve trifloksistrobin içeren bileşim. |
| WO2013178658A1 (en) | 2012-05-30 | 2013-12-05 | Bayer Cropscience Ag | Compositions comprising a biological control agent and an insecticide |
| WO2013178660A1 (en) | 2012-05-30 | 2013-12-05 | Bayer Cropscience Ag | Compositions comprising a biological control agent and an insecticide |
| EP2854535A1 (en) | 2012-05-30 | 2015-04-08 | Bayer Cropscience AG | Compositions comprising a biological control agent and an insecticide |
| EP2854529B1 (en) | 2012-05-30 | 2018-01-17 | Bayer Cropscience AG | Compositions comprising a biological control agent and an insecticide |
| WO2013178661A1 (en) | 2012-05-30 | 2013-12-05 | Bayer Cropscience Ag | Compositiions comprising a biological control agent and an insecticide |
| PT2854552T (pt) | 2012-05-30 | 2019-07-25 | Bayer Cropscience Ag | Composição compreendendo um agente de controlo biológico e um fungicida selecionado a partir de inibidores da biossíntese de aminoácidos ou proteínas, inibidores da produção de atp e inibidores da síntese da parede celular |
| HRP20181752T1 (hr) | 2012-05-30 | 2018-12-28 | Bayer Cropscience Ag | Pripravak koji sadrži biološko kontrolno sredstvo i fluopikolid |
| NZ725994A (en) | 2012-05-30 | 2018-07-27 | Bayer Cropscience Ag | Composition comprising a biological control agent and a fungicide selected from inhibitors of the ergosterol biosynthesis |
| EP2854536A1 (en) | 2012-05-30 | 2015-04-08 | Bayer Cropscience AG | Compositions comprising a biological control agent and an insecticide |
| CN107027809A (zh) | 2012-05-30 | 2017-08-11 | 拜耳作物科学股份公司 | 包含生物防治剂和选自呼吸链复合物i或ii抑制剂的杀真菌剂的组合物 |
-
2013
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- 2013-05-29 CN CN201710146020.3A patent/CN106962403B/zh not_active Expired - Fee Related
- 2013-05-29 WO PCT/EP2013/061033 patent/WO2013178663A1/en not_active Ceased
- 2013-05-29 EP EP13726744.9A patent/EP2854532B1/en active Active
- 2013-05-29 BR BR112014029123A patent/BR112014029123A2/pt not_active Application Discontinuation
- 2013-05-29 NZ NZ701495A patent/NZ701495A/en not_active IP Right Cessation
- 2013-05-29 JP JP2015514476A patent/JP6130909B2/ja not_active Expired - Fee Related
- 2013-05-29 US US14/404,018 patent/US9398770B2/en active Active
- 2013-05-29 NZ NZ725224A patent/NZ725224A/en not_active IP Right Cessation
- 2013-05-29 ES ES13726744T patent/ES2748624T3/es active Active
- 2013-05-29 CN CN201380029033.2A patent/CN104363758B/zh not_active Expired - Fee Related
- 2013-05-29 IN IN9358DEN2014 patent/IN2014DN09358A/en unknown
- 2013-05-29 MX MX2014014121A patent/MX360058B/es active IP Right Grant
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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
-
2017
- 2017-06-22 IL IL253138A patent/IL253138A0/en unknown
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