JP2017522374A5 - - Google Patents

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Publication number: JP2017522374A5
Authority: JP; Japan
Prior art keywords: phenyl; alkyl; cycloalkyl; piperidinecarboxamide; oxo
Prior art date: 2015-06-30
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.): Pending

Application number

JP2017521023A

Other languages

English (en)

Japanese (ja)

Other versions

JP2017522374A (ja

Filing date

2015-06-30

Publication date

2019-10-03

2015-06-30 Application filed filed Critical

2015-06-30 Priority claimed from PCT/US2015/038473 external-priority patent/WO2016003997A1/en

2017-08-10 Publication of JP2017522374A publication Critical patent/JP2017522374A/ja

2019-10-03 Publication of JP2017522374A5 publication Critical patent/JP2017522374A5/ja

Status Pending legal-status Critical Current

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-1 hydroxy, amino Chemical group 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
125000003302 alkenyloxy group Chemical group 0.000 claims description 4
125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 4
125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 4
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000005133 alkynyloxy group Chemical group 0.000 claims description 4
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 4
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 3
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 3
125000004663 dialkyl amino group Chemical group 0.000 claims description 3
125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 3
125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 2
125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 26
125000001424 substituent group Chemical group 0.000 claims 5
150000001875 compounds Chemical class 0.000 claims 4
125000004433 nitrogen atom Chemical group N* 0.000 claims 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims 3
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 3
125000004448 alkyl carbonyl group Chemical group 0.000 claims 3
125000004692 haloalkylcarbonyl group Chemical group 0.000 claims 3
125000004665 trialkylsilyl group Chemical group 0.000 claims 3
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 2
125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims 2
125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 2
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims 2
125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
125000006815 (C4-C10) cycloalkylaminocarbonyl group Chemical group 0.000 claims 2
125000006781 (C4-C10) cycloalkylcarbonyl group Chemical group 0.000 claims 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 2
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 2
125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims 2
125000002619 bicyclic group Chemical group 0.000 claims 2
150000001721 carbon Chemical group 0.000 claims 2
125000004432 carbon atom Chemical group C* 0.000 claims 2
125000004093 cyano group Chemical group *C#N 0.000 claims 2
125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims 2
125000005366 cycloalkylthio group Chemical group 0.000 claims 2
239000003085 diluting agent Substances 0.000 claims 2
125000004994 halo alkoxy alkyl group Chemical group 0.000 claims 2
125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims 2
229910052736 halogen Inorganic materials 0.000 claims 2
150000002367 halogens Chemical class 0.000 claims 2
125000005842 heteroatom Chemical group 0.000 claims 2
125000004434 sulfur atom Chemical group 0.000 claims 2
SXUBVSXXRKXIQW-IUODEOHRSA-N (3R,4S)-4-(3-chlorophenyl)-N-(2,3-difluorophenyl)-2-oxopiperidine-3-carboxamide Chemical compound ClC=1C=C(C=CC=1)[C@@H]1[C@H](C(NCC1)=O)C(=O)NC1=C(C(=CC=C1)F)F SXUBVSXXRKXIQW-IUODEOHRSA-N 0.000 claims 1
KSFKMZVIVWNXME-IUODEOHRSA-N (3R,4S)-N-(2,3-difluorophenyl)-2-oxo-4-[3-(trifluoromethyl)phenyl]piperidine-3-carboxamide Chemical compound FC1=C(C=CC=C1F)NC(=O)[C@H]1C(NCC[C@@H]1C1=CC(=CC=C1)C(F)(F)F)=O KSFKMZVIVWNXME-IUODEOHRSA-N 0.000 claims 1
GHSUTCLEVLBVEL-IUODEOHRSA-N (3R,4S)-N-(2,3-difluorophenyl)-2-oxo-4-[4-(trifluoromethyl)phenyl]piperidine-3-carboxamide Chemical compound FC1=C(C=CC=C1F)NC(=O)[C@H]1C(NCC[C@@H]1C1=CC=C(C=C1)C(F)(F)F)=O GHSUTCLEVLBVEL-IUODEOHRSA-N 0.000 claims 1
GERCBSOTQXAVBS-IUODEOHRSA-N (3R,4S)-N-(3-chloro-2-fluorophenyl)-2-oxo-4-[3-(trifluoromethyl)phenyl]piperidine-3-carboxamide Chemical compound ClC=1C(=C(C=CC=1)NC(=O)[C@H]1C(NCC[C@@H]1C1=CC(=CC=C1)C(F)(F)F)=O)F GERCBSOTQXAVBS-IUODEOHRSA-N 0.000 claims 1
KNJJANUGPUMOGP-CJNGLKHVSA-N (3S,4S)-N-(2,3-difluorophenyl)-4-(4-fluorophenyl)-1-methyl-2-oxopiperidine-3-carboxamide Chemical compound FC1=C(C=CC=C1F)NC(=O)[C@H]1C(N(CC[C@@H]1C1=CC=C(C=C1)F)C)=O KNJJANUGPUMOGP-CJNGLKHVSA-N 0.000 claims 1
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 1
LTRLUOORVJPZDA-UHFFFAOYSA-N 2-oxo-4-[3-(trifluoromethyl)phenyl]-N-(2,3,4-trifluorophenyl)piperidine-3-carboxamide Chemical compound O=C1NCCC(C1C(=O)NC1=C(C(=C(C=C1)F)F)F)C1=CC(=CC=C1)C(F)(F)F LTRLUOORVJPZDA-UHFFFAOYSA-N 0.000 claims 1
GSTKTRLJYUFJFV-UHFFFAOYSA-N 2-oxo-N-[2-(trifluoromethyl)phenyl]-4-[3-(trifluoromethyl)phenyl]piperidine-3-carboxamide Chemical compound O=C1NCCC(C1C(=O)NC1=C(C=CC=C1)C(F)(F)F)C1=CC(=CC=C1)C(F)(F)F GSTKTRLJYUFJFV-UHFFFAOYSA-N 0.000 claims 1
SXUBVSXXRKXIQW-UHFFFAOYSA-N 4-(3-chlorophenyl)-N-(2,3-difluorophenyl)-2-oxopiperidine-3-carboxamide Chemical compound ClC=1C=C(C=CC=1)C1C(C(NCC1)=O)C(=O)NC1=C(C(=CC=C1)F)F SXUBVSXXRKXIQW-UHFFFAOYSA-N 0.000 claims 1
JXKXEUHAXJIBBI-UHFFFAOYSA-N 4-[3-(difluoromethyl)phenyl]-N-(2,3-difluorophenyl)-2-oxopiperidine-3-carboxamide Chemical compound FC(C=1C=C(C=CC=1)C1C(C(NCC1)=O)C(=O)NC1=C(C(=CC=C1)F)F)F JXKXEUHAXJIBBI-UHFFFAOYSA-N 0.000 claims 1
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
KSFKMZVIVWNXME-UHFFFAOYSA-N N-(2,3-difluorophenyl)-2-oxo-4-[3-(trifluoromethyl)phenyl]piperidine-3-carboxamide Chemical compound FC1=C(C=CC=C1F)NC(=O)C1C(NCCC1C1=CC(=CC=C1)C(F)(F)F)=O KSFKMZVIVWNXME-UHFFFAOYSA-N 0.000 claims 1
GHSUTCLEVLBVEL-UHFFFAOYSA-N N-(2,3-difluorophenyl)-2-oxo-4-[4-(trifluoromethyl)phenyl]piperidine-3-carboxamide Chemical compound FC1=C(C=CC=C1F)NC(=O)C1C(NCCC1C1=CC=C(C=C1)C(F)(F)F)=O GHSUTCLEVLBVEL-UHFFFAOYSA-N 0.000 claims 1
150000001204 N-oxides Chemical class 0.000 claims 1
125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims 1
125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims 1
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
125000002837 carbocyclic group Chemical group 0.000 claims 1
230000006315 carbonylation Effects 0.000 claims 1
238000005810 carbonylation reaction Methods 0.000 claims 1
125000005159 cyanoalkoxy group Chemical group 0.000 claims 1
125000004966 cyanoalkyl group Chemical group 0.000 claims 1
125000005357 cycloalkylalkynyl group Chemical group 0.000 claims 1
125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims 1
125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims 1
125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims 1
125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 claims 1
125000000262 haloalkenyl group Chemical group 0.000 claims 1
125000005291 haloalkenyloxy group Chemical group 0.000 claims 1
125000004438 haloalkoxy group Chemical group 0.000 claims 1
125000001188 haloalkyl group Chemical group 0.000 claims 1
125000005203 haloalkylcarbonyloxy group Chemical group 0.000 claims 1
125000004440 haloalkylsulfinyl group Chemical group 0.000 claims 1
125000004441 haloalkylsulfonyl group Chemical group 0.000 claims 1
125000004995 haloalkylthio group Chemical group 0.000 claims 1
125000000232 haloalkynyl group Chemical group 0.000 claims 1
125000005292 haloalkynyloxy group Chemical group 0.000 claims 1
125000005347 halocycloalkyl group Chemical group 0.000 claims 1
125000004461 halocycloalkylalkyl group Chemical group 0.000 claims 1
230000002363 herbicidal effect Effects 0.000 claims 1
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
239000007788 liquid Substances 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
125000004971 nitroalkyl group Chemical group 0.000 claims 1
GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
125000006513 pyridinyl methyl group Chemical group 0.000 claims 1
125000004076 pyridyl group Chemical group 0.000 claims 1
150000003839 salts Chemical class 0.000 claims 1
239000007787 solid Substances 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 claims 1
239000004094 surface-active agent Substances 0.000 claims 1
125000001544 thienyl group Chemical group 0.000 claims 1
238000006467 substitution reaction Methods 0.000 description 8
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 4
101150065749 Churc1 gene Proteins 0.000 description 4
102100038239 Protein Churchill Human genes 0.000 description 4
125000004430 oxygen atom Chemical group O* 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
SSUFDOMYCBCHML-UHFFFAOYSA-N CCCCC[S](=O)=O Chemical class CCCCC[S](=O)=O SSUFDOMYCBCHML-UHFFFAOYSA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1

JP2017521023A 2014-07-02 2015-06-30 ピペリジノン除草剤 Pending JP2017522374A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US201462020140P	2014-07-02	2014-07-02
US62/020,140		2014-07-02
PCT/US2015/038473 WO2016003997A1 (en)	2014-07-02	2015-06-30	Piperidinone herbicides

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2020093072A Division JP7088984B2 (ja)	2014-07-02	2020-05-28	ピペリジノン除草剤

Publications (2)

Publication Number	Publication Date
JP2017522374A JP2017522374A (ja)	2017-08-10
JP2017522374A5 true JP2017522374A5 (2)	2019-10-03

Family

ID=53511066

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
JP2017521023A Pending JP2017522374A (ja)	2014-07-02	2015-06-30	ピペリジノン除草剤
JP2020093072A Expired - Fee Related JP7088984B2 (ja)	2014-07-02	2020-05-28	ピペリジノン除草剤

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
JP2020093072A Expired - Fee Related JP7088984B2 (ja)	2014-07-02	2020-05-28	ピペリジノン除草剤

Country Status (21)

Country	Link
US (1)	US9944602B2 (2)
EP (1)	EP3164386B1 (2)
JP (2)	JP2017522374A (2)
KR (1)	KR102479858B1 (2)
CN (1)	CN106715412B (2)
AR (1)	AR101102A1 (2)
AU (1)	AU2015284280C1 (2)
BR (1)	BR112016030930B1 (2)
CA (1)	CA2953548C (2)
CL (1)	CL2016003416A1 (2)
EA (1)	EA032798B1 (2)
IL (1)	IL249699B (2)
MX (1)	MX389921B (2)
MY (1)	MY178627A (2)
PE (1)	PE20170444A1 (2)
PH (1)	PH12016502594A1 (2)
SG (1)	SG11201610720VA (2)
TW (1)	TWI691487B (2)
UA (1)	UA125012C2 (2)
UY (1)	UY36201A (2)
WO (1)	WO2016003997A1 (2)

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WO2018184891A1 (de) *	2017-04-05	2018-10-11	Bayer Aktiengesellschaft	4-substituierte n-amino und n-hydroxy 2-oxo-piperidin-3-carboxamid-derivate, deren salze und ihre verwendung als herbizide wirkstoffe
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