TWI691487B - 哌啶酮除草劑 - Google Patents
哌啶酮除草劑 Download PDFInfo
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- TWI691487B TWI691487B TW104121070A TW104121070A TWI691487B TW I691487 B TWI691487 B TW I691487B TW 104121070 A TW104121070 A TW 104121070A TW 104121070 A TW104121070 A TW 104121070A TW I691487 B TWI691487 B TW I691487B
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- Prior art keywords
- compound
- ring
- formula
- phenyl
- oxo
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- 239000004009 herbicide Substances 0.000 title claims description 48
- 230000002363 herbicidal effect Effects 0.000 title claims description 43
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 304
- 239000000203 mixture Substances 0.000 claims abstract description 112
- 238000000034 method Methods 0.000 claims abstract description 58
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims description 139
- 241000196324 Embryophyta Species 0.000 claims description 109
- 125000001424 substituent group Chemical group 0.000 claims description 90
- 239000003112 inhibitor Substances 0.000 claims description 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
- 125000004122 cyclic group Chemical group 0.000 claims description 34
- 239000004480 active ingredient Substances 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 239000003085 diluting agent Substances 0.000 claims description 25
- 239000007788 liquid Substances 0.000 claims description 25
- 239000007787 solid Substances 0.000 claims description 25
- 150000001412 amines Chemical class 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 20
- 239000004094 surface-active agent Substances 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 150000001555 benzenes Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 229930192334 Auxin Natural products 0.000 claims description 10
- 239000002363 auxin Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 102000000452 Acetyl-CoA carboxylase Human genes 0.000 claims description 8
- 108010016219 Acetyl-CoA carboxylase Proteins 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 7
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 7
- 108010001545 phytoene dehydrogenase Proteins 0.000 claims description 7
- 150000004669 very long chain fatty acids Chemical class 0.000 claims description 7
- VYNOULHXXDFBLU-UHFFFAOYSA-N Cumyluron Chemical compound C=1C=CC=CC=1C(C)(C)NC(=O)NCC1=CC=CC=C1Cl VYNOULHXXDFBLU-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- OTSAMNSACVKIOJ-UHFFFAOYSA-N azane;carbamoyl(ethoxy)phosphinic acid Chemical compound [NH4+].CCOP([O-])(=O)C(N)=O OTSAMNSACVKIOJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- ICWUMLXQKFTJMH-UHFFFAOYSA-N Etobenzanid Chemical compound C1=CC(OCOCC)=CC=C1C(=O)NC1=CC=CC(Cl)=C1Cl ICWUMLXQKFTJMH-UHFFFAOYSA-N 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- 108010060806 Photosystem II Protein Complex Proteins 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000002837 carbocyclic group Chemical group 0.000 claims description 5
- 230000008166 cellulose biosynthesis Effects 0.000 claims description 5
- 150000001924 cycloalkanes Chemical class 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 230000008635 plant growth Effects 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
- 108010068327 4-hydroxyphenylpyruvate dioxygenase Proteins 0.000 claims description 4
- 102100028626 4-hydroxyphenylpyruvate dioxygenase Human genes 0.000 claims description 4
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
- 239000005644 Dazomet Substances 0.000 claims description 4
- GXAMYUGOODKVRM-UHFFFAOYSA-N Flurecol Chemical compound C1=CC=C2C(C(=O)O)(O)C3=CC=CC=C3C2=C1 GXAMYUGOODKVRM-UHFFFAOYSA-N 0.000 claims description 4
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 4
- 239000002169 Metam Substances 0.000 claims description 4
- FCOHEOSCARXMMS-UHFFFAOYSA-N Oxaziclomefone Chemical compound C1OC(C)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C1=CC(Cl)=CC(Cl)=C1 FCOHEOSCARXMMS-UHFFFAOYSA-N 0.000 claims description 4
- 239000005643 Pelargonic acid Substances 0.000 claims description 4
- 108010081996 Photosystem I Protein Complex Proteins 0.000 claims description 4
- VGPYEHKOIGNJKV-UHFFFAOYSA-N asulam Chemical compound COC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VGPYEHKOIGNJKV-UHFFFAOYSA-N 0.000 claims description 4
- WZDDLAZXUYIVMU-UHFFFAOYSA-N bromobutide Chemical compound CC(C)(C)C(Br)C(=O)NC(C)(C)C1=CC=CC=C1 WZDDLAZXUYIVMU-UHFFFAOYSA-N 0.000 claims description 4
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 claims description 4
- QMTNOLKHSWIQBE-FGTMMUONSA-N exo-(+)-cinmethylin Chemical compound O([C@H]1[C@]2(C)CC[C@@](O2)(C1)C(C)C)CC1=CC=CC=C1C QMTNOLKHSWIQBE-FGTMMUONSA-N 0.000 claims description 4
- 235000013922 glutamic acid Nutrition 0.000 claims description 4
- 239000004220 glutamic acid Substances 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 3
- 125000006660 (C3-C4) halocycloalkyl group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 3
- LBGPXIPGGRQBJW-UHFFFAOYSA-N Difenzoquat Chemical compound C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 LBGPXIPGGRQBJW-UHFFFAOYSA-N 0.000 claims description 3
- FMINYZXVCTYSNY-UHFFFAOYSA-N Methyldymron Chemical compound C=1C=CC=CC=1N(C)C(=O)NC(C)(C)C1=CC=CC=C1 FMINYZXVCTYSNY-UHFFFAOYSA-N 0.000 claims description 3
- 239000005642 Oleic acid Substances 0.000 claims description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 3
- 108090000992 Transferases Proteins 0.000 claims description 3
- 102000004357 Transferases Human genes 0.000 claims description 3
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims description 3
- 229910052785 arsenic Inorganic materials 0.000 claims description 3
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 3
- HYVVJDQGXFXBRZ-UHFFFAOYSA-N metam Chemical compound CNC(S)=S HYVVJDQGXFXBRZ-UHFFFAOYSA-N 0.000 claims description 3
- 230000000394 mitotic effect Effects 0.000 claims description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 2
- 241000209761 Avena Species 0.000 claims description 2
- 235000007319 Avena orientalis Nutrition 0.000 claims description 2
- 229940106987 Elongase inhibitor Drugs 0.000 claims description 2
- 108090000854 Oxidoreductases Proteins 0.000 claims description 2
- 102000004316 Oxidoreductases Human genes 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 6
- 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
- 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
- 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
- GVACZEXJWONLFR-UHFFFAOYSA-N C1CN(C(=O)C(C1C2=CC(=CC=C2)C(F)F)C(=O)O)C3=C(C(=CC=C3)F)F Chemical compound C1CN(C(=O)C(C1C2=CC(=CC=C2)C(F)F)C(=O)O)C3=C(C(=CC=C3)F)F GVACZEXJWONLFR-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 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- 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 description 41
- 238000006243 chemical reaction Methods 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 25
- 238000009472 formulation Methods 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 125000000623 heterocyclic group Chemical group 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 23
- 239000000243 solution Substances 0.000 description 21
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- 238000012360 testing method Methods 0.000 description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 19
- 239000002585 base Substances 0.000 description 19
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 19
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- 239000011734 sodium Substances 0.000 description 19
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 16
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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- 125000004429 atom Chemical group 0.000 description 14
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- 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 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000000753 cycloalkyl group Chemical group 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 238000006467 substitution reaction Methods 0.000 description 12
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- 125000003545 alkoxy group Chemical group 0.000 description 11
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- 239000000194 fatty acid Substances 0.000 description 11
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- 125000001188 haloalkyl group Chemical group 0.000 description 10
- 159000000000 sodium salts Chemical class 0.000 description 10
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- 239000002253 acid Substances 0.000 description 9
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- 239000002689 soil Substances 0.000 description 9
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 8
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- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 6
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- 239000011975 tartaric acid Substances 0.000 description 1
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
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- 230000009974 thixotropic effect Effects 0.000 description 1
- 210000002377 thylakoid Anatomy 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- 125000005389 trialkylsiloxy group Chemical group 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
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- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- AZHZOGYUMMIAOF-UHFFFAOYSA-N trifludimoxazin Chemical compound O=C1N(C)C(=S)N(C)C(=O)N1C(C(=C1)F)=CC2=C1OC(F)(F)C(=O)N2CC#C AZHZOGYUMMIAOF-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D417/02—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 two hetero rings
- C07D417/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| US11589583B2 (en) | 2013-12-03 | 2023-02-28 | Fmc Corporation | Pyrrolidinones herbicides |
| EP3230264B1 (en) | 2014-12-08 | 2019-09-11 | FMC Corporation | 3-oxo-3-(arylamino)propanoates, a process for their preparation, and their use in preparing pyrrolidinones |
| EP3280709B1 (en) * | 2015-04-10 | 2021-05-26 | FMC Corporation | Substituted cyclic amides as herbicides |
| CN107531658B (zh) * | 2015-04-27 | 2021-07-27 | Fmc公司 | 作为除草剂的丁内酯 |
| PL3294743T3 (pl) | 2015-05-12 | 2020-03-31 | Fmc Corporation | Podstawione arylem związki bicykliczne jako środki chwastobójcze |
| EP3303287B1 (en) | 2015-05-29 | 2020-12-16 | FMC Corporation | Substituted cyclic amides as herbicides |
| US10654804B2 (en) | 2015-06-02 | 2020-05-19 | Fmc Corporation | Substituted cyclic amides and their use as herbicides |
| AU2016303209B2 (en) | 2015-07-31 | 2021-04-01 | Fmc Corporation | Cyclic N-carboxamide compounds useful as herbicides |
| GB201617062D0 (en) * | 2016-10-07 | 2016-11-23 | Syngenta Participations Ag | Herbicidal mixtures |
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| EP3558962B1 (en) * | 2016-12-21 | 2023-07-12 | FMC Corporation | Nitrone herbicides |
| WO2018167347A2 (es) * | 2017-03-14 | 2018-09-20 | PlantResponse Biotech, S.L. | Métodos y composiciones para mejorar la salud de plantas y/o rendimiento de plantas |
| BR112019019551A2 (pt) | 2017-03-21 | 2020-04-22 | Fmc Corp | mistura, e, método para controlar o crescimento de vegetação indesejada |
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| WO2018178010A1 (de) * | 2017-03-30 | 2018-10-04 | Bayer Aktiengesellschaft | N-cyclopropyl-2-oxo-4-phenyl-piperidin-3-carboxamid-derivate und verwandte verbindungen als herbizide pflanzenschutzmittel |
| WO2018177837A1 (de) | 2017-03-30 | 2018-10-04 | Bayer Aktiengesellschaft | 4-cyclopentyl- und 4-cyclopropyl-2-oxopyrrolidin-3-carboxami d-derivate und verwandte verbindungen als herbizide pflanzenschutzmittel |
| WO2018177836A1 (de) | 2017-03-30 | 2018-10-04 | Bayer Aktiengesellschaft | N-cyclopropyl-2-oxopyrrolidin-3-carboxamid-derivate und verwandte verbindungen als herbizide pflanzenschutzmittel |
| WO2018178012A1 (de) * | 2017-03-30 | 2018-10-04 | Bayer Aktiengesellschaft | N-benzyl-2-oxo-4-phenyl-piperidin-3-carboxamid-derivate und verwandte verbindungen als herbizide pflanzenschutzmittel |
| 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 |
| AR111967A1 (es) | 2017-05-30 | 2019-09-04 | Fmc Corp | Amidas herbicidas |
| AR111839A1 (es) * | 2017-05-30 | 2019-08-21 | Fmc Corp | Lactamas 3-sustituidas herbicidas |
| CN110934149B (zh) * | 2018-09-21 | 2021-03-02 | 华中师范大学 | 含氯酰草膦除草剂的微乳剂制剂及其制备方法和应用 |
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| EP2336104A1 (en) * | 2008-09-02 | 2011-06-22 | Nissan Chemical Industries, Ltd. | Ortho-substituted haloalkylsulfonanilide derivative and herbicide |
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| GB201321743D0 (en) | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
| RU2555370C1 (ru) | 2014-02-12 | 2015-07-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Самарский государственный технический университет" | Способ энантиоселективного синтеза диэтил[3-метил-(1s)-(нитрометил)бутил]малоната формулы i |
| EP3230264B1 (en) | 2014-12-08 | 2019-09-11 | FMC Corporation | 3-oxo-3-(arylamino)propanoates, a process for their preparation, and their use in preparing pyrrolidinones |
| EP3280709B1 (en) | 2015-04-10 | 2021-05-26 | FMC Corporation | Substituted cyclic amides as herbicides |
| CN107531658B (zh) | 2015-04-27 | 2021-07-27 | Fmc公司 | 作为除草剂的丁内酯 |
| EP3303287B1 (en) | 2015-05-29 | 2020-12-16 | FMC Corporation | Substituted cyclic amides as herbicides |
| US10654804B2 (en) | 2015-06-02 | 2020-05-19 | Fmc Corporation | Substituted cyclic amides and their use as herbicides |
| AU2016303209B2 (en) | 2015-07-31 | 2021-04-01 | Fmc Corporation | Cyclic N-carboxamide compounds useful as herbicides |
-
2015
- 2015-06-30 EP EP15734050.6A patent/EP3164386B1/en not_active Not-in-force
- 2015-06-30 BR BR112016030930-8A patent/BR112016030930B1/pt not_active IP Right Cessation
- 2015-06-30 EA EA201790125A patent/EA032798B1/ru unknown
- 2015-06-30 KR KR1020177002688A patent/KR102479858B1/ko active Active
- 2015-06-30 PE PE2017000005A patent/PE20170444A1/es unknown
- 2015-06-30 CA CA2953548A patent/CA2953548C/en active Active
- 2015-06-30 JP JP2017521023A patent/JP2017522374A/ja active Pending
- 2015-06-30 MX MX2016017251A patent/MX389921B/es unknown
- 2015-06-30 TW TW104121070A patent/TWI691487B/zh active
- 2015-06-30 US US15/323,528 patent/US9944602B2/en active Active
- 2015-06-30 CN CN201580046635.8A patent/CN106715412B/zh not_active Expired - Fee Related
- 2015-06-30 MY MYPI2016704737A patent/MY178627A/en unknown
- 2015-06-30 UA UAA201700856A patent/UA125012C2/uk unknown
- 2015-06-30 AU AU2015284280A patent/AU2015284280C1/en not_active Ceased
- 2015-06-30 SG SG11201610720VA patent/SG11201610720VA/en unknown
- 2015-06-30 WO PCT/US2015/038473 patent/WO2016003997A1/en not_active Ceased
- 2015-07-02 UY UY0001036201A patent/UY36201A/es not_active Application Discontinuation
- 2015-07-02 AR ARP150102132A patent/AR101102A1/es active IP Right Grant
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2016
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2020
- 2020-05-28 JP JP2020093072A patent/JP7088984B2/ja active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2336104A1 (en) * | 2008-09-02 | 2011-06-22 | Nissan Chemical Industries, Ltd. | Ortho-substituted haloalkylsulfonanilide derivative and herbicide |
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