WO2018019767A1 - Composés herbicides de pyridine - Google Patents
Composés herbicides de pyridine Download PDFInfo
- Publication number
- WO2018019767A1 WO2018019767A1 PCT/EP2017/068640 EP2017068640W WO2018019767A1 WO 2018019767 A1 WO2018019767 A1 WO 2018019767A1 EP 2017068640 W EP2017068640 W EP 2017068640W WO 2018019767 A1 WO2018019767 A1 WO 2018019767A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- haloalkyl
- cycloalkyl
- alkoxy
- methyl
- Prior art date
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- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 155
- 150000003222 pyridines Chemical class 0.000 title claims abstract description 144
- 239000000203 mixture Substances 0.000 claims abstract description 430
- 239000004009 herbicide Substances 0.000 claims abstract description 215
- 150000003839 salts Chemical class 0.000 claims abstract description 99
- 238000000034 method Methods 0.000 claims abstract description 25
- -1 Ci-C6-alkoxy Chemical group 0.000 claims description 686
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 196
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 145
- 239000003112 inhibitor Substances 0.000 claims description 93
- 150000002148 esters Chemical class 0.000 claims description 87
- 229910052736 halogen Inorganic materials 0.000 claims description 60
- 150000002367 halogens Chemical class 0.000 claims description 48
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 45
- 229910052717 sulfur Inorganic materials 0.000 claims description 43
- 229910052760 oxygen Inorganic materials 0.000 claims description 40
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 230000015572 biosynthetic process Effects 0.000 claims description 23
- 125000004122 cyclic group Chemical group 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000001931 aliphatic group Chemical group 0.000 claims description 13
- 125000002619 bicyclic group Chemical group 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 239000004094 surface-active agent Substances 0.000 claims description 13
- 125000002015 acyclic group Chemical group 0.000 claims description 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 10
- 150000004669 very long chain fatty acids Chemical class 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 9
- 108010000700 Acetolactate synthase Proteins 0.000 claims description 8
- 229930192334 Auxin Natural products 0.000 claims description 8
- PMAAYIYCDXGUAP-UHFFFAOYSA-N Indanofan Chemical compound O=C1C2=CC=CC=C2C(=O)C1(CC)CC1(C=2C=C(Cl)C=CC=2)CO1 PMAAYIYCDXGUAP-UHFFFAOYSA-N 0.000 claims description 8
- 108020001991 Protoporphyrinogen Oxidase Proteins 0.000 claims description 8
- 239000002363 auxin Substances 0.000 claims description 8
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 8
- 150000002632 lipids Chemical class 0.000 claims description 8
- IUFUITYPUYMIHI-UHFFFAOYSA-N N-[1-(3,5-dimethylphenoxy)propan-2-yl]-6-(2-fluoropropan-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N)=NC(C(C)(C)F)=NC=1NC(C)COC1=CC(C)=CC(C)=C1 IUFUITYPUYMIHI-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- 102000005135 Protoporphyrinogen oxidase Human genes 0.000 claims description 7
- 230000008166 cellulose biosynthesis Effects 0.000 claims description 7
- 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 7
- YFONKFDEZLYQDH-BOURZNODSA-N indaziflam Chemical compound CC(F)C1=NC(N)=NC(N[C@H]2C3=CC(C)=CC=C3C[C@@H]2C)=N1 YFONKFDEZLYQDH-BOURZNODSA-N 0.000 claims description 7
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims description 7
- 230000029553 photosynthesis Effects 0.000 claims description 7
- 238000010672 photosynthesis Methods 0.000 claims description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- 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
- 230000011278 mitosis Effects 0.000 claims description 6
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 6
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 6
- OPEJGICLTMWFNQ-UHFFFAOYSA-N 5-[(2,6-difluorophenyl)methoxymethyl]-5-methyl-3-(3-methylthiophen-2-yl)-4h-1,2-oxazole Chemical compound C1=CSC(C=2CC(C)(COCC=3C(=CC=CC=3F)F)ON=2)=C1C OPEJGICLTMWFNQ-UHFFFAOYSA-N 0.000 claims description 5
- GZJVZGUUTYWVTP-UHFFFAOYSA-N 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-1h-pyridazin-4-one Chemical compound N=1N=C(Cl)C=C(O)C=1OC=1C(C)=CC=CC=1C1CC1 GZJVZGUUTYWVTP-UHFFFAOYSA-N 0.000 claims description 5
- NDUPDOJHUQKPAG-UHFFFAOYSA-N Dalapon Chemical compound CC(Cl)(Cl)C(O)=O NDUPDOJHUQKPAG-UHFFFAOYSA-N 0.000 claims description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- XQEMNBNCQVQXMO-UHFFFAOYSA-M 1,2-dimethyl-3,5-diphenylpyrazol-1-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 XQEMNBNCQVQXMO-UHFFFAOYSA-M 0.000 claims description 4
- 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 4
- 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 4
- YQVMVCCFZCMYQB-UHFFFAOYSA-N Flamprop Chemical compound C=1C=C(F)C(Cl)=CC=1N(C(C)C(O)=O)C(=O)C1=CC=CC=C1 YQVMVCCFZCMYQB-UHFFFAOYSA-N 0.000 claims description 4
- 239000002169 Metam Substances 0.000 claims description 4
- IBZHOAONZVJLOB-UHFFFAOYSA-N Tridiphane Chemical compound ClC1=CC(Cl)=CC(C2(CC(Cl)(Cl)Cl)OC2)=C1 IBZHOAONZVJLOB-UHFFFAOYSA-N 0.000 claims description 4
- 208000014347 autosomal dominant hyaline body myopathy Diseases 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
- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 claims description 4
- 102000005396 glutamine synthetase Human genes 0.000 claims description 4
- 108020002326 glutamine synthetase Proteins 0.000 claims description 4
- HYVVJDQGXFXBRZ-UHFFFAOYSA-N metam Chemical compound CNC(S)=S HYVVJDQGXFXBRZ-UHFFFAOYSA-N 0.000 claims description 4
- RBNIGDFIUWJJEV-LLVKDONJSA-N methyl (2r)-2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical group C=1C=C(F)C(Cl)=CC=1N([C@H](C)C(=O)OC)C(=O)C1=CC=CC=C1 RBNIGDFIUWJJEV-LLVKDONJSA-N 0.000 claims description 4
- RBNIGDFIUWJJEV-UHFFFAOYSA-N methyl 2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical group C=1C=C(F)C(Cl)=CC=1N(C(C)C(=O)OC)C(=O)C1=CC=CC=C1 RBNIGDFIUWJJEV-UHFFFAOYSA-N 0.000 claims description 4
- 229940102396 methyl bromide Drugs 0.000 claims description 4
- JITOKQVGRJSHHA-UHFFFAOYSA-M monosodium methyl arsenate Chemical compound [Na+].C[As](O)([O-])=O JITOKQVGRJSHHA-UHFFFAOYSA-M 0.000 claims description 4
- IKVXBIIHQGXQRQ-CYBMUJFWSA-N propan-2-yl (2r)-2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical group C=1C=C(F)C(Cl)=CC=1N([C@H](C)C(=O)OC(C)C)C(=O)C1=CC=CC=C1 IKVXBIIHQGXQRQ-CYBMUJFWSA-N 0.000 claims description 4
- IKVXBIIHQGXQRQ-UHFFFAOYSA-N propan-2-yl 2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical group C=1C=C(F)C(Cl)=CC=1N(C(C)C(=O)OC(C)C)C(=O)C1=CC=CC=C1 IKVXBIIHQGXQRQ-UHFFFAOYSA-N 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
- GXEKYRXVRROBEV-FBXFSONDSA-N (1r,2s,3r,4s)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid Chemical compound C1C[C@@H]2[C@@H](C(O)=O)[C@@H](C(=O)O)[C@H]1O2 GXEKYRXVRROBEV-FBXFSONDSA-N 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
- SVOAUHHKPGKPQK-UHFFFAOYSA-N 2-chloro-9-hydroxyfluorene-9-carboxylic acid Chemical compound C1=C(Cl)C=C2C(C(=O)O)(O)C3=CC=CC=C3C2=C1 SVOAUHHKPGKPQK-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
- WBFYVDCHGVNRBH-UHFFFAOYSA-N 7,8-dihydropteroic acid Chemical compound N=1C=2C(=O)NC(N)=NC=2NCC=1CNC1=CC=C(C(O)=O)C=C1 WBFYVDCHGVNRBH-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
- 239000005644 Dazomet Substances 0.000 claims description 3
- PHVNLLCAQHGNKU-UHFFFAOYSA-N Dimethipin Chemical compound CC1=C(C)S(=O)(=O)CCS1(=O)=O PHVNLLCAQHGNKU-UHFFFAOYSA-N 0.000 claims description 3
- ICWUMLXQKFTJMH-UHFFFAOYSA-N Etobenzanid Chemical compound C1=CC(OCOCC)=CC=C1C(=O)NC1=CC=CC(Cl)=C1Cl ICWUMLXQKFTJMH-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- VEVZCONIUDBCDC-UHFFFAOYSA-N Flurprimidol Chemical compound C=1N=CN=CC=1C(O)(C(C)C)C1=CC=C(OC(F)(F)F)C=C1 VEVZCONIUDBCDC-UHFFFAOYSA-N 0.000 claims description 3
- 239000005983 Maleic hydrazide Substances 0.000 claims description 3
- BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 claims description 3
- OKIBNKKYNPBDRS-UHFFFAOYSA-N Mefluidide Chemical compound CC(=O)NC1=CC(NS(=O)(=O)C(F)(F)F)=C(C)C=C1C OKIBNKKYNPBDRS-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
- 239000005643 Pelargonic acid Substances 0.000 claims description 3
- OBLNWSCLAYSJJR-UHFFFAOYSA-N Quinoclamin Chemical compound C1=CC=C2C(=O)C(N)=C(Cl)C(=O)C2=C1 OBLNWSCLAYSJJR-UHFFFAOYSA-N 0.000 claims description 3
- 239000002167 Quinoclamine Substances 0.000 claims description 3
- PSGPXWYGJGGEEG-UHFFFAOYSA-N butyl 9-hydroxyfluorene-9-carboxylate Chemical group C1=CC=C2C(C(=O)OCCCC)(O)C3=CC=CC=C3C2=C1 PSGPXWYGJGGEEG-UHFFFAOYSA-N 0.000 claims description 3
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-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
- LINPVWIEWJTEEJ-UHFFFAOYSA-N methyl 2-chloro-9-hydroxyfluorene-9-carboxylate Chemical group C1=C(Cl)C=C2C(C(=O)OC)(O)C3=CC=CC=C3C2=C1 LINPVWIEWJTEEJ-UHFFFAOYSA-N 0.000 claims description 3
- PBTHJVDBCFJQGG-UHFFFAOYSA-N methyl azide Chemical compound CN=[N+]=[N-] PBTHJVDBCFJQGG-UHFFFAOYSA-N 0.000 claims description 3
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- QYOJSKGCWNAKGW-HCWXCVPCSA-N shikimate-3-phosphate Chemical compound O[C@H]1CC(C(O)=O)=C[C@H](OP(O)(O)=O)[C@@H]1O QYOJSKGCWNAKGW-HCWXCVPCSA-N 0.000 claims description 3
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- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 3
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- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 387
- 235000013350 formula milk Nutrition 0.000 description 315
- 230000000875 corresponding effect Effects 0.000 description 126
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 92
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 57
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- WRBJKRRJBCSNLE-UHFFFAOYSA-M potassium;4-(2,4-dichlorophenoxy)butanoate Chemical compound [K+].[O-]C(=O)CCCOC1=CC=C(Cl)C=C1Cl WRBJKRRJBCSNLE-UHFFFAOYSA-M 0.000 description 1
- ZRHANBBTXQZFSP-UHFFFAOYSA-M potassium;4-amino-3,5,6-trichloropyridine-2-carboxylate Chemical compound [K+].NC1=C(Cl)C(Cl)=NC(C([O-])=O)=C1Cl ZRHANBBTXQZFSP-UHFFFAOYSA-M 0.000 description 1
- XUYNZTABHAFFAO-UHFFFAOYSA-M potassium;4-amino-3,6-dichloropyridine-2-carboxylate Chemical compound [K+].NC1=CC(Cl)=NC(C([O-])=O)=C1Cl XUYNZTABHAFFAO-UHFFFAOYSA-M 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- ISEUFVQQFVOBCY-UHFFFAOYSA-N prometon Chemical compound COC1=NC(NC(C)C)=NC(NC(C)C)=N1 ISEUFVQQFVOBCY-UHFFFAOYSA-N 0.000 description 1
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- WHOKDONDRZNCBC-UHFFFAOYSA-N propan-2-yl 2-(2,4-dichlorophenoxy)acetate Chemical group CC(C)OC(=O)COC1=CC=C(Cl)C=C1Cl WHOKDONDRZNCBC-UHFFFAOYSA-N 0.000 description 1
- BOEYMHRHUPNCAQ-UHFFFAOYSA-N propan-2-yl 2-(4-chloro-2-methylphenoxy)acetate Chemical group CC(C)OC(=O)COC1=CC=C(Cl)C=C1C BOEYMHRHUPNCAQ-UHFFFAOYSA-N 0.000 description 1
- FKLQIONHGSFYJY-UHFFFAOYSA-N propan-2-yl 5-[4-bromo-1-methyl-5-(trifluoromethyl)pyrazol-3-yl]-2-chloro-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(C=2C(=C(N(C)N=2)C(F)(F)F)Br)=C1F FKLQIONHGSFYJY-UHFFFAOYSA-N 0.000 description 1
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 1
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- URELEWKDONECLX-UHFFFAOYSA-N propyl 2-(2,4-dichlorophenoxy)acetate Chemical group CCCOC(=O)COC1=CC=C(Cl)C=C1Cl URELEWKDONECLX-UHFFFAOYSA-N 0.000 description 1
- ZHYPDEKPSXOZKN-UHFFFAOYSA-N propyl 4-[[2-(4,6-dimethoxypyrimidin-2-yl)oxyphenyl]methylamino]benzoate Chemical compound C1=CC(C(=O)OCCC)=CC=C1NCC1=CC=CC=C1OC1=NC(OC)=CC(OC)=N1 ZHYPDEKPSXOZKN-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- PHNUZKMIPFFYSO-UHFFFAOYSA-N propyzamide Chemical compound C#CC(C)(C)NC(=O)C1=CC(Cl)=CC(Cl)=C1 PHNUZKMIPFFYSO-UHFFFAOYSA-N 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 description 1
- DVLHGMFTRAFHPR-UHFFFAOYSA-N pyrazole-1-carboxamide Chemical compound NC(=O)N1C=CC=N1 DVLHGMFTRAFHPR-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- FKERUJTUOYLBKB-UHFFFAOYSA-N pyrazoxyfen Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=CC=C1 FKERUJTUOYLBKB-UHFFFAOYSA-N 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 150000008512 pyrimidinediones Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- DEIKMOQTJBGGAX-DJKKODMXSA-N pyriminobac Chemical compound CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(O)=O DEIKMOQTJBGGAX-DJKKODMXSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- BBKDWPHJZANJGB-UHFFFAOYSA-N quizalofop-p-tefuryl Chemical group C=1C=C(OC=2N=C3C=CC(Cl)=CC3=NC=2)C=CC=1OC(C)C(=O)OCC1CCCO1 BBKDWPHJZANJGB-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- DPMABEYFRYKAHD-UHFFFAOYSA-M sodium;2,3,6-trichlorobenzoate Chemical compound [Na+].[O-]C(=O)C1=C(Cl)C=CC(Cl)=C1Cl DPMABEYFRYKAHD-UHFFFAOYSA-M 0.000 description 1
- RFOHRSIAXQACDB-UHFFFAOYSA-M sodium;2-(2,4-dichlorophenoxy)acetate Chemical compound [Na+].[O-]C(=O)COC1=CC=C(Cl)C=C1Cl RFOHRSIAXQACDB-UHFFFAOYSA-M 0.000 description 1
- XWAFIZUTHLRWBE-UHFFFAOYSA-M sodium;2-(2,4-dichlorophenoxy)propanoate Chemical compound [Na+].[O-]C(=O)C(C)OC1=CC=C(Cl)C=C1Cl XWAFIZUTHLRWBE-UHFFFAOYSA-M 0.000 description 1
- STAPBGVGYWCRTF-UHFFFAOYSA-M sodium;2-(4-chloro-2-methylphenoxy)acetate Chemical compound [Na+].CC1=CC(Cl)=CC=C1OCC([O-])=O STAPBGVGYWCRTF-UHFFFAOYSA-M 0.000 description 1
- DHJHUXNTNSRSEX-UHFFFAOYSA-M sodium;2-(4-chloro-2-methylphenoxy)propanoate Chemical compound [Na+].[O-]C(=O)C(C)OC1=CC=C(Cl)C=C1C DHJHUXNTNSRSEX-UHFFFAOYSA-M 0.000 description 1
- YWICANUUQPYHOW-UHFFFAOYSA-M sodium;2-(phosphonomethylamino)acetate Chemical compound [Na+].OP(O)(=O)CNCC([O-])=O YWICANUUQPYHOW-UHFFFAOYSA-M 0.000 description 1
- WMWBBXKLYSGKDY-UHFFFAOYSA-M sodium;3-amino-2,5-dichlorobenzoate Chemical compound [Na+].NC1=CC(Cl)=CC(C([O-])=O)=C1Cl WMWBBXKLYSGKDY-UHFFFAOYSA-M 0.000 description 1
- PPKIJAQKBAYNNL-UHFFFAOYSA-M sodium;4-(2,4-dichlorophenoxy)butanoate Chemical compound [Na+].[O-]C(=O)CCCOC1=CC=C(Cl)C=C1Cl PPKIJAQKBAYNNL-UHFFFAOYSA-M 0.000 description 1
- GABUSZPTCJGKGB-UHFFFAOYSA-M sodium;4-(4-chloro-2-methylphenoxy)butanoate Chemical group [Na+].CC1=CC(Cl)=CC=C1OCCCC([O-])=O GABUSZPTCJGKGB-UHFFFAOYSA-M 0.000 description 1
- JRQGDDUXDKCWRF-UHFFFAOYSA-M sodium;n-(2-methoxycarbonylphenyl)sulfonyl-4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carboximidate Chemical compound [Na+].O=C1N(C)C(OCCC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1C(=O)OC JRQGDDUXDKCWRF-UHFFFAOYSA-M 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- FZMKKCQHDROFNI-UHFFFAOYSA-N sulfometuron Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 FZMKKCQHDROFNI-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000005537 sulfoxonium group Chemical group 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 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
- BCQMBFHBDZVHKU-UHFFFAOYSA-N terbumeton Chemical compound CCNC1=NC(NC(C)(C)C)=NC(OC)=N1 BCQMBFHBDZVHKU-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- AWDBHOZBRXWRKS-UHFFFAOYSA-N tetrapotassium;iron(6+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+6].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] AWDBHOZBRXWRKS-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 1
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- GLDAZAQRGCSFNP-UHFFFAOYSA-N thiencarbazone Chemical compound O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=C(C)SC=C1C(O)=O GLDAZAQRGCSFNP-UHFFFAOYSA-N 0.000 description 1
- SMZMHUCIDGHERP-UHFFFAOYSA-N thieno[2,3-b]pyridine Chemical compound C1=CN=C2SC=CC2=C1 SMZMHUCIDGHERP-UHFFFAOYSA-N 0.000 description 1
- GDQBPBMIAFIRIU-UHFFFAOYSA-N thieno[2,3-c]pyridine Chemical compound C1=NC=C2SC=CC2=C1 GDQBPBMIAFIRIU-UHFFFAOYSA-N 0.000 description 1
- DDWBRNXDKNIQDY-UHFFFAOYSA-N thieno[2,3-d]pyrimidine Chemical compound N1=CN=C2SC=CC2=C1 DDWBRNXDKNIQDY-UHFFFAOYSA-N 0.000 description 1
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 1
- MKYRMMMSZSVIGD-UHFFFAOYSA-N thieno[3,2-c]pyridine Chemical compound N1=CC=C2SC=CC2=C1 MKYRMMMSZSVIGD-UHFFFAOYSA-N 0.000 description 1
- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- 125000001425 triazolyl 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
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- MCVUKOYZUCWLQQ-UHFFFAOYSA-N tridecylbenzene Chemical class CCCCCCCCCCCCCC1=CC=CC=C1 MCVUKOYZUCWLQQ-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229940117958 vinyl acetate Drugs 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
- A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
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- 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
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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
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Definitions
- the present invention relates to pyridine compounds of the general formula (I) defined below and to their use as herbicides. Moreover, the invention relates to compositions for crop protection and to a method for controlling unwanted vegetation.
- the present invention provides the pyridine compounds of formula (I)
- the dotted line ( ) is a single bond or a double bond
- R 1 is Ci-C6-alkyl, Ci-C6-haloalkyl, hydroxy-Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- C6-alkynyl, C3-C6-haloalkynyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C6-haloalkoxy, C3-C6- cycloalkoxy, C3-C6-halocycloalkoxy, C3-C6-cycloalkenyloxy, C3-C6-halocycloalkenyloxy, Ci-C6-alkylthio, Ci-C6-haloalkyl
- R 2 is d-Ce-alkyl, Ci-C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, Ci-C 6 -alkoxy-C 2 -C 6 - alkenyl, Ci-C6-alkoxy-C2-C6-haloalkenyl, Ci-C6-haloalkoxy-C2-C6-alkenyl, Ci-C6-haloal- koxy-C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, CrC 6 -alkoxy-C2-C6-alkynyl, Ci- C6-alkoxy-C3-C6-haloalkynyl, CrC6-haloalkoxy-C2-C6-alkynyl, Ci-C6-haloalkoxy-C3-C6-haloalkyny
- cyclic groups of R 2 are unsubstituted or substituted by R c ;
- acyclic aliphatic groups of R 2 are unsubstituted or substituted by R d .
- R b is d-Ce-alkyl, Ci-C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 - haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, C3-C6-halocy- cloalkenyl, Ci-C6-alkoxycarbonyl-Ci-C6-alkyl, Ci-C6-haloalkoxycarbonyl-Ci-C6-alkyl, Ci C6-alkoxycarbonyl-Ci-C6-haloalkyl, Ci-C6-haloalkoxycarbonyl-Ci-C6-haloalkyl, C1-C6- alkylcarbonyl, Ci-C6-
- R c is halogen, CN, NO2, Ci-Ce-alkyl, d-Ce-haloalkyl, hydroxy, d-Ce-alkoxy or Ci-Ce- haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, or Ci-C6-alkylsulfonyl;
- R d is phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl; wherein the substituent R d is unsubstituted or substituted by R e ;
- R e is halogen, CN, NO2, Ci-Ce-alkyl, d-Ce-haloalkyl, hydroxy, d-Ce-alkoxy or Ci-Ce- haloalkoxy, Ci-C6-alkylsulfonyl;
- Z is a 9 or 10 membered bicyclic ring comprising A;
- A is C * , CR 3 , NR 3A , N, O, or S;
- C * is a bridge carbon of the bicyclic ring Z
- R 3 is halogen, CN, CHO, N0 2 , Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-C 6 -alkylcarbonyl, C 2 -C 6 - alkenyl, C 2 -C6-haloalkenyl, C 2 -C6-alkenyl, C 2 -C6-haloalkenyl, Ci-C6-alkoxy, Ci-C6-haloal- koxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio, C1-C6- haloalkylthio, NH2, (Ci-C6-alkyl
- R 3A is H, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-C 6 -alkylcarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C3-C6-alkenyloxy, C3- C6-haloalkenyloxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, Ci-C6-alkoxy-CrC6-alkoxy, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio, Ci-C6-haloalkylthio, NH 2 , (Ci-C6-alkyl)amino, di(Ci- C6-alkyl)amino, (Ci
- R 4 is halogen, CN, CHO, N0 2 , Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-C 6 -alkylcarbonyl, C 2 -C 6 - alkenyl, C2-C6-haloalkenyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C6-alkoxy, Ci-C6-haloal- koxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio, C1-C6- haloalkylthio, NH2, (Ci-C6-alkyl)amino, di
- R a is halogen, CN, NO2, Ci-Ce-alkyl, Ci-Ce-haloalkyl, d-Ce-alkoxy, or d-Ce-haloalkoxy; m is 0, 1 , 2, or 3;
- the present invention also provides use of the pyridine compounds of formula (I) as described herein including agriculturally acceptable salts or derivatives of compounds of formula (I) having an acidic functionality, as herbicide.
- pyridine compounds of formula (I) according to the invention can be prepared by standard processes of organic chemistry, e.g. by the following processes:
- Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mix- tures of Cs-Cs-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), dioxane, anisole and tet- rahydrofuran (THF), and also dimethyl sulfoxide (DMSO), dimethylformamide (DMF) and dime- thylacetamide (DMAC), particularly preferably diethyl ether, dioxane and THF.
- aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mix- tures of Cs-Cs-alkanes
- aromatic hydrocarbons such as toluene,
- Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as lithium hydride (LiH), sodium hydride (NaH), potassium hydride (KH) and calcium hydride (CaH), alkali metal amides, such as lithium hexamethyidisilazide (LHMDS) and lithium diisopropylamide (LDA), organometallic compounds, in particular alkali metal alkyls, such as methyllithium (MeLi), butyllithium (BuLi) and phenyllithium (PhLi), and also alkali metal and alkaline earth metal alkoxides, such as sodium methoxide (NaOCHs), sodium ethoxide (NaOC2H5), potassium ethoxide (KOC2H5), potassium tert-butoxide ( BuOK), potassium tert- pentoxide and dimethoxymagnesium, moreover organic
- tertiary amines such as tri- methylamine (TMA), triethylamine (TEA), diisopropylethylamine (DIPEA) and N-methylpiperi- dine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines. Particular preference is given to NaH, LHMDS and lithium diisopropylamide (LDA).
- the bases are generally employed in equimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
- the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to employ an excess of base and/or the electrophile, based on the pyridine compounds (I).
- the elimination of the alcohol of the pyridine (II) is usually carried out at temperatures from -100 °C to the boiling point of the reaction mixture, preferably from 0 °C to 120 °C, particularly preferably from 20 °C to 100 °C, in an inert solvent optionally in the presence of an acid.
- Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, and also DMSO, DMF and DMAC, particularly preferably toluene and o-xylene.
- aromatic hydrocarbons such as toluene, o-, m- and p-xylene
- ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, and also DMSO, DMF and DMAC, particularly preferably toluene and o-xylene.
- Suitable acids are inorganic acids, such as HCI, HBr, sulfuric acid; organic acids p-toluenesul- fonic acid, benzene sulfonic acid, pyridinium p-toluol sulfonic acid, methanesulfonic acid, acetic acid; preferably p-toluenesulfonic acid and HCI.
- the acids are generally employed in equimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
- the oxidation of the olefin (IV) to the diol (V) is usually carried out at temperatures of from -100 °C to the boiling point of the reaction mixture, preferably from 0 °C to 120 °C, particularly preferably from 20 °C to 100 °C, in an inert solvent.
- the reaction may in principle be carried out in substance. However, preference is given to reacting the pyridines (IV) with the oxidant in an organic solvent.
- Suitable in principle are all solvents which are capable of dissolving the pyridines (IV) and the oxidant at least partly and preferably fully under the reaction conditions.
- Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, and also DMSO, DMF and DMAC, particularly preferably TBME, THF It is also possible to use mixtures of the solvents mentioned.
- Suitable oxidants are e.g. potassium permanganate, potassium perruthenate, osmium tetrox- ide and other osmium salts, like potassium osmate.
- the oxidant can be used in equimolar amounts or in catalytic amounts together with a reoxidant like N-methylmorpholine-N-oxide or potassium hexacyanoferrate in stochiometric amounts or in excess.
- the reaction may in principle be carried out in substance. However, preference is given to reacting the pyridines (VI) with the boronic acid or ester in an organic solvent with or without water as co-solvent. Suitable in principle are all solvents which are capable of dissolving the pyridines (VI) and the boronic acid or ester at least partly and preferably fully under the reaction conditions.
- suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, 0-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, tert.
- aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, 0-, m- and p-xylene
- ethers such as diethyl ether, diisopropyl ether, tert.
- TBME -butyl methylether
- anisole and THF nitriles such as acetonitrile and propionitrile
- dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, 1 ,3-dimethyl-2-imidaz- olidinone (DMI), ⁇ , ⁇ '-dimethylpropylene urea (DMPU), DMSO and NMP.
- suitable metal-containing bases are inorganic compounds including metal-con- taining bases such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH) 3 ; alkali metal and alkaline earth metal oxide, and other metal oxides, such as U2O, Na20, K2O, MgO, and CaO, Fe2C>3, Ag2 ⁇ D; alkali metal and alkaline earth metal carbonates such as U2CO3, Na2CC>3, K2CO3, CS2CO3, MgCC>3, and CaCC , as well as alkali metal bicarbonates such as IJHCO3, NaHCC , KHCO3; alkali metal and alkaline earth metal phosphates such as K3PO4, Ca3(P0 4 )2; alkali metal and alkaline earth metal acetates such as sodium acetate or potassium acetate.
- base as used herein also includes mixtures of two or more, preferably two of the above bases. Particular preference is given to the use of one base.
- the bases are used preferably from 1 to 10 equivalents based on the pyridine (VI), more pref- erably from 1.0 to 5.0 equivalents based on the pyridine (VI), most preferably from 1.2 to 2.5 equivalents based on the pyridine (VI).
- the reaction of the pyridines (VI) with the phenyl boronic acid or ester is carried out in the presence of a catalyst.
- suitable catalysts include e.g., palladium based catalysts like, e.g., Palladium(ll)acetate, tetrakis(triphenylphosphine)palladium(0), bis(tri- phenylphosphine)palladium(ll)chloride, or (1 ,1 ,-bis(diphenylphosphino)ferrocene)-dichloropalla- dium(ll), and optionally suitable additives such as, e.g., phosphines like, e.g., P(o-tolyl)3, tri- phenylphosphine, or BINAP (2,2'-Bis(diphenylphospino)-1 ,1 '-binaphthyl).
- the amount of catalyst is usually 0.01 to 10 mol % (0.0001 to 0.1 equivalents) based on the pyridine (VI).
- Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of Cs-Ce-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, and also DMSO, DMF and DMAC, particularly preferably diethyl ether, dioxane and THF.
- aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Ce-alkanes
- aromatic hydrocarbons such as toluene, o-, m- and p-xylene
- ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF
- Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH , alkali metal amides, such as lithium diiso- propylamide, lithium hexamethyidisilazide, lithium 2,2,6,6-tetramethylpiperidide, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi , and also alkali metal and alkaline earth metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide, potassium tert-pentoxide and dimethoxymagnesium, moreover organic bases, e.g.
- organic bases e.g.
- tertiary amines such as trimethylamine (TEA), triethylamine (TMA), diiso- propylethylamine (DIPEA) and N-methylpiperidine, pyridine, substituted pyridines, such as col- lidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines.
- TEA trimethylamine
- TMA triethylamine
- DIPEA diiso- propylethylamine
- N-methylpiperidine pyridine
- substituted pyridines such as col- lidine, lutidine and 4-dimethylaminpyridine
- bicyclic amines Particular preference is given to sodium hydride, lithium 2,2,6,6-tetramethylpiperidide and lithium diisopropylamide (LDA).
- the bases are generally employed in equimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
- Pyridine compounds (VIII), with R equals alkyl, haloalkyl, alkoxy or haloalkoxy, can be ob- tained by reacting respective pyridine compounds of formula (IX) with base and an electrophile (X).
- Electrophile (X) can be an alkyl-, alkenyl- or alkynyl-halide, e.g. methyl iodide, allyl bromide or propargyl bromide, or a halogenating agent, e.g.
- the reaction of the pyridine (IX) with the electrophile is usually carried out at temperatures of from -100 °C to the boiling point of the reaction mixture, preferably from -80 °C to 80 °C, particularly preferably from -80 °C to 30 °C, in an inert organic solvent in the presence of a base.
- Suitable in principle are all solvents which are capable of dissolving the pyridine (IX) and the electrophile (X) at least partly and preferably fully under the reaction conditions.
- suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF, nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, 1 ,3-dimethyl-2-imidazolidinone (DMI), ⁇ , ⁇ '- dimethylpropylene urea (DMPU), and NMP.
- aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene
- ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane,
- Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth metal alkoxides, such as NaOCH3, NaOC2Hs, KOC2H5, tBuOK, potassium tert-pentoxide and dimethoxymagnesium, moreover organic bases, e.g.
- inorganic compounds such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth
- tertiary amines such as TMA, TEA, DIPEA and N-methylpiperidine
- pyridine substituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines.
- Particular preference is given to NaH, lithium hexamethyldisilazide and LDA.
- the bases are generally employed in equimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
- the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to employ an excess of base and/or the electrophile (X), based on the pyridine
- the reaction of the pyridine (I) with the electrophile (XII) is usually carried out at temperatures of from -100 °C to the boiling point of the reaction mixture, preferably from -80 °C to 80 °C, par- ticularly preferably from -80 °C to 30 °C, in an inert organic solvent in the presence of a base.
- Suitable in principle are all solvents which are capable of dissolving the pyridine (I) and the electrophile (XII) at least partly and preferably fully under the reaction conditions.
- suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, 0-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, DMI, DMPU, DMSO and NMP.
- aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, 0-, m- and p-xylene
- ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF
- dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, DMI, DMPU, DMSO and NMP.
- Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth metal alkoxides, such as NaOCH3, NaOC2Hs, KOC2H5, tBuOK, potassium tert-pentoxide and dimethoxymagnesium, moreover organic bases, e.g.
- inorganic compounds such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth
- tertiary amines such as TMA, TEA, DIPEA and N-methylpiperidine
- pyridine substituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines.
- Particular preference is given to NaH, lithium hexamethyldisilazide and LDA.
- the bases are generally employed in equimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
- the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to employ an excess of base and/or the electrophile (XII), based on the pyridine
- the pyridines of formula (XIV) can be obtained by reacting respective pyridines of formula (XIII) with a reducing agent such as LAH or DIBAIH.
- the reduction of pyridines (XIII) is usually carried out from - 80 °C to the boiling point of the reaction mixture, preferably from -20 °C to 60 °C, particularly preferably from 0 °C to 25 °C, in an inert organic solvent.
- Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mix- tures of Cs-Cs-alkanes, aromatic hydrocarbons, such as toluene, 0-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, and also DMSO, DMF and DMAC, particularly preferably diethyl ether, dioxane and THF.
- aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mix- tures of Cs-Cs-alkanes
- aromatic hydrocarbons such as toluene, 0-, m- and p-xylene
- ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and
- Examples of reducing agents for pyridines (XIII) include LAH, DIBALH, LiBH 4 or Lithium tri- ethylborohydride.
- Preferred agents include LAH and DIBALH.
- the hydride-source is used preferably from 1 to 10 equivalents based on the pyridine (XIII), more preferably from 1.0 to 5.0 equivalents based on the pyridine (XIII), most preferably from 1.2 to 2.5 equivalents based on the pyridine (XIII).
- the end of the reaction can easily be determined by the skilled worker by means of routine methods.
- reaction mixtures are worked up in a customary manner, e.g. by mixing with water, separation of the phases and, if appropriate, chromatographic purification of the crude product.
- Some of the intermediates and end products are obtained in the form of viscous oils, which can be purified or freed from volatile components under reduced pressure and at moderately elevated temperature.
- purification can also be carried out by recrystallization or digestion.
- the pyridines of formula (XIII) can be obtained by reacting respective pyridines of formula (XV) with boronic acids/esters of formula (XVI):
- the reaction of pyridines (XV) with boronic acids/esters (XVI) is usually carried out from 0 °C to the boiling point of the reaction mixture, preferably from 15 °C to 1 10 °C, particularly preferably from 40 °C to 100 °C, in an inert organic solvent in the presence of a base and a catalyst.
- the reaction may in principle be carried out in substance. However, preference is given to reacting the pyridines (XV) with the boronic acids/esters (XVI) in an organic solvent with or without water as co-solvent.
- Suitable in principle are all solvents which are capable of dissolving the pyridines (XV) and the boronic acids (XVI) at least partly and preferably fully under the reaction conditions.
- suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, DMI, DMPU, DMSO and NMP.
- aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene
- ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF
- dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, DMI, DMPU, DMSO and NMP
- suitable metal-containing bases are inorganic compounds including metal-containing bases such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH) 3 ; alkali metal and alkaline earth metal oxide, and other metal oxides, such as U2O, Na20, K2O, MgO, and CaO, Fe2C>3, Ag 2 0; alkali metal and alkaline earth metal carbonates such as U2CO3, Na2CC>3, K2CO3, Cs 2 C0 3 , MgC0 3 , and CaC0 3 , as well as alkali metal bicarbonates such as LiHC0 3 , NaHC0 3 , KHCO3; alkali metal and alkaline earth metal phosphates such as K3PO4, Ca3(P0 4 )2; alkali metal and alkaline earth metal acetates such as sodium acetate or potassium acetate.
- base as used herein also includes mixtures of two or more, preferably two of the above bases. Particular preference is given to the use of one base.
- the bases are used preferably from 1 to 10 equivalents based on the pyridine (XV), more preferably from 1.0 to 5.0 equivalents based on the pyridine (XV), most preferably from 1.2 to 2.5 equivalents based on the pyridine (XV).
- the reaction of the pyridines (XV) with the boronic acids/esters (XVI) is carried out in the pres- ence of a catalyst.
- suitable catalysts include e.g., palladium based catalysts like, e.g., palladium(ll)acetate, tetrakis(triphenylphosphine)- palladium(O), bis(triphenylphosphine)pal- ladium(ll)chloride or (1 ,1 ,-bis(diphenylphosphino)- ferrocene)-dichloropalladium(ll), and optionally suitable additives such as, e.g., phosphines like, e.g., P(o-tolyl)3, triphenylphosphine or BINAP (2,2'-Bis(diphenylphospino)-1 ,1 '-binaphthyl).
- the amount of catalyst is usually 0.01 to 20 mol % (0.0001 to 0.2 equivalents) based on the pyridine (XV).
- halopyridines XV are known from the literature (e.g. WO 201 1 154327), are commercially available or can be prepared by known procedures.
- the boronic acids/esters XVI required for the preparation of pyridines of formula (XIII) are commercially available, known from literature or can easily prepared analogously to published procedures (e.g. Kamei et al. Tetrahedron Lett. 2014, 55, 4245 - 4247).
- the reaction of pyridines (XIII) with a metal organic species is usually carried out from - 80 °C to the boiling point of the reaction mixture, preferably from -20 °C to 60 °C, particularly preferably from -20 °C to 25 °C, in an inert organic solvent.
- Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, and also DMSO, DMF and DMAC, particularly preferably diethyl ether, dioxane and THF.
- aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-alkanes
- aromatic hydrocarbons such as toluene, o-, m- and p-xylene
- ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF
- metal organic species for the synthesis of pyridines are Grignard reagents like R'MgCI, R'MgBr or R'Mgl, lithium organic species, aluminum organic species like R'sAI, R' 2 AIX and R'AIX 2 , titanium organic species like R' 4 Ti, R' 3 TiX, R' 2 TiX 2 and RTiX 3 ,
- Preferred agents include Grignard reagents and lithium organic species.
- the metal organic species is used preferably from 2 to 10 equivalents based on the pyridine (XIII), more preferably from 2.0 to 5.0 equivalents based on the pyridine (XIII), most preferably from 2.0 to 3.0 equivalents based on the pyridine (XIII).
- the reaction of pyridines (XVIII) with a metal organic species is usually carried out from - 80 °C to the boiling point of the reaction mixture, preferably from -20 °C to 60 °C, particularly preferably from -20 °C to 25 °C, in an inert organic solvent.
- Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, and also DMSO, DMF and DMAC, particularly preferably diethyl ether, dioxane and THF.
- aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-alkanes
- aromatic hydrocarbons such as toluene, o-, m- and p-xylene
- ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF
- metal organic species for the synthesis of pyridines are Grignard reagents like R'MgCI, R'MgBr or R'Mgl, lithium organic species, aluminum organic species like R'sAI, R' 2 AIX and R'AIX 2 , titanium organic species like R' 4 Ti, R' 3 TiX, R' 2 TiX 2 and RTiX 3 ,
- Preferred agents include Grignard reagents and lithium organic species.
- the metal organic species is used preferably from 2 to 10 equivalents based on the pyridine (XVIII), more preferably from 2.0 to 5.0 equivalents based on the pyridine (XVIII), most preferably from 2.0 to 3.0 equivalents based on the pyridine (XVIII).
- the pyridines of formula (XVIII) can be obtained by oxidizing respective pyridines of formula (XI
- the oxidation of pyridines (XIV) is usually carried out from - 80 °C to the boiling point of the reaction mixture, preferably from -20 °C to 100 °C, particularly preferably from 0 °C to 75 °C, in an inert organic solvent.
- the reaction may in principle be carried out in substance. However, preference is given to re- acting the pyridines (XIV) in an organic solvent.
- Suitable in principle are all solvents which are capable of dissolving the pyridines (XIV) at least partly and preferably fully under the reaction conditions.
- suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as CH 2 CI 2 , CHCI3, CCH 2 CICH 2 CI or CCI 4 , ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and tetrahydrofuran (THF), as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
- aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene
- halogenated hydrocarbons such as CH 2 CI 2 , CHCI3, CCH 2 CICH 2 CI or CCI 4
- ethers such as diethyl ether
- oxidizing agents for the synthesis of pyridines are metal oxides such as Mn0 2 , KMn0 4 , CrC or PCC, and non-metal oxides such as NaCIO, Nal0 4 or pyridine/SO-3 - complex.
- metal oxides such as Mn0 2 , KMn0 4 , CrC or PCC
- non-metal oxides such as NaCIO, Nal0 4 or pyridine/SO-3 - complex.
- Swern oxidation or the TEMPO oxidation known to a person skilled in the art can be used to obtain pyridines of formula (XVIII).
- Preferred agents include Mn0 2 , KMn0 4 and PCC, more preferred Mn0 2 .
- the oxidizing agent is used preferably from 1 to 50 equivalents based on the pyridine (XIV), more preferably from 1.0 to 20.0 equivalents based on the pyridine (XIV), most preferably from 1.0 to 10.0 equivalents based on the pyridine (XIV).
- Electrophiles can be an alkyl-, alkenyl- or alkynyl-halide, e.g. methyl iodide, allyl bromide pro- pargyl bromide, ethyl iodide, propyl bromide, or ethyl 2-bromoacetate.
- the reaction of the pyridine (XX) with the electrophile is usually carried out at temperatures of from -100 °C to the boiling point of the reaction mixture, preferably from -20 °C to 100 °C, particularly preferably from 0 °C to 30 °C, in an inert organic solvent in the presence of a base.
- Suitable in principle are all solvents which are capable of dissolving the pyridine (XX) and the electrophile at least partly and preferably fully under the reaction conditions.
- suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF, nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, DMI, DMPU, and NMP.
- aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene
- ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF
- nitriles such as acetonitrile and propionitrile
- Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LDA, LHMDS, lithium 2,2,6,6-tetramethylpiperidide (LTMP), organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth metal alkox- ides, such as NaOCH 3 , NaOC2H 5 , KOC2H5, tBuOK, potassium tert-pentoxide and dimethox- ymagnesium, moreover organic bases, e.g.
- inorganic compounds such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LDA, LHMDS, lithium 2,2,6,6-tetramethylpiperidide (LTMP
- tertiary amines such as TMA, TEA, DIPEA and N- methylpiperidine
- pyridine substituted pyridines, such as collidine, lutidine and 4-dimethyla- minpyridine, and also bicyclic amines.
- Particular preference is given to NaH, LTMP and LDA.
- the bases are generally employed in equimolar amounts; however, they can also be em- ployed in catalytic amounts, in excess or, if appropriate, as solvents.
- the pyridines of formula (I) can also be obtained by reacting respective pyridines of formula (XXII), obtained e.g. in analogy to Synlett, (5), 808-810, 2002, with boronic acids/esters of formula (XXIII):
- reaction of pyridines (XXII) with boronic acids/esters (XXIII) is usually carried out from 0 °C to the boiling point of the reaction mixture, preferably from 15 °C to 1 10 °C, particularly preferably from 40 °C to 100 °C, in an inert organic solvent in the presence of a base and a catalyst.
- reaction may in principle be carried out in substance. However, preference is given to re- acting the pyridines (XXII) with the boronic acids/esters (XXIII) in an organic solvent with or without water as co-solvent.
- Suitable in principle are all solvents which are capable of dissolving the pyridines (XXII) and the boronic acids (XXIII) at least partly and preferably fully under the reaction conditions.
- suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, DMI, DMPU, and NMP.
- aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene
- ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF
- dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, DMI, DMPU, and NMP.
- suitable metal-containing bases are inorganic compounds including metal-con- taining bases such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH) 3 ; alkali metal and alkaline earth metal oxide, and other metal oxides, such as Li 2 0, Na20, K 2 0, MgO, and CaO, Fe2C>3, Ag2 ⁇ D; alkali metal and alkaline earth metal carbonates such as U2CO3, Na2CC>3, K2CO3, CS2CO3, MgCC>3, and CaCC , as well as alkali metal bicarbonates such as LiHCC>3, NaHCC , KHCO3; alkali metal and alkaline earth metal phosphates such as K3PO4, Ca3(P0 4 )2; alkali metal and alkaline earth metal acetates such as sodium acetate or potassium acetate.
- base as used herein also includes mixtures of two or more, preferably two of the above compounds. Particular preference is given to the use of one base.
- the bases are used preferably from 1 to 10 equivalents based on the pyridine (XXII), more preferably from 1 .0 to 5.0 equivalents based on the pyridine (XXII), most preferably from 1 .2 to 2.5 equivalents based on the pyridine (XXII).
- a catalyst examples include e.g., palladium based catalysts like, e.g., palladium(ll)acetate, tetrakis(triphenylphosphine)- palladium(O), bis(tri- phenylphosphine)palladium(ll)chloride or (1 ,1 ,-bis(diphenylphosphino)- ferrocene)-dichloropalla- dium(ll), and optionally suitable additives such as, e.g., phosphines like, e.g., P(o-tolyl)3, tri- phenylphosphine or BINAP (2,2'-Bis(diphenylphospino)-1 ,1 '-binaphthyl).
- palladium based catalysts like, e.g., palladium(ll)acetate, tetrakis(triphenylphosphine)- palladium(O), bis(
- the amount of catalyst is usually 0.01 to 20 mol % (0.0001 to 0.2 equivalents) based on the pyridine (XXII).
- the end of the reaction can easily be determined by the skilled worker by means of routine methods.
- reaction mixtures are worked up in a customary manner, e.g. by mixing with water, separation of the phases and, if appropriate, chromatographic purification of the crude product.
- Some of the intermediates and end products are obtained in the form of viscous oils, which can be purified or freed from volatile components under reduced pressure and at moderately elevated temperature.
- the boronic acids/esters (XXIII) required for the preparation of pyridines of formula (I) are commercially available, known from literature or can easily prepared analogously to published procedures (e.g. Kamei et al. Tetrahedron Lett. 2014, 55, 4245 - 4247).
- the present invention also provides agrochemical compositions comprising at least one pyridine compounds of formula (I) and auxiliaries customary for formulating crop protection agents.
- the present invention furthermore provides a method for controlling unwanted vegetation where a herbicidal effective amount of at least one pyridine compounds of formula (I) is allowed to act on plants, their seeds and/or their habitat.
- Application can be done before, during and/or after, preferably during and/or after, the emergence of the undesirable plants.
- pyridine compounds of formula (I) as described herein are capable of forming geomet- rical isomers, e.g. E/Z isomers, it is possible to use both, the pure isomers and mixtures thereof, in the compositions according to the invention.
- pyridine compounds of formula (I) as described herein have one or more centres of chi- rality and, as a consequence, are present as enantiomers or diastereomers, it is possible to use both, the pure enantiomers and diastereomers and their mixtures, in the compositions according to the invention.
- pyridine compounds of formula (I) as described herein have ionisable functional groups, preferably an acidic functionality, they can also be employed in the form of their agriculturally acceptable salts. Suitable are, in general, the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the activity of the active compounds.
- Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four H atoms are replaced by Ci-C4-alkyl, hydroxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci- C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl, preferably ammonium, methyl-ammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetrae- thylamm-onium
- Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogen- sulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of Ci-C4-al- kanoic acids, preferably formate, acetate, propionate and butyrate.
- Pyridine compounds of formula (I) as described herein having an acidic functionality can be employed, if applicable, in the form of the acid, in the form of an agriculturally suitable salt, whereby the cations are defined as mentioned above, or else in the form of an agriculturally acceptable derivative, e.g. as amides, such as mono- and di-Ci-C6-alkylamides or arylamides, as esters, e.g. as allyl esters, propargyl esters, Ci-Cio-alkyl esters, alkoxyalkyl esters, tefuryl ((tet- rahydrofuran-2-yl)methyl) esters and also as thioesters, e.g.
- amides such as mono- and di-Ci-C6-alkylamides or arylamides
- esters e.g. as allyl esters, propargyl esters, Ci-Cio-alkyl esters, alk
- Ci-Cio-alkylthio esters Preferred mono- and di-Ci-C6-alkylamides are the CH3 and the dimethylamides.
- Preferred arylamides are, e.g., the anilides and the 2-chloroanilides.
- Preferred alkyl esters are, e.g., the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1 -methylhexyl), meptyl (1-methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters.
- Ci-C4-alkoxy-Ci-C4-alkyl esters are the straight-chain or branched Ci-C4-alkoxy ethyl esters, e.g. the 2-methoxyethyl, 2-ethoxyethyl, 2- butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropyl ester.
- An example of a straight-chain or branched Ci-Cio-alkylthio ester is the ethylthio ester.
- the organic moieties mentioned in the definition of the variables R 1 , R 2 , A, Z, R 3 , R 3A , and R 4 are - like the term halogen - collective terms for individual enumerations of the individual group members.
- the term halogen denotes in each case F, CI, Br, or I .
- All hydrocarbon chains, e.g. all alkyl, alkenyl, alkynyl, alkoxy chains can be straight-chain or branched, the prefix C n -C m denoting in each case the possible number of carbon atoms in the group.
- - CrC 4 -alkyl e.g. CH 3 , C 2 H 5 , n-propyl, CH(CH 3 ) 2 , n-butyl, CH(CH 3 )-C 2 H 5 , CH 2 -CH(CH 3 ) 2 , and C(CH 3 ) 3 ;
- Ci-C6-alkyl Ci-C4-alkyl as mentioned above, and also, e.g., n-pentyl, 1-methylbutyl, 2- methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, n-hexyl, 1 ,1 -dimethylpropyl, 1 ,2- dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1-dimethyl- butyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethyl- butyl, 1-ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-tri methyl propyl, 1 ,2,2-trimethylpropyl, 1 -ethyl-1
- Ci-C4-haloalkyl Ci-C4-alkyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, e.g., chloromethyl, dichloromethyl, trichloromethyl, flu- oromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluo- romethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro- 2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl
- Ci-C6-haloalkyl Ci-C4-haloalkyl as mentioned above, and also, e.g., 5-fluoropentyl, 5- chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl, and dodecafluorohexyl;
- C3-C6-cycloalkyl monocyclic saturated hydrocarbons having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
- C3-C6-alkenyl e.g. 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-bu- tenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl, 1- pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1 -butenyl, 2-methyl-1 -butenyl, 3-methyl-
- C3-C6-haloalkenyl a C3-C6-alkenyl substituent as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, e.g. 2-chloroprop-2-en-1-yl, 3-chlo- roprop-2-en-1 -yl, 2,3-dichloroprop-2-en-1 -yl, 3,3-dichloroprop-2-en-1-yl, 2,3,3-trichloro-2-en-1-yl, 2,3-dichlorobut-2-en-1-yl, 2-bromoprop-2-en-1-yl, 3-bromoprop-2-en-1-yl, 2,3-dibromoprop-2- en-1-yl, 3,3-dibromoprop-2-en-1 -yl, 2,3,3-tribromo-2-en-1-yl, or 2,3-dibromobut-2-en-1 -yl;
- C3-C6-alkynyl e.g. 1-propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1-methyl-2- propynyl, 1 -pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl,
- C2-C6-alkynyl C3-C6-alkynyl as mentioned above and also ethynyl;
- C3-C6-haloalkynyl a C3-C6-alkynyl radical as mentioned above which is partially or fully substituted by F, CI, Br and/or I, e.g. 1 ,1 -difluoroprop-2-yn-1 -yl, 3-chloroprop-2-yn-1-yl, 3-bromo- prop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1 -yl, 1 ,1 -difluorobut- 2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1 -yl, 5-iodopent-4-yn-1 -yl, 6-fluorohex-4-yn-1 -yl, or 6-iodohex-5-yn-1 -yl;
- Ci-C4-alkoxy e.g. methoxy, ethoxy, propoxy, 1 -methylethoxy butoxy, 1 -methylpropoxy, 2-methylpropoxy, and 1 ,1 -dimethylethoxy;
- Ci-C6-alkoxy Ci-C4-alkoxy as mentioned above, and also, e.g., pentoxy, 1-methylbut- oxy, 2-methylbutoxy, 3-methoxyl butoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dime- thylpropoxy, 1 -ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1 -dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbut- oxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1 ,1 ,2-trime- thylpropoxy, 1 ,2, 2-tri methyl propoxy, 1-ethyl-1-methylpropoxy, and 1 -ethyl-2-methylprop
- Ci-C4-haloalkoxy a Ci-C4-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., e.g., fluoromethoxy, difluorometh- oxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloro- ethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluo roethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pen- tafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy
- Ci-C6-haloalkoxy a Ci-C4-haloalkoxy as mentioned above, and also, e.g., 5-fluoro- pentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluoro- hexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy and dodecafluorohexoxy;
- Ci-C4-alkylthio e.g. methylthio, ethylthio, propylthio, 1 -methylethylthio, butylthio, 1- methylpropylthio, 2-methylpropylthio, and 1 ,1-dimethylethylthio;
- Ci-C6-alkylthio Ci-C4-alkylthio as mentioned above, and also, e.g., pentylthio, 1 -methyl- butylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hex- ylthio, 1 ,1 -dimethylpropylthio, 1 ,2-dimethylpropylthio, 1 -methylpentylthio, 2-methylpentylthio, 3- methylpentylthio, 4-methylpentylthio, 1 ,1-dimethylbutylthio, 1 ,2-dimethylbutylthio, 1 ,3-dimethyl- butylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1 -ethylbutylthi
- (Ci-C4-alkyl)amino e.g. methylamino, ethylamino, propylamino, 1 -methylethylamino, bu- tylamino, 1-methylpropylamino, 2-methylpropylamino, or 1 ,1-dimethylethylamino;
- (Ci-C6-alkyl)amino (Ci-C4-alkylamino) as mentioned above, and also, e.g., pentyl- amino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino, 1 -ethylpropylamino, hexylamino, 1 ,1-dimethylpropylamino, 1 ,2-dimethylpropylamino, 1-methyl- pentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1 ,1-dimethyl- butylamino, 1 ,2-dimethylbutylamino, 1 ,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dime- thylbutyl-amino 3,3-dimethylbutylamino, 1 -eth
- di(Ci-C4-alkyl)amino e.g. N,N-dimethylamino, ⁇ , ⁇ -diethylamino, N,N-di(1-methyl- ethyl)amino, N,N-dipropylamino, ⁇ , ⁇ -dibutylamino, N,N-di(1-methylpropyl)amino, N,N-di(2-me- thyl-propyl)amino, N,N-di(1 ,1-dimethylethyl)amino, N-ethyl-N-methylamino, N-methyl-N-propyl- amino, N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(1 -methylpropylamino, N-methyl-N-(2-methylpropyl)amino, N-(1 ,1-
- Ci-C6-alkylsulfonyl (Ci-C6-alkyl-S(0)2-) : e.g. methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1 -methylpropylsulfonyl, 2-methyl-propylsulfonyl, 1 ,1 -di- methylethylsulfonyl, pentylsulfonyl, 1 -methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutyl- sulfonyl, 1 ,1-dimethylpropylsulfonyl, 1 ,2-dimethylpropylsulfonyl, 2,2-dimethylpropyl-sulfonyl, 1- ethylpropylsulfon
- C3-C6-cycloalkyl a monocyclic saturated hydrocarbon having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
- C3-C6-cycloalkenyl 1-cyclopropenyl, 2-cyclopropenyl, 1 -cyclobutenyl, 2-cyclobutenyl, 1 - cyclopentenyl, 2-cyclopentenyl, 1 ,3-cyclopentadienyl, 1 ,4-cyclopentadienyl, 2,4-cyclopentadi- enyl, 1 -cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1 ,3-cyclohexadienyl, 1 ,4-cyclohexadienyl, or 2,5-cyclohexadienyl;
- bicyclic ring a 9- to 10-membered bicyclic ring: a partially or fully unsaturated 9- to 10- membered carbocyclic system wherein two partially or fully unsaturated carbocyclic rings are fused with each other through 2 ring members, and which in addition to carbon atoms and independent of their position in the ring can comprise as ring members 1 to 4 nitrogen atoms, or 1 or 2 oxygen atoms, or 1 or 2 oxygen atoms and 1 to 2 nitrogen atoms, or 1 or 3 sulfur atoms, or 1 to 4 nitrogen atoms and an oxygen atom, or one to three nitrogen atoms and a sulfur atom, or one sulfur and one oxygen atom, examples of such bicyclic ring are, 2,3-dihydrobenzothio- phene, benzothiophene, 2,3-dihydrobenzofuran, benzofuran, 1 ,3-benzodioxole, 1 ,3-benzodithi- ole, 1 ,3
- heterocyclyl a 3- to 6-membered heterocyclyl: a saturated or partial unsaturated cycle having three to six ring members which comprises apart from carbon atoms one to four nitrogen atoms, or one or two oxygen atoms, or one or two sulfur atoms, or one to three nitrogen atoms and an oxygen atom, or one to three nitrogen atoms and a sulfur atom, or one sulfur and one oxygen atom, e.g.
- 6-membered partial unsaturated heterocycles like 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopy- ran-5-yl, 2H-thiopyran-6-yl, or 5,6-dihydro-4H-1 ,3-oxazin-2-yl.
- heteroaryl a 5- or 6-membered heteroaryl: monocyclic aromatic heteroaryl having 5 to 6 ring members which, in addition to carbon atoms and independent of their position in the ring, contains 1 to 4 nitrogen atoms, or 1 to 3 nitrogen atoms and an oxygen or sulfur atom, or an oxygen or a sulfur atom, e.g. 5-membered aromatic rings like furyl (e.g. 2-furyl, 3-furyl), thienyl (e.g. 2-thienyl, 3-thienyl), pyrrolyl (e.g. pyrrol-2-yl, pyrrol-3-yl), pyrazolyl (e.g.
- pyrazol-3-yl, pyra- zol-4-yl isoxazolyl (e.g. isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl), isothiazolyl (e.g. isothiazol-3- yl, isothiazol-4-yl, isothiazol-5-yl), imidazolyl (e.g. imidazole-2-yl, imidazole-4-yl), oxazolyl (e.g. oxazol-2-yl, oxazol-4-yl, oxazol-5-yl), thiazolyl (e.g.
- substituted if not specified otherwise refers to substituted by 1 , 2 or maximum pos- sible number of substituents. If substituents as defined in compounds of formula I are more than one then they are independently from each other are same or different if not mentioned otherwise.
- the substituent R 4 if present, can be present in any ring of "Z".
- acidic functionality if not specified otherwise refers to a functionality capable of do- nating a hydrogen (proton or hydrogen ion H + ), such as a carboxylic group or a sulphonic group, or, alternatively, capable of forming a covalent bond with an electron pair.
- pyridine compounds of formula (I) are suitable as herbicides.
- pyridine compounds of formula (I) and their use as herbicides, wherein the variables, either independently of one another or in combination with one another, have the following meanings:
- R 1 is Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloal- kenyloxy C3-C6-alkynyloxy, C4-C6-haloalkynyloxy, Ci-C6-alkylthio, C3-C6-cycloalkyl, wherein the cycloalkyl substituent is unsubstituted;
- R 1 is Ci-C6-alkyl, Ci-C6-alkoxy, or C3-C6-cycloalkyl, wherein the cycloalkyl substituent is unsubstituted;
- R 1 is C3-C6-cycloalkyl, wherein the cycloalkyl substituent is unsubstituted; also especially preferred R 1 is C2H5, 1-C3H7, 1-C4H9, OCH 3 , C-C3H5, or C-C4H9;
- R 1 is C2H5, OCH 3 , or C-C3H5;
- R 1 is C-C3H5.
- R 2 is C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C6-alkoxy-C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkenyl, C3-C6-cycloalkenyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-alkylidenyl, C3-C6- halocycloalkyl-Ci-C6-alkylidenyl, C3-C6-cycloalkenyl-Ci-C6-alkylidenyl, C3-C6-hydroxycycloalkyl- Ci-C6-alkyl, hydroxycycloalkenyl-Ci-C6-alkyl, Ci-C6-hydroxyalkyl, C3-C6-cycloalkyl-C2-C6-hydrox- yalkylidenyl, hydroxy
- cyclic groups of R 2 are unsubstituted or substituted by R c , and
- R 2 acyclic aliphatic groups of R 2 are unsubstituted or substituted by R d .
- R 2 is C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkenyl, C3-C6-cycloalkyl- Ci-C6-alkylidenyl, C3-C6- alocycloalkyl-Ci-C6-alkylidenyl, C3-C6- ydroxycycloalkyl-Ci-C6-alkyl, C3-C6- ydroxycycloalkyl-Ci-C6- ydroxyalkyl, C2-C6-dihydroxyalkyl, or 5- or 6-membered het- eroaryl;
- R 2 is C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkenyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-alkylidenyl, Ci-C6-hydroxyalkyl, Ci-C6-alkoxycarbonyl-Ci-C6-alkyl, C2-C6- dihydroxyalkyl, Ci-C6-dicyanoalkyl, or 5- or 6-membered heteroaryl;
- cyclic groups of R 2 are unsubstituted or substituted by R c , and
- acyclic aliphatic groups of R 2 are unsubstituted or substituted by R d .
- R 2 is C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl-Ci-C6-alkylidenyl, C3- C6-hydroxycycloalkyl-Ci-C6-alkyl, and 5- or 6-membered heteroaryl;
- R 2 is C2-C6-alkenyl, Ci-C6-hydroxyalkyl, C3-C6-cycloalkyl-Ci-C6-alkyli- denyl, C2-C6-dihydroxyalkyl, Ci-C6-dicyanoalkyl and 5- or 6-membered heteroaryl;
- R 2 is C2-C6-alkenyl, C3-C6-cycloalkyl-Ci-C6-alkylidenyl, Ci-C6-hydrox- yalkyl, C2-C6-dihydroxyalkyl, or 5- or 6-membered heteroaryl;
- cyclic groups of R 2 are unsubstituted or substituted by R c , and
- acyclic aliphatic groups of R 2 are unsubstituted or substituted by R d .
- R 2 is C2-C6-alkenyl, C3-C6-cycloalkyl-Ci-C6-alkylidenyl, or 5- or 6-membered heteroaryl;
- R 2 is Ci-C6-hydroxyalkyl, C2-C6-dihydroxyalkyl, C3-C6-cycloalkyl-Ci-C6-al- kylidenyl, or 5- or 6-membered heteroaryl;
- cyclic groups of R 2 are unsubstituted or substituted by R c , and
- acyclic aliphatic groups of R 2 are unsubstituted or substituted by R d .
- R 2 is C2-C6-alkenyl
- R 2 is C3-C6-cycloalkyl-Ci-C6-alkylidenyl
- R 2 is 5- or 6-membered heteroaryl
- R 2 is Ci-C6-hydroxyalkyl
- R 2 is C2-C6-dihydroxyalkyl
- cyclic groups of R 2 are unsubstituted or substituted by R c , and
- acyclic aliphatic groups of R 2 are unsubstituted or substituted by R d .
- R 2 is 2-furyl, 3-furyl, 2-methyl-3-furyl, 3-methyl-2-furyl, or 4-methyloxazol- 5-yl;
- R 2 is selected from R 2 -1 to R 2 -16 as shown below,
- # denotes attachment to the pyridine ring
- X and Y denotes R c which independently of each other are identical or different
- R 2 is R 2 -1 , R 2 -2, R 2 -3, R 2 -4, R 2 -5, R 2 -6, R 2 -7, or R 2 -8;
- R 2 is R 2 -9, R 2 -10, R 2 -1 1 , R 2 -13, R 2 -14, or R 2 -15;
- R 2 is R 2 -9, R 2 -10, or R 2 -15;
- R 2 is R 2 -9;
- X 1 is H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy, Ci-C6-haloal- koxy, or Ci-C6-alkylthio;
- X 1 is H, halogen, CN, Ci-C6-alkyl, OH, Ci-C6-alkoxy, or Ci-C6-alkylthio; also particularrly preferred X is H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, or Ci-C6-haloalkoxy;
- X 1 is H, halogen, CN, Ci-C4-alkyl, OH, Ci-C4-alkoxy, or Ci-C4-alkylthio; more preferred X 1 is H, CH3, C2H5, n-propyl, iso-propyl, iso-butyl, n-butyl, OH, OCH3, SCH3, F, CI, Br, or I;
- X 1 is H, CH 3 , C 2 H 5 , OH, or OCH 3 ;
- X 1 is H, CH 3 , C 2 H 5 , or SCH 3 ;
- X 1 is H, CH 3 , C2H5, F, CI, Br, or I.
- Y 1 is H, halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy, Ci-C 6 -haloal- koxy, or Ci-C6-alkylthio;
- Y 1 is H, halogen, CN, Ci-C6-alkyl, OH, Ci-C6-alkoxy, or Ci-C6-alkylthio; also particularrly preferred Y 1 is H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, or Ci-C6-haloalkoxy;
- Y 1 is H, halogen, CN, Ci-C4-alkyl, Ci-C2-fluoroalkyl, OH, Ci-C4-alkoxy, or CrC 4 -alkylthio;
- Y 1 is H, CH 3 , C2H5, n- propyl, iso-propyl, iso-butyl, n-butyl, 2-butyl, t-butyl, OH, OCH 3 , SCH 3 , F, CI, Br, or I;
- Y 1 is H, CH 3 , C2H5, n- propyl, iso-propyl, iso-butyl, n-butyl, 2-butyl, OH, or OCH 3 ;
- Y 1 is H, CH 3 , C2H5, n-propyl, iso-propyl, OH, OCH 3 , or SCH 3 ; also most preferred Y 1 is H, CH 3 , C2H5, n-propyl, iso-propyl, F, CI, Br, or I .
- R 2 is 4-methyl-5-oxazolyl, 4-ethyl-5-oxazolyl, 2,4-dimethyl-5-oxazolyl, 2- ethyl-4-methyl-5-oxazolyl, 2-methyl-4-ethyl-5-oxazolyl, or 2,4-diethyl-5-oxazolyl.
- R 2 examples of more particularly preferred R 2 are provided in Table R 2 -9, Table R 2 -10, and Table R 2 -15.
- R 2 -9 examples of particularly preferred R 2 are R 2 -9.1 to R 2 -9.676 wherein R 2 is R 2 -9 and combinations of variables X 1 and Y 1 are as defined in each row of table R2, numbering of each compound e.g. R 2 -9.1 means R 2 is R 2 -9 wherein X 1 and Y 1 are as defined in row 1 of table R2;
- Table R 2 -10 examples of particularly preferred R 2 are R 2 -10.1 to R 2 -10.676 wherein R 2 is R 2 - 10 and combinations of variables X 1 and Y 1 are as defined in each row of table R2, numbering of each compound e.g. R 2 -10.1 means R 2 is R 2 -10 wherein X 1 and Y 1 are as defined in row 1 of table R2;
- Table R 2 -15 examples of particularly preferred R 2 are R 2 -15.1 to R 2 -15.676 wherein R 2 is R 2 - 15 and combinations of variables X 1 and Y 1 are as defined in each row of table R2, numbering of each compound e.g. R 2 -15.1 means R 2 is R 2 -15 wherein X 1 and Y 1 are as defined in row 1 of table R2.
- Preferred A is CR 3 , C*.
- NR 3A N, S or O;
- A is CR 3 , C*, NR 3A , or N;
- A is S or O
- especially preferred A is C*, CR 3 or N;
- A is CR 3 ;
- Preferred Z is 9 or l Omembered bicyclic ring
- particularly preferred Z is 9 membered bicyclic ring; particularly preferred Z is 10 membered bicyclic ring; more preferred Z is selected from below groups A to O,
- Y is 5- or 6-membered partially or fully unsaturated carbocycle comprising 0, 1 , 2, or 3 heteroatoms selected from O, N, and S;
- R 3 is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
- n 0, 1 or 2;
- R 4 is halogen, CN, CrC 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy;
- X is O, S, or NR 3A ;
- R 3A is H, d-Ce-alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl, C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
- # denotes the point of attachment to the pyridine ring.
- Preferred Y is phenyl
- Y is 5- or 6-membered partially or fully unsaturated carbocycle comprising 1 , 2, or 3 heteroatoms selected from O, N, and S;
- Y is phenyl
- Y is 5-membered partially or fully unsaturated carbocycle comprising 1 , or 2 heteroatoms selected from O, N, and S;
- Y is 5-membered partially unsaturated carbocycle comprising 0, 1 , or 2 heteroatoms selected from O, N, and S, e.g. 1 ,3-dithiolane, 1 ,3-oxathiolane, 1 ,3-dioxolane, 2,3- dihydrofuran, 2,3-dihydrothiophene, or 2,3-dihydro-1 H-pyrrole; more preferably heteroatoms are selected from O and S, e.g.
- heteroatom in Y is O, e.g. 1 ,3-dioxolane, or 2,3-dihydrofuran; also most preferred heteroatom in Y is S, e.g.
- Y is 5-membered fully unsaturated carbocycle comprising 0, 1 , or 2 heteroatoms selected from O, N, and S (furan, thiophene, 1 H-pyrrole, 1 ,2-oxazole, 1 ,3-oxazole, 1 ,2-thiazole, 1 ,3-thiazole, imidazole, 1 H-pyrazole); more preferably heteroatoms are selected from O and S; most preferred heteroatom is O; also most preferred heteroatom is S;
- Y is 5-membered partially unsaturated carbocycle comprising 1 or 2 oxygen atoms
- Y is 6-membered partially or fully unsaturated carbocycle comprising 0, 1 , or 2 heteroatoms selected from O, N, and S;
- more preferred Y is 6-membered partially unsaturated carbocycle comprising 0, 1 , or 2 het- eroatoms selected from O, N, and S; more preferably heteroatoms are selected from O and S; also more preferably heteroatoms are selected from O and N; most preferred heteroatom is O; also more preferred Y is 6-membered fully unsaturated carbocycle comprising 0, 1 , or 2 heteroatoms N;
- R 3 is halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, or C3-C6-cycloal- kyl;
- R 3 is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy,
- R 3 is halogen, CN, Ci-C6-alkyl, or Ci-C6-alkoxy;
- R 3 is halogen
- R 3 is CI, Br, or I
- R 3 is CI or Br.
- R 3A is H, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl, C 3 -C 6 -alkenyl, C 3 -C 6 - haloalkenyl, C3-C6-alkenyl, C 3 -C6-haloalkenyl, or C 3 -C6-cycloalkyl;
- R 3A is H, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkylcarbonyl;
- R 3A is H, Ci-C6-alkyl, or Ci-C6-alkylcarbonyl
- R 3A is H, or Ci-C6-alkyl
- R 3A is H, or CH3.
- R 4 is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
- R 4 is halogen, Ci-C6-haloalkyl, or Ci-C6-alkyl;
- R 4 is halogen
- R 4 is Ci-C6-haloalkyl, or Ci-C6-alkyl
- R 4 is F, CI, CHF 2 , CF3, CH 3 , or C 2 H 5 ;
- R 4 is F
- R 4 is CH3
- R 4 is CI.
- R 4 is CF3.
- Preferred m is 0, 1 , or 2;
- m is 0 or 1 ;
- Preferred Z is A, B, C, D, E, F, G, H, I, J, or K;
- Z is A, E, or F
- Z is L, M, N, or O
- R 1 is preferably Ci-C6-alkyl, Ci-C6-alkoxy, or C3-C6-cycloalkyl, wherein the cycloalkyi substituent is unsubstituted;
- R 1 is C3-C6-cycloalkyl, wherein the cycloalkyi substituent is unsubstituted;
- R 2 is preferably C2-C6-alkenyl, C3-C6-cycloalkyl-Ci-C6-alkylidenyl, 5- or 6-membered het- eroaryl, Ci-C6-hydroxyalkyl, or C2-C6-dihydroxyalkyl;
- R 2 is C2-C6-alkenyl, 5- or 6-membered heteroaryl, or Ci-C6-hydroxyalkyl; also particularly preferred R 2 is C3-C6-cycloalkyl-CrC 6 -alkylidenyl, C2-C6-dihydroxyalkyl or 5- or 6-membered heteroaryl;
- R 2 is 2-furyl, 3-furyl, 2-methyl-3-furyl, 3-methyl-2-furyl, 4-methyloxazol-5- yl, CHOH-CHOH-C 6 H 5 , or CHOH-CHOH-2-furyl;
- A is preferably CR 3 , C * , N, O, S or NR 3A ;
- A is CR 3 , C * , or N;
- A is CR 3 , C * , O or S;
- Preferred Z is 9 or 10 membered bicyclic ring
- Z is 9 membered bicyclic ring
- Z is 10 membered bicyclic ring
- Z is selected from group A to O, as defined herein;
- R 3 is preferably halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
- R 3 is halogen or CH 3 ;
- R 3A is preferably H or Ci-C 6 -alkyl
- R 3A is H or CH3;
- m is preferably 0 or 1 ;
- R 4 is preferably halogen.
- R 2 is Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C 3 -C6-cycloalkyl-Ci-C6-alkyl, C 3 -C6-cycloal- kenyl-Ci-C6-alkyl, C 3 -C6-cycloalkyl-CrC 6 -alkylidenyl, Ci-C6-hydroxyalkyl, hydroxycarbonyl-Cr C6-alkyl, hydroxycarbonyl-Ci-C6-haloalkyl, Ci-C6-alkoxycarbonyl-Ci-C6-alkyl, Ci-C6-alkoxycar- bonyl-Ci-C6-haloalkyl, or 5- membered heteroaryl;
- cyclic groups of R 2 are unsubstituted or substituted by R c , and
- acyclic aliphatic groups of R 2 are unsubstituted or substituted by R d ;
- R b is d-Ce-alkyl
- R c is d-Ce-alkyl or OH
- R d is phenyl or 5- or 6- membered heteroaryl
- R d is unsubstituted or substituted by R e ;
- R e is halogen, CN, N0 2 , Ci-Ce-alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, Ci-C6-alkylsulfonyl;
- Z is A, E or F; Y is 5- or 6-membered partially unsaturated carbocycle comprising 1 or 2 oxygen atoms; R 3 is R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, or Ci-C6-haloalkoxy; prefer- rably Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-haloalkoxy; more preferrably CI, Br, F, I, CH3, or OCF3; most preferably CI;
- n 0 or 1 ;
- R 4 is halogen, preferably Br.
- R 1 is c-C 3 H 5 ;
- R 2 is Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C3-C6-cycloalkyl-Ci-C6-alkyl, d-Ce-cycloal- kenyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-alkylidenyl, Ci-C6-hydroxyalkyl, Ci-d-alkoxycarbonyl- Ci-C6-alkyl, or 5- membered heteroaryl;
- cyclic groups of R 2 are unsubstituted or substituted by R c , and
- acyclic aliphatic groups of R 2 are unsubstituted or substituted by R d ;
- R b is Ci-Ce-alkyl
- R c is Ci-Ce-alkyl or OH
- R d is 5- or 6- membered heteroaryl or 3- to 6-membered heterocyclyl
- R d is unsubstituted or substituted by R e ;
- R e is halogen, CN, N0 2 , Ci-Ce-alkyl, Ci-Ce-haloalkyl, OH, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, d-Ce-alkylsulfonyl;
- Y is 5- or 6-membered partially unsaturated carbocycle comprising 1 or 2 oxygen atoms;
- R 3 is R 3 is halogen, Ci-d-alkyl, Ci-d-haloalkyl, Ci-C6-alkoxy, or Ci-C6-haloalkoxy; preferably Ci-d-alkyl, Ci-C6-haloalkyl, or d-d-haloalkoxy; more preferably CI, Br, F, I, CH 3 , or OCF 3 ; most preferably CI;
- n is 0 or 1 ; preferably 0;
- R 4 is F, Br, CI, CHF 2 , CH 3 , CF 3 , or C2H5.
- R 2 is R 2 -9, R 2 -10 or R 2 -15, preferably R 2 -9;
- Y is 5- or 6-membered partially unsaturated carbocycle comprising 1 or 2 oxygen atoms;
- R 3 is R 3 is halogen, Ci-d-alkyl, Ci-d-haloalkyl, Ci-C6-alkoxy, or Ci-C6-haloalkoxy; preferably Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-d-haloalkoxy; more preferably CI, Br, F, I, CH3, or OCF3; most preferably CI;
- n is 0 or 1 ; preferably 0;
- R 4 is F, Br, CI, CHF 2 , CH 3 , CF 3 , or C2H5.
- dotted line ( ) is a single bond or a double bond
- R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
- A is CR 3 , C * , NR 3A , N, O or S;
- R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
- R 3A is H or Ci-Ce-alkyl
- Z is radical selected from A to O
- n 0 or 1 ;
- R 4 is F, CHF2, CF 3 , CH 3 , or C 2 H 5 .
- pyridine compounds of formula (1.2) corresponds to pyridine compounds of form and their use as herbicide
- dotted line ( ) is a single bond or a double bond
- R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
- A is CR 3 , C * , NR 3A , N, O or S;
- R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
- Z is radical selected from A to O
- n 0 or 1 ;
- R 4 is F, CHF 2 , CH3, CF 3 , or C 2 H 5 .
- pyridine compounds of formula (1.3) corresponds to pyridine compounds of form H2)4, and their use as herbicide,
- dotted line ( ) is a single bond or a double bond
- R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
- A is CR 3 , C * , NR 3A , N, O or S;
- R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
- Z is radical selected from A to O
- n 0 or 1 ;
- R 4 is F, CHF 2 , CH 3 , CF 3 , or C2H5.
- pyridine compounds of formula (1.4) corresponds to pyridine compounds of formula (I) wherein R 2 is 2-furyl
- their use as herbicide
- dotted line ( ) is a single bond or a double bond
- R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
- A is CR 3 , C * , NR 3A , N, O or S;
- R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
- Z is radical selected from A to O
- n 0 or 1 ;
- R 4 is F, CHF 2 , CH 3 , CF 3 , or C 2 H 5 .
- pyridine compounds of formula (1.5) corresponds to pyridine com- pounds of formula (I) wherein R 2 is 3-furyl
- their use as herbicide
- dotted line ( ) is a single bond or a double bond
- R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
- A is CR 3 , C * , NR 3A , N, O or S;
- R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
- Z is radical selected from A to O
- n 0 or 1 ;
- R 4 is F, CHF 2 , CH 3 , CF 3 , or C 2 H 5 .
- pyridine compounds of formula (1.6) corresponds to pyridine com- pounds of formula (I) wherein R 2 is 3-methyl-2-furyl
- their use as herbicide
- dotted line ( ) is a single bond or a double bond
- R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
- A is CR 3 , C * , NR 3A , N, O or S;
- R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
- Z is radical selected from A to O
- n 0 or 1 ;
- R 4 is F, CHF 2 , CH 3 , CF 3 , or C 2 H 5 .
- pyridine compounds of formula (1.7) corresponds to pyridine com- pounds of formula (I) wherein R 2 is 2-methyl-3-furyl
- their use as herbicide
- dotted line ( ) is a single bond or a double bond
- R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
- A is CR 3 , C * , NR 3A , N, O or S;
- R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
- Z is radical selected from A to O
- n 0 or 1 ;
- R 4 is F, CHF 2 , CH 3 , CF 3 , or C 2 H 5 .
- pyridine compounds of formula (1.8) corresponds to pyridine com- pounds of formul HOH-C6H5
- their use as herbicide are also preferred.
- dotted line ( ) is a single bond or a double bond
- R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
- A is CR 3 , C * , NR A , N, O or S;
- R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
- Z is radical selected from A to O
- n 0 or 1 ;
- R 4 is F, CHF 2 , CH 3 , CF 3 , or C2H5.
- pyridine compounds of formula (1.9) corresponds to pyridine pounds of formul HOH-2-furyl), and their use as herbicide,
- dotted line ( ) is a single bond or a double bond
- R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
- A is CR 3 , C * , NR A , N, O or S;
- R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
- Z is radical selected from A to O
- n 0 or 1 ;
- R 4 is F, CHF 2 , CH 3 , CF 3 , or C2H5. Also preferred are the pyridine compounds of formula (1.10) (corresponds to pyridine compounds of formula (I) wherein R 2 is 4-methyloxazol-5-yl, R 4 is H), and their use as herbicide,
- R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
- A is CR 3 , C * , NR 3A , N, O or S;
- R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
- Z is radical selected from A to O
- n 0 or 1 ;
- R 4 is F, CHF 2 , CH 3 , CF 3 , or C 2 H 5 .
- pyridine compounds of formula (1.1 1 ) corresponds to pyridin
- dotted line ( ) is a single bond or a double bond
- X 1 and Y 1 independently are selected from H, CH3, C2H5, n-propyl, iso-propyl, iso-butyl, n-bu- tyl, 2-butyl, t-butyl, OH, OCH 3 , SCH 3 , S(0)CH 3 , S(0) 2 CH 3 , CN, F, CI, Br, I, CH 2 CF 3 , CF 2 CF 3 , CF 2 CH 3 , CF 3 , CF 2 H, OCF 2 H, and OCF 3 ;
- R 1 is C 3 -C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy; preferably c-C 3 H5;
- A is CR 3 ;
- R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
- Z is radical selected from A to O
- n 0 or 1 ;
- R 4 is F, Br, CI, CHF 2 , CH 3 , CF 3 , or C 2 H 5 ; preferably F, CI, CHF 2 , CH 3 , CF 3 , or C 2 H 5 ; more preferably CI.
- pyridine compounds of formula (1.1 1) corresponds to pyridine compounds of formula (I), wherein R 2 is R 2 -9) and their use as herbicide,
- X 1 and Y 1 independently are selected from H, CH 3 , C2H5, n-propyl, iso-propyl, iso-butyl, n-bu- tyl, 2-butyl, t-butyl, OH, OCH 3 , SCH 3 , S(0)CH 3 , S(0) 2 CH 3 , CN, F, CI, Br, I, CH2CF3, CF2CF3, CF2CH3, CF 3 , CF2H, OCF2H, and OCF 3 ;
- X, V and W independently are CH 2 , CF 2 , O, NR 3A , N or S; wherein R 3A is H or CH 3 ;
- R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy; preferably C-C3H5;
- R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
- n 0 or 1 ;
- R 4 is F, Br, CI, CHF 2 , CH 3 , CF 3 , or C 2 H 5; preferably F, CI, CHF 2 , CH 3 , CF 3 , or C 2 H 5 ; more preferably CI.
- pyridine compounds of formula (1.1 1.C) corresponds to pyridine compounds of formula (I), wherein wherein R 2 is R 2 -9) and their use as herbicide,
- X 1 and Y 1 independently are selected from H, CH 3 , C2H5, n-propyl, iso-propyl, iso-butyl, n-bu- tyl, 2-butyl, t-butyl, OH, OCH 3 , SCH 3 , S(0)CH 3 , S(0) 2 CH 3 , CN, F, CI, Br, I, CH 2 CF 3 , CF 2 CF 3 , CF 2 CH 3 , CF 3 , CF 2 H, OCF 2 H, and OCF 3 ;
- X, V and W independently are CH 2 , CF 2 , O, NR 3A , N or S; wherein R 3A is H or CH 3 ;
- R 1 is C 3 -C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy; preferably c-C 3 Hs;
- R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
- n 0 or 1 ;
- R 4 is F, Br, CI, CHF 2 , CH 3 , CF 3 , or C 2 H 5; preferably F, CI, CHF 2 , CH 3 , CF 3 , or C 2 H 5 ; more preferably CI.
- pyridine compounds of formula I which corresponds to compounds of formulae I. a to I.I, and their use as herbicide, wherein X, V and W independently are CH 2 , CF 2 , O, NR A , N or S.
- pyridine compounds of formula I which corresponds to compounds of formulae l.m and l.n, and their use as herbicide, wherein X, and V independently are CH 2 , CF 2 , O, NR 3A , N or S, W independently is CH or N.
- R 1 is C2H5, C-C3H5, C-C4H7, or OCH3;
- R 3 is CH 3 , OCH3, CI, Br, CHF 2 , CF 3 , F, or I;
- V is CH 2 or CF 2 ;
- W is CH 2 , O, N, or S
- n 0 or 1 ;
- R 4 is F, CI or CF 3 .
- R 1 is C2H5, C-C3H5, C-C4H7, or OCH3;
- V is CH 2 or CF 2 ;
- W is CH or N
- n 0 or 1 ;
- R 4 is F, CI or CF 3 .
- Particularly preferred compounds of formula I, and their use as herbicide, compounds of the invention are the compounds of the formulae that are compiled in the following Tables 1 to 52.
- Compound 1.1 .1-3 e.g. comprises the compound of formula 1.1 from Table 1 and line I-3 from Table A;
- the pyridine compounds of formula (I) may be mixed with a large number of representatives of other herbicidal or growth- regulating active ingredient groups and then applied concomitantly.
- Suitable components for mixtures are, e.g., herbicides from the classes of the acetamides, amides,
- aryloxyphenoxypropionat.es benzamides, benzofuran, benzoic acids, benzothiadiazinones, bipyridylium, carbamates, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenol, diphenyl ether, glycines, imidazolinones, isoxazoles,
- phenylpyrazolines phenylpyridazines, phosphinic acids, phosphoroamidates,
- phosphorodithioates phthalamates, pyrazoles, pyridazinones, pyridines, pyridinecarboxylic acids, pyridinecarboxamides, pyrimidinediones, pyrimidinyl(thio)benzoates, quinolinecarboxylic acids, semicarbazones, sulfonylaminocarbonyltriazolinones, sulfonylureas, tetrazolinones, thiadiazoles, thiocarbamates, triazines, triazinones, triazoles, triazolinones,
- triazolocarboxamides triazolopyrimidines, triketones, uracils, or ureas.
- pyridine compounds of formula (I) alone or in combination with other herbicides, or else in the form of a mixture with other crop protection agents, e.g. together with agents for controlling pests or phytopathogenic fungi or bacteria.
- other crop protection agents e.g. together with agents for controlling pests or phytopathogenic fungi or bacteria.
- miscibility with mineral salt solutions which are employed for treating nutritional and trace element deficiencies.
- Other additives such as non-phytotoxic oils and oil concentrates may also be added.
- compositions according to the present invention comprise at least one pyridine compound of formula (I) (compound A) and at least one further active compound selected from herbicides B, preferably herbicides B of class b1 ) to b15), and safeners C (compound C).
- the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (1.1 ) (corresponds to pyridine compound of formula (I)), as defined herein;
- the composition comprises as active com- pound A or component A at least one, preferably exactly one, pyridine compound of formula (I.2) (corresponds to pyridine compound of formula (I)), as defined herein;
- the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (1.3) (corresponds to pyridine compound of formula (I)), as defined herein;
- the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (I.4) (corresponds to pyridine compound of formula (I)), as defined herein;
- the composition comprises as active com- pound A or component A at least one, preferably exactly one, pyridine compound of formula (1.5) (corresponds to pyridine compound of formula (I)), as defined herein;
- the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of for- mula (1.6) (corresponds to pyridine compound of formula (I)), as defined herein;
- the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (1.7) (corresponds to pyridine compound of formula (I)), as defined herein;
- the composition comprises as active com- pound A or component A at least one, preferably exactly one, pyridine compound of formula (1.8) (corresponds to pyridine compound of formula (I)), as defined herein;
- the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (1.9) (corresponds to pyridine compound of formula (I)), as defined herein;
- the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (1.10) (corresponds to pyridine compound of formula (I)), as defined herein;
- Preferred compounds of the formula (I) which, as component A, are constituent of the composition according to the invention are the compounds 1.1 to 1.10, as defined above;
- the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (1.1 1 ) (corresponds to pyridine compound of formula (I)), as defined herein;
- the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of for- mula (1.1 1.
- A) corresponds to pyridine compound of formula (I)), as defined herein;
- the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (1.1 1.C) (corresponds to pyridine compound of formula (I)), as defined herein;
- compositions according to the present invention comprise at least one pyridine compound of formula (I) and at least one further active compound B (herbicide B).
- the further herbicidal compound B (component B) is preferably selected from the herbicides of class b1 ) to b15):
- compositions can be selected from below herbicides B as defined below:
- ALS inhibitors acetolactate synthase inhibitors
- PPO inhibitors protoporphyrinogen-IX oxidase inhibitors
- EBP inhibitors enolpyruvyl shikimate 3-phosphate synthase inhibitors
- DHP inhibitors 7,8-dihydropteroate synthase inhibitors
- VLCFA inhibitors inhibitors of the synthesis of very long chain fatty acids
- herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat- metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flam- prop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol- butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dym- ron, methyl iodide,
- the compositions contain at least one inhibitor of the lipid biosynthesis (herbicide b1 ). These compounds inhibit lipid biosynthesis. Inhibition of the lipid bi- osynthesis can be affected either through inhibition of acetylCoA carboxylase (hereinafter- termed ACCase herbicides) or through a different mode of action (hereinafter termed non-AC- Case herbicides).
- ACCase herbicides belong to the group A of the HRAC classification system whereas the non-ACCase herbicides belong to the group N of the HRAC classification.
- the compositions contain at least one ALS inhibitor (herbicide b2). The herbicidal activity of these compounds is based on the inhibition of acetolac- tate synthase and thus on the inhibition of the branched chain amino acid biosynthesis. These inhibitors belong to the group B of the HRAC classification system.
- the compositions contain at least one inhibitor of photosynthesis (herbicide b3).
- the herbicidal activity of these compounds is based either on the in- hibition of the photosystem II in plants (so-called PSIl inhibitors, groups C1 , C2 and C3 of HRAC classification) or on diverting the electron transfer in photosystem I in plants (so-called PSI inhibitors, group D of HRAC classification) and thus on an inhibition of photosynthesis.
- PSIl inhibitors are preferred.
- compositions contain at least one inhibitor of pro- toporphyrinogen-IX-oxidase (herbicide b4).
- the herbicidal activity of these compounds is based on the inhibition of the protoporphyrinogen-IX-oxidase.
- These inhibitors belong to the group E of the HRAC classification system.
- the compositions contain at least one bleacher-herbicide (herbicide b5).
- the herbicidal activity of these compounds is based on the inhibition of the carotenoid biosynthesis.
- These include compounds which inhibit carotenoid biosynthesis by inhibition of phytoene desaturase (so-called PDS inhibitors, group F1 of HRAC classification), compounds that inhibit the 4-hydroxyphenylpyruvate-dioxygenase (HPPD inhibitors, group F2 of HRAC classification), compounds that inhibit DOXsynthase (group F4 of HRAC class) and compounds which inhibit carotenoid biosynthesis by an unknown mode of action (bleacher - unknown target, group F3 of HRAC classification).
- PDS inhibitors group F1 of HRAC classification
- HPPD inhibitors 4-hydroxyphenylpyruvate-dioxygenase
- DOXsynthase group F4 of HRAC class
- compounds which inhibit carotenoid biosynthesis by an unknown mode of action (bleacher -
- compositions contain at least one EPSP synthase inhibitor (herbicide b6).
- EPSP synthase inhibitor herebicide b6
- the herbicidal activity of these compounds is based on the inhibition of enolpyruvyl shikimate 3-phosphate synthase, and thus on the inhibition of the amino acid biosynthesis in plants.
- These inhibitors belong to the group G of the HRAC classification system.
- compositions contain at least one glutamine synthetase inhibitor (herbicide b7).
- the herbicidal activity of these compounds is based on the inhi- bition of glutamine synthetase, and thus on the inhibition of the aminoacid biosynthesis in plants.
- These inhibitors belong to the group H of the HRAC classification system.
- compositions contain at least one DHP synthase inhibitor (herbicide b8).
- DHP synthase inhibitor herebicide b8
- the herbicidal activity of these compounds is based on the inhibition of 7,8-dihydropteroate synthase.
- These inhibitors belong to the group I of the HRAC classification system.
- the compositions contain at least one mitosis inhibitor (herbicide b9).
- the herbicidal activity of these compounds is based on the disturbance or inhibition of microtubule formation or organization, and thus on the inhibition of mitosis.
- These inhibitors belong to the groups K1 and K2 of the HRAC classification system. Among these, com- pounds of the group K1 , in particular dinitroanilines, are preferred.
- the compositions contain at least one VLCFA inhibitor (herbicide b10).
- the herbicidal activity of these compounds is based on the inhibition of the synthesis of very long chain fatty acids and thus on the disturbance or inhibition of cell division in plants.
- These inhibitors belong to the group K3 of the HRAC classification system.
- the compositions contain at least one cellulose biosynthesis inhibitor (herbicide b1 1 ).
- the herbicidal activity of these compounds is based on the inhibition of the biosynthesis of cellulose and thus on the inhibition of the synthesis of cell walls in plants.
- These inhibitors belong to the group L of the HRAC classification system.
- compositions contain at least one decoupler herbi- cide (herbicide b12).
- the herbicidal activity of these compounds is based on the disruption of the cell membrane.
- These inhibitors belong to the group M of the HRAC classification system.
- the compositions contain at least one auxinic herbicide (herbicide b13).
- auxinic herbicide include compounds that mimic auxins, i.e. plant hormones, and affect the growth of the plants. These compounds belong to the group O of the HRAC classifica- tion system.
- compositions contain at least one auxin transport inhibitor (herbicide b14).
- auxin transport inhibitor hereinicide b14
- the herbicidal activity of these compounds is based on the inhibition of the auxin transport in plants.
- These compounds belong to the group P of the HRAC classification system.
- compositions according to the present invention comprising at least one herbicide B selected from herbicides of class b1 , b2, b3, b4, b5, b6, b9, b10, b13, and b14.
- compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b1 , b2, b4, b5, b9, b10, b13, and b14.
- compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b1 , b2, b4, b5, b9, b10, and b13
- herbicides B which can be used in combination with the compound of formula (I) according to the present invention are:
- ACC-herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxa- prop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pi- noxaden, profoxydim, propaquizafop, quizalofop, quizalofop-
- sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlo- rimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsul- furon-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosul- furon, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, met- azosulfuron, metsulfuron, met-
- imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, ima- zapyr, imazaquin and imazethapyr, triazolopyrimidine herbicides and sulfonanilides such as cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsu- lam, pyrimisulfan and pyroxsulam,
- pyrimidinylbenzoates such as bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyrimino- bac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidi- nyl)oxy]phenyl]methyl]amino]-benzoic acid-1-methylethyl ester (CAS 420138-41 -6), 4-[[[2-[(4,6- dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid propyl ester (CAS 420138-40- 5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-40- 5), N-(4-bromophenyl)-2-[(4,
- sulfonylaminocarbonyl-triazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl; and triafamone;
- compositions comprising at least one imidazolinone herbicide
- inhibitors of the photosystem II e.g. 1 -(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4- methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy- 4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1 -(5-tert-butylisoxazol-3-yl)-4-chloro- 2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1 ), 1-(5-tert-butyl-1 -methyl-pyrazol-3-yl)- 4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1 -methyl-py- razol-3-yl)-3-chloro-2-hydroxy-4-methyl
- a preferred embodiment of the invention relates to those compositions comprising at least one aryl urea herbicide. Among these, likewise a preferred embodiment of the invention relates to those compositions comprising at least one triazine herbicide. Among these, likewise a preferred embodiment of the invention relates to those compositions comprising at least one nitrile herbicide;
- acifluorfen acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluorogly- cofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyradonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulf
- PDS inhibitors beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS NOS NOS NOS NOS NOS NOS
- HPPD inhibitors benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21 -3), pyrasulfotole, pyrazol- ynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone , bleacher, unknown target: aclonifen, amitrole flumeturon,2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5- yl)-4-(trifluoromethyl)benzamide (CAS 1361 139-71 -0), 2-(2,4-dichlorophenyl)methyl-4,4-dime- thyl-3-isoxazolidone (CAS 81777-95-9) and 2-(2,5-d
- bilanaphos biases
- bilanaphos biases
- bilanaphos- sodium bilanaphos- sodium, glufosinate, glufosinate-P and glufosinate-ammonium
- compounds of group K1 dinitroanilines such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates such as ami- prophos, amiprophos-methyl, and butamiphos, benzoic acid herbicides such as chlorthal, chlor- thal-dimethyl, pyridines such as dithiopyr and thiazopyr, benzamides such as propyzamide and tebutam; compounds of group K2: carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and propham ; among these, compounds of group K1 , in particular dinitroanilines are preferred;
- chloroacetamides such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethe- namid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor, oxyacetanilides such as flufenacet and mefenacet, ac- etanilides such as diphenamid, naproanilide, napropamide and napropamide-M, tetrazolinones such fentrazamide, and other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfen- carbazone, piperophos, pyroxasulfone and isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8
- isoxazoline compounds are known in the art, e.g. from WO 2006/024820, WO
- chloroacetamides and oxyacetamides preference is given to chloroacetamides and oxyacetamides; b1 1 ) from the group of the cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1 -cyclohexyl-5-pentafluorphenyloxy-1 4 - [1 ,2,4,6]thiatriazin-3-ylamine (CAS 175899-01 -1 );
- 2,4-D and its salts and esters such as clacyfos, 2,4-DB and its salts and esters, aminocyclopy- rachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammo- nium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxifen, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethyl
- auxin transport inhibitors diflufenzopyr, diflufenzopyr-sodium, nap- talam and naptalam-sodium;
- Preferred herbicides B that can be used in combination with the pyridine compounds of the formula (I) according to the present invention are:
- ALS inhibitors amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac-sodium, chlorimuron-ethyl, chlor- sulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysul- furon, flazasulfuron, florasulam, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfu- ron-methyl-sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl- sodium, iofensulfuron, iofens
- acifluorfen-sodium bencarbazone, benzfendizone, butafenacil, carfentrazone-ethyl, cinidon- ethyl, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fomesafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, pyraflufen, pyraflufen-ethyl, saflufenacil, sul- fentrazone, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1 -methyl-6-trifluoromethyl- 2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyr
- glyphosate glyphosate, glyphosate-isopropylammonium, glyphosate-potassium and glyphosate-trimesium (sulfosate);
- glufosinate glufosinate-P, glufosinate-ammonium
- VLCFA inhibitors from the group of the VLCFA inhibitors: acetochlor, alachlor, amidochlor, anilofos, buta- chlor, cafenstrole, dimethenamid, dimethenamid-P, fentrazamide, flufenacet, mefenacet, meta- zachlor, metolachlor, S-metolachlor, naproanilide, napropamide, napropamide-M, pretilachlor, fenoxasulfone, ipfencarbazone, pyroxasulfone thenylchlor and isoxazoline-compounds of the formulae 11.1 , II.2, 11.3 , II.4, II.5, II.6, II.7, II.8 and II.9 as mentioned above;
- b1 1 from the group of the cellulose biosynthesis inhibitors: dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1-cyclohexyl-5-pentafluorphenyloxy-1 4 -[1 ,2,4,6]thiatriazin-3-ylamine (CAS 175899-01 -1 );
- 2,4-D and its salts and esters aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammoni- um and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, dichlor- prop-P and its salts and esters, flopyrauxifen, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8), MCPA and its salts and esters, MCPB and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661 -72-9) and 4-amino-3-chloro-5-
- auxin transport inhibitors diflufenzopyr and diflufenzopyr-sodium
- herbicides B that can be used in combination with the pyridine compounds of the formula (I) according to the present invention are: b1 ) from the group of the lipid biosynthesis inhibitors: clodinafop-propargyl, cycloxydim, cyha- lofop-butyl, fenoxaprop-P-ethyl, pinoxaden, profoxydim, tepraloxydim, tralkoxydim, 4-(4'-Chloro-
- ALS inhibitors from the group of the ALS inhibitors: bensulfuron-methyl, bispyribac-sodium, cyclosulfamu- ron, diclosulam, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imaza- pic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodi- um, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, nicosulfuron, penoxsu- lam, propoxycarbazon-sodium, propyrisulfuron, pyrazosulfuron-ethyl, pyroxsulam, rimsulfuron, sulfosulfuron, thiencarbazon
- b3 from the group of the photosynthesis inhibitors: ametryn, atrazine, diuron, fluometuron, hexazinone, isoproturon, linuron, metribuzin, paraquat, paraquat-dichloride, propanil, terbutryn, terbuthylazine, 1 -(5-tert-butylisoxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1 ), 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2- one (CAS 1844836-64-1 );
- glufosinate from the group of the glutamine synthase inhibitors: glufosinate, glufosinate-P and glufosinate-ammonium;
- VLCFA inhibitors from the group of the VLCFA inhibitors: acetochlor, cafenstrole, dimethenamid-P, fentra- zamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, fenoxasulfone, ipfen- carbazone and pyroxasulfone; likewise, preference is given to isoxazoline compounds of the formulae 11.1 , II.2, 11.3 , II.4, II.5, II.6, II.7, II.8 and II.9 as mentioned above;
- auxinic herbicides 2,4-D and its salts and esters such as clacyfos, and aminocyclopyrachlor and its salts and esters, aminopyralid and its salts and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, flopyrauxifen, fluroxypyr- meptyl, halauxifen, halauxifen-methyl, quinclorac, quinmerac, florpyrauxifen, florpyrauxifen-ben- zyl (CAS 1390661 -72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)picolinic acid (CAS 1629965-65-6);
- auxin transport inhibitors diflufenzopyr and diflufenzopyr-sodium
- herbicides B are the herbicides B as defined above; in particular, the herbicides B.1 - B.202 listed below in table B:
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Abstract
La présente invention concerne des composés de pyridine de la formule (I), ou leurs sels ou dérivés acceptables en agriculture en tant qu'herbicides, où les variables étant définies selon la description, l'utilisation des composés de pyridine de la formule (I) comme des herbicides, des compositions les contenant et leur utilisation en tant qu'herbicides, c'est-à-dire pour lutter contre les plantes nocives, et également une méthode de lutte contre une végétation indésirable consistant à laisser agir une quantité efficace d'herbicide d'au moins un composé de pyridine de la formule (I) pour agir sur les plantes, leurs graines et/ou leur habitat.
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10863743B2 (en) | 2016-07-29 | 2020-12-15 | Basf Se | Method for controlling PPO resistant weeds |
US11185075B2 (en) | 2016-12-16 | 2021-11-30 | Basf Se | Herbicidal phenyltriazolinones |
US11292784B2 (en) | 2017-11-27 | 2022-04-05 | Basf Se | Crystalline forms of ethyl 2-[[3-[[3- chloro-5-fluoro-6-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-2-pyridyl]oxy] acetate |
US12133529B2 (en) | 2017-11-23 | 2024-11-05 | Basf Se | Herbicidal phenylethers |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10863743B2 (en) | 2016-07-29 | 2020-12-15 | Basf Se | Method for controlling PPO resistant weeds |
US11419337B2 (en) | 2016-07-29 | 2022-08-23 | Basf Se | Method for controlling PPO resistant weeds |
US11766044B2 (en) | 2016-07-29 | 2023-09-26 | Basf Se | Method for controlling PPO resistant weeds |
US11185075B2 (en) | 2016-12-16 | 2021-11-30 | Basf Se | Herbicidal phenyltriazolinones |
US12133529B2 (en) | 2017-11-23 | 2024-11-05 | Basf Se | Herbicidal phenylethers |
US11292784B2 (en) | 2017-11-27 | 2022-04-05 | Basf Se | Crystalline forms of ethyl 2-[[3-[[3- chloro-5-fluoro-6-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-2-pyridyl]oxy] acetate |
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