CA2956302A1 - Bicyclic arylcarboxylic acid amides and their use as herbicides - Google Patents
Bicyclic arylcarboxylic acid amides and their use as herbicides Download PDFInfo
- Publication number
- CA2956302A1 CA2956302A1 CA2956302A CA2956302A CA2956302A1 CA 2956302 A1 CA2956302 A1 CA 2956302A1 CA 2956302 A CA2956302 A CA 2956302A CA 2956302 A CA2956302 A CA 2956302A CA 2956302 A1 CA2956302 A1 CA 2956302A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- cycloalkyl
- alkoxy
- halo
- radicals
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000004009 herbicide Substances 0.000 title claims abstract description 20
- 125000002619 bicyclic group Chemical group 0.000 title claims abstract description 11
- 150000001408 amides Chemical class 0.000 title abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 85
- 150000002367 halogens Chemical class 0.000 claims abstract description 85
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 55
- 239000001257 hydrogen Substances 0.000 claims abstract description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 44
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 31
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 21
- 150000001721 carbon Chemical group 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 7
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract 26
- -1 cyano, formyl Chemical group 0.000 claims description 199
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 181
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 36
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 30
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 30
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 28
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 239000001301 oxygen Substances 0.000 claims description 28
- 125000004043 oxo group Chemical group O=* 0.000 claims description 26
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 25
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 230000009261 transgenic effect Effects 0.000 claims description 21
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 238000009472 formulation Methods 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 230000002363 herbicidal effect Effects 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 11
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 10
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 8
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 8
- GRHZLQBPAJAHDM-SPRQWYLLSA-N [(3as,4r,6ar)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] n-[(2s,4s,5s)-5-[[2-(2,6-dimethylphenoxy)acetyl]amino]-4-hydroxy-1,6-diphenylhexan-2-yl]carbamate Chemical compound CC1=CC=CC(C)=C1OCC(=O)N[C@H]([C@@H](O)C[C@H](CC=1C=CC=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)CC1=CC=CC=C1 GRHZLQBPAJAHDM-SPRQWYLLSA-N 0.000 claims description 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 6
- 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 claims description 6
- HCUOEKSZWPGJIM-YBRHCDHNSA-N (e,2e)-2-hydroxyimino-6-methoxy-4-methyl-5-nitrohex-3-enamide Chemical compound COCC([N+]([O-])=O)\C(C)=C\C(=N/O)\C(N)=O HCUOEKSZWPGJIM-YBRHCDHNSA-N 0.000 claims description 6
- 101100496169 Arabidopsis thaliana CLH1 gene Proteins 0.000 claims description 6
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 6
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 6
- 101001109689 Homo sapiens Nuclear receptor subfamily 4 group A member 3 Proteins 0.000 claims description 6
- 101000598778 Homo sapiens Protein OSCP1 Proteins 0.000 claims description 6
- 101100044057 Mesocricetus auratus SYCP3 gene Proteins 0.000 claims description 6
- 101001067395 Mus musculus Phospholipid scramblase 1 Proteins 0.000 claims description 6
- 102100022673 Nuclear receptor subfamily 4 group A member 3 Human genes 0.000 claims description 6
- 101100080600 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nse6 gene Proteins 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 101150111293 cor-1 gene Proteins 0.000 claims description 6
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 6
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 5
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 4
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 4
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 4
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 4
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- 239000011737 fluorine Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000003630 growth substance Substances 0.000 claims description 3
- 239000002917 insecticide Substances 0.000 claims description 3
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 2
- 102000034570 NR1 subfamily Human genes 0.000 claims description 2
- 108020001305 NR1 subfamily Proteins 0.000 claims description 2
- 230000000895 acaricidal effect Effects 0.000 claims description 2
- 239000000642 acaricide Substances 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- OAWUUPVZMNKZRY-UHFFFAOYSA-N cyprosulfamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NC2CC2)C=C1 OAWUUPVZMNKZRY-UHFFFAOYSA-N 0.000 claims description 2
- OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical group CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 claims description 2
- 239000000417 fungicide Substances 0.000 claims description 2
- COYBRKAVBMYYSF-UHFFFAOYSA-N heptan-2-yl [(5-chloroquinolin-8-yl)oxy]acetate Chemical group C1=CN=C2C(OCC(=O)OC(C)CCCCC)=CC=C(Cl)C2=C1 COYBRKAVBMYYSF-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- MWKVXOJATACCCH-UHFFFAOYSA-N isoxadifen-ethyl Chemical group C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 claims description 2
- 125000006557 (C2-C5) alkylene group Chemical group 0.000 claims 7
- 244000045561 useful plants Species 0.000 claims 3
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- 239000000460 chlorine Substances 0.000 description 102
- 241000196324 Embryophyta Species 0.000 description 69
- 150000001875 compounds Chemical class 0.000 description 51
- 150000003254 radicals Chemical class 0.000 description 48
- 239000004480 active ingredient Substances 0.000 description 20
- 244000038559 crop plants Species 0.000 description 20
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
- 108090000623 proteins and genes Proteins 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000008187 granular material Substances 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000843 powder Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 239000004495 emulsifiable concentrate Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000004562 water dispersible granule Substances 0.000 description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
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- 238000000227 grinding Methods 0.000 description 5
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- ZXYUYVATXKYRBC-UHFFFAOYSA-N 3-chloro-4-methylsulfanyl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid Chemical compound ClC=1C(=CC=2CCCCC=2C=1SC)C(=O)O ZXYUYVATXKYRBC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- 108091028043 Nucleic acid sequence Proteins 0.000 description 3
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- 150000001412 amines Chemical class 0.000 description 3
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- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
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- NPONDHXJAVTEEO-UHFFFAOYSA-N methyl 3-amino-5,6,7,8-tetrahydronaphthalene-2-carboxylate Chemical compound C1CCCC2=C1C=C(C(=O)OC)C(N)=C2 NPONDHXJAVTEEO-UHFFFAOYSA-N 0.000 description 1
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- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical group ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
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- 235000005985 organic acids Nutrition 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
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- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
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- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 230000005097 photorespiration Effects 0.000 description 1
- 239000000280 phytoalexin Substances 0.000 description 1
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- 230000000885 phytotoxic effect Effects 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 239000002675 polymer-supported reagent Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 230000032361 posttranscriptional gene silencing Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- 125000003373 pyrazinyl group Chemical group 0.000 description 1
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- 125000002098 pyridazinyl group Chemical group 0.000 description 1
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- 239000010453 quartz Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
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- 108091092562 ribozyme Proteins 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 229940079101 sodium sulfide Drugs 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- ZGHLCBJZQLNUAZ-UHFFFAOYSA-N sodium sulfide nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[Na+].[S-2] ZGHLCBJZQLNUAZ-UHFFFAOYSA-N 0.000 description 1
- 229940048181 sodium sulfide nonahydrate Drugs 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- WMDLZMCDBSJMTM-UHFFFAOYSA-M sodium;sulfanide;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[SH-] WMDLZMCDBSJMTM-UHFFFAOYSA-M 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
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- 230000003068 static effect Effects 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
- 230000036435 stunted growth Effects 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
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- 150000007944 thiolates Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
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- 239000001993 wax Substances 0.000 description 1
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- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
-
- 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
- A01N43/82—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 three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/08—1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—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
- 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
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—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
- C07D409/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14178795 | 2014-07-28 | ||
| EP14178795.2 | 2014-07-28 | ||
| PCT/EP2015/066955 WO2016016107A1 (de) | 2014-07-28 | 2015-07-24 | Bicyclische arylcarbonsäureamide und ihre verwendung als herbizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2956302A1 true CA2956302A1 (en) | 2016-02-04 |
Family
ID=51292804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2956302A Abandoned CA2956302A1 (en) | 2014-07-28 | 2015-07-24 | Bicyclic arylcarboxylic acid amides and their use as herbicides |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9914710B2 (OSRAM) |
| EP (1) | EP3174871B1 (OSRAM) |
| JP (1) | JP6643315B2 (OSRAM) |
| CN (1) | CN106715403B (OSRAM) |
| AR (1) | AR101230A1 (OSRAM) |
| AU (1) | AU2015295590A1 (OSRAM) |
| BR (1) | BR112017001433B1 (OSRAM) |
| CA (1) | CA2956302A1 (OSRAM) |
| EA (1) | EA201790281A1 (OSRAM) |
| MX (1) | MX2017001320A (OSRAM) |
| WO (1) | WO2016016107A1 (OSRAM) |
| ZA (1) | ZA201700704B (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018114663A1 (de) | 2016-12-22 | 2018-06-28 | Bayer Cropscience Aktiengesellschaft | Substituierte azolylpyrrolone und azolylhydantoine sowie deren salze und ihre verwendung als herbizide wirkstoffe |
| US20200196601A1 (en) * | 2017-05-04 | 2020-06-25 | Bayer Cropscience Aktiengesellschaft | Herbicide safener compositions containing quinazolinedione-6carbonyl derivatives |
| BR112020017575A2 (pt) * | 2018-02-28 | 2020-12-22 | Bayer Aktiengesellschaft | Benzamidas bicíclicas herbicidamente ativas |
| CN110669016B (zh) * | 2018-09-29 | 2021-05-25 | 山东先达农化股份有限公司 | 三酮类化合物及其制备方法和应用以及一种除草剂 |
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| JPS4924073B2 (OSRAM) * | 1971-06-12 | 1974-06-20 | Adeka Argus Chemical Co Ltd | |
| CN1153515A (zh) * | 1994-06-10 | 1997-07-02 | 拜尔公司 | N-杂环基-杂芳氧基乙酰胺 |
| EP1101758A4 (en) * | 1998-07-28 | 2002-04-03 | Nihon Nohyaku Co Ltd | CONDENSED HETEROCYCLIC DICARBONIC ACID DIAMOND DERIVATIVES OR SALTS THEREOF, HERBICIDES AND THEIR USE |
| DK2611785T3 (da) * | 2010-09-01 | 2014-08-25 | Bayer Ip Gmbh | N-(tetrazol-5yl)- og n- (triazol-5-yl) arylcarboxylsyreamider og deres anvendelse som herbicider |
| EA023169B1 (ru) * | 2011-03-15 | 2016-04-29 | Байер Интеллектуэль Проперти Гмбх | Амиды n-(1,2,5-оксадиазол-3-ил)-, n-(тетразол-5-ил)- и n-(триазол-5-ил)бициклоарилкарбоновых кислот и гербицидные средства |
| PT2688885T (pt) * | 2011-03-22 | 2016-09-06 | Bayer Ip Gmbh | Amidas de ácido n-(1,3,4-oxadiazol-2-il)-arilcarboxílico e a utilização das mesmas como herbicidas |
| EP2589598A1 (de) * | 2011-11-03 | 2013-05-08 | Bayer CropScience AG | 5-Phenylsubstituierte N-(Tetrazol-5-yl)- und N-(Triazol-5-yl)arylcarbonsäureamide und ihre Verwendung als Herbizide |
| AU2012338879A1 (en) * | 2011-11-16 | 2014-06-05 | Basf Se | Substituted 1,2,5-oxadiazole compounds and their use as herbicides II |
| WO2013072450A1 (en) * | 2011-11-18 | 2013-05-23 | Basf Se | Substituted 1,2,5-oxadiazole compounds and their use as herbicides iii |
| PL2793589T3 (pl) * | 2011-12-21 | 2018-05-30 | Syngenta Limited | Związki herbicydowe |
| BR112014026823A2 (pt) * | 2012-04-27 | 2017-06-27 | Basf Se | compostos de n-(tetrazol-5-il) e n-(triazol-5-il)arilcarboxamida substituída e seu uso como herbicidas. |
| US20150216171A1 (en) * | 2012-09-05 | 2015-08-06 | Bayer Cropscience Ag | Herbicidally active bicycloaryl carboxylic acid amides |
| WO2014086737A1 (de) * | 2012-12-06 | 2014-06-12 | Bayer Cropscience Ag | Kondensierte 2-pyridon-3-carboxamide und ihre verwendung als herbizide |
| WO2014086746A1 (de) * | 2012-12-07 | 2014-06-12 | Bayer Cropscience Ag | N-(isoxazol-3-yl)-arylcarbonsäureamide und ihre verwendung als herbizide |
-
2015
- 2015-07-17 AR ARP150102275A patent/AR101230A1/es unknown
- 2015-07-24 EP EP15738948.7A patent/EP3174871B1/de active Active
- 2015-07-24 BR BR112017001433-5A patent/BR112017001433B1/pt active IP Right Grant
- 2015-07-24 CA CA2956302A patent/CA2956302A1/en not_active Abandoned
- 2015-07-24 MX MX2017001320A patent/MX2017001320A/es unknown
- 2015-07-24 US US15/328,253 patent/US9914710B2/en active Active
- 2015-07-24 CN CN201580051066.6A patent/CN106715403B/zh active Active
- 2015-07-24 JP JP2017504417A patent/JP6643315B2/ja active Active
- 2015-07-24 AU AU2015295590A patent/AU2015295590A1/en not_active Abandoned
- 2015-07-24 EA EA201790281A patent/EA201790281A1/ru unknown
- 2015-07-24 WO PCT/EP2015/066955 patent/WO2016016107A1/de not_active Ceased
-
2017
- 2017-01-27 ZA ZA2017/00704A patent/ZA201700704B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN106715403A (zh) | 2017-05-24 |
| JP2017523186A (ja) | 2017-08-17 |
| AU2015295590A1 (en) | 2017-02-16 |
| BR112017001433A2 (pt) | 2017-12-05 |
| EA201790281A1 (ru) | 2017-11-30 |
| AR101230A1 (es) | 2016-11-30 |
| JP6643315B2 (ja) | 2020-02-12 |
| US20170217909A1 (en) | 2017-08-03 |
| BR112017001433B1 (pt) | 2021-08-10 |
| CN106715403B (zh) | 2020-06-02 |
| WO2016016107A1 (de) | 2016-02-04 |
| ZA201700704B (en) | 2018-05-30 |
| MX2017001320A (es) | 2017-05-09 |
| EP3174871A1 (de) | 2017-06-07 |
| EP3174871B1 (de) | 2018-11-21 |
| US9914710B2 (en) | 2018-03-13 |
| AU2015295590A2 (en) | 2017-03-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20200831 |