ES2420533T3 - 2-(3-Alquiltiobenzoíl)ciclohexanodionas y su utilización como herbicidas - Google Patents
2-(3-Alquiltiobenzoíl)ciclohexanodionas y su utilización como herbicidas Download PDFInfo
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- ES2420533T3 ES2420533T3 ES10735211T ES10735211T ES2420533T3 ES 2420533 T3 ES2420533 T3 ES 2420533T3 ES 10735211 T ES10735211 T ES 10735211T ES 10735211 T ES10735211 T ES 10735211T ES 2420533 T3 ES2420533 T3 ES 2420533T3
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- alkyl
- hydrogen
- methyl
- ethyl
- plants
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- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical class O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 239000004009 herbicide Substances 0.000 title claims description 25
- 239000001257 hydrogen Substances 0.000 claims abstract description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 24
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 17
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 3
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims description 80
- 239000000203 mixture Substances 0.000 claims description 50
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 238000009472 formulation Methods 0.000 claims description 24
- 150000003254 radicals Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- 230000009261 transgenic effect Effects 0.000 claims description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 239000011593 sulfur Substances 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 230000002363 herbicidal effect Effects 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- 230000008635 plant growth Effects 0.000 claims description 5
- 244000045561 useful plants Species 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 244000038559 crop plants Species 0.000 claims description 3
- 230000001629 suppression Effects 0.000 claims description 3
- FKTXDTWDCPTPHK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical group FC(F)(F)[C](F)C(F)(F)F FKTXDTWDCPTPHK-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 85
- -1 alkyl radicals Chemical class 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 26
- 239000013543 active substance Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
- 239000000126 substance Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 15
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- 239000000843 powder Substances 0.000 description 13
- 230000000694 effects Effects 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 159000000000 sodium salts Chemical class 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 239000004562 water dispersible granule Substances 0.000 description 6
- XKLPBDMZJSWRBL-UHFFFAOYSA-N 3-benzoylcyclohexane-1,2-dione Chemical class C=1C=CC=CC=1C(=O)C1CCCC(=O)C1=O XKLPBDMZJSWRBL-UHFFFAOYSA-N 0.000 description 5
- 244000062793 Sorghum vulgare Species 0.000 description 5
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- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
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- 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 4
- 241000207783 Ipomoea Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 4
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- BCGWCDYXXVAANY-UHFFFAOYSA-N methyl 2-methoxy-3-methylsulfanyl-4-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(C(F)(F)F)C(SC)=C1OC BCGWCDYXXVAANY-UHFFFAOYSA-N 0.000 description 4
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- ONGMFZCVYSBZAT-UHFFFAOYSA-N (3-oxocyclohexen-1-yl) 2-methoxy-3-methylsulfanyl-4-(trifluoromethyl)benzoate Chemical compound COC1=C(SC)C(C(F)(F)F)=CC=C1C(=O)OC1=CC(=O)CCC1 ONGMFZCVYSBZAT-UHFFFAOYSA-N 0.000 description 3
- WHYOFKANDRDTLV-UHFFFAOYSA-N (3-oxocyclohexen-1-yl) 2-methoxy-3-methylsulfinyl-4-(trifluoromethyl)benzoate Chemical compound C1=CC(C(F)(F)F)=C(S(C)=O)C(OC)=C1C(=O)OC1=CC(=O)CCC1 WHYOFKANDRDTLV-UHFFFAOYSA-N 0.000 description 3
- YGOPNHNGSCJECX-UHFFFAOYSA-N 1-fluoro-2-methylsulfanyl-3-(trifluoromethyl)benzene Chemical compound CSC1=C(F)C=CC=C1C(F)(F)F YGOPNHNGSCJECX-UHFFFAOYSA-N 0.000 description 3
- YGQSKTBDWOJUKP-UHFFFAOYSA-N 2-[2-methoxy-3-methylsulfinyl-4-(trifluoromethyl)benzoyl]cyclohexane-1,3-dione Chemical compound C1=CC(C(F)(F)F)=C(S(C)=O)C(OC)=C1C(=O)C1C(=O)CCCC1=O YGQSKTBDWOJUKP-UHFFFAOYSA-N 0.000 description 3
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- 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 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
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- USSIUIGPBLPCDF-KEBDBYFISA-N pyriminobac-methyl Chemical group CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC USSIUIGPBLPCDF-KEBDBYFISA-N 0.000 description 1
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- RTWIRLHWLMNVCC-WQYNNSOESA-M sodium (2S)-2-[[(2S)-2-[[(2S)-2-amino-4-[hydroxy(methyl)phosphoryl]butanoyl]amino]propanoyl]amino]propanoate Chemical compound [Na+].[O-]C(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](N)CCP(C)(O)=O RTWIRLHWLMNVCC-WQYNNSOESA-M 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- DEWVPZYHFVYXMZ-QCILGFJPSA-M sodium;(3ar,4as,8ar,8bs)-2,2,7,7-tetramethyl-4a,5,8a,8b-tetrahydro-[1,3]dioxolo[3,4]furo[1,3-d][1,3]dioxine-3a-carboxylate Chemical compound [Na+].O([C@H]12)C(C)(C)OC[C@@H]1O[C@]1(C([O-])=O)[C@H]2OC(C)(C)O1 DEWVPZYHFVYXMZ-QCILGFJPSA-M 0.000 description 1
- AXKBOWBNOCUNJL-UHFFFAOYSA-M sodium;2-nitrophenolate Chemical compound [Na+].[O-]C1=CC=CC=C1[N+]([O-])=O AXKBOWBNOCUNJL-UHFFFAOYSA-M 0.000 description 1
- GABUSZPTCJGKGB-UHFFFAOYSA-M sodium;4-(4-chloro-2-methylphenoxy)butanoate Chemical compound [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
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- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
- FRGKKTITADJNOE-UHFFFAOYSA-N sulfanyloxyethane Chemical compound CCOS FRGKKTITADJNOE-UHFFFAOYSA-N 0.000 description 1
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 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
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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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- XSKZXGDFSCCXQX-UHFFFAOYSA-N thiencarbazone-methyl Chemical compound COC(=O)C1=CSC(C)=C1S(=O)(=O)NC(=O)N1C(=O)N(C)C(OC)=N1 XSKZXGDFSCCXQX-UHFFFAOYSA-N 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
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
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- 238000006177 thiolation reaction Methods 0.000 description 1
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
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- 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
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-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
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- YNWVFADWVLCOPU-MAUPQMMJSA-N uniconazole P Chemical compound C1=NC=NN1/C([C@@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MAUPQMMJSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catching Or Destruction (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22936509P | 2009-07-29 | 2009-07-29 | |
| DE102009009777 | 2009-07-29 | ||
| US229365P | 2009-07-29 | ||
| EP09009777 | 2009-07-29 | ||
| PCT/EP2010/004445 WO2011012247A1 (de) | 2009-07-29 | 2010-07-21 | 2-(3-alkylthiobenzoyl)cyclohexandione und ihre verwendung als herbizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2420533T3 true ES2420533T3 (es) | 2013-08-23 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10735211T Active ES2420533T3 (es) | 2009-07-29 | 2010-07-21 | 2-(3-Alquiltiobenzoíl)ciclohexanodionas y su utilización como herbicidas |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8193121B2 (enExample) |
| EP (1) | EP2459528B1 (enExample) |
| JP (1) | JP5795315B2 (enExample) |
| KR (1) | KR101767519B1 (enExample) |
| CN (1) | CN102548960A (enExample) |
| AR (1) | AR078083A1 (enExample) |
| AU (1) | AU2010278335A1 (enExample) |
| BR (1) | BR112012001940B1 (enExample) |
| CA (1) | CA2769451A1 (enExample) |
| DK (1) | DK2459528T3 (enExample) |
| EA (1) | EA201270089A1 (enExample) |
| ES (1) | ES2420533T3 (enExample) |
| IN (1) | IN2012DN00773A (enExample) |
| MX (1) | MX2012001155A (enExample) |
| WO (1) | WO2011012247A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2595955B1 (de) * | 2010-07-21 | 2016-11-30 | Bayer Intellectual Property GmbH | (4-halogenalkyl-3-thiobenzoyl)cyclohexandione und ihre verwendung als herbizide |
| US8563779B2 (en) | 2010-07-21 | 2013-10-22 | Bayer Cropscience Ag | (4-trifluoromethyl-3-thiobenzoyl)cyclohexanediones and use thereof as herbicides |
| US8455657B2 (en) | 2010-12-28 | 2013-06-04 | Bayer Cropscience Ag | Process for the preparation of 3-alkylsulfinylbenzoyl derivatives |
| EP2817296B1 (de) | 2012-02-21 | 2016-08-31 | Bayer Intellectual Property GmbH | Herbizid wirksame 3-(sulfin-/sulfonimidoyl)-benzamide |
| BR112014020601B1 (pt) | 2012-02-21 | 2019-05-28 | Bayer Intellectual Property Gmbh | Herbicidas derivados de sulfinimidoil- e sulfonimidoilbenzoíla, seu intermediário e seus usos, composição herbicida, e método para controle de plantas indesejadas |
| BR112015013186B1 (pt) * | 2012-12-14 | 2019-07-30 | Bayer Cropscience Ag | Processo para preparar derivados de ácido 2-hidroxibenzóico substituído de 4-haloalquil-3-mercapto. |
| CN111356368B (zh) * | 2017-11-20 | 2025-02-25 | 拜耳公司 | 除草活性的双环苯甲酰胺 |
| CN110590623B (zh) * | 2019-09-27 | 2022-04-19 | 江苏好收成韦恩农化股份有限公司 | 连续流微通道反应器中制备6-取代-2-三氟甲基苯丙硫醚的方法 |
| CN118344271A (zh) * | 2023-01-16 | 2024-07-16 | 沈阳万菱生物技术有限公司 | 烷氧基取代的苯甲酰氧代环己烯硫醚类化合物及其制备方法和应用 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4780127A (en) * | 1982-03-25 | 1988-10-25 | Stauffer Chemical Company | Certain 2-(substituted benzoyl)-1,3-cyclohexanediones and their use as herbicides |
| EP0131624B1 (en) | 1983-01-17 | 1992-09-16 | Monsanto Company | Plasmids for transforming plant cells |
| DE3474297D1 (en) | 1983-09-16 | 1988-11-03 | Stauffer Chemical Co | Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones |
| BR8404834A (pt) | 1983-09-26 | 1985-08-13 | Agrigenetics Res Ass | Metodo para modificar geneticamente uma celula vegetal |
| BR8600161A (pt) | 1985-01-18 | 1986-09-23 | Plant Genetic Systems Nv | Gene quimerico,vetores de plasmidio hibrido,intermediario,processo para controlar insetos em agricultura ou horticultura,composicao inseticida,processo para transformar celulas de plantas para expressar uma toxina de polipeptideo produzida por bacillus thuringiensis,planta,semente de planta,cultura de celulas e plasmidio |
| DE3686633T2 (de) | 1985-10-25 | 1993-04-15 | David Matthew Bisaro | Pflanzenvektoren. |
| ATE57390T1 (de) | 1986-03-11 | 1990-10-15 | Plant Genetic Systems Nv | Durch gentechnologie erhaltene und gegen glutaminsynthetase-inhibitoren resistente pflanzenzellen. |
| US4775411A (en) * | 1986-06-09 | 1988-10-04 | Stauffer Chemica Company | Certain substituted 3-amino-2-benzoylcyclohex-2-enones |
| US4762551A (en) | 1986-06-09 | 1988-08-09 | Stauffer Chemical Company | Certain 3-(substituted thio)-2-benzoyl-cyclohex-2-enones |
| US5013659A (en) | 1987-07-27 | 1991-05-07 | E. I. Du Pont De Nemours And Company | Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase |
| IL83348A (en) | 1986-08-26 | 1995-12-08 | Du Pont | Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase |
| CN87106999A (zh) * | 1986-10-16 | 1988-09-21 | 斯托弗化学公司 | 2-(2-取代苯甲酰基)-4-(取代)-1，3-环己烷二酮 |
| US4783213A (en) * | 1986-10-16 | 1988-11-08 | Stauffer Chemical Company | Certain 2-(2-substituted benzoyl)-4-(substituted oxy or substituted thio)-1,3-cyclohexanediones |
| HU206242B (en) * | 1988-04-18 | 1992-10-28 | Sandoz Ag | Herbicidal compositions comprising substituted benzoyl bicyclodione derivatives as active ingredient |
| DE69133261D1 (de) | 1990-03-16 | 2003-06-26 | Calgene Llc Davis | Dnas, die für pflanzliche desaturasen kodieren und deren anwendungen |
| RU2148081C1 (ru) | 1990-06-18 | 2000-04-27 | Монсанто Компани | Способ получения генетически трансформированных растений с повышенным содержанием крахмала и рекомбинантная двухцепочечная днк-молекула |
| ES2173077T3 (es) | 1990-06-25 | 2002-10-16 | Monsanto Technology Llc | Plantas que toleran glifosato. |
| SE467358B (sv) | 1990-12-21 | 1992-07-06 | Amylogene Hb | Genteknisk foeraendring av potatis foer bildning av staerkelse av amylopektintyp |
| DE4104782B4 (de) | 1991-02-13 | 2006-05-11 | Bayer Cropscience Gmbh | Neue Plasmide, enthaltend DNA-Sequenzen, die Veränderungen der Karbohydratkonzentration und Karbohydratzusammensetzung in Pflanzen hervorrufen, sowie Pflanzen und Pflanzenzellen enthaltend dieses Plasmide |
| EP0563817A3 (en) * | 1992-03-31 | 1993-11-03 | Hoechst Ag | Salts of 2-benzoyl-cyclohexane diones, selective herbicidal agents, process for their preparation and their use for combatting weeds |
| WO1997003045A1 (en) * | 1995-07-10 | 1997-01-30 | E.I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| CA2332348A1 (en) * | 1998-06-26 | 2000-01-06 | Novartis Ag | Herbicidal composition |
| JP2001122848A (ja) * | 1999-08-19 | 2001-05-08 | Ishihara Sangyo Kaisha Ltd | トリケトン系化合物、それらの製造方法及びそれらを含有する除草剤 |
| US7196229B2 (en) * | 2001-08-08 | 2007-03-27 | Basf Aktiengesellschaft | Benzoylcyclohexenone derivatives |
| DE10215723A1 (de) | 2002-04-10 | 2003-10-30 | Bayer Cropscience Gmbh | 3-Keto oder 3-Oximether substituierte Benzoylcyclohexandione |
| AR049448A1 (es) * | 2004-06-22 | 2006-08-02 | Syngenta Participations Ag | Biciclooctenos sustituidos y usos como herbicidas |
| MX2012001245A (es) * | 2009-07-29 | 2012-04-20 | Bayer Cropscience Ag | 4-(3-alquilbenzoil)pirazoles y su uso como herbicidas. |
-
2010
- 2010-07-21 IN IN773DEN2012 patent/IN2012DN00773A/en unknown
- 2010-07-21 WO PCT/EP2010/004445 patent/WO2011012247A1/de not_active Ceased
- 2010-07-21 MX MX2012001155A patent/MX2012001155A/es active IP Right Grant
- 2010-07-21 EA EA201270089A patent/EA201270089A1/ru unknown
- 2010-07-21 BR BR112012001940-6A patent/BR112012001940B1/pt active IP Right Grant
- 2010-07-21 CN CN2010800418775A patent/CN102548960A/zh active Pending
- 2010-07-21 CA CA2769451A patent/CA2769451A1/en not_active Abandoned
- 2010-07-21 AU AU2010278335A patent/AU2010278335A1/en not_active Abandoned
- 2010-07-21 ES ES10735211T patent/ES2420533T3/es active Active
- 2010-07-21 KR KR1020127005347A patent/KR101767519B1/ko active Active
- 2010-07-21 EP EP10735211.4A patent/EP2459528B1/de active Active
- 2010-07-21 DK DK10735211.4T patent/DK2459528T3/da active
- 2010-07-21 JP JP2012522006A patent/JP5795315B2/ja active Active
- 2010-07-27 AR ARP100102711A patent/AR078083A1/es unknown
- 2010-07-27 US US12/844,148 patent/US8193121B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US8193121B2 (en) | 2012-06-05 |
| US20110053779A1 (en) | 2011-03-03 |
| IN2012DN00773A (enExample) | 2015-06-26 |
| EA201270089A1 (ru) | 2012-09-28 |
| KR20120038542A (ko) | 2012-04-23 |
| JP2013500285A (ja) | 2013-01-07 |
| AU2010278335A1 (en) | 2012-02-16 |
| DK2459528T3 (da) | 2013-07-08 |
| CN102548960A (zh) | 2012-07-04 |
| BR112012001940B1 (pt) | 2018-06-19 |
| WO2011012247A1 (de) | 2011-02-03 |
| MX2012001155A (es) | 2012-02-13 |
| EP2459528B1 (de) | 2013-05-15 |
| KR101767519B1 (ko) | 2017-08-11 |
| WO2011012247A8 (de) | 2011-12-29 |
| BR112012001940A2 (pt) | 2016-03-15 |
| EP2459528A1 (de) | 2012-06-06 |
| AR078083A1 (es) | 2011-10-12 |
| JP5795315B2 (ja) | 2015-10-14 |
| CA2769451A1 (en) | 2011-02-03 |
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