WO2023030936A1 - Composés thioéthers contenant une fraction uracile destinés à être utilisés en tant qu'herbicides - Google Patents
Composés thioéthers contenant une fraction uracile destinés à être utilisés en tant qu'herbicides Download PDFInfo
- Publication number
- WO2023030936A1 WO2023030936A1 PCT/EP2022/073275 EP2022073275W WO2023030936A1 WO 2023030936 A1 WO2023030936 A1 WO 2023030936A1 EP 2022073275 W EP2022073275 W EP 2022073275W WO 2023030936 A1 WO2023030936 A1 WO 2023030936A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- alkyl
- thioethers
- methyl
- amino
- Prior art date
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- 150000003568 thioethers Chemical class 0.000 title claims abstract description 150
- 239000004009 herbicide Substances 0.000 title claims abstract description 31
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical group O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 97
- 238000000034 method Methods 0.000 claims abstract description 31
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 27
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims description 54
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 34
- 229910052731 fluorine Inorganic materials 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 229910052801 chlorine Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 18
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 239000004094 surface-active agent Substances 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229910052727 yttrium Inorganic materials 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- 150000007970 thio esters Chemical class 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 230000001276 controlling effect Effects 0.000 abstract 2
- -1 olamine salt Chemical class 0.000 description 378
- 241000196324 Embryophyta Species 0.000 description 59
- 238000009472 formulation Methods 0.000 description 54
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 44
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 44
- 238000006243 chemical reaction Methods 0.000 description 41
- 239000002904 solvent Substances 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 30
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 30
- 229910052783 alkali metal Inorganic materials 0.000 description 29
- 239000000460 chlorine Substances 0.000 description 29
- 150000001340 alkali metals Chemical class 0.000 description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000002585 base Substances 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 240000008042 Zea mays Species 0.000 description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 22
- 108090000623 proteins and genes Proteins 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000002253 acid Substances 0.000 description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000003960 organic solvent Substances 0.000 description 18
- 244000068988 Glycine max Species 0.000 description 16
- 235000010469 Glycine max Nutrition 0.000 description 16
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 16
- 235000014113 dietary fatty acids Nutrition 0.000 description 16
- 239000000194 fatty acid Substances 0.000 description 16
- 229930195729 fatty acid Natural products 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 14
- 108700019146 Transgenes Proteins 0.000 description 14
- 239000013543 active substance Substances 0.000 description 14
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 14
- 244000038559 crop plants Species 0.000 description 14
- 150000004820 halides Chemical class 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 13
- 238000011282 treatment Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 12
- 241000482268 Zea mays subsp. mays Species 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 235000005822 corn Nutrition 0.000 description 12
- 150000004665 fatty acids Chemical class 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 10
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 10
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 10
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 10
- 229940093499 ethyl acetate Drugs 0.000 description 10
- 235000019439 ethyl acetate Nutrition 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 10
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000010 aprotic solvent Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 238000006193 diazotization reaction Methods 0.000 description 9
- 239000012895 dilution Substances 0.000 description 9
- 238000010790 dilution Methods 0.000 description 9
- 239000000395 magnesium oxide Substances 0.000 description 9
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 9
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 150000002825 nitriles Chemical class 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 230000009261 transgenic effect Effects 0.000 description 9
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 235000013877 carbamide Nutrition 0.000 description 8
- 150000001879 copper Chemical class 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000002703 mutagenesis Methods 0.000 description 8
- 231100000350 mutagenesis Toxicity 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical class CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 7
- 235000006008 Brassica napus var napus Nutrition 0.000 description 7
- 240000000385 Brassica napus var. napus Species 0.000 description 7
- 229920000742 Cotton Polymers 0.000 description 7
- 241000219146 Gossypium Species 0.000 description 7
- 241000238631 Hexapoda Species 0.000 description 7
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- 150000002170 ethers Chemical class 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 7
- 150000003672 ureas Chemical class 0.000 description 7
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical class CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical class CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
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- 150000001342 alkaline earth metals Chemical class 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000003086 colorant Substances 0.000 description 6
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 6
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- 125000001153 fluoro group Chemical group F* 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
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- 150000002828 nitro derivatives Chemical class 0.000 description 6
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 241000894007 species Species 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 239000000080 wetting agent Substances 0.000 description 6
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- 244000020551 Helianthus annuus Species 0.000 description 5
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000002671 adjuvant Substances 0.000 description 5
- 229910000318 alkali metal phosphate Inorganic materials 0.000 description 5
- 229910000316 alkaline earth metal phosphate Inorganic materials 0.000 description 5
- 239000002168 alkylating agent Substances 0.000 description 5
- 229940100198 alkylating agent Drugs 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910000019 calcium carbonate Inorganic materials 0.000 description 5
- 239000001506 calcium phosphate Substances 0.000 description 5
- 229910000389 calcium phosphate Inorganic materials 0.000 description 5
- 235000011010 calcium phosphates Nutrition 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
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- 239000008187 granular material Substances 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 230000000749 insecticidal effect Effects 0.000 description 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 5
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- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 5
- 229910052808 lithium carbonate Inorganic materials 0.000 description 5
- 229910000103 lithium hydride Inorganic materials 0.000 description 5
- 229910000032 lithium hydrogen carbonate Inorganic materials 0.000 description 5
- HQRPHMAXFVUBJX-UHFFFAOYSA-M lithium;hydrogen carbonate Chemical compound [Li+].OC([O-])=O HQRPHMAXFVUBJX-UHFFFAOYSA-M 0.000 description 5
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 5
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- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 4
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- 240000005979 Hordeum vulgare Species 0.000 description 4
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
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- 230000000505 pernicious effect Effects 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000004477 pesticide formulation type Substances 0.000 description 1
- QIIPQYDSKRYMFG-UHFFFAOYSA-N phenyl hydrogen carbonate Chemical class OC(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
- 150000008048 phenylpyrazoles Chemical class 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical class NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical class NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 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 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 235000012015 potatoes Nutrition 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
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000000746 purification Methods 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
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 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
- 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
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 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
- 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
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000002708 random mutagenesis Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000013526 red clover Nutrition 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 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
- 238000000926 separation method Methods 0.000 description 1
- 238000004904 shortening Methods 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
- 239000002002 slurry Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 238000001694 spray drying 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
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 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
- 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
- 230000008685 targeting Effects 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 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
- 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
- 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
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 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
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229940047183 tribulus Drugs 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-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
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 244000052613 viral pathogen Species 0.000 description 1
- 244000000187 viroid pathogen Species 0.000 description 1
- 230000003612 virological effect Effects 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
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- 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
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P13/00—Herbicides; Algicides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Definitions
- the present invention relates to thioethers of formula (I) defined below and to their use as herbicides.
- WO 11/137088 describes structurally similar compounds for which herbicidal action is stated.
- thioethers of formula (I) having improved herbicidal action.
- thioethers of formula (I) which have high herbicidal activity, in particular even at low application rates, and which are sufficiently compatible with crop plants for commercial utilization.
- R 1 hydrogen, halogen Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy
- R 2 hydrogen, halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy
- R 3 hydrogen, halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy
- R 5 halogen, CN, NH 2 , NO 2 ;
- R 6 H halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy
- R 9 is hydrogen, Ci-Ce-alkyl, Cs-Ce-alkenyl, Cs-Ce-alkynyl, Ci-Ce-haloalkyl, C3-C6- haloalkenyl, Cs-Ce-haloalkynyl, Ci-Ce-cyanoalkyl, Ci-Ce-alkoxy-Ci-Ce-alkyl, C1- Ce-alkoxy-Ci-Ce-alkoxy-Ci-Ce-alkyl, di(Ci-C6-alkoxy)Ci-C6-alkyl, Ci-Ce-halo- alkoxy-Ci-Ce-alkyl, Cs-Ce-alkenyloxy-Ci-Ce-alkyl, Cs-Ce-haloalkenyloxy-Ci-Ce- alkyl, Cs-Ce-alkenyloxy-Ci-Ce-alkoxy-Ci-Ce-al
- -N CR 12 R 13 , wherein R 12 and R 13 independently of one another are H, C1-C4- alkyl or phenyl;
- the present invention provides thioethers of formula (I) wherein the substituents have the following meanings:
- R 9 is H, Ci-Ce-alkyl or Ci-Ce-alkoxy-Ci-Ce-alkyl; n 1;
- Z CH or N including their agriculturally acceptable salts, amides, esters or thioesters, provided the thioethers of formula (I) have a carboxyl group.
- the present invention also provides formulations comprising at least one thioether of formula (I) and auxiliaries customary for formulating crop protection agents.
- the present invention also provides the use of thioethers of formula (I) as herbicides, i.e. for controlling undesired vegetation.
- the present invention furthermore provides a method for controlling undesired vegetation where a herbicidal effective amount of at least one thioether of the formula (I) is allowed to act on plants, their seeds and/or their habitat.
- the invention relates to processes and intermediates for preparing thioethers of formula (I).
- thioethers of formula (I) as described herein are capable of forming geometrical isomers, for example E/Z isomers, it is possible to use both, the pure isomers and mixtures thereof, according to the invention.
- thioethers of formula (I) as described herein have one or more centres of chirality and, as a consequence, are present as enantiomers or diastereomers, it is possible to use both, the pure enantiomers and diastereomers and their mixtures, according to the invention.
- thioethers of formula (I) as described herein have ionizable functional groups, 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 hydrogen atoms are replaced by Ci-C4-alkyl, hydroxy-Ci-C4-alkyl, C1-C4- alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diethylammonium, diisopropylammonium, trimethylammonium, triethylammonium, tris(isopropyl)ammonium, heptylammonium, dodecylammonium, tetrade
- Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogensulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.
- Thioethers of formula (I) as described herein having a carboxyl group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agriculturally acceptable derivative, for example as amides, such as mono- and di- Ci-Ce-alkylamides or arylamides, as esters, for example as allyl esters, propargyl esters, C1-C10- alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2-yl)methyl) esters and also as thioesters, for example as Ci-Cw-alkylthio esters.
- amides such as mono- and di- Ci-Ce-alkylamides or arylamides
- esters for example as allyl esters, propargyl esters, C1-C10- alkyl esters, alkoxyalkyl esters, tefuryl ((te
- Preferred mono- and di-Ci-Ce-alkylamides are the methyl and the dimethylamides.
- Preferred arylamides are, for example, the anilides and the 2-chloroanilides.
- Preferred alkyl esters are, for example, 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, for example the 2-methoxyethyl, 2-ethoxyethyl, 2- butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropyl ester.
- An example of a straight-chain or branched Ci-Cw-alkylthio ester is the ethylthio ester.
- the organic moieties mentioned in the definition of the variables R 1 to R 14 are - like the term halogen - collective terms for individual enumerations of the individual group members.
- the term halogen denotes in each case fluorine, chlorine, bromine or iodine. All hydrocarbon 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.
- Ci-Cs-alkyl for example CH3, C2H5, n-propyl and CH(CH3)2;
- Ci-C4-alkyl and also the Ci-C4-alkyl moieties of phenyl-Ci-C4-alkyl for example CH3, C2H5, 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-C4-haloalkyl Ci-C4-alkyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 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, 2-fluoropropy
- Ci-Ce-haloalkyl Ci-C4-haloalkyl as mentioned above, and also, for example,
- C2-C4-alkenyl for example ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2- butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1 -propenyl, 1-methyl-2-propenyl, 2-methyl-2- propenyl,
- Cs-Ce-haloalkenyl and also the Cs-Ce-haloalkenyl moieties of Cs-Ce-haloalkenyloxy-Ci-Ce- alkyl a Cs-Ce-alkenyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example 2-chloroprop-2-en-1-yl, 3-chloroprop-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-tribrom
- C2-C4-alkynyl for example ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2-propynyl ;
- Cs-Ce-haloalkynyl a Cs-Ce-alkynyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example 1 ,1 -difl uoroprop-2-yn-1-yl,
- Ci-Cs-alkoxy for example methoxy, ethoxy, propoxy
- Ci-C4-alkoxy and also the Ci-C4-alkoxy moieties of Ci-C4-alkyoxycarbonyl for example methoxy, ethoxy, propoxy, 1 -methylethoxy butoxy, 1 -methylpropoxy, 2-methylpropoxy and 1 ,1- dimethylethoxy;
- 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., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2- fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2- trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,
- Ci-C4-alkylthio for example methylthio, ethylthio, propylthio, 1 -methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio and 1 , 1-dimethylethylthio;
- Ci-Ce-alkylsulfonyl (Ci-Ce-alkyl-S(O)2-) and also the Ci-Ce-alkylsulfonyl moieties of Ci-Ce- alkylsulfonyl-Ci-Ce-alkyl: for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1- methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methyl-propylsulfonyl, 1 ,1- dimethylethylsulfonyl, pentylsulfonyl, 1 -methylbutylsulfonyl, 2-methylbutylsulfonyl, 3- methylbutylsulfonyl, 1 ,1-dimethylpropylsulfonyl, 1 ,2-dimethylpropy
- (Ci-C4-alkyl)amino for example methylamino, ethylamino, propylamino, 1 -methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino or 1 ,1 -dimethylethylamino;
- Ca-Ce-heterocyclyl and also the heterocyclyl moieties of Cs-Ce-heterocyclyl-Ci-Ce-alkyl aliphatic heterocycle having 3 to 6 ring members which, in addition to carbon atoms, containsl to 4 nitrogen atoms, or 1 to 3 nitrogen atoms and an oxygen or sulphur atom, or an oxygen or a sulphur atom, for example three- or four-membered heterocycles like 2-oxetanyl, 3-oxetanyl, 2-thietanyl, 3-thietanyl, 1- azetidinyl, 2-azetidinyl, 1-azetinyl, 2-azetinyl; five-membered saturated heterocycles like 2- tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1 -pyrrolidinyl,2- pyrrol
- 5- or 6 membered heteroaryl aromatic heteroaryl having 5 or 6 ring members which, in addition to carbon atoms, contains 1 to 4 nitrogen atoms, or 1 to 3 nitrogen atoms and an oxygen or sulphur atom, or an oxygen or a sulphur atom, for example 5-membered aromatic rings like furyl (for example 2-furyl, 3-furyl), thienyl (for example 2-thienyl, 3-thienyl), pyrrolyl (for example pyrrol-2-yl, pyrrol-3-yl), pyrazolyl (for example pyrazol-3-yl, pyrazol-4-yl), isoxazolyl (for example isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl), isothiazolyl (for example isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl), imidazolyl (for example imidazo
- R 3 is H or halogen; preferably is H, F or Cl; more preferred is F or Cl; especially preferred is F.
- R 4 is H, F or Cl; particularly preferred is F or Cl; especially preferred is F.
- R 5 is halogen or CN; preferably F, Cl, Br or CN; particularly preferred is F, Cl or Br; especially preferred is Cl or Br; more preferred is Cl; also more preferred is Br.
- R 6 is H, F, Cl, Br, CH 3 or OCH 3 ; particularly preferred is H, CH 3 or OCH 3 ; especially preferred is H.
- R 7 is Ci-C 3 -alkoxy; particularly preferred is OCH 3 .
- R 8 is OR 9 , SR 9 or NR 9 S(O) 2 R 10 ; particularly preferred is OR 9 .
- R 9 is hydrogen, Ci-Ce-alkyl, C 3 -Ce-alkenyl, C 3 -Ce-alkynyl, Ci-Ce-haloalkyl, C 3 -Ce-haloalkenyl, C 3 -Ce-haloalkynyl, Ci-Ce-cyanoalkyl, Ci-Ce-alkoxy-Ci-Ce-alkyl, Ci-Ce-alkoxy-Ci-Ce- alkoxy-Ci-Ce-alkyl, Ci-Ce-alkylthio-Ci-Ce-alkyl, Ci-Ce-alkylsulfinyl-Ci-Ce-alkyl, Ci-Ce- alkylsulfonyl-Ci-Ce-alkyl, Ci-Ce-alkoxycarbonyl-Ci-Ce-alkyl, C 3 -C6-cycloalkyl, C 3 -Ce- cyclo
- R 10 is Ci-Ce-alkyl, Cs-Ce-alkenyl, Cs-Ce-alkynyl, Ci-Ce-haloalkyl, Cs-Ce-haloalkenyl, C3-C6- haloalkynyl, Ci-Ce-cyanoalkyl, Ci-Ce-alkoxy-Ci-Ce-alkyl, Ci-Ce-alkoxy-Ci-Ce-alkoxy- Ci-Ce-alkyl, Ci-Ce-alkylthio-Ci-Ce-alkyl, Ci-Ce-alkylsulfinyl-Ci-Ce-alkyl, Ci-Ce- alkylsulfonyl-Ci-Ce-alkyl, Ci-Ce-alkoxycarbonyl-Ci-Ce-alkyl, Cs-Ce-cycloalkyl, C3-C6- cycloalkyl-Ci-C
- R 11 is H, Ci-Ce-alkyl or Ci-Ce-alkoxycarbonyl-Ci-Ce-alkyl; particularly preferred is H or Ci-Ce-alkyl; more preferred is H; also more preferred is Ci-Ce-alkyl.
- R 12 is phenyl or Ci-C4-alkyl; particularly preferred is phenyl or CH3; also particularly preferred is phenyl; also particularly preferred is Ci-C4-alkyl.
- R 13 is phenyl or Ci-C4-alkyl; particularly preferred is phenyl or CH 3 ; also particularly preferred is phenyl; also particularly preferred is Ci-C4-alkyl.
- R 14 is halogen or Ci-Ce-alkyl; particularly preferred is F, Cl or CH3; also particularly preferred is halogen; especially preferred is F or Cl; also particularly preferred is Ci-Ce-alkyl; especially preferred is CH3.
- Q is O, also preferably is S.
- W is O, also preferably is S.
- Y 1 is O, also preferably is S.
- Y 2 is O, also preferably is S.
- Z is CH, also preferably is N.
- R° is CH 3 or NH 2 ;
- R 1 is halogen
- R 2 is halogen
- R 3 is hydrogen or halogen
- R 4 is H or halogen
- R 5 is halogen or CN
- R 6 is H, halogen, Ci-Cs-alkyl or Ci-Cs-alkoxy
- R 7 is Ci-Cs-alkoxy or Ci-Cs-alkylthio
- R 8 is OR 9 , SR 9 or NR 9 S(O) 2 R 10 , wherein
- R 9 is hydrogen, Ci-Ce-alkyl, Cs-Ce-alkenyl, Cs-Ce-alkynyl, Ci-Ce-haloalkyl, C3-C6- haloalkenyl, Cs-Ce-haloalkynyl, Ci-Ce-cyanoalkyl, Ci-Ce-alkoxy-Ci-Ce-alkyl, Ci-Ce- alkoxy-Ci-Ce-alkoxy-Ci-Ce-alkyl, Ci-Ce-alkylthio-Ci-Ce-alkyl, Ci-Ce-alkylsulfinyl-Ci- Ce-alkyl, Ci-Ce-alkylsulfonyl-Ci-Ce-alkyl, Ci-Ce-alkoxycarbonyl-Ci-Ce-alkyl, C3-C6- cycloalkyl, Cs-Ce-cycloalkyl-Ci
- R 10 is Ci-C 6 -alkyl; n is 1 ;
- Q is O or S
- W, Y 1 , Y 2 are O;
- Z is CH or N.
- R 1 is F
- R 2 is F
- R 3 is H, F or Cl
- R 4 is F or Cl
- R 5 is halogen or CN
- R 6 is H, F, Cl, Br, CH 3 or OCH 3 ;
- R 7 is Ci-C 3 -alkoxy
- R 8 is OR 9 , SR 9 or NR 9 S(O) 2 R 10 , wherein
- R 9 is hydrogen, Ci-Ce-alkyl, C 3 -Ce-alkenyl, C 3 -Ce-alkynyl, Ci-Ce-cyanoalkyl, Ci-Ce- alkoxy-Ci-Ce-alkyl, Ci-Ce-alkylthio-Ci-Ce-alkyl, Ci-Ce-alkoxycarbonyl-Ci-Ce-alkyl, C 3 - Ce-cycloalkyl, Cs-Ce-cycloalkyl-Ci-Ce-alkyl, C 3 -C6-heterocyclyl, C 3 -C6-heterocyclyl- Ci-Ce-alkyl, phenyl, phenyl-Ci-C4-alkyl;
- R 10 is Ci-C 6 -alkyl; n is 1 ;
- Q is O or S
- W, Y 1 , Y 2 are O;
- Z is CH or N.
- R° is CH 3 ;
- R 1 is F
- R 2 is F
- R 3 is F or Cl
- R 4 is F
- R 5 is F, Cl or Br
- R 6 is H
- R 7 is OCH 3 ;
- R 8 is OR 9 , wherein
- R 9 is hydrogen, Ci-Ce-alkyl, C 3 -Ce-alkenyl, C 3 -Ce-alkynyl, Ci-Ce-cyanoalkyl, Ci-Ce- alkoxy-Ci-Ce-alkyl, Ci-Ce-alkylthio-Ci-Ce-alkyl, Ci-Ce-alkoxycarbonyl-Ci-Ce-alkyl, C 3 - Ce-cycloalkyl, Cs-Ce-cycloalkyl-Ci-Ce-alkyl, C 3 -C6-heterocyclyl, C 3 -C6-heterocyclyl- Ci-Ce-alkyl, phenyl, phenyl-Ci-C4-alkyl; n is 1 ;
- Q is O or S
- W, Y 1 , Y 2 are O;
- Z is CH or N.
- R° is CH 3 ;
- R 1 is F
- R 2 is F
- R 3 is F or Cl
- R 4 is F
- R 5 is Cl or Br
- R 6 is H
- R 7 is OCH 3 ;
- R 8 is OR 9 , wherein
- R 9 is hydrogen, Ci-Ce-alkyl, Cs-Ce-alkenyl, Cs-Ce-alkynyl, Ci-Ce-alkoxy-Ci-Ce- alkyl; n is 1;
- Z is CH or N.
- R 2 is H or halogen
- R 5 is halogen or CN
- R 7 is Ci-Cs-alkoxy
- R 8 is OR 9 , wherein
- R 9 is H, Ci-C4-alkyl or Ci-C 6 -alkoxy-Ci-C 6 -alkyl;
- Z is CH or N.
- R 2 is H or F
- R 5 is F, Cl, BrorCN
- R 7 is OCH 3 ;
- R 8 is OR 9 , wherein
- R 9 is H, CH 3 , C2H5, CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 or CH 2 CH 2 OCH 3 ;
- thioethers of formula (l.a) corresponds to formula (I) wherein R° is CH3, R 1 is F, R 3 and R 4 are F, R 6 is H, n is 1, Q, W, Y 1 and Y 2 are O and Z is CH
- R 2 , R 5 , R 7 and R 8 have the meanings, in particular the preferred meanings, as defined above.
- thioethers of formula (l.b) particularly preferred the thioethers of formulae (l.b.1) to l.b.48, which differ from the corresponding thioethers of formulae (l.a.1) to (I. a.48) only in that Z is N:
- thioethers of formula (l.c) particularly preferred the thioethers of formulae (l.c.1) to (l.c.48), which differ from the corresponding thioethers of formulae (l.a.1) to (I. a.48) only in that Q is S:
- thioethers of formula (l.d) particularly preferred the thioethers of formulae (l.d.1) to (l.d.48), which differ from the corresponding thioethers of formulae (l.a.1) to (I. a.48) only in that Q is S and Z is N:
- the thioethers of formula (I) according to the invention can be prepared by standard processes of organic chemistry, for example by the following processes:
- the thioethers of formula (I) are obtained from the acid halides of formula (II) by reaction with compounds of formula (III) in the presence of a base:
- L 1 is halogen; preferably is F, Cl or Br; especially preferred is F or Cl, more preferred is Cl.
- acid halides of formula (II) instead of the acid halides of formula (II), also the corresponding acid (e.g. acid halide of formula (II), wherein L 1 is OH) in combination with an activating reagent, like carbonyldiimidazole, N,N'-dicyclohexylcarbodiimide (DCC), 1-ethyl-3-(3- dimethylaminopropyl)- , carbodiimide (EDC) or N-methyl-2-chloropyridinium chloride can be used.
- an activating reagent like carbonyldiimidazole, N,N'-dicyclohexylcarbodiimide (DCC), 1-ethyl-3-(3- dimethylaminopropyl)- , carbodiimide (EDC) or N-methyl-2-chloropyridinium chloride.
- an activating reagent like carbonyldiimidazole, N,N'-
- the compounds (III) can also be employed in the form of their salts, in particular the sodium and potassium salts, in which case the presence of a base is not necessary.
- the reaction of acid halides (II) with compounds (III) is usually carried out from 0 °C to the boiling point of the reaction mixture, preferably at from 0 °C to 100 °C, particularly preferably at from 0 °C to 40 °C, in an inert organic solvent in the presence of a base.
- the reaction may in principle be carried out in substance. However, preference is given to reacting the acid halides (II) with the compounds (III) in an organic solvent. Suitable in principle are all solvents, which are capable of dissolving the acid halides (II) and the compounds (III) at least partly, and preferably fully under reaction conditions.
- Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, nitromethane and mixtures of C5-C8-alkanes; aromatic hydrocarbons such as benzene, chlorobenzene, tolene, cresols, o-, m- and p-xylene; halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride and chlorobenzene; ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether (TBME), dioxane, anisole and tetra hydrofuran (THF); esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile; ketones such as acetone, methyl ethyl ketone, diethyl
- Preferred solvents are halogenated hydrocarbons, ethers and dipolar aprotic solvents as mentioned above.
- suitable bases include metal-containing bases and nitrogen-containing bases.
- suitable metal-containing bases are inorganic compounds such as alkali metal and alkaline earth metal oxide, and other metal oxides, such as lithium oxide, sodium oxide, potassium oxide, magnesium oxide, calcium oxide and magnesium oxide, iron oxide, silver oxide; alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride; alkali metal and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate, and calcium carbonate; alkali metal hydrogen carbonates (bicarbonates) such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; alkali metal and alkaline earth metal phosphates such as potassium phosphate, calcium phosphate; and furthermore organic bases, such as tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine, tributylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidinge, ter
- nitrogen-containing bases are C1-C6-alkylamines, preferably trialkylamines, for example triethylamine, trimethylamine, N-ethyhdiisopropyhamine; pyridine, lutidine, collidine, 4-(dimethylamino)pyridine (DMAP), imidazole, 1 ,8-diazabicyclo[5.4.0]undec-7- ene (DBU) or 1 ,5-diazabhcyclo- , [4.3.0]-'non-5-ene (DBN).
- C1-C6-alkylamines preferably trialkylamines, for example triethylamine, trimethylamine, N-ethyhdiisopropyhamine
- pyridine lutidine, collidine, 4-(dimethylamino)pyridine (DMAP), imidazole, 1 ,8-diazabicyclo[5.4.0]undec-7- ene (DBU) or
- Preferred bases are alkali metal and alkaline earth metal carbonates and nitrogen-containing bases as defined above; especially preferred triethylamine, pyridine or sodium carbonate.
- 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 generally used in excess, more preferably with from 1 to 3 equivalents based on the acid halides (II), and they may also be used as the solvent. However, they can also be employed in catalytic amounts.
- the acid halides (II), the compounds (III) and the base can be brought into contact in any way per se.
- reaction partners and the base may be introduced into the reaction vessel and reacted separately, simultaneously or successively.
- the reactants are generally employed in equimolar amounts. It might be advantageous using one of the reactants in excess, for example with a view to complete a reaction of the other reactant.
- the reaction can be carried out at atmospheric pressure, reduced pressure or under elevated pressure, if appropriate under an inert gas, continuously or batchwise.
- 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, for example 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 recrystallisation or digestion.
- the thioethers of formula (I) can also be prepared by reaction of compounds of formula (IV) with alkylating agents of formula (V) in the presence of a base in analogy to known processes (e.g.
- L 2 is a leaving group such halogen, Ci-Ce-alkyl- sulfonate or arylsulfonate; preferably Cl or Br.
- the reaction may in principle be carried out in substance. However, preference is given to reacting the compounds of formula (IV) with the alkylating agents of formula (V) in an organic solvent.
- Suitable in principle are all solvents which can dissolve the compounds of formula (IV) and the alkylating agents of formula (V) at least partly and preferably fully under reaction conditions.
- suitable solvents are ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether (TBME), dioxane, anisole and tetrahydrofuran (THF), esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, dimethylsulfoxide, N,N-dimethylformamide (DMF), N,N-dimethyl- acetamide (DMAC), 1 ,3-dimethyl-2-imidazolidinone (DMI), N,N'-dimethylpropylene urea (DMPLI), dimethyl sulfoxide (DMSO) and 1-methyl-2
- suitable metal-containing bases are inorganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminum hydroxide; alkali metal and alkaline earth metal oxide, and other metal oxides, such as lithium oxide, sodium oxide, potassium oxide, magnesium oxide, calcium oxide and magnesium oxide, iron oxide, silver oxide; alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate, cesium carbonate and calcium carbonate, as well as alkali metal hydrogen carbonates (bicarbonates) such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; alkali metal and alkaline earth metal phosphates such as lithium
- alkylating agents of formula (V) are commercially available or can be prepared by known methods (e.g. Lowell, Andrew N. et al, Tetrahedron, 6(30), 5573-5582, 2010; WO 11/137088).
- PG is a protecting group selected from the group consisting of Ci-Ce-alkyl, Ci-Ce--cyanoalkyl, Ci-Ce-haloalkyl, Ci-C6-alkylthio-C1-C4-alkyl, Ci-Ce- alkoxy- Ci-C4-alkyl, Ci-Ce-alkoxy- Ci-C4-alkoxy- Ci-C4-alkyl, (tri- Ci-Ce-alkyl)silyl- Ci-C4-alkyl, (tri- Ci-Ce-alkyl)silyl- Ci-C4-alkyoxy- Ci-C4-alkyl, C2-Ce-alkenyl, Cs-Ce-alkynyl, Cs-Ce-cycloalkyl, Cs-Ce-cylcloalkyl- Ci-C4-alkyl, Cs-Ce-cycloalkenyl, tetrahydr
- PG is Ci-Ce-alkyl, Ci-C6-alkoxy-Ci-C4-alkyl, (tri- Ci-Ce-alkyl)silyl-C1 -C4-alkyl, C2-C6- alkenyl, tetrahydropyranyl, (tri-Ci-C6-alkyl)silyl, [(diphenyl)(Ci-C4-alkyl)]silyl or phenyl-Ci-C4- alkyl.
- the compounds of formula (IV) can be prepared by treating the compounds of formula (VI), wherein “PG” is methyl, with boron tribromide in a solvent such as dichloromethane, acetonitrile or 1 ,4-dioxane, or without a solvent at temperatures ranging from 0 °C to 150 °C.
- a solvent such as dichloromethane, acetonitrile or 1 ,4-dioxane
- compounds of formula (IV) can be prepared by deprotecting compounds of formula (VI), wherein “PG” is a benzyl group, by catalytic hydrogenation in a hydrogen gas atmosphere at a pressure of 70 to 700 kPa, preferably 270 to 350 kPa, in the presence of a metal catalyst such as palladium supported on an inert carrier such as activated carbon, in a weight ratio of 5 to 20% of metal to carrier, suspended in a solvent such as ethanol at ambient temperature.
- PG is a benzyl group
- the Sandmeyer reaction is performed by diazotization with an alkyl nitrite (e.g. isoamyl nitrite, tert-Butyl nitrite or NaNO2) followed by treatment with a copper (I) and/or copper (II) halide (e.g. CuCI, CuCh, CuBr, CuBr2 or CuCN) in a solvent such as acetonitrile at a temperature ranging from 0 °C to the reflux temperature of the solvent to give the corresponding phenyluracils of formula (I), wherein R 5 is a Cl, Br or CN (e.g. WO 2011/137088, or L. Kurti, B. Czako Strategic Applications of Named Reactions in Organic Synthesis, Elsevier: San Diego, 2005, p. 394-395)
- an alkyl nitrite e.g. isoamyl nitrite, tert-Butyl nitrite or NaNO2
- reaction conditions can be used, adding instead of a copper salt an iodine salt such as potassium iodide after diazotization.
- tetrafluoroborate salts of the diazonium compound can be used. These are obtained by adding hydrogene tetrafluoroborate during the diazotization. Subsequent thermal or photolytical decomposition delivers the corresponding fluoro compounds (Langlois, B. In Introduction of Fluorine via Diazonium Compounds (Fluorodediazoniation); Baasner, B., Hagemann, H., Tatlow, J. C., Eds.; Houben- Weyl, Methods of Organic Chemistry; Thieme: Stuttgart, 1999; Vol. E10a, Organo-Fluorine Compounds, pp 686-740).
- the reaction of amino compounds of formula (VII) with a diazotization agent and optionally copper salts is usually carried out from 0°C to the boiling point of the reaction mixture, preferably from 0°C to 100°C, particularly preferably from 0°C to 40°C, in an inert solvent.
- the reaction may in principle be carried out in substance. However, preference is given to reacting the amino compounds of formula (VII) with the copper salts and the diazotization agent in an organic solvent.
- Suitable in principle are all solvents, which are capable of dissolving the amino compounds of formula (VII), the copper salts and the diazotization agent at least partly, and preferably fully under reaction conditions.
- Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, nitromethane and mixtures of C5-C8-alkanes; aromatic hydrocarbons such as benzene, chlorobenzene, tolene, cresols, o-, m- and p-xylene; halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride and chlorobenzene; ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether (TBME), dioxane, anisole and tetra hydrofuran (THF); esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile; ketones such as acetone, methyl ethyl ketone, diethyl
- Preferred solvents are nitriles or polar protic solvents as mentioned above. It is also possible to use mixtures of the solvents mentioned.
- the copper salts are generally used in excess, more preferably from 1 to 3 equivalents based on the amino compounds of formula (VII).
- the diazotization agent is generally used in excess, more preferably from 1 to 3 equivalents based on the amino compounds of formula (VII).
- the amino compounds of formula (VII), the copper salts and the diazotization agent can be brought into contact in any way per se.
- the reaction can be carried out at atmospheric pressure, reduced pressure or under elevated pressure, if appropriate under an inert gas, continuously or batchwise.
- the copper salts and the diazotization agents are commercially available.
- Amino compounds of formula (VII) can be prepared from nitro compounds of formula (VIII) using reduction conditions:
- the reduction of the nitro group on can be achieved by treatment with iron powder in acetic acid at a temperature ranging from 0 °C to 100 °C.
- the reduction can be carried out by catalytic hydrogenation in hydrogen gas at a pressure of 70 to 700 kPa, preferably 270 to 350 kPa, in the presence of a metal catalyst such as palladium supported on an inert carrier such as activated carbon, in a weight ratio of 5 to 20% of metal to carrier, suspended in a solvent such as ethanol at ambient temperature (see e.g. WO 2011/137088).
- the reaction of nitro compounds of formula (VIII) with the reducing agent is usually carried out from 0°C to the boiling point of the reaction mixture, preferably from 20°C to the boiling point of the reaction mixture, in an inert solvent.
- the reaction may in principle be carried out in substance.
- Suitable in principle are all solvents, which can dissolve the nitro compounds of formula (VIII), at least partly, and preferably fully under reaction conditions.
- Suitable solvents are alcohols such as ethanol.
- the reducing agents are generally used in excess, more preferably with from 1 to 6 equivalents based on the nitro compounds.
- the reaction can be carried out at atmospheric pressure, reduced pressure or under elevated pressure, if appropriate under an inert gas, continuously or batchwise.
- the reducing agents are commercially available.
- Nitro compounds of formula (VIII) can be prepared from compounds of formula (IX) in the presence of a base using compounds of formula (X):
- L 3 is a leaving group such halogen, Ci-Ce-alkylsulfonate or arylsulfonate; preferably F, Ci-Ce-alkylsulfonate or arylsulfonate; especially preferred F, mesylat or tosylat.
- reaction of the compounds of formula (IX) with compounds of formula (X) in presence of a base is usually carried out from 0°C to the boiling point of the reaction mixture, preferably from 20°C to 100°C.
- the reaction may in principle be carried out in substance. However, preference is given to reacting the compounds of formula (IX) with the compounds of formula (X) in an organic solvent. Suitable in principle are all solvents which can dissolve the compounds of formula (IX) and the compounds of formula (X) at least partly and preferably fully under reaction conditions.
- Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, nitromethane and mixtures of Cs-Cs-alkanes, aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1 ,2-dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether (TBME), dioxane, anisole and tetra hydrofuran (THF), esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfo
- Preferred solvents are ethers, nitriles and dipolar aprotic solvents as mentioned above.
- suitable metal-containing bases are inorganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminum hydroxide; alkali metal and alkaline earth metal oxide, and other metal oxides, such as lithium oxide, sodium oxide, potassium oxide, magnesium oxide, calcium oxide and magnesium oxide, iron oxide, silver oxide; alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate, cesium carbonate and calcium carbonate, as well as alkali metal hydrogen carbonates (bicarbonates) such as lithium hydrogen carbon
- L 4 is a leaving group such F, Ci-Ce-alkylsulfonate or arylsulfonate; preferably F, mesylat or tosylat;
- the reaction of the uracils of formula (XI) with compounds of formula (XII) in presence of a base is usually carried out from 0°C to the boiling point of the reaction mixture, preferably from 20°C to 100°C.
- the reaction may in principle be carried out in substance. However, preference is given to reacting the uracils of formula (XI) with the compounds of formula (XII) in an organic solvent.
- Suitable in principle are all solvents which can dissolve the uracils of formula (XI) and the compounds of formula (XII) at least partly and preferably fully under reaction conditions.
- suitable solvents are dipolar aprotic solvents such as sulfolane, dimethylsulfoxide, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1 ,3-dimethyl-2- imidazolidinone (DMI), N,N'-dimethylpropylene urea (DMPU), dimethyl sulfoxide (DMSO) and 1- methyl-2 pyrrolidinone (NMP).
- dipolar aprotic solvents such as sulfolane, dimethylsulfoxide, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1 ,3-dimethyl-2- imidazolidinone (DMI), N,N'-dimethylpropylene urea (DMPU
- suitable metal-containing bases are inorganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminum hydroxide; alkali metal and alkaline earth metal oxide, and other metal oxides, such as lithium oxide, sodium oxide, potassium oxide, magnesium oxide, calcium oxide and magnesium oxide, iron oxide, silver oxide; alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate, cesium carbonate and calcium carbonate, as well as alkali metal hydrogen carbonates (bicarbonates) such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; alkali metal and alkaline earth metal phosphates such as lithium
- reaction of the compounds of formula (XIII) in presence of an acid is usually carried out from 20°C to the boiling point of the reaction mixture, preferably from 50°C to 100°C.
- the reaction may in principle be carried out in substance. However, preference is given to reacting the compounds of formula (XIII) in an organic solvent.
- Suitable in principle are all solvents which can dissolve the compounds of formula (XIII) at least partly and preferably fully under reaction conditions.
- Suitable solvents are alcohols such as ethanol.
- Suitable acids are Bronsted acids, such as HCI or H2SO4.
- keto-esters of formula (XIV) with ureas of formula (XV) may in principle be carried out in substance. However, preference is given to reactions in an organic solvent. Suitable in principle are all solvents which can dissolve keto-esters of formula (XIV) and ureas of formula (XV) at least partly and preferably fully under reaction conditions.
- suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, dimethylsulfoxide, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1 ,3-dimethyl-2-imidazolidinone (DMI), N,N '-dimethylpropylene urea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2 pyrrolidinone (NMP).
- aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene
- nitriles such as acetonitrile and propionitrile
- keto-esters of formula (XIV) with ureas of formula (XV) is usually carried out from 20°C to the boiling point of the reaction mixture, preferably from 60°C to 140°C.
- Keto-esters of formula (XIV) can be prepared by reaction of esters of formula (XVI) with an acetic acid ester of formula (XVII) in the presence of a base:
- the reaction may be carried out in substance. However, it also possible reacting the esters of formula (XVI) with an acetic acid ester of formula (XVII) in an organic solvent.
- Suitable in principle are all solvents which can dissolve esters of formula (XVI) and an acetic acid ester of formula (XVII) at least partly and preferably fully under reaction conditions.
- Suitable solvents are ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether (TBME), dioxane, anisole and tetrahydrofuran (THF), esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, dimethylsulfoxide, N,N-dimethylformamide (DMF), N,N- dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N,N'-dimethylpropylene urea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2 pyrrolidinone (NMP).
- ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether (TBME), di
- suitable metal-containing bases are alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate, cesium carbonate and calcium carbonate, as well as alkali metal hydrogen carbonates (bicarbonates) such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; alkali metal and alkaline earth metal phosphates such as potassium phosphate, calcium phosphate; metal organic compounds, preferably alkali metal alkyls such as methyl lithium, butyl lithium and phenyl lithium, alkyl magnesium halides such as methyl magnesium chloride as well as alkali metal and alkaline earth metal alkoxides such as potassium tert-butoxide.
- alkali metal and alkaline earth metal hydrides such as lithium hydr
- Esters of formula (XVI) and acetic acid ester of formula (XVII) are known from literature and/or commercially available.
- the thioethers of formula (I) may be mixed with many representatives of other herbicidal or growth-regulating active ingredient groups and then applied concomitantly.
- Suitable components for combinations are, for example, herbicides from the classes of the acetamides, amides, aryloxyphenoxypropionates, benzamides, benzofuran, benzoic acids, benzothiadiazinones, bipyridylium, carbamates, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenol, diphenyl ether, glycines, imidazolinones, isoxazoles, isoxazolidinones, nitriles, N-phenylphthalimides, oxadiazoles, oxazolidinediones, oxyacetamides, phenoxycarboxylic acids, phenyl
- thioethers of formula (I) alone or in combination with other herbicides, or else in the form of a mixture with other crop protection agents, for example 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.
- the invention also relates to formulations comprising at least an auxiliary and at least one thioethers of formula (I) according to the invention.
- a formulation comprises a pesticidally effective amount of a thioether of formula (I).
- effective amount denotes an amount of the combination or of the thioethers of formula (I), which is sufficient for controlling undesired vegetation, especially for controlling undesired vegetation in crops (i.e. cultivated plants) and which does not result in a substantial damage to the treated crop plants.
- Such an amount can vary in a broad range and is dependent on various factors, such as the undesired vegetation to be controlled, the treated crop plants or material, the climatic conditions and the specific thioether of formula (I) used.
- the thioethers of formula (I), their N-oxides, salts amides, esters or thioesters can be converted into customary types of formulations, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
- formulation types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g.
- WP WP
- SP WS
- DP DS
- pressings e.g. BR, TB, DT
- granules e.g. WG, SG, GR, FG, GG, MG
- insecticidal articles e.g. LN
- gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF).
- the formulations are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
- Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
- Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g.
- toluene paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
- alcohols e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol
- glycols DMSO
- ketones e.g. cyclohexanone
- esters e.g. lactates, carbonates, fatty acid esters,
- Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
- mineral earths e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
- polysaccharides e.g. cellulose, starch
- fertilizers
- Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon’s, Vol.1: Emulsifiers & Detergents, McCutcheon’s Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
- Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof.
- sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates.
- Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
- Examples of phosphates are phosphate esters.
- Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
- Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
- alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
- Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
- N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
- esters are fatty acid esters, glycerol esters or monoglycerides.
- sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
- polymeric surfactants are home- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.
- Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
- Suitable amphoteric surfactants are alkylbetains and imidazolines.
- Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
- Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.
- Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the thioethers of formula (I) on the target.
- examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
- Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
- Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.
- Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
- Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
- Suitable colorants are pigments of low water solubility and water- soluble dyes.
- examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
- Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
- a thioether of formula (I) according to the invention 5-25 wt% of a thioether of formula (I) according to the invention and 1-10 wt% dispersant (e. g. polyvinylpyrrolidone) are dissolved in organic solvent (e.g. cyclohexanone) ad 100 wt%. Dilution with water gives a dispersion.
- dispersant e. g. polyvinylpyrrolidone
- organic solvent e.g. cyclohexanone
- a thioether of formula (I) 5-40 wt% of a thioether of formula (I) according to the invention and 1-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% waterinsoluble organic solvent (e.g. aromatic hydrocarbon).
- emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
- waterinsoluble organic solvent e.g. aromatic hydrocarbon
- a thioether of formula (I) In an agitated ball mill, 20-60 wt% of a thioether of formula (I) according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1-2 wt% thickener (e.g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type formulation up to 40 wt% binder (e.g. polyvinylalcohol) is added.
- WG, SG Water-dispersible granules and water-soluble granules
- thioether of formula (I) 50-80 wt% of a thioether of formula (I) according to the invention are ground finely with addition of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
- dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
- a thioether of formula (I) 50-80 wt% of a thioether of formula (I) according to the invention are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (e.g. sodium lignosulfonate), 1-3 wt% wetting agents (e.g. alcohol ethoxylate) and solid carrier (e.g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance.
- dispersants e.g. sodium lignosulfonate
- wetting agents e.g. alcohol ethoxylate
- solid carrier e.g. silica gel
- a thioether of formula (I) In an agitated ball mill, 5-25 wt% of a thioether of formula (I) according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1-5 wt% thickener (e.g. carboxymethylcellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
- dispersants e.g. sodium lignosulfonate
- 1-5 wt% thickener e.g. carboxymethylcellulose
- a thioether of formula (I) 5-20 wt% are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
- organic solvent blend e.g. fatty acid dimethylamide and cyclohexanone
- surfactant blend e.g. alcohol ethoxylate and arylphenol ethoxylate
- An oil phase comprising 5-50 wt% of a thioether of formula (I) according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules.
- an oil phase comprising 5-50 wt% of a thioether of formula (I) according to the invention, 0-40 wt% water insoluble organic solvent (e.g.
- a thioether of formula (I) according to the invention are ground finely and mixed intimately with solid carrier (e.g. finely divided kaolin) ad 100 wt%.
- solid carrier e.g. finely divided kaolin
- according to the invention is ground finely and associated with solid carrier (e.g. silicate) ad 100 wt%.
- solid carrier e.g. silicate
- Granulation is achieved by extrusion, spray-drying or the fluidized bed.
- a thioether of formula (I) 1-50 wt% of a thioether of formula (I) according to the invention are dissolved in organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%.
- organic solvent e.g. aromatic hydrocarbon
- the formulation types i) to xi) may optionally comprise further auxiliaries, such as 0,1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1-1 wt% anti-foaming agents, and 0,1-1 wt% colorants.
- the formulations generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of the thioether of formula (I).
- the thioethers of formula (I) are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
- Solutions for seed treatment (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds.
- the formulations in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations.
- Methods for applying thioethers of formula (I), formulations thereof, on to plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material.
- thioethers of formula (I), formulations thereof, respectively are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
- oils e.g. herbicides, insecticides, fungicides, growth regulators, safeners
- pesticides e.g. herbicides, insecticides, fungicides, growth regulators, safeners
- thioethers of formula (I) may be added to the thioethers of formula (I), the formulations comprising them as premix or, if appropriate not until immediately prior to use (tank mix).
- These agents can be admixed with the formulations according to the invention in a weight ratio of 1 :100 to 100:1, preferably 1 :10 to 10:1.
- the user applies the thioethers of formula (I) according to the invention, the formulations comprising them usually from a pre-dosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
- the formulation is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the formulation according to the invention is thus obtained.
- 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
- either individual components of the formulation according to the invention or partially premixed components e. g. components comprising thioethers of formula (I) may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
- individual components of the formulation according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
- either individual components of the formulation according to the invention or partially premixed components, e. g components comprising thioethers of formula (I) can be applied jointly (e.g. after tank mix) or consecutively.
- the thioethers of formula (I), are suitable as herbicides. They are suitable as such or as an appropriately formulation.
- the thioethers of formula (I), or the formulations comprising the thioethers of formula (I), control undesired vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and grass weeds in crops such as wheat, rice, maize, soya and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
- the thioethers of formula (I), or the formulations comprising the thioethers of formula (I) have an outstanding herbicidal activity against undesired vegetation, i.e. against a broad spectrum of economically important harmful monocotyledonous and dicotyledonous weeds.
- the thioethers of formula (I), or the formulations comprising the thioethers of formula (I) are used to control monocotyledonous weeds.
- Examples of monocotyledonous weeds on which the thioethers of formula (I), or the formulations comprising the thioethers of formula (I) act efficiently are selected from the genera Hordeum spp., Echinochloa spp., Poa spp., Bromus spp., Digitaria spp., Eriochloa spp., Setaria spp., Pennisetum spp., Eleusine spp., Eragrostis spp., Panicum spp., Lolium spp., Brachiaria spp., Leptochloa spp., Avena spp., Cyperus spp., Axonopris spp., Sorghum spp., and Melinus spp..
- Preferred examples of monocotyledonous weeds on which the thioethers of formula (I), or the formulations comprising the thioethers of formula (I) act efficiently are selected from the species Hordeum murinum, Echinochloa crus-galli, Poa annua, Bromus rubens L., Bromus rigidus, Bromus secalinus L., Digitaria sanguinalis, Digitaria insularis, Eriochloa gracilis, Setaria faberi, Setaria viridis, Pennisetum glaucum, Eleusine indica, Eragrostis pectinacea, Panicum miliaceum, Lolium multiflorum, Brachiaria platyphylla, Leptochloa fusca, Avena fatua, Cyperus compressus, Cyperus esculentes, Axonopris offinis, Sorghum halapense, and Melinus repens.
- Especially preferred examples of monocotyledonous weeds on which the thioethers of formula (I), or the formulations comprising the thioethers of formula (I) act efficiently are selected from the species Echinochloa spp., Digitaria spp., Setaria spp., Eleusine spp. and Brachiarium spp.
- the thioethers of formula (I), or the formulations comprising the thioethers of formula (I) are used to control dicotyledonous weeds.
- dicotyledonous weeds on which the thioethers of formula (I), or the formulations comprising the thioethers of formula (I) act efficiently are selected from the genera Amaranthus spp., Erigeron spp., Conyza spp., Polygonum spp., Medicago spp., Mollugo spp., Cyclospermum spp., Stellaria spp., Gnaphalium spp., Taraxacum spp., Oenothera spp., Amsinckia spp., Erodium spp., Erigeron spp., Senecio spp., Lamium spp., Kochia spp., Chenopodium spp., Lactuca spp
- Preferred examples of dicotyledonous weeds on which the thioethers of formula (I), or the formulations comprising the thioethers of formula (I) act efficiently are selected from the species Amaranthus spinosus, Polygonum convolvulus, Medicago polymorpha, Mollugo verticillata, Cyclospermum leptophyllum, Stellaria media, Gnaphalium purpureum, Taraxacum offi cinale, Oenothera laciniata, Amsinckia intermedia, Erodium cicutarium, Erodium moschatum, Erigeron bonariensis (Conyza bonariensis), Senecio vulgaris, Lamium amplexicaule, Erigeron canadensis, Polygonum aviculare, Kochia scoparia, Chenopodium album, Lactuca serriola, Malva parviflora, Malva neglecta, Ipomoea hederacea, Ipomoea
- dicotyledonous weeds on which the thioethers of formula (I), or the formulations comprising the thioethers of formula (I) act efficiently are selected from the species Amaranthus spp., Erigeron spp., Conyza spp., Kochia spp. and Abutilon spp.
- the thioethers of formula (I), or the formulations comprising them are applied to the plants mainly by spraying the leaves.
- the application can be carried out using, for example, water as carrier by customary spraying techniques using spray liquor amounts of from about 100 to 1000 l/ha (for example from 300 to 400 l/ha).
- the thioethers of formula (I), or the formulations comprising them may also be applied by the low-volume or the ultra-low-volume method, or in the form of microgranules.
- thioethers of formula (I), or the formulations comprising them can be done before, during and/or after, preferably during and/or after, the emergence of the undesired vegetation.
- thioethers of formula (I), or the formulations can be carried out before or during sowing.
- the thioethers of formula (I), or the formulations comprising them can be applied pre-, postemergence or pre-plant, or together with the seed of a crop plant. It is also possible to apply the thioethers of formula (I), or the formulations comprising them, by applying seed, pretreated with the thioethers of formula (I), or the formulations comprising them, of a crop plant.
- application techniques may be used in which the combinations are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active ingredients reach the leaves of undesired vegetation growing underneath, or the bare soil surface (post-directed, lay-by).
- the thioethers of formula (I), or the formulations comprising them can be applied by treating seed.
- the treatment of seeds comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting) based on the thioethers of formula (I), or the formulations prepared therefrom.
- the combinations can be applied diluted or undiluted.
- seed comprises seed of all types, such as, for example, corns, seeds, fruits, tubers, seedlings and similar forms.
- seed describes corns and seeds.
- the seed used can be seed of the crop plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.
- the amounts of active substances applied i.e. the thioethers of formula (I) without formulation auxiliaries, are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.01 to 0.9 kg per ha and in particular from 0.02 to 0.5 kg per ha.
- the application rate of the thioethers of formula (I) is from 0.001 to 3 kg/ha, preferably from 0.005 to 2.5 kg/ha and in particular from 0.01 to 2 kg/ha of active substance (a.s.).
- the rates of application of the thioethers of formula (I) according to the present invention are from 0.1 g/ha to 3000 g/ha, preferably 10 g/ha to 1000 g/ha, depending on the control target, the season, the target plants and the growth stage.
- the application rates of the thioethers of formula (I) are in the range from 0.1 g/ha to 5000 g/ha and preferably in the range from 1 g/ha to 2500 g/ha or from 5 g/ha to 2000 g/ha.
- the application rate of the thioethers of formula (I) is 0.1 to 1000 g/ha, preferably 1 to 750 g/ha, more preferably 5 to 500 g/ha.
- amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.
- the amounts of active substances applied i.e. the thioethers of formula (I) are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.
- the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
- the thioethers of formula (I), or the formulations comprising them can additionally be employed in a further number of crop plants for eliminating undesired vegetation.
- all the crop plants (cultivated plants) mentioned herein are understood to comprise all species, subspecies, variants and/or hybrids which belong to the respective cultivated plants, including but not limited to winter and spring varieties, in particular in cereals such as wheat and barley, as well as oilseed rape, e.g. winter wheat, spring wheat, winter barley etc.
- corn is also known as Indian corn or maize (Zea mays) which comprises all kinds of corn such as field corn and sweet corn.
- all maize or corn subspecies and/or varieties are comprised, in particular flour corn (Zea mays var. amylacea), popcorn (Zea mays var. everta), dent corn (Zea mays var. indentata), flint corn (Zea mays var. indurata), sweet corn (Zea mays var. saccharata and var. rugosa), waxy corn (Zea mays var. ceratina), amylomaize (high amylose Zea mays varieties), pod corn or wild maize (Zea mays var. tunicata) and striped maize (Zea mays var. japonica).
- soybean cultivars are classifiable into indeterminate and determinate growth habit, whereas Glycine soja, the wild progenitor of soybean, is indeterminate (PNAS 2010, 107 (19) 8563-856).
- the indeterminate growth habit (Maturity Group, MG 00 to MG 4.9) is characterized by a continuation of vegetative growth after flowering begins whereas determinate soybean varieties (Maturity Group, (MG) 5 to MG 8) characteristically have finished most of their vegetative growth when flowering begins.
- all soybean cultivars or varieties are comprised, in particular indeterminate and determinate cultivars or varieties.
- Preferred crops are Arachis hypogaea, Beta vulgaris spec, altissima, Brassica napus var. napus, Brassica oleracea, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cynodon dactylon, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hordeum vulgare, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Medicago sativa, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa , Phaseolus lunatus, Phaseolus vulgaris, Pistacia vera, Pisum s
- Especially preferred crops are crops of cereals, corn, soybeans, rice, oilseed rape, cotton, peas, lentils, peanuts or permanent crops.
- thioethers of formula (I) according to the invention can also be used in crops which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.
- crops as used herein includes also (crop) plants which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.
- Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, but also techniques of targeted mutagenesis, in order to create mutations at a specific locus of a plant genome.
- Targeted mutagenesis techniques frequently use oligonucleotides or proteins like CRISPR/Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the targeting effect.
- Genetic engineering usually uses recombinant DNA techniques to create modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination.
- one or more genes are integrated into the genome of a plant in order to add a trait or improve a trait. These integrated genes are also referred to as transgenes in the art, while plant comprising such transgenes are referred to as transgenic plants.
- the process of plant transformation usually produces several transformation events, which differ in the genomic locus in which a transgene has been integrated. Plants comprising a specific transgene on a specific genomic locus are usually described as comprising a specific “event”, which is referred to by a specific event name. Traits which have been introduced in plants or have been modified include in particular herbicide tolerance, insect resistance, increased yield and tolerance to abiotic conditions, like drought.
- Herbicide tolerance has been created by using mutagenesis as well as using genetic engineering. Plants which have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbicides by conventional methods of mutagenesis and breeding comprise plant varieties commercially available under the name Clearfield®. However, most of the herbicide tolerance traits have been created via the use of transgenes.
- ALS acetolactate synthase
- Herbicide tolerance has been created to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides and 4- hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, like isoxaflutole and mesotrione.
- HPPD 4- hydroxyphenylpyruvate dioxygenase
- Transgenes which have been used to provide herbicide tolerance traits comprise: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621 and goxv247, for tolerance to glufosinate: pat and bar, for tolerance to 2,4-D: aad-1 and aad-12, for tolerance to dicamba: dmo, for tolerance to oxynil herbicies: bxn, for tolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA, for tolerance to ALS inhibitor herbicides: csr1-2, for tolerance to HPPD inhibitor herbicides: hppdPF, W336 and avhppd-03.
- Transgenic corn events comprising herbicide tolerance genes are for example, but not excluding others, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHG0JG, HCEM485, VCO- 01981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275.
- Transgenic soybean events comprising herbicide tolerance genes are for example, but not excluding others, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS- 81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127.
- Transgenic cotton events comprising herbicide tolerance genes are for example, but not excluding others, 19-51 a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701 , MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40.
- Transgenic canola events comprising herbicide tolerance genes are for example, but not excluding others, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1 , MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2 and RF3.
- Insect resistance has mainly been created by transferring bacterial genes for insecticidal proteins to plants.
- Transgenes which have most frequently been used are toxin genes of Bacillus spec, and synthetic variants thereof, like cry1A, crylAb, cry1Ab-Ac, crylAc, cry1A.1O5, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1 , cry34Ab1 , cry35Ab1 , cry9C, vip3A(a), vip3Aa20.
- genes of plant origin have been transferred to other plants.
- genes coding for protease inhibitors like CpTI and pinll.
- a further approach uses transgenes in order to produce double stranded RNA in plants to target and downregulate insect genes.
- An example for such a transgene is dvsnf7.
- Transgenic corn events comprising genes for insecticidal proteins or double stranded RNA are for example, but not excluding others, Bt10, Bt11 , Bt176, MON801 , MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418 and MZIR098.
- Transgenic soybean events comprising genes for insecticidal proteins are for example, but not excluding others, MON87701 , MON87751 and DAS-81419.
- Transgenic cotton events comprising genes for insecticidal proteins are for example, but not excluding others, SGK321 , MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601 , Eventl , COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119 and SGK321.
- Increased yield has been created by increasing ear biomass using the transgene athb17, being present in corn event MON87403, or by enhancing photosynthesis using the transgene bbx32, being present in the soybean event MON87712.
- Crops comprising a modified oil content have been created by using the transgenes: gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A and fatb1-A. Soybean events comprising at least one of these genes are: 260-05, MON87705 and MON87769.
- Tolerance to abiotic conditions, in particular to tolerance to drought, has been created by using the transgene cspB, comprised by the corn event MON87460 and by using the transgene Hahb- 4, comprised by soybean event IND-00410-5.
- Traits are frequently combined by combining genes in a transformation event or by combining different events during the breeding process.
- Preferred combination of traits are herbicide tolerance to different groups of herbicides, insect tolerance to different kind of insects, in particular tolerance to lepidopteran and coleopteran insects, herbicide tolerance with one or several types of insect resistance, herbicide tolerance with increased yield as well as a combination of herbicide tolerance and tolerance to abiotic conditions.
- Plants comprising singular or stacked traits as well as the genes and events providing these traits are well known in the art.
- detailed information as to the mutagenized or integrated genes and the respective events are available from websites of the organizations “International Service for the Acquisition of Agri-biotech Applications (ISAAA)” (http://www.isaaa.org/gmapprovaldatabase) and the “Center for Environmental Risk Assessment (CERA)” (http://cera-qmc.org/GMCropDatabase), as well as in patent applications, like EP3028573 and W02017/011288.
- ISAAA International Service for the Acquisition of Agri-biotech Applications
- CERA Center for Environmental Risk Assessment
- effects which are specific to a crop comprising a certain gene or event may result in effects which are specific to a crop comprising a certain gene or event. These effects might involve changes in growth behavior or changed resistance to biotic or abiotic stress factors. Such effects may in particular comprise enhanced yield, enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigour, early or delayed ripening, cold or heat tolerance as well as changed amino acid or fatty acid spectrum or content.
- plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve raw material production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).
- a modified amount of ingredients or new ingredients specifically to improve raw material production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).
- the thioethers of formula (I) according to the invention are also suitable for the defoliation and/or desiccation of plant parts of crops such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton.
- crops such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton.
- formulations for the desiccation and/or defoliation of crops processes for preparing these formulations and methods for desiccating and/or defoliating plants using the thioethers of formula (I) have been found.
- the thioethers of formula (I) are particularly suitable for desiccating the aboveground parts of crop plants such as potato, oilseed rape, sunflower and soybean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants. Also of economic interest is to facilitate harvesting, which is made possible by concentrating within a certain period of time the dehiscence, or reduction of adhesion to the tree, in citrus fruit, olives and other species and varieties of pernicious fruit, stone fruit and nuts. The same mechanism, i.e. the promotion of the development of abscission tissue between fruit part or leaf part and shoot part of the plants is also essential for the controlled defoliation of useful plants, in particular cotton.
- Example 1 - step 1 6-hydroxy-1-methyl-6-(trifluoromethyl)hexahydropyrimidine-2, 4-dione
- Example 1 - step 8 methyl 2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl]sul- fanylphenoxy]-2-methoxy-acetate
- the culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate.
- the seeds of the test plants were sown separately for each species.
- the active ingredients which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles.
- the containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the test plants had rooted. This cover caused uniform germination of the test plants, unless this had been impaired by the active ingredients.
- the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.
- test plants were kept at 10 - 25°C or 20 - 35°C, respectively.
- the test period extended over 2 to 3weeks. During this time, the test plants were tended, and their response to the individual treatments was evaluated.
- Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the test plants, or complete destruction of at least the aerial moieties, and 0 means no damage, or normal course of growth. A good herbicidal activity is given at values of at least 70 and a very good herbicidal activity is given at values of at least 85.
- test plants used in the greenhouse experiments were of the following species:
- the thioether I. a.38 (example) 1 applied post-emergent showed very good herbicidal activity against AMARE, CHEAL, POLCO and SETVI.
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Abstract
La présente invention concerne des thioéthers de formule (I) (I), ou leurs sels ou dérivés acceptables en agriculture, les variables étant définies conformément à la description, des compositions les comprenant et leur utilisation en tant qu'herbicides, c'est-à-dire pour lutter contre des plantes nuisibles, ainsi qu'un procédé de lutte contre la végétation indésirable qui consiste à permettre à une quantité efficace herbicide d'au moins un thioéther de formule (I) d'agir sur les plantes, leurs graines et/ou leur habitat.
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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US20040198607A1 (en) * | 2001-09-28 | 2004-10-07 | Nobuaki Mito | Herbicide composition |
US20040204318A1 (en) * | 2001-09-28 | 2004-10-14 | Nobuaki Mito | Sumitomo chemical company limited |
WO2011137088A1 (fr) | 2010-04-27 | 2011-11-03 | E. I. Du Pont De Nemours And Company | Uraciles herbicides |
EP3028573A1 (fr) | 2014-12-05 | 2016-06-08 | Basf Se | Utilisation d'un triazole fongicide sur des plantes transgéniques |
WO2017011288A1 (fr) | 2015-07-13 | 2017-01-19 | E I Du Pont De Nemours And Company | Éthers d'aryloxypyrimidinyle employés comme herbicides |
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2022
- 2022-08-22 WO PCT/EP2022/073275 patent/WO2023030936A1/fr unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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US20040198607A1 (en) * | 2001-09-28 | 2004-10-07 | Nobuaki Mito | Herbicide composition |
US20040204318A1 (en) * | 2001-09-28 | 2004-10-14 | Nobuaki Mito | Sumitomo chemical company limited |
WO2011137088A1 (fr) | 2010-04-27 | 2011-11-03 | E. I. Du Pont De Nemours And Company | Uraciles herbicides |
EP3028573A1 (fr) | 2014-12-05 | 2016-06-08 | Basf Se | Utilisation d'un triazole fongicide sur des plantes transgéniques |
WO2017011288A1 (fr) | 2015-07-13 | 2017-01-19 | E I Du Pont De Nemours And Company | Éthers d'aryloxypyrimidinyle employés comme herbicides |
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CAS, no. 7217-59-6 |
GREENE, T. W.WUTS, P. G. M.: "Protective Groups in Organic Synthesis", 2007, WILEY |
L. KURTIB. CZAKO: "Strategic Applications of Named Reactions in Organic Synthesis", 2005, T&F INFORMA, article "New developments in crop protection product formulation", pages: 394 - 395 |
LANGLOIS, B.: "Houben-Weyl, Methods of Organic Chemistry", vol. E10a, 1999, THIEME, article "In Introduction of Fluorine via Diazonium Compounds (Fluorodediazoniation", pages: 686 - 740 |
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