MXPA00005040A - Herbicides 3-(benzazol-4-yl)pyrimidine-dione-derivatives - Google Patents
Herbicides 3-(benzazol-4-yl)pyrimidine-dione-derivativesInfo
- Publication number
- MXPA00005040A MXPA00005040A MXPA/A/2000/005040A MXPA00005040A MXPA00005040A MX PA00005040 A MXPA00005040 A MX PA00005040A MX PA00005040 A MXPA00005040 A MX PA00005040A MX PA00005040 A MXPA00005040 A MX PA00005040A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- halogen
- carbonyl
- ethyl
- butyl
- Prior art date
Links
- 230000002363 herbicidal Effects 0.000 title claims description 26
- 239000004009 herbicide Substances 0.000 title claims description 9
- -1 1,3-propylene- Chemical class 0.000 claims abstract description 801
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 45
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 39
- 150000002367 halogens Chemical class 0.000 claims abstract description 39
- 239000000126 substance Substances 0.000 claims abstract description 37
- 239000011780 sodium chloride Substances 0.000 claims abstract description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 11
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 63
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 42
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- BTRZCXUPKJCHIB-UHFFFAOYSA-N 3-(1H-indol-4-yl)-1H-pyrimidine-2,4-dione Chemical class O=C1C=CNC(=O)N1C1=CC=CC2=C1C=CN2 BTRZCXUPKJCHIB-UHFFFAOYSA-N 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 14
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 11
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 10
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Chemical group 0.000 claims description 9
- 230000012010 growth Effects 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 7
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-Aminophenol Natural products NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229910052801 chlorine Chemical group 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 239000011737 fluorine Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 3
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 abstract description 2
- 239000005977 Ethylene Substances 0.000 abstract description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 12
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 abstract 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 169
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
- 239000000203 mixture Substances 0.000 description 47
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 46
- 238000006243 chemical reaction Methods 0.000 description 45
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 40
- 239000000047 product Substances 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 32
- 230000000875 corresponding Effects 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 28
- BZKBCQXYZZXSCO-UHFFFAOYSA-N sodium hydride Chemical compound [H-].[Na+] BZKBCQXYZZXSCO-UHFFFAOYSA-N 0.000 description 27
- 239000002253 acid Substances 0.000 description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
- 235000002639 sodium chloride Nutrition 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 21
- 239000002585 base Substances 0.000 description 20
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 19
- 101700067048 CDC13 Proteins 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical class ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
- 241000196324 Embryophyta Species 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical class ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 14
- 125000001309 chloro group Chemical group Cl* 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 125000001153 fluoro group Chemical group F* 0.000 description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 12
- 125000001931 aliphatic group Chemical group 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000003085 diluting agent Substances 0.000 description 12
- 125000005499 phosphonyl group Chemical group 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- 229910052783 alkali metal Inorganic materials 0.000 description 11
- 125000001246 bromo group Chemical group Br* 0.000 description 11
- 150000004292 cyclic ethers Chemical class 0.000 description 11
- XTHFKEDIFFGKHM-UHFFFAOYSA-N dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 11
- 239000003480 eluent Substances 0.000 description 11
- 125000002346 iodo group Chemical group I* 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 10
- 238000007792 addition Methods 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 10
- 235000011152 sodium sulphate Nutrition 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
- 239000012043 crude product Substances 0.000 description 9
- 235000011167 hydrochloric acid Nutrition 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 8
- MVZVDAGWAAZJPE-UHFFFAOYSA-N 1,2-xylene;1,3-xylene;1,4-xylene Chemical group CC1=CC=C(C)C=C1.CC1=CC=CC(C)=C1.CC1=CC=CC=C1C MVZVDAGWAAZJPE-UHFFFAOYSA-N 0.000 description 8
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M Lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N P-Toluenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 150000001340 alkali metals Chemical class 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- FHYUCVWDMABHHH-UHFFFAOYSA-N toluene;1,2-xylene Chemical compound CC1=CC=CC=C1.CC1=CC=CC=C1C FHYUCVWDMABHHH-UHFFFAOYSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000002798 polar solvent Substances 0.000 description 7
- 239000001184 potassium carbonate Substances 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 238000001291 vacuum drying Methods 0.000 description 7
- BZLVMXJERCGZMT-UHFFFAOYSA-N MeOtBu Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 125000005466 alkylenyl group Chemical group 0.000 description 6
- 238000005576 amination reaction Methods 0.000 description 6
- 150000001448 anilines Chemical class 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000004359 castor oil Substances 0.000 description 6
- 235000019438 castor oil Nutrition 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 6
- 150000008282 halocarbons Chemical class 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- 150000007530 organic bases Chemical class 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 150000001342 alkaline earth metals Chemical class 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 125000005997 bromomethyl group Chemical group 0.000 description 5
- 235000013877 carbamide Nutrition 0.000 description 5
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 5
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- WLOOYFSUYWVINT-UHFFFAOYSA-N 3-(2-amino-4-chloro-6-fluoro-3-hydroxyphenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=C(N)C(O)=C(Cl)C=C1F WLOOYFSUYWVINT-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N Cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- AXZWODMDQAVCJE-UHFFFAOYSA-L Tin(II) chloride Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 4
- CSRZQMIRAZTJOY-UHFFFAOYSA-N Trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 239000000010 aprotic solvent Substances 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000006606 n-butoxy group Chemical group 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 150000008512 pyrimidinediones Chemical class 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 235000011150 stannous chloride Nutrition 0.000 description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
- 125000004710 2-methylpropylthio group Chemical group CC(CS*)C 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- HCUYBXPSSCRKRF-UHFFFAOYSA-N Diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 3
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N O-Phenylenediamine Chemical class NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 229960003975 Potassium Drugs 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N Sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- NVIFVTYDZMXWGX-UHFFFAOYSA-N Sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 description 3
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 3
- 150000008046 alkali metal hydrides Chemical class 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 3
- 244000038559 crop plants Species 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000005712 crystallization Effects 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 125000004859 cyclopropyloxymethyl group Chemical group C1(CC1)OC* 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- NXVKRKUGIINGHD-ARJAWSKDSA-N ethyl (Z)-3-amino-4,4,4-trifluorobut-2-enoate Chemical compound CCOC(=O)\C=C(/N)C(F)(F)F NXVKRKUGIINGHD-ARJAWSKDSA-N 0.000 description 3
- 230000035784 germination Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000003701 inert diluent Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 229910052987 metal hydride Inorganic materials 0.000 description 3
- 150000004681 metal hydrides Chemical class 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N n-methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 230000000802 nitrating Effects 0.000 description 3
- RGVZMPONLYFINH-UHFFFAOYSA-N nitronium;tetrafluoroborate Chemical compound O=[N+]=O.F[B-](F)(F)F RGVZMPONLYFINH-UHFFFAOYSA-N 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- OCFVSFVLVRNXFJ-UHFFFAOYSA-N potassium hydride Inorganic materials [H-].[K+] OCFVSFVLVRNXFJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- 239000001187 sodium carbonate Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 229940001593 sodium carbonate Drugs 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000005987 sulfurization reaction Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical class OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- LEEAJXCPRNVDJR-UHFFFAOYSA-N 3,3-difluorobutylidyneoxidanium Chemical group [CH2-]C(F)(F)CC#[O+] LEEAJXCPRNVDJR-UHFFFAOYSA-N 0.000 description 2
- OQGKHTHNZRZBNW-UHFFFAOYSA-N 3-(4-chloro-6-fluoro-3-methoxy-2-nitrophenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound COC1=C(Cl)C=C(F)C(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1[N+]([O-])=O OQGKHTHNZRZBNW-UHFFFAOYSA-N 0.000 description 2
- 125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 description 2
- AEYUMNIQWATJPL-UHFFFAOYSA-N 5-fluoropentan-1-one Chemical group FCCCC[C]=O AEYUMNIQWATJPL-UHFFFAOYSA-N 0.000 description 2
- LYAHRTSQLUJLMX-UHFFFAOYSA-N 7-chloro-5-fluoro-1-methyl-2-(trifluoromethyl)benzimidazole Chemical compound FC1=CC(Cl)=C2N(C)C(C(F)(F)F)=NC2=C1 LYAHRTSQLUJLMX-UHFFFAOYSA-N 0.000 description 2
- HVDYICGGRPSJNB-UHFFFAOYSA-N 7-chloro-5-fluoro-4-isocyanato-1-methyl-2-(trifluoromethyl)benzimidazole Chemical compound FC1=CC(Cl)=C2N(C)C(C(F)(F)F)=NC2=C1N=C=O HVDYICGGRPSJNB-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- PZZYQPZGQPZBDN-UHFFFAOYSA-N Aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 241000335053 Beta vulgaris Species 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N Boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 229920001429 Chelating resin Polymers 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 240000007842 Glycine max Species 0.000 description 2
- 240000006962 Gossypium hirsutum Species 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N Hexamethylphosphoramide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N Isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- SRTHRWZAMDZJOS-UHFFFAOYSA-N Lithium hydride Chemical compound [H-].[Li+] SRTHRWZAMDZJOS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 240000006394 Sorghum bicolor Species 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- 240000007313 Tilia cordata Species 0.000 description 2
- 235000015450 Tilia cordata Nutrition 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N Trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- 240000008529 Triticum aestivum Species 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N [N-]=C=O Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 230000001464 adherent Effects 0.000 description 2
- 239000002156 adsorbate Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- DQPBABKTKYNPMH-UHFFFAOYSA-N amino hydrogen sulfate Chemical compound NOS(O)(=O)=O DQPBABKTKYNPMH-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Inorganic materials [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 125000004432 carbon atoms Chemical group C* 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 229910052570 clay Inorganic materials 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- RYPWQHONZWFXBN-UHFFFAOYSA-N dichloromethyl(methylidene)-$l^{3}-chlorane Chemical compound ClC(Cl)Cl=C RYPWQHONZWFXBN-UHFFFAOYSA-N 0.000 description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000005842 heteroatoms Chemical group 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 150000002905 orthoesters Chemical group 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
- 125000000177 propargylthio group Chemical group [H]C#CC([H])([H])S* 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 239000003638 reducing agent Substances 0.000 description 2
- 230000001105 regulatory Effects 0.000 description 2
- POECFFCNUXZPJT-UHFFFAOYSA-M sodium;carbonic acid;hydrogen carbonate Chemical compound [Na+].OC(O)=O.OC([O-])=O POECFFCNUXZPJT-UHFFFAOYSA-M 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- XTQHKBHJIVJGKJ-UHFFFAOYSA-O sulfanylideneoxidanium Chemical compound [SH+]=O XTQHKBHJIVJGKJ-UHFFFAOYSA-O 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2R,3R,4S,5R,6S)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2S,3R,4S,5R,6R)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2R,3R,4S,5R,6R)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 description 1
- SJSYJHLLBBSLIH-SDNWHVSQSA-N (E)-3-(2-methoxyphenyl)-2-phenylprop-2-enoic acid Chemical compound COC1=CC=CC=C1\C=C(\C(O)=O)C1=CC=CC=C1 SJSYJHLLBBSLIH-SDNWHVSQSA-N 0.000 description 1
- CRPTXKKKIGGDBX-UHFFFAOYSA-N (Z)-but-2-ene Chemical group [CH2]C=CC CRPTXKKKIGGDBX-UHFFFAOYSA-N 0.000 description 1
- GTIIVHODSNYECK-UHFFFAOYSA-N 1,1,1-trifluoropropane Chemical group [CH2]CC(F)(F)F GTIIVHODSNYECK-UHFFFAOYSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- 125000004711 1,1-dimethylethylthio group Chemical group CC(C)(S*)C 0.000 description 1
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 description 1
- 125000004515 1,2,4-thiadiazol-3-yl group Chemical group S1N=C(N=C1)* 0.000 description 1
- 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical class C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 1
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 description 1
- QLDQYRDCPNBPII-UHFFFAOYSA-N 1,2-benzoxazol-3-one Chemical class C1=CC=C2C(O)=NOC2=C1 QLDQYRDCPNBPII-UHFFFAOYSA-N 0.000 description 1
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 description 1
- 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 description 1
- MGNZXYYWBUKAII-UHFFFAOYSA-N 1,3-Cyclohexadiene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 1
- DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical compound C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 description 1
- WHUWQSQEVISUMC-UHFFFAOYSA-N 1,3-dimethyl-7-(2-methylpropyl)purine-2,6-dione Chemical group CN1C(=O)N(C)C(=O)C2=C1N=CN2CC(C)C WHUWQSQEVISUMC-UHFFFAOYSA-N 0.000 description 1
- XTKIUJCPLLOSMW-UHFFFAOYSA-N 1,4-Dioxyl radical Chemical group [CH]1COCCO1 XTKIUJCPLLOSMW-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 1,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 description 1
- WCIFVXNIHUSTHF-UHFFFAOYSA-N 1-bromopropane Chemical group [CH2]CCBr WCIFVXNIHUSTHF-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- BYLAWYTWAYOBDP-UHFFFAOYSA-N 1-chlorobutane Chemical group [CH2]CCCCl BYLAWYTWAYOBDP-UHFFFAOYSA-N 0.000 description 1
- YZNQITSGDRCUKE-UHFFFAOYSA-N 1-chloropropane Chemical group [CH2]CCCl YZNQITSGDRCUKE-UHFFFAOYSA-N 0.000 description 1
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- FNQIWGMVIKVMPH-UHFFFAOYSA-N 1-fluorobutane Chemical group [CH2]CCCF FNQIWGMVIKVMPH-UHFFFAOYSA-N 0.000 description 1
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- 125000006096 1-methylpropyl sulfinyl group Chemical group 0.000 description 1
- 125000004709 1-methylpropylthio group Chemical group CC(CC)S* 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000004781 2,2-dichloro-2-fluoroethyl group Chemical group [H]C([H])(*)C(F)(Cl)Cl 0.000 description 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 1
- MMUYPRGKZSIRKI-UHFFFAOYSA-N 2,2-difluoropropane-1-sulfinate Chemical group [CH2+]C(F)(F)CS([O-])=O MMUYPRGKZSIRKI-UHFFFAOYSA-N 0.000 description 1
- QZEDXQFZACVDJE-UHFFFAOYSA-N 2,3-dibutylnaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 QZEDXQFZACVDJE-UHFFFAOYSA-N 0.000 description 1
- CGNBQYFXGQHUQP-UHFFFAOYSA-N 2,3-dinitroaniline Chemical class NC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O CGNBQYFXGQHUQP-UHFFFAOYSA-N 0.000 description 1
- MHKBMNACOMRIAW-UHFFFAOYSA-N 2,3-dinitrophenol Chemical class OC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O MHKBMNACOMRIAW-UHFFFAOYSA-N 0.000 description 1
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminobenzenethiol Chemical class NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 1
- QTKHXEAIGWJFPO-UHFFFAOYSA-N 2-benzylbenzenethiol Chemical class SC1=CC=CC=C1CC1=CC=CC=C1 QTKHXEAIGWJFPO-UHFFFAOYSA-N 0.000 description 1
- CDMGNVWZXRKJNS-UHFFFAOYSA-N 2-benzylphenol Chemical class OC1=CC=CC=C1CC1=CC=CC=C1 CDMGNVWZXRKJNS-UHFFFAOYSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- 125000004780 2-chloro-2,2-difluoroethyl group Chemical group [H]C([H])(*)C(F)(F)Cl 0.000 description 1
- 125000004779 2-chloro-2-fluoroethyl group Chemical group [H]C([H])(*)C([H])(F)Cl 0.000 description 1
- XRAKCYJTJGTSMM-UHFFFAOYSA-N 2-chloro-4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1Cl XRAKCYJTJGTSMM-UHFFFAOYSA-N 0.000 description 1
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-N-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methylpent-1-ene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N 2-methylpropanenitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 125000006128 2-methylpropyl sulfonyl group Chemical group 0.000 description 1
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 1
- QBGQIMOGHUXVKB-UHFFFAOYSA-N 2-phenyl-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical class O=C1C(CCCC2)=C2C(=O)N1C1=CC=CC=C1 QBGQIMOGHUXVKB-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- REEXLQXWNOSJKO-UHFFFAOYSA-N 2H-1$l^{4},2,3-benzothiadiazine 1-oxide Chemical class C1=CC=C2S(=O)NN=CC2=C1 REEXLQXWNOSJKO-UHFFFAOYSA-N 0.000 description 1
- JSIAIROWMJGMQZ-UHFFFAOYSA-N 2H-triazol-4-amine Chemical class NC1=CNN=N1 JSIAIROWMJGMQZ-UHFFFAOYSA-N 0.000 description 1
- VZIHTQKMHLOIII-UHFFFAOYSA-N 3,5-dihydro-2H-furan Chemical group [CH]1CCOC1 VZIHTQKMHLOIII-UHFFFAOYSA-N 0.000 description 1
- BOHZXWVRUMXEED-UHFFFAOYSA-N 3-(4-chloro-2-fluoro-5-methoxyphenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound C1=C(Cl)C(OC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F BOHZXWVRUMXEED-UHFFFAOYSA-N 0.000 description 1
- NDDSFBUCSBTIAN-UHFFFAOYSA-N 3-(4-chloro-6-fluoro-3-hydroxy-2-nitrophenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=C(F)C=C(Cl)C(O)=C1[N+]([O-])=O NDDSFBUCSBTIAN-UHFFFAOYSA-N 0.000 description 1
- DRYHZNMEWLWQTR-UHFFFAOYSA-N 3-(7-chloro-5-fluoro-1-methylbenzotriazol-4-yl)-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione Chemical compound FC1=CC(Cl)=C2N(C)N=NC2=C1N1C(=O)C=C(C(F)(F)F)NC1=O DRYHZNMEWLWQTR-UHFFFAOYSA-N 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N 3-Pentanone Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- NFTWSUWBQWIBSH-UHFFFAOYSA-N 3-chloro-5-fluoro-2-N-methylbenzene-1,2-diamine Chemical compound CNC1=C(N)C=C(F)C=C1Cl NFTWSUWBQWIBSH-UHFFFAOYSA-N 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- KWXICGTUELOLSQ-UHFFFAOYSA-N 4-Dodecylbenzenesulfonic Acid Chemical compound CCCCCCCCCCCCC1=CC=C(S(O)(=O)=O)C=C1 KWXICGTUELOLSQ-UHFFFAOYSA-N 0.000 description 1
- FEPBITJSIHRMRT-UHFFFAOYSA-N 4-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1 FEPBITJSIHRMRT-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
- SPRIQTWHGNQKRN-UHFFFAOYSA-N 7-chloro-5-fluoro-1-methyl-4-nitro-2-(trifluoromethyl)benzimidazole Chemical compound FC1=CC(Cl)=C2N(C)C(C(F)(F)F)=NC2=C1[N+]([O-])=O SPRIQTWHGNQKRN-UHFFFAOYSA-N 0.000 description 1
- 235000005255 Allium cepa Nutrition 0.000 description 1
- 240000002840 Allium cepa Species 0.000 description 1
- DVARTQFDIMZBAA-UHFFFAOYSA-O Ammonium nitrate Chemical compound [NH4+].[O-][N+]([O-])=O DVARTQFDIMZBAA-UHFFFAOYSA-O 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N Ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 235000011446 Amygdalus persica Nutrition 0.000 description 1
- 240000002254 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 240000005781 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000005340 Asparagus officinalis Nutrition 0.000 description 1
- 240000001498 Asparagus officinalis Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N Benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 244000060924 Brassica campestris Species 0.000 description 1
- 235000005637 Brassica campestris Nutrition 0.000 description 1
- 244000178924 Brassica napobrassica Species 0.000 description 1
- 235000011297 Brassica napobrassica Nutrition 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 240000000385 Brassica napus var. napus Species 0.000 description 1
- HWKCSLSBMPIRJC-UHFFFAOYSA-N C(C)OC(=O)NC1=CC=CC=2NN=NC=21 Chemical compound C(C)OC(=O)NC1=CC=CC=2NN=NC=21 HWKCSLSBMPIRJC-UHFFFAOYSA-N 0.000 description 1
- 240000000239 Camellia sinensis Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N Carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 1
- 240000005801 Carthamus tinctorius Species 0.000 description 1
- 244000068645 Carya illinoensis Species 0.000 description 1
- 235000009025 Carya illinoensis Nutrition 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 240000002268 Citrus limon Species 0.000 description 1
- 240000002319 Citrus sinensis Species 0.000 description 1
- 235000005976 Citrus sinensis Nutrition 0.000 description 1
- 229940108066 Coal Tar Drugs 0.000 description 1
- 235000007460 Coffea arabica Nutrition 0.000 description 1
- 240000007154 Coffea arabica Species 0.000 description 1
- 241000228031 Coffea liberica Species 0.000 description 1
- 244000016593 Coffea robusta Species 0.000 description 1
- 235000002187 Coffea robusta Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N Cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- 240000008893 Cynodon dactylon Species 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- GUVUOGQBMYCBQP-UHFFFAOYSA-N DMPU Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 1
- NDUPDOJHUQKPAG-UHFFFAOYSA-N Dalapon Chemical compound CC(Cl)(Cl)C(O)=O NDUPDOJHUQKPAG-UHFFFAOYSA-N 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- 240000002860 Daucus carota Species 0.000 description 1
- PFBUKDPBVNJDEW-UHFFFAOYSA-N Dichlorocarbene Chemical group Cl[C]Cl PFBUKDPBVNJDEW-UHFFFAOYSA-N 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N Diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N Dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N Diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-N Disulfuric acid Chemical compound OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N Dodecanol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 235000001950 Elaeis guineensis Nutrition 0.000 description 1
- 240000003133 Elaeis guineensis Species 0.000 description 1
- 229940052303 Ethers for general anesthesia Drugs 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 240000001441 Fragaria vesca Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 235000014751 Gossypium arboreum Nutrition 0.000 description 1
- 240000001814 Gossypium arboreum Species 0.000 description 1
- 235000009429 Gossypium barbadense Nutrition 0.000 description 1
- 240000000047 Gossypium barbadense Species 0.000 description 1
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 1
- 240000002024 Gossypium herbaceum Species 0.000 description 1
- 235000009432 Gossypium hirsutum Nutrition 0.000 description 1
- 229940093912 Gynecological Sulfonamides Drugs 0.000 description 1
- 102100004109 HEY1 Human genes 0.000 description 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 240000006669 Helianthus annuus Species 0.000 description 1
- 240000008528 Hevea brasiliensis Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- 240000006600 Humulus lupulus Species 0.000 description 1
- 235000002678 Ipomoea batatas Nutrition 0.000 description 1
- 240000003613 Ipomoea batatas Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- CFHGBZLNZZVTAY-UHFFFAOYSA-N Lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
- 240000004322 Lens culinaris Species 0.000 description 1
- 235000010666 Lens esculenta Nutrition 0.000 description 1
- 229910010084 LiAlH4 Inorganic materials 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241000220225 Malus Species 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000004456 Manihot esculenta Nutrition 0.000 description 1
- 235000010624 Medicago sativa Nutrition 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 241000234295 Musa Species 0.000 description 1
- IQVDIWDSLGFLEL-UHFFFAOYSA-N N-(2-chloro-4-fluoro-6-nitrophenyl)-2,2,2-trifluoro-N-methylacetamide Chemical compound FC(F)(F)C(=O)N(C)C1=C(Cl)C=C(F)C=C1[N+]([O-])=O IQVDIWDSLGFLEL-UHFFFAOYSA-N 0.000 description 1
- BWRDLNUQULVMAA-UHFFFAOYSA-N N-(2-chloro-4-fluorophenyl)-2,2,2-trifluoroacetamide Chemical compound FC1=CC=C(NC(=O)C(F)(F)F)C(Cl)=C1 BWRDLNUQULVMAA-UHFFFAOYSA-N 0.000 description 1
- 241000208134 Nicotiana rustica Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 240000008962 Nicotiana tabacum Species 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N Nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N Nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- YLACRFYIUQZNIV-UHFFFAOYSA-N O-(2,4-dinitrophenyl)hydroxylamine Chemical compound NOC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O YLACRFYIUQZNIV-UHFFFAOYSA-N 0.000 description 1
- JZTPOMIFAFKKSK-UHFFFAOYSA-N O-phosphonohydroxylamine Chemical compound NOP(O)(O)=O JZTPOMIFAFKKSK-UHFFFAOYSA-N 0.000 description 1
- 235000002725 Olea europaea Nutrition 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000010617 Phaseolus lunatus Nutrition 0.000 description 1
- 240000002357 Phaseolus lunatus Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 240000005158 Phaseolus vulgaris Species 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N Phenylacetic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N Phenylpropanoic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- RWQFRHVDPXXRQN-UHFFFAOYSA-N Phosphorus sesquisulfide Chemical compound P12SP3SP1P2S3 RWQFRHVDPXXRQN-UHFFFAOYSA-N 0.000 description 1
- 244000193463 Picea excelsa Species 0.000 description 1
- 235000008124 Picea excelsa Nutrition 0.000 description 1
- 235000005205 Pinus Nutrition 0.000 description 1
- 241000218602 Pinus <genus> Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229920001451 Polypropylene glycol Polymers 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M Potassium bicarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N Potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 235000010401 Prunus avium Nutrition 0.000 description 1
- 240000002799 Prunus avium Species 0.000 description 1
- 240000005809 Prunus persica Species 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 240000001987 Pyrus communis Species 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 241001506137 Rapa Species 0.000 description 1
- 235000011483 Ribes Nutrition 0.000 description 1
- 241000220483 Ribes Species 0.000 description 1
- 210000000614 Ribs Anatomy 0.000 description 1
- 240000000528 Ricinus communis Species 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- 108060007468 SHOC2 Proteins 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N Sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 240000001016 Solanum tuberosum Species 0.000 description 1
- 235000007230 Sorghum bicolor Nutrition 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 229940090121 Sulfonylureas for blood glucose lowering Drugs 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N Tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 235000006468 Thea sinensis Nutrition 0.000 description 1
- 240000000280 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 235000004652 Tilia americana var heterophylla Nutrition 0.000 description 1
- 235000010840 Tilia tomentosa Nutrition 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N Trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 1
- 235000015724 Trifolium pratense Nutrition 0.000 description 1
- 240000002913 Trifolium pratense Species 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N Triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- 235000007264 Triticum durum Nutrition 0.000 description 1
- 241000209143 Triticum turgidum subsp. durum Species 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 235000007244 Zea mays Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- XIQPNCZCDTUCTM-UHFFFAOYSA-K [H+].[F-].[F-].[F-].[F-] Chemical compound [H+].[F-].[F-].[F-].[F-] XIQPNCZCDTUCTM-UHFFFAOYSA-K 0.000 description 1
- RLCUJBCFAPQEMA-UHFFFAOYSA-N [N+](=O)([O-])OC1=C(C=CC(=C1N)O[N+](=O)[O-])O Chemical compound [N+](=O)([O-])OC1=C(C=CC(=C1N)O[N+](=O)[O-])O RLCUJBCFAPQEMA-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K [O-]P([O-])([O-])=O Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000012445 acidic reagent Substances 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000005136 alkenylsulfinyl group Chemical group 0.000 description 1
- 125000005137 alkenylsulfonyl group Chemical group 0.000 description 1
- 125000005108 alkenylthio group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical group 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 230000002152 alkylating Effects 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000005133 alkynyloxy group Chemical group 0.000 description 1
- 125000005134 alkynylsulfinyl group Chemical group 0.000 description 1
- 125000005139 alkynylsulfonyl group Chemical group 0.000 description 1
- 125000005109 alkynylthio group Chemical group 0.000 description 1
- 230000000735 allogeneic Effects 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 125000004266 aziridin-1-yl group Chemical group [H]C1([H])N(*)C1([H])[H] 0.000 description 1
- 125000004267 aziridin-2-yl group Chemical group [H]N1C([H])([H])C1([H])* 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium(0) Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional Effects 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- HXCOCQWMKNUQSA-UHFFFAOYSA-N caesium hydride Inorganic materials [H-].[Cs+] HXCOCQWMKNUQSA-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 230000003197 catalytic Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 239000007931 coated granule Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000005824 corn Nutrition 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
- 125000006622 cycloheptylmethyl group Chemical group 0.000 description 1
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical class O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000006623 cyclooctylmethyl group Chemical group 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000035613 defoliation Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-O di(propan-2-yl)azanium Chemical compound CC(C)[NH2+]C(C)C UAOMVDZJSHZZME-UHFFFAOYSA-O 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- CKQQMPJQZXIYMJ-UHFFFAOYSA-L dichloride;dihydrate Chemical compound O.O.[Cl-].[Cl-] CKQQMPJQZXIYMJ-UHFFFAOYSA-L 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- OMBRFUXPXNIUCZ-UHFFFAOYSA-N dioxidonitrogen(1+) Chemical class O=[N+]=O OMBRFUXPXNIUCZ-UHFFFAOYSA-N 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- FFLYUXVZEPLMCL-UHFFFAOYSA-N ethylchloranuidyl formate Chemical compound CC[Cl-]OC=O FFLYUXVZEPLMCL-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000002532 grape seed extract Nutrition 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 1
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 1
- 125000004995 haloalkylthio group Chemical group 0.000 description 1
- 125000000232 haloalkynyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229940079867 intestinal antiinfectives Sulfonamides Drugs 0.000 description 1
- YBCISJAPWKQOPH-UHFFFAOYSA-N iodoethane Chemical group [CH2]CI YBCISJAPWKQOPH-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M methanoate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
- 125000004718 n-hexylthio group Chemical group C(CCCCC)S* 0.000 description 1
- 125000002412 n-penten-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002504 n-penten-4-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atoms Chemical group N* 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000018343 nutrient deficiency Nutrition 0.000 description 1
- 229940005938 ophthalmologic antiinfectives Sulfonamides Drugs 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-L oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000004322 oxepan-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004274 oxetan-2-yl group Chemical group [H]C1([H])OC([H])(*)C1([H])[H] 0.000 description 1
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N p-xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 150000008048 phenylpyrazoles Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L phosphate Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000003032 phytopathogenic Effects 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
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 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
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- XNOUKSCKJOEFNJ-UHFFFAOYSA-N prop-2-ene-1-sulfinate Chemical group [O-]S(=O)C[C+]=C XNOUKSCKJOEFNJ-UHFFFAOYSA-N 0.000 description 1
- VQGISNOMGHCEPX-UHFFFAOYSA-N propanenitrile Chemical group C[CH]C#N VQGISNOMGHCEPX-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 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
- 150000004892 pyridazines Chemical class 0.000 description 1
- 125000002098 pyridazinyl 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
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000013526 red clover Nutrition 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000004576 sand Substances 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
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- YOQDYZUWIQVZSF-UHFFFAOYSA-N sodium borohydride Substances [BH4-].[Na+] YOQDYZUWIQVZSF-UHFFFAOYSA-N 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- ODGROJYWQXFQOZ-UHFFFAOYSA-N sodium;boron(1-) Chemical compound [B-].[Na+] ODGROJYWQXFQOZ-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004434 sulfur atoms Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000002195 synergetic Effects 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000001730 thiiranyl group Chemical group 0.000 description 1
- WZMPOCLULGAHJR-UHFFFAOYSA-N thiophen-2-ol Chemical class OC1=CC=CS1 WZMPOCLULGAHJR-UHFFFAOYSA-N 0.000 description 1
- 229940026752 topical Sulfonamides Drugs 0.000 description 1
- 230000001131 transforming Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 235000021307 wheat Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Abstract
The invention relates to 3-(benzazol-4-yl)pyrimidine-dione-derivatives of formula (I) and the salts thereof, whereby X=O, S;R1=H, NH2, C1-C6-alkyl, C1-C6-alkyl halide;R2=H, halogen, C1-C6-alkyl, C1-C6-alkyl halide, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl;R3=H, halogen, C1-C6-alkyl;R4=H, halogen;R5=CN, halogen, C1-C6-alkyl, C1-C6-alkyl halide, C1-C6-alkoxyl, C1-C6-alkoxyl halide;=Y-=a group=N-N(R6)-,=C(ZR7)-N(R6)-,=C(ZR7)-O-,=C(ZR7)-S-;R6=C1-C6-alkyl, C1-C4-alkyl halide, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkyl-SO2, C1-C6-alkyl-CO, C1-C6-alkyl halide-CO, C1-C6-alkyl-CS, C1-C6-alkoxyl-CO, C1-C6-alkoxyl-CS or optionally substituted C1-C6-alkyl;Z=chemical bond, O, S, -S(O)-, -SO2-, -NH-, -N(R8)-;R7, R8=C1-C6-alkyl, C1-C6-alkyl halide, hydroxy-C1-C4-alkyl, cyano-C1-C4-alkyl, C1-C4-alkoxyl-C1-C4-alkyl, C1-C4-alkoxyl halide-C1-C4-alkyl, C3-C4-alkenyloxyl-C1-C4-alkyl, C3-C4-alkynyloxyl-C1-C4-alkyl, C3-C8-cycloalkoxyl-C1-C4-alkyl, amino-C1-C4-alkyl, C1-C4-alkylamino-C1-C4-alkyl, di(C1-C4-alkyl)amino-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-alkylthio halide-C1-C4-alkyl, C3-C4-alkenylthio-C1-C4-alkyl, C3-C4-alkynylthio-C1-C4-alkyl, C1-C4-alkylsulfinyl-C1-C4-alkyl, C1-C4-alkylsulfinyl halide-C1-C4-alkyl, C3-C4-alkenylsulfinyl-C1-C4-alkyl, C3-C4-alkynylsulfinyl-C1-C4-alkyl, C3-C6-alkenyl, cyano-C3-C6-alkenyl, C3-C6-alkenyl halide, C3-C6-alkynyl, cyano-C3-C6-alkynyl, C3-C6-alkynyl halide, HO-CO-C1-C4-alkyl, (C1-C4-alkoxyl)CO-C1-C4-alkyl, (C1-C4-alkyl)CS-C1-C4-alkyl, H2N-CO-C1-C4-alkyl, C1-C4-alkyl-NHCO-C1-C4-alkyl, di(C1-C4-alkyl)NCO-C1-C4-alkyl, di(C1-C4-alkyl)phosphonyl-C1-C4-alkyl, optionally substituted C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl, phenyl-C1-C4-alkyl, 3- to 7-linked heterocyclyl or heterocyclyl-C1-C4-alkyl, whereby each heterocyclyl ring can contain a CO-ring link or CS-ring link, or provided that Z=chemical bond, R7 also H, OH, CN, SH, NH2, halogen, -CH(OH)-CH2-R9, -CH(halogen)-CH2-R9, -CH2-CH(halogen)-R9, -CH=CH-R9 or-CH=C(halogen)-R9, whereby R9=COOH, (C1-C4-alkoxyl)carbonyl, (C1-C4-alkylthio)carbonyl, CONH2, C1-C4-alkyl-NHCO or di(C1-C4-alkyl)NCO, or R7 + R8=an optionally substituted 1,3-propylene-, tetramethylene-, pentamethylene- or ethylene oxyethylene-chain.
Description
Description
The present invention relates to novel 3- (benza-zol-4-yl) pyrimidinedione derivatives of the formula I
in which the variables have the following meanings:
X oxygen or sulfur;
R1 hydrogen, amino, C? -C6-alkyl or Cx-Cd-allogenoalkyl;
R2 hydrogen, halogen, Ci-Cg-alkyl, C6-haloalkyl, Ci-C-alkylthio, C6-alkylsulfinyl or C6-alkylsulphinyl;
R3 hydrogen, halogen or C? -C6 alkyl;
R4 hydrogen or halogen;
R5 cyano, halogen, C? -C6-alkyl, Cx-Cg-haloalkyl, C? -C6-alkoxy or Ci-Cg-halogenoalkoxy;
= Y- one group = N-N (R6) -, = C (ZR7) -N (R6) -, = C (ZR7) -0- or = C (ZR7) -S-;
R6 C? -C6-alkyl, C? -C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C? -C6-alkylsulfonyl, (C? -C6-alkyl) carbonyl, (Ci-Cβ-alkoalkyl) carbonyl, (Ci-Cß-alkyl) thiocarbonyl, (C?-C6-alkoxy) carbonyl, (C?-C6-alkoxy) thiocarbonyl or Ci-Cg-alkyl, which may be substituted by cyano , C? -C6-alkoxy, C? -C6-alkylthio, (C? -C6-alkoxy) carbonyl, (C? -C6-alkylamino) carbonyl, Di (C? -C6-alkyl) aminocarbonyl or (Cx-Ce-alkyl) carbonyloxy;
-N (R8) -;
R7 and R8 each independently of the other, C? -C6-alkyl, C? -C6-haloalkyl, hydroxy-C? -C4-alkyl, cyano-C1-C4-alkyl, C? -C-alkoxy-C? C 4 -alkyl, C 1 -C 4 -halogenoalkoxy-C?-C 4 -alkyl, C 3 -C 4 -alkenyloxy-C 1 -C 4 -alkyl, C 3 -C -alkynyloxy-C?-C 4 -alkyl, C 3 -C 8 -cycloalkoxy -C? -C4-alkyl,
amino-C1-C4-alkyl, C1-C-alkylamino-C? -C4-alkyl, di (C? -C4-alkyl) amino-C? -C -alkyl, C? -C4-alkylthio-C? -C4 -alkyl, C? -C4-haloalkylthio-C? -C4 -alkyl, C3-C4-alkenylthio-C? -C4 -alkyl, C3-C4-alkynylthio-C? -C -alkyl, C? -C- alkylsulfinyl-C? -C4-alkyl, C? -C4-haloalkylsulfinyl-C? -C4-alkyl, C3-C4-alkenylsulfinyl-C? -C -alkyl, C3-C4-alkynylsulfinyl-C? -C4 -alkyl, C? -C4-alkylsulfonyl-C? -C4-alkyl, C? -C4-halogenoalkylsulfonyl-C? -C-alkyl, C3-C4-alkenylsulfonyl-C? -C4-alkyl, C3-C- alkynylsulfonyl-C-C4-alkyl, C3-C6-alkenyl, cyano-C-C6-alkenyl, C-C6-halo-alkenyl, C3-C6-alkynyl, cyano-C3-C6-alkynyl, C3-C6-haloalkynyl, hydroxycarbonyl-C? -C4-alkyl, (C? -C4-alkoxy) carbonyl-C? -C4-alkyl, (C? -C4-alkylthio) carbon-C? -C4-alkyl, aminocarbonyl-C? C4-alkyl, (C? -C4-alkylamino) carbonyl-C? -C4-alkyl, di (C? -C4-alkyl) aminocarbonyl-C? -C4-alkyl, di (C? -C4-alkyl) phosphonyl-C? -C4-alkyl, C3-C8-cycloalkyl, C3-C8-cyc C 4 -C 4 alkyl, phenyl, C 4 -C 4 alkyl, 3 to 7 membered heterocyclyl or heterocyclyl C 1 -C 4 alkyl, each heterocyclyl ring can contain a carbonyl or thiocarbonyl ring member , and each cycloalkyl, phenyl and heterocyclyl ring being unsubstituted or carrying one to four substituents, each selected from the group comprising cyano, nitro, amino, hydroxy, carboxy, halogen, C? -C4-alkyl, C? C -halogenalkyl, C?-C4-alkoxy, C?-C4-haloalkoxy, C?-C4-alkylthio, C?-C4-haloalkylthio, C?-C-alkylsulphinyl, C?-C4-haloalkylsulfonyl, (C C4-alkoxycarbonyl, (C? -C4-alkyl) carbonyl, (C? -C-haloalkyl) carbonyl, (C? -C4-alkyl) carbonyloxy, (C? -C4-haloalkyl) carbonyloxy and di ( C? -C4-alkyl) amino,
or, whenever Z means a chemical bond, R7 can mean, if desired, also hydrogen, hydroxy, cyano, mercapto, amino, halogen, -CH (OH) -CH2-R9, CH = C (halogen) -R9 , where
R9 means hydroxycarbonyl, (C? -C4-alkoxy) carbonyl, (C? -C4-alkylthio) carbonyl, aminocarbonyl, (C? -C4-alkylamino) carbonyl or di (C? -C-alkyl) aminocarbonyl,
or R7 and R8 together form a chain of 1,3-propylene, tetramethylene, penta ethylene or ethyleneoxyethylene, which may in each case be unsubstituted or carry from one to four C? -C4-alkyl groups or one or two groups (C? -C4-alkoxy) carbonyl;
as well as the salts useful in the agriculture of the compounds I.
In addition, the invention relates to the use of the compounds I as herbicides, to herbicidal products, which contain the compounds I as active substances, to processes for the preparation of the compounds I and of the herbicidal products using the compounds I. - to processes for combating the growth of undesired plants with the compounds I, as well as - to intermediate products of the formulas III, IV and V for obtaining the compounds I.
In WO 97/08170 certain 3- (benz (ox / ti) azol-7-yl) -6- (trifluoromethyl) -uracils are described as herbicides. Other 3- (benz-thiazol-7-yl) uracils, as well as their use as herbicides and for the desiccation / defoliation of plants are taught in WO 97/08171. The subject of WO 97/12886 are, among other substances, certain 3-benzisoxazol-7-yl-2,4- (lH, 3H) pyrimidinediones, to which a herbicidal and desiccant action is attributed.
The present invention has for its object to provide new uracil compounds with herbicidal action, which allow to fight better and more specifically against undesired plants, than with the known products.
Thus, the present 3- (benza-zol-4-yl) pyrimidinedione derivatives of the formula I were found.
In addition, herbicidal products were found, which contain the compounds I and which have a very good herbicidal action. Additionally, methods for obtaining these compounds and methods for controlling the growth of unwanted plates with compounds I were found.
One or more substances which are present as enantiomeric or diastereomeric mixtures are present. Both the enantiomers or putative diastereomers and their mixtures are subject of the present invention.
For some compounds of the invention, their general formula I represents only one of the possible forms of writing. For example, those compounds with R7 = hydroxy can also be screened with I 'tautomers [-N = C (0H) - < - * - NH-CO-]:
Useful salts in agriculture are understood above all to be the salts of those cations or the acid addition salts of those acids whose cations or anions do not negatively affect the herbicidal effect of the compounds I. Thus, as cations they are especially appropriate the ions of the alkali metal salts, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and the salts of transition metals, preferably manganese, copper, zinc and iron, as well as the ammonium anion, which, if desired, it can carry one to four C? -C4 alkyl substituents and / or a phenyl or benzyl substituent, and, if desired, additionally from one to three additional alkyl radicals having 1 to 4 carbon atoms, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, in addition, the phosphonium ions, preferably, tri- (C? -C4-alkyl) -phosphonium, sulfoxonium ions, preferably tri (C? -C4-a) lquil) sulfoxonium.
The anions of suitable acid addition salts are, first, chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, hexafluorosilicate carbonate, hexafluorosate, benzoate, oxalate, dodecylbenzenesulfonate, as well as anions of alkanoic acids with 1 to 4 carbon atoms, preferably the formate, acetate, propionate and butyrate. They can be formed by reacting I with a corresponding anion acid, preferably phosphoric acid and nitric acid.
The organic molecule parts mentioned in the definition of the substituents R1 to R3 and R5 to R9 or as radicals in the cycloalkyl, phenyl or heterocyclic rings represent - the same as the meaning of halogen - collective terms for the individual enumeration of the different members of group. All carbon chains, namely all alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, aminoalkyl, hydroxycarbonylalkyl, aminocarbonylalkyl, phenylalkyl, heterocyclyloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulphonyl, alkenyl, haloalkenyl, cyanoalkenyl, alkenyloxy, alkenylthio, alkenylsulfinyl, alkenylsulfonyl, alkynyl, haloalkynyl, cyanoalkynyl, alkynyloxy, alkynylthio, alkynylsulfinyl and alkynylsulfonyl can be linear or branched. The halogenated substituents preferably have one to five identical or different halogen atoms. Halogen means each time fluorine, chlorine, bromine or iodine.
In addition, they mean, for example:
- C -C 4 -alkyl: CH 3, C 2 H 5, CH 2 -C 2 H 5, CH (CH 3) 2, n-butyl, CH (CH 3) -C 2 H 5, CH -CH (CH 3) 2 or C (CH 3) 3;
- C? -C4-halogenoalkyl: a C? -C4-alkyl radical such as those mentioned above, which may be partially or completely substituted by fluoro, chloro, bromo and / or iodo, ie, eg CH2F, CHF2,
CF3, CH2C1, CH (C1) 2, C (C1) 3, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 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, C2Fs, 2-fluoropropyl, 3- fluoropropyl, 2, 2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3, 3, 3-trifluoropropyl, 3,3,3- trichloropropyl, CH2-C2F5, CF2-C2F5, 1- (fluoromethyl) -2-fluoroethyl, 1- (chloromethyl) -2-chloroethyl, 1- (bromomethyl) -2-bromoethyl, 4-fluorobutyl, 4- chlorobutyl, 4-bromobutyl or nonafluorobutyl;
- C? -C6-alkyl: a C? -C4-alkyl radical such as those mentioned above, or, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2.2-? dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpen-1,2-d-methylbutyl, 1,3-d-meth, , - me uo, 2, 3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl, preferably CH 3, C 2 H 5, CH 2 -C 2 H 5, CH (CH 3) 2, n-butyl, C (CH 3) 3, n-pentyl or n-hexyl;
- C6C6-halogenoalkyl: a C6C6-alkyl radical such as those mentioned above, which may be partially or completely substituted by fluoro, chloro, bromo and / or iodo, ie, eg one of the radicals mentioned for C?-C4-halogenoalkyl Genannten Substance or für 5-fluoro-l-pentyl, 5-chloro-l-pentyl, 5-bromo-l-pentyl, 5-iodo-l-pentyl, 5,5,5- trichloro-l-penyl, undecafluoropentyl, 6-fluoro-1-hexyl, 6-chloro-l-hexyl, 6-bromo-l-hexyl, 6-iodo-l-hexyl, 6,6,6-trichloro-l- hexyl or dodecafluorohexyl;
- cyano-C? -C4-alkyl: CH2CN, 1-cyanoethyl, 2-cyanoethyl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3-cyanopropyl-1-yl, 1-cyano- but-1-yl, 2-cyanobut-1-yl, 3-cyanobut-1-yl, 4-cyanobut-1-yl, l-cyanobut-2-yl, 2-cyanobut-2-yl, 3- cyanobut-2-yl, 4-cyanobut-2-yl, l- (CH 2 CN) et-1-yl, l- (CH 2 CN) -l- (CH 3) -et-1-yl or l- (CH 2 CN) prop-l-ilo;
- hydroxy-C? -C4-alkyl: CH20H, 1-hydroxyethyl, 2-hydroxyethyl,
1-hydroxyprop-1-yl, 2-hydroxyprop-1-yl, 3-hydroxyprop-1-yl, 1-hydroxybutyl-1-yl, 2-hydroxybutyl-1-yl, 3-hydroxybutyl-yl, 4- hydroxybutyl-1-yl, 1-hydroxybut-2-yl, 2-hydroxybut-2-yl, 3-hydroxybut-2-yl, 4-hydroxybut-2-yl, 1- (CHOH) et-1-yl, 1- (CH 2 OH) -l- (CH 3) -et-l-yl or l- (CH 2 OH) prop-1-yl;
C-C-C4-alkyl: CH2NH, 1-aminoethyl, 2-aminoethyl, 1-aminoprop-1-yl, 2-aminoprop-1-yl, 3-aminoprop-1-yl, 1-amino-butyl -1-yl, 2-aminobut-l-yl, 3-aminobut-l-yl, 4-amino-but-1-yl, l-aminobut-2-yl, 2-aminobut-2-yl, 3-amino - but-2-yl, 4-amino-but-2-yl, l- (CH2NH2) et-l-yl, l- (CH2NH2) -l- (CH3) -et-l-yl or 1- (CH2NH2 ) prop-l-ilo;
- hydroxycarbonyl-C? -C4-alkyl: CH2C00H, l- (C00H) ethyl, 2- (COOH) ethyl, l- (COOH) prop-l-yl, 2- (COOH) prop-l-yl, 3- (C00H) -prop-l-yl, l- (C00H) but-l-yl, 2- (C00H) but-l-yl, 3- (C00H) but-l-yl, 4- (C00H) but- l -yl, l- (COOH) but-2-yl, 2- (COOH) but-2-yl, 3- (COOH) but-2-yl, 4- (COOH) but-2-yl, l- (CH2C00H) et-l-yl, l- (CH2COOH) -l- (CH3) -et-l-yl or l- (CH2COOH) prop-l-yl;
2- (CONH) et lo, l- (CONH2) prop- - o, - 2 prop- - o, 3- (CONH2) prop-l-yl, l- (CONH2) but-l-yl, 2- ( CONH2) but-l-yl, 3- (CONH2) but-l-yl, 4- (CONH2) but-l-il ?, l- (CONH2) but-2-yl, 2- (CONH2) but-2 -yl, 3- (CONH2) but-2-yl, 4- (CONH2) but-2-yl, l- (CH2CONH2) et-l-yl, l- (CH2CONH2) -1- (CH3) -et- 1-yl or 1- (CH2C0N-H2) prop-1-yl;
- phenyl-C? -C4-alkyl: benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenylprop-1-yl, 1-phenyl- but-1-yl, 2-phenylbut-l-yl, 3-phenylbut-l-yl, 4-phenyl-but-1-yl, l-phenylbut-2-yl, 2-phenylbut-2-yl, 3- phenyl-but-2-yl, 4-phenylbut-2-yl, 1- (benzyl) -et-l-yl, l- (benzyl) -l- (methyl) -et-l-yl or l- (benzyl) -prop-1-yl, preferably benzyl or 2-phenylethyl;
- heterocyclyl-C? -C4-alkyl: heterocyclylmethyl, 1-heterocyclyl-ethyl, 2-heterocyclyl-ethyl, 1-heterocyclyl-prop-1-yl, 2-heterocyclyl-prop-1-yl, 3-heterocyclyl- prop-l-yl, 1-heterocyclyl-but-1-yl, 2-heterocyclyl-but-l-yl, 3-heterocyclyl-but-l-yl, 4-heterocyclyl-but-l-yl, l-heterocyclyl- but-2-yl, 2-heterocyclyl-but-2-yl, 3-heterocyclyl-but-2-yl, 3-heterocyclyl-but-2-yl, 4-heterocyclyl-but-2-yl, l- (heterocyclylmethyl) -et-1-yl, 1- (heterocyclylmethyl) -l- (methyl) -et-1-yl or 1- (heterocyclylmethyl) -prop-1-yl, preferably heterocyclylmethyl or 2-heterocyclyl -ethyl;
C -C4-alkoxy for: 0CH3, OC2H5, OCH2-CH5, OCH (CH3) 2, n-butoxy, OCH (CH3) -C2H5, OCH2-CH (CH3) 2 or C (CH3) 3, preferably 0CH3, OC2H5 O OCH (CH3) 2;
- C? -C4-halogenoalkoxy: a C? -C4-alkoxy radical such as those mentioned above, which is partially or completely substituted by fluoro, chloro, bromo and / or iodo, viz., Eg 0CH2F, OCHF2, OCF3 , 0CH2C1, OCH (Cl) 2, 0C (C1) 3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy, 2, 2, 2-trifluoroethoxy , 2-chloro-2-fluoroethoxy, 2-chloro-2, 2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2, 2,2-trichloroethoxy, OC2Fs, 2-fluoropropoxy, 3-fluoropropoxy , 2, 2-difluoropropoxy, 2, 3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3, 3, 3-trifluoropropoxy, 3,3,3 -trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1- (CH2F) -2-fluoroethoxy, l- (CH2Cl) -2-chloroethoxy, l- (CH2Br) -2-bromoethoxy, 4-fluoro-butoxy, 4-chlorobutoxy , 4-bromobutoxy or nonafluorobutoxy, prefetoxy or 2,2,2-trifluoroethoxy;
C? -C6-alkoxy: a C? -C4-alkoxy radical such as those mentioned above, or for example n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methyl-butoxy, 2,2-dimethylpropoxy, -ethylpropoxy, n-hexoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethyl-butoxy , 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-tri-methylpropoxy, 1,2,2 -trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy, preferably OCH 3, OC 2 H 5, OCH 2 -C 2 H 5, OCH (CH 3) 2, n-butoxy, OC (CH 3) 3, n-pentoxy or n- hexoxi;
C? -C6-halogenoalkoxy: a C? -C6-alkoxy radical such as those mentioned above, which may be partially or completely substituted by fluoro, chloro, bromo and / or iodo, namely, for example, one of the radicals mentioned for C? -C4-halogenoalkoxy or for 5-fluoro-l-pentoxy, 5-chloro-l-pentoxy, 5-bromo-l-pentoxy, 5-iodo-l-pentoxy, 5,5,5-trichloro-l -pentoxy, undecafluoropen-toxi, 6-fluoro-1-hexoxy, 6-chloro-1-hexoxy, 6-bromo-1-hexoxy, 6-iodo-1-hexoxy, 6,6-trichloro-1-hexoxy or dsdecafluorohexoxi;
C? -C -alkylthio: SCH3, SC2H5, SCH2-C2H5, SCH (CH3) 2, n-butylthio, SCH (CH3) -C2H5, SCH2-CH (CH3) 2 or SC (CH3) 3, preferably SCH3 or SC2H5;
C? -C4-haloalkylthio: a C? -C4-alkylthio radical such as those mentioned above, which is partially or completely substituted by fluoro, chloro, bromo and / or iodo, namely, eg SCH2F, SCHF2, SCF3, SCH2C1, SCH (C1) 2, SC (Cl) 3, chlorofluoromethylthio, dichloro-fluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2, 2, 2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, SC2F5, 2-fluoropropylthio, 3-fluoropro- pylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2-chloro-propylthio, 3-chloropropylthio, 2,3-dichloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio, 3, 3,3-tri-chloropropylthio, SCH2-C2F5, SCF2-C2F5, 1- (CH2F) -2-fluoroethylthio, 1- (CH2Cl) -2-chloroethylthio, 1- (CH2Br) -2-bromoethylthio, 4-fluorobu- tiltium, 4-chlorobutylthio, 4-bromobutylthio or SCF -CF2-C2F5, preferably SCHF2, SCF3, dichlorofluoromethylthio, chlorodifluoromethylthi or or 2, 2, 2-trifluoroethylthio;
c onados, or e. n-pent t o, -met u t o, -me u-thio, 3-methylbutylthio, 2, 2-dimethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpenthylthio, 1,1-dimethylbutylthio, 1,2 dimethyl butylthio, 1,3-dimethyl butylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1-trimethylpro-pylthio, 1 , 2,2-trimethylpropylthio, 1-ethyl-l-methylpropylthio or l-ethyl-2-methylpropylthio, preferably SCH3, SC2H5, SCH-C2H5, SCH (CH3) 2, n-butylthio, SC (CH3) 3, n- pentthylthio or n-hexylthio;
C 4 -C-alkoxy-C 1 -C 4 -alkyl: C 1 -C 4 -alkyl substituted by C 4 -C-alkoxy -as the above-mentioned, namely, eg für CH 2 -OCH 3, CH 2 -CH 2 H 5 , n-propoxymethyl, CH2-OCH (CH3) 2, n-butoxymethyl, (1-methylpropoxy) methyl, (2-methylpropoxy) methyl, CH2-OC (CH3) 3, 2- (methoxy) ethyl, 2- (ethoxy) ethyl, 2- (n-pro-poxy) ethyl, 2- (1-methylethoxy) ethyl, 2- (n-butoxy) ethyl, 2- (1-methylpropoxy) ethyl, 2- (2- methylpropoxy) ethyl, 2- (1,1-di-ethyl-toxy) ethyl, 2- (methoxy) propyl, 2- (ethoxy) propyl, 2- (n-pro-poxy) propyl, 2- (1-methylethoxy) ) propyl, 2- (n-butoxy) -propyl, 2- (1-methylpropoxy) propyl, 2- (2-methylpropoxy) ropyl, 2- (1, 1-dimethylethoxy) propyl, 3- (methoxy) propyl, - (ethoxy) -propyl, 3- (n-propoxy) propyl, 3- (1-methylethoxy) propyl, 3- (n-bu-toxy) propyl, 3- (1-methylpropoxy) ropyl, 3- (2- methylpropoxy) pro-phenyl, 3- (1,1-dimethylethoxy) propyl, 2- (methoxy) butyl, 2- (ethoxy) butyl, 2- (n-propoxy) butyl, 2- (1-methylethoxy) butyl, - (n-butoxy) butyl, 2- (l-methylpropoxy) butyl, 2- (2-methylpro-poxy) butyl, 2- (1, 1- dimethylethoxy) butyl, 3- (methoxy) butyl, 3- (ethoxy) butyl, 3- (n-propoxy) butyl, 3- (1-methylethoxy) butyl, 3- (n-butoxy) util, 3- (1- methylpropoxy) butyl, 3- (2-methylpro-poxy) butyl, 3- (1,1-dimethylethoxy) butyl, 4- (methoxy) butyl, 4- (ethoxy) butyl, 4- (n-propoxy) butyl, - (1-methylethoxy) butyl, 4- (n-butoxy) butyl, 4- (1-methylpropoxy) butyl, 4- (2-methylpro-poxy) butyl or 4- (1, 1-dimethylethoxy) butyl, preferably CH 2 -OCH3, CH2-OC2H5, 2- (0CH3) ethyl or 2- (OC2H5) ethyl;
C? -C4-halogenoalkoxy-C? -C4-alkyl: C? -C4-alkyl substituted by C? -C -haloalkoxy as the above-mentioned, viz. ex. 2- (OCHF2) ethyl, 2- (OCF3) ethyl or 2- (OC2F5) ethyl;
C? -C4-alkylthio-C? -C -alkyl: C? -C4-alkyl substituted by C? -C4-alkylthio- as mentioned above - namely, eg CH2-SCH3, CH2-SC2H5, n-propylthiomethyl, CH2-SCH (CH3) 2, n-butyl-thiomethyl, (l-methylpropylthio) methyl, (2-methylpropylthio) methyl, CH2-SC (CH3) 3, 2- (methylthio) ethyl, 2- ( ethylthio) -ethyl, 2- (n-pro-pylthio) ethyl, 2- (l-methylethylthio) ethyl, 2- (n-butylthio) ethyl, 2- (l, l-dimethylethyl) o lo, 2- ( met to) prop or, - e -thio) propyl, 2- (n-propylthio) propyl, 2- (1-methylethylthio) propyl, 2- (n-butylthio) propyl, 2- (1-methylpropylthio) propyl, - (2-methyl-propylthio) ropyl, 2- (1,1-dimethylethylthio) ropyl, 3- (methyl-thio) propyl, 3- (ethylthio) propyl, 3- (n-propylthio) propyl, 3- (1 -methylethylthio) propyl, 3- (n-butylthio) propyl, 3- (l-methyl-propylthio) -propyl, 3- (2-methylpropylthio) propyl, 3- (1,1-dimethyl-ethylthio) propyl, 2- (methylthio) butyl, 2- (ethylthio) butyl, 2- (n-propylthio) butyl, 2- (1-methylethylthio) butyl, 2- (n-butylthio) butyl, 2- (1-methylpropylthio) butyl, 2- (2-methylpropylthio) buti lo, 2- (1, 1-dimethylethylthio) butyl, 3- (methylthio) butyl, 3- (ethylthio) butyl, 3- (n-propylthio) butyl, 3- (1-methylethylthis) butyl, 3-. { n-butylthio) butyl, 3- (1-methylpropylthio) butyl, 3- (2-methylpropylthio) butyl, 3- (1,1-dimethylethylthio) butyl, 4- (methylthio) butyl, 4- (ethylthio) butyl, - (n-propylthio) butyl, 4- (l-methylethylthio) butyl, 4- (n-butylthio) -butyl, 4- (1-methylpro-pylthio) butyl, 4- (2-methylpropylthio) utilo or 4- ( 1, 1-dimethylethylthio) butyl, preferably CH2-SCH3, CH2-SC2H5, 2- (SCH3) ethyl or 2- (SC2H5) ethyl;
C?-C4-haloalkylthio-C?-C4-alkyl: C?-C4-alkyl substituted by C?-C4-haloalkylthio as the above-mentioned, namely, eg 2- (SCHF 2) ethyl, 2- ( SCF3) ethyl or 2- (SC2F5) ethyl;
(C? -C4-alkyl) carbonyl: C0-CH3, C0-C2H5, CO-CH2-C2H5, CO-CH (CH3) 2, n-butylcarbonyl, CO-CH (CH3) -C2H5, CO-CH2-CH (CH3) 2 < CO-C (CH3) 3, preferably C0-CH3 or CO-C H5;
(C? -C4-haloalkyl) carbonyl: a radical (C? -C-alkyl) carbonyl - such as those mentioned above - which is partially or completely substituted by fluoro, chloro, bromo and / or iodo, viz. C0-CH2F, C0-CHF2, C0-CF3, C0-CH2C1, C0-CH (C1) 2, C0-C (C1) 3, chlorofluoromethylcarbonyl, dichlorofluoroethylcarbonyl, chloro-difluoromethylcarbonyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl bonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2, 2-difluoroethylcarbonyl, 2, 2, 2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2,2-difluoroethylcarbonyl, 2,2-di-chloro-2-fluoroethylcarbonyl, 2,2,2-trichloroethylcarbonyl, CO-C2F5, 2 -fluoropropylcarbonyl, 3-fluoropropylcarbonyl, 2,2-difluoropropylcarbonyl, 2,3-difluoropropylcarbonyl, 2-chloropropylcarbonyl, 3-chloropropylcarbonyl, 2,3-dichloropropylcarbonyl, 2-bromopropylcarbonyl, 3-bromopropylcarbonyl, 3,3,3-trifluoropropylcarbonyl , 3,3, 3-trichloropropylcarbonyl, CO-CH2-C2F5, CO-CF2-C2F5, 1- (CH2F) -2-fluoroethylcarbonyl, 1- (CH2Cl) -2-chloroethylcarbonyl, 1- (CH2Br) -2-bromoethylcarbonyl , 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcar-CO-CH2Cl or 2, 2, 2-trifluoroethylcarbonyl;
(C? -C6-alkyl) carbonyl: one of the above-mentioned radicals (C? -C-alkyl) -carbonyl, or, for example, n-pentyl-CO, 1-methylbutyl-CO, 2-methylbutyl-CO , 3-methylbutyl-CO, 2, 2-dimethylpropyl-CO, 1-ethylpropyl-CO, n-hexyl-CO, 1,1-dimethylpropyl-CO, 1,2-dimethyl-propyl-CO, 1-methylpentyl-CO , 2-methylpentyl-CO, 3-methylpentyl-CO, 4-methylpentyl-CO, 1, 1-dimethylbutyl-CO, 1, 2-dimethylbutyl-CO, 1,3-dimethylbutyl-CO, 2,2-dimethylbutyl-CO , 2, 3-dimethylbutyl-CO, 3,3-dimethylbutyl-CO, 1-ethylbutyl-CO, 2-ethylbutyl-CO, 1,1,2-tri-methylpropyl-CO, 1,2,2-trimethylpropyl-CO , 1-ethyl-l-methylpropyl-CO or l-ethyl-2-methylpropyl-C0, preferably CO-CH3, CO-C2H5, CO-CH2-C2H5, CO-CH (CH3) 2, n-butyl-CO, CO-C (CH3) 3, CO- (n-C5H ??) or CO- (n-C6H? 3);
(C? -C6-haloalkyl) carbonyl: a (C? -C6-alkyl) carbonyl radical - such as those mentioned above - which is partially or completely substituted by fluoro, chloro, bromo and / or iodo, viz. C0-CH2F, C0-CHF2, C0-CF3, C0-CH2C1, C0-CH (C1) 2, CO-C (Cl) 3, chlorofluoromethylcarbonyl, dichlorofluoromethylcarbonyl, chlorodifluoromethylcarbonyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, -bromoethylcarbonyl, 2-iodoethylcarbonyl, 2,2-difluoroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2,2-difluoroethylcarbonyl, 2,2-di-chloro-2-fluoroethylcarbonyl , 2,2, 2-trichloroethylcarbonyl, CO-C2F5, 2-fluoropropylcarbonyl, 3-fluoropropylcarbonyl, 2,2-difluoropropylcarbonyl, 2,3-difluoropropylcarbonyl, 2-chloropropylcarbonyl, 3-chloropropylcarbonyl, 2,3-dichloropropylcarbonyl, 2 -bromopropylcarbonyl, 3-bromopropylcarbonyl, 3, 3, 3-trifluoropropylcarbonyl, 3,3, 3-trichloropropylcarbonyl, CO-CH2-C2F5, CO-CF2-C2F5, 1- (CH2F) -2-fluoroethylcarbonyl, 1- (CH2C1) -2-chloroethylcarbonyl, 1- (CH2Br) -2-bromoethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl or nonafluorobutylcarbonyl, preferably C0-CF3CO-CH2Cl or 2,2,2-trifluoroethylcarbonyl;
(C1-C4-alkyl) carbonyloxy: 0-C0-CH3, 0-CO-C2H5, 0-CO-CH2-C2H5, 0-CO-CH (CH3) 2, 0-CO-CH2-CH2-C2H5, O -CO-CH (CH3) -C H5, O-CO-CH2-CH (CH3) 2 or 0-CO-C (CH3) 3, preferably 0-C0-CH3 or 0-CO-C2H5;
(C? -C4-haloalkyl) carbonyloxy: a radical (C? -C-alkyl) carbonyl - as mentioned above - which is partially or completely substituted by fluoro, chloro, bromo and / or iodo, viz. .ej. 0-CO-CH2F, 0-CO-CHF2, 0-CO-CF3, 0-CO-CH2Cl, 0-CO-CH (Cl) 2, 0-C0-C (Cl) 3, chlorofluoromethylcarbonyloxy, dichlo - - luoroet lcar on ox, -c oroe car on ox, - romoe -carbonyloxy, 2-iodoethylcarbonyloxy, 2,2-difluoroethylcarbonyloxy, 2,2,2-trifluoroethylcarbonyloxy, 2-chloro-2-fluoroethylcarbonyloxy, -chloro-2, 2-difluoroethylcarbonyloxy, 2,2-di-chloro-2-fluoroethylcarbonyloxy, 2,2,2-trichloroethylcarbonyloxy, 0-CO-C2F5, 2-fluoropropylcarbonyloxy, 3-fluoropropylcarbonyloxy, 2,2-difluoropropylcarbonyloxy , 2, 3-difluoropropylcarbonyloxy, 2-chloropropylcarbonyloxy, 3-chloropropylcarbonyloxy, 2,3-dichloropropylcarbonyloxy, 2-bromopropylcarbonyloxy, 3-bro-mo-propylcarbonyloxy, 3,3,3-trifluoropropylcarbonyloxy, 3,3,3-trichloropropylcarbonyloxy, 0-CO -CH2-C2F5, 0-CO-CF2-C2F5, 1- (CH2F) -2-fluoroethylcarbonyl oxy, 1- (CH2C1) -2-chloroethylcarbonyloxy, 1- (CH2Br) -2-bromoethylcarbonyloxy, 4-fluorobutylcarbonyloxy, 4-chlorobutylcarbonyloxy, 4-bromobutylcarbonyloxy or nona-fluorobutylcarbonyloxy, preferably 0-C0-CF3, 0-CO -CH2Cl or 2,2, 2-trifluoroethylcarbonyloxy;
(C? -C6-alkyl) carbonyloxy: one of the above-mentioned radicals (C? -C4-al-quil) carbonyloxy, or, for example, n-pentyl-COO,
1-methylbutyl-COO, 2-methylbutyl-C00, 3-methylbutyl-COO, 2,2-dimethyl-propyl-COO, 1-ethylpropyl-COO, n-hexyl-COO, 1,1-dimethylpro-pil-COO, 1,2-dimethylpropyl-COO, 1-methylpentyl-COO, 2-methylpen-tyl-COO, 3-methylpentyl-COO, 4-methylpentyl-COO, 1,1-dimethylbutyl-COO, 1,2-dimethylbutyl- COO, 1,3-dimethylbutyl-COO, 2,2-dimethyl-butyl-COO, 2,3-dimethylbutyl-COO, 3,3-dimethylbutyl-COO, 1-ethylbutyl-COO, 2-ethylbutyl-COO, 1, 1,2-trimethylpropyl-COO, 1,2,2-trimethylpropyl-COO, 1-ethyl-l-methylpropyl-COO or l-ethyl-2-methylpropyl-C00, preferably 0-CO-CH3, 0-CO-C2H5 , 0-CO-CH2-C2H5, 0-CO-CH (CH3) 2, n-butyl-COO, 0-CO-C (CH3) 3, 0-C0- (n-C5H?) Or 0-CO- (n-C6H? 3);
(C? -C6-alkyl) thiocarbonyl: CS-CH3, CS-C2H5, CS-CH2-C2H5, CS-CH (CH3) 2, CS- (n-C4H9), CS-CH (CH3) -C2H5, CS -CH2-CH (CH3) 2, CS-C (CH3) 3, CS- n-CsHx), CS-CH (CH3) -CH2-C2H5, CS-CH2-CH (CH3) -C2H5, CS-CH CH2 -CH (CH3) 2, CS-C (CH3) 2-C2H5, CS-CH (CH3) -CH (CH3) 2, CS-CH2-C (CH3) 3, CS-CH (C2H5) -C2H5, CS - (n-C6H13), CS-CH (CH3) - (n-C4H9), CS-CH2-CH (CH3) -CH2-C H5, CS-CH2CH2-CH (CH3) -C H5, CS-CH2CH2CH2- CH (CH3) 2, CS-C (CH3) 2-CH2-C2H5, CS-CH (CH3) -CH (CH3) -C2H5, CS-CH (CH3) -CH2-CH (CH3) 2, CS-CH2 -C (CH3) 2-C2H5, CS-CH2-CH (CH3) -CH (CH3), CS-CH2CH2-C (CH3) 3, CS-CH (C2H5) -CH2-C2H5, CS-CH-CH ( C2H5) -C2H5, CS-C (CH3) 2-CH (CH3) 2, CS-CH (CH3) -C (CH3) 3, CS-C (CH3) (C2H5) -C2H5 or CS-CH (C2H5) -CH (CH3) 2, preferably CS-CH3, CS-C2H5, CS-CH2-C2H5 / CS-CH (CH3) 2 O CS- (n-C4H9);
C -OCH CH 3) 2, n-butoxy car on or, - 3 - 2 5, CO-OCH 2 -CH (CH 3) 2 or CO-OC (CH 3) 3, preferably CO-OCH 3 or C 0 - OC 2 H 5;
- (C? -C6-alkoxy) carbonyl: one of the above-mentioned radicals (C? -C4-alkoxy) carbonyl, or, for example, n-pentoxy-CO, 1-methylbutoxy-CO, 2-methylbutoxy-? CO, 3-methylbutoxy-CO, 2,2-dimethylpropoxy-CO, 1-ethylpropoxy-CO, n-hexoxy-CO, 1,1-dimethylpropoxy-CO, 1,2-dimethylpropoxy-CO, 1-methylpentoxy- CO, 2-methylpentoxy-CO, 3-methyl-pentoxy-CO, 4-methylpentoxy-C0, 1, 1-dimethylbutoxy-CO, 1,2-dimethylbutoxy-CO, 1,3-dimethylbutoxy-CO, 2, 2-dimethylbutoxy-CO, 2,3-dimethylbutoxy-CO, 3,3-dimethylbutoxy-CO, 1-ethylbutoxy-CO, 2-ethylbutoxy-C0, 1, 1, 2-trimethylpropoxy-C0, 1,2,2- trimethylpropoxy-CO, 1-ethyl-l-methylpropoxy-CO or l-ethyl-2-methylpropoxy-CO, preferably C0-0CH3, CO-OC2H5 / CO-OCH2-C2H5, CO-OCH (CH3) 2, n -butoxy-CO, CO-OC (CH3) 3, n-pentoxy-CO or n-hexoxy-CO;
- (C? -C4-alkoxy) carbonyl-C? -C4-alkyl: C? -C4-alkyl substituted by (C? -C4-alkoxy) -carbonyl - as mentioned above - namely, eg. CH2-CO-OCH3, CH2-CO-OC2H5, CH2-CO-OCH2-C2H5, CH2-CO-OCH (CH3) 2, n-butoxycarbonylmethyl, CH2-CO-OCH (CH3) -C2H5, CH2-C0-OCH2 -CH (CH3) 2, CH2-CO-OC (CH3) 3, 1- (CO-OCH3) ethyl, l- (CO- 0C2H5) ethyl, l- (CO-OCH2-C2H5) ethyl, 1- [CH (CH3) 2] ethyl, l- (n-butoxycarbonyl) ethyl, l- [1-methylpropoxycarbonyl] ethyl, l- [2-methylpropoxycarbonyl] ethyl, 2- (CO-OCH3) ethyl, 2- ( CO-OC2H5) ethyl, 2- (CO-OCH2-C2H5) ethyl, 2- [CO-OCH (CH3) 2 Jetyl, 2- (n-butoxycarbonyl) ethyl, 2- [1-methylpropoxycarbonyl-Jetyl, 2- [2-methylpropoxycarbonyl] ethyl, 2- [CO-OC (CH3) 3 Jetyl, 2- (CO-OCH3) propyl, 2- (CO-OC2H5) propyl, 2- (CO-OCH2-C2H5) propyl? , 2- [C0- OCH (CH) 2 J-propyl, 2- (n-butoxycarbonyl) ropyl, 2- [1-methylpropoxycarbonyl] propyl, 2- [2-methylpropoxycarbonyl] propyl, 2- [CO- OC (CH3 ) 3 Jpropyl, 3- (CO-OCH3) -propyl, 3- (CO-OC2H5) propyl, 3- (CO-OCH2-C2H5) -propyl, 3- [CO-OCH (CH3) 2 Jpr opyl, 3- (n-butoxycarbonyl Jpropyl, 3- [1-methylpropoxycarbonyl] Jpropyl, 3- [2-methylpropoxycarbonylpropyl], 3- [CO-OC (CH3) 3 J-propyl, 2- (CO-OCH3) butyl, 2- (CO- OC2H5) butyl, 2- (CO-OCH2-C2H5) butyl, 2- [CO-OCH (CH3) 2 J- butyl, 2- (n-butoxycarbonyl) butyl, 2- [1-methylpropoxycarbonylbutyl, 2- [2-methylpropoxycarbonylJbutyl, 2- [C0-OC (CH3) 3Jbutyl, 3- (C0-0CH3) butyl, 3- (CO-OC2H5) butyl, 3- (CO-OCH2-C2H5) butyl, 3- [ CO-OCH (CH3) 2Jbutyl, 3- (n-butoxycarbonyl) butyl, 3- [1-methylpropoxycarbonyl] butyl, 3- [2-methylpropoxycarbonyljbutyl, 3- [CO-OC (CH3) 3Jbutyl, 4- (CO-OCH3) butyl,
4- (CO-OC2H5) butyl, 4- (CO-OCH2-C2H5) butyl, 4- [C0-0CH (CH3) 2 Jbutyl, 4- (n-butoxycarbonyl) butyl, 4- [1-methylpropoxycarbonyl Jbu-] CH2-CO-OCH3, CH2-CO-OC2H5, 1- (C0-0CH3 Jet or 1- (C0-0C2H5 Jetyl;
- (C? -C6-alkoxy) thiocarbonyl: eg CS-0CH3, CS-0C2H5, CS-0CH2-C2H5, CS-0CH (CH3) 2, CS-0 (n-C4H9), CS-OCH ( CH3) -C2H5, CS-0CH2-CH (CH3) 2, CS-0C (CH3) 3, CS-O (n-C5H), CS-OCH (CH3) -CH2-C2H5, CS-OCH2-CH (CH3) -C2H5, CS-0CH2CH2-CH (CH3) 2, C0-0CH2-C (CH3) 3, CS-OCH (C2H5) -C2H5, CS-0 (n-C6H13), CS-OC (CH3) 2-C2H5, CS-OCH (CH3) -CH (CH3) 2, CS-OCH (CH3) - (n-C4H9), CS-0CH2-CH (CH3) -CH2-C2H5, CS-OCH2CH2-CH (CH3 ) -C-H5, CS-OCH2CH2CH2-CH (CH3) 2, CS-OC (CH3) 2-CH2-C2H5, CS-OCH (CH3) -CH (CH3) -C2H5, CS-OCH (CH3) -CH2- CH (CH3) 2, CS-0CH2-C (CH3) 2-C2H5, CS-OCH2-CH (CH3) -CH (CH3) 2, CS-OCH2CH2-C (CH3) 3, CS-OC (C2H5) - CH2-C2H5, CS-OCH2-CH (C2H5) -C2H5, CS-OC (CH3) 2-CH (CH3) 2,
CS-OCH (CH3) -C (CH3) 3, CS-OC (CH3) (C2H5) -C2H5 or CS-OCH (C2H5) -CH (CH3) 2, preferably CS-OCH3 or CS-OC2H5;
- (C? -C4-alkylthio) carbonyl: C0-SCH3, CO-SC2H5, CO-SCH2-C2H5, CO- SCH (CH3) 2, CO-SCH2CH2-C2H5, C0-SCH (CH3) -C2H5, CO- SCH2-CH (CH3) 2 O
CO-SC (CH3) 3, preferably CO-SCH3 or CO-SC2H5;
(C? -C-alkylthio) carbonyl-C? -C4-alkyl: C? -C4-alkyl substituted by (C? -C4-alkylthio) carbonyl - such as those mentioned above, namely, eg CH2- CO-SCH3, CH2-CO-SC2H5, CH2-CO-SCH2-C2H5, CH2-CO-SCH (CH3) 2, CH2-CO-SCH2CH2-C2H5, CH2-CO-SCH (CH3) -C2H5, CH2-CO -SCH2-CH (CH3) 2, CH2-CO-SC (CH3) 3,
1- C0-SCH3) ethyl, l- (CO-SC2H5 Jetyl, l- (CO-SCH2-C2H5) ethyl,
1- CO-SCH (CH3) 2 Jetyl, 1- (CO-SCH2CH2-C2H5) ethyl, 1- CO-SCH (CH3) -C2H5 J ethyl, 1- [CO-SCH2-CH (CH3) 2] ethyl, 1- CO-SC (CH 3) 3 Jethyl, 2- (CO-SCH 3) ethyl, 2- (CO-SC 2 H 5) ethyl,
2- CO-SCH2-C2H5) ethyl, 2- [CO-SCH (CH3) 2 Jetyl, 2- CO-SCH2CH2-C2H5) ethyl, 2- [CO-SCH (CH3) -C2H5 Jetyl, 2- CO-SCH2 -CH (CH3) 2] ethyl, 2- [CO-SC (CH3) 3 Jetyl, 2- (CO-SCH3J-propyl, 2- (CO-SC2H5) propyl, 2- (CO-SCH2-C2H5 Jpropyl, 2 - CO-SCH (CH3) 2 Jpropyl, 2- (CO-SCH2CH2-C2H5) propyl, 2- CO-SCH (CH3) -C2H5 jpropyl, 2- [C0-SCH2-CH (CH3) 2 Jpropyl, 2- CO -SC (CH3) 3 Jpropyl, 3- (CO-SCH3) propyl, 3- (CO-SC2H5 Jpropyl,
3- CO-SCH2-C2H5 Jpropyl, 3- [CO-SCH (CH3) 2 Jpropyl, 3- CO-SCH2CH2-C2H5) propyl, 3- [CO-SCH (CH3) -C2H5 Jpropyl, 3- CO-SCH2- CH (CH3) 2 Jpropyl, 3- [CO-SC (CH3) 3 J-propyl, 2- C0-SCH3) butyl, 2- (CO-SC2H5) butyl, 2- (CO-SCH2-C2H5) butyl,
2- CO-SCH (CH3) 2 J butyl, 2- (CO-SCH2CH2-C2H5) butyl, 2- CO-SCH (CH3) -C2H5] butyl, 2- [CO-SCH2-CH (CH3) 2 Jbutyl, 2- CO-SC (CH3) 3Jbutyl, 3- (CO-SCH3) butyl, 3- (CO-SC2H5) butyl,
3- CO-SCH2-C2H5) butyl, 3- [CO-SCH (CH3) 2 Jbutyl, 3- CO-SCH2CH2-C2H5) butyl, 3- [CO-SCH (CH3) -C2H5] butyl, CH3) - ut lo, 4- (CO-SC2H5) uo, - - 2- 2 5 uo, 4- [CO-SCH (CH3J2] butyl ?, 4- (CO-SCH2CH2-C2H5) butyl, 4- [CO-SCH (CH3 ) -C2H5Jbutyl, 4- [CO-SCH2-CH (CH3) 2 Jbutyl or 4- [CO-SC (CH3) 3Jbutyl, preferably CH2-CO-SCH3, CH2-CO-SC2H5, 1- (C0-SCH3 Jetyl or 1- (CO-SC2H5) ethyl;
- C6C-alkylsulfinyl: a C? -C -alkylsulfinyl radical, such as, for example, SO-CH3, SO-C2H5, SO-CH2-C2H5, SO-CH (CH3) 2, SO- (n-C4H9) ), SO-CH (CH3) -C2H5, SO-CH-CH (CH3) 2 or SO-C (CH3) 3, or eg SO- (n-C5H ??), 1-methylbutyl-SO, 2-methylbutyl-SO, 3-methylbutyl-SO, 2,2-dimethylpropyl-SO, 1-ethylpropyl-SO, n-hexyl-SO, 1,1-dimethylpropyl-SO, 1,2-dimethylpropyl-SO, 1-methylpentyl-SO, 2-methylpentyl-SO, 3-methylpentyl-SO, 4-methylpentyl-SO, 1,1-dimethylbutyl-SO, 1,2-dimethylbutyl-SO, 1,3-dimethylbutyl- SO, 2,2-dimethylbutyl-SO, 2,3-dimethylbutyl-SO, 3,3-dimethylbutyl-SO, 1-ethyl-butyl-SO, 2-ethylbutyl-SO, 1, 1, 2-trimethylpropyl- SO, 1,2,2-trimethylpropyl-SO, 1-ethyl-1-methylpropyl-SO or 1-ethyl-2-methylpropyl-SO, preferably S0-CH3 / SO-C2H5, SO-CH2-C2H5, SO -CH (CH3), SO- (n-C4H9), SO-C (CH3) 3, SO- (n-C5H ??) or S0- (n-C6H13);
-C 1 -C 4 -Cylsulfinyl-C 1 -C 4 -alkyl: C 1 -C 4 -alkyl substituted by C 1 -C 4 -alkylsulfinyl, such as those mentioned above, namely, eg CH 2 SOCH 3, CH 2 SOC 2 H 5, n-propylsulfinylmethyl, CH 2 SOCH (CH 3) 2, n-butylsulfinylmethyl, (1-methylpropylsulfinyl) methyl, (2-methylpropylsulfinyl) methyl, (1,1-dimethylethylsulfinyl) -methyl, 2-methylsulfinylethyl, 2-ethylsulfinylethyl, 2- (n- propylsulfinyl) ethyl, 2- (1-methylethylsulfinyl) ethyl, 2- (n-butylsulfinyl) ethyl, 2- (1-methylpropylsulfinyl) Jetyl, 2- (2-methylpropylsulfinyl) ethyl, 2- (1, 1-dimethylethylsulfinyl) ethyl, 2- (S0CH3 Jpropyl, 3- (S0CH3) Jpropyl, 2- (SOC2H5) -propyl, 3- (SOC2H5Jpropyl, 3- (propylsulfinyl) propyl, 3- (butylsulfinyl) propyl, 4- (S0CH3) butyl, 4- (SOC2H5) butyl, 4- (n-propylsulfinyl) butyl or 4- (n-butylsulfinyl) butyl, especially für 2- (SOCH3) ethyl;
C 1 -C 4 -haloalkylsulfinyl-C 1 -C -alkyl: C 1 -C 4 -alkyl substituted by C 1 -C 4 -haloalkylsulfinyl, such as those mentioned above, viz. 2- (2, 2, 2- trifluoroethylsulfinyl) -ethyl;
C? -C4-alkylsulfonyl: S02-CH3, S02-C2H5, S02-CH2-C2H5, S02-CH (CH3) 2, n-butylsulfonyl, S02-CH (CH3) -C2H5, S02-CH2-CH (CH3 ) 2 or S02-C (CH3) 3, preferably S02-CH3 or S02-C2H5;
- is preferably substituted by fluoro, chloro, bromo and / or iodo, namely, eg S02-CH2F, S02-CHF2, S02-CF3, S02-CH2C1, S02-CH (C1) 2, S02-C (C1) 3, chlorofluoromethylsulfonyl, dichlorofluoromethylsulfonyl, chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulphonyl, S02-C2F5, 2-fluoropropylsulfonyl, 3- fluoropropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2,3-dichloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3, 3,3-trichloropropylsulfonyl, S02-CH2-C2F5 / S02-CF2-C2F5, 1- (fluoromethyl) -2-fluoroethylsulfonyl, 1- (chloromethyl) -2-chloroethylsulfonyl, 1- (bromomethyl) -2- bromoethylsulfonyl, 4-fluoro butylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl, preferably S02-CH2C1, S02-CF3 or 2,2,2-trifluoroethylsulfonyl;
- Cx-Cd-alkylsulfonyl: a C? -C4-alkylsulfonyl radical such as those mentioned above, or for example S02- (n-CsH ??), l-methylbutyl-S02, 2-methylbutyl-S02, 3-methylbutyl -S02, 2,2-dimethylpropyl-S02, l-ethylpropyl-S02, n-hexyl-S02, 1, l-dimethylpropyl-S02, 1,2-dimethylpropyl-S0, l-methylpentyl-S02, 2-methylpentyl -S02, 3-methyl-pentyl-S02, 4-methylpentyl-S02, 1, l-dimethylbutyl-S02, 1,2-dimethylbutyl-S02 / l, 3-dimethylbutyl-S02, 2, 2-dimethylbutyl-S02 , 2,3-dimethylbutyl-S02, 3,3-dimethylbutyl-S02, l-ethylbutyl-S02, 2-ethylbutyl-S02, 1, 1, 2-trimethylpropyl-S02, 1,2,2-trimethylpropyl-S02 , l-ethyl-l-methylpropyl-S02 or l-ethyl-2-methylpropyl-S02, preferably S02-CH3, S02-C2H5, S02-CH2-C2H5, S02-CH (CH3) 2, S02- (n-C4H9 ), S02-C (CH3) 3, S02- (n-C5H ??) or S02- (n-C6H? 3);
- C 1 -C 4 -alkylsulfonyl-C?-C 4 -alkyl: C?-C 4 -alkyl substituted by C?-C 4 -alkylsulfonyl as mentioned above, namely, eg CH 2 S0 2 -CH 3, CH 2 S0 2 -C 2 H 5, CH 2 S0 2 -CH2-C2H5, CH2S02-CH (CH3) 2, CH2S0 -CH2CH2-C H5, (l-methylpropylsulfonyl) methyl, (2-methylpropylsulfonylmethyl, CH2S02-C (CH3) 3, CH (CH3) S02-CH3, CH (CH3) S02-C2H5, CH2CH2S02-CH3, CH2CH2S02-C2H5, CH2CH2S02-CH2-C2H5, CH2CH2S02-CH (CH3) 2, CH2CH2S02-CH2CH2-C2H5, 2- (1-methylpropyl-sulphonyl) ethyl, 2- ( 2-Methylpropylsulfonyl) ethyl, CH2CH2S02-C (CH3) 3, 2- (S02-CH3) Jpropyl, 2- (S02-C2H5) J-propyl, 2- (S02-CH2-C2H5-J-propyl, 2- [S02-CH (CH3) 2 -propyl , 2- (S02-CH2CH2-C2H5) J-propyl, 2- (l-methyl-propylsulfonyl-J-propyl, 2- (2-methyl-propylsulfonyl-J-propyl, 2- [S02-C (CH3) 3-Jpropyl, 3- (S02-CH3-Jpropyl, 3- (S02-C2H5) propyl, - 2- H2 H2- 2 5 prop or, - -me prop prop prop,
3- (2-Methylpropylsulfonyl) ropyl, 3- [S02-C (CH3) 3 J-propyl, 2- (S02-CH3 Jbutyl, 2- (S02-C2H5) butyl, 2- (S02-CH2-C2H5) butyl,
2- [S0 -CH (CH3) 2 Jbutyl, 2- (S02-CH2CH2-C2H5) butyl, 2- (1-methylpropylsulfonyl) butyl, 2- (2-methylpropylsulfonyl) butyl, 2- [S02-C ( CH3) 3-Butyl, 3- (S02-CH3 Jbutyl, 3- (S02-C2H5 Jbutyl,
3- (S ?2-CH2-C2H5) butyl, 3- [S02-CH (CH3) 2] butyl, 3- (S02-CH2CH2-C2H5) butyl, 3- (1-methylpropylsulfonyl) butyl,
3- (2-Methylpropylsulfonyl) butyl, 3- [S02-C (CH) 3 Jbutyl, 4- (S02-CH3 Jbutyl, 4- (S02-C2H5) butyl, 4- (S? 2-CH2-C2H5) butyl,
4- [S02-CH (CH3) 21butyl, 4- (S02-CH2CH2-C2H5) butyl, 4- (1-methylpropylsulfonylbutyl, 4- (2-methylpropylsulfonyl) butyl or 4- [S02-C (CH3) 3 Jbutyl , especially CH2CH2S02-CH3 or CH2CH2S02-C2H5;
C? -C4-halogenoalkylsulfonyl-C? -C4-alkyl: C? -C4-alkyl substituted by C? -C4-halogenoalkylsulfonyl as mentioned above, ie, p. 2- (2, 2, 2-trifluoroethylsulphonyl-ethyl;
C? -C4-alkylamino-C? -C4-alkyl: C? -C4-alkyl substituted by C? -C4-alkylamino, such as, for example, H3C-NH-, H5C-H-, n-propyl-NH- , 1-methylethyl-NH-, n-butyl-NH-, 1-methylpropyl-NH-, 2-methylpropyl-NH- and 1,1-dimethylethyl-NH-, preferably H3C-NH- or H5C2-NH-, a know, for example, CH2CH2-NH-CH3, CH2CH2-N (CH3) 2, CH2CH2-NH-C2H5 or CH2CH2- (C2H5) 2;
- (C -C4-alkylamino) carbonyl: C0-NH-CH3, C0-NH-C2H5, n-propylamino, C0-NH-CH (CH3) 2, C0-NH-CH2CH2-C2H5, C0-NH- CH (CH3) -C2H5, C0-NH-CH2-CH (CH3) 2 or C0-NH-C (CH3) 3, preferably C0-NH-CH3 or C0-NH-C2H5;
- (C? -C6-alkylamino) carbonyl: one of the abovementioned (C? -C4-alkylamino) carbonyl radicals, or for example CO-NH- (n-C5H ??), l-methylbutyl- NHCO-, 2-methylbutyl-NHCO-, 3-methylbutyl-NHCO-, 2,2-dimethylpropyl-NHCO-, 1-ethylpropyl-NHCO-, CO-NH- (n-C6H13), 1,1-dimethylpropyl-NHCO -, 1, 2-dimethylpropyl-NHCO-, 1-methyl pentyl-NHCO-, 2-methylpentyl-NHCO-, 3-methylpentyl-NHCO-, 4-methyl-pentyl-NHCO-, 1,1-dime-ilbutyl- NHCO-, 1,2-dimethylbutyl-NHCO-, 1,3-dimethylbutyl-NHCO-, 2,2-dimethylbutyl-NHCC-, 2,3-dimethylbutyl-NHCO-, 3,3-dimethylbutyl-NHCO-, 1-ethylbutyl-NHCO-, 2-ethylbutyl-NHCO-, 1,1,2-trimethylpropyl-NHCO-, 1, 2, 2-trimethylpropyl-NHCO-, 1-ethyl-1-methylpropyl-NHCO- or -ethyl-2-methylpropyl-NHCO-, preferably C0-NH-CH3, CO-NH-C2H5, CO-NH-CH2-C2H5, CO-NH- - n- 6? 3;
- (C? -C4-alkylamino) carbonyl-C? -C4-alkyl: (C? -C4-alkylamino) carbonyl as those mentioned above, preferably CO-NH-CH3 or CO-NH-C2H5, substituents C? -C4-alkyl, eg CH2-CO-NH-CH3, CH2-CO-NH-C2H5, CH2-CO-NH-CH2-C2H5, CH2-CO-NH-CH (CH3) 2, CH2-CO -NH-CH2CH2-C2H5, CH2-CO-NH-CH (CH3) -C2H5, CH2-CO-NH-CH2-CH (CH3) 2, CH2-CO-NH-C (CH3) 3, CH (CH3) -CO-NH-CH3, CH (CH3) -CO-NH-C2H5, 2- (CO-NH-CH3) ethyl, 2- (CO-NH-C2H5) ethyl, 2- (CO-NH-CH2-C2H5 ) - ethyl, 2- [CH2-CO-NH-CH (CH3) 2] ethyl, 2- (CO-NH-CH2CH2-C2H5) ethyl, 2- [CO-NH-CH (CH3) -C2H5-Jetyl, 2 - [CO-NH-CH2-CH (CH3) 2 Jetyl, 2- [CO-NH-C (CH3) 3 Jetyl, 2- (CO-NH-CH3) propyl, 2- (CO-NH-C2H5) pro - pyl, 2- (CO-NH-CH2-C2H5) J-propyl, 2- [CH2-CO-NH-CH (CH3) 2 J-propyl, 2- (CO-NH-CH2CH2-C2H5) propyl,
2- [CO-NH-CH (CH 3) -C 2 H 5] propyl, 2- [CO-NH-CH 2 -CH (CH 3) 2 J-propyl, 2- [CO-NH-C (CH 3) 3 J-propyl, 3- (CO -NH-CH3 Jpropyl, 3- (CO-NH-C2H5) propyl, 3- (CO-NH-CH2-C2H5) propyl, 3- [CH2-C0-NH-CH (CH3) 2] propyl ?, 3- (C0-NH-CH2CH2-C2H5) propyl, 3- [CO-NH-CH (CH3) -C2H5Jpropyl, 3- [CO-NH-CH2-CH (CH3) 2 J-propyl, 3- [CO-NH-C ( CH3) 3 J-propyl, 2- (C0-NH-CH3 Jbutyl, 2- (C0-NH-C2H5) -butyl, 2- (CO-NH-CH2-C2H5) butyl, 2- [CH2-C0-NH-CH (CH3) 2] butyl, 2- (CO-NH-CH2CH2-C2H5) butyl, 2- [CO-NH-CH (CH3) -C2H5] butyl, 2- [CO-NH-CH2-CH (CH3) 2 Jbutyl, 2- [CO-NH-C (CH3) 3 Jbutyl, 3- (CO-NH-CH3) butyl, 3- (CO-NH-C H5 Jbutyl, 3- (CO-NH-CH2-C2H5) - butyl,
3- [CH2-CO-NH-CH (CH3) 2 Jbutyl, 3- (CO-NH-CH2CH2-C2H5) butyl, 3- [CO-NH-CH (CH3) -C2H5 Jbutyl, 3- [CO-NH -CH2-CH (CH3) 2 Jbutyl,
3- [CO-NH-C (CH3) 3 Jbutyl, 4- (CO-NH-CH3 Jbutyl, 4- (CO-NH-C2H5) butyl, 4- (CO-NH-CH2-C2H5 Jbutyl, 4 - [CH -CO-NH-CH (CH3) 2 Jbutyl,
4- (CO-NH-CH2CH2-C2H5) butyl, 4- [CO-NH-CH (CH3) -C2H5 Jbutyl, 4- [CO-NH-CH2-CH (CH3) 2 Jbutyl or 4- [CO-NH -C (CH3) 3 -butyl, preferably CH2-C0-NH-CH3, CH2-C0-NH-C2H5 CH (CH3) -C0-NH-CH3. or CH (CH3) -CO-NH-C2H5.
- di (C? -C4-alkyl) amino: N (CH3) 2, N (C2H5) 2, N, N-dipropylamino, N, N-di- (1-methylethyl) amino, N, N-dibutylamino, N , N-di- (l-methylpropyl) amino, N, N-di- (2-methylpropyl) amino, N, N-di- (1,1-dimethylethyl) amino, N-ethyl-N-methylamino, N- methyl-N-propylamino, N-methyl-N- (1-methylethyl) amino, N-butyl-N-methylamino, N-methyl-N- (1-methylpropyl) amino, N-methyl-N- (2 -methylpropyl) amino, N- (1,1-dimethylethyl) -N-methylamino, N-ethyl-N-propylamino, N-ethyl- N- (1-methylethyl) amino, N-butyl-N-ethylamino, N- ethyl-N- (1-methyl-propyl) amino, N-ethyl-N- (2-methylpropyl) amino, N-ethyl-N- (1,1-dimethylethyl) amino, N- (1-methylethyl) -N-propylamino, N-butyl-N-propylamino, N- (1-methylpropyl) -N-propylamino, N- (2-methylpropyl) -N- propylamino, N- (1,1-dimethylethyl) -N -propylamino, N-butyl- - -me and - - -, -, - tyl) -N- (1-methylethyl) amino, N-butyl-N- (1-methylpropyl) amino, N-butyl-N- ( 2-methylpropyl) amino, N-butyl-N- (1,1-dimethylethyl) -amino, N- (1-methylpropyl) -N- (2-methylpropyl) amino, N- (1,1-dimethyl) tl) -N- (1-methylpropyl) amino or N- (1,1-dimethylethyl) -N- (2-methylpropyl) amino, preferably N (CH 3) 2 or N (C 2 H 5) 2;
di (C? -C4-alkyl) amino-C? -C4-alkyl: C? -C4-alkyl substituted by di (C? -C4-alkyl) -amino as mentioned above, namely, eg CH2N (CH 3) 2, CH 2 N (C 2 H 5) 2, N, N-dipropylaminomethyl, N, N-di [CH (CH 3) 2 J aminomethyl, N, N-dibutylaminomethyl, N, N-di- (1-methylpropyl) aminomethyl, N, -di (2-methylpropyl) aminomethyl, N, N-di [C (CH3) 3 Jaminomethyl, N-ethyl-N-methylaminomethyl, N-methyl-N-propylaminomethyl, N-methyl-N- [CH (CH3 ) 2 Jaminomethyl, N-butyl-N-methylaminomethyl, N-methyl-N- (1-methylpropylJaminomethyl, N-methyl-N- (2-methylpropyl) aminomethyl, N- [C (CH3) J-N-methylaminomethyl, N -ethyl-N-propylaminomethyl, N-ethyl-N- [CH (CH3) 2 Jaminome-tyl, N-butyl-N-ethylaminomethyl, N-ethyl-N- (1-methylpropyl Jaminomethyl, N-ethyl-N- ( 2-methylpropyl) aminomethyl, N-ethyl-N- [C (CH 3) 3 Jaminomethyl, N- [CH (CH 3) 2 JN-propylaminomethyl, N-buyl-N-propylaminomethyl, N- (1-methylpropyl) - N-propylaminomethyl, N- (2-methylpropyl) -N-propylaminomethyl, N- [C (CH3) 3] -N-propylammiomethyl, N-butyl-N- (1-methylethyl) -aminome linden, N- [CH (CH3) 21-N- (1-methylpropyl) aminomethyl, N- [CH (CH3) 2] -N- (2-methylpropylJaminomethyl, N- [C (CH3) 3] -N- [ CH (CH 3) 2 Jaminomethyl, N-butyl-N- (1-methylpropyl) aminomethyl, N-butyl-N- (2-methylpropyl) aminomethyl, N-butyl-N- [C (CH 3) 3 J -aminomethyl, N - (1-methyl-propyl) -N- (2-methylpropyl) aminomethyl, N- [C (CH 3) 3] -N- (1-methylpropyl) aminomethyl, N- [C (CH 3) 3 J -N- ( 2-methylpropyl) aminomethyl, N, N-dimethylaminoethyl, N, N-diethylaminoethyl, N, N-di (n-pro-p-phenylamino, N, N-di- [CH (CH 3) 2] -aminoethyl, N, N- dibutylami-noethyl, N, -di (1-methylpropylCheminoethyl, N, N-di (2-methylpropapyaminoethyl, N, N-di- [C (CH3) 3 J-aminoethyl, N-ethyl-N-methylamino- noethyl, N-methyl-N-propylaminoethyl, N-methyl-N- [CH (CH3) 2 Jaminoethyl, N-butyl-N-methylaminoethyl, N-methyl-N- (1-methylpro-pyl) aminoethyl, N-methyl -N- (2-methylpropyl) aminoethyl, - [C (CH3) 3 JN-methylaminoethyl, N-ethyl-N-propylaminoethyl, N-ethyl-N- [CH (CH3) 2 Jaminoethyl, N-butyl-N-ethylaminoethyl , N-ethyl-N- (1-methylpropyl) aminoethyl, N-et il-N- (2-methylpropyl) aminoethyl, N-ethyl-N- [C (CH 3) 3 J aminoethyl, N- [CH (CH 3) 2 J-N-propylamino-tyl, N-butyl-N-propylaminoethyl, N- (1-methylpropyl) -N-propylaminoethyl, N- (2-methylpropyl) -N-propylaminoethyl, N- [C (CH 3) 3 JN-propylaminoethyl, N-butyl-N- [CH (CH 3) 2 Jaminoethyl, N- [CH (CH3) 2] -N- (1-methylpropyl) aminoethyl, N- [CH (CH3) 2] -N- (2-methylpropyl) -aminoethyl, N- [C (CH3) 3J- N- [CH (CH3) 2 Jaminoethyl, N-bu- neo, - - - 3 3, - -me - - (2-methylpropyl) aminoethyl, N- [C (CH3) 3 J -N- (1-methylpropyl ) - aminoethyl or N- [C (CH3) 3 JN- (2-methylpropylChaminoethyl, especially fN, N-dimethylaminoethyl or N, N-diethylaminoethyl;
- di (C -C4-alkyl) aminocarbonyl: CO-N (CH3) 2, CO-N (C2H5), CO-N (CH2-C H5) 2, CO-N [CH (CH3) 2J2, N, N -dibutylaminocarbonyl,
CO-N [CH (CH3) -C2H5] 2, CO-N [CH2-CH (CH3) 2J2, C0-N [C (CH3) 3J2, N-ethyl-N-methylaminocarbonyl, N-methyl-N -propylaminocarbonyl, N-methyl-N- [CH (CH3) 2] aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N- (1-methylpropyl) aminocarbonyl, N-methyl-N- (2- methylpropyl) aminocarbonyl, N- [C (CH 3) 3] -N-methylaminocarbonyl, N-ethyl-N-propylaminocarbonyl, N-ethyl-N- [CH (CH 3) 2 J -aminocarbonyl, N-butyl-N- ethylaminocarbonyl, N-ethyl-N- (1-methylpropap) aminocarbonyl, N-ethyl-N- (2-methylpropyl) aminocarbonyl, N-ethyl-N- [C (CH 3) 3 J aminocarbonyl, N- [CH ( CH3) 2 J-N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl, N- (1-methylpropyl) -N-propylaminocarbonyl, N- (2-methylpropyl) -N-propylaminocarbonyl, N- [C (CH3) 3 J-N-propylaminocarbonyl, N-butyl-N- [CH (CH 3) 2 J aminocarbonyl, N- [CH (CH 3) 2] -N- (1-methylpropyl) aminocarbonyl, N- [CH (CH 3) 2] -N- (2-methylpropyl) aminocarbonyl, N- [C (CH3) 3 J -N- [CH (CH3) 2J aminocarbonyl, N-butyl- N- (1-methylpropyl) aminocarbonyl , N-butyl-N- (2-methylpropyl) -aminocarbonyl, N-butyl-N- [C (CH3) J aminocarbonyl, N- (l-methyl-propyl) -N- (2-methylpropyl) aminocarbonyl, N- [C (CH3) 3 J-N- (1-methylpropyl) ammonocarbonyl or N- [C (CH3) 3] -N- (2-methylpropyl) aminocarbonyl, preferably CO-N (CH3) 2 or CO-N (C2H5 );
- di (C? -C6-alkyl) aminocarbonyl: one of the di (C? -C4-alkyl) aminocarbonyl radicals mentioned above, or for example N (CH3) - (n-C5H ??), N (C2H5) ) - (n-C5H ??), N (CH2-C2H5) - (n-C5H ??), N (n-C4H9) - (n-C5H ??), N (n-C5Hu) - (n- C5H ??), N (n-C6H? 3) - | n-C5Hn), N (CH3) - (n-C6H? 3), N (C2H5) - (n-C6H? 3), N (CH2-) C2H5) - (n-C6H? 3), N (n-C4H9) - (n-C6H13), N (n-C5H ??) - (n-C6H? 3) or N (n-C6H13) 2;
di (C-C4-alkyl) aminocarbonyl-C? -C4-alkyl: C? -C4-alkyl substituted by di (C? -C4-alkyl) aminocarbonyl as mentioned above, preferably CO-N (CH3) 2 or CO -N (C2H5), namely, eg CH2-CO-N (CH3) 2, CH2-CO-N (C2H5) 2, CH (CH3) -C0-N (CH3) 2 or CH (CH3) -CO-N (C2H5) 2, preferably CH2-CO-N (CH3) 2 or CH (CH3) -CO-N (CH3J2;
- di (C? -C4-alkyl) -phosphonyl-C? -C4-alkyl: C? -C-alkyl substituted by di (C? -C-alkyl) -phosphonyl, such as, for example -PO (OCH3) 2, -PO (OC2H5) 2, N, N-dipropylphosphonyl, N, N-di- (1-methylethyl) phosphonyl, N, N-dibutylphosphonyl, N, N-di- (1-methylpropyl) phosphonyl, nyl, N-ethyl -N-methylphosphonyl, N-methyl-N-propylphosphonyl, N-methyl-N-1-methylethyl) phosphonyl, N-butyl-N-methylphosphonyl, N-methyl-N- (1-methylpropyl) -phosphonyl, N-methyl- N- (2-methylpropyl) phosphonyl, N- (1, 1-dimethylethyl) -N-methylphosphonyl, N-ethyl-N-propyl-phosphonyl, N-ethyl-N- (1-methylethyl) phosphonyl, N- butyl-N-ethylphos-fonyl, N-ethyl-N- (1-methylpropyl) phosphonyl, N-ethyl-N- (2-methyl-propyl) phosphonyl, N-ethyl-N- (1,1-dimethylethyl) phosphonyl) , N- (1-methylethyl) -N-propylphosphonyl, N-butyl-N-propylphosphonyl, N- (1-methylpropyl) -N-propylphosphonyl, N- (2-methylpropyl) -N-propylphospho-nyl, N - (1, 1-dimethylethyl) -N-propylphosphonyl, N-butyl-N- (1-methylethyl) phosphonyl, N- (1-methylethyl) -N- (1-methylpropyl) phosphonyl, N- (1- methylethyl) -N- (2-methylpropyl) fo Sphonyl, N- (1,1-dimethylethyl) -N- (1-methylethyl) phosphonyl, N-butyl-N- (1-methylpropyl) phospho-nyl, N-butyl-N- (2-methylpropyl) phosphonyl, N -butyl-N- (1, 1-dimethylethyl) phosphonyl, N- (1-methylpropyl) -N- (2-methylpropyl) -phosphonyl, N- (1, 1-dimethylethyl) -N- (1-methylpropyl) phosphonyl) or N- (1,1-dimethylethyl) -N- (2-methylpropyl) phosphonyl, preferably -PO (OCH3) 2 or -PO (OC2H5) 2, namely, eg CH2-P0 (0CH3) 2, CH2-PO (OC2H5) 2, CH (CH3) -PO (OCH3) 2 or CH (CH3) -PO (OC2H5) 2;
C -C6-alkenyl: prop-1-en-l-yl, allyl, 1-methyletenyl, 1-bu-ten-1-yl, l-buten-2-yl, l-buten-3-yl, 2- buten-1-yl, 1-methyl-prop-1-en-1-yl, 2-methyl-prop-1-en-1-yl, 1-methyl-prop-2-en-1-yl, 2-methyl-prop-2-en-l-yl, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1-methyl- but-1-en-l-yl, 2-methyl-but-l-en-l-yl, 3-methyl-but-l-en-l-yl, l-methyl-but-2-en-l- ilo, 2-methyl-but-2-en-l-yl, 3-methyl-but-2-en-l-yl, l-methyl-but-3-en-l-yl, 2-methyl-but- 3-en-l-yl, 3-methyl-but-3-en-l-yl, 1, l-dimethyl-prop-2-en-l-yl, 1,2-dime-yl-prop-1- en-l-yl, 1,2-dimet-il-prop-2-en-1-yl, 1-ethyl-prop-l-en-2-yl, l-ethyl-prop-2-en-l-yl , n-hex-1-en-l-yl, n-hex-2-en-l-yl, n-hex-3-en-l-yl, n-hex-4-en-l-yl, n -hex-5-en-l-yl, 1-methyl-pent-l-en-l-yl, 2-methyl-pent-1-en-l-yl, 3-methyl-pent-l-en-l -yl, 4-methyl-pent-1-en-l-yl, l-methyl-pent-2-en-l-yl, 2-methyl-pent-2-en-l-yl, 3-methyl-pent -2-en-l-yl, 4-methyl-pent-2-en-l-yl, l-methyl-pent-3-en-l-yl, 2-methyl-pent-3-en-l-yl 3-methyl-pent-3 -in-l-yl, 4-methyl-pent-3-en-l-yl, l-methyl-pent-4-en-l-yl, 2-methyl-pent-4-en-l-yl, 3 -methyl-pent-4-en-l-yl, 4-methyl-pent-4-en-l-yl, 1, l-dimethyl-but-2-en-l-yl, 1,1-dimethyl-but -3-en-l-yl, 1, 2-dimethyl-but-l-en-l-yl, 1,2-dimethyl-but-2-en-l-yl, 1,2-dimethyl-but-3 -in-l-yl, 1,3-dimethyl-but-1-en-l-yl, l, 3-dimethyl-but-2-en-l-yl, 1,3-dimethyl-but-3-en -l-ilo, 2, 2-dimethyl-but-3-en-l-yl, 2,3-dimethyl-but-1-en-l-yl, 2,3-dimethyl-but-2-en-l -yl, 2, 3-dimethyl-ut-2-en-l-yl, 1-et l-but- -en- - o, -e-u - -en- - o, l-ethyl-but-3 -in-l-yl, 2-ethyl-but-l-en-l-yl, 2-ethyl-but-2-en-l-yl, 2-ethyl-but-3-en-l-yl, 1 , 1,2-trimethyl-prop-2-en-l-yl, l-ethyl-l-methyl-prop-2-en-l-yl, l-ethyl-2-methyl-prop-1-en -l-ilo or l-ethyl-2-methyl-prop-2-en-l-yl;
C3-Cg-halogenoalkenyl: C3-Cg-alkenyl as mentioned above, which is partially or completely substituted by fluoro, chloro, bromo and / or iodo, namely, eg 2-chloroalyl, 3-chloroalyl, 2,3-dichloroallyl, 3, 3-dichloroallyl, 2,3, 3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromoalyl, 3-bromoalyl, 2,3-dibromoallyl, 3, 3- dibromoalyl, 2,3,3-tribromoalyl or 2,3-dibromo-but-2-enyl;
cyano-C -C6-alkenyl: eg 2-cyanoalyl, 3-cyanoalyl, 4-cyanobut-2-enyl, 4-cyanobut-3-enyl or 5-cyanopent-4-enyl;
- C3-C6-alkynyl: prop-1-yn-l-yl, prop-2-yn-l-yl, n-but-1-yn-l-yl, n-but-l-yn-3-yl , n-but-l-in-4-yl, n-but-2-yn-l-yl, n-pent-1-yn-l-yl, n-pent-l-in-3-yl, n - pent-l-in-4-yl, n-pent-l-in-5-yl, n-pent-2-yn-l-yl, n-pent-2-yn-4-yl, n-pent -2-in-5-yl, 3-methyl-but-l-in-3-yl, 3-methyl-but-l-in-4-yl, n-hex-1-yn-l-yl, n -hex-l-in-3-yl, n-hex-l-in-4-yl, n-hex-l-in-5-yl, n-hex-l-in-6-yl, n-hex -2-in-l-yl, n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3 -in-l-yl, n-hex-3-yn-2-yl, 3-methyl-pent-l-yn-l-yl, 3-methyl-pent-l-yn-3-yl, 3-methyl - pent-l-in-4-yl, 3-methyl-pent-l-in-5-yl, 4-methyl-pent-1-yn-l-yl, 4-methyl-pent-2-in-4 -yl and 4-methyl-pent-2-yn-5-yl, preferably prop-2-yn-l-yl;
- C3-C6-haloalkylquinyl: C3-C6-alkynyl as mentioned above, which is partially or completely substituted by fluoro, chloro, bromo and / or iodo, namely, eg 1,1-difluoroprop-2 -in-l-yl, 4-fluorobut-2-yn-l-yl, 4-chlorobut-2-yn-l-yl, 1,1-difluorobut-2-yn-l-yl, 5-fluoropent-3 -in-l-yl or 6-fluoro-hex-4-yn-l-yl;
- cyano-C3-C6-alkynyl: eg 3-cyanopropargyl, 4-cyanobut-2-yn-l-yl, 5-cyanopent-3-yn-l-yl and 6-cyanohex-4-yl -ilo;
- C3-C4-alkenyloxy-C? -C4-alkyl: C-C4-alkyl substituted by C3-C4-alkenyloxy, such as, for example, allyloxy, but-l-en-3-yloxy, but-l-en- 4-yloxy, but-2-en-l-yloxy, l-methylprop-2-enyloxy or 2-methylprop-2-enyloxy substituents, viz., For example, pertain to 2-allyloxy ethers;
C3-C4-alkynyloxy-C? -C -alkyl: C? -C -alkyl substituted by c3_c4-alkynyloxy, such as, for example, propargyloxy, but-l-in-3-yloxy, but-l-in-4- iloxy, but-2-in-l-yloxy, l-methylprop-2-ynyloxy or 2-methylprop-2-ynyloxy, preferably propargyloxy, viz., for example, propargyloxymethyl or 2-propargyloxyethyl, especially 2-propargyloxyethyl;
C3-C4-alkenylthio-C? -C4-alkyl: C? -C4-alkyl substituted by C3-C-alkenylthio, such as, for example, allylthio, but-l-en-3-ylthio, but-l-en- 4-ylthio, but-2-en-l-ylthio, l-methylprop-2-enylthio or 2-methylprop-2-enylthio, viz., For example, allylthiomethyl, 2-allylthioethyl or but-l-en-4- Ithiomethyl, especially für 2- (allylthio) ethyl;
- < _3-C4-alkynylthio-C? -C4-alkyl: C? -C4-alkyl substituted by C3-C4-alkynylthio, such as, for example, propargylthio, but-l-in-3-ylthio, but-l-in 4-ilthio, but-2-in-l-ilthio, l-methylprop-2-inylthio or
2-methylprop-2-inylthio, preferably propargylthio, viz., For example, propargylthiomethyl or 2-propargthylthioethyl, especially 2- (propargthylthio) -ethyl;
- C3-C-alkenylsulfinyl-C? -C4-alkyl: C? -C4-alkyl substituted by C3-C4-alkenylsulfinyl, such as, for example, allylsulfinyl, but-l-en-3-ylsulfinyl, but-l-en 4-ylsulfinyl, but-2-en-l-yl-sulfinyl, l-methylprop-2-enylsulfinyl or 2-methylprop-2-enylsulfinyl, viz., For example, allylsulfinylmethyl, 2-allylsulphylethyl or -l-en-4-ylsulfinylmethyl, especially für 2- (allylsulfinyl) ethyl;
- C3-C4-alkynylsulfinyl-C? -C4-alkyl: C? -C -alkyl substituted by C3-C4-alkynylsulfinyl, such as, for example, propargyl-sulfinyl, but-l-in-3-ylsulfinyl, but-l-in 4-ylsulfinyl, but-2-yn-l-yl-sulfinyl, l-methylprop-2-ynylsulfinyl or 2-methylprop-2-ynylsulfinyl, preferably propargyl-sulfinyl, viz., For example, propargyl-sulfinylmethyl or 2-propargyl-sulfinylethyl, especially 2- (propargyl-sulfinyl) ethyl;
C3-C4-alkenylsulfonyl-C? -C4-alkyl: C? -C4-alkyl substituted by C3-C4-alkenylsulfonyl, such as, for example, allylsulfonyl, but-l-en-3-ylsulfonyl, but-l-en- 4-ylsulfonyl, but-2-en-l-yl-sulfonyl, l-methylprop-2-enylsulfonyl or 2-methylprop-2-enylsulphonyl, viz., For example, allylsulfonylmethyl, 2-allylsulfo-sulfonyl) ethyl;
C3-C4-alkynylsulfonyl-C? -C4-alkyl: C? -C4-alkyl substituted by C3-C-alkynylsulfonyl, such as, for example, propargyl-sulfonyl, but-l-in-3-ylsulfonyl, but-l-in 4-ylsulfonyl, but-2-yn-l-yl-sulfonyl, l-methylprop-2-ynylsulfonyl or 2-methylprop-2-ynylsulphonyl, preferably propargyl-sulfonyl, viz., For example, propargylsulphonylmethyl or 2-propargyl-sulfonylethyl, especially , 2- (propargylsulfonyl) ethyl;
- C3-Cg-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
- C3-C8-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl;
- C3-C8-cycloalkyl-C? -Cg-alkyl: eg cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cycloheptylmethyl, cyclooctylmethyl, 2- (cyclopropyl) ethyl, 2- (cyclobutyljethyl, 2- (Cyclopentyl, Jetyl, 2- (cyclohexyl) ethyl, 2- (cycloheptyl, Jetyl, 2- (cyclooctyl) ethyl, 3- (cyclopropyl, Jpropyl, 3- (cyclobutyl) propyl, 3- (cyclopentyl) propyl, 3- (cyclohexyl-propyl, 3- (cycloheptyl) propyl, 3- (cyclooctyl) propyl, 4- (cyclopropyl-Jbutyl, 4- (cyclobutyl) butyl, 4- (cyclopentyl-Jbutyl, 4- (cyclohexyl) -butyl, 4- ( cycloheptylbutyl, 4- (cycloocrylbutyl, 5- (cyclopropyl) pentyl, 5- (cyclobutyl) pentyl, 5- (cyclopentyl) -pentyl, 5- (cyclohexyl) pentyl, 5- (cycloheptyl) pentyl, 5- ( cyclooctyl) pentyl, 6- (cyclopropyl) hexyl, 6- (cyclobutyl) hexyl, 6- (cyclopentyl) hexyl, 6- (cyclohexyl) hexyl, 6- (cycloheptyl) hexyl or 6- (cyclooctyl) hexyl;
- C3-C8-cycloalkyloxy-C? -C4-alkyl: cyclopropyloxymethyl, 1-cyclopropyloxy-ethyl, 2-cyclopropyloxy-ethyl, 1-cyclopropyloxy-prop-1-yl, 2-cyclopropyloxy-prop-1-yl, 3-cyclopropyloxy-prop-1-yl, 1-cyclopropyloxy-but-1-yl, 2-cyclopropyloxy-butyl-1-yl, 3-cyclopropyloxy-but-1-yl, 4-cyclopropyloxy-butyl-1-yl, l-cyclopropyloxy-but-2-yl, 2-cyclopropyloxy-but-2-yl, 3-cyclopropyloxy-but-2-yl, 3-cyclopropyloxy-but-2-yl, 4-cyclopropyloxy-but-2-yl, 1- (cyclopropyloxymethyl) -et-1-yl, 1- (cyclopropyloxymethyl) -l- (CH 3) -et-1-yl, 1- (cyclopropylmethyloxy) -prop-1-yl, cyclobutyloxymethyl, 1- cyclobutyloxy-ethyl, 2-cyclobutyloxy-ethyl, 1-cyclobutyloxy-prop-1-yl, 2-cyclobutyloxy-prop-1-yl, 3-cyclobutyloxy-1-yl, 1-cyclobutyloxy-but-l- ilo, 2-cyclobutyloxy-but-1-yl, 3-cyclobutyloxy-but-1-yl, 4-cyclobutyloxy-but-1-yl, 1-cyclobutyloxy-but-2-yl, 2-cyclobutyloxy-1-yl , 4-c-clobut-ox-ut- - or, -ccou oxethyl) et-l-yl, 1- (cyclobutyloxymethyl) -l- (CH 3) -et-1-yl, 1- (cyclob) utiloxymethyl) prop-l-yl, cyclopentyloxymethyl, 1-cyclopentyloxy-ethyl, 2-cyclopentyloxy-ethyl, 1-cyclopentyloxy-prop-1-yl, 2-cyclopentyloxy-propyl-1-yl, 3-cyclopentyloxy-propyl 1-yl, 1-cyclopentyloxy-but-1-yl, 2-cyclopentyloxy-but-1-yl, 3-cyclopentyloxy-but-1-yl, 4-cyclopentyloxy-butyl-1-yl, l-cyclopentyloxy-butyl 2-yl, 2-cyclopentyloxy-but-2-yl, 3-cyclopentyloxy-but-2-yl, 3-cyclopentyloxy-but-2-yl, 4-cyclopentyloxy-but-2-yl, l- (cyclopentyloxymethyl) ) et-l-yl, l- (cyclopentyloxymethyl) -l- (CH3J- et-l-yl, l- (cyclopentyloxymethyl) prop-l-yl, cyclohexyloxymethyl, 1-cyclohexyloxy-ethyl, 2-cyclohexyloxy-ethyl , 1-cyclohexyloxy-prop-1-yl, 2-cyclohexyloxy-prop-1-yl, 3-cyclohexyloxy-1-yl, 1-cyclohexyloxy-but-1-yl, 2-cyclohexyloxy-but-1 -yl, 3-cyclohexyloxy-but-l-yl, 4-cyclohexyloxy-but-1-yl, l-cyclohexyloxy-but-2-yl, 2-cyclohexyloxy-but-2-yl, 3-cyclohexyloxy-but-2 -yl, 3-cyclohexyloxy-but-2-yl, 4-cyclohexyloxy-but-2-yl, l- (cyclohexyloxymethyl) et-1-yl, l- (cyclo) hexhexyloxymethyl) -l- (CH 3) -et-l-yl, 1- (cyclohexyloxymethyl) -prop-1-yl, cycloheptyloxymethyl, 1-cycloheptyloxy-ethyl, 2-cycloheptyloxy-ethyl, 1-cycloheptyloxy-prop -1-yl, 2-cycloheptyloxy-prop-1-yl, 3-cycloheptyloxy-1-yl, 1-cycloheptyloxy-but-1-yl, 2-cycloheptyloxy-but-1-yl, 3-cycloheptyloxy-but -l-ilo, 4-cycloheptyloxy-but-1-yl, l-cycloheptyloxy-but-2-yl, 2-cycloheptyloxy-but-2-yl, 3-cycloheptyloxy-but-2-yl, 3-cycloheptyloxy-but -2-yl, 4-cycloheptyloxy-but-2-yl, 1- (cycloheptyloxymethyl) et-1-yl, 1- (cycloheptyloxymethyl) -l- (CH 3) -et-1-yl, 1- (cycloheptyloxymethyl) prop-l-yl, cyclooctyloxymethyl, 1-cyclooctyloxy-ethyl, 2-cyclooctyloxy-ethyl, 1-cyclooctyloxyprop-1-yl, 2-cyclooctyloxy-propyl-l, 3-cyclooctyloxyprop-1-yl , 1-cyclooctyloxy-but-l-yl, 2-cyclooctyloxy-but-1-yl, 3-cyclooctyloxy-but-l-yl, 4-cyclooctyloxy-butyl-1-yl, l-cyclooctyloxy-but-2-yl , 2-cyclooctyloxy-but-2-yl, 3-cyclooctyloxy-but-2-yl, 3-cyclooctyloxy-but-2-yl, 4-cyclooctyloxy-but-2-yl or, 1- (cyclooctyloxymethyl) -et-1-yl, 1- (cyclooctyloxymethyl) -l- (CH 3) -et-1-yl or 1- (cyclooctyloxymethyl) prop-1-yl, especially C 3 -C6-cycloalkoxymethyl or 2- (C3-C6-cycloalkoxy) ethyl.
By "3- to 7-membered heterocycly" is meant both saturated, partially or completely unsaturated heterocycles, as well as aromatic heterocycles with one to three heteroatoms, selected from a group encompassing - one to three nitrogen atoms, - one or two sulfur atoms.
Examples of saturated heterocycles which may contain a mem-ber ring carbonyl or thiocarbonyl, are: oxiranyl, thiiranyl, aziridin-1-yl, aziridin-2-yl, diaziridin-1-yl, diaziridin-3-ils , oxetan-2-yl, oxetan-3-yl, tie-tan-2-yl, tietan-3-yl, acetidin-1-yl, acetidin-2-yl, aceti-din-3-yl, tetrahydrofuran-2 -yl, tetrahydrofuran-3-yl yl tetrahidrotiophen-2yl tetrahidrotiophen-3-yl pyrrolidin-1-yl-pyrrolidin-2,,,,, pyrrolidin-3-yl, l, 3-dioxolan-2 -yl, 1,3-dioxo-lane-4-yl, l, 3-oxathiolan-2-yl, l, 3-oxathiolan-4-yl, 1,3-oxathio-lane-5-yl, 1, 3 -oxazolidin-2-yl, 1,3-oxazolidin-3-yl, 1,3-oxazo-lidin-4-yl, 1,3-oxazolidin-5-yl, 1,2-oxazolidin-2-yl, 1 , 2-oxa-zolidin-3-yl, 1,2-oxazolidin-4-yl, 1,2-oxazolidin-5-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl , pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-5-yl, tetrahydropyrazole-1-yl, tetrahydropyrazole-3-yl, tetrahydropyrazole-4-yl, tetrahydropyran-2-yl, tetrahydropyran-3 -yl, tetrahydropyran-4-yl, tetrahydrothio pi-ran-2-yl, tetrahydrothiopyran-3-yl, tetrahydropyran-4-yl, pipe-ridin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, l, 3- dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dio-xan-2-yl, 1,3-oxatiane-2-yl, l, 3-oxatian-4-yl, 1,3-oxa-thian-5-yl, 1,3-oxatian-6-yl, 1,4-oxatian-2-yl, 1,4-oxa-tian-3- yl, morpholin-2-, morpholin-3-yl, morpholin-4-yl, hexahidropiridacin-1-yl, hexahidropiridacin-3-yl, hexahidrspirida-cin-4-yl-1-yl hexahydropyrimidin, hexahidropirimidin- 2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, pipera-cin-1-yl, piperazin-2-yl, piperazin-3-yl, hexahydro-l, 3,5-triazin-l- ilo, hexahydro-l, 3,5-triazin-2-yl, oxe-pan-2-yl, oxepan-3-yl, oxepan-4-yl, tiepan-2-yl, tie-pan-3-yl, tiepan-4-yl, 1,3-dioxepan-2-yl, 1,3-dioxepan-4-yl, 1,3-dioxepan-5-yl, 1,3-dioxepan-6-yl, l, 3- ditiepan-2-yl, l, 3-dithiepan-2-yl, l, 3-dithiepan-2-yl, l, 3-dithiepan-2-yl, 1,4-dioxepan-2-yl, 1, 4- dioxepan-7-yl, hexahydroazepin-1-yl, hexahydroazepin- 2-yl, hexahydroazepin-3-yl, hexahydroaze-4-yl, hexahydro-l, 3-diazepin-1-yl, hexahydro-1,3-diaze-2-yl, hexahydro-l, 3- diazepin-4-yl, hexahydro-l, 4-diaze-1-yl and hexahydro-1,4-diazepin-2-yl.
Examples of unsaturated heterocycles, which may contain an annular carbonyl or thiocarbonyl member, are: dihydrofuran-2-yl, 1,2-oxazolin-3-yl, 1,2-oxazolin-5-yl, 1, 3- oxazolin-2-yl;
Among the heteroatoms, the five- and six-member members are preferred, ie, preferably, eg.
nyl and 3-thienyl, pyrrolyl, such as, for example, 2-pyrrolyl and 3-pyrrolyl, isoxazolyl, such as, for example, 3-isoxazolyl, 4-isoxazolyl and 5-isoxazolyl, isothiazolyl, eg 3 -isotiazolilo, 4-and 5-isotia- zolilo isotxazolilo, pyrazolyl, 3-pyrazolyl as eg 4-pyrazolyl and 5-pyrazolyl, oxazolyl such as 2-oxazolyl eg, 4-oxazolyl and 5-oxazolyl , thiazolyl, such as 2-thiazolyl eg, 4-thiazolyl and 5-thiazolyl, imidazolyl, 2-imidazolyl as eg 4-imidazolyl and, oxadiazolyl, eg 1,2, 4-oxadiazol 3-yl, l, 2,4-oxadiazol-5-yl and 1,3, -oxadiazol-2-yl, thiadiazolyl, such as, for example, 1,2,4-thiadiazol-3-yl, 1, 2, 4-thiadiazol-5-yl and 1,3,4-thia-diazol-2-yl, triazolyl, such as, for example, 1,2,4-triazol-1-yl, 1,4-triazole-3 -yl and 1, 2, 4-triazol-4-yl, pyridinyl, such as, for example, 2-pyridinyl, 3-pyridinyl and 4-pyridinyl, pyridazinyl, such as, for example, 3-pyridazinyl and 4-pyridazinyl, pyrimidinyl , such as, for example, 2-pyrimidinyl, 4-pyrimidinyl and 5-pyrimidinyl, in addition, 2-pyrazinyl, 1, 3,5-triazin-2-yl and 1, 2,4-triazin-3-yl or, especially pyridyl, pyrimidyl, furanyl and thienyl.
All phenyl, carbocyclic and heterocyclic rings are preferably unsubstituted.
With respect to their use of the 3- (benzazol-4-yl) pyridinomenate I derivatives as herbicides, those compounds I are preferred, in which the variables have the following meanings, namely, by themselves or in combination:
X oxygen;
R1 hydrogen, airu.no or C? -C6-alkyl, especially hydrogen or C? -C4-alkyl, most preferably hydrogen or methyl;
R2 hydrogen, halogen, C6C6alkyl, C6C6 haloalkyl or. C? -C6-alkylsulfsnyl, especially trifluoromethyl;
R3 hydrogen;
R4 hydrogen, fluoro or chloro;
R5 cyano or halogen, especially chloro;
= Y-
R6 C? -C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C? -C6-alkylsulfonyl, (C? -C6-alkyl) carbonyl, (C? -C6-alkyl) thiocarbonyl, ( C6-C6-alkoxycarbonyl or C6-Cg-alkyl, which may be substituted by cyano, (C6-C6-alkoxy) carbonyl, di (C6-C6-ally C6-C6-alkyl, C3-C6-alkynyl, C? -C6-alkylsulfonyl or (C-C6-alkoxy) carbonyl.
The 3- (benzazol-4-yl) pyrimidinedione derivatives are most preferred. { = I with X = oxygen, R1 = methyl, R2 = trifluoromethyl, R3 = hydrogen, R4 = fluoro, R5 = chloro e = Y- = = C (ZR7) -N (CH3) -}
especially, the following compounds Ia.l to 272;
Table 1
In addition, the 3- (benza-zol-4-yl) pyrimidinedione derivatives of the formulas Ib to Ih, especially
- the compounds Ib.l-Ib.272, which differ from the corresponding compounds Ia.l-la.272, only in that R4 means hydrogen:
ZR7
the compounds Ic.l-lc.272, which differ from the corresponding compounds Ia.l-la.272 only in that R1 signifies hydrogen:
ZR7
the compounds Id.l-Id.272, which differ from the corresponding compounds Ia.l-la.272 only in that R1 and R4 means hydrogen:
the compounds Ie.l-le.272, which differ from the corresponding compounds Ia.l-la.272 only in that Y means = C (ZR7) -N (S02CH3) -:
ZR7
compounds If.l - If.272, which differ from the corresponding compounds Ia.l-la.272 only in that R4 means hydrogen and Y means = C (ZR7) -N (S02CH3) -:
ZR7 responding compounds Ia.l-la.272 only in that R1 means hydrogen and Y means = C (ZR7) -N (S0CH3) -:
the compounds Ih.l-Ih.272, which differ from the corresponding compounds Ia.l-la.272 only in that R1 and R4 signifies hydrogen and Y signifies = C (ZR7) -N (S02CH3) -:
ZR7
the compounds Ii.l-Ii.272, which differ from the corresponding compounds Ia.l-la.272 only in that = Y-means = C (ZR7) -0-:
the compounds I.l-Ik.272, which differ from the corresponding compounds Ia.l-la.272 only in that = Y-means = C (ZR7) -0- and R4 means hydrogen:
- the compounds Im.l-Im.272, which differ from the corresponding compounds Ia.l-la.272 only in that Y means = C (ZR7) -0- and R1 signifies hydrogen:
the compounds In.l-In.272, which differ from the corresponding compounds Ia.l-la.272 only in that Y means = C (ZR7) -0- and R1 and R4 means hydrogen:
The 3- (benzazol-4-yl) pyrimidinedione derivatives of the formula I can be obtained by different methods, for example, one of the following:
Method A): Reaction of a 3- (benzazol-4-yl) pyrimidinedione derivative I, wherein R 1 signifies hydrogen, with a compound II in a manner known per se:
L 1 denotes a customary cleavable group, such as, for example, halogen, preferably chlorine, bromine or iodine, (allogeneic) alkylsulfonyloxy, preferably methylsulfonyloxy or trifluoromethylsulfonyloxy, arylsulfonyloxy, preferably toluenesulfonyloxy, and alkoxysulfonyloxy, preferably methoxysulphonyloxy or ethoxysulfonyloxy.
It is usual to work in an inert organic solvent, for example in a protic solvent, such as, for example, lower alcohols, preferably in methanol or ethanol, if desired, in a mixture with water, or in an aprotic solvent, e.g. in an aliphatic or cyclic ether, such as, for example, methyl-tert-butyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, in an aliphatic ketone, such as, for example, acetone, diethyl ketone and ethyl methyl ketone, in an amide , such as, for example, dimethylformamide and N-methylpyrrolidone, in a sulfoxide, such as, for example, dimethyl sulfoxide, in a urea, such as, for example, tetramethylurea and 1,3-dimethyltetrahydro-2 (lH) -pyrimidinone. , in a carboxylate, such as, for example, ethyl acetate, or in a halogenated aliphatic or aromatic hydrocarbon, such as, for example, dichloromethane, dichloroethane, chlorobenzene and the dichlorobenzenes.
If desired, it is possible to work in the presence of a base, with inorganic bases, for example carbonates, such as sodium carbonate and potassium carbonate, hydrogen carbonates, such as hydrogen carbonate, for example, being suitable. sodium and potassium hydrogencarbonate, or alkali metal hydrides, such as, for example, sodium hydride and potassium hydride, as well as organic bases, eg amine, s, as P-ex. triethylamine, pyridine and N, N-diethylaniline, or alcoholates of alkali metals, such as, for example, sodium methanolate, sodium ethanolate and tere. potassium butanolate.
In each case, the molar quantity is preferably, with respect to the quantity of the starting compounds I (with R1 = hydrogen).
Generally, the reaction temperature ranges from 0 ° C to the boiling temperature of the reaction mixture, especially from 0 to 60 ° C.
A preferred variant consists of alkylating the salt obtained from the IV cyclization according to Method D) with R1 = H or V with R1 = H, without isolation from the reaction mixture, which still contains excessive base, eg. Sodium hydride, sodium alcoholate or sodium carbonate.
In case the salts can not be prepared by the cyclization described as method D), the salts of those compounds I, in which R 1 signifies hydrogen, can also be obtained in a known manner from the process products of the Cj methods. to Fj. For this purpose, for example, the aqueous solution of an inorganic or organic base is mixed with the derivative of 3- (benzazol-4-yl) pyrimidinedione I, in which R 1 signifies hydrogen. The salt formation normally takes place at 20 to 25 ° C with sufficient velocity.
It is particularly favorable to prepare the sodium salt by dissolving the 3- (benzazol-4-yl) pyrimidinedione derivative I with R 1 = hydrogen in an aqueous solution of sodium hydroxide at 20 to 25 ° C, with approximately equimolar amounts of the derivative being used. of 3- (benzazol-4-yl) pyrimidinedione I (with R1 = H) and sodium hydroxide. The corresponding salt of the 3- (benzazol-4-yl) pyrimidinedione derivative I can then be isolated, eg, by precipitation with a suitable inert solvent or evaporation of the solvent.
The salts of the 3- (benzazol-4-yl) pyrimidinedione-a derivatives, whose metal ion is not an alkali metal ion, can be obtained, generally, by recrystallization of the corresponding alkali metal salts in aqueous solution; the same goes for the ammonium-, phosphonium, sulphonium and sulfoxonium salts through ammonia, phosphonium, sulfonium or sulfoxonium hydroxides.
Method B Reaction of a 3- (benzazol-4-yl) pyrimidinedione derivative of the formula I, wherein R 1 signifies hydrogen, with an electrophilic amination reagent, in the presence of a base:
As an amination reagent, 2,4-dinitrophenoxyamine has been especially proven, but it is also possible to use, for example, hydroxylamine-O-sulfonic acid (HOSA), which is already known from the literature as an amination reagent (see eg E. Hofer et al., Synthesis 1983, 466, W. Friedrichsen et al., Heterocycles 20 (1983) 1271, H. Hart et al., tetrahedron Lett 25 (1984) 2073, B. Vercek et al. al., Monatsh, Chem. 114 (1983) 789; G. Sosnousky et al., Z. Naturforsch. 738 (1983) 884; RS Atkinson et al., J. Chem. Soc. Perkin Trans. 1987, 2787).
The amination can be carried out in a manner known per se (see, for example, T. Sheradsky, Tetrahedron Lett, 1968, 1909, MP Wentland et al., J. Med. Chem. 27 (1984) 1103 and especially EP. -A 240 194, EP-A 476 697 and EP-A 517 181, where the amination of uracils is taught).
Normally, the reaction is carried out in a polar solvent, for example in dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide or in ethyl acetate, which has hitherto been shown to be particularly suitable.
Suitable bases are, for example, alkali metal carbonates, such as, for example, potassium carbonate, alkali metal alcoholates, such as, for example, sodium methylate and potassium tert-butolate, or alkali metal hydrides. , such as, for example, sodium hydride.
The amount of base and amination agent is preferably 0.5 to 2 times the molar amount, based on the starting compound.
Method C Sulfurization of a 3- (benzazol-4-yl) pyrimidinedione derivative of the formula I, wherein X means oxygen:
The sulfurization is generally carried out in an inert solvent or diluent, for example, in an aromatic hydrocarbon, such as, for example, toluene and the xylenes, in an ether, such as, for example, diethyl ether, 1,2-dimethoxyethane and tetrahydrofuran, or in an organic amine, such as, for example, pyridine.
Suitable sulfurization reagents are, in particular, phosphorus sulfide (V) and 2,4-bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphetane-2,4-dithione (reagent from "Lawesson") ).
Generally, it is sufficient to use the molar amount or 5 times the molar amount, with respect to the starting compound to be sulfided, to obtain a substantially complete transformation.
The reaction temperature normally varies from 20 to 200 ° C, preferably from 40 ° C up to the boiling temperature of the reaction mixture.
Cyclization of an arylurea of the formula III or an aryl of the formula IV in the presence of a base:
I (X = O)
L2 means lower molecular weight alkyl, preferably C? -C4 alkyl, or phenyl.
As a rule, it is cyclized in an inert organic solvent or diluent, which is aprotic, for example, in an aliphatic or cyclic ether, such as, for example, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, in an aromatic, such as p. Examples of these are, for example, benzene and toluene or in a polar solvent, such as, for example, dimethylformamide and dimethyl sulfoxide. Mixtures of polar solvent and a hydrocarbon, such as, for example, n-hexane, may also be suitable. Depending on the starting compound, water can also be used as the solvent.
Suitable bases are, preferably, alkali metal alcoholates, especially sodium die alcoholates, alkali metal hydroxides, especially sodium hydroxide and potassium hydroxide, alkali metal carbonates, especially sodium carbonate and potassium carbonate, and metal hydrides, especially Sodium hydride When sodium hydride is used as a base, it has proven advantageous to work in an aliphatic or cyclic ether, in dimethylformamide or in dimethyl sulfoxide.
e a ase, with respect to a can e e for the success of the reaction.
Generally, the reaction temperature varies from (-78) ° C to the boiling temperature of the corresponding reaction mixture, especially from (-60) to 60 ° C.
When R1 in formula III or IV means hydrogen, then a metal salt is obtained as a process product, the metal corresponding to the cation of the base used. The salt can be isolated and purified in a known manner, or transformed, if desired, by an acid in the free compound I with R1 = hydrogen.
Method E Treatment of a substituted 2-aminoaniline Va with nitrous acid
Go I { = Y- = = N-N (R6) -}
The cyclization reaction can be carried out by known methods (see, eg Houben-Weyl, Methoden der organischen Chemie, Georg Thieme Verlag Stuttgart, Vol. E8d, 1994 edition, pp. 409-415).
The reaction is preferably carried out in an acidic, aqueous medium, but also in lower carbonylic acids, such as P-ex. acetic acid, are suitable diluents. Suitable aqueous base solvents are especially dilute mineral acids, for example. example, 10% hydrochloric acid.
The nitrous acid is advantageously prepared in situ by adding an alkali metal nitrite - in the absence of solvent or as an aqueous solution - to the reaction mixture which is composed of diaminobenzene in aqueous solution, acid or in a carboxylic acid.
specific to mind, 0 to, very specific to, approx. .
Conveniently, the educts are used in approximately stoichiometric amounts, or an excess of the theoretically expected amount in nitrous acid of 10 mol% is used, at most.
Analogously, the following intermediate product can be cyclized:
VI VII
Method F) Condensation of a substituted 2-aminophenol, 2-aminothiophenol or 2-aminoanilines (V) with carbonic acid or carboxylic acid derivatives:
I (Z = chemical bond, O, NH, R7 = H, optionally alkyl, alkenyl or aryl) The condensation reaction of the bifunctional benzenes V with the carbonic acid or carboxylic acid derivatives is carried out in a manner known durchgeführt (see eg Houben-Weyl, Methoden der organischen Chemie, Georg Thieme Verlag Stuttgart, Vol. E8c, the 1994 edition, pp. 247-284; vol.E8b, the 1994 edition, pp. 881- 901; vol E8a, 1993 edition, pp. 1032-1078). Preferred carbonic acid or carboxylic acid derivatives are anhydrides, acid chlorides, orthoesters, diimides, nitriles, trichloromethyl substituted compounds, isocyanates or their yanates and their thio analogs.
organic solvents, for example, aromatic hydrocarbons, such as, for example, benzene, toluene and o-, m-, p-xylene, halogenated hydrocarbons, such as, for example, methylene chloride, chloroform and dichloroethane, lower alcohols, such as ethanol, ethanol, aliphatic or cyclic ethers, such as, for example, dimethoxyethane, tetrahydrofuran and dioxane, carboxylate, such as, for example, ethyl acetate or polar aprotic solvents, such as, for example, dimethylformamide and dimethyl sulfoxide.
The reaction can be accelerated, if desired, by the addition of catalytic amounts of an acid. Suitable acids are, in particular, mineral acids, such as, for example, hydrochloric acids or sulfonic acids, such as, for example, p-toluenesulfonic acid. The amounts of acid are preferably 0.1 to 5 mol%, based on the amount of V.
The reaction temperatures preferably range from 20 ° C to the reflux temperature of the reaction mixture, especially from 60 ° C to the reflux temperature.
The carbonic acid or carboxylic acid derivative is used, or in amounts of approx. stoichiometric or in excess. In appropriate cases a larger excess can be used or it can be worked without solvent. Preferably, approximately stoichiometric amounts or an excess of up to 10 mol equivalents, with respect to the amount of V, will be used.
The 2-aminophenols, 2-thiophenoleans and substituted 2-anilines (V) are advantageously obtained by reduction of 2-nitrophenols, 2-thiophenols or 2-anilines corresponding to VIII (see, for example, Houben-Weyl, Methoden der organischen Chemie, Georg Thieme Verlag Stuttgart, Volume XI / 1, 4th edition 1957, pp. 431 f.):
I am a e ementa e, as eg. erro, is a o and zinc, - hydrogen in the presence of suitable catalysts, such as eg palladium or platinum on carbon or Raney nickel, or complex hydrides, such as, for example, LiAlH4 and NaBH, optionally in the presence of catalysts.
Suitable solvents are generally, according to the reducing agent, carboxylic acids, such as, for example, acetic acid and propionic acid, alcohols, such as, for example, methanol and ethanol, ethers, such as, for example, diethyl ether. ether, methyl tert. -butyl ether, tetrahydrofuran and dioxane, aromatics, such as, for example, benzene and toluene, as well as mixtures of such solvents.
The reactions can be carried out at temperatures of (-100) ° C up to the boiling temperature of the corresponding reaction mixture.
Commonly, the starting compounds are used in amounts of approx. stoichiometric; in individual cases it may be advantageous to use an excess of the one or the other component of approx. 10% in mol.
The 2-nitrophenols, -thiophenols and -anilines VIII, on the other hand, can be liberated from the corresponding nitro-protected compounds IX:
protection = usual protecting group protecting phenols or thiophenols as ethers or amino groups as amide.
. . tive Groups in Organic Synthesis, John Wiley & Sons, Inc., 2a. 1991 edition, pgs. 145 and next and pages. 279 and next ).
Suitable separating reagents are, in particular: in the case of alkylphenols: trimethylsilyl iodide, boron tribromide, boron trichloride, aluminum trichloride, lithium chloride or hydrogen bromide; in the case of the benzylphenols or substituted benzylthiophenols: voro trifluoride hydrofluoric acid or hydrogen / catalyst, preferably a noble metal catalyst, such as, for example, palladium or platinum.
As the solvent / diluent, one must be chosen which is inert to the corresponding separation reagent. When the halides, trimethylsilyl iodide, voro tribromide, boron trichloride or aluminum trichloride are used, halogenated solvents, such as, for example, dichloromethane, chloroform, carbon tetrachloride and dichloroethane, are especially preferred. Hydrogen bromide is preferably used in aqueous solution, very preferably as a 48% solution; the lithium chloride is preferably used in polar solvents, such as, for example, lower alcohols, dimethyl sulfoxide and dimethylformamide; Hydrogenolytic methods are preferably used in lower alcohols or carboxylic acids, optionally with the addition of a hydrogen transducer, such as, for example, cyclohexene and cyclohexanediene.
The temperature for the separation reaction preferably varies from 0 ° C to the boiling temperature of the corresponding reaction mixture.
The separation reagent is preferably used in stoichiometric or excess amounts. The excess fluctuates, especially, between one and ten mol equivalents, with respect to the amount of IX.
Finally, the nitro-protected compounds IX can be prepared in a manner known per se by nitration of phenols, thiophenols or anilines (protected) x (see, for example, Houben-Weyl, Methoden der or-p gs., And s.
Suitable nitrating reagents are, in particular, nitric acid in a mixture with sulfuric acid or acetic anhydride, or nitronium salts, especially nitronium tetrafluoroborate. Composite mixtures of nitric acid and sulfuric acid may consist of arbitrary quantitative relationships of the two mixing components; those mixtures are preferred, in which the part of sulfuric acid strongly predominates or where it serves as a solvent. For the mixture of nitric acid and acetic anhydride, the same applies analogously. The nitronium tetrafluoroborate is preferably used in aprotic, polar solvents, for example in acetoneitrile or nitromethane.
The reaction temperature varies, generally, from (-80) to 80 ° C, especially from (-20) ° C to 30 ° C.
In nitrations with the nitric acid reagent it is preferred to work with an armoximously equimolar amount, or very preferably, with an excess of the nitrating reagent. The excess may amount to multiple times the amount of X. The nitronium tetrafluoroborate is preferably used in quantity with respect to the substrate or in a slight excess of between 1.1 and 1.5 mole equivalents.
Analogously, the following intermediate products can be nitrated:
The 3- (benzazol-4-yl) pyrimidinedione derivatives of the formula I with one or more centers of chirality are generally obtained as enantiomeric or diastereomeric mixtures, which, if desired, are separated by conventional methods for this. end, eg by crystallization or chromatography on an optically active adsorbate, on the substantially pure isomers. The optically active isomers can be prepared, advantageously, from the corresponding optically active starting materials.
Those derivatives of 3- (benzazol-4-yl) pyrimidinedione of the formula I, in which R 1 signifies hydrogen, can be transformed in a manner known per se into their salts (cf. the explanations of the Method)).
The arylurof formula III are new. They can be obtained according to methods known per se, eg using the following method:
Method G) Reaction of a β-ketocarboxylate XIII with a urea XIV:
XIII XIV
III L2 means lower molecular weight alkyl, preferably C? -C4 alkyl, or phenyl.
Preferably, working is carried out under essentially anhydrous conditions in an inert solvent or diluent, most preferably in the presence of an acid or basic catalyst.
As the solvent or diluent, organic solvents which are miscible with water with water in the form of azeotropes, for example aromatics, such as, for example, benzene, toluene and o-, m-, p-xylene, halogenated hydrocarbons, are particularly suitable. , such as, for example, methylene chloride, chloroform, tetraclo-rokohlenstoff and chlorobenzene, aliphatic and cyclic ethers, such as, for example, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, or cyclohexane, but also alcohols, such as, for example, methanol and ethanol.
Suitable acid catalysts are preferably strong mineral acids, such as, for example, sulfuric acid and hydrochloric acid, phosphorus-containing acids, such as, for example, orthophosphoric and polyphosphoric acid, organic acids, such as, for example, p-toluenesulfonic acid, as well as acid cation exchangers, such as, for example, "Amber-lyst 15" (Cia. Fluka).
e me a es a ca nos, as eg. r, especially, the alkali metal alcoholates, such as, for example, sodium methanolate and sodium ethanolate.
Conveniently, XIV and β-ketocarboxylate XIII are reacted in approximately stoichiometric amounts or a slight excess of one or the other component of ca. 10% in mol.
Normally, it is sufficient to use a catalyst amount of 0.5 to 2 mol%, with respect to the amount of one or the other of the starting compounds.
Generally, the reaction is carried out at a temperature of 60 to 120 ° C, to rapidly remove the water formed, preferably, it is carried out at the boiling temperature of the reaction mixture.
Method H) Reaction of an enol ether XV with a urea XVI:
XV XVI
III L2 and L3 each represent lower alkyl, preferably C, -C4-alkyl, or phenyl.
The reaction is preferably carried out in an inert organic solvent, miscible with water, for example an aliphatic or cyclic ether, such as, for example, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, or a lower alcohol, especially ethanol, They have, preeren tly, aa empera ura eeuca meczla of reaction.
However, the reaction can also be carried out in an aromatic diluent, such as, for example, benzene, toluene and o-, m-, p-xylene, in which case it is advisable to add an acid catalyst, such as, for example, hydrochloric acid and p-toluenesulfonic acid, for example an alkali metal alcoholate, such as, for example, sodium methanolate and sodium ethanolate. Also in this variant, the reaction temperature rises, usually at 50 to 100 ° C, preferably at 60 to 80 ° C.
With respect to quantitative relationships, the indications for method G) are valid.
Method J Reaction of an enamino ester XVII with an isocyanate XVIII:
XVII XVIII III
L2 means lower molecular weight alkyl, preferably C? -C4 alkyl, or phenyl.
Conveniently, the reaction is carried out in the presence of an organic, aprotic, essentially anhydrous solvent or diluent, for example an aliphatic or cyclic ether, such as, for example, diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, an aliphatic hydrocarbon. or aromatic, such as, for example, n-hexane, benzene, toluene and o-, m-, p-xylene, a halogenated aliphatic hydrocarbon, such as, for example, methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane and chlorobenzene, an aprotic, polar solvent, such as, for example, dimethylformamide, hexamethylphosphoric acid triamide and dimethyl sulfoxide, or a mixture of the solvents mentioned.
If desired, it is also possible to work in the presence of a metal hydride base, such as, for example, sodium hydride and potassium hydride or a tertiary organic base, such as.
Conveniently, the educts are reacted in stoichiometric quantities or a slight excess of one or the other component of ca. 10% in mol. When working without solvent in the presence of an organic base, this is present in a greater excess.
The reaction temperature varies, preferably from (-80) to 50 ° C, especially from (-60) to 30 ° C.
In an especially preferred variant, the ester III ester is converted to the excessive base directly (ie "in situ") according to method D) in the product of corresponding value I.
Method Kj Reaction of an enamin ester XVII with a urethane XIX:
XVII XIX III
L2 and L4 independently represent a low molecular weight alkyl, preferably C? -C4 alkyl, or phenyl.
This reaction is conveniently carried out in a polar aprotic solvent or diluent, such as, for example, dimethylformamide,
2-butanone, dimethyl sulfoxide and acetonitrile, and advantageously, in the presence of a base, for example, an alkali metal or alkaline earth metal alcoholate, in particular sodium alcoholate, such as, for example, sodium methanolate, a metal carbonate alkaline or alkaline earth metal, especially sodium carbonate, or an alkali metal hydride, such as, for example, lithium hydride and sodium hydride.
Normally, it is sufficient to use a quantity 1 to two times molar of the base, with respect to the amount of XVII or XIX.
, pree in emen e ra tion of the reaction mixture.
With respect to the quantitative relationships of the starting compounds, the indications for method G) are valid.
In a particularly preferred variant, a sodium alcoholate is used as the base and the alcohol formed is continuously distilled in the course of the reaction. The thus obtained IV esters can be cyclized without isolation from the reaction mixture according to method D) in the salt of the substituted benzthiazole I (with R1 = H).
The urethanes XIX, for their part, can be prepared, for example, from carbon dioxide chloride XX and anilines XXI:
XX XXI XIX
To avoid an excess of aniline, generally, an auxiliary base, such as, for example, triethylamine, pyridine or the alkali metal carbonates has to be added to capture the hydrogen chloride formed in the reaction. Pyridine is found to be especially suitable, and can be used simultaneously as a solvent.
In addition to pyridine, aromatic hydrocarbons, such as, for example, benzene, toluene and o-, m-, p-xylene, halogenated hydrocarbons, such as, for example, methylene chloride, chloroform and dichloroethane, lower alcohols, such as, for example, methanol and ethanol, aliphatic or cyclic ethers, such as, for example, dimethoxyethane, tetrahydrofuran and dioxane, carboxylates, such as, for example, ethyl acetate, or aprotic solvents polar, such as, for example, dimethylformamide and dimethyl sulfoxide.
The reaction temperature generally ranges from 0 ° C to the reflux temperature of the corresponding reaction mixture.
approx. This is not possible, or there is a carbonic excess of, at most, 10 percent in mol.
As an auxiliary base it is usually used, in an amount of approximately, equimolar - with respect to the quantity of XX or XXI - or in an exseco of approx. 2 times the molar amount. When pyridine is used as an auxiliary base, then it is advisable to use an even greater excess, in which case it is possible to work without additional solvent.
Method L) Reaction of an isocyanate XXII with an aniline derivative XXI:
XXII XXI III (R1 = H)
L2 means lower molecular weight alkyl, preferably C? -C4 alkyl, or phenyl.
This reaction is conveniently carried out in an organic, aprotic, substantially anhydrous solvent or diluent, for example in the presence of an aliphatic or cyclic ether, such as, for example, diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, aliphatic or aromatic hydrocarbon, such as, for example, n-hexane, benzene, toluene or-, m-, p-xylene, a halogenated aliphatic hydrocarbon, such as, for example, methylene chloride, chloroform, carbon tetrachloride, 1,2- dichloroethane and chlorobenzene, an aprotic, polar solvent, such as, for example, dimethylformamide, hexamethylphosphoric acid triamide and dimethyl sulfoxide, or a mixture of the solvents mentioned.
If desired, it is also possible to work in the presence of a metal hydride base, such as, for example, sodium hydride and potassium hydride, an alkali metal or alkaline earth metal alcoholate, such as, for example, sodium methanolate, ethanolate of sodium and potassium tert-butanolate, or a nitrogenous organic base, such as, for example, triethylamine and pyridine, the organic base being used at the same time as a solvent.
This method allows you to use your computer in an excess of aprsx. 20% in mol. When working without solvent in the presence of an organic base, then this is advantageously present in an even greater excess.
The reaction temperature varies, generally, from (-80) to 150 ° C, preferably from (-30) ° C to the boiling temperature of the corresponding reaction mixture.
The arylanilides of the formula IV are also new; they can also be prepared in a manner known per se, for example, by reacting an amide XXIII with a urethane XXIV according to the method M):
XXIII IV (R1 = H)
L2 means lower molecular weight alkyl, preferably C? -C4 alkyl, or phenyl.
The reaction is advantageously carried out in a substantially anhydrous solvent / diluent at normal pressure, very preferably in the presence of an acid catalyst.
In order to obtain the IV enamincarboxylates with R1 = amino, it is advisable to react the compounds XXIV with the protected amino group (eg as hydrazone).
Suitable solvents / diluents are, in particular, organic liquids miscible with water in azeotropic form, for example aromatics, such as, for example, benzene, toluene and o-, m-, p-xylene or the halogenated hydrocarbons, such as .ej carbon tetrachloride and chlorobenzene.
Suitable catalysts are, in particular, strong mineral acids, such as, for example, sulfuric acid, organic acids, such as, for example, p-toluenesulfonic acid, phosphorus-containing acids, such as, for example, orthophosphoric acid and poly-acid. - pe. "Amberlyst 15" (Cia. Fluka).
Generally, a reaction temperature of approx. 70 at 150 ° C; but in order to be able to quickly remove the reaction water formed, the reaction is conveniently carried out at the boiling temperature of the corresponding reaction mixture.
XXIII and XXIV are generally used in amounts of approx. stoichiometric; but preferably a slight excess of XXIV of ca. 20% in mol.
The amide XXIII can be prepared, eg in the following manner (method N)):
XXIII (R3 = H)
XXV XXI
The reaction is preferably carried out in an inert aprotic solvent, substantially anhydrous, for example in a halogenated hydrocarbon, such as, for example, methylene chloride, chloroform, carbon tetrachloride and chlorobenzene, an aromatic hydrocarbon, such as, for example, benzene. , toluene and o-, m-, p-xylene, or an aliphatic or cyclic ether, such as, for example, diethyl ether, dibutyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane.
The reaction temperature varies, generally, from approx. 70 to 140 ° C, especially 100 to 120 ° C.
XXV and XXI are usually used in arpox quantities. stoichiometric, or the one or the other component is used in excess of approx. 10% in mol.
er va os e an na seg n e m):
XXI XVIII
The method can be carried out in an inert diluent or diluent, substantially anhydrous or without solvent, the aniline derivatives XXI, preferably with phosgene, being converted into a "phosgene equivalent", such as, for example, diphosgene, triphosgene and carbonyldiimidazole or with chloroformate. trichloromethyl.
Examples of suitable solvents or diluents are organic solvents, aprotic solvents, for example dimethylformamide or aromatics, such as, for example, toluene and o-, m-, p-xylene, halogenated hydrocarbons, such as, for example, methylene chloride, chloroform, 1,2-dichloroethane and chlorobenzene, aliphatic or cyclic ethers, such as, for example, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, or esters, such as, for example, ethyl acetate, as well as mixtures of these solvents.
Conveniently, the educts are used in amounts of approx. stoichiometric, or the one or the other component is used in an excess of approx. 200% in mol.
According to the aniline derivative XXI formed, it may be advantageous to add a base, such as, for example, triethylamine, in an amount of 0.5 to 2 molar times, with respect to the quantity of XXI.
The reaction temperature generally ranges from (-20) ° C to the reflux temperature of the corresponding solvent or solvent mixture.
The aniline derivatives XXI in turn can be obtained in a manner known per se (see, for example, Houben-Weyl, Methoden der organischen Chemie, Georg Thieme Verlag Stuttgart, Volume XI / 1, 4th edition 1957, pp. 431 and sig.) by reduction of the corresponding XXVI nitrogenous derivatives:
With regard to the reductant, solvent, reaction temperatures and quantitative ratios, refer to the indications for method F).
Compounds XXVIII and XXI may also contain one or more centers of chirality and are generally obtained as enantiomeric or diastereomeric mixtures. The mixtures can be separated, if desired, by methods customary for this purpose, eg by crystallization or chromatography on an optically active adsorbate, in the substantially pure isomers. The pure active isomers can also be obtained from the corresponding optically active starting materials.
Unless otherwise indicated, all the methods described above are used, suitably, under atmospheric pressure or under the proper pressure of the corresponding reaction mixture. Generally, the reaction components are used in a molar ratio of 0.95: 1 to 5: 1.
Further processing of the reaction mixtures can generally be carried out by methods known per se, for example by dilution of the reaction solution with water and subsequent isolation of the product by filtration, crystallization or extraction of the solvent, or by elimination of the solvent, distribution of the residue in a mixture from water and an appropriate organic solvent and further elaboration of the organic phase, giving the product.
The compounds I and their salts useful for agriculture are suitable, both in the form of isomeric mixtures, and also in the form of pure isomers, and as herbicides. Herbicidal products containing i are well suited to combat the growth of unwanted plants in areas not intended for cultivation, especially in high application quantities. In crops, such as wheat, rice, corn, soybeans and cotton, they are active against harmful grasses and gamines, without causing damage worthy of mention in the crop plants. This effect occurs mainly with low amounts of application.
They are compounds I or in the products that I use in additional plant crops to eliminate unwanted plants there. For example, the following crops are included: Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus lemon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylestre, Ricinus communis, Saccharum officinarum, Sécale cereale , Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.
In addition, compounds I can also be used in crops which have been made tolerant to the action of herbicides by culture or genetic engineering methods.
The compounds I or the products containing them can be used, for example, in the form of aqueous solutions, powders directly sprayable suspensions, also in the form of suspensions, dispersions or emulsions aqueous, oily or other highly concentrated, dispersions of oil , pastes, spraying agents, dusting agents or granules, by means of spraying, spraying, sprinkling or sprinkling. The forms of application depend on the purpose of the use; In any case, they must guarantee the finest possible distribution of the active substances of the invention.
Suitable as inert auxiliaries are mineral oil fractions ranging from medium to high boiling point, such as kerosene or diesel oil, in addition, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, such as paraffin, tetrahydronaphthaline. alkylated naphthalenes or their derivatives, alkylated benzenes, non-cyan or exanone, or energetic vehicles, N-methylpyrrolidone or water.
Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders or granules dispersible in water by the addition of water. To obtain emulsions, pastes or oil dispersions, the substrates can be homogenized as such or dissolved in an oil or solvent, by means of humectants, adherents, dispersants or emulsifiers, in water. However, a humectant, adherent, dispersant or emulsifier and, optionally, a solvent or an oil, can also be prepared from the active substance, which can be diluted with water.
Suitable surface-active substances are: alkali metal, alkaline earth metal, ammonium salts of aromatic sulphonic acids, eg lignin sulphonic acid, phenolsulfonic acid, naphthalenesulfonic acid and dibutylnaphthalene sulfonic acid, as well as fatty acids, alkyl and alkylaryl sulfonates, sulfates of alkyether, lauryl ether and fatty alcohol, as well as salts of sulphonated hexa, hepta and octadecanols, as well as glycol ethers of fatty alcohol, sulfonated naphthalene condensates and their derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylenectyl-phenol ethers, isooctylphenol, octylphenol or nonylphenol ethoxylated, alkylphenol polyglycol ethers, tributylphenylpolyglycol ethers, alkylaryl polyether alcohols, isothri-decyl alcohol, condensates of fatty alcohol-ethylene oxide, castor oil ethoxylated, polyoxyethylene alkyl ethers, polyoxypropylene , acetal polyglycol ether lauryl alcohol, sorbitol esters, sulphite residual liquors and methylcellulose.
The spraying, spraying and atomizing agents can be obtained by mixing the active substances together with a solid support.
Granules, eg coated granules, impregnated granules and homogenous grains can be prepared by bonding the active substances with solid supports. Suitable solid supports are mineral earths, such as silica gel, silicic acids, silica gels, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastic, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as stone powders, bark powders of other solid supports.
The concentrations of active substances I in ready formulations can vary widely. The formulations generally contain from 0.001 to 98% by weight, preferably from 0.01 to 95% by weight of at least one active substance. The active substances are used in a purity of 90% bis 100%, preferably 95% up to 100% (according to NMR spectrum).
The following formulation examples illustrate the preparation of such preparations:
I. 20 parts by weight of compound No. 1 are dissolved in a mixture containing 80 parts by weight of alkylated benzene,
parts by weight of the addition product of 8 to 10 moles of ethylene oxide to 1 mole of oleic acid N-monoethanolamide, 5 parts by weight of the calcium salt ofdedecylbenzenesulfonic acid and 5 parts by weight of the product of adi - 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100 000 parts by weight of water and distributing it finely therein, an aqueous dispersion containing 0.02% by weight of the active substance is obtained.
II. 20 parts by weight of compound No. 2 are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the addition product of 7 moles of ethylene oxide to 1 mole of isooctylphenol and 10 parts by weight of the addition product of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100 000 parts by weight of water and distributing it finely therein, an aqueous dispersion containing 0.02% by weight of the active substance is obtained.
III. 20 parts by weight of the active substance No. 4 are dissolved in a mixture consisting of 25 parts by weight cyclohexanone, 65 parts by weight of a mineral oil fraction from the boiling point of 210 to 280 ° C and 10 parts by weight. by weight of the addition product of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100 000 parts by weight of water and distributing it finely therein, an aqueous dispersion containing 0.02% by weight of the active substance is obtained.
with 3 parts by weight of the sulfonated sodium sulphonates, 17 parts by weight of the sodium salt of a lignin sulphonic acid of a sulphite residual liquor and 60 parts by weight of pulverulent silica gel and milled in a hammer mill. By distributing the mixture finely in 20,000 parts by weight of water, a spray mixture containing 0.1% by weight of the active substance is obtained
V. 3 parts by weight of the active substance No. 8 are mixed with 97 parts by weight of finely particulate kaolin. In this way, a spray agent containing 3% by weight of the active substance is obtained.
SAW. 20 parts by weight of the active substance No. 12 are intimately mixed with 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol-polyglycol ether, 2 parts by weight of the sodium salt of a condensate of phenolsulfonic acid-urea-formaldehyde and 68 parts by weight of a paraffinic mineral oil. A stable oleic dispersion is obtained.
VII. 1 part by weight of compound 14 is dissolved in a mixture consisting of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of castor oil etc. Then, it can be diluted with water to the desired concentration. A stable emulsion concentrate is obtained.
VIII. 1 part by weight of compound 19 is dissolved in a mixture consisting of 80 parts by weight of cyclohexanone, 20 parts by weight of Wettol® EM 31 (nonionic emulsifier based on ethoxylated castor oil, BASF AG). Then, it can be diluted with water to the desired concentration. A stable emulsion concentrate is obtained.
The compounds I or the herbicidal products that contain them can be applied before or after emergence. When the active substances are less tolerated by the crop plants, then application methods may be used in which the herbicidal products are sprayed with the aid of spraying apparatus in such a way that they do not fall on the leaves of the sensitive crop plants , but only on the leaves of the unwanted plants that grow below the primes - ee, ay- and.
The amounts of application in active substance I amount, depending on the respective application end, of the time of year, the target plants and their growth stage, to 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (sa).
In order to broaden the spectrum of action and to achieve synergistic effects, the compounds I can be mixed with numerous representatives of other groups of hervicidal active substances and growth regulators and applied in conjunction with these. Suitable mixing components are, for example, 1,2,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anuides, (het) aryloxyalkanoic acids and their derivatives., benzoic acid and its derivatives, benzothiadiazinones, 2- (hetaroyl / aroyl) -1, 3-cyclohexandiones, hetaryl-aryl-ketones, benzisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilides, derivatives of cyclohexane-1, 3-dione, diacins, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofu-ran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, di-pyridyls, halogenated carboxylic acids and their derivatives, ureas, phenyluracils, imidazoles, imidazolinones, N-phe nyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and heteroaryloxyphenoxypropionates, phenylacetic acid and its derivatives, phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils.
In addition, it may be useful to apply the compounds I on their own or in combination with other herbicides also mixed with other phytosanitary products, for example products for combating phytopathogenic pests or fungi or bacteria. Also interesting is the miscibility with solutions of mineral salts, which are used to alleviate nutrient deficiencies or microelements. Non-phytotoxic oils and oil concentrates can also be used.
Example 1 3- [7-Chloro-5-fluoro-1-methyl-1H-benzotriazol-4-yl-1-methyl-6-trifluoromethyl-2- (4H, 3H) -pyrimidinedione (Compound 2)
To a mixture of 0.25 g 3- [7-chloro-5-fluoro-1-methyl-1H-benzotria-zol-4-yl-6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione, 0, 12 g of potassium carbonate and 20 ml of absolute dimethylformamide are added in drops at 20 ° C 0.12 g of methyl iodide. Then, it is stirred for 18 hours, after which the reaction mixture is mixed with 50 ml of water. Then, 20 ml of ethyl acetate are extracted three times with each time. The combined organic phases are dried and finally concentrated. The crude product is purified by chromatography on silica gel (eluent: cyclohexane / ethyl acetate = 1: 1). Yield: 0.07 g; iH-NMR (270 MHz, CDC13): d [ppm] = 7.45 (d, lH), 6.45 (s, lH), 4.55 (s, 3H), 3.60 (s, 3H).
EXAMPLE 2 3- [7-Chloro-5-fluoro-l-methyl-lH-benzotriazol-4-yl] -6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (Comp.1)
0.13 g of sodium methylate in 7 ml of absolute dimethylformamide are mixed under a nitrogen atmosphere at 0 ° C within 15 minutes with 0.43 g of ethyl 3-amino-4,4,4-trifluorobut-2-enoate in 3 ml of dimethylformamide. It is stirred, first, for an hour and a half at 10 ° C, after which a solution of 0.57 g of 7-chloro-5-fluoro-l-methyl is added to the reaction mixture in drops within 15 minutes. ethyl -lH-benzotriazol-4-yl-carbamate in 20 ml of dimethylformamide. It is then heated to 20 ° C and stirred for 5 minutes. The mixture is then heated to 60 ° C and mixed with 0.35 g of 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) Finally, it is stirred for 4 hours at 120 ° C and 18 hours at 20 ° C. For further processing, the mixture is poured into 100 ml of a 10% by weight aqueous solution of potassium, the valuable product is extracted with diethyl ether (twice 50 ml) and, after having regulated the Residual aqueous phase at a pH value of 1 is extracted with ethyl acetate (three times 30 ml) The combined organic phases are washed with approximately 20 ml of aqueous solution, saturated with sodium chloride and 30 ml of aqueous solution at room temperature. 10% by weight of lithium chloride, then dried over sodium sulfate and finally concentrated Yield: 0.25 g; H-NMR (250 MHz, in CDCl 3): d [ppm] = 10.25 (br, lH), 7.45 (d, lH), 6.30 (s, lH), 4.60 (s, 3H).
-c gold- - uoro- - r uoroace
To 100 g of 2-chloro-4-fluoroaniline in 800 ml of absolute diethyl ether are added in drops at 0 ° C 144.3 g of trifluoroacetic acid anhydride in 150 ml of diethyl ether. After heating to 20 ° C, the mixture is mixed with 500 ml of water. The organic phase is separated, washed three times with water, then dried over sodium sulfate and finally concentrated. Yield: 10 151.5 g; IFN-NMR (270 MHz, in CDC13): d [ppmj = 8.35 (br, lH), 8.25 (dd, lH), 7.20 (dd, lH), 7.05 (dt, lH).
Intermediate 2.2 15 3-chloro-5-fluoro-2-N-trifluoroacetylamino-nitrobenzene
To 75 g of 2-chloro-4-fluoro-N-trifluoroacetylaniline in 753 ml of acetic anhydride, 375 ml of 98% nitric acid are slowly added dropwise at (-5) ° C. Then stir for one hour at (-5) ° C, then
of which the mixture is heated to 20 ° C. The course of the reaction is followed by high pressure liquid chromatography on a column of RPi) -18 (eluent: acetonitrile / water = 7: 3). At the moment, when no educt can be checked, the reaction mixture is poured into a saturated, aqueous, ice-cold solution.
sodium chloride. The solid product is then separated, washed with water and dried for several hours in the drying cabinet under reduced pressure at 20 ° C. Yield: 62.3 g; H-NMR (270 MHz, in CDC13): d [ppm] = 8.50 (br, lH), 7.80 (dd, lH),
7.60 (dd, lH).
Intermediate 2.3 3-chloro-5-fl-2- (N-methyl-N-triflacetylamino) -nitrobenzene
To a mixture from 16.1 g of 3-chloro-5-fl-2-N-triflacetylamino-nitrobenzene, 11.6 g of potassium carbonate and 100 ml of absolute dimethylformamide are added 12.0 g of methyl iodide. It is then stirred for 18 hours at 20 ° C, after which the reaction mixture is mixed with 500 ml of water. It is then extracted three times with 100 ml of ethyl acetate. The combined organic phases are dried over sodium sulfate and finally concentrated. Yield: 16.3 g; H-NMR (270 MHz, in CDCl 3): d [ppmj = 7.80 (m, 1 H), 7.60 (m, 1 H), 3.40 (s, 3 H). 5 - -
To a solution of 16.3 g of 3-chloro-5-fl-2- (N-methyl-N-tri-flacetylamino) -nitrobenzene in 173 ml of ethanol is added 173 ml of an aqueous, 1-normal solution of sodium hydroxide. It is then stirred for 1 hour, after which the mixture is diluted with 500 ml of water. It is then extracted three times with 80 ml of ethyl acetate. The combined organic phases are washed with water, dried over sodium sulfate and finally concentrated. Yield: 10.1 g; H-NMR (270 MHz, in CDC13): d [ppm] = 7.70 (dd, 1H), 7.35 (dd, 1H), 6.70-6.50 (br, 1H), 3.10 (d, 3H).
!) Reverse phase, on silica gel
Intermediate 2.5 2-amino-6-chloro-4-fl-N-methylaniline
To 10.1 g of 3-chloro-5-fl-2-methylamino-nitrobenzene in 207 ml of absolute ethanol is added 55.94 g of five dihydrate dichloride. The mixture is then heated to 50 ° C and 0.94 g of sodium borohydride in 55 ml of absolute ethanol are added in drops, so that the mixture does not come back stronger than 60 ° C. For further processing, pour over 1 liter of ice water, after which the mixture is adjusted with sodium hydroxide solution to a pH value of 14. It is then extracted three times with 100 ml of tert-butyl methyl ether. . The combined organic phases are washed with water, dried over sodium sulfate and finally concentrated. Yield: 7.5 g; H-NMR (270 MHz, in CDC13): d [ppm] = 6.50 (dd, lH), 6.35 (dd, lH), 3.90-3.60 (br, 3H), 2.65 (s, 3H).
Intermediate 2.6 7-chloro-5-fl-1-methylbenzotriazole
To 7.5 g of 2-amino-6-chloro-4-fl-N-methylaniline in 117 ml of 10% hydrochloric acid is added at 5 ° C a solution of 3.25 g of sodium nitrite in 19 ml of Water. After stirring for one hour at 5 ° C, the reaction mixture is diluted with 200 ml of water. Then the solid proportion is separated, washed with 3x50 ml of water g and dried at 20 ° C in the vacuum drying cabinet. Yield: 7.2 g; iH-NMR (270 MHz, CDC13): d [ppmj = 7.60 (dd, 1H), 7.30 (dd, 1H), 4.55 (s, 3H).
- - - - - - -
To 1.5 g of 7-chloro-5-fl-1-methylbenzotriazole in 28 ml of concentrated sulfuric acid, 0.65 ml of 98% nitric acid are slowly added dropwise at (-20) ° C. It is then stirred for one hour at 0 ° C, after which the mixture is heated to 20 ° C. The mixture is then stirred for 18 hours and the reaction mixture is then poured into 500 ml of ice water. The solid proportion is separated, washed with water and dried at 20 ° C in the vacuum drying cabinet. Yield: 1.66 g; iH-NMR (270 MHz, CDC13): d [ppmj = 7.50 (d, lH), 4.65 (s, 3H).
Intermediate 2.8 4-amino-7-chloro-5-fl-1-methylbenzotriazole
1.66 g of 7-chloro-5-fl-l-methyl-4-nitrobenzotriazole are reduced in analogy to intermediate 2.5 with tin dichloride / sodium boranate. Yield: 1.27 g; iH-NMR (250 MHz, en (CD3) 2SO): d [ppmj = 7.45 (d, lH), 6.25 (br., 2H), 4.45 (s, 3H), 4.30 (q, 2H), 1.35 (t , 3H).
Intermediate 2.9 ethyl 7-chloro-5-fl-1-methyl-lH-benzotriazol-4-yl-carbaminate
To 13 ml of absolute pyridine, 2.28 g of ethyl chloroformate are slowly added dropwise at 0 ° C., after which it is stirred for 15 minutes at this temperature. Then, 1.27 g of 4-amino-7-chloro-5-fl-1-methylbenzotriazole in 20 ml pyridine are added dropwise at 0 ° C. Next, it is stirred, first, another 30 minutes at 0 ° C, then it is heated to 20 ° C and stirred again for 18 hours. Finally, the reaction mixture is poured into 100 ml of 10% hydrochloric acid. It is then extracted three times with 50 ml of tert-butyl methyl ether. The combined organic phases are washed with 100 ml of gewaschen water and then concentrated.
The residue is mixed with 50 ml of diethyl ether. The undissolved proportion is separated and washed with 3x30 ml of diethyl ether. The ethereal facies gathered are concentrated. Yield: 0.37 g; H-NMR (250 MHz, in CDC13): d [ppmj = 7.35 (d, lH), 6.90 (br., LH), 4.55 (S, 3H).
- [-c oro- - uoro-l-met- -tr uorome- - enz m a-zol-4-yl] -l-methyl-6-trifluoromethyl-2,4 (1 H, 3 H) -pyrimidinedione (Comp. 1.5)
2.46 g of 3- [7-chloro-5-fluoro-l-methyl-2-trifluoromethyl-lH-benzi- midazol-4-yl] -6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione are rented in analogy to Example 1 with methyl iodide. Purification of the crude product is carried out by chromatography on sili-cagel (eluent: cyclohexane / ethyl acetate = 2: 1). Yield: 1.4 g; H-NMR (250 MHz, in CDC13): d [ppm] = 7.35 (d, lH), 6.40 (s, lH), 4.30 (S, 3H), 3.55 (s, 3H).
Example 4 3- [7-Chloro-5-fluoro-l-methyl-2-trifluoromethyl-lH-benzimide-zol-4-yl-1-amino-6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione ( Comp 6)
To a mixture from 0.5 g of 3- [7-chloro-5-fluoro-l-methyl-2-trifluoromethyl-lH-benzimidazol-4-yl-6-trifluoromethyl-2,4-trifluoromethyl] (lH, 3H) - pyrimidinedione, 2.35 g of potassium carbonate and 5 ml of ethyl acetate are added 0.25 g of 2,4-dinitro-O-aminophenol. After stirring for 18 hours at 20 ° C, it is diluted with 50 ml of ethyl acetate. The mixture obtained is washed with 3x30 ml of water, dried over sodium sulfate and finally concentrated. The crude product is purified by medium pressure liquid chromatography (MPLC, eluent: cyclohexane / ethyl acetate = 2: 1). Yield: 0.4 g; H-NMR (250 MHz, in CDC13): d [ppm] = 7.35 (d, lH), 6.30 (s, lH), 4.65 (s, 2H), 4.25 (s, 3H).
Example 5 3_ [7-Chloro-5-fluoro-1-methyl-2-trifluoromethyl-1H-benzimide-zol-4-yl-6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (Compound 4)
To 0.82 g of sodium hydride in 50 ml of absolute dimethylformamide are added dropwise at 0 to 5 ° C 4.31 g of ethyl 3-amino-4,4,4-trifluo-robut-2-enoate in 20 g. ml of dimethylformamide. It is then stirred for one hour at the same temperature, after which the mixture is mixed at (-30) ° C with 7-chloro-5-fluoro-4-isocyanato-1-methyl-2-trifluoromethylbenzimidazole (from the product intermediate 5.4) in 40 ml of dimethylformamide. Then, one hour is stirred at (-30) ° C and another hour at 20 ° C.
I am afraid of water. After 10% hydrochloric acid a solid is obtained, which is filtered, washed with water and dried at 20 ° C in the vacuum drying cabinet. After purification by flash cormatofraphy (eluent: cyclohexane / ethyl acetate = 2: 1), 5.08 g of valuable product are obtained.
The valuable product that is still in the filtrate after having separated the solid proportion (2.46 g) is isolated by extracting three times with 200 ml of tere. -butyl methyl ether, washing the combined ether phases, drying over sodium sulfate and concentrating. Total yield: 7.54 g; H-NMR (250 MHz, in CDCl 3): d [ppm] = 7.40 (d, 1 H), 6.30 (S, 1 H), 4.30 (S, 3 H).
Intermediate 5.1 7-chloro-5-fluoro-l-methyl-2-trifluoromethylbenzimidazole
.5 g of 3-chloro-5-fluoro-2- (-methyl-N-trifluoroacetylamino) -nitrobenzene (from intermediate 2.3) are reduced in analogy to intermediate 2.5 with tin dichloride / bora-nato sodium without intermediate isolation, giving the corresponding amino compound, which is then cyclized spontaneously under water separation in the product of value. Yield: 9.32 g; H-NMR (250 MHz, in CDCl 3): d [ppm] = 7.45 (d, 1 H), 7.20 (d, 1 H), 4.25 (s, 3 H).
Intermediate 5.2 7-Chloro-5-fluoro-1-methyl-4-nitro-2-trifluoromethylbenzimidazole
To 9.65 g of 7-chloro-5-fluoro-l-methyl-2-trifluoromethylbenzimidazole in 96.5 ml of acetic anhydride, 46.3 ml of 98% nitric acid are slowly added at 0 ° C. After stirring for one hour at 0 ° C, the mixture is carefully heated to 20 ° C. (When an exothermic reaction is present, then the temperature is maintained by a water bath below 25 ° C.) Then, it is still stirred for two hours at 20 ° C and the reaction mixture is then poured into aqueous solution. , saturated with common salt. The proportion of solid formed is separated, washed with gewaschen water and dried at 20 ° C in the vacuum drying cabinet. Yield: 8.5 g; fí-NMR (400 MHz, in CDC13): d [ppmj = 7.40 (d, lH), 4.35 (s, 3H).
- - - - - or - - - -
8.71 g of 7-chloro-5-fluoro-l-methyl-4-nitro-2-trifluoromethylbenzi-midazole are reduced in analogy to intermediate 2.5 by tin dichloride / sodium boranate. Yield: 6.3 g; ! H-MR (270 MHz, in CDC13): d [ppm] = 7.05 (d, lH), 4.45 (br, 2H), 4.20 (s, 3H).
Intermediate 5.4 7-chloro-5-fluoro-4-isocyanato-l-methyl-2-trifluoromethylbenzimidazole
To 6.3 g of 4-amino-7-chloro-5-fluoro-l-methyl-2-trifluoromethylben-zimidazole in 100 ml of absolute toluene is added 23.32 g of diphosgene. Then, it is heated for 6 hours at reflux temperature. After stirring for a further 18 hours at 20 ° C, the reaction mixture is concentrated. The obtained crude product is transformed without further purification directly giving the final product 1.4.
Example 6 3- [7-Chloro-l, 2-dimethyl-5-fluoro-lH-benzimidazol-4-yl-1-methyl-6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (Compound 8 )
0.33 g of 3- [7-chloro-l, 2-dimethyl-5-fluoro-lH-benzimidazol-4-ylJ-6-trifluoromethyl-2, (1H, 3H) -pyrimidinedione are alkylated in analogy to Example 1 with methyl iodide. Yield: 0.04 g; H-NMR (250 MHz, in CDC13): d [ppmj = 7.10 (d, lH), 6.40 (s, lH), 4.00 (s, 3H), 3.55 (s, 3H), 2.55 (s, 3H) .
Example 7 3- [7-Chloro-l, 2-dimethyl-5-fluoro-lH-benzimidazol-4-yl] -6-trifluo-romethyl-2,4 (1 H, 3 H) -pyrimidinedione (Compound 7)
The 7-chloro-l, 2-dimethyl-5-fluoro-4-isocyanatobenzimidazole of intermediate 7.4 is reacted in analogy to example 5 with ethyl 3-amino-4,4,4-trifluorobut-2-enoate. The crude product is purified by medium pressure liquid chromatography (eluent: ethyl acetate / methanol = 15: 1). Yield: 0.7 g; H-NMR (270 MHz, in CDC13): d [ppmj = 7.15 (d, lH), 6.20 (s, lH), 4.05 (s, 3H), 2.55 (S, 3H).
- -, - e - -
To 6.96 g of 2-amino-6-chloro-4-fluoro-N-methylaniline (from intermediate 2.5) in 4.1 g of acetic anhydride is added 100 ml of 10% hydrochloric acid. Then, it is heated for 4 hours at reflux temperature. After cooling, the mixture is absorbed in ice water. It is then carefully neutralized with an aqueous solution of sodium carbonate. The solid crude product formed is separated, washed with gewaschen water and dried at 20 ° C in the vacuum drying cabinet. Yield: 7.92 g; XH-NMR (270 MHz, in CDC13): O [ppm] = 7.25 (dd, 1H), 6.95 (dd, 1H), 4.00 (s, 3H), 2.55 (s, 3H).
Intermediate 7.2 7-chloro-l, 2-dimethyl-5-fluoro-4-nitrobenzimidazole
To 7.92 g of 7-chloro-l, 2-dimethyl-5-fluorobenzimidazole in 139 ml of concentrated sulfuric acid are added in goras to (-5) up to a maximum of 0 ° C 98% nitric acid, controlling the course of the reaction by high pressure liquid chromatography (HPLC) on a RP-18-Saule column (eluent: acetonitrile / water = 1: 1). At the time, when no eluent can be checked, the reaction mixture is poured into ice water, after which the pH value is regulated by sodium hydroxide solution to 14. The solid is separated, washed with water and at 20 ° C in the vacuum drying cabinet. The regioisomeric nitrogenous compounds formed are separated by flash silica gel chromatography (eluent: ethyl acetate, the product eluting first the desired regioisomer). Yield: 5.6 g; H-NMR (400 MHz, in CDCl 3): d [ppm] = 7.05 (d, 1 H), 4.10 (s, 3 H), 2.65 (s, 3 H).
Intermediate 7.3 4-amino-7-chloro-l, 2-dimethyl-5-fluorobenzimidazole
.6 g of 7-chloro-l, 2-dimethyl-5-fluoro-4-nitrobenzimidazole are re-produced in analogy to intermediate 2.5 by tin dichloride / sodium boranate. The crude product obtained is directly transformed without further purification into intermediate 7.4. Yield: 4.1 g.
- - , - me - - - -
4.1 g of 4-amino-7-chloro-l, 2-dimethyl-5-fluorobenzimidazole was reacted analogously to intermediate 5.4 with diphosgene. The raw product obtained was transformed directly, that is, without further purification, into the final product 1.7.
EXAMPLE 8 10 3- [7-Chloro-2-dimethylamino-5-fluorobenzoxazol-4-yl-1-methyl-6-trifluoromethyl-2, 4- (1 H, 3 H) -pyrimidinedione (Compound 19)
1.0 g of 3- [2-amino-4-chloro-6-fluoro-3-hydroxyphenyl] -l-methyl-6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione are mixed in 100 g.
ml of 1,2-di-chloroethane with 0.5 g of dichloromethylene imonium chloride, after which the glass insert for pressure vessels is introduced and heated in the closed pressure vessel for 5 hours to 120 hours. ° C. The pressure of the pressure vessel itself increases to approx. 5 bar Next, the container is cooled. The clear product solution is washed with dilute aqueous potassium carbonate solution. The organic phase is dried over sodium sulfate and finally concentrated. The crude product is purified by flash chromatography, using a short column (eluent: cyclohexane / tert.-butadylmethyl ether = 8: 2). Yield: 0.5 g; H-NMR (270 MHz, in CDC13): d [ppm] = 6.85 (d, lH), 6.4 (s, lH), 3.6 (s, 3H), 3.25 (s, 6H).
Intermediate 8.1 30 3- [4-chloro-6-fluoro-3-methoxy-2-nitrophenyl] -l-methyl-6-trifluoromethyl-2, 4- (1H, 3H) -pyrimidinedione
To 51.0 g of 3- [4-chloro-6-fluoro-3-methoxyphenyl] -1-methyl-6-trifluoromethyl-2, 4- (1H, 3H) -pyrimidinedione in 1: 1 sulfuric acid Concentrate in droplets under cooling at (-20) ° C, slowly, nitrating acid composed of 20.4 ml of concentrated sulfuric acid and 25.5 ml of 98% nitric acid. When the addition is complete, 30 minutes are stirred at (-20) ° C. The reaction mixture is then introduced under stirring in 1 liter of ice water. The proportion of solid formed is separated, washed with gewaschen water and dried in the vacuum drying cabinet at 20 ° C. Performance:
, 57.0 g; H-NMR (270 MHz, in CDC13): d [ppm] = 7.55 (d, lH), 6.35 (S, 1H), 4.05 (s, 3H), 3.55 (s, 3H). 45 - - - - - - - - - - - - - methyl-2, 4- (1H, 3H) -pyrimidinedione
to 57.0 g of 3- [4-chloro-6-fluoro-3-methoxy-2-nitrophenyl] -l-methyl-6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione in ca. 500 ml of absolute dimethylformamide is added 19.0 g of lithium chloride. Then, stir 3 hours at 80-90 ° C. After cooling, the reaction mixture is mixed with 1 l of water. The 10-value product is extracted with 3x200 ml methyl-tert-butyl ether. dThe ether phase is washed several times with water, then dried and finally concentrated. Yield: 46.1 g; iH-NMR (250 MHz, in CDC13): d [ppmj = 7.65 (d, lH), 6.35 (s, lH), 3.60 (s, 3H). 15 Intermediate 8.3 3- [2-amino-4-chloro-6-fluoro-3-hydroxyphenyl] -l-methyl-6-trifluoromethyl-2, 4- (1H, 3H) -pyrimidinedione
To 46.0 g of 3- [4-chloro-6-fluoro-3-hydroxy-2-nitrophenyl] -1-methyl-6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione in 423 ml of water and 36.8 ml of concentrated hydrochloric acid are added at 65 ° C in portions 34 g of iron powder. Then, it is heated for 3 hours at reflux temperature. After cooling,
The mixture is stirred with 500 ml of ethyl acetate. Filtration on Celite (Manville Corporation) releases the organic phase of the inorganic material remains. The filtrate is dried over sodium sulfate and finally concentrated. Yield: 37.5 g; 30 H-NMR (270 MHz, in CDCl 3): d [ppm] = 6.65 (d, 1 H), 6.40 (s, 1 H), 3.60 (s, 3 H).
Example 9 3- [7-Chloro-5-fluorobenzoxazol-4-yl J-l-methyl-6-trifluoromethyl-2,4- (lH, 3 H) -pyrimidinedione (Comp.12)
To a solution of 0.5 g of 3- [2-amino-4-chloro-6-fluoro-3-hydroxyphenyl] -l-methyl-6-trifluoromethyl-2, 4- (1H, 3H) -pyrimidinedione (from intermediate product 8.3) in 30 ml of absolute methanol is added 40.5 g of trimethyl orthoformate. The solvent and the excessive orthoester are then removed under reduced pressure. The residue is dissolved in ethyl acetate. The organic phase is washed with water, then dried over sodium sulfate and finally concentrated. The crude product is purified by flash chromatography (eluent: cyclohexane / tert-butyl methyl ether = 3: 1). Yield: 0.26 g;
fc3h. ,,. ,.
EXAMPLE 10 5- [7-Chloro-5-fluoro-2-methoxybenzoxazol-4-yl-1-methyl-6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione (Compound 14)
1.0 g of 3- [2-amino-4-chloro-6-fluoro-3-hydroxyphenyl] -l-methyl-6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione (of the product in -10 termedium 8.3), analogue example 9 is reacted with tetramethyl orthoformate. Yield: 0.7 g; l-H-NMR (250 MHZ, in CDCl 3): d [ppm] = 7.10 (d, 1 H), 6.40 (S, 1 H), 4.20 (s, 3 H), 3.60 (s, 3 H).
In Table 2 below other 3- (benzazol-4-yl) pyrimidinedione derivatives of the formula I are indicated in addition to those described above, which were prepared or can be prepared analogously:
twenty
40
45 Table 2
H; R5 = Cl.}.
00
Application examples
The herbicidal action of the 3- (benzazol-4-yl) pyrimidinedione I derivatives can be demonstrated by the following greenhouse tests:
Plastic pots filled with clay sand with approx. 3.0% humus as substrate. The seeds of the test plants are sown separately according to the species.
In the treatment before the emergency, actibas substances suspended or emulsified in water are applied directly after sowing by means of fine distribution nozzles. The containers are irrigated slightly to encourage germination and growth, and then the pots are covered with transparent plastic bags until the plants have taken root. With this covering a uniform germination of the test plants is reached, as this is not counteracted by the active substances.
For the post-emergence treatment, the test pan is grown until it has reached a growth height of 3 to 15, depending on its growth pattern, and then treated with the active substances suspended or emulsified in water. For this purpose, the test plants are sown directly in the same containers in which they are grown, or they are sown in separate germination containers and the seedlings are planted some days before the treatment in the test vessels. The amount of application in the treatments after the emergency amount to 15.6 or 7.8 g / ha of s.a.
The plants were maintained according to their species at temperatures of 10 to 25 ° C or 20 to 35 ° C. The trial period amounted to 2 to 4 weeks. During this time, the plants were taken care of and their reaction to the different treatments was evaluated.
The assessment is based on a scale of 0 to 100, where 100 means no emergence or total destruction of at least the parts of the plants surfaced, and 0 means no damage or normal growth.
The plants used in the trials in the greenhouse belong to the following species:
Applied in quantities of 15.6 and 7.8 g / ha of s.a., compound No. 18 presents a very good herbicidal action in postemergence treatments against the weeds indicated above.
Claims (4)
- Derivatives of 3- (benzazol-4-yl) pyrimidinedione of the formula I in which the variables have the following meanings: X oxygen or sulfur; Ri hydrogen, amino, C? -C6-alkyl or C? -C6-halogenoalkyl; R 2 hydrogen, halogen, C 6 -C alkyl, C 6 -Chaloalkyl, C 6 -C alkylthio, C 6 -C alkylsulfinyl or C 6 -C 6 alkylsulphonyl; R3 hydrogen, halogen or C? -C6 alkyl; R4 hydrogen or halogen; R5 cyano, halogen, C? -C6-alkyl, C? -C6-haloalkyl, C? -C6-alkoxy or C? -C6-halogenoalkoxy; = Y- one group = N-N (R6) -, = C (ZR7) -N (R6) -, = C (ZR7) -0- or = C (ZR7) -S-; R6 C? -Cg-alkyl, C? -C4-haloalkyl, C3-Cg-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C? -Cg-alkylsulfonyl, (C? -Cg-alkyl) carbonyl, (C? -C6-haloalkyl) carbonyl, (C? -C6-alkyl) thiocarbonyl, (C? -C6-alkoxy) carbonyl, (C? -Cg-alkoxy) thiocarbonyl or C? -Cg-alkyl, which may be substituted by cyano, C? -C6-alkoxy, C-C6-alkylthio, (C? -C6-alkoxy) carbonyl, (C? -C6-alkylamino) carbonyl, Di (C? -C6-alkyl) aminocarbonyl or (Cx) -Cß-alkyl) carbonyloxy; Z a chemical bond, oxygen, sulfur, -S (O) -, -S (0) 2-, -NH- or -N (R8) -; R7 and R8 each independently of the other, qu o, c ano-? -4-a,? - - -? - 4-, C? -C4-halogenoalkoxy-C? -C4-alkyl, C3-C4-alkenyloxy- C? -C4-alkyl, C3-C4-alkynyloxy-C? -C4-alkyl, C3-C8-cycloalkoxy-C? -C4-alkyl, amino-C? -C4-alkyl, C? -C4-alkylamino -C? -C -alkyl, di (C? -C4-alkyl) amino-C? -C4-alkyl, C? -C4-alkylthio-C? -C4-alkyl, C? -C4-haloalkylthio-C? C4-alkyl, C3-C4-alkenylthio-C? -C4-alkyl, C3-C4-alkynylthio-C? -C4-alkyl, C? -C4-alkylsulfinyl-C? -C4-alkyl, C? -C4-halogenoalkylsulfinyl -C? -C4-alkyl, C3-C4-alkenylsulfinyl-C? -C4-alkyl, C3-C4-alkynylsulfinyl-C? -C4-alkyl, C? -C4-alkylsulfonyl-C? -C4-alkyl, C? -C4-halogenoalkylsulfonyl-C? -C4-alkyl, C3-C4-alkenylsulfonyl-C? -C4-alkyl, C3-C4-alkynylsulfonyl-C? -C4-alkyl, C3-Cg-alkenyl, cyano- C3-Cg-alkenyl, C3-C6-haloalkenyl, C3-Cg-alkynyl, cyano-C3-Cg-al-quinyl, C3-Cg-haloalkynyl, hydroxycarbonyl-C? -C4-alkyl, (C? -C4-alkoxy) carbonyl-C? -C4-alkyl, (C? -C4-alkylthio) carbonyl-C? C4-alkyl, aminocarbonyl-C? -C -alkyl, (C? -C4-alkylamino) carbonyl-C? -C4-alkyl, di (C? -C4-alkyl) aminocarbonyl-C? -C4-alkyl, di ( C? -C4-al-quil) -phosphonyl-C? -C4-alkyl, C3-C8-cycloalkyl, C3-C8-C-C4-cycloalkyl-alkyl, phenyl, phenyl-C? -C4-alkyl, heterocyclyl to 7 members or heterocyclyl-C? -C4-alkyl, each heterocyclyl ring can contain a carbonyl or thiocarbonyl ring member, and each cycloalkyl, phenyl and heterocyclyl ring can be unsubstituted or carry from one to four substituents, each selected from the a group comprising cyano, nitro, amino, hydroxy, carboxy, halogen, C? -C4-alkyl, C? -C4-haloalkyl, C? -C4-alkoxy, C? -C4-halogenoalkoxy, C? -C4-alkylthio, C? -C4-haloalkylthio, C? -C4-alkylsulfonyl, C? -C4-haloalkylsulfo-nyl, (C? -C4-alkoxy) carbonyl, (C? -C4-alkyl) carbonyl, (C? -C4) -halogenalkyl) carbonyl, (C? -C4-alkyl) carbonyloxy, (C? -C4-haloalkyl) carbonyloxy and di (C? -C4-al-quil) amino, or, whenever Z means a chemical bond, R7 can mean, if desired, also hydrogen, hydroxy, cyano, mercapto, amino, halogen, -CH (OH) -CH2-R9 -CH (halogen) -CH2-R9 , -CH-CH (halogen) -R9, -CH = CH-R9 O -CH = C (halogen) -R9, where? -4-,,? -4-lamino) carbonyl or di (C? -C4) -alkyl) aminocarbonyl, or R7 and R8 together form a chain of 1,3-propylene, tetramethylene, pentamethylene or ethyleneoxyethylene, which may in each case be unsubstituted or carry one to four C? -C4 alkyl groups or one or two groups ( C? -C -alkoxycarbonyl; as well as the salts useful in the agriculture of the compounds i. 3- (Benzazol-4-yl) pyrimidinedione derivatives of the formula I according to claim 1, wherein X is oxygen, R 1 is hydrogen, amino or C? -Cg-alkyl, R 2 is hydrogen, halogen, C? -C6 -alkyl, C? -Cg-haloalkyl or C? -Cg-alkylsulfonyl, R3 is hydrogen, R4 is hydrogen, fluorine or chlorine, R5 is cyano or halogen and R6 is C? -Cg-alkyl, C3-Cg-alkynyl, C? -Cg-alkylsulphonyl or (C? -Cg-alkoxy) carbonyl. Use of the 3- (benzazol-4-yl) pyrimidinedione derivatives I and their salts useful in agriculture according to claim 1 as herbicides. Herbicidal products containing a herbicidal active amount of at least one 3- (benzazol-4-yl) pyrimidinedione derivative of the formula I or a salt of I according to claim 1 and at least one support liquid and / or solid, as well as, if desired, at least, a tenso-active substance. Process for obtaining herbicidal products, characterized in that a herbicidal active quantity of at least one derivative of 3- (benzazol-4-yl) pyrimidinedione of the formula I or a salt of I according to claim 1 is mixed, and at least one liquid / solid support, as well as, if desired, at least one surfactant substance. Procedure to control the. growth of indeterminate plants, characterized in that an active herbicidal amount of at least one derivative of 3- (benzene) is made to act on the plants, their living space or the seeds. SUMMARY OF THE INVENTION Derivatives of 3- (benzazole) -4-yl) pyrimidinedione I and its salts, where X O, S; R1 H, NH2 / C? -Cg-alkyl, C? -Cg-haloalkyl; R2 H, halogen, C? -Cg-alkyl, C? -Cg-haloalkyl, C? -Cg-alkylthio, C? -Cg-alkylsulfinyl, C? -C6-alkylsulphonyl; R3 H, halogen, C? -Cg-alkyl; R4 H, halogen; R5 CN, halogen, C6-C6-alkyl, C6-C6-haloalkyl, C6-C6-alkoxy, C6-C6-haloalkoxy; _? _ = one group = N-N (R6) -, = C (ZR7) -N (R6) -, = C (ZR7) -0-, = C (ZR7) -S-; R6 = _C? -Cg-alkyl, C? -C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-Cg-alkynyl, C? -Cg-alkyl-S02, C? -C6 -alkyl-CO, C? -C6-haloalkyl-CO, C? -C6 -alkyl-CS, C? -C6-alkoxy-CO, C? -C6-alkoxy-CS or Cx-Cg-optionally substituted alkyl; chemical bond, 0, S, -S (0) -, -S0 -, -NH-, -N (R8) -; R7, R8 = C? -Cg-alkyl, C? -Cg-haloalkyl, hydroxy-C? -C -alkyl, cyano-C? -C4-alkyl, C? -C4-alkoxy-C-C4-alkyl , C? -C4-haloalkoxy-C? -C -alkyl, C3-C4-alkenyloxy-C? -C4-alkyl, C3-C4-alkynyloxy-C? -C4-alkyl, a re vn cac n. Arylureas of the formula III wherein L2 means C? -C4-alkyl or phenyl and Ri-R5 as well as Y have the meanings indicated in claim 1. Arylamilides of the formula IV wherein L2 means C? -C4-alkyl or phenyl and Ri-R5 as well as Y have the meanings indicated in claim 1.
- 2-Aminophenols, substituted -thiophenols and substituted -anilines of the formula V wherein the variables X and R-R6 have the meanings indicated in claim 1. - - -? - 4-,? - - - C -C -alkyl, C? -C4-alkylthio-C? -C -alkyl, C? -C -haloalkylthio-C? -C4 -alkyl, C
- 3-C
- 4- alkenylthio-C?-C4-alkyl, C3-C4-alkynylthio-C?-C4-alkyl, C?-C4-alkylsulfinyl-C?-C4-alkyl, C?-C4-halogenoalkylsulfinyl-C?-C4- alkyl, C3-C4-alkenylsulfinyl-C? -C4-alkyl, C3-C4-alkynylsulfinyl-C? -C4-alkyl, C? -C4-alkylsulfonyl-C? -C4-alkyl, C? -C4-haloalkylsulphonyl -C? -C4-alkyl, C-C4-alkenylsulfonyl-C? -C-alkyl, C3-C4-alkynylsulfonyl-C? -C -alkyl, C3-Cg-alkenyl, cyano-C3-Cg-alkenyl, C3- Cg-halogen-alkenyl, C3-Cg-alkynyl, cyano-C3-Cg-alkynyl, C3-C6-haloalkynyl, HO-CO-C? -C4-alkyl, (C? -C4-alkoxy) C0-C C4-alkyl, (C? -C4-alkyl) CS-C? -C4-alkyl, H2N-CO-C? -C4-alkyl ?, C? -C4-alkyl-NHC0-C? -C4-alkyl , di (C? -C4-alkyl) NCO-C? -C4-alkyl, di (C? -C4-alkyl) fos-fonyl-C? -C4-alkyl, C3-C8-optionally substituted cycloalkyl, C3-C8 -cycloalkyl-C? -C-alkyl, phenyl, phenyl-C? -C4-alkyl, heterocyclyl or heterocyclic il-C? -C4-alkyl of 3 to 7 members, each heterocyclyl ring being able to contain an annular member of CO or CS, or, if Z = chemical bond, then R7 also means H, OH, CN, SH, NH2, halogen, -CH (OH) -CH2-R9, -CH (halogen) -CH2-R9, -CH2-CH (halogen) ) -R9, -CH = CH-R9 or -CH = C (halogen) -R9, where R9 = COOH, (C? -C4-alkoxy) carbonyl, (C? -C-alkylthio) carbonyl, C0NH2, C? -C4-alkyl-NHCO or di (C? -C4-alkyl) NCO, or R7 + R8 = a chain of optionally substituted 1,3-propylene, tetramethylene, penta-methylene or ethyleneoxyethylene.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19755926.3 | 1997-12-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
MXPA00005040A true MXPA00005040A (en) | 2001-07-03 |
Family
ID=
Similar Documents
Publication | Publication Date | Title |
---|---|---|
SK286069B6 (en) | 3-Heterocyclyl-substituted benzoyl derivatives, process for their preparation, compositions comprising them and their use | |
EP1047693A1 (en) | Herbicides 3-(benzazol-4-yl)pyrimidine-dione-derivatives | |
WO2000028822A2 (en) | Herbicidal 3-(benzo(ox/thi)azol-7-yl)-1h-pyrimidine-2,4-diones | |
EP0944623B1 (en) | Substituted pyrazole-3-yl benzazoles | |
EP1200428B1 (en) | Substituted benzoxazoles | |
EP1076660B1 (en) | Substituted (4-brompyrazole-3-yl)benzazoles | |
JP2000507250A (en) | Substituted 1-methyl-3-benzyluracil | |
NZ521090A (en) | 7-(pyrazole-3-yl) benzoxazole derivatives, method for their production, use as herbicides | |
EP0915853B1 (en) | Substituted 3-phenyl pyrazoles | |
MXPA00005040A (en) | Herbicides 3-(benzazol-4-yl)pyrimidine-dione-derivatives | |
WO1999006394A1 (en) | Substituted 2-(benzoaryl)pyridines | |
WO1998012182A1 (en) | 1-sulfonyl-3-phenylpyrazoles and their use as herbicides and for desiccating or defoliating plants | |
EP1003741A1 (en) | Substituted herbicide tetrazolinonecarboxylic acid amides | |
WO1997015559A1 (en) | Substituted 4,5-di(trifluoromethyl)pyrazoles and their use as herbicides and for desiccating/defoliating plants | |
DE19645313A1 (en) | Substituted 3-benzylpyrazoles | |
WO2001087863A1 (en) | 3-arylisothiazoles and their use as herbicides | |
MXPA99005530A (en) | Substituted pyrazole-3-yl benzazoles | |
CZ20002105A3 (en) | Herbicidal 3-(benzazol-4-yl)pyrimidinedione derivatives, their use, herbicidal composition, process of its preparation and intermediates | |
MXPA01004865A (en) | 3-&lcub;BENZ(OX/THI)AZOL-7-YL&rcub;-1H-PYRIMIDINE-2,4-DIONES | |
CZ214599A3 (en) | Substituted pyrazol-3-yl-benzazoles | |
WO2001019820A1 (en) | Substituted pyrazol-3-ylbenzoxazinones |