MXPA99005164A - Thienylsulfonylamino(thio)carbonyl compounds - Google Patents
Thienylsulfonylamino(thio)carbonyl compoundsInfo
- Publication number
- MXPA99005164A MXPA99005164A MXPA/A/1999/005164A MX9905164A MXPA99005164A MX PA99005164 A MXPA99005164 A MX PA99005164A MX 9905164 A MX9905164 A MX 9905164A MX PA99005164 A MXPA99005164 A MX PA99005164A
- Authority
- MX
- Mexico
- Prior art keywords
- atoms
- sarbono
- alkyl
- given
- saso
- Prior art date
Links
- 125000000446 sulfanediyl group Chemical group *S* 0.000 title claims abstract description 8
- 125000004432 carbon atoms Chemical group C* 0.000 claims abstract description 107
- 150000001875 compounds Chemical class 0.000 claims abstract description 53
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 42
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 36
- 150000002367 halogens Chemical class 0.000 claims abstract description 36
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 35
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 34
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 16
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
- 239000001301 oxygen Substances 0.000 claims abstract description 15
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000011593 sulfur Substances 0.000 claims abstract description 15
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 239000011780 sodium chloride Substances 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- -1 (thio) carbonyl Chemical group 0.000 claims description 103
- 125000004429 atoms Chemical group 0.000 claims description 75
- 239000000460 chlorine Chemical group 0.000 claims description 49
- 229910052801 chlorine Inorganic materials 0.000 claims description 49
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 49
- 239000011737 fluorine Substances 0.000 claims description 49
- 229910052731 fluorine Inorganic materials 0.000 claims description 49
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 43
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 34
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 34
- 241000196324 Embryophyta Species 0.000 claims description 21
- 239000003085 diluting agent Substances 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 9
- YBBRCQOCSYXUOC-UHFFFAOYSA-N Sulfuryl chloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- WQJONRMBVKFKOB-UHFFFAOYSA-N cyanatosulfanyl cyanate Chemical class N#COSOC#N WQJONRMBVKFKOB-UHFFFAOYSA-N 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 150000003456 sulfonamides Chemical class 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 229940093912 Gynecological Sulfonamides Drugs 0.000 claims description 4
- 125000005108 alkenylthio group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000005109 alkynylthio group Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 229940079867 intestinal antiinfectives Sulfonamides Drugs 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229940005938 ophthalmologic antiinfectives Sulfonamides Drugs 0.000 claims description 4
- 229940026752 topical Sulfonamides Drugs 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 2
- 125000005210 alkyl ammonium group Chemical class 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000006319 alkynyl amino group Chemical group 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000004660 phenylalkylthio group Chemical group 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 241001243925 Sia Species 0.000 claims 2
- 125000005324 aryloxy alkyloxy group Chemical group 0.000 claims 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 159000000003 magnesium salts Chemical class 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 159000000001 potassium salts Chemical class 0.000 claims 1
- 239000002002 slurry Substances 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 230000002363 herbicidal Effects 0.000 abstract description 7
- 239000004009 herbicide Substances 0.000 abstract description 6
- 125000006193 alkinyl group Chemical group 0.000 abstract 2
- 239000000047 product Substances 0.000 description 29
- 238000002360 preparation method Methods 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000007858 starting material Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- CPPKAGUPTKIMNP-UHFFFAOYSA-N Cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 description 9
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- ZOAMZFNAPHWBEN-UHFFFAOYSA-N 2-$l^{1}-oxidanylpropane Chemical group CC(C)[O] ZOAMZFNAPHWBEN-UHFFFAOYSA-N 0.000 description 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 7
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 7
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 235000005822 corn Nutrition 0.000 description 6
- 235000005824 corn Nutrition 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 240000008042 Zea mays Species 0.000 description 5
- 239000000370 acceptor Substances 0.000 description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 5
- 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 4
- 241001049165 Caria Species 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 241001310793 Podium Species 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 235000021307 wheat Nutrition 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N DABCO Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
- 235000005775 Setaria Nutrition 0.000 description 3
- 241000232088 Setaria <nematode> Species 0.000 description 3
- 241000209149 Zea Species 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- QRVPHJIVUWTJSU-UHFFFAOYSA-N but-1-en-2-ylazanide Chemical group [CH2+]CC([NH-])=C QRVPHJIVUWTJSU-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 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 3
- 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 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000012439 solid excipient Substances 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- HNJQTWWFDBLRDL-UHFFFAOYSA-N t-butylamino Chemical group [CH2]C([CH2+])([CH2-])[N-] HNJQTWWFDBLRDL-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-Diazabicyclo(4.3.0)non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 2
- WICSALYSMRRIOV-UHFFFAOYSA-N 2,4-dimethylthiophene-3-sulfonamide Chemical compound CC1=CSC(C)=C1S(N)(=O)=O WICSALYSMRRIOV-UHFFFAOYSA-N 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M Copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L Copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- YQVMVCCFZCMYQB-UHFFFAOYSA-N Flamprop Chemical compound C=1C=C(F)C(Cl)=CC=1N(C(C)C(O)=O)C(=O)C1=CC=CC=C1 YQVMVCCFZCMYQB-UHFFFAOYSA-N 0.000 description 2
- 239000005562 Glyphosate Substances 0.000 description 2
- 241000207783 Ipomoea Species 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N Methyl acetate Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- 241000209117 Panicum Species 0.000 description 2
- 241000207763 Solanum Species 0.000 description 2
- 235000002634 Solanum Nutrition 0.000 description 2
- 240000006394 Sorghum bicolor Species 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 235000006442 blackseeded proso millet Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 235000006443 broomcorn panic Nutrition 0.000 description 2
- FQFTUKDNONXKLN-UHFFFAOYSA-N but-1-yn-1-olate Chemical group [CH2+]CC#C[O-] FQFTUKDNONXKLN-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 235000008216 herbs Nutrition 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- AWIJRPNMLHPLNC-UHFFFAOYSA-N methanethioic S-acid Chemical class SC=O AWIJRPNMLHPLNC-UHFFFAOYSA-N 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000003389 potentiating Effects 0.000 description 2
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- 239000001007 phthalocyanine dye Substances 0.000 description 1
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- 229920000642 polymer Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000001184 potassium carbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002035 prolonged Effects 0.000 description 1
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- OYJMHAFVOZPIOY-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1 OYJMHAFVOZPIOY-UHFFFAOYSA-N 0.000 description 1
- FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 description 1
- 125000006324 propenyl amino group Chemical group 0.000 description 1
- 125000006320 propynyl amino group Chemical group 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective Effects 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
- 229910052904 quartz Inorganic materials 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 239000001187 sodium carbonate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 229910001929 titanium oxide Inorganic materials 0.000 description 1
- 125000005881 triazolinyl group Chemical group 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Abstract
This invention concerns new thienylsufonylamino(thio)carbonyl compounds of formula (I) in which Q stands for oxygen of sulfur, R1 stands for cyano, halogen or alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy, optionally substituted in each case by cyno, halogen or C1-C14 alkoxy and having up to 6 carbon atoms, R2 stands for cyano, halogen or alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy, optionally substituted in each case by cyano, halogen or C1-C14 alkoxy and having up to 6 carbon atoms, and R3 stands for in each case optionally substituted heterocyclyle with 5 ring members of which at least one stands for oxygen, sulfur or nitrogen and one to three more stand for nitrogen. The invention also relates to salts of compounds of formula (I), processes, and new intermediate products for producing these new compounds, and their use as herbicides.
Description
- i - T-EE COMPOUNDS ILSULFOJILAMINO (UNCLE) CARBO IL / 3 Field of the invention. The invention relates to novel thienylsulfo-nylamino (thio) carbonyl compounds, various processes and new intermediates for their preparation as well as their use as herbicides. Description of the prior art. It is already known that certain sulfonylaminocarbo-nyl-co-acids exhibit herbicidal properties (cf. EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266, DE 4029753). However, the effect of these compounds is not satisfactory on all occasions. Detailed description of the invention. The new thienylsulfo-nylamino (thio) carbonyl compounds of the general formula (I) have now been found,
wherein Q means oxygen or sulfur, R1 means cyano, halogen or means alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy or alkynyloxy with
REF .: 30262- respectively up to 6 carbon atoms, substituted respectively by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, R2 means cyano, halogen or means alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy or alkynyloxy, with respectively up to 6 carbon atoms substituted, where appropriate, by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, and
R3 means heterocyclyl, respectively substituted if appropriate, with 5 members in the ring, meaning at least one of them, oxygen, sulfur or nitrogen and can mean 1 to 3 more nitrogen, as well as the salts of the compounds of the formula (I) ). The new thienylsulfonylamino (-thio) carbonyl-compounds of the general formula (I) are obtained, if
(a) sulphonamides of the general formula (II) are reacted
wherein R1 and R2 have the meaning indicated above, with (thio) carboxylic acid derivatives of the general formula (III) .X. (H1) Z '"in which Q and R3 have the meaning indicated above and Z means halogen, alkoxy, aryloxy or arylalkoxy, optionally in the presence of an acid acceptor and, if appropriate, in the presence of a diluent, or if (b) sulfonyliso (thio) cyanates of the general formula (IV) are reacted
wherein Q, R1 and R2 have the meaning indicated above, with heterocycles of the general formula (V) H-R3"1 (V) wherein > 3-l stands for heterocyclyl, optionally substituted, with 5 members in the ring, meaning at least one of them> NH, if appropriate in the presence of an auxiliary agent of the reaction and optionally in the presence of a diluent, or if (c) sulphonyl chlorides are reacted from the - general mule (VI)
wherein R1 and R2 have the meaning indicated above, with heterocycles of the general formula (V) H-R3"1 (V) in which R3-1 has the meaning previously indicated in (b), with (thio) cyanates of the general formula (VII) QCN (VII) in which Q has the meaning indicated above and M means a metallic equivalent, if appropriate in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent, or if (d) sulphonyl chlorides of the general formula (VI) are reacted
wherein R1 and R2 have the meaning indicated above, with (thio) carboxylic acid amides of the general formula (VIII)
wherein Q and R3 have the meaning indicated in the case of formula (I), if appropriate in the presence of an acid acceptor and, if appropriate, in the presence of a diluent, or if (e) they are reacted Sulfonylamino (thio) carbonyl-compounds of the general formula (IX)
wherein Q, R1 and R2 have the meaning indicated above and Z means halogen, alkoxy, aryloxy or arylalkoxy, with heterocycles of the general formula (V) H-R3"1 (V) in which R3_1 has the meaning indicated above in (b), if appropriate, in the presence of an acid acceptor and, if appropriate, in the presence of a diluent, and, if appropriate, the compounds obtained according to the procedures (a), (b), (c), (d) and (e) are transformed into sails according to usual methods. The processes (b), (c) and (e) are naturally suitable only for obtaining those compounds of the formula (I) in which R3 means R3-1. The novel thienylsulfonylamino (thio) carbonyl compounds of the general formula (I) are characterized by a potent herbicidal activity. The subject of the invention are preferably compounds of the formula (I), in which Q is oxygen or sulfur, R 1 is cyano, halogen, means alkyl having 1 to 4 carbon atoms, optionally substituted by cyano, halogen, or by alkoxy with 1 to 4 carbon atoms, means alkenyl with 2 to 4 carbon atoms or alkynyl with 2 to 4 carbon atoms substituted, if appropriate, by cyano or by halogen, means alkoxy with 1 to 4 carbon atoms optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, or means alkenyloxy with 2 to 4 carbon atoms or alkynyloxy with 3 to 4 carbon atoms substituted, respectively, by cyano or Halogen, R 2 means cyano, halogen, means alkyl having 1 to 4 carbon atoms, optionally substituted by cyano, by halogen, or by alkoxy with 1 to 4 carbon atoms, means alkenyl with 2 to 4 carbon atoms or alkynyl with 2 to 4 carbon atoms substituted, where appropriate, by cyano or by halogen, means alkoxy with 1 to 4 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, or means alkenyloxy with 2 to 4 carbon atoms; carbon or alkynyloxy atoms with 3 to 4 carbon atoms substituted, where appropriate, by cyano or halogen, and R 3 means heterocyclyl, respectively substituted, if appropriate, of the following formulas
where Q1, Q2 and Q3 respectively mean oxygen or sulfur, and R4 is hydrogen, hydroxy, amino, cyano, means alkylidenamino having 2 to 10 carbon atoms, meaning alkyl having 1 to 6 carbon atoms, optionally substituted with fluorine , by chlorine, by bromine, by cyano, by alkoxy with 1 to 4 carbon atoms, by alkylcarbonyl with 1 to 4 carbon atoms or by alkoxycarbonyl with 1 to 4 carbon atoms, means alkenyl with 2 to 6 carbon or alkynyl atoms with 2 to 6 carbon atoms substituted, if appropriate, by fluorine, chlorine and / or bromine, means alkoxy with 6 carbon atoms, alkylamino with 1 to 6 carbon atoms or alkyl-carbonylamino with 1 to 6 carbon atoms substituted respectively by fluorine, chlorine, bromine, cyano, alkoxy with 1 to 4 carbon atoms or alkoxycarbonyl with 1 to 4 carbon atoms means alkenyloxy with 3 to 6 carbon atoms, means di- (a alkyl with 1 to 4 carbon atoms) -amino, means cycloalkyl with 3 to 6 carbon atoms, cycloalkylamino with 3 to 6 carbon atoms or cycloalkyl with 3 to 6 carbon atoms-alkyl with 1 to 4 carbon atoms substituted respectively optionally fluorine, chlorine, bromine, cyano and / or alkyl having 1 to 4 carbon atoms, or phenyl or phenyl-alkylaryl having 1 to 4 carbon atoms, respectively substituted, if appropriate, by fluorine , by chlorine, by bromine, by cyano, by nitro, by alkyl with 1 to 4 carbon atoms, by trifluoromethyl and / or by alkoxy with 1 to 4 carbon atoms, ignites hydrogen, hydroxy, mercapto, amino, cyano, fluorine , chlorine, bromine, iodine, means alkyl having 1 to 6 carbon atoms, optionally substituted by fluorine by chlorine, by bromine, by cyano, by alkoxy with 1 to 4 carbon atoms, by alkyl-carbonyl with 1 to 4 atoms of carbon or by alkoxy-carbonyl with 1 to 4 carbon atoms, means alkenyl with 2 to 6 carbon or alkynyl atoms having 2 to 6 carbon atoms substituted, if appropriate, by fluorine, chlorine and / or bromine, means alkoxy having 1 to 6 carbon atoms, alkylthio having 1 to 6 carbon atoms, alkylamino with 1 to 6 carbon atoms or alkylcarbonylamino with 1 to 6 carbon atoms, optionally substituted, if appropriate, by fluorine, chlorine, cyano, alkoxy with 1 to 4 carbon atoms, or by alkoxy carbonyl with 1 to 4 carbon atoms means alkenyloxy with 3 to 6 carbon atoms, alkynyloxy with 3 to 6 carbon atoms, alkenylthio with 3 to 6 carbon atoms, alkynylthio with 3 to 6 carbon atoms, alkenylamino with 3 6 carbon atoms or alkynylamino with 3 to 6 carbon atoms, means di- (alkyl having 1 to 4 carbon atoms) -amino, means aziridino, pyrrolidino, piperidino or morpholino, respectively substituted, if appropriate, by methyl and / or ethyl , means cycloalkyl with 3 to 7 carbon atoms, C5-C6alkalkenyl, cycloalkyloxy with 3 to 6 carbon atoms, cycloalkylthio with 3 to 6 carbon atoms, cycloalkylane with 3 to 6 carbon atoms, cycloalkyl with 3 to 6 carbon atoms- alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms-alkoxy with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms-alkylthio with 1 to 4 carbon atoms or cycloalkyl with 3 carbon atoms; at 6 carbon atoms-alkylamino having 1 to 4 carbon atoms, optionally substituted, respectively, by fluorine, chlorine, bromine, cyano and / or alkyl having 1 to 4 carbon atoms, or means phenyl, phenyl- alkyl with 1 to 4 carbon atoms, phenoxy, phenyl-alkoxy with 1 to 4 carbon atoms, phenylthio, phenyl-alkylthio with 1 to 4 carbon atoms, phenylamino or phenyl-alkylamino with 1 to 4 carbon atoms substituted respectively, where appropriate, fluorine, chlorine, bromine, cyano, nitro, alkyl with 1 to 4 atoms of carbon, by trifluoromethyl, by alkoxy with 1 to 4 carbon atoms and / or by alkoxy-carbonyl with 1 to 4 carbon atoms, and R5 together, mean alkanediyl, if any branched, with 3 to 11 carbon atoms, further R6, R7 and R8 are the same or different and mean hydrogen, cyano, fluorine, chlorine, bromine, or mean alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylsulfinyl or alkylsulfonyl with respectively up to 6 carbon atoms, each optionally substituted by fluorine, chlorine, bromine or alkoxy with 1 to 4 carbon atoms - or not meaning cycloalkyl with 3 to 6 carbon atoms, optionally substituted by cyano, fluorine, chlorine, bromine or alkyl with 1 to 4 carbon atoms. The object of the invention is also preferably sodium, potassium, magnesium, calcium, ammonium, alkyl-ammonium salts with 1 to 4 carbon atoms, di- (alkyl with 1 to 4 carbon atoms). carbon) -ammonium, tri- (C1-C4 alkyl) -ammonium, tetra- (C1-C4 alkyl) -ammonium, tri- (C1-C4 alkyl) sulfonium, cycloalkyl ammonium with 5 or 6 carbon atoms and di- (C 1 -C 2 alkyl) -benzyl ammonium of the compounds of the formula (I), wherein Q, R 1, R 2 and R3 have the previously given meaning preferentially.
The subject of the invention are especially compounds of the formula (I), in which Q is oxygen or sulfur, R 1 is cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n- , i- or s-butyl substituted, where appropriate, by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, means propenyl, butenyl, propinyl or butynyl substituted, where appropriate, by cyano, by fluorine or by chlorine, respectively methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy substituted, where appropriate, by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, or means propenyloxy, butenyloxy, propynyloxy or butynyloxy substituted, where appropriate, by cyano, fluorine or chlorine, R2 means cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl substituted respectively in case given by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, means propenyl, butenyl, propinyl or bu tinyl substituted, where appropriate, by cyano, fluorine or chlorine, means methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy substituted, where appropriate, by cyano, by fluorine, by chloro, methoxy or ethoxy, or means propenyloxy, butenyloxy, pro-phenyloxy or butynyloxy substituted, where appropriate, by cyano, fluorine or chlorine, and R3 means substituted heterocyclyl, respectively, of the following formulas
where Q1, Q2 and Q3 respectively mean oxygen or sulfur, and R4 is hydrogen, hydroxy, amino, means methyl ethyl, n- or i-propyl, n-, i-, s- or t-butyl substituted, respectively, by fluorine, chlorine, cyano, methoxy or ethoxy, means propenyl, butenyl, propynyl or butynyl substituted, if appropriate, by fluorine, chlorine or bromine, means methoxy, ethoxy, n- or i-propoxy, n - i-, s- or t-butoxy, methylamino, ethylamino, n- or i- propylamino, n-, i-, s- or t-butylamino substituted, where appropriate, by fluorine, by chlorine, by cyano, by methoxy or by ethoxy, means propenyloxy, or butenyloxy, means dimethylamino or diethylamino, means cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclo-pentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl substituted respectively where appropriate by fluorine, by chlorine, by methyl or and / or by ethyl, or means phenol or benzyl substituted, where appropriate, by fluorine, chlorine, methyl, trifluoromethyl and / or methoxy, hydrogen, hydroxy, mercapto, amino, fluorine, chlorine, bromine, means methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl substituted respectively by fluorine, by chlorine, by cyano, by methoxy or by ethoxy, means ethenyl, propenyl, butenyl , propynyl or butynyl substituted, where appropriate, by fluorine, chlorine or bromine, means methoxy, ethoxy, n- or i-propoxy, n-, i- s- or t-butoxy, methylthio, ethylthio, n- or -propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino respectively substituted, if appropriate by fluorine, by chlorine, by cyano, methoxy or ethoxy, means propenyloxy, butenyloxy propynyloxy, butynyloxy, propenylthio, propadienylthio, butenylthio, propynylthio, butynylthio, propenylamino, butenylamino, propylamino or butyne. ilamino, means dimethylamino, diethylamino or dipropylamino, means cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylthiamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino substituted, where appropriate, by fluorine, by chlorine, by methyl and / or ethyl, or by phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino substituted, where appropriate, by fluorine, chlorine, methyl, trifluoromethyl, methoxy and / or methoxycarbonyl, or R4 and R5 together mean alkanediyl, optionally branched, with 3 to 11 carbon atoms , further R6, R7 and R8 are the same or different and denote hydrogen, cyano, fluorine, chlorine, bromine, or mean methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , propenyl, butenyl, propynyl, butenyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, propenyloxy, butenyloxy, propynyloxy, butynyloxy, methylthio, ethylthio, n- or i- propylthio, n-, i-, s- or t-butylthio, propethylthio, butenylthio, propinylthio, butylthio, methylsulph inyl, ethylsulfinyl, methylsulphonyl or ethylsulphonyl substituted, where appropriate, by fluorine, chlorine, methoxy or ethoxy, or cyclopropyl. A very particularly preferred group of compounds according to the invention are the compounds of the formula (1), in which Q is oxygen p sulfur, R 1 is methyl, ethyl, n- or i-propyl, R 2 is methyl, ethyl, n- or i-propyl and R3 means triazolinyl substituted, if any, of the following formula,
N A N- FT N R3
Q 1 is oxygen or sulfur, and R 4 is methyl, ethyl, n- or i-propyl, respectively substituted, if appropriate, by fluorine, chlorine, methoxy or ethoxy, means propenyl or propynyl substituted respectively by fluorine or by chloro means methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, n- or i-propylamino, means propenyloxy, means dimethylamino or means cyclo-propyl, means chloro or bromo, means methyl, ethyl, non-i-propyl , n-, i-, s- or t-butyl substituted respectively by fluorine, chlorine, cyano, methoxy or ethoxy, means ethenyl, pro-penyl, butenyl, propynyl or butynyl substituted, respectively, if appropriate by fluorine, chlorine or bromine, means methoxy, ethoxy, n- or i-propoxy, ni-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino respectively substituted, if appropriate, by fluorine , by chlorine, by cyano, by methoxy or by ethoxy, means propenyloxy, butenyloxy, propynyloxy, butynyloxy, propenylthio, pro-padienylthio, butenylthio, propynylthio, butynylthio, pro-penylamino, butenylamino, propynylamino, or butynylamino, means dimethylamino, diethylamino or dipropylamino, means cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopro-pyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopenthylamino, cyclohexylamino, cyclopropyl ethyl, tilmetilo cyclobutyl, cyclopentylmethyl, cyclohexylmethyl, cyclo- propilmetoxi, cyclobutylmethoxy, cyclopentylmethoxy, ci- clohexilmetoxi, cyclopropylmethylthio, ciclobutilmetil- thio, ciclopentilmetiltio, ciclohexilmetiltio, cyclo- propylmethylamino, cyclobutylmethylamino, cyclopentylmethyl or cyclohexylmethylamino ino linden in each case optionally substituted by fluorine, by chlorine, by methyl and / or by ethyl, or phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino respectively substituted, if appropriate, by fluorine, chlorine, methyl, trifluoromethyl, methoxy and / or ethoxycarbonyl, or R4 and R5 mean together alkanediyl, if appropriate branched, with 3 to 11 carbon atoms. The definitions of the residues indicated above in a general manner or in the preferred ranges are valid both for the final products of the formula (1) and also correspondingly for the starting materials or the intermediate products necessary respectively for the preparation. These definitions of the remains can be combined arbitrarily with each other, that is to say even between the preferred ranges indicated.
If, for example, 4-bromo-2-methyl-thiophene-3-sulfonamide and 5-ethoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1, 2,4-triazole-3 are used -tiona, as starting products, the development of the reaction in the case of process (a) according to the invention can be schematized by means of the following formula scheme:
If, for example, 4-chloro-2-ethyl-3-thienylsulfonyl isothiocyanate and 5-ethyl-4-methoxy-2,4-dihydro-3H-1, 2,4-triazol-3-one are used as starting products, the reaction can be schematized in the case of process (b) according to the invention by means of the following formula scheme:
If they are used, for example, 4-ethyl-2-methoxy-thiophene-3-sulfochloride, 5-ethylthio-4-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one and the potassium cyanate as starting compounds, the development of the reaction in the case of process (c) according to the invention can be schematized by means of the following formula scheme:
If, for example, 4-cyano-2-iso-propyl-thiophene-3-sulfochloride and 5-methyl-1,2,4-oxadia-zol-3-carboxamide are used as starting compounds, the development of the reaction in the case of process (d) according to the invention by means of the following formula scheme:
If, for example, N- (4-fluoro-2-trifluoromethyl-thiophen-3-ylsulfonyl) -O-methyl-urethane and 4-methyl-5-methylthio-2,4-dihydro-3H are used -l, 2, 4-triazol-3-one as starting compounds, the development of the reaction in the case of process (e) according to the invention can be schematized by means of the following formula scheme:
S02-NH-COOCH3 N = J ^ _-? F S02 ^ N ^ NN N "CH, SCH, H N = SCH,
The sulfonamides to be used as starting materials in the process (a) according to the invention for the preparation of the compounds of the formula (I) are generally defined by the formula (II). In formula (II), R 1 and R 2 preferably have, or in particular, that meaning which has already been mentioned above in a preferred manner or, more particularly, for R 1 and R 2 in the description of the compounds of the formula (I) according to invention. The starting materials of the formula (II) are not yet known in the literature; as new products they are also an object of the present application. The novel sulfonamides of the formula (II) are obtained if sulfonyl chlorides of the formula (VI) are reacted
wherein R1 and R2 have the meaning indicated above, with ammonia, if appropriate in the presence of a diluent, such as for example water, at temperatures between 0 ° C and 50 ° C (see the preparation examples). The sulfonyl chlorides of the formula (VI) are also not known in the literature; as new products they are also an object of the present application. The novel sulfochlorides of the formula (VI) are obtained if corresponding amino-compounds of the general formula (X) are reacted
wherein R1 and R2 have the meaning indicated above, with an alkali metal nitrite, such as for example sodium nitrite, in the presence of hydrochloric acid at temperatures between -10 ° C and + 10 ° C and the solution of the The diazonium salt thus obtained is reacted with sulfur dioxide in the presence of a diluent, such as, for example, dichloromethane, 1,2-dichloroethane or acetic acid, and in the presence of a catalyst, such as, for example, Cuprous chloride (I) and / or cupric chloride (II), at temperatures between -10 ° C and + 50 ° C (see the preparation examples).
The amino compounds necessary as starting materials of the formula (X) are known and / or can be prepared according to processes known per se (see DE 33 03 388). The derivatives of the (thio) carboxylic acids to be used as starting materials furthermore in the process (a) according to the invention for the preparation of the compounds of the formula (I), are generally defined by means of the formula (III) ). In the formula (III), Q and R3 preferably have or especially that meaning which has already been indicated preferably or particularly preferably for Q and R3 in the description of the compounds of the formula (I) according to the invention; preferably Z means fluorine, chlorine, bromine, alkoxy with 1 to 4 carbon atoms, phenoxy or benzyloxy, especially chlorine, methoxy, ethoxy or phenoxy. The starting materials of the formula (III) are known and / or can be prepared by processes known per se (see EP 459244, EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266). The sulfonyl iso (thio) cyanates to be used as starting materials in the process (b) according to the invention for the preparation of the compounds of the formula (I) are generally defined by the formula '(IV) . In the formula (IV), Q, R1 and R2 preferably have or especially that meaning which has already been indicated above, preferably or especially preferably for Q, R1 and R2 in the description of the compounds of the formula ( I) according to the invention. The iso (thio) cyanates of sulfonyl of the formula (IV) are not yet known from the literature; these constitute, as new products, also an object of the present application. The new iso (thio) cyanates of the sulfonyl of the formula (IV) are obtained if sulfonamides of the general formula (II) are converted prior to phosgene or thiophosgene, if appropriate in the presence of an alkyl isocyanate, such as, for example, butyl isocyanate, optionally in the presence of a reaction aid, such as, for example, diazabicyclo [2, 2, 2] octane, and in the presence of a diluent, such as, for example, toluene, xylene or chlorobenzene, temperatures between 80 ° C and 150 ° C and, after completion of the reaction, the volatile components are removed by distillation under reduced pressure (see the preparation examples). The heterocycles, to be used as starting materials in processes (b), (c) and (e) according to the invention, are generally defined by means of formula (V). In the formula (V), R3"1 preferably means thiazolinyl, if substituted, of the following formula, Q1 ^ N ~ N: R5 where Q1 signifies oxygen or sulfur and the residues R4 and R5 preferably have or especially those meanings which have already been indicated above, preferably or particularly preferably for R 4 or for R 5 in the description of the compounds of the formula (I) according to the invention The starting materials of the formula (V) are known and or can be prepared according to known processes (see EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266) The sulfonyl chlorides to be used as starting materials in processes (c) and ( d) according to the invention, for the preparation of the compounds of the formula (I), they are generally defined by the formula (VI). In the formula (VI), R1 and R2 preferably have or especially that meaning which It has previously been indicated in a preferred manner or, more preferably, for R1 and R2 in the description of the compounds of the formula (I) according to the invention. The sulfonyl chlorides of the formula (VI) are not yet known from the literature; as new products they are also an object of the present application and can be prepared as described above. The amides of the (thio) carboxylic acids to be used as starting materials in the process (b) according to the invention for the preparation of the compounds of the formula (I) are generally defined by the formula (VIII) . In the formula (VIII), Q and R3 preferably have or especially that meaning which has been previously indicated in a preferred manner or in a particularly preferred manner for Q and R3 in the description of the compounds of the formula (I) according to the invention. The starting materials of the formula (VIII) are known and / or can be prepared according to processes known per se (cf. EP 459244). The sulfonylamino (thio) carbonyl compounds to be used as starting materials in the process (e) according to the invention for the preparation of the compounds of the formula (I) are generally defined by the formula (IX). In the formula (IX), Q, R1 and R2 preferably have or especially that meaning which has already been indicated above, preferably or especially preferably for Q, R1 and R2 in the description of the compounds of the invention. formula (I) according to the invention; preferably Z means fluorine, chlorine, bromine, alkoxy with 1 to 4 carbon atoms, phenoxy or benzyloxy, especially chlorine, methoxy, ethoxy or phenoxy. The starting materials of the formula (IX) are known and / or can be prepared according to methods known per se. The processes (a), (b), (c), (d) and (e) according to the invention for the preparation of the novel compounds of the formula (I) are preferably carried out using diluents. Suitable diluents are practically all inert organic solvents in this case. These preferably include halogenated aliphatic and aromatic hydrocarbons, such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, to-luene, xylene, methylene chloride, ethylene chloride, chloroform, tetrachloromethane, chlorobenzene and o-dichloro-benzene; ethers such as diethyl and dibutyl ether, glycol dimethyl ether and diglycoldimethyl ether, tetrahydrofuran and dioxane; ketones such as acetone, methyl-ethyl-, methyl-isopropyl- and methyl-isobutyl-ketone; esters such as methyl acetate and ethyl acetate; nitriles such as, for example, acetonitrile and propionitrile; amides, such as, for example, dimethylformamide, dimethylacetamide and N-methylpyrrolidone, as well as dimethylsulfoxide, tetramethylenesulphonane and hexamethylphosphorotriamide. All the acid-binding agents which can be used in such reactions can be used as acid-binding agents or as acid acceptors in processes (a), (b), (c), (d) and (e) according to the invention. Preference will be given to alkali metal hydroxides such as, for example, sodium and potassium hydroxide, alkaline earth metal hydroxide, such as, for example, calcium hydroxide, carbonates and alcoholates of alkali metals such as sodium and potassium carbonate, tere. sodium and potassium butylate, in addition basic nitrogenous compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, ethyl-diisopropylamine, ethyldicyclohexylamine, N, N-dimethylbenzylamine, N, N-dimethyl-aniline, pyridine , 2-methyl-, 3-methyl-, 4-methyl-, 2, 4-dimethyl-, 2,6-dimethyl-, 2-ethyl-, 4-ethyl- and 5-ethyl-2-methyl- pyridine, 1,5-diazabicyclo [4, 3,0] -non-5-ene (DBN), 1,8-diazabicyclo [5, 4, 0] -undec-7-ene (DBU) and 1,4-diazabicyclo [2,2,2] -octane (DABCO). The reaction temperatures in the processes (a), (b), (c), (d) and (e) according to the invention can vary within wide limits. In general, work is carried out at temperatures between -20 ° C and + 150 ° C, preferably at temperatures between 0 ° C and + 100 ° C. The processes according to the invention (a), (b), (c), (d) and (e) are generally carried out under normal pressure. However, it is also possible to work under higher pressure or at a lower pressure. To carry out the procedures (a),
(b), (c), (d) and (e) according to the invention the starting materials required in each case are generally used in approximately equimolar quantities. However, it is also possible to use one of the components used in each case in a larger excess. The reactions are generally carried out in a suitable diluent in the presence of an acid acceptor and the reaction mixture is stirred for several hours at the temperature required in each case. The preparation is carried out in processes (a), (b), (c), (d) and (e) according to the invention respectively according to customary methods (see the preparation examples). Compounds can be prepared, if appropriate, from the compounds according to the invention of the general formula (I). Such salts are obtained in a simple manner according to the usual methods of salt formation, for example by dissolving or dispersing a compound of the formula (I) in a suitable solvent, such as, for example, methylene chloride, acetone, tere. -buti1-methy1-ether or toluene, and addition of a suitable base. The salts can then be isolated, if necessary after prolonged stirring, by evaporation or by suction filtration. The active compounds according to the invention can be used as defoliants, desiccants, herbicidal agents and especially as agents for removing weeds. By weeds, in the broadest sense, we must understand the plants that grow in places where they are unwanted. The fact that the substances according to the invention act as total or selective herbicides depends essentially on the amount used. The active compounds according to the invention can be used, for example, in the following plants: Bad dicotyledonous herbs of the kinds; Sinapis Lepi-diu, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia , Lamium, Veronica, Abutilon, E ex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum. Cultures of dicotyledonous classes; Gossypium, Gly-cinema, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita. Bad monocotyledonous herbs of the kinds; Echino-chloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Oats, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera. Cultures of monocotyledonous classes; Oryza, Zea, Triticum, Hordeum, Oats, Sécale, Sorghum, Panicum, Sac-charum, Ananas, Asparagus, Allium. The use of the active compounds according to the invention, however, is not limited in any way to these classes, but they also extend equally over other plants. The compounds are suitable, depending on the concentration, to completely combat the weeds, for example, in industrial and road installations and in roads and squares, with and without tree growth. In the same way, compounds can be used to control weeds in permanent crops, for example in forestry, ornamental trees, fruit trees, vineyards, citrus trees, walnut trees, plantains, coffee, tea, rubber oil palms, cocoa, berries and hops, on ornamental and sports paths and on meadows and to selectively control weeds in mono-annual crops. The compounds according to the invention of the formula (I), according to the invention, are particularly suitable for the selective control of monocotyledonous and dicotyledonous weeds in onocotyledonous cultures both in the pre-emergence procedure and in the post-emergence process. The active products can be transformed into the usual formulations, such as solutions, emulsions, sprayable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with the active product, as well as micro-encapsulated materials polymers. These formulations are prepared in known manner, for example, by mixing the active ingredients with extender materials, that is, with liquid solvents and / or solid excipients, where appropriate, using surfactants, that is, emulsifiers and / or dispersants. santes and / or means generating foam.
When using water as a filler, it is also possible, for example, to use organic solvents as auxiliary solvents. The following are particularly suitable liquid solvents: aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane, or paraffins, for example, fractions of crude oil, mineral and vegetable oils, alcohols such as butanol, or glycol, as well as their esters and ethers, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone, strong polar solvents such as dimethylformamide and dimethyl sulfoxide, as well as water. Suitable solid excipients are, for example, ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earths and molten synthetic minerals, such as silicic acid, highly dispersed , aluminum oxide and silicates, as solid excipients for granulates come into consideration: for example, broken and fractionated natural minerals such as calcite, marble, pumice foot, sepiolite, dolomite, as well as synthetic granules of inorganic and organic flours, as well as as granulates of organic materials, such as sawdust, coconut husks, corn ears and tobacco stems; suitable emulsifiers and / or foam generators are, for example, non-ionogenic and anionic emulsifiers, such as polyoxyethylenated esters of fatty acids, for example, alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfone-tos, as well as albumin hydrolysates.; Suitable dispersants are, for example, sulfitic leaching of lignin and methylcellulose. Adhesives such as carboxymethylcellulose, natural and synthetic polymers, powdered, granulated or in the form of latex, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids, such as cephalin and lecithin, and synthetic phospholipids can be used in the formulations. . Other additives can be mineral and vegetable oils. Dyes, such as inorganic pigments, for example, iron oxide, titanium oxide, ferrocyanic blue and organic dyes, such as alizarin dyes, metallic azo and phthalocyanine dyes and trace nutrients, such as iron salts, can be employed. manganese, boron, copper, cobalt, molybdenum and zinc. The formulations generally contain between 0.1 to 95% by weight of active compound, preferably between 0.5 and 90%. The active compounds according to the invention can be used as such or in their formulations also for combating weeds in admixture with herbicides, ready-to-use preparations or tank mixtures being possible. Suitable mixtures are known herbicides, for example: Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydi (-sodium), Ametryne, Amidochlor, Amidosulfuron, Asulam, Atrazine, Azimsulfuron, Benazolin, Benfuresate, Bensulfuron (-methyl) ), Bentazon, Benzofenap, Benzoylprop- (ethyl), Bialaphos, Bifenox, Bromobutide, Bromophenoxy, Bromoxynil, Butachlor, Butylate, Cafenstrole, Carbetami-de, Chlomethoxyfen, Chloramben, Chloridazon, Chlorimu-rum (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinmethylin, Cinosulfuron, Clethodim, Clodinafop (propargyl), Clomazone, Clopyralid, Clopyrasulfuron, Cloransu-lam (-methyl), Cumyluron, Cyanazine, Cycloate, Cyclosulfa-muron, Cycloxydim, Cyhalofop (-butyl), 2,4-D , 2,4-DB, 2,4-DP, Desmedipham, Diallate, Dicamba, Diclofop (-meti-lo), Difenzoquat, Diflufenican, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dinitramine, Diphenamid, diquat, dithiopyr, diuron, dymron, EPTC, Es-procarb, ethalfluralin, ethametsulfuron (-methyl), Ethofu-mesate, Ethoxyfen, etobenzanid, Fenoxaprop- (ethyl), Fram-prop (-isopropyl), Flamprop (-isopropyl-L), Flamprop (me-linden), flazasulfuron, fluazifop (butyl), Flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, Fluome-turon, fluorochloridone, fluoroglycofen (-ethyl), Flupo-xam , Flupropacil, Flurenol, Fluridone, Fluroxypyr, Flur-primidol, Flurtamone, Fomesafen, Glufosinate (ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl) - Hexazinone, Imazamethabenz (-methyl), Imazamet-hapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazo-sulfuron, Ioxynil, Isopropalin, Isoproturon, Isoxaben, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Metamitron, Metazachlor, Metha-benzthiazuron, Metobenzuron, Metobromuron, Metolachlor, Metosulam, Metoxuron, Metsulfuron (-methyl), Metribuzin, Molinate, Monoli Nuron, Naproanilide, Napropamide, Nebu-ron, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiazon, Oxyfluorfen, Paraquat, Pendimethalin, Phen e-dipham, Piperophos, Pretilachlor, Primisulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Propyzamide , Prosulfocarb, Prosulfuron, Pyrazolate, Pyra-zosulfuron (-ethyl), pyrazoxyfen, pyributicarb, Pyridate, pyrithiobac (-sodium), Quinchlorac, quinmerac, Quizalofop- (ethyl), quizalofop (-P-tefuryl), rimsulfuron, Sethoxy-dim , Simazine, simetryn, sulcotrione, Sulfentrazone, Sul-fometuron (-methyl), Sulfosate, tebutam, Tebuthiuron, Ter-buthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thia-zopyr, hidiazimin, thifensulfuron (-methyl), hiobencarb, tiocarbazil, tralkoxydim , Triallate, Triasulfuron, Tribe-nuron (-methyl), Triclopyr, Tridiphane, Trifluralin and Tri-flusulfuron. A mixture with other known active substances is also possible, such as fungicides, insecticides, acaricides, nematicides, protective substances against ingestion by birds, nutrient substances of the plants and means for improving the structure of the ground. The active compounds can be used as such, in the form of their formulations or of the forms of application prepared therefrom by further dilutions, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. The use is carried out in the usual way, for example, by watering, spraying, spraying, spreading. The active products according to the invention can be applied both before and after the outbreak of the plans. They can also be incorporated into the soil before sowing. The quantities of active product used can vary within a wide range. These depend fundamentally on the type of the desired effect. In general, the amounts used are between 1 g and 10 kg of active product per hectare of land surface, preferably between 5 g and 5 kg per hectare. The preparation and use of the active substances according to the invention is apparent from the following examples: Preparation examples. Example 1
(Procedure (a)). They are added to a solution of 1.6 g (6.4 mmoles) of 5-ethoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1, 2,4-triazole-3-. ona, in 30 ml of acetonitrile, successively, 1.3 g (6.8 mmoles) of 2,4-dimethyl-thiophene-3-sulfonamide and 1.1 g (7 mmoles) of 1,8-diazabicyclo- [5, 4, 0] -un-dec-7-ene (DBU). The reaction mixture is stirred for about 15 hours at room temperature (approximately 20 ° C) and then concentrated by evaporation under vacuum of the water tube. The residue is then taken up in methylene chloride, washed with IN hydrochloric acid and then with water. The organic phase is dried with magnesium sulfate and filtered. The filtrate is concentrated by evaporation under vacuum of the water pump and the residue is recrystallized from isopropanol. 1.1 g (50% of theory) of 5-ethoxy-4-methyl-2- (2,4-dimethyl-thien-3-yl-sulfonylaminocarbonyl) -2,4-dihydro-3H- are obtained 1,2,4-triazol-3-one with a melting point of 158 ° C. Example 2
(Procedure (d)) 2.0 g (36 mmol) of potassium hydroxide powder, at 20 ° C up to 35 ° C maximum, are added to a solution of 1.52 g (12.0 mmol) of 5- methyl-1,2,4-oxadiazole-3-carboxamide in 150 ml of dioxane. After 30 minutes, about 50 ml of dioxane is distilled off under vacuum from the water tube at 30 ° C to 35 ° C. The mixture is then combined, in portions, with 2.65 g (12.6 mmol) of 2,4-dimethyl-thiophene-3-sulfochloride and the reaction mixture is stirred for approximately 12 hours at room temperature (20). ° C approximately). It is then concentrated by evaporation under vacuum of the water pump, the residue is taken up in water and acidified with 2N hydrochloric acid. It is then extracted twice with 100 ml of methylene chloride each time. The combined organic solutions are washed with water, dried with magnesium sulfate and filtered. The filtrate is concentrated by evaporation under vacuum of the water pump and the residue is recrystallized from ethanol. 0.7 g (19% of theory) of N- (2,4-dimethyl-thien-3-ylsulfonyl) -5-methyl-1,2,4-oxadiazole-3-carboxamide are obtained with a dot of fusion of 164 ° C. In a manner analogous to that of Examples 1 and 2 and according to the general description of the preparation processes according to the invention, for example, the form-mule (I) compounds set out in Table 1 below can also be prepared.
Table 1; Examples of compounds of the formula (I)
bla 1 Continuation)
Table 1 (Continued)
Table 1 (Continued)
Table 1 (Continued)
Table 1 (Continued)
Table 1 (Continued)
Starting products of the formula (II); Example (Il-li.
A mixture of 6.0 g (29 mmol) of 2,4-dimethyl-thiophene-3-sulfochloride and 30 ml of 25% strength aqueous ammonia solution is stirred for 12 hours at room temperature, about 20 ° C. . The crystalline product formed in this case is then isolated by suction filtration. 4.3 g (80% of theory) of 2,4-dimethyl-thiophene-3-sulfonamide having a melting point of 135 ° C are obtained. Starting products of the formula (IV); Example (1V-1).
A mixture consisting of 19.1 g (100 mmol) of 2,4-dimethyl-thiophene-3-sulfone-mide, 10.0 g (100 mmol) of butyl isocyanate and 100 ml of chloroform is heated to boiling. Phosgene is passed through the mixture at reflux temperature for 4 hours. It is then concentrated by evaporation under vacuum of the water pump and the residue is subjected to a vacuum distillation of the oil pump. 10.3 g (47% of theory) of 2,4-dimethyl-thien-3-yl-sulfonyl isocyanate are obtained with a boiling range of 135 ° C to 140 ° C (at 1 mbar). Starting products of the formula (VI); Example (Vi-D.
A solution of 13.9 g (109 mmol) of 3-amino-2,4-dimethyl-thiophene in 30 ml of 10% hydrochloric acid is cooled to 0 ° C and 50 ml of concentrated hydrochloric acid are combined. Then it is added drop by drop, under cooling at 0 ° C, at -5 ° C, under stirring, a solution of 8.6 g (125-mmoles) of sodium nitrite in 22 ml of water. The reaction mixture is stirred for approximately 1 hour at 0 ° C to -5 ° C. The excess sodium nitrite is then destroyed with amidosulfonic acid. The diazonium salt solution obtained in this way is added, dropwise, at about 15 ° C, a solution of 12 g of sulfur dioxide in 100 ml of 1,2-dichloroethane. Then 600 mg of cuprous chloride (I) and 600 mg of dodecyltrimethylammonium bromide are added and the reaction mixture is stirred for approximately 1 hour at about 40 ° C and for a further 12 hours at room temperature (approximately at 20 ° C). After addition of 6 g of 30% solution of hydrogen peroxide, the mixture is stirred for another 30 minutes. The organic phase is then separated, washed twice with water, dried with magnesium sulfate and filtered. The filtrate is concentrated by evaporation under vacuum of the water pump, the residue is digested in petroleum ether and the crystalline product formed is isolated by suction filtration. 9.6 g (42% of theory) of 2,4-dimethyl-thiophene-3-sulfochloride with a melting point of 79 ° C are obtained. Respectively, analogously to examples (II-1), (IV-1) and (VI-1), it was also possible to prepare, for example, the compounds of formulas (II), (IV) and (VI) indicated in Table 2 below:
Table 2; Examples of compounds of the formulas (II), (IV) and (VI) [ie the residues R1 and R2 are valid for each of these formulas]; Q means o or S.
Application examples; Example A. Pre-emergence trial. Solvent; 5 parts by weight of acetone. Emulsifier: 1 part by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent, the amount of emulsifier indicated is added and the concentrate is diluted with water to the desired concentration. Seeds of the test plants are sown in normal soil. After approximately 24 hours, the soil is sprayed with the active product preparation. In this case, the quantity of water per unit area is suitably constant. The concentration of the preparation does not play any role, the sun being the fundamental amount of application of the active product per unit area. After three weeks, the degree of damage of the plants is evaluated in% of damages compared to the development of the untreated control. They mean: 0% = no effect (same as untreated controls). 100% = total destruction.
In this test, for example, the compounds according to Preparation Examples 1, 3, 4, 5, 11 and 12 show a partially good compatibility with crop plants, such as, for example, corn and wheat, a potent efesto. against weeds (see table A). ai. "= active product (" active ingredient). Table A; Pre-sprout / greenhouse test Product Quantity Corn Bro- Cype- Lo- Se- Cheno- Matri- Sola-active used mus rus lium tarla podium caria mum according to ex. (g al / ha) of obtaining nfi
O NH
? Jl 125 100 100 100 100 100 100 100
H3C C2HS
(3)
Table A; (Continued) Pre-sprout / greenhouse test Product Quantity Wheat Bro- Cype- Lo- Se- Cheno- Matri- Sola- active used mus rus lium taria podium caria mum according to ex. (g ai / ha) of obtaining na
100 95 100 100 100 100 100
0) Table A (Continued) Pre-sprout / greenhouse test Product Quantity Corn Wheat Bro- Cype- Lo- Se- Cheno- Ma- Sola- active used mus rus lium ta podium tri- mum according to j. (g ai / ha) ria caria of obtaining na
(4) Table A (Continued) Pre-sprout / greenhouse test Product Quantity Bro- Cype- Lo- Seta- Cheno- Matri - Sola- active used mus rus lium ria podium caria according to ex. (g ai / ha) of obtaining ns
0 V j, H Y 125 100 100 100 100 95 100 95
H3C O - CH,
(H)
Table A (Continued) Pre-sprout / greenhouse test Active product Quantity Alope- Abuti- Amaran- Sina-Xan-vo according to ex. employed curus Ion thus obtaining thium pis (g ai / .ha) na
° ^ = J N 250 70 90 90 95 90
H, C O- "> -CH,
(5)
Y
(12)
Example B. Post-emergence test. Solvent: 5 parts by weight of acetone. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amount of solvent, the amount of emulsifier indicated is added and the concentrate is diluted with water to the desired concentration. With the active product preparation, test plants are sprayed, having a height of 5-15 cm, so that the desired quantities of active compound per unit of surface are applied respec- tively. The concentration of the sprayable broths is chosen in such a way that the desired quantity in each case of active product is applied in 1,000 liters of water / ha. After three weeks, the degree of damage of the plants is evaluated in% of damages compared to the development of the untreated controls. Signifisan: 0% = no efesto (same as the untreated strings). 100% = total destrussión. In this test they show, for example, the somersaults according to the examples of obtention 6, 13 and 14, with a comparatively good compatibility with the sultivo plants, such as for example maize, a powerful efesto sontra the weeds (see Table B). Table B; Pre-sprout / greenhouse trial Produsto acti- Amount Corn Setaria Abuti- Amaran- Sina-vo according to e. employed Ion thus obtaining pis (g ai /. ha) na
(6)
(13) Table B (Continued) Pre-sprout / greenhouse test Product active- Amount Corn Setaria Abuti- Amaran- Sina-vo according to e. employed Ion thus obtaining pis (g ai / .ha) na
(14)
It is noted that in relation to this date, the best method conosido by the solisitant to bring to the prststisa the sitada invention, is the one that is slaro of the present dessripsión of the invention.
Claims (1)
1.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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DE19650196.20 | 1996-12-04 |
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