MXPA99000641A - Triazoloazinsulfonamidas substitui - Google Patents
Triazoloazinsulfonamidas substituiInfo
- Publication number
- MXPA99000641A MXPA99000641A MXPA/A/1999/000641A MX9900641A MXPA99000641A MX PA99000641 A MXPA99000641 A MX PA99000641A MX 9900641 A MX9900641 A MX 9900641A MX PA99000641 A MXPA99000641 A MX PA99000641A
- Authority
- MX
- Mexico
- Prior art keywords
- carbon atoms
- cyano
- alkyl
- halogen
- methyl
- Prior art date
Links
- 125000004432 carbon atoms Chemical group C* 0.000 claims abstract description 248
- -1 4-cyano-2,5-difluoro-phenyl Chemical group 0.000 claims abstract description 130
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 106
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 96
- 150000002367 halogens Chemical class 0.000 claims abstract description 96
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 82
- 239000001257 hydrogen Substances 0.000 claims abstract description 82
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 45
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 20
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 239000011780 sodium chloride Substances 0.000 claims abstract description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 8
- 125000004429 atoms Chemical group 0.000 claims abstract description 7
- 125000005842 heteroatoms Chemical group 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 3
- 229940093912 Gynecological Sulfonamides Drugs 0.000 claims abstract 2
- 125000003277 amino group Chemical group 0.000 claims abstract 2
- 229940079867 intestinal antiinfectives Sulfonamides Drugs 0.000 claims abstract 2
- 229940005938 ophthalmologic antiinfectives Sulfonamides Drugs 0.000 claims abstract 2
- 150000003456 sulfonamides Chemical class 0.000 claims abstract 2
- 229940026752 topical Sulfonamides Drugs 0.000 claims abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 89
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 83
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 80
- 239000000460 chlorine Substances 0.000 claims description 77
- 229910052801 chlorine Inorganic materials 0.000 claims description 77
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 77
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 74
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 70
- 150000002431 hydrogen Chemical class 0.000 claims description 68
- 229910052731 fluorine Inorganic materials 0.000 claims description 55
- 239000011737 fluorine Substances 0.000 claims description 55
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 49
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 44
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 44
- 241000196324 Embryophyta Species 0.000 claims description 38
- CPPKAGUPTKIMNP-UHFFFAOYSA-N Cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 24
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 22
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- ZOAMZFNAPHWBEN-UHFFFAOYSA-N 2-$l^{1}-oxidanylpropane Chemical group CC(C)[O] ZOAMZFNAPHWBEN-UHFFFAOYSA-N 0.000 claims description 15
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 10
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 10
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- MERLDXJKKQQWLA-UHFFFAOYSA-N prop-1-en-2-yloxymethylidyneoxidanium Chemical group [CH2-]C(=C)OC#[O+] MERLDXJKKQQWLA-UHFFFAOYSA-N 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 6
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 6
- 241000607479 Yersinia pestis Species 0.000 claims description 5
- 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 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 4
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 4
- 244000005700 microbiome Species 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000004606 Fillers/Extenders Substances 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- YIYSEJAAJSSNNS-UHFFFAOYSA-N but-1-en-1-one Chemical group [CH2]CC=C=O YIYSEJAAJSSNNS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 230000001131 transforming Effects 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 241000188250 Idas Species 0.000 claims 1
- 101710028696 MCIDAS Proteins 0.000 claims 1
- 150000003841 chloride salts Chemical class 0.000 claims 1
- HZNQVAOLVRFZBE-UHFFFAOYSA-N ethenylcyclohexane Chemical group C=C[C]1CCCCC1 HZNQVAOLVRFZBE-UHFFFAOYSA-N 0.000 claims 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 abstract 2
- 239000000047 product Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 241001049165 Caria Species 0.000 description 14
- 239000003995 emulsifying agent Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 241001101998 Galium Species 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 241000209140 Triticum Species 0.000 description 7
- 150000001804 chlorine Chemical compound 0.000 description 7
- 230000003389 potentiating Effects 0.000 description 7
- 235000021307 wheat Nutrition 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000002877 alkyl aryl group Chemical group 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 241000234653 Cyperus Species 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 230000002363 herbicidal Effects 0.000 description 5
- XPDWGBQVDMORPB-UHFFFAOYSA-N methyl trifluoride Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 5
- 239000010695 polyglycol Substances 0.000 description 5
- 241000208296 Datura Species 0.000 description 4
- 240000001307 Myosotis scorpioides Species 0.000 description 4
- 241000500437 Plutella xylostella Species 0.000 description 4
- 101700003439 SOGA1 Proteins 0.000 description 4
- 240000006394 Sorghum bicolor Species 0.000 description 4
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- WJJBIYLGJUVNJX-UHFFFAOYSA-N pyrimidine-2-sulfonamide Chemical compound NS(=O)(=O)C1=NC=CC=N1 WJJBIYLGJUVNJX-UHFFFAOYSA-N 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000209200 Bromus Species 0.000 description 3
- 229960005069 Calcium Drugs 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N DABCO Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
- 241000207783 Ipomoea Species 0.000 description 3
- 241000209082 Lolium Species 0.000 description 3
- 241000209048 Poa Species 0.000 description 3
- 241000579741 Sphaerotheca <fungi> Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 230000001681 protective Effects 0.000 description 3
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- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002965 rope Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000000967 suction filtration Methods 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
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-Aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 241000219144 Abutilon Species 0.000 description 2
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- 241000239223 Arachnida Species 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 240000008067 Cucumis sativus Species 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- 241001465183 Drechslera Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 240000007842 Glycine max Species 0.000 description 2
- 241000219146 Gossypium Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- 241000258937 Hemiptera Species 0.000 description 2
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- 235000011430 Malus pumila Nutrition 0.000 description 2
- 235000015103 Malus silvestris Nutrition 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
- 241000244206 Nematoda Species 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
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- 241000896242 Podosphaera Species 0.000 description 2
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M Potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
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- 150000001298 alcohols Chemical class 0.000 description 2
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- 238000000576 coating method Methods 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
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- XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
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- 230000001717 pathogenic Effects 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000012439 solid excipient Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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Abstract
The invention relates to novel substituted triazoloazine sulfonamides of the formula (I): wherein Q 1 signifies nitrogen or a group CH-, R 1 signifies hydrogen or a group CH-, R 1 signifies hydrogen, halogen or means alkyl with 1 to 4 atoms of carbon, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, alkylamino with 1 to 4 carbon atoms or di- (alkyl with 1 to 4 carbon atoms) amino substituted, if appropriate by hydroxy, by halogen, respectively or by alkoxy with 1 to 4 carbon atoms, R2 means hydrogen, halogen, or means alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, alkylamino with 1 to 4 carbon atoms or di- (alkyl with 1 to 4 carbon atoms) -amino substituted, where appropriate, by halogen and Ar means 4-cyano-2,5-difluoro-phenyl, 2,6-dimethoxy-phenyl, 2-bromo-3-tri - fluorine-methyl-phenyl, 2-bromo-5-trifluoromethyl-phenyl, 6- clo ro-pyridin-3-yl-methyl or means one of the (hetero) cyclic groupings with 5 to 6 members cited in the description, as well as their salts, a process for obtaining the new compounds and their use as agents for the treatment of plants
Description
TRIAZOLOAZINSULFONAMIDAS SUBSTITUIDAS. FIELD OF THE INVENTION The invention relates to new substituted triazoloazinesulfonamides, to processes for their preparation and to their use as agents for the treatment of plants. Description of the prior art. A large number of triazoloazinsulphone are already known from the literature (patents) (see publications EP 142152, EP 244847, EP 375076, US 4605433, US 5163995, WO 89/10368, Pestic. Sci. 29 (1990) , 341-355). Detailed description of the invention. New substituted triazoloazinsulfonamides of the general formula (I) have been found
wherein Q1 signifies nitrogen or a grouping CH-, Q2 signifies nitrogen or a grouping CH-, R1 signifies hydrogen, halogen or means alkyl with
1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, alkylamino with 1 to 4 carbon atoms or di (alkyl with REF: 29149
1 to 4 carbon atoms) -amino substituted respectively by hydroxy, by halogen or by alkoxy with 1 to 4 carbon atoms, R2 means hydrogen, halogen or means alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, alkylamino with 1 to 4 carbon atoms or di- (alkyl with 1 to 4 carbon atoms) -amino substituted respectively by halogen, and Ar means 4- cyano-2, 5-difluoro-phenyl, 2,6-dimethoxy-phenyl, 2-bromo-3-trifluoromethyl-phenyl, 2-bromo-5-trifluoromethyl-phenyl, 4-bromo-2, 6- dimethyl-phenyl, 6-chloro-pyridin-3-yl-methyl or one of the cyclic groupings (hetero) with 5 or 6 following members:
where m means respectively the numbers 1 or 2, n means respectively the numbers 0, 1 or 2, A1 means alkyl having 1 to 4 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms or means cycloalkyl with 3 to 6 carbon atoms, optionally substituted by cyano, by halogen or by alkyl with 1 to 4 carbon atoms, A2 means alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, carbon, alkylthio with 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms
carbon or alkylsulfonyl with 1 to 4 carbon atoms substituted, where appropriate, by halogen. RJ means alkyl having 1 to 4 carbon atoms optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, A4 means alkyl having 1 to 4 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, ^ A5 means alkyl with 2 to 4 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, means alkenyl with 2 a 4 carbon atoms optionally substituted by halogen or means cycloalkyl with 3 to 6 carbon atoms-alkyl having 1 to 4 carbon atoms * optionally substituted by cyano, by halogen or by alkyl with 1 to 4 atoms of carbon, A6 means halogen or means alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms or alkenyloxy with 2 to 4 carbon atoms, respectively substituted by halogen, A7 means alkyl co n 1 to 4 carbon atoms substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms,
A8 means cyano, nitro or alkyl with 1 to 4 carbon atoms, optionally substituted by halogen, A9 means cyano, halogen or means alkyl having 1 to 4 carbon atoms, optionally substituted by halogen, A10 means alkyl with 1 at 4 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms or by cycloalkyl having 3 to 6 carbon atoms, optionally substituted by cyano, by halogen or by alkyl with 1 to 4 carbon atoms carbon atoms, A11 means hydrogen or means alkyl with 1 to 4 carbon atoms, alkylcarbonyl with 1 to 4 carbon atoms, alkoxycarbonyl with 1 to 4 carbon atoms or alkylsulfonyl with 1 to 4 carbon atoms substituted, where appropriate, by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms. carbon, A12 means hydrogen, cyano, halogen or means alkyl with 1 to 4 carbon atoms, optionally substituted by halogen, A13 means cyano, carbamoyl, 5,6-dihydro-1,4,4-dioxazin- 3-yl, halogen, alkyl having 1 to 4 carbon atoms, alkyl-carbonyl with 1 to 4 carbon atoms or alkoxy-carbonyl with 1 to 4 carbon atoms,
A 14 means hydrogen, meaning cyano, carbamoyl, halogen, alkyl having 1 to 4 carbon atoms, alkylcarbonyl with 1 to 4 carbon atoms or alkoxycarbonyl with 1 to 4 carbon atoms, A15 means hydrogen, meaning cyano, carbamoyl , halogen, alkyl with 1 to 4 carbon atoms, alkylcarbonyl with 1 to 4 carbon atoms or alkoxycarbonyl with 1 to 4 carbon atoms or together with A14 means a benzo-ringed ring, A16 means hydrogen, cyano, halogen or means alkyl with 1 to 4 carbon atoms, alkoxy with 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, alkylsulfinyl with 1 to 4 carbon atoms, or alkylsulfonyl with 1 to 4 carbon atoms substituted respectively, where appropriate, by halogen,
A17 means hydrogen, cyano, halogen or means alkyl having 1 to 4 carbon atoms, optionally substituted by halogen, A18 is hydrogen, cyano, halogen or means alkyl having 1 to 4 carbon atoms, optionally substituted by halogen, A 19 means hydrogen or alkyl having 1 to 4 carbon atoms, A ^ u means alkyl having 1 to 4 carbon atoms or alkenyl with 2 to 4 carbon atoms,
A21 means cyano, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms, A22 means alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms, A23 means alkyl with 1 to 4 carbon atoms,
A24 individually means alkyl having 1 to 4 carbon atoms or together with A23 means alkanediyl having 2 to 4 carbon atoms, A25 means cyano, halogen, alkyl c; > n 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms, A26 means alkyl with 1 to 4 carbon atoms,
A27 means cyano, halogen, alkyl having 1 to 4 carbon atoms, halogenoalkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms, A28 means hydrogen, difluoromethyl, alkylcarbonyl with 1 to 4 carbon atoms, alkoxycarbonyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, A29 means cyano, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms, A30 means hydrogen, alkyl with 1 to 4 carbon atoms
bond or alkoxy with 1 to 4 carbon atoms, A31 means hydrogen or alkyl with 1 to 4 carbon atoms, A32 means cyano, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms, A33 means hydrogen, alkyl having 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms, A34 means hydrogen or alkyl having 1 to 4 carbon atoms, A35 means cyano, halogen, alkyl with 1 to 4 carbon atoms or haloalkyl with 1 to 4 carbon atoms, A36 means hydrogen, alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms or phenyl, A37 means hydrogen, alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms or phenyl, A38 means hydrogen, halogen, means alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or alkylthio with 1 to 4 carbon atoms substituted, where appropriate, by cyano, by halogen or by alkoxy with 1 to 4 carbon volumes, or cycloalkyl having 3 to 6 carbon atoms,
cycloalkyloxy with 3 to 6 carbon atoms or cycloalkyl with 3 to 6 carbon atoms-alkyl having 1 to 4 carbon atoms substituted, where appropriate, by cyano, by halogen or by alkyl having 1 to 4 carbon atoms, and A39 means hydrogen, means alkyl having 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms, substituted, where appropriate, by cyano, halogen or alkoxy with 1 to 4 carbon atoms, or cycloalkyl with 3 to 6 carbon atoms; carbon atoms, cycloalkyloxy with 3 to 6 carbon atoms or cycloalkyl with 3 to 6 carbon atoms-alkyl having 1 to 4 carbon atoms, optionally substituted by cyano, by halogen or by alkyl with 1 to 4 carbon atoms carbon, as well as the salts of the compounds of the formula (I). The new substituted triazolazinsulfone ions of the general formula (I) are obtained if substituted triazoloazinsulfonyl chlorides of the general formula (II) are reacted
in which
Q11 Q2 f R1 and R2 have the meaning indicated above, with amino (hetero) arenos of the general formula (III)
H2N-Ar (III)
wherein Ar has the abovementioned meaning, if appropriate in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent, and, if appropriate, they are carried out in the compounds of the formula (I), obtained in this way, other reactions of transformation in the scope of the definition of the substituents previously indicated, according to usual methods. The new substituted triazsloazinsulfonamides of the formula (I) have interesting biological properties, which make possible their use as agents for the treatment of plants. These show a potent herbicidal, fungicidal and insecticidal activity and are characterized especially by an excellent and selective herbicidal effect. The subject of the invention are preferably compounds of the formula (I), in which Q1 signifies nitrogen or a group CH-, Q2 signifies nitrogen or a group CH-,
R1 means hydrogen, fluorine, chlorine, bromine or means methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n-, or i-propylthio, methylamino, ethylamino, n - or i-propylamino, dimethylamino or diethylamino respectively substituted, if appropriate, by fluorine, chlorine, methoxy or ethoxy, R2 means hydrogen, fluorine, chlorine, bromine or means methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i- propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino, or diethylamino respectively substituted, if appropriate, by fluorine, chlorine, methoxy or etoxi,
Ar means 4-cyano-2, 5-difluoro-phenyl, 2,6-dimethylsphenylene, 2-bromo-3-trifluoromethyl-phenyl, 2-bromo-5-trifluoromethyl-phenyl, 4-bromo- 2,6-dimethyl-phenyl, 6-chloro-pyridin-3-yl-methyl or one of the following groupings:
where m means respectively the numbers 1 or 2, n respectively means the numbers 0, 1 or 2, A1 means methyl, ethyl, n- or i-propyl, respectively substituted, if appropriate, by cyano, by fluorine, by chlorine, by bromine by methoxy or by ethoxy or cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl respectively substituted, where appropriate, by cyano, fluorine, chlorine, bromine, methyl or ethyl, A2 means methyl, ethyl, n- or i-propyl , methoxy, etho-
xi, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulphonyl, respectively substituted, if appropriate by fluorine, chlorine or bromine, A3 means methyl, ethyl, n- or i-propyl substituted, respectively, by cyano, by fluorine, by chlorine or by bromine, by methoxy or by ethoxy, A4 means methyl, ethyl, n- or i-propyl substituted respectively by cyano, fluorine, chlorine, bromine, methoxy or ethoxy, A5 means ethyl, n- or i-propyl, n-, i-, s- or t -butyl substituted, where appropriate, by cyano, by fluorine, by chlorine, by bromine, by methoxy or by ethoxy, means propenyl or butenyl substituted, where appropriate, by halogen, or means cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl substituted respectively if necessary by cyano, by fluorine, by chlorine, by bromine, by methyl or by ethyl, A6 means fluorine, chlorine, bromine or means methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, propenyl, butenyl, propenyloxy or butenyloxy respectively substituted by fluorine or for chlorine,
A7 means methyl, ethyl, n- or i-propyl substituted, where appropriate, by cyano, fluorine, chlorine, bromine, methoxy or ethoxy, A8 means cyano, nitro or methyl, ethyl, n- or i. -propyl substituted respectively where appropriate by fluorine or chlorine, A9 means cyano, fluorine, chlorine or means methyl, ethyl, n- or i-propyl respectively substituted, if appropriate by fluorine or chlorine, A10 means hydrogen, means methyl, ethyl, n- or i-propyl substituted respectively by cyano, by fluorine , by chlorine, by methoxy or by ethoxy, or means cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl respectively substituted, if appropriate by cyano, by fluorine, by chlorine, by methyl or by ethyl, A11 means hydrogen or means methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulphonyl respectively substituted by cyano, fluorine, chlorine, methoxy or ethoxy, A12 means hydrogen, cyano, fluorine, chlorine, bromine or means methyl, ethyl, n- or i-propyl substituted respectively by fluorine or chlorine,
A13 means cyano, carbamoyl, 5,6-dihydro-1,4,4-dioxazin-3-yl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-Butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, A14 means hydrogen, meaning cyano, carbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- i-Butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, A15 means hydrogen, meaning cyano, carbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i- butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl or together with A14 means a benzo-ringed ring, A16 means hydrogen, cyano, fluorine, chlorine, bromine or means methyl, ethyl, -n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulphonyl substituted respectively if appropriate by fluorine or chlorine, A17 means hydrogen, cyano, fluorine, chlorine, bromine or means methyl, ethyl, n- or i-propyl, respectively substituted, if appropriate, by fluorine or chlorine, A18 means hydrogen, cyano, fluorine , chlorine, bromine or
means methyl, ethyl, n- or i-propyl, respectively substituted, if appropriate, by fluorine or chlorine, A19 means hydrogen, methyl, ethyl, n- or i-propyl, A20 means methyl, ethyl, n- or i-propyl , or means propenyl or butenyl, A21 means cyano, fluoro, chloro, bromo, methyl, ethyl, n- or i-propyl, or means trifluoromethyl, A22 means methyl, ethyl, n- or i-propyl, A23 means methyl, ethyl , n- or i-propyl, A24 individually means methyl, ethyl, n- or i-propyl or together with A23 means ethane-1,2-diyl (dimethylene) or propane-1,3-diyl (trimethylene), A25 means cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, or means trifluoromethyl, A26 means methyl, ethyl, n- or i-propyl, A27 means cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, or means trifluoromethyl, A28 means hydrogen, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylsulfonyl, ethylsulfonyl, n - or i-propylsulfonyl, A29 means cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl or means trifluoromethyl, A30 means hydrogen, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n - or i-propoxy,
A31 means hydrogen or methyl, ethyl, n- or i-propyl, A32 means cyano, fluoro, chloro, bromo, methyl, ethyl, n- or i-propyl, or means trifluoromethyl, • A33 means hydrogen, methyl, ethyl, n - or i-propyl, methoxy, ethoxy, n- or i-propoxy, A34 means hydrogen, methyl, ethyl, n- or i-propyl, A35 means cyano, fluoro, chloro, bromo, methyl, ethyl, n- i-propyl, or means trifluoromethyl, A36 means hydrogen, methyl, ethyl, n- or i-propyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl, A37 means hydrogen, methyl, ethyl, n- or i-propyl, cyclopropyl , cyclobutyl, cyclopentyl, cyclohexyl or phenyl, A38 means hydrogen, fluorine, chlorine, bromine, means methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i- • propoxy, methylthio, ethylthio, n- or i-propylthio substituted respectively by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, or by cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl respectively substituted, optionally by cyano, by fluorine, by chloro, by methyl or by ethyl, and
A39 means hydrogen, means methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy substituted, where appropriate, by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, or means cyc. clopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl respectively substituted, where appropriate, by cyano, by fluorine, by chlorine, by methyl or by ethyl. The object of the invention is preferably also the salts of lithium, sodium, potassium, magnesium, calcium, ammonium, alkyl-ammonium with 1 to 4 carbon atoms, di- (alkyl with 1 to 4 atoms carbon) -ammonium, tri- (C 1 -C 4) alkyl- ammonium, tetra- (C 1 -C 4) alkyl- ammonium, tri- (C 1 -C 4) 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). The definitions of the remains given above in a general manner and in the preferred ranges are valid both for the final products of the formula (I) and also correspondingly for the starting products or for the intermediate products ne-
respectively for obtaining. The definitions of the remains can be combined arbitrarily with each other, that is to say even between the indicated intervals. If, for example, 5,7-dimethyl-1,2,4-triazolo [1, 5-a] pyrimidine-2-sulfochloride and 2-aminophenol are used as starting materials, the development of the reaction in the process according to the invention by means of the following formula scheme.
The triazoloazinsulfonyl chlorides to be used as starting materials in the process according to the invention for the preparation of the compounds of the formula (I) are generally defined by the formula (II). In the formula (II), Q1, Q2, R1 and R2 preferably have those meanings which have already been mentioned above in a preferred manner for Q1, 2, R1 and R2 in relation to the description of the compounds of the formula (I ) according to the invention. The starting materials of the formula (II) are known and / or can be prepared according to processes known per se (cf. EP 142152, EP 244847, EP 375076,
). The amino (hetero) arenos to be used as starting materials in addition in the process according to the invention are generally defined by means of the formula (III). In the formula (III), Ar preferably has that meaning which has already been mentioned above preferably for Ar in relation to the description of the compounds of the formula (I) according to the invention. The starting materials of the formula (III) are known and / or can be prepared by processes known per se (cf. EP 142152, EP 244847, EP 375076, US 4605433, US 5163995, WO 89/10368). Suitable reaction aids for the process according to the invention are, in general, the usual inorganic or organic bases or
Acid acceptors They preferentially belong to the alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as, for example, sodium, potassium or calcium acetate, lithium amide. , sodium, potassium or calcium, sodium, potassium or calcium carbonate, sodium, potassium or calcium bicarbonate, lithium, sodium, potassium or calcium hydride, lithium hydroxide, sodium hydroxide, of potassium or calcium, methanolate, ethanolate, n- or i-propanolate, n- i-, s-
or sodium or potassium t-butanolate; also basic organic nitrogenous compounds, such as for example trimethylamine, triethylamine, tripropylamine, tri-butylamine, ethyldiisopropylamine, N, N-dimethyl-cyclohexyl-amine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-di-methyl-aniline, N , N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2, 4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl -pyridine, 5-ethyl-2-methyl-pi-ridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-diazabicyclo [2, 2, 2] -octane (DABCO), 1,5-diazabicyclo [4, 3, 0] -non-5-ene (DBN), or 1, 8-diazabicyclo [5, 4, 0] -undec-7-ene (DBU). Suitable diluents for carrying out the process according to the invention are, in particular, inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic halogenated hydrocarbons, such as, for example, benzene, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride, ethers. such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, or ethylene glycol dimethyl or diethyl ether; ketones, such as acetone, butanone, or methyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile or butyronitrile; amides, such as N, N-dimethylformamide,
N, N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrro-lidone or hexamethylphosphorotriamide; esters such as methyl acetate or ethyl acetate; sulfoxides, such as dimethylsulfoxide; alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water. The reaction temperatures in carrying out the process according to the invention can vary within wide limits. In general, work is carried out at temperatures between 0 ° C and 100 ° C, preferably between 10 ° C and 60 ° C. The process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under a higher pressure or at a lower pressure, generally between 0.1 bar and 10 bar. For carrying out the process according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess, the reaction is generally carried out in a suitable diluent in the presence of an auxiliary agent of the reaction and the reaction mixture is stirred.
in general for several hours at the necessary temperature. The preparation is carried out according to usual methods (see the preparation examples). The active compounds according to the invention of the formula (I) can be used as defoliants, desiccants, agents for removing weeds and, especially, for destroying weeds. By weeds, in the broadest sense, we must understand the plants that grow in places where they are unwanted. The fact that the products 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: Dicotyledonous bad herbs of the kinds; Sinapis, Le-pidium, Galium, Stellaria, Matricaria, Anthe is, Galin-rope, Chenopodiu, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa , Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum. Dicotyledonous crops of the following classes: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassi-
ca, Lactuca, Cucumis and Cucurbita. Bad monocotyledonous herbs of the kinds; Echino-chloa, Setaria, Panicu, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Oats, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera. Cultures of monocotyledonous classes: Oryza, Zea, Triticum, Hordeum, Avena, Sécale, Sorghum, Panicum, Saccharu, Ananas, Asparagus, Allium. The use of the active compounds according to the invention is, however, not limited in any way to these classes, but extends in the same way also to other plants. The compounds according to the invention are suitable, depending on the concentration, for combating completely the weeds, for example, in industrial and road installations and on roads and squares, with and without tree growth. Likewise, the compounds can be used to control weeds in permanent crops, for example, in forest installations, ornamental trees, fruit trees, vineyards, citrus trees, walnut trees, bananas, coffee, tea, from the rubber tree, from oil palms, from cocoa, from berries and hops, in ornamental paths
and sports and surfaces for meadows and to control weeds selectively in the annual crops. The compounds according to the invention of the formula (I) are especially suitable for the selective fight against monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous cultures both in the pre-emergence procedure and in the post-emergence procedure. The active compounds of the formula (I) according to the invention also have a potent microbicidal effect and can be used in practice for the control of undesired microorganisms. The active products are also suitable for use as fungicidal and bactericidal agents. Fungicidal agents in the protection of plants are used to fight against plasmodium-romicetes, oomycetes, chytridiomycetes, zygomycetes, as-comycetes, basidiomycetes, deuteromycetes. Bactericidal agents are used in the protection of plants for the control of pseudomonaceae, rhizobiaceae, enterobacteriaceae, corinabacteriaceae and streptomycetaceae. Some disease pathogens can be cited by way of example, but not by way of limitation.
fungal and bacterial substances that fall within the general definitions listed above: types of xanthomonas, such as for example Xanthomonas campestris pv. oryzae; pseudomonas types, such as, for example, Pseudomonas syringae pv. lachry ans; types of erwinia, such as for example Erwinia amylovora; types of pitium, such as for example Pythium ultimun; phytophthora types, such as for example Phytophthora infestans; pseudoperonospora types, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis; types of plasmopara, such as for example Plasmopara viticola; types of bremia, such as for example Bremia lactucae; types of peronospora, such as, for example, Peronospora pisi or P. brassicae; types of erisife, such as for example Erysiphe graminis; types of sfaeroteca, such as for example Sphaerotheca fuliginea; types of podosfaera, such as for example Podosphaera leucotricha; types of venturia, such as Venturia inae-qualis; Pyrenophora species, such as, for example, Pyreno-phora teres or P. graminea (conideas form: Drechslera, Syn: Helminthosporium); types of cocliobolus, such as for example Cochliobolus sativus (conidia form, Drechslera, Syn: Helminthosporium); types of uromices, such as, for example, Uromyces appendiculatus; types of pucinia, such as for example Puccinia recondita; types
of sclerotinia, such as for example Sclerotinia sclero- tumum; types of tilletia, such as for example Tilletia caries; types of ustylago, such as, for example, Ustilago nuda or Ustilago avenae; types of pelicularia, such as 5 for example Pellicularia sasa ii; blasting types, such as, for example, Pyricularia oryzae; Fusarium types, such as, for example, Fusarium culmorum; Botrytis types, such as, for example, Botrytis cinerea; Septoria types, such as, for example, Septoria nodorum; types of? k 10 leptosphaeria, such as for example Leptosphaeria nodorum; types of cercospora, such as for example Cercospora canescens; alternating types, such as, for example, Alternaria brassicae; types of pseudocercosporela, such as, for example, Pseudocercosporella herpotrichoides. 15 Good partial compatibility with plants
From the active products to the concentrations necessary for the fight against plant diseases, it allows a treatment of the aerial parts of the plants, of seedlings and seeds and of the soil. In this case, the active compounds according to the invention can be used, with good success, for combating the diseases of fruit tree and vegetable plantations, such as, for example, against the types of Podosphaera and Sphaerotheca, and for the fight against rice diseases,
such as, for example, against Pyricularia oryzae. The active compounds of the formula (I) according to the invention are suitable, to a certain extent, for the control of animal pests, preferably against arthropods and nematodes, especially insects and arachnids, which occur in agriculture, in forestry, for protection of stored products and materials as well as in the hygiene sector. They are active against normally sensitive and resistant species as well as against all or some of the stages of development. The plagues cited above belong: from the class of the isopods, for example, Oniscus asellus Armadillidium vulgare and Porcellio scaber; of the class of the diplópodos, for example, Blaniulus guttulatus; from the class of the chilopoda, for example, Geophilus carpopha-gus and Scutigera spec .; from the class of the syphilis, for example, Scutigerella immaculata; from the class of ti-saurians, for example, Lepisma saccharina; from the class of springtails, for example, Onychiurus armatus; of the class of the orthopterans, for example, Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp. , Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria; from the class of dermápteros, for example, Forfícula auricularia; from the class of loe
Isoptera, for example, Reticulitermes spp .; from the class of anophides, for example, Pediculus humanus corpo-ris, Haematopinus spp., and Linognathus spp .; from the class of the malophagous, for example, Trichodectes spp. and Dama-linea spp .; of the Thysanoptera class, for example, Hercinothrips femoralis and Thrips tabaci; of the class of the heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp .; from the class of Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Tria-leurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cruptomyzus ribis, Aphis fabae, Aphis pomi, Erio-soma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp. , Pemphigus spp., Phorodon humuli, Phyllo-xera vastatrix, Rhopalosiphum padi, Empoasca spp. , Eus-celis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp .; from the class of Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hypono-meuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp. , Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp. , Euxoa spp., Feltia spp., Earias insulana, Heliothis spp.,
Spodoptera exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubi-lalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudos- pretella, Cacoecia podana, Capua reticule, Choristoneura fumiferana, Clysia ambiguella, Homona magnánima and Tortrix viridana; from the class of coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Bruchidius obtectus, Hylotrupes bajulus, Age-lastica alni, Leptinotarsa decemlineata, Phaedon cochlea-riae, Diabrotica spp. , Psylliodes chrysocephala, Epilach-na varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp. , Sitophilus spp. , Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp. , Niptus hololeucus, Gibbium psylloidee, Tribolium spp. , Tenebrio molitor, Agriotes spp. , Conoderus spp. , Melolontha melolontha, Amphimallon solstitialis and Coselytra zealandica; of the Hymenoptera class, for example, Diprion spp., Hoplocampa spp. , Lasius spp., Monomorium pharaonis, Vespa spp. from the class of dipterans, for example, Aedes spp., Anopheles spp., Culex spp. , Drosophila melanogaster, Musca spp. , Fannia spp. ,
Calliphora erythrocephala, Lucilia spp. , Chrysomyia spp. , Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Sto-moxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp. , Bibio hortulanus, Oscinella frit, Phorbia spp. , Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa; from the class of siphonaptera, for example, Xenopsylla cheopis, Ceratophyllus spp.; from the class of arachnids, for example Scorpio maurus, Lac-trodectus mactans; of the mite class, for example Acarus siró, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp. , Ixodes spp. , Psoroptes spp. , Chorioptes spp. , Sar-coptes spp., Tarsonemus spp. , Bryobia praetiosa, Panony-chus spp. , Tetranychus spp. Plant parasitic nematodes include, for example, Pratylenchus spp., Radopholus spp., Ditylenchus spp., Tylenchulus spp., Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp. , Longidorus spp., Xiphinema spp., Trichodorus spp., Tylenchus spp., Helicotylenchus spp., Rotylenchus spp. , Tylenchulus spp. In this case, the active compounds according to the invention can be used with good success, for example against butterfly caterpillars such as, for example, against Plutella maculipennis.
The active ingredients can be converted 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 product active, as well as micro-encapsulated in polymer materials. These formulations are prepared in known manner, for example, by mixing the active products with extender materials, that is, with liquid solvents and / or solid diluents, if appropriate, using surfactants, that is, emulsifiers and / or dispersants and / or foam generating means. When using water as a filler, it is also possible, for example, to use organic solvents as auxiliary solvents. Particularly suitable solvents are: aromatic hydrocarbons, such as xylene, toluene, or alkyl naphthalenes, 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 petroleum, alcohols, such as butanol, or glycol, as well as their esters and ethers, ketones, such
such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone, strongly 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 earth and synthetic molten minerals, such as highly dispersed silicic acid. , aluminum oxide and silicates; as solid excipients for granulates are considered: for example broken and fractionated natural minerals such as calcite, marble, pumice, sepiolite, dolomite, as well as synthetic granules of inorganic and organic flours, as well as granulates of organic materials, such as sawdust, coconut husks, corn ears and tobacco stems; as emulsifiers and / or foam generators are considered: for example nonionic and anionic emulsifiers, such as esters of polyoxyethylenated fatty acids, ethers of polyoxyethylenated fatty alcohols, for example, alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulphonates, as well as the products of albumin hydrolysis; as dispersants
they come into consideration: for example, sulphite residual liquors of lignin and methylcellulose. Adhesives such as carboxymethylcellulose, natural and synthetic polymers powdery, granulated or in the form of latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cefaliña 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, Prussian blue, and organic dyes, such as alizarin dyes, azo dyes, and metal phthalocyanine dyes and trace nutrients, such as sodium salts, may be employed. iron, 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% by weight. The active compounds according to the invention can be used as such or in their formulations also for combating weeds in admixture with known herbicides, ready-to-use preparations or tank mixtures being possible. For mixtures, the herbi-
Known acids such as, for example, anuides, such as for example Diflufenican and Propanil; arylcarboxylic acids, such as dichloropoicolinic acid, Dicamba and Picloram; aryloxyalkanoic acids, such as for example 2,4 D, 2,4 DB, 2,4 DP, Fluroxypyr, MCPA, MCPP and Triclopyr; esters of the aryloxy-phenoxy-alkanoic acids, such as Diclofop-methyl, Fenoxaprop-ethyl, Fluazifop-butyl, Haloxyfop-methyl, and Quizalofop-ethyl; Azinone, such as, for example, Chloridazon and Norflurazon; carbamates such as for example Chlorpropham, Desmedi-pha, Phenmedipham and Propham; chloroacetanilide, such as, for example, Alachlor, Acetochior, Butachlor, Metaza-chlor, Metolachlor, Pretilachlor and Propachlor; dinitro-aniline such as for example Oryzalin, Pendimethalin and Trifluralin; diphenylether, such as for example Aci-fluorfen, Bifenox, Fluoroglycofen, Fomesafen, Halosafen, Lactofen and Oxyfluorfen; ureas such as for example Chlortoluron, Diuron, Fluometuron, Isoproturon, Linuron and Methabenzthiazuron; hydroxylamines such as, for example, Alloxydim, Clethodim, Cycloxydim, Sethoxydim and Tral-koxydim; imidazolinones, such as, for example, Imazethapyr, Imazamethabenz, Imazapyr and Imazaquin; nitriles, such as, for example, Bromoxynil, Dichlobenil and Ioxynil; oxyacetamides such as for example Mefenacet; sulphonylureas, such as for example Amidosulfuron, Ben-
sulfuron-methyl, Chlorimuron-ethyl, Chlorsulfuron, Cino-sulfuron, Metsulfuron-ethyl, Nicosulfuron, Primisulfu-ron, Pyrazosulfuron-ethyl, Thifensulfuron-methyl, Tria-sulfuron and Tribenuron-methyl; thiolcarbamates, such as for example Butylate, Cycloate, Diallate, EPTC, Espro-carb, Molinate, Prosulfocarb, Thiobencarb and Triallate; triazines, such as for example Atrazin, Cyanazin, Si-mazin, Simetryne, Terbutryne and Terbutylazin; triazinones, such as, for example, Hexazinon, Metamitron and Metribu-zin; others such as for example Aminotriazole, Benfure-sate, Bentazone, Cinmethylin, Clomazone, Clopyralid, Di-fenzoquat, Dithiopyr, Ethofumesate, Fluorochloridone, Glufosinate, Glyphosate, Isoxaben, Pyridate, Uinchlorac, Quin erac, Sulphosate and Tridiphane. A mixture with other known active compounds is also possible, such as herbicides, fungicides, insecticides, acaricides, nematicides, protective substances against ingestion by birds, nutrient substances of the plants and means for improving the structure of the soil. The active compounds can be used as such, in the form of their formulations or in the forms of application prepared therefrom by further dilutions, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules.
sides. Its use is carried out in the usual way for example by means of irrigation, 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 planting. The amount used of the active products can vary within a wide range. This depends 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 production and use of the active compounds according to the invention can be seen by the following axes. Examples of obtaining: Example 1.
A mixture consisting of 2.1 g (10 mmol) of 2-methylthio-6-n-butyroyl-aniline, 2.5 g (10 mmol) of 5,7-dimethyl-1,2,4-triazolo is stirred. l, 5-a] pyrimidin-2-
sulfochloride and 30 ml of pyridine approximately during
hours at room temperature (approximately 20 ° C). The pyridine is then carefully removed by vacuum distillation of the water tube, the residue is taken up in 100 ml of methylene chloride and washed twice with 2N hydrochloric acid and with water, dried over magnesium sulfate and washed with water. filter. The filtrate is concentrated by evaporation under vacuum of the water pump, the amorphous residue is crystallized by treatment with ethanol and the product is isolated by suction filtration. 2.8 g (67% of theory) of the 5,7-dimethyl-N- (2-methylthio-6-n-butyroylphenyl) -1,2,4-triazole [1,5-a] are obtained. ] pyrimidine-2-sulfonamide with a melting point of 138 ° C. Example 2
3.2 g (7.5 mmol) of 5,7-dimethyl-N- (2-methylthio-6-n-butyroyl-phenyl) -1,2,4-triazolo [1, 5-a] - are placed. pyrimidine-2-sulfonamide in 60 ml of chloroform and the solution is combined with 1.8 g of 3-chloroperbenzoic (at 70 ° C).
%). The reaction mixture is then stirred for about 60 minutes at room temperature ^ t (about 20 ° C) and then concentrated by evaporation under vacuum of the water tube. The residue is digested with 40 ml of ethanol and the crystalline product obtained is isolated by suction filtration. 2.3 g (70% of theory) of 5,7-di-methyl-N- (2-methylsulfinyl-6-n-butyroyl-phenyl) -1,2,4-triazolo [1, 5 a] pyrimidine-2-sulfonamide with a melting point of 255 ° C (with decomposition). Example 3
2.1 g (5 mmol) of 5,7-dimethyl-N- (2-methylthio-6-n-butyroyl-phenyl) -1,2,4-triazolo- [1,5-a] pyridine are placed. rimidin-2-sulfonamide in 50 ml of chloroform and the solution is combined with 2.8 g of 3-chloroperbenzoic acid (70%). The reaction mixture is then stirred for about 2 hours at room temperature (at about 20 ° C) and then concentrated by evaporation under vacuum of the water tube. He
The residue is digested with 30 ml of ethanol and the product
obtained crystalline is isolated by suction filtration. 2.0 g (89% of theory) of 5,7-dimethyl-n- (2-methylsulfonyl-6-n-butyroyl-phenyl) -1,2,4-triazolo [1, 5-a] are obtained. pyrimidin-2-sulfonamide with a melting point of 236 ° C (with decomposition). In a manner analogous to that of the preparation examples 1 to 3 and according to the general description of the preparation process according to the invention, the compounds of the formula (I) indicated in Table 1 below can also be prepared, for example.
Table i: Examples of compounds of the formula (I)
Table l (Continued)
T bla l (Continued)
Table i (Continued)
Table 1 (Continued)
Table l (Continued)
Table 1 (Continued)
Table 1 (Continued)
Table 1 (Continued)
Table 1 (Continued)
Table 1 (Continuation i
Table 1 (Continued)
Table 1 (continued)
Table 1 (Continued)
Table i (Continued)
Table i (Continued)
Table i (Continued)
Table l (Continued)
Table l (Continued)
Table 1 (Continued)
Table i (Continued)
Table 1 (Continued)
Table i (Continued)
Table 1 (Continued)
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 and after 24 hours the preparation of the active product is sprayed on the spot - in such a way that the desired quantity of active product per unit area is respectively applied. The concentration of the sprayable broth will be chosen in such a way that the desired amount of active product is applied in each case per 1000 liters of water / ha. After three weeks the degree of damage of the plants is evaluated in% damage compared to the development of the untreated control. They mean: 0% = no effect (same as untreated controls). 100% = total destruction.
In this test they show, for example, the compounds according to the preparation examples 4, 5, 6, 13, 14, 17, 18, 19, 22, 23, 25, 34, 35, 38, 39, 43, 60, 63 , 73, 74, 75, 76, 77, 82, 84, 85, 104, 115, 118 and 121, with a partially good compatibility with crop plants, such as, for example, soybeans and cotton, a potent effect against weeds (see the following tables corresponding to example A).
•
Table A: Pre-sprout / greenhouse test 1) Compounds according to Quantity Wheat Alope- Bromus Echino-Lolium Galium Matri- Sola- the example of ob- used curus chloa caria num tention n-¡(q ai. / Ha) 13 250 5 100 - 100 80 100 100 100 14 125 - 95 95 100 90 70 100 100
2) Compound according to Quantity Wheat Alope- Cyperus Digi-Echino-Galium Matri- Sola- the example of ob- employed curus taria chloa caria num tention na (q ai. / Ha) 43 125 10 100 100 100 100 100 100 100
3) Compound according to Quantity Wheat Alope- Cyperus Digi- Galium Galin-Matri- Sola- the example of ob- used curus taria soga caria num tention na (q ai. / Ha) 60 500 20 95 100 85 95 95 95 95
4) Compounds according to Quantity Soybean Bromus Echino-Loliuim Poa Galium Galin-Matri- Sola- the example of ob- employee chloa soga caria num tention n (q ai. / Ha) 75 1,000 10 80 90 95 95 95 100 95 95 5) Compound according to Quantity Something- Alope- Digi-Echino-Poa Galin- Matri- Sola- the example of ob- employed don curus taria chloa soga caria mum tention na (q ai. / Ha) 104 250 0 80 90 .80 80 90 95 90
6) Compound according to Quantity Wheat Soy Digi Poa Galin- MatriSola- the example of ob- used taria soga caria um tention na (q ai. / Ha) 115 100 0 0 95 100 95 90 121 125 70 95 95 90
•
7) Compound according to Amount Alo-Bromus Cyperus Echino-Lolim Galium Matri- Sola- the example of ob cessed pecurus chloa caria num tion na (g ai. / Ha) 76 500 100 100 100 100 100 100 100 100 8) Compound according to Quantity Alo- Cype- Digi-Echino-Galium Galin-Matri- Sola- the example of obempleada pecurus rus taria chloa noga caria num tention nd (q ai. / ha) 73 250 - 95 95 95 95 95 95 95 74 250 80 - 95 90 90 100 95 95
9) Compound according to Quantity Alo- CypeEchino- Galium Galin- Matri- Sola1 the example of ob- employee pecurus rus chloa rope carla num 8 1 tension ns (cr ai. / Ha) 5 125 95 90 95 95 95 95 90 4 125 90 95 90 90 95 95 90 85 125 90 90 90 90 95 95 90 84 250 80 95 70 90 95 95 95 19 250 80 100 95 - 95 95 - 6 500 95 90 90 95 95 95 95 34 250 99 95 90 100 - 100 100 35 250 95 - 95 95 100 95 95 22 250 80 - 95 100 100 95 95 23 250 - - 95 100 100 95 - 25 500 80 80 100 100 - 100 100 118 250 80 95 95 90 95 95 95
) Compound according to Quantity Alo- Digi-Echino-Galium Matri- Sola- the example of obempleada peourus taria chloa caria num tention na (q ai. / Ha) 82 500 95 95 100 100 100 100 63 125 100 95 100 100 100 100 11) Compound according to Quantity AloDigi-Echino-Poa Galium Galin-Matri- Sola- the example of obe-tipleada pecurus taria chloa rope caria num tention na (g ai. / Ha) 17 250 95 95 - 95 95 95 95 95 18 250 90 90 95 90 95 100 100 95 i Ti 12) Compound according to Quantity Alo-Galium Matri- SolaI the example of ob- employed pecurus caria num ention na (q ai. / Ha) 38 500 80 100 100 95 39 500 80 100 100 100 13) Compound by quantity Cyperus Echino-Lolium Galium M triSolael example of ob- employee chloa carla numtion na (g ai. / Ha) 77 500 95 90 80 95 100 95
Example B: Post-outbreak trial. Solvent: 5 parts by weight of acetone. Emulsifier: 1 Part by weight of alkylaryl polyglycol-5 ether. To obtain a suitable preparation of active compound, 1 part by weight of the active compound is mixed with the indicated amount of solvent, the indicated amount of emulsifier is added and the concentration is diluted with water to the desired concentration. With the preparation of the active product, test plants are sprayed, which have a height of 5-15 cm, so that in each case the desired quantities of active compound per unit of surface are applied. The concentration of the sprayable broths is chosen in such a way that they are applied in 1000 1 of water / ha
^ the quantities of active product desired in each case. After three weeks, the degree of damage to the plants is evaluated in% damage compared to the development of the untreated controls. They mean: 0% = no effect (like untreated controls). 100% = total destruction. In this test they show, for example, the co-positions according to the obtaining examples 6, 17, 18, 19,
22, 60, 63, 73, 76, 77, 82, 84, 118 and 121, with completely good compatibility with crop plants, such as, for example, wheat, a potent effect against weeds (see next tables corresponding to example B).
Table B: Post-emergence / greenhouse trial
1) Compounds according to Amount Wheat Abutilon Datura Ipomoea Matri- Sola- Xan- the example of ob- used caria num thiu tention na (q ai. / Ha) 84 125 10 - 90 90 80 90 70 19 1000 - 95 90 95 95 95 100 6 125 10 95 90 80 90 95 70. 22 500 5 - 4 100 95 95 100 90"NJ 100 i 118 250 10 95 95 95 90 100 100 73 125 20 95 95 90 100 95 100 60 125 5 90 90 80 - 90 70 121 500 5 - 60 100 70 95 95 76 500 20 95 70 90 95 95 100 77 500 - 95 - 80 100 95 100 17 30 10 95 90 90 95 90 95.
•
2) Compound according to Quantity Wheat Lolium Sorghum Datura Ipo- Matri- Sola- Xan- the example of employed moea caria num thium obtaining na (q ai. / Ha) 82 500 95 95 100 100 100 100 100 18 125 10 80 80 90 90 100 90 95
3) Compound according to Quantity Alope- Lolium Sorghum Datura Ipo- Matri- Sola- Xan- i the example of used curus moea caria num thium «*» obtaining na (g ai. / Ha) 63 125 90 80 95 95 95 95 100 95
Example C: Test with Sphaerotheca (cucumber) / protector. Solvent: 4.7 parts by weight of acetone. Emulsifier: 0.3 Parts by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active compound, 1 part by weight of the active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test the protective activity, young plants are sprayed with the preparation of the active compound. After drying the coating formed by spray, the plants are sprayed with conids of the fungus Sphaerole theca fuliginea. The plants are then placed at 23 to 24 ° C and at a relative humidity of about 75% in the greenhouse. The evaluation is carried out 10 days after the inoculation. In this test, for example, the compounds according to Preparation Examples 4, 5, 19 and 85 show a potent activity (see table C below).
Table C: Test with Sphaerotheca (cucumber) / protector.
Example D: Test with Podosphaera (apple tree) / protector. Solvent: 4.7 parts by weight of asketone. Emulsifier: 0.3 Parts by weight of alkylaryl polyglycol ether. To obtain a suitable preparation of active ingredients, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration. To test the protective effect, young plants are sprayed, until they drip, with the preparation of the active compound. After drying the sprayed coating the plants are inoculated by powdering with conidia of the pathogen of the apple tree powdery mildew Podosphaera leucotricha. The plants are then placed in the greenhouse at 23 ° C and approximately 70% relative humidity. The evaluation is carried out 10 days after the inoculation. In this test, for example, the compounds according to Preparation Examples 4, 5, 19 and 85 show a potent activity (see Table D below).
Example E: Test with Plutella Solvent: 7 parts by weight of dimethylformamide. Emulsifier: 1 Part by weight of alkylaryl polyglycol ether. To obtain a convenient preparation of the active compound, 1 part by weight of the active compound is mixed with the indicated amount of solvent and with the indicated amount of emulsifier and the concentrate is diluted with water to the desired concentration.
• Cabbage leaves (Brassica olerácea) are treated by being dipped into the preparation of the active product of the desired concentration and covered with caterpillars of the cabbage moth (Plutella maculipennis), while
as long as the leaves are still wet. At the end of the desired time, the gra¬
•% destruction in%. In this case 100% means that all caterpillars were destroyed; 0% means that no caterpillar was destroyed. In this test, for example, the compounds of the preparation examples 21, 23 and 36 show a potent activity (see table E below)
It is noted that in relation to this date,
The best method known by the applicant to carry out the aforementioned invention is that which is clear from the present description of the invention. Having described the invention as above, the content of the following is claimed as property:
Claims (7)
1.- Triazoloazinsulfone substituted idas of the general formula (I) characterized in that Q1 signifies nitrogen or a grouping CH-, Q2 signifies nitrogen or a grouping CH-, R1 signifies hydrogen, halogen or means alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, alkylamino with 1 to 4 carbon atoms or di (alkyl with 1 to 4 carbon atoms) -amino substituted, where appropriate, by hydroxy, by halogen or by alkoxy with 1 to 4 carbon atoms, Ro si.gni.fi.ca hi.drógeno, halogen or signi.fi.ca alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, alkylamino with 1 to 4 carbon atoms or di- (C 1 -C 4) -amino substituted by halogen, respectively, and Ar means 4-cyano-2,5-difluoro-phenyl, 2,6-dimethoxy-fe - nyl, 2-bromo-3-trifluoromethyl-phenyl, 2-bromo-5-trifluoromethyl-phenyl, 4-bromo-2,6-dimethyl-phenyl, 6-chloro- ro-pyridin-3-yl-methyl or one of the following cyclic groupings (hetero) with 5 or 6 members:, where m means respectively the numbers 1 or 2, n means respectively the numbers 0, 1 or 2, A1 means alkyl having 1 to 4 carbon atoms subsituted, if appropriate, by cyano, by halogen or by alkoxy with 1 to 4. carbon atoms or means cycloalkyl with 3 to 6 carbon atoms, optionally substituted by cyano, halogen or by alkyl with 4 carbon atoms, 10 A2 means alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 atoms of carbon, alkylthio having 1 to 4 carbon atoms, alkylsulfinyl having 1 to 4 carbon atoms or alkylsulfonyl having 1 to 4 carbon atoms, substituted, if appropriate, by halogen, respectively) R3 means alkyl having 1 to 4 carbon atoms carbon substi¬ • optionally cyano, halogen or alkoxy with 1 to 4 carbon atoms, A4 means alkyl with 1 to 4 carbon atoms, optionally substituted by cyano, halogen or alkoxy with 1 to 4 carbon atoms, A5 means alkyl having 2 to 4 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, means alkenyl having 2 to 4 carbon atoms, optionally substituted by halogen or means cycloalkyl having 3 to 6 carbon atoms-alkyl having 1 to 4 carbon atoms, optionally substituted by cyano, halogen or alkyl having 1 to 4 carbon atoms, A6 means halogen or means alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms or alkenyloxy with 2 to 4 carbon atoms substituted, where appropriate, by halogen, A7 means alkyl with 1 to 4 carbon atoms substituted per cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, A8 means cyano, nitro or alkyl with 1 to 4 carbon atoms, optionally substituted by halogen, A9 means cyano, halogen or means alkyl with 1 to 4 atoms of carbon optionally substituted by halogen, A10 means alkyl having 1 to 4 carbon atoms, optionally substituted by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms or by cycloalkyl with 3 to 6 carbon atoms optionally substituted by cyano, by halogen or by alkyl with 1 to 4 carbon atoms, A11 means hydrogen or means alkyl with 1 to 4 carbon atoms, alkyl-carbonyl with 1 to 4 atoms of carbon, alkoxycarbonyl with 1 to 4 carbon atoms or alkylsulfonyl with 1 to 4 carbon atoms substituted, where appropriate, by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms, A12 means hydrogen, cyano, halogen or means alkyl having 1 to 4 carbon atoms, optionally substituted by halogen, A13 means cyano, carbamoyl, 5,6-dihydro-i, 4,2-dioxazin-3-yl, halogen, alkyl with 1 to 4. carbon atoms, alkylcarbonyl with 1 to 4 carbon atoms or alkoxycarbonyl with 1 to 4 carbon atoms, A14 means hydrogen, meaning cyano, carbamoyl, halogen, alkyl with 1 to 4 carbon atoms, alkylcarbonyl with 1 to 4 carbon atoms. carbon atoms or alkoxycarbonyl having 1 to 4 carbon atoms, A15 means hydrogen, meaning cyano, carbamoyl, halogen, alkyl with 1 to 4 carbon atoms, alkylcarbonyl with 1 to 4 carbon atoms or alkoxycarbonyl with 1 to 4 carbon atoms or together with A14 means a benzo-ringed ring, A16 means hydrogen, cyano, halogen or means alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 atoms of carbon, alkylsulfinyl with 1 to 4 carbon atoms, or alkylsulfonyl having 1 to 4 carbon atoms substituted, if appropriate, by halogen, A17 means hydrogen, cyano, halogen or means alkyl with 1 to 4 carbon atoms substituted in each case by halogen, A18 means hydrogen, cyano, halogen or means alkyl having 1 to 4 carbon atoms, optionally substituted by halogen, A 19 means hydrogen or alkyl having 1 to 4 carbon atoms, A 20 means alkyl having 1 to 4 carbon atoms or alkenyl having 2 to 4 carbon atoms, A21 means cyano, halogen, alkyl having 1 to 4 carbon atoms or haloalkyl with 1 to 4 carbon atoms, A22 means alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms, A23 means alkyl with 1 to 4 carbon atoms, A24 individually means alkyl having 1 to 4 carbon atoms or together with A23 means alkanediyl having 2 to 4 carbon atoms, A25 means cyano, halogen, alkyl having 1 to 4 carbon atoms or halogenalkyl having 1 to 4 carbon atoms, A26 means alkyl with 1 to 4 carbon atoms, A27 means cyano, halogen, alkyl having 1 to 4 carbon atoms, halogenoalkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or halogenalkoxy with 1 to 4 carbon atoms, A28 means hydrogen, difluoromethyl, alkylcarbonyl with 1 to 4 carbon atoms, alkoxycarbonyl with 1 to 4 carbon atoms, alkylsulfonyl with 1 to 4 carbon atoms, A29 means cyano, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms, A30 means hydrogen, alkyl with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms, A31 means hydrogen or alkyl with 1 to 4 carbon atoms, A32 means cyano, halogen, alkyl with 1 to 4 carbon atoms or halogenalkyl with 1 to 4 carbon atoms, A33 means hydrogen, alkyl with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms, A34 means hydrogen or alkyl with 1 to 4 carbon atoms , A35 means cyano, halogen, alkyl c on 1 to 4 carbon atoms or haloalkyl with 1 to 4 carbon atoms, A36 means hydrogen, alkyl having 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms or phenyl, • A37 means hydrogen, alkyl having 1 to 4 carbon atoms, cycloalkyl having 3 to 6 carbon atoms or phenyl, A38 means hydrogen, halogen, means alkyl having 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms or alkylthio having 1 to 4 carbon atoms subsituted respectively, if appropriate, by cyano, halogen or C 1 -C 4 -alkoxy, or C 3 -C 6 -cycloalkyl means, cycloalkyloxy with 3 to 6 carbon atoms or cycloalkyl with 3 to 6 carbon atoms-alkyl having 1 to 4 carbon atoms substituted respectively in case given by cyano, by halogen or by alkyl with 1 • at 4 carbon atoms, and A39 means hydrogen, means alkyl with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms respectively substituted, where appropriate, by cyano, by halogen or by alkoxy with 1 to 4 carbon atoms; carbon, or means cycloalkyl with 3 to 6 carbon atoms, cycloalkyloxy with 3 to 6 carbon atoms or cycloalkyl with 3 to 6 carbon atoms-alkyl having 25 to 4 carbon atoms, respectively substituted optionally by cyano, by halogen or by alkyl with 1 to 4 carbon atoms, as well as the salts of the compounds of the formula (I).
2. Compounds of the formula (I) according to claim 1, characterized in that in the same Q1 it means nitrogen or a group CH-, Q2 means nitrogen or a group CH-, R1 means hydrogen, fluorine, chlorine, bromine or means methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n-, or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino substituted respectively, where appropriate, fluorine, chlorine, methoxy or ethoxyR 2 means hydrogen, fluorine, chlorine, bromine or means methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n - or i-propylamino, dimethylamino, or diethylamino substituted, where appropriate, by fluorine, chlorine, methoxy or ethoxy, Ar means 4-cyano-2,5-difluoro-phenyl, 2,6-dimethoxy-phenyl , 2-bromo-3-trifluoromethyl-phenyl, 2-bromo-5-trifluoromethyl-phenyl, 4-bromo-2,6-dimethyl-phenyl, 6-chloro-pyridin-3-yl-methyl or one of the following groupings: where m means respectively the numbers 1 or 2, n means respectively the numbers 0, 1 or 2, A1 means methyl, ethyl, n- or i-propyl, substituted respectively by cyano, by fluorine, by chlorine, by bromine, by methoxy or by ethoxy or means cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl respectively substituted, where appropriate, by cyano, fluorine, chlorine, bromine, methyl or ethyl, A2 means methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulphinyl, n- or i-propylsulfinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl substituted, where appropriate, by fluorine, by chlorine or by bromine, A3 means methyl, ethyl, n- or i-propyl respectively substituted, if appropriate, by cyano, fluorine, chlorine or bromine, methoxy or ethoxy, A4 means methyl, ethyl, n- or i- propyl substituted, where appropriate, by cyano, by fluorine, by chlorine, by bromine, by methoxy or by ethoxy, A5 s denotes ethyl, n- or i-propyl, n-, i-, s- or t-butyl substituted respectively by cyano, by fluorine, by chlorine, by bromine, by methoxy or by ethoxy, means substituted propenyl or butenyl respec- tively, if applicable, by halogen, or cyclopropylmethyl, cyclobutyl ethyl, cyclopentylmethyl or cyclohexyl ethyl substituted, where appropriate, by cyano, by fluorine, by chlorine, by bromine, • for methyl or for ethyl, A6 means fluorine, chlorine, bromine or means methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, propenyl, butenyl, propenyloxy or butenyloxy substituted respectively given by fluorine or by chlorine, A7 means methyl, ethyl, n- or i-propyl substituted respectively by cyano, by fluorine, by chlorine, by bromine, by methoxy or by ethoxy, A8 means cyano, nitro or methyl, ethyl, n- or i-propyl substituted respectively by fluorine or by chlorine, respectively A9 means cyano, fluorine, chlorine or means methyl, eti¬ • I, n- or i-propyl substituted respectively by fluorine or chlorine, respectively, A10 means hydrogen, means methyl, ethyl, n- or i-propyl substituted respectively by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, or means cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl respectively substituted, where appropriate, by cyano, by fluorine, by chlorine, by methyl or by ethyl, A11 means hydrogen or means methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarboni¬ The methylsulfonyl, ethylsulfonyl, n- or i-propylsulphonyl substituted respectively by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, A12 means hydrogen, cyano, fluorine, chlorine, bromine or methyl. , ethyl, n- or i-propyl respectively substituted, if appropriate, by fluorine or by chlorine, A13 means cyano, carbamoyl, 5,6-dihydro-1,4,2-dioxazin-3-yl, fluorine, chlorine , bromine, methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, A14 means hydrogen, means cyano, carbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, • acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, A15 means hydrogen, means cyano, carbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl or together with A14 means a benzo-ringed grouping, A means hydrogen, cyano, fluorine, chlorine, bromine or means methyl, ethyl, n- or i-propyl, methoxy, etho- xi, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulphonyl, respectively substituted, if appropriate by fluorine or chlorineA17 means hydrogen, cyano, fluorine, chlorine, bromine or means methyl, ethyl, n- or i-propyl substituted, respectively, respectively by fluorine or chlorine, A18 means hydrogen, cyano, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl, respectively substituted, if appropriate, by fluorine or chlorine, A19 means hydrogen, methyl, ethyl, n- or i-propyl, A20 means methyl, ethyl, n- or i-propyl, or propenyl or butenyl, A21 means cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, or means trifluoromethyl, A22 means methyl, ethyl, n- or i-propyl, A23 means methyl, ethyl, n- or i-propyl, A24 individually means methyl, ethyl, n- or i-propyl or together with A23 means ethane-1,2-diyl (diethylene) or propane-1,3-diyl (trimethylene), A25 means cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, or means trifluoromethyl, A26 means methyl, ethyl, n- or i-propyl, A27 means cyano, fluorine, chlorine, br omo, methyl, ethyl, n- or i-propyl, or means trifluoromethyl, A28 means hydrogen, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylsulfonyl, ethylsulfonyl, n- or i- 5-propylsulfonyl, A29 means cyano, fluoro, chloro, bromo, methyl, ethyl, n- or i-propyl or means trifluoromethyl, A30 means hydrogen, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, | A31 means hydrogen or methyl, ethyl, n- or i-propyl, A32 means cyano, fluoro, chloro, bromo, methyl, ethyl, n- or i-propyl, or means trifluoromethyl, A33 means hydrogen, methyl, ethyl, n - or i-propyl, methoxy, ethoxy, n- or i-propoxy, A34 means hydrogen, methyl, ethyl, n- or i-propyl, A35 means cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, or means trifluoromethyl, A36 means hydrogen, methyl, ethyl, n- or i-propyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl, A37 means hydrogen, methyl, ethyl, n- or i-propyl, cyclopropyl , cyclobutyl, cyclopentyl, cyclohexyl or phenyl, A °° means hydrogen, fluorine, chlorine, bromine, means 25 methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i- propoxy, methylthio, ethylthio, n- or i-propylthio substituted, where appropriate, by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, or means cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclopentyl hexyloxy, cyclopropylmethyl, cyclobutyl ethyl, cyclopentylmethyl or cyclohexylmethyl substituted, where appropriate, by cyano, by fluorine, by chlorine, by methyl or by ethyl, and A39 means hydrogen, means methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy substituted, where appropriate, by cyano, by fluorine, by chlorine, by methoxy or by ethoxy, or by cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl substituted, where appropriate, by cyano, fluorine, chlorine, methyl or ethyl, and their lithium, sodium, potassium, magnesium, calcium, ammonium, alkyl-ammonium with 1 to 4 carbon atoms, di- (alkyl with 1 to 4 carbon atoms) -ammonium, tri (alkyl with 1 to 4 carbon atoms) ) -ammonium, tetra- (alkyl with 1 to 4 carbon atoms) -ammonium, tri- (alkyl with 1 to 4 carbon atoms) no) -sulfonium, cycloalkyl-ammonium with 5 or 6 carbon atoms and di- (C 1 -C 2 -alkyl) -benzyl-ammonium of the compounds of the formula (1).
3. Process for the preparation of substituted triazo-loazinsulfonamides of the formula (1) according to claim 1, characterized in that substituted triazoloazinsulfonyl chlorides of the general formula (II) are reacted wherein Q1, Q2, R1 and R2 have the meaning indicated in claim 1, with amino (hetero) arenos of the general formula (III) H2N-Ar (III) wherein Ar has the abovementioned meaning, if appropriate in the presence of an auxiliary agent of the reaction and, if appropriate, in the presence of a diluent, and, if appropriate, they are carried out in the compounds of the formula (I), obtained in this way, other reactions of transformation in the scope of the definition of the substituents previously indicated, according to usual methods.
4. Agents for the treatment of plants, characterized in that they have a content in at least one compound of the formula (I) or in one of its salts according to claim 1.
5.- Use of the compounds of the general formula ( I), or its salts according to claim 1, for combating the undesirable growth of plants, against undesirable microorganisms and / or against animal pests.
6. - Procedure for the fight against weeds, undesirable microorganisms and / or animal pests, characterized in that compounds of the general formula (I) or their salts, according to claim 1, are allowed to act on the weeds , on undesirable microorganisms or on animal pests or on their environment.
7. - Process for obtaining agents for the treatment of plants, characterized in that compounds of the general formula (I) or their salts, according to claim 1, are mixed with extenders and / or with surfactants. SUMMARY OF THE INVENTION The invention relates to new substituted triazoloazine sulfonamides of the formula (I) wherein Q1 signifies nitrogen or a grouping CH-, Q2 signifies nitrogen or a grouping CH-, R1 signifies hydrogen, halogen or means alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, alkylamino having 1 to 4 carbon atoms or di- (alkyl having 1 to 4 carbon atoms) amino substituted, where appropriate, by hydroxy, halogen or alkoxy with 1 to 4 carbon atoms, R2 means hydrogen, halogen, or means alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, alkylamino with 1 to 4 carbon atoms or di- (alkyl with 1) to 4 carbon atoms) -amino substituted respectively by halogen and Ar means 4-cyano-2,5-difluoro-phenyl, 2,6-dimethoxy-phenyl, 2-bromo-3-tri-fluoro-methyl- phenyl, 2-bromo-5-trifluoromethyl-phenyl, 6-chloro-pyridin-3-yl-methyl or means one of the groupings (hetero) cycl icos with 5 or 6 members cited in the description, as well as its salts, a process for obtaining the new compounds and their use as agents for the treatment of plants.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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DE19629144.5 | 1996-07-19 |
Publications (1)
Publication Number | Publication Date |
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MXPA99000641A true MXPA99000641A (en) | 1999-06-01 |
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