DD252113A5 - HERBICIDE MEDIUM - Google Patents
HERBICIDE MEDIUM Download PDFInfo
- Publication number
- DD252113A5 DD252113A5 DD86294528A DD29452886A DD252113A5 DD 252113 A5 DD252113 A5 DD 252113A5 DD 86294528 A DD86294528 A DD 86294528A DD 29452886 A DD29452886 A DD 29452886A DD 252113 A5 DD252113 A5 DD 252113A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- alkyl
- alkoxy
- halogen
- substituted
- phenyl
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title abstract description 15
- 239000004009 herbicide Substances 0.000 title description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 30
- 150000002367 halogens Chemical class 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- -1 phenylthio, phenylsulfinyl Chemical group 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 20
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 38
- 241000196324 Embryophyta Species 0.000 abstract description 30
- 239000000203 mixture Substances 0.000 abstract description 18
- 238000009472 formulation Methods 0.000 abstract description 7
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract description 3
- 125000004414 alkyl thio group Chemical group 0.000 abstract description 3
- 125000003302 alkenyloxy group Chemical group 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract description 2
- 241000269627 Amphiuma means Species 0.000 abstract 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 abstract 1
- 125000005133 alkynyloxy group Chemical group 0.000 abstract 1
- CEBXXEKPIIDJHL-UHFFFAOYSA-N alternariol Chemical compound O1C(=O)C2=C(O)C=C(O)C=C2C2=C1C=C(O)C=C2C CEBXXEKPIIDJHL-UHFFFAOYSA-N 0.000 abstract 1
- 230000009286 beneficial effect Effects 0.000 abstract 1
- 125000004966 cyanoalkyl group Chemical group 0.000 abstract 1
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 abstract 1
- 125000002071 phenylalkoxy group Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000004480 active ingredient Substances 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000011734 sodium Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000003921 oil Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- ULHHOGKLGFZMRZ-UHFFFAOYSA-N 2-(4-chloro-2-fluoro-5-methoxyphenyl)-3-hydroxy-4,5,6,7-tetrahydro-3h-isoindol-1-one Chemical compound C1=C(Cl)C(OC)=CC(N2C(C3=C(CCCC3)C2O)=O)=C1F ULHHOGKLGFZMRZ-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000013543 active substance Substances 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- PKUKHXKXLNTZKX-UHFFFAOYSA-N 3-chloro-2-(4-chloro-2-fluoro-5-methoxyphenyl)-4,5,6,7-tetrahydro-3h-isoindol-1-one Chemical compound C1=C(Cl)C(OC)=CC(N2C(C3=C(CCCC3)C2Cl)=O)=C1F PKUKHXKXLNTZKX-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000004495 emulsifiable concentrate Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 5
- 239000010695 polyglycol Substances 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000003408 phase transfer catalysis Methods 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- JVMZFLHKLVDXBL-UHFFFAOYSA-N 2-(4-chloro-2-fluoro-5-methoxyphenyl)-3-(diethylamino)-4,5,6,7-tetrahydro-3h-isoindol-1-one Chemical compound O=C1C(CCCC2)=C2C(N(CC)CC)N1C1=CC(OC)=C(Cl)C=C1F JVMZFLHKLVDXBL-UHFFFAOYSA-N 0.000 description 2
- IELXCBUUSRXWKD-UHFFFAOYSA-N 2-(4-chloro-2-fluoro-5-methoxyphenyl)-3-fluoro-4,5,6,7-tetrahydro-3h-isoindol-1-one Chemical compound C1=C(Cl)C(OC)=CC(N2C(C3=C(CCCC3)C2F)=O)=C1F IELXCBUUSRXWKD-UHFFFAOYSA-N 0.000 description 2
- OBFDOLPNJGOHCG-UHFFFAOYSA-N 2-(4-chloro-2-fluoro-5-methoxyphenyl)-3-phenylsulfanyl-4,5,6,7-tetrahydro-3h-isoindol-1-one Chemical compound C1=C(Cl)C(OC)=CC(N2C(C3=C(CCCC3)C2SC=2C=CC=CC=2)=O)=C1F OBFDOLPNJGOHCG-UHFFFAOYSA-N 0.000 description 2
- CMJUNAQINNWKAU-KTKRTIGZSA-N 2-[[(z)-2-oxononadec-10-enyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)CNCCS(O)(=O)=O CMJUNAQINNWKAU-KTKRTIGZSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 241000219146 Gossypium Species 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 235000021536 Sugar beet Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 241001148683 Zostera marina Species 0.000 description 2
- GTUKODJHMCTYFA-UHFFFAOYSA-N [2-(4-chloro-2-fluoro-5-methoxyphenyl)-3-oxo-4,5,6,7-tetrahydro-1h-isoindol-1-yl] acetate Chemical compound C1=C(Cl)C(OC)=CC(N2C(C3=C(CCCC3)C2OC(C)=O)=O)=C1F GTUKODJHMCTYFA-UHFFFAOYSA-N 0.000 description 2
- NJCBDFDIDRARPE-UHFFFAOYSA-N [2-(4-chloro-2-fluoro-5-methoxyphenyl)-3-oxo-4,5,6,7-tetrahydro-1h-isoindol-1-yl] methyl carbonate Chemical compound O=C1C(CCCC2)=C2C(OC(=O)OC)N1C1=CC(OC)=C(Cl)C=C1F NJCBDFDIDRARPE-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910001513 alkali metal bromide Inorganic materials 0.000 description 2
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 2
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 244000038559 crop plants Species 0.000 description 2
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- 239000002270 dispersing agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- ZUZMNZZQTIVJBX-UHFFFAOYSA-N ethyl 2-[4-[[2-(4-chloro-2-fluoro-5-methoxyphenyl)-3-oxo-4,5,6,7-tetrahydro-1h-isoindol-1-yl]oxy]phenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)OCC)=CC=C1OC1C(CCCC2)=C2C(=O)N1C1=CC(OC)=C(Cl)C=C1F ZUZMNZZQTIVJBX-UHFFFAOYSA-N 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
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- 239000007787 solid Substances 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
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- 238000009736 wetting Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- ZFWNZBXRODTRIC-UHFFFAOYSA-N 2,3,4,5,6,7-hexahydroisoindol-1-one Chemical compound C1CCCC2=C1C(=O)NC2 ZFWNZBXRODTRIC-UHFFFAOYSA-N 0.000 description 1
- BDOCBAWRJGGVDR-UHFFFAOYSA-N 2-(4-chloro-2-fluoro-5-methoxyphenyl)-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound C1=C(Cl)C(OC)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F BDOCBAWRJGGVDR-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- HMMBJOWWRLZEMI-UHFFFAOYSA-N 4,5,6,7-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CCCC2=C1C(=O)OC2=O HMMBJOWWRLZEMI-UHFFFAOYSA-N 0.000 description 1
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- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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- 102000007641 Trefoil Factors Human genes 0.000 description 1
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- KPQICJUYMAZQLO-UHFFFAOYSA-N [2-(4-chloro-2-fluoro-5-methoxyphenyl)-3-oxo-4,5,6,7-tetrahydro-1h-isoindol-1-yl] n-methoxycarbamate Chemical compound O=C1C(CCCC2)=C2C(OC(=O)NOC)N1C1=CC(OC)=C(Cl)C=C1F KPQICJUYMAZQLO-UHFFFAOYSA-N 0.000 description 1
- 230000006578 abscission Effects 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
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- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- ILYSHPJWNMPBPE-UHFFFAOYSA-N ethyl 2-(4-hydroxyphenoxy)propanoate Chemical compound CCOC(=O)C(C)OC1=CC=C(O)C=C1 ILYSHPJWNMPBPE-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 208000037824 growth disorder Diseases 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 230000008654 plant damage Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000036435 stunted growth Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
- A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/20—N-Aryl derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/50—Iso-indoles; Hydrogenated iso-indoles with oxygen and nitrogen atoms in positions 1 and 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
- C07F9/5728—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
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- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
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- Environmental Sciences (AREA)
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Abstract
Die Erfindung betrifft neue herbizide Mittel mit einem Gehalt von 2-Aryl-4,5,6,7-tetrahydroisoindolinonen fuer die Anwendung in der Landwirtschaft zur selektiven Unkrautbekaempfung in Nutzpflanzenkulturen mit vorteilhafter Wirkung gegen mono- und dikotyle Schadpflanzen. Erfindungsgemaess werden als Wirkstoff in den neuen herbiziden Mitteln Verbindungen der Formel angewandt, worin R1H oder Alkyl, R2Wasserstoff oder Halogen, R3Halogen, R4Hydroxy, Alkoxy, Alkoxyalkoxy, Cycloalkoxy, Alkenyloxy, Alkinyloxy, Alkylthio, Alkylsulfinyl, Alkylsulfonyl, NO2, CN, Halogen oder Cyanoalkyl, Phenoxy, Phenoxyalkyl, Phenylalkoxy, Phenylthio, Phenylsulfinyl, Phenylsulfonyl, AOH, SH, Halogen, CN u. a. bedeuten neben Formulierungshilfsmitteln. FormelThe invention relates to novel herbicidal compositions containing 2-aryl-4,5,6,7-tetrahydroisoindolinonen for use in agriculture for selective weed control in crops with beneficial effect against mono- and dicotyledonous harmful plants. According to the invention, the active compounds used in the novel herbicidal compositions are compounds of the formula in which R 1 is H or alkyl, R 2 hydrogen or halogen, R 3 halo, R 4 hydroxy, alkoxy, alkoxyalkoxy, cycloalkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, NO 2, CN, halogen or cyanoalkyl , Phenoxy, phenoxyalkyl, phenylalkoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, AOH, SH, halogen, CN and the like. a. mean next to formulation aids. formula
Description
R12, R13 = unabhängig voneinander Wasserstoff, (C1-C4J-AIkYl, oder zusammen mit dem sieR 12 , R 13 = independently of one another hydrogen, (C 1 -C 4 -alkyl), or together with them
verbindenden Stickstoffatom einen 3- bis 7gliedrigen Ring bilden, wobei eine """ Methylengruppe durch O, S oder NR7 ersetzt sein kann und der bis zu dreifach durch (C1-C4J-AIkYl substituiert sein kann,form a 3- to 7-membered ring, wherein a """methylene group may be replaced by O, S or NR 7 and which may be substituted up to three times by (C 1 -C 4 -alkyl),
Phenyl oder Benzyl, die beide im Phenylring bis zu dreifach durch Halogen, (C1-C4J-AIkYl, (C,-C4)-Alkoxy, (^-QJ-Alkoxycarbonyl, CF3 oder NO2 substituiert sein können,Phenyl or benzyl, both of which may be substituted in the phenyl ring up to three times by halogen, (C 1 -C 4 -alkyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 -alkoxycarbonyl, CF 3 or NO 2) ,
R14, R15 = unabhängig voneinander Wasserstoff, (C1-C4J-AIkYl oder Phenyl, das bis zu dreifachR 14 , R 15 = independently of one another hydrogen, (C 1 -C 4 ) -alkyl or phenyl, which may be up to three times
durch Halogen oder (C,-C4)-Alkyl substituiert sein kann,may be substituted by halogen or (C, -C 4 ) -alkyl,
R16 = (C1-C4J-AIkYl, das bis zu dreifach durch Halogen, (C1-C4J-AIkOXy, (Ci-C4)-Alkylthio, CN,R 16 = (C 1 -C 4 ) -alkyl which is up to three times halogen, (C 1 -C 4 -alkoxy, (C 1 -C 4 ) -alkylthio, CN,
Phenyl oder Phenyl, das bis zu zweifach durch Halogen, (C1-C4J-AIkYl, (C1-C4J-AIkOXy, CF3, NO2 substituiert ist, substituiert sein kann, oder Phenyl, das ein- bis dreifach durch Halogen, (C1-C4J-AIkYl, (C1-C4J-AIkOXy, (C^dJ-Alkoxycarbonyl, CF3 oder NO2 substituiert sein kann,Phenyl or phenyl which may be substituted up to two times by halogen, (C 1 -C 4 alkyl), (C 1 -C 4 ) -alkoxy, CF 3 , NO 2 , or phenyl, the one-bis may be substituted in trisubstituted by halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4) -alkoxy, (C 1 -C 3) -alkoxycarbonyl, CF 3 or NO 2 ,
η = die ZahM, 2 oder 3 undη = the number, 2 or 3 and
ρ = die Zahl O, 1 oder 2ρ = the number O, 1 or 2
bedeuten, enthalten neben Formulierungshilfsmitteln.mean, contain besides formulation aids.
2. Verwendung der Verbindungen der Formel I, dadurch gekennzeichnt, daß sie als Herbizide eingesetzt werden.2. Use of the compounds of the formula I, characterized gekennzeichnt that they are used as herbicides.
3. Verfahren zur Bekämpfung von unerwünschten Pflanzen in Nutzpflanzenkulturen, dadurch gekennzeichnet, daß man eine wirksame Menge einer Verbindung der Formel I von Anspruch 1 auf die Schadpflanzen oder die Anbaufläche aufbringt.3. A method for controlling undesirable plants in crops, characterized in that applying an effective amount of a compound of formula I of claim 1 to the harmful plants or the acreage.
Die Erfindung betrifft herbizide Mittel mit einem Gehalt an neuen 2-Aryl-4,5,6,7-tetrahydroisoindolinonen. Die erfindungsgemäßen Mittel werden angewandt in der Landwirtschaft für den Pflanzenschutz.The invention relates to herbicidal compositions containing new 2-aryl-4,5,6,7-tetrahydroisoindolinonen. The compositions according to the invention are used in agriculture for crop protection.
Es ist bekannt, daß 4,5,6,7-Tetrahydroisoindoiinone herbizide Eigenschaften aufweisen, s. EP-A 40 849, EP-A 41 256, DE-OSIt is known that 4,5,6,7-Tetrahydroisoindoiinone have herbicidal properties, s. EP-A 40 849, EP-A 41 256, DE-OS
Die herbizide Aktivität und die Selektivität dieser Verbindungen ist jedoch nicht immer voll befriedigend.However, the herbicidal activity and the selectivity of these compounds are not always fully satisfactory.
Ziel der Erfindung ist die Bereitstellung neuer Mittel mit starker herbizider Wirkung, die geeignet sind für die selektive Unkrautbekämpfung in Nutzpflanzenkulturen.The aim of the invention is the provision of new agents with strong herbicidal activity, which are suitable for the selective weed control in crops.
Darlegung des Wesens der ErfindungExplanation of the essence of the invention
Der Erfindung liegt die Aufgabe zugrunde, neue Verbindungen mit den gewünschten Eigenschaften aufzufinden, die als Wirkstoff inThe invention has for its object to find new compounds with the desired properties, as the active ingredient in
herbiziden Mitteln geeignet sind.herbicidal agents are suitable.
Es wurden nun neue 4,5,6,7-Tetrahydroisoindolinone gefunden, die überraschenderweise über eine wesentlich stärkere selektiveThere are now new 4,5,6,7-Tetrahydroisoindolinone found that surprisingly a much stronger selective
Herbizid-Wirkung verfugen.Herbicidal activity.
Erfindungsgemäß werden als Wirkstoff in den neuen herbiziden Mitteln Verbindungen der Formel IAccording to the invention as active ingredient in the new herbicidal compositions, compounds of the formula I.
angewandt, worinapplied, in which
R1 = (C,-C4)-Alkyl oder WasserstoffR 1 = (C 1 -C 4 ) -alkyl or hydrogen
R2 = Wasserstoff oder Halogen ,R 2 = hydrogen or halogen,
R3 = HalogenR 3 = halogen
R" = Hydroxy, (C,-C4)-Alkoxy, (C1-C4)AIkOXy-(C1-Ci)-BIkOXy, (C3-Ce)-Cycloalkoxy, (C3-C6)-Alkenyloxy,.(C3-Ce)-Alkinyloxy,R "= hydroxy, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -alkoxy (C 1 -C 6 ) -bikoxy, (C 3 -C e ) -cycloalkoxy, (C 3 -C 6 ) Alkenyloxy,. (C 3 -Ce) -alkynyloxy,
(C,-C4)-Alkylthio, (C,-C4)-Alkylsulfinyl, (C,-C4)-Alkylsulfonyl, NO2, CN, Halogen-(C,-C„)-alkyl mit einem ödere mehreren Halogenatomen, Mono-Cyano-(C,-C4)-alkyl, Phenoxy, Phenoxy-(C,-C4)-alkyl, Phenyl-(C,-C4)-alkoxy, Phenylthio, Phenylsulfinyl, Phenylsulfonyl, wobei in den 6 letztgenannten Resten der Phenylring bis zu dreifach durch Halogen, (C,-C4)-Alkyl, (C1-C)-AIkOXy oder (C,-C4)-Alkoxycarbonyl substituiert sein kann, eine Gruppe der Formeln(C, -C 4) alkylthio, (C, -C 4) alkylsulfinyl, (C, -C 4) alkylsulfonyl, NO 2, CN, halo (C, -C ") - alkyl with a plurality ödere Halogen atoms, mono-cyano- (C 1 -C 4 ) -alkyl, phenoxy, phenoxy- (C 1 -C 4 ) -alkyl, phenyl- (C 1 -C 4 ) -alkoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, where in in the last six mentioned groups, the phenyl ring may be substituted by up to three times by halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) -alkoxycarbonyl, a group of the formulas
_C-X-r5} -0-P(YR6O2, -0-(C)n-C-X-R5 oder'_C-X-r5 } -O-P (YR 6 O 2 , -O- (C) n -CXR 5 or '
Ä *7 Ä * 7
-C-N=C-NH2 ,-CN = C-NH 2 ,
X = O, S oder NR8 X = O, S or NR 8
Y, Z = unabhängig voneinander O oder SY, Z = independently of one another O or S.
R5 = Wasserstoff, (Ci-C,2)-Alkyl, das bis zu 6fach durch Halogen und/oder bis zu dreifach durch (C1-C4)-Alkoxy,R 5 = hydrogen, (C 1 -C 2 ) -alkyl which is up to 6 times halogen and / or up to 3 times (C 1 -C 4 ) -alkoxy,
(C1-C4J-AIkOXy-(C1-C4J-BIkOXy, (C-CJ-Alkoxycarbonyl, (C,-C4)-Alkylthio, (C,-C4)-Alkylsulfonyl, (C,-C4)-Alkylsulfinyl, (C,-C4)-Alkylamino, Di-(C1-C4)-alkylamino, Furyl, Tetrahydrofuryl, Benzofuryl, Phenyl, Phenoxy, Benzyloxy, wobei die drei letztgenannten Reste im Phenylteil bis zu zweifach durch Halogen, (C1-C4J-AIkYl oder (C1-C4J-AIkOXy(C 1 -C 4 J-AIkOXy- (C 1 -C 4 J-BIkOXy, (C-CJ-alkoxycarbonyl, (C, -C 4) alkylthio, (C, -C 4) alkylsulfonyl, (C -C 4 ) alkylsulfinyl, (C, -C 4 ) alkylamino, di- (C 1 -C 4 ) alkylamino, furyl, tetrahydrofuryl, benzofuryl, phenyl, phenoxy, benzyloxy, where the last three radicals in the phenyl part up to two times by halogen, (C 1 -C 4 J-AIkYl or (C 1 -C 4 J-AIkOXy
substituiert sein können, substituiert sein kann,may be substituted,
(C3-C6)-Cycloalkyl, (C3-C6)-Alkenyl, Cyclohexenyl, (C3-Cs)-Alkinyl, Phenyl, das bis zu dreifach durch Halogen, (C1-C4J-AIkYl, (C,-C4)-Alkoxy oder (CT-CJ-Alkoxycarbonyl substituiert sein kann, ein in der Landwirtschaft einsetzbares Kation oder einen Rest der Formel -N = CR9R'0, wobei für den letztgenannten Rest R4 = -CO-OR5 (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -alkenyl, cyclohexenyl, (C 3 -C s ) -alkynyl, phenyl which is up to three times halogen, (C 1 -C 4 -alkyl) , (C, -C 4 ) -alkoxy or (CT-CJ-alkoxycarbonyl may be substituted, an agriculturally useful cation or a radical of the formula -N = CR 9 R ' 0 , where for the last-mentioned radical R 4 = - CO-OR 5
bedeuten muß,must mean
R6 = unabhängig voneinander (C,-C4)-Alkyl oder Benzyl,R 6 = independently of one another (C 1 -C 4 ) -alkyl or benzyl,
R' = unabhängig voneinander Wasserstoff, (C,-C4)-Alkyl oder-CCI3,R '= independently of one another hydrogen, (C 1 -C 4 ) -alkyl or -CCI 3 ,
R8 = Wasserstoff, (C,-C4)-Alkyl, das zusammen mit R5 und dem diese Reste verbindenden Stickstoffatom einen fünf- bisR 8 = hydrogen, (C 1 -C 4 ) -alkyl which, together with R 5 and the nitrogen atom connecting these radicals, has a five-bis
siebengliedrigen Heterocyclus bilden kann, der als Ringglieder 1 oder 2 Reste der Gruppe -0-, -S- oder -NR6-can form a seven-membered heterocycle which has as ring members 1 or 2 radicals of the group -O-, -S- or -NR 6 -
enthält und der bis zu dreifach durch (C1-C4J-AIkYl substituiert sein kann, R9, R'0 = unabhängig voneinander (C1-C4J-AIkYl, (C3-Ce)-Cycloalkyl, (C1-C1)AIkOXyCaTbOnYl, oder gemeinsam einecontains and which may be up to three times substituted by (C 1 -C 4 -alkyl-J, R 9, R '0 = independently (C 1 -C 4 J--alkyl, (C 3 -C s) cycloalkyl, ( C 1 -C 1 ) AIkOXyCaTbOnYl, or together one
(C2-C7)-Alkylenkette, A = OH, SH, Halogen, CN,(C 2 -C 7 ) -alkylene chain, A = OH, SH, halogen, CN,
einen Rest der Formelna remainder of the formulas
-OR", -SfOJpR11, -NR12R13 oder -NH-NR14R15, R'1 = (C1-C12J-AIkYl, (C1-C4J-AIkOXy-(C1-C4J-BIkYl, Phenoxy}C1-C4JaIkYl, BBnZyIoXy(C1-C4JaIkYl, wobei die beiden-OR ", -SFOJpR 11 , -NR 12 R 13 or -NH-NR 14 R 15 , R ' 1 = (C 1 -C 12 ) -alkyl, (C 1 -C 4 ) -alkoxy- (C 1 -) C 4 J-BIkyl, phenoxy} C 1 -C 4 -alkyl, BBn-cyanoyl (C 1 -C 4 -alkyl), where the two
letztgenannten Reste im Phenylring bis zu dreifach durch Halogen, (C1-C4J-AIkVl oder (C1-C4I-AIkOXy substituiertthe latter radicals in the phenyl ring up to three times by halogen, (C 1 -C 4 J AIkVl or (C 1 -C 4 I-AIkOXy substituted
sein können,could be,
(C1-C4)-Alkoxycarbonyl-(C1—C4)-alkyl, Phenyl oder Benzyl, die beide bis zu dreifach im Phenylring durch Halogen, (C,-C4)-Alkyl, (C1-C4J-AIkOXy, (C^CJ-Alkoxycarbonyi, (C-CJ-Alkoxycarbonyl-fCj-CJ-alkoxy, CF3 oder NO2 (C 1 -C 4 ) alkoxycarbonyl (C 1 -C 4 ) alkyl, phenyl or benzyl, both of which are up to three times in the phenyl ring by halogen, (C, -C 4 ) alkyl, (C 1 -C 4 J-alkoxy, (C 1 -C 6 -alkoxycarbonyi, (C 1 -C 6 -alkoxycarbonyl-Fcj-CJ-alkoxy, CF 3 or NO 2
substituiert sein können, eine Gruppe der Formelnmay be substituted, a group of formulas
-C-R16, -C-0R16 oder -C-NH-Rlß, Ii U Il-CR 16 , -C-0R16 or -C-NH-Rlβ, Ii U Il
0 0 00 0 0
R12, R'3 = unabhängig voneinander Wasserstoff, (C1-C4J-AIkYl, oder zusammen mit dem sie verbindenden StickstoffatomR 12 , R ' 3 = independently of one another hydrogen, (C 1 -C 4 ) -alkyl or, together with the nitrogen atom connecting them
einen 3- bis 7gliedrigen Ring bilden, wobei eine Methylengruppe durch 0, S oder NR7 ersetzt sein kann und derbisform a 3- to 7-membered ring wherein one methylene group may be replaced by O, S or NR 7 and the bis
zu dreifach durch (C1-C4J-AIkYl substituiert sein kann,may be substituted in trisubstituted by (C 1 -C 4 ) -alkyl,
Phenyl oder Benzyl, die beide im Phenylring bis zu dreifach durch Halogen, (C1-C4J-AIkYl, (C1-C4J-AIkOXy,Phenyl or benzyl, both in the phenyl ring up to three times by halogen, (C 1 -C 4 -alkyl (C 1 -C 4 ) -alkoxy,
(C,-C4)-Alkoxycarbonyl, CF3 oder NO2 substituiert sein können, R'4, R'5 = unabhängig voneinander Wasserstoff, (C,-C4J-Alkyl oder Phenyl, das bis zu dreifach durch Halogen oderR '4, R' 5 may be substituted (C, -C 4) alkoxycarbonyl, CF 3 or NO 2, independently of one another hydrogen, (C, -C 4 J-alkyl or phenyl which is up to trisubstituted by halogen or
(C1-C4J-AIkYl substituiert sein kann, R'6 = (C,-C4)-Alkyl, das bis zu dreifach durch Halogen, (C,-C4)-Alkoxy, (C,-C4)-Alkylthio, CN, Phenyl oder Phenyl, das bis(C 1 -C 4 alkyl group may be substituted, R ' 6 = (C, -C 4 ) alkyl which may be up to three times by halogen, (C, -C 4 ) alkoxy, (C, -C 4 ) -Alkylthio, CN, phenyl or phenyl, the bis
zu zweifach durch Halogen, (C1-C4J-AIkYl, (C1-C4J-AIkOXy, CF3, NO2 substituiert ist, substituiert sein kann, oder Phenyl, das ein- bis dreifach durch Halogen, (C1-C4J-AIkYl, (C1-C4J-AIkOXy, (C1-C4J-AIkOXyCaTbOnYl, CF3 oder NO2 is monosubstituted by halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy, CF 3 , NO 2 , or phenyl which is mono- to trisubstituted by halogen, (C J-1 -C 4 -alkyl, (C 1 -C 4 J -alkoxy, (C 1 -C 4 J-AIkOXyCaTbOnYl, CF 3 or NO 2
substituiert sein kann, η = die Zahl 1, 2 oder 3 undmay be substituted, η = the number 1, 2 or 3 and
ρ = dieZahl O, 1 oder 2ρ = the number O, 1 or 2
bedeuten.mean.
Halogen bedeutet insbesondere F, Cl oder Br. Als für die Landwirtschaft einsetzbare Kationen kommen beispielsweise in Betracht Alkali-, Erdalkalikationen wie Na, K, Ca, Mg-Ionen, oder gegebenenfalls substituierte Ammoniumkationen. Als Heterocyclen kommen im FalleHalogen in particular denotes F, Cl or Br. Suitable cations which can be used for agriculture are, for example, alkali metal, alkaline earth cations such as Na, K, Ca, Mg ions or optionally substituted ammonium cations. As heterocycles come in the case
R8-N-R5 oder im Falle -NR12R13 bevorzugt in Frage: Morpholin, Piperazin, Piperidin, Pyrrolidin.R 8 -NR 5 or in the case of -NR 12 R 13 is preferably: morpholine, piperazine, piperidine, pyrrolidine.
Die Verbindungen der Formel I können auch als reine Stereoisomeren (z. B. im Falle R4 = -O[C(R7)2]„-CO-X-R5) oder als derenThe compounds of the formula I can also be used as pure stereoisomers (for example in the case R 4 = -O [C (R 7 ) 2 ] "- CO-XR 5 ) or as theirs
Gemische vorliegen. Alle diese Isomeren werden von vorliegender Erfindung umfaßt.Mixtures are present. All of these isomers are encompassed by the present invention.
Von den Verbindungen der Formel I sind bevorzugt solche, bei denen R2 = H, F oder Cl, R3 = Cl oder Br,Of the compounds of the formula I, preference is given to those in which R 2 = H, F or Cl, R 3 = Cl or Br,
ir \ir \
R4 = -CO-X-R5,-O- -C- -CO-X-R5, (^-CJAIkoxy-fC-CiJ-alkoxy und im Falle R2 = F auch (C1-C4)AIkOXy,R 4 = -CO-XR 5 , -O- -C- -CO-XR 5 , (C 1 -C 6 -alkoxy) -fC-CiJ-alkoxy and in the case of R 2 = F also (C 1 -C 4 ) -alkoxy,
R5 = (C1-C6)AIkYl, das durch (C1-C4)AIkOXy oder (C1-C4J-AIkOXyCaTbOnYl substituiert sein kann oder (C3-C4)Alkinyl, R7 = beide unabhängig voneinander (C1-C4)AIkYl oder ein Rest R7 = H und der andere Rest R7 = (C1-C4)AIkYl oder -CCI3,R 5 = (C 1 -C 6) -alkyl which can be substituted by (C 1 -C 4) -alkoxy or (C 1 -C 4 J-AIkOXyCaTbOnYl or (C 3 -C 4) alkynyl, R 7 = independently of both each other (C 1 -C 4 ) AlkYl or a radical R 7 = H and the other radical R 7 = (C 1 -C 4 ) AlkYl or -CCI 3 ,
R8 = (C,-C4)Alkyl, A = OH, Cl oder SR11,R 8 = (C 1 -C 4 ) alkyl, A = OH, Cl or SR 11 ,
R11 = (C1-C6)AIkYl, (C1-C4)Alkoxycarbonyl(C1—C4)alkyl, Phenyl oder Benzyl, die beide bis zu 3fach wie oben angegeben substituiertR 11 = (C 1 -C 6 ) AlKyl, (C 1 -C 4 ) alkoxycarbonyl (C 1 -C 4 ) alkyl, phenyl or benzyl, both of which are substituted up to 3-fold as indicated above
sein können, X = O,S und η = 1 bedeuten.X = O, S and η = 1.
Gegenstand der vorliegenden Erfindung sind auch Verfahren zur Herstellung der Verbindungen der Formel I, dadurch gekennzeichnet, daß man a) eine Verbindung der Formel IlThe present invention also provides processes for the preparation of the compounds of the formula I, characterized in that a) a compound of the formula II
(II)(II)
reduziert undreduced and
b) die unter a) erhaltenen Verbindungen der Formel I mit A = OH gegebenenfalls durch Umsetzung b^ mit einer Verbindung der Formel Ci-CO-R16, CI-CO-OR16 oder R16-NCO in Gegenwart einer Base oder b2) mit einer Verbindung der Formel R11-Hal (HaI = Cl, Br, J) in Gegenwart einer Base, oder b3) mit einem Isocyanat R16-N = C = O gegebenenfalls in Gegenwart einer Base, oder b4) mit einem anorganischen Säurechlorid wie SOCI2, POCI3, PCI3 in andere Verbindungen der Formel I überführt und die unter b4) erhaltenen Verbindungen der Formel I gegebenenfalls mit einem Alkalimetallfluorid, -bromid oder -jodid oder mit einem Alkalicyanid oder mit einer Verbindung der Formel HOR", HSR11, HNR12R13, oder H2N-NR14R15 umsetzt oder die unter b,J erhaltenen Verbindungen im Falle A = S-R11 gegebenenfalls oxidiert.b) the compounds obtained under a) of formula I with A = OH, if appropriate, by reacting b ^ with a compound of formula C-CO-R 16, CI-CO-OR 16, or R 16 -NCO, in the presence of a base or b 2 ) with a compound of the formula R 11 -Hal (Hal = Cl, Br, J) in the presence of a base, or b 3 ) with an isocyanate R 16 -N = C = O, if appropriate in the presence of a base, or b 4 ) an inorganic acid chloride such as SOCl 2 , POCl 3 , PCI 3 converted into other compounds of formula I and obtained under b 4 ) compounds of formula I optionally with an alkali metal fluoride, bromide or iodide or with an alkali metal or with a compound of formula HOR ", HSR 11 , HNR 12 R 13 , or H 2 N-NR 14 R 15 or the compounds obtained under b, J optionally oxidized in case of A = SR 11 .
Im Falle der Reduktion (Verfahrensvariante a) wird als Reduktionsmittel vorzugsweise ein Metallhydrid wie z. B. NaBH4 in einem organischen Lösungsmittel eingesetzt, wie z. B. Methanol, Ethanol oder auch Ether, Tetrahydrofuran und Dimethoxyethan bei Temperaturen zwischen O und 800C, vorzugsweise bei 20-400C, s. a. Rocz. Chem., 49, 1671 (1975).In the case of reduction (process variant a) is preferably a reducing agent as a metal hydride such. B. NaBH 4 used in an organic solvent, such as. As methanol, ethanol or ether, tetrahydrofuran and dimethoxyethane at temperatures between 0 and 80 0 C, preferably at 20-40 0 C, see Rocz. Chem., 49, 1671 (1975).
Die Verbindungen der allgemeinen Formel Il sind zum Teil bekannt, (s. Chem Ber. [1903], S. 996-1007), oder lassen sich einfach nach üblichen Methoden aus den entsprechenden Anilinen mit 3,4,5,6-Tetrahydrophthalsäureanhydrid herstellen.The compounds of the general formula II are known in some cases (see Chem Ber [1903], pages 996-1007), or can be prepared simply by conventional methods from the corresponding anilines with 3,4,5,6-tetrahydrophthalic anhydride ,
Bei der Verfahrensvariante b,) und b2) wird als Base eine anorganische Base wie beispielsweise K2CO3 oder eine organische Base, wie beispielsweise NEt3 oder Pyridin eingesetzt. Bei der Verfahrensvariante b3) kann als Base ein organisches Amin wie Triethylamin oder 1/4-Diazabicyclo-(2,2,2)octan eingesetzt werden. Die unter b4) genannte Umsetzung mit einem Alkalimetallfluorid-, -bromid-, -jodid oder -cyanid erfolgt vorzugsweise mittels Phasentransferkatalyse; zur Phasentransferkatalyse; zur Phasentransferkatalyse s.In the process variant b,) and b 2 ) is used as the base, an inorganic base such as K 2 CO 3 or an organic base, such as NEt 3 or pyridine. In the process variant b 3 ) can be used as the base, an organic amine such as triethylamine or 1 / 4-diazabicyclo (2,2,2) octane. The reaction with an alkali metal fluoride, bromide, iodide or cyanide mentioned under b 4 ) is preferably carried out by means of phase transfer catalysis; for phase transfer catalysis; for phase transfer catalysis s.
H. Böhme, U. Sitorus, Chemiker Ztg. 95 37 (1972). Als Alkalimetallverbindung wird bevorzugt die Na oder K-Verbindung eingesetzt.H. Böhme, U. Sitorus, chemist Ztg. 95 37 (1972). The alkali metal compound used is preferably the Na or K compound.
Die Oxidation der Verbindungen der Formel I mit A = SR" erfolgt in bekannter Weise z. B. mit Wasserstoffperoxid oder mitThe oxidation of the compounds of the formula I where A = SR "is carried out in a known manner, for example with hydrogen peroxide or with
m-Chlorperbenzoesäure; s. Houben-Weyl, Methoden der organischen Chemie Bd. IX S. 211, 227.m-chloroperbenzoic acid; s. Houben-Weyl, Methoden der organischen Chemie Bd. IX, p. 211, 227.
Die erfindungsgemäßen Verbindungen der Formel I weisen eine ausgezeichnete herbizide Wirksamkeit gegen ein breites Spektrum wirtschaftlich wichtiger mono- und dikotyler Schadpflanzen auf. Auch schwer bekämpfbare perennierende Unkräuter, die aus Rhizomen, Wurzelstöcken oder anderen Dauerorganen austreiben, werden durch die Wirkstoffe gut erfaßt. Dabei ist es gleichgültig,The compounds of the formula I according to the invention have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. Even difficult to control perennial weeds, which expel from rhizomes, rhizomes or other permanent organs, are well detected by the active ingredients. It does not matter
ob die Substanzen im Vorsaat-, Vorauflauf- oder Nachauflaufverfahren ausgebracht werden.whether the substances are applied in the pre-sowing, pre-emergence or post-emergence process.
Werden die erfindungsgemäßen Verbindungen von dem Keimen auf die Erdoberfläche appliziert, so wird entweder das Auflaufen der Unkrautkeimlinge vollständig verhindert, oder die Unkräuter wachsen bis zum Keimblattstadium heran, stellen jedoch dann ihrIf the compounds according to the invention are applied by the germination to the surface of the earth, either the emergence of the weed seedlings is completely prevented, or the weeds grow up to the cotyledon stage, but then provide it
Wachstum ein und sterben schließlich nach Ablauf von drei bis fünf Wochen vollkommen ab.Growth and finally die off after three to five weeks.
Beispielsweise können folgende Schadpflanzen bekämpft werden:For example, the following harmful plants can be combated:
Schadgräser wieGrass weeds like
Avena fatua, Alopecurus sp., Lolium sp., Setaria sp., Digitaria sp., Sorghum halepense, Echinochloa sp., Agropyron sp.: CynodonAvena fatua, Alopecurus sp., Lolium sp., Setaria sp., Digitaria sp., Sorghum halepense, Echinochloa sp., Agropyron sp. : Cynodon
sp., Phalaris sp.,sp., Phalaris sp.,
Dikotyle Pflanzen wieDicotyledonous plants like
Lamium sp., Veronica sp., Galium sp., Stellaria sp., Matricaria sp., Papaver sp., Centauria sp., Amaranthus sp., Galinsoga sp., Mercurialis sp., Sida sp., Abutilon sp., Ambrosia sp., Xanthium sp., Cirsium sp., Artemisia sp., Rumex sp., Convolvulis sp., IpomeaLamium sp., Veronica sp., Galium sp., Stellaria sp., Matricaria sp., Papaver sp., Centauria sp., Amaranthus sp., Galinsoga sp., Mercurialis sp., Sida sp., Abutilon sp., Ambrosia sp , Xanthium sp., Cirsium sp., Artemisia sp., Rumex sp., Convolvulis sp., Ipomea
sp., Sinapis sp.sp., Sinapis sp.
Bei Applikation der Wirkstoffe auf die grünen Pflanzenteile im Nachauflaufverfahren tritt ebenfalls sehr rasch nach der Behandlung ein drastischer Wachstumsstop ein, und die Unkrautpflanzen bleiben in dem zum Applikationszeitpunkt vorhandenen Wachstumsstadium stehen oder sterben nach einer gewissen Zeit mehr oder weniger schnell ganz ab; so daß auf diese Weise eine für die Kulturpflanzen schädliche Unkrautkonkurrenz sehr früh und nachhaltig durch den Einsatz der neuen erfindungsgemäßenWhen the active ingredients are applied to the green parts of the plants postemergence, a drastic growth stop also occurs very rapidly after the treatment, and the weed plants remain in the growth stage present at the time of application or die off more or less rapidly after a certain time; so that in this way harmful to the crop weed competition very early and sustainable by the use of the new invention
Mittel beseitigt werden kann.Means can be eliminated.
Obgleich die erfindungsgemäßen Verbindungen eine ausgezeichnete herbizide Aktivität gegenüber mono- und dikotylen Unkräutern aufweisen, werden Kulturpflanzen wirtschaftlich bedeutender Kulturen wie z. B. Weizen, Gerste, Roggen, Reis, Mais, Zuckerrübe, Baumwolle und Soja nur unwesentlich oder gar nicht geschädigt. Die vorliegenden Verbindungen eignen sich aus diesen GründenAlthough the compounds of the invention have excellent herbicidal activity against mono- and dicotyledonous weeds, crops of economically important crops such. As wheat, barley, rye, rice, corn, sugar beet, cotton and soy only insignificant or not damaged. The present compounds are suitable for these reasons
sehr gut zur selektiven Bekämpfung von unerwünschtem Pflanzenwuchs in landwirtschaftlichen Nutzpflanzungen.very good for the selective control of undesired plant growth in agricultural crops.
Darüber hinaus weisen die erfindungsgemäßen Verbindungen wachstumsregulatorische Eigenschaften bei Kulturpflanzen auf. Sie greifen regulierend in den pflanzeneigenen Stoffwechsel ein und können damit zur Ernteerleichterung wie z. B. durch Auslösen von Desikkation, Abszission und Wuchsstauchung eingesetzt werden. Desweiteren eignen sie sich auch zur generellen Steuerung und* Hemmung von unerwünschtem vegetativen Wachstum, ohne dabei die Pflanzen abzutöten. Eine Hemmung des vegetativen Wachstums spielt bei vielen mono- und dikotylen Kulturen eine große Rolle, da das Lagern hierdurch verringert oder völligIn addition, the compounds according to the invention have growth-regulatory properties in crop plants. They regulate into the plant's metabolism and can thus be used to facilitate harvesting such as. B. by triggering desiccation, abscission and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous cultures, as storage is thereby reduced or completely eliminated
verhindert werden kann.can be prevented.
Die erfindungsgemäßen Mittel können als Spritzpulver, emulgierbare Konzentrate, versprühbare Lösungen, Stäubemittel,The compositions of the invention can be used as wettable powders, emulsifiable concentrates, sprayable solutions, dusts,
Beizmittel, Dispersionen, Granulate oder Mikrogranulate in den üblichen Zubereitungen angewendet werden.Beizmittel, dispersions, granules or microgranules are used in the usual preparations.
Spritzpulver sind in Wasser gleichmäßig dispergierbare Präparate, die neben dem Wirkstoff außer gegebenenfalls einem Verdünnungs- oder Inertstoff noch Netzmittel, z. B. polyoxethylierte Alkylphenole, polyoxethylierte Fettalkohole, Alkyl- oder Alkylphenylsulfonate und Dispergiermittel, z. B. ligninsulfonsaures Natrium, 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium, dibutylnaphthalinsulfonsaures Natrium oder auch oleoylmethyltaurinsaures Natrium enthalten. Die Herstellung erfolgt in üblicherInjectable powders are preparations which are uniformly dispersible in water and, in addition to the active substance, may also contain wetting agents, for example a diluent or inert substance. As polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenylsulfonates and dispersants, eg. As sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalenesulfonate sodium or oleoylmethyltaurine acid. The production takes place in usual
Weise, z. B. durch Mahlen und Vermischen der Komponenten.Way, z. B. by grinding and mixing of the components.
Emulgierbare Konzentrate können z. B. durch Auflösen des Wirkstoffes in einem inerten organischen Lösungsmittel, z. B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten oder Kohlenwasserstoffen unter Zusatz von einem oder mehreren Emulgatoren hergestellt werden. Bei flüssigen Wirkstoffen kann der Lösungsmittelanteil auch ganz oder teilweiseEmulsifiable concentrates may, for. B. by dissolving the active ingredient in an inert organic solvent, for. As butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers. In the case of liquid active substances, the solvent fraction may also be wholly or partly
entfallen. Als Emulgatoren können beispielsweise verwendet werden: Alkylarylsulfonsaure Calciumsalze wieomitted. Examples of suitable emulsifiers are: alkylarylsulfonic acid calcium salts such as
Ca-dodecylbenzolsulfonat oder nichtionische Emulgatoren wie Fettsäurepolyglykolester, Alkyl-arylpolyglykolether,Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers,
Fettalkoholpolyglykolether, Propylenoxid-Ethylenoxid-Kondensationsprodukte, Fettalkohol-Propylenoxid-Ethylenoxid-Kondensationsprodukte, Alkyl polyglykolether, Sorbitanf ensäureester, Polyoxethylensorbitanfensäureester oder Polyoxethylensorbitester.Fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, fatty alcohol-propylene oxide-ethylene oxide condensation products, alkyl polyglycol ether, sorbitan fensäureester, Polyoxethylensorbitanfensäureester or Polyoxethylensorbitester.
Stäubemittel kann man durch Vermählen des Wirkstoffes mit feinverteilten, festen Stoffen, z. B. Talkum, natürlichen Tonen wieDusts can be obtained by grinding the active ingredient with finely divided, solid substances, eg. As talc, natural clays like
Kaolin, Bentonit, Pyrophillit oder Diatomeenerde erhalten.Kaolin, bentonite, pyrophillite or diatomaceous earth obtained.
Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen von Wirkstoffkonzentrationen mittels Bindemitteln, z. B. Polyvinylalkohol, polyacrylsaurem Natrium oder auch Mineralölen auf die Oberfläche von Trägerstoffen wie Sand, Kaolinite oder von granuliertem Inertmaterial. Auch können geeignete Wirkstoffe in der für die Herstellung von Düngemittelgranulaten üblichen Weise, gewünschtenfalls in Mischung mitGranules can be prepared either by spraying the active ingredient on adsorptive, granulated inert material or by applying active substance concentrations by means of binders, for. As polyvinyl alcohol, polyacrylic acid sodium or mineral oils on the surface of carriers such as sand, kaolinites or granulated inert material. Also suitable active ingredients in the usual manner for the production of fertilizer granules, if desired in admixture with
Düngemitteln, granuliert werden.Fertilizers, to be granulated.
In Spritzpulvern beträgt die Wirkstoffkonzentration ζ. B. etwa'10 bis 90 Gew.-%, der Rest zu 100 Gew.-% besteht aus üblichen Formulierungsbestandteilen. Bei emulgierbaren Konzentraten kann die Wirkstoffkonzentration etwa 5 bis 80 Gew.-% betragen.In wettable powders, the active ingredient concentration is ζ. B. about '10 to 90 wt .-%, the remainder to 100 wt .-% consists of conventional formulation ingredients. For emulsifiable concentrates, the active ingredient concentration may be about 5 to 80% by weight.
Staubförmige Formulierungen enthalten meisten 5 bis 20 Gew.-% an Wirkstoff, versprühbare Lösungen etwa 2 bis 20 Gew.-%. Bei Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt und welcheDusty formulations contain most 5 to 20 wt .-% of active ingredient, sprayable solutions about 2 to 20 wt .-%. For granules, the active ingredient content depends in part on whether the active compound is liquid or solid and which
Granulierhilfsmittel, Füllstoffe usw. verwendet werden.Granulation aids, fillers, etc. are used.
Daneben enthalten die genannten Wirkstofformulierungen gegebenenfalls die jeweils üblichen Haft-, Netz-, Dispergier-, Emulgier-,In addition, the active substance formulations mentioned optionally contain the customary adhesive, wetting, dispersing, emulsifying,
Penetrations-, Lösungsmittel, Füll- oder Trägerstoffe.Penetration, solvents, fillers or carriers.
Zur Anwendung werden die in handelsüblicher Form vorliegenden Konzentrate gegebenenfalls in üblicher Weise verdünnt, z. B. bei Spritzpulvern, emulgierbaren Konzentraten, Dispersionen und teilweise auch bei Mikrogranulaten mittels Wasser. Staübförmige und granulierte Zubereitungen sowie versprühbare Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inertenFor use, the present in commercial form concentrates are optionally diluted in a conventional manner, for. As in wettable powders, emulsifiable concentrates, dispersions and sometimes also in microgranules by means of water. Staübförmige and granulated preparations and sprayable solutions are usually no longer before use with other inert
Stoffen verdünnt.Diluted substances.
Mit den äußeren Bedingungen wie Temperatur, Feuchtigkeit u. a. variiert die erforderliche Aufwandmenge. Sie kann innerhalb weiter Grenzen schwanken, z. B. zwischen 0,005 und 10,0 kg/ha oder mehr Aktivsubstanz, vorzugsweise liegt sie jedoch zwischen 0,01 und 2 kg/ha.With the external conditions such as temperature, humidity and. a. the required application rate varies. It can vary within wide limits, eg. B. between 0.005 and 10.0 kg / ha or more active substance, but it is preferably between 0.01 and 2 kg / ha.
Auch Mischungen oder Mischformulierungen mit anderen Wirkstoffen, wie z. B. Insektiziden, Akariziden, Herbiziden, Düngemitteln, Wachstumsregulatoren oder Fungiziden sind gegebenenfalls möglich.Also mixtures or mixed formulations with other active ingredients, such as. As insecticides, acaricides, herbicides, fertilizers, growth regulators or fungicides may be possible.
Ausführungsbeispielembodiment
Die Erfindung wird durch nachstehende Beispiele erläutert:The invention is illustrated by the following examples:
A. FormulierungsbeispieleA. Formulation Examples
Ein Stäubemittel wird erhalten, indem man 10 Gewichtsteile Wirkstoff und 90 Gewichtsteile Talkum oder Inertstoff mischt und inA dusting agent is obtained by mixing 10 parts by weight of active compound and 90 parts by weight of talc or inert substance and mixing in
einer Schlagmühle zerkleinert.crushed a hammer mill.
Ein in Wasser leicht dispergierbares, benetzbares Pulver wird erhalten, indem man 25 Gewichtsteile Wirkstoff, 64 Gewichtsteile kaolinhaltigen Quarz als Inertstoff, 10 Gewichtsteile ligninsulfonsaures Kalium und 1 Gewichtsteil oleoylmethyltaurinsaures NatriumA wettable powder readily dispersible in water is obtained by adding 25 parts by weight of active ingredient, 64 parts by weight of kaolin-containing quartz as an inert, 10 parts by weight of potassium lignosulfonate and 1 part by weight of oleoylmethyltaurine sodium
als Netz- und Dispergiermittel mischt und in einer Stiftmühle mahlt.as a wetting and dispersing agent and grinding in a pin mill.
Ein in Wasser leicht dispergierbares Dispersionskonzentrat wird erhalten, indem man 20 Gewichtsteile Wirkstoff, mit 6 Gewichtsteilen Alkylphenolpolyglykolether (®Triton x 207), 3 Gewichtsteilen Isotridecanolpolyglykolether (8 AeO) und 71 Gewichtsteilen paraffinischem Mineralöl (Siedebereich z. B. etwa 255 bis über 377 "C) mischt und in einer Reibkugelmühle aufA water-dispersible dispersion concentrate is obtained by adding 20 parts by weight of active ingredient, 6 parts by weight of alkylphenol polyglycol ether (®Triton x 207), 3 parts by weight of isotridecanol polyglycol ether (8AeO) and 71 parts by weight of paraffinic mineral oil (boiling range, e.g., about 255 to over 377 "). C) and mixed in a ball mill
eine Feinheit von unter 5 Mikron vermahlt.a fineness of less than 5 microns milled.
Ein emulgierbares Konzentrat wird erhalten aus 15 Gewichtsteilen Wirkstoff, 75 Gewichtsteilen Cyclohexanon als Lösungsmittel undAn emulsifiable concentrate is obtained from 15 parts by weight of active compound, 75 parts by weight of cyclohexanone as solvent and
10 Gewichtsteilen oxethyliertes Nonylphenol (10 AeO) als Emulgator.10 parts by weight of ethoxylated nonylphenol (10 AeO) as emulsifier.
B. Chemische BeispieleB. Chemical Examples
Beispiel 1 2-(4-Chlor-2-fluor-5-methoxy-phenyl)-3-hydroxy-4,5,6,7-tetrahydroisoindolinonExample 1 2- (4-Chloro-2-fluoro-5-methoxy-phenyl) -3-hydroxy-4,5,6,7-tetrahydroisoindolinone
46,5 g (0,15 mol) N-(4-Chlor-2-fluor-5-methoxy-phenyl)-3,4,5,6-tetrahydrophthalimid werden in 200 ml Methanol gelöst. Man gibt 7,6 g (0,20 mol) NaBH4 so zu, daß die Temperatur auf 30—35 °C ansteigt. Nach beendeter Zugabe wird noch 30 min bei RT gerührt und anschließend auf 800 ml Eiswasser gegossen. Der ausgefallene Niederschlag wird abgesaugt und getrocknet. Der getrocknete Niederschlag wird mit 100 ml Ether 10'min aufgekocht, im Eisbad gekühlt und erneut abgesaugt. Man erhält 39,3 g (84% d. Th.) 2-(4-Chlor-2-fluor-5-methoxy-phenyl)-3-hydroxy-4,5,6,7-tetrahydroisoindolinon in Form eines hellgrauen Pulvers mit Schmp. 194-1970C.46.5 g (0.15 mol) of N- (4-chloro-2-fluoro-5-methoxyphenyl) -3,4,5,6-tetrahydrophthalimide are dissolved in 200 ml of methanol. 7.6 g (0.20 mol) of NaBH 4 are added so that the temperature rises to 30-35 ° C. After completion of the addition is stirred for 30 min at RT and then poured onto 800 ml of ice water. The precipitate is filtered off with suction and dried. The dried precipitate is boiled with 100 ml of ether for 10 min, cooled in an ice bath and filtered off with suction again. This gives 39.3 g (84% of theory) of 2- (4-chloro-2-fluoro-5-methoxyphenyl) -3-hydroxy-4,5,6,7-tetrahydroisoindolinone in the form of a light gray powder with m. 194-197 0 C.
Beispiel 2 3-Chlor-2-(4-chlor-2-fluor-5-methoxy-phenyi)-4,5/6,7-tetrahydroisoindolinenExample 2 3-Chloro-2- (4-chloro-2-fluoro-5-methoxy-phenyl) -4,5 / 6,7-tetrahydroisoindolines
31,2 g (0,1 mol) 2-(4-Chlor-2-fluor-5-methoxy-phenyl)-3-hydroxy-4,5,6,7-tetrahydroisoindolinon (Beispiel 1) werden in 150 ml Methylenchlorid gelöst. Bei RT'1 tropft man 13,1 g (0,11 mol) Thionylchlorid zu. Man rührt 30 min bei RT und 1 h bei 400C. Die klare gelbe Lösung wird mit 100 ml H2O gewaschen, über Na2SO4 getrocknet und zur Trockene eingeengt. Man erhält 32,4 g (98% d. Th.) 3-Chlor-2-(4-Chlor-2-fluor-5-methoxy-phenyl)-4,5,6,7-tetrahydroisoindolinon in Form eines blaßgrünen Pulvers mit Schmp. 102-1050C. ·31.2 g (0.1 mol) of 2- (4-chloro-2-fluoro-5-methoxyphenyl) -3-hydroxy-4,5,6,7-tetrahydroisoindolinone (Example 1) are dissolved in 150 ml of methylene chloride solved. 13.1 g (0.11 mol) of thionyl chloride are added dropwise to RT ' 1 . The mixture is stirred at RT for 30 min and at 40 ° C. for 1 h. The clear yellow solution is washed with 100 ml of H 2 O, dried over Na 2 SO 4 and concentrated to dryness. This gives 32.4 g (98% of theory) of 3-chloro-2- (4-chloro-2-fluoro-5-methoxyphenyl) -4,5,6,7-tetrahydroisoindolinone in the form of a pale green powder with m.p. 102-105 0 C. ·
'' RT= Raumtemperatur Beispiel 3 2-(4-Chlor-2-fluor-5-methoxy-phenyl)-3-phenylmercapto-4,5,6,7-tetrahydroisoindolinonExample 3 2- (4-Chloro-2-fluoro-5-methoxyphenyl) -3-phenylmercapto-4,5,6,7-tetrahydroisoindolinone
33,0 g (0,1 mol) 3-Chlor-2-(4-chlor-2-fluor-5-methoxyphenyl)-4,5,6,7-tetrahydroisoindolinon (Bsp. 2) und 10,0 g (0,1 mol) NEt3 werden in 200 ml Toluol gelöst. Man tropft 11,0 g (0,1 mol) Thiophenol zu und rührt 4 h bei 60-700C. Das ausgefallene Ammoniumchlorid wird abgesaugt, die Mutterlauge 2ml mit 100 ml H2O gewaschen, über Na2SO4 getrocknet und eingedampft. Man erhält 38,0 g (97% d. Th.) 2-(4-Chlor-2-fluor-5-methoxy-phenyl)-3-phenylmercapto-4,5,6,7-tetrahydroisoindolinon in Form eines hellbraunen Öles.33.0 g (0.1 mol) of 3-chloro-2- (4-chloro-2-fluoro-5-methoxyphenyl) -4,5,6,7-tetrahydroisoindolinone (Ex. 2) and 10.0 g ( 0.1 mol) NEt 3 are dissolved in 200 ml of toluene. Is added dropwise 11.0 g (0.1 mol) of thiophenol and stirred for 4 h at 60-70 0 C, the precipitated ammonium chloride is filtered off with suction, the mother liquor 2ml washed with 100 ml H 2 O, dried over Na 2 SO 4 and evaporated , This gives 38.0 g (97% of theory) of 2- (4-chloro-2-fluoro-5-methoxyphenyl) -3-phenylmercapto-4,5,6,7-tetrahydroisoindolinone in the form of a light brown oil ,
Beispiel 4 2-(4-Chlor-2-fluor-5-methoxy-phenyl)-3-[4-(l-ethoxycarbonylethoxy)-phenoxy]-4,5,6,7-tetrahydroisoindolinonExample 4 2- (4-Chloro-2-fluoro-5-methoxy-phenyl) -3- [4- (1-ethoxycarbonylethoxy) -phenoxy] -4,5,6,7-tetrahydroisoindolinone
15,8 g (0,05 mol) 3-Chlor-2-(4-chlor-2-fluor-5-methoxyphenyl)-4,5,6,7-tetrahydroisoindolinon (Bsp. 2) in 50 ml Acetonitril tropft man bei 200C zu einer Lösung von 10,5 g (0,05 mol) 2-(4-Hydroxy-phenoxy)-propionsäureethylester in 100 ml Acetonitril. Bei RT gibt man portionsweise 1,5 g 80%iges Natriumhydrid zu. Man rührt 4 h bei 500C, gießt auf 300 ml Eiswasser und extrahiert mit 150 ml Methylenchlorid. Die Methylenchloridphase wird mit 150 ml H2O gewaschen, über Na2SO4 getrocknet und eindampft. Man erhält 23,2 g (95% d. Th.) 2-(4-Chlor-2-fluor-5-methoxy-phenyl)-3-[4-(l-ethoxycarbonyl-ethoxy)-phenoxy]-4,5,6,7rtetrahydroisoindolinon in Form eines hellbraunen Harzes.15.8 g (0.05 mol) of 3-chloro-2- (4-chloro-2-fluoro-5-methoxyphenyl) -4,5,6,7-tetrahydroisoindolinone (Ex. 2) in 50 ml of acetonitrile is added dropwise at 20 0 C to a solution of 10.5 g (0.05 mol) of ethyl 2- (4-hydroxy-phenoxy) propionate in 100 ml of acetonitrile. At RT, 1.5 g of 80% sodium hydride are added in portions. The mixture is stirred for 4 h at 50 0 C, poured onto 300 ml of ice water and extracted with 150 ml of methylene chloride. The methylene chloride phase is washed with 150 ml H 2 O, dried over Na 2 SO 4 and evaporated. This gives 23.2 g (95% of theory) of 2- (4-chloro-2-fluoro-5-methoxy-phenyl) -3- [4- (1-ethoxycarbonyl-ethoxy) -phenoxy] -4, 5,6,7-tetrahydroisoindolinone in the form of a light brown resin.
Beispiel 5 3-Acetyloxy-2-(4-chlor-2-fluor-5-methoxy-phenyl)-4,5,6,7-tetrahydroisoindolinonExample 5 3-Acetyloxy-2- (4-chloro-2-fluoro-5-methoxyphenyl) -4,5,6,7-tetrahydroisoindolinone
31,2 g (0,1 mol) 2-(4-Chlor-2-fluor-5-methoxy-phenyl)-3-hydroxy-4,5,6,7-tetrahydroisoindolinon (Bsp. 1) werden in 200 ml Dimethoxyethan gelöst. Bei 100C gibt man portionsweise 3,0 g Natriumhydrid (80%ig) zu und rührt 30 min bei 100C. Bei 100C tropft man 7,9 g (0,1 mol) Acetylchlorid zu und rührt anschließend 2 h bei 400C. Man gießt auf 400 ml Wasser und extrahiert mit 200 ml31.2 g (0.1 mol) of 2- (4-chloro-2-fluoro-5-methoxyphenyl) -3-hydroxy-4,5,6,7-tetrahydroisoindolinone (Ex. 1) are dissolved in 200 ml Dissolved dimethoxyethane. At 10 0 C are added in portions 3.0 g of sodium hydride (80%) and stirred for 30 min at 10 0 C at 10. 0 C is added dropwise 7.9 g (0.1 mol) of acetyl chloride and then stirred for 2 h at 40 0 C. It is poured onto 400 ml of water and extracted with 200 ml
Ether.Ether.
Nach Trocknen der organ. Phase über Na2SO4 und abdestillieren des Lösungsmittels erhält man 32,1 g (95% d. Th.) 3-Acetyloxy-2-(4-chlor-2-fluor-5-methoxy-phenyl)-4,5,6,7-tetrahydroisoindolinon in Form eines hellbraunen Öls.After drying the organ. Phase over Na 2 SO 4 and distilling off the solvent gives 32.1 g (95% of theory) of 3-acetyloxy-2- (4-chloro-2-fluoro-5-methoxyphenyl) -4.5, 6,7-tetrahydroisoindolinone in the form of a light brown oil.
2-(4-Chlor-2-fluor-5-methoxy-phenyl)-3-methoxycarbonyloxy-4,5,6,7-tetrahydroisoindolinon 31,2 g (0,1 mol) 2-(4-Chlor-2-fluor-5-methoxy-phenyl)-3-hydroxy-4,5,6,7-tetrahydroisoindolinon (Bsp. 1) und 8,7 g2- (4-Chloro-2-fluoro-5-methoxy-phenyl) -3-methoxycarbonyloxy-4,5,6,7-tetrahydroisoindolinone 31.2 g (0.1 mol) of 2- (4-chloro-2-) fluoro-5-methoxy-phenyl) -3-hydroxy-4,5,6,7-tetrahydroisoindolinone (Ex 1) and 8.7 g
Chlorameisensäuremethylester werden in 150 ml Dimethoxyethan gelöst. Bei 10°C gibt man portionsweise 3,0 g Natriumhydrid (80%ig) zu und rührt anschließend noch 2 h bei 300C. Man gießt auf 400 ml Eiswasser und extrahiert mit Ether. Man erhält 32,4 g (92% d. Th.) 2-(4-Chlor-2-fluor-5-methoxy-phenyl)-3-methoxycarbonyloxy-4,5,6,7-tetrahydroisoindolinon in Form eines hellbraunen Öls.Methyl chloroformate are dissolved in 150 ml of dimethoxyethane. At 10 ° C are added in portions 3.0 g sodium hydride (80% strength) and then stirred for a further 2 h at 30 0 C. It is poured onto 400 ml of ice water and extracted with ether. This gives 32.4 g (92% of theory) of 2- (4-chloro-2-fluoro-5-methoxyphenyl) -3-methoxycarbonyloxy-4,5,6,7-tetrahydroisoindolinone in the form of a light brown oil ,
Beispiel 7 2-{4-Chlor-2:fluor-5-methoxy-phenyl)-3-methylcarbamoyloxy-4,5,6,7-tetrahydroisoindolinonExample 7 2- {4-Chloro-2 : fluoro-5-methoxyphenyl) -3-methylcarbamoyloxy-4,5,6,7-tetrahydroisoindolinone
Man löst 31,2 g (0,1 mol) 2-(4-Chlor-2-fluor-5-methoxyphenyl)-3-hydroxy-4,5,6,7-tetrahydroisoindolinon (Bsp. 1) und 6,3 g (0,11 mol) ' Methylisocyanat in 200 ml Acetonitril und gibt 100 mg DABCO (1,4-Diazabicyclo[2.2.2]octan) zu. Nach 12 h Rühren bei RT wird das Lösungsmittel abdestilliert. Der verbleibende Rückstand wird in Ether aufgeschlämmt und abgesaugt. Man erhält 24,2 g (66% d. Th.) 2-(4-Chlor-2-fluor-5-methoxy-phenyl)-3-methoxycarbamoyloxy-4,5,6,7-tetrahydroisoindolinon in Form farbloser Kristalle mit Schmp. 148-1510C (Methanol).Dissolve 31.2 g (0.1 mol) of 2- (4-chloro-2-fluoro-5-methoxyphenyl) -3-hydroxy-4,5,6,7-tetrahydroisoindolinone (Ex 1) and 6.3 g (0.11 mol) of methyl isocyanate in 200 ml of acetonitrile, and 100 g of DABCO (1,4-diazabicyclo [2.2.2] octane) are added. After stirring for 12 h at RT, the solvent is distilled off. The remaining residue is slurried in ether and filtered with suction. This gives 24.2 g (66% of theory) of 2- (4-chloro-2-fluoro-5-methoxyphenyl) -3-methoxycarbamoyloxy-4,5,6,7-tetrahydroisoindolinone in the form of colorless crystals mp. 148-151 0 C (methanol).
Beispiel 8 2-{4-Chlor-2-fluor-5-methoxy-phenyl)-3-diethylamino-4,5,6,7-tetrahydroisoindolinonExample 8 2- {4-Chloro-2-fluoro-5-methoxy-phenyl) -3-diethylamino-4,5,6,7-tetrahydroisoindolinone
Zu 33,0 g (0,1 mol) 3-Chlor-2-(4-chlor-2-fluor-5-methoxyphenyl)-4,5,6,7-tetrahydroisoindolinon (Bsp. 2) in 200 ml Methylenchlorid tropft man bei 200C 14,6 g (0,2 mol) Diethylamin. Man rührt 4 h bei 20-250C, gibt 200 ml H2O dazu und trennt die organische Phase ab. Nach Trocknen über Na2SO4 wird das Lösungsmittel abdestilliert. Man erhält 32,5 g (92% d. Th.) 2-(4-Chlor-2-fluor-5-methoxyphenyl)-3-diethylamino-4,5,6,7-tetrahydroisoindolinon in Form eines gelben Öles.To 33.0 g (0.1 mol) of 3-chloro-2- (4-chloro-2-fluoro-5-methoxyphenyl) -4,5,6,7-tetrahydroisoindolinone (Ex. 2) is added dropwise in 200 ml of methylene chloride one at 20 0 C 14.6 g (0.2 mol) of diethylamine. The mixture is stirred for 4 h at 20-25 0 C, 200 ml of H 2 O are added and the organic phase is separated off. After drying over Na 2 SO 4 , the solvent is distilled off. This gives 32.5 g (92% of theory) of 2- (4-chloro-2-fluoro-5-methoxyphenyl) -3-diethylamino-4,5,6,7-tetrahydroisoindolinone in the form of a yellow oil.
2-(4-Chlor-2-fluor-5-methoxy-phenyl)-3-fluor-4,5,6,7-tetrahydroisoindolinon2- (4-chloro-2-fluoro-5-methoxy-phenyl) -3-fluoro-4,5,6,7-tetrahydroisoindolinon
33,0 g (0,1 mol) 3-Chlor-2-(4-chlor-2-fluor-5-methoxyphenyl)-4,5,6,7-tetrahydroisoindolinon (Bsp. 2) wird in 250 ml trockenem Acetonitril gelöst. Man gibt 14,5 g (0,25 mol) KF und 100 mg Kronenether (18-crown-6) zu und rührt 5 h bei 400C. Der.Ansatz wird auf 600 ml Wasser gegossen und mit Methylenchlorid extrahiert. Nach Abdestillieren des Acetonitrils erhält man 28,4 g (91 % d< Th.) 2-(4-Chlor-2-fluor-5-methoxy-phenyl)-3-fluor-4,5,6,7-tetrahydroisoindolinon in Form blaßgelber Kristalle mit Schmp. 88-900C.33.0 g (0.1 mol) of 3-chloro-2- (4-chloro-2-fluoro-5-methoxyphenyl) -4,5,6,7-tetrahydroisoindolinone (Ex. 2) is dissolved in 250 ml of dry acetonitrile solved. Are added to 14.5 g (0.25 mol) of KF and 100 mg of crown ether (18-crown-6) and stirred for 5 h at 40 0 C. Der.Ansatz is poured onto 600 ml water and extracted with methylene chloride. After distilling off the acetonitrile, 28.4 g (91% d <Th.) Of 2- (4-chloro-2-fluoro-5-methoxyphenyl) -3-fluoro-4,5,6,7-tetrahydroisoindolinone in Form pale yellow crystals with mp 88-90 0 C.
In analoger Weise erhält man die Verbindungen der folgenden Tabelle 1.The compounds of the following Table 1 are obtained in an analogous manner.
R1 R 1
N) OI N)N) OI N)
Fortsetzung Tabelle 1 Continued Table 1
Fortsetzung Tabelle 1 Continuation Table 1
Fortsetzung Tabelle 1 Continuation Table 1
Fortsetzung Tabelle 1 Continuation Table 1
-OH-OH
-Cl-Cl
Brbr
CHCH
-S-CH-CO2C2H5 -OH -Cl -SC2H5 -S-CH-CO 2 C 2 H 5 -OH-Cl -SC 2 H 5
CH3 CH 3
-S-CH-CO2C2H5 -S-C6H5 -OH -Cl-S-CH-CO 2 C 2 H 5 -SC 6 H 5 -OH-Cl
-SC2H5-s-CH2-<:o2c2H5 -SC 2 H 5 -s-CH 2 - <: o 2 c 2 H 5
CH3 CH 3
-S-CH-CO2C2H5 -S-CH-CO 2 C 2 H 5
gelbes Ölyellow oil
hellbraunes Harzlight brown resin
F F FF F F
F F F FF F F F
F F F FF F F F
Brbr
Cl Cl ClCl Cl Cl
Cl Br Br BrCl Br Br Br
Br Br Cl BrBr Br Cl Br
CH. ι J CH. ι J
-C-0-CH-C0oCoHril I I j -C-0-CH-C0 o C o H r il II j
-S-C6H5 -SC 6 H 5
-OH -Cl-OH-Cl
-OH -Cl -SC2H5 -OH-Cl -SC 2 H 5
-OCH2-C^CH-OCH 2 -C ^ CH
-OH -OH-OH OH
I roI ro
C. Biologische BeispieleC. Biological examples
Die Schädigung der Unkrautpflanzen bzw. die Kulturpflanzenverträglichkeit wurde gemäß einem Schlüssel bonitiert, in dem die Wirksamkeit durch Wertzahlen von 0-5 ausgedrückt ist. Dabei bedeutet: 0 = ohne Wirkung bzw. Schaden 1= 0- 20% Wirkung bzw. SchadenDamage to weed plants or crop plant compatibility was scored according to a key in which the effectiveness is expressed by values of 0-5. 0 = no effect or damage 1 = 0-20% effect or damage
2 = 20- 40% Wirkung.bzw. Schaden -2 = 20- 40% Effekt.bzw. Damage
3 = 40- 60% Wirkung bzw. Schaden3 = 40-60% effect or damage
4 = 60- 80% Wirkung bzw. Schaden4 = 60- 80% effect or damage
5 = 80-100% Wirkung bzw. Schaden 1. Unkrautwirkung im Vorauf lauf5 = 80-100% Effect or damage 1. Weed effect in the preliminary run
Samen bzw. Rhizomstücke von mono- und dikotylen Unkrautpflanzen wurden in Piastiköpfen (0 = 9 cm) in sandiger LehmerdeSeeds or rhizome pieces of monocotyledonous and dicotyledonous weed plants were grown in sandy loam soil in piastic heads (0 = 9 cm)
ausgelegt und mit Erde abgedeckt. Die in Form von benetzbaren Pulvern oder Emulsionskonzentraten formuliertendesigned and covered with earth. Formulated in the form of wettable powders or emulsion concentrates
erfindungsgemäßen Verbindungen wurden dann als wäßrige Suspensionen bzw. Emulsionen mit einer Wasseraufwandmenge von 'Compounds according to the invention were then prepared as aqueous suspensions or emulsions having a water application rate of '.
umgerechnet 600 l/ha in unterschiedlichen Dosierungen auf die Oberfläche der Abdeckerde appliziert.converted 600 l / ha in different dosages on the surface of the cover soil.
Nach der Behandlung wurden die Töpfe im Gewächshaus aufgestellt und unter guten Wachstumsbedingungen für dieAfter the treatment, the pots were placed in the greenhouse and under good growth conditions for the
Unkrautpflanzen gehalten (Temperatur 23 plus/minus 10C, relative Luftfeuchte 60-80%).Weed plants kept (temperature 23 plus / minus 1 0 C, relative humidity 60-80%).
Die optische Bonitur der Pflanzen- bzw. Auflaufschäden erfolgte nach dem Auflaufen der Versuchspflanzen nach einer VersuchszeitThe visual assessment of the plant damage or the emergence damage occurred after emergence of the test plants after a trial period
von 3-4 Wochen im Vergleich zu unbehandelten Kontrollen.of 3-4 weeks compared to untreated controls.
Die Boniturwerte in Tabelle 2 zeigen, daß die erfindungsgemäßen Verbindungen eine gute herbizide Vorauflaufwirksamkeit gegenThe rating values in Table 2 show that the compounds according to the invention have a good herbicidal pre-emergence activity against
ein breites Spektrum von Ungräsern und Unkräutern besitzen.have a broad spectrum of grass weeds and weeds.
Vorlaufwirkung der erfindungsgemäßen VerbindungenPreliminary action of the compounds of the invention
2. Unkrautwirkung im Nachauflauf2. weed effect postemergence
Samen bzw. Rhizomstücke von mono- und dikotylen Unkräutern wurden in Plastiktöpfen (0 = 9 cm) in sandigem Lehmboden ausgelegt, mit Erde abgedeckt und im Gewächshaus unter guten Wachstumsbedingungen angezogen. Drei Wochen nach der Aussaat wurden die Versuchspflanzen im Dreiblattstadium behandelt.Seeds or rhizome pieces of monocotyledonous and dicotyledonous weeds were placed in sandy loam soil in plastic pots (0 = 9 cm), covered with soil and grown in the greenhouse under good growth conditions. Three weeks after sowing, the test plants were treated at the trefoil stage.
Die als Spritzpulver bzw. als Emulsionskonzentrate formulierten erfindungsgemäßen Verbindungen wurden in verschiedenen Dosierungen mit einer Wasseraufwandmenge von umgerechnet 600 l/ha auf die grünen Pflanzenteile gesprüht und nach etwa 3-4 Wochen Standzeit der Versuchspflanzen im Gewächshaus unter optimalen Wachstumsbedingungen (Temperatur 23 plus/minus 10C, relative Luftfeuchte 60-80%) die Wirkung der Präparate optisch im Vergleich zu unbehandelten Kontrollen bonitiert. Die erfindungsgemäßen Verbindungen weisen auch im Nachlauf eine gute herbizide Wirksamkeit gegen ein breites Spektrum wirtschaftlich wichtiger Ungräser und Unkräuter auf.The compounds according to the invention formulated as wettable powders or emulsion concentrates were sprayed onto the green plant parts in various dosages with a conversion rate of 600 l / ha and after about 3-4 weeks life of the test plants in the greenhouse under optimum growth conditions (temperature 23 plus / minus 1 0 C, relative humidity 60-80%) scores the effect of the preparations visually compared to untreated controls. The compounds according to the invention also have a good herbicidal activity against a broad spectrum of economically important weeds and weeds in the wake.
Nachauflaufverfahren der erfindungsgemäßen VerbindungenPostemergence process of the compounds of the invention
Abkürzungen: siehe Tabelle 2Abbreviations: see Table 2
3. Kulturpflanzenverträglichkeit3. crop compatibility
In weiteren Versuchen im Gewächshaus wurden Samen einer größeren Anzahl von Kulturpflanzen in Topfen in sandigem Lehmboden ausgelegt und mit Erde abgedeckt.In further experiments in the greenhouse, seeds of a larger number of crops were placed in pots in sandy loam soil and covered with soil.
Ein Teil der Töpfe wurde sofort wie unter 1. beschrieben behandelt; die übrigen wurden im Gewächshaus aufgestellt, bis die Pflanzen zwei bis drei echte Blätter entwickelt hatten und dann mit den erfindungsgemäßen Substanzen in unterschiedlichen Dosierungen, wie unter 2. beschrieben, besprüht.Part of the pots were treated immediately as described under 1.; the remainder were set up in the greenhouse until the plants had developed two to three true leaves and then sprayed with the substances according to the invention in different dosages, as described under 2.
Vier bis fünf Wochen nach der Applikation und Standzeit im Gewächshaus wurde mittels optischer Bonitur festgestellt,*daß die erfindungsgemäßen Verbindungen zweikeimblättrige Kulturen wie z. B. Soja, Baumwolle, Raps, Zuckerrüben und Kartoffeln im Vor- und Nachauflaufverfahren selbst bei hohen Wirkstoffdosierungen ungeschädigt ließen. Einige Substanzen schonten darüber hinaus auch Graminen-Kulturen wie z. B. Gerste, Sorghum, Mais, Weizen oder Reis. Die Verbindungen der Formel I weisen somit eine hohe Selektivität bei Anwendung zur Bekämpfung von unerwünschtem Pflanzenwuchs in landwirtschaftlich wichtigen Kulturen auf.Four to five weeks after the application and life in the greenhouse was determined by optical Bonitur, * that the compounds of the invention dicotyledonous crops such. As soybean, cotton, oilseed rape, sugar beets and potatoes in pre- and post-emergence even at high doses of active ingredient undamaged. In addition, some substances also protected Graminen cultures such. As barley, sorghum, corn, wheat or rice. The compounds of the formula I thus have a high selectivity when used for controlling unwanted plant growth in agriculturally important crops.
Claims (1)
R11 = (C1-C12J-AIkYl, (C1-C4J-AIkOXy-(C1-C4)^IkYl, Phenoxy^-Cjalkyl, Benzyloxy^-QJalkyl,-OR 11 , -S (O) P R 11 , -NR 12 R 13 or -NH-NR 14 R 15 ,
R 11 = (C 1 -C 12 ) -alkyl, (C 1 -C 4 -alkoxy- (C 1 -C 4 ) -alkyl), phenoxy-C 1 -C -alkyl, benzyloxy -Q-alkyl,
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853533442 DE3533442A1 (en) | 1985-09-19 | 1985-09-19 | NEW 2-ARYL-4,5,6,7-TETRAHYDROISOINDOLINONE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE IN PLANT PROTECTION |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD252113A5 true DD252113A5 (en) | 1987-12-09 |
Family
ID=6281398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD86294528A DD252113A5 (en) | 1985-09-19 | 1986-09-18 | HERBICIDE MEDIUM |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0215424A3 (en) |
| JP (1) | JPS6270356A (en) |
| AU (1) | AU6292586A (en) |
| BR (1) | BR8604486A (en) |
| DD (1) | DD252113A5 (en) |
| DE (1) | DE3533442A1 (en) |
| ES (1) | ES2001790A6 (en) |
| GR (1) | GR862379B (en) |
| HU (1) | HUT43315A (en) |
| PL (1) | PL261454A1 (en) |
| ZA (1) | ZA867105B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3604599A1 (en) * | 1985-09-19 | 1987-03-26 | Hoechst Ag | NEW TETRAHYDROISOINDOLINONES, PROCESS FOR THEIR PRODUCTION AND THEIR USE IN PLANT PROTECTION |
| US4737512A (en) * | 1986-10-27 | 1988-04-12 | Warner-Lambert Company | 4-(substituted-isoindol-2-yl)phenoxy-pentanoic and -heptanoic acids and derivatives as anti-arteriosclerotic agents |
| US4816065A (en) * | 1986-12-23 | 1989-03-28 | Fmc Corporation | Herbicides |
| DE3819439A1 (en) * | 1988-06-08 | 1989-12-14 | Bayer Ag | SUBSTITUTED N-PHENYL NITROGEN HETEROCYCLES, METHODS AND SUBSTITUTED 2-FLUOR-5-ALKOXY-ANILINE AS INTERMEDIATE PRODUCTS FOR THEIR PRODUCTION, AND THEIR USE AS HERBICIDES AND PLANT GROWTH |
| EP0420810A3 (en) * | 1989-09-28 | 1992-01-15 | Ciba-Geigy Ag | Herbicidal agents |
| IT1245351B (en) * | 1991-03-19 | 1994-09-20 | Italfarmaco Spa | CARDIOVASCULAR ACTIVITY ISOINDLES |
| PL2961740T3 (en) * | 2013-02-28 | 2017-07-31 | Syngenta Participations Ag | Plant growth regulating compounds |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2831770A1 (en) * | 1977-07-22 | 1979-02-01 | Ciba Geigy Ag | N-Aryl-3-hydroxy-isoindolinone derivs. - with herbicidal, plant growth regulant and antifungal activity |
| US4292070A (en) * | 1979-04-13 | 1981-09-29 | Mitsubishi Chemical Industries, Ltd. | N-Substituted tetrahydrophthalimide and herbicidal composition |
| AU542544B2 (en) * | 1980-03-12 | 1985-02-28 | Nippon Kayaku Kabushiki Kaisha | Tetrahydrophthalimide derivatives |
| JPS56169669A (en) * | 1980-05-30 | 1981-12-26 | Takeda Chem Ind Ltd | Hexahydroisoindole derivative, its preparation and herbicide |
| US4536209A (en) * | 1980-10-07 | 1985-08-20 | Mitsubishi Chemical Industries Ltd. | N-(3-substituted oxyphenyl)tetrahydrophthalimides and herbicidal composition |
| US4439229A (en) * | 1981-06-29 | 1984-03-27 | Rohm And Haas Company | Substituted phthalimides herbicides |
| EP0095192B1 (en) * | 1982-05-26 | 1988-08-10 | Sumitomo Chemical Company, Limited | Tetrahydrophthalimides, and their production and use |
-
1985
- 1985-09-19 DE DE19853533442 patent/DE3533442A1/en not_active Withdrawn
-
1986
- 1986-09-09 EP EP86112460A patent/EP0215424A3/en not_active Withdrawn
- 1986-09-17 ES ES8601956A patent/ES2001790A6/en not_active Expired
- 1986-09-17 GR GR862379A patent/GR862379B/en unknown
- 1986-09-17 HU HU863977A patent/HUT43315A/en unknown
- 1986-09-18 DD DD86294528A patent/DD252113A5/en unknown
- 1986-09-18 JP JP61218256A patent/JPS6270356A/en active Pending
- 1986-09-18 PL PL1986261454A patent/PL261454A1/en unknown
- 1986-09-18 AU AU62925/86A patent/AU6292586A/en not_active Abandoned
- 1986-09-18 ZA ZA867105A patent/ZA867105B/en unknown
- 1986-09-19 BR BR8604486A patent/BR8604486A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR8604486A (en) | 1987-05-19 |
| ZA867105B (en) | 1987-04-29 |
| PL261454A1 (en) | 1988-03-03 |
| JPS6270356A (en) | 1987-03-31 |
| ES2001790A6 (en) | 1988-06-16 |
| EP0215424A3 (en) | 1987-05-27 |
| GR862379B (en) | 1987-01-16 |
| DE3533442A1 (en) | 1987-03-26 |
| EP0215424A2 (en) | 1987-03-25 |
| AU6292586A (en) | 1987-03-26 |
| HUT43315A (en) | 1987-10-28 |
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