DD259993A5 - Herbizide mittel - Google Patents

Herbizide mittel Download PDF

Info

Publication number: DD259993A5
Authority: DD; German Democratic Republic
Prior art keywords: alkyl; alkoxy; alkoxycarbonyl; substituted; halogen
Prior art date: 1986-02-08

Application number

DD87299756A

Other languages

German (de)

English (en)

Inventor

Rainer Liebl

Reinhard Handte

Hilmar Mildenberger

Kalus Bauer

Hermann Bieringer

Original Assignee

��@��k��

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1986-02-08

Filing date

1987-02-06

Publication date

1988-09-14

1987-02-06 Application filed by ��@��k�� filed Critical ��@��k��

1988-09-14 Publication of DD259993A5 publication Critical patent/DD259993A5/de

Links

230000002363 herbicidal effect Effects 0.000 title abstract description 13
239000004009 herbicide Substances 0.000 title abstract description 7
125000000217 alkyl group Chemical group 0.000 claims abstract description 36
150000001875 compounds Chemical class 0.000 claims abstract description 35
-1 (substituted) phenoxy Chemical group 0.000 claims abstract description 33
229910052736 halogen Chemical group 0.000 claims abstract description 22
150000002367 halogens Chemical group 0.000 claims abstract description 22
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
239000001257 hydrogen Substances 0.000 claims abstract description 22
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 16
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 15
125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
150000002431 hydrogen Chemical class 0.000 claims abstract description 9
239000001301 oxygen Substances 0.000 claims abstract description 9
229910052717 sulfur Chemical group 0.000 claims abstract description 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
239000011593 sulfur Chemical group 0.000 claims abstract description 6
125000005843 halogen group Chemical group 0.000 claims abstract description 5
125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 4
125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 3
125000002947 alkylene group Chemical group 0.000 claims abstract description 3
125000004465 cycloalkenyloxy group Chemical group 0.000 claims abstract description 3
239000000460 chlorine Substances 0.000 claims description 32
239000000203 mixture Substances 0.000 claims description 19
125000004438 haloalkoxy group Chemical group 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
239000000969 carrier Substances 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
125000001188 haloalkyl group Chemical group 0.000 claims description 3
125000005554 pyridyloxy group Chemical group 0.000 claims description 3
239000000080 wetting agent Substances 0.000 claims description 3
125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 1
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims 1
125000000392 cycloalkenyl group Chemical group 0.000 abstract description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
125000000753 cycloalkyl group Chemical group 0.000 abstract 2
101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 abstract 1
125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
125000005083 alkoxyalkoxy group Chemical group 0.000 abstract 1
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 abstract 1
125000006350 alkyl thio alkyl group Chemical group 0.000 abstract 1
230000009286 beneficial effect Effects 0.000 abstract 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
229910052799 carbon Inorganic materials 0.000 abstract 1
150000001721 carbon Chemical group 0.000 abstract 1
125000000000 cycloalkoxy group Chemical group 0.000 abstract 1
241000196324 Embryophyta Species 0.000 description 31
239000004480 active ingredient Substances 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
240000007594 Oryza sativa Species 0.000 description 12
230000000694 effects Effects 0.000 description 12
235000007164 Oryza sativa Nutrition 0.000 description 10
235000009566 rice Nutrition 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000013543 active substance Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 9
239000000126 substance Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000012279 sodium borohydride Substances 0.000 description 7
229910000033 sodium borohydride Inorganic materials 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
230000012010 growth Effects 0.000 description 6
239000000843 powder Substances 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
239000002689 soil Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
239000013078 crystal Substances 0.000 description 5
239000004495 emulsifiable concentrate Substances 0.000 description 5
238000009472 formulation Methods 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000005457 ice water Substances 0.000 description 5
238000002360 preparation method Methods 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
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
235000008504 concentrate Nutrition 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
239000000839 emulsion Substances 0.000 description 4
238000000034 method Methods 0.000 description 4
238000002156 mixing Methods 0.000 description 4
229920000151 polyglycol Polymers 0.000 description 4
239000010695 polyglycol Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
235000014113 dietary fatty acids Nutrition 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
239000000194 fatty acid Substances 0.000 description 3
229930195729 fatty acid Natural products 0.000 description 3
150000002191 fatty alcohols Chemical class 0.000 description 3
239000003337 fertilizer Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
210000000056 organ Anatomy 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
YDAOJBFHESDZBJ-UHFFFAOYSA-N 1-butyl-3-(4-chloro-2-fluoro-5-methoxyphenyl)-4-hydroxyimidazolidine-2-thione Chemical compound S=C1N(CCCC)CC(O)N1C1=CC(OC)=C(Cl)C=C1F YDAOJBFHESDZBJ-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
ULWXRDGAJFGKJQ-UHFFFAOYSA-N 3-(4-chloro-2-fluoro-5-methoxyphenyl)-4-hydroxy-1-methylimidazolidin-2-one Chemical compound C1=C(Cl)C(OC)=CC(N2C(N(C)CC2O)=O)=C1F ULWXRDGAJFGKJQ-UHFFFAOYSA-N 0.000 description 2
HBEXJYHCMJTELJ-UHFFFAOYSA-N 4-hydroxy-1-methyl-3-[3-methyl-4-(1,1,2,2-tetrafluoroethoxy)phenyl]imidazolidin-2-one Chemical compound O=C1N(C)CC(O)N1C1=CC=C(OC(F)(F)C(F)F)C(C)=C1 HBEXJYHCMJTELJ-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-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
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
235000021536 Sugar beet Nutrition 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
WVBJRVLRVQMLBB-UHFFFAOYSA-N [3-(4-chloro-2-fluoro-5-methoxyphenyl)-1-methyl-2-oxoimidazolidin-4-yl] n-methylcarbamate Chemical compound CNC(=O)OC1CN(C)C(=O)N1C1=CC(OC)=C(Cl)C=C1F WVBJRVLRVQMLBB-UHFFFAOYSA-N 0.000 description 2
RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 2
235000012211 aluminium silicate Nutrition 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
239000002270 dispersing agent Substances 0.000 description 2
239000000945 filler Substances 0.000 description 2
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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
239000012280 lithium aluminium hydride Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
230000008635 plant growth Effects 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
239000004033 plastic Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000009331 sowing Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000454 talc Substances 0.000 description 2
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230000009105 vegetative growth Effects 0.000 description 2
238000009736 wetting Methods 0.000 description 2
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 description 1
ADQMNCSWLZUGMI-UHFFFAOYSA-N 1-butyl-3-(4-chloro-2-fluoro-5-methoxyphenyl)-2-sulfanylideneimidazolidin-4-one Chemical compound S=C1N(CCCC)CC(=O)N1C1=CC(OC)=C(Cl)C=C1F ADQMNCSWLZUGMI-UHFFFAOYSA-N 0.000 description 1
BNNAICMDBVTUDS-UHFFFAOYSA-N 1-methyl-3-[3-methyl-4-(1,1,2,2-tetrafluoroethoxy)phenyl]-4-phenylmethoxyimidazolidin-2-one Chemical compound C=1C=C(OC(F)(F)C(F)F)C(C)=CC=1N1C(=O)N(C)CC1OCC1=CC=CC=C1 BNNAICMDBVTUDS-UHFFFAOYSA-N 0.000 description 1
XYCMJEAXVSFTPM-UHFFFAOYSA-N 1-methyl-3-[3-methyl-4-(1,1,2,2-tetrafluoroethoxy)phenyl]imidazolidine-2,4-dione Chemical compound O=C1N(C)CC(=O)N1C1=CC=C(OC(F)(F)C(F)F)C(C)=C1 XYCMJEAXVSFTPM-UHFFFAOYSA-N 0.000 description 1
XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
RVPMRUPULSFXAA-UHFFFAOYSA-N 2-(4-chloro-2-fluoro-5-methoxyphenyl)-1-hydroxy-1,5,6,7,8,8a-hexahydroimidazo[1,5-a]pyridin-3-one Chemical compound C1=C(Cl)C(OC)=CC(N2C(N3CCCCC3C2O)=O)=C1F RVPMRUPULSFXAA-UHFFFAOYSA-N 0.000 description 1
UUECXRTWFFUGFL-UHFFFAOYSA-N 2-(4-chloro-2-fluoro-5-methoxyphenyl)-3-sulfanylidene-6,7,8,8a-tetrahydro-5h-imidazo[1,5-a]pyridin-1-one Chemical compound C1=C(Cl)C(OC)=CC(N2C(N3CCCCC3C2=O)=S)=C1F UUECXRTWFFUGFL-UHFFFAOYSA-N 0.000 description 1
JESDAUZJNITYAX-UHFFFAOYSA-N 2-(4-chloro-2-fluoro-5-methoxyphenyl)-6,7,8,8a-tetrahydro-5h-imidazo[1,5-a]pyridine-1,3-dione Chemical compound C1=C(Cl)C(OC)=CC(N2C(N3CCCCC3C2=O)=O)=C1F JESDAUZJNITYAX-UHFFFAOYSA-N 0.000 description 1
QZAQOFCMLDWELA-UHFFFAOYSA-N 3-(4-chloro-2-fluoro-5-methoxyphenyl)-1-methylimidazolidine-2,4-dione Chemical compound C1=C(Cl)C(OC)=CC(N2C(N(C)CC2=O)=O)=C1F QZAQOFCMLDWELA-UHFFFAOYSA-N 0.000 description 1
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WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
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239000007900 aqueous suspension Substances 0.000 description 1
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SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
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125000001246 bromo group Chemical group Br* 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
WQJONRMBVKFKOB-UHFFFAOYSA-N cyanatosulfanyl cyanate Chemical compound N#COSOC#N WQJONRMBVKFKOB-UHFFFAOYSA-N 0.000 description 1
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YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical group O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
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150000007529 inorganic bases Chemical class 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000003621 irrigation water Substances 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
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
230000007170 pathology Effects 0.000 description 1
230000000149 penetrating effect Effects 0.000 description 1
230000035479 physiological effects, processes and functions Effects 0.000 description 1
HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical class OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 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
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
238000001556 precipitation Methods 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
239000007858 starting material Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
230000036435 stunted growth Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 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
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/40—Two or more oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/42—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

DD87299756A 1986-02-08 1987-02-06 Herbizide mittel DD259993A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19863604042 DE3604042A1 (de)	1986-02-08	1986-02-08	Imidazolidin(thi)on-derivate, verfahren zu ihrer herstellung sowie ihre verwendung im pflanzenschutz

Publications (1)

Publication Number	Publication Date
DD259993A5 true DD259993A5 (de)	1988-09-14

Family

ID=6293731

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87299756A DD259993A5 (de)	1986-02-08	1987-02-06	Herbizide mittel

Country Status (13)

Country	Link
US (1)	US4749403A (da)
EP (1)	EP0234323A1 (da)
JP (1)	JPS62192363A (da)
CN (1)	CN87100616A (da)
AU (1)	AU6859287A (da)
BR (1)	BR8700551A (da)
DD (1)	DD259993A5 (da)
DE (1)	DE3604042A1 (da)
DK (1)	DK61987A (da)
HU (1)	HUT43317A (da)
IL (1)	IL81491A0 (da)
PT (1)	PT84259A (da)
ZA (1)	ZA87869B (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0355599A1 (de) *	1988-08-20	1990-02-28	Bayer Ag	3-Aryl-pyrrolidin-2,4-dione

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3819439A1 (de) *	1988-06-08	1989-12-14	Bayer Ag	Substituierte n-phenyl-stickstoffheterocyclen, verfahren sowie substituierte 2-fluor-5-alkoxy-aniline als zwischenprodukte zu deren herstellung, und ihre verwendung als herbizide und pflanzenwuchsregulatoren
JP2860367B2 (ja) *	1989-03-02	1999-02-24	アグロカネショウ株式会社	複素環化合物、その製造法及びそれを有効成分として含有する除草剤
US4985065A (en) *	1989-05-10	1991-01-15	Fmc Corporation	Tetrazolinone herbicides
US4956004A (en) *	1989-05-10	1990-09-11	Fmc Corporation	Herbicidal triazinediones
US5411981A (en) *	1991-01-09	1995-05-02	Roussel Uclaf	Phenylimidazolidines having antiandrogenic activity
USRE35956E (en) *	1991-01-09	1998-11-10	Roussel Uclaf	Phenylimidazolidines having antiandrogenic activity
US5821372A (en) *	1995-11-28	1998-10-13	American Home Products Corporation	2-thioxo-imidazolidin-4-one derivatives
TW418195B (en) *	1995-11-28	2001-01-11	American Home Prod	2-thioxo-imidazolidin-4-one derivatives
US5663363A (en) *	1996-11-21	1997-09-02	American Home Products Corporation	2-thioxo-imidazolidin-4-one derivatives
US7718684B2 (en) *	2004-02-24	2010-05-18	The Regents Of The University Of California	Methods and materials for assessing prostate cancer therapies and compounds
US7709517B2 (en) *	2005-05-13	2010-05-04	The Regents Of The University Of California	Diarylhydantoin compounds
EP2656842B1 (en)	2006-03-27	2016-08-10	The Regents of The University of California	Androgen receptor modulator for the treatment of prostate cancer and androgen receptor-associated diseases
WO2007127010A2 (en) *	2006-03-29	2007-11-08	The Regents Of The University Of California	Diarylthiohydantoin compounds
CA2966280A1 (en)	2007-10-26	2009-04-30	The Regents Of The University Of California	Diarylhydantoin compounds
HUE037389T2 (hu)	2010-02-16	2018-08-28	Aragon Pharmaceuticals Inc	Androgén receptor modulátorok és alkalmazásaik
ES2836424T3 (es)	2012-09-26	2021-06-25	Aragon Pharmaceuticals Inc	Antiandrógenos para tratar el cáncer de próstata no metastásico y resistente a la castración
CA3105575A1 (en)	2013-01-15	2014-07-24	Aragon Pharmaceuticals, Inc.	Androgen receptor modulator and uses thereof
UA118035C2 (uk) *	2013-10-07	2018-11-12	Сінгента Партісіпейшнс Аг	Гербіцидні сполуки
TWI726969B (zh)	2016-01-11	2021-05-11	比利時商健生藥品公司	用作雄性激素受體拮抗劑之經取代之硫尿囊素衍生物
UA129105C2 (uk)	2017-10-16	2025-01-15	Арагон Фармасьютикалз, Інк.	Антиандрогени для лікування неметастатичного резистентного до кастрації раку передміхурової залози

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2658058A1 (de) *	1976-12-22	1978-07-06	Bayer Ag	Substituierte 4,5-dihydroxythiazolidine, ein verfahren zu ihrer herstellung sowie ihre verwendung als ektoparasitizide
US4179276A (en) *	1977-02-01	1979-12-18	E. I. Du Pont De Nemours And Company	Novel imidazothiazine-1,3 (2H)-diones
DK156573C (da) *	1981-06-16	1990-01-29	Sumitomo Chemical Co	2-(2-fluor-4-halogen-5-substitueret-phenyl)-hydantoinderivater, et herbicidt praeparat indeholdende disse, en fremgangsmaade til bekaempelse af ukrudt under anvendelse af disse samt anvendelse af disse som herbicid
US4578107A (en) *	1982-09-27	1986-03-25	Otsuka Kagaku Kabushiki Kaisha	Herbicidal imidazolidine-2-one derivatives

1986
- 1986-02-08 DE DE19863604042 patent/DE3604042A1/de not_active Withdrawn
1987
- 1987-01-29 EP EP87101242A patent/EP0234323A1/de not_active Withdrawn
- 1987-02-06 ZA ZA87869A patent/ZA87869B/xx unknown
- 1987-02-06 IL IL81491A patent/IL81491A0/xx unknown
- 1987-02-06 DD DD87299756A patent/DD259993A5/de not_active IP Right Cessation
- 1987-02-06 JP JP62024949A patent/JPS62192363A/ja active Pending
- 1987-02-06 AU AU68592/87A patent/AU6859287A/en not_active Abandoned
- 1987-02-06 HU HU87480A patent/HUT43317A/hu unknown
- 1987-02-06 BR BR8700551A patent/BR8700551A/pt unknown
- 1987-02-06 US US07/011,780 patent/US4749403A/en not_active Expired - Fee Related
- 1987-02-06 DK DK061987A patent/DK61987A/da not_active Application Discontinuation
- 1987-02-07 CN CN198787100616A patent/CN87100616A/zh active Pending
- 1987-02-09 PT PT84259A patent/PT84259A/pt unknown

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0355599A1 (de) *	1988-08-20	1990-02-28	Bayer Ag	3-Aryl-pyrrolidin-2,4-dione

Also Published As

Publication number	Publication date
DE3604042A1 (de)	1987-08-13
AU6859287A (en)	1987-08-13
IL81491A0 (en)	1987-09-16
ZA87869B (en)	1987-09-30
DK61987A (da)	1987-08-09
US4749403A (en)	1988-06-07
HUT43317A (en)	1987-10-28
CN87100616A (zh)	1987-08-19
PT84259A (en)	1987-03-01
BR8700551A (pt)	1987-12-08
DK61987D0 (da)	1987-02-06
EP0234323A1 (de)	1987-09-02
JPS62192363A (ja)	1987-08-22

Legal Events

Date	Code	Title	Description
1996-05-23	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD259993A5 (de)	1988-09-14	Herbizide mittel
EP0007990B1 (de)	1981-03-25	Pyrazolätherderivate, Verfahren zu ihrer Herstellung und Herbizide, die diese Verbindungen enthalten
EP0342569B1 (de)	1994-06-22	Heterocyclische 2-Alkoxyphenoxysulfonylharnstoffe und ihre Verwendung als Herbizide oder Pflanzenwachstumsregulatoren
EP0003805B1 (de)	1982-06-30	Pyridazonverbindungen und diese enthaltende herbizide Zusammensetzungen
EP0272594A1 (de)	1988-06-29	Bicyclische Imide, Verfahren zu ihrer Herstellung sowie ihre Verwendung im Pflanzenschutz
DD218544A5 (de)	1985-02-13	Herbizide mittel
DE3131489A1 (de)	1983-02-24	Heterocyclisch substituierte sulfonylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung in der landwirtschaft
EP0264865A2 (de)	1988-04-27	Alpha-Iminocarbonsäureanilide enthaltende herbizide Mittel sowie neue Alpha-Iminocarbonsäureanilide und Verfahren zu ihrer Herstellung
EP0075840B1 (de)	1987-11-11	Heterocyclische Phenyläther, Verfahren zu deren Herstellung und diese enthaltende herbizide Mittel
EP0196026B1 (de)	1989-05-31	Phosphorhaltige funktionelle Essigsäurederivate, Verfahren zu ihrer Herstellung und sie enthaltende herbizide, wachstumsregulierende Mittel
DE3533440A1 (de)	1987-03-26	N-substituierte 3,4,5,6-tetrahydrophthalimide, verfahren zu ihrer herstellung sowie ihre verwendung im pflanzenschutz
EP0342568B1 (de)	1994-02-02	Heterocyclisch substituierte Phenoxysulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide oder Pflanzenwachstumsregulatoren
DD273436A5 (de)	1989-11-15	Verfahren zur herstellung substituierter tetrahydrophtholimide und ihre verwendung der herbezide
EP0053699A1 (de)	1982-06-16	2'-Phenylhydrazino-2-cyanacrylsäureester und diese enthaltende Herbizide
EP0058639B1 (de)	1985-08-14	2-(4-(6-Halogen-chinoxalinyl-2-oxy)-phenoxy)-propionsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Herbizide und Pflanzenwuchsregulatoren
DE3533442A1 (de)	1987-03-26	Neue 2-aryl-4,5,6,7-tetrahydroisoindolinone, verfahren zu ihrer herstellung sowie ihre verwendung im pflanzenschutz
EP0319689B1 (de)	1993-12-15	Heterocyclisch substituierte N-Sultam-sulfonamide, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DD218268A5 (de)	1985-02-06	Herbizide zusammensetzung
EP0069244A1 (de)	1983-01-12	Verfahren zur Beeinflussung des Pflanzenwachstums
EP0303114A2 (de)	1989-02-15	Heterocyclisch substituierte Sulfamidsäurephenylester, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DE3807532A1 (de)	1989-09-21	Pyrimidin-carbonsaeuren, verfahren zur herstellung und ihre verwendung als herbizide
DE3502629A1 (de)	1986-07-31	Phenoxybenzoesaeurederivate, verfahren zu ihrer herstellung sowie ihre verwendung im pflanzenschutz
DE3816994A1 (de)	1989-11-30	Herbizide mittel auf der basis von 4-hydroxypyrimidin-derivaten
EP0009555A1 (de)	1980-04-16	Herbizide Mittel auf der Basis eines Thiolcarbamats, die Halogenacylamide als Antagonisten enthalten, und ihre Verwendung in einem Verfahren zur selektiven Bekämpfung von unerwünschtem Pflanzenwuchs
EP0221439A1 (de)	1987-05-13	Herbizide Mittel, die stickstoffhaltige Heterocyclen mit Arylcarbamoyl-Resten enthalten, sowie neue heterocyclische Derivate mit Arylcarbamoyl-Resten

DD259993A5 - Herbizide mittel - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (1)

Publications (1)

Family

ID=6293731

Family Applications (1)

Country Status (13)

Cited By (1)

Families Citing this family (20)

Family Cites Families (4)

Cited By (1)

Also Published As

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