DD146540A5 - Herbizides mittel - Google Patents

Herbizides mittel Download PDF

Info

Publication number: DD146540A5
Authority: DD; German Democratic Republic
Prior art keywords: ester; acid; phenyl; alkyl; phenylj
Prior art date: 1978-10-12

Application number

DD79216084A

Other languages

German (de)

English (en)

Inventor

Gerhard Boroschewski

Ludwig Nuesslein

Friedrich Arndt

Original Assignee

Schering Ag

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.)

1978-10-12

Filing date

1979-10-08

Publication date

1981-02-18

1979-10-08 Application filed by Schering Ag filed Critical Schering Ag

1981-02-18 Publication of DD146540A5 publication Critical patent/DD146540A5/de

Links

239000004009 herbicide Substances 0.000 title abstract description 5
-1 methoxy-substituted phenyl Chemical group 0.000 claims abstract description 86
239000000203 mixture Substances 0.000 claims abstract description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
230000002363 herbicidal effect Effects 0.000 claims abstract description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
229910052736 halogen Inorganic materials 0.000 claims abstract description 4
125000005843 halogen group Chemical group 0.000 claims abstract 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
239000000969 carrier Substances 0.000 claims description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 claims description 2
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
125000004093 cyano group Chemical group *C#N 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
125000006000 trichloroethyl group Chemical group 0.000 claims 1
239000002253 acid Substances 0.000 abstract description 25
239000003795 chemical substances by application Substances 0.000 abstract description 8
239000004480 active ingredient Substances 0.000 abstract description 5
238000001228 spectrum Methods 0.000 abstract description 4
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 abstract description 2
101100072620 Streptomyces griseus ind2 gene Proteins 0.000 abstract 2
150000002148 esters Chemical class 0.000 description 46
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 31
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
150000001875 compounds Chemical class 0.000 description 19
239000000243 solution Substances 0.000 description 16
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 10
241000196324 Embryophyta Species 0.000 description 10
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
238000003756 stirring Methods 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 6
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 5
235000011331 Brassica Nutrition 0.000 description 5
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
235000002634 Solanum Nutrition 0.000 description 5
241000207763 Solanum Species 0.000 description 5
238000001816 cooling Methods 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
239000002904 solvent Substances 0.000 description 5
WIEVFFASDSZFMD-UHFFFAOYSA-N 2-cyanoethyl(phenyl)carbamic acid Chemical compound N#CCCN(C(=O)O)C1=CC=CC=C1 WIEVFFASDSZFMD-UHFFFAOYSA-N 0.000 description 4
CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 4
241000219198 Brassica Species 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000000654 additive Substances 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
238000000034 method Methods 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
229940051881 anilide analgesics and antipyretics Drugs 0.000 description 3
238000009835 boiling Methods 0.000 description 3
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
YXSKGOCVSTWEJU-UHFFFAOYSA-N n-(3-hydroxyphenyl)propanamide Chemical compound CCC(=O)NC1=CC=CC(O)=C1 YXSKGOCVSTWEJU-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000007787 solid Substances 0.000 description 3
229940018563 3-aminophenol Drugs 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
150000003931 anilides Chemical class 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
230000006378 damage Effects 0.000 description 2
UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
239000003921 oil Substances 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000000047 product Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 description 1
125000006727 (C1-C6) alkenyl group Chemical group 0.000 description 1
ONPGFTVBLFAILH-DUXPYHPUSA-N (e)-n-(3-hydroxyphenyl)but-2-enamide Chemical compound C\C=C\C(=O)NC1=CC=CC(O)=C1 ONPGFTVBLFAILH-DUXPYHPUSA-N 0.000 description 1
NUBKYCCXDNYHLQ-UHFFFAOYSA-N 2,2-dimethylpentanoyl chloride Chemical compound CCCC(C)(C)C(Cl)=O NUBKYCCXDNYHLQ-UHFFFAOYSA-N 0.000 description 1
FXKCXGBBUBCRPU-GBOPCIDUSA-N 2-[(2r,4ar,8s,8ar)-8-hydroxy-4a,8-dimethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]prop-2-enoic acid Chemical compound C1C[C@@H](C(=C)C(O)=O)C[C@H]2[C@@](C)(O)CCC[C@@]21C FXKCXGBBUBCRPU-GBOPCIDUSA-N 0.000 description 1
KAXCEFLQAYFJKV-UHFFFAOYSA-N 2-anilinoacetonitrile Chemical compound N#CCNC1=CC=CC=C1 KAXCEFLQAYFJKV-UHFFFAOYSA-N 0.000 description 1
125000005999 2-bromoethyl group Chemical group 0.000 description 1
ZAMRCGQXJHTHHA-UHFFFAOYSA-N 2-chloroethyl(phenyl)carbamic acid Chemical compound ClCCN(C(=O)O)C1=CC=CC=C1 ZAMRCGQXJHTHHA-UHFFFAOYSA-N 0.000 description 1
PZJFPNCBZDYKMJ-UHFFFAOYSA-N 2-cyanoethyl-(3-methylphenyl)carbamic acid Chemical compound C(#N)CCN(C(O)=O)C1=CC(=CC=C1)C PZJFPNCBZDYKMJ-UHFFFAOYSA-N 0.000 description 1
JWIUGHDRROUKJY-UHFFFAOYSA-N 2-cyanoethyl-(4-methylphenyl)carbamic acid Chemical compound CC1=CC=C(C=C1)N(CCC#N)C(O)=O JWIUGHDRROUKJY-UHFFFAOYSA-N 0.000 description 1
RLCNIFASNGVYMF-UHFFFAOYSA-N 2-ethoxyethyl(phenyl)carbamic acid Chemical compound CCOCCN(C(O)=O)C1=CC=CC=C1 RLCNIFASNGVYMF-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
NVAYCFVXLGWWCD-UHFFFAOYSA-N 2-hydroxyethyl(phenyl)carbamic acid Chemical compound OCCN(C(O)=O)C1=CC=CC=C1 NVAYCFVXLGWWCD-UHFFFAOYSA-N 0.000 description 1
QGHFBLVFNUYCSV-UHFFFAOYSA-N 2-methoxyethyl(phenyl)carbamic acid Chemical compound COCCN(C(O)=O)C1=CC=CC=C1 QGHFBLVFNUYCSV-UHFFFAOYSA-N 0.000 description 1
PFDJIMKTGBPMEC-UHFFFAOYSA-N 2-methylpropylcarbamic acid Chemical compound CC(C)CNC(O)=O PFDJIMKTGBPMEC-UHFFFAOYSA-N 0.000 description 1
JSIAIROWMJGMQZ-UHFFFAOYSA-N 2h-triazol-4-amine Chemical class NC1=CNN=N1 JSIAIROWMJGMQZ-UHFFFAOYSA-N 0.000 description 1
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241000743339 Agrostis Species 0.000 description 1
241000234282 Allium Species 0.000 description 1
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239000005995 Aluminium silicate Substances 0.000 description 1
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241001377087 Amsinckia Species 0.000 description 1
244000277177 Anchusa azurea Species 0.000 description 1
235000017106 Anchusa azurea Nutrition 0.000 description 1
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
241000219305 Atriplex Species 0.000 description 1
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
241000220243 Brassica sp. Species 0.000 description 1
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244000098897 Chenopodium botrys Species 0.000 description 1
235000005490 Chenopodium botrys Nutrition 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
235000007516 Chrysanthemum Nutrition 0.000 description 1
240000005250 Chrysanthemum indicum Species 0.000 description 1
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240000001879 Digitalis lutea Species 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
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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 1
QNVBIDULDLPCDQ-UHFFFAOYSA-N Ilicic acid Natural products CC1(O)CCC2(C)CCC(CC2C1)C(=C)C(=O)O QNVBIDULDLPCDQ-UHFFFAOYSA-N 0.000 description 1
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
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CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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SYZLRWKFUVSGCH-UHFFFAOYSA-N [3-(propanoylamino)phenyl] N-methyl-N-phenylcarbamate Chemical compound C(CC)(=O)NC=1C=C(C=CC1)OC(N(C1=CC=CC=C1)C)=O SYZLRWKFUVSGCH-UHFFFAOYSA-N 0.000 description 1
ILZLKUFTMSDABQ-UHFFFAOYSA-N [3-[(2,2,2-trichloroacetyl)amino]phenyl] carbonochloridate Chemical compound ClC(=O)OC1=CC=CC(NC(=O)C(Cl)(Cl)Cl)=C1 ILZLKUFTMSDABQ-UHFFFAOYSA-N 0.000 description 1
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IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
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RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
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OGQITOIUNAYOAX-UHFFFAOYSA-N ethyl-(2-ethylphenyl)carbamic acid Chemical compound CCN(C(O)=O)C1=CC=CC=C1CC OGQITOIUNAYOAX-UHFFFAOYSA-N 0.000 description 1
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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 1
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CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
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RGSXNBKIMXWTIA-UHFFFAOYSA-N n-(3-hydroxyphenyl)-2-methylpropanamide Chemical compound CC(C)C(=O)NC1=CC=CC(O)=C1 RGSXNBKIMXWTIA-UHFFFAOYSA-N 0.000 description 1
BZSAIZDIEYYOBA-UHFFFAOYSA-N n-(3-hydroxyphenyl)cyclopropanecarboxamide Chemical compound OC1=CC=CC(NC(=O)C2CC2)=C1 BZSAIZDIEYYOBA-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000002547 new drug Substances 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
231100001184 nonphytotoxic Toxicity 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
210000002741 palatine tonsil Anatomy 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
OLTPKMBOLARPFC-UHFFFAOYSA-N phenyl(2-phenylethyl)carbamic acid Chemical compound C=1C=CC=CC=1N(C(=O)O)CCC1=CC=CC=C1 OLTPKMBOLARPFC-UHFFFAOYSA-N 0.000 description 1
239000004476 plant protection product Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003560 thiocarbamic acids Chemical class 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
- 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
- A01N47/22—O-Aryl or S-Aryl esters 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

Landscapes

Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Environmental Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Plant Pathology (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

DD79216084A 1978-10-12 1979-10-08 Herbizides mittel DD146540A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19782844811 DE2844811A1 (de)	1978-10-12	1978-10-12	Carbaminsaeurephenylester, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes herbizides mittel

Publications (1)

Publication Number	Publication Date
DD146540A5 true DD146540A5 (de)	1981-02-18

Family

ID=6052188

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79216084A DD146540A5 (de)	1978-10-12	1979-10-08	Herbizides mittel

Country Status (33)

Country	Link
JP (1)	JPS5817744B2 (cs)
AR (1)	AR223188A1 (cs)
AT (1)	AT368360B (cs)
AU (1)	AU522297B2 (cs)
BE (1)	BE879388A (cs)
BR (1)	BR7906612A (cs)
CA (1)	CA1124251A (cs)
CH (1)	CH641768A5 (cs)
CS (1)	CS208137B2 (cs)
DD (1)	DD146540A5 (cs)
DE (1)	DE2844811A1 (cs)
EG (1)	EG13844A (cs)
ES (1)	ES484478A1 (cs)
FI (1)	FI792941A7 (cs)
FR (1)	FR2438648A1 (cs)
GB (1)	GB2033383B (cs)
GR (1)	GR74033B (cs)
HU (1)	HU185779B (cs)
IL (1)	IL58420A (cs)
IN (1)	IN153182B (cs)
IT (1)	IT1162589B (cs)
MA (1)	MA18607A1 (cs)
MX (1)	MX5735E (cs)
NL (1)	NL7906019A (cs)
PH (1)	PH15549A (cs)
PL (1)	PL119533B1 (cs)
PT (1)	PT70232A (cs)
RO (1)	RO79322A (cs)
SE (1)	SE7908273L (cs)
SU (1)	SU1083906A3 (cs)
TR (1)	TR20602A (cs)
YU (1)	YU204979A (cs)
ZA (1)	ZA795472B (cs)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2844806A1 (de) *	1978-10-11	1980-04-24	Schering Ag	Carbanilsaeure- eckige klammer auf 3-(alkylcarbonylamino)-phenyl eckige klammer zu -ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes herbizides mittel
EP0051564A1 (de) *	1980-10-31	1982-05-12	Ciba-Geigy Ag	Neue Carbamate
AU7645298A (en) *	1997-04-21	1998-11-13	Novartis Ag	Novel herbicides

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3865867A (en) *	1967-06-19	1975-02-11	Monsanto Co	Meta-bifunctional benzenes
CA975775A (en) *	1969-03-12	1975-10-07	Eugene G. Teach	Bromoacetanilides and their utility as biocides
FR2210186A5 (en) *	1972-12-13	1974-07-05	Rhone Progil	Halogenated ureidophenyl carbamates - herbicides, by reacting corresp. halophenols and isocyanates

1978
- 1978-10-12 DE DE19782844811 patent/DE2844811A1/de not_active Withdrawn
1979
- 1979-08-06 NL NL7906019A patent/NL7906019A/nl not_active Application Discontinuation
- 1979-08-21 YU YU02049/79A patent/YU204979A/xx unknown
- 1979-09-14 IN IN644/DEL/79A patent/IN153182B/en unknown
- 1979-09-21 FI FI792941A patent/FI792941A7/fi not_active Application Discontinuation
- 1979-09-26 ES ES484478A patent/ES484478A1/es not_active Expired
- 1979-09-26 PT PT70232A patent/PT70232A/pt unknown
- 1979-09-27 MX MX798406U patent/MX5735E/es unknown
- 1979-09-28 TR TR20602A patent/TR20602A/xx unknown
- 1979-10-01 GB GB7933946A patent/GB2033383B/en not_active Expired
- 1979-10-02 MA MA18807A patent/MA18607A1/fr unknown
- 1979-10-05 SE SE7908273A patent/SE7908273L/xx not_active Application Discontinuation
- 1979-10-08 DD DD79216084A patent/DD146540A5/de unknown
- 1979-10-09 IL IL58420A patent/IL58420A/xx unknown
- 1979-10-10 PL PL1979218851A patent/PL119533B1/pl unknown
- 1979-10-10 CH CH911579A patent/CH641768A5/de not_active IP Right Cessation
- 1979-10-10 GR GR60230A patent/GR74033B/el unknown
- 1979-10-10 EG EG593/79A patent/EG13844A/xx active
- 1979-10-11 BR BR7906612A patent/BR7906612A/pt unknown
- 1979-10-11 AT AT0664579A patent/AT368360B/de not_active IP Right Cessation
- 1979-10-11 SU SU792824354A patent/SU1083906A3/ru active
- 1979-10-11 FR FR7925313A patent/FR2438648A1/fr active Granted
- 1979-10-11 AU AU51684/79A patent/AU522297B2/en not_active Ceased
- 1979-10-11 CA CA337,402A patent/CA1124251A/en not_active Expired
- 1979-10-11 IT IT26401/79A patent/IT1162589B/it active
- 1979-10-11 RO RO7998910A patent/RO79322A/ro unknown
- 1979-10-11 HU HU79SCHE696A patent/HU185779B/hu unknown
- 1979-10-12 PH PH23165A patent/PH15549A/en unknown
- 1979-10-12 BE BE0/197628A patent/BE879388A/fr not_active IP Right Cessation
- 1979-10-12 AR AR278479A patent/AR223188A1/es active
- 1979-10-12 CS CS796953A patent/CS208137B2/cs unknown
- 1979-10-12 JP JP54130948A patent/JPS5817744B2/ja not_active Expired
- 1979-10-12 ZA ZA00795472A patent/ZA795472B/xx unknown

Also Published As

Publication number	Publication date
ATA664579A (de)	1982-02-15
RO79322A (ro)	1982-08-17
MX5735E (es)	1984-01-25
CH641768A5 (de)	1984-03-15
EG13844A (en)	1982-09-30
IT7926401A0 (it)	1979-10-11
HU185779B (en)	1985-03-28
BE879388A (fr)	1980-04-14
MA18607A1 (fr)	1980-07-01
YU204979A (en)	1983-04-30
SU1083906A3 (ru)	1984-03-30
JPS5817744B2 (ja)	1983-04-09
PL119533B1 (en)	1982-01-30
PT70232A (de)	1979-10-01
IL58420A0 (en)	1980-01-31
CA1124251A (en)	1982-05-25
AR223188A1 (es)	1981-07-31
GB2033383B (en)	1983-05-11
ES484478A1 (es)	1980-05-16
CS208137B2 (en)	1981-08-31
IN153182B (cs)	1984-06-09
IL58420A (en)	1984-05-31
FI792941A7 (fi)	1981-01-01
AU5168479A (en)	1980-04-17
DE2844811A1 (de)	1980-09-04
NL7906019A (nl)	1980-04-15
PL218851A1 (cs)	1980-07-28
FR2438648A1 (fr)	1980-05-09
AT368360B (de)	1982-10-11
FR2438648B1 (cs)	1983-09-16
AU522297B2 (en)	1982-05-27
TR20602A (tr)	1982-01-01
JPS5559158A (en)	1980-05-02
ZA795472B (en)	1980-09-24
GR74033B (cs)	1984-06-06
SE7908273L (sv)	1980-04-13
GB2033383A (en)	1980-05-21
PH15549A (en)	1983-02-09
BR7906612A (pt)	1980-06-17
IT1162589B (it)	1987-04-01

Publication	Publication Date	Title
EP0398072B1 (de)	1995-02-01	Aminosäureamid-Derivate
DE3334455A1 (de)	1984-09-06	Guanidin - derivate
DE3618662A1 (de)	1987-12-10	Trisubstituierte 1,3,5-triazin-2,4,6-trione
DE2909991A1 (de)	1980-10-02	1,2,3-thiadiazol-5-carbonsaeurederivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit herbizider und wuchsregulatorischer sowie fungizider wirkung
DD224760A5 (de)	1985-07-17	Herbizide mittel
EP0000051B1 (de)	1980-09-17	N-acylmethyl-chloroacetanilide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Herbizide.
DD146540A5 (de)	1981-02-18	Herbizides mittel
EP0013429B1 (de)	1983-07-20	Vorlauf- und Nachlauf-Herbizide, deren aktive Substanz ein N-(Trimethyl-cyclohexen-1-yl)-N-isopropy-alpha-chloracetamid ist
US4344790A (en)	1982-08-17	Carbaminic acid esters with herbicidal properties
CH628615A5 (de)	1982-03-15	Verfahren zur herstellung von neuen n-chloracetyl-n-phenyl-alaninestern.
EP0010715B1 (de)	1982-01-27	Neue, eine Oximgruppe enthaltende N-Alkylhalogenacetanilide, Verfahren zu ihrer Herstellung, sie enthaltende herbizide Mittel, ein Verfahren zur Bekämpfung von Unkräutern und ein Verfahren zur Herstellung von herbiziden Mitteln.
EP0065712A2 (de)	1982-12-01	N-(1-Alkenyl)-chloressigsäureanilide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DE3431920A1 (de)	1986-03-13	Substituierte carbonylphenylsulfonylguanidine
DE2803662A1 (de)	1979-07-26	Chloracetanilide, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel
DE2856651C2 (cs)	1989-06-22
DE1027930B (de)	1958-04-10	Mittel zur Bekaempfung unerwuenschten Pflanzenwuchses
DE2320362A1 (de)	1974-11-07	Dichlorthiazolylharnstoffe, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide
DE2843691A1 (de)	1980-04-24	Diurethane, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel
EP0032366B1 (de)	1983-09-07	Verwendung von 4-Thioparabansäure-Derivaten als herbizide Wirkstoffe
CH645344A5 (de)	1984-09-28	N-(2-propinyl)-carbanilsaeure-(3-methoxycarbonylaminophenyl)-ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel.
DE2608473A1 (de)	1977-09-01	N-methylcarbanilsaeure- eckige klammer auf 3-(aethoxycarbonylamino)-phenyl eckige klammer zu -ester als baumwollherbizides mittel
EP0071096B1 (de)	1984-11-07	N-Aminomethyl-halogenacetanilide, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
DE1912294C (de)	1973-03-22	Oximcarbamate und ihre Verwendung als Akaricide
DE3431856A1 (de)	1986-03-06	Fungizide mittel auf acylanilin-derivat-basis
DE2901626A1 (de)	1980-07-31	N-sulfenylierte diurethane