CA1048518A - Herbicidal anilides, herbicidal-n-(acyl-tertiary-amidoalkyl) anilides, and herbicidal acyloxyalkyl anilides - Google Patents
Herbicidal anilides, herbicidal-n-(acyl-tertiary-amidoalkyl) anilides, and herbicidal acyloxyalkyl anilidesInfo
- Publication number
- CA1048518A CA1048518A CA72143810A CA143810A CA1048518A CA 1048518 A CA1048518 A CA 1048518A CA 72143810 A CA72143810 A CA 72143810A CA 143810 A CA143810 A CA 143810A CA 1048518 A CA1048518 A CA 1048518A
- Authority
- CA
- Canada
- Prior art keywords
- chloro
- acetanilide
- diethyl
- alkyl
- carbon atoms
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- -1 acyloxyalkyl anilides Chemical class 0.000 title claims abstract description 129
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 18
- 150000003931 anilides Chemical class 0.000 title description 5
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 title 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000001301 oxygen Substances 0.000 claims abstract description 18
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 18
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
- 239000011593 sulfur Substances 0.000 claims abstract description 14
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 12
- 239000000460 chlorine Substances 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 11
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 8
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 125000005188 oxoalkyl group Chemical group 0.000 claims abstract description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims abstract description 4
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000005452 alkenyloxyalkyl group Chemical group 0.000 claims abstract description 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000005018 aryl alkenyl group Chemical group 0.000 claims abstract description 4
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims abstract description 4
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims abstract description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 4
- 125000003106 haloaryl group Chemical group 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000005358 mercaptoalkyl group Chemical group 0.000 claims abstract description 4
- 125000004999 nitroaryl group Chemical group 0.000 claims abstract description 4
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 3
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims description 71
- 229960001413 acetanilide Drugs 0.000 claims description 38
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 claims description 35
- 239000002689 soil Substances 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- HKWKQDFJSLCGJA-UHFFFAOYSA-N 2-chloro-N-(2,6-diethylphenyl)-N-[(2,5-dioxopyrrolidin-1-yl)methyl]acetamide Chemical compound ClCC(=O)N(C1=C(C=CC=C1CC)CC)CN1C(CCC1=O)=O HKWKQDFJSLCGJA-UHFFFAOYSA-N 0.000 claims description 3
- YFOKZOUYEKMQFO-UHFFFAOYSA-N N-(acetamidomethyl)-2-chloro-N-(2-ethyl-6-methylphenyl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(CNC(C)=O)C(=O)CCl YFOKZOUYEKMQFO-UHFFFAOYSA-N 0.000 claims description 3
- ICPUTBOCWXQLKO-UHFFFAOYSA-N (N-(2-chloroacetyl)-2,6-diethylanilino)methyl 2-methylprop-2-enoate Chemical compound ClCC(=O)N(C1=C(C=CC=C1CC)CC)COC(C(=C)C)=O ICPUTBOCWXQLKO-UHFFFAOYSA-N 0.000 claims description 2
- LAQMSWCWDAJJNX-UHFFFAOYSA-N 3-chloro-N-[(N-(2-chloroacetyl)-2,6-diethylanilino)methyl]propanamide Chemical compound CCC1=CC=CC(CC)=C1N(CNC(=O)CCCl)C(=O)CCl LAQMSWCWDAJJNX-UHFFFAOYSA-N 0.000 claims description 2
- XCLPNQDDJZWVKA-UHFFFAOYSA-N (N-(2-chloroacetyl)-2,6-diethylanilino)methyl propanoate Chemical compound CCC(=O)OCN(C(=O)CCl)C1=C(CC)C=CC=C1CC XCLPNQDDJZWVKA-UHFFFAOYSA-N 0.000 claims 2
- SNPZDXACCGIJNK-UHFFFAOYSA-N N-Acetyl-2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1NC(C)=O SNPZDXACCGIJNK-UHFFFAOYSA-N 0.000 claims 2
- QINWXQCOVCNIML-UHFFFAOYSA-N N-[(N-(2-chloroacetyl)-2,6-diethylanilino)methyl]cyclopropanecarboxamide Chemical compound ClCC(=O)N(C1=C(C=CC=C1CC)CC)CNC(=O)C1CC1 QINWXQCOVCNIML-UHFFFAOYSA-N 0.000 claims 2
- QTGVGIVRLSGTJJ-UHFFFAOYSA-N n-(acetamidomethyl)-2-chloro-n-(2,6-diethylphenyl)acetamide Chemical compound CCC1=CC=CC(CC)=C1N(CNC(C)=O)C(=O)CCl QTGVGIVRLSGTJJ-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 abstract description 42
- 239000011541 reaction mixture Substances 0.000 description 29
- 239000007787 solid Substances 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 241000196324 Embryophyta Species 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- ZROZUVJQGAITPU-UHFFFAOYSA-N 2-chloro-n-(2,6-diethylphenyl)-n-(hydroxymethyl)acetamide Chemical compound CCC1=CC=CC(CC)=C1N(CO)C(=O)CCl ZROZUVJQGAITPU-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 9
- 239000004606 Fillers/Extenders Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 229940076134 benzene Drugs 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- PDQMMZXYWKOZHY-UHFFFAOYSA-N 2-chloro-n-(chloromethyl)-n-(2,6-diethylphenyl)acetamide Chemical compound CCC1=CC=CC(CC)=C1N(CCl)C(=O)CCl PDQMMZXYWKOZHY-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 239000002270 dispersing agent Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 229960003390 magnesium sulfate Drugs 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 6
- 150000002825 nitriles Chemical class 0.000 description 6
- 229940032330 sulfuric acid Drugs 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000002671 adjuvant Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 235000001508 sulfur Nutrition 0.000 description 5
- 229960005349 sulfur Drugs 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 239000012223 aqueous fraction Substances 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 239000004009 herbicide Substances 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- OVSKIKFHRZPJSS-UHFFFAOYSA-M (2,4-dichlorophenoxy)acetate Chemical compound [O-]C(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-M 0.000 description 3
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 3
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- QKIJBCHXAIIORE-UHFFFAOYSA-N N-[(2,6-diethylanilino)methyl]-N-methylacetamide Chemical compound CN(C(C)=O)CNC1=C(C=CC=C1CC)CC QKIJBCHXAIIORE-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000008061 acetanilides Chemical class 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 229960000892 attapulgite Drugs 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- ZMBSRNHDTFKMLI-UHFFFAOYSA-N n-(2,6-diethylphenyl)methanimine Chemical compound CCC1=CC=CC(CC)=C1N=C ZMBSRNHDTFKMLI-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052625 palygorskite Inorganic materials 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- AILFUJLJBZHALD-UHFFFAOYSA-N (2-tert-butyl-N-(2-chloroacetyl)-6-methylanilino)methyl 2-methylprop-2-enoate Chemical compound ClCC(=O)N(C1=C(C=CC=C1C(C)(C)C)C)COC(C(=C)C)=O AILFUJLJBZHALD-UHFFFAOYSA-N 0.000 description 2
- KSKXSXDBCMZOIZ-UHFFFAOYSA-N (6-tert-butyl-N-(2-chloroacetyl)-2,3-dimethylanilino)methyl acetate Chemical compound ClCC(=O)N(C1=C(C(=CC=C1C(C)(C)C)C)C)COC(C)=O KSKXSXDBCMZOIZ-UHFFFAOYSA-N 0.000 description 2
- NENHNCTXNINYQQ-UHFFFAOYSA-N (N-(2-chloroacetyl)-2,6-diethylanilino)methyl 2-phenylacetate Chemical compound ClCC(=O)N(C1=C(C=CC=C1CC)CC)COC(CC1=CC=CC=C1)=O NENHNCTXNINYQQ-UHFFFAOYSA-N 0.000 description 2
- IWFQWKJZSTYXOE-UHFFFAOYSA-N (N-(2-chloroacetyl)-2,6-diethylanilino)methyl octanoate Chemical compound ClCC(=O)N(C1=C(C=CC=C1CC)CC)COC(CCCCCCC)=O IWFQWKJZSTYXOE-UHFFFAOYSA-N 0.000 description 2
- YYIUHTJBWLOOCU-UHFFFAOYSA-N 2-(N-(2-chloroacetyl)-2-ethyl-6-methylanilino)ethyl cyclopropanecarboxylate Chemical compound CCC1=C(N(CCOC(=O)C2CC2)C(=O)CCl)C(C)=CC=C1 YYIUHTJBWLOOCU-UHFFFAOYSA-N 0.000 description 2
- ZYJCANOFPJNOCC-UHFFFAOYSA-N 2-[N-(2-chloroacetyl)-2,6-di(propan-2-yl)anilino]ethyl butanoate Chemical compound ClCC(=O)N(C1=C(C=CC=C1C(C)C)C(C)C)CCOC(CCC)=O ZYJCANOFPJNOCC-UHFFFAOYSA-N 0.000 description 2
- AJZCUGWIYAAFKM-UHFFFAOYSA-N 2-bromo-N-(2,6-diethylphenyl)-N-[(2,5-dioxopyrrol-1-yl)methyl]acetamide Chemical compound BrCC(=O)N(C1=C(C=CC=C1CC)CC)CN1C(C=CC1=O)=O AJZCUGWIYAAFKM-UHFFFAOYSA-N 0.000 description 2
- HUECKTSAZLBQNG-UHFFFAOYSA-N 2-bromo-N-(2-ethyl-6-methylphenyl)-N-[2-(3-methyl-2,5-dioxopyrrol-1-yl)ethyl]acetamide Chemical compound BrCC(=O)N(C1=C(C=CC=C1C)CC)CCN1C(C(C)=CC1=O)=O HUECKTSAZLBQNG-UHFFFAOYSA-N 0.000 description 2
- PODFOJCRDDHKND-UHFFFAOYSA-N 2-bromo-N-[2-(2,5-dioxopyrrol-1-yl)ethyl]-N-(2-ethyl-6-methylphenyl)acetamide Chemical compound BrCC(=O)N(C1=C(C=CC=C1C)CC)CCN1C(C=CC1=O)=O PODFOJCRDDHKND-UHFFFAOYSA-N 0.000 description 2
- GICVMUKMDIFZRF-UHFFFAOYSA-N 2-bromo-N-[2-(2,5-dioxopyrrolidin-1-yl)ethyl]-N-(2-ethyl-6-methylphenyl)acetamide Chemical compound BrCC(=O)N(C1=C(C=CC=C1C)CC)CCN1C(CCC1=O)=O GICVMUKMDIFZRF-UHFFFAOYSA-N 0.000 description 2
- QQOAGRBTACNBBZ-UHFFFAOYSA-N 2-chloro-N-(2,6-diethylphenyl)-N-(2-formamidoethyl)acetamide Chemical compound ClCC(=O)N(C1=C(C=CC=C1CC)CC)CCNC=O QQOAGRBTACNBBZ-UHFFFAOYSA-N 0.000 description 2
- NUHHIMRLJKYSBR-UHFFFAOYSA-N 2-chloro-N-(2,6-diethylphenyl)-N-[(2,5-dioxopyrrol-1-yl)methyl]acetamide Chemical compound ClCC(=O)N(C1=C(C=CC=C1CC)CC)CN1C(C=CC1=O)=O NUHHIMRLJKYSBR-UHFFFAOYSA-N 0.000 description 2
- DHERMRZVKLODCV-UHFFFAOYSA-N 2-chloro-N-(2,6-diethylphenyl)-N-[(3-methyl-2,5-dioxopyrrol-1-yl)methyl]acetamide Chemical compound ClCC(=O)N(C1=C(C=CC=C1CC)CC)CN1C(C(C)=CC1=O)=O DHERMRZVKLODCV-UHFFFAOYSA-N 0.000 description 2
- MBFBDWCMKITVPJ-UHFFFAOYSA-N 2-chloro-N-(2,6-diethylphenyl)-N-[(pentanethioylamino)methyl]acetamide Chemical compound ClCC(=O)N(C1=C(C=CC=C1CC)CC)CNC(CCCC)=S MBFBDWCMKITVPJ-UHFFFAOYSA-N 0.000 description 2
- XBQSXDYGKDIMBY-UHFFFAOYSA-N 2-chloro-N-(2,6-dimethylphenyl)-N-[(2,5-dioxopyrrolidin-1-yl)methyl]acetamide Chemical compound ClCC(=O)N(C1=C(C=CC=C1C)C)CN1C(CCC1=O)=O XBQSXDYGKDIMBY-UHFFFAOYSA-N 0.000 description 2
- QXGSYGRUPNKPKH-UHFFFAOYSA-N 2-chloro-N-(2,6-dimethylphenyl)-N-[(3-methyl-2,5-dioxopyrrol-1-yl)methyl]acetamide Chemical compound ClCC(=O)N(C1=C(C=CC=C1C)C)CN1C(C(C)=CC1=O)=O QXGSYGRUPNKPKH-UHFFFAOYSA-N 0.000 description 2
- LPGUZWADTFVSBO-UHFFFAOYSA-N 2-chloro-N-(2,6-dimethylphenyl)-N-[2-(2,5-dioxopyrrol-1-yl)ethyl]acetamide Chemical compound ClCC(=O)N(C1=C(C=CC=C1C)C)CCN1C(C=CC1=O)=O LPGUZWADTFVSBO-UHFFFAOYSA-N 0.000 description 2
- CEOLIJUCKMBWEH-UHFFFAOYSA-N 2-chloro-N-(2,6-dimethylphenyl)-N-[2-(3-methyl-2,5-dioxopyrrol-1-yl)ethyl]acetamide Chemical compound ClCC(=O)N(C1=C(C=CC=C1C)C)CCN1C(C(C)=CC1=O)=O CEOLIJUCKMBWEH-UHFFFAOYSA-N 0.000 description 2
- UNANLQZSGWAGQU-UHFFFAOYSA-N 3-chloro-N-[2-(N-(2-chloroacetyl)-2,6-diethylanilino)ethyl]-2-methylpropanamide Chemical compound ClCC(=O)N(C1=C(C=CC=C1CC)CC)CCNC(C(CCl)C)=O UNANLQZSGWAGQU-UHFFFAOYSA-N 0.000 description 2
- PPDRLQLKHRZIJC-UHFFFAOYSA-N 5-nitrosalicylic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1O PPDRLQLKHRZIJC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 240000006122 Chenopodium album Species 0.000 description 2
- 235000009344 Chenopodium album Nutrition 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 2
- 240000003176 Digitaria ciliaris Species 0.000 description 2
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 2
- 235000005476 Digitaria cruciata Nutrition 0.000 description 2
- 235000006830 Digitaria didactyla Nutrition 0.000 description 2
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
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- PSFYDISNNZLGCM-UHFFFAOYSA-N n-[(n-(2-chloroacetyl)-2-ethyl-6-methylanilino)methyl]cyclopropanecarboxamide Chemical compound CCC1=CC=CC(C)=C1N(C(=O)CCl)CNC(=O)C1CC1 PSFYDISNNZLGCM-UHFFFAOYSA-N 0.000 description 1
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- XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 1
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- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
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- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000005359 phenoxyalkyl group Chemical group 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 208000037974 severe injury Diseases 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229940045998 sodium isethionate Drugs 0.000 description 1
- LADXKQRVAFSPTR-UHFFFAOYSA-M sodium;2-hydroxyethanesulfonate Chemical compound [Na+].OCCS([O-])(=O)=O LADXKQRVAFSPTR-UHFFFAOYSA-M 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
- C07C275/14—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
- C07D207/408—Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
- C07D207/452—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US14889271A | 1971-06-01 | 1971-06-01 | |
US00148894A US3830829A (en) | 1971-06-01 | 1971-06-01 | Chlorophenoxyalkyl anilides |
US00148893A US3830841A (en) | 1971-06-01 | 1971-06-01 | Herbicidal anilides |
Publications (1)
Publication Number | Publication Date |
---|---|
CA1048518A true CA1048518A (en) | 1979-02-13 |
Family
ID=27386757
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA72143810A Expired CA1048518A (en) | 1971-06-01 | 1972-05-31 | Herbicidal anilides, herbicidal-n-(acyl-tertiary-amidoalkyl) anilides, and herbicidal acyloxyalkyl anilides |
Country Status (17)
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2744396A1 (de) * | 1977-10-03 | 1979-04-12 | Basf Ag | Acetanilide |
DE3130302A1 (de) * | 1981-07-31 | 1983-02-17 | Basf Ag, 6700 Ludwigshafen | N-carbamoylmethyl-haogenacetanilide, verfahren zu ihrer herstellung und diese enthaltende herbizide |
EP0194985A3 (en) * | 1985-02-13 | 1987-09-23 | Monsanto Company | Method for the regulation of the natural growth of turf grass |
EP0192628A1 (en) * | 1985-02-13 | 1986-08-27 | Monsanto Company | Novel acetanilides and their use in the regulation of the natural growth or development of turf grass |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR6677387D0 (pt) * | 1965-10-14 | 1973-12-26 | Monsanto Co | Composicao fitotoxica bem como processo para a preparacao de alfa-haloacetaniladas usadas como ingredientes ativos na dita composicao |
-
1972
- 1972-05-29 NL NL727207261A patent/NL150775B/xx not_active IP Right Cessation
- 1972-05-29 IL IL39562A patent/IL39562A/en unknown
- 1972-05-31 DD DD163323A patent/DD104174A5/xx unknown
- 1972-05-31 DE DE2226593A patent/DE2226593C3/de not_active Expired
- 1972-05-31 FR FR7219542A patent/FR2140134B1/fr not_active Expired
- 1972-05-31 BE BE784212A patent/BE784212A/xx not_active IP Right Cessation
- 1972-05-31 CA CA72143810A patent/CA1048518A/en not_active Expired
- 1972-05-31 GB GB2536372A patent/GB1380436A/en not_active Expired
- 1972-05-31 BR BR3495/72A patent/BR7203495D0/pt unknown
- 1972-05-31 IT IT25147/72A patent/IT956065B/it active
- 1972-05-31 CH CH801772A patent/CH580909A5/xx not_active IP Right Cessation
- 1972-05-31 SU SU721793620A patent/SU605519A3/ru active
- 1972-05-31 BG BG020618A patent/BG26654A3/xx unknown
- 1972-05-31 CS CS723753A patent/CS191164B2/cs unknown
- 1972-05-31 JP JP5349972A patent/JPS5542961B1/ja active Pending
- 1972-05-31 PL PL1972155706A patent/PL84702B1/pl unknown
- 1972-05-31 HU HUMO836A patent/HU166275B/hu unknown
Also Published As
Publication number | Publication date |
---|---|
BG26654A3 (bg) | 1979-05-15 |
HU166275B (enrdf_load_stackoverflow) | 1975-02-28 |
DE2226593B2 (de) | 1977-09-01 |
DD104174A5 (enrdf_load_stackoverflow) | 1974-03-05 |
DE2226593C3 (de) | 1978-04-27 |
JPS5542961B1 (enrdf_load_stackoverflow) | 1980-11-04 |
GB1380436A (en) | 1975-01-15 |
FR2140134A1 (enrdf_load_stackoverflow) | 1973-01-12 |
IL39562A (en) | 1977-10-31 |
IL39562A0 (en) | 1972-07-26 |
CH580909A5 (enrdf_load_stackoverflow) | 1976-10-29 |
DE2226593A1 (de) | 1972-12-14 |
NL7207261A (enrdf_load_stackoverflow) | 1972-12-05 |
SU605519A3 (ru) | 1978-04-30 |
NL150775B (nl) | 1976-09-15 |
BE784212A (fr) | 1972-11-30 |
IT956065B (it) | 1973-10-10 |
FR2140134B1 (enrdf_load_stackoverflow) | 1979-09-07 |
BR7203495D0 (pt) | 1973-09-18 |
PL84702B1 (en) | 1976-04-30 |
CS191164B2 (en) | 1979-06-29 |
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