CA1100998A - 2,6-dinitroaniline herbicides - Google Patents
2,6-dinitroaniline herbicidesInfo
- Publication number
- CA1100998A CA1100998A CA267,749A CA267749A CA1100998A CA 1100998 A CA1100998 A CA 1100998A CA 267749 A CA267749 A CA 267749A CA 1100998 A CA1100998 A CA 1100998A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- sec
- formula
- dinitroaniline
- methoxymethyl
- 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
- QFUSCYRJMXLNRB-UHFFFAOYSA-N 2,6-dinitroaniline Chemical compound NC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O QFUSCYRJMXLNRB-UHFFFAOYSA-N 0.000 title abstract description 5
- 239000004009 herbicide Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 15
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 11
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- RFONJRMUUALMBA-UHFFFAOYSA-N 2-methanidylpropane Chemical group CC(C)[CH2-] RFONJRMUUALMBA-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract 2
- -1 N-isopropyl-4-isopropyl-3-(methoxymethyl)-2,6-dinitroaniline Chemical compound 0.000 claims description 23
- 241000196324 Embryophyta Species 0.000 claims description 20
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000002689 soil Substances 0.000 claims description 7
- 239000002808 molecular sieve Substances 0.000 claims description 6
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 claims description 4
- 150000001448 anilines Chemical class 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000005932 reductive alkylation reaction Methods 0.000 claims description 3
- 230000000802 nitrating effect Effects 0.000 claims description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- RJPWHQIQFHLWLS-UHFFFAOYSA-N 3-(methoxymethyl)-4-methyl-2,6-dinitro-n-pentan-3-ylaniline Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(COC)=C1[N+]([O-])=O RJPWHQIQFHLWLS-UHFFFAOYSA-N 0.000 claims 3
- QFMUZADDTARVMO-UHFFFAOYSA-N 3-methyl-2,6-dinitro-n-propan-2-yl-4-propylaniline Chemical compound CCCC1=CC([N+]([O-])=O)=C(NC(C)C)C([N+]([O-])=O)=C1C QFMUZADDTARVMO-UHFFFAOYSA-N 0.000 claims 1
- LPSBAKFXSFLYHG-UHFFFAOYSA-N 4-butan-2-yl-3-(methoxymethyl)-2,6-dinitro-n-pentan-3-ylaniline Chemical compound CCC(C)C1=CC([N+]([O-])=O)=C(NC(CC)CC)C([N+]([O-])=O)=C1COC LPSBAKFXSFLYHG-UHFFFAOYSA-N 0.000 claims 1
- XHERWHUFDAWNQV-UHFFFAOYSA-N 4-ethyl-3-(methoxymethyl)-2,6-dinitro-n-pentan-2-ylaniline Chemical compound CCCC(C)NC1=C([N+]([O-])=O)C=C(CC)C(COC)=C1[N+]([O-])=O XHERWHUFDAWNQV-UHFFFAOYSA-N 0.000 claims 1
- HHDCPKJKOXEMQQ-UHFFFAOYSA-N 4-ethyl-3-(methoxymethyl)-2,6-dinitro-n-pentan-3-ylaniline Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(CC)C(COC)=C1[N+]([O-])=O HHDCPKJKOXEMQQ-UHFFFAOYSA-N 0.000 claims 1
- WPFCZGPGSDWBMF-UHFFFAOYSA-N 4-ethyl-3-(methoxymethyl)-2,6-dinitro-n-propan-2-ylaniline Chemical compound CCC1=CC([N+]([O-])=O)=C(NC(C)C)C([N+]([O-])=O)=C1COC WPFCZGPGSDWBMF-UHFFFAOYSA-N 0.000 claims 1
- NBWKAEULHDXDKX-UHFFFAOYSA-N 4-ethyl-3-methyl-2,6-dinitro-n-pentan-3-ylaniline Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(CC)C(C)=C1[N+]([O-])=O NBWKAEULHDXDKX-UHFFFAOYSA-N 0.000 claims 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 claims 1
- 125000005233 alkylalcohol group Chemical group 0.000 claims 1
- 125000001118 alkylidene group Chemical group 0.000 claims 1
- FEVASFPJNVOTJB-UHFFFAOYSA-N n-butan-2-yl-4-ethyl-3-(methoxymethyl)-2,6-dinitroaniline Chemical compound CCC(C)NC1=C([N+]([O-])=O)C=C(CC)C(COC)=C1[N+]([O-])=O FEVASFPJNVOTJB-UHFFFAOYSA-N 0.000 claims 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 71
- 230000002363 herbicidal effect Effects 0.000 abstract description 20
- 239000000243 solution Substances 0.000 description 53
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 239000010502 orange oil Substances 0.000 description 31
- 235000019502 Orange oil Nutrition 0.000 description 28
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 24
- 239000003921 oil Substances 0.000 description 24
- 235000019198 oils Nutrition 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000012043 crude product Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 229960003390 magnesium sulfate Drugs 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- KUGRPPRAQNPSQD-UHFFFAOYSA-N OOOOO Chemical compound OOOOO KUGRPPRAQNPSQD-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 229940073584 methylene chloride Drugs 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 229960001701 chloroform Drugs 0.000 description 7
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 229910017604 nitric acid Inorganic materials 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- 244000036975 Ambrosia artemisiifolia Species 0.000 description 5
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 5
- 240000006410 Sida spinosa Species 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 244000237956 Amaranthus retroflexus Species 0.000 description 4
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 4
- 244000152970 Digitaria sanguinalis Species 0.000 description 4
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 4
- 244000058871 Echinochloa crus-galli Species 0.000 description 4
- 244000275012 Sesbania cannabina Species 0.000 description 4
- 240000003461 Setaria viridis Species 0.000 description 4
- 235000002248 Setaria viridis Nutrition 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-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
- 239000004480 active ingredient Substances 0.000 description 4
- 239000011149 active material Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 230000036244 malformation Effects 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- 240000006995 Abutilon theophrasti Species 0.000 description 3
- 235000003129 Ambrosia artemisiifolia var elatior Nutrition 0.000 description 3
- 235000003351 Brassica cretica Nutrition 0.000 description 3
- 244000056139 Brassica cretica Species 0.000 description 3
- 235000003343 Brassica rupestris Nutrition 0.000 description 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 3
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 3
- 235000005476 Digitaria cruciata Nutrition 0.000 description 3
- 235000006830 Digitaria didactyla Nutrition 0.000 description 3
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 3
- 235000014716 Eleusine indica Nutrition 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 244000299507 Gossypium hirsutum Species 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- RTYZCUMXOXNVSI-UHFFFAOYSA-N OOOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOOO RTYZCUMXOXNVSI-UHFFFAOYSA-N 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000002834 Sida rhombifolia Nutrition 0.000 description 3
- 241000209149 Zea Species 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 235000003484 annual ragweed Nutrition 0.000 description 3
- 235000006263 bur ragweed Nutrition 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 235000003488 common ragweed Nutrition 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- 239000000428 dust Substances 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 235000010460 mustard Nutrition 0.000 description 3
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 235000009736 ragweed Nutrition 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 229960001407 sodium bicarbonate Drugs 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- CUZLJOLBIRPEFB-UHFFFAOYSA-N 1-methoxypropan-2-one Chemical compound COCC(C)=O CUZLJOLBIRPEFB-UHFFFAOYSA-N 0.000 description 2
- YXWWHNCQZBVZPV-UHFFFAOYSA-N 2'-methylacetophenone Chemical compound CC(=O)C1=CC=CC=C1C YXWWHNCQZBVZPV-UHFFFAOYSA-N 0.000 description 2
- GTZCGGUHTKVHSB-UHFFFAOYSA-N 2-(methoxymethyl)-1-methyl-4-nitrobenzene Chemical compound COCC1=CC([N+]([O-])=O)=CC=C1C GTZCGGUHTKVHSB-UHFFFAOYSA-N 0.000 description 2
- DOLQYFPDPKPQSS-UHFFFAOYSA-N 3,4-dimethylaniline Chemical group CC1=CC=C(N)C=C1C DOLQYFPDPKPQSS-UHFFFAOYSA-N 0.000 description 2
- XISGUUHMKBGXHJ-UHFFFAOYSA-N 4-chloro-1-methyl-3,5-dinitro-2-propan-2-ylbenzene Chemical compound CC(C)C1=C(C)C=C([N+]([O-])=O)C(Cl)=C1[N+]([O-])=O XISGUUHMKBGXHJ-UHFFFAOYSA-N 0.000 description 2
- AYYXALUTEYXFHA-UHFFFAOYSA-N 4-methyl-2,6-dinitro-3-propan-2-yl-n,n-dipropylaniline Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C)C(C(C)C)=C1[N+]([O-])=O AYYXALUTEYXFHA-UHFFFAOYSA-N 0.000 description 2
- SHCLWCGJHOMCRX-UHFFFAOYSA-N 4-methyl-3-propan-2-ylaniline Chemical compound CC(C)C1=CC(N)=CC=C1C SHCLWCGJHOMCRX-UHFFFAOYSA-N 0.000 description 2
- VNSDYWDUIDZMQW-UHFFFAOYSA-N 4-methyl-n-pentan-3-yl-3-propan-2-ylaniline Chemical compound CCC(CC)NC1=CC=C(C)C(C(C)C)=C1 VNSDYWDUIDZMQW-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 235000004135 Amaranthus viridis Nutrition 0.000 description 2
- 235000003133 Ambrosia artemisiifolia Nutrition 0.000 description 2
- 235000009344 Chenopodium album Nutrition 0.000 description 2
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 2
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- 229920000742 Cotton Polymers 0.000 description 2
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- 241000207783 Ipomoea Species 0.000 description 2
- 235000003403 Limnocharis flava Nutrition 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- DTAFLBZLAZYRDX-UHFFFAOYSA-N OOOOOO Chemical compound OOOOOO DTAFLBZLAZYRDX-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 235000010086 Setaria viridis var. viridis Nutrition 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
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- 239000008187 granular material Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 208000006278 hypochromic anemia Diseases 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 239000000543 intermediate Substances 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
- 229940057952 methanol Drugs 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical class [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- GOECEMHOAOBUEA-UHFFFAOYSA-N 1-(2-methyl-5-nitrophenyl)ethanone Chemical compound CC(=O)C1=CC([N+]([O-])=O)=CC=C1C GOECEMHOAOBUEA-UHFFFAOYSA-N 0.000 description 1
- WSRZKLUAFXDQLG-UHFFFAOYSA-N 1-ethyl-2-(methoxymethyl)-4-nitrobenzene Chemical compound CCC1=CC=C([N+]([O-])=O)C=C1COC WSRZKLUAFXDQLG-UHFFFAOYSA-N 0.000 description 1
- RESTWAHJFMZUIZ-UHFFFAOYSA-N 1-ethyl-4-nitrobenzene Chemical compound CCC1=CC=C([N+]([O-])=O)C=C1 RESTWAHJFMZUIZ-UHFFFAOYSA-N 0.000 description 1
- HBCZMIJXNQCIDC-UHFFFAOYSA-N 2-(chloromethyl)-1-methyl-4-nitrobenzene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1CCl HBCZMIJXNQCIDC-UHFFFAOYSA-N 0.000 description 1
- BCSRQPDGMAVORY-UHFFFAOYSA-N 2-(chloromethyl)-4-nitro-1-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C([N+]([O-])=O)C=C1CCl BCSRQPDGMAVORY-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- VWORTXKJZJUAAR-UHFFFAOYSA-N 2-methyl-n-pentan-3-yl-5-propan-2-ylaniline Chemical compound CCC(CC)NC1=CC(C(C)C)=CC=C1C VWORTXKJZJUAAR-UHFFFAOYSA-N 0.000 description 1
- JTWHVBNYYWFXSI-UHFFFAOYSA-N 2-nitro-1-phenylethanone Chemical compound [O-][N+](=O)CC(=O)C1=CC=CC=C1 JTWHVBNYYWFXSI-UHFFFAOYSA-N 0.000 description 1
- VDFWYAJGVLMWNF-UHFFFAOYSA-N 3-(methoxymethyl)-4-methylaniline Chemical compound COCC1=CC(N)=CC=C1C VDFWYAJGVLMWNF-UHFFFAOYSA-N 0.000 description 1
- CSHZBXAFUZOGGS-UHFFFAOYSA-N 4-chloro-1-ethyl-2-(methoxymethyl)-3,5-dinitrobenzene Chemical compound CCC1=CC([N+]([O-])=O)=C(Cl)C([N+]([O-])=O)=C1COC CSHZBXAFUZOGGS-UHFFFAOYSA-N 0.000 description 1
- LLVMUANLCPNAAV-UHFFFAOYSA-N 4-methyl-3-propan-2-ylaniline;hydrochloride Chemical compound Cl.CC(C)C1=CC(N)=CC=C1C LLVMUANLCPNAAV-UHFFFAOYSA-N 0.000 description 1
- 241000219144 Abutilon Species 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- COYKKJDJKCZITC-UHFFFAOYSA-N C[O-].[Na+].COCC1=C(C=CC(=C1)[N+](=O)[O-])CC Chemical compound C[O-].[Na+].COCC1=C(C=CC(=C1)[N+](=O)[O-])CC COYKKJDJKCZITC-UHFFFAOYSA-N 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- FVIGODVHAVLZOO-UHFFFAOYSA-N Dixanthogen Chemical compound CCOC(=S)SSC(=S)OCC FVIGODVHAVLZOO-UHFFFAOYSA-N 0.000 description 1
- 235000009432 Gossypium hirsutum Nutrition 0.000 description 1
- 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
- 240000001549 Ipomoea eriocarpa Species 0.000 description 1
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CQGRLHBOVUGVEA-UHFFFAOYSA-N OOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOO CQGRLHBOVUGVEA-UHFFFAOYSA-N 0.000 description 1
- HFEFMUSTGZNOPY-UHFFFAOYSA-N OOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOO HFEFMUSTGZNOPY-UHFFFAOYSA-N 0.000 description 1
- ZQTQPYJGMWHXMO-UHFFFAOYSA-N OOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOO ZQTQPYJGMWHXMO-UHFFFAOYSA-N 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 241000533293 Sesbania emerus Species 0.000 description 1
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XNFVGEUMTFIVHQ-UHFFFAOYSA-N disodium;sulfide;hydrate Chemical compound O.[Na+].[Na+].[S-2] XNFVGEUMTFIVHQ-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910000286 fullers earth Inorganic materials 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 210000001699 lower leg Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- GQKZBCPTCWJTAS-UHFFFAOYSA-N methoxymethylbenzene Chemical compound COCC1=CC=CC=C1 GQKZBCPTCWJTAS-UHFFFAOYSA-N 0.000 description 1
- KZDXSQUQFVFDTI-UHFFFAOYSA-N n-(methoxymethyl)-4-methylaniline Chemical compound COCNC1=CC=C(C)C=C1 KZDXSQUQFVFDTI-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/19—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups bound to carbon atoms of six-membered aromatic rings and hydroxy groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
- C07C205/12—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64322675A | 1975-12-22 | 1975-12-22 | |
| US643,226 | 1975-12-22 | ||
| US69608576A | 1976-06-14 | 1976-06-14 | |
| US696,085 | 1976-06-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1100998A true CA1100998A (en) | 1981-05-12 |
Family
ID=27094213
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA267,749A Expired CA1100998A (en) | 1975-12-22 | 1976-12-13 | 2,6-dinitroaniline herbicides |
Country Status (21)
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE787939A (fr) * | 1971-08-25 | 1973-02-26 | American Cyanamid Co | 2,6-dinitranilines possedant des proprietes herbicides |
-
1976
- 1976-12-08 IN IN2170/CAL/76A patent/IN145613B/en unknown
- 1976-12-10 IL IL51079A patent/IL51079A/xx unknown
- 1976-12-13 CA CA267,749A patent/CA1100998A/en not_active Expired
- 1976-12-15 GB GB52441/76A patent/GB1573014A/en not_active Expired
- 1976-12-17 DE DE19762657327 patent/DE2657327A1/de not_active Withdrawn
- 1976-12-21 IT IT52719/76A patent/IT1066705B/it active
- 1976-12-21 IE IE2801/76A patent/IE44488B1/en unknown
- 1976-12-21 SE SE7614384A patent/SE442109B/xx unknown
- 1976-12-21 DK DK574676A patent/DK574676A/da not_active Application Discontinuation
- 1976-12-21 CH CH1610676A patent/CH618076A5/de not_active IP Right Cessation
- 1976-12-21 BE BE173489A patent/BE849681R/xx active
- 1976-12-21 PT PT66000A patent/PT66000B/pt unknown
- 1976-12-21 OA OA56021A patent/OA05519A/xx unknown
- 1976-12-21 AT AT949076A patent/AT362612B/de not_active IP Right Cessation
- 1976-12-22 BG BG037521A patent/BG28256A4/xx unknown
- 1976-12-22 DD DD76203903A patent/DD134516A5/xx unknown
- 1976-12-22 DD DD7600196549A patent/DD130033A6/xx unknown
- 1976-12-22 AU AU20840/76A patent/AU514612B2/en not_active Ceased
- 1976-12-22 DD DD76203902A patent/DD134836A5/xx unknown
- 1976-12-22 JP JP51154802A patent/JPS5278841A/ja active Granted
- 1976-12-22 FI FI763684A patent/FI67209C/fi not_active IP Right Cessation
- 1976-12-22 BG BG034978A patent/BG27524A3/xx unknown
-
1980
- 1980-12-24 AU AU65872/80A patent/AU531431B2/en not_active Ceased
-
1981
- 1981-06-05 KE KE3135A patent/KE3135A/xx unknown
-
1982
- 1982-12-30 MY MY76/82A patent/MY8200076A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE849681R (fr) | 1977-06-21 |
| BG28256A4 (bg) | 1980-03-25 |
| JPS615469B2 (enrdf_load_stackoverflow) | 1986-02-18 |
| PT66000A (en) | 1977-01-01 |
| DD130033A6 (de) | 1978-03-01 |
| IN145613B (enrdf_load_stackoverflow) | 1978-11-18 |
| IT1066705B (it) | 1985-03-12 |
| DD134836A5 (de) | 1979-03-28 |
| FI67209B (fi) | 1984-10-31 |
| ATA949076A (de) | 1980-10-15 |
| AT362612B (de) | 1981-06-10 |
| IL51079A0 (en) | 1977-02-28 |
| FI763684A7 (enrdf_load_stackoverflow) | 1977-06-23 |
| OA05519A (fr) | 1981-04-30 |
| DE2657327A1 (de) | 1977-07-07 |
| PT66000B (en) | 1978-06-16 |
| FI67209C (fi) | 1985-02-11 |
| SE7614384L (sv) | 1977-06-23 |
| IE44488B1 (en) | 1981-12-16 |
| JPS5278841A (en) | 1977-07-02 |
| IL51079A (en) | 1981-11-30 |
| AU514612B2 (en) | 1981-02-19 |
| DD134516A5 (de) | 1979-03-07 |
| CH618076A5 (enrdf_load_stackoverflow) | 1980-07-15 |
| SE442109B (sv) | 1985-12-02 |
| DK574676A (da) | 1977-06-23 |
| IE44488L (en) | 1977-06-22 |
| KE3135A (en) | 1981-07-03 |
| GB1573014A (en) | 1980-08-13 |
| AU2084076A (en) | 1978-06-29 |
| MY8200076A (en) | 1982-12-31 |
| BG27524A3 (bg) | 1979-11-12 |
| AU531431B2 (en) | 1983-08-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |