CA1059140A - 2,6-dinitroanilines substituees en -3 - Google Patents

2,6-dinitroanilines substituees en -3

Info

Publication number: CA1059140A
Authority: CA; Canada
Prior art keywords: alkyl; alkenyl; chloro; compounds; hydrogen
Prior art date: 1975-06-23
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

Application number

CA254,945A

Other languages

English (en)

Inventor

James R. Beck

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Eli Lilly and Co

Original Assignee

Eli Lilly and Co

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.)

1975-06-23

Filing date

1976-06-16

Publication date

1979-07-24

1975-06-23 Priority claimed from US05/589,315 external-priority patent/US3987076A/en

1975-06-23 Priority claimed from US05/589,314 external-priority patent/US3948957A/en

1976-06-16 Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co

1979-07-24 Application granted granted Critical

1979-07-24 Publication of CA1059140A publication Critical patent/CA1059140A/fr

Status Expired legal-status Critical Current

Links

-1 3-(substituted)-2,6-dinitroanilines Chemical class 0.000 title claims abstract description 17
150000001875 compounds Chemical class 0.000 claims abstract description 45
239000004009 herbicide Substances 0.000 claims abstract description 9
125000000217 alkyl group Chemical group 0.000 claims description 38
125000003342 alkenyl group Chemical group 0.000 claims description 31
239000000203 mixture Substances 0.000 claims description 28
125000001309 chloro group Chemical group Cl* 0.000 claims description 27
239000001257 hydrogen Substances 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
239000007788 liquid Substances 0.000 claims description 10
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 8
239000000428 dust Substances 0.000 claims description 8
241000219095 Vitis Species 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 7
235000009754 Vitis X bourquina Nutrition 0.000 claims description 6
235000012333 Vitis X labruscana Nutrition 0.000 claims description 6
235000014787 Vitis vinifera Nutrition 0.000 claims description 6
241000233679 Peronosporaceae Species 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 5
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 5
239000012442 inert solvent Substances 0.000 claims description 5
239000007921 spray Substances 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 4
125000000068 chlorophenyl group Chemical group 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
229940080818 propionamide Drugs 0.000 claims description 4
230000000694 effects Effects 0.000 claims description 3
229910052979 sodium sulfide Inorganic materials 0.000 claims description 3
AXXSJVASKZIEJI-UHFFFAOYSA-N [2,4-dinitro-3-(pentan-3-ylamino)-6-(trifluoromethyl)phenyl] thiocyanate Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C(F)(F)F)C(SC#N)=C1[N+]([O-])=O AXXSJVASKZIEJI-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 9
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
YPUPPMAKJHKBPP-UHFFFAOYSA-N 3-azido-2,6-dinitro-n,n-dipropyl-4-(trifluoromethyl)aniline Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(N=[N+]=[N-])=C1[N+]([O-])=O YPUPPMAKJHKBPP-UHFFFAOYSA-N 0.000 claims 1
QDAMDNCSKRBYIZ-UHFFFAOYSA-N 3-azido-N-butyl-N-ethyl-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound CCCCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(N=[N+]=[N-])=C1[N+]([O-])=O QDAMDNCSKRBYIZ-UHFFFAOYSA-N 0.000 claims 1
229920000742 Cotton Polymers 0.000 claims 1
241000196324 Embryophyta Species 0.000 claims 1
244000068988 Glycine max Species 0.000 claims 1
235000010469 Glycine max Nutrition 0.000 claims 1
JXUGAKTVKCTBMA-UHFFFAOYSA-N [3-(dipropylamino)-2,4-dinitro-6-(trifluoromethyl)phenyl] thiocyanate Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(SC#N)=C1[N+]([O-])=O JXUGAKTVKCTBMA-UHFFFAOYSA-N 0.000 claims 1
UUXQFEIZKVXCMA-UHFFFAOYSA-N [3-[ethyl(2-methylprop-2-enyl)amino]-2,4-dinitro-6-(trifluoromethyl)phenyl] thiocyanate Chemical compound CC(=C)CN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(SC#N)=C1[N+]([O-])=O UUXQFEIZKVXCMA-UHFFFAOYSA-N 0.000 claims 1
125000003277 amino group Chemical group 0.000 claims 1
230000001419 dependent effect Effects 0.000 claims 1
239000002360 explosive Substances 0.000 claims 1
208000015181 infectious disease Diseases 0.000 claims 1
239000000543 intermediate Substances 0.000 claims 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims 1
239000000417 fungicide Substances 0.000 abstract description 3
239000003795 chemical substances by application Substances 0.000 abstract description 2
238000006073 displacement reaction Methods 0.000 abstract 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
239000003921 oil Substances 0.000 description 11
239000000047 product Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
150000002431 hydrogen Chemical class 0.000 description 9
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
239000002270 dispersing agent Substances 0.000 description 8
238000000921 elemental analysis Methods 0.000 description 8
239000005457 ice water Substances 0.000 description 8
230000002363 herbicidal effect Effects 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
239000007787 solid Substances 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 4
QFUSCYRJMXLNRB-UHFFFAOYSA-N 2,6-dinitroaniline Chemical class NC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O QFUSCYRJMXLNRB-UHFFFAOYSA-N 0.000 description 3
ZVKOAWGELPXYAQ-UHFFFAOYSA-N 3-chloro-2,6-dinitro-n-pentan-3-yl-4-(trifluoromethyl)aniline Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C(F)(F)F)C(Cl)=C1[N+]([O-])=O ZVKOAWGELPXYAQ-UHFFFAOYSA-N 0.000 description 3
FDSBMUJBQJNCNW-UHFFFAOYSA-N 3-chloro-2,6-dinitroaniline Chemical class NC1=C([N+]([O-])=O)C=CC(Cl)=C1[N+]([O-])=O FDSBMUJBQJNCNW-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 3
238000000034 method Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
DPQYRXNRGNLPFC-UHFFFAOYSA-N 2,4-dichloro-1,3-dinitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1Cl DPQYRXNRGNLPFC-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
239000000969 carrier Substances 0.000 description 2
230000000875 corresponding effect Effects 0.000 description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000010440 gypsum Substances 0.000 description 2
229910052602 gypsum Inorganic materials 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229910052903 pyrophyllite Inorganic materials 0.000 description 2
229940079101 sodium sulfide Drugs 0.000 description 2
ZGHLCBJZQLNUAZ-UHFFFAOYSA-N sodium sulfide nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[Na+].[S-2] ZGHLCBJZQLNUAZ-UHFFFAOYSA-N 0.000 description 2
229940048181 sodium sulfide nonahydrate Drugs 0.000 description 2
WMDLZMCDBSJMTM-UHFFFAOYSA-M sodium;sulfanide;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[SH-] WMDLZMCDBSJMTM-UHFFFAOYSA-M 0.000 description 2
238000010183 spectrum analysis Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
UZYRSBACWZIFIX-UHFFFAOYSA-N 1-(2,6-dinitrophenyl)piperidine Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1N1CCCCC1 UZYRSBACWZIFIX-UHFFFAOYSA-N 0.000 description 1
CGNBQYFXGQHUQP-UHFFFAOYSA-N 2,3-dinitroaniline Chemical class NC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O CGNBQYFXGQHUQP-UHFFFAOYSA-N 0.000 description 1
NPSUBWLTUMVJDW-UHFFFAOYSA-N 2-[3-(diethylamino)-2,4-dinitro-6-(trifluoromethyl)phenyl]sulfanylacetonitrile Chemical compound CCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(SCC#N)=C1[N+]([O-])=O NPSUBWLTUMVJDW-UHFFFAOYSA-N 0.000 description 1
XXINHFSTFOKVBJ-UHFFFAOYSA-N 2-[3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl]-1,1-dimethylhydrazine Chemical compound CN(C)NC1=C([N+]([O-])=O)C=C(C(F)(F)F)C(Cl)=C1[N+]([O-])=O XXINHFSTFOKVBJ-UHFFFAOYSA-N 0.000 description 1
VOZAGXXQTXAGLH-UHFFFAOYSA-N 3-[2,4-dinitro-3-(pentan-3-ylamino)-6-(trifluoromethyl)phenyl]sulfanylpropanenitrile Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C(F)(F)F)C(SCCC#N)=C1[N+]([O-])=O VOZAGXXQTXAGLH-UHFFFAOYSA-N 0.000 description 1
CXFIBJPFPNKLOK-UHFFFAOYSA-N 3-[3-(methylamino)-2,4-dinitro-6-(trifluoromethyl)phenyl]sulfanylpropanenitrile Chemical compound CNC1=C([N+]([O-])=O)C=C(C(F)(F)F)C(SCCC#N)=C1[N+]([O-])=O CXFIBJPFPNKLOK-UHFFFAOYSA-N 0.000 description 1
PIQAXMRNGRQDIR-UHFFFAOYSA-N 3-azido-2,6-dinitroaniline Chemical class NC1=C([N+]([O-])=O)C=CC(N=[N+]=[N-])=C1[N+]([O-])=O PIQAXMRNGRQDIR-UHFFFAOYSA-N 0.000 description 1
QJQTYPGNGXEDPO-UHFFFAOYSA-N 3-azido-n,n-dimethyl-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound CN(C)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(N=[N+]=[N-])=C1[N+]([O-])=O QJQTYPGNGXEDPO-UHFFFAOYSA-N 0.000 description 1
USJZRMMIXCKQRV-UHFFFAOYSA-N 3-chloro-n,n-diethyl-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound CCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(Cl)=C1[N+]([O-])=O USJZRMMIXCKQRV-UHFFFAOYSA-N 0.000 description 1
OTMGRWAAWZZGNV-UHFFFAOYSA-N 3-chloro-n,n-dimethyl-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound CN(C)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(Cl)=C1[N+]([O-])=O OTMGRWAAWZZGNV-UHFFFAOYSA-N 0.000 description 1
KQTFGEVSVQCIMP-UHFFFAOYSA-N 4-bromo-n,n-dimethyl-2,6-dinitroaniline Chemical compound CN(C)C1=C([N+]([O-])=O)C=C(Br)C=C1[N+]([O-])=O KQTFGEVSVQCIMP-UHFFFAOYSA-N 0.000 description 1
AJTATNCVSXZDBT-UHFFFAOYSA-N 4-iodo-n,n-dimethyl-2,6-dinitroaniline Chemical compound CN(C)C1=C([N+]([O-])=O)C=C(I)C=C1[N+]([O-])=O AJTATNCVSXZDBT-UHFFFAOYSA-N 0.000 description 1
UDVZOMAEGATTSE-UHFFFAOYSA-N 4-methyl-2,6-dinitro-n,n-dipropylaniline Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C)C=C1[N+]([O-])=O UDVZOMAEGATTSE-UHFFFAOYSA-N 0.000 description 1
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
241001281803 Plasmopara viticola Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 1
DWTLUOIUPZTFIG-UHFFFAOYSA-N n,n,4-trimethyl-2,6-dinitroaniline Chemical compound CN(C)C1=C([N+]([O-])=O)C=C(C)C=C1[N+]([O-])=O DWTLUOIUPZTFIG-UHFFFAOYSA-N 0.000 description 1
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 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000003209 petroleum derivative Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229960001866 silicon dioxide Drugs 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CA254,945A 1975-06-23 1976-06-16 2,6-dinitroanilines substituees en -3 Expired CA1059140A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US05/589,315 US3987076A (en)	1975-06-23	1975-06-23	2,6-dinitro-3-thiocyanatoanilines
US05/589,314 US3948957A (en)	1975-06-23	1975-06-23	3-Azido-2,6-dinitroanilines

Publications (1)

Publication Number	Publication Date
CA1059140A true CA1059140A (fr)	1979-07-24

Family

ID=27080513

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA254,945A Expired CA1059140A (fr)	1975-06-23	1976-06-16	2,6-dinitroanilines substituees en -3

Country Status (1)

Country	Link
CA (1)	CA1059140A (fr)

1976
- 1976-06-16 CA CA254,945A patent/CA1059140A/fr not_active Expired

Publication	Publication Date	Title
CA1252642A (fr)	1989-04-18	Preparations contenant des composes heterocycliques et leur utilisation comme herbicides
GB1578852A (en)	1980-11-12	Methods of treating plants and crops with propynylamine derivatives and pesticidal preparations suitable therefor
CS213387B2 (en)	1982-04-09	Herbicide means and method of making the active substances
US3948957A (en)	1976-04-06	3-Azido-2,6-dinitroanilines
DK160454B (da)	1991-03-18	N-benzoyl-n'-pyridyloxyphenylurinstoffer
CS226434B2 (en)	1984-03-19	Herbicide and method of preparing its active substance
EP0124282A1 (fr)	1984-11-07	Bicyclo-oxyaryl-thiourées et procédé de préparation
NZ242756A (en)	1994-07-26	Benzimidazole derivatives having a fused ring which contains 1 or 2 o atoms and at least 1 -cf2- unit; use as fungicides; and precursors
US3819697A (en)	1974-06-25	Substituted phenylurea herbicides
CA1059140A (fr)	1979-07-24	2,6-dinitroanilines substituees en -3
JPH0528220B2 (fr)	1993-04-23
AP36A (en)	1988-12-06	Pyrazoline insecticides
US3764623A (en)	1973-10-09	Herbicidal dinitro-1,3-phenylenediamine compounds
KR940010278B1 (ko)	1994-10-22	살진균성을 갖는 시아노아세트아미도 유도체의 제조방법
US4152460A (en)	1979-05-01	3-Chloro-2,6-dinitro-N-(substituted phenyl)-4-(trifluoromethyl)benzenamines
DE2608488A1 (de)	1976-09-16	Iso(thio)harnstoffe
US3987076A (en)	1976-10-19	2,6-dinitro-3-thiocyanatoanilines
CA1061354A (fr)	1979-08-28	3-cyanamino-2,6-dinitroanilines
US4038403A (en)	1977-07-26	Benzotriazole ovicides and larvicides
KR920005411B1 (ko)	1992-07-03	치환된 테트라졸의 제법
IE43245B1 (en)	1981-01-14	Dinitroanilines
US4331669A (en)	1982-05-25	Fungicidal pyridyl arylureas, compositions containing them and method of controlling fungi and bacteria
US4054603A (en)	1977-10-18	4-Amino-3,5-dinitrobenzenesulfenamides and sulfinamides
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