DE2627349A1 - In stellung 3 substituierte 2,6-dinitroaniline - Google Patents
In stellung 3 substituierte 2,6-dinitroanilineInfo
- Publication number
- DE2627349A1 DE2627349A1 DE19762627349 DE2627349A DE2627349A1 DE 2627349 A1 DE2627349 A1 DE 2627349A1 DE 19762627349 DE19762627349 DE 19762627349 DE 2627349 A DE2627349 A DE 2627349A DE 2627349 A1 DE2627349 A1 DE 2627349A1
- Authority
- DE
- Germany
- Prior art keywords
- dinitro
- formula
- alkyl
- trifluoromethylaniline
- chloro
- 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.)
- Withdrawn
Links
- QFUSCYRJMXLNRB-UHFFFAOYSA-N 2,6-dinitroaniline Chemical group NC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O QFUSCYRJMXLNRB-UHFFFAOYSA-N 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 60
- 238000002360 preparation method Methods 0.000 claims description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 22
- 239000004480 active ingredient Substances 0.000 claims description 13
- -1 alkali metal salts Chemical class 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 3
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims description 3
- 239000000417 fungicide Substances 0.000 claims description 3
- 229940080818 propionamide Drugs 0.000 claims description 3
- 229910052979 sodium sulfide Inorganic materials 0.000 claims description 3
- 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 description 2
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 claims 2
- VNSRCCYGYHELNR-UHFFFAOYSA-N [3-(diethylamino)-2,4-dinitro-6-(trifluoromethyl)phenyl]cyanamide Chemical compound CCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(NC#N)=C1[N+]([O-])=O VNSRCCYGYHELNR-UHFFFAOYSA-N 0.000 claims 1
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 9
- 239000005457 ice water Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- FDSBMUJBQJNCNW-UHFFFAOYSA-N 3-chloro-2,6-dinitroaniline Chemical compound NC1=C([N+]([O-])=O)C=CC(Cl)=C1[N+]([O-])=O FDSBMUJBQJNCNW-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000011835 investigation Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 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 4
- 239000003513 alkali Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000000428 dust Substances 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000219094 Vitaceae Species 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 235000021021 grapes Nutrition 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- VLRGXXKFHVJQOL-UHFFFAOYSA-N 3-chloropentane-2,4-dione Chemical compound CC(=O)C(Cl)C(C)=O VLRGXXKFHVJQOL-UHFFFAOYSA-N 0.000 description 2
- FCTXEFOUDMXDPD-UHFFFAOYSA-N 3-sulfanylpropanenitrile Chemical compound SCCC#N FCTXEFOUDMXDPD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 241001281803 Plasmopara viticola Species 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- IBORVNWWBXIDQY-UHFFFAOYSA-N [2,4-dinitro-3-(pentan-3-ylamino)-6-(trifluoromethyl)phenyl]cyanamide Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C(F)(F)F)C(NC#N)=C1[N+]([O-])=O IBORVNWWBXIDQY-UHFFFAOYSA-N 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229910052903 pyrophyllite Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 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
- 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
- VHRLDDTWBHYSSP-UHFFFAOYSA-N 1-(4-bromo-2,6-dinitrophenyl)piperidine Chemical compound [O-][N+](=O)C1=CC(Br)=CC([N+]([O-])=O)=C1N1CCCCC1 VHRLDDTWBHYSSP-UHFFFAOYSA-N 0.000 description 1
- SRISDGGKWIAQMK-UHFFFAOYSA-N 1-(4-iodo-2,6-dinitrophenyl)piperidine Chemical compound [O-][N+](=O)C1=CC(I)=CC([N+]([O-])=O)=C1N1CCCCC1 SRISDGGKWIAQMK-UHFFFAOYSA-N 0.000 description 1
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-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
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 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
- 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
- YPGYIKOXQRDUSU-UHFFFAOYSA-N CCCN(CCCl)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(NC#N)=C1[N+]([O-])=O Chemical compound CCCN(CCCl)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(NC#N)=C1[N+]([O-])=O YPGYIKOXQRDUSU-UHFFFAOYSA-N 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- 235000009161 Espostoa lanata Nutrition 0.000 description 1
- 240000001624 Espostoa lanata Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 101100518501 Mus musculus Spp1 gene Proteins 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 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
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- JAQPHQWHIMECHP-UHFFFAOYSA-N [3-(butan-2-ylamino)-2,4-dinitro-6-(trifluoromethyl)phenyl]cyanamide Chemical compound CCC(C)NC1=C([N+]([O-])=O)C=C(C(F)(F)F)C(NC#N)=C1[N+]([O-])=O JAQPHQWHIMECHP-UHFFFAOYSA-N 0.000 description 1
- VOKZMBQHPDGBLX-UHFFFAOYSA-N [3-(dimethylamino)-2,4-dinitro-6-(trifluoromethyl)phenyl] thiocyanate Chemical compound CN(C)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(SC#N)=C1[N+]([O-])=O VOKZMBQHPDGBLX-UHFFFAOYSA-N 0.000 description 1
- YZPDKRCOMWRSRK-UHFFFAOYSA-N [3-(methylamino)-2,4-dinitro-6-(trifluoromethyl)phenyl] thiocyanate Chemical compound CNC1=C([N+]([O-])=O)C=C(C(F)(F)F)C(SC#N)=C1[N+]([O-])=O YZPDKRCOMWRSRK-UHFFFAOYSA-N 0.000 description 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 description 1
- HRIAICCWMXAVBU-UHFFFAOYSA-N [N+](=O)([O-])C1=C(N(CC2OCCC2)C)C(=CC(=C1SC#N)C(F)(F)F)[N+](=O)[O-] Chemical compound [N+](=O)([O-])C1=C(N(CC2OCCC2)C)C(=CC(=C1SC#N)C(F)(F)F)[N+](=O)[O-] HRIAICCWMXAVBU-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 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
- 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
- 230000015572 biosynthetic process Effects 0.000 description 1
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- 239000012973 diazabicyclooctane Substances 0.000 description 1
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- 230000002538 fungal effect Effects 0.000 description 1
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- 235000002532 grape seed extract Nutrition 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
- 229920000940 maneb Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 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
- 125000005394 methallyl group Chemical group 0.000 description 1
- 150000004704 methoxides Chemical class 0.000 description 1
- MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 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
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 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
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/28—Nitrogen atoms
- C07D295/30—Nitrogen atoms non-acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido 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
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/50—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no 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
- C07D307/22—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58931275A | 1975-06-23 | 1975-06-23 | |
| US05/589,314 US3948957A (en) | 1975-06-23 | 1975-06-23 | 3-Azido-2,6-dinitroanilines |
| US05/589,313 US3979453A (en) | 1975-06-23 | 1975-06-23 | 3-Cyanamino-2,6-dinitroanilines |
| US05/589,315 US3987076A (en) | 1975-06-23 | 1975-06-23 | 2,6-dinitro-3-thiocyanatoanilines |
| US66836076A | 1976-03-19 | 1976-03-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2627349A1 true DE2627349A1 (de) | 1977-01-13 |
Family
ID=27541953
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762627349 Withdrawn DE2627349A1 (de) | 1975-06-23 | 1976-06-18 | In stellung 3 substituierte 2,6-dinitroaniline |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS525716A (enExample) |
| AR (1) | AR217403A1 (enExample) |
| AU (1) | AU501747B2 (enExample) |
| BE (1) | BE843235A (enExample) |
| BG (1) | BG25510A3 (enExample) |
| BR (1) | BR7604090A (enExample) |
| DE (1) | DE2627349A1 (enExample) |
| FR (1) | FR2336391A1 (enExample) |
| GB (1) | GB1548666A (enExample) |
| GR (1) | GR60351B (enExample) |
| IE (1) | IE43245B1 (enExample) |
| IL (1) | IL49813A (enExample) |
| IT (1) | IT1060865B (enExample) |
| NL (1) | NL7606743A (enExample) |
| RO (2) | RO76214A (enExample) |
| TR (1) | TR19721A (enExample) |
| YU (1) | YU147876A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4259347A (en) * | 1978-02-16 | 1981-03-31 | Eli Lilly And Company | Control of phytopathogens using dinitroaniline compounds |
| JPS62289120A (ja) * | 1986-06-05 | 1987-12-16 | レインボ−薬品株式会社 | 園芸用植物生育装置 |
-
1976
- 1976-06-15 GR GR50991A patent/GR60351B/el unknown
- 1976-06-15 AR AR263621A patent/AR217403A1/es active
- 1976-06-16 YU YU01478/76A patent/YU147876A/xx unknown
- 1976-06-16 IL IL49813A patent/IL49813A/xx unknown
- 1976-06-17 RO RO7695777A patent/RO76214A/ro unknown
- 1976-06-17 TR TR19721A patent/TR19721A/xx unknown
- 1976-06-17 RO RO7595778A patent/RO76215A/ro unknown
- 1976-06-18 DE DE19762627349 patent/DE2627349A1/de not_active Withdrawn
- 1976-06-21 IT IT24498/76A patent/IT1060865B/it active
- 1976-06-22 GB GB25859/76A patent/GB1548666A/en not_active Expired
- 1976-06-22 IE IE1346/76A patent/IE43245B1/en unknown
- 1976-06-22 BG BG033555A patent/BG25510A3/xx unknown
- 1976-06-22 NL NL7606743A patent/NL7606743A/xx not_active Application Discontinuation
- 1976-06-22 BE BE1007467A patent/BE843235A/xx unknown
- 1976-06-23 JP JP51075952A patent/JPS525716A/ja active Pending
- 1976-06-23 BR BR7604090A patent/BR7604090A/pt unknown
- 1976-06-23 AU AU15206/76A patent/AU501747B2/en not_active Expired
- 1976-06-23 FR FR7619082A patent/FR2336391A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| TR19721A (tr) | 1979-10-16 |
| AU501747B2 (en) | 1979-06-28 |
| IE43245B1 (en) | 1981-01-14 |
| AU1520676A (en) | 1978-01-05 |
| YU147876A (en) | 1982-02-28 |
| GB1548666A (en) | 1979-07-18 |
| FR2336391A1 (fr) | 1977-07-22 |
| BR7604090A (pt) | 1977-07-05 |
| IE43245L (en) | 1976-12-23 |
| IL49813A0 (en) | 1976-08-31 |
| IL49813A (en) | 1979-11-30 |
| NL7606743A (nl) | 1976-12-27 |
| IT1060865B (it) | 1982-09-30 |
| BE843235A (fr) | 1976-12-22 |
| AR217403A1 (es) | 1980-03-31 |
| JPS525716A (en) | 1977-01-17 |
| RO76215A (ro) | 1981-02-28 |
| BG25510A3 (en) | 1978-10-10 |
| FR2336391B1 (enExample) | 1979-07-20 |
| GR60351B (en) | 1978-05-18 |
| RO76214A (ro) | 1981-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |