CA1117548A - 3-chloro-2,6-dinitro-n-(substituted phenyl)-4- (trifluoromethyl) benzenamines - Google Patents
3-chloro-2,6-dinitro-n-(substituted phenyl)-4- (trifluoromethyl) benzenaminesInfo
- Publication number
- CA1117548A CA1117548A CA000319817A CA319817A CA1117548A CA 1117548 A CA1117548 A CA 1117548A CA 000319817 A CA000319817 A CA 000319817A CA 319817 A CA319817 A CA 319817A CA 1117548 A CA1117548 A CA 1117548A
- Authority
- CA
- Canada
- Prior art keywords
- chloro
- compound
- dinitro
- trifluoromethyl
- benzenamine
- 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
- 150000001875 compounds Chemical class 0.000 claims abstract description 72
- 238000000034 method Methods 0.000 claims abstract description 19
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
- 241000233866 Fungi Species 0.000 claims description 12
- 244000000004 fungal plant pathogen Species 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- -1 (2-trifluoromethylphenyl)-3-chloro-2,6-dinitro-4-(trifluoromethyl)benzenamine Chemical compound 0.000 claims description 4
- RFSWJSRTRCBHLE-UHFFFAOYSA-N 3-chloro-2,6-dinitro-4-(trifluoromethyl)-n-[4-(trifluoromethyl)phenyl]aniline Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=CC=C(C(F)(F)F)C=C1 RFSWJSRTRCBHLE-UHFFFAOYSA-N 0.000 claims description 2
- WWNNXBZXFFQHHS-UHFFFAOYSA-N 3-chloro-2,6-dinitro-n-(2,4,6-trichlorophenyl)-4-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=C(Cl)C=C(Cl)C=C1Cl WWNNXBZXFFQHHS-UHFFFAOYSA-N 0.000 claims description 2
- VESAIHREXSGHGR-UHFFFAOYSA-N 3-chloro-2,6-dinitro-n-(3,4,5-trichlorophenyl)-4-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=CC(Cl)=C(Cl)C(Cl)=C1 VESAIHREXSGHGR-UHFFFAOYSA-N 0.000 claims description 2
- IUWLFVDAOQDCGJ-UHFFFAOYSA-N 3-chloro-2,6-dinitro-n-(4-nitrophenyl)-4-(trifluoromethyl)aniline Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC1=C([N+]([O-])=O)C=C(C(F)(F)F)C(Cl)=C1[N+]([O-])=O IUWLFVDAOQDCGJ-UHFFFAOYSA-N 0.000 claims description 2
- VKTXVQFJIIYECZ-UHFFFAOYSA-N 3-chloro-n-(2,4-dichlorophenyl)-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=CC=C(Cl)C=C1Cl VKTXVQFJIIYECZ-UHFFFAOYSA-N 0.000 claims description 2
- LOASZRBFZUUGJE-UHFFFAOYSA-N 3-chloro-n-[4-chloro-3-(trifluoromethyl)phenyl]-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=CC=C(Cl)C(C(F)(F)F)=C1 LOASZRBFZUUGJE-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- ZONOQTUTWQTNMM-UHFFFAOYSA-N n-(2-bromo-4-nitrophenyl)-3-chloro-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound BrC1=CC([N+](=O)[O-])=CC=C1NC1=C([N+]([O-])=O)C=C(C(F)(F)F)C(Cl)=C1[N+]([O-])=O ZONOQTUTWQTNMM-UHFFFAOYSA-N 0.000 claims description 2
- CNFALPOERUKCEG-UHFFFAOYSA-N 3-chloro-2,6-dinitro-n-(2,4,5-trichlorophenyl)-4-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=CC(Cl)=C(Cl)C=C1Cl CNFALPOERUKCEG-UHFFFAOYSA-N 0.000 claims 1
- CSZJYGJYUZIKEI-UHFFFAOYSA-N 3-chloro-2,6-dinitro-n-(2-nitrophenyl)-4-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=C([N+]([O-])=O)C=C(C(F)(F)F)C(Cl)=C1[N+]([O-])=O CSZJYGJYUZIKEI-UHFFFAOYSA-N 0.000 claims 1
- LWJWSJSVFYFNTL-UHFFFAOYSA-N 3-chloro-n-(2-chloro-4-nitrophenyl)-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1NC1=C([N+]([O-])=O)C=C(C(F)(F)F)C(Cl)=C1[N+]([O-])=O LWJWSJSVFYFNTL-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 53
- 229910052801 chlorine Inorganic materials 0.000 abstract description 4
- 230000000855 fungicidal effect Effects 0.000 abstract 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 abstract description 3
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- 238000002844 melting Methods 0.000 description 30
- 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 29
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 238000012360 testing method Methods 0.000 description 21
- 238000009472 formulation Methods 0.000 description 20
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
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- 201000010099 disease Diseases 0.000 description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
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- 239000000725 suspension Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
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- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 6
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- 238000011156 evaluation Methods 0.000 description 5
- 238000005580 one pot reaction Methods 0.000 description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
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- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 2
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- AYTXQERIVRHVNH-UHFFFAOYSA-N n-[3,5-bis(trifluoromethyl)phenyl]-3-chloro-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 AYTXQERIVRHVNH-UHFFFAOYSA-N 0.000 description 2
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- IFLUTKAWZSONNW-UHFFFAOYSA-N 3-chloro-n-(2,5-dibromophenyl)-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=CC(Br)=CC=C1Br IFLUTKAWZSONNW-UHFFFAOYSA-N 0.000 description 1
- MGDAPYKNGYLRKQ-UHFFFAOYSA-N 3-chloro-n-(2,5-dichlorophenyl)-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=CC(Cl)=CC=C1Cl MGDAPYKNGYLRKQ-UHFFFAOYSA-N 0.000 description 1
- KYRXEOHBWWGWIG-UHFFFAOYSA-N 3-chloro-n-(2,6-dibromophenyl)-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=C(Br)C=CC=C1Br KYRXEOHBWWGWIG-UHFFFAOYSA-N 0.000 description 1
- MNRTYHQJFMNVIA-UHFFFAOYSA-N 3-chloro-n-(2,6-dichloro-4-nitrophenyl)-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound ClC1=CC([N+](=O)[O-])=CC(Cl)=C1NC1=C([N+]([O-])=O)C=C(C(F)(F)F)C(Cl)=C1[N+]([O-])=O MNRTYHQJFMNVIA-UHFFFAOYSA-N 0.000 description 1
- WZFOFRISHPCLGD-UHFFFAOYSA-N 3-chloro-n-(2,6-dichlorophenyl)-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=C(Cl)C=CC=C1Cl WZFOFRISHPCLGD-UHFFFAOYSA-N 0.000 description 1
- KSYIQXGBFSISQX-UHFFFAOYSA-N 3-chloro-n-(3,4-dibromophenyl)-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=CC=C(Br)C(Br)=C1 KSYIQXGBFSISQX-UHFFFAOYSA-N 0.000 description 1
- JSTXLMNPQSRGOV-UHFFFAOYSA-N 3-chloro-n-(3,5-dichlorophenyl)-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=CC(Cl)=CC(Cl)=C1 JSTXLMNPQSRGOV-UHFFFAOYSA-N 0.000 description 1
- GDVZWRWTOAZDNN-UHFFFAOYSA-N 3-chloro-n-(3,5-dinitrophenyl)-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC(NC=2C(=C(Cl)C(=CC=2[N+]([O-])=O)C(F)(F)F)[N+]([O-])=O)=C1 GDVZWRWTOAZDNN-UHFFFAOYSA-N 0.000 description 1
- IYFXQLURQKCAAL-UHFFFAOYSA-N 4-[3-chloro-2,6-dinitro-4-(trifluoromethyl)anilino]benzonitrile Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=CC=C(C#N)C=C1 IYFXQLURQKCAAL-UHFFFAOYSA-N 0.000 description 1
- YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- ASPDJZINBYYZRU-UHFFFAOYSA-N 5-amino-2-chlorobenzotrifluoride Chemical compound NC1=CC=C(Cl)C(C(F)(F)F)=C1 ASPDJZINBYYZRU-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- 240000002024 Gossypium herbaceum Species 0.000 description 1
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241000233626 Plasmopara Species 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 1
- 241000082085 Verticillium <Phyllachorales> Species 0.000 description 1
- 241001123669 Verticillium albo-atrum Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000000332 continued effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000035613 defoliation Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- BIXZHMJUSMUDOQ-UHFFFAOYSA-N dichloran Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl BIXZHMJUSMUDOQ-UHFFFAOYSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000013020 final formulation Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 231100001225 mammalian toxicity Toxicity 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- KPFGGEHCIZEMTD-UHFFFAOYSA-N n-chloro-4-nitroaniline Chemical compound [O-][N+](=O)C1=CC=C(NCl)C=C1 KPFGGEHCIZEMTD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 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
- 239000003415 peat Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/18—Nitro compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/34—Nitriles
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/873,190 US4152460A (en) | 1978-01-30 | 1978-01-30 | 3-Chloro-2,6-dinitro-N-(substituted phenyl)-4-(trifluoromethyl)benzenamines |
| US873,190 | 1978-01-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1117548A true CA1117548A (en) | 1982-02-02 |
Family
ID=25361144
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000319817A Expired CA1117548A (en) | 1978-01-30 | 1979-01-17 | 3-chloro-2,6-dinitro-n-(substituted phenyl)-4- (trifluoromethyl) benzenamines |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US4152460A (en]) |
| EP (1) | EP0003430B1 (en]) |
| JP (1) | JPS54109931A (en]) |
| AR (1) | AR223472A1 (en]) |
| AT (1) | AT362962B (en]) |
| AU (1) | AU525301B2 (en]) |
| BE (1) | BE873550A (en]) |
| BR (1) | BR7900462A (en]) |
| CA (1) | CA1117548A (en]) |
| CH (1) | CH635568A5 (en]) |
| CS (1) | CS201022B2 (en]) |
| DD (1) | DD141772A5 (en]) |
| DE (1) | DE2961728D1 (en]) |
| DK (1) | DK36479A (en]) |
| EG (1) | EG13874A (en]) |
| ES (1) | ES477214A1 (en]) |
| FI (1) | FI66348C (en]) |
| FR (1) | FR2415619A1 (en]) |
| GB (1) | GB2013197B (en]) |
| GR (1) | GR72749B (en]) |
| GT (1) | GT197955866A (en]) |
| HU (1) | HU181430B (en]) |
| IE (1) | IE47988B1 (en]) |
| IL (1) | IL56443A (en]) |
| LU (1) | LU80828A1 (en]) |
| MX (1) | MX5371E (en]) |
| NZ (1) | NZ189410A (en]) |
| PH (1) | PH15211A (en]) |
| PL (1) | PL117491B1 (en]) |
| PT (1) | PT69086A (en]) |
| RO (1) | RO76486A (en]) |
| SU (1) | SU990080A3 (en]) |
| ZA (1) | ZA79344B (en]) |
Families Citing this family (6)
| 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 |
| US4309425A (en) * | 1979-08-24 | 1982-01-05 | E. I. Du Pont De Nemours And Company | Miticidal, insecticidal, ovicidal and fungicidal N-(N',N'-diarylaminothio)sulfonamides |
| IL61776A (en) * | 1980-01-08 | 1984-05-31 | Lilly Co Eli | N-(nitrophenyl)-polyfluoroethoxy-benzenamines,their preparation,fungicidal and anticoccidial methods using them |
| CN102199095B (zh) | 2010-03-22 | 2014-04-09 | 中国中化股份有限公司 | 一种取代二苯胺类化合物及其制备与应用 |
| WO2013135147A1 (zh) | 2012-03-14 | 2013-09-19 | 中国中化股份有限公司 | 取代二苯胺类化合物作为制备抗肿瘤药物的应用 |
| CN108976167B (zh) * | 2017-06-02 | 2021-12-07 | 沈阳中化农药化工研发有限公司 | 一种取代苯肼类化合物及其应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3764624A (en) * | 1970-08-05 | 1973-10-09 | United States Borax Chem | N-substituted-2,6-dinitro-3-(alkoxy or alkylthio)-4-substituted-aniline compounds |
| GB1405120A (en) * | 1972-12-20 | 1975-09-03 | Ici Ltd | Nitrobenzene derivatives |
| US3950377A (en) * | 1972-12-20 | 1976-04-13 | Imperial Chemical Industries Limited | Diphenylamine derivatives |
-
1978
- 1978-01-30 US US05/873,190 patent/US4152460A/en not_active Expired - Lifetime
-
1979
- 1979-01-17 AR AR275200A patent/AR223472A1/es active
- 1979-01-17 CA CA000319817A patent/CA1117548A/en not_active Expired
- 1979-01-17 NZ NZ189410A patent/NZ189410A/xx unknown
- 1979-01-17 FR FR7901112A patent/FR2415619A1/fr active Granted
- 1979-01-17 FI FI790141A patent/FI66348C/fi not_active IP Right Cessation
- 1979-01-17 IL IL56443A patent/IL56443A/xx unknown
- 1979-01-17 PT PT7969086A patent/PT69086A/pt unknown
- 1979-01-18 GT GT197955866A patent/GT197955866A/es unknown
- 1979-01-18 BE BE1/9245A patent/BE873550A/xx not_active IP Right Cessation
- 1979-01-19 PH PH22087A patent/PH15211A/en unknown
- 1979-01-22 JP JP651879A patent/JPS54109931A/ja active Pending
- 1979-01-23 RO RO7996360A patent/RO76486A/ro unknown
- 1979-01-24 CH CH72079A patent/CH635568A5/fr not_active IP Right Cessation
- 1979-01-24 PL PL1979212966A patent/PL117491B1/pl unknown
- 1979-01-24 EP EP79300123A patent/EP0003430B1/en not_active Expired
- 1979-01-24 GB GB7902584A patent/GB2013197B/en not_active Expired
- 1979-01-24 DE DE7979300123T patent/DE2961728D1/de not_active Expired
- 1979-01-25 BR BR7900462A patent/BR7900462A/pt unknown
- 1979-01-26 LU LU80828A patent/LU80828A1/xx unknown
- 1979-01-26 ZA ZA79344A patent/ZA79344B/xx unknown
- 1979-01-26 AT AT0060779A patent/AT362962B/de not_active IP Right Cessation
- 1979-01-26 HU HU79EI838A patent/HU181430B/hu unknown
- 1979-01-26 ES ES477214A patent/ES477214A1/es not_active Expired
- 1979-01-26 AU AU43727/79A patent/AU525301B2/en not_active Ceased
- 1979-01-27 EG EG56/79A patent/EG13874A/xx active
- 1979-01-29 GR GR58203A patent/GR72749B/el unknown
- 1979-01-29 SU SU792714351A patent/SU990080A3/ru active
- 1979-01-29 DK DK36479A patent/DK36479A/da not_active Application Discontinuation
- 1979-01-29 MX MX797689U patent/MX5371E/es unknown
- 1979-01-30 CS CS79656A patent/CS201022B2/cs unknown
- 1979-01-30 IE IE15379A patent/IE47988B1/en unknown
- 1979-01-30 DD DD79210715A patent/DD141772A5/de unknown
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| Date | Code | Title | Description |
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| MKEX | Expiry |