GB1560709A - Nitrotrifluoromethyl substituted diphenylamines their preparation and rodenticidal compositions - Google Patents
Nitrotrifluoromethyl substituted diphenylamines their preparation and rodenticidal compositions Download PDFInfo
- Publication number
- GB1560709A GB1560709A GB39225/76A GB3922576A GB1560709A GB 1560709 A GB1560709 A GB 1560709A GB 39225/76 A GB39225/76 A GB 39225/76A GB 3922576 A GB3922576 A GB 3922576A GB 1560709 A GB1560709 A GB 1560709A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- dinitro
- bromo
- chloro
- rodenticidal
- 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
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 239000000203 mixture Substances 0.000 title claims description 83
- 230000001119 rodenticidal effect Effects 0.000 title claims description 48
- 238000002360 preparation method Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 19
- 125000005843 halogen group Chemical group 0.000 claims abstract description 12
- 239000003128 rodenticide Substances 0.000 claims abstract description 11
- 241000700159 Rattus Species 0.000 claims description 41
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 30
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 claims description 29
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 28
- 241000699670 Mus sp. Species 0.000 claims description 25
- 125000001153 fluoro group Chemical group F* 0.000 claims description 25
- 241001465754 Metazoa Species 0.000 claims description 21
- 241000283984 Rodentia Species 0.000 claims description 17
- 125000001246 bromo group Chemical group Br* 0.000 claims description 17
- -1 chloro, bromo, iodo, cyano, methyl Chemical group 0.000 claims description 17
- 239000000047 product Substances 0.000 claims description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 13
- 230000035611 feeding Effects 0.000 claims description 12
- 150000002431 hydrogen Chemical group 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 239000003651 drinking water Substances 0.000 claims description 9
- 235000020188 drinking water Nutrition 0.000 claims description 9
- 239000000843 powder Substances 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 239000000969 carrier Substances 0.000 claims description 7
- 235000013339 cereals Nutrition 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 claims description 6
- 235000013305 food Nutrition 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
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- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 2
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- 235000019322 gelatine Nutrition 0.000 claims description 2
- 235000011852 gelatine desserts Nutrition 0.000 claims description 2
- 150000002334 glycols Chemical class 0.000 claims description 2
- 239000003163 gonadal steroid hormone Substances 0.000 claims description 2
- 229940060367 inert ingredients Drugs 0.000 claims description 2
- 239000000787 lecithin Substances 0.000 claims description 2
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- 235000013622 meat product Nutrition 0.000 claims description 2
- 235000013336 milk Nutrition 0.000 claims description 2
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- 210000004080 milk Anatomy 0.000 claims description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims description 2
- 230000000802 nitrating effect Effects 0.000 claims description 2
- 235000021400 peanut butter Nutrition 0.000 claims description 2
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- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 2
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- 230000036515 potency Effects 0.000 claims description 2
- 235000009566 rice Nutrition 0.000 claims description 2
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- 239000004575 stone Substances 0.000 claims description 2
- 235000000346 sugar Nutrition 0.000 claims description 2
- 150000008163 sugars Chemical class 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- 239000002562 thickening agent Substances 0.000 claims description 2
- 239000004559 tracking powder Substances 0.000 claims description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 2
- 239000008158 vegetable oil Substances 0.000 claims description 2
- 239000002699 waste material Substances 0.000 claims description 2
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical class F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 abstract description 8
- 125000001424 substituent group Chemical group 0.000 abstract description 6
- 238000005658 halogenation reaction Methods 0.000 abstract description 5
- 230000026030 halogenation Effects 0.000 abstract description 4
- 239000013543 active substance Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 229940035422 diphenylamine Drugs 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- RXZBYOQLONSTTQ-UHFFFAOYSA-N FCN(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound FCN(C1=CC=CC=C1)C1=CC=CC=C1 RXZBYOQLONSTTQ-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- DQXUPWGUKXGTBG-UHFFFAOYSA-N n-phenyl-n-(trifluoromethyl)aniline Chemical compound C=1C=CC=CC=1N(C(F)(F)F)C1=CC=CC=C1 DQXUPWGUKXGTBG-UHFFFAOYSA-N 0.000 description 6
- 238000006396 nitration reaction Methods 0.000 description 6
- 239000002574 poison Substances 0.000 description 6
- 231100000614 poison Toxicity 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000029936 alkylation Effects 0.000 description 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001448 anilines Chemical class 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 230000001665 lethal effect Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- HHBCEKAWSILOOP-UHFFFAOYSA-N 1,3-dibromo-1,3,5-triazinane-2,4,6-trione Chemical compound BrN1C(=O)NC(=O)N(Br)C1=O HHBCEKAWSILOOP-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- HQROXDLWVGFPDE-UHFFFAOYSA-N 1-chloro-4-nitro-2-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 HQROXDLWVGFPDE-UHFFFAOYSA-N 0.000 description 2
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 2
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- 230000003111 delayed effect Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000002577 pseudohalo group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003476 thallium compounds Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 1
- 229960005080 warfarin Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
- C07C211/56—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- 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
- A01N37/44—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 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/48—Nitro-carboxylic acids; Derivatives thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (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 |
|---|---|---|---|
| US61711575A | 1975-09-26 | 1975-09-26 | |
| US70602276A | 1976-07-21 | 1976-07-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1560709A true GB1560709A (en) | 1980-02-06 |
Family
ID=27087951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB39225/76A Expired GB1560709A (en) | 1975-09-26 | 1976-09-22 | Nitrotrifluoromethyl substituted diphenylamines their preparation and rodenticidal compositions |
Country Status (32)
| Country | Link |
|---|---|
| JP (1) | JPS5828863B2 (pl) |
| AR (1) | AR225588A1 (pl) |
| AT (2) | AT345266B (pl) |
| AU (1) | AU508202B2 (pl) |
| BE (1) | BE846419A (pl) |
| BG (2) | BG27538A3 (pl) |
| BR (1) | BR7606370A (pl) |
| CA (1) | CA1090822A (pl) |
| CH (1) | CH626322A5 (pl) |
| CS (1) | CS189786B2 (pl) |
| DD (2) | DD134431A5 (pl) |
| DE (1) | DE2642148C2 (pl) |
| DK (1) | DK154069C (pl) |
| DZ (1) | DZ85A1 (pl) |
| ES (1) | ES451857A1 (pl) |
| FI (1) | FI62527C (pl) |
| FR (1) | FR2325635A1 (pl) |
| GB (1) | GB1560709A (pl) |
| GR (1) | GR61721B (pl) |
| HU (1) | HU177823B (pl) |
| IE (1) | IE43715B1 (pl) |
| IL (1) | IL50258A (pl) |
| IT (1) | IT1078789B (pl) |
| MX (1) | MX4391E (pl) |
| NL (1) | NL185442C (pl) |
| NO (1) | NO143025C (pl) |
| PH (1) | PH12570A (pl) |
| PL (2) | PL110942B1 (pl) |
| PT (1) | PT65581B (pl) |
| RO (3) | RO75109A (pl) |
| SE (2) | SE435055B (pl) |
| YU (1) | YU43438B (pl) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4215145A (en) | 1978-12-05 | 1980-07-29 | E. I. Du Pont De Nemours And Company | Miticidal, fungicidal, and ovicidal sulfenamides |
| DE3063519D1 (en) * | 1979-09-28 | 1983-07-07 | Ciba Geigy Ag | Polysubstituted diphenyl amines, their preparation and their use |
| US4323580A (en) | 1980-01-24 | 1982-04-06 | E. I. Du Pont De Nemours And Company | Miticidal, fungicidal and ovicidal diphenylsulfenamides |
| JPS56149406A (en) * | 1980-04-21 | 1981-11-19 | Mitsui Toatsu Chem Inc | Production of styrene polymer |
| US4298613A (en) | 1980-05-05 | 1981-11-03 | E. I. Du Pont De Nemours And Company | Agricultural heterocyclic sulfenamides |
| US4341772A (en) * | 1980-05-05 | 1982-07-27 | E. I. Du Pont De Nemours And Company | Agricultural phosphorus-containing sulfenamides |
| US4302451A (en) | 1980-05-05 | 1981-11-24 | E. I. Du Pont De Nemours And Company | Pesticidal phosphorus sulfenamides |
| JPS60206809A (ja) * | 1984-03-29 | 1985-10-18 | Kanegafuchi Chem Ind Co Ltd | 共重合体の製造法 |
| JPS61109460U (pl) * | 1984-12-20 | 1986-07-11 | ||
| CA1287795C (en) * | 1985-12-06 | 1991-08-20 | David G. Hobbs | Composition for rodent control |
| JPS63188675U (pl) * | 1987-05-25 | 1988-12-02 | ||
| JPH0372505A (ja) * | 1989-05-24 | 1991-03-27 | Sanyo Chem Ind Ltd | 電子写真用トナーバインダー |
| JPH0463459U (pl) * | 1990-10-15 | 1992-05-29 | ||
| DE69600907D1 (de) * | 1995-07-18 | 1998-12-10 | Sumitomo Chemical Co | Verfahren zur Kontrolle der Polymerisationsgeschwindigkeit eines Styrolharzes |
| 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 |
| CA2859842C (en) | 2012-03-14 | 2016-11-08 | Sinochem Corporation | Substitute diphenylamine compounds use thereof as antitumor agents |
-
1976
- 1976-08-10 IE IE1765/76A patent/IE43715B1/en not_active IP Right Cessation
- 1976-08-11 GR GR51457A patent/GR61721B/el unknown
- 1976-08-12 IL IL50258A patent/IL50258A/xx unknown
- 1976-08-20 PH PH18820A patent/PH12570A/en unknown
- 1976-08-24 CA CA259,772A patent/CA1090822A/en not_active Expired
- 1976-08-30 MX MX764866U patent/MX4391E/es unknown
- 1976-08-31 AR AR264526A patent/AR225588A1/es active
- 1976-09-01 YU YU2143/76A patent/YU43438B/xx unknown
- 1976-09-09 SE SE7609986A patent/SE435055B/xx not_active IP Right Cessation
- 1976-09-10 PT PT65581A patent/PT65581B/pt unknown
- 1976-09-16 CS CS766024A patent/CS189786B2/cs unknown
- 1976-09-17 RO RO7696216A patent/RO75109A/ro unknown
- 1976-09-17 RO RO7687562A patent/RO70677A/ro unknown
- 1976-09-17 RO RO7696217A patent/RO75110A/ro unknown
- 1976-09-20 DE DE2642148A patent/DE2642148C2/de not_active Expired
- 1976-09-22 GB GB39225/76A patent/GB1560709A/en not_active Expired
- 1976-09-22 BE BE1007640A patent/BE846419A/xx not_active IP Right Cessation
- 1976-09-23 AT AT705576A patent/AT345266B/de not_active IP Right Cessation
- 1976-09-23 FI FI762718A patent/FI62527C/fi not_active IP Right Cessation
- 1976-09-23 CH CH1208076A patent/CH626322A5/de not_active IP Right Cessation
- 1976-09-24 ES ES451857A patent/ES451857A1/es not_active Expired
- 1976-09-24 FR FR7628847A patent/FR2325635A1/fr active Granted
- 1976-09-24 HU HU76EI700A patent/HU177823B/hu unknown
- 1976-09-24 DK DK431076A patent/DK154069C/da not_active IP Right Cessation
- 1976-09-24 BR BR7606370A patent/BR7606370A/pt unknown
- 1976-09-24 NO NO763286A patent/NO143025C/no unknown
- 1976-09-24 BG BG034277A patent/BG27538A3/xx unknown
- 1976-09-24 DD DD76201829A patent/DD134431A5/xx unknown
- 1976-09-24 NL NLAANVRAGE7610602,A patent/NL185442C/xx not_active IP Right Cessation
- 1976-09-24 IT IT27648/76A patent/IT1078789B/it active
- 1976-09-24 DD DD7600194974A patent/DD128782A5/xx unknown
- 1976-09-24 BG BG7639026A patent/BG28701A4/xx unknown
- 1976-09-25 PL PL1976209045A patent/PL110942B1/pl unknown
- 1976-09-25 PL PL1976192654A patent/PL107314B1/pl unknown
- 1976-09-25 JP JP51115319A patent/JPS5828863B2/ja not_active Expired
- 1976-09-27 AU AU18140/76A patent/AU508202B2/en not_active Expired
- 1976-09-27 DZ DZ764292A patent/DZ85A1/fr active
-
1977
- 1977-07-27 AT AT548577A patent/AT361245B/de not_active IP Right Cessation
-
1980
- 1980-09-24 SE SE8006682A patent/SE436392B/sv unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19960921 |