SE436392B - RODENTICID COMPOSITION CONTAINING AS ACTIVE INGREDIENT CERTAIN DIFENYLAMINE COMPOUNDS - Google Patents
RODENTICID COMPOSITION CONTAINING AS ACTIVE INGREDIENT CERTAIN DIFENYLAMINE COMPOUNDSInfo
- Publication number
- SE436392B SE436392B SE8006682A SE8006682A SE436392B SE 436392 B SE436392 B SE 436392B SE 8006682 A SE8006682 A SE 8006682A SE 8006682 A SE8006682 A SE 8006682A SE 436392 B SE436392 B SE 436392B
- Authority
- SE
- Sweden
- Prior art keywords
- composition
- compounds
- symbol
- active ingredient
- bromine
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 16
- 239000004480 active ingredient Substances 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 title description 22
- DMBHHRLKUKUOEG-UHFFFAOYSA-N N-phenyl aniline Natural products C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 11
- 230000001119 rodenticidal effect Effects 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Chemical group 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 241000700159 Rattus Species 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 241000699670 Mus sp. Species 0.000 claims description 4
- 241000283984 Rodentia Species 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- -1 diphenylamine compound Chemical class 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000003128 rodenticide Substances 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000000796 flavoring agent Substances 0.000 claims 1
- 235000019634 flavors Nutrition 0.000 claims 1
- 239000003205 fragrance Substances 0.000 claims 1
- 239000003163 gonadal steroid hormone Substances 0.000 claims 1
- 238000000034 method Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- RLXKADBMLQPLDV-UHFFFAOYSA-N 2-chloro-1,5-dinitro-3-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(Cl)C(C(F)(F)F)=C1 RLXKADBMLQPLDV-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
- 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)
Description
dïßdfâëdâ s 2 2 Tertiära difenylaminer sådana som föreningarna med nedanstående formel I har icke tidigare beskrivits. Det är emellertid känt att vissa sekundära difenylaminer har fungicid och insekticid verkan. Rodenticida difenylaminer har icke tidi- gare varit kända; I den brittiska patentskriften 868 165 anges di- fenylaminföreningar med en mycket omfattande allmän formel. dïßdfâëdâ s 2 2 Tertiary diphenylamines such as the compounds of formula I below have not been previously described. However, it is known that some secondary diphenylamines have fungicidal and insecticidal activity. Rodenticidal diphenylamines have not been previously known; British Patent Specification 868 165 discloses diphenylamine compounds having a very comprehensive general formula.
Ingen av de specifikt framställda föreningarna omfattas dock av nedanstående formel I.However, none of the specifically prepared compounds are covered by the following formula I.
I FR 2 211 450, DE 2 213 081 och De 2 509 416 be- skrives sekundära difenylaminer, vilka innehåller gruppen -NH-, 'medan föreningarna med nedanstående formel I är tertiära dife- nylaminer, vilka innehåller gruppen -N-. De nya föreningarna alkyl med nedanstående formel I har rodenticid verkan, medan de kända närbesläktade föreningarna har helt andra pesticida egenskaper, såsom insekticid, akaricid och fungicid verkan.FR 2 211 450, DE 2 213 081 and De 2 509 416 describe secondary diphenylamines which contain the group -NH-, 'while the compounds of the formula I below are tertiary diphenylamines which contain the group -N-. The new alkyl compounds of the following formula I have rodenticidal action, while the known closely related compounds have completely different pesticidal properties, such as insecticidal, acaricidal and fungicidal action.
Såsom nämnts beskriver de franska och tyska publi- kationerna enbart NH-derivat (sekundära difenylaminer), och näs- tan alla de enligt den brittiska patentskriften specifikt fram- ställda föreningarna är också NH-derivat. Vi har överraskande funnit att alkylsubstituenten på den centrala kväveatomen i föreningarna med formeln I är kritisk för att gnagare, särskilt råttor, skall acceptera foder innehållande de aktiva föreningar- na. Av hittills okänd anledning accepterar råttor icke foder innehållande HN-difenylaminer, varför sekundära difenylaminer icke är användbara såsom rodenticider.As mentioned, the French and German publications describe only NH derivatives (secondary diphenylamines), and almost all of the compounds specifically prepared according to the British patent specification are also NH derivatives. We have surprisingly found that the alkyl substituent on the central nitrogen atom of the compounds of formula I is critical for rodents, especially rats, to accept feed containing the active compounds. For hitherto unknown reason, rats do not accept feed containing HN-diphenylamines, so secondary diphenylamines are not useful as rodenticides.
Uppfinningen avser sålunda en rodenticid komposi- tion, vilken kännetecknas av att den innefattar en inert bärare och såsom aktiv beståndsdel 5 - 2000 ppm av en difenylaminföre- ning med den allmänna formeln No, RZ OZN Rl (I) 8006682-2 3 där symbolen R betecknar metyl, etyl eller propyl; där symbo- len R1 betecknar klor eller brom; där symbolen R2 betecknar klor eller brom; och där,symbolen R5 betecknar väte, klor eller brom.The invention thus relates to a rodenticidal composition, which is characterized in that it comprises an inert carrier and as active ingredient 5 - 2000 ppm of a diphenylamine compound of the general formula No, R 2 OZN R1 (I) 8006682-2 3 where the symbol R represents methyl, ethyl or propyl; where the symbol R1 represents chlorine or bromine; where the symbol R2 denotes chlorine or bromine; and there, the symbol R5 denotes hydrogen, chlorine or bromine.
Koncentrationen av den aktiva föreningen i kompo- sitionen beror på vilken förening som användes, eftersom före- ningarna har olika kraftig rodenticid verkan, vidare på den snabbhet, med vilken man önskar minska populationen av råttor eller möss, och även på andra faktorer. Om man t.ex. kan iso- lera populationen, så att dess enda födoämneskälla eller vatten- källa är en rodenticid komposition, så bör koncentrationen uppenbarligen vara lägre än om populationen har tillgång till ett antal olika födoämneskällor. De rodenticida kompositioner- na bör vanligen innehålla mellan ca 5 och ca 2000 ppm av den aktiva föreningen. Helst bör man använda koncentrationer av mellan ca 10 och ca 500 ppm, även om naturligtvis mängder både över och under nämnda gränser kan vara verksamma och även önsk- värda i vissa fall.The concentration of the active compound in the composition depends on the compound used, since the compounds have different strong rodenticidal action, further on the rate at which it is desired to reduce the population of rats or mice, and also on other factors. If one e.g. can isolate the population, so that its only food source or water source is a rodenticidal composition, then the concentration should obviously be lower than if the population has access to a number of different food sources. The rodenticidal compositions should generally contain between about 5 and about 2000 ppm of the active compound. Preferably, concentrations of between about 10 and about 500 ppm should be used, although of course amounts both above and below the said limits may be effective and also desirable in some cases.
Den inerta bäraren i kompositionen enligt upp- finningen är företrädesvis ett födoämne. Den aktiva bestånds- delen ingår företrädesvis i kompositionen i en koncentration, som är rodenticidiskt verksam efter två eller flera utford- ringar.The inert carrier in the composition according to the invention is preferably a foodstuff. The active ingredient is preferably included in the composition in a concentration which is rodenticidally active after two or more challenges.
För att minska en population av råttor eller möss anbringar man på en plats som ofta besökes av råttorna eller mössen en rodenticidiskt verksam mängd av en komposition enligt uppfinningen.To reduce a population of rats or mice, a rodenticidally effective amount of a composition of the invention is applied to a site frequently visited by the rats or mice.
De i kompositionerna enligt uppfinningen ingående nya difenylaminföreningarna med formeln I kan framställas genom att (a) en anilinförening med formeln: R n* / \ NHR” (11) :__ s RS .. 16 .J- 1 i dar R betecknar vate, metyl, etyl eller propyl, och R , R och R5 har de ovan angivna betydelserna, omsättes med en 2-halo- 5-nitrobensotrifluoridförening med formeln: $ÛÛ6682 *2 ÛZN -~-' (III) cr, där X betecknar en halogenatom, och R17 betecknar väte eller nitro, med den begränsningen att R16 na R2 och RS betecknar väte, när R17 (b) den i steg (a) erhållna föreningen N-alkyle- och minst en av symboler- betecknar nitro; ras, om R16 betecknar väte; (c) den i steg (b) erhållna föreningen nitreras, R17 betecknar väte; (d) den i steg (c) erhållna föreningen eventuellt halogeneras, om den saknar de önskade halogensubstituenterna.The novel diphenylamine compounds of formula I contained in the compositions of the invention may be prepared by (a) an aniline compound of the formula: R n * / \ NHR '(11): __ s RS .. 16. methyl, ethyl or propyl, and R, R and R5 have the meanings given above, reacted with a 2-halo-5-nitrobenzotrifluoride compound of the formula: (III) cr, where X represents a halogen atom , and R 17 represents hydrogen or nitro, with the proviso that R 16 and R 2 and R 5 represent hydrogen, when R 17 (b) the compound obtained in step (a) represents N-alkyl- and at least one of the symbols- represents nitro; race, if R16 represents hydrogen; (c) the compound obtained in step (b) is nitrated, R 17 represents hydrogen; (d) the compound obtained in step (c) is optionally halogenated, if it lacks the desired halogen substituents.
De föredragna föreningarna med formeln I är de föreningar, där R betecknar metyl, och de föreningar, där R1, R2 och R5 betecknar klor eller brom.The preferred compounds of formula I are those compounds wherein R represents methyl and those compounds wherein R 1, R 2 and R 5 represent chlorine or bromine.
De nya föreningarna med formeln I kan icke fram- ställas enligt enkla direkta metoder, utan de måste framställas enligt ett flerstegsförfarande. Man skulle kunna vänta sig, Om att föreningarna ksulle kunna syntetiseras genom direkt omsätt- ning av en substituerad N~alkylanilin med 2-klor-3, 5-dinitro- bensotrifluorid. Man skulle även kunna vänta sig, att det skul- le vara möjligt att först framställa motsvarande N-H-difenyl- amin och därefter alkylera kvävet med alkyljodid eller något liknande alkyleringsmedel. Förutom när det gäller de föreningar, vilka har antingen 2-ställningen eller 6-ställningen osubstitue- rad, har det emellertid visat sig, att ingen av dessa metoder är användbar. För det stora flertalet av föreningarna måste framställningen ske enligt någon av de nedan angivna utförings- formerna. ~. -. ,_._._......- ___._____.... i V_l_.___._.._, 8006682-2 5 Utförïngsform A . R? I' IF 02Nha1o+H - N / \>_R“ ___-_- CFa Rio - RT O2N halo+ H2N R“--- » CF3 nl” R7 H l om N RS RIU CF3 R7 R / \\ x OZN \ N RE CFS E10 I i eventuell T I T s produkt <&-- nitrepinq 1 ø 40 $Ûü6632°°2 6 I ovanstående formler har symbolerna R6, R7, R1O, samma betydelser som symbolerna R1, R2 respektive Rs, eller vilka som helst av symbolerna kan beteckna väte. Förfarandet kan genomföras utgående från en anilin, vilken uppbär några av eller alla de i produkten önskade substituenterna R1, R och R5, eller utgående från en osubstituerad anilin beroende på vilka substituenter som önskas i produkten. Halogensubstituenter på anilinringen kan införas vid slutet av processen.The new compounds of formula I cannot be prepared by simple direct methods, but must be prepared according to a multi-step procedure. It could be expected that the compounds could be synthesized by direct reaction of a substituted N-alkylaniline with 2-chloro-3,5-dinitrobenzotrifluoride. It could also be expected that it would be possible to first prepare the corresponding N-H-diphenylamine and then alkylate the nitrogen with alkyl iodide or some similar alkylating agent. However, except for those compounds which have either the 2-position or the 6-position unsubstituted, it has been found that none of these methods is useful. For the vast majority of the compounds, the preparation must take place according to one of the embodiments given below. ~. -. , _._._......- ___._____.... i V_l _.___._.._, 8006682-2 5 Embodiment A. R? I 'IF 02Nha1o + H - N / \> _ R “___-_- CFa Rio - RT O2N halo + H2N R“ --- »CF3 nl” R7 H l om N RS RIU CF3 R7 R / \\ x OZN \ N RE CFS E10 I in any TIT's product <& - nitrepinq 1 ø 40 $ Ûü6632 °° 2 6 In the above formulas, the symbols R6, R7, R1O, have the same meanings as the symbols R1, R2 and Rs, or any of the symbols may denote hydrogen. The process can be carried out starting from an aniline, which bears some or all of the substituents R1, R and R5 desired in the product, or starting from an unsubstituted aniline depending on which substituents are desired in the product. Halogen substituents on the aniline ring can be introduced at the end of the process.
Utföringsform B N02 Rlz OzN halo + Hz R1 1 '_-“ 1s cr; R N02 Ria ïEmbodiment B NO 2 R 12 O 2 N halo + Hz R1 1 '_- “1s cr; R N02 Ria ï
Claims (2)
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 (2)
| Publication Number | Publication Date |
|---|---|
| SE8006682L SE8006682L (en) | 1980-09-24 |
| SE436392B true SE436392B (en) | 1984-12-10 |
Family
ID=27087951
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7609986A SE435055B (en) | 1975-09-26 | 1976-09-09 | N-ALKYLDIFENYLAMINE DERIVATIVES WITH RODENTICID EFFECT AND USE THEREOF FOR THE CONTROL OF RATTOR AND MOSS |
| SE8006682A SE436392B (en) | 1975-09-26 | 1980-09-24 | RODENTICID COMPOSITION CONTAINING AS ACTIVE INGREDIENT CERTAIN DIFENYLAMINE COMPOUNDS |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7609986A SE435055B (en) | 1975-09-26 | 1976-09-09 | N-ALKYLDIFENYLAMINE DERIVATIVES WITH RODENTICID EFFECT AND USE THEREOF FOR THE CONTROL OF RATTOR AND MOSS |
Country Status (32)
| Country | Link |
|---|---|
| JP (1) | JPS5828863B2 (en) |
| AR (1) | AR225588A1 (en) |
| AT (2) | AT345266B (en) |
| AU (1) | AU508202B2 (en) |
| BE (1) | BE846419A (en) |
| BG (2) | BG28701A4 (en) |
| BR (1) | BR7606370A (en) |
| CA (1) | CA1090822A (en) |
| CH (1) | CH626322A5 (en) |
| CS (1) | CS189786B2 (en) |
| DD (2) | DD128782A5 (en) |
| DE (1) | DE2642148C2 (en) |
| DK (1) | DK154069C (en) |
| DZ (1) | DZ85A1 (en) |
| ES (1) | ES451857A1 (en) |
| FI (1) | FI62527C (en) |
| FR (1) | FR2325635A1 (en) |
| GB (1) | GB1560709A (en) |
| GR (1) | GR61721B (en) |
| HU (1) | HU177823B (en) |
| IE (1) | IE43715B1 (en) |
| IL (1) | IL50258A (en) |
| IT (1) | IT1078789B (en) |
| MX (1) | MX4391E (en) |
| NL (1) | NL185442C (en) |
| NO (1) | NO143025C (en) |
| PH (1) | PH12570A (en) |
| PL (2) | PL110942B1 (en) |
| PT (1) | PT65581B (en) |
| RO (3) | RO75110A (en) |
| SE (2) | SE435055B (en) |
| YU (1) | YU43438B (en) |
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 |
| EP0026743B1 (en) * | 1979-09-28 | 1983-05-25 | 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 |
| US4302451A (en) | 1980-05-05 | 1981-11-24 | E. I. Du Pont De Nemours And Company | Pesticidal phosphorus sulfenamides |
| US4341772A (en) * | 1980-05-05 | 1982-07-27 | E. I. Du Pont De Nemours And Company | Agricultural phosphorus-containing sulfenamides |
| US4298613A (en) | 1980-05-05 | 1981-11-03 | E. I. Du Pont De Nemours And Company | Agricultural heterocyclic sulfenamides |
| JPS60206809A (en) * | 1984-03-29 | 1985-10-18 | Kanegafuchi Chem Ind Co Ltd | Production of copolymer |
| JPS61109460U (en) * | 1984-12-20 | 1986-07-11 | ||
| CA1287795C (en) * | 1985-12-06 | 1991-08-20 | David G. Hobbs | Composition for rodent control |
| JPS63188675U (en) * | 1987-05-25 | 1988-12-02 | ||
| JPH0372505A (en) * | 1989-05-24 | 1991-03-27 | Sanyo Chem Ind Ltd | Binder for electrophotographic toner |
| JPH0463459U (en) * | 1990-10-15 | 1992-05-29 | ||
| BR9603106A (en) * | 1995-07-18 | 1998-05-05 | Sumitomo Chemical Co | Process for controlling a polymerization rate and continuous polymerization process |
| CN102199095B (en) | 2010-03-22 | 2014-04-09 | 中国中化股份有限公司 | Substituted diphenylamine compounds and preparation and application thereof |
| 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/en unknown
- 1976-08-12 IL IL50258A patent/IL50258A/en 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/en unknown
- 1976-08-31 AR AR264526A patent/AR225588A1/en active
- 1976-09-01 YU YU2143/76A patent/YU43438B/en unknown
- 1976-09-09 SE SE7609986A patent/SE435055B/en not_active IP Right Cessation
- 1976-09-10 PT PT65581A patent/PT65581B/en unknown
- 1976-09-16 CS CS766024A patent/CS189786B2/en unknown
- 1976-09-17 RO RO7696217A patent/RO75110A/en unknown
- 1976-09-17 RO RO7696216A patent/RO75109A/en unknown
- 1976-09-17 RO RO7687562A patent/RO70677A/en unknown
- 1976-09-20 DE DE2642148A patent/DE2642148C2/en not_active Expired
- 1976-09-22 GB GB39225/76A patent/GB1560709A/en not_active Expired
- 1976-09-22 BE BE1007640A patent/BE846419A/en not_active IP Right Cessation
- 1976-09-23 FI FI762718A patent/FI62527C/en not_active IP Right Cessation
- 1976-09-23 CH CH1208076A patent/CH626322A5/en not_active IP Right Cessation
- 1976-09-23 AT AT705576A patent/AT345266B/en not_active IP Right Cessation
- 1976-09-24 IT IT27648/76A patent/IT1078789B/en active
- 1976-09-24 FR FR7628847A patent/FR2325635A1/en active Granted
- 1976-09-24 BG BG7639026A patent/BG28701A4/en unknown
- 1976-09-24 ES ES451857A patent/ES451857A1/en not_active Expired
- 1976-09-24 HU HU76EI700A patent/HU177823B/en unknown
- 1976-09-24 DD DD7600194974A patent/DD128782A5/en unknown
- 1976-09-24 NO NO763286A patent/NO143025C/en unknown
- 1976-09-24 NL NLAANVRAGE7610602,A patent/NL185442C/en not_active IP Right Cessation
- 1976-09-24 DK DK431076A patent/DK154069C/en not_active IP Right Cessation
- 1976-09-24 BG BG034277A patent/BG27538A3/en unknown
- 1976-09-24 DD DD76201829A patent/DD134431A5/en unknown
- 1976-09-24 BR BR7606370A patent/BR7606370A/en unknown
- 1976-09-25 PL PL1976209045A patent/PL110942B1/en unknown
- 1976-09-25 JP JP51115319A patent/JPS5828863B2/en not_active Expired
- 1976-09-25 PL PL1976192654A patent/PL107314B1/en unknown
- 1976-09-27 AU AU18140/76A patent/AU508202B2/en not_active Expired
- 1976-09-27 DZ DZ764292A patent/DZ85A1/en active
-
1977
- 1977-07-27 AT AT548577A patent/AT361245B/en not_active IP Right Cessation
-
1980
- 1980-09-24 SE SE8006682A patent/SE436392B/en unknown
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