DE2041734A1 - Carbamate der 2-Phenylhydrazino-2-imidazoline,Verfahren zu ihrer Herstellung und ihre Verwendung als Ektoparasitizide - Google Patents
Carbamate der 2-Phenylhydrazino-2-imidazoline,Verfahren zu ihrer Herstellung und ihre Verwendung als EktoparasitizideInfo
- Publication number
- DE2041734A1 DE2041734A1 DE19702041734 DE2041734A DE2041734A1 DE 2041734 A1 DE2041734 A1 DE 2041734A1 DE 19702041734 DE19702041734 DE 19702041734 DE 2041734 A DE2041734 A DE 2041734A DE 2041734 A1 DE2041734 A1 DE 2041734A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- stands
- carbon atoms
- bromine
- chlorine
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 9
- AJAGPIBJNAJXBS-UHFFFAOYSA-N 1-(4,5-dihydroimidazol-1-yl)-2-phenylhydrazine Chemical class C1=NCCN1NNC1=CC=CC=C1 AJAGPIBJNAJXBS-UHFFFAOYSA-N 0.000 title claims description 7
- 150000004657 carbamic acid derivatives Chemical class 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000013057 ectoparasiticide Substances 0.000 title description 3
- -1 alkyl radical Chemical class 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 230000001984 ectoparasiticidal effect Effects 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 241000238876 Acari Species 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 230000003151 ovacidal effect Effects 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 241000238680 Rhipicephalus microplus Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 241001481703 Rhipicephalus <genus> Species 0.000 description 4
- 244000078703 ectoparasite Species 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 235000015278 beef Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- MBCXBZSORKCJSZ-UHFFFAOYSA-N 1-(4,5-dihydro-1H-imidazol-2-yl)-1-phenylhydrazine hydrobromide Chemical compound Br.C1(=CC=CC=C1)N(N)C=1NCCN1 MBCXBZSORKCJSZ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 241000238679 Amblyomma Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 241001480803 Hyalomma Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000238889 Ixodidae Species 0.000 description 1
- 241000771994 Melophagus ovinus Species 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241001649230 Psoroptes ovis Species 0.000 description 1
- 241000864246 Rhipicephalus decoloratus Species 0.000 description 1
- 241000509418 Sarcoptidae Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical class NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 230000017448 oviposition Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 238000009304 pastoral farming Methods 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- QQKDTTWZXHEGAQ-UHFFFAOYSA-N propyl carbonochloridate Chemical compound CCCOC(Cl)=O QQKDTTWZXHEGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/52—Nitrogen atoms not forming part of a nitro radical with hetero atoms directly attached to said nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702041734 DE2041734A1 (de) | 1970-08-22 | 1970-08-22 | Carbamate der 2-Phenylhydrazino-2-imidazoline,Verfahren zu ihrer Herstellung und ihre Verwendung als Ektoparasitizide |
| US00173290A US3755351A (en) | 1970-08-22 | 1971-08-19 | Carbamates of 2-phenylhydrazino-2-imidazolines |
| NL7111460A NL7111460A (enExample) | 1970-08-22 | 1971-08-19 | |
| FR7130452A FR2104611A5 (enExample) | 1970-08-22 | 1971-08-20 | |
| CA121,016A CA939360A (en) | 1970-08-22 | 1971-08-20 | Carbamates of 2-phenylhydrazino-2-imidazolines and processes for their preparation and use |
| BE771583A BE771583A (fr) | 1970-08-22 | 1971-08-20 | Nouveaux carbamates de 2-phenylhydrazino-2-imidazolines, leur procede de preparation et leur utilisation comme ectoparasiticides |
| AU32609/71A AU462408B2 (en) | 1970-08-22 | 1971-08-20 | Carbamates of 2-phenylhydrazino-2-imidazolines processes for their manufacture, and their use as ectoparasiticides |
| AT731571A AT316577B (de) | 1970-08-22 | 1971-08-20 | Verfahren zur Herstellung von neuen 2-[N<1>-(Alkoxycarbonyl)-N<2>-(phenyl)-hydrazino]-2-imidazolinen und deren Säureadditionssalzen |
| DK410371AA DK130904B (da) | 1970-08-22 | 1971-08-20 | Ektoparasiticidt middel indeholdende carbazinsyreestere. |
| IL37534A IL37534A (en) | 1970-08-22 | 1971-08-20 | N1-alkoxycarbonyl-n2-phenylhydrazino-2-imidazolines,processes for their manufacture,and their use as ectoparasiticides |
| SE7110610A SE372530B (enExample) | 1970-08-22 | 1971-08-20 | |
| ZA715577A ZA715577B (en) | 1970-08-22 | 1971-08-20 | Carbamates of 2-phenylhydrazino-2-imidazolines,processes for their use as ectoparasiticides |
| GB3939671A GB1308278A (en) | 1970-08-22 | 1971-08-28 | Carbazine acid esters and salts thereof processes for their manu facture and their use as ectoparasiticides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702041734 DE2041734A1 (de) | 1970-08-22 | 1970-08-22 | Carbamate der 2-Phenylhydrazino-2-imidazoline,Verfahren zu ihrer Herstellung und ihre Verwendung als Ektoparasitizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2041734A1 true DE2041734A1 (de) | 1972-02-24 |
Family
ID=5780459
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702041734 Pending DE2041734A1 (de) | 1970-08-22 | 1970-08-22 | Carbamate der 2-Phenylhydrazino-2-imidazoline,Verfahren zu ihrer Herstellung und ihre Verwendung als Ektoparasitizide |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3755351A (enExample) |
| AT (1) | AT316577B (enExample) |
| AU (1) | AU462408B2 (enExample) |
| BE (1) | BE771583A (enExample) |
| CA (1) | CA939360A (enExample) |
| DE (1) | DE2041734A1 (enExample) |
| DK (1) | DK130904B (enExample) |
| FR (1) | FR2104611A5 (enExample) |
| GB (1) | GB1308278A (enExample) |
| IL (1) | IL37534A (enExample) |
| NL (1) | NL7111460A (enExample) |
| SE (1) | SE372530B (enExample) |
| ZA (1) | ZA715577B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4226876A (en) * | 1976-12-20 | 1980-10-07 | Burroughs Wellcome Co. | Arthropodicidal imidazoline derivatives |
| US5567723A (en) | 1995-07-05 | 1996-10-22 | Uniroyal Chemical Company, Inc. | Miticidal hydrazine compounds and their intermediates |
| KR20030010732A (ko) * | 2000-06-16 | 2003-02-05 | 소시에떼 드 테크놀로지 미쉐린 | 다작용성 폴리오가노실록산을 커플링제로서 포함하는타이어용 고무 조성물 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI48082C (fi) * | 1966-08-05 | 1974-06-10 | Boehringer Sohn Ingelheim | Menetelmä uusien verenpainetta alentavien 2-aryylihydratsino-imidatsol iinien-(2) valmistamiseksi |
| CH495995A (de) * | 1966-09-23 | 1970-09-15 | Ciba Geigy | Verfahren zur Herstellung neuer Hydrazinverbindungen |
| DE1670184A1 (de) * | 1967-01-20 | 1971-01-21 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung heterocyclisch substituierter Hydrazino-imidazoline-(2) |
-
1970
- 1970-08-22 DE DE19702041734 patent/DE2041734A1/de active Pending
-
1971
- 1971-08-19 NL NL7111460A patent/NL7111460A/xx unknown
- 1971-08-19 US US00173290A patent/US3755351A/en not_active Expired - Lifetime
- 1971-08-20 AU AU32609/71A patent/AU462408B2/en not_active Expired
- 1971-08-20 ZA ZA715577A patent/ZA715577B/xx unknown
- 1971-08-20 AT AT731571A patent/AT316577B/de active
- 1971-08-20 SE SE7110610A patent/SE372530B/xx unknown
- 1971-08-20 IL IL37534A patent/IL37534A/xx unknown
- 1971-08-20 BE BE771583A patent/BE771583A/xx unknown
- 1971-08-20 FR FR7130452A patent/FR2104611A5/fr not_active Expired
- 1971-08-20 DK DK410371AA patent/DK130904B/da unknown
- 1971-08-20 CA CA121,016A patent/CA939360A/en not_active Expired
- 1971-08-28 GB GB3939671A patent/GB1308278A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK130904C (enExample) | 1975-10-06 |
| US3755351A (en) | 1973-08-28 |
| DK130904B (da) | 1975-05-05 |
| GB1308278A (en) | 1973-02-21 |
| CA939360A (en) | 1974-01-01 |
| SE372530B (enExample) | 1974-12-23 |
| FR2104611A5 (enExample) | 1972-04-14 |
| AU462408B2 (en) | 1975-06-26 |
| IL37534A (en) | 1974-07-31 |
| ZA715577B (en) | 1972-04-26 |
| AT316577B (de) | 1974-07-25 |
| NL7111460A (enExample) | 1972-02-24 |
| IL37534A0 (en) | 1971-11-29 |
| BE771583A (fr) | 1972-02-21 |
| AU3260971A (en) | 1973-02-22 |
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