DE4121208A1 - 2-(4-substituierte phenylhydrazino)-2-thiazoline und 2-(4-substituierte phenylazo)-2-thiazoline, ihre herstellung und ihre verwendung zur bekaempfung von ektoparasiten - Google Patents
2-(4-substituierte phenylhydrazino)-2-thiazoline und 2-(4-substituierte phenylazo)-2-thiazoline, ihre herstellung und ihre verwendung zur bekaempfung von ektoparasitenInfo
- Publication number
- DE4121208A1 DE4121208A1 DE4121208A DE4121208A DE4121208A1 DE 4121208 A1 DE4121208 A1 DE 4121208A1 DE 4121208 A DE4121208 A DE 4121208A DE 4121208 A DE4121208 A DE 4121208A DE 4121208 A1 DE4121208 A1 DE 4121208A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- thiazoline
- halogen
- spp
- thiazolines
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
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- -1 2- (4-SUBSTITUTED PHENYLHYDRAZINO) -2-THIAZOLINE Chemical class 0.000 title description 82
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 150000004031 phenylhydrazines Chemical class 0.000 claims description 11
- 150000003549 thiazolines Chemical class 0.000 claims description 11
- 229910004013 NO 2 Inorganic materials 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 244000078703 ectoparasite Species 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims description 3
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- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000004544 spot-on Substances 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- AWDBHOZBRXWRKS-UHFFFAOYSA-N tetrapotassium;iron(6+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+6].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] AWDBHOZBRXWRKS-UHFFFAOYSA-N 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
- C07D277/18—Nitrogen atoms
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Public Health (AREA)
- Agronomy & Crop Science (AREA)
- Medicinal Chemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4121208A DE4121208A1 (de) | 1991-06-27 | 1991-06-27 | 2-(4-substituierte phenylhydrazino)-2-thiazoline und 2-(4-substituierte phenylazo)-2-thiazoline, ihre herstellung und ihre verwendung zur bekaempfung von ektoparasiten |
| TW081104159A TW198716B (enExample) | 1991-06-27 | 1992-05-28 | |
| AU18032/92A AU1803292A (en) | 1991-06-27 | 1992-06-04 | 2-(4-substituted phenylhydrazino)-2-thiazolines and 2-(4-substituted phenylazo)-2-thiazolines, their preparation, and their use for combating ectoparasites |
| EP19920110040 EP0520274A3 (en) | 1991-06-27 | 1992-06-15 | 2-(-4-substituted-phenylhydrazino)-2-thiazoline and 2-(-4-substituted phenylazo)-2-thiazoline, their preparation and their use against ectoparasites |
| JP4187351A JPH05186443A (ja) | 1991-06-27 | 1992-06-23 | ２−（４−置換フエニルヒドラジノ）−２−チアゾリン及び２−（４−置換フエニルアゾ）−２−チアゾリン、それらの製造方法及び体外寄生虫を駆除するための利用 |
| CA002072217A CA2072217A1 (en) | 1991-06-27 | 1992-06-24 | 2-(4-substituted phenylhydrazino)-2-thiazolines and 2-(4-substituted phenylazo)-2-thiazolines, their preparation, and their use for combating ectoparasites |
| ZA924745A ZA924745B (en) | 1991-06-27 | 1992-06-26 | 2-(4-substituted phenylhydrazino)-2-thiazolines and 2-(4-substituted phenylaza)-2-thiazolines,their preparation,and their use for combating ectoparasites |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4121208A DE4121208A1 (de) | 1991-06-27 | 1991-06-27 | 2-(4-substituierte phenylhydrazino)-2-thiazoline und 2-(4-substituierte phenylazo)-2-thiazoline, ihre herstellung und ihre verwendung zur bekaempfung von ektoparasiten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4121208A1 true DE4121208A1 (de) | 1993-01-14 |
Family
ID=6434850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4121208A Withdrawn DE4121208A1 (de) | 1991-06-27 | 1991-06-27 | 2-(4-substituierte phenylhydrazino)-2-thiazoline und 2-(4-substituierte phenylazo)-2-thiazoline, ihre herstellung und ihre verwendung zur bekaempfung von ektoparasiten |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0520274A3 (enExample) |
| JP (1) | JPH05186443A (enExample) |
| AU (1) | AU1803292A (enExample) |
| CA (1) | CA2072217A1 (enExample) |
| DE (1) | DE4121208A1 (enExample) |
| TW (1) | TW198716B (enExample) |
| ZA (1) | ZA924745B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9108932B2 (en) | 2013-03-13 | 2015-08-18 | Dow Agrosciences Llc | Preparation of haloalkoxyarylhydrazines and intermediates therefrom |
| BR112016008070B8 (pt) | 2013-10-17 | 2022-08-23 | Dow Agrosciences Llc | Compostos pesticidas, e seus processos de preparação |
| WO2018125817A1 (en) | 2016-12-29 | 2018-07-05 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4046753A (en) * | 1973-10-11 | 1977-09-06 | Merck & Co., Inc. | Substituted 2-phenylhydrazino and 2-phenylazo thiazolines |
| HU168777B (enExample) * | 1973-12-04 | 1976-07-28 | ||
| DE3133918A1 (de) * | 1981-08-27 | 1983-03-17 | Bayer Ag, 5090 Leverkusen | 2-arylhydrazino-2-thiazoline, acylderivate derselben, 2-arylazo-2-thiazoline, herstellungsverfahren und ihre verwendung zur bekaempfung von ekto- und endoparasiten |
-
1991
- 1991-06-27 DE DE4121208A patent/DE4121208A1/de not_active Withdrawn
-
1992
- 1992-05-28 TW TW081104159A patent/TW198716B/zh active
- 1992-06-04 AU AU18032/92A patent/AU1803292A/en not_active Abandoned
- 1992-06-15 EP EP19920110040 patent/EP0520274A3/de not_active Withdrawn
- 1992-06-23 JP JP4187351A patent/JPH05186443A/ja active Pending
- 1992-06-24 CA CA002072217A patent/CA2072217A1/en not_active Abandoned
- 1992-06-26 ZA ZA924745A patent/ZA924745B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0520274A2 (de) | 1992-12-30 |
| JPH05186443A (ja) | 1993-07-27 |
| EP0520274A3 (en) | 1993-03-03 |
| CA2072217A1 (en) | 1992-12-28 |
| AU1803292A (en) | 1993-01-07 |
| ZA924745B (en) | 1993-03-31 |
| TW198716B (enExample) | 1993-01-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |