DE2531606A1 - Substituierte 2-phenylimino-thiazoline, verfahren zu ihrer herstellung sowie ihre verwendung als ektoparasitizide - Google Patents
Substituierte 2-phenylimino-thiazoline, verfahren zu ihrer herstellung sowie ihre verwendung als ektoparasitizideInfo
- Publication number
- DE2531606A1 DE2531606A1 DE19752531606 DE2531606A DE2531606A1 DE 2531606 A1 DE2531606 A1 DE 2531606A1 DE 19752531606 DE19752531606 DE 19752531606 DE 2531606 A DE2531606 A DE 2531606A DE 2531606 A1 DE2531606 A1 DE 2531606A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- methyl
- carbon atoms
- thiazoline
- phenylimino
- 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
- BYDJIMNNZMJUII-UHFFFAOYSA-N n-phenyl-5h-1,3-thiazol-2-imine Chemical class N1=CCSC1=NC1=CC=CC=C1 BYDJIMNNZMJUII-UHFFFAOYSA-N 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 241001465754 Metazoa Species 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 claims description 7
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 244000078703 ectoparasite Species 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000001984 ectoparasiticidal effect Effects 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- -1 crotyl Chemical group 0.000 description 36
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000004480 active ingredient Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 230000000694 effects Effects 0.000 description 16
- 241000238876 Acari Species 0.000 description 15
- 230000018109 developmental process Effects 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 241000283690 Bos taurus Species 0.000 description 9
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 5
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- HZAOAIZJMMTSFN-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)-3-methylthiourea Chemical compound CNC(=S)NC1=CC=C(C)C=C1C HZAOAIZJMMTSFN-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
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- 239000003995 emulsifying agent Substances 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
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- WANFDKZEUCWCEP-UHFFFAOYSA-N 1-methyl-3-(2,4,5-trimethylphenyl)thiourea Chemical compound CNC(=S)NC1=CC(C)=C(C)C=C1C WANFDKZEUCWCEP-UHFFFAOYSA-N 0.000 description 3
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000013057 ectoparasiticide Substances 0.000 description 3
- 230000003071 parasitic effect Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000003549 thiazolines Chemical class 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
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- BMIPMKQAAJKBKP-UHFFFAOYSA-N 2,4,5-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C=C1C BMIPMKQAAJKBKP-UHFFFAOYSA-N 0.000 description 2
- NMPVEAUIHMEAQP-UHFFFAOYSA-N 2-Bromoacetaldehyde Chemical compound BrCC=O NMPVEAUIHMEAQP-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000819999 Nymphes Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- 235000015278 beef Nutrition 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- UKJYMWCKWMUEMH-UHFFFAOYSA-N n-(4-ethyl-2-methylphenyl)-3-methyl-1,3-thiazol-2-imine Chemical compound CC1=CC(CC)=CC=C1N=C1N(C)C=CS1 UKJYMWCKWMUEMH-UHFFFAOYSA-N 0.000 description 2
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- 238000005516 engineering process Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 201000002266 mite infestation Diseases 0.000 description 1
- IVNKNYXSKGYEIK-UHFFFAOYSA-N n-(2,4-dimethylphenyl)-3-ethyl-1,3-thiazol-2-imine Chemical compound CCN1C=CSC1=NC1=CC=C(C)C=C1C IVNKNYXSKGYEIK-UHFFFAOYSA-N 0.000 description 1
- YUAUPYJCVKNAEC-UHFFFAOYSA-N n-(2,4-dimethylphenyl)-3-methyl-1,3-thiazol-2-imine Chemical compound CC1=CC(C)=CC=C1N=C1N(C)C=CS1 YUAUPYJCVKNAEC-UHFFFAOYSA-N 0.000 description 1
- MNKSOMXENBXQFR-UHFFFAOYSA-N n-(2,4-dimethylphenyl)-3-propyl-1,3-thiazol-2-imine Chemical compound CCCN1C=CSC1=NC1=CC=C(C)C=C1C MNKSOMXENBXQFR-UHFFFAOYSA-N 0.000 description 1
- WPVRKNZMQWRZCK-UHFFFAOYSA-N n-(2-ethyl-4-methylphenyl)-3-methyl-1,3-thiazol-2-imine Chemical compound CCC1=CC(C)=CC=C1N=C1N(C)C=CS1 WPVRKNZMQWRZCK-UHFFFAOYSA-N 0.000 description 1
- HTIBIRSDPULMLP-UHFFFAOYSA-N n-(4-chloro-2,5-dimethylphenyl)-3-methyl-1,3-thiazol-2-imine Chemical compound C1=C(Cl)C(C)=CC(N=C2N(C=CS2)C)=C1C HTIBIRSDPULMLP-UHFFFAOYSA-N 0.000 description 1
- CYSKDXFVYLPFOP-UHFFFAOYSA-N n-(5-chloro-2,4-dimethylphenyl)-3-methyl-1,3-thiazol-2-imine Chemical compound C1=C(Cl)C(C)=CC(C)=C1N=C1N(C)C=CS1 CYSKDXFVYLPFOP-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 231100000194 ovacidal Toxicity 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 238000009304 pastoral farming Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical class S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 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
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752531606 DE2531606A1 (de) | 1975-07-15 | 1975-07-15 | Substituierte 2-phenylimino-thiazoline, verfahren zu ihrer herstellung sowie ihre verwendung als ektoparasitizide |
| EG76420A EG12318A (en) | 1975-07-15 | 1976-07-10 | Method for preparation of substituted(2-methylamino)thiazolin and uses as parasiticide |
| NZ181435A NZ181435A (en) | 1975-07-15 | 1976-07-12 | 2-(2,4-dialkylphenylimino)-thiazolines |
| GB29105/76A GB1505020A (en) | 1975-07-15 | 1976-07-13 | Substituted 2-phenylimino-thiazolines a process for their preparation and their use as ectoparasiticides |
| BE168856A BE844065A (fr) | 1975-07-15 | 1976-07-13 | Nouvelles 2-phenylimino-thiazolines substituees, leur procede de preparation et compositions ectoparasiticides les contenant |
| AU15847/76A AU498662B2 (en) | 1975-07-15 | 1976-07-14 | 2-phenylimino-thiazolines & their use as ectoparasiticides |
| ZA764173A ZA764173B (en) | 1975-07-15 | 1976-07-14 | Substituted 2-phenylimino-thiaxolines a process for their preparation and their use as ectoparasiticides |
| ES449817A ES449817A1 (es) | 1975-07-15 | 1976-07-14 | Procedimiento para producir 2-fenilamino-tiazolinas susti- tuidas. |
| NL7607856A NL7607856A (nl) | 1975-07-15 | 1976-07-15 | Werkwijze voor het bereiden van gesubstitueerde 2-fenyliminothiazolinen, alsmede bereiding van preparaten voor het bestrijden van ectoparasie- ten op basis daarvan, alsmede de toepassing daarvan als ectoparasiticiden. |
| FR7621657A FR2317926A1 (fr) | 1975-07-15 | 1976-07-15 | Nouvelles 2-phenylimino-thiazolines substituees, leur procede de preparation et compositions ectoparasiticides les contenant |
| AR263958A AR211546A1 (es) | 1975-07-15 | 1976-07-15 | Procedimiento para la produccion de nuevas 2-fenilimino-tiazolinas substituidas y sus sales |
| KE2879A KE2879A (en) | 1975-07-15 | 1978-09-08 | Substituted 2-phyenylimon-thiazolines, a process for their preparation and their use as ectoparasiticides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752531606 DE2531606A1 (de) | 1975-07-15 | 1975-07-15 | Substituierte 2-phenylimino-thiazoline, verfahren zu ihrer herstellung sowie ihre verwendung als ektoparasitizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2531606A1 true DE2531606A1 (de) | 1977-02-03 |
Family
ID=5951566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752531606 Pending DE2531606A1 (de) | 1975-07-15 | 1975-07-15 | Substituierte 2-phenylimino-thiazoline, verfahren zu ihrer herstellung sowie ihre verwendung als ektoparasitizide |
Country Status (12)
| Country | Link |
|---|---|
| AR (1) | AR211546A1 (enExample) |
| AU (1) | AU498662B2 (enExample) |
| BE (1) | BE844065A (enExample) |
| DE (1) | DE2531606A1 (enExample) |
| EG (1) | EG12318A (enExample) |
| ES (1) | ES449817A1 (enExample) |
| FR (1) | FR2317926A1 (enExample) |
| GB (1) | GB1505020A (enExample) |
| KE (1) | KE2879A (enExample) |
| NL (1) | NL7607856A (enExample) |
| NZ (1) | NZ181435A (enExample) |
| ZA (1) | ZA764173B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0683160A1 (en) * | 1994-04-04 | 1995-11-22 | Sumitomo Chemical Company, Limited | Iminothiazoline derivatives and herbicides containing them as active ingredients |
| WO2000034256A1 (de) * | 1998-12-10 | 2000-06-15 | Bayer Aktiengesellschaft | Substituierte 2-imino-thiazoline |
| WO2005089550A3 (de) * | 2004-03-19 | 2005-11-10 | Bayer Healthcare Ag | Parasitizide mittel |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2618560A1 (de) * | 1976-04-28 | 1977-11-10 | Bayer Ag | Substituierte 2-phenylimino-thiazoline, verfahren zu ihrer herstellung sowie ihre verwendung als ektoparasitizide |
| FI73864C (fi) * | 1983-04-14 | 1987-12-10 | Ciba Geigy Ag | Foerfarande och sockerhaltigt medel foer bekaempning av biparasitkvalster. |
| CN106432131B (zh) * | 2016-09-22 | 2018-06-05 | 青岛科技大学 | 一种三亚胺噻唑衍生物的制备方法 |
-
1975
- 1975-07-15 DE DE19752531606 patent/DE2531606A1/de active Pending
-
1976
- 1976-07-10 EG EG76420A patent/EG12318A/xx active
- 1976-07-12 NZ NZ181435A patent/NZ181435A/xx unknown
- 1976-07-13 GB GB29105/76A patent/GB1505020A/en not_active Expired
- 1976-07-13 BE BE168856A patent/BE844065A/xx unknown
- 1976-07-14 ES ES449817A patent/ES449817A1/es not_active Expired
- 1976-07-14 ZA ZA764173A patent/ZA764173B/xx unknown
- 1976-07-14 AU AU15847/76A patent/AU498662B2/en not_active Expired
- 1976-07-15 FR FR7621657A patent/FR2317926A1/fr active Granted
- 1976-07-15 NL NL7607856A patent/NL7607856A/xx not_active Application Discontinuation
- 1976-07-15 AR AR263958A patent/AR211546A1/es active
-
1978
- 1978-09-08 KE KE2879A patent/KE2879A/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0683160A1 (en) * | 1994-04-04 | 1995-11-22 | Sumitomo Chemical Company, Limited | Iminothiazoline derivatives and herbicides containing them as active ingredients |
| US5521145A (en) * | 1994-04-04 | 1996-05-28 | Sumitomo Chemical Company, Ltd. | Iminothiazoline derivatives and herbicides containing them as active ingredients |
| WO2000034256A1 (de) * | 1998-12-10 | 2000-06-15 | Bayer Aktiengesellschaft | Substituierte 2-imino-thiazoline |
| WO2005089550A3 (de) * | 2004-03-19 | 2005-11-10 | Bayer Healthcare Ag | Parasitizide mittel |
Also Published As
| Publication number | Publication date |
|---|---|
| AU1584776A (en) | 1978-01-19 |
| NL7607856A (nl) | 1977-01-18 |
| KE2879A (en) | 1978-09-22 |
| FR2317926A1 (fr) | 1977-02-11 |
| BE844065A (fr) | 1977-01-13 |
| ES449817A1 (es) | 1977-08-01 |
| AU498662B2 (en) | 1979-03-22 |
| FR2317926B1 (enExample) | 1978-11-17 |
| EG12318A (en) | 1978-12-31 |
| ZA764173B (en) | 1977-06-29 |
| NZ181435A (en) | 1978-04-28 |
| GB1505020A (en) | 1978-03-22 |
| AR211546A1 (es) | 1978-01-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |